#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/83/2218328.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_2218328
loop_
_publ_author_name
'Martins, Nuno D.'
'Ramos Silva, Manuela'
'Silva, Joana A.'
'Matos Beja, Ana'
'Sobral, Abilio J. F.N.'
_publ_section_title
;(Benzoato-κ²O,O')(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic
 acid-κ²N,O)copper(II)
;
_journal_coeditor_code           BT2705
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m829
_journal_page_last               m830
_journal_paper_doi               10.1107/S1600536808014268
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C10 H6 N O2) (C7 H5 O2) (C10 H7 N O2)]'
_chemical_formula_moiety         'C27 H18 Cu N2 O6'
_chemical_formula_sum            'C27 H18 Cu N2 O6'
_chemical_formula_weight         529.97
_chemical_name_systematic
;
(Benzoato-κ²O,O')(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic
acid-κ²N,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'
_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                 118.7880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.1140(9)
_cell_length_b                   11.4665(5)
_cell_length_c                   12.1885(8)
_cell_measurement_reflns_used    4050
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7853
_cell_measurement_theta_min      3.2429
_cell_volume                     2341.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0122
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27106
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0368
_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)+(0.0492P)²+2.1952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2536
_reflns_number_total             2928
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2705.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2218328
_cod_database_fobs_code          2218328
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
Cu Cu1 0.5000 0.31494(3) 0.2500 0.04408(13) Uani d S 1
O O1 0.51571(18) 0.1520(3) 0.3083(3) 0.0467(7) Uani d P 0.50
O O2 0.47650(18) 0.1264(3) 0.1065(3) 0.0517(7) Uani d P 0.50
C C1 0.4960(2) 0.0874(4) 0.2116(3) 0.0406(9) Uani d P 0.50
O O3 0.49011(9) 0.42154(18) 0.10765(18) 0.0766(6) Uani d . 1
H H1 0.5218 0.4412 0.0837 0.115 Uiso calc PR 0.50
O O4 0.39680(14) 0.5024(3) -0.0713(3) 0.1504(15) Uani d . 1
N N1 0.37963(10) 0.34319(16) 0.15664(16) 0.0460(4) Uani d . 1
