# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_tc
_database_code_depnum_ccdc_archive 'CCDC 1409236'
_audit_update_record             
;
2016-03-27 deposited with the CCDC.
2016-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 B F2 N3 O'
_chemical_formula_sum            'C17 H12 B F2 N3 O'
_chemical_formula_weight         323.01

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

loop_
_symmetry_equiv_pos_as_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                   20.469(4)
_cell_length_b                   10.079(2)
_cell_length_c                   6.7220(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1386.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2966
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      29.1

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            10342
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2418
_reflns_number_gt                2260
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CAMERON (Watkin, Prout & Pearce,  1996)'
_computing_publication_material  
'CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)'

_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)+(0.1000P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.0(12)
_refine_ls_number_reflns         2418
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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 0.37272(9) 0.28581(19) 0.4146(3) 0.0202(5) Uani 1 1 d . . .
F2 F 0.36941(9) 0.27617(18) 0.0778(3) 0.0203(5) Uani 1 1 d . . .
O1 O 0.07600(10) 0.2955(2) 0.3193(4) 0.0193(5) Uani 1 1 d . . .
N2 N 0.30069(11) 0.4382(2) 0.2443(4) 0.0141(5) Uani 1 1 d . . .
N3 N 0.44539(11) 0.5018(2) 0.1464(4) 0.0158(6) Uani 1 1 d . . .
H3A H 0.4369 0.4257 0.0945 0.019 Uiso 1 1 calc R . .
N1 N 0.27564(11) 0.1972(2) 0.2596(5) 0.0144(5) Uani 1 1 d . . .
C14 C 0.11836(13) 0.3889(3) 0.2419(6) 0.0158(6) Uani 1 1 d . . .
C9 C 0.33168(14) 0.5575(2) 0.2510(5) 0.0143(6) Uani 1 1 d . . .
C6 C 0.23294(12) 0.4620(3) 0.2551(6) 0.0140(6) Uani 1 1 d . . .
C10 C 0.40052(13) 0.5822(2) 0.2392(5) 0.0148(6) Uani 1 1 d . . .
C8 C 0.28405(13) 0.6595(3) 0.2715(5) 0.0162(6) Uani 1 1 d . . .
H8A H 0.2925 0.7499 0.2821 0.019 Uiso 1 1 calc R . .
C5 C 0.18777(14) 0.3590(2) 0.2551(5) 0.0148(6) Uani 1 1 d . . .
C15 C 0.08307(15) 0.4865(3) 0.1528(5) 0.0164(7) Uani 1 1 d . . .
H15A H 0.0997 0.5613 0.0897 0.020 Uiso 1 1 calc R . .
C3 C 0.17542(14) 0.1033(3) 0.2559(5) 0.0182(6) Uani 1 1 d . . .
H3B H 0.1303 0.0921 0.2545 0.022 Uiso 1 1 calc R . .
C16 C 0.01618(14) 0.4532(3) 0.1738(5) 0.0192(7) Uani 1 1 d . . .
H16A H -0.0194 0.5012 0.1267 0.023 Uiso 1 1 calc R . .
C1 C 0.28298(14) 0.0632(2) 0.2558(5) 0.0162(6) Uani 1 1 d . . .
H1A H 0.3227 0.0185 0.2542 0.019 Uiso 1 1 calc R . .
C17 C 0.01433(13) 0.3382(3) 0.2755(5) 0.0197(7) Uani 1 1 d . . .
H17A H -0.0238 0.2939 0.3112 0.024 Uiso 1 1 calc R . .
C2 C 0.22170(14) 0.0035(3) 0.2545(6) 0.0183(6) Uani 1 1 d . . .
H2A H 0.2134 -0.0872 0.2529 0.022 Uiso 1 1 calc R . .
C4 C 0.20912(14) 0.2249(3) 0.2600(5) 0.0144(6) Uani 1 1 d . . .
C11 C 0.43398(15) 0.6943(3) 0.3041(5) 0.0173(7) Uani 1 1 d . . .
H11A H 0.4160 0.7660 0.3717 0.021 Uiso 1 1 calc R . .
C7 C 0.22386(14) 0.6012(3) 0.2729(5) 0.0174(7) Uani 1 1 d . . .
H7A H 0.1840 0.6449 0.2835 0.021 Uiso 1 1 calc R . .
C13 C 0.50545(15) 0.5607(3) 0.1489(5) 0.0200(7) Uani 1 1 d . . .
H13A H 0.5435 0.5265 0.0929 0.024 Uiso 1 1 calc R . .
C12 C 0.49992(14) 0.6798(3) 0.2492(6) 0.0188(7) Uani 1 1 d . . .
H12A H 0.5335 0.7394 0.2756 0.023 Uiso 1 1 calc R . .
B1 B 0.33128(15) 0.2976(3) 0.2496(7) 0.0151(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
F1 B1 1.402(4) . ?
F2 B1 1.410(4) . ?
O1 C17 1.366(3) . ?
O1 C14 1.382(3) . ?
N2 C9 1.360(3) . ?
N2 C6 1.409(3) . ?
N2 B1 1.550(4) . ?
N3 C13 1.365(4) . ?
N3 C10 1.375(4) . ?
N3 H3A 0.8600 . ?
N1 C1 1.359(3) . ?
N1 C4 1.390(3) . ?
N1 B1 1.525(4) . ?
C14 C15 1.360(4) . ?
C14 C5 1.455(4) . ?
C9 C8 1.424(4) . ?
C9 C10 1.433(4) . ?
C6 C5 1.390(4) . ?
C6 C7 1.420(4) . ?
C10 C11 1.391(4) . ?
C8 C7 1.365(4) . ?
C8 H8A 0.9300 . ?
C5 C4 1.421(4) . ?
C15 C16 1.417(4) . ?
C15 H15A 0.9300 . ?
C3 C2 1.382(4) . ?
C3 C4 1.407(4) . ?
C3 H3B 0.9300 . ?
C16 C17 1.346(5) . ?
C16 H16A 0.9300 . ?
C1 C2 1.391(4) . ?
C1 H1A 0.9300 . ?
C17 H17A 0.9300 . ?
C2 H2A 0.9300 . ?
C11 C12 1.407(4) . ?
C11 H11A 0.9300 . ?
C7 H7A 0.9300 . ?
C13 C12 1.382(5) . ?
C13 H13A 0.9300 . ?
C12 H12A 0.9300 . ?

