#------------------------------------------------------------------------------ #$Date: 2019-06-19 05:51:01 +0300 (Wed, 19 Jun 2019) $ #$Revision: 216095 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/85/7058504.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_7058504 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_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ02656H _journal_year 2019 _chemical_formula_moiety 'C20 H20 N4 O6 S2, 2(C6 H10 N2)' _chemical_formula_sum 'C32 H40 N8 O6 S2' _chemical_formula_weight 696.84 _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 _atom_sites_solution_primary dual _audit_creation_date 2019-05-20 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-20 deposited with the CCDC. 2019-06-18 downloaded from the CCDC. ; _cell_angle_alpha 89.298(4) _cell_angle_beta 78.292(4) _cell_angle_gamma 72.505(5) _cell_formula_units_Z 2 _cell_length_a 8.4094(5) _cell_length_b 13.2878(8) _cell_length_c 16.0580(6) _cell_measurement_reflns_used 6986 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 76.0070 _cell_measurement_theta_min 4.3470 _cell_volume 1673.47(16) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3829 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 0.00 31.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - -40.3787 38.0000 -90.0000 31 #__ type_ start__ end____ width___ exp.time_ 2 omega 64.00 115.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - 40.3787 178.0000 -150.0000 51 #__ type_ start__ end____ width___ exp.time_ 3 omega 69.00 112.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - 40.3787 178.0000 -60.0000 43 #__ type_ start__ end____ width___ exp.time_ 4 omega 104.00 175.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 112.0000 -150.0000 71 #__ type_ start__ end____ width___ exp.time_ 5 omega 133.00 177.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 112.0000 -120.0000 44 #__ type_ start__ end____ width___ exp.time_ 6 omega 144.00 177.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 -60.0000 33 #__ type_ start__ end____ width___ exp.time_ 7 omega 129.00 178.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 -90.0000 49 #__ type_ start__ end____ width___ exp.time_ 8 omega 112.00 177.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 30.0000 65 #__ type_ start__ end____ width___ exp.time_ 9 omega 98.00 124.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 89.00 129.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 45.0000 -60.0000 40 #__ type_ start__ end____ width___ exp.time_ 11 omega 83.00 177.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 30.0000 0.0000 94 #__ type_ start__ end____ width___ exp.time_ 12 omega 111.00 146.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -77.0000 -60.0000 35 #__ type_ start__ end____ width___ exp.time_ 13 omega 74.00 111.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -112.0000 30.0000 37 #__ type_ start__ end____ width___ exp.time_ 14 omega 87.00 112.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -112.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 15 omega 62.00 90.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -30.0000 -30.0000 28 #__ type_ start__ end____ width___ exp.time_ 16 omega 47.00 98.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -45.0000 -60.0000 51 #__ type_ start__ end____ width___ exp.time_ 17 omega 60.00 115.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -112.0000 -180.0000 55 #__ type_ start__ end____ width___ exp.time_ 18 omega 36.00 114.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -112.0000 -60.0000 78 #__ type_ start__ end____ width___ exp.time_ 19 omega 69.00 129.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - 40.3787 -178.0000 30.0000 60 #__ type_ start__ end____ width___ exp.time_ 20 omega 66.00 117.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - 40.3787 -178.0000 120.0000 51 #__ type_ start__ end____ width___ exp.time_ 21 omega 34.00 91.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -77.0000 -60.0000 57 #__ type_ start__ end____ width___ exp.time_ 22 omega 32.00 76.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -95.0000 -120.0000 44 #__ type_ start__ end____ width___ exp.time_ 23 omega 29.00 107.