#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/97/1569757.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_1569757
loop_
_publ_author_name
'Jia, Jason'
'LaDuca, Robert L.'
_publ_section_title
;
 Poly[[μ-1,4-bis(pyridin-4-ylmethyl)piperazine]bis[μ3-4-(2-carboxylatoethyl)benzoato]dicopper(II)]
;
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x230745
_journal_paper_doi               10.1107/S2414314623007459
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          '[Cu2 (C9 H6 O4)2 (C16 H20 N4)]'
_chemical_formula_moiety         'C34 H32 Cu2 N4 O8'
_chemical_formula_sum            'C34 H32 Cu2 N4 O8'
_chemical_formula_weight         751.71
_chemical_name_systematic
Poly[[μ-1,4-bis(pyridin-4-ylmethyl)piperazine]bis[μ₃-4-(2-carboxylatoethyl)benzoato]dicopper(II)]
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_cell_angle_alpha                104.5230(10)
_cell_angle_beta                 93.0490(10)
_cell_angle_gamma                99.9660(10)
_cell_formula_units_Z            1
_cell_length_a                   8.5431(8)
_cell_length_b                   9.7391(9)
_cell_length_c                   9.9667(9)
_cell_measurement_reflns_used    5378
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.20
_cell_volume                     786.57(13)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
COSMO (Bruker 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
CrystalMakerX (Palmer, 2020)
;
_computing_publication_material
;
OLEX2  (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_min         2.122
_diffrn_source                   'sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.412
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       plate
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.068
_refine_diff_density_max         1.530
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0442
_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)+(0.0559P)²+0.6812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                2459
_reflns_number_total             2883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm4195.cif
_cod_data_source_block           I
_cod_database_code               1569757
#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   0.764
_shelx_estimated_absorpt_t_max   0.910
#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 0.15932(5) 0.57426(4) 1.06176(4) 0.02211(16) Uani d 1 . .
O O1 0.2117(3) 0.4082(2) 0.9252(2) 0.0217(5) Uani d 1 . .
O O2 -0.0365(3) 0.2769(2) 0.8582(2) 0.0234(5) Uani d 1 . .
O O3 0.3034(3) 0.5715(3) 0.2622(2) 0.0254(6) Uani d 1 . .
O O4 0.0605(3) 0.4498(2) 0.1767(2) 0.0243(5) Uani d 1 . .
N N1 0.3031(3) 0.7066(3) 0.9800(3) 0.0227(6) Uani d 1 . .
N N2 0.5273(3) 0.9828(3) 0.6389(3) 0.0212(6) Uani d 1 . .
C C1 0.1118(4) 0.3055(3) 0.8481(3) 0.0201(7) Uani d 1 . .
C C2 0.1732(4) 0.2095(4) 0.7247(3) 0.0226(7) Uani d 1 . .
H H2A 0.283116 0.198415 0.750049 0.027 Uiso calc 1 . .
H H2B 0.103647 0.112435 0.695960 0.027 Uiso calc 1 . .
C C3 0.1715(4) 0.2823(4) 0.6072(3) 0.0202(7) Uani d 1 . .
C C4 0.2935(4) 0.3977(4) 0.6063(4) 0.0237(8) Uani d 1 . .
H H4 0.377601 0.430724 0.679879 0.028 Uiso calc 1 . .
C C5 0.2926(4) 0.4638(4) 0.4992(3) 0.0224(7) Uani d 1 . .
H H5 0.376877 0.541559 0.499491 0.027 Uiso calc 1 . .
C C6 0.1706(4) 0.4188(3) 0.3911(3) 0.0206(7) Uani d 1 . .
C C7 0.0445(4) 0.3072(4) 0.3944(4) 0.0262(8) Uani d 1 . .
H H7 -0.042266 0.277462 0.323303 0.031 Uiso calc 1 . .
C C8 0.0466(4) 0.2403(4) 0.5012(4) 0.0255(8) Uani d 1 . .
