#------------------------------------------------------------------------------ #$Date: 2016-05-06 03:44:14 +0300 (Fri, 06 May 2016) $ #$Revision: 182633 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224793.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_7224793 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 mixed _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 115.381(14) _cell_angle_beta 94.711(14) _cell_angle_gamma 90.103(14) _cell_formula_units_Z 2 _cell_length_a 10.037(2) _cell_length_b 7.0477(10) _cell_length_c 6.6292(10) _cell_measurement_reflns_used 951 _cell_measurement_temperature 296 _cell_measurement_theta_max 28.1771 _cell_measurement_theta_min 3.1956 _cell_volume 421.88(13) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _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 0.292 _diffrn_measured_fraction_theta_max 0.250 _diffrn_measurement_details ; 1 phi -35.00 19.75 0.7500 26.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 73 2 phi 140.00 200.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 80 3 phi 160.00 217.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 76 4 phi -20.00 34.75 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 73 5 omega -24.00 24.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 -12.9000 64 6 omega -24.00 24.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 167.1000 64 7 omega -50.00 10.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 167.1000 80 8 omega -50.00 10.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 -12.9000 80 9 omega -64.00 -8.50 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 -28.9000 74 10 omega -64.00 -8.50 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 151.1000 74 11 omega -19.00 8.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 151.1000 36 12 omega -19.00 8.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 -28.9000 36 13 omega -43.00 -21.25 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 -56.9000 29 14 omega -43.00 -21.25 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 123.1000 29 15 omega -90.00 -36.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 123.1000 72 16 omega -90.00 -36.00 0.7500 28.0000 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 -0.0357841000 _diffrn_orient_matrix_UB_12 0.0307435000 _diffrn_orient_matrix_UB_13 0.0575599000 _diffrn_orient_matrix_UB_21 0.0178374000 _diffrn_orient_matrix_UB_22 -0.0782565000 _diffrn_orient_matrix_UB_23 0.0366686000 _diffrn_orient_matrix_UB_31 0.1120064000 _diffrn_orient_matrix_UB_32 0.0732156000 _diffrn_orient_matrix_UB_33 0.0194639000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1170 _diffrn_reflns_av_unetI/netI 0.0694 _diffrn_reflns_Laue_measured_fraction_full 0.292 _diffrn_reflns_Laue_measured_fraction_max 0.250 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2970 _diffrn_reflns_point_group_measured_fraction_full 0.292 _diffrn_reflns_point_group_measured_fraction_max 0.250 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.239 _diffrn_reflns_theta_min 3.202 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.40172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) 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 1.403 _exptl_crystal_description plate _exptl_crystal_F_000 192 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.187 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 114 _refine_ls_number_reflns 520 _refine_ls_number_restraints 78 _refine_ls_restrained_S_all 0.996 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0612 _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^)+(0.0900P)^2^+0.2957P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1529 _refine_ls_wR_factor_ref 0.1813 _reflns_Friedel_coverage 0.000 _reflns_number_gt 355 _reflns_number_total 520 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00419a2.cif _cod_data_source_block dMBzIm_MeOH_1_90GPa _cod_depositor_comments 'Adding full bibliography for 7224786--7224795.cif.' _cod_database_code 7224793 _chemical_oxdiff_formula 'C11 H10 N O' _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 28.24 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C9) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01 3.a Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C7(H7) 3.b Fitted hexagon refined as free rotating group: C4(C9,C8,C7,C6,C5) 3.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C) 3.d Idealised tetrahedral OH refined as rotating group: O1(H1A) ; _shelx_res_file ; 36_15.res created by SHELXL-2014/7 TITL 36_15 in P1 #1 REM reset to P1 #1 CELL 0.71073 10.036893 7.047701 6.629183 115.3808 94.7109 90.1028 ZERR 2 0.002077 0.000971 0.000958 0.0139 0.0142 0.0137 LATT 1 SFAC C H N O UNIT 20 28 4 2 ISOR 0.01 0.01 C9 C12 C7 N3 C10 C4 C6 C2 O1 C5 N1 C11 C8 L.S. 44 PLAN 5 BOND MORE -1 CONF fmap 2 acta BOND $H OMIT 0 0 5 OMIT -1 2 5 OMIT -1 6 3 OMIT -3 2 1 OMIT 1 -1 2 OMIT 2 -3 1 OMIT 7 -2 5 REM REM REM WGHT 0.090000 0.295700 FVAR 3.57522 O1 4 0.578143 0.703055 0.666913 11.00000 0.05961 0.04128 = 0.05509 0.01837 -0.00439 0.01425 AFIX 147 H1A 2 0.612329 0.817733 0.692224 11.00000 -1.50000 AFIX 0 C12 1 0.491618 0.727551 0.823667 11.00000 0.05555 0.04981 = 0.06363 0.02827 0.00160 0.00605 AFIX 137 H12A 2 0.536316 0.804609 0.970895 11.00000 -1.50000 H12B 2 0.461318 0.591971 0.807217 11.00000 -1.50000 H12C 2 0.416295 0.803323 0.803263 11.00000 -1.50000 AFIX 0 N1 3 0.699173 0.355981 0.655081 11.00000 0.04428 0.03358 = 0.04923 0.01782 -0.00979 0.00569 H1 2 0.651550 0.472744 0.655677 11.00000 0.06014 N3 3 0.694756 0.065458 0.715821 11.00000 0.04740 0.03817 = 0.03710 0.01875 -0.00442 0.00519 C2 1 0.622078 0.203547 0.671448 11.00000 0.04546 0.04369 = 0.03883 0.02099 -0.00951 0.00201 AFIX 43 H2 2 0.529054 0.197028 0.653547 11.00000 -1.20000 AFIX 66 C4 1 0.944684 0.054548 0.775224 11.00000 0.03325 0.02150 = 0.03336 0.01550 -0.00348 -0.00263 AFIX 43 H4 2 0.944798 -0.065935 0.799623 11.00000 -1.20000 AFIX 65 C9 1 0.824202 0.133686 0.733058 11.00000 0.02866 0.02781 = 0.03399 0.01018 -0.00426 0.00029 C8 1 0.824032 0.313763 0.696591 11.00000 0.02927 0.03317 = 0.03286 0.01457 -0.00532 0.00002 C7 1 0.944343 0.414703 0.702289 11.00000 0.03772 0.03289 = 0.04066 0.01191 -0.00738 0.00867 AFIX 43 H7 2 0.944229 0.535186 0.677889 11.00000 -1.20000 AFIX 65 C6 1 1.064826 0.335566 0.744454 11.00000 0.03274 0.02878 = 0.03336 0.01567 -0.00641 -0.01379 C5 1 1.064999 0.155490 0.780922 11.00000 0.02197 0.02635 = 0.03275 0.01071 -0.00951 -0.00576 AFIX 0 C10 1 1.196920 0.073325 0.831750 11.00000 0.04588 0.05504 = 0.04013 0.02039 -0.00520 0.01229 AFIX 137 H10A 2 1.182357 -0.065859 0.819967 11.00000 -1.50000 H10B 2 1.233691 0.164243 0.981022 11.00000 -1.50000 H10C 2 1.258240 0.069566 0.726445 11.00000 -1.50000 AFIX 0 C11 1 1.196542 0.439591 0.739757 11.00000 0.04178 0.04051 = 0.04228 0.01289 -0.00139 -0.00247 AFIX 137 H11A 2 1.248818 0.480966 0.880987 11.00000 -1.50000 H11B 2 1.179104 0.561380 0.713453 11.00000 -1.50000 H11C 2 1.244917 0.342147 0.621862 11.00000 -1.50000 AFIX 0 HKLF 4 REM 36_15 in P1 #1 REM R1 = 0.0612 for 355 Fo > 4sig(Fo) and 0.0925 for all 520 data REM 114 parameters refined using 78 restraints END WGHT 0.0900 0.2957 REM Highest difference peak 0.187, deepest hole -0.162, 1-sigma level 0.045 Q1 1 0.3962 0.5767 0.6870 11.00000 0.05 0.19 Q2 1 0.5445 0.9959 0.7864 11.00000 0.05 0.15 Q3 1 0.5255 0.2510 0.7577 11.00000 0.05 0.14 Q4 1 0.6236 0.7346 1.1434 11.00000 0.05 0.14 Q5 1 0.8794 0.5181 