#------------------------------------------------------------------------------ #$Date: 2016-04-05 06:25:52 +0300 (Tue, 05 Apr 2016) $ #$Revision: 181491 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224788.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_7224788 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 '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 66.49(2) _cell_angle_beta 81.840(9) _cell_angle_gamma 71.705(18) _cell_formula_units_Z 2 _cell_length_a 7.0048(7) _cell_length_b 8.453(3) _cell_length_c 9.3834(12) _cell_measurement_reflns_used 887 _cell_measurement_temperature 296 _cell_measurement_theta_max 26.4730 _cell_measurement_theta_min 3.9010 _cell_volume 483.6(2) _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 16.2413 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.292 _diffrn_measured_fraction_theta_max 0.268 _diffrn_measurement_details ; 1 phi -35.00 19.75 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 73 2 phi 140.00 200.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 -30.0000 0.0000 - 80 3 phi 160.00 217.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 76 4 phi -20.00 34.75 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames 0.0000 30.0000 0.0000 - 73 5 omega -24.00 24.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 -12.9000 64 6 omega -24.00 24.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 39.4600 167.1000 64 7 omega -50.00 10.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 167.1000 80 8 omega -50.00 10.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 39.4600 -12.9000 80 9 omega -64.00 -8.50 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 -28.9000 74 10 omega -64.00 -8.50 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 81.4000 151.1000 74 11 omega -19.00 8.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 151.1000 36 12 omega -19.00 8.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 81.4000 -28.9000 36 13 omega -43.00 -21.25 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 -56.9000 29 14 omega -43.00 -21.25 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - 30.0000 134.6000 123.1000 29 15 omega -90.00 -36.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 123.1000 72 16 omega -90.00 -36.00 0.7500 34.0000 omega____ theta____ kappa____ phi______ frames - -30.0000 134.6000 -56.9000 72 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w and \p scans' _diffrn_orient_matrix_UB_11 0.0337514000 _diffrn_orient_matrix_UB_12 -0.0953209000 _diffrn_orient_matrix_UB_13 0.0329208000 _diffrn_orient_matrix_UB_21 0.1000157000 _diffrn_orient_matrix_UB_22 0.0036798000 _diffrn_orient_matrix_UB_23 -0.0011868000 _diffrn_orient_matrix_UB_31 -0.0153669000 _diffrn_orient_matrix_UB_32 0.0023362000 _diffrn_orient_matrix_UB_33 0.0755798000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_unetI/netI 0.0417 _diffrn_reflns_Laue_measured_fraction_full 0.292 _diffrn_reflns_Laue_measured_fraction_max 0.268 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2897 _diffrn_reflns_point_group_measured_fraction_full 0.292 _diffrn_reflns_point_group_measured_fraction_max 0.268 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.215 _diffrn_reflns_theta_min 3.909 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.01700 _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 1.320 _exptl_crystal_description plate _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.163 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.10(3) _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 1.155 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 132 _refine_ls_number_reflns 575 _refine_ls_number_restraints 84 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0571 _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^)+(0.0770P)^2^+0.2860P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1414 _refine_ls_wR_factor_ref 0.1608 _reflns_Friedel_coverage 0.000 _reflns_number_gt 430 _reflns_number_total 575 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00419a2.cif _cod_data_source_block dMBzIm_EtOH_1_50GPa _cod_database_code 7224788 _chemical_oxdiff_formula 'C11 H16 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 27.40 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.16 _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. Uiso/Uaniso restraints and constraints Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of 0.003 3.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B) 3.b Aromatic/amide H refined with riding coordinates: N1(H1), C2(H2), C4(H4), C7(H7) 3.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C) 3.d Idealised tetrahedral OH refined as rotating group: O1(H1A) ; _shelx_res_file ; wz-76.res created by SHELXL-2014/7 TITL WZ-76 in P-1 #2 REM reset to P-1 #2 CELL 0.71073 7.004787 8.452822 9.383448 66.4926 81.8399 71.7051 ZERR 2 0.000661 0.003054 0.001186 0.0222 0.0091 0.0179 LATT 1 SFAC C H N O UNIT 22 32 4 2 ISOR 0.006 0.003 H11c H10a H10c C10 H11b C9 H11a C5 C2 H2 H10b C11 H13b C7 = H13A H4 C8 H13C N3 C6 H1 C4 H1A O1 C12 H7 C13 N1 L.S. 44 PLAN 5 BOND MORE -1 CONF BOND $H fmap 2 acta 52 OMIT 4 4 2 OMIT 3 3 1 OMIT 5 5 4 OMIT -3 -1 1 OMIT 5 3 9 OMIT 3 4 4 OMIT 0 2 6 OMIT 7 5 3 OMIT 3 6 9 OMIT -3 -1 3 OMIT -3 -2 2 OMIT 0 3 4 OMIT -2 2 3 REM REM REM WGHT 0.077000 0.286000 EXTI 0.104136 FVAR 13.00130 O1 4 0.045479 0.247689 0.159279 11.00000 0.03440 0.03743 = 0.03698 -0.01479 -0.00012 -0.00920 AFIX 147 H1A 2 -0.065841 0.308865 0.175030 11.00000 -1.50000 AFIX 0 C12 1 0.056864 0.251358 0.006420 11.00000 0.04210 0.03865 = 0.04053 -0.02095 0.00005 -0.00701 AFIX 23 H12A 2 0.090176 0.359001 -0.066324 11.00000 -1.20000 H12B 2 -0.072030 0.253050 -0.021613 11.00000 -1.20000 AFIX 0 C13 1 0.213392 0.089769 -0.001003 11.00000 0.06014 0.05631 = 0.04940 -0.02318 0.00545 -0.00836 AFIX 137 H13A 2 0.179354 -0.016214 0.071036 11.00000 -1.50000 H13B 2 0.340822 0.089746 0.025515 11.00000 -1.50000 H13C 2 0.221617 0.090871 -0.104378 11.00000 -1.50000 AFIX 0 N1 3 0.349278 0.356900 0.209278 11.00000 0.03412 0.03917 = 0.03700 -0.01690 -0.00087 -0.01204 AFIX 43 H1 2 0.258271 0.311310 0.203310 11.00000 -1.20000 AFIX 0 N3 3 0.650546 0.398758 0.189538 11.00000 0.03244 