#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/18/2221853.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_2221853
loop_
_publ_author_name
'Zhou, Dong'
'Shao, Min'
'He, Xiang'
'Zhao, Yongmei'
'Zhu, Shourong'
_publ_section_title
;μ-Biphenyl-3,3',4,4'-tetracarboxylato-κ²O³:O^3'^-bis[triaqua(2,2'-bipyridyl-κ²N,N')nickel(II)]
 hexahydrate
;
_journal_coeditor_code           WM2225
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m562
_journal_page_last               m563
_journal_paper_doi               10.1107/S1600536809014639
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'[Ni2 (C16 H6 O8) (C10 H8 N2)2 (H2 O)6], 6H2 O'
_chemical_formula_moiety         'C36 H34 N4 Ni2 O14, 6H2 O'
_chemical_formula_sum            'C36 H46 N4 Ni2 O20'
_chemical_formula_weight         972.19
_chemical_name_systematic
;
μ-Biphenyl-3,3',4,4'-tetracarboxylato-κ²O³:O^3'^-
bis[triaqua(2,2'-bipyridyl-κ²N,N')nickel(II)] hexahydrate
;
_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
_cell_angle_alpha                105.445(2)
_cell_angle_beta                 98.075(2)
_cell_angle_gamma                92.162(3)
_cell_formula_units_Z            1
_cell_length_a                   7.5126(14)
_cell_length_b                   12.088(2)
_cell_length_c                   12.285(2)
_cell_measurement_reflns_used    1042
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.16
_cell_measurement_theta_min      2.75
_cell_volume                     1061.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'DIAMOND (Brandenburg & Putz, 2006) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5556
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  0.8680
_exptl_absorpt_correction_T_min  0.8294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            light-blue
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flat
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.533
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/[σ²(Fo²)+(0.0835P)²+0.0076P]
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                2526
_reflns_number_total             3698
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wm2225.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_database_code               2221853
_cod_database_fobs_code          2221853
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
Ni Ni1 0.76324(9) 0.27456(6) 0.46907(5) 0.0292(2) Uani d . 1 . .
C C1 0.8729(8) 0.3451(5) 0.2678(4) 0.0353(13) Uani d . 1 . .
C C2 0.8455(7) 0.4289(4) 0.1965(4) 0.0279(12) Uani d . 1 . .
C C3 0.7072(7) 0.5022(4) 0.2062(4) 0.0271(11) Uani d . 1 . .
C C4 0.6778(8) 0.5682(5) 0.1309(5) 0.0390(14) Uani d . 1 . .
H H4 0.5816 0.6146 0.1345 0.047 Uiso calc R 1 . .
C C5 0.7894(8) 0.5668(5) 0.0497(5) 0.0439(16) Uani d . 1 . .
H H5 0.7662 0.6122 -0.0002 0.053 Uiso calc R 1 . .
C C6 0.9365(7) 0.4985(4) 0.0411(4) 0.0294(12) Uani d . 1 . .
C C7 0.9582(7) 0.4283(4) 0.1148(4) 0.0325(13) Uani d . 1 . .
H H7 1.0511 0.3793 0.1095 0.039 Uiso calc R 1 . .
C C8 0.5935(8) 0.5223(4) 0.3010(5) 0.0319(13) Uani d . 1 . .
C C9 0.7786(9) 0.2720(6) 0.7187(5) 0.0498(16) Uani d . 1 . .
H H9 0.7915 0.3519 0.7363 0.060 Uiso calc R 1 . .
C C10 0.7713(11) 0.2212(7) 0.8067(6) 0.071(2) Uani d . 1 . .
H H10 0.7805 0.2658 0.8820 0.086 Uiso calc R 1 . .
C C11 0.7506(12) 0.1055(7) 0.7801(7) 0.078(2) Uani d . 1 . .
H H11 0.7430 0.0692 0.8374 0.093 Uiso calc R 1 . .
C C12 0.7407(10) 0.0414(6) 0.6699(6) 0.064(2) Uani d . 1 . .
H H12 0.7271 -0.0385 0.6516 0.077 Uiso calc R 1 . .
C C13 0.7509(7) 0.0962(5) 0.5854(5) 0.0384(14) Uani d . 1 . .
C C14 0.7468(7) 0.0348(5) 0.4639(5) 0.0362(13) Uani d . 1 . .
C C15 0.7461(9) -0.0842(5) 0.4239(6) 0.0596(19) Uani d . 1 . .
H H15 0.7454 -0.1292 0.4745 0.072 Uiso calc R 1 . .
C C16 0.7463(11) -0.1351(6) 0.3104(7) 0.075(2) Uani d . 1 . .
H H16 0.7468 -0.2147 0.2837 0.091 Uiso calc R 1 . .
C C17 0.7460(10) -0.0692(6) 0.2371(6) 0.070(2) Uani d . 1 . .
