#------------------------------------------------------------------------------ #$Date: 2021-10-03 03:42:05 +0300 (Sun, 03 Oct 2021) $ #$Revision: 269454 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060994.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_7060994 loop_ _publ_author_name 'Maegawa, Rikuto' 'Kitagawa, Daichi' 'Hamatani, Shota' 'Kobatake, Seiya' _publ_section_title ; Rational design of photochromic diarylbenzene with both high photoreactivity and fast thermal back reactivity ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04047B _journal_year 2021 _chemical_formula_moiety 'C28 H22 F2 N2 S2' _chemical_formula_sum 'C28 H22 F2 N2 S2' _chemical_formula_weight 488.60 _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_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-08-24 deposited with the CCDC. 2021-09-13 downloaded from the CCDC. ; _cell_angle_alpha 74.717(4) _cell_angle_beta 83.855(2) _cell_angle_gamma 89.388(2) _cell_formula_units_Z 2 _cell_length_a 7.83940(10) _cell_length_b 12.4027(5) _cell_length_c 12.7386(6) _cell_measurement_reflns_used 8384 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.4600 _cell_measurement_theta_min 2.0280 _cell_volume 1187.71(8) _computing_cell_refinement 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 7.32 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.864 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_Laue_measured_fraction_full 0.977 _diffrn_reflns_Laue_measured_fraction_max 0.864 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 12614 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.864 _diffrn_reflns_theta_full 25.241 _diffrn_reflns_theta_max 30.131 _diffrn_reflns_theta_min 2.679 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.366 _exptl_crystal_description Block _exptl_crystal_F_000 508 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.450 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.369 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 6039 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0375 _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^)+(0.0451P)^2^+0.5522P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0929 _refine_ls_wR_factor_ref 0.0963 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5520 _reflns_number_total 6039 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04047b4.cif _cod_data_source_block DAB_Et _cod_database_code 7060994 _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. ; _shelx_estimated_absorpt_t_min 