# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mjh120018

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 B Br F2 N2'
_chemical_formula_sum            'C22 H24 B Br F2 N2'
_chemical_formula_weight         445.15

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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                   11.2831(3)
_cell_length_b                   11.2485(2)
_cell_length_c                   15.7815(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.037(2)
_cell_angle_gamma                90.00
_cell_volume                     2001.69(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.8306
_cell_measurement_theta_max      28.5236

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    2.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_T_max  0.8189
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'thick-slice ω scans'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_reflns_number            18680
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         28.59
_reflns_number_total             4484
_reflns_number_gt                3971
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
'Tue Aug 07 22:31:57 2012'
;
_computing_cell_refinement       
;
'Tue Aug 07 22:31:57 2012'
;
_computing_data_reduction        
;
'Tue Aug 07 22:31:57 2012'
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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)+(0.0447P)²+2.3261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4484
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Br Br 0.36867(2) -0.32782(2) 0.665293(17) 0.03235(10) Uani 1 1 d . . .
N1 N -0.03487(16) 0.07882(16) 0.61606(11) 0.0178(4) Uani 1 1 d . . .
N2 N 0.10469(17) -0.08805(16) 0.64241(11) 0.0182(4) Uani 1 1 d . . .
F1 F -0.09534(12) -0.12422(12) 0.59190(9) 0.0289(3) Uani 1 1 d . . .
F2 F -0.06604(13) -0.06252(12) 0.72754(8) 0.0269(3) Uani 1 1 d . . .
B B -0.0268(2) -0.0519(2) 0.64534(16) 0.0192(5) Uani 1 1 d . . .
C1 C -0.1341(2) 0.1417(2) 0.60088(14) 0.0197(4) Uani 1 1 d . . .
C2 C -0.1052(2) 0.2605(2) 0.58024(14) 0.0200(4) Uani 1 1 d . . .
C3 C 0.0173(2) 0.26999(19) 0.58556(13) 0.0188(4) Uani 1 1 d . . .
C4 C 0.0626(2) 0.15429(19) 0.60704(13) 0.0177(4) Uani 1 1 d . . .
C5 C 0.17681(19) 0.11105(19) 0.61428(13) 0.0171(4) Uani 1 1 d . . .
C6 C 0.19887(19) -0.01094(19) 0.63016(13) 0.0180(4) Uani 1 1 d . . .
C7 C 0.3061(2) -0.0771(2) 0.63500(14) 0.0205(5) Uani 1 1 d . . .
C8 C 0.2702(2) -0.1936(2) 0.65043(15) 0.0226(5) Uani 1 1 d . . .
C9 C 0.1471(2) -0.19907(19) 0.65528(14) 0.0214(5) Uani 1 1 d . . .
C10 C -0.2551(2) 0.0904(2) 0.60609(17) 0.0271(5) Uani 1 1 d . . .
H10A H -0.2531 0.0237 0.6461 0.041 Uiso 1 1 calc R . .
H10B H -0.2821 0.0621 0.5499 0.041 Uiso 1 1 calc R . .
H10C H -0.3097 0.1514 0.6257 0.041 Uiso 1 1 calc R . .
C11 C -0.1934(2) 0.3571(2) 0.55783(15) 0.0248(5) Uani 1 1 d . . .
H11A H -0.1631 0.4045 0.5104 0.030 Uiso 1 1 calc R . .
H11B H -0.2689 0.3199 0.5380 0.030 Uiso 1 1 calc R . .
C12 C -0.2167(2) 0.4362(2) 0.62808(16) 0.0277(5) Uani 1 1 d . . .
H12A H -0.2668 0.5022 0.6079 0.042 Uiso 1 1 calc R . .
H12B H -0.1415 0.4676 0.6517 0.042 Uiso 1 1 calc R . .
H12C H -0.2574 0.3922 0.6721 0.042 Uiso 1 1 calc R . .
C13 C 0.0859(2) 0.3810(2) 0.56940(16) 0.0239(5) Uani 1 1 d . . .
H13A H 0.0315 0.4489 0.5657 0.036 Uiso 1 1 calc R . .
H13B H 0.1269 0.3731 0.5160 0.036 Uiso 1 1 calc R . .
H13C H 0.1443 0.3939 0.6160 0.036 Uiso 1 1 calc R . .
C14 C 0.4307(2) -0.0354(2) 0.62525(17) 0.0289(5) Uani 1 1 d . . .
H14A H 0.4842 -0.1040 0.6257 0.043 Uiso 1 1 calc R . .
H14B H 0.4532 0.0179 0.6722 0.043 Uiso 1 1 calc R . .
