# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H28 B N'
_chemical_formula_sum            'C21 H28 B N'
_chemical_formula_weight         305.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.5601(10)
_cell_length_b                   11.2810(9)
_cell_length_c                   12.2599(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.667(6)
_cell_angle_gamma                90
_cell_volume                     1787.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    26662
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.064
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.130
-1 0 0 0.175
0 -1 1 0.090
0 1 -1 0.119
0 -1 -1 0.145
0 1 1 0.046


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26459
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4067
_reflns_number_gt                3159
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0413P)²+0.8990P] 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         4067
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25461(9) 0.34927(10) 0.07791(10) 0.0186(3) Uani 1 1 d . . .
C1 C 0.23897(11) 0.14131(13) 0.10422(12) 0.0192(3) Uani 1 1 d . . .
C17 C 0.11445(11) 0.35678(13) 0.26870(12) 0.0223(3) Uani 1 1 d . . .
H17 H 0.1746 0.4006 0.2993 0.027 Uiso 1 1 d R . .
C16 C 0.10476(11) 0.28605(12) 0.17245(12) 0.0195(3) Uani 1 1 d . . .
C2 C 0.31910(11) 0.15922(13) 0.05619(11) 0.0186(3) Uani 1 1 d . . .
C12 C 0.21271(11) 0.46494(12) 0.02054(12) 0.0210(3) Uani 1 1 d . . .
C18 C 0.03606(12) 0.36320(14) 0.32015(13) 0.0262(3) Uani 1 1 d . . .
H18 H 0.0441 0.4114 0.3838 0.031 Uiso 1 1 d R . .
C21 C 0.01294(11) 0.22036(13) 0.13094(13) 0.0225(3) Uani 1 1 d . . .
H21 H 0.0043 0.1715 0.0677 0.027 Uiso 1 1 d R . .
C20 C -0.06522(12) 0.22640(14) 0.18215(14) 0.0258(3) Uani 1 1 d . . .
H20 H -0.1254 0.1822 0.1529 0.031 Uiso 1 1 d R . .
C6 C 0.20481(11) 0.02672(13) 0.11464(13) 0.0231(3) Uani 1 1 d . . .
H6 H 0.1541 0.0138 0.1501 0.028 Uiso 1 1 d R . .
C9 C 0.43992(12) 0.26915(15) 0.27602(13) 0.0275(3) Uani 1 1 d . . .
H9A H 0.5027 0.2858 0.3361 0.033 Uiso 1 1 d R . .
H9B H 0.4278 0.1852 0.2716 0.033 Uiso 1 1 d R . .
H9C H 0.3830 0.3086 0.2919 0.033 Uiso 1 1 d R . .
C19 C -0.05363(12) 0.29820(14) 0.27675(13) 0.0264(3) Uani 1 1 d . . .
H19 H -0.1060 0.3028 0.3110 0.032 Uiso 1 1 d R . .
B1 B 0.19653(12) 0.26676(15) 0.12079(13) 0.0192(3) Uani 1 1 d . . .
C4 C 0.32372(12) -0.04869(14) 0.02011(13) 0.0255(3) Uani 1 1 d . . .
H4 H 0.3498 -0.1124 -0.0107 0.031 Uiso 1 1 d R . .
C5 C 0.24718(12) -0.06825(14) 0.07192(13) 0.0261(3) Uani 1 1 d . . .
H5 H 0.2241 -0.1449 0.0778 0.031 Uiso 1 1 d R . .
C14 C 0.20520(14) 0.55803(14) 0.10816(15) 0.0315(4) Uani 1 1 d . . .
H14A H 0.1581 0.5313 0.1476 0.038 Uiso 1 1 d R . .
H14B H 0.1805 0.6312 0.0695 0.038 Uiso 1 1 d R . .
H14C H 0.2723 0.5702 0.1623 0.038 Uiso 1 1 d R . .
C3 C 0.36194(11) 0.06464(13) 0.01362(12) 0.0221(3) Uani 1 1 d . . .
H3 H 0.4151 0.0769 -0.0185 0.027 Uiso 1 1 d R . .
C7 C 0.34739(10) 0.28980(12) 0.06088(12) 0.0184(3) Uani 1 1 d . . .
H7 H 0.3564 0.3146 -0.0121 0.022 Uiso 1 1 d R . .
C8 C 0.45001(11) 0.31328(13) 0.16179(12) 0.0213(3) Uani 1 1 d . . .
C15 C 0.10411(12) 0.44100(14) -0.06148(14) 0.0280(3) Uani 1 1 d . . .
H15A H 0.1084 0.3845 -0.1184 0.034 Uiso 1 1 d R . .
H15B H 0.0751 0.5137 -0.0981 0.034 Uiso 1 1 d R . .
H15C H 0.0608 0.4100 -0.0192 0.034 Uiso 1 1 d R . .
C11 C 0.47802(12) 0.44474(14) 0.17426(14) 0.0301(4) Uani 1 1 d . . .
H11A H 0.4228 0.4885 0.1893 0.036 Uiso 1 1 d R . .
H11B H 0.4885 0.4731 0.1048 0.036 Uiso 1 1 d R . .
H11C H 0.5404 0.4553 0.2366 0.036 Uiso 1 1 d R . .
C10 C 0.54036(12) 0.24858(15) 0.13669(15) 0.0295(4) Uani 1 1 d . . .
H10A H 0.5435 0.2708 0.0623 0.035 Uiso 1 1 d R . .
H10B H 0.5301 0.1645 0.1389 0.035 Uiso 1 1 d R . .
H10C H 0.6040 0.2699 0.1934 0.035 Uiso 1 1 d R . .
C13 C 0.27623(13) 0.51529(15) -0.05306(15) 0.0321(4) Uani 1 1 d . . .
H13A H 0.3448 0.5339 -0.0051 0.038 Uiso 1 1 d R . .
H13B H 0.2435 0.5859 -0.0909 0.038 Uiso 1 1 d R . .
H13C H 0.2801 0.4576 -0.1092 0.038 Uiso 1 1 d 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
N1 B1 1.419(2) . ?
N1 C7 1.4953(17) . ?
N1 C12 1.5092(18) . ?
C1 C6 1.392(2) . ?
C1 C2 1.3987(19) . ?
C1 B1 1.564(2) . ?
C17 C18 1.393(2) . ?
C17 C16 1.397(2) . ?
C17 H17 0.9299 . ?
C16 C21 1.405(2) . ?
C16 B1 1.573(2) . ?
C2 C3 1.390(2) . ?
C2 C7 1.5189(19) . ?
C12 C14 1.527(2) . ?
C12 C13 1.533(2) . ?
C12 C15 1.534(2) . ?
C18 C19 1.381(2) . ?
C18 H18 0.9301 . ?
C21 C20 1.388(2) . ?
C21 H21 0.9299 . ?
C20 C19 1.384(2) . ?
C20 H20 0.9300 . ?
C6 C5 1.391(2) . ?
C6 H6 0.9300 . ?
C9 C8 1.531(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C19 H19 0.9299 . ?
C4 C5 1.389(2) . ?
C4 C3 1.391(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9301 . ?
C14 H14A 0.9599 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 H3 0.9301 . ?
C7 C8 1.5786(19) . ?
C7 H7 0.9800 . ?
C8 C11 1.527(2) . ?
C8 C10 1.535(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C11 H11A 0.9601 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9601 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9601 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9599 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 N1 C7 110.02(11) . . ?
B1 N1 C12 124.54(11) . . ?
C7 N1 C12 122.45(11) . . ?
C6 C1 C2 119.69(13) . . ?
C6 C1 B1 133.04(13) . . ?
C2 C1 B1 106.71(12) . . ?
C18 C17 C16 121.54(14) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.3 . . ?
C17 C16 C21 116.93(13) . . ?
C17 C16 B1 122.40(13) . . ?
C21 C16 B1 120.23(13) . . ?
C3 C2 C1 120.91(13) . . ?
C3 C2 C7 128.98(13) . . ?
C1 C2 C7 110.10(12) . . ?
N1 C12 C14 111.27(12) . . ?
N1 C12 C13 113.29(12) . . ?
C14 C12 C13 109.18(13) . . ?
N1 C12 C15 107.69(11) . . ?
C14 C12 C15 109.05(13) . . ?
C13 C12 C15 106.16(12) . . ?
C19 C18 C17 120.11(14) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 120.0 . . ?
C20 C21 C16 121.66(14) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.2 . . ?
C19 C20 C21 119.98(14) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C5 C6 C1 119.58(14) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.6 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C18 C19 C20 119.77(14) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.2 . . ?
N1 B1 C1 106.14(12) . . ?
N1 B1 C16 130.84(13) . . ?
C1 B1 C16 123.00(13) . . ?
C5 C4 C3 121.02(14) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.08(14) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 119.9 . . ?
C12 C14 H14A 109.6 . . ?
C12 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 C4 118.60(14) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
N1 C7 C2 103.11(11) . . ?
N1 C7 C8 113.21(11) . . ?
C2 C7 C8 110.18(11) . . ?
N1 C7 H7 110.0 . . ?
C2 C7 H7 110.0 . . ?
C8 C7 H7 110.1 . . ?
C11 C8 C9 108.22(13) . . ?
C11 C8 C10 107.00(13) . . ?
C9 C8 C10 109.08(13) . . ?
C11 C8 C7 112.01(12) . . ?
C9 C8 C7 111.10(12) . . ?
C10 C8 C7 109.29(12) . . ?
C12 C15 H15A 109.6 . . ?
C12 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C10 H10A 109.6 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.4 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 999425'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 B N'
_chemical_formula_sum            'C18 H22 B N'
_chemical_formula_weight         263.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-p 1'

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

_cell_length_a                   8.8771(3)
_cell_length_b                   9.2700(3)
_cell_length_c                   9.7179(3)
_cell_angle_alpha                74.766(3)
_cell_angle_beta                 76.770(4)
_cell_angle_gamma                82.477(4)
_cell_volume                     748.98(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    8014
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.066
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.078
0 0 -1 0.136
0 1 0 0.143
0 -1 0 0.195
1 0 0 0.049
-1 0 0 0.176


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7972
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.40
_reflns_number_total             3336
_reflns_number_gt                2747
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0360P)²+0.3948P] 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         3336
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.69477(14) 0.22236(14) 0.62783(13) 0.0199(3) Uani 1 1 d . . .
C16 C 0.18869(18) 0.39338(19) 1.00747(16) 0.0278(3) Uani 1 1 d . . .
H16 H 0.1145 0.4211 1.0824 0.033 Uiso 1 1 d R . .
C1 C 0.47864(17) 0.23666(16) 0.51661(16) 0.0205(3) Uani 1 1 d . . .
C13 C 0.41561(16) 0.30827(16) 0.78211(15) 0.0206(3) Uani 1 1 d . . .
C9 C 0.80504(17) 0.20998(17) 0.72588(17) 0.0231(3) Uani 1 1 d . . .
C15 C 0.17619(18) 0.2655(2) 0.96465(17) 0.0289(4) Uani 1 1 d . . .
H15 H 0.0932 0.2068 1.0106 0.035 Uiso 1 1 d R . .
C3 C 0.60321(19) 0.15650(17) 0.29560(17) 0.0262(3) Uani 1 1 d . . .
H3 H 0.6923 0.1249 0.2361 0.031 Uiso 1 1 d R . .
C6 C 0.33530(18) 0.25188(17) 0.47601(17) 0.0246(3) Uani 1 1 d . . .
H6 H 0.2462 0.2842 0.5350 0.030 Uiso 1 1 d R . .
C18 C 0.42438(18) 0.43779(18) 0.82682(17) 0.0248(3) Uani 1 1 d . . .
H18 H 0.5068 0.4972 0.7811 0.030 Uiso 1 1 d R . .
C11 C 0.86908(19) 0.36234(18) 0.70420(19) 0.0294(4) Uani 1 1 d . . .
H11A H 0.9239 0.3948 0.6054 0.035 Uiso 1 1 d R . .
H11B H 0.9385 0.3528 0.7692 0.035 Uiso 1 1 d R . .
H11C H 0.7846 0.4347 0.7246 0.035 Uiso 1 1 d R . .
C8 C 0.86276(18) 0.3030(2) 0.37686(18) 0.0303(4) Uani 1 1 d . . .
H8A H 0.8101 0.4013 0.3664 0.036 Uiso 1 1 d R . .
H8B H 0.8910 0.2786 0.2838 0.036 Uiso 1 1 d R . .
H8C H 0.9546 0.3009 0.4139 0.036 Uiso 1 1 d R . .
C14 C 0.28814(18) 0.22407(18) 0.85269(17) 0.0257(3) Uani 1 1 d . . .
H14 H 0.2776 0.1384 0.8240 0.031 Uiso 1 1 d R . .
C4 C 0.4597(2) 0.17035(18) 0.25763(18) 0.0289(4) Uani 1 1 d . . .
H4 H 0.4523 0.1475 0.1719 0.035 Uiso 1 1 d R . .
C12 C 0.94012(18) 0.09184(19) 0.69841(19) 0.0296(4) Uani 1 1 d . . .
H12A H 0.8996 -0.0031 0.7120 0.035 Uiso 1 1 d R . .
H12B H 1.0071 0.0827 0.7655 0.035 Uiso 1 1 d R . .
H12C H 0.9978 0.1223 0.6005 0.035 Uiso 1 1 d R . .
C10 C 0.72179(19) 0.15739(19) 0.88483(17) 0.0283(3) Uani 1 1 d . . .
H10A H 0.6392 0.2305 0.9078 0.034 Uiso 1 1 d R . .
H10B H 0.7940 0.1458 0.9476 0.034 Uiso 1 1 d R . .
H10C H 0.6798 0.0631 0.8987 0.034 Uiso 1 1 d R . .
C2 C 0.61089(17) 0.19037(16) 0.42467(16) 0.0217(3) Uani 1 1 d . . .
C17 C 0.31266(19) 0.48035(18) 0.93787(17) 0.0283(3) Uani 1 1 d . . .
H17 H 0.3213 0.5672 0.9655 0.034 Uiso 1 1 d R . .
C7 C 0.75485(17) 0.18827(17) 0.48279(16) 0.0226(3) Uani 1 1 d . . .
H7 H 0.8088 0.0879 0.4951 0.027 Uiso 1 1 d R . .
C5 C 0.32676(19) 0.21840(18) 0.34685(17) 0.0274(3) Uani 1 1 d . . .
H5 H 0.2314 0.2283 0.3196 0.033 Uiso 1 1 d R . .
B1 B 0.53226(19) 0.25908(18) 0.65113(18) 0.0201(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
N1 B1 1.418(2) . ?
N1 C7 1.4889(18) . ?
N1 C9 1.4897(19) . ?
C16 C15 1.380(2) . ?
C16 C17 1.387(2) . ?
C16 H16 0.9300 . ?
C1 C6 1.396(2) . ?
C1 C2 1.396(2) . ?
C1 B1 1.560(2) . ?
C13 C18 1.397(2) . ?
C13 C14 1.398(2) . ?
C13 B1 1.574(2) . ?
C9 C10 1.532(2) . ?
C9 C11 1.537(2) . ?
C9 C12 1.540(2) . ?
C15 C14 1.394(2) . ?
C15 H15 0.9300 . ?
C3 C4 1.386(2) . ?
C3 C2 1.389(2) . ?
C3 H3 0.9300 . ?
C6 C5 1.390(2) . ?
C6 H6 0.9300 . ?
C18 C17 1.391(2) . ?
C18 H18 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9599 . ?
C11 H11C 0.9600 . ?
C8 C7 1.532(2) . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C14 H14 0.9300 . ?
C4 C5 1.393(2) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 C7 1.507(2) . ?
C17 H17 0.9300 . ?
C7 H7 0.9800 . ?
C5 H5 0.9301 . ?

