#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/30/2203088.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_2203088
loop_
_publ_author_name
'Hong-Ping Xiao'
'Mao-Lin Hu'
'Xin-Hua Li'
_publ_section_title
;
 Bis[bis(1,10-phenanthroline)chlorocopper(II)]
 benzene-1,2,4,5-tetracarboxylate(2--) dihydrate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m71
_journal_page_last               m72
_journal_paper_doi               10.1107/S1600536803028101
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu Cl (C12 H8 N2)2]2 (C10 H4 O8), 2H2 O'
_chemical_formula_moiety         'C48 H32 Cl2 Cu2 N8 1+, C10 H4 O8 2-, 2H2 O'
_chemical_formula_sum            'C58 H40 Cl2 Cu2 N8 O10'
_chemical_formula_weight         1206.96
_chemical_name_systematic
;
Bis[bis(1,10-phenanthroline)chlorocopper(II)]
benzene-1,2,4,5-tetracarboxylate(2-) dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.0410(10)
_cell_angle_beta                 95.2080(10)
_cell_angle_gamma                110.6850(10)
_cell_formula_units_Z            1
_cell_length_a                   10.1324(7)
_cell_length_b                   11.3356(8)
_cell_length_c                   12.2000(9)
_cell_measurement_reflns_used    426
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.42
_cell_measurement_theta_min      2.32
_cell_volume                     1247.48(15)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART 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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6633
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.296
_refine_ls_extinction_coef       0.0094(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.005
_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+0.4259P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                3992
_reflns_number_total             4388
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng6004.cif
_cod_data_source_block           I
_cod_database_code               2203088
_cod_database_fobs_code          2203088
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Cu1 0.24732(2) 0.91663(2) 0.20963(2) 0.03775(12) Uani d . 1 Cu
Cl1 0.34267(6) 0.82258(6) 0.06828(5) 0.04827(16) Uani d . 1 Cl
O1 0.88315(19) 0.6249(2) 0.50569(19) 0.0704(6) Uani d . 1 O
O2 0.7969(2) 0.6520(3) 0.3499(2) 0.1046(10) Uani d . 1 O
O3 0.5737(2) 0.5563(3) 0.21317(18) 0.0872(8) Uani d D 1 O
O4 0.3492(2) 0.4471(2) 0.20433(16) 0.0804(7) Uani d . 1 O
O5 0.0295(3) 0.4912(3) 0.3320(2) 0.0831(7) Uani d D 1 O
