#------------------------------------------------------------------------------ #$Date: 2019-11-08 02:16:29 +0200 (Fri, 08 Nov 2019) $ #$Revision: 224707 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/85/7058505.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7058505 loop_ _publ_author_name 'Dubovtsev, Alexey Yu.' 'Ivanov, Daniil M.' 'Dabranskaya, Uladzislava' 'Bokach, Nadezhda A.' 'Kukushkin, Vadim Yu.' _publ_section_title ; Saccharin guanidination via facile three-component “two saccharins-one dialkylcyanamide” integration ; _journal_issue 27 _journal_name_full 'New Journal of Chemistry' _journal_page_first 10685 _journal_paper_doi 10.1039/C9NJ02656H _journal_volume 43 _journal_year 2019 _chemical_formula_moiety '2(C19 H20 N4 O6 S2), C5 H10 N2' _chemical_formula_sum 'C43 H50 N10 O12 S4' _chemical_formula_weight 1027.17 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2017-01-26 _audit_creation_method ; Olex2 1.2 (compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267) ; _audit_update_record ; 2019-05-20 deposited with the CCDC. 2019-06-18 downloaded from the CCDC. ; _cell_angle_alpha 84.309(4) _cell_angle_beta 84.453(4) _cell_angle_gamma 80.817(4) _cell_formula_units_Z 2 _cell_length_a 8.0019(4) _cell_length_b 15.8441(8) _cell_length_c 20.2939(9) _cell_measurement_reflns_used 10332 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.5310 _cell_measurement_theta_min 3.0170 _cell_volume 2518.9(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.2096 _diffrn_measured_fraction_theta_full 0.9993 _diffrn_measured_fraction_theta_max 0.8860 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -47.00 36.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 38.0000 60.0000 83 #__ type_ start__ end____ width___ exp.time_ 2 omega 15.00 46.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 57.0000 60.0000 31 #__ type_ start__ end____ width___ exp.time_ 3 omega -48.00 42.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 38.0000 -30.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega -72.00 11.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 112.0000 58.0000 83 #__ type_ start__ end____ width___ exp.time_ 5 omega -92.00 6.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 -77.0000 -180.0000 98 #__ type_ start__ end____ width___ exp.time_ 6 omega 29.00 65.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 23.3616 -99.0000 -30.0000 36 #__ type_ start__ end____ width___ exp.time_ 7 omega -21.00 6.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 23.3616 -99.0000 -30.0000 27 #__ type_ start__ end____ width___ exp.time_ 8 omega -62.00 -2.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 0.0000 -30.0000 60 #__ type_ start__ end____ width___ exp.time_ 9 omega -91.00 8.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 -77.0000 30.0000 99 #__ type_ start__ end____ width___ exp.time_ 10 omega -91.00 -1.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 -57.0000 -90.0000 90 #__ type_ start__ end____ width___ exp.time_ 11 omega -36.00 -2.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - -22.4241 -57.0000 60.0000 34 #__ type_ start__ end____ width___ exp.time_ 12 omega -47.00 53.00 1.0000 25.0000 omega____ theta____ kappa____ phi______ frames - 23.3616 -77.0000 -180.0000 100 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0184639000 _diffrn_orient_matrix_UB_12 -0.0060859000 _diffrn_orient_matrix_UB_13 0.0337838000 _diffrn_orient_matrix_UB_21 -0.0669729000 _diffrn_orient_matrix_UB_22 -0.0247218000 _diffrn_orient_matrix_UB_23 0.0074626000 _diffrn_orient_matrix_UB_31 0.0573698000 _diffrn_orient_matrix_UB_32 -0.0377274000 _diffrn_orient_matrix_UB_33 -0.0067162000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.884 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 47338 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.884 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.155 _diffrn_reflns_theta_min 2.700 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92584 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.354 _exptl_crystal_description prism _exptl_crystal_F_000 1076 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _platon_squeeze_details ; ; _refine_diff_density_max 0.608 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.071 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 638 _refine_ls_number_reflns 14394 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0489 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+1.8212P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1143 _refine_ls_wR_factor_ref 0.1218 _reflns_Friedel_coverage 0.000 _reflns_number_gt 11387 _reflns_number_total 14394 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj02656h2.cif _cod_data_source_block 0dv-23-11-1 _cod_depositor_comments 'Adding full bibliography for 7058503--7058505.cif.' _cod_database_code 7058505 _chemical_oxdiff_formula 'C20 H22 N6 O6 S2' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.93 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.51 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C17B-C16A = C17A-C16A 1.52 with sigma of 0.002 3. Others Fixed Sof: H16A(0.55) H16B(0.55) H16C(0.45) H16D(0.45) C17A(0.55) H17A(0.55) H17B(0.55) H17C(0.55) C17B(0.45) H1BA(0.45) H1BB(0.45) H1BC(0.45) 4.a Secondary CH2 refined with riding coordinates: C18(H18C,H18D), C16(H16E,H16F), C18A(H18A,H18B), C16A(H16A,H16B), C16A(H16C, H16D), C4S(H4SA,H4SB), C2S(H2SA,H2SB) 4.b Aromatic/amide H refined with riding coordinates: C12(H12), C11(H11), C4A(H4A), C2A(H2A), C9A(H9A), C5A(H5A), C5(H5), C12A(H12A), C9(H9), C10(H10), C11A(H11A), C4(H4), C2(H2), C10A(H10A), C3A(H3A), C3(H3) 4.c X=CH2 refined with riding coordinates: N3(H3B,H3C), N3A(H3AA,H3AB) 4.d Idealised Me refined as rotating group: C19(H19D,H19E,H19F), C17(H17D,H17E,H17F), C19A(H19A,H19B,H19C), C3S(H3SA,H3SB, H3SC), C5S(H5SA,H5SB,H5SC), C17A(H17A,H17B,H17C), C17B(H1BA,H1BB,H1BC) ; _shelx_res_file ; 0dv-23-11-1.res created by SHELXL-2014/7 TITL 0dv-23-11-1_a.res in P-1 REM Old TITL DV-23-11-1 in P-1 REM SHELXT solution in P-1 REM R1 0.141, Rweak 0.005, Alpha 0.048, Orientation as input REM Formula found by SHELXT: C44 N9 O13 S4 CELL 0.71073 8.0019 15.8441 20.2939 84.309 84.453 80.817 ZERR 2 0.0004 0.0008 0.0009 0.004 0.004 0.004 LATT 1 SFAC C H N O S UNIT 86 100 20 24 8 DFIX 1.52 0.002 C17B C16A C17A C16A L.S. 4 PLAN 25 BOND $H list 4 fmap 2 ACTA OMIT 0 -2 1 OMIT 0 2 0 OMIT 0 1 4 OMIT 0 1 3 OMIT 0 -1 3 OMIT 0 0 3 OMIT 9 0 8 OMIT -8 11 2 OMIT -4 -20 1 OMIT 1 -8 2 OMIT 0 0 4 OMIT 6 -15 4 OMIT 10 -5 8 OMIT 9 -2 5 OMIT 1 1 0 OMIT 1 -1 1 OMIT -2 6 0 OMIT 3 13 2 OMIT -1 1 3 OMIT -6 14 0 OMIT 10 0 3 OMIT 0 3 1 OMIT 1 0 2 OMIT -7 8 5 OMIT 2 7 4 REM REM REM WGHT 0.051800 1.821200 FVAR 3.28104 S2A 5 0.559675 0.510894 0.281656 11.00000 0.00980 0.01093 = 0.02095 -0.00201 0.00069 -0.00182 S1 5 0.825161 -0.031494 0.353858 11.00000 0.01426 0.01052 = 0.01775 -0.00183 -0.00191 -0.00261 S2 5 0.957686 0.182278 0.194777 11.00000 0.00834 0.01192 = 0.02714 -0.00023 -0.00100 -0.00241 S1A 5 0.676971 0.730238 0.131288 11.00000 0.02126 0.01125 = 0.01844 -0.00275 0.00118 -0.00202 O3 4 0.789983 -0.020631 0.167677 11.00000 0.02153 0.01449 = 0.01928 -0.00125 -0.00203 -0.00198 O3A 4 0.742883 0.713153 0.315265 11.00000 0.02053 0.01287 = 0.02175 -0.00230 -0.00053 -0.00369 O6 4 1.027344 0.247659 0.149449 11.00000 0.01440 0.01377 = 0.02772 -0.00276 0.00236 -0.00665 O6A 4 0.485837 0.447807 0.327962 11.00000 0.01379 0.01182 = 0.02750 -0.00083 0.00099 -0.00476 O5A 4 0.466451 0.596954 0.284116 11.00000 0.01317 0.01208 = 0.03693 -0.00086 -0.00325 0.00035 O2 4 0.682447 -0.059210 0.392769 11.00000 0.01937 0.01853 = 0.02046 -0.00049 0.00284 -0.00429 O1 4 0.923908 0.021831 0.381133 11.00000 0.02260 0.01611 = 0.02693 -0.00581 -0.00732 -0.00444 O4A 4 0.594063 0.484094 0.214374 11.00000 0.01545 0.03232 = 0.02295 -0.00731 0.00026 -0.00299 O5 4 1.058763 0.098116 0.192517 11.00000 0.01158 0.01314 = 0.05516 -0.00049 -0.00674 0.00016 O1A 4 0.574866 0.676583 0.106357 11.00000 0.03246 0.01975 = 0.02531 -0.00867 -0.00386 -0.00587 O2A 4 0.811628 0.760693 0.089141 11.00000 0.03065 0.01603 = 0.02496 0.00062 0.00893 -0.00307 O4 4 0.916649 0.207327 0.262203 11.00000 0.01306 0.03556 = 0.02599 -0.00137 -0.00249 -0.00629 N1 3 0.765459 0.014426 0.277581 11.00000 0.01331 0.00855 = 0.01764 -0.00070 -0.00138 -0.00079 N4 3 0.337653 0.211550 0.348075 11.00000 0.01400 0.01143 = 0.02177 -0.00328 -0.00039 -0.00179 N2 3 0.592716 0.120143 0.329249 11.00000 0.01044 0.01133 = 0.02412 -0.00173 -0.00150 -0.00117 N1A 3 0.751418 0.682669 0.204611 11.00000 0.01773 0.00898 = 0.01932 -0.00197 0.00190 -0.00118 N4A 3 1.165944 0.488094 0.118952 11.00000 0.01737 0.01344 = 0.02342 -0.00356 0.00373 -0.00449 N3 3 0.588764 0.267841 0.318637 11.00000 0.01359 0.01091 = 0.03135 -0.00377 0.00145 -0.00158 AFIX 93 H3B 2 0.538195 0.319449 0.322529 11.00000 -1.20000 H3C 2 0.695951 0.258467 0.307151 11.00000 -1.20000 AFIX 0 N3A 3 0.917556 0.431633 0.154178 11.00000 0.01538 0.01246 = 0.02793 -0.00468 0.00490 -0.00167 AFIX 93 H3AA 2 0.965574 0.380593 0.146565 11.00000 -1.20000 H3AB 2 0.812782 0.440497 0.169461 11.00000 -1.20000 AFIX 0 N2A 3 0.918018 0.578830 0.148973 11.00000 0.02195 0.00971 = 0.02510 -0.00228 0.00585 -0.00198 N2S 3 0.393281 0.719513 0.462600 11.00000 0.03078 0.02681 = 0.02705 0.00015 -0.00448 -0.01330 C13 1 0.632283 0.138299 0.206571 11.00000 0.01280 0.00666 = 0.02166 -0.00245 -0.00028 -0.00153 C7A 1 