H14C H 0.4363 0.0073 0.5714 0.043 Uiso 1 1 calc R . .
C15 C 0.0702(2) -0.3029(2) 0.67228(17) 0.0280(5) Uani 1 1 d . . .
H15A H 0.0194 -0.2845 0.7196 0.042 Uiso 1 1 calc R . .
H15B H 0.1197 -0.3720 0.6868 0.042 Uiso 1 1 calc R . .
H15C H 0.0206 -0.3206 0.6216 0.042 Uiso 1 1 calc R . .
C16 C 0.2788(2) 0.19399(19) 0.60262(15) 0.0201(4) Uani 1 1 d . . .
C17 C 0.3156(2) 0.2171(2) 0.52012(16) 0.0260(5) Uani 1 1 d . . .
H17A H 0.2777 0.1781 0.4732 0.031 Uiso 1 1 calc R . .
C18 C 0.4062(2) 0.2960(2) 0.50709(17) 0.0312(6) Uani 1 1 d . . .
H18A H 0.4308 0.3117 0.4512 0.037 Uiso 1 1 calc R . .
C19 C 0.4616(2) 0.3526(2) 0.57586(18) 0.0310(6) Uani 1 1 d . . .
H19A H 0.5242 0.4073 0.5670 0.037 Uiso 1 1 calc R . .
C20 C 0.4265(2) 0.3302(2) 0.65659(17) 0.0289(5) Uani 1 1 d . . .
H20A H 0.4655 0.3693 0.7031 0.035 Uiso 1 1 calc R . .
C21 C 0.3338(2) 0.2503(2) 0.67184(15) 0.0232(5) Uani 1 1 d . . .
C22 C 0.2944(2) 0.2295(2) 0.76007(16) 0.0312(6) Uani 1 1 d . . .
H22A H 0.3004 0.1446 0.7735 0.047 Uiso 1 1 calc R . .
H22B H 0.2119 0.2554 0.7644 0.047 Uiso 1 1 calc R . .
H22C H 0.3449 0.2749 0.8001 0.047 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
Br C8 1.884(2) . ?
N1 B 1.543(3) . ?
N1 C1 1.339(3) . ?
N1 C4 1.401(3) . ?
N2 B 1.541(3) . ?
N2 C6 1.391(3) . ?
N2 C9 1.350(3) . ?
F1 B 1.388(3) . ?
F2 B 1.391(3) . ?
C1 C2 1.416(3) . ?
C1 C10 1.487(3) . ?
C2 C3 1.386(3) . ?
C2 C11 1.507(3) . ?
C3 C4 1.434(3) . ?
C3 C13 1.496(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.415(3) . ?
C5 C16 1.498(3) . ?
C6 C7 1.420(3) . ?
C7 C8 1.395(3) . ?
C7 C14 1.496(3) . ?
C8 C9 1.395(3) . ?
C9 C15 1.485(3) . ?
C10 H10A 0.980 . ?
C10 H10B 0.980 . ?
C10 H10C 0.980 . ?
C11 H11A 0.990 . ?
C11 H11B 0.990 . ?
C11 C12 1.453(4) . ?
C12 H12A 0.980 . ?
C12 H12B 0.980 . ?
C12 H12C 0.980 . ?
C13 H13A 0.980 . ?
C13 H13B 0.980 . ?
C13 H13C 0.980 . ?
C14 H14A 0.980 . ?
C14 H14B 0.980 . ?
C14 H14C 0.980 . ?
C15 H15A 0.980 . ?
C15 H15B 0.980 . ?
C15 H15C 0.980 . ?
C16 C17 1.405(3) . ?
C16 C21 1.390(3) . ?
C17 H17A 0.950 . ?
C17 C18 1.375(3) . ?
C18 H18A 0.950 . ?
C18 C19 1.388(4) . ?
C19 H19A 0.950 . ?
C19 C20 1.371(4) . ?
C20 H20A 0.950 . ?
C20 C21 1.406(3) . ?
C21 C22 1.495(3) . ?
C22 H22A 0.980 . ?
C22 H22B 0.980 . ?
C22 H22C 0.980 . ?

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
B N1 C1 126.68(19) . . ?
B N1 C4 124.74(19) . . ?
C1 N1 C4 108.42(18) . . ?
B N2 C6 125.51(18) . . ?
B N2 C9 125.21(19) . . ?
C6 N2 C9 109.22(19) . . ?
N1 B N2 106.82(18) . . ?
N1 B F1 110.56(19) . . ?
N1 B F2 110.13(18) . . ?
N2 B F1 110.08(18) . . ?
N2 B F2 110.12(19) . . ?
F1 B F2 109.11(19) . . ?
