#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:32:45 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270489 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060995.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_7060995 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_issue 40 _journal_name_full 'New Journal of Chemistry' _journal_page_first 18969 _journal_page_last 18975 _journal_paper_doi 10.1039/D1NJ04047B _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C30 H26 F2 N2 S2' _chemical_formula_sum 'C30 H26 F2 N2 S2' _chemical_formula_weight 516.65 _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_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 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 90 _cell_angle_beta 99.908(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0824(5) _cell_length_b 19.6538(9) _cell_length_c 15.2420(8) _cell_measurement_reflns_used 5763 _cell_measurement_temperature 150.1500 _cell_measurement_theta_max 27.4816 _cell_measurement_theta_min 2.0725 _cell_volume 2680.2(2) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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)' _computing_structure_solution ; ???? ; _diffrn_ambient_temperature 150.1500 _diffrn_detector_area_resol_mean 14.6306 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type ; Mercury70 (2x2 bin mode) ; _diffrn_measurement_method dtprofit.ref _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 26264 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.475 _diffrn_reflns_theta_min 2.072 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.280 _exptl_crystal_description Block _exptl_crystal_F_000 1080 _exptl_crystal_size_max 0.4700 _exptl_crystal_size_mid 0.2200 _exptl_crystal_size_min 0.1400 _refine_diff_density_max 0.264 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 329 _refine_ls_number_reflns 6090 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.120 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0485 _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^)+(0.0448P)^2^+1.1811P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1095 _refine_ls_wR_factor_ref 0.1152 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5445 _reflns_number_total 6090 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04047b4.cif _cod_data_source_block DAB_iPr _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7060994--7060995.cif. ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7060995 _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 0.898 _shelx_estimated_absorpt_t_max 0.968 _shelx_res_file ; DAB_iPr.res created by SHELXL-2014/7 TITL REM Yadorkari-X generated CELL 0.71075 9.0824 19.6538 15.2420 90.0000 99.9084 90.0000 ZERR 4.0 0.0005 0.0009 0.0008 0.0000 0.0020 0.0000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z REM SPGR P21/c monoclinic SFAC C H F N S UNIT 120 104 8 8 8 SIZE 0.47 0.22 0.14 TEMP -122.8 L.S. 20 FMAP 2 PLAN -20 ACTA CONF WGHT 0.044800 1.181100 FVAR 3.26256 F1 3 0.120479 0.052425 0.533930 11.00000 0.05487 0.02220 = 0.04552 0.00967 0.00340 0.00426 F2 3 0.030997 0.048978 0.355253 11.00000 0.06715 0.02111 = 0.04609 -0.00606 -0.00137 0.00049 S1 5 0.051176 0.409503 0.613010 11.00000 0.03302 0.02760 = 0.02983 -0.00329 0.00531 0.00356 S2 5 0.030981 0.400256 0.248088 11.00000 0.03144 0.02608 = 0.02614 0.00295 0.00374 -0.00409 C1 1 -0.178874 0.346912 0.491864 11.00000 0.02780 0.02879 = 0.03681 -0.00018 0.00587 0.00098 AFIX 13 H13 2 -0.194677 0.306771 0.451009 11.00000 -1.20000 AFIX 0 C2 1 -0.286889 0.340706 0.558535 11.00000 0.03637 0.06185 = 0.05853 0.01616 0.01569 -0.00088 AFIX 137 H14 2 -0.260525 0.300664 0.596288 11.00000 -1.50000 H15 2 -0.389312 0.335886 0.526106 11.00000 -1.50000 H16 2 -0.279837 0.381605 0.595804 11.00000 -1.50000 AFIX 0 C3 1 -0.212552 0.411021 0.435864 11.00000 0.03339 0.03582 = 0.04121 0.00523 0.00339 0.00401 AFIX 137 H17 2 -0.204085 0.450902 0.475005 11.00000 -1.50000 H18 2 -0.314227 0.408375 0.401768 11.00000 -1.50000 H19 2 -0.141012 0.415035 0.394787 11.00000 -1.50000 AFIX 0 C4 1 -0.019179 0.345623 0.539535 11.00000 0.03128 0.02432 = 0.02570 0.00206 0.00606 0.00046 C5 1 0.088972 0.297603 0.538816 11.00000 0.03074 0.02354 = 0.02278 0.00274 0.00415 0.00038 C6 1 0.220738 0.366660 0.637470 11.00000 0.03253 0.02827 = 0.02342 0.00075 0.00478 0.00254 C7 1 0.351123 0.395230 0.696710 11.00000 0.03546 0.03243 = 0.02267 -0.00034 0.00481 0.00062 C8 1 0.480298 0.356165 0.716863 11.00000 0.03903 0.04464 = 0.04178 -0.01072 0.00052 0.00724 AFIX 43 H1 2 0.480359 0.310629 0.695963 11.00000 -1.20000 AFIX 0 C9 1 0.608662 0.382966 0.767034 11.00000 0.03624 0.06832 = 0.04413 -0.01388 -0.00025 0.00775 AFIX 43 H2 2 0.695966 0.355712 0.780844 11.00000 -1.20000 AFIX 0 C10 1 0.609973 0.449479 0.797132 11.00000 0.03960 0.06695 = 0.03270 -0.01125 0.00279 -0.01080 AFIX 43 H3 2 0.699398 0.468582 0.829164 11.00000 -1.20000 AFIX 0 C11 1 0.481368 0.487861 0.780525 11.00000 0.05098 0.04310 = 0.03634 -0.00917 0.00330 -0.00824 AFIX 43 H4 2 0.481173 0.532904 0.803119 11.00000 -1.20000 AFIX 0 C12 1 0.352052 0.460972 0.730902 11.00000 0.04308 0.03366 = 0.03340 -0.00351 0.00107 0.00107 AFIX 43 H5 2 0.263485 0.487603 0.720169 11.00000 -1.20000 AFIX 0 C13 1 0.075088 0.233231 