# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_syg2d
_database_code_depnum_ccdc_archive 'CCDC 1590109'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H37 B N2'
_chemical_formula_weight         484.46

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      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                   22.653(2)
_cell_length_b                   8.3251(7)
_cell_length_c                   15.2916(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.682(3)
_cell_angle_gamma                90
_cell_volume                     2747.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2779
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      24.44

_exptl_crystal_description       Block
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25922
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_av_R_equivalents  0.1291
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         27.122
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6057
_reflns_number_gt                3294
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0500P)²+1.0000P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6057
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.003
_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 N 0.44989(9) -0.0321(2) 0.85727(13) 0.0310(5) Uani 1 1 d . . . . .
N2 N 0.39222(9) -0.0516(2) 0.49146(13) 0.0298(5) Uani 1 1 d . . . . .
C1 C 0.25069(10) 0.2008(3) 0.56718(15) 0.0274(5) Uani 1 1 d . . . . .
C2 C 0.25107(11) 0.1852(3) 0.47732(16) 0.0329(6) Uani 1 1 d . . . . .
H2 H 0.2178 0.2301 0.4299 0.039 Uiso 1 1 calc R U . . .
C3 C 0.29790(11) 0.1070(3) 0.45328(16) 0.0323(6) Uani 1 1 d . . . . .
H3 H 0.2961 0.1018 0.3905 0.039 Uiso 1 1 calc R U . . .
C4 C 0.34710(10) 0.0363(3) 0.51871(15) 0.0259(5) Uani 1 1 d . . . . .
C5 C 0.35198(10) 0.0534(3) 0.61432(15) 0.0246(5) Uani 1 1 d . . . . .
C6 C 0.30219(10) 0.1328(2) 0.63622(15) 0.0248(5) Uani 1 1 d . . . . .
C7 C 0.30275(11) 0.1387(3) 0.73030(15) 0.0292(6) Uani 1 1 d . . . . .
H7 H 0.2686 0.1863 0.7443 0.035 Uiso 1 1 calc R U . . .
C8 C 0.34944(11) 0.0799(3) 0.79898(16) 0.0295(6) Uani 1 1 d . . . . .
H8 H 0.3470 0.0820 0.8599 0.035 Uiso 1 1 calc R U . . .
C9 C 0.40281(10) 0.0141(3) 0.78170(15) 0.0260(5) Uani 1 1 d . . . . .
C10 C 0.40538(10) 0.0030(3) 0.69046(15) 0.0257(5) Uani 1 1 d . . . . .
C11 C 0.46301(11) -0.0482(3) 0.68280(16) 0.0334(6) Uani 1 1 d . . . . .
H11 H 0.4689 -0.0538 0.6240 0.040 Uiso 1 1 calc R U . . .
C12 C 0.51038(12) -0.0896(3) 0.75882(17) 0.0384(6) Uani 1 1 d . . . . .
H12 H 0.5491 -0.1220 0.7525 0.046 Uiso 1 1 calc R U . . .
C13 C 0.50235(11) -0.0848(3) 0.84610(16) 0.0318(6) Uani 1 1 d . . . . .
C14 C 0.55181(11) -0.1381(3) 0.93045(16) 0.0383(6) Uani 1 1 d . . . . .
H14A H 0.5474 -0.2534 0.9397 0.057 Uiso 1 1 calc R U . . .
H14B H 0.5478 -0.0789 0.9837 0.057 Uiso 1 1 calc R U . . .
H14C H 0.5926 -0.1169 0.9231 0.057 Uiso 1 1 calc R U . . .
C15 C 0.39770(12) -0.0175(3) 0.40042(16) 0.0430(7) Uani 1 1 d . . . . .
H15A H 0.3614 -0.0600 0.3534 0.065 Uiso 1 1 calc R U . . .
H15B H 0.4352 -0.0686 0.3943 0.065 Uiso 1 1 calc R U . . .
H15C H 0.4002 0.0989 0.3925 0.065 Uiso 1 1 calc R U . . .
C16 C 0.39159(13) -0.2251(3) 0.5067(2) 0.0475(7) Uani 1 1 d . . . . .
H16A H 0.3550 -0.2724 0.4623 0.071 Uiso 1 1 calc R U . . .
H16B H 0.3902 -0.2459 0.5691 0.071 Uiso 1 1 calc R U . . .
H16C H 0.4291 -0.2733 0.4988 0.071 Uiso 1 1 calc R U . . .
C17 C 0.12881(10) 0.2472(3) 0.51602(15) 0.0256(5) Uani 1 1 d . . . . .
C18 C 0.08649(10) 0.3653(3) 0.46776(16) 0.0280(5) Uani 1 1 d . . . . .
C19 C 0.09837(12) 0.5434(3) 0.48522(17) 0.0387(7) Uani 1 1 d . . . . .
H19A H 0.1421 0.5666 0.4933 0.058 Uiso 1 1 calc R U . . .
H19B H 0.0883 0.5743 0.5409 0.058 Uiso 1 1 calc R U . . .
H19C H 0.0724 0.6045 0.4328 0.058 Uiso 1 1 calc R U . . .
C20 C 0.03213(11) 0.3207(3) 0.40175(16) 0.0352(6) Uani 1 1 d . . . . .
H20 H 0.0050 0.4024 0.3692 0.042 Uiso 1 1 calc R U . . .
C21 C 0.01582(11) 0.1616(3) 0.38145(17) 0.0376(6) Uani 1 1 d . . . . .
C22 C -0.04259(13) 0.1166(4) 0.3073(2) 0.0620(9) Uani 1 1 d . . . . .
H22A H -0.0759 0.1908 0.3087 0.093 Uiso 1 1 calc R U . . .
H22B H -0.0545 0.0067 0.3176 0.093 Uiso 1 1 calc R U . . .
H22C H -0.0354 0.1230 0.2474 0.093 Uiso 1 1 calc R U . . .
C23 C 0.05557(12) 0.0454(3) 0.43212(17) 0.0386(7) Uani 1 1 d . . . . .
H23 H 0.0443 -0.0644 0.4217 0.046 Uiso 1 1 calc R U . . .
C24 C 0.11122(11) 0.0836(3) 0.49751(16) 0.0327(6) Uani 1 1 d . . . . .
C25 C 0.15059(13) -0.0523(3) 0.54947(19) 0.0481(8) Uani 1 1 d . . . . .
H25A H 0.1241 -0.1444 0.5515 0.072 Uiso 1 1 calc R U . . .
H25B H 0.1724 -0.0172 0.6122 0.072 Uiso 1 1 calc R U . . .
H25C H 0.1809 -0.0835 0.5185 0.072 Uiso 1 1 calc R U . . .
C26 C 0.20121(10) 0.4232(3) 0.66037(15) 0.0247(5) Uani 1 1 d . . . . .
C27 C 0.24294(10) 0.5528(3) 0.66899(15) 0.0290(6) Uani 1 1 d . . . . .
C28 C 0.28742(13) 0.5652(3) 0.61281(19) 0.0470(7) Uani 1 1 d . . . . .
H28A H 0.2672 0.5254 0.5506 0.071 Uiso 1 1 calc R U . . .
H28B H 0.3244 0.5006 0.6416 0.071 Uiso 1 1 calc R U . . .
H28C H 0.2994 0.6777 0.6099 0.071 Uiso 1 1 calc R U . . .
C29 C 0.24371(11) 0.6787(3) 0.72940(16) 0.0314(6) Uani 1 1 d . . . . .
H29 H 0.2713 0.7659 0.7326 0.038 Uiso 1 1 calc R U . . .
C30 C 0.20569(11) 0.6806(3) 0.78453(16) 0.0332(6) Uani 1 1 d . . . . .
C31 C 0.20733(14) 0.8175(3) 0.84992(19) 0.0553(8) Uani 1 1 d . . . . .
H31A H 0.2395 0.8944 0.8471 0.083 Uiso 1 1 calc R U . . .
H31B H 0.2166 0.7756 0.9125 0.083 Uiso 1 1 calc R U . . .
H31C H 0.1670 0.8715 0.8326 0.083 Uiso 1 1 calc R U . . .
C32 C 0.16602(11) 0.5510(3) 0.77902(16) 0.0346(6) Uani 1 1 d . . . . .
H32 H 0.1404 0.5484 0.8180 0.042 Uiso 1 1 calc R U . . .
C33 C 0.16271(11) 0.4248(3) 0.71799(15) 0.0296(6) Uani 1 1 d . . . . .
C34 C 0.11867(13) 0.2880(3) 0.71782(19) 0.0447(7) Uani 1 1 d . . . . .
H34A H 0.0829 0.2943 0.6625 0.067 Uiso 1 1 calc R U . . .
H34B H 0.1046 0.2957 0.7723 0.067 Uiso 1 1 calc R U . . .
H34C H 0.1400 0.1854 0.7186 0.067 Uiso 1 1 calc R U . . .
B1 B 0.19425(13) 0.2898(3) 0.58460(18) 0.0272(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.326(3) . ?
N1 C9 1.368(3) . ?
N2 C4 1.419(3) . ?
N2 C15 1.462(3) . ?
N2 C16 1.464(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.431(3) . ?
C1 B1 1.569(4) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.439(3) . ?
C5 C6 1.432(3) . ?
C5 C10 1.463(3) . ?
C6 C7 1.436(3) . ?
C7 C8 1.337(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.423(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(3) . ?
C10 C11 1.412(3) . ?
C11 C12 1.365(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.496(3) . ?
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 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.414(3) . ?
C17 C24 1.424(3) . ?
C17 B1 1.574(3) . ?
C18 C20 1.385(3) . ?
C18 C19 1.517(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C23 1.387(3) . ?
C21 C22 1.505(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.508(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.414(3) . ?
C26 C33 1.416(3) . ?
C26 B1 1.578(3) . ?
C27 C29 1.394(3) . ?
C27 C28 1.513(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.376(3) . ?
C29 H29 0.9500 . ?
C30 C32 1.390(3) . ?
C30 C31 1.509(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.392(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.514(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C13 N1 C9 118.9(2) . . ?
C4 N2 C15 117.18(19) . . ?
C4 N2 C16 114.80(19) . . ?
C15 N2 C16 110.5(2) . . ?
C2 C1 C6 116.5(2) . . ?
C2 C1 B1 117.7(2) . . ?
C6 C1 B1 125.8(2) . . ?
C1 C2 C3 122.9(2) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 N2 120.1(2) . . ?
C3 C4 C5 119.3(2) . . ?
N2 C4 C5 120.6(2) . . ?
C6 C5 C4 117.4(2) . . ?
C6 C5 C10 117.8(2) . . ?
C4 C5 C10 124.7(2) . . ?
C1 C6 C5 122.2(2) . . ?
C1 C6 C7 118.9(2) . . ?
C5 C6 C7 118.8(2) . . ?
C8 C7 C6 122.6(2) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
N1 C9 C10 124.0(2) . . ?
N1 C9 C8 116.1(2) . . ?
C10 C9 C8 119.9(2) . . ?
C11 C10 C9 114.6(2) . . ?
C11 C10 C5 125.6(2) . . ?
C9 C10 C5 119.6(2) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
N1 C13 C12 120.9(2) . . ?
N1 C13 C14 116.9(2) . . ?
C12 C13 C14 122.2(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 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C24 117.2(2) . . ?
C18 C17 B1 122.90(19) . . ?
C24 C17 B1 119.9(2) . . ?
C20 C18 C17 120.4(2) . . ?
C20 C18 C19 117.5(2) . . ?
C17 C18 C19 122.1(2) . . ?
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 . . ?
C18 C20 C21 122.5(2) . . ?
C18 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C23 117.3(2) . . ?
C20 C21 C22 121.4(2) . . ?
C23 C21 C22 121.4(2) . . ?
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 C24 122.5(2) . . ?
C21 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C23 C24 C17 120.0(2) . . ?
C23 C24 C25 118.1(2) . . ?
C17 C24 C25 121.8(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 . . ?
C27 C26 C33 117.1(2) . . ?
C27 C26 B1 121.4(2) . . ?
C33 C26 B1 121.4(2) . . ?
C29 C27 C26 120.6(2) . . ?
C29 C27 C28 116.6(2) . . ?
C26 C27 C28 122.7(2) . . ?
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 C27 122.1(2) . . ?
C30 C29 H29 119.0 . . ?
C27 C29 H29 119.0 . . ?
C29 C30 C32 117.8(2) . . ?
C29 C30 C31 121.4(2) . . ?
C32 C30 C31 120.8(2) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 C33 121.9(2) . . ?
C30 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C32 C33 C26 120.5(2) . . ?
C32 C33 C34 118.1(2) . . ?
C26 C33 C34 121.5(2) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C1 B1 C17 115.6(2) . . ?
C1 B1 C26 123.5(2) . . ?
C17 B1 C26 120.8(2) . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_sy23
_database_code_depnum_ccdc_archive 'CCDC 1590116'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.66 H4.11 B0.11 N0.11 S0.11'
_chemical_formula_weight         54.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 '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                   7.9250(4)
_cell_length_b                   21.8524(8)
_cell_length_c                   16.0075(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.766(2)
_cell_angle_gamma                90
_cell_volume                     2739.8(2)
_cell_formula_units_Z            35
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.34

