#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/59/2225963.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_2225963
loop_
_publ_author_name
'Dong, Gui-Ying'
'Fan, Li-Hua'
'Yang, Li-Xia'
'Khan, Islam Ullah'
_publ_section_title
;
 Aqua(1H-benzimidazole-κN³)(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)copper(II)
 0.75-hydrate
;
_journal_coeditor_code           RK2200
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m532
_journal_paper_doi               10.1107/S160053681001353X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Cu (C7 H3 N O4) (C7 H6 N2) (H2 O)], 0.75H2 O'
_chemical_formula_moiety         'C14 H11 Cu N3 O5, 0.75(H2 O)'
_chemical_formula_sum            'C14 H12.5 Cu N3 O5.75'
_chemical_formula_weight         378.32
_chemical_name_systematic
;
Aqua(1H-benzimidazole-κN³)(pyridine-2,6-dicarboxylato-
κ³O²,N,O⁶)copper(II) 0.75-hydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6388(17)
_cell_length_b                   17.692(4)
_cell_length_c                   9.783(2)
_cell_measurement_reflns_used    2800
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.58
_cell_measurement_theta_min      4.36
_cell_volume                     1481.4(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12842
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.510
_exptl_absorpt_correction_T_max  0.759
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             770
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0489
_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)+(0.0321P)²+1.3817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2108
_reflns_number_total             2614
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2200.cif
_cod_data_source_block           I
_cod_original_cell_volume        1481.5(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C14 H12.5 Cu1 N3 O5.75 '
_cod_database_code               2225963
_cod_database_fobs_code          2225963
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cu Cu1 0.21983(5) 0.15993(3) 0.91593(5) 0.03235(18) Uani d . 1 . .
O O1W 0.1635(3) 0.14651(17) 1.1317(3) 0.0490(8) Uani d . 1 . .
H H1A 0.1016 0.1119 1.1510 0.074 Uiso d R 1 . .
H H1B 0.2504 0.1412 1.1831 0.074 Uiso d R 1 . .
O O1 0.2325(3) 0.04517(15) 0.8889(3) 0.0428(8) Uani d . 1 . .
O O2 0.0796(3) -0.05328(15) 0.8281(3) 0.0468(8) Uani d . 1 . .
O O3 -0.0676(3) 0.33244(15) 0.8066(3) 0.0379(7) Uani d . 1 . .
O O4 0.1407(3) 0.26612(14) 0.8944(3) 0.0348(7) Uani d . 1 . .
N N1 0.0128(3) 0.14008(17) 0.8315(3) 0.0272(7) Uani d . 1 . .
N N2 0.4407(4) 0.17683(17) 0.9703(3) 0.0325(8) Uani d . 1 . .
N N3 0.6752(4) 0.14636(19) 1.0717(4) 0.0381(9) Uani d . 1 . .
H H3A 0.7523 0.1188 1.1072 0.046 Uiso calc R 1 . .
C C1 0.1030(4) 0.0149(2) 0.8435(4) 0.0343(10) Uani d . 1 . .
C C2 -0.0305(4) 0.0691(2) 0.8052(4) 0.0290(9) Uani d . 1 . .
C C3 -0.1796(4) 0.0531(2) 0.7462(4) 0.0380(10) Uani d . 1 . .
H H3 -0.2121 0.0035 0.7291 0.046 Uiso calc R 1 . .
C C4 -0.2802(5) 0.1129(2) 0.7127(5) 0.0433(12) Uani d . 1 . .
H H4 -0.3820 0.1035 0.6720 0.052 Uiso calc R 1 . .
C C5 -0.2321(4) 0.1860(2) 0.7386(4) 0.0359(10) Uani d . 1 . .
H H5A -0.2998 0.2263 0.7154 0.043 Uiso calc R 1 . .
C C6 -0.0812(4) 0.1984(2) 0.7998(4) 0.0279(9) Uani d . 1 . .
C C7 0.0006(4) 0.2725(2) 0.8364(4) 0.0288(9) Uani d . 1 . .
C C8 0.5344(4) 0.1218(2) 1.0185(4) 0.0365(10) Uani d . 1 . .
H H8 0.5055 0.0712 1.0158 0.044 Uiso calc R 1 . .
C C9 0.6754(4) 0.2233(2) 1.0597(4) 0.0314(9) Uani d . 1 . .
C C10 0.7901(5) 0.2770(3) 1.1004(4) 0.0418(11) Uani d . 1 . .
H H10 0.8885 0.2636 1.1444 0.050 Uiso calc R 1 . .
C C11 0.7497(5) 0.3500(3) 1.0722(5) 0.0472(12) Uani d . 1 . .
H H11 0.8222 0.3878 1.0993 0.057 Uiso calc R 1 . .
C C12 0.6032(5) 0.3706(3) 1.0040(5) 0.0448(11) Uani d . 1 . .
H H12 0.5818 0.4213 0.9849 0.054 Uiso calc R 1 . .
C C13 0.4908(5) 0.3176(2) 0.9650(4) 0.0361(10) Uani d . 1 . .
H H13 0.3930 0.3315 0.9204 0.043 Uiso calc R 1 . .
C C14 0.5275(4) 0.2424(2) 0.9940(4) 0.0284(9) Uani d . 1 . .
