#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/84/2018461.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_2018461
loop_
_publ_author_name
'Moncol, Ján'
'Jomová, Klaudia'
'Porubská, Mária'
_publ_section_title
;
 Two centrosymmetric dinuclear phenanthroline--copper(II) complexes with
 3,5-dichloro-2-hydroxybenzoic acid and 5-chloro-2-hydroxybenzoic acid
;
_journal_coeditor_code           SF3164
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m85
_journal_page_last               m89
_journal_paper_doi               10.1107/S0108270112004532
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac
'[Cu2 (C7 H2 Cl2 O3)2 (C12 H8 N2)2 (C7 H4 Cl2 O3)2]'
_chemical_formula_moiety         'C52 H28 Cl8 Cu2 N4 O12'
_chemical_formula_sum            'C52 H28 Cl8 Cu2 N4 O12'
_chemical_formula_weight         1311.48
_chemical_name_systematic
;
bis(μ-3,5-dichloro-2-oxidobenzoato)-
κ³O¹,O²:O²;
κ³O²:O¹,O²-
bis[(3,5-dichloro-2-hydroxybenzoic acid-κO¹)(1,10-
phenanthroline-κ²N,N')copper(II)]
;
_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                102.423(2)
_cell_angle_beta                 99.045(2)
_cell_angle_gamma                106.753(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2295(2)
_cell_length_b                   11.6047(3)
_cell_length_c                   12.9863(3)
_cell_measurement_reflns_used    4563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      4.17
_cell_volume                     1264.44(6)
_computing_cell_refinement       'CrysAlis RED (Agilent, 2011)'
_computing_data_collection       'CrysAlis CCD (Agilent, 2011)'
_computing_data_reduction        'CrysAlis RED (Agilent, 2011)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4340
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Gemini R CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31426
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.334
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED (Agilent, 2011)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             658
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.846
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5150
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0534
_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)+(0.0989P)²+0.1443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                3886
_reflns_number_total             5150
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            sf3164.cif
_cod_data_source_block           I
_cod_original_cell_volume        1264.44(5)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2018461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.60314(4) 0.40947(3) 0.53005(3) 0.04638(18) Uani d . 1 1 . .
Cl Cl1 0.55093(13) 0.67789(11) 0.83481(9) 0.0711(3) Uani d . 1 1 . .
Cl Cl2 1.09054(14) 1.02441(9) 0.84931(9) 0.0798(4) Uani d . 1 1 . .
Cl Cl3 0.7025(3) 0.5575(3) 1.06156(15) 0.1492(8) Uani d . 1 1 . .
Cl Cl4 1.2585(3) 0.84339(15) 1.03319(13) 0.1382(7) Uani d . 1 1 . .
O O1 0.7740(3) 0.5084(2) 0.48679(19) 0.0471(6) Uani d . 1 1 . .
O O2 0.9763(3) 0.6699(2) 0.49652(18) 0.0485(6) Uani d . 1 1 . .
O O3 0.5898(3) 0.5492(2) 0.6279(2) 0.0520(6) Uani d . 1 1 . .
O O4 0.7913(3) 0.3679(2) 0.6760(2) 0.0608(7) Uani d . 1 1 . .
O O5 1.0353(3) 0.4738(3) 0.6795(2) 0.0618(7) Uani d . 1 1 . .
H H5O 1.0166 0.4199 0.6221 0.093 Uiso calc R 1 1 . .
O O6 0.6882(4) 0.4162(4) 0.8478(3) 0.0838(15) Uani d PDU 0.807(8) 1 A 1
H H6O 0.6877 0.3774 0.7869 0.126 Uiso calc PR 0.807(8) 1 A 1
O O7 1.1941(11) 0.6603(16) 0.8283(10) 0.083(6) Uani d PDU 0.193(8) 1 A 2
H H7O 1.1726 0.6072 0.7701 0.124 Uiso calc PR 0.193(8) 1 A 2
N N1 0.4294(3) 0.2920(3) 0.5714(3) 0.0517(7) Uani d . 1 1 . .
