# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc1q9t83
_database_code_depnum_ccdc_archive 'CCDC 1588355'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H37 B F2 N2'
_chemical_formula_weight         642.57

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           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                   26.687(2)
_cell_length_b                   11.1023(9)
_cell_length_c                   23.908(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6550(10)
_cell_angle_gamma                90.00
_cell_volume                     6983.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8424
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2704
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_T_max  0.9846
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34473
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.35
_reflns_number_total             6404
_reflns_number_gt                4183
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0513P)²+2.7230P] 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         6404
_refine_ls_number_parameters     445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1237
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_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 0.64942(8) 0.6530(2) 0.27247(9) 0.0443(5) Uani 1 1 d . . .
C1 C 0.63749(7) 0.56756(18) 0.16967(8) 0.0490(5) Uani 1 1 d . . .
C2 C 0.66805(7) 0.5415(2) 0.12916(8) 0.0585(6) Uani 1 1 d . . .
H2 H 0.6572 0.5083 0.0935 0.070 Uiso 1 1 calc R . .
C3 C 0.71663(8) 0.57319(18) 0.15126(8) 0.0538(5) Uani 1 1 d . . .
H3 H 0.7448 0.5659 0.1333 0.065 Uiso 1 1 calc R . .
C4 C 0.71645(7) 0.61869(17) 0.20573(8) 0.0455(5) Uani 1 1 d . . .
C5 C 0.75584(7) 0.66427(16) 0.24556(8) 0.0441(4) Uani 1 1 d . . .
C6 C 0.74662(7) 0.70314(17) 0.29812(7) 0.0439(4) Uani 1 1 d . . .
C7 C 0.77901(7) 0.75386(18) 0.34415(8) 0.0531(5) Uani 1 1 d . . .
H7 H 0.8133 0.7710 0.3459 0.064 Uiso 1 1 calc R . .
C8 C 0.75092(7) 0.77366(19) 0.38625(8) 0.0551(5) Uani 1 1 d . . .
H8 H 0.7627 0.8075 0.4216 0.066 Uiso 1 1 calc R . .
C9 C 0.70126(7) 0.73397(17) 0.36662(7) 0.0467(5) Uani 1 1 d . . .
C10 C 0.58077(7) 0.55221(19) 0.16458(8) 0.0543(5) Uani 1 1 d . . .
H10 H 0.5737 0.5368 0.2029 0.065 Uiso 1 1 calc R . .
C11 C 0.56495(7) 0.4400(2) 0.12948(8) 0.0515(5) Uani 1 1 d . . .
C12 C 0.57425(8) 0.3280(2) 0.15457(9) 0.0643(6) Uani 1 1 d . . .
H12 H 0.5880 0.3233 0.1929 0.077 Uiso 1 1 calc R . .
C13 C 0.56359(9) 0.2235(2) 0.12397(11) 0.0714(7) Uani 1 1 d . . .
H13 H 0.5698 0.1492 0.1417 0.086 Uiso 1 1 calc R . .
C14 C 0.54385(9) 0.2287(2) 0.06750(11) 0.0707(6) Uani 1 1 d . . .
H14 H 0.5366 0.1582 0.0467 0.085 Uiso 1 1 calc R . .
C15 C 0.53490(10) 0.3377(2) 0.04185(10) 0.0792(7) Uani 1 1 d . . .
H15 H 0.5217 0.3413 0.0033 0.095 Uiso 1 1 calc R . .
C16 C 0.54511(9) 0.4427(2) 0.07227(9) 0.0723(7) Uani 1 1 d . . .
H16 H 0.5386 0.5165 0.0541 0.087 Uiso 1 1 calc R . .
C17 C 0.55242(7) 0.6667(2) 0.14344(9) 0.0580(6) Uani 1 1 d . . .
C18 C 0.56719(9) 0.7395(2) 0.10268(11) 0.0739(7) Uani 1 1 d . . .
H18 H 0.5957 0.7189 0.0872 0.089 Uiso 1 1 calc R . .
C19 C 0.54044(11) 0.8434(2) 0.08415(13) 0.0929(8) Uani 1 1 d . . .
H19 H 0.5510 0.8909 0.0563 0.111 Uiso 1 1 calc R . .
C20 C 0.49891(12) 0.8757(3) 0.10659(17) 0.1053(10) Uani 1 1 d . . .
H20 H 0.4809 0.9450 0.0940 0.126 Uiso 1 1 calc R . .
C21 C 0.48375(10) 0.8061(3) 0.14767(16) 0.1036(10) Uani 1 1 d . . .
