#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/65/7056566.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_7056566
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            'C40 H24 Br0.55 F3.45'
_chemical_formula_weight         614.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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            2
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0263
_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            10738
_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    0.901
_exptl_absorpt_correction_T_max  0.94
_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    1.493
_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         0.177
_refine_diff_density_min         -0.152
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.47(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0344
_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)+(0.0358P)²+0.6309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0815
_reflns_number_gt                2359
_reflns_number_total             2812
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj02299a2.cif
_cod_data_source_block           10-1_in_C2
_cod_database_code               7056566
#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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
Br Br1A 0.4526(5) 0.4689(7) 0.1324(6) 0.0289(10) Uani d . P . 0.194(3)
F F1A 0.4288(6) 0.4591(10) 0.1527(7) 0.036(2) Uani d . P . 0.806(3)
C C1A 0.0655(3) 0.4488(4) 0.0247(3) 0.0258(9) Uani d . . . 1.0
C C2A 0.1182(3) 0.5453(4) -0.0126(3) 0.0301(9) Uani d . . . 1.0
H H2A 0.0712 0.6101 -0.0681 0.036 Uiso calc U . R 1.0
C C3A 0.2390(3) 0.5495(4) 0.0296(3) 0.0317(9) Uani d . . . 1.0
H H3A 0.2738 0.6164 0.0029 0.038 Uiso calc U . R 1.0
C C4A 0.3058(3) 0.4578(5) 0.1084(3) 0.0305(8) Uani d . . . 1.0
C C4AA 0.2591(3) 0.3580(4) 0.1551(3) 0.0270(9) Uani d . . . 1.0
C C5A 0.3303(4) 0.2654(4) 0.2421(4) 0.0290(10) Uani d . . . 1.0
H H5A 0.4123 0.2666 0.2691 0.035 Uiso calc U . R 1.0
C C6A 0.2812(4) 0.1742(4) 0.2870(4) 0.0339(10) Uani d . . . 1.0
H H6A 0.3299 0.1129 0.3466 0.041 Uiso calc U . R 1.0
C C7A 0.1614(5) 0.1685(4) 0.2479(5) 0.0336(11) Uani d . . . 1.0
H H7A 0.129 0.1043 0.2811 0.04 Uiso calc U . R 1.0
C C8A 0.0895(3) 0.2564(4) 0.1604(3) 0.0296(9) Uani d . . . 1.0
H H8A 0.0075 0.2511 0.1326 0.035 Uiso calc U . R 1.0
C C8AA 0.1362(3) 0.3552(3) 0.1113(3) 0.0249(9) Uani d . . . 1.0
Br Br1B 0.0499(9) 0.5346(13) 0.3685(11) 0.021(2) Uani d . P D 0.081(3)
