#------------------------------------------------------------------------------ #$Date: 2026-06-11 23:56:06 +0100 (Thu, 11 Jun 2026) $ #$Revision: 306554 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/11/7721112.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_7721112 loop_ _publ_author_name 'Manimuthu, Akilesh' 'Bhuvanesh, Nattamai' 'Nallasamy, Professor Dr. Dharmaraj' _publ_section_title ; Organoruthenium(II) complexes appended with racemic pyrazoline ligands: An integrated experimental and theoretical insights revealing their apoptotic efficacy ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D6DT00737F _journal_year 2026 _chemical_formula_moiety 'C17 H17 N3 O S' _chemical_formula_sum 'C17 H17 N3 O S' _chemical_formula_weight 311.39 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-06-26 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _audit_update_record ; 2024-06-29 deposited with the CCDC. 2026-06-11 downloaded from the CCDC. ; _cell_angle_alpha 72.660(2) _cell_angle_beta 82.131(2) _cell_angle_gamma 87.333(2) _cell_formula_units_Z 2 _cell_length_a 5.64080(10) _cell_length_b 9.3444(3) _cell_length_c 15.6537(4) _cell_measurement_reflns_used 13771 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 79.0760 _cell_measurement_theta_min 2.9440 _cell_volume 780.18(4) _computing_cell_refinement 'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))' _computing_data_reduction 'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/1 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _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 -49.00 -20.00 0.50 0.10 -- -91.75 45.00 90.00 58 2 \w -12.00 28.00 0.50 0.05 -- -47.44 19.00 30.00 80 3 \w -12.00 28.00 0.50 0.05 -- -47.44 19.00 0.00 80 4 \w -49.00 -20.00 0.50 0.10 -- -91.75 45.00 0.00 58 5 \w -39.00 26.00 0.50 0.05 -- -47.44 38.00-120.00 130 6 \w 34.00 93.00 0.50 0.05 -- 47.44-125.00 60.00 118 7 \w 44.00 111.00 0.50 0.10 -- 113.25-125.00 120.00 134 8 \w 44.00 111.00 0.50 0.10 -- 113.25-125.00 120.00 134 9 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00 90.00 128 10 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00 30.00 128 11 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00 0.00 128 12 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00 -90.00 128 13 \w 43.00 107.00 0.50 0.10 -- 113.25-104.00-134.00 128 14 \w 44.00 111.00 0.50 0.10 -- 113.25-125.00-180.00 134 15 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00-180.00 128 16 \w 18.00 83.00 0.50 0.05 -- 47.44-104.00-134.00 130 17 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00 -30.00 128 18 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00 60.00 128 19 \w 42.00 106.00 0.50 0.10 -- 113.25 -95.00 90.00 128 20 \w 42.00 75.00 0.50 0.10 -- 113.25 -61.00 120.00 66 21 \w 42.00 75.00 0.50 0.10 -- 113.25 -61.00 150.00 66 22 \w 42.00 75.00 0.50 0.10 -- 113.25 -61.00 90.00 66 23 \w 42.00 75.00 0.50 0.10 -- 113.25 -61.00 60.00 66 24 \w 42.00 75.00 0.50 0.10 -- 113.25 -61.00 0.00 66 25 \w 42.00 75.00 0.50 0.10 -- 113.25 -61.00 -60.00 66 26 \w 42.00 136.00 0.50 0.10 -- 113.25 -77.00-150.00 188 27 \w 42.00 75.00 0.50 0.10 -- 113.25 -61.00-150.00 66 28 \w 100.00 176.00 0.50 0.10 -- 113.25 15.00-120.00 152 29 \w 101.00 178.00 0.50 0.10 -- 113.25 45.00 -60.00 154 30 \w 101.00 178.00 0.50 0.10 -- 113.25 45.00 -60.00 154 31 \w 101.00 178.00 0.50 0.10 -- 113.25 30.00-120.00 154 32 \w 101.00 178.00 0.50 0.10 -- 113.25 30.00-120.00 154 33 \w 110.00 178.00 0.50 0.10 -- 113.25 77.00 -90.00 136 34 \w 100.00 176.00 0.50 0.10 -- 113.25 15.00 0.00 152 35 \w 110.00 178.00 0.50 0.10 -- 113.25 77.00 60.00 136 36 \w 101.00 178.00 0.50 0.10 -- 113.25 45.00 30.00 154 37 \w 106.00 178.00 0.50 0.10 -- 113.25 104.00 -33.00 144 38 \w -27.00 12.00 0.50 0.05 -- 47.44 -19.00 150.00 78 39 \w -27.00 12.00 0.50 0.05 -- 47.44 -19.00-180.00 78 40 \w -27.00 12.00 0.50 0.05 -- 47.44 -19.00-150.00 78 41 \w -82.00 3.00 0.50 0.05 -- -47.44 104.00 -33.00 170 42 \w -82.00 3.00 0.50 0.05 -- -47.44 104.00 -33.00 170 43 \w -81.00 -21.00 0.50 0.10 -- -91.75 104.00 -33.00 120 44 \w -120.00 -35.00 0.50 0.05 -- -47.44 -38.00 90.00 170 45 \w -163.00-110.00 0.50 0.10 -- -91.75 -77.00 120.00 106 46 \w -163.00-106.00 0.50 0.10 -- -91.75 -61.00 -30.00 114 47 \w -163.00 -93.00 0.50 0.10 -- -91.75 -50.00 -64.22 140 48 \w -120.00 -35.00 0.50 0.05 -- -47.44 -38.00-120.00 170 49 \w -162.00 -84.00 0.50 0.10 -- -91.75-104.00-134.00 156 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.2749760000 _diffrn_orient_matrix_UB_12 0.0136385000 _diffrn_orient_matrix_UB_13 0.0110647000 _diffrn_orient_matrix_UB_21 0.0113821000 _diffrn_orient_matrix_UB_22 0.0959774000 _diffrn_orient_matrix_UB_23 -0.0993406000 _diffrn_orient_matrix_UB_31 -0.0165741000 _diffrn_orient_matrix_UB_32 -0.1429466000 _diffrn_orient_matrix_UB_33 -0.0286143000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_unetI/netI 0.0129 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 15758 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.501 _diffrn_reflns_theta_min 2.982 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current '1 mA' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _diffrn_source_voltage '50 kV' _exptl_absorpt_coefficient_mu 1.880 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.119 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.326 _exptl_crystal_description block _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.649 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.225 _refine_diff_density_max 0.312 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef 0.0045(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/1 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 3171 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0302 _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^)+(0.0308P)^2^+0.4373P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.0747 