# 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_H2LBr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H27 Br N2 O'
_chemical_formula_sum            'C26 H27 Br N2 O'
_chemical_formula_weight         463.41

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/N

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

_cell_length_a                   9.7624(4)
_cell_length_b                   13.2901(4)
_cell_length_c                   18.1845(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.391(3)
_cell_angle_gamma                90.00
_cell_volume                     2285.29(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2840
_cell_measurement_theta_min      3.0867
_cell_measurement_theta_max      27.4228

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.3722
_exptl_crystal_size_mid          0.2736
_exptl_crystal_size_min          0.1094
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    1.818
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'Ω SCANS'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11387
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5235
_reflns_number_gt                3595
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  MERCURY

_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 > 2σ(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)+(0.0435P)²+0.4898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5235
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0437(3) 0.23140(19) 0.60613(13) 0.0253(6) Uani 1 1 d . . .
H1 H 1.0990 0.1760 0.6258 0.030 Uiso 1 1 calc R . .
C2 C 0.8672(3) 0.32665(19) 0.54161(13) 0.0240(5) Uani 1 1 d . . .
C3 C 0.9690(3) 0.38840(19) 0.58248(13) 0.0236(5) Uani 1 1 d . . .
C4 C 0.7259(3) 0.3481(2) 0.49029(14) 0.0330(6) Uani 1 1 d . . .
H4A H 0.7035 0.4180 0.4940 0.050 Uiso 1 1 calc R . .
H4B H 0.6557 0.3076 0.5049 0.050 Uiso 1 1 calc R . .
H4C H 0.7274 0.3327 0.4389 0.050 Uiso 1 1 calc R . .
C5 C 0.9758(3) 0.5002(2) 0.58854(14) 0.0302(6) Uani 1 1 d . . .
H5A H 0.8909 0.5287 0.5572 0.045 Uiso 1 1 calc R . .
H5B H 1.0559 0.5243 0.5720 0.045 Uiso 1 1 calc R . .
H5C H 0.9851 0.5197 0.6404 0.045 Uiso 1 1 calc R . .
C6 C 0.8440(3) 0.13610(18) 0.52836(13) 0.0249(6) Uani 1 1 d . . .
C7 C 0.8502(3) 0.1019(2) 0.45689(14) 0.0279(6) Uani 1 1 d . . .
C8 C 0.7771(3) 0.0136(2) 0.43127(14) 0.0338(7) Uani 1 1 d . . .
H8 H 0.7781 -0.0108 0.3835 0.041 Uiso 1 1 calc R . .
C9 C 0.7033(3) -0.0389(2) 0.47427(16) 0.0368(7) Uani 1 1 d . . .
C10 C 0.7030(3) -0.0027(2) 0.54580(16) 0.0397(7) Uani 1 1 d . . .
H10 H 0.6550 -0.0387 0.5755 0.048 Uiso 1 1 calc R . .
C11 C 0.7719(3) 0.0854(2) 0.57444(15) 0.0329(6) Uani 1 1 d . . .
C12 C 0.9328(3) 0.1563(3) 0.40964(16) 0.0458(8) Uani 1 1 d . . .
H12A H 0.8827 0.2160 0.3886 0.069 Uiso 1 1 calc R . .
H12B H 0.9445 0.1133 0.3693 0.069 Uiso 1 1 calc R . .
H12C H 1.0240 0.1745 0.4409 0.069 Uiso 1 1 calc R . .
C13 C 0.6284(4) -0.1363(2) 0.4455(2) 0.0578(10) Uani 1 1 d . . .
H13A H 0.6121 -0.1394 0.3913 0.087 Uiso 1 1 calc R . .
H13B H 0.5395 -0.1390 0.4591 0.087 Uiso 1 1 calc R . .
H13C H 0.6860 -0.1922 0.4680 0.087 Uiso 1 1 calc R . .
C14 C 0.7707(4) 0.1254(2) 0.65186(17) 0.0530(9) Uani 1 1 d . . .
H14A H 0.8630 0.1179 0.6855 0.079 Uiso 1 1 calc R . .
H14B H 0.7030 0.0885 0.6715 0.079 Uiso 1 1 calc R . .
H14C H 0.7452 0.1953 0.6479 0.079 Uiso 1 1 calc R . .
C15 C 1.2124(2) 0.35765(19) 0.67267(13) 0.0253(6) Uani 1 1 d . . .
H15A H 1.2479 0.3038 0.7083 0.030 Uiso 1 1 calc R . .
H15B H 1.1976 0.4162 0.7016 0.030 Uiso 1 1 calc R . .
C16 C 1.3209(3) 0.38218(18) 0.62923(14) 0.0260(6) Uani 1 1 d . . .
C17 C 1.4720(3) 0.3837(2) 0.67264(14) 0.0263(6) Uani 1 1 d . . .
C18 C 1.5652(3) 0.4523(2) 0.64995(16) 0.0369(7) Uani 1 1 d . . .
H18 H 1.5305 0.4968 0.6102 0.044 Uiso 1 1 calc R . .
C19 C 1.7050(3) 0.4531(3) 0.68605(16) 0.0416(7) Uani 1 1 d . . .
H19 H 1.7642 0.4998 0.6716 0.050 Uiso 1 1 calc R . .
C20 C 1.7620(3) 0.3850(2) 0.74469(15) 0.0352(7) Uani 1 1 d . . .
C21 C 1.9095(3) 0.3813(3) 0.78128(18) 0.0461(8) Uani 1 1 d . . .
H21 H 1.9711 0.4267 0.7675 0.055 Uiso 1 1 calc R . .
C22 C 1.9601(3) 0.3121(3) 0.83580(19) 0.0547(9) Uani 1 1 d . . .
H22 H 2.0567 0.3095 0.8582 0.066 Uiso 1 1 calc R . .
C23 C 1.8698(3) 0.2447(3) 0.85888(18) 0.0531(9) Uani 1 1 d . . .
H23 H 1.9066 0.1978 0.8966 0.064 Uiso 1 1 calc R . .
C24 C 1.7265(3) 0.2467(2) 0.82637(16) 0.0419(7) Uani 1 1 d . . .
H24 H 1.6668 0.2022 0.8429 0.050 Uiso 1 1 calc R . .
C25 C 1.6703(3) 0.3160(2) 0.76812(14) 0.0292(6) Uani 1 1 d . . .
C26 C 1.5237(3) 0.3184(2) 0.73064(14) 0.0266(6) Uani 1 1 d . . .
H26 H 1.4621 0.2745 0.7461 0.032 Uiso 1 1 calc R . .
N1 N 0.9172(2) 0.22804(16) 0.55679(11) 0.0247(5) Uani 1 1 d . . .
N2 N 1.0773(2) 0.32708(16) 0.62244(11) 0.0234(5) Uani 1 1 d . . .
O1 O 1.28598(19) 0.40237(15) 0.56191(10) 0.0366(5) Uani 1 1 d . . .
Br1 Br 1.24582(4) 0.11649(2) 0.767354(15) 0.04604(13) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N2 1.328(3) . ?
C1 N1 1.334(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(3) . ?
C2 N1 1.402(3) . ?
C2 C4 1.488(3) . ?
C3 N2 1.389(3) . ?
C3 C5 1.490(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.392(3) . ?
C6 C11 1.394(4) . ?
C6 N1 1.445(3) . ?
C7 C8 1.393(4) . ?
C7 C12 1.502(4) . ?
C8 C9 1.377(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(4) . ?
C9 C13 1.514(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9300 . ?
C11 C14 1.508(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N2 1.463(3) . ?
C15 C16 1.506(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.216(3) . ?
C16 C17 1.490(3) . ?
C17 C26 1.362(4) . ?
C17 C18 1.420(4) . ?
C18 C19 1.359(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.404(4) . ?
C19 H19 0.9300 . ?
C20 C25 1.418(4) . ?
C20 C21 1.429(4) . ?
C21 C22 1.352(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.393(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.409(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.424(3) . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 108.6(2) . . ?
N2 C1 H1 125.7 . . ?
N1 C1 H1 125.7 . . ?
C3 C2 N1 106.6(2) . . ?
C3 C2 C4 131.7(2) . . ?
N1 C2 C4 121.7(2) . . ?
C2 C3 N2 106.9(2) . . ?
C2 C3 C5 131.0(2) . . ?
N2 C3 C5 122.2(2) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 123.3(2) . . ?
C7 C6 N1 118.5(2) . . ?
C11 C6 N1 118.2(2) . . ?
C6 C7 C8 116.7(2) . . ?
C6 C7 C12 122.1(2) . . ?
C8 C7 C12 121.2(2) . . ?
C9 C8 C7 122.3(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 C13 120.9(3) . . ?
C10 C9 C13 120.4(3) . . ?
C9 C10 C11 122.1(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C6 116.9(2) . . ?
C10 C11 C14 122.2(3) . . ?
C6 C11 C14 120.9(2) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 112.02(19) . . ?
N2 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O1 C16 C17 121.5(2) . . ?
O1 C16 C15 121.2(2) . . ?
C17 C16 C15 117.2(2) . . ?
C26 C17 C18 119.5(2) . . ?
C26 C17 C16 121.9(2) . . ?
C18 C17 C16 118.5(2) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 121.5(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C25 118.9(2) . . ?
C19 C20 C21 122.6(3) . . ?
C25 C20 C21 118.4(3) . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 119.4(2) . . ?
C24 C25 C26 122.1(3) . . ?
C20 C25 C26 118.4(2) . . ?
C17 C26 C25 121.3(3) . . ?
C17 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C1 N1 C2 108.7(2) . . ?
C1 N1 C6 124.2(2) . . ?
C2 N1 C6 127.1(2) . . ?
C1 N2 C3 109.3(2) . . ?
C1 N2 C15 122.7(2) . . ?
C3 N2 C15 127.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.9(3) . . . . ?
C4 C2 C3 N2 178.0(3) . . . . ?
N1 C2 C3 C5 179.4(3) . . . . ?
C4 C2 C3 C5 -1.8(5) . . . . ?
C11 C6 C7 C8 1.4(4) . . . . ?
N1 C6 C7 C8 -179.4(2) . . . . ?
C11 C6 C7 C12 -177.9(3) . . . . ?
N1 C6 C7 C12 1.3(4) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C12 C7 C8 C9 178.5(3) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C7 C8 C9 C13 -178.3(3) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C13 C9 C10 C11 179.2(3) . . . . ?
C9 C10 C11 C6 -0.8(4) . . . . ?
C9 C10 C11 C14 179.5(3) . . . . ?
C7 C6 C11 C10 -0.6(4) . . . . ?
N1 C6 C11 C10 -179.8(2) . . . . ?
C7 C6 C11 C14 179.1(3) . . . . ?
N1 C6 C11 C14 -0.1(4) . . . . ?
N2 C15 C16 O1 20.0(3) . . . . ?
N2 C15 C16 C17 -161.8(2) . . . . ?
O1 C16 C17 C26 -146.1(3) . . . . ?
C15 C16 C17 C26 35.7(3) . . . . ?
O1 C16 C17 C18 30.8(4) . . . . ?
C15 C16 C17 C18 -147.4(2) . . . . ?
C26 C17 C18 C19 -0.3(4) . . . . ?
C16 C17 C18 C19 -177.2(3) . . . . ?
C17 C18 C19 C20 1.9(5) . . . . ?
C18 C19 C20 C25 -2.0(4) . . . . ?
C18 C19 C20 C21 177.2(3) . . . . ?
C19 C20 C21 C22 -177.8(3) . . . . ?
C25 C20 C21 C22 1.4(4) . . . . ?
C20 C21 C22 C23 -1.6(5) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C25 1.3(5) . . . . ?
C23 C24 C25 C20 -1.4(4) . . . . ?
C23 C24 C25 C26 177.5(3) . . . . ?
C19 C20 C25 C24 179.4(3) . . . . ?
C21 C20 C25 C24 0.2(4) . . . . ?
C19 C20 C25 C26 0.4(4) . . . . ?
C21 C20 C25 C26 -178.8(2) . . . . ?
C18 C17 C26 C25 -1.3(4) . . . . ?
C16 C17 C26 C25 175.5(2) . . . . ?
C24 C25 C26 C17 -177.7(2) . . . . ?
C20 C25 C26 C17 1.2(4) . . . . ?
N2 C1 N1 C2 -0.7(3) . . . . ?
N2 C1 N1 C6 -177.6(2) . . . . ?
C3 C2 N1 C1 1.0(3) . . . . ?
C4 C2 N1 C1 -178.0(2) . . . . ?
C3 C2 N1 C6 177.8(2) . . . . ?
C4 C2 N1 C6 -1.3(4) . . . . ?
C7 C6 N1 C1 -99.7(3) . . . . ?
C11 C6 N1 C1 79.6(3) . . . . ?
C7 C6 N1 C2 84.0(3) . . . . ?
C11 C6 N1 C2 -96.7(3) . . . . ?
N1 C1 N2 C3 0.1(3) . . . . ?
N1 C1 N2 C15 -177.5(2) . . . . ?
C2 C3 N2 C1 0.5(3) . . . . ?
C5 C3 N2 C1 -179.7(2) . . . . ?
C2 C3 N2 C15 177.9(2) . . . . ?
C5 C3 N2 C15 -2.3(4) . . . . ?
C16 C15 N2 C1 94.0(3) . . . . ?
C16 C15 N2 C3 -83.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 1003569'
#######################################################################
#
#                 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_HLtBu


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H39 B N2 O'
_chemical_formula_sum            'C19 H39 B N2 O'
_chemical_formula_weight         322.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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


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

_cell_length_a                   10.0790(7)
_cell_length_b                   13.6684(7)
_cell_length_c                   15.3802(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.472(5)
_cell_angle_gamma                90.00
_cell_volume                     2116.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3937
_cell_measurement_theta_min      3.0331
_cell_measurement_theta_max      27.4232

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5098
_exptl_crystal_size_mid          0.3364
_exptl_crystal_size_min          0.2418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.011
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18885
_diffrn_reflns_av_R_equivalents  0.1228
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4851
_reflns_number_gt                2774
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    sir-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ortep
_computing_publication_material  mecury