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60597
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         27.130
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6043
_reflns_number_gt                4049
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+2.9000P] 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         6043
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2442
_refine_ls_wR_factor_gt          0.2213
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.124
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.4588(4) 0.73267(15) 0.5382(2) 0.0292(7) Uani 1 1 d . . . . .
S1 S 0.6085(2) 0.55619(5) 0.75854(7) 0.0790(5) Uani 1 1 d . . . . .
N1 N -0.0057(4) 0.57439(13) 0.32242(18) 0.0431(7) Uani 1 1 d . . . . .
C1 C 0.3375(4) 0.68637(13) 0.48542(18) 0.0301(6) Uani 1 1 d . . . . .
C2 C 0.3097(4) 0.62403(13) 0.50509(18) 0.0281(6) Uani 1 1 d . . . . .
C3 C 0.1962(4) 0.58790(13) 0.4507(2) 0.0331(7) Uani 1 1 d . . . . .
H3 H 0.1773 0.5472 0.4661 0.040 Uiso 1 1 calc R U . . .
C4 C 0.1091(4) 0.61037(14) 0.37355(19) 0.0320(7) Uani 1 1 d . . . . .
C5 C 0.1400(4) 0.67138(14) 0.3529(2) 0.0366(7) Uani 1 1 d . . . . .
H5 H 0.0870 0.6878 0.3012 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2473(4) 0.70693(14) 0.4078(2) 0.0365(7) Uani 1 1 d . . . . .
H6 H 0.2618 0.7480 0.3928 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3955(4) 0.59679(13) 0.58435(19) 0.0315(7) Uani 1 1 d . . . . .
H7 H 0.4327 0.6240 0.6288 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4257(4) 0.53781(14) 0.5996(2) 0.0345(7) Uani 1 1 d . . . . .
H8 H 0.3878 0.5102 0.5556 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5125(4) 0.51219(14) 0.67840(19) 0.0334(7) Uani 1 1 d . . . . .
C10 C 0.5214(4) 0.44530(12) 0.70148(18) 0.0320(7) Uani 1 1 d . . . . .
H10A H 0.4697 0.4125 0.6692 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6254(5) 0.44227(18) 0.7832(3) 0.0571(10) Uani 1 1 d . . . . .
H11 H 0.6567 0.4048 0.8099 0.069 Uiso 1 1 calc R U . . .
C12 C 0.6749(6) 0.4960(2) 0.8187(2) 0.0619(11) Uani 1 1 d . . . . .
H12 H 0.7408 0.4994 0.8726 0.074 Uiso 1 1 calc R U . . .
C13 C -0.0159(6) 0.50971(17) 0.3379(3) 0.0566(10) Uani 1 1 d . . . . .
H13A H -0.0995 0.4913 0.2946 0.085 Uiso 1 1 calc R U . . .
H13B H -0.0499 0.5031 0.3929 0.085 Uiso 1 1 calc R U . . .
H13C H 0.0948 0.4911 0.3367 0.085 Uiso 1 1 calc R U . . .
C14 C -0.0919(5) 0.59747(19) 0.2425(3) 0.0592(11) Uani 1 1 d . . . . .
H14A H -0.0097 0.6031 0.2040 0.089 Uiso 1 1 calc R U . . .
H14B H -0.1455 0.6363 0.2514 0.089 Uiso 1 1 calc R U . . .
H14C H -0.1784 0.5684 0.2184 0.089 Uiso 1 1 calc R U . . .
C15 C 0.6277(4) 0.71289(13) 0.59813(18) 0.0301(6) Uani 1 1 d . . . . .
C16 C 0.6629(4) 0.73220(14) 0.68373(19) 0.0340(7) Uani 1 1 d . . . . .
C17 C 0.5391(5) 0.7716(2) 0.7227(2) 0.0560(10) Uani 1 1 d . . . . .
H17A H 0.5092 0.8072 0.6873 0.084 Uiso 1 1 calc R U . . .
H17B H 0.5918 0.7847 0.7785 0.084 Uiso 1 1 calc R U . . .
H17C H 0.4369 0.7482 0.7272 0.084 Uiso 1 1 calc R U . . .
C18 C 0.8102(4) 0.71251(14) 0.73525(19) 0.0379(8) Uani 1 1 d . . . . .
H18 H 0.8302 0.7255 0.7919 0.045 Uiso 1 1 calc R U . . .
C19 C 0.9287(4) 0.67444(14) 0.7060(2) 0.0393(8) Uani 1 1 d . . . . .
C20 C 1.0881(5) 0.65373(19) 0.7630(3) 0.0618(12) Uani 1 1 d . . . . .
H20A H 1.1349 0.6181 0.7385 0.093 Uiso 1 1 calc R U . . .
H20B H 1.0601 0.6433 0.8181 0.093 Uiso 1 1 calc R U . . .
H20C H 1.1718 0.6865 0.7688 0.093 Uiso 1 1 calc R U . . .
C21 C 0.8955(4) 0.65667(14) 0.6218(2) 0.0351(7) Uani 1 1 d . . . . .
H21 H 0.9751 0.6315 0.6004 0.042 Uiso 1 1 calc R U . . .
C22 C 0.7503(4) 0.67445(13) 0.56824(19) 0.0314(7) Uani 1 1 d . . . . .
C23 C 0.7316(5) 0.65261(18) 0.4780(2) 0.0487(9) Uani 1 1 d . . . . .
H23A H 0.6538 0.6794 0.4423 0.073 Uiso 1 1 calc R U . . .
H23B H 0.6868 0.6112 0.4744 0.073 Uiso 1 1 calc R U . . .
H23C H 0.8423 0.6532 0.4591 0.073 Uiso 1 1 calc R U . . .
C24 C 0.4038(4) 0.80270(13) 0.52376(18) 0.0298(6) Uani 1 1 d . . . . .
C25 C 0.2413(4) 0.82260(13) 0.53778(19) 0.0334(7) Uani 1 1 d . . . . .
C26 C 0.1251(5) 0.78189(16) 0.5811(3) 0.0503(9) Uani 1 1 d . . . . .
H26A H 0.0436 0.7616 0.5388 0.076 Uiso 1 1 calc R U . . .
H26B H 0.0645 0.8067 0.6171 0.076 Uiso 1 1 calc R U . . .
H26C H 0.1933 0.7515 0.6152 0.076 Uiso 1 1 calc R U . . .
C27 C 0.1821(4) 0.88077(14) 0.5123(2) 0.0380(7) Uani 1 1 d . . . . .
H27 H 0.0741 0.8934 0.5230 0.046 Uiso 1 1 calc R U . . .
C28 C 0.2786(5) 0.92026(14) 0.4717(2) 0.0398(8) Uani 1 1 d . . . . .
C29 C 0.2085(6) 0.98145(16) 0.4375(3) 0.0617(11) Uani 1 1 d . . . . .
H29A H 0.3023 1.0094 0.4344 0.093 Uiso 1 1 calc R U . . .
H29B H 0.1346 0.9982 0.4749 0.093 Uiso 1 1 calc R U . . .
H29C H 0.1438 0.9758 0.3816 0.093 Uiso 1 1 calc R U . . .
C30 C 0.4393(5) 0.90136(15) 0.4603(2) 0.0433(8) Uani 1 1 d . . . . .
H30 H 0.5077 0.9283 0.4342 0.052 Uiso 1 1 calc R U . . .
C31 C 0.5048(4) 0.84386(15) 0.4858(2) 0.0384(7) Uani 1 1 d . . . . .
C32 C 0.6805(5) 0.8275(2) 0.4685(3) 0.0703(13) Uani 1 1 d . . . . .
H32A H 0.6741 0.7909 0.4339 0.105 Uiso 1 1 calc R U . . .
H32B H 0.7546 0.8200 0.5216 0.105 Uiso 1 1 calc R U . . .
H32C H 0.7259 0.8609 0.4389 0.105 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
B1 C1 1.554(4) . ?
B1 C15 1.583(4) . ?
B1 C24 1.598(4) . ?
S1 C12 1.668(4) . ?
S1 C9 1.689(3) . ?
N1 C4 1.375(4) . ?
N1 C13 1.439(5) . ?
N1 C14 1.446(5) . ?
C1 C6 1.409(4) . ?
C1 C2 1.423(4) . ?
C2 C3 1.397(4) . ?
C2 C7 1.471(4) . ?
C3 C4 1.408(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.404(4) . ?
C5 C6 1.368(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.327(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.454(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.507(4) . ?
C10 C11 1.437(5) . ?
C10 H10A 0.9400 . ?
C11 C12 1.337(6) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.420(4) . ?
C15 C22 1.421(4) . ?
C16 C18 1.391(5) . ?
C16 C17 1.509(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 C19 1.388(5) . ?
C18 H18 0.9400 . ?
C19 C21 1.389(5) . ?
C19 C20 1.510(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.507(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 C31 1.402(4) . ?
C24 C25 1.410(4) . ?
C25 C27 1.394(4) . ?
C25 C26 1.521(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 C28 1.379(5) . ?
C27 H27 0.9400 . ?
C28 C30 1.377(5) . ?
C28 C29 1.517(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C30 C31 1.397(5) . ?
C30 H30 0.9400 . ?
C31 C32 1.504(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 C15 123.2(3) . . ?
C1 B1 C24 114.4(3) . . ?
C15 B1 C24 122.4(3) . . ?
C12 S1 C9 93.17(19) . . ?
C4 N1 C13 120.6(3) . . ?
C4 N1 C14 120.5(3) . . ?
C13 N1 C14 117.6(3) . . ?
C6 C1 C2 115.2(3) . . ?
C6 C1 B1 117.4(3) . . ?
C2 C1 B1 127.4(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 C7 118.6(3) . . ?
C1 C2 C7 120.8(3) . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
N1 C4 C5 121.8(3) . . ?
N1 C4 C3 120.9(3) . . ?
C5 C4 C3 117.3(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 124.6(3) . . ?
C5 C6 H6 117.7 . . ?
C1 C6 H6 117.7 . . ?
C8 C7 C2 126.8(3) . . ?
C8 C7 H7 116.6 . . ?
C2 C7 H7 116.6 . . ?
C7 C8 C9 125.6(3) . . ?
C7 C8 H8 117.2 . . ?
C9 C8 H8 117.2 . . ?
C8 C9 C10 125.8(3) . . ?
C8 C9 S1 122.6(2) . . ?
C10 C9 S1 111.6(2) . . ?
C11 C10 C9 105.5(3) . . ?
C11 C10 H10A 127.3 . . ?
C9 C10 H10A 127.3 . . ?
C12 C11 C10 116.0(3) . . ?
C12 C11 H11 122.0 . . ?
C10 C11 H11 122.0 . . ?
C11 C12 S1 113.6(3) . . ?
C11 C12 H12 123.2 . . ?
S1 C12 H12 123.2 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C22 117.2(3) . . ?
C16 C15 B1 121.8(3) . . ?
C22 C15 B1 121.0(3) . . ?
C18 C16 C15 120.3(3) . . ?
C18 C16 C17 118.1(3) . . ?
C15 C16 C17 121.6(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 . . ?
C19 C18 C16 122.4(3) . . ?
C19 C18 H18 118.8 . . ?
C16 C18 H18 118.8 . . ?
C18 C19 C21 117.2(3) . . ?
C18 C19 C20 121.5(3) . . ?
C21 C19 C20 121.3(3) . . ?
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 C19 122.7(3) . . ?
C22 C21 H21 118.6 . . ?
C19 C21 H21 118.6 . . ?
C21 C22 C15 120.3(3) . . ?
C21 C22 C23 117.2(3) . . ?
C15 C22 C23 122.5(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C31 C24 C25 117.8(3) . . ?
C31 C24 B1 121.1(3) . . ?
C25 C24 B1 120.5(3) . . ?
C27 C25 C24 120.6(3) . . ?
C27 C25 C26 117.8(3) . . ?
C24 C25 C26 121.6(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C25 121.5(3) . . ?
C28 C27 H27 119.2 . . ?
C25 C27 H27 119.2 . . ?
C30 C28 C27 117.7(3) . . ?
C30 C28 C29 120.8(3) . . ?
C27 C28 C29 121.5(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 C31 122.7(3) . . ?
C28 C30 H30 118.6 . . ?
C31 C30 H30 118.6 . . ?
C30 C31 C24 119.5(3) . . ?
C30 C31 C32 118.3(3) . . ?
C24 C31 C32 122.2(3) . . ?
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 . . ?