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3157 _reflns_number_total 3171 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00737f1.cif _cod_data_source_block nd_c2s1 _cod_database_code 7721112 _shelx_shelxl_version_number 2019/1 _chemical_oxdiff_formula CHNOS _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 0.677 _shelx_estimated_absorpt_t_min 0.375 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C10(H10) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16) 2.d X=CH2 refined with riding coordinates: N3(H3A,H3B) 2.e Idealised Me refined as rotating group: C17(H17A,H17B,H17C) ; _shelx_res_file ; TITL nd_c2s1_a.res in P-1 nd_c2s1.res created by SHELXL-2019/1 at 15:49:45 on 26-Jun-2024 REM Old TITL ND_C2S1 in P-1 REM SHELXT solution in P-1: R1 0.098, Rweak 0.007, Alpha 0.031 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N2 O2 S CELL 1.54184 5.6408 9.3444 15.6537 72.66 82.131 87.333 ZERR 2 0.0001 0.0003 0.0004 0.002 0.002 0.002 LATT 1 SFAC C H N O S UNIT 34 34 6 2 2 L.S. 8 PLAN 10 SIZE 0.225 0.58 0.649 TEMP -173.15(10) CONF BOND list 4 MORE -1 BOND $H wpdb -1 fmap 2 53 acta SHEL 999 0.8 OMIT -1 5 3 REM REM REM WGHT 0.030800 0.437300 EXTI 0.004499 FVAR 13.41664 S1 5 -0.157053 0.786383 0.098055 11.00000 0.02069 0.02018 = 0.01488 -0.00076 -0.00548 -0.00677 O1 4 0.485680 0.181488 0.152186 11.00000 0.02524 0.01775 = 0.02578 -0.01085 0.00357 -0.00270 N1 3 0.069603 0.782984 0.236035 11.00000 0.01926 0.01277 = 0.01338 -0.00286 -0.00421 -0.00263 N2 3 0.237176 0.839398 0.274397 11.00000 0.01769 0.01499 = 0.01486 -0.00554 -0.00362 -0.00056 N3 3 0.169178 0.975743 0.108486 11.00000 0.02355 0.01680 = 0.01428 -0.00116 -0.00590 -0.00504 AFIX 93 H3A 2 0.266937 1.006554 0.138516 11.00000 -1.20000 H3B 2 0.157451 1.026087 0.051927 11.00000 -1.20000 AFIX 0 C1 1 0.039232 0.853164 0.148554 11.00000 0.01685 0.01429 = 0.01405 -0.00415 -0.00170 0.00128 C2 1 0.247827 0.751652 0.354692 11.00000 0.01731 0.01390 = 0.01391 -0.00502 -0.00135 0.00116 C3 1 0.413786 0.783769 0.410961 11.00000 0.01829 0.01504 = 0.01557 -0.00670 -0.00384 0.00301 C4 1 0.582440 0.898861 0.373474 11.00000 0.02061 0.01716 = 0.01818 -0.00527 -0.00311 0.00061 AFIX 43 H4 2 0.589590 0.955323 0.311690 11.00000 -1.20000 AFIX 0 C5 1 0.738440 0.930052 0.426630 11.00000 0.02105 0.02023 = 0.02513 -0.00831 -0.00433 -0.00212 AFIX 43 H5 2 0.852448 1.007895 0.401023 11.00000 -1.20000 AFIX 0 C6 1 0.729315 0.848189 0.517236 11.00000 0.02071 0.02477 = 0.02360 -0.01268 -0.00818 0.00307 AFIX 43 H6 2 0.836599 0.870361 0.553287 11.00000 -1.20000 AFIX 0 C7 1 0.563468 0.734164 0.554911 11.00000 0.02193 0.02308 = 0.01611 -0.00742 -0.00493 0.00532 AFIX 43 H7 2 0.556795 0.678439 0.616810 11.00000 -1.20000 AFIX 0 C8 1 0.406786 0.701474 0.501903 11.00000 0.01968 0.01726 = 0.01638 -0.00527 -0.00201 0.00070 AFIX 43 H8 2 0.294416 0.622732 0.527719 11.00000 -1.20000 AFIX 0 C9 1 0.072333 0.623715 0.381495 