#------------------------------------------------------------------------------ #$Date: 2026-05-01 01:26:31 +0100 (Fri, 01 May 2026) $ #$Revision: 305679 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064394.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_7064394 loop_ _publ_author_name 'Shepelenko, Konstantin' 'Gnatiuk, Irina' 'Kolotova, Uliana' 'Minyaev, Mikhail Evgenevich' 'Chernyshev, Victor' _publ_section_title ; Sustainable Ruthenium-Catalyzed C--H Alkylation of 2-(Hetero)aryl Benzimidazoles with Maleimides ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D6NJ00299D _journal_year 2026 _chemical_formula_moiety 'C22 H17 N3 O2 S' _chemical_formula_sum 'C22 H17 N3 O2 S' _chemical_formula_weight 387.44 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2025-05-22 _audit_creation_method ; Olex2 1.5-ac6-020 (compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966) ; _audit_update_record ; 2025-10-12 deposited with the CCDC. 2026-04-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.1472(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.77135(6) _cell_length_b 14.83370(7) _cell_length_c 9.99137(5) _cell_measurement_reflns_used 26298 _cell_measurement_temperature 100.0(3) _cell_measurement_theta_max 79.5220 _cell_measurement_theta_min 4.6170 _cell_volume 1843.216(16) _computing_cell_refinement 'CrysAlisPro 1.171.44.111a (Rigaku OD, 2025)' _computing_data_collection 'CrysAlisPro system (CCD 44.106a 64-bit (release 18-04-2025))' _computing_data_reduction 'CrysAlisPro 1.171.44.111a (Rigaku OD, 2025)' _computing_molecular_graphics 'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, Acta Cryst., 2015, A71, 3-8)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(3) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _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 55.00 122.00 0.50 0.10 -- 46.59-165.00 82.00 134 2 \w 43.00 111.00 0.50 0.30 -- 113.25-125.00 90.00 136 3 \w 55.00 139.00 0.50 0.30 -- 113.25-165.00 82.00 168 4 \w 59.00 85.00 0.50 0.30 -- 113.25-125.00 30.00 52 5 \w 44.00 77.00 0.50 0.30 -- 113.25-125.00 -30.00 66 6 \w 84.00 111.00 0.50 0.30 -- 113.25-125.00 -30.00 54 7 \w 41.00 106.00 0.50 0.30 -- 113.25 -95.00 -90.00 130 8 \w 44.00 109.00 0.50 0.30 -- 113.25-116.00-129.00 130 9 \w 42.00 107.00 0.50 0.30 -- 113.25-103.00-134.89 130 10 \w 41.00 106.00 0.50 0.30 -- 113.25 -95.00-120.00 130 11 \w 41.00 106.00 0.50 0.30 -- 113.25 -95.00 -90.00 130 12 \w 28.00 88.00 0.50 0.10 -- 46.59-116.00-129.00 120 13 \w 46.00 82.00 0.50 0.30 -- 113.25 -95.00 150.00 72 14 \w 41.00 86.00 0.50 0.30 -- 113.25 -95.00 -30.00 90 15 \w 109.00 135.00 0.50 0.30 -- 113.25 -87.00-107.50 52 16 \w 69.00 102.00 0.50 0.30 -- 113.25 -77.00 -30.00 66 17 \w 45.00 70.00 0.50 0.30 -- 113.25 -61.00 -60.00 50 18 \w 48.00 101.00 0.50 0.30 -- 113.25 -77.00 -90.00 106 19 \w 54.00 97.00 0.50 0.30 -- 113.25 -77.00-150.00 86 20 \w 48.00 73.00 0.50 0.30 -- 113.25 -77.00-120.00 50 21 \w -29.00 27.00 0.50 0.10 -- 46.59 -19.00-150.00 112 22 \w -29.00 27.00 0.50 0.10 -- 46.59 -19.00 120.00 112 23 \w 41.00 71.00 0.50 0.30 -- 113.25 -61.00 90.00 60 24 \w 41.00 71.00 0.50 0.30 -- 113.25 -61.00 -90.00 60 25 \w 100.00 126.00 0.50 0.30 -- 113.25 15.00 -90.00 52 26 \w 100.00 131.00 0.50 0.30 -- 113.25 61.00-150.00 62 27 \w 138.00 177.00 0.50 0.30 -- 113.25 61.00-150.00 78 28 \w 95.00 142.00 0.50 0.30 -- 113.25 77.00 -90.00 94 29 \w 99.00 174.00 0.50 0.30 -- 113.25 45.00 0.00 150 30 \w 147.00 178.00 0.50 0.30 -- 113.25 30.00 60.00 62 31 \w 99.00 178.00 0.50 0.30 -- 113.25 30.00 60.00 158 32 \w 105.00 131.00 0.50 0.30 -- 113.25 30.00 120.00 52 