# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_140107a_0m
_database_code_depnum_ccdc_archive 'CCDC 995007'
_audit_update_record             
;
2014-04-02 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 B F2 N2'
_chemical_formula_weight         206.00

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7265(7)
_cell_length_b                   7.7446(7)
_cell_length_c                   16.6941(15)
_cell_angle_alpha                102.9460(10)
_cell_angle_beta                 93.5520(10)
_cell_angle_gamma                92.3290(10)
_cell_volume                     970.16(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3207
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8480
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         27.64
_reflns_number_total             4380
_reflns_number_gt                2953
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0696P)²+0.0763P] 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         4380
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.001

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
B1 B 0.2782(3) 0.3818(3) 0.09548(12) 0.0504(5) Uani 1 1 d . . .
B2 B 0.1369(3) 0.7189(3) 0.40881(13) 0.0498(5) Uani 1 1 d . . .
C1 C 0.4829(3) 0.4802(3) 0.22733(11) 0.0632(5) Uani 1 1 d . . .
H1 H 0.4018 0.5402 0.2604 0.076 Uiso 1 1 calc R . .
C2 C 0.6529(3) 0.4573(3) 0.25402(12) 0.0697(6) Uani 1 1 d . . .
H2 H 0.7044 0.4988 0.3071 0.084 Uiso 1 1 calc R . .
C3 C 0.7305(3) 0.3625(3) 0.18786(12) 0.0609(5) Uani 1 1 d . . .
H3 H 0.8442 0.3276 0.1875 0.073 Uiso 1 1 calc R . .
C4 C 0.6052(2) 0.3279(2) 0.12040(10) 0.0475(4) Uani 1 1 d . . .
C5 C 0.6164(2) 0.2419(2) 0.03819(10) 0.0456(4) Uani 1 1 d . . .
C6 C 0.4752(2) 0.2358(2) -0.01878(10) 0.0457(4) Uani 1 1 d . . .
C7 C 0.4569(2) 0.1708(3) -0.10440(11) 0.0579(5) Uani 1 1 d . . .
H7 H 0.5398 0.1127 -0.1369 0.069 Uiso 1 1 calc R . .
C8 C 0.2952(3) 0.2083(3) -0.13144(11) 0.0631(5) Uani 1 1 d . . .
H8 H 0.2478 0.1803 -0.1856 0.076 Uiso 1 1 calc R . .
C9 C 0.2150(2) 0.2958(3) -0.06300(11) 0.0566(5) Uani 1 1 d . . .
H9 H 0.1037 0.3369 -0.0642 0.068 Uiso 1 1 calc R . .
C10 C 0.7805(2) 0.1599(3) 0.01089(13) 0.0622(5) Uani 1 1 d . . .
H10A H 0.8688 0.2516 0.0123 0.093 Uiso 1 1 calc R . .
H10B H 0.7606 0.0891 -0.0443 0.093 Uiso 1 1 calc R . .
H10C H 0.8178 0.0862 0.0471 0.093 Uiso 1 1 calc R . .
C11 C 0.1721(3) 0.7648(3) 0.56695(11) 0.0582(5) Uani 1 1 d . . .
H11 H 0.1246 0.6540 0.5695 0.070 Uiso 1 1 calc R . .
C12 C 0.2436(3) 0.8926(3) 0.63410(11) 0.0674(6) Uani 1 1 d . . .
H12 H 0.2525 0.8828 0.6887 0.081 Uiso 1 1 calc R . .
C13 C 0.2987(3) 1.0357(3) 0.60516(11) 0.0612(5) Uani 1 1 d . . .
H13 H 0.3522 1.1410 0.6365 0.073 Uiso 1 1 calc R . .
C14 C 0.2597(2) 0.9948(2) 0.51942(10) 0.0465(4) Uani 1 1 d . . .
C15 C 0.2808(2) 1.0955(2) 0.46068(11) 0.0478(4) Uani 1 1 d . . .
C16 C 0.2212(2) 1.0248(2) 0.37882(10) 0.0492(4) Uani 1 1 d . . .
C17 C 0.2170(3) 1.1000(3) 0.30922(12) 0.0630(5) Uani 1 1 d . . .
H17 H 0.2577 1.2140 0.3080 0.076 Uiso 1 1 calc R . .
C18 C 0.1423(3) 0.9745(3) 0.24399(13) 0.0711(6) Uani 1 1 d . . .
H18 H 0.1225 0.9872 0.1902 0.085 Uiso 1 1 calc R . .
C19 C 0.1013(3) 0.8240(3) 0.27314(11) 0.0631(5) Uani 1 1 d . . .
H19 H 0.0495 0.7184 0.2412 0.076 Uiso 1 1 calc R . .
C20 C 0.3634(3) 1.2792(2) 0.48561(14) 0.0653(5) Uani 1 1 d . . .
H20A H 0.2747 1.3634 0.4940 0.098 Uiso 1 1 calc R . .
H20B H 0.4335 1.3008 0.4430 0.098 Uiso 1 1 calc R . .
H20C H 0.4350 1.2913 0.5359 0.098 Uiso 1 1 calc R . .
F1 F 0.16998(14) 0.25733(16) 0.11902(7) 0.0709(3) Uani 1 1 d . . .
F2 F 0.19718(15) 0.53956(15) 0.10475(7) 0.0731(3) Uani 1 1 d . . .
F3 F 0.25851(17) 0.59288(15) 0.38678(7) 0.0729(4) Uani 1 1 d . . .
F4 F -0.02643(16) 0.63489(16) 0.40078(7) 0.0763(4) Uani 1 1 d . . .
N1 N 0.45296(18) 0.40361(19) 0.14746(8) 0.0489(3) Uani 1 1 d . . .
N2 N 0.32136(17) 0.31260(18) 0.00519(8) 0.0457(3) Uani 1 1 d . . .
N3 N 0.18146(17) 0.82497(18) 0.49758(8) 0.0461(3) Uani 1 1 d . . .
N4 N 0.14716(18) 0.85335(19) 0.35388(8) 0.0483(3) 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
B1 F2 1.378(2) . ?
B1 F1 1.388(2) . ?
B1 N1 1.541(2) . ?
B1 N2 1.544(2) . ?
B2 F4 1.381(2) . ?
B2 F3 1.388(2) . ?
B2 N3 1.535(2) . ?
B2 N4 1.536(2) . ?
C1 N1 1.334(2) . ?
C1 C2 1.392(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.391(2) . ?
C4 C5 1.394(2) . ?
C5 C6 1.394(2) . ?
C5 C10 1.493(2) . ?
C6 N2 1.392(2) . ?
C6 C7 1.401(2) . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.340(2) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N3 1.346(2) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.406(2) . ?
C13 H13 0.9300 . ?
C14 N3 1.386(2) . ?
C14 C15 1.396(2) . ?
C15 C16 1.395(2) . ?
C15 C20 1.494(3) . ?
C16 N4 1.387(2) . ?
C16 C17 1.411(2) . ?
C17 C18 1.366(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(3) . ?
C18 H18 0.9300 . ?
C19 N4 1.338(2) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
F2 B1 F1 109.13(15) . . ?
F2 B1 N1 111.84(16) . . ?
F1 B1 N1 109.32(15) . . ?
F2 B1 N2 110.85(15) . . ?
F1 B1 N2 109.75(15) . . ?
N1 B1 N2 105.90(14) . . ?
F4 B2 F3 109.18(16) . . ?
F4 B2 N3 110.90(15) . . ?
F3 B2 N3 109.97(14) . . ?
F4 B2 N4 111.34(15) . . ?
F3 B2 N4 109.19(15) . . ?
N3 B2 N4 106.22(14) . . ?
N1 C1 C2 110.22(18) . . ?
N1 C1 H1 124.9 . . ?
C2 C1 H1 124.9 . . ?
