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

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

data_compound9
_database_code_depnum_ccdc_archive 'CCDC 1042619'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2014-12-19
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H13 B F10 N2'
_chemical_formula_sum            'C21 H13 B F10 N2'
_chemical_formula_weight         494.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H13 B F10 N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   12.0013(3)
_cell_length_b                   11.1213(2)
_cell_length_c                   14.8617(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.860(2)
_cell_angle_gamma                90
_cell_volume                     1979.09(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21556
_cell_measurement_temperature    94.98(13)
_cell_measurement_theta_max      32.0060
_cell_measurement_theta_min      3.2860
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  3.730
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28c (release 15-05-2013 CrysAlis171 .NET)
(compiled May 15 2013,09:16:53)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.0875
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            61610
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_min         2.747
_diffrn_ambient_temperature      94.98(13)
_diffrn_detector_area_resol_mean 8.0951
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489    0.0000  -90.0000 132

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489  -38.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489   77.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega    7.00   65.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489  -99.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega   -4.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489   77.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega   30.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489 -137.0000 -152.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   26.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489 -133.0000   25.0000 59

#__ type_ start__ end____ width___ exp.time_
  8 omega    6.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489   57.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega    6.00   57.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489   57.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 10 omega  -46.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489    0.0000   60.0000 139

#__ type_ start__ end____ width___ exp.time_
 11 omega    6.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489   57.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
 12 omega    6.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489   57.0000   90.0000 87

#__ type_ start__ end____ width___ exp.time_
 13 omega    7.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489 -133.0000   25.0000 78

#__ type_ start__ end____ width___ exp.time_
 14 omega   -4.00   94.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489   77.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489  178.0000 -180.0000 60