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
B1 N1 C7 111.23(12) . . ?
B1 N1 C9 129.92(13) . . ?
C7 N1 C9 118.82(11) . . ?
C15 C16 C17 119.54(14) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.2 . . ?
C6 C1 C2 118.94(14) . . ?
C6 C1 B1 134.10(14) . . ?
C2 C1 B1 106.96(13) . . ?
C18 C13 C14 116.99(13) . . ?
C18 C13 B1 124.18(13) . . ?
C14 C13 B1 118.67(13) . . ?
N1 C9 C10 109.70(12) . . ?
N1 C9 C11 110.53(12) . . ?
C10 C9 C11 109.10(13) . . ?
N1 C9 C12 111.00(12) . . ?
C10 C9 C12 106.66(13) . . ?
C11 C9 C12 109.75(13) . . ?
C16 C15 C14 120.03(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 119.9 . . ?
C4 C3 C2 118.55(15) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C6 C1 119.53(14) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.2 . . ?
C17 C18 C13 121.66(14) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
C9 C11 H11A 109.6 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.3 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.6 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C14 C13 121.69(15) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.2 . . ?
C3 C4 C5 120.48(14) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.8 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.6 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 C1 121.84(14) . . ?
C3 C2 C7 126.94(14) . . ?
C1 C2 C7 111.20(13) . . ?
C16 C17 C18 120.09(15) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 119.9 . . ?
N1 C7 C2 104.07(11) . . ?
N1 C7 C8 113.71(12) . . ?
C2 C7 C8 109.83(12) . . ?
N1 C7 H7 109.7 . . ?
C2 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C6 C5 C4 120.65(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.6 . . ?
N1 B1 C1 106.16(13) . . ?
N1 B1 C13 131.26(14) . . ?
C1 B1 C13 122.55(13) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 999426'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H31 B N2'
_chemical_formula_sum            'C29 H31 B N2'
_chemical_formula_weight         418.37

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   16.5759(8)
_cell_length_b                   10.0011(11)
_cell_length_c                   14.4270(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.314(4)
_cell_angle_gamma                90
_cell_volume                     2391.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    23684
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.067
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.205
1 0 0 0.198
0 -1 1 0.117
0 1 -1 0.162
0 0 1 0.119
0 0 -1 0.163
0 -1 -1 0.173
0 1 1 0.227
1 1 1 0.230
-1 -1 -1 0.199


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23632
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5371
_reflns_number_gt                4207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0310P)²+1.4361P] 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         5371
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.25742(9) -0.03405(15) 0.80960(10) 0.0232(3) Uani 1 1 d . . .
N2 N 0.23130(7) 0.16355(12) 0.90341(8) 0.0195(3) Uani 1 1 d . . .
C6 C 0.26819(8) 0.03512(14) 0.89366(10) 0.0197(3) Uani 1 1 d . . .
N1 N 0.20270(7) 0.38696(13) 0.90130(9) 0.0232(3) Uani 1 1 d . . .
C24 C 0.11857(8) 0.09944(16) 1.00882(10) 0.0229(3) Uani 1 1 d . . .
C5 C 0.14320(8) 0.17384(15) 0.92213(10) 0.0220(3) Uani 1 1 d . . .
H5 H 0.1130 0.1366 0.8689 0.026 Uiso 1 1 d R . .
C18 C 0.35710(9) 0.31987(16) 0.87110(11) 0.0247(3) Uani 1 1 d . . .
C29 C 0.10367(9) -0.03678(16) 1.00299(12) 0.0286(3) Uani 1 1 d . . .
H29 H 0.1089 -0.0802 0.9464 0.034 Uiso 1 1 d R . .
C1 C 0.13186(9) 0.32309(15) 0.92212(10) 0.0219(3) Uani 1 1 d . . .
C11 C 0.31676(9) -0.01629(16) 0.96630(11) 0.0252(3) Uani 1 1 d . . .
C28 C 0.08101(10) -0.10916(19) 1.08007(13) 0.0353(4) Uani 1 1 d . . .
H28 H 0.0717 -0.2006 1.0751 0.042 Uiso 1 1 d R . .
C10 C 0.35532(10) -0.13791(18) 0.95204(13) 0.0338(4) Uani 1 1 d . . .
H10 H 0.3886 -0.1731 0.9987 0.041 Uiso 1 1 d R . .
C8 C 0.29576(10) -0.15671(16) 0.80003(12) 0.0307(4) Uani 1 1 d . . .
H8 H 0.2881 -0.2055 0.7456 0.037 Uiso 1 1 d R . .
C3 C 0.10880(10) 0.54286(16) 0.91670(11) 0.0282(3) Uani 1 1 d . . .
H3 H 0.0829 0.6252 0.9191 0.034 Uiso 1 1 d R . .
C23 C 0.39201(10) 0.43814(17) 0.90332(12) 0.0308(4) Uani 1 1 d . . .
H23 H 0.3610 0.4979 0.9368 0.037 Uiso 1 1 d R . .
B1 B 0.26714(10) 0.28917(18) 0.89089(12) 0.0232(3) Uani 1 1 d . . .
C4 C 0.18797(10) 0.52268(16) 0.89789(11) 0.0280(3) Uani 1 1 d . . .
H4 H 0.2256 0.5887 0.8849 0.034 Uiso 1 1 d R . .
C19 C 0.40633(9) 0.23175(17) 0.82223(11) 0.0287(3) Uani 1 1 d . . .
H19 H 0.3849 0.1515 0.8003 0.034 Uiso 1 1 d R . .
C9 C 0.34508(10) -0.20700(17) 0.86997(13) 0.0361(4) Uani 1 1 d . . .
H9 H 0.3715 -0.2880 0.8617 0.043 Uiso 1 1 d R . .
C12 C 0.20818(10) 0.02212(18) 0.72809(11) 0.0312(4) Uani 1 1 d . . .
H12 H 0.1904 0.1121 0.7450 0.037 Uiso 1 1 d R . .
C20 C 0.48621(10) 0.26209(19) 0.80590(12) 0.0349(4) Uani 1 1 d . . .
H20 H 0.5180 0.2020 0.7738 0.042 Uiso 1 1 d R . .
C2 C 0.07269(10) 0.41629(17) 0.93214(11) 0.0283(3) Uani 1 1 d . . .
H2 H 0.0191 0.4002 0.9464 0.034 Uiso 1 1 d R . .
C21 C 0.51867(10) 0.3807(2) 0.83721(14) 0.0411(5) Uani 1 1 d . . .
H21 H 0.5721 0.4017 0.8251 0.049 Uiso 1 1 d R . .
C15 C 0.32997(10) 0.05680(19) 1.05775(11) 0.0329(4) Uani 1 1 d . . .
H15 H 0.2951 0.1360 1.0570 0.039 Uiso 1 1 d R . .
C25 C 0.11001(10) 0.16207(18) 1.09382(11) 0.0321(4) Uani 1 1 d . . .
H25 H 0.1197 0.2534 1.0993 0.039 Uiso 1 1 d R . .
C14 C 0.25879(12) 0.0342(2) 0.64104(12) 0.0450(5) Uani 1 1 d . . .
H14A H 0.3048 0.0899 0.6540 0.054 Uiso 1 1 d R . .
H14B H 0.2267 0.0731 0.5919 0.054 Uiso 1 1 d R . .
H14C H 0.2766 -0.0530 0.6226 0.054 Uiso 1 1 d R . .
C22 C 0.47208(11) 0.46879(19) 0.88651(14) 0.0394(4) Uani 1 1 d . . .
H22 H 0.4942 0.5484 0.9085 0.047 Uiso 1 1 d R . .
C17 C 0.41729(11) 0.1042(2) 1.06950(13) 0.0432(5) Uani 1 1 d . . .
H17A H 0.4527 0.0282 1.0714 0.052 Uiso 1 1 d R . .
H17B H 0.4232 0.1537 1.1262 0.052 Uiso 1 1 d R . .
H17C H 0.4308 0.1605 1.0182 0.052 Uiso 1 1 d R . .
C27 C 0.07259(11) -0.0459(2) 1.16399(13) 0.0395(4) Uani 1 1 d . . .
H27 H 0.0572 -0.0941 1.2158 0.047 Uiso 1 1 d R . .
C26 C 0.08714(12) 0.0894(2) 1.17100(12) 0.0405(4) Uani 1 1 d . . .
H26 H 0.0814 0.1324 1.2276 0.049 Uiso 1 1 d R . .
C16 C 0.30669(12) -0.0302(2) 1.14010(13) 0.0463(5) Uani 1 1 d . . .
H16A H 0.2515 -0.0578 1.1325 0.056 Uiso 1 1 d R . .
H16B H 0.3130 0.0206 1.1963 0.056 Uiso 1 1 d R . .
H16C H 0.3409 -0.1076 1.1432 0.056 Uiso 1 1 d R . .
C13 C 0.13350(12) -0.0619(3) 0.70787(16) 0.0551(6) Uani 1 1 d . . .
H13A H 0.1494 -0.1504 0.6899 0.066 Uiso 1 1 d R . .
H13B H 0.1024 -0.0215 0.6584 0.066 Uiso 1 1 d R . .
H13C H 0.1016 -0.0668 0.7624 0.066 Uiso 1 1 d 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
C7 C8 1.390(2) . ?
C7 C6 1.404(2) . ?
C7 C12 1.523(2) . ?
N2 B1 1.403(2) . ?
N2 C6 1.4309(19) . ?
N2 C5 1.4948(18) . ?
C6 C11 1.404(2) . ?
N1 C1 1.3760(19) . ?
N1 C4 1.380(2) . ?
N1 B1 1.458(2) . ?
C24 C29 1.387(2) . ?
C24 C25 1.387(2) . ?
C24 C5 1.519(2) . ?
C5 C1 1.504(2) . ?
C5 H5 0.9800 . ?
C18 C23 1.392(2) . ?
C18 C19 1.402(2) . ?
C18 B1 1.555(2) . ?
C29 C28 1.386(2) . ?
C29 H29 0.9301 . ?
C1 C2 1.363(2) . ?
C11 C10 1.392(2) . ?
C11 C15 1.520(2) . ?
C28 C27 1.376(3) . ?
C28 H28 0.9300 . ?
C10 C9 1.378(3) . ?
C10 H10 0.9300 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9299 . ?
C3 C4 1.361(2) . ?
C3 C2 1.420(2) . ?
C3 H3 0.9300 . ?
C23 C22 1.389(2) . ?
C23 H23 0.9300 . ?
C4 H4 0.9299 . ?
C19 C20 1.384(2) . ?
C19 H19 0.9300 . ?
C9 H9 0.9301 . ?
C12 C13 1.519(3) . ?
C12 C14 1.531(2) . ?
C12 H12 0.9800 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9299 . ?
C2 H2 0.9299 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9300 . ?
C15 C17 1.529(2) . ?
C15 C16 1.529(3) . ?
C15 H15 0.9801 . ?
C25 C26 1.389(2) . ?
C25 H25 0.9301 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9599 . ?
C14 H14C 0.9600 . ?
C22 H22 0.9300 . ?
C17 H17A 0.9599 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C27 C26 1.378(3) . ?
C27 H27 0.9301 . ?
C26 H26 0.9300 . ?
C16 H16A 0.9601 . ?
C16 H16B 0.9601 . ?
C16 H16C 0.9600 . ?
C13 H13A 0.9601 . ?
C13 H13B 0.9598 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C7 C6 118.12(14) . . ?
C8 C7 C12 119.14(14) . . ?
C6 C7 C12 122.71(14) . . ?
B1 N2 C6 127.44(12) . . ?
B1 N2 C5 112.33(12) . . ?
C6 N2 C5 120.06(12) . . ?
C7 C6 C11 121.57(14) . . ?
C7 C6 N2 118.75(13) . . ?
C11 C6 N2 119.62(13) . . ?
C1 N1 C4 108.25(13) . . ?
C1 N1 B1 109.99(13) . . ?
C4 N1 B1 141.76(14) . . ?
C29 C24 C25 118.39(15) . . ?
C29 C24 C5 118.82(14) . . ?
C25 C24 C5 122.79(14) . . ?
N2 C5 C1 101.00(11) . . ?
N2 C5 C24 113.40(12) . . ?
C1 C5 C24 116.75(12) . . ?
N2 C5 H5 108.4 . . ?
C1 C5 H5 108.4 . . ?
C24 C5 H5 108.4 . . ?
C23 C18 C19 117.37(14) . . ?
C23 C18 B1 119.95(14) . . ?
C19 C18 B1 122.67(14) . . ?
C28 C29 C24 121.03(16) . . ?
C28 C29 H29 119.5 . . ?
C24 C29 H29 119.5 . . ?
C2 C1 N1 108.99(14) . . ?
C2 C1 C5 140.22(14) . . ?
N1 C1 C5 110.70(12) . . ?
C10 C11 C6 117.85(15) . . ?
C10 C11 C15 119.42(14) . . ?
C6 C11 C15 122.71(14) . . ?
C27 C28 C29 120.04(17) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C9 C10 C11 121.15(16) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C9 C8 C7 120.93(16) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C4 C3 C2 108.11(14) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 126.0 . . ?
C22 C23 C18 121.38(16) . . ?
C22 C23 H23 119.3 . . ?
C18 C23 H23 119.3 . . ?
N2 B1 N1 105.90(13) . . ?
N2 B1 C18 127.65(14) . . ?
N1 B1 C18 126.44(14) . . ?
C3 C4 N1 108.03(14) . . ?
C3 C4 H4 126.1 . . ?
N1 C4 H4 125.9 . . ?
C20 C19 C18 121.20(16) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C10 C9 C8 120.34(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C13 C12 C7 111.35(16) . . ?
C13 C12 C14 110.21(16) . . ?
C7 C12 C14 111.61(13) . . ?
C13 C12 H12 107.9 . . ?
C7 C12 H12 107.8 . . ?
C14 C12 H12 107.8 . . ?
C21 C20 C19 120.14(17) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C1 C2 C3 106.62(14) . . ?
C1 C2 H2 126.7 . . ?
C3 C2 H2 126.7 . . ?
C20 C21 C22 120.06(16) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C11 C15 C17 111.25(14) . . ?
C11 C15 C16 111.54(16) . . ?
C17 C15 C16 110.21(14) . . ?
C11 C15 H15 107.8 . . ?
C17 C15 H15 107.9 . . ?
C16 C15 H15 108.0 . . ?
C24 C25 C26 120.51(17) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.7 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C22 C23 119.85(17) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.0 . . ?
C15 C17 H17A 109.6 . . ?
C15 C17 H17B 109.4 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C28 C27 C26 119.68(16) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.1 . . ?
C27 C26 C25 120.35(17) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.9 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.6 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 999427'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H32 B N'
_chemical_formula_sum            'C31 H32 B N'
_chemical_formula_weight         429.39

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   20.1420(19)
_cell_length_b                   9.9090(11)
_cell_length_c                   37.433(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.702(6)
_cell_angle_gamma                90
_cell_volume                     7403.7(12)
_cell_formula_units_Z            12
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    45778
_cell_measurement_theta_min      1
_cell_measurement_theta_max      26.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2760
_exptl_absorpt_coefficient_mu    0.065
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.158
-1 0 0 0.064
1 1 0 0.158
-1 -1 0 0.099
0 0 1 0.103
0 0 -1 0.119
1 0 -1 0.129
-1 0 1 0.084


