#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:48:09 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179078 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/40/4304091.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4304091
loop_
_publ_author_name
'Meenakshi Ghosh'
'Papu Biswas'
'Ulrich Flörke'
'Kamalaksha Nag'
_publ_section_title
;
Halogen Exchange and Scrambling between C-X and M-X' Bonds in Copper,
Nickel, and Cobalt Complexes of 6,6'-bis(bromo/
chloromethyl)-2,2'-bipyridine. Structural, Electrochemical, and
Photochemical Studies
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              281
_journal_page_last               296
_journal_paper_doi               10.1021/ic7014786
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C12 H10 Br1.73 Cl2.27 N2 Ni, H2 O'
_chemical_formula_sum            'C12 H12 Br1.73 Cl2.27 N2 Ni O'
_chemical_formula_weight         477.66
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8515(6)
_cell_length_b                   7.6429(5)
_cell_length_c                   20.6049(13)
_cell_measurement_reflns_used    3998
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.36
_cell_volume                     1548.00(17)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  'SHELXTL (Bruker, 2002)'
_computing_structure_refinement  'SHELXTL (Bruker, 2002)'
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12236
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         3877
_exptl_absorpt_coefficient_mu    6.105
_exptl_absorpt_correction_T_max  0.3154
_exptl_absorpt_correction_T_min  0.1871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0321
_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)+(0.0501P)²+1.4543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                3129
_reflns_number_total             3666
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic7014786-file003_8.cif
_cod_data_source_block           12
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4304091
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.70416(6) 0.07814(8) 0.12761(2) 0.0206(3) Uani 0.833(2) 1 d P A 1
Br2 Br 0.9591(10) -0.4445(15) 0.1968(5) 0.0187(6) Uani 0.439(3) 1 d P A 1
Cl1 Cl 0.6997(15) 0.084(2) 0.1283(7) 0.041(2) Uiso 0.167(2) 1 d P A 2
Cl2 Cl 0.952(2) -0.432(3) 0.1912(11) 0.025(3) Uani 0.561(3) 1 d P A 2
Br3 Br 0.5344(13) -0.2487(12) -0.0077(4) 0.0387(19) Uani 0.232(4) 1 d P B 3
Br4 Br 1.0630(4) 0.0032(5) 0.3388(2) 0.0211(7) Uani 0.226(6) 1 d P A 3
Cl3 Cl 0.5482(9) -0.2521(9) -0.0097(3) 0.0350(11) Uani 0.768(4) 1 d P B 4
Cl4 Cl 1.0732(5) 0.0026(7) 0.3351(2) 0.071(3) Uani 0.774(6) 1 d P A 4
Ni1 Ni 0.86148(4) -0.15734(5) 0.162245(16) 0.01810(13) Uani 1 1 d . . .
N1 N 0.9018(3) -0.2203(3) 0.06990(11) 0.0233(5) Uani 1 1 d . A .
N2 N 1.0459(3) -0.0388(3) 0.16039(13) 0.0226(5) Uani 1 1 d . A .
O1 O 0.7850(2) -0.1493(3) 0.24965(11) 0.0311(5) Uani 1 1 d D A .
H1 H 0.721(3) -0.084(5) 0.259(2) 0.043(8) Uiso 1 1 d D . .
H2 H 0.803(4) -0.229(4) 0.2771(15) 0.043(8) Uiso 1 1 d D . .
C1 C 0.6806(4) -0.3516(5) 0.04589(18) 0.0383(9) Uani 1 1 d . . .
H1A H 0.6726 -0.3145 0.0915 0.046 Uiso 1 1 calc R B 3
H1B H 0.6714 -0.4805 0.0442 0.046 Uiso 1 1 calc R B 3
C2 C 0.8191(4) -0.3022(4) 0.02563(15) 0.0299(7) Uani 1 1 d . A .
C3 C 0.8648(5) -0.3441(5) -0.03584(16) 0.0400(9) Uani 1 1 d . . .
H3A H 0.8061 -0.4013 -0.0676 0.048 Uiso 1 1 calc R B .
C4 C 0.9964(5) -0.3007(5) -0.04932(16) 0.0431(10) Uani 1 1 d . B .
H4A H 1.0281 -0.3273 -0.0907 0.052 Uiso 1 1 calc R . .
C5 C 1.0806(4) -0.2203(5) -0.00371(16) 0.0370(9) Uani 1 1 d . . .
H5A H 1.1713 -0.1918 -0.0127 0.044 Uiso 1 1 calc R B .