H H17 0.7472 -0.1023 0.1597 0.084 Uiso calc R 1 . .
C C18 0.7437(8) 0.0492(5) 0.2803(5) 0.0490(16) Uani d . 1 . .
H H18 0.7395 0.0946 0.2297 0.059 Uiso calc R 1 . .
N N1 0.7680(6) 0.2112(4) 0.6097(4) 0.0375(11) Uani d . 1 . .
N N2 0.7472(6) 0.1002(4) 0.3901(4) 0.0333(10) Uani d . 1 . .
O O1 0.7508(5) 0.3349(3) 0.3258(3) 0.0327(9) Uani d . 1 . .
O O2 1.0074(6) 0.2870(4) 0.2630(4) 0.0519(12) Uani d . 1 . .
O O3 0.6703(5) 0.5796(3) 0.3995(3) 0.0357(9) Uani d . 1 . .
O O4 0.4305(5) 0.4876(3) 0.2757(3) 0.0414(10) Uani d . 1 . .
O O1W 0.7793(5) 0.4475(3) 0.5584(3) 0.0378(9) Uani d . 1 . .
H H1WA 0.7075 0.4576 0.6039 0.045 Uiso d R 1 . .
H H1WB 0.7528 0.4864 0.5108 0.045 Uiso d R 1 . .
O O2W 1.0407(5) 0.2754(3) 0.4820(3) 0.0366(9) Uani d . 1 . .
H H2WA 1.0698 0.2647 0.4183 0.044 Uiso d R 1 . .
H H2WB 1.0810 0.3312 0.5383 0.044 Uiso d R 1 . .
O O3W 0.4835(5) 0.2653(3) 0.4440(3) 0.0372(9) Uani d . 1 . .
H H3WA 0.4238 0.3141 0.4852 0.045 Uiso d R 1 . .
H H3WB 0.4455 0.2638 0.3776 0.045 Uiso d R 1 . .
O O4W 0.3480(6) 0.2550(4) 0.2175(4) 0.0662(13) Uani d . 1 . .
H H4WA 0.2365 0.2698 0.2201 0.079 Uiso d R 1 . .
H H4WB 0.3472 0.2363 0.1454 0.079 Uiso d R 1 . .
O O5W 0.3527(11) 0.0578(6) 0.0358(6) 0.141(3) Uani d . 1 . .
H H5WA 0.4255 0.1162 0.0371 0.169 Uiso d R 1 . .
H H5WB 0.3141 -0.0088 -0.0025 0.169 Uiso d R 1 . .
O O6W 0.9624(19) 0.0848(9) 0.0429(9) 0.288(7) Uani d . 1 . .
H H6WA 0.9844 0.1042 0.1156 0.345 Uiso d R 1 . .
H H6WB 0.9808 0.1578 0.0631 0.345 Uiso d 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
N2 Ni1 N1 . . 80.00(17) ?
N2 Ni1 O2W . . 88.41(16) ?
N1 Ni1 O2W . . 91.05(16) ?
N2 Ni1 O1 . . 98.95(15) ?
N1 Ni1 O1 . . 178.17(17) ?
O2W Ni1 O1 . . 90.43(14) ?
N2 Ni1 O3W . . 88.32(16) ?
N1 Ni1 O3W . . 91.12(16) ?
O2W Ni1 O3W . . 175.71(14) ?
O1 Ni1 O3W . . 87.34(14) ?
N2 Ni1 O1W . . 176.34(15) ?
N1 Ni1 O1W . . 96.33(16) ?
O2W Ni1 O1W . . 91.76(15) ?
O1 Ni1 O1W . . 84.71(14) ?
O3W Ni1 O1W . . 91.67(14) ?
O2 C1 O1 . . 123.8(5) ?
O2 C1 C2 . . 119.8(4) ?
O1 C1 C2 . . 116.3(5) ?
C3 C2 C7 . . 119.6(4) ?
C3 C2 C1 . . 121.8(4) ?
C7 C2 C1 . . 118.6(4) ?
C4 C3 C2 . . 119.0(4) ?
C4 C3 C8 . . 116.6(4) ?
C2 C3 C8 . . 124.2(4) ?
C3 C4 C5 . . 121.1(5) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C4 C5 C6 . . 121.6(5) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C7 C6 C5 . . 116.1(4) ?
C7 C6 C6 . 2_765 121.8(6) ?
C5 C6 C6 . 2_765 122.1(6) ?
C6 C7 C2 . . 122.5(5) ?
C6 C7 H7 . . 118.8 ?
C2 C7 H7 . . 118.8 ?
O4 C8 O3 . . 125.0(5) ?
O4 C8 C3 . . 118.2(5) ?
O3 C8 C3 . . 116.7(5) ?
N1 C9 C10 . . 122.8(6) ?