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45732
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.75
_reflns_number_total             13911
_reflns_number_gt                9787
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0248P)²+6.2865P] 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     SHELXL
_refine_ls_extinction_coef       0.00158(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         13911
_refine_ls_number_parameters     893
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.58739(9) -0.67076(18) 0.66516(5) 0.0225(4) Uani 1 1 d . . .
C208 C 0.83419(12) -0.5733(2) 0.83268(6) 0.0237(5) Uani 1 1 d . . .
N1 N 0.74465(9) -0.49245(19) 0.48797(5) 0.0229(4) Uani 1 1 d . . .
C108 C 0.54887(11) -0.7933(2) 0.66013(6) 0.0239(5) Uani 1 1 d . . .
C8 C 0.78338(11) -0.3700(2) 0.49026(6) 0.0251(5) Uani 1 1 d . . .
C113 C 0.53653(12) -0.8672(2) 0.69045(7) 0.0283(6) Uani 1 1 d . . .
N3 N 0.87187(9) -0.55482(19) 0.80285(5) 0.0236(4) Uani 1 1 d . . .
C220 C 0.84887(12) -0.7889(2) 0.76870(6) 0.0260(5) Uani 1 1 d . . .
C209 C 0.76604(12) -0.5371(2) 0.82774(6) 0.0257(5) Uani 1 1 d . . .
C1 C 0.70178(12) -0.7144(2) 0.48231(6) 0.0245(5) Uani 1 1 d . . .
C3 C 0.58182(12) -0.6708(3) 0.47271(6) 0.0303(6) Uani 1 1 d . . .
H3 H 0.5462 -0.6103 0.4710 0.036 Uiso 1 1 d R . .
C213 C 0.86392(12) -0.6318(2) 0.86495(6) 0.0279(6) Uani 1 1 d . . .
C202 C 0.91755(11) -0.4226(2) 0.76025(6) 0.0261(5) Uani 1 1 d . . .
C231 C 1.01826(13) -0.4317(3) 0.82643(7) 0.0326(6) Uani 1 1 d . . .
H231 H 1.0248 -0.4992 0.8100 0.039 Uiso 1 1 d R . .
C26 C 0.64636(11) -0.4013(2) 0.51429(6) 0.0237(5) Uani 1 1 d . . .
C109 C 0.52300(12) -0.8334(2) 0.62520(7) 0.0282(6) Uani 1 1 d . . .
C120 C 0.48820(12) -0.4961(2) 0.65541(6) 0.0267(5) Uani 1 1 d . . .
C9 C 0.81619(12) -0.3261(2) 0.52366(7) 0.0303(6) Uani 1 1 d . . .
C2 C 0.64734(12) -0.6253(2) 0.47963(6) 0.0240(5) Uani 1 1 d . . .
C102 C 0.68163(12) -0.5325(2) 0.67806(6) 0.0273(5) Uani 1 1 d . . .
C131 C 0.71591(13) -0.6951(3) 0.61604(7) 0.0352(6) Uani 1 1 d . . .
H131 H 0.7109 -0.6023 0.6131 0.042 Uiso 1 1 d R . .
C14 C 0.81483(13) -0.4028(3) 0.55851(7) 0.0345(6) Uani 1 1 d . . .
H14 H 0.7830 -0.4775 0.5537 0.041 Uiso 1 1 d R . .
C7 C 0.67027(12) -0.4800(2) 0.48362(6) 0.0256(5) Uani 1 1 d . . .
H7 H 0.6555 -0.4326 0.4610 0.031 Uiso 1 1 d R . .
C114 C 0.53761(13) -0.7592(3) 0.59174(6) 0.0322(6) Uani 1 1 d . . .
H114 H 0.5697 -0.6873 0.5995 0.039 Uiso 1 1 d R . .
C226 C 0.95544(12) -0.3736(2) 0.82557(6) 0.0265(5) Uani 1 1 d . . .
C227 C 0.94749(14) -0.2710(3) 0.84971(7) 0.0364(6) Uani 1 1 d . . .
H227 H 0.9061 -0.2290 0.8492 0.044 Uiso 1 1 d R . .
C13 C 0.78693(12) -0.2962(2) 0.45857(7) 0.0304(6) Uani 1 1 d . . .
C125 C 0.43676(12) -0.5638(3) 0.66946(7) 0.0320(6) Uani 1 1 d . . .
H125 H 0.4472 -0.6373 0.6846 0.038 Uiso 1 1 d R . .
C214 C 0.73104(12) -0.4768(2) 0.79302(6) 0.0300(6) Uani 1 1 d . . .
H214 H 0.7647 -0.4639 0.7767 0.036 Uiso 1 1 d R . .
C27 C 0.64464(12) -0.2611(2) 0.51266(6) 0.0276(5) Uani 1 1 d . . .
H27 H 0.6566 -0.2173 0.4925 0.033 Uiso 1 1 d R . .
C4 C 0.57066(13) -0.8081(3) 0.46840(7) 0.0342(6) Uani 1 1 d . . .
H4 H 0.5270 -0.8404 0.4637 0.041 Uiso 1 1 d R . .
C128 C 0.73245(14) -0.9699(3) 0.62408(7) 0.0399(7) Uani 1 1 d . . .
H128 H 0.7377 -1.0627 0.6269 0.048 Uiso 1 1 d R . .
C121 C 0.46899(14) -0.3882(2) 0.63226(7) 0.0341(6) Uani 1 1 d . . .
H121 H 0.5018 -0.3391 0.6227 0.041 Uiso 1 1 d R . .
C31 C 0.62845(12) -0.4639(3) 0.54466(6) 0.0316(6) Uani 1 1 d . . .
H31 H 0.6293 -0.5575 0.5463 0.038 Uiso 1 1 d R . .
C20 C 0.84113(12) -0.6726(2) 0.49395(6) 0.0293(6) Uani 1 1 d . . .
C127 C 0.70348(13) -0.8956(3) 0.64916(7) 0.0347(6) Uani 1 1 d . . .
H127 H 0.6897 -0.9393 0.6689 0.042 Uiso 1 1 d R . .
B3 B 0.87488(13) -0.6396(3) 0.77288(7) 0.0252(6) Uani 1 1 d . . .
B2 B 0.56305(15) -0.5378(3) 0.66419(7) 0.0280(6) Uani 1 1 d . . .
C126 C 0.69452(12) -0.7573(2) 0.64549(6) 0.0268(5) Uani 1 1 d . . .
C107 C 0.66139(12) -0.6791(2) 0.67352(7) 0.0287(6) Uani 1 1 d . . .
H107 H 0.6724 -0.7243 0.6968 0.034 Uiso 1 1 d R . .
C210 C 0.72872(13) -0.5619(3) 0.85571(6) 0.0318(6) Uani 1 1 d . . .
H210 H 0.6835 -0.5393 0.8528 0.038 Uiso 1 1 d R . .
C111 C 0.47095(13) -1.0235(3) 0.65075(8) 0.0407(7) Uani 1 1 d . . .
H111 H 0.4446 -1.1008 0.6476 0.049 Uiso 1 1 d R . .
C216 C 0.70070(14) -0.3387(3) 0.79924(8) 0.0420(7) Uani 1 1 d . . .
H216A H 0.6656 -0.3491 0.8140 0.050 Uiso 1 1 d R . .
H216B H 0.6827 -0.2998 0.7765 0.050 Uiso 1 1 d R . .
H216C H 0.7348 -0.2805 0.8112 0.050 Uiso 1 1 d R . .
C101 C 0.62633(12) -0.4473(2) 0.67339(6) 0.0280(5) Uani 1 1 d . . .
C207 C 0.89767(12) -0.4165(2) 0.79769(6) 0.0270(5) Uani 1 1 d . . .
H207 H 0.8610 -0.3516 0.7978 0.032 Uiso 1 1 d R . .
C229 C 1.06263(15) -0.2899(3) 0.87547(7) 0.0448(7) Uani 1 1 d . . .
H229 H 1.0984 -0.2624 0.8922 0.054 Uiso 1 1 d R . .
B1 B 0.76662(14) -0.6268(3) 0.48792(7) 0.0263(6) Uani 1 1 d . . .
C212 C 0.82419(13) -0.6530(3) 0.89219(7) 0.0341(6) Uani 1 1 d . . .
H212 H 0.8432 -0.6906 0.9139 0.041 Uiso 1 1 d R . .
C115 C 0.57007(14) -0.8524(3) 0.56668(7) 0.0416(7) Uani 1 1 d . . .
H115A H 0.6083 -0.8956 0.5800 0.050 Uiso 1 1 d R . .
H115B H 0.5840 -0.8008 0.5473 0.050 Uiso 1 1 d R . .
H115C H 0.5383 -0.9197 0.5570 0.050 Uiso 1 1 d R . .
C230 C 1.07125(13) -0.3908(3) 0.85126(7) 0.0394(7) Uani 1 1 d . . .
H230 H 1.1130 -0.4314 0.8517 0.047 Uiso 1 1 d R . .
C117 C 0.56345(13) -0.8272(3) 0.72876(6) 0.0353(6) Uani 1 1 d . . .
H117 H 0.5835 -0.7374 0.7279 0.042 Uiso 1 1 d R . .
C122 C 0.40228(14) -0.3519(3) 0.62330(7) 0.0380(6) Uani 1 1 d . . .
H122 H 0.3907 -0.2818 0.6072 0.046 Uiso 1 1 d R . .
C130 C 0.74483(14) -0.7687(3) 0.59093(7) 0.0422(7) Uani 1 1 d . . .
H130 H 0.7582 -0.7254 0.5710 0.051 Uiso 1 1 d R . .
C112 C 0.49758(13) -0.9837(3) 0.68489(8) 0.0377(6) Uani 1 1 d . . .
H112 H 0.4896 -1.0354 0.7046 0.045 Uiso 1 1 d R . .
C201 C 0.90785(12) -0.5512(2) 0.74506(6) 0.0266(5) Uani 1 1 d . . .
C6 C 0.68896(13) -0.8526(2) 0.47809(6) 0.0312(6) Uani 1 1 d . . .
H6 H 0.7243 -0.9138 0.4800 0.037 Uiso 1 1 d R . .
C5 C 0.62368(13) -0.8978(3) 0.47100(6) 0.0337(6) Uani 1 1 d . . .
H5 H 0.6152 -0.9897 0.4680 0.040 Uiso 1 1 d R . .
C205 C 0.95293(15) -0.4666(3) 0.69290(7) 0.0439(7) Uani 1 1 d . . .
H205 H 0.9652 -0.4812 0.6701 0.053 Uiso 1 1 d R . .
C17 C 0.75287(14) -0.3398(3) 0.42192(7) 0.0371(6) Uani 1 1 d . . .
H17 H 0.7310 -0.4269 0.4247 0.045 Uiso 1 1 d R . .
C206 C 0.92634(13) -0.5710(3) 0.71073(7) 0.0353(6) Uani 1 1 d . . .
H206 H 0.9205 -0.6554 0.6999 0.042 Uiso 1 1 d R . .
C223 C 0.80839(14) -1.0600(3) 0.75943(7) 0.0383(7) Uani 1 1 d . . .
H223 H 0.7957 -1.1500 0.7565 0.046 Uiso 1 1 d R . .
C124 C 0.37081(14) -0.5245(3) 0.66128(7) 0.0390(7) Uani 1 1 d . . .
H124 H 0.3377 -0.5697 0.6716 0.047 Uiso 1 1 d R . .
C28 C 0.62530(13) -0.1858(3) 0.54061(7) 0.0335(6) Uani 1 1 d . . .
H28 H 0.6244 -0.0921 0.5391 0.040 Uiso 1 1 d R . .
C10 C 0.85243(13) -0.2062(3) 0.52418(8) 0.0408(7) Uani 1 1 d . . .
H10 H 0.8752 -0.1755 0.5459 0.049 Uiso 1 1 d R . .
C21 C 0.86008(14) -0.7806(3) 0.51700(7) 0.0385(7) Uani 1 1 d . . .
H21 H 0.8273 -0.8297 0.5266 0.046 Uiso 1 1 d R . .
C110 C 0.48345(13) -0.9492(3) 0.62139(8) 0.0371(6) Uani 1 1 d . . .
H110 H 0.4649 -0.9767 0.5985 0.044 Uiso 1 1 d R . .
C204 C 0.96182(15) -0.3403(3) 0.70859(7) 0.0442(7) Uani 1 1 d . . .
H204 H 0.9794 -0.2705 0.6961 0.053 Uiso 1 1 d R . .
C106 C 0.63701(14) -0.3088(3) 0.67851(7) 0.0375(6) Uani 1 1 d . . .
H106 H 0.6010 -0.2493 0.6751 0.045 Uiso 1 1 d R . .
C105 C 0.70107(15) -0.2606(3) 0.68846(7) 0.0411(7) Uani 1 1 d . . .
H105 H 0.7077 -0.1686 0.6924 0.049 Uiso 1 1 d R . .
C217 C 0.93653(13) -0.6762(3) 0.87129(7) 0.0377(6) Uani 1 1 d . . .
H217 H 0.9571 -0.6515 0.8499 0.045 Uiso 1 1 d R . .
C215 C 0.67762(14) -0.5719(3) 0.77461(7) 0.0429(7) Uani 1 1 d . . .
H215A H 0.6979 -0.6562 0.7696 0.051 Uiso 1 1 d R . .
H215B H 0.6572 -0.5320 0.7525 0.051 Uiso 1 1 d R . .
H215C H 0.6441 -0.5871 0.7902 0.051 Uiso 1 1 d R . .
C129 C 0.75348(14) -0.9064(3) 0.59493(8) 0.0411(7) Uani 1 1 d . . .
H129 H 0.7736 -0.9555 0.5781 0.049 Uiso 1 1 d R . .
C103 C 0.74608(13) -0.4848(3) 0.68770(7) 0.0371(6) Uani 1 1 d . . .
H103 H 0.7824 -0.5436 0.6908 0.045 Uiso 1 1 d R . .
C12 C 0.82320(13) -0.1764(3) 0.46094(8) 0.0392(7) Uani 1 1 d . . .
H12 H 0.8255 -0.1257 0.4403 0.047 Uiso 1 1 d R . .
C11 C 0.85543(14) -0.1319(3) 0.49336(9) 0.0444(7) Uani 1 1 d . . .
H11 H 0.8794 -0.0515 0.4945 0.053 Uiso 1 1 d R . .
C15 C 0.88349(14) -0.4631(3) 0.57213(8) 0.0465(7) Uani 1 1 d . . .
H15A H 0.8968 -0.5229 0.5542 0.056 Uiso 1 1 d R . .
H15B H 0.8809 -0.5124 0.5940 0.056 Uiso 1 1 d R . .
H15C H 0.9158 -0.3919 0.5767 0.056 Uiso 1 1 d R . .
C224 C 0.79631(15) -0.9901(3) 0.78871(8) 0.0456(8) Uani 1 1 d . . .
H224 H 0.7747 -1.0322 0.8061 0.055 Uiso 1 1 d R . .
C104 C 0.75509(14) -0.3470(3) 0.69263(7) 0.0410(7) Uani 1 1 d . . .
H104 H 0.7980 -0.3124 0.6988 0.049 Uiso 1 1 d R . .
C25 C 0.89209(13) -0.6066(3) 0.47874(8) 0.0422(7) Uani 1 1 d . . .
H25 H 0.8813 -0.5344 0.4632 0.051 Uiso 1 1 d R . .
C203 C 0.94450(13) -0.3168(3) 0.74259(7) 0.0374(6) Uani 1 1 d . . .
H203 H 0.9508 -0.2323 0.7533 0.045 Uiso 1 1 d R . .
C30 C 0.60932(14) -0.3885(3) 0.57258(7) 0.0393(7) Uani 1 1 d . . .
H30 H 0.5976 -0.4320 0.5928 0.047 Uiso 1 1 d R . .
C228 C 1.00109(16) -0.2300(3) 0.87483(7) 0.0469(8) Uani 1 1 d . . .
H228 H 0.9952 -0.1621 0.8913 0.056 Uiso 1 1 d R . .
C211 C 0.75722(13) -0.6194(3) 0.88761(7) 0.0346(6) Uani 1 1 d . . .
H211 H 0.7314 -0.6354 0.9060 0.041 Uiso 1 1 d R . .
C225 C 0.81587(16) -0.8568(3) 0.79335(7) 0.0465(8) Uani 1 1 d . . .
H225 H 0.8062 -0.8110 0.8137 0.056 Uiso 1 1 d R . .
C29 C 0.60762(13) -0.2491(3) 0.57079(7) 0.0373(6) Uani 1 1 d . . .
H29 H 0.5946 -0.1988 0.5896 0.045 Uiso 1 1 d R . .
C123 C 0.35349(14) -0.4192(3) 0.63817(8) 0.0407(7) Uani 1 1 d . . .
H123 H 0.3088 -0.3941 0.6326 0.049 Uiso 1 1 d R . .
C19 C 0.69875(16) -0.2373(3) 0.40740(8) 0.0550(8) Uani 1 1 d . . .
H19A H 0.6693 -0.2227 0.4252 0.066 Uiso 1 1 d R . .
H19B H 0.6736 -0.2716 0.3857 0.066 Uiso 1 1 d R . .
H19C H 0.7195 -0.1536 0.4023 0.066 Uiso 1 1 d R . .
C118 C 0.61850(15) -0.9241(3) 0.74488(8) 0.0476(8) Uani 1 1 d . . .
H118A H 0.6010 -1.0143 0.7445 0.057 Uiso 1 1 d R . .
H118B H 0.6340 -0.8985 0.7693 0.057 Uiso 1 1 d R . .
H118C H 0.6551 -0.9206 0.7309 0.057 Uiso 1 1 d R . .
C116 C 0.47541(15) -0.6934(3) 0.57113(7) 0.0468(7) Uani 1 1 d . . .
H116A H 0.4436 -0.7619 0.5624 0.056 Uiso 1 1 d R . .
H116B H 0.4878 -0.6430 0.5511 0.056 Uiso 1 1 d R . .
H116C H 0.4557 -0.6338 0.5870 0.056 Uiso 1 1 d R . .
C24 C 0.95810(15) -0.6467(4) 0.48649(10) 0.0594(10) Uani 1 1 d . . .
H24 H 0.9909 -0.6039 0.4753 0.071 Uiso 1 1 d R . .
C218 C 0.94204(16) -0.8297(3) 0.87577(8) 0.0522(8) Uani 1 1 d . . .
H218A H 0.9237 -0.8565 0.8971 0.063 Uiso 1 1 d R . .
H218B H 0.9883 -0.8557 0.8779 0.063 Uiso 1 1 d R . .
H218C H 0.9177 -0.8730 0.8551 0.063 Uiso 1 1 d R . .
C119 C 0.50878(16) -0.8187(3) 0.75328(8) 0.0495(8) Uani 1 1 d . . .
H119A H 0.4756 -0.7541 0.7437 0.059 Uiso 1 1 d R . .
H119B H 0.5284 -0.7910 0.7769 0.059 Uiso 1 1 d R . .
H119C H 0.4882 -0.9056 0.7547 0.059 Uiso 1 1 d R . .
C22 C 0.92711(16) -0.8162(3) 0.52588(9) 0.0554(9) Uani 1 1 d . . .
H22 H 0.9390 -0.8857 0.5422 0.067 Uiso 1 1 d R . .
C219 C 0.97539(15) -0.6049(3) 0.90358(8) 0.0520(8) Uani 1 1 d . . .
H219A H 0.9712 -0.5090 0.9004 0.062 Uiso 1 1 d R . .
H219B H 1.0218 -0.6300 0.9056 0.062 Uiso 1 1 d R . .
H219C H 0.9577 -0.6307 0.9251 0.062 Uiso 1 1 d R . .
C16 C 0.79168(15) -0.3145(3) 0.58808(7) 0.0481(8) Uani 1 1 d . . .
H16A H 0.8240 -0.2446 0.5947 0.058 Uiso 1 1 d R . .
H16B H 0.7873 -0.3694 0.6088 0.058 Uiso 1 1 d R . .
H16C H 0.7491 -0.2746 0.5794 0.058 Uiso 1 1 d R . .
C221 C 0.8596(2) -0.8633(3) 0.73922(9) 0.0724(12) Uani 1 1 d . . .
H221 H 0.8814 -0.8227 0.7216 0.087 Uiso 1 1 d R . .
C222 C 0.8395(2) -0.9959(3) 0.73438(9) 0.0818(14) Uani 1 1 d . . .
H222 H 0.8473 -1.0417 0.7137 0.098 Uiso 1 1 d R . .
C23 C 0.97570(16) -0.7491(4) 0.51051(11) 0.0653(11) Uani 1 1 d . . .
H23 H 1.0205 -0.7731 0.5164 0.078 Uiso 1 1 d R . .
C18 C 0.80243(18) -0.3578(4) 0.39509(9) 0.0722(11) Uani 1 1 d . . .
H18A H 0.8254 -0.2741 0.3925 0.087 Uiso 1 1 d R . .
H18B H 0.7790 -0.3845 0.3721 0.087 Uiso 1 1 d R . .
H18C H 0.8344 -0.4262 0.4037 0.087 Uiso 1 1 d 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
N2 B2 1.405(3) . ?
N2 C108 1.439(3) . ?
N2 C107 1.484(3) . ?
C208 C213 1.400(3) . ?
C208 C209 1.407(3) . ?
C208 N3 1.444(3) . ?
N1 B1 1.403(3) . ?
N1 C8 1.439(3) . ?
N1 C7 1.490(3) . ?
C108 C109 1.399(3) . ?
C108 C113 1.401(3) . ?
C8 C9 1.403(3) . ?
C8 C13 1.404(3) . ?
C113 C112 1.396(3) . ?
C113 C117 1.516(3) . ?
N3 B3 1.409(3) . ?
N3 C207 1.488(3) . ?
C220 C221 1.368(4) . ?
C220 C225 1.382(3) . ?
C220 B3 1.571(4) . ?
C209 C210 1.390(3) . ?
C209 C214 1.516(3) . ?
C1 C6 1.398(3) . ?
C1 C2 1.401(3) . ?
C1 B1 1.559(4) . ?
C3 C4 1.385(3) . ?
C3 C2 1.385(3) . ?
C3 H3 0.9299 . ?
C213 C212 1.394(3) . ?
C213 C217 1.515(3) . ?
C202 C203 1.388(3) . ?
C202 C201 1.398(3) . ?
C202 C207 1.510(3) . ?
C231 C230 1.379(4) . ?
C231 C226 1.387(3) . ?
C231 H231 0.9301 . ?
C26 C31 1.385(3) . ?
C26 C27 1.390(3) . ?
C26 C7 1.518(3) . ?
C109 C110 1.393(3) . ?
C109 C114 1.515(3) . ?
C120 C125 1.395(3) . ?
C120 C121 1.398(3) . ?
C120 B2 1.555(4) . ?
C9 C10 1.394(4) . ?
C9 C14 1.513(3) . ?
C2 C7 1.514(3) . ?
C102 C103 1.383(3) . ?
C102 C101 1.390(3) . ?
C102 C107 1.512(3) . ?
C131 C130 1.379(4) . ?
C131 C126 1.381(3) . ?
C131 H131 0.9301 . ?
C14 C15 1.530(4) . ?
C14 C16 1.532(4) . ?
C14 H14 0.9800 . ?
C7 H7 0.9799 . ?
C114 C115 1.525(3) . ?
C114 C116 1.526(4) . ?
C114 H114 0.9800 . ?
C226 C227 1.383(3) . ?
C226 C207 1.516(3) . ?
C227 C228 1.394(4) . ?
C227 H227 0.9300 . ?
C13 C12 1.390(3) . ?
C13 C17 1.512(4) . ?
C125 C124 1.379(4) . ?
C125 H125 0.9301 . ?
C214 C215 1.524(3) . ?
C214 C216 1.529(4) . ?
C214 H214 0.9801 . ?
C27 C28 1.383(3) . ?
C27 H27 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C128 C129 1.374(4) . ?
C128 C127 1.382(4) . ?
C128 H128 0.9300 . ?
C121 C122 1.388(4) . ?
C121 H121 0.9299 . ?
C31 C30 1.381(3) . ?
C31 H31 0.9299 . ?
C20 C21 1.396(4) . ?
C20 C25 1.400(4) . ?
C20 B1 1.555(4) . ?
C127 C126 1.386(3) . ?
C127 H127 0.9300 . ?
B3 C201 1.574(3) . ?
B2 C101 1.559(4) . ?
C126 C107 1.528(3) . ?
C107 H107 0.9800 . ?
C210 C211 1.377(3) . ?
C210 H210 0.9300 . ?
C111 C110 1.374(4) . ?
C111 C112 1.376(4) . ?
C111 H111 0.9301 . ?
C216 H216A 0.9601 . ?
C216 H216B 0.9600 . ?
C216 H216C 0.9600 . ?
C101 C106 1.398(3) . ?
C207 H207 0.9800 . ?
C229 C228 1.372(4) . ?
C229 C230 1.376(4) . ?
C229 H229 0.9300 . ?
C212 C211 1.377(4) . ?
C212 H212 0.9298 . ?
C115 H115A 0.9599 . ?
C115 H115B 0.9599 . ?
C115 H115C 0.9600 . ?
C230 H230 0.9299 . ?
C117 C119 1.527(4) . ?
C117 C118 1.529(4) . ?
C117 H117 0.9800 . ?
C122 C123 1.366(4) . ?
C122 H122 0.9300 . ?
C130 C129 1.381(4) . ?
C130 H130 0.9300 . ?
C112 H112 0.9300 . ?
C201 C206 1.399(3) . ?
C6 C5 1.381(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C205 C206 1.378(4) . ?
C205 C204 1.383(4) . ?
C205 H205 0.9301 . ?
C17 C18 1.518(4) . ?
C17 C19 1.535(4) . ?
C17 H17 0.9800 . ?
C206 H206 0.9301 . ?
C223 C224 1.346(4) . ?
C223 C222 1.354(4) . ?
C223 H223 0.9300 . ?
C124 C123 1.370(4) . ?
C124 H124 0.9300 . ?
C28 C29 1.380(4) . ?
C28 H28 0.9301 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9301 . ?
C21 C22 1.392(4) . ?
C21 H21 0.9302 . ?
C110 H110 0.9299 . ?
C204 C203 1.384(4) . ?
C204 H204 0.9301 . ?
C106 C105 1.380(4) . ?
C106 H106 0.9301 . ?
C105 C104 1.377(4) . ?
C105 H105 0.9300 . ?
C217 C219 1.523(4) . ?
C217 C218 1.532(4) . ?
C217 H217 0.9800 . ?
C215 H215A 0.9600 . ?
C215 H215B 0.9602 . ?
C215 H215C 0.9600 . ?
C129 H129 0.9300 . ?
C103 C104 1.387(4) . ?
C103 H103 0.9300 . ?
C12 C11 1.370(4) . ?
C12 H12 0.9298 . ?
C11 H11 0.9299 . ?
C15 H15A 0.9599 . ?
C15 H15B 0.9601 . ?
C15 H15C 0.9600 . ?
C224 C225 1.383(4) . ?
C224 H224 0.9299 . ?
C104 H104 0.9300 . ?
C25 C24 1.381(4) . ?
C25 H25 0.9300 . ?
C203 H203 0.9300 . ?
C30 C29 1.383(4) . ?
C30 H30 0.9300 . ?
C228 H228 0.9301 . ?
C211 H211 0.9301 . ?
C225 H225 0.9301 . ?
C29 H29 0.9297 . ?
C123 H123 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9599 . ?
C19 H19C 0.9599 . ?
C118 H118A 0.9601 . ?
C118 H118B 0.9602 . ?
C118 H118C 0.9597 . ?
C116 H116A 0.9601 . ?
C116 H116B 0.9601 . ?
C116 H116C 0.9598 . ?
C24 C23 1.371(5) . ?
C24 H24 0.9301 . ?
C218 H218A 0.9602 . ?
C218 H218B 0.9599 . ?
C218 H218C 0.9599 . ?
C119 H119A 0.9600 . ?
C119 H119B 0.9599 . ?
C119 H119C 0.9600 . ?
C22 C23 1.372(5) . ?
C22 H22 0.9301 . ?
C219 H219A 0.9600 . ?
C219 H219B 0.9599 . ?
C219 H219C 0.9600 . ?
C16 H16A 0.9599 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C221 C222 1.380(4) . ?
C221 H221 0.9303 . ?
C222 H222 0.9302 . ?
C23 H23 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9601 . ?