_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 > 2σ(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)+(0.1807P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4851
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1412
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.3115
_refine_ls_wR_factor_gt          0.2345
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C -0.0969(2) 0.60128(16) 0.17926(15) 0.0353(5) Uani 1 1 d . . .
H1 H -0.0849 0.6499 0.1362 0.042 Uiso 1 1 calc R . .
C2 C -0.1893(3) 0.5004(2) 0.2690(2) 0.0541(8) Uani 1 1 d . . .
H2 H -0.2544 0.4660 0.2997 0.065 Uiso 1 1 calc R . .
C3 C -0.0571(3) 0.48846(19) 0.27827(19) 0.0493(7) Uani 1 1 d . . .
H3 H -0.0115 0.4443 0.3168 0.059 Uiso 1 1 calc R . .
C4 C -0.3470(2) 0.6130(2) 0.18052(19) 0.0502(7) Uani 1 1 d . . .
C5 C -0.3342(4) 0.6759(4) 0.1017(3) 0.0992(16) Uani 1 1 d . . .
H5A H -0.2799 0.7333 0.1169 0.149 Uiso 1 1 calc R . .
H5B H -0.4226 0.6971 0.0803 0.149 Uiso 1 1 calc R . .
H5C H -0.2919 0.6384 0.0562 0.149 Uiso 1 1 calc R . .
C6 C -0.4408(4) 0.5297(3) 0.1636(4) 0.1114(18) Uani 1 1 d . . .
H6A H -0.5277 0.5552 0.1435 0.167 Uiso 1 1 calc R . .
H6B H -0.4503 0.4924 0.2174 0.167 Uiso 1 1 calc R . .
H6C H -0.4059 0.4869 0.1188 0.167 Uiso 1 1 calc R . .
C7 C -0.3929(4) 0.6726(4) 0.2580(3) 0.1096(17) Uani 1 1 d . . .
H7A H -0.3315 0.7272 0.2693 0.164 Uiso 1 1 calc R . .
H7B H -0.3941 0.6305 0.3096 0.164 Uiso 1 1 calc R . .
H7C H -0.4823 0.6981 0.2447 0.164 Uiso 1 1 calc R . .
C8 C 0.1422(2) 0.57027(16) 0.21349(17) 0.0379(6) Uani 1 1 d . . .
H8A H 0.1688 0.5474 0.1557 0.045 Uiso 1 1 calc R . .
H8B H 0.1924 0.5315 0.2582 0.045 Uiso 1 1 calc R . .
C9 C 0.1800(2) 0.67922(15) 0.22421(15) 0.0324(5) Uani 1 1 d . . .
H9 H 0.2759 0.6853 0.2110 0.039 Uiso 1 1 calc R . .
C10 C 0.1640(2) 0.72138(17) 0.31771(16) 0.0412(6) Uani 1 1 d . . .
C11 C 0.2375(3) 0.8194(2) 0.3220(2) 0.0568(8) Uani 1 1 d . . .
H11A H 0.2317 0.8473 0.3804 0.085 Uiso 1 1 calc R . .
H11B H 0.1968 0.8644 0.2790 0.085 Uiso 1 1 calc R . .
H11C H 0.3309 0.8091 0.3094 0.085 Uiso 1 1 calc R . .
C12 C 0.2247(4) 0.6531(2) 0.3866(2) 0.0646(9) Uani 1 1 d . . .
H12A H 0.2221 0.6843 0.4439 0.097 Uiso 1 1 calc R . .
H12B H 0.3170 0.6390 0.3735 0.097 Uiso 1 1 calc R . .
H12C H 0.1740 0.5919 0.3870 0.097 Uiso 1 1 calc R . .
C13 C 0.0185(3) 0.7424(2) 0.33594(19) 0.0520(7) Uani 1 1 d . . .
H13A H -0.0300 0.6805 0.3396 0.078 Uiso 1 1 calc R . .
H13B H -0.0213 0.7822 0.2887 0.078 Uiso 1 1 calc R . .
H13C H 0.0138 0.7778 0.3911 0.078 Uiso 1 1 calc R . .
C14 C 0.2179(3) 0.67856(18) 0.01738(18) 0.0474(7) Uani 1 1 d . . .
H14A H 0.2694 0.7067 -0.0300 0.057 Uiso 1 1 calc R . .
H14B H 0.2804 0.6391 0.0544 0.057 Uiso 1 1 calc R . .
C15 C 0.1148(3) 0.6092(2) -0.0238(2) 0.0686(9) Uani 1 1 d . . .
H15A H 0.0617 0.5807 0.0217 0.103 Uiso 1 1 calc R . .
H15B H 0.1597 0.5568 -0.0546 0.103 Uiso 1 1 calc R . .
H15C H 0.0565 0.6454 -0.0651 0.103 Uiso 1 1 calc R . .
C16 C 0.0382(3) 0.8242(2) 0.02942(18) 0.0471(6) Uani 1 1 d . . .
H16A H 0.0661 0.8530 -0.0259 0.057 Uiso 1 1 calc R . .
H16B H -0.0307 0.7745 0.0149 0.057 Uiso 1 1 calc R . .
C17 C -0.0234(3) 0.9043(2) 0.0832(2) 0.0636(9) Uani 1 1 d . . .
H17A H -0.0462 0.8778 0.1398 0.095 Uiso 1 1 calc R . .
H17B H -0.1039 0.9289 0.0525 0.095 Uiso 1 1 calc R . .
H17C H 0.0403 0.9580 0.0919 0.095 Uiso 1 1 calc R . .
C18 C 0.2885(2) 0.84512(18) 0.09790(17) 0.0428(6) Uani 1 1 d . . .
H18A H 0.2579 0.8967 0.1376 0.051 Uiso 1 1 calc R . .
H18B H 0.3608 0.8087 0.1292 0.051 Uiso 1 1 calc R . .
C19 C 0.3456(4) 0.8946(2) 0.0182(2) 0.0654(9) Uani 1 1 d . . .
H19A H 0.3871 0.8451 -0.0179 0.098 Uiso 1 1 calc R . .
H19B H 0.4122 0.9431 0.0374 0.098 Uiso 1 1 calc R . .
H19C H 0.2739 0.9271 -0.0158 0.098 Uiso 1 1 calc R . .
B1 B 0.1654(3) 0.76971(18) 0.07668(17) 0.0347(6) Uani 1 1 d . . .
N1 N -0.21304(19) 0.57132(14) 0.20712(14) 0.0398(5) Uani 1 1 d . . .
N2 N -0.00023(19) 0.55231(12) 0.22141(13) 0.0360(5) Uani 1 1 d . . .
O1 O 0.10849(13) 0.73425(10) 0.16280(10) 0.0313(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N2 1.328(3) . ?
C1 N1 1.329(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.344(4) . ?
C2 N1 1.372(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C6 1.496(5) . ?
C4 C5 1.496(5) . ?
C4 N1 1.506(3) . ?
C4 C7 1.531(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N2 1.467(3) . ?
C8 C9 1.544(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.385(3) . ?
C9 C10 1.564(3) . ?
C9 H9 1.0000 . ?
C10 C12 1.521(4) . ?
C10 C13 1.532(4) . ?
C10 C11 1.530(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.525(4) . ?
C14 B1 1.645(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.521(4) . ?
C16 B1 1.626(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.533(4) . ?
C18 B1 1.636(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
B1 O1 1.544(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 109.0(2) . . ?
N2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C3 C2 N1 107.6(2) . . ?
C3 C2 H2 126.2 . . ?
N1 C2 H2 126.2 . . ?
C2 C3 N2 107.1(2) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
C6 C4 C5 111.8(4) . . ?
C6 C4 N1 108.2(3) . . ?
C5 C4 N1 109.3(2) . . ?
C6 C4 C7 109.3(3) . . ?
C5 C4 C7 111.4(4) . . ?
N1 C4 C7 106.7(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 112.97(18) . . ?
N2 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 C8 109.40(17) . . ?
O1 C9 C10 110.83(18) . . ?
C8 C9 C10 114.76(19) . . ?
O1 C9 H9 107.2 . . ?
C8 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
C12 C10 C13 110.3(2) . . ?
C12 C10 C11 109.1(2) . . ?
C13 C10 C11 107.1(2) . . ?
C12 C10 C9 111.1(2) . . ?
C13 C10 C9 112.0(2) . . ?
C11 C10 C9 107.1(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 B1 118.1(2) . . ?
C15 C14 H14A 107.8 . . ?
B1 C14 H14A 107.8 . . ?
C15 C14 H14B 107.8 . . ?
B1 C14 H14B 107.8 . . ?
H14A C14 H14B 107.1 . . ?
C14 C15 H15A 109.5 . . ?
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 . . ?
C17 C16 B1 114.8(2) . . ?
C17 C16 H16A 108.6 . . ?
B1 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
B1 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 B1 115.2(2) . . ?
C19 C18 H18A 108.5 . . ?
B1 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
B1 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 B1 C16 102.27(18) . . ?
O1 B1 C18 109.47(19) . . ?
C16 B1 C18 112.2(2) . . ?
O1 B1 C14 112.23(19) . . ?
C16 B1 C14 111.4(2) . . ?
C18 B1 C14 109.15(19) . . ?
C1 N1 C2 108.1(2) . . ?
C1 N1 C4 126.0(2) . . ?
C2 N1 C4 125.7(2) . . ?
C1 N2 C3 108.23(19) . . ?
C1 N2 C8 125.11(19) . . ?
C3 N2 C8 126.5(2) . . ?
C9 O1 B1 123.64(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.2(3) . . . . ?
N2 C8 C9 O1 -57.7(3) . . . . ?
N2 C8 C9 C10 67.6(3) . . . . ?
O1 C9 C10 C12 171.5(2) . . . . ?
C8 C9 C10 C12 46.9(3) . . . . ?
O1 C9 C10 C13 47.6(2) . . . . ?
C8 C9 C10 C13 -76.9(2) . . . . ?
O1 C9 C10 C11 -69.5(2) . . . . ?
C8 C9 C10 C11 166.0(2) . . . . ?
C17 C16 B1 O1 55.3(3) . . . . ?
C17 C16 B1 C18 -61.9(3) . . . . ?
C17 C16 B1 C14 175.4(2) . . . . ?
C19 C18 B1 O1 -173.9(2) . . . . ?
C19 C18 B1 C16 -61.1(3) . . . . ?
C19 C18 B1 C14 62.9(3) . . . . ?
C15 C14 B1 O1 69.3(3) . . . . ?
C15 C14 B1 C16 -44.7(3) . . . . ?
C15 C14 B1 C18 -169.2(2) . . . . ?
N2 C1 N1 C2 -0.3(3) . . . . ?
N2 C1 N1 C4 175.5(2) . . . . ?
C3 C2 N1 C1 0.3(3) . . . . ?
C3 C2 N1 C4 -175.5(3) . . . . ?
C6 C4 N1 C1 136.2(3) . . . . ?
C5 C4 N1 C1 14.2(4) . . . . ?
C7 C4 N1 C1 -106.4(4) . . . . ?
C6 C4 N1 C2 -48.7(4) . . . . ?
C5 C4 N1 C2 -170.7(3) . . . . ?
C7 C4 N1 C2 68.7(4) . . . . ?
N1 C1 N2 C3 0.1(3) . . . . ?
N1 C1 N2 C8 -175.0(2) . . . . ?
C2 C3 N2 C1 0.1(3) . . . . ?
C2 C3 N2 C8 175.1(2) . . . . ?
C9 C8 N2 C1 49.8(3) . . . . ?
C9 C8 N2 C3 -124.4(3) . . . . ?
C8 C9 O1 B1 -99.2(2) . . . . ?
C10 C9 O1 B1 133.23(19) . . . . ?
C16 B1 O1 C9 177.09(18) . . . . ?
C18 B1 O1 C9 -63.8(2) . . . . ?
C14 B1 O1 C9 57.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 1003570'
#######################################################################
#
#                 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_HLBEt3Mes

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42.50 H55 B N2 O'
_chemical_formula_weight         620.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   11.7096(6)
_cell_length_b                   15.6144(9)
_cell_length_c                   22.0422(18)
_cell_angle_alpha                85.313(6)
_cell_angle_beta                 86.194(6)
_cell_angle_gamma                68.487(5)
_cell_volume                     3734.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5634
_cell_measurement_theta_min      2.8640
_cell_measurement_theta_max      24.7661

_exptl_crystal_description       'colourless block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_F_000             1348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3095
_exptl_crystal_size_mid          0.1773
_exptl_crystal_size_min          0.0840
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            13011
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.867
_diffrn_reflns_theta_max         24.802
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measured_fraction_theta_full 0.782
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_Laue_measured_fraction_full 0.782
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_point_group_measured_fraction_full 0.782
_reflns_number_total             13011
_reflns_number_gt                7373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    MERCURY
_computing_publication_material  POV-RAY

