#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301864 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/46/7214603.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_7214603
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         'C17 H18 N2 O'
_chemical_formula_sum            'C17 H18 N2 O'
_chemical_formula_weight         266.33
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   21.216(1)
_cell_length_b                   21.216
_cell_length_c                   17.221(1)
_cell_measurement_reflns_used    21369
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      73.52
_cell_measurement_theta_min      3.52
_cell_volume                     6713.0(5)
_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 1.000
_diffrn_measured_fraction_theta_max 0.987
_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  0.055
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21369
_diffrn_reflns_theta_full        67.44
_diffrn_reflns_theta_max         73.52
_diffrn_reflns_theta_min         3.52
_diffrn_standards_decay_%        NONE
_diffrn_standards_interval_count NONE
_diffrn_standards_interval_time  NONE
_diffrn_standards_number         NONE
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  0.8902
_exptl_absorpt_correction_T_min  0.8366
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'abscor (MacScience Co. Ltd., 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2556
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0624
_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)+(0.0627P)²+6.2483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                2648
_reflns_number_total             2958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41742e.txt
_cod_data_source_block           tBuHBI
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7214603
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.38319(7) 0.44382(7) 0.16977(8) 0.0571(4) Uani 1 1 d .
H1 H 0.4262 0.4742 0.1634 0.086 Uiso 1 1 calc R
C1 C 0.35352(9) 0.46914(9) 0.22205(10) 0.0460(4) Uani 1 1 d .
C2 C 0.38564(11) 0.54201(10) 0.24236(13) 0.0604(5) Uani 1 1 d .
H2 H 0.4288 0.5761 0.2187 0.072 Uiso 1 1 calc R
C3 C 0.35367(13) 0.56387(12) 0.29762(16) 0.0759(7) Uani 1 1 d .
H3 H 0.3758 0.6128 0.3113 0.091 Uiso 1 1 calc R
C4 C 0.28943(13) 0.51454(12) 0.33291(16) 0.0758(7) Uani 1 1 d .
H4 H 0.2689 0.5295 0.3712 0.091 Uiso 1 1 calc R
C5 C 0.25606(11) 0.44249(11) 0.31057(12) 0.0593(5) Uani 1 1 d .
H5 H 0.2116 0.4092 0.3325 0.071 Uiso 1 1 calc R
C6 C 0.28784(9) 0.41904(9) 0.25584(10) 0.0438(4) Uani 1 1 d .
C7 C 0.24672(8) 0.34335(9) 0.22652(9) 0.0407(4) Uani 1 1 d .
N1 N 0.26237(7) 0.28830(7) 0.23515(8) 0.0420(3) Uani 1 1 d .
C8 C 0.31877(10) 0.28347(10) 0.28308(11) 0.0518(4) Uani 1 1 d .
C9 C 0.36119(13) 0.34976(13) 0.33429(13) 0.0684(6) Uani 1 1 d .
H6 H 0.3282 0.3554 0.3678 0.103 Uiso 1 1 calc R
H7 H 0.3869 0.3923 0.3024 0.103 Uiso 1 1 calc R
H8 H 0.3954 0.3435 0.3651 0.103 Uiso 1 1 calc R
C10 C 0.37107(12) 0.27631(13) 0.22735(15) 0.0702(6) Uani 1 1 d .
H9 H 0.3930 0.3178 0.1935 0.105 Uiso 1 1 calc R
H10 H 0.3447 0.2328 0.1970 0.105 Uiso 1 1 calc R
H11 H 0.4083 0.2738 0.2566 0.105 Uiso 1 1 calc R
C11 C 0.27915(15) 0.21725(13) 0.33648(15) 0.0779(7) Uani 1 1 d .
H12 H 0.2529 0.1741 0.3056 0.117 Uiso 1 1 calc R
H13 H 0.2457 0.2231 0.3690 0.117 Uiso 1 1 calc R
H14 H 0.3140 0.2130 0.3683 0.117 Uiso 1 1 calc R
C12 C 0.21036(9) 0.23029(9) 0.19098(10) 0.0442(4) Uani 1 1 d .
C13 C 0.19874(11) 0.16126(11) 0.17370(13) 0.0614(5) Uani 1 1 d .
H15 H 0.2282 0.1447 0.1946 0.074 Uiso 1 1 calc R
C14 C 0.14207(13) 0.11834(13) 0.12454(15) 0.0740(7) Uani 1 1 d .
H16 H 0.1333 0.0719 0.1124 0.089 Uiso 1 1 calc R
C15 C 0.09769(12) 0.14226(13) 0.09262(15) 0.0726(6) Uani 1 1 d .
H17 H 0.0602 0.1119 0.0593 0.087 Uiso 1 1 calc R
C16 C 0.10844(10) 0.20972(12) 0.10950(13) 0.0622(5) Uani 1 1 d .
H18 H 0.0787 0.2258 0.0882 0.075 Uiso 1 1 calc R
C17 C 0.16522(9) 0.25395(10) 0.15951(10) 0.0456(4) Uani 1 1 d .
