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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_060526a
_database_code_depnum_ccdc_archive 'CCDC 1811936'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.	2019-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 B F2 N2 O'
_chemical_formula_weight         338.16

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   23.533(2)
_cell_length_b                   10.2022(11)
_cell_length_c                   16.6772(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.507(6)
_cell_angle_gamma                90.00
_cell_volume                     3449.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5605
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_T_max  0.9812
_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            18897
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3937
_reflns_number_gt                2591
_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)+(0.0692P)²+3.2108P] 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         3937
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_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
F2 F 0.15055(7) 0.20729(16) -0.03574(9) 0.0670(4) Uani 1 1 d . . .
F1 F 0.16222(7) 0.02173(14) 0.04543(10) 0.0654(4) Uani 1 1 d . . .
N2 N 0.08451(8) 0.18080(17) 0.03666(11) 0.0429(4) Uani 1 1 d . . .
N1 N 0.20418(9) 0.22334(19) 0.12994(12) 0.0448(4) Uani 1 1 d . . .
C6 C 0.07874(10) 0.2238(2) 0.11078(14) 0.0421(5) Uani 1 1 d . . .
C4 C 0.19491(11) 0.2719(2) 0.20077(14) 0.0424(5) Uani 1 1 d . . .
C11 C 0.12818(11) 0.3167(2) 0.27388(15) 0.0437(5) Uani 1 1 d . . .
C5 C 0.13410(11) 0.2693(2) 0.19373(14) 0.0410(5) Uani 1 1 d . . .
C9 C 0.02254(11) 0.1533(2) -0.03465(16) 0.0495(6) Uani 1 1 d . . .
C12 C 0.10280(12) 0.4414(2) 0.27190(16) 0.0504(6) Uani 1 1 d . . .
C16 C 0.15145(11) 0.2371(2) 0.35307(15) 0.0469(5) Uani 1 1 d . . .
B1 B 0.15063(13) 0.1550(3) 0.04034(17) 0.0445(6) Uani 1 1 d . . .
C15 C 0.15009(12) 0.2861(2) 0.42946(16) 0.0540(6) Uani 1 1 d . . .
H15 H 0.1652 0.2336 0.4820 0.065 Uiso 1 1 calc R . .
C3 C 0.25597(12) 0.3242(2) 0.27033(16) 0.0534(6) Uani 1 1 d . . .
H3 H 0.2644 0.3630 0.3258 0.064 Uiso 1 1 calc R . .
O1 O -0.04540(10) 0.0961(3) -0.19117(14) 0.0910(7) Uani 1 1 d . . .
C7 C 0.01235(12) 0.2208(2) 0.08470(17) 0.0534(6) Uani 1 1 d . . .
H7 H -0.0052 0.2438 0.1217 0.064 Uiso 1 1 calc R . .
C1 C 0.26668(11) 0.2445(3) 0.15498(17) 0.0571(6) Uani 1 1 d . . .
H1 H 0.2856 0.2208 0.1199 0.068 Uiso 1 1 calc R . .
C13 C 0.10329(13) 0.4853(2) 0.35088(17) 0.0584(7) Uani 1 1 d . . .
H13 H 0.0870 0.5685 0.3503 0.070 Uiso 1 1 calc R . .
C2 C 0.30012(12) 0.3074(3) 0.24135(18) 0.0605(7) Uani 1 1 d . . .
H2 H 0.3442 0.3329 0.2730 0.073 Uiso 1 1 calc R . .
C8 C -0.02242(12) 0.1776(3) -0.00581(18) 0.0588(7) Uani 1 1 d . . .
H8 H -0.0679 0.1665 -0.0414 0.071 Uiso 1 1 calc R . .
C19 C 0.17646(14) 0.1004(3) 0.35620(18) 0.0622(7) Uani 1 1 d . . .
H19A H 0.1897 0.0617 0.4157 0.093 Uiso 1 1 calc R . .
H19B H 0.2135 0.1036 0.3470 0.093 Uiso 1 1 calc R . .
H19C H 0.1421 0.0485 0.3079 0.093 Uiso 1 1 calc R . .
C10 C 0.00946(13) 0.1069(3) -0.12532(17) 0.0643(7) Uani 1 1 d . . .
H10 H 0.0450 0.0848 -0.1324 0.077 Uiso 1 1 calc R . .
C14 C 0.12710(13) 0.4101(3) 0.43036(17) 0.0572(6) Uani 1 1 d . . .
C18 C 0.12790(18) 0.4622(3) 0.5157(2) 0.0793(9) Uani 1 1 d . . .
H18A H 0.1343 0.3911 0.5571 0.119 Uiso 1 1 calc R . .
H18B H 0.0867 0.5047 0.4974 0.119 Uiso 1 1 calc R . .
H18C H 0.1632 0.5242 0.5467 0.119 Uiso 1 1 calc R . .
C17 C 0.07760(16) 0.5304(3) 0.18817(19) 0.0724(8) Uani 1 1 d . . .
H17A H 0.0624 0.6111 0.2004 0.109 Uiso 1 1 calc R . .
H17B H 0.0418 0.4883 0.1350 0.109 Uiso 1 1 calc R . .
H17C H 0.1126 0.5483 0.1760 0.109 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
F2 B1 1.376(3) . ?
F1 B1 1.380(3) . ?
N2 C9 1.363(3) . ?
N2 C6 1.382(3) . ?
N2 B1 1.549(3) . ?
N1 C1 1.327(3) . ?
N1 C4 1.396(3) . ?
N1 B1 1.548(3) . ?
C6 C7 1.393(3) . ?
C6 C5 1.413(3) . ?
C4 C5 1.375(3) . ?
C4 C3 1.415(3) . ?
C11 C12 1.398(3) . ?
C11 C16 1.404(3) . ?
C11 C5 1.493(3) . ?
C9 C8 1.389(3) . ?
C9 C10 1.460(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.512(3) . ?
C16 C15 1.384(3) . ?
C16 C19 1.504(3) . ?
C15 C14 1.379(4) . ?
C15 H15 0.9300 . ?
C3 C2 1.361(4) . ?
C3 H3 0.9300 . ?
O1 C10 1.202(3) . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C1 C2 1.398(4) . ?
C1 H1 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C10 H10 0.9300 . ?
C14 C18 1.510(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C9 N2 C6 107.36(18) . . ?
C9 N2 B1 127.44(18) . . ?
C6 N2 B1 124.87(17) . . ?
C1 N1 C4 107.47(19) . . ?
C1 N1 B1 127.33(19) . . ?
C4 N1 B1 125.19(18) . . ?
N2 C6 C7 108.51(19) . . ?
N2 C6 C5 121.31(19) . . ?
C7 C6 C5 130.0(2) . . ?
C5 C4 N1 121.58(19) . . ?
C5 C4 C3 131.0(2) . . ?
N1 C4 C3 107.32(19) . . ?
C12 C11 C16 120.5(2) . . ?
C12 C11 C5 120.4(2) . . ?
C16 C11 C5 119.1(2) . . ?
C4 C5 C6 119.47(19) . . ?
C4 C5 C11 118.91(19) . . ?
C6 C5 C11 121.61(19) . . ?
N2 C9 C8 109.1(2) . . ?
N2 C9 C10 122.7(2) . . ?
C8 C9 C10 128.3(2) . . ?
C13 C12 C11 118.3(2) . . ?
C13 C12 C17 119.6(2) . . ?
C11 C12 C17 122.1(2) . . ?
C15 C16 C11 118.5(2) . . ?
C15 C16 C19 119.6(2) . . ?
C11 C16 C19 121.9(2) . . ?
F2 B1 F1 110.28(19) . . ?
F2 B1 N1 109.6(2) . . ?
F1 B1 N1 110.24(19) . . ?
F2 B1 N2 111.50(18) . . ?
F1 B1 N2 109.5(2) . . ?
N1 B1 N2 105.71(17) . . ?
C14 C15 C16 122.3(2) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C2 C3 C4 107.6(2) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
C8 C7 C6 107.3(2) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
N1 C1 C2 110.7(2) . . ?
N1 C1 H1 124.7 . . ?
