#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/87/2018716.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_2018716
loop_
_publ_author_name
'Wang, Xiao-Dan'
'Hou, Guang-Feng'
'Yu, Ying-Hui'
'Gao, Jin-Sheng'
_publ_section_title
;
 catena-Poly[[nickel(II)-μ₂-[1,3-bis(imidazol-1-ylmethyl)benzene-κ²N³:N^3'^]-μ₂-(5-carboxybenzene-1,3-dicarboxylato-κ⁴O¹,O^1'^:O³,O^3'^)]
 0.41-hydrate]
;
_journal_coeditor_code           FN3119
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m336
_journal_page_last               m339
_journal_paper_doi               10.1107/S0108270112044393
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ni (C9 H4 O6) (C14 H14 N4)] , 0.41H2 O'
_chemical_formula_moiety         'C23 H18 N4 Ni O6, 0.41(H2 O)'
_chemical_formula_sum            'C23 H18.82 N4 Ni O6.41'
_chemical_formula_weight         512.49
_chemical_name_systematic
;
catena-Poly[[nickel(II)-μ₂-[1,3-bis(imidazol-1-ylmethyl)benzene-
κ²N³:N^3'^]-μ₂-(5-carboxybenzene-1,3-dicarboxylato-
κ⁴O¹,O^1'^:O³,O^3'^)] 0.41-hydrate]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8106(16)
_cell_length_b                   16.929(3)
_cell_length_c                   17.144(5)
_cell_measurement_reflns_used    16428
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      3.13
_cell_volume                     2184.6(9)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20085
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.8178
_exptl_absorpt_correction_T_min  0.7716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0440P)²+0.5113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                3999
_reflns_number_total             4929
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3119.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018716
_cod_database_fobs_code          2018716
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
C C1 0.0868(3) 0.98611(13) 0.23406(13) 0.0356(5) Uani d . 1 1
H H1 0.1952 0.9988 0.2244 0.043 Uiso calc R 1 1
C C2 -0.0295(3) 1.03873(13) 0.25062(13) 0.0370(5) Uani d . 1 1
H H2 -0.0162 1.0933 0.2545 0.044 Uiso calc R 1 1
C C3 -0.1352(3) 0.91945(12) 0.25001(13) 0.0330(4) Uani d . 1 1
H H3 -0.2104 0.8779 0.2538 0.040 Uiso calc R 1 1
C C4 -0.3254(3) 1.02498(13) 0.28569(13) 0.0372(5) Uani d . 1 1
H H4A -0.4318 0.9981 0.2550 0.045 Uiso calc R 1 1
H H4B -0.3403 1.0810 0.2742 0.045 Uiso calc R 1 1
C C5 -0.3010(3) 1.01105(12) 0.37488(13) 0.0328(4) Uani d . 1 1
C C6 -0.2167(3) 1.06650(13) 0.43240(14) 0.0401(5) Uani d . 1 1