0.6112 11.00000 0.05 0.13 ; _shelx_res_checksum 74006 _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 0.5781(11) 0.7031(8) 0.6669(9) 0.053(5) Uani 1 1 d . U H1A H 0.6123 0.8177 0.6922 0.080 Uiso 1 1 calc GR . C12 C 0.4916(19) 0.7276(15) 0.8237(15) 0.055(6) Uani 1 1 d . U H12A H 0.5363 0.8046 0.9709 0.083 Uiso 1 1 calc GR . H12B H 0.4613 0.5920 0.8072 0.083 Uiso 1 1 calc GR . H12C H 0.4163 0.8033 0.8033 0.083 Uiso 1 1 calc GR . N1 N 0.6992(12) 0.3560(10) 0.6551(10) 0.043(5) Uani 1 1 d . U H1 H 0.652(12) 0.473(10) 0.656(11) 0.060(19) Uiso 1 1 d . . N3 N 0.6948(12) 0.0655(8) 0.7158(10) 0.040(5) Uani 1 1 d . U C2 C 0.6221(15) 0.2035(11) 0.6714(11) 0.042(5) Uani 1 1 d . U H2 H 0.5291 0.1970 0.6535 0.051 Uiso 1 1 calc R . C4 C 0.9447(7) 0.0545(5) 0.7752(6) 0.028(5) Uani 1 1 d . U H4 H 0.9448 -0.0659 0.7996 0.034 Uiso 1 1 calc R . C9 C 0.8242(7) 0.1337(6) 0.7331(6) 0.032(5) Uani 1 1 d G U C8 C 0.8240(7) 0.3138(6) 0.6966(7) 0.032(5) Uani 1 1 d G U C7 C 0.9443(7) 0.4147(5) 0.7023(7) 0.039(5) Uani 1 1 d G U H7 H 0.9442 0.5352 0.6779 0.047 Uiso 1 1 calc R . C6 C 1.0648(7) 0.3356(6) 0.7445(7) 0.031(5) Uani 1 1 d G U C5 C 1.0650(7) 0.1555(6) 0.7809(6) 0.028(5) Uani 1 1 d G U C10 C 1.1969(14) 0.0733(11) 0.8318(12) 0.048(5) Uani 1 1 d . U H10A H 1.1824 -0.0659 0.8200 0.071 Uiso 1 1 calc GR . H10B H 1.2337 0.1642 0.9810 0.071 Uiso 1 1 calc GR . H10C H 1.2582 0.0696 0.7264 0.071 Uiso 1 1 calc GR . C11 C 1.1965(17) 0.4396(12) 0.7398(13) 0.044(6) Uani 1 1 d . U H11A H 1.2488 0.4810 0.8810 0.065 Uiso 1 1 calc GR . H11B H 1.1791 0.5614 0.7135 0.065 Uiso 1 1 calc GR . H11C H 1.2449 0.3421 0.6219 0.065 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 0.060(10) 0.041(3) 0.055(3) 0.018(2) -0.004(5) 0.014(5) C12 0.056(11) 0.050(4) 0.064(5) 0.028(4) 0.002(7) 0.006(6) N1 0.044(11) 0.034(3) 0.049(4) 0.018(3) -0.010(5) 0.006(5) N3 0.047(11) 0.038(3) 0.037(3) 0.019(2) -0.004(5) 0.005(5) C2 0.045(11) 0.044(4) 0.039(4) 0.021(3) -0.010(6) 0.002(6) C4 0.033(11) 0.021(3) 0.033(4) 0.015(3) -0.003(6) -0.003(5) C9 0.029(11) 0.028(3) 0.034(4) 0.010(3) -0.004(6) 0.000(6) C8 0.029(11) 0.033(4) 0.033(4) 0.015(3) -0.005(6) 0.000(6) C7 0.038(11) 0.033(4) 0.041(4) 0.012(3) -0.007(6) 0.009(5) C6 0.033(11) 0.029(4) 0.033(4) 0.016(3) -0.006(6) -0.014(6) C5 0.022(11) 0.026(4) 0.033(4) 0.011(3) -0.010(6) -0.006(5) C10 0.046(11) 0.055(4) 0.040(4) 0.020(3) -0.005(6) 0.012(6) C11 0.042(11) 0.041(4) 0.042(4) 0.013(3) -0.001(6) -0.002(6) 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 115(9) C8 N1 H1 138(8) C8 N1 C2 105.1(6) C2 N3 C9 104.8(10) N1 C2 H2 123.6 N3 C2 N1 112.7(12) N3 C2 H2 123.6 C9 C4 H4 120.0 C9 C4 C5 120.0 C5 C4 H4 120.0 N3 C9 C4 131.8(4) N3 C9 C8 108.2(4) C4 C9 C8 120.0 N1 C8 C9 109.2(6) N1 C8 C7 130.8(6) C7 C8 C9 120.0 C8 C7 H7 120.0 C6 C7 C8 120.0 C6 C7 H7 120.0 C7 C6 C5 120.0 C7 C6 C11 120.1(4) C5 C6 C11 119.9(4) C4 C5 C10 120.5(6) C6 C5 C4 120.0 C6 C5 C10 119.5(6) 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 1.36(2) C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 N1 H1 0.95(5) N1 C2 1.369(18) N1 C8 1.323(10) N3 C2 1.334(7) N3 C9 1.363(15) C2 H2 0.9300 C4 H4 0.9300 C4 C9 1.3900 C4 C5 1.3900 C9 C8 1.3900 C8 C7 1.3900 C7 H7 0.9300 C7 C6 1.3900 C6 C5 1.3900 C6 C11 1.52(2) C5 C10 1.516(9) 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 -178.2(5) N3 C9 C8 N1 -0.8(4) N3 C9 C8 C7 -179.3(4) C2 N1 C8 C9 1.4(6) C2 N1 C8 C7 179.7(4) C2 N3 C9 C4 -179.4(4) C2 N3 C9 C8 -0.2(5) C4 C9 C8 N1 178.5(4) C4 C9 C8 C7 0.0 C9 N3 C2 N1 1.2(8) C9 C4 C5 C6 0.0 C9 C4 C5 C10 178.7(4) C9 C8 C7 C6 0.0 C8 N1 C2 N3 -1.6(8) C8 C7 C6 C5 0.0 C8 C7 C6 C11 177.1(5) C7 C6 C5 C4 0.0 C7 C6 C5 C10 -178.7(4) C5 C4 C9 N3 179.1(5) C5 C4 C9 C8 0.0 C11 C6 C5 C4 -177.1(5) C11 C6 C5 C10 4.2(5)