#__ type_ start__ end____ width___ exp.time_
 16 omega  -43.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       24.9489  -57.0000  150.0000 86
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0484594000
_diffrn_orient_matrix_UB_12      0.0081705000
_diffrn_orient_matrix_UB_13      -0.0241030000
_diffrn_orient_matrix_UB_21      -0.0330539000
_diffrn_orient_matrix_UB_22      -0.0036988000
_diffrn_orient_matrix_UB_23      -0.0413275000
_diffrn_orient_matrix_UB_31      -0.0082224000
_diffrn_orient_matrix_UB_32      0.0631344000
_diffrn_orient_matrix_UB_33      0.0007000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5034
_reflns_number_total             5765
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28c (release 15-05-2013 CrysAlis171 .NET)
(compiled May 15 2013,09:16:53)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28c (release 15-05-2013 CrysAlis171 .NET)
(compiled May 15 2013,09:16:53)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28c (release 15-05-2013 CrysAlis171 .NET)
(compiled May 15 2013,09:16:53)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0509P)²+1.1848P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1084
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
B1 B 0.38684(10) 0.12604(12) 0.36808(9) 0.0135(2) Uani 1 1 d . . . . .
C1 C 0.22906(9) 0.03652(10) 0.38139(8) 0.0133(2) Uani 1 1 d . . . . .
C2 C 0.12092(10) -0.00193(11) 0.38487(8) 0.0148(2) Uani 1 1 d . . . . .
H2 H 0.1053(15) -0.0813(17) 0.4015(12) 0.023(4) Uiso 1 1 d . . . . .
C3 C 0.03371(9) 0.08386(11) 0.36818(8) 0.0148(2) Uani 1 1 d . . . . .
C4 C 0.06517(10) 0.20537(11) 0.35335(8) 0.0152(2) Uani 1 1 d . . . . .
H4 H 0.0107(15) 0.2654(16) 0.3457(12) 0.023(4) Uiso 1 1 d . . . . .
C5 C 0.17560(9) 0.23785(11) 0.34918(8) 0.0138(2) Uani 1 1 d . . . . .
C6 C 0.34592(10) -0.01011(11) 0.40186(9) 0.0159(2) Uani 1 1 d . . . . .
H6A H 0.3611(14) -0.0274(16) 0.4658(12) 0.019(4) Uiso 1 1 d . . . . .
H6B H 0.3638(15) -0.0831(18) 0.3666(13) 0.026(5) Uiso 1 1 d . . . . .
C7 C 0.21318(11) 0.36530(11) 0.33911(9) 0.0187(2) Uani 1 1 d . . . . .
H7A H 0.2464(17) 0.395(2) 0.3947(15) 0.041(6) Uiso 1 1 d . . . . .
H7B H 0.2691(17) 0.3698(18) 0.2965(14) 0.035(5) Uiso 1 1 d . . . . .
H7C H 0.1533(19) 0.415(2) 0.3206(16) 0.046(6) Uiso 1 1 d . . . . .
C8 C -0.10347(11) -0.07775(13) 0.36869(10) 0.0220(3) Uani 1 1 d . . . . .
H8A H -0.1817(17) -0.0859(18) 0.3517(13) 0.030(5) Uiso 1 1 d . . . . .
H8B H -0.0633(16) -0.1219(17) 0.3229(13) 0.028(5) Uiso 1 1 d . . . . .
H8C H -0.0885(16) -0.1127(18) 0.4282(14) 0.030(5) Uiso 1 1 d . . . . .
C9 C -0.16729(10) 0.13449(13) 0.36593(9) 0.0203(2) Uani 1 1 d . . . . .
H9A H -0.2021(17) 0.1409(18) 0.3072(14) 0.033(5) Uiso 1 1 d . . . . .
H9B H -0.1443(17) 0.215(2) 0.3853(14) 0.039(5) Uiso 1 1 d . . . . .
H9C H -0.2234(19) 0.105(2) 0.4044(15) 0.044(6) Uiso 1 1 d . . . . .
