#------------------------------------------------------------------------------ #$Date: 2016-05-06 03:44:14 +0300 (Fri, 06 May 2016) $ #$Revision: 182633 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224792.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_7224792 loop_ _publ_author_name 'Zielinski, Witold' 'Katrusiak, Andrzej' _publ_section_title ; Pressure-induced preference for solvation of 5,6-dimethylbenzimidazole ; _journal_issue 18 _journal_name_full CrystEngComm _journal_page_first 3211 _journal_paper_doi 10.1039/C6CE00419A _journal_volume 18 _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 114.720(12) _cell_angle_beta 94.61(2) _cell_angle_gamma 90.202(19) _cell_formula_units_Z 2 _cell_length_a 10.110(6) _cell_length_b 7.1000(7) _cell_length_c 6.6984(10) _cell_measurement_reflns_used 646 _cell_measurement_temperature 296 _cell_measurement_theta_max 25.7930 _cell_measurement_theta_min 3.9490 _cell_volume 435.0(3) _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 16.2413 _diffrn_measured_fraction_theta_full 0.248 _diffrn_measured_fraction_theta_max 0.233 _diffrn_measurement_details ; 1 phi -35.00 19.60 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 78 2 phi 140.00 199.50 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 85 3 phi 160.00 216.70 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 81 4 phi -20.00 34.60 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 78 5 omega -24.00 23.60 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 -12.9000 68 6 omega -24.00 23.60 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 167.1000 68 7 omega -50.00 9.50 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 167.1000 85 8 omega -50.00 9.50 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 -12.9000 85 9 omega -64.00 -8.00 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 -28.9000 80 10 omega -64.00 -8.00 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 151.1000 80 11 omega -19.00 7.60 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 151.1000 38 12 omega -19.00 7.60 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 -28.9000 38 13 omega -43.00 -21.30 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 -56.9000 31 14 omega -43.00 -21.30 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 123.1000 31 15 omega -90.00 -36.10 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 123.1000 77 16 omega -90.00 -36.10 0.7000 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 -56.9000 77 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w and \p scans' _diffrn_orient_matrix_UB_11 -0.0680039000 _diffrn_orient_matrix_UB_12 0.0098580000 _diffrn_orient_matrix_UB_13 -0.0278791000 _diffrn_orient_matrix_UB_21 -0.0173033000 _diffrn_orient_matrix_UB_22 -0.0184067000 _diffrn_orient_matrix_UB_23 0.0910283000 _diffrn_orient_matrix_UB_31 0.0061986000 _diffrn_orient_matrix_UB_32 0.1080734000 _diffrn_orient_matrix_UB_33 0.0680958000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_unetI/netI 0.0302 _diffrn_reflns_Laue_measured_fraction_full 0.248 _diffrn_reflns_Laue_measured_fraction_max 0.233 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2321 _diffrn_reflns_point_group_measured_fraction_full 0.248 _diffrn_reflns_point_group_measured_fraction_max 0.233 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.877 _diffrn_reflns_theta_min 3.972 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.55066 _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_density_diffrn 1.361 _exptl_crystal_description plate _exptl_crystal_F_000 192 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.185 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 437 _refine_ls_number_restraints 186 _refine_ls_restrained_S_all 0.910 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0631 _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^)+(0.1228P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1619 _refine_ls_wR_factor_ref 0.1812 _reflns_Friedel_coverage 0.000 _reflns_number_gt 324 _reflns_number_total 437 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00419a2.cif _cod_data_source_block dMBzIm_MeOH_1_53GPa _cod_depositor_comments 'Adding full bibliography for 7224786--7224795.cif.' _cod_database_code 7224792 _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 23.76 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.82 _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 All non-hydrogen atoms 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(C8) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.2 and sigma for terminal atoms of 0.3 4.a Aromatic/amide H refined with riding coordinates: N1(H1), C2(H2), C7(H7), C4(H4) 4.b Fitted hexagon refined as free rotating group: C9(C8,C7,C6,C5,C4) 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 in P-1 #2 REM reset to P-1 #2 CELL 0.71073 10.110174 7.10002 6.698442 114.72 94.6097 90.2021 ZERR 2 0.005542 0.000701 0.000952 0.0116 0.0233 0.0189 LATT 1 SFAC C H N O UNIT 20 28 4 2 DELU SIMU ISOR 0.2 0.3 C8 C5 C12 C4 N3 C6 C7 C2 C9 O1 C11 N1 C10 L.S. 47 PLAN 5 BOND MORE -1 BOND $H CONF fmap 2 acta 52 OMIT -1 3 2 OMIT 1 1 3 OMIT 0 1 3 OMIT -3 -4 5 OMIT -1 -5 2 OMIT -4 2 5 OMIT -2 -7 3 OMIT -1 -2 4 OMIT -1 1 7 REM REM REM WGHT 0.122800 0.051200 FVAR 10.95832 O1 4 0.580937 0.702499 0.665360 11.00000 0.10637 0.03107 = 0.05155 0.01752 0.02903 -0.00773 AFIX 147 H1A 2 0.597759 0.815406 0.664974 11.00000 -1.50000 AFIX 0 C12 1 0.488807 0.726827 0.822810 11.00000 0.09156 0.03882 = 0.05709 0.01672 0.02324 0.00207 AFIX 137 H12A 2 0.454975 0.592836 0.802261 11.00000 -1.50000 H12B 2 0.416739 0.807162 0.803705 11.00000 -1.50000 H12C 2 0.532423 0.796929 0.968908 11.00000 -1.50000 AFIX 0 N1 3 0.695309 0.353726 