#------------------------------------------------------------------------------ #$Date: 2016-05-06 03:44:14 +0300 (Fri, 06 May 2016) $ #$Revision: 182633 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224786.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_7224786 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 'C2 H6 O, C9 H10 N2' _chemical_formula_sum 'C11 H16 N2 O' _chemical_formula_weight 192.26 _chemical_name_common '5,6-dimethylbenzimidazole ethanol solvate' _chemical_name_systematic '5,6-dimethylbenzimidazole ethanol 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 67.00(2) _cell_angle_beta 81.82(2) _cell_angle_gamma 71.19(2) _cell_formula_units_Z 2 _cell_length_a 7.081(2) _cell_length_b 8.559(2) _cell_length_c 9.604(3) _cell_measurement_reflns_used 1034 _cell_measurement_temperature 296 _cell_measurement_theta_max 29.3339 _cell_measurement_theta_min 2.6988 _cell_volume 507.1(3) _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 8.1929 _diffrn_measured_fraction_theta_full 0.277 _diffrn_measured_fraction_theta_max 0.221 _diffrn_measurement_details ; 1 phi -35.00 19.75 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 73 2 phi 140.00 200.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 80 3 phi 160.00 217.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 76 4 phi -20.00 34.75 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 73 5 omega -24.00 24.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 -12.9000 64 6 omega -24.00 24.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 167.1000 64 7 omega -50.00 10.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 167.1000 80 8 omega -50.00 10.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 -12.9000 80 9 omega -64.00 -8.50 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 -28.9000 74 10 omega -64.00 -8.50 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 151.1000 74 11 omega -19.00 8.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 151.1000 36 12 omega -19.00 8.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 -28.9000 36 13 omega -43.00 -21.25 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 -56.9000 29 14 omega -43.00 -21.25 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 123.1000 29 15 omega -90.00 -36.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 123.1000 72 16 omega -90.00 -36.00 0.7500 29.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 -56.9000 72 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w and \p scans' _diffrn_orient_matrix_UB_11 -0.0804246000 _diffrn_orient_matrix_UB_12 0.0353132000 _diffrn_orient_matrix_UB_13 -0.0504249000 _diffrn_orient_matrix_UB_21 0.0410375000 _diffrn_orient_matrix_UB_22 -0.0707744000 _diffrn_orient_matrix_UB_23 -0.0266180000 _diffrn_orient_matrix_UB_31 -0.0552375000 _diffrn_orient_matrix_UB_32 -0.0511066000 _diffrn_orient_matrix_UB_33 0.0564834000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1837 _diffrn_reflns_av_unetI/netI 0.0938 _diffrn_reflns_Laue_measured_fraction_full 0.277 _diffrn_reflns_Laue_measured_fraction_max 0.221 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3791 _diffrn_reflns_point_group_measured_fraction_full 0.277 _diffrn_reflns_point_group_measured_fraction_max 0.221 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.400 _diffrn_reflns_theta_min 2.704 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.05506 _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 1.259 _exptl_crystal_description plate _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.177 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef 0.27(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 620 _refine_ls_number_restraints 197 _refine_ls_restrained_S_all 0.951 _refine_ls_R_factor_all 0.1535 _refine_ls_R_factor_gt 0.0905 _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^)+(0.1530P)^2^+0.2770P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2311 _refine_ls_wR_factor_ref 0.3014 _reflns_Friedel_coverage 0.000 _reflns_number_gt 316 _reflns_number_total 620 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00419a2.cif _cod_data_source_block dMBzIm_EtOH_0_84GPa _cod_depositor_comments 'Adding full bibliography for 7224786--7224795.cif.' _cod_database_code 7224786 _chemical_oxdiff_formula C9H10N2 _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 26.62 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,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 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 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 N1 \\sim N3 \\sim C2 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim H7 \\sim C8 \\sim C9 \\sim C10 \\sim H10A \\sim C11: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(O1) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C11) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2 4.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B) 4.b Aromatic/amide H refined with riding coordinates: N3(H3), C2(H2), C4(H4), C7(H7) 4.c Fitted hexagon refined as free rotating group: C9(C4,C5,C6,C7,C8) 4.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C) 4.e Idealised tetrahedral OH refined as rotating group: O1(H1) ; _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 7.081276 8.558682 9.603689 67.0001 81.8209 71.1916 ZERR 2 0.002006 0.002 0.002515 0.0234 0.0225 0.0232 LATT 1 SFAC C H N O UNIT 22 32 4 2 DELU N1 N3 C2 C4 > C8 C9 C10 C11 DELU N1 N3 C2 C4 > C8 C9 C10 C11 SIMU 0.04 0.08 1.7 N1 N3 C2 C4 > C7 H7 C8 C9 C10 H10a C11 ISOR 0.01 0.02 O1 C12 C13 ISOR 0.01 0.02 C10 C9 C4 C8 N3 C5 C7 N1 C2 C6 C11 ISOR C11 C9 C4 C8 N3 C5 C7 N1 C2 C6 C10 L.S. 44 PLAN 5 BOND $h fmap 2 acta MORE -1 CONF OMIT -1 4 5 OMIT 0 2 4 OMIT -2 -2 4 OMIT -3 2 9 OMIT -2 -5 3 OMIT 3 10 0 OMIT -1 -2 3 OMIT -3 -4 5 OMIT -4 2 7 OMIT 0 1 1 OMIT 3 5 2 REM REM REM WGHT 0.153000 0.277000 EXTI 0.270243 FVAR 3.07881 O1 4 0.040805 0.254718 0.156720 11.00000 0.09024 0.08455 = 0.09754 -0.05573 0.02622 -0.03895 AFIX 147 H1 2 -0.076322 0.296696 0.177214 11.00000 -1.50000 AFIX 0 C12 1 0.055439 0.248643 0.007937 11.00000 0.08999 0.06930 = 0.06041 -0.02961 -0.00115 -0.01439 AFIX 23 H12A 2 0.082489 0.355314 -0.065848 11.00000 -1.20000 H12B 2 -0.070315 0.244124 -0.016853 11.00000 -1.20000 AFIX 0 C13 1 0.216472 0.091294 0.001147 11.00000 0.11402 0.08513 = 0.09025 -0.05244 0.01339 -0.02233 AFIX 137 H13A 2 0.342496 0.101570 0.016082 11.00000 -1.50000 H13B 2 0.217368 0.083479 -0.095991 11.00000 -1.50000 H13C 2 0.194362 -0.013583 0.078933 11.00000 -1.50000 AFIX 0 N1 3 0.645679 0.398953 0.187471 11.00000 0.05907 0.05806 = 0.06844 -0.02708 -0.00085 -0.01859 N3 3 0.345482 0.358407 0.208616 11.00000 0.06521 0.05735 = 0.06599 -0.03050 -0.00142 -0.02219 AFIX 43 H3 2 0.254195 0.315081 0.202784 11.00000 -1.20000 AFIX 0 C2 1 0.535872 0.315573 0.162706 11.00000 0.06459 0.06625 = 0.07793 -0.03706 -0.00007 -0.02048 AFIX 43 H2 2 0.586627 0.232663 0.116574 11.00000 -1.20000 AFIX 66 C9 1 0.325835 0.486171 0.267130 11.00000 0.05685 0.04516 = 0.05600 -0.01761 -0.00449 -0.01801 C4 1 0.165666 0.583760 0.329667 11.00000 0.05881 0.05384 = 0.05082 -0.02225 -0.00328 -0.02299 AFIX 43 H4 2 0.040825 0.566438 0.338055 11.00000 -1.20000 AFIX 65 C5 1 0.192085 0.707239 0.379668 11.00000 0.05517 0.05143 = 0.04990 -0.02053 0.00530 -0.02163 C6 1 0.378674 0.733130 0.367133 11.00000 0.06261 0.05275 = 0.06262 -0.02402 0.00013 -0.02543 C7 1 0.538845 0.635542 0.304596 11.00000 0.05521 0.05626 = 0.05896 -0.01710 -0.00095 -0.02938 AFIX 43 H7 2 0.663686 0.652866 0.296209 11.00000 -1.20000 AFIX 65 C8 1 0.512429 0.512062 0.254594 11.00000 0.05668 0.04288 = 0.04884 -0.00930 -0.00592 -0.01639 AFIX 0 C10 1 0.021916 0.811055 0.447163 11.00000 0.05895 0.06457 = 0.06075 -0.03544 -0.00554 -0.01819 AFIX 137 H10A 2 -0.010815 0.934193 0.382601 11.00000 -1.50000 H10B 2 0.057877 0.797424 0.544834 11.00000 -1.50000 H10C 2 -0.091476 0.768755 0.457748 11.00000 -1.50000 AFIX 0 C11 1 0.407662 0.870342 0.419494 11.00000 0.06999 0.03785 = 0.04914 -0.00397 -0.03168 -0.00944 AFIX 137 H11A 2 0.335563 0.987173 0.354887 11.00000 -1.50000 H11B 2 0.547032 0.860938 0.414897 11.00000 -1.50000 H11C 2 0.358659 0.849388 0.521695 11.00000 -1.50000 AFIX 0 HKLF 4 REM 35 in P-1 #2 REM R1 = 0.0905 for 316 Fo > 4sig(Fo) and 0.1535 for all 620 data REM 120 parameters refined using 197 restraints END WGHT 0.1516 0.2773 REM Highest difference peak 0.177, deepest hole -0.139, 1-sigma level 0.041 Q1 1 -0.0031 0.1533 0.1158 11.00000 0.05 0.18 Q2 1 0.3638 0.5139 0.2525 11.00000 0.05 0.17 Q3 1 0.3222 0.5442 0.2255 11.00000 0.05 0.17 Q4 1 0.3237 0.4825 0.4386 11.00000 0.05 0.17 Q5 1 0.3569 0.4614 0.4648 11.00000 0.05 0.16 ; _shelx_res_checksum 24849 _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 0.0408(18) 0.2547(10) 0.1567(12) 0.083(9) Uani 1 1 d . U H1 H -0.0763 0.2967 0.1772 0.125 Uiso 1 1 calc GR . C12 C 0.055(3) 0.2486(15) 0.008(2) 0.074(6) Uani 1 1 d . U H12A H 0.0825 0.3553 -0.0658 0.088 Uiso 1 1 calc R . H12B H -0.0703 0.2441 -0.0169 0.088 Uiso 1 1 calc R . C13 C 0.216(3) 0.0913(16) 0.001(2) 0.093(10) Uani 1 1 d . U H13A H 0.3425 0.1016 0.0161 0.140 Uiso 1 1 calc GR . H13B H 0.2174 0.0835 -0.0960 0.140 Uiso 1 1 calc GR . H13C H 0.1944 -0.0136 0.0789 0.140 Uiso 1 1 calc GR . N1 N 0.646(2) 0.3990(12) 0.1875(15) 0.060(5) Uani 1 1 d . U N3 N 0.345(2) 0.3584(12) 0.2086(15) 0.059(4) Uani 1 1 d . U H3 H 0.2542 0.3151 0.2028 0.071 Uiso 1 1 calc R . C2 C 0.536(3) 0.3156(17) 0.163(2) 0.066(5) Uani 1 1 d . U H2 H 0.5866 0.2327 0.1166 0.079 Uiso 1 1 calc R . C9 C 0.3258(14) 0.4862(9) 0.2671(10) 0.052(4) Uani 1 1 d . U C4 C 0.1657(13) 0.5838(8) 0.3297(10) 0.052(5) Uani 1 1 d G U H4 H 0.0408 0.5664 0.3381 0.062 