#------------------------------------------------------------------------------ #$Date: 2017-12-13 07:22:47 +0200 (Wed, 13 Dec 2017) $ #$Revision: 204211 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156033.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_7156033 loop_ _publ_author_name 'Ma, Fanghui' 'Qian, Jing' 'Lu, Ping' 'Wang, Yanguang' _publ_section_title ; Convenient Synthesis of 2-Amino-3-(arylthio)indoles via Rh-Catalyzed Reaction of 3-Diazoindol-2-imines with Thioesters ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C7OB02597A _journal_year 2017 _chemical_formula_moiety 'C23 H19 F N2 O3 S2' _chemical_formula_sum 'C23 H19 F N2 O3 S2' _chemical_formula_weight 454.52 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2017-01-13 _audit_creation_method ; Olex2 1.2 (compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289) ; _audit_update_record ; 2017-07-21 deposited with the CCDC. 2017-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90.0 _cell_angle_beta 105.076(10) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 14.9465(16) _cell_length_b 9.9560(8) _cell_length_c 14.9447(12) _cell_measurement_reflns_used 5872 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.5387 _cell_measurement_theta_min 2.8028 _cell_volume 2147.3(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _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_temperature 293.15 _diffrn_detector_area_resol_mean 5.1796 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -48.00 42.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -12.7965 85.0000 26.0000 90 #__ type_ start__ end____ width___ exp.time_ 2 omega -87.00 16.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -12.7965 -77.0000 150.0000 103 #__ type_ start__ end____ width___ exp.time_ 3 omega -45.00 38.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -12.7965 85.0000 -88.0000 83 ; _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0394956000 _diffrn_orient_matrix_UB_12 -0.0356027000 _diffrn_orient_matrix_UB_13 0.0051602000 _diffrn_orient_matrix_UB_21 0.0209210000 _diffrn_orient_matrix_UB_22 -0.0614234000 _diffrn_orient_matrix_UB_23 -0.0075468000 _diffrn_orient_matrix_UB_31 0.0205682000 _diffrn_orient_matrix_UB_32 -0.0057389000 _diffrn_orient_matrix_UB_33 0.0482600000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_unetI/netI 0.0391 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 12822 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.348 _diffrn_reflns_theta_min 3.435 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90718 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.403 _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.206 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 3906 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0441 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.5528P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1048 _refine_ls_wR_factor_ref 0.1151 