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

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

data_ad277_anga
_database_code_depnum_ccdc_archive 'CCDC 1042591'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
?
;
_chemical_name_common            
;
?
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H41 B Cl2 N2, 0.5(C6 H6)'

_chemical_formula_sum            'C26 H44 B Cl2 N2'
_chemical_formula_weight         466.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.7727(11)
_cell_length_b                   16.781(2)
_cell_length_c                   18.220(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.317(5)
_cell_angle_gamma                90.00
_cell_volume                     2681.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6916
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.66

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1012
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5713
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Sadabs 2008/1 (Bruker 2008)'

_exptl_special_details           
; 
 The crystal was immersed in a film of perfluoropolyether oil, mounted
on a a glass fiber and transferred to stream of cold nitrogen. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24972
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5472
_reflns_number_gt                4533
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 ver. 2010.3 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0470P)²+1.2888P] 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         5472
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.4958(2) 0.57869(12) 0.27898(10) 0.0146(4) Uani 1 1 d . . .
Cl2 Cl 0.48378(4) 0.50786(3) 0.35918(2) 0.01856(12) Uani 1 1 d . . .
Cl3 Cl 0.71262(4) 0.58624(3) 0.26202(2) 0.01791(12) Uani 1 1 d . . .
C4 C 0.47410(16) 0.67543(11) 0.30021(8) 0.0143(3) Uani 1 1 d . . .
N5 N 0.46464(15) 0.73203(9) 0.24748(7) 0.0152(3) Uani 1 1 d . . .
C6 C 0.40958(19) 0.81482(11) 0.26516(9) 0.0200(4) Uani 1 1 d . . .
H6 H 0.4075 0.8177 0.3199 0.024 Uiso 1 1 calc R . .
C7 C 0.2454(2) 0.82997(12) 0.23829(10) 0.0273(4) Uani 1 1 d . . .
H7A H 0.2431 0.8363 0.1848 0.041 Uiso 1 1 calc R . .
H7B H 0.2068 0.8786 0.2612 0.041 Uiso 1 1 calc R . .
H7C H 0.1811 0.7847 0.2517 0.041 Uiso 1 1 calc R . .
C8 C 0.5136(2) 0.88239(12) 0.24142(10) 0.0270(4) Uani 1 1 d . . .
H8A H 0.6185 0.8711 0.2578 0.040 Uiso 1 1 calc R . .
H8B H 0.4797 0.9325 0.2634 0.040 Uiso 1 1 calc R . .
H8C H 0.5094 0.8871 0.1878 0.040 Uiso 1 1 calc R . .
C9 C 0.51231(18) 0.71301(11) 0.17092(8) 0.0174(4) Uani 1 1 d . . .
H9 H 0.5212 0.6537 0.1684 0.021 Uiso 1 1 calc R . .
C10 C 0.6716(2) 0.74604(13) 0.15473(10) 0.0254(4) Uani 1 1 d . . .
H10A H 0.6632 0.8024 0.1410 0.038 Uiso 1 1 calc R . .
H10B H 0.7155 0.7159 0.1143 0.038 Uiso 1 1 calc R . .
H10C H 0.7375 0.7409 0.1986 0.038 Uiso 1 1 calc R . .
C11 C 0.3974(2) 0.73676(12) 0.11053(9) 0.0249(4) Uani 1 1 d . . .
H11A H 0.2960 0.7171 0.1229 0.037 Uiso 1 1 calc R . .
H11B H 0.4278 0.7135 0.0638 0.037 Uiso 1 1 calc R . .
H11C H 0.3946 0.7949 0.1061 0.037 Uiso 1 1 calc R . .
N12 N 0.49023(15) 0.70132(9) 0.37163(7) 0.0166(3) Uani 1 1 d . . .
C13 C 0.61575(19) 0.75948(11) 0.38986(9) 0.0206(4) Uani 1 1 d . . .
H13 H 0.6481 0.7825 0.3421 0.025 Uiso 1 1 calc R . .
C14 C 0.7550(2) 0.71559(12) 0.42208(10) 0.0254(4) Uani 1 1 d . . .
H14A H 0.7344 0.6990 0.4725 0.038 Uiso 1 1 calc R . .
H14B H 0.8435 0.7512 0.4223 0.038 Uiso 1 1 calc R . .
H14C H 0.7761 0.6685 0.3921 0.038 Uiso 1 1 calc R . .
C15 C 0.5742(2) 0.83024(12) 0.43835(10) 0.0280(4) Uani 1 1 d . . .
H15A H 0.4890 0.8596 0.4154 0.042 Uiso 1 1 calc R . .
H15B H 0.6625 0.8657 0.4440 0.042 Uiso 1 1 calc R . .
H15C H 0.5445 0.8108 0.4867 0.042 Uiso 1 1 calc R . .
C16 C 0.38496(19) 0.67015(11) 0.42791(9) 0.0189(4) Uani 1 1 d . . .
H16 H 0.3394 0.6202 0.4070 0.023 Uiso 1 1 calc R . .
C17 C 0.2521(2) 0.72780(13) 0.43900(10) 0.0266(4) Uani 1 1 d . . .
H17A H 0.2897 0.7760 0.4639 0.040 Uiso 1 1 calc R . .
H17B H 0.1750 0.7021 0.4691 0.040 Uiso 1 1 calc R . .
H17C H 0.2067 0.7422 0.3912 0.040 Uiso 1 1 calc R . .
C18 C 0.4599(2) 0.64702(12) 0.50128(9) 0.0250(4) Uani 1 1 d . . .
H18A H 0.5415 0.6084 0.4929 0.038 Uiso 1 1 calc R . .
H18B H 0.3835 0.6231 0.5329 0.038 Uiso 1 1 calc R . .
H18C H 0.5027 0.6946 0.5251 0.038 Uiso 1 1 calc R . .
C21 C 0.39648(17) 0.54180(10) 0.21095(8) 0.0142(3) Uani 1 1 d . . .
C22 C 0.45752(18) 0.48574(11) 0.16128(9) 0.0161(3) Uani 1 1 d . . .
C23 C 0.37862(18) 0.46677(11) 0.09565(9) 0.0184(4) Uani 1 1 d . . .
C24 C 0.23544(19) 0.49923(11) 0.08209(9) 0.0199(4) Uani 1 1 d . . .
H24 H 0.1852 0.4892 0.0363 0.024 Uiso 1 1 calc R . .
C25 C 0.16369(18) 0.54588(11) 0.13352(9) 0.0179(4) Uani 1 1 d . . .
C26 C 0.24357(17) 0.56647(10) 0.19868(8) 0.0153(3) Uani 1 1 d . . .
C27 C 0.60219(19) 0.43927(11) 0.17836(10) 0.0221(4) Uani 1 1 d . . .
H27A H 0.6869 0.4626 0.1516 0.033 Uiso 1 1 calc R . .
H27B H 0.5881 0.3836 0.1633 0.033 Uiso 1 1 calc R . .
H27C H 0.6251 0.4415 0.2312 0.033 Uiso 1 1 calc R . .
C28 C 0.4473(2) 0.41175(12) 0.03941(10) 0.0242(4) Uani 1 1 d . . .
H28A H 0.4545 0.3577 0.0596 0.036 Uiso 1 1 calc R . .
H28B H 0.5494 0.4307 0.0274 0.036 Uiso 1 1 calc R . .
H28C H 0.3825 0.4112 -0.0051 0.036 Uiso 1 1 calc R . .
C29 C 0.00247(18) 0.57454(13) 0.11878(9) 0.0244(4) Uani 1 1 d . . .
H29A H -0.0303 0.5591 0.0690 0.037 Uiso 1 1 calc R . .
H29B H -0.0011 0.6327 0.1233 0.037 Uiso 1 1 calc R . .
H29C H -0.0657 0.5504 0.1544 0.037 Uiso 1 1 calc R . .
C30 C 0.15485(18) 0.61123(11) 0.25595(9) 0.0187(4) Uani 1 1 d . . .
H30A H 0.1201 0.6623 0.2356 0.028 Uiso 1 1 calc R . .
H30B H 0.2206 0.6208 0.2993 0.028 Uiso 1 1 calc R . .
H30C H 0.0664 0.5795 0.2700 0.028 Uiso 1 1 calc R . .
C41 C 0.1566(2) 0.49320(12) 0.50331(11) 0.0275(4) Uani 1 1 d . . .
H41 H 0.2646 0.4886 0.5056 0.033 Uiso 1 1 calc R . .
C42 C 0.0754(2) 0.49760(12) 0.56757(10) 0.0290(5) Uani 1 1 d . . .
H42 H 0.1275 0.4959 0.6138 0.035 Uiso 1 1 calc R . .
C43 C -0.0814(2) 0.50450(12) 0.56408(10) 0.0273(4) Uani 1 1 d . . .
H43 H -0.1375 0.5077 0.6080 0.033 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C21 1.622(2) . ?
B1 C4 1.681(3) . ?
B1 Cl2 1.8885(19) . ?
B1 Cl3 1.9381(18) . ?
C4 N5 1.352(2) . ?
C4 N12 1.376(2) . ?
N5 C9 1.500(2) . ?
N5 C6 1.508(2) . ?
C6 C8 1.524(3) . ?
C6 C7 1.532(2) . ?
C6 H6 1.0000 . ?
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 C11 1.528(2) . ?
C9 C10 1.538(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N12 C16 1.490(2) . ?
N12 C13 1.503(2) . ?
C13 C15 1.529(3) . ?
C13 C14 1.532(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.526(2) . ?
C16 C17 1.531(2) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C26 1.417(2) . ?
C21 C22 1.419(2) . ?
C22 C23 1.404(2) . ?
C22 C27 1.516(2) . ?
C23 C24 1.386(2) . ?
C23 C28 1.515(2) . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.408(2) . ?
C25 C29 1.512(2) . ?
C26 C30 1.515(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
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 . ?
C41 C43 1.381(3) 3_566 ?
C41 C42 1.386(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(3) . ?
C42 H42 0.9500 . ?
C43 C41 1.381(3) 3_566 ?
C43 H43 0.9500 . ?