C6 C 1.0314(3) -0.1803(4) 0.05665(15) 0.0258(7) Uani 1 1 d . A .
C7 C 1.1135(3) -0.0904(4) 0.10858(16) 0.0275(7) Uani 1 1 d . . .
C8 C 1.2518(4) -0.0526(5) 0.1054(2) 0.0371(8) Uani 1 1 d . A .
H8A H 1.2998 -0.0926 0.0698 0.045 Uiso 1 1 calc R . .
C9 C 1.3179(4) 0.0439(5) 0.1548(2) 0.0440(10) Uani 1 1 d . . .
H9A H 1.4122 0.0687 0.1539 0.053 Uiso 1 1 calc R A .
C10 C 1.2463(4) 0.1033(5) 0.2050(2) 0.0396(9) Uani 1 1 d . A .
H10A H 1.2898 0.1734 0.2383 0.047 Uiso 1 1 calc R . .
C11 C 1.1095(3) 0.0605(4) 0.20694(17) 0.0284(7) Uani 1 1 d . . .
C12 C 1.0299(4) 0.1266(5) 0.26127(17) 0.0332(8) Uani 1 1 d . A .
H12A H 0.9317 0.1193 0.2478 0.040 Uiso 1 1 calc R C 3
H12B H 1.0524 0.2514 0.2691 0.040 Uiso 1 1 calc R C 3
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'
Cl Cl 0.1484 0.1585 '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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 N1 164.17(11) . . ?
O1 Ni1 N2 113.20(11) . . ?
N1 Ni1 N2 81.78(11) . . ?
O1 Ni1 Cl2 87.5(5) . . ?
N1 Ni1 Cl2 86.1(5) . . ?
N2 Ni1 Cl2 94.6(4) . . ?
O1 Ni1 Br1 88.34(7) . . ?
N1 Ni1 Br1 93.48(7) . . ?
N2 Ni1 Br1 102.46(7) . . ?
O1 Ni1 Br2 86.0(2) . . ?
N1 Ni1 Br2 87.9(2) . . ?
N2 Ni1 Br2 94.0(2) . . ?
Br1 Ni1 Br2 163.5(2) . . ?
O1 Ni1 Cl1 87.6(3) . . ?
N1 Ni1 Cl1 94.2(3) . . ?
N2 Ni1 Cl1 102.7(4) . . ?
Cl2 Ni1 Cl1 162.6(6) . . ?
C2 N1 C6 120.4(3) . . ?
C2 N1 Ni1 127.1(2) . . ?
C6 N1 Ni1 112.4(2) . . ?
C11 N2 C7 119.8(3) . . ?
C11 N2 Ni1 127.8(2) . . ?
C7 N2 Ni1 111.8(2) . . ?
C2 C1 Cl3 110.0(3) . . ?
C2 C1 Br3 113.4(4) . . ?
N1 C2 C3 120.2(3) . . ?
N1 C2 C1 116.8(3) . . ?
C3 C2 C1 122.9(3) . . ?
C4 C3 C2 119.0(3) . . ?
C5 C4 C3 120.4(3) . . ?
C4 C5 C6 118.9(4) . . ?
N1 C6 C5 121.0(3) . . ?
N1 C6 C7 116.0(3) . . ?
C5 C6 C7 123.0(3) . . ?
N2 C7 C8 120.5(3) . . ?
N2 C7 C6 115.8(3) . . ?
C8 C7 C6 123.6(3) . . ?
C9 C8 C7 119.2(3) . . ?
C10 C9 C8 119.5(3) . . ?
C9 C10 C11 119.6(4) . . ?
N2 C11 C10 121.3(3) . . ?
N2 C11 C12 118.7(3) . . ?
C10 C11 C12 120.0(3) . . ?
C11 C12 Cl4 110.1(3) . . ?
C11 C12 Br4 113.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Ni1 2.4502(7) . ?
Br2 Ni1 2.481(13) . ?
Cl1 Ni1 2.506(16) . ?
Cl2 Ni1 2.34(2) . ?
Br3 C1 1.924(13) . ?
Br4 C12 1.866(6) . ?
Cl3 C1 1.842(9) . ?
Cl4 C12 1.819(6) . ?
Ni1 O1 1.998(2) . ?
Ni1 N1 2.027(2) . ?
Ni1 N2 2.033(3) . ?
N1 C2 1.337(4) . ?
N1 C6 1.358(4) . ?
N2 C11 1.345(4) . ?
N2 C7 1.354(4) . ?
C1 C2 1.502(5) . ?
