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#$Date: 2016-03-22 23:48:09 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179078 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/40/4304087.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_4304087
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 Br2.11 Cl1.89 Cu N2, H2 O'
_chemical_formula_sum            'C12 H12 Br2.11 Cl1.89 Cu N2 O'
_chemical_formula_weight         497.83
_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                 92.811(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7776(12)
_cell_length_b                   7.5783(9)
_cell_length_c                   20.600(3)
_cell_measurement_reflns_used    3741
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.35
_cell_volume                     1524.6(3)
_computing_cell_refinement       'Bruker (2002) SMART'
_computing_data_collection       'Bruker (2002) SMART'
_computing_data_reduction        'Bruker (2002) SAINT'
_computing_molecular_graphics    'Bruker (2002) SHELXTL'
_computing_publication_material  'Bruker (2002) SHELXTL'
_computing_structure_refinement  'Bruker (2002) SHELXTL'
_computing_structure_solution    'Bruker (2002) SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9815
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         3772
_exptl_absorpt_coefficient_mu    7.203
_exptl_absorpt_correction_T_max  0.5328
_exptl_absorpt_correction_T_min  0.2212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             961
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0250
_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)+(0.0192P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0484
_refine_ls_wR_factor_ref         0.0499
_reflns_number_gt                2608
_reflns_number_total             3108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic7014786-file003_4.cif
_cod_data_source_block           3
_cod_original_cell_volume        1524.5(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4304087
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
Cu1 Cu 0.85731(3) 0.31923(5) 0.164014(15) 0.01784(12) Uani 1 1 d D . .
Br1 Br 1.06591(5) 0.50337(7) 0.348714(19) 0.0330(2) Uani 0.917(4) 1 d PD A 1
Br2 Br 0.55724(5) 0.26115(6) -0.00874(2) 0.0289(2) Uani 0.894(4) 1 d PD A 1
Br3 Br 0.9480(18) 0.0312(14) 0.1880(9) 0.0122(2) Uiso 0.103(2) 1 d PD B 1
Br4 Br 0.7000(4) 0.5432(4) 0.13267(16) 0.0143(8) Uiso 0.200(3) 1 d PD B 1
Cl1 Cl 1.097(5) 0.523(5) 0.3404(13) 0.10(4) Uiso 0.083(4) 1 d PD A 2
Cl2 Cl 0.574(3) 0.261(4) -0.0054(13) 0.09(3) Uiso 0.106(4) 1 d PD A 2
Cl3 Cl 0.9378(6) 0.0411(5) 0.1892(3) 0.0283(11) Uani 0.897(2) 1 d PD B 2
Cl4 Cl 0.7025(4) 0.5388(4) 0.13358(17) 0.0494(19) Uani 0.800(3) 1 d PD B 2
N1 N 1.0525(2) 0.4664(3) 0.16790(10) 0.0176(5) Uani 1 1 d . A .
N2 N 0.9176(2) 0.2804(3) 0.07378(10) 0.0166(5) Uani 1 1 d . A .
C1 C 1.0283(3) 0.6304(4) 0.26784(12) 0.0238(7) Uani 1 1 d D . .
H1A H 0.9304 0.6169 0.2541 0.029 Uiso 1 1 calc R A 1
H1B H 1.0468 0.7576 0.2748 0.029 Uiso 1 1 calc R A 1
C2 C 1.1149(3) 0.5626(4) 0.21553(13) 0.0198(6) Uani 1 1 d . A .
C3 C 1.2529(3) 0.6018(4) 0.21572(14) 0.0268(7) Uani 1 1 d . . .
H3A H 1.2946 0.6701 0.2500 0.032 Uiso 1 1 calc R A .
C4 C 1.3296(3) 0.5418(4) 0.16626(15) 0.0285(7) Uani 1 1 d . A .
H4A H 1.4251 0.5653 0.1663 0.034 Uiso 1 1 calc R . .
C5 C 1.2654(3) 0.4467(4) 0.11637(14) 0.0239(7) Uani 1 1 d . . .
H5A H 1.3162 0.4042 0.0815 0.029 Uiso 1 1 calc R A .
C6 C 1.1270(3) 0.4141(4) 0.11771(13) 0.0180(6) Uani 1 1 d . A .
C7 C 1.0485(3) 0.3277(4) 0.06308(13) 0.0189(6) Uani 1 1 d . . .