C C2 0.5000 -0.0419(3) 0.2500 0.0568(8) Uani d S 1
C C3 0.50955(16) -0.1029(3) 0.3531(2) 0.0671(7) Uani d . 1
H H3 0.5165 -0.0628 0.4239 0.080 Uiso calc R 1
C C4 0.50904(19) -0.2216(3) 0.3528(3) 0.0774(8) Uani d . 1
H H4 0.5149 -0.2620 0.4228 0.093 Uiso calc R 1
C C5 0.5000 -0.2814(3) 0.2500 0.0767(11) Uani d S 1
H H5 0.5000 -0.3625 0.2500 0.092 Uiso calc SR 1
C C6 0.41763(13) 0.4477(2) 0.0220(2) 0.0563(5) Uani d . 1
C C7 0.35528(12) 0.40982(19) 0.05672(19) 0.0492(5) Uani d . 1
C C8 0.27586(13) 0.4476(2) -0.0157(2) 0.0631(6) Uani d . 1
H H8 0.2609 0.4935 -0.0865 0.076 Uiso calc R 1
C C9 0.22163(14) 0.4154(3) 0.0204(3) 0.0690(7) Uani d . 1
H H9 0.1688 0.4392 -0.0260 0.083 Uiso calc R 1
C C10 0.24486(14) 0.3469(2) 0.1267(3) 0.0632(6) Uani d . 1
C C11 0.19152(17) 0.3123(3) 0.1708(4) 0.0827(9) Uani d . 1
H H11 0.1385 0.3361 0.1280 0.099 Uiso calc R 1
C C12 0.21650(19) 0.2459(4) 0.2729(4) 0.0950(11) Uani d . 1
H H12 0.1807 0.2246 0.3007 0.114 Uiso calc R 1
C C13 0.2958(2) 0.2080(3) 0.3386(3) 0.0862(9) Uani d . 1
H H13 0.3122 0.1617 0.4095 0.103 Uiso calc R 1
C C14 0.34976(15) 0.2385(3) 0.2997(2) 0.0657(6) Uani d . 1
H H14 0.4022 0.2122 0.3431 0.079 Uiso calc R 1
C C15 0.32525(13) 0.30941(19) 0.1942(2) 0.0522(5) Uani d . 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'
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 0.0060 '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 2_655 . 36.95(19)
O1 Cu1 N1 2_655 . 90.82(10)
O1 Cu1 N1 . . 106.65(10)
O1 Cu1 N1 2_655 2_655 106.65(10)
O1 Cu1 N1 . 2_655 90.82(10)
N1 Cu1 N1 . 2_655 161.74(10)
O1 Cu1 O3 2_655 2_655 143.58(12)
O1 Cu1 O3 . 2_655 108.87(12)
N1 Cu1 O3 . 2_655 89.83(7)
N1 Cu1 O3 2_655 2_655 79.30(7)
O1 Cu1 O3 2_655 . 108.87(12)
O1 Cu1 O3 . . 143.58(12)
N1 Cu1 O3 . . 79.30(7)
N1 Cu1 O3 2_655 . 89.83(7)
O3 Cu1 O3 2_655 . 107.02(13)
C1 O1 O2 2_655 2_655 85.6(5)
O2 O1 O1 2_655 2_655 156.1(4)
O2 O1 C1 2_655 . 127.1(3)
C1 O1 Cu1 2_655 . 145.0(5)
O2 O1 Cu1 2_655 . 124.3(3)
O1 O1 Cu1 2_655 . 71.52(10)
C1 O1 Cu1 . . 106.8(3)
O1 C1 C1 2_655 2_655 102.2(5)
O1 C1 O2 2_655 . 55.5(4)
C1 C1 O2 2_655 . 157.5(4)
O1 C1 O1 2_655 . 69.6(5)
O2 C1 O1 . . 123.6(4)
O1 C1 C2 2_655 . 166.6(5)
C1 C1 C2 2_655 . 73.61(15)
O2 C1 C2 . . 127.5(4)
O1 C1 C2 . . 109.0(3)
C6 O3 Cu1 . . 116.24(14)
C6 O3 H1 . . 109.5
Cu1 O3 H1 . . 132.9
C7 N1 C15 . . 118.85(18)
C7 N1 Cu1 . . 114.11(14)
C15 N1 Cu1 . . 126.73(15)
C3 C2 C3 2_655 . 118.6(3)