33 \w 146.00 178.00 0.50 0.30 -- 113.25 30.00 120.00 64 34 \w 138.00 178.00 0.50 0.30 -- 113.25 15.00 -90.00 80 35 \w 96.00 178.00 0.50 0.30 -- 113.25 15.00-120.00 164 36 \w 101.00 178.00 0.50 0.30 -- 113.25 116.00 -42.00 154 37 \w 69.00 119.00 0.50 0.10 -- 46.59 165.00 106.00 100 38 \w 69.00 155.00 0.50 0.30 -- 113.25 165.00 106.00 172 39 \w 95.00 178.00 0.50 0.30 -- 113.25 125.00 150.00 166 40 \w 95.00 178.00 0.50 0.30 -- 113.25 125.00 150.00 166 41 \w -27.00 29.00 0.50 0.10 -- -46.59 19.00 90.00 112 42 \w -83.00 -6.00 0.50 0.10 -- -46.59 116.00 -42.00 154 43 \w -83.00 -23.00 0.50 0.30 -- -91.75 116.00 -42.00 120 44 \w -113.00 -33.00 0.50 0.30 -- -91.75 165.00 106.00 160 45 \w -27.00 29.00 0.50 0.10 -- -46.59 19.00 120.00 112 46 \w -118.00 -47.00 0.50 0.10 -- -46.59-165.00 82.00 142 47 \w -161.00 -79.00 0.50 0.30 -- -91.75-116.00-129.00 164 48 \w 94.00 120.00 0.50 0.30 -- 113.25 12.00-171.00 52 49 \w 24.00 108.00 0.50 0.10 -- 46.46 77.00 -30.00 168 50 \w 92.00 118.00 0.50 0.10 -- 46.46 77.00 -60.00 52 51 \w 30.00 57.00 0.50 0.10 -- 46.46 57.00 -90.00 54 52 \w 39.00 67.00 0.50 0.10 -- 46.46 19.00 -90.00 56 53 \w 23.00 55.00 0.50 0.10 -- 46.46 77.00 -90.00 64 54 \w 25.00 52.00 0.50 0.10 -- 46.46 77.00-150.00 54 55 \w 30.00 60.00 0.50 0.10 -- 46.46 57.00-150.00 60 56 \w 24.00 56.00 0.50 0.10 -- 46.46 77.00 -60.00 64 57 \w 34.00 80.00 0.50 0.10 -- 46.46 38.00-150.00 92 58 \w -98.00 -72.00 0.50 0.30 -- -91.75 -66.00 -85.90 52 59 \w -94.00 -68.00 0.50 0.30 -- -91.75 -76.00-112.64 52 60 \w -93.00 -68.00 0.50 0.30 -- -91.75 -77.00 -60.00 50 61 \w -98.00 -72.00 0.50 0.30 -- -91.75 -66.00 -62.24 52 62 \w -100.00 -74.00 0.50 0.30 -- -91.75 -71.00 -84.27 52 63 \w -96.00 -70.00 0.50 0.30 -- -91.75 -74.00-169.48 52 64 \w -98.00 -72.00 0.50 0.30 -- -91.75 -72.00 -47.54 52 65 \w -100.00 -74.00 0.50 0.30 -- -91.75 -61.00 -60.00 52 66 \w -94.00 -68.00 0.50 0.30 -- -91.75 -77.00-101.29 52 67 \w -99.00 -73.00 0.50 0.30 -- -91.75 -65.00-177.37 52 68 \w -95.00 -69.00 0.50 0.30 -- -91.75 -77.00-150.00 52 69 \w -96.00 -70.00 0.50 0.30 -- -91.75 -77.00 0.00 52 70 \w -96.00 -70.00 0.50 0.30 -- -91.75 -74.00 -22.82 52 71 \w -152.00-126.00 0.50 0.30 -- -91.75 -77.00 -60.00 52 72 \w -136.00-110.00 0.50 0.30 -- -91.75 -77.00 -9.67 52 73 \w -94.00 -68.00 0.50 0.30 -- -91.75 -77.00 -30.00 52 74 \w -94.00 -68.00 0.50 0.30 -- -91.75 -77.00 -90.00 52 75 \w -94.00 -68.00 0.50 0.30 -- -91.75 -77.00-140.90 52 76 \w -98.00 -72.00 0.50 0.30 -- -91.75 -66.00 -6.91 52 77 \w -98.00 -72.00 0.50 0.30 -- -91.75 -66.00-151.41 52 78 \w -97.00 -71.00 0.50 0.30 -- -91.75 -74.00-149.62 52 79 \w -98.00 -73.00 0.50 0.30 -- -91.75 -64.00 -91.82 50 80 \w -94.00 -68.00 0.50 0.30 -- -91.75 -77.00-120.00 52 81 \w -94.00 -69.00 0.50 0.30 -- -91.75 -74.00-133.43 50 82 \w -99.00 -73.00 0.50 0.30 -- -91.75 -64.00 -56.83 52 83 \w -103.00 -77.00 0.50 0.30 -- -91.75 -51.00 -70.50 52 84 \w -101.00 -76.00 0.50 0.30 -- -91.75 -51.00-118.76 50 85 \w -93.00 -68.00 0.50 0.30 -- -91.75 -77.00 -9.67 50 86 \w -95.00 -69.00 0.50 0.30 -- -91.75 -74.00-176.23 52 87 \w -101.00 -76.00 0.50 0.30 -- -91.75 -56.00 -9.89 50 88 \w -95.00 -69.00 0.50 0.30 -- -91.75 -73.00-113.22 52 89 \w 45.00 71.00 0.50 0.30 -- 113.25 -95.00 0.00 52 90 \w 99.00 125.00 0.50 0.30 -- 113.25 -83.00-103.34 52 91 \w 91.00 119.00 0.50 0.30 -- 113.25 77.00-150.00 56 92 \w 90.00 119.00 0.50 0.30 -- 113.25 77.00 0.00 58 93 \w 148.00 176.00 0.50 0.30 -- 113.25 77.00 -90.00 56 94 \w 90.00 116.00 0.50 0.30 -- 113.25 77.00 -90.00 52 95 \w 98.00 124.00 0.50 0.30 -- 113.25 61.00-120.00 52 96 \w 139.00 172.00 0.50 0.30 -- 113.25 61.00 60.00 