0.486335 11.00000 0.02573 0.02352 = 0.02970 0.00130 0.00438 0.00135 C14 1 0.104287 0.172268 0.533584 11.00000 0.02974 0.02744 = 0.02837 0.00285 0.00473 0.00064 AFIX 43 H6 2 0.133351 0.173002 0.596505 11.00000 -1.20000 AFIX 0 C15 1 0.090751 0.111213 0.488575 11.00000 0.03102 0.02184 = 0.03795 0.00830 0.00481 0.00221 C16 1 0.046621 0.109446 0.397656 11.00000 0.03653 0.02043 = 0.03962 -0.00305 0.00414 0.00077 C17 1 0.020127 0.168518 0.349772 11.00000 0.03437 0.02866 = 0.02762 -0.00156 0.00109 0.00002 AFIX 43 H7 2 -0.009008 0.166745 0.286892 11.00000 -1.20000 AFIX 0 C18 1 0.035910 0.231422 0.393319 11.00000 0.02764 0.02281 = 0.02961 0.00217 0.00293 0.00009 C19 1 0.268470 0.351697 0.377216 11.00000 0.02874 0.03208 = 0.02975 -0.00018 0.00482 -0.00159 AFIX 13 H20 2 0.284697 0.318916 0.428144 11.00000 -1.20000 AFIX 0 C20 1 0.300977 0.423109 0.415342 11.00000 0.03928 0.04062 = 0.04395 -0.00939 0.00066 -0.00735 AFIX 137 H21 2 0.289494 0.456234 0.366581 11.00000 -1.50000 H22 2 0.403478 0.424932 0.448398 11.00000 -1.50000 H23 2 0.230804 0.433954 0.455493 11.00000 -1.50000 AFIX 0 C21 1 0.375301 0.332228 0.313941 11.00000 0.03310 0.06180 = 0.04858 -0.01469 0.01051 -0.00318 AFIX 137 H24 2 0.351360 0.286331 0.290652 11.00000 -1.50000 H25 2 0.478381 0.333216 0.346219 11.00000 -1.50000 H26 2 0.364603 0.364663 0.264416 11.00000 -1.50000 AFIX 0 C22 1 0.109240 0.344088 0.330637 11.00000 0.03012 0.02452 = 0.02383 -0.00128 0.00499 0.00010 C23 1 0.010191 0.292650 0.335555 11.00000 0.02906 0.02396 = 0.02444 -0.00071 0.00356 0.00121 C24 1 -0.126954 0.348952 0.224554 11.00000 0.03065 0.02328 = 0.02468 0.00026 0.00563 -0.00203 C25 1 -0.253076 0.364269 0.153248 11.00000 0.03009 0.02481 = 0.02646 -0.00033 0.00358 0.00083 C26 1 -0.381808 0.324780 0.145901 11.00000 0.03061 0.02923 = 0.03810 0.00338 0.00419 -0.00044 AFIX 43 H8 2 -0.388767 0.290229 0.188583 11.00000 -1.20000 AFIX 0 C27 1 -0.499639 0.335585 0.076785 11.00000 0.03100 0.03972 = 0.04872 0.00014 -0.00156 -0.00395 AFIX 43 H9 2 -0.586245 0.307752 0.071410 11.00000 -1.20000 AFIX 0 C28 1 -0.491902 0.386730 0.015482 11.00000 0.03841 0.04790 = 0.03857 0.00174 -0.00794 0.00539 AFIX 43 H10 2 -0.572870 0.393970 -0.032047 11.00000 -1.20000 AFIX 0 C29 1 -0.366185 0.427232 0.023551 11.00000 0.04278 0.04293 = 0.03240 0.00928 0.00074 0.00323 AFIX 43 H11 2 -0.361857 0.463131 -0.017664 11.00000 -1.20000 AFIX 0 C30 1 -0.246026 0.415808 0.091551 11.00000 0.03479 0.03384 = 0.03078 0.00347 0.00283 -0.00136 AFIX 43 H12 2 -0.158892 0.443209 0.095966 11.00000 -1.20000 AFIX 0 N1 4 0.223396 0.309329 0.594989 11.00000 0.03249 0.02714 = 0.02535 -0.00051 0.00301 0.00201 N2 4 -0.122032 0.295226 0.275391 11.00000 0.03015 0.02406 = 0.02603 0.00061 0.00242 -0.00028 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM REM R1 = 0.0485 for 5445 Fo > 4sig(Fo) and 0.0562 for all 6090 data REM 329 parameters refined using 0 restraints END WGHT 0.0448 1.1811 REM Highest difference peak 0.264, deepest hole -0.296, 1-sigma level 0.048 Q1 1 -0.1037 0.3425 0.5194 11.00000 0.05 0.26 Q2 1 -0.1233 0.0978 0.3846 11.00000 0.05 0.26 Q3 1 -0.1888 0.3537 0.1739 11.00000 0.05 0.23 Q4 1 0.0343 0.1149 0.4411 11.00000 0.05 0.23 Q5 1 0.0214 0.0904 0.3860 11.00000 0.05 0.22 Q6 1 0.0207 0.3095 0.5559 11.00000 0.05 0.21 Q7 1 0.0818 0.3063 0.3196 11.00000 0.05 0.21 Q8 1 -0.2811 0.2962 0.5118 11.00000 0.05 0.21 Q9 1 0.0507 0.1985 0.3679 11.00000 0.05 0.20 Q10 1 0.1168 0.1474 0.5138 11.00000 0.05 0.20 Q11 1 0.0573 0.2339 0.4380 11.00000 0.05 0.20 Q12 1 0.0828 0.2028 0.5051 11.00000 0.05 0.20 Q13 1 0.0283 0.2518 0.3783 11.00000 0.05 0.20 Q14 1 0.0939 0.3638 0.2818 11.00000 0.05 0.20 Q15 1 0.0484 0.3308 0.5161 11.00000 0.05 0.19 Q16 1 0.1854 0.3479 0.3538 11.00000 0.05 0.19 Q17 1 0.4125 0.3676 0.7155 11.00000 0.05 0.19 Q18 1 -0.2304 0.3466 0.5192 11.00000 0.05 0.19 Q19 1 -0.1025 0.3996 0.2534 11.00000 0.05 0.19 Q20 1 0.0800 0.2670 0.5211 11.00000 0.05 0.18 ; _shelx_res_checksum 55515 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.12048(13) 0.05242(5) 0.53393(8) 0.0415(3) Uani 1 1 d . . . . . F2 F 0.03100(15) 0.04898(5) 0.35525(8) 0.0461(3) Uani 1 1 d . . . . . S1 S 0.05118(5) 0.40950(2) 0.61301(3) 0.03016(12) Uani 1 1 d . . . . . S2 S 0.03098(5) 0.40026(2) 0.24809(3) 0.02803(12) Uani 1 1 d . . . . . C1 C -0.17887(19) 0.34691(9) 0.49186(13) 0.0311(4) Uani 1 1 d . . . . . H13 H -0.1947 0.3068 0.4510 0.037 Uiso 1 1 calc R U . . . C2 C -0.2869(2) 0.34071(12) 0.55853(17) 0.0514(6) Uani 1 1 d . . . . . H14 H -0.2605 0.3007 0.5963 0.077 Uiso 1 1 calc R U . . . H15 H -0.3893 0.3359 0.5261 0.077 Uiso 1 1 calc R U . . . H16 H -0.2798 0.3816 0.5958 0.077 Uiso 1 1 calc R U . . . C3 C -0.2126(2) 0.41102(9) 0.43586(14) 0.0372(4) Uani 1 1 d . . . . . H17 H -0.2041 0.4509 0.4750 0.056 Uiso 1 1 calc R U . . . H18 H -0.3142 0.4084 0.4018 0.056 Uiso 1 1 calc R U . . . H19 H -0.1410 0.4150 0.3948 0.056 Uiso 1 1 calc R U . . . C4 C -0.01918(19) 0.34562(8) 0.53953(12) 0.0270(3) Uani 1 1 d . . . . . C5 C 0.08897(19) 0.29760(8) 0.53882(11) 0.0257(3) Uani 1 1 d . . . . . C6 C 0.22074(19) 0.36666(8) 0.63747(12) 0.0281(4) Uani 1 1 d . . . . . C7 C 0.3511(2) 0.39523(9) 0.69671(12) 0.0302(4) Uani 1 1 d . . . . . C8 C 0.4803(2) 0.35617(11) 0.71686(15) 0.0426(5) Uani 1 1 d . . . . . H1 H 0.4804 0.3106 