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
C21 B1 C4 118.88(13) . . ?
C21 B1 Cl2 108.22(12) . . ?
C4 B1 Cl2 114.91(11) . . ?
C21 B1 Cl3 114.53(11) . . ?
C4 B1 Cl3 95.19(10) . . ?
Cl2 B1 Cl3 103.71(9) . . ?
N5 C4 N12 116.96(15) . . ?
N5 C4 B1 121.36(13) . . ?
N12 C4 B1 120.86(14) . . ?
C4 N5 C9 119.83(14) . . ?
C4 N5 C6 120.67(13) . . ?
C9 N5 C6 119.49(13) . . ?
N5 C6 C8 115.34(14) . . ?
N5 C6 C7 112.84(14) . . ?
C8 C6 C7 110.51(15) . . ?
N5 C6 H6 105.8 . . ?
C8 C6 H6 105.8 . . ?
C7 C6 H6 105.8 . . ?
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 . . ?
N5 C9 C11 114.88(13) . . ?
N5 C9 C10 112.06(13) . . ?
C11 C9 C10 110.80(14) . . ?
N5 C9 H9 106.1 . . ?
C11 C9 H9 106.1 . . ?
C10 C9 H9 106.1 . . ?
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 . . ?
C4 N12 C16 119.20(14) . . ?
C4 N12 C13 118.22(13) . . ?
C16 N12 C13 122.57(13) . . ?
N12 C13 C15 116.68(14) . . ?
N12 C13 C14 110.25(15) . . ?
C15 C13 C14 110.52(14) . . ?
N12 C13 H13 106.2 . . ?
C15 C13 H13 106.2 . . ?
C14 C13 H13 106.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N12 C16 C18 115.52(14) . . ?
N12 C16 C17 110.76(14) . . ?
C18 C16 C17 111.01(14) . . ?
N12 C16 H16 106.3 . . ?
C18 C16 H16 106.3 . . ?
C17 C16 H16 106.3 . . ?
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 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C21 C22 117.58(14) . . ?
C26 C21 B1 119.96(14) . . ?
C22 C21 B1 122.46(14) . . ?
C23 C22 C21 120.50(15) . . ?
C23 C22 C27 116.88(15) . . ?
C21 C22 C27 122.45(15) . . ?
C24 C23 C22 119.31(16) . . ?
C24 C23 C28 119.48(15) . . ?
C22 C23 C28 121.21(15) . . ?
C25 C24 C23 121.75(15) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 118.99(15) . . ?
C24 C25 C29 119.86(15) . . ?
C26 C25 C29 121.15(15) . . ?
C25 C26 C21 120.83(15) . . ?
C25 C26 C30 116.67(14) . . ?
C21 C26 C30 122.39(14) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
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 . . ?
C26 C30 H30A 109.5 . . ?
C26 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C26 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C43 C41 C42 120.32(17) 3_566 . ?
C43 C41 H41 119.8 3_566 . ?
C42 C41 H41 119.8 . . ?
C43 C42 C41 119.76(17) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C42 C43 C41 119.91(18) . 3_566 ?
C42 C43 H43 120.0 . . ?
C41 C43 H43 120.0 3_566 . ?

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
C21 B1 C4 N5 -42.7(2) . . . . ?
Cl2 B1 C4 N5 -173.24(11) . . . . ?
Cl3 B1 C4 N5 79.04(14) . . . . ?
C21 B1 C4 N12 148.00(14) . . . . ?
Cl2 B1 C4 N12 17.47(18) . . . . ?
Cl3 B1 C4 N12 -90.26(14) . . . . ?
N12 C4 N5 C9 154.24(13) . . . . ?
B1 C4 N5 C9 -15.5(2) . . . . ?
N12 C4 N5 C6 -24.5(2) . . . . ?
B1 C4 N5 C6 165.81(14) . . . . ?
C4 N5 C6 C8 127.99(16) . . . . ?
C9 N5 C6 C8 -50.75(19) . . . . ?
C4 N5 C6 C7 -103.69(17) . . . . ?
C9 N5 C6 C7 77.57(18) . . . . ?
C4 N5 C9 C11 130.81(16) . . . . ?
C6 N5 C9 C11 -50.4(2) . . . . ?
C4 N5 C9 C10 -101.58(18) . . . . ?
C6 N5 C9 C10 77.17(18) . . . . ?
N5 C4 N12 C16 128.58(15) . . . . ?
B1 C4 N12 C16 -61.67(19) . . . . ?
N5 C4 N12 C13 -52.25(19) . . . . ?
B1 C4 N12 C13 117.50(16) . . . . ?
C4 N12 C13 C15 135.19(16) . . . . ?
C16 N12 C13 C15 -45.7(2) . . . . ?
C4 N12 C13 C14 -97.69(17) . . . . ?
C16 N12 C13 C14 81.45(19) . . . . ?
C4 N12 C16 C18 136.42(17) . . . . ?
C13 N12 C16 C18 -42.7(2) . . . . ?
C4 N12 C16 C17 -96.29(18) . . . . ?
C13 N12 C16 C17 84.58(19) . . . . ?
C4 B1 C21 C26 -37.9(2) . . . . ?
Cl2 B1 C21 C26 95.60(16) . . . . ?
Cl3 B1 C21 C26 -149.28(13) . . . . ?
C4 B1 C21 C22 141.04(15) . . . . ?
Cl2 B1 C21 C22 -85.50(16) . . . . ?
Cl3 B1 C21 C22 29.6(2) . . . . ?
C26 C21 C22 C23 11.1(2) . . . . ?
B1 C21 C22 C23 -167.84(16) . . . . ?
C26 C21 C22 C27 -164.17(16) . . . . ?
B1 C21 C22 C27 16.9(2) . . . . ?
C21 C22 C23 C24 -4.4(3) . . . . ?
C27 C22 C23 C24 171.14(16) . . . . ?
C21 C22 C23 C28 175.45(15) . . . . ?
C27 C22 C23 C28 -9.0(2) . . . . ?
C22 C23 C24 C25 -4.2(3) . . . . ?
C28 C23 C24 C25 176.00(16) . . . . ?
C23 C24 C25 C26 5.5(3) . . . . ?
C23 C24 C25 C29 -175.11(17) . . . . ?
C24 C25 C26 C21 1.7(3) . . . . ?
C29 C25 C26 C21 -177.70(16) . . . . ?
C24 C25 C26 C30 -174.62(16) . . . . ?
C29 C25 C26 C30 6.0(2) . . . . ?
C22 C21 C26 C25 -9.7(2) . . . . ?
B1 C21 C26 C25 169.22(15) . . . . ?
C22 C21 C26 C30 166.33(15) . . . . ?
B1 C21 C26 C30 -14.7(2) . . . . ?
C43 C41 C42 C43 -0.2(3) 3_566 . . . ?
C41 C42 C43 C41 0.2(3) . . . 3_566 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.056
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FlHu169
_database_code_depnum_ccdc_archive 'CCDC 1042592'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
?
;
_chemical_name_common            
;
?
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H39 B Cl2 N2'

_chemical_formula_sum            'C22 H39 B Cl2 N2'
_chemical_formula_weight         413.26

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.4091(17)
_cell_length_b                   23.915(5)
_cell_length_c                   13.429(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.008(7)
_cell_angle_gamma                90.00
_cell_volume                     2700.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.017
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6195
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Sadabs 2008/1 (Bruker 2008)'

