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#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/78/2017800.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_2017800
loop_
_publ_author_name
'Xiao, Hailian'
'Wang, Guixue'
'Jian, Fangfang'
_publ_section_title
;
 Supramolecular interactions in the
 2,6-bis(benzimidazol-2-yl)pyridine--terephthalic acid--water (2/1/4)
 cocrystal
;
_journal_coeditor_code           EM3031
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o446
_journal_page_last               o448
_journal_paper_doi               10.1107/S0108270110025552
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H13 N5 , 0.5C8 H6 O4 , 2H2 O'
_chemical_formula_moiety         'C19 H13 N5 , 0.5C8 H6 O4 , 2H2 O'
_chemical_formula_sum            'C23 H20 N5 O4'
_chemical_formula_weight         430.44
_chemical_name_systematic
;
2,6-bis(benzimidazol-2-yl)pyridine--terephthalic acid--water (2/1/4)
;
_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           SHELXL97
_cell_angle_alpha                80.19(3)
_cell_angle_beta                 81.13(3)
_cell_angle_gamma                74.88(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5040(19)
_cell_length_b                   9.888(2)
_cell_length_c                   11.713(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     1040.1(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXL (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3660
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0531
_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)+(0.0819P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                1926
_reflns_number_total             3660
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            em3031.cif
_cod_data_source_block           I
_cod_original_cell_volume        1040.1(3)
_cod_database_code               2017800
_cod_database_fobs_code          2017800
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
N N1 0.1641(2) 0.8680(3) 0.1945(2) 0.0591(7) Uani d . 1 . .
H H1 0.2028 0.8023 0.1516 0.071 Uiso d R 1 . .
N N2 -0.0078(2) 1.0315(3) 0.2810(2) 0.0585(7) Uani d . 1 . .
N N3 -0.0278(2) 0.8192(3) 0.0638(2) 0.0528(7) Uani d . 1 . .
N N4 -0.1258(2) 0.6490(3) -0.1512(2) 0.0592(7) Uani d . 1 . .
N N5 0.0903(2) 0.6236(3) -0.0879(2) 0.0558(7) Uani d . 1 . .
H H5 0.1540 0.6361 -0.0485 0.067 Uiso d R 1 . .
C C1 0.2364(3) 0.9215(4) 0.2658(3) 0.0577(8) Uani d . 1 . .
C C2 0.3815(3) 0.8940(4) 0.2815(3) 0.0699(10) Uani d . 1 . .
H H2A 0.4524 0.8256 0.2451 0.084 Uiso calc R 1 . .
C C3 0.4170(4) 0.9729(5) 0.3540(3) 0.0861(13) Uani d . 1 . .
H H3 0.5144 0.9582 0.3666 0.103 Uiso calc R 1 . .
C C4 0.3089(4) 1.0754(5) 0.4095(3) 0.0842(12) Uani d . 1 . .
H H4 0.3358 1.1278 0.4576 0.101 Uiso calc R 1 . .
C C5 0.1648(3) 1.0987(4) 0.3933(3) 0.0709(10) Uani d . 1 . .
H H5A 0.0929 1.1648 0.4313 0.085 Uiso calc R 1 . .
C C6 0.1284(3) 1.0220(4) 0.3191(3) 0.0594(9) Uani d . 1 . .
C C7 0.0218(3) 0.9389(3) 0.2065(2) 0.0540(8) Uani d . 1 . .
C C8 -0.0829(3) 0.9177(4) 0.1366(2) 0.0534(8) Uani d . 1 . .
C C9 -0.2281(3) 0.9958(3) 0.1418(3) 0.0599(9) Uani d . 1 . .
H H9 -0.2634 1.0634 0.1923 0.072 Uiso calc R 1 . .
C C10 -0.3174(3) 0.9708(4) 0.0708(3) 0.0679(10) Uani d . 1 . .
H H10 -0.4147 1.0218 0.0726 0.081 Uiso calc R 1 . .
C C11 -0.2645(3) 0.8716(4) -0.0024(3) 0.0602(9) Uani d . 1 . .
H H11 -0.3247 0.8541 -0.0509 0.072 Uiso calc R 1 . .
C C12 -0.1198(3) 0.7975(3) -0.0035(2) 0.0506(8) Uani d . 1 . .
