#------------------------------------------------------------------------------ #$Date: 2019-11-17 15:29:49 +0200 (Sun, 17 Nov 2019) $ #$Revision: 230890 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/90/1549092.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_1549092 loop_ _publ_author_name 'Al Mousawi, Assi' 'Arar, Ahmad' 'Ibrahim-Ouali, Malika' 'Duval, Sylvain' 'Dumur, Fr\'ed\'eric' 'Garra, Patxi' 'Toufaily, Joumana' 'Hamieh, Tayssir' 'Graff, Bernadette' 'Gigmes, Didier' 'Fouassier, Jean-Pierre' 'Lalev\'ee, Jacques' _publ_section_title ; Carbazole-based compounds as photoinitiators for free radical and cationic polymerization upon near visible light illumination. ; _journal_issue 5 _journal_name_full 'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology' _journal_page_first 578 _journal_page_last 585 _journal_paper_doi 10.1039/c7pp00400a _journal_volume 17 _journal_year 2018 _chemical_formula_moiety 'C28 H34 N2 O4 S' _chemical_formula_sum 'C28 H34 N2 O4 S' _chemical_formula_weight 494.55 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2017-01-16 _audit_creation_method ; Olex2 1.2 (compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292) ; _audit_update_record ; 2017-10-26 deposited with the CCDC. 2018-03-20 downloaded from the CCDC. ; _cell_angle_alpha 102.821(4) _cell_angle_beta 90.215(4) _cell_angle_gamma 102.549(4) _cell_formula_units_Z 2 _cell_length_a 10.0007(10) _cell_length_b 10.5374(11) _cell_length_c 12.7404(13) _cell_measurement_reflns_used 8985 _cell_measurement_temperature 100 _cell_measurement_theta_max 26.27 _cell_measurement_theta_min 2.59 _cell_volume 1275.9(2) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'olex2.solve (Bourhis et al., 2015)' _diffrn_ambient_temperature 100.06 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_unetI/netI 0.0372 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 23651 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.400 _diffrn_reflns_theta_min 1.642 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6746 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'SADABS 'numerical'' _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.287 _exptl_crystal_description block _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _refine_diff_density_max 1.146 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 322 _refine_ls_number_reflns 5138 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0519 _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^)+(0.0494P)^2^+1.8409P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1223 _refine_ls_wR_factor_ref 0.1328 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4102 _reflns_number_total 5138 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7pp00400a2.cif _cod_data_source_block fd01 _cod_depositor_comments 'Adding full bibliography for 1549092.cif.' _cod_database_code 1549092 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C24(H24) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C23(H23A,H23B), C25(H25A,H25B), C27(H27A,H27B) 2.c Aromatic/amide H refined with riding coordinates: N2(H2), C2(H2A), C6(H6), C21(H21), C19(H19), C5(H5), C3(H3), C22(H22), C20(H20), C10(H10) 2.d Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C7(H7A,H7B,H7C), C26(H26A,H26B, H26C), C28(H28A,H28B,H28C) ; _shelx_res_file ; fd01.res created by SHELXL-2014/7 TITL CELL 0.71073 10.0007 10.5374 12.7404 102.8212 90.215 102.5492 ZERR 2 0.001 0.0011 0.0013 0.0039 0.0043 0.004 LATT 1 SFAC C H N O S UNIT 56 68 4 7.99 2 L.S. 10 PLAN 6 TEMP -173.09 fmap 2 acta REM REM REM WGHT 0.049400 1.840900 FVAR 0.17864 S1 5 0.107049 0.864407 0.281657 11.00000 0.02202 0.01385 = 0.01308 0.00421 0.00091 0.00270 O1 4 0.225212 0.862880 0.218699 11.00000 0.02221 0.02241 = 0.01803 0.00612 0.00312 -0.00042 O2 4 0.069762 0.988566 0.328481 11.00000 0.03702 0.01386 = 0.01968 0.00280 0.00115 0.00729 C1 1 0.124942 0.783867 0.387494 11.00000 0.01795 0.01448 = 0.01362 0.00310 -0.00140 0.00118 N2 3 -0.440846 0.430170 -0.177033 11.00000 0.01389 0.01659 = 0.01836 0.00293 -0.00102 0.00077 AFIX 43 H2 2 -0.510638 0.360900 -0.185701 11.00000 -1.20000 AFIX 0 C2 1 0.061135 0.817363 0.483304 11.00000 0.02335 0.01683 = 0.01700 0.00188 0.00082 0.00677 AFIX 43 H2A 2 0.012954 0.887212 0.494157 11.00000 -1.20000 AFIX 0 C6 1 0.195750 0.681606 0.371128 11.00000 0.01709 0.02054 = 0.01394 0.00252 0.00013 0.00365 AFIX 43 H6 2 0.239456 0.659214 0.305667 11.00000 -1.20000 AFIX 0 C21 1 -0.328311 0.725738 -0.345531 11.00000 0.02938 0.02084 = 0.01926 0.00709 0.00128 0.00945 AFIX 43 H21 2 -0.299815 0.795865 -0.381843 11.00000 -1.20000 AFIX 0 C19 1 -0.493912 0.525444 -0.331385 11.00000 0.01885 0.02400 = 0.01958 0.00024 -0.00441 0.00553 AFIX 43 H19 2 -0.575561 0.459801 -0.356628 11.00000 -1.20000 AFIX 0 C13 1 -0.242247 0.580340 -0.109615 11.00000 0.01637 0.01486 = 0.01267 0.00188 0.00337 0.00437 C17 1 -0.291927 0.616006 -0.204482 11.00000 0.01624 0.01709 = 0.01236 0.00072 0.00159 0.00627 C12 1 -0.338796 0.466887 -0.095461 11.00000 0.01364 0.01678 = 0.01479 0.00109 0.00262 0.00559 C5 1 0.201793 0.612677 0.451556 11.00000 0.01949 0.01950 = 0.02084 0.00396 -0.00200 0.00652 AFIX 43 H5 2 