_exptl_special_details           
; 
 The crystal was immersed in a film of perfluoropolyether oil, mounted
on a a glass fiber and transferred to stream of cold nitrogen. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5521
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0689
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5521
_reflns_number_gt                3912
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 ver. 2010.3 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5521
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.2453
_refine_ls_wR_factor_gt          0.2268
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17911(9) 0.23524(3) 0.26720(6) 0.0257(3) Uani 1 1 d . . .
N1 N 0.1328(3) 0.27383(11) 0.51078(19) 0.0225(6) Uani 1 1 d . . .
C1 C 0.1248(3) 0.21798(15) 0.4905(2) 0.0236(7) Uani 1 1 d . . .
B1 B 0.1104(4) 0.19043(16) 0.3760(3) 0.0239(8) Uani 1 1 d . . .
Cl2 Cl -0.11662(9) 0.19437(4) 0.35941(6) 0.0296(3) Uani 1 1 d . . .
N2 N 0.1069(3) 0.18311(11) 0.57003(19) 0.0232(6) Uani 1 1 d . . .
C11 C 0.2006(4) 0.13077(14) 0.3657(2) 0.0249(7) Uani 1 1 d . . .
C12 C 0.1336(4) 0.08010(15) 0.3300(2) 0.0287(8) Uani 1 1 d . . .
C13 C 0.2247(4) 0.03118(15) 0.3254(2) 0.0297(8) Uani 1 1 d . . .
H13 H 0.1755 -0.0022 0.3018 0.036 Uiso 1 1 calc R . .
C14 C 0.3832(4) 0.02946(15) 0.3538(2) 0.0295(8) Uani 1 1 d . . .
C15 C 0.4515(4) 0.07980(15) 0.3849(2) 0.0277(8) Uani 1 1 d . . .
H15 H 0.5614 0.0803 0.4023 0.033 Uiso 1 1 calc R . .
C16 C 0.3654(4) 0.12923(14) 0.3913(2) 0.0240(7) Uani 1 1 d . . .
C17 C -0.0386(5) 0.07300(17) 0.2935(3) 0.0435(10) Uani 1 1 d . . .
H17A H -0.1095 0.0736 0.3506 0.065 Uiso 1 1 calc R . .
H17B H -0.0498 0.0372 0.2584 0.065 Uiso 1 1 calc R . .
H17C H -0.0667 0.1036 0.2480 0.065 Uiso 1 1 calc R . .
C18 C 0.4805(5) -0.02363(16) 0.3487(3) 0.0417(10) Uani 1 1 d . . .
H18A H 0.4341 -0.0486 0.2980 0.063 Uiso 1 1 calc R . .
H18B H 0.4803 -0.0423 0.4136 0.063 Uiso 1 1 calc R . .
H18C H 0.5900 -0.0144 0.3311 0.063 Uiso 1 1 calc R . .
C19 C 0.4584(4) 0.18084(16) 0.4207(2) 0.0285(8) Uani 1 1 d . . .
H19A H 0.4617 0.2067 0.3641 0.043 Uiso 1 1 calc R . .
H19B H 0.5671 0.1702 0.4403 0.043 Uiso 1 1 calc R . .
H19C H 0.4069 0.1992 0.4769 0.043 Uiso 1 1 calc R . .
C21 C 0.2521(4) 0.30925(15) 0.4592(3) 0.0283(8) Uani 1 1 d . . .
H21 H 0.2968 0.2852 0.4056 0.034 Uiso 1 1 calc R . .
C22 C 0.3933(4) 0.32363(18) 0.5293(3) 0.0367(9) Uani 1 1 d . . .
H22A H 0.4194 0.2911 0.5709 0.055 Uiso 1 1 calc R . .
H22B H 0.3646 0.3552 0.5719 0.055 Uiso 1 1 calc R . .
H22C H 0.4857 0.3337 0.4896 0.055 Uiso 1 1 calc R . .
C23 C 0.1844(4) 0.36058(15) 0.4068(3) 0.0325(8) Uani 1 1 d . . .
H23A H 0.1428 0.3866 0.4563 0.049 Uiso 1 1 calc R . .
H23B H 0.0984 0.3492 0.3610 0.049 Uiso 1 1 calc R . .
H23C H 0.2685 0.3790 0.3692 0.049 Uiso 1 1 calc R . .
C24 C 0.0155(4) 0.29908(14) 0.5815(2) 0.0265(8) Uani 1 1 d . . .
H24 H -0.0257 0.2675 0.6224 0.032 Uiso 1 1 calc R . .
C25 C -0.1287(4) 0.32243(17) 0.5227(3) 0.0346(8) Uani 1 1 d . . .
H25A H -0.1624 0.2954 0.4717 0.052 Uiso 1 1 calc R . .
H25B H -0.0992 0.3577 0.4906 0.052 Uiso 1 1 calc R . .
H25C H -0.2164 0.3291 0.5683 0.052 Uiso 1 1 calc R . .
C26 C 0.0789(4) 0.34170(15) 0.6541(3) 0.0329(8) Uani 1 1 d . . .
H26A H 0.1227 0.3735 0.6175 0.049 Uiso 1 1 calc R . .
H26B H 0.1628 0.3248 0.6956 0.049 Uiso 1 1 calc R . .
H26C H -0.0073 0.3547 0.6964 0.049 Uiso 1 1 calc R . .
C31 C 0.1858(4) 0.19778(14) 0.6686(2) 0.0233(7) Uani 1 1 d . . .
H31 H 0.2151 0.2383 0.6653 0.028 Uiso 1 1 calc R . .
C32 C 0.0806(4) 0.19074(15) 0.7588(2) 0.0292(8) Uani 1 1 d . . .
H32A H 0.0542 0.1511 0.7671 0.044 Uiso 1 1 calc R . .
H32B H -0.0175 0.2123 0.7489 0.044 Uiso 1 1 calc R . .
H32C H 0.1372 0.2043 0.8185 0.044 Uiso 1 1 calc R . .
C33 C 0.3412(4) 0.16504(14) 0.6843(3) 0.0272(7) Uani 1 1 d . . .
H33A H 0.3951 0.1612 0.6206 0.041 Uiso 1 1 calc R . .
H33B H 0.3173 0.1279 0.7109 0.041 Uiso 1 1 calc R . .
H33C H 0.4105 0.1852 0.7316 0.041 Uiso 1 1 calc R . .
C34 C 0.0148(4) 0.12998(15) 0.5576(3) 0.0284(8) Uani 1 1 d . . .
H34 H 0.0001 0.1249 0.4841 0.034 Uiso 1 1 calc R . .
C35 C -0.1534(4) 0.13599(17) 0.5987(3) 0.0342(9) Uani 1 1 d . . .
H35A H -0.1990 0.1718 0.5771 0.051 Uiso 1 1 calc R . .
H35B H -0.1485 0.1347 0.6717 0.051 Uiso 1 1 calc R . .
H35C H -0.2202 0.1053 0.5737 0.051 Uiso 1 1 calc R . .
C36 C 0.1000(4) 0.07712(15) 0.5942(3) 0.0305(8) Uani 1 1 d . . .
H36A H 0.1109 0.0782 0.6670 0.046 Uiso 1 1 calc R . .
H36B H 0.2058 0.0751 0.5649 0.046 Uiso 1 1 calc R . .
H36C H 0.0381 0.0441 0.5743 0.046 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.910(4) . ?
N1 C1 1.364(5) . ?
N1 C21 1.493(4) . ?
N1 C24 1.508(4) . ?
C1 N2 1.365(4) . ?
C1 B1 1.676(5) . ?
B1 C11 1.623(5) . ?
B1 Cl2 1.920(4) . ?
N2 C34 1.496(4) . ?
N2 C31 1.512(4) . ?
C11 C12 1.416(5) . ?
C11 C16 1.423(4) . ?
C12 C13 1.400(5) . ?
C12 C17 1.530(5) . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(5) . ?
C14 C18 1.513(5) . ?
C15 C16 1.389(5) . ?
C15 H15 0.9500 . ?
C16 C19 1.510(5) . ?
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 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C23 1.521(5) . ?
C21 C22 1.541(5) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C26 1.502(5) . ?
C24 C25 1.540(4) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C31 C33 1.535(4) . ?
C31 C32 1.522(5) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C36 1.530(5) . ?
C34 C35 1.534(5) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C1 N1 C21 119.6(3) . . ?
C1 N1 C24 119.1(3) . . ?
C21 N1 C24 121.2(3) . . ?
N1 C1 N2 116.6(3) . . ?
N1 C1 B1 124.8(3) . . ?
N2 C1 B1 118.1(3) . . ?
C11 B1 C1 113.5(3) . . ?
C11 B1 Cl2 119.9(2) . . ?
C1 B1 Cl2 98.2(2) . . ?
C11 B1 Cl1 106.3(2) . . ?
C1 B1 Cl1 117.6(2) . . ?
Cl2 B1 Cl1 101.37(16) . . ?
C1 N2 C34 119.7(3) . . ?
C1 N2 C31 119.3(3) . . ?
C34 N2 C31 120.9(3) . . ?
C12 C11 C16 116.1(3) . . ?
C12 C11 B1 126.7(3) . . ?
C16 C11 B1 117.2(3) . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 C17 124.9(3) . . ?
C13 C12 C17 114.1(3) . . ?
C14 C13 C12 122.6(3) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 116.6(3) . . ?
C13 C14 C18 122.2(3) . . ?
C15 C14 C18 121.2(3) . . ?
C16 C15 C14 122.7(3) . . ?
C16 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 C19 116.3(3) . . ?
C11 C16 C19 122.7(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C21 C23 115.1(3) . . ?
N1 C21 C22 111.1(3) . . ?
C23 C21 C22 112.4(3) . . ?
N1 C21 H21 105.8 . . ?
C23 C21 H21 105.8 . . ?
C22 C21 H21 105.8 . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 C26 116.8(3) . . ?
N1 C24 C25 109.9(3) . . ?
C26 C24 C25 110.8(3) . . ?
N1 C24 H24 106.2 . . ?
C26 C24 H24 106.2 . . ?
C25 C24 H24 106.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C31 C33 111.2(3) . . ?
N2 C31 C32 114.7(3) . . ?
C33 C31 C32 109.9(3) . . ?
N2 C31 H31 106.9 . . ?
C33 C31 H31 106.9 . . ?
C32 C31 H31 106.9 . . ?
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 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N2 C34 C36 115.3(3) . . ?
N2 C34 C35 111.0(3) . . ?
C36 C34 C35 113.0(3) . . ?
N2 C34 H34 105.5 . . ?
C36 C34 H34 105.5 . . ?
C35 C34 H34 105.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
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 . . ?

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
C21 N1 C1 N2 137.5(3) . . . . ?
C24 N1 C1 N2 -45.4(4) . . . . ?
C21 N1 C1 B1 -51.3(4) . . . . ?
C24 N1 C1 B1 125.8(3) . . . . ?
N1 C1 B1 C11 146.6(3) . . . . ?
N2 C1 B1 C11 -42.3(4) . . . . ?
N1 C1 B1 Cl2 -85.7(3) . . . . ?
N2 C1 B1 Cl2 85.4(3) . . . . ?
N1 C1 B1 Cl1 21.8(4) . . . . ?
N2 C1 B1 Cl1 -167.1(2) . . . . ?
N1 C1 N2 C34 147.6(3) . . . . ?
B1 C1 N2 C34 -24.3(4) . . . . ?
N1 C1 N2 C31 -34.7(4) . . . . ?
B1 C1 N2 C31 153.4(3) . . . . ?
C1 B1 C11 C12 125.9(3) . . . . ?
Cl2 B1 C11 C12 10.5(4) . . . . ?
Cl1 B1 C11 C12 -103.4(3) . . . . ?
C1 B1 C11 C16 -56.7(4) . . . . ?
Cl2 B1 C11 C16 -172.1(2) . . . . ?
Cl1 B1 C11 C16 74.1(3) . . . . ?
C16 C11 C12 C13 3.0(5) . . . . ?
B1 C11 C12 C13 -179.6(3) . . . . ?
C16 C11 C12 C17 -176.8(3) . . . . ?
B1 C11 C12 C17 0.6(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C17 C12 C13 C14 179.1(3) . . . . ?
C12 C13 C14 C15 -2.0(5) . . . . ?
C12 C13 C14 C18 179.9(3) . . . . ?
C13 C14 C15 C16 2.5(5) . . . . ?
C18 C14 C15 C16 -179.4(3) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
C14 C15 C16 C19 -176.7(3) . . . . ?
C12 C11 C16 C15 -2.5(4) . . . . ?
B1 C11 C16 C15 179.8(3) . . . . ?
C12 C11 C16 C19 173.8(3) . . . . ?
B1 C11 C16 C19 -3.9(4) . . . . ?
C1 N1 C21 C23 126.8(3) . . . . ?
C24 N1 C21 C23 -50.3(4) . . . . ?
C1 N1 C21 C22 -104.0(3) . . . . ?
C24 N1 C21 C22 78.9(4) . . . . ?
C1 N1 C24 C26 139.1(3) . . . . ?
C21 N1 C24 C26 -43.7(4) . . . . ?
C1 N1 C24 C25 -93.6(3) . . . . ?
C21 N1 C24 C25 83.5(4) . . . . ?
C1 N2 C31 C33 -99.7(3) . . . . ?
C34 N2 C31 C33 78.0(4) . . . . ?
C1 N2 C31 C32 134.9(3) . . . . ?
C34 N2 C31 C32 -47.4(4) . . . . ?
C1 N2 C34 C36 128.3(3) . . . . ?
C31 N2 C34 C36 -49.4(4) . . . . ?
C1 N2 C34 C35 -101.5(3) . . . . ?
C31 N2 C34 C35 80.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.067


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 -0.012 0.000 0.000 241 64 ' '
2 -0.025 0.500 0.500 241 64 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FlHu160
_database_code_depnum_ccdc_archive 'CCDC 1042593'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
?
;
_chemical_name_common            
;
?
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H28 B Br2 N2'

_chemical_formula_sum            'C13 H28 B Br2 N2'
_chemical_formula_weight         383.00