C3 C2 C1 107.46(17) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
C2 C3 C4 106.95(18) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
N1 C4 C5 121.05(14) . . ?
N1 C4 C3 107.92(16) . . ?
C5 C4 C3 130.98(17) . . ?
C6 C5 C4 119.91(15) . . ?
C6 C5 C10 120.05(16) . . ?
C4 C5 C10 120.03(15) . . ?
N2 C6 C5 121.02(15) . . ?
N2 C6 C7 107.61(15) . . ?
C5 C6 C7 131.25(16) . . ?
C8 C7 C6 107.63(17) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 C9 107.25(16) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 110.14(17) . . ?
N2 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C12 109.92(17) . . ?
N3 C11 H11 125.0 . . ?
C12 C11 H11 125.0 . . ?
C13 C12 C11 107.31(16) . . ?
C13 C12 H12 126.3 . . ?
C11 C12 H12 126.3 . . ?
C12 C13 C14 107.59(17) . . ?
C12 C13 H13 126.2 . . ?
C14 C13 H13 126.2 . . ?
N3 C14 C15 121.02(15) . . ?
N3 C14 C13 107.60(15) . . ?
C15 C14 C13 131.32(17) . . ?
C16 C15 C14 119.57(15) . . ?
C16 C15 C20 120.19(16) . . ?
C14 C15 C20 120.24(17) . . ?
N4 C16 C15 121.24(15) . . ?
N4 C16 C17 107.63(16) . . ?
C15 C16 C17 131.12(18) . . ?
C18 C17 C16 107.38(18) . . ?
C18 C17 H17 126.3 . . ?
C16 C17 H17 126.3 . . ?
C17 C18 C19 107.24(18) . . ?
C17 C18 H18 126.4 . . ?
C19 C18 H18 126.4 . . ?
N4 C19 C18 110.11(19) . . ?
N4 C19 H19 124.9 . . ?
C18 C19 H19 124.9 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C4 107.44(15) . . ?
C1 N1 B1 127.30(16) . . ?
C4 N1 B1 124.91(14) . . ?
C9 N2 C6 107.37(14) . . ?
C9 N2 B1 127.56(15) . . ?
C6 N2 B1 124.66(14) . . ?
C11 N3 C14 107.58(15) . . ?
C11 N3 B2 126.91(15) . . ?
C14 N3 B2 125.07(14) . . ?
C19 N4 C16 107.64(15) . . ?
C19 N4 B2 127.12(16) . . ?
C16 N4 B2 125.02(14) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_101125b_0m
_database_code_depnum_ccdc_archive 'CCDC 995008'
_audit_update_record             
;
2014-04-02 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 B F2 N2'
_chemical_formula_weight         304.18

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9260(9)
_cell_length_b                   12.1904(10)
_cell_length_c                   13.1824(11)
_cell_angle_alpha                103.9960(10)
_cell_angle_beta                 99.1160(10)
_cell_angle_gamma                90.0380(10)
_cell_volume                     1680.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5589
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9873
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14676
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.54
_reflns_number_total             7576
_reflns_number_gt                5045
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0495P)²+0.4096P] 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     SHELXL
_refine_ls_extinction_coef       0.0056(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7576
_refine_ls_number_parameters     410
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      1.007
_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
B1 B 0.48404(17) 0.97025(16) 0.27069(14) 0.0450(4) Uani 1 1 d . . .
C1 C 0.18397(18) 0.96484(16) 0.19236(19) 0.0725(6) Uani 1 1 d . . .
H1A H 0.1695 1.0154 0.2571 0.109 Uiso 1 1 calc R . .
H1B H 0.1140 0.9633 0.1378 0.109 Uiso 1 1 calc R . .
H1C H 0.2570 0.9905 0.1715 0.109 Uiso 1 1 calc R . .
F1 F 0.44044(9) 1.07769(8) 0.30507(8) 0.0562(3) Uani 1 1 d . . .
N1 N 0.41987(12) 0.88798(11) 0.32342(10) 0.0467(3) Uani 1 1 d . . .
B2 B 0.93794(18) 0.46672(17) 0.27072(15) 0.0510(4) Uani 1 1 d . . .
C2 C 0.23420(19) 0.76477(18) 0.10923(16) 0.0724(5) Uani 1 1 d . . .
H2A H 0.3103 0.7908 0.0934 0.109 Uiso 1 1 calc R . .
H2B H 0.1686 0.7627 0.0509 0.109 Uiso 1 1 calc R . .
H2C H 0.2437 0.6902 0.1208 0.109 Uiso 1 1 calc R . .
F2 F 0.45807(9) 0.93311(9) 0.16281(7) 0.0595(3) Uani 1 1 d . . .
N2 N 0.62782(12) 0.97584(11) 0.30970(10) 0.0462(3) Uani 1 1 d . . .
C3 C 0.20222(16) 0.84570(15) 0.20946(16) 0.0590(4) Uani 1 1 d . . .
F3 F 0.91686(9) 0.43430(9) 0.16274(7) 0.0639(3) Uani 1 1 d . . .
N3 N 0.81215(14) 0.47007(12) 0.31478(10) 0.0540(4) Uani 1 1 d . . .
C4 C 0.0770(2) 0.8039(2) 0.2291(2) 0.0909(7) Uani 1 1 d . . .
H4A H 0.0822 0.7266 0.2337 0.136 Uiso 1 1 calc R . .
H4B H 0.0131 0.8092 0.1717 0.136 Uiso 1 1 calc R . .
H4C H 0.0576 0.8498 0.2943 0.136 Uiso 1 1 calc R . .
F4 F 0.99509(9) 0.57388(8) 0.30727(8) 0.0625(3) Uani 1 1 d . . .
N4 N 1.02505(14) 0.38188(12) 0.31655(11) 0.0571(4) Uani 1 1 d . . .
C5 C 0.30207(17) 0.84203(13) 0.30282(14) 0.0528(4) Uani 1 1 d . . .
C6 C 0.2892(2) 0.78522(16) 0.38188(16) 0.0701(5) Uani 1 1 d . . .
H6 H 0.2182 0.7454 0.3859 0.084 Uiso 1 1 calc R . .
C7 C 0.3970(2) 0.79786(16) 0.45125(16) 0.0709(6) Uani 1 1 d . . .
H7 H 0.4126 0.7698 0.5115 0.085 Uiso 1 1 calc R . .
C8 C 0.48050(18) 0.86112(14) 0.41523(13) 0.0557(4) Uani 1 1 d . . .
C9 C 0.60296(19) 0.89175(15) 0.45332(14) 0.0609(5) Uani 1 1 d . . .
H9 H 0.6384 0.8750 0.5165 0.073 Uiso 1 1 calc R . .
C10 C 0.67620(17) 0.94574(15) 0.40351(13) 0.0552(4) Uani 1 1 d . . .
C11 C 0.80236(19) 0.97693(18) 0.42849(16) 0.0722(6) Uani 1 1 d . . .
H11 H 0.8568 0.9668 0.4870 0.087 Uiso 1 1 calc R . .
C12 C 0.83120(17) 1.02483(18) 0.35173(16) 0.0693(5) Uani 1 1 d . . .
H12 H 0.9092 1.0531 0.3486 0.083 Uiso 1 1 calc R . .
C13 C 0.72276(15) 1.02429(14) 0.27789(13) 0.0509(4) Uani 1 1 d . . .
C14 C 0.71697(16) 1.06545(15) 0.17756(14) 0.0565(4) Uani 1 1 d . . .
C15 C 0.6160(2) 1.14999(18) 0.16602(18) 0.0750(6) Uani 1 1 d . . .
H15A H 0.5361 1.1133 0.1584 0.112 Uiso 1 1 calc R . .
H15B H 0.6209 1.1778 0.1045 0.112 Uiso 1 1 calc R . .
H15C H 0.6274 1.2120 0.2279 0.112 Uiso 1 1 calc R . .