N N2 0.5849(3) 0.2533(3) 0.4211(2) 0.0479(7) Uani d . 1 1 . .
C C1 0.3560(4) 0.3145(4) 0.6483(4) 0.0630(10) Uani d . 1 1 . .
H H1 0.3840 0.3961 0.6920 0.076 Uiso calc R 1 1 . .
C C2 0.2381(5) 0.2212(5) 0.6669(4) 0.0798(14) Uani d . 1 1 . .
H H2 0.1900 0.2400 0.7231 0.096 Uiso calc R 1 1 . .
C C3 0.1940(5) 0.1026(5) 0.6024(4) 0.0767(13) Uani d . 1 1 . .
H H3 0.1138 0.0402 0.6137 0.092 Uiso calc R 1 1 . .
C C4 0.2676(5) 0.0727(4) 0.5191(4) 0.0669(12) Uani d . 1 1 . .
C C5 0.3864(4) 0.1725(3) 0.5076(3) 0.0530(9) Uani d . 1 1 . .
C C6 0.4694(4) 0.1516(3) 0.4254(3) 0.0514(9) Uani d . 1 1 . .
C C7 0.4320(5) 0.0316(3) 0.3559(3) 0.0608(11) Uani d . 1 1 . .
C C8 0.5189(6) 0.0213(4) 0.2780(4) 0.0742(13) Uani d . 1 1 . .
H H8 0.4984 -0.0562 0.2294 0.089 Uiso calc R 1 1 . .
C C9 0.6329(5) 0.1221(4) 0.2717(4) 0.0700(12) Uani d . 1 1 . .
H H9 0.6892 0.1139 0.2188 0.084 Uiso calc R 1 1 . .
C C10 0.6646(4) 0.2382(4) 0.3454(3) 0.0570(9) Uani d . 1 1 . .
H H10 0.7438 0.3068 0.3415 0.068 Uiso calc R 1 1 . .
C C11 0.3119(6) -0.0679(4) 0.3705(5) 0.0786(15) Uani d . 1 1 . .
H H11 0.2866 -0.1481 0.3250 0.094 Uiso calc R 1 1 . .
C C12 0.2354(6) -0.0496(4) 0.4467(5) 0.0814(15) Uani d . 1 1 . .
H H12 0.1585 -0.1176 0.4540 0.098 Uiso calc R 1 1 . .
C C13 0.8641(4) 0.6201(3) 0.5341(3) 0.0400(7) Uani d . 1 1 . .
C C14 0.8395(3) 0.6933(3) 0.6341(2) 0.0375(7) Uani d . 1 1 . .
C C15 0.7078(4) 0.6523(3) 0.6762(3) 0.0407(7) Uani d . 1 1 . .
C C16 0.7041(4) 0.7285(3) 0.7748(3) 0.0450(8) Uani d . 1 1 . .
C C17 0.8200(5) 0.8419(3) 0.8281(3) 0.0539(9) Uani d . 1 1 . .
H H17 0.8139 0.8906 0.8933 0.065 Uiso calc R 1 1 . .
C C18 0.9439(4) 0.8812(3) 0.7831(3) 0.0508(9) Uani d . 1 1 . .
C C19 0.9560(4) 0.8096(3) 0.6887(3) 0.0452(8) Uani d . 1 1 . .
H H19 1.0417 0.8377 0.6602 0.054 Uiso calc R 1 1 . .
C C20 0.9188(4) 0.4519(3) 0.7214(3) 0.0480(8) Uani d . 1 1 . .
C C21 0.9406(4) 0.5354(3) 0.8310(3) 0.0500(8) Uani d . 1 1 A .
C C22 0.8234(4) 0.5122(3) 0.8889(3) 0.0626(10) Uani d DU 1 1 . .
H H22 0.7311 0.4455 0.8581 0.075 Uiso d PR 0.20 1 A 2
C C23 0.8449(7) 0.5886(6) 0.9909(4) 0.0778(13) Uani d . 1 1 A .
C C24 0.9727(8) 0.6856(5) 1.0346(4) 0.0873(16) Uani d . 1 1 . .
