#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/97/1569756.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_1569756
loop_
_publ_author_name
'Nye, Luke'
'Telfer, Shane G.'
'Turnbull, Mark M.'
_publ_section_title
;
 μ-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,2′-bipyridine)chloridocopper(II)]
 dihydrate
;
_journal_coeditor_code           TK4095
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x230713
_journal_paper_doi               10.1107/S2414314623007137
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          '[Cu2 (C18 H12 O4) Cl2 (C10 H8 N2)2], 2H2 O'
_chemical_formula_moiety         'C38 H28 Cl2 Cu2 N4 O4, 2 (H2 O)'
_chemical_formula_sum            'C38 H32 Cl2 Cu2 N4 O6'
_chemical_formula_weight         838.65
_chemical_name_systematic
'μ-1,6-Dioxo-1,6-diphenylhexane-3,4-diolato-bis[(2,2'-bipyridine)chloridocopper(II)] dihydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                106.426(7)
_cell_angle_beta                 109.090(8)
_cell_angle_gamma                90.373(6)
_cell_formula_units_Z            1
_cell_length_a                   8.7211(2)
_cell_length_b                   10.4194(2)
_cell_length_c                   10.5243(7)
_cell_measurement_reflns_used    3450
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.0
_cell_measurement_theta_min      6.6
_cell_volume                     861.67(9)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2005)
;
_computing_data_reduction
;
PROCESS-AUTO (Rigaku, 1998)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'confocal optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7470
_diffrn_reflns_theta_full        61.131
_diffrn_reflns_theta_max         61.131
_diffrn_reflns_theta_min         6.618
_exptl_absorpt_coefficient_mu    3.409
_exptl_absorpt_correction_T_max  0.9286
_exptl_absorpt_correction_T_min  0.6408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Rigaku, 1995)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0514P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                1901
_reflns_number_total             2552
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tk4095.cif
_cod_data_source_block           I
_cod_original_cell_volume        861.67(8)
_cod_database_code               1569756
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.666
_shelx_estimated_absorpt_t_max   0.935
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.33000(7) 0.32164(6) 0.96525(6) 0.0307(2) Uani d 1 . .
Cl Cl1 0.11639(12) 0.13154(10) 0.77171(10) 0.0345(3) Uani d 1 . .
O O1 0.1754(3) 0.4177(3) 1.0408(3) 0.0324(7) Uani d 1 . .
C C1 0.0704(5) 0.4796(4) 0.9723(4) 0.0254(10) Uani d 1 . .
C C2 0.0728(5) 0.5143(4) 0.8569(4) 0.0294(10) Uani d 1 . .
H H2 -0.017613 0.555390 0.812000 0.035 Uiso calc 1 . .
O O3 0.3211(3) 0.4301(3) 0.8421(3) 0.0330(7) Uani d 1 . .
C C3 0.2001(5) 0.4937(4) 0.7987(4) 0.0271(10) Uani d 1 . .
C C4 0.1975(5) 0.5506(4) 0.6837(4) 0.0303(10) Uani d 1 . .
C C5 0.2992(5) 0.5074(4) 0.6059(4) 0.0329(11) Uani d 1 . .
H H5 0.372026 0.443341 0.628745 0.039 Uiso calc 1 . .
C C6 0.2963(5) 0.5555(5) 0.4963(5) 0.0411(12) Uani d 1 . .
H H6 0.365425 0.523306 0.443454 0.049 Uiso calc 1 . .
C C7 0.1939(6) 0.6503(5) 0.4627(5) 0.0422(12) Uani d 1 . .
H H7 0.193055 0.683511 0.387222 0.051 Uiso calc 1 . .
C C8 0.0922(5) 0.6969(4) 0.5389(5) 0.0393(12) Uani d 1 . .
H H8 0.022438 0.763064 0.516788 0.047 Uiso calc 1 . .
C C9 0.0926(5) 0.6469(4) 0.6470(4) 0.0310(10) Uani d 1 . .
H H9 0.020939 0.677797 0.697730 0.037 Uiso calc 1 . .
N N11 0.5341(4) 0.2451(3) 0.9445(3) 0.0282(8) Uani d 1 . .
C C11 0.6014(5) 0.2564(4) 0.8501(4) 0.0339(11) Uani d 1 . .
H H11 0.549680 0.303493 0.785150 0.041 Uiso calc 1 . .
C C12 0.7425(5) 0.2020(4) 0.8441(4) 0.0343(11) Uani d 1 . .
H H12 0.788780 0.212980 0.777127 0.041 Uiso calc 1 . .
C C13 0.8170(5) 0.1309(4) 0.9368(4) 0.0302(10) Uani d 1 . .
H H13 0.914522 0.092053 0.933922 0.036 Uiso calc 1 . .