0.03586 = 0.03998 -0.01619 0.00333 -0.00954 C2 1 0.540367 0.316168 0.162719 11.00000 0.04020 0.03470 = 0.04025 -0.02074 0.00413 -0.01215 AFIX 43 H2 2 0.591472 0.234140 0.114279 11.00000 -1.20000 AFIX 0 C4 1 0.541284 0.637856 0.305677 11.00000 0.02802 0.03595 = 0.02983 -0.00502 -0.00002 -0.01386 AFIX 43 H4 2 0.667424 0.655406 0.298596 11.00000 -1.20000 AFIX 0 C5 1 0.380787 0.737280 0.365137 11.00000 0.03593 0.03919 = 0.03352 -0.01549 -0.00194 -0.01355 C6 1 0.184777 0.713822 0.377878 11.00000 0.03380 0.03719 = 0.02449 -0.00729 0.00151 -0.01222 C7 1 0.162631 0.581910 0.331114 11.00000 0.02551 0.03094 = 0.02708 -0.00845 -0.00106 -0.00636 AFIX 43 H7 2 0.038625 0.559273 0.342131 11.00000 -1.20000 AFIX 0 C8 1 0.326259 0.485587 0.268485 11.00000 0.03020 0.02906 = 0.02433 -0.00740 -0.00068 -0.00766 C9 1 0.516556 0.510758 0.255827 11.00000 0.02670 0.02745 = 0.02383 -0.00674 0.00043 -0.00548 C10 1 0.403732 0.880613 0.412627 11.00000 0.04574 0.04702 = 0.04604 -0.01667 -0.00397 -0.01413 AFIX 137 H10A 2 0.313225 0.994383 0.354418 11.00000 -1.50000 H10B 2 0.539543 0.887984 0.392143 11.00000 -1.50000 H10C 2 0.373063 0.850890 0.521609 11.00000 -1.50000 AFIX 0 C11 1 0.009773 0.817734 0.441718 11.00000 0.03891 0.04003 = 0.04016 -0.01442 0.00196 -0.00994 AFIX 137 H11A 2 -0.023782 0.941908 0.372867 11.00000 -1.50000 H11B 2 0.041635 0.807381 0.541830 11.00000 -1.50000 H11C 2 -0.102624 0.771658 0.452078 11.00000 -1.50000 AFIX 0 HKLF 4 REM WZ-76 in P-1 #2 REM R1 = 0.0571 for 430 Fo > 4sig(Fo) and 0.0833 for all 575 data REM 132 parameters refined using 84 restraints END WGHT 0.0771 0.2861 REM Highest difference peak 0.163, deepest hole -0.167, 1-sigma level 0.034 Q1 1 0.2776 0.4234 0.4826 11.00000 0.05 0.16 Q2 1 0.2609 0.4697 0.4651 11.00000 0.05 0.16 Q3 1 0.1109 1.0261 0.2433 11.00000 0.05 0.13 Q4 1 0.1391 0.9696 0.2625 11.00000 0.05 0.13 Q5 1 0.0849 0.0747 0.2202 11.00000 0.05 0.12 ; _shelx_res_checksum 15141 _shelx_shelxl_version_number 2014/7 _olex2_date_sample_data_collection 1404125105.96 _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 0.0455(6) 0.2477(13) 0.1593(5) 0.0363(16) Uani 1 1 d . U H1A H -0.0658 0.3089 0.1750 0.054 Uiso 1 1 calc GR U C12 C 0.0569(9) 0.251(2) 0.0064(9) 0.040(3) Uani 1 1 d . U H12A H 0.0902 0.3590 -0.0663 0.048 Uiso 1 1 calc R . H12B H -0.0720 0.2530 -0.0216 0.048 Uiso 1 1 calc R . C13 C 0.2134(11) 0.090(2) -0.0010(10) 0.057(2) Uani 1 1 d . U H13A H 0.1794 -0.0162 0.0710 0.085 Uiso 1 1 calc GR U H13B H 0.3408 0.0897 0.0255 0.085 Uiso 1 1 calc GR U H13C H 0.2216 0.0909 -0.1044 0.085 Uiso 1 1 calc GR U N1 N 0.3493(7) 0.3569(15) 0.2093(7) 0.035(3) Uani 1 1 d . U H1 H 0.2583 0.3113 0.2033 0.043 Uiso 1 1 calc R U N3 N 0.6505(6) 0.3988(15) 0.1895(7) 0.036(3) Uani 1 1 d . U C2 C 0.5404(8) 0.3162(19) 0.1627(8) 0.036(3) Uani 1 1 d . U H2 H 0.5915 0.2341 0.1143 0.044 Uiso 1 1 calc R U C4 C 0.5413(8) 0.6379(19) 0.3057(8) 0.033(3) Uani 1 1 d . U H4 H 0.6674 0.6554 0.2986 0.039 Uiso 1 1 calc R U C5 C 0.3808(8) 0.737(2) 0.3651(8) 0.035(3) Uani 1 1 d . U C6 C 0.1848(8) 0.7138(19) 0.3779(8) 0.033(3) Uani 1 1 d . U C7 C 0.1626(8) 0.5819(18) 