C16 C 0.6977(2) 0.9635(2) 0.08130(16) 0.0800(6) Uani 1 1 d . . .
H16A H 0.7637 0.9125 0.0882 0.120 Uiso 1 1 calc R . .
H16B H 0.6977 0.9890 0.0179 0.120 Uiso 1 1 calc R . .
H16C H 0.6198 0.9251 0.0776 0.120 Uiso 1 1 calc R . .
C17 C 0.8416(2) 1.1254(2) 0.1791(2) 0.0935(7) Uani 1 1 d . . .
H17A H 0.8581 1.1876 0.2406 0.140 Uiso 1 1 calc R . .
H17B H 0.8375 1.1532 0.1164 0.140 Uiso 1 1 calc R . .
H17C H 0.9068 1.0728 0.1810 0.140 Uiso 1 1 calc R . .
C18 C 0.7621(2) 0.6558(2) 0.1851(2) 0.0834(6) Uani 1 1 d . . .
H18A H 0.7777 0.7130 0.2505 0.125 Uiso 1 1 calc R . .
H18B H 0.7305 0.6899 0.1283 0.125 Uiso 1 1 calc R . .
H18C H 0.8380 0.6198 0.1714 0.125 Uiso 1 1 calc R . .
C19 C 0.6467(2) 0.4708(2) 0.09294(16) 0.0819(7) Uani 1 1 d . . .
H19A H 0.7224 0.4320 0.0857 0.123 Uiso 1 1 calc R . .
H19B H 0.6213 0.5006 0.0321 0.123 Uiso 1 1 calc R . .
H19C H 0.5832 0.4190 0.0983 0.123 Uiso 1 1 calc R . .
C20 C 0.5428(2) 0.6262(2) 0.2000(2) 0.0960(8) Uani 1 1 d . . .
H20A H 0.4791 0.5711 0.1979 0.144 Uiso 1 1 calc R . .
H20B H 0.5219 0.6602 0.1413 0.144 Uiso 1 1 calc R . .
H20C H 0.5497 0.6836 0.2652 0.144 Uiso 1 1 calc R . .
C21 C 0.66753(16) 0.56812(16) 0.19305(15) 0.0619(5) Uani 1 1 d . . .
C22 C 0.70363(17) 0.52064(15) 0.28848(14) 0.0597(5) Uani 1 1 d . . .
C23 C 0.6277(2) 0.5156(2) 0.36450(19) 0.0860(7) Uani 1 1 d . . .
H23 H 0.5486 0.5434 0.3651 0.103 Uiso 1 1 calc R . .
C24 C 0.6889(3) 0.4637(2) 0.4366(2) 0.0938(8) Uani 1 1 d . . .
H24 H 0.6597 0.4500 0.4951 0.113 Uiso 1 1 calc R . .
C25 C 0.8046(2) 0.43436(17) 0.40641(15) 0.0735(4) Uani 1 1 d U . .
C26 C 0.9000(2) 0.37844(17) 0.45043(15) 0.0760(4) Uani 1 1 d U . .
H26 H 0.8921 0.3575 0.5125 0.091 Uiso 1 1 calc R . .
C27 C 1.0059(2) 0.35172(17) 0.40837(15) 0.0738(4) Uani 1 1 d U . .
C28 C 1.1071(3) 0.28876(19) 0.4389(2) 0.0959(9) Uani 1 1 d . . .
H28 H 1.1189 0.2586 0.4980 0.115 Uiso 1 1 calc R . .
C29 C 1.1840(3) 0.28015(19) 0.3668(2) 0.0905(8) Uani 1 1 d . . .
H29 H 1.2576 0.2418 0.3674 0.109 Uiso 1 1 calc R . .
C30 C 1.13477(18) 0.33881(15) 0.29038(17) 0.0656(5) Uani 1 1 d . . .
C31 C 1.19143(17) 0.34571(17) 0.19470(19) 0.0709(6) Uani 1 1 d . . .
C32 C 1.1153(2) 0.2688(2) 0.09510(19) 0.0871(7) Uani 1 1 d . . .
H32A H 1.1139 0.1924 0.1027 0.131 Uiso 1 1 calc R . .
H32B H 1.1522 0.2716 0.0343 0.131 Uiso 1 1 calc R . .
H32C H 1.0320 0.2941 0.0860 0.131 Uiso 1 1 calc R . .
C33 C 1.3241(2) 0.3026(2) 0.2057(3) 0.1183(11) Uani 1 1 d . . .
H33A H 1.3728 0.3467 0.2697 0.177 Uiso 1 1 calc R . .
H33B H 1.3609 0.3095 0.1459 0.177 Uiso 1 1 calc R . .
H33C H 1.3214 0.2246 0.2083 0.177 Uiso 1 1 calc R . .
C34 C 1.2019(2) 0.46705(18) 0.1827(2) 0.0820(6) Uani 1 1 d . . .
H34A H 1.1203 0.4938 0.1659 0.123 Uiso 1 1 calc R . .
H34B H 1.2479 0.4685 0.1267 0.123 Uiso 1 1 calc R . .
H34C H 1.2439 0.5149 0.2478 0.123 Uiso 1 1 calc R . .


_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 F2 1.367(2) . ?
B1 F1 1.389(2) . ?
B1 N2 1.570(2) . ?
B1 N1 1.572(2) . ?
C1 C3 1.531(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N1 C5 1.363(2) . ?
N1 C8 1.396(2) . ?
B2 F3 1.364(2) . ?
B2 F4 1.388(2) . ?
B2 N4 1.569(2) . ?
B2 N3 1.572(2) . ?
C2 C3 1.535(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N2 C13 1.363(2) . ?
N2 C10 1.399(2) . ?
C3 C5 1.519(3) . ?
C3 C4 1.541(3) . ?
N3 C22 1.371(2) . ?
N3 C25 1.393(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
N4 C30 1.370(3) . ?
N4 C27 1.393(2) . ?
C5 C6 1.408(2) . ?
C6 C7 1.355(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.402(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(3) . ?
C9 C10 1.371(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(3) . ?
C11 C12 1.360(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.408(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.517(2) . ?
C14 C15 1.526(3) . ?
C14 C16 1.534(3) . ?
C14 C17 1.540(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C21 1.520(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.532(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.542(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.506(3) . ?
C22 C23 1.410(3) . ?
C23 C24 1.357(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.404(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(3) . ?
C26 C27 1.367(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.409(3) . ?
C28 C29 1.351(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.412(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.510(3) . ?
C31 C34 1.531(3) . ?
C31 C32 1.534(3) . ?
C31 C33 1.540(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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
F2 B1 F1 111.28(13) . . ?
F2 B1 N2 110.48(13) . . ?
F1 B1 N2 107.95(13) . . ?
F2 B1 N1 109.90(14) . . ?
F1 B1 N1 107.91(13) . . ?
N2 B1 N1 109.26(12) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 N1 C8 107.75(14) . . ?
C5 N1 B1 131.29(13) . . ?
C8 N1 B1 120.55(14) . . ?
F3 B2 F4 111.42(14) . . ?
F3 B2 N4 110.01(15) . . ?
F4 B2 N4 107.88(13) . . ?
F3 B2 N3 110.37(14) . . ?
F4 B2 N3 107.74(15) . . ?
N4 B2 N3 109.35(14) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C13 N2 C10 107.37(14) . . ?
C13 N2 B1 131.12(13) . . ?
C10 N2 B1 120.56(13) . . ?
C5 C3 C1 113.24(15) . . ?
C5 C3 C2 109.03(15) . . ?
C1 C3 C2 110.52(17) . . ?
C5 C3 C4 109.32(16) . . ?
C1 C3 C4 106.85(16) . . ?
C2 C3 C4 107.72(17) . . ?
C22 N3 C25 107.78(16) . . ?
C22 N3 B2 130.67(14) . . ?