0.657979 11.00000 0.05586 0.03354 = 0.04167 0.02353 0.01364 0.00392 AFIX 43 H1 2 0.665803 0.455371 0.631785 11.00000 -1.20000 AFIX 0 N3 3 0.699113 0.064900 0.715214 11.00000 0.06308 0.02880 = 0.04211 0.01950 0.01461 0.00994 C2 1 0.620832 0.199566 0.669570 11.00000 0.05247 0.04078 = 0.03519 0.01511 0.01217 -0.00020 AFIX 43 H2 2 0.528586 0.187810 0.649003 11.00000 -1.20000 AFIX 66 C9 1 0.829692 0.136619 0.732513 11.00000 0.06216 0.02214 = 0.03022 0.01467 0.01205 0.00646 C8 1 0.831920 0.316118 0.697334 11.00000 0.05531 0.02479 = 0.02578 0.00955 0.01689 0.00595 C7 1 0.952516 0.414150 0.704041 11.00000 0.06131 0.02348 = 0.02218 0.00688 0.01360 -0.01249 AFIX 43 H7 2 0.954006 0.534247 0.680503 11.00000 -1.20000 AFIX 65 C6 1 1.070884 0.332683 0.745928 11.00000 0.06087 0.03365 = 0.03387 0.01218 0.01596 -0.00414 C5 1 1.068658 0.153185 0.781108 11.00000 0.06040 0.03608 = 0.02232 0.01036 0.01834 0.00464 C4 1 0.948063 0.055150 0.774401 11.00000 0.05551 0.02407 = 0.02751 0.01071 0.01498 -0.00204 AFIX 43 H4 2 0.946573 -0.064947 0.797938 11.00000 -1.20000 AFIX 0 C10 1 1.193510 0.073438 0.833424 11.00000 0.05845 0.05281 = 0.04201 0.02504 0.00385 -0.00572 AFIX 137 H10A 2 1.253029 0.057196 0.723161 11.00000 -1.50000 H10B 2 1.176453 -0.058497 0.836215 11.00000 -1.50000 H10C 2 1.233046 0.169242 0.975255 11.00000 -1.50000 AFIX 0 C11 1 1.196325 0.438806 0.745625 11.00000 0.06666 0.04946 = 0.03733 0.01920 0.00173 -0.01359 AFIX 137 H11A 2 1.242068 0.351912 0.621378 11.00000 -1.50000 H11B 2 1.251065 0.466388 0.879520 11.00000 -1.50000 H11C 2 1.177570 0.567259 0.735779 11.00000 -1.50000 AFIX 0 HKLF 4 REM 34parok in P-1 #2 REM R1 = 0.0631 for 324 Fo > 4sig(Fo) and 0.0834 for all 437 data REM 110 parameters refined using 186 restraints END WGHT 0.1228 0.0512 REM Highest difference peak 0.185, deepest hole -0.129, 1-sigma level 0.045 Q1 1 1.0000 0.5000 1.0000 10.50000 0.05 0.19 Q2 1 1.2331 0.5564 1.0311 11.00000 0.05 0.18 Q3 1 1.2170 0.3377 0.4419 11.00000 0.05 0.18 Q4 1 0.8956 -0.2066 0.5571 11.00000 0.05 0.16 Q5 1 0.9284 -0.0520 0.5007 11.00000 0.05 0.15 ; _shelx_res_checksum 81717 _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 0.5809(12) 0.7025(5) 0.6654(7) 0.062(10) Uani 1 1 d . U H1A H 0.5978 0.8154 0.6650 0.092 Uiso 1 1 calc GR . C12 C 0.489(2) 0.7268(9) 0.8228(13) 0.063(14) Uani 1 1 d . U H12A H 0.4550 0.5928 0.8023 0.094 Uiso 1 1 calc GR . H12B H 0.4167 0.8072 0.8037 0.094 Uiso 1 1 calc GR . H12C H 0.5324 0.7969 0.9689 0.094 Uiso 1 1 calc GR . N1 N 0.695(2) 0.3537(11) 0.6580(14) 0.041(8) Uani 1 1 d . U H1 H 0.6658 0.4554 0.6318 0.049 Uiso 1 1 calc R . N3 N 0.6991(19) 0.0649(8) 0.7152(10) 0.042(9) Uani 1 1 d . U C2 C 0.621(2) 0.1996(9) 0.6696(15) 0.043(9) Uani 1 1 d . U H2 H 0.5286 0.1878 0.6490 0.051 Uiso 1 1 calc R . C9 C 0.8297(11) 0.1366(8) 0.7325(8) 0.036(9) Uani 1 1 d . U C8 C 0.8319(11) 0.3161(9) 0.6973(10) 