#------------------------------------------------------------------------------ #$Date: 2019-08-20 05:34:51 +0300 (Tue, 20 Aug 2019) $ #$Revision: 217606 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058767.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_7058767 loop_ _publ_author_name 'Xi Jia Ai Ti, Re He Man' 'Liu, Yong-Chun' 'Li, Xiao-Xiao' 'Zhao, Zhi-Gang' _publ_section_title ; Highly N2-selective allylation of NH-1,2,3-triazoles with allenamides mediated by N-iodosuccinimide ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ03014J _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_moiety 'C26 H24 F I N4 O2 S' _chemical_formula_sum 'C26 H24 F I N4 O2 S' _chemical_formula_weight 602.45 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-03-06 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-04-11 deposited with the CCDC. 2019-08-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.6016(4) _cell_length_b 24.2609(6) _cell_length_c 6.07906(11) _cell_measurement_reflns_used 3534 _cell_measurement_temperature 150 _cell_measurement_theta_max 72.4600 _cell_measurement_theta_min 6.0780 _cell_volume 2448.46(10) _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment air _diffrn_ambient_temperature 150 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9595 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -31.00 53.00 1.0000 1.4000 omega____ theta____ kappa____ phi______ frames - 36.2921 -57.0000 30.0000 84 #__ type_ start__ end____ width___ exp.time_ 2 omega 10.00 104.00 1.0000 1.4000 omega____ theta____ kappa____ phi______ frames - 36.2921 77.0000 60.0000 94 #__ type_ start__ end____ width___ exp.time_ 3 omega 20.00 104.00 1.0000 1.4000 omega____ theta____ kappa____ phi______ frames - 36.2921 57.0000 -60.0000 84 #__ type_ start__ end____ width___ exp.time_ 4 omega 57.00 94.00 1.0000 5.5900 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 30.0000 37 #__ type_ start__ end____ width___ exp.time_ 5 omega 23.00 90.00 1.0000 1.4000 omega____ theta____ kappa____ phi______ frames - 36.2921 -125.0000 -180.0000 67 #__ type_ start__ end____ width___ exp.time_ 6 omega 57.00 150.00 1.0000 5.5900 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 30.0000 93 #__ type_ start__ end____ width___ exp.time_ 7 omega 117.00 149.00 1.0000 5.5900 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 30.0000 32 #__ type_ start__ end____ width___ exp.time_ 8 omega 90.00 177.00 1.0000 5.5900 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 -120.0000 87 #__ type_ start__ end____ width___ exp.time_ 9 omega 71.00 109.00 1.0000 5.5900 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -150.0000 38 #__ type_ start__ end____ width___ exp.time_ 10 omega 46.00 120.00 1.0000 