#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:46:42 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258125 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240597.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_7240597 loop_ _publ_author_name 'Arshad, Nasima' 'Rafiq, Mamoona' 'Ujan, Rabail' 'Saeed, Aamer' 'Farooqi, Shahid I.' 'Perveen, Fouzia' 'Channar, Pervaiz Ali' 'Ashraf, Saba' 'Abbas, Qamar' 'Ahmed, Ashfaq' 'Hokelek, Tuncer' 'Kaur, Manpreet' 'Jasinski, Jerry P.' _publ_section_title ; Synthesis, X-ray crystal structure elucidation and Hirshfeld surface analysis of N-((4-(1H-benzo[d]imidazole-2-yl)phenyl)carbamothioyl)benzamide: investigations for elastase inhibition, antioxidant and DNA binding potentials for biological applications ; _journal_issue 35 _journal_name_full 'RSC Advances' _journal_page_first 20837 _journal_page_last 20851 _journal_paper_doi 10.1039/D0RA02501A _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C21 H16 N4 O S, H2 O' _chemical_formula_sum 'C21 H18 N4 O2 S' _chemical_formula_weight 390.45 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-08-02 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-02-25 deposited with the CCDC. 2020-05-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.235(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.9104(3) _cell_length_b 19.6432(7) _cell_length_c 14.0505(5) _cell_measurement_reflns_used 2815 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 31.5460 _cell_measurement_theta_min 3.1490 _cell_volume 1876.90(13) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0416 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.894 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -1.00 89.00 1.00 9.23 -- 25.99 77.00 120.00 90 2 \w -28.00 41.00 1.00 9.23 -- 25.99 -57.00 -90.00 69 3 \w -41.00 53.00 1.00 9.23 -- 25.99 -77.00 0.00 94 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1035015000 _diffrn_orient_matrix_UB_12 -0.0000697000 _diffrn_orient_matrix_UB_13 0.0024391000 _diffrn_orient_matrix_UB_21 -0.0114554000 _diffrn_orient_matrix_UB_22 -0.0201318000 _diffrn_orient_matrix_UB_23 -0.0425256000 _diffrn_orient_matrix_UB_31 -0.0074701000 _diffrn_orient_matrix_UB_32 0.0299479000 _diffrn_orient_matrix_UB_33 -0.0285526000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0405 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.894 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 12574 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.894 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.705 _diffrn_reflns_theta_min 2.544 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.382 _exptl_crystal_description prism _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.379 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 