#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222069.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_2222069
loop_
_publ_author_name
'Davydenko, Yuliya M.'
'Fritsky, Igor O.'
'Pavlenko, Vadim O.'
'Meyer, Franc'
'Dechert, Sebastian'
_publ_section_title
Bis(acetato-κ²O,O')bis(3,5-dimethyl-1H-pyrazole-κN²)copper(II)
_journal_coeditor_code           HY2196
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m691
_journal_page_last               m692
_journal_paper_doi               10.1107/S1600536809019400
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C2 H3 O2)2 (C5 H8 N2)2]'
_chemical_formula_moiety         'C14 H22 Cu N4 O4'
_chemical_formula_sum            'C14 H22 Cu N4 O4'
_chemical_formula_weight         373.90
_chemical_name_systematic
;
Bis(acetato-κ²O,O')bis(3,5-dimethyl-1H-pyrazole-
κN²)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           SHELXL97
_cell_angle_alpha                110.755(9)
_cell_angle_beta                 100.901(10)
_cell_angle_gamma                99.383(9)
_cell_formula_units_Z            2
_cell_length_a                   9.2861(11)
_cell_length_b                   10.1684(12)
_cell_length_c                   10.3139(13)
_cell_measurement_reflns_used    7882
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.19
_cell_volume                     865.7(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Stoe IPDSII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7882
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    1.285
_exptl_absorpt_correction_T_max  0.9354
_exptl_absorpt_correction_T_min  0.7897
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.657
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0315
_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)+(0.0405P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0714
_reflns_number_gt                3129
_reflns_number_total             3713
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2196.cif
_cod_data_source_block           I
_cod_database_code               2222069
_cod_database_fobs_code          2222069
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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.59542(3) 0.26364(3) 0.28774(3) 0.01892(8) Uani d . 1 . .
N N1 0.46111(18) 0.31000(19) 0.1448(2) 0.0219(4) Uani d . 1 . .
N N2 0.35711(19) 0.2059(2) 0.0274(2) 0.0236(4) Uani d . 1 . .
N N3 0.41420(18) 0.17191(19) 0.3311(2) 0.0206(4) Uani d . 1 . .
N N4 0.30556(18) 0.2416(2) 0.3681(2) 0.0208(4) Uani d . 1 . .
O O1 0.73397(15) 0.25272(16) 0.45427(17) 0.0241(3) Uani d . 1 . .
O O2 0.69120(17) 0.47040(17) 0.52556(18) 0.0290(3) Uani d . 1 . .
O O3 0.77354(16) 0.32001(17) 0.21787(18) 0.0274(3) Uani d . 1 . .
O O4 0.67255(17) 0.08587(17) 0.09809(18) 0.0313(4) Uani d . 1 . .
C C1 0.4435(2) 0.4379(2) 0.1444(2) 0.0236(4) Uani d . 1 . .
C C2 0.3264(2) 0.4129(3) 0.0235(3) 0.0281(5) Uani d . 1 . .
H H2A 0.2906 0.4827 -0.0025 0.080 Uiso calc R 1 . .
C C3 0.2751(2) 0.2644(3) -0.0486(2) 0.0264(5) Uani d . 1 . .
C C4 0.5404(3) 0.5761(2) 0.2603(3) 0.0295(5) Uani d . 1 . .
H H4A 0.4975 0.6013 0.3409 0.080 Uiso calc R 1 . .
H H4B 0.5460 0.6519 0.2251 0.080 Uiso calc R 1 . .
H H4C 0.6402 0.5645 0.2900 0.080 Uiso calc R 1 . .
C C5 0.1575(3) 0.1717(3) -0.1863(3) 0.0361(6) Uani d . 1 . .
H H5A 0.2058 0.1261 -0.2587 0.080 Uiso calc R 1 . .
H H5B 0.1002 0.2310 -0.2170 0.080 Uiso calc R 1 . .
H H5C 0.0909 0.0986 -0.1719 0.080 Uiso calc R 1 . .
C C6 0.3738(2) 0.0426(2) 0.3370(2) 0.0223(4) Uani d . 1 . .
C C7 0.2394(2) 0.0308(2) 0.3797(3) 0.0260(5) Uani d . 1 . .
H H7 0.1875 -0.0481 0.3924 0.080 Uiso calc R 1 . .
C C8 0.1996(2) 0.1597(2) 0.3991(2) 0.0226(4) Uani d . 1 . .
C C9 0.4646(3) -0.0668(3) 0.2981(3) 0.0331(5) Uani d . 1 . .
H H9A 0.4376 -0.1180 0.1954 0.080 Uiso calc R 1 . .
H H9B 0.4442 -0.1345 0.3417 0.080 Uiso calc R 1 . .
H H9C 0.5705 -0.0183 0.3320 0.080 Uiso calc R 1 . .
C C10 0.0700(2) 0.2149(3) 0.4456(3) 0.0317(5) Uani d . 1 . .
H H10A 0.1082 0.3080 0.5246 0.080 Uiso calc R 1 . .
H H10B 0.0138 0.1479 0.4753 0.080 Uiso calc R 1 . .
H H10C 0.0049 0.2240 0.3668 0.080 Uiso calc R 1 . .
C C11 0.7570(2) 0.3795(2) 0.5494(2) 0.0232(4) Uani d . 1 . .
C C12 0.8678(3) 0.4198(3) 0.6921(3) 0.0344(5) Uani d . 1 . .