H21 H 0.4556 0.8288 0.1635 0.124 Uiso 1 1 calc R . .
C22 C 0.51008(9) 0.7013(3) 0.16604(11) 0.0840(8) Uani 1 1 d . . .
H22 H 0.4992 0.6540 0.1938 0.101 Uiso 1 1 calc R . .
C23 C 0.80820(7) 0.67047(17) 0.23067(7) 0.0454(5) Uani 1 1 d . . .
C24 C 0.81961(7) 0.76191(19) 0.19474(8) 0.0529(5) Uani 1 1 d . . .
C25 C 0.86766(8) 0.7630(2) 0.17958(9) 0.0641(6) Uani 1 1 d . . .
H25 H 0.8757 0.8245 0.1562 0.077 Uiso 1 1 calc R . .
C26 C 0.90365(8) 0.6775(2) 0.19763(9) 0.0650(6) Uani 1 1 d . . .
C27 C 0.89164(8) 0.5887(2) 0.23342(9) 0.0630(6) Uani 1 1 d . . .
H27 H 0.9159 0.5304 0.2463 0.076 Uiso 1 1 calc R . .
C28 C 0.84457(7) 0.58321(18) 0.25103(8) 0.0514(5) Uani 1 1 d . . .
C29 C 0.78190(9) 0.8581(2) 0.17267(11) 0.0794(7) Uani 1 1 d . . .
H29A H 0.7968 0.9122 0.1488 0.119 Uiso 1 1 calc R . .
H29B H 0.7726 0.9020 0.2040 0.119 Uiso 1 1 calc R . .
H29C H 0.7522 0.8216 0.1511 0.119 Uiso 1 1 calc R . .
C30 C 0.95482(9) 0.6803(3) 0.17827(12) 0.1053(10) Uani 1 1 d . . .
H30A H 0.9501 0.6697 0.1379 0.158 Uiso 1 1 calc R . .
H30B H 0.9758 0.6165 0.1965 0.158 Uiso 1 1 calc R . .
H30C H 0.9710 0.7564 0.1882 0.158 Uiso 1 1 calc R . .
C31 C 0.83362(9) 0.4833(2) 0.28923(10) 0.0748(7) Uani 1 1 d . . .
H31A H 0.8089 0.4298 0.2686 0.112 Uiso 1 1 calc R . .
H31B H 0.8206 0.5163 0.3210 0.112 Uiso 1 1 calc R . .
H31C H 0.8644 0.4396 0.3026 0.112 Uiso 1 1 calc R . .
C32 C 0.65715(7) 0.72737(18) 0.39820(8) 0.0494(5) Uani 1 1 d . . .
H32 H 0.6262 0.7305 0.3696 0.059 Uiso 1 1 calc R . .
C33 C 0.65637(9) 0.60769(19) 0.42844(8) 0.0557(5) Uani 1 1 d . . .
C34 C 0.70009(10) 0.5570(2) 0.45815(9) 0.0713(7) Uani 1 1 d . . .
H34 H 0.7309 0.5974 0.4600 0.086 Uiso 1 1 calc R . .
C35 C 0.69892(15) 0.4476(3) 0.48511(12) 0.0996(10) Uani 1 1 d . . .
H35 H 0.7287 0.4144 0.5049 0.120 Uiso 1 1 calc R . .
C36 C 0.6535(2) 0.3879(3) 0.48262(14) 0.1123(13) Uani 1 1 d . . .
H36 H 0.6525 0.3139 0.5006 0.135 Uiso 1 1 calc R . .
C37 C 0.61012(17) 0.4370(3) 0.45385(14) 0.1083(11) Uani 1 1 d . . .
H37 H 0.5794 0.3967 0.4525 0.130 Uiso 1 1 calc R . .
C38 C 0.61126(10) 0.5462(2) 0.42664(10) 0.0792(7) Uani 1 1 d . . .
H38 H 0.5813 0.5786 0.4069 0.095 Uiso 1 1 calc R . .
C39 C 0.65572(7) 0.83686(18) 0.43633(8) 0.0497(5) Uani 1 1 d . . .
C40 C 0.65297(8) 0.8274(2) 0.49331(8) 0.0610(6) Uani 1 1 d . . .
H40 H 0.6524 0.7516 0.5097 0.073 Uiso 1 1 calc R . .
C41 C 0.65110(10) 0.9286(2) 0.52614(10) 0.0781(7) Uani 1 1 d . . .
H41 H 0.6494 0.9206 0.5645 0.094 Uiso 1 1 calc R . .
C42 C 0.65166(11) 1.0400(2) 0.50285(11) 0.0884(8) Uani 1 1 d . . .