5.5900 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 90.0000 74 #__ type_ start__ end____ width___ exp.time_ 11 omega 48.00 74.00 1.0000 5.5900 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 120.0000 26 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Gemini, Dual, Cu at zero, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0878534000 _diffrn_orient_matrix_UB_12 -0.0201753000 _diffrn_orient_matrix_UB_13 -0.0141549000 _diffrn_orient_matrix_UB_21 -0.0298182000 _diffrn_orient_matrix_UB_22 0.0598794000 _diffrn_orient_matrix_UB_23 0.0208108000 _diffrn_orient_matrix_UB_31 0.0024176000 _diffrn_orient_matrix_UB_32 0.0060537000 _diffrn_orient_matrix_UB_33 -0.2522354000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_unetI/netI 0.0552 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 7874 _diffrn_reflns_point_group_measured_fraction_full 0.758 _diffrn_reflns_point_group_measured_fraction_max 0.732 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.618 _diffrn_reflns_theta_min 5.329 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 11.406 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.28480 _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 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.634 _exptl_crystal_description needle _exptl_crystal_F_000 1208 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 1.587 _refine_diff_density_min -1.247 _refine_diff_density_rms 0.166 _refine_ls_abs_structure_details ; Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.021(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 318 _refine_ls_number_reflns 3571 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0575 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1226P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1498 _refine_ls_wR_factor_ref 0.1522 _reflns_Friedel_coverage 0.367 _reflns_Friedel_fraction_full 0.466 _reflns_Friedel_fraction_max 0.437 _reflns_number_gt 3432 _reflns_number_total 3571 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj03014j2.cif _cod_data_source_block lxx-190305-150k _cod_original_cell_volume 2448.47(10) _cod_database_code 7058767 _shelx_shelxl_version_number 2014/7 _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 99.30 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C8(H8) 2.b Secondary CH2 refined with riding coordinates: C7(H7A,H7B) 2.c Aromatic/amide H refined with riding coordinates: C9(H9), C5(H5), C1(H1), C12(H12), C16(H16), C4(H4), C2(H2), C15(H15), C13(H13), C22(H22), C25(H25), C24(H24), C21(H21) 2.d X=CH2 refined with riding coordinates: C19(H19A,H19B) 2.e Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C26(H26A,H26B,H26C) ; _shelx_res_file ; lxx-190305-150k.res created by