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
B2 N2 C108 127.4(2) . . ?
B2 N2 C107 113.26(19) . . ?
C108 N2 C107 119.30(18) . . ?
C213 C208 C209 121.1(2) . . ?
C213 C208 N3 120.8(2) . . ?
C209 C208 N3 118.1(2) . . ?
B1 N1 C8 129.2(2) . . ?
B1 N1 C7 113.03(19) . . ?
C8 N1 C7 117.75(18) . . ?
C109 C108 C113 121.6(2) . . ?
C109 C108 N2 119.3(2) . . ?
C113 C108 N2 119.1(2) . . ?
C9 C8 C13 121.4(2) . . ?
C9 C8 N1 120.1(2) . . ?
C13 C8 N1 118.5(2) . . ?
C112 C113 C108 118.0(2) . . ?
C112 C113 C117 118.7(2) . . ?
C108 C113 C117 123.4(2) . . ?
B3 N3 C208 128.6(2) . . ?
B3 N3 C207 113.13(19) . . ?
C208 N3 C207 116.52(18) . . ?
C221 C220 C225 114.8(2) . . ?
C221 C220 B3 120.1(2) . . ?
C225 C220 B3 125.2(2) . . ?
C210 C209 C208 118.2(2) . . ?
C210 C209 C214 118.6(2) . . ?
C208 C209 C214 123.2(2) . . ?
C6 C1 C2 118.5(2) . . ?
C6 C1 B1 134.3(2) . . ?
C2 C1 B1 107.0(2) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.7 . . ?
C212 C213 C208 118.2(2) . . ?
C212 C213 C217 118.6(2) . . ?
C208 C213 C217 123.2(2) . . ?
C203 C202 C201 122.5(2) . . ?
C203 C202 C207 125.5(2) . . ?
C201 C202 C207 112.0(2) . . ?
C230 C231 C226 121.0(2) . . ?
C230 C231 H231 119.4 . . ?
C226 C231 H231 119.6 . . ?
C31 C26 C27 118.4(2) . . ?
C31 C26 C7 122.3(2) . . ?
C27 C26 C7 119.2(2) . . ?
C110 C109 C108 117.8(2) . . ?
C110 C109 C114 119.1(2) . . ?
C108 C109 C114 123.0(2) . . ?
C125 C120 C121 116.3(2) . . ?
C125 C120 B2 122.7(2) . . ?
C121 C120 B2 120.9(2) . . ?
C10 C9 C8 117.4(2) . . ?
C10 C9 C14 119.1(2) . . ?
C8 C9 C14 123.5(2) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 C7 126.7(2) . . ?
C1 C2 C7 111.5(2) . . ?
C103 C102 C101 122.3(2) . . ?
C103 C102 C107 125.9(2) . . ?
C101 C102 C107 111.7(2) . . ?
C130 C131 C126 120.9(2) . . ?
C130 C131 H131 119.5 . . ?
C126 C131 H131 119.6 . . ?
C9 C14 C15 111.3(2) . . ?
C9 C14 C16 112.3(2) . . ?
C15 C14 C16 109.3(2) . . ?
C9 C14 H14 107.9 . . ?
C15 C14 H14 107.8 . . ?
C16 C14 H14 108.0 . . ?
N1 C7 C2 102.75(18) . . ?
N1 C7 C26 112.09(18) . . ?
C2 C7 C26 116.08(19) . . ?
N1 C7 H7 108.5 . . ?
C2 C7 H7 108.5 . . ?
C26 C7 H7 108.5 . . ?
C109 C114 C115 111.2(2) . . ?
C109 C114 C116 112.8(2) . . ?
C115 C114 C116 109.8(2) . . ?
C109 C114 H114 107.6 . . ?
C115 C114 H114 107.6 . . ?
C116 C114 H114 107.7 . . ?
C227 C226 C231 118.4(2) . . ?
C227 C226 C207 120.7(2) . . ?
C231 C226 C207 120.9(2) . . ?
C226 C227 C228 120.5(3) . . ?
C226 C227 H227 119.8 . . ?
C228 C227 H227 119.7 . . ?
C12 C13 C8 118.5(2) . . ?
C12 C13 C17 118.2(2) . . ?
C8 C13 C17 123.3(2) . . ?
C124 C125 C120 121.5(2) . . ?
C124 C125 H125 119.2 . . ?
C120 C125 H125 119.3 . . ?
C209 C214 C215 111.3(2) . . ?
C209 C214 C216 111.8(2) . . ?
C215 C214 C216 110.5(2) . . ?
C209 C214 H214 107.8 . . ?
C215 C214 H214 107.7 . . ?
C216 C214 H214 107.6 . . ?
C28 C27 C26 120.9(2) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C129 C128 C127 119.9(2) . . ?
C129 C128 H128 120.0 . . ?
C127 C128 H128 120.1 . . ?
C122 C121 C120 121.8(2) . . ?
C122 C121 H121 119.1 . . ?
C120 C121 H121 119.1 . . ?
C30 C31 C26 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C26 C31 H31 119.7 . . ?
C21 C20 C25 117.0(2) . . ?
C21 C20 B1 119.5(2) . . ?
C25 C20 B1 123.4(2) . . ?
C128 C127 C126 121.4(2) . . ?
C128 C127 H127 119.3 . . ?
C126 C127 H127 119.3 . . ?
N3 B3 C220 126.3(2) . . ?
N3 B3 C201 105.2(2) . . ?
C220 B3 C201 128.5(2) . . ?
N2 B2 C120 125.4(2) . . ?
N2 B2 C101 105.2(2) . . ?
C120 B2 C101 129.4(2) . . ?
C131 C126 C127 118.0(2) . . ?
C131 C126 C107 122.2(2) . . ?
C127 C126 C107 119.8(2) . . ?
N2 C107 C102 102.62(18) . . ?
N2 C107 C126 113.72(19) . . ?
C102 C107 C126 115.4(2) . . ?
N2 C107 H107 108.3 . . ?
C102 C107 H107 108.3 . . ?
C126 C107 H107 108.2 . . ?
C211 C210 C209 121.4(2) . . ?
C211 C210 H210 119.3 . . ?
C209 C210 H210 119.3 . . ?
C110 C111 C112 119.9(2) . . ?
C110 C111 H111 120.1 . . ?
C112 C111 H111 120.0 . . ?
C214 C216 H216A 109.3 . . ?
C214 C216 H216B 109.6 . . ?
H216A C216 H216B 109.5 . . ?
C214 C216 H216C 109.4 . . ?
H216A C216 H216C 109.5 . . ?
H216B C216 H216C 109.5 . . ?
C102 C101 C106 118.2(2) . . ?
C102 C101 B2 107.2(2) . . ?
C106 C101 B2 134.5(2) . . ?
N3 C207 C202 102.93(18) . . ?
N3 C207 C226 114.72(19) . . ?
C202 C207 C226 112.08(19) . . ?
N3 C207 H207 109.1 . . ?
C202 C207 H207 109.0 . . ?
C226 C207 H207 108.8 . . ?
C228 C229 C230 119.8(3) . . ?
C228 C229 H229 120.1 . . ?
C230 C229 H229 120.1 . . ?
N1 B1 C20 125.1(2) . . ?
N1 B1 C1 105.6(2) . . ?
C20 B1 C1 129.2(2) . . ?
C211 C212 C213 121.4(2) . . ?
C211 C212 H212 119.2 . . ?
C213 C212 H212 119.4 . . ?
C114 C115 H115A 109.4 . . ?
C114 C115 H115B 109.6 . . ?
H115A C115 H115B 109.5 . . ?
C114 C115 H115C 109.5 . . ?
H115A C115 H115C 109.5 . . ?
H115B C115 H115C 109.5 . . ?
C229 C230 C231 120.2(3) . . ?
C229 C230 H230 119.8 . . ?
C231 C230 H230 120.0 . . ?
C113 C117 C119 112.8(2) . . ?
C113 C117 C118 111.0(2) . . ?
C119 C117 C118 109.9(2) . . ?
C113 C117 H117 107.7 . . ?
C119 C117 H117 107.7 . . ?
C118 C117 H117 107.6 . . ?
C123 C122 C121 120.1(3) . . ?
C123 C122 H122 119.9 . . ?
C121 C122 H122 120.1 . . ?
C131 C130 C129 120.5(3) . . ?
C131 C130 H130 119.7 . . ?
C129 C130 H130 119.8 . . ?
C111 C112 C113 121.1(2) . . ?
C111 C112 H112 119.5 . . ?
C113 C112 H112 119.4 . . ?
C202 C201 C206 117.5(2) . . ?
C202 C201 B3 106.6(2) . . ?
C206 C201 B3 135.8(2) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.2 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.6 . . ?
C206 C205 C204 120.7(2) . . ?
C206 C205 H205 119.7 . . ?
C204 C205 H205 119.7 . . ?
C13 C17 C18 112.0(2) . . ?
C13 C17 C19 110.2(2) . . ?
C18 C17 C19 110.0(3) . . ?
C13 C17 H17 108.2 . . ?
C18 C17 H17 108.1 . . ?
C19 C17 H17 108.1 . . ?
C205 C206 C201 120.5(2) . . ?
C205 C206 H206 119.8 . . ?
C201 C206 H206 119.7 . . ?
C224 C223 C222 118.2(3) . . ?
C224 C223 H223 120.9 . . ?
C222 C223 H223 120.9 . . ?
C123 C124 C125 120.8(3) . . ?
C123 C124 H124 119.6 . . ?
C125 C124 H124 119.6 . . ?
C29 C28 C27 120.3(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.9 . . ?
C11 C10 C9 121.7(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.1 . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C111 C110 C109 121.5(2) . . ?
C111 C110 H110 119.1 . . ?
C109 C110 H110 119.3 . . ?
C205 C204 C203 120.6(2) . . ?
C205 C204 H204 119.7 . . ?
C203 C204 H204 119.7 . . ?
C105 C106 C101 119.9(3) . . ?
C105 C106 H106 120.1 . . ?
C101 C106 H106 120.0 . . ?
C104 C105 C106 120.7(2) . . ?
C104 C105 H105 119.8 . . ?
C106 C105 H105 119.4 . . ?
C213 C217 C219 111.8(2) . . ?
C213 C217 C218 111.1(2) . . ?
C219 C217 C218 110.6(2) . . ?
C213 C217 H217 107.7 . . ?
C219 C217 H217 107.7 . . ?
C218 C217 H217 107.8 . . ?
C214 C215 H215A 109.6 . . ?
C214 C215 H215B 109.4 . . ?
H215A C215 H215B 109.4 . . ?
C214 C215 H215C 109.5 . . ?
H215A C215 H215C 109.5 . . ?
H215B C215 H215C 109.5 . . ?
C128 C129 C130 119.4(3) . . ?
C128 C129 H129 120.4 . . ?
C130 C129 H129 120.2 . . ?
C102 C103 C104 118.2(3) . . ?
C102 C103 H103 120.9 . . ?
C104 C103 H103 120.9 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 119.9 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C223 C224 C225 121.0(3) . . ?
C223 C224 H224 119.5 . . ?
C225 C224 H224 119.6 . . ?
C105 C104 C103 120.7(3) . . ?
C105 C104 H104 119.6 . . ?
C103 C104 H104 119.7 . . ?
C24 C25 C20 121.2(3) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
C204 C203 C202 118.3(2) . . ?
C204 C203 H203 120.8 . . ?
C202 C203 H203 120.9 . . ?
C31 C30 C29 120.7(2) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.7 . . ?
C229 C228 C227 120.1(3) . . ?
C229 C228 H228 119.8 . . ?
C227 C228 H228 120.1 . . ?
C210 C211 C212 119.7(2) . . ?
C210 C211 H211 120.2 . . ?
C212 C211 H211 120.1 . . ?
C220 C225 C224 122.4(2) . . ?
C220 C225 H225 118.9 . . ?
C224 C225 H225 118.8 . . ?
C28 C29 C30 119.1(2) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.4 . . ?
C122 C123 C124 119.5(3) . . ?
C122 C123 H123 120.3 . . ?
C124 C123 H123 120.2 . . ?
C17 C19 H19A 109.3 . . ?
C17 C19 H19B 109.6 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C117 C118 H118A 109.5 . . ?
C117 C118 H118B 109.6 . . ?
H118A C118 H118B 109.5 . . ?
C117 C118 H118C 109.3 . . ?
H118A C118 H118C 109.5 . . ?
H118B C118 H118C 109.5 . . ?
C114 C116 H116A 109.6 . . ?
C114 C116 H116B 109.5 . . ?
H116A C116 H116B 109.5 . . ?
C114 C116 H116C 109.3 . . ?
H116A C116 H116C 109.5 . . ?
H116B C116 H116C 109.5 . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.8 . . ?
C217 C218 H218A 109.6 . . ?
C217 C218 H218B 109.3 . . ?
H218A C218 H218B 109.5 . . ?
C217 C218 H218C 109.5 . . ?
H218A C218 H218C 109.5 . . ?
H218B C218 H218C 109.5 . . ?
C117 C119 H119A 109.6 . . ?
C117 C119 H119B 109.3 . . ?
H119A C119 H119B 109.5 . . ?
C117 C119 H119C 109.5 . . ?
H119A C119 H119C 109.5 . . ?
H119B C119 H119C 109.5 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C217 C219 H219A 109.4 . . ?
C217 C219 H219B 109.4 . . ?
H219A C219 H219B 109.5 . . ?
C217 C219 H219C 109.5 . . ?
H219A C219 H219C 109.5 . . ?
H219B C219 H219C 109.5 . . ?
C14 C16 H16A 109.7 . . ?
C14 C16 H16B 109.3 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C220 C221 C222 122.9(3) . . ?
C220 C221 H221 118.6 . . ?
C222 C221 H221 118.5 . . ?
C223 C222 C221 120.7(3) . . ?
C223 C222 H222 119.6 . . ?
C221 C222 H222 119.7 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.3 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.75
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 999428'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 B N'
_chemical_formula_sum            'C26 H30 B N'
_chemical_formula_weight         367.32

