#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/13/2231392.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2231392
loop_
_publ_author_name
'Fang, Xu-Bin'
'Fang, Lei'
'Liu, Xu-Ying'
_publ_section_title
;
 6-Methoxy-2-methyl-1-m-tolyl-1H-benzimidazole
 hemihydrate
;
_journal_coeditor_code           AA2011
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2263
_journal_paper_doi               10.1107/S1600536811031060
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H16 N2 O1, 0.5H2 O'
_chemical_formula_moiety         'C16 H16 N2 O1, 0.5(H2O)'
_chemical_formula_sum            'C16 H17 N2 O1.5'
_chemical_formula_weight         261.32
_chemical_name_systematic
;
6-Methoxy-2-methyl-1-m-tolyl-1H-benzimidazole hemihydrate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.0752(16)
_cell_length_b                   13.9140(14)
_cell_length_c                   12.6450(13)
_cell_measurement_reflns_used    2720
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.44
_cell_volume                     2828.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13133
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.196
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0807
_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)+(0.0196P)²+3.0292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                2018
_reflns_number_total             2720
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            aa2011.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C16 H17 N2 O1.50'
_cod_database_code               2231392
_cod_database_fobs_code          2231392
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.6204(2) 0.6782(2) 0.2566(2) 0.0725(8) Uani d . 1 1
H H1A 0.5851 0.6253 0.2539 0.087 Uiso calc R 1 1
C C2 0.6771(2) 0.6930(3) 0.1781(3) 0.0851(10) Uani d . 1 1
H H2A 0.6809 0.6497 0.1223 0.102 Uiso calc R 1 1
C C3 0.7285(2) 0.7711(3) 0.1814(3) 0.0863(11) Uani d . 1 1
H H3A 0.7671 0.7800 0.1274 0.104 Uiso calc R 1 1
C C4 0.72472(19) 0.8370(2) 0.2623(3) 0.0789(10) Uani d . 1 1
C C5 0.66713(18) 0.8218(2) 0.3437(3) 0.0699(8) Uani d . 1 1
H H5A 0.6636 0.8650 0.3996 0.084 Uiso calc R 1 1
C C6 0.61540(17) 0.7422(2) 0.3404(2) 0.0624(7) Uani d . 1 1
C C8 0.5560(2) 0.6505(2) 0.4939(2) 0.0681(8) Uani d . 1 1
C C9 0.6135(2) 0.5667(2) 0.4845(3) 0.0848(10) Uani d . 1 1
H H9A 0.6020 0.5215 0.5401 0.127 Uiso calc R 1 1
H H9B 0.6700 0.5884 0.4903 0.127 Uiso calc R 1 1
H H9C 0.6055 0.5361 0.4172 0.127 Uiso calc R 1 1
C C10 0.4610(2) 0.7482(2) 0.5473(2) 0.0681(8) Uani d . 1 1
C C11 0.3959(2) 0.7953(3) 0.5984(3) 0.0819(10) Uani d . 1 1
H H11A 0.3717 0.7687 0.6585 0.098 Uiso calc R 1 1
C C12 0.3683(2) 0.8807(3) 0.5596(3) 0.0756(9) Uani d . 1 1
H H12A 0.3245 0.9120 0.5932 0.091 Uiso calc R 1 1
C C13 0.40456(18) 0.9223(2) 0.4699(2) 0.0677(8) Uani d . 1 1
C C14 0.46999(17) 0.8783(2) 0.4176(2) 0.0611(7) Uani d . 1 1
H H14A 0.4946 0.9056 0.3583 0.073 Uiso calc R 1 1
C C15 0.49675(18) 0.7910(2) 0.4588(2) 0.0592(7) Uani d . 1 1
C C16 0.4029(2) 1.0538(3) 0.3480(3) 0.0863(10) Uani d . 1 1
H H16A 0.3731 1.1123 0.3341 0.129 Uiso calc R 1 1
H H16B 0.3979 1.0116 0.2883 0.129 Uiso calc R 1 1
H H16C 0.4605 1.0683 0.3601 0.129 Uiso calc R 1 1
N N1 0.55804(15) 0.72736(17) 0.42521(18) 0.0628(6) Uani d . 1 1
N N2 0.49971(19) 0.66035(18) 0.5677(2) 0.0764(7) Uani d . 1 1
O O1 0.36911(13) 1.00859(17) 0.43877(19) 0.0811(7) Uani d . 1 1
O O1W 0.5000 0.5327(2) 0.7500 0.0961(11) Uani d S 1 2
H H1W 0.4912 0.5668 0.6953 0.144 Uiso d R 1 1
C C7 0.7786(3) 0.9187(3) 0.2623(4) 0.1196(16) Uani d . 1 1
H H7A 0.8138 0.9166 0.2011 0.179 Uiso calc R 1 1
H H7B 0.8123 0.9180 0.3250 0.179 Uiso calc R 1 1
H H7C 0.7459 0.9764 0.2609 0.179 Uiso calc R 1 1
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
C2 C1 C6 119.9(3)
C2 C1 H1A 120.1
C6 C1 H1A 120.1
C1 C2 C3 120.2(4)
C1 C2 H2A 119.9
C3 C2 H2A 119.9
C2 C3 C4 121.7(3)
C2 C3 H3A 119.1
C4 C3 H3A 119.1
C3 C4 C5 118.4(3)
C3 C4 C7 120.2(4)
C5 C4 C7 121.4(4)
C6 C5 C4 119.7(3)
C6 C5 H5A 120.1
C4 C5 H5A 120.1
C5 C6 C1 120.1(3)
C5 C6 N1 118.8(3)
C1 C6 N1 121.2(3)
N2 C8 N1 112.6(3)
N2 C8 C9 124.6(3)
N1 C8 C9 122.8(3)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C15 C10 C11 118.8(3)
C15 C10 N2 109.8(3)
C11 C10 N2 131.4(3)
C12 C11 C10 119.2(3)
C12 C11 H11A 120.4
C10 C11 H11A 120.4
C11 C12 C13 121.2(3)
C11 C12 H12A 119.4
C13 C12 H12A 119.4
C14 C13 O1 124.1(3)
C14 C13 C12 121.3(3)
O1 C13 C12 114.7(3)
C13 C14 C15 116.3(3)
C13 C14 H14A 121.9
C15 C14 H14A 121.9
C14 C15 N1 131.4(3)
C14 C15 C10 123.2(3)
N1 C15 C10 105.4(3)
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C8 N1 C15 106.6(2)
C8 N1 C6 126.9(3)
C15 N1 C6 126.4(2)
C8 N2 C10 105.7(3)
C13 O1 C16 117.2(2)
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.363(5)
C1 C6 1.387(4)
C1 H1A 0.9300
C2 C3 1.366(5)
C2 H2A 0.9300
C3 C4 1.375(5)
C3 H3A 0.9300
C4 C5 1.400(4)
C4 C7 1.429(5)
C5 C6 1.385(4)
C5 H5A 0.9300
C6 N1 1.429(3)
C8 N2 1.307(4)
C8 N1 1.378(4)
C8 C9 1.492(4)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C15 1.392(4)
C10 C11 1.394(4)
C10 N2 1.395(4)
C11 C12 1.359(5)
C11 H11A 0.9300
C12 C13 1.401(4)
C12 H12A 0.9300
C13 C14 1.385(4)
C13 O1 1.386(4)
C14 C15 1.389(4)
C14 H14A 0.9300
C15 N1 1.391(4)
C16 O1 1.417(4)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
O1W H1W 0.8500
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 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
O1W H1W N2 0.85 2.08 2.911(3) 166.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656903
