#------------------------------------------------------------------------------ #$Date: 2016-04-05 06:25:52 +0300 (Tue, 05 Apr 2016) $ #$Revision: 181491 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224787.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_7224787 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 66.75(2) _cell_angle_beta 81.96(2) _cell_angle_gamma 71.38(2) _cell_formula_units_Z 2 _cell_length_a 7.0242(16) _cell_length_b 8.496(2) _cell_length_c 9.475(2) _cell_measurement_reflns_used 1048 _cell_measurement_temperature 296 _cell_measurement_theta_max 29.1569 _cell_measurement_theta_min 2.7854 _cell_volume 492.3(2) _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_measured_fraction_theta_full 0.272 _diffrn_measured_fraction_theta_max 0.241 _diffrn_measurement_device_type 'KUMA CCD' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1240 _diffrn_reflns_av_unetI/netI 0.0751 _diffrn_reflns_Laue_measured_fraction_full 0.272 _diffrn_reflns_Laue_measured_fraction_max 0.241 _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 3470 _diffrn_reflns_point_group_measured_fraction_full 0.272 _diffrn_reflns_point_group_measured_fraction_max 0.241 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 28.172 _diffrn_reflns_theta_min 3.459 _exptl_absorpt_coefficient_mu 0.085 _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.297 _exptl_crystal_description cube _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 0.210 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 582 _refine_ls_number_restraints 168 _refine_ls_restrained_S_all 0.992 _refine_ls_R_factor_all 0.1410 _refine_ls_R_factor_gt 0.0957 _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^)+(0.1880P)^2^+0.2360P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2530 _refine_ls_wR_factor_ref 0.3100 _reflns_Friedel_coverage 0.000 _reflns_number_gt 344 _reflns_number_total 582 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00419a2.cif _cod_data_source_block dMBzIm_EtOH_1_20GPa _cod_database_code 7224787 _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. ; _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 All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 All non-hydrogen atoms restrained to be isotropic: with sigma of 0.02 and sigma for terminal atoms of 0.001 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 Fitted hexagon refined as free rotating group: C5(C4,C9,C8,C7,C6) 3.