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#$Date: 2023-07-05 13:08:29 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246768.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246768
loop_
_publ_author_name
'Klongdee, Fatima'
'Chainok, Kittipong'
'Youngme, Sujittra'
'Boonmak, Jaursup'
_publ_section_title
;
 Variations in the structural composition of pyrazole-3,5-dicarboxylato
 Cu(ii) complexes with 1,2-di(4-pyridyl)ethane synthesized under different
 conditions
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              3628
_journal_page_last               3636
_journal_paper_doi               10.1039/D3CE00384A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C22 H22 Cu3 N6 O12'
_chemical_formula_sum            'C22 H22 Cu3 N6 O12'
_chemical_formula_weight         753.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-11-04 deposited with the CCDC.	2023-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.716(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2018(7)
_cell_length_b                   10.6192(6)
_cell_length_c                   12.7553(9)
_cell_measurement_reflns_used    3583
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.6395
_cell_measurement_theta_min      2.933
_cell_volume                     1243.77(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       BrukerAPEX2
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    SHELXL
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker D8 QUEST PHOTON 100
;
_diffrn_measurement_method       '\fandω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1689
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30891
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_min         2.933
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.623
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_description       polygon
_exptl_crystal_F_000             758
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0427
_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)+(0.0367P)²+1.7805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1806
_reflns_number_total             2446
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00384a2.cif
_cod_data_source_block           compound3
_cod_depositor_comments
'Adding full bibliography for 7246767--7246772.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246768
_shelx_shelxl_version_number     2014/7
_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   0.694
_shelx_estimated_absorpt_t_max   0.880
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.37330(5) 0.58078(5) 0.72265(4) 0.02057(17) Uani 1 1 d . . . . .
Cu2 Cu 0.0000 0.5000 0.5000 0.0317(2) Uani 1 2 d S . P . .
O1 O 0.3773(3) 0.7355(3) 0.8124(2) 0.0277(7) Uani 1 1 d . . . . .
O2 O 0.2261(3) 0.8677(3) 0.8877(2) 0.0351(8) Uani 1 1 d . . . . .
O3 O -0.1652(3) 0.6124(3) 0.4828(2) 0.0295(8) Uani 1 1 d . . . . .
O4 O -0.2843(3) 0.7608(3) 0.5666(2) 0.0284(7) Uani 1 1 d . . . . .
O5 O 0.3507(4) 0.3999(3) 0.6803(2) 0.0270(7) Uani 1 1 d D . . . .
O6 O 0.4463(4) 0.6268(4) 0.5651(3) 0.0371(8) Uani 1 1 d D . . . .
N1 N 0.1712(4) 0.6381(3) 0.6871(3) 0.0193(8) Uani 1 1 d . . . . .
N2 N 0.0583(4) 0.6147(3) 0.6169(3) 0.0213(8) Uani 1 1 d . . . . .
N3 N 0.5566(4) 0.5332(3) 0.8010(3) 0.0199(8) Uani 1 1 d . . . . .
C1 C 0.2515(5) 0.7877(4) 0.8221(3) 0.0230(10) Uani 1 1 d . . . . .
C2 C 0.1368(4) 0.7402(4) 0.7437(3) 0.0184(9) Uani 1 1 d . . . . .
C3 C -0.0013(4) 0.7826(4) 0.7122(3) 0.0200(9) Uani 1 1 d . . . . .
H3 H -0.0523 0.8495 0.7392 0.024 Uiso 1 1 calc R U . . .
C4 C -0.0454(4) 0.7024(4) 0.6313(3) 0.0188(9) Uani 1 1 d . . . . .
C5 C -0.1765(4) 0.6946(4) 0.5573(3) 0.0218(10) Uani 1 1 d . . . . .
C6 C 0.6796(5) 0.5963(4) 0.7907(3) 0.0266(10) Uani 1 1 d . . . . .
H6 H 0.6828 0.6560 0.7376 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8025(5) 0.5762(4) 0.8560(4) 0.0274(10) Uani 1 1 d . . . . .
H7 H 0.8870 0.6214 0.8459 0.033 Uiso 1 1 calc R U . . .
C8 C 0.8011(4) 0.4900(4) 0.9357(3) 0.0177(9) Uani 1 1 d . . . . .
C9 C 0.6751(4) 0.4244(4) 0.9448(3) 0.0241(10) Uani 1 1 d . . . . .
H9 H 0.6698 0.3645 0.9975 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5558(5) 0.4461(4) 0.8766(3) 0.0269(11) Uani 1 1 d . . . . .
H10 H 0.4719 0.3988 0.8834 0.032 Uiso 1 1 calc R U . . .
C11 C 0.9305(4) 0.4681(4) 1.0129(3) 0.0218(9) Uani 1 1 d . . . . .
H11A H 0.9051 0.4965 1.0816 0.026 Uiso 1 1 calc R U . . .