0.693943 0.730521 0.260856 11.00000 0.01445 0.00937 = 0.02085 -0.00353 0.00324 -0.00511 C7 1 0.829108 -0.035997 0.223492 11.00000 0.01181 0.00933 = 0.02000 -0.00162 0.00146 -0.00400 C15 1 0.501698 0.202895 0.330313 11.00000 0.01366 0.01213 = 0.01842 -0.00346 -0.00188 0.00002 C6 1 0.945744 -0.111786 0.249720 11.00000 0.01136 0.00824 = 0.02217 -0.00031 -0.00137 -0.00299 C14 1 0.661525 0.094060 0.273720 11.00000 0.01021 0.00863 = 0.02291 -0.00165 -0.00127 -0.00375 C8A 1 0.763392 0.513581 0.309933 11.00000 0.01031 0.01080 = 0.02232 -0.00306 0.00087 -0.00147 C14A 1 0.854343 0.602856 0.205428 11.00000 0.01363 0.00857 = 0.02527 -0.00128 0.00204 -0.00452 C6A 1 0.571378 0.805655 0.239055 11.00000 0.01331 0.01051 = 0.02251 -0.00321 0.00121 -0.00478 C1 1 0.954472 -0.117482 0.317873 11.00000 0.01207 0.00887 = 0.02315 -0.00182 -0.00148 -0.00233 C13A 1 0.885807 0.556017 0.271516 11.00000 0.01265 0.00849 = 0.02271 -0.00324 0.00147 -0.00111 C12 1 0.470850 0.142270 0.184540 11.00000 0.01258 0.01078 = 0.02344 -0.00251 0.00072 -0.00327 AFIX 43 H12 2 0.386098 0.120057 0.212339 11.00000 -1.20000 AFIX 0 C11 1 0.436139 0.179148 0.121442 11.00000 0.01168 0.01684 = 0.02524 -0.00243 -0.00344 -0.00120 AFIX 43 H11 2 0.328600 0.181397 0.106977 11.00000 -1.20000 AFIX 0 C8 1 0.756979 0.175938 0.165678 11.00000 0.01020 0.00970 = 0.02566 -0.00104 -0.00065 -0.00055 C1A 1 0.551643 0.813774 0.171762 11.00000 0.01458 0.01162 = 0.02453 -0.00399 0.00163 -0.00374 C4A 1 0.371991 0.932973 0.250563 11.00000 0.01558 0.01285 = 0.03219 -0.00856 0.00301 -0.00430 AFIX 43 H4A 2 0.309260 0.973602 0.276883 11.00000 -1.20000 AFIX 0 C2A 1 0.444730 0.880704 0.141532 11.00000 0.01962 0.01542 = 0.02464 -0.00043 -0.00321 -0.00410 AFIX 43 H2A 2 0.433841 0.885387 0.096051 11.00000 -1.20000 AFIX 0 C9A 1 0.803460 0.471997 0.371204 11.00000 0.01507 0.01351 = 0.02454 0.00035 0.00140 -0.00307 AFIX 43 H9A 2 0.725588 0.441489 0.396153 11.00000 -1.20000 AFIX 0 C5A 1 0.481424 0.865851 0.279847 11.00000 0.01468 0.01392 = 0.02449 -0.00587 0.00190 -0.00609 AFIX 43 H5A 2 0.494135 0.861302 0.325190 11.00000 -1.20000 AFIX 0 C5 1 1.041411 -0.173758 0.211716 11.00000 0.01634 0.01063 = 0.02363 -0.00385 0.00192 -0.00356 AFIX 43 H5 2 1.035332 -0.171141 0.166009 11.00000 -1.20000 AFIX 0 C15A 1 1.004680 0.496377 0.142405 11.00000 0.01751 0.01354 = 0.01873 -0.00327 0.00240 -0.00158 C12A 1 1.043879 0.555513 0.294935 11.00000 0.01265 0.01125 = 0.03071 -0.00345 0.00176 -0.00415 AFIX 43 H12A 2 1.126335 0.581300 0.268462 11.00000 -1.20000 AFIX 0 C18 1 0.235036 0.297501 0.346049 11.00000 0.01369 0.01243 = 0.02773 -0.00434 -0.00119 0.00062 AFIX 23 H18C 2 0.291538 0.335758 0.367578 11.00000 -1.20000 H18D 2 0.125379 0.294139 0.370281 11.00000 -1.20000 AFIX 0 C9 1 0.721210 0.212825 0.102628 11.00000 0.01457 0.01546 = 0.02681 0.00307 0.00104 -0.00268 AFIX 43 H9 2 0.803656 0.237723 0.075436 11.00000 -1.20000 AFIX 0 C10 1 0.562375 0.212693 0.079940 11.00000 0.01665 0.01800 = 0.02426 0.00243 -0.00218 -0.00092 AFIX 43 H10 2 0.540831 0.235092 0.036951 11.00000 -1.20000 AFIX 0 C11A 1 1.079482 0.516811 0.357521 11.00000 0.01236 0.01578 = 0.03266 -0.00482 -0.00328 -0.00178 AFIX 43 H11A 2 1.183643 0.518704 0.373620 11.00000 -1.20000 AFIX 0 C4 1 1.146359 -0.239693 0.244709 11.00000 0.01379 0.00989 = 0.03382 -0.00532 0.00082 -0.00207 AFIX 43 H4 2 1.214427 -0.280819 0.220315 11.00000 -1.20000 AFIX 0 C2 1 1.053831 -0.184384 0.351781 11.00000 0.01795 0.01239 = 0.02468 0.00027 -0.00500 -0.00345 AFIX 43 H2 2 1.055170 -0.188356 0.397762 11.00000 -1.20000 AFIX 0 C16 1 0.245640 0.137180 0.365089 11.00000 0.01666 0.01367 = 0.02439 -0.00402 -0.00059 -0.00590 AFIX 23 H16E 2 0.313478 0.086477 0.347940 11.00000 -1.20000 H16F 2 0.139618 0.147863 0.344033 11.00000 -1.20000 AFIX 0 C10A 1 0.959076 0.475379 0.395842 11.00000 0.01626 0.01832 = 0.02503 -0.00065 -0.00268 -0.00039 AFIX 43 H10A 2 0.981868 0.449840 0.437941 11.00000 -1.20000 AFIX 0 C3A 1 0.354392 0.940601 0.182425 11.00000 0.01530 0.01110 = 0.03648 -0.00279 -0.00393 -0.00046 AFIX 43 H3A 2 0.281031 0.986502 0.164046 11.00000 -1.20000 AFIX 0 C18A 1 1.254252 0.404487 0.098731 11.00000 0.01515 0.01672 = 0.02456 -0.00505 0.00384 0.00039 AFIX 23 H18A 2 1.230791 0.359925 0.133154 11.00000 -1.20000 H18B 2 1.375784 0.405300 0.094435 11.00000 -1.20000 AFIX 0 N1S 3 0.104571 0.699415 0.512230 11.00000 0.03365 0.03546 = 0.06262 0.01909 -0.00329 -0.01130 C3 1 1.151893 -0.245563 0.313327 11.00000 0.01679 0.01005 = 0.03422 -0.00019 -0.00620 -0.00124 AFIX 43 H3 2 1.222039 -0.290969 0.333968 11.00000 -1.20000 AFIX 0 C19 1 0.209358 0.333539 0.274872 11.00000 0.02663 0.01458 = 0.03125 -0.00403 -0.01137 -0.00265 AFIX 137 H19D 2 0.167935 0.292135 0.251720 11.00000 -1.50000 H19E 2 0.315584 0.346011 0.253018 