#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:18:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179623 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/87/4508799.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508799
loop_
_publ_author_name
'Meng, Wen-Li'
'Liu, Guang-Xiang'
'Okamura, Taka-aki'
'Kawaguchi, Hiroyuki'
'Zhang, Zheng-Hua'
'Sun, Wei-Yin'
'Ueyama, Norikazu'
_publ_section_title
;
 Syntheses, Crystal Structures, and Magnetic Properties of Novel
 Copper(II) Complexes with the Flexible Bidentate Ligand
 1-Bromo-3,5-bis(imidazol-1-ylmethyl)benzene
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2092
_journal_paper_doi               10.1021/cg060304i
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C28 H28 Br2 Cl2 Cu N8 O '
_chemical_formula_sum            'C28 H28 Br2 Cl2 Cu N8 O'
_chemical_formula_weight         786.84
_chemical_name_systematic
; 
[Cu(bib)2]Cl2-H2O 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             'Wed May  4 13:45:51 2005'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.39(3)
_cell_angle_beta                 86.47(4)
_cell_angle_gamma                88.22(4)
_cell_formula_units_Z            1
_cell_length_a                   8.952(13)
_cell_length_b                   9.096(10)
_cell_length_c                   10.114(12)
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      3.1
_cell_volume                     812.5(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1387
_diffrn_reflns_av_sigmaI/netI    0.5858
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6031
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    3.331
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             393
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.769
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      0.782
_refine_ls_R_factor_all          0.2760
_refine_ls_R_factor_gt           0.0615
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                563
_reflns_number_total             2836
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg060304isup1.cif
_cod_data_source_block           2
_cod_database_code               4508799
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br -0.32803(16) 0.40258(18) 0.36261(14) 0.1061(7) Uani 1 1 d .
Cu1 Cu 0.5000 0.0000 0.0000 0.0938(10) Uani 1 2 d S
Cl1 Cl 0.5421(5) 0.3031(4) -0.1327(4) 0.070(2) Uani 0.618(3) 1 d PU
Cl2 Cl 0.0584(10) 0.4910(14) 0.0166(12) 0.065(5) Uani 0.382(3) 1 d PU
O1 O 0.3033(16) 0.5173(14) 0.9805(13) 0.097(5) Uani 0.50 1 d PU
N11 N 0.3219(11) 0.2059(13) 0.3193(11) 0.069(4) Uani 1 1 d U
N12 N 0.4207(10) 0.0732(12) 0.1722(10) 0.074(4) Uani 1 1 d U
N31 N 0.0839(12) 0.0895(13) 0.8481(10) 0.059(4) Uani 1 1 d U
N32 N 0.2968(11) 0.0033(14) 0.9274(10) 0.072(4) Uani 1 1 d U
C1 C 0.1201(13) 0.3189(12) 0.4516(12) 0.044(4) Uani 1 1 d U
C2 C 0.1089(12) 0.2661(11) 0.5874(12) 0.074(5) Uani 1 1 d U
