#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/98/2209826.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_2209826
loop_
_publ_author_name
'He, Hong-Shan'
_publ_section_title
;
 Bis[μ-2-(1H-imidazol-2-yl)phenolato]bis[chloromethanolcopper(II)]
;
_journal_coeditor_code           ER2011
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1782
_journal_page_last               m1783
_journal_paper_doi               10.1107/S1600536806022720
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu2 (C9 H7 N2 O1)2 Cl2 (C1 H4 O)2]'
_chemical_formula_moiety         'C20 H22 Cl2 Cu2 N4 O4'
_chemical_formula_sum            'C20 H22 Cl2 Cu2 N4 O4'
_chemical_formula_weight         580.40
_chemical_name_systematic
;
Bis[μ-2-(1H-imidazol-2-yl)phenolato]bis[chloromethanolcopper(II)]
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 127.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.574(4)
_cell_length_b                   8.4773(17)
_cell_length_c                   16.859(3)
_cell_measurement_reflns_used    5448
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.48
_cell_volume                     2344.6(12)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker 1K CCD'
_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  0.0877
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17383
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  0.8193
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            Dark_brown
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.541
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0222P)²+5.6781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                1483
_reflns_number_total             2539
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2011.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209826
_cod_database_fobs_code          2209826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cu Cu 0.03051(2) 0.64757(6) 0.18804(3) 0.03663(16) Uani d . 1
Cl Cl -0.03280(5) 0.74339(15) 0.03230(7) 0.0493(3) Uani d . 1
O O1 0.06888(13) 0.6041(3) 0.32379(16) 0.0413(7) Uani d . 1
N N1 0.13764(16) 0.7297(4) 0.2396(2) 0.0376(8) Uani d . 1
N N2 0.2685(2) 0.7691(4) 0.3409(3) 0.0427(9) Uani d . 1
C C1 0.1603(2) 0.8283(5) 0.1949(3) 0.0486(11) Uani d . 1
H H1 0.1251 0.8709 0.1314 0.058 Uiso calc R 1
C C2 0.2412(2) 0.8533(5) 0.2575(3) 0.0495(11) Uani d . 1
H H2 0.2722 0.9152 0.2461 0.059 Uiso calc R 1
C C3 0.2053(2) 0.6971(5) 0.3302(3) 0.0354(10) Uani d . 1
C C4 0.2124(2) 0.5981(4) 0.4048(2) 0.0333(9) Uani d . 1
C C5 0.1445(2) 0.5547(5) 0.4004(2) 0.0350(9) Uani d . 1
C C6 0.1552(2) 0.4603(5) 0.4743(3) 0.0428(10) Uani d . 1
H H6 0.1101 0.4301 0.4707 0.051 Uiso calc R 1
C C7 0.2317(3) 0.4100(5) 0.5533(3) 0.0505(11) Uani d . 1
H H7 0.2380 0.3470 0.6026 0.061 Uiso calc R 1
C C8 0.2988(2) 0.4535(5) 0.5588(3) 0.0533(12) Uani d . 1
H H8 0.3505 0.4204 0.6122 0.064 Uiso calc R 1
C C9 0.2896(2) 0.5452(5) 0.4861(3) 0.0445(10) Uani d . 1
H H9 0.3353 0.5732 0.4905 0.053 Uiso calc R 1
H H_N 0.313(2) 0.772(5) 0.387(3) 0.045(13) Uiso d . 1
O O2 0.0581(2) 0.4000(4) 0.1557(3) 0.0581(10) Uani d . 1
C C10 0.0585(4) 0.2547(7) 0.1948(4) 0.0839(17) Uani d . 1
H H10A 0.0694 0.2706 0.2582 0.126 Uiso calc R 1
H H10B 0.1000 0.1887 0.2029 0.126 Uiso calc R 1
H H10C 0.0063 0.2049 0.1502 0.126 Uiso calc R 1
H H_O 0.046(3) 0.391(6) 0.107(3) 0.060(18) Uiso d . 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'
