#------------------------------------------------------------------------------
#$Date: 2025-03-04 22:23:36 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298284 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/76/7717696.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_7717696
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 Br2 Cl2 Cu N6 O8'
_chemical_formula_weight         638.51
_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                 97.897(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8326(4)
_cell_length_b                   10.9412(7)
_cell_length_c                   11.5905(7)
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.61
_cell_measurement_theta_min      2.57
_cell_volume                     983.86(10)
_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 0.999
_diffrn_measured_fraction_theta_max 0.983
_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  0.1193
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.952
_diffrn_reflns_theta_min         2.572
_exptl_absorpt_coefficient_mu    5.496
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.811
_refine_diff_density_min         -1.244
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.244
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0439
_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)+0.9132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2072
_reflns_number_total             2559
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02904f2.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 7717689--7717702.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7717696
_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
Br1 Br 0.08671(4) 0.32339(4) 0.57776(3) 0.02784(13) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.02014(16) Uani 1 2 d S . P . .
Cl1 Cl 0.58289(10) 0.20556(9) 0.39757(7) 0.0223(2) Uani 1 1 d D . . . .
O3 O 0.4651(3) 0.2372(3) 0.29780(18) 0.0338(7) Uani 1 1 d D . . . .
O1 O 0.6558(3) 0.3137(3) 0.4551(3) 0.0380(7) Uani 1 1 d . . . . .
N3 N 0.5171(4) 0.5466(3) 0.3375(3) 0.0230(7) Uani 1 1 d . . . . .
H3 H 0.604070 0.587619 0.320616 0.028 Uiso 1 1 calc R U . . .
N2 N 0.2570(3) 0.4603(3) 0.3020(3) 0.0205(6) Uani 1 1 d . . . . .
N1 N 0.2724(3) 0.4375(3) 0.4191(2) 0.0190(6) Uani 1 1 d . . . . .
O4 O 0.7193(3) 0.1324(3) 0.3635(3) 0.0452(8) Uani 1 1 d . . . . .
O2 O 0.4934(4) 0.1383(3) 0.4749(3) 0.0522(9) Uani 1 1 d . . . . .
C1 C 0.1301(4) 0.3766(4) 0.4321(3) 0.0231(8) Uani 1 1 d . . . . .
C4 C 0.3989(4) 0.5153(4) 0.2598(3) 0.0214(8) Uani 1 1 d . . . . .
C3 C 0.1080(4) 0.4127(4) 0.2443(3) 0.0237(8) Uani 1 1 d . . . . .
H3A H 0.071655 0.416177 0.164503 0.028 Uiso 1 1 calc R U . . .
C2 C 0.0229(4) 0.3593(4) 0.3258(3) 0.0266(8) Uani 1 1 d . . . . .
H2 H -0.083290 0.319864 0.313749 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3885(5) 0.5256(4) 0.1311(3) 0.0272(9) Uani 1 1 d . . . . .
H5A H 0.490095 0.565440 0.111965 0.041 Uiso 1 1 calc R U . . .
H5B H 0.288624 0.572558 0.101123 0.041 Uiso 1 1 calc R U . . .
H5C H 0.379934 0.445423 0.097147 0.041 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'
Br Br -0.2901 2.4595 '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'
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 180.00(5) 3_666 . ?
N3 Cu1 N1 100.63(11) 3_666 . ?
N3 Cu1 N1 79.37(11) . . ?
N3 Cu1 N1 79.37(11) 3_666 3_666 ?
N3 Cu1 N1 100.63(11) . 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
N3 Cu1 O1 95.04(12) 3_666 . ?
N3 Cu1 O1 84.96(12) . . ?
N1 Cu1 O1 93.05(11) . . ?
N1 Cu1 O1 86.95(11) 3_666 . ?
O2 Cl1 O3 108.62(18) . . ?
O2 Cl1 O4 109.7(2) . . ?
O3 Cl1 O4 109.71(18) . . ?
O2 Cl1 O1 109.4(2) . . ?
O3 Cl1 O1 110.47(19) . . ?
O4 Cl1 O1 108.89(18) . . ?
Cl1 O1 Cu1 126.96(15) . . ?
C4 N3 Cu1 118.5(2) . . ?
C4 N3 H3 120.8 . . ?
Cu1 N3 H3 120.8 . . ?
C3 N2 N1 111.7(3) . . ?
C3 N2 C4 130.9(3) . . ?
N1 N2 C4 117.1(3) . . ?
C1 N1 N2 104.1(3) . . ?
C1 N1 Cu1 145.3(3) . . ?
N2 N1 Cu1 110.56(19) . . ?
N1 C1 C2 112.3(3) . . ?
N1 C1 Br1 121.4(3) . . ?
C2 C1 Br1 126.3(3) . . ?
N3 C4 N2 114.1(3) . . ?
N3 C4 C5 129.5(3) . . ?
N2 C4 C5 116.3(3) . . ?
C2 C3 N2 106.9(3) . . ?
C2 C3 H3A 126.5 . . ?
N2 C3 H3A 126.5 . . ?
C3 C2 C1 105.1(3) . . ?
C3 C2 H2 127.5 . . ?
C1 C2 H2 127.5 . . ?
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
Br1 C1 1.861(4) . ?
Cu1 N3 1.974(3) 3_666 ?
Cu1 N3 1.974(3) . ?
Cu1 N1 2.016(3) . ?
Cu1 N1 2.016(3) 3_666 ?
Cu1 O1 2.468(3) . ?
Cl1 O2 1.417(3) . ?
Cl1 O3 1.4194(16) . ?
Cl1 O4 1.433(3) . ?
Cl1 O1 1.437(3) . ?
N3 C4 1.248(4) . ?
N3 H3 0.8600 . ?
N2 C3 1.366(4) . ?
N2 N1 1.369(4) . ?
N2 C4 1.409(4) . ?
N1 C1 1.325(4) . ?
C1 C2 1.405(5) . ?
C4 C5 1.486(5) . ?
C3 C2 1.361(5) . ?
C3 H3A 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