C2 C1 H1 124.7 . . ?
C14 C13 C12 122.4(2) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C3 C2 C1 107.0(2) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C7 C8 C9 107.7(2) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C10 C9 122.7(3) . . ?
O1 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 C18 121.1(2) . . ?
C13 C14 C18 120.9(3) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C9 N2 C6 C7 0.8(2) . . . . ?
B1 N2 C6 C7 -173.0(2) . . . . ?
C9 N2 C6 C5 -175.4(2) . . . . ?
B1 N2 C6 C5 10.8(3) . . . . ?
C1 N1 C4 C5 177.3(2) . . . . ?
B1 N1 C4 C5 -3.9(3) . . . . ?
C1 N1 C4 C3 0.1(3) . . . . ?
B1 N1 C4 C3 178.9(2) . . . . ?
N1 C4 C5 C6 -3.8(3) . . . . ?
C3 C4 C5 C6 172.6(2) . . . . ?
N1 C4 C5 C11 177.03(19) . . . . ?
C3 C4 C5 C11 -6.6(4) . . . . ?
N2 C6 C5 C4 0.5(3) . . . . ?
C7 C6 C5 C4 -174.8(2) . . . . ?
N2 C6 C5 C11 179.63(19) . . . . ?
C7 C6 C5 C11 4.3(4) . . . . ?
C12 C11 C5 C4 101.7(3) . . . . ?
C16 C11 C5 C4 -75.1(3) . . . . ?
C12 C11 C5 C6 -77.4(3) . . . . ?
C16 C11 C5 C6 105.7(2) . . . . ?
C6 N2 C9 C8 -0.5(3) . . . . ?
B1 N2 C9 C8 173.1(2) . . . . ?
C6 N2 C9 C10 179.1(2) . . . . ?
B1 N2 C9 C10 -7.3(4) . . . . ?
C16 C11 C12 C13 2.1(3) . . . . ?
C5 C11 C12 C13 -174.8(2) . . . . ?
C16 C11 C12 C17 179.7(2) . . . . ?
C5 C11 C12 C17 2.8(4) . . . . ?
C12 C11 C16 C15 -1.5(3) . . . . ?
C5 C11 C16 C15 175.4(2) . . . . ?
C12 C11 C16 C19 177.4(2) . . . . ?
C5 C11 C16 C19 -5.7(3) . . . . ?
C1 N1 B1 F2 -48.8(3) . . . . ?
C4 N1 B1 F2 132.7(2) . . . . ?
C1 N1 B1 F1 72.7(3) . . . . ?
C4 N1 B1 F1 -105.8(2) . . . . ?
C1 N1 B1 N2 -169.1(2) . . . . ?
C4 N1 B1 N2 12.4(3) . . . . ?
C9 N2 B1 F2 52.7(3) . . . . ?
C6 N2 B1 F2 -134.8(2) . . . . ?
C9 N2 B1 F1 -69.6(3) . . . . ?
C6 N2 B1 F1 102.9(2) . . . . ?
C9 N2 B1 N1 171.7(2) . . . . ?
C6 N2 B1 N1 -15.8(3) . . . . ?
C11 C16 C15 C14 -0.4(4) . . . . ?
C19 C16 C15 C14 -179.3(2) . . . . ?
C5 C4 C3 C2 -176.6(2) . . . . ?
N1 C4 C3 C2 0.2(3) . . . . ?
N2 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C8 175.0(2) . . . . ?
C4 N1 C1 C2 -0.4(3) . . . . ?
B1 N1 C1 C2 -179.1(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C17 C12 C13 C14 -178.4(3) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
N2 C9 C8 C7 0.1(3) . . . . ?
C10 C9 C8 C7 -179.5(3) . . . . ?
N2 C9 C10 O1 -171.8(3) . . . . ?
C8 C9 C10 O1 7.7(5) . . . . ?
C16 C15 C14 C13 1.6(4) . . . . ?
C16 C15 C14 C18 -178.3(2) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C12 C13 C14 C18 178.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_test_0m
_database_code_depnum_ccdc_archive 'CCDC 1811937'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.	2019-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 B F2 N2 O'
_chemical_formula_weight         296.08

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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.4898(10)
_cell_length_b                   13.5801(13)
_cell_length_c                   20.312(2)
_cell_angle_alpha                101.0320(10)
_cell_angle_beta                 98.3140(10)
_cell_angle_gamma                96.2770(10)
_cell_volume                     2782.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5564
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_T_max  0.9779
_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            32025
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.04
_diffrn_reflns_theta_max         27.58
_reflns_number_total             12508
_reflns_number_gt                6320
_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)+(0.0609P)²+0.8467P] 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         12508
_refine_ls_number_parameters     793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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 1.0666(4) 0.7478(3) 1.00306(18) 0.0540(9) Uani 1 1 d . . .
B2 B 0.5726(3) 0.1545(2) 0.10409(16) 0.0439(8) Uani 1 1 d . . .
B3 B -0.0599(3) 0.8611(2) 0.38871(16) 0.0443(8) Uani 1 1 d . . .
B4 B 0.5364(5) 0.7227(4) 0.5054(2) 0.0854(14) Uani 1 1 d . . .
C1 C 0.9254(3) 0.8784(2) 1.05089(16) 0.0622(8) Uani 1 1 d . . .
H1 H 0.9485 0.8743 1.0961 0.075 Uiso 1 1 calc R . .
C2 C 0.8421(3) 0.9431(2) 1.02798(17) 0.0668(9) Uani 1 1 d . . .
H2 H 0.8003 0.9882 1.0548 0.080 Uiso 1 1 calc R . .
C3 C 0.8335(3) 0.9277(2) 0.95970(17) 0.0574(8) Uani 1 1 d . . .
H3 H 0.7852 0.9609 0.9310 0.069 Uiso 1 1 calc R . .
C4 C 0.9115(3) 0.8519(2) 0.93950(15) 0.0469(7) Uani 1 1 d . . .
C5 C 0.9394(2) 0.80876(19) 0.87678(14) 0.0430(6) Uani 1 1 d . . .
C6 C 1.0245(2) 0.7344(2) 0.87212(14) 0.0434(6) Uani 1 1 d . . .
C7 C 1.0591(3) 0.6763(2) 0.81452(14) 0.0495(7) Uani 1 1 d . . .
H7 H 1.0319 0.6803 0.7696 0.059 Uiso 1 1 calc R . .
C8 C 1.1402(3) 0.6127(2) 0.83634(15) 0.0533(8) Uani 1 1 d . . .
H8 H 1.1784 0.5656 0.8089 0.064 Uiso 1 1 calc R . .
C9 C 1.1554(3) 0.6308(2) 0.90667(15) 0.0489(7) Uani 1 1 d . . .
C10 C 1.2319(3) 0.5803(3) 0.95172(18) 0.0684(9) Uani 1 1 d . . .
H10 H 1.2394 0.6035 0.9985 0.082 Uiso 1 1 calc R . .
C11 C 0.8805(3) 0.83853(19) 0.81459(14) 0.0460(7) Uani 1 1 d . . .
C12 C 0.9574(3) 0.8702(2) 0.77064(16) 0.0624(8) Uani 1 1 d . . .
H12 H 1.0474 0.8750 0.7815 0.075 Uiso 1 1 calc R . .
C13 C 0.9032(4) 0.8947(2) 0.71138(17) 0.0725(10) Uani 1 1 d . . .
H13 H 0.9564 0.9164 0.6826 0.087 Uiso 1 1 calc R . .
C14 C 0.7706(4) 0.8873(2) 0.69460(18) 0.0748(10) Uani 1 1 d . . .
H14 H 0.7337 0.9031 0.6541 0.090 Uiso 1 1 calc R . .
C15 C 0.6930(3) 0.8567(2) 0.73751(18) 0.0682(9) Uani 1 1 d . . .
H15 H 0.6030 0.8519 0.7262 0.082 Uiso 1 1 calc R . .
C16 C 0.7468(3) 0.8330(2) 0.79733(16) 0.0559(8) Uani 1 1 d . . .
H16 H 0.6931 0.8130 0.8264 0.067 Uiso 1 1 calc R . .
