#------------------------------------------------------------------------------
#$Date: 2019-11-23 16:23:06 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/45/7124594.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_7124594
loop_
_publ_author_name
'Légaré, Marc-André'
'Rochette, Étienne'
'Légaré Lavergne, Julien'
'Bouchard, Nicolas'
'Fontaine, Frédéric-Georges'
_publ_section_title
;
 Bench-stable frustrated Lewis pair chemistry: fluoroborate salts as
 precatalysts for the C-H borylation of heteroarenes.
;
_journal_issue                   31
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5387
_journal_page_last               5390
_journal_paper_doi               10.1039/c6cc01267a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C15 H23 B F3 N'
_chemical_formula_weight         285.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-12-04 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.5310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8666(9)
_cell_length_b                   7.6330(5)
_cell_length_c                   14.4543(9)
_cell_measurement_reflns_used    4538
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.0895
_cell_measurement_theta_min      2.8237
_cell_volume                     1480.06(16)
_computing_cell_refinement       APEX2
_computing_data_collection       APEX2
_computing_data_reduction        Saint
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20569
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.283
_diffrn_reflns_theta_min         1.518
_diffrn_source                   'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         5400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0442
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3950
_reflns_number_total             5400
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc01267a2.cif
_cod_data_source_block           ER1007_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7124594
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F3 F 0.14404(5) 0.65328(9) 0.56514(5) 0.02535(16) Uani 1 1 d . .
F1 F 0.17822(5) 0.59542(10) 0.42784(5) 0.02969(18) Uani 1 1 d . .
F2 F 0.26211(6) 0.81226(9) 0.54014(6) 0.03206(18) Uani 1 1 d . .
N1 N 0.22033(6) 0.38050(10) 0.69342(6) 0.01367(16) Uani 1 1 d . .
C1 C 0.30871(7) 0.50424(12) 0.59806(7) 0.01532(18) Uani 1 1 d . .
C2 C 0.30825(7) 0.38136(13) 0.66960(7) 0.01578(18) Uani 1 1 d . .
C6 C 0.39369(8) 0.50305(14) 0.57883(8) 0.0200(2) Uani 1 1 d . .
H6 H 0.3973 0.5842 0.5307 0.024 Uiso 1 1 calc R U
C7 C 0.14755(8) 0.22178(13) 0.64885(8) 0.0201(2) Uani 1 1 d . .
C13 C 0.24059(7) 0.44843(13) 0.80301(7) 0.01586(18) Uani 1 1 d . .
C12 C 0.13784(7) 0.48350(13) 0.79931(8) 0.0188(2) Uani 1 1 d . .
H12A H 0.1464 0.5196 0.8684 0.023 Uiso 1 1 calc R U
H12B H 0.1066 0.5824 0.7519 0.023 Uiso 1 1 calc R U
C5 C 0.47223(8) 0.38857(17) 0.62712(9) 0.0260(2) Uani 1 1 d . .
H5 H 0.5284 0.3918 0.6120 0.031 Uiso 1 1 calc R U
C11 C 0.06793(8) 0.32694(14) 0.76483(8) 0.0224(2) Uani 1 1 d . .
H11A H 0.0032 0.3582 0.7645 0.027 Uiso 1 1 calc R U
H11B H 0.0969 0.2284 0.8132 0.027 Uiso 1 1 calc R U
C3 C 0.38631(8) 0.26470(15) 0.71892(9) 0.0255(2) Uani 1 1 d . .
H3 H 0.3832 0.1825 0.7668 0.031 Uiso 1 1 calc R U
C14 C 0.29716(9) 0.62096(15) 0.81808(8) 0.0248(2) Uani 1 1 d . .
H14A H 0.2969 0.6831 0.8773 0.037 Uiso 1 1 calc R U
H14B H 0.2648 0.6936 0.7566 0.037 Uiso 1 1 calc R U
H14C H 0.3661 0.5969 0.8300 0.037 Uiso 1 1 calc R U
C15 C 0.30141(8) 0.32519(16) 0.89065(8) 0.0257(2) Uani 1 1 d . .
H15A H 0.3644 0.2973 0.8876 0.039 Uiso 1 1 calc R U
H15B H 0.2637 0.2170 0.8845 0.039 Uiso 1 1 calc R U
H15C H 0.3152 0.3819 0.9562 0.039 Uiso 1 1 calc R U
C10 C 0.05201(8) 0.27179(16) 0.65749(8) 0.0237(2) Uani 1 1 d . .
