#------------------------------------------------------------------------------
#$Date: 2025-03-04 22:23:36 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/76/7717699.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_7717699
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            'C10 H12 Cl4 Cu N6 O8'
_chemical_formula_weight         549.61
_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                81.900(3)
_cell_angle_beta                 74.576(3)
_cell_angle_gamma                74.932(3)
_cell_formula_units_Z            1
_cell_length_a                   6.5992(3)
_cell_length_b                   8.3622(4)
_cell_length_c                   9.3885(5)
_cell_measurement_reflns_used    2769
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      2.26
_cell_volume                     480.83(4)
_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 0.978
_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  0.0219
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6162
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.760
_diffrn_reflns_theta_min         2.257
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       block
_exptl_crystal_F_000             293
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0345
_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)+(0.0455P)²+0.3916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0898
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2131
_reflns_number_total             2450
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02904f2.cif
_cod_data_source_block           1a'
_cod_depositor_comments
'Adding full bibliography for 7717689--7717702.cif.'
_cod_database_code               7717699
_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
O1 O 0.6956(3) 0.7213(2) 0.83720(19) 0.0306(4) Uani 1 1 d . . . . .
N3 N 0.4347(3) 0.4410(2) 0.8241(2) 0.0230(4) Uani 1 1 d . . . . .
H3 H 0.311045 0.481440 0.803467 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 1.32537(9) 0.01890(8) 0.84343(8) 0.03568(17) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 1.000000 0.02158(12) Uani 1 2 d S . P . .
Cl2 Cl 0.84678(8) 0.70345(6) 0.69405(6) 0.02138(13) Uani 1 1 d . . . . .
N1 N 0.7694(3) 0.3333(2) 0.9270(2) 0.0225(4) Uani 1 1 d . . . . .
O2 O 1.0500(3) 0.6064(4) 0.7153(2) 0.0667(8) Uani 1 1 d . . . . .
O4 O 0.7757(4) 0.6185(3) 0.6030(2) 0.0532(6) Uani 1 1 d . . . . .
O3 O 0.8673(4) 0.8616(3) 0.6231(2) 0.0574(7) Uani 1 1 d . . . . .
N2 N 0.7681(3) 0.2763(2) 0.7982(2) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.5864(4) 0.2876(3) 0.5980(3) 0.0299(5) Uani 1 1 d . . . . .
H5A H 0.445527 0.327329 0.578468 0.045 Uiso 1 1 calc R U . . .
H5B H 0.626105 0.168525 0.600555 0.045 Uiso 1 1 calc R U . . .
H5C H 0.689759 0.332532 0.521195 0.045 Uiso 1 1 calc R U . . .
C2 C 1.0773(4) 0.1499(3) 0.8462(3) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.9557(4) 0.1647(3) 0.7470(3) 0.0266(5) Uani 1 1 d . . . . .
H3A H 0.993294 0.109449 0.661066 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5832(4) 0.3407(3) 0.7428(2) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.9563(4) 0.2580(3) 0.9566(3) 0.0254(5) Uani 1 1 d . . . . .
H1 H 1.001707 0.273809 1.038121 0.030 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
Cl2 O1 Cu1 127.71(10) . . ?
C4 N3 Cu1 116.86(16) . . ?
C4 N3 H3 121.6 . . ?
Cu1 N3 H3 121.6 . . ?
N3 Cu1 N3 180.0 . 2_667 ?
N3 Cu1 N1 99.64(8) . 2_667 ?
N3 Cu1 N1 80.36(8) 2_667 2_667 ?
N3 Cu1 N1 80.36(8) . . ?
N3 Cu1 N1 99.64(8) 2_667 . ?
N1 Cu1 N1 180.0 2_667 . ?
N3 Cu1 O1 90.39(7) . . ?
N3 Cu1 O1 89.61(7) 2_667 . ?
N1 Cu1 O1 93.49(7) 2_667 . ?
N1 Cu1 O1 86.51(7) . . ?
O3 Cl2 O4 109.18(15) . . ?
O3 Cl2 O2 110.56(17) . . ?
O4 Cl2 O2 107.98(17) . . ?
O3 Cl2 O1 110.25(12) . . ?
O4 Cl2 O1 110.39(12) . . ?
O2 Cl2 O1 108.45(12) . . ?
C1 N1 N2 106.42(18) . . ?
C1 N1 Cu1 142.35(17) . . ?
N2 N1 Cu1 111.21(13) . . ?
C3 N2 N1 110.85(19) . . ?
C3 N2 C4 132.1(2) . . ?
N1 N2 C4 117.05(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C2 C1 106.8(2) . . ?
C3 C2 Cl1 127.1(2) . . ?
C1 C2 Cl1 126.1(2) . . ?
C2 C3 N2 106.3(2) . . ?
C2 C3 H3A 126.9 . . ?
N2 C3 H3A 126.9 . . ?
N3 C4 N2 114.3(2) . . ?
N3 C4 C5 128.3(2) . . ?
N2 C4 C5 117.3(2) . . ?
N1 C1 C2 109.7(2) . . ?
N1 C1 H1 125.2 . . ?
C2 C1 H1 125.2 . . ?
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
O1 Cl2 1.4455(17) . ?
O1 Cu1 2.6123(17) . ?
N3 C4 1.266(3) . ?
N3 Cu1 1.9688(19) . ?
N3 H3 0.8600 . ?
Cl1 C2 1.713(2) . ?
Cu1 N1 1.9762(19) 2_667 ?
Cu1 N1 1.9762(19) . ?
Cl2 O3 1.417(2) . ?
Cl2 O4 1.419(2) . ?
Cl2 O2 1.424(2) . ?
N1 C1 1.313(3) . ?
N1 N2 1.363(3) . ?
N2 C3 1.358(3) . ?
N2 C4 1.403(3) . ?
C5 C4 1.481(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 C3 1.356(3) . ?
C2 C1 1.406(3) . ?
C3 H3A 0.9300 . ?
C1 H1 0.9300 . ?
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
Cu1 O1 Cl2 O3 162.75(15) . . . . ?
Cu1 O1 Cl2 O4 42.04(18) . . . . ?
Cu1 O1 Cl2 O2 -76.07(19) . . . . ?
C1 N1 N2 C3 -0.1(2) . . . . ?
Cu1 N1 N2 C3 178.60(14) . . . . ?
C1 N1 N2 C4 -179.51(19) . . . . ?
Cu1 N1 N2 C4 -0.8(2) . . . . ?
C1 C2 C3 N2 -0.7(3) . . . . ?
Cl1 C2 C3 N2 176.69(17) . . . . ?
N1 N2 C3 C2 0.5(2) . . . . ?
C4 N2 C3 C2 179.8(2) . . . . ?
Cu1 N3 C4 N2 4.8(3) . . . . ?
Cu1 N3 C4 C5 -173.69(19) . . . . ?
C3 N2 C4 N3 178.1(2) . . . . ?
N1 N2 C4 N3 -2.6(3) . . . . ?
C3 N2 C4 C5 -3.2(4) . . . . ?
N1 N2 C4 C5 176.12(19) . . . . ?
N2 N1 C1 C2 -0.4(2) . . . . ?
Cu1 N1 C1 C2 -178.36(19) . . . . ?
C3 C2 C1 N1 0.7(3) . . . . ?
Cl1 C2 C1 N1 -176.73(17) . . . . ?