C17 C 0.4948(3) 0.1621(2) -0.02052(15) 0.0611(8) Uani 1 1 d . . .
H17 H 0.5233 0.1023 -0.0396 0.073 Uiso 1 1 calc R . .
C18 C 0.4289(3) 0.2234(2) -0.05790(16) 0.0698(9) Uani 1 1 d . . .
H18 H 0.4063 0.2115 -0.1050 0.084 Uiso 1 1 calc R . .
C19 C 0.4041(3) 0.3035(2) -0.01257(15) 0.0573(8) Uani 1 1 d . . .
H19 H 0.3618 0.3568 -0.0228 0.069 Uiso 1 1 calc R . .
C20 C 0.4552(3) 0.29032(19) 0.05355(14) 0.0440(7) Uani 1 1 d . . .
C21 C 0.4637(2) 0.35170(18) 0.11668(13) 0.0411(6) Uani 1 1 d . . .
C22 C 0.5329(2) 0.32529(18) 0.17520(13) 0.0400(6) Uani 1 1 d . . .
C23 C 0.5572(3) 0.3756(2) 0.24350(14) 0.0498(7) Uani 1 1 d . . .
H23 H 0.5313 0.4372 0.2610 0.060 Uiso 1 1 calc R . .
C24 C 0.6262(3) 0.3177(2) 0.28016(15) 0.0550(8) Uani 1 1 d . . .
H24 H 0.6567 0.3332 0.3268 0.066 Uiso 1 1 calc R . .
C25 C 0.6417(3) 0.2318(2) 0.23441(14) 0.0457(7) Uani 1 1 d . . .
C26 C 0.7027(3) 0.1448(2) 0.24885(16) 0.0553(8) Uani 1 1 d . . .
H26 H 0.7084 0.0931 0.2125 0.066 Uiso 1 1 calc R . .
C27 C 0.3949(3) 0.44145(19) 0.12418(13) 0.0416(6) Uani 1 1 d . . .
C28 C 0.2617(3) 0.4285(2) 0.10201(15) 0.0547(8) Uani 1 1 d . . .
H28 H 0.2182 0.3640 0.0817 0.066 Uiso 1 1 calc R . .
C29 C 0.1927(3) 0.5094(2) 0.10956(16) 0.0643(9) Uani 1 1 d . . .
H29 H 0.1031 0.4995 0.0949 0.077 Uiso 1 1 calc R . .
C30 C 0.2566(3) 0.6041(2) 0.13864(15) 0.0612(9) Uani 1 1 d . . .
H30 H 0.2102 0.6588 0.1442 0.073 Uiso 1 1 calc R . .
C31 C 0.3886(3) 0.6192(2) 0.15969(15) 0.0608(8) Uani 1 1 d . . .
H31 H 0.4316 0.6843 0.1786 0.073 Uiso 1 1 calc R . .
C32 C 0.4582(3) 0.5382(2) 0.15298(15) 0.0551(8) Uani 1 1 d . . .
H32 H 0.5477 0.5488 0.1678 0.066 Uiso 1 1 calc R . .
C33 C -0.0020(3) 0.8309(2) 0.50916(14) 0.0596(8) Uani 1 1 d . . .
H33 H -0.0315 0.8885 0.5310 0.072 Uiso 1 1 calc R . .
C34 C 0.0620(3) 0.7641(2) 0.54267(16) 0.0677(9) Uani 1 1 d . . .
H34 H 0.0817 0.7696 0.5895 0.081 Uiso 1 1 calc R . .
C35 C 0.0897(3) 0.6903(2) 0.49399(15) 0.0575(8) Uani 1 1 d . . .
H35 H 0.1331 0.6362 0.5012 0.069 Uiso 1 1 calc R . .
C36 C 0.0399(3) 0.71088(19) 0.42969(14) 0.0443(7) Uani 1 1 d . . .
C37 C 0.0401(2) 0.66061(18) 0.36399(14) 0.0416(6) Uani 1 1 d . . .
C38 C -0.0178(2) 0.69978(19) 0.30850(13) 0.0418(6) Uani 1 1 d . . .
C39 C -0.0404(3) 0.6580(2) 0.23866(14) 0.0516(7) Uani 1 1 d . . .
H39 H -0.0185 0.5964 0.2180 0.062 Uiso 1 1 calc R . .
C40 C -0.1008(3) 0.7243(2) 0.20605(15) 0.0552(8) Uani 1 1 d . . .
H40 H -0.1278 0.7156 0.1594 0.066 Uiso 1 1 calc R . .
C41 C -0.1141(3) 0.8068(2) 0.25566(13) 0.0447(7) Uani 1 1 d . . .
C42 C -0.1656(3) 0.8988(2) 0.24612(15) 0.0518(7) Uani 1 1 d . . .
H42 H -0.1668 0.9485 0.2844 0.062 Uiso 1 1 calc R . .
C43 C 0.1026(3) 0.5683(2) 0.35101(14) 0.0474(7) Uani 1 1 d . . .
C44 C 0.1969(3) 0.5643(2) 0.30955(16) 0.0660(9) Uani 1 1 d . . .
H44 H 0.2162 0.6177 0.2884 0.079 Uiso 1 1 calc R . .
C45 C 0.2616(4) 0.4815(3) 0.29969(19) 0.0841(11) Uani 1 1 d . . .
H45 H 0.3251 0.4796 0.2721 0.101 Uiso 1 1 calc R . .
C46 C 0.2339(4) 0.4021(3) 0.32988(18) 0.0796(11) Uani 1 1 d . . .
H46 H 0.2802 0.3473 0.3242 0.095 Uiso 1 1 calc R . .
C47 C 0.1374(4) 0.4037(2) 0.36856(17) 0.0723(10) Uani 1 1 d . . .
H47 H 0.1157 0.3483 0.3875 0.087 Uiso 1 1 calc R . .
C48 C 0.0720(3) 0.4864(2) 0.37974(15) 0.0602(8) Uani 1 1 d . . .
H48 H 0.0074 0.4870 0.4066 0.072 Uiso 1 1 calc R . .
C49 C 0.3996(4) 0.8580(3) 0.54977(18) 0.0810(11) Uani 1 1 d . . .
H49 H 0.4084 0.8475 0.5940 0.097 Uiso 1 1 calc R . .
C50 C 0.3303(3) 0.9300(3) 0.52572(19) 0.0792(11) Uani 1 1 d . . .
H50 H 0.2857 0.9749 0.5509 0.095 Uiso 1 1 calc R . .
C51 C 0.3399(3) 0.9223(2) 0.45915(18) 0.0668(9) Uani 1 1 d . . .
H51 H 0.3031 0.9609 0.4302 0.080 Uiso 1 1 calc R . .
C52 C 0.4162(3) 0.8446(2) 0.44181(15) 0.0521(7) Uani 1 1 d . . .
C53 C 0.4614(3) 0.8088(2) 0.38266(14) 0.0470(7) Uani 1 1 d . . .
C54 C 0.5446(3) 0.7327(2) 0.38032(14) 0.0456(7) Uani 1 1 d . . .
C55 C 0.6033(3) 0.6863(2) 0.32721(15) 0.0525(7) Uani 1 1 d . . .
H55 H 0.5955 0.6998 0.2837 0.063 Uiso 1 1 calc R . .
C56 C 0.6740(3) 0.6177(2) 0.35079(15) 0.0550(8) Uani 1 1 d . . .
H56 H 0.7237 0.5763 0.3264 0.066 Uiso 1 1 calc R . .
C57 C 0.6580(3) 0.6213(2) 0.41762(15) 0.0553(8) Uani 1 1 d . . .
C58 C 0.7113(4) 0.5584(3) 0.46199(19) 0.0796(11) Uani 1 1 d . . .
H58 H 0.6870 0.5632 0.5046 0.096 Uiso 1 1 calc R . .
C59 C 0.4212(3) 0.84601(19) 0.32017(14) 0.0457(7) Uani 1 1 d . . .
C60 C 0.2901(3) 0.8397(2) 0.29308(17) 0.0570(8) Uani 1 1 d . . .