C10 C 0.44340(9) 0.11638(11) 0.27210(8) 0.0146(2) Uani 1 1 d . . . . .
C11 C 0.54049(10) 0.04804(11) 0.26858(8) 0.0170(2) Uani 1 1 d . . . . .
C12 C 0.59572(10) 0.02797(12) 0.19118(9) 0.0193(2) Uani 1 1 d . . . . .
C13 C 0.55362(11) 0.07874(12) 0.11090(9) 0.0197(2) Uani 1 1 d . . . . .
C14 C 0.45682(11) 0.14554(11) 0.10991(8) 0.0183(2) Uani 1 1 d . . . . .
C15 C 0.40360(10) 0.16260(11) 0.18919(8) 0.0158(2) Uani 1 1 d . . . . .
C16 C 0.44969(9) 0.21564(11) 0.44226(8) 0.0145(2) Uani 1 1 d . . . . .
C17 C 0.54703(10) 0.28155(11) 0.43226(8) 0.0163(2) Uani 1 1 d . . . . .
C18 C 0.59556(10) 0.35764(12) 0.49813(9) 0.0198(2) Uani 1 1 d . . . . .
C19 C 0.54620(11) 0.37170(13) 0.57870(9) 0.0226(3) Uani 1 1 d . . . . .
C20 C 0.44895(11) 0.30986(13) 0.59204(9) 0.0220(3) Uani 1 1 d . . . . .
C21 C 0.40376(10) 0.23499(12) 0.52479(8) 0.0177(2) Uani 1 1 d . . . . .
F1 F 0.58575(6) -0.00270(8) 0.34551(5) 0.02194(17) Uani 1 1 d . . . . .
F2 F 0.68874(7) -0.03950(9) 0.19291(6) 0.02829(19) Uani 1 1 d . . . . .
F3 F 0.60625(7) 0.06323(9) 0.03490(6) 0.0286(2) Uani 1 1 d . . . . .
F4 F 0.41530(8) 0.19531(8) 0.03236(5) 0.02697(19) Uani 1 1 d . . . . .
F5 F 0.30832(7) 0.22750(7) 0.18152(5) 0.02153(17) Uani 1 1 d . . . . .
F6 F 0.60063(6) 0.27544(8) 0.35519(5) 0.02355(18) Uani 1 1 d . . . . .
F7 F 0.68916(7) 0.41891(9) 0.48370(6) 0.0305(2) Uani 1 1 d . . . . .
F8 F 0.59086(8) 0.44530(9) 0.64272(6) 0.0352(2) Uani 1 1 d . . . . .
F9 F 0.39835(8) 0.32389(10) 0.66907(6) 0.0361(2) Uani 1 1 d . . . . .
F10 F 0.30755(6) 0.17959(8) 0.54242(5) 0.02418(18) Uani 1 1 d . . . . .
N1 N 0.25477(8) 0.15129(9) 0.35907(7) 0.01276(18) Uani 1 1 d . . . . .
N2 N -0.07440(8) 0.04969(10) 0.36891(8) 0.0185(2) 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 C6 1.6790(18) . ?
B1 C10 1.6239(18) . ?
B1 C16 1.6327(18) . ?
B1 N1 1.6065(16) . ?
C1 C2 1.3706(15) . ?
C1 C6 1.5070(16) . ?
C1 N1 1.3596(15) . ?
C2 H2 0.939(19) . ?
C2 C3 1.4257(17) . ?
C3 C4 1.4242(17) . ?
C3 N2 1.3527(14) . ?
C4 H4 0.936(18) . ?
C4 C5 1.3791(16) . ?
C5 C7 1.4980(17) . ?
C5 N1 1.3536(15) . ?
C6 H6A 0.975(18) . ?
C6 H6B 0.997(19) . ?
C7 H7A 0.95(2) . ?
C7 H7B 0.95(2) . ?
C7 H7C 0.94(2) . ?
C8 H8A 0.96(2) . ?
C8 H8B 0.99(2) . ?
C8 H8C 0.97(2) . ?
C8 N2 1.4595(17) . ?
C9 H9A 0.95(2) . ?
C9 H9B 0.98(2) . ?
C9 H9C 0.97(2) . ?
C9 N2 1.4585(17) . ?
C10 C11 1.3951(16) . ?
C10 C15 1.3898(17) . ?
C11 C12 1.3838(17) . ?
C11 F1 1.3553(14) . ?
C12 C13 1.3844(19) . ?
C12 F2 1.3439(14) . ?
C13 C14 1.3782(18) . ?
C13 F3 1.3418(14) . ?
C14 C15 1.3906(17) . ?
C14 F4 1.3438(15) . ?
C15 F5 1.3505(14) . ?
C16 C17 1.3955(16) . ?
C16 C21 1.3948(17) . ?
C17 C18 1.3918(18) . ?
C17 F6 1.3525(14) . ?
C18 C19 1.3800(19) . ?
C18 F7 1.3434(14) . ?
C19 C20 1.3805(18) . ?
C19 F8 1.3393(15) . ?
C20 C21 1.3832(18) . ?
C20 F9 1.3405(15) . ?
C21 F10 1.3499(13) . ?