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3096 _reflns_number_total 3906 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ob02597a2.cif _cod_data_source_block 170113_mfh_451_132_3 _cod_original_cell_volume 2147.3(2) _cod_database_code 7156033 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula 'c10 h10 n2 o8 s1 f1' _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. ; _cell_oxdiff_angle_alpha 90.036(5) _cell_oxdiff_angle_beta 105.125(5) _cell_oxdiff_angle_gamma 90.039(5) _cell_oxdiff_length_a 14.9342(10) _cell_oxdiff_length_b 9.9581(6) _cell_oxdiff_length_c 14.9572(8) _cell_oxdiff_measurement_reflns_used 5633 _cell_oxdiff_volume 2147.3(2) _shelx_estimated_absorpt_t_max 0.905 _shelx_estimated_absorpt_t_min 0.876 _reflns_odcompleteness_completeness 99.74 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19), C21(H21), C22(H22) 2.b Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C23(H23A,H23B,H23C) ; _shelx_res_file ; TITL 170113_MFH_451_132_3 in P21/c #14 170113_mfh_451_132_3.res created by SHELXL-2016/6 at 11:47:14 on 13-Jan-2017 REM reset to P21/c #14 CELL 0.71073 14.94388 9.97245 14.94827 90 105.0672 90 ZERR 4 0.00164 0.00108 0.00168 0 0.0109 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O S UNIT 92 76 4 8 12 8 L.S. 10 PLAN 20 SIZE 0.48 0.4 0.36 TEMP 20 BOND $h htab fmap 2 acta SHEL 999 0.83 REM REM REM WGHT 0.049600 0.552800 FVAR 4.97593 S1 6 0.244804 0.533313 0.104044 11.00000 0.04993 0.05497 = 0.03544 0.00390 0.01416 0.00831 S2 6 0.182816 0.352294 -0.163649 11.00000 0.06742 0.04089 = 0.04391 -0.00652 0.02188 0.00087 F1 3 0.102866 -0.112425 0.035154 11.00000 0.10849 0.05284 = 0.08992 0.01605 0.03532 -0.00238 O1 5 -0.003755 0.403870 -0.154971 11.00000 0.05061 0.04724 = 0.07635 -0.00703 0.00185 -0.00686 O2 5 0.280199 0.374056 -0.139704 11.00000 0.06305 0.05775 = 0.09694 -0.01222 0.04333 -0.00039 O3 5 0.133293 0.341832 -0.258137 11.00000 0.11505 0.05616 = 0.03846 -0.00667 0.02185 -0.00287 N1 4 0.218145 0.690688 -0.142776 11.00000 0.04704 0.03848 = 0.03739 0.00496 0.00917 -0.00106 N2 4 0.141616 0.487084 -0.116890 11.00000 0.04576 0.03275 = 0.03709 -0.00317 0.00961 -0.00077 C1 1 0.358864 0.824758 0.067944 11.00000 0.04860 0.05977 = 0.06046 -0.01247 0.00283 -0.00342 AFIX 43 H1 2 0.374973 0.800463 0.130149 11.00000 -1.20000 AFIX 0 C2 1 0.392600 0.940928 0.038833 11.00000 0.05397 0.06303 = 0.09509 -0.02411 0.01061 -0.01909 AFIX 43 H2 2 0.432201 0.995463 0.082073 11.00000 -1.20000 AFIX 0 C3 1 0.368462 0.978108 -0.054147 11.00000 0.05933 0.05325 = 0.09922 -0.00082 0.02859 -0.01190 AFIX 43 H3 2 0.392214 1.057290 -0.071522 11.00000 -1.20000 AFIX 0 C4 1 0.311375 0.902179 -0.119948 11.00000 0.04799 0.04572 = 0.07010 0.00724 0.02050 -0.00085 AFIX 43 H4 2 0.295473 0.927896 -0.181879 11.00000 -1.20000 AFIX 0 C5 1 0.277445 0.784428 -0.091503 11.00000 0.03736 0.03788 = 0.04904 0.00261 0.01231 0.00282 C6 1 0.299938 0.744692 0.001582 11.00000 0.03386 0.04320 = 0.04853 -0.00357 0.00667 0.00272 C7 1 0.251926 0.621541 0.005795 11.00000 0.04095 0.03756 = 0.03727 0.00012 0.00869 0.00592 C8 1 0.203563 0.593567 -0.083105 11.00000 0.04010 0.03325 = 0.03775 0.00290 0.01113 0.00244 C9 1 0.346404 0.433027 0.134228 11.00000 0.04605 0.04588 = 0.03215 -0.00144 0.00612 0.00035 C10 1 0.351056 0.340841 0.203595 11.00000 0.06110 0.05333 = 0.04737 0.00703 0.01595 0.00352 AFIX 43 H10 2 0.303185 0.335929 0.232680 11.00000 -1.20000 AFIX 0 C11 1 0.425684 0.255691 0.230560 11.00000 0.08189 0.06087 = 0.05105 0.01342 0.00617 0.01663 AFIX 43 H11 2 0.428061 0.194128 0.277853 11.00000 -1.20000 AFIX 0 C12 1 0.495698 0.261171 0.188502 11.00000 0.06978 0.08739 = 0.05794 0.00538 0.00484 0.03218 AFIX 43 H12 2 0.546214 0.203733 0.206560 11.00000 -1.20000 AFIX 0 C13 1 0.491061 0.352064 0.119339 11.00000 0.06518 0.13579 = 0.08553 0.03242 0.03676 0.04104 AFIX 43 H13 2 0.538894 0.355684 0.090144 11.00000 -1.20000 AFIX 0 C14 1 0.417113 0.438816 0.091611 11.00000 0.06371 0.09402 = 0.06192 0.03011 0.02856 0.02363 AFIX 43 H14 2 0.415300 0.500518 0.044522 11.00000 -1.20000 AFIX 0 C15 1 0.046693 0.495067 -0.122116 11.00000 0.04684 0.03903 = 0.03876 0.00478 0.00400 -0.00073 C16 1 0.015137 0.620354 -0.085209 11.00000 0.04745 0.04596 = 0.06345 -0.00240 0.01350 0.00350 AFIX 137 H16A 2 0.046303 0.629448 -0.020697 11.00000 -1.50000 H16B 2 -0.050553 0.616114 -0.092527 11.00000 -1.50000 H16C 2 0.029344 0.696169 -0.118640 11.00000 -1.50000 AFIX 0 C17 1 0.156925 0.213694 -0.103532 11.00000 0.05399 0.03303 = 0.04164 -0.00536 0.01081 0.00409 C18 1 0.094038 0.120364 -0.148738 11.00000 0.07566 0.04528 = 0.05191 -0.00102 -0.00581 -0.00144 AFIX 43 H18 2 0.063579 0.132270 -0.210903 11.00000 -1.20000 AFIX 0 C19 1 0.076070 0.009242 -0.102106 11.00000 0.07140 0.04259 = 0.07487 -0.00228 -0.00141 -0.01052 AFIX 43 H19 2 0.034378 -0.055797 -0.132128 11.00000 -1.20000 AFIX 0 C20 1 0.120609 -0.003226 -0.011281 11.00000 0.06895 0.03770 = 0.06476 0.00271 0.02362 0.00475 C21 1 0.182571 0.087881 0.035418 11.00000 0.09252 0.04998 = 0.04226 -0.00169 0.00995 0.00253 AFIX 43 H21 2 0.211483 0.076201 0.097986 11.00000 -1.20000 AFIX 0 C22 1 0.201770 0.197888 -0.011649 11.00000 0.07512 0.04460 = 0.04769 -0.00904 0.00660 -0.00696 AFIX 43 H22 2 0.244831 0.261170 0.018526 11.00000 -1.20000 AFIX 0 C23 1 0.181911 0.693935 -0.242808 11.00000 0.07318 0.06406 = 0.03798 0.01355 0.00580 -0.00820 AFIX 137 H23A 2 0.232301 0.689101 -0.271519 11.00000 -1.50000 H23B 2 0.148275 0.775859 -0.260661 11.00000 -1.50000 H23C 2 0.141205 0.618992 -0.262366 11.00000 -1.50000 AFIX 0 HKLF 4 REM 170113_MFH_451_132_3 in P21/c #14 REM R1 = 0.0441 for 3096 Fo > 4sig(Fo) and 0.0580 for all 3906 data REM 282 parameters refined using 0 restraints END WGHT 0.0496 0.5527 REM Instructions for potential hydrogen bonds HTAB C22 S1 EQIV $1 -x, y+1/2, -z-1/2 HTAB C23 O1_$1 HTAB C23 S2 REM Highest difference peak 0.206, deepest hole -0.290, 1-sigma level 0.044 Q1 1 0.2006 0.7592 -0.2836 11.00000 0.05 0.21 Q2 1 0.2579 0.5814 -0.0290 11.00000 0.05 0.19 Q3 1 0.2156 0.5850 -0.2766 11.00000 0.05 0.18 Q4 1 0.2282 0.7897 -0.2569 11.00000 0.05 0.18 Q5 1 0.2595 0.5849 0.0479 11.00000 0.05 0.17 Q6 1 0.0811 0.7060 -0.2527 11.00000 0.05 0.17 Q7 1 0.1668 0.2772 -0.1286 11.00000 0.05 0.16 Q8 1 0.1590 0.4216 -0.1312 11.00000 0.05 0.16 Q9 1 0.2369 0.7407 -0.1200 11.00000 0.05 0.16 Q10 1 0.2203 0.5825 0.1544 11.00000 0.05 0.16 Q11 1 0.4998 0.3231 0.0868 11.00000 0.05 0.15 Q12 1 0.1979 0.6191 -0.0327 11.00000 0.05 0.15 Q13 1 0.1807 0.0989 0.1179 11.00000 0.05 0.15 Q14 1 0.2810 0.6170 0.1579 11.00000 0.05 0.15 Q15 1 0.2026 0.3522 -0.2377 11.00000 0.05 0.15 Q16 1 0.3450 0.7544 0.0263 11.00000 0.05 0.15 Q17 1 0.2008 0.1926 -0.0652 11.00000 0.05 0.15 Q18 1 0.5398 0.4031 0.1255 11.00000 0.05 0.14 Q19 1 0.1140 0.3480 -0.2828 11.00000 0.05 0.14 Q20 1 0.2820 0.7789 -0.0439 11.00000 0.05 0.14 ; _shelx_res_checksum 14738 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0.24480(4) 0.53331(6) 0.10404(4) 0.04621(19) Uani 1 1 d . S2 S 0.18282(5) 0.35229(6) -0.16365(4) 0.04936(19) Uani 1 1 d . F1 F 0.10287(12) -0.11242(15) 0.03515(12) 0.0820(5) Uani 1 1 d . O1 O -0.00375(11) 0.40387(17) -0.15497(12) 0.0608(5) Uani 1 1 d . O2 O 0.28020(12) 0.37406(18) -0.13970(14) 0.0684(5) Uani 1 1 d . O3 O 0.13329(15) 0.34183(17) -0.25814(11) 0.0695(5) Uani 1 1 d . N1 N 0.21814(12) 0.69069(18) -0.14278(12) 0.0413(4) Uani 1 1 d . N2 N 0.14162(12) 0.48708(16) -0.11689(11) 0.0387(4) Uani 1 1 d . C1 C 0.35886(17) 0.8248(3) 0.06794(19) 0.0584(7) Uani 1 1 d . H1 H 0.374973 0.800463 0.130149 0.070 Uiso 1 1 calc R C2 C 0.39260(19) 0.9409(3) 0.0388(2) 0.0723(8) Uani 1 1 d . H2 H 0.432201 0.995463 0.082073 0.087 Uiso 1 1 calc R C3 C 0.36846(19) 0.9781(3) -0.0541(2) 0.0691(8) Uani 1 1 d . H3 H 0.392214 1.057290 -0.071522 0.083 Uiso 1 1 calc R C4 C 0.31138(16) 0.9022(2) -0.11995(19) 0.0536(6) Uani 1 1 d . H4 H 0.295473 0.927896 -0.181879 0.064 Uiso 1 1 calc R C5 C 0.27744(14) 0.7844(2) -0.09150(15) 0.0412(5) Uani 1 1 d . C6 C 0.29994(14) 0.7447(2) 0.00158(15) 0.0426(5) Uani 1 1 d . C7 C 0.25193(14) 0.6215(2) 0.00580(14) 0.0389(5) Uani 1 1 d . C8 C 0.20356(14) 0.5936(2) -0.08311(14) 0.0368(5) Uani 1 1 d . C9 C 0.34640(15) 0.4330(2) 0.13423(14) 0.0421(5) Uani 1 1 d . C10 C 0.35106(18) 0.3408(2) 0.20360(16) 0.0536(6) Uani 1 1 d . H10 H 0.303185 0.335929 0.232680 0.064 Uiso 1 1 calc R C11 C 0.4257(2) 0.2557(3) 0.23056(18) 0.0667(7) Uani 1 1 d . H11 H 0.428061 0.194128 0.277853 0.080 Uiso 1 1 calc R C12 C 0.4957(2) 0.2612(3) 0.18850(19) 0.0739(8) Uani 1 1 d . H12 H 0.546214 0.203733 0.206560 0.089 Uiso 1 1 calc R C13 C 0.4911(2) 0.3521(4) 0.1193(2) 0.0923(11) Uani 1 1 d . H13 H 0.538894 0.355684 0.090144 0.111 Uiso 1 1 calc R C14 C 0.41711(19) 0.4388(3) 0.09161(19) 0.0709(8) Uani 1 1 d . H14 H 0.415300 0.500518 0.044522 0.085 Uiso 1 1 calc R C15 C 0.04669(16) 0.4951(2) -0.12212(15) 0.0429(5) Uani 1 1 d . C16 C 0.01514(16) 