H60 H 0.2268 0.8170 0.3165 0.068 Uiso 1 1 calc R . .
C61 C 0.2538(3) 0.8669(2) 0.23205(18) 0.0688(10) Uani 1 1 d . . .
H61 H 0.1660 0.8606 0.2137 0.083 Uiso 1 1 calc R . .
C62 C 0.3462(4) 0.9033(2) 0.19798(17) 0.0681(9) Uani 1 1 d . . .
H62 H 0.3211 0.9209 0.1565 0.082 Uiso 1 1 calc R . .
C63 C 0.4749(3) 0.9137(2) 0.22501(16) 0.0632(8) Uani 1 1 d . . .
H63 H 0.5373 0.9401 0.2024 0.076 Uiso 1 1 calc R . .
C64 C 0.5128(3) 0.8853(2) 0.28550(15) 0.0541(8) Uani 1 1 d . . .
H64 H 0.6009 0.8925 0.3035 0.065 Uiso 1 1 calc R . .
F1 F 1.18222(18) 0.79688(16) 1.04189(9) 0.0848(6) Uani 1 1 d . . .
F2 F 1.01645(19) 0.67024(14) 1.03123(9) 0.0791(6) Uani 1 1 d . . .
F3 F 0.69148(16) 0.12826(13) 0.09310(8) 0.0661(5) Uani 1 1 d . . .
F4 F 0.49139(16) 0.06927(11) 0.10859(8) 0.0604(5) Uani 1 1 d . . .
F5 F 0.02855(17) 0.94756(11) 0.39610(8) 0.0636(5) Uani 1 1 d . . .
F6 F -0.18066(16) 0.88825(13) 0.39582(8) 0.0667(5) Uani 1 1 d . . .
F7 F 0.6414(3) 0.7568(3) 0.55354(12) 0.1862(18) Uani 1 1 d . . .
F8 F 0.4651(4) 0.6413(2) 0.51996(17) 0.1750(16) Uani 1 1 d . . .
N1 N 0.9670(2) 0.82377(17) 0.99859(11) 0.0498(6) Uani 1 1 d . . .
N2 N 1.0843(2) 0.70562(16) 0.92892(11) 0.0453(6) Uani 1 1 d . . .
N3 N 0.5111(2) 0.20100(15) 0.04567(11) 0.0457(6) Uani 1 1 d . . .
N4 N 0.58590(19) 0.23643(15) 0.16995(10) 0.0402(5) Uani 1 1 d . . .
N5 N -0.0147(2) 0.80052(16) 0.44226(11) 0.0452(6) Uani 1 1 d . . .
N6 N -0.06416(19) 0.79132(15) 0.31827(10) 0.0386(5) Uani 1 1 d . . .
N7 N 0.4510(2) 0.80701(19) 0.49991(13) 0.0635(7) Uani 1 1 d . . .
N8 N 0.5790(2) 0.69131(17) 0.43565(11) 0.0524(6) Uani 1 1 d . . .
O1 O 1.2860(2) 0.5100(2) 0.93144(13) 0.0933(8) Uani 1 1 d . . .
O2 O 0.7460(2) 0.13686(18) 0.30565(12) 0.0831(7) Uani 1 1 d . . .
O3 O -0.2069(2) 0.91404(17) 0.19074(11) 0.0734(7) Uani 1 1 d . . .
O4 O 0.7857(3) 0.5004(2) 0.44581(14) 0.1003(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 1.372(4) . ?
B1 F2 1.382(4) . ?
B1 N2 1.551(4) . ?
B1 N1 1.552(4) . ?
B2 F3 1.371(3) . ?
B2 F4 1.386(3) . ?
B2 N3 1.542(4) . ?
B2 N4 1.546(3) . ?
B3 F6 1.377(3) . ?
B3 F5 1.384(4) . ?
B3 N5 1.537(4) . ?
B3 N6 1.549(3) . ?
B4 F7 1.337(6) . ?
B4 F8 1.370(6) . ?
B4 N7 1.540(5) . ?
B4 N8 1.543(5) . ?
C1 N1 1.331(3) . ?
C1 C2 1.399(4) . ?
C2 C3 1.351(4) . ?
C3 C4 1.420(4) . ?
C4 C5 1.383(4) . ?
C4 N1 1.396(3) . ?
C5 C6 1.417(3) . ?
C5 C11 1.472(4) . ?
C6 N2 1.377(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.366(4) . ?
C8 C9 1.385(4) . ?
C9 N2 1.370(3) . ?
C9 C10 1.450(4) . ?
C10 O1 1.200(3) . ?
C11 C12 1.383(4) . ?
C11 C16 1.386(4) . ?
C12 C13 1.371(4) . ?
C13 C14 1.371(5) . ?
C14 C15 1.366(5) . ?
C15 C16 1.375(4) . ?
C17 N3 1.326(3) . ?
C17 C18 1.401(4) . ?
C18 C19 1.359(4) . ?
C19 C20 1.424(4) . ?
C20 C21 1.374(3) . ?
C20 N3 1.396(3) . ?
C21 C22 1.428(4) . ?
C21 C27 1.478(3) . ?
C22 N4 1.375(3) . ?
C22 C23 1.397(3) . ?
C23 C24 1.374(4) . ?
C24 C25 1.386(4) . ?
C25 N4 1.371(3) . ?
C25 C26 1.462(4) . ?
C26 O2 1.206(3) . ?
C27 C32 1.383(4) . ?
C27 C28 1.385(4) . ?
C28 C29 1.377(4) . ?
C29 C30 1.363(4) . ?
C30 C31 1.369(4) . ?
C31 C32 1.382(4) . ?
C33 N5 1.325(3) . ?
C33 C34 1.404(4) . ?
C34 C35 1.354(4) . ?
C35 C36 1.425(4) . ?
C36 C37 1.378(3) . ?
C36 N5 1.397(3) . ?
C37 C38 1.422(4) . ?
C37 C43 1.475(3) . ?
C38 N6 1.374(3) . ?
C38 C39 1.398(4) . ?
C39 C40 1.372(4) . ?
C40 C41 1.391(4) . ?
C41 N6 1.368(3) . ?
C41 C42 1.448(4) . ?
C42 O3 1.210(3) . ?
C43 C48 1.381(4) . ?
C43 C44 1.387(4) . ?
C44 C45 1.373(4) . ?
C45 C46 1.364(5) . ?
C46 C47 1.368(5) . ?
C47 C48 1.378(4) . ?
C49 N7 1.329(4) . ?
C49 C50 1.399(5) . ?
C50 C51 1.355(4) . ?
C51 C52 1.414(4) . ?
C52 C53 1.377(4) . ?
C52 N7 1.391(4) . ?
C53 C54 1.422(4) . ?
C53 C59 1.477(4) . ?
C54 N8 1.370(3) . ?
C54 C55 1.398(4) . ?
C55 C56 1.366(4) . ?
C56 C57 1.384(4) . ?
C57 N8 1.361(3) . ?
C57 C58 1.452(4) . ?
C58 O4 1.203(4) . ?
C59 C64 1.390(4) . ?
C59 C60 1.392(4) . ?
C60 C61 1.374(4) . ?
C61 C62 1.373(5) . ?
C62 C63 1.363(4) . ?
C63 C64 1.375(4) . ?

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 110.5(3) . . ?
F1 B1 N2 110.9(3) . . ?
F2 B1 N2 110.2(3) . . ?
F1 B1 N1 109.8(3) . . ?
F2 B1 N1 109.1(3) . . ?
N2 B1 N1 106.2(2) . . ?
F3 B2 F4 109.5(2) . . ?
F3 B2 N3 110.4(2) . . ?
F4 B2 N3 109.8(2) . . ?
F3 B2 N4 111.2(2) . . ?
F4 B2 N4 109.8(2) . . ?
N3 B2 N4 106.2(2) . . ?
F6 B3 F5 109.3(2) . . ?
F6 B3 N5 110.6(2) . . ?
F5 B3 N5 109.7(2) . . ?
F6 B3 N6 110.9(2) . . ?
F5 B3 N6 109.8(2) . . ?