_refine_diff_density_max         0.854
_refine_diff_density_min         -1.096
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_sy2c
_database_code_depnum_ccdc_archive 'CCDC 1590115'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.43 H2.79 B0.07 N0.14'
_chemical_formula_weight         34.75

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                   10.294(3)
_cell_length_b                   11.896(4)
_cell_length_c                   13.128(5)
_cell_angle_alpha                66.239(11)
_cell_angle_beta                 88.621(11)
_cell_angle_gamma                75.243(12)
_cell_volume                     1417.2(8)
_cell_formula_units_Z            28
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4489
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      24.49

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19796
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         2.419
_diffrn_reflns_theta_max         27.261
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6268
_reflns_number_gt                3597
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1071P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.089(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6268
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.2045
_refine_ls_wR_factor_gt          0.1647
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 N 0.09486(19) 0.65605(18) 0.41559(15) 0.0431(5) Uani 1 1 d . . . . .
N2 N 0.3366(2) 0.17052(18) 0.76519(18) 0.0524(6) Uani 1 1 d . . . . .
C1 C 0.2795(2) 0.53774(19) 0.76667(16) 0.0331(5) Uani 1 1 d . . . . .
C2 C 0.4034(2) 0.4541(2) 0.78099(17) 0.0363(5) Uani 1 1 d . . . . .
H2 H 0.4805 0.4830 0.7842 0.044 Uiso 1 1 calc R U . . .
C3 C 0.4254(2) 0.3263(2) 0.79151(19) 0.0404(6) Uani 1 1 d . . . . .
H3 H 0.5102 0.2663 0.8221 0.048 Uiso 1 1 calc R U . . .
C4 C 0.3242(2) 0.2905(2) 0.75753(18) 0.0379(5) Uani 1 1 d . . . . .
C5 C 0.1941(2) 0.3926(2) 0.70385(17) 0.0354(5) Uani 1 1 d . . . . .
H5 H 0.1198 0.3499 0.7133 0.042 Uiso 1 1 calc R U . . .
C6 C 0.1600(2) 0.4853(2) 0.76166(18) 0.0355(5) Uani 1 1 d . . . . .
H6 H 0.1414 0.4365 0.8401 0.043 Uiso 1 1 calc R U . . .
C7 C 0.0320(2) 0.5870(2) 0.7020(2) 0.0420(6) Uani 1 1 d . . . . .
H7 H -0.0309 0.6202 0.7437 0.050 Uiso 1 1 calc R U . . .
C8 C 0.0062(2) 0.6305(2) 0.5926(2) 0.0440(6) Uani 1 1 d . . . . .
H8 H -0.0754 0.6935 0.5570 0.053 Uiso 1 1 calc R U . . .
C9 C 0.1025(2) 0.5826(2) 0.52559(18) 0.0369(5) Uani 1 1 d . . . . .
C10 C 0.2001(2) 0.4675(2) 0.57927(18) 0.0351(5) Uani 1 1 d . . . . .
C11 C 0.2950(2) 0.4274(2) 0.51586(19) 0.0429(6) Uani 1 1 d . . . . .
H11 H 0.3632 0.3493 0.5493 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2888(3) 0.5031(2) 0.4030(2) 0.0481(6) Uani 1 1 d . . . . .
H12 H 0.3535 0.4774 0.3583 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1891(3) 0.6157(2) 0.35535(19) 0.0467(6) Uani 1 1 d . . . . .
C14 C 0.1798(3) 0.7027(3) 0.2340(2) 0.0685(8) Uani 1 1 d . . . . .
H14A H 0.2191 0.6527 0.1916 0.103 Uiso 1 1 calc R U . . .
H14B H 0.2293 0.7660 0.2246 0.103 Uiso 1 1 calc R U . . .
H14C H 0.0850 0.7462 0.2065 0.103 Uiso 1 1 calc R U . . .
C15 C 0.2427(3) 0.1346(2) 0.7125(2) 0.0554(7) Uani 1 1 d . . . . .
H15A H 0.1672 0.2091 0.6724 0.083 Uiso 1 1 calc R U . . .
H15B H 0.2086 0.0681 0.7695 0.083 Uiso 1 1 calc R U . . .
H15C H 0.2884 0.1020 0.6597 0.083 Uiso 1 1 calc R U . . .
C16 C 0.4616(3) 0.0730(3) 0.8192(3) 0.0780(10) Uani 1 1 d . . . . .
H16A H 0.5349 0.0904 0.7711 0.117 Uiso 1 1 calc R U . . .
H16B H 0.4507 -0.0109 0.8317 0.117 Uiso 1 1 calc R U . . .
H16C H 0.4834 0.0741 0.8910 0.117 Uiso 1 1 calc R U . . .
C17 C 0.3928(2) 0.72571(19) 0.73423(17) 0.0335(5) Uani 1 1 d . . . . .
C18 C 0.4268(2) 0.7617(2) 0.62290(18) 0.0364(5) Uani 1 1 d . . . . .
C19 C 0.3495(3) 0.7435(2) 0.53605(18) 0.0465(6) Uani 1 1 d . . . . .
H19A H 0.3667 0.7986 0.4611 0.070 Uiso 1 1 calc R U . . .
H19B H 0.2528 0.7659 0.5448 0.070 Uiso 1 1 calc R U . . .
H19C H 0.3793 0.6543 0.5462 0.070 Uiso 1 1 calc R U . . .
C20 C 0.5327(2) 0.8176(2) 0.5890(2) 0.0409(6) Uani 1 1 d . . . . .
H20 H 0.5501 0.8465 0.5125 0.049 Uiso 1 1 calc R U . . .
C21 C 0.6137(2) 0.8328(2) 0.6627(2) 0.0442(6) Uani 1 1 d . . . . .
C22 C 0.7283(3) 0.8930(3) 0.6246(3) 0.0591(7) Uani 1 1 d . . . . .
H22A H 0.7348 0.9146 0.5447 0.089 Uiso 1 1 calc R U . . .
H22B H 0.8129 0.8330 0.6666 0.089 Uiso 1 1 calc R U . . .
H22C H 0.7118 0.9707 0.6379 0.089 Uiso 1 1 calc R U . . .
C23 C 0.5843(2) 0.7922(2) 0.7732(2) 0.0426(6) Uani 1 1 d . . . . .
H23 H 0.6408 0.7982 0.8259 0.051 Uiso 1 1 calc R U . . .
C24 C 0.4748(2) 0.7432(2) 0.80924(18) 0.0385(5) Uani 1 1 d . . . . .
C25 C 0.4462(3) 0.7075(3) 0.93054(19) 0.0548(7) Uani 1 1 d . . . . .
H25A H 0.3586 0.7616 0.9346 0.082 Uiso 1 1 calc R U . . .
H25B H 0.5170 0.7197 0.9704 0.082 Uiso 1 1 calc R U . . .
H25C H 0.4445 0.6179 0.9650 0.082 Uiso 1 1 calc R U . . .
C26 C 0.1480(2) 0.7319(2) 0.82414(17) 0.0351(5) Uani 1 1 d . . . . .
C27 C 0.0719(2) 0.8593(2) 0.76396(18) 0.0366(5) Uani 1 1 d . . . . .
C28 C 0.0920(3) 0.9329(2) 0.64355(18) 0.0459(6) Uani 1 1 d . . . . .
H28A H 0.0629 0.8950 0.5973 0.069 Uiso 1 1 calc R U . . .
H28B H 0.1877 0.9300 0.6363 0.069 Uiso 1 1 calc R U . . .
H28C H 0.0386 1.0218 0.6187 0.069 Uiso 1 1 calc R U . . .
C29 C -0.0282(2) 0.9191(2) 0.8124(2) 0.0463(6) Uani 1 1 d . . . . .
H29 H -0.0765 1.0054 0.7703 0.056 Uiso 1 1 calc R U . . .
C30 C -0.0598(3) 0.8562(3) 0.9206(2) 0.0523(7) Uani 1 1 d . . . . .
C31 C -0.1671(3) 0.9227(3) 0.9728(3) 0.0834(10) Uani 1 1 d . . . . .
H31A H -0.2362 0.9880 0.9145 0.125 Uiso 1 1 calc R U . . .
H31B H -0.1264 0.9629 1.0109 0.125 Uiso 1 1 calc R U . . .
H31C H -0.2087 0.8603 1.0270 0.125 Uiso 1 1 calc R U . . .
C32 C 0.0129(3) 0.7308(3) 0.9781(2) 0.0502(7) Uani 1 1 d . . . . .
H32 H -0.0077 0.6856 1.0520 0.060 Uiso 1 1 calc R U . . .
C33 C 0.1144(2) 0.6672(2) 0.93366(18) 0.0416(6) Uani 1 1 d . . . . .
C34 C 0.1883(3) 0.5313(2) 1.00839(19) 0.0563(7) Uani 1 1 d . . . . .
H34A H 0.2582 0.4978 0.9682 0.084 Uiso 1 1 calc R U . . .
H34B H 0.1244 0.4788 1.0299 0.084 Uiso 1 1 calc R U . . .
H34C H 0.2303 0.5292 1.0756 0.084 Uiso 1 1 calc R U . . .
B1 B 0.2706(3) 0.6646(2) 0.77402(19) 0.0345(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.345(3) . ?
N1 C13 1.352(3) . ?
N2 C4 1.362(3) . ?
N2 C15 1.442(3) . ?
N2 C16 1.458(3) . ?
C1 C2 1.366(3) . ?
C1 C6 1.528(3) . ?
C1 B1 1.530(3) . ?
C2 C3 1.427(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.514(3) . ?
C5 C10 1.524(3) . ?
C5 C6 1.543(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.513(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.322(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.468(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.499(3) . ?
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 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.410(3) . ?
C17 C24 1.422(3) . ?
C17 B1 1.585(3) . ?
C18 C20 1.392(3) . ?
C18 C19 1.520(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C23 1.385(3) . ?
C21 C22 1.506(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.516(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.412(3) . ?
C26 C33 1.414(3) . ?
C26 B1 1.592(3) . ?
C27 C29 1.390(3) . ?
C27 C28 1.507(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.388(3) . ?
C29 H29 0.9500 . ?
C30 C32 1.381(4) . ?
C30 C31 1.507(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.512(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C9 N1 C13 117.5(2) . . ?
C4 N2 C15 125.2(2) . . ?
C4 N2 C16 118.1(2) . . ?
C15 N2 C16 116.3(2) . . ?
C2 C1 C6 114.91(18) . . ?
C2 C1 B1 118.90(19) . . ?
C6 C1 B1 125.55(19) . . ?
C1 C2 C3 124.7(2) . . ?
C1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N2 C4 C3 123.6(2) . . ?
N2 C4 C5 119.0(2) . . ?
C3 C4 C5 117.32(19) . . ?
C4 C5 C10 112.05(17) . . ?
C4 C5 C6 110.80(18) . . ?
C10 C5 C6 109.41(17) . . ?
C4 C5 H5 108.2 . . ?
C10 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C7 C6 C1 113.94(17) . . ?
C7 C6 C5 108.21(18) . . ?
C1 C6 C5 110.82(17) . . ?
C7 C6 H6 107.9 . . ?
C1 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
N1 C9 C10 123.5(2) . . ?
N1 C9 C8 117.6(2) . . ?
C10 C9 C8 118.8(2) . . ?
C11 C10 C9 118.0(2) . . ?
C11 C10 C5 124.2(2) . . ?
C9 C10 C5 117.78(19) . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N1 C13 C12 122.1(2) . . ?
N1 C13 C14 115.8(2) . . ?
C12 C13 C14 122.2(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 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C24 117.23(19) . . ?
C18 C17 B1 120.98(19) . . ?
C24 C17 B1 121.77(19) . . ?
C20 C18 C17 120.1(2) . . ?
C20 C18 C19 117.8(2) . . ?
C17 C18 C19 122.07(19) . . ?
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 C18 122.4(2) . . ?
C21 C20 H20 118.8 . . ?
C18 C20 H20 118.8 . . ?
C23 C21 C20 117.5(2) . . ?
C23 C21 C22 120.8(2) . . ?
C20 C21 C22 121.7(2) . . ?
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 C24 122.0(2) . . ?
C21 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C17 120.6(2) . . ?
C23 C24 C25 118.3(2) . . ?
C17 C24 C25 121.1(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 . . ?
C27 C26 C33 117.1(2) . . ?
C27 C26 B1 122.04(18) . . ?
C33 C26 B1 120.9(2) . . ?
C29 C27 C26 121.1(2) . . ?
C29 C27 C28 117.7(2) . . ?
C26 C27 C28 121.2(2) . . ?
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 C27 121.9(2) . . ?
C30 C29 H29 119.1 . . ?
C27 C29 H29 119.1 . . ?
C32 C30 C29 116.8(2) . . ?
C32 C30 C31 121.8(2) . . ?
C29 C30 C31 121.4(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 C33 123.5(2) . . ?
C30 C32 H32 118.3 . . ?
C33 C32 H32 118.3 . . ?
C32 C33 C26 119.7(2) . . ?
C32 C33 C34 117.3(2) . . ?
C26 C33 C34 122.9(2) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C1 B1 C17 117.3(2) . . ?
C1 B1 C26 122.5(2) . . ?
C17 B1 C26 120.12(19) . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.157

