# 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. 
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data_HPBI_II_90K
_database_code_depnum_ccdc_archive 'CCDC 879973'
#TrackingRef '11058_web_deposit_cif_file_1_KiichiAmimoto_1336004896.HPBI_II_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         210.24
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.8136(4)
_cell_length_b                   4.7190(1)
_cell_length_c                   12.9222(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.450(1)
_cell_angle_gamma                90
_cell_volume                     1001.18(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    8057
_cell_measurement_theta_min      2.4811
_cell_measurement_theta_max      28.5459
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.091
_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  0.0138
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_number            4725
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.915
_reflns_number_total             2347
_reflns_number_gt                2244
_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^)+(0.0530P)^2^+0.6157P] 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       0.009(2)
_refine_ls_number_reflns         2347
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.4
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
# 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 0.003 0.002 '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 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 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
H2N H 0.2592(11) -0.130(4) 0.8128(15) 0.037(5) Uiso 1 1 d . . .
H1O H 0.2558(13) -0.067(5) 0.4784(17) 0.053(6) Uiso 1 1 d . . .
N1 N 0.21785(6) 0.0700(2) 0.57651(8) 0.0158(2) Uani 1 1 d . . .
O1 O 0.29172(6) -0.1933(2) 0.45113(7) 0.0202(2) Uani 1 1 d . . .
C1 C 0.31956(7) -0.2987(2) 0.63853(9) 0.0151(2) Uani 1 1 d . . .
N2 N 0.23979(6) -0.0345(2) 0.74921(8) 0.0154(2) Uani 1 1 d . . .
C12 C 0.13965(7) 0.3108(3) 0.80004(10) 0.0180(3) Uani 1 1 d . . .
H12 H 0.1491 0.2664 0.8718 0.022 Uiso 1 1 calc R . .
C6 C 0.36379(7) -0.4607(3) 0.72215(10) 0.0176(3) Uani 1 1 d . . .
H6 H 0.3549 -0.4353 0.7901 0.021 Uiso 1 1 calc R . .
C8 C 0.16750(7) 0.2384(3) 0.62330(9) 0.0152(2) Uani 1 1 d . . .
C11 C 0.08368(7) 0.5163(3) 0.75587(10) 0.0199(3) Uani 1 1 d . . .
H11 H 0.0549 0.6123 0.7989 0.024 Uiso 1 1 calc R . .
C7 C 0.25948(7) -0.0898(2) 0.65425(9) 0.0150(2) Uani 1 1 d . . .
C4 C 0.43420(7) -0.6961(3) 0.60348(11) 0.0209(3) Uani 1 1 d . . .
H4 H 0.4725 -0.8277 0.592 0.025 Uiso 1 1 calc R . .
C13 C 0.18109(7) 0.1740(2) 0.73186(9) 0.0155(2) Uani 1 1 d . . .
C2 C 0.33359(7) -0.3412(3) 0.53592(9) 0.0168(3) Uani 1 1 d . . .
C3 C 0.39102(7) -0.5388(3) 0.51941(10) 0.0204(3) Uani 1 1 d . . .
H3 H 0.4004 -0.5653 0.4517 0.024 Uiso 1 1 calc R . .
C5 C 0.42053(7) -0.6581(3) 0.70519(10) 0.0199(3) Uani 1 1 d . . .
H5 H 0.4494 -0.7649 0.7614 0.024 Uiso 1 1 calc R . .
C9 C 0.11105(7) 0.4467(3) 0.58023(9) 0.0185(3) Uani 1 1 d . . .
H9 H 0.1017 0.4928 0.5086 0.022 Uiso 1 1 calc R . .
C10 C 0.06947(7) 0.5825(3) 0.64755(10) 0.0194(3) Uani 1 1 d . . .
H10 H 0.0312 0.7207 0.6203 0.023 Uiso 1 1 calc R . .