0.892 _shelx_estimated_absorpt_t_max 0.975 _shelx_res_file ; DAB_Et.res created by SHELXL-2014/7 TITL REM Yadorkari-X generated CELL 0.71070 7.8394 12.4027 12.7386 74.7170 83.8550 89.3880 ZERR 2.0 0.0001 0.0005 0.0006 0.0040 0.0020 0.0020 LATT 1 REM SPGR P-1 triclinic SFAC C H F N S UNIT 56 44 4 4 4 SIZE 0.45 0.45 0.10 TEMP -123.0 L.S. 20 FMAP 2 PLAN -20 ACTA CONF WGHT 0.045100 0.552200 FVAR 7.06045 F1 3 -0.183636 0.989991 0.887003 11.00000 0.04444 0.02282 = 0.02865 -0.01297 -0.00438 0.01092 F2 3 -0.083203 0.819539 1.046245 11.00000 0.04185 0.03145 = 0.01901 -0.01155 -0.00402 0.00910 C1 1 0.422857 0.739803 0.502691 11.00000 0.02179 0.03099 = 0.03377 -0.00589 0.00305 0.00279 AFIX 137 H1 2 0.409608 0.711324 0.439143 11.00000 -1.50000 H2 2 0.526234 0.708739 0.535458 11.00000 -1.50000 H3 2 0.433298 0.821538 0.479385 11.00000 -1.50000 AFIX 0 C2 1 0.266222 0.705240 0.586932 11.00000 0.02040 0.02101 = 0.02491 -0.00413 -0.00148 0.00316 AFIX 23 H4 2 0.247772 0.623452 0.602549 11.00000 -1.20000 H5 2 0.289881 0.721912 0.655884 11.00000 -1.20000 AFIX 0 C3 1 0.104489 0.762941 0.550787 11.00000 0.02179 0.01697 = 0.01936 -0.00465 -0.00088 0.00057 C4 1 -0.033469 0.796959 0.609849 11.00000 0.02067 0.01578 = 0.01803 -0.00464 -0.00180 0.00089 C5 1 -0.117229 0.866206 0.443790 11.00000 0.02086 0.01788 = 0.01940 -0.00540 -0.00120 0.00124 C6 1 -0.219197 0.930410 0.358674 11.00000 0.01986 0.01739 = 0.01871 -0.00387 -0.00143 -0.00085 C7 1 -0.337718 1.006596 0.385851 11.00000 0.02584 0.02406 = 0.02155 -0.00714 -0.00128 0.00430 AFIX 43 H6 2 -0.351576 1.015255 0.458169 11.00000 -1.20000 AFIX 0 C8 1 -0.435138 1.069581 0.307407 11.00000 0.02702 0.02662 = 0.02980 -0.00736 -0.00437 0.00717 AFIX 43 H7 2 -0.517010 1.120105 0.326545 11.00000 -1.20000 AFIX 0 C9 1 -0.412910 1.058729 0.201014 11.00000 0.02911 0.02790 = 0.02589 -0.00263 -0.00863 0.00375 AFIX 43 H8 2 -0.478971 1.102292 0.147353 11.00000 -1.20000 AFIX 0 C10 1 -0.294359 0.984354 0.173001 11.00000 0.03353 0.03217 = 0.02064 -0.00792 -0.00534 0.00243 AFIX 43 H9 2 -0.278791 0.977460 0.100078 11.00000 -1.20000 AFIX 0 C11 1 -0.198248 0.919850 0.251646 11.00000 0.02787 0.02411 = 0.02084 -0.00821 -0.00294 0.00293 AFIX 43 H10 2 -0.118079 0.868437 0.232407 11.00000 -1.20000 AFIX 0 C12 1 -0.055919 0.790645 0.728567 11.00000 0.01876 0.01777 = 0.01846 -0.00541 -0.00118 0.00062 C13 1 -0.117662 0.887994 0.755522 11.00000 0.02324 0.01840 = 0.02088 -0.00473 -0.00237 0.00288 AFIX 43 H11 2 -0.152272 0.949027 0.699913 11.00000 -1.20000 AFIX 0 C14 1 -0.128176 0.895291 0.861643 11.00000 0.02426 0.01752 = 0.02484 -0.00913 -0.00169 0.00406 C15 1 -0.077886 0.807428 0.943515 11.00000 0.02340 0.02409 = 0.01745 -0.00731 -0.00140 0.00189 C16 1 -0.023758 0.709252 0.920877 11.00000 0.02380 0.02076 = 0.01825 -0.00425 -0.00250 0.00283 AFIX 43 H12 2 0.007812 0.648606 0.977995 11.00000 -1.20000 AFIX 0 C17 1 -0.015177 0.698695 0.813352 11.00000 0.01833 0.01725 = 0.01981 -0.00534 -0.00098 0.00079 C18 1 -0.219060 0.523221 0.586205 11.00000 0.03973 0.03880 = 0.04406 -0.01905 -0.02236 0.01070 AFIX 137 H13 2 -0.145190 0.580277 0.533642 11.00000 -1.50000 H14 2 -0.335911 0.528747 0.564805 11.00000 -1.50000 H15 2 -0.174650 0.448890 0.586959 11.00000 -1.50000 AFIX 0 C19 1 -0.221284 0.541497 0.700084 11.00000 0.02031 0.02028 = 0.03354 -0.00622 -0.00720 0.00178 AFIX 23 H16 2 -0.259160 0.618513 0.697286 11.00000 -1.20000 H17 2 -0.306552 0.489253 0.750792 11.00000 -1.20000 AFIX 0 C20 1 -0.049964 0.524671 0.745224 11.00000 0.02074 0.01628 = 0.02185 -0.00265 -0.00243 0.00141 C21 1 0.036371 0.588313 0.796353 11.00000 0.02036 0.01616 = 0.01823 -0.00287 -0.00082 0.00083 C22 1 0.216837 0.446747 0.816762 11.00000 0.02134 0.01775 = 0.01989 -0.00412 -0.00279 0.00051 C23 1 0.366211 0.378477 0.850540 11.00000 0.02045 0.01582 = 0.02521 -0.00325 -0.00253 -0.00030 C24 1 0.441264 0.388774 0.941853 11.00000 0.02741 0.02311 = 0.02928 -0.00818 -0.00580 0.00314 AFIX 43 H18 2 0.394855 0.438966 0.981870 11.00000 -1.20000 AFIX 0 C25 1 0.583729 0.326085 0.974906 11.00000 0.02973 0.03128 = 0.03431 -0.00582 -0.01242 0.00439 AFIX 43 H19 2 0.635183 0.334138 1.036695 11.00000 -1.20000 AFIX 0 C26 1 0.650519 0.251480 0.916967 11.00000 0.02553 0.02657 = 0.04394 -0.00350 -0.00757 0.00744 AFIX 43 H20 2 0.747513 0.208428 0.939426 11.00000 -1.20000 AFIX 0 C27 1 0.575921 0.239994 0.826880 11.00000 0.02761 0.02471 = 0.04122 -0.01056 -0.00048 0.00648 AFIX 43 H21 2 0.621396 0.188657 0.787930 11.00000 -1.20000 AFIX 0 C28 1 0.434061 0.303486 0.792870 11.00000 0.02493 0.02354 = 0.02979 -0.00952 -0.00338 0.00237 AFIX 43 H22 2 0.383701 0.295729 0.730596 11.00000 -1.20000 AFIX 0 S1 5 0.074827 0.804307 0.413061 11.00000 0.02335 0.02219 = 0.01831 -0.00530 0.00027 0.00482 N1 4 -0.156716 0.855765 0.548496 11.00000 0.02086 0.01922 = 0.01906 -0.00463 -0.00244 0.00267 S2 5 0.064159 0.404189 0.745960 11.00000 0.02440 0.01703 = 0.02849 -0.00793 -0.00767 0.00235 N2 4 0.184739 0.542802 0.838680 11.00000 0.02169 0.01810 = 0.01910 -0.00459 -0.00324 0.00207 