N5 B3 N6 106.5(2) . . ?
F7 B4 F8 110.3(4) . . ?
F7 B4 N7 110.4(4) . . ?
F8 B4 N7 109.5(4) . . ?
F7 B4 N8 109.7(4) . . ?
F8 B4 N8 109.7(4) . . ?
N7 B4 N8 107.2(3) . . ?
N1 C1 C2 110.2(3) . . ?
C3 C2 C1 107.3(3) . . ?
C2 C3 C4 107.8(3) . . ?
C5 C4 N1 120.8(2) . . ?
C5 C4 C3 132.3(3) . . ?
N1 C4 C3 106.9(2) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 C11 120.6(2) . . ?
C6 C5 C11 119.6(2) . . ?
N2 C6 C7 108.5(2) . . ?
N2 C6 C5 121.8(2) . . ?
C7 C6 C5 129.6(3) . . ?
C8 C7 C6 107.5(3) . . ?
C7 C8 C9 107.8(2) . . ?
N2 C9 C8 109.2(2) . . ?
N2 C9 C10 123.6(3) . . ?
C8 C9 C10 127.2(3) . . ?
O1 C10 C9 123.0(3) . . ?
C12 C11 C16 118.1(3) . . ?
C12 C11 C5 120.6(3) . . ?
C16 C11 C5 121.2(3) . . ?
C13 C12 C11 121.1(3) . . ?
C14 C13 C12 120.0(3) . . ?
C15 C14 C13 119.8(3) . . ?
C14 C15 C16 120.5(3) . . ?
C15 C16 C11 120.5(3) . . ?
N3 C17 C18 110.8(3) . . ?
C19 C18 C17 107.3(3) . . ?
C18 C19 C20 107.0(3) . . ?
C21 C20 N3 121.0(2) . . ?
C21 C20 C19 131.1(3) . . ?
N3 C20 C19 107.7(2) . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 C27 119.8(2) . . ?
C22 C21 C27 120.3(2) . . ?
N4 C22 C23 108.6(2) . . ?
N4 C22 C21 120.9(2) . . ?
C23 C22 C21 130.5(2) . . ?
C24 C23 C22 107.8(2) . . ?
C23 C24 C25 106.9(2) . . ?
N4 C25 C24 109.8(2) . . ?
N4 C25 C26 122.2(2) . . ?
C24 C25 C26 128.0(3) . . ?
O2 C26 C25 123.1(3) . . ?
C32 C27 C28 118.5(2) . . ?
C32 C27 C21 122.5(2) . . ?
C28 C27 C21 119.0(2) . . ?
C29 C28 C27 121.2(3) . . ?
C30 C29 C28 119.5(3) . . ?
C29 C30 C31 120.5(3) . . ?
C30 C31 C32 120.3(3) . . ?
C31 C32 C27 120.1(3) . . ?
N5 C33 C34 110.8(3) . . ?
C35 C34 C33 107.1(3) . . ?
C34 C35 C36 107.4(3) . . ?
C37 C36 N5 120.7(2) . . ?
C37 C36 C35 132.0(2) . . ?
N5 C36 C35 107.4(2) . . ?
C36 C37 C38 119.5(2) . . ?
C36 C37 C43 120.4(2) . . ?
C38 C37 C43 120.0(2) . . ?
N6 C38 C39 108.3(2) . . ?
N6 C38 C37 121.8(2) . . ?
C39 C38 C37 129.9(2) . . ?
C40 C39 C38 107.7(2) . . ?
C39 C40 C41 107.4(2) . . ?
N6 C41 C40 109.1(2) . . ?
N6 C41 C42 122.8(2) . . ?
C40 C41 C42 128.0(3) . . ?
O3 C42 C41 123.2(3) . . ?
C48 C43 C44 118.9(3) . . ?
C48 C43 C37 122.1(3) . . ?
C44 C43 C37 119.0(2) . . ?
C45 C44 C43 120.1(3) . . ?
C46 C45 C44 120.8(3) . . ?
C45 C46 C47 119.4(3) . . ?
C46 C47 C48 120.8(3) . . ?
C47 C48 C43 119.9(3) . . ?
N7 C49 C50 109.8(3) . . ?
C51 C50 C49 107.7(3) . . ?
C50 C51 C52 107.3(3) . . ?
C53 C52 N7 120.6(3) . . ?
C53 C52 C51 131.9(3) . . ?
N7 C52 C51 107.4(3) . . ?
C52 C53 C54 120.3(3) . . ?
C52 C53 C59 120.8(2) . . ?
C54 C53 C59 118.9(2) . . ?
N8 C54 C55 108.2(2) . . ?
N8 C54 C53 121.4(2) . . ?
C55 C54 C53 130.4(3) . . ?
C56 C55 C54 107.6(3) . . ?
C55 C56 C57 107.4(3) . . ?
N8 C57 C56 109.3(3) . . ?
N8 C57 C58 124.1(3) . . ?
C56 C57 C58 126.5(3) . . ?
O4 C58 C57 122.6(3) . . ?
C64 C59 C60 118.0(3) . . ?
C64 C59 C53 121.1(2) . . ?
C60 C59 C53 120.8(3) . . ?
C61 C60 C59 120.4(3) . . ?
C62 C61 C60 120.4(3) . . ?
C63 C62 C61 120.0(3) . . ?
C62 C63 C64 120.2(3) . . ?
C63 C64 C59 120.8(3) . . ?
C1 N1 C4 107.7(2) . . ?
C1 N1 B1 126.1(3) . . ?
C4 N1 B1 126.1(2) . . ?
C9 N2 C6 107.0(2) . . ?
C9 N2 B1 127.7(2) . . ?
C6 N2 B1 125.2(2) . . ?
C17 N3 C20 107.2(2) . . ?
C17 N3 B2 127.2(2) . . ?
C20 N3 B2 125.5(2) . . ?
C25 N4 C22 106.9(2) . . ?
C25 N4 B2 127.5(2) . . ?
C22 N4 B2 125.4(2) . . ?
C33 N5 C36 107.3(2) . . ?
C33 N5 B3 126.3(2) . . ?
C36 N5 B3 125.6(2) . . ?
C41 N6 C38 107.6(2) . . ?
C41 N6 B3 127.9(2) . . ?
C38 N6 B3 124.6(2) . . ?
C49 N7 C52 107.9(3) . . ?
C49 N7 B4 126.4(3) . . ?
C52 N7 B4 125.7(3) . . ?
C57 N8 C54 107.5(2) . . ?
C57 N8 B4 127.7(3) . . ?
C54 N8 B4 124.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_test_0m_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1811938'
_audit_update_record             
;
2017-12-18 deposited with the CCDC.	2019-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 B F2 N2 O2'
_chemical_formula_weight         518.35

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5781(10)
_cell_length_b                   24.622(2)
_cell_length_c                   10.7523(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.2950(10)
_cell_angle_gamma                90.00
_cell_volume                     2725.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5491
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9818
_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            23176
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6177
_reflns_number_gt                3796
_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)+(0.0640P)²+0.3695P] 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         6177
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.015
_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 0.6973(2) 0.15634(9) 0.91792(18) 0.0459(5) Uani 1 1 d . . .
C1 C 0.88250(18) 0.09286(8) 0.87601(18) 0.0500(5) Uani 1 1 d . . .
C2 C 0.9040(2) 0.06170(9) 0.7751(2) 0.0644(6) Uani 1 1 d . . .
H2 H 0.9761 0.0400 0.7756 0.077 Uiso 1 1 calc R . .
C3 C 0.7992(2) 0.06885(8) 0.67469(19) 0.0587(5) Uani 1 1 d . . .
H3 H 0.7863 0.0521 0.5952 0.070 Uiso 1 1 calc R . .
C4 C 0.71515(17) 0.10565(7) 0.71285(16) 0.0437(4) Uani 1 1 d . . .
C5 C 0.60631(17) 0.13255(7) 0.64085(15) 0.0411(4) Uani 1 1 d . . .
C6 C 0.55409(17) 0.17640(7) 0.69221(15) 0.0429(4) Uani 1 1 d . . .