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
N1 0.0170(5) 0.0158(5) 0.0146(5) -0.0007(4) 0.0033(4) -0.0002(4)
O1 0.0247(5) 0.0225(5) 0.0139(4) -0.0010(3) 0.0052(3) 0.0036(4)
C1 0.0150(5) 0.0144(5) 0.0163(5) -0.0014(4) 0.0043(4) -0.0031(4)
N2 0.0169(5) 0.0164(5) 0.0136(5) 0.0005(4) 0.0047(4) -0.0010(4)
C12 0.0186(5) 0.0200(6) 0.0170(5) -0.0014(4) 0.0073(4) -0.0038(4)
C6 0.0175(5) 0.0176(6) 0.0178(5) -0.0003(4) 0.0043(4) -0.0028(4)
C8 0.0148(5) 0.0162(5) 0.0152(5) -0.0016(4) 0.0048(4) -0.0026(4)
C11 0.0193(6) 0.0190(6) 0.0233(6) -0.0042(5) 0.0086(5) -0.0022(4)
C7 0.0161(5) 0.0151(5) 0.0141(5) -0.0008(4) 0.0038(4) -0.0034(4)
C4 0.0175(6) 0.0170(6) 0.0288(7) -0.0028(5) 0.0062(5) -0.0001(4)
C13 0.0155(5) 0.0147(5) 0.0162(5) 0.0002(4) 0.0030(4) -0.0028(4)
C2 0.0179(5) 0.0163(5) 0.0165(5) -0.0014(4) 0.0041(4) -0.0034(4)
C3 0.0215(6) 0.0204(6) 0.0207(6) -0.0039(5) 0.0079(5) -0.0018(5)
C5 0.0175(6) 0.0173(6) 0.0238(6) 0.0020(5) 0.0020(4) -0.0005(4)
C9 0.0195(6) 0.0184(6) 0.0167(5) 0.0000(4) 0.0021(4) -0.0005(4)
C10 0.0158(5) 0.0180(6) 0.0243(6) -0.0010(5) 0.0043(4) 0.0002(4)


#----------------------------------------------------------------------------#
# 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
N1 C7 1.3283(15) . ?
N1 C8 1.3908(15) . ?
O1 C2 1.3604(15) . ?
O1 H1O 0.97(2) . ?
C1 C6 1.3994(16) . ?
C1 C2 1.4103(16) . ?
C1 C7 1.4567(16) . ?
N2 C7 1.3633(14) . ?
N2 C13 1.3771(15) . ?
N2 H2N 0.932(19) . ?
C12 C11 1.3855(18) . ?
C12 C13 1.3941(16) . ?
C12 H12 0.93 . ?
C6 C5 1.3845(17) . ?
C6 H6 0.93 . ?
C8 C9 1.3962(17) . ?
C8 C13 1.4052(16) . ?
C11 C10 1.4034(18) . ?
C11 H11 0.93 . ?
C4 C3 1.3849(18) . ?
C4 C5 1.3938(18) . ?
C4 H4 0.93 . ?
C2 C3 1.3915(17) . ?
C3 H3 0.93 . ?
C5 H5 0.93 . ?
C9 C10 1.3851(17) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?

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
C7 N1 C8 105.45(10) . . ?
C2 O1 H1O 106.2(13) . . ?
C6 C1 C2 118.65(11) . . ?
C6 C1 C7 122.08(11) . . ?
C2 C1 C7 119.27(11) . . ?
C7 N2 C13 107.15(10) . . ?
C7 N2 H2N 126.5(12) . . ?
C13 N2 H2N 126.2(12) . . ?
C11 C12 C13 116.84(11) . . ?
C11 C12 H12 121.6 . . ?
C13 C12 H12 121.6 . . ?
C5 C6 C1 121.00(11) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C8 C9 130.85(11) . . ?
N1 C8 C13 109.10(10) . . ?
C9 C8 C13 120.04(11) . . ?
C12 C11 C10 121.41(11) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
N1 C7 N2 112.42(10) . . ?
N1 C7 C1 123.15(10) . . ?
N2 C7 C1 124.42(10) . . ?
C3 C4 C5 120.38(12) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N2 C13 C12 131.79(11) . . ?
N2 C13 C8 105.88(10) . . ?
C12 C13 C8 122.33(11) . . ?
O1 C2 C3 118.43(11) . . ?
O1 C2 C1 121.45(11) . . ?
C3 C2 C1 120.12(11) . . ?
C4 C3 C2 120.17(11) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C6 C5 C4 119.67(11) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C10 C9 C8 117.84(11) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 121.54(12) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?

# END of CIF