#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:32:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180477 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/46/7214602.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_7214602
loop_
_publ_author_name
'Shida, Toshihide'
'Mutai, Toshiki'
'Araki, Koji'
_publ_section_title
;
 Sterically induced polymorphism: ON--OFF control of excited-state
 intramolecular proton transfer (ESIPT) luminescence of
 1-methyl-2-(2′-hydroxyphenyl)benzimidazole
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              10179
_journal_paper_doi               10.1039/c3ce41742e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.615(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.516(1)
_cell_length_b                   15.318(1)
_cell_length_c                   11.199(1)
_cell_measurement_reflns_used    10352
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      73.20
_cell_measurement_theta_min      5.22
_cell_volume                     1172.2(2)
_computing_cell_refinement       Scalepack
_computing_data_collection       'MacScience Xpress'
_computing_data_reduction        'Denzo and Scalepack'
_computing_molecular_graphics    maXus
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'MacScience DIPLabo'
_diffrn_measurement_method       IP
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10352
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.20
_diffrn_reflns_theta_min         5.22
_diffrn_standards_decay_%        NONE
_diffrn_standards_interval_count NONE
_diffrn_standards_interval_time  NONE
_diffrn_standards_number         NONE
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.9108
_exptl_absorpt_correction_T_min  0.8396
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'abscor (MacScience Co. Ltd., 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.3870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                2102
_reflns_number_total             2305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41742e.txt
_cod_data_source_block           MeHBINL
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7214602
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'
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
O1 O 0.2095(2) 0.77082(9) 0.59741(14) 0.0545(4) Uani 1 1 d .
H1 H 0.2175 0.7967 0.6636 0.082 Uiso 1 1 calc R
C1 C 0.3571(3) 0.79605(12) 0.56664(17) 0.0443(4) Uani 1 1 d .
C2 C 0.4590(3) 0.87362(13) 0.6126(2) 0.0562(5) Uani 1 1 d .
H2 H 0.4286 0.9092 0.6688 0.067 Uiso 1 1 calc R
C3 C 0.6050(3) 0.89800(15) 0.5750(2) 0.0646(6) Uani 1 1 d .
H3 H 0.6740 0.9494 0.6075 0.078 Uiso 1 1 calc R
C4 C 0.6496(3) 0.84713(16) 0.4900(2) 0.0649(6) Uani 1 1 d .
H4 H 0.7469 0.8644 0.4642 0.078 Uiso 1 1 calc R
C5 C 0.5490(3) 0.77046(14) 0.4436(2) 0.0535(5) Uani 1 1 d .
H5 H 0.5783 0.7363 0.3855 0.064 Uiso 1 1 calc R
C6 C 0.4041(3) 0.74318(11) 0.48209(16) 0.0420(4) Uani 1 1 d .
C7 C 0.3055(3) 0.65938(11) 0.43251(16) 0.0408(4) Uani 1 1 d .
N1 N 0.3045(2) 0.59214(9) 0.51204(14) 0.0434(4) Uani 1 1 d .
C8 C 0.4000(3) 0.58880(14) 0.65439(18) 0.0547(5) Uani 1 1 d .
H6 H 0.3036 0.5945 0.6894 0.082 Uiso 1 1 calc R
H7 H 0.4926 0.6357 0.6864 0.082 Uiso 1 1 calc R
H8 H 0.4668 0.5340 0.6816 0.082 Uiso 1 1 calc R
C9 C 0.2139(3) 0.52234(11) 0.43132(18) 0.0447(4) Uani 1 1 d .
C10 C 0.1773(3) 0.43734(13) 0.4587(2) 0.0594(5) Uani 1 1 d .
H9 H 0.2112 0.4181 0.5442 0.071 Uiso 1 1 calc R
C11 C 0.0877(3) 0.38304(15) 0.3514(3) 0.0701(7) Uani 1 1 d .
H10 H 0.0619 0.3255 0.3653 0.084 Uiso 1 1 calc R
C12 C 0.0353(3) 0.41189(16) 0.2241(3) 0.0692(6) Uani 1 1 d .
H11 H -0.0255 0.3733 0.1548 0.083 Uiso 1 1 calc R
C13 C 0.0709(3) 0.49610(15) 0.1975(2) 0.0596(5) Uani 1 1 d .
H12 H 0.0350 0.5150 0.1116 0.072 Uiso 1 1 calc R
C14 C 0.1627(3) 0.55203(12) 0.30367(18) 0.0456(4) Uani 1 1 d .