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
C10 B1 C6 110.55(10) . . ?
C10 B1 C16 115.60(9) . . ?
C16 B1 C6 118.67(10) . . ?
N1 B1 C6 82.87(8) . . ?
N1 B1 C10 114.00(10) . . ?
N1 B1 C16 110.98(9) . . ?
C2 C1 C6 139.08(11) . . ?
N1 C1 C2 122.22(11) . . ?
N1 C1 C6 98.56(9) . . ?
C1 C2 H2 120.6(11) . . ?
C1 C2 C3 118.07(11) . . ?
C3 C2 H2 121.2(11) . . ?
C4 C3 C2 117.57(10) . . ?
N2 C3 C2 120.26(11) . . ?
N2 C3 C4 122.16(11) . . ?
C3 C4 H4 120.3(11) . . ?
C5 C4 C3 121.41(11) . . ?
C5 C4 H4 118.3(11) . . ?
C4 C5 C7 123.30(11) . . ?
N1 C5 C4 118.58(11) . . ?
N1 C5 C7 118.03(10) . . ?
B1 C6 H6A 115.5(10) . . ?
B1 C6 H6B 120.0(11) . . ?
C1 C6 B1 85.20(8) . . ?
C1 C6 H6A 112.0(10) . . ?
C1 C6 H6B 113.9(11) . . ?
H6A C6 H6B 108.6(15) . . ?
C5 C7 H7A 110.8(13) . . ?
C5 C7 H7B 110.2(12) . . ?
C5 C7 H7C 111.3(14) . . ?
H7A C7 H7B 106.5(18) . . ?
H7A C7 H7C 108.3(19) . . ?
H7B C7 H7C 109.5(18) . . ?
H8A C8 H8B 106.6(16) . . ?
H8A C8 H8C 108.6(16) . . ?
H8B C8 H8C 111.0(16) . . ?
N2 C8 H8A 108.8(12) . . ?
N2 C8 H8B 110.9(11) . . ?
N2 C8 H8C 110.9(12) . . ?
H9A C9 H9B 107.6(17) . . ?
H9A C9 H9C 106.8(18) . . ?
H9B C9 H9C 109.4(18) . . ?
N2 C9 H9A 111.5(12) . . ?
N2 C9 H9B 112.6(12) . . ?
N2 C9 H9C 108.8(13) . . ?
C11 C10 B1 117.94(10) . . ?
C15 C10 B1 127.97(10) . . ?
C15 C10 C11 113.97(11) . . ?
C12 C11 C10 124.55(12) . . ?
F1 C11 C10 118.91(11) . . ?
F1 C11 C12 116.54(11) . . ?
C11 C12 C13 118.89(11) . . ?
F2 C12 C11 121.19(12) . . ?
F2 C12 C13 119.91(11) . . ?
C14 C13 C12 119.18(11) . . ?
F3 C13 C12 120.52(12) . . ?
F3 C13 C14 120.30(12) . . ?
C13 C14 C15 119.97(12) . . ?
F4 C14 C13 119.66(11) . . ?
F4 C14 C15 120.37(11) . . ?
C10 C15 C14 123.42(11) . . ?
F5 C15 C10 120.73(11) . . ?
F5 C15 C14 115.85(11) . . ?
C17 C16 B1 126.91(10) . . ?
C21 C16 B1 119.73(10) . . ?
C21 C16 C17 113.33(11) . . ?
C18 C17 C16 123.92(11) . . ?
F6 C17 C16 120.87(11) . . ?
F6 C17 C18 115.20(10) . . ?
C19 C18 C17 119.70(11) . . ?
F7 C18 C17 120.73(11) . . ?
F7 C18 C19 119.57(11) . . ?
C18 C19 C20 118.99(12) . . ?
F8 C19 C18 120.73(12) . . ?
F8 C19 C20 120.27(12) . . ?
C19 C20 C21 119.35(12) . . ?
F9 C20 C19 120.05(12) . . ?
F9 C20 C21 120.59(12) . . ?
C20 C21 C16 124.70(11) . . ?
F10 C21 C16 119.61(11) . . ?
F10 C21 C20 115.68(11) . . ?
C1 N1 B1 93.12(9) . . ?
C5 N1 B1 144.57(10) . . ?
C5 N1 C1 121.67(10) . . ?
C3 N2 C8 120.13(11) . . ?
C3 N2 C9 123.34(11) . . ?
C9 N2 C8 116.47(10) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 1 0.0437 -1.0000 -0.0000 1.0000 -0.0726 -0.0083 0.0089
1 -2 1 0.1781 1.0000 -2.0000 1.0000 0.0080 -0.0670 -0.1338
0 1 0 0.2970 0.0000 1.0000 -0.0000 0.0082 -0.0037 0.0631
1 0 -1 0.0437 1.0000 0.0000 -1.0000 0.0726 0.0083 -0.0089
0 -1 -1 0.4001 -0.0000 -1.0000 -1.0000 0.0159 0.0450 -0.0638
7 11 12 0.3105 7.0000 11.0000 12.0000 0.1399 -0.7680 0.6453
3 14 7 0.2866 3.0000 14.0000 7.0000 0.0910 -0.4402 0.8641
-10 6 -15 0.1709 -9.9999 6.0000 -15.0002 -0.0740 0.9283 0.4505

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-2
####################################################################### 
# 
# 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_compound19
_database_code_depnum_ccdc_archive 'CCDC 1042620'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

_audit_creation_date             2013-12-04
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H14 B F10 N'
_chemical_formula_sum            'C22 H14 B F10 N'
_chemical_formula_weight         493.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H14 B F10 N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   11.2973(2)
_cell_length_b                   13.7505(2)
_cell_length_c                   12.6885(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.5752(17)
_cell_angle_gamma                90
_cell_volume                     1958.11(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21296
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      30.0370
_cell_measurement_theta_min      3.3790
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.2696
_exptl_crystal_size_mid          0.2259
_exptl_crystal_size_min          0.0311
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            55604
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         2.564
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector_area_resol_mean 8.0951
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00  -35.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -      -18.8719 -178.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00    1.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -      -18.8719  -38.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00  -13.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -      -18.8719  144.0000  122.9826 73