H42 H 0.6509 1.1082 0.5253 0.106 Uiso 1 1 calc R . .
C43 C 0.65334(11) 1.0514(2) 0.44581(11) 0.0882(8) Uani 1 1 d . . .
H43 H 0.6530 1.1274 0.4294 0.106 Uiso 1 1 calc R . .
C44 C 0.65545(9) 0.9506(2) 0.41331(10) 0.0707(6) Uani 1 1 d . . .
H44 H 0.6567 0.9591 0.3749 0.085 Uiso 1 1 calc R . .
F1 F 0.61575(4) 0.74757(11) 0.26321(5) 0.0646(3) Uani 1 1 d . . .
F2 F 0.62648(4) 0.55790(11) 0.29515(4) 0.0620(3) Uani 1 1 d . . .
N1 N 0.66663(5) 0.61431(14) 0.21624(6) 0.0444(4) Uani 1 1 d . . .
N2 N 0.69824(5) 0.69295(13) 0.31302(6) 0.0427(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.376(2) . ?
B1 F2 1.376(2) . ?
B1 N1 1.552(2) . ?
B1 N2 1.552(3) . ?
C1 N1 1.350(2) . ?
C1 C2 1.397(3) . ?
C1 C10 1.508(3) . ?
C2 C3 1.362(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 N1 1.395(2) . ?
C5 C6 1.389(2) . ?
C5 C23 1.500(2) . ?
C6 C7 1.399(3) . ?
C6 N2 1.400(2) . ?
C7 C8 1.370(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.350(2) . ?
C9 C32 1.503(3) . ?
C10 C11 1.522(3) . ?
C10 C17 1.521(3) . ?
C10 H10 0.9800 . ?
C11 C16 1.382(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C17 C22 1.386(3) . ?
C18 C19 1.389(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.358(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.396(3) . ?
C23 C28 1.400(3) . ?
C24 C25 1.390(3) . ?
C24 C29 1.501(3) . ?
C25 C26 1.368(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(3) . ?
C26 C30 1.514(3) . ?
C27 C28 1.391(3) . ?
C27 H27 0.9300 . ?
C28 C31 1.497(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.514(3) . ?
C32 C39 1.524(3) . ?
C32 H32 0.9800 . ?
C33 C38 1.379(3) . ?
C33 C34 1.380(3) . ?
C34 C35 1.378(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.374(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.358(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.378(4) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C44 1.377(3) . ?
C39 C40 1.380(3) . ?
C40 C41 1.376(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.358(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.378(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.369(3) . ?
C43 H43 0.9300 . ?
C44 H44 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 109.10(15) . . ?
F1 B1 N1 110.60(15) . . ?
F2 B1 N1 110.17(16) . . ?
F1 B1 N2 109.84(16) . . ?
F2 B1 N2 110.81(15) . . ?
N1 B1 N2 106.29(14) . . ?
N1 C1 C2 109.20(16) . . ?
N1 C1 C10 122.79(16) . . ?
C2 C1 C10 127.99(17) . . ?
C3 C2 C1 107.81(17) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
C2 C3 C4 107.65(17) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
C5 C4 N1 121.58(16) . . ?
C5 C4 C3 130.50(17) . . ?
N1 C4 C3 107.91(16) . . ?
C6 C5 C4 120.29(16) . . ?
C6 C5 C23 120.92(16) . . ?
C4 C5 C23 118.79(16) . . ?
C5 C6 C7 131.06(17) . . ?
C5 C6 N2 121.05(16) . . ?
C7 C6 N2 107.88(15) . . ?
C8 C7 C6 107.49(17) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 107.87(17) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C8 109.07(16) . . ?
N2 C9 C32 122.23(16) . . ?
C8 C9 C32 128.59(17) . . ?
C1 C10 C11 108.60(16) . . ?
C1 C10 C17 111.66(17) . . ?
C11 C10 C17 115.10(16) . . ?
C1 C10 H10 107.0 . . ?
C11 C10 H10 107.0 . . ?
C17 C10 H10 107.0 . . ?
C16 C11 C12 117.4(2) . . ?
C16 C11 C10 123.55(19) . . ?
C12 C11 C10 118.90(18) . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C18 C17 C22 117.5(2) . . ?
C18 C17 C10 122.79(19) . . ?
C22 C17 C10 119.7(2) . . ?
C17 C18 C19 121.5(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.7(3) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C28 120.47(17) . . ?
C24 C23 C5 119.17(17) . . ?
C28 C23 C5 120.33(17) . . ?
C25 C24 C23 118.2(2) . . ?
C25 C24 C29 119.7(2) . . ?