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.4121(8)
_cell_length_b                   12.0880(6)
_cell_length_c                   17.2750(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.555(6)
_cell_angle_gamma                90
_cell_volume                     2130.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    21707
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.065
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.120
-1 0 0 0.075
0 0 -1 0.159
0 0 1 0.223
0 1 0 0.055
0 -1 0 0.102
0 -1 1 0.171
1 0 1 0.154
-1 0 1 0.166
1 -1 0 0.121
-1 1 0 0.061


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21672
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4852
_reflns_number_gt                3721
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0355P)²+1.0721P] 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         4852
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.75668(12) 0.25164(10) 0.26287(7) 0.0190(3) Uani 1 1 d . . .
C9 C 0.71995(15) 0.33187(13) 0.13007(9) 0.0230(3) Uani 1 1 d . . .
C3 C 0.62205(16) 0.00659(13) 0.34732(9) 0.0241(3) Uani 1 1 d . . .
H3 H 0.5314 0.0030 0.3313 0.029 Uiso 1 1 d R . .
C17 C 0.77863(16) 0.47453(14) 0.33423(10) 0.0266(4) Uani 1 1 d . . .
H17 H 0.7874 0.4026 0.3609 0.032 Uiso 1 1 d R . .
C11 C 0.71952(17) 0.53021(14) 0.11382(11) 0.0300(4) Uani 1 1 d . . .
H11 H 0.7107 0.5917 0.0808 0.036 Uiso 1 1 d R . .
C14 C 0.71545(17) 0.21793(14) 0.09200(9) 0.0266(4) Uani 1 1 d . . .
H14 H 0.7364 0.1628 0.1343 0.032 Uiso 1 1 d R . .
C13 C 0.75603(15) 0.45390(13) 0.24574(9) 0.0222(3) Uani 1 1 d . . .
C26 C 0.53609(16) 0.25563(14) 0.29846(11) 0.0288(4) Uani 1 1 d . . .
H26A H 0.5738 0.2861 0.3492 0.035 Uiso 1 1 d R . .
H26B H 0.4628 0.2097 0.3030 0.035 Uiso 1 1 d R . .
H26C H 0.5071 0.3146 0.2619 0.035 Uiso 1 1 d R . .
C20 C 1.00854(15) 0.26680(12) 0.32717(9) 0.0208(3) Uani 1 1 d . . .
C2 C 0.69251(15) 0.09352(13) 0.32360(9) 0.0203(3) Uani 1 1 d . . .
C1 C 0.82823(16) 0.10227(13) 0.34906(9) 0.0213(3) Uani 1 1 d . . .
C25 C 1.07726(17) 0.27164(14) 0.40549(10) 0.0267(4) Uani 1 1 d . . .
H25 H 1.0414 0.2385 0.4449 0.032 Uiso 1 1 d R . .
C7 C 0.63839(15) 0.18693(13) 0.26870(9) 0.0210(3) Uani 1 1 d . . .
H7 H 0.5999 0.1565 0.2166 0.025 Uiso 1 1 d R . .
C8 C 0.74296(14) 0.34719(12) 0.21273(9) 0.0199(3) Uani 1 1 d . . .
C4 C 0.69040(18) -0.07459(14) 0.39540(10) 0.0286(4) Uani 1 1 d . . .
H4 H 0.6449 -0.1335 0.4117 0.034 Uiso 1 1 d R . .
B1 B 0.87122(18) 0.20981(15) 0.31099(10) 0.0207(4) Uani 1 1 d . . .
C19 C 0.66162(19) 0.53474(16) 0.35623(11) 0.0353(4) Uani 1 1 d . . .
H19A H 0.6565 0.6085 0.3353 0.042 Uiso 1 1 d R . .
H19B H 0.6725 0.5378 0.4127 0.042 Uiso 1 1 d R . .
H19C H 0.5824 0.4955 0.3345 0.042 Uiso 1 1 d R . .
C21 C 1.06626(16) 0.31774(14) 0.27011(10) 0.0253(3) Uani 1 1 d . . .
H21 H 1.0224 0.3173 0.2176 0.030 Uiso 1 1 d R . .
C24 C 1.19731(17) 0.32439(15) 0.42594(11) 0.0328(4) Uani 1 1 d . . .
H24 H 1.2403 0.3276 0.4786 0.039 Uiso 1 1 d R . .
C22 C 1.18742(17) 0.36905(15) 0.29004(11) 0.0317(4) Uani 1 1 d . . .
H22 H 1.2248 0.4009 0.2508 0.038 Uiso 1 1 d R . .
C6 C 0.89522(17) 0.01918(14) 0.39704(10) 0.0267(4) Uani 1 1 d . . .
H6 H 0.9857 0.0230 0.4139 0.032 Uiso 1 1 d R . .
C12 C 0.74596(16) 0.54414(14) 0.19462(11) 0.0282(4) Uani 1 1 d . . .
H12 H 0.7573 0.6152 0.2155 0.034 Uiso 1 1 d R . .
C23 C 1.25284(17) 0.37274(15) 0.36796(12) 0.0331(4) Uani 1 1 d . . .
H23 H 1.3340 0.4075 0.3813 0.040 Uiso 1 1 d R . .
C10 C 0.70614(17) 0.42528(15) 0.08191(10) 0.0291(4) Uani 1 1 d . . .
H10 H 0.6879 0.4167 0.0273 0.035 Uiso 1 1 d R . .
C15 C 0.8171(2) 0.20796(17) 0.03990(11) 0.0374(4) Uani 1 1 d . . .
H15A H 0.7943 0.2569 -0.0045 0.045 Uiso 1 1 d R . .
H15B H 0.8189 0.1332 0.0215 0.045 Uiso 1 1 d R . .
H15C H 0.9020 0.2275 0.0699 0.045 Uiso 1 1 d R . .
C5 C 0.82542(18) -0.06915(14) 0.41936(10) 0.0300(4) Uani 1 1 d . . .
H5 H 0.8696 -0.1253 0.4506 0.036 Uiso 1 1 d R . .
C18 C 0.90417(19) 0.54039(16) 0.36439(12) 0.0372(4) Uani 1 1 d . . .
H18A H 0.9770 0.5032 0.3495 0.045 Uiso 1 1 d R . .
H18B H 0.9187 0.5461 0.4209 0.045 Uiso 1 1 d R . .
H18C H 0.8956 0.6131 0.3417 0.045 Uiso 1 1 d R . .
C16 C 0.57845(19) 0.19195(17) 0.04392(11) 0.0366(4) Uani 1 1 d . . .
H16A H 0.5556 0.2452 0.0022 0.044 Uiso 1 1 d R . .
H16B H 0.5159 0.1954 0.0778 0.044 Uiso 1 1 d R . .
H16C H 0.5779 0.1191 0.0217 0.044 Uiso 1 1 d 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
N1 B1 1.404(2) . ?
N1 C8 1.4335(19) . ?
N1 C7 1.4794(19) . ?
C9 C10 1.393(2) . ?
C9 C8 1.412(2) . ?
C9 C14 1.523(2) . ?
C3 C4 1.387(2) . ?
C3 C2 1.390(2) . ?
C3 H3 0.9300 . ?
C17 C13 1.520(2) . ?
C17 C18 1.530(2) . ?
C17 C19 1.531(2) . ?
C17 H17 0.9800 . ?
C11 C12 1.378(3) . ?
C11 C10 1.379(3) . ?
C11 H11 0.9300 . ?
C14 C15 1.525(3) . ?
C14 C16 1.532(2) . ?
C14 H14 0.9799 . ?
C13 C12 1.394(2) . ?
C13 C8 1.406(2) . ?
C26 C7 1.519(2) . ?
C26 H26A 0.9601 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C20 C21 1.396(2) . ?
C20 C25 1.399(2) . ?
C20 B1 1.561(2) . ?
C2 C1 1.397(2) . ?
C2 C7 1.509(2) . ?
C1 C6 1.397(2) . ?
C1 B1 1.562(2) . ?
C25 C24 1.385(2) . ?
C25 H25 0.9300 . ?
C7 H7 0.9799 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9299 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.386(2) . ?
C21 H21 0.9300 . ?
C24 C23 1.382(3) . ?
C24 H24 0.9299 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9299 . ?
C6 C5 1.389(2) . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C23 H23 0.9300 . ?
C10 H10 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9599 . ?
C15 H15C 0.9600 . ?
C5 H5 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9601 . ?
C18 H18C 0.9599 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
B1 N1 C8 128.16(13) . . ?
B1 N1 C7 112.91(13) . . ?
C8 N1 C7 118.92(12) . . ?
C10 C9 C8 118.29(15) . . ?
C10 C9 C14 119.00(15) . . ?
C8 C9 C14 122.66(14) . . ?
C4 C3 C2 118.29(15) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.8 . . ?
C13 C17 C18 112.17(15) . . ?
C13 C17 C19 110.92(14) . . ?
C18 C17 C19 109.64(14) . . ?
C13 C17 H17 108.0 . . ?
C18 C17 H17 108.0 . . ?
C19 C17 H17 108.0 . . ?
C12 C11 C10 120.07(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C9 C14 C15 111.18(15) . . ?
C9 C14 C16 111.36(14) . . ?
C15 C14 C16 110.15(14) . . ?
C9 C14 H14 108.1 . . ?
C15 C14 H14 108.0 . . ?
C16 C14 H14 108.0 . . ?
C12 C13 C8 118.18(15) . . ?
C12 C13 C17 119.04(15) . . ?
C8 C13 C17 122.78(14) . . ?
C7 C26 H26A 109.5 . . ?
C7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C7 C26 H26C 109.4 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C20 C25 117.07(15) . . ?
C21 C20 B1 125.21(14) . . ?
C25 C20 B1 117.65(14) . . ?
C3 C2 C1 121.66(15) . . ?
C3 C2 C7 126.75(14) . . ?
C1 C2 C7 111.58(13) . . ?
C6 C1 C2 119.06(15) . . ?
C6 C1 B1 134.19(15) . . ?
C2 C1 B1 106.71(13) . . ?
C24 C25 C20 121.78(16) . . ?
C24 C25 H25 119.1 . . ?
C20 C25 H25 119.1 . . ?
N1 C7 C2 103.13(12) . . ?
N1 C7 C26 112.57(13) . . ?
C2 C7 C26 113.28(13) . . ?
N1 C7 H7 109.2 . . ?
C2 C7 H7 109.2 . . ?
C26 C7 H7 109.3 . . ?
C13 C8 C9 120.90(14) . . ?
C13 C8 N1 120.29(13) . . ?
C9 C8 N1 118.78(13) . . ?
C5 C4 C3 120.91(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.5 . . ?
N1 B1 C20 125.87(14) . . ?
N1 B1 C1 105.54(14) . . ?
C20 B1 C1 128.41(14) . . ?
C17 C19 H19A 109.6 . . ?
C17 C19 H19B 109.4 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.4 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C20 121.41(16) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C24 C25 119.80(16) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C23 C22 C21 120.18(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C5 C6 C1 119.38(16) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C11 C12 C13 121.36(16) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C22 C23 C24 119.73(16) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.1 . . ?
C11 C10 C9 121.13(16) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C5 C6 120.64(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.8 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.4 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.6 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 999429'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 B Cl N2'
_chemical_formula_sum            'C15 H18 B Cl N2'
_chemical_formula_weight         272.57

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.9790(8)
_cell_length_b                   9.7780(3)
_cell_length_c                   17.0041(10)
_cell_angle_alpha                90
_cell_angle_beta                 127.218(6)
_cell_angle_gamma                90
_cell_volume                     1453.67(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    10902
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.250
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.146
0 -1 1 0.116
0 -1 -1 0.098
0 1 1 0.106
-1 0 0 0.129
1 0 0 0.131
0 0 1 0.130
0 0 -1 0.151
1 1 -1 0.142
-1 -1 1 0.100
-1 1 -1 0.156
1 -1 1 0.134
1 1 1 0.127
-1 1 1 0.115