0.249737 0.542645 0.440598 11.00000 -1.20000 AFIX 0 C18 1 -0.415343 0.519891 -0.242596 11.00000 0.01640 0.01704 = 0.01657 0.00218 0.00270 0.00627 C11 1 -0.330045 0.407701 -0.008437 11.00000 0.01762 0.01649 = 0.01828 0.00421 0.00566 0.00406 C3 1 0.068580 0.747628 0.562977 11.00000 0.02172 0.02440 = 0.01387 0.00337 0.00234 0.00491 AFIX 43 H3 2 0.025293 0.770474 0.628573 11.00000 -1.20000 AFIX 0 C22 1 -0.249528 0.720154 -0.257618 11.00000 0.02018 0.01974 = 0.01552 0.00248 0.00165 0.00378 AFIX 43 H22 2 -0.167721 0.786081 -0.233569 11.00000 -1.20000 AFIX 0 C4 1 0.138422 0.644882 0.548198 11.00000 0.01694 0.02257 = 0.01658 0.00675 -0.00270 0.00188 C15 1 -0.019393 0.753427 -0.053794 11.00000 0.01681 0.01829 = 0.01745 0.00415 -0.00042 0.00020 AFIX 137 H15A 2 -0.000362 0.739643 -0.130401 11.00000 -1.50000 H15B 2 0.064742 0.760173 -0.011242 11.00000 -1.50000 H15C 2 -0.052058 0.836029 -0.031144 11.00000 -1.50000 AFIX 0 C14 1 -0.127783 0.637250 -0.036260 11.00000 0.01465 0.01509 = 0.01437 0.00237 0.00348 0.00371 C20 1 -0.449227 0.629496 -0.381510 11.00000 0.02619 0.02823 = 0.01858 0.00369 -0.00467 0.01116 AFIX 43 H20 2 -0.501727 0.635811 -0.441677 11.00000 -1.20000 AFIX 0 C16 1 -0.437354 0.289002 0.004907 11.00000 0.02194 0.01893 = 0.02457 0.00743 0.00204 0.00065 AFIX 137 H16A 2 -0.527817 0.310825 0.006281 11.00000 -1.50000 H16B 2 -0.417472 0.265586 0.072673 11.00000 -1.50000 H16C 2 -0.436766 0.213172 -0.055529 11.00000 -1.50000 AFIX 0 C7 1 0.146870 0.571165 0.636386 11.00000 0.02920 0.03145 = 0.02298 0.01408 -0.00069 0.00660 AFIX 137 H7A 2 0.140240 0.476350 0.604103 11.00000 -1.50000 H7B 2 0.071280 0.580714 0.684094 11.00000 -1.50000 H7C 2 0.234565 0.608672 0.678097 11.00000 -1.50000 AFIX 0 N1 3 -0.025819 0.771655 0.204736 11.00000 0.01819 0.01867 = 0.01303 0.00267 0.00192 0.00726 C8 1 -0.006656 0.640194 0.140064 11.00000 0.01977 0.01611 = 0.01466 0.00290 0.00008 0.00579 AFIX 23 H8A 2 -0.007425 0.577986 0.188097 11.00000 -1.20000 H8B 2 0.083445 0.653001 0.107236 11.00000 -1.20000 AFIX 0 C9 1 -0.119191 0.580637 0.052458 11.00000 0.01462 0.01804 = 0.01380 0.00278 0.00127 0.00498 C10 1 -0.219574 0.468719 0.064411 11.00000 0.01948 0.01893 = 0.01512 0.00527 0.00267 0.00659 AFIX 43 H10 2 -0.210878 0.433286 0.125828 11.00000 -1.20000 AFIX 0 C23 1 -0.160646 0.766395 0.252140 11.00000 0.02117 0.02500 = 0.01875 0.00346 0.00369 0.00774 AFIX 23 H23A 2 -0.147980 0.775748 0.330810 11.00000 -1.20000 H23B 2 -0.220351 0.677301 0.221985 11.00000 -1.20000 AFIX 0 C24 1 -0.233826 0.871853 0.233415 11.00000 0.01802 0.02393 = 0.03666 0.00666 0.00096 0.00441 AFIX 13 H24 