C7 C 0.45975(19) 0.21470(9) 0.63573(17) 0.0559(5) Uani 1 1 d . . .
H7 H 0.4099 0.2139 0.5523 0.067 Uiso 1 1 calc R . .
C8 C 0.4547(2) 0.25321(9) 0.72577(18) 0.0617(6) Uani 1 1 d . . .
H8 H 0.4015 0.2837 0.7146 0.074 Uiso 1 1 calc R . .
C9 C 0.54393(18) 0.23839(7) 0.83767(16) 0.0467(4) Uani 1 1 d . . .
C10 C 0.9760(2) 0.09896(9) 1.0031(2) 0.0582(5) Uani 1 1 d . . .
C11 C 0.94240(19) 0.07946(8) 1.12095(18) 0.0515(5) Uani 1 1 d . . .
C12 C 0.8365(2) 0.04576(9) 1.1163(2) 0.0594(5) Uani 1 1 d . . .
H12 H 0.7822 0.0369 1.0379 0.071 Uiso 1 1 calc R . .
C13 C 0.8114(2) 0.02537(11) 1.2274(2) 0.0754(7) Uani 1 1 d . . .
H13 H 0.7410 0.0023 1.2240 0.090 Uiso 1 1 calc R . .
C14 C 0.8899(3) 0.03900(12) 1.3423(2) 0.0854(8) Uani 1 1 d . . .
H14 H 0.8724 0.0252 1.4171 0.103 Uiso 1 1 calc R . .
C15 C 0.9941(3) 0.07270(12) 1.3491(2) 0.0852(8) Uani 1 1 d . . .
H15 H 1.0465 0.0819 1.4281 0.102 Uiso 1 1 calc R . .
C16 C 1.0212(2) 0.09292(9) 1.2387(2) 0.0688(6) Uani 1 1 d . . .
H16 H 1.0924 0.1156 1.2431 0.083 Uiso 1 1 calc R . .
C17 C 0.55011(17) 0.11414(7) 0.50691(15) 0.0423(4) Uani 1 1 d . . .
C18 C 0.60773(18) 0.12918(7) 0.40759(16) 0.0444(4) Uani 1 1 d . . .
C19 C 0.5566(2) 0.10865(8) 0.28636(17) 0.0526(5) Uani 1 1 d . . .
H19 H 0.5948 0.1184 0.2199 0.063 Uiso 1 1 calc R . .
C20 C 0.4515(2) 0.07438(9) 0.26120(18) 0.0586(5) Uani 1 1 d . . .
C21 C 0.3946(2) 0.06115(9) 0.3602(2) 0.0647(6) Uani 1 1 d . . .
H21 H 0.3220 0.0387 0.3438 0.078 Uiso 1 1 calc R . .
C22 C 0.44199(19) 0.08022(8) 0.48395(18) 0.0538(5) Uani 1 1 d . . .
C23 C 0.7207(2) 0.16782(9) 0.4281(2) 0.0654(6) Uani 1 1 d . . .
H23A H 0.7001 0.2000 0.4696 0.098 Uiso 1 1 calc R . .
H23B H 0.7382 0.1773 0.3471 0.098 Uiso 1 1 calc R . .
H23C H 0.7959 0.1508 0.4807 0.098 Uiso 1 1 calc R . .
C24 C 0.3991(3) 0.05148(11) 0.1283(2) 0.0902(8) Uani 1 1 d . . .
H24A H 0.4300 0.0730 0.0670 0.135 Uiso 1 1 calc R . .
H24B H 0.3059 0.0522 0.1087 0.135 Uiso 1 1 calc R . .
H24C H 0.4283 0.0147 0.1251 0.135 Uiso 1 1 calc R . .
C25 C 0.3770(3) 0.06355(12) 0.5890(2) 0.0867(8) Uani 1 1 d . . .
H25A H 0.3309 0.0940 0.6127 0.130 Uiso 1 1 calc R . .
H25B H 0.4417 0.0516 0.6618 0.130 Uiso 1 1 calc R . .
H25C H 0.3172 0.0345 0.5593 0.130 Uiso 1 1 calc R . .
C26 C 0.5749(2) 0.26955(8) 0.96158(18) 0.0515(5) Uani 1 1 d . . .
C27 C 0.5048(2) 0.25514(8) 1.06097(17) 0.0534(5) Uani 1 1 d . . .
C28 C 0.4073(2) 0.21689(9) 1.0393(2) 0.0616(6) Uani 1 1 d . . .
H28 H 0.3877 0.1980 0.9623 0.074 Uiso 1 1 calc R . .
C29 C 0.3385(2) 0.20640(11) 1.1315(2) 0.0776(7) Uani 1 1 d . . .
H29 H 0.2720 0.1809 1.1158 0.093 Uiso 1 1 calc R . .
C30 C 0.3678(3) 0.23334(13) 1.2452(3) 0.0900(9) Uani 1 1 d . . .
H30 H 0.3212 0.2261 1.3069 0.108 Uiso 1 1 calc R . .
C31 C 0.4653(3) 0.27101(13) 1.2690(2) 0.0906(9) Uani 1 1 d . . .
H31 H 0.4855 0.2889 1.3473 0.109 Uiso 1 1 calc R . .
C32 C 0.5341(3) 0.28271(10) 1.1775(2) 0.0741(7) Uani 1 1 d . . .
H32 H 0.5994 0.3088 1.1935 0.089 Uiso 1 1 calc R . .
F1 F 0.78404(12) 0.18777(5) 1.00082(11) 0.0763(4) Uani 1 1 d . . .
F2 F 0.62465(13) 0.12533(5) 0.98148(11) 0.0753(4) Uani 1 1 d . . .
N1 N 0.76804(14) 0.11944(6) 0.83996(13) 0.0423(4) Uani 1 1 d . . .
N2 N 0.60407(14) 0.19230(6) 0.81862(12) 0.0414(4) Uani 1 1 d . . .
O1 O 1.08202(17) 0.11733(9) 1.00267(17) 0.1016(7) Uani 1 1 d . . .
O2 O 0.65125(16) 0.30680(7) 0.97055(16) 0.0782(5) 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 1.364(2) . ?
B1 F2 1.372(3) . ?
B1 N1 1.542(3) . ?
B1 N2 1.553(2) . ?
C1 N1 1.352(2) . ?
C1 C2 1.390(3) . ?
C1 C10 1.499(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.395(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.384(2) . ?
C5 C17 1.496(2) . ?
C6 N2 1.396(2) . ?
C6 C7 1.405(2) . ?
C7 C8 1.365(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(2) . ?
C8 H8 0.9300 . ?
C9 N2 1.340(2) . ?
C9 C26 1.507(3) . ?
C10 O1 1.210(2) . ?
C10 C11 1.473(3) . ?
C11 C12 1.386(3) . ?
C11 C16 1.387(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.392(3) . ?
C17 C18 1.396(2) . ?
C18 C19 1.387(2) . ?
C18 C23 1.503(3) . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(3) . ?
C20 C24 1.518(3) . ?
C21 C22 1.391(3) . ?
C21 H21 0.9300 . ?
C22 C25 1.508(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O2 1.211(2) . ?
C26 C27 1.477(3) . ?
C27 C28 1.376(3) . ?
C27 C32 1.396(3) . ?
C28 C29 1.382(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.363(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.367(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.382(4) . ?
C31 H31 0.9300 . ?
C32 H32 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
F1 B1 F2 111.11(16) . . ?
F1 B1 N1 110.60(16) . . ?
F2 B1 N1 109.90(16) . . ?
F1 B1 N2 110.57(16) . . ?
F2 B1 N2 108.67(16) . . ?
N1 B1 N2 105.84(13) . . ?
N1 C1 C2 109.86(17) . . ?
N1 C1 C10 124.94(17) . . ?
C2 C1 C10 125.10(18) . . ?
C3 C2 C1 107.24(18) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 107.86(17) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C3 107.89(15) . . ?
N1 C4 C5 121.42(15) . . ?
C3 C4 C5 130.09(16) . . ?
C6 C5 C4 120.14(15) . . ?
C6 C5 C17 120.90(15) . . ?
