#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/31/2223104.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_2223104
loop_
_publ_author_name
'Lian, Heng-Chi'
'Ni, Qing-Ling'
'Jiang, Xuan-Feng'
'Cen, Zhong-Min'
'Lin, Jia-Huang'
_publ_section_title
;
 Tetraaquabis(2-methylbenzimidazolium-1,3-diacetato-κO)zinc(II)
 tetrahydrate
;
_journal_coeditor_code           HK2732
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1091
_journal_paper_doi               10.1107/S1600536809031766
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Zn (C12 H11 N2 O4)2 (H2 O)4], 4H2 O'
_chemical_formula_moiety         'C24 H30 N4 O12 Zn, 4(H2 O)'
_chemical_formula_sum            'C24 H38 N4 O16 Zn'
_chemical_formula_weight         703.95
_chemical_name_systematic
;
Tetraaquabis(2-methylbenzimidazolium-1,3-diacetato-κO)zinc(II)
tetrahydrate
;
_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                 104.467(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2749(9)
_cell_length_b                   21.265(3)
_cell_length_c                   9.7794(12)
_cell_measurement_reflns_used    3729
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.35
_cell_volume                     1464.9(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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      294(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7436
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.8740
_exptl_absorpt_correction_T_min  0.7567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.981
_refine_diff_density_min         -0.506
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0355
_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)+(0.0541P)²+0.4211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                2582
_reflns_number_total             3202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2732.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223104
_cod_database_fobs_code          2223104
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
Zn Zn1 0.0000 0.0000 0.0000 0.01544(12) Uani d S 1 . .
O O1 0.1738(2) 0.37790(7) -0.04309(16) 0.0235(4) Uani d . 1 . .
O O2 0.3049(2) 0.44774(7) 0.12371(16) 0.0225(4) Uani d . 1 . .
O O3 0.1638(2) 0.13757(7) -0.05157(16) 0.0203(3) Uani d . 1 . .
O O4 0.2586(2) 0.05044(7) 0.07499(16) 0.0190(3) Uani d . 1 . .
O O5 -0.0725(3) 0.01888(8) 0.19098(18) 0.0210(4) Uani d . 1 . .
H H5A -0.012(5) -0.0003(15) 0.242(4) 0.042(11) Uiso d . 1 . .
H H5B -0.180(5) 0.0100(13) 0.190(3) 0.030(8) Uiso d . 1 . .
O O6 -0.1608(2) 0.07925(7) -0.08958(19) 0.0201(3) Uani d . 1 . .
H H6A -0.054(5) 0.1041(17) -0.080(4) 0.065(11) Uiso d . 1 . .
H H6B -0.191(4) 0.0718(15) -0.167(3) 0.038(9) Uiso d . 1 . .
O O7 -0.8479(3) 0.55949(9) -0.00644(19) 0.0270(4) Uani d . 1 . .
H H7A -0.940(6) 0.5704(19) 0.012(3) 0.060(12) Uiso d . 1 . .
H H7B -0.814(5) 0.5299(17) 0.040(3) 0.041(9) Uiso d . 1 . .
O O8 -0.4182(3) -0.02154(9) 0.2126(2) 0.0255(4) Uani d . 1 . .
H H8A -0.505(5) -0.0026(12) 0.179(3) 0.021(7) Uiso d . 1 . .
H H8B -0.409(4) -0.0284(15) 0.294(3) 0.036(9) Uiso d . 1 . .
N N1 0.4887(2) 0.29835(8) 0.03733(19) 0.0149(4) Uani d . 1 . .
N N2 0.4950(2) 0.19548(8) 0.03276(18) 0.0145(4) Uani d . 1 . .
C C1 0.4865(3) 0.28122(10) -0.1007(2) 0.0157(4) Uani d . 1 . .
C C2 0.4759(3) 0.31727(10) -0.2218(2) 0.0197(5) Uani d . 1 . .
H H2A 0.4753 0.3610 -0.2199 0.024 Uiso calc R 1 . .
C C3 0.4664(3) 0.28382(11) -0.3447(2) 0.0230(5) Uani d . 1 . .
H H3A 0.4599 0.3059 -0.4279 0.028 Uiso calc R 1 . .
C C4 0.4661(3) 0.21788(11) -0.3484(2) 0.0225(5) Uani d . 1 . .
H H4A 0.4567 0.1976 -0.4341 0.027 Uiso calc R 1 . .
C C5 0.4795(3) 0.18208(10) -0.2272(2) 0.0194(5) Uani d . 1 . .
H H5C 0.4811 0.1384 -0.2286 0.023 Uiso calc R 1 . .
C C6 0.4903(3) 0.21592(10) -0.1039(2) 0.0152(4) Uani d . 1 . .
C C7 0.4906(3) 0.24587(9) 0.1143(2) 0.0147(4) Uani d . 1 . .
