# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1889593'
loop_
_audit_author_name
_audit_author_address
'Youhei Sohma'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 B F4 N2'
_chemical_formula_weight         298.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   7.87143(14)
_cell_length_b                   10.70505(19)
_cell_length_c                   17.4437(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.4010(10)
_cell_angle_gamma                90.00
_cell_volume                     1423.69(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    21400
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      68.21

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_T_max  0.9018
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25212
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.89
_diffrn_reflns_theta_max         68.21
_reflns_number_total             2606
_reflns_number_gt                2296
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0'

_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2606
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.87415(13) 0.32945(10) 0.41030(6) 0.0362(3) Uani 1 1 d . . .
F2 F 0.42266(14) 0.22597(12) 0.39079(7) 0.0426(3) Uani 1 1 d . . .
F3 F 0.53570(16) 0.24510(12) 0.29174(7) 0.0463(3) Uani 1 1 d . . .
F4 F 0.52218(16) 0.40377(11) 0.36511(8) 0.0501(4) Uani 1 1 d . . .
N1 N 0.79989(19) 0.10958(14) 0.40809(8) 0.0275(3) Uani 1 1 d . . .
N2 N 0.74210(19) 0.24890(13) 0.51328(9) 0.0279(3) Uani 1 1 d . . .
C1 C 0.8581(2) 0.06462(19) 0.34655(11) 0.0333(4) Uani 1 1 d . . .
C2 C 0.8611(2) -0.06592(19) 0.34979(11) 0.0342(4) Uani 1 1 d . . .
H1 H 0.8965 -0.1184 0.3142 0.041 Uiso 1 1 calc R . .
C3 C 0.8029(2) -0.10397(17) 0.41438(10) 0.0297(4) Uani 1 1 d . . .
C4 C 0.7660(2) 0.00663(16) 0.45155(10) 0.0258(4) Uani 1 1 d . . .
C5 C 0.7200(2) 0.02466(17) 0.52238(10) 0.0262(4) Uani 1 1 d . . .
H3 H 0.6947 -0.0447 0.5497 0.031 Uiso 1 1 calc R . .
C6 C 0.7106(2) 0.14223(16) 0.55389(10) 0.0260(4) Uani 1 1 d . . .
C7 C 0.6905(2) 0.17863(18) 0.62923(10) 0.0305(4) Uani 1 1 d . . .
C8 C 0.7114(2) 0.30669(19) 0.63271(11) 0.0344(4) Uani 1 1 d . . .
H2 H 0.7062 0.3570 0.6755 0.041 Uiso 1 1 calc R . .
C9 C 0.7417(2) 0.34840(18) 0.56115(11) 0.0321(4) Uani 1 1 d . . .
C10 C 0.9156(3) 0.1455(2) 0.28790(13) 0.0460(5) Uani 1 1 d . . .
H4A H 0.8309 0.2106 0.2704 0.055 Uiso 1 1 calc R . .
H5B H 0.9254 0.0959 0.2433 0.055 Uiso 1 1 calc R . .
H6C H 1.0274 0.1819 0.3122 0.055 Uiso 1 1 calc R . .
C11 C 0.7833(3) -0.23455(18) 0.44166(13) 0.0370(5) Uani 1 1 d . . .
H7A H 0.8436 -0.2912 0.4149 0.044 Uiso 1 1 calc R . .
H8B H 0.6611 -0.2561 0.4299 0.044 Uiso 1 1 calc R . .
H9C H 0.8326 -0.2400 0.4977 0.044 Uiso 1 1 calc R . .
C12 C 0.6581(3) 0.0924(2) 0.69160(11) 0.0368(5) Uani 1 1 d . . .
H10A H 0.7429 0.0261 0.7003 0.044 Uiso 1 1 calc R . .
H11B H 0.5423 0.0578 0.6745 0.044 Uiso 1 1 calc R . .
H12C H 0.6682 0.1379 0.7399 0.044 Uiso 1 1 calc R . .
C13 C 0.7718(3) 0.47959(19) 0.53897(14) 0.0445(5) Uani 1 1 d . . .
H13A H 0.7585 0.5350 0.5803 0.053 Uiso 1 1 calc R . .
H14B H 0.6880 0.5009 0.4906 0.053 Uiso 1 1 calc R . .