H H6 -0.1778 1.1140 0.4160 0.048 Uiso calc R 1 1
C C7 -0.1908(3) 1.05096(15) 0.51355(15) 0.0467(6) Uani d . 1 1
H H7 -0.1355 1.0884 0.5517 0.056 Uiso calc R 1 1
C C8 -0.2466(3) 0.98011(15) 0.53886(14) 0.0435(5) Uani d . 1 1
H H8 -0.2280 0.9702 0.5938 0.052 Uiso calc R 1 1
C C9 -0.3299(3) 0.92409(13) 0.48280(13) 0.0363(5) Uani d . 1 1
C C10 -0.3572(3) 0.94042(13) 0.40075(13) 0.0355(5) Uani d . 1 1
H H10 -0.4142 0.9033 0.3626 0.043 Uiso calc R 1 1
C C11 -0.3986(3) 0.84580(15) 0.50568(16) 0.0475(6) Uani d . 1 1
H H11A -0.5228 0.8520 0.5044 0.057 Uiso calc R 1 1
H H11B -0.3917 0.8067 0.4653 0.057 Uiso calc R 1 1
C C12 -0.3550(3) 0.81812(15) 0.65550(16) 0.0479(6) Uani d . 1 1
H H12 -0.4594 0.8399 0.6623 0.058 Uiso calc R 1 1
C C13 -0.2267(3) 0.78261(13) 0.71262(15) 0.0415(5) Uani d . 1 1
H H13 -0.2280 0.7755 0.7662 0.050 Uiso calc R 1 1
C C14 -0.1445(3) 0.77928(13) 0.60296(13) 0.0337(4) Uani d . 1 1
H H14 -0.0797 0.7698 0.5656 0.040 Uiso calc R 1 1
C C15 0.3727(2) 0.67887(11) 0.41504(11) 0.0271(4) Uani d . 1 1
C C16 0.3100(3) 0.68329(11) 0.48368(12) 0.0293(4) Uani d . 1 1
H H16 0.2089 0.7130 0.4821 0.035 Uiso calc R 1 1
C C17 0.3953(3) 0.64435(11) 0.55408(11) 0.0282(4) Uani d . 1 1
C C18 0.5481(3) 0.60083(12) 0.55714(11) 0.0301(4) Uani d . 1 1
H H18 0.6063 0.5743 0.6043 0.036 Uiso calc R 1 1
C C19 0.6134(3) 0.59721(12) 0.48901(12) 0.0301(4) Uani d . 1 1
C C20 0.5256(3) 0.63564(12) 0.41807(11) 0.0297(4) Uani d . 1 1
H H20 0.5690 0.6325 0.3727 0.036 Uiso calc R 1 1
C C21 0.2826(3) 0.72423(12) 0.34093(12) 0.0284(4) Uani d . 1 1
C C22 0.3235(3) 0.65098(12) 0.62762(11) 0.0294(4) Uani d . 1 1
C C23 0.7821(3) 0.55387(13) 0.49284(12) 0.0357(5) Uani d . 1 1
N N1 0.0193(2) 0.91090(10) 0.23369(10) 0.0304(4) Uani d . 1 1
N N2 -0.1705(2) 0.99559(10) 0.26044(10) 0.0316(4) Uani d . 1 1
N N3 -0.0922(2) 0.75817(10) 0.67968(10) 0.0317(4) Uani d . 1 1
N N4 -0.3029(2) 0.81615(11) 0.58500(12) 0.0397(4) Uani d . 1 1
Ni Ni1 0.13384(3) 0.805870(14) 0.224375(14) 0.02599(9) Uani d . 1 1
O O1 0.3176(2) 0.71167(9) 0.27453(8) 0.0349(3) Uani d . 1 1
O O2 0.1706(2) 0.77737(10) 0.34571(9) 0.0420(4) Uani d . 1 1
O O3 0.1779(2) 0.68850(9) 0.61615(9) 0.0399(4) Uani d . 1 1
O O4 0.4030(2) 0.62242(10) 0.69351(9) 0.0413(4) Uani d . 1 1
O O5 0.8556(2) 0.56209(13) 0.43742(10) 0.0645(6) Uani d . 1 1
O O6 0.8409(2) 0.51034(11) 0.55490(10) 0.0484(4) Uani d D 1 1
H H61 0.939(3) 0.489(2) 0.553(3) 0.136(17) Uiso d D 1 1
O O7 0.8747(6) 0.7522(3) 0.4139(3) 0.069(2) Uani d PU 0.415(7) 1
H H71 0.8488 0.7034 0.4079 0.103 Uiso d PR 0.415(7) 1