66 97 \w 147.00 173.00 0.50 0.30 -- 113.25 61.00 90.00 52 98 \w 103.00 129.00 0.50 0.30 -- 113.25 61.00 90.00 52 99 \w 106.00 132.00 0.50 0.30 -- 113.25 61.00 60.00 52 100 \w 41.00 82.00 0.50 0.30 -- 113.25 -77.00-180.00 82 101 \w 149.00 178.00 0.50 0.30 -- 113.25 61.00 150.00 58 102 \w 98.00 131.00 0.50 0.30 -- 113.25 125.00 60.00 66 103 \w 41.00 66.00 0.50 0.30 -- 113.25 -61.00 -30.00 50 104 \w 129.00 155.00 0.50 0.30 -- 113.25 77.00 -60.00 52 105 \w 147.00 173.00 0.50 0.30 -- 113.25 45.00 90.00 52 106 \w 102.00 128.00 0.50 0.30 -- 113.25 45.00 90.00 52 107 \w 96.00 125.00 0.50 0.30 -- 113.25 61.00 -30.00 58 108 \w 50.00 76.00 0.50 0.30 -- 113.25 -77.00 -30.00 52 109 \w 139.00 173.00 0.50 0.30 -- 113.25 77.00-180.00 68 110 \w 63.00 92.00 0.50 0.30 -- 113.25 -95.00 90.00 58 111 \w 90.00 116.00 0.50 0.30 -- 113.25 77.00 -60.00 52 112 \w 60.00 86.00 0.50 0.30 -- 113.25-125.00 -90.00 52 113 \w 97.00 123.00 0.50 0.30 -- 113.25 77.00-180.00 52 114 \w 90.00 116.00 0.50 0.30 -- 113.25 77.00 -30.00 52 115 \w 152.00 178.00 0.50 0.30 -- 113.25 77.00-120.00 52 116 \w 139.00 177.00 0.50 0.30 -- 113.25 61.00 30.00 76 117 \w 135.00 161.00 0.50 0.30 -- 113.25 61.00 -90.00 52 118 \w 151.00 177.00 0.50 0.30 -- 113.25 15.00 0.00 52 119 \w 96.00 122.00 0.50 0.30 -- 113.25 61.00-150.00 52 120 \w 121.00 147.00 0.50 0.30 -- 113.25 30.00 0.00 52 121 \w 112.00 137.00 0.50 0.30 -- 113.25 30.00 -30.00 50 122 \w 97.00 125.00 0.50 0.30 -- 113.25 61.00 -90.00 56 123 \w 146.00 172.00 0.50 0.30 -- 113.25 125.00-180.00 52 124 \w 121.00 147.00 0.50 0.30 -- 113.25 125.00 -90.00 52 125 \w 90.00 134.00 0.50 0.30 -- 113.25 77.00-120.00 88 126 \w 129.00 155.00 0.50 0.30 -- 113.25 30.00-120.00 52 127 \w 120.00 146.00 0.50 0.30 -- 113.25 30.00-180.00 52 128 \w 145.00 171.00 0.50 0.30 -- 113.25 77.00 120.00 52 129 \w 105.00 155.00 0.50 0.30 -- 113.25 45.00 30.00 100 130 \w 100.00 136.00 0.50 0.30 -- 113.25 45.00 -30.00 72 131 \w 96.00 122.00 0.50 0.30 -- 113.25 77.00 120.00 52 132 \w 107.00 133.00 0.50 0.30 -- 113.25 45.00-150.00 52 133 \w 48.00 74.00 0.50 0.30 -- 113.25-125.00 30.00 52 134 \w 81.00 107.00 0.50 0.30 -- 113.25-125.00 -60.00 52 135 \w 45.00 73.00 0.50 0.30 -- 113.25-125.00-150.00 56 136 \w 100.00 136.00 0.50 0.30 -- 113.25 61.00 -60.00 72 ; _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 -0.1211309000 _diffrn_orient_matrix_UB_12 -0.0073170000 _diffrn_orient_matrix_UB_13 -0.0049422000 _diffrn_orient_matrix_UB_21 -0.0047124000 _diffrn_orient_matrix_UB_22 0.1023649000 _diffrn_orient_matrix_UB_23 0.0239068000 _diffrn_orient_matrix_UB_31 -0.0254453000 _diffrn_orient_matrix_UB_32 0.0159139000 _diffrn_orient_matrix_UB_33 -0.1564738000 _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 0.0322 _diffrn_reflns_av_unetI/netI 0.0192 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 30432 _diffrn_reflns_point_group_measured_fraction_full 0.976 _diffrn_reflns_point_group_measured_fraction_max 0.957 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.848 _diffrn_reflns_theta_min 4.640 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.755 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.386 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.44.111a (Rigaku Oxford Diffraction, 2025) 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 colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_description pyramid _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.616 _exptl_crystal_size_mid 0.254 _exptl_crystal_size_min 0.166 _refine_diff_density_max 0.207 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.033 _refine_ls_abs_structure_details ; Flack x determined using 1823 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.001(6) _refine_ls_extinction_coef 0.00233(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL 2018/3 (Sheldrick, Acta Cryst., 2015, C71, 3-8)' _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 269 _refine_ls_number_reflns 3862 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0233 _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^)+(0.0373P)^2^+0.6919P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.0606 _reflns_Friedel_coverage 0.915 _reflns_Friedel_fraction_full 0.952 _reflns_Friedel_fraction_max 0.917 _reflns_number_gt 3855 _reflns_number_total 3862 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00299d2.cif _cod_data_source_block RuSk-15-32 _cod_original_cell_volume 1843.215(16) _cod_database_code 7064394 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C22 H17 N3 O2 S' _chemical_oxdiff_usercomment RuSk-15-32 _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 0.759 _shelx_estimated_absorpt_t_min 0.411 _diffrn_oxdiff_digest_od_ed ; ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates and stretchable bonds: C3(H3) 2.b Secondary CH2 refined with riding coordinates and stretchable bonds: C2(H2A,H2B) 2.c Aromatic/amide H refined with riding coordinates and stretchable bonds: C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20) 2.d Idealised Me refined as rotating group with stretchable bonds: C22(H22A,H22B,H22C) ; _shelx_res_file ; TITL RuSk-15-32 in Cc rusk-15-32.res created by SHELXL-2018/3 at 09:08:25 on 22-May-2025 REM SHELXT solution in Cc REM R1 0.057, Rweak 0.036, Alpha 0.001, Orientation as input REM Flack x = 0.016 ( 0.006 ) from Parsons' quotients REM Formula found by SHELXT: C22 N3 O2 S CELL 1.54184 12.77135 14.8337 9.99137 90 103.1472 90 ZERR 4 0.00006 0.00007 0.00005 0 0.0004 0 LATT -7 SYMM +X,-Y,0.5+Z SFAC C H N O S UNIT 88 68 12 8 4 L.S. 7 PLAN 17 SIZE 0.166 0.254 0.616 TEMP -173.15 CONF list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.037300 0.691900 EXTI 0.002330 FVAR 0.58980 S1 5 0.826909 0.492202 0.508409 11.00000 0.01796 0.02058 = 0.02266 -0.00050 0.00630 0.00474 N1 3 0.405721 0.574876 0.589253 11.00000 0.01592 0.01530 = 0.01382 0.00138 0.00344 0.00001 C1 1 0.460212 0.637716 0.685499 11.00000 0.01943 0.01731 = 0.01397 0.00106 0.00587 -0.00009 C2 1 0.566956 0.598129 0.758095 11.00000 0.01864 0.01659 = 0.01391 -0.00025 0.00260 0.00089 AFIX 24 H2A 2 0.570107 0.591222 0.852007 11.00000 -1.20000 H2B 2 0.623605 0.635364 0.747352 11.00000 -1.20000 AFIX 0 C3 1 0.573475 0.506341 0.690193 11.00000 0.01770 0.01570 = 0.01390 0.00316 0.00252 0.00059 AFIX 14 H3 2 0.571207 0.461274 0.757468 11.00000 -1.20000 AFIX 0 C4 1 0.468910 0.499426 0.580410 11.00000 0.01689 0.01464 = 0.01724 0.00322 0.00577 -0.00124 O1 4 0.424882 0.710953 0.704759 11.00000 0.02359 0.01770 = 0.02299 -0.00309 0.00326 0.00544 O2 4 0.442895 0.437418 0.501427 11.00000 0.01976 0.01696 = 0.02646 -0.00513 0.00314 -0.00072 C5 1 0.313997 0.599245 0.482986 11.00000 0.01571 0.01469 = 0.01663 0.00307 0.00198 -0.00149 C6 1 0.225933 0.640489 0.516315 11.00000 0.01989 0.02443 = 0.02375 0.00098 0.00556 0.00105 AFIX 44 H6 2 0.223144 0.648878 0.609419 11.00000 -1.20000 AFIX 0 C7 1 0.141460 0.669459 0.410586 11.00000 0.01948 0.02422 = 0.03843 0.00225 0.00302 0.00413 AFIX 44 H7 2 0.080899 0.698577 0.432531 11.00000 -1.20000 AFIX 0 C8 1 0.144325 0.656535 0.274385 11.00000 0.02303 0.02170 = 0.03187 0.00717 -0.00519 -0.00144 AFIX 44 H8 2 0.085123 0.677173 0.201568 11.00000 -1.20000 AFIX 0 C9 1 0.232363 0.613856 0.242212 11.00000 0.02833 