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -95.0000 -150.0000 78 #__ type_ start__ end____ width___ exp.time_ 24 omega 43.00 90.00 1.0000 6.7550 omega____ theta____ kappa____ phi______ frames - 113.0000 -30.0000 90.0000 47 #__ type_ start__ end____ width___ exp.time_ 25 omega -129.00 33.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - -40.3787 0.0000 -90.0000 162 #__ type_ start__ end____ width___ exp.time_ 26 omega 3.00 28.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - 40.0000 88.0000 94.7449 25 #__ type_ start__ end____ width___ exp.time_ 27 omega 3.00 28.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - 40.0000 87.0000 -138.0388 25 #__ type_ start__ end____ width___ exp.time_ 28 omega -110.00 -41.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - -40.3787 -57.0000 -150.0000 69 #__ type_ start__ end____ width___ exp.time_ 29 omega -39.00 -12.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - -40.3787 -57.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 30 omega -76.00 -26.00 1.0000 1.6900 omega____ theta____ kappa____ phi______ frames - -40.3787 19.0000 30.0000 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0213415000 _diffrn_orient_matrix_UB_12 0.1090567000 _diffrn_orient_matrix_UB_13 0.0150665000 _diffrn_orient_matrix_UB_21 -0.1756766000 _diffrn_orient_matrix_UB_22 0.0540564000 _diffrn_orient_matrix_UB_23 -0.0211525000 _diffrn_orient_matrix_UB_31 -0.0852241000 _diffrn_orient_matrix_UB_32 0.0013062000 _diffrn_orient_matrix_UB_33 0.0946102000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_unetI/netI 0.0521 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 14698 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.162 _diffrn_reflns_theta_min 3.492 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.918 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72705 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.383 _exptl_crystal_description prism _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.540 _refine_diff_density_min -0.766 _refine_diff_density_rms 0.069 _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 451 _refine_ls_number_reflns 6847 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0455 _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^)+(0.0729P)^2^+0.4039P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1170 _refine_ls_wR_factor_ref 0.1259 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5734 _reflns_number_total 6847 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj02656h2.cif _cod_data_source_block 0dv-23-11-3 _cod_database_code 7058504 _shelx_shelxl_version_number 2014/7 _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 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 72.42 _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 2. Restrained distances C11A-C10S = C11S-C10S = C9A-C10S = C9S-C10S 1.53 with sigma of 0.02 N4S-C8A = N4S-C8S = N4S-C12S = N4S-C12A 1.47 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C12S) = Uanis(C12A) = Uanis(C8A) = Uanis(C8S) 4. Others Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) H10D(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5) C12S(0.5) H12A(0.5) H12B(0.5) C11A(0.5) H11A(0.5) H11B(0.5) C8S(0.5) H8SA(0.5) H8SB(0.5) C9S(0.5) H9SA(0.5) H9SB(0.5) C11S(0.5) H11C(0.5) H11D(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) C12A(0.5) H12C(0.5) H12D(0.5) 5.a Secondary CH2 refined with riding coordinates: C16(H16A,H16B), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C20(H20A,H20B), C5S(H5SA, H5SB), C6S(H6SA,H6SB), C18(H18A,H18B), C17(H17A,H17B), C4S(H4SA,H4SB), C19(H19A,H19B), C10S(H10A,H10B), C10S(H10C,H10D), C9A(H9AA,H9AB), C12S(H12A, H12B), C11A(H11A,H11B), C8S(H8SA,H8SB), C9S(H9SA,H9SB), C11S(H11C,H11D), C8A(H8AA,H8AB), C12A(H12C,H12D) 5.b Aromatic/amide H refined with riding coordinates: C9(H9), C10(H10), C11(H11), C2(H2), C12(H12), C5(H5), C4(H4), C3(H3) 5.c X=CH2 refined with riding coordinates: N3(H3A,H3B) ; _shelx_res_file ; 0dv-23-11-3.res created by SHELXL-2014/7 TITL 0dv-23-11-3_a.res in P-1 REM Old TITL DV-23-11-3 in P-1 REM SHELXT solution in P-1 REM R1 0.119, Rweak 0.006, Alpha 0.047, Orientation as input REM Formula found by SHELXT: C33 N6 O7 S2 CELL 1.54184 8.4094 13.2878 16.058 