H H24 0.9849 0.7363 1.1036 0.105 Uiso calc R 1 1 A .
C C25 1.0910(7) 0.7138(4) 0.9786(4) 0.0811(14) Uani d . 1 1 A .
C C26 1.0740(5) 0.6359(4) 0.8768(3) 0.0589(10) Uani d DU 1 1 . .
H H26 1.1529 0.6521 0.8399 0.071 Uiso d PR 0.80 1 A 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
O3 Cu O1 . . 93.00(10)
O3 Cu N2 . . 171.97(10)
O1 Cu N2 . . 93.10(11)
O3 Cu N1 . . 91.71(12)
O1 Cu N1 . . 174.85(11)
N2 Cu N1 . . 82.40(13)
O3 Cu O4 . . 93.04(10)
O1 Cu O4 . . 90.90(9)
N2 Cu O4 . . 92.09(10)
N1 Cu O4 . . 86.77(10)
O3 Cu O3 . 2_666 88.44(10)
O1 Cu O3 . 2_666 87.98(9)
N2 Cu O3 . 2_666 86.56(9)
N1 Cu O3 . 2_666 94.22(10)
O4 Cu O3 . 2_666 178.20(7)
O3 Cu Cu . 2_666 54.23(8)
O1 Cu Cu . 2_666 90.05(7)
N2 Cu Cu . 2_666 120.54(8)
N1 Cu Cu . 2_666 94.39(9)
O4 Cu Cu . 2_666 147.25(6)
O3 Cu Cu 2_666 2_666 34.20(5)
C13 O1 Cu . . 128.6(2)
C15 O3 Cu . . 124.1(2)
C20 O4 Cu . . 118.1(2)
C20 O5 H5O . . 109.5
C22 O6 H6O . . 109.5
H6O O6 H22 . . 104.8
C26 O7 H7O . . 109.5
H7O O7 H26 . . 104.7
C1 N1 C5 . . 118.2(3)
C1 N1 Cu . . 129.8(3)
C5 N1 Cu . . 112.0(3)
C10 N2 C6 . . 118.1(3)
C10 N2 Cu . . 128.9(2)
C6 N2 Cu . . 112.9(2)
N1 C1 C2 . . 122.5(4)
N1 C1 H1 . . 118.8
C2 C1 H1 . . 118.8
C3 C2 C1 . . 119.3(5)
C3 C2 H2 . . 120.4
C1 C2 H2 . . 120.4
C2 C3 C4 . . 120.9(4)
C2 C3 H3 . . 119.5
C4 C3 H3 . . 119.5
C3 C4 C5 . . 115.7(4)
C3 C4 C12 . . 126.7(4)
C5 C4 C12 . . 117.6(5)
N1 C5 C4 . . 123.5(4)
N1 C5 C6 . . 116.5(3)
C4 C5 C6 . . 120.0(4)
N2 C6 C7 . . 123.6(4)
N2 C6 C5 . . 116.1(3)
C7 C6 C5 . . 120.2(3)
C8 C7 C6 . . 115.7(4)
C8 C7 C11 . . 125.9(4)
C6 C7 C11 . . 118.4(5)
C9 C8 C7 . . 121.3(4)
C9 C8 H8 . . 119.3
C7 C8 H8 . . 119.3
C8 C9 C10 . . 119.3(5)
C8 C9 H9 . . 120.3
C10 C9 H9 . . 120.3
N2 C10 C9 . . 121.8(4)
N2 C10 H10 . . 119.1
C9 C10 H10 . . 119.1
C12 C11 C7 . . 121.9(4)
C12 C11 H11 . . 119.1
C7 C11 H11 . . 119.1
C11 C12 C4 . . 121.9(4)
C11 C12 H12 . . 119.1
C4 C12 H12 . . 119.1
O2 C13 O1 . . 120.3(3)
O2 C13 C14 . . 118.7(3)
O1 C13 C14 . . 120.9(3)
C15 C14 C19 . . 119.6(3)
C15 C14 C13 . . 123.4(3)
C19 C14 C13 . . 117.0(3)
O3 C15 C16 . . 119.0(3)
O3 C15 C14 . . 123.9(3)
C16 C15 C14 . . 117.1(3)
C17 C16 C15 . . 122.7(3)
C17 C16 Cl1 . . 118.2(3)
C15 C16 Cl1 . . 119.1(3)
C18 C17 C16 . . 118.8(3)
C18 C17 H17 . . 120.6
C16 C17 H17 . . 120.6
C19 C18 C17 . . 121.2(3)
C19 C18 Cl2 . . 119.5(3)
C17 C18 Cl2 . . 119.3(3)
C18 C19 C14 . . 120.6(3)