C8 C 1.1025(3) 0.3020(4) 0.00280(13) 0.0229(7) Uani 1 1 d . A .
H8A H 1.1938 0.3369 -0.0045 0.027 Uiso 1 1 calc R . .
C9 C 1.0222(3) 0.2252(4) -0.04663(13) 0.0259(7) Uani 1 1 d . . .
H9A H 1.0575 0.2082 -0.0883 0.031 Uiso 1 1 calc R A .
C10 C 0.8909(3) 0.1736(4) -0.03495(13) 0.0237(7) Uani 1 1 d . A .
H10A H 0.8350 0.1190 -0.0682 0.028 Uiso 1 1 calc R . .
C11 C 0.8413(3) 0.2027(4) 0.02622(13) 0.0209(7) Uani 1 1 d . . .
C12 C 0.7016(3) 0.1390(4) 0.04212(13) 0.0271(7) Uani 1 1 d D A .
H12A H 0.6884 0.1579 0.0890 0.033 Uiso 1 1 calc R C 1
H12B H 0.6949 0.0107 0.0334 0.033 Uiso 1 1 calc R C 1
O1 O 0.7958(2) 0.3317(3) 0.25292(10) 0.0265(5) Uani 1 1 d D B .
H1 H 0.810(4) 0.243(3) 0.2758(14) 0.061(9) Uiso 1 1 d D . .
H2 H 0.728(2) 0.392(4) 0.2622(17) 0.061(9) Uiso 1 1 d D . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
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 Cu1 N2 174.28(9) . . ?
O1 Cu1 N1 104.25(9) . . ?
N2 Cu1 N1 79.30(8) . . ?
O1 Cu1 Cl3 87.15(17) . . ?
N2 Cu1 Cl3 87.82(17) . . ?
N1 Cu1 Cl3 99.75(15) . . ?
O1 Cu1 Cl4 89.54(11) . . ?
N2 Cu1 Cl4 94.17(11) . . ?
N1 Cu1 Cl4 101.48(11) . . ?
Cl3 Cu1 Cl4 158.68(16) . . ?
O1 Cu1 Br4 89.72(10) . . ?
N2 Cu1 Br4 93.99(10) . . ?
N1 Cu1 Br4 101.38(10) . . ?
Cl3 Cu1 Br4 158.76(16) . . ?
O1 Cu1 Br3 88.8(5) . . ?
N2 Cu1 Br3 86.2(5) . . ?
N1 Cu1 Br3 98.2(4) . . ?
Cl4 Cu1 Br3 160.1(4) . . ?
Br4 Cu1 Br3 160.2(4) . . ?
C2 N1 C6 118.3(2) . . ?
C2 N1 Cu1 131.35(18) . . ?
C6 N1 Cu1 108.72(17) . . ?
C11 N2 C7 119.6(2) . . ?
C11 N2 Cu1 124.49(18) . . ?
C7 N2 Cu1 115.80(18) . . ?
C2 C1 Cl1 104.0(16) . . ?
C2 C1 Br1 110.94(19) . . ?
N1 C2 C3 121.8(3) . . ?
N1 C2 C1 117.4(2) . . ?
C3 C2 C1 120.8(3) . . ?
C4 C3 C2 119.7(3) . . ?
C3 C4 C5 118.7(3) . . ?
C6 C5 C4 119.3(3) . . ?
N1 C6 C5 121.9(3) . . ?
N1 C6 C7 115.5(2) . . ?
C5 C6 C7 122.4(2) . . ?
N2 C7 C8 120.8(3) . . ?
N2 C7 C6 116.8(2) . . ?
C8 C7 C6 122.4(3) . . ?
C9 C8 C7 119.4(3) . . ?
C10 C9 C8 119.5(3) . . ?
C9 C10 C11 119.0(3) . . ?
N2 C11 C10 121.8(3) . . ?
N2 C11 C12 117.5(2) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 Cl2 109.2(11) . . ?
C11 C12 Br2 111.89(19) . . ?
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
Cu1 O1 1.958(2) . ?
Cu1 N2 1.999(2) . ?
Cu1 N1 2.209(2) . ?
Cu1 Cl3 2.301(3) . ?
Cu1 Cl4 2.315(3) . ?
Cu1 Br4 2.360(4) . ?
Cu1 Br3 2.398(9) . ?
Br1 C1 1.944(3) . ?
Br2 C12 1.950(3) . ?
Cl1 C1 1.801(10) . ?