####################################################################### 
# 
# 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_syg9a
_database_code_depnum_ccdc_archive 'CCDC 1816882'
_audit_update_record             
;
2018-01-14 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H39 B N2'
_chemical_formula_weight         486.48

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.410(5)
_cell_length_b                   34.22(2)
_cell_length_c                   10.140(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.87(2)
_cell_angle_gamma                90
_cell_volume                     2891(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5046
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.10

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28859
_diffrn_reflns_av_unetI/netI     0.1451
_diffrn_reflns_av_R_equivalents  0.1426
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         27.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6298
_reflns_number_gt                3083
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0900P)²+0.0700P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6298
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1708
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2124
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7298(3) 0.39356(8) 0.4501(3) 0.0361(7) Uani 1 1 d . . . . .
N1 N 0.8197(3) 0.26302(6) -0.0114(2) 0.0469(6) Uani 1 1 d . . . . .
N2 N 1.0796(3) 0.33477(7) 0.8339(3) 0.0637(7) Uani 1 1 d . . . . .
C1 C 0.8293(3) 0.35679(7) 0.5070(3) 0.0363(6) Uani 1 1 d . . . . .
C2 C 0.8960(3) 0.35879(7) 0.6413(3) 0.0398(7) Uani 1 1 d . . . . .
H2 H 0.8653 0.3798 0.6936 0.048 Uiso 1 1 calc R U . . .
C3 C 1.0072(3) 0.33099(7) 0.7030(3) 0.0423(7) Uani 1 1 d . . . . .
C4 C 1.0395(3) 0.29943(8) 0.6239(3) 0.0492(7) Uani 1 1 d . . . . .
H4 H 1.1120 0.2798 0.6609 0.059 Uiso 1 1 calc R U . . .
C5 C 0.9688(3) 0.29604(8) 0.4932(3) 0.0475(7) Uani 1 1 d . . . . .
H5 H 0.9917 0.2735 0.4445 0.057 Uiso 1 1 calc R U . . .
C6 C 0.8650(3) 0.32432(7) 0.4291(3) 0.0383(6) Uani 1 1 d . . . . .
C7 C 0.7965(3) 0.32031(7) 0.2896(3) 0.0426(7) Uani 1 1 d . . . . .
H7 H 0.7149 0.3386 0.2583 0.051 Uiso 1 1 calc R U . . .
C8 C 0.8330(3) 0.29450(7) 0.2001(3) 0.0451(7) Uani 1 1 d . . . . .
H8 H 0.9095 0.2750 0.2312 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7671(3) 0.29304(7) 0.0580(3) 0.0416(7) Uani 1 1 d . . . . .
C10 C 0.6608(3) 0.32040(8) -0.0046(3) 0.0554(8) Uani 1 1 d . . . . .
H10 H 0.6234 0.3411 0.0455 0.066 Uiso 1 1 calc R U . . .
C11 C 0.6093(3) 0.31766(9) -0.1396(3) 0.0601(8) Uani 1 1 d . . . . .
H11 H 0.5384 0.3367 -0.1833 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6620(3) 0.28698(8) -0.2100(3) 0.0546(8) Uani 1 1 d . . . . .
H12 H 0.6270 0.2843 -0.3026 0.066 Uiso 1 1 calc R U . . .
C13 C 0.7668(3) 0.26019(8) -0.1434(3) 0.0498(7) Uani 1 1 d . . . . .
C14 C 0.8259(4) 0.22596(9) -0.2155(3) 0.0742(10) Uani 1 1 d . . . . .
H14A H 0.7593 0.2030 -0.2039 0.111 Uiso 1 1 calc R U . . .
H14B H 0.9376 0.2204 -0.1792 0.111 Uiso 1 1 calc R U . . .
H14C H 0.8193 0.2321 -0.3105 0.111 Uiso 1 1 calc R U . . .
C15 C 1.1823(4) 0.30423(10) 0.8983(3) 0.0765(10) Uani 1 1 d . . . . .
H15A H 1.2623 0.2969 0.8411 0.115 Uiso 1 1 calc R U . . .
H15B H 1.1170 0.2814 0.9136 0.115 Uiso 1 1 calc R U . . .
H15C H 1.2369 0.3138 0.9837 0.115 Uiso 1 1 calc R U . . .
C16 C 1.0374(4) 0.36544(10) 0.9169(3) 0.0727(10) Uani 1 1 d . . . . .
H16A H 1.0640 0.3907 0.8797 0.109 Uiso 1 1 calc R U . . .
H16B H 1.0972 0.3625 1.0063 0.109 Uiso 1 1 calc R U . . .
H16C H 0.9220 0.3644 0.9221 0.109 Uiso 1 1 calc R U . . .
C17 C 0.6088(3) 0.41236(7) 0.5387(2) 0.0344(6) Uani 1 1 d . . . . .
C18 C 0.4782(3) 0.39058(7) 0.5755(2) 0.0372(6) Uani 1 1 d . . . . .
C19 C 0.4423(3) 0.34992(7) 0.5244(3) 0.0504(7) Uani 1 1 d . . . . .
H19A H 0.3817 0.3512 0.4348 0.076 Uiso 1 1 calc R U . . .
H19B H 0.3786 0.3362 0.5839 0.076 Uiso 1 1 calc R U . . .
H19C H 0.5432 0.3358 0.5211 0.076 Uiso 1 1 calc R U . . .
C20 C 0.3734(3) 0.40733(8) 0.6545(3) 0.0440(7) Uani 1 1 d . . . . .
H20 H 0.2877 0.3920 0.6787 0.053 Uiso 1 1 calc R U . . .
C21 C 0.3903(3) 0.44551(8) 0.6989(3) 0.0481(7) Uani 1 1 d . . . . .
C22 C 0.2721(4) 0.46286(10) 0.7823(3) 0.0737(10) Uani 1 1 d . . . . .
H22A H 0.1632 0.4606 0.7343 0.110 Uiso 1 1 calc R U . . .
H22B H 0.2980 0.4905 0.7998 0.110 Uiso 1 1 calc R U . . .
H22C H 0.2787 0.4487 0.8669 0.110 Uiso 1 1 calc R U . . .
C23 C 0.5174(3) 0.46647(8) 0.6621(3) 0.0480(7) Uani 1 1 d . . . . .
H23 H 0.5309 0.4928 0.6909 0.058 Uiso 1 1 calc R U . . .
C24 C 0.6268(3) 0.45097(7) 0.5849(3) 0.0395(6) Uani 1 1 d . . . . .
C25 C 0.7671(3) 0.47594(7) 0.5580(3) 0.0535(8) Uani 1 1 d . . . . .
H25A H 0.7704 0.4772 0.4619 0.080 Uiso 1 1 calc R U . . .
H25B H 0.8672 0.4645 0.6022 0.080 Uiso 1 1 calc R U . . .
H25C H 0.7547 0.5024 0.5924 0.080 Uiso 1 1 calc R U . . .
C26 C 0.7578(3) 0.41182(7) 0.3110(2) 0.0352(6) Uani 1 1 d . . . . .
C27 C 0.6286(3) 0.41991(7) 0.2079(3) 0.0420(7) Uani 1 1 d . . . . .
C28 C 0.4553(3) 0.41096(10) 0.2250(3) 0.0644(9) Uani 1 1 d . . . . .
H28A H 0.3837 0.4208 0.1478 0.097 Uiso 1 1 calc R U . . .
H28B H 0.4293 0.4236 0.3060 0.097 Uiso 1 1 calc R U . . .
H28C H 0.4414 0.3826 0.2321 0.097 Uiso 1 1 calc R U . . .
C29 C 0.6592(3) 0.43478(8) 0.0874(3) 0.0482(7) Uani 1 1 d . . . . .
H29 H 0.5715 0.4388 0.0192 0.058 Uiso 1 1 calc R U . . .
C30 C 0.8137(3) 0.44412(8) 0.0613(3) 0.0481(7) Uani 1 1 d . . . . .
C31 C 0.8414(4) 0.46194(10) -0.0701(3) 0.0725(10) Uani 1 1 d . . . . .
H31A H 0.7912 0.4455 -0.1433 0.109 Uiso 1 1 calc R U . . .
H31B H 0.9570 0.4637 -0.0739 0.109 Uiso 1 1 calc R U . . .
H31C H 0.7941 0.4881 -0.0783 0.109 Uiso 1 1 calc R U . . .
C32 C 0.9388(3) 0.43672(8) 0.1624(3) 0.0464(7) Uani 1 1 d . . . . .
H32 H 1.0450 0.4431 0.1480 0.056 Uiso 1 1 calc R U . . .
C33 C 0.9155(3) 0.42037(7) 0.2839(3) 0.0404(7) Uani 1 1 d . . . . .
C34 C 1.0629(3) 0.41336(9) 0.3857(3) 0.0561(8) Uani 1 1 d . . . . .
H34A H 1.0869 0.3853 0.3908 0.084 Uiso 1 1 calc R U . . .
H34B H 1.0423 0.4227 0.4731 0.084 Uiso 1 1 calc R U . . .
H34C H 1.1547 0.4275 0.3589 0.084 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
B1 C1 1.576(4) . ?
B1 C17 1.584(4) . ?
B1 C26 1.589(4) . ?
N1 C9 1.353(3) . ?
N1 C13 1.355(4) . ?
N2 C3 1.388(4) . ?
N2 C16 1.421(4) . ?
N2 C15 1.453(4) . ?
C1 C2 1.402(4) . ?
C1 C6 1.419(3) . ?
C2 C3 1.418(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.459(4) . ?
C7 C8 1.332(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.472(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.501(4) . ?
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 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C24 1.403(3) . ?
C17 C18 1.418(3) . ?
C18 C20 1.393(3) . ?
C18 C19 1.501(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C23 1.380(4) . ?
C21 C22 1.512(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.512(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C33 1.421(3) . ?
C26 C27 1.428(4) . ?
C27 C29 1.380(4) . ?
C27 C28 1.522(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.398(4) . ?
C29 H29 0.9500 . ?
C30 C32 1.388(4) . ?
C30 C31 1.513(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.391(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.520(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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 B1 C17 117.8(2) . . ?
C1 B1 C26 120.2(2) . . ?
C17 B1 C26 121.9(2) . . ?
C9 N1 C13 118.8(2) . . ?
C3 N2 C16 121.5(2) . . ?
C3 N2 C15 121.2(3) . . ?
C16 N2 C15 116.5(3) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 B1 116.0(2) . . ?
C6 C1 B1 124.3(2) . . ?
C1 C2 C3 123.2(2) . . ?
C1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
N2 C3 C4 121.8(2) . . ?
N2 C3 C2 122.4(2) . . ?
C4 C3 C2 115.8(3) . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 123.1(3) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C1 116.6(2) . . ?
C5 C6 C7 121.5(2) . . ?
C1 C6 C7 121.8(2) . . ?
C8 C7 C6 128.7(2) . . ?
C8 C7 H7 115.6 . . ?
C6 C7 H7 115.6 . . ?
C7 C8 C9 126.7(2) . . ?
C7 C8 H8 116.6 . . ?
C9 C8 H8 116.6 . . ?
N1 C9 C10 120.7(3) . . ?
N1 C9 C8 115.4(2) . . ?
C10 C9 C8 123.9(3) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
N1 C13 C12 122.4(3) . . ?
N1 C13 C14 116.8(3) . . ?
C12 C13 C14 120.7(3) . . ?
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 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C24 C17 C18 117.3(2) . . ?
C24 C17 B1 121.6(2) . . ?
C18 C17 B1 121.1(2) . . ?
C20 C18 C17 120.6(2) . . ?
C20 C18 C19 117.8(2) . . ?
C17 C18 C19 121.5(2) . . ?
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 C18 122.1(2) . . ?
C21 C20 H20 119.0 . . ?
C18 C20 H20 119.0 . . ?
C23 C21 C20 116.9(2) . . ?
C23 C21 C22 122.7(3) . . ?
C20 C21 C22 120.5(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 C24 123.3(2) . . ?
C21 C23 H23 118.3 . . ?
C24 C23 H23 118.3 . . ?
C23 C24 C17 119.8(2) . . ?
C23 C24 C25 118.6(2) . . ?
C17 C24 C25 121.6(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 . . ?
C33 C26 C27 117.1(2) . . ?
C33 C26 B1 120.5(2) . . ?
C27 C26 B1 122.4(2) . . ?
C29 C27 C26 120.3(2) . . ?
C29 C27 C28 118.2(2) . . ?
C26 C27 C28 121.5(2) . . ?
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 . . ?
C27 C29 C30 122.9(3) . . ?
C27 C29 H29 118.6 . . ?
C30 C29 H29 118.6 . . ?
C32 C30 C29 116.6(3) . . ?
C32 C30 C31 122.1(2) . . ?
C29 C30 C31 121.2(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 C33 122.9(2) . . ?
C30 C32 H32 118.6 . . ?
C33 C32 H32 118.6 . . ?
C32 C33 C26 120.2(2) . . ?
C32 C33 C34 117.7(2) . . ?
C26 C33 C34 122.1(2) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_sy24
_database_code_depnum_ccdc_archive 'CCDC 1590195'
_audit_update_record             
;
2017-12-09 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H36 B N S'
_chemical_formula_weight         477.49