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C) 3.e Idealised tetrahedral OH refined as rotating group: O1(H1A) ; _shelx_res_file ; 36b.res created by SHELXL-2014/7 TITL 36b in P-1 REM P-1 (#2 in standard setting) CELL 0.71073 7.024183 8.495998 9.475274 66.7451 81.962 71.3793 ZERR 2 0.001608 0.002098 0.002353 0.0236 0.0198 0.0218 LATT 1 SFAC C H N O UNIT 22 32 4 2 EQIV $1 -1+X,+Y,+Z SIMU 0.04 0.08 1.7 ISOR 0.02 0.001 L.S. 44 PLAN 10 TEMP 22.85 HTAB O1 N3_$1 HTAB N1 O1 BOND $H MORE -1 CONF fmap 2 acta 52 OMIT 0 2 4 OMIT -1 4 5 OMIT 1 4 1 OMIT -1 2 3 OMIT -2 5 4 OMIT -3 -4 5 OMIT -2 4 7 OMIT -3 -2 6 OMIT -1 1 3 OMIT 3 3 0 OMIT -5 0 4 OMIT -1 4 4 OMIT -3 3 6 OMIT -3 2 4 OMIT -3 5 6 OMIT -2 -2 4 OMIT -2 -5 3 OMIT -1 -4 2 OMIT -1 -2 3 OMIT -2 -1 4 OMIT 2 8 6 OMIT -4 -3 2 OMIT -2 3 8 OMIT 2 3 0 OMIT 3 6 2 OMIT -2 3 4 REM REM REM WGHT 0.188000 0.236000 FVAR 8.99658 O1 4 0.045865 0.249675 0.160622 11.00000 0.05390 0.05524 = 0.05302 -0.02220 0.00027 -0.01383 AFIX 147 H1A 2 -0.072330 0.265088 0.188406 11.00000 -1.50000 AFIX 0 C12 1 0.066307 0.243705 0.012379 11.00000 0.09497 0.07207 = 0.07594 -0.04567 0.02845 -0.03441 AFIX 23 H12A 2 0.098925 0.350038 -0.060516 11.00000 -1.20000 H12B 2 -0.060899 0.244308 -0.016934 11.00000 -1.20000 AFIX 0 C13 1 0.222050 0.085349 0.004582 11.00000 0.06744 0.06737 = 0.06681 -0.02582 -0.00085 -0.01871 AFIX 137 H13A 2 0.193864 -0.020192 0.079983 11.00000 -1.50000 H13B 2 0.350251 0.089536 0.024583 11.00000 -1.50000 H13C 2 0.224521 0.082498 -0.095950 11.00000 -1.50000 AFIX 0 N1 3 0.342785 0.358115 0.207375 11.00000 0.05630 0.04536 = 0.06082 -0.02775 0.01072 -0.01751 AFIX 43 H1 2 0.249854 0.316635 0.199079 11.00000 -1.20000 AFIX 0 N3 3 0.650851 0.396778 0.188441 11.00000 0.06172 0.05335 = 0.06378 -0.03178 0.01633 -0.01898 C2 1 0.536722 0.314719 0.162195 11.00000 0.07167 0.04494 = 0.04759 -0.02251 0.01436 -0.01200 AFIX 43 H2 2 0.587186 0.231726 0.115231 11.00000 -1.20000 AFIX 66 C5 1 0.376770 0.736213 0.366337 11.00000 0.05396 0.04045 = 0.05896 -0.02042 0.01017 -0.01605 C4 1 0.538478 0.638400 0.303637 11.00000 0.04699 0.04383 = 0.03377 -0.00868 0.00477 -0.01782 AFIX 43 H4 2 0.663585 0.657635 0.294067 11.00000 -1.20000 AFIX 65 C9 1 0.513198 0.511837 0.255242 11.00000 0.06839 0.04714 = 0.05186 -0.02648 0.01817 -0.02020 C8 1 0.326212 0.483087 0.269546 11.00000 0.06288 0.04435 = 0.05608 -0.02294 0.01853 -0.02418 C7 1 0.164502 0.580899 0.332246 11.00000 0.06078 0.05108 = 0.05092 -0.02524 0.02134 -0.02829 AFIX 43 H7 2 0.039395 0.561663 0.341816 11.00000 -1.20000 AFIX 65 C6 1 0.189778 0.707463 0.380642 11.00000 0.05157 0.04667 = 0.04553 -0.01973 0.00897 -0.02066 AFIX 0 C10 1 0.407657 0.873587 0.418599 11.00000 0.04961 0.04770 = 0.04959 -0.01825 -0.00202 -0.01480 AFIX 137 H10A 2 0.345896 0.991805 0.347252 11.00000 -1.50000 H10B 2 0.548901 0.856444 0.422927 11.00000 -1.50000 H10C 2 0.347713 0.859421 0.518679 11.00000 -1.50000 