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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/4/30/40/4304088.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_4304088
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 Br2.09 Cl1.91 Cu N2'
_chemical_formula_sum            'C12 H10 Br2.09 Cl1.91 Cu N2'
_chemical_formula_weight         480.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.701(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2944(6)
_cell_length_b                   17.1836(15)
_cell_length_c                   11.8504(10)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.71
_cell_measurement_theta_min      2.37
_cell_volume                     1478.0(2)
_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 0.996
_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  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15416
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  430
_diffrn_standards_number         2950
_exptl_absorpt_coefficient_mu    7.445
_exptl_absorpt_correction_T_max  0.7550
_exptl_absorpt_correction_T_min  0.1547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             922
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0165P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0565
_reflns_number_gt                2216
_reflns_number_total             3007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic7014786-file003_5.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4304088
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.24935(7) 0.90951(3) 0.80497(4) 0.03051(16) Uani 1 1 d D . .
Br1 Br 0.0731(13) 0.7465(8) 0.9002(10) 0.0376(19) Uani 0.276(3) 1 d PD A 1
Br2 Br 0.4443(5) 1.1090(3) 0.5367(4) 0.0348(9) Uani 0.351(4) 1 d PD A 1
Br3 Br 0.01968(9) 0.89057(4) 0.65536(7) 0.0340(3) Uani 0.840(7) 1 d PD B 1
Br4 Br 0.4965(9) 0.8308(4) 0.7644(5) 0.0335(8) Uani 0.625(3) 1 d PD B 1
Cl1 Cl 0.0844(12) 0.7464(6) 0.9091(9) 0.0398(19) Uani 0.724(3) 1 d PD A 2
Cl2 Cl 0.4390(9) 1.1036(4) 0.5427(6) 0.080(4) Uani 0.649(4) 1 d PD A 2
Cl3 Cl 0.025(3) 0.8847(16) 0.6675(18) 0.10(3) Uiso 0.160(7) 1 d PD B 2
Cl4 Cl 0.475(3) 0.8292(14) 0.765(2) 0.032(3) Uani 0.375(3) 1 d PD B 2
N1 N 0.2588(4) 0.91483(17) 0.9749(2) 0.0253(7) Uani 1 1 d . A .
N2 N 0.2534(4) 1.02668(16) 0.8199(3) 0.0257(7) Uani 1 1 d . A .
C1 C 0.2776(5) 0.7740(2) 1.0052(3) 0.0378(10) Uani 1 1 d D . .
H1A H 0.2860 0.7371 1.0697 0.045 Uiso 1 1 calc R A 1
H1B H 0.3925 0.7695 0.9677 0.045 Uiso 1 1 calc R A 1
C2 C 0.2605(5) 0.8550(2) 1.0489(3) 0.0285(9) Uani 1 1 d . A .
C3 C 0.2500(5) 0.8673(2) 1.1640(3) 0.0350(10) Uani 1 1 d . . .
H3A H 0.2546 0.8245 1.2149 0.042 Uiso 1 1 calc R A .
C4 C 0.2329(5) 0.9417(2) 1.2037(3) 0.0340(10) Uani 1 1 d . A .
H4A H 0.2241 0.9506 1.2821 0.041 Uiso 1 1 calc R . .
C5 C 0.2287(5) 1.0037(2) 1.1290(3) 0.0312(10) Uani 1 1 d . . .
H5A H 0.2166 1.0555 1.1552 0.037 Uiso 1 1 calc R A .
C6 C 0.2425(4) 0.9887(2) 1.0150(3) 0.0243(9) Uani 1 1 d . A .
C7 C 0.2425(5) 1.0507(2) 0.9276(3) 0.0259(9) Uani 1 1 d . . .
C8 C 0.2341(5) 1.1293(2) 0.9542(3) 0.0334(10) Uani 1 1 d . A .
H8A H 0.2255 1.1458 1.0300 0.040 Uiso 1 1 calc R . .
