# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_HPBI_I_90K _database_code_depnum_ccdc_archive 'CCDC 879972' #TrackingRef '11057_web_deposit_cif_file_0_KiichiAmimoto_1336004896.HPBI_I_90K_ccdc_deposit.cif' _audit_creation_date 2011-12-03 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-(2'-hydroxyphenyl)benzimidazole ; _chemical_formula_moiety 'C13 H10 N2 O1' _chemical_formula_sum 'C13 H10 N2 O' _chemical_formula_weight 210.23 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.7658(16) _cell_length_b 22.030(9) _cell_length_c 5.801(2) _cell_angle_alpha 90 _cell_angle_beta 94.516(5) _cell_angle_gamma 90 _cell_volume 479.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 1883 _cell_measurement_theta_min 3.5229 _cell_measurement_theta_max 28.0816 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_method 'phi and omega scan' _diffrn_measurement_device_type 'CCD area detector' _diffrn_detector_area_resol_mean 8.333 _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_unetI/netI 0.0666 _diffrn_reflns_number 2308 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.08 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.958 _reflns_number_total 1968 _reflns_number_gt 1783 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'WinGX (Farrugia, 1999) and publCIF (Westrip,2010)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.075(11) _refine_ls_number_reflns 1968 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.3(15) _refine_diff_density_max 0.322 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4705(5) 0.28230(9) -0.2566(3) 0.0139(4) Uani 1 1 d . . . C2 C 0.6443(5) 0.29685(9) -0.0394(3) 0.0152(5) Uani 1 1 d . . . C3 C 0.7517(6) 0.35608(9) 0.0100(3) 0.0177(5) Uani 1 1 d . . . H3 H 0.8652 0.3657 0.1575 0.021 Uiso 1 1 calc R . . C4 C 0.6944(5) 0.40109(10) -0.1542(4) 0.0192(5) Uani 1 1 d . . . H4 H 0.7676 0.4415 -0.1192 0.023 Uiso 1 1 calc R . . C5 C 0.5290(6) 0.38722(9) -0.3717(3) 0.0184(5) Uani 1 1 d . . . H5 H 0.4931 0.418 -0.4857 0.022 Uiso 1 1 calc R . . C6 C 0.4183(5) 0.32891(9) -0.4203(3) 0.0160(4) Uani 1 1 d . . . H6 H 0.3038 0.3199 -0.5681 0.019 Uiso 1 1 calc R . . C7 C 0.3492(6) 0.22090(9) -0.3023(3) 0.0141(4) Uani 1 1 d . . . C8 C 0.2482(5) 0.12447(9) -0.2636(3) 0.0150(5) Uani 1 1 d . . . C9 C 0.2264(6) 0.06454(10) -0.1891(3) 0.0176(5) Uani 1 1 d . . . H9 H 0.3237 0.0525 -0.0401 0.021 Uiso 1 1 calc R . . C10 C 0.0576(6) 0.02318(10) -0.3406(3) 0.0192(5) Uani 1 1 d . . . H10 H 0.0387 -0.0179 -0.2939 0.023 Uiso 1 1 calc R . . C11 C -0.0863(6) 0.04046(10) -0.5614(3) 0.0199(5) Uani 1 1 d . . . H11 H -0.1982 0.0107 -0.661 0.024 Uiso 1 1 calc R . . C12 C -0.0687(5) 0.10014(9) -0.6374(4) 0.0172(5) Uani 1 1 d . . . H12 H -0.1679 0.1122 -0.786 0.021 Uiso 1 1 calc R . . C13 C 0.1016(5) 0.14118(10) -0.4846(3) 0.0153(4) Uani 1 1 d . . . N1 N 0.4028(4) 0.17544(8) -0.1540(3) 0.0155(4) Uani 1 1 d . . . N2 N 0.1701(5) 0.20223(8) -0.5057(3) 0.0156(4) Uani 1 1 d . . . O1 O 0.7089(4) 0.25324(6) 0.1262(2) 0.0191(4) Uani 1 1 d . . . H1O H 0.611(9) 0.2130(16) 0.057(5) 0.050(9) Uiso 1 1 d . . . H2N H 0.086(7) 0.2266(12) -0.614(5) 0.027(7) Uiso 1 1 d . . . 