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            10875
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3319
_reflns_number_gt                2623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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     
'w=1/[σ²(Fo²)+(0.0345P)²+0.9664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.106
_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_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
Cl1 Cl 0.54754(5) 0.22876(5) 0.13257(4) 0.03457(14) Uani 1 1 d . . . . .
N2 N 0.27827(17) 0.22512(15) 0.12058(11) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.30139(16) 0.04741(15) 0.03684(11) 0.0253(3) Uani 1 1 d . . . . .
B1 B 0.3353(2) 0.2014(2) 0.05411(15) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.2414(2) 0.28736(17) -0.04608(13) 0.0241(4) Uani 1 1 d . . . . .
C11 C 0.0888(2) 0.25277(18) -0.11910(13) 0.0265(4) Uani 1 1 d . . . . .
H11 H 0.0460 0.1805 -0.1079 0.032 Uiso 1 1 d R U . . .
C13 C 0.0602(3) 0.4313(2) -0.22525(15) 0.0378(5) Uani 1 1 d . . . . .
H13 H 0.0002 0.4793 -0.2844 0.045 Uiso 1 1 d R U . . .
C5 C 0.2261(2) 0.1111(2) 0.12888(14) 0.0320(4) Uani 1 1 d . . . . .
H5 H 0.1859 0.1029 0.1636 0.038 Uiso 1 1 d R U . . .
C4 C 0.3073(2) -0.05744(19) -0.01202(14) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.3454 -0.0529 -0.0481 0.037 Uiso 1 1 d R U . . .
C12 C -0.0008(2) 0.3232(2) -0.20768(14) 0.0340(4) Uani 1 1 d . . . . .
H12 H -0.1019 0.2974 -0.2552 0.041 Uiso 1 1 d R U . . .
C1 C 0.2370(2) 0.00049(19) 0.08002(15) 0.0304(4) Uani 1 1 d . . . . .
C3 C 0.2480(2) -0.1731(2) 0.00017(16) 0.0387(5) Uani 1 1 d . . . . .
H3 H 0.2396 -0.2593 -0.0258 0.046 Uiso 1 1 d R U . . .
C14 C 0.2102(3) 0.4675(2) -0.15490(16) 0.0399(5) Uani 1 1 d . . . . .
H14 H 0.2518 0.5405 -0.1664 0.048 Uiso 1 1 d R U . . .
C2 C 0.2020(3) -0.1370(2) 0.05800(17) 0.0405(5) Uani 1 1 d . . . . .
H2 H 0.1568 -0.1935 0.0778 0.049 Uiso 1 1 d R U . . .
C15 C 0.2998(2) 0.3959(2) -0.06675(15) 0.0341(4) Uani 1 1 d . . . . .
H15 H 0.4015 0.4210 -0.0202 0.041 Uiso 1 1 d R U . . .
C6 C 0.2739(2) 0.3548(2) 0.16616(14) 0.0336(4) Uani 1 1 d D . . . .
C7 C 0.3163(11) 0.4742(10) 0.1326(7) 0.0340(18) Uani 0.45 1 d D . P A 1
H7A H 0.4159 0.4596 0.1493 0.051 Uiso 0.45 1 calc R U P A 1
H7B H 0.3175 0.5557 0.1646 0.051 Uiso 0.45 1 calc R U P A 1
H7C H 0.2428 0.4842 0.0624 0.051 Uiso 0.45 1 calc R U P A 1
C8 C 0.1188(7) 0.3679(7) 0.1442(6) 0.0508(17) Uani 0.47 1 d D . P A 1
H8A H 0.0996 0.2886 0.1685 0.076 Uiso 0.47 1 calc R U P A 1
H8B H 0.0413 0.3753 0.0742 0.076 Uiso 0.47 1 calc R U P A 1
H8C H 0.1171 0.4482 0.1761 0.076 Uiso 0.47 1 calc R U P A 1
C9 C 0.3913(9) 0.3259(9) 0.2766(5) 0.056(2) Uani 0.5 1 d D . P A 1
H9A H 0.3574 0.2498 0.2946 0.084 Uiso 0.5 1 calc R U P A 1
H9B H 0.4018 0.4051 0.3136 0.084 Uiso 0.5 1 calc R U P A 1
H9C H 0.4882 0.3045 0.2910 0.084 Uiso 0.5 1 calc R U P A 1
C9A C 0.1076(7) 0.4041(8) 0.0980(5) 0.076(2) Uani 0.53 1 d D . P A 2
H9A1 H 0.0758 0.4114 0.0317 0.114 Uiso 0.53 1 calc R U P A 2
H9A2 H 0.0998 0.4919 0.1198 0.114 Uiso 0.53 1 calc R U P A 2
H9A3 H 0.0432 0.3398 0.0997 0.114 Uiso 0.53 1 calc R U P A 2
C7A C 0.3674(11) 0.4684(10) 0.1640(7) 0.064(3) Uani 0.55 1 d D . P A 2
H7A1 H 0.3339 0.4805 0.0976 0.097 Uiso 0.55 1 calc R U P A 2
H7A2 H 0.4737 0.4438 0.2059 0.097 Uiso 0.55 1 calc R U P A 2
H7A3 H 0.3534 0.5521 0.1871 0.097 Uiso 0.55 1 calc R U P A 2
C8A C 0.3274(10) 0.3428(10) 0.2706(5) 0.055(2) Uani 0.5 1 d D . P A 2
H8A1 H 0.4322 0.3135 0.3122 0.083 Uiso 0.5 1 calc R U P A 2
H8A2 H 0.2654 0.2771 0.2736 0.083 Uiso 0.5 1 calc R U P A 2
H8A3 H 0.3189 0.4300 0.2927 0.083 Uiso 0.5 1 calc R U P A 2


_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
Cl1 B1 1.876(2) . ?
N2 C5 1.299(2) . ?
N2 C6 1.502(2) . ?
N2 B1 1.606(2) . ?
N1 C4 1.346(2) . ?
N1 C1 1.370(2) . ?
N1 B1 1.536(2) . ?
B1 C10 1.596(3) . ?
C10 C15 1.390(3) . ?
C10 C11 1.395(2) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9299 . ?
C13 C14 1.373(3) . ?
C13 C12 1.377(3) . ?
C13 H13 0.9299 . ?
C5 C1 1.413(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.382(3) . ?
C4 H4 0.9299 . ?
C12 H12 0.9300 . ?
C1 C2 1.387(3) . ?
C3 C2 1.396(3) . ?
C3 H3 0.9300 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C6 C7 1.492(7) . ?
C6 C8 1.512(6) . ?
C6 C8A 1.500(6) . ?
C6 C9 1.530(6) . ?
C6 C9A 1.532(6) . ?
C6 C7A 1.528(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9A H9A1 0.9600 . ?
C9A H9A2 0.9600 . ?
C9A H9A3 0.9600 . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
C8A H8A1 0.9600 . ?
C8A H8A2 0.9600 . ?
C8A H8A3 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
C5 N2 C6 120.97(15) . . ?
C5 N2 B1 109.75(15) . . ?
C6 N2 B1 129.24(14) . . ?
C4 N1 C1 108.01(15) . . ?
C4 N1 B1 140.17(16) . . ?
C1 N1 B1 111.71(14) . . ?
N1 B1 C10 112.75(15) . . ?
N1 B1 N2 97.08(13) . . ?
C10 B1 N2 113.57(14) . . ?
N1 B1 Cl1 109.20(12) . . ?
C10 B1 Cl1 114.01(13) . . ?
N2 B1 Cl1 108.91(12) . . ?
C15 C10 C11 116.70(17) . . ?
C15 C10 B1 124.93(16) . . ?
C11 C10 B1 118.37(15) . . ?
C12 C11 C10 121.83(17) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.0 . . ?
C14 C13 C12 119.56(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N2 C5 C1 113.14(16) . . ?
N2 C5 H5 123.5 . . ?
C1 C5 H5 123.3 . . ?
N1 C4 C3 109.12(17) . . ?
N1 C4 H4 125.5 . . ?
C3 C4 H4 125.4 . . ?
C13 C12 C11 119.96(19) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 119.9 . . ?
N1 C1 C2 109.21(17) . . ?
N1 C1 C5 108.30(16) . . ?
C2 C1 C5 142.46(19) . . ?
C4 C3 C2 107.67(18) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.1 . . ?
C13 C14 C15 120.30(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.8 . . ?
C1 C2 C3 105.99(18) . . ?
C1 C2 H2 126.8 . . ?
C3 C2 H2 127.2 . . ?
C14 C15 C10 121.65(19) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.1 . . ?
C7 C6 N2 110.4(5) . . ?
C7 C6 C8 113.9(5) . . ?
N2 C6 C8 109.1(3) . . ?
N2 C6 C8A 115.6(4) . . ?
C7 C6 C9 112.8(5) . . ?
N2 C6 C9 102.2(3) . . ?
C8 C6 C9 107.7(4) . . ?
N2 C6 C9A 105.7(3) . . ?
C8A C6 C9A 110.8(4) . . ?
N2 C6 C7A 111.7(5) . . ?
C8A C6 C7A 107.3(5) . . ?
C9A C6 C7A 105.3(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C9A H9A1 109.5 . . ?
C6 C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C6 C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C6 C7A H7A1 109.5 . . ?
C6 C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6 C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C6 C8A H8A1 109.5 . . ?
C6 C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C6 C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 999430'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H29 B N2'
_chemical_formula_sum            'C24 H29 B N2'
_chemical_formula_weight         356.30

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.3910(9)
_cell_length_b                   11.9710(8)
_cell_length_c                   17.1839(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.239(7)
_cell_angle_gamma                90
_cell_volume                     2080.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    15276
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.065
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.051
1 0 0 0.023
0 -1 0 0.297
0 1 0 0.241
0 0 1 0.218
0 0 -1 0.165
0 -1 -1 0.306
0 -1 1 0.333


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15236
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         27.45
_reflns_number_total             4668
_reflns_number_gt                3387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0325P)²+1.2129P] 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         4668
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.25814(14) 0.25367(12) 0.26118(8) 0.0215(3) Uani 1 1 d . . .
N1 N 0.33631(15) 0.39571(12) 0.34805(9) 0.0251(3) Uani 1 1 d . . .
C11 C 0.25166(17) 0.04939(15) 0.24528(11) 0.0256(4) Uani 1 1 d . . .
C7 C 0.21356(17) 0.17090(16) 0.12743(11) 0.0262(4) Uani 1 1 d . . .
C15 C 0.27859(19) 0.02955(16) 0.33498(11) 0.0305(4) Uani 1 1 d . . .
H15 H 0.2892 0.1024 0.3617 0.037 Uiso 1 1 d R . .
C24 C 0.03756(19) 0.25071(16) 0.29647(12) 0.0329(4) Uani 1 1 d . . .
H24A H 0.0028 0.1949 0.2572 0.039 Uiso 1 1 d R . .
H24B H -0.0329 0.2983 0.3041 0.039 Uiso 1 1 d R . .
H24C H 0.0779 0.2151 0.3461 0.039 Uiso 1 1 d R . .
C6 C 0.24062(16) 0.15667(14) 0.21112(10) 0.0221(4) Uani 1 1 d . . .
B1 B 0.3748(2) 0.29547(17) 0.31062(11) 0.0229(4) Uani 1 1 d . . .
C12 C 0.21131(19) 0.28504(17) 0.08842(11) 0.0316(4) Uani 1 1 d . . .
H12 H 0.2361 0.3410 0.1308 0.038 Uiso 1 1 d R . .
C18 C 0.51401(17) 0.24035(14) 0.32946(10) 0.0246(4) Uani 1 1 d . . .
C1 C 0.20106(18) 0.41013(15) 0.32551(10) 0.0251(4) Uani 1 1 d . . .
C20 C 0.6879(2) 0.13187(17) 0.29238(13) 0.0352(5) Uani 1 1 d . . .
H20 H 0.7220 0.0968 0.2532 0.042 Uiso 1 1 d R . .
C8 C 0.1923(2) 0.07622(17) 0.07931(12) 0.0337(4) Uani 1 1 d . . .
H8 H 0.1708 0.0842 0.0240 0.040 Uiso 1 1 d R . .
C19 C 0.56671(18) 0.18569(16) 0.27181(11) 0.0289(4) Uani 1 1 d . . .
H19 H 0.5195 0.1854 0.2188 0.035 Uiso 1 1 d R . .
C2 C 0.1662(2) 0.50189(16) 0.36269(11) 0.0306(4) Uani 1 1 d . . .
H2 H 0.0811 0.5294 0.3584 0.037 Uiso 1 1 d R . .
C3 C 0.2863(2) 0.54719(16) 0.40938(12) 0.0352(5) Uani 1 1 d . . .
H3 H 0.2936 0.6108 0.4411 0.042 Uiso 1 1 d R . .
C23 C 0.58727(18) 0.23793(16) 0.40841(11) 0.0297(4) Uani 1 1 d . . .
H23 H 0.5548 0.2741 0.4478 0.036 Uiso 1 1 d R . .
C5 C 0.14006(17) 0.31997(15) 0.26800(10) 0.0251(4) Uani 1 1 d . . .
H5 H 0.1000 0.3535 0.2161 0.030 Uiso 1 1 d R . .
C17 C 0.1620(2) -0.03012(18) 0.35730(13) 0.0387(5) Uani 1 1 d . . .
H17A H 0.0820 0.0102 0.3355 0.046 Uiso 1 1 d R . .
H17B H 0.1758 -0.0334 0.4144 0.046 Uiso 1 1 d R . .
H17C H 0.1549 -0.1046 0.3360 0.046 Uiso 1 1 d R . .
C4 C 0.3885(2) 0.48118(16) 0.39953(11) 0.0318(4) Uani 1 1 d . . .
H4 H 0.4775 0.4919 0.4233 0.038 Uiso 1 1 d R . .
C9 C 0.2025(2) -0.02894(17) 0.11212(12) 0.0370(5) Uani 1 1 d . . .
H9 H 0.1879 -0.0914 0.0791 0.044 Uiso 1 1 d R . .
C10 C 0.23467(19) -0.04218(16) 0.19397(12) 0.0319(4) Uani 1 1 d . . .
H10 H 0.2451 -0.1138 0.2154 0.038 Uiso 1 1 d R . .
C16 C 0.4054(2) -0.03738(18) 0.36579(13) 0.0411(5) Uani 1 1 d . . .
H16A H 0.3955 -0.1107 0.3425 0.049 Uiso 1 1 d R . .
H16B H 0.4224 -0.0436 0.4229 0.049 Uiso 1 1 d R . .
H16C H 0.4780 0.0001 0.3511 0.049 Uiso 1 1 d R . .
C21 C 0.7578(2) 0.13041(17) 0.37101(13) 0.0377(5) Uani 1 1 d . . .
H21 H 0.8391 0.0943 0.3848 0.045 Uiso 1 1 d R . .
C22 C 0.7075(2) 0.18241(18) 0.42916(13) 0.0371(5) Uani 1 1 d . . .
H22 H 0.7541 0.1804 0.4823 0.045 Uiso 1 1 d R . .
C13 C 0.3115(2) 0.2905(2) 0.03550(12) 0.0431(5) Uani 1 1 d . . .
H13A H 0.2860 0.2391 -0.0082 0.052 Uiso 1 1 d R . .
H13B H 0.3975 0.2709 0.0666 0.052 Uiso 1 1 d R . .
H13C H 0.3137 0.3649 0.0150 0.052 Uiso 1 1 d R . .
C14 C 0.0730(2) 0.3137(2) 0.03922(13) 0.0438(5) Uani 1 1 d . . .
H14A H 0.0461 0.2588 -0.0021 0.053 Uiso 1 1 d R . .
H14B H 0.0740 0.3861 0.0155 0.053 Uiso 1 1 d R . .
H14C H 0.0118 0.3138 0.0735 0.053 Uiso 1 1 d 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
N2 B1 1.404(2) . ?
N2 C6 1.432(2) . ?
N2 C5 1.488(2) . ?
N1 C4 1.380(2) . ?
N1 C1 1.380(2) . ?
N1 B1 1.460(2) . ?
C11 C10 1.392(3) . ?
C11 C6 1.406(2) . ?
C11 C15 1.521(3) . ?
C7 C8 1.391(3) . ?
C7 C6 1.411(2) . ?
C7 C12 1.520(3) . ?
C15 C17 1.529(3) . ?
C15 C16 1.529(3) . ?
C15 H15 0.9801 . ?
C24 C5 1.517(3) . ?
C24 H24A 0.9601 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
B1 C18 1.555(3) . ?
C12 C14 1.530(3) . ?
C12 C13 1.532(3) . ?
C12 H12 0.9801 . ?
C18 C23 1.396(2) . ?
C18 C19 1.399(3) . ?
C1 C2 1.361(3) . ?
C1 C5 1.502(2) . ?
C20 C21 1.380(3) . ?
C20 C19 1.386(3) . ?
C20 H20 0.9299 . ?
C8 C9 1.374(3) . ?
C8 H8 0.9300 . ?
C19 H19 0.9300 . ?
C2 C3 1.427(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(3) . ?
C3 H3 0.9299 . ?
C23 C22 1.388(3) . ?
C23 H23 0.9300 . ?
C5 H5 0.9799 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9601 . ?
C17 H17C 0.9599 . ?
C4 H4 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9299 . ?
C10 H10 0.9299 . ?
C16 H16A 0.9602 . ?
C16 H16B 0.9599 . ?
C16 H16C 0.9601 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C13 H13A 0.9601 . ?
C13 H13B 0.9599 . ?
C13 H13C 0.9601 . ?
C14 H14A 0.9599 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9601 . ?

