# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_b17006
_database_code_depnum_ccdc_archive 'CCDC 1500180'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-11-03 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            'C17 H12 B F2 N5 O'
_chemical_formula_weight         351.13
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'
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'
B B 0.0013 0.0007 '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                   10.248(6)
_cell_length_b                   14.634(7)
_cell_length_c                   11.146(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.352(18)
_cell_angle_gamma                90
_cell_volume                     1595.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    3704
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.59
_exptl_crystal_description       Prism
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17926
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.750
_diffrn_reflns_theta_max         31.721
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2694
_reflns_number_gt                1822
_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       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_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)+(0.0434P)²+0.7408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2694
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
B1 B 0.5000 0.17993(13) 0.2500 0.0202(4) Uani 1 2 d S T P . .
F1 F 0.60845(7) 0.12746(5) 0.24266(6) 0.02546(19) Uani 1 1 d . . . . .
N1 N 0.54432(10) 0.24448(7) 0.36842(8) 0.0201(2) Uani 1 1 d . . . . .
N2 N 0.54202(10) 0.33341(7) 0.36363(9) 0.0233(2) Uani 1 1 d . . . . .
N3 N 0.5000 0.54886(11) 0.2500 0.0379(4) Uani 1 2 d S T P . .
C1 C 0.5000 0.37195(12) 0.2500 0.0234(3) Uani 1 2 d S T P . .
C2 C 0.5000 0.47059(13) 0.2500 0.0297(4) Uani 1 2 d S T P . .
C3 C 0.58701(12) 0.20757(8) 0.49281(10) 0.0214(2) Uani 1 1 d . . . . .
C4 C 0.60638(12) 0.11392(9) 0.51073(10) 0.0243(3) Uani 1 1 d . . . . .
H4 H 0.5946(15) 0.0706(10) 0.4406(14) 0.030(4) Uiso 1 1 d . . . . .
C5 C 0.64763(13) 0.07866(10) 0.63168(11) 0.0289(3) Uani 1 1 d . . . . .
H5 H 0.6630(16) 0.0153(11) 0.6480(13) 0.032(4) Uiso 1 1 d . . . . .
C6 C 0.67072(12) 0.13730(11) 0.73508(11) 0.0308(3) Uani 1 1 d . . . . .
C7 C 0.65062(14) 0.23034(11) 0.71642(12) 0.0342(3) Uani 1 1 d . . . . .
H7 H 0.6650(16) 0.2716(11) 0.7863(14) 0.039(4) Uiso 1 1 d . . . . .
C8 C 0.60891(13) 0.26606(10) 0.59627(11) 0.0289(3) Uani 1 1 d . . . . .
H8 H 0.5947(16) 0.3321(12) 0.5827(14) 0.037(4) Uiso 1 1 d . . . . .
O1 O 0.7155(4) 0.08232(19) 0.8481(3) 0.0288(7) Uani 0.5 1 d . . P A 1
C11 C 0.7460(4) 0.1355(3) 0.9594(3) 0.0313(8) Uani 0.5 1 d . . P A 1
H11A H 0.778(5) 0.092(3) 1.046(4) 0.039(12) Uiso 0.5 1 d . . P B 1
H11B H 0.814(4) 0.185(2) 0.957(3) 0.043(9) Uiso 0.5 1 d . . P C 1
H11C H 0.663(4) 0.169(2) 0.969(3) 0.044(9) Uiso 0.5 1 d . . P D 1
C9 C 0.7198(6) 0.1170(3) 0.8630(5) 0.0286(9) Uani 0.5 1 d . . P A 2
C10 C 0.7695(5) 0.0955(3) 0.9700(4) 0.0383(10) Uani 0.5 1 d . . P A 2
H10 H 0.825(6) 0.081(4) 1.039(6) 0.08(2) Uiso 0.5 1 d . . P E 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
B1 F1 1.3732(14) 2_655 ?
B1 F1 1.3733(14) . ?
B1 N1 1.5759(15) . ?
B1 N1 1.5759(15) 2_655 ?
N1 N2 1.3023(15) . ?
N1 C3 1.4296(15) . ?
N2 C1 1.3351(13) . ?
N3 C2 1.146(2) . ?
C1 N2 1.3351(13) 2_655 ?
C1 C2 1.443(3) . ?
C3 C4 1.3907(19) . ?
C3 C8 1.3994(17) . ?
C4 C5 1.3866(17) . ?
C4 H4 0.985(15) . ?
C5 C6 1.399(2) . ?
C5 H5 0.949(16) . ?
C6 C7 1.383(2) . ?
C6 C9 1.395(6) . ?
C6 O1 1.449(4) . ?
C7 C8 1.3814(19) . ?
C7 H7 0.961(16) . ?
C8 H8 0.982(17) . ?
O1 C11 1.418(5) . ?
C11 H11A 1.12(5) . ?
C11 H11B 1.01(4) . ?
C11 H11C 1.01(4) . ?
C9 C10 1.191(7) . ?
C10 H10 0.83(6) . ?