0.6960 0.051 Uiso 1 1 calc R U . . . C9 C 0.6087(2) 0.38297(13) 0.76703(16) 0.0504(6) Uani 1 1 d . . . . . H2 H 0.6960 0.3557 0.7808 0.060 Uiso 1 1 calc R U . . . C10 C 0.6100(2) 0.44948(12) 0.79713(15) 0.0468(5) Uani 1 1 d . . . . . H3 H 0.6994 0.4686 0.8292 0.056 Uiso 1 1 calc R U . . . C11 C 0.4814(2) 0.48786(11) 0.78053(14) 0.0440(5) Uani 1 1 d . . . . . H4 H 0.4812 0.5329 0.8031 0.053 Uiso 1 1 calc R U . . . C12 C 0.3521(2) 0.46097(9) 0.73090(13) 0.0374(4) Uani 1 1 d . . . . . H5 H 0.2635 0.4876 0.7202 0.045 Uiso 1 1 calc R U . . . C13 C 0.07509(18) 0.23323(8) 0.48634(12) 0.0264(3) Uani 1 1 d . . . . . C14 C 0.10429(19) 0.17227(8) 0.53358(12) 0.0285(4) Uani 1 1 d . . . . . H6 H 0.1334 0.1730 0.5965 0.034 Uiso 1 1 calc R U . . . C15 C 0.09075(19) 0.11121(8) 0.48857(13) 0.0304(4) Uani 1 1 d . . . . . C16 C 0.0466(2) 0.10945(8) 0.39766(13) 0.0325(4) Uani 1 1 d . . . . . C17 C 0.0201(2) 0.16852(9) 0.34977(13) 0.0307(4) Uani 1 1 d . . . . . H7 H -0.0090 0.1667 0.2869 0.037 Uiso 1 1 calc R U . . . C18 C 0.03591(19) 0.23142(8) 0.39332(12) 0.0269(4) Uani 1 1 d . . . . . C19 C 0.26847(19) 0.35170(9) 0.37722(12) 0.0302(4) Uani 1 1 d . . . . . H20 H 0.2847 0.3189 0.4281 0.036 Uiso 1 1 calc R U . . . C20 C 0.3010(2) 0.42311(10) 0.41534(15) 0.0421(5) Uani 1 1 d . . . . . H21 H 0.2895 0.4562 0.3666 0.063 Uiso 1 1 calc R U . . . H22 H 0.4035 0.4249 0.4484 0.063 Uiso 1 1 calc R U . . . H23 H 0.2308 0.4340 0.4555 0.063 Uiso 1 1 calc R U . . . C21 C 0.3753(2) 0.33223(12) 0.31394(16) 0.0474(5) Uani 1 1 d . . . . . H24 H 0.3514 0.2863 0.2907 0.071 Uiso 1 1 calc R U . . . H25 H 0.4784 0.3332 0.3462 0.071 Uiso 1 1 calc R U . . . H26 H 0.3646 0.3647 0.2644 0.071 Uiso 1 1 calc R U . . . C22 C 0.10924(19) 0.34409(8) 0.33064(11) 0.0261(3) Uani 1 1 d . . . . . C23 C 0.01019(18) 0.29265(8) 0.33555(11) 0.0259(3) Uani 1 1 d . . . . . C24 C -0.12695(19) 0.34895(8) 0.22455(12) 0.0261(3) Uani 1 1 d . . . . . C25 C -0.25308(19) 0.36427(8) 0.15325(12) 0.0273(4) Uani 1 1 d . . . . . C26 C -0.3818(2) 0.32478(9) 0.14590(13) 0.0329(4) Uani 1 1 d . . . . . H8 H -0.3888 0.2902 0.1886 0.039 Uiso 1 1 calc R U . . . C27 C -0.4996(2) 0.33558(10) 0.07679(15) 0.0408(5) Uani 1 1 d . . . . . H9 H -0.5862 0.3078 0.0714 0.049 Uiso 1 1 calc R U . . . C28 C -0.4919(2) 0.38673(11) 0.01548(14) 0.0434(5) Uani 1 1 d . . . . . H10 H -0.5729 0.3940 -0.0320 0.052 Uiso 1 1 calc R U . . . C29 C -0.3662(2) 0.42723(10) 0.02355(14) 0.0400(5) Uani 1 1 d . . . . . H11 H -0.3619 0.4631 -0.0177 0.048 Uiso 1 1 calc R U . . . C30 C -0.2460(2) 0.41581(9) 0.09155(13) 0.0335(4) Uani 1 1 d . . . . . H12 H -0.1589 0.4432 0.0960 0.040 Uiso 1 1 