H H72 0.9492 0.7622 0.3870 0.103 Uiso d PR 0.415(7) 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'
Ni Ni 0.3393 1.1124 '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
C2 C1 N1 . . 109.39(18)
C2 C1 H1 . . 125.3
N1 C1 H1 . . 125.3
C1 C2 N2 . . 106.34(19)
C1 C2 H2 . . 126.8
N2 C2 H2 . . 126.8
N1 C3 N2 . . 111.52(18)
N1 C3 H3 . . 124.2
N2 C3 H3 . . 124.2
N2 C4 C5 . . 110.68(17)
N2 C4 H4A . . 109.5
C5 C4 H4A . . 109.5
N2 C4 H4B . . 109.5
C5 C4 H4B . . 109.5
H4A C4 H4B . . 108.1
C10 C5 C6 . . 119.0(2)
C10 C5 C4 . . 119.60(19)
C6 C5 C4 . . 121.3(2)
C7 C6 C5 . . 120.0(2)
C7 C6 H6 . . 120.0
C5 C6 H6 . . 120.0
C6 C7 C8 . . 120.6(2)
C6 C7 H7 . . 119.7
C8 C7 H7 . . 119.7
C9 C8 C7 . . 120.3(2)
C9 C8 H8 . . 119.8
C7 C8 H8 . . 119.8
C8 C9 C10 . . 118.9(2)
C8 C9 C11 . . 123.5(2)
C10 C9 C11 . . 117.7(2)
C5 C10 C9 . . 121.2(2)
C5 C10 H10 . . 119.4
C9 C10 H10 . . 119.4
N4 C11 C9 . . 114.4(2)
N4 C11 H11A . . 108.7
C9 C11 H11A . . 108.7
N4 C11 H11B . . 108.7
C9 C11 H11B . . 108.7
H11A C11 H11B . . 107.6
C13 C12 N4 . . 106.96(19)
C13 C12 H12 . . 126.5
N4 C12 H12 . . 126.5
C12 C13 N3 . . 109.7(2)
C12 C13 H13 . . 125.2
N3 C13 H13 . . 125.2
N3 C14 N4 . . 112.05(17)
N3 C14 H14 . . 124.0
N4 C14 H14 . . 124.0
C20 C15 C16 . . 119.29(18)
C20 C15 C21 . . 120.58(16)
C16 C15 C21 . . 120.02(17)
C17 C16 C15 . . 121.13(17)
C17 C16 H16 . . 119.4
C15 C16 H16 . . 119.4
C16 C17 C18 . . 119.64(17)
C16 C17 C22 . . 119.53(17)
C18 C17 C22 . . 120.82(18)
C17 C18 C19 . . 119.56(18)
C17 C18 H18 . . 120.2
C19 C18 H18 . . 120.2
C20 C19 C18 . . 120.49(17)
C20 C19 C23 . . 119.48(17)
C18 C19 C23 . . 120.00(18)
C19 C20 C15 . . 119.88(17)
C19 C20 H20 . . 120.1
C15 C20 H20 . . 120.1
O1 C21 O2 . . 119.81(18)
O1 C21 C15 . . 121.14(17)
O2 C21 C15 . . 119.05(17)
O1 C21 Ni1 . . 61.83(10)
O2 C21 Ni1 . . 57.98(10)
C15 C21 Ni1 . . 176.47(14)
O4 C22 O3 . . 123.28(17)
O4 C22 C17 . . 121.69(17)
O3 C22 C17 . . 115.03(17)
O4 C22 Ni1 . 4_576 76.10(11)
O3 C22 Ni1 . 4_576 47.27(9)
C17 C22 Ni1 . 4_576 161.87(14)
O5 C23 O6 . . 124.48(19)
O5 C23 C19 . . 119.57(19)
O6 C23 C19 . . 115.95(17)
C3 N1 C1 . . 105.56(17)
C3 N1 Ni1 . . 124.38(14)
C1 N1 Ni1 . . 129.70(13)
C3 N2 C2 . . 107.20(17)
C3 N2 C4 . . 125.27(17)
C2 N2 C4 . . 127.28(17)
C14 N3 C13 . . 105.04(18)
C14 N3 Ni1 . 4_576 121.73(13)
C13 N3 Ni1 . 4_576 132.99(15)
C14 N4 C12 . . 106.24(19)
C14 N4 C11 . . 125.84(19)
C12 N4 C11 . . 127.90(19)
O3 Ni1 N1 4_575 . 102.93(7)
O3 Ni1 N3 4_575 4_575 91.32(7)
N1 Ni1 N3 . 4_575 98.09(7)
O3 Ni1 O2 4_575 . 159.66(6)
N1 Ni1 O2 . . 94.08(6)