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'
S S 0.1246 0.1234 '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                   7.9779(4)
_cell_length_b                   21.8456(11)
_cell_length_c                   15.7662(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.411(2)
_cell_angle_gamma                90
_cell_volume                     2718.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    5530
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.86

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27885
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.581
_diffrn_reflns_theta_max         27.168
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6016
_reflns_number_gt                3605
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0680P)²+0.9800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6016
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
S1 S 0.2841(6) 0.5037(2) 0.1722(3) 0.0432(7) Uani 0.5 1 d . . P A 1
S1A S 0.3667(3) 0.43400(8) 0.20955(14) 0.0526(5) Uani 0.5 1 d . . P A 2
C1 C 0.6644(3) 0.68693(10) 0.51204(14) 0.0302(5) Uani 1 1 d . . . . .
N1 N 1.0068(3) 0.57474(9) 0.67492(13) 0.0436(5) Uani 1 1 d . . . . .
B1 B 0.5447(3) 0.73340(11) 0.45907(16) 0.0309(6) Uani 1 1 d . . . . .
C2 C 0.6904(3) 0.62433(10) 0.49197(14) 0.0291(5) Uani 1 1 d . . . . .
C6 C 0.7560(3) 0.70742(10) 0.59009(15) 0.0360(6) Uani 1 1 d . . . . .
H6A H 0.7427 0.7485 0.6055 0.043 Uiso 1 1 calc R U . . .
C5 C 0.8629(3) 0.67156(10) 0.64495(15) 0.0367(6) Uani 1 1 d . . . . .
H5A H 0.9166 0.6878 0.6971 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8924(3) 0.61056(10) 0.62348(14) 0.0328(5) Uani 1 1 d . . . . .
C3 C 0.8033(3) 0.58861(10) 0.54637(15) 0.0325(5) Uani 1 1 d . . . . .
H3A H 0.8207 0.5478 0.5307 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6034(3) 0.59730(10) 0.41206(15) 0.0325(5) Uani 1 1 d . . . . .
H7A H 0.5694 0.6244 0.3665 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4779(3) 0.51308(10) 0.31845(14) 0.0334(5) Uani 1 1 d . . . . .
C8 C 0.5680(3) 0.53847(10) 0.39787(15) 0.0355(5) Uani 1 1 d . . . . .
H8A H 0.6039 0.5109 0.4427 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3815(4) 0.54626(13) 0.25331(18) 0.0487(7) Uani 1 1 d . . . . .
H10A H 0.361(3) 0.5875(12) 0.2519(16) 0.050 Uiso 1 1 d . U . . .
C11 C 0.4726(4) 0.45109(12) 0.2978(2) 0.0522(7) Uani 1 1 d . . . . .
H11A H 0.521(3) 0.4213(12) 0.3339(17) 0.050 Uiso 1 1 d . U . . .
C12 C 0.367(3) 0.4381(12) 0.2083(14) 0.214(9) Uani 0.5 1 d . . P A 1
H12B H 0.3525 0.4001 0.1803 0.257 Uiso 0.5 1 calc R U P A 1
C12A C 0.320(2) 0.5071(10) 0.1843(13) 0.064(6) Uani 0.5 1 d . . P A 2
H12A H 0.2617 0.5203 0.1314 0.077 Uiso 0.5 1 calc R U P A 2
C13 C 1.0195(4) 0.51023(12) 0.65821(19) 0.0539(7) Uani 1 1 d . . . . .
H13A H 1.0524 0.5043 0.6019 0.081 Uiso 1 1 calc R U . . .
H13B H 0.9107 0.4909 0.6601 0.081 Uiso 1 1 calc R U . . .
H13C H 1.1041 0.4920 0.7013 0.081 Uiso 1 1 calc R U . . .
C14 C 1.0954(3) 0.59815(13) 0.75467(18) 0.0553(8) Uani 1 1 d . . . . .
H14A H 1.1412 0.6383 0.7452 0.083 Uiso 1 1 calc R U . . .
H14B H 1.1870 0.5706 0.7762 0.083 Uiso 1 1 calc R U . . .
H14C H 1.0173 0.6013 0.7962 0.083 Uiso 1 1 calc R U . . .
C15 C 0.5987(3) 0.80304(10) 0.47397(14) 0.0309(5) Uani 1 1 d . . . . .
C16 C 0.4973(3) 0.84458(11) 0.51188(16) 0.0385(6) Uani 1 1 d . . . . .
C17 C 0.3204(4) 0.82825(14) 0.5277(2) 0.0694(10) Uani 1 1 d . . . . .
H17A H 0.2704 0.8630 0.5531 0.104 Uiso 1 1 calc R U . . .
H17B H 0.3255 0.7936 0.5664 0.104 Uiso 1 1 calc R U . . .
H17C H 0.2516 0.8177 0.4737 0.104 Uiso 1 1 calc R U . . .
C18 C 0.5614(3) 0.90182(11) 0.53865(16) 0.0430(6) Uani 1 1 d . . . . .
H18A H 0.4925 0.9285 0.5651 0.052 Uiso 1 1 calc R U . . .
C19 C 0.7214(3) 0.92084(10) 0.52798(15) 0.0384(6) Uani 1 1 d . . . . .
C20 C 0.7896(4) 0.98198(12) 0.5625(2) 0.0581(8) Uani 1 1 d . . . . .
H20A H 0.7021 1.0037 0.5870 0.087 Uiso 1 1 calc R U . . .
H20B H 0.8240 1.0060 0.5163 0.087 Uiso 1 1 calc R U . . .
H20C H 0.8865 0.9754 0.6064 0.087 Uiso 1 1 calc R U . . .
C21 C 0.8177(3) 0.88100(10) 0.48689(15) 0.0376(6) Uani 1 1 d . . . . .
H21A H 0.9256 0.8935 0.4765 0.045 Uiso 1 1 calc R U . . .
C23 C 0.7602(3) 0.82312(10) 0.46043(14) 0.0329(5) Uani 1 1 d . . . . .
C24 C 0.3759(3) 0.71329(9) 0.39943(14) 0.0296(5) Uani 1 1 d . . . . .
C25 C 0.2543(3) 0.67535(10) 0.43068(14) 0.0326(5) Uani 1 1 d . . . . .
C26 C 0.2728(3) 0.65395(13) 0.52258(16) 0.0492(7) Uani 1 1 d . . . . .
H26A H 0.1666 0.6599 0.5445 0.074 Uiso 1 1 calc R U . . .
H26B H 0.3614 0.6773 0.5569 0.074 Uiso 1 1 calc R U . . .
H26C H 0.3024 0.6109 0.5254 0.074 Uiso 1 1 calc R U . . .
C27 C 0.1093(3) 0.65713(10) 0.37703(15) 0.0358(5) Uani 1 1 d . . . . .
H27A H 0.0304 0.6321 0.3994 0.043 Uiso 1 1 calc R U . . .
C28 C 0.0768(3) 0.67438(10) 0.29198(16) 0.0388(6) Uani 1 1 d . . . . .
C29 C -0.0807(4) 0.65346(14) 0.2350(2) 0.0639(9) Uani 1 1 d . . . . .
H29A H -0.0614 0.6543 0.1756 0.096 Uiso 1 1 calc R U . . .
H29B H -0.1740 0.6805 0.2421 0.096 Uiso 1 1 calc R U . . .
H29C H -0.1082 0.6121 0.2503 0.096 Uiso 1 1 calc R U . . .
C30 C 0.1945(3) 0.71200(11) 0.26118(15) 0.0397(6) Uani 1 1 d . . . . .
H30A H 0.1745 0.7246 0.2036 0.048 Uiso 1 1 calc R U . . .
C31 C 0.3413(3) 0.73164(10) 0.31291(15) 0.0342(5) Uani 1 1 d . . . . .
C32 C 0.4638(3) 0.77073(13) 0.27245(17) 0.0541(7) Uani 1 1 d . . . . .
H32A H 0.4098 0.7848 0.2167 0.081 Uiso 1 1 calc R U . . .
H32B H 0.5634 0.7468 0.2657 0.081 Uiso 1 1 calc R U . . .
H32C H 0.4969 0.8058 0.3089 0.081 Uiso 1 1 calc R U . . .
C22 C 0.8752(3) 0.78310(12) 0.41638(19) 0.0498(7) Uani 1 1 d . . . . .
H22A H 0.9376 0.8083 0.3811 0.075 Uiso 1 1 calc R U . . .
H22B H 0.8079 0.7533 0.3806 0.075 Uiso 1 1 calc R U . . .
H22C H 0.9543 0.7620 0.4591 0.075 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
S1 C12 1.64(3) . ?
S1 C10 1.676(5) . ?
S1A C11 1.564(4) . ?
S1A C12A 1.67(2) . ?
C1 C6 1.409(3) . ?
C1 C2 1.426(3) . ?
C1 B1 1.552(3) . ?
N1 C4 1.373(3) . ?
N1 C13 1.440(3) . ?
N1 C14 1.443(3) . ?
B1 C24 1.587(3) . ?
B1 C15 1.589(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.470(3) . ?
C6 C5 1.369(3) . ?
C6 H6A 0.9400 . ?
C5 C4 1.403(3) . ?
C5 H5A 0.9400 . ?
C4 C3 1.400(3) . ?
C3 H3A 0.9400 . ?
C7 C8 1.328(3) . ?
C7 H7A 0.9400 . ?
C9 C11 1.392(3) . ?
C9 C10 1.393(3) . ?
C9 C8 1.459(3) . ?
C8 H8A 0.9400 . ?
C10 C12A 1.413(18) . ?
C10 H10A 0.92(3) . ?
C11 C12 1.56(2) . ?
C11 H11A 0.91(3) . ?
C12 H12B 0.9400 . ?
C12A H12A 0.9400 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.406(3) . ?
C15 C23 1.406(3) . ?
C16 C18 1.393(3) . ?
C16 C17 1.511(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 C19 1.376(3) . ?
C18 H18A 0.9400 . ?
C19 C21 1.383(3) . ?
C19 C20 1.514(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C23 1.388(3) . ?
C21 H21A 0.9400 . ?
C23 C22 1.508(3) . ?
C24 C31 1.410(3) . ?
C24 C25 1.418(3) . ?
C25 C27 1.388(3) . ?
C25 C26 1.509(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 C28 1.380(3) . ?
C27 H27A 0.9400 . ?
C28 C30 1.388(3) . ?
C28 C29 1.506(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C30 C31 1.393(3) . ?
C30 H30A 0.9400 . ?
C31 C32 1.508(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C10 95.9(8) . . ?
C11 S1A C12A 93.2(6) . . ?
C6 C1 C2 115.15(19) . . ?
C6 C1 B1 117.5(2) . . ?
C2 C1 B1 127.3(2) . . ?
C4 N1 C13 120.5(2) . . ?
C4 N1 C14 120.7(2) . . ?
C13 N1 C14 117.9(2) . . ?
C1 B1 C24 122.7(2) . . ?
C1 B1 C15 114.47(19) . . ?
C24 B1 C15 122.73(19) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 C7 119.1(2) . . ?
C1 C2 C7 120.64(19) . . ?
C5 C6 C1 124.4(2) . . ?
C5 C6 H6A 117.8 . . ?
C1 C6 H6A 117.8 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
N1 C4 C3 121.8(2) . . ?
N1 C4 C5 121.3(2) . . ?
C3 C4 C5 116.9(2) . . ?
C2 C3 C4 123.0(2) . . ?
C2 C3 H3A 118.5 . . ?
C4 C3 H3A 118.5 . . ?
C8 C7 C2 126.5(2) . . ?
C8 C7 H7A 116.7 . . ?
C2 C7 H7A 116.7 . . ?
C11 C9 C10 109.8(2) . . ?
C11 C9 C8 124.4(2) . . ?
C10 C9 C8 125.8(2) . . ?
C7 C8 C9 125.3(2) . . ?
C7 C8 H8A 117.3 . . ?
C9 C8 H8A 117.3 . . ?
C9 C10 C12A 110.1(9) . . ?
C9 C10 S1 114.7(3) . . ?
C9 C10 H10A 127.4(16) . . ?
C12A C10 H10A 122.5(19) . . ?
S1 C10 H10A 117.8(16) . . ?
C9 C11 C12 112.4(10) . . ?
C9 C11 S1A 115.7(2) . . ?
C9 C11 H11A 123.6(17) . . ?
C12 C11 H11A 123.9(19) . . ?
S1A C11 H11A 120.6(17) . . ?
C11 C12 S1 106.9(14) . . ?
C11 C12 H12B 126.6 . . ?
S1 C12 H12B 126.6 . . ?
C10 C12A S1A 110.8(13) . . ?
C10 C12A H12A 124.6 . . ?
S1A C12A H12A 124.6 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C23 117.4(2) . . ?
C16 C15 B1 121.3(2) . . ?
C23 C15 B1 120.72(19) . . ?
C18 C16 C15 120.0(2) . . ?
C18 C16 C17 118.2(2) . . ?
C15 C16 C17 121.8(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 C16 122.7(2) . . ?
C19 C18 H18A 118.7 . . ?
C16 C18 H18A 118.7 . . ?
C18 C19 C21 117.2(2) . . ?
C18 C19 C20 120.9(2) . . ?
C21 C19 C20 121.9(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 . . ?
C19 C21 C23 122.1(2) . . ?
C19 C21 H21A 118.9 . . ?
C23 C21 H21A 118.9 . . ?
C21 C23 C15 120.6(2) . . ?
C21 C23 C22 118.0(2) . . ?
C15 C23 C22 121.5(2) . . ?
C31 C24 C25 117.07(19) . . ?
C31 C24 B1 121.6(2) . . ?
C25 C24 B1 121.33(19) . . ?
C27 C25 C24 120.5(2) . . ?
C27 C25 C26 116.9(2) . . ?
C24 C25 C26 122.6(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C25 122.4(2) . . ?
C28 C27 H27A 118.8 . . ?
C25 C27 H27A 118.8 . . ?
C27 C28 C30 117.5(2) . . ?
C27 C28 C29 121.3(2) . . ?
C30 C28 C29 121.3(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 C31 122.1(2) . . ?
C28 C30 H30A 119.0 . . ?
C31 C30 H30A 119.0 . . ?
C30 C31 C24 120.5(2) . . ?
C30 C31 C32 117.9(2) . . ?
C24 C31 C32 121.5(2) . . ?
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 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_sy25
_database_code_depnum_ccdc_archive 'CCDC 1590111'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H40 B N O'
_chemical_formula_weight         501.49