F F1B 0.0748(4) 0.5450(7) 0.3470(5) 0.0308(13) Uani d . P . 0.919(3)
C C1B 0.4358(3) 0.5504(4) 0.4756(3) 0.0259(8) Uani d . . . 1.0
C C2B 0.3809(3) 0.4558(4) 0.5102(3) 0.0281(9) Uani d . . . 1.0
H H2B 0.4272 0.3907 0.5656 0.034 Uiso calc U . R 1.0
C C3B 0.2595(3) 0.4504(4) 0.4677(3) 0.0297(9) Uani d . . . 1.0
H H3B 0.2241 0.3836 0.4937 0.036 Uiso calc U . R 1.0
C C4B 0.1942(3) 0.5445(4) 0.3881(3) 0.0277(8) Uani d . . D 1.0
C C4AB 0.2416(3) 0.6442(4) 0.3445(3) 0.0253(9) Uani d . . . 1.0
C C5B 0.1718(4) 0.7383(4) 0.2563(4) 0.0292(10) Uani d . . . 1.0
H H5B 0.0895 0.736 0.2267 0.035 Uiso calc U . R 1.0
C C6B 0.2208(3) 0.8322(4) 0.2130(4) 0.0279(9) Uani d . . . 1.0
H H6B 0.1735 0.8954 0.1549 0.034 Uiso calc U . R 1.0
C C7B 0.3430(4) 0.8333(4) 0.2564(5) 0.0294(10) Uani d . . . 1.0
H H7B 0.3777 0.8976 0.2261 0.035 Uiso calc U . R 1.0
C C8B 0.4122(3) 0.7450(4) 0.3401(3) 0.0256(8) Uani d . . . 1.0
H H8B 0.4942 0.7484 0.3672 0.031 Uiso calc U . R 1.0
C C8AB 0.3643(3) 0.6477(3) 0.3880(3) 0.0253(9) Uani d . . . 1.0
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_site_symmetry_3
_geom_angle
C2A C1A C8AA . 119.0(3)
C2A C1A C1A 2 119.0(3)
C8AA C1A C1A 2 121.9(3)
C1A C2A C3A . 121.4(4)
C1A C2A H2A . 119.3
C3A C2A H2A . 119.3
C4A C3A C2A . 119.4(4)
C4A C3A H3A . 120.3
C2A C3A H3A . 120.3
C3A C4A C4AA . 122.7(3)
C3A C4A F1A . 120.8(5)
C4AA C4A F1A . 116.4(5)
C3A C4A Br1A . 112.2(4)
C4AA C4A Br1A . 124.8(4)
F1A C4A Br1A . 11.0(4)
C5A C4AA C8AA . 120.7(3)
C5A C4AA C4A . 122.2(4)
C8AA C4AA C4A . 117.1(3)
C6A C5A C4AA . 119.7(4)
C6A C5A H5A . 120.1
C4AA C5A H5A . 120.1
C5A C6A C7A . 121.6(4)
C5A C6A H6A . 119.2
C7A C6A H6A . 119.2
C8A C7A C6A . 119.7(4)
C8A C7A H7A . 120.1
C6A C7A H7A . 120.1
C7A C8A C8AA . 121.2(4)
C7A C8A H8A . 119.4
C8AA C8A H8A . 119.4
C1A C8AA C4AA . 120.3(3)
C1A C8AA C8A . 122.6(3)
C4AA C8AA C8A . 117.1(3)
C2B C1B C8AB . 118.1(3)
C2B C1B C1B 2_656 120.4(3)
C8AB C1B C1B 2_656 121.5(3)
C1B C2B C3B . 123.3(4)
C1B C2B H2B . 118.4
C3B C2B H2B . 118.4
C4B C3B C2B . 117.7(4)
C4B C3B H3B . 121.2
C2B C3B H3B . 121.2
C3B C4B F1B . 119.7(4)
C3B C4B C4AB . 123.6(3)
F1B C4B C4AB . 116.7(4)
C3B C4B Br1B . 110.4(5)
F1B C4B Br1B . 11.6(5)
C4AB C4B Br1B . 125.4(5)
C4B C4AB C8AB . 117.9(3)
C4B C4AB C5B . 122.9(4)
C8AB C4AB C5B . 119.2(3)
C6B C5B C4AB . 121.3(4)
C6B C5B H5B . 119.3
C4AB C5B H5B . 119.3
C5B C6B C7B . 118.6(4)
C5B C6B H6B . 120.7
C7B C6B H6B . 120.7
C8B C7B C6B . 121.7(4)
C8B C7B H7B . 119.1
C6B C7B H7B . 119.1
C7B C8B C8AB . 121.0(3)