N2 N 0.2208(2) 0.63821(10) 0.30660(14) 0.0459(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 H1 109.5
O1 C1 C2 122.35(17)
O1 C1 C6 118.27(16)
C2 C1 C6 119.35(17)
C3 C2 C1 120.21(19)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.77(19)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 119.44(19)
C3 C4 H4 120.3
C5 C4 H4 120.3
C4 C5 C6 121.09(19)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 119.12(17)
C5 C6 C7 118.77(16)
C1 C6 C7 122.11(16)
N2 C7 N1 112.33(15)
N2 C7 C6 124.01(15)
N1 C7 C6 123.48(15)
C7 N1 C9 107.00(14)
C7 N1 C8 127.55(16)
C9 N1 C8 125.06(15)
N1 C8 H6 109.5
N1 C8 H7 109.5
H6 C8 H7 109.5
N1 C8 H8 109.5
H6 C8 H8 109.5
H7 C8 H8 109.5
N1 C9 C10 131.96(18)
N1 C9 C14 105.59(15)
C10 C9 C14 122.43(19)
C11 C10 C9 116.2(2)
C11 C10 H9 121.9
C9 C10 H9 121.9
C10 C11 C12 121.9(2)
C10 C11 H10 119.0
C12 C11 H10 119.0
C13 C12 C11 121.7(2)
C13 C12 H11 119.1
C11 C12 H11 119.1
C12 C13 C14 117.6(2)
C12 C13 H12 121.2
C14 C13 H12 121.2
N2 C14 C9 109.69(16)
N2 C14 C13 130.15(18)
C9 C14 C13 120.15(19)
C7 N2 C14 105.40(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.348(2)
O1 H1 0.8200
C1 C2 1.391(3)
C1 C6 1.398(2)
C2 C3 1.381(3)
C2 H2 0.9300
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.376(3)
C4 H4 0.9300
C5 C6 1.392(3)
C5 H5 0.9300
C6 C7 1.470(2)
C7 N2 1.323(2)
C7 N1 1.364(2)
N1 C9 1.383(2)
N1 C8 1.451(2)
C8 H6 0.9600
C8 H7 0.9600
C8 H8 0.9600
C9 C10 1.391(3)
C9 C14 1.393(3)
C10 C11 1.384(3)
C10 H9 0.9300
C11 C12 1.384(4)
C11 H10 0.9300
C12 C13 1.375(3)
C12 H11 0.9300
C13 C14 1.393(3)
C13 H12 0.9300
C14 N2 1.387(2)
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
O1 C1 C2 C3 -177.9(2)
C6 C1 C2 C3 0.0(3)
C1 C2 C3 C4 1.2(4)
C2 C3 C4 C5 -0.9(4)
C3 C4 C5 C6 -0.6(4)
C4 C5 C6 C1 1.7(3)
C4 C5 C6 C7 -178.17(19)
O1 C1 C6 C5 176.59(17)
C2 C1 C6 C5 -1.4(3)
O1 C1 C6 C7 -3.5(3)
C2 C1 C6 C7 178.48(17)
C5 C6 C7 N2 -53.2(3)
C1 C6 C7 N2 126.9(2)
C5 C6 C7 N1 121.4(2)
C1 C6 C7 N1 -58.5(2)
N2 C7 N1 C9 0.5(2)
C6 C7 N1 C9 -174.73(15)
N2 C7 N1 C8 173.55(16)
C6 C7 N1 C8 -1.7(3)
C7 N1 C9 C10 178.1(2)
C8 N1 C9 C10 4.8(3)
C7 N1 C9 C14 -0.23(19)
C8 N1 C9 C14 -173.52(16)
N1 C9 C10 C11 -177.67(19)
C14 C9 C10 C11 0.4(3)
C9 C10 C11 C12 -0.7(3)
C10 C11 C12 C13 0.5(4)
C11 C12 C13 C14 0.2(3)
N1 C9 C14 N2 -0.1(2)
C10 C9 C14 N2 -178.60(17)
N1 C9 C14 C13 178.69(16)
C10 C9 C14 C13 0.2(3)
C12 C13 C14 N2 178.0(2)
C12 C13 C14 C9 -0.4(3)
N1 C7 N2 C14 -0.5(2)
C6 C7 N2 C14 174.67(16)
C9 C14 N2 C7 0.3(2)
C13 C14 N2 C7 -178.24(19)