N1 C1 C2 110.0(2) . . ?
N1 C1 C10 123.2(2) . . ?
C2 C1 C10 126.8(2) . . ?
C1 C2 C3 107.2(2) . . ?
C1 C2 C11 125.3(2) . . ?
C3 C2 C11 127.4(2) . . ?
C2 C3 C4 106.88(19) . . ?
C2 C3 C13 125.1(2) . . ?
C4 C3 C13 128.0(2) . . ?
N1 C4 C3 107.44(19) . . ?
N1 C4 C5 120.86(19) . . ?
C3 C4 C5 131.6(2) . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 C16 119.36(19) . . ?
C6 C5 C16 119.63(19) . . ?
N2 C6 C5 119.9(2) . . ?
N2 C6 C7 108.61(19) . . ?
C5 C6 C7 131.5(2) . . ?
C6 C7 C8 104.5(2) . . ?
C6 C7 C14 129.2(2) . . ?
C8 C7 C14 126.3(2) . . ?
Br C8 C7 126.96(18) . . ?
Br C8 C9 122.78(17) . . ?
C7 C8 C9 110.2(2) . . ?
N2 C9 C8 107.4(2) . . ?
N2 C9 C15 123.2(2) . . ?
C8 C9 C15 129.4(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 . . ?
C2 C11 H11A 108.9 . . ?
C2 C11 H11B 108.9 . . ?
C2 C11 C12 113.5(2) . . ?
H11A C11 H11B 107.7 . . ?
H11A C11 C12 108.9 . . ?
H11B C11 C12 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 C17 118.9(2) . . ?
C5 C16 C21 120.7(2) . . ?
C17 C16 C21 120.4(2) . . ?
C16 C17 H17A 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
H17A C17 C18 119.9 . . ?
C17 C18 H18A 120.1 . . ?
C17 C18 C19 119.7(2) . . ?
H18A C18 C19 120.1 . . ?
C18 C19 H19A 119.8 . . ?
C18 C19 C20 120.3(2) . . ?
H19A C19 C20 119.8 . . ?
C19 C20 H20A 119.4 . . ?
C19 C20 C21 121.2(2) . . ?
H20A C20 C21 119.4 . . ?
C16 C21 C20 118.1(2) . . ?
C16 C21 C22 121.4(2) . . ?
C20 C21 C22 120.5(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C6 N2 B N1 10.2(3) . . . . ?
C6 N2 B F1 130.3(2) . . . . ?
C6 N2 B F2 -109.4(2) . . . . ?
C9 N2 B N1 -173.06(19) . . . . ?
C9 N2 B F1 -53.0(3) . . . . ?
C9 N2 B F2 67.4(3) . . . . ?
C1 N1 B N2 172.67(19) . . . . ?
C1 N1 B F1 52.9(3) . . . . ?
C1 N1 B F2 -67.7(3) . . . . ?
C4 N1 B N2 -12.4(3) . . . . ?
C4 N1 B F1 -132.2(2) . . . . ?
C4 N1 B F2 107.2(2) . . . . ?
B N1 C1 C2 176.39(19) . . . . ?
B N1 C1 C10 -3.4(3) . . . . ?
C4 N1 C1 C2 0.8(2) . . . . ?
C4 N1 C1 C10 -179.0(2) . . . . ?
N1 C1 C2 C3 -1.7(3) . . . . ?
N1 C1 C2 C11 178.9(2) . . . . ?
C10 C1 C2 C3 178.1(2) . . . . ?
C10 C1 C2 C11 -1.3(4) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C1 C2 C3 C13 -179.5(2) . . . . ?
C11 C2 C3 C4 -178.8(2) . . . . ?
C11 C2 C3 C13 -0.1(4) . . . . ?
B N1 C4 C3 -175.34(19) . . . . ?
B N1 C4 C5 8.1(3) . . . . ?
C1 N1 C4 C3 0.4(2) . . . . ?
C1 N1 C4 C5 -176.2(2) . . . . ?
C2 C3 C4 N1 -1.4(2) . . . . ?
C2 C3 C4 C5 174.7(2) . . . . ?
C13 C3 C4 N1 180.0(2) . . . . ?
C13 C3 C4 C5 -4.0(4) . . . . ?
N1 C4 C5 C6 0.6(3) . . . . ?
N1 C4 C5 C16 178.86(19) . . . . ?
C3 C4 C5 C6 -175.0(2) . . . . ?
C3 C4 C5 C16 3.2(4) . . . . ?
B N2 C6 C5 -3.6(3) . . . . ?
B N2 C6 C7 177.61(19) . . . . ?
C9 N2 C6 C5 179.21(19) . . . . ?