H1 H 0.1961 0.2420 0.6359 0.089 Uiso 1 1 calc R
C3 C -0.0332(14) 0.2493(12) 0.6512(12) 0.049(4) Uani 1 1 d U
C4 C -0.1602(13) 0.2936(13) 0.5832(12) 0.062(4) Uani 1 1 d U
H2 H -0.2542 0.2896 0.6324 0.074 Uiso 1 1 calc R
C5 C -0.1573(13) 0.3401(14) 0.4561(14) 0.070(5) Uani 1 1 d U
C6 C -0.0121(14) 0.3544(12) 0.3792(11) 0.072(4) Uani 1 1 d U
H3 H -0.0063 0.3859 0.2851 0.087 Uiso 1 1 calc R
C11 C 0.2664(10) 0.3444(10) 0.3774(9) 0.062(4) Uani 1 1 d U
H4 H 0.3403 0.3710 0.4383 0.075 Uiso 1 1 calc R
H5 H 0.2569 0.4287 0.3039 0.075 Uiso 1 1 calc R
C12 C 0.3585(11) 0.2057(13) 0.1895(12) 0.069(4) Uani 1 1 d U
H6 H 0.3431 0.2865 0.1202 0.083 Uiso 1 1 calc R
C13 C 0.4179(13) -0.0046(13) 0.2998(16) 0.084(5) Uani 1 1 d U
H7 H 0.4552 -0.1038 0.3199 0.100 Uiso 1 1 calc R
C14 C 0.3571(14) 0.0734(16) 0.3934(12) 0.087(5) Uani 1 1 d U
H8 H 0.3425 0.0435 0.4873 0.104 Uiso 1 1 calc R
C31 C -0.0360(11) 0.1883(12) 0.8005(12) 0.066(4) Uani 1 1 d U
H9 H -0.0384 0.2741 0.8504 0.079 Uiso 1 1 calc R
H10 H -0.1311 0.1355 0.8245 0.079 Uiso 1 1 calc R
C32 C 0.2030(16) 0.1073(15) 0.9096(11) 0.061(4) Uani 1 1 d U
H11 H 0.2188 0.1987 0.9409 0.073 Uiso 1 1 calc R
C33 C 0.2338(16) -0.1128(15) 0.8704(12) 0.083(6) Uani 1 1 d U
H12 H 0.2768 -0.2082 0.8628 0.100 Uiso 1 1 calc R
C34 C 0.1043(17) -0.0600(14) 0.8310(11) 0.072(5) Uani 1 1 d U
H13 H 0.0327 -0.1158 0.7953 0.087 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 '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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
N32 Cu1 N32 180.0 1_554 2_656
N32 Cu1 N12 93.3(4) 1_554 .
N32 Cu1 N12 86.7(4) 2_656 .
N32 Cu1 N12 86.7(4) 1_554 2_655
N32 Cu1 N12 93.3(4) 2_656 2_655
N12 Cu1 N12 180.0 . 2_655
C12 N11 C14 111.5(10) . .
C12 N11 C11 123.4(12) . .
C14 N11 C11 124.7(11) . .
C12 N12 C13 103.5(9) . .
C12 N12 Cu1 129.2(10) . .
C13 N12 Cu1 127.2(10) . .
C32 N31 C34 99.9(11) . .
C32 N31 C31 133.3(14) . .
C34 N31 C31 126.7(13) . .
C32 N32 C33 104.0(12) . .
C32 N32 Cu1 129.5(12) . 1_556
C33 N32 Cu1 126.1(10) . 1_556
C2 C1 C6 120.3(11) . .
C2 C1 C11 121.8(11) . .
C6 C1 C11 117.8(11) . .
C1 C2 C3 118.4(12) . .
C1 C2 H1 120.8 . .
C3 C2 H1 120.8 . .
C4 C3 C2 121.0(12) . .
C4 C3 C31 123.6(12) . .
C2 C3 C31 115.2(11) . .
C5 C4 C3 123.2(12) . .
C5 C4 H2 118.4 . .
C3 C4 H2 118.4 . .
C4 C5 C6 119.2(12) . .
C4 C5 Br1 123.8(11) . .
C6 C5 Br1 116.8(11) . .
C1 C6 C5 117.4(11) . .
C1 C6 H3 121.3 . .
C5 C6 H3 121.3 . .
C1 C11 N11 110.9(8) . .
C1 C11 H4 109.5 . .
N11 C11 H4 109.5 . .
C1 C11 H5 109.5 . .
N11 C11 H5 109.5 . .
H4 C11 H5 108.1 . .
N11 C12 N12 109.3(11) . .
N11 C12 H6 125.4 . .
N12 C12 H6 125.4 . .
C14 C13 N12 113.5(11) . .
C14 C13 H7 123.3 . .
N12 C13 H7 123.3 . .
C13 C14 N11 102.2(12) . .
C13 C14 H8 128.9 . .
N11 C14 H8 128.9 . .
N31 C31 C3 118.2(9) . .
N31 C31 H9 107.8 . .
C3 C31 H9 107.8 . .
N31 C31 H10 107.8 . .
C3 C31 H10 107.8 . .
H9 C31 H10 107.1 . .