C2 C3 1.409(5) . ?
C3 C4 1.385(6) . ?
C4 C5 1.358(6) . ?
C5 C6 1.398(4) . ?
C6 C7 1.468(5) . ?
C7 C8 1.399(5) . ?
C8 C9 1.384(6) . ?
C9 C10 1.367(6) . ?
C10 C11 1.390(5) . ?
C11 C12 1.497(5) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Ni1 N1 C2 23.5(5) . . . . ?
N2 Ni1 N1 C2 -174.8(3) . . . . ?
Cl2 Ni1 N1 C2 89.9(5) . . . . ?
Br1 Ni1 N1 C2 -72.7(3) . . . . ?
Br2 Ni1 N1 C2 90.8(3) . . . . ?
Cl1 Ni1 N1 C2 -72.6(4) . . . . ?
O1 Ni1 N1 C6 -152.3(3) . . . . ?
N2 Ni1 N1 C6 9.4(2) . . . . ?
Cl2 Ni1 N1 C6 -85.9(5) . . . . ?
Br1 Ni1 N1 C6 111.46(19) . . . . ?
Br2 Ni1 N1 C6 -85.0(3) . . . . ?
Cl1 Ni1 N1 C6 111.6(4) . . . . ?
O1 Ni1 N2 C11 -9.8(3) . . . . ?
N1 Ni1 N2 C11 175.6(3) . . . . ?
Cl2 Ni1 N2 C11 -99.1(6) . . . . ?
Br1 Ni1 N2 C11 83.8(3) . . . . ?
Br2 Ni1 N2 C11 -97.2(3) . . . . ?
Cl1 Ni1 N2 C11 83.1(4) . . . . ?
O1 Ni1 N2 C7 161.1(2) . . . . ?
N1 Ni1 N2 C7 -13.5(2) . . . . ?
Cl2 Ni1 N2 C7 71.9(6) . . . . ?
Br1 Ni1 N2 C7 -105.3(2) . . . . ?
Br2 Ni1 N2 C7 73.7(3) . . . . ?
Cl1 Ni1 N2 C7 -106.0(4) . . . . ?
C6 N1 C2 C3 -1.5(5) . . . . ?
Ni1 N1 C2 C3 -177.0(2) . . . . ?
C6 N1 C2 C1 176.2(3) . . . . ?
Ni1 N1 C2 C1 0.7(4) . . . . ?
Cl3 C1 C2 N1 122.5(4) . . . . ?
Br3 C1 C2 N1 120.8(4) . . . . ?
Cl3 C1 C2 C3 -59.9(5) . . . . ?
Br3 C1 C2 C3 -61.5(5) . . . . ?
N1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C4 -177.0(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C2 N1 C6 C5 1.3(4) . . . . ?
Ni1 N1 C6 C5 177.4(2) . . . . ?
C2 N1 C6 C7 180.0(3) . . . . ?
Ni1 N1 C6 C7 -3.9(3) . . . . ?
C4 C5 C6 N1 -0.1(5) . . . . ?
C4 C5 C6 C7 -178.7(3) . . . . ?
C11 N2 C7 C8 4.8(4) . . . . ?
Ni1 N2 C7 C8 -166.9(2) . . . . ?
C11 N2 C7 C6 -173.0(3) . . . . ?
Ni1 N2 C7 C6 15.3(3) . . . . ?
N1 C6 C7 N2 -7.8(4) . . . . ?
C5 C6 C7 N2 170.9(3) . . . . ?
N1 C6 C7 C8 174.5(3) . . . . ?
C5 C6 C7 C8 -6.8(5) . . . . ?
N2 C7 C8 C9 -2.3(5) . . . . ?
C6 C7 C8 C9 175.3(3) . . . . ?
C7 C8 C9 C10 -1.3(6) . . . . ?
C8 C9 C10 C11 2.4(6) . . . . ?
C7 N2 C11 C10 -3.8(5) . . . . ?
Ni1 N2 C11 C10 166.5(3) . . . . ?
C7 N2 C11 C12 175.7(3) . . . . ?
Ni1 N2 C11 C12 -14.0(4) . . . . ?
C9 C10 C11 N2 0.1(5) . . . . ?
C9 C10 C11 C12 -179.3(3) . . . . ?
N2 C11 C12 Cl4 104.8(3) . . . . ?
C10 C11 C12 Cl4 -75.8(4) . . . . ?
N2 C11 C12 Br4 103.0(3) . . . . ?
C10 C11 C12 Br4 -77.6(4) . . . . ?