C4 C5 C17 118.94(15) . . ?
C5 C6 N2 120.70(15) . . ?
C5 C6 C7 131.29(16) . . ?
N2 C6 C7 107.75(15) . . ?
C8 C7 C6 107.43(16) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 107.48(17) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
N2 C9 C8 109.90(16) . . ?
N2 C9 C26 123.53(15) . . ?
C8 C9 C26 126.52(17) . . ?
O1 C10 C11 122.16(19) . . ?
O1 C10 C1 116.88(19) . . ?
C11 C10 C1 120.81(18) . . ?
C12 C11 C16 119.2(2) . . ?
C12 C11 C10 121.15(18) . . ?
C16 C11 C10 119.6(2) . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 120.60(16) . . ?
C22 C17 C5 118.75(16) . . ?
C18 C17 C5 120.62(16) . . ?
C19 C18 C17 118.55(17) . . ?
C19 C18 C23 119.58(17) . . ?
C17 C18 C23 121.85(16) . . ?
C20 C19 C18 122.19(18) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C21 118.13(17) . . ?
C19 C20 C24 121.2(2) . . ?
C21 C20 C24 120.7(2) . . ?
C20 C21 C22 122.28(19) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C21 C22 C17 118.23(18) . . ?
C21 C22 C25 119.91(19) . . ?
C17 C22 C25 121.86(18) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 C26 C27 124.12(18) . . ?
O2 C26 C9 117.47(19) . . ?
C27 C26 C9 118.30(19) . . ?
C28 C27 C32 119.2(2) . . ?
C28 C27 C26 121.54(18) . . ?
C32 C27 C26 119.2(2) . . ?
C27 C28 C29 120.3(2) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.3(3) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 120.4(2) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 119.6(3) . . ?
C31 C32 H32 120.2 . . ?
C27 C32 H32 120.2 . . ?
C1 N1 C4 107.11(15) . . ?
C1 N1 B1 130.09(15) . . ?
C4 N1 B1 122.73(14) . . ?
C9 N2 C6 107.43(14) . . ?
C9 N2 B1 128.79(14) . . ?
C6 N2 B1 123.22(14) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1815587'
_audit_update_record             
;
2018-01-09 deposited with the CCDC.	2019-05-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        2017
_chemical_formula_moiety         '0.06(C27 H22 B2 F4 N4)'
_chemical_formula_sum            'C1.69 H1.38 B0.12 F0.25 N0.25'
_chemical_formula_weight         31.26
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.522(3)
_cell_length_b                   15.930(4)
_cell_length_c                   13.262(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.631(3)
_cell_angle_gamma                90
_cell_volume                     2404.7(11)
_cell_formula_units_Z            64
_cell_measurement_reflns_used    3734
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1107 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.8826.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull reddish red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1032
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1258
_diffrn_reflns_av_unetI/netI     0.1235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22141
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.304
_diffrn_reflns_theta_min         1.789
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2131
_reflns_number_total             4358
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1884
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      0.887
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2292
_refine_ls_wR_factor_ref         0.2878
_refine_special_details          ?
_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.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C21(H21), C14(H14), C23(H23), C12(H12), C3(H3), C13(H13),
 C24(H24), C7(H7), C25(H25), C22(H22), C26(H26)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F4 F 0.1113(3) 0.24308(17) 0.0910(2) 0.0633(9) Uani 1 1 d . . . . .
F3 F -0.0350(2) 0.31744(19) 0.1065(3) 0.0674(9) Uani 1 1 d . . . . .
F2 F 0.0470(3) 0.6218(3) 0.3043(3) 0.0973(13) Uani 1 1 d . . . . .
N2 N 0.2490(3) 0.5800(2) 0.3932(3) 0.0421(10) Uani 1 1 d . . . . .
N1 N 0.1434(3) 0.6314(2) 0.5035(3) 0.0446(10) Uani 1 1 d . . . . .
N3 N 0.1565(3) 0.3226(2) 0.2568(3) 0.0448(10) Uani 1 1 d . . . . .
N4 N 0.1180(3) 0.3931(2) 0.0815(3) 0.0456(10) Uani 1 1 d . . . . .
F1 F 0.0860(3) 0.5038(2) 0.4041(4) 0.1109(15) Uani 1 1 d . . . . .
C5 C 0.4233(4) 0.7555(3) 0.5857(4) 0.0404(12) Uani 1 1 d . . . . .
C15 C 0.3325(4) 0.6427(3) 0.4428(4) 0.0401(11) Uani 1 1 d . . . . .
C18 C 0.2789(4) 0.5405(3) 0.3171(4) 0.0429(12) Uani 1 1 d . . . . .
C27 C 0.1731(4) 0.4651(3) 0.1396(4) 0.0433(12) Uani 1 1 d . . . . .
C6 C 0.4228(4) 0.8351(3) 0.5415(4) 0.0451(12) Uani 1 1 d . . . . .
C10 C 0.3264(4) 0.6950(3) 0.5267(4) 0.0417(12) Uani 1 1 d . . . . .
C11 C 0.2349(4) 0.6879(3) 0.5574(4) 0.0407(11) Uani 1 1 d . . . . .
C19 C 0.2180(4) 0.4655(3) 0.2555(4) 0.0407(12) Uani 1 1 d . . . . .
C4 C 0.5140(4) 0.7337(3) 0.6876(4) 0.0438(12) Uani 1 1 d . . . . .
C20 C 0.2132(4) 0.3939(3) 0.3128(4) 0.0412(12) Uani 1 1 d . . . . .
C17 C 0.3796(4) 0.5772(3) 0.3187(4) 0.0500(13) Uani 1 1 d . . . . .
H17 H 0.4177 0.5622 0.2743 0.060 Uiso 1 1 calc R . . . .
C16 C 0.4139(4) 0.6402(3) 0.3977(4) 0.0455(12) Uani 1 1 d . . . . .
H16 H 0.4796 0.6745 0.4169 0.055 Uiso 1 1 calc R . . . .
C2 C 0.6028(4) 0.8707(3) 0.7011(4) 0.0533(14) Uani 1 1 d . . . . .
C21 C 0.2696(5) 0.3734(3) 0.4258(4) 0.0562(14) Uani 1 1 d . . . . .
H21 H 0.3152 0.4091 0.4830 0.067 Uiso 1 1 calc R . . . .
C14 C 0.0733(4) 0.6336(3) 0.5553(4) 0.0527(13) Uani 1 1 d . . . . .
H14 H 0.0059 0.6012 0.5362 0.063 Uiso 1 1 calc R . . . .
C23 C 0.1749(5) 0.2615(3) 0.3306(4) 0.0562(14) Uani 1 1 d . . . . .
H23 H 0.1452 0.2073 0.3140 0.067 Uiso 1 1 calc R . . . .
C12 C 0.2138(5) 0.7258(3) 0.6438(4) 0.0512(13) Uani 1 1 d . . . . .
H12 H 0.2598 0.7669 0.6924 0.061 Uiso 1 1 calc R . . . .
C3 C 0.6011(4) 0.7912(3) 0.7418(4) 0.0503(13) Uani 1 1 d . . . . .
H3 H 0.6616 0.7758 0.8089 0.060 Uiso 1 1 calc R . . . .
C13 C 0.1146(5) 0.6917(4) 0.6432(4) 0.0604(15) Uani 1 1 d . . . . .
H13 H 0.0803 0.7043 0.6915 0.072 Uiso 1 1 calc R . . . .
C24 C 0.0851(4) 0.4092(3) -0.0270(4) 0.0536(13) Uani 1 1 d . . . . .
H24 H 0.0447 0.3719 -0.0842 0.064 Uiso 1 1 calc R . . . .
C7 C 0.5120(5) 0.8910(3) 0.5998(4) 0.0557(14) Uani 1 1 d . . . . .
H7 H 0.5110 0.9441 0.5702 0.067 Uiso 1 1 calc R . . . .
C25 C 0.1198(5) 0.4884(4) -0.0412(4) 0.0610(15) Uani 1 1 d . . . . .
H25 H 0.1086 0.5130 -0.1084 0.073 Uiso 1 1 calc R . . . .