H15C H 0.8882 0.4872 0.5317 0.053 Uiso 1 1 calc R . .
C14 C 0.5588(2) 0.27991(18) 0.36834(11) 0.0312(4) Uani 1 1 d . . .
B1 B 0.7529(3) 0.24492(19) 0.42561(12) 0.0278(4) 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
F1 B1 1.389(2) . ?
F2 C14 1.358(2) . ?
F3 C14 1.355(2) . ?
F4 C14 1.355(2) . ?
N1 C1 1.356(2) . ?
N1 C4 1.400(2) . ?
N1 B1 1.545(2) . ?
N2 C9 1.354(2) . ?
N2 C6 1.398(2) . ?
N2 B1 1.553(2) . ?
C1 C2 1.398(3) . ?
C1 C10 1.494(3) . ?
C2 C3 1.379(3) . ?
C2 H1 0.9300 . ?
C3 C4 1.414(3) . ?
C3 C11 1.497(3) . ?
C4 C5 1.385(2) . ?
C5 C6 1.383(3) . ?
C5 H3 0.9300 . ?
C6 C7 1.417(2) . ?
C7 C8 1.380(3) . ?
C7 C12 1.496(3) . ?
C8 C9 1.401(3) . ?
C8 H2 0.9300 . ?
C9 C13 1.491(3) . ?
C10 H4A 0.9600 . ?
C10 H5B 0.9600 . ?
C10 H6C 0.9600 . ?
C11 H7A 0.9600 . ?
C11 H8B 0.9600 . ?
C11 H9C 0.9600 . ?
C12 H10A 0.9600 . ?
C12 H11B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H14B 0.9600 . ?
C13 H15C 0.9600 . ?
C14 B1 1.647(3) . ?

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
C1 N1 C4 107.26(15) . . ?
C1 N1 B1 129.37(15) . . ?
C4 N1 B1 122.94(14) . . ?
C9 N2 C6 107.58(15) . . ?
C9 N2 B1 129.64(15) . . ?
C6 N2 B1 122.45(14) . . ?
N1 C1 C2 109.17(16) . . ?
N1 C1 C10 123.79(18) . . ?
C2 C1 C10 126.99(18) . . ?
C3 C2 C1 108.81(16) . . ?
C3 C2 H1 125.6 . . ?
C1 C2 H1 125.6 . . ?
C2 C3 C4 105.97(16) . . ?
C2 C3 C11 128.09(17) . . ?
C4 C3 C11 125.94(17) . . ?
C5 C4 N1 120.04(16) . . ?
C5 C4 C3 130.91(16) . . ?
N1 C4 C3 108.79(15) . . ?
C6 C5 C4 122.24(16) . . ?
C6 C5 H3 118.9 . . ?
C4 C5 H3 118.9 . . ?
C5 C6 N2 120.54(15) . . ?
C5 C6 C7 130.43(16) . . ?
N2 C6 C7 108.68(16) . . ?
C8 C7 C6 105.93(16) . . ?
C8 C7 C12 128.38(17) . . ?
C6 C7 C12 125.67(17) . . ?
C7 C8 C9 108.79(16) . . ?
C7 C8 H2 125.6 . . ?
C9 C8 H2 125.6 . . ?
N2 C9 C8 109.02(17) . . ?
N2 C9 C13 123.77(17) . . ?
C8 C9 C13 127.20(18) . . ?
C1 C10 H4A 109.5 . . ?
C1 C10 H5B 109.5 . . ?
H4A C10 H5B 109.5 . . ?
C1 C10 H6C 109.5 . . ?
H4A C10 H6C 109.5 . . ?
H5B C10 H6C 109.5 . . ?
C3 C11 H7A 109.5 . . ?
C3 C11 H8B 109.5 . . ?
H7A C11 H8B 109.5 . . ?
C3 C11 H9C 109.5 . . ?
H7A C11 H9C 109.5 . . ?
H8B C11 H9C 109.5 . . ?
C7 C12 H10A 109.5 . . ?
C7 C12 H11B 109.5 . . ?
H10A C12 H11B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H10A C12 H12C 109.5 . . ?
H11B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H14B 109.5 . . ?
H13A C13 H14B 109.5 . . ?