11.00000 -1.50000 H19F 2 0.128340 0.385229 0.274929 11.00000 -1.50000 AFIX 0 C17 1 0.208472 0.120843 0.439699 11.00000 0.03445 0.02450 = 0.02550 0.00011 -0.00377 -0.01605 AFIX 137 H17D 2 0.139410 0.076091 0.448782 11.00000 -1.50000 H17E 2 0.149201 0.172391 0.457335 11.00000 -1.50000 H17F 2 0.313317 0.103724 0.460127 11.00000 -1.50000 AFIX 0 C1S 1 0.240757 0.707878 0.491174 11.00000 0.03530 0.02403 = 0.03179 0.01031 -0.00849 -0.01006 C16A 1 1.261064 0.562003 0.108247 11.00000 0.01956 0.02046 = 0.03137 -0.00245 0.00197 -0.00926 PART 1 AFIX 23 H16A 2 1.365505 0.547832 0.130265 10.55000 -1.20000 H16B 2 1.193574 0.611100 0.127857 10.55000 -1.20000 AFIX 23 PART 0 PART 2 H16C 2 1.379501 0.541463 0.115027 10.45000 -1.20000 H16D 2 1.217624 0.601826 0.141411 10.45000 -1.20000 AFIX 0 PART 0 C19A 1 1.200198 0.382983 0.033275 11.00000 0.03005 0.02787 = 0.02587 -0.00841 0.00108 0.00269 AFIX 137 H19A 2 1.234854 0.423231 -0.001923 11.00000 -1.50000 H19B 2 1.078931 0.386141 0.036190 11.00000 -1.50000 H19C 2 1.252707 0.326012 0.024264 11.00000 -1.50000 AFIX 0 C4S 1 0.466131 0.792788 0.481591 11.00000 0.03457 0.03026 = 0.02996 -0.00123 -0.00540 -0.01540 AFIX 23 H4SA 2 0.563946 0.801752 0.451064 11.00000 -1.20000 H4SB 2 0.504907 0.779102 0.525771 11.00000 -1.20000 AFIX 0 C3S 1 0.617023 0.602266 0.504418 11.00000 0.03177 0.03869 = 0.02624 -0.00440 0.00233 -0.00408 AFIX 137 H3SA 2 0.680186 0.548031 0.493389 11.00000 -1.50000 H3SB 2 0.543006 0.593881 0.543863 11.00000 -1.50000 H3SC 2 0.694213 0.640182 0.512034 11.00000 -1.50000 AFIX 0 C5S 1 0.339983 0.874594 0.480947 11.00000 0.03934 0.03199 = 0.04249 -0.00958 0.00004 -0.01386 AFIX 137 H5SA 2 0.300288 0.888162 0.437436 11.00000 -1.50000 H5SB 2 0.393901 0.920576 0.492213 11.00000 -1.50000 H5SC 2 0.245572 0.867047 0.512783 11.00000 -1.50000 AFIX 0 C2S 1 0.512572 0.641164 0.447682 11.00000 0.04042 0.03147 = 0.02241 -0.00502 -0.00022 -0.01059 AFIX 23 H2SA 2 0.588958 0.654888 0.409424 11.00000 -1.20000 H2SB 2 0.448422 0.598705 0.435774 11.00000 -1.20000 AFIX 0 PART 1 C17A 1 1.302977 0.585226 0.034691 10.55000 0.04496 0.03157 = 0.03848 0.02093 -0.01835 -0.02276 AFIX 137 H17A 2 1.373854 0.537524 0.015611 10.55000 -1.50000 H17B 2 1.361758 0.634073 0.029250 10.55000 -1.50000 H17C 2 1.199793 0.598751 0.012750 10.55000 -1.50000 AFIX 0 PART 0 PART 2 C17B 1 1.250525 0.609912 0.039820 10.45000 0.06415 0.03555 = 0.05531 0.02760 -0.03610 -0.02929 AFIX 137 H1BA 2 1.291142 0.570873 0.006504 10.45000 -1.50000 H1BB 2 1.319120 0.654930 0.035879 10.45000 -1.50000 H1BC 2 1.134649 0.634226 0.033806 10.45000 -1.50000 AFIX 0 HKLF 4 REM 0dv-23-11-1_a.res in P-1 REM R1 = 0.0489 for 11387 Fo > 4sig(Fo) and 0.0643 for all 14394 data REM 638 parameters refined using 2 restraints END WGHT 0.0518 1.8212 REM Highest difference peak 0.608, deepest hole -0.414, 1-sigma level 0.071 Q1 1 0.5811 0.5089 0.2432 11.00000 0.05 0.61 Q2 1 0.6461 0.7719 0.2479 11.00000 0.05 0.52 Q3 1 0.8892 -0.0787 0.2385 11.00000 0.05 0.51 Q4 1 0.8167 -0.0177 0.3106 11.00000 0.05 0.47 Q5 1 0.6576 0.1104 0.2395 11.00000 0.05 0.45 Q6 1 0.3805 0.9324 0.2135 11.00000 0.05 0.44 Q7 1 0.9619 -0.1184 0.2823 11.00000 0.05 0.44 Q8 1 0.5591 0.1379 0.1939 11.00000 0.05 0.43 Q9 1 0.5542 0.8084 0.2058 11.00000 0.05 0.43 Q10 1 0.8505 0.5857 0.2452 11.00000 0.05 0.43 Q11 1 0.5199 0.4915 0.3191 11.00000 0.05 0.43 Q12 1 0.9123 -0.0716 0.3311 11.00000 0.05 0.42 Q13 1 0.7914 0.4888 0.3376 11.00000 0.05 0.42 Q14 1 0.4808 0.1605 0.1495 11.00000 0.05 0.42 Q15 1 0.5268 0.1563 0.3208 11.00000 0.05 0.41 Q16 1 1.1281 -0.2409 0.2808 11.00000 0.05 0.41 Q17 1 0.9451 0.1872 0.2371 11.00000 0.05 0.41 Q18 1 0.9629 0.5482 0.2810 11.00000 0.05 0.41 Q19 1 0.7796 -0.0418 0.3932 11.00000 0.05 0.41 Q20 1 0.2357 0.1341 0.4010 11.00000 0.05 0.40 Q21 1 0.6928 0.7176 0.1720 11.00000 0.05 0.40 Q22 1 0.7200 0.2035 0.1404 11.00000 0.05 0.39 Q23 1 1.0949 0.4890 0.1405 11.00000 0.05 0.39 Q24 1 0.7220 0.7329 0.0892 11.00000 0.05 0.39 Q25 1 0.5171 0.1864 0.1030 11.00000 0.05 0.39 ; _shelx_res_checksum 44193 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S2A S 0.55967(5) 0.51089(2) 0.28166(2) 0.01395(8) Uani 1 1 d . . . . S1 S 0.82516(5) -0.03149(2) 0.35386(2) 0.01401(8) Uani 1 1 d . . . . S2 S 0.95769(5) 0.18228(2) 0.19478(2) 0.01583(9) Uani 1 1 d . . . . S1A S 0.67697(6) 0.73024(3) 0.13129(2) 0.01712(9) Uani 1 1 d . . . . O3 O 0.78998(16) -0.02063(7) 0.16768(6) 0.0185(2) Uani 1 1 d . . . . O3A O 0.74288(16) 0.71315(7) 0.31527(6) 0.0183(2) Uani 1 1 d . . . . O6 O 1.02734(15) 0.24766(7) 0.14945(6) 0.0183(2) Uani 1 1 d . . . . O6A O 0.48584(15) 0.44781(7) 0.32796(6) 0.0176(2) Uani 1 1 d . . . . O5A O 0.46645(15) 0.59695(7) 0.28412(7) 0.0210(3) Uani 1 1 d . . . . O2 O 0.68245(16) -0.05921(8) 0.39277(6) 