H H8 -0.039000 0.164151 0.502236 0.031 Uiso calc 1 . .
C C9 0.1809(4) 0.4860(4) 0.2720(3) 0.0217(7) Uani d 1 . .
C C10 0.2529(4) 0.8020(4) 0.9196(3) 0.0235(7) Uani d 1 . .
H H10 0.147482 0.819245 0.929866 0.028 Uiso calc 1 . .
C C11 0.3479(4) 0.8759(4) 0.8433(3) 0.0238(8) Uani d 1 . .
H H11 0.307795 0.943106 0.802968 0.029 Uiso calc 1 . .
C C12 0.5025(4) 0.8526(4) 0.8249(3) 0.0221(7) Uani d 1 . .
C C13 0.5560(4) 0.7578(4) 0.8919(4) 0.0267(8) Uani d 1 . .
H H13 0.661744 0.740613 0.885116 0.032 Uiso calc 1 . .
C C14 0.4550(4) 0.6888(4) 0.9684(4) 0.0258(8) Uani d 1 . .
H H14 0.494412 0.625784 1.014908 0.031 Uiso calc 1 . .
C C15 0.6109(4) 0.9265(4) 0.7382(4) 0.0259(8) Uani d 1 . .
H H15A 0.688256 1.007259 0.801480 0.031 Uiso calc 1 . .
H H15B 0.672420 0.856634 0.686588 0.031 Uiso calc 1 . .
C C16 0.6446(4) 1.0736(3) 0.5796(4) 0.0226(7) Uani d 1 . .
H H16A 0.719702 1.015295 0.532433 0.027 Uiso calc 1 . .
H H16B 0.706851 1.153652 0.655442 0.027 Uiso calc 1 . .
C C17 0.4372(4) 0.8651(4) 0.5234(4) 0.0235(7) Uani d 1 . .
H H17A 0.356366 0.802431 0.560496 0.028 Uiso calc 1 . .
H H17B 0.510889 0.805222 0.475975 0.028 Uiso calc 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'
Cu Cu 0.3201 1.2651 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 1.00 0.0600
1.00 -1.00 -1.00 0.0510
0.00 0.00 1.00 0.0320
0.00 0.00 -1.00 0.0250
1.00 -1.00 2.00 0.0340
-1.00 1.00 -2.00 0.0310
-1.00 2.00 2.00 0.0380
1.00 -2.00 -2.00 0.0420
0.00 1.00 2.00 0.0310
0.00 -1.00 -2.00 0.0340
1.00 2.00 2.00 0.0410
-1.00 -2.00 -2.00 0.0600
2.00 -1.00 1.00 0.0620
-1.00 2.00 0.00 0.0440
-2.00 -1.00 -1.00 0.0790
0.00 1.00 0.00 0.0450
0.00 -1.00 0.00 0.0620
-2.00 -1.00 2.00 0.0920
1.00 2.00 -2.00 0.0800
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 . 1_556 101.92(9) y
O1 Cu1 O4 . 1_556 92.30(10) y
O1 Cu1 N1 . . 89.47(11) y
O2 Cu1 O1 2_567 . 157.53(10) y
O2 Cu1 O3 2_567 1_556 99.04(9) y
O2 Cu1 O4 2_567 1_556 90.56(10) y
O2 Cu1 N1 2_567 . 93.02(11) y
O4 Cu1 O3 1_556 1_556 61.65(9) y
N1 Cu1 O3 . 1_556 104.62(10) y
N1 Cu1 O4 . 1_556 166.22(11) y
C1 O1 Cu1 . . 125.2(2) ?
C1 O2 Cu1 . 2_567 122.9(2) ?
C9 O3 Cu1 . 1_554 82.5(2) ?
C9 O4 Cu1 . 1_554 95.0(2) ?
C10 N1 Cu1 . . 123.5(2) ?
C10 N1 C14 . . 117.3(3) ?
C14 N1 Cu1 . . 118.7(2) ?