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'
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   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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                   7.1189(6)
_cell_length_b                   15.9168(14)
_cell_length_c                   15.0043(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.677(3)
_cell_angle_gamma                90.00
_cell_volume                     1699.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9838
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      27.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    4.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5241
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'Sadabs 2008/1 (Bruker 2008)'

_exptl_special_details           
; 
 The crystal was immersed in a film of perfluoropolyether oil, mounted
on a a glass fiber and transferred to stream of cold nitrogen. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'ImS micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32098
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3473
_reflns_number_gt                3264
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 ver. 2012.4-3 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. 8.18C (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 8.18C (Bruker AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0290P)²+1.2050P] 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         3473
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0578
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.38240(3) 0.309696(12) 0.611022(11) 0.01745(7) Uani 1 1 d . . .
B1 B 0.4509(3) 0.20648(13) 0.53707(13) 0.0134(4) Uani 1 1 d . . .
Br2 Br 0.68612(3) 0.146756(12) 0.590482(12) 0.01896(7) Uani 1 1 d . . .
C2 C 0.2829(3) 0.14094(12) 0.52194(12) 0.0153(4) Uani 1 1 d . . .
H2A H 0.2846 0.0978 0.5695 0.018 Uiso 1 1 calc R . .
H2B H 0.1598 0.1699 0.5210 0.018 Uiso 1 1 calc R . .
C3 C 0.3204(2) 0.10123(12) 0.43114(12) 0.0133(3) Uani 1 1 d . . .
H3 H 0.4056 0.0519 0.4403 0.016 Uiso 1 1 calc R . .
N4 N 0.4235(2) 0.16824(10) 0.38124(9) 0.0113(3) Uani 1 1 d . . .
C5 C 0.4909(2) 0.22985(11) 0.43400(11) 0.0111(3) Uani 1 1 d . . .
H5 H 0.6163 0.2016 0.4385 0.013 Uiso 1 1 calc R . .
N6 N 0.5706(2) 0.30021(9) 0.40169(10) 0.0116(3) Uani 1 1 d . . .
C10 C 0.1418(3) 0.07214(13) 0.38128(13) 0.0183(4) Uani 1 1 d . . .
H10A H 0.0687 0.1212 0.3615 0.028 Uiso 1 1 calc R . .
H10B H 0.0664 0.0379 0.4211 0.028 Uiso 1 1 calc R . .
H10C H 0.1756 0.0386 0.3294 0.028 Uiso 1 1 calc R . .
C11 C 0.4923(3) 0.34111(12) 0.31894(11) 0.0133(4) Uani 1 1 d . . .
H11 H 0.4068 0.2988 0.2897 0.016 Uiso 1 1 calc R . .
C12 C 0.3686(3) 0.41674(12) 0.34155(12) 0.0174(4) Uani 1 1 d . . .
H12A H 0.2991 0.4045 0.3955 0.026 Uiso 1 1 calc R . .
H12B H 0.2796 0.4277 0.2918 0.026 Uiso 1 1 calc R . .
H12C H 0.4480 0.4663 0.3518 0.026 Uiso 1 1 calc R . .
C13 C 0.6376(3) 0.36424(13) 0.24978(12) 0.0190(4) Uani 1 1 d . . .
H13A H 0.7227 0.4072 0.2746 0.028 Uiso 1 1 calc R . .
H13B H 0.5731 0.3862 0.1961 0.028 Uiso 1 1 calc R . .
H13C H 0.7099 0.3142 0.2344 0.028 Uiso 1 1 calc R . .
C21 C 0.7290(2) 0.33641(12) 0.45681(12) 0.0144(4) Uani 1 1 d . . .
H21 H 0.7183 0.3120 0.5178 0.017 Uiso 1 1 calc R . .
C22 C 0.7279(3) 0.43140(12) 0.46854(13) 0.0193(4) Uani 1 1 d . . .
H22A H 0.7429 0.4585 0.4105 0.029 Uiso 1 1 calc R . .
H22B H 0.8317 0.4480 0.5091 0.029 Uiso 1 1 calc R . .
H22C H 0.6083 0.4488 0.4935 0.029 Uiso 1 1 calc R . .
C23 C 0.9168(3) 0.30519(14) 0.42158(15) 0.0235(4) Uani 1 1 d . . .
H23A H 0.9132 0.2439 0.4156 0.035 Uiso 1 1 calc R . .
H23B H 1.0190 0.3212 0.4634 0.035 Uiso 1 1 calc R . .
H23C H 0.9381 0.3306 0.3632 0.035 Uiso 1 1 calc R . .
C31 C 0.5058(3) 0.14858(11) 0.29270(12) 0.0136(4) Uani 1 1 d . . .
H31 H 0.6019 0.1929 0.2815 0.016 Uiso 1 1 calc R . .
C32 C 0.6104(3) 0.06465(12) 0.29753(13) 0.0192(4) Uani 1 1 d . . .
H32A H 0.6925 0.0634 0.3511 0.029 Uiso 1 1 calc R . .
H32B H 0.6864 0.0581 0.2446 0.029 Uiso 1 1 calc R . .
H32C H 0.5194 0.0186 0.3000 0.029 Uiso 1 1 calc R . .
C33 C 0.3647(3) 0.15076(13) 0.21338(12) 0.0206(4) Uani 1 1 d . . .
H33A H 0.2915 0.0986 0.2119 0.031 Uiso 1 1 calc R . .
H33B H 0.4326 0.1563 0.1578 0.031 Uiso 1 1 calc R . .
H33C H 0.2798 0.1987 0.2198 0.031 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 2.049(2) . ?
B1 C2 1.598(3) . ?
B1 C5 1.624(2) . ?
B1 Br2 2.067(2) . ?
C2 C3 1.532(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.507(2) . ?
C3 C10 1.528(2) . ?
C3 H3 1.0000 . ?
N4 C5 1.340(2) . ?
N4 C31 1.501(2) . ?
C5 N6 1.352(2) . ?
C5 H5 1.0000 . ?
N6 C21 1.495(2) . ?
N6 C11 1.495(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.531(2) . ?
C11 C12 1.535(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 C22 1.522(3) . ?
C21 C23 1.534(3) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C31 C32 1.530(3) . ?
C31 C33 1.535(3) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C2 B1 C5 99.53(14) . . ?
C2 B1 Br1 114.29(13) . . ?
C5 B1 Br1 112.53(13) . . ?
C2 B1 Br2 110.44(13) . . ?
C5 B1 Br2 108.18(12) . . ?
Br1 B1 Br2 111.20(9) . . ?
C3 C2 B1 104.28(14) . . ?
C3 C2 H2A 110.9 . . ?
B1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
B1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N4 C3 C10 112.46(14) . . ?
N4 C3 C2 104.47(14) . . ?
C10 C3 C2 113.35(15) . . ?
N4 C3 H3 108.8 . . ?
C10 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C5 N4 C31 122.22(15) . . ?
C5 N4 C3 113.31(14) . . ?
C31 N4 C3 120.06(14) . . ?
N4 C5 N6 122.76(15) . . ?
N4 C5 B1 108.98(15) . . ?
N6 C5 B1 128.20(16) . . ?
N4 C5 H5 90.8 . . ?
N6 C5 H5 90.8 . . ?
B1 C5 H5 90.8 . . ?
C5 N6 C21 116.03(14) . . ?
C5 N6 C11 120.55(14) . . ?
C21 N6 C11 123.28(15) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 C13 115.12(15) . . ?
N6 C11 C12 111.11(14) . . ?
C13 C11 C12 111.37(15) . . ?
N6 C11 H11 106.2 . . ?
C13 C11 H11 106.2 . . ?
C12 C11 H11 106.2 . . ?
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 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N6 C21 C22 116.13(15) . . ?
N6 C21 C23 109.59(15) . . ?
C22 C21 C23 111.67(16) . . ?
N6 C21 H21 106.3 . . ?
C22 C21 H21 106.3 . . ?
C23 C21 H21 106.3 . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C31 C32 110.02(14) . . ?
N4 C31 C33 114.69(15) . . ?
C32 C31 C33 111.29(15) . . ?
N4 C31 H31 106.8 . . ?
C32 C31 H31 106.8 . . ?
C33 C31 H31 106.8 . . ?
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 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C5 B1 C2 C3 29.34(17) . . . . ?
Br1 B1 C2 C3 149.48(12) . . . . ?
Br2 B1 C2 C3 -84.25(15) . . . . ?
B1 C2 C3 N4 -28.22(17) . . . . ?
B1 C2 C3 C10 -150.98(16) . . . . ?
C10 C3 N4 C5 138.74(16) . . . . ?
C2 C3 N4 C5 15.41(19) . . . . ?
C10 C3 N4 C31 -64.3(2) . . . . ?
C2 C3 N4 C31 172.37(14) . . . . ?
C31 N4 C5 N6 30.6(2) . . . . ?
C3 N4 C5 N6 -172.96(15) . . . . ?
C31 N4 C5 B1 -151.92(15) . . . . ?
C3 N4 C5 B1 4.48(19) . . . . ?
C2 B1 C5 N4 -21.31(18) . . . . ?
Br1 B1 C5 N4 -142.72(13) . . . . ?
Br2 B1 C5 N4 94.02(14) . . . . ?
C2 B1 C5 N6 155.95(17) . . . . ?
Br1 B1 C5 N6 34.5(2) . . . . ?
Br2 B1 C5 N6 -88.72(19) . . . . ?
N4 C5 N6 C21 -145.50(16) . . . . ?
B1 C5 N6 C21 37.6(2) . . . . ?
N4 C5 N6 C11 38.7(2) . . . . ?
B1 C5 N6 C11 -138.22(18) . . . . ?
C5 N6 C11 C13 -132.36(17) . . . . ?
C21 N6 C11 C13 52.2(2) . . . . ?
C5 N6 C11 C12 99.87(18) . . . . ?
C21 N6 C11 C12 -75.6(2) . . . . ?
C5 N6 C21 C22 -136.43(17) . . . . ?
C11 N6 C21 C22 39.3(2) . . . . ?
C5 N6 C21 C23 95.90(18) . . . . ?
C11 N6 C21 C23 -88.4(2) . . . . ?
C5 N4 C31 C32 109.33(18) . . . . ?
C3 N4 C31 C32 -45.5(2) . . . . ?
C5 N4 C31 C33 -124.32(18) . . . . ?
C3 N4 C31 C33 80.81(19) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.599
_refine_diff_density_min         -1.113
_refine_diff_density_rms         0.072
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AD300
_database_code_depnum_ccdc_archive 'CCDC 1042594'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H41 B N2'
_chemical_formula_sum            'C23 H41 B N2'
_chemical_formula_weight         356.39