C C14 0.7475(5) 0.1177(4) 1.0326(4) 0.0277(10) Uani d 1 . .
H H14 0.796296 0.069566 1.097313 0.033 Uiso calc 1 . .
C C15 0.6054(5) 0.1754(4) 1.0339(4) 0.0237(9) Uani d 1 . .
C C16 0.5227(5) 0.1699(4) 1.1351(4) 0.0275(10) Uani d 1 . .
C C17 0.5733(5) 0.1040(4) 1.2364(4) 0.0273(10) Uani d 1 . .
H H17 0.667767 0.057482 1.244906 0.033 Uiso calc 1 . .
C C18 0.4850(5) 0.1061(4) 1.3261(4) 0.0318(11) Uani d 1 . .
H H18 0.519826 0.063659 1.398103 0.038 Uiso calc 1 . .
C C19 0.3447(5) 0.1721(4) 1.3075(4) 0.0362(11) Uani d 1 . .
H H19 0.280783 0.173765 1.365635 0.043 Uiso calc 1 . .
C C20 0.2994(5) 0.2349(4) 1.2041(4) 0.0316(11) Uani d 1 . .
H H20 0.203908 0.280215 1.193139 0.038 Uiso calc 1 . .
N N12 0.3846(4) 0.2349(3) 1.1175(3) 0.0282(8) Uani d 1 . .
O O2 0.2128(4) 0.0355(4) 0.4911(4) 0.0538(10) Uani d 1 . .
H H2A 0.178(6) 0.059(5) 0.557(5) 0.065 Uiso d 1 . .
H H2B 0.110(6) -0.013(4) 0.420(5) 0.065 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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 Cu1 O3 . . 93.44(11) ?
O1 Cu1 N12 . . 89.27(12) ?
O3 Cu1 N12 . . 167.52(12) ?
O1 Cu1 N11 . . 163.37(13) ?
O3 Cu1 N11 . . 93.59(12) ?
N12 Cu1 N11 . . 80.78(13) ?
O1 Cu1 Cl1 . . 95.59(9) ?
O3 Cu1 Cl1 . . 94.10(9) ?
N12 Cu1 Cl1 . . 97.76(10) ?
N11 Cu1 Cl1 . . 98.92(9) ?
C1 O1 Cu1 . . 122.0(2) ?
O1 C1 C2 . . 126.3(4) ?
O1 C1 C1 . 2_567 115.8(4) ?
C2 C1 C1 . 2_567 117.8(5) ?
C1 C2 C3 . . 125.1(4) ?
C1 C2 H2 . . 117.4 ?
C3 C2 H2 . . 117.4 ?
C3 O3 Cu1 . . 123.6(3) ?
O3 C3 C2 . . 123.4(4) ?
O3 C3 C4 . . 116.9(4) ?
C2 C3 C4 . . 119.7(4) ?
C5 C4 C9 . . 117.5(4) ?
C5 C4 C3 . . 119.9(4) ?
C9 C4 C3 . . 122.6(4) ?
C6 C5 C4 . . 121.2(4) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 120.5(4) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C6 C7 C8 . . 119.9(4) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 119.7(4) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C8 C9 C4 . . 121.2(4) ?
C8 C9 H9 . . 119.4 ?
C4 C9 H9 . . 119.4 ?
C11 N11 C15 . . 118.8(3) ?
C11 N11 Cu1 . . 125.9(3) ?
C15 N11 Cu1 . . 115.3(3) ?
N11 C11 C12 . . 122.1(4) ?
N11 C11 H11 . . 118.9 ?
C12 C11 H11 . . 118.9 ?
C11 C12 C13 . . 119.3(4) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C14 C13 C12 . . 118.9(4) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C13 C14 C15 . . 119.1(4) ?
C13 C14 H14 . . 120.4 ?
C15 C14 H14 . . 120.4 ?
N11 C15 C14 . . 121.9(4) ?
N11 C15 C16 . . 114.7(3) ?
C14 C15 C16 . . 123.5(4) ?
N12 C16 C17 . . 121.7(4) ?
N12 C16 C15 . . 113.3(3) ?
C17 C16 C15 . . 125.0(3) ?
C16 C17 C18 . . 119.7(4) ?
C16 C17 H17 . . 120.2 ?
C18 C17 H17 . . 120.2 ?
C19 C18 C17 . . 118.3(4) ?
C19 C18 H18 . . 120.8 ?
C17 C18 H18 . . 120.8 ?
C20 C19 C18 . . 119.4(4) ?
C20 C19 H19 . . 120.3 ?
C18 C19 H19 . . 120.3 ?
N12 C20 C19 . . 122.9(4) ?
N12 C20 H20 . . 118.5 ?
C19 C20 H20 . . 118.5 ?
