# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_KT-62-A
_database_code_depnum_ccdc_archive 'CCDC 1867227'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H19 B F4 N2'
_chemical_formula_weight         470.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   31.900(4)
_cell_length_b                   9.7621(10)
_cell_length_c                   15.5417(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.394(14)
_cell_angle_gamma                90
_cell_volume                     4618.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1332
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      17.60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17629
_diffrn_reflns_av_unetI/netI     0.1169
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.338
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4093
_reflns_number_gt                1585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0923P] 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_number_reflns         4093
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2352
_refine_ls_R_factor_gt           0.1092
_refine_ls_wR_factor_ref         0.3187
_refine_ls_wR_factor_gt          0.2628
_refine_ls_goodness_of_fit_ref   1.349
_refine_ls_restrained_S_all      1.349
_refine_ls_shift/su_max          0.000
_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
C29 C 0.0534(2) 0.1042(6) -0.0378(4) 0.0708(16) Uani 1 1 d . . . . .
C30 C 0.11663(19) -0.0981(6) -0.0022(4) 0.0664(16) Uani 1 1 d . . . . .
N3 N 0.09245(16) 0.1243(4) 0.0251(3) 0.0655(13) Uani 1 1 d . . . . .
C23 C 0.0736(2) -0.1326(6) -0.0519(4) 0.0707(17) Uani 1 1 d . . . . .
C28 C 0.0415(2) -0.0274(6) -0.0731(4) 0.0701(16) Uani 1 1 d . . . . .
C8 C 0.0975(2) 0.2451(6) 0.0783(5) 0.0687(17) Uani 1 1 d . . . . .
C11 C 0.1717(2) 0.0666(6) 0.0848(4) 0.0692(16) Uani 1 1 d . . . . .
C10 C 0.12653(19) 0.0266(6) 0.0372(4) 0.0665(16) Uani 1 1 d . . . . .
C3 C 0.0677(2) 0.3521(7) 0.0447(5) 0.0790(18) Uani 1 1 d . . . . .
C16 C 0.1917(2) 0.1763(6) 0.0544(5) 0.0798(18) Uani 1 1 d . . . . .
H16 H 0.1762 0.2240 0.0029 0.096 Uiso 1 1 calc R U . . .
N4 N 0.0328(2) 0.3392(6) -0.0336(5) 0.0953(18) Uani 1 1 d . . . . .
C24 C 0.0605(2) -0.2669(7) -0.0854(5) 0.0847(19) Uani 1 1 d . . . . .
H24 H 0.0810 -0.3376 -0.0728 0.102 Uiso 1 1 calc R U . . .
C7 C 0.1267(2) 0.2555(6) 0.1637(5) 0.0784(18) Uani 1 1 d . . . . .
H7 H 0.1457 0.1836 0.1876 0.094 Uiso 1 1 calc R U . . .
C17 C 0.1517(2) -0.2006(6) 0.0001(5) 0.0742(18) Uani 1 1 d . . . . .
C6 C 0.1275(2) 0.3728(7) 0.2137(5) 0.094(2) Uani 1 1 d . . . . .
H6 H 0.1469 0.3784 0.2717 0.113 Uiso 1 1 calc R U . . .
C26 C -0.0121(2) -0.1889(9) -0.1572(5) 0.093(2) Uani 1 1 d . . . . .
H26 H -0.0406 -0.2083 -0.1923 0.111 Uiso 1 1 calc R U . . .
C27 C -0.0012(2) -0.0574(7) -0.1279(4) 0.0822(19) Uani 1 1 d . . . . .
H27 H -0.0221 0.0119 -0.1443 0.099 Uiso 1 1 calc R U . . .
C21 C 0.1578(2) -0.3116(6) 0.0587(5) 0.092(2) Uani 1 1 d . . . . .
H21 H 0.1428 -0.3163 0.1016 0.110 Uiso 1 1 calc R U . . .