89.298 78.292 72.505 ZERR 2 0.0005 0.0008 0.0006 0.004 0.004 0.005 LATT 1 SFAC C H N O S UNIT 64 80 16 12 4 DFIX 1.53 C11A C10S C11S C10S C9A C10S C9S C10S DFIX 1.47 N4S C8A N4S C8S N4S C12S N4S C12A EADP C12S C12A C8A C8S L.S. 100 PLAN 20 BOND $H list 4 fmap 2 acta OMIT 10 8 0 OMIT -5 4 13 OMIT -9 -9 3 OMIT -2 13 7 OMIT 10 8 1 OMIT -1 1 5 OMIT 10 9 2 OMIT -9 -11 2 OMIT -9 -10 3 OMIT -2 12 8 OMIT 0 2 19 REM REM REM WGHT 0.072900 0.403900 FVAR 0.62981 S2 5 0.640823 0.626765 0.822786 11.00000 0.01203 0.01216 = 0.01165 -0.00012 -0.00052 -0.00600 S1 5 0.675683 0.346405 0.623441 11.00000 0.01536 0.01051 = 0.00986 -0.00314 -0.00025 -0.00316 O1 4 0.793954 0.303777 0.676424 11.00000 0.01840 0.01662 = 0.01578 -0.00083 -0.00302 -0.00158 O4 4 0.642463 0.556353 0.894845 11.00000 0.01771 0.01780 = 0.01241 0.00429 -0.00279 -0.00993 O2 4 0.571626 0.286518 0.603517 11.00000 0.02428 0.01667 = 0.01588 -0.00388 -0.00127 -0.00910 O5 4 0.742333 0.570067 0.744145 11.00000 0.01505 0.02736 = 0.01215 -0.00222 0.00198 -0.00282 O6 4 0.676036 0.722084 0.843577 11.00000 0.02099 0.01549 = 0.03634 0.00216 -0.00954 -0.01006 O3 4 0.476576 0.642848 0.615770 11.00000 0.02977 0.01294 = 0.01568 0.00033 0.00012 0.00040 N2 3 0.450487 0.398938 0.781356 11.00000 0.01708 0.01118 = 0.01228 -0.00154 0.00007 -0.00525 N3 3 0.421479 0.434434 0.926529 11.00000 0.01863 0.01934 = 0.01101 0.00105 -0.00105 -0.01292 AFIX 93 H3A 2 0.381558 0.426125 0.978983 11.00000 -1.20000 H3B 2 0.494654 0.468516 0.913883 11.00000 -1.20000 AFIX 0 N1 3 0.546796 0.471061 0.661912 11.00000 0.01837 0.01128 = 0.00893 -0.00148 0.00029 -0.00403 N4 3 0.259056 0.341658 0.878759 11.00000 0.01857 0.01708 = 0.01385 0.00090 -0.00438 -0.01000 N2S 3 0.755290 1.011305 0.943672 11.00000 0.02262 0.01153 = 0.01890 0.00064 -0.00442 -0.00820 C15 1 0.370584 0.394987 0.865606 11.00000 0.01483 0.00969 = 0.01106 -0.00192 -0.00002 -0.00240 N1S 3 0.831714 0.949967 1.081576 11.00000 0.03817 0.02029 = 0.02843 0.00275 -0.01269 -0.00977 C8 1 0.424177 0.665366 0.811343 11.00000 0.01451 0.01279 = 0.01034 -0.00191 -0.00024 -0.00509 C9 1 0.321238 0.767949 0.838294 11.00000 0.02003 0.01192 = 0.01554 -0.00513 -0.00147 -0.00551 AFIX 43 H9 2 0.367577 0.815156 0.859322 11.00000 -1.20000 AFIX 0 C14 1 0.452900 0.484644 0.744875 11.00000 0.01337 0.01107 = 0.01202 -0.00209 -0.00238 -0.00533 C13 1 0.353133 0.594831 0.779731 11.00000 0.01603 0.00926 = 0.00824 -0.00123 0.00000 -0.00357 C6 1 0.703052 0.504335 0.530652 11.00000 0.01949 0.01644 = 0.00918 -0.00300 -0.00118 -0.00537 C7 1 0.564862 0.552073 0.604398 11.00000 0.01912 0.01504 = 0.00929 -0.00033 -0.00173 -0.00510 C1 1 0.773701 0.396051 0.532500 11.00000 0.01814 0.01719 = 0.01013 -0.00196 -0.00244 -0.00626 C10 1 0.150218 0.800037 0.833947 11.00000 0.01871 0.01299 = 0.02003 -0.00484 -0.00058 -0.00125 AFIX 43 H10 2 0.083420 0.869148 0.850528 11.00000 -1.20000 AFIX 0 C11 1 0.078164 0.729129 0.804839 11.00000 0.01404 0.01798 = 0.01873 -0.00204 -0.00184 -0.00252 AFIX 43 H11 2 -0.037050 0.750150 0.803200 11.00000 -1.20000 AFIX 0 C2 1 0.910906 0.337640 0.471420 11.00000 0.01842 0.01852 = 0.01433 -0.00434 0.00073 -0.00596 AFIX 43 H2 2 0.956389 0.264896 0.473818 11.00000 -1.20000 AFIX 0 C12 1 0.179834 0.626856 0.778313 11.00000 0.01707 0.01496 = 0.01507 -0.00297 -0.00355 -0.00720 AFIX 43 H12 2 0.131873 0.579159 0.759386 11.00000 -1.20000 AFIX 0 C5 1 0.768912 0.559705 0.464800 11.00000 0.02257 0.02056 = 0.01191 0.00169 -0.00218 -0.00759 AFIX 43 H5 2 0.721760 0.632292 0.462244 11.00000 -1.20000 AFIX 0 C4 1 0.907917 0.502094 0.403081 11.00000 0.02326 0.02924 = 0.01083 0.00092 -0.00071 -0.01264 AFIX 43 H4 2 0.955040 0.537168 0.358976 11.00000 -1.20000 AFIX 0 C3 1 0.977853 0.392976 0.406051 11.00000 0.01778 0.02754 = 0.01122 -0.00498 0.00230 -0.00745 AFIX 43 H3 2 1.070339 0.356607 0.363903 11.00000 -1.20000 AFIX 0 C16 1 0.206764 0.297199 0.808704 11.00000 0.02217 0.01767 = 0.01688 -0.00477 -0.00579 -0.00929 AFIX 23 H16A 2 0.236041 0.221015 0.811478 11.00000 -1.20000 H16B 2 0.266824 0.313042 0.754384 11.00000 -1.20000 AFIX 0 C2S 1 0.696042 1.126451 0.934141 11.00000 0.02705 0.01096 = 0.02179 -0.00129 -0.00319 -0.00810 AFIX 23 H2SA 2 0.756885 1.161123 0.963481 11.00000 -1.20000 H2SB 2 0.575251 1.154402 0.958929 11.00000 -1.20000 AFIX 0 C1S 