#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226030.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_2226030
loop_
_publ_author_name
'Huang, Wen-Xiang'
'Liu, Bin-Bin'
'Lin, Jian-Li'
_publ_section_title
;
 (Benzoato-κO)bis(1,10-phenanthroline-κ²N,N')copper(II)
 chloride benzoic acid disolvate
;
_journal_coeditor_code           ZQ2032
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m488
_journal_page_last               m489
_journal_paper_doi               10.1107/S1600536810011487
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C7 H5 O2) (C12 H8 N2)2] Cl, 2C7 H6 O2'
_chemical_formula_moiety         'C31 H21 Cu N4 O2 +, Cl -, 2(C7 H6 O2)'
_chemical_formula_sum            'C45 H33 Cl Cu N4 O6'
_chemical_formula_weight         824.74
_chemical_name_systematic
;
(Benzoato-κO)bis(1,10-phenanthroline-κ²N,N')copper(II)
chloride benzoic acid disolvate
;
_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                 113.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.724(3)
_cell_length_b                   19.288(4)
_cell_length_c                   13.295(3)
_cell_measurement_reflns_used    15193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.24
_cell_volume                     3922.1(17)
_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)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15193
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1700
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.454
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0393P)²+3.5087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                2623
_reflns_number_total             3449
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zq2032.cif
_cod_data_source_block           I
_cod_original_cell_volume        3922.1(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226030
_cod_database_fobs_code          2226030
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_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.5000 0.26282(3) 0.2500 0.05651(17) Uani d S 1 . .
N N1 0.40747(13) 0.19982(11) 0.12871(18) 0.0554(5) Uani d . 1 . .
N N2 0.40438(13) 0.26263(12) 0.30525(18) 0.0565(5) Uani d . 1 . .
O O1 0.4521(4) 0.3849(3) 0.1410(5) 0.090(2) Uani d P 0.50 . .
O O2 0.5351(3) 0.3568(3) 0.3129(5) 0.0600(12) Uani d P 0.50 . .
C C1 0.5000 0.4012(3) 0.2500 0.0678(11) Uani d S 1 . .
C C2 0.5084(4) 0.47718(18) 0.2698(3) 0.0556(17) Uani d PG 0.50 . .
C C3 0.4829(4) 0.5284(3) 0.1894(2) 0.0788(19) Uani d PG 0.50 . .
H H3A 0.4598 0.5159 0.1131 0.095 Uiso d PR 0.50 . .
C C4 0.4907(5) 0.5979(2) 0.2196(3) 0.075(3) Uani d PG 0.50 . .
H H4A 0.4731 0.6333 0.1641 0.090 Uiso d PR 0.50 . .
C C5 0.5240(5) 0.61615(16) 0.3302(4) 0.084(3) Uani d PG 0.50 . .
H H5A 0.5295 0.6641 0.3511 0.100 Uiso d PR 0.50 . .
C C6 0.5495(3) 0.5649(2) 0.4106(3) 0.0794(18) Uani d PG 0.50 . .
H H6A 0.5726 0.5775 0.4869 0.095 Uiso d PR 0.50 . .
C C7 0.5417(3) 0.49540(19) 0.3803(3) 0.0639(15) Uani d PG 0.50 . .
H H7A 0.5593 0.4600 0.4358 0.077 Uiso d PR 0.50 . .
C C8 0.4095(2) 0.16743(16) 0.0414(2) 0.0694(8) Uani d . 1 . .
H H8A 0.4614 0.1678 0.0313 0.083 Uiso calc R 1 . .
C C9 0.3373(2) 0.13300(16) -0.0355(3) 0.0791(9) Uani d . 1 . .
H H9A 0.3417 0.1106 -0.0950 0.095 Uiso calc R 1 . .
C C10 0.2608(2) 0.13242(17) -0.0231(3) 0.0794(9) Uani d . 1 . .
H H10A 0.2123 0.1097 -0.0742 0.095 Uiso calc R 1 . .
C C11 0.25483(17) 0.16598(14) 0.0667(2) 0.0620(7) Uani d . 1 . .
C C12 0.17667(18) 0.16982(17) 0.0868(3) 0.0790(9) Uani d . 1 . .
H H12A 0.1260 0.1485 0.0379 0.095 Uiso calc R 1 . .
C C13 0.17515(18) 0.20324(17) 0.1738(3) 0.0773(9) Uani d . 1 . .
H H13A 0.1231 0.2055 0.1835 0.093 Uiso calc R 1 . .
C C14 0.25144(16) 0.23560(14) 0.2524(2) 0.0596(7) Uani d . 1 . .
C C15 0.25428(19) 0.27038(17) 0.3459(3) 0.0726(8) Uani d . 1 . .
H H15A 0.2041 0.2741 0.3596 0.087 Uiso calc R 1 . .
C C16 0.3303(2) 0.29866(18) 0.4164(3) 0.0773(9) Uani d . 1 . .