C25 N3 B2 120.68(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C30 N4 C27 108.13(16) . . ?
C30 N4 B2 130.81(15) . . ?
C27 N4 B2 120.42(17) . . ?
N1 C5 C6 107.83(17) . . ?
N1 C5 C3 127.17(14) . . ?
C6 C5 C3 124.96(17) . . ?
C7 C6 C5 109.01(18) . . ?
C7 C6 H6 125.5 . . ?
C5 C6 H6 125.5 . . ?
C6 C7 C8 107.20(17) . . ?
C6 C7 H7 126.4 . . ?
C8 C7 H7 126.4 . . ?
C9 C8 N1 121.28(15) . . ?
C9 C8 C7 130.47(17) . . ?
N1 C8 C7 108.19(17) . . ?
C10 C9 C8 123.65(16) . . ?
C10 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
C9 C10 C11 130.63(17) . . ?
C9 C10 N2 121.00(16) . . ?
C11 C10 N2 108.34(16) . . ?
C12 C11 C10 107.59(16) . . ?
C12 C11 H11 126.2 . . ?
C10 C11 H11 126.2 . . ?
C11 C12 C13 108.33(18) . . ?
C11 C12 H12 125.8 . . ?
C13 C12 H12 125.8 . . ?
N2 C13 C12 108.37(16) . . ?
N2 C13 C14 126.80(14) . . ?
C12 C13 C14 124.76(16) . . ?
C13 C14 C15 113.00(15) . . ?
C13 C14 C16 109.27(15) . . ?
C15 C14 C16 110.35(17) . . ?
C13 C14 C17 109.28(16) . . ?
C15 C14 C17 107.19(17) . . ?
C16 C14 C17 107.59(17) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 H18A 109.5 . . ?
C21 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C21 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 H19A 109.5 . . ?
C21 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C21 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C18 112.69(16) . . ?
C22 C21 C19 109.22(16) . . ?
C18 C21 C19 111.15(18) . . ?
C22 C21 C20 109.36(17) . . ?
C18 C21 C20 107.49(18) . . ?
C19 C21 C20 106.75(16) . . ?
N3 C22 C23 107.65(19) . . ?
N3 C22 C21 126.88(15) . . ?
C23 C22 C21 125.4(2) . . ?
C24 C23 C22 109.0(2) . . ?
C24 C23 H23 125.5 . . ?
C22 C23 H23 125.5 . . ?
C23 C24 C25 107.3(2) . . ?
C23 C24 H24 126.3 . . ?
C25 C24 H24 126.3 . . ?
C26 C25 N3 120.8(2) . . ?
C26 C25 C24 130.9(2) . . ?
N3 C25 C24 108.3(2) . . ?
C27 C26 C25 123.86(19) . . ?
C27 C26 H26 118.1 . . ?
C25 C26 H26 118.1 . . ?
C26 C27 N4 121.2(2) . . ?
C26 C27 C28 130.8(2) . . ?
N4 C27 C28 107.8(2) . . ?
C29 C28 C27 107.6(2) . . ?
C29 C28 H28 126.2 . . ?
C27 C28 H28 126.2 . . ?
C28 C29 C30 109.0(2) . . ?
C28 C29 H29 125.5 . . ?
C30 C29 H29 125.5 . . ?
N4 C30 C29 107.5(2) . . ?
N4 C30 C31 127.31(16) . . ?
C29 C30 C31 125.1(2) . . ?
C30 C31 C34 112.57(18) . . ?
C30 C31 C32 109.29(16) . . ?
C34 C31 C32 110.86(19) . . ?
C30 C31 C33 109.7(2) . . ?
C34 C31 C33 106.65(17) . . ?
C32 C31 C33 107.7(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_131106b
_database_code_depnum_ccdc_archive 'CCDC 995009'
_audit_update_record             
;
2014-04-02 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;
_audit_creation_date             2013-11-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C12 H13 B F2 N2)'
_chemical_formula_sum            'C24 H26 B2 F4 N4'
_chemical_formula_weight         468.11
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   16.054(2)
_cell_length_b                   12.6204(19)
_cell_length_c                   13.685(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.2280(10)
_cell_angle_gamma                90.00
_cell_volume                     2395.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4092
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.69
_cell_measurement_theta_min      2.28
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9286
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.18
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3418
_reflns_number_total             4704
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_coef       0.0077(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.3109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0987
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1DA-C1CA
 1.54 with sigma of 0.02
 C1CA-C1EA
 1.54 with sigma of 0.02
 C18A-C17A
 1.54 with sigma of 0.02
 C18A-C14A
 1.54 with sigma of 0.02
 C1CB-C1EB
 1.54 with sigma of 0.02
 C1CB-C1DB
 1.54 with sigma of 0.02
 C18B-C14B
 1.54 with sigma of 0.02
 C17B-C18B
 1.54 with sigma of 0.02
3. Others
 Sof(C14B)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C17B)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=Sof(C18B)=Sof(H18B)=1-FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C14A)=
 Sof(H14D)=Sof(H14E)=Sof(H14F)=FVAR(1)
 Sof(C1CB)=Sof(H1CB)=Sof(C1DB)=Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=Sof(C1EB)=
 Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=1-FVAR(2)
 Sof(C1CA)=Sof(H1CA)=Sof(C1DA)=Sof(H1DD)=Sof(H1DE)=Sof(H1DF)=Sof(C1EA)=
 Sof(H1ED)=Sof(H1EE)=Sof(H1EF)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C1CB(H1CB), C18B(H18B), C18A(H18A), C1CA(H1CA)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C7(H7), C8(H8), C15(H15), C11(H11), C13(H13), C16(H16),
 C19(H19), C10(H10), C1A(H1A), C1B(H1B)
4.c Idealised Me refined as rotating group:
 C1DB(H1DA,H1DB,H1DC), C1EB(H1EA,H1EB,H1EC), C14B(H14A,H14B,H14C), C17B(H17A,
 H17B,H17C), C17A(H17D,H17E,H17F), C14A(H14D,H14E,H14F), C1DA(H1DD,H1DE,H1DF),
 C1EA(H1ED,H1EE,H1EF)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
F3 F 0.61036(12) 0.63499(11) 0.45341(14) 0.1087(5) Uani 1 1 d . . .
C5 C 0.33392(17) 0.42325(18) 0.37821(18) 0.0810(6) Uani 1 1 d . B .
H5 H 0.3779 0.4788 0.4049 0.097 Uiso 1 1 calc R . .
C6 C 0.24937(15) 0.28544(18) 0.27993(18) 0.0736(6) Uani 1 1 d . B .
F9 F 0.48885(14) 0.62374(11) 0.48869(15) 0.1148(6) Uani 1 1 d . . .
C2 C 0.22080(15) 0.20430(18) 0.19968(19) 0.0794(6) Uani 1 1 d . . .
C1 C 0.6431(2) 0.9284(2) 0.6513(2) 0.0955(7) Uani 1 1 d . . .
H1 H 0.6522 1.0004 0.6677 0.115 Uiso 1 1 calc R . .
N4 N 0.31952(11) 0.35816(13) 0.29421(13) 0.0671(4) Uani 1 1 d . . .
C3 C 0.58305(17) 0.88444(15) 0.5440(2) 0.0751(6) Uani 1 1 d . A .
C7 C 0.2738(2) 0.3963(2) 0.4203(2) 0.0971(7) Uani 1 1 d . . .
H7 H 0.2704 0.4296 0.4788 0.116 Uiso 1 1 calc R B .
C9 C 0.47056(18) 0.86344(17) 0.3450(2) 0.0794(6) Uani 1 1 d . A .
C12 C 0.52324(18) 0.92924(17) 0.4385(2) 0.0785(6) Uani 1 1 d . . .
F14 F 0.35064(14) 0.45569(11) 0.16643(14) 0.1127(5) Uani 1 1 d . . .