SHELXL-2014/7 TITL lxx-190305-150k in Pna21 #33 REM reset to Pna21 #33 CELL 1.54184 16.601641 24.260939 6.079065 90 90 90 ZERR 4 0.000435 0.000592 0.000112 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H F I N O S UNIT 104 96 4 4 16 8 4 L.S. 10 PLAN 20 TEMP -123.15 BOND fmap 2 acta REM REM REM WGHT 0.122600 FVAR 3.45489 S1 7 1.295452 0.594679 1.064270 11.00000 0.01788 0.02915 = 0.02628 0.00156 -0.00772 -0.00111 N2 5 1.145319 0.674349 0.902092 11.00000 0.01773 0.01589 = 0.02970 -0.00040 0.00180 0.00211 N3 5 1.158263 0.675676 0.686783 11.00000 0.02569 0.02488 = 0.02166 0.00037 0.00224 -0.00055 C7 1 1.195415 0.556126 0.757333 11.00000 0.01744 0.01884 = 0.03221 -0.00270 -0.00785 0.00127 AFIX 23 H7A 2 1.237083 0.571208 0.657587 11.00000 -1.20000 H7B 2 1.142158 0.564870 0.692910 11.00000 -1.20000 AFIX 0 O1 6 1.338199 0.544846 1.018447 11.00000 0.01953 0.03021 = 0.04792 0.00602 -0.00426 0.00562 N4 5 1.123800 0.723009 0.992009 11.00000 0.02189 0.01451 = 0.02374 0.00026 0.00220 -0.00041 C10 1 1.125399 0.757180 0.820058 11.00000 0.01560 0.01875 = 0.03061 0.00066 0.00018 -0.00140 C11 1 1.105206 0.816604 0.849347 11.00000 0.01406 0.01974 = 0.02726 0.00135 0.00166 -0.00188 N1 5 1.202121 0.583731 0.970630 11.00000 0.01671 0.02034 = 0.02835 0.00311 -0.00249 0.00266 C9 1 1.147859 0.727866 0.633323 11.00000 0.02332 0.02437 = 0.01853 0.00457 0.00407 -0.00057 AFIX 43 H9 2 1.154614 0.742992 0.490364 11.00000 -1.20000 AFIX 0 C8 1 1.142489 0.624369 1.035138 11.00000 0.02839 0.01635 = 0.01955 0.00372 0.00376 -0.00227 AFIX 13 H8 2 1.154299 0.635176 1.190571 11.00000 -1.20000 AFIX 0 C6 1 1.204846 0.493509 0.767418 11.00000 0.01593 0.02396 = 0.02812 -0.00312 -0.00755 0.00142 C3 1 1.219485 0.380897 0.763720 11.00000 0.01673 0.02086 = 0.03826 -0.00781 -0.00711 0.00181 C5 1 1.189505 0.464200 0.954543 11.00000 0.02336 0.02371 = 0.03374 -0.00525 -0.00090 0.00160 AFIX 43 H5 2 1.174113 0.483017 1.084983 11.00000 -1.20000 AFIX 0 C1 1 1.227809 0.466788 0.576909 11.00000 0.01902 0.02948 = 0.03216 -0.00090 0.00343 0.00168 AFIX 43 H1 2 1.238465 0.487451 0.447393 11.00000 -1.20000 AFIX 0 C12 1 1.119522 0.854788 0.684327 11.00000 0.02187 0.02166 = 0.02644 0.00407 0.00110 -0.00095 AFIX 43 H12 2 1.140945 0.843085 0.547152 11.00000 -1.20000 AFIX 0 C18 1 1.057779 0.600337 1.030303 11.00000 0.02421 0.01905 = 0.02064 0.01106 0.00661 0.00491 C16 1 1.071351 0.835173 1.049195 11.00000 0.02056 0.02193 = 0.03165 0.00589 0.00142 0.00201 AFIX 43 H16 2 1.059164 0.809423 1.162122 11.00000 -1.20000 AFIX 0 C4 1 1.196226 0.406839 0.955984 11.00000 0.02847 0.02865 = 0.03010 -0.00057 0.00058 -0.00797 AFIX 43 H4 2 1.185135 0.386228 1.085359 11.00000 -1.20000 AFIX 0 C2 1 1.235464 0.409021 0.574141 11.00000 0.03165 0.02873 = 0.03152 -0.00926 