N1 0.05525(19) 0.76799(18) 0.15257(15) 0.0400(4) Uani d . 1 N
N2 0.11811(18) 1.02440(18) 0.17589(14) 0.0375(4) Uani d . 1 N
N3 0.23036(18) 0.94894(17) 0.38435(15) 0.0378(4) Uani d . 1 N
N4 0.43377(19) 1.07138(18) 0.28032(15) 0.0388(4) Uani d . 1 N
C1 0.0281(3) 0.6415(2) 0.1394(2) 0.0496(6) Uani d . 1 C
H1 0.1023 0.6176 0.1630 0.060 Uiso calc R 1 H
C2 -0.1086(3) 0.5432(3) 0.0912(2) 0.0571(7) Uani d . 1 C
H2 -0.1243 0.4552 0.0825 0.068 Uiso calc R 1 H
C3 -0.2185(3) 0.5764(3) 0.0571(2) 0.0557(7) Uani d . 1 C
H3 -0.3090 0.5110 0.0229 0.067 Uiso calc R 1 H
C4 -0.1952(2) 0.7099(3) 0.07352(17) 0.0471(6) Uani d . 1 C
C5 -0.3044(2) 0.7565(3) 0.0456(2) 0.0571(7) Uani d . 1 C
H5 -0.3984 0.6961 0.0153 0.068 Uiso calc R 1 H
C6 -0.2738(3) 0.8855(3) 0.0622(2) 0.0569(7) Uani d . 1 C
H6 -0.3475 0.9126 0.0443 0.068 Uiso calc R 1 H
C7 -0.1307(2) 0.9824(3) 0.10656(18) 0.0453(5) Uani d . 1 C
C8 -0.0908(3) 1.1183(3) 0.1232(2) 0.0534(6) Uani d . 1 C
H8 -0.1598 1.1508 0.1052 0.064 Uiso calc R 1 H
C9 0.0491(3) 1.2030(3) 0.1658(2) 0.0527(6) Uani d . 1 C
H9 0.0759 1.2932 0.1781 0.063 Uiso calc R 1 H
C10 0.1514(3) 1.1520(2) 0.19067(19) 0.0437(5) Uani d . 1 C
H10 0.2468 1.2099 0.2187 0.052 Uiso calc R 1 H
C11 -0.0212(2) 0.9405(2) 0.13558(16) 0.0370(5) Uani d . 1 C
C12 -0.0544(2) 0.8027(2) 0.12087(16) 0.0381(5) Uani d . 1 C
C13 0.1254(2) 0.8900(2) 0.4338(2) 0.0469(5) Uani d . 1 C
H13 0.0436 0.8204 0.3877 0.056 Uiso calc R 1 H
C14 0.1332(3) 0.9284(3) 0.5524(2) 0.0550(6) Uani d . 1 C
H14 0.0563 0.8867 0.5842 0.066 Uiso calc R 1 H
C15 0.2544(3) 1.0277(3) 0.6216(2) 0.0547(6) Uani d . 1 C
H15 0.2610 1.0529 0.7010 0.066 Uiso calc R 1 H
C16 0.3686(3) 1.0915(2) 0.57306(19) 0.0417(5) Uani d . 1 C
C17 0.5020(3) 1.1935(2) 0.6385(2) 0.0484(6) Uani d . 1 C
H17 0.5166 1.2196 0.7185 0.058 Uiso calc R 1 H
C18 0.6071(3) 1.2524(2) 0.5856(2) 0.0478(6) Uani d . 1 C
H18 0.6931 1.3179 0.6299 0.057 Uiso calc R 1 H
C19 0.5883(2) 1.2159(2) 0.4626(2) 0.0411(5) Uani d . 1 C
C20 0.6901(2) 1.2768(2) 0.4022(2) 0.0499(6) Uani d . 1 C
H20 0.7772 1.3442 0.4421 0.060 Uiso calc R 1 H
C21 0.6612(3) 1.2369(2) 0.2849(2) 0.0534(6) Uani d . 1 C
H21 0.7268 1.2791 0.2444 0.064 Uiso calc R 1 H
C22 0.5324(3) 1.1324(2) 0.2260(2) 0.0484(6) Uani d . 1 C
H22 0.5150 1.1044 0.1459 0.058 Uiso calc R 1 H
C23 0.4597(2) 1.1137(2) 0.39706(18) 0.0355(4) Uani d . 1 C
C24 0.3500(2) 1.0493(2) 0.45273(17) 0.0351(4) Uani d . 1 C
C25 0.4699(3) 0.4986(2) 0.2584(2) 0.0481(6) Uani d D 1 C