C C13 -0.0546(3) 0.6907(3) -0.0812(2) 0.0517(8) Uani d . 1 . .
C C14 -0.0198(3) 0.5495(3) -0.2093(2) 0.0549(8) Uani d . 1 . .
C C15 -0.0325(3) 0.4745(4) -0.2952(3) 0.0691(10) Uani d . 1 . .
H H15 -0.1223 0.4863 -0.3225 0.083 Uiso calc R 1 . .
C C16 0.0900(4) 0.3825(4) -0.3388(3) 0.0756(11) Uani d . 1 . .
H H16 0.0836 0.3317 -0.3969 0.091 Uiso calc R 1 . .
C C17 0.2262(3) 0.3638(4) -0.2967(3) 0.0746(10) Uani d . 1 . .
H H17 0.3080 0.2998 -0.3270 0.090 Uiso calc R 1 . .
C C18 0.2402(3) 0.4384(4) -0.2115(3) 0.0650(9) Uani d . 1 . .
H H18 0.3298 0.4261 -0.1836 0.078 Uiso calc R 1 . .
C C19 0.1163(3) 0.5318(3) -0.1696(2) 0.0550(8) Uani d . 1 . .
O O1 0.6153(2) 0.2410(3) 0.2946(2) 0.0892(9) Uani d . 1 . .
O O2 0.7970(2) 0.2170(3) 0.40003(18) 0.0715(7) Uani d . 1 . .
H H2 0.8460 0.1739 0.3476 0.107 Uiso d R 1 . .
C C20 0.4424(3) 0.4649(4) 0.4124(3) 0.0666(10) Uani d . 1 . .
H H20 0.4035 0.4414 0.3523 0.080 Uiso calc R 1 . .
C C21 0.5803(3) 0.3894(3) 0.4407(2) 0.0538(8) Uani d . 1 . .
C C22 0.6370(3) 0.4268(4) 0.5284(3) 0.0636(9) Uani d . 1 . .
H H22 0.7300 0.3782 0.5476 0.076 Uiso calc R 1 . .
C C23 0.6644(3) 0.2755(4) 0.3714(3) 0.0595(9) Uani d . 1 . .
O O1W 0.4218(2) 0.3516(3) 0.1293(2) 0.0794(8) Uani d D 1 . .
H H1W 0.337(2) 0.341(5) 0.145(3) 0.119 Uiso d D 1 . .
H H2W 0.468(3) 0.319(5) 0.187(2) 0.119 Uiso d D 1 . .
O O2W 0.3381(2) 0.6469(4) 0.0495(3) 0.0884(8) Uani d D 1 . .
H H3W 0.410(4) 0.658(5) 0.087(3) 0.133 Uiso d D 1 . .
H H4W 0.392(5) 0.645(8) -0.019(2) 0.133 Uiso d PD 0.55(6) A 1
H H5W 0.350(8) 0.556(3) 0.074(6) 0.133 Uiso d PD 0.45(6) A 2
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
C7 N1 C1 . . 106.9(2) ?
C7 N1 H1 . . 126.5 ?
C1 N1 H1 . . 126.6 ?
C7 N2 C6 . . 104.5(2) ?
C12 N3 C8 . . 117.2(2) ?
C13 N4 C14 . . 105.0(2) ?
C13 N5 C19 . . 107.4(2) ?
C13 N5 H5 . . 126.3 ?
C19 N5 H5 . . 126.3 ?
C2 C1 C6 . . 123.1(3) ?
C2 C1 N1 . . 131.6(3) ?
C6 C1 N1 . . 105.2(2) ?
C1 C2 C3 . . 116.5(3) ?
C1 C2 H2A . . 121.7 ?
C3 C2 H2A . . 121.7 ?
C2 C3 C4 . . 121.4(3) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 120.6(3) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 118.5(3) ?
C4 C5 H5A . . 120.8 ?
C6 C5 H5A . . 120.8 ?
C5 C6 C1 . . 119.9(3) ?
C5 C6 N2 . . 130.1(3) ?
C1 C6 N2 . . 109.9(3) ?
N2 C7 N1 . . 113.4(2) ?
N2 C7 C8 . . 125.1(2) ?
N1 C7 C8 . . 121.3(3) ?
N3 C8 C9 . . 122.4(3) ?
N3 C8 C7 . . 115.1(2) ?