0.00732 -0.00374 AFIX 43 H2 2 1.251283 0.390152 0.444200 11.00000 -1.20000 AFIX 0 F1 3 1.228538 0.324808 0.764260 11.00000 0.03643 0.02025 = 0.06213 -0.00718 -0.00100 -0.00016 C15 1 1.055998 0.889948 1.081244 11.00000 0.01785 0.02889 = 0.02470 -0.00342 0.00550 0.00516 AFIX 43 H15 2 1.033841 0.901899 1.217205 11.00000 -1.20000 AFIX 0 C17 1 1.057794 0.989147 0.960331 11.00000 0.03360 0.02212 = 0.02946 0.00261 0.00643 0.00104 AFIX 137 H17A 2 1.083629 0.999748 1.098969 11.00000 -1.50000 H17B 2 0.999737 0.996027 0.970156 11.00000 -1.50000 H17C 2 1.080574 1.010928 0.839658 11.00000 -1.50000 AFIX 0 C13 1 1.102385 0.910735 0.719781 11.00000 0.01659 0.02510 = 0.02468 0.00956 0.00174 -0.00433 AFIX 43 H13 2 1.111708 0.936619 0.605314 11.00000 -1.20000 AFIX 0 C19 1 1.000977 0.612017 0.886711 11.00000 0.02816 0.03465 = 0.06406 0.01220 -0.00448 -0.00273 AFIX 93 H19A 2 1.011173 0.637715 0.772134 11.00000 -1.20000 H19B 2 0.949773 0.594751 0.897621 11.00000 -1.20000 AFIX 0 C14 1 1.072379 0.928487 0.917397 11.00000 0.01009 0.02403 = 0.02859 0.00309 -0.00299 -0.00277 O2 6 1.286457 0.613786 1.280587 11.00000 0.03095 0.05633 = 0.02355 0.00671 -0.01209 -0.01292 C20 1 1.339435 0.647632 0.906297 11.00000 0.01183 0.02844 = 0.02990 -0.00151 -0.00442 -0.00221 C22 1 1.362393 0.743007 0.832882 11.00000 0.02114 0.02081 = 0.04276 -0.00884 -0.00297 -0.00687 AFIX 43 H22 2 1.357991 0.780627 0.874541 11.00000 -1.20000 AFIX 0 C25 1 1.380161 0.633776 0.714688 11.00000 0.01399 0.02628 = 0.04245 -0.00505 -0.00073 0.00272 AFIX 43 H25 2 1.386382 0.596221 0.673832 11.00000 -1.20000 AFIX 0 C24 1 1.411486 0.674999 0.584272 11.00000 0.01349 0.03345 = 0.02897 -0.00663 -0.00325 -0.00470 AFIX 43 H24 2 1.440146 0.665635 0.454276 11.00000 -1.20000 AFIX 0 C23 1 1.401739 0.729609 0.640143 11.00000 0.01979 0.02900 = 0.03125 -0.00266 -0.00637 0.00252 C21 1 1.329551 0.703259 0.965421 11.00000 0.01893 0.03019 = 0.03128 -0.01584 0.00305 -0.00543 AFIX 43 H21 2 1.300701 0.713067 1.094580 11.00000 -1.20000 AFIX 0 C26 1 1.434635 0.773595 0.487061 11.00000 0.02906 0.03401 = 0.04969 0.00571 -0.01146 -0.00909 AFIX 137 H26A 2 1.493381 0.770280 0.478408 11.00000 -1.50000 H26B 2 1.420386 0.810127 0.543783 11.00000 -1.50000 H26C 2 1.411381 0.768783 0.340137 11.00000 -1.50000 AFIX 0 I1 4 1.030880 0.546851 1.292130 11.00000 0.02586 0.03147 = 0.02644 0.00385 0.00199 -0.00901 HKLF 4 REM lxx-190305-150k in Pna21 #33 REM R1 = 0.0575 for 3432 Fo > 4sig(Fo) and 0.0588 for all 3571 data REM 318 parameters refined using 1 restraints END WGHT 0.1225 0.0000 REM Highest difference peak 1.587, deepest hole -1.247, 1-sigma level 0.166 Q1 1 1.0310 0.5469 1.4569 11.00000 0.05 1.59 Q2 1 1.0312 0.5478 1.1259 11.00000 0.05 1.51 Q3 1 1.0406 0.5212 0.9266 11.00000 0.05 0.93 