1 0.793943 0.979111 1.018142 11.00000 0.02189 0.01343 = 0.02403 -0.00178 -0.00303 -0.00738 C3S 1 0.728615 1.147308 0.839779 11.00000 0.02430 0.01410 = 0.02103 0.00201 -0.00366 -0.00822 AFIX 23 H3SA 2 0.850436 1.125380 0.816684 11.00000 -1.20000 H3SB 2 0.684036 1.222448 0.832511 11.00000 -1.20000 AFIX 0 C20 1 0.171689 0.322846 0.964261 11.00000 0.02276 0.02306 = 0.01481 0.00478 -0.00311 -0.01619 AFIX 23 H20A 2 0.207524 0.356417 1.007323 11.00000 -1.20000 H20B 2 0.202541 0.247576 0.972693 11.00000 -1.20000 AFIX 0 C5S 1 0.707165 0.969030 0.804690 11.00000 0.02577 0.01742 = 0.02164 -0.00288 -0.00559 -0.00758 AFIX 23 H5SA 2 0.647356 0.932578 0.776271 11.00000 -1.20000 H5SB 2 0.827897 0.941607 0.779623 11.00000 -1.20000 AFIX 0 C6S 1 0.677534 0.948093 0.899041 11.00000 0.02307 0.01550 = 0.02311 -0.00124 -0.00379 -0.01068 AFIX 23 H6SA 2 0.556139 0.966911 0.922776 11.00000 -1.20000 H6SB 2 0.727888 0.873564 0.906651 11.00000 -1.20000 AFIX 0 C18 1 -0.078960 0.322757 0.902233 11.00000 0.01650 0.01640 = 0.03729 -0.00149 -0.00704 -0.00724 AFIX 23 H18A 2 -0.200628 0.355027 0.907228 11.00000 -1.20000 H18B 2 -0.057232 0.247211 0.907133 11.00000 -1.20000 AFIX 0 C17 1 0.015782 0.344158 0.815832 11.00000 0.02371 0.01783 = 0.02433 -0.00196 -0.01071 -0.00633 AFIX 23 H17A 2 -0.018972 0.313146 0.770908 11.00000 -1.20000 H17B 2 -0.012433 0.419744 0.809171 11.00000 -1.20000 AFIX 0 C4S 1 0.644083 1.087490 0.791327 11.00000 0.02425 0.01770 = 0.02299 0.00115 -0.00816 -0.00495 AFIX 23 H4SA 2 0.670263 1.099535 0.731083 11.00000 -1.20000 H4SB 2 0.521342 1.113552 0.811101 11.00000 -1.20000 AFIX 0 C19 1 -0.021009 0.367468 0.973486 11.00000 0.02309 0.02303 = 0.02275 -0.00159 0.00064 -0.01301 AFIX 23 H19A 2 -0.077497 0.349882 1.028055 11.00000 -1.20000 H19B 2 -0.053019 0.443843 0.971920 11.00000 -1.20000 AFIX 0 N3S 3 0.740736 0.853149 0.597574 11.00000 0.04440 0.06213 = 0.04106 -0.00227 0.00294 0.01702 C7S 1 0.597553 0.893168 0.602410 11.00000 0.03958 0.04173 = 0.02701 -0.00223 0.00000 0.00805 C10S 1 0.075214 1.043550 0.620061 11.00000 0.03476 0.04420 = 0.04744 -0.00373 -0.01070 -0.00573 PART 1 AFIX 23 H10A 2 0.068480 1.083893 0.569448 10.50000 -1.20000 H10B 2 -0.039592 1.054426 0.652758 10.50000 -1.20000 AFIX 23 PART 0 PART 2 H10C 2 0.029002 1.020110 0.674518 10.50000 -1.20000 H10D 2 -0.019744 1.089432 0.598666 10.50000 -1.20000 AFIX 0 PART 0 PART 1 C9A 1 0.178898 1.079021 0.672325 10.50000 0.03851 0.05979 = 0.04042 -0.02832 -0.00801 0.00901 AFIX 23 H9AA 2 0.164695 1.047876 0.727230 10.50000 -1.20000 H9AB 2 0.132187 1.155058 0.682406 10.50000 -1.20000 AFIX 0 PART 0 PART 2 C12S 1 0.311454 0.882282 0.590576 10.50000 0.03967 0.02414 = 0.04614 -0.00914 -0.01167 -0.00044 AFIX 23 H12A 2 0.273483 0.849808 0.642154 10.50000 -1.20000 H12B 2 0.373374 0.826103 0.547433 10.50000 -1.20000 AFIX 0 PART 0 PART 1 C11A 1 0.164474 0.922603 0.594294 10.50000 0.06023 0.04321 = 0.06317 0.01548 -0.02483 -0.03073 AFIX 23 H11A 2 0.146689 0.882647 0.644433 10.50000 -1.20000 H11B 2 0.108612 0.901815 0.553192 10.50000 -1.20000 AFIX 0 PART 0 PART 2 C8S 1 0.344891 1.033980 0.662319 10.50000 0.03967 0.02414 = 0.04614 -0.00914 -0.01167 -0.00044 AFIX 23 H8SA 2 0.425291 1.072521 0.664852 10.50000 -1.20000 H8SB 2 0.308767 1.013147 0.719418 10.50000 -1.20000 AFIX 0 C9S 1 0.190555 1.107641 0.634450 10.50000 0.03291 0.02988 = 0.03612 -0.01864 -0.00643 -0.00139 AFIX 23 H9SA 2 0.226415 1.139722 0.582264 10.50000 -1.20000 H9SB 2 0.129660 1.163477 0.678010 10.50000 -1.20000 AFIX 0 C11S 1 0.157365 0.951470 0.561132 10.50000 0.03724 0.02087 = 0.04729 -0.00512 -0.01199 -0.00942 AFIX 23 H11C 2 0.191613 0.973932 0.504385 10.50000 -1.20000 H11D 2 0.077999 0.912064 0.558953 10.50000 -1.20000 AFIX 0 PART 0 PART 1 C8A 1 0.367822 1.052843 0.635353 10.50000 0.03967 0.02414 = 0.04614 -0.00914 -0.01167 -0.00044 AFIX 23 H8AA 2 0.387442 1.095625 0.587252 10.50000 -1.20000 H8AB 2 0.426516 1.066845 0.677927 10.50000 -1.20000 AFIX 0 C12A 1 0.354001 0.891855 0.556792 10.50000 0.03967 0.02414 = 0.04614 -0.00914 -0.01167 -0.00044 AFIX 23 H12C 2 0.403187 0.815674 0.555099 10.50000 -1.20000 H12D 2 0.373336 0.914893 0.499077 10.50000 -1.20000 AFIX 0 PART 0 N4S 3 0.431128 0.940187 0.607912 11.00000 0.03099 0.03597 = 0.03882 -0.01519 -0.00016 0.00160 HKLF 4 REM 