N3 Ni1 O2 4_575 . 97.30(7)
O3 Ni1 O1 4_575 . 98.36(6)
N1 Ni1 O1 . . 151.61(6)
N3 Ni1 O1 4_575 . 99.98(7)
O2 Ni1 O1 . . 62.07(6)
O3 Ni1 C21 4_575 . 128.94(7)
N1 Ni1 C21 . . 123.80(6)
N3 Ni1 C21 4_575 . 100.42(7)
O2 Ni1 C21 . . 31.25(6)
O1 Ni1 C21 . . 30.82(5)
O3 Ni1 O4 4_575 4_575 55.55(6)
N1 Ni1 O4 . 4_575 90.24(6)
N3 Ni1 O4 4_575 4_575 146.87(6)
O2 Ni1 O4 . 4_575 114.10(6)
O1 Ni1 O4 . 4_575 86.47(6)
C21 Ni1 O4 . 4_575 101.30(6)
O3 Ni1 C22 4_575 4_575 28.18(6)
N1 Ni1 C22 . 4_575 98.21(6)
N3 Ni1 C22 4_575 4_575 119.48(7)
O2 Ni1 C22 . 4_575 138.73(7)
O1 Ni1 C22 . 4_575 91.73(6)
C21 Ni1 C22 . 4_575 116.78(6)
O4 Ni1 C22 4_575 4_575 27.41(5)
C21 O1 Ni1 . . 87.34(12)
C21 O2 Ni1 . . 90.77(12)
C22 O3 Ni1 . 4_576 104.55(12)
C22 O4 Ni1 . 4_576 76.49(11)
C23 O6 H61 . . 110(3)
H71 O7 H72 . . 107.7
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
C1 C2 . 1.355(3) ?
C1 N1 . 1.377(3) ?
C1 H1 . 0.9300 ?
C2 N2 . 1.369(3) ?
C2 H2 . 0.9300 ?
C3 N1 . 1.318(3) ?
C3 N2 . 1.340(3) ?
C3 H3 . 0.9300 ?
C4 N2 . 1.476(2) ?
C4 C5 . 1.508(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C10 . 1.387(3) ?
C5 C6 . 1.393(3) ?
C6 C7 . 1.377(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.385(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.383(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.393(3) ?
C9 C11 . 1.520(3) ?
C10 H10 . 0.9300 ?
C11 N4 . 1.455(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.342(3) ?
C12 N4 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 N3 . 1.382(3) ?
C13 H13 . 0.9300 ?
C14 N3 . 1.318(3) ?
C14 N4 . 1.346(3) ?
C14 H14 . 0.9300 ?
C15 C20 . 1.390(3) ?
C15 C16 . 1.392(3) ?
C15 C21 . 1.491(3) ?
C16 C17 . 1.381(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.392(3) ?
C17 C22 . 1.515(2) ?
C18 C19 . 1.395(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.388(3) ?
C19 C23 . 1.495(3) ?
C20 H20 . 0.9300 ?
C21 O1 . 1.258(2) ?
C21 O2 . 1.272(2) ?
C21 Ni1 . 2.452(2) ?
C22 O4 . 1.233(2) ?
C22 O3 . 1.271(2) ?
C22 Ni1 4_576 2.6057(18) ?
C23 O5 . 1.242(2) ?
C23 O6 . 1.275(3) ?
Ni1 N1 . 2.0157(17) y
N3 Ni1 4_576 2.0390(17) y
Ni1 O3 4_575 1.9775(15) y
Ni1 N3 4_575 2.0390(17) ?
Ni1 O2 . 2.0794(15) y
Ni1 O1 . 2.1642(15) y
Ni1 O4 4_575 2.6013(16) y
Ni1 C22 4_575 2.6057(19) ?
O3 Ni1 4_576 1.9775(15) ?
O4 Ni1 4_576 2.6013(16) ?
O6 H61 . 0.858(10) ?
O7 H71 . 0.8500 ?
O7 H72 . 0.8501 ?
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
O6 H61 O5 3_766 0.858(10) 1.789(12) 2.641(2) 171(4)
O7 H71 O5 . 0.85 2.44 3.251(6) 159.2
O7 H72 O2 1_655 0.85 2.05 2.887(4) 166.8