N32 C32 N31 119.2(13) . .
N32 C32 H11 120.4 . .
N31 C32 H11 120.4 . .
C34 C33 N32 105.1(13) . .
C34 C33 H12 127.5 . .
N32 C33 H12 127.5 . .
C33 C34 N31 111.5(14) . .
C33 C34 H13 124.3 . .
N31 C34 H13 124.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C5 1.875(12) .
Cu1 N32 2.001(11) 1_554
Cu1 N32 2.001(11) 2_656
Cu1 N12 2.036(8) .
Cu1 N12 2.036(8) 2_655
Cl2 Cl2 1.118(15) 2_565
N11 C12 1.334(11) .
N11 C14 1.359(12) .
N11 C11 1.526(10) .
N12 C12 1.342(10) .
N12 C13 1.375(11) .
N31 C32 1.294(12) .
N31 C34 1.401(12) .
N31 C31 1.437(11) .
N32 C32 1.245(12) .
N32 C33 1.423(13) .
N32 Cu1 2.001(11) 1_556
C1 C2 1.384(12) .
C1 C6 1.433(13) .
C1 C11 1.476(11) .
C2 C3 1.392(12) .
C2 H1 0.9500 .
C3 C4 1.384(12) .
C3 C31 1.527(12) .
C4 C5 1.290(13) .
C4 H2 0.9500 .
C5 C6 1.473(13) .
C6 H3 0.9500 .
C11 H4 0.9900 .
C11 H5 0.9900 .
C12 H6 0.9500 .
C13 C14 1.345(12) .
C13 H7 0.9500 .
C14 H8 0.9500 .
C31 H9 0.9900 .
C31 H10 0.9900 .
C32 H11 0.9500 .
C33 C34 1.303(13) .
C33 H12 0.9500 .
C34 H13 0.9500 .
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
N32 Cu1 N12 C12 -66.7(11) 1_554
N32 Cu1 N12 C12 113.3(11) 2_656
N32 Cu1 N12 C13 112.8(11) 1_554
N32 Cu1 N12 C13 -67.2(11) 2_656
C6 C1 C2 C3 -0.3(17) .
C11 C1 C2 C3 178.0(9) .
C1 C2 C3 C4 -4.4(17) .
C1 C2 C3 C31 179.1(9) .
C2 C3 C4 C5 6.3(19) .
C31 C3 C4 C5 -177.5(11) .
C3 C4 C5 C6 -3(2) .
C3 C4 C5 Br1 -179.3(9) .
C2 C1 C6 C5 3.2(17) .
C11 C1 C6 C5 -175.1(9) .
C4 C5 C6 C1 -1.6(17) .
Br1 C5 C6 C1 174.9(8) .
C2 C1 C11 N11 91.0(13) .
C6 C1 C11 N11 -90.6(12) .
C12 N11 C11 C1 124.3(12) .
C14 N11 C11 C1 -64.0(15) .
C14 N11 C12 N12 -0.5(15) .
C11 N11 C12 N12 172.3(9) .
C13 N12 C12 N11 0.2(13) .
Cu1 N12 C12 N11 179.8(7) .
C12 N12 C13 C14 0.1(15) .
Cu1 N12 C13 C14 -179.4(8) .
N12 C13 C14 N11 -0.4(16) .
C12 N11 C14 C13 0.5(16) .
C11 N11 C14 C13 -172.1(9) .
C32 N31 C31 C3 101.2(15) .
C34 N31 C31 C3 -74.9(14) .
C4 C3 C31 N31 153.5(11) .
C2 C3 C31 N31 -30.0(14) .
C33 N32 C32 N31 -1.1(17) .
Cu1 N32 C32 N31 172.9(8) 1_556
C34 N31 C32 N32 4.1(16) .
C31 N31 C32 N32 -172.8(11) .
C32 N32 C33 C34 -2.7(15) .
Cu1 N32 C33 C34 -176.9(8) 1_556
N32 C33 C34 N31 5.3(15) .
C32 N31 C34 C33 -5.6(14) .
C31 N31 C34 C33 171.5(11) .