AFIX 0 C11 1 0.015949 0.815246 0.444335 11.00000 0.04661 0.04663 = 0.04583 -0.01867 -0.00046 -0.01196 AFIX 137 H11A 2 -0.013182 0.939105 0.377750 11.00000 -1.50000 H11B 2 0.047992 0.801647 0.544515 11.00000 -1.50000 H11C 2 -0.099216 0.774591 0.451871 11.00000 -1.50000 AFIX 0 HKLF 4 REM 36b in P-1 REM R1 = 0.0957 for 344 Fo > 4sig(Fo) and 0.1410 for all 582 data REM 119 parameters refined using 168 restraints END WGHT 0.1881 0.2349 REM Highest difference peak 0.210, deepest hole -0.166, 1-sigma level 0.050 Q1 1 0.1885 1.1408 0.2840 11.00000 0.05 0.21 Q2 1 -0.1222 0.3442 0.0458 11.00000 0.05 0.20 Q3 1 0.3988 0.4810 0.2994 11.00000 0.05 0.20 Q4 1 0.3722 0.5259 0.2474 11.00000 0.05 0.20 Q5 1 -0.1541 0.3597 0.0175 11.00000 0.05 0.20 Q6 1 0.6507 0.9606 0.2813 11.00000 0.05 0.17 Q7 1 0.6041 0.9957 0.4211 11.00000 0.05 0.15 Q8 1 0.4411 0.5210 0.0614 11.00000 0.05 0.14 Q9 1 0.3326 0.4782 0.4576 11.00000 0.05 0.14 Q10 1 0.2798 0.4985 0.4203 11.00000 0.05 0.14 ; _shelx_res_checksum 51126 _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 0.0459(18) 0.2497(10) 0.1606(12) 0.0540(18) Uani 1 1 d . U H1A H -0.0723 0.2651 0.1884 0.081 Uiso 1 1 calc GR . C12 C 0.066(3) 0.2437(15) 0.0124(19) 0.076(9) Uani 1 1 d . U H12A H 0.0989 0.3500 -0.0605 0.091 Uiso 1 1 calc R . H12B H -0.0609 0.2443 -0.0169 0.091 Uiso 1 1 calc R . C13 C 0.222(3) 0.0853(15) 0.005(2) 0.067(3) Uani 1 1 d . U H13A H 0.1939 -0.0202 0.0800 0.101 Uiso 1 1 calc GR . H13B H 0.3503 0.0895 0.0246 0.101 Uiso 1 1 calc GR . H13C H 0.2245 0.0825 -0.0959 0.101 Uiso 1 1 calc GR . N1 N 0.343(2) 0.3581(11) 0.2074(15) 0.052(7) Uani 1 1 d . U H1 H 0.2499 0.3166 0.1991 0.063 Uiso 1 1 calc R . N3 N 0.651(2) 0.3968(11) 0.1884(15) 0.058(7) Uani 1 1 d . U C2 C 0.537(3) 0.3147(14) 0.1622(19) 0.056(8) Uani 1 1 d . U H2 H 0.5872 0.2317 0.1152 0.067 Uiso 1 1 calc R . C5 C 0.3768(13) 0.7362(8) 0.3663(10) 0.051(7) Uani 1 1 d . U C4 C 0.5385(12) 0.6384(8) 0.3036(9) 0.043(8) Uani 1 1 d G U H4 H 0.6636 0.6576 0.2941 0.051 Uiso 1 1 calc R . C9 C 0.5132(13) 0.5118(8) 0.2552(10) 0.054(7) Uani 1 1 d G U C8 C 0.3262(13) 0.4831(8) 0.2695(10) 0.053(7) Uani 1 1 d G U C7 C 0.1645(12) 0.5809(8) 0.3322(9) 0.052(8) Uani 1 1 d G U H7 H 0.0394 0.5617 0.3418 0.062 Uiso 1 1 calc R . C6 C 0.1898(12) 0.7075(7) 0.3806(10) 0.047(7) Uani 1 1 d G U C10 C 0.408(3) 0.8736(14) 0.4186(18) 0.049(2) Uani 1 1 d . U H10A H 0.3459 0.9918 0.3473 0.073 Uiso 1 1 calc GR . H10B H 0.5489 0.8564 0.4229 0.073 Uiso 1 1 calc GR . H10C H 0.3477 0.8594 0.5187 0.073 Uiso 1 1 calc GR . C11 C 0.016(3) 0.8152(14) 0.4443(18) 0.046(2) Uani 1 1 d . U H11A H -0.0132 0.9391 0.3778 0.069 Uiso 1 1 calc GR . H11B H 0.0480 0.8016 0.5445 0.069 