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+2.1234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13011
_refine_ls_number_parameters     888
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.056
_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
C32 C 0.9554(6) 0.3793(4) 0.0526(3) 0.065(2) Uani 1 1 d . . . . .
H32A H 0.9530 0.3197 0.0689 0.098 Uiso 1 1 calc R U . . .
H32B H 0.8822 0.4124 0.0291 0.098 Uiso 1 1 calc R U . . .
H32C H 0.9575 0.4159 0.0862 0.098 Uiso 1 1 calc R U . . .
C62 C 0.3554(6) 0.8512(4) 0.4579(3) 0.058(2) Uani 1 1 d . . . . .
H62A H 0.2943 0.8268 0.4764 0.088 Uiso 1 1 calc R U . . .
H62B H 0.3144 0.9067 0.4319 0.088 Uiso 1 1 calc R U . . .
H62C H 0.3969 0.8669 0.4901 0.088 Uiso 1 1 calc R U . . .
C64 C 0.3349(6) 0.6216(4) 0.4521(3) 0.059(2) Uani 1 1 d . . . . .
H64A H 0.2807 0.6812 0.4344 0.088 Uiso 1 1 calc R U . . .
H64B H 0.2857 0.5917 0.4768 0.088 Uiso 1 1 calc R U . . .
H64C H 0.3798 0.5822 0.4194 0.088 Uiso 1 1 calc R U . . .
C79A C 0.8171(13) -0.0396(8) 0.7282(6) 0.074(5) Uani 0.485(14) 1 d DG U P A 2
C80A C 0.8069(13) 0.0360(10) 0.6879(5) 0.071(5) Uani 0.485(14) 1 d DG U P A 2
H80A H 0.8158 0.0290 0.6453 0.085 Uiso 0.485(14) 1 calc R U P A 2
C81A C 0.7835(13) 0.1218(8) 0.7101(7) 0.082(5) Uani 0.485(14) 1 d G U P A 2
H81A H 0.7765 0.1735 0.6826 0.099 Uiso 0.485(14) 1 calc R U P A 2
C82A C 0.7704(16) 0.1321(9) 0.7725(7) 0.116(7) Uani 0.485(14) 1 d G U P A 2
H82A H 0.7544 0.1908 0.7877 0.139 Uiso 0.485(14) 1 calc R U P A 2
C83A C 0.7806(17) 0.0566(12) 0.8128(5) 0.121(7) Uani 0.485(14) 1 d G U P A 2
H83A H 0.7717 0.0636 0.8554 0.146 Uiso 0.485(14) 1 calc R U P A 2
C84A C 0.8040(15) -0.0293(10) 0.7906(5) 0.100(7) Uani 0.485(14) 1 d DG U P A 2
H84A H 0.8110 -0.0809 0.8181 0.120 Uiso 0.485(14) 1 calc R U P A 2
C85A C 0.844(3) -0.1280(10) 0.7046(10) 0.117(9) Uani 0.485(14) 1 d D U P A 2
H85A H 0.7691 -0.1301 0.6880 0.176 Uiso 0.485(14) 1 calc R U P A 2
H85B H 0.8718 -0.1763 0.7373 0.176 Uiso 0.485(14) 1 calc R U P A 2
H85C H 0.9078 -0.1380 0.6722 0.176 Uiso 0.485(14) 1 calc R U P A 2
C79B C 0.7974(14) 0.0676(10) 0.7629(7) 0.123(7) Uani 0.515(14) 1 d DG U P A 1
C80B C 0.8540(14) -0.0092(13) 0.8017(5) 0.113(7) Uani 0.515(14) 1 d DG U P A 1
H80B H 0.8743 -0.0014 0.8414 0.136 Uiso 0.515(14) 1 calc R U P A 1
C81B C 0.8809(15) -0.0973(11) 0.7824(8) 0.134(8) Uani 0.515(14) 1 d G U P A 1
H81B H 0.9197 -0.1497 0.8090 0.161 Uiso 0.515(14) 1 calc R U P A 1
C82B C 0.8512(17) -0.1087(11) 0.7244(9) 0.142(8) Uani 0.515(14) 1 d G U P A 1
H82B H 0.8696 -0.1689 0.7112 0.170 Uiso 0.515(14) 1 calc R U P A 1
C83B C 0.7946(16) -0.0319(15) 0.6856(6) 0.137(8) Uani 0.515(14) 1 d G U P A 1
H83B H 0.7743 -0.0397 0.6459 0.165 Uiso 0.515(14) 1 calc R U P A 1
C84B C 0.7677(14) 0.0562(13) 0.7048(6) 0.118(8) Uani 0.515(14) 1 d DG U P A 1
H84B H 0.7289 0.1086 0.6783 0.141 Uiso 0.515(14) 1 calc R U P A 1
C85B C 0.761(3) 0.1585(13) 0.7810(11) 0.165(11) Uani 0.515(14) 1 d D U P A 1
H85D H 0.6810 0.1750 0.8031 0.248 Uiso 0.515(14) 1 calc R U P A 1
H85E H 0.7540 0.2009 0.7450 0.248 Uiso 0.515(14) 1 calc R U P A 1
H85F H 0.8220 0.1628 0.8076 0.248 Uiso 0.515(14) 1 calc R U P A 1
C66 C 0.2482(8) 0.6018(5) 0.2285(5) 0.082(3) Uani 1 1 d . . . . .
H66 H 0.3161 0.6035 0.2030 0.099 Uiso 1 1 calc R U . . .
C67 C 0.2481(8) 0.6116(5) 0.2891(4) 0.072(2) Uani 1 1 d . . . . .
H67 H 0.3163 0.6193 0.3059 0.086 Uiso 1 1 calc R U . . .
C65 C 0.1523(8) 0.5897(4) 0.2039(3) 0.060(2) Uani 1 1 d . . . . .
H65 H 0.1546 0.5818 0.1615 0.072 Uiso 1 1 calc R U . . .
C72 C 0.2880(8) 0.5858(3) 0.6979(2) 0.097(3) Uani 1 1 d G U . B 4
H72 H 0.2657 0.5794 0.6583 0.116 Uiso 1 1 calc R U . B 4
C73 C 0.4102(7) 0.5682(3) 0.7092(3) 0.107(3) Uani 1 1 d G U . B 4
H73 H 0.4714 0.5498 0.6774 0.128 Uiso 1 1 calc R U . B 4
C74 C 0.4429(5) 0.5774(4) 0.7671(4) 0.115(3) Uani 1 1 d G U . B 4
H74 H 0.5264 0.5654 0.7749 0.138 Uiso 1 1 calc R U . B 4
C75 C 0.3534(8) 0.6043(4) 0.8137(3) 0.116(4) Uani 1 1 d G U . B 4
H75 H 0.3757 0.6106 0.8533 0.140 Uiso 1 1 calc R U . B 4
C76 C 0.2312(7) 0.6219(3) 0.8024(3) 0.097(3) Uani 1 1 d G U . B 4
H76 H 0.1701 0.6402 0.8342 0.116 Uiso 1 1 calc R U . B 4
C77 C 0.1986(5) 0.6126(3) 0.7445(4) 0.088(3) Uani 1 1 d G U . B 4
C78 C 0.0722(12) 0.6340(8) 0.7278(6) 0.144(7) Uani 0.807(18) 1 d . U P B 4
H78A H 0.0169 0.6533 0.7636 0.216 Uiso 0.807(18) 1 calc R U P B 4
H78B H 0.0644 0.5791 0.7128 0.216 Uiso 0.807(18) 1 calc R U P B 4
H78C H 0.0503 0.6839 0.6958 0.216 Uiso 0.807(18) 1 calc R U P B 4
C1 C 1.2762(5) 0.2294(4) -0.1143(3) 0.0352(16) Uani 1 1 d . . . . .
H1 H 1.2276 0.2275 -0.0783 0.042 Uiso 1 1 calc R U . . .
C2 C 1.3840(5) 0.1919(4) -0.2004(3) 0.0353(16) Uani 1 1 d . . . . .
C3 C 1.3825(5) 0.2757(4) -0.1870(3) 0.0356(16) Uani 1 1 d . . . . .
C4 C 1.4415(6) 0.1343(4) -0.2525(3) 0.059(2) Uani 1 1 d . . . . .
H4A H 1.4761 0.1688 -0.2826 0.088 Uiso 1 1 calc R U . . .
H4B H 1.3793 0.1181 -0.2715 0.088 Uiso 1 1 calc R U . . .
H4C H 1.5070 0.0778 -0.2379 0.088 Uiso 1 1 calc R U . . .
C5 C 1.4394(6) 0.3382(4) -0.2205(3) 0.057(2) Uani 1 1 d . . . . .
H5A H 1.3747 0.3965 -0.2331 0.085 Uiso 1 1 calc R U . . .
H5B H 1.4859 0.3087 -0.2566 0.085 Uiso 1 1 calc R U . . .
H5C H 1.4947 0.3502 -0.1938 0.085 Uiso 1 1 calc R U . . .
C6 C 1.2925(6) 0.0791(4) -0.1479(3) 0.0379(17) Uani 1 1 d . . . . .
C7 C 1.3751(7) 0.0041(4) -0.1156(3) 0.0480(19) Uani 1 1 d . . . . .
C8 C 1.3476(8) -0.0751(5) -0.1082(3) 0.066(2) Uani 1 1 d . . . . .
H8 H 1.4032 -0.1283 -0.0876 0.079 Uiso 1 1 calc R U . . .
C9 C 1.2435(10) -0.0794(5) -0.1297(4) 0.071(3) Uani 1 1 d . . . . .
C10 C 1.1655(7) -0.0033(5) -0.1619(3) 0.061(2) Uani 1 1 d . . . . .
H10 H 1.0938 -0.0066 -0.1777 0.073 Uiso 1 1 calc R U . . .
C11 C 1.1885(7) 0.0785(4) -0.1720(3) 0.0440(18) Uani 1 1 d . . . . .
C12 C 1.4893(7) 0.0075(5) -0.0913(3) 0.076(2) Uani 1 1 d . . . . .
H12A H 1.5426 0.0172 -0.1253 0.115 Uiso 1 1 calc R U . . .
H12B H 1.5327 -0.0508 -0.0685 0.115 Uiso 1 1 calc R U . . .
H12C H 1.4677 0.0584 -0.0643 0.115 Uiso 1 1 calc R U . . .
C13 C 1.2121(10) -0.1666(5) -0.1169(4) 0.120(4) Uani 1 1 d . . . . .
H13A H 1.2804 -0.2200 -0.1316 0.179 Uiso 1 1 calc R U . . .
H13B H 1.1376 -0.1592 -0.1379 0.179 Uiso 1 1 calc R U . . .
H13C H 1.1982 -0.1762 -0.0729 0.179 Uiso 1 1 calc R U . . .
C14 C 1.1023(6) 0.1597(5) -0.2060(3) 0.064(2) Uani 1 1 d . . . . .
H14A H 1.0684 0.2110 -0.1793 0.097 Uiso 1 1 calc R U . . .
H14B H 1.0354 0.1440 -0.2203 0.097 Uiso 1 1 calc R U . . .
H14C H 1.1462 0.1779 -0.2411 0.097 Uiso 1 1 calc R U . . .
C15 C 1.2857(5) 0.3814(4) -0.1000(3) 0.0375(17) Uani 1 1 d . . . . .
H15A H 1.1955 0.4123 -0.0952 0.045 Uiso 1 1 calc R U . . .
H15B H 1.3183 0.4244 -0.1240 0.045 Uiso 1 1 calc R U . . .
C16 C 1.3418(6) 0.3593(4) -0.0363(3) 0.0344(17) Uani 1 1 d . . . . .
H16 H 1.3100 0.4170 -0.0137 0.041 Uiso 1 1 calc R U . . .
C17 C 1.4799(6) 0.3293(4) -0.0429(3) 0.0326(16) Uani 1 1 d . . . . .
C18 C 1.5519(6) 0.2377(4) -0.0385(3) 0.0392(17) Uani 1 1 d . . . . .
H18 H 1.5139 0.1933 -0.0311 0.047 Uiso 1 1 calc R U . . .
C19 C 1.6817(6) 0.2073(5) -0.0446(3) 0.0433(18) Uani 1 1 d . . . . .
C20 C 1.7560(7) 0.1133(5) -0.0407(3) 0.054(2) Uani 1 1 d . . . . .
H20 H 1.7192 0.0680 -0.0346 0.064 Uiso 1 1 calc R U . . .
C21 C 1.8815(7) 0.0865(6) -0.0457(3) 0.066(2) Uani 1 1 d . . . . .
H21 H 1.9309 0.0228 -0.0417 0.079 Uiso 1 1 calc R U . . .
C22 C 1.9368(7) 0.1504(7) -0.0562(4) 0.074(2) Uani 1 1 d . . . . .
H22 H 2.0237 0.1304 -0.0611 0.089 Uiso 1 1 calc R U . . .
C23 C 1.8674(7) 0.2431(6) -0.0598(3) 0.064(2) Uani 1 1 d . . . . .
H23 H 1.9068 0.2868 -0.0657 0.077 Uiso 1 1 calc R U . . .
C24 C 1.7373(7) 0.2741(5) -0.0546(3) 0.0469(19) Uani 1 1 d . . . . .
C25 C 1.6619(7) 0.3686(5) -0.0588(3) 0.051(2) Uani 1 1 d . . . . .
H25 H 1.6982 0.4141 -0.0650 0.061 Uiso 1 1 calc R U . . .
C26 C 1.5383(7) 0.3944(4) -0.0540(3) 0.0443(18) Uani 1 1 d . . . . .
H26 H 1.4891 0.4581 -0.0582 0.053 Uiso 1 1 calc R U . . .
C27 C 1.2151(6) 0.3958(4) 0.0893(3) 0.055(2) Uani 1 1 d . . . . .
H27A H 1.1932 0.4564 0.0662 0.067 Uiso 1 1 calc R U . . .
H27B H 1.1552 0.4028 0.1242 0.067 Uiso 1 1 calc R U . . .
C28 C 1.3415(7) 0.3708(5) 0.1138(3) 0.066(2) Uani 1 1 d . . . . .
H28A H 1.3630 0.3123 0.1384 0.100 Uiso 1 1 calc R U . . .
H28B H 1.3419 0.4195 0.1392 0.100 Uiso 1 1 calc R U . . .
H28C H 1.4018 0.3645 0.0798 0.100 Uiso 1 1 calc R U . . .
C29 C 1.2151(6) 0.2238(4) 0.0838(3) 0.051(2) Uani 1 1 d . . . . .
H29A H 1.2968 0.1991 0.1020 0.062 Uiso 1 1 calc R U . . .
H29B H 1.1525 0.2374 0.1177 0.062 Uiso 1 1 calc R U . . .
C30 C 1.2013(6) 0.1489(4) 0.0477(3) 0.058(2) Uani 1 1 d . . . . .
H30A H 1.1169 0.1689 0.0341 0.088 Uiso 1 1 calc R U . . .
H30B H 1.2198 0.0918 0.0736 0.088 Uiso 1 1 calc R U . . .
H30C H 1.2585 0.1379 0.0121 0.088 Uiso 1 1 calc R U . . .
C31 C 1.0701(5) 0.3635(4) 0.0112(3) 0.0452(19) Uani 1 1 d . . . . .
H31A H 1.0641 0.4232 -0.0101 0.054 Uiso 1 1 calc R U . . .
H31B H 1.0703 0.3216 -0.0202 0.054 Uiso 1 1 calc R U . . .
C33 C 0.4811(5) 0.7652(4) 0.6164(3) 0.0317(16) Uani 1 1 d . . . . .
H33 H 0.4341 0.7670 0.5825 0.038 Uiso 1 1 calc R U . . .
C34 C 0.6257(5) 0.7198(4) 0.6834(3) 0.0311(15) Uani 1 1 d . . . . .
C35 C 0.5427(6) 0.8026(4) 0.6986(3) 0.0329(16) Uani 1 1 d . U . . .
C36 C 0.7403(6) 0.6574(4) 0.7130(3) 0.0503(19) Uani 1 1 d . . . . .
H36A H 0.7459 0.6805 0.7523 0.075 Uiso 1 1 calc R U . . .
H36B H 0.8118 0.6558 0.6867 0.075 Uiso 1 1 calc R U . . .
H36C H 0.7384 0.5951 0.7194 0.075 Uiso 1 1 calc R U . . .
C37 C 0.5388(6) 0.8613(4) 0.7500(3) 0.054(2) Uani 1 1 d . . . . .
H37A H 0.4562 0.8828 0.7694 0.081 Uiso 1 1 calc R U . . .
H37B H 0.5593 0.9146 0.7341 0.081 Uiso 1 1 calc R U . . .
H37C H 0.5984 0.8249 0.7802 0.081 Uiso 1 1 calc R U . . .
C38 C 0.3518(6) 0.9166(4) 0.6499(3) 0.0319(16) Uani 1 1 d . . . . .
C39 C 0.3720(6) 0.9909(4) 0.6199(3) 0.0436(18) Uani 1 1 d . . . . .
C40 C 0.2709(7) 1.0729(4) 0.6122(3) 0.053(2) Uani 1 1 d . . . . .
H40 H 0.2822 1.1254 0.5918 0.063 Uiso 1 1 calc R U . . .
C41 C 0.1563(7) 1.0790(5) 0.6334(3) 0.054(2) Uani 1 1 d . . . . .
C42 C 0.1405(6) 1.0030(5) 0.6655(3) 0.056(2) Uani 1 1 d . . . . .
H42 H 0.0613 1.0080 0.6818 0.067 Uiso 1 1 calc R U . . .
C43 C 0.2387(6) 0.9200(4) 0.6740(3) 0.0387(17) Uani 1 1 d . . . . .
C44 C 0.4961(6) 0.9847(4) 0.5942(3) 0.063(2) Uani 1 1 d . . . . .
H44A H 0.5268 0.9349 0.5661 0.095 Uiso 1 1 calc R U . . .
H44B H 0.5528 0.9718 0.6274 0.095 Uiso 1 1 calc R U . . .
H44C H 0.4900 1.0433 0.5722 0.095 Uiso 1 1 calc R U . . .
C45 C 0.0468(7) 1.1676(4) 0.6233(3) 0.090(3) Uani 1 1 d . . . . .
H45A H 0.0704 1.2204 0.6290 0.135 Uiso 1 1 calc R U . . .
H45B H -0.0200 1.1678 0.6525 0.135 Uiso 1 1 calc R U . . .
H45C H 0.0192 1.1720 0.5817 0.135 Uiso 1 1 calc R U . . .
C46 C 0.2201(6) 0.8383(4) 0.7078(3) 0.055(2) Uani 1 1 d . . . . .
H46A H 0.2282 0.7914 0.6792 0.083 Uiso 1 1 calc R U . . .
H46B H 0.1379 0.8578 0.7276 0.083 Uiso 1 1 calc R U . . .
H46C H 0.2820 0.8123 0.7388 0.083 Uiso 1 1 calc R U . . .
C47 C 0.6421(5) 0.6147(3) 0.5966(3) 0.0357(17) Uani 1 1 d . . . . .
H47A H 0.5819 0.5850 0.5921 0.043 Uiso 1 1 calc R U . . .
H47B H 0.7119 0.5700 0.6191 0.043 Uiso 1 1 calc R U . . .
C48 C 0.6885(6) 0.6391(4) 0.5335(3) 0.0331(16) Uani 1 1 d . . . . .
H48 H 0.7182 0.5825 0.5098 0.040 Uiso 1 1 calc R U . . .
C49 C 0.7962(6) 0.6703(4) 0.5399(3) 0.0320(16) Uani 1 1 d . . . . .
C50 C 0.7783(6) 0.7618(4) 0.5346(3) 0.0343(16) Uani 1 1 d . . . . .
H50 H 0.6990 0.8057 0.5262 0.041 Uiso 1 1 calc R U . . .
C51 C 0.8757(7) 0.7920(4) 0.5415(3) 0.0399(17) Uani 1 1 d . . . . .
C52 C 0.8585(7) 0.8869(4) 0.5373(3) 0.052(2) Uani 1 1 d . . . . .
H52 H 0.7797 0.9313 0.5286 0.062 Uiso 1 1 calc R U . . .
C53 C 0.9529(9) 0.9156(6) 0.5455(3) 0.070(2) Uani 1 1 d . . . . .
H53 H 0.9391 0.9796 0.5437 0.084 Uiso 1 1 calc R U . . .
C54 C 1.0680(8) 0.8517(7) 0.5562(3) 0.067(2) Uani 1 1 d . . . . .
H54 H 1.1337 0.8725 0.5604 0.080 Uiso 1 1 calc R U . . .
C55 C 1.0914(7) 0.7582(6) 0.5612(3) 0.066(2) Uani 1 1 d . . . . .
H55 H 1.1715 0.7153 0.5694 0.079 Uiso 1 1 calc R U . . .
C56 C 0.9938(7) 0.7272(5) 0.5539(3) 0.0477(19) Uani 1 1 d . . . . .
C57 C 1.0094(7) 0.6329(5) 0.5580(3) 0.062(2) Uani 1 1 d . . . . .
H57 H 1.0886 0.5879 0.5651 0.075 Uiso 1 1 calc R U . . .
C58 C 0.9127(6) 0.6046(4) 0.5520(3) 0.049(2) Uani 1 1 d . . . . .
H58 H 0.9249 0.5408 0.5560 0.058 Uiso 1 1 calc R U . . .
C59 C 0.6136(6) 0.6079(4) 0.4091(3) 0.0505(19) Uani 1 1 d . . . . .
H59A H 0.6489 0.5470 0.4315 0.061 Uiso 1 1 calc R U . . .
H59B H 0.5637 0.6009 0.3766 0.061 Uiso 1 1 calc R U . . .
C60 C 0.7203(6) 0.6333(4) 0.3786(3) 0.066(2) Uani 1 1 d . . . . .
H60A H 0.6871 0.6925 0.3552 0.099 Uiso 1 1 calc R U . . .
H60B H 0.7688 0.5854 0.3513 0.099 Uiso 1 1 calc R U . . .
H60C H 0.7728 0.6380 0.4100 0.099 Uiso 1 1 calc R U . . .
C61 C 0.4503(6) 0.7781(4) 0.4195(3) 0.0462(18) Uani 1 1 d . . . . .
H61A H 0.5117 0.8037 0.4015 0.055 Uiso 1 1 calc R U . . .
H61B H 0.4079 0.7664 0.3854 0.055 Uiso 1 1 calc R U . . .
C63 C 0.4265(6) 0.6370(4) 0.4924(3) 0.0411(17) Uani 1 1 d . . . . .
H63A H 0.4749 0.5772 0.5133 0.049 Uiso 1 1 calc R U . . .
H63B H 0.3799 0.6790 0.5242 0.049 Uiso 1 1 calc R U . . .
C70 C 0.0526(7) 0.5885(4) 0.2393(4) 0.055(2) Uani 1 1 d . . . . .
C68 C 0.1507(8) 0.6105(4) 0.3261(4) 0.066(2) Uani 1 1 d . . . . .
H68 H 0.1507 0.6173 0.3685 0.079 Uiso 1 1 calc R U . . .
C69 C 0.0524(6) 0.5995(4) 0.3016(3) 0.0512(19) Uani 1 1 d . . . . .
H69 H -0.0161 0.5993 0.3272 0.061 Uiso 1 1 calc R U . . .
C71 C -0.0538(8) 0.5798(5) 0.2125(4) 0.106(3) Uani 1 1 d . . . . .
H71A H -0.0697 0.6157 0.1733 0.159 Uiso 1 1 calc R U . . .
H71B H -0.1261 0.6031 0.2401 0.159 Uiso 1 1 calc R U . . .
H71C H -0.0368 0.5148 0.2062 0.159 Uiso 1 1 calc R U . . .
B1 B 1.2012(7) 0.3206(5) 0.0446(3) 0.043(2) Uani 1 1 d . . . . .
B2 B 0.5223(7) 0.6803(5) 0.4561(3) 0.037(2) Uani 1 1 d . . . . .
N1 N 1.3171(4) 0.1642(3) -0.1539(2) 0.0312(13) Uani 1 1 d . . . . .
N2 N 1.3143(4) 0.2974(3) -0.1331(2) 0.0307(13) Uani 1 1 d . . . . .
N5 N 0.4545(4) 0.8300(3) 0.6557(2) 0.0310(13) Uani 1 1 d . . . . .
N6 N 0.5837(4) 0.6975(3) 0.6320(2) 0.0289(12) Uani 1 1 d . . . . .
O1 O 1.3069(3) 0.2930(2) -0.00324(17) 0.0342(11) Uani 1 1 d . . . . .
O2 O 0.5960(3) 0.7061(2) 0.50252(17) 0.0319(10) 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
C32 C31 1.525(8) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C62 C61 1.536(7) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C64 C63 1.532(8) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C79A C80A 1.3900 . ?
C79A C84A 1.3900 . ?
C79A C85A 1.433(15) . ?
C80A C81A 1.3900 . ?
C80A H80A 0.9500 . ?
C81A C82A 1.3900 . ?
C81A H81A 0.9500 . ?
C82A C83A 1.3900 . ?
C82A H82A 0.9500 . ?
C83A C84A 1.3900 . ?
C83A H83A 0.9500 . ?
C84A H84A 0.9500 . ?
C85A H85A 0.9800 . ?
C85A H85B 0.9800 . ?
C85A H85C 0.9800 . ?
C79B C80B 1.3900 . ?
C79B C84B 1.3900 . ?
C79B C85B 1.408(16) . ?
C80B C81B 1.3900 . ?
C80B H80B 0.9500 . ?
C81B C82B 1.3900 . ?
C81B H81B 0.9500 . ?
C82B C83B 1.3900 . ?
C82B H82B 0.9500 . ?
C83B C84B 1.3900 . ?
C83B H83B 0.9500 . ?
C84B H84B 0.9500 . ?
C85B H85D 0.9800 . ?
C85B H85E 0.9800 . ?
C85B H85F 0.9800 . ?
C66 C67 1.358(10) . ?
C66 C65 1.359(10) . ?
C66 H66 0.9500 . ?
C67 C68 1.362(10) . ?
C67 H67 0.9500 . ?
C65 C70 1.365(9) . ?
C65 H65 0.9500 . ?
C72 C73 1.3900 . ?
C72 C77 1.3900 . ?
C72 H72 0.9500 . ?
C73 C74 1.3900 . ?
C73 H73 0.9500 . ?
C74 C75 1.3900 . ?
C74 H74 0.9500 . ?
C75 C76 1.3900 . ?
C75 H75 0.9500 . ?
C76 C77 1.3900 . ?
C76 H76 0.9500 . ?
C77 C78 1.458(13) . ?
C78 H78A 0.9800 . ?
C78 H78B 0.9800 . ?
C78 H78C 0.9800 . ?
C1 N2 1.323(6) . ?
C1 N1 1.326(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.359(7) . ?
C2 N1 1.386(7) . ?
C2 C4 1.484(8) . ?
C3 N2 1.379(7) . ?
C3 C5 1.495(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.362(9) . ?
C6 C7 1.393(8) . ?
C6 N1 1.455(7) . ?
C7 C8 1.382(9) . ?
C7 C12 1.493(9) . ?
C8 C9 1.363(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(10) . ?
C9 C13 1.537(9) . ?
C10 C11 1.398(9) . ?
C10 H10 0.9500 . ?
C11 C14 1.483(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N2 1.472(6) . ?
C15 C16 1.548(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O1 1.384(6) . ?
C16 C17 1.511(8) . ?
C16 H16 1.0000 . ?
C17 C18 1.367(7) . ?
C17 C26 1.418(8) . ?
C18 C19 1.417(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(8) . ?
C19 C24 1.415(8) . ?
C20 C21 1.372(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.419(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.413(8) . ?
C25 C26 1.351(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.511(9) . ?
C27 B1 1.652(9) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.529(8) . ?
C29 B1 1.638(9) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 B1 1.632(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C33 N6 1.320(6) . ?
C33 N5 1.322(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.355(7) . ?
C34 N6 1.382(7) . ?
C34 C36 1.493(8) . ?
C35 N5 1.371(7) . ?
C35 C37 1.504(7) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.376(8) . ?
C38 C43 1.378(8) . ?
C38 N5 1.445(7) . ?
C39 C40 1.396(8) . ?
C39 C44 1.496(8) . ?
C40 C41 1.364(9) . ?
C40 H40 0.9500 . ?
C41 C42 1.397(9) . ?
C41 C45 1.514(8) . ?
C42 C43 1.390(8) . ?
C42 H42 0.9500 . ?
C43 C46 1.503(8) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 N6 1.481(6) . ?
C47 C48 1.531(7) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 O2 1.372(6) . ?
C48 C49 1.527(8) . ?
C48 H48 1.0000 . ?
C49 C50 1.361(7) . ?
C49 C58 1.401(8) . ?
C50 C51 1.405(8) . ?
C50 H50 0.9500 . ?
C51 C56 1.410(8) . ?
C51 C52 1.416(8) . ?
C52 C53 1.364(9) . ?
C52 H52 0.9500 . ?
C53 C54 1.374(10) . ?
C53 H53 0.9500 . ?
C54 C55 1.380(9) . ?
C54 H54 0.9500 . ?
C55 C56 1.418(9) . ?
C55 H55 0.9500 . ?
C56 C57 1.411(8) . ?
C57 C58 1.376(9) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
C59 C60 1.542(8) . ?
C59 B2 1.629(8) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 B2 1.624(8) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C63 B2 1.645(9) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C70 C69 1.398(9) . ?
C70 C71 1.468(10) . ?
C68 C69 1.374(9) . ?
C68 H68 0.9500 . ?
C69 H69 0.9500 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
B1 O1 1.530(8) . ?
B2 O2 1.548(8) . ?