6185 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0570 _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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1497 _refine_ls_wR_factor_ref 0.1744 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4364 _reflns_number_total 6185 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02501a2.cif _cod_data_source_block as-tubc _cod_depositor_comments 'Adding full bibliography for 7240597.cif.' _cod_database_code 7240597 _shelx_shelxl_version_number 2018/1 _chemical_oxdiff_formula 'C21 H16 S1 N4 O1' _chemical_oxdiff_usercomment 'Saeed's AS-TUBC' _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_max 0.977 _shelx_estimated_absorpt_t_min 0.901 _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.44 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All O(H,H) groups 2.a Free rotating group: O1W(H1WA,H1WB) 2.b Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), N4(H4), C4(H4A), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20) ; _shelx_res_file ; TITL as-tubc_a.res in P2(1)/n as-tubc.res created by SHELXL-2018/1 at 15:36:52 on 02-Aug-2018 REM Old TITL AS-TUBC in P21/n #14 REM SHELXT solution in P2(1)/n REM R1 0.193, Rweak 0.033, Alpha 0.029, Orientation as input REM Formula found by SHELXT: C21 N4 O2 S CELL 0.71073 6.9104 19.6432 14.0505 90 100.235 90 ZERR 4 0.0003 0.0007 0.0005 0 0.004 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 84 72 16 8 4 EQIV $1 1-X,1-Y,1-Z EQIV $2 -0.5+X,0.5-Y,-0.5+Z EQIV $3 0.5-X,-0.5+Y,1.5-Z L.S. 50 PLAN 10 SIZE 0.54 0.14 0.12 TEMP -100(2) HTAB N1 O1W_$1 HTAB N2 O1 HTAB N4 O1W_$2 HTAB C4 O1W_$1 HTAB C10 S1 HTAB C20 O1_$3 HTAB O1W S1_$1 HTAB O1W N3 BOND $H list 4 CONF fmap 2 acta OMIT 1 2 3 OMIT -2 7 5 OMIT 1 4 1 OMIT 0 1 4 OMIT 1 9 4 OMIT -1 6 7 REM REM REM WGHT 0.100000 FVAR 0.25132 S1 5 0.247008 0.557207 0.260191 11.00000 0.09110 0.03049 = 0.02332 0.00142 0.00013 -0.01674 O1 4 0.276626 0.669055 0.545416 11.00000 0.06117 0.02956 = 0.03589 0.00056 0.01774 0.00227 N1 3 0.258823 0.658597 0.382901 11.00000 0.03968 0.02267 = 0.03272 0.00367 0.00361 -0.00202 AFIX 43 H1 2 0.254256 0.682553 0.329623 11.00000 -1.20000 AFIX 0 N2 3 0.243601 0.553818 0.451926 11.00000 0.03801 0.02126 = 0.02754 0.00171 0.00766 0.00062 AFIX 43 H2 2 0.244565 0.579698 0.503131 11.00000 -1.20000 AFIX 0 N3 3 0.266207 0.255698 0.649927 11.00000 0.03744 0.02492 = 0.02019 0.00127 0.00252 0.00137 N4 3 0.170822 0.224329 0.496141 11.00000 0.02986 0.02308 = 0.01749 0.00205 0.00290 0.00037 AFIX 43 H4 2 0.135392 0.227773 0.432999 11.00000 -1.20000 AFIX 0 C1 1 0.248431 0.588314 0.370406 11.00000 0.03288 0.02477 = 0.02892 0.00387 0.00019 -0.00321 C2 1 0.275230 0.695862 0.466839 11.00000 0.03023 0.02563 = 0.03733 0.00125 0.00971 0.00131 C3 1 0.291776 0.770945 0.456609 