11.00000 0.01942 0.01442 = 0.01187 -0.00304 -0.00156 -0.00057 AFIX 23 H9A 2 -0.066138 0.640767 0.423608 11.00000 -1.20000 H9B 2 0.149727 0.526966 0.409580 11.00000 -1.20000 AFIX 0 C10 1 -0.003448 0.628506 0.289168 11.00000 0.01656 0.01335 = 0.01236 -0.00147 -0.00203 -0.00184 AFIX 13 H10 2 -0.180559 0.616729 0.294175 11.00000 -1.20000 AFIX 0 C11 1 0.128499 0.512534 0.249895 11.00000 0.01728 0.01521 = 0.01132 -0.00350 -0.00395 -0.00072 C12 1 0.352029 0.542573 0.199003 11.00000 0.01812 0.01474 = 0.01958 -0.00461 -0.00160 -0.00370 AFIX 43 H12 2 0.420911 0.638505 0.187148 11.00000 -1.20000 AFIX 0 C13 1 0.477481 0.435416 0.164964 11.00000 0.01701 0.01906 = 0.01932 -0.00581 0.00034 -0.00288 AFIX 43 H13 2 0.629593 0.458351 0.129810 11.00000 -1.20000 AFIX 0 C14 1 0.378146 0.294505 0.182881 11.00000 0.02126 0.01660 = 0.01555 -0.00690 -0.00314 0.00102 C15 1 0.155748 0.261588 0.235359 11.00000 0.02441 0.01572 = 0.01782 -0.00546 -0.00109 -0.00637 AFIX 43 H15 2 0.088915 0.164717 0.248740 11.00000 -1.20000 AFIX 0 C16 1 0.032385 0.370078 0.267950 11.00000 0.01860 0.01894 = 0.01405 -0.00494 0.00054 -0.00531 AFIX 43 H16 2 -0.119767 0.347197 0.303080 11.00000 -1.20000 AFIX 0 C17 1 0.677419 0.221831 0.079249 11.00000 0.02421 0.02505 = 0.02775 -0.01227 0.00504 0.00125 AFIX 137 H17A 2 0.625582 0.304623 0.030172 11.00000 -1.50000 H17B 2 0.721542 0.135237 0.057179 11.00000 -1.50000 H17C 2 0.816093 0.253187 0.100580 11.00000 -1.50000 AFIX 0 HKLF 4 REM nd_c2s1_a.res in P-1 REM wR2 = 0.0747, GooF = S = 1.054, Restrained GooF = 1.054 for all data REM R1 = 0.0302 for 3157 Fo > 4sig(Fo) and 0.0303 for all 3171 data REM 201 parameters refined using 0 restraints END WGHT 0.0308 0.4372 REM Highest difference peak 0.312, deepest hole -0.213, 1-sigma level 0.041 Q1 1 0.0617 0.5742 0.2622 11.00000 0.05 0.31 Q2 1 0.0355 0.6192 0.3379 11.00000 0.05 0.30 Q3 1 0.0856 0.4399 0.2565 11.00000 0.05 0.28 Q4 1 0.0386 0.7071 0.2601 11.00000 0.05 0.27 Q5 1 0.1801 0.6820 0.3656 11.00000 0.05 0.26 Q6 1 0.2205 0.5249 0.2232 11.00000 0.05 0.24 Q7 1 -0.1183 0.8560 0.1339 11.00000 0.05 0.24 Q8 1 0.3470 0.7608 0.3808 11.00000 0.05 0.23 Q9 1 0.4367 0.3634 0.1823 11.00000 0.05 0.22 Q10 1 0.4675 0.8568 0.3988 11.00000 0.05 0.22 ; _shelx_res_checksum 32135 _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MITIGEN holder' _olex2_submission_original_sample_id NDB_240625_SDc_C2S1 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.647 _oxdiff_exptl_absorpt_empirical_full_min 0.762 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 S1 S -0.15705(5) 0.78638(3) 0.09805(2) 0.01902(10) Uani 1 1 d . . . . . O1 O 0.48568(16) 0.18149(10) 0.15219(6) 0.0225(2) Uani 1 1 d . . . . . N1 N 0.06960(18) 0.78298(11) 0.23604(7) 0.0151(2) Uani 1 1 d . . . . . N2 N 0.23718(18) 0.83940(11) 0.27440(7) 0.0154(2) Uani 1 1 d . . . . . N3 N 0.16918(19) 0.97574(11) 0.10849(7) 0.0185(2) Uani 1 1 d . . . . . H3A H 0.266937 1.006554 0.138516 0.022 Uiso 1 1 calc R