Cl2 C12 1.800(10) . ?
N1 C2 1.344(3) . ?
N1 C6 1.353(3) . ?
N2 C11 1.339(3) . ?
N2 C7 1.358(3) . ?
C1 C2 1.494(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.372(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.378(4) . ?
C6 C7 1.483(4) . ?
C7 C8 1.387(3) . ?
C8 C9 1.384(4) . ?
C9 C10 1.374(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.500(4) . ?
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 Cu1 N1 C2 -6.9(3) . . . . ?
N2 Cu1 N1 C2 177.7(3) . . . . ?
Cl3 Cu1 N1 C2 -96.4(3) . . . . ?
Cl4 Cu1 N1 C2 85.6(3) . . . . ?
Br4 Cu1 N1 C2 85.8(3) . . . . ?
Br3 Cu1 N1 C2 -97.7(5) . . . . ?
O1 Cu1 N1 C6 158.09(17) . . . . ?
N2 Cu1 N1 C6 -17.32(17) . . . . ?
Cl3 Cu1 N1 C6 68.6(2) . . . . ?
Cl4 Cu1 N1 C6 -109.44(19) . . . . ?
Br4 Cu1 N1 C6 -109.27(19) . . . . ?
Br3 Cu1 N1 C6 67.3(5) . . . . ?
O1 Cu1 N2 C11 58.4(10) . . . . ?
N1 Cu1 N2 C11 -172.7(2) . . . . ?
Cl3 Cu1 N2 C11 86.9(3) . . . . ?
Cl4 Cu1 N2 C11 -71.8(2) . . . . ?
Br4 Cu1 N2 C11 -71.9(2) . . . . ?
Br3 Cu1 N2 C11 88.2(4) . . . . ?
O1 Cu1 N2 C7 -117.3(9) . . . . ?
N1 Cu1 N2 C7 11.56(18) . . . . ?
Cl3 Cu1 N2 C7 -88.8(2) . . . . ?
Cl4 Cu1 N2 C7 112.5(2) . . . . ?
Br4 Cu1 N2 C7 112.4(2) . . . . ?
Br3 Cu1 N2 C7 -87.5(4) . . . . ?
C6 N1 C2 C3 -2.9(4) . . . . ?
Cu1 N1 C2 C3 160.9(2) . . . . ?
C6 N1 C2 C1 175.5(2) . . . . ?
Cu1 N1 C2 C1 -20.8(4) . . . . ?
Cl1 C1 C2 N1 116.7(17) . . . . ?
Br1 C1 C2 N1 107.7(2) . . . . ?
Cl1 C1 C2 C3 -64.9(17) . . . . ?
Br1 C1 C2 C3 -73.9(3) . . . . ?
N1 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 N1 C6 C5 4.3(4) . . . . ?
Cu1 N1 C6 C5 -162.9(2) . . . . ?
C2 N1 C6 C7 -172.8(2) . . . . ?
Cu1 N1 C6 C7 20.0(3) . . . . ?
C4 C5 C6 N1 -2.7(4) . . . . ?
C4 C5 C6 C7 174.1(3) . . . . ?
C11 N2 C7 C8 2.2(4) . . . . ?
Cu1 N2 C7 C8 178.1(2) . . . . ?
C11 N2 C7 C6 179.7(2) . . . . ?
Cu1 N2 C7 C6 -4.4(3) . . . . ?
N1 C6 C7 N2 -12.0(4) . . . . ?
C5 C6 C7 N2 170.9(3) . . . . ?
N1 C6 C7 C8 165.4(2) . . . . ?
C5 C6 C7 C8 -11.6(4) . . . . ?
N2 C7 C8 C9 -0.8(4) . . . . ?
C6 C7 C8 C9 -178.1(3) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C7 N2 C11 C10 -2.0(4) . . . . ?
Cu1 N2 C11 C10 -177.6(2) . . . . ?
C7 N2 C11 C12 174.9(2) . . . . ?
Cu1 N2 C11 C12 -0.6(4) . . . . ?
C9 C10 C11 N2 0.4(4) . . . . ?
C9 C10 C11 C12 -176.4(3) . . . . ?
N2 C11 C12 Cl2 115.9(11) . . . . ?
C10 C11 C12 Cl2 -67.1(12) . . . . ?
N2 C11 C12 Br2 117.1(2) . . . . ?
C10 C11 C12 Br2 -65.9(3) . . . . ?
