#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/55/2225506.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_2225506
loop_
_publ_author_name
'Nie, Jing-Jing'
'Li, Jun-Hua'
'Xu, Duan-Jun'
_publ_section_title
;
 Bis(μ-4-chloro-2-oxidobenzoato)bis[(1,10-phenanthroline)copper(II)]
 dihydrate
;
_journal_coeditor_code           DN2542
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m387
_journal_page_last               m388
_journal_paper_doi               10.1107/S1600536810008354
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu2 (C7 H3 Cl O3)2 (C12 H8 N2)2], 2H2 O'
_chemical_formula_moiety         'C38 H22 Cl2 Cu2 N4 O6, 2(H2 O)'
_chemical_formula_sum            'C38 H26 Cl2 Cu2 N4 O8'
_chemical_formula_weight         864.60
_chemical_name_systematic
;
Bis(μ-4-chloro-2-oxidobenzoato)bis[(1,10-phenanthroline)copper(II)] dihydrate
;
_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                 105.993(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1941(17)
_cell_length_b                   18.851(4)
_cell_length_c                   11.873(3)
_cell_measurement_reflns_used    5352
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.2
_cell_volume                     1763.0(7)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18894
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.09
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.419
_exptl_absorpt_correction_T_max  0.730
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.5996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2162
_reflns_number_total             3163
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2542.cif
_cod_data_source_block           I
_cod_original_cell_volume        1763.0(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225506
_cod_database_fobs_code          2225506
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_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.28977(4) 0.501289(19) 0.46012(3) 0.04370(15) Uani d . 1 . .
Cl Cl 0.68680(17) 0.80306(6) 0.36270(13) 0.1107(5) Uani d . 1 . .
N N1 0.2931(3) 0.50654(13) 0.6296(2) 0.0456(6) Uani d . 1 . .
N N2 0.1240(3) 0.42264(13) 0.4601(2) 0.0480(6) Uani d . 1 . .
O O1 0.2426(3) 0.49404(12) 0.2962(2) 0.0596(6) Uani d . 1 . .
O O2 0.2234(3) 0.52593(16) 0.1153(2) 0.0750(7) Uani d . 1 . .
O O3 0.4451(3) 0.57734(11) 0.47282(18) 0.0507(5) Uani d . 1 . .
C C1 0.2743(4) 0.5384(2) 0.2219(3) 0.0555(9) Uani d . 1 . .
C C2 0.3717(4) 0.60392(18) 0.2646(3) 0.0512(8) Uani d . 1 . .
C C3 0.4487(4) 0.61966(16) 0.3838(3) 0.0472(7) Uani d . 1 . .
C C4 0.5430(4) 0.68293(17) 0.4110(3) 0.0577(9) Uani d . 1 . .
H H4 0.5950 0.6941 0.4889 0.069 Uiso calc R 1 . .
C C5 0.5593(5) 0.72807(19) 0.3250(4) 0.0718(11) Uani d . 1 . .
C C6 0.4837(5) 0.7141(2) 0.2088(4) 0.0851(14) Uani d . 1 . .
H H6 0.4947 0.7455 0.1509 0.102 Uiso calc R 1 . .
C C7 0.3919(5) 0.6528(2) 0.1802(3) 0.0711(11) Uani d . 1 . .
H H7 0.3408 0.6431 0.1015 0.085 Uiso calc R 1 . .
C C8 0.3797(4) 0.55026(19) 0.7127(3) 0.0569(9) Uani d . 1 . .
H H8 0.4424 0.5868 0.6923 0.068 Uiso calc R 1 . .
C C9 0.3792(5) 0.5429(2) 0.8297(3) 0.0728(11) Uani d . 1 . .
H H9 0.4401 0.5745 0.8857 0.087 Uiso calc R 1 . .
C C10 0.2897(5) 0.4896(2) 0.8616(4) 0.0765(13) Uani d . 1 . .
H H10 0.2892 0.4847 0.9394 0.092 Uiso calc R 1 . .
C C11 0.1979(5) 0.4418(2) 0.7767(3) 0.0635(10) Uani d . 1 . .
C C12 0.1001(6) 0.3835(3) 0.7997(4) 0.0854(14) Uani d . 1 . .
H H12 0.0971 0.3746 0.8761 0.102 Uiso calc R 1 . .
C C13 0.0125(6) 0.3412(3) 0.7126(5) 0.0876(14) Uani d . 1 . .
H H13 -0.0510 0.3041 0.7306 0.105 Uiso calc R 1 . .
C C14 0.0135(5) 0.3514(2) 0.5930(4) 0.0675(11) Uani d . 1 . .
C C15 -0.0751(6) 0.3107(2) 0.4968(5) 0.0882(14) Uani d . 1 . .
H H15 -0.1426 0.2731 0.5076 0.106 Uiso calc R 1 . .
C C16 -0.0626(5) 0.3259(2) 0.3884(5) 0.0849(13) Uani d . 1 . .
H H16 -0.1223 0.2990 0.3247 0.102 Uiso calc R 1 . .
C C17 0.0394(5) 0.38181(19) 0.3716(3) 0.0639(10) Uani d . 1 . .
H H17 0.0486 0.3909 0.2966 0.077 Uiso calc R 1 . .
C C18 0.1106(4) 0.40810(17) 0.5688(3) 0.0505(8) Uani d . 1 . .