C23 C24 C29 122.07(18) . . ?
C26 C25 C24 122.8(2) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C25 C26 C27 117.91(19) . . ?
C25 C26 C30 120.8(2) . . ?
C27 C26 C30 121.3(2) . . ?
C26 C27 C28 122.4(2) . . ?
C26 C27 H27 118.8 . . ?
C28 C27 H27 118.8 . . ?
C27 C28 C23 118.22(19) . . ?
C27 C28 C31 119.7(2) . . ?
C23 C28 C31 122.02(18) . . ?
C24 C29 H29A 109.5 . . ?
C24 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C24 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C9 C32 C33 110.92(16) . . ?
C9 C32 C39 111.22(15) . . ?
C33 C32 C39 114.24(15) . . ?
C9 C32 H32 106.7 . . ?
C33 C32 H32 106.7 . . ?
C39 C32 H32 106.7 . . ?
C38 C33 C34 118.2(2) . . ?
C38 C33 C32 120.1(2) . . ?
C34 C33 C32 121.7(2) . . ?
C35 C34 C33 121.1(3) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C36 C35 C34 119.6(3) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C37 C36 C35 119.9(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.5(3) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C33 120.6(3) . . ?
C37 C38 H38 119.7 . . ?
C33 C38 H38 119.7 . . ?
C44 C39 C40 117.81(19) . . ?
C44 C39 C32 119.43(17) . . ?
C40 C39 C32 122.72(18) . . ?
C41 C40 C39 120.9(2) . . ?
C41 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
C42 C41 C40 120.4(2) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C41 C42 C43 119.6(2) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C44 C43 C42 119.9(2) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C39 121.4(2) . . ?
C43 C44 H44 119.3 . . ?
C39 C44 H44 119.3 . . ?
C1 N1 C4 107.43(14) . . ?
C1 N1 B1 127.39(15) . . ?
C4 N1 B1 125.15(15) . . ?
C9 N2 C6 107.66(15) . . ?
C9 N2 B1 126.84(15) . . ?
C6 N2 B1 125.26(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_150313b_0m
_database_code_depnum_ccdc_archive 'CCDC 1588396'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 B F2 N2'
_chemical_formula_weight         338.20

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.5066(11)
_cell_length_b                   11.9871(12)
_cell_length_c                   13.3556(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.8100(10)
_cell_angle_gamma                90.00
_cell_volume                     1796.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6570
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_T_max  0.9887
_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            15237
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_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         1.81
_diffrn_reflns_theta_max         27.65
_reflns_number_total             4163
_reflns_number_gt                2997
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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)+(0.0902P)²+0.2749P] 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         4163
_refine_ls_number_parameters     229
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.097
_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 0.85026(16) 0.14395(15) 0.06513(14) 0.0535(4) Uani 1 1 d . . .
C1 C 0.99920(16) 0.24197(13) -0.02653(12) 0.0559(4) Uani 1 1 d . . .
C2 C 1.12409(16) 0.24747(14) -0.01758(13) 0.0596(4) Uani 1 1 d . . .
C3 C 1.17567(15) 0.17373(14) 0.05858(13) 0.0584(4) Uani 1 1 d . . .
C4 C 1.08086(14) 0.12221(12) 0.09454(12) 0.0517(4) Uani 1 1 d . . .
C5 C 1.08077(14) 0.03878(13) 0.16427(12) 0.0551(4) Uani 1 1 d . . .
H5 H 1.1531 0.0074 0.1972 0.066 Uiso 1 1 calc R . .
C6 C 0.97588(14) -0.00113(13) 0.18794(11) 0.0535(4) Uani 1 1 d . . .
C7 C 0.95576(17) -0.08482(14) 0.25459(13) 0.0629(4) Uani 1 1 d . . .
H7 H 1.0132 -0.1302 0.2950 0.075 Uiso 1 1 calc R . .
C8 C 0.83493(17) -0.08767(15) 0.24942(13) 0.0658(4) Uani 1 1 d . . .
H8 H 0.7959 -0.1352 0.2861 0.079 Uiso 1 1 calc R . .
C9 C 0.78146(15) -0.00648(15) 0.17929(13) 0.0610(4) Uani 1 1 d . . .
C10 C 0.65253(18) 0.0257(2) 0.14491(18) 0.0876(7) Uani 1 1 d . . .
H10A H 0.6460 0.1063 0.1485 0.105 Uiso 1 1 calc R . .
H10B H 0.6244 0.0039 0.0737 0.105 Uiso 1 1 calc R . .
C11 C 0.57354(16) -0.02598(17) 0.20719(15) 0.0700(5) Uani 1 1 d U . .