2 -0.187944 0.961532 0.278265 11.00000 -1.20000 AFIX 0 PART 1 O4 4 -0.370066 0.833448 0.263840 0.99542 0.01742 0.02225 = 0.04510 -0.00091 0.00610 0.00218 PART 0 O3 4 -0.236850 0.874566 0.126096 11.00000 0.04138 0.02859 = 0.03246 0.00479 -0.00663 0.01466 C26 1 -0.276750 0.977201 -0.014956 11.00000 0.02665 0.02341 = 0.03923 0.00887 -0.00053 0.00404 AFIX 137 H26A 2 -0.331004 0.889416 -0.052204 11.00000 -1.50000 H26B 2 -0.181890 0.986964 -0.036816 11.00000 -1.50000 H26C 2 -0.315919 1.047224 -0.033933 11.00000 -1.50000 AFIX 0 C25 1 -0.278921 0.989289 0.103031 11.00000 0.03866 0.02917 = 0.03512 0.01377 0.00757 0.00648 AFIX 23 H25A 2 -0.215307 1.072795 0.141216 11.00000 -1.20000 H25B 2 -0.372444 0.991431 0.127422 11.00000 -1.20000 AFIX 0 C27 1 -0.403297 0.909890 0.362953 11.00000 0.04411 0.03671 = 0.04312 -0.00311 0.01480 0.00649 AFIX 23 H27A 2 -0.324300 0.928861 0.415487 11.00000 -1.20000 H27B 2 -0.481888 0.854565 0.390949 11.00000 -1.20000 AFIX 0 C28 1 -0.438267 1.037451 0.358508 11.00000 0.05411 0.04300 = 0.05199 0.00496 0.01888 0.01882 AFIX 137 H28A 2 -0.514953 1.020918 0.305502 11.00000 -1.50000 H28B 2 -0.358503 1.096934 0.337425 11.00000 -1.50000 H28C 2 -0.464607 1.079359 0.429639 11.00000 -1.50000 AFIX 0 HKLF 4 REM REM R1 = 0.0519 for 4102 Fo > 4sig(Fo) and 0.0687 for all 5138 data REM 322 parameters refined using 0 restraints END WGHT 0.0494 1.8409 REM Highest difference peak 1.146, deepest hole -0.510, 1-sigma level 0.066 Q1 1 -0.1849 0.9737 0.1835 11.00000 0.05 1.15 Q2 1 -0.3562 0.8126 0.3269 11.00000 0.05 0.71 Q3 1 -0.4731 0.9181 0.3118 11.00000 0.05 0.70 Q4 1 -0.1951 0.9776 0.1281 11.00000 0.05 0.69 Q5 1 -0.3834 0.8754 0.4457 11.00000 0.05 0.53 Q6 1 -0.2770 0.8362 0.1764 11.00000 0.05 0.46 ; _shelx_res_checksum 88984 _olex2_exptl_crystal_mounting_method 'mitegen loop' _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.10705(6) 0.86441(5) 0.28166(4) 0.01634(15) Uani 1 1 d . . . O1 O 0.22521(17) 0.86288(16) 0.21870(13) 0.0215(4) Uani 1 1 d . . . O2 O 0.06976(18) 0.98857(16) 0.32848(13) 0.0234(4) Uani 1 1 d . . . C1 C 0.1249(2) 0.7839(2) 0.38749(17) 0.0158(5) Uani 1 1 d . . . N2 N -0.44085(19) 0.43017(19) -0.17703(15) 0.0169(4) Uani 1 1 d . . . H2 H -0.5106 0.3609 -0.1857 0.020 Uiso 1 1 calc R . . C2 C 0.0611(2) 0.8174(2) 0.48330(18) 0.0190(5) Uani 1 1 d . . . H2A H 0.0130 0.8872 0.4942 0.023 Uiso 1 1 calc R . . C6 C 0.1957(2) 0.6816(2) 0.37113(18) 0.0175(5) Uani 1 1 d . . . H6 H 0.2395 0.6592 0.3057 0.021 Uiso 1 1 calc R . . C21 C -0.3283(3) 0.7257(2) -0.34553(19) 0.0222(5) Uani 1 1 d . . . H21 H -0.2998 0.7959 -0.3818 