C9 N2 C6 C7 0.4(2) . . . . ?
C4 C5 C6 N2 -2.8(3) . . . . ?
C4 C5 C6 C7 175.6(2) . . . . ?
C16 C5 C6 N2 178.95(19) . . . . ?
C16 C5 C6 C7 -2.6(3) . . . . ?
N2 C6 C7 C8 -0.1(2) . . . . ?
N2 C6 C7 C14 179.3(2) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C5 C6 C7 C14 0.7(4) . . . . ?
C6 C7 C8 Br -179.19(17) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C14 C7 C8 Br 1.4(4) . . . . ?
C14 C7 C8 C9 -179.7(2) . . . . ?
B N2 C9 C8 -177.8(2) . . . . ?
B N2 C9 C15 1.5(3) . . . . ?
C6 N2 C9 C8 -0.6(2) . . . . ?
C6 N2 C9 C15 178.7(2) . . . . ?
Br C8 C9 N2 179.50(16) . . . . ?
Br C8 C9 C15 0.3(4) . . . . ?
C7 C8 C9 N2 0.5(3) . . . . ?
C7 C8 C9 C15 -178.7(2) . . . . ?
C1 C2 C11 C12 99.4(3) . . . . ?
C3 C2 C11 C12 -79.8(3) . . . . ?
C4 C5 C16 C17 -84.5(3) . . . . ?
C4 C5 C16 C21 93.3(3) . . . . ?
C6 C5 C16 C17 93.7(3) . . . . ?
C6 C5 C16 C21 -88.4(3) . . . . ?
C5 C16 C17 C18 177.7(2) . . . . ?
C21 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C5 C16 C21 C20 -177.9(2) . . . . ?
C5 C16 C21 C22 0.6(3) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
C17 C16 C21 C22 178.5(2) . . . . ?
C19 C20 C21 C16 0.3(4) . . . . ?
C19 C20 C21 C22 -178.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.877
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 984417'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mjh120032
_audit_creation_date             2014-01-24
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.01.21 svn.r2874 for OlexSys, GUI svn.r4743)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H31 B F2 N2 O2'
_chemical_formula_sum            'C27 H31 B F2 N2 O2'
_chemical_formula_weight         464.35
_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 0.0030 0.0010 '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 0.0010 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 '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                   7.712(5)
_cell_length_b                   25.125(15)
_cell_length_c                   12.348(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.318(7)
_cell_angle_gamma                90
_cell_volume                     2391(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    150
_cell_measurement_theta_max      22.09
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1490 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8783.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_Laue_measured_fraction_full 0.670
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10761
_diffrn_reflns_point_group_measured_fraction_full 0.670
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         21.257
_diffrn_reflns_theta_min         1.782
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.670
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_special_details          
'Size and quality of crystal limited resolution attainable'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1819
_reflns_number_total             2897
_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       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     320
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.007
_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)+(0.0877P)²+0.4420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1715
_refine_special_details          
;
Minor disorder was present in the molecule, fractional occupancies were 
refined and then fixed for these atoms to allow anisotropic refinement.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2A-C18 \\sim O2-C18
 with sigma of 0.02
 O2A-C19A \\sim O2-C19
 with sigma of 0.02
 C20-C19 \\sim C20A-C19A
 with sigma of 0.02
 C20A-O2A \\sim C20-O2
 with sigma of 0.02
 O1-C18 \\sim O1A-C18
 with sigma of 0.02
 O2A-O1 \\sim O1A-O2
 with sigma of 0.02
3. Restrained planarity
 C22, C23, C24, C25, C26, C21
 with sigma of 0.1
 O1, C18, O2, C17
 with sigma of 0.1
 O2A, C18, O1A, C17
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(O1) = Uanis(O1A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O1(0.8) O2(0.8) C19(0.8) H19A(0.8) H19B(0.8) C20(0.8) H20A(0.8)
 H20B(0.8) H20C(0.8) O2A(0.2) C19A(0.2) H19C(0.2) H19D(0.2) C20A(0.2) H20D(0.2)
 H20E(0.2) H20F(0.2) O1A(0.2)
7.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B), C19A(H19C,H19D)
7.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C22(H22), C23(H23), C24(H24), C25(H25)
7.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F),
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
B B 0.3579(7) 0.38896(17) 0.4196(4) 0.0553(12) Uani 1 1 d . . . . .
O1 O 1.1559(12) 0.5155(2) 0.1265(4) 0.0815(19) Uani 0.8 1 d . . P A 1
O2 O 1.2493(5) 0.52521(14) 0.2978(3) 0.0673(10) Uani 0.8 1 d . . P A 1
N1 N 0.1956(4) 0.36165(12) 0.3683(3) 0.0540(9) Uani 1 1 d . . . . .