C18 C19 H19 . . 119.7
C14 C19 H19 . . 119.7
O4 C20 O5 . . 124.1(3)
O4 C20 C21 . . 120.2(3)
O5 C20 C21 . . 115.7(3)
C26 C21 C22 . . 119.1(3)
C26 C21 C20 . . 120.7(3)
C22 C21 C20 . . 120.2(3)
O6 C22 C23 . . 117.7(4)
O6 C22 C21 . . 122.2(3)
C23 C22 C21 . . 120.1(4)
C23 C22 H22 . . 119.9
C21 C22 H22 . . 120.1
C24 C23 C22 . . 120.8(5)
C24 C23 Cl3 . . 119.6(4)
C22 C23 Cl3 . . 119.6(5)
C23 C24 C25 . . 121.0(4)
C23 C24 H24 . . 119.5
C25 C24 H24 . . 119.5
C26 C25 C24 . . 119.3(5)
C26 C25 Cl4 . . 118.9(4)
C24 C25 Cl4 . . 121.8(4)
O7 C26 C21 . . 122.3(7)
O7 C26 C25 . . 117.9(7)
C21 C26 C25 . . 119.7(4)
C21 C26 H26 . . 120.1
C25 C26 H26 . . 120.1
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 O3 . 1.881(2) y
Cu O1 . 1.906(2) y
Cu N2 . 1.990(3) y
Cu N1 . 2.011(3) y
Cu O4 . 2.585(3) y
Cu O3 2_666 2.716(3) y
Cl1 C16 . 1.737(3) ?
Cl2 C18 . 1.748(3) ?
Cl3 C23 . 1.717(5) ?
Cl4 C25 . 1.735(5) ?
O1 C13 . 1.274(4) ?
O2 C13 . 1.257(4) ?
O3 C15 . 1.312(4) ?
O4 C20 . 1.247(4) ?
O5 C20 . 1.267(4) ?
O5 H5O . 0.8200 ?
O6 C22 . 1.3484(10) ?
O6 H6O . 0.8200 ?
O6 H22 . 0.4205 ?
O7 C26 . 1.3494(10) ?
O7 H7O . 0.8200 ?
O7 H26 . 0.4240 ?
N1 C1 . 1.314(5) ?
N1 C5 . 1.361(5) ?
N2 C10 . 1.329(5) ?
N2 C6 . 1.362(4) ?
C1 C2 . 1.390(6) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.355(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.399(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.400(5) ?
C4 C12 . 1.443(7) ?
C5 C6 . 1.428(6) ?
C6 C7 . 1.399(5) ?
C7 C8 . 1.392(7) ?
C7 C11 . 1.421(7) ?
C8 C9 . 1.357(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.394(5) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.319(8) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.479(4) ?
C14 C15 . 1.410(4) ?
C14 C19 . 1.412(4) ?
C15 C16 . 1.402(5) ?
C16 C17 . 1.386(5) ?
C17 C18 . 1.372(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.366(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.486(5) ?
C21 C26 . 1.369(5) ?
C21 C22 . 1.408(5) ?
C22 C23 . 1.375(6) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.316(8) ?
C24 C25 . 1.405(8) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.389(6) ?
C26 H26 . 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
O5 H5O O2 2_766 0.82 1.69 2.489(3) 166
O6 H6O O4 . 0.82 1.85 2.577(5) 147
O7 H7O O5 . 0.82 1.73 2.460(14) 147
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061303