H H16A 0.3330 0.3211 0.4796 0.093 Uiso calc R 1 . .
C C17 0.40467(19) 0.29405(17) 0.3938(3) 0.0728(8) Uani d . 1 . .
H H17A 0.4565 0.3138 0.4430 0.087 Uiso calc R 1 . .
C C18 0.32904(15) 0.23281(13) 0.2352(2) 0.0502(6) Uani d . 1 . .
C C19 0.33051(15) 0.19836(13) 0.1411(2) 0.0509(6) Uani d . 1 . .
C C20 0.6442(2) 0.89663(16) 0.5209(3) 0.0723(8) Uani d . 1 . .
C C21 0.6652(2) 0.94046(15) 0.6202(3) 0.0673(8) Uani d . 1 . .
C C22 0.7514(2) 0.9571(2) 0.6830(3) 0.0868(10) Uani d . 1 . .
H H22A 0.7949 0.9405 0.6626 0.104 Uiso calc R 1 . .
C C23 0.7738(3) 0.9976(2) 0.7744(3) 0.1056(12) Uani d . 1 . .
H H23A 0.8322 1.0083 0.8157 0.127 Uiso calc R 1 . .
C C24 0.7114(3) 1.0223(2) 0.8054(4) 0.1033(12) Uani d . 1 . .
H H24A 0.7268 1.0498 0.8680 0.124 Uiso calc R 1 . .
C C25 0.6259(3) 1.0067(2) 0.7445(4) 0.1094(14) Uani d . 1 . .
H H25A 0.5833 1.0236 0.7662 0.131 Uiso calc R 1 . .
C C26 0.6014(2) 0.96621(18) 0.6513(3) 0.0901(11) Uani d . 1 . .
H H26A 0.5427 0.9564 0.6100 0.108 Uiso calc R 1 . .
Cl Cl 0.5000 0.80270(7) 0.2500 0.0916(4) Uani d S 1 . .
O O4 0.69924(15) 0.87024(14) 0.4972(2) 0.1004(8) Uani d . 1 . .
O O3 0.55968(17) 0.88975(14) 0.4593(2) 0.0977(8) Uani d . 1 . .
H H31 0.544(3) 0.867(2) 0.400(3) 0.117 Uiso 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'
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'
Cl Cl 0.1484 0.1585 '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
O2 Cu O2 . 2_655 47.8(3) ?
O2 Cu N2 . 2_655 90.69(16) ?
O2 Cu N2 2_655 2_655 89.49(16) ?
O2 Cu N2 . . 89.49(16) ?
O2 Cu N2 2_655 . 90.69(16) ?
N2 Cu N2 2_655 . 179.80(13) ?
O2 Cu N1 . . 148.10(18) ?
O2 Cu N1 2_655 . 101.76(18) ?
N2 Cu N1 2_655 . 99.53(8) ?
N2 Cu N1 . . 80.35(8) ?
O2 Cu N1 . 2_655 101.76(18) ?
O2 Cu N1 2_655 2_655 148.10(18) ?
N2 Cu N1 2_655 2_655 80.35(8) ?
N2 Cu N1 . 2_655 99.53(8) ?
N1 Cu N1 . 2_655 109.69(12) ?
C8 N1 C19 . . 117.0(2) ?
C8 N1 Cu . . 131.86(18) ?
C19 N1 Cu . . 110.87(16) ?
C17 N2 C18 . . 118.3(2) ?
C17 N2 Cu . . 127.38(19) ?
C18 N2 Cu . . 113.88(16) ?
C1 O2 Cu . . 112.8(4) ?
O2 C1 O1 . . 119.6(6) ?
O2 C1 C2 . . 127.5(4) ?
O1 C1 C2 . . 112.6(4) ?
C3 C2 C7 . . 120.0 ?
C3 C2 C1 . . 126.0(3) ?
C7 C2 C1 . . 113.9(3) ?
C4 C3 C2 . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C2 C3 H3A . . 120.0 ?
C3 C4 C5 . . 120.0 ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C4 C5 C6 . . 120.0 ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C7 C6 C5 . . 120.0 ?
C7 C6 H6A . . 120.0 ?
C5 C6 H6A . . 120.0 ?
C6 C7 C2 . . 120.0 ?
C6 C7 H7A . . 120.0 ?
C2 C7 H7A . . 120.0 ?
N1 C8 C9 . . 122.9(3) ?
N1 C8 H8A . . 118.5 ?
C9 C8 H8A . . 118.5 ?
C10 C9 C8 . . 119.6(3) ?
C10 C9 H9A . . 120.2 ?
C8 C9 H9A . . 120.2 ?
C9 C10 C11 . . 119.9(3) ?
C9 C10 H10A . . 120.1 ?
C11 C10 H10A . . 120.1 ?
C10 C11 C19 . . 117.1(3) ?
C10 C11 C12 . . 124.5(3) ?
C19 C11 C12 . . 118.4(3) ?
C13 C12 C11 . . 121.6(3) ?