N2 N 0.4739(4) 0.40521(11) 0.3264(3) 0.0535(9) Uani 1 1 d . . . . .
F1 F 0.4459(3) 0.35417(8) 0.48898(18) 0.0660(7) Uani 1 1 d . . . . .
F2 F 0.3088(3) 0.43307(9) 0.47764(19) 0.0773(8) Uani 1 1 d . . . . .
C1 C 0.0590(5) 0.34273(15) 0.4206(3) 0.0581(11) Uani 1 1 d . . . . .
C2 C -0.0628(5) 0.32050(16) 0.3461(4) 0.0606(11) Uani 1 1 d . . . . .
C3 C 0.0034(5) 0.32597(16) 0.2439(3) 0.0577(11) Uani 1 1 d . . . . .
C4 C 0.1664(5) 0.35193(14) 0.2571(3) 0.0541(10) Uani 1 1 d . . . . .
C5 C 0.2868(5) 0.36769(14) 0.1837(3) 0.0498(10) Uani 1 1 d . . . . .
C6 C 0.4381(5) 0.39471(14) 0.2155(3) 0.0506(10) Uani 1 1 d . . . . .
C7 C 0.5765(5) 0.41516(14) 0.1573(3) 0.0552(10) Uani 1 1 d . . . . .
C8 C 0.6952(5) 0.43789(14) 0.2324(3) 0.0555(10) Uani 1 1 d . . . . .
C9 C 0.6277(5) 0.43088(14) 0.3361(3) 0.0544(10) Uani 1 1 d . . . . .
C10 C 0.0507(6) 0.34582(18) 0.5402(3) 0.0720(13) Uani 1 1 d . . . . .
H10A H 0.1465 0.3253 0.5740 0.108 Uiso 1 1 calc GR . . . .
H10B H -0.0600 0.3311 0.5625 0.108 Uiso 1 1 calc GR . . . .
H10C H 0.0600 0.3831 0.5633 0.108 Uiso 1 1 calc GR . . . .
C11 C -0.2328(5) 0.29584(18) 0.3731(4) 0.0722(13) Uani 1 1 d . . . . .
H11A H -0.2598 0.3058 0.4481 0.087 Uiso 1 1 calc R . . . .
H11B H -0.3251 0.3107 0.3240 0.087 Uiso 1 1 calc R . . . .
C12 C -0.2356(6) 0.23679(18) 0.3638(4) 0.0807(14) Uani 1 1 d . . . . .
H12A H -0.2111 0.2265 0.2894 0.121 Uiso 1 1 calc GR . . . .
H12B H -0.3504 0.2235 0.3818 0.121 Uiso 1 1 calc GR . . . .
H12C H -0.1474 0.2215 0.4140 0.121 Uiso 1 1 calc GR . . . .
C13 C -0.0867(5) 0.30902(18) 0.1415(4) 0.0690(12) Uani 1 1 d . . . . .
H13A H -0.0225 0.2797 0.1094 0.104 Uiso 1 1 calc GR . . . .
H13B H -0.0930 0.3390 0.0908 0.104 Uiso 1 1 calc GR . . . .
H13C H -0.2044 0.2971 0.1564 0.104 Uiso 1 1 calc GR . . . .
C14 C 0.5949(6) 0.41427(18) 0.0371(3) 0.0703(13) Uani 1 1 d . . . . .
H14A H 0.5825 0.3776 0.0106 0.105 Uiso 1 1 calc GR . . . .
H14B H 0.7095 0.4280 0.0198 0.105 Uiso 1 1 calc GR . . . .
H14C H 0.5047 0.4366 0.0022 0.105 Uiso 1 1 calc GR . . . .
C15 C 0.7058(6) 0.44592(16) 0.4431(3) 0.0673(12) Uani 1 1 d . . . . .
H15A H 0.7142 0.4848 0.4480 0.101 Uiso 1 1 calc GR . . . .
H15B H 0.8221 0.4304 0.4518 0.101 Uiso 1 1 calc GR . . . .
H15C H 0.6330 0.4326 0.5004 0.101 Uiso 1 1 calc GR . . . .
C16 C 0.8558(6) 0.46413(15) 0.2059(3) 0.0590(11) Uani 1 1 d . . . . .
H16 H 0.8740 0.4669 0.1305 0.071 Uiso 1 1 calc R . . . .
C17 C 0.9784(6) 0.48438(18) 0.2678(4) 0.0780(13) Uani 1 1 d . . . . .
H17 H 0.9703 0.4829 0.3443 0.094 Uiso 1 1 calc R . . . .
