#------------------------------------------------------------------------------
#$Date: 2025-03-04 22:23:36 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/77/7717701.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_7717701
loop_
_publ_author_name
'Hsieh, Chang-Chih'
'Chen, Chia-Wei'
'Chiang, Ming-Hsi'
'Horng, Yih-Chern'
_publ_section_title
;
 Cu(II)-mediated tautomerization for the pyrazole-nitrile coupling
 reaction.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1334
_journal_page_last               1342
_journal_paper_doi               10.1039/d4dt02904f
_journal_volume                  54
_journal_year                    2025
_chemical_formula_sum            'C16 H24 Cl2 Cu N8 O8'
_chemical_formula_weight         590.88
_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
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-12-04 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.491(4)
_cell_angle_beta                 117.756(4)
_cell_angle_gamma                110.978(4)
_cell_formula_units_Z            1
_cell_length_a                   8.8912(5)
_cell_length_b                   8.8939(6)
_cell_length_c                   9.1265(6)
_cell_measurement_reflns_used    2767
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.58
_cell_volume                     582.75(7)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker AXS, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.581
_exptl_absorpt_coefficient_mu    1.227
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            blue-purple
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.984
_refine_diff_density_min         -1.182
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0418
_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)+(0.1000P)²+0.1526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2359
_reflns_number_total             2880
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02904f2.cif
_cod_data_source_block           2d
_cod_depositor_comments
'Adding full bibliography for 7717689--7717702.cif.'
_cod_database_code               7717701
_shelx_shelxl_version_number     2019/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.500000 1.000000 0.500000 0.01687(15) Uani 1 2 d S . P . .
Cl1 Cl 0.67744(9) 0.70069(7) 0.70773(8) 0.02321(17) Uani 1 1 d . . . . .
N1 N 0.4042(3) 0.8974(3) 0.2605(3) 0.0190(4) Uani 1 1 d . . . . .
N2 N 0.3314(3) 0.7323(3) 0.2034(3) 0.0200(4) Uani 1 1 d . . . . .
H3 H 0.333362 0.660050 0.268717 0.024 Uiso 1 1 calc R U . . .
O4 O 0.7198(3) 0.5734(2) 0.6599(3) 0.0305(5) Uani 1 1 d . . . . .
O2 O 0.8474(3) 0.8347(3) 0.8329(3) 0.0340(5) Uani 1 1 d . . . . .
O1 O 0.5884(3) 0.7652(2) 0.5603(2) 0.0285(4) Uani 1 1 d . . . . .
O3 O 0.5554(3) 0.6352(3) 0.7747(3) 0.0334(5) Uani 1 1 d . . . . .
C3 C 0.2556(4) 0.6927(3) 0.0339(3) 0.0227(5) Uani 1 1 d . . . . .
C6 C -0.0029(4) 0.7077(3) 0.4825(3) 0.0246(5) Uani 1 1 d . . . . .
H6 H -0.079133 0.629016 0.516199 0.029 Uiso 1 1 calc R U . . .
C7 C -0.0561(4) 0.8012(3) 0.3641(3) 0.0217(5) Uani 1 1 d . . . . .
N4 N 0.0965(3) 0.8946(3) 0.3575(3) 0.0211(4) Uani 1 1 d . . . . .
H7 H 0.098231 0.964856 0.290318 0.025 Uiso 1 1 calc R U . . .
C1 C 0.3714(4) 0.9611(3) 0.1239(3) 0.0246(5) Uani 1 1 d . . . . .
H1 H 0.406412 1.075434 0.124739 0.030 Uiso 1 1 calc R U . . .
C2 C 0.2791(4) 0.8389(4) -0.0208(3) 0.0275(6) Uani 1 1 d . . . . .
H2 H 0.240219 0.853119 -0.133971 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1720(4) 0.5210(4) -0.0621(4) 0.0330(7) Uani 1 1 d . . . . .
H4A H 0.120182 0.444308 -0.004575 0.050 Uiso 1 1 calc R U . . .
H4B H 0.268140 0.496202 -0.068150 0.050 Uiso 1 1 calc R U . . .
H4C H 0.072637 0.509331 -0.177021 0.050 Uiso 1 1 calc R U . . .
N3 N 0.2470(3) 0.8679(3) 0.4662(3) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.1865(4) 0.7532(3) 0.5422(3) 0.0230(5) Uani 1 1 d . . . . .
H5 H 0.261717 0.708659 0.625447 0.028 Uiso 1 1 calc R U . . .
C8 C -0.2407(4) 0.8067(4) 0.2551(4) 0.0340(7) Uani 1 1 d . . . . .
H8A H -0.256156 0.821965 0.143510 0.051 Uiso 1 1 calc R U . . .
