#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:08:29 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246770.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_7246770
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_sum            'C22 H16 Cu2 N6 O8'
_chemical_formula_weight         619.49
_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   geom
_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                 90.841(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5089(10)
_cell_length_b                   10.8500(12)
_cell_length_c                   26.819(4)
_cell_measurement_reflns_used    2754
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.758
_cell_measurement_theta_min      2.9525
_cell_volume                     2184.8(5)
_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  0.115
_diffrn_reflns_av_unetI/netI     0.1720
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            57256
_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         25.680
_diffrn_reflns_theta_min         2.953
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.014
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     104
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1705
_refine_ls_R_factor_gt           0.0744
_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)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2243
_reflns_number_total             4137
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00384a2.cif
_cod_data_source_block           compound6
_cod_depositor_comments
'Adding full bibliography for 7246767--7246772.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7246770
_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   0.404
_shelx_estimated_absorpt_t_max   0.961
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 0.38180(12) 0.41323(9) 0.54093(4) 0.0213(3) Uani 1 1 d . . . . .
Cu2 Cu -0.00922(12) 0.48776(9) 0.63351(3) 0.0215(3) Uani 1 1 d . . . . .
O1 O 0.6281(6) 0.4872(5) 0.54114(19) 0.0235(13) Uani 1 1 d . . . . .
O5 O 0.4146(6) 0.2593(4) 0.50234(18) 0.0207(13) Uani 1 1 d . . . . .
O7 O -0.2149(6) 0.3729(5) 0.64978(19) 0.0213(13) Uani 1 1 d . . . . .
O3 O -0.0010(6) 0.5982(5) 0.69208(19) 0.0254(13) Uani 1 1 d . . . . .
O2 O 0.8060(7) 0.6108(5) 0.58731(19) 0.0277(14) Uani 1 1 d . . . . .
O6 O 0.2795(7) 0.0870(5) 0.47758(19) 0.0271(13) Uani 1 1 d . . . . .
N1 N 0.3540(8) 0.5348(6) 0.5918(2) 0.0209(14) Uani 1 1 d . U . . .
N2 N 0.2232(8) 0.5570(6) 0.6242(2) 0.0211(15) Uani 1 1 d . U . . .
N3 N 0.1568(8) 0.3347(6) 0.5544(2) 0.0194(14) Uani 1 1 d . U . . .
O8 O -0.3531(7) 0.2006(5) 0.6255(2) 0.0380(16) Uani 1 1 d . U . . .
O4 O 0.1775(7) 0.7300(5) 0.7331(2) 0.0374(16) Uani 1 1 d . . . . .
N4 N 0.0259(8) 0.3576(6) 0.5861(2) 0.0220(15) Uani 1 1 d . U . . .
N6 N -0.3898(8) 0.4097(6) 0.9339(2) 0.0284(16) Uani 1 1 d . U . . .
H6 H -0.4885 0.4085 0.9498 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1307(9) 0.2229(7) 0.5332(3) 0.0177(16) Uani 1 1 d . U . . .
C9 C -0.0858(9) 0.2625(7) 0.5851(3) 0.0171(16) Uani 1 1 d . U . . .
C1 C 0.6595(10) 0.5650(7) 0.5766(3) 0.0224(18) Uani 1 1 d . U . . .
N5 N 0.5249(9) 0.3849(7) 0.7148(3) 0.0345(19) Uani 1 1 d . . . . .
H5 H 0.6154 0.3694 0.6965 0.041 Uiso 1 1 calc R U . . .
C8 C -0.0298(9) 0.1737(7) 0.5515(3) 0.0200(17) Uani 1 1 d . U . . .
H8 H -0.0848 0.0996 0.5431 0.024 Uiso 1 1 calc R U . . .
C22 C -0.2664(10) 0.3247(8) 0.9454(3) 0.0278(19) Uani 1 1 d . U . . .
H22 H -0.2862 0.2667 0.9702 0.033 Uiso 1 1 calc R U . . .
C10 C -0.2317(10) 0.2762(8) 0.6213(3) 0.0230(18) Uani 1 1 d . U . . .
C4 C 0.2846(9) 0.6320(7) 0.6599(3) 0.0188(17) Uani 1 1 d . U . . .
C6 C 0.2821(10) 0.1845(7) 0.5010(3) 0.0197(17) Uani 1 1 d . U . . .
C2 C 0.5007(9) 0.5944(7) 0.6080(3) 0.0191(16) Uani 1 1 d . U . . .
C3 C 0.4614(10) 0.6588(7) 0.6508(3) 0.024(2) Uani 1 1 d . . . . .