C3 C2 C1 2_655 . 104.3(2)
C3 C2 C1 . . 137.1(2)
C3 C2 C1 2_655 2_655 137.1(2)
C3 C2 C1 . 2_655 104.3(2)
C4 C3 C2 . . 120.7(2)
C4 C3 H3 . . 119.6
C2 C3 H3 . . 119.6
C3 C4 C5 . . 120.2(3)
C3 C4 H4 . . 119.9
C5 C4 H4 . . 119.9
C4 C5 C4 2_655 . 119.6(4)
C4 C5 H5 2_655 . 120.2
C4 C5 H5 . . 120.2
O4 C6 O3 . . 128.6(2)
O4 C6 C7 . . 118.4(2)
O3 C6 C7 . . 112.78(19)
N1 C7 C8 . . 123.5(2)
N1 C7 C6 . . 116.81(18)
C8 C7 C6 . . 119.6(2)
C9 C8 C7 . . 118.3(2)
C9 C8 H8 . . 120.9
C7 C8 H8 . . 120.9
C8 C9 C10 . . 120.3(2)
C8 C9 H9 . . 119.9
C10 C9 H9 . . 119.9
C9 C10 C15 . . 118.9(2)
C9 C10 C11 . . 123.0(3)
C15 C10 C11 . . 118.1(3)
C12 C11 C10 . . 120.8(3)
C12 C11 H11 . . 119.6
C10 C11 H11 . . 119.6
C11 C12 C13 . . 120.8(3)
C11 C12 H12 . . 119.6
C13 C12 H12 . . 119.6
C14 C13 C12 . . 120.7(3)
C14 C13 H13 . . 119.7
C12 C13 H13 . . 119.7
C13 C14 C15 . . 119.5(3)
C13 C14 H14 . . 120.3
C15 C14 H14 . . 120.3
N1 C15 C14 . . 119.8(2)
N1 C15 C10 . . 120.2(2)
C14 C15 C10 . . 120.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O1 2_655 1.970(3)
Cu1 O1 . 1.970(3)
Cu1 N1 . 2.0424(16)
Cu1 N1 2_655 2.0424(16)
Cu1 O3 2_655 2.0553(16)
Cu1 O3 . 2.0553(16)
O1 C1 2_655 0.777(4)
O1 O2 2_655 1.018(4)
O1 O1 2_655 1.249(7)
O1 C1 . 1.285(4)
O2 O1 2_655 1.018(4)
O2 C1 . 1.233(5)
C1 O1 2_655 0.777(4)
C1 C1 2_655 0.872(8)
C1 C2 . 1.545(5)
O3 C6 . 1.306(3)
O3 H1 . 0.8200
O4 C6 . 1.187(3)
N1 C7 . 1.318(3)
N1 C15 . 1.378(3)
C2 C3 2_655 1.372(3)
C2 C3 . 1.372(3)
C2 C1 2_655 1.545(5)
C3 C4 . 1.361(4)
C3 H3 . 0.9300
C4 C5 . 1.364(4)
C4 H4 . 0.9300
C5 C4 2_655 1.364(4)
C5 H5 . 0.9300
C6 C7 . 1.508(3)
C7 C8 . 1.407(3)
C8 C9 . 1.358(4)
C8 H8 . 0.9300
C9 C10 . 1.392(4)
C9 H9 . 0.9300
C10 C15 . 1.416(3)
C10 C11 . 1.419(4)
C11 C12 . 1.336(5)
C11 H11 . 0.9300
C12 C13 . 1.400(5)
C12 H12 . 0.9300
C13 C14 . 1.371(4)
C13 H13 . 0.9300
C14 C15 . 1.398(4)
C14 H14 . 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
O3 H1 O4 5_665 0.82 1.76 2.560(3) 165.4
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_4
_geom_torsion
O1 Cu1 O1 C1 2_655 2_655 -15.7(7)
N1 Cu1 O1 C1 . 2_655 52.4(9)
N1 Cu1 O1 C1 2_655 2_655 -132.9(8)
O3 Cu1 O1 C1 2_655 2_655 148.1(8)
O3 Cu1 O1 C1 . 2_655 -42.1(9)
O1 Cu1 O1 O2 2_655 2_655 -159.9(6)
N1 Cu1 O1 O2 . 2_655 -91.8(4)
N1 Cu1 O1 O2 2_655 2_655 82.8(4)
O3 Cu1 O1 O2 2_655 2_655 3.9(4)
O3 Cu1 O1 O2 . 2_655 173.7(3)
N1 Cu1 O1 O1 . 2_655 68.1(3)
N1 Cu1 O1 O1 2_655 2_655 -117.2(3)