C13 C12 H12A . . 119.2 ?
C11 C12 H12A . . 119.2 ?
C12 C13 C14 . . 121.5(3) ?
C12 C13 H13A . . 119.3 ?
C14 C13 H13A . . 119.3 ?
C15 C14 C18 . . 117.5(3) ?
C15 C14 C13 . . 124.1(3) ?
C18 C14 C13 . . 118.4(3) ?
C16 C15 C14 . . 119.7(2) ?
C16 C15 H15A . . 120.2 ?
C14 C15 H15A . . 120.2 ?
C15 C16 C17 . . 119.7(3) ?
C15 C16 H16A . . 120.2 ?
C17 C16 H16A . . 120.2 ?
N2 C17 C16 . . 122.6(3) ?
N2 C17 H17A . . 118.7 ?
C16 C17 H17A . . 118.7 ?
N2 C18 C14 . . 122.3(2) ?
N2 C18 C19 . . 117.4(2) ?
C14 C18 C19 . . 120.3(2) ?
N1 C19 C11 . . 123.5(2) ?
N1 C19 C18 . . 116.7(2) ?
C11 C19 C18 . . 119.8(2) ?
O4 C20 O3 . . 122.4(3) ?
O4 C20 C21 . . 122.9(3) ?
O3 C20 C21 . . 114.6(3) ?
C22 C21 C26 . . 118.6(3) ?
C22 C21 C20 . . 119.0(3) ?
C26 C21 C20 . . 122.5(3) ?
C23 C22 C21 . . 121.1(3) ?
C23 C22 H22A . . 119.5 ?
C21 C22 H22A . . 119.5 ?
C24 C23 C22 . . 120.3(4) ?
C24 C23 H23A . . 119.8 ?
C22 C23 H23A . . 119.8 ?
C23 C24 C25 . . 119.6(4) ?
C23 C24 H24A . . 120.2 ?
C25 C24 H24A . . 120.2 ?
C24 C25 C26 . . 121.3(3) ?
C24 C25 H25A . . 119.4 ?
C26 C25 H25A . . 119.4 ?
C25 C26 C21 . . 119.2(4) ?
C25 C26 H26A . . 120.4 ?
C21 C26 H26A . . 120.4 ?
C20 O3 H31 . . 119(3) ?
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 O2 . 1.984(5) ?
Cu O2 2_655 1.984(5) ?
Cu N2 2_655 2.012(2) ?
Cu N2 . 2.012(2) ?
Cu N1 . 2.110(2) ?
Cu N1 2_655 2.110(2) ?
N1 C8 . 1.330(3) ?
N1 C19 . 1.362(3) ?
N2 C17 . 1.322(3) ?
N2 C18 . 1.355(3) ?
O1 C1 . 1.378(6) ?
O2 C1 . 1.174(6) ?
C1 C2 . 1.486(6) ?
C2 C3 . 1.3900 ?
C2 C7 . 1.3900 ?
C3 C4 . 1.3900 ?
C3 H3A . 0.9600 ?
C4 C5 . 1.3900 ?
C4 H4A . 0.9600 ?
C5 C6 . 1.3900 ?
C5 H5A . 0.9601 ?
C6 C7 . 1.3900 ?
C6 H6A . 0.9599 ?
C7 H7A . 0.9601 ?
C8 C9 . 1.395(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.356(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.395(4) ?
C10 H10A . 0.9300 ?
C11 C19 . 1.399(4) ?
C11 C12 . 1.438(4) ?
C12 C13 . 1.334(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.425(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.396(4) ?
C14 C18 . 1.407(3) ?
C15 C16 . 1.352(4) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.395(4) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9300 ?
C18 C19 . 1.425(3) ?
C20 O4 . 1.200(3) ?
C20 O3 . 1.323(4) ?
C20 C21 . 1.485(4) ?
C21 C22 . 1.380(5) ?
C21 C26 . 1.384(4) ?
C22 C23 . 1.363(5) ?
C22 H22A . 0.9300 ?
C23 C24 . 1.355(5) ?
C23 H23A . 0.9300 ?
C24 C25 . 1.361(5) ?
C24 H24A . 0.9300 ?
C25 C26 . 1.379(5) ?
C25 H25A . 0.9300 ?
C26 H26A . 0.9300 ?
Cl Cl 2_655 0.000(3) ?
O3 H31 . 0.85(4) ?
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
C5 H5A Cl . 0.96 2.94 3.728(4) 139.9
O3 H31 Cl . 0.85(4) 2.20(4) 3.051(3) 177(4)
O3 H31 Cl 2_655 0.85(4) 2.20(4) 3.051(3) 177(4)
C24 H24A O4 6_576 0.93 2.49 3.355(5) 155.3
C8 H8A O3 6_565 0.93 2.47 3.307(4) 149.0
C10 H10A O1 7 0.93 2.53 3.275(7) 137.7
C12 H12A O1 7 0.93 2.30 3.106(7) 145.5