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

_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                   8.8938(17)
_cell_length_b                   9.258(2)
_cell_length_c                   15.064(3)
_cell_angle_alpha                73.468(12)
_cell_angle_beta                 79.717(9)
_cell_angle_gamma                77.485(8)
_cell_volume                     1151.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4498
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6326
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SadAbs 2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            22668
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.421
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4534
_reflns_number_gt                3277
_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       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.27B (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.27B (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 One of iso-propyl group was showing rotational disorder. The coordinates and 
 displacement parameters of methine atoms of this group were constrained to 
 the same value (EXYZ and EADP keywords). The main four-membered ring was 
 disordered (86:14). The geometry of disordered parts were restrained with SAME 
 keyword. The displacement parameters of atoms belonging to disordered residues 
 were constrained to the same value with similarity restraint SIMU and with 
 'enhnaced rigid bond' restraint RIGU.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.4943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4534
_refine_ls_number_parameters     377
_refine_ls_number_restraints     498
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.006
_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
N1_1 N 0.65928(16) 0.39742(15) 0.24041(10) 0.0219(3) Uani 1 1 d D . . . .
B2_1 B 0.4980(2) 0.4099(2) 0.25667(14) 0.0225(4) Uani 1 1 d . . . . .
C3_1 C 0.35862(19) 0.54811(17) 0.25548(12) 0.0213(4) Uani 1 1 d . . . . .
C4_1 C 0.3038(2) 0.63888(18) 0.17167(12) 0.0235(4) Uani 1 1 d . . . . .
C5_1 C 0.1719(2) 0.75444(18) 0.17316(13) 0.0255(4) Uani 1 1 d . . . . .
C6_1 C 0.0988(2) 0.77691(19) 0.25868(13) 0.0277(4) Uani 1 1 d . . . . .
H6_1 H 0.0100 0.8551 0.2597 0.033 Uiso 1 1 calc R U . . .
C7_1 C 0.1495(2) 0.69037(19) 0.34294(13) 0.0257(4) Uani 1 1 d . . . . .
C8_1 C 0.2812(2) 0.57515(18) 0.34146(12) 0.0218(4) Uani 1 1 d . . . . .
C9_1 C 0.3834(2) 0.6134(2) 0.07885(12) 0.0311(5) Uani 1 1 d . . . . .
H9A_1 H 0.4121 0.7094 0.0384 0.047 Uiso 1 1 calc R U . . .
H9B_1 H 0.3128 0.5790 0.0493 0.047 Uiso 1 1 calc R U . . .
H9C_1 H 0.4771 0.5353 0.0885 0.047 Uiso 1 1 calc R U . . .
C10_1 C 0.1109(2) 0.8520(2) 0.08386(14) 0.0346(5) Uani 1 1 d . . . . .
H10A_1 H 0.0172 0.9235 0.0986 0.052 Uiso 1 1 calc R U . . .
H10B_1 H 0.0858 0.7862 0.0499 0.052 Uiso 1 1 calc R U . . .
H10C_1 H 0.1901 0.9096 0.0451 0.052 Uiso 1 1 calc R U . . .
C11_1 C 0.0636(2) 0.7198(2) 0.43379(14) 0.0341(5) Uani 1 1 d . . . . .
H11A_1 H 0.0347 0.6244 0.4750 0.051 Uiso 1 1 calc R U . . .
H11B_1 H -0.0304 0.7965 0.4214 0.051 Uiso 1 1 calc R U . . .
H11C_1 H 0.1305 0.7576 0.4639 0.051 Uiso 1 1 calc R U . . .
C12_1 C 0.3397(2) 0.4814(2) 0.43266(12) 0.0287(4) Uani 1 1 d . . . . .
H12A_1 H 0.3486 0.5501 0.4697 0.043 Uiso 1 1 calc R U . . .
H12B_1 H 0.4417 0.4200 0.4198 0.043 Uiso 1 1 calc R U . . .
H12C_1 H 0.2666 0.4135 0.4675 0.043 Uiso 1 1 calc R U . . .
C1_2 C 0.7778(4) 0.4938(4) 0.2165(2) 0.0329(5) Uani 0.606(5) 1 d D U P A 1
H1_2 H 0.8699 0.4338 0.2482 0.039 Uiso 0.606(5) 1 calc R U P A 1
C2_2 C 0.7180(5) 0.6327(5) 0.2548(4) 0.070(2) Uani 0.606(5) 1 d D U P A 1
H2A_2 H 0.7992 0.6951 0.2415 0.105 Uiso 0.606(5) 1 calc R U P A 1
H2B_2 H 0.6891 0.5996 0.3224 0.105 Uiso 0.606(5) 1 calc R U P A 1
H2C_2 H 0.6268 0.6933 0.2252 0.105 Uiso 0.606(5) 1 calc R U P A 1
C3_2 C 0.8304(5) 0.5370(5) 0.1127(2) 0.0568(14) Uani 0.606(5) 1 d D U P A 1
H3A_2 H 0.9112 0.5999 0.0999 0.085 Uiso 0.606(5) 1 calc R U P A 1
H3B_2 H 0.7419 0.5951 0.0796 0.085 Uiso 0.606(5) 1 calc R U P A 1
H3C_2 H 0.8722 0.4439 0.0913 0.085 Uiso 0.606(5) 1 calc R U P A 1
C1_12 C 0.7734(6) 0.4962(6) 0.2262(3) 0.0329(5) Uani 0.394(5) 1 d D U P A 2
H1_12 H 0.8739 0.4441 0.1985 0.039 Uiso 0.394(5) 1 calc R U P A 2
C2_12 C 0.8007(9) 0.5206(9) 0.3166(4) 0.065(2) Uani 0.394(5) 1 d D U P A 2
H2A_12 H 0.8818 0.5831 0.3040 0.097 Uiso 0.394(5) 1 calc R U P A 2
H2B_12 H 0.8337 0.4214 0.3595 0.097 Uiso 0.394(5) 1 calc R U P A 2
H2C_12 H 0.7044 0.5733 0.3449 0.097 Uiso 0.394(5) 1 calc R U P A 2
C3_12 C 0.7279(10) 0.6480(8) 0.1575(7) 0.082(3) Uani 0.394(5) 1 d D U P A 2
H3A_12 H 0.8074 0.7112 0.1485 0.123 Uiso 0.394(5) 1 calc R U P A 2
H3B_12 H 0.6280 0.7008 0.1818 0.123 Uiso 0.394(5) 1 calc R U P A 2
H3C_12 H 0.7189 0.6305 0.0976 0.123 Uiso 0.394(5) 1 calc R U P A 2
C1_3 C 0.6934(2) 0.2251(2) 0.26431(15) 0.0204(4) Uani 0.8602(16) 1 d D U P A 1
C2_3 C 0.5136(2) 0.2249(2) 0.29392(13) 0.0199(4) Uani 0.8602(16) 1 d D U P A 1
H2_3 H 0.4940 0.1984 0.3636 0.024 Uiso 0.8602(16) 1 calc R U P A 1
N3_3 N 0.4424(2) 0.1251(2) 0.26189(11) 0.0227(4) Uani 0.8602(16) 1 d D U P A 1
C4_3 C 0.7628(2) 0.1602(2) 0.18090(15) 0.0260(5) Uani 0.8602(16) 1 d D U P A 1
H4A_3 H 0.7559 0.0514 0.1969 0.039 Uiso 0.8602(16) 1 calc R U P A 1
H4B_3 H 0.8719 0.1721 0.1642 0.039 Uiso 0.8602(16) 1 calc R U P A 1
H4C_3 H 0.7053 0.2154 0.1279 0.039 Uiso 0.8602(16) 1 calc R U P A 1
C5_3 C 0.7909(3) 0.1538(3) 0.34436(17) 0.0295(5) Uani 0.8602(16) 1 d D U P A 1
H5A_3 H 0.7886 0.0439 0.3662 0.044 Uiso 0.8602(16) 1 calc R U P A 1
H5B_3 H 0.7488 0.2022 0.3957 0.044 Uiso 0.8602(16) 1 calc R U P A 1
H5C_3 H 0.8983 0.1694 0.3228 0.044 Uiso 0.8602(16) 1 calc R U P A 1
C1_4 C 0.3815(3) 0.1885(2) 0.17167(14) 0.0266(4) Uani 0.8602(16) 1 d D U P A 1
H1_4 H 0.4426 0.2697 0.1349 0.032 Uiso 0.8602(16) 1 calc R U P A 1
C2_4 C 0.2091(3) 0.2656(3) 0.17575(17) 0.0353(6) Uani 0.8602(16) 1 d D U P A 1
H2A_4 H 0.1826 0.3126 0.1122 0.053 Uiso 0.8602(16) 1 calc R U P A 1
H2B_4 H 0.1912 0.3446 0.2100 0.053 Uiso 0.8602(16) 1 calc R U P A 1
H2C_4 H 0.1439 0.1886 0.2077 0.053 Uiso 0.8602(16) 1 calc R U P A 1
C3_4 C 0.4130(3) 0.0663(3) 0.11710(16) 0.0363(6) Uani 0.8602(16) 1 d D U P A 1