C12 C 0.5032(2) -0.1149(2) 0.1721(2) 0.1075(8) Uani 1 1 d U . .
H12 H 0.5063 -0.1469 0.1094 0.129 Uiso 1 1 calc R . .
C13 C 0.4252(3) -0.1592(3) 0.2303(4) 0.1436(15) Uani 1 1 d U . .
H13 H 0.3760 -0.2196 0.2066 0.172 Uiso 1 1 calc R . .
C14 C 0.4248(3) -0.1113(5) 0.3202(4) 0.1482(17) Uani 1 1 d U . .
H14 H 0.3771 -0.1420 0.3608 0.178 Uiso 1 1 calc R . .
C15 C 0.4893(4) -0.0222(5) 0.3543(3) 0.1605(16) Uani 1 1 d U . .
H15 H 0.4827 0.0117 0.4155 0.193 Uiso 1 1 calc R . .
C16 C 0.5656(3) 0.0194(3) 0.2984(2) 0.1152(9) Uani 1 1 d U . .
H16 H 0.6132 0.0803 0.3236 0.138 Uiso 1 1 calc R . .
C17 C 0.90571(19) 0.30371(17) -0.10022(15) 0.0742(5) Uani 1 1 d . . .
H17A H 0.8828 0.2617 -0.1627 0.111 Uiso 1 1 calc R . .
H17B H 0.9363 0.3749 -0.1148 0.111 Uiso 1 1 calc R . .
H17C H 0.8376 0.3145 -0.0708 0.111 Uiso 1 1 calc R . .
C18 C 1.1846(2) 0.32369(17) -0.07939(16) 0.0773(5) Uani 1 1 d . . .
H18A H 1.1406 0.3231 -0.1503 0.093 Uiso 1 1 calc R . .
H18B H 1.2641 0.2958 -0.0776 0.093 Uiso 1 1 calc R . .
C19 C 1.1931(3) 0.4423(2) -0.0399(2) 0.1025(8) Uani 1 1 d . . .
H19A H 1.1153 0.4682 -0.0361 0.154 Uiso 1 1 calc R . .
H19B H 1.2246 0.4893 -0.0857 0.154 Uiso 1 1 calc R . .
H19C H 1.2448 0.4448 0.0272 0.154 Uiso 1 1 calc R . .
C20 C 1.30447(17) 0.1502(2) 0.09926(18) 0.0811(6) Uani 1 1 d . . .
H20A H 1.3503 0.1852 0.0561 0.122 Uiso 1 1 calc R . .
H20B H 1.3176 0.0711 0.1002 0.122 Uiso 1 1 calc R . .
H20C H 1.3286 0.1791 0.1678 0.122 Uiso 1 1 calc R . .
F1 F 0.76872(9) 0.11583(10) -0.02344(8) 0.0766(3) Uani 1 1 d . . .
F2 F 0.81149(10) 0.23809(8) 0.10862(9) 0.0751(3) Uani 1 1 d . . .
N1 N 0.97367(11) 0.16846(10) 0.04117(9) 0.0505(3) Uani 1 1 d . . .
N2 N 0.86724(12) 0.04616(11) 0.14222(10) 0.0526(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 F1 1.379(2) . ?
B1 F2 1.387(2) . ?
B1 N2 1.544(2) . ?
B1 N1 1.551(2) . ?
C1 N1 1.3410(19) . ?
C1 C2 1.417(2) . ?
C1 C17 1.485(3) . ?
C2 C3 1.379(2) . ?
C2 C18 1.502(2) . ?
C3 C4 1.426(2) . ?
C3 C20 1.488(3) . ?
C4 C5 1.367(2) . ?
C4 N1 1.3953(19) . ?
C5 C6 1.398(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.385(2) . ?
C6 C7 1.394(2) . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.354(2) . ?
C9 C10 1.503(3) . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.356(3) . ?
C11 C12 1.357(3) . ?
C12 C13 1.414(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.331(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.322(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.513(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
F1 B1 F2 109.71(14) . . ?
F1 B1 N2 110.37(13) . . ?
F2 B1 N2 110.08(13) . . ?
F1 B1 N1 110.43(13) . . ?
F2 B1 N1 109.05(13) . . ?
N2 B1 N1 107.16(13) . . ?
N1 C1 C2 110.09(15) . . ?
N1 C1 C17 122.66(16) . . ?
C2 C1 C17 127.23(16) . . ?
C3 C2 C1 107.16(14) . . ?
C3 C2 C18 128.29(17) . . ?
C1 C2 C18 124.53(17) . . ?
