#------------------------------------------------------------------------------ #$Date: 2016-05-06 03:44:14 +0300 (Fri, 06 May 2016) $ #$Revision: 182633 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224794.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_7224794 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 115.903(19) _cell_angle_beta 94.821(18) _cell_angle_gamma 90.068(19) _cell_formula_units_Z 2 _cell_length_a 10.007(3) _cell_length_b 7.0202(14) _cell_length_c 6.5889(12) _cell_measurement_reflns_used 641 _cell_measurement_temperature 296 _cell_measurement_theta_max 25.3800 _cell_measurement_theta_min 3.2030 _cell_volume 414.53(18) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _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 'CCD plate' _diffrn_detector_area_resol_mean 16.1544 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.262 _diffrn_measured_fraction_theta_max 0.235 _diffrn_measurement_details ; 1 omega 1.00 33.25 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 -53.0000 17.0000 43 2 omega 29.00 78.50 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 -134.0000 -123.0000 66 3 omega -42.00 -6.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 -19.0000 -120.0000 48 4 omega -15.00 39.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 -39.0000 -167.0000 72 5 omega -29.00 -2.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 114.0000 -44.0000 36 6 omega -26.00 1.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -16.6837 19.0000 -180.0000 36 7 omega -37.00 3.50 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -16.6837 53.0000 -17.0000 54 8 omega -6.00 24.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -16.6837 -97.0000 35.0000 40 9 omega -44.25 42.00 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 -37.0000 30.0000 115 10 omega -47.00 -3.50 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 134.0000 123.0000 58 11 omega -10.00 34.25 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - 15.7462 37.0000 150.0000 59 12 omega -80.00 -3.50 0.7500 28.0000 omega____ theta____ kappa____ phi______ frames - -16.6837 134.0000 -56.0000 102 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0342737000 _diffrn_orient_matrix_UB_12 0.0309177000 _diffrn_orient_matrix_UB_13 0.0582974000 _diffrn_orient_matrix_UB_21 0.0181260000 _diffrn_orient_matrix_UB_22 -0.0788279000 _diffrn_orient_matrix_UB_23 0.0362600000 _diffrn_orient_matrix_UB_31 0.1137824000 _diffrn_orient_matrix_UB_32 0.0739519000 _diffrn_orient_matrix_UB_33 0.0188554000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_unetI/netI 0.0450 _diffrn_reflns_Laue_measured_fraction_full 0.262 _diffrn_reflns_Laue_measured_fraction_max 0.235 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2019 _diffrn_reflns_point_group_measured_fraction_full 0.262 _diffrn_reflns_point_group_measured_fraction_max 0.235 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.500 _diffrn_reflns_theta_min 3.229 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.01010 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) 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 1.428 _exptl_crystal_description plate _exptl_crystal_F_000 192 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.163 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 449 _refine_ls_number_restraints 186 _refine_ls_restrained_S_all 0.874 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0525 _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^)+(0.0910P)^2^+0.2100P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1324 _refine_ls_wR_factor_ref 0.1587 _reflns_Friedel_coverage 0.000 _reflns_number_gt 312 _reflns_number_total 449 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00419a2.cif _cod_data_source_block dMBzIm_MeOH_2_19GPa _cod_depositor_comments 'Adding full bibliography for 7224786--7224795.cif.' _cod_original_cell_volume 414.53(17) _cod_database_code 7224794 _chemical_oxdiff_formula 'C10 H14 N2 O1' _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 27.51 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 25.30 _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, N1, N3, C2, C4, C5, C6, C7, C8, C9, C10, C11, C12 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 3. Uiso/Uaniso restraints and constraints O1 \\sim N1 \\sim N3 \\sim C2 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(N1) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C12) \\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: C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C) 4.d Idealised tetrahedral OH refined as rotating group: O1(H1A) ; _shelx_res_file ; 35.res created by SHELXL-2014/7 TITL 35 in P-1 #2 REM reset to P-1 #2 CELL 0.71073 10.00694 7.020249 6.588892 115.9034 94.8212 90.0683 ZERR 2 0.002543 0.00143 0.001203 0.019 0.0178 0.0185 LATT 1 SFAC C H N O UNIT 20 28 4 2 DELU O1 > C2 C4 > C7 C8 C9 C10 > C12 SIMU O1 > C2 C4 > C7 C8 C9 C10 > C12 ISOR 0.01 0.01 N1 N3 C9 C2 C8 C4 C7 C5 C6 C10 C11 O1 C12 L.S. 44 PLAN 5 BOND MORE -1 CONF fmap 2 acta 52 BOND $H OMIT 5 -6 4 OMIT -2 5 1 REM REM REM WGHT 0.091000 0.210000 FVAR 3.60854 O1 4 0.577667 0.704250 0.664683 11.00000 0.04372 0.02880 = 0.04172 0.01285 0.00131 0.00960 AFIX 147 H1A 2 0.615020 0.819225 0.696953 11.00000 -1.50000 AFIX 0 N1 3 0.697331 0.354114 0.656495 11.00000 0.02829 0.02712 = 0.03283 0.01652 -0.00180 0.00373 AFIX 43 H1 2 0.668767 0.455752 0.627204 11.00000 -1.20000 AFIX 0 N3 3 0.694567 0.065264 0.717161 11.00000 0.02762 0.02722 = 0.02785 0.01521 0.00349 0.00463 C2 1 0.620949 0.203248 0.672105 11.00000 0.02899 0.02809 = 0.03843 0.01328 -0.00395 -0.00077 AFIX 43 H2 2 0.527627 0.196169 0.653587 11.00000 -1.20000 AFIX 66 C8 1 0.826455 0.315987 0.695264 11.00000 0.01954 0.02032 = 0.02635 0.00530 -0.00944 0.00217 C9 1 0.826593 0.135560 0.732123 11.00000 0.02333 0.02219 = 0.02341 0.00808 0.00123 -0.00014 C4 1 0.947448 0.056433 0.774960 11.00000 0.02512 0.01692 = 0.02178 0.01327 0.00249 0.00193 AFIX 43 H4 2 0.947540 -0.064285 0.799622 11.00000 -1.20000 AFIX 65 C5 1 1.068167 0.157731 0.780937 11.00000 0.02137 0.02188 = 0.02047 0.00660 -0.00111 -0.00164 C6 1 1.068031 0.338158 0.744078 11.00000 0.02185 0.01808 = 0.02042 0.00369 0.00078 -0.00711 C7 1 0.947176 0.417288 0.701241 11.00000 0.02689 0.01939 = 0.02231 0.00850 -0.00075 0.00061 AFIX 43 H7 2 0.947085 0.538006 0.676579 11.00000 -1.20000 AFIX 0 C10 1 1.195971 0.073969 0.836760 11.00000 0.02449 0.03902 = 0.02544 0.01215 -0.00110 0.00606 AFIX 137 H10A 2 1.232830 0.168107 0.987274 11.00000 -1.50000 H10B 2 1.258882 0.063813 0.730561 11.00000 -1.50000 H10C 2 1.178393 -0.063880 0.828346 11.00000 -1.50000 AFIX 0 C11 1 1.196899 0.440807 0.741463 11.00000 0.02999 0.03309 = 0.03351 0.01100 0.00902 -0.00404 AFIX 137 H11A 2 1.243807 0.344830 0.618072 11.00000 -1.50000 H11B 2 1.250817 0.477157 0.881870 11.00000 -1.50000 H11C 2 1.179576 0.566949 0.722753 11.00000 -1.50000 AFIX 0 C12 1 0.489996 0.726862 0.826509 11.00000 0.04247 0.03926 = 0.04817 0.01391 0.00138 0.00612 AFIX 137 H12A 2 0.456808 0.589517 0.802358 11.00000 -1.50000 H12B 2 0.416138 0.809212 0.813467 11.00000 -1.50000 H12C 2 0.536638 0.797437 0.975196 11.00000 -1.50000 AFIX 0 HKLF 4 REM 35 in P-1 #2 REM R1 = 0.0525 for 312 Fo > 4sig(Fo) and 0.0896 for all 449 data REM 110 parameters refined using 186 restraints END WGHT 0.0908 0.2092 REM Highest difference peak 0.163, deepest hole -0.147, 1-sigma level 0.044 Q1 1 0.5771 0.6841 1.1364 11.00000 0.05 0.16 Q2 1 0.6498 0.5911 0.5646 11.00000 0.05 0.15 Q3 1 0.5596 0.6206 0.9710 11.00000 0.05 0.15 Q4 1 1.0255 -0.1091 0.6730 11.00000 0.05 