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
F1 B1 F1 112.01(15) 2_655 . ?
F1 B1 N1 108.75(5) 2_655 . ?
F1 B1 N1 110.42(5) . . ?
F1 B1 N1 110.42(5) 2_655 2_655 ?
F1 B1 N1 108.75(5) . 2_655 ?
N1 B1 N1 106.34(13) . 2_655 ?
N2 N1 C3 114.45(9) . . ?
N2 N1 B1 124.57(10) . . ?
C3 N1 B1 120.95(10) . . ?
N1 N2 C1 117.24(11) . . ?
N2 C1 N2 130.03(16) 2_655 . ?
N2 C1 C2 114.99(8) 2_655 . ?
N2 C1 C2 114.99(8) . . ?
N3 C2 C1 180.0 . . ?
C4 C3 C8 120.23(11) . . ?
C4 C3 N1 120.06(10) . . ?
C8 C3 N1 119.71(12) . . ?
C5 C4 C3 119.70(12) . . ?
C5 C4 H4 117.5(9) . . ?
C3 C4 H4 122.7(9) . . ?
C4 C5 C6 120.01(14) . . ?
C4 C5 H5 122.4(9) . . ?
C6 C5 H5 117.6(9) . . ?
C7 C6 C9 110.8(2) . . ?
C7 C6 C5 119.92(12) . . ?
C9 C6 C5 129.2(2) . . ?
C7 C6 O1 132.16(15) . . ?
C5 C6 O1 107.92(16) . . ?
C8 C7 C6 120.49(12) . . ?
C8 C7 H7 118.4(9) . . ?
C6 C7 H7 121.1(9) . . ?
C7 C8 C3 119.65(14) . . ?
C7 C8 H8 120.7(9) . . ?
C3 C8 H8 119.7(9) . . ?
C11 O1 C6 112.7(3) . . ?
O1 C11 H11A 112(2) . . ?
O1 C11 H11B 110.4(18) . . ?
H11A C11 H11B 113(3) . . ?
O1 C11 H11C 112.3(19) . . ?
H11A C11 H11C 103(3) . . ?
H11B C11 H11C 106(3) . . ?
C10 C9 C6 174.8(6) . . ?
C9 C10 H10 163(4) . . ?

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
F1 B1 N1 N2 -118.64(12) 2_655 . . . ?
F1 B1 N1 N2 118.09(12) . . . . ?
N1 B1 N1 N2 0.28(7) 2_655 . . . ?
F1 B1 N1 C3 59.24(12) 2_655 . . . ?
F1 B1 N1 C3 -64.03(12) . . . . ?
N1 B1 N1 C3 178.15(11) 2_655 . . . ?
C3 N1 N2 C1 -178.52(8) . . . . ?
B1 N1 N2 C1 -0.53(14) . . . . ?
N1 N2 C1 N2 0.27(7) . . . 2_655 ?
N1 N2 C1 C2 -179.73(7) . . . . ?
N2 N1 C3 C4 -173.86(11) . . . . ?
B1 N1 C3 C4 8.06(15) . . . . ?
N2 N1 C3 C8 6.26(16) . . . . ?
B1 N1 C3 C8 -171.82(9) . . . . ?
C8 C3 C4 C5 -0.04(18) . . . . ?
N1 C3 C4 C5 -179.92(11) . . . . ?
C3 C4 C5 C6 -0.55(18) . . . . ?
C4 C5 C6 C7 0.84(19) . . . . ?
C4 C5 C6 C9 -175.8(3) . . . . ?
C4 C5 C6 O1 -178.66(19) . . . . ?
C9 C6 C7 C8 176.7(3) . . . . ?
C5 C6 C7 C8 -0.54(19) . . . . ?
O1 C6 C7 C8 178.8(2) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C4 C3 C8 C7 0.34(19) . . . . ?
N1 C3 C8 C7 -179.78(11) . . . . ?
C7 C6 O1 C11 -1.3(5) . . . . ?
C5 C6 O1 C11 178.2(3) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046


_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