0dv-23-11-3_a.res in P-1 REM R1 = 0.0455 for 5734 Fo > 4sig(Fo) and 0.0559 for all 6847 data REM 451 parameters refined using 8 restraints END WGHT 0.0729 0.4077 REM Highest difference peak 0.540, deepest hole -0.766, 1-sigma level 0.069 Q1 1 0.5247 0.6520 0.8139 11.00000 0.05 0.54 Q2 1 0.6446 0.2891 0.6159 11.00000 0.05 0.41 Q3 1 0.5922 0.2947 0.6477 11.00000 0.05 0.39 Q4 1 0.3975 0.6374 0.7835 11.00000 0.05 0.38 Q5 1 0.5790 0.5578 0.8554 11.00000 0.05 0.37 Q6 1 0.6980 0.6801 0.8083 11.00000 0.05 0.36 Q7 1 0.3513 0.8976 0.6190 11.00000 0.05 0.35 Q8 1 -0.0461 0.3525 0.9320 11.00000 0.05 0.34 Q9 1 0.5613 0.3760 0.5894 11.00000 0.05 0.31 Q10 1 0.7199 0.3370 0.6697 11.00000 0.05 0.31 Q11 1 0.2421 0.3272 0.8384 11.00000 0.05 0.31 Q12 1 0.6109 0.5913 0.7727 11.00000 0.05 0.31 Q13 1 0.7815 0.3037 0.6378 11.00000 0.05 0.30 Q14 1 0.7200 0.9787 0.9174 11.00000 0.05 0.30 Q15 1 0.7601 0.3966 0.5895 11.00000 0.05 0.30 Q16 1 0.6233 0.7264 0.7990 11.00000 0.05 0.30 Q17 1 0.2763 0.6169 0.7642 11.00000 0.05 0.29 Q18 1 0.2366 0.7879 0.8221 11.00000 0.05 0.29 Q19 1 0.6878 0.6209 0.8783 11.00000 0.05 0.29 Q20 1 0.1461 1.0764 0.6301 11.00000 0.05 0.27 ; _shelx_res_checksum 97442 _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 S2 S 0.64082(5) 0.62677(3) 0.82279(3) 0.01171(11) Uani 1 1 d . . . . S1 S 0.67568(6) 0.34640(3) 0.62344(3) 0.01241(11) Uani 1 1 d . . . . O1 O 0.79395(18) 0.30378(10) 0.67642(9) 0.0178(3) Uani 1 1 d . . . . O4 O 0.64246(17) 0.55635(10) 0.89485(8) 0.0150(3) Uani 1 1 d . . . . O2 O 0.57163(19) 0.28652(10) 0.60352(9) 0.0187(3) Uani 1 1 d . . . . O5 O 0.74233(18) 0.57007(11) 0.74415(9) 0.0197(3) Uani 1 1 d . . . . O6 O 0.67604(19) 0.72208(11) 0.84358(10) 0.0227(3) Uani 1 1 d . . . . O3 O 0.4766(2) 0.64285(10) 0.61577(9) 0.0217(3) Uani 1 1 d . . . . N2 N 0.4505(2) 0.39894(12) 0.78136(10) 0.0137(3) Uani 1 1 d . . . . N3 N 0.4215(2) 0.43443(12) 0.92653(10) 0.0150(3) Uani 1 1 d . . . . H3A H 0.3816 0.4261 0.9790 0.018 Uiso 1 1 calc R . . . H3B H 0.4947 0.4685 0.9139 0.018 Uiso 1 1 calc R . . . N1 N 0.5468(2) 0.47106(11) 0.66191(10) 0.0134(3) Uani 1 1 d . . . . N4 N 0.2591(2) 0.34166(12) 0.87876(10) 0.0153(3) Uani 1 1 d . . . . N2S N 0.7553(2) 1.01131(12) 0.94367(11) 0.0170(3) Uani 1 1 d . . . . C15 C 0.3706(2) 0.39499(13) 0.86561(11) 0.0125(3) Uani 1 1 d . . . . N1S N 0.8317(3) 0.94997(14) 1.08158(13) 0.0279(4) Uani 1 1 d . . . . C8 C 0.4242(2) 0.66537(14) 0.81134(11) 0.0127(3) Uani 1 1 d . . . . C9 C 0.3212(3) 0.76795(14) 0.83829(12) 0.0160(4) Uani 1 1 d . . . . H9 H 0.3676 0.8152 0.8593 0.019 Uiso 1 1 calc R . . . C14 C 0.4529(2) 0.48464(13) 0.74487(11) 0.0118(3) Uani 1 1 d . . . . C13 C 0.3531(2) 0.59483(13) 0.77973(11) 0.0116(3) Uani 1 1 d . . . . C6 C 0.7031(3) 0.50433(14) 0.53065(11) 0.0153(4) Uani 1 1 d . . . . C7 C 0.5649(2) 0.55207(14) 0.60440(11) 0.0147(4) Uani 1 1 d . . . . C1 C 0.7737(2) 0.39605(15) 0.53250(12) 0.0150(4) Uani 1 1 d . . . . C10 C 0.1502(3) 0.80004(14) 0.83395(13) 0.0185(4) Uani 1 1 d . . . . H10 H 0.0834 0.8691 0.8505 0.022 Uiso 1 1 calc R . . . C11 C 0.0782(3) 0.72913(15) 0.80484(12) 0.0177(4) Uani 1 1 d . . . . H11 H -0.0370 0.7502 0.8032 0.021 Uiso 1 1 calc R . . . C2 C 0.9109(3) 0.33764(15) 0.47142(12) 0.0176(4) Uani 1 1 d . . . . H2 H 0.9564 0.2649 0.4738 0.021 Uiso 1 1 calc R . . . C12 C 0.1798(2) 0.62686(14) 0.77831(12) 0.0151(4) Uani 1 1 d . . . . H12 H 0.1319 0.5792 0.7594 0.018 Uiso 1 1 calc R . . . C5 C 0.7689(3) 0.55971(15) 0.46480(12) 0.0183(4) Uani 1 1 d . . . . H5 H 0.7218 0.6323 0.4622 0.022 Uiso 1 1 calc R . . . C4 C 0.9079(3) 0.50209(17) 0.40308(12) 0.0205(4) Uani 1 1 d . . . . H4 H 0.9550 0.5372 0.3590 0.025 Uiso 1 1 calc R . . . C3 C 0.9779(3) 0.39298(16) 0.40605(12) 0.0195(4) Uani 1 1 d . . . . H3 H 1.0703 0.3566 0.3639 0.023 Uiso 1 1 calc R . . . C16 C 0.2068(3) 0.29720(15) 0.80870(12) 0.0179(4) Uani 1 1 d . . . . H16A H 0.2360 0.2210 0.8115 0.021 Uiso 1 1 calc R . . . H16B H 0.2668 0.3130 0.7544 0.021 Uiso 1 1 calc R . . . C2S C 0.6960(3) 1.12645(14) 0.93414(13) 0.0197(4) Uani 1 1 d . . . . H2SA H 0.7569 1.1611 0.9635 0.024 Uiso 1 1 calc R . . . H2SB H 0.5753 1.1544 0.9589 0.024 Uiso 1 1 calc R . . . C1S C 0.7939(3) 0.97911(14) 1.01814(14) 0.0196(4) Uani 1 1 d . . . . C3S C 0.7286(3) 1.14731(14) 0.83978(13) 