O O2W 0.0560(6) 0.4772(2) 0.8653(7) 0.100(2) Uani d P 0.75 . .
H H2A 0.0357 0.4379 0.8162 0.150 Uiso d PR 0.75 . .
H H2B 0.0004 0.4956 0.9225 0.150 Uiso d PR 0.75 . .
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'
Cu Cu 0.3201 1.2651 '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
N1 Cu1 N2 . . 169.98(14) ?
N1 Cu1 O4 . . 80.76(12) ?
N2 Cu1 O4 . . 101.21(12) ?
N1 Cu1 O1 . . 79.88(12) ?
N2 Cu1 O1 . . 96.93(12) ?
O4 Cu1 O1 . . 159.86(10) ?
N1 Cu1 O1W . . 94.52(12) ?
N2 Cu1 O1W . . 95.10(13) ?
O4 Cu1 O1W . . 94.81(11) ?
O1 Cu1 O1W . . 92.20(12) ?
Cu1 O1W H1A . . 120.5 ?
Cu1 O1W H1B . . 106.3 ?
H1A O1W H1B . . 108.7 ?
C1 O1 Cu1 . . 113.8(2) ?
C7 O4 Cu1 . . 114.9(2) ?
C6 N1 C2 . . 123.0(3) ?
C6 N1 Cu1 . . 118.0(3) ?
C2 N1 Cu1 . . 119.0(3) ?
C8 N2 C14 . . 105.5(3) ?
C8 N2 Cu1 . . 121.5(3) ?
C14 N2 Cu1 . . 131.9(3) ?
C8 N3 C9 . . 107.7(3) ?
C8 N3 H3A . . 126.2 ?
C9 N3 H3A . . 126.2 ?
O2 C1 O1 . . 125.5(4) ?
O2 C1 C2 . . 119.1(3) ?
O1 C1 C2 . . 115.4(3) ?
N1 C2 C3 . . 120.2(4) ?
N1 C2 C1 . . 111.6(3) ?
C3 C2 C1 . . 128.2(4) ?
C2 C3 C4 . . 117.9(4) ?
C2 C3 H3 . . 121.1 ?
C4 C3 H3 . . 121.1 ?
C5 C4 C3 . . 120.9(4) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 118.4(4) ?
C4 C5 H5A . . 120.8 ?
C6 C5 H5A . . 120.8 ?
N1 C6 C5 . . 119.5(4) ?
N1 C6 C7 . . 111.7(3) ?
C5 C6 C7 . . 128.8(4) ?
O3 C7 O4 . . 125.4(4) ?
O3 C7 C6 . . 120.0(3) ?
O4 C7 C6 . . 114.6(3) ?
N2 C8 N3 . . 112.7(4) ?
N2 C8 H8 . . 123.7 ?
N3 C8 H8 . . 123.7 ?
N3 C9 C14 . . 105.7(3) ?
N3 C9 C10 . . 131.7(4) ?
C14 C9 C10 . . 122.7(4) ?
C11 C10 C9 . . 116.0(4) ?
C11 C10 H10 . . 122.0 ?
C9 C10 H10 . . 122.0 ?
C10 C11 C12 . . 122.4(4) ?
C10 C11 H11 . . 118.8 ?
C12 C11 H11 . . 118.8 ?
C13 C12 C11 . . 121.3(4) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C12 C13 C14 . . 117.8(4) ?
C12 C13 H13 . . 121.1 ?
C14 C13 H13 . . 121.1 ?
N2 C14 C9 . . 108.4(3) ?
N2 C14 C13 . . 131.8(4) ?
C9 C14 C13 . . 119.8(4) ?
H2A O2W H2B . . 126.4 ?
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
Cu1 N1 . 1.898(3) ?
Cu1 N2 . 1.934(3) ?
Cu1 O4 . 2.001(3) ?
Cu1 O1 . 2.052(3) ?
Cu1 O1W . 2.242(3) ?
O1W H1A . 0.8500 ?
O1W H1B . 0.8500 ?
O1 C1 . 1.265(4) ?
O2 C1 . 1.229(5) ?
O3 C7 . 1.229(4) ?
O4 C7 . 1.270(4) ?
N1 C6 . 1.324(5) ?
N1 C2 . 1.325(5) ?
N2 C8 . 1.312(5) ?
N2 C14 . 1.384(5) ?
N3 C8 . 1.329(5) ?
N3 C9 . 1.366(5) ?
N3 H3A . 0.8600 ?
C1 C2 . 1.507(5) ?
C2 C3 . 1.368(5) ?
C3 C4 . 1.380(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.372(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.509(5) ?
C8 H8 . 0.9300 ?
C9 C14 . 1.392(5) ?
C9 C10 . 1.391(5) ?
C10 C11 . 1.358(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.396(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.366(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.389(5) ?
C13 H13 . 0.9300 ?
O2W H2A . 0.8500 ?
O2W H2B . 0.8500 ?
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
O1W H1A O2 3_557 0.85 1.91 2.740(4) 164
O2W H2A O3 1_555 0.85 2.06 2.804(5) 145
O2W H2B O2w 3_567 0.85 2.25 3.037(9) 154
N3 H3A O2 3_657 0.86 1.90 2.756(4) 175