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
C17 O1 C14 106.5(2) . . ?
C9 N2 C6 107.9(2) . . ?
C9 N2 B1 128.3(2) . . ?
C6 N2 B1 123.5(2) . . ?
C13 N3 C10 109.8(2) . . ?
C13 N3 H3A 125.1 . . ?
C10 N3 H3A 125.1 . . ?
C1 N1 C4 107.9(2) . . ?
C1 N1 B1 125.2(2) . . ?
C4 N1 B1 126.8(2) . . ?
C15 C14 O1 109.0(2) . . ?
C15 C14 C5 134.1(3) . . ?
O1 C14 C5 116.7(2) . . ?
N2 C9 C8 108.8(2) . . ?
N2 C9 C10 127.6(2) . . ?
C8 C9 C10 123.6(2) . . ?
C5 C6 N2 121.8(2) . . ?
C5 C6 C7 130.6(2) . . ?
N2 C6 C7 107.5(2) . . ?
N3 C10 C11 107.0(2) . . ?
N3 C10 C9 125.4(3) . . ?
C11 C10 C9 127.5(3) . . ?
C7 C8 C9 107.9(2) . . ?
C7 C8 H8A 126.0 . . ?
C9 C8 H8A 126.0 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 C14 119.7(2) . . ?
C4 C5 C14 119.9(2) . . ?
C14 C15 C16 107.3(3) . . ?
C14 C15 H15A 126.3 . . ?
C16 C15 H15A 126.3 . . ?
C2 C3 C4 107.4(2) . . ?
C2 C3 H3B 126.3 . . ?
C4 C3 H3B 126.3 . . ?
C17 C16 C15 106.4(3) . . ?
C17 C16 H16A 126.8 . . ?
C15 C16 H16A 126.8 . . ?
N1 C1 C2 109.3(2) . . ?
N1 C1 H1A 125.3 . . ?
C2 C1 H1A 125.3 . . ?
C16 C17 O1 110.8(3) . . ?
C16 C17 H17A 124.6 . . ?
O1 C17 H17A 124.6 . . ?
C3 C2 C1 107.6(2) . . ?
C3 C2 H2A 126.2 . . ?
C1 C2 H2A 126.2 . . ?
N1 C4 C3 107.8(2) . . ?
N1 C4 C5 119.5(2) . . ?
C3 C4 C5 132.7(3) . . ?
C10 C11 C12 107.8(3) . . ?
C10 C11 H11A 126.1 . . ?
C12 C11 H11A 126.1 . . ?
C8 C7 C6 107.8(2) . . ?
C8 C7 H7A 126.1 . . ?
C6 C7 H7A 126.1 . . ?
N3 C13 C12 108.1(3) . . ?
N3 C13 H13A 126.0 . . ?
C12 C13 H13A 126.0 . . ?
C13 C12 C11 107.3(3) . . ?
C13 C12 H12A 126.4 . . ?
C11 C12 H12A 126.4 . . ?
F1 B1 F2 107.5(2) . . ?
F1 B1 N1 111.1(3) . . ?
F2 B1 N1 110.4(3) . . ?
F1 B1 N2 109.9(3) . . ?
F2 B1 N2 110.2(3) . . ?
N1 B1 N2 107.8(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 O1 C14 C15 0.0(3) . . . . ?
C17 O1 C14 C5 -174.8(3) . . . . ?
C6 N2 C9 C8 1.5(4) . . . . ?
B1 N2 C9 C8 -171.6(3) . . . . ?
C6 N2 C9 C10 -178.3(3) . . . . ?
B1 N2 C9 C10 8.6(6) . . . . ?
