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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/4/12/58/4125837.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_4125837
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         'C34 H16 Cl8 Cu2 F12 N4 O2'
_chemical_formula_sum            'C34 H16 Cl8 Cu2 F12 N4 O2'
_chemical_formula_weight         1151.19
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.815(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4145(3)
_cell_length_b                   17.6411(4)
_cell_length_c                   18.8543(5)
_cell_measurement_reflns_used    7762
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.17
_cell_volume                     4080.42(17)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.022
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2264
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4175
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0311P)²+2.0427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3371
_reflns_number_total             4175
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11332_si_006.cif
_cod_data_source_block           tryC2c
_cod_database_code               4125837
_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   0.777
_shelx_estimated_absorpt_t_max   0.907
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
Cu1 Cu 0.43293(2) 0.12971(2) 0.67625(2) 0.01268(8) Uani 1 1 d . .
Cl1 Cl 0.61596(5) 0.04963(3) 0.53462(3) 0.02494(14) Uani 1 1 d . .
Cl2 Cl 0.50005(5) 0.31762(3) 0.63736(3) 0.02766(15) Uani 1 1 d . .
Cl3 Cl 0.13076(5) 0.16852(4) 0.71931(3) 0.02789(15) Uani 1 1 d . .
Cl4 Cl 0.39072(5) -0.06363(3) 0.67171(3) 0.02544(15) Uani 1 1 d . .
F1 F 0.31605(11) 0.20572(8) 0.40568(7) 0.0229(3) Uani 1 1 d . .
F2 F 0.44666(11) 0.26840(7) 0.46602(7) 0.0216(3) Uani 1 1 d . .
F3 F 0.47730(11) 0.15867(8) 0.42383(7) 0.0241(3) Uani 1 1 d . .
F4 F 0.09774(11) 0.04924(8) 0.48364(7) 0.0261(3) Uani 1 1 d . .
F5 F 0.15032(11) -0.02934(7) 0.56800(8) 0.0252(3) Uani 1 1 d . .
F6 F 0.05467(10) 0.06776(8) 0.58795(8) 0.0254(3) Uani 1 1 d . .
O1 O 0.58034(12) 0.13292(10) 0.72381(8) 0.0183(4) Uani 1 1 d D .
H1 H 0.6350(16) 0.1323(16) 0.7087(15) 0.027 Uiso 1 1 d D U
N1 N 0.45798(14) 0.16166(10) 0.58139(10) 0.0132(4) Uani 1 1 d . .
N2 N 0.28989(14) 0.08680(10) 0.64217(10) 0.0132(4) Uani 1 1 d . .
C1 C 0.38177(18) 0.16156(12) 0.52392(11) 0.0128(4) Uani 1 1 d . .
C2 C 0.28014(17) 0.12808(12) 0.52006(11) 0.0122(4) Uani 1 1 d . .
H2 H 0.2325 0.1321 0.4757 0.015 Uiso 1 1 calc R U
C3 C 0.24100(17) 0.08890(12) 0.57537(12) 0.0125(4) Uani 1 1 d . .
C4 C 0.40572(18) 0.19872(13) 0.45486(12) 0.0162(5) Uani 1 1 d . .
C5 C 0.13512(18) 0.04405(13) 0.55370(12) 0.0164(5) Uani 1 1 d . .
C6 C 0.56582(17) 0.18870(12) 0.57974(11) 0.0132(4) Uani 1 1 d . .
C7 C 0.64762(18) 0.14187(13) 0.56165(12) 0.0165(5) Uani 1 1 d . .
C8 C 0.75524(19) 0.16594(15) 0.56793(13) 0.0224(5) Uani 1 1 d . .
H8 H 0.8096 0.1333 0.5547 0.027 Uiso 1 1 calc R U
C9 C 0.7823(2) 0.23784(16) 0.59367(13) 0.0267(6) Uani 1 1 d . .
H9 H 0.8556 0.2547 0.5978 0.032 Uiso 1 1 calc R U
C10 C 0.7036(2) 0.28543(14) 0.61340(13) 0.0237(6) Uani 1 1 d . .
H10 H 0.7226 0.3349 0.6310 0.028 Uiso 1 1 calc R U
C11 C 0.59692(19) 0.26041(13) 0.60720(12) 0.0178(5) Uani 1 1 d . .
C12 C 0.24778(18) 0.04425(13) 0.69622(12) 0.0162(5) Uani 1 1 d . .
C13 C 0.17397(19) 0.07619(15) 0.73675(13) 0.0211(5) Uani 1 1 d . .
C14 C 0.1397(2) 0.03677(17) 0.79291(13) 0.0298(6) Uani 1 1 d . .
H14 H 0.0886 0.0588 0.8195 0.036 Uiso 1 1 calc R U
C15 C 0.1808(2) -0.03476(17) 0.80973(14) 0.0344(7) Uani 1 1 d . .
H15 H 0.1564 -0.0623 0.8476 0.041 Uiso 1 1 calc R U
C16 C 0.2568(2) -0.06693(16) 0.77241(14) 0.0296(6) Uani 1 1 d . .