C18 C 1.1287(6) 0.50947(17) 0.2212(4) 0.0750(13) Uani 1 1 d . . . . .
C19 C 1.4007(7) 0.5517(2) 0.2628(5) 0.0660(16) Uani 0.8 1 d . . P A 1
H19A H 1.4343 0.5366 0.1927 0.079 Uiso 0.8 1 calc R . P A 1
H19B H 1.4977 0.5457 0.3164 0.079 Uiso 0.8 1 calc R . P A 1
C20 C 1.3703(7) 0.6108(2) 0.2499(5) 0.0706(16) Uani 0.8 1 d . . P A 1
H20A H 1.2817 0.6170 0.1922 0.106 Uiso 0.8 1 calc GR . P A 1
H20B H 1.4788 0.6282 0.2311 0.106 Uiso 0.8 1 calc GR . P A 1
H20C H 1.3308 0.6255 0.3182 0.106 Uiso 0.8 1 calc GR . P A 1
C21 C 0.2575(5) 0.35277(15) 0.0675(3) 0.0548(10) Uani 1 1 d . . . . .
C22 C 0.1782(5) 0.38839(18) -0.0046(4) 0.0661(12) Uani 1 1 d . . . . .
H22 H 0.1446 0.4227 0.0195 0.079 Uiso 1 1 calc R . . . .
C23 C 0.1484(6) 0.3738(2) -0.1112(4) 0.0816(14) Uani 1 1 d . . . . .
H23 H 0.0942 0.3982 -0.1607 0.098 Uiso 1 1 calc R . . . .
C24 C 0.1963(6) 0.3244(2) -0.1465(4) 0.0785(14) Uani 1 1 d . . . . .
H24 H 0.1737 0.3146 -0.2200 0.094 Uiso 1 1 calc R . . . .
C25 C 0.2768(5) 0.28880(19) -0.0761(4) 0.0690(12) Uani 1 1 d . . . . .
H25 H 0.3110 0.2549 -0.1016 0.083 Uiso 1 1 calc R . . . .
C26 C 0.3086(5) 0.30245(16) 0.0327(3) 0.0561(11) Uani 1 1 d . . . . .
O2A O 1.1729(17) 0.5540(5) 0.2952(11) 0.0673(10) Uani 0.2 1 d . . P A 2
C19A C 1.315(2) 0.5899(8) 0.265(2) 0.0660(16) Uani 0.2 1 d . . P A 2
H19C H 1.3307 0.6188 0.3185 0.079 Uiso 0.2 1 calc R . P A 2
H19D H 1.2885 0.6060 0.1927 0.079 Uiso 0.2 1 calc R . P A 2
C20A C 1.478(2) 0.5569(11) 0.261(2) 0.0706(16) Uani 0.2 1 d . . P A 2
H20D H 1.4639 0.5297 0.2049 0.106 Uiso 0.2 1 calc GR . P A 2
H20E H 1.5003 0.5397 0.3318 0.106 Uiso 0.2 1 calc GR . P A 2
H20F H 1.5764 0.5800 0.2452 0.106 Uiso 0.2 1 calc GR . P A 2
O1A O 1.162(5) 0.5004(14) 0.1289(12) 0.0815(19) Uani 0.2 1 d . . P A 2
C27 C 0.3957(6) 0.26506(17) 0.1081(4) 0.0760(13) Uani 1 1 d . . . . .
H27A H 0.4977 0.2823 0.1427 0.114 Uiso 1 1 calc GR . . . .
H27B H 0.4323 0.2335 0.0682 0.114 Uiso 1 1 calc GR . . . .
H27C H 0.3154 0.2544 0.1637 0.114 Uiso 1 1 calc GR . . . .


_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
B N1 1.541(6) . ?
B N2 1.541(6) . ?
B F1 1.383(5) . ?
B F2 1.381(5) . ?
O1 C18 1.206(6) . ?
O2 C18 1.358(5) . ?
O2 C19 1.427(6) . ?
N1 C1 1.345(5) . ?
N1 C4 1.404(5) . ?
N2 C6 1.411(5) . ?
N2 C9 1.351(5) . ?
C1 C2 1.404(6) . ?
C1 C10 1.483(6) . ?
C2 C3 1.387(5) . ?
C2 C11 1.499(6) . ?
C3 C4 1.420(6) . ?
C3 C13 1.481(6) . ?
C4 C5 1.381(5) . ?
C5 C6 1.393(5) . ?
C5 C21 1.492(5) . ?
C6 C7 1.408(5) . ?
C7 C8 1.398(5) . ?
C7 C14 1.497(6) . ?