H H12A 0.9637 0.4742 0.6944 0.080 Uiso calc R 1 . .
H H12B 0.8803 0.3331 0.7054 0.080 Uiso calc R 1 . .
H H12C 0.8303 0.4777 0.7678 0.080 Uiso calc R 1 . .
C C13 0.7706(2) 0.1986(3) 0.1243(2) 0.0268(5) Uani d . 1 . .
C C14 0.8912(3) 0.1923(3) 0.0435(3) 0.0450(7) Uani d . 1 . .
H H14A 0.9847 0.1944 0.1038 0.080 Uiso calc R 1 . .
H H14B 0.9053 0.2743 0.0174 0.080 Uiso calc R 1 . .
H H14C 0.8601 0.1042 -0.0418 0.080 Uiso calc R 1 . .
H H4 0.319(3) 0.334(3) 0.384(3) 0.023(6) Uiso d . 1 . .
H H2 0.351(3) 0.118(3) 0.003(3) 0.027(7) 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 O1 . . 170.00(7) ?
N1 Cu1 N3 . . 89.80(7) ?
O1 Cu1 N3 . . 91.52(7) ?
N1 Cu1 O3 . . 90.43(7) ?
O1 Cu1 O3 . . 90.04(6) ?
N3 Cu1 O3 . . 169.70(7) ?
N1 Cu1 O4 . . 91.91(7) ?
O1 Cu1 O4 . . 96.79(6) ?
N3 Cu1 O4 . . 111.84(6) ?
O3 Cu1 O4 . . 57.86(6) ?
N1 Cu1 O2 . . 112.23(6) ?
O1 Cu1 O2 . . 57.78(6) ?
N3 Cu1 O2 . . 95.42(7) ?
O3 Cu1 O2 . . 94.03(6) ?
O4 Cu1 O2 . . 143.81(5) ?
C1 N1 N2 . . 106.62(17) ?
C1 N1 Cu1 . . 130.74(16) ?
N2 N1 Cu1 . . 122.49(13) ?
C3 N2 N1 . . 111.34(19) ?
C3 N2 H2 . . 125.2(19) ?
N1 N2 H2 . . 123.2(18) ?
C6 N3 N4 . . 106.06(15) ?
C6 N3 Cu1 . . 131.10(13) ?
N4 N3 Cu1 . . 122.80(13) ?
C8 N4 N3 . . 111.35(17) ?
C8 N4 H4 . . 127.8(15) ?
N3 N4 H4 . . 119.9(15) ?
C11 O1 Cu1 . . 101.34(13) ?
C11 O2 Cu1 . . 79.30(13) ?
C13 O3 Cu1 . . 100.41(13) ?
C13 O4 Cu1 . . 79.78(13) ?
N1 C1 C2 . . 109.0(2) ?
N1 C1 C4 . . 120.58(19) ?
C2 C1 C4 . . 130.46(19) ?
C3 C2 C1 . . 106.30(19) ?
C3 C2 H2A . . 126.8 ?
C1 C2 H2A . . 126.8 ?
N2 C3 C2 . . 106.8(2) ?
N2 C3 C5 . . 121.5(2) ?
C2 C3 C5 . . 131.7(2) ?
C1 C4 H4A . . 109.5 ?
C1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N3 C6 C7 . . 109.75(17) ?
N3 C6 C9 . . 121.28(18) ?
C7 C6 C9 . . 128.9(2) ?
C8 C7 C6 . . 106.03(18) ?
C8 C7 H7 . . 127.0 ?
C6 C7 H7 . . 127.0 ?
N4 C8 C7 . . 106.80(17) ?
N4 C8 C10 . . 121.04(19) ?
C7 C8 C10 . . 132.2(2) ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O2 C11 O1 . . 121.5(2) ?
O2 C11 C12 . . 120.4(2) ?
O1 C11 C12 . . 118.11(19) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O4 C13 O3 . . 121.95(19) ?
O4 C13 C14 . . 120.2(2) ?
O3 C13 C14 . . 117.8(2) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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 N1 . 1.9851(18) y
Cu1 N3 . 1.9925(16) y
Cu1 O1 . 1.9909(15) y
Cu1 O2 . 2.4774(18) y
Cu1 O3 . 2.0045(14) y
Cu1 O4 . 2.4603(16) y
N1 C1 . 1.338(3) ?
N1 N2 . 1.355(3) ?
N2 C3 . 1.342(3) ?
N2 H2 . 0.82(3) ?
N3 C6 . 1.333(3) ?
N3 N4 . 1.361(2) ?
N4 C8 . 1.343(3) ?
N4 H4 . 0.87(3) ?
O1 C11 . 1.266(3) ?
O2 C11 . 1.256(2) ?
O3 C13 . 1.262(3) ?
O4 C13 . 1.250(3) ?
C1 C2 . 1.405(3) ?
C1 C4 . 1.485(3) ?
C2 C3 . 1.377(3) ?
C2 H2A . 0.9300 ?
C3 C5 . 1.492(3) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C7 . 1.402(3) ?
C6 C9 . 1.492(3) ?
C7 C8 . 1.377(3) ?
C7 H7 . 0.9300 ?
C8 C10 . 1.497(3) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.502(3) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.513(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
N2 H2 O4 2_655 0.82(3) 1.92(3) 2.726(3) 166(3) y
N4 H4 O2 2_666 0.87(3) 1.91(3) 2.732(2) 157(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139076653