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   88.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -       18.8719   77.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00   37.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -       18.8719  -57.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega  -53.00   54.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -       18.8719  -19.0000 -120.0000 107

#__ type_ start__ end____ width___ exp.time_
  7 omega    6.00   87.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -       18.8719   57.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega   -4.00   70.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -       18.8719 -118.0000   10.4767 74

#__ type_ start__ end____ width___ exp.time_
  9 omega  -10.00   75.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -       18.8719   77.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 10 omega  -86.00  -12.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -      -18.8719  144.0000  -33.1467 74

#__ type_ start__ end____ width___ exp.time_
 11 omega  -87.00    0.00   1.0000   37.5200
omega____ theta____ kappa____ phi______ frames
    -      -18.8719  -57.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00   79.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8579    0.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega   62.00  100.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8579 -178.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 14 omega  -46.00   23.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8579    0.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
 15 omega    6.00   93.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8579   57.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
 16 omega  -46.00   76.00   1.0000   64.0000
omega____ theta____ kappa____ phi______ frames
    -       24.8579    0.0000  150.0000 122
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0227450000
_diffrn_orient_matrix_UB_12      -0.0480786000
_diffrn_orient_matrix_UB_13      -0.0047070000
_diffrn_orient_matrix_UB_21      0.0372939000
_diffrn_orient_matrix_UB_22      -0.0098700000
_diffrn_orient_matrix_UB_23      -0.0400309000
_diffrn_orient_matrix_UB_31      0.0457119000
_diffrn_orient_matrix_UB_32      -0.0158319000
_diffrn_orient_matrix_UB_33      0.0392534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4928
_reflns_number_total             5687
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5687
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0292P)²+1.5049P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          
;
 Disorder of N(1), C(1) to C(10) over two positions (55:45).
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
F1 F 0.37443(7) 0.61617(6) 0.55734(6) 0.01955(16) Uani 1 1 d . . . . .
F2 F 0.42113(8) 0.42766(6) 0.55097(6) 0.02232(17) Uani 1 1 d . . . . .
F3 F 0.57504(8) 0.34223(6) 0.70531(7) 0.02727(19) Uani 1 1 d . . . . .
F4 F 0.67172(8) 0.45128(6) 0.87312(7) 0.02769(19) Uani 1 1 d . . . . .
F5 F 0.62841(8) 0.63904(6) 0.88206(7) 0.02614(19) Uani 1 1 d . . . . .
F6 F 0.41439(8) 0.70784(7) 0.94600(7) 0.02802(19) Uani 1 1 d . . . . .
F7 F 0.49821(8) 0.80266(7) 1.12106(7) 0.0304(2) Uani 1 1 d . . . . .
F8 F 0.64230(8) 0.96036(7) 1.11117(7) 0.0283(2) Uani 1 1 d . . . . .
F9 F 0.69662(8) 1.02289(6) 0.91838(7) 0.0291(2) Uani 1 1 d . . . . .
F10 F 0.61337(8) 0.93318(6) 0.74251(6) 0.02288(17) Uani 1 1 d . . . . .
N1 N 0.4802(17) 0.808(2) 0.6182(16) 0.0159(4) Uani 0.5542(19) 1 d D . P A 1
C1 C 0.5817(13) 0.7881(15) 0.5736(10) 0.0182(13) Uani 0.5542(19) 1 d D . P A 1
C2 C 0.5861(6) 0.8045(8) 0.4656(7) 0.0259(12) Uani 0.5542(19) 1 d D . P A 1
H2 H 0.6476 0.7781 0.4319 0.031 Uiso 0.5542(19) 1 calc R U P A 1
C3 C 0.4987(6) 0.8602(8) 0.4085(7) 0.0291(12) Uani 0.5542(19) 1 d D . P A 1
H3 H 0.4985 0.8700 0.3360 0.035 Uiso 0.5542(19) 1 calc R U P A 1
C4 C 0.4119(6) 0.9005(3) 0.4631(4) 0.0228(8) Uani 0.5542(19) 1 d D . P A 1
H4 H 0.3568 0.9434 0.4285 0.027 Uiso 0.5542(19) 1 calc R U P A 1
C5 C 0.4059(5) 0.8779(3) 0.5684(4) 0.0177(7) Uani 0.5542(19) 1 d D . P A 1
C6 C 0.3284(2) 0.94003(18) 0.63155(19) 0.0201(3) Uani 0.5542(19) 1 d D . P A 1
H6A H 0.3129 1.0004 0.5928 0.024 Uiso 0.5542(19) 1 calc R U P A 1
H6B H 0.3757 0.9565 0.6978 0.024 Uiso 0.5542(19) 1 calc R U P A 1
C7 C 0.2087(2) 0.90208(18) 0.6592(2) 0.0203(4) Uani 0.5542(19) 1 d D . P A 1
H7A H 0.1607 0.9563 0.6784 0.024 Uiso 0.5542(19) 1 calc R U P A 1
H7B H 0.1667 0.8708 0.5973 0.024 Uiso 0.5542(19) 1 calc R U P A 1
C8 C 0.2243(8) 0.8297(7) 0.7507(7) 0.0185(11) Uani 0.5542(19) 1 d D . P A 1
H8A H 0.2626 0.8618 0.8137 0.022 Uiso 0.5542(19) 1 calc R U P A 1
H8B H 0.1468 0.8070 0.7659 0.022 Uiso 0.5542(19) 1 calc R U P A 1