C2 C3 C4 106.84(15) . . ?
C2 C3 C20 128.46(16) . . ?
C4 C3 C20 124.69(16) . . ?
C5 C4 N1 120.31(14) . . ?
C5 C4 C3 131.49(15) . . ?
N1 C4 C3 108.15(14) . . ?
C4 C5 C6 122.39(15) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
N2 C6 C7 108.33(14) . . ?
N2 C6 C5 120.02(14) . . ?
C7 C6 C5 131.64(15) . . ?
C8 C7 C6 107.13(15) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 107.84(15) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C8 108.76(15) . . ?
N2 C9 C10 121.25(16) . . ?
C8 C9 C10 129.99(17) . . ?
C11 C10 C9 113.83(17) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C16 C11 C12 118.1(2) . . ?
C16 C11 C10 120.3(2) . . ?
C12 C11 C10 121.5(2) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 117.5(3) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C15 123.1(4) . . ?
C13 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C14 C15 C16 119.0(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 121.6(3) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 C19 112.49(17) . . ?
C2 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C2 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C4 107.73(13) . . ?
C1 N1 B1 127.66(13) . . ?
C4 N1 B1 124.42(12) . . ?
C9 N2 C6 107.93(13) . . ?
C9 N2 B1 127.07(14) . . ?
C6 N2 B1 124.97(13) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_160526b_0m
_database_code_depnum_ccdc_archive 'CCDC 1588356'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2016-05-27
_chemical_formula_sum            'C22 H16 B F2 N3 O2'
_chemical_formula_weight         403.190
_refine_ls_R_factor_all          0.091
_cell_length_a                   8.1055(10)
_cell_length_b                   10.4030(13)
_cell_length_c                   12.2541(15)
_cell_angle_alpha                73.386(1)
_cell_angle_beta                 89.110(2)
_cell_angle_gamma                85.852(2)
_cell_volume                     987.5(2)
_cell_formula_units_Z            2
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
B ? 1.200
C ? 1.200
H ? 1.200
F ? 1.200
N ? 1.200
O ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
B1 B 0.1870(3) 0.6413(2) 0.3175(2) 1.000 2 i ? d Uani 0.0494(5)
C1 C 0.1283(3) 0.8735(2) 0.1723(2) 1.000 2 i ? d Uani 0.0645(6)
H1 H 0.0348 0.8980 0.2087 1.000 2 i ? calc Uiso 0.07700
C2 C 0.1933(3) 0.9524(2) 0.0731(2) 1.000 2 i ? d Uani 0.0694(6)
H2 H 0.1521 1.0379 0.0315 1.000 2 i ? calc Uiso 0.08300
C3 C 0.3303(3) 0.8810(2) 0.0472(2) 1.000 2 i ? d Uani 0.0589(5)
H3 H 0.3990 0.9093 -0.0152 1.000 2 i ? calc Uiso 0.07100
C4 C 0.3474(2) 0.7581(2) 0.1320(2) 1.000 2 i ? d Uani 0.0464(5)
C5 C 0.4699(2) 0.6515(2) 0.1528(1) 1.000 2 i ? d Uani 0.0416(4)
C6 C 0.6114(2) 0.6593(2) 0.0735(2) 1.000 2 i ? d Uani 0.0434(4)
C7 C 0.5860(2) 0.6730(2) -0.0413(2) 1.000 2 i ? d Uani 0.0541(5)
H7 H 0.4791 0.6764 -0.0690 1.000 2 i ? calc Uiso 0.06500
C8 C 0.7189(3) 0.6815(2) -0.1148(2) 1.000 2 i ? d Uani 0.0572(5)