H3A_4 H 0.3797 0.1123 0.0551 0.054 Uiso 0.8602(16) 1 calc R U P A 1
H3B_4 H 0.3553 -0.0162 0.1507 0.054 Uiso 0.8602(16) 1 calc R U P A 1
H3C_4 H 0.5244 0.0246 0.1106 0.054 Uiso 0.8602(16) 1 calc R U P A 1
C1_5 C 0.3529(2) 0.0221(2) 0.33454(14) 0.0254(5) Uani 0.8602(16) 1 d D U P A 1
H1_5 H 0.2956 -0.0252 0.3020 0.030 Uiso 0.8602(16) 1 calc R U P A 1
C2_5 C 0.2314(3) 0.0998(3) 0.40111(17) 0.0279(5) Uani 0.8602(16) 1 d D U P A 1
H2A_5 H 0.1644 0.0275 0.4387 0.042 Uiso 0.8602(16) 1 calc R U P A 1
H2B_5 H 0.1682 0.1899 0.3646 0.042 Uiso 0.8602(16) 1 calc R U P A 1
H2C_5 H 0.2844 0.1313 0.4424 0.042 Uiso 0.8602(16) 1 calc R U P A 1
C3_5 C 0.4641(4) -0.1076(3) 0.39018(19) 0.0331(7) Uani 0.8602(16) 1 d D U P A 1
H3A_5 H 0.4045 -0.1779 0.4373 0.050 Uiso 0.8602(16) 1 calc R U P A 1
H3B_5 H 0.5256 -0.0650 0.4211 0.050 Uiso 0.8602(16) 1 calc R U P A 1
H3C_5 H 0.5335 -0.1632 0.3479 0.050 Uiso 0.8602(16) 1 calc R U P A 1
C1_13 C 0.7094(8) 0.2477(10) 0.2217(6) 0.0227(10) Uani 0.1398(16) 1 d D U P A 2
C2_13 C 0.5334(8) 0.2527(9) 0.2144(6) 0.0221(9) Uani 0.1398(16) 1 d D U P A 2
H2_13 H 0.5184 0.2872 0.1469 0.027 Uiso 0.1398(16) 1 calc R U P A 2
N3_13 N 0.4657(10) 0.1168(10) 0.2559(4) 0.0236(8) Uani 0.1398(16) 1 d D U P A 2
C4_13 C 0.8205(11) 0.2390(14) 0.1334(6) 0.029(2) Uani 0.1398(16) 1 d D U P A 2
H4A_13 H 0.8440 0.1335 0.1275 0.044 Uiso 0.1398(16) 1 calc R U P A 2
H4B_13 H 0.9168 0.2715 0.1367 0.044 Uiso 0.1398(16) 1 calc R U P A 2
H4C_13 H 0.7725 0.3065 0.0791 0.044 Uiso 0.1398(16) 1 calc R U P A 2
C5_13 C 0.7712(12) 0.1306(14) 0.3063(7) 0.0251(18) Uani 0.1398(16) 1 d D U P A
2
H5A_13 H 0.7552 0.0289 0.3068 0.038 Uiso 0.1398(16) 1 calc R U P A 2
H5B_13 H 0.7161 0.1577 0.3633 0.038 Uiso 0.1398(16) 1 calc R U P A 2
H5C_13 H 0.8824 0.1296 0.3034 0.038 Uiso 0.1398(16) 1 calc R U P A 2
C1_14 C 0.3972(9) 0.0569(9) 0.1952(5) 0.0260(10) Uani 0.1398(16) 1 d D U P A 2
H1_14 H 0.3450 -0.0280 0.2368 0.031 Uiso 0.1398(16) 1 calc R U P A 2
C2_14 C 0.5153(13) -0.0120(13) 0.1232(7) 0.032(2) Uani 0.1398(16) 1 d D U P A 2
H2A_14 H 0.4694 -0.0829 0.1032 0.049 Uiso 0.1398(16) 1 calc R U P A 2
H2B_14 H 0.6092 -0.0672 0.1516 0.049 Uiso 0.1398(16) 1 calc R U P A 2
H2C_14 H 0.5421 0.0704 0.0690 0.049 Uiso 0.1398(16) 1 calc R U P A 2
C3_14 C 0.2707(12) 0.1781(13) 0.1467(8) 0.0330(17) Uani 0.1398(16) 1 d D U P A
2
H3A_14 H 0.2372 0.1406 0.1001 0.049 Uiso 0.1398(16) 1 calc R U P A 2
H3B_14 H 0.3119 0.2725 0.1158 0.049 Uiso 0.1398(16) 1 calc R U P A 2
H3C_14 H 0.1820 0.1989 0.1930 0.049 Uiso 0.1398(16) 1 calc R U P A 2
C1_15 C 0.4055(10) 0.0844(10) 0.3553(4) 0.0246(9) Uani 0.1398(16) 1 d D U P A 2
H1_15 H 0.4569 0.1423 0.3844 0.029 Uiso 0.1398(16) 1 calc R U P A 2
C2_15 C 0.440(2) -0.0859(13) 0.4089(9) 0.028(2) Uani 0.1398(16) 1 d D U P A 2
H2A_15 H 0.4097 -0.0958 0.4758 0.042 Uiso 0.1398(16) 1 calc R U P A 2
H2B_15 H 0.5516 -0.1251 0.3975 0.042 Uiso 0.1398(16) 1 calc R U P A 2
H2C_15 H 0.3816 -0.1448 0.3873 0.042 Uiso 0.1398(16) 1 calc R U P A 2
C3_15 C 0.2314(12) 0.1447(17) 0.3688(9) 0.028(2) Uani 0.1398(16) 1 d D U P A 2
H3A_15 H 0.1991 0.1504 0.4336 0.042 Uiso 0.1398(16) 1 calc R U P A 2
H3B_15 H 0.1751 0.0755 0.3547 0.042 Uiso 0.1398(16) 1 calc R U P A 2
H3C_15 H 0.2082 0.2470 0.3268 0.042 Uiso 0.1398(16) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1_1 B2_1 1.397(2) . ?
N1_1 C1_13 1.452(9) . ?
N1_1 C1_12 1.458(3) . ?
N1_1 C1_2 1.458(3) . ?
N1_1 C1_3 1.507(2) . ?
B2_1 C3_1 1.575(2) . ?
B2_1 C2_3 1.626(3) . ?
B2_1 C2_13 1.697(9) . ?
C3_1 C4_1 1.406(2) . ?
C3_1 C8_1 1.416(2) . ?
C4_1 C5_1 1.408(2) . ?
C4_1 C9_1 1.508(2) . ?
C5_1 C6_1 1.386(3) . ?
C5_1 C10_1 1.509(2) . ?
C6_1 C7_1 1.388(3) . ?
C6_1 H6_1 0.9500 . ?
C7_1 C8_1 1.404(2) . ?
C7_1 C11_1 1.510(2) . ?
C8_1 C12_1 1.514(2) . ?
C9_1 H9A_1 0.9800 . ?
C9_1 H9B_1 0.9800 . ?
C9_1 H9C_1 0.9800 . ?
C10_1 H10A_1 0.9800 . ?
C10_1 H10B_1 0.9800 . ?
C10_1 H10C_1 0.9800 . ?
C11_1 H11A_1 0.9800 . ?
C11_1 H11B_1 0.9800 . ?
C11_1 H11C_1 0.9800 . ?
C12_1 H12A_1 0.9800 . ?
C12_1 H12B_1 0.9800 . ?
C12_1 H12C_1 0.9800 . ?
C1_2 C2_2 1.512(3) . ?
C1_2 C3_2 1.512(3) . ?
C1_2 H1_2 1.0000 . ?
C2_2 H2A_2 0.9800 . ?
C2_2 H2B_2 0.9800 . ?
C2_2 H2C_2 0.9800 . ?
C3_2 H3A_2 0.9800 . ?
C3_2 H3B_2 0.9800 . ?
C3_2 H3C_2 0.9800 . ?
C1_12 C2_12 1.511(3) . ?
C1_12 C3_12 1.512(3) . ?
C1_12 H1_12 1.0000 . ?
C2_12 H2A_12 0.9800 . ?
C2_12 H2B_12 0.9800 . ?
C2_12 H2C_12 0.9800 . ?
C3_12 H3A_12 0.9800 . ?
C3_12 H3B_12 0.9800 . ?
C3_12 H3C_12 0.9800 . ?
C1_3 C5_3 1.522(3) . ?
C1_3 C4_3 1.520(3) . ?
C1_3 C2_3 1.582(3) . ?
C2_3 N3_3 1.450(3) . ?
C2_3 H2_3 1.0000 . ?
N3_3 C1_4 1.468(3) . ?
N3_3 C1_5 1.471(3) . ?
C4_3 H4A_3 0.9800 . ?
C4_3 H4B_3 0.9800 . ?
C4_3 H4C_3 0.9800 . ?
C5_3 H5A_3 0.9800 . ?
C5_3 H5B_3 0.9800 . ?
C5_3 H5C_3 0.9800 . ?
C1_4 C3_4 1.531(3) . ?
C1_4 C2_4 1.543(3) . ?
C1_4 H1_4 1.0000 . ?
C2_4 H2A_4 0.9800 . ?
C2_4 H2B_4 0.9800 . ?
C2_4 H2C_4 0.9800 . ?
C3_4 H3A_4 0.9800 . ?
C3_4 H3B_4 0.9800 . ?
C3_4 H3C_4 0.9800 . ?
C1_5 C3_5 1.526(3) . ?
C1_5 C2_5 1.542(3) . ?
C1_5 H1_5 1.0000 . ?
C2_5 H2A_5 0.9800 . ?
C2_5 H2B_5 0.9800 . ?
C2_5 H2C_5 0.9800 . ?
C3_5 H3A_5 0.9800 . ?
C3_5 H3B_5 0.9800 . ?
C3_5 H3C_5 0.9800 . ?
C1_13 C5_13 1.519(4) . ?
C1_13 C4_13 1.520(4) . ?
C1_13 C2_13 1.579(4) . ?
C2_13 N3_13 1.443(4) . ?
C2_13 H2_13 1.0000 . ?
N3_13 C1_15 1.465(4) . ?
N3_13 C1_14 1.465(4) . ?
C4_13 H4A_13 0.9800 . ?
C4_13 H4B_13 0.9800 . ?
C4_13 H4C_13 0.9800 . ?
C5_13 H5A_13 0.9800 . ?
C5_13 H5B_13 0.9800 . ?
C5_13 H5C_13 0.9800 . ?
C1_14 C3_14 1.530(4) . ?
C1_14 C2_14 1.544(4) . ?
C1_14 H1_14 1.0000 . ?
C2_14 H2A_14 0.9800 . ?
C2_14 H2B_14 0.9800 . ?
C2_14 H2C_14 0.9800 . ?
C3_14 H3A_14 0.9800 . ?
C3_14 H3B_14 0.9800 . ?
C3_14 H3C_14 0.9800 . ?
C1_15 C3_15 1.526(4) . ?
C1_15 C2_15 1.545(4) . ?
C1_15 H1_15 1.0000 . ?
C2_15 H2A_15 0.9800 . ?
C2_15 H2B_15 0.9800 . ?
C2_15 H2C_15 0.9800 . ?
C3_15 H3A_15 0.9800 . ?
C3_15 H3B_15 0.9800 . ?
C3_15 H3C_15 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
B2_1 N1_1 C1_13 102.6(3) . . ?
B2_1 N1_1 C1_12 137.7(3) . . ?
C1_13 N1_1 C1_12 119.1(4) . . ?
B2_1 N1_1 C1_2 140.0(2) . . ?
B2_1 N1_1 C1_3 95.62(13) . . ?
C1_2 N1_1 C1_3 124.3(2) . . ?
N1_1 B2_1 C3_1 134.14(16) . . ?
N1_1 B2_1 C2_3 90.94(13) . . ?
C3_1 B2_1 C2_3 134.22(17) . . ?
N1_1 B2_1 C2_13 83.7(3) . . ?
C3_1 B2_1 C2_13 133.7(3) . . ?