C8 C9 1.414(5) . ?
C8 C16 1.452(6) . ?
C9 C15 1.479(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.488(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.296(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.458(7) . ?
C18 O2A 1.475(13) . ?
C18 O1A 1.201(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.509(7) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.387(6) . ?
C21 C26 1.397(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.372(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.398(6) . ?
C26 C27 1.466(6) . ?
O2A C19A 1.483(17) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.505(18) . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
N2 B N1 107.3(3) . . ?
F1 B N1 110.1(3) . . ?
F1 B N2 110.2(4) . . ?
F2 B N1 109.6(4) . . ?
F2 B N2 110.8(3) . . ?
F2 B F1 108.9(4) . . ?
C18 O2 C19 118.1(4) . . ?
C1 N1 B 126.8(4) . . ?
C1 N1 C4 108.1(3) . . ?
C4 N1 B 125.1(3) . . ?
C6 N2 B 125.4(3) . . ?
C9 N2 B 126.5(3) . . ?
C9 N2 C6 108.2(3) . . ?
N1 C1 C2 110.0(4) . . ?
N1 C1 C10 121.8(4) . . ?
C2 C1 C10 128.2(4) . . ?
C1 C2 C11 125.9(4) . . ?
C3 C2 C1 107.2(4) . . ?
C3 C2 C11 126.9(4) . . ?
C2 C3 C4 107.3(4) . . ?
C2 C3 C13 124.8(4) . . ?
C4 C3 C13 127.8(4) . . ?
N1 C4 C3 107.3(3) . . ?
C5 C4 N1 120.5(4) . . ?
C5 C4 C3 132.2(4) . . ?
C4 C5 C6 122.2(4) . . ?
C4 C5 C21 118.7(3) . . ?
C6 C5 C21 119.1(3) . . ?
C5 C6 N2 119.6(3) . . ?
C5 C6 C7 132.7(4) . . ?
C7 C6 N2 107.7(3) . . ?
C6 C7 C14 127.2(4) . . ?
C8 C7 C6 107.5(4) . . ?
C8 C7 C14 125.3(4) . . ?
C7 C8 C9 107.1(4) . . ?
C7 C8 C16 125.3(4) . . ?
C9 C8 C16 127.5(4) . . ?
N2 C9 C8 109.5(3) . . ?
N2 C9 C15 121.7(4) . . ?
C8 C9 C15 128.8(4) . . ?
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 . . ?
C2 C11 H11A 108.8 . . ?
C2 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C2 113.9(4) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16 114.5 . . ?
C17 C16 C8 130.9(4) . . ?
C17 C16 H16 114.5 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(5) . . ?
C18 C17 H17 119.6 . . ?
O1 C18 O2 119.8(6) . . ?
O1 C18 C17 127.5(6) . . ?
O2 C18 C17 112.6(4) . . ?
C17 C18 O2A 104.5(6) . . ?
O1A C18 C17 119.8(19) . . ?
O1A C18 O2A 133(2) . . ?
O2 C19 H19A 109.3 . . ?
O2 C19 H19B 109.3 . . ?
O2 C19 C20 111.4(4) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C5 120.1(4) . . ?
C22 C21 C26 120.6(4) . . ?
C26 C21 C5 119.3(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(5) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.5(5) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.5(5) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.3(5) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 118.5(4) . . ?
C21 C26 C27 120.8(4) . . ?
C25 C26 C27 120.7(4) . . ?
C18 O2A C19A 117.3(14) . . ?
O2A C19A H19C 110.2 . . ?
O2A C19A H19D 110.2 . . ?
O2A C19A C20A 107.5(14) . . ?
H19C C19A H19D 108.5 . . ?
C20A C19A H19C 110.2 . . ?
C20A C19A H19D 110.2 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
B N1 C1 C2 -179.8(3) . . . . ?
B N1 C1 C10 -0.7(6) . . . . ?
B N1 C4 C3 179.7(3) . . . . ?
B N1 C4 C5 -0.8(5) . . . . ?
B N2 C6 C5 0.2(5) . . . . ?
B N2 C6 C7 -179.0(3) . . . . ?
B N2 C9 C8 179.1(3) . . . . ?
B N2 C9 C15 1.2(6) . . . . ?
O1 C18 O2A C19A -28.3(17) . . . . ?
O2 C18 O2A C19A 76.0(14) . . . . ?
N1 B N2 C6 -2.2(5) . . . . ?
N1 B N2 C9 179.1(3) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
N1 C1 C2 C11 -179.4(4) . . . . ?
N1 C4 C5 C6 -1.6(5) . . . . ?
N1 C4 C5 C21 175.2(3) . . . . ?