calc R U . . . N1 N 0.22340(16) 0.30933(7) 0.59499(10) 0.0286(3) Uani 1 1 d . . . . . N2 N -0.12203(16) 0.29523(7) 0.27539(10) 0.0270(3) 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 0.0549(7) 0.0222(5) 0.0455(7) 0.0097(5) 0.0034(5) 0.0043(4) F2 0.0671(8) 0.0211(5) 0.0461(7) -0.0061(5) -0.0014(6) 0.0005(5) S1 0.0330(2) 0.0276(2) 0.0298(2) -0.00329(17) 0.00531(18) 0.00356(16) S2 0.0314(2) 0.0261(2) 0.0261(2) 0.00295(16) 0.00374(17) -0.00409(15) C1 0.0278(9) 0.0288(8) 0.0368(11) -0.0002(7) 0.0059(7) 0.0010(6) C2 0.0364(11) 0.0618(14) 0.0585(15) 0.0162(12) 0.0157(10) -0.0009(10) C3 0.0334(10) 0.0358(9) 0.0412(11) 0.0052(8) 0.0034(8) 0.0040(7) C4 0.0313(9) 0.0243(8) 0.0257(9) 0.0021(6) 0.0061(7) 0.0005(6) C5 0.0307(8) 0.0235(7) 0.0228(8) 0.0027(6) 0.0042(7) 0.0004(6) C6 0.0325(9) 0.0283(8) 0.0234(9) 0.0007(7) 0.0048(7) 0.0025(6) C7 0.0355(9) 0.0324(9) 0.0227(9) -0.0003(7) 0.0048(7) 0.0006(7) C8 0.0390(11) 0.0446(11) 0.0418(12) -0.0107(9) 0.0005(9) 0.0072(8) C9 0.0362(11) 0.0683(14) 0.0441(13) -0.0139(11) -0.0002(9) 0.0078(10) C10 0.0396(11) 0.0669(14) 0.0327(11) -0.0112(10) 0.0028(9) -0.0108(10) C11 0.0510(12) 0.0431(11) 0.0363(11) -0.0092(9) 0.0033(9) -0.0082(9) C12 0.0431(11) 0.0337(9) 0.0334(10) -0.0035(8) 0.0011(8) 0.0011(8) C13 0.0257(8) 0.0235(8) 0.0297(9) 0.0013(7) 0.0044(7) 0.0013(6) C14 0.0297(8) 0.0274(8) 0.0284(9) 0.0028(7) 0.0047(7) 0.0006(6) C15 0.0310(9) 0.0218(8) 0.0380(10) 0.0083(7) 0.0048(7) 0.0022(6) C16 0.0365(9) 0.0204(8) 0.0396(11) -0.0031(7) 0.0041(8) 0.0008(6) C17 0.0344(9) 0.0287(8) 0.0276(9) -0.0016(7) 0.0011(7) 0.0000(7) C18 0.0276(8) 0.0228(7) 0.0296(9) 0.0022(7) 0.0029(7) 0.0001(6) C19 0.0287(8) 0.0321(9) 0.0297(10) -0.0002(7) 0.0048(7) -0.0016(7) C20 0.0393(11) 0.0406(10) 0.0440(12) -0.0094(9) 0.0007(9) -0.0073(8) C21 0.0331(10) 0.0618(13) 0.0486(14) -0.0147(11) 0.0105(9) -0.0032(9) C22 0.0301(8) 0.0245(7) 0.0238(9) -0.0013(6) 0.0050(7) 0.0001(6) C23 0.0291(8) 0.0240(8) 0.0244(9) -0.0007(6) 0.0036(7) 0.0012(6) C24 0.0307(8) 0.0233(7) 0.0247(9) 0.0003(6) 0.0056(7) -0.0020(6) C25 0.0301(8) 0.0248(8) 0.0265(9) -0.0003(7) 0.0036(7) 0.0008(6) C26 0.0306(9) 0.0292(8) 0.0381(11) 0.0034(7) 0.0042(8) -0.0004(7) C27 0.0310(9) 0.0397(10) 0.0487(13) 0.0001(9) -0.0016(9) -0.0040(8) C28 0.0384(11) 0.0479(11) 0.0386(12) 0.0017(9) -0.0079(9) 0.0054(9) C29 0.0428(11) 0.0429(10) 0.0324(11) 0.0093(8) 0.0007(8) 0.0032(8) C30 0.0348(9) 0.0338(9) 0.0308(10) 0.0035(7) 0.0028(8) -0.0014(7) N1 0.0325(8) 0.0271(7) 0.0254(8) -0.0005(6) 0.0030(6) 0.0020(6) N2 0.0301(7) 0.0241(7) 0.0260(8) 0.0006(6) 0.0024(6) -0.0003(5) 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 