#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/68/2006831.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_2006831
loop_
_publ_author_name
'Warda, Salam A.'
_publ_section_title
Bis(3,5-dimethylpyrazole-N²)(N-salicylideneglycinato-O,N,O')copper(II)
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1759
_journal_page_last               1761
_journal_paper_doi               10.1107/S0108270197009104
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          '[Cu (C9 H7 O3 N) (C5 H8 N2)2]'
_chemical_formula_sum            'C19 H23 Cu N5 O3'
_chemical_formula_weight         432.96
_chemical_name_systematic
;
 Bis(3,5-dimethylpyrazole)(N-salicylideneglycinato)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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.046(14)
_cell_angle_beta                 93.663(15)
_cell_angle_gamma                99.182(16)
_cell_formula_units_Z            2
_cell_length_a                   8.9206(19)
_cell_length_b                   10.484(2)
_cell_length_c                   10.8614(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.07
_cell_measurement_theta_min      34.47
_cell_volume                     998.7(3)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS (Enraf Nonius, 1992)'
_computing_data_reduction        'XCAD4 (Harms, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Siemens, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS96 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0093
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3128
_diffrn_reflns_theta_full        59.95
_diffrn_reflns_theta_max         59.95
_diffrn_reflns_theta_min         4.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.796
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Dark green'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             450
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.577
_refine_ls_extinction_coef       0.0050(7)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0442
_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)+(0.0753P)²+1.1666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2901
_reflns_number_total             2950
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jz1209.cif
_cod_data_source_block           saa35ohne
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0753P)^2^+1.1666P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0753P)^2^+1.1666P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2006831
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Cu .68628(5) .30219(4) .22100(4) .0349(2) Uani d . 1 . . Cu
O1 .7592(3) .1928(2) .3381(2) .0519(6) Uani d . 1 . . O
N1 .7119(3) .4479(3) .3437(2) .0432(7) Uani d . 1 . . N
C1 .8156(4) .2251(4) .4516(3) .0439(8) Uani d . 1 . . C
O2 .6684(3) .4416(2) .10425(18) .0384(5) Uani d . 1 . . O
N2 .6904(3) .1784(3) .0741(2) .0373(6) Uani d . 1 . . N
C2 .8740(5) .1294(4) .5190(4) .0589(10) Uani d . 1 . . C
H2 .8727 .0477 .4807 .071 Uiso calc R 1 . . H
O3 .6184(3) .6425(2) .0996(2) .0490(6) Uani d . 1 . . O
N3 .6140(3) .2037(3) -.0318(2) .0393(6) Uani d . 1 . . N
