#------------------------------------------------------------------------------
#$Date: 2025-03-04 22:23:36 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/76/7717694.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_7717694
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 Cl2 Cu I2 N6 O8'
_chemical_formula_weight         732.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-12-13 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.5270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9186(3)
_cell_length_b                   11.1291(3)
_cell_length_c                   13.1374(4)
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.53
_cell_volume                     1026.69(6)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0712
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11452
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.531
_exptl_absorpt_coefficient_mu    4.382
_exptl_absorpt_correction_T_max  0.616
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    2.369
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.262
_refine_diff_density_min         -1.106
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0376
_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)+(0.0469P)²+0.4163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0956
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1423
_reflns_number_total             1804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02904f2.cif
_cod_data_source_block           1c
_cod_depositor_comments
'Adding full bibliography for 7717689--7717702.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7717694
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 1.00398(6) 0.68206(4) 0.58724(4) 0.03632(19) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.0292(3) Uani 1 2 d S . P . .
Cl1 Cl 0.6788(2) 0.20749(15) 0.59431(14) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.6605(7) 0.2350(5) 0.6950(4) 0.0477(14) Uani 1 1 d . . . . .
N1 N 0.6458(7) 0.5656(4) 0.4182(4) 0.0257(12) Uani 1 1 d . . . . .
N3 N 0.3276(8) 0.4545(5) 0.3396(5) 0.0328(13) Uani 1 1 d . . . . .
H3 H 0.226261 0.413538 0.323567 0.039 Uiso 1 1 calc R U . . .
N2 N 0.5437(7) 0.5417(5) 0.3013(4) 0.0260(12) Uani 1 1 d . . . . .
O2 O 0.8441(8) 0.1380(5) 0.6215(5) 0.0610(16) Uani 1 1 d . . . . .
O1 O 0.6875(10) 0.3145(5) 0.5394(6) 0.072(2) Uani 1 1 d . . . . .
C4 C 0.3659(9) 0.4850(6) 0.2629(6) 0.0280(15) Uani 1 1 d . . . . .
C1 C 0.7945(9) 0.6255(6) 0.4291(6) 0.0287(15) Uani 1 1 d . . . . .
C3 C 0.6351(9) 0.5892(6) 0.2458(6) 0.0305(16) Uani 1 1 d . . . . .
H3A H 0.594981 0.584876 0.167242 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7934(10) 0.6435(6) 0.3231(6) 0.0327(16) Uani 1 1 d . . . . .
H2 H 0.883329 0.684490 0.309500 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2519(9) 0.4724(6) 0.1362(5) 0.0320(16) Uani 1 1 d . . . . .
H5A H 0.128422 0.440790 0.118104 0.048 Uiso 1 1 calc R U . . .
H5B H 0.315735 0.418719 0.108112 0.048 Uiso 1 1 calc R U . . .
H5C H 0.237981 0.549691 0.100672 0.048 Uiso 1 1 calc R U . . .
O4 O 0.5182(10) 0.1415(7) 0.5210(6) 0.093(3) 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'
H H 0.0000 0.0000 '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'
I I -0.4742 1.8119 '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'
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 3_666 . ?
N3 Cu1 N1 100.9(2) 3_666 . ?
N3 Cu1 N1 79.1(2) . . ?
N3 Cu1 N1 79.1(2) 3_666 3_666 ?
N3 Cu1 N1 100.9(2) . 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
N3 Cu1 O1 86.4(2) 3_666 . ?
N3 Cu1 O1 93.6(2) . . ?
N1 Cu1 O1 88.71(18) . . ?
N1 Cu1 O1 91.29(19) 3_666 . ?
O4 Cl1 O1 109.6(5) . . ?
O4 Cl1 O2 109.1(4) . . ?
O1 Cl1 O2 109.4(4) . . ?
O4 Cl1 O3 107.5(4) . . ?
O1 Cl1 O3 110.0(3) . . ?
O2 Cl1 O3 111.2(3) . . ?
C1 N1 N2 104.7(5) . . ?
C1 N1 Cu1 145.9(5) . . ?
N2 N1 Cu1 109.3(4) . . ?
C4 N3 Cu1 119.6(5) . . ?
C4 N3 H3 120.2 . . ?
Cu1 N3 H3 120.2 . . ?
C3 N2 N1 109.7(5) . . ?
C3 N2 C4 132.8(6) . . ?
N1 N2 C4 117.2(5) . . ?
Cl1 O1 Cu1 130.6(3) . . ?
N3 C4 N2 114.6(6) . . ?
N3 C4 C5 129.8(6) . . ?
N2 C4 C5 115.6(5) . . ?
N1 C1 C2 111.9(6) . . ?
N1 C1 I1 122.1(5) . . ?
C2 C1 I1 126.0(5) . . ?
C2 C3 N2 108.3(6) . . ?
C2 C3 H3A 125.8 . . ?
N2 C3 H3A 125.8 . . ?
C3 C2 C1 105.3(6) . . ?
C3 C2 H2 127.4 . . ?
C1 C2 H2 127.4 . . ?
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
I1 C1 2.068(7) . ?
Cu1 N3 1.976(5) 3_666 ?
Cu1 N3 1.976(5) . ?
Cu1 N1 2.042(5) . ?
Cu1 N1 2.042(5) 3_666 ?
Cu1 O1 2.454(5) . ?
Cl1 O4 1.398(6) . ?
Cl1 O1 1.410(5) . ?
Cl1 O2 1.417(5) . ?
Cl1 O3 1.429(5) . ?
N1 C1 1.302(8) . ?
N1 N2 1.391(7) . ?
N3 C4 1.227(8) . ?
N3 H3 0.8600 . ?
N2 C3 1.350(7) . ?
N2 C4 1.406(8) . ?
C4 C5 1.488(9) . ?
C1 C2 1.402(9) . ?
C3 C2 1.339(9) . ?
C3 H3A 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
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 -0.4(7) . . . . ?
Cu1 N1 N2 C3 177.4(4) . . . . ?
C1 N1 N2 C4 -175.2(5) . . . . ?
Cu1 N1 N2 C4 2.6(6) . . . . ?
O4 Cl1 O1 Cu1 74.6(6) . . . . ?
O2 Cl1 O1 Cu1 -165.9(5) . . . . ?
O3 Cl1 O1 Cu1 -43.5(6) . . . . ?
Cu1 N3 C4 N2 5.7(8) . . . . ?
Cu1 N3 C4 C5 -173.5(5) . . . . ?
C3 N2 C4 N3 -178.8(6) . . . . ?
N1 N2 C4 N3 -5.4(8) . . . . ?
C3 N2 C4 C5 0.5(10) . . . . ?
N1 N2 C4 C5 173.9(5) . . . . ?
N2 N1 C1 C2 0.7(7) . . . . ?
Cu1 N1 C1 C2 -175.5(6) . . . . ?
N2 N1 C1 I1 -178.3(4) . . . . ?
Cu1 N1 C1 I1 5.4(11) . . . . ?
N1 N2 C3 C2 -0.2(7) . . . . ?
C4 N2 C3 C2 173.6(6) . . . . ?
N2 C3 C2 C1 0.6(7) . . . . ?
N1 C1 C2 C3 -0.9(8) . . . . ?
I1 C1 C2 C3 178.2(5) . . . . ?