C7B C8B H8B . 119.5
C8AB C8B H8B . 119.5
C8B C8AB C4AB . 118.2(3)
C8B C8AB C1B . 122.3(3)
C4AB C8AB C1B . 119.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1A C4A . 1.765(6)
F1A C4A . 1.420(8)
C1A C2A . 1.382(5)
C1A C8AA . 1.414(5)
C1A C1A 2 1.510(7)
C2A C3A . 1.398(5)
C2A H2A . 0.95
C3A C4A . 1.347(6)
C3A H3A . 0.95
C4A C4AA . 1.420(5)
C4AA C5A . 1.411(6)
C4AA C8AA . 1.419(5)
C5A C6A . 1.360(6)
C5A H5A . 0.95
C6A C7A . 1.390(6)
C6A H6A . 0.95
C7A C8A . 1.381(6)
C7A H7A . 0.95
C8A C8AA . 1.427(5)
C8A H8A . 0.95
Br1B C4B . 1.748(9)
F1B C4B . 1.380(6)
C1B C2B . 1.370(6)
C1B C8AB . 1.450(5)
C1B C1B 2_656 1.478(7)
C2B C3B . 1.403(5)
C2B H2B . 0.95
C3B C4B . 1.363(5)
C3B H3B . 0.95
C4B C4AB . 1.404(5)
C4AB C8AB . 1.418(5)
C4AB C5B . 1.421(6)
C5B C6B . 1.370(6)
C5B H5B . 0.95
C6B C7B . 1.411(6)
C6B H6B . 0.95
C7B C8B . 1.354(6)
C7B H7B . 0.95
C8B C8AB . 1.416(5)
C8B H8B . 0.95
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_site_symmetry_1
_geom_torsion
C8AA C1A C2A C3A . 2.3(5)
C1A C1A C2A C3A 2 -179.6(3)
C1A C2A C3A C4A . -0.1(5)
C2A C3A C4A C4AA . -2.3(5)
C2A C3A C4A F1A . 179.8(5)
C2A C3A C4A Br1A . 172.1(4)
C3A C4A C4AA C5A . -177.3(4)
F1A C4A C4AA C5A . 0.7(6)
Br1A C4A C4AA C5A . 9.0(6)
C3A C4A C4AA C8AA . 2.2(5)
F1A C4A C4AA C8AA . -179.7(5)
Br1A C4A C4AA C8AA . -171.4(4)
C8AA C4AA C5A C6A . -1.7(6)
C4A C4AA C5A C6A . 177.9(3)
C4AA C5A C6A C7A . 1.0(6)
C5A C6A C7A C8A . 0.5(6)
C6A C7A C8A C8AA . -1.3(6)
C2A C1A C8AA C4AA . -2.3(5)
C1A C1A C8AA C4AA 2 179.7(3)
C2A C1A C8AA C8A . 176.4(3)
C1A C1A C8AA C8A 2 -1.6(5)
C5A C4AA C8AA C1A . 179.7(4)
C4A C4AA C8AA C1A . 0.1(5)
C5A C4AA C8AA C8A . 0.9(5)
C4A C4AA C8AA C8A . -178.7(3)
C7A C8A C8AA C1A . -178.1(4)
C7A C8A C8AA C4AA . 0.6(5)
C8AB C1B C2B C3B . -1.7(5)
C1B C1B C2B C3B 2_656 179.8(3)
C1B C2B C3B C4B . 0.1(5)
C2B C3B C4B F1B . -178.1(4)
C2B C3B C4B C4AB . 1.4(5)
C2B C3B C4B Br1B . -170.4(5)
C3B C4B C4AB C8AB . -1.2(5)
F1B C4B C4AB C8AB . 178.4(4)
Br1B C4B C4AB C8AB . 169.3(5)
C3B C4B C4AB C5B . 176.9(4)
F1B C4B C4AB C5B . -3.6(6)
Br1B C4B C4AB C5B . -12.6(7)
C4B C4AB C5B C6B . -178.2(3)
C8AB C4AB C5B C6B . -0.2(6)
C4AB C5B C6B C7B . 0.8(5)
C5B C6B C7B C8B . -0.7(5)
C6B C7B C8B C8AB . -0.2(6)
C7B C8B C8AB C4AB . 0.8(5)
C7B C8B C8AB C1B . 178.7(4)
C4B C4AB C8AB C8B . 177.4(3)
C5B C4AB C8AB C8B . -0.7(5)
C4B C4AB C8AB C1B . -0.5(5)
C5B C4AB C8AB C1B . -178.6(4)
C2B C1B C8AB C8B . -176.0(3)
C1B C1B C8AB C8B 2_656 2.5(5)
C2B C1B C8AB C4AB . 1.8(5)
C1B C1B C8AB C4AB 2_656 -179.6(3)