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      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                   7.2959(3)
_cell_length_b                   22.3592(8)
_cell_length_c                   17.9840(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.626(2)
_cell_angle_gamma                90
_cell_volume                     2930.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6333
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.07

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35189
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         27.238
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6531
_reflns_number_gt                4403
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0650P)²+1.3000P] 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         6531
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1614
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.023
_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
B1 B 0.6237(3) 0.27850(9) 0.43057(12) 0.0238(5) Uani 1 1 d . . . . .
O1 O 0.8384(2) 0.58496(6) 0.38598(8) 0.0354(4) Uani 1 1 d . . . . .
N1 N 0.6377(2) 0.43905(7) 0.68153(9) 0.0316(4) Uani 1 1 d . . . . .
C1 C 0.6478(3) 0.32329(8) 0.49542(10) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.6035(3) 0.30373(8) 0.56682(10) 0.0247(4) Uani 1 1 d . . . . .
H2 H 0.5757 0.2626 0.5731 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5980(3) 0.34040(8) 0.62800(10) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.5649 0.3245 0.6745 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6414(3) 0.40154(8) 0.62191(10) 0.0230(4) Uani 1 1 d . . . . .
C5 C 0.6933(3) 0.42193(8) 0.55200(10) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.7286 0.4626 0.5470 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6951(2) 0.38507(8) 0.48999(10) 0.0216(4) Uani 1 1 d . . . . .
C7 C 0.7555(3) 0.41018(8) 0.41930(10) 0.0239(4) Uani 1 1 d . . . . .
H7 H 0.8024 0.3829 0.3845 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7503(3) 0.46773(8) 0.39988(10) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.7072 0.4954 0.4351 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8060(3) 0.49157(8) 0.32840(11) 0.0258(4) Uani 1 1 d . . . . .
C10 C 0.8124(3) 0.45651(9) 0.26469(11) 0.0338(5) Uani 1 1 d . . . . .
H10 H 0.7784 0.4156 0.2670 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8675(3) 0.48004(10) 0.19786(12) 0.0418(6) Uani 1 1 d . . . . .
H11 H 0.8711 0.4554 0.1549 0.050 Uiso 1 1 calc R U . . .
C12 C 0.9170(3) 0.53964(10) 0.19413(13) 0.0406(5) Uani 1 1 d . . . . .
H12 H 0.9568 0.5557 0.1487 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9090(3) 0.57587(9) 0.25585(12) 0.0333(5) Uani 1 1 d . . . . .
H13 H 0.9424 0.6168 0.2527 0.040 Uiso 1 1 calc R U . . .
C14 C 0.8522(3) 0.55262(8) 0.32263(11) 0.0268(4) Uani 1 1 d . . . . .
C15 C 0.8806(3) 0.64724(9) 0.38432(15) 0.0426(6) Uani 1 1 d . . . . .
H15A H 1.0095 0.6526 0.3726 0.064 Uiso 1 1 calc R U . . .
H15B H 0.8597 0.6650 0.4330 0.064 Uiso 1 1 calc R U . . .
H15C H 0.8018 0.6670 0.3462 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5981(3) 0.41721(10) 0.75508(11) 0.0362(5) Uani 1 1 d . . . . .
H16A H 0.4755 0.3992 0.7536 0.054 Uiso 1 1 calc R U . . .
H16B H 0.6027 0.4506 0.7905 0.054 Uiso 1 1 calc R U . . .
H16C H 0.6894 0.3871 0.7708 0.054 Uiso 1 1 calc R U . . .
C17 C 0.6843(3) 0.50193(9) 0.67548(12) 0.0346(5) Uani 1 1 d . . . . .
H17A H 0.8158 0.5059 0.6679 0.052 Uiso 1 1 calc R U . . .
H17B H 0.6540 0.5227 0.7213 0.052 Uiso 1 1 calc R U . . .
H17C H 0.6143 0.5196 0.6331 0.052 Uiso 1 1 calc R U . . .
C18 C 0.6466(3) 0.20861(8) 0.44559(10) 0.0243(4) Uani 1 1 d . . . . .
C19 C 0.8084(3) 0.18551(8) 0.48137(11) 0.0281(4) Uani 1 1 d . . . . .
C20 C 0.9607(3) 0.22543(9) 0.51250(13) 0.0370(5) Uani 1 1 d . . . . .
H20A H 1.0760 0.2029 0.5157 0.056 Uiso 1 1 calc R U . . .
H20B H 0.9309 0.2392 0.5623 0.056 Uiso 1 1 calc R U . . .
H20C H 0.9737 0.2600 0.4797 0.056 Uiso 1 1 calc R U . . .
C21 C 0.8344(3) 0.12386(9) 0.48822(11) 0.0321(5) Uani 1 1 d . . . . .
H21 H 0.9458 0.1093 0.5110 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7025(3) 0.08323(8) 0.46275(11) 0.0313(5) Uani 1 1 d . . . . .
C23 C 0.7362(4) 0.01664(9) 0.46854(14) 0.0449(6) Uani 1 1 d . . . . .
H23A H 0.6246 -0.0049 0.4522 0.067 Uiso 1 1 calc R U . . .
H23B H 0.7694 0.0062 0.5203 0.067 Uiso 1 1 calc R U . . .
H23C H 0.8366 0.0055 0.4369 0.067 Uiso 1 1 calc R U . . .
C24 C 0.5416(3) 0.10566(8) 0.43048(11) 0.0290(5) Uani 1 1 d . . . . .
H24 H 0.4476 0.0785 0.4146 0.035 Uiso 1 1 calc R U . . .
C25 C 0.5119(3) 0.16697(8) 0.42036(10) 0.0263(4) Uani 1 1 d . . . . .
C26 C 0.3337(3) 0.18603(9) 0.38195(13) 0.0380(5) Uani 1 1 d . . . . .
H26A H 0.3549 0.1966 0.3301 0.057 Uiso 1 1 calc R U . . .
H26B H 0.2849 0.2208 0.4076 0.057 Uiso 1 1 calc R U . . .
H26C H 0.2452 0.1531 0.3831 0.057 Uiso 1 1 calc R U . . .
C27 C 0.5665(3) 0.30003(8) 0.34870(10) 0.0244(4) Uani 1 1 d . . . . .
C28 C 0.6746(3) 0.28665(8) 0.28772(11) 0.0281(4) Uani 1 1 d . . . . .
C29 C 0.8546(3) 0.25366(10) 0.29805(12) 0.0385(5) Uani 1 1 d . . . . .
H29A H 0.9146 0.2518 0.2504 0.058 Uiso 1 1 calc R U . . .
H29B H 0.8318 0.2130 0.3157 0.058 Uiso 1 1 calc R U . . .
H29C H 0.9342 0.2747 0.3347 0.058 Uiso 1 1 calc R U . . .
C30 C 0.6215(3) 0.30672(8) 0.21650(11) 0.0330(5) Uani 1 1 d . . . . .
H30 H 0.6985 0.2987 0.1765 0.040 Uiso 1 1 calc R U . . .
C31 C 0.4602(3) 0.33785(9) 0.20252(11) 0.0365(5) Uani 1 1 d . . . . .
C32 C 0.4059(4) 0.35968(12) 0.12498(13) 0.0596(8) Uani 1 1 d . . . . .
H32A H 0.3659 0.3257 0.0939 0.089 Uiso 1 1 calc R U . . .
H32B H 0.5114 0.3790 0.1032 0.089 Uiso 1 1 calc R U . . .
H32C H 0.3052 0.3885 0.1276 0.089 Uiso 1 1 calc R U . . .
C33 C 0.3523(3) 0.34988(8) 0.26215(12) 0.0339(5) Uani 1 1 d . . . . .
H33 H 0.2393 0.3703 0.2533 0.041 Uiso 1 1 calc R U . . .
C34 C 0.4040(3) 0.33304(8) 0.33476(11) 0.0283(4) Uani 1 1 d . . . . .
C35 C 0.2803(3) 0.35056(9) 0.39644(12) 0.0356(5) Uani 1 1 d . . . . .
H35A H 0.1650 0.3667 0.3747 0.053 Uiso 1 1 calc R U . . .
H35B H 0.3414 0.3810 0.4280 0.053 Uiso 1 1 calc R U . . .
H35C H 0.2543 0.3153 0.4265 0.053 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
B1 C1 1.541(3) . ?
B1 C27 1.587(3) . ?
B1 C18 1.594(3) . ?
O1 C14 1.357(2) . ?
O1 C15 1.427(2) . ?
N1 C4 1.362(2) . ?
N1 C16 1.451(3) . ?
N1 C17 1.451(2) . ?
C1 C2 1.408(3) . ?
C1 C6 1.428(2) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(3) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.475(3) . ?
C7 C8 1.334(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.466(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C9 C14 1.411(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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 C25 1.413(3) . ?
C18 C19 1.416(3) . ?
C19 C21 1.396(3) . ?
C19 C20 1.512(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 C24 1.380(3) . ?
C22 C23 1.512(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.399(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.506(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C34 1.410(3) . ?
C27 C28 1.412(3) . ?
C28 C30 1.395(3) . ?
C28 C29 1.510(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.380(3) . ?
C30 H30 0.9500 . ?
C31 C33 1.385(3) . ?
C31 C32 1.513(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.394(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.513(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 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 B1 C27 121.42(16) . . ?
C1 B1 C18 120.10(17) . . ?
C27 B1 C18 118.41(16) . . ?
C14 O1 C15 118.56(17) . . ?
C4 N1 C16 121.47(16) . . ?
C4 N1 C17 121.60(16) . . ?
C16 N1 C17 116.82(16) . . ?
C2 C1 C6 115.40(16) . . ?
C2 C1 B1 117.73(16) . . ?
C6 C1 B1 126.61(16) . . ?
C3 C2 C1 124.14(17) . . ?
C3 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C2 C3 C4 120.13(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
N1 C4 C5 121.34(17) . . ?
N1 C4 C3 121.58(17) . . ?
C5 C4 C3 117.07(17) . . ?
C6 C5 C4 122.63(17) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 120.56(16) . . ?
C5 C6 C7 118.75(16) . . ?
C1 C6 C7 120.63(16) . . ?
C8 C7 C6 125.93(17) . . ?
C8 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
C7 C8 C9 125.09(18) . . ?
C7 C8 H8 117.5 . . ?
C9 C8 H8 117.5 . . ?
C10 C9 C14 117.87(18) . . ?
C10 C9 C8 122.59(17) . . ?
C14 C9 C8 119.53(17) . . ?
C11 C10 C9 121.44(19) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.12(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O1 C14 C13 124.26(18) . . ?
O1 C14 C9 115.24(17) . . ?
C13 C14 C9 120.49(19) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C25 C18 C19 117.29(16) . . ?
C25 C18 B1 121.71(17) . . ?
C19 C18 B1 120.91(17) . . ?
C21 C19 C18 120.51(18) . . ?
C21 C19 C20 117.08(18) . . ?
C18 C19 C20 122.41(17) . . ?
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 C19 121.88(19) . . ?
C22 C21 H21 119.1 . . ?
C19 C21 H21 119.1 . . ?
C24 C22 C21 117.73(17) . . ?
C24 C22 C23 121.3(2) . . ?
C21 C22 C23 120.9(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 C25 122.31(19) . . ?
C22 C24 H24 118.8 . . ?
C25 C24 H24 118.8 . . ?
C24 C25 C18 120.19(18) . . ?
C24 C25 C26 117.53(17) . . ?
C18 C25 C26 122.28(17) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C34 C27 C28 117.90(17) . . ?
C34 C27 B1 120.47(17) . . ?
C28 C27 B1 121.63(17) . . ?
C30 C28 C27 120.25(19) . . ?
C30 C28 C29 118.24(19) . . ?
C27 C28 C29 121.42(17) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C28 121.9(2) . . ?
C31 C30 H30 119.1 . . ?
C28 C30 H30 119.1 . . ?
C30 C31 C33 117.81(19) . . ?
C30 C31 C32 121.0(2) . . ?
C33 C31 C32 121.1(2) . . ?
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 C34 122.3(2) . . ?
C31 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
C33 C34 C27 119.81(19) . . ?
C33 C34 C35 118.16(19) . . ?
C27 C34 C35 122.03(18) . . ?
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 . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_sy12
_database_code_depnum_ccdc_archive 'CCDC 1590110'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H43 B N2'
_chemical_formula_weight         550.56