H31 .5768 .2794 -.0373 .047 Uiso d R 1 . . H
C3 .9319(5) .1543(5) .6382(4) .0738(13) Uani d . 1 . . C
H3 .9679 .0889 .6801 .089 Uiso calc R 1 . . H
N4 .4226(3) .2793(3) .2351(2) .0411(6) Uani d . 1 . . N
C4 .9383(6) .2744(6) .6982(4) .0880(16) Uani d . 1 . . C
H4 .9780 .2899 .7798 .106 Uiso calc R 1 . . H
N5 .3314(3) .3233(3) .1483(2) .0416(6) Uani d . 1 . . N
H51 .3586 .3452 .0686 .050 Uiso d R 1 . . H
C5 .8856(6) .3703(5) .6364(4) .0763(14) Uani d . 1 . . C
H5 .8906 .4517 .6764 .092 Uiso calc R 1 . . H
C6 .8233(4) .3480(4) .5123(3) .0503(9) Uani d . 1 . . C
C7 .7693(5) .4530(4) .4546(3) .0532(9) Uani d . 1 . . C
H7 .7766 .5309 .5016 .064 Uiso calc R 1 . . H
C8 .6564(5) .5603(3) .2950(3) .0530(9) Uani d . 1 . . C
H8A .7247 .6388 .3251 .064 Uiso calc R 1 . . H
H8B .5564 .5655 .3232 .064 Uiso calc R 1 . . H
C9 .6473(4) .5482(3) .1546(3) .0371(7) Uani d . 1 . . C
C10 .6168(4) .1145(3) -.1232(3) .0434(8) Uani d . 1 . . C
C11 .6995(4) .0266(3) -.0761(3) .0473(8) Uani d . 1 . . C
H11 .7221 -.0469 -.1179 .057 Uiso calc R 1 . . H
C12 .7428(4) .0683(3) .0459(3) .0405(7) Uani d . 1 . . C
C13 .8371(5) .0061(4) .1356(4) .0566(10) Uani d . 1 . . C
H13A .8039 .0184 .2171 .085 Uiso calc R 1 . . H
H13B .9420 .0447 .1346 .085 Uiso calc R 1 . . H
H13C .8261 -.0848 .1129 .085 Uiso calc R 1 . . H
C14 .5403(5) .1206(4) -.2483(3) .0623(11) Uani d . 1 . . C
H14A .4736 .1839 -.2450 .094 Uiso calc R 1 . . H
H14B .4823 .0374 -.2746 .094 Uiso calc R 1 . . H
H14C .6157 .1446 -.3058 .094 Uiso calc R 1 . . H
C15 .1872(4) .3136(4) .1788(4) .0494(9) Uani d . 1 . . C
C16 .1838(4) .2625(4) .2914(4) .0554(10) Uani d . 1 . . C
H16 .0994 .2439 .3373 .067 Uiso calc R 1 . . H
C17 .3326(4) .2434(3) .3244(3) .0440(8) Uani d . 1 . . C
C18 .3930(5) .1915(4) .4386(3) .0604(10) Uani d . 1 . . C
H18A .4646 .1360 .4178 .091 Uiso calc R 1 . . H
H18B .3105 .1430 .4776 .091 Uiso calc R 1 . . H
H18C .4427 .2620 .4942 .091 Uiso calc R 1 . . H
C19 .0700(5) .3564(6) .0932(5) .0763(13) Uani d . 1 . . C
H19A .1177 .4246 .0462 .115 Uiso calc R 1 . . H
H19B -.0058 .3874 .1402 .115 Uiso calc R 1 . . H
H19C .0228 .2846 .0379 .115 Uiso calc R 1 . . H
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'
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
_geom_angle_publ_flag
O1 Cu N1 91.86(11) y
O1 Cu O2 164.41(11) y
N1 Cu O2 82.28(10) y
O1 Cu N2 94.82(10) y
N1 Cu N2 167.52(12) y
O2 Cu N2 88.55(9) y
O1 Cu N4 106.30(11) y
N1 Cu N4 88.96(11) y
O2 Cu N4 88.10(9) y
N2 Cu N4 99.22(10) y
C1 O1 Cu 127.6(2) ?
C7 N1 C8 120.3(3) ?
C7 N1 Cu 127.6(3) ?
C8 N1 Cu 112.1(2) ?
O1 C1 C6 125.0(3) ?
O1 C1 C2 117.8(3) ?
C6 C1 C2 117.2(3) ?
C9 O2 Cu 114.87(19) ?
C12 N2 N3 104.7(2) ?
C12 N2 Cu 139.1(2) ?
N3 N2 Cu 116.08(19) ?
C3 C2 C1 121.6(4) ?
C3 C2 H2 119.2 ?
C1 C2 H2 119.2 ?
C10 N3 N2 112.4(3) ?
C10 N3 H31 126.8 ?
N2 N3 H31 120.4 ?
C2 C3 C4 121.3(4) ?
C2 C3 H3 119.3 ?
C4 C3 H3 119.3 ?
C17 N4 N5 105.0(3) ?
C17 N4 Cu 133.0(2) ?
N5 N4 Cu 121.4(2) ?
C5 C4 C3 119.2(4) ?
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
C15 N5 N4 112.5(3) ?
C15 N5 H51 121.4 ?