11.00000 0.02727 0.02551 = 0.04587 0.00080 0.01327 0.00276 C4 1 0.241657 0.804447 0.368649 11.00000 0.04764 0.02729 = 0.05030 0.00484 0.02414 0.00536 AFIX 43 H4A 2 0.193726 0.779442 0.311438 11.00000 -1.20000 AFIX 0 C5 1 0.261985 0.874855 0.364701 11.00000 0.05457 0.02997 = 0.07121 0.01066 0.03448 0.00813 AFIX 43 H5 2 0.227724 0.898071 0.304759 11.00000 -1.20000 AFIX 0 C6 1 0.331645 0.910646 0.447619 11.00000 0.04385 0.02517 = 0.09204 -0.00335 0.02827 0.00059 AFIX 43 H6 2 0.346914 0.958616 0.444545 11.00000 -1.20000 AFIX 0 C7 1 0.379402 0.877952 0.534775 11.00000 0.04007 0.03386 = 0.08459 -0.01749 0.00243 -0.00036 AFIX 43 H7 2 0.427219 0.903286 0.591694 11.00000 -1.20000 AFIX 0 C8 1 0.357973 0.807755 0.540018 11.00000 0.03734 0.03321 = 0.05679 -0.00554 0.00054 0.00260 AFIX 43 H8 2 0.388640 0.785152 0.600600 11.00000 -1.20000 AFIX 0 C9 1 0.237246 0.483484 0.470626 11.00000 0.02893 0.02113 = 0.02668 0.00151 0.00608 0.00041 C10 1 0.201047 0.432497 0.402167 11.00000 0.06751 0.02608 = 0.02169 0.00118 0.00533 -0.00537 AFIX 43 H10 2 0.178357 0.443455 0.335252 11.00000 -1.20000 AFIX 0 C11 1 0.197998 0.365354 0.431554 11.00000 0.06106 0.02432 = 0.02098 -0.00114 0.00544 -0.00547 AFIX 43 H11 2 0.177153 0.330515 0.383935 11.00000 -1.20000 AFIX 0 C12 1 0.224410 0.347415 0.528262 11.00000 0.02680 0.02248 = 0.02121 0.00098 0.00288 0.00217 C13 1 0.255736 0.399479 0.596278 11.00000 0.04656 0.02562 = 0.02045 0.00099 0.00418 0.00354 AFIX 43 H13 2 0.271752 0.388841 0.663178 11.00000 -1.20000 AFIX 0 C14 1 0.263759 0.466091 0.567760 11.00000 0.04712 0.02326 = 0.02330 -0.00136 0.00607 0.00442 AFIX 43 H14 2 0.287883 0.500882 0.615359 11.00000 -1.20000 AFIX 0 C15 1 0.220402 0.276620 0.559216 11.00000 0.02618 0.02307 = 0.01938 0.00026 0.00355 0.00179 C16 1 0.186156 0.165273 0.548949 11.00000 0.02651 0.02410 = 0.02248 0.00347 0.00531 0.00213 C17 1 0.156291 0.097519 0.521982 11.00000 0.03534 0.02375 = 0.02964 -0.00015 0.00768 -0.00172 AFIX 43 H17 2 0.116050 0.084539 0.456312 11.00000 -1.20000 AFIX 0 C18 1 0.188073 0.050049 0.595465 11.00000 0.04523 0.02492 = 0.04226 0.00552 0.01280 -0.00029 AFIX 43 H18 2 0.168833 0.003143 0.580199 11.00000 -1.20000 AFIX 0 C19 1 0.247832 0.069442 0.691664 11.00000 0.05850 0.03101 = 0.03348 0.01302 0.01078 0.00351 AFIX 43 H19 2 0.269762 0.035279 0.740246 11.00000 -1.20000 AFIX 0 C20 1 0.276073 0.136892 0.718378 11.00000 0.05391 0.03605 = 0.02498 0.00893 0.00514 0.00059 AFIX 43 H20 2 0.314656 0.149623 0.784248 11.00000 -1.20000 AFIX 0 C21 1 0.245906 0.185441 0.645235 11.00000 0.03307 0.02549 = 0.02221 0.00325 0.00534 0.00233 AFIX 6 O1W 4 0.572678 0.295915 0.795342 11.00000 0.06338 0.03044 = 0.02225 0.00192 -0.00209 -0.00855 H1WA 2 0.589380 0.339715 0.792197 11.00000 -1.50000 H1WB 2 0.460830 0.288304 0.757452 11.00000 -1.50000 AFIX 0 