C25 C 0.0185(3) -0.2927(7) -0.1355(4) 0.089(2) Uani 1 1 d . . . . .
H25 H 0.0103 -0.3813 -0.1555 0.107 Uiso 1 1 calc R U . . .
C5 C 0.0999(3) 0.4831(7) 0.1790(6) 0.103(2) Uani 1 1 d . . . . .
H5 H 0.1016 0.5631 0.2124 0.124 Uiso 1 1 calc R U . . .
C15 C 0.2341(3) 0.2141(6) 0.1004(6) 0.093(2) Uani 1 1 d . . . . .
H15 H 0.2468 0.2887 0.0804 0.111 Uiso 1 1 calc R U . . .
C4 C 0.0707(3) 0.4719(6) 0.0959(6) 0.097(2) Uani 1 1 d . . . . .
H4 H 0.0522 0.5452 0.0722 0.116 Uiso 1 1 calc R U . . .
C12 C 0.1963(2) -0.0044(6) 0.1595(5) 0.0804(18) Uani 1 1 d . . . . .
H12 H 0.1837 -0.0784 0.1801 0.096 Uiso 1 1 calc R U . . .
C18 C 0.1740(2) -0.1917(6) -0.0626(5) 0.090(2) Uani 1 1 d . . . . .
H18 H 0.1699 -0.1171 -0.1014 0.108 Uiso 1 1 calc R U . . .
C1 C 0.0253(2) 0.2198(8) -0.0671(5) 0.092(2) Uani 1 1 d . . . . .
H1 H -0.0003 0.2067 -0.1143 0.110 Uiso 1 1 calc R U . . .
C14 C 0.2575(2) 0.1439(9) 0.1742(6) 0.107(2) Uani 1 1 d . . . . .
H14 H 0.2860 0.1709 0.2051 0.129 Uiso 1 1 calc R U . . .
C13 C 0.2389(2) 0.0308(8) 0.2042(5) 0.099(2) Uani 1 1 d . . . . .
H13 H 0.2551 -0.0197 0.2538 0.119 Uiso 1 1 calc R U . . .
C22 C 0.1863(3) -0.4145(8) 0.0523(6) 0.121(3) Uani 1 1 d . . . . .
H22 H 0.1910 -0.4886 0.0917 0.145 Uiso 1 1 calc R U . . .
C19 C 0.2028(2) -0.2962(9) -0.0673(6) 0.111(3) Uani 1 1 d . . . . .
H19 H 0.2189 -0.2899 -0.1082 0.133 Uiso 1 1 calc R U . . .
C20 C 0.2078(3) -0.4077(9) -0.0125(8) 0.131(4) Uani 1 1 d . . . . .
H20 H 0.2258 -0.4796 -0.0187 0.157 Uiso 1 1 calc R U . . .
B1 B 0.3907(4) 0.3575(10) 0.2133(18) 0.188(9) Uani 1 1 d . . . . .
F4 F 0.3574(2) 0.2980(7) 0.2190(6) 0.238(3) Uani 1 1 d . . . . .
F3 F 0.4130(3) 0.3216(8) 0.3104(6) 0.259(5) Uani 1 1 d . . . . .
F2 F 0.39561(19) 0.4855(5) 0.2248(5) 0.217(3) Uani 1 1 d . . . . .
F1 F 0.4174(4) 0.2969(7) 0.1909(8) 0.334(7) Uani 1 1 d . . . . .


_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
C29 N3 1.348(7) . ?
C29 C28 1.404(7) . ?
C29 C1 1.428(8) . ?
C30 C10 1.357(7) . ?
C30 C23 1.401(7) . ?
C30 C17 1.494(8) . ?
N3 C10 1.415(6) . ?
N3 C8 1.422(7) . ?
C23 C28 1.416(8) . ?
C23 C24 1.427(8) . ?
C28 C27 1.406(8) . ?
C8 C7 1.378(8) . ?
C8 C3 1.405(8) . ?