N3 N 0.47743(14) 0.75428(14) 0.35548(17) 0.0814(5) Uani 1 1 d . . .
C8 C 0.6857(3) 0.8492(2) 0.7270(3) 0.1166(10) Uani 1 1 d . . .
H8 H 0.7287 0.8563 0.8042 0.140 Uiso 1 1 calc R . .
C4 C 0.26257(17) 0.19690(16) 0.13149(19) 0.0793(6) Uani 1 1 d . B .
N10 N 0.59176(14) 0.77464(13) 0.55740(16) 0.0774(5) Uani 1 1 d . . .
C15 C 0.6530(2) 0.7558(2) 0.6674(3) 0.1077(9) Uani 1 1 d . A .
H15 H 0.6711 0.6886 0.6993 0.129 Uiso 1 1 calc R . .
B1 B 0.5425(2) 0.6920(2) 0.4641(3) 0.0789(7) Uani 1 1 d . A .
C11 C 0.4185(2) 0.7133(3) 0.2530(3) 0.1097(9) Uani 1 1 d . A .
H11 H 0.4097 0.6414 0.2363 0.132 Uiso 1 1 calc R . .
C13 C 0.4044(2) 0.8866(3) 0.2312(3) 0.1063(8) Uani 1 1 d . . .
H13 H 0.3857 0.9538 0.1996 0.128 Uiso 1 1 calc R A .
C16 C 0.3728(3) 0.7933(3) 0.1761(3) 0.1307(11) Uani 1 1 d . A .
H16 H 0.3280 0.7848 0.0997 0.157 Uiso 1 1 calc R . .
F17 F 0.46918(11) 0.35347(15) 0.29620(15) 0.1211(6) Uani 1 1 d . . .
B18 B 0.3710(2) 0.36259(19) 0.2257(2) 0.0760(6) Uani 1 1 d . B .
C19 C 0.22118(19) 0.3114(2) 0.3591(2) 0.0922(7) Uani 1 1 d . B .
H19 H 0.1744 0.2765 0.3680 0.111 Uiso 1 1 calc R . .
N1 N 0.33276(13) 0.26854(14) 0.14417(16) 0.0789(5) Uani 1 1 d . . .
C10 C 0.3592(3) 0.2432(3) 0.0685(3) 0.1137(9) Uani 1 1 d . B .
H10 H 0.4053 0.2791 0.0592 0.136 Uiso 1 1 calc R . .
C1A C 0.3084(3) 0.1571(3) 0.0070(3) 0.1350(12) Uani 1 1 d . . .
H1A H 0.3142 0.1249 -0.0504 0.162 Uiso 1 1 calc R B .
C1B C 0.2482(2) 0.1267(2) 0.0441(3) 0.1107(10) Uani 1 1 d . B .
H1B H 0.2053 0.0701 0.0171 0.133 Uiso 1 1 calc R . .
C1CB C 0.5053(8) 1.0406(9) 0.4123(12) 0.093(2) Uani 0.62(2) 1 d PD A 2
H1CB H 0.4612 1.0421 0.3303 0.111 Uiso 0.62(2) 1 calc PR A 2
C1DB C 0.5922(11) 1.0990(7) 0.4282(16) 0.128(4) Uani 0.62(2) 1 d PD A 2
H1DA H 0.6433 1.0920 0.5053 0.192 Uiso 0.62(2) 1 calc PR A 2
H1DB H 0.5766 1.1726 0.4108 0.192 Uiso 0.62(2) 1 calc PR A 2
H1DC H 0.6126 1.0699 0.3788 0.192 Uiso 0.62(2) 1 calc PR A 2
C1EB C 0.4553(9) 1.0959(6) 0.4564(16) 0.174(6) Uani 0.62(2) 1 d PD A 2
H1EA H 0.3944 1.0621 0.4321 0.261 Uiso 0.62(2) 1 calc PR A 2
H1EB H 0.4447 1.1677 0.4297 0.261 Uiso 0.62(2) 1 calc PR A 2
H1EC H 0.4927 1.0955 0.5375 0.261 Uiso 0.62(2) 1 calc PR A 2
C14B C 0.1904(19) 0.0342(15) 0.254(2) 0.151(9) Uani 0.432(15) 1 d PD B 2
H14A H 0.2185 0.0108 0.2106 0.227 Uiso 0.432(15) 1 calc PR B 2
H14B H 0.1441 -0.0170 0.2490 0.227 Uiso 0.432(15) 1 calc PR B 2
H14C H 0.2401 0.0421 0.3320 0.227 Uiso 0.432(15) 1 calc PR B 2
C17B C 0.0542(14) 0.1245(19) 0.0950(18) 0.152(9) Uani 0.432(15) 1 d PD B 2
H17A H 0.0317 0.1908 0.0559 0.227 Uiso 0.432(15) 1 calc PR B 2
H17B H 0.0039 0.0922 0.1032 0.227 Uiso 0.432(15) 1 calc PR B 2
H17C H 0.0716 0.0784 0.0524 0.227 Uiso 0.432(15) 1 calc PR B 2
C18B C 0.1392(5) 0.1433(6) 0.2079(8) 0.069(2) Uani 0.432(15) 1 d PD B 2
H18B H 0.1222 0.1779 0.2595 0.083 Uiso 0.432(15) 1 calc PR B 2
C18A C 0.1523(4) 0.1096(7) 0.1742(7) 0.084(2) Uani 0.568(15) 1 d PD B 1
H18A H 0.1544 0.0670 0.1156 0.100 Uiso 0.568(15) 1 calc PR B 1
C17A C 0.0518(7) 0.1528(13) 0.1241(16) 0.138(5) Uani 0.568(15) 1 d PD B 1
H17D H 0.0492 0.2020 0.1760 0.208 Uiso 0.568(15) 1 calc PR B 1
H17E H 0.0076 0.0957 0.1099 0.208 Uiso 0.568(15) 1 calc PR B 1
H17F H 0.0343 0.1883 0.0543 0.208 Uiso 0.568(15) 1 calc PR B 1
C14A C 0.1814(10) 0.0379(9) 0.2751(10) 0.083(2) Uani 0.568(15) 1 d PD B 1
H14D H 0.2352 -0.0049 0.2874 0.125 Uiso 0.568(15) 1 calc PR B 1
H14E H 0.1282 -0.0071 0.2608 0.125 Uiso 0.568(15) 1 calc PR B 1
H14F H 0.1991 0.0802 0.3411 0.125 Uiso 0.568(15) 1 calc PR B 1
C1CA C 0.5222(18) 1.0605(14) 0.445(2) 0.105(5) Uani 0.38(2) 1 d PD A 1
H1CA H 0.5800 1.0649 0.5204 0.126 Uiso 0.38(2) 1 calc PR A 1
C1DA C 0.572(2) 1.1029(18) 0.382(3) 0.182(14) Uani 0.38(2) 1 d PD A 1
H1DD H 0.5991 1.1716 0.4104 0.273 Uiso 0.38(2) 1 calc PR A 1
H1DE H 0.5260 1.1081 0.3024 0.273 Uiso 0.38(2) 1 calc PR A 1
H1DF H 0.6229 1.0552 0.3927 0.273 Uiso 0.38(2) 1 calc PR A 1
C1EA C 0.4537(13) 1.0995(16) 0.4842(15) 0.143(7) Uani 0.38(2) 1 d PD A 1
H1ED H 0.3932 1.0630 0.4429 0.214 Uiso 0.38(2) 1 calc PR A 1
H1EE H 0.4434 1.1743 0.4706 0.214 Uiso 0.38(2) 1 calc PR A 1
H1EF H 0.4813 1.0858 0.5636 0.214 Uiso 0.38(2) 1 calc PR A 1


_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
F3 B1 1.374(3) . ?
C5 H5 0.9300 . ?
C5 N4 1.335(3) . ?