C4 S1 C6 90.13(8) . . ? C22 S2 C24 90.06(8) . . ? C4 C1 C3 111.59(14) . . ? C4 C1 C2 110.58(17) . . ? C3 C1 C2 110.33(16) . . ? C5 C4 C1 130.00(16) . . ? C5 C4 S1 108.73(13) . . ? C1 C4 S1 121.18(12) . . ? C4 C5 N1 116.08(15) . . ? C4 C5 C13 126.67(15) . . ? N1 C5 C13 117.21(14) . . ? N1 C6 C7 123.62(16) . . ? N1 C6 S1 113.84(13) . . ? C7 C6 S1 122.45(13) . . ? C8 C7 C12 118.60(17) . . ? C8 C7 C6 118.94(16) . . ? C12 C7 C6 122.42(16) . . ? C9 C8 C7 120.68(19) . . ? C8 C9 C10 120.1(2) . . ? C11 C10 C9 119.84(19) . . ? C10 C11 C12 120.22(19) . . ? C11 C12 C7 120.49(19) . . ? C14 C13 C18 119.44(15) . . ? C14 C13 C5 117.35(15) . . ? C18 C13 C5 123.21(14) . . ? C15 C14 C13 119.79(17) . . ? F1 C15 C16 119.50(15) . . ? F1 C15 C14 119.86(16) . . ? C16 C15 C14 120.63(15) . . ? F2 C16 C17 119.80(17) . . ? F2 C16 C15 119.58(15) . . ? C17 C16 C15 120.62(16) . . ? C16 C17 C18 120.12(17) . . ? C17 C18 C13 119.33(15) . . ? C17 C18 C23 116.22(16) . . ? C13 C18 C23 124.45(15) . . ? C22 C19 C20 112.19(15) . . ? C22 C19 C21 109.88(16) . . ? C20 C19 C21 111.56(16) . . ? C23 C22 C19 129.58(15) . . ? C23 C22 S2 108.68(12) . . ? C19 C22 S2 121.36(12) . . ? C22 C23 N2 116.28(15) . . ? C22 C23 C18 126.52(15) . . ? N2 C23 C18 116.96(14) . . ? N2 C24 C25 123.21(15) . . ? N2 C24 S2 113.80(12) . . ? C25 C24 S2 122.99(12) . . ? C30 C25 C26 119.17(16) . . ? C30 C25 C24 121.93(15) . . ? C26 C25 C24 118.87(15) . . ? C27 C26 C25 120.33(18) . . ? C28 C27 C26 120.26(18) . . ? C29 C28 C27 119.78(18) . . ? C28 C29 C30 120.36(18) . . ? C29 C30 C25 120.06(17) . . ? C6 N1 C5 111.21(14) . . ? C24 N2 C23 111.15(14) . . ? 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 C15 1.3497(18) . ? F2 C16 1.3486(19) . ? S1 C4 1.7299(17) . ? S1 C6 1.7384(17) . ? S2 C22 1.7318(17) . ? S2 C24 1.7395(17) . ? C1 C4 1.507(2) . ? C1 C3 1.523(2) . ? C1 C2 1.534(3) . ? C4 C5 1.364(2) . ? C5 N1 1.385(2) . ? C5 C13 1.491(2) . ? C6 N1 1.302(2) . ? C6 C7 1.471(2) . ? C7 C8 1.391(3) . ? C7 C12 1.393(2) . ? C8 C9 1.384(3) . ? C9 C10 1.385(3) . ? C10 C11 1.377(3) . ? C11 C12 1.387(3) . ? C13 C14 1.400(2) . ? C13 C18 1.402(2) . ? C14 C15 1.377(2) . ? C15 C16 1.375(3) . ? C16 C17 1.370(2) . ? C17 C18 1.399(2) . ? C18 C23 1.486(2) . ? C19 C22 1.505(2) . ? C19 C20 1.528(2) . ? C19 C21 1.530(3) . ? C22 C23 1.364(2) . ? C23 N2 1.381(2) . ? C24 N2 1.306(2) . ? C24 C25 1.468(2) . ? C25 C30 1.391(2) . ? C25 C26 1.392(2) . ? C26 C27 1.383(3) . ? C27 C28 1.382(3) . ? C28 C29 1.380(3) . ? C29 C30 1.388(3) . ? 