#------------------------------------------------------------------------------
#$Date: 2025-03-04 22:23:36 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/76/7717698.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_7717698
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            'C12 H18 Cl2 Cu N6 O8'
_chemical_formula_weight         508.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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
_cell_angle_beta                 92.850(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3447(3)
_cell_length_b                   13.7312(7)
_cell_length_c                   13.2253(6)
_cell_measurement_reflns_used    2911
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.97
_cell_volume                     969.39(9)
_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 0.999
_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  0.0546
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.741
_diffrn_reflns_theta_min         2.139
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0441
_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+0.2908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2019
_reflns_number_total             2510
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02904f2.cif
_cod_data_source_block           1d'
_cod_depositor_comments
'Adding full bibliography for 7717689--7717702.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7717698
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.2907(5) 1.01037(18) 0.15670(19) 0.0314(6) Uani 1 1 d . . . . .
Cu1 Cu 0.000000 1.000000 0.000000 0.01770(17) Uani 1 2 d S . P . .
Cl1 Cl 0.23212(13) 1.06318(5) 0.24851(5) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.3592(5) 1.0177(2) 0.33374(19) 0.0374(6) Uani 1 1 d . . . . .
O2 O -0.0324(4) 1.06145(17) 0.25878(17) 0.0260(5) Uani 1 1 d . . . . .
O4 O 0.3180(5) 1.16176(18) 0.2386(2) 0.0342(6) Uani 1 1 d . . . . .
N1 N 0.1028(5) 0.86271(17) -0.01738(19) 0.0189(5) Uani 1 1 d . . . . .
N2 N -0.0371(5) 0.80167(18) 0.03803(19) 0.0178(5) Uani 1 1 d . . . . .
N3 N -0.2414(4) 0.93582(18) 0.08504(18) 0.0194(5) Uani 1 1 d . . . . .
H3 H -0.358643 0.968995 0.114326 0.023 Uiso 1 1 calc R U . . .
C3 C 0.0307(6) 0.7067(2) 0.0236(2) 0.0245(6) Uani 1 1 d . . . . .
H3A H -0.040312 0.651069 0.053809 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2189(6) 0.7068(2) -0.0421(2) 0.0232(6) Uani 1 1 d . . . . .
C4 C 0.3611(7) 0.6209(3) -0.0796(3) 0.0342(8) Uani 1 1 d . . . . .
H4A H 0.414365 0.579390 -0.022250 0.051 Uiso 1 1 calc R U . . .
H4B H 0.508816 0.643778 -0.113732 0.051 Uiso 1 1 calc R U . . .
H4C H 0.253138 0.583481 -0.127418 0.051 Uiso 1 1 calc R U . . .
C1 C 0.2567(6) 0.8054(2) -0.0659(2) 0.0211(6) Uani 1 1 d . . . . .
H1 H 0.377090 0.828043 -0.110830 0.025 Uiso 1 1 calc R U . . .
C5 C -0.2207(5) 0.8443(2) 0.0959(2) 0.0178(6) Uani 1 1 d . . . . .
C6 C -0.3620(6) 0.7802(3) 0.1632(2) 0.0260(7) Uani 1 1 d . . . . .
H6A H -0.481147 0.819389 0.199836 0.039 Uiso 1 1 calc R U . . .
H6B H -0.244843 0.748000 0.211767 0.039 Uiso 1 1 calc R U . . .
H6C H -0.453227 0.730940 0.122408 0.039 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
Cl1 O1 Cu1 124.04(13) . . ?
N3 Cu1 N3 180.00(10) . 3_575 ?
N3 Cu1 N1 99.61(10) . 3_575 ?
N3 Cu1 N1 80.40(10) 3_575 3_575 ?
N3 Cu1 N1 80.39(10) . . ?
N3 Cu1 N1 99.61(10) 3_575 . ?
N1 Cu1 N1 180.00(4) 3_575 . ?