0.3311(7) 0.029(3) Uani 1 1 d . U H7 H 0.0386 0.5593 0.3421 0.035 Uiso 1 1 calc R U C8 C 0.3263(8) 0.4856(18) 0.2685(7) 0.029(3) Uani 1 1 d . U C9 C 0.5166(8) 0.5108(18) 0.2558(7) 0.028(3) Uani 1 1 d . U C10 C 0.4037(9) 0.881(2) 0.4126(9) 0.0460(19) Uani 1 1 d . U H10A H 0.3132 0.9944 0.3544 0.069 Uiso 1 1 calc GR U H10B H 0.5395 0.8880 0.3921 0.069 Uiso 1 1 calc GR U H10C H 0.3731 0.8509 0.5216 0.069 Uiso 1 1 calc GR U C11 C 0.0098(9) 0.818(2) 0.4417(9) 0.0405(19) Uani 1 1 d . U H11A H -0.0238 0.9419 0.3729 0.061 Uiso 1 1 calc GR U H11B H 0.0416 0.8074 0.5418 0.061 Uiso 1 1 calc GR U H11C H -0.1026 0.7717 0.4521 0.061 Uiso 1 1 calc GR U 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 0.0344(17) 0.037(4) 0.037(2) -0.015(2) -0.0001(13) -0.009(2) C12 0.042(3) 0.039(8) 0.041(3) -0.021(5) 0.000(2) -0.007(4) C13 0.060(3) 0.056(4) 0.049(3) -0.023(3) 0.005(2) -0.008(3) N1 0.034(2) 0.039(8) 0.037(3) -0.017(4) -0.0009(19) -0.012(4) N3 0.032(2) 0.036(8) 0.040(3) -0.016(4) 0.003(2) -0.010(4) C2 0.040(3) 0.035(8) 0.040(3) -0.021(4) 0.004(2) -0.012(4) C4 0.028(3) 0.036(8) 0.030(3) -0.005(4) 0.000(2) -0.014(4) C5 0.036(3) 0.039(8) 0.034(3) -0.015(4) -0.002(2) -0.014(4) C6 0.034(3) 0.037(8) 0.024(3) -0.007(4) 0.002(2) -0.012(4) C7 0.026(2) 0.031(8) 0.027(3) -0.008(4) -0.001(2) -0.006(4) C8 0.030(3) 0.029(8) 0.024(3) -0.007(4) -0.001(2) -0.008(4) C9 0.027(2) 0.027(8) 0.024(3) -0.007(4) 0.000(2) -0.005(4) C10 0.046(2) 0.047(4) 0.046(3) -0.017(3) -0.0040(18) -0.014(3) C11 0.039(2) 0.040(4) 0.040(2) -0.014(3) 0.0020(17) -0.010(3) 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 109.9 O1 C12 H12B 109.9 O1 C12 C13 108.9(10) H12A C12 H12B 108.3 C13 C12 H12A 109.9 C13 C12 H12B 109.9 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 H1 126.9 C2 N1 C8 106.3(6) C8 N1 H1 126.9 C2 N3 C9 103.5(5) N1 C2 H2 122.3 N3 C2 N1 115.3(8) N3 C2 H2 122.3 C5 C4 H4 119.8 C5 C4 C9 120.5(5) C9 C4 H4 119.8 C4 C5 C6 121.3(9) C4 C5 C10 120.9(5) C6 C5 C10 117.7(7) C5 C6 C11 122.6(8) C7 C6 C5 117.7(7) C7 C6 C11 119.6(5) C6 C7 H7 120.1 C8 C7 C6 119.9(5) C8 C7 H7 120.1 N1 C8 C7 133.1(5) N1 C8 C9 105.2(6) C7 C8 C9 121.7(8) N3 C9 C4 131.5(4) N3 C9 C8 109.6(7) C4 C9 C8 118.9(7) 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 1.414(5) C12 H12A 0.9700 C12 H12B 0.9700 C12 C13 1.479(18) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 N1 H1 0.8600 N1 C2 1.329(6) N1 C8 1.365(12) N3 C2 1.296(9) N3 C9 1.382(11) C2 H2 0.9300 C4 H4 0.9300 C4 C5 1.373(11) C4 C9 1.394(12) C5 C6 1.430(6) C5 C10 1.505(14) C6 C7 1.406(13) C6 C11 1.473(11) C7 H7 0.9300 C7 C8 1.388(10) C8 C9 1.396(6) 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 0.2(11) N1 C8 C9 C4 179.2(8) C2 N1 C8 C7 178.6(11) C2 N1 C8 C9 -1.5(11) C2 N3 C9 C4 -177.6(10) C2 N3 C9 C8 1.2(10) C4 C5 C6 C7 1.6(15) C4 C5 C6 C11 179.7(10) C5 C4 C9 N3 178.3(10) C5 C4 C9 C8 -0.5(14) C5 C6 C7 C8 -2.9(14) C6 C7 C8 N1 -177.5(10) C6 C7 C8 C9 2.6(15) C7 C8 C9 N3 -179.9(9) C7 C8 C9 C4 -0.9(14) C8 N1 C2 N3 2.5(12) C9 N3 C2 N1 -2.3(11) C9 C4 C5 C6 0.0(16) C9 C4 C5 C10 -177.2(9) C10 C5 C6 C7 179.0(8) C10 C5 C6 C11 -2.9(15) C11 C6 C7 C8 178.9(9)