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
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C80A C79A C84A 120.0 . . ?
C80A C79A C85A 119.3(12) . . ?
C84A C79A C85A 120.7(12) . . ?
C79A C80A C81A 120.0 . . ?
C79A C80A H80A 120.0 . . ?
C81A C80A H80A 120.0 . . ?
C82A C81A C80A 120.0 . . ?
C82A C81A H81A 120.0 . . ?
C80A C81A H81A 120.0 . . ?
C81A C82A C83A 120.0 . . ?
C81A C82A H82A 120.0 . . ?
C83A C82A H82A 120.0 . . ?
C84A C83A C82A 120.0 . . ?
C84A C83A H83A 120.0 . . ?
C82A C83A H83A 120.0 . . ?
C83A C84A C79A 120.0 . . ?
C83A C84A H84A 120.0 . . ?
C79A C84A H84A 120.0 . . ?
C79A C85A H85A 109.5 . . ?
C79A C85A H85B 109.5 . . ?
H85A C85A H85B 109.5 . . ?
C79A C85A H85C 109.5 . . ?
H85A C85A H85C 109.5 . . ?
H85B C85A H85C 109.5 . . ?
C80B C79B C84B 120.0 . . ?
C80B C79B C85B 122.6(15) . . ?
C84B C79B C85B 117.2(15) . . ?
C81B C80B C79B 120.0 . . ?
C81B C80B H80B 120.0 . . ?
C79B C80B H80B 120.0 . . ?
C80B C81B C82B 120.0 . . ?
C80B C81B H81B 120.0 . . ?
C82B C81B H81B 120.0 . . ?
C81B C82B C83B 120.0 . . ?
C81B C82B H82B 120.0 . . ?
C83B C82B H82B 120.0 . . ?
C84B C83B C82B 120.0 . . ?
C84B C83B H83B 120.0 . . ?
C82B C83B H83B 120.0 . . ?
C83B C84B C79B 120.0 . . ?
C83B C84B H84B 120.0 . . ?
C79B C84B H84B 120.0 . . ?
C79B C85B H85D 109.5 . . ?
C79B C85B H85E 109.5 . . ?
H85D C85B H85E 109.5 . . ?
C79B C85B H85F 109.5 . . ?
H85D C85B H85F 109.5 . . ?
H85E C85B H85F 109.5 . . ?
C67 C66 C65 120.7(8) . . ?
C67 C66 H66 119.6 . . ?
C65 C66 H66 119.6 . . ?
C66 C67 C68 120.2(8) . . ?
C66 C67 H67 119.9 . . ?
C68 C67 H67 119.9 . . ?
C66 C65 C70 120.9(8) . . ?
C66 C65 H65 119.5 . . ?
C70 C65 H65 119.5 . . ?
C73 C72 C77 120.0 . . ?
C73 C72 H72 120.0 . . ?
C77 C72 H72 120.0 . . ?
C74 C73 C72 120.0 . . ?
C74 C73 H73 120.0 . . ?
C72 C73 H73 120.0 . . ?
C73 C74 C75 120.0 . . ?
C73 C74 H74 120.0 . . ?
C75 C74 H74 120.0 . . ?
C74 C75 C76 120.0 . . ?
C74 C75 H75 120.0 . . ?
C76 C75 H75 120.0 . . ?
C77 C76 C75 120.0 . . ?
C77 C76 H76 120.0 . . ?
C75 C76 H76 120.0 . . ?
C76 C77 C72 120.0 . . ?
C76 C77 C78 123.6(8) . . ?
C72 C77 C78 116.3(8) . . ?
C77 C78 H78A 109.5 . . ?
C77 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
C77 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
N2 C1 N1 108.8(5) . . ?
N2 C1 H1 125.6 . . ?
N1 C1 H1 125.6 . . ?
C3 C2 N1 106.6(5) . . ?
C3 C2 C4 131.3(6) . . ?
N1 C2 C4 122.2(5) . . ?
C2 C3 N2 106.8(5) . . ?
C2 C3 C5 130.4(6) . . ?
N2 C3 C5 122.7(5) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 124.2(6) . . ?
C11 C6 N1 118.5(6) . . ?
C7 C6 N1 117.3(6) . . ?
C8 C7 C6 116.5(7) . . ?
C8 C7 C12 121.3(7) . . ?
C6 C7 C12 122.1(6) . . ?
C9 C8 C7 122.2(8) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 118.8(7) . . ?
C8 C9 C13 120.5(9) . . ?
C10 C9 C13 120.6(9) . . ?
C9 C10 C11 122.1(7) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C6 C11 C10 116.2(7) . . ?
C6 C11 C14 122.8(6) . . ?
C10 C11 C14 121.0(7) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 111.7(4) . . ?
N2 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
O1 C16 C17 111.2(5) . . ?
O1 C16 C15 111.0(5) . . ?
C17 C16 C15 109.9(5) . . ?
O1 C16 H16 108.2 . . ?
C17 C16 H16 108.2 . . ?
C15 C16 H16 108.2 . . ?
C18 C17 C26 118.3(6) . . ?
C18 C17 C16 120.3(6) . . ?
C26 C17 C16 121.4(6) . . ?
C17 C18 C19 121.7(6) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C24 119.5(6) . . ?
C20 C19 C18 121.9(7) . . ?
C24 C19 C18 118.6(6) . . ?
C21 C20 C19 120.3(7) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.0(7) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 120.5(7) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 120.5(7) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C19 119.1(6) . . ?
C25 C24 C23 122.6(7) . . ?
C19 C24 C23 118.3(7) . . ?
C26 C25 C24 120.2(6) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C17 122.0(6) . . ?
C25 C26 H26 119.0 . . ?
C17 C26 H26 119.0 . . ?
C28 C27 B1 115.0(5) . . ?
C28 C27 H27A 108.5 . . ?
B1 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
B1 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 B1 115.3(5) . . ?
C30 C29 H29A 108.5 . . ?
B1 C29 H29A 108.5 . . ?
C30 C29 H29B 108.5 . . ?
B1 C29 H29B 108.5 . . ?
H29A C29 H29B 107.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 B1 116.0(6) . . ?
C32 C31 H31A 108.3 . . ?
B1 C31 H31A 108.3 . . ?
C32 C31 H31B 108.3 . . ?
B1 C31 H31B 108.3 . . ?
H31A C31 H31B 107.4 . . ?
N6 C33 N5 108.9(5) . . ?
N6 C33 H33 125.5 . . ?
N5 C33 H33 125.5 . . ?
C35 C34 N6 106.4(5) . . ?
C35 C34 C36 131.2(6) . . ?
N6 C34 C36 122.4(5) . . ?
C34 C35 N5 107.2(5) . . ?
C34 C35 C37 130.8(6) . . ?
N5 C35 C37 122.0(5) . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 C43 123.5(6) . . ?
C39 C38 N5 118.2(6) . . ?
C43 C38 N5 118.3(5) . . ?
C38 C39 C40 117.6(6) . . ?
C38 C39 C44 122.1(6) . . ?
C40 C39 C44 120.3(6) . . ?
C41 C40 C39 121.2(7) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C40 C41 C42 119.4(6) . . ?
C40 C41 C45 120.7(7) . . ?
C42 C41 C45 119.9(7) . . ?
C43 C42 C41 121.1(7) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C38 C43 C42 117.1(6) . . ?
C38 C43 C46 122.3(5) . . ?
C42 C43 C46 120.6(6) . . ?
C39 C44 H44A 109.5 . . ?
C39 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C39 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C41 C45 H45A 109.5 . . ?
C41 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C41 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N6 C47 C48 111.6(4) . . ?
N6 C47 H47A 109.3 . . ?
C48 C47 H47A 109.3 . . ?
N6 C47 H47B 109.3 . . ?
C48 C47 H47B 109.3 . . ?
H47A C47 H47B 108.0 . . ?
O2 C48 C49 110.8(5) . . ?
O2 C48 C47 111.0(5) . . ?
C49 C48 C47 109.6(5) . . ?
O2 C48 H48 108.5 . . ?
C49 C48 H48 108.5 . . ?
C47 C48 H48 108.5 . . ?
C50 C49 C58 120.3(6) . . ?
C50 C49 C48 120.0(6) . . ?
C58 C49 C48 119.7(5) . . ?
C49 C50 C51 120.9(6) . . ?
C49 C50 H50 119.6 . . ?
C51 C50 H50 119.6 . . ?
C50 C51 C56 119.9(6) . . ?
C50 C51 C52 121.7(7) . . ?
C56 C51 C52 118.4(6) . . ?
C53 C52 C51 121.3(7) . . ?
C53 C52 H52 119.4 . . ?
C51 C52 H52 119.4 . . ?
C52 C53 C54 119.8(7) . . ?
C52 C53 H53 120.1 . . ?
C54 C53 H53 120.1 . . ?
C53 C54 C55 122.1(7) . . ?
C53 C54 H54 119.0 . . ?
C55 C54 H54 119.0 . . ?
C54 C55 C56 118.9(7) . . ?
C54 C55 H55 120.6 . . ?
C56 C55 H55 120.6 . . ?
C51 C56 C57 117.7(7) . . ?
C51 C56 C55 119.6(7) . . ?
C57 C56 C55 122.7(7) . . ?
C58 C57 C56 121.7(7) . . ?
C58 C57 H57 119.2 . . ?
C56 C57 H57 119.2 . . ?
C57 C58 C49 119.6(6) . . ?
C57 C58 H58 120.2 . . ?
C49 C58 H58 120.2 . . ?
C60 C59 B2 116.3(5) . . ?
C60 C59 H59A 108.2 . . ?
B2 C59 H59A 108.2 . . ?
C60 C59 H59B 108.2 . . ?
B2 C59 H59B 108.2 . . ?
H59A C59 H59B 107.4 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C62 C61 B2 115.2(5) . . ?
C62 C61 H61A 108.5 . . ?
B2 C61 H61A 108.5 . . ?
C62 C61 H61B 108.5 . . ?
B2 C61 H61B 108.5 . . ?
H61A C61 H61B 107.5 . . ?
C64 C63 B2 114.9(5) . . ?
C64 C63 H63A 108.6 . . ?
B2 C63 H63A 108.6 . . ?
C64 C63 H63B 108.6 . . ?
B2 C63 H63B 108.6 . . ?
H63A C63 H63B 107.5 . . ?
C65 C70 C69 118.1(7) . . ?
C65 C70 C71 121.1(8) . . ?
C69 C70 C71 120.7(8) . . ?
C67 C68 C69 119.7(8) . . ?
C67 C68 H68 120.2 . . ?
C69 C68 H68 120.2 . . ?
C68 C69 C70 120.3(7) . . ?
C68 C69 H69 119.8 . . ?
C70 C69 H69 119.8 . . ?
C70 C71 H71A 109.5 . . ?
C70 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C70 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
O1 B1 C31 109.9(5) . . ?
O1 B1 C29 104.1(5) . . ?
C31 B1 C29 111.2(6) . . ?
O1 B1 C27 110.9(5) . . ?
C31 B1 C27 110.3(5) . . ?
C29 B1 C27 110.2(6) . . ?
O2 B2 C61 103.4(5) . . ?
O2 B2 C59 111.1(5) . . ?
C61 B2 C59 109.9(5) . . ?
O2 B2 C63 109.7(5) . . ?
C61 B2 C63 111.8(5) . . ?
C59 B2 C63 110.7(5) . . ?
C1 N1 C2 108.8(5) . . ?
C1 N1 C6 124.0(5) . . ?
C2 N1 C6 127.2(5) . . ?
C1 N2 C3 109.0(5) . . ?
C1 N2 C15 123.4(5) . . ?
C3 N2 C15 127.5(5) . . ?
C33 N5 C35 108.7(5) . . ?
C33 N5 C38 123.3(5) . . ?
C35 N5 C38 127.9(5) . . ?
C33 N6 C34 108.8(4) . . ?
C33 N6 C47 123.2(5) . . ?
C34 N6 C47 128.0(5) . . ?
C16 O1 B1 120.7(4) . . ?
C48 O2 B2 120.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C84A_b C79A_b C80A_b C81A_b 0.0 . . . . ?
C85A C79A C80A C81A -178.8(18) . . . . ?
C79A C80A C81A C82A 0.0 . . . . ?
C80A C81A C82A C83A 0.0 . . . . ?
C81A C82A C83A C84A 0.0 . . . . ?
C82A C83A C84A C79A 0.0 . . . . ?
C80A C79A C84A C83A 0.0 . . . . ?
C85A C79A C84A C83A 178.8(19) . . . . ?
C84B C79B C80B C81B 0.0 . . . . ?
C85B C79B C80B C81B 176(2) . . . . ?
C79B C80B C81B C82B 0.0 . . . . ?
C80B C81B C82B C83B 0.0 . . . . ?
C81B C82B C83B C84B 0.0 . . . . ?
C82B C83B C84B C79B 0.0 . . . . ?
C80B C79B C84B C83B 0.0 . . . . ?
C85B C79B C84B C83B -176(2) . . . . ?
C65 C66 C67 C68 -0.8(12) . . . . ?
C67 C66 C65 C70 1.1(12) . . . . ?
C77 C72 C73 C74 0.0 . . . . ?
C72 C73 C74 C75 0.0 . . . . ?
C73 C74 C75 C76 0.0 . . . . ?
C74 C75 C76 C77 0.0 . . . . ?
C75 C76 C77 C72 0.0 . . . . ?
C75 C76 C77 C78 -176.9(8) . . . . ?
C73 C72 C77 C76 0.0 . . . . ?
C73 C72 C77 C78 177.1(7) . . . . ?
N1 C2 C3 N2 -0.5(7) . . . . ?
C4 C2 C3 N2 179.4(6) . . . . ?
N1 C2 C3 C5 179.8(6) . . . . ?
C4 C2 C3 C5 -0.2(12) . . . . ?
C11 C6 C7 C8 0.2(9) . . . . ?
N1 C6 C7 C8 177.5(5) . . . . ?
C11 C6 C7 C12 178.6(6) . . . . ?
N1 C6 C7 C12 -4.2(9) . . . . ?
C6 C7 C8 C9 -2.0(10) . . . . ?
C12 C7 C8 C9 179.6(7) . . . . ?
C7 C8 C9 C10 2.6(11) . . . . ?
C7 C8 C9 C13 -175.9(6) . . . . ?
C8 C9 C10 C11 -1.4(11) . . . . ?
C13 C9 C10 C11 177.1(6) . . . . ?
C7 C6 C11 C10 0.9(9) . . . . ?
N1 C6 C11 C10 -176.3(5) . . . . ?
C7 C6 C11 C14 179.8(6) . . . . ?
N1 C6 C11 C14 2.6(9) . . . . ?
C9 C10 C11 C6 -0.3(10) . . . . ?
C9 C10 C11 C14 -179.2(6) . . . . ?
N2 C15 C16 O1 -53.7(6) . . . . ?
N2 C15 C16 C17 69.9(6) . . . . ?
O1 C16 C17 C18 23.9(7) . . . . ?
C15 C16 C17 C18 -99.5(6) . . . . ?
O1 C16 C17 C26 -156.4(5) . . . . ?
C15 C16 C17 C26 80.2(6) . . . . ?
C26 C17 C18 C19 0.1(9) . . . . ?
C16 C17 C18 C19 179.8(5) . . . . ?
C17 C18 C19 C20 -179.4(6) . . . . ?
C17 C18 C19 C24 1.0(9) . . . . ?
C24 C19 C20 C21 1.0(10) . . . . ?
C18 C19 C20 C21 -178.7(6) . . . . ?
C19 C20 C21 C22 -1.9(10) . . . . ?
C20 C21 C22 C23 2.4(12) . . . . ?
C21 C22 C23 C24 -2.1(11) . . . . ?
C20 C19 C24 C25 179.7(6) . . . . ?
C18 C19 C24 C25 -0.6(9) . . . . ?
C20 C19 C24 C23 -0.7(9) . . . . ?
C18 C19 C24 C23 179.0(6) . . . . ?
C22 C23 C24 C25 -179.2(7) . . . . ?
C22 C23 C24 C19 1.2(10) . . . . ?
C19 C24 C25 C26 -0.9(10) . . . . ?
C23 C24 C25 C26 179.5(6) . . . . ?
C24 C25 C26 C17 2.0(10) . . . . ?
C18 C17 C26 C25 -1.6(9) . . . . ?
C16 C17 C26 C25 178.7(6) . . . . ?
N6 C34 C35 N5 -1.6(6) . . . . ?
C36 C34 C35 N5 179.9(6) . . . . ?
N6 C34 C35 C37 179.9(6) . . . . ?
C36 C34 C35 C37 1.4(11) . . . . ?
C43 C38 C39 C40 -2.0(9) . . . . ?
N5 C38 C39 C40 177.2(5) . . . . ?
C43 C38 C39 C44 -180.0(6) . . . . ?
N5 C38 C39 C44 -0.7(9) . . . . ?
C38 C39 C40 C41 -0.3(9) . . . . ?
C44 C39 C40 C41 177.7(6) . . . . ?
C39 C40 C41 C42 2.6(10) . . . . ?
C39 C40 C41 C45 -178.4(6) . . . . ?
C40 C41 C42 C43 -2.7(10) . . . . ?
C45 C41 C42 C43 178.2(6) . . . . ?
C39 C38 C43 C42 1.9(9) . . . . ?
N5 C38 C43 C42 -177.3(5) . . . . ?
C39 C38 C43 C46 -178.5(6) . . . . ?
N5 C38 C43 C46 2.2(9) . . . . ?
C41 C42 C43 C38 0.5(9) . . . . ?
C41 C42 C43 C46 -179.0(6) . . . . ?
N6 C47 C48 O2 -54.6(6) . . . . ?
N6 C47 C48 C49 68.2(6) . . . . ?
O2 C48 C49 C50 21.0(7) . . . . ?
C47 C48 C49 C50 -101.8(6) . . . . ?
O2 C48 C49 C58 -159.8(5) . . . . ?
C47 C48 C49 C58 77.4(6) . . . . ?
C58 C49 C50 C51 -0.4(9) . . . . ?
C48 C49 C50 C51 178.9(5) . . . . ?
C49 C50 C51 C56 0.1(9) . . . . ?
C49 C50 C51 C52 -178.8(5) . . . . ?
C50 C51 C52 C53 178.4(6) . . . . ?
C56 C51 C52 C53 -0.6(10) . . . . ?
C51 C52 C53 C54 1.9(11) . . . . ?
C52 C53 C54 C55 -2.3(12) . . . . ?
C53 C54 C55 C56 1.2(11) . . . . ?
C50 C51 C56 C57 0.9(9) . . . . ?
C52 C51 C56 C57 179.9(6) . . . . ?
C50 C51 C56 C55 -179.5(6) . . . . ?
C52 C51 C56 C55 -0.5(9) . . . . ?
C54 C55 C56 C51 0.2(10) . . . . ?
C54 C55 C56 C57 179.8(7) . . . . ?
C51 C56 C57 C58 -1.8(10) . . . . ?
C55 C56 C57 C58 178.6(7) . . . . ?
C56 C57 C58 C49 1.7(10) . . . . ?
C50 C49 C58 C57 -0.5(9) . . . . ?
C48 C49 C58 C57 -179.8(6) . . . . ?
C66 C65 C70 C69 -0.5(10) . . . . ?
C66 C65 C70 C71 177.1(6) . . . . ?
C66 C67 C68 C69 0.0(11) . . . . ?
C67 C68 C69 C70 0.6(10) . . . . ?
C65 C70 C69 C68 -0.3(9) . . . . ?
C71 C70 C69 C68 -178.0(6) . . . . ?
C32 C31 B1 O1 170.1(5) . . . . ?
C32 C31 B1 C29 55.3(7) . . . . ?
C32 C31 B1 C27 -67.4(7) . . . . ?
C30 C29 B1 O1 -62.2(7) . . . . ?
C30 C29 B1 C31 56.2(7) . . . . ?
C30 C29 B1 C27 178.9(5) . . . . ?
C28 C27 B1 O1 -47.5(8) . . . . ?
C28 C27 B1 C31 -169.5(6) . . . . ?
C28 C27 B1 C29 67.3(7) . . . . ?
C62 C61 B2 O2 -64.6(7) . . . . ?
C62 C61 B2 C59 176.7(5) . . . . ?
C62 C61 B2 C63 53.4(7) . . . . ?
C60 C59 B2 O2 -49.3(8) . . . . ?
C60 C59 B2 C61 64.5(7) . . . . ?
C60 C59 B2 C63 -171.5(6) . . . . ?
C64 C63 B2 O2 171.5(5) . . . . ?
C64 C63 B2 C61 57.4(6) . . . . ?
C64 C63 B2 C59 -65.5(7) . . . . ?
N2 C1 N1 C2 -0.3(7) . . . . ?
N2 C1 N1 C6 -179.7(5) . . . . ?
C3 C2 N1 C1 0.5(7) . . . . ?
C4 C2 N1 C1 -179.4(6) . . . . ?
C3 C2 N1 C6 179.9(6) . . . . ?
C4 C2 N1 C6 0.0(9) . . . . ?
C11 C6 N1 C1 88.1(7) . . . . ?
C7 C6 N1 C1 -89.3(7) . . . . ?
C11 C6 N1 C2 -91.2(7) . . . . ?
C7 C6 N1 C2 91.4(7) . . . . ?
N1 C1 N2 C3 0.0(7) . . . . ?
N1 C1 N2 C15 -179.9(5) . . . . ?
C2 C3 N2 C1 0.3(7) . . . . ?
C5 C3 N2 C1 -180.0(6) . . . . ?
C2 C3 N2 C15 -179.7(5) . . . . ?
C5 C3 N2 C15 -0.1(9) . . . . ?
C16 C15 N2 C1 63.1(7) . . . . ?
C16 C15 N2 C3 -116.8(6) . . . . ?
N6 C33 N5 C35 -0.6(6) . . . . ?
N6 C33 N5 C38 176.1(5) . . . . ?
C34 C35 N5 C33 1.4(7) . . . . ?
C37 C35 N5 C33 -179.9(5) . . . . ?
C34 C35 N5 C38 -175.2(5) . . . . ?
C37 C35 N5 C38 3.6(9) . . . . ?
C39 C38 N5 C33 -92.8(7) . . . . ?
C43 C38 N5 C33 86.4(7) . . . . ?
C39 C38 N5 C35 83.3(7) . . . . ?
C43 C38 N5 C35 -97.5(7) . . . . ?
N5 C33 N6 C34 -0.4(6) . . . . ?
N5 C33 N6 C47 -178.1(4) . . . . ?
C35 C34 N6 C33 1.2(6) . . . . ?
C36 C34 N6 C33 179.9(5) . . . . ?
C35 C34 N6 C47 178.8(5) . . . . ?
C36 C34 N6 C47 -2.6(9) . . . . ?
C48 C47 N6 C33 65.7(7) . . . . ?
C48 C47 N6 C34 -111.5(6) . . . . ?
C17 C16 O1 B1 138.3(5) . . . . ?
C15 C16 O1 B1 -98.9(6) . . . . ?
C31 B1 O1 C16 75.1(7) . . . . ?
C29 B1 O1 C16 -165.6(5) . . . . ?
C27 B1 O1 C16 -47.1(7) . . . . ?
C49 C48 O2 B2 141.2(5) . . . . ?
C47 C48 O2 B2 -96.8(6) . . . . ?
C61 B2 O2 C48 -166.2(5) . . . . ?
C59 B2 O2 C48 -48.4(7) . . . . ?
C63 B2 O2 C48 74.3(6) . . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 1003571'
#######################################################################
#
#                 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_LBEt2Mes