C C8 0.4841(3) 0.24357(10) 0.2639(2) 0.0198(5) Uani d . 1 . .
H H8C 0.4816 0.2856 0.2992 0.030 Uiso calc R 1 . .
H H8D 0.5944 0.2221 0.3181 0.030 Uiso calc R 1 . .
H H8E 0.3720 0.2215 0.2718 0.030 Uiso calc R 1 . .
C C9 0.4878(3) 0.12953(9) 0.0736(2) 0.0158(4) Uani d . 1 . .
H H9A 0.5342 0.1257 0.1752 0.019 Uiso calc R 1 . .
H H9B 0.5697 0.1048 0.0301 0.019 Uiso calc R 1 . .
C C10 0.2853(3) 0.10399(9) 0.0281(2) 0.0148(4) Uani d . 1 . .
C C11 0.4965(3) 0.36335(9) 0.0885(2) 0.0177(4) Uani d . 1 . .
H H11A 0.5867 0.3866 0.0498 0.021 Uiso calc R 1 . .
H H11B 0.5441 0.3631 0.1905 0.021 Uiso calc R 1 . .
C C12 0.3065(3) 0.39821(9) 0.0510(2) 0.0161(4) Uani d . 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'
Zn Zn 0.2839 1.4301 '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
O5 Zn1 O5 . 3 180.00(14) ?
O5 Zn1 O6 . 3 91.13(7) yes
O5 Zn1 O6 3 3 88.87(7) ?
O5 Zn1 O6 . . 88.87(7) yes
O5 Zn1 O6 3 . 91.13(7) ?
O6 Zn1 O6 3 . 180.00(9) ?
O5 Zn1 O4 . . 89.65(7) yes
O5 Zn1 O4 3 . 90.35(7) yes
O6 Zn1 O4 3 . 84.78(6) yes
O6 Zn1 O4 . . 95.22(6) yes
O5 Zn1 O4 . 3 90.35(7) yes
O5 Zn1 O4 3 3 89.65(7) yes
O6 Zn1 O4 3 3 95.22(6) ?
O6 Zn1 O4 . 3 84.78(6) ?
O4 Zn1 O4 . 3 180.00(12) ?
C10 O4 Zn1 . . 122.18(13) ?
Zn1 O5 H5A . . 106(3) ?
Zn1 O5 H5B . . 114(2) ?
H5A O5 H5B . . 108(4) ?
Zn1 O6 H6A . . 93(2) ?
Zn1 O6 H6B . . 104(2) ?
H6A O6 H6B . . 104(3) ?
H7A O7 H7B . . 106(4) ?
H8A O8 H8B . . 113(3) ?
C7 N1 C1 . . 108.75(17) ?
C7 N1 C11 . . 126.66(18) ?
C1 N1 C11 . . 124.53(17) ?
C7 N2 C6 . . 108.77(17) ?
C7 N2 C9 . . 126.57(17) ?
C6 N2 C9 . . 124.43(17) ?
C6 C1 N1 . . 106.69(18) ?
C6 C1 C2 . . 121.8(2) ?
N1 C1 C2 . . 131.5(2) ?
C3 C2 C1 . . 115.8(2) ?
C3 C2 H2A . . 122.1 ?
C1 C2 H2A . . 122.1 ?
C2 C3 C4 . . 122.4(2) ?
C2 C3 H3A . . 118.8 ?
C4 C3 H3A . . 118.8 ?
C5 C4 C3 . . 121.7(2) ?
C5 C4 H4A . . 119.2 ?
C3 C4 H4A . . 119.2 ?
C6 C5 C4 . . 115.6(2) ?
C6 C5 H5C . . 122.2 ?
C4 C5 H5C . . 122.2 ?
C5 C6 C1 . . 122.7(2) ?
C5 C6 N2 . . 130.64(19) ?
C1 C6 N2 . . 106.58(18) ?
N2 C7 N1 . . 109.18(18) ?
N2 C7 C8 . . 125.07(19) ?
N1 C7 C8 . . 125.74(19) ?
C7 C8 H8C . . 109.5 ?
C7 C8 H8D . . 109.5 ?
H8C C8 H8D . . 109.5 ?
C7 C8 H8E . . 109.5 ?
H8C C8 H8E . . 109.5 ?
H8D C8 H8E . . 109.5 ?
N2 C9 C10 . . 111.03(16) ?
N2 C9 H9A . . 109.4 ?
C10 C9 H9A . . 109.4 ?
N2 C9 H9B . . 109.4 ?
C10 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
O3 C10 O4 . . 126.52(19) ?
O3 C10 C9 . . 117.38(18) ?
O4 C10 C9 . . 116.09(17) ?
N1 C11 C12 . . 114.77(17) ?
N1 C11 H11A . . 108.6 ?
C12 C11 H11A . . 108.6 ?
N1 C11 H11B . . 108.6 ?
