#------------------------------------------------------------------------------
#$Date: 2024-05-05 05:36:31 +0300 (Sun, 05 May 2024) $
#$Revision: 291606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/54/7715434.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_7715434
loop_
_publ_author_name
'Nguyen, Tony'
'Dutton, Jason L.'
'Chang, Chia Yun'
'Zhou, Wen'
'Piers, Warren E.'
_publ_section_title
;
 Direct C-H electrophilic borylation with
 (C₆F₅)₂B-NTf₂ to generate B-N
 dibenzo[a,h]pyrenes.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7273
_journal_page_last               7281
_journal_paper_doi               10.1039/d4dt00469h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'B C13 F13 O3 S'
_chemical_formula_sum            'C13 B F13 O3 S'
_chemical_formula_weight         494.00
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.0522(15)
_cell_length_b                   11.2332(6)
_cell_length_c                   8.4733(4)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      2.67
_cell_volume                     3146.0(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17899
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.679
_diffrn_reflns_theta_max         66.679
_diffrn_reflns_theta_min         2.674
_diffrn_source_current           0.64
_diffrn_source_power             0.0285952
_diffrn_source_voltage           44.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.450
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1360 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.5747.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_description       plank
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.567
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0324
_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)+(0.0476P)²+1.9080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2548
_reflns_number_total             2781
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00469h2.cif
_cod_data_source_block           tn02_154
_cod_depositor_comments
'Adding full bibliography for 7715430--7715439.cif.'
_cod_database_code               7715434
_shelx_shelxl_version_number     2018/3
_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_max   0.742
_shelx_estimated_absorpt_t_min   0.245
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id TN02-154
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
S1 S 0.61118(2) 0.39930(4) 0.38741(6) 0.02674(15) Uani 1 1 d . . . . .
F5 F 0.66285(3) 0.84382(10) 0.20215(14) 0.0315(3) Uani 1 1 d . . . . .
F10 F 0.68540(3) 0.45021(10) 0.23282(13) 0.0324(3) Uani 1 1 d . . . . .
F6 F 0.68334(3) 0.80725(10) 0.52781(14) 0.0333(3) Uani 1 1 d . . . . .
F1 F 0.55057(3) 0.68357(10) 0.47500(15) 0.0356(3) Uani 1 1 d . . . . .
F7 F 0.76378(4) 0.80642(11) 0.53307(14) 0.0393(3) Uani 1 1 d . . . . .
F9 F 0.76526(4) 0.44871(11) 0.24599(14) 0.0395(3) Uani 1 1 d . . . . .
F2 F 0.51017(3) 0.88490(11) 0.42518(16) 0.0397(3) Uani 1 1 d . . . . .
F4 F 0.62152(4) 1.04414(11) 0.15317(17) 0.0425(3) Uani 1 1 d . . . . .
F3 F 0.54519(4) 1.06680(11) 0.26465(17) 0.0442(3) Uani 1 1 d . . . . .
F8 F 0.80569(3) 0.62775(13) 0.39249(15) 0.0438(3) Uani 1 1 d . . . . .
F11 F 0.55289(4) 0.43937(12) 0.58993(15) 0.0428(3) Uani 1 1 d . . . . .
O1 O 0.60781(4) 0.53600(11) 0.35649(16) 0.0271(3) Uani 1 1 d . . . . .
F12 F 0.53286(4) 0.40736(14) 0.35369(16) 0.0527(4) Uani 1 1 d . . . . .
F13 F 0.55582(4) 0.26314(12) 0.49503(18) 0.0543(4) Uani 1 1 d . . . . .
O2 O 0.63795(4) 0.37549(13) 0.51402(18) 0.0349(3) Uani 1 1 d . . . . .
O3 O 0.61310(4) 0.33767(14) 0.24251(19) 0.0403(4) Uani 1 1 d . . . . .
C6 C 0.62552(5) 0.85121(17) 0.2620(2) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.68002(5) 0.62812(16) 0.3806(2) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.60918(5) 0.75469(17) 0.3429(2) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.56954(5) 0.77065(17) 0.3962(2) 0.0255(4) Uani 1 1 d . . . . .
C8 C 0.70232(5) 0.71741(16) 0.4552(2) 0.0246(4) Uani 1 1 d . . . . .
C12 C 0.70337(5) 0.53866(16) 0.3126(2) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.74391(6) 0.71788(17) 0.4605(2) 0.0273(4) Uani 1 1 d . . . . .