Q4 1 1.0396 0.5222 0.6597 11.00000 0.05 0.87 Q5 1 1.0781 0.4510 0.9437 11.00000 0.05 0.75 Q6 1 1.0425 0.5735 0.9221 11.00000 0.05 0.74 Q7 1 1.1433 0.5411 1.1433 11.00000 0.05 0.73 Q8 1 1.0070 0.5223 1.1860 11.00000 0.05 0.72 Q9 1 0.9641 0.5207 0.9969 11.00000 0.05 0.71 Q10 1 0.9779 0.5471 1.2915 11.00000 0.05 0.71 Q11 1 1.1401 0.5438 0.4514 11.00000 0.05 0.71 Q12 1 1.0400 0.4794 1.0821 11.00000 0.05 0.68 Q13 1 0.9165 0.5502 1.1428 11.00000 0.05 0.67 Q14 1 1.0440 0.5717 0.6633 11.00000 0.05 0.63 Q15 1 0.9266 0.5974 1.2935 11.00000 0.05 0.61 Q16 1 1.0770 0.4995 0.8043 11.00000 0.05 0.60 Q17 1 1.1618 0.5301 0.3554 11.00000 0.05 0.55 Q18 1 0.9337 0.5389 0.7187 11.00000 0.05 0.54 Q19 1 1.1786 0.5961 0.9518 11.00000 0.05 0.54 Q20 1 1.0283 0.5888 1.3052 11.00000 0.05 0.54 ; _shelx_res_checksum 52799 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, 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 S1 S 1.29545(12) 0.59468(8) 1.0643(3) 0.0244(4) Uani 1 1 d . N2 N 1.1453(4) 0.6743(3) 0.9021(12) 0.0211(14) Uani 1 1 d . N3 N 1.1583(5) 0.6757(3) 0.6868(12) 0.0241(15) Uani 1 1 d . C7 C 1.1954(5) 0.5561(3) 0.7573(16) 0.0228(17) Uani 1 1 d . H7A H 1.2371 0.5712 0.6576 0.027 Uiso 1 1 calc R H7B H 1.1422 0.5649 0.6929 0.027 Uiso 1 1 calc R O1 O 1.3382(4) 0.5448(2) 1.0184(14) 0.0326(16) Uani 1 1 d . N4 N 1.1238(4) 0.7230(2) 0.9920(12) 0.0200(13) Uani 1 1 d . C10 C 1.1254(4) 0.7572(3) 0.8201(14) 0.0217(16) Uani 1 1 d . C11 C 1.1052(4) 0.8166(3) 0.8493(13) 0.0204(15) Uani 1 1 d . N1 N 1.2021(4) 0.5837(2) 0.9706(12) 0.0218(13) Uani 1 1 d . C9 C 1.1479(5) 0.7279(3) 0.6333(13) 0.0221(16) Uani 1 1 d . H9 H 1.1546 0.7430 0.4904 0.026 Uiso 1 1 calc R C8 C 1.1425(5) 0.6244(3) 1.0351(12) 0.0214(15) Uani 1 1 d . H8 H 1.1543 0.6352 1.1906 0.026 Uiso 1 1 calc R C6 C 1.2048(4) 0.4935(3) 0.7674(15) 0.0227(15) Uani 1 1 d . C3 C 1.2195(4) 0.3809(3) 0.7637(18) 0.0253(16) Uani 1 1 d . C5 C 1.1895(5) 0.4642(3) 0.9545(16) 0.0269(17) Uani 1 1 d . H5 H 1.1741 0.4830 1.0850 0.032 Uiso 1 1 calc R C1 C 1.2278(5) 0.4668(4) 0.5769(16) 0.0269(17) Uani 1 1 d . H1 H 1.2385 0.4875 0.4474 0.032 Uiso 1 1 calc R C12 C 1.1195(5) 0.8548(3) 0.6843(14) 0.0233(16) Uani 1 1 d . H12 H 1.1409 0.8431 0.5472 0.028 Uiso 1 1 calc R C18 C 1.0578(5) 0.6003(3) 1.0303(13) 0.0213(15) Uani 1 1 d . C16 C 1.0714(5) 0.8352(3) 1.0492(15) 0.0247(16) Uani 1 1 d . H16 H 1.0592 0.8094 1.1621 0.030 Uiso 1 1 calc R C4 C 1.1962(5) 0.4068(3) 0.9560(16) 0.0291(17) Uani 1 1 d . H4 H 1.1851 0.3862 1.0854 0.035 Uiso 1 1 calc R C2 C 1.2355(6) 0.4090(4) 0.5741(17) 0.0306(18) Uani 1 1 d . H2 H 1.2513 0.3902 0.4442 0.037 Uiso 1 1 calc R F1 F 1.2285(3) 0.32481(17) 0.7643(12) 0.0396(13) Uani 1 1 d . C15 C 1.0560(5) 0.8899(3) 1.0812(14) 0.0238(16) Uani 1 1 d . H15 