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C30 H37 B N2 O), (C4 H8 O), 1/3(C6 H6)'
_chemical_formula_sum            'C36 H47 B N2 O2'
_chemical_formula_weight         550.58

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      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                   9.9318(3)
_cell_length_b                   27.3125(10)
_cell_length_c                   10.7984(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.301(3)
_cell_angle_gamma                90
_cell_volume                     2881.99(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4267
_cell_measurement_theta_min      2.9409
_cell_measurement_theta_max      27.4238

_exptl_crystal_description       'colourless block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             1196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5525
_exptl_crystal_size_mid          0.1319
_exptl_crystal_size_min          0.0984
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.83803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_reflns_number            33866
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.947
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6592
_reflns_number_gt                4727
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'Sir 92'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'POV Ray'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0792P)²+1.3429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6592
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1775
_refine_ls_wR_factor_gt          0.1615
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.85294(14) 0.20005(5) 0.22952(12) 0.0260(3) Uani 1 1 d . . . . .
N2 N 0.62834(16) 0.10826(6) 0.37195(14) 0.0245(4) Uani 1 1 d . . . . .
N1 N 0.78890(17) 0.15743(6) 0.44852(15) 0.0256(4) Uani 1 1 d . . . . .
C19 C 1.1973(2) 0.29087(7) 0.27445(18) 0.0256(4) Uani 1 1 d . . . . .
C16 C 0.8725(2) 0.22732(7) 0.34053(17) 0.0227(4) Uani 1 1 d . . . . .
H16 H 0.7881 0.2470 0.3430 0.027 Uiso 1 1 calc R U . . .
C26 C 1.0120(2) 0.29906(7) 0.44073(18) 0.0264(4) Uani 1 1 d . . . . .
H26 H 0.9491 0.3018 0.4971 0.032 Uiso 1 1 calc R U . . .
C17 C 0.99322(19) 0.26196(7) 0.34730(17) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.71330(19) 0.14283(7) 0.33890(18) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.3877(2) 0.10300(8) 0.27470(18) 0.0268(4) Uani 1 1 d . . . . .
C29 C 0.5885(2) 0.19864(8) 0.15031(18) 0.0278(4) Uani 1 1 d . . . . .
H29A H 0.5114 0.1754 0.1284 0.033 Uiso 1 1 calc R U . . .
H29B H 0.5680 0.2200 0.2187 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4365(2) 0.01475(8) 0.1612(2) 0.0336(5) Uani 1 1 d . . . . .
H8 H 0.4531 -0.0152 0.1215 0.040 Uiso 1 1 calc R U . . .
C3 C 0.6527(2) 0.10140(8) 0.50261(18) 0.0292(5) Uani 1 1 d . . . . .
C6 C 0.51898(19) 0.08329(7) 0.28978(17) 0.0227(4) Uani 1 1 d . . . . .
C20 C 1.2931(2) 0.28806(9) 0.1914(2) 0.0337(5) Uani 1 1 d . . . . .
H20 H 1.2825 0.2637 0.1275 0.040 Uiso 1 1 calc R U . . .
C23 C 1.3277(2) 0.36064(9) 0.3772(2) 0.0372(5) Uani 1 1 d . . . . .
H23 H 1.3400 0.3855 0.4396 0.045 Uiso 1 1 calc R U . . .
C18 C 1.0848(2) 0.25820(7) 0.26707(18) 0.0245(4) Uani 1 1 d . . . . .
H18 H 1.0729 0.2332 0.2050 0.029 Uiso 1 1 calc R U . . .
C24 C 1.2155(2) 0.32798(8) 0.36852(18) 0.0274(4) Uani 1 1 d . . . . .
C15 C 0.8990(2) 0.19403(8) 0.45577(18) 0.0277(4) Uani 1 1 d . . . . .
H15A H 0.9880 0.1772 0.4600 0.033 Uiso 1 1 calc R U . . .
H15B H 0.9033 0.2139 0.5331 0.033 Uiso 1 1 calc R U . . .
C27 C 0.7620(2) 0.12616(8) 0.10449(19) 0.0290(5) Uani 1 1 d . . . . .
H27A H 0.6923 0.0999 0.0980 0.035 Uiso 1 1 calc R U . . .
H27B H 0.7557 0.1411 0.0201 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3054(2) 0.03348(9) 0.14199(19) 0.0353(5) Uani 1 1 d . . . . .
C2 C 0.7530(2) 0.13270(8) 0.55068(19) 0.0319(5) Uani 1 1 d . . . . .
C5 C 0.5768(3) 0.06428(9) 0.5646(2) 0.0418(6) Uani 1 1 d . . . . .
H5A H 0.6118 0.0642 0.6554 0.063 Uiso 1 1 calc R U . . .
H5B H 0.5896 0.0318 0.5299 0.063 Uiso 1 1 calc R U . . .
H5C H 0.4791 0.0725 0.5493 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3568(2) 0.14996(8) 0.3380(2) 0.0385(5) Uani 1 1 d . . . . .
H14A H 0.2651 0.1615 0.3004 0.058 Uiso 1 1 calc R U . . .
H14B H 0.4246 0.1749 0.3266 0.058 Uiso 1 1 calc R U . . .
H14C H 0.3607 0.1440 0.4281 0.058 Uiso 1 1 calc R U . . .
C25 C 1.1194(2) 0.33087(8) 0.45072(19) 0.0303(5) Uani 1 1 d . . . . .
H25 H 1.1299 0.3554 0.5140 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2821(2) 0.07725(9) 0.20007(19) 0.0323(5) Uani 1 1 d . . . . .
H10 H 0.1917 0.0900 0.1886 0.039 Uiso 1 1 calc R U . . .
C21 C 1.4006(2) 0.32016(9) 0.2030(2) 0.0410(6) Uani 1 1 d . . . . .
H21 H 1.4640 0.3178 0.1470 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5453(2) 0.03846(7) 0.23709(19) 0.0272(4) Uani 1 1 d . . . . .
C30 C 0.5969(3) 0.23048(9) 0.0348(2) 0.0398(6) Uani 1 1 d . . . . .
H30A H 0.6669 0.2558 0.0577 0.060 Uiso 1 1 calc R U . . .
H30B H 0.5081 0.2460 0.0052 0.060 Uiso 1 1 calc R U . . .
H30C H 0.6211 0.2099 -0.0324 0.060 Uiso 1 1 calc R U . . .
C28 C 0.9040(2) 0.10352(9) 0.1438(2) 0.0395(6) Uani 1 1 d . . . . .
H28A H 0.9733 0.1295 0.1541 0.059 Uiso 1 1 calc R U . . .
H28B H 0.9215 0.0805 0.0789 0.059 Uiso 1 1 calc R U . . .
H28C H 0.9082 0.0861 0.2237 0.059 Uiso 1 1 calc R U . . .
C4 C 0.8157(3) 0.14386(10) 0.6841(2) 0.0499(7) Uani 1 1 d . . . . .
H4A H 0.7899 0.1770 0.7054 0.075 Uiso 1 1 calc R U . . .
H4B H 0.9155 0.1416 0.6942 0.075 Uiso 1 1 calc R U . . .
H4C H 0.7828 0.1202 0.7402 0.075 Uiso 1 1 calc R U . . .
C22 C 1.4183(2) 0.35656(9) 0.2965(2) 0.0417(6) Uani 1 1 d . . . . .
H22 H 1.4937 0.3784 0.3036 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1880(3) 0.00665(13) 0.0605(3) 0.0639(9) Uani 1 1 d . . . . .
H13A H 0.1123 0.0030 0.1068 0.096 Uiso 1 1 calc R U . . .
H13B H 0.2191 -0.0258 0.0386 0.096 Uiso 1 1 calc R U . . .
H13C H 0.1569 0.0254 -0.0167 0.096 Uiso 1 1 calc R U . . .
B1 B 0.7280(2) 0.16765(8) 0.2026(2) 0.0234(5) Uani 1 1 d . . . . .
C12 C 0.6841(2) 0.01478(9) 0.2642(2) 0.0413(6) Uani 1 1 d . . . . .
H12A H 0.7435 0.0298 0.2116 0.062 Uiso 1 1 calc R U . . .
H12B H 0.6750 -0.0203 0.2456 0.062 Uiso 1 1 calc R U . . .
H12C H 0.7242 0.0194 0.3532 0.062 Uiso 1 1 calc 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
O1 C16 1.395(2) . ?
O1 B1 1.510(2) . ?
N2 C1 1.356(2) . ?
N2 C3 1.401(2) . ?
N2 C6 1.445(2) . ?
N1 C1 1.344(2) . ?
N1 C2 1.393(3) . ?
N1 C15 1.473(2) . ?
C19 C18 1.421(3) . ?
C19 C20 1.421(3) . ?
C19 C24 1.423(3) . ?
C16 C17 1.519(3) . ?
C16 C15 1.526(3) . ?
C16 H16 1.0000 . ?
C26 C25 1.365(3) . ?
C26 C17 1.418(3) . ?
C26 H26 0.9500 . ?
C17 C18 1.368(3) . ?
C1 B1 1.650(3) . ?
C11 C10 1.393(3) . ?
C11 C6 1.393(3) . ?
C11 C14 1.510(3) . ?
C29 C30 1.535(3) . ?
C29 B1 1.636(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C8 C9 1.380(3) . ?
C8 C7 1.394(3) . ?
C8 H8 0.9500 . ?
C3 C2 1.344(3) . ?
C3 C5 1.492(3) . ?
C6 C7 1.395(3) . ?
C20 C21 1.370(3) . ?
C20 H20 0.9500 . ?
C23 C22 1.364(3) . ?
C23 C24 1.418(3) . ?
C23 H23 0.9500 . ?
C18 H18 0.9500 . ?
C24 C25 1.417(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C27 C28 1.529(3) . ?
C27 B1 1.628(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C9 C10 1.389(3) . ?
C9 C13 1.518(3) . ?
C2 C4 1.495(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C25 H25 0.9500 . ?
C10 H10 0.9500 . ?
C21 C22 1.406(4) . ?
C21 H21 0.9500 . ?
C7 C12 1.503(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C22 H22 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 B1 117.49(14) . . ?
C1 N2 C3 110.78(16) . . ?
C1 N2 C6 127.00(16) . . ?
C3 N2 C6 122.07(16) . . ?
C1 N1 C2 111.82(16) . . ?
C1 N1 C15 122.73(16) . . ?
C2 N1 C15 125.42(16) . . ?
C18 C19 C20 122.62(19) . . ?
C18 C19 C24 119.02(18) . . ?
C20 C19 C24 118.37(19) . . ?
O1 C16 C17 111.17(15) . . ?
O1 C16 C15 111.09(16) . . ?
C17 C16 C15 108.19(15) . . ?
O1 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C15 C16 H16 108.8 . . ?
C25 C26 C17 120.84(18) . . ?
C25 C26 H26 119.6 . . ?
C17 C26 H26 119.6 . . ?
C18 C17 C26 119.11(18) . . ?
C18 C17 C16 122.11(17) . . ?
C26 C17 C16 118.79(17) . . ?
N1 C1 N2 104.52(16) . . ?
N1 C1 B1 122.62(16) . . ?
N2 C1 B1 132.78(17) . . ?
C10 C11 C6 117.70(19) . . ?
C10 C11 C14 119.83(19) . . ?
C6 C11 C14 122.46(19) . . ?
C30 C29 B1 114.06(17) . . ?
C30 C29 H29A 108.7 . . ?
B1 C29 H29A 108.7 . . ?
C30 C29 H29B 108.7 . . ?
B1 C29 H29B 108.7 . . ?
H29A C29 H29B 107.6 . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C2 C3 N2 106.64(17) . . ?
C2 C3 C5 131.13(19) . . ?
N2 C3 C5 122.21(18) . . ?
C7 C6 C11 122.11(18) . . ?
C7 C6 N2 119.32(17) . . ?
C11 C6 N2 118.34(17) . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C17 C18 C19 121.51(18) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C25 C24 C23 122.23(19) . . ?
C25 C24 C19 118.24(18) . . ?
C23 C24 C19 119.53(19) . . ?
N1 C15 C16 110.05(15) . . ?
N1 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N1 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C28 C27 B1 112.91(17) . . ?
C28 C27 H27A 109.0 . . ?
B1 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
B1 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C8 C9 C10 118.73(19) . . ?
C8 C9 C13 121.0(2) . . ?
C10 C9 C13 120.3(2) . . ?
C3 C2 N1 106.23(17) . . ?
C3 C2 C4 130.8(2) . . ?
N1 C2 C4 122.85(19) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26 C25 C24 121.29(19) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C8 C7 C6 117.75(19) . . ?
C8 C7 C12 120.14(19) . . ?
C6 C7 C12 122.06(19) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 B1 C27 105.91(16) . . ?
O1 B1 C29 112.30(17) . . ?
C27 B1 C29 113.40(16) . . ?
O1 B1 C1 105.66(15) . . ?
C27 B1 C1 110.88(17) . . ?
C29 B1 C1 108.43(15) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 O1 C16 C17 -173.89(16) . . . . ?
B1 O1 C16 C15 65.6(2) . . . . ?
C25 C26 C17 C18 0.3(3) . . . . ?
C25 C26 C17 C16 179.71(18) . . . . ?
O1 C16 C17 C18 -12.8(3) . . . . ?
C15 C16 C17 C18 109.5(2) . . . . ?
O1 C16 C17 C26 167.87(16) . . . . ?
C15 C16 C17 C26 -69.9(2) . . . . ?
C2 N1 C1 N2 -0.1(2) . . . . ?
C15 N1 C1 N2 177.88(17) . . . . ?
C2 N1 C1 B1 176.96(18) . . . . ?
C15 N1 C1 B1 -5.0(3) . . . . ?
C3 N2 C1 N1 -0.4(2) . . . . ?
C6 N2 C1 N1 175.17(18) . . . . ?
C3 N2 C1 B1 -177.0(2) . . . . ?
C6 N2 C1 B1 -1.5(3) . . . . ?
C1 N2 C3 C2 0.8(2) . . . . ?
C6 N2 C3 C2 -175.05(18) . . . . ?
C1 N2 C3 C5 -177.9(2) . . . . ?
C6 N2 C3 C5 6.3(3) . . . . ?
C10 C11 C6 C7 -2.5(3) . . . . ?
C14 C11 C6 C7 176.13(19) . . . . ?
C10 C11 C6 N2 -176.93(17) . . . . ?
C14 C11 C6 N2 1.7(3) . . . . ?
C1 N2 C6 C7 93.2(2) . . . . ?
C3 N2 C6 C7 -91.7(2) . . . . ?
C1 N2 C6 C11 -92.3(2) . . . . ?
C3 N2 C6 C11 82.8(2) . . . . ?
C18 C19 C20 C21 -179.5(2) . . . . ?
C24 C19 C20 C21 0.5(3) . . . . ?
C26 C17 C18 C19 -0.7(3) . . . . ?
C16 C17 C18 C19 179.98(17) . . . . ?
C20 C19 C18 C17 -179.34(19) . . . . ?
C24 C19 C18 C17 0.7(3) . . . . ?
C22 C23 C24 C25 179.8(2) . . . . ?
C22 C23 C24 C19 -0.3(3) . . . . ?
C18 C19 C24 C25 -0.4(3) . . . . ?
C20 C19 C24 C25 179.66(19) . . . . ?
C18 C19 C24 C23 179.69(19) . . . . ?
C20 C19 C24 C23 -0.3(3) . . . . ?
C1 N1 C15 C16 25.3(3) . . . . ?
C2 N1 C15 C16 -157.01(19) . . . . ?
O1 C16 C15 N1 -53.7(2) . . . . ?
C17 C16 C15 N1 -175.97(16) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C7 C8 C9 C13 -179.1(2) . . . . ?
N2 C3 C2 N1 -0.8(2) . . . . ?
C5 C3 C2 N1 177.7(2) . . . . ?
N2 C3 C2 C4 176.0(3) . . . . ?
C5 C3 C2 C4 -5.5(5) . . . . ?
C1 N1 C2 C3 0.6(3) . . . . ?
C15 N1 C2 C3 -177.34(19) . . . . ?
C1 N1 C2 C4 -176.5(2) . . . . ?
C15 N1 C2 C4 5.5(3) . . . . ?
C17 C26 C25 C24 0.0(3) . . . . ?
C23 C24 C25 C26 180.0(2) . . . . ?
C19 C24 C25 C26 0.0(3) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C13 C9 C10 C11 -179.5(2) . . . . ?
C6 C11 C10 C9 -0.1(3) . . . . ?
C14 C11 C10 C9 -178.8(2) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C9 C8 C7 C6 -2.6(3) . . . . ?
C9 C8 C7 C12 174.9(2) . . . . ?
C11 C6 C7 C8 3.9(3) . . . . ?
N2 C6 C7 C8 178.19(17) . . . . ?
C11 C6 C7 C12 -173.6(2) . . . . ?
N2 C6 C7 C12 0.7(3) . . . . ?
C24 C23 C22 C21 0.6(4) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C16 O1 B1 C27 -158.08(16) . . . . ?
C16 O1 B1 C29 77.6(2) . . . . ?
C16 O1 B1 C1 -40.4(2) . . . . ?
C28 C27 B1 O1 46.6(2) . . . . ?
C28 C27 B1 C29 170.18(18) . . . . ?
C28 C27 B1 C1 -67.6(2) . . . . ?
C30 C29 B1 O1 54.3(2) . . . . ?
C30 C29 B1 C27 -65.7(2) . . . . ?
C30 C29 B1 C1 170.68(18) . . . . ?
N1 C1 B1 O1 9.6(3) . . . . ?
N2 C1 B1 O1 -174.21(19) . . . . ?
N1 C1 B1 C27 124.0(2) . . . . ?
N2 C1 B1 C27 -59.9(3) . . . . ?
N1 C1 B1 C29 -110.9(2) . . . . ?
N2 C1 B1 C29 65.2(3) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.059