C C19 0.2019(4) 0.45334(17) 0.6605(3) 0.0499(8) Uani d . 1 . .
O O1W 0.0002(4) 0.59767(16) -0.0734(2) 0.0934(9) Uani d . 1 . .
H H1A 0.0653 0.5735 -0.0124 0.140 Uiso d R 1 . .
H H1B -0.0941 0.5733 -0.0960 0.140 Uiso d R 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'
Cl Cl 0.1484 0.1585 '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 Cu O3 . . 94.54(9) .
O1 Cu N1 . . 169.27(10) .
O3 Cu N1 . . 93.42(10) .
O1 Cu N2 . . 90.01(10) .
O3 Cu N2 . . 175.25(9) .
N1 Cu N2 . . 81.90(11) .
O1 Cu O3 . 3_666 101.17(9) .
O3 Cu O3 . 3_666 85.40(9) .
N1 Cu O3 . 3_666 86.62(8) .
N2 Cu O3 . 3_666 95.07(9) .
C8 N1 C19 . . 118.5(3) ?
C8 N1 Cu . . 129.1(2) ?
C19 N1 Cu . . 112.2(2) ?
C17 N2 C18 . . 118.3(3) ?
C17 N2 Cu . . 129.1(3) ?
C18 N2 Cu . . 112.4(2) ?
C1 O1 Cu . . 129.5(2) ?
C3 O3 Cu . . 123.5(2) ?
O2 C1 O1 . . 119.9(3) ?
O2 C1 C2 . . 120.3(3) ?
O1 C1 C2 . . 119.8(3) ?
C7 C2 C3 . . 118.0(3) ?
C7 C2 C1 . . 117.4(3) ?
C3 C2 C1 . . 124.6(3) ?
O3 C3 C4 . . 117.2(3) ?
O3 C3 C2 . . 124.6(3) ?
C4 C3 C2 . . 118.2(3) ?
C5 C4 C3 . . 121.2(4) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C6 C5 C4 . . 121.5(4) ?
C6 C5 Cl . . 119.1(3) ?
C4 C5 Cl . . 119.4(3) ?
C5 C6 C7 . . 118.5(3) ?
C5 C6 H6 . . 120.8 ?
C7 C6 H6 . . 120.8 ?
C6 C7 C2 . . 122.7(4) ?
C6 C7 H7 . . 118.6 ?
C2 C7 H7 . . 118.6 ?
N1 C8 C9 . . 121.9(4) ?
N1 C8 H8 . . 119.1 ?
C9 C8 H8 . . 119.1 ?
C10 C9 C8 . . 120.1(4) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C10 C11 . . 119.8(4) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C10 C11 C19 . . 116.9(4) ?
C10 C11 C12 . . 125.0(4) ?
C19 C11 C12 . . 118.1(4) ?
C13 C12 C11 . . 121.2(4) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C14 . . 122.2(4) ?
C12 C13 H13 . . 118.9 ?
C14 C13 H13 . . 118.9 ?
C15 C14 C18 . . 116.3(4) ?
C15 C14 C13 . . 126.2(4) ?
C18 C14 C13 . . 117.5(4) ?
C16 C15 C14 . . 120.2(4) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 120.3(4) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
N2 C17 C16 . . 121.8(4) ?
N2 C17 H17 . . 119.1 ?
C16 C17 H17 . . 119.1 ?
N2 C18 C14 . . 123.2(3) ?
N2 C18 C19 . . 116.4(3) ?
C14 C18 C19 . . 120.4(3) ?
N1 C19 C11 . . 122.8(3) ?
N1 C19 C18 . . 116.6(3) ?
C11 C19 C18 . . 120.6(3) ?
H1A O1W H1B . . 105.1 ?
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 O1 . 1.882(2) ?
Cu O3 . 1.895(2) ?
Cu O3 3_666 2.569(2) ?
Cu N1 . 2.007(3) ?
Cu N2 . 2.011(3) ?
Cl C5 . 1.741(4) ?
N1 C8 . 1.331(4) ?
N1 C19 . 1.360(4) ?
N2 C17 . 1.332(4) ?
N2 C18 . 1.353(4) ?
O1 C1 . 1.292(4) ?
O2 C1 . 1.241(4) ?
O3 C3 . 1.331(4) ?
C1 C2 . 1.482(5) ?
C2 C7 . 1.404(4) ?
C2 C3 . 1.413(4) ?
C3 C4 . 1.409(5) ?
C4 C5 . 1.363(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(6) ?
C6 C7 . 1.370(6) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.397(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.358(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.405(6) ?
C10 H10 . 0.9300 ?
C11 C19 . 1.406(4) ?
C11 C12 . 1.430(6) ?
C12 C13 . 1.346(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.435(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.401(6) ?
C14 C18 . 1.409(5) ?
C15 C16 . 1.350(6) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.393(5) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 C19 . 1.423(5) ?
O1W H1A . 0.8969 ?
O1W H1B . 0.8747 ?
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
_geom_hbond_publ_flag
O1W H1A O2 . 0.90 1.92 2.817(4) 175 y
O1W H1B O2 3_565 0.88 2.13 2.921(4) 150 y
C10 H10 O2 1_556 0.93 2.42 3.277(5) 153 y
C17 H17 O1W 3_565 0.93 2.58 3.487(4) 166 y