C9 C8 C7 . . 122.5(3) ?
C10 C9 C8 . . 118.3(3) ?
C10 C9 H9 . . 120.8 ?
C8 C9 H9 . . 120.8 ?
C11 C10 C9 . . 120.3(3) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 118.7(3) ?
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
N3 C12 C11 . . 123.2(3) ?
N3 C12 C13 . . 115.0(2) ?
C11 C12 C13 . . 121.8(3) ?
N4 C13 N5 . . 112.8(3) ?
N4 C13 C12 . . 125.2(2) ?
N5 C13 C12 . . 122.0(2) ?
C15 C14 N4 . . 129.9(3) ?
C15 C14 C19 . . 120.3(3) ?
N4 C14 C19 . . 109.8(3) ?
C16 C15 C14 . . 118.5(3) ?
C16 C15 H15 . . 120.8 ?
C14 C15 H15 . . 120.8 ?
C15 C16 C17 . . 120.8(3) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C18 C17 C16 . . 121.3(3) ?
C18 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C19 C18 C17 . . 117.2(3) ?
C19 C18 H18 . . 121.4 ?
C17 C18 H18 . . 121.4 ?
C18 C19 N5 . . 133.0(3) ?
C18 C19 C14 . . 122.0(3) ?
N5 C19 C14 . . 105.0(2) ?
C23 O2 H2 . . 109.5 ?
C22 C20 C21 2_666 . 120.8(3) ?
C22 C20 H20 2_666 . 119.6 ?
C21 C20 H20 . . 119.6 ?
C22 C21 C20 . . 118.8(3) ?
C22 C21 C23 . . 122.2(2) ?
C20 C21 C23 . . 118.9(3) ?
C20 C22 C21 2_666 . 120.4(3) ?
C20 C22 H22 2_666 . 119.8 ?
C21 C22 H22 . . 119.8 ?
O1 C23 O2 . . 123.0(3) ?
O1 C23 C21 . . 122.9(3) ?
O2 C23 C21 . . 114.1(3) ?
H1W O1W H2W . . 110(3) ?
H3W O2W H4W . . 94(2) ?
H3W O2W H5W . . 95(2) ?
H4W O2W H5W . . 100(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
N1 C7 . 1.349(3) y
N1 C1 . 1.402(4) y
N1 H1 . 0.8599 ?
N2 C7 . 1.320(4) y
N2 C6 . 1.408(3) y
N3 C12 . 1.342(3) y
N3 C8 . 1.352(4) y
N4 C13 . 1.316(4) y
N4 C14 . 1.395(4) y
N5 C13 . 1.361(3) y
N5 C19 . 1.381(4) y
N5 H5 . 0.8599 ?
C1 C2 . 1.370(4) ?
C1 C6 . 1.383(4) ?
C2 C3 . 1.376(5) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.407(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.366(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(4) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.457(4) ?
C8 C9 . 1.392(4) ?
C9 C10 . 1.368(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.359(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.463(4) ?
C14 C15 . 1.384(4) ?
C14 C19 . 1.399(4) ?
C15 C16 . 1.366(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.411(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.379(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.375(4) ?
C18 H18 . 0.9300 ?
O1 C23 . 1.209(3) ?
O2 C23 . 1.311(3) ?
O2 H2 . 0.8202 ?
C20 C22 2_666 1.367(4) ?
C20 C21 . 1.387(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.374(4) ?
C21 C23 . 1.486(4) ?
C22 C20 2_666 1.367(4) ?
C22 H22 . 0.9300 ?
O1W H1W . 0.824(18) ?
O1W H2W . 0.838(18) ?
O2W H3W . 0.911(18) ?
O2W H4W . 0.88(2) ?
O2W H5W . 0.87(2) ?
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
_geom_hbond_publ_flag
N1 H1 O2W . 0.86 2.14 2.985(4) 168.9 y
N5 H5 O2W . 0.86 2.27 3.125(4) 173.8 y
O2 H2 N2 1_645 0.82 1.88 2.655(3) 156.6 y
O1W H1W N4 2_565 0.824(18) 1.979(18) 2.787(3) 167(4) y
O1W H2W O1 . 0.838(18) 1.944(18) 2.766(3) 167(4) y
O2W H5W O1W . 0.87(2) 1.99(3) 2.849(5) 168(6) y
O2W H4W O1W 2_665 0.88(2) 2.03(3) 2.850(4) 155(5) y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . -175.6(4) ?