0.02463 = 0.01903 0.00440 0.00075 -0.00516 AFIX 44 H9 2 0.234111 0.603380 0.145310 11.00000 -1.20000 AFIX 0 C10 1 0.317821 0.585963 0.346278 11.00000 0.01996 0.02280 = 0.01785 0.00224 0.00426 -0.00230 AFIX 44 H10 2 0.381209 0.556750 0.323351 11.00000 -1.20000 AFIX 0 C11 1 0.718587 0.544067 0.554020 11.00000 0.01475 0.01563 = 0.01478 -0.00136 0.00194 0.00179 C12 1 0.670468 0.486850 0.631601 11.00000 0.01654 0.01449 = 0.01376 -0.00071 0.00008 0.00134 C13 1 0.723007 0.401830 0.651967 11.00000 0.02369 0.01627 = 0.01676 0.00213 0.00055 0.00468 AFIX 44 H13 2 0.699707 0.352203 0.704997 11.00000 -1.20000 AFIX 0 C14 1 0.808195 0.394823 0.592002 11.00000 0.02575 0.01936 = 0.02230 0.00018 0.00274 0.00825 AFIX 44 H14 2 0.852136 0.342112 0.596022 11.00000 -1.20000 AFIX 0 C15 1 0.678759 0.631590 0.497820 11.00000 0.01637 0.01427 = 0.01329 -0.00174 0.00344 -0.00106 N2 3 0.740567 0.702974 0.472016 11.00000 0.01611 0.01672 = 0.01435 0.00023 0.00263 -0.00172 N3 3 0.574600 0.649198 0.464752 11.00000 0.01640 0.01418 = 0.01670 0.00134 0.00443 0.00090 C16 1 0.669665 0.770835 0.417852 11.00000 0.02060 0.01502 = 0.01193 -0.00055 0.00290 0.00027 C17 1 0.686933 0.858367 0.375021 11.00000 0.02624 0.01716 = 0.01621 0.00043 0.00554 -0.00482 AFIX 44 H17 2 0.757838 0.880756 0.376375 11.00000 -1.20000 AFIX 0 C18 1 0.596001 0.910791 0.330622 11.00000 0.03497 0.01238 = 0.01843 0.00120 0.00693 -0.00114 AFIX 44 H18 2 0.603926 0.971018 0.300608 11.00000 -1.20000 AFIX 0 C19 1 0.492143 0.877970 0.328384 11.00000 0.02915 0.01839 = 0.01621 0.00116 0.00574 0.00559 AFIX 44 H19 2 0.427793 0.918909 0.295244 11.00000 -1.20000 AFIX 0 C20 1 0.475729 0.791078 0.370372 11.00000 0.01974 0.01830 = 0.01777 0.00115 0.00619 0.00279 AFIX 44 H20 2 0.406528 0.769397 0.368470 11.00000 -1.20000 AFIX 0 C21 1 0.566759 0.737024 0.415742 11.00000 0.01982 0.01398 = 0.01243 -0.00031 0.00402 -0.00035 C22 1 0.857329 0.709931 0.491863 11.00000 0.01553 0.02614 = 0.02581 0.00514 0.00179 -0.00352 AFIX 138 H22A 2 0.879027 0.770729 0.512748 11.00000 -1.50000 H22B 2 0.877738 0.691758 0.409956 11.00000 -1.50000 H22C 2 0.891269 0.671839 0.565810 11.00000 -1.50000 AFIX 0 HKLF 4 REM RuSk-15-32 in Cc REM wR2 = 0.060602, GooF = S = 1.03691, Restrained GooF = 1.03662 for all data REM R1 = 0.023332 for 3855 Fo > 4sig(Fo) and 0.023379 for all 3862 data REM 269 parameters refined using 2 restraints END WGHT 0.0373 0.6919 REM Highest difference peak 0.207, deepest hole -0.147, 1-sigma level 0.033 Q1 1 0.6228 0.5012 0.6596 11.00000 0.05 0.21 Q2 1 0.6193 0.7646 0.4338 11.00000 0.05 0.18 Q3 1 0.7604 0.5210 0.5277 11.00000 0.05 0.17 Q4 1 0.5237 0.5013 0.6363 11.00000 0.05 0.17 Q5 1 0.6936 0.4424 0.6398 11.00000 0.05 0.16 Q6 1 0.7053 0.5275 0.6157 11.00000 0.05 0.16 Q7 1 0.5178 0.6222 0.7174 11.00000 0.05 0.15 Q8 1 0.6425 0.8780 0.3223 11.00000 0.05 0.15 Q9 1 0.8105 0.4379 0.5468 11.00000 0.05 0.15 Q10 1 0.7140 0.6596 0.4605 11.00000 0.05 0.15 Q11 1 0.6794 0.8040 0.3642 11.00000 0.05 0.14 Q12 1 0.3674 0.5943 0.5385 11.00000 0.05 0.14 Q13 1 0.4838 0.8376 0.3686 11.00000 0.05 0.14 Q14 1 0.7017 0.5781 0.4967 11.00000 0.05 0.14 Q15 1 0.5199 0.7704 0.4292 11.00000 0.05 0.13 Q16 1 0.7200 0.5831 0.5529 11.00000 0.05 0.13 Q17 1 0.5196 0.7587 0.3809 11.00000 0.05 0.12 ; _shelx_res_checksum 42372 _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 1.317 _oxdiff_exptl_absorpt_empirical_full_min 0.849 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, 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 0.82691(4) 0.49220(3) 0.50841(4) 0.02013(12) Uani 1 1 d . . . . . N1 N 0.40572(11) 0.57488(10) 0.58925(15) 0.0150(3) Uani 