#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/35/2223501.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_2223501
loop_
_publ_author_name
'Wang, Hao'
'Song, Wen-Dong'
'Li, Shi-Jie'
'Qin, Pei-Wen'
'Hu, Shi-Wei'
_publ_section_title
;Tetraaquabis(6-carboxy-1H-benzimidazole-5-carboxylato-κN³)nickel(II)
 dimethylformamide disolvate dihydrate
;
_journal_coeditor_code           NG2646
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1258
_journal_paper_doi               10.1107/S1600536809038069
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'[Ni (C9 H5 N2 O4)2 (H2 O)4], 2C3 H7 N O, 2H2 O'
_chemical_formula_moiety         'C18 H18 N4 Ni O12, 2(C3 H7 N O), 2(H2 O)'
_chemical_formula_sum            'C24 H36 N6 Ni O16'
_chemical_formula_weight         723.30
_chemical_name_systematic
;
Tetraaquabis(6-carboxy-1H-benzimidazole-5-carboxylato-
κN³)nickel(II) dimethylformamide disolvate dihydrate
;
_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                100.80(3)
_cell_angle_beta                 103.03(3)
_cell_angle_gamma                114.04(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5327(17)
_cell_length_b                   9.1387(18)
_cell_length_c                   11.624(2)
_cell_measurement_reflns_used    3600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1.36
_cell_volume                     765.7(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL9 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6116
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         3.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.8875
_exptl_absorpt_correction_T_min  0.8295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0371
_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+0.01P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                2613
_reflns_number_total             2737
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2646.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        765.7(3)
_cod_database_code               2223501
_cod_database_fobs_code          2223501
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
C C1 0.2895(3) 0.4030(3) 0.2261(2) 0.0301(5) Uani d . 1 . .
H H1 0.2030 0.3062 0.2339 0.036 Uiso calc R 1 . .
N N1 0.4387(2) 0.5153(2) 0.31852(17) 0.0272(4) Uani d . 1 . .
Ni Ni1 0.5000 0.5000 0.5000 0.02200(19) Uani d S 1 . .
C C2 0.4271(3) 0.5938(3) 0.1432(2) 0.0272(5) Uani d . 1 . .
N N2 0.2739(2) 0.4415(2) 0.11945(17) 0.0324(4) Uani d . 1 . .
H H2 0.1861 0.3832 0.0499 0.039 Uiso calc R 1 . .
C C3 0.5296(3) 0.6391(3) 0.2686(2) 0.0252(4) Uani d . 1 . .
O O3W 0.75996(16) 0.54366(16) 0.50333(12) 0.0345(4) Uani d D 1 . .
C C4 0.6923(3) 0.7892(3) 0.3224(2) 0.0271(5) Uani d . 1 . .
H H4 0.7612 0.8210 0.4056 0.033 Uiso calc R 1 . .
C C5 0.7498(3) 0.8909(3) 0.2494(2) 0.0248(4) Uani d . 1 . .
O O1 0.9319(2) 1.1775(2) 0.37262(18) 0.0456(5) Uani d . 1 . .
C C6 0.6429(3) 0.8423(3) 0.1223(2) 0.0280(5) Uani d . 1 . .
O O2 1.0690(2) 1.0376(2) 0.3063(2) 0.0522(5) Uani d . 1 . .
C C7 0.4811(3) 0.6925(3) 0.0690(2) 0.0307(5) Uani d . 1 . .
H H7 0.4113 0.6596 -0.0141 0.037 Uiso calc R 1 . .
C C8 0.6944(3) 0.9451(3) 0.0384(2) 0.0327(5) Uani d . 1 . .
C C9 0.9321(3) 1.0500(3) 0.31293(19) 0.0261(5) Uani d . 1 . .
O O2W 0.41483(16) 0.24688(15) 0.42925(12) 0.0295(4) Uani d D 1 . .