C11 C12 1.378(7) . ?
C11 C16 1.397(8) . ?
C11 C10 1.463(8) . ?
C3 N4 1.388(8) . ?
C3 C4 1.401(8) . ?
C16 C15 1.380(9) . ?
N4 C1 1.270(7) . ?
C24 C25 1.356(8) . ?
C7 C6 1.379(8) . ?
C17 C18 1.370(8) . ?
C17 C21 1.391(8) . ?
C6 C5 1.394(8) . ?
C26 C27 1.371(8) . ?
C26 C25 1.376(8) . ?
C21 C22 1.379(9) . ?
C5 C4 1.353(9) . ?
C15 C14 1.353(9) . ?
C12 C13 1.370(8) . ?
C18 C19 1.391(9) . ?
C14 C13 1.399(9) . ?
C22 C20 1.381(11) . ?
C19 C20 1.362(11) . ?
B1 F1 1.173(12) . ?
B1 F4 1.236(11) . ?
B1 F2 1.265(11) . ?
B1 F3 1.50(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
N3 C29 C28 120.0(6) . . ?
N3 C29 C1 118.1(6) . . ?
C28 C29 C1 121.9(6) . . ?
C10 C30 C23 121.4(5) . . ?
C10 C30 C17 121.3(5) . . ?
C23 C30 C17 117.2(5) . . ?
C29 N3 C10 120.3(5) . . ?
C29 N3 C8 117.6(5) . . ?
C10 N3 C8 122.1(5) . . ?
C30 C23 C28 118.4(6) . . ?
C30 C23 C24 123.6(6) . . ?
C28 C23 C24 118.0(6) . . ?
C29 C28 C27 121.8(6) . . ?
C29 C28 C23 118.7(6) . . ?
C27 C28 C23 119.5(6) . . ?
C7 C8 C3 119.3(6) . . ?
C7 C8 N3 123.2(5) . . ?
C3 C8 N3 117.0(6) . . ?
C12 C11 C16 117.9(6) . . ?
C12 C11 C10 121.2(6) . . ?
C16 C11 C10 120.8(6) . . ?
C30 C10 N3 118.6(5) . . ?
C30 C10 C11 121.9(5) . . ?
N3 C10 C11 119.3(5) . . ?
N4 C3 C4 118.3(7) . . ?
N4 C3 C8 122.3(6) . . ?
C4 C3 C8 119.1(7) . . ?
C15 C16 C11 120.4(6) . . ?
C1 N4 C3 116.5(6) . . ?
C25 C24 C23 120.7(6) . . ?
C8 C7 C6 119.8(6) . . ?
C18 C17 C21 121.0(6) . . ?
C18 C17 C30 119.0(6) . . ?
C21 C17 C30 119.6(7) . . ?
C7 C6 C5 121.4(7) . . ?
C27 C26 C25 121.2(7) . . ?
C26 C27 C28 119.9(6) . . ?
C22 C21 C17 119.1(8) . . ?
C24 C25 C26 120.7(6) . . ?
C4 C5 C6 118.8(7) . . ?
C14 C15 C16 120.7(7) . . ?
C5 C4 C3 121.3(7) . . ?
C13 C12 C11 122.0(6) . . ?
C17 C18 C19 118.9(7) . . ?
N4 C1 C29 124.9(7) . . ?
C15 C14 C13 120.1(7) . . ?
C12 C13 C14 118.9(7) . . ?
C21 C22 C20 120.0(8) . . ?
C20 C19 C18 120.6(8) . . ?
C19 C20 C22 120.3(8) . . ?
F1 B1 F4 119.9(12) . . ?
F1 B1 F2 118.0(11) . . ?
F4 B1 F2 121.9(11) . . ?
F1 B1 F3 90.7(13) . . ?
F4 B1 F3 88.8(15) . . ?
F2 B1 F3 95.0(16) . . ?

_refine_diff_density_max         0.869
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.075