U . . . H3B H 0.157451 1.026087 0.051927 0.022 Uiso 1 1 calc R U . . . C1 C 0.0392(2) 0.85316(13) 0.14855(8) 0.0151(2) Uani 1 1 d . . . . . C2 C 0.2478(2) 0.75165(13) 0.35469(8) 0.0149(2) Uani 1 1 d . . . . . C3 C 0.4138(2) 0.78377(13) 0.41096(8) 0.0158(2) Uani 1 1 d . . . . . C4 C 0.5824(2) 0.89886(14) 0.37347(8) 0.0186(3) Uani 1 1 d . . . . . H4 H 0.589590 0.955323 0.311690 0.022 Uiso 1 1 calc R U . . . C5 C 0.7384(2) 0.93005(14) 0.42663(9) 0.0216(3) Uani 1 1 d . . . . . H5 H 0.852448 1.007895 0.401023 0.026 Uiso 1 1 calc R U . . . C6 C 0.7293(2) 0.84819(15) 0.51724(9) 0.0214(3) Uani 1 1 d . . . . . H6 H 0.836599 0.870361 0.553287 0.026 Uiso 1 1 calc R U . . . C7 C 0.5635(2) 0.73416(14) 0.55491(8) 0.0199(3) Uani 1 1 d . . . . . H7 H 0.556795 0.678439 0.616810 0.024 Uiso 1 1 calc R U . . . C8 C 0.4068(2) 0.70147(13) 0.50190(8) 0.0178(2) Uani 1 1 d . . . . . H8 H 0.294416 0.622732 0.527719 0.021 Uiso 1 1 calc R U . . . C9 C 0.0723(2) 0.62371(13) 0.38150(8) 0.0155(2) Uani 1 1 d . . . . . H9A H -0.066138 0.640767 0.423608 0.019 Uiso 1 1 calc R U . . . H9B H 0.149727 0.526966 0.409580 0.019 Uiso 1 1 calc R U . . . C10 C -0.0034(2) 0.62851(13) 0.28917(7) 0.0145(2) Uani 1 1 d . . . . . H10 H -0.180559 0.616729 0.294175 0.017 Uiso 1 1 calc R U . . . C11 C 0.1285(2) 0.51253(13) 0.24990(7) 0.0145(2) Uani 1 1 d . . . . . C12 C 0.3520(2) 0.54257(13) 0.19900(8) 0.0175(2) Uani 1 1 d . . . . . H12 H 0.420911 0.638505 0.187148 0.021 Uiso 1 1 calc R U . . . C13 C 0.4775(2) 0.43542(14) 0.16496(8) 0.0186(2) Uani 1 1 d . . . . . H13 H 0.629593 0.458351 0.129810 0.022 Uiso 1 1 calc R U . . . C14 C 0.3781(2) 0.29451(13) 0.18288(8) 0.0173(2) Uani 1 1 d . . . . . C15 C 0.1557(2) 0.26159(14) 0.23536(8) 0.0192(3) Uani 1 1 d . . . . . H15 H 0.088915 0.164717 0.248740 0.023 Uiso 1 1 calc R U . . . C16 C 0.0324(2) 0.37008(14) 0.26795(8) 0.0173(2) Uani 1 1 d . . . . . H16 H -0.119767 0.347197 0.303080 0.021 Uiso 1 1 calc R U . . . C17 C 0.6774(2) 0.22183(15) 0.07925(9) 0.0255(3) Uani 1 1 d . . . . . H17A H 0.625582 0.304623 0.030172 0.038 Uiso 1 1 calc R U . . . H17B H 0.721542 0.135237 0.057179 0.038 Uiso 1 1 calc R U . . . H17C H 0.816093 0.253187 0.100580 0.038 Uiso 1 1 calc R U . . . 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 0.02069(17) 0.02018(16) 0.01488(16) -0.00076(11) -0.00548(11) -0.00677(11) O1 0.0252(5) 0.0178(4) 0.0258(5) -0.0109(4) 0.0036(4) -0.0027(3) N1 0.0193(5) 0.0128(5) 0.0134(5) -0.0029(4) -0.0042(4) -0.0026(4) N2 0.0177(5) 0.0150(5) 0.0149(5) -0.0055(4) -0.0036(4) -0.0006(4) N3 0.0236(5) 0.0168(5) 0.0143(5) -0.0012(4) -0.0059(4) -0.0050(4) C1 0.0168(6) 0.0143(5) 0.0140(5) -0.0042(4) -0.0017(4) 0.0013(4) C2 0.0173(6) 0.0139(5) 0.0139(5) -0.0050(4) -0.0013(4) 0.0012(4) C3 0.0183(6) 0.0150(5) 0.0156(6) -0.0067(4) -0.0038(4) 0.0030(4) C4 0.0206(6) 0.0172(6) 0.0182(6) -0.0053(5) -0.0031(5) 0.0006(5) C5 0.0211(6) 0.0202(6) 0.0251(6) -0.0083(5) -0.0043(5) -0.0021(5) C6 0.0207(6) 