1 1 d . . . . . C1 C 0.46021(14) 0.63772(12) 0.68550(19) 0.0166(3) Uani 1 1 d . . . . . C2 C 0.56696(13) 0.59813(12) 0.75809(18) 0.0166(3) Uani 1 1 d . . . . . H2A H 0.57011(15) 0.59122(17) 0.8520(19) 0.020 Uiso 1 1 calc R U . . . H2B H 0.6236(11) 0.6354(7) 0.7474(3) 0.020 Uiso 1 1 calc R U . . . C3 C 0.57347(14) 0.50634(11) 0.69019(19) 0.0159(3) Uani 1 1 d . . . . . H3 H 0.57121(15) 0.4613(13) 0.7575(19) 0.019 Uiso 1 1 calc R U . . . C4 C 0.46891(15) 0.49943(11) 0.58041(19) 0.0160(3) Uani 1 1 d . . . . . O1 O 0.42488(11) 0.71095(9) 0.70476(14) 0.0218(3) Uani 1 1 d . . . . . O2 O 0.44289(10) 0.43742(9) 0.50143(15) 0.0214(3) Uani 1 1 d . . . . . C5 C 0.31400(13) 0.59924(11) 0.48299(19) 0.0160(3) Uani 1 1 d . . . . . C6 C 0.22593(15) 0.64049(13) 0.5163(2) 0.0226(4) Uani 1 1 d . . . . . H6 H 0.22314(17) 0.6489(3) 0.609(3) 0.027 Uiso 1 1 calc R U . . . C7 C 0.14146(16) 0.66946(14) 0.4106(2) 0.0279(4) Uani 1 1 d . . . . . H7 H 0.081(2) 0.6986(10) 0.4325(8) 0.034 Uiso 1 1 calc R U . . . C8 C 0.14433(16) 0.65653(13) 0.2744(2) 0.0274(4) Uani 1 1 d . . . . . H8 H 0.0851(18) 0.6772(6) 0.202(2) 0.033 Uiso 1 1 calc R U . . . C9 C 0.23236(16) 0.61386(14) 0.2422(2) 0.0247(4) Uani 1 1 d . . . . . H9 H 0.23411(17) 0.6034(4) 0.145(3) 0.030 Uiso 1 1 calc R U . . . C10 C 0.31782(14) 0.58596(13) 0.3463(2) 0.0202(4) Uani 1 1 d . . . . . H10 H 0.3812(17) 0.5568(8) 0.3234(6) 0.024 Uiso 1 1 calc R U . . . C11 C 0.71859(13) 0.54407(12) 0.55402(18) 0.0153(3) Uani 1 1 d . . . . . C12 C 0.67047(14) 0.48685(12) 0.63160(19) 0.0155(3) Uani 1 1 d . . . . . C13 C 0.72301(15) 0.40183(12) 0.6520(2) 0.0196(4) Uani 1 1 d . . . . . H13 H 0.6997(7) 0.3522(14) 0.7050(15) 0.023 Uiso 1 1 calc R U . . . C14 C 0.80819(16) 0.39482(13) 0.5920(2) 0.0229(4) Uani 1 1 d . . . . . H14 H 0.8521(13) 0.3421(16) 0.5960(2) 0.027 Uiso 1 1 calc R U . . . C15 C 0.67876(13) 0.63159(12) 0.49782(18) 0.0146(3) Uani 1 1 d . . . . . N2 N 0.74057(12) 0.70297(10) 0.47202(15) 0.0159(3) Uani 1 1 d . . . . . N3 N 0.57460(12) 0.64920(10) 0.46475(16) 0.0157(3) Uani 1 1 d . . . . . C16 C 0.66966(14) 0.77083(11) 0.41785(18) 0.0160(3) Uani 1 1 d . . . . . C17 C 0.68693(16) 0.85837(12) 0.3750(2) 0.0198(4) Uani 1 1 d . . . . . H17 H 0.7578(19) 0.8808(6) 0.3764(2) 0.024 Uiso 1 1 calc R U . . . C18 C 0.59600(17) 0.91079(12) 0.3306(2) 0.0218(4) Uani 1 1 d . . . . . H18 H 0.6039(3) 0.9710(19) 0.3006(9) 0.026 Uiso 1 1 calc R U . . . C19 C 0.49214(16) 0.87797(13) 0.3284(2) 0.0212(4) Uani 1 1 d . . . . . H19 H 0.4278(17) 0.9189(11) 0.2952(9) 0.025 Uiso 1 1 calc R U . . . C20 C 0.47573(14) 0.79108(12) 0.37037(19) 0.0183(4) Uani 1 1 d . . . . . H20 H 0.407(2) 0.7694(6) 0.3685(2) 0.022 Uiso 1 1 calc R U . . . C21 C 0.56676(14) 0.73702(11) 0.41574(18) 0.0154(3) Uani 1 1 d . . . . . C22 C 0.85733(14) 0.70993(14) 0.4919(2) 0.0230(4) Uani 1 1 d . . . . . H22A H 0.8790(4) 0.7707(11) 0.5127(18) 0.034 Uiso 1 1 calc R U . . . H22B H 0.8777(4) 0.6918(12) 0.4100(16) 0.034 Uiso 1 1 calc R U . . . H22C H 0.8913(6) 0.6718(11) 0.5658(18) 0.034 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 0.01796(19) 0.0206(2) 0.0227(2) -0.00050(17) 0.00630(15) 0.00474(16) N1 0.0159(6) 0.0153(6) 0.0138(7) 0.0014(5) 0.0034(5) 0.0000(5) C1 0.0194(8) 0.0173(8) 0.0140(8) 0.0011(6) 0.0059(6) -0.0001(6) C2 0.0186(8) 0.0166(8) 0.0139(9) -0.0002(6) 0.0026(6) 0.0009(6) C3 0.0177(8) 0.0157(8) 0.0139(9) 0.0032(6) 0.0025(7) 0.0006(6) C4 0.0169(8) 0.0146(8) 0.0172(9) 0.0032(6) 0.0058(7) -0.0012(6) O1 0.0236(6) 0.0177(6) 0.0230(7) -0.0031(5) 0.0033(5) 0.0054(5) O2 0.0198(6) 0.0170(6) 0.0265(7) -0.0051(5) 0.0031(5) -0.0007(5) C5 0.0157(8) 0.0147(7) 