#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/71/2207112.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_2207112
loop_
_publ_author_name
'Reinoso, Santiago'
'Vitoria, Pablo'
'San Felices, Leire'
'Lezama, Luis'
'Gutiérrez-Zorrilla, Juan M.'
_publ_section_title
(2,2'-Bipyridyl-κ²N,N')(chloranilato-κ²O,O')copper(II)
_journal_coeditor_code           YA6258
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1925
_journal_page_last               m1927
_journal_paper_doi               10.1107/S1600536805027649
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu (C6 Cl2 O4) (C10 H8 N2)]'
_chemical_formula_moiety         'C16 H8 Cl2 Cu1 N2 O4'
_chemical_formula_sum            'C16 H8 Cl2 Cu N2 O4'
_chemical_formula_weight         426.68
_chemical_name_systematic
;
(2,2'-Bipyridyl-κ²N,N')(chloranilato-κ²O,O')copper(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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.987(3)
_cell_length_b                   7.4380(10)
_cell_length_c                   17.215(2)
_cell_measurement_reflns_used    6500
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3.5
_cell_volume                     3096.6(7)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF99.2 (Beurskens et al., 1999)'
_diffrn_detector_area_resol_mean '1024 \\times 1024 with blocks 2 \\times 2'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       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  0.045
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14006
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.78
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2003)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.74
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.74
_refine_ls_R_factor_all          0.111
_refine_ls_R_factor_gt           0.035
_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)+(0.0227P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.055
_refine_ls_wR_factor_ref         0.065
_reflns_number_gt                2120
_reflns_number_total             4506
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya6258.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2207112
_cod_database_fobs_code          2207112
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_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
_atom_site_type_symbol
Cu1 0.050506(13) 0.21793(4) 0.02153(2) 0.03594(11) Uani d . 1 Cu
Cl2 -0.12598(3) 0.18923(10) -0.18043(4) 0.0448(2) Uani d . 1 Cl
Cl1 -0.06659(3) 0.51922(10) 0.17048(4) 0.0479(2) Uani d . 1 Cl
O2 -0.01831(6) 0.1861(2) -0.05719(10) 0.0399(5) Uani d . 1 O
O4 -0.20367(7) 0.3575(3) -0.09432(12) 0.0504(6) Uani d . 1 O
O1 0.00710(7) 0.3375(2) 0.08286(10) 0.0402(5) Uani d . 1 O
O3 -0.17809(7) 0.4977(3) 0.05564(12) 0.0516(6) Uani d . 1 O
N12 0.09663(8) 0.1055(3) -0.04055(12) 0.0294(5) Uani d . 1 N
C14 -0.04423(10) 0.3515(3) 0.04461(15) 0.0297(6) Uani d . 1 C
N1 0.12136(8) 0.2463(3) 0.10076(12) 0.0299(5) Uani d . 1 N
C11 0.07935(10) 0.0408(3) -0.11404(16) 0.0345(7) Uani d . 1 C
H11 0.0418 0.0457 -0.1393 0.041 Uiso calc R 1 H
C13 -0.08389(10) 0.4339(3) 0.07398(15) 0.0295(6) Uani d . 1 C
C4 0.22449(11) 0.2563(4) 0.20481(18) 0.0486(8) Uani d . 1 C
H4 0.2593 0.257 0.2406 0.058 Uiso calc R 1 H
C5 0.21735(11) 0.1806(4) 0.13017(17) 0.0411(8) Uani d . 1 C
H5 0.2474 0.133 0.1145 0.049 Uiso calc R 1 H
C9 0.17024(12) -0.0388(4) -0.11707(18) 0.0460(8) Uani d . 1 C
H9 0.1951 -0.0871 -0.1435 0.055 Uiso calc R 1 H
C2 0.12891(11) 0.3214(3) 0.17286(16) 0.0364(7) Uani d . 1 C
H2 0.0985 0.3692 0.1876 0.044 Uiso calc R 1 H
C6 0.16529(10) 0.1756(3) 0.07862(16) 0.0309(6) Uani d . 1 C
C7 0.15100(10) 0.0987(3) -0.00320(16) 0.0292(6) Uani d . 1 C
C17 -0.15539(10) 0.3535(3) -0.05616(16) 0.0318(7) Uani d . 1 C
C18 -0.14057(11) 0.4355(3) 0.03006(17) 0.0337(7) Uani d . 1 C
C10 0.11473(12) -0.0332(4) -0.15452(18) 0.0416(7) Uani d . 1 C
H10 0.1015 -0.0787 -0.2061 0.05 Uiso calc R 1 H
C16 -0.11130(10) 0.2769(3) -0.08430(15) 0.0302(6) Uani d . 1 C
C8 0.18877(11) 0.0272(4) -0.04072(17) 0.0390(7) Uani d . 1 C
H8 0.2262 0.0238 -0.0147 0.047 Uiso calc R 1 H
C3 0.17999(12) 0.3311(4) 0.22641(17) 0.0430(8) Uani d . 1 C
H3 0.1843 0.3869 0.276 0.052 Uiso calc R 1 H
C15 -0.05865(10) 0.2665(3) -0.03730(15) 0.0296(6) Uani d . 1 C
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 0 '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 0.006 '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_publ_flag
O1 Cu1 O2 85.14(7) y
O1 Cu1 N12 177.54(8) y
O2 Cu1 N12 96.23(8) y
O1 Cu1 N1 96.00(8) y
O2 Cu1 N1 178.79(8) y
N12 Cu1 N1 82.65(9) y
C15 O2 Cu1 112.13(15) ?