C5 C7 1.393(4) . ?
C6 C2 1.399(3) . ?
C6 N4 1.388(3) . ?
C6 C19 1.407(3) . ?
F9 B1 1.374(3) . ?
C2 C4 1.400(4) . ?
C2 C18B 1.571(8) . ?
C2 C18A 1.541(7) . ?
C1 H1 0.9300 . ?
C1 C3 1.403(3) . ?
C1 C8 1.352(4) . ?
N4 B18 1.531(3) . ?
C3 C12 1.389(3) . ?
C3 N10 1.396(3) . ?
C7 H7 0.9300 . ?
C7 C19 1.360(4) . ?
C9 C12 1.398(3) . ?
C9 N3 1.384(3) . ?
C9 C13 1.405(4) . ?
C12 C1CB 1.443(12) . ?
C12 C1CA 1.660(18) . ?
F14 B18 1.371(3) . ?
N3 B1 1.535(4) . ?
N3 C11 1.339(3) . ?
C8 H8 0.9300 . ?
C8 C15 1.378(4) . ?
C4 N1 1.386(3) . ?
C4 C1B 1.410(4) . ?
N10 C15 1.342(3) . ?
N10 B1 1.525(3) . ?
C15 H15 0.9300 . ?
C11 H11 0.9300 . ?
C11 C16 1.373(5) . ?
C13 H13 0.9300 . ?
C13 C16 1.352(4) . ?
C16 H16 0.9300 . ?
F17 B18 1.378(3) . ?
B18 N1 1.530(3) . ?
C19 H19 0.9300 . ?
N1 C10 1.340(3) . ?
C10 H10 0.9300 . ?
C10 C1A 1.365(5) . ?
C1A H1A 0.9300 . ?
C1A C1B 1.354(5) . ?
C1B H1B 0.9300 . ?
C1CB H1CB 0.9800 . ?
C1CB C1DB 1.493(12) . ?
C1CB C1EB 1.409(11) . ?
C1DB H1DA 0.9600 . ?
C1DB H1DB 0.9600 . ?
C1DB H1DC 0.9600 . ?
C1EB H1EA 0.9600 . ?
C1EB H1EB 0.9600 . ?
C1EB H1EC 0.9600 . ?
C14B H14A 0.9600 . ?
C14B H14B 0.9600 . ?
C14B H14C 0.9600 . ?
C14B C18B 1.564(16) . ?
C17B H17A 0.9600 . ?
C17B H17B 0.9600 . ?
C17B H17C 0.9600 . ?
C17B C18B 1.478(17) . ?
C18B H18B 0.9800 . ?
C18A H18A 0.9800 . ?
C18A C17A 1.503(14) . ?
C18A C14A 1.515(11) . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C1CA H1CA 0.9800 . ?
C1CA C1DA 1.549(18) . ?
C1CA C1EA 1.525(17) . ?
C1DA H1DD 0.9600 . ?
C1DA H1DE 0.9600 . ?
C1DA H1DF 0.9600 . ?
C1EA H1ED 0.9600 . ?
C1EA H1EE 0.9600 . ?
C1EA H1EF 0.9600 . ?

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
N4 C5 H5 124.7 . . ?
N4 C5 C7 110.5(2) . . ?
C7 C5 H5 124.7 . . ?
C2 C6 C19 132.0(2) . . ?
N4 C6 C2 121.1(2) . . ?
N4 C6 C19 106.9(2) . . ?
C6 C2 C4 119.63(19) . . ?
C6 C2 C18B 105.0(5) . . ?
C6 C2 C18A 131.3(5) . . ?
C4 C2 C18B 135.3(5) . . ?
C4 C2 C18A 108.9(5) . . ?
C18A C2 C18B 27.1(2) . . ?
C3 C1 H1 125.5 . . ?
C8 C1 H1 125.5 . . ?
C8 C1 C3 109.0(2) . . ?
C5 N4 C6 107.73(19) . . ?
C5 N4 B18 126.29(19) . . ?
C6 N4 B18 125.98(18) . . ?
C12 C3 C1 132.7(2) . . ?
C12 C3 N10 120.80(19) . . ?
N10 C3 C1 106.5(2) . . ?
C5 C7 H7 126.8 . . ?
C19 C7 C5 106.4(2) . . ?
C19 C7 H7 126.8 . . ?
C12 C9 C13 131.5(2) . . ?
N3 C9 C12 121.1(2) . . ?
N3 C9 C13 107.4(2) . . ?
C3 C12 C9 119.5(2) . . ?
C3 C12 C1CB 127.0(6) . . ?
C3 C12 C1CA 111.7(9) . . ?
C9 C12 C1CB 113.4(6) . . ?
C9 C12 C1CA 128.7(9) . . ?
C1CB C12 C1CA 15.3(9) . . ?
C9 N3 B1 126.2(2) . . ?
C11 N3 C9 107.3(2) . . ?
C11 N3 B1 126.5(2) . . ?
C1 C8 H8 126.8 . . ?
C1 C8 C15 106.5(3) . . ?
C15 C8 H8 126.8 . . ?
C2 C4 C1B 132.7(2) . . ?
N1 C4 C2 120.4(2) . . ?
N1 C4 C1B 107.0(2) . . ?
C3 N10 B1 126.4(2) . . ?
C15 N10 C3 106.96(19) . . ?
C15 N10 B1 126.6(2) . . ?
C8 C15 H15 124.5 . . ?
N10 C15 C8 111.0(2) . . ?
N10 C15 H15 124.5 . . ?
F3 B1 F9 109.0(2) . . ?
F3 B1 N3 110.8(2) . . ?
F3 B1 N10 110.0(2) . . ?
F9 B1 N3 110.7(2) . . ?
F9 B1 N10 110.4(2) . . ?
N10 B1 N3 105.90(18) . . ?
N3 C11 H11 125.0 . . ?
N3 C11 C16 110.0(3) . . ?
C16 C11 H11 125.0 . . ?
C9 C13 H13 126.3 . . ?
C16 C13 C9 107.4(3) . . ?
C16 C13 H13 126.3 . . ?
C11 C16 H16 126.0 . . ?
C13 C16 C11 107.9(3) . . ?
C13 C16 H16 126.0 . . ?
F14 B18 N4 110.7(2) . . ?
F14 B18 F17 109.5(2) . . ?
F14 B18 N1 110.2(2) . . ?
F17 B18 N4 110.4(2) . . ?
F17 B18 N1 110.0(2) . . ?
N1 B18 N4 106.06(17) . . ?
C6 C19 H19 125.8 . . ?
C7 C19 C6 108.5(2) . . ?
C7 C19 H19 125.8 . . ?
C4 N1 B18 126.82(19) . . ?
C10 N1 C4 107.5(2) . . ?
C10 N1 B18 125.6(2) . . ?
N1 C10 H10 125.0 . . ?
N1 C10 C1A 110.1(3) . . ?
C1A C10 H10 125.0 . . ?
C10 C1A H1A 125.9 . . ?
C1B C1A C10 108.2(3) . . ?
C1B C1A H1A 125.9 . . ?
C4 C1B H1B 126.4 . . ?
C1A C1B C4 107.3(3) . . ?
C1A C1B H1B 126.4 . . ?
C12 C1CB H1CB 104.0 . . ?
C12 C1CB C1DB 112.9(8) . . ?
C1DB C1CB H1CB 104.0 . . ?
C1EB C1CB C12 117.4(9) . . ?
C1EB C1CB H1CB 104.0 . . ?
C1EB C1CB C1DB 112.7(12) . . ?
C1CB C1DB H1DA 109.5 . . ?
C1CB C1DB H1DB 109.5 . . ?
C1CB C1DB H1DC 109.5 . . ?
H1DA C1DB H1DB 109.5 . . ?
H1DA C1DB H1DC 109.5 . . ?
H1DB C1DB H1DC 109.5 . . ?