0.0197(2) Uani 1 1 d . . . . O1 O 0.92391(16) 0.02183(8) 0.38113(6) 0.0211(3) Uani 1 1 d . . . . O4A O 0.59406(16) 0.48409(9) 0.21437(6) 0.0234(3) Uani 1 1 d . . . . O5 O 1.05876(16) 0.09812(8) 0.19252(8) 0.0267(3) Uani 1 1 d . . . . O1A O 0.57487(18) 0.67658(8) 0.10636(7) 0.0251(3) Uani 1 1 d . . . . O2A O 0.81163(18) 0.76069(8) 0.08914(7) 0.0248(3) Uani 1 1 d . . . . O4 O 0.91665(16) 0.20733(9) 0.26220(7) 0.0246(3) Uani 1 1 d . . . . N1 N 0.76546(17) 0.01443(8) 0.27758(7) 0.0133(3) Uani 1 1 d . . . . N4 N 0.33765(18) 0.21155(9) 0.34808(7) 0.0157(3) Uani 1 1 d . . . . N2 N 0.59272(17) 0.12014(9) 0.32925(7) 0.0153(3) Uani 1 1 d . . . . N1A N 0.75142(18) 0.68267(8) 0.20461(7) 0.0156(3) Uani 1 1 d . . . . N4A N 1.16594(19) 0.48809(9) 0.11895(7) 0.0181(3) Uani 1 1 d . . . . N3 N 0.58876(18) 0.26784(9) 0.31864(8) 0.0187(3) Uani 1 1 d . . . . H3B H 0.5382 0.3194 0.3225 0.022 Uiso 1 1 calc R . . . H3C H 0.6960 0.2585 0.3072 0.022 Uiso 1 1 calc R . . . N3A N 0.91756(19) 0.43163(9) 0.15418(7) 0.0189(3) Uani 1 1 d . . . . H3AA H 0.9656 0.3806 0.1466 0.023 Uiso 1 1 calc R . . . H3AB H 0.8128 0.4405 0.1695 0.023 Uiso 1 1 calc R . . . N2A N 0.91802(19) 0.57883(9) 0.14897(8) 0.0194(3) Uani 1 1 d . . . . N2S N 0.3933(2) 0.71951(11) 0.46260(8) 0.0273(4) Uani 1 1 d . . . . C13 C 0.6323(2) 0.13830(9) 0.20657(8) 0.0137(3) Uani 1 1 d . . . . C7A C 0.6939(2) 0.73052(10) 0.26086(8) 0.0147(3) Uani 1 1 d . . . . C7 C 0.8291(2) -0.03600(10) 0.22349(8) 0.0136(3) Uani 1 1 d . . . . C15 C 0.5017(2) 0.20289(10) 0.33031(8) 0.0148(3) Uani 1 1 d . . . . C6 C 0.9457(2) -0.11179(10) 0.24972(8) 0.0138(3) Uani 1 1 d . . . . C14 C 0.6615(2) 0.09406(10) 0.27372(8) 0.0136(3) Uani 1 1 d . . . . C8A C 0.7634(2) 0.51358(10) 0.30993(8) 0.0145(3) Uani 1 1 d . . . . C14A C 0.8543(2) 0.60286(10) 0.20543(9) 0.0158(3) Uani 1 1 d . . . . C6A C 0.5714(2) 0.80566(10) 0.23905(8) 0.0152(3) Uani 1 1 d . . . . C1 C 0.9545(2) -0.11748(10) 0.31787(8) 0.0146(3) Uani 1 1 d . . . . C13A C 0.8858(2) 0.55602(10) 0.27152(8) 0.0147(3) Uani 1 1 d . . . . C12 C 0.4709(2) 0.14227(10) 0.18454(8) 0.0155(3) Uani 1 1 d . . . . H12 H 0.3861 0.1201 0.2123 0.019 Uiso 1 1 calc R . . . C11 C 0.4361(2) 0.17915(11) 0.12144(9) 0.0179(3) Uani 1 1 d . . . . H11 H 0.3286 0.1814 0.1070 0.021 Uiso 1 1 calc R . . . C8 C 0.7570(2) 0.17594(10) 0.16568(9) 0.0154(3) Uani 1 1 d . . . . C1A C 0.5516(2) 0.81377(10) 0.17176(9) 0.0168(3) Uani 1 1 d . . . . C4A C 0.3720(2) 0.93297(11) 0.25056(9) 0.0198(3) Uani 1 1 d . . . . H4A H 0.3093 0.9736 0.2769 0.024 Uiso 1 1 calc R . . . C2A C 0.4447(2) 0.88070(11) 0.14153(9) 0.0197(3) Uani 1 1 d . . . . H2A H 0.4338 0.8854 0.0961 0.024 Uiso 1 1 calc R . . . C9A C 0.8035(2) 0.47200(10) 0.37120(9) 0.0179(3) Uani 1 1 d . . . . H9A H 0.7256 0.4415 0.3962 0.022 Uiso 1 1 calc R . . . C5A C 0.4814(2) 0.86585(10) 0.27985(9) 0.0172(3) Uani 1 1 d . . . . H5A H 0.4941 0.8613 0.3252 0.021 Uiso 1 1 calc R . . . C5 C 1.0414(2) -0.17376(10) 0.21172(9) 0.0168(3) Uani 1 1 d . . . . H5 H 1.0353 -0.1711 0.1660 0.020 Uiso 1 1 calc R . . . C15A C 1.0047(2) 0.49638(10) 0.14240(8) 0.0168(3) Uani 1 1 d . . . . C12A C 1.0439(2) 0.55551(10) 0.29494(9) 0.0181(3) Uani 1 1 d . . . . H12A H 1.1263 0.5813 0.2685 0.022 Uiso 1 1 calc R . . . C18 C 0.2350(2) 0.29750(10) 0.34605(9) 0.0181(3) Uani 1 1 d . . . . H18C H 0.2915 0.3358 0.3676 0.022 Uiso 1 1 calc R . . . H18D H 0.1254 0.2941 0.3703 0.022 Uiso 1 1 calc R . . . C9 C 0.7212(2) 0.21283(11) 0.10263(9) 0.0194(3) Uani 1 1 d . . . . H9 H 0.8037 0.2377 0.0754 0.023 Uiso 1 1 calc R . . . C10 C 0.5624(2) 0.21269(11) 0.07994(9) 0.0201(3) Uani 1 1 d . . . . H10 H 0.5408 0.2351 0.0370 0.024 Uiso 1 1 calc R . . . C11A C 1.0795(2) 0.51681(11) 0.35752(9) 0.0200(3) Uani 1 1 d . . . . H11A H 1.1836 0.5187 0.3736 0.024 Uiso 1 1 calc R . . . C4 C 1.1464(2) -0.23969(10) 0.24471(9) 0.0191(3) Uani 1 1 d . . . . H4 H 1.2144 -0.2808 0.2203 0.023 Uiso 1 1 calc R . . . C2 C 1.0538(2) -0.18438(10) 0.35178(9) 0.0181(3) Uani 1 1 d . . . . H2 H 1.0552 -0.1884 0.3978 0.022 Uiso 1 1 calc R . . . C16 C 0.2456(2) 0.13718(10) 0.36509(9) 0.0178(3) Uani 1 1 d . . . . H16E H 0.3135 0.0865 0.3479 0.021 Uiso 1 1 calc R . . . H16F H 0.1396 0.1479 0.3440 0.021 Uiso 1 1 calc R . . . C10A C 0.9591(2) 0.47538(11) 0.39584(9) 0.0201(3) Uani 1 1 d . . . . H10A H 0.9819 0.4498 0.4379 0.024 Uiso 1 1 calc R . . . C3A C 0.3544(2) 0.94060(11) 0.18242(10) 0.0210(4) Uani 1 1 d . . . . H3A H 0.2810 0.9865 0.1640 0.025 Uiso 1 1 calc R . . . C18A C 1.2543(2) 0.40449(11) 0.09873(9) 0.0193(3) Uani 1 1 d . . . . H18A H 1.2308 0.3599 0.1332 0.023 Uiso 1 1 calc R . . . H18B H 1.3758 0.4053 0.0944 0.023 Uiso 1 1 calc R . . . N1S N 0.1046(3) 0.69942(13) 0.51223(12) 0.0449(5) Uani 1 1 d . . . . C3 C 1.1519(2) -0.24556(10) 