H3 H 0.5371 0.7091 0.6695 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1457(11) 0.6581(8) 0.6986(3) 0.028(2) Uani 1 1 d . . . . .
C20 C -0.0816(10) 0.4109(8) 0.8832(3) 0.0226(19) Uani 1 1 d . . . . .
C21 C -0.1107(10) 0.3253(7) 0.9196(3) 0.0225(19) Uani 1 1 d . . . . .
H21 H -0.0235 0.2670 0.9270 0.027 Uiso 1 1 calc R U . . .
C18 C -0.3676(11) 0.4942(8) 0.8998(3) 0.031(2) Uani 1 1 d . . . . .
H18 H -0.4556 0.5530 0.8939 0.037 Uiso 1 1 calc R U . . .
C19 C -0.2148(11) 0.4957(8) 0.8730(3) 0.032(2) Uani 1 1 d . . . . .
H19 H -0.2002 0.5537 0.8479 0.038 Uiso 1 1 calc R U . . .
C17 C 0.0938(10) 0.4065(8) 0.8548(3) 0.034(2) Uani 1 1 d . . . . .
H17A H 0.1851 0.4485 0.8743 0.040 Uiso 1 1 calc R U . . .
H17B H 0.1301 0.3212 0.8512 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2428(11) 0.4338(8) 0.7725(3) 0.031(2) Uani 1 1 d . . . . .
C12 C 0.2325(12) 0.3433(8) 0.7366(3) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.1287 0.2975 0.7325 0.049 Uiso 1 1 calc R U . . .
C16 C 0.0809(10) 0.4652(8) 0.8037(3) 0.033(2) Uani 1 1 d . . . . .
H16A H 0.0722 0.5540 0.8073 0.040 Uiso 1 1 calc R U . . .
H16B H -0.0261 0.4365 0.7867 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3758(12) 0.3213(9) 0.7071(3) 0.043(3) Uani 1 1 d . . . . .
H11 H 0.3690 0.2625 0.6819 0.052 Uiso 1 1 calc R U . . .
C15 C 0.5394(11) 0.4713(9) 0.7495(3) 0.038(2) Uani 1 1 d . . . . .
H15 H 0.6461 0.5139 0.7534 0.045 Uiso 1 1 calc R U . . .
C14 C 0.4002(11) 0.4985(9) 0.7797(3) 0.036(2) Uani 1 1 d . . . . .
H14 H 0.4106 0.5586 0.8042 0.043 Uiso 1 1 calc R U . . .
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
N1 Cu1 N3 93.8(3) . . ?
N1 Cu1 O5 165.9(2) . . ?
N3 Cu1 O5 80.9(2) . . ?
N1 Cu1 O1 80.4(2) . . ?
N3 Cu1 O1 168.6(2) . . ?
O5 Cu1 O1 102.5(2) . . ?
N2 Cu2 N4 93.9(3) . . ?
N2 Cu2 O3 81.2(2) . . ?
N4 Cu2 O3 165.7(2) . . ?
N2 Cu2 O7 163.9(2) . . ?
N4 Cu2 O7 78.7(2) . . ?
O3 Cu2 O7 102.5(2) . . ?
N2 Cu2 O2 104.3(2) . 1_455 ?
N4 Cu2 O2 99.2(2) . 1_455 ?
O3 Cu2 O2 95.1(2) . 1_455 ?
O7 Cu2 O2 91.00(19) . 1_455 ?
C1 O1 Cu1 114.9(4) . . ?
C6 O5 Cu1 116.4(5) . . ?
C10 O7 Cu2 115.7(5) . . ?
C5 O3 Cu2 115.5(5) . . ?
C1 O2 Cu2 115.0(5) . 1_655 ?
N2 N1 C2 108.0(6) . . ?
N2 N1 Cu1 132.4(5) . . ?
C2 N1 Cu1 117.7(5) . . ?
C4 N2 N1 109.0(6) . . ?
C4 N2 Cu2 116.9(5) . . ?
N1 N2 Cu2 133.5(5) . . ?
N4 N3 C7 109.3(6) . . ?
N4 N3 Cu1 133.8(5) . . ?
C7 N3 Cu1 116.1(5) . . ?
C9 N4 N3 108.3(6) . . ?
C9 N4 Cu2 119.4(5) . . ?
N3 N4 Cu2 132.0(5) . . ?
C18 N6 C22 123.3(7) . . ?
C18 N6 H6 118.4 . . ?
C22 N6 H6 118.4 . . ?
N3 C7 C8 108.2(6) . . ?
N3 C7 C6 112.7(6) . . ?
C8 C7 C6 138.9(7) . . ?