H8 H 0.7026 0.6906 -0.1917 1.000 2 i ? calc Uiso 0.06900
C9 C 0.8756(2) 0.6761(2) -0.0716(2) 1.000 2 i ? d Uani 0.0484(5)
C10 C 0.9046(2) 0.6630(2) 0.0403(2) 1.000 2 i ? d Uani 0.0509(5)
H10 H 1.0119 0.6597 0.0671 1.000 2 i ? calc Uiso 0.06100
C11 C 0.7716(2) 0.6546(2) 0.1132(2) 1.000 2 i ? d Uani 0.0484(5)
H11 H 0.7897 0.6457 0.1899 1.000 2 i ? calc Uiso 0.05800
C12 C 0.4642(2) 0.5425(2) 0.2487(1) 1.000 2 i ? d Uani 0.0416(4)
C13 C 0.5715(2) 0.4251(2) 0.2880(2) 1.000 2 i ? d Uani 0.0488(5)
H13 H 0.6691 0.4046 0.2537 1.000 2 i ? calc Uiso 0.05900
C14 C 0.5056(2) 0.3478(2) 0.3852(2) 1.000 2 i ? d Uani 0.0559(5)
H14 H 0.5500 0.2644 0.4291 1.000 2 i ? calc Uiso 0.06700
C15 C 0.3586(2) 0.4158(2) 0.4077(2) 1.000 2 i ? d Uani 0.0497(5)
C16 C 0.2410(3) 0.3725(2) 0.5049(2) 1.000 2 i ? d Uani 0.0704(7)
H16A H 0.2530 0.4265 0.5567 1.000 2 i ? calc Uiso 0.08400
H16B H 0.1287 0.3898 0.4755 1.000 2 i ? calc Uiso 0.08400
C17 C 0.2676(3) 0.2270(2) 0.5698(2) 1.000 2 i ? d Uani 0.0530(5)
C18 C 0.3929(3) 0.1812(2) 0.6468(2) 1.000 2 i ? d Uani 0.0780(7)
H18 H 0.4632 0.2426 0.6590 1.000 2 i ? calc Uiso 0.09400
C19 C 0.4198(4) 0.0492(3) 0.7071(2) 1.000 2 i ? d Uani 0.0975(9)
H19 H 0.5080 0.0215 0.7581 1.000 2 i ? calc Uiso 0.11700
C20 C 0.3180(4) -0.0400(3) 0.6922(3) 1.000 2 i ? d Uani 0.0978(9)
H20 H 0.3349 -0.1300 0.7336 1.000 2 i ? calc Uiso 0.11700
C21 C 0.1928(5) -0.0009(3) 0.6185(3) 1.000 2 i ? d Uani 0.1153(11)
H21 H 0.1232 -0.0638 0.6082 1.000 2 i ? calc Uiso 0.13800
C22 C 0.1652(3) 0.1351(3) 0.5560(3) 1.000 2 i ? d Uani 0.0931(9)
H22 H 0.0767 0.1622 0.5052 1.000 2 i ? calc Uiso 0.11200
F3 F 0.1846(2) 0.6865(1) 0.4117(1) 1.000 2 i ? d Uani 0.0754(4)
F4 F 0.0401(1) 0.5881(1) 0.3070(1) 1.000 2 i ? d Uani 0.0751(4)
N1 N 0.2194(2) 0.7559(2) 0.2089(1) 1.000 2 i ? d Uani 0.0492(4)
N2 N 0.3337(2) 0.5330(1) 0.3259(1) 1.000 2 i ? d Uani 0.0424(4)
N3 N 1.0174(3) 0.6865(2) -0.1496(2) 1.000 2 i ? d Uani 0.0649(5)
O1 O 0.9909(2) 0.7021(2) -0.2494(2) 1.000 2 i ? d Uani 0.1025(7)
O2 O 1.1553(2) 0.6774(2) -0.1091(2) 1.000 2 i ? d Uani 0.0887(6)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F3 . . 1.365(3) no
B1 F4 . . 1.371(2) no
B1 N1 . . 1.546(3) no
B1 N2 . . 1.561(3) no
C1 N1 . . 1.344(2) no
C1 C2 . . 1.379(3) no
C1 H1 . . 0.9300 no
C2 C3 . . 1.374(3) no
C2 H2 . . 0.9300 no
C3 C4 . . 1.397(3) no
C3 H3 . . 0.9300 no
C4 N1 . . 1.387(2) no
C4 C5 . . 1.403(3) no
C5 C12 . . 1.383(2) no
C5 C6 . . 1.483(2) no
C6 C11 . . 1.386(2) no
C6 C7 . . 1.390(3) no
C7 C8 . . 1.385(3) no
C7 H7 . . 0.9300 no
C8 C9 . . 1.374(3) no
C8 H8 . . 0.9300 no
C9 C10 . . 1.361(3) no
C9 N3 . . 1.474(2) no
C10 C11 . . 1.381(2) no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 N2 . . 1.398(2) no
C12 C13 . . 1.415(2) no
C13 C14 . . 1.358(3) no
C13 H13 . . 0.9300 no
C14 C15 . . 1.406(3) no
C14 H14 . . 0.9300 no
C15 N2 . . 1.344(2) no