N2 B N1 C1 -178.0(3) . . . . ?
N2 B N1 C4 2.5(5) . . . . ?
N2 C6 C7 C8 0.0(4) . . . . ?
N2 C6 C7 C14 -178.9(4) . . . . ?
F1 B N1 C1 62.0(5) . . . . ?
F1 B N1 C4 -117.4(4) . . . . ?
F1 B N2 C6 117.7(4) . . . . ?
F1 B N2 C9 -61.1(5) . . . . ?
F2 B N1 C1 -57.7(5) . . . . ?
F2 B N1 C4 122.8(4) . . . . ?
F2 B N2 C6 -121.8(4) . . . . ?
F2 B N2 C9 59.5(5) . . . . ?
C1 N1 C4 C3 0.1(4) . . . . ?
C1 N1 C4 C5 179.6(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C13 -178.2(4) . . . . ?
C1 C2 C11 C12 -107.0(5) . . . . ?
C2 C3 C4 N1 0.1(4) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
C3 C2 C11 C12 73.3(6) . . . . ?
C3 C4 C5 C6 177.7(4) . . . . ?
C3 C4 C5 C21 -5.5(6) . . . . ?
C4 N1 C1 C2 -0.2(4) . . . . ?
C4 N1 C1 C10 178.8(3) . . . . ?
C4 C5 C6 N2 1.9(5) . . . . ?
C4 C5 C6 C7 -179.0(4) . . . . ?
C4 C5 C21 C22 95.7(4) . . . . ?
C4 C5 C21 C26 -83.5(5) . . . . ?
C5 C6 C7 C8 -179.1(4) . . . . ?
C5 C6 C7 C14 2.0(7) . . . . ?
C5 C21 C22 C23 -178.6(4) . . . . ?
C5 C21 C26 C25 178.7(3) . . . . ?
C5 C21 C26 C27 -2.1(5) . . . . ?
C6 N2 C9 C8 0.2(4) . . . . ?
C6 N2 C9 C15 -177.7(3) . . . . ?
C6 C5 C21 C22 -87.4(5) . . . . ?
C6 C5 C21 C26 93.5(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C6 C7 C8 C16 -179.1(4) . . . . ?
C7 C8 C9 N2 -0.2(4) . . . . ?
C7 C8 C9 C15 177.5(4) . . . . ?
C7 C8 C16 C17 -176.6(5) . . . . ?
C8 C16 C17 C18 -179.4(4) . . . . ?
C9 N2 C6 C5 179.1(3) . . . . ?
C9 N2 C6 C7 -0.1(4) . . . . ?
C9 C8 C16 C17 4.3(7) . . . . ?
C10 C1 C2 C3 -178.7(4) . . . . ?
C10 C1 C2 C11 1.6(7) . . . . ?
C11 C2 C3 C4 179.5(4) . . . . ?
C11 C2 C3 C13 1.5(6) . . . . ?
C13 C3 C4 N1 178.0(4) . . . . ?
C13 C3 C4 C5 -1.4(7) . . . . ?
C14 C7 C8 C9 179.0(4) . . . . ?
C14 C7 C8 C16 -0.2(6) . . . . ?
C16 C8 C9 N2 179.0(4) . . . . ?
C16 C8 C9 C15 -3.2(6) . . . . ?
C16 C17 C18 O1 1.8(9) . . . . ?
C16 C17 C18 O2 -175.8(4) . . . . ?
C16 C17 C18 O2A 144.7(7) . . . . ?
C16 C17 C18 O1A -18(2) . . . . ?
C17 C18 O2A C19A -175.8(13) . . . . ?
C18 O2 C19 C20 85.9(6) . . . . ?
C18 O2A C19A C20A -62(3) . . . . ?
C19 O2 C18 O1 4.0(8) . . . . ?
C19 O2 C18 C17 -178.3(4) . . . . ?
C19 O2 C18 O2A -93.4(9) . . . . ?
C19 O2 C18 O1A 25(2) . . . . ?
C21 C5 C6 N2 -174.9(3) . . . . ?
C21 C5 C6 C7 4.1(6) . . . . ?
C21 C22 C23 C24 0.1(6) . . . . ?
C22 C21 C26 C25 -0.4(5) . . . . ?
C22 C21 C26 C27 178.7(4) . . . . ?
C22 C23 C24 C25 -0.8(6) . . . . ?
C23 C24 C25 C26 0.9(6) . . . . ?
C24 C25 C26 C21 -0.3(6) . . . . ?
C24 C25 C26 C27 -179.4(4) . . . . ?
C26 C21 C22 C23 0.5(6) . . . . ?
O1A C18 O2A C19A -16(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 984418'
