#------------------------------------------------------------------------------ #$Date: 2016-04-05 06:25:52 +0300 (Tue, 05 Apr 2016) $ #$Revision: 181491 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224795.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_7224795 loop_ _publ_author_name 'Zielinski, Witold' 'Katrusiak, Andrzej' _publ_section_title ; Pressure-induced preference for solvation of 5,6-dimethylbenzimidazole ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C6CE00419A _journal_year 2016 _chemical_formula_moiety 'C H4 O, C9 H10 N2' _chemical_formula_sum 'C10 H14 N2 O' _chemical_formula_weight 178.23 _chemical_name_common '5,6-dimethylbenzimidazole methanol solvate' _chemical_name_systematic '5,6-dimethylbenzimidazole methanol solvate' _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 direct _audit_creation_date 2016-03-29 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2016-03-29 deposited with the CCDC. 2016-04-01 downloaded from the CCDC. ; _cell_angle_alpha 116.173(19) _cell_angle_beta 94.86(3) _cell_angle_gamma 90.02(4) _cell_formula_units_Z 2 _cell_length_a 10.027(10) _cell_length_b 7.0054(13) _cell_length_c 6.5581(12) _cell_measurement_reflns_used 572 _cell_measurement_temperature 296 _cell_measurement_theta_max 26.6590 _cell_measurement_theta_min 3.2190 _cell_volume 411.6(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 296 _diffrn_detector_area_resol_mean 16.1544 _diffrn_measured_fraction_theta_full 0.241 _diffrn_measured_fraction_theta_max 0.213 _diffrn_measurement_details ; 1 phi -35.00 19.75 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 73 2 phi 140.00 200.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 80 3 phi 160.00 217.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 76 4 phi -20.00 34.75 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 73 5 omega -24.00 24.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 -12.9000 64 6 omega -24.00 24.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 167.1000 64 7 omega -50.00 10.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 167.1000 80 8 omega -50.00 10.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 -12.9000 80 9 omega -64.00 -8.50 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 -28.9000 74 10 omega -64.00 -8.50 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 151.1000 74 11 omega -19.00 8.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 151.1000 36 12 omega -19.00 8.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 -28.9000 36 13 omega -43.00 -21.25 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 -56.9000 29 14 omega -43.00 -21.25 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 123.1000 29 15 omega -90.00 -36.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 123.1000 72 16 omega -90.00 -36.00 0.7500 30.