#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227400.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_2227400
loop_
_publ_author_name
'Gupta, Parna'
'Mandal, Soumik'
_publ_section_title
;
 Methyl 4-(1H-benzimidazol-2-yl)benzoate trihydrate
;
_journal_coeditor_code           DS2060
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2754
_journal_paper_doi               10.1107/S1600536810039188
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H12 N2 O2, 3H2 O'
_chemical_formula_moiety         'C15 H12 N2 O2, 3(H2 O)'
_chemical_formula_sum            'C15 H18 N2 O5'
_chemical_formula_weight         306.32
_chemical_name_systematic
;
Methyl 4-(1H-benzimidazol-2-yl)benzoate trihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.718(3)
_cell_angle_beta                 101.718(4)
_cell_angle_gamma                97.621(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8308(3)
_cell_length_b                   10.8165(5)
_cell_length_c                   11.5254(8)
_cell_measurement_reflns_used    8743
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      40.67
_cell_measurement_theta_min      2.17
_cell_volume                     734.41(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10457
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.409
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0423
_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)+(0.1051P)²+0.1366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                2873
_reflns_number_total             3194
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2060.cif
_cod_data_source_block           I
_cod_database_code               2227400
_cod_database_fobs_code          2227400
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.31311(14) 0.28296(9) 0.39119(8) 0.0166(2) Uani d . 1 . .
O O5 0.21253(15) 0.02407(10) 0.63276(9) 0.0209(2) Uani d . 1 . .
H H21 0.155(3) -0.050(2) 0.554(2) 0.031 Uiso d . 1 . .
H H20 0.122(3) 0.076(2) 0.6355(19) 0.031 Uiso d . 1 . .
O O3 0.37646(14) 0.87010(9) 0.26610(9) 0.0176(2) Uani d . 1 . .
H H17 0.523(3) 0.9011(18) 0.3003(17) 0.026 Uiso d . 1 . .
H H16 0.333(3) 0.9357(19) 0.2506(17) 0.026 Uiso d . 1 . .
O O2 0.22975(14) 0.07258(9) 0.20910(9) 0.0182(2) Uani d . 1 . .
O O4 0.07060(15) 0.80876(9) 0.37434(9) 0.0207(2) Uani d . 1 . .
H H19 -0.003(3) 0.723(2) 0.3151(19) 0.031 Uiso d . 1 . .
H H18 0.170(3) 0.8188(19) 0.3397(19) 0.031 Uiso d . 1 . .
N N1 0.19210(15) 0.44471(10) -0.18336(10) 0.0133(2) Uani d . 1 . .
N N2 0.28539(14) 0.64581(10) 0.00717(9) 0.0124(2) Uani d . 1 . .
H H2 0.3197 0.7017 0.0912 0.015 Uiso calc R 1 . .
C C1 0.3320(2) 0.21255(13) 0.47386(13) 0.0211(3) Uani d . 1 . .
H H1A 0.2092 0.1397 0.4436 0.032 Uiso calc R 1 . .
H H1B 0.3504 0.2790 0.5647 0.032 Uiso calc R 1 . .
H H1C 0.4488 0.1722 0.4682 0.032 Uiso calc R 1 . .
C C2 0.26140(17) 0.20014(12) 0.25945(12) 0.0135(3) Uani d . 1 . .
C C3 0.24921(17) 0.28025(12) 0.18125(11) 0.0127(3) Uani d . 1 . .
C C4 0.29491(18) 0.42689(12) 0.24419(12) 0.0146(3) Uani d . 1 . .
H H4 0.3289 0.4763 0.3366 0.018 Uiso calc R 1 . .
C C5 0.28948(18) 0.49866(12) 0.16823(12) 0.0146(3) Uani d . 1 . .
H H5 0.3193 0.5962 0.2104 0.017 Uiso calc R 1 . .
C C6 0.23967(17) 0.42582(11) 0.02890(11) 0.0121(3) Uani d . 1 . .
C C7 0.23803(17) 0.50275(12) -0.05091(12) 0.0120(2) Uani d . 1 . .
C C8 0.21047(17) 0.55767(12) -0.21278(11) 0.0130(3) Uani d . 1 . .
C C9 0.17985(19) 0.56017(13) -0.33573(12) 0.0166(3) Uani d . 1 . .
H H9 0.1431 0.4777 -0.4155 0.020 Uiso calc R 1 . .
C C10 0.20643(19) 0.69051(13) -0.33395(12) 0.0179(3) Uani d . 1 . .
H H10 0.1872 0.6949 -0.4142 0.021 Uiso calc R 1 . .
C C11 0.19577(18) 0.20677(12) 0.04230(12) 0.0150(3) Uani d . 1 . .
H H11 0.1628 0.1092 0.0003 0.018 Uiso calc R 1 . .
C C12 0.19151(18) 0.27840(12) -0.03356(12) 0.0147(3) Uani d . 1 . .