0.6204(2) -0.08521(18) 0.0525(6) Uani 1 1 d . H16A H 0.046303 0.629448 -0.020697 0.079 Uiso 1 1 calc GR H16B H -0.050553 0.616114 -0.092527 0.079 Uiso 1 1 calc GR H16C H 0.029344 0.696169 -0.118640 0.079 Uiso 1 1 calc GR C17 C 0.15693(16) 0.2137(2) -0.10353(15) 0.0432(5) Uani 1 1 d . C18 C 0.09404(19) 0.1204(2) -0.14874(18) 0.0618(7) Uani 1 1 d . H18 H 0.063579 0.132270 -0.210903 0.074 Uiso 1 1 calc R C19 C 0.0761(2) 0.0092(3) -0.1021(2) 0.0668(8) Uani 1 1 d . H19 H 0.034378 -0.055797 -0.132128 0.080 Uiso 1 1 calc R C20 C 0.12061(19) -0.0032(2) -0.01128(19) 0.0560(6) Uani 1 1 d . C21 C 0.1826(2) 0.0879(3) 0.03542(18) 0.0630(7) Uani 1 1 d . H21 H 0.211483 0.076201 0.097986 0.076 Uiso 1 1 calc R C22 C 0.20177(18) 0.1979(2) -0.01165(16) 0.0575(7) Uani 1 1 d . H22 H 0.244831 0.261170 0.018526 0.069 Uiso 1 1 calc R C23 C 0.18191(18) 0.6939(3) -0.24281(15) 0.0600(7) Uani 1 1 d . H23A H 0.232301 0.689101 -0.271519 0.090 Uiso 1 1 calc GR H23B H 0.148275 0.775859 -0.260661 0.090 Uiso 1 1 calc GR H23C H 0.141205 0.618992 -0.262366 0.090 Uiso 1 1 calc GR 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 0.0499(4) 0.0550(4) 0.0354(3) 0.0039(3) 0.0142(3) 0.0083(3) S2 0.0674(4) 0.0409(3) 0.0439(4) -0.0065(2) 0.0219(3) 0.0009(3) F1 0.1085(14) 0.0528(9) 0.0899(12) 0.0161(9) 0.0353(10) -0.0024(9) O1 0.0506(10) 0.0472(10) 0.0764(12) -0.0070(9) 0.0018(9) -0.0069(8) O2 0.0631(12) 0.0578(11) 0.0969(14) -0.0122(10) 0.0433(11) -0.0004(8) O3 0.1150(16) 0.0562(11) 0.0385(10) -0.0067(8) 0.0219(10) -0.0029(10) N1 0.0470(11) 0.0385(10) 0.0374(10) 0.0050(8) 0.0092(8) -0.0011(8) N2 0.0458(11) 0.0328(9) 0.0371(10) -0.0032(8) 0.0096(8) -0.0008(7) C1 0.0486(15) 0.0598(16) 0.0605(16) -0.0125(13) 0.0028(12) -0.0034(12) C2 0.0540(17) 0.0630(18) 0.095(2) -0.0241(17) 0.0106(16) -0.0191(13) C3 0.0593(17) 0.0533(16) 0.099(2) -0.0008(16) 0.0286(16) -0.0119(13) C4 0.0480(14) 0.0457(14) 0.0701(17) 0.0072(13) 0.0205(13) -0.0008(11) C5 0.0374(12) 0.0379(12) 0.0490(13) 0.0026(10) 0.0123(10) 0.0028(9) C6 0.0339(12) 0.0432(12) 0.0485(13) -0.0036(10) 0.0067(10) 0.0027(9) C7 0.0410(12) 0.0376(11) 0.0373(12) 0.0001(9) 0.0087(9) 0.0059(9) C8 0.0401(12) 0.0333(11) 0.0377(12) 0.0029(9) 0.0111(9) 0.0024(9) C9 0.0460(13) 0.0459(13) 0.0322(11) -0.0014(10) 0.0061(10) 0.0003(10) C10 0.0611(16) 0.0533(15) 0.0474(14) 0.0070(12) 0.0160(12) 0.0035(11) C11 0.082(2) 0.0609(17) 0.0510(15) 0.0134(13) 0.0062(14) 0.0166(14) C12 0.070(2) 0.087(2) 0.0579(17) 0.0054(16) 0.0048(15) 0.0322(16) C13 0.065(2) 0.136(3) 0.086(2) 0.032(2) 0.0368(17) 0.041(2) C14 0.0637(18) 0.094(2) 0.0619(17) 0.0301(16) 0.0286(14) 0.0236(15) C15 0.0468(13) 0.0390(12) 0.0388(12) 0.0048(10) 0.0040(10) -0.0007(10) C16 0.0475(14) 0.0460(14) 0.0634(16) -0.0024(12) 0.0135(12) 0.0035(10) C17 0.0540(14) 0.0330(12) 0.0416(12) -0.0054(10) 0.0108(10) 0.0041(10) C18 0.0757(19) 0.0453(14) 0.0519(15) -0.0010(12) -0.0058(13) -0.0014(12) C19 0.0714(18) 0.0426(14) 0.0749(19) -0.0023(14) -0.0014(15) -0.0105(12) C20 