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0375 for 5520 Fo > 4sig(Fo) and 0.0411 for all 6039 data REM 309 parameters refined using 0 restraints END WGHT 0.0451 0.5534 REM Highest difference peak 0.369, deepest hole -0.318, 1-sigma level 0.051 Q1 1 -0.1373 0.5382 0.7200 11.00000 0.05 0.37 Q2 1 -0.0417 0.7920 0.6634 11.00000 0.05 0.36 Q3 1 0.0014 0.6472 0.8046 11.00000 0.05 0.36 Q4 1 -0.0645 0.8574 0.8981 11.00000 0.05 0.35 Q5 1 -0.1652 0.8964 0.3997 11.00000 0.05 0.34 Q6 1 -0.2644 0.9806 0.3643 11.00000 0.05 0.33 Q7 1 -0.0865 0.8973 0.8020 11.00000 0.05 0.30 Q8 1 -0.2021 0.9315 0.3008 11.00000 0.05 0.30 Q9 1 -0.0785 0.8390 0.7435 11.00000 0.05 0.30 Q10 1 0.0184 0.7607 0.5918 11.00000 0.05 0.29 Q11 1 -0.0447 0.7671 0.9291 11.00000 0.05 0.28 Q12 1 0.1456 0.4215 0.7948 11.00000 0.05 0.28 Q13 1 -0.2917 0.9578 0.3757 11.00000 0.05 0.28 Q14 1 -0.3927 1.0364 0.3427 11.00000 0.05 0.28 Q15 1 0.4099 0.3415 0.8286 11.00000 0.05 0.27 Q16 1 -0.1641 0.8778 0.8199 11.00000 0.05 0.27 Q17 1 -0.0938 0.8253 0.5821 11.00000 0.05 0.27 Q18 1 -0.0219 0.5571 0.7771 11.00000 0.05 0.27 Q19 1 0.0045 0.7056 0.8590 11.00000 0.05 0.26 Q20 1 0.1731 0.7329 0.5776 11.00000 0.05 0.25 ; _shelx_res_checksum 23704 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_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.18364(11) 0.98999(7) 0.88700(7) 0.03084(19) Uani 1 1 d . . . . . F2 F -0.08320(11) 0.81954(7) 1.04625(7) 0.02985(19) Uani 1 1 d . . . . . C1 C 0.42286(17) 0.73980(13) 0.50269(13) 0.0298(3) Uani 1 1 d . . . . . H1 H 0.4096 0.7113 0.4391 0.045 Uiso 1 1 calc R U . . . H2 H 0.5262 0.7087 0.5355 0.045 Uiso 1 1 calc R U . . . H3 H 0.4333 0.8215 0.4794 0.045 Uiso 1 1 calc R U . . . C2 C 0.26622(15) 0.70524(11) 0.58693(11) 0.0226(2) Uani 1 1 d . . . . . H4 H 0.2478 0.6235 0.6025 0.027 Uiso 1 1 calc R U . . . H5 H 0.2899 0.7219 0.6559 0.027 Uiso 1 1 calc R U . . . C3 C 0.10449(15) 0.76294(10) 0.55079(10) 0.0195(2) Uani 1 1 d . . . . . C4 C -0.03347(15) 0.79696(10) 0.60985(10) 0.0182(2) Uani 1 1 d . . . . . C5 C -0.11723(15) 0.86621(10) 0.44379(10) 0.0194(2) Uani 1 1 d . . . . . C6 C -0.21920(15) 0.93041(10) 0.35867(10) 0.0189(2) Uani 1 1 d . . . . . C7 C -0.33772(16) 1.00660(11) 0.38585(11) 0.0237(3) Uani 1 1 d . . . . . H6 H -0.3516 1.0153 0.4582 0.028 Uiso 1 1 calc R U . . . C8 C -0.43514(17) 1.06958(12) 0.30741(12) 0.0278(3) Uani 1 1 d . . . . . H7 H -0.5170 1.1201 0.3265 0.033 Uiso 1 1 calc R U . . . C9 C -0.41291(18) 1.05873(12) 0.20101(12) 0.0281(3) Uani 1 1 d . . . . . H8 H -0.4790 1.1023 0.1474 0.034 Uiso 1 1 calc R U . . . C10 C -0.29436(18) 0.98435(13) 0.17300(12) 0.0284(3) Uani 1 1 d . . . . . H9 H -0.2788 0.9775 0.1001 0.034 Uiso 1 1 calc R U . . . C11 C -0.19825(17) 0.91985(11) 0.25165(11) 0.0238(3) Uani 1 1 d . . . . . H10 H -0.1181 0.8684 0.2324 0.029 Uiso 1 1 calc R U . . . C12 C -0.05592(15) 0.79065(10) 0.72857(10) 0.0183(2) Uani 1 1 d . . . . . C13 C -0.11766(15) 0.88799(10) 0.75552(10) 0.0209(2) Uani 1 1 d . . . . . H11 H -0.1523 0.9490 0.6999 0.025 Uiso 1 1 calc R U . . . C14 C -0.12818(16) 0.89529(11) 0.86164(11) 0.0216(2) Uani 1 1 d . . . . . C15 C -0.07789(16) 0.80743(11) 0.94351(10) 0.0214(2) Uani 1 1 d . . . . . C16 C -0.02376(16) 0.70925(11) 0.92088(10) 0.0211(2) Uani 1 1 d . . . . . H12 H 0.0078 0.6486 0.9780 0.025 Uiso 1 1 calc R U . . . C17 C -0.01518(15) 0.69870(10) 0.81335(10) 0.0185(2) Uani 1 1 d . . . . . C18 C -0.2191(2) 0.52322(15) 0.58620(15) 0.0381(4) Uani 1 1 d . . . . . H13 H -0.1452 0.5803 0.5336 0.057 Uiso 1 1 calc R U . . . H14 H -0.3359 0.5287 0.5648 0.057 Uiso 1 1 calc R U . . . H15 H -0.1746 0.4489 0.5870 0.057 Uiso 1 1 calc R U . . . C19 C -0.22128(16) 0.54150(11) 0.70008(12) 0.0246(3) Uani 1 1 d . . . . . H16 H -0.2592 0.6185 0.6973 0.029 Uiso 1 1 calc R U . . . H17 H -0.3066 0.4893 0.7508 0.029 Uiso 1 1 calc R U . . . C20 C -0.04996(15) 0.52467(10) 0.74522(10) 0.0201(2) Uani 1 1 d . . . . . C21 C 0.03637(15) 0.58831(10) 0.79635(10) 0.0187(2) Uani 1 1 d . . . . . C22 C 0.21684(15) 0.44675(10) 0.81676(10) 0.0198(2) Uani 1 1 d . . . . . C23 C 0.36621(15) 0.37848(10) 0.85054(11) 0.0209(2) Uani 1 1 d . . . . . C24 C 0.44126(17) 0.38877(11) 0.94185(12) 0.0262(3) Uani 1 1 d . . . . . H18 H 0.3949 0.4390 0.9819 0.031 Uiso 1 1 calc R U . . . C25 C 0.58373(18) 0.32609(13) 0.97491(13) 0.0317(3) Uani 1 1 d . . . . . H19 H 0.6352 0.3341 1.0367 0.038 Uiso 1 1 calc R U . . . C26 C 0.65052(18) 0.25148(13) 0.91697(14) 0.0329(3) Uani 1 1 d . . . . . H20 H 0.7475 0.2084 0.9394 0.039 Uiso 1 1 calc R U . . . C27 C 0.57592(18) 0.23999(12) 0.82688(13) 0.0311(3) Uani 1 1 d . . . . . H21 H 0.6214 0.1887 0.7879 0.037 Uiso 1 1 calc R U . . . C28 C 0.43406(17) 0.30349(11) 0.79287(12) 0.0256(3) Uani 1 1 d . . . . . H22 H 0.3837 0.2957 0.7306 0.031 Uiso 1 1 calc R U . . . S1 S 0.07483(4) 0.80431(3) 0.41306(3) 0.02151(8) Uani 1 1 d . . . . . N1 N -0.15672(13) 0.85576(9) 0.54850(9) 0.0198(2) Uani 1 1 d . . . . . S2 S 0.06416(4) 0.40419(3) 0.74596(3) 0.02260(8) Uani 1 1 d . . . . . N2 N 0.18474(13) 0.54280(9) 0.83868(9) 