0.0194(4) Uani 1 1 d . . . . H3SA H 0.8504 1.1254 0.8167 0.023 Uiso 1 1 calc R . . . H3SB H 0.6840 1.2224 0.8325 0.023 Uiso 1 1 calc R . . . C20 C 0.1717(3) 0.32285(15) 0.96426(12) 0.0183(4) Uani 1 1 d . . . . H20A H 0.2075 0.3564 1.0073 0.022 Uiso 1 1 calc R . . . H20B H 0.2025 0.2476 0.9727 0.022 Uiso 1 1 calc R . . . C5S C 0.7072(3) 0.96903(15) 0.80469(13) 0.0213(4) Uani 1 1 d . . . . H5SA H 0.6474 0.9326 0.7763 0.026 Uiso 1 1 calc R . . . H5SB H 0.8279 0.9416 0.7796 0.026 Uiso 1 1 calc R . . . C6S C 0.6775(3) 0.94809(15) 0.89904(13) 0.0196(4) Uani 1 1 d . . . . H6SA H 0.5561 0.9669 0.9228 0.024 Uiso 1 1 calc R . . . H6SB H 0.7279 0.8736 0.9067 0.024 Uiso 1 1 calc R . . . C18 C -0.0790(3) 0.32276(15) 0.90223(15) 0.0227(4) Uani 1 1 d . . . . H18A H -0.2006 0.3550 0.9072 0.027 Uiso 1 1 calc R . . . H18B H -0.0572 0.2472 0.9071 0.027 Uiso 1 1 calc R . . . C17 C 0.0158(3) 0.34416(15) 0.81583(14) 0.0211(4) Uani 1 1 d . . . . H17A H -0.0190 0.3131 0.7709 0.025 Uiso 1 1 calc R . . . H17B H -0.0124 0.4197 0.8092 0.025 Uiso 1 1 calc R . . . C4S C 0.6441(3) 1.08749(15) 0.79133(14) 0.0215(4) Uani 1 1 d . . . . H4SA H 0.6703 1.0995 0.7311 0.026 Uiso 1 1 calc R . . . H4SB H 0.5213 1.1136 0.8111 0.026 Uiso 1 1 calc R . . . C19 C -0.0210(3) 0.36747(16) 0.97349(14) 0.0224(4) Uani 1 1 d . . . . H19A H -0.0775 0.3499 1.0281 0.027 Uiso 1 1 calc R . . . H19B H -0.0530 0.4438 0.9719 0.027 Uiso 1 1 calc R . . . N3S N 0.7407(4) 0.8531(2) 0.59757(17) 0.0584(8) Uani 1 1 d . . . . C7S C 0.5976(4) 0.8932(2) 0.60241(17) 0.0417(7) Uani 1 1 d . . . . C10S C 0.0752(4) 1.0435(2) 0.6201(2) 0.0432(6) Uani 1 1 d D . . . H10A H 0.0685 1.0839 0.5694 0.052 Uiso 0.5 1 calc R P A 1 H10B H -0.0396 1.0544 0.6528 0.052 Uiso 0.5 1 calc R P A 1 H10C H 0.0290 1.0201 0.6745 0.052 Uiso 0.5 1 calc R P B 2 H10D H -0.0197 1.0894 0.5987 0.052 Uiso 0.5 1 calc R P B 2 C9A C 0.1789(10) 1.0790(7) 0.6723(5) 0.051(2) Uani 0.5 1 d D P C 1 H9AA H 0.1647 1.0479 0.7272 0.062 Uiso 0.5 1 calc R P C 1 H9AB H 0.1322 1.1551 0.6824 0.062 Uiso 0.5 1 calc R P C 1 C12S C 0.3115(9) 0.8823(5) 0.5906(4) 0.0382(11) Uani 0.5 1 d D P C 2 H12A H 0.2735 0.8498 0.6422 0.046 Uiso 0.5 1 calc R P C 2 H12B H 0.3734 0.8261 0.5474 0.046 Uiso 0.5 1 calc R P C 2 C11A C 0.1645(11) 0.9226(6) 0.5943(6) 0.050(2) Uani 0.5 1 d D P C 1 H11A H 0.1467 0.8826 0.6444 0.061 Uiso 0.5 1 calc R P C 1 H11B H 0.1086 0.9018 0.5532 0.061 Uiso 0.5 1 calc R P C 1 C8S C 0.3449(11) 1.0340(5) 0.6623(5) 0.0382(11) Uani 0.5 1 d D P C 2 H8SA H 0.4253 1.0725 0.6649 0.046 Uiso 0.5 1 calc R P C 2 H8SB H 0.3088 1.0131 0.7194 0.046 Uiso 0.5 1 calc R P C 2 C9S C 0.1906(9) 1.1076(5) 0.6344(4) 0.0347(13) Uani 0.5 1 d D P C 2 H9SA H 0.2264 1.1397 0.5823 0.042 Uiso 0.5 1 calc R P C 2 H9SB H 0.1297 1.1635 0.6780 0.042 Uiso 0.5 1 calc R P C 2 C11S C 0.1574(8) 0.9515(5) 0.5611(5) 0.0345(13) Uani 0.5 1 d D P C 2 H11C H 0.1916 0.9739 0.5044 0.041 Uiso 0.5 1 calc R P C 2 H11D H 0.0780 0.9121 0.5590 0.041 Uiso 0.5 1 calc R P C 2 C8A C 0.3678(11) 1.0528(5) 0.6354(5) 0.0382(11) Uani 0.5 1 d D P C 1 H8AA H 0.3874 1.0956 0.5873 0.046 Uiso 0.5 1 calc R P C 1 H8AB H 0.4265 1.0668 0.6779 0.046 Uiso 0.5 1 calc R P C 1 C12A C 0.3540(9) 0.8919(5) 0.5568(4) 0.0382(11) Uani 0.5 1 d D P C 1 H12C H 0.4032 0.8157 0.5551 0.046 Uiso 0.5 1 calc R P C 1 H12D H 0.3733 0.9149 0.4991 0.046 Uiso 0.5 1 calc R P C 1 N4S N 0.4311(3) 0.94019(18) 0.60791(15) 0.0388(5) Uani 1 1 d D . . . 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 S2 0.0120(2) 0.01216(19) 0.0117(2) -0.00012(15) -0.00052(16) -0.00600(15) S1 0.0154(2) 0.01051(19) 0.0099(2) -0.00314(14) -0.00025(16) -0.00316(15) O1 0.0184(7) 0.0166(6) 0.0158(6) -0.0008(5) -0.0030(5) -0.0016(5) O4 0.0177(7) 0.0178(6) 0.0124(6) 0.0043(5) -0.0028(5) -0.0099(5) O2 0.0243(8) 0.0167(6) 0.0159(6) -0.0039(5) -0.0013(6) -0.0091(5) O5 0.0151(7) 0.0274(7) 0.0122(6) -0.0022(5) 0.0020(5) -0.0028(5) O6 0.0210(8) 0.0155(6) 0.0363(9) 0.0022(6) -0.0095(6) -0.0101(5) O3 0.0298(8) 0.0129(6) 0.0157(7) 0.0003(5) 0.0001(6) 0.0004(5) N2 0.0171(8) 0.0112(6) 0.0123(7) -0.0015(5) 0.0001(6) -0.0053(6) N3 0.0186(8) 0.0193(7) 0.0110(7) 0.0010(6) -0.0010(6) -0.0129(6) N1 0.0184(8) 0.0113(6) 0.0089(7) -0.0015(5) 0.0003(6) -0.0040(6) N4 0.0186(8) 0.0171(7) 0.0139(8) 0.0009(6) -0.0044(6) -0.0100(6) N2S 