#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/59/2235933.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_2235933
loop_
_publ_author_name
'Qi, Jin-li'
'Xu, Wei'
_publ_section_title
;
 (2,2'-Bipyridine-κ²N,N')bis(4-formylbenzoato-κO¹)copper(II)
;
_journal_coeditor_code           NK2165
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1062
_journal_page_last               m1063
_journal_paper_doi               10.1107/S1600536812031066
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C8 H5 O3)2 (C10 H8 N2)]'
_chemical_formula_moiety         'C26 H18 Cu N2 O6'
_chemical_formula_sum            'C26 H18 Cu N2 O6'
_chemical_formula_weight         517.96
_chemical_name_systematic
;
(2,2'-Bipyridine-κ²N,N')bis(4-formylbenzoato-
κO¹)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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.11(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.923(2)
_cell_length_b                   10.992(2)
_cell_length_c                   18.275(4)
_cell_measurement_reflns_used    11333
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.19
_cell_volume                     2357.9(8)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_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  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11333
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.161
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0582
_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)+(0.0500P)²+1.7765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                1672
_reflns_number_total             2700
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2165.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235933
_cod_database_fobs_code          2235933
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
_atom_site_symmetry_multiplicity
Cu Cu 0.5000 0.53295(6) 0.7500 0.0500(3) Uani d S 1 2
O O1 0.4216(2) 0.4112(2) 0.79856(15) 0.0620(7) Uani d . 1 1
O O2 0.5705(2) 0.4465(3) 0.88645(15) 0.0660(8) Uani d . 1 1
O O3 0.3550(4) -0.0045(4) 1.1014(2) 0.1132(14) Uani d . 1 1
C C1 0.4812(3) 0.3924(3) 0.8630(2) 0.0505(9) Uani d . 1 1
C C2 0.4358(3) 0.2966(3) 0.9090(2) 0.0496(9) Uani d . 1 1
C C3 0.3319(3) 0.2404(3) 0.8846(2) 0.0571(10) Uani d . 1 1
H H3A 0.2888 0.2623 0.8391 0.069 Uiso calc R 1 1
C C4 0.2918(4) 0.1529(3) 0.9271(2) 0.0606(11) Uani d . 1 1
H H4A 0.2221 0.1158 0.9099 0.073 Uiso calc R 1 1
C C5 0.3537(4) 0.1197(4) 0.9947(2) 0.0597(10) Uani d . 1 1
C C6 0.4576(4) 0.1749(5) 1.0194(3) 0.0834(15) Uani d . 1 1
H H6A 0.5006 0.1522 1.0648 0.100 Uiso calc R 1 1
C C7 0.4980(4) 0.2632(4) 0.9774(2) 0.0752(13) Uani d . 1 1
H H7A 0.5674 0.3007 0.9950 0.090 Uiso calc R 1 1
C C8 0.3097(5) 0.0272(4) 1.0403(3) 0.0819(14) Uani d . 1 1
H H8A 0.2411 -0.0099 1.0203 0.098 Uiso calc R 1 1
N N 0.5875(3) 0.6702(3) 0.71745(17) 0.0516(8) Uani d . 1 1
C C9 0.5513(3) 0.7822(3) 0.73221(19) 0.0499(9) Uani d . 1 1
C C10 0.6077(3) 0.8850(4) 0.7152(2) 0.0607(11) Uani d . 1 1
H H10A 0.5824 0.9618 0.7261 0.073 Uiso calc R 1 1
C C11 0.7018(4) 0.8726(4) 0.6819(2) 0.0677(12) Uani d . 1 1
H H11A 0.7411 0.9411 0.6704 0.081 Uiso calc R 1 1
C C12 0.7375(4) 0.7592(5) 0.6655(2) 0.0700(12) Uani d . 1 1
H H12A 0.8003 0.7493 0.6422 0.084 Uiso calc R 1 1
C C13 0.6783(3) 0.6600(4) 0.6844(2) 0.0619(11) Uani d . 1 1
H H13A 0.7025 0.5827 0.6737 0.074 Uiso calc R 1 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'
O O 0.0106 0.0060 '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'
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
O1 Cu O1 2_656 . 92.48(17)
O1 Cu N 2_656 . 93.83(12)
O1 Cu N . . 170.15(12)
O1 Cu N 2_656 2_656 170.15(12)
O1 Cu N . 2_656 93.83(12)
N Cu N . 2_656 80.96(18)
C1 O1 Cu . . 107.4(2)
O2 C1 O1 . . 123.3(4)
O2 C1 C2 . . 121.3(4)
O1 C1 C2 . . 115.5(3)
C3 C2 C7 . . 118.6(4)
C3 C2 C1 . . 121.4(3)
C7 C2 C1 . . 120.0(3)
C4 C3 C2 . . 120.7(4)
C4 C3 H3A . . 119.6
C2 C3 H3A . . 119.6
C5 C4 C3 . . 120.6(4)
C5 C4 H4A . . 119.7
C3 C4 H4A . . 119.7
C4 C5 C6 . . 119.1(4)
C4 C5 C8 . . 120.4(4)
C6 C5 C8 . . 120.5(4)
C7 C6 C5 . . 120.6(4)
C7 C6 H6A . . 119.7
C5 C6 H6A . . 119.7
C6 C7 C2 . . 120.4(4)
C6 C7 H7A . . 119.8
C2 C7 H7A . . 119.8
O3 C8 C5 . . 125.5(5)
O3 C8 H8A . . 117.3
C5 C8 H8A . . 117.3
C13 N C9 . . 118.8(3)
C13 N Cu . . 125.7(3)
C9 N Cu . . 115.5(3)
N C9 C10 . . 121.2(4)
N C9 C9 . 2_656 113.9(2)
C10 C9 C9 . 2_656 124.9(2)
C11 C10 C9 . . 119.2(4)
C11 C10 H10A . . 120.4
C9 C10 H10A . . 120.4
C12 C11 C10 . . 119.8(4)
C12 C11 H11A . . 120.1
C10 C11 H11A . . 120.1
C11 C12 C13 . . 118.3(4)
C11 C12 H12A . . 120.8
C13 C12 H12A . . 120.8
N C13 C12 . . 122.7(4)
N C13 H13A . . 118.6
C12 C13 H13A . . 118.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu O1 2_656 1.935(3) y
Cu O1 . 1.935(3) y
Cu N . 1.984(3) y
Cu N 2_656 1.984(3) y
O1 C1 . 1.282(4) ?
O2 C1 . 1.229(4) ?
O3 C8 . 1.203(6) ?
C1 C2 . 1.505(5) ?
C2 C3 . 1.386(5) ?
C2 C7 . 1.386(5) ?
C3 C4 . 1.374(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.373(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.382(6) ?
C5 C8 . 1.469(6) ?
C6 C7 . 1.376(6) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
N C13 . 1.334(5) ?
N C9 . 1.347(4) ?
C9 C10 . 1.378(5) ?
C9 C9 2_656 1.482(7) ?
C10 C11 . 1.374(6) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.367(6) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.375(6) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
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
C4 H4A O2 3_445 0.93 2.58 3.460(5) 159
C13 H13A O3 8_555 0.93 2.58 3.284(6) 133