HKLF 4 REM as-tubc_a.res in P2(1)/n REM R1 = 0.0570 for 4364 Fo > 4sig(Fo) and 0.0856 for all 6185 data REM 256 parameters refined using 0 restraints END WGHT 0.0734 0.3236 REM Highest difference peak 0.379, deepest hole -0.408, 1-sigma level 0.058 Q1 1 0.2487 0.4722 0.5156 11.00000 0.05 0.38 Q2 1 0.2053 0.4592 0.4378 11.00000 0.05 0.36 Q3 1 0.2371 0.1720 0.5974 11.00000 0.05 0.35 Q4 1 0.2222 0.3763 0.5596 11.00000 0.05 0.34 Q5 1 0.1809 0.3996 0.4233 11.00000 0.05 0.33 Q6 1 0.2678 0.2221 0.6455 11.00000 0.05 0.31 Q7 1 0.1751 0.2523 0.5275 11.00000 0.05 0.31 Q8 1 0.2662 0.1606 0.6786 11.00000 0.05 0.30 Q9 1 0.1373 0.5699 0.2816 11.00000 0.05 0.30 Q10 1 0.2180 0.1013 0.7171 11.00000 0.05 0.29 ; _shelx_res_checksum 5598 _olex2_exptl_crystal_mounting_method 'POLYMER LOOP' _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.357 _oxdiff_exptl_absorpt_empirical_full_min 0.632 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 S1 S 0.24701(9) 0.55721(2) 0.26019(3) 0.04953(18) Uani 1 1 d . . . . . O1 O 0.2766(2) 0.66905(6) 0.54542(9) 0.0411(3) Uani 1 1 d . . . . . N1 N 0.2588(2) 0.65860(6) 0.38290(10) 0.0320(3) Uani 1 1 d . . . . . H1 H 0.254256 0.682553 0.329623 0.038 Uiso 1 1 calc R . . . . N2 N 0.2436(2) 0.55382(6) 0.45193(10) 0.0287(3) Uani 1 1 d . . . . . H2 H 0.244565 0.579698 0.503131 0.034 Uiso 1 1 calc R . . . . N3 N 0.2662(2) 0.25570(6) 0.64993(9) 0.0278(3) Uani 1 1 d . . . . . N4 N 0.17082(19) 0.22433(6) 0.49614(8) 0.0236(3) Uani 1 1 d . . . . . H4 H 0.135392 0.227773 0.432999 0.028 Uiso 1 1 calc R . . . . C1 C 0.2484(2) 0.58831(8) 0.37041(11) 0.0295(3) Uani 1 1 d . . . . . C2 C 0.2752(2) 0.69586(8) 0.46684(12) 0.0306(3) Uani 1 1 d . . . . . C3 C 0.2918(2) 0.77095(8) 0.45661(13) 0.0321(3) Uani 1 1 d . . . . . C4 C 0.2417(3) 0.80445(8) 0.36865(15) 0.0399(4) Uani 1 1 d . . . . . H4A H 0.193726 0.779442 0.311438 0.048 Uiso 1 1 calc R . . . . C5 C 0.2620(3) 0.87486(9) 0.36470(18) 0.0491(5) Uani 1 1 d . . . . . H5 H 0.227724 0.898071 0.304759 0.059 Uiso 1 1 calc R . . . . C6 C 0.3316(3) 0.91065(9) 0.44762(19) 0.0517(5) Uani 1 1 d . . . . . H6 H 0.346914 0.958616 0.444545 0.062 Uiso 1 1 calc R . . . . C7 C 0.3794(3) 0.87795(10) 0.53478(19) 0.0539(6) Uani 1 1 d . . . . . H7 H 0.427219 0.903286 0.591694 0.065 Uiso 1 1 calc R . . . . C8 C 0.3580(3) 0.80776(9) 0.54002(16) 0.0434(4) Uani 1 1 d . . . . . H8 H 0.388640 0.785152 0.600600 0.052 Uiso 1 1 calc R . . . . C9 C 0.2372(2) 0.48348(7) 0.47063(10) 0.0254(3) Uani 1 1 d . . . . . C10 C 0.2010(3) 0.43250(8) 0.40217(12) 0.0387(4) Uani 1 1 d . . . . . H10 H 0.178357 0.443455 0.335252 0.046 Uiso 1 1 calc R . . . . C11 C 0.1980(3) 0.36535(8) 0.43155(11) 0.0357(4) Uani 1 1 d . . . . . H11 H 0.177153 0.330515 0.383935 0.043 Uiso 1 1 calc R . . . . C12 C 0.2244(2) 0.34741(7) 0.52826(10) 