0.0689(17) 0.0377(13) 0.0648(17) 0.0027(12) 0.0236(14) 0.0047(12) C21 0.093(2) 0.0500(15) 0.0423(14) -0.0017(12) 0.0099(13) 0.0025(14) C22 0.0751(18) 0.0446(14) 0.0477(14) -0.0090(12) 0.0066(13) -0.0070(12) C23 0.0732(18) 0.0641(16) 0.0380(13) 0.0135(12) 0.0058(12) -0.0082(13) 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' F F 0.0171 0.0103 '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 C7 S1 C9 105.28(10) O2 S2 N2 103.40(10) O2 S2 C17 109.90(12) O3 S2 O2 119.80(12) O3 S2 N2 108.44(10) O3 S2 C17 109.05(11) N2 S2 C17 105.16(9) C5 N1 C23 124.90(18) C8 N1 C5 107.79(17) C8 N1 C23 127.26(19) C8 N2 S2 117.83(14) C15 N2 S2 119.37(14) C15 N2 C8 122.44(17) C2 C1 H1 120.9 C2 C1 C6 118.2(3) C6 C1 H1 120.9 C1 C2 H2 119.4 C1 C2 C3 121.2(2) C3 C2 H2 119.4 C2 C3 H3 119.1 C4 C3 C2 121.8(3) C4 C3 H3 119.1 C3 C4 H4 121.2 C3 C4 C5 117.5(2) C5 C4 H4 121.2 N1 C5 C4 129.6(2) N1 C5 C6 108.33(18) C4 C5 C6 122.1(2) C1 C6 C5 119.3(2) C1 C6 C7 133.7(2) C5 C6 C7 107.02(19) C6 C7 S1 127.77(17) C8 C7 S1 125.81(17) C8 C7 C6 106.07(18) N1 C8 N2 119.88(18) C7 C8 N1 110.79(18) C7 C8 N2 129.26(19) C10 C9 S1 116.16(17) C14 C9 S1 124.77(18) C14 C9 C10 119.0(2) C9 C10 H10 119.6 C9 C10 C11 120.8(2) C11 C10 H10 119.6 C10 C11 H11 119.9 C12 C11 C10 120.3(3) C12 C11 H11 119.9 C11 C12 H12 120.5 C11 C12 C13 119.1(3) C13 C12 H12 120.5 C12 C13 H13 119.2 C12 C13 C14 121.6(3) C14 C13 H13 119.2 C9 C14 C13 119.2(3) C9 C14 H14 120.4 C13 C14 H14 120.4 O1 C15 N2 119.9(2) O1 C15 C16 124.1(2) N2 C15 C16 116.08(19) C15 C16 H16A 109.5 C15 C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16B 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C18 C17 S2 119.96(18) C18 C17 C22 120.7(2) C22 C17 S2 119.36(18) C17 C18 H18 120.1 C17 C18 C19 119.9(2) C19 C18 H18 120.1 C18 C19 H19 120.9 C20 C19 C18 118.3(2) C20 C19 H19 120.9 F1 C20 C21 118.3(2) C19 C20 F1 118.5(2) C19 C20 C21 123.2(2) C20 C21 H21 120.7 C20 C21 C22 118.5(2) C22 C21 H21 120.7 C17 C22 C21 119.5(2) C17 C22 H22 120.3 C21 C22 H22 120.3 N1 C23 H23A 109.5 N1 C23 H23B 109.5 N1 C23 H23C 109.5 H23A C23 H23B 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C7 1.739(2) S1 C9 1.776(2) S2 O2 1.4221(19) S2 O3 1.4178(18) S2 N2 1.7024(17) S2 C17 1.746(2) F1 C20 1.354(3) O1 C15 1.202(3) N1 C5 1.376(3) N1 C8 1.372(3) N1 C23 1.452(3) N2 C8 1.413(3) N2 C15 1.403(3) C1 H1 0.9300 C1 C2 1.378(4) C1 C6 1.394(3) C2 H2 0.9300 C2 C3 1.392(4) C3 H3 0.9300 C3 C4 1.354(4) C4 H4 0.9300 C4 C5 1.389(3) C5 C6 1.401(3) C6 C7 1.432(3) C7 C8 1.366(3) C9 C10 1.374(3) C9 C14 1.370(3) C10 H10 0.9300 C10 C11 1.376(3) C11 H11 0.9300 C11 C12 1.355(4) C12 H12 0.9300 C12 C13 1.363(4) C13 H13 0.9300 C13 C14 1.380(4) C14 H14 0.9300 C15 C16 1.491(3) C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C17 C18 1.370(3) C17 C22 1.372(3) C18 H18 0.9300 C18 C19 1.372(4) C19 H19 0.9300 C19 C20 1.353(4) C20 C21 1.354(4) C21 H21 0.9300 C21 C22 1.373(3) C22 H22 0.9300 C23 H23A 0.9600 C23 H23B 0.9600 C23 H23C 0.9600