C20 N12 C16 . . 118.0(4) ?
C20 N12 Cu1 . . 126.2(3) ?
C16 N12 Cu1 . . 115.9(3) ?
H2A O2 H2B . . 96(4) ?
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 O1 . 1.929(3) ?
Cu1 O3 . 1.930(3) ?
Cu1 N12 . 1.984(3) ?
Cu1 N11 . 2.006(3) ?
Cu1 Cl1 . 2.5944(12) ?
O1 C1 . 1.270(4) ?
C1 C2 . 1.369(5) ?
C1 C1 2_567 1.537(7) ?
C2 C3 . 1.424(5) ?
C2 H2 . 0.9500 ?
O3 C3 . 1.275(4) ?
C3 C4 . 1.485(5) ?
C4 C5 . 1.390(5) ?
C4 C9 . 1.412(5) ?
C5 C6 . 1.374(6) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.378(6) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.385(6) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.378(5) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
N11 C11 . 1.338(5) ?
N11 C15 . 1.345(5) ?
C11 C12 . 1.371(5) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.387(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.372(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.383(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.481(5) ?
C16 N12 . 1.371(5) ?
C16 C17 . 1.384(5) ?
C17 C18 . 1.396(5) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.393(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.375(5) ?
C19 H19 . 0.9500 ?
C20 N12 . 1.352(5) ?
C20 H20 . 0.9500 ?
O2 H2A . 0.82(5) ?
O2 H2B . 0.98(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
_geom_hbond_publ_flag
O2 H2A Cl1 . 0.82(5) 2.41(5) 3.224(3) 171(5) yes
O2 H2B Cl1 2_556 0.98(4) 2.33(5) 3.307(4) 172(4) yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 O1 C1 C2 . . . . -16.0(6) ?
Cu1 O1 C1 C1 . . . 2_567 165.1(3) ?
O1 C1 C2 C3 . . . . -4.0(7) ?
C1 C1 C2 C3 2_567 . . . 174.9(4) ?
Cu1 O3 C3 C2 . . . . 12.9(5) ?
Cu1 O3 C3 C4 . . . . -168.5(2) ?
C1 C2 C3 O3 . . . . 5.8(6) ?
C1 C2 C3 C4 . . . . -172.7(4) ?
O3 C3 C4 C5 . . . . 15.4(6) ?
C2 C3 C4 C5 . . . . -166.0(4) ?
O3 C3 C4 C9 . . . . -165.8(4) ?
C2 C3 C4 C9 . . . . 12.9(6) ?
C9 C4 C5 C6 . . . . -0.7(6) ?
C3 C4 C5 C6 . . . . 178.2(4) ?
C4 C5 C6 C7 . . . . 1.2(7) ?
C5 C6 C7 C8 . . . . -0.4(7) ?
C6 C7 C8 C9 . . . . -0.8(6) ?
C7 C8 C9 C4 . . . . 1.3(6) ?
C5 C4 C9 C8 . . . . -0.6(6) ?
C3 C4 C9 C8 . . . . -179.4(4) ?
C15 N11 C11 C12 . . . . -1.7(6) ?
Cu1 N11 C11 C12 . . . . 179.3(3) ?
N11 C11 C12 C13 . . . . 1.2(6) ?
C11 C12 C13 C14 . . . . -0.4(6) ?
C12 C13 C14 C15 . . . . 0.1(6) ?
C11 N11 C15 C14 . . . . 1.3(6) ?
Cu1 N11 C15 C14 . . . . -179.5(3) ?
C11 N11 C15 C16 . . . . 179.4(3) ?
Cu1 N11 C15 C16 . . . . -1.4(4) ?
C13 C14 C15 N11 . . . . -0.6(6) ?
C13 C14 C15 C16 . . . . -178.5(4) ?
N11 C15 C16 N12 . . . . 1.4(5) ?
C14 C15 C16 N12 . . . . 179.5(3) ?
N11 C15 C16 C17 . . . . 179.8(4) ?
C14 C15 C16 C17 . . . . -2.1(6) ?
N12 C16 C17 C18 . . . . -1.8(6) ?
C15 C16 C17 C18 . . . . 179.9(4) ?
C16 C17 C18 C19 . . . . 1.8(6) ?
C17 C18 C19 C20 . . . . -1.3(6) ?
C18 C19 C20 N12 . . . . 0.6(6) ?
C19 C20 N12 C16 . . . . -0.4(6) ?
C19 C20 N12 Cu1 . . . . 179.9(3) ?
C17 C16 N12 C20 . . . . 1.0(6) ?
C15 C16 N12 C20 . . . . 179.5(3) ?
C17 C16 N12 Cu1 . . . . -179.2(3) ?
C15 C16 N12 Cu1 . . . . -0.7(4) ?
