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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/58/4125836.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_4125836
loop_
_publ_author_name
'Kundu, Subrata'
'Kim, William Y.'
'Bertke, Jeffery A.'
'Warren, Timothy H.'
_publ_contact_author             'Timothy H. Warren'
_publ_section_title
;
 Copper(II) Activation of Nitrite: Nitrosation of Nucleophiles and
 Generation of NO by Thiols.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1045
_journal_page_last               1048
_journal_paper_doi               10.1021/jacs.6b11332
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C17 H7 Cl4 Cu F6 N3 O2'
_chemical_formula_sum            'C17 H7 Cl4 Cu F6 N3 O2'
_chemical_formula_weight         604.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.815(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5124(8)
_cell_length_b                   9.5784(6)
_cell_length_c                   18.2174(12)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.18
_cell_measurement_theta_min      2.24
_cell_volume                     2175.6(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_molecular_graphics    'SHELXTL v2014-4 (Bruker, 2014)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.190
_diffrn_reflns_theta_min         2.244
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0271
_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)+(0.0282P)²+3.7095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2653
_reflns_number_total             2916
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11332_si_002.cif
_cod_data_source_block           B15198
_cod_database_code               4125836
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.539
_shelx_estimated_absorpt_t_max   0.810
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cu1 Cu 0.5000 0.65978(3) 0.2500 0.01516(8) Uani 1 2 d S T P
Cl1 Cl 0.63077(3) 0.77072(4) 0.44305(2) 0.02207(10) Uani 1 1 d . . .
Cl2 Cl 0.23315(4) 0.68469(6) 0.31414(3) 0.03472(12) Uani 1 1 d . . .
F1 F 0.47329(12) 1.02459(12) 0.42974(6) 0.0430(3) Uani 1 1 d . . .
F2 F 0.31453(10) 0.98918(13) 0.37846(9) 0.0475(4) Uani 1 1 d . . .
F3 F 0.40812(8) 1.15785(10) 0.34353(5) 0.0219(2) Uani 1 1 d . . .
O1 O 0.48437(12) 0.47984(13) 0.30528(7) 0.0292(3) Uani 1 1 d . . .
N1 N 0.45757(10) 0.79205(14) 0.32038(7) 0.0143(2) Uani 1 1 d . . .
N2 N 0.5000 0.4041(2) 0.2500 0.0302(5) Uani 1 2 d S T P
C1 C 0.45923(11) 0.92843(16) 0.30966(8) 0.0132(3) Uani 1 1 d . . .
C2 C 0.5000 0.9954(2) 0.2500 0.0135(4) Uani 1 2 d S T P
H2 H 0.5000 1.0946 0.2500 0.016 Uiso 1 2 calc R U P
C3 C 0.41388(14) 1.02585(17) 0.36582(9) 0.0191(3) Uani 1 1 d . . .
C4 C 0.42599(12) 0.73214(15) 0.38685(8) 0.0138(3) Uani 1 1 d . . .
C5 C 0.49935(12) 0.71765(16) 0.44859(8) 0.0148(3) Uani 1 1 d . . .
C6 C 0.47027(14) 0.65807(17) 0.51342(9) 0.0201(3) Uani 1 1 d . . .
H6 H 0.5204 0.6526 0.5555 0.024 Uiso 1 1 calc R U .
C7 C 0.36764(15) 0.60691(18) 0.51601(10) 0.0243(4) Uani 1 1 d . . .
H7 H 0.3470 0.5670 0.5604 0.029 Uiso 1 1 calc R U .
C8 C 0.29425(14) 0.61281(18) 0.45480(10) 0.0246(4) Uani 1 1 d . . .
H8 H 0.2244 0.5747 0.4565 0.030 Uiso 1 1 calc R U .
C9 C 0.32415(13) 0.67509(17) 0.39093(9) 0.0194(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'
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'
F F 0.0171 0.0103 '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
N1 Cu1 N1 96.85(8) 2_655 .
N1 Cu1 O1 161.41(5) 2_655 .
N1 Cu1 O1 100.83(5) . .
N1 Cu1 O1 100.84(5) 2_655 2_655
N1 Cu1 O1 161.41(5) . 2_655
O1 Cu1 O1 62.30(7) . 2_655
N2 O1 Cu1 93.68(10) . .
C1 N1 C4 122.17(13) . .
C1 N1 Cu1 123.24(10) . .
C4 N1 Cu1 114.57(10) . .
O1 N2 O1 110.3(2) 2_655 .
N1 C1 C2 125.52(14) . .
N1 C1 C3 119.56(13) . .
C2 C1 C3 114.93(14) . .
C1 C2 C1 125.3(2) . 2_655
F1 C3 F3 106.79(13) . .
F1 C3 F2 107.96(14) . .
F3 C3 F2 106.06(14) . .
F1 C3 C1 111.68(13) . .
F3 C3 C1 112.96(12) . .
F2 C3 C1 111.07(13) . .
C9 C4 C5 117.36(14) . .
C9 C4 N1 121.53(14) . .
C5 C4 N1 120.89(13) . .
C6 C5 C4 121.63(15) . .
C6 C5 Cl1 119.23(12) . .
C4 C5 Cl1 119.11(11) . .
C7 C6 C5 119.14(16) . .
C6 C7 C8 120.95(15) . .
C7 C8 C9 119.06(16) . .
C8 C9 C4 121.71(16) . .
C8 C9 Cl2 119.71(13) . .
C4 C9 Cl2 118.58(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.9091(13) 2_655
Cu1 N1 1.9092(13) .
Cu1 O1 2.0140(12) .
Cu1 O1 2.0140(12) 2_655
Cl1 C5 1.7321(16) .
Cl2 C9 1.7305(17) .
F1 C3 1.328(2) .
F2 C3 1.330(2) .
F3 C3 1.3281(18) .
O1 N2 1.2693(17) .
N1 C1 1.321(2) .
N1 C4 1.4255(18) .
N2 O1 1.2693(17) 2_655
C1 C2 1.3949(17) .
C1 C3 1.529(2) .
C2 C1 1.3949(17) 2_655
C4 C9 1.394(2) .
C4 C5 1.398(2) .
C5 C6 1.387(2) .
C6 C7 1.379(3) .
C7 C8 1.385(3) .
C8 C9 1.387(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125216