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'
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'
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
N1 Cu O1 . . 89.79(12)
N1 Cu O1 . 2 160.20(11)
O1 Cu O1 . 2 75.15(11)
N1 Cu Cl . . 95.37(10)
O1 Cu Cl . . 165.82(8)
O1 Cu Cl 2 . 96.56(8)
N1 Cu O2 . . 93.27(13)
O1 Cu O2 . . 96.99(12)
O1 Cu O2 2 . 101.14(12)
Cl Cu O2 . . 95.90(9)
N1 Cu Cu . 2 121.54(9)
O1 Cu Cu . 2 39.80(7)
O1 Cu Cu 2 2 39.50(7)
Cl Cu Cu . 2 127.92(4)
O2 Cu Cu . 2 115.15(9)
C5 O1 Cu . . 126.4(2)
C5 O1 Cu . 2 132.9(2)
Cu O1 Cu . 2 100.70(10)
C3 N1 C1 . . 106.7(3)
C3 N1 Cu . . 123.7(3)
C1 N1 Cu . . 129.6(2)
C3 N2 C2 . . 109.7(3)
C3 N2 H_N . . 128(3)
C2 N2 H_N . . 122(3)
C2 C1 N1 . . 109.4(3)
C2 C1 H1 . . 125.3
N1 C1 H1 . . 125.3
C1 C2 N2 . . 105.7(4)
C1 C2 H2 . . 127.1
N2 C2 H2 . . 127.1
N1 C3 N2 . . 108.4(3)
N1 C3 C4 . . 127.2(3)
N2 C3 C4 . . 124.4(3)
C5 C4 C9 . . 118.1(3)
C5 C4 C3 . . 122.1(3)
C9 C4 C3 . . 119.8(3)
O1 C5 C6 . . 120.2(3)
O1 C5 C4 . . 120.3(3)
C6 C5 C4 . . 119.5(3)
C7 C6 C5 . . 121.2(4)
C7 C6 H6 . . 119.4
C5 C6 H6 . . 119.4
C8 C7 C6 . . 119.7(4)
C8 C7 H7 . . 120.2
C6 C7 H7 . . 120.2
C9 C8 C7 . . 120.1(4)
C9 C8 H8 . . 119.9
C7 C8 H8 . . 119.9
C8 C9 C4 . . 121.4(4)
C8 C9 H9 . . 119.3
C4 C9 H9 . . 119.3
C10 O2 Cu . . 128.3(3)
C10 O2 H_O . . 110(4)
Cu O2 H_O . . 114(4)
O2 C10 H10A . . 109.5
O2 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
O2 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu N1 . 1.946(3)
Cu O1 . 1.954(2)
Cu O1 2 1.966(2)
Cu Cl . 2.2633(13)
Cu O2 . 2.323(3)
Cu Cu 2 3.0176(10)
O1 C5 . 1.357(4)
O1 Cu 2 1.966(2)
N1 C3 . 1.335(4)
N1 C1 . 1.382(5)
N2 C3 . 1.345(5)
N2 C2 . 1.361(5)
N2 H_N . 0.76(4)
C1 C2 . 1.345(5)
C1 H1 . 0.9300
C2 H2 . 0.9300
C3 C4 . 1.444(5)
C4 C5 . 1.402(5)
C4 C9 . 1.405(5)
C5 C6 . 1.382(5)
C6 C7 . 1.379(5)
C6 H6 . 0.9300
C7 C8 . 1.375(6)
C7 H7 . 0.9300
C8 C9 . 1.365(6)
C8 H8 . 0.9300
C9 H9 . 0.9300
O2 C10 . 1.394(6)
O2 H_O . 0.70(4)
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 Cu O1 C5 . . -35.9(3)
O1 Cu O1 C5 2 . 157.1(3)
Cl Cu O1 C5 . . -147.4(3)
O2 Cu O1 C5 . . 57.4(3)
Cu Cu O1 C5 2 . 178.9(4)
N1 Cu O1 Cu . 2 145.27(14)
O1 Cu O1 Cu 2 2 -21.74(16)
Cl Cu O1 Cu . 2 33.7(4)
O2 Cu O1 Cu . 2 -121.46(13)
O1 Cu N1 C3 . . 19.7(3)
O1 Cu N1 C3 2 . 59.6(5)
Cl Cu N1 C3 . . -173.5(3)
O2 Cu N1 C3 . . -77.3(3)
Cu Cu N1 C3 2 . 45.1(3)
O1 Cu N1 C1 . . -160.1(3)
O1 Cu N1 C1 2 . -120.2(4)
Cl Cu N1 C1 . . 6.6(3)
O2 Cu N1 C1 . . 102.9(3)
Cu Cu N1 C1 2 . -134.8(3)
C3 N1 C1 C2 . . 0.9(5)
Cu N1 C1 C2 . . -179.2(3)
N1 C1 C2 N2 . . 0.2(5)
C3 N2 C2 C1 . . -1.2(5)
C1 N1 C3 N2 . . -1.7(4)
Cu N1 C3 N2 . . 178.5(3)
C1 N1 C3 C4 . . -179.8(4)
Cu N1 C3 C4 . . 0.3(5)
C2 N2 C3 N1 . . 1.8(5)
C2 N2 C3 C4 . . -180.0(4)
N1 C3 C4 C5 . . -16.7(6)
N2 C3 C4 C5 . . 165.4(4)
N1 C3 C4 C9 . . 164.6(4)
N2 C3 C4 C9 . . -13.3(6)
Cu O1 C5 C6 . . -149.4(3)
Cu O1 C5 C6 2 . 29.1(5)
Cu O1 C5 C4 . . 30.3(5)
Cu O1 C5 C4 2 . -151.2(3)
C9 C4 C5 O1 . . 179.4(3)
C3 C4 C5 O1 . . 0.7(5)
C9 C4 C5 C6 . . -1.0(5)
C3 C4 C5 C6 . . -179.7(4)
O1 C5 C6 C7 . . -179.3(4)
C4 C5 C6 C7 . . 1.0(6)
C5 C6 C7 C8 . . -0.3(6)
C6 C7 C8 C9 . . -0.4(7)
C7 C8 C9 C4 . . 0.4(7)
C5 C4 C9 C8 . . 0.2(6)
C3 C4 C9 C8 . . 179.0(4)
N1 Cu O2 C10 . . 119.6(4)
O1 Cu O2 C10 . . 29.4(4)
O1 Cu O2 C10 2 . -46.8(4)
Cl Cu O2 C10 . . -144.7(4)
Cu Cu O2 C10 2 . -7.7(4)