H 1.0338 0.9019 1.2172 0.029 Uiso 1 1 calc R C17 C 1.0578(6) 0.9891(3) 0.9603(15) 0.0284(17) Uani 1 1 d . H17A H 1.0836 0.9997 1.0990 0.043 Uiso 1 1 calc GR H17B H 0.9997 0.9960 0.9702 0.043 Uiso 1 1 calc GR H17C H 1.0806 1.0109 0.8397 0.043 Uiso 1 1 calc GR C13 C 1.1024(5) 0.9107(3) 0.7198(13) 0.0221(16) Uani 1 1 d . H13 H 1.1117 0.9366 0.6053 0.027 Uiso 1 1 calc R C19 C 1.0010(6) 0.6120(4) 0.887(2) 0.042(2) Uani 1 1 d . H19A H 1.0112 0.6377 0.7721 0.051 Uiso 1 1 calc R H19B H 0.9498 0.5948 0.8976 0.051 Uiso 1 1 calc R C14 C 1.0724(4) 0.9285(3) 0.9174(14) 0.0209(15) Uani 1 1 d . O2 O 1.2865(4) 0.6138(3) 1.2806(13) 0.0369(14) Uani 1 1 d . C20 C 1.3394(5) 0.6476(3) 0.9063(14) 0.0234(16) Uani 1 1 d . C22 C 1.3624(5) 0.7430(3) 0.8329(15) 0.0282(19) Uani 1 1 d . H22 H 1.3580 0.7806 0.8745 0.034 Uiso 1 1 calc R C25 C 1.3802(5) 0.6338(3) 0.7147(15) 0.0276(18) Uani 1 1 d . H25 H 1.3864 0.5962 0.6738 0.033 Uiso 1 1 calc R C24 C 1.4115(4) 0.6750(3) 0.5843(15) 0.0253(16) Uani 1 1 d . H24 H 1.4401 0.6656 0.4543 0.030 Uiso 1 1 calc R C23 C 1.4017(5) 0.7296(3) 0.6401(15) 0.0267(16) Uani 1 1 d . C21 C 1.3296(5) 0.7033(3) 0.9654(14) 0.0268(17) Uani 1 1 d . H21 H 1.3007 0.7131 1.0946 0.032 Uiso 1 1 calc R C26 C 1.4346(6) 0.7736(4) 0.4871(19) 0.038(2) Uani 1 1 d . H26A H 1.4934 0.7703 0.4784 0.056 Uiso 1 1 calc GR H26B H 1.4204 0.8101 0.5438 0.056 Uiso 1 1 calc GR H26C H 1.4114 0.7688 0.3401 0.056 Uiso 1 1 calc GR I1 I 1.03088(3) 0.54685(2) 1.29213(15) 0.0279(2) Uani 1 1 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 S1 0.0179(8) 0.0292(8) 0.0263(9) 0.0016(8) -0.0077(7) -0.0011(7) N2 0.018(3) 0.016(3) 0.030(4) 0.000(3) 0.002(3) 0.002(2) N3 0.026(4) 0.025(3) 0.022(3) 0.000(3) 0.002(3) -0.001(3) C7 0.017(3) 0.019(3) 0.032(5) -0.003(3) -0.008(4) 0.001(2) O1 0.020(3) 0.030(3) 0.048(4) 0.006(2) -0.004(3) 0.006(2) N4 0.022(3) 0.015(2) 0.024(3) 0.000(2) 0.002(3) 0.000(2) C10 0.016(3) 0.019(3) 0.031(5) 0.001(3) 0.000(3) -0.001(2) C11 0.014(3) 0.020(3) 0.027(4) 0.001(3) 0.002(3) -0.002(3) N1 0.017(3) 0.020(3) 0.028(3) 0.003(3) -0.002(3) 0.003(2) C9 0.023(4) 0.024(3) 0.019(3) 0.005(3) 0.004(3) -0.001(3) C8 0.028(4) 0.016(3) 0.020(3) 0.004(3) 0.004(3) -0.002(3) C6 0.016(3) 0.024(3) 0.028(4) -0.003(4) -0.008(4) 0.001(2) C3 0.017(3) 0.021(3) 0.038(5) -0.008(4) -0.007(4) 0.002(2) C5 0.023(4) 0.024(3) 0.034(5) -0.005(4) -0.001(4) 0.002(3) C1 0.019(4) 0.029(3) 0.032(4) -0.001(4) 0.003(3) 0.002(3) C12 0.022(4) 0.022(3) 0.026(4) 0.004(3) 0.001(3) -0.001(3) C18 0.024(4) 0.019(3) 0.021(4) 0.011(3) 0.007(3) 0.005(3) C16 0.021(3) 0.022(3) 0.032(4) 0.006(3) 0.001(3) 0.002(3) C4 0.028(4) 0.029(4) 0.030(4) -0.001(3) 0.001(4) -0.008(3) C2 0.032(5) 0.029(4) 0.032(4) -0.009(4) 0.007(4) -0.004(3) F1 0.036(3) 0.0202(18) 