#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/65/7056570.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_7056570
loop_
_publ_author_name
'Budniak, Adam K.'
'Masny, Michał'
'Prezelj, Kristina'
'Grzeszkiewicz, Mikołaj'
'Gawraczyński, Jakub'
'Dobrzycki, Łukasz'
'Cyrański, Michał K.'
'Koźmiński, Wiktor'
'Mazej, Zoran'
'Fijałkowski, Karol J.'
'Grochala, Wojciech'
'Leszczyński, Piotr J.'
_publ_section_title
;
 Reconnaissance of reactivity of an Ag(ii)SO4 one-electron oxidizer
 towards naphthalene derivatives
;
_journal_issue                   19
_journal_name_full               'New J. Chem.'
_journal_page_first              10742
_journal_page_last               10749
_journal_paper_doi               10.1039/C7NJ02299A
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C20 H12 Br0.28 F1.72'
_chemical_formula_weight         307.50
_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_update_record
;
2017-07-27 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.098(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6575(11)
_cell_length_b                   10.6532(9)
_cell_length_c                   11.1899(10)
_cell_measurement_reflns_used    4790
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.4162
_cell_measurement_theta_min      2.6103
_cell_volume                     1366.4(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 V2014 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  TRIUMPH
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10373
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             629
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.325
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0515
_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)+(0.0077P)²+2.9193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                1246
_reflns_number_total             1407
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj02299a2.cif
_cod_data_source_block           10-1_in_C2c
_cod_database_code               7056570
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
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
Br1 Br 0.0485(4) 0.2827(5) 0.6182(4) 0.0276(8) Uani 0.141(2) 1 d . . P
F1 F 0.0728(4) 0.2929(4) 0.5966(4) 0.0332(10) Uani 0.859(2) 1 d . . P
C1 C 0.4353(2) 0.3008(2) 0.7257(2) 0.0255(5) Uani 1 1 d . . .
C2 C 0.3814(2) 0.2050(2) 0.7615(2) 0.0285(5) Uani 1 1 d . . .
H2 H 0.4280 0.1398 0.8167 0.034 Uiso 1 1 calc R U .
C3 C 0.2600(2) 0.2007(2) 0.7191(2) 0.0306(6) Uani 1 1 d . . .
H3 H 0.2248 0.1341 0.7456 0.037 Uiso 1 1 calc R U .
C4 C 0.1944(2) 0.2932(2) 0.6398(2) 0.0291(5) Uani 1 1 d . . .
C4A C 0.2411(2) 0.3932(2) 0.5946(2) 0.0253(5) Uani 1 1 d . . .
C5 C 0.1706(2) 0.4861(2) 0.5072(2) 0.0292(5) Uani 1 1 d . . .
H5 H 0.0885 0.4839 0.4788 0.035 Uiso 1 1 calc R U .
C6 C 0.2194(2) 0.5791(2) 0.4630(2) 0.0301(6) Uani 1 1 d . . .
H6 H 0.1712 0.6413 0.4044 0.036 Uiso 1 1 calc R U .
C7 C 0.3409(2) 0.5828(2) 0.5042(2) 0.0307(6) Uani 1 1 d . . .
H7 H 0.3743 0.6471 0.4723 0.037 Uiso 1 1 calc R U .
C8 C 0.4117(2) 0.4944(2) 0.5901(2) 0.0264(5) Uani 1 1 d . . .
H8 H 0.4936 0.4986 0.6176 0.032 Uiso 1 1 calc R U .
C8A C 0.3640(2) 0.3967(2) 0.6385(2) 0.0243(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'
F F 0.0171 0.0103 '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'
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_3
C2 C1 C8A 118.5(2) .
C2 C1 C1 119.76(18) 2_656
C8A C1 C1 121.67(17) 2_656
C1 C2 C3 122.1(2) .
C1 C2 H2 118.9 .
C3 C2 H2 118.9 .
C4 C3 C2 118.6(2) .
C4 C3 H3 120.7 .
C2 C3 H3 120.7 .
C3 C4 F1 120.2(3) .
C3 C4 C4A 123.5(2) .
F1 C4 C4A 116.3(3) .
C3 C4 Br1 111.1(2) .
F1 C4 Br1 11.6(3) .
C4A C4 Br1 124.9(2) .
C5 C4A C4 122.6(2) .
C5 C4A C8A 120.0(2) .
C4 C4A C8A 117.4(2) .
C6 C5 C4A 120.6(2) .
C6 C5 H5 119.7 .
C4A C5 H5 119.7 .
C5 C6 C7 120.1(2) .
C5 C6 H6 120.0 .
C7 C6 H6 120.0 .
C8 C7 C6 120.6(2) .
C8 C7 H7 119.7 .
C6 C7 H7 119.7 .
C7 C8 C8A 120.9(2) .
C7 C8 H8 119.6 .
C8A C8 H8 119.6 .
C4A C8A C8 117.9(2) .
C4A C8A C1 119.9(2) .
C8 C8A C1 122.2(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.762(5) .
F1 C4 1.404(5) .
C1 C2 1.378(3) .
C1 C8A 1.436(3) .
C1 C1 1.491(5) 2_656
C2 C3 1.404(4) .
C2 H2 0.9500 .
C3 C4 1.350(3) .
C3 H3 0.9500 .
C4 C4A 1.412(3) .
C4A C5 1.411(3) .
C4A C8A 1.418(3) .
C5 C6 1.367(3) .
C5 H5 0.9500 .
C6 C7 1.406(4) .
C6 H6 0.9500 .
C7 C8 1.372(3) .
C7 H7 0.9500 .
C8 C8A 1.421(3) .
C8 H8 0.9500 .
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
C8A C1 C2 C3 -2.1(3) .
C1 C1 C2 C3 179.7(2) 2_656
C1 C2 C3 C4 0.6(3) .
C2 C3 C4 F1 -179.2(3) .
C2 C3 C4 C4A 1.3(3) .
C2 C3 C4 Br1 -171.3(2) .
C3 C4 C4A C5 177.2(2) .
F1 C4 C4A C5 -2.2(4) .
Br1 C4 C4A C5 -11.1(4) .
C3 C4 C4A C8A -1.5(3) .
F1 C4 C4A C8A 179.0(3) .
Br1 C4 C4A C8A 170.1(2) .
C4 C4A C5 C6 -178.0(2) .
C8A C4A C5 C6 0.7(3) .
C4A C5 C6 C7 0.2(3) .
C5 C6 C7 C8 -0.8(3) .
C6 C7 C8 C8A 0.5(3) .
C5 C4A C8A C8 -0.9(3) .
C4 C4A C8A C8 177.83(19) .
C5 C4A C8A C1 -178.92(19) .
C4 C4A C8A C1 -0.2(3) .
C7 C8 C8A C4A 0.4(3) .
C7 C8 C8A C1 178.3(2) .
C2 C1 C8A C4A 1.9(3) .
C1 C1 C8A C4A -179.9(2) 2_656
C2 C1 C8A C8 -176.0(2) .
C1 C1 C8A C8 2.2(3) 2_656
