#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/28/8102864.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102864
loop_
_publ_author_name
'Xiao-Ling Li'
'Guang-Zhen Liu'
_publ_section_title
;
 Crystal structure of bis(hydrogen
 2,3-quinolinedicarboxylato)copper(II), Cu(C11H6NO4)2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              761
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C22 H12 Cu N2 O8'
_chemical_formula_weight         495.88
_chemical_name_systematic
;
[Cu(C11H6NO4)2]
;
_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                 115.8900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6992(14)
_cell_length_b                   5.8010(7)
_cell_length_c                   13.5977(15)
_cell_measurement_reflns_used    4200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.92
_cell_volume                     901.18(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6488
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.274
_exptl_absorpt_correction_T_max  0.8031
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0244
_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)+(0.0370P)²+0.7173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                1542
_reflns_number_total             1668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3212.cff
_cod_data_source_block           b
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8102864
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 1.0000 0.0000 0.02278(13) Uani 1 2 d S . .
O1 O 0.08521(12) 1.2741(2) 0.06280(10) 0.0269(3) Uani 1 1 d . . .
O2 O 0.16721(13) 1.4838(2) 0.21399(11) 0.0258(3) Uani 1 1 d . . .
O3 O 0.31580(11) 1.2771(2) 0.42064(11) 0.0258(3) Uani 1 1 d . . .
H3 H 0.3145 1.1807 0.3760 0.039 Uiso 1 1 calc R . .
O4 O 0.18895(13) 1.4356(3) 0.47155(12) 0.0349(4) Uani 1 1 d . . .
N1 N 0.00494(13) 0.9709(3) 0.15798(13) 0.0192(3) Uani 1 1 d . . .
C1 C 0.07883(15) 1.1285(3) 0.22264(14) 0.0185(4) Uani 1 1 d . . .
C2 C 0.11626(15) 1.1391(3) 0.33710(14) 0.0205(4) Uani 1 1 d . . .
C3 C 0.06852(18) 0.9838(3) 0.38207(16) 0.0246(4) Uani 1 1 d . . .
H3A H 0.0908 0.9869 0.4569 0.030 Uiso 1 1 calc R . .
C4 C -0.01372(16) 0.8197(3) 0.31661(15) 0.0222(4) Uani 1 1 d . . .
C5 C -0.06600(17) 0.6585(4) 0.36023(16) 0.0269(4) Uani 1 1 d . . .
H5 H -0.0485 0.6641 0.4341 0.032 Uiso 1 1 calc R . .
C6 C -0.14143(19) 0.4960(3) 0.29536(18) 0.0296(5) Uani 1 1 d . . .
H6 H -0.1756 0.3917 0.3247 0.035 Uiso 1 1 calc R . .
C7 C -0.16762(19) 0.4860(4) 0.18358(19) 0.0306(5) Uani 1 1 d . . .
H7 H -0.2175 0.3714 0.1402 0.037 Uiso 1 1 calc R . .
C8 C -0.12135(18) 0.6414(4) 0.13720(16) 0.0278(4) Uani 1 1 d . . .
H8 H -0.1415 0.6340 0.0628 0.033 Uiso 1 1 calc R . .
C9 C -0.04294(15) 0.8129(3) 0.20270(15) 0.0201(4) Uani 1 1 d . . .
C10 C 0.11494(15) 1.3093(3) 0.16333(15) 0.0199(4) Uani 1 1 d . . .
C11 C 0.20851(16) 1.3036(3) 0.41312(14) 0.0217(4) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 3_575 . ?
O1 Cu1 N1 98.45(6) 3_575 . ?
O1 Cu1 N1 81.55(6) . . ?
O1 Cu1 N1 81.55(6) 3_575 3_575 ?
O1 Cu1 N1 98.45(6) . 3_575 ?
N1 Cu1 N1 180.00(8) . 3_575 ?
C10 O1 Cu1 117.54(12) . . ?
C11 O3 H3 109.5 . . ?
C1 N1 C9 119.01(15) . . ?
C1 N1 Cu1 108.30(11) . . ?
C9 N1 Cu1 132.34(12) . . ?
N1 C1 C2 123.88(16) . . ?
N1 C1 C10 114.54(15) . . ?
C2 C1 C10 121.47(16) . . ?
C3 C2 C1 117.42(17) . . ?
C3 C2 C11 118.09(16) . . ?