H H12 0.1567 0.2286 -0.1260 0.018 Uiso calc R 1 . .
C C13 0.26809(17) 0.68429(12) -0.09392(11) 0.0124(3) Uani d . 1 . .
C C14 0.29457(18) 0.81564(12) -0.09143(12) 0.0155(3) Uani d . 1 . .
H H14 0.3323 0.8983 -0.0118 0.019 Uiso calc R 1 . .
C C15 0.26175(18) 0.81641(13) -0.21382(13) 0.0170(3) Uani d . 1 . .
H H15 0.2765 0.9017 -0.2167 0.020 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C1 . . 116.02(9) ?
H21 O5 H20 . . 101.8(17) ?
H17 O3 H16 . . 107.0(16) ?
H19 O4 H18 . . 101.0(17) ?
C7 N1 C8 . . 104.98(9) ?
C7 N2 C13 . . 107.37(9) ?
C7 N2 H2 . . 126.3 ?
C13 N2 H2 . . 126.3 ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C2 O1 . . 123.50(11) ?
O2 C2 C3 . . 123.61(11) ?
O1 C2 C3 . . 112.89(10) ?
C11 C3 C4 . . 119.73(10) ?
C11 C3 C2 . . 118.94(10) ?
C4 C3 C2 . . 121.31(11) ?
C5 C4 C3 . . 119.82(11) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.82(11) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C12 . . 118.95(10) ?
C5 C6 C7 . . 120.52(10) ?
C12 C6 C7 . . 120.53(10) ?
N1 C7 N2 . . 112.56(10) ?
N1 C7 C6 . . 125.68(10) ?
N2 C7 C6 . . 121.76(10) ?
N1 C8 C9 . . 130.49(11) ?
N1 C8 C13 . . 109.61(10) ?
C9 C8 C13 . . 119.89(10) ?
C10 C9 C8 . . 117.47(11) ?
C10 C9 H9 . . 121.3 ?
C8 C9 H9 . . 121.3 ?
C9 C10 C15 . . 121.84(11) ?
C9 C10 H10 . . 119.1 ?
C15 C10 H10 . . 119.1 ?
C12 C11 C3 . . 120.47(11) ?
C12 C11 H11 . . 119.8 ?
C3 C11 H11 . . 119.8 ?
C11 C12 C6 . . 120.20(11) ?
C11 C12 H12 . . 119.9 ?
C6 C12 H12 . . 119.9 ?
N2 C13 C14 . . 131.59(11) ?
N2 C13 C8 . . 105.47(10) ?
C14 C13 C8 . . 122.93(11) ?
C15 C14 C13 . . 116.52(11) ?
C15 C14 H14 . . 121.7 ?
C13 C14 H14 . . 121.7 ?
C14 C15 C10 . . 121.34(11) ?
C14 C15 H15 . . 119.3 ?
C10 C15 H15 . . 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.3391(14) ?
O1 C1 . 1.4448(14) ?
O5 H21 . 0.88(2) ?
O5 H20 . 0.88(2) ?
O3 H17 . 0.952(19) ?
O3 H16 . 0.875(19) ?
O2 C2 . 1.2197(14) ?
O4 H19 . 0.88(2) ?
O4 H18 . 0.87(2) ?
N1 C7 . 1.3321(15) ?
N1 C8 . 1.3953(14) ?
N2 C7 . 1.3638(14) ?
N2 C13 . 1.3810(14) ?
N2 H2 . 0.8600 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.4873(15) ?
C3 C11 . 1.3966(16) ?
C3 C4 . 1.3978(16) ?
C4 C5 . 1.3904(16) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.4015(16) ?
C5 H5 . 0.9300 ?
C6 C12 . 1.4049(16) ?
C6 C7 . 1.4754(15) ?
C8 C9 . 1.4021(16) ?
C8 C13 . 1.4058(16) ?
C9 C10 . 1.3882(16) ?
C9 H9 . 0.9300 ?
C10 C15 . 1.4102(18) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.3885(16) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.3956(15) ?
C14 C15 . 1.3864(17) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2 O3 1 0.86 1.99 2.8230(13) 163.3
O4 H18 O3 1 0.87(2) 1.92(2) 2.7830(13) 170.1(17)
O3 H16 O2 1_565 0.875(19) 1.910(19) 2.7840(12) 177.4(17)
O3 H17 O5 2_666 0.952(19) 1.745(19) 2.6932(13) 173.9(16)
O4 H19 N1 2_565 0.88(2) 1.89(2) 2.7614(14) 171.0(18)
O5 H20 O4 2_566 0.88(2) 1.95(2) 2.8291(14) 174.0(18)
O5 H21 O4 1_545 0.88(2) 1.90(2) 2.7679(13) 168.7(18)
C15 H15 O5 1_564 0.93 2.59 3.4009(15) 145.7
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656214