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
B1 N2 C6 128.76(15) . . ?
B1 N2 C5 112.07(14) . . ?
C6 N2 C5 119.08(13) . . ?
C4 N1 C1 108.23(15) . . ?
C4 N1 B1 141.69(17) . . ?
C1 N1 B1 110.07(14) . . ?
C10 C11 C6 117.93(17) . . ?
C10 C11 C15 119.08(16) . . ?
C6 C11 C15 122.98(16) . . ?
C8 C7 C6 118.37(17) . . ?
C8 C7 C12 119.09(16) . . ?
C6 C7 C12 122.51(16) . . ?
C11 C15 C17 110.78(16) . . ?
C11 C15 C16 112.12(17) . . ?
C17 C15 C16 109.74(16) . . ?
C11 C15 H15 108.1 . . ?
C17 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C5 C24 H24A 109.5 . . ?
C5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C6 C7 120.93(16) . . ?
C11 C6 N2 120.20(15) . . ?
C7 C6 N2 118.86(15) . . ?
N2 B1 N1 105.89(15) . . ?
N2 B1 C18 127.45(16) . . ?
N1 B1 C18 126.35(16) . . ?
C7 C12 C14 111.26(17) . . ?
C7 C12 C13 110.87(17) . . ?
C14 C12 C13 110.02(16) . . ?
C7 C12 H12 108.2 . . ?
C14 C12 H12 108.1 . . ?
C13 C12 H12 108.3 . . ?
C23 C18 C19 117.63(17) . . ?
C23 C18 B1 119.05(16) . . ?
C19 C18 B1 123.17(16) . . ?
C2 C1 N1 109.44(16) . . ?
C2 C1 C5 140.45(18) . . ?
N1 C1 C5 110.11(14) . . ?
C21 C20 C19 119.95(19) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.0 . . ?
C9 C8 C7 121.07(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C20 C19 C18 121.12(18) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.4 . . ?
C1 C2 C3 106.12(17) . . ?
C1 C2 H2 126.8 . . ?
C3 C2 H2 127.1 . . ?
C4 C3 C2 108.40(17) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.7 . . ?
C22 C23 C18 121.21(18) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
N2 C5 C1 101.75(14) . . ?
N2 C5 C24 112.73(15) . . ?
C1 C5 C24 113.72(15) . . ?
N2 C5 H5 109.4 . . ?
C1 C5 H5 109.4 . . ?
C24 C5 H5 109.5 . . ?
C15 C17 H17A 109.4 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C4 N1 107.80(17) . . ?
C3 C4 H4 126.1 . . ?
N1 C4 H4 126.1 . . ?
C8 C9 C10 120.15(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 121.44(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.2 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.3 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 C20 120.16(19) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.92(19) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.4 . . ?
C12 C14 H14B 109.7 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.3 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 999431'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H27 B N2'
_chemical_formula_sum            'C19 H27 B N2'
_chemical_formula_weight         294.24

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.3330(7)
_cell_length_b                   11.1231(10)
_cell_length_c                   12.0420(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.788(5)
_cell_angle_gamma                90
_cell_volume                     1709.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    23291
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.066
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.234
1 0 0 0.246
0 1 0 0.190
0 -1 0 0.128
0 0 1 0.101
0 0 -1 0.131


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23195
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         27.45
_reflns_number_total             3847
_reflns_number_gt                3229
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0453P)²+0.7445P] 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         3847
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C14 C 0.89973(9) 0.22042(11) 0.82995(10) 0.0210(2) Uani 1 1 d . . .
C5 C 0.65270(9) 0.21892(10) 0.94366(10) 0.0194(2) Uani 1 1 d . . .
H5 H 0.6431 0.1950 1.0182 0.023 Uiso 1 1 d R . .
N2 N 0.74419(7) 0.15410(9) 0.92356(9) 0.0191(2) Uani 1 1 d . . .
N1 N 0.76878(8) 0.35699(9) 0.90033(9) 0.0234(2) Uani 1 1 d . . .
C11 C 0.89447(10) 0.05560(12) 1.06221(12) 0.0278(3) Uani 1 1 d . . .
H11A H 0.9394 0.0849 1.0187 0.033 Uiso 1 1 d R . .
H11B H 0.9214 -0.0191 1.0987 0.033 Uiso 1 1 d R . .
H11C H 0.8917 0.1134 1.1205 0.033 Uiso 1 1 d R . .
C18 C 1.07128(10) 0.28036(11) 0.81577(11) 0.0256(3) Uani 1 1 d . . .
H18 H 1.1322 0.3253 0.8436 0.031 Uiso 1 1 d R . .
C6 C 0.54777(9) 0.20081(11) 0.84338(10) 0.0221(3) Uani 1 1 d . . .
C10 C 0.78419(9) 0.03601(10) 0.98056(10) 0.0206(2) Uani 1 1 d . . .
C19 C 0.99249(10) 0.28718(11) 0.87003(11) 0.0233(3) Uani 1 1 d . . .
H19 H 1.0014 0.3370 0.9342 0.028 Uiso 1 1 d R . .
C12 C 0.78913(12) -0.05838(12) 0.88997(12) 0.0328(3) Uani 1 1 d . . .
H12A H 0.7209 -0.0682 0.8359 0.039 Uiso 1 1 d R . .
H12B H 0.8122 -0.1336 0.9278 0.039 Uiso 1 1 d R . .
H12C H 0.8375 -0.0325 0.8493 0.039 Uiso 1 1 d R . .
C16 C 0.96791(10) 0.14018(11) 0.67855(11) 0.0262(3) Uani 1 1 d . . .
H16 H 0.9597 0.0906 0.6144 0.031 Uiso 1 1 d R . .
C1 C 0.68681(9) 0.34831(11) 0.94814(10) 0.0223(3) Uani 1 1 d . . .
C13 C 0.71837(11) -0.01297(13) 1.05515(13) 0.0321(3) Uani 1 1 d . . .
H13A H 0.7151 0.0456 1.1125 0.039 Uiso 1 1 d R . .
H13B H 0.7497 -0.0855 1.0929 0.039 Uiso 1 1 d R . .
H13C H 0.6489 -0.0300 1.0069 0.039 Uiso 1 1 d R . .
C2 C 0.79397(11) 0.47649(12) 0.89432(12) 0.0301(3) Uani 1 1 d . . .
H2 H 0.8462 0.5068 0.8650 0.036 Uiso 1 1 d R . .
C7 C 0.55970(11) 0.24369(13) 0.72722(11) 0.0288(3) Uani 1 1 d . . .
H7A H 0.4942 0.2347 0.6680 0.035 Uiso 1 1 d R . .
H7B H 0.6124 0.1965 0.7075 0.035 Uiso 1 1 d R . .
H7C H 0.5801 0.3268 0.7333 0.035 Uiso 1 1 d R . .
C15 C 0.88909(10) 0.14768(11) 0.73256(11) 0.0234(3) Uani 1 1 d . . .
H15 H 0.8280 0.1033 0.7032 0.028 Uiso 1 1 d R . .
B1 B 0.80727(10) 0.23708(12) 0.88466(11) 0.0206(3) Uani 1 1 d . . .
C17 C 1.05888(10) 0.20671(11) 0.72016(12) 0.0267(3) Uani 1 1 d . . .
H17 H 1.1116 0.2017 0.6840 0.032 Uiso 1 1 d R . .
C3 C 0.72858(11) 0.54235(12) 0.93921(13) 0.0344(3) Uani 1 1 d . . .
H3 H 0.7288 0.6256 0.9464 0.041 Uiso 1 1 d R . .
C4 C 0.65974(11) 0.46167(12) 0.97303(12) 0.0300(3) Uani 1 1 d . . .
H4 H 0.6069 0.4820 1.0058 0.036 Uiso 1 1 d R . .
C8 C 0.51411(10) 0.06921(12) 0.83051(12) 0.0306(3) Uani 1 1 d . . .
H8A H 0.4504 0.0615 0.7684 0.037 Uiso 1 1 d R . .
H8B H 0.5028 0.0416 0.9015 0.037 Uiso 1 1 d R . .
H8C H 0.5680 0.0217 0.8135 0.037 Uiso 1 1 d R . .
C9 C 0.46104(10) 0.27303(14) 0.87293(12) 0.0322(3) Uani 1 1 d . . .
H9A H 0.4760 0.3573 0.8715 0.039 Uiso 1 1 d R . .
H9B H 0.4578 0.2509 0.9489 0.039 Uiso 1 1 d R . .
H9C H 0.3950 0.2560 0.8171 0.039 Uiso 1 1 d 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
C14 C15 1.3978(18) . ?
C14 C19 1.4033(17) . ?
C14 B1 1.5675(17) . ?
C5 N2 1.4957(14) . ?
C5 C1 1.5056(17) . ?
C5 C6 1.5748(16) . ?
C5 H5 0.9799 . ?
N2 B1 1.4165(16) . ?
N2 C10 1.5065(15) . ?
N1 C1 1.3779(16) . ?
N1 C2 1.3780(16) . ?
N1 B1 1.4608(17) . ?
C11 C10 1.5301(17) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C18 C17 1.3835(19) . ?
C18 C19 1.3903(17) . ?
C18 H18 0.9300 . ?
C6 C8 1.5258(18) . ?
C6 C7 1.5290(17) . ?
C6 C9 1.5320(17) . ?
C10 C13 1.5261(17) . ?
C10 C12 1.5291(17) . ?
C19 H19 0.9300 . ?
C12 H12A 0.9601 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 C17 1.3852(19) . ?
C16 C15 1.3890(18) . ?
C16 H16 0.9300 . ?
C1 C4 1.3684(18) . ?
C13 H13A 0.9599 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C2 C3 1.364(2) . ?
C2 H2 0.9301 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9599 . ?
C7 H7C 0.9600 . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C3 C4 1.425(2) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8A 0.9601 . ?
C8 H8B 0.9599 . ?
C8 H8C 0.9599 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9601 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C14 C19 117.43(11) . . ?
C15 C14 B1 121.29(11) . . ?
C19 C14 B1 120.99(11) . . ?
N2 C5 C1 102.39(9) . . ?
N2 C5 C6 113.56(9) . . ?
C1 C5 C6 110.00(9) . . ?
N2 C5 H5 110.2 . . ?
C1 C5 H5 110.2 . . ?
C6 C5 H5 110.2 . . ?
B1 N2 C5 109.23(9) . . ?
B1 N2 C10 123.57(10) . . ?
C5 N2 C10 122.99(9) . . ?
C1 N1 C2 108.92(11) . . ?
C1 N1 B1 109.92(10) . . ?
C2 N1 B1 140.70(11) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.4 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C18 C19 119.90(12) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.1 . . ?
C8 C6 C7 108.15(11) . . ?
C8 C6 C9 107.88(11) . . ?
C7 C6 C9 109.50(11) . . ?
C8 C6 C5 111.76(10) . . ?
C7 C6 C5 110.95(10) . . ?
C9 C6 C5 108.53(10) . . ?
N2 C10 C13 113.04(10) . . ?
N2 C10 C12 110.86(10) . . ?
C13 C10 C12 108.99(11) . . ?
N2 C10 C11 108.46(9) . . ?
C13 C10 C11 106.37(10) . . ?
C12 C10 C11 108.95(11) . . ?
C18 C19 C14 121.33(12) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.4 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C17 C16 C15 120.03(12) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 120.1 . . ?
C4 C1 N1 108.55(11) . . ?
C4 C1 C5 142.43(12) . . ?
N1 C1 C5 108.66(10) . . ?
C10 C13 H13A 109.6 . . ?
C10 C13 H13B 109.4 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.4 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C2 N1 107.69(12) . . ?
C3 C2 H2 126.1 . . ?
N1 C2 H2 126.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.4 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C15 C14 121.36(12) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.4 . . ?
N2 B1 N1 106.73(10) . . ?
N2 B1 C14 132.54(11) . . ?
N1 B1 C14 120.70(11) . . ?
C18 C17 C16 119.94(12) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.0 . . ?
C2 C3 C4 108.25(12) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
C1 C4 C3 106.58(12) . . ?
C1 C4 H4 126.7 . . ?
C3 C4 H4 126.7 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.4 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.6 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 999432'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H27 B Cl N, C H2 Cl2'
_chemical_formula_sum            'C26 H29 B Cl3 N'
_chemical_formula_weight         472.66

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   10.3590(6)
_cell_length_b                   13.0260(12)
_cell_length_c                   18.498(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2496.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    16126
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.381
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.129
0 -1 -1 0.126
1 1 0 0.189
0 1 1 0.170
0 -1 1 0.065
-1 0 0 0.155
0 1 0 0.134
0 -1 0 0.087