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 -56.9000 72 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w and \p scans' _diffrn_orient_matrix_UB_11 -0.0685872000 _diffrn_orient_matrix_UB_12 0.0134739000 _diffrn_orient_matrix_UB_13 0.0198190000 _diffrn_orient_matrix_UB_21 0.0095557000 _diffrn_orient_matrix_UB_22 -0.0415404000 _diffrn_orient_matrix_UB_23 0.0809182000 _diffrn_orient_matrix_UB_31 0.0159417000 _diffrn_orient_matrix_UB_32 0.1041327000 _diffrn_orient_matrix_UB_33 0.0878292000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1078 _diffrn_reflns_av_unetI/netI 0.0653 _diffrn_reflns_Laue_measured_fraction_full 0.241 _diffrn_reflns_Laue_measured_fraction_max 0.213 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 1828 _diffrn_reflns_point_group_measured_fraction_full 0.241 _diffrn_reflns_point_group_measured_fraction_max 0.213 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.868 _diffrn_reflns_theta_min 3.243 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.41626 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.438 _exptl_crystal_description plate _exptl_crystal_F_000 192 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.189 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 419 _refine_ls_number_restraints 186 _refine_ls_restrained_S_all 0.915 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0757 _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^)+(0.1597P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1960 _refine_ls_wR_factor_ref 0.2366 _reflns_Friedel_coverage 0.000 _reflns_number_gt 277 _reflns_number_total 419 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00419a2.cif _cod_data_source_block dMBzIm_MeOH_2_31GPa _cod_database_code 7224795 _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. ; _reflns_odcompleteness_completeness 21.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.81 _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 C(H,H,H) groups, All O(H) groups 2. Rigid bond restraints O1, C12, N1, N3, C2, C4, C5, C6, C7, C8, C9, C10, C11 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 3. Uiso/Uaniso restraints and constraints All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(C12) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01 4.a Aromatic/amide H refined with riding coordinates: N1(H1), C2(H2), C4(H4), C7(H7) 4.b Fitted hexagon refined as free rotating group: C8(C9,C4,C5,C6,C7) 4.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C) 4.d Idealised tetrahedral OH refined as rotating group: O1(H1A) ; _shelx_res_file ; 34parok.res created by SHELXL-2014/7 TITL 34parok_a.res in P1 REM Old TITL 34 parok in P-1 #2 REM SHELXT solution in P1 REM R1 0.392, Rweak 0.029, Alpha 0.000, Orientation as input REM Flack x = 0.139 ( 3.741 ) from Parsons' quotients REM Formula found by SHELXT: C16 N3 O4 CELL 0.71073 10.026569 7.005354 6.558101 116.1727 94.8619 90.0224 ZERR 2 0.009841 0.00134 0.001153 0.0191 0.0342 0.0379 LATT 1 SFAC C H N O UNIT 20 28 4 2 DELU O1 C12 N1 N3 C2 C4 > C7 C8 C9 C10 C11 SIMU ISOR 0.01 0.01 C12 C2 N1 C8 N3 C7 C9 C6 C4 C5 C11 C10 O1 L.S. 44 PLAN 5 BOND $H LIST 6 MORE -1 CONF fmap 2 acta 52 OMIT 1 -2 4 OMIT 2 1 1 OMIT 2 0 3 OMIT 3 3 2 OMIT 2 4 1 OMIT 1 -7 3 OMIT 3 2 2 OMIT -1 1 2 OMIT 2 6 1 OMIT 1 4 1 OMIT 2 6 0 OMIT 1 6 1 OMIT 2 -2 4 REM REM REM WGHT 0.159700 FVAR 1.37314 O1 4 0.576503 0.704606 0.665273 11.00000 0.03920 0.03387 = 0.04320 0.02505 0.00148 0.00533 AFIX 147 H1A 2 0.609015 0.822069 0.693658 11.00000 -1.50000 AFIX 0 C12 1 0.490927 0.724960 0.828831 11.00000 0.04244 0.04399 = 0.04794 0.02456 