H16 H 0.2855 -0.1159 0.7849 0.035 Uiso 1 1 calc R U
C17 C 0.29059(19) -0.02698(14) 0.71658(12) 0.0201(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'
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
O1 Cu1 O1 76.02(7) . 2_656
O1 Cu1 N1 98.41(7) . .
O1 Cu1 N1 160.90(8) 2_656 .
O1 Cu1 N2 157.79(8) . .
O1 Cu1 N2 97.15(7) 2_656 .
N1 Cu1 N2 94.33(7) . .
O1 Cu1 Cu1 38.13(5) . 2_656
O1 Cu1 Cu1 37.99(5) 2_656 2_656
N1 Cu1 Cu1 134.80(5) . 2_656
N2 Cu1 Cu1 130.66(5) . 2_656
Cu1 O1 Cu1 103.88(7) . 2_656
Cu1 O1 H1 131(2) . .
Cu1 O1 H1 125(2) 2_656 .
C1 N1 C6 122.53(18) . .
C1 N1 Cu1 123.84(14) . .
C6 N1 Cu1 113.57(13) . .
C3 N2 C12 122.26(18) . .
C3 N2 Cu1 124.77(15) . .
C12 N2 Cu1 112.59(13) . .
N1 C1 C2 125.0(2) . .
N1 C1 C4 119.26(18) . .
C2 C1 C4 115.67(19) . .
C1 C2 C3 126.1(2) . .
C1 C2 H2 116.9 . .
C3 C2 H2 116.9 . .
N2 C3 C2 124.6(2) . .
N2 C3 C5 119.49(19) . .
C2 C3 C5 115.94(19) . .
F2 C4 F3 107.03(17) . .
F2 C4 F1 106.25(17) . .
F3 C4 F1 106.43(17) . .
F2 C4 C1 112.35(18) . .
F3 C4 C1 112.05(18) . .
F1 C4 C1 112.31(17) . .
F5 C5 F4 106.53(18) . .
F5 C5 F6 107.46(18) . .
F4 C5 F6 106.52(18) . .
F5 C5 C3 111.02(18) . .
F4 C5 C3 112.45(18) . .
F6 C5 C3 112.51(18) . .
C7 C6 C11 117.2(2) . .
C7 C6 N1 121.98(19) . .
C11 C6 N1 120.1(2) . .
C8 C7 C6 121.7(2) . .
C8 C7 Cl1 118.95(18) . .
C6 C7 Cl1 119.25(17) . .
C9 C8 C7 119.3(2) . .
C9 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
C8 C9 C10 120.6(2) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C9 C10 C11 119.4(2) . .
C9 C10 H10 120.3 . .
C11 C10 H10 120.3 . .
C10 C11 C6 121.7(2) . .
C10 C11 Cl2 119.36(19) . .
C6 C11 Cl2 118.86(18) . .
C17 C12 C13 117.8(2) . .
C17 C12 N2 120.3(2) . .
C13 C12 N2 121.4(2) . .
C14 C13 C12 121.2(2) . .
C14 C13 Cl3 119.7(2) . .
C12 C13 Cl3 119.04(18) . .
C15 C14 C13 119.3(3) . .
C15 C14 H14 120.4 . .
C13 C14 H14 120.4 . .
C14 C15 C16 121.0(2) . .
C14 C15 H15 119.5 . .
C16 C15 H15 119.5 . .
C15 C16 C17 119.2(3) . .
C15 C16 H16 120.4 . .
C17 C16 H16 120.4 . .
C16 C17 C12 121.4(2) . .
C16 C17 Cl4 120.3(2) . .
C12 C17 Cl4 118.26(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9114(16) .
Cu1 O1 1.9173(16) 2_656
Cu1 N1 1.9452(18) .
Cu1 N2 1.9466(18) .
Cu1 Cu1 3.0145(5) 2_656
Cl1 C7 1.732(2) .
Cl2 C11 1.731(2) .
Cl3 C13 1.730(3) .
Cl4 C17 1.732(3) .
F1 C4 1.341(3) .
F2 C4 1.335(3) .
F3 C4 1.338(3) .
F4 C5 1.334(3) .
F5 C5 1.330(3) .
F6 C5 1.337(3) .
O1 Cu1 1.9172(16) 2_656
O1 H1 0.775(17) .
N1 C1 1.325(3) .
N1 C6 1.426(3) .
N2 C3 1.312(3) .
N2 C12 1.428(3) .
C1 C2 1.385(3) .
C1 C4 1.527(3) .
C2 C3 1.399(3) .
C2 H2 0.9500 .
C3 C5 1.535(3) .
C6 C7 1.391(3) .
C6 C11 1.399(3) .
C7 C8 1.390(3) .
C8 C9 1.381(4) .
C8 H8 0.9500 .
C9 C10 1.381(4) .
C9 H9 0.9500 .
C10 C11 1.384(3) .
C10 H10 0.9500 .
C12 C17 1.395(3) .
C12 C13 1.398(3) .
C13 C14 1.387(3) .
C14 C15 1.380(4) .
C14 H14 0.9500 .
C15 C16 1.383(4) .
C15 H15 0.9500 .
C16 C17 1.384(3) .
C16 H16 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125217