C4_1 C3_1 C8_1 119.43(14) . . ?
C4_1 C3_1 B2_1 121.55(15) . . ?
C8_1 C3_1 B2_1 118.90(14) . . ?
C3_1 C4_1 C5_1 120.34(16) . . ?
C3_1 C4_1 C9_1 120.87(14) . . ?
C5_1 C4_1 C9_1 118.79(15) . . ?
C6_1 C5_1 C4_1 118.52(16) . . ?
C6_1 C5_1 C10_1 120.53(15) . . ?
C4_1 C5_1 C10_1 120.96(16) . . ?
C5_1 C6_1 C7_1 122.99(15) . . ?
C5_1 C6_1 H6_1 118.5 . . ?
C7_1 C6_1 H6_1 118.5 . . ?
C6_1 C7_1 C8_1 118.51(16) . . ?
C6_1 C7_1 C11_1 120.29(15) . . ?
C8_1 C7_1 C11_1 121.20(16) . . ?
C7_1 C8_1 C3_1 120.21(15) . . ?
C7_1 C8_1 C12_1 119.20(15) . . ?
C3_1 C8_1 C12_1 120.59(14) . . ?
C4_1 C9_1 H9A_1 109.5 . . ?
C4_1 C9_1 H9B_1 109.5 . . ?
H9A_1 C9_1 H9B_1 109.5 . . ?
C4_1 C9_1 H9C_1 109.5 . . ?
H9A_1 C9_1 H9C_1 109.5 . . ?
H9B_1 C9_1 H9C_1 109.5 . . ?
C5_1 C10_1 H10A_1 109.5 . . ?
C5_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10B_1 109.5 . . ?
C5_1 C10_1 H10C_1 109.5 . . ?
H10A_1 C10_1 H10C_1 109.5 . . ?
H10B_1 C10_1 H10C_1 109.5 . . ?
C7_1 C11_1 H11A_1 109.5 . . ?
C7_1 C11_1 H11B_1 109.5 . . ?
H11A_1 C11_1 H11B_1 109.5 . . ?
C7_1 C11_1 H11C_1 109.5 . . ?
H11A_1 C11_1 H11C_1 109.5 . . ?
H11B_1 C11_1 H11C_1 109.5 . . ?
C8_1 C12_1 H12A_1 109.5 . . ?
C8_1 C12_1 H12B_1 109.5 . . ?
H12A_1 C12_1 H12B_1 109.5 . . ?
C8_1 C12_1 H12C_1 109.5 . . ?
H12A_1 C12_1 H12C_1 109.5 . . ?
H12B_1 C12_1 H12C_1 109.5 . . ?
N1_1 C1_2 C2_2 109.3(3) . . ?
N1_1 C1_2 C3_2 112.2(2) . . ?
C2_2 C1_2 C3_2 112.2(4) . . ?
N1_1 C1_2 H1_2 107.7 . . ?
C2_2 C1_2 H1_2 107.7 . . ?
C3_2 C1_2 H1_2 107.7 . . ?
C1_2 C2_2 H2A_2 109.5 . . ?
C1_2 C2_2 H2B_2 109.5 . . ?
H2A_2 C2_2 H2B_2 109.5 . . ?
C1_2 C2_2 H2C_2 109.5 . . ?
H2A_2 C2_2 H2C_2 109.5 . . ?
H2B_2 C2_2 H2C_2 109.5 . . ?
C1_2 C3_2 H3A_2 109.5 . . ?
C1_2 C3_2 H3B_2 109.5 . . ?
H3A_2 C3_2 H3B_2 109.5 . . ?
C1_2 C3_2 H3C_2 109.5 . . ?
H3A_2 C3_2 H3C_2 109.5 . . ?
H3B_2 C3_2 H3C_2 109.5 . . ?
N1_1 C1_12 C2_12 112.3(4) . . ?
N1_1 C1_12 C3_12 111.3(4) . . ?
C2_12 C1_12 C3_12 110.5(7) . . ?
N1_1 C1_12 H1_12 107.5 . . ?
C2_12 C1_12 H1_12 107.5 . . ?
C3_12 C1_12 H1_12 107.5 . . ?
C1_12 C2_12 H2A_12 109.5 . . ?
C1_12 C2_12 H2B_12 109.5 . . ?
H2A_12 C2_12 H2B_12 109.5 . . ?
C1_12 C2_12 H2C_12 109.5 . . ?
H2A_12 C2_12 H2C_12 109.5 . . ?
H2B_12 C2_12 H2C_12 109.5 . . ?
C1_12 C3_12 H3A_12 109.5 . . ?
C1_12 C3_12 H3B_12 109.5 . . ?
H3A_12 C3_12 H3B_12 109.5 . . ?
C1_12 C3_12 H3C_12 109.5 . . ?
H3A_12 C3_12 H3C_12 109.5 . . ?
H3B_12 C3_12 H3C_12 109.5 . . ?
N1_1 C1_3 C5_3 113.45(17) . . ?
N1_1 C1_3 C4_3 113.69(16) . . ?
C5_3 C1_3 C4_3 110.66(16) . . ?
N1_1 C1_3 C2_3 88.78(12) . . ?
C5_3 C1_3 C2_3 114.02(17) . . ?
C4_3 C1_3 C2_3 114.77(17) . . ?
N3_3 C2_3 C1_3 118.32(15) . . ?
N3_3 C2_3 B2_1 127.72(17) . . ?
C1_3 C2_3 B2_1 84.27(13) . . ?
N3_3 C2_3 H2_3 107.9 . . ?
C1_3 C2_3 H2_3 107.9 . . ?
B2_1 C2_3 H2_3 107.9 . . ?
C2_3 N3_3 C1_4 116.86(16) . . ?
C2_3 N3_3 C1_5 115.99(16) . . ?
C1_4 N3_3 C1_5 116.55(17) . . ?
C1_3 C4_3 H4A_3 109.5 . . ?
C1_3 C4_3 H4B_3 109.5 . . ?
H4A_3 C4_3 H4B_3 109.5 . . ?
C1_3 C4_3 H4C_3 109.5 . . ?
H4A_3 C4_3 H4C_3 109.5 . . ?
H4B_3 C4_3 H4C_3 109.5 . . ?
C1_3 C5_3 H5A_3 109.5 . . ?
C1_3 C5_3 H5B_3 109.5 . . ?
H5A_3 C5_3 H5B_3 109.5 . . ?
C1_3 C5_3 H5C_3 109.5 . . ?
H5A_3 C5_3 H5C_3 109.5 . . ?
H5B_3 C5_3 H5C_3 109.5 . . ?
N3_3 C1_4 C3_4 110.34(17) . . ?
N3_3 C1_4 C2_4 115.85(18) . . ?
C3_4 C1_4 C2_4 110.52(19) . . ?
N3_3 C1_4 H1_4 106.5 . . ?
C3_4 C1_4 H1_4 106.5 . . ?
C2_4 C1_4 H1_4 106.5 . . ?
C1_4 C2_4 H2A_4 109.5 . . ?
C1_4 C2_4 H2B_4 109.5 . . ?
H2A_4 C2_4 H2B_4 109.5 . . ?
C1_4 C2_4 H2C_4 109.5 . . ?
H2A_4 C2_4 H2C_4 109.5 . . ?
H2B_4 C2_4 H2C_4 109.5 . . ?
C1_4 C3_4 H3A_4 109.5 . . ?
C1_4 C3_4 H3B_4 109.5 . . ?
H3A_4 C3_4 H3B_4 109.5 . . ?
C1_4 C3_4 H3C_4 109.5 . . ?
H3A_4 C3_4 H3C_4 109.5 . . ?
H3B_4 C3_4 H3C_4 109.5 . . ?
N3_3 C1_5 C3_5 109.54(19) . . ?
N3_3 C1_5 C2_5 115.29(17) . . ?
C3_5 C1_5 C2_5 110.18(18) . . ?
N3_3 C1_5 H1_5 107.2 . . ?
C3_5 C1_5 H1_5 107.2 . . ?
C2_5 C1_5 H1_5 107.2 . . ?
C1_5 C2_5 H2A_5 109.5 . . ?
C1_5 C2_5 H2B_5 109.5 . . ?
H2A_5 C2_5 H2B_5 109.5 . . ?
C1_5 C2_5 H2C_5 109.5 . . ?
H2A_5 C2_5 H2C_5 109.5 . . ?
H2B_5 C2_5 H2C_5 109.5 . . ?
C1_5 C3_5 H3A_5 109.5 . . ?
C1_5 C3_5 H3B_5 109.5 . . ?
H3A_5 C3_5 H3B_5 109.5 . . ?
C1_5 C3_5 H3C_5 109.5 . . ?
H3A_5 C3_5 H3C_5 109.5 . . ?
H3B_5 C3_5 H3C_5 109.5 . . ?
N1_1 C1_13 C5_13 110.6(7) . . ?
N1_1 C1_13 C4_13 116.8(7) . . ?
C5_13 C1_13 C4_13 111.1(4) . . ?
N1_1 C1_13 C2_13 86.3(5) . . ?
C5_13 C1_13 C2_13 114.5(4) . . ?
C4_13 C1_13 C2_13 115.4(5) . . ?
N3_13 C2_13 C1_13 119.5(4) . . ?
N3_13 C2_13 B2_1 125.5(6) . . ?
C1_13 C2_13 B2_1 85.4(5) . . ?
N3_13 C2_13 H2_13 108.1 . . ?
C1_13 C2_13 H2_13 108.1 . . ?
B2_1 C2_13 H2_13 108.1 . . ?
C2_13 N3_13 C1_15 118.6(4) . . ?
C2_13 N3_13 C1_14 117.9(4) . . ?
C1_15 N3_13 C1_14 117.9(4) . . ?
C1_13 C4_13 H4A_13 109.5 . . ?
C1_13 C4_13 H4B_13 109.5 . . ?
H4A_13 C4_13 H4B_13 109.5 . . ?
C1_13 C4_13 H4C_13 109.5 . . ?
H4A_13 C4_13 H4C_13 109.5 . . ?
H4B_13 C4_13 H4C_13 109.5 . . ?
C1_13 C5_13 H5A_13 109.5 . . ?
C1_13 C5_13 H5B_13 109.5 . . ?
H5A_13 C5_13 H5B_13 109.5 . . ?
C1_13 C5_13 H5C_13 109.5 . . ?
H5A_13 C5_13 H5C_13 109.5 . . ?
H5B_13 C5_13 H5C_13 109.5 . . ?
N3_13 C1_14 C3_14 111.1(4) . . ?
N3_13 C1_14 C2_14 114.8(5) . . ?
C3_14 C1_14 C2_14 110.4(4) . . ?
N3_13 C1_14 H1_14 106.7 . . ?
C3_14 C1_14 H1_14 106.7 . . ?
C2_14 C1_14 H1_14 106.7 . . ?
C1_14 C2_14 H2A_14 109.5 . . ?
C1_14 C2_14 H2B_14 109.5 . . ?
H2A_14 C2_14 H2B_14 109.5 . . ?
C1_14 C2_14 H2C_14 109.5 . . ?
H2A_14 C2_14 H2C_14 109.5 . . ?
H2B_14 C2_14 H2C_14 109.5 . . ?
C1_14 C3_14 H3A_14 109.5 . . ?
C1_14 C3_14 H3B_14 109.5 . . ?
H3A_14 C3_14 H3B_14 109.5 . . ?
C1_14 C3_14 H3C_14 109.5 . . ?
H3A_14 C3_14 H3C_14 109.5 . . ?
H3B_14 C3_14 H3C_14 109.5 . . ?
N3_13 C1_15 C3_15 110.7(5) . . ?
N3_13 C1_15 C2_15 114.6(5) . . ?
C3_15 C1_15 C2_15 109.9(5) . . ?
N3_13 C1_15 H1_15 107.1 . . ?
C3_15 C1_15 H1_15 107.1 . . ?
C2_15 C1_15 H1_15 107.1 . . ?
C1_15 C2_15 H2A_15 109.5 . . ?
C1_15 C2_15 H2B_15 109.5 . . ?
H2A_15 C2_15 H2B_15 109.5 . . ?
C1_15 C2_15 H2C_15 109.5 . . ?
H2A_15 C2_15 H2C_15 109.5 . . ?
H2B_15 C2_15 H2C_15 109.5 . . ?
C1_15 C3_15 H3A_15 109.5 . . ?
C1_15 C3_15 H3B_15 109.5 . . ?
H3A_15 C3_15 H3B_15 109.5 . . ?
C1_15 C3_15 H3C_15 109.5 . . ?
H3A_15 C3_15 H3C_15 109.5 . . ?
H3B_15 C3_15 H3C_15 109.5 . . ?