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 196 27 ' '
2 0.000 0.500 0.000 196 27 ' '
_platon_squeeze_details          
;
;


_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 1003572'
#######################################################################
#
#                 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_LBEt2tBu

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H33 B N2 O'
_chemical_formula_weight         292.26

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'
O O 0.0106 0.0060 '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 1 21/c 1'

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

_cell_length_a                   12.9028(5)
_cell_length_b                   11.8814(4)
_cell_length_c                   12.6969(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.000(3)
_cell_angle_gamma                90.00
_cell_volume                     1888.66(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3830
_cell_measurement_theta_min      3.2480
_cell_measurement_theta_max      27.8121

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5259
_exptl_crystal_size_mid          0.2293
_exptl_crystal_size_min          0.1328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18205
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         27.87
_reflns_number_total             4488
_reflns_number_gt                3150
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'MERCURY 2012'

_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 > 2σ(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)+(0.0550P)²+0.5732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4488
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.51674(16) 0.34486(17) 0.56737(15) 0.0518(5) Uani 1 1 d . . .
H1A H 0.4577 0.3612 0.5046 0.078 Uiso 1 1 calc R . .
H1B H 0.5470 0.2709 0.5581 0.078 Uiso 1 1 calc R . .
H1C H 0.5721 0.4026 0.5734 0.078 Uiso 1 1 calc R . .
C2 C 0.57001(17) 0.3267(2) 0.76846(17) 0.0624(6) Uani 1 1 d . . .
H2A H 0.6242 0.3845 0.7686 0.094 Uiso 1 1 calc R . .
H2B H 0.6009 0.2521 0.7636 0.094 Uiso 1 1 calc R . .
H2C H 0.5456 0.3319 0.8356 0.094 Uiso 1 1 calc R . .
C3 C 0.42337(17) 0.45815(16) 0.68107(16) 0.0526(5) Uani 1 1 d . . .
H3A H 0.4060 0.4631 0.7519 0.079 Uiso 1 1 calc R . .
H3B H 0.3578 0.4656 0.6233 0.079 Uiso 1 1 calc R . .
H3C H 0.4730 0.5187 0.6745 0.079 Uiso 1 1 calc R . .
C4 C 0.47521(14) 0.34468(15) 0.67093(13) 0.0390(4) Uani 1 1 d . . .
C5 C 0.39636(13) 0.24618(13) 0.66329(12) 0.0337(4) Uani 1 1 d . . .
H5 H 0.4373 0.1746 0.6637 0.040 Uiso 1 1 calc R . .
C6 C 0.34440(15) 0.24263(14) 0.75922(12) 0.0391(4) Uani 1 1 d . . .
H6A H 0.4002 0.2401 0.8282 0.047 Uiso 1 1 calc R . .
H6B H 0.3006 0.3110 0.7595 0.047 Uiso 1 1 calc R . .
C7 C 0.24530(13) 0.09154(14) 0.83046(12) 0.0361(4) Uani 1 1 d . . .
H7 H 0.2645 0.1132 0.9047 0.043 Uiso 1 1 calc R . .
C8 C 0.17366(13) 0.00420(14) 0.67795(12) 0.0353(4) Uani 1 1 d . . .
H8 H 0.1325 -0.0481 0.6284 0.042 Uiso 1 1 calc R . .
C9 C 0.12171(14) -0.06930(15) 0.84814(14) 0.0420(4) Uani 1 1 d . . .
C10 C 0.17561(17) -0.06733(18) 0.96899(14) 0.0544(5) Uani 1 1 d . . .
H10A H 0.2491 -0.0948 0.9804 0.082 Uiso 1 1 calc R . .
H10B H 0.1360 -0.1158 1.0080 0.082 Uiso 1 1 calc R . .
H10C H 0.1764 0.0099 0.9963 0.082 Uiso 1 1 calc R . .
C11 C 0.00794(15) -0.02336(19) 0.82662(16) 0.0556(5) Uani 1 1 d . . .
H11A H 0.0095 0.0534 0.8553 0.083 Uiso 1 1 calc R . .
H11B H -0.0348 -0.0715 0.8625 0.083 Uiso 1 1 calc R . .
H11C H -0.0239 -0.0225 0.7483 0.083 Uiso 1 1 calc R . .
C12 C 0.12265(19) -0.18800(17) 0.80374(17) 0.0598(6) Uani 1 1 d . . .
H12A H 0.0849 -0.1889 0.7269 0.090 Uiso 1 1 calc R . .
H12B H 0.0870 -0.2391 0.8443 0.090 Uiso 1 1 calc R . .
H12C H 0.1966 -0.2125 0.8114 0.090 Uiso 1 1 calc R . .
C13 C 0.23323(13) 0.08921(13) 0.65108(12) 0.0312(3) Uani 1 1 d . . .
C14 C 0.14317(14) 0.16110(15) 0.45333(13) 0.0397(4) Uani 1 1 d . . .
H14A H 0.1565 0.1953 0.3867 0.048 Uiso 1 1 calc R . .
H14B H 0.1066 0.0883 0.4327 0.048 Uiso 1 1 calc R . .
C15 C 0.06929(17) 0.23774(18) 0.49702(17) 0.0577(5) Uani 1 1 d . . .
H15A H 0.0485 0.2006 0.5577 0.087 Uiso 1 1 calc R . .
H15B H 0.0054 0.2538 0.4394 0.087 Uiso 1 1 calc R . .
H15C H 0.1063 0.3084 0.5222 0.087 Uiso 1 1 calc R . .
C16 C 0.33191(15) 0.04940(15) 0.48999(13) 0.0429(4) Uani 1 1 d . . .
H16A H 0.3559 0.0876 0.4307 0.052 Uiso 1 1 calc R . .
H16B H 0.3964 0.0331 0.5483 0.052 Uiso 1 1 calc R . .
C17 C 0.28112(19) -0.06209(17) 0.44666(18) 0.0638(6) Uani 1 1 d . . .
H17A H 0.2569 -0.1014 0.5042 0.096 Uiso 1 1 calc R . .
H17B H 0.3338 -0.1086 0.4226 0.096 Uiso 1 1 calc R . .
H17C H 0.2200 -0.0481 0.3853 0.096 Uiso 1 1 calc R . .
N1 N 0.27665(11) 0.14187(11) 0.74936(10) 0.0333(3) Uani 1 1 d . . .
N2 N 0.18246(11) 0.00575(11) 0.78909(10) 0.0351(3) Uani 1 1 d . . .
O1 O 0.31455(9) 0.24885(9) 0.56644(8) 0.0323(3) Uani 1 1 d . . .
B1 B 0.25716(15) 0.13731(15) 0.53798(13) 0.0312(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C4 1.535(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.530(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.538(2) . ?
C5 O1 1.4140(18) . ?
C5 C6 1.526(2) . ?
C5 H5 1.0000 . ?
C6 N1 1.470(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.329(2) . ?
C7 N1 1.3353(19) . ?
C7 H7 0.9500 . ?
C8 C13 1.362(2) . ?
C8 N2 1.3881(19) . ?
C8 H8 0.9500 . ?
C9 N2 1.502(2) . ?
C9 C12 1.520(3) . ?
C9 C10 1.524(3) . ?
C9 C11 1.528(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.3872(19) . ?
C13 B1 1.643(2) . ?
C14 C15 1.517(3) . ?
C14 B1 1.623(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.521(3) . ?
C16 B1 1.636(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O1 B1 1.519(2) . ?

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
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C3 C4 C2 109.65(16) . . ?
C3 C4 C1 108.80(14) . . ?
C2 C4 C1 108.48(16) . . ?
C3 C4 C5 112.41(15) . . ?
C2 C4 C5 109.38(14) . . ?
C1 C4 C5 108.03(13) . . ?
O1 C5 C6 108.36(13) . . ?
O1 C5 C4 112.39(12) . . ?
C6 C5 C4 112.46(13) . . ?
O1 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C4 C5 H5 107.8 . . ?
N1 C6 C5 108.75(12) . . ?
N1 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
N1 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 N1 107.96(13) . . ?
N2 C7 H7 126.0 . . ?
N1 C7 H7 126.0 . . ?
C13 C8 N2 109.43(14) . . ?
C13 C8 H8 125.3 . . ?
N2 C8 H8 125.3 . . ?
N2 C9 C12 108.29(14) . . ?
N2 C9 C10 109.10(14) . . ?
C12 C9 C10 110.18(16) . . ?
N2 C9 C11 107.08(14) . . ?
C12 C9 C11 111.03(17) . . ?
C10 C9 C11 111.06(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 N1 103.81(13) . . ?
C8 C13 B1 135.56(14) . . ?
N1 C13 B1 120.60(13) . . ?
C15 C14 B1 114.29(14) . . ?
C15 C14 H14A 108.7 . . ?
B1 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
B1 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
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 . . ?
C17 C16 B1 116.71(16) . . ?
C17 C16 H16A 108.1 . . ?
B1 C16 H16A 108.1 . . ?
C17 C16 H16B 108.1 . . ?
B1 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 N1 C13 111.10(13) . . ?
C7 N1 C6 125.73(13) . . ?
C13 N1 C6 123.13(12) . . ?
C7 N2 C8 107.69(13) . . ?
C7 N2 C9 126.89(13) . . ?
C8 N2 C9 125.12(14) . . ?
C5 O1 B1 113.94(11) . . ?
O1 B1 C14 108.50(13) . . ?
O1 B1 C16 110.38(13) . . ?
C14 B1 C16 112.71(13) . . ?
O1 B1 C13 106.24(12) . . ?
C14 B1 C13 107.92(13) . . ?
C16 B1 C13 110.84(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C5 O1 66.40(17) . . . . ?
C2 C4 C5 O1 -171.55(15) . . . . ?
C1 C4 C5 O1 -53.66(18) . . . . ?
C3 C4 C5 C6 -56.22(18) . . . . ?
C2 C4 C5 C6 65.8(2) . . . . ?
C1 C4 C5 C6 -176.27(15) . . . . ?
O1 C5 C6 N1 59.17(17) . . . . ?
C4 C5 C6 N1 -175.97(14) . . . . ?
N2 C8 C13 N1 -0.61(17) . . . . ?
N2 C8 C13 B1 -178.49(16) . . . . ?
N2 C7 N1 C13 0.46(19) . . . . ?
N2 C7 N1 C6 178.04(15) . . . . ?
C8 C13 N1 C7 0.10(18) . . . . ?
B1 C13 N1 C7 178.38(14) . . . . ?
C8 C13 N1 C6 -177.56(15) . . . . ?
B1 C13 N1 C6 0.7(2) . . . . ?
C5 C6 N1 C7 158.14(15) . . . . ?
C5 C6 N1 C13 -24.6(2) . . . . ?
N1 C7 N2 C8 -0.82(18) . . . . ?
N1 C7 N2 C9 -174.80(15) . . . . ?
C13 C8 N2 C7 0.91(19) . . . . ?
C13 C8 N2 C9 175.02(15) . . . . ?
C12 C9 N2 C7 -143.57(18) . . . . ?
C10 C9 N2 C7 -23.6(2) . . . . ?
C11 C9 N2 C7 96.64(19) . . . . ?
C12 C9 N2 C8 43.4(2) . . . . ?
C10 C9 N2 C8 163.38(16) . . . . ?
C11 C9 N2 C8 -76.3(2) . . . . ?
C6 C5 O1 B1 -73.59(16) . . . . ?
C4 C5 O1 B1 161.51(13) . . . . ?
C5 O1 B1 C14 160.59(12) . . . . ?
C5 O1 B1 C16 -75.46(15) . . . . ?
C5 O1 B1 C13 44.78(16) . . . . ?
C15 C14 B1 O1 -60.32(19) . . . . ?
C15 C14 B1 C16 177.12(16) . . . . ?
C15 C14 B1 C13 54.39(19) . . . . ?
C17 C16 B1 O1 -173.82(14) . . . . ?
C17 C16 B1 C14 -52.3(2) . . . . ?
C17 C16 B1 C13 68.75(19) . . . . ?
C8 C13 B1 O1 169.24(17) . . . . ?
N1 C13 B1 O1 -8.37(19) . . . . ?
C8 C13 B1 C14 53.0(2) . . . . ?
N1 C13 B1 C14 -124.57(15) . . . . ?
C8 C13 B1 C16 -70.8(2) . . . . ?
N1 C13 B1 C16 111.56(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 1003573'
#######################################################################
#
#                 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_Et3BImtBu

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H27 B N2'
_chemical_formula_weight         222.18

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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

_cell_length_a                   10.7950(4)
_cell_length_b                   10.2921(4)
_cell_length_c                   13.4612(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.670(3)
_cell_angle_gamma                90.00
_cell_volume                     1482.20(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2825
_cell_measurement_theta_min      3.0102
_cell_measurement_theta_max      27.4248

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.9756
_exptl_crystal_size_mid          0.2279
_exptl_crystal_size_min          0.0534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18430
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.1120
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3390
_reflns_number_gt                2501
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ortep
_computing_publication_material  mercury

_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 > 2σ(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)+(0.0543P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3390
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
C1 C -0.18329(13) -0.08350(15) 0.14807(11) 0.0306(3) Uani 1 1 d . . .
C2 C -0.16671(16) -0.20632(16) 0.21098(13) 0.0390(4) Uani 1 1 d . . .
H2A H -0.0848 -0.2446 0.2055 0.059 Uiso 1 1 calc R . .
H2B H -0.2326 -0.2686 0.1868 0.059 Uiso 1 1 calc R . .
H2C H -0.1721 -0.1849 0.2812 0.059 Uiso 1 1 calc R . .
C3 C -0.16850(19) -0.1136(2) 0.03945(13) 0.0506(5) Uani 1 1 d . . .
H3A H -0.1791 -0.0337 -0.0003 0.076 Uiso 1 1 calc R . .
H3B H -0.2319 -0.1771 0.0125 0.076 Uiso 1 1 calc R . .
H3C H -0.0850 -0.1494 0.0363 0.076 Uiso 1 1 calc R . .
C4 C 0.00936(13) -0.00105(14) 0.26253(10) 0.0266(3) Uani 1 1 d . . .
H4 H 0.0246 -0.0776 0.3017 0.032 Uiso 1 1 calc R . .
C5 C -0.07369(15) 0.13635(16) 0.14899(12) 0.0369(4) Uani 1 1 d . . .
H5 H -0.1264 0.1745 0.0946 0.044 Uiso 1 1 calc R . .
C6 C 0.02532(15) 0.19274(16) 0.20384(11) 0.0363(4) Uani 1 1 d . . .
H6 H 0.0545 0.2784 0.1946 0.044 Uiso 1 1 calc R . .
C7 C 0.13989(14) 0.25289(17) 0.43005(12) 0.0354(4) Uani 1 1 d . . .
H7A H 0.2093 0.2835 0.4802 0.042 Uiso 1 1 calc R . .
H7B H 0.1129 0.3272 0.3857 0.042 Uiso 1 1 calc R . .
C8 C 0.03088(16) 0.2133(2) 0.48515(13) 0.0471(5) Uani 1 1 d . . .
H8A H 0.0054 0.2877 0.5231 0.071 Uiso 1 1 calc R . .
H8B H 0.0569 0.1418 0.5313 0.071 Uiso 1 1 calc R . .
H8C H -0.0396 0.1852 0.4364 0.071 Uiso 1 1 calc R . .
C9 C 0.22987(15) 0.00632(16) 0.42513(12) 0.0361(4) Uani 1 1 d . . .
H9A H 0.1534 -0.0312 0.4468 0.043 Uiso 1 1 calc R . .
H9B H 0.2631 -0.0574 0.3803 0.043 Uiso 1 1 calc R . .
C10 C 0.32735(17) 0.0283(2) 0.51758(14) 0.0498(5) Uani 1 1 d . . .
H10A H 0.3461 -0.0546 0.5522 0.075 Uiso 1 1 calc R . .
H10B H 0.2942 0.0897 0.5631 0.075 Uiso 1 1 calc R . .
H10C H 0.4039 0.0638 0.4965 0.075 Uiso 1 1 calc R . .
C11 C 0.30637(14) 0.19419(16) 0.30548(12) 0.0343(4) Uani 1 1 d . . .
H11A H 0.2756 0.2712 0.2655 0.041 Uiso 1 1 calc R . .
H11B H 0.3751 0.2236 0.3567 0.041 Uiso 1 1 calc R . .
C12 C 0.35991(17) 0.0977(2) 0.23609(14) 0.0518(5) Uani 1 1 d . . .
H12A H 0.4269 0.1396 0.2053 0.078 Uiso 1 1 calc R . .
H12B H 0.2936 0.0696 0.1836 0.078 Uiso 1 1 calc R . .
H12C H 0.3935 0.0221 0.2749 0.078 Uiso 1 1 calc R . .
C13 C -0.31027(15) -0.02241(18) 0.15662(15) 0.0448(4) Uani 1 1 d . . .
H13A H -0.3202 0.0568 0.1160 0.067 Uiso 1 1 calc R . .
H13B H -0.3154 -0.0008 0.2268 0.067 Uiso 1 1 calc R . .
H13C H -0.3767 -0.0841 0.1325 0.067 Uiso 1 1 calc R . .
N1 N -0.08415(11) 0.01296(12) 0.18664(8) 0.0274(3) Uani 1 1 d . . .
N2 N 0.07740(11) 0.10629(12) 0.27537(8) 0.0273(3) Uani 1 1 d . . .
B1 B 0.19327(15) 0.13958(17) 0.36273(12) 0.0277(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.5008(18) . ?
C1 C2 1.519(2) . ?
C1 C3 1.524(2) . ?
C1 C13 1.526(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N2 1.3252(18) . ?
C4 N1 1.3447(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.347(2) . ?
C5 N1 1.3776(19) . ?
C5 H5 0.9500 . ?
C6 N2 1.3749(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.528(2) . ?
C7 B1 1.629(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.535(2) . ?
C9 B1 1.629(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.529(2) . ?
C11 B1 1.628(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N2 B1 1.6346(19) . ?