H11B H 0.9483 0.3781 1.0176 0.026 Uiso 1 1 calc R U . . .
H2 H 0.429(3) 0.361(5) 0.669(4) 0.07(2) Uiso 1 1 d D . . . .
H1 H 0.300(4) 0.383(5) 0.624(2) 0.058(18) Uiso 1 1 d D . . . .
H5 H 0.406(5) 0.615(5) 0.5039(18) 0.058(19) Uiso 1 1 d D . . . .
H4 H 0.519(4) 0.672(5) 0.550(4) 0.07(2) Uiso 1 1 d D . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N1 162.76(14) . . ?
N3 Cu1 O1 86.37(13) . . ?
N1 Cu1 O1 82.01(12) . . ?
N3 Cu1 O5 87.80(13) . . ?
N1 Cu1 O5 98.83(13) . . ?
O1 Cu1 O5 159.95(14) . . ?
N3 Cu1 O6 102.51(14) . . ?
N1 Cu1 O6 93.45(14) . . ?
O1 Cu1 O6 110.05(14) . . ?
O5 Cu1 O6 89.94(14) . . ?
O3 Cu2 O3 180.0 3_566 . ?
O3 Cu2 N2 82.99(13) 3_566 3_566 ?
O3 Cu2 N2 97.01(13) . 3_566 ?
O3 Cu2 N2 97.01(13) 3_566 . ?
O3 Cu2 N2 82.99(13) . . ?
N2 Cu2 N2 180.00(13) 3_566 . ?
C1 O1 Cu1 115.0(3) . . ?
C5 O3 Cu2 115.6(2) . . ?
Cu1 O5 H2 116(4) . . ?
Cu1 O5 H1 118(4) . . ?
H2 O5 H1 100.1(15) . . ?
Cu1 O6 H5 132(3) . . ?
Cu1 O6 H4 128(3) . . ?
H5 O6 H4 100.2(15) . . ?
N2 N1 C2 107.8(3) . . ?
N2 N1 Cu1 140.0(3) . . ?
C2 N1 Cu1 111.9(2) . . ?
N1 N2 C4 107.6(3) . . ?
N1 N2 Cu2 140.8(3) . . ?
C4 N2 Cu2 111.5(3) . . ?
C6 N3 C10 117.7(4) . . ?
C6 N3 Cu1 121.8(3) . . ?
C10 N3 Cu1 119.9(3) . . ?
O2 C1 O1 124.9(4) . . ?
O2 C1 C2 122.2(4) . . ?
O1 C1 C2 112.8(4) . . ?
N1 C2 C3 110.4(3) . . ?
N1 C2 C1 116.7(4) . . ?
C3 C2 C1 132.9(4) . . ?
C4 C3 C2 103.7(4) . . ?
C4 C3 H3 128.2 . . ?
C2 C3 H3 128.2 . . ?
N2 C4 C3 110.5(4) . . ?
N2 C4 C5 115.3(4) . . ?
C3 C4 C5 134.2(4) . . ?
O4 C5 O3 124.0(4) . . ?
O4 C5 C4 122.3(4) . . ?
O3 C5 C4 113.6(4) . . ?
N3 C6 C7 122.2(4) . . ?
N3 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 117.0(4) . . ?
C9 C8 C11 120.2(4) . . ?
C7 C8 C11 122.8(4) . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N3 C10 C9 122.0(4) . . ?
N3 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C11 C11 C8 115.7(4) 3_767 . ?
C11 C11 H11A 108.4 3_767 . ?
C8 C11 H11A 108.4 . . ?
C11 C11 H11B 108.4 3_767 . ?
C8 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.970(3) . ?
Cu1 N1 1.981(3) . ?
Cu1 O1 2.001(3) . ?
Cu1 O5 2.003(3) . ?
Cu1 O6 2.214(3) . ?
Cu2 O3 1.934(3) 3_566 ?
Cu2 O3 1.934(3) . ?
Cu2 N2 1.973(3) 3_566 ?
Cu2 N2 1.973(3) . ?
O1 C1 1.297(5) . ?
O2 C1 1.225(5) . ?
O3 C5 1.299(5) . ?
O4 C5 1.227(5) . ?
O5 H2 0.851(10) . ?
O5 H1 0.849(10) . ?
O6 H5 0.851(10) . ?
O6 H4 0.852(10) . ?
N1 N2 1.349(4) . ?
N1 C2 1.352(5) . ?
N2 C4 1.354(5) . ?
N3 C6 1.329(6) . ?
N3 C10 1.337(5) . ?
C1 C2 1.494(5) . ?
C2 C3 1.383(6) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.485(5) . ?
C6 C7 1.377(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(6) . ?
C8 C11 1.513(5) . ?
C9 C10 1.375(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C11 1.503(8) 3_767 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