C15 C16 . . 1.500(3) no
C16 C17 . . 1.497(3) no
C16 H16A . . 0.9700 no
C16 H16B . . 0.9700 no
C17 C22 . . 1.358(3) no
C17 C18 . . 1.361(3) no
C18 C19 . . 1.365(3) no
C18 H18 . . 0.9300 no
C19 C20 . . 1.337(4) no
C19 H19 . . 0.9300 no
C20 C21 . . 1.331(4) no
C20 H20 . . 0.9300 no
C21 C22 . . 1.406(4) no
C21 H21 . . 0.9300 no
C22 H22 . . 0.9300 no
N3 O1 . . 1.207(2) no
N3 O2 . . 1.216(2) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F3 B1 F4 . . . 110.19(17) no
F3 B1 N1 . . . 110.97(17) no
F4 B1 N1 . . . 109.94(16) no
F3 B1 N2 . . . 110.03(16) no
F4 B1 N2 . . . 110.08(17) no
N1 B1 N2 . . . 105.53(15) no
N1 C1 C2 . . . 110.30(19) no
N1 C1 H1 . . . 124.90 no
C2 C1 H1 . . . 124.90 no
C3 C2 C1 . . . 107.12(19) no
C3 C2 H2 . . . 126.40 no
C1 C2 H2 . . . 126.40 no
C2 C3 C4 . . . 107.47(19) no
C2 C3 H3 . . . 126.30 no
C4 C3 H3 . . . 126.30 no
N1 C4 C3 . . . 107.83(17) no
N1 C4 C5 . . . 120.04(16) no
C3 C4 C5 . . . 131.97(18) no
C12 C5 C4 . . . 120.86(16) no
C12 C5 C6 . . . 119.73(16) no
C4 C5 C6 . . . 119.34(15) no
C11 C6 C7 . . . 119.07(17) no
C11 C6 C5 . . . 120.05(16) no
C7 C6 C5 . . . 120.88(16) no
C8 C7 C6 . . . 120.41(18) no
C8 C7 H7 . . . 119.80 no
C6 C7 H7 . . . 119.80 no
C9 C8 C7 . . . 118.52(18) no
C9 C8 H8 . . . 120.70 no
C7 C8 H8 . . . 120.70 no
C10 C9 C8 . . . 122.51(17) no
C10 C9 N3 . . . 118.73(18) no
C8 C9 N3 . . . 118.76(18) no
C9 C10 C11 . . . 118.76(17) no
C9 C10 H10 . . . 120.60 no
C11 C10 H10 . . . 120.60 no
C10 C11 C6 . . . 120.74(18) no
C10 C11 H11 . . . 119.60 no
C6 C11 H11 . . . 119.60 no
C5 C12 N2 . . . 121.13(16) no
C5 C12 C13 . . . 131.32(16) no
N2 C12 C13 . . . 107.53(15) no
C14 C13 C12 . . . 107.34(16) no
C14 C13 H13 . . . 126.30 no
C12 C13 H13 . . . 126.30 no
C13 C14 C15 . . . 108.05(17) no
C13 C14 H14 . . . 126.00 no
C15 C14 H14 . . . 126.00 no
N2 C15 C14 . . . 109.23(16) no
N2 C15 C16 . . . 122.18(16) no
C14 C15 C16 . . . 128.59(18) no
C17 C16 C15 . . . 113.49(17) no
C17 C16 H16A . . . 108.90 no
C15 C16 H16A . . . 108.90 no
C17 C16 H16B . . . 108.90 no
C15 C16 H16B . . . 108.90 no
H16A C16 H16B . . . 107.70 no
C22 C17 C18 . . . 117.0(2) no
C22 C17 C16 . . . 121.2(2) no
C18 C17 C16 . . . 121.7(2) no
C17 C18 C19 . . . 122.9(2) no
C17 C18 H18 . . . 118.60 no
C19 C18 H18 . . . 118.60 no
C20 C19 C18 . . . 119.3(3) no
C20 C19 H19 . . . 120.40 no
C18 C19 H19 . . . 120.40 no
C21 C20 C19 . . . 120.5(3) no
C21 C20 H20 . . . 119.80 no
C19 C20 H20 . . . 119.80 no
C20 C21 C22 . . . 120.3(3) no
C20 C21 H21 . . . 119.80 no
C22 C21 H21 . . . 119.80 no
C17 C22 C21 . . . 120.0(3) no
C17 C22 H22 . . . 120.00 no
C21 C22 H22 . . . 120.00 no
C1 N1 C4 . . . 107.28(16) no
C1 N1 B1 . . . 125.80(17) no
C4 N1 B1 . . . 126.91(15) no
C15 N2 C12 . . . 107.85(14) no
C15 N2 B1 . . . 126.74(15) no
C12 N2 B1 . . . 125.41(14) no
O1 N3 O2 . . . 123.7(2) no
O1 N3 C9 . . . 118.6(2) no
O2 N3 C9 . . . 117.8(2) no