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
N1 C1 C2 109.40(11) . . ?
N1 C1 C3 107.77(13) . . ?
C2 C1 C3 110.24(14) . . ?
N1 C1 C13 107.92(13) . . ?
C2 C1 C13 109.94(14) . . ?
C3 C1 C13 111.49(14) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 N1 110.88(12) . . ?
N2 C4 H4 124.6 . . ?
N1 C4 H4 124.6 . . ?
C6 C5 N1 107.07(13) . . ?
C6 C5 H5 126.5 . . ?
N1 C5 H5 126.5 . . ?
C5 C6 N2 109.00(14) . . ?
C5 C6 H6 125.5 . . ?
N2 C6 H6 125.5 . . ?
C8 C7 B1 115.60(14) . . ?
C8 C7 H7A 108.4 . . ?
B1 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
B1 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 B1 112.76(13) . . ?
C10 C9 H9A 109.0 . . ?
B1 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
B1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 B1 115.69(14) . . ?
C12 C11 H11A 108.4 . . ?
B1 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
B1 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 N1 C5 106.76(12) . . ?
C4 N1 C1 128.33(12) . . ?
C5 N1 C1 124.91(12) . . ?
C4 N2 C6 106.29(12) . . ?
C4 N2 B1 128.76(12) . . ?
C6 N2 B1 124.77(12) . . ?
C11 B1 C7 111.07(13) . . ?
C11 B1 C9 112.89(13) . . ?
C7 B1 C9 113.29(13) . . ?
C11 B1 N2 106.38(11) . . ?
C7 B1 N2 104.88(12) . . ?
C9 B1 N2 107.70(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C6 N2 0.12(19) . . . . ?
N2 C4 N1 C5 0.45(17) . . . . ?
N2 C4 N1 C1 -179.16(13) . . . . ?
C6 C5 N1 C4 -0.35(18) . . . . ?
C6 C5 N1 C1 179.29(14) . . . . ?
C2 C1 N1 C4 1.6(2) . . . . ?
C3 C1 N1 C4 -118.26(17) . . . . ?
C13 C1 N1 C4 121.21(16) . . . . ?
C2 C1 N1 C5 -177.94(14) . . . . ?
C3 C1 N1 C5 62.19(19) . . . . ?
C13 C1 N1 C5 -58.34(19) . . . . ?
N1 C4 N2 C6 -0.38(17) . . . . ?
N1 C4 N2 B1 174.90(13) . . . . ?
C5 C6 N2 C4 0.15(18) . . . . ?
C5 C6 N2 B1 -175.37(14) . . . . ?
C12 C11 B1 C7 -177.32(14) . . . . ?
C12 C11 B1 C9 54.18(18) . . . . ?
C12 C11 B1 N2 -63.74(17) . . . . ?
C8 C7 B1 C11 178.49(13) . . . . ?
C8 C7 B1 C9 -53.22(17) . . . . ?
C8 C7 B1 N2 63.97(16) . . . . ?
C10 C9 B1 C11 69.77(18) . . . . ?
C10 C9 B1 C7 -57.57(18) . . . . ?
C10 C9 B1 N2 -173.09(13) . . . . ?
C4 N2 B1 C11 130.63(15) . . . . ?
C6 N2 B1 C11 -54.90(19) . . . . ?
C4 N2 B1 C7 -111.62(16) . . . . ?
C6 N2 B1 C7 62.86(18) . . . . ?
C4 N2 B1 C9 9.3(2) . . . . ?
C6 N2 B1 C9 -176.19(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 1003574'
#######################################################################
#
#                 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_LSatBEt3

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C0 C24 H41 B N2 O'
_chemical_formula_weight         384.40

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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.2340(19)
_cell_length_b                   11.811(3)
_cell_length_c                   12.577(3)
_cell_angle_alpha                69.63(2)
_cell_angle_beta                 70.562(19)
_cell_angle_gamma                76.389(19)
_cell_volume                     1201.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    669
_cell_measurement_theta_min      3.7350
_cell_measurement_theta_max      28.2640

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6576
_exptl_crystal_size_mid          0.2535
_exptl_crystal_size_min          0.0871
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.40354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1042
_diffrn_reflns_number            4846
_diffrn_reflns_av_unetI/netI     0.1219
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.338
_diffrn_reflns_theta_max         29.749
_diffrn_reflns_theta_full        22.500
_diffrn_measured_fraction_theta_max 0.507
_diffrn_measured_fraction_theta_full 0.640
_diffrn_reflns_Laue_measured_fraction_max 0.507
_diffrn_reflns_Laue_measured_fraction_full 0.640
_diffrn_reflns_point_group_measured_fraction_max 0.507
_diffrn_reflns_point_group_measured_fraction_full 0.640
_reflns_number_total             3474
_reflns_number_gt                1921
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  POV-RAY

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1810P)²+0.1334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3474
_refine_ls_number_parameters     262
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.1020
_refine_ls_wR_factor_ref         0.3345
_refine_ls_wR_factor_gt          0.2788
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.072
_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
C1 C 0.8050(4) 0.2624(4) 0.7256(4) 0.0228(11) Uani 1 1 d . . . . .
C2 C 0.9911(5) 0.3641(5) 0.7302(6) 0.0419(15) Uani 1 1 d . . . . .
H2A H 0.9897 0.4092 0.7839 0.050 Uiso 1 1 calc R U . . .
H2B H 1.0642 0.3959 0.6522 0.050 Uiso 1 1 calc R U . . .
C3 C 1.0313(5) 0.2289(5) 0.7811(6) 0.0495(17) Uani 1 1 d . . . . .
H3A H 1.1402 0.2006 0.7439 0.059 Uiso 1 1 calc R U . . .
H3B H 1.0142 0.2060 0.8675 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7429(5) 0.4868(4) 0.6952(4) 0.0305(12) Uani 1 1 d . . . . .
H4A H 0.6489 0.4771 0.6796 0.037 Uiso 1 1 calc R U . . .
H4B H 0.8019 0.5423 0.6226 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6941(5) 0.5448(4) 0.7944(5) 0.0288(12) Uani 1 1 d . . . . .
C6 C 0.6136(5) 0.6725(5) 0.7736(5) 0.0387(11) Uani 1 1 d . U . . .
C10 C 0.9314(4) 0.0473(4) 0.7926(4) 0.0257(11) Uani 1 1 d . . . . .
C11 C 0.8440(5) -0.0106(5) 0.9059(5) 0.0323(13) Uani 1 1 d . . . . .
C12 C 0.8649(5) -0.1361(5) 0.9440(5) 0.0405(14) Uani 1 1 d . . . . .
H12 H 0.8030 -0.1768 1.0190 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9747(5) -0.2058(4) 0.8755(5) 0.0354(13) Uani 1 1 d . . . . .
C14 C 1.0593(5) -0.1457(4) 0.7669(5) 0.0329(13) Uani 1 1 d . . . . .
H14 H 1.1342 -0.1918 0.7196 0.039 Uiso 1 1 calc R U . . .
C15 C 1.0400(5) -0.0192(4) 0.7227(4) 0.0275(12) Uani 1 1 d . . . . .
C16 C 0.7292(6) 0.0624(5) 0.9839(5) 0.0513(17) Uani 1 1 d . . . . .
H16A H 0.6700 0.0071 1.0549 0.077 Uiso 1 1 calc R U . . .
H16B H 0.6581 0.1202 0.9407 0.077 Uiso 1 1 calc R U . . .
H16C H 0.7852 0.1072 1.0066 0.077 Uiso 1 1 calc R U . . .
C17 C 1.0008(7) -0.3434(5) 0.9236(6) 0.0561(18) Uani 1 1 d . . . . .
H17A H 1.0806 -0.3676 0.9656 0.084 Uiso 1 1 calc R U . . .
H17B H 1.0347 -0.3792 0.8582 0.084 Uiso 1 1 calc R U . . .
H17C H 0.9039 -0.3725 0.9780 0.084 Uiso 1 1 calc R U . . .
C18 C 1.1336(6) 0.0427(5) 0.6000(5) 0.0418(15) Uani 1 1 d . . . . .
H18A H 1.0667 0.1099 0.5602 0.063 Uiso 1 1 calc R U . . .
H18B H 1.1758 -0.0164 0.5549 0.063 Uiso 1 1 calc R U . . .
H18C H 1.2188 0.0747 0.6053 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4952(4) 0.2961(4) 0.7812(4) 0.0323(13) Uani 1 1 d . . . . .
H19A H 0.4510 0.2225 0.8390 0.039 Uiso 1 1 calc R U . . .
H19B H 0.5258 0.3372 0.8253 0.039 Uiso 1 1 calc R U . . .
C20 C 0.3687(5) 0.3804(5) 0.7305(6) 0.0448(15) Uani 1 1 d . . . . .
H20A H 0.4072 0.4571 0.6782 0.067 Uiso 1 1 calc R U . . .
H20B H 0.2795 0.3970 0.7947 0.067 Uiso 1 1 calc R U . . .
H20C H 0.3371 0.3420 0.6856 0.067 Uiso 1 1 calc R U . . .
C21 C 0.6765(5) 0.3389(4) 0.5494(4) 0.0329(13) Uani 1 1 d . . . . .
H21A H 0.5995 0.3239 0.5185 0.039 Uiso 1 1 calc R U . . .
H21B H 0.6523 0.4250 0.5499 0.039 Uiso 1 1 calc R U . . .
C22 C 0.8386(7) 0.3210(5) 0.4643(5) 0.0494(16) Uani 1 1 d . . . . .
H22A H 0.9167 0.3329 0.4950 0.074 Uiso 1 1 calc R U . . .
H22B H 0.8420 0.3804 0.3866 0.074 Uiso 1 1 calc R U . . .
H22C H 0.8602 0.2383 0.4570 0.074 Uiso 1 1 calc R U . . .
C23 C 0.6528(5) 0.1109(4) 0.6910(5) 0.0334(13) Uani 1 1 d . . . . .
H23A H 0.7507 0.0837 0.6378 0.040 Uiso 1 1 calc R U . . .
H23B H 0.6480 0.0568 0.7721 0.040 Uiso 1 1 calc R U . . .
C24 C 0.5169(6) 0.0976(5) 0.6552(6) 0.0450(15) Uani 1 1 d . . . . .
H24A H 0.4193 0.1232 0.7082 0.068 Uiso 1 1 calc R U . . .
H24B H 0.5212 0.0122 0.6603 0.068 Uiso 1 1 calc R U . . .
H24C H 0.5226 0.1487 0.5739 0.068 Uiso 1 1 calc R U . . .
N1 N 0.8359(4) 0.3706(4) 0.7201(4) 0.0339(12) Uani 1 1 d . . . . .
N2 N 0.9221(4) 0.1786(3) 0.7516(4) 0.0294(11) Uani 1 1 d . . . . .
O1 O 0.7228(5) 0.4873(4) 0.8873(4) 0.0528(12) Uani 1 1 d . . . . .
B1 B 0.6556(5) 0.2506(5) 0.6869(5) 0.0249(12) Uani 1 1 d . . . . .
C7 C 0.7383(9) 0.7575(7) 0.6943(8) 0.081(2) Uani 1 1 d . U . . .
H7A H 0.7736 0.7482 0.6148 0.122 Uiso 1 1 calc R U . . .
H7B H 0.8264 0.7356 0.7279 0.122 Uiso 1 1 calc R U . . .
H7C H 0.6936 0.8423 0.6902 0.122 Uiso 1 1 calc R U . . .
C8 C 0.5554(10) 0.7116(8) 0.8883(8) 0.092(2) Uani 1 1 d . U . . .
H8A H 0.4935 0.7923 0.8737 0.139 Uiso 1 1 calc R U . . .
H8B H 0.6445 0.7148 0.9125 0.139 Uiso 1 1 calc R U . . .
H8C H 0.4915 0.6524 0.9510 0.139 Uiso 1 1 calc R U . . .
C9 C 0.4888(12) 0.6987(9) 0.7197(10) 0.116(3) Uani 1 1 d . U . . .
H9A H 0.5320 0.7073 0.6352 0.174 Uiso 1 1 calc R U . . .
H9B H 0.4241 0.7747 0.7306 0.174 Uiso 1 1 calc R U . . .
H9C H 0.4257 0.6318 0.7568 0.174 Uiso 1 1 calc 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
C1 N2 1.328(6) . ?
C1 N1 1.347(4) . ?
C1 B1 1.657(6) . ?
C2 N1 1.463(5) . ?
C2 C3 1.505(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.479(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.430(6) . ?
C4 C5 1.519(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O1 1.211(7) . ?
C5 C6 1.491(7) . ?
C6 C9 1.445(12) . ?
C6 C7 1.552(7) . ?
C6 C8 1.554(9) . ?
C10 C15 1.385(6) . ?
C10 C11 1.403(6) . ?
C10 N2 1.445(5) . ?
C11 C12 1.377(7) . ?
C11 C16 1.516(6) . ?
C12 C13 1.402(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.362(7) . ?
C13 C17 1.515(7) . ?
C14 C15 1.391(6) . ?
C14 H14 0.9500 . ?
C15 C18 1.513(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.506(7) . ?
C19 B1 1.670(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.541(6) . ?
C21 B1 1.652(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.525(6) . ?
C23 B1 1.638(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 107.7(4) . . ?
N2 C1 B1 129.6(3) . . ?
N1 C1 B1 122.2(4) . . ?
N1 C2 C3 101.1(3) . . ?
N1 C2 H2A 111.6 . . ?
C3 C2 H2A 111.6 . . ?
N1 C2 H2B 111.6 . . ?
C3 C2 H2B 111.6 . . ?
H2A C2 H2B 109.4 . . ?
N2 C3 C2 102.4(4) . . ?
N2 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
N2 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
N1 C4 C5 113.5(4) . . ?
N1 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 C6 121.8(4) . . ?
O1 C5 C4 119.5(5) . . ?
C6 C5 C4 118.6(5) . . ?
C9 C6 C5 115.3(5) . . ?
C9 C6 C7 109.5(7) . . ?
C5 C6 C7 107.2(4) . . ?
C9 C6 C8 109.9(6) . . ?
C5 C6 C8 111.6(6) . . ?
C7 C6 C8 102.5(5) . . ?
C15 C10 C11 121.2(4) . . ?
C15 C10 N2 118.4(4) . . ?
C11 C10 N2 120.1(4) . . ?
C12 C11 C10 117.9(4) . . ?
C12 C11 C16 121.0(4) . . ?
C10 C11 C16 121.1(5) . . ?
C11 C12 C13 122.1(4) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C13 C12 118.0(5) . . ?
C14 C13 C17 121.6(4) . . ?
C12 C13 C17 120.4(5) . . ?
C13 C14 C15 122.3(4) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C10 C15 C14 118.5(4) . . ?
C10 C15 C18 121.4(4) . . ?
C14 C15 C18 120.1(4) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 B1 117.4(4) . . ?
C20 C19 H19A 107.9 . . ?
B1 C19 H19A 107.9 . . ?
C20 C19 H19B 107.9 . . ?
B1 C19 H19B 107.9 . . ?
H19A C19 H19B 107.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 B1 115.3(5) . . ?
C22 C21 H21A 108.5 . . ?
B1 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
B1 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 B1 113.5(4) . . ?
C24 C23 H23A 108.9 . . ?
B1 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
B1 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C4 127.9(4) . . ?
C1 N1 C2 112.8(4) . . ?
C4 N1 C2 119.0(3) . . ?
C1 N2 C10 129.6(3) . . ?
C1 N2 C3 111.6(3) . . ?
C10 N2 C3 115.1(4) . . ?
C23 B1 C21 108.7(4) . . ?
C23 B1 C1 112.4(4) . . ?
C21 B1 C1 106.0(3) . . ?
C23 B1 C19 109.7(3) . . ?
C21 B1 C19 113.0(4) . . ?
C1 B1 C19 107.1(3) . . ?
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 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 19.7(5) . . . . ?
N1 C4 C5 O1 -6.6(5) . . . . ?
N1 C4 C5 C6 172.5(3) . . . . ?
O1 C5 C6 C9 -133.9(6) . . . . ?
C4 C5 C6 C9 47.0(6) . . . . ?
O1 C5 C6 C7 103.9(6) . . . . ?
C4 C5 C6 C7 -75.2(6) . . . . ?
O1 C5 C6 C8 -7.5(6) . . . . ?
C4 C5 C6 C8 173.4(4) . . . . ?
C15 C10 C11 C12 -2.5(7) . . . . ?
N2 C10 C11 C12 -175.6(4) . . . . ?
C15 C10 C11 C16 177.9(5) . . . . ?
N2 C10 C11 C16 4.8(7) . . . . ?
C10 C11 C12 C13 3.0(7) . . . . ?
C16 C11 C12 C13 -177.4(5) . . . . ?
C11 C12 C13 C14 -1.7(8) . . . . ?
C11 C12 C13 C17 176.3(5) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C17 C13 C14 C15 -178.1(5) . . . . ?
C11 C10 C15 C14 0.8(7) . . . . ?
N2 C10 C15 C14 174.0(4) . . . . ?
C11 C10 C15 C18 179.4(4) . . . . ?
N2 C10 C15 C18 -7.4(6) . . . . ?
C13 C14 C15 C10 0.5(7) . . . . ?
C13 C14 C15 C18 -178.1(5) . . . . ?
N2 C1 N1 C4 -179.7(4) . . . . ?
B1 C1 N1 C4 7.6(7) . . . . ?
N2 C1 N1 C2 6.7(5) . . . . ?
B1 C1 N1 C2 -166.0(4) . . . . ?
C5 C4 N1 C1 119.9(5) . . . . ?
C5 C4 N1 C2 -66.9(5) . . . . ?
C3 C2 N1 C1 -17.4(5) . . . . ?
C3 C2 N1 C4 168.4(4) . . . . ?
N1 C1 N2 C10 164.8(4) . . . . ?
B1 C1 N2 C10 -23.2(8) . . . . ?
N1 C1 N2 C3 7.8(6) . . . . ?
B1 C1 N2 C3 179.7(5) . . . . ?
C15 C10 N2 C1 118.2(5) . . . . ?
C11 C10 N2 C1 -68.5(6) . . . . ?
C15 C10 N2 C3 -85.4(5) . . . . ?
C11 C10 N2 C3 87.9(5) . . . . ?
C2 C3 N2 C1 -18.1(6) . . . . ?
C2 C3 N2 C10 -178.8(3) . . . . ?
C24 C23 B1 C21 -62.7(5) . . . . ?
C24 C23 B1 C1 -179.7(4) . . . . ?
C24 C23 B1 C19 61.3(5) . . . . ?
C22 C21 B1 C23 -72.1(4) . . . . ?
C22 C21 B1 C1 48.9(5) . . . . ?
C22 C21 B1 C19 165.9(3) . . . . ?
N2 C1 B1 C23 4.2(7) . . . . ?
N1 C1 B1 C23 175.1(4) . . . . ?
N2 C1 B1 C21 -114.4(5) . . . . ?
N1 C1 B1 C21 56.5(5) . . . . ?
N2 C1 B1 C19 124.7(5) . . . . ?
N1 C1 B1 C19 -64.4(5) . . . . ?
C20 C19 B1 C23 -102.5(5) . . . . ?
C20 C19 B1 C21 18.9(5) . . . . ?
C20 C19 B1 C1 135.3(4) . . . . ?