Uiso 1 1 calc R . C5 C 0.1921(14) 0.7072(8) 0.3797(11) 0.051(4) Uani 1 1 d G U C6 C 0.3787(14) 0.7331(9) 0.3671(10) 0.056(4) Uani 1 1 d G U C7 C 0.5388(13) 0.6355(8) 0.3046(10) 0.055(4) Uani 1 1 d G U H7 H 0.6637 0.6529 0.2962 0.066 Uiso 1 1 calc R U C8 C 0.5124(13) 0.5121(8) 0.2546(11) 0.051(4) Uani 1 1 d G U C10 C 0.022(3) 0.8111(15) 0.4472(18) 0.057(8) Uani 1 1 d . U H10A H -0.0108 0.9342 0.3826 0.085 Uiso 1 1 calc GR U H10B H 0.0579 0.7974 0.5448 0.085 Uiso 1 1 calc GR . H10C H -0.0915 0.7688 0.4577 0.085 Uiso 1 1 calc GR . C11 C 0.408(3) 0.8703(14) 0.4195(18) 0.055(8) Uani 1 1 d . U H11A H 0.3356 0.9872 0.3549 0.082 Uiso 1 1 calc GR . H11B H 0.5470 0.8609 0.4149 0.082 Uiso 1 1 calc GR . H11C H 0.3587 0.8494 0.5217 0.082 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 0.090(16) 0.085(6) 0.098(13) -0.056(8) 0.026(13) -0.039(9) C12 0.090(11) 0.069(6) 0.060(10) -0.030(6) -0.001(9) -0.014(7) C13 0.11(2) 0.085(8) 0.090(16) -0.052(10) 0.013(16) -0.022(11) N1 0.059(8) 0.058(5) 0.068(8) -0.027(5) -0.001(7) -0.019(5) N3 0.065(8) 0.057(4) 0.066(8) -0.030(5) -0.001(7) -0.022(5) C2 0.065(9) 0.066(5) 0.078(9) -0.037(6) 0.000(7) -0.020(6) C9 0.057(8) 0.045(5) 0.056(8) -0.018(5) -0.004(7) -0.018(5) C4 0.059(9) 0.054(5) 0.051(9) -0.022(5) -0.003(7) -0.023(6) C5 0.055(8) 0.051(5) 0.050(8) -0.021(5) 0.005(7) -0.022(5) C6 0.063(8) 0.053(5) 0.063(8) -0.024(5) 0.000(7) -0.025(6) C7 0.055(8) 0.056(5) 0.059(8) -0.017(5) -0.001(7) -0.029(5) C8 0.057(8) 0.043(5) 0.049(8) -0.009(5) -0.006(7) -0.016(5) C10 0.059(14) 0.065(7) 0.061(14) -0.035(8) -0.006(13) -0.018(8) C11 0.070(15) 0.038(6) 0.049(13) -0.004(8) -0.032(12) -0.009(9) 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 H1 109.5 O1 C12 H12A 109.6 O1 C12 H12B 109.6 O1 C12 C13 110.4(16) H12A C12 H12B 108.1 C13 C12 H12A 109.6 C13 C12 H12B 109.6 C12 C13 H13A 109.5 C12 C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C2 N1 C8 104.0(10) C2 N3 H3 127.2 C2 N3 C9 105.7(10) C9 N3 H3 127.2 N1 C2 N3 115.0(8) N1 C2 H2 122.5 N3 C2 H2 122.5 N3 C9 C4 133.2(7) N3 C9 C8 106.8(7) C4 C9 C8 120.0 C9 C4 H4 120.0 C5 C4 C9 120.0 C5 C4 H4 120.0 C4 C5 C10 120.2(7) C6 C5 C4 120.0 C6 C5 C10 119.8(7) C5 C6 C11 120.2(7) C7 C6 C5 120.0 C7 C6 C11 119.8(7) C6 C7 H7 120.0 C6 C7 C8 120.0 C8 C7 H7 120.0 C9 C8 N1 108.5(7) C7 C8 N1 131.5(7) C7 C8 C9 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 H1 0.8200 O1 C12 1.438(17) C12 H12A 0.9700 C12 H12B 0.9700 C12 C13 1.475(19) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 N1 C2 1.31(2) N1 C8 1.403(7) N3 H3 0.8600 N3 C2 1.336(18) N3 C9 1.375(8) C2 H2 0.9300 C9 C4 1.3900 C9 C8 1.3900 C4 H4 0.9300 C4 C5 1.3900 C5 C6 1.3900 C5 C10 1.483(9) C6 C7 1.3900 C6 C11 1.523(12) C7 H7 0.9300 C7 C8 1.3900 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 N3 C9 C4 C5 -179.7(12) N3 C9 C8 N1 0.1(10) N3 C9 C8 C7 179.8(9) C2 N1 C8 C9 0.6(12) C2 N1 C8 C7 -178.9(11) C2 N3 C9 C4 178.9(11) C2 N3 C9 C8 -0.8(13) C9 N3 C2 N1 1.3(19) C9 C4 C5 C6 0.0 C9 C4 C5 C10 -179.7(10) C4 C9 C8 N1 -179.6(9) C4 C9 C8 C7 0.0 C4 C5 C6 C7 0.0 C4 C5 C6 C11 179.0(10) C5 C6 C7 C8 0.0 C6 C7 C8 N1 179.5(11) C6 C7 C8 C9 0.0 C8 N1 C2 N3 -1.2(18) C8 C9 C4 C5 0.0 C10 C5 C6 C7 179.7(10) C10 C5 C6 C11 -1.3(12) C11 C6 C7 C8 -179.0(10)