0.035(8) Uani 1 1 d G U C7 C 0.9525(12) 0.4142(5) 0.7040(7) 0.036(8) Uani 1 1 d G U H7 H 0.9540 0.5342 0.6805 0.043 Uiso 1 1 calc R . C6 C 1.0709(11) 0.3327(7) 0.7459(8) 0.043(8) Uani 1 1 d G U C5 C 1.0687(11) 0.1532(8) 0.7811(11) 0.039(9) Uani 1 1 d G U C4 C 0.9481(12) 0.0552(6) 0.7744(9) 0.035(9) Uani 1 1 d G U H4 H 0.9466 -0.0649 0.7979 0.042 Uiso 1 1 calc R . C10 C 1.194(2) 0.0734(12) 0.8334(18) 0.049(9) Uani 1 1 d . U H10A H 1.2530 0.0572 0.7232 0.074 Uiso 1 1 calc GR . H10B H 1.1765 -0.0585 0.8362 0.074 Uiso 1 1 calc GR . H10C H 1.2330 0.1692 0.9753 0.074 Uiso 1 1 calc GR . C11 C 1.1963(19) 0.4388(9) 0.7456(12) 0.051(9) Uani 1 1 d . U H11A H 1.2421 0.3519 0.6214 0.077 Uiso 1 1 calc GR . H11B H 1.2511 0.4664 0.8795 0.077 Uiso 1 1 calc GR . H11C H 1.1776 0.5673 0.7358 0.077 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 0.11(3) 0.0311(18) 0.052(3) 0.0175(18) 0.029(8) -0.008(4) C12 0.09(4) 0.039(3) 0.057(5) 0.017(3) 0.023(14) 0.002(7) N1 0.06(2) 0.034(3) 0.042(5) 0.024(3) 0.014(9) 0.004(7) N3 0.06(3) 0.029(2) 0.042(4) 0.020(2) 0.015(9) 0.010(6) C2 0.05(2) 0.041(4) 0.035(5) 0.015(3) 0.012(11) 0.000(8) C9 0.06(2) 0.022(4) 0.030(6) 0.015(3) 0.012(13) 0.006(10) C8 0.06(2) 0.025(3) 0.026(5) 0.010(3) 0.017(10) 0.006(8) C7 0.06(2) 0.023(3) 0.022(4) 0.007(2) 0.014(8) -0.012(6) C6 0.06(2) 0.034(3) 0.034(5) 0.012(3) 0.016(9) -0.004(8) C5 0.06(3) 0.036(4) 0.022(5) 0.010(3) 0.018(10) 0.005(8) C4 0.06(2) 0.024(3) 0.028(5) 0.011(3) 0.015(10) -0.002(8) C10 0.06(3) 0.053(5) 0.042(6) 0.025(4) 0.004(12) -0.006(10) C11 0.07(2) 0.049(3) 0.037(4) 0.019(3) 0.002(9) -0.014(8) 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 126.2 C2 N1 C8 107.5(14) C8 N1 H1 126.2 C2 N3 C9 106.5(7) N1 C2 H2 124.5 N3 C2 N1 110.9(19) N3 C2 H2 124.5 C8 C9 N3 109.9(7) C8 C9 C4 120.0 C4 C9 N3 130.1(7) C9 C8 N1 105.1(6) C9 C8 C7 120.0 C7 C8 N1 134.9(6) C8 C7 H7 120.0 C6 C7 C8 120.0 C6 C7 H7 120.0 C7 C6 C11 118.1(7) C5 C6 C7 120.0 C5 C6 C11 121.9(7) C6 C5 C4 120.0 C6 C5 C10 119.5(6) C4 C5 C10 120.5(6) C9 C4 H4 120.0 C5 C4 C9 120.0 C5 C4 H4 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 1.420(12) C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 N1 H1 0.8600 N1 C2 1.359(11) N1 C8 1.43(2) N3 C2 1.36(2) N3 C9 1.392(18) C2 H2 0.9300 C9 C8 1.3900 C9 C4 1.3900 C8 C7 1.3900 C7 H7 0.9300 C7 C6 1.3900 C6 C5 1.3900 C6 C11 1.473(15) C5 C4 1.3900 C5 C10 1.46(2) C4 H4 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 C7 C6 -179.3(9) N3 C9 C8 N1 0.3(5) N3 C9 C8 C7 -179.2(4) N3 C9 C4 C5 179.0(5) C2 N1 C8 C9 -0.4(7) C2 N1 C8 C7 179.0(4) C2 N3 C9 C8 0.0(4) C2 N3 C9 C4 -179.1(5) C9 N3 C2 N1 -0.3(7) C9 C8 C7 C6 0.0 C8 N1 C2 N3 0.4(8) C8 C9 C4 C5 0.0 C8 C7 C6 C5 0.0 C8 C7 C6 C11 178.4(4) C7 C6 C5 C4 0.0 C7 C6 C5 C10 -177.7(8) C6 C5 C4 C9 0.0 C4 C9 C8 N1 179.5(7) C4 C9 C8 C7 0.0 C10 C5 C4 C9 177.6(8) C11 C6 C5 C4 -178.4(4) C11 C6 C5 C10 4.0(7)