C5 C 0.60477(6) 0.95525(17) 0.2345(2) 0.0292(4) Uani 1 1 d . . . . .
C3 C 0.54823(5) 0.87439(18) 0.3723(2) 0.0287(4) Uani 1 1 d . . . . .
C11 C 0.74487(6) 0.53698(17) 0.3163(2) 0.0272(4) Uani 1 1 d . . . . .
C4 C 0.56575(6) 0.96675(17) 0.2908(2) 0.0308(4) Uani 1 1 d . . . . .
C10 C 0.76547(6) 0.62715(19) 0.3901(2) 0.0288(4) Uani 1 1 d . . . . .
C13 C 0.55935(6) 0.37772(19) 0.4610(2) 0.0334(5) Uani 1 1 d . . . . .
B B 0.63299(6) 0.63567(19) 0.3634(2) 0.0230(4) 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
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 2.00 1.00 0.1270
-1.00 1.00 0.00 0.0390
1.00 1.00 0.00 0.0480
-1.00 -1.00 0.00 0.0210
-1.00 0.00 0.00 0.0240
1.00 0.00 0.00 0.0520
2.00 1.00 -1.00 0.2400
-1.00 -1.00 1.00 0.2030
-1.00 2.00 -1.00 0.1670
-1.00 -1.00 -1.00 0.1980
0.00 -1.00 0.00 0.0260
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
O1 S1 C13 96.89(8) . . ?
O2 S1 O1 110.94(8) . . ?
O2 S1 C13 107.48(9) . . ?
O3 S1 O1 109.86(9) . . ?
O3 S1 O2 122.57(10) . . ?
O3 S1 C13 105.79(9) . . ?
B O1 S1 137.63(12) . . ?
F5 C6 C1 119.79(16) . . ?
F5 C6 C5 116.67(16) . . ?
C5 C6 C1 123.51(17) . . ?
C8 C7 B 121.88(16) . . ?
C12 C7 C8 114.42(16) . . ?
C12 C7 B 123.49(16) . . ?
C6 C1 C2 115.04(17) . . ?
C6 C1 B 121.74(16) . . ?
C2 C1 B 123.14(17) . . ?
F1 C2 C1 120.40(17) . . ?
F1 C2 C3 116.87(16) . . ?
C3 C2 C1 122.73(18) . . ?
F6 C8 C7 120.16(16) . . ?
F6 C8 C9 116.79(16) . . ?
C9 C8 C7 123.04(17) . . ?
F10 C12 C7 119.88(16) . . ?
F10 C12 C11 116.38(16) . . ?
C11 C12 C7 123.69(17) . . ?
F7 C9 C8 120.48(17) . . ?
F7 C9 C10 119.56(17) . . ?
C8 C9 C10 119.96(17) . . ?
F4 C5 C6 121.13(18) . . ?
F4 C5 C4 119.76(17) . . ?
C6 C5 C4 119.11(17) . . ?
F2 C3 C2 120.36(18) . . ?
F2 C3 C4 119.78(17) . . ?
C4 C3 C2 119.84(18) . . ?
F9 C11 C12 120.21(17) . . ?
F9 C11 C10 120.00(17) . . ?
C10 C11 C12 119.79(17) . . ?
F3 C4 C5 119.84(18) . . ?
F3 C4 C3 120.39(18) . . ?
C3 C4 C5 119.77(17) . . ?
F8 C10 C9 120.42(18) . . ?
F8 C10 C11 120.47(18) . . ?
C11 C10 C9 119.11(17) . . ?
F11 C13 S1 111.37(13) . . ?
F11 C13 F13 108.49(17) . . ?
F12 C13 S1 110.81(14) . . ?
F12 C13 F11 109.66(18) . . ?
F12 C13 F13 109.92(17) . . ?
F13 C13 S1 106.51(15) . . ?
O1 B C7 123.58(17) . . ?
O1 B C1 112.43(15) . . ?
C1 B C7 123.92(16) . . ?
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
S1 O1 1.5618(13) . ?
S1 O2 1.4162(14) . ?
S1 O3 1.4110(15) . ?
S1 C13 1.839(2) . ?
F5 C6 1.336(2) . ?
F10 C12 1.340(2) . ?
F6 C8 1.338(2) . ?
F1 C2 1.340(2) . ?
F7 C9 1.341(2) . ?