0.31333(9) 0.0203(3) Uani 1 1 d . . . . H3 H 1.2220 -0.2910 0.3340 0.024 Uiso 1 1 calc R . . . C19 C 0.2094(2) 0.33354(11) 0.27487(10) 0.0235(4) Uani 1 1 d . . . . H19D H 0.1679 0.2921 0.2517 0.035 Uiso 1 1 calc GR . . . H19E H 0.3156 0.3460 0.2530 0.035 Uiso 1 1 calc GR . . . H19F H 0.1283 0.3852 0.2749 0.035 Uiso 1 1 calc GR . . . C17 C 0.2085(3) 0.12084(13) 0.43970(9) 0.0269(4) Uani 1 1 d . . . . H17D H 0.1394 0.0761 0.4488 0.040 Uiso 1 1 calc GR . . . H17E H 0.1492 0.1724 0.4573 0.040 Uiso 1 1 calc GR . . . H17F H 0.3133 0.1037 0.4601 0.040 Uiso 1 1 calc GR . . . C1S C 0.2408(3) 0.70788(13) 0.49117(10) 0.0302(4) Uani 1 1 d . . . . C16A C 1.2611(2) 0.56200(12) 0.10825(9) 0.0234(4) Uani 1 1 d D . . . H16A H 1.3655 0.5478 0.1303 0.028 Uiso 0.55 1 calc R P A 1 H16B H 1.1936 0.6111 0.1279 0.028 Uiso 0.55 1 calc R P A 1 H16C H 1.3795 0.5415 0.1150 0.028 Uiso 0.45 1 calc R P B 2 H16D H 1.2176 0.6018 0.1414 0.028 Uiso 0.45 1 calc R P B 2 C19A C 1.2002(3) 0.38298(13) 0.03327(10) 0.0285(4) Uani 1 1 d . . . . H19A H 1.2349 0.4232 -0.0019 0.043 Uiso 1 1 calc GR . . . H19B H 1.0789 0.3861 0.0362 0.043 Uiso 1 1 calc GR . . . H19C H 1.2527 0.3260 0.0243 0.043 Uiso 1 1 calc GR . . . C4S C 0.4661(3) 0.79279(13) 0.48159(11) 0.0304(4) Uani 1 1 d . . . . H4SA H 0.5639 0.8018 0.4511 0.036 Uiso 1 1 calc R . . . H4SB H 0.5049 0.7791 0.5258 0.036 Uiso 1 1 calc R . . . C3S C 0.6170(3) 0.60227(15) 0.50442(10) 0.0326(5) Uani 1 1 d . . . . H3SA H 0.6802 0.5480 0.4934 0.049 Uiso 1 1 calc GR . . . H3SB H 0.5430 0.5939 0.5439 0.049 Uiso 1 1 calc GR . . . H3SC H 0.6942 0.6402 0.5120 0.049 Uiso 1 1 calc GR . . . C5S C 0.3400(3) 0.87459(14) 0.48095(12) 0.0368(5) Uani 1 1 d . . . . H5SA H 0.3003 0.8882 0.4374 0.055 Uiso 1 1 calc GR . . . H5SB H 0.3939 0.9206 0.4922 0.055 Uiso 1 1 calc GR . . . H5SC H 0.2456 0.8670 0.5128 0.055 Uiso 1 1 calc GR . . . C2S C 0.5126(3) 0.64116(14) 0.44768(10) 0.0308(4) Uani 1 1 d . . . . H2SA H 0.5890 0.6549 0.4094 0.037 Uiso 1 1 calc R . . . H2SB H 0.4484 0.5987 0.4358 0.037 Uiso 1 1 calc R . . . C17A C 1.3030(11) 0.5852(5) 0.03469(17) 0.0371(16) Uani 0.55 1 d D P C 1 H17A H 1.3739 0.5375 0.0156 0.056 Uiso 0.55 1 calc GR P C 1 H17B H 1.3618 0.6341 0.0293 0.056 Uiso 0.55 1 calc GR P C 1 H17C H 1.1998 0.5988 0.0127 0.056 Uiso 0.55 1 calc GR P C 1 C17B C 1.2505(15) 0.6099(7) 0.0398(3) 0.049(3) Uani 0.45 1 d D P C 2 H1BA H 1.2911 0.5709 0.0065 0.074 Uiso 0.45 1 calc GR P C 2 H1BB H 1.3191 0.6549 0.0359 0.074 Uiso 0.45 1 calc GR P C 2 H1BC H 1.1346 0.6342 0.0338 0.074 Uiso 0.45 1 calc GR P C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S2A 0.00980(18) 0.01093(17) 0.0209(2) -0.00201(14) 0.00069(14) -0.00182(13) S1 0.01426(19) 0.01052(17) 0.01775(19) -0.00183(13) -0.00191(14) -0.00261(13) S2 0.00834(17) 0.01192(18) 0.0271(2) -0.00023(15) -0.00100(14) -0.00241(13) S1A 0.0213(2) 0.01125(18) 0.0184(2) -0.00275(14) 0.00118(15) -0.00202(15) O3 0.0215(6) 0.0145(5) 0.0193(6) -0.0013(4) -0.0020(5) -0.0020(5) O3A 0.0205(6) 0.0129(5) 0.0217(6) -0.0023(4) -0.0005(5) -0.0037(4) O6 0.0144(6) 0.0138(5) 0.0277(6) -0.0028(5) 0.0024(5) -0.0067(4) O6A 0.0138(6) 0.0118(5) 0.0275(6) -0.0008(5) 0.0010(5) -0.0048(4) O5A 0.0132(6) 0.0121(5) 0.0369(7) -0.0009(5) -0.0033(5) 0.0003(4) O2 0.0194(6) 0.0185(6) 0.0205(6) -0.0005(5) 0.0028(5) -0.0043(5) O1 0.0226(6) 0.0161(6) 0.0269(7) -0.0058(5) -0.0073(5) -0.0044(5) O4A 0.0154(6) 0.0323(7) 0.0230(6) -0.0073(5) 0.0003(5) -0.0030(5) O5 0.0116(6) 0.0131(6) 0.0552(9) -0.0005(6) -0.0067(6) 0.0002(5) O1A 0.0325(8) 0.0197(6) 0.0253(7) -0.0087(5) -0.0039(5) -0.0059(5) O2A 0.0306(7) 0.0160(6) 0.0250(7) 0.0006(5) 0.0089(5) -0.0031(5) O4 0.0131(6) 0.0356(7) 0.0260(7) -0.0014(6) -0.0025(5) -0.0063(5) N1 0.0133(6) 0.0086(6) 0.0176(7) -0.0007(5) -0.0014(5) -0.0008(5) N4 0.0140(7) 0.0114(6) 0.0218(7) -0.0033(5) -0.0004(5) -0.0018(5) N2 0.0104(6) 0.0113(6) 0.0241(7) -0.0017(5) -0.0015(5) -0.0012(5) N1A 0.0177(7) 0.0090(6) 0.0193(7) -0.0020(5) 0.0019(5) -0.0012(5) N4A 0.0174(7) 0.0134(6) 0.0234(7) -0.0036(5) 0.0037(5) -0.0045(5) N3 0.0136(7) 0.0109(6) 0.0314(8) -0.0038(5) 0.0015(6) -0.0016(5) N3A 0.0154(7) 0.0125(6) 0.0279(8) -0.0047(5) 0.0049(6) -0.0017(5) N2A 0.0220(8) 0.0097(6) 0.0251(8) -0.0023(5) 0.0059(6) -0.0020(5) N2S 0.0308(9) 0.0268(8) 0.0270(8) 0.0001(6) -0.0045(7) -0.0133(7) C13 0.0128(7) 0.0067(6) 0.0217(8) -0.0024(5) -0.0003(6) -0.0015(5) C7A 0.0145(7) 0.0094(7) 0.0208(8) -0.0035(6) 0.0032(6) -0.0051(6) C7 0.0118(7) 0.0093(7) 0.0200(8) -0.0016(5) 0.0015(6) -0.0040(5) C15 0.0137(7) 0.0121(7) 0.0184(8) -0.0035(6) -0.0019(6) 0.0000(6) C6 0.0114(7) 0.0082(6) 0.0222(8) -0.0003(6) -0.0014(6) -0.0030(5) C14 0.0102(7) 0.0086(7) 0.0229(8) -0.0017(6) -0.0013(6) -0.0038(5) C8A 0.0103(7) 0.0108(7) 0.0223(8) -0.0031(6) 