N4 C9 C8 110.8(6) . . ?
N4 C9 C10 112.4(6) . . ?
C8 C9 C10 136.7(7) . . ?
O2 C1 O1 125.9(7) . . ?
O2 C1 C2 119.6(7) . . ?
O1 C1 C2 114.4(7) . . ?
C15 N5 C11 122.5(8) . . ?
C15 N5 H5 118.8 . . ?
C11 N5 H5 118.8 . . ?
C9 C8 C7 103.3(6) . . ?
C9 C8 H8 128.3 . . ?
C7 C8 H8 128.3 . . ?
N6 C22 C21 118.4(8) . . ?
N6 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
O8 C10 O7 123.1(7) . . ?
O8 C10 C9 123.3(7) . . ?
O7 C10 C9 113.5(7) . . ?
N2 C4 C3 109.0(7) . . ?
N2 C4 C5 111.9(7) . . ?
C3 C4 C5 139.0(7) . . ?
O6 C6 O5 124.3(7) . . ?
O6 C6 C7 121.8(7) . . ?
O5 C6 C7 113.8(7) . . ?
N1 C2 C3 109.1(6) . . ?
N1 C2 C1 111.7(7) . . ?
C3 C2 C1 139.0(7) . . ?
C2 C3 C4 104.9(6) . . ?
C2 C3 H3 127.6 . . ?
C4 C3 H3 127.6 . . ?
O4 C5 O3 125.3(8) . . ?
O4 C5 C4 120.5(8) . . ?
O3 C5 C4 114.2(7) . . ?
C21 C20 C19 118.0(7) . . ?
C21 C20 C17 118.8(7) . . ?
C19 C20 C17 123.2(7) . . ?
C22 C21 C20 120.7(8) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
N6 C18 C19 119.6(8) . . ?
N6 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 120.0(8) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C16 C17 C20 113.1(7) . . ?
C16 C17 H17A 109.0 . . ?
C20 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C20 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C12 C13 C14 119.8(8) . . ?
C12 C13 C16 120.4(8) . . ?
C14 C13 C16 119.8(8) . . ?
C11 C12 C13 119.6(9) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C17 C16 C13 111.2(6) . . ?
C17 C16 H16A 109.4 . . ?
C13 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C13 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N5 C11 C12 119.2(9) . . ?
N5 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N5 C15 C14 121.0(9) . . ?
N5 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C14 C13 117.9(9) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
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 N1 1.912(6) . ?
Cu1 N3 1.931(6) . ?
Cu1 O5 1.982(5) . ?
Cu1 O1 2.016(5) . ?
Cu2 N2 1.920(6) . ?
Cu2 N4 1.922(6) . ?
Cu2 O3 1.976(5) . ?
Cu2 O7 2.037(5) . ?
Cu2 O2 2.279(5) 1_455 ?
O1 C1 1.290(9) . ?
O5 C6 1.284(8) . ?
O7 C10 1.303(9) . ?
O3 C5 1.289(9) . ?
O2 C1 1.237(9) . ?
O2 Cu2 2.279(5) 1_655 ?
O6 C6 1.231(8) . ?
N1 N2 1.343(8) . ?
N1 C2 1.343(9) . ?
N2 C4 1.332(9) . ?
N3 N4 1.332(8) . ?
N3 C7 1.351(9) . ?
O8 C10 1.233(9) . ?
O4 C5 1.229(9) . ?
N4 C9 1.329(9) . ?
N6 C18 1.308(10) . ?
N6 C22 1.340(10) . ?
N6 H6 0.8600 . ?
C7 C8 1.413(9) . ?
C7 C6 1.497(10) . ?
C9 C8 1.388(9) . ?
C9 C10 1.482(10) . ?
C1 C2 1.504(10) . ?
N5 C15 1.325(10) . ?
N5 C11 1.329(10) . ?
N5 H5 0.8600 . ?
C8 H8 0.9300 . ?
C22 C21 1.366(10) . ?
C22 H22 0.9300 . ?
C4 C3 1.384(10) . ?
C4 C5 1.510(11) . ?
C2 C3 1.381(10) . ?
C3 H3 0.9300 . ?
C20 C21 1.369(10) . ?
C20 C19 1.384(11) . ?
C20 C17 1.531(10) . ?
C21 H21 0.9300 . ?
C18 C19 1.363(11) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C17 C16 1.514(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C13 C12 1.377(12) . ?
C13 C14 1.385(12) . ?
C13 C16 1.524(10) . ?
C12 C11 1.366(11) . ?
C12 H12 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C11 H11 0.9300 . ?
C15 C14 1.363(11) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