0.062(4) -0.007(3) -0.001(3) -0.0002(18) C15 0.018(4) 0.029(4) 0.025(4) -0.003(3) 0.006(3) 0.005(3) C17 0.034(5) 0.022(3) 0.029(4) 0.003(3) 0.006(4) 0.001(3) C13 0.017(3) 0.025(3) 0.025(4) 0.010(3) 0.002(3) -0.004(3) C19 0.028(5) 0.035(4) 0.064(7) 0.012(5) -0.004(5) -0.003(4) C14 0.010(3) 0.024(3) 0.029(4) 0.003(3) -0.003(3) -0.003(3) O2 0.031(3) 0.056(3) 0.024(3) 0.007(4) -0.012(4) -0.013(3) C20 0.012(3) 0.028(3) 0.030(4) -0.002(3) -0.004(3) -0.002(3) C22 0.021(3) 0.021(3) 0.043(6) -0.009(3) -0.003(3) -0.007(3) C25 0.014(4) 0.026(3) 0.042(5) -0.005(3) -0.001(3) 0.003(3) C24 0.013(3) 0.033(4) 0.029(4) -0.007(3) -0.003(3) -0.005(3) C23 0.020(4) 0.029(4) 0.031(4) -0.003(3) -0.006(3) 0.003(3) C21 0.019(4) 0.030(4) 0.031(4) -0.016(4) 0.003(3) -0.005(3) C26 0.029(4) 0.034(4) 0.050(6) 0.006(4) -0.011(4) -0.009(4) I1 0.0259(3) 0.0315(3) 0.0264(3) 0.0038(2) 0.0020(3) -0.00901(16) 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 '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 O1 S1 N1 105.0(4) O1 S1 C20 107.7(4) N1 S1 C20 108.3(4) O2 S1 O1 121.0(5) O2 S1 N1 105.8(4) O2 S1 C20 108.3(4) N3 N2 N4 114.9(7) N3 N2 C8 124.9(7) N4 N2 C8 119.6(7) C9 N3 N2 104.2(7) N1 C7 C6 114.3(7) C10 N4 N2 102.8(6) N4 C10 C11 120.2(7) N4 C10 C9 109.1(6) C9 C10 C11 130.7(7) C12 C11 C10 121.4(7) C12 C11 C16 118.5(7) C16 C11 C10 120.0(7) C7 N1 S1 116.4(5) C8 N1 S1 115.6(5) C8 N1 C7 119.9(6) N3 C9 C10 109.0(7) N2 C8 C18 109.7(6) N1 C8 N2 113.1(6) N1 C8 C18 111.4(6) C5 C6 C7 122.1(8) C5 C6 C1 120.4(7) C1 C6 C7 117.5(8) C2 C3 C4 122.7(7) C2 C3 F1 118.5(9) F1 C3 C4 118.8(9) C6 C5 C4 120.6(8) C6 C1 C2 120.2(9) C11 C12 C13 120.0(8) C8 C18 I1 114.7(5) C19 C18 C8 126.3(7) C19 C18 I1 118.9(7) C15 C16 C11 120.5(7) C3 C4 C5 118.1(9) C3 C2 C1 118.0(9) C16 C15 C14 120.9(8) C14 C13 C12 120.8(7) C15 C14 C17 119.9(7) C13 C14 C15 119.1(7) C13 C14 C17 121.0(7) C25 C20 S1 118.9(6) C25 C20 C21 120.2(8) C21 C20 S1 120.8(7) C21 C22 C23 121.5(7) C24 C25 C20 119.4(7) C23 C24 C25 120.8(8) C22 C23 C26 121.7(8) C24 C23 C22 119.4(8) C24 C23 C26 118.9(9) C22 C21 C20 118.6(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.429(6) S1 N1 1.672(7) S1 O2 1.402(9) S1 C20 1.762(8) N2 N3 1.327(9) N2 N4 1.349(9) N2 C8 1.458(9) N3 C9 1.319(11) C7 N1 1.464(12) C7 C6 1.528(9) N4 C10 1.334(10) C10 C11 1.491(9) C10 C9 1.390(11) C11 C12 1.386(11) C11 C16 1.412(12) N1 C8 1.451(10) C8 C18 1.523(11) C6 C5 1.365(13) C6 C1 1.381(13) C3 C4 1.382(13) C3 C2 1.365(15) C3 F1 1.369(8) C5 C4 1.396(11) C1 C2 1.407(11) C12 C13 1.403(10) C18 C19 1.316(14) C18 I1 2.102(7) C16 C15 1.367(11) C15 C14 1.393(11) C17 C14 1.514(10) C13 C14 1.370(12) C20 C25 1.388(12) C20 C21 1.406(10) C22 C23 1.380(12) C22 C21 1.370(12) C25 C24 1.378(12) C24 C23 1.377(11) C23 C26 1.518(13)