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 1003575'
#######################################################################
#
#                 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_LnsatBEt3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H39 B N2 O'
_chemical_formula_weight         454.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic

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

_cell_length_a                   8.1720(4)
_cell_length_b                   8.6088(3)
_cell_length_c                   20.0510(8)
_cell_angle_alpha                81.502(3)
_cell_angle_beta                 84.547(4)
_cell_angle_gamma                68.047(4)
_cell_volume                     1292.75(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7177
_cell_measurement_theta_min      3.4850
_cell_measurement_theta_max      29.1350

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.7199
_exptl_crystal_size_mid          0.4830
_exptl_crystal_size_min          0.1416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87789
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20429
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4734
_reflns_number_gt                3576
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    MERCURY
_computing_publication_material  POVRAY

_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 > 2σ(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)+(0.1516P)²+2.2263P] 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         4734
_refine_ls_number_parameters     313
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2740
_refine_ls_wR_factor_gt          0.2534
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
C1 C 0.0165(4) 0.0748(4) 0.76618(14) 0.0237(6) Uani 1 1 d . . .
C2 C -0.1421(5) 0.3665(4) 0.75349(17) 0.0366(8) Uani 1 1 d . . .
H2A H -0.1322 0.4436 0.7836 0.044 Uiso 1 1 calc R . .
H2B H -0.2581 0.4177 0.7324 0.044 Uiso 1 1 calc R . .
C3 C 0.0071(5) 0.3282(4) 0.70066(18) 0.0400(8) Uani 1 1 d . . .
H3A H -0.0378 0.3648 0.6546 0.048 Uiso 1 1 calc R . .
H3B H 0.0905 0.3833 0.7068 0.048 Uiso 1 1 calc R . .
C4 C 0.2451(5) 0.0585(4) 0.67290(16) 0.0347(8) Uani 1 1 d . . .
H4A H 0.3096 -0.0536 0.6975 0.042 Uiso 1 1 calc R . .
H4B H 0.3240 0.1236 0.6671 0.042 Uiso 1 1 calc R . .
C5 C 0.2040(6) 0.0351(5) 0.60441(19) 0.0448(9) Uani 1 1 d . . .
C6 C 0.3216(7) -0.1265(6) 0.5069(2) 0.0625(13) Uani 1 1 d . . .
H6 H 0.2083 -0.0709 0.4886 0.075 Uiso 1 1 calc R . .
C7 C 0.3561(7) -0.0887(5) 0.56592(18) 0.0535(12) Uani 1 1 d . . .
C8 C 0.5277(6) -0.1662(5) 0.5926(2) 0.0574(11) Uani 1 1 d D . .
H8 H 0.5507 -0.1347 0.6332 0.069 Uiso 1 1 calc R . .
C9 C 0.6612(7) -0.2870(6) 0.5598(2) 0.0630(12) Uani 1 1 d . . .
H9 H 0.7758 -0.3391 0.5773 0.076 Uiso 1 1 calc RD . .
C10 C 0.6230(7) -0.3292(6) 0.5015(2) 0.0593(12) Uani 1 1 d D . .
C11 C 0.4638(6) -0.2570(5) 0.47072(18) 0.0447(9) Uani 1 1 d D . .
C12 C 0.4252(8) -0.3001(6) 0.4128(2) 0.0662(13) Uani 1 1 d . . .
H12 H 0.3124 -0.2444 0.3940 0.079 Uiso 1 1 calc RD . .
C13 C 0.5543(8) -0.4256(6) 0.3829(2) 0.0672(14) Uani 1 1 d D . .
H13 H 0.5324 -0.4574 0.3423 0.081 Uiso 1 1 calc R . .
C14 C 0.7229(7) -0.5101(5) 0.4125(2) 0.0620(13) Uani 1 1 d . . .
H14 H 0.8095 -0.5983 0.3909 0.074 Uiso 1 1 calc R . .
C15 C 0.7636(7) -0.4702(6) 0.4690(3) 0.0736(16) Uani 1 1 d . . .
H15 H 0.8760 -0.5281 0.4878 0.088 Uiso 1 1 calc R . .
C16 C 0.2939(4) -0.1696(4) 0.81983(17) 0.0336(7) Uani 1 1 d . . .
H16A H 0.3253 -0.0694 0.8040 0.040 Uiso 1 1 calc R . .
H16B H 0.2871 -0.1815 0.8698 0.040 Uiso 1 1 calc R . .
C17 C 0.4459(5) -0.3250(5) 0.7978(2) 0.0515(10) Uani 1 1 d . . .
H17A H 0.4199 -0.4267 0.8142 0.077 Uiso 1 1 calc R . .
H17B H 0.5557 -0.3337 0.8167 0.077 Uiso 1 1 calc R . .
H17C H 0.4591 -0.3138 0.7484 0.077 Uiso 1 1 calc R . .
C18 C 0.0921(5) -0.2323(4) 0.73048(17) 0.0357(8) Uani 1 1 d . . .
H18A H 0.1702 -0.2066 0.6932 0.043 Uiso 1 1 calc R . .
H18B H 0.1431 -0.3550 0.7455 0.043 Uiso 1 1 calc R . .
C19 C -0.0883(6) -0.1916(5) 0.7030(2) 0.0520(10) Uani 1 1 d . . .
H19A H -0.1699 -0.2080 0.7400 0.078 Uiso 1 1 calc R . .
H19B H -0.0779 -0.2665 0.6692 0.078 Uiso 1 1 calc R . .
H19C H -0.1335 -0.0740 0.6822 0.078 Uiso 1 1 calc R . .
C20 C -0.0264(5) -0.1791(4) 0.85773(17) 0.0348(8) Uani 1 1 d . . .
H20A H -0.0292 -0.1143 0.8950 0.042 Uiso 1 1 calc R . .
H20B H -0.1491 -0.1458 0.8438 0.042 Uiso 1 1 calc R . .
C21 C 0.0445(6) -0.3678(4) 0.8835(2) 0.0510(10) Uani 1 1 d . . .
H21A H 0.0374 -0.4321 0.8481 0.077 Uiso 1 1 calc R . .
H21B H -0.0263 -0.3894 0.9235 0.077 Uiso 1 1 calc R . .
H21C H 0.1679 -0.4027 0.8953 0.077 Uiso 1 1 calc R . .
C22 C -0.2307(4) 0.1976(3) 0.85064(15) 0.0246(6) Uani 1 1 d . . .
C23 C -0.3992(4) 0.1983(4) 0.84497(16) 0.0318(7) Uani 1 1 d . . .
C24 C -0.5108(4) 0.2143(4) 0.90247(18) 0.0377(8) Uani 1 1 d . . .
H24 H -0.6255 0.2127 0.8995 0.045 Uiso 1 1 calc R . .
C25 C -0.4607(4) 0.2325(4) 0.96349(17) 0.0379(8) Uani 1 1 d . . .
C26 C -0.2917(4) 0.2301(4) 0.96757(16) 0.0339(7) Uani 1 1 d . . .
H26 H -0.2550 0.2408 1.0097 0.041 Uiso 1 1 calc R . .
C27 C -0.1736(4) 0.2124(4) 0.91175(15) 0.0275(7) Uani 1 1 d . . .
C28 C -0.4613(5) 0.1790(6) 0.7795(2) 0.0489(10) Uani 1 1 d . . .
H28A H -0.3962 0.2191 0.7417 0.073 Uiso 1 1 calc R . .
H28B H -0.5879 0.2456 0.7764 0.073 Uiso 1 1 calc R . .
H28C H -0.4404 0.0599 0.7779 0.073 Uiso 1 1 calc R . .
C29 C -0.5881(6) 0.2553(7) 1.0244(2) 0.0614(12) Uani 1 1 d . . .
H29A H -0.6972 0.2450 1.0129 0.092 Uiso 1 1 calc R . .
H29B H -0.6153 0.3672 1.0381 0.092 Uiso 1 1 calc R . .
H29C H -0.5344 0.1685 1.0616 0.092 Uiso 1 1 calc R . .
C30 C 0.0103(4) 0.2063(4) 0.91880(18) 0.0352(8) Uani 1 1 d . . .
H30A H 0.0950 0.0916 0.9152 0.053 Uiso 1 1 calc R . .
H30B H 0.0184 0.2387 0.9629 0.053 Uiso 1 1 calc R . .
H30C H 0.0374 0.2848 0.8829 0.053 Uiso 1 1 calc R . .
B1 B 0.0932(5) -0.1303(4) 0.79384(18) 0.0279(8) Uani 1 1 d . . .
N1 N -0.1185(3) 0.1990(3) 0.79065(12) 0.0267(6) Uani 1 1 d . . .
N2 N 0.0901(4) 0.1448(3) 0.71328(13) 0.0314(6) Uani 1 1 d . . .
O1 O 0.0581(5) 0.1081(4) 0.58290(15) 0.0663(9) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.331(4) . ?
C1 N2 1.345(4) . ?
C1 B1 1.663(4) . ?
C2 N1 1.474(4) . ?
C2 C3 1.508(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.460(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N2 1.446(4) . ?
C4 C5 1.503(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O1 1.208(5) . ?
C5 C7 1.532(6) . ?
C6 C7 1.353(6) . ?
C6 C11 1.498(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.427(7) . ?
C8 C9 1.386(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.371(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(6) . ?
C10 C15 1.505(7) . ?
C11 C12 1.368(6) . ?
C12 C13 1.363(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.433(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.336(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.535(5) . ?
C16 B1 1.664(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.520(5) . ?
C18 B1 1.650(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.532(5) . ?
C20 B1 1.638(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.390(4) . ?
C22 C23 1.391(4) . ?
C22 N1 1.443(4) . ?
C23 C24 1.390(5) . ?
C23 C28 1.503(5) . ?
C24 C25 1.374(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(5) . ?
C25 C29 1.513(5) . ?
C26 C27 1.394(4) . ?
C26 H26 0.9500 . ?
C27 C30 1.504(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 107.3(3) . . ?
N1 C1 B1 129.2(3) . . ?
N2 C1 B1 123.5(2) . . ?
N1 C2 C3 103.1(2) . . ?
N1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
N1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
N2 C3 C2 102.4(2) . . ?
N2 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
N2 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
N2 C4 C5 113.6(3) . . ?
N2 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 C4 120.9(3) . . ?
O1 C5 C7 123.4(4) . . ?
C4 C5 C7 115.7(4) . . ?
C7 C6 C11 119.4(5) . . ?
C7 C6 H6 120.3 . . ?
C11 C6 H6 120.3 . . ?
C6 C7 C8 121.0(4) . . ?
C6 C7 C5 118.0(5) . . ?
C8 C7 C5 121.0(3) . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 118.0(5) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 125.5(5) . . ?
C9 C10 C15 117.9(5) . . ?
C11 C10 C15 116.5(4) . . ?
C12 C11 C10 125.5(4) . . ?
C12 C11 C6 118.9(4) . . ?
C10 C11 C6 115.5(4) . . ?
C13 C12 C11 117.6(5) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C14 120.5(5) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 122.9(4) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C15 C10 116.9(5) . . ?
C14 C15 H15 121.6 . . ?
C10 C15 H15 121.6 . . ?
C17 C16 B1 117.9(3) . . ?
C17 C16 H16A 107.8 . . ?
B1 C16 H16A 107.8 . . ?
C17 C16 H16B 107.8 . . ?
B1 C16 H16B 107.8 . . ?
H16A C16 H16B 107.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 B1 115.3(3) . . ?
C19 C18 H18A 108.4 . . ?
B1 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
B1 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 B1 112.6(3) . . ?
C21 C20 H20A 109.1 . . ?
B1 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
B1 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 121.6(3) . . ?
C27 C22 N1 118.8(3) . . ?
C23 C22 N1 119.4(3) . . ?
C24 C23 C22 118.1(3) . . ?
C24 C23 C28 119.8(3) . . ?
C22 C23 C28 122.1(3) . . ?
C25 C24 C23 122.2(3) . . ?
C25 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C24 C25 C26 118.3(3) . . ?
C24 C25 C29 120.6(3) . . ?
C26 C25 C29 121.1(3) . . ?
C25 C26 C27 121.9(3) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C22 C27 C26 117.9(3) . . ?
C22 C27 C30 121.9(3) . . ?
C26 C27 C30 120.2(3) . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C20 B1 C18 109.4(3) . . ?
C20 B1 C1 112.5(2) . . ?
C18 B1 C1 107.5(2) . . ?
C20 B1 C16 108.7(3) . . ?
C18 B1 C16 114.0(3) . . ?
C1 B1 C16 104.8(2) . . ?
C1 N1 C22 130.5(2) . . ?
C1 N1 C2 113.2(2) . . ?
C22 N1 C2 115.9(2) . . ?
C1 N2 C4 126.7(3) . . ?
C1 N2 C3 114.0(2) . . ?
C4 N2 C3 119.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 2.2(3) . . . . ?
N2 C4 C5 O1 11.8(5) . . . . ?
N2 C4 C5 C7 -166.7(3) . . . . ?
C11 C6 C7 C8 2.6(6) . . . . ?
C11 C6 C7 C5 -175.3(3) . . . . ?
O1 C5 C7 C6 -4.6(6) . . . . ?
C4 C5 C7 C6 173.9(3) . . . . ?
O1 C5 C7 C8 177.4(4) . . . . ?
C4 C5 C7 C8 -4.1(5) . . . . ?
C6 C7 C8 C9 -2.5(6) . . . . ?
C5 C7 C8 C9 175.4(4) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C11 2.6(7) . . . . ?
C8 C9 C10 C15 -175.2(4) . . . . ?
C9 C10 C11 C12 -179.4(4) . . . . ?
C15 C10 C11 C12 -1.6(6) . . . . ?
C9 C10 C11 C6 -2.4(6) . . . . ?
C15 C10 C11 C6 175.4(3) . . . . ?
C7 C6 C11 C12 176.9(4) . . . . ?
C7 C6 C11 C10 -0.2(5) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C6 C11 C12 C13 -176.5(4) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C14 C15 C10 -0.2(6) . . . . ?
C9 C10 C15 C14 179.5(4) . . . . ?
C11 C10 C15 C14 1.5(6) . . . . ?
C27 C22 C23 C24 0.1(5) . . . . ?
N1 C22 C23 C24 -173.5(3) . . . . ?
C27 C22 C23 C28 -178.8(3) . . . . ?
N1 C22 C23 C28 7.6(5) . . . . ?
C22 C23 C24 C25 1.2(5) . . . . ?
C28 C23 C24 C25 -179.9(3) . . . . ?
C23 C24 C25 C26 -1.7(5) . . . . ?
C23 C24 C25 C29 178.0(4) . . . . ?
C24 C25 C26 C27 0.9(5) . . . . ?
C29 C25 C26 C27 -178.8(4) . . . . ?
C23 C22 C27 C26 -0.8(4) . . . . ?
N1 C22 C27 C26 172.8(3) . . . . ?
C23 C22 C27 C30 178.0(3) . . . . ?
N1 C22 C27 C30 -8.3(4) . . . . ?
C25 C26 C27 C22 0.3(5) . . . . ?
C25 C26 C27 C30 -178.6(3) . . . . ?
C21 C20 B1 C18 60.9(4) . . . . ?
C21 C20 B1 C1 -179.7(3) . . . . ?
C21 C20 B1 C16 -64.1(4) . . . . ?
C19 C18 B1 C20 61.3(4) . . . . ?
C19 C18 B1 C1 -61.0(4) . . . . ?
C19 C18 B1 C16 -176.8(3) . . . . ?
N1 C1 B1 C20 3.6(4) . . . . ?
N2 C1 B1 C20 -178.5(3) . . . . ?
N1 C1 B1 C18 124.0(3) . . . . ?
N2 C1 B1 C18 -58.0(4) . . . . ?
N1 C1 B1 C16 -114.3(3) . . . . ?
N2 C1 B1 C16 63.6(3) . . . . ?
C17 C16 B1 C20 106.0(3) . . . . ?
C17 C16 B1 C18 -16.2(4) . . . . ?
C17 C16 B1 C1 -133.5(3) . . . . ?
N2 C1 N1 C22 -173.0(3) . . . . ?
B1 C1 N1 C22 5.2(5) . . . . ?
N2 C1 N1 C2 -0.3(3) . . . . ?
B1 C1 N1 C2 177.9(3) . . . . ?
C27 C22 N1 C1 84.1(4) . . . . ?
C23 C22 N1 C1 -102.1(4) . . . . ?
C27 C22 N1 C2 -88.4(3) . . . . ?
C23 C22 N1 C2 85.4(3) . . . . ?
C3 C2 N1 C1 -1.3(4) . . . . ?
C3 C2 N1 C22 172.5(3) . . . . ?
N1 C1 N2 C4 177.3(3) . . . . ?
B1 C1 N2 C4 -1.0(5) . . . . ?
N1 C1 N2 C3 1.9(4) . . . . ?
B1 C1 N2 C3 -176.4(3) . . . . ?
C5 C4 N2 C1 105.4(4) . . . . ?
C5 C4 N2 C3 -79.4(4) . . . . ?
C2 C3 N2 C1 -2.6(4) . . . . ?
C2 C3 N2 C4 -178.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.281
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.070

# start Validation Reply Form
_vrf_DIFMX01_exp_1480            
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: Q1 appears 1.26 A from C11.
;
_vrf_PLAT097_exp_1480            
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.28 eA-3  
RESPONSE: Q1 appears 1.26 A from C11.
;

_vrf_PLAT019_HLBEt3Mes           
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.952 Why ? 
RESPONSE: Poor Quality data cut at 0.8A
;

_vrf_PLAT340_HLBEt3Mes           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0117 Ang.  
RESPONSE: Poor Quality data cut at 0.8A
;
_vrf_CHEMW03_LBEt2Mes            
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: SQUEEZE applied to remove one THF and 1/3 of a molecule of benzene. Crystal desolvated. 
;
_vrf_PLAT049_Et3BImtBu           
;
PROBLEM: Calculated Density less than 1.0 gcm-3 .........     0.9956       
RESPONSE: No large isolated Q peaks so missing solvent unlikely.
;
_vrf_PLAT027_LSatBEt3            
;
PROBLEM: _diffrn_reflns_theta_full (too) Low ............      22.50 Degree
RESPONSE: Poor quality data
;
_vrf_PLAT029_LSatBEt3            
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.640 Note  
RESPONSE: poor quality data
;
_vrf_PLAT230_LSatBEt3            
;
PROBLEM: Hirshfeld Test Diff for    C6     --  C7      ..       12.0 su    
RESPONSE: poor quality data
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 1003576'