H H6W 0.8553 0.6369 0.5347 0.044 Uiso d RD 1 . .
H H5W 0.7568 0.4874 0.4361 0.044 Uiso d RD 1 . .
H H3W 0.4755 0.2330 0.3845 0.044 Uiso d RD 1 . .
H H4W 0.3028 0.1830 0.3922 0.044 Uiso d RD 1 . .
O O3 0.6082(3) 0.8962(3) -0.07127(17) 0.0591(6) Uani d . 1 . .
O O4 0.8343(3) 1.0927(3) 0.09199(18) 0.0633(7) Uani d . 1 . .
H H4A 0.8481 1.1446 0.0415 0.095 Uiso calc R 1 . .
O O1W 0.3424(2) 0.7464(3) 0.69171(17) 0.0487(5) Uani d D 1 . .
H H1W 0.3996 0.7866 0.7687 0.073 Uiso d RD 1 . .
H H2W 0.2637 0.7784 0.6716 0.073 Uiso d RD 1 . .
O O5 0.0718(2) 0.7407(2) 0.05904(16) 0.0462(5) Uani d . 1 . .
C C12 -0.0319(4) 0.5721(4) 0.2255(3) 0.0570(8) Uani d . 1 . .
H H12A -0.1264 0.6015 0.2316 0.086 Uiso calc R 1 . .
H H12B -0.0161 0.5128 0.2835 0.086 Uiso calc R 1 . .
H H12C -0.0653 0.5013 0.1426 0.086 Uiso calc R 1 . .
N N3 0.1376(3) 0.7248(3) 0.25427(18) 0.0352(5) Uani d . 1 . .
C C11 0.2581(4) 0.8066(4) 0.3847(2) 0.0522(7) Uani d . 1 . .
H H11A 0.3625 0.9074 0.3914 0.078 Uiso calc R 1 . .
H H11B 0.2971 0.7308 0.4129 0.078 Uiso calc R 1 . .
H H11C 0.1933 0.8351 0.4351 0.078 Uiso calc R 1 . .
C C10 0.1722(3) 0.7970(3) 0.1704(2) 0.0356(5) Uani d . 1 . .
H H10 0.2794 0.8978 0.1949 0.043 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'
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
_geom_angle_publ_flag
N1 C1 N2 . . 113.71(18) ?
N1 C1 H1 . . 123.1 ?
N2 C1 H1 . . 123.1 ?
C1 N1 C3 . . 104.99(18) ?
C1 N1 Ni1 . . 123.63(15) ?
C3 N1 Ni1 . . 131.30(15) ?
O2W Ni1 O2W . 2_666 180.0 ?
O2W Ni1 O3W . 2_666 91.85(6) ?
O2W Ni1 O3W 2_666 2_666 88.15(6) ?
O2W Ni1 O3W . . 88.15(6) ?
O2W Ni1 O3W 2_666 . 91.85(6) ?
O3W Ni1 O3W 2_666 . 180.0 ?
O2W Ni1 N1 . 2_666 90.06(7) ?
O2W Ni1 N1 2_666 2_666 89.94(7) ?
O3W Ni1 N1 2_666 2_666 90.14(7) ?
O3W Ni1 N1 . 2_666 89.86(7) ?
O2W Ni1 N1 . . 89.94(7) ?
O2W Ni1 N1 2_666 . 90.06(7) ?
O3W Ni1 N1 2_666 . 89.86(7) ?
O3W Ni1 N1 . . 90.14(7) ?
N1 Ni1 N1 2_666 . 180.0 ?
C7 C2 N2 . . 131.9(2) ?
C7 C2 C3 . . 122.56(19) ?
N2 C2 C3 . . 105.48(19) ?
C1 N2 C2 . . 106.79(18) ?
C1 N2 H2 . . 126.6 ?
C2 N2 H2 . . 126.6 ?
C4 C3 N1 . . 131.2(2) ?
C4 C3 C2 . . 119.76(19) ?