0.0009(6) -0.0015(5) C14A 0.0136(7) 0.0086(7) 0.0253(8) -0.0013(6) 0.0020(6) -0.0045(6) C6A 0.0133(7) 0.0105(7) 0.0225(8) -0.0032(6) 0.0012(6) -0.0048(6) C1 0.0121(7) 0.0089(7) 0.0232(8) -0.0018(6) -0.0015(6) -0.0023(5) C13A 0.0127(7) 0.0085(7) 0.0227(8) -0.0032(6) 0.0015(6) -0.0011(5) C12 0.0126(7) 0.0108(7) 0.0234(8) -0.0025(6) 0.0007(6) -0.0033(6) C11 0.0117(7) 0.0168(8) 0.0252(9) -0.0024(6) -0.0034(6) -0.0012(6) C8 0.0102(7) 0.0097(7) 0.0257(8) -0.0010(6) -0.0006(6) -0.0006(5) C1A 0.0146(8) 0.0116(7) 0.0245(8) -0.0040(6) 0.0016(6) -0.0037(6) C4A 0.0156(8) 0.0129(7) 0.0322(10) -0.0086(6) 0.0030(7) -0.0043(6) C2A 0.0196(8) 0.0154(8) 0.0246(9) -0.0004(6) -0.0032(7) -0.0041(6) C9A 0.0151(8) 0.0135(7) 0.0245(9) 0.0004(6) 0.0014(6) -0.0031(6) C5A 0.0147(8) 0.0139(7) 0.0245(8) -0.0059(6) 0.0019(6) -0.0061(6) C5 0.0163(8) 0.0106(7) 0.0236(8) -0.0038(6) 0.0019(6) -0.0036(6) C15A 0.0175(8) 0.0135(7) 0.0187(8) -0.0033(6) 0.0024(6) -0.0016(6) C12A 0.0126(8) 0.0113(7) 0.0307(9) -0.0034(6) 0.0018(6) -0.0041(6) C18 0.0137(8) 0.0124(7) 0.0277(9) -0.0043(6) -0.0012(6) 0.0006(6) C9 0.0146(8) 0.0155(8) 0.0268(9) 0.0031(6) 0.0010(6) -0.0027(6) C10 0.0166(8) 0.0180(8) 0.0243(9) 0.0024(6) -0.0022(6) -0.0009(6) C11A 0.0124(8) 0.0158(8) 0.0327(10) -0.0048(7) -0.0033(7) -0.0018(6) C4 0.0138(8) 0.0099(7) 0.0338(10) -0.0053(6) 0.0008(7) -0.0021(6) C2 0.0180(8) 0.0124(7) 0.0247(9) 0.0003(6) -0.0050(6) -0.0034(6) C16 0.0167(8) 0.0137(7) 0.0244(8) -0.0040(6) -0.0006(6) -0.0059(6) C10A 0.0163(8) 0.0183(8) 0.0250(9) -0.0007(7) -0.0027(6) -0.0004(6) C3A 0.0153(8) 0.0111(7) 0.0365(10) -0.0028(7) -0.0039(7) -0.0005(6) C18A 0.0152(8) 0.0167(8) 0.0246(9) -0.0051(6) 0.0038(6) 0.0004(6) N1S 0.0336(11) 0.0355(11) 0.0626(14) 0.0191(10) -0.0033(9) -0.0113(8) C3 0.0168(8) 0.0100(7) 0.0342(10) -0.0002(6) -0.0062(7) -0.0012(6) C19 0.0266(10) 0.0146(8) 0.0313(10) -0.0040(7) -0.0114(7) -0.0026(7) C17 0.0344(11) 0.0245(9) 0.0255(9) 0.0001(7) -0.0038(8) -0.0160(8) C1S 0.0353(11) 0.0240(9) 0.0318(11) 0.0103(8) -0.0085(8) -0.0101(8) C16A 0.0196(9) 0.0205(8) 0.0314(10) -0.0025(7) 0.0020(7) -0.0093(7) C19A 0.0300(10) 0.0279(10) 0.0259(10) -0.0084(8) 0.0011(8) 0.0027(8) C4S 0.0346(11) 0.0303(10) 0.0300(10) -0.0012(8) -0.0054(8) -0.0154(9) C3S 0.0318(11) 0.0387(12) 0.0262(10) -0.0044(9) 0.0023(8) -0.0041(9) C5S 0.0393(13) 0.0320(11) 0.0425(13) -0.0096(9) 0.0000(10) -0.0139(9) C2S 0.0404(12) 0.0315(10) 0.0224(9) -0.0050(8) -0.0002(8) -0.0106(9) C17A 0.045(4) 0.032(4) 0.038(3) 0.021(2) -0.018(2) -0.023(3) C17B 0.064(7) 0.036(6) 0.055(4) 0.028(3) -0.036(3) -0.029(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O6A S2A O4A 112.88(8) O6A S2A C8A 104.85(7) O5A S2A O6A 113.23(7) O5A S2A O4A 113.10(8) O5A S2A C8A 106.49(7) O4A S2A C8A 105.38(8) O2 S1 N1 109.91(7) O2 S1 C1 111.11(7) O1 S1 O2 119.55(8) O1 S1 N1 109.65(7) O1 S1 C1 111.29(8) N1 S1 C1 91.82(7) O6 S2 C8 104.94(8) O5 S2 O6 113.18(8) O5 S2 O4 112.64(9) O5 S2 C8 107.33(8) O4 S2 O6 113.39(8) O4 S2 C8 104.44(8) O1A S1A N1A 109.48(8) O1A S1A C1A 111.36(8) O2A S1A O1A 119.61(8) O2A S1A N1A 110.03(8) O2A S1A C1A 111.11(8) N1A S1A C1A 91.70(8) C7 N1 S1 114.33(10) C14 N1 S1 119.22(11) C14 N1 C7 126.45(14) C15 N4 C18 120.07(14) C15 N4 C16 122.67(14) C18 N4 C16 117.06(13) C14 N2 C15 119.13(14) C7A N1A S1A 114.21(11) C14A N1A S1A 119.58(11) C14A N1A C7A 126.18(14) C15A N4A C18A 120.08(14) C15A N4A C16A 122.11(14) C18A N4A C16A 117.71(14) H3B N3 H3C 120.0 C15 N3 H3B 120.0 C15 N3 H3C 120.0 H3AA N3A H3AB 120.0 C15A N3A H3AA 120.0 C15A N3A H3AB 120.0 C14A N2A C15A 121.42(15) C1S N2S C4S 117.16(18) C1S N2S C2S 116.38(17) C2S N2S C4S 117.36(17) C12 C13 C14 117.11(14) C12 C13 C8 119.44(15) C8 C13 C14 123.45(14) O3A C7A N1A 125.04(15) O3A C7A C6A 126.84(15) N1A C7A C6A 108.07(14) O3 C7 N1 125.43(15) O3 C7 C6 126.70(15) N1 C7 C6 107.83(13) N4 C15 N2 118.34(14) N4 C15 N3 123.91(15) N3 C15 N2 117.50(14) C1 C6 C7 114.15(14) C1 C6 C5 120.43(15) C5 C6 C7 125.42(15) N1 C14 C13 118.13(14) N2 C14 N1 115.73(14) N2 C14 C13 126.04(14) C13A C8A S2A 121.83(13) C9A C8A S2A 119.43(12) C9A C8A C13A 118.74(15) N1A C14A C13A 117.44(14) N2A C14A N1A 116.06(15) N2A C14A C13A 126.43(15) C1A C6A C7A 114.06(14) C1A C6A C5A 120.30(16) C5A C6A C7A 125.64(16) C6 C1 S1 111.60(12) C6 C1 C2 122.77(15) C2 C1 S1 125.63(14) C8A C13A C14A 122.69(15) C12A C13A C8A 120.02(15) C12A C13A C14A 117.29(14) C13 C12 H12 119.8 C11 C12 C13 120.44(15) C11 C12 H12 119.8 C12 C11 H11 120.1 C12 C11 C10 119.87(16) C10 C11 H11 120.1 C13 C8 S2 121.14(13) C9 C8 S2 119.08(12) C9 C8 C13 119.70(15) C6A C1A S1A 111.75(12) C6A C1A C2A 122.82(16) C2A C1A S1A 125.43(14) C5A C4A H4A 119.4 C5A C4A C3A 121.25(16) C3A C4A H4A 119.4 C1A C2A H2A 121.6 C1A C2A C3A 116.80(17) C3A C2A H2A 121.6 C8A C9A H9A 119.5 