0.0166(9) 0.0031(6) 0.0020(6) -0.0015(6) C6 0.0199(9) 0.0244(9) 0.0238(10) 0.0010(7) 0.0056(7) 0.0011(7) C7 0.0195(9) 0.0242(10) 0.0384(12) 0.0022(8) 0.0030(8) 0.0041(7) C8 0.0230(9) 0.0217(9) 0.0319(11) 0.0072(8) -0.0052(8) -0.0014(7) C9 0.0283(9) 0.0246(9) 0.0190(10) 0.0044(7) 0.0008(8) -0.0052(7) C10 0.0200(8) 0.0228(9) 0.0179(10) 0.0022(7) 0.0043(7) -0.0023(7) C11 0.0147(7) 0.0156(7) 0.0148(8) -0.0014(6) 0.0019(6) 0.0018(6) C12 0.0165(8) 0.0145(8) 0.0138(9) -0.0007(6) 0.0001(6) 0.0013(6) C13 0.0237(9) 0.0163(8) 0.0168(9) 0.0021(6) 0.0005(7) 0.0047(7) C14 0.0258(9) 0.0194(9) 0.0223(10) 0.0002(7) 0.0027(7) 0.0083(7) C15 0.0164(7) 0.0143(8) 0.0133(8) -0.0017(6) 0.0034(6) -0.0011(6) N2 0.0161(7) 0.0167(7) 0.0144(7) 0.0002(5) 0.0026(5) -0.0017(5) N3 0.0164(7) 0.0142(7) 0.0167(7) 0.0013(5) 0.0044(5) 0.0009(5) C16 0.0206(8) 0.0150(8) 0.0119(8) -0.0006(6) 0.0029(6) 0.0003(6) C17 0.0262(9) 0.0172(8) 0.0162(9) 0.0004(6) 0.0055(7) -0.0048(7) C18 0.0350(10) 0.0124(8) 0.0184(9) 0.0012(6) 0.0069(7) -0.0011(7) C19 0.0291(9) 0.0184(8) 0.0162(9) 0.0012(7) 0.0057(7) 0.0056(7) C20 0.0197(8) 0.0183(8) 0.0178(9) 0.0011(6) 0.0062(7) 0.0028(6) C21 0.0198(8) 0.0140(8) 0.0124(8) -0.0003(6) 0.0040(6) -0.0004(6) C22 0.0155(8) 0.0261(9) 0.0258(10) 0.0051(7) 0.0018(7) -0.0035(7) 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 -1 1 0 0.0540 -1 -1 0 0.0384 0 0 1 0.2009 5 1 -1 0.0554 5 -5 -1 0.0972 0 1 0 0.1189 0 0 -1 0.4019 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 S1 C11 92.17(9) . . ? C1 N1 C5 122.18(14) . . ? C4 N1 C1 111.85(14) . . ? C4 N1 C5 122.78(15) . . ? N1 C1 C2 108.87(14) . . ? O1 C1 N1 124.11(17) . . ? O1 C1 C2 127.03(17) . . ? C1 C2 H2A 110.6 . . ? C1 C2 H2B 110.6 . . ? C1 C2 C3 105.49(14) . . ? H2A C2 H2B 108.8 . . ? C3 C2 H2A 110.6 . . ? C3 C2 H2B 110.6 . . ? C2 C3 H3 107.3 . . ? C4 C3 C2 104.55(13) . . ? C4 C3 H3 107.3 . . ? C12 C3 C2 118.22(14) . . ? C12 C3 H3 107.3 . . ? C12 C3 C4 111.62(15) . . ? N1 C4 C3 108.96(15) . . ? O2 C4 N1 125.12(17) . . ? O2 C4 C3 125.88(16) . . ? C6 C5 N1 120.22(17) . . ? C6 C5 C10 120.65(17) . . ? C10 C5 N1 119.00(16) . . ? C5 C6 H6 120.5 . . ? C5 C6 C7 119.0(2) . . ? C7 C6 H6 120.5 . . ? C6 C7 H7 119.6 . . ? C8 C7 C6 120.89(19) . . ? C8 C7 H7 119.6 . . ? C7 C8 H8 120.2 . . ? C7 C8 C9 119.63(19) . . ? C9 C8 H8 120.2 . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C5 C10 H10 120.1 . . ? C9 C10 C5 119.72(18) . . ? C9 C10 H10 120.1 . . ? C12 C11 S1 110.97(13) . . ? C12 C11 C15 126.92(16) . . ? C15 C11 S1 121.55(13) . . ? C11 C12 C3 127.32(16) . . ? C11 C12 C13 111.66(16) . . ? C13 C12 C3 121.02(16) . . ? C12 C13 H13 123.1 . . ? C14 C13 C12 113.81(17) . . ? C14 C13 H13 123.1 . . ? S1 C14 H14 124.3 . . ? C13 C14 S1 111.39(13) . . ? C13 C14 H14 124.3 . . ? N2 C15 C11 126.20(15) . . ? N3 C15 C11 120.99(15) . . ? N3 C15 N2 112.81(15) . . ? C15 N2 C16 106.32(14) . . ? C15 N2 C22 129.63(15) . . ? C16 N2 C22 124.03(15) . . ? C15 N3 C21 105.16(14) . . ? N2 C16 C17 131.42(16) . . ? N2 C16 C21 105.91(15) . . ? C17 C16 C21 122.63(16) . . ? C16 C17 H17 121.9 . . ? C18 C17 C16 116.10(17) . . ? C18 C17 H17 121.9 . . ? C17 C18 H18 119.0 . . ? C17 C18 C19 121.96(17) . . ? C19 C18 H18 119.0 . . ? C18 C19 H19 119.2 . . ? C20 C19 C18 121.56(17) . . ? C20 C19 H19 119.2 . . ? C19 C20 H20 121.3 . . ? C19 C20 C21 117.32(17) . . ? C21 C20 H20 121.3 . . ? N3 C21 C16 109.78(15) . . ? N3 C21 C20 129.79(16) . . ? C20 C21 C16 120.42(16) . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C11 1.7321(17) . ? S1 C14 1.712(2) . ? N1 C1 1.405(2) . ? N1 C4 1.394(2) . ? N1 C5 1.437(2) . ? C1 C2 1.510(2) . ? C1 O1 1.208(2) . ? C2 H2A 0.936(18) . ? C2 H2B 0.936(19) . ? C2 C3 1.532(2) . ? C3 H3 0.95(3) . ? C3 C4 1.527(2) . ? C3 C12 1.513(2) . ? C4 O2 1.208(2) . ? C5 C6 1.386(3) . ? C5 C10 1.392(3) . ? C6 H6 0.95(3) . ? C6 C7 1.395(3) . ? C7 H7 0.95(3) . ? C7 C8 1.383(3) . ? C8 H8 0.97(3) . ? C8 C9 1.390(3) . ? C9 H9 0.99(3) . ? C9 C10 1.388(3) . ? C10 H10 0.99(3) . ? C11 C12 1.384(3) . ? C11 C15 1.459(2) . ? C12 C13 1.421(2) . ? C13 H13 0.99(3) . ? C13 C14 1.360(3) . ? C14 H14 0.96(3) . ? C15 N2 1.380(2) . ? C15 N3 1.322(2) . ? N2 C16 1.380(2) . ? N2 C22 1.463(2) . ? N3 C21 1.387(2) . ? C16 C17 1.400(2) . ? C16 C21 1.402(2) . ? C17 H17 0.96(3) . ? C17 C18 1.384(3) . ? C18 H18 0.96(3) . ? C18 C19 1.408(3) . ? C19 H19 1.01(3) . ? C19 C20 1.386(3) . ? C20 H20 0.94(3) . ? C20 C21 1.400(2) . ? C22 H22A 0.953(17) . ? C22 H22B 0.953(16) . ? C22 H22C 0.953(16) . ? 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 S1 C11 C12 C3 -179.49(15) . . . . ? S1 C11 C12 C13 -0.1(2) . . . . ? S1 C11 C15 N2 -37.9(2) . . . . ? S1 C11 C15 N3 141.44(15) . . . . ? N1 C1 C2 C3 2.73(19) . . . . ? N1 C5 C6 C7 175.27(17) . . . . ? N1 C5 C10 C9 -176.35(16) . . . . ? C1 N1 C4 C3 5.7(2) . . . . ? C1 N1 C4 O2 -176.65(17) . . . . ? C1 N1 C5 C6 -54.7(2) . . . . ? C1 N1 C5 C10 121.34(18) . . . . ? C1 C2 C3 C4 0.52(18) . . . . ? C1 C2 C3 C12 125.34(16) . . . . ? C2 C3 C4 N1 -3.63(19) . . . . ? C2 C3 C4 O2 178.71(18) . . . . ? C2 C3 C12 C11 -43.6(3) . . . . ? C2 C3 C12 C13 137.09(17) . . . . ? C3 C12 C13 C14 179.52(17) . . . . ? C4 N1 C1 C2 -5.3(2) . . . . ? C4 N1 C1 O1 174.88(18) . . . . ? C4 N1 C5 C6 147.12(17) . . . . ? C4 N1 C5 C10 -36.9(2) . . . . ? C4 C3 C12 C11 77.7(2) . . . . ? C4 C3 C12 C13 -101.64(19) . . . . ? O1 C1 C2 C3 -177.48(18) . . . . ? C5 N1 C1 C2 -165.65(15) . . . . ? C5 N1 C1 O1 14.5(3) . . . . ? C5 N1 C4 C3 165.86(15) . . . . ? C5 N1 C4 O2 -16.5(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C5 C10 C9 -0.3(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C10 -1.2(3) . . . . ? C8 C9 C10 C5 1.3(3) . . . . ? C10 C5 C6 C7 -0.7(3) . . . . ? C11 S1 C14 C13 -0.01(16) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C11 C15 N2 C16 179.15(17) . . . . ? C11 C15 N2 C22 0.6(3) . . . . ? C11 C15 N3 C21 179.95(15) . . . . ? C12 C3 C4 N1 -132.55(15) . . . . ? C12 C3 C4 O2 49.8(2) . . . . ? C12 C11 C15 N2 151.39(18) . . . . ? C12 C11 C15 N3 -29.2(3) . . . . ? C12 C13 C14 S1 0.0(2) . . . . ? C14 S1 C11 C12 0.06(14) . . . . ? C14 S1 C11 C15 -171.98(15) . . . . ? C15 C11 C12 C3 -8.0(3) . . . . ? C15 C11 C12 C13 171.42(17) . . . . ? C15 N2 C16 C17 178.89(19) . . . . ? C15 N2 C16 C21 0.99(18) . . . . ? C15 N3 C21 C16 1.23(19) . . . . ? C15 N3 C21 C20 -177.84(19) . . . . ? N2 C15 N3 C21 -0.6(2) . . . . ? N2 C16 C17 C18 -177.21(19) . . . . ? N2 C16 C21 N3 -1.40(19) . . . . ? N2 C16 C21 C20 177.77(17) . . . . ? N3 C15 N2 C16 -0.3(2) . . . . ? N3 C15 N2 C22 -178.86(17) . . . . ? C16 C17 C18 C19 -0.1(3) . . . . ? C17 C16 C21 N3 -179.52(16) . . . . ? C17 C16 C21 C20 -0.4(3) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C21 0.2(3) . . . . ? C19 C20 C21 N3 179.03(17) . . . . ? C19 C20 C21 C16 0.0(3) . . . . ? C21 C16 C17 C18 0.4(3) . . . . ? C22 N2 C16 C17 -2.4(3) . . . . ? C22 N2 C16 C21 179.69(16) . . . . ? 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 -1.0005 1.0004 0.0009 0.1139 0.1071 0.0412 -1.0008 -1.0004 0.0010 0.1285 -0.0977 0.0094 0.0011 -0.0009 0.9998 -0.0051 0.0238 -0.1565 5.0059 1.0007 -1.0028 -0.6087 0.0549 0.0455 5.0036 -4.9969 -1.0069 -0.5646 -0.5592 -0.0493 -0.0002 1.0005 0.0002 -0.0073 0.1024 0.0159 0.0000 0.0000 -1.0000 0.0049 -0.0239 0.1565