C14 O1 Cu1 112.63(15) ?
C11 N12 C7 119.4(2) ?
C11 N12 Cu1 125.90(17) ?
C7 N12 Cu1 114.74(17) ?
O1 C14 C13 124.6(2) ?
O1 C14 C15 114.7(2) ?
C13 C14 C15 120.7(2) ?
C2 N1 C6 119.4(2) ?
C2 N1 Cu1 125.93(17) ?
C6 N1 Cu1 114.66(17) ?
N12 C11 C10 122.4(3) ?
N12 C11 H11 118.8 ?
C10 C11 H11 118.8 ?
C14 C13 C18 121.5(2) ?
C14 C13 Cl1 119.4(2) ?
C18 C13 Cl1 118.73(19) ?
C5 C4 C3 119.7(3) ?
C5 C4 H4 120.2 ?
C3 C4 H4 120.2 ?
C4 C5 C6 119.5(3) ?
C4 C5 H5 120.2 ?
C6 C5 H5 120.2 ?
C8 C9 C10 119.8(3) ?
C8 C9 H9 120.1 ?
C10 C9 H9 120.1 ?
N1 C2 C3 122.5(2) ?
N1 C2 H2 118.8 ?
C3 C2 H2 118.8 ?
N1 C6 C5 120.5(2) ?
N1 C6 C7 113.5(2) ?
C5 C6 C7 125.9(2) ?
N12 C7 C8 121.1(2) ?
N12 C7 C6 114.4(2) ?
C8 C7 C6 124.5(2) ?
O4 C17 C16 124.7(3) ?
O4 C17 C18 117.9(2) ?
C16 C17 C18 117.4(2) ?
O3 C18 C13 124.1(3) ?
O3 C18 C17 118.1(2) ?
C13 C18 C17 117.8(2) ?
C11 C10 C9 118.5(3) ?
C11 C10 H10 120.8 ?
C9 C10 H10 120.8 ?
C15 C16 C17 122.2(2) ?
C15 C16 Cl2 119.18(19) ?
C17 C16 Cl2 118.59(19) ?
C9 C8 C7 118.8(3) ?
C9 C8 H8 120.6 ?
C7 C8 H8 120.6 ?
C2 C3 C4 118.3(3) ?
C2 C3 H3 120.8 ?
C4 C3 H3 120.8 ?
O2 C15 C16 124.8(2) ?
O2 C15 C14 115.1(2) ?
C16 C15 C14 120.1(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 1.9128(17) y
Cu1 O2 1.9176(17) y
Cu1 N1 1.956(2) y
Cu1 N12 1.947(2) y
Cl2 C16 1.730(3) ?
Cl1 C13 1.728(3) ?
O2 C15 1.290(3) ?
O4 C17 1.220(3) ?
O1 C14 1.290(3) ?
O3 C18 1.223(3) ?
N12 C11 1.320(3) ?
N12 C7 1.350(3) ?
C14 C13 1.366(3) ?
C14 C15 1.504(3) ?
N1 C2 1.331(3) ?
N1 C6 1.355(3) ?
C11 C10 1.371(3) ?