N1 C3 C2 . . 109.02(19) ?
Ni1 O3W H6W . . 126.3 ?
Ni1 O3W H5W . . 111.1 ?
H6W O3W H5W . . 111.6 ?
C5 C4 C3 . . 118.77(19) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 120.39(19) ?
C4 C5 C9 . . 115.96(18) ?
C6 C5 C9 . . 123.63(19) ?
C7 C6 C5 . . 120.7(2) ?
C7 C6 C8 . . 115.74(19) ?
C5 C6 C8 . . 123.59(19) ?
C2 C7 C6 . . 117.85(19) ?
C2 C7 H7 . . 121.1 ?
C6 C7 H7 . . 121.1 ?
O3 C8 O4 . . 122.2(2) ?
O3 C8 C6 . . 122.5(2) ?
O4 C8 C6 . . 115.3(2) ?
O2 C9 O1 . . 125.6(2) ?
O2 C9 C5 . . 116.7(2) ?
O1 C9 C5 . . 117.58(18) ?
Ni1 O2W H3W . . 109.0 ?
Ni1 O2W H4W . . 117.7 ?
H3W O2W H4W . . 110.9 ?
C8 O4 H4A . . 109.5 ?
H1W O1W H2W . . 111.4 ?
N3 C12 H12A . . 109.5 ?
N3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C10 N3 C12 . . 121.1(2) ?
C10 N3 C11 . . 120.7(2) ?
C12 N3 C11 . . 117.8(2) ?
N3 C11 H11A . . 109.5 ?
N3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N3 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O5 C10 N3 . . 124.8(2) ?
O5 C10 H10 . . 117.6 ?
N3 C10 H10 . . 117.6 ?
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 N1 . 1.317(3) ?
C1 N2 . 1.344(3) ?
C1 H1 . 0.9300 ?
N1 C3 . 1.397(3) ?
N1 Ni1 . 2.1014(18) ?
Ni1 O2W . 2.0501(14) ?
Ni1 O2W 2_666 2.0501(14) ?
Ni1 O3W 2_666 2.0773(13) ?
Ni1 O3W . 2.0773(13) ?
Ni1 N1 2_666 2.1014(18) ?
C2 C7 . 1.379(3) ?
C2 N2 . 1.390(3) ?
C2 C3 . 1.401(3) ?
N2 H2 . 0.8600 ?
C3 C4 . 1.391(3) ?
O3W H6W . 0.8402 ?
O3W H5W . 0.8394 ?
C4 C5 . 1.391(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.424(3) ?
C5 C9 . 1.522(3) ?
O1 C9 . 1.240(3) ?
C6 C7 . 1.386(3) ?
C6 C8 . 1.492(3) ?
O2 C9 . 1.236(3) ?
C7 H7 . 0.9300 ?
C8 O3 . 1.209(3) ?
C8 O4 . 1.293(3) ?
O2W H3W . 0.8401 ?
O2W H4W . 0.8400 ?
O4 H4A . 0.8200 ?
O1W H1W . 0.8408 ?
O1W H2W . 0.8405 ?
O5 C10 . 1.252(3) ?
C12 N3 . 1.454(4) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
N3 C10 . 1.298(3) ?
N3 C11 . 1.470(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C10 H10 . 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
O1W H2W O1 2_676 0.84 1.86 2.693(3) 172.6
O1W H1W O3 1_556 0.84 2.00 2.801(3) 159.7
O4 H4A O5 2_675 0.82 1.78 2.585(3) 166.8
O2W H4W O2 1_445 0.84 1.79 2.624(3) 175.8
O2W H3W O1W 2_666 0.84 1.92 2.741(2) 166.3
O3W H5W O1W 2_666 0.84 2.06 2.810(3) 147.9
O3W H6W O1 2_776 0.84 1.81 2.634(3) 168.9
N2 H2 O5 2_565 0.86 1.98 2.779(3) 155.0