0.00337 0.00940 AFIX 137 H12A 2 0.539392 0.789666 0.977473 11.00000 -1.50000 H12B 2 0.455722 0.586780 0.799213 11.00000 -1.50000 H12C 2 0.418504 0.812506 0.822879 11.00000 -1.50000 AFIX 0 N1 3 0.695800 0.354070 0.653800 11.00000 0.03573 0.04226 = 0.03833 0.03119 0.00451 0.01297 AFIX 43 H1 2 0.666425 0.455059 0.623720 11.00000 -1.20000 AFIX 0 N3 3 0.696714 0.064928 0.713750 11.00000 0.02881 0.02875 = 0.02528 0.01457 0.00234 0.00241 C2 1 0.621548 0.203195 0.669873 11.00000 0.03245 0.04095 = 0.03029 0.02252 0.00049 0.00377 AFIX 43 H2 2 0.528387 0.195204 0.652565 11.00000 -1.20000 AFIX 66 C8 1 0.826676 0.317551 0.694059 11.00000 0.03245 0.02338 = 0.02597 0.01427 0.00179 0.00277 C9 1 0.825402 0.138250 0.733516 11.00000 0.02660 0.01845 = 0.02172 0.00933 -0.00025 -0.00067 C4 1 0.945331 0.057681 0.777325 11.00000 0.02957 0.02671 = 0.01875 0.01365 -0.00135 0.00517 AFIX 43 H4 2 0.944478 -0.062284 0.803724 11.00000 -1.20000 AFIX 65 C5 1 1.066535 0.156411 0.781679 11.00000 0.03011 0.02954 = 0.02657 0.01543 -0.00440 0.00382 C6 1 1.067811 0.335711 0.742222 11.00000 0.03193 0.03837 = 0.02494 0.01929 0.00573 0.00485 C7 1 0.947883 0.416284 0.698412 11.00000 0.03028 0.02497 = 0.02635 0.01339 -0.00509 0.00210 AFIX 43 H7 2 0.948737 0.536248 0.672013 11.00000 -1.20000 AFIX 0 C10 1 1.195295 0.075777 0.838473 11.00000 0.02969 0.04276 = 0.03825 0.02328 -0.00274 0.00021 AFIX 137 H10A 2 1.259459 0.074287 0.737181 11.00000 -1.50000 H10B 2 1.180228 -0.065988 0.821635 11.00000 -1.50000 H10C 2 1.228988 0.167185 0.993119 11.00000 -1.50000 AFIX 0 C11 1 1.193880 0.437170 0.740356 11.00000 0.03344 0.04655 = 0.02880 0.02082 0.00836 0.00538 AFIX 137 H11A 2 1.233382 0.351626 0.601901 11.00000 -1.50000 H11B 2 1.253725 0.451406 0.868993 11.00000 -1.50000 H11C 2 1.177798 0.575488 0.748944 11.00000 -1.50000 AFIX 0 HKLF 4 REM 34parok_a.res in P1 REM R1 = 0.0757 for 277 Fo > 4sig(Fo) and 0.1133 for all 419 data REM 110 parameters refined using 186 restraints END WGHT 0.1597 0.0000 REM Highest difference peak 0.189, deepest hole -0.216, 1-sigma level 0.060 Q1 1 1.2919 0.1784 1.0776 11.00000 0.05 0.19 Q2 1 0.5371 0.9221 1.0848 11.00000 0.05 0.19 Q3 1 1.0000 0.0000 1.0000 10.50000 0.05 0.18 Q4 1 0.4339 0.5472 0.9416 11.00000 0.05 0.16 Q5 1 1.3079 0.3590 0.9998 11.00000 0.05 0.16 ; _shelx_res_checksum 51538 _shelx_shelxl_version_number 2014/7 _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_refinement_flags_adp O1 O 0.5765(15) 0.7046(8) 0.6653(10) 0.036(4) Uani 1 1 d . U H1A H 0.6090 0.8221 0.6937 0.054 Uiso 1 1 calc GR . C12 C 0.491(3) 0.7250(13) 0.8288(15) 0.043(5) Uani 1 1 d . U H12A H 0.5394 0.7897 0.9775 0.065 Uiso 1 1 calc GR . H12B H 0.4557 0.5868 0.7992 0.065 Uiso 1 1 calc GR . H12C H 0.4185 0.8125 0.8229 0.065 Uiso 1 1 calc GR . N1 N 0.696(2) 0.3541(11) 0.6538(12) 0.034(4) Uani 1 1 d . U H1 H 0.6664 0.4551 0.6237 0.041 Uiso 1 1 calc R . N3 N 0.6967(19) 0.0649(10) 0.7138(11) 0.027(3) Uani 1 1 d . U C2 C 0.622(2) 0.2032(11) 0.6699(12) 0.032(4) Uani 1 1 d . U H2 H 0.5284 0.1952 0.6526 0.039 Uiso 1 1 calc R . C8 C 0.8267(12) 0.3176(8) 0.6941(9) 0.026(3) Uani 1 1 d . U C9 C 0.8254(12) 0.1383(8) 0.7335(9) 0.022(3) Uani 1 1 d G U C4 C 0.9453(12) 0.0577(6) 0.7773(8) 0.024(3) Uani 1 