N4 N5 H51 125.3 ?
C4 C5 C6 121.1(5) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C1 C6 C5 119.6(4) ?
C1 C6 C7 122.7(3) ?
C5 C6 C7 117.7(4) ?
N1 C7 C6 124.8(3) ?
N1 C7 H7 117.6 ?
C6 C7 H7 117.6 ?
N1 C8 C9 109.6(3) ?
N1 C8 H8A 109.8 ?
C9 C8 H8A 109.8 ?
N1 C8 H8B 109.8 ?
C9 C8 H8B 109.8 ?
H8A C8 H8B 108.2 ?
O3 C9 O2 125.7(3) ?
O3 C9 C8 117.4(3) ?
O2 C9 C8 117.0(3) ?
N3 C10 C11 106.2(3) ?
N3 C10 C14 122.4(3) ?
C11 C10 C14 131.4(3) ?
C10 C11 C12 106.7(3) ?
C10 C11 H11 126.7 ?
C12 C11 H11 126.7 ?
N2 C12 C11 110.0(3) ?
N2 C12 C13 123.0(3) ?
C11 C12 C13 127.0(3) ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C10 C14 H14A 109.5 ?
C10 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C10 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N5 C15 C16 106.2(3) ?
N5 C15 C19 119.9(4) ?
C16 C15 C19 133.9(4) ?
C15 C16 C17 106.4(3) ?
C15 C16 H16 126.8 ?
C17 C16 H16 126.8 ?
N4 C17 C16 109.9(3) ?
N4 C17 C18 121.2(3) ?
C16 C17 C18 128.9(3) ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C15 C19 H19A 109.5 ?
C15 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C15 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 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
Cu O1 . 1.909(2) y
Cu N1 . 1.948(3) y
Cu O2 . 2.004(2) y
Cu N2 . 2.009(3) y
Cu N4 . 2.342(3) y
O1 C1 . 1.307(4) ?
N1 C7 . 1.274(4) ?
N1 C8 . 1.460(4) ?
C1 C6 . 1.405(5) ?
C1 C2 . 1.418(5) ?
O2 C9 . 1.264(4) ?
N2 C12 . 1.341(4) ?
N2 N3 . 1.359(4) ?
C2 C3 . 1.358(6) ?
C2 H2 . .9300 ?
O3 C9 . 1.235(4) ?
N3 C10 . 1.331(4) ?
N3 H31 . .9116 ?
C3 C4 . 1.378(8) ?
C3 H3 . .9300 ?
N4 C17 . 1.330(4) ?
N4 N5 . 1.354(4) ?
C4 C5 . 1.366(7) ?
C4 H4 . .9300 ?
N5 C15 . 1.338(4) ?
N5 H51 . .9440 ?
C5 C6 . 1.417(5) ?
C5 H5 . .9300 ?
C6 C7 . 1.429(5) ?
C7 H7 . .9300 ?
C8 C9 . 1.519(4) ?
C8 H8A . .9700 ?
C8 H8B . .9700 ?
C10 C11 . 1.369(5) ?
C10 C14 . 1.490(5) ?
C11 C12 . 1.384(5) ?
C11 H11 . .9300 ?
C12 C13 . 1.490(5) ?
C13 H13A . .9600 ?
C13 H13B . .9600 ?
C13 H13C . .9600 ?
C14 H14A . .9600 ?
C14 H14B . .9600 ?
C14 H14C . .9600 ?
C15 C16 . 1.361(6) ?
C15 C19 . 1.494(6) ?
C16 C17 . 1.401(5) ?
C16 H16 . .9300 ?
C17 C18 . 1.485(5) ?
C18 H18A . .9600 ?
C18 H18B . .9600 ?
C18 H18C . .9600 ?
C19 H19A . .9600 ?
C19 H19B . .9600 ?
