#------------------------------------------------------------------------------
#$Date: 2025-03-04 22:23:36 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/76/7717689.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_7717689
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                81.015(2)
_cell_angle_beta                 84.024(2)
_cell_angle_gamma                68.617(2)
_cell_formula_units_Z            1
_cell_length_a                   7.0595(2)
_cell_length_b                   7.7575(2)
_cell_length_c                   9.7194(3)
_cell_measurement_reflns_used    3333
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.84
_cell_volume                     488.91(3)
_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 0.987
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7716
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.705
_diffrn_reflns_theta_min         2.124
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_T_max  0.837
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0319
_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+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2209
_reflns_number_total             2501
_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               7717689
_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 0.2428(3) 1.2507(2) 0.34833(17) 0.0339(4) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 1.000000 0.500000 0.01805(14) Uani 1 2 d S . P . .
Cl2 Cl 0.18349(8) 1.24717(7) 0.21081(5) 0.02059(15) Uani 1 1 d . . . . .
Cl1 Cl 0.18880(8) 0.68745(8) 0.47686(6) 0.02666(16) Uani 1 1 d . . . . .
C2 C 0.4698(4) 0.6009(3) 0.2523(2) 0.0247(5) Uani 1 1 d . . . . .
H2 H 0.422781 0.516592 0.217498 0.030 Uiso 1 1 calc R U . . .
N1 N 0.4952(3) 0.8006(2) 0.39037(17) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.3915(3) 0.6957(3) 0.3699(2) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.6273(3) 0.6567(3) 0.1997(2) 0.0236(4) Uani 1 1 d . . . . .
H3 H 0.711550 0.619812 0.118757 0.028 Uiso 1 1 calc R U . . .
N3 N 0.7182(3) 1.0021(2) 0.35754(18) 0.0201(4) Uani 1 1 d . . . . .
H3A H 0.785494 1.078124 0.356249 0.024 Uiso 1 1 calc R U . . .
N2 N 0.6420(3) 0.7745(2) 0.28387(18) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.7586(3) 0.8899(3) 0.2673(2) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.9084(4) 0.8698(4) 0.1479(2) 0.0275(5) Uani 1 1 d . . . . .
H5A H 0.992492 0.944265 0.154524 0.041 Uiso 1 1 calc R U . . .
H5B H 0.836856 0.913404 0.060875 0.041 Uiso 1 1 calc R U . . .
H5C H 0.995513 0.738183 0.148958 0.041 Uiso 1 1 calc R U . . .
O2 O 0.1727(3) 1.4179(3) 0.12468(19) 0.0383(4) Uani 1 1 d . . . . .
O4 O -0.0159(3) 1.2341(3) 0.2205(2) 0.0475(5) Uani 1 1 d . . . . .
O3 O 0.3269(3) 1.0932(3) 0.1490(2) 0.0461(5) Uani 1 1 d . . . . .
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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 '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'
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 129.41(10) . . ?
N3 Cu1 N3 180.0 . 2_676 ?
N3 Cu1 N1 79.92(7) . . ?
N3 Cu1 N1 100.08(7) 2_676 . ?
N3 Cu1 N1 100.08(7) . 2_676 ?
N3 Cu1 N1 79.92(7) 2_676 2_676 ?
N1 Cu1 N1 180.0 . 2_676 ?
N3 Cu1 O1 90.48(7) . . ?
N3 Cu1 O1 89.52(7) 2_676 . ?
N1 Cu1 O1 91.53(6) . . ?
N1 Cu1 O1 88.46(6) 2_676 . ?
O3 Cl2 O2 109.62(13) . . ?
O3 Cl2 O4 109.84(14) . . ?
O2 Cl2 O4 107.72(13) . . ?
O3 Cl2 O1 110.44(10) . . ?
O2 Cl2 O1 109.33(11) . . ?
O4 Cl2 O1 109.84(12) . . ?
C3 C2 C1 104.8(2) . . ?
C3 C2 H2 127.6 . . ?
C1 C2 H2 127.6 . . ?
C1 N1 N2 104.24(16) . . ?
C1 N1 Cu1 144.64(15) . . ?
N2 N1 Cu1 110.55(12) . . ?
N1 C1 C2 111.9(2) . . ?
N1 C1 Cl1 121.00(17) . . ?
C2 C1 Cl1 127.04(17) . . ?
N2 C3 C2 107.4(2) . . ?
N2 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
C4 N3 Cu1 117.61(15) . . ?
C4 N3 H3A 121.2 . . ?
Cu1 N3 H3A 121.2 . . ?
C3 N2 N1 111.62(17) . . ?
C3 N2 C4 130.69(18) . . ?
N1 N2 C4 116.91(16) . . ?
N3 C4 N2 114.97(19) . . ?
N3 C4 C5 128.0(2) . . ?
N2 C4 C5 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 . . ?
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 1.4486(16) . ?
O1 Cu1 2.5178(16) . ?
Cu1 N3 1.9638(18) . ?
Cu1 N3 1.9638(18) 2_676 ?
Cu1 N1 2.0221(17) . ?
Cu1 N1 2.0221(17) 2_676 ?
Cl2 O3 1.4238(18) . ?
Cl2 O2 1.4333(18) . ?
Cl2 O4 1.440(2) . ?
Cl1 C1 1.694(2) . ?
C2 C3 1.360(3) . ?
C2 C1 1.410(3) . ?
C2 H2 0.9500 . ?
N1 C1 1.324(3) . ?
N1 N2 1.369(2) . ?
C3 N2 1.355(3) . ?
C3 H3 0.9500 . ?
N3 C4 1.270(3) . ?
N3 H3A 0.8800 . ?
N2 C4 1.403(3) . ?
C4 C5 1.473(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