0.0237(3) Uani 1 1 d . . . . . C13 C 0.2557(3) 0.39948(8) 0.59628(11) 0.0311(3) Uani 1 1 d . . . . . H13 H 0.271752 0.388841 0.663178 0.037 Uiso 1 1 calc R . . . . C14 C 0.2638(3) 0.46609(8) 0.56776(11) 0.0313(3) Uani 1 1 d . . . . . H14 H 0.287883 0.500882 0.615359 0.038 Uiso 1 1 calc R . . . . C15 C 0.2204(2) 0.27662(7) 0.55922(10) 0.0229(3) Uani 1 1 d . . . . . C16 C 0.1862(2) 0.16527(7) 0.54895(10) 0.0242(3) Uani 1 1 d . . . . . C17 C 0.1563(2) 0.09752(7) 0.52198(11) 0.0293(3) Uani 1 1 d . . . . . H17 H 0.116050 0.084539 0.456312 0.035 Uiso 1 1 calc R . . . . C18 C 0.1881(3) 0.05005(8) 0.59546(13) 0.0369(4) Uani 1 1 d . . . . . H18 H 0.168833 0.003143 0.580199 0.044 Uiso 1 1 calc R . . . . C19 C 0.2478(3) 0.06944(9) 0.69166(13) 0.0407(4) Uani 1 1 d . . . . . H19 H 0.269762 0.035279 0.740246 0.049 Uiso 1 1 calc R . . . . C20 C 0.2761(3) 0.13689(9) 0.71838(12) 0.0385(4) Uani 1 1 d . . . . . H20 H 0.314656 0.149623 0.784248 0.046 Uiso 1 1 calc R . . . . C21 C 0.2459(2) 0.18544(7) 0.64524(10) 0.0269(3) Uani 1 1 d . . . . . O1W O 0.5727(2) 0.29592(6) 0.79534(8) 0.0399(3) Uani 1 1 d . . . . . H1WA H 0.589380 0.339715 0.792197 0.060 Uiso 1 1 d G . . . . H1WB H 0.460830 0.288304 0.757452 0.060 Uiso 1 1 d G . . . . 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 0.0911(4) 0.0305(2) 0.0233(2) 0.00142(15) 0.0001(2) -0.0167(2) O1 0.0612(9) 0.0296(6) 0.0359(7) 0.0006(5) 0.0177(6) 0.0023(5) N1 0.0397(8) 0.0227(6) 0.0327(7) 0.0037(5) 0.0036(5) -0.0020(5) N2 0.0380(8) 0.0213(6) 0.0275(6) 0.0017(5) 0.0077(5) 0.0006(5) N3 0.0374(7) 0.0249(6) 0.0202(5) 0.0013(4) 0.0025(5) 0.0014(5) N4 0.0299(6) 0.0231(6) 0.0175(5) 0.0021(4) 0.0029(4) 0.0004(5) C1 0.0329(8) 0.0248(7) 0.0289(7) 0.0039(6) 0.0002(6) -0.0032(6) C2 0.0302(8) 0.0256(7) 0.0373(8) 0.0012(6) 0.0097(6) 0.0013(6) C3 0.0273(8) 0.0255(7) 0.0459(9) 0.0008(6) 0.0133(7) 0.0028(6) C4 0.0476(11) 0.0273(8) 0.0503(10) 0.0048(7) 0.0241(8) 0.0054(7) C5 0.0546(12) 0.0300(8) 0.0712(14) 0.0107(9) 0.0345(11) 0.0081(8) C6 0.0439(11) 0.0252(8) 0.0920(17) -0.0034(9) 0.0283(11) 0.0006(8) C7 0.0401(11) 0.0339(9) 0.0846(17) -0.0175(10) 0.0024(10) -0.0004(8) C8 0.0373(10) 0.0332(9) 0.0568(12) -0.0055(8) 0.0005(8) 0.0026(7) C9 0.0289(8) 0.0211(6) 0.0267(7) 0.0015(5) 0.0061(5) 0.0004(5) C10 0.0675(13) 0.0261(7) 0.0217(7) 0.0012(6) 0.0053(7) -0.0054(7) C11 0.0611(12) 0.0243(7) 0.0210(7) -0.0011(5) 0.0054(7) -0.0055(7) C12 0.0268(7) 0.0225(6) 0.0212(6) 0.0010(5) 0.0029(5) 0.0022(5) C13 0.0466(10) 0.0256(7) 0.0205(6) 0.0010(5) 0.0042(6) 0.0035(6) C14 0.0471(10) 0.0233(7) 0.0233(7) -0.0014(5) 0.0061(6) 0.0044(6) C15 0.0262(7) 0.0231(6) 0.0194(6) 0.0003(5) 0.0035(5) 0.0018(5) C16 0.0265(7) 0.0241(7) 0.0225(6) 0.0035(5) 0.0053(5) 0.0021(5) C17 0.0353(9) 0.0238(7) 0.0296(7) -0.0002(5) 0.0077(6) -0.0017(6) C18 0.0452(10) 