0.0196(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 F1 0.0444(5) 0.0228(4) 0.0286(4) -0.0130(3) -0.0044(4) 0.0109(3) F2 0.0419(4) 0.0315(4) 0.0190(4) -0.0115(3) -0.0040(3) 0.0091(4) C1 0.0218(6) 0.0310(7) 0.0338(8) -0.0059(6) 0.0030(5) 0.0028(5) C2 0.0204(5) 0.0210(6) 0.0249(6) -0.0041(5) -0.0015(5) 0.0032(4) C3 0.0218(5) 0.0170(5) 0.0194(6) -0.0046(4) -0.0009(4) 0.0006(4) C4 0.0207(5) 0.0158(5) 0.0180(5) -0.0046(4) -0.0018(4) 0.0009(4) C5 0.0209(5) 0.0179(5) 0.0194(6) -0.0054(4) -0.0012(4) 0.0012(4) C6 0.0199(5) 0.0174(5) 0.0187(6) -0.0039(4) -0.0014(4) -0.0008(4) C7 0.0258(6) 0.0241(6) 0.0216(6) -0.0071(5) -0.0013(5) 0.0043(5) C8 0.0270(6) 0.0266(7) 0.0298(7) -0.0074(5) -0.0044(5) 0.0072(5) C9 0.0291(6) 0.0279(7) 0.0259(7) -0.0026(5) -0.0086(5) 0.0037(5) C10 0.0335(7) 0.0322(7) 0.0206(6) -0.0079(5) -0.0053(5) 0.0024(6) C11 0.0279(6) 0.0241(6) 0.0208(6) -0.0082(5) -0.0029(5) 0.0029(5) C12 0.0188(5) 0.0178(5) 0.0185(6) -0.0054(4) -0.0012(4) 0.0006(4) C13 0.0232(5) 0.0184(6) 0.0209(6) -0.0047(5) -0.0024(5) 0.0029(4) C14 0.0243(5) 0.0175(6) 0.0248(6) -0.0091(5) -0.0017(5) 0.0041(4) C15 0.0234(5) 0.0241(6) 0.0174(6) -0.0073(5) -0.0014(4) 0.0019(5) C16 0.0238(5) 0.0208(6) 0.0182(6) -0.0042(5) -0.0025(4) 0.0028(4) C17 0.0183(5) 0.0173(5) 0.0198(6) -0.0053(4) -0.0010(4) 0.0008(4) C18 0.0397(8) 0.0388(9) 0.0441(9) -0.0191(7) -0.0224(7) 0.0107(7) C19 0.0203(5) 0.0203(6) 0.0335(7) -0.0062(5) -0.0072(5) 0.0018(4) C20 0.0207(5) 0.0163(5) 0.0218(6) -0.0027(4) -0.0024(4) 0.0014(4) C21 0.0204(5) 0.0162(5) 0.0182(6) -0.0029(4) -0.0008(4) 0.0008(4) C22 0.0213(5) 0.0177(6) 0.0199(6) -0.0041(4) -0.0028(4) 0.0005(4) C23 0.0204(5) 0.0158(5) 0.0252(6) -0.0033(5) -0.0025(5) -0.0003(4) C24 0.0274(6) 0.0231(6) 0.0293(7) -0.0082(5) -0.0058(5) 0.0031(5) C25 0.0297(6) 0.0313(7) 0.0343(8) -0.0058(6) -0.0124(6) 0.0044(6) C26 0.0255(6) 0.0266(7) 0.0439(9) -0.0035(6) -0.0076(6) 0.0074(5) C27 0.0276(6) 0.0247(7) 0.0412(8) -0.0106(6) -0.0005(6) 0.0065(5) C28 0.0249(6) 0.0235(6) 0.0298(7) -0.0095(5) -0.0034(5) 0.0024(5) S1 0.02335(14) 0.02219(16) 0.01831(15) -0.00530(12) 0.00027(11) 0.00482(11) N1 0.0209(4) 0.0192(5) 0.0191(5) -0.0046(4) -0.0024(4) 0.0027(4) S2 0.02440(15) 0.01703(15) 0.02849(17) -0.00793(12) -0.00767(12) 0.00235(11) N2 0.0217(5) 0.0181(5) 0.0191(5) -0.0046(4) -0.0032(4) 0.0021(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' 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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C2 C1 113.66(11) . . ? C4 