#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230824.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_2230824
loop_
_publ_author_name
'Ozair, Lailatun Nazirah'
'Abdullah, Norbani'
'Lo, Kong Mun'
_publ_section_title
;
 Bis(4-hydroxybenzoato-κ²O,O')bis(pyridine-κN)copper(II)
;
_journal_coeditor_code           OM2435
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m952
_journal_paper_doi               10.1107/S1600536811023038
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu (C7 H5 O3)2 (C5 H5 N)2]'
_chemical_formula_moiety         'C24 H20 Cu N2 O6'
_chemical_formula_sum            'C24 H20 Cu N2 O6'
_chemical_formula_weight         495.96
_chemical_name_systematic
;
Bis(4-hydroxybenzoato-κ²O,O')bis(pyridine-κN)copper(II)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.1240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6715(2)
_cell_length_b                   8.53850(10)
_cell_length_c                   12.3988(2)
_cell_measurement_reflns_used    4633
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.95
_cell_volume                     1067.41(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9756
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0263
_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)+(0.0301P)²+0.7197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0664
_reflns_number_gt                2202
_reflns_number_total             2448
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            om2435.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230824
_cod_database_fobs_code          2230824
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 1.0000 0.0000 1.0000 0.01147(8) Uani d S 1 2 . .
O O1 0.82299(10) 0.04277(13) 1.01071(9) 0.0143(2) Uani d . 1 1 . .
O O2 0.81152(11) 0.10333(13) 0.83387(9) 0.0162(2) Uani d . 1 1 . .
O O3 0.28650(12) 0.42997(16) 0.85782(10) 0.0258(3) Uani d . 1 1 . .
H H3A 0.2618 0.4788 0.7956 0.039 Uiso calc R 1 1 . .
N N1 1.05579(12) 0.21481(15) 1.06344(11) 0.0139(3) Uani d . 1 1 . .
C C1 0.76211(15) 0.10384(17) 0.91341(13) 0.0138(3) Uani d . 1 1 . .
C C2 0.63226(15) 0.18074(17) 0.89663(13) 0.0152(3) Uani d . 1 1 . .
C C3 0.56256(16) 0.24646(19) 0.79114(14) 0.0181(3) Uani d . 1 1 . .
H H3 0.5956 0.2350 0.7291 0.022 Uiso calc R 1 1 . .
C C4 0.44571(16) 0.32832(19) 0.77537(14) 0.0191(3) Uani d . 1 1 . .
H H4 0.3985 0.3717 0.7028 0.023 Uiso calc R 1 1 . .
C C5 0.39815(16) 0.3465(2) 0.86627(14) 0.0193(3) Uani d . 1 1 . .
C C6 0.46532(18) 0.2783(2) 0.97123(15) 0.0270(4) Uani d . 1 1 . .
H H6 0.4314 0.2881 1.0328 0.032 Uiso calc R 1 1 . .
C C7 0.58159(17) 0.1960(2) 0.98591(14) 0.0232(4) Uani d . 1 1 . .
H H7 0.6271 0.1496 1.0577 0.028 Uiso calc R 1 1 . .
C C8 1.01481(17) 0.27077(19) 1.14781(14) 0.0188(3) Uani d . 1 1 . .
H H8 0.9540 0.2105 1.1719 0.023 Uiso calc R 1 1 . .
C C9 1.05787(19) 0.4126(2) 1.20074(15) 0.0242(4) Uani d . 1 1 . .
H H9 1.0285 0.4478 1.2611 0.029 Uiso calc R 1 1 . .
C C10 1.14449(18) 0.50256(19) 1.16446(15) 0.0226(3) Uani d . 1 1 . .
H H10 1.1758 0.6003 1.1996 0.027 Uiso calc R 1 1 . .
C C11 1.18455(16) 0.4474(2) 1.07611(15) 0.0205(3) Uani d . 1 1 . .
H H11 1.2425 0.5076 1.0485 0.025 Uiso calc R 1 1 . .
C C12 1.13899(15) 0.30311(18) 1.02847(14) 0.0170(3) Uani d . 1 1 . .
H H12 1.1678 0.2651 0.9685 0.020 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
_geom_angle_publ_flag
O1 Cu1 O1 . 3_757 180.0 ?
O1 Cu1 N1 . 3_757 91.60(5) ?
O1 Cu1 N1 . . 88.40(5) ?
O1 Cu1 N1 3_757 . 91.60(5) ?
N1 Cu1 N1 3_757 . 180.0 ?
O1 Cu1 O2 . . 57.60(4) ?
O1 Cu1 O2 3_757 . 122.40(4) ?
N1 Cu1 O2 3_757 . 86.83(4) ?
N1 Cu1 O2 . . 93.17(4) ?
C1 O1 Cu1 . . 102.35(9) ?
C1 O2 Cu1 . . 77.78(8) ?