C8A C9A C10A 120.91(15) C10A C9A H9A 119.5 C6A C5A H5A 121.1 C4A C5A C6A 117.75(16) C4A C5A H5A 121.1 C6 C5 H5 121.3 C4 C5 C6 117.49(16) C4 C5 H5 121.3 N4A C15A N2A 117.93(15) N3A C15A N4A 123.68(15) N3A C15A N2A 118.09(15) C13A C12A H12A 119.7 C11A C12A C13A 120.56(15) C11A C12A H12A 119.7 N4 C18 H18C 109.4 N4 C18 H18D 109.4 N4 C18 C19 111.05(14) H18C C18 H18D 108.0 C19 C18 H18C 109.4 C19 C18 H18D 109.4 C8 C9 H9 119.8 C8 C9 C10 120.31(16) C10 C9 H9 119.8 C11 C10 C9 120.10(16) C11 C10 H10 120.0 C9 C10 H10 120.0 C12A C11A H11A 120.2 C10A C11A C12A 119.69(16) C10A C11A H11A 120.2 C5 C4 H4 119.2 C5 C4 C3 121.55(16) C3 C4 H4 119.2 C1 C2 H2 121.7 C1 C2 C3 116.58(16) C3 C2 H2 121.7 N4 C16 H16E 109.3 N4 C16 H16F 109.3 N4 C16 C17 111.62(14) H16E C16 H16F 108.0 C17 C16 H16E 109.3 C17 C16 H16F 109.3 C9A C10A H10A 120.0 C11A C10A C9A 119.95(17) C11A C10A H10A 120.0 C4A C3A H3A 119.5 C2A C3A C4A 121.08(16) C2A C3A H3A 119.5 N4A C18A H18A 109.1 N4A C18A H18B 109.1 N4A C18A C19A 112.49(15) H18A C18A H18B 107.8 C19A C18A H18A 109.1 C19A C18A H18B 109.1 C4 C3 C2 121.12(16) C4 C3 H3 119.4 C2 C3 H3 119.4 C18 C19 H19D 109.5 C18 C19 H19E 109.5 C18 C19 H19F 109.5 H19D C19 H19E 109.5 H19D C19 H19F 109.5 H19E C19 H19F 109.5 C16 C17 H17D 109.5 C16 C17 H17E 109.5 C16 C17 H17F 109.5 H17D C17 H17E 109.5 H17D C17 H17F 109.5 H17E C17 H17F 109.5 N1S C1S N2S 175.8(2) N4A C16A H16A 109.4 N4A C16A H16B 109.4 N4A C16A H16C 108.7 N4A C16A H16D 108.7 N4A C16A C17A 111.3(4) N4A C16A C17B 114.2(6) H16A C16A H16B 108.0 H16C C16A H16D 107.6 C17A C16A H16A 109.4 C17A C16A H16B 109.4 C17B C16A H16C 108.7 C17B C16A H16D 108.7 C18A C19A H19A 109.5 C18A C19A H19B 109.5 C18A C19A H19C 109.5 H19A C19A H19B 109.5 H19A C19A H19C 109.5 H19B C19A H19C 109.5 N2S C4S H4SA 109.1 N2S C4S H4SB 109.1 N2S C4S C5S 112.51(18) H4SA C4S H4SB 107.8 C5S C4S H4SA 109.1 C5S C4S H4SB 109.1 H3SA C3S H3SB 109.5 H3SA C3S H3SC 109.5 H3SB C3S H3SC 109.5 C2S C3S H3SA 109.5 C2S C3S H3SB 109.5 C2S C3S H3SC 109.5 C4S C5S H5SA 109.5 C4S C5S H5SB 109.5 C4S C5S H5SC 109.5 H5SA C5S H5SB 109.5 H5SA C5S H5SC 109.5 H5SB C5S H5SC 109.5 N2S C2S C3S 114.13(17) N2S C2S H2SA 108.7 N2S C2S H2SB 108.7 C3S C2S H2SA 108.7 C3S C2S H2SB 108.7 H2SA C2S H2SB 107.6 C16A C17A H17A 109.5 C16A C17A H17B 109.5 C16A C17A H17C 109.5 H17A C17A H17B 109.5 H17A C17A H17C 109.5 H17B C17A H17C 109.5 C16A C17B H1BA 109.5 C16A C17B H1BB 109.5 C16A C17B H1BC 109.5 H1BA C17B H1BB 109.5 H1BA C17B H1BC 109.5 H1BB C17B H1BC 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S2A O6A 1.4581(12) S2A O5A 1.4491(12) S2A O4A 1.4579(13) S2A C8A 1.7878(17) S1 O2 1.4274(12) S1 O1 1.4265(12) S1 N1 1.7212(14) S1 C1 1.7497(16) S2 O6 1.4581(12) S2 O5 1.4475(13) S2 O4 1.4550(14) S2 C8 1.7846(17) S1A O1A 1.4259(14) S1A O2A 1.4253(13) S1A N1A 1.7154(15) S1A C1A 1.7507(17) O3 C7 1.196(2) O3A C7A 1.199(2) N1 C7 1.428(2) N1 C14 1.3956(19) N4 C15 1.316(2) N4 C18 1.473(2) N4 C16 1.482(2) N2 C15 1.396(2) N2 C14 1.282(2) N1A C7A 1.431(2) N1A C14A 1.394(2) N4A C15A 1.322(2) N4A C18A 1.475(2) N4A C16A 1.483(2) N3 H3B 0.8600 N3 H3C 0.8600 N3 C15 1.322(2) N3A H3AA 0.8600 N3A H3AB 0.8600 N3A C15A 1.320(2) N2A C14A 1.276(2) N2A C15A 1.390(2) N2S C1S 1.332(3) N2S C4S 1.478(3) N2S C2S 1.478(3) C13 C14 1.491(2) C13 C12 1.397(2) C13 C8 1.404(2) C7A C6A 1.477(2) C7 C6 1.486(2) C6 C1 1.385(2) C6 C5 1.393(2) C8A C13A 1.406(2) C8A C9A 1.389(2) C14A C13A 1.490(2) C6A C1A 1.381(2) C6A C5A 1.391(2) C1 C2 1.386(2) C13A C12A 1.392(2) C12 H12 0.9300 C12 C11 1.388(2) C11 H11 0.9300 C11 C10 1.389(2) C8 C9 1.389(2) C1A C2A 1.384(2) C4A H4A 0.9300 C4A C5A 1.389(2) C4A C3A 1.395(3) C2A H2A 0.9300 C2A C3A 1.390(2) C9A H9A 0.9300 C9A C10A 1.397(2) C5A H5A 0.9300 C5 H5 0.9300 C5 C4 1.391(2) C12A H12A 0.9300 C12A C11A 1.389(3) C18 H18C 0.9700 C18 H18D 0.9700 C18 C19 1.520(3) C9 H9 0.9300 C9 C10 1.393(2) C10 H10 0.9300 C11A H11A 0.9300 C11A C10A 1.386(2) C4 H4 0.9300 C4 C3 1.391(3) C2 H2 0.9300 C2 C3 1.398(2) C16 H16E 0.9700 C16 H16F 0.9700 C16 C17 1.519(3) C10A H10A 0.9300 C3A H3A 0.9300 C18A H18A 0.9700 C18A H18B 0.9700 C18A C19A 1.522(3) N1S C1S 1.155(3) C3 H3 0.9300 C19 H19D 0.9600 C19 H19E 0.9600 C19 H19F 0.9600 C17 H17D 0.9600 C17 H17E 0.9600 C17 H17F 0.9600 C16A H16A 0.9700 C16A H16B 0.9700 C16A H16C 0.9700 C16A H16D 0.9700 C16A C17A 1.5198(19) C16A C17B 1.518(2) C19A H19A 0.9600 C19A H19B 0.9600 C19A H19C 0.9600 C4S H4SA 0.9700 C4S H4SB 0.9700 C4S C5S 1.510(3) C3S H3SA 0.9600 C3S H3SB 0.9600 C3S H3SC 0.9600 C3S C2S 1.512(3) C5S H5SA 0.9600 C5S H5SB 0.9600 C5S H5SC 0.9600 C2S H2SA 0.9700 C2S H2SB 0.9700 C17A H17A 0.9600 C17A H17B 0.9600 C17A H17C 0.9600 C17B H1BA 0.9600 C17B H1BB 0.9600 C17B H1BC 0.9600 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.015 0.000 0.000 182 34 ' '