C9 C 0.2385(5) 1.1838(2) 0.8666(4) 0.0371(10) Uani 1 1 d . . .
H9A H 0.2281 1.2379 0.8815 0.044 Uiso 1 1 calc R A .
C10 C 0.2579(5) 1.1579(2) 0.7595(4) 0.0375(11) Uani 1 1 d . A .
H10A H 0.2662 1.1945 0.7001 0.045 Uiso 1 1 calc R . .
C11 C 0.2656(5) 1.0795(2) 0.7365(3) 0.0292(9) Uani 1 1 d . . .
C12 C 0.2854(6) 1.0478(2) 0.6195(3) 0.0449(12) Uani 1 1 d D A .
H12A H 0.1621 1.0454 0.5763 0.054 Uiso 1 1 calc R C 1
H12B H 0.3343 0.9941 0.6266 0.054 Uiso 1 1 calc R C 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'
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
N1 Cu1 N2 82.42(12) . . ?
N1 Cu1 Cl3 133.6(7) . . ?
N2 Cu1 Cl3 104.9(7) . . ?
N1 Cu1 Cl4 106.8(7) . . ?
N2 Cu1 Cl4 128.9(8) . . ?
Cl3 Cu1 Cl4 103.2(10) . . ?
N1 Cu1 Br3 135.79(9) . . ?
N2 Cu1 Br3 102.02(9) . . ?
Cl4 Cu1 Br3 103.9(7) . . ?
N1 Cu1 Br4 106.35(18) . . ?
N2 Cu1 Br4 126.1(2) . . ?
Cl3 Cu1 Br4 105.3(7) . . ?
Br3 Cu1 Br4 105.79(17) . . ?
C2 N1 C6 118.5(3) . . ?
C2 N1 Cu1 127.8(2) . . ?
C6 N1 Cu1 113.3(2) . . ?
C7 N2 C11 120.0(3) . . ?
C7 N2 Cu1 112.7(2) . . ?
C11 N2 Cu1 127.3(3) . . ?
C2 C1 Cl1 112.3(5) . . ?
C2 C1 Br1 111.7(5) . . ?
N1 C2 C3 121.5(3) . . ?
N1 C2 C1 118.7(3) . . ?
C3 C2 C1 119.7(4) . . ?
C4 C3 C2 119.6(4) . . ?
C3 C4 C5 119.6(4) . . ?
C4 C5 C6 118.8(4) . . ?
N1 C6 C5 121.9(3) . . ?
N1 C6 C7 114.7(3) . . ?
C5 C6 C7 123.4(3) . . ?
N2 C7 C8 121.2(3) . . ?
N2 C7 C6 116.3(3) . . ?
C8 C7 C6 122.4(4) . . ?
C7 C8 C9 118.5(4) . . ?
C10 C9 C8 118.9(4) . . ?
C9 C10 C11 120.9(4) . . ?
N2 C11 C10 120.4(4) . . ?
N2 C11 C12 116.7(3) . . ?
C10 C11 C12 123.0(4) . . ?
C11 C12 Cl2 113.3(4) . . ?
C11 C12 Br2 113.1(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
Cu1 N1 2.011(3) . ?
Cu1 N2 2.021(3) . ?
Cu1 Cl3 2.232(10) . ?
Cu1 Cl4 2.238(10) . ?
Cu1 Br3 2.3379(8) . ?
Cu1 Br4 2.342(3) . ?
Br1 C1 1.904(8) . ?
Br2 C12 1.907(6) . ?
Cl1 C1 1.786(7) . ?
Cl2 C12 1.790(7) . ?
N1 C2 1.350(4) . ?
N1 C6 1.365(4) . ?
N2 C7 1.351(4) . ?
N2 C11 1.352(4) . ?
C1 C2 1.495(5) . ?
C2 C3 1.390(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.389(5) . ?
C6 C7 1.486(5) . ?
C7 C8 1.391(5) . ?
C8 C9 1.400(5) . ?
C9 C10 1.365(5) . ?