C9 C13 H15C 109.5 . . ?
H13A C13 H15C 109.5 . . ?
H14B C13 H15C 109.5 . . ?
F3 C14 F4 104.66(14) . . ?
F3 C14 F2 104.21(15) . . ?
F4 C14 F2 104.66(15) . . ?
F3 C14 B1 114.35(15) . . ?
F4 C14 B1 113.78(15) . . ?
F2 C14 B1 114.07(14) . . ?
F1 B1 N1 111.30(15) . . ?
F1 B1 N2 112.34(15) . . ?
N1 B1 N2 107.15(14) . . ?
F1 B1 C14 108.27(15) . . ?
N1 B1 C14 108.96(15) . . ?
N2 B1 C14 108.75(14) . . ?

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
C4 N1 C1 C2 0.28(19) . . . . ?
B1 N1 C1 C2 -172.22(16) . . . . ?
C4 N1 C1 C10 -177.41(18) . . . . ?
B1 N1 C1 C10 10.1(3) . . . . ?
N1 C1 C2 C3 0.3(2) . . . . ?
C10 C1 C2 C3 177.88(19) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C11 179.91(17) . . . . ?
C1 N1 C4 C5 174.00(15) . . . . ?
B1 N1 C4 C5 -12.9(2) . . . . ?
C1 N1 C4 C3 -0.73(18) . . . . ?
B1 N1 C4 C3 172.37(15) . . . . ?
C2 C3 C4 C5 -173.07(18) . . . . ?
C11 C3 C4 C5 6.3(3) . . . . ?
C2 C3 C4 N1 0.89(19) . . . . ?
C11 C3 C4 N1 -179.71(16) . . . . ?
N1 C4 C5 C6 -1.8(3) . . . . ?
C3 C4 C5 C6 171.57(17) . . . . ?
C4 C5 C6 N2 2.1(3) . . . . ?
C4 C5 C6 C7 -170.15(17) . . . . ?
C9 N2 C6 C5 -173.86(15) . . . . ?
B1 N2 C6 C5 12.2(2) . . . . ?
C9 N2 C6 C7 -0.07(19) . . . . ?
B1 N2 C6 C7 -174.03(15) . . . . ?
C5 C6 C7 C8 172.64(18) . . . . ?
N2 C6 C7 C8 -0.33(19) . . . . ?
C5 C6 C7 C12 -5.9(3) . . . . ?
N2 C6 C7 C12 -178.88(16) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C12 C7 C8 C9 179.10(18) . . . . ?
C6 N2 C9 C8 0.4(2) . . . . ?
B1 N2 C9 C8 173.83(16) . . . . ?
C6 N2 C9 C13 179.67(17) . . . . ?
B1 N2 C9 C13 -6.9(3) . . . . ?
C7 C8 C9 N2 -0.7(2) . . . . ?
C7 C8 C9 C13 -179.86(18) . . . . ?
C1 N1 B1 F1 -42.0(2) . . . . ?
C4 N1 B1 F1 146.52(15) . . . . ?
C1 N1 B1 N2 -165.19(16) . . . . ?
C4 N1 B1 N2 23.3(2) . . . . ?
C1 N1 B1 C14 77.3(2) . . . . ?
C4 N1 B1 C14 -94.16(18) . . . . ?
C9 N2 B1 F1 42.0(2) . . . . ?
C6 N2 B1 F1 -145.46(15) . . . . ?
C9 N2 B1 N1 164.56(16) . . . . ?
C6 N2 B1 N1 -22.9(2) . . . . ?
C9 N2 B1 C14 -77.8(2) . . . . ?
C6 N2 B1 C14 94.72(18) . . . . ?
F3 C14 B1 F1 75.98(19) . . . . ?
F4 C14 B1 F1 -44.2(2) . . . . ?
F2 C14 B1 F1 -164.20(15) . . . . ?
F3 C14 B1 N1 -45.2(2) . . . . ?
F4 C14 B1 N1 -165.41(14) . . . . ?
F2 C14 B1 N1 74.60(19) . . . . ?
F3 C14 B1 N2 -161.70(14) . . . . ?
F4 C14 B1 N2 78.10(18) . . . . ?
F2 C14 B1 N2 -41.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        68.21
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.075