C9 C 0.2995(17) 0.7433(10) 0.7235(16) 0.0163(15) Uani 0.5542(19) 1 d D . P A 1
H9A H 0.2697 0.7227 0.6523 0.020 Uiso 0.5542(19) 1 calc R U P A 1
H9B H 0.2837 0.6906 0.7709 0.020 Uiso 0.5542(19) 1 calc R U P A 1
C10 C 0.6837(10) 0.7324(9) 0.6331(6) 0.0214(12) Uani 0.5542(19) 1 d D . P A 1
H10A H 0.6850 0.7440 0.7078 0.032 Uiso 0.5542(19) 1 calc R U P A 1
H10B H 0.7575 0.7538 0.6101 0.032 Uiso 0.5542(19) 1 calc R U P A 1
H10C H 0.6734 0.6642 0.6190 0.032 Uiso 0.5542(19) 1 calc R U P A 1
N1B N 0.486(2) 0.804(3) 0.618(2) 0.0159(4) Uani 0.4458(19) 1 d D . P A 2
C1B C 0.5891(16) 0.775(2) 0.5814(13) 0.0182(13) Uani 0.4458(19) 1 d D . P A 2
C2B C 0.6160(8) 0.8057(10) 0.4819(9) 0.0259(12) Uani 0.4458(19) 1 d D . P A 2
H2B H 0.6923 0.7970 0.4629 0.031 Uiso 0.4458(19) 1 calc R U P A 2
C3B C 0.5306(9) 0.8486(11) 0.4130(10) 0.0291(12) Uani 0.4458(19) 1 d D . P A 2
H3B H 0.5432 0.8590 0.3427 0.035 Uiso 0.4458(19) 1 calc R U P A 2
C4B C 0.4260(8) 0.8761(5) 0.4487(6) 0.0228(8) Uani 0.4458(19) 1 d D . P A 2
H4B H 0.3698 0.9104 0.4039 0.027 Uiso 0.4458(19) 1 calc R U P A 2
C5B C 0.4024(7) 0.8534(4) 0.5513(6) 0.0177(7) Uani 0.4458(19) 1 d D . P A 2
C6B C 0.2865(3) 0.8936(2) 0.5823(2) 0.0201(3) Uani 0.4458(19) 1 d D . P A 2
H6BA H 0.2251 0.8450 0.5647 0.024 Uiso 0.4458(19) 1 calc R U P A 2
H6BB H 0.2653 0.9500 0.5382 0.024 Uiso 0.4458(19) 1 calc R U P A 2
C7B C 0.2824(3) 0.9233(2) 0.6971(2) 0.0203(4) Uani 0.4458(19) 1 d D . P A 2
H7BA H 0.2259 0.9761 0.7000 0.024 Uiso 0.4458(19) 1 calc R U P A 2
H7BB H 0.3602 0.9468 0.7263 0.024 Uiso 0.4458(19) 1 calc R U P A 2
C8B C 0.2463(11) 0.8389(9) 0.7641(8) 0.0185(11) Uani 0.4458(19) 1 d D . P A 2
H8BA H 0.1607 0.8296 0.7521 0.022 Uiso 0.4458(19) 1 calc R U P A 2
H8BB H 0.2678 0.8531 0.8387 0.022 Uiso 0.4458(19) 1 calc R U P A 2
C9B C 0.310(2) 0.7465(13) 0.734(2) 0.0163(15) Uani 0.4458(19) 1 d D . P A 2
H9BA H 0.2720 0.7247 0.6657 0.020 Uiso 0.4458(19) 1 calc R U P A 2
H9BB H 0.2961 0.6965 0.7855 0.020 Uiso 0.4458(19) 1 calc R U P A 2
C10B C 0.6917(13) 0.7378(12) 0.6574(8) 0.0214(12) Uani 0.4458(19) 1 d D . P A 2
H10D H 0.6762 0.7506 0.7289 0.032 Uiso 0.4458(19) 1 calc R U P A 2
H10E H 0.7636 0.7704 0.6439 0.032 Uiso 0.4458(19) 1 calc R U P A 2
H10F H 0.7006 0.6691 0.6478 0.032 Uiso 0.4458(19) 1 calc R U P A 2
C11 C 0.49278(11) 0.63884(9) 0.72346(10) 0.0163(2) Uani 1 1 d . . . . .
C12 C 0.44592(11) 0.57859(9) 0.64049(10) 0.0162(2) Uani 1 1 d . . . . .
C13 C 0.47080(12) 0.48035(9) 0.63343(10) 0.0178(2) Uani 1 1 d . . . . .
C14 C 0.54804(12) 0.43670(9) 0.71131(11) 0.0201(3) Uani 1 1 d . . . . .
C15 C 0.59690(12) 0.49222(10) 0.79573(11) 0.0204(3) Uani 1 1 d . . . . .
C16 C 0.56938(12) 0.59022(10) 0.79940(11) 0.0190(2) Uani 1 1 d . . . . .
C17 C 0.50849(11) 0.81379(9) 0.83282(10) 0.0157(2) Uani 1 1 d . . . . .
C18 C 0.48338(12) 0.78683(10) 0.93392(11) 0.0193(2) Uani 1 1 d . . . . .
C19 C 0.52670(12) 0.83365(10) 1.02671(10) 0.0212(3) Uani 1 1 d . . . . .
C20 C 0.60019(12) 0.91332(10) 1.02218(11) 0.0204(3) Uani 1 1 d . . . . .
C21 C 0.62749(12) 0.94440(9) 0.92498(11) 0.0195(3) Uani 1 1 d . . . . .
C22 C 0.58177(11) 0.89526(9) 0.83378(10) 0.0166(2) Uani 1 1 d . . . . .
B1 B 0.44853(12) 0.75357(10) 0.72810(11) 0.0153(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.3554(15) . ?
F2 C13 1.3416(15) . ?
F3 C14 1.3385(15) . ?
F4 C15 1.3437(16) . ?
F5 C16 1.3548(15) . ?
F6 C18 1.3557(15) . ?
F7 C19 1.3441(15) . ?
F8 C20 1.3404(15) . ?
F9 C21 1.3405(15) . ?
F10 C22 1.3547(15) . ?
N1 C1 1.363(8) . ?
N1 C5 1.382(10) . ?
N1 B1 1.657(13) . ?
C1 C2 1.396(9) . ?
C1 C10 1.512(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(7) . ?
C5 C6 1.517(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.524(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.523(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 B1 1.68(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1B C1B 1.370(10) . ?
N1B C5B 1.372(11) . ?
N1B B1 1.653(16) . ?
C1B C2B 1.397(11) . ?
C1B C10B 1.507(11) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.360(9) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.367(9) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.394(9) . ?
C5B C6B 1.514(7) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C6B C7B 1.519(4) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7B C8B 1.521(9) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C8B C9B 1.527(11) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C9B B1 1.58(2) . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C11 C12 1.3954(18) . ?
C11 C16 1.3904(18) . ?
C11 B1 1.6580(19) . ?
C12 C13 1.3848(18) . ?
C13 C14 1.3786(19) . ?
C14 C15 1.3783(19) . ?
C15 C16 1.3849(19) . ?
C17 C18 1.3952(18) . ?
C17 C22 1.3923(17) . ?
C17 B1 1.6444(18) . ?
C18 C19 1.3815(19) . ?
C19 C20 1.380(2) . ?
C20 C21 1.373(2) . ?
C21 C22 1.3876(18) . ?