0.0226(9) 0.0115(7) 0.0189(8) 0.0006(6) -0.0044(7) -0.0082(6) C15 0.0148(9) 0.0097(7) 0.0111(8) -0.0019(6) 0.0000(7) -0.0024(6) N1S 0.0382(11) 0.0203(8) 0.0284(10) 0.0028(7) -0.0127(9) -0.0098(8) C8 0.0145(9) 0.0128(8) 0.0103(8) -0.0019(6) -0.0002(7) -0.0051(7) C9 0.0200(10) 0.0119(8) 0.0155(9) -0.0051(6) -0.0015(7) -0.0055(7) C14 0.0134(9) 0.0111(7) 0.0120(8) -0.0021(6) -0.0024(7) -0.0053(6) C13 0.0160(9) 0.0093(7) 0.0082(8) -0.0012(6) 0.0000(7) -0.0036(6) C6 0.0195(10) 0.0164(8) 0.0092(8) -0.0030(6) -0.0012(7) -0.0054(7) C7 0.0191(10) 0.0150(8) 0.0093(8) -0.0003(6) -0.0017(7) -0.0051(7) C1 0.0181(9) 0.0172(8) 0.0101(8) -0.0020(6) -0.0024(7) -0.0063(7) C10 0.0187(10) 0.0130(8) 0.0200(9) -0.0048(7) -0.0006(8) -0.0013(7) C11 0.0140(9) 0.0180(8) 0.0187(9) -0.0020(7) -0.0018(7) -0.0025(7) C2 0.0184(10) 0.0185(8) 0.0143(9) -0.0043(7) 0.0007(7) -0.0060(7) C12 0.0171(9) 0.0150(8) 0.0151(9) -0.0030(6) -0.0036(7) -0.0072(7) C5 0.0226(10) 0.0206(9) 0.0119(9) 0.0017(7) -0.0022(8) -0.0076(7) C4 0.0233(11) 0.0292(10) 0.0108(9) 0.0009(7) -0.0007(8) -0.0126(8) C3 0.0178(10) 0.0275(10) 0.0112(8) -0.0050(7) 0.0023(7) -0.0074(8) C16 0.0222(10) 0.0177(8) 0.0169(9) -0.0048(7) -0.0058(8) -0.0093(7) C2S 0.0270(11) 0.0110(8) 0.0218(10) -0.0013(7) -0.0032(8) -0.0081(7) C1S 0.0219(10) 0.0134(8) 0.0240(10) -0.0018(7) -0.0030(8) -0.0074(7) C3S 0.0243(10) 0.0141(8) 0.0210(10) 0.0020(7) -0.0037(8) -0.0082(7) C20 0.0228(10) 0.0231(9) 0.0148(9) 0.0048(7) -0.0031(8) -0.0162(8) C5S 0.0258(11) 0.0174(9) 0.0216(10) -0.0029(7) -0.0056(8) -0.0076(8) C6S 0.0231(10) 0.0155(8) 0.0231(10) -0.0012(7) -0.0038(8) -0.0107(7) C18 0.0165(10) 0.0164(8) 0.0373(12) -0.0015(8) -0.0070(9) -0.0072(7) C17 0.0237(11) 0.0178(8) 0.0243(10) -0.0020(7) -0.0107(8) -0.0063(7) C4S 0.0242(11) 0.0177(9) 0.0230(10) 0.0012(7) -0.0082(8) -0.0050(8) C19 0.0231(11) 0.0230(9) 0.0228(10) -0.0016(8) 0.0006(8) -0.0130(8) N3S 0.0444(16) 0.0621(17) 0.0411(14) -0.0023(12) 0.0029(12) 0.0170(13) C7S 0.0396(16) 0.0417(14) 0.0270(12) -0.0022(10) 0.0000(11) 0.0081(12) C10S 0.0348(15) 0.0442(15) 0.0474(16) -0.0037(12) -0.0107(13) -0.0057(12) C9A 0.039(4) 0.060(5) 0.040(4) -0.028(3) -0.008(4) 0.009(3) C12S 0.040(2) 0.0241(15) 0.046(3) -0.0091(18) -0.012(2) -0.0004(13) C11A 0.060(5) 0.043(4) 0.063(5) 0.015(3) -0.025(4) -0.031(4) C8S 0.040(2) 0.0241(15) 0.046(3) -0.0091(18) -0.012(2) -0.0004(13) C9S 0.033(3) 0.030(3) 0.036(4) -0.019(2) -0.006(3) -0.001(2) C11S 0.037(3) 0.021(3) 0.047(4) -0.005(2) -0.012(3) -0.009(2) C8A 0.040(2) 0.0241(15) 0.046(3) -0.0091(18) -0.012(2) -0.0004(13) C12A 0.040(2) 0.0241(15) 0.046(3) -0.0091(18) -0.012(2) -0.0004(13) N4S 0.0310(12) 0.0360(11) 0.0388(12) -0.0152(9) -0.0002(10) 0.0016(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 O4 S2 C8 103.63(8) O5 S2 O4 111.60(8) O5 S2 C8 106.58(8) O6 S2 O4 111.69(8) O6 S2 O5 115.75(9) O6 S2 C8 106.58(8) O1 S1 O2 119.54(8) O1 S1 N1 110.51(8) O1 S1 C1 110.56(9) O2 S1 N1 108.85(8) O2 S1 C1 111.90(8) N1 S1 C1 92.04(8) C14 N2 C15 123.90(16) H3A N3 H3B 120.0 C15 N3 H3A 120.0 C15 N3 H3B 120.0 C14 N1 S1 119.07(12) C14 N1 C7 127.11(15) C7 N1 S1 113.48(13) C15 N4 C16 122.85(16) C15 N4 C20 123.58(15) C20 N4 C16 113.56(15) C2S N2S C6S 115.64(15) C1S N2S C2S 116.98(16) C1S N2S C6S 117.92(16) N3 C15 N2 119.01(17) N3 C15 N4 124.35(17) N4 C15 N2 116.28(16) C9 C8 S2 118.49(14) C9 C8 C13 119.32(17) C13 C8 S2 122.13(13) C8 C9 H9 119.8 C10 C9 C8 120.49(17) C10 C9 H9 119.8 N2 C14 N1 114.80(16) N2 C14 C13 126.60(17) N1 C14 C13 118.34(15) C8 C13 C14 124.08(16) C12 C13 C8 119.68(16) C12 C13 C14 116.23(15) C1 C6 C7 114.22(17) C1 C6 C5 120.23(18) C5 C6 C7 125.47(17) O3 C7 N1 124.01(18) O3 C7 C6 127.41(17) N1 C7 C6 108.56(15) C6 C1 S1 111.47(15) C6 C1 C2 122.91(18) C2 C1 S1 125.53(15) C9 C10 H10 119.9 C9 C10 C11 120.28(17) C11 C10 H10 119.9 C10 C11 H11 120.3 C12 C11 C10 119.44(18) C12 C11 H11 120.3 C1 C2 H2 121.5 C1 C2 C3 116.93(18) C3 C2 H2 121.5 C13 C12 H12 119.6 C11 C12 C13 120.74(17) C11 C12 H12 119.6 C6 C5 H5 121.2 C4 C5 C6 117.56(18) C4 C5 H5 121.2 C5 C4 H4 119.3 C5 C4 C3 121.45(18) C3 C4 H4 119.3 C2 C3 H3 119.5 C4 C3 C2 120.92(19) C4 C3 H3 119.5 N4 C16 H16A 109.7 N4 C16 H16B 109.7 N4 C16 C17 109.77(16) H16A C16 H16B 108.2 C17 C16 H16A 109.7 C17 C16 H16B 109.7 N2S C2S H2SA 110.0 N2S C2S