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                   8.1029(4)
_cell_length_b                   11.3778(6)
_cell_length_c                   18.5298(11)
_cell_angle_alpha                87.821(2)
_cell_angle_beta                 85.222(2)
_cell_angle_gamma                71.032(2)
_cell_volume                     1609.84(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7402
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.02

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37385
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.202
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7672
_reflns_number_gt                4744
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0700P)²+0.3000P] 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         7672
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.010
_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 N 0.2893(2) 0.63991(15) 0.50348(9) 0.0356(4) Uani 1 1 d . . . . .
N2 N 0.0742(2) 0.10095(15) 0.61231(10) 0.0397(4) Uani 1 1 d . . . . .
C1 C 0.2829(2) 0.52622(16) 0.72373(9) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.3218(2) 0.63336(16) 0.69945(10) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.3461 0.6829 0.7346 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3271(2) 0.67124(17) 0.62822(10) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.3583 0.7433 0.6153 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2863(2) 0.60334(16) 0.57463(10) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.3318(3) 0.7503(2) 0.48118(12) 0.0442(6) Uani 1 1 d . . . . .
H5A H 0.4503 0.7413 0.4938 0.066 Uiso 1 1 calc R U . . .
H5B H 0.2481 0.8226 0.5059 0.066 Uiso 1 1 calc R U . . .
H5C H 0.3257 0.7620 0.4287 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2469(3) 0.5693(2) 0.44837(11) 0.0390(5) Uani 1 1 d . . . . .
H6A H 0.2558 0.6087 0.4009 0.059 Uiso 1 1 calc R U . . .
H6B H 0.1273 0.5674 0.4591 0.059 Uiso 1 1 calc R U . . .
H6C H 0.3290 0.4842 0.4479 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2385(2) 0.49909(16) 0.59752(10) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.2057 0.4537 0.5625 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2372(2) 0.45966(15) 0.66936(10) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.1802(2) 0.35165(16) 0.68958(10) 0.0254(4) Uani 1 1 d . . . . .
H9 H 0.1436 0.3443 0.7391 0.030 Uiso 1 1 calc R U . . .
C10 C 0.1746(2) 0.26363(17) 0.64587(11) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.2110 0.2704 0.5962 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1175(2) 0.15702(16) 0.66719(11) 0.0281(4) Uani 1 1 d . . . . .
C12 C 0.1097(2) 0.11439(18) 0.73824(12) 0.0352(5) Uani 1 1 d . . . . .
H12 H 0.1419 0.1549 0.7760 0.042 Uiso 1 1 calc R U . . .
C13 C 0.0547(3) 0.0124(2) 0.75358(14) 0.0446(6) Uani 1 1 d . . . . .
H13 H 0.0495 -0.0185 0.8018 0.054 Uiso 1 1 calc R U . . .
C14 C 0.0076(3) -0.04339(19) 0.69744(15) 0.0472(6) Uani 1 1 d . . . . .
H14 H -0.0328 -0.1126 0.7062 0.057 Uiso 1 1 calc R U . . .
C15 C 0.0205(3) 0.0035(2) 0.62895(14) 0.0482(6) Uani 1 1 d . . . . .
H15 H -0.0110 -0.0360 0.5906 0.058 Uiso 1 1 calc R U . . .
C16 C 0.3664(2) 0.34424(16) 0.82882(9) 0.0224(4) Uani 1 1 d . . . . .
C17 C 0.2731(2) 0.30321(16) 0.88672(10) 0.0254(4) Uani 1 1 d . . . . .
C18 C 0.1197(3) 0.39182(19) 0.92933(12) 0.0424(6) Uani 1 1 d . . . . .
H18A H 0.0314 0.4372 0.8963 0.064 Uiso 1 1 calc R U . . .
H18B H 0.1592 0.4509 0.9545 0.064 Uiso 1 1 calc R U . . .
H18C H 0.0686 0.3451 0.9649 0.064 Uiso 1 1 calc R U . . .
C19 C 0.3166(2) 0.17733(17) 0.90398(10) 0.0286(4) Uani 1 1 d . . . . .
H19 H 0.2501 0.1517 0.9423 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4538(2) 0.08764(17) 0.86724(10) 0.0296(4) Uani 1 1 d . . . . .
C21 C 0.4965(3) -0.04805(18) 0.88690(13) 0.0481(6) Uani 1 1 d . . . . .
H21A H 0.3975 -0.0757 0.8780 0.072 Uiso 1 1 calc R U . . .
H21B H 0.5193 -0.0603 0.9382 0.072 Uiso 1 1 calc R U . . .
H21C H 0.6006 -0.0965 0.8573 0.072 Uiso 1 1 calc R U . . .
C22 C 0.5484(2) 0.12845(17) 0.81214(10) 0.0287(4) Uani 1 1 d . . . . .
H22 H 0.6443 0.0690 0.7869 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5085(2) 0.25322(17) 0.79222(10) 0.0259(4) Uani 1 1 d . . . . .
C24 C 0.6249(3) 0.2856(2) 0.73249(11) 0.0407(5) Uani 1 1 d . . . . .
H24A H 0.5586 0.3148 0.6898 0.061 Uiso 1 1 calc R U . . .
H24B H 0.7253 0.2118 0.7200 0.061 Uiso 1 1 calc R U . . .
H24C H 0.6664 0.3513 0.7488 0.061 Uiso 1 1 calc R U . . .
C25 C 0.2885(2) 0.59062(16) 0.86131(9) 0.0231(4) Uani 1 1 d . . . . .
C26 C 0.1249(2) 0.68282(16) 0.87603(10) 0.0246(4) Uani 1 1 d . . . . .
C27 C -0.0337(2) 0.68966(19) 0.83635(11) 0.0356(5) Uani 1 1 d . . . . .
H27A H -0.0017 0.6236 0.8003 0.053 Uiso 1 1 calc R U . . .
H27B H -0.0761 0.7707 0.8120 0.053 Uiso 1 1 calc R U . . .
H27C H -0.1261 0.6791 0.8710 0.053 Uiso 1 1 calc R U . . .
C28 C 0.1020(3) 0.76729(17) 0.93112(10) 0.0296(4) Uani 1 1 d . . . . .
H28 H -0.0095 0.8282 0.9405 0.035 Uiso 1 1 calc R U . . .
C29 C 0.2369(3) 0.76551(18) 0.97285(10) 0.0334(5) Uani 1 1 d . . . . .
C30 C 0.2056(3) 0.8532(2) 1.03543(13) 0.0523(6) Uani 1 1 d . . . . .
H30A H 0.1766 0.9388 1.0170 0.078 Uiso 1 1 calc R U . . .
H30B H 0.3116 0.8325 1.0618 0.078 Uiso 1 1 calc R U . . .
H30C H 0.1084 0.8451 1.0682 0.078 Uiso 1 1 calc R U . . .
C31 C 0.4281(2) 0.59251(17) 0.90152(10) 0.0262(4) Uani 1 1 d . . . . .
C32 C 0.3997(3) 0.67867(18) 0.95608(10) 0.0324(5) Uani 1 1 d . . . . .
H32 H 0.4951 0.6781 0.9828 0.039 Uiso 1 1 calc R U . . .
C33 C 0.6109(2) 0.50405(19) 0.88443(12) 0.0371(5) Uani 1 1 d . . . . .
H33A H 0.6083 0.4185 0.8858 0.056 Uiso 1 1 calc R U . . .
H33B H 0.6879 0.5132 0.9203 0.056 Uiso 1 1 calc R U . . .
H33C H 0.6549 0.5231 0.8360 0.056 Uiso 1 1 calc R U . . .
C34 C 0.1885(3) 0.2304(3) 0.42387(15) 0.0554(7) Uani 1 1 d . . . . .
H34 H 0.0974 0.2726 0.4585 0.067 Uiso 1 1 calc R U . . .
C35 C 0.3020(3) 0.1161(3) 0.44024(14) 0.0544(7) Uani 1 1 d . . . . .
H35 H 0.2907 0.0791 0.4864 0.065 Uiso 1 1 calc R U . . .
C36 C 0.4325(3) 0.0548(2) 0.38970(15) 0.0531(6) Uani 1 1 d . . . . .
H36 H 0.5105 -0.0251 0.4009 0.064 Uiso 1 1 calc R U . . .
C37 C 0.4508(3) 0.1081(2) 0.32324(14) 0.0492(6) Uani 1 1 d . . . . .
H37 H 0.5419 0.0657 0.2886 0.059 Uiso 1 1 calc R U . . .
C38 C 0.3368(3) 0.2234(2) 0.30691(14) 0.0476(6) Uani 1 1 d . . . . .
H38 H 0.3484 0.2607 0.2608 0.057 Uiso 1 1 calc R U . . .
C39 C 0.2060(3) 0.2844(2) 0.35749(15) 0.0546(7) Uani 1 1 d . . . . .
H39 H 0.1275 0.3642 0.3464 0.066 Uiso 1 1 calc R U . . .
B1 B 0.3112(2) 0.48590(19) 0.80397(11) 0.0225(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.368(2) . ?
N1 C5 1.444(3) . ?
N1 C6 1.451(3) . ?
N2 C15 1.334(3) . ?
N2 C11 1.349(2) . ?
C1 C2 1.405(2) . ?
C1 C8 1.424(2) . ?
C1 B1 1.553(3) . ?
C2 C3 1.374(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(3) . ?
C3 H3 0.9500 . ?
C4 C7 1.403(2) . ?
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 C8 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.473(2) . ?
C9 C10 1.326(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.463(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.413(2) . ?
C16 C23 1.416(2) . ?
C16 B1 1.587(3) . ?
C17 C19 1.390(2) . ?
C17 C18 1.506(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 C22 1.382(3) . ?
C20 C21 1.506(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.392(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.507(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.410(2) . ?
C25 C31 1.412(2) . ?
C25 B1 1.582(3) . ?
C26 C28 1.388(3) . ?
C26 C27 1.512(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.385(3) . ?
C28 H28 0.9500 . ?
C29 C32 1.386(3) . ?
C29 C30 1.509(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.388(3) . ?
C31 C33 1.511(3) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.367(4) . ?
C34 C39 1.371(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.373(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.370(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.377(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.374(3) . ?
C38 H38 0.9500 . ?
C39 H39 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
C4 N1 C5 121.23(16) . . ?
C4 N1 C6 120.60(16) . . ?
C5 N1 C6 118.16(16) . . ?
C15 N2 C11 117.35(19) . . ?
C2 C1 C8 115.38(16) . . ?
C2 C1 B1 117.43(16) . . ?
C8 C1 B1 126.89(15) . . ?
C3 C2 C1 124.35(17) . . ?
C3 C2 H2 117.8 . . ?
C1 C2 H2 117.8 . . ?
C2 C3 C4 119.90(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N1 C4 C7 121.90(16) . . ?
N1 C4 C3 120.90(16) . . ?
C7 C4 C3 117.19(16) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 122.63(17) . . ?
C8 C7 H7 118.7 . . ?
C4 C7 H7 118.7 . . ?
C7 C8 C1 120.45(16) . . ?
C7 C8 C9 119.48(16) . . ?
C1 C8 C9 120.02(16) . . ?
C10 C9 C8 126.80(17) . . ?
C10 C9 H9 116.6 . . ?
C8 C9 H9 116.6 . . ?
C9 C10 C11 125.86(18) . . ?
C9 C10 H10 117.1 . . ?
C11 C10 H10 117.1 . . ?
N2 C11 C12 121.72(17) . . ?
N2 C11 C10 115.01(17) . . ?
C12 C11 C10 123.26(18) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 118.30(19) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
N2 C15 C14 124.5(2) . . ?
N2 C15 H15 117.7 . . ?
C14 C15 H15 117.7 . . ?
C17 C16 C23 117.35(15) . . ?
C17 C16 B1 121.55(15) . . ?
C23 C16 B1 121.07(15) . . ?
C19 C17 C16 120.28(16) . . ?
C19 C17 C18 117.80(16) . . ?
C16 C17 C18 121.86(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 122.43(17) . . ?
C20 C19 H19 118.8 . . ?
C17 C19 H19 118.8 . . ?
C22 C20 C19 117.15(16) . . ?
C22 C20 C21 121.77(18) . . ?
C19 C20 C21 121.08(18) . . ?
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 . . ?
C20 C22 C23 122.57(17) . . ?
C20 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
C22 C23 C16 120.17(16) . . ?
C22 C23 C24 117.22(16) . . ?
C16 C23 C24 122.59(16) . . ?
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 . . ?
C26 C25 C31 117.65(17) . . ?
C26 C25 B1 120.75(15) . . ?
C31 C25 B1 121.54(15) . . ?
C28 C26 C25 120.31(17) . . ?
C28 C26 C27 117.39(16) . . ?
C25 C26 C27 122.20(16) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 122.00(18) . . ?
C29 C28 H28 119.0 . . ?
C26 C28 H28 119.0 . . ?
C28 C29 C32 117.62(18) . . ?
C28 C29 C30 120.90(19) . . ?
C32 C29 C30 121.46(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 . . ?
C32 C31 C25 120.10(17) . . ?
C32 C31 C33 119.11(17) . . ?
C25 C31 C33 120.76(17) . . ?
C29 C32 C31 122.17(18) . . ?
C29 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
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 . . ?
C35 C34 C39 120.1(2) . . ?
C35 C34 H34 119.9 . . ?
C39 C34 H34 119.9 . . ?
C34 C35 C36 119.8(3) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C37 C36 C35 120.4(2) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 119.7(2) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C39 C38 C37 119.7(2) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C34 C39 C38 120.2(2) . . ?
C34 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C1 B1 C25 118.01(15) . . ?
C1 B1 C16 121.97(16) . . ?
C25 B1 C16 120.00(15) . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_sy6d
_database_code_depnum_ccdc_archive 'CCDC 1811865'
_audit_update_record             
;
2017-12-17 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H34 B N S'
_chemical_formula_weight         475.47