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
C1 N1 C5 116.4(10) . . ?
C1 N1 B1 122.2(8) . . ?
C5 N1 B1 121.4(7) . . ?
N1 C1 C2 120.1(9) . . ?
N1 C1 C10 121.6(8) . . ?
C2 C1 C10 117.4(8) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(8) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.7(7) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(6) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C6 120.5(9) . . ?
C4 C5 N1 120.3(7) . . ?
C4 C5 C6 118.7(4) . . ?
C5 C6 H6A 107.2 . . ?
C5 C6 H6B 107.2 . . ?
C5 C6 C7 120.6(3) . . ?
H6A C6 H6B 106.8 . . ?
C7 C6 H6A 107.2 . . ?
C7 C6 H6B 107.2 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 111.7(4) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 C7 110.9(9) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C8 C9 H9A 107.2 . . ?
C8 C9 H9B 107.2 . . ?
C8 C9 B1 120.5(12) . . ?
H9A C9 H9B 106.8 . . ?
B1 C9 H9A 107.2 . . ?
B1 C9 H9B 107.2 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1B N1B C5B 119.0(12) . . ?
C1B N1B B1 118.2(10) . . ?
C5B N1B B1 120.5(12) . . ?
N1B C1B C2B 120.0(10) . . ?
N1B C1B C10B 120.3(13) . . ?
C2B C1B C10B 116.7(12) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B C1B 120.1(10) . . ?
C3B C2B H2B 119.9 . . ?
C2B C3B H3B 120.6 . . ?
C2B C3B C4B 118.9(10) . . ?
C4B C3B H3B 120.6 . . ?
C3B C4B H4B 119.6 . . ?
C3B C4B C5B 120.8(8) . . ?
C5B C4B H4B 119.6 . . ?
N1B C5B C4B 119.9(8) . . ?
N1B C5B C6B 124.8(8) . . ?
C4B C5B C6B 115.1(6) . . ?
C5B C6B H6BA 107.8 . . ?
C5B C6B H6BB 107.8 . . ?
C5B C6B C7B 118.0(3) . . ?
H6BA C6B H6BB 107.1 . . ?
C7B C6B H6BA 107.8 . . ?
C7B C6B H6BB 107.8 . . ?
C6B C7B H7BA 109.3 . . ?
C6B C7B H7BB 109.3 . . ?
C6B C7B C8B 111.7(5) . . ?
H7BA C7B H7BB 107.9 . . ?
C8B C7B H7BA 109.3 . . ?
C8B C7B H7BB 109.3 . . ?
C7B C8B H8BA 109.8 . . ?
C7B C8B H8BB 109.8 . . ?
C7B C8B C9B 109.5(11) . . ?
H8BA C8B H8BB 108.2 . . ?
C9B C8B H8BA 109.8 . . ?
C9B C8B H8BB 109.8 . . ?
C8B C9B H9BA 108.0 . . ?
C8B C9B H9BB 108.0 . . ?
C8B C9B B1 117.1(16) . . ?
H9BA C9B H9BB 107.3 . . ?
B1 C9B H9BA 108.0 . . ?
B1 C9B H9BB 108.0 . . ?
C1B C10B H10D 109.5 . . ?
C1B C10B H10E 109.5 . . ?
C1B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C12 C11 B1 120.12(11) . . ?
C16 C11 C12 112.93(11) . . ?
C16 C11 B1 126.81(11) . . ?
F1 C12 C11 120.11(11) . . ?
F1 C12 C13 115.39(11) . . ?
C13 C12 C11 124.45(12) . . ?
F2 C13 C12 120.49(12) . . ?
F2 C13 C14 119.85(11) . . ?
C14 C13 C12 119.65(12) . . ?
F3 C14 C13 120.76(12) . . ?
F3 C14 C15 120.54(12) . . ?
C15 C14 C13 118.70(12) . . ?
F4 C15 C14 119.89(12) . . ?
F4 C15 C16 120.53(12) . . ?
C14 C15 C16 119.58(12) . . ?
F5 C16 C11 120.70(12) . . ?
F5 C16 C15 114.56(12) . . ?
C15 C16 C11 124.67(12) . . ?
C18 C17 B1 120.05(11) . . ?
C22 C17 C18 112.90(11) . . ?
C22 C17 B1 127.00(11) . . ?
F6 C18 C17 119.80(12) . . ?
F6 C18 C19 115.41(12) . . ?
C19 C18 C17 124.77(12) . . ?
F7 C19 C18 120.92(13) . . ?
F7 C19 C20 119.70(12) . . ?
C20 C19 C18 119.38(12) . . ?
F8 C20 C19 120.35(13) . . ?
F8 C20 C21 120.78(13) . . ?
C21 C20 C19 118.85(12) . . ?
F9 C21 C20 119.93(12) . . ?
F9 C21 C22 120.25(12) . . ?
C20 C21 C22 119.81(12) . . ?
F10 C22 C17 121.12(11) . . ?
F10 C22 C21 114.60(11) . . ?
C21 C22 C17 124.28(12) . . ?
N1 B1 C9 108.7(8) . . ?
N1 B1 C11 107.7(9) . . ?
N1B B1 C11 105.3(12) . . ?
C9B B1 N1B 114.6(10) . . ?
C9B B1 C11 104.3(6) . . ?
C9B B1 C17 108.1(9) . . ?
C11 B1 C9 102.9(5) . . ?
C17 B1 N1 110.2(14) . . ?
C17 B1 C9 112.8(6) . . ?
C17 B1 N1B 110.4(17) . . ?
C17 B1 C11 114.20(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C12 C13 F2 -3.00(17) . . . . ?
F1 C12 C13 C14 176.41(11) . . . . ?
F2 C13 C14 F3 0.55(19) . . . . ?
F2 C13 C14 C15 -179.34(12) . . . . ?
F3 C14 C15 F4 -0.4(2) . . . . ?
F3 C14 C15 C16 178.87(12) . . . . ?
F4 C15 C16 F5 3.46(19) . . . . ?
F4 C15 C16 C11 -179.73(12) . . . . ?
F6 C18 C19 F7 -1.64(19) . . . . ?
F6 C18 C19 C20 178.38(12) . . . . ?
F7 C19 C20 F8 -0.61(19) . . . . ?
F7 C19 C20 C21 -179.46(12) . . . . ?
F8 C20 C21 F9 -0.27(19) . . . . ?
F8 C20 C21 C22 -179.25(12) . . . . ?
F9 C21 C22 F10 0.19(18) . . . . ?
F9 C21 C22 C17 -179.40(12) . . . . ?
N1 C1 C2 C3 14(3) . . . . ?
N1 C5 C6 C7 -82.7(18) . . . . ?
C1 N1 C5 C4 22(4) . . . . ?
C1 N1 C5 C6 -150(2) . . . . ?
C1 N1 B1 C9 -149(3) . . . . ?
C1 N1 B1 N1B -8(60) . . . . ?
C1 N1 B1 C9B -152(3) . . . . ?
C1 N1 B1 C11 -38(3) . . . . ?