0.0248(6) 0.0236(6) -0.0127(5) -0.0082(5) 0.0031(5) C7 0.0219(6) 0.0231(6) 0.0161(6) -0.0074(5) -0.0049(5) 0.0053(5) C8 0.0197(6) 0.0173(6) 0.0164(6) -0.0053(5) -0.0020(4) 0.0007(4) C9 0.0194(6) 0.0144(5) 0.0119(5) -0.0030(4) -0.0016(4) -0.0006(4) C10 0.0166(6) 0.0134(5) 0.0124(5) -0.0015(4) -0.0020(4) -0.0018(4) C11 0.0173(6) 0.0152(5) 0.0113(5) -0.0035(4) -0.0040(4) -0.0007(4) C12 0.0181(6) 0.0147(5) 0.0196(6) -0.0046(5) -0.0016(5) -0.0037(4) C13 0.0170(6) 0.0191(6) 0.0193(6) -0.0058(5) 0.0003(4) -0.0029(5) C14 0.0213(6) 0.0166(6) 0.0155(5) -0.0069(4) -0.0031(4) 0.0010(5) C15 0.0244(6) 0.0157(6) 0.0178(6) -0.0055(5) -0.0011(5) -0.0064(5) C16 0.0186(6) 0.0189(6) 0.0141(5) -0.0049(4) 0.0005(4) -0.0053(5) C17 0.0242(7) 0.0251(7) 0.0277(7) -0.0123(5) 0.0050(5) 0.0012(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0960 0 0 -1 0.1289 -1 -3 -2 0.2518 2 3 1 0.3459 0 1 1 0.3028 -2 3 6 0.2506 -1 3 4 0.2533 -3 2 5 0.2598 3 -1 -4 0.2778 2 -1 4 0.1819 1 -1 4 0.1401 1 0 5 0.1527 0 -1 -1 0.3312 -1 2 -2 0.1563 -1 4 -1 0.2067 -1 1 -4 0.1102 0 1 -1 0.1762 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 C14 O1 C17 117.36(10) . . ? N2 N1 C10 112.29(9) . . ? C1 N1 N2 118.58(9) . . ? C1 N1 C10 126.78(10) . . ? C2 N2 N1 108.39(9) . . ? H3A N3 H3B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? N1 C1 S1 120.40(9) . . ? N3 C1 S1 123.88(9) . . ? N3 C1 N1 115.71(10) . . ? N2 C2 C3 120.13(11) . . ? N2 C2 C9 113.17(10) . . ? C3 C2 C9 126.68(10) . . ? C4 C3 C2 119.87(11) . . ? C8 C3 C2 120.97(11) . . ? C8 C3 C4 119.16(11) . . ? C3 C4 H4 120.0 . . ? C5 C4 C3 119.99(11) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.49(12) . . ? C6 C5 H5 119.8 . . ? C5 C6 H6 120.0 . . ? C7 C6 C5 119.98(11) . . ? C7 C6 H6 120.0 . . ? C6 C7 H7 120.0 . . ? C6 C7 C8 119.95(11) . . ? C8 C7 H7 120.0 . . ? C3 C8 H8 119.8 . . ? C7 C8 C3 120.44(11) . . ? C7 C8 H8 119.8 . . ? C2 C9 H9A 111.4 . . ? C2 C9 H9B 111.4 . . ? C2 C9 C10 101.75(9) . . ? H9A C9 H9B 109.3 . . ? C10 C9 H9A 111.4 . . ? C10 C9 H9B 111.4 . . ? N1 C10 C9 99.96(9) . . ? N1 C10 H10 110.8 . . ? N1 C10 C11 111.75(9) . . ? C9 C10 H10 110.8 . . ? C11 C10 C9 112.29(9) . . ? C11 C10 H10 110.8 . . ? C12 C11 C10 121.11(10) . . ? C12 C11 C16 118.35(11) . . ? C16 C11 C10 120.47(10) . . ? C11 C12 H12 119.2 . . ? C11 C12 C13 121.52(11) . . ? C13 C12 H12 119.2 . . ? C12 C13 H13 120.3 . . ? C14 C13 C12 119.38(11) . . ? C14 C13 H13 120.3 . . ? O1 C14 C13 124.07(11) . . ? O1 C14 C15 116.12(11) . . ? C13 C14 C15 119.81(11) . . ? C14 C15 H15 120.0 . . ? C16 C15 C14 120.02(11) . . ? C16 C15 H15 120.0 . . ? C11 C16 H16 119.5 . . ? C15 C16 C11 120.90(11) . . ? C15 C16 H16 119.5 . . ? O1 C17 H17A 109.5 . . ? O1 C17 H17B 109.5 . . ? O1 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 1.6847(12) . ? O1 C14 1.3701(14) . ? O1 C17 1.4348(16) . ? N1 N2 1.3865(14) . ? N1 C1 1.3613(15) . ? N1 C10 1.4802(14) . ? N2 C2 1.2874(15) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N3 