C19 H19C . .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
N3 H31 O3 2_665 0.91 2.13 2.905(4) 142.7 yes
N5 H51 O3 2_665 0.94 1.86 2.790(4) 167.7 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
N1 Cu O1 C1 -5.8(3)
O2 Cu O1 C1 61.7(5)
N2 Cu O1 C1 163.7(3)
N4 Cu O1 C1 -95.2(3)
O1 Cu N1 C7 4.4(4)
O2 Cu N1 C7 -161.1(4)
N2 Cu N1 C7 -118.0(5)
N4 Cu N1 C7 110.7(3)
O1 Cu N1 C8 -175.7(3)
O2 Cu N1 C8 18.8(3)
N2 Cu N1 C8 61.8(6)
N4 Cu N1 C8 -69.5(3)
Cu O1 C1 C6 4.7(5)
Cu O1 C1 C2 -175.1(3)
O1 Cu O2 C9 -83.2(4)
N1 Cu O2 C9 -14.5(2)
N2 Cu O2 C9 173.9(2)
N4 Cu O2 C9 74.7(2)
O1 Cu N2 C12 -10.5(4)
N1 Cu N2 C12 111.7(5)
O2 Cu N2 C12 154.2(4)
N4 Cu N2 C12 -117.9(4)
O1 Cu N2 N3 165.8(2)
N1 Cu N2 N3 -72.0(5)
O2 Cu N2 N3 -29.4(2)
N4 Cu N2 N3 58.4(2)
O1 C1 C2 C3 -178.7(4)
C6 C1 C2 C3 1.5(6)
C12 N2 N3 C10 0.2(4)
Cu N2 N3 C10 -177.4(2)
C1 C2 C3 C4 -1.0(7)
O1 Cu N4 C17 23.7(3)
N1 Cu N4 C17 -67.9(3)
O2 Cu N4 C17 -150.2(3)
N2 Cu N4 C17 121.6(3)
O1 Cu N4 N5 -166.7(2)
N1 Cu N4 N5 101.6(2)
O2 Cu N4 N5 19.3(2)
N2 Cu N4 N5 -68.9(2)
C2 C3 C4 C5 -0.1(8)
C17 N4 N5 C15 -1.4(4)
Cu N4 N5 C15 -173.5(2)
C3 C4 C5 C6 0.6(9)
O1 C1 C6 C5 179.2(4)
C2 C1 C6 C5 -1.0(6)
O1 C1 C6 C7 -0.2(6)
C2 C1 C6 C7 179.6(4)
C4 C5 C6 C1 0.0(7)
C4 C5 C6 C7 179.4(5)
C8 N1 C7 C6 178.3(4)
Cu N1 C7 C6 -1.9(6)
C1 C6 C7 N1 -1.3(6)
C5 C6 C7 N1 179.3(4)
C7 N1 C8 C9 159.9(3)
Cu N1 C8 C9 -19.9(4)
Cu O2 C9 O3 -172.5(3)
Cu O2 C9 C8 6.7(4)
N1 C8 C9 O3 -172.1(3)
N1 C8 C9 O2 8.7(5)
N2 N3 C10 C11 -0.4(4)
N2 N3 C10 C14 179.7(3)
N3 C10 C11 C12 0.4(4)
C14 C10 C11 C12 -179.6(4)
N3 N2 C12 C11 0.1(4)
Cu N2 C12 C11 176.7(3)
N3 N2 C12 C13 178.7(3)
Cu N2 C12 C13 -4.7(6)
C10 C11 C12 N2 -0.4(4)
C10 C11 C12 C13 -178.8(4)
N4 N5 C15 C16 0.8(4)
N4 N5 C15 C19 -179.4(3)
N5 C15 C16 C17 0.1(4)
C19 C15 C16 C17 -179.7(4)
N5 N4 C17 C16 1.4(4)
Cu N4 C17 C16 172.1(2)
N5 N4 C17 C18 -178.8(3)
Cu N4 C17 C18 -8.0(5)
C15 C16 C17 N4 -1.0(4)
C15 C16 C17 C18 179.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139055818