C3 C2 130.82(11) . . ? C4 C3 S1 108.76(9) . . ? C2 C3 S1 120.34(9) . . ? C3 C4 N1 115.50(11) . . ? C3 C4 C12 127.98(11) . . ? N1 C4 C12 116.06(10) . . ? N1 C5 C6 123.56(11) . . ? N1 C5 S1 113.79(9) . . ? C6 C5 S1 122.55(9) . . ? C11 C6 C7 119.25(11) . . ? C11 C6 C5 122.18(11) . . ? C7 C6 C5 118.54(11) . . ? C8 C7 C6 120.23(12) . . ? C9 C8 C7 120.06(12) . . ? C10 C9 C8 120.11(12) . . ? C9 C10 C11 120.07(13) . . ? C10 C11 C6 120.26(12) . . ? C13 C12 C17 118.77(11) . . ? C13 C12 C4 115.43(11) . . ? C17 C12 C4 125.76(11) . . ? C14 C13 C12 120.40(11) . . ? F1 C14 C13 120.33(11) . . ? F1 C14 C15 119.08(11) . . ? C13 C14 C15 120.57(11) . . ? F2 C15 C16 120.61(11) . . ? F2 C15 C14 118.85(11) . . ? C16 C15 C14 120.55(12) . . ? C15 C16 C17 120.01(11) . . ? C16 C17 C12 119.49(11) . . ? C16 C17 C21 116.83(11) . . ? C12 C17 C21 123.67(11) . . ? C20 C19 C18 113.83(11) . . ? C21 C20 C19 130.65(11) . . ? C21 C20 S2 108.72(9) . . ? C19 C20 S2 120.48(10) . . ? C20 C21 N2 116.01(11) . . ? C20 C21 C17 126.82(11) . . ? N2 C21 C17 117.15(10) . . ? N2 C22 C23 123.71(11) . . ? N2 C22 S2 114.04(9) . . ? C23 C22 S2 122.24(9) . . ? C24 C23 C28 119.37(12) . . ? C24 C23 C22 119.34(12) . . ? C28 C23 C22 121.29(12) . . ? C25 C24 C23 120.53(13) . . ? C24 C25 C26 119.72(14) . . ? C27 C26 C25 120.13(13) . . ? C26 C27 C28 120.31(13) . . ? C27 C28 C23 119.93(13) . . ? C3 S1 C5 90.34(6) . . ? C5 N1 C4 111.59(10) . . ? C20 S2 C22 90.19(6) . . ? C22 N2 C21 110.99(10) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C14 1.3535(14) . ? F2 C15 1.3523(14) . ? C1 C2 1.5264(18) . ? C2 C3 1.5045(16) . ? C3 C4 1.3774(16) . ? C3 S1 1.7337(13) . ? C4 N1 1.3865(15) . ? C4 C12 1.4849(17) . ? C5 N1 1.3088(16) . ? C5 C6 1.4716(16) . ? C5 S1 1.7370(12) . ? C6 C11 1.3960(17) . ? C6 C7 1.4003(17) . ? C7 C8 1.3897(18) . ? C8 C9 1.389(2) . ? C9 C10 1.388(2) . ? C10 C11 1.3920(19) . ? C12 C13 1.4073(16) . ? C12 C17 1.4092(16) . ? C13 C14 1.3722(18) . ? C14 C15 1.3822(18) . ? C15 C16 1.3761(17) . ? C16 C17 1.4044(17) . ? C17 C21 1.4867(16) . ? C18 C19 1.524(2) . ? C19 C20 1.5080(17) . ? C20 C21 1.3719(18) . ? C20 S2 1.7319(12) . ? C21 N2 1.3864(15) . ? C22 N2 1.3094(16) . ? C22 C23 1.4724(16) . ? C22 S2 1.7379(13) . ? C23 C24 1.3935(19) . ? C23 C28 1.3977(18) . ? C24 C25 1.3924(18) . ? C25 C26 1.394(2) . ? C26 C27 1.382(2) . ? C27 C28 1.3961(18) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 -146.39(14) . . . . ? C1 C2 C3 S1 29.98(16) . . . . ? C2 C3 C4 N1 175.40(12) . . . . ? S1 C3 C4 N1 -1.29(14) . . . . ? C2 