H8B H -0.247274 0.898736 0.308059 0.051 Uiso 1 1 calc R U . . .
H8C H -0.339855 0.703129 0.242264 0.051 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'
Cl Cl 0.1484 0.1585 '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 N3 180.0 . 2_676 ?
N3 Cu1 N1 88.08(9) . . ?
N3 Cu1 N1 91.92(9) 2_676 . ?
N3 Cu1 N1 91.92(9) . 2_676 ?
N3 Cu1 N1 88.08(9) 2_676 2_676 ?
N1 Cu1 N1 180.0 . 2_676 ?
N3 Cu1 O1 91.70(8) . . ?
N3 Cu1 O1 88.30(8) 2_676 . ?
N1 Cu1 O1 82.59(8) . . ?
N1 Cu1 O1 97.41(8) 2_676 . ?
O3 Cl1 O4 109.85(13) . . ?
O3 Cl1 O2 110.05(14) . . ?
O4 Cl1 O2 109.83(13) . . ?
O3 Cl1 O1 109.76(13) . . ?
O4 Cl1 O1 109.41(12) . . ?
O2 Cl1 O1 107.91(12) . . ?
C1 N1 N2 105.3(2) . . ?
C1 N1 Cu1 131.17(18) . . ?
N2 N1 Cu1 122.89(16) . . ?
C3 N2 N1 111.6(2) . . ?
C3 N2 H3 124.2 . . ?
N1 N2 H3 124.2 . . ?
Cl1 O1 Cu1 137.58(12) . . ?
N2 C3 C2 106.3(2) . . ?
N2 C3 C4 123.3(3) . . ?
C2 C3 C4 130.4(3) . . ?
C7 C6 C5 105.5(2) . . ?
C7 C6 H6 127.2 . . ?
C5 C6 H6 127.2 . . ?
N4 C7 C6 106.6(2) . . ?
N4 C7 C8 122.4(3) . . ?
C6 C7 C8 131.0(3) . . ?
C7 N4 N3 112.0(2) . . ?
C7 N4 H7 124.0 . . ?
N3 N4 H7 124.0 . . ?
N1 C1 C2 111.2(2) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
C3 C2 C1 105.6(2) . . ?
C3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 N3 N4 105.4(2) . . ?
C5 N3 Cu1 132.53(18) . . ?
N4 N3 Cu1 121.85(16) . . ?
N3 C5 C6 110.5(2) . . ?
N3 C5 H5 124.8 . . ?
C6 C5 H5 124.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 1.997(2) . ?
Cu1 N3 1.997(2) 2_676 ?
Cu1 N1 2.002(2) . ?
Cu1 N1 2.002(2) 2_676 ?
Cu1 O1 2.4647(18) . ?
Cl1 O3 1.436(2) . ?
Cl1 O4 1.437(2) . ?
Cl1 O2 1.445(2) . ?
Cl1 O1 1.4536(19) . ?
N1 C1 1.324(3) . ?
N1 N2 1.356(3) . ?
N2 C3 1.349(3) . ?
N2 H3 0.8800 . ?
C3 C2 1.378(4) . ?
C3 C4 1.486(4) . ?
C6 C7 1.379(4) . ?
C6 C5 1.397(4) . ?
C6 H6 0.9500 . ?
C7 N4 1.343(4) . ?
C7 C8 1.491(4) . ?
N4 N3 1.352(3) . ?
N4 H7 0.8800 . ?
C1 C2 1.388(4) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N3 C5 1.334(3) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 0.6(3) . . . . ?
Cu1 N1 N2 C3 172.26(17) . . . . ?
O3 Cl1 O1 Cu1 70.2(2) . . . . ?
O4 Cl1 O1 Cu1 -169.23(16) . . . . ?
O2 Cl1 O1 Cu1 -49.8(2) . . . . ?
N1 N2 C3 C2 -0.6(3) . . . . ?
N1 N2 C3 C4 177.7(2) . . . . ?
C5 C6 C7 N4 0.1(3) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
C6 C7 N4 N3 -0.4(3) . . . . ?
C8 C7 N4 N3 -179.4(2) . . . . ?
N2 N1 C1 C2 -0.3(3) . . . . ?
Cu1 N1 C1 C2 -171.04(19) . . . . ?
N2 C3 C2 C1 0.4(3) . . . . ?
C4 C3 C2 C1 -177.7(3) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
C7 N4 N3 C5 0.5(3) . . . . ?
C7 N4 N3 Cu1 -175.17(16) . . . . ?
N4 N3 C5 C6 -0.4(3) . . . . ?
Cu1 N3 C5 C6 174.60(18) . . . . ?
C7 C6 C5 N3 0.2(3) . . . . ?