C9 N2 C6 C5 -178.9(3) . . . . ?
B1 N2 C6 C5 -5.4(5) . . . . ?
C9 N2 C6 C7 -1.2(4) . . . . ?
B1 N2 C6 C7 172.3(3) . . . . ?
C13 N3 C10 C11 -0.8(4) . . . . ?
C13 N3 C10 C9 174.8(3) . . . . ?
N2 C9 C10 N3 26.4(6) . . . . ?
C8 C9 C10 N3 -153.4(3) . . . . ?
N2 C9 C10 C11 -158.9(3) . . . . ?
C8 C9 C10 C11 21.4(6) . . . . ?
N2 C9 C8 C7 -1.3(4) . . . . ?
C10 C9 C8 C7 178.5(3) . . . . ?
N2 C6 C5 C4 5.1(5) . . . . ?
C7 C6 C5 C4 -172.1(4) . . . . ?
N2 C6 C5 C14 -172.5(3) . . . . ?
C7 C6 C5 C14 10.4(6) . . . . ?
C15 C14 C5 C6 31.7(6) . . . . ?
O1 C14 C5 C6 -155.1(3) . . . . ?
C15 C14 C5 C4 -145.8(4) . . . . ?
O1 C14 C5 C4 27.4(5) . . . . ?
O1 C14 C15 C16 -0.3(4) . . . . ?
C5 C14 C15 C16 173.3(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C4 N1 C1 C2 -0.2(4) . . . . ?
B1 N1 C1 C2 -176.1(3) . . . . ?
C15 C16 C17 O1 -0.5(4) . . . . ?
C14 O1 C17 C16 0.3(3) . . . . ?
C4 C3 C2 C1 -0.5(4) . . . . ?
N1 C1 C2 C3 0.5(4) . . . . ?
C1 N1 C4 C3 -0.1(4) . . . . ?
B1 N1 C4 C3 175.7(4) . . . . ?
C1 N1 C4 C5 -177.3(3) . . . . ?
B1 N1 C4 C5 -1.5(5) . . . . ?
C2 C3 C4 N1 0.4(4) . . . . ?
C2 C3 C4 C5 177.1(4) . . . . ?
C6 C5 C4 N1 -1.7(5) . . . . ?
C14 C5 C4 N1 175.9(3) . . . . ?
C6 C5 C4 C3 -178.0(4) . . . . ?
C14 C5 C4 C3 -0.5(6) . . . . ?
N3 C10 C11 C12 -0.2(4) . . . . ?
C9 C10 C11 C12 -175.7(3) . . . . ?
C9 C8 C7 C6 0.5(4) . . . . ?
C5 C6 C7 C8 177.8(4) . . . . ?
N2 C6 C7 C8 0.4(4) . . . . ?
C10 N3 C13 C12 1.5(4) . . . . ?
N3 C13 C12 C11 -1.5(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C1 N1 B1 F1 -63.2(5) . . . . ?
C4 N1 B1 F1 121.7(3) . . . . ?
C1 N1 B1 F2 55.9(5) . . . . ?
C4 N1 B1 F2 -119.2(3) . . . . ?
C1 N1 B1 N2 176.3(3) . . . . ?
C4 N1 B1 N2 1.2(5) . . . . ?
C9 N2 B1 F1 53.0(5) . . . . ?
C6 N2 B1 F1 -119.1(3) . . . . ?
C9 N2 B1 F2 -65.2(4) . . . . ?
C6 N2 B1 F2 122.7(3) . . . . ?
C9 N2 B1 N1 174.3(3) . . . . ?
C6 N2 B1 N1 2.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.052