C26 0.3739(2) 0.4507(2) 0.42571(18) 0.0371(5) Uani d . 1 C
H26 0.2867 0.4166 0.3742 0.044 Uiso calc R 1 H
C27 0.4987(2) 0.5034(2) 0.38457(17) 0.0361(4) Uani d . 1 C
C28 0.6304(2) 0.5549(2) 0.46221(18) 0.0363(4) Uani d . 1 C
C29 0.7826(3) 0.6148(2) 0.4387(2) 0.0482(6) Uani d . 1 C
H31 0.054(4) 0.446(3) 0.371(3) 0.113(15) Uiso d D 1 H
H30 -0.016(3) 0.538(3) 0.361(2) 0.080(11) Uiso d D 1 H
H32 0.6417(18) 0.600(4) 0.2713(15) 0.139(19) Uiso d D 1 H
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
_geom_angle_publ_flag
N1 Cu1 N2 . 80.38(7) yes
N1 Cu1 N3 . 94.34(7) yes
N1 Cu1 N4 . 174.67(7) yes
N1 Cu1 Cl1 . 92.15(5) yes
N2 Cu1 N4 . 97.93(7) yes
N2 Cu1 N3 . 93.90(7) yes
N2 Cu1 Cl1 . 121.04(5) yes
N3 Cu1 N4 . 80.70(7) yes
N3 Cu1 Cl1 . 145.05(5) yes
N4 Cu1 Cl1 . 93.04(5) yes
C25 O3 H32 . 102.6(11) no
H31 O5 H30 . 118.9(19) no
C1 N1 C12 . 118.74(19) no
C1 N1 Cu1 . 126.14(17) no
C12 N1 Cu1 . 115.07(14) no
C10 N2 C11 . 118.37(19) no
C10 N2 Cu1 . 131.65(15) no
C11 N2 Cu1 . 109.95(14) no
C13 N3 C24 . 118.23(19) no
C13 N3 Cu1 . 130.97(15) no
C24 N3 Cu1 . 110.79(13) no
C22 N4 C23 . 118.40(19) no
C22 N4 Cu1 . 127.43(16) no
C23 N4 Cu1 . 114.15(14) no
N1 C1 C2 . 122.0(2) no
N1 C1 H1 . 119.0 no
C2 C1 H1 . 119.0 no
C3 C2 C1 . 119.8(3) no
C3 C2 H2 . 120.1 no
C1 C2 H2 . 120.1 no
C2 C3 C4 . 119.9(2) no
C2 C3 H3 . 120.1 no
C4 C3 H3 . 120.1 no
C12 C4 C3 . 116.8(2) no
C12 C4 C5 . 118.5(2) no
C3 C4 C5 . 124.6(2) no
C6 C5 C4 . 121.4(2) no
C6 C5 H5 . 119.3 no
C4 C5 H5 . 119.3 no
C5 C6 C7 . 121.6(2) no
C5 C6 H6 . 119.2 no
C7 C6 H6 . 119.2 no
C11 C7 C8 . 116.8(2) no
C11 C7 C6 . 118.6(2) no
C8 C7 C6 . 124.6(2) no
C9 C8 C7 . 120.1(2) no
C9 C8 H8 . 119.9 no
C7 C8 H8 . 119.9 no
C8 C9 C10 . 119.0(2) no
C8 C9 H9 . 120.5 no
C10 C9 H9 . 120.5 no
N2 C10 C9 . 122.7(2) no
N2 C10 H10 . 118.7 no
C9 C10 H10 . 118.7 no
N2 C11 C7 . 122.9(2) no
N2 C11 C12 . 117.23(18) no
C7 C11 C12 . 119.8(2) no
N1 C12 C4 . 122.7(2) no
N1 C12 C11 . 117.33(18) no
C4 C12 C11 . 120.0(2) no
N3 C13 C14 . 122.4(2) no
N3 C13 H13 . 118.8 no
C14 C13 H13 . 118.8 no
C15 C14 C13 . 119.5(2) no
C15 C14 H14 . 120.2 no
C13 C14 H14 . 120.2 no
C14 C15 C16 . 119.9(2) no
C14 C15 H15 . 120.0 no
C16 C15 H15 . 120.0 no
C15 C16 C24 . 116.8(2) no
C15 C16 C17 . 124.2(2) no
C24 C16 C17 . 119.1(2) no
C18 C17 C16 . 121.0(2) no
C18 C17 H17 . 119.5 no
C16 C17 H17 . 119.5 no
C17 C18 C19 . 121.2(2) no
C17 C18 H18 . 119.4 no
C19 C18 H18 . 119.4 no
C20 C19 C23 . 117.2(2) no
C20 C19 C18 . 124.1(2) no
C23 C19 C18 . 118.7(2) no