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 C1 0.0167(10) 0.0128(10) 0.0113(9) -0.0010(8) -0.0038(7) 0.0025(8) C2 0.0164(10) 0.0160(12) 0.0124(10) 0.0009(8) -0.0043(8) 0.0018(8) C3 0.0214(11) 0.0167(12) 0.0136(10) -0.0014(8) -0.0059(8) 0.0006(8) C4 0.0200(11) 0.0174(11) 0.0196(11) -0.0017(8) -0.0023(9) -0.0004(9) C5 0.0241(11) 0.0162(11) 0.0142(10) 0.0028(8) -0.0034(8) 0.0038(9) C6 0.0188(11) 0.0162(11) 0.0121(10) 0.0005(8) -0.0044(8) 0.0020(9) C7 0.0146(10) 0.0175(11) 0.0095(10) -0.0017(8) -0.0030(7) -0.0001(8) C8 0.0171(12) 0.0161(11) 0.0112(9) -0.0025(8) -0.0025(8) -0.0004(8) C9 0.0239(12) 0.0156(11) 0.0123(10) 0.0008(8) -0.0040(9) 0.0007(8) C10 0.0227(12) 0.0147(10) 0.0200(11) -0.0001(9) -0.0004(8) 0.0010(9) C11 0.0248(13) 0.0179(12) 0.0163(10) -0.0039(9) -0.0028(9) -0.0019(9) C12 0.0191(11) 0.0165(11) 0.0151(10) -0.0034(8) -0.0040(8) 0.0002(9) C13 0.0189(11) 0.0132(10) 0.0137(9) -0.0002(8) 0.0002(8) 0.0008(8) N1 0.0187(10) 0.0124(8) 0.0144(8) -0.0012(7) -0.0040(6) 0.0002(8) N2 0.0204(10) 0.0130(9) 0.0120(9) 0.0007(7) -0.0062(7) 0.0005(7) O1 0.0285(8) 0.0142(8) 0.0128(7) 0.0032(6) -0.0103(6) -0.0015(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.402(3) . ? C1 C2 1.410(3) . ? C1 C7 1.446(3) . ? C2 O1 1.367(2) . ? C2 C3 1.389(3) . ? C3 C4 1.380(3) . ? C3 H3 0.95 . ? C4 C5 1.396(3) . ? C4 H4 0.95 . ? C5 C6 1.373(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 N1 1.325(3) . ? C7 N2 1.375(3) . ? C8 C9 1.394(3) . ? C8 N1 1.395(3) . ? C8 C13 1.404(3) . ? C9 C10 1.385(3) . ? C9 H9 0.95 . ? C10 C11 1.403(3) . ? C10 H10 0.95 . ? C11 C12 1.390(3) . ? C11 H11 0.95 . ? C12 C13 1.387(3) . ? C12 H12 0.95 . ? C13 N2 1.377(3) . ? N2 H2N 0.87(3) . ? O1 H1O 1.03(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.98(19) . . ? C6 C1 C7 122.39(17) . . ? C2 C1 C7 119.62(17) . . ? O1 C2 C3 118.86(17) . . ? O1 C2 C1 120.84(18) . . ? C3 C2 C1 120.30(18) . . ? C4 C3 C2 120.38(18) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4 120 . . ? C5 C4 H4 120 . . ? C6 C5 C4 119.80(19) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 121.48(18) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? N1 C7 N2 111.74(18) . . ? N1 C7 C1 123.93(17) . . ? N2 C7 C1 124.32(18) . . ? C9 C8 N1 130.83(18) . . ? C9 C8 C13 120.19(19) . . ? N1 C8 C13 108.98(17) . . ? C10 C9 C8 117.49(19) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? C9 C10 C11 121.7(2) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C10 121.43(19) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 116.41(19) . . ? C13 C12 H12 121.8 . . ? C11 C12 H12 121.8 . . ? N2 C13 C12 131.31(19) . . ? N2 C13 C8 105.92(18) . . ? C12 C13 C8 122.8(2) . . ? C7 N1 C8 105.99(15) . . ? C7 N2 C13 107.37(17) . . ? C7 N2 H2N 124.3(17) . . ? C13 N2 H2N 127.5(17) . . ? C2 O1 H1O 107.1(17) . . ?