0.14 Q5 1 1.3441 -0.1079 0.6470 11.00000 0.05 0.13 ; _shelx_res_checksum 63642 _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 0.5777(12) 0.7042(8) 0.6647(10) 0.039(4) Uani 1 1 d . U H1A H 0.6150 0.8192 0.6970 0.059 Uiso 1 1 calc GR . N1 N 0.6973(13) 0.3541(10) 0.6565(10) 0.028(4) Uani 1 1 d . U H1 H 0.6688 0.4558 0.6272 0.034 Uiso 1 1 calc R . N3 N 0.6946(13) 0.0653(9) 0.7172(10) 0.026(3) Uani 1 1 d . U C2 C 0.6209(17) 0.2032(12) 0.6721(13) 0.033(4) Uani 1 1 d . U H2 H 0.5276 0.1962 0.6536 0.039 Uiso 1 1 calc R . C8 C 0.8265(7) 0.3160(7) 0.6953(7) 0.025(3) Uani 1 1 d . U C9 C 0.8266(7) 0.1356(7) 0.7321(7) 0.024(3) Uani 1 1 d G U C4 C 0.9474(8) 0.0564(6) 0.7750(7) 0.020(3) Uani 1 1 d G U H4 H 0.9475 -0.0643 0.7996 0.023 Uiso 1 1 calc R . C5 C 1.0682(7) 0.1577(7) 0.7809(7) 0.022(3) Uani 1 1 d G U C6 C 1.0680(7) 0.3382(7) 0.7441(8) 0.022(3) Uani 1 1 d G U C7 C 0.9472(8) 0.4173(6) 0.7012(7) 0.023(3) Uani 1 1 d G U H7 H 0.9471 0.5380 0.6766 0.028 Uiso 1 1 calc R . C10 C 1.1960(14) 0.0740(11) 0.8368(12) 0.031(5) Uani 1 1 d . U H10A H 1.2328 0.1681 0.9873 0.046 Uiso 1 1 calc GR . H10B H 1.2589 0.0638 0.7306 0.046 Uiso 1 1 calc GR . H10C H 1.1784 -0.0639 0.8283 0.046 Uiso 1 1 calc GR . C11 C 1.1969(18) 0.4408(12) 0.7415(14) 0.033(4) Uani 1 1 d . U H11A H 1.2438 0.3448 0.6181 0.050 Uiso 1 1 calc GR . H11B H 1.2508 0.4772 0.8819 0.050 Uiso 1 1 calc GR . H11C H 1.1796 0.5669 0.7228 0.050 Uiso 1 1 calc GR . C12 C 0.4900(19) 0.7269(14) 0.8265(15) 0.045(5) Uani 1 1 d . U H12A H 0.4568 0.5895 0.8024 0.068 Uiso 1 1 calc GR . H12B H 0.4161 0.8092 0.8135 0.068 Uiso 1 1 calc GR . H12C H 0.5366 0.7974 0.9752 0.068 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 0.044(9) 0.029(3) 0.042(3) 0.013(2) 0.001(5) 0.010(4) N1 0.028(8) 0.027(3) 0.033(4) 0.017(3) -0.002(5) 0.004(4) N3 0.028(7) 0.027(3) 0.028(3) 0.015(2) 0.003(5) 0.005(4) C2 0.029(8) 0.028(4) 0.038(4) 0.013(3) -0.004(5) -0.001(5) C8 0.020(6) 0.020(3) 0.026(4) 0.005(3) -0.009(5) 0.002(4) C9 0.023(7) 0.022(3) 0.023(4) 0.008(2) 0.001(5) 0.000(5) C4 0.025(7) 0.017(3) 0.022(4) 0.013(2) 0.002(5) 0.002(4) C5 0.021(7) 0.022(4) 0.020(4) 0.007(2) -0.001(5) -0.002(5) C6 0.022(7) 0.018(4) 0.020(4) 0.004(3) 0.001(5) -0.007(5) C7 0.027(7) 0.019(4) 0.022(4) 0.008(3) -0.001(5) 0.001(4) C10 0.024(9) 0.039(4) 0.025(4) 0.012(3) -0.001(5) 0.006(5) C11 0.030(8) 0.033(4) 0.034(5) 0.011(3) 0.009(6) -0.004(5) C12 0.042(10) 0.039(5) 0.048(5) 0.014(4) 0.001(6) 0.006(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 C2 N1 H1 126.3 C8 N1 H1 126.3 C8 N1 C2 107.3(6) C2 N3 C9 104.5(11) N1 C2 H2 123.8 N3 C2 N1 112.4(14) N3 C2 H2 123.8 N1 C8 C9 107.0(6) N1 C8 C7 133.0(6) C9 C8 C7 120.0 C8 C9 N3 108.8(4) C4 C9 N3 131.2(4) C4 C9 C8 120.0 C9 C4 H4 120.0 C9 C4 C5 120.0 C5 C4 H4 120.0 C4 C5 C10 118.7(7) C6 C5 C4 120.0 C6 C5 C10 121.3(7) C5 C6 C11 119.9(4) C7 C6 C5 120.0 C7 C6 C11 120.1(4) 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 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 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 H1A 0.8200 O1 C12 1.39(3) N1 H1 0.8600 N1 C2 1.35(2) N1 C8 1.346(11) N3 C2 1.336(7) N3 C9 1.390(16) 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 1.493(8) C6 C7 1.3900 C6 C11 1.48(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 C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 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 -0.6(4) N1 C8 C9 C4 179.4(4) N1 C8 C7 C6 -179.2(5) N3 C9 C4 C5 180.0(6) C2 N1 C8 C9 0.8(6) C2 N1 C8 C7 -179.9(5) C2 N3 C9 C8 0.1(6) C2 N3 C9 C4 -179.8(4) C8 N1 C2 N3 -0.7(9) C8 C9 C4 C5 0.0 C9 N3 C2 N1 0.4(8) C9 C8 C7 C6 0.0 C9 C4 C5 C6 0.0 C9 C4 C5 C10 177.5(4) C4 C5 C6 C7 0.0 C4 C5 C6 C11 -177.6(6) C5 C6 C7 C8 0.0 C7 C8 C9 N3 -180.0(4) C7 C8 C9 C4 0.0 C10 C5 C6 C7 -177.5(4) C10 C5 C6 C11 5.0(6) C11 C6 C7 C8 177.6(6)