C22 C 0.2453(5) 0.2910(4) 0.4362(4) 0.0663(16) Uani 1 1 d . . . . .
H22 H 0.2710 0.2604 0.5018 0.080 Uiso 1 1 calc R . . . .
C8 C 0.5183(5) 0.6474(3) 0.7380(5) 0.0660(16) Uani 1 1 d . . . . .
H8A H 0.4555 0.6423 0.7612 0.099 Uiso 1 1 calc GR . . . .
H8B H 0.5922 0.6402 0.8008 0.099 Uiso 1 1 calc GR . . . .
H8C H 0.5098 0.6050 0.6836 0.099 Uiso 1 1 calc GR . . . .
C26 C 0.1745(4) 0.5249(3) 0.0629(4) 0.0547(14) Uani 1 1 d . . . . .
H26 H 0.2060 0.5787 0.0786 0.066 Uiso 1 1 calc R . . . .
C9 C 0.3273(5) 0.8597(3) 0.4308(4) 0.0656(16) Uani 1 1 d . . . . .
H9A H 0.3427 0.8346 0.3723 0.098 Uiso 1 1 calc GR . . . .
H9B H 0.3257 0.9197 0.4233 0.098 Uiso 1 1 calc GR . . . .
H9C H 0.2528 0.8404 0.4262 0.098 Uiso 1 1 calc GR . . . .
B2 B 0.0832(5) 0.3158(4) 0.1301(5) 0.0455(14) Uani 1 1 d . . . . .
C1 C 0.7000(5) 0.9314(4) 0.7633(5) 0.0836(19) Uani 1 1 d . . . . .
H1A H 0.6685 0.9784 0.7873 0.125 Uiso 1 1 calc GR . . . .
H1B H 0.7352 0.9508 0.7156 0.125 Uiso 1 1 calc GR . . . .
H1C H 0.7584 0.9039 0.8267 0.125 Uiso 1 1 calc GR . . . .
B1 B 0.1252(6) 0.5809(4) 0.3967(5) 0.0570(16) 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
F4 B2 1.373(6) . ?
F3 B2 1.380(6) . ?
F2 B1 1.373(7) . ?
N2 C15 1.396(6) . ?
N2 C18 1.367(6) . ?
N2 B1 1.571(7) . ?
N1 C11 1.397(6) . ?
N1 C14 1.321(6) . ?
N1 B1 1.561(7) . ?
N3 C20 1.381(6) . ?
N3 C23 1.329(6) . ?
N3 B2 1.547(7) . ?
N4 C27 1.394(5) . ?
N4 C24 1.346(6) . ?
N4 B2 1.534(7) . ?
F1 B1 1.342(7) . ?
C5 C6 1.396(6) . ?
C5 C10 1.491(6) . ?
C5 C4 1.399(6) . ?
C15 C10 1.417(6) . ?
C15 C16 1.382(6) . ?
C18 C19 1.469(6) . ?
C18 C17 1.383(6) . ?
C27 C19 1.399(6) . ?
C27 C26 1.400(6) . ?
C6 C7 1.386(7) . ?
C6 C9 1.509(7) . ?
C10 C11 1.371(6) . ?
C11 C12 1.415(6) . ?
C19 C20 1.384(6) . ?
C4 C3 1.375(7) . ?
C4 C8 1.519(7) . ?
C20 C21 1.404(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.383(6) . ?
C16 H16 0.9300 . ?
C2 C3 1.381(7) . ?
C2 C7 1.388(7) . ?
C2 C1 1.504(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.367(7) . ?
C14 H14 0.9300 . ?
C14 C13 1.408(7) . ?
C23 H23 0.9300 . ?
C23 C22 1.389(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.352(7) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.372(7) . ?
C7 H7 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.388(7) . ?
C22 H22 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C26 H26 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C15 N2 B1 122.3(4) . . ?
C18 N2 C15 107.2(4) . . ?
C18 N2 B1 127.1(4) . . ?
C11 N1 B1 125.1(4) . . ?
C14 N1 C11 107.4(4) . . ?
C14 N1 B1 127.4(4) . . ?
C20 N3 B2 125.5(4) . . ?
C23 N3 C20 108.3(4) . . ?
C23 N3 B2 126.2(4) . . ?
C27 N4 B2 126.2(4) . . ?
C24 N4 C27 107.1(4) . . ?
C24 N4 B2 126.0(4) . . ?
C6 C5 C10 120.4(4) . . ?
C6 C5 C4 119.4(4) . . ?
C4 C5 C10 120.1(4) . . ?
N2 C15 C10 121.1(4) . . ?
C16 C15 N2 108.5(4) . . ?
C16 C15 C10 130.4(4) . . ?
N2 C18 C19 123.2(4) . . ?
N2 C18 C17 108.8(4) . . ?
C17 C18 C19 127.7(4) . . ?
N4 C27 C19 119.4(4) . . ?
N4 C27 C26 108.2(4) . . ?
C19 C27 C26 132.4(4) . . ?
C5 C6 C9 120.5(4) . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 C9 120.3(4) . . ?
C15 C10 C5 119.6(4) . . ?
C11 C10 C5 119.7(4) . . ?
C11 C10 C15 120.7(4) . . ?
N1 C11 C12 107.4(4) . . ?
C10 C11 N1 120.6(4) . . ?
C10 C11 C12 131.9(4) . . ?
C27 C19 C18 119.5(4) . . ?
C20 C19 C18 119.7(4) . . ?
C20 C19 C27 120.6(4) . . ?
C5 C4 C8 121.0(4) . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 C8 119.9(4) . . ?
N3 C20 C19 120.9(4) . . ?
N3 C20 C21 107.4(4) . . ?
C19 C20 C21 131.3(4) . . ?
C18 C17 H17 125.9 . . ?
C16 C17 C18 108.2(4) . . ?
C16 C17 H17 125.9 . . ?
C15 C16 C17 107.2(4) . . ?
C15 C16 H16 126.4 . . ?
C17 C16 H16 126.4 . . ?
C3 C2 C7 116.9(4) . . ?
C3 C2 C1 121.1(5) . . ?
C7 C2 C1 122.0(5) . . ?
C20 C21 H21 126.3 . . ?
C22 C21 C20 107.3(5) . . ?
C22 C21 H21 126.3 . . ?
N1 C14 H14 124.7 . . ?
N1 C14 C13 110.7(4) . . ?
C13 C14 H14 124.7 . . ?
N3 C23 H23 125.1 . . ?
N3 C23 C22 109.7(5) . . ?
C22 C23 H23 125.1 . . ?
C11 C12 H12 126.1 . . ?
C13 C12 C11 107.8(4) . . ?
C13 C12 H12 126.1 . . ?
C4 C3 C2 123.0(5) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C14 C13 H13 126.6 . . ?
C12 C13 C14 106.8(4) . . ?
C12 C13 H13 126.6 . . ?
N4 C24 H24 124.8 . . ?
N4 C24 C25 110.4(5) . . ?
C25 C24 H24 124.8 . . ?
C6 C7 C2 122.3(5) . . ?
C6 C7 H7 118.8 . . ?
C2 C7 H7 118.8 . . ?
C24 C25 H25 126.2 . . ?
C24 C25 C26 107.6(5) . . ?
C26 C25 H25 126.2 . . ?
C21 C22 C23 107.3(5) . . ?
C21 C22 H22 126.4 . . ?
C23 C22 H22 126.4 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C27 C26 H26 126.7 . . ?
C25 C26 C27 106.7(4) . . ?
C25 C26 H26 126.7 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F4 B2 F3 110.5(4) . . ?
F4 B2 N3 109.9(4) . . ?
F4 B2 N4 110.9(4) . . ?
F3 B2 N3 109.8(4) . . ?
F3 B2 N4 110.8(4) . . ?
N4 B2 N3 104.9(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
F2 B1 N2 108.9(4) . . ?
F2 B1 N1 110.2(5) . . ?
N1 B1 N2 105.0(4) . . ?
F1 B1 F2 110.7(5) . . ?
F1 B1 N2 112.9(5) . . ?
F1 B1 N1 109.0(5) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