N2 N 0.18883(7) 0.32460(8) 0.18317(8) 0.0453(3) 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 122.90(16)
O1 C1 C6 117.54(15)
C2 C1 C6 119.55(17)
C3 C2 C1 119.98(19)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 121.1(2)
C2 C3 H3 119.5
C4 C3 H3 119.5
C3 C4 C5 118.9(2)
C3 C4 H4 120.5
C5 C4 H4 120.5
C4 C5 C6 120.96(19)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 119.44(16)
C5 C6 C7 119.46(15)
C1 C6 C7 120.57(15)
N2 C7 N1 112.96(14)
N2 C7 C6 118.39(14)
N1 C7 C6 128.58(14)
C7 N1 C12 105.67(13)
C7 N1 C8 131.22(14)
C12 N1 C8 123.04(14)
N1 C8 C9 112.38(15)
N1 C8 C10 107.74(15)
C9 C8 C10 109.45(18)
N1 C8 C11 107.62(16)
C9 C8 C11 107.49(18)
C10 C8 C11 112.21(18)
C8 C9 H6 109.5
C8 C9 H7 109.5
H6 C9 H7 109.5
C8 C9 H8 109.5
H6 C9 H8 109.5
H7 C9 H8 109.5
C8 C10 H9 109.5
C8 C10 H10 109.5
H9 C10 H10 109.5
C8 C10 H11 109.5
H9 C10 H11 109.5
H10 C10 H11 109.5
C8 C11 H12 109.5
C8 C11 H13 109.5
H12 C11 H13 109.5
C8 C11 H14 109.5
H12 C11 H14 109.5
H13 C11 H14 109.5
C13 C12 C17 120.27(17)
C13 C12 N1 133.65(16)
C17 C12 N1 106.05(14)
C14 C13 C12 117.67(19)
C14 C13 H15 121.2
C12 C13 H15 121.2
C13 C14 C15 122.0(2)
C13 C14 H16 119.0
C15 C14 H16 119.0
C16 C15 C14 120.8(2)
C16 C15 H17 119.6
C14 C15 H17 119.6
C15 C16 C17 118.2(2)
C15 C16 H18 120.9
C17 C16 H18 120.9
N2 C17 C12 109.51(15)
N2 C17 C16 129.37(17)
C12 C17 C16 121.06(17)
C7 N2 C17 105.78(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.354(2)
O1 H1 0.8200
C1 C2 1.387(3)
C1 C6 1.389(2)
C2 C3 1.377(3)
C2 H2 0.9300
C3 C4 1.377(3)
C3 H3 0.9300
C4 C5 1.380(3)
C4 H4 0.9300
C5 C6 1.388(2)
C5 H5 0.9300
C6 C7 1.481(2)
C7 N2 1.317(2)
C7 N1 1.373(2)
N1 C12 1.397(2)
N1 C8 1.499(2)
C8 C9 1.517(3)
C8 C10 1.531(3)
C8 C11 1.531(3)
C9 H6 0.9600
C9 H7 0.9600
C9 H8 0.9600
C10 H9 0.9600
C10 H10 0.9600
C10 H11 0.9600
C11 H12 0.9600
C11 H13 0.9600
C11 H14 0.9600
C12 C13 1.390(3)
C12 C17 1.394(2)
C13 C14 1.377(3)
C13 H15 0.9300
C14 C15 1.387(3)
C14 H16 0.9300
C15 C16 1.363(3)
C15 H17 0.9300
C16 C17 1.394(3)
C16 H18 0.9300
C17 N2 1.383(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 -178.1(2)
C6 C1 C2 C3 2.2(3)
C1 C2 C3 C4 -0.7(4)
C2 C3 C4 C5 -1.7(4)
C3 C4 C5 C6 2.7(4)
C4 C5 C6 C1 -1.2(3)
C4 C5 C6 C7 -173.0(2)
O1 C1 C6 C5 179.06(17)
C2 C1 C6 C5 -1.2(3)
O1 C1 C6 C7 -9.3(2)
C2 C1 C6 C7 170.39(17)
C5 C6 C7 N2 68.0(2)
C1 C6 C7 N2 -103.67(19)
C5 C6 C7 N1 -115.4(2)
C1 C6 C7 N1 72.9(2)
N2 C7 N1 C12 1.85(18)
C6 C7 N1 C12 -174.90(16)
N2 C7 N1 C8 -175.09(16)
C6 C7 N1 C8 8.2(3)
C7 N1 C8 C9 4.9(3)
C12 N1 C8 C9 -171.61(17)
C7 N1 C8 C10 -115.77(19)
C12 N1 C8 C10 67.7(2)
C7 N1 C8 C11 123.0(2)
C12 N1 C8 C11 -53.5(2)
C7 N1 C12 C13 177.0(2)
C8 N1 C12 C13 -5.7(3)
C7 N1 C12 C17 -1.24(17)
C8 N1 C12 C17 176.02(15)
C17 C12 C13 C14 0.5(3)
N1 C12 C13 C14 -177.6(2)
C12 C13 C14 C15 0.2(4)
C13 C14 C15 C16 -0.5(4)
C14 C15 C16 C17 0.1(3)
C13 C12 C17 N2 -178.23(16)
N1 C12 C17 N2 0.32(18)
C13 C12 C17 C16 -0.9(3)
N1 C12 C17 C16 177.64(16)
C15 C16 C17 N2 177.3(2)
C15 C16 C17 C12 0.6(3)
N1 C7 N2 C17 -1.65(18)
C6 C7 N2 C17 175.46(14)
C12 C17 N2 C7 0.78(18)
C16 C17 N2 C7 -176.25(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 136161929