C3 C4 C12 3.6(2) . . . . ? S1 C3 C4 C12 -173.13(10) . . . . ? N1 C5 C6 C11 -165.07(12) . . . . ? S1 C5 C6 C11 19.01(17) . . . . ? N1 C5 C6 C7 16.64(19) . . . . ? S1 C5 C6 C7 -159.28(10) . . . . ? C11 C6 C7 C8 1.0(2) . . . . ? C5 C6 C7 C8 179.35(12) . . . . ? C6 C7 C8 C9 -1.2(2) . . . . ? C7 C8 C9 C10 0.5(2) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? C9 C10 C11 C6 -0.7(2) . . . . ? C7 C6 C11 C10 -0.1(2) . . . . ? C5 C6 C11 C10 -178.34(13) . . . . ? C3 C4 C12 C13 134.19(13) . . . . ? N1 C4 C12 C13 -37.61(15) . . . . ? C3 C4 C12 C17 -43.36(19) . . . . ? N1 C4 C12 C17 144.84(12) . . . . ? C17 C12 C13 C14 3.81(18) . . . . ? C4 C12 C13 C14 -173.92(11) . . . . ? C12 C13 C14 F1 178.39(11) . . . . ? C12 C13 C14 C15 0.20(19) . . . . ? F1 C14 C15 F2 -1.01(18) . . . . ? C13 C14 C15 F2 177.20(11) . . . . ? F1 C14 C15 C16 178.83(12) . . . . ? C13 C14 C15 C16 -3.0(2) . . . . ? F2 C15 C16 C17 -178.56(11) . . . . ? C14 C15 C16 C17 1.60(19) . . . . ? C15 C16 C17 C12 2.45(18) . . . . ? C15 C16 C17 C21 -177.12(11) . . . . ? C13 C12 C17 C16 -5.09(17) . . . . ? C4 C12 C17 C16 172.38(11) . . . . ? C13 C12 C17 C21 174.46(11) . . . . ? C4 C12 C17 C21 -8.07(18) . . . . ? C18 C19 C20 C21 133.96(15) . . . . ? C18 C19 C20 S2 -50.95(16) . . . . ? C19 C20 C21 N2 173.36(13) . . . . ? S2 C20 C21 N2 -2.17(14) . . . . ? C19 C20 C21 C17 -4.9(2) . . . . ? S2 C20 C21 C17 179.57(10) . . . . ? C16 C17 C21 C20 127.15(14) . . . . ? C12 C17 C21 C20 -52.41(18) . . . . ? C16 C17 C21 N2 -51.09(15) . . . . ? C12 C17 C21 N2 129.35(12) . . . . ? N2 C22 C23 C24 25.62(19) . . . . ? S2 C22 C23 C24 -152.97(11) . . . . ? N2 C22 C23 C28 -154.44(13) . . . . ? S2 C22 C23 C28 26.96(17) . . . . ? C28 C23 C24 C25 0.7(2) . . . . ? C22 C23 C24 C25 -179.32(13) . . . . ? C23 C24 C25 C26 -0.8(2) . . . . ? C24 C25 C26 C27 0.2(2) . . . . ? C25 C26 C27 C28 0.4(2) . . . . ? C26 C27 C28 C23 -0.5(2) . . . . ? C24 C23 C28 C27 -0.1(2) . . . . ? C22 C23 C28 C27 179.94(12) . . . . ? C4 C3 S1 C5 1.04(10) . . . . ? C2 C3 S1 C5 -176.06(11) . . . . ? N1 C5 S1 C3 -0.62(10) . . . . ? C6 C5 S1 C3 175.66(11) . . . . ? C6 C5 N1 C4 -176.24(11) . . . . ? S1 C5 N1 C4 0.00(14) . . . . ? C3 C4 N1 C5 0.86(15) . . . . ? C12 C4 N1 C5 173.70(11) . . . . ? C21 C20 S2 C22 1.00(10) . . . . ? C19 C20 S2 C22 -175.07(11) . . . . ? N2 C22 S2 C20 0.36(10) . . . . ? C23 C22 S2 C20 179.08(11) . . . . ? C23 C22 N2 C21 179.69(11) . . . . ? S2 C22 N2 C21 -1.61(14) . . . . ? C20 C21 N2 C22 2.49(16) . . . . ? C17 C21 N2 C22 -179.07(11) . . . . ?