C15 N2 C16 . . 109.1(3) ?
C15 N2 C17 . . 111.4(3) ?
C16 N2 C17 . . 108.0(3) ?
O1 C1 O2 . . 126.7(3) ?
O1 C1 C2 . . 116.9(3) ?
O2 C1 C2 . . 116.3(3) ?
C1 C2 H2A . . 110.3 ?
C1 C2 H2B . . 110.3 ?
H2A C2 H2B . . 108.6 ?
C3 C2 C1 . . 107.1(3) ?
C3 C2 H2A . . 110.3 ?
C3 C2 H2B . . 110.3 ?
C4 C3 C2 . . 120.2(3) ?
C8 C3 C2 . . 121.3(3) ?
C8 C3 C4 . . 118.5(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 C3 . . 120.3(3) ?
C5 C4 H4 . . 119.8 ?
C4 C5 H5 . . 119.4 ?
C4 C5 C6 . . 121.2(3) ?
C6 C5 H5 . . 119.4 ?
C5 C6 C7 . . 118.8(3) ?
C5 C6 C9 . . 119.3(3) ?
C7 C6 C9 . . 121.9(3) ?
C6 C7 H7 . . 120.1 ?
C8 C7 C6 . . 119.9(3) ?
C8 C7 H7 . . 120.1 ?
C3 C8 H8 . . 119.3 ?
C7 C8 C3 . . 121.3(3) ?
C7 C8 H8 . . 119.3 ?
O3 C9 Cu1 . 1_554 67.55(18) ?
O3 C9 O4 . . 120.8(3) ?
O3 C9 C6 . . 120.8(3) ?
O4 C9 Cu1 . 1_554 53.30(16) ?
O4 C9 C6 . . 118.3(3) ?
C6 C9 Cu1 . 1_554 171.6(3) ?
N1 C10 H10 . . 118.7 ?
N1 C10 C11 . . 122.6(3) ?
C11 C10 H10 . . 118.7 ?
C10 C11 H11 . . 119.8 ?
C10 C11 C12 . . 120.3(3) ?
C12 C11 H11 . . 119.8 ?
C11 C12 C15 . . 122.9(3) ?
C13 C12 C11 . . 116.8(3) ?
C13 C12 C15 . . 120.3(3) ?
C12 C13 H13 . . 120.1 ?
C14 C13 C12 . . 119.8(3) ?
C14 C13 H13 . . 120.1 ?
N1 C14 C13 . . 123.0(3) ?
N1 C14 H14 . . 118.5 ?
C13 C14 H14 . . 118.5 ?
N2 C15 C12 . . 114.2(3) ?
N2 C15 H15A . . 108.7 ?
N2 C15 H15B . . 108.7 ?
C12 C15 H15A . . 108.7 ?
C12 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
N2 C16 H16A . . 109.5 ?
N2 C16 H16B . . 109.5 ?
N2 C16 C17 . 2_676 110.8(3) ?
H16A C16 H16B . . 108.1 ?
C17 C16 H16A 2_676 . 109.5 ?
C17 C16 H16B 2_676 . 109.5 ?
N2 C17 C16 . 2_676 110.2(3) ?
N2 C17 H17A . . 109.6 ?
N2 C17 H17B . . 109.6 ?
C16 C17 H17A 2_676 . 109.6 ?
C16 C17 H17B 2_676 . 109.6 ?
H17A C17 H17B . . 108.1 ?
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
Cu1 Cu1 2_567 2.8992(8) ?
Cu1 O1 . 1.969(2) y
Cu1 O2 2_567 1.968(2) y
Cu1 O3 1_556 2.299(2) y
Cu1 O4 1_556 1.985(2) y
Cu1 N1 . 1.979(3) y
Cu1 C9 1_556 2.466(3) ?
O1 C1 . 1.252(4) ?
O2 C1 . 1.264(4) ?
O3 C9 . 1.244(4) ?
O4 C9 . 1.299(4) ?