H2SB 110.0 N2S C2S C3S 108.69(16) H2SA C2S H2SB 108.3 C3S C2S H2SA 110.0 C3S C2S H2SB 110.0 N1S C1S N2S 178.2(3) C2S C3S H3SA 109.5 C2S C3S H3SB 109.5 C2S C3S C4S 110.89(17) H3SA C3S H3SB 108.0 C4S C3S H3SA 109.5 C4S C3S H3SB 109.5 N4 C20 H20A 109.6 N4 C20 H20B 109.6 N4 C20 C19 110.06(16) H20A C20 H20B 108.2 C19 C20 H20A 109.6 C19 C20 H20B 109.6 H5SA C5S H5SB 108.1 C6S C5S H5SA 109.5 C6S C5S H5SB 109.5 C6S C5S C4S 110.81(17) C4S C5S H5SA 109.5 C4S C5S H5SB 109.5 N2S C6S C5S 109.49(16) N2S C6S H6SA 109.8 N2S C6S H6SB 109.8 C5S C6S H6SA 109.8 C5S C6S H6SB 109.8 H6SA C6S H6SB 108.2 H18A C18 H18B 108.1 C17 C18 H18A 109.6 C17 C18 H18B 109.6 C19 C18 H18A 109.6 C19 C18 H18B 109.6 C19 C18 C17 110.32(16) C16 C17 C18 109.93(16) C16 C17 H17A 109.7 C16 C17 H17B 109.7 C18 C17 H17A 109.7 C18 C17 H17B 109.7 H17A C17 H17B 108.2 C3S C4S C5S 110.46(16) C3S C4S H4SA 109.6 C3S C4S H4SB 109.6 C5S C4S H4SA 109.6 C5S C4S H4SB 109.6 H4SA C4S H4SB 108.1 C20 C19 H19A 109.5 C20 C19 H19B 109.5 C18 C19 C20 110.76(17) C18 C19 H19A 109.5 C18 C19 H19B 109.5 H19A C19 H19B 108.1 N3S C7S N4S 179.7(4) H10A C10S H10B 108.4 H10C C10S H10D 107.5 C9A C10S H10A 110.1 C9A C10S H10B 110.1 C9A C10S C11A 108.0(5) C11A C10S H10A 110.1 C11A C10S H10B 110.1 C9S C10S H10C 108.5 C9S C10S H10D 108.5 C11S C10S H10C 108.5 C11S C10S H10D 108.5 C11S C10S C9S 115.0(4) C10S C9A H9AA 108.1 C10S C9A H9AB 108.1 C10S C9A C8A 116.7(6) H9AA C9A H9AB 107.3 C8A C9A H9AA 108.1 C8A C9A H9AB 108.1 H12A C12S H12B 107.7 C11S C12S H12A 108.8 C11S C12S H12B 108.8 N4S C12S H12A 108.8 N4S C12S H12B 108.8 N4S C12S C11S 114.0(5) C10S C11A H11A 108.4 C10S C11A H11B 108.4 H11A C11A H11B 107.5 C12A C11A C10S 115.5(5) C12A C11A H11A 108.4 C12A C11A H11B 108.4 H8SA C8S H8SB 107.6 C9S C8S H8SA 108.6 C9S C8S H8SB 108.6 N4S C8S H8SA 108.6 N4S C8S H8SB 108.6 N4S C8S C9S 114.6(6) C10S C9S H9SA 110.0 C10S C9S H9SB 110.0 C8S C9S C10S 108.3(5) C8S C9S H9SA 110.0 C8S C9S H9SB 110.0 H9SA C9S H9SB 108.4 C10S C11S C12S 109.3(5) C10S C11S H11C 109.8 C10S C11S H11D 109.8 C12S C11S H11C 109.8 C12S C11S H11D 109.8 H11C C11S H11D 108.3 C9A C8A H8AA 110.2 C9A C8A H8AB 110.2 H8AA C8A H8AB 108.5 N4S C8A C9A 107.4(6) N4S C8A H8AA 110.2 N4S C8A H8AB 110.2 C11A C12A H12C 110.0 C11A C12A H12D 110.0 H12C C12A H12D 108.3 N4S C12A C11A 108.6(5) N4S C12A H12C 110.0 N4S C12A H12D 110.0 C7S N4S C12S 123.0(3) C7S N4S C8S 119.9(4) C7S N4S C8A 116.0(4) C7S N4S C12A 115.1(3) C8S N4S C12S 112.6(5) C12A N4S C8A 123.9(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S2 O4 1.4787(12) S2 O5 1.4457(14) S2 O6 1.4420(14) S2 C8 1.7854(19) S1 O1 1.4237(13) S1 O2 1.4282(14) S1 N1 1.7245(16) S1 C1 1.750(2) O3 C7 1.205(2) N2 C15 1.391(2) N2 C14 1.278(2) N3 H3A 0.8600 N3 H3B 0.8600 N3 C15 1.316(2) N1 C14 1.387(2) N1 C7 1.432(2) N4 C15 1.320(2) N4 C16 1.477(2) N4 C20 1.476(2) N2S C2S 1.476(2) N2S C1S 1.334(3) N2S C6S 1.477(2) N1S C1S 1.156(3) C8 C9 1.396(2) C8 C13 1.402(2) C9 H9 0.9300 C9 C10 1.388(3) C14 C13 1.501(2) C13 C12 1.395(3) C6 C7 1.474(3) C6 C1 1.384(3) C6 C5 1.398(3) C1 C2 1.384(3) C10 H10 0.9300 C10 C11 1.394(3) C11 H11 0.9300 C11 C12 1.388(3) C2 H2 0.9300 C2 C3 1.396(3) C12 H12 0.9300 C5 H5 0.9300 C5 C4 1.395(3) C4 H4 0.9300 C4 C3 1.396(3) C3 H3 0.9300 C16 H16A 0.9700 C16 H16B 0.9700 C16 C17 1.519(3) C2S H2SA 0.9700 C2S H2SB 0.9700 C2S C3S 1.521(3) C3S H3SA 0.9700 C3S H3SB 0.9700 C3S C4S 1.524(3) C20 H20A 0.9700 C20 H20B 0.9700 C20 C19 1.525(3) C5S H5SA 0.9700 C5S H5SB 0.9700 C5S C6S 1.521(3) C5S C4S 1.530(3) C6S H6SA 0.9700 C6S H6SB 0.9700 C18 H18A 0.9700 C18 H18B 0.9700 C18 C17 1.523(3) C18 C19 1.522(3) C17 H17A 0.9700 C17 H17B 0.9700 C4S H4SA 0.9700 C4S H4SB 0.9700 C19 H19A 0.9700 C19 H19B 0.9700 N3S C7S 1.147(4) C7S N4S 1.335(4) C10S H10A 0.9700 C10S H10B 0.9700 C10S H10C 0.9700 C10S H10D 0.9700 C10S C9A 1.497(8) C10S C11A 1.576(8) C10S C9S 1.520(7) C10S C11S 1.458(6) C9A H9AA 0.9700 C9A H9AB 0.9700 C9A C8A 1.512(12) C12S H12A 0.9700 C12S H12B 0.9700 C12S C11S 1.507(9) C12S N4S 1.506(7) C11A H11A 0.9700 C11A H11B 0.9700 C11A C12A 1.515(11) C8S H8SA 0.9700 C8S H8SB 0.9700 C8S C9S 1.518(10) C8S N4S 1.438(7) C9S H9SA 0.9700 C9S H9SB 0.9700 C11S H11C 0.9700 C11S H11D 0.9700 C8A H8AA 0.9700 C8A H8AB 0.9700 C8A N4S 1.470(7) C12A H12C 0.9700 C12A H12D 0.9700 C12A N4S 1.409(7)