H10A H 0.0195 0.3693 0.6095 0.028 Uiso 1 1 calc R U
H10B H 0.0059 0.1706 0.6358 0.028 Uiso 1 1 calc R U
C8 C 0.12548(10) 0.20866(16) 0.53554(9) 0.0292(3) Uani 1 1 d . .
H8A H 0.1862 0.1741 0.5294 0.044 Uiso 1 1 calc R U
H8B H 0.1027 0.3227 0.5025 0.044 Uiso 1 1 calc R U
H8C H 0.0734 0.1208 0.5020 0.044 Uiso 1 1 calc R U
C4 C 0.46877(9) 0.26942(17) 0.69747(10) 0.0309(3) Uani 1 1 d . .
H4 H 0.5227 0.1909 0.7311 0.037 Uiso 1 1 calc R U
C9 C 0.18981(11) 0.04776(15) 0.70092(10) 0.0311(3) Uani 1 1 d . .
H9A H 0.2002 0.0525 0.7726 0.047 Uiso 1 1 calc R U
H9B H 0.2536 0.0253 0.6983 0.047 Uiso 1 1 calc R U
H9C H 0.1429 -0.0466 0.6654 0.047 Uiso 1 1 calc R U
B1 B 0.22217(9) 0.64447(15) 0.53179(9) 0.0191(2) Uani 1 1 d . .
H1 H 0.1839(10) 0.4730(17) 0.6540(11) 0.021(3) Uiso 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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C7 115.35(7)
C2 N1 C13 115.27(7)
C7 N1 C13 117.99(7)
C2 N1 H1 101.2(8)
C7 N1 H1 102.7(8)
C13 N1 H1 100.2(8)
C2 C1 C6 115.67(9)
C2 C1 B1 128.39(8)
C6 C1 B1 115.91(8)
C3 C2 C1 122.66(9)
C3 C2 N1 120.03(8)
C1 C2 N1 117.30(8)
C5 C6 C1 122.66(9)
C5 C6 H6 118.7
C1 C6 H6 118.7
C9 C7 C10 112.20(9)
C9 C7 C8 108.95(9)
C10 C7 C8 109.04(9)
C9 C7 N1 114.01(9)
C10 C7 N1 105.97(8)
C8 C7 N1 106.41(8)
C15 C13 C14 108.72(9)
C15 C13 C12 111.30(8)
C14 C13 C12 109.55(8)
C15 C13 N1 115.01(8)
C14 C13 N1 106.48(7)
C12 C13 N1 105.58(7)
C11 C12 C13 113.92(8)
C11 C12 H12A 108.8
C13 C12 H12A 108.8
C11 C12 H12B 108.8
C13 C12 H12B 108.8
H12A C12 H12B 107.7
C4 C5 C6 119.76(10)
C4 C5 H5 120.1
C6 C5 H5 120.1
C12 C11 C10 109.58(8)
C12 C11 H11A 109.8
C10 C11 H11A 109.8
C12 C11 H11B 109.8
C10 C11 H11B 109.8
H11A C11 H11B 108.2
C4 C3 C2 119.39(10)
C4 C3 H3 120.3
C2 C3 H3 120.3
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C11 C10 C7 114.23(9)
C11 C10 H10A 108.7
C7 C10 H10A 108.7
C11 C10 H10B 108.7
C7 C10 H10B 108.7
H10A C10 H10B 107.6
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C5 C4 C3 119.87(10)
C5 C4 H4 120.1
C3 C4 H4 120.1
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
F2 B1 F1 108.74(8)
F2 B1 F3 107.65(8)
F1 B1 F3 107.46(9)
F2 B1 C1 110.70(9)
F1 B1 C1 109.79(8)
F3 B1 C1 112.37(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F3 B1 1.4383(12)
F1 B1 1.4066(13)
F2 B1 1.3949(13)
N1 C2 1.4883(11)
N1 C7 1.5661(13)
N1 C13 1.5676(12)
N1 H1 0.922(14)
C1 C2 1.3982(13)
C1 C6 1.4059(13)
C1 B1 1.6298(15)
C2 C3 1.3909(14)
C6 C5 1.3826(16)
C6 H6 0.9500
C7 C9 1.5224(16)
C7 C10 1.5270(15)
C7 C8 1.5288(15)
C13 C15 1.5231(14)
C13 C14 1.5268(14)
C13 C12 1.5289(13)
C12 C11 1.5199(14)
C12 H12A 0.9900
C12 H12B 0.9900
C5 C4 1.3817(17)
C5 H5 0.9500
C11 C10 1.5244(15)
C11 H11A 0.9900
C11 H11B 0.9900
C3 C4 1.3885(15)
C3 H3 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C10 H10A 0.9900
C10 H10B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C4 H4 0.9500
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