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 C3 C1 C4 C5 -124.8(2) . . . . ? C2 C1 C4 C5 111.9(2) . . . . ? C3 C1 C4 S1 58.8(2) . . . . ? C2 C1 C4 S1 -64.40(19) . . . . ? C6 S1 C4 C5 -0.15(14) . . . . ? C6 S1 C4 C1 176.89(15) . . . . ? C1 C4 C5 N1 -175.81(17) . . . . ? S1 C4 C5 N1 0.9(2) . . . . ? C1 C4 C5 C13 2.0(3) . . . . ? S1 C4 C5 C13 178.66(14) . . . . ? C4 S1 C6 N1 -0.64(15) . . . . ? C4 S1 C6 C7 175.85(16) . . . . ? N1 C6 C7 C8 -7.4(3) . . . . ? S1 C6 C7 C8 176.50(16) . . . . ? N1 C6 C7 C12 170.26(19) . . . . ? S1 C6 C7 C12 -5.9(3) . . . . ? C12 C7 C8 C9 -2.4(3) . . . . ? C6 C7 C8 C9 175.3(2) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 C11 3.0(4) . . . . ? C9 C10 C11 C12 -2.4(3) . . . . ? C10 C11 C12 C7 -0.6(3) . . . . ? C8 C7 C12 C11 3.0(3) . . . . ? C6 C7 C12 C11 -174.67(19) . . . . ? C4 C5 C13 C14 -122.90(19) . . . . ? N1 C5 C13 C14 54.9(2) . . . . ? C4 C5 C13 C18 57.6(3) . . . . ? N1 C5 C13 C18 -124.61(18) . . . . ? C18 C13 C14 C15 -1.6(3) . . . . ? C5 C13 C14 C15 178.94(16) . . . . ? C13 C14 C15 F1 179.26(15) . . . . ? C13 C14 C15 C16 -1.0(3) . . . . ? F1 C15 C16 F2 1.2(3) . . . . ? C14 C15 C16 F2 -178.56(16) . . . . ? F1 C15 C16 C17 -178.03(16) . . . . ? C14 C15 C16 C17 2.2(3) . . . . ? F2 C16 C17 C18 179.91(16) . . . . ? C15 C16 C17 C18 -0.9(3) . . . . ? C16 C17 C18 C13 -1.7(3) . . . . ? C16 C17 C18 C23 177.85(16) . . . . ? C14 C13 C18 C17 2.9(3) . . . . ? C5 C13 C18 C17 -177.67(16) . . . . ? C14 C13 C18 C23 -176.63(16) . . . . ? C5 C13 C18 C23 2.8(3) . . . . ? C20 C19 C22 C23 -135.1(2) . . . . ? C21 C19 C22 C23 100.2(2) . . . . ? C20 C19 C22 S2 52.9(2) . . . . ? C21 C19 C22 S2 -71.86(19) . . . . ? C24 S2 C22 C23 -1.49(14) . . . . ? C24 S2 C22 C19 172.06(15) . . . . ? C19 C22 C23 N2 -171.20(17) . . . . ? S2 C22 C23 N2 1.7(2) . . . . ? C19 C22 C23 C18 3.0(3) . . . . ? S2 C22 C23 C18 175.83(14) . . . . ? C17 C18 C23 C22 -121.9(2) . . . . ? C13 C18 C23 C22 57.6(3) . . . . ? C17 C18 C23 N2 52.3(2) . . . . ? C13 C18 C23 N2 -128.23(18) . . . . ? C22 S2 C24 N2 1.12(14) . . . . ? C22 S2 C24 C25 -178.07(15) . . . . ? N2 C24 C25 C30 -170.01(17) . . . . ? S2 C24 C25 C30 9.1(2) . . . . ? N2 C24 C25 C26 8.2(3) . . . . ? S2 C24 C25 C26 -172.65(14) . . . . ? C30 C25 C26 C27 1.6(3) . . . . ? C24 C25 C26 C27 -176.67(18) . . . . ? C25 C26 C27 C28 -1.4(3) . . . . ? C26 C27 C28 C29 -0.2(3) . . . . ? C27 C28 C29 C30 1.6(3) . . . . ? C28 C29 C30 C25 -1.4(3) . . . . ? C26 C25 C30 C29 -0.2(3) . . . . ? C24 C25 C30 C29 178.03(18) . . . . ? C7 C6 N1 C5 -175.22(16) . . . . ? S1 C6 N1 C5 1.22(19) . . . . ? C4 C5 N1 C6 -1.4(2) . . . . ? C13 C5 N1 C6 -179.39(15) . . . . ? C25 C24 N2 C23 178.81(16) . . . . ? S2 C24 N2 C23 -0.39(19) . . . . ? C22 C23 N2 C24 -0.9(2) . . . . ? C18 C23 N2 C24 -175.61(15) . . . . ?