Uiso 1 1 calc GR . H11C H -0.0992 0.7746 0.4519 0.069 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 0.054(2) 0.0552(18) 0.053(2) -0.0222(12) 0.0003(11) -0.0138(11) C12 0.095(17) 0.072(7) 0.076(14) -0.046(9) 0.028(14) -0.034(9) C13 0.067(3) 0.067(3) 0.067(3) -0.0258(14) -0.0009(11) -0.0187(13) N1 0.056(14) 0.045(5) 0.061(10) -0.028(6) 0.011(11) -0.018(7) N3 0.062(13) 0.053(5) 0.064(11) -0.032(7) 0.016(11) -0.019(7) C2 0.072(14) 0.045(6) 0.048(12) -0.023(7) 0.014(12) -0.012(8) C5 0.054(14) 0.040(5) 0.059(12) -0.020(7) 0.010(11) -0.016(7) C4 0.047(14) 0.044(6) 0.034(12) -0.009(7) 0.005(12) -0.018(8) C9 0.068(13) 0.047(5) 0.052(11) -0.026(7) 0.018(11) -0.020(7) C8 0.063(13) 0.044(5) 0.056(11) -0.023(7) 0.019(11) -0.024(7) C7 0.061(14) 0.051(6) 0.051(12) -0.025(7) 0.021(12) -0.028(8) C6 0.052(13) 0.047(6) 0.046(11) -0.020(7) 0.009(11) -0.021(8) C10 0.050(2) 0.048(2) 0.050(2) -0.0182(12) -0.0020(11) -0.0148(12) C11 0.047(2) 0.047(2) 0.046(2) -0.0187(12) -0.0005(11) -0.0120(12) 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 109.1 O1 C12 H12B 109.1 O1 C12 C13 112.3(16) H12A C12 H12B 107.9 C13 C12 H12A 109.1 C13 C12 H12B 109.1 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 127.6 C2 N1 C8 104.8(11) C8 N1 H1 127.6 C2 N3 C9 102.6(9) N1 C2 H2 121.9 N3 C2 N1 116.1(7) N3 C2 H2 121.9 C4 C5 C6 120.0 C4 C5 C10 119.2(6) C6 C5 C10 120.8(6) C5 C4 H4 120.0 C9 C4 C5 120.0 C9 C4 H4 120.0 C4 C9 N3 131.1(6) C4 C9 C8 120.0 C8 C9 N3 108.9(6) N1 C8 C9 107.5(6) N1 C8 C7 132.5(7) C9 C8 C7 120.0 C8 C7 H7 120.0 C6 C7 C8 120.0 C6 C7 H7 120.0 C5 C6 C11 119.9(7) C7 C6 C5 120.0 C7 C6 C11 120.1(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 1.411(17) C12 H12A 0.9700 C12 H12B 0.9700 C12 C13 1.459(17) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 N1 H1 0.8600 N1 C2 1.347(17) N1 C8 1.372(8) N3 C2 1.319(19) N3 C9 1.416(6) C2 H2 0.9300 C5 C4 1.3900 C5 C6 1.3900 C5 C10 1.517(12) C4 H4 0.9300 C4 C9 1.3900 C9 C8 1.3900 C8 C7 1.3900 C7 H7 0.9300 C7 C6 1.3900 C6 C11 1.487(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_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N3 0.82 1.91 2.678(16) 155.8 1_455 N1 H1 O1 0.86 1.83 2.684(17) 173.5 . 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 -176.7(11) N3 C9 C8 N1 -2.4(10) N3 C9 C8 C7 -179.9(8) C2 N1 C8 C9 1.3(13) C2 N1 C8 C7 178.3(10) C2 N3 C9 C4 -177.4(9) C2 N3 C9 C8 2.5(11) C5 C4 C9 N3 179.9(10) C5 C4 C9 C8 0.0 C4 C5 C6 C7 0.0 C4 C5 C6 C11 -178.6(9) C4 C9 C8 N1 177.5(9) C4 C9 C8 C7 0.0 C9 N3 C2 N1 -1.8(16) C9 C8 C7 C6 0.0 C8 N1 C2 N3 0.3(17) C8 C7 C6 C5 0.0 C8 C7 C6 C11 178.6(9) C6 C5 C4 C9 0.0 C10 C5 C4 C9 179.9(10) C10 C5 C6 C7 -179.9(10) C10 C5 C6 C11 1.5(12)