C10 C11 1.377(5) . ?
C11 C12 1.510(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
N2 Cu1 N1 C2 179.7(3) . . . . ?
Cl3 Cu1 N1 C2 76.3(11) . . . . ?
Cl4 Cu1 N1 C2 -51.8(9) . . . . ?
Br3 Cu1 N1 C2 80.2(3) . . . . ?
Br4 Cu1 N1 C2 -54.8(4) . . . . ?
N2 Cu1 N1 C6 6.8(2) . . . . ?
Cl3 Cu1 N1 C6 -96.6(10) . . . . ?
Cl4 Cu1 N1 C6 135.3(9) . . . . ?
Br3 Cu1 N1 C6 -92.6(2) . . . . ?
Br4 Cu1 N1 C6 132.3(3) . . . . ?
N1 Cu1 N2 C7 -5.8(2) . . . . ?
Cl3 Cu1 N2 C7 127.4(8) . . . . ?
Cl4 Cu1 N2 C7 -111.3(9) . . . . ?
Br3 Cu1 N2 C7 129.5(2) . . . . ?
Br4 Cu1 N2 C7 -110.6(3) . . . . ?
N1 Cu1 N2 C11 174.0(3) . . . . ?
Cl3 Cu1 N2 C11 -52.8(8) . . . . ?
Cl4 Cu1 N2 C11 68.5(9) . . . . ?
Br3 Cu1 N2 C11 -50.7(3) . . . . ?
Br4 Cu1 N2 C11 69.3(4) . . . . ?
C6 N1 C2 C3 -1.4(5) . . . . ?
Cu1 N1 C2 C3 -173.9(3) . . . . ?
C6 N1 C2 C1 179.8(3) . . . . ?
Cu1 N1 C2 C1 7.2(5) . . . . ?
Cl1 C1 C2 N1 -64.4(6) . . . . ?
Br1 C1 C2 N1 -63.0(6) . . . . ?
Cl1 C1 C2 C3 116.7(6) . . . . ?
Br1 C1 C2 C3 118.1(6) . . . . ?
N1 C2 C3 C4 1.6(6) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C2 N1 C6 C5 0.3(5) . . . . ?
Cu1 N1 C6 C5 173.9(3) . . . . ?
C2 N1 C6 C7 179.8(3) . . . . ?
Cu1 N1 C6 C7 -6.6(4) . . . . ?
C4 C5 C6 N1 0.4(5) . . . . ?
C4 C5 C6 C7 -179.0(3) . . . . ?
C11 N2 C7 C8 3.3(5) . . . . ?
Cu1 N2 C7 C8 -176.8(3) . . . . ?
C11 N2 C7 C6 -175.9(3) . . . . ?
Cu1 N2 C7 C6 4.0(4) . . . . ?
N1 C6 C7 N2 1.7(5) . . . . ?
C5 C6 C7 N2 -178.8(3) . . . . ?
N1 C6 C7 C8 -177.5(3) . . . . ?
C5 C6 C7 C8 1.9(6) . . . . ?
N2 C7 C8 C9 -0.5(5) . . . . ?
C6 C7 C8 C9 178.7(3) . . . . ?
C7 C8 C9 C10 -2.5(6) . . . . ?
C8 C9 C10 C11 2.6(6) . . . . ?
C7 N2 C11 C10 -3.2(5) . . . . ?
Cu1 N2 C11 C10 176.9(3) . . . . ?
C7 N2 C11 C12 177.5(3) . . . . ?
Cu1 N2 C11 C12 -2.4(5) . . . . ?
C9 C10 C11 N2 0.2(6) . . . . ?
C9 C10 C11 C12 179.5(4) . . . . ?
N2 C11 C12 Cl2 -141.7(4) . . . . ?
C10 C11 C12 Cl2 39.0(6) . . . . ?
N2 C11 C12 Br2 -143.2(3) . . . . ?
C10 C11 C12 Br2 37.5(5) . . . . ?