F9 C11 1.339(2) . ?
F2 C3 1.341(2) . ?
F4 C5 1.333(2) . ?
F3 C4 1.332(2) . ?
F8 C10 1.330(2) . ?
F11 C13 1.311(3) . ?
O1 B 1.396(2) . ?
F12 C13 1.305(2) . ?
F13 C13 1.324(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.375(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.392(3) . ?
C7 B 1.564(3) . ?
C1 C2 1.397(3) . ?
C1 B 1.561(3) . ?
C2 C3 1.377(3) . ?
C8 C9 1.375(3) . ?
C12 C11 1.372(3) . ?
C9 C10 1.379(3) . ?
C5 C4 1.381(3) . ?
C3 C4 1.374(3) . ?
C11 C10 1.371(3) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 O1 B C7 12.3(3) . . . . ?
S1 O1 B C1 -170.75(14) . . . . ?
F5 C6 C1 C2 -178.10(16) . . . . ?
F5 C6 C1 B -1.3(3) . . . . ?
F5 C6 C5 F4 -0.6(3) . . . . ?
F5 C6 C5 C4 178.68(17) . . . . ?
F10 C12 C11 F9 -1.6(3) . . . . ?
F10 C12 C11 C10 177.35(17) . . . . ?
F6 C8 C9 F7 -1.3(3) . . . . ?
F6 C8 C9 C10 179.11(17) . . . . ?
F1 C2 C3 F2 -0.7(3) . . . . ?
F1 C2 C3 C4 -179.26(17) . . . . ?
F7 C9 C10 F8 -0.7(3) . . . . ?
F7 C9 C10 C11 179.98(17) . . . . ?
F9 C11 C10 F8 0.0(3) . . . . ?
F9 C11 C10 C9 179.36(17) . . . . ?
F2 C3 C4 F3 0.3(3) . . . . ?
F2 C3 C4 C5 -179.08(18) . . . . ?
F4 C5 C4 F3 -0.5(3) . . . . ?
F4 C5 C4 C3 178.91(18) . . . . ?
O1 S1 C13 F11 -61.94(15) . . . . ?
O1 S1 C13 F12 60.42(16) . . . . ?
O1 S1 C13 F13 179.94(14) . . . . ?
O2 S1 O1 B 34.8(2) . . . . ?
O2 S1 C13 F11 52.60(17) . . . . ?
O2 S1 C13 F12 174.96(15) . . . . ?
O2 S1 C13 F13 -65.51(16) . . . . ?
O3 S1 O1 B -103.9(2) . . . . ?
O3 S1 C13 F11 -174.89(14) . . . . ?
O3 S1 C13 F12 -52.53(18) . . . . ?
O3 S1 C13 F13 67.00(16) . . . . ?
C6 C1 C2 F1 179.68(16) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C1 B O1 -143.84(17) . . . . ?
C6 C1 B C7 33.1(3) . . . . ?
C6 C5 C4 F3 -179.76(18) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C7 C8 C9 F7 179.55(17) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C12 C11 F9 -178.94(17) . . . . ?
C7 C12 C11 C10 0.0(3) . . . . ?
C1 C6 C5 F4 -178.49(17) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C1 C2 C3 F2 179.62(17) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C1 B O1 32.7(3) . . . . ?
C2 C1 B C7 -150.33(18) . . . . ?
C2 C3 C4 F3 178.87(17) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C8 C7 C12 F10 -177.71(16) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C7 B O1 -150.77(18) . . . . ?
C8 C7 B C1 32.6(3) . . . . ?
C8 C9 C10 F8 178.95(18) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C12 C7 C8 F6 -178.70(16) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C12 C7 B O1 34.8(3) . . . . ?
C12 C7 B C1 -141.83(19) . . . . ?
C12 C11 C10 F8 -178.90(17) . . . . ?
C12 C11 C10 C9 0.4(3) . . . . ?
C5 C6 C1 C2 -0.3(3) . . . . ?
C5 C6 C1 B 176.55(18) . . . . ?
C13 S1 O1 B 146.6(2) . . . . ?
B C7 C8 F6 6.4(3) . . . . ?
B C7 C8 C9 -174.45(18) . . . . ?
B C7 C12 F10 -2.9(3) . . . . ?
B C7 C12 C11 174.41(18) . . . . ?
B C1 C2 F1 2.9(3) . . . . ?
B C1 C2 C3 -177.43(18) . . . . ?