O3 Cu1 O1 O1 2_655 2_655 163.8(3)
O3 Cu1 O1 O1 . 2_655 -26.4(4)
O1 Cu1 O1 C1 2_655 . 5.6(2)
N1 Cu1 O1 C1 . . 73.7(3)
N1 Cu1 O1 C1 2_655 . -111.6(2)
O3 Cu1 O1 C1 2_655 . 169.4(2)
O3 Cu1 O1 C1 . . -20.8(3)
O1 O2 C1 C1 2_655 2_655 6.7(16)
O1 O2 C1 O1 2_655 . -15.3(5)
O1 O2 C1 C2 2_655 . 163.8(7)
C1 O1 C1 O1 2_655 2_655 152.6(11)
O2 O1 C1 O1 2_655 2_655 155.8(7)
Cu1 O1 C1 O1 . 2_655 -9.2(4)
O2 O1 C1 C1 2_655 2_655 3.3(8)
O1 O1 C1 C1 2_655 2_655 -152.6(11)
Cu1 O1 C1 C1 . 2_655 -161.7(7)
C1 O1 C1 O2 2_655 . 166.0(10)
O2 O1 C1 O2 2_655 . 169.3(3)
O1 O1 C1 O2 2_655 . 13.4(4)
Cu1 O1 C1 O2 . . 4.2(5)
C1 O1 C1 C2 2_655 . -13.3(5)
O2 O1 C1 C2 2_655 . -10.0(5)
O1 O1 C1 C2 2_655 . -165.9(6)
Cu1 O1 C1 C2 . . -175.0(2)
O1 Cu1 O3 C6 2_655 . 81.1(2)
O1 Cu1 O3 C6 . . 97.5(2)
N1 Cu1 O3 C6 . . -6.11(19)
N1 Cu1 O3 C6 2_655 . -171.4(2)
O3 Cu1 O3 C6 2_655 . -92.6(2)
O1 Cu1 N1 C7 2_655 . -108.25(18)
O1 Cu1 N1 C7 . . -142.16(17)
N1 Cu1 N1 C7 2_655 . 55.17(14)
O3 Cu1 N1 C7 2_655 . 108.16(16)
O3 Cu1 N1 C7 . . 0.80(15)
O1 Cu1 N1 C15 2_655 . 78.21(19)
O1 Cu1 N1 C15 . . 44.3(2)
N1 Cu1 N1 C15 2_655 . -118.37(17)
O3 Cu1 N1 C15 2_655 . -65.38(18)
O3 Cu1 N1 C15 . . -172.74(19)
O1 C1 C2 C3 2_655 2_655 108(2)
C1 C1 C2 C3 2_655 2_655 -179.0(5)
O2 C1 C2 C3 . 2_655 9.9(5)
O1 C1 C2 C3 . 2_655 -170.9(3)
O1 C1 C2 C3 2_655 . -72(2)
C1 C1 C2 C3 2_655 . 1.4(7)
O2 C1 C2 C3 . . -169.7(3)
O1 C1 C2 C3 . . 9.5(4)
O1 C1 C2 C1 2_655 2_655 -73(2)
O2 C1 C2 C1 . 2_655 -171.1(9)
O1 C1 C2 C1 . 2_655 8.2(3)
C3 C2 C3 C4 2_655 . -0.4(2)
C1 C2 C3 C4 . . 179.1(3)
C1 C2 C3 C4 2_655 . 179.9(3)
C2 C3 C4 C5 . . 0.9(4)
C3 C4 C5 C4 . 2_655 -0.4(2)
Cu1 O3 C6 O4 . . -176.0(3)
Cu1 O3 C6 C7 . . 9.5(3)
C15 N1 C7 C8 . . -0.9(3)
Cu1 N1 C7 C8 . . -175.00(18)
C15 N1 C7 C6 . . 177.99(18)
Cu1 N1 C7 C6 . . 3.9(2)
O4 C6 C7 N1 . . 175.9(3)
O3 C6 C7 N1 . . -9.0(3)
O4 C6 C7 C8 . . -5.2(4)
O3 C6 C7 C8 . . 170.0(2)
N1 C7 C8 C9 . . 1.2(4)
C6 C7 C8 C9 . . -177.7(2)
C7 C8 C9 C10 . . 0.1(4)
C8 C9 C10 C15 . . -1.5(4)
C8 C9 C10 C11 . . 178.7(3)
C9 C10 C11 C12 . . 179.6(3)
C15 C10 C11 C12 . . -0.2(4)
C10 C11 C12 C13 . . -0.5(6)
C11 C12 C13 C14 . . 0.1(6)
C12 C13 C14 C15 . . 0.9(5)
C7 N1 C15 C14 . . 179.8(2)
Cu1 N1 C15 C14 . . -6.9(3)
C7 N1 C15 C10 . . -0.6(3)
Cu1 N1 C15 C10 . . 172.68(16)
C13 C14 C15 N1 . . 178.1(2)
C13 C14 C15 C10 . . -1.5(4)
C9 C10 C15 N1 . . 1.8(3)
C11 C10 C15 N1 . . -178.4(2)
C9 C10 C15 C14 . . -178.6(2)
C11 C10 C15 C14 . . 1.2(4)