0.027 Uiso 1 1 calc R . . C19 C -0.4939(2) 0.5254(2) -0.33138(19) 0.0215(5) Uani 1 1 d . . . H19 H -0.5756 0.4598 -0.3566 0.026 Uiso 1 1 calc R . . C13 C -0.2422(2) 0.5803(2) -0.10962(17) 0.0147(4) Uani 1 1 d . . . C17 C -0.2919(2) 0.6160(2) -0.20448(17) 0.0153(5) Uani 1 1 d . . . C12 C -0.3388(2) 0.4669(2) -0.09546(17) 0.0151(5) Uani 1 1 d . . . C5 C 0.2018(2) 0.6127(2) 0.45156(19) 0.0197(5) Uani 1 1 d . . . H5 H 0.2497 0.5426 0.4406 0.024 Uiso 1 1 calc R . . C18 C -0.4153(2) 0.5199(2) -0.24260(18) 0.0165(5) Uani 1 1 d . . . C11 C -0.3300(2) 0.4077(2) -0.00844(18) 0.0174(5) Uani 1 1 d . . . C3 C 0.0686(2) 0.7476(2) 0.56298(18) 0.0202(5) Uani 1 1 d . . . H3 H 0.0253 0.7705 0.6286 0.024 Uiso 1 1 calc R . . C22 C -0.2495(2) 0.7202(2) -0.25762(18) 0.0188(5) Uani 1 1 d . . . H22 H -0.1677 0.7861 -0.2336 0.023 Uiso 1 1 calc R . . C4 C 0.1384(2) 0.6449(2) 0.54820(18) 0.0187(5) Uani 1 1 d . . . C15 C -0.0194(2) 0.7534(2) -0.05379(18) 0.0181(5) Uani 1 1 d . . . H15A H -0.0004 0.7396 -0.1304 0.027 Uiso 1 1 calc GR . . H15B H 0.0647 0.7602 -0.0112 0.027 Uiso 1 1 calc GR . . H15C H -0.0521 0.8360 -0.0311 0.027 Uiso 1 1 calc GR . . C14 C -0.1278(2) 0.6373(2) -0.03626(17) 0.0148(4) Uani 1 1 d . . . C20 C -0.4492(3) 0.6295(3) -0.38151(19) 0.0238(5) Uani 1 1 d . . . H20 H -0.5017 0.6358 -0.4417 0.029 Uiso 1 1 calc R . . C16 C -0.4374(2) 0.2890(2) 0.0049(2) 0.0220(5) Uani 1 1 d . . . H16A H -0.5278 0.3108 0.0063 0.033 Uiso 1 1 calc GR . . H16B H -0.4175 0.2656 0.0727 0.033 Uiso 1 1 calc GR . . H16C H -0.4368 0.2132 -0.0555 0.033 Uiso 1 1 calc GR . . C7 C 0.1469(3) 0.5712(3) 0.6364(2) 0.0267(6) Uani 1 1 d . . . H7A H 0.1402 0.4764 0.6041 0.040 Uiso 1 1 calc GR . . H7B H 0.0713 0.5807 0.6841 0.040 Uiso 1 1 calc GR . . H7C H 0.2346 0.6087 0.6781 0.040 Uiso 1 1 calc GR . . N1 N -0.02582(19) 0.77165(19) 0.20474(14) 0.0163(4) Uani 1 1 d . . . C8 C -0.0067(2) 0.6402(2) 0.14006(17) 0.0167(5) Uani 1 1 d . . . H8A H -0.0074 0.5780 0.1881 0.020 Uiso 1 1 calc R . . H8B H 0.0834 0.6530 0.1072 0.020 Uiso 1 1 calc R . . C9 C -0.1192(2) 0.5806(2) 0.05246(17) 0.0154(5) Uani 1 1 d . . . C10 C -0.2196(2) 0.4687(2) 0.06441(18) 0.0173(5) Uani 1 1 d . . . H10 H -0.2109 0.4333 0.1258 0.021 Uiso 1 1 calc R . . C23 C -0.1606(2) 0.7664(2) 0.25214(19) 0.0215(5) Uani 1 1 d . . . H23A H -0.1480 0.7757 0.3308 0.026 Uiso 1 1 calc R . . H23B H -0.2204 0.6773 0.2220 0.026 Uiso 1 1 calc R . . C24 C -0.2338(2) 0.8719(3) 0.2334(2) 0.0263(6) Uani 1 1 d . . . H24 H -0.1879 0.9615 0.2783 0.032 Uiso 1 1 calc R A . O4 O -0.37007(17) 0.83345(18) 0.26384(16) 0.0300(7) Uani 0.995(7) 1 d . B 