N3 Cu1 O1 87.16(9) . . ?
N3 Cu1 O1 92.85(9) 3_575 . ?
N1 Cu1 O1 90.80(9) 3_575 . ?
N1 Cu1 O1 89.20(9) . . ?
O2 Cl1 O3 110.58(16) . . ?
O2 Cl1 O4 110.29(15) . . ?
O3 Cl1 O4 109.97(17) . . ?
O2 Cl1 O1 108.97(14) . . ?
O3 Cl1 O1 108.98(16) . . ?
O4 Cl1 O1 107.99(16) . . ?
C1 N1 N2 105.4(2) . . ?
C1 N1 Cu1 143.4(2) . . ?
N2 N1 Cu1 111.14(18) . . ?
N1 N2 C3 110.8(2) . . ?
N1 N2 C5 117.0(2) . . ?
C3 N2 C5 132.2(3) . . ?
C5 N3 Cu1 117.0(2) . . ?
C5 N3 H3 121.5 . . ?
Cu1 N3 H3 121.5 . . ?
C2 C3 N2 107.3(3) . . ?
C2 C3 H3A 126.4 . . ?
N2 C3 H3A 126.4 . . ?
C3 C2 C1 105.2(3) . . ?
C3 C2 C4 127.8(3) . . ?
C1 C2 C4 127.0(3) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C1 C2 111.3(3) . . ?
N1 C1 H1 124.3 . . ?
C2 C1 H1 124.3 . . ?
N3 C5 N2 114.3(3) . . ?
N3 C5 C6 127.7(3) . . ?
N2 C5 C6 118.0(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
O1 Cl1 1.461(2) . ?
O1 Cu1 2.532(2) . ?
Cu1 N3 1.962(2) . ?
Cu1 N3 1.962(2) 3_575 ?
Cu1 N1 1.980(2) 3_575 ?
Cu1 N1 1.980(2) . ?
Cl1 O2 1.427(2) . ?
Cl1 O3 1.430(3) . ?
Cl1 O4 1.437(3) . ?
N1 C1 1.326(4) . ?
N1 N2 1.361(3) . ?
N2 C3 1.370(4) . ?
N2 C5 1.402(4) . ?
N3 C5 1.268(4) . ?
N3 H3 0.8800 . ?
C3 C2 1.361(5) . ?
C3 H3A 0.9500 . ?
C2 C1 1.407(4) . ?
C2 C4 1.501(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C1 H1 0.9500 . ?
C5 C6 1.485(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
Cu1 O1 Cl1 O2 30.4(2) . . . . ?
Cu1 O1 Cl1 O3 151.19(18) . . . . ?
Cu1 O1 Cl1 O4 -89.37(19) . . . . ?
C1 N1 N2 C3 0.0(3) . . . . ?
Cu1 N1 N2 C3 178.4(2) . . . . ?
C1 N1 N2 C5 -178.9(2) . . . . ?
Cu1 N1 N2 C5 -0.4(3) . . . . ?
N1 N2 C3 C2 0.3(3) . . . . ?
C5 N2 C3 C2 178.9(3) . . . . ?
N2 C3 C2 C1 -0.4(3) . . . . ?
N2 C3 C2 C4 178.2(3) . . . . ?
N2 N1 C1 C2 -0.2(3) . . . . ?
Cu1 N1 C1 C2 -177.8(3) . . . . ?
C3 C2 C1 N1 0.4(4) . . . . ?
C4 C2 C1 N1 -178.2(3) . . . . ?
Cu1 N3 C5 N2 -4.7(3) . . . . ?
Cu1 N3 C5 C6 173.7(2) . . . . ?
N1 N2 C5 N3 3.3(4) . . . . ?
C3 N2 C5 N3 -175.2(3) . . . . ?
N1 N2 C5 C6 -175.3(3) . . . . ?
C3 N2 C5 C6 6.2(5) . . . . ?