C1 C2 C11 124.44(16) . . ?
C2 C3 C4 120.91(17) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 122.38(17) . . ?
C3 C4 C9 118.38(17) . . ?
C5 C4 C9 119.23(18) . . ?
C6 C5 C4 120.80(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.77(18) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 121.53(19) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.88(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C8 120.96(16) . . ?
N1 C9 C4 120.28(17) . . ?
C8 C9 C4 118.76(17) . . ?
O2 C10 O1 124.47(17) . . ?
O2 C10 C1 118.90(16) . . ?
O1 C10 C1 116.58(16) . . ?
O4 C11 O3 121.47(18) . . ?
O4 C11 C2 121.99(17) . . ?
O3 C11 C2 116.15(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9031(14) 3_575 ?
Cu1 O1 1.9031(14) . ?
Cu1 N1 2.1282(15) . ?
Cu1 N1 2.1282(15) 3_575 ?
O1 C10 1.266(2) . ?
O2 C10 1.241(2) . ?
O3 C11 1.330(2) . ?
O3 H3 0.8200 . ?
O4 C11 1.205(2) . ?
N1 C1 1.330(2) . ?
N1 C9 1.379(2) . ?
C1 C2 1.416(2) . ?
C1 C10 1.511(2) . ?
C2 C3 1.370(3) . ?
C2 C11 1.515(3) . ?
C3 C4 1.406(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.418(3) . ?
C4 C9 1.427(3) . ?
C5 C6 1.359(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(3) . ?
C8 H8 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.76 2.5762(19) 171.9 2_545
O3 H3 O1 0.82 2.64 3.146(2) 121.7 2_545
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cu1 O1 C10 -115(100) 3_575 . . . ?
N1 Cu1 O1 C10 5.67(14) . . . . ?
N1 Cu1 O1 C10 -174.33(14) 3_575 . . . ?
O1 Cu1 N1 C1 169.60(12) 3_575 . . . ?
O1 Cu1 N1 C1 -10.40(12) . . . . ?
N1 Cu1 N1 C1 50.9(8) 3_575 . . . ?
O1 Cu1 N1 C9 -3.23(17) 3_575 . . . ?
O1 Cu1 N1 C9 176.77(17) . . . . ?
N1 Cu1 N1 C9 -121.9(8) 3_575 . . . ?
C9 N1 C1 C2 2.9(3) . . . . ?
Cu1 N1 C1 C2 -171.02(14) . . . . ?
C9 N1 C1 C10 -173.21(15) . . . . ?
Cu1 N1 C1 C10 12.85(18) . . . . ?
N1 C1 C2 C3 -3.3(3) . . . . ?
C10 C1 C2 C3 172.56(17) . . . . ?
N1 C1 C2 C11 174.20(17) . . . . ?
C10 C1 C2 C11 -9.9(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C11 C2 C3 C4 -177.18(17) . . . . ?
C2 C3 C4 C5 -179.15(19) . . . . ?
C2 C3 C4 C9 2.4(3) . . . . ?
C3 C4 C5 C6 -177.19(19) . . . . ?
C9 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
C6 C7 C8 C9 1.7(3) . . . . ?
C1 N1 C9 C8 -179.63(17) . . . . ?
Cu1 N1 C9 C8 -7.4(3) . . . . ?
C1 N1 C9 C4 0.2(3) . . . . ?
Cu1 N1 C9 C4 172.44(13) . . . . ?
C7 C8 C9 N1 179.88(19) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C3 C4 C9 N1 -2.8(3) . . . . ?
C5 C4 C9 N1 178.67(17) . . . . ?
C3 C4 C9 C8 177.04(18) . . . . ?
C5 C4 C9 C8 -1.5(3) . . . . ?
Cu1 O1 C10 O2 -177.52(14) . . . . ?
Cu1 O1 C10 C1 -0.2(2) . . . . ?
N1 C1 C10 O2 167.94(16) . . . . ?
C2 C1 C10 O2 -8.3(3) . . . . ?
N1 C1 C10 O1 -9.6(2) . . . . ?
C2 C1 C10 O1 174.19(17) . . . . ?
C3 C2 C11 O4 -59.0(3) . . . . ?
C1 C2 C11 O4 123.5(2) . . . . ?
C3 C2 C11 O3 113.9(2) . . . . ?
C1 C2 C11 O3 -63.6(2) . . . . ?