1 O3 O -0.2368(2) 0.87457(19) 0.12610(15) 0.0334(5) Uani 1 1 d . . . C26 C -0.2767(3) 0.9772(3) -0.0150(2) 0.0297(6) Uani 1 1 d . . . H26A H -0.3310 0.8894 -0.0522 0.045 Uiso 1 1 calc GR . . H26B H -0.1819 0.9870 -0.0368 0.045 Uiso 1 1 calc GR . . H26C H -0.3159 1.0472 -0.0339 0.045 Uiso 1 1 calc GR . . C25 C -0.2789(3) 0.9893(3) 0.1030(2) 0.0334(6) Uani 1 1 d . . . H25A H -0.2153 1.0728 0.1412 0.040 Uiso 1 1 calc R . . H25B H -0.3724 0.9914 0.1274 0.040 Uiso 1 1 calc R . . C27 C -0.4033(3) 0.9099(3) 0.3630(3) 0.0436(8) Uani 1 1 d . . . H27A H -0.3243 0.9289 0.4155 0.052 Uiso 1 1 calc R B . H27B H -0.4819 0.8546 0.3909 0.052 Uiso 1 1 calc R B . C28 C -0.4383(4) 1.0375(3) 0.3585(3) 0.0494(8) Uani 1 1 d . . . H28A H -0.5150 1.0209 0.3055 0.074 Uiso 1 1 calc GR . . H28B H -0.3585 1.0969 0.3374 0.074 Uiso 1 1 calc GR . . H28C H -0.4646 1.0794 0.4296 0.074 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 0.0220(3) 0.0138(3) 0.0131(3) 0.0042(2) 0.0009(2) 0.0027(2) O1 0.0222(9) 0.0224(9) 0.0180(8) 0.0061(7) 0.0031(7) -0.0004(7) O2 0.0370(10) 0.0139(8) 0.0197(9) 0.0028(7) 0.0011(7) 0.0073(7) C1 0.0179(11) 0.0145(11) 0.0136(11) 0.0031(8) -0.0014(9) 0.0012(9) N2 0.0139(9) 0.0166(10) 0.0184(10) 0.0029(8) -0.0010(7) 0.0008(7) C2 0.0234(12) 0.0168(11) 0.0170(11) 0.0019(9) 0.0008(9) 0.0068(9) C6 0.0171(11) 0.0205(12) 0.0139(11) 0.0025(9) 0.0001(9) 0.0037(9) C21 0.0294(13) 0.0208(12) 0.0193(12) 0.0071(9) 0.0013(10) 0.0094(10) C19 0.0189(12) 0.0240(12) 0.0196(12) 0.0002(10) -0.0044(9) 0.0055(10) C13 0.0164(11) 0.0149(11) 0.0127(10) 0.0019(8) 0.0034(8) 0.0044(9) C17 0.0162(11) 0.0171(11) 0.0124(10) 0.0007(8) 0.0016(8) 0.0063(9) C12 0.0136(11) 0.0168(11) 0.0148(11) 0.0011(9) 0.0026(8) 0.0056(9) C5 0.0195(12) 0.0195(12) 0.0208(12) 0.0040(9) -0.0020(9) 0.0065(9) C18 0.0164(11) 0.0170(11) 0.0166(11) 0.0022(9) 0.0027(9) 0.0063(9) C11 0.0176(11) 0.0165(11) 0.0183(11) 0.0042(9) 0.0057(9) 0.0041(9) C3 0.0217(12) 0.0244(12) 0.0139(11) 0.0034(9) 0.0023(9) 0.0049(10) C22 0.0202(12) 0.0197(12) 0.0155(11) 0.0025(9) 0.0017(9) 0.0038(9) C4 0.0169(11) 0.0226(12) 0.0166(11) 0.0068(9) -0.0027(9) 0.0019(9) C15 0.0168(11) 0.0183(11) 0.0175(11) 0.0041(9) -0.0004(9) 0.0002(9) C14 0.0146(11) 0.0151(11) 0.0144(11) 0.0024(8) 0.0035(8) 0.0037(8) C20 0.0262(13) 0.0282(13) 0.0186(12) 0.0037(10) -0.0047(10) 0.0112(10) C16 0.0219(12) 0.0189(12) 0.0246(13) 0.0074(10) 0.0020(10) 0.0006(10) C7 0.0292(14) 0.0314(14) 0.0230(13) 0.0141(11) -0.0007(10) 0.0066(11) N1 0.0182(10) 0.0187(10) 0.0130(9) 0.0027(8) 0.0019(7) 0.0073(8) C8 0.0198(12) 0.0161(11) 0.0147(11) 0.0029(9) 0.0001(9) 