0.0249(7) 0.0423(9) 0.0055(6) 0.0128(7) -0.0003(7) C19 0.0585(12) 0.0310(8) 0.0335(9) 0.0130(7) 0.0108(8) 0.0035(8) C20 0.0539(11) 0.0361(9) 0.0250(7) 0.0089(6) 0.0051(7) 0.0006(7) C21 0.0331(8) 0.0255(7) 0.0222(6) 0.0033(5) 0.0053(5) 0.0023(6) O1W 0.0634(9) 0.0304(6) 0.0223(5) 0.0019(4) -0.0021(5) -0.0085(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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1 115.5 . . ? C2 N1 H1 115.5 . . ? C2 N1 C1 129.09(14) . . ? C1 N2 H2 114.2 . . ? C1 N2 C9 131.58(13) . . ? C9 N2 H2 114.2 . . ? C15 N3 C21 104.97(12) . . ? C15 N4 H4 126.3 . . ? C15 N4 C16 107.46(12) . . ? C16 N4 H4 126.3 . . ? N1 C1 S1 118.26(12) . . ? N2 C1 S1 127.94(12) . . ? N2 C1 N1 113.79(14) . . ? O1 C2 N1 122.12(14) . . ? O1 C2 C3 121.74(15) . . ? N1 C2 C3 116.14(14) . . ? C4 C3 C2 122.98(16) . . ? C8 C3 C2 117.10(16) . . ? C8 C3 C4 119.92(16) . . ? C3 C4 H4A 120.2 . . ? C3 C4 C5 119.69(19) . . ? C5 C4 H4A 120.2 . . ? C4 C5 H5 120.1 . . ? C6 C5 C4 119.8(2) . . ? C6 C5 H5 120.1 . . ? C5 C6 H6 119.6 . . ? C7 C6 C5 120.73(18) . . ? C7 C6 H6 119.6 . . ? C6 C7 H7 120.0 . . ? C6 C7 C8 120.1(2) . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 119.7(2) . . ? C3 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 N2 126.12(13) . . ? C10 C9 C14 118.87(13) . . ? C14 C9 N2 114.97(13) . . ? C9 C10 H10 120.2 . . ? C9 C10 C11 119.62(15) . . ? C11 C10 H10 120.2 . . ? C10 C11 H11 119.0 . . ? C10 C11 C12 121.97(15) . . ? C12 C11 H11 119.0 . . ? C11 C12 C13 117.70(13) . . ? C11 C12 C15 121.95(13) . . ? C13 C12 C15 120.35(13) . . ? C12 C13 H13 119.7 . . ? C14 C13 C12 120.67(14) . . ? C14 C13 H13 119.7 . . ? C9 C14 H14 119.4 . . ? C13 C14 C9 121.13(14) . . ? C13 C14 H14 119.4 . . ? N3 C15 N4 112.49(12) . . ? N3 C15 C12 124.71(13) . . ? N4 C15 C12 122.79(12) . . ? N4 C16 C17 132.04(13) . . ? N4 C16 C21 105.35(12) . . ? C17 C16 C21 122.60(13) . . ? C16 C17 H17 121.7 . . ? C18 C17 C16 116.57(15) . . ? C18 C17 H17 121.7 . . ? C17 C18 H18 119.3 . . ? C17 C18 C19 121.41(15) . . ? C19 C18 H18 119.3 . . ? C18 C19 H19 119.0 . . ? C20 C19 C18 121.91(15) . . ? C20 C19 H19 119.0 . . ? C19 C20 H20 121.3 . . ? C19 C20 C21 117.49(16) . . ? C21 C20 H20 121.3 . . ? N3 C21 C16 109.72(12) . . ? N3 C21 C20 130.28(14) . . ? C20 C21 C16 120.00(14) . . ? H1WA O1W H1WB 104.5 . . ? 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 S1 C1 1.6632(17) . ? O1 C2 1.2217(19) . ? N1 H1 0.8800 . ? N1 C1 1.3919(19) . ? N1 C2 1.376(2) . ? N2 H2 0.8800 . ? N2 C1 1.336(2) . ? N2 C9 1.4085(18) . ? N3 C15 1.3229(17) . ? N3 C21 1.388(2) . ? N4 H4 0.8800 . ? N4 C15 1.3601(18) . ? N4 C16 1.3710(18) . ? C2 C3 1.488(2) . ? C3 C4 1.389(3) . ? C3 C8 1.384(3) . ? C4 H4A 0.9500 . ? C4 C5 1.392(2) . ? C5 H5 0.9500 . ? C5 C6 1.373(3) . ? C6 H6 0.9500 . ? C6 C7 1.370(3) . ? C7 H7 