#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/31/2233197.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_2233197
loop_
_publ_author_name
'Shi, Fengjuan'
'Deng, Jiguang'
'Dai, Hongxing'
_publ_section_title
;
 Diaquabis(4-hydroxy-5-nitropyridine-2-carboxylato-κ²N¹,O²)copper(II)
;
_journal_coeditor_code           HY2493
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m46
_journal_paper_doi               10.1107/S1600536811052949
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C6 H3 N2 O5)2 (H2 O)2]'
_chemical_formula_moiety         'C12 H10 Cu N4 O12'
_chemical_formula_sum            'C12 H10 Cu N4 O12'
_chemical_formula_weight         465.79
_chemical_name_systematic
;
Diaquabis(4-hydroxy-5-nitropyridine-2-carboxylato-
κ²N¹,O²)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.86(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5327(7)
_cell_length_b                   9.7963(10)
_cell_length_c                   12.2562(12)
_cell_measurement_reflns_used    3085
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.1
_cell_volume                     764.68(15)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9563
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    1.515
_exptl_absorpt_correction_T_max  0.8632
_exptl_absorpt_correction_T_min  0.7515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.494
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1829
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0292
_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)+(0.0360P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                1466
_reflns_number_total             1829
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2493.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2233197
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 Cu1 0.0000 0.5000 0.5000 0.01573(13) Uani d S 1 2
O O1 0.0540(2) 0.53885(14) 0.66132(12) 0.0145(3) Uani d . 1 1
O O2 0.1475(2) 0.70789(14) 0.78407(11) 0.0150(3) Uani d . 1 1
O O3 0.3093(2) 1.08681(14) 0.52856(13) 0.0144(3) Uani d . 1 1
H H3 0.331(5) 1.107(3) 0.592(2) 0.058(11) Uiso d . 1 1
O O4 0.2830(3) 1.07679(17) 0.31323(14) 0.0291(4) Uani d . 1 1
O O5 0.0819(3) 0.9216(2) 0.22215(13) 0.0408(5) Uani d . 1 1
O O6 0.3578(3) 0.40247(18) 0.52615(15) 0.0253(4) Uani d D 1 1
H H6A 0.371(5) 0.381(3) 0.5936(10) 0.060(11) Uiso d D 1 1
H H6B 0.454(7) 0.455(5) 0.516(3) 0.06(2) Uiso d PD 0.50 1
H H6C 0.348(10) 0.332(3) 0.484(3) 0.09(3) Uiso d PD 0.50 1
N N1 0.1030(3) 0.68775(16) 0.49202(13) 0.0113(4) Uani d . 1 1
C C1 0.1142(3) 0.6591(2) 0.68823(16) 0.0121(4) Uani d . 1 1
C C2 0.1493(3) 0.7498(2) 0.59364(16) 0.0108(4) Uani d . 1 1
C C3 0.2222(3) 0.8799(2) 0.61022(16) 0.0109(4) Uani d . 1 1
H H3A 0.2576 0.9169 0.6837 0.013 Uiso calc R 1 1