0.0058(9) C9 0.0146(11) 0.0180(11) 0.0138(11) 0.0028(9) 0.0013(8) 0.0050(9) C10 0.0195(12) 0.0189(11) 0.0151(11) 0.0053(9) 0.0027(9) 0.0066(9) C23 0.0212(12) 0.0250(13) 0.0188(12) 0.0035(10) 0.0037(9) 0.0077(10) C24 0.0180(12) 0.0239(13) 0.0367(15) 0.0067(11) 0.0010(11) 0.0044(10) O4 0.0174(10) 0.0222(10) 0.0451(13) -0.0009(8) 0.0061(8) 0.0022(7) O3 0.0414(11) 0.0286(10) 0.0325(11) 0.0048(8) -0.0066(9) 0.0147(9) C26 0.0266(14) 0.0234(13) 0.0392(16) 0.0089(11) -0.0005(12) 0.0040(11) C25 0.0387(16) 0.0292(15) 0.0351(15) 0.0138(12) 0.0076(12) 0.0065(12) C27 0.0441(18) 0.0367(17) 0.0431(18) -0.0031(14) 0.0148(14) 0.0065(14) C28 0.054(2) 0.0430(19) 0.052(2) 0.0050(16) 0.0189(17) 0.0188(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' 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 O1 S1 O2 120.49(10) O1 S1 C1 108.13(10) O1 S1 N1 107.35(10) O2 S1 C1 107.55(10) O2 S1 N1 106.09(10) N1 S1 C1 106.44(10) C2 C1 S1 119.86(17) C2 C1 C6 120.6(2) C6 C1 S1 119.41(17) C18 N2 C12 108.87(18) C3 C2 C1 119.3(2) C5 C6 C1 119.3(2) C22 C21 C20 120.9(2) C20 C19 C18 117.9(2) C12 C13 C17 106.30(19) C14 C13 C17 133.4(2) C14 C13 C12 120.3(2) C18 C17 C13 106.06(19) C22 C17 C13 135.3(2) C22 C17 C18 118.6(2) N2 C12 C13 109.49(19) N2 C12 C11 127.4(2) C11 C12 C13 123.1(2) C6 C5 C4 120.9(2) N2 C18 C19 128.8(2) N2 C18 C17 109.25(19) C19 C18 C17 121.9(2) C12 C11 C16 121.2(2) C10 C11 C12 115.3(2) C10 C11 C16 123.4(2) C2 C3 C4 121.0(2) C21 C22 C17 119.3(2) C5 C4 C7 120.9(2) C3 C4 C5 118.8(2) C3 C4 C7 120.3(2) C13 C14 C15 120.98(19) C9 C14 C13 117.2(2) C9 C14 C15 121.8(2) C19 C20 C21 121.4(2) C8 N1 S1 115.70(15) C23 N1 S1 116.26(15) C23 N1 C8 114.38(18) N1 C8 C9 110.72(18) C14 C9 C8 121.5(2) C14 C9 C10 120.5(2) C10 C9 C8 118.03(19) C11 C10 C9 123.6(2) N1 C23 C24 115.1(2) O4 C24 C23 106.3(2) O3 C24 C23 110.4(2) O3 C24 O4 108.8(2) C24 O4 C27 115.8(2) C24 O3 C25 114.5(2) O3 C25 C26 107.7(2) O4 C27 C28 116.1(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.4317(17) S1 O2 1.4401(17) S1 C1 1.773(2) S1 N1 1.6377(19) C1 C2 1.391(3) C1 C6 1.392(3) N2 C12 1.383(3) N2 C18 1.380(3) C2 C3 1.389(3) C6 C5 1.389(3) C21 C22 1.386(3) C21 C20 1.399(4) C19 C18 1.394(3) C19 C20 1.382(4) C13 C17 1.458(3) C13 C12 1.410(3) C13 C14 1.410(3) C17 C18 1.421(3) C17 C22 1.404(3) C12 C11 1.398(3) C5 C4 1.395(3) C11 C16 1.502(3) C11 C10 1.384(3) C3 C4 1.391(3) C4 C7 1.513(3) C15 C14 1.507(3) C14 C9 1.401(3) N1 C8 1.498(3) N1 C23 1.475(3) C8 C9 1.510(3) C9 C10 1.410(3) C23 C24 1.516(3) C24 O4 1.416(3) C24 O3 1.374(3) O4 C27 1.422(3) O3 C25 1.450(3) C26 C25 1.481(4) C27 C28 1.473(5)