C12 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
O1 C12 O2 . . 126.3(2) ?
O1 C12 C11 . . 120.08(18) ?
O2 C12 C11 . . 113.60(18) ?
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
Zn1 O5 . 2.1023(17) yes
Zn1 O5 3 2.1023(17) ?
Zn1 O6 3 2.1128(16) ?
Zn1 O6 . 2.1128(16) yes
Zn1 O4 . 2.1303(14) yes
Zn1 O4 3 2.1303(14) ?
O1 C12 . 1.233(3) ?
O2 C12 . 1.273(2) ?
O3 C10 . 1.247(2) ?
O4 C10 . 1.261(2) ?
O5 H5A . 0.71(3) ?
O5 H5B . 0.80(4) ?
O6 H6A . 0.92(4) ?
O6 H6B . 0.75(3) ?
O7 H7A . 0.78(4) ?
O7 H7B . 0.78(4) ?
O8 H8A . 0.75(3) ?
O8 H8B . 0.79(3) ?
N1 C7 . 1.345(3) ?
N1 C1 . 1.394(3) ?
N1 C11 . 1.466(3) ?
N2 C7 . 1.341(3) ?
N2 C6 . 1.398(3) ?
N2 C9 . 1.463(2) ?
C1 C6 . 1.390(3) ?
C1 C2 . 1.396(3) ?
C2 C3 . 1.384(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.402(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.392(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.389(3) ?
C5 H5C . 0.9300 ?
C7 C8 . 1.476(3) ?
C8 H8C . 0.9600 ?
C8 H8D . 0.9600 ?
C8 H8E . 0.9600 ?
C9 C10 . 1.528(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 C12 . 1.531(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
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
O5 H5B O8 . 0.80(4) 1.92(4) 2.716(3) 170(3)
O6 H6A O3 . 0.92(4) 1.70(4) 2.610(2) 170(3)
O6 H6B O2 4_565 0.75(3) 2.08(3) 2.811(2) 164(3)
O7 H7A O1 3_465 0.78(4) 2.11(4) 2.864(3) 165(4)
O7 H7B O2 1_455 0.78(4) 2.03(4) 2.792(2) 167(3)
O8 H8A O4 1_455 0.75(3) 2.10(3) 2.846(2) 177(3)
O8 H8B O7 4_666 0.79(3) 2.00(3) 2.786(3) 168(3)
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
O5 Zn1 O4 C10 . . . . -107.15(16) ?
O5 Zn1 O4 C10 3 . . . 72.85(16) ?
O6 Zn1 O4 C10 3 . . . 161.69(16) ?
O6 Zn1 O4 C10 . . . . -18.31(16) ?
C7 N1 C1 C6 . . . . -1.0(2) ?
C11 N1 C1 C6 . . . . 176.50(17) ?
C7 N1 C1 C2 . . . . 176.8(2) ?
C11 N1 C1 C2 . . . . -5.7(3) ?
C6 C1 C2 C3 . . . . 1.0(3) ?
N1 C1 C2 C3 . . . . -176.5(2) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . -1.4(3) ?
C3 C4 C5 C6 . . . . 0.9(3) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C4 C5 C6 N2 . . . . 176.3(2) ?
N1 C1 C6 C5 . . . . 176.56(18) ?
C2 C1 C6 C5 . . . . -1.5(3) ?
N1 C1 C6 N2 . . . . -0.1(2) ?
C2 C1 C6 N2 . . . . -178.15(18) ?
C7 N2 C6 C5 . . . . -175.2(2) ?
C9 N2 C6 C5 . . . . -0.4(3) ?
C7 N2 C6 C1 . . . . 1.1(2) ?
C9 N2 C6 C1 . . . . 175.92(17) ?
C6 N2 C7 N1 . . . . -1.8(2) ?
C9 N2 C7 N1 . . . . -176.41(17) ?
C6 N2 C7 C8 . . . . 176.87(19) ?
C9 N2 C7 C8 . . . . 2.2(3) ?
C1 N1 C7 N2 . . . . 1.7(2) ?
C11 N1 C7 N2 . . . . -175.70(17) ?
C1 N1 C7 C8 . . . . -176.92(19) ?
C11 N1 C7 C8 . . . . 5.7(3) ?
C7 N2 C9 C10 . . . . 96.0(2) ?
C6 N2 C9 C10 . . . . -77.8(2) ?
Zn1 O4 C10 O3 . . . . 9.4(3) ?
Zn1 O4 C10 C9 . . . . -170.20(13) ?
N2 C9 C10 O3 . . . . 9.8(3) ?
N2 C9 C10 O4 . . . . -170.54(17) ?
C7 N1 C11 C12 . . . . -103.4(2) ?
C1 N1 C11 C12 . . . . 79.6(2) ?
N1 C11 C12 O1 . . . . -17.0(3) ?
N1 C11 C12 O2 . . . . 163.61(18) ?