0.9500 . ? C7 C8 1.390(3) . ? C8 H8 0.9500 . ? C9 C10 1.380(2) . ? C9 C14 1.387(2) . ? C10 H10 0.9500 . ? C10 C11 1.383(2) . ? C11 H11 0.9500 . ? C11 C12 1.384(2) . ? C12 C13 1.390(2) . ? C12 C15 1.4588(19) . ? C13 H13 0.9500 . ? C13 C14 1.372(2) . ? C14 H14 0.9500 . ? C16 C17 1.389(2) . ? C16 C21 1.400(2) . ? C17 H17 0.9500 . ? C17 C18 1.380(2) . ? C18 H18 0.9500 . ? C18 C19 1.394(3) . ? C19 H19 0.9500 . ? C19 C20 1.381(2) . ? C20 H20 0.9500 . ? C20 C21 1.390(2) . ? O1W H1WA 0.8702 . ? O1W H1WB 0.8700 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 O1W 0.88 2.33 3.0761(19) 142.4 3_666 yes N2 H2 O1 0.88 1.85 2.6067(17) 142.4 . yes N4 H4 O1W 0.88 1.96 2.8103(16) 161.6 4_565 yes C4 H4A O1W 0.95 2.81 3.449(2) 125.2 3_666 yes C10 H10 S1 0.95 2.55 3.2104(17) 126.7 . yes C20 H20 O1 0.95 2.61 3.461(2) 149.4 2_546 yes O1W H1WA S1 0.87 2.49 3.2911(13) 152.8 3_666 yes O1W H1WB N3 0.87 1.94 2.7832(17) 161.6 . yes 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 O1 C2 C3 C4 -163.18(17) . . . . ? O1 C2 C3 C8 15.9(2) . . . . ? N1 C2 C3 C4 17.0(2) . . . . ? N1 C2 C3 C8 -163.93(16) . . . . ? N2 C9 C10 C11 -179.53(16) . . . . ? N2 C9 C14 C13 178.22(15) . . . . ? N4 C16 C17 C18 179.16(16) . . . . ? N4 C16 C21 N3 -0.05(17) . . . . ? N4 C16 C21 C20 -179.78(15) . . . . ? C1 N1 C2 O1 -2.4(3) . . . . ? C1 N1 C2 C3 177.42(15) . . . . ? C1 N2 C9 C10 -11.8(3) . . . . ? C1 N2 C9 C14 170.60(17) . . . . ? C2 N1 C1 S1 -175.18(14) . . . . ? C2 N1 C1 N2 3.9(2) . . . . ? C2 C3 C4 C5 -179.70(16) . . . . ? C2 C3 C8 C7 178.99(18) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C3 C8 C7 -1.9(3) . . . . ? C4 C5 C6 C7 -0.8(3) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? C6 C7 C8 C3 1.2(3) . . . . ? C8 C3 C4 C5 1.2(3) . . . . ? C9 N2 C1 S1 0.4(3) . . . . ? C9 N2 C1 N1 -178.54(15) . . . . ? C9 C10 C11 C12 2.0(3) . . . . ? C10 C9 C14 C13 0.4(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C10 C11 C12 C15 179.75(16) . . . . ? C11 C12 C13 C14 -1.2(2) . . . . ? C11 C12 C15 N3 172.05(16) . . . . ? C11 C12 C15 N4 -7.0(2) . . . . ? C12 C13 C14 C9 1.2(3) . . . . ? C13 C12 C15 N3 -7.8(2) . . . . ? C13 C12 C15 N4 173.16(15) . . . . ? C14 C9 C10 C11 -2.0(3) . . . . ? C15 N3 C21 C16 -0.14(17) . . . . ? C15 N3 C21 C20 179.56(18) . . . . ? C15 N4 C16 C17 -178.90(16) . . . . ? C15 N4 C16 C21 0.22(16) . . . . ? C15 C12 C13 C14 178.64(15) . . . . ? C16 N4 C15 N3 -0.33(17) . . . . ? C16 N4 C15 C12 178.79(13) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? C17 C16 C21 N3 179.18(14) . . . . ? C17 C16 C21 C20 -0.6(2) . . . . ? C17 C18 C19 C20 0.7(3) . . . . ? C18 C19 C20 C21 -1.1(3) . . . . ? C19 C20 C21 N3 -178.69(17) . . . . ? C19 C20 C21 C16 1.0(3) . . . . ? C21 N3 C15 N4 0.29(17) . . . . ? C21 N3 C15 C12 -178.81(14) . . . . ? C21 C16 C17 C18 0.2(2) . . . . ?