N1 C10 . 1.343(4) ?
N1 C14 . 1.346(4) ?
N2 C15 . 1.458(4) ?
N2 C16 . 1.467(4) ?
N2 C17 . 1.473(4) ?
C1 C2 . 1.525(4) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C2 C3 . 1.514(5) ?
C3 C4 . 1.396(5) ?
C3 C8 . 1.391(5) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.378(5) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.388(5) ?
C6 C7 . 1.400(5) ?
C6 C9 . 1.492(5) ?
C7 H7 . 0.9500 ?
C7 C8 . 1.381(5) ?
C8 H8 . 0.9500 ?
C10 H10 . 0.9500 ?
C10 C11 . 1.375(5) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.392(5) ?
C12 C13 . 1.389(5) ?
C12 C15 . 1.513(5) ?
C13 H13 . 0.9500 ?
C13 C14 . 1.380(5) ?
C14 H14 . 0.9500 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C16 C17 2_676 1.508(5) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
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 O2 . . . . -12.1(5) ?
Cu1 O1 C1 C2 . . . . 164.4(2) ?
Cu1 O2 C1 O1 2_567 . . . 28.1(4) ?
Cu1 O2 C1 C2 2_567 . . . -148.4(2) ?
Cu1 O3 C9 O4 1_554 . . . 1.2(3) ?
Cu1 O3 C9 C6 1_554 . . . 179.2(3) ?
Cu1 O4 C9 O3 1_554 . . . -1.4(3) ?
Cu1 O4 C9 C6 1_554 . . . -179.5(2) ?
Cu1 N1 C10 C11 . . . . -168.9(2) ?
Cu1 N1 C14 C13 . . . . 168.5(3) ?
O1 C1 C2 C3 . . . . -84.4(3) ?
O2 C1 C2 C3 . . . . 92.4(3) ?
N1 C10 C11 C12 . . . . 0.5(5) ?
C1 C2 C3 C4 . . . . 79.3(4) ?
C1 C2 C3 C8 . . . . -98.3(4) ?
C2 C3 C4 C5 . . . . 179.7(3) ?
C2 C3 C8 C7 . . . . 179.7(3) ?
C3 C4 C5 C6 . . . . 0.6(5) ?
C4 C3 C8 C7 . . . . 2.1(5) ?
C4 C5 C6 C7 . . . . 2.0(5) ?
C4 C5 C6 C9 . . . . -175.4(3) ?
C5 C6 C7 C8 . . . . -2.6(5) ?
C5 C6 C9 O3 . . . . 6.7(5) ?
C5 C6 C9 O4 . . . . -175.2(3) ?
C6 C7 C8 C3 . . . . 0.5(5) ?
C7 C6 C9 O3 . . . . -170.6(3) ?
C7 C6 C9 O4 . . . . 7.4(5) ?
C8 C3 C4 C5 . . . . -2.7(5) ?
C9 C6 C7 C8 . . . . 174.8(3) ?
C10 N1 C14 C13 . . . . -3.5(5) ?
C10 C11 C12 C13 . . . . -2.8(5) ?
C10 C11 C12 C15 . . . . 177.8(3) ?
C11 C12 C13 C14 . . . . 2.0(5) ?
C11 C12 C15 N2 . . . . -20.0(5) ?
C12 C13 C14 N1 . . . . 1.2(5) ?
C13 C12 C15 N2 . . . . 160.6(3) ?
C14 N1 C10 C11 . . . . 2.6(5) ?
C15 N2 C16 C17 . . . 2_676 -179.7(3) ?
C15 N2 C17 C16 . . . 2_676 -178.5(3) ?
C15 C12 C13 C14 . . . . -178.7(3) ?
C16 N2 C15 C12 . . . . 169.9(3) ?
C16 N2 C17 C16 . . . 2_676 -58.8(4) ?
C17 N2 C15 C12 . . . . -71.1(4) ?
C17 N2 C16 C17 . . . 2_676 59.2(4) ?