C11 H11 0.93 ?
C13 C18 1.428(3) ?
C4 C5 1.373(4) ?
C4 C3 1.376(4) ?
C4 H4 0.93 ?
C5 C6 1.378(3) ?
C5 H5 0.93 ?
C9 C8 1.370(4) ?
C9 C10 1.375(3) ?
C9 H9 0.93 ?
C2 C3 1.376(3) ?
C2 H2 0.93 ?
C6 C7 1.478(3) ?
C7 C8 1.378(3) ?
C17 C16 1.429(3) ?
C17 C18 1.561(4) ?
C10 H10 0.93 ?
C16 C15 1.362(3) ?
C8 H8 0.93 ?
C3 H3 0.93 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5 O3 3_545 0.93 2.54 3.465(3) 173 yes
C8 H8 O3 3_545 0.93 2.40 3.330(3) 177 yes
C9 H9 O4 3_545 0.93 2.49 3.171(4) 130 yes
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
O1 Cu1 O2 C15 4.97(17)
N12 Cu1 O2 C15 -172.98(17)
O2 Cu1 O1 C14 -3.75(17)
N1 Cu1 O1 C14 176.66(17)
O2 Cu1 N12 C11 2.1(2)
N1 Cu1 N12 C11 -178.4(2)
O2 Cu1 N12 C7 -179.08(17)
N1 Cu1 N12 C7 0.47(17)
Cu1 O1 C14 C13 -178.7(2)
Cu1 O1 C14 C15 2.0(3)
O1 Cu1 N1 C2 2.5(2)
N12 Cu1 N1 C2 -179.6(2)
O1 Cu1 N1 C6 -179.83(17)
N12 Cu1 N1 C6 -1.90(17)
C7 N12 C11 C10 -0.2(4)
Cu1 N12 C11 C10 178.6(2)
O1 C14 C13 C18 -176.4(2)
C15 C14 C13 C18 2.9(4)
O1 C14 C13 Cl1 -2.8(4)
C15 C14 C13 Cl1 176.45(18)
C3 C4 C5 C6 -2.0(4)
C6 N1 C2 C3 0.2(4)
Cu1 N1 C2 C3 177.82(19)
C2 N1 C6 C5 0.2(4)
Cu1 N1 C6 C5 -177.64(19)
C2 N1 C6 C7 -179.3(2)
Cu1 N1 C6 C7 2.8(3)
C4 C5 C6 N1 0.7(4)
C4 C5 C6 C7 -179.9(3)
C11 N12 C7 C8 0.7(4)
Cu1 N12 C7 C8 -178.3(2)
C11 N12 C7 C6 179.8(2)
Cu1 N12 C7 C6 0.9(3)
N1 C6 C7 N12 -2.5(3)
C5 C6 C7 N12 178.0(2)
N1 C6 C7 C8 176.7(2)
C5 C6 C7 C8 -2.8(4)
C14 C13 C18 O3 175.4(3)
Cl1 C13 C18 O3 1.8(4)
C14 C13 C18 C17 -4.9(4)
Cl1 C13 C18 C17 -178.53(18)
O4 C17 C18 O3 0.9(4)
C16 C17 C18 O3 -178.3(2)
O4 C17 C18 C13 -178.8(2)
C16 C17 C18 C13 2.0(3)
N12 C11 C10 C9 -0.5(4)
C8 C9 C10 C11 0.7(4)
O4 C17 C16 C15 -176.0(2)
C18 C17 C16 C15 3.1(4)
O4 C17 C16 Cl2 2.3(4)
C18 C17 C16 Cl2 -178.59(17)
C10 C9 C8 C7 -0.3(4)
N12 C7 C8 C9 -0.4(4)
C6 C7 C8 C9 -179.5(3)
N1 C2 C3 C4 -1.5(4)
C5 C4 C3 C2 2.4(4)
Cu1 O2 C15 C16 175.3(2)
Cu1 O2 C15 C14 -5.1(3)
C17 C16 C15 O2 174.1(2)
Cl2 C16 C15 O2 -4.1(4)
C17 C16 C15 C14 -5.4(4)
Cl2 C16 C15 C14 176.36(18)
O1 C14 C15 O2 2.2(3)
C13 C14 C15 O2 -177.2(2)
O1 C14 C15 C16 -178.2(2)
C13 C14 C15 C16 2.4(4)