1 d G U H4 H 0.9445 -0.0623 0.8037 0.029 Uiso 1 1 calc R . C5 C 1.0665(12) 0.1564(8) 0.7817(8) 0.028(3) Uani 1 1 d G U C6 C 1.0678(12) 0.3357(8) 0.7422(9) 0.030(3) Uani 1 1 d G U C7 C 0.9479(12) 0.4163(6) 0.6984(8) 0.027(3) Uani 1 1 d G U H7 H 0.9487 0.5362 0.6720 0.032 Uiso 1 1 calc R . C10 C 1.195(2) 0.0758(12) 0.8385(14) 0.035(4) Uani 1 1 d . U H10A H 1.2595 0.0743 0.7372 0.053 Uiso 1 1 calc GR . H10B H 1.1802 -0.0660 0.8216 0.053 Uiso 1 1 calc GR . H10C H 1.2290 0.1672 0.9931 0.053 Uiso 1 1 calc GR . C11 C 1.194(3) 0.4372(13) 0.7404(14) 0.034(4) Uani 1 1 d . U H11A H 1.2334 0.3516 0.6019 0.052 Uiso 1 1 calc GR . H11B H 1.2537 0.4514 0.8690 0.052 Uiso 1 1 calc GR . H11C H 1.1778 0.5755 0.7489 0.052 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 O1 0.039(12) 0.034(3) 0.043(3) 0.025(3) 0.001(5) 0.005(5) C12 0.042(13) 0.044(5) 0.048(5) 0.025(4) 0.003(7) 0.009(7) N1 0.036(9) 0.042(4) 0.038(4) 0.031(3) 0.005(6) 0.013(6) N3 0.029(9) 0.029(3) 0.025(3) 0.015(3) 0.002(6) 0.002(5) C2 0.032(9) 0.041(4) 0.030(4) 0.023(4) 0.000(7) 0.004(6) C8 0.032(8) 0.023(3) 0.026(4) 0.014(3) 0.002(7) 0.003(6) C9 0.027(8) 0.018(4) 0.022(4) 0.009(3) 0.000(7) -0.001(6) C4 0.030(8) 0.027(4) 0.019(3) 0.014(3) -0.001(7) 0.005(6) C5 0.030(8) 0.030(4) 0.027(4) 0.015(3) -0.004(7) 0.004(6) C6 0.032(8) 0.038(4) 0.025(4) 0.019(3) 0.006(7) 0.005(6) C7 0.030(8) 0.025(3) 0.026(4) 0.013(3) -0.005(7) 0.002(6) C10 0.030(10) 0.043(4) 0.038(4) 0.023(4) -0.003(7) 0.000(7) C11 0.033(9) 0.047(4) 0.029(4) 0.021(4) 0.008(7) 0.005(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 O1 H1A 109.5 O1 C12 H12A 109.5 O1 C12 H12B 109.5 O1 C12 H12C 109.5 H12A C12 H12B 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C2 N1 H1 126.4 C2 N1 C8 107.2(11) C8 N1 H1 126.4 C2 N3 C9 104.7(9) N1 C2 N3 112.4(19) N1 C2 H2 123.8 N3 C2 H2 123.8 N1 C8 C9 105.9(5) N1 C8 C7 134.0(5) C9 C8 C7 120.0 N3 C9 C8 109.8(6) N3 C9 C4 130.1(6) C4 C9 C8 120.0 C9 C4 H4 120.0 C5 C4 C9 120.0 C5 C4 H4 120.0 C4 C5 C6 120.0 C4 C5 C10 120.1(7) C6 C5 C10 119.8(6) C5 C6 C11 120.6(7) C7 C6 C5 120.0 C7 C6 C11 119.4(7) C8 C7 H7 120.0 C6 C7 C8 120.0 C6 C7 H7 120.0 C5 C10 H10A 109.5 C5 C10 H10B 109.5 C5 C10 H10C 109.5 H10A C10 H10B 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C6 C11 H11A 109.5 C6 C11 H11B 109.5 C6 C11 H11C 109.5 H11A C11 H11B 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 H1A 0.8200 O1 C12 1.39(2) C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 N1 H1 0.8600 N1 C2 1.339(18) N1 C8 1.36(2) N3 C2 1.341(17) N3 C9 1.36(2) C2 H2 0.9300 C8 C9 1.3900 C8 C7 1.3900 C9 C4 1.3900 C4 H4 0.9300 C4 C5 1.3900 C5 C6 1.3900 C5 C10 1.49(2) C6 C7 1.3900 C6 C11 1.45(2) C7 H7 0.9300 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 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 N1 C8 C9 N3 1.0(6) N1 C8 C9 C4 179.1(6) N1 C8 C7 C6 -178.8(8) N3 C9 C4 C5 177.6(7) C2 N1 C8 C9 0.2(8) C2 N1 C8 C7 179.1(5) C2 N3 C9 C8 -1.8(7) C2 N3 C9 C4 -179.7(5) C8 N1 C2 N3 -1.4(11) C8 C9 C4 C5 0.0 C9 N3 C2 N1 2.0(10) C9 C8 C7 C6 0.0 C9 C4 C5 C6 0.0 C9 C4 C5 C10 177.4(6) C4 C5 C6 C7 0.0 C4 C5 C6 C11 -178.4(6) C5 C6 C7 C8 0.0 C7 C8 C9 N3 -178.1(6) C7 C8 C9 C4 0.0 C10 C5 C6 C7 -177.4(6) C10 C5 C6 C11 4.2(8) C11 C6 C7 C8 178.4(6)