C1 1.3292(15) . ? C2 C3 1.4669(16) . ? C2 C9 1.5108(16) . ? C3 C4 1.4043(17) . ? C3 C8 1.3980(16) . ? C4 H4 0.9500 . ? C4 C5 1.3858(17) . ? C5 H5 0.9500 . ? C5 C6 1.3915(18) . ? C6 H6 0.9500 . ? C6 C7 1.3876(19) . ? C7 H7 0.9500 . ? C7 C8 1.3928(17) . ? C8 H8 0.9500 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.5499(15) . ? C10 H10 1.0000 . ? C10 C11 1.5176(16) . ? C11 C12 1.3885(17) . ? C11 C16 1.3953(16) . ? C12 H12 0.9500 . ? C12 C13 1.3915(17) . ? C13 H13 0.9500 . ? C13 C14 1.3899(17) . ? C14 C15 1.3951(17) . ? C15 H15 0.9500 . ? C15 C16 1.3848(17) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C14 C15 C16 -178.91(11) . . . . ? N1 N2 C2 C3 179.37(10) . . . . ? N1 N2 C2 C9 -2.41(13) . . . . ? N1 C10 C11 C12 25.91(15) . . . . ? N1 C10 C11 C16 -157.24(10) . . . . ? N2 N1 C1 S1 178.43(8) . . . . ? N2 N1 C1 N3 -2.77(16) . . . . ? N2 N1 C10 C9 20.10(12) . . . . ? N2 N1 C10 C11 -98.89(11) . . . . ? N2 C2 C3 C4 -8.15(17) . . . . ? N2 C2 C3 C8 171.74(11) . . . . ? N2 C2 C9 C10 14.63(13) . . . . ? C1 N1 N2 C2 -175.95(10) . . . . ? C1 N1 C10 C9 -177.70(11) . . . . ? C1 N1 C10 C11 63.30(15) . . . . ? C2 C3 C4 C5 179.60(11) . . . . ? C2 C3 C8 C7 -179.26(11) . . . . ? C2 C9 C10 N1 -19.12(11) . . . . ? C2 C9 C10 C11 99.47(10) . . . . ? C3 C2 C9 C10 -167.29(11) . . . . ? C3 C4 C5 C6 -0.09(19) . . . . ? C4 C3 C8 C7 0.64(17) . . . . ? C4 C5 C6 C7 0.14(19) . . . . ? C5 C6 C7 C8 0.20(19) . . . . ? C6 C7 C8 C3 -0.59(18) . . . . ? C8 C3 C4 C5 -0.30(18) . . . . ? C9 C2 C3 C4 173.89(11) . . . . ? C9 C2 C3 C8 -6.22(18) . . . . ? C9 C10 C11 C12 -85.49(13) . . . . ? C9 C10 C11 C16 91.36(13) . . . . ? C10 N1 N2 C2 -12.14(13) . . . . ? C10 N1 C1 S1 17.23(16) . . . . ? C10 N1 C1 N3 -163.98(11) . . . . ? C10 C11 C12 C13 178.07(11) . . . . ? C10 C11 C16 C15 -177.45(11) . . . . ? C11 C12 C13 C14 -0.58(18) . . . . ? C12 C11 C16 C15 -0.52(17) . . . . ? C12 C13 C14 O1 179.56(11) . . . . ? C12 C13 C14 C15 -0.65(18) . . . . ? C13 C14 C15 C16 1.28(18) . . . . ? C14 C15 C16 C11 -0.69(18) . . . . ? C16 C11 C12 C13 1.16(18) . . . . ? C17 O1 C14 C13 -16.96(17) . . . . ? C17 O1 C14 C15 163.24(11) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0007 -0.0010 1.0002 0.0113 -0.0995 -0.0285 0.0007 0.0010 -1.0002 -0.0113 0.0995 0.0285 -0.9985 -3.0003 -2.0006 0.2115 -0.1006 0.5027 1.9986 2.9883 1.0019 -0.4977 0.2100 -0.4890 -0.0011 0.9994 0.9987 0.0250 -0.0033 -0.1714 -2.0124 2.9976 6.0225 0.6609 -0.3335 -0.5675 -0.9975 3.0112 4.0220 0.3599 -0.1219 -0.5290 -3.0043 2.0186 5.0247 0.9092 -0.3396 -0.3825 3.0058 -1.0168 -4.0186 -0.8849 0.3358 0.2105 2.0025 -1.0161 4.0000 -0.5202 -0.4721 -0.0024 1.0019 -1.0091 4.0024 -0.2450 -0.4831 0.0131 1.0001 -0.0085 5.0043 -0.2197 -0.4866 -0.1586 0.0004 -0.9996 -1.0006 -0.0248 0.0035 0.1715 -1.0003 1.9929 -1.9955 0.2801 0.3781 -0.2112 -0.9958 3.9853 -0.9958 0.3171 0.4701 -0.5247 -0.9935 0.9876 -3.9980 0.2424 0.4806 -0.0103 0.0004 1.0001 -0.9996 0.0025 0.1953 -0.1144