N1 C9 H9 . . 118.6 ?
C10 C9 H9 . . 118.6 ?
C11 C10 C9 . . 118.1(7) ?
C11 C10 H10 . . 120.9 ?
C9 C10 H10 . . 120.9 ?
C10 C11 C12 . . 120.3(6) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C11 C12 C13 . . 119.4(7) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
N1 C13 C12 . . 121.3(6) ?
N1 C13 C14 . . 115.0(5) ?
C12 C13 C14 . . 123.7(6) ?
N2 C14 C15 . . 119.8(6) ?
N2 C14 C13 . . 116.8(5) ?
C15 C14 C13 . . 123.4(5) ?
C16 C15 C14 . . 120.2(6) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C17 C16 C15 . . 119.6(7) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C16 C17 C18 . . 118.4(7) ?
C16 C17 H17 . . 120.8 ?
C18 C17 H17 . . 120.8 ?
N2 C18 C17 . . 122.8(6) ?
N2 C18 H18 . . 118.6 ?
C17 C18 H18 . . 118.6 ?
C9 N1 C13 . . 118.1(5) ?
C9 N1 Ni1 . . 127.2(4) ?
C13 N1 Ni1 . . 114.7(4) ?
C18 N2 C14 . . 119.1(5) ?
C18 N2 Ni1 . . 127.5(4) ?
C14 N2 Ni1 . . 113.3(4) ?
C1 O1 Ni1 . . 129.2(3) ?
Ni1 O1W H1WA . . 109.6 ?
Ni1 O1W H1WB . . 108.5 ?
H1WA O1W H1WB . . 109.4 ?
Ni1 O2W H2WA . . 109.7 ?
Ni1 O2W H2WB . . 105.3 ?
H2WA O2W H2WB . . 124.6 ?
Ni1 O3W H3WA . . 122.7 ?
Ni1 O3W H3WB . . 109.6 ?
H3WA O3W H3WB . . 105.8 ?
H4WA O4W H4WB . . 100.3 ?
H5WA O5W H5WB . . 143.0 ?
H6WA O6W H6WB . . 74.3 ?
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
Ni1 N2 . 2.063(4) y
Ni1 N1 . 2.064(4) y
Ni1 O2W . 2.067(3) y
Ni1 O1 . 2.069(3) y
Ni1 O3W . 2.075(3) y
Ni1 O1W . 2.076(4) y
C1 O2 . 1.252(6) ?
C1 O1 . 1.259(6) ?
C1 C2 . 1.508(7) ?
C2 C3 . 1.388(7) ?
C2 C7 . 1.400(6) ?
C3 C4 . 1.375(7) ?
C3 C8 . 1.513(7) ?
C4 C5 . 1.387(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.403(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.394(7) ?
C6 C6 2_765 1.489(9) ?
C7 H7 . 0.9300 ?
C8 O4 . 1.248(6) ?
C8 O3 . 1.266(6) ?
C9 N1 . 1.334(7) ?
C9 C10 . 1.384(8) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.347(9) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.359(10) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.380(8) ?
C12 H12 . 0.9300 ?
C13 N1 . 1.340(7) ?
C13 C14 . 1.475(8) ?
C14 N2 . 1.352(7) ?
C14 C15 . 1.390(8) ?
C15 C16 . 1.366(9) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.351(10) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.390(8) ?
C17 H17 . 0.9300 ?
C18 N2 . 1.322(7) ?
C18 H18 . 0.9300 ?
O1W H1WA . 0.8201 ?
O1W H1WB . 0.8498 ?
O2W H2WA . 0.8201 ?
O2W H2WB . 0.8379 ?
O3W H3WA . 0.8542 ?
O3W H3WB . 0.8200 ?
O4W H4WA . 0.8664 ?
O4W H4WB . 0.8528 ?
O5W H5WA . 0.8722 ?
O5W H5WB . 0.8339 ?
O6W H6WA . 0.8500 ?
O6W H6WB . 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 H1WA O4 2_666 0.82 1.91 2.720(5) 167.6
O1W H1WB O3 . 0.85 2.04 2.889(5) 175.8
O2W H2WA O2 . 0.82 1.99 2.708(5) 145.6
O2W H2WB O3 2_766 0.84 2.06 2.715(5) 134.6
O3W H3WA O3 2_666 0.85 1.88 2.723(5) 168.2
O3W H3WB O4W . 0.82 1.97 2.793(6) 177.9
O4W H4WA O2 1_455 0.87 1.87 2.715(6) 163.7
O4W H4WB O5W . 0.85 2.22 2.803(8) 125.2
O5W H5WB O6W 2_655 0.83 2.18 2.770(15) 128.3
O6W H6WA O2 . 0.85 2.44 3.091(11) 134.2
O6W H6WA O2 . 0.85 2.44 3.091(11) 134.2
