# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_140501LT_a
_database_code_depnum_ccdc_archive 'CCDC 1495726'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2017-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 B F4 N'
_chemical_formula_weight         333.13

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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'

_cell_length_a                   20.2206(11)
_cell_length_b                   9.2842(5)
_cell_length_c                   8.5994(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1614.38(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Lump
_exptl_crystal_colour            'Yellow Brown'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8438
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12010
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3276
_reflns_number_gt                2384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0789P)²+0.3203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3276
_refine_ls_number_parameters     264
_refine_ls_number_restraints     187
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
C1 C 0.56416(16) 0.7172(4) 0.7266(4) 0.0385(8) Uani 1 1 d . . . . .
C2 C 0.56406(16) 0.7824(4) 0.5763(4) 0.0390(8) Uani 1 1 d . . . . .
C3 C 0.50628(18) 0.8129(4) 0.4898(5) 0.0475(10) Uani 1 1 d . . . . .
H3 H 0.4650 0.7898 0.5303 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5108(2) 0.8758(5) 0.3480(5) 0.0583(11) Uani 1 1 d . . . . .
H4 H 0.4722 0.8970 0.2940 0.070 Uiso 1 1 calc R U . . .
C5 C 0.5721(2) 0.9101(5) 0.2799(5) 0.0614(12) Uani 1 1 d . . . . .
H5 H 0.5737 0.9524 0.1819 0.074 Uiso 1 1 calc R U . . .
C6 C 0.6284(2) 0.8813(5) 0.3578(5) 0.0561(11) Uani 1 1 d . . . . .
H6 H 0.6690 0.9032 0.3129 0.067 Uiso 1 1 calc R U . . .
C7 C 0.62612(17) 0.8182(4) 0.5068(5) 0.0437(9) Uani 1 1 d . . . . .
C8 C 0.68406(18) 0.7911(5) 0.5904(5) 0.0484(10) Uani 1 1 d . . . . .
H8 H 0.7248 0.8154 0.5477 0.058 Uiso 1 1 calc R U . . .
C9 C 0.62254(17) 0.6936(4) 0.7986(4) 0.0435(9) Uani 1 1 d . . . . .
C10 C 0.50122(16) 0.6747(4) 0.8055(4) 0.0390(8) Uani 1 1 d . . . . .
C11 C 0.47934(19) 0.7510(5) 0.9347(5) 0.0533(10) Uani 1 1 d . . . . .
H11 H 0.5040 0.8282 0.9718 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4208(2) 0.7126(5) 1.0088(5) 0.0602(11) Uani 1 1 d . . . . .
H12 H 0.4058 0.7653 1.0938 0.072 Uiso 1 1 calc R U . . .
C13 C 0.38510(18) 0.5962(5) 0.9556(5) 0.0556(11) Uani 1 1 d . . . . .
H13 H 0.3462 0.5695 1.0057 0.067 Uiso 1 1 calc R U . . .
C14 C 0.4064(2) 0.5207(5) 0.8310(6) 0.0621(11) Uani 1 1 d . . . . .
H14 H 0.3818 0.4426 0.7954 0.074 Uiso 1 1 calc R U . . .
C15 C 0.46460(19) 0.5585(5) 0.7553(5) 0.0535(10) Uani 1 1 d . . . . .
H15 H 0.4789 0.5051 0.6702 0.064 Uiso 1 1 calc R U . . .
C16 C 0.73899(19) 0.7012(5) 0.8302(5) 0.0606(12) Uani 1 1 d . . . . .
H16A H 0.7546 0.7882 0.8808 0.073 Uiso 1 1 calc R U . . .
H16B H 0.7750 0.6585 0.7717 0.073 Uiso 1 1 calc R U . . .
C17 C 0.7113(2) 0.5972(8) 0.9455(7) 0.093(2) Uani 1 1 d . . . . .
H17A H 0.7318 0.6107 1.0464 0.112 Uiso 1 1 calc R U . . .
H17B H 0.7189 0.4989 0.9119 0.112 Uiso 1 1 calc R U . . .
C18 C 0.63771(19) 0.6281(6) 0.9545(5) 0.0572(11) Uani 1 1 d . . . . .
H18A H 0.6127 0.5401 0.9704 0.069 Uiso 1 1 calc R U . . .
H18B H 0.6279 0.6949 1.0381 0.069 Uiso 1 1 calc R U . . .
N1 N 0.68152(13) 0.7315(3) 0.7289(4) 0.0439(8) Uani 1 1 d . . . . .
B1 B 0.6859(6) 0.0975(14) 0.9110(15) 0.063(2) Uani 0.614(10) 1 d D U P A 1
F1 F 0.6645(4) 0.2168(10) 0.9821(11) 0.089(3) Uani 0.614(10) 1 d D U P A 1
F2 F 0.7171(4) 0.0194(7) 1.0312(9) 0.108(2) Uani 0.614(10) 1 d D U P A 1
F3 F 0.7361(5) 0.1164(15) 0.8133(10) 0.151(4) Uani 0.614(10) 1 d D U P A 1
F4 F 0.6354(3) 0.0144(10) 0.8630(16) 0.129(3) Uani 0.614(10) 1 d D U P A 1
B1' B 0.6856(10) 0.102(2) 0.893(2) 0.073(4) Uani 0.386(10) 1 d D U P A 2
F1' F 0.6737(9) 0.2394(17) 0.905(2) 0.119(5) Uani 0.386(10) 1 d D U P A 2
F2' F 0.6658(9) 0.0186(17) 1.0126(16) 0.147(4) Uani 0.386(10) 1 d D U P A 2
F3' F 0.7482(5) 0.0681(15) 0.885(2) 0.113(4) Uani 0.386(10) 1 d D U P A 2
F4' F 0.6525(6) 0.0597(14) 0.7662(12) 0.092(3) Uani 0.386(10) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C9 1.351(5) . ?
C1 C2 1.427(5) . ?
C1 C10 1.495(5) . ?
C2 C3 1.414(5) . ?
C2 C7 1.429(5) . ?
C3 C4 1.354(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.347(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(5) . ?
C8 N1 1.313(5) . ?
C8 H8 0.9300 . ?
C9 N1 1.380(5) . ?
C9 C18 1.504(6) . ?
C10 C15 1.377(5) . ?
C10 C11 1.390(5) . ?
C11 C12 1.391(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.479(5) . ?
C16 C17 1.494(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.516(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
B1 F3 1.329(13) . ?
B1 F1 1.336(12) . ?
B1 F4 1.345(12) . ?
B1 F2 1.412(13) . ?
B1' F1' 1.298(18) . ?
B1' F3' 1.307(19) . ?
B1' F4' 1.341(19) . ?
B1' F2' 1.35(2) . ?