C1CB C1EB H1EA 109.5 . . ?
C1CB C1EB H1EB 109.5 . . ?
C1CB C1EB H1EC 109.5 . . ?
H1EA C1EB H1EB 109.5 . . ?
H1EA C1EB H1EC 109.5 . . ?
H1EB C1EB H1EC 109.5 . . ?
H14A C14B H14B 109.5 . . ?
H14A C14B H14C 109.5 . . ?
H14B C14B H14C 109.5 . . ?
C18B C14B H14A 109.5 . . ?
C18B C14B H14B 109.5 . . ?
C18B C14B H14C 109.5 . . ?
H17A C17B H17B 109.5 . . ?
H17A C17B H17C 109.5 . . ?
H17B C17B H17C 109.5 . . ?
C18B C17B H17A 109.5 . . ?
C18B C17B H17B 109.5 . . ?
C18B C17B H17C 109.5 . . ?
C2 C18B H18B 112.3 . . ?
C14B C18B C2 100.0(12) . . ?
C14B C18B H18B 112.3 . . ?
C17B C18B C2 111.6(12) . . ?
C17B C18B C14B 107.7(17) . . ?
C17B C18B H18B 112.3 . . ?
C2 C18A H18A 107.2 . . ?
C17A C18A C2 107.6(9) . . ?
C17A C18A H18A 107.2 . . ?
C17A C18A C14A 113.6(11) . . ?
C14A C18A C2 113.6(7) . . ?
C14A C18A H18A 107.2 . . ?
C12 C1CA H1CA 94.8 . . ?
C1DA C1CA C12 106.9(13) . . ?
C1DA C1CA H1CA 94.8 . . ?
C1EA C1CA C12 111.8(13) . . ?
C1EA C1CA H1CA 94.8 . . ?
C1EA C1CA C1DA 139.0(19) . . ?

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
C5 N4 B18 F14 -63.2(3) . . . . ?
C5 N4 B18 F17 58.2(3) . . . . ?
C5 N4 B18 N1 177.35(17) . . . . ?
C5 C7 C19 C6 0.5(3) . . . . ?
C6 C2 C4 N1 0.9(3) . . . . ?
C6 C2 C4 C1B -179.0(2) . . . . ?
C6 C2 C18B C14B -113.7(13) . . . . ?
C6 C2 C18B C17B 132.6(13) . . . . ?
C6 C2 C18A C17A 69.2(11) . . . . ?
C6 C2 C18A C14A -57.4(10) . . . . ?
C6 N4 B18 F14 116.8(2) . . . . ?
C6 N4 B18 F17 -121.8(2) . . . . ?
C6 N4 B18 N1 -2.6(3) . . . . ?
C2 C6 N4 C5 -177.98(19) . . . . ?
C2 C6 N4 B18 2.0(3) . . . . ?
C2 C6 C19 C7 177.8(2) . . . . ?
C2 C4 N1 B18 -2.1(3) . . . . ?
C2 C4 N1 C10 -179.7(2) . . . . ?
C2 C4 C1B C1A 179.7(3) . . . . ?
C1 C3 C12 C9 -179.6(2) . . . . ?
C1 C3 C12 C1CB -1.7(7) . . . . ?
C1 C3 C12 C1CA -2.2(8) . . . . ?
C1 C3 N10 C15 0.7(3) . . . . ?
C1 C3 N10 B1 -178.1(2) . . . . ?
C1 C8 C15 N10 0.1(4) . . . . ?
N4 C5 C7 C19 0.0(3) . . . . ?
N4 C6 C2 C4 -0.8(3) . . . . ?
N4 C6 C2 C18B -178.2(3) . . . . ?
N4 C6 C2 C18A 174.1(4) . . . . ?
N4 C6 C19 C7 -0.9(3) . . . . ?
N4 B18 N1 C4 2.7(3) . . . . ?
N4 B18 N1 C10 179.9(2) . . . . ?
C3 C1 C8 C15 0.4(4) . . . . ?
C3 C12 C1CB C1DB 66.6(14) . . . . ?
C3 C12 C1CB C1EB -67.1(10) . . . . ?
C3 C12 C1CA C1DA 112(2) . . . . ?
C3 C12 C1CA C1EA -81.6(17) . . . . ?
C3 N10 C15 C8 -0.5(3) . . . . ?
C3 N10 B1 F3 116.3(3) . . . . ?
C3 N10 B1 F9 -123.3(3) . . . . ?
C3 N10 B1 N3 -3.4(3) . . . . ?
C7 C5 N4 C6 -0.6(2) . . . . ?
C7 C5 N4 B18 179.4(2) . . . . ?
C9 C12 C1CB C1DB -115.4(13) . . . . ?
C9 C12 C1CB C1EB 110.9(9) . . . . ?
C9 C12 C1CA C1DA -71(3) . . . . ?
C9 C12 C1CA C1EA 95.5(15) . . . . ?
C9 N3 B1 F3 -115.7(2) . . . . ?
C9 N3 B1 F9 123.2(2) . . . . ?
C9 N3 B1 N10 3.6(3) . . . . ?
C9 N3 C11 C16 -0.4(3) . . . . ?
C9 C13 C16 C11 -0.5(4) . . . . ?
C12 C3 N10 C15 -179.4(2) . . . . ?
C12 C3 N10 B1 1.7(4) . . . . ?
C12 C9 N3 B1 -2.0(4) . . . . ?
C12 C9 N3 C11 179.3(2) . . . . ?
C12 C9 C13 C16 -178.8(3) . . . . ?
F14 B18 N1 C4 -117.1(2) . . . . ?
F14 B18 N1 C10 60.1(3) . . . . ?
N3 C9 C12 C3 -0.4(3) . . . . ?
N3 C9 C12 C1CB -178.6(5) . . . . ?
N3 C9 C12 C1CA -177.3(8) . . . . ?
N3 C9 C13 C16 0.2(3) . . . . ?
N3 C11 C16 C13 0.6(4) . . . . ?
C8 C1 C3 C12 179.4(3) . . . . ?
C8 C1 C3 N10 -0.7(3) . . . . ?
C4 C2 C18B C14B 69.6(13) . . . . ?
C4 C2 C18B C17B -44.1(14) . . . . ?
C4 C2 C18A C17A -115.4(12) . . . . ?
C4 C2 C18A C14A 118.0(8) . . . . ?
C4 N1 C10 C1A -0.1(3) . . . . ?
N10 C3 C12 C9 0.6(3) . . . . ?
N10 C3 C12 C1CB 178.5(5) . . . . ?
N10 C3 C12 C1CA 178.0(7) . . . . ?
C15 N10 B1 F3 -62.3(3) . . . . ?
C15 N10 B1 F9 58.1(4) . . . . ?
C15 N10 B1 N3 177.9(2) . . . . ?
B1 N3 C11 C16 -179.2(3) . . . . ?
B1 N10 C15 C8 178.4(3) . . . . ?
C11 N3 B1 F3 62.8(3) . . . . ?
C11 N3 B1 F9 -58.3(3) . . . . ?
C11 N3 B1 N10 -178.0(2) . . . . ?
C13 C9 C12 C3 178.5(3) . . . . ?
C13 C9 C12 C1CB 0.3(6) . . . . ?
C13 C9 C12 C1CA 1.6(9) . . . . ?
C13 C9 N3 B1 178.8(2) . . . . ?
C13 C9 N3 C11 0.1(3) . . . . ?
F17 B18 N1 C4 122.1(2) . . . . ?
F17 B18 N1 C10 -60.7(3) . . . . ?
B18 N1 C10 C1A -177.8(3) . . . . ?
C19 C6 C2 C4 -179.4(2) . . . . ?
C19 C6 C2 C18B 3.3(4) . . . . ?
C19 C6 C2 C18A -4.4(5) . . . . ?
C19 C6 N4 C5 0.9(2) . . . . ?