C7 N1 C1 C6 . . . . 1.2(3) ?
C6 C1 C2 C3 . . . . -0.3(5) ?
N1 C1 C2 C3 . . . . 176.0(3) ?
C1 C2 C3 C4 . . . . 0.5(6) ?
C2 C3 C4 C5 . . . . 0.4(6) ?
C3 C4 C5 C6 . . . . -1.6(6) ?
C4 C5 C6 C1 . . . . 1.8(5) ?
C4 C5 C6 N2 . . . . -175.2(3) ?
C2 C1 C6 C5 . . . . -0.8(5) ?
N1 C1 C6 C5 . . . . -178.0(3) ?
C2 C1 C6 N2 . . . . 176.7(3) ?
N1 C1 C6 N2 . . . . -0.5(4) ?
C7 N2 C6 C5 . . . . 176.7(4) ?
C7 N2 C6 C1 . . . . -0.4(4) ?
C6 N2 C7 N1 . . . . 1.3(4) ?
C6 N2 C7 C8 . . . . -175.0(3) ?
C1 N1 C7 N2 . . . . -1.6(4) ?
C1 N1 C7 C8 . . . . 174.8(3) ?
C12 N3 C8 C9 . . . . -0.9(5) ?
C12 N3 C8 C7 . . . . -179.1(3) ?
N2 C7 C8 N3 . . . . 178.4(3) ?
N1 C7 C8 N3 . . . . 2.4(4) ?
N2 C7 C8 C9 . . . . 0.2(5) ?
N1 C7 C8 C9 . . . . -175.8(3) ?
N3 C8 C9 C10 . . . . 0.4(5) ?
C7 C8 C9 C10 . . . . 178.5(3) ?
C8 C9 C10 C11 . . . . 0.1(5) ?
C9 C10 C11 C12 . . . . 0.0(5) ?
C8 N3 C12 C11 . . . . 1.0(5) ?
C8 N3 C12 C13 . . . . 179.6(3) ?
C10 C11 C12 N3 . . . . -0.5(5) ?
C10 C11 C12 C13 . . . . -179.1(3) ?
C14 N4 C13 N5 . . . . -1.1(4) ?
C14 N4 C13 C12 . . . . 178.8(3) ?
C19 N5 C13 N4 . . . . 0.7(4) ?
C19 N5 C13 C12 . . . . -179.2(3) ?
N3 C12 C13 N4 . . . . 177.3(3) ?
C11 C12 C13 N4 . . . . -4.0(5) ?
N3 C12 C13 N5 . . . . -2.8(4) ?
C11 C12 C13 N5 . . . . 175.8(3) ?
C13 N4 C14 C15 . . . . -178.0(4) ?
C13 N4 C14 C19 . . . . 1.1(4) ?
N4 C14 C15 C16 . . . . 179.7(3) ?
C19 C14 C15 C16 . . . . 0.6(5) ?
C14 C15 C16 C17 . . . . 0.4(6) ?
C15 C16 C17 C18 . . . . -0.7(6) ?
C16 C17 C18 C19 . . . . -0.1(5) ?
C17 C18 C19 N5 . . . . -178.8(4) ?
C17 C18 C19 C14 . . . . 1.2(5) ?
C13 N5 C19 C18 . . . . -180.0(4) ?
C13 N5 C19 C14 . . . . 0.1(3) ?
C15 C14 C19 C18 . . . . -1.5(5) ?
N4 C14 C19 C18 . . . . 179.3(3) ?
C15 C14 C19 N5 . . . . 178.5(3) ?
N4 C14 C19 N5 . . . . -0.7(4) ?
C22 C20 C21 C22 2_666 . . . -1.0(6) ?
C22 C20 C21 C23 2_666 . . . -178.1(3) ?
C20 C21 C22 C20 . . . 2_666 1.0(6) ?
C23 C21 C22 C20 . . . 2_666 178.0(3) ?
C22 C21 C23 O1 . . . . 179.5(4) ?
C20 C21 C23 O1 . . . . -3.5(5) ?
C22 C21 C23 O2 . . . . -1.3(5) ?
C20 C21 C23 O2 . . . . 175.7(3) ?