C C4 0.2450(3) 0.9596(2) 0.51800(17) 0.0106(4) Uani d . 1 1
C C5 0.1881(3) 0.8957(2) 0.41301(16) 0.0114(4) Uani d . 1 1
C C6 0.1219(3) 0.7610(2) 0.40323(16) 0.0119(4) Uani d . 1 1
H H6 0.0891 0.7197 0.3313 0.014 Uiso calc R 1 1
N N2 0.1874(3) 0.97025(17) 0.30795(15) 0.0150(4) Uani d . 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 Cu1 O1 . 3_566 180.0
O1 Cu1 N1 . . 83.24(6)
O1 Cu1 N1 3_566 . 96.76(6)
O1 Cu1 N1 . 3_566 96.76(6)
O1 Cu1 N1 3_566 3_566 83.24(6)
N1 Cu1 N1 . 3_566 180.0
O1 Cu1 O6 . . 89.52(6)
O1 Cu1 O6 . 3_566 90.48(6)
N1 Cu1 O6 . 3_566 87.50(7)
O6 Cu1 N1 . . 92.50(7)
O6 Cu1 O6 . 3_566 180.00
C1 O1 Cu1 . . 114.76(13)
C4 O3 H3 . . 109(2)
H6A O6 H6B . . 112.7(17)
H6A O6 H6C . . 111.5(17)
H6B O6 H6C . . 111.2(17)
C6 N1 C2 . . 117.79(17)
C6 N1 Cu1 . . 129.69(14)
C2 N1 Cu1 . . 112.42(13)
O2 C1 O1 . . 125.79(19)
O2 C1 C2 . . 118.24(17)
O1 C1 C2 . . 115.97(17)
N1 C2 C3 . . 123.75(18)
N1 C2 C1 . . 113.45(17)
C3 C2 C1 . . 122.80(18)
C2 C3 C4 . . 119.73(18)
C2 C3 H3A . . 120.1
C4 C3 H3A . . 120.1
O3 C4 C5 . . 121.85(18)
O3 C4 C3 . . 122.42(18)
C5 C4 C3 . . 115.70(18)
C6 C5 C4 . . 121.20(18)
C6 C5 N2 . . 117.04(17)
C4 C5 N2 . . 121.71(17)
N1 C6 C5 . . 121.74(18)
N1 C6 H6 . . 119.1
C5 C6 H6 . . 119.1
O4 N2 O5 . . 124.71(18)
O4 N2 C5 . . 118.54(17)
O5 N2 C5 . . 116.68(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 N1 1.9685(16)
Cu1 O1 1.9667(15)
Cu1 O6 2.479(2)
O1 C1 1.263(2)
O2 C1 1.242(2)
O3 C4 1.312(2)
O3 H3 0.79(3)
O4 N2 1.211(2)
O5 N2 1.219(2)
O6 H6A 0.840(10)
O6 H6B 0.850(10)
O6 H6C 0.850(10)
N1 C6 1.332(2)
N1 C2 1.358(2)
C1 C2 1.518(3)
C2 C3 1.360(3)
C3 C4 1.409(3)
C3 H3A 0.9500
C4 C5 1.405(3)
C5 C6 1.385(3)
C5 N2 1.480(2)
C6 H6 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 H3 O2 2_556 0.79(3) 1.79(3) 2.544(2) 160(3)
O6 H6A O2 2_546 0.840(10) 2.28(2) 3.014(2) 146(3)
O6 H6B O6 3_666 0.850(10) 2.000(10) 2.836(3) 170(5)
O6 H6C O3 1_545 0.850(10) 2.49(3) 3.109(2) 130(3)
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
N1 Cu1 O1 C1 . 3.72(14)
N1 Cu1 O1 C1 3_566 -176.28(14)
O1 Cu1 N1 C6 . -178.60(18)
O1 Cu1 N1 C6 3_566 1.40(18)
O1 Cu1 N1 C2 . -2.41(13)
O1 Cu1 N1 C2 3_566 177.59(13)
Cu1 O1 C1 O2 . 176.32(16)
Cu1 O1 C1 C2 . -4.1(2)
C6 N1 C2 C3 . -3.0(3)
Cu1 N1 C2 C3 . -179.66(16)
C6 N1 C2 C1 . 177.69(16)
Cu1 N1 C2 C1 . 1.0(2)
O2 C1 C2 N1 . -178.33(17)
O1 C1 C2 N1 . 2.1(3)
O2 C1 C2 C3 . 2.3(3)
O1 C1 C2 C3 . -177.27(18)
N1 C2 C3 C4 . 2.6(3)
C1 C2 C3 C4 . -178.09(18)
C2 C3 C4 O3 . 178.19(18)
C2 C3 C4 C5 . 0.1(3)
O3 C4 C5 C6 . 179.52(18)
C3 C4 C5 C6 . -2.4(3)
O3 C4 C5 N2 . -3.1(3)
C3 C4 C5 N2 . 175.00(17)
C2 N1 C6 C5 . 0.5(3)
Cu1 N1 C6 C5 . 176.56(14)
C4 C5 C6 N1 . 2.1(3)
N2 C5 C6 N1 . -175.38(17)
C6 C5 N2 O4 . -165.03(19)
C4 C5 N2 O4 . 17.5(3)
C6 C5 N2 O5 . 18.0(3)
C4 C5 N2 O5 . -159.5(2)