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
C9 C1 C2 119.0(3) . . ?
C9 C1 C10 119.6(3) . . ?
C2 C1 C10 121.4(3) . . ?
C3 C2 C1 124.3(3) . . ?
C3 C2 C7 117.3(3) . . ?
C1 C2 C7 118.4(3) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 122.2(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 C2 118.6(4) . . ?
C6 C7 C2 120.3(3) . . ?
N1 C8 C7 120.6(3) . . ?
N1 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C1 C9 N1 121.0(3) . . ?
C1 C9 C18 130.7(3) . . ?
N1 C9 C18 108.3(3) . . ?
C15 C10 C11 118.6(4) . . ?
C15 C10 C1 121.5(3) . . ?
C11 C10 C1 119.9(3) . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.4(4) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N1 C16 C17 102.6(3) . . ?
N1 C16 H16A 111.2 . . ?
C17 C16 H16A 111.2 . . ?
N1 C16 H16B 111.2 . . ?
C17 C16 H16B 111.2 . . ?
H16A C16 H16B 109.2 . . ?
C16 C17 C18 106.3(4) . . ?
C16 C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
C16 C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
C9 C18 C17 103.4(3) . . ?
C9 C18 H18A 111.1 . . ?
C17 C18 H18A 111.1 . . ?
C9 C18 H18B 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
C8 N1 C9 122.3(3) . . ?
C8 N1 C16 125.7(3) . . ?
C9 N1 C16 112.0(3) . . ?
F3 B1 F1 115.3(11) . . ?
F3 B1 F4 117.5(12) . . ?
F1 B1 F4 111.7(10) . . ?
F3 B1 F2 100.9(9) . . ?
F1 B1 F2 103.6(10) . . ?
F4 B1 F2 105.6(10) . . ?
F1' B1' F3' 115.1(19) . . ?
F1' B1' F4' 105.2(16) . . ?
F3' B1' F4' 111.4(17) . . ?
F1' B1' F2' 116.7(19) . . ?
F3' B1' F2' 100.9(16) . . ?
F4' B1' F2' 107.5(17) . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