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16082
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.35
_reflns_number_total             5485
_reflns_number_gt                4755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0143P)²+1.4856P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         5485
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.196
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.82111(6) 0.42472(4) 0.25739(3) 0.02363(12) Uani 1 1 d . . .
Cl2 Cl 0.66675(9) 0.65191(8) 0.45069(6) 0.0733(3) Uani 1 1 d . . .
Cl3 Cl 0.94258(9) 0.66646(8) 0.42510(5) 0.0630(3) Uani 1 1 d . . .
N1 N 0.86765(17) 0.21031(14) 0.28150(10) 0.0159(4) Uani 1 1 d . . .
C7 C 0.9767(2) 0.17050(18) 0.26295(12) 0.0182(4) Uani 1 1 d . . .
H7 H 0.9844 0.1061 0.2417 0.022 Uiso 1 1 d R . .
C8 C 0.7478(2) 0.15365(17) 0.27806(12) 0.0167(4) Uani 1 1 d . . .
C20 C 0.8222(2) 0.32962(17) 0.39680(12) 0.0207(5) Uani 1 1 d . . .
C6 C 1.1343(2) 0.39669(19) 0.33398(13) 0.0237(5) Uani 1 1 d . . .
H6 H 1.1086 0.4564 0.3574 0.028 Uiso 1 1 d R . .
C13 C 0.6655(2) 0.16688(17) 0.21859(12) 0.0198(5) Uani 1 1 d . . .
C9 C 0.7175(2) 0.08838(18) 0.33604(12) 0.0197(5) Uani 1 1 d . . .
C1 C 1.0432(2) 0.32483(18) 0.31353(12) 0.0193(5) Uani 1 1 d . . .
C3 C 1.2166(2) 0.2178(2) 0.26372(14) 0.0258(5) Uani 1 1 d . . .
H3 H 1.2426 0.1581 0.2403 0.031 Uiso 1 1 d R . .
C14 C 0.8118(2) 0.06507(19) 0.39693(12) 0.0236(5) Uani 1 1 d . . .
H14 H 0.8805 0.1167 0.3954 0.028 Uiso 1 1 d R . .
C21 C 0.6884(2) 0.34303(19) 0.40457(13) 0.0267(5) Uani 1 1 d . . .
H21 H 0.6363 0.3432 0.3636 0.032 Uiso 1 1 d R . .
C17 C 0.7015(2) 0.22750(18) 0.15142(12) 0.0216(5) Uani 1 1 d . . .
H17 H 0.7864 0.2587 0.1593 0.026 Uiso 1 1 d R . .
C2 C 1.0866(2) 0.23606(18) 0.27868(12) 0.0186(5) Uani 1 1 d . . .
C19 C 0.7114(3) 0.1546(2) 0.08657(13) 0.0311(6) Uani 1 1 d . . .
H19A H 0.7753 0.1030 0.0962 0.037 Uiso 1 1 d R . .
H19B H 0.7358 0.1929 0.0444 0.037 Uiso 1 1 d R . .
H19C H 0.6293 0.1224 0.0784 0.037 Uiso 1 1 d R . .
C10 C 0.5984(2) 0.03983(19) 0.33432(14) 0.0260(5) Uani 1 1 d . . .
H10 H 0.5756 -0.0036 0.3721 0.031 Uiso 1 1 d R . .
C25 C 0.8949(2) 0.3276(2) 0.46045(14) 0.0262(5) Uani 1 1 d . . .
H25 H 0.9837 0.3179 0.4574 0.031 Uiso 1 1 d R . .
C11 C 0.5126(2) 0.0540(2) 0.27785(15) 0.0283(6) Uani 1 1 d . . .
H11 H 0.4324 0.0220 0.2785 0.034 Uiso 1 1 d R . .
C16 C 0.8739(3) -0.0402(2) 0.38542(16) 0.0383(7) Uani 1 1 d . . .
H16A H 0.8081 -0.0921 0.3854 0.046 Uiso 1 1 d R . .
H16B H 0.9340 -0.0535 0.4238 0.046 Uiso 1 1 d R . .
H16C H 0.9185 -0.0410 0.3399 0.046 Uiso 1 1 d R . .
C22 C 0.6324(3) 0.3555(2) 0.47228(16) 0.0365(7) Uani 1 1 d . . .
H22 H 0.5437 0.3650 0.4763 0.044 Uiso 1 1 d R . .
B1 B 0.8896(3) 0.3222(2) 0.31930(14) 0.0182(5) Uani 1 1 d . . .
C4 C 1.3052(2) 0.2908(2) 0.28471(15) 0.0293(6) Uani 1 1 d . . .
H4 H 1.3925 0.2809 0.2755 0.035 Uiso 1 1 d R . .
C12 C 0.5468(2) 0.11599(19) 0.22055(14) 0.0239(5) Uani 1 1 d . . .
H12 H 0.4894 0.1242 0.1823 0.029 Uiso 1 1 d R . .
C5 C 1.2643(2) 0.3795(2) 0.31961(14) 0.0276(6) Uani 1 1 d . . .
H5 H 1.3249 0.4283 0.3335 0.033 Uiso 1 1 d R . .
C15 C 0.7474(3) 0.0712(2) 0.47122(14) 0.0326(6) Uani 1 1 d . . .
H15A H 0.7023 0.1353 0.4757 0.039 Uiso 1 1 d R . .
H15B H 0.8123 0.0666 0.5082 0.039 Uiso 1 1 d R . .
H15C H 0.6875 0.0155 0.4765 0.039 Uiso 1 1 d R . .
C18 C 0.6045(3) 0.3132(2) 0.13617(15) 0.0305(6) Uani 1 1 d . . .
H18A H 0.5220 0.2839 0.1246 0.037 Uiso 1 1 d R . .
H18B H 0.6343 0.3537 0.0961 0.037 Uiso 1 1 d R . .
H18C H 0.5963 0.3560 0.1782 0.037 Uiso 1 1 d R . .
C23 C 0.7075(3) 0.3540(2) 0.53350(16) 0.0408(7) Uani 1 1 d . . .
H23 H 0.6696 0.3634 0.5786 0.049 Uiso 1 1 d R . .
C24 C 0.8385(3) 0.3393(2) 0.52804(15) 0.0369(7) Uani 1 1 d . . .
H24 H 0.8891 0.3368 0.5695 0.044 Uiso 1 1 d R . .
C26 C 0.8086(3) 0.5849(2) 0.43137(17) 0.0450(7) Uani 1 1 d . . .
H26A H 0.8240 0.5348 0.4692 0.054 Uiso 1 1 d R . .
H26B H 0.7985 0.5481 0.3861 0.054 Uiso 1 1 d 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
Cl1 B1 1.897(3) . ?
Cl2 C26 1.746(3) . ?
Cl3 C26 1.751(3) . ?
N1 C7 1.289(3) . ?
N1 C8 1.445(3) . ?
N1 B1 1.633(3) . ?
C7 C2 1.453(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.402(3) . ?
C8 C9 1.404(3) . ?
C20 C25 1.398(3) . ?
C20 C21 1.404(3) . ?
C20 B1 1.598(3) . ?
C6 C1 1.382(3) . ?
C6 C5 1.390(3) . ?
C6 H6 0.9300 . ?
C13 C12 1.397(3) . ?
C13 C17 1.519(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.521(3) . ?
C1 C2 1.398(3) . ?
C1 B1 1.595(3) . ?
C3 C4 1.378(4) . ?
C3 C2 1.395(3) . ?
C3 H3 0.9300 . ?
C14 C16 1.529(4) . ?
C14 C15 1.529(3) . ?
C14 H14 0.9799 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9301 . ?
C17 C18 1.529(3) . ?
C17 C19 1.533(3) . ?
C17 H17 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9601 . ?
C19 H19C 0.9600 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C25 C24 1.388(4) . ?
C25 H25 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9599 . ?
C16 H16C 0.9601 . ?
C22 C23 1.374(4) . ?
C22 H22 0.9301 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C5 H5 0.9301 . ?
C15 H15A 0.9601 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9601 . ?
C18 H18C 0.9600 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9299 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
C7 N1 C8 122.36(19) . . ?
C7 N1 B1 110.54(18) . . ?
C8 N1 B1 126.47(17) . . ?
N1 C7 C2 113.4(2) . . ?
N1 C7 H7 123.4 . . ?
C2 C7 H7 123.2 . . ?
C13 C8 C9 122.5(2) . . ?
C13 C8 N1 119.61(19) . . ?
C9 C8 N1 117.86(19) . . ?
C25 C20 C21 116.6(2) . . ?
C25 C20 B1 121.3(2) . . ?
C21 C20 B1 122.1(2) . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 120.1 . . ?
C12 C13 C8 117.2(2) . . ?
C12 C13 C17 119.0(2) . . ?
C8 C13 C17 123.8(2) . . ?
C10 C9 C8 117.2(2) . . ?
C10 C9 C14 119.8(2) . . ?
C8 C9 C14 122.9(2) . . ?
C6 C1 C2 117.8(2) . . ?
C6 C1 B1 132.6(2) . . ?
C2 C1 B1 109.5(2) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C9 C14 C16 110.2(2) . . ?
C9 C14 C15 112.0(2) . . ?
C16 C14 C15 110.8(2) . . ?
C9 C14 H14 108.0 . . ?
C16 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.3 . . ?
C13 C17 C18 111.7(2) . . ?
C13 C17 C19 109.54(19) . . ?
C18 C17 C19 110.6(2) . . ?
C13 C17 H17 108.3 . . ?
C18 C17 H17 108.3 . . ?
C19 C17 H17 108.3 . . ?
C3 C2 C1 122.9(2) . . ?
C3 C2 C7 128.1(2) . . ?
C1 C2 C7 109.0(2) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.4 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C24 C25 C20 122.0(2) . . ?
C24 C25 H25 119.0 . . ?
C20 C25 H25 119.0 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.3 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.4 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 120.0 . . ?
C1 B1 C20 119.7(2) . . ?
C1 B1 N1 97.45(18) . . ?
C20 B1 N1 112.16(18) . . ?
C1 B1 Cl1 108.53(16) . . ?
C20 B1 Cl1 109.60(17) . . ?
N1 B1 Cl1 108.52(15) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 119.8 . . ?
C11 C12 C13 121.6(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.4 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.2 . . ?
Cl2 C26 Cl3 112.18(17) . . ?
Cl2 C26 H26A 109.1 . . ?
Cl3 C26 H26A 109.0 . . ?
Cl2 C26 H26B 109.4 . . ?
Cl3 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.35
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 999433'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 B Cl2 N, C H2 Cl2'
_chemical_formula_sum            'C20 H24 B Cl4 N'
_chemical_formula_weight         431.01

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   12.3332(4)
_cell_length_b                   13.0120(2)
_cell_length_c                   14.1703(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.492(3)
_cell_angle_gamma                90
_cell_volume                     2156.63(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    18862
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.553
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.180
0 1 0 0.222
1 0 0 0.098
-1 0 0 0.035
1 0 -1 0.119
-1 0 1 0.108
0 0 -1 0.113
0 0 1 0.141


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_diffrn_ambient_temperature      150(1)
_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 Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            18640
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4874
_reflns_number_gt                3863
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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     
'w=1/[σ²(Fo²)+(0.0675P)²+10.7607P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4874
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.1998
_refine_ls_wR_factor_gt          0.1820
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.91062(8) 0.22973(7) 0.83277(7) 0.0252(2) Uani 1 1 d . . . . .
Cl2 Cl 0.91107(8) 0.23182(7) 0.62076(7) 0.0255(2) Uani 1 1 d . . . . .
Cl3 Cl 0.56779(15) 0.29486(12) 0.54966(13) 0.0650(5) Uani 1 1 d . . . . .
Cl4 Cl 0.49161(15) 0.20388(15) 0.70599(15) 0.0717(5) Uani 1 1 d . . . . .
N1 N 0.9224(3) 0.0456(2) 0.7282(2) 0.0150(6) Uani 1 1 d . . . . .
C8 C 0.8070(3) 0.0051(3) 0.6944(3) 0.0161(7) Uani 1 1 d . . . . .
C3 C 1.2263(3) -0.0072(3) 0.8161(3) 0.0226(8) Uani 1 1 d . . . . .
H3 H 1.2358 -0.0781 0.8188 0.027 Uiso 1 1 d R U . . .
C12 C 0.6463(3) -0.0555(3) 0.5629(3) 0.0218(8) Uani 1 1 d . . . . .
H12 H 0.6104 -0.0698 0.4959 0.026 Uiso 1 1 d R U . . .
C17 C 0.8183(3) -0.0011(3) 0.5163(3) 0.0218(8) Uani 1 1 d . . . . .
H17 H 0.8911 0.0334 0.5489 0.026 Uiso 1 1 d R U . . .
C2 C 1.1182(3) 0.0368(3) 0.7845(2) 0.0164(7) Uani 1 1 d . . . . .
C1 C 1.0992(3) 0.1439(3) 0.7789(3) 0.0179(7) Uani 1 1 d . . . . .
C10 C 0.6417(3) -0.0553(3) 0.7307(3) 0.0236(8) Uani 1 1 d . . . . .
H10 H 0.6026 -0.0699 0.7755 0.028 Uiso 1 1 d R U . . .
C6 C 1.1937(3) 0.2076(3) 0.8068(3) 0.0228(8) Uani 1 1 d . . . . .
H6 H 1.1848 0.2786 0.8047 0.027 Uiso 1 1 d R U . . .
C7 C 1.0098(3) -0.0157(3) 0.7533(3) 0.0169(7) Uani 1 1 d . . . . .
H7 H 1.0032 -0.0870 0.7513 0.020 Uiso 1 1 d R U . . .
C9 C 0.7522(3) -0.0152(3) 0.7654(3) 0.0194(7) Uani 1 1 d . . . . .
C14 C 0.8090(4) -0.0032(3) 0.8771(3) 0.0237(8) Uani 1 1 d . . . . .
H14 H 0.8829 0.0306 0.8879 0.028 Uiso 1 1 d R U . . .
C13 C 0.7568(3) -0.0150(3) 0.5930(3) 0.0178(7) Uani 1 1 d . . . . .
C19 C 0.8440(4) -0.1059(3) 0.4786(3) 0.0300(9) Uani 1 1 d . . . . .
H19A H 0.8924 -0.1450 0.5332 0.036 Uiso 1 1 d R U . . .
H19B H 0.8821 -0.0956 0.4298 0.036 Uiso 1 1 d R U . . .
H19C H 0.7738 -0.1424 0.4490 0.036 Uiso 1 1 d R U . . .
C5 C 1.3029(3) 0.1644(3) 0.8389(3) 0.0270(8) Uani 1 1 d . . . . .
H5 H 1.3663 0.2075 0.8572 0.032 Uiso 1 1 d R U . . .
C11 C 0.5889(3) -0.0741(3) 0.6304(3) 0.0248(8) Uani 1 1 d . . . . .
H11 H 0.5145 -0.0994 0.6082 0.030 Uiso 1 1 d R U . . .
B1 B 0.9654(4) 0.1639(3) 0.7412(3) 0.0175(8) Uani 1 1 d . . . . .
C16 C 0.8317(4) -0.1092(4) 0.9276(3) 0.0353(10) Uani 1 1 d . . . . .
H16A H 0.7605 -0.1446 0.9169 0.042 Uiso 1 1 d R U . . .
H16B H 0.8691 -0.1008 0.9977 0.042 Uiso 1 1 d R U . . .
H16C H 0.8797 -0.1484 0.8993 0.042 Uiso 1 1 d R U . . .
C15 C 0.7383(4) 0.0643(4) 0.9237(3) 0.0363(11) Uani 1 1 d . . . . .
H15A H 0.7197 0.1275 0.8872 0.044 Uiso 1 1 d R U . . .
H15B H 0.7814 0.0788 0.9917 0.044 Uiso 1 1 d R U . . .
H15C H 0.6691 0.0290 0.9213 0.044 Uiso 1 1 d R U . . .
C18 C 0.7493(4) 0.0663(3) 0.4290(3) 0.0296(9) Uani 1 1 d . . . . .
H18A H 0.6829 0.0293 0.3899 0.036 Uiso 1 1 d R U . . .
H18B H 0.7958 0.0835 0.3883 0.036 Uiso 1 1 d R U . . .
H18C H 0.7261 0.1282 0.4541 0.036 Uiso 1 1 d R U . . .
C4 C 1.3195(4) 0.0586(3) 0.8435(3) 0.0288(9) Uani 1 1 d . . . . .
H4 H 1.3933 0.0321 0.8656 0.035 Uiso 1 1 d R U . . .
C20 C 0.6017(4) 0.2124(4) 0.6512(4) 0.0427(12) Uani 1 1 d . . . . .
H20A H 0.6705 0.2370 0.7010 0.051 Uiso 1 1 d R U . . .
H20B H 0.6175 0.1445 0.6307 0.051 Uiso 1 1 d R U . . .


_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
Cl1 B1 1.852(4) . ?
Cl2 B1 1.849(4) . ?
Cl3 C20 1.737(5) . ?
Cl4 C20 1.767(6) . ?
N1 C7 1.297(5) . ?
N1 C8 1.449(4) . ?
N1 B1 1.619(5) . ?
C8 C13 1.397(5) . ?
C8 C9 1.404(5) . ?
C3 C4 1.386(6) . ?
C3 C2 1.388(5) . ?
C3 H3 0.9300 . ?
C12 C11 1.379(6) . ?
C12 C13 1.397(5) . ?
C12 H12 0.9300 . ?
C17 C13 1.521(5) . ?
C17 C18 1.535(6) . ?
C17 C19 1.534(6) . ?
C17 H17 0.9799 . ?
C2 C1 1.412(5) . ?
C2 C7 1.440(5) . ?
C1 C6 1.382(5) . ?
C1 B1 1.586(5) . ?
C10 C11 1.384(6) . ?
C10 C9 1.396(5) . ?
C10 H10 0.9299 . ?
C6 C5 1.396(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C14 1.522(5) . ?
C14 C15 1.528(6) . ?
C14 C16 1.537(6) . ?
C14 H14 0.9801 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9599 . ?
C5 C4 1.391(6) . ?
C5 H5 0.9300 . ?
C11 H11 0.9301 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9601 . ?
C15 H15B 0.9598 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9601 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9601 . ?
C4 H4 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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
C7 N1 C8 120.7(3) . . ?
C7 N1 B1 109.9(3) . . ?
C8 N1 B1 129.4(3) . . ?
C13 C8 C9 123.0(3) . . ?
C13 C8 N1 118.5(3) . . ?
C9 C8 N1 118.5(3) . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.2 . . ?
C11 C12 C13 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C13 C17 C18 111.7(3) . . ?
C13 C17 C19 110.4(3) . . ?
C18 C17 C19 110.5(3) . . ?
C13 C17 H17 107.9 . . ?
C18 C17 H17 108.0 . . ?
C19 C17 H17 108.2 . . ?
C3 C2 C1 123.4(3) . . ?
C3 C2 C7 127.4(3) . . ?
C1 C2 C7 109.2(3) . . ?
C6 C1 C2 117.8(3) . . ?
C6 C1 B1 133.7(3) . . ?
C2 C1 B1 108.5(3) . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.6 . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.2 . . ?
N1 C7 C2 113.7(3) . . ?
N1 C7 H7 123.2 . . ?
C2 C7 H7 123.0 . . ?
C10 C9 C8 117.1(3) . . ?
C10 C9 C14 118.8(3) . . ?
C8 C9 C14 124.0(3) . . ?
C9 C14 C15 111.8(4) . . ?
C9 C14 C16 110.4(3) . . ?
C15 C14 C16 111.1(3) . . ?
C9 C14 H14 107.8 . . ?
C15 C14 H14 107.7 . . ?
C16 C14 H14 107.9 . . ?
C8 C13 C12 117.1(3) . . ?
C8 C13 C17 123.7(3) . . ?
C12 C13 C17 119.1(3) . . ?
C17 C19 H19A 109.6 . . ?
C17 C19 H19B 109.3 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.6 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.2 . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 120.1 . . ?
C1 B1 N1 98.6(3) . . ?
C1 B1 Cl2 115.0(3) . . ?
N1 B1 Cl2 109.9(2) . . ?
C1 B1 Cl1 114.3(3) . . ?
N1 B1 Cl1 109.9(2) . . ?
Cl2 B1 Cl1 108.7(2) . . ?
C14 C16 H16A 109.6 . . ?
C14 C16 H16B 109.7 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.2 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.4 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.6 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 119.7 . . ?
Cl3 C20 Cl4 112.7(3) . . ?
Cl3 C20 H20A 108.8 . . ?
Cl4 C20 H20A 108.6 . . ?
Cl3 C20 H20B 109.4 . . ?
Cl4 C20 H20B 109.3 . . ?
H20A C20 H20B 107.8 . . ?

_refine_diff_density_max         1.235
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.109

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 999434'
