#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:35:36 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260619 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127153.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_7127153
loop_
_publ_author_name
'Škoch, Karel'
'Daniliuc, Constantin G.'
'Kehr, Gerald'
'Erker, Gerhard'
_publ_section_title
;
 Using the FpXylBH₂•SMe₂ reagent for the
 regioselective synthesis of cyclic bis(alkenyl)boranes.
;
_journal_issue                   81
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12178
_journal_page_last               12181
_journal_paper_doi               10.1039/d0cc05230b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C16 H10 B2 F12'
_chemical_formula_weight         451.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2020-07-16 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.564(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5560(3)
_cell_length_b                   8.4678(3)
_cell_length_c                   13.5930(5)
_cell_measurement_reflns_used    3836
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.7107
_cell_measurement_theta_min      6.5562
_cell_volume                     864.02(6)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11415
_diffrn_reflns_theta_full        66.78
_diffrn_reflns_theta_max         66.78
_diffrn_reflns_theta_min         6.17
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.737
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0438
_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)+(0.0455P)²+0.5399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                1264
_reflns_number_total             1519
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05230b2.cif
_cod_data_source_block           erk9658
_cod_depositor_comments
'Adding full bibliography for 7127153--7127160.cif.'
_cod_database_code               7127153
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.4182(3) 0.5250(3) 0.53926(17) 0.0181(5) Uani d . . . 1 . .
H H1 0.303(3) 0.586(3) 0.5065(16) 0.022(6) Uiso d . . . 1 . .
H H2 0.556(3) 0.590(2) 0.5149(15) 0.016(5) Uiso d . . . 1 . .
C C1 0.4435(3) 0.4787(2) 0.65292(14) 0.0160(4) Uani d . . . 1 . .
C C2 0.3032(3) 0.4176(2) 0.70116(14) 0.0172(4) Uani d . . . 1 . .
C C3 0.3252(3) 0.3813(2) 0.80163(14) 0.0197(5) Uani d . . . 1 . .
H H3 0.2286 0.3391 0.8322 0.024 Uiso calc U . R 1 . .
C C4 0.4879(3) 0.4067(2) 0.85680(14) 0.0208(5) Uani d . . . 1 . .
H H4 0.5034 0.3829 0.9256 0.025 Uiso calc U . R 1 . .
C C5 0.6284(3) 0.4671(2) 0.81120(14) 0.0168(4) Uani d . . . 1 . .
C C6 0.6064(3) 0.5019(2) 0.71030(14) 0.0171(4) Uani d . . . 1 . .
H H6 0.7044 0.5421 0.6801 0.021 Uiso calc U . R 1 . .
C C7 0.1245(3) 0.3907(2) 0.64326(15) 0.0196(5) Uani d . . . 1 . .
F F1 0.13841(17) 0.30897(15) 0.55925(9) 0.0266(3) Uani d . . . 1 . .
F F2 0.04002(16) 0.52605(14) 0.61574(9) 0.0234(3) Uani d . . . 1 . .
F F3 0.01305(17) 0.30839(15) 0.69379(9) 0.0273(3) Uani d . . . 1 . .
C C8 0.8026(3) 0.4955(2) 0.87285(15) 0.0208(5) Uani d . . . 1 . .
F F4 0.91489(18) 0.58457(16) 0.82772(9) 0.0318(4) Uani d . . . 1 . .
F F5 0.88899(17) 0.36021(15) 0.89748(10) 0.0312(3) Uani d . . . 1 . .
F F6 0.78091(19) 0.56824(19) 0.95824(9) 0.0404(4) Uani d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 B1 B1 . 3_666 120.9(2) ?
C1 B1 H1 . . 122.1(12) ?
B1 B1 H1 3_666 . 117.1(12) ?
C1 B1 H2 . . 110.7(10) ?
B1 B1 H2 3_666 . 44.6(10) ?
H1 B1 H2 . . 110.0(16) ?
C6 C1 C2 . . 117.07(18) ?
C6 C1 B1 . . 120.73(18) ?
C2 C1 B1 . . 122.17(18) ?
C3 C2 C1 . . 121.81(19) ?
C3 C2 C7 . . 118.72(18) ?
C1 C2 C7 . . 119.47(17) ?
C4 C3 C2 . . 119.82(19) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 119.59(18) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.44(19) ?
C4 C5 C8 . . 118.57(18) ?
C6 C5 C8 . . 120.99(19) ?
C5 C6 C1 . . 121.26(19) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
F3 C7 F2 . . 106.26(17) ?
F3 C7 F1 . . 106.33(16) ?
F2 C7 F1 . . 106.40(16) ?
F3 C7 C2 . . 112.97(16) ?
F2 C7 C2 . . 112.75(16) ?
F1 C7 C2 . . 111.64(17) ?
F4 C8 F6 . . 106.59(17) ?
F4 C8 F5 . . 106.26(18) ?
F6 C8 F5 . . 106.28(17) ?
F4 C8 C5 . . 113.45(16) ?
F6 C8 C5 . . 111.84(17) ?
F5 C8 C5 . . 111.94(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 C1 . 1.584(3) ?
B1 B1 3_666 1.774(5) ?
B1 H1 . 1.06(2) ?
B1 H2 . 1.25(2) ?
C1 C6 . 1.394(3) ?
C1 C2 . 1.407(3) ?
C2 C3 . 1.391(3) ?
C2 C7 . 1.501(3) ?
C3 C4 . 1.382(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.387(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.394(3) ?
C5 C8 . 1.497(3) ?
C6 H6 . 0.95 ?
C7 F3 . 1.341(2) ?
C7 F2 . 1.344(2) ?
C7 F1 . 1.350(2) ?
C8 F4 . 1.335(3) ?
C8 F6 . 1.340(2) ?
C8 F5 . 1.342(2) ?
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
B1 B1 C1 C6 3_666 . . . 44.8(3) ?
B1 B1 C1 C2 3_666 . . . -137.2(2) ?
C6 C1 C2 C3 . . . . -0.1(3) ?
B1 C1 C2 C3 . . . . -178.19(19) ?
C6 C1 C2 C7 . . . . 179.76(17) ?
B1 C1 C2 C7 . . . . 1.7(3) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C7 C2 C3 C4 . . . . -179.25(18) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C3 C4 C5 C8 . . . . 179.21(18) ?
C4 C5 C6 C1 . . . . 0.7(3) ?
C8 C5 C6 C1 . . . . -178.66(18) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
B1 C1 C6 C5 . . . . 177.57(19) ?
C3 C2 C7 F3 . . . . -10.6(3) ?
C1 C2 C7 F3 . . . . 169.51(17) ?
C3 C2 C7 F2 . . . . 109.9(2) ?
C1 C2 C7 F2 . . . . -70.0(2) ?
C3 C2 C7 F1 . . . . -130.37(19) ?
C1 C2 C7 F1 . . . . 49.7(2) ?
C4 C5 C8 F4 . . . . -166.12(18) ?
C6 C5 C8 F4 . . . . 13.2(3) ?
C4 C5 C8 F6 . . . . -45.5(3) ?
C6 C5 C8 F6 . . . . 133.8(2) ?
C4 C5 C8 F5 . . . . 73.6(2) ?
C6 C5 C8 F5 . . . . -107.0(2) ?