C19 C6 N4 B18 -179.13(19) . . . . ?
N1 C4 C1B C1A -0.1(3) . . . . ?
N1 C10 C1A C1B 0.0(4) . . . . ?
C10 C1A C1B C4 0.1(4) . . . . ?
C1B C4 N1 B18 177.8(2) . . . . ?
C1B C4 N1 C10 0.2(3) . . . . ?
C1CB C12 C1CA C1DA -66(4) . . . . ?
C1CB C12 C1CA C1EA 100(4) . . . . ?
C18B C2 C4 N1 177.2(4) . . . . ?
C18B C2 C4 C1B -2.6(6) . . . . ?
C18B C2 C18A C17A 52.8(15) . . . . ?
C18B C2 C18A C14A -73.9(11) . . . . ?
C18A C2 C4 N1 -175.2(3) . . . . ?
C18A C2 C4 C1B 5.0(4) . . . . ?
C18A C2 C18B C14B 53.6(14) . . . . ?
C18A C2 C18B C17B -60.1(16) . . . . ?
C1CA C12 C1CB C1DB 68(4) . . . . ?
C1CA C12 C1CB C1EB -65(4) . . . . ?

####################################################################### 
# 
# 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_101210a
_database_code_depnum_ccdc_archive 'CCDC 995010'
_audit_update_record             
;
2014-04-02 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 B F2 N2'
_chemical_formula_weight         248.08

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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                   14.254(2)
_cell_length_b                   13.5629(19)
_cell_length_c                   6.4554(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1248.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2269
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      20.69

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10436
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2786
_reflns_number_gt                1637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1693P)²+0.0282P] 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   3(2)
_refine_ls_number_reflns         2786
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2688
_refine_ls_wR_factor_gt          0.2216
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002

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
B1 B 0.2242(4) 0.9758(4) 0.0120(10) 0.0498(13) Uani 1 1 d . . .
C1 C 0.2754(3) 0.8759(3) -0.3045(10) 0.0561(12) Uani 1 1 d . . .
H1 H 0.3178 0.9225 -0.3533 0.067 Uiso 1 1 calc R . .
C2 C 0.2573(4) 0.7846(4) -0.3963(9) 0.0589(13) Uani 1 1 d . . .
H2 H 0.2846 0.7604 -0.5170 0.071 Uiso 1 1 calc R . .
C3 C 0.1916(4) 0.7369(4) -0.2752(9) 0.0537(12) Uani 1 1 d . . .
H3 H 0.1678 0.6740 -0.2979 0.064 Uiso 1 1 calc R . .
C4 C 0.1668(3) 0.8013(3) -0.1091(7) 0.0432(10) Uani 1 1 d . . .
C5 C 0.1017(3) 0.7931(3) 0.0562(6) 0.0433(10) Uani 1 1 d . . .
C6 C 0.0991(3) 0.8699(3) 0.2043(7) 0.0421(9) Uani 1 1 d . . .
C7 C 0.0470(3) 0.8831(4) 0.3896(8) 0.0540(11) Uani 1 1 d . . .
H7 H 0.0023 0.8398 0.4421 0.065 Uiso 1 1 calc R . .
C8 C 0.0738(4) 0.9706(4) 0.4779(10) 0.0660(15) Uani 1 1 d . . .
H8 H 0.0508 0.9978 0.6001 0.079 Uiso 1 1 calc R . .
C9 C 0.1415(4) 1.0105(4) 0.3500(9) 0.0551(13) Uani 1 1 d . . .
H9 H 0.1721 1.0699 0.3742 0.066 Uiso 1 1 calc R . .
C10 C 0.0335(4) 0.7056(3) 0.0737(8) 0.0537(12) Uani 1 1 d . . .
C11 C 0.0363(8) 0.6275(7) -0.0976(17) 0.136(4) Uani 1 1 d . . .
H11A H 0.0187 0.6571 -0.2271 0.203 Uiso 1 1 calc R . .
H11B H -0.0068 0.5754 -0.0647 0.203 Uiso 1 1 calc R . .
H11C H 0.0986 0.6012 -0.1085 0.203 Uiso 1 1 calc R . .
C12 C 0.0522(9) 0.6529(7) 0.2828(14) 0.124(4) Uani 1 1 d . . .
H12A H 0.1108 0.6182 0.2755 0.186 Uiso 1 1 calc R . .
H12B H 0.0025 0.6071 0.3104 0.186 Uiso 1 1 calc R . .
H12C H 0.0550 0.7009 0.3919 0.186 Uiso 1 1 calc R . .
C13 C -0.0648(5) 0.7443(5) 0.0773(17) 0.103(3) Uani 1 1 d . . .
H13A H -0.0651 0.8095 0.1356 0.155 Uiso 1 1 calc R . .
H13B H -0.1034 0.7017 0.1601 0.155 Uiso 1 1 calc R . .
H13C H -0.0890 0.7467 -0.0613 0.155 Uiso 1 1 calc R . .
F1 F 0.3141(2) 0.9920(2) 0.0837(6) 0.0741(11) Uani 1 1 d . . .
F2 F 0.1955(2) 1.05942(19) -0.0987(6) 0.0732(10) Uani 1 1 d . . .
N1 N 0.2219(2) 0.8856(3) -0.1349(7) 0.0449(9) Uani 1 1 d . . .
N2 N 0.1570(3) 0.9523(3) 0.1867(7) 0.0474(9) 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
B1 F1 1.380(6) . ?
B1 F2 1.401(7) . ?
B1 N2 1.514(8) . ?
B1 N1 1.548(6) . ?
C1 N1 1.340(7) . ?
C1 C2 1.396(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.427(7) . ?
C3 H3 0.9300 . ?
C4 N1 1.398(5) . ?
C4 C5 1.419(6) . ?
C5 C6 1.414(6) . ?
C5 C10 1.538(7) . ?
C6 N2 1.394(5) . ?
C6 C7 1.419(7) . ?
C7 C8 1.371(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(9) . ?
C8 H8 0.9300 . ?
C9 N2 1.335(6) . ?
C9 H9 0.9300 . ?
C10 C13 1.497(10) . ?
C10 C11 1.532(10) . ?
C10 C12 1.550(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 F2 108.3(4) . . ?
F1 B1 N2 111.8(5) . . ?
F2 B1 N2 111.5(4) . . ?
F1 B1 N1 110.5(4) . . ?
F2 B1 N1 108.7(5) . . ?
N2 B1 N1 106.1(4) . . ?
N1 C1 C2 109.3(4) . . ?
N1 C1 H1 125.4 . . ?
C2 C1 H1 125.4 . . ?
C3 C2 C1 107.4(5) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
C2 C3 C4 107.9(4) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C5 121.4(4) . . ?
N1 C4 C3 105.8(4) . . ?
C5 C4 C3 132.8(4) . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 C10 120.1(4) . . ?
C4 C5 C10 121.9(4) . . ?
N2 C6 C5 121.3(4) . . ?
N2 C6 C7 106.1(4) . . ?
C5 C6 C7 132.6(4) . . ?
C8 C7 C6 108.3(5) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
C7 C8 C9 106.5(5) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N2 C9 C8 110.9(4) . . ?
N2 C9 H9 124.6 . . ?
C8 C9 H9 124.6 . . ?
C13 C10 C11 106.1(7) . . ?
C13 C10 C5 108.8(4) . . ?
C11 C10 C5 117.7(5) . . ?
C13 C10 C12 108.0(7) . . ?
C11 C10 C12 107.8(6) . . ?
C5 C10 C12 108.1(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 C4 109.6(4) . . ?
C1 N1 B1 124.5(4) . . ?
C4 N1 B1 125.8(4) . . ?
C9 N2 C6 108.1(4) . . ?
C9 N2 B1 124.7(4) . . ?
C6 N2 B1 127.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.064