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
C1_13 N1_1 B2_1 C3_1 -160.8(4) . . . . ?
C1_12 N1_1 B2_1 C3_1 8.9(4) . . . . ?
C1_2 N1_1 B2_1 C3_1 0.6(4) . . . . ?
C1_3 N1_1 B2_1 C3_1 176.0(2) . . . . ?
C1_2 N1_1 B2_1 C2_3 -170.5(3) . . . . ?
C1_3 N1_1 B2_1 C2_3 4.90(15) . . . . ?
C1_13 N1_1 B2_1 C2_13 -11.4(4) . . . . ?
C1_12 N1_1 B2_1 C2_13 158.4(4) . . . . ?
N1_1 B2_1 C3_1 C4_1 81.3(3) . . . . ?
C2_3 B2_1 C3_1 C4_1 -111.2(2) . . . . ?
C2_13 B2_1 C3_1 C4_1 -54.4(4) . . . . ?
N1_1 B2_1 C3_1 C8_1 -102.6(2) . . . . ?
C2_3 B2_1 C3_1 C8_1 64.9(3) . . . . ?
C2_13 B2_1 C3_1 C8_1 121.7(4) . . . . ?
C8_1 C3_1 C4_1 C5_1 -0.8(3) . . . . ?
B2_1 C3_1 C4_1 C5_1 175.29(17) . . . . ?
C8_1 C3_1 C4_1 C9_1 179.94(16) . . . . ?
B2_1 C3_1 C4_1 C9_1 -4.0(3) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.5(3) . . . . ?
C9_1 C4_1 C5_1 C6_1 179.76(17) . . . . ?
C3_1 C4_1 C5_1 C10_1 -179.54(17) . . . . ?
C9_1 C4_1 C5_1 C10_1 -0.2(3) . . . . ?
C4_1 C5_1 C6_1 C7_1 -0.2(3) . . . . ?
C10_1 C5_1 C6_1 C7_1 179.80(17) . . . . ?
C5_1 C6_1 C7_1 C8_1 0.3(3) . . . . ?
C5_1 C6_1 C7_1 C11_1 -179.39(17) . . . . ?
C6_1 C7_1 C8_1 C3_1 -0.6(3) . . . . ?
C11_1 C7_1 C8_1 C3_1 179.07(16) . . . . ?
C6_1 C7_1 C8_1 C12_1 178.97(16) . . . . ?
C11_1 C7_1 C8_1 C12_1 -1.4(3) . . . . ?
C4_1 C3_1 C8_1 C7_1 0.8(3) . . . . ?
B2_1 C3_1 C8_1 C7_1 -175.34(16) . . . . ?
C4_1 C3_1 C8_1 C12_1 -178.70(16) . . . . ?
B2_1 C3_1 C8_1 C12_1 5.1(2) . . . . ?
B2_1 N1_1 C1_2 C2_2 29.9(5) . . . . ?
C1_3 N1_1 C1_2 C2_2 -144.5(4) . . . . ?
B2_1 N1_1 C1_2 C3_2 -95.1(4) . . . . ?
C1_3 N1_1 C1_2 C3_2 90.4(4) . . . . ?
B2_1 N1_1 C1_12 C2_12 78.5(6) . . . . ?
C1_13 N1_1 C1_12 C2_12 -113.0(7) . . . . ?
B2_1 N1_1 C1_12 C3_12 -46.0(7) . . . . ?
C1_13 N1_1 C1_12 C3_12 122.5(7) . . . . ?
B2_1 N1_1 C1_3 C5_3 -120.80(18) . . . . ?
C1_2 N1_1 C1_3 C5_3 55.6(3) . . . . ?
B2_1 N1_1 C1_3 C4_3 111.59(17) . . . . ?
C1_2 N1_1 C1_3 C4_3 -72.0(3) . . . . ?
B2_1 N1_1 C1_3 C2_3 -5.04(15) . . . . ?
C1_2 N1_1 C1_3 C2_3 171.4(2) . . . . ?
N1_1 C1_3 C2_3 N3_3 134.45(16) . . . . ?
C5_3 C1_3 C2_3 N3_3 -110.3(2) . . . . ?
C4_3 C1_3 C2_3 N3_3 18.8(2) . . . . ?
N1_1 C1_3 C2_3 B2_1 4.33(13) . . . . ?
C5_3 C1_3 C2_3 B2_1 119.56(17) . . . . ?
C4_3 C1_3 C2_3 B2_1 -111.32(17) . . . . ?
N1_1 B2_1 C2_3 N3_3 -126.36(19) . . . . ?
C3_1 B2_1 C2_3 N3_3 62.6(3) . . . . ?
N1_1 B2_1 C2_3 C1_3 -4.67(14) . . . . ?
C3_1 B2_1 C2_3 C1_3 -175.7(2) . . . . ?
C1_3 C2_3 N3_3 C1_4 -89.3(2) . . . . ?
B2_1 C2_3 N3_3 C1_4 16.5(3) . . . . ?
C1_3 C2_3 N3_3 C1_5 127.12(19) . . . . ?
B2_1 C2_3 N3_3 C1_5 -127.0(2) . . . . ?
C2_3 N3_3 C1_4 C3_4 141.55(19) . . . . ?
C1_5 N3_3 C1_4 C3_4 -75.1(2) . . . . ?
C2_3 N3_3 C1_4 C2_4 -91.9(2) . . . . ?
C1_5 N3_3 C1_4 C2_4 51.4(2) . . . . ?
C2_3 N3_3 C1_5 C3_5 -74.1(2) . . . . ?
C1_4 N3_3 C1_5 C3_5 142.3(2) . . . . ?
C2_3 N3_3 C1_5 C2_5 50.8(3) . . . . ?
C1_4 N3_3 C1_5 C2_5 -92.8(2) . . . . ?
B2_1 N1_1 C1_13 C5_13 -102.7(5) . . . . ?
C1_12 N1_1 C1_13 C5_13 85.2(5) . . . . ?
B2_1 N1_1 C1_13 C4_13 128.9(5) . . . . ?
C1_12 N1_1 C1_13 C4_13 -43.2(6) . . . . ?
B2_1 N1_1 C1_13 C2_13 12.2(4) . . . . ?
C1_12 N1_1 C1_13 C2_13 -159.9(4) . . . . ?
N1_1 C1_13 C2_13 N3_13 -138.3(6) . . . . ?
C5_13 C1_13 C2_13 N3_13 -27.3(9) . . . . ?
C4_13 C1_13 C2_13 N3_13 103.6(8) . . . . ?
N1_1 C1_13 C2_13 B2_1 -9.8(3) . . . . ?
C5_13 C1_13 C2_13 B2_1 101.3(7) . . . . ?
C4_13 C1_13 C2_13 B2_1 -127.8(7) . . . . ?
N1_1 B2_1 C2_13 N3_13 133.5(6) . . . . ?
C3_1 B2_1 C2_13 N3_13 -76.8(7) . . . . ?
N1_1 B2_1 C2_13 C1_13 10.2(3) . . . . ?
C3_1 B2_1 C2_13 C1_13 159.9(4) . . . . ?
C1_13 C2_13 N3_13 C1_15 84.6(9) . . . . ?
B2_1 C2_13 N3_13 C1_15 -22.2(9) . . . . ?
C1_13 C2_13 N3_13 C1_14 -122.3(8) . . . . ?
B2_1 C2_13 N3_13 C1_14 130.9(6) . . . . ?
C2_13 N3_13 C1_14 C3_14 -57.1(9) . . . . ?
C1_15 N3_13 C1_14 C3_14 96.2(8) . . . . ?
C2_13 N3_13 C1_14 C2_14 69.0(9) . . . . ?
C1_15 N3_13 C1_14 C2_14 -137.6(8) . . . . ?
C2_13 N3_13 C1_15 C3_15 95.3(9) . . . . ?
C1_14 N3_13 C1_15 C3_15 -57.9(10) . . . . ?
C2_13 N3_13 C1_15 C2_15 -139.7(10) . . . . ?
C1_14 N3_13 C1_15 C2_15 67.2(11) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039

_shelxl_version_number           2014/6