C1 N1 B1 C17 87(3) . . . . ?
C1 C2 C3 C4 2.3(19) . . . . ?
C2 C3 C4 C5 -6.4(14) . . . . ?
C3 C4 C5 N1 -6(2) . . . . ?
C3 C4 C5 C6 166.3(7) . . . . ?
C4 C5 C6 C7 105.2(5) . . . . ?
C5 N1 C1 C2 -26(4) . . . . ?
C5 N1 C1 C10 165(2) . . . . ?
C5 N1 B1 C9 33(3) . . . . ?
C5 N1 B1 N1B 173(65) . . . . ?
C5 N1 B1 C9B 30(3) . . . . ?
C5 N1 B1 C11 144(2) . . . . ?
C5 N1 B1 C17 -91(3) . . . . ?
C5 C6 C7 C8 77.2(6) . . . . ?
C6 C7 C8 C9 -58.9(10) . . . . ?
C7 C8 C9 B1 77.0(14) . . . . ?
C8 C9 B1 N1 -79.8(16) . . . . ?
C8 C9 B1 N1B -82(2) . . . . ?
C8 C9 B1 C9B 59(12) . . . . ?
C8 C9 B1 C11 166.2(11) . . . . ?
C8 C9 B1 C17 42.7(14) . . . . ?
C10 C1 C2 C3 -176.1(14) . . . . ?
N1B C1B C2B C3B -13(4) . . . . ?
N1B C5B C6B C7B 29(3) . . . . ?
C1B N1B C5B C4B -2(5) . . . . ?
C1B N1B C5B C6B -178(3) . . . . ?
C1B N1B B1 N1 173(66) . . . . ?
C1B N1B B1 C9 -146(3) . . . . ?
C1B N1B B1 C9B -150(3) . . . . ?
C1B N1B B1 C11 -36(4) . . . . ?
C1B N1B B1 C17 88(4) . . . . ?
C1B C2B C3B C4B 11(3) . . . . ?
C2B C3B C4B C5B -5.4(19) . . . . ?
C3B C4B C5B N1B 1(3) . . . . ?
C3B C4B C5B C6B 176.5(10) . . . . ?
C4B C5B C6B C7B -146.5(5) . . . . ?
C5B N1B C1B C2B 8(6) . . . . ?
C5B N1B C1B C10B 168(3) . . . . ?
C5B N1B B1 N1 -24(59) . . . . ?
C5B N1B B1 C9 17(4) . . . . ?
C5B N1B B1 C9B 13(4) . . . . ?
C5B N1B B1 C11 127(3) . . . . ?
C5B N1B B1 C17 -109(3) . . . . ?
C5B C6B C7B C8B -89.1(7) . . . . ?
C6B C7B C8B C9B 41.9(13) . . . . ?
C7B C8B C9B B1 48.4(19) . . . . ?
C8B C9B B1 N1 -77(2) . . . . ?
C8B C9B B1 C9 -120(14) . . . . ?
C8B C9B B1 N1B -79(2) . . . . ?
C8B C9B B1 C11 166.8(14) . . . . ?
C8B C9B B1 C17 44.9(18) . . . . ?
C10B C1B C2B C3B -173.6(17) . . . . ?
C11 C12 C13 F2 179.59(11) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C11 C16 F5 175.96(11) . . . . ?
C12 C11 C16 C15 -0.66(19) . . . . ?
C12 C11 B1 N1 -59.3(11) . . . . ?
C12 C11 B1 C9 55.4(7) . . . . ?
C12 C11 B1 N1B -60.7(14) . . . . ?
C12 C11 B1 C9B 60.2(10) . . . . ?
C12 C11 B1 C17 177.99(11) . . . . ?
C12 C13 C14 F3 -178.87(12) . . . . ?
C12 C13 C14 C15 1.24(19) . . . . ?
C13 C14 C15 F4 179.49(12) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C14 C15 C16 F5 -175.80(12) . . . . ?
C14 C15 C16 C11 1.0(2) . . . . ?
C16 C11 C12 F1 -176.64(11) . . . . ?
C16 C11 C12 C13 0.66(18) . . . . ?
C16 C11 B1 N1 125.3(11) . . . . ?
C16 C11 B1 C9 -120.0(7) . . . . ?
C16 C11 B1 N1B 123.9(14) . . . . ?
C16 C11 B1 C9B -115.2(10) . . . . ?
C16 C11 B1 C17 2.62(18) . . . . ?
C17 C18 C19 F7 -179.84(12) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C17 C22 F10 -178.53(11) . . . . ?
C18 C17 C22 C21 1.04(19) . . . . ?
C18 C17 B1 N1 173.5(4) . . . . ?
C18 C17 B1 C9 51.9(6) . . . . ?
C18 C17 B1 N1B 176.5(5) . . . . ?
C18 C17 B1 C9B 50.4(7) . . . . ?
C18 C17 B1 C11 -65.17(15) . . . . ?
C18 C19 C20 F8 179.38(12) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 F9 178.57(12) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 F10 179.16(11) . . . . ?
C20 C21 C22 C17 -0.4(2) . . . . ?
C22 C17 C18 F6 -179.05(11) . . . . ?
C22 C17 C18 C19 -0.91(19) . . . . ?
C22 C17 B1 N1 -3.7(4) . . . . ?
C22 C17 B1 C9 -125.3(6) . . . . ?
C22 C17 B1 N1B -0.7(5) . . . . ?
C22 C17 B1 C9B -126.8(7) . . . . ?
C22 C17 B1 C11 117.64(14) . . . . ?
B1 N1 C1 C2 156(2) . . . . ?
B1 N1 C1 C10 -13(4) . . . . ?
B1 N1 C5 C4 -160.0(17) . . . . ?
B1 N1 C5 C6 28(3) . . . . ?
B1 N1B C1B C2B 172(3) . . . . ?
B1 N1B C1B C10B -29(5) . . . . ?
B1 N1B C5B C4B -165(2) . . . . ?
B1 N1B C5B C6B 20(5) . . . . ?
B1 C11 C12 F1 7.39(17) . . . . ?
B1 C11 C12 C13 -175.31(12) . . . . ?
B1 C11 C16 F5 -8.4(2) . . . . ?
B1 C11 C16 C15 174.99(12) . . . . ?
B1 C17 C18 F6 3.39(18) . . . . ?
B1 C17 C18 C19 -178.48(12) . . . . ?
B1 C17 C22 F10 -1.17(19) . . . . ?
B1 C17 C22 C21 178.40(12) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-13 1 12 0.0156 -13.0048 0.9970 11.9543 0.1916 -0.9734 -0.1410
8 -14 8 0.1085 7.6346 -13.5490 8.4562 0.4380 0.0799 0.8954
10 9 10 0.1264 9.5943 9.4562 9.9851 -0.7199 -0.1352 0.6808
13 -1 -12 0.0156 13.0048 -0.9970 -11.9543 -0.1916 0.9734 0.1410
-8 13 -9 0.1100 -7.9389 12.9825 -8.7664 -0.4023 -0.0733 -0.9125
-11 -1 -12 0.1166 -10.8746 -0.7864 -11.5582 0.3396 0.0649 -0.9383
-4 -18 -3 0.1065 -3.6040 -18.4105 -3.3908 0.9831 0.1830 -0.0064
1 19 1 0.1086 1.3555 19.2784 0.9759 -0.9623 -0.1788 -0.2049

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-2