C21 C20 C19 . 119.8(2) no
C21 C20 H20 . 120.1 no
C19 C20 H20 . 120.1 no
C20 C21 C22 . 119.6(2) no
C20 C21 H21 . 120.2 no
C22 C21 H21 . 120.2 no
N4 C22 C21 . 122.3(2) no
N4 C22 H22 . 118.9 no
C21 C22 H22 . 118.9 no
N4 C23 C19 . 122.64(19) no
N4 C23 C24 . 117.11(18) no
C19 C23 C24 . 120.25(19) no
N3 C24 C16 . 123.1(2) no
N3 C24 C23 . 117.13(18) no
C16 C24 C23 . 119.8(2) no
O4 C25 O3 . 120.5(2) no
O4 C25 C27 . 119.7(2) no
O3 C25 C27 . 119.6(2) no
C28 C26 C27 2_666 124.9(2) no
C28 C26 H26 2_666 117.5 no
C27 C26 H26 . 117.5 no
C26 C27 C28 . 117.60(19) no
C26 C27 C25 . 113.23(19) no
C28 C27 C25 . 129.2(2) no
C26 C28 C27 2_666 117.46(19) no
C26 C28 C29 2_666 114.4(2) no
C27 C28 C29 . 128.15(19) no
O1 C29 O2 . 122.5(2) no
O1 C29 C28 . 119.0(2) no
O2 C29 C28 . 118.5(2) no
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
Cu1 N1 . 1.9949(18) yes
Cu1 N2 . 2.1569(18) yes
Cu1 N3 . 2.1071(17) yes
Cu1 N4 . 2.0047(18) yes
Cu1 Cl1 . 2.2763(6) yes
O1 C29 . 1.200(3) no
O2 C29 . 1.256(3) no
O3 C25 . 1.278(3) no
O3 H32 . 0.851(10) no
O4 C25 . 1.197(3) no
O5 H31 . 0.855(10) no
O5 H30 . 0.849(10) no
N1 C1 . 1.326(3) no
N1 C12 . 1.358(3) no
N2 C10 . 1.325(3) no
N2 C11 . 1.355(3) no
N3 C13 . 1.323(3) no
N3 C24 . 1.357(3) no
N4 C22 . 1.331(3) no
N4 C23 . 1.356(3) no
C1 C2 . 1.397(4) no
C1 H1 . 0.9300 no
C2 C3 . 1.357(4) no
C2 H2 . 0.9300 no
C3 C4 . 1.407(4) no
C3 H3 . 0.9300 no
C4 C12 . 1.404(3) no
C4 C5 . 1.431(4) no
C5 C6 . 1.342(4) no
C5 H5 . 0.9300 no
C6 C7 . 1.430(4) no
C6 H6 . 0.9300 no
C7 C11 . 1.402(3) no
C7 C8 . 1.405(4) no
C8 C9 . 1.365(4) no
C8 H8 . 0.9300 no
C9 C10 . 1.397(3) no
C9 H9 . 0.9300 no
C10 H10 . 0.9300 no
C11 C12 . 1.438(3) no
C13 C14 . 1.392(3) no
C13 H13 . 0.9300 no
C14 C15 . 1.365(4) no
C14 H14 . 0.9300 no
C15 C16 . 1.398(3) no
C15 H15 . 0.9300 no
C16 C24 . 1.402(3) no
C16 C17 . 1.433(3) no
C17 C18 . 1.351(4) no
C17 H17 . 0.9300 no
C18 C19 . 1.432(3) no
C18 H18 . 0.9300 no
C19 C20 . 1.402(3) no
C19 C23 . 1.405(3) no
C20 C21 . 1.361(4) no
C20 H20 . 0.9300 no
C21 C22 . 1.395(3) no
C21 H21 . 0.9300 no
C22 H22 . 0.9300 no
C23 C24 . 1.426(3) no
C25 C27 . 1.525(3) no
C26 C28 2_666 1.388(3) no
C26 C27 . 1.391(3) no
C26 H26 . 0.9300 no
C27 C28 . 1.404(3) no
C28 C26 2_666 1.388(3) no
C28 C29 . 1.535(3) no
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
O5 H31 O1 2_666 0.855(10) 2.025(14) 2.864(3) 167(3) yes
O5 H30 O1 1_455 0.849(10) 2.313(17) 3.096(3) 154(3) yes
O3 H32 O2 . 0.851(10) 1.593(18) 2.404(3) 158(4) yes