C5 O3 H3A . . 109.5 ?
C12 N1 C8 . . 118.01(13) ?
C12 N1 Cu1 . . 122.01(10) ?
C8 N1 Cu1 . . 119.89(10) ?
O2 C1 O1 . . 121.52(14) ?
O2 C1 C2 . . 120.11(14) ?
O1 C1 C2 . . 118.34(13) ?
C7 C2 C3 . . 118.88(14) ?
C7 C2 C1 . . 121.28(14) ?
C3 C2 C1 . . 119.75(14) ?
C4 C3 C2 . . 120.95(15) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 119.55(15) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
O3 C5 C4 . . 122.64(15) ?
O3 C5 C6 . . 117.43(15) ?
C4 C5 C6 . . 119.94(15) ?
C7 C6 C5 . . 120.02(15) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 120.61(15) ?
C6 C7 H7 . . 119.7 ?
C2 C7 H7 . . 119.7 ?
N1 C8 C9 . . 122.52(15) ?
N1 C8 H8 . . 118.7 ?
C9 C8 H8 . . 118.7 ?
C8 C9 C10 . . 119.02(15) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C11 C10 C9 . . 118.72(15) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C10 C11 C12 . . 119.01(15) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
N1 C12 C11 . . 122.69(15) ?
N1 C12 H12 . . 118.7 ?
C11 C12 H12 . . 118.7 ?
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
Cu1 O1 . 1.9706(10) ?
Cu1 N1 . 2.0076(13) ?
Cu1 O2 . 2.5204(11) ?
O1 C1 . 1.2790(19) ?
O2 C1 . 1.2614(18) ?
O3 C5 . 1.3624(19) ?
O3 H3A . 0.8400 ?
N1 C12 . 1.340(2) ?
N1 C8 . 1.347(2) ?
C1 C2 . 1.485(2) ?
C2 C7 . 1.388(2) ?
C2 C3 . 1.393(2) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.388(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.391(2) ?
C6 C7 . 1.385(2) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.382(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.386(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.383(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
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
O3 H3A O2 2_656 0.84 1.87 2.7028(16) 171
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 Cu1 O1 C1 3_757 . . . -10E1(5) ?
N1 Cu1 O1 C1 3_757 . . . -90.19(9) ?
N1 Cu1 O1 C1 . . . . 89.81(9) ?
O2 Cu1 O1 C1 . . . . -4.95(8) ?
O1 Cu1 O2 C1 . . . . 5.02(8) ?
O1 Cu1 O2 C1 3_757 . . . -174.98(8) ?
N1 Cu1 O2 C1 3_757 . . . 98.93(9) ?
N1 Cu1 O2 C1 . . . . -81.07(9) ?
O1 Cu1 N1 C12 . . . . -143.73(12) ?
O1 Cu1 N1 C12 3_757 . . . 36.27(12) ?
N1 Cu1 N1 C12 3_757 . . . 0E1(10) ?
O2 Cu1 N1 C12 . . . . -86.30(12) ?
O1 Cu1 N1 C8 . . . . 39.72(12) ?
O1 Cu1 N1 C8 3_757 . . . -140.28(12) ?
N1 Cu1 N1 C8 3_757 . . . 0E1(10) ?
O2 Cu1 N1 C8 . . . . 97.15(12) ?
Cu1 O2 C1 O1 . . . . -7.68(13) ?
Cu1 O2 C1 C2 . . . . 170.43(13) ?
Cu1 O1 C1 O2 . . . . 9.84(16) ?
Cu1 O1 C1 C2 . . . . -168.30(11) ?
O2 C1 C2 C7 . . . . -173.84(15) ?
O1 C1 C2 C7 . . . . 4.3(2) ?
O2 C1 C2 C3 . . . . 2.7(2) ?
O1 C1 C2 C3 . . . . -179.10(14) ?
C7 C2 C3 C4 . . . . 1.1(2) ?
C1 C2 C3 C4 . . . . -175.51(14) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C3 C4 C5 O3 . . . . 177.74(15) ?
C3 C4 C5 C6 . . . . -2.2(3) ?
O3 C5 C6 C7 . . . . -178.07(17) ?
C4 C5 C6 C7 . . . . 1.9(3) ?
C5 C6 C7 C2 . . . . 0.0(3) ?
C3 C2 C7 C6 . . . . -1.5(3) ?
C1 C2 C7 C6 . . . . 175.12(17) ?
C12 N1 C8 C9 . . . . -1.7(2) ?
Cu1 N1 C8 C9 . . . . 175.01(13) ?
N1 C8 C9 C10 . . . . 1.3(3) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C9 C10 C11 C12 . . . . -1.2(3) ?
C8 N1 C12 C11 . . . . 0.6(2) ?
Cu1 N1 C12 C11 . . . . -176.06(12) ?
C10 C11 C12 N1 . . . . 0.9(3) ?