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   32.54(4)
_cell_length_b                   9.129(10)
_cell_length_c                   9.286(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2759(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3434
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      20.98

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21468
_diffrn_reflns_av_unetI/netI     0.2057
_diffrn_reflns_av_R_equivalents  0.2018
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             5909
_reflns_number_gt                2927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.772
_reflns_Friedel_fraction_full    0.906

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²] 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_abs_structure_details 
; 
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5909
_refine_ls_number_parameters     324
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1957
_refine_ls_R_factor_gt           0.0801
_refine_ls_wR_factor_ref         0.2266
_refine_ls_wR_factor_gt          0.1818
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001

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
S1 S 0.72991(6) 0.2214(2) 0.9515(2) 0.0497(6) Uani 1 1 d . . . . .
N1 N 0.74642(16) 0.5166(8) 0.8998(7) 0.0454(18) Uani 1 1 d . . . . .
B1 B 0.6141(2) 0.6118(10) 0.4778(9) 0.034(2) Uani 1 1 d . . . . .
C1 C 0.64934(17) 0.5754(8) 0.5891(8) 0.0312(17) Uani 1 1 d . . . . .
C2 C 0.67362(19) 0.6907(9) 0.6369(8) 0.0348(18) Uani 1 1 d . . . . .
H2 H 0.6679 0.7863 0.6018 0.042 Uiso 1 1 calc R U . . .
C3 C 0.70660(19) 0.6729(8) 0.7354(8) 0.0361(18) Uani 1 1 d . . . . .
H3 H 0.7231 0.7547 0.7607 0.043 Uiso 1 1 calc R U . . .
C4 C 0.71465(18) 0.5387(9) 0.7940(7) 0.0341(18) Uani 1 1 d . . . . .
C5 C 0.69021(16) 0.4110(8) 0.7547(7) 0.0307(16) Uani 1 1 d . . . . .
C6 C 0.65812(18) 0.4336(9) 0.6471(7) 0.0341(18) Uani 1 1 d . . . . .
C7 C 0.63318(19) 0.3086(9) 0.6116(8) 0.0371(18) Uani 1 1 d . . . . .
H7 H 0.6121 0.3196 0.5418 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6387(2) 0.1754(10) 0.6740(8) 0.043(2) Uani 1 1 d . . . . .
H8 H 0.6218 0.0958 0.6451 0.051 Uiso 1 1 calc R U . . .
C9 C 0.66957(19) 0.1521(9) 0.7833(8) 0.0379(19) Uani 1 1 d . . . . .
C10 C 0.69471(19) 0.2735(9) 0.8196(7) 0.0346(18) Uani 1 1 d . . . . .
C11 C 0.7109(3) 0.0454(10) 0.9542(10) 0.061(2) Uani 1 1 d . . . . .
H11 H 0.7220 -0.0288 1.0145 0.074 Uiso 1 1 calc R U . . .
C12 C 0.6786(2) 0.0205(9) 0.8632(8) 0.045(2) Uani 1 1 d . . . . .
H12 H 0.6644 -0.0698 0.8539 0.054 Uiso 1 1 calc R U . . .
C13 C 0.59060(19) 0.7612(8) 0.5045(8) 0.0328(18) Uani 1 1 d . . . . .
C14 C 0.57143(19) 0.7921(9) 0.6415(8) 0.0381(19) Uani 1 1 d . . . . .
C15 C 0.5748(2) 0.6836(10) 0.7682(9) 0.051(2) Uani 1 1 d . . . . .
H15A H 0.5702 0.5837 0.7332 0.076 Uiso 1 1 calc R U . . .
H15B H 0.5541 0.7078 0.8411 0.076 Uiso 1 1 calc R U . . .
H15C H 0.6023 0.6904 0.8110 0.076 Uiso 1 1 calc R U . . .
C16 C 0.54753(19) 0.9156(9) 0.6600(9) 0.046(2) Uani 1 1 d . . . . .
H16 H 0.5341 0.9304 0.7497 0.055 Uiso 1 1 calc R U . . .
C17 C 0.5424(2) 1.0200(10) 0.5506(10) 0.048(2) Uani 1 1 d . . . . .
C18 C 0.5164(3) 1.1570(12) 0.5737(13) 0.075(3) Uani 1 1 d . . . . .
H18A H 0.5079 1.1966 0.4802 0.112 Uiso 1 1 calc R U . . .
H18B H 0.5326 1.2306 0.6255 0.112 Uiso 1 1 calc R U . . .
H18C H 0.4920 1.1319 0.6302 0.112 Uiso 1 1 calc R U . . .
C19 C 0.5620(2) 0.9927(10) 0.4188(9) 0.047(2) Uani 1 1 d . . . . .
H19 H 0.5589 1.0614 0.3427 0.056 Uiso 1 1 calc R U . . .
C20 C 0.58565(19) 0.8701(9) 0.3960(8) 0.0405(19) Uani 1 1 d . . . . .
C21 C 0.6060(2) 0.8523(11) 0.2483(9) 0.056(2) Uani 1 1 d . . . . .
H21A H 0.5888 0.7898 0.1872 0.085 Uiso 1 1 calc R U . . .
H21B H 0.6331 0.8071 0.2601 0.085 Uiso 1 1 calc R U . . .
H21C H 0.6091 0.9487 0.2031 0.085 Uiso 1 1 calc R U . . .
C22 C 0.60228(18) 0.5087(9) 0.3473(7) 0.0364(19) Uani 1 1 d . . . . .
C23 C 0.56037(19) 0.4750(9) 0.3153(8) 0.0388(19) Uani 1 1 d . . . . .
C24 C 0.52510(18) 0.5398(11) 0.4042(10) 0.060(3) Uani 1 1 d . . . . .
H24A H 0.5232 0.6453 0.3859 0.090 Uiso 1 1 calc R U . . .
H24B H 0.5303 0.5230 0.5068 0.090 Uiso 1 1 calc R U . . .
H24C H 0.4992 0.4926 0.3767 0.090 Uiso 1 1 calc R U . . .
C25 C 0.5509(2) 0.3803(9) 0.2063(8) 0.042(2) Uani 1 1 d . . . . .
H25 H 0.5229 0.3556 0.1911 0.051 Uiso 1 1 calc R U . . .
C26 C 0.5807(2) 0.3179(10) 0.1158(9) 0.047(2) Uani 1 1 d . . . . .
C27 C 0.5691(3) 0.2138(13) -0.0048(10) 0.074(3) Uani 1 1 d . . . . .
H27A H 0.5675 0.2679 -0.0958 0.111 Uiso 1 1 calc R U . . .
H27B H 0.5423 0.1693 0.0162 0.111 Uiso 1 1 calc R U . . .
H27C H 0.5899 0.1367 -0.0129 0.111 Uiso 1 1 calc R U . . .
C28 C 0.6213(2) 0.3541(9) 0.1450(8) 0.044(2) Uani 1 1 d . . . . .
H28 H 0.6421 0.3153 0.0843 0.053 Uiso 1 1 calc R U . . .
C29 C 0.63288(18) 0.4433(9) 0.2574(8) 0.0382(19) Uani 1 1 d . . . . .
C30 C 0.67859(19) 0.4741(11) 0.2791(10) 0.060(3) Uani 1 1 d . . . . .
H30A H 0.6943 0.4301 0.2000 0.091 Uiso 1 1 calc R U . . .
H30B H 0.6876 0.4317 0.3708 0.091 Uiso 1 1 calc R U . . .
H30C H 0.6832 0.5801 0.2804 0.091 Uiso 1 1 calc R U . . .
C31 C 0.7867(2) 0.4816(12) 0.8368(10) 0.070(3) Uani 1 1 d . . . . .
H00D H 0.7838 0.3989 0.7703 0.105 Uiso 1 1 calc R U . . .
H00E H 0.8060 0.4556 0.9137 0.105 Uiso 1 1 calc R U . . .
H00F H 0.7971 0.5671 0.7844 0.105 Uiso 1 1 calc R U . . .
C32 C 0.7495(3) 0.6317(12) 1.0058(10) 0.067(3) Uani 1 1 d . . . . .
H00A H 0.7630 0.7173 0.9628 0.100 Uiso 1 1 calc R U . . .
H00B H 0.7658 0.5972 1.0879 0.100 Uiso 1 1 calc R U . . .
H00C H 0.7220 0.6590 1.0388 0.100 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
S1 C11 1.722(10) . ?
S1 C10 1.743(7) . ?
N1 C32 1.444(11) . ?
N1 C4 1.441(8) . ?
N1 C31 1.471(9) . ?
B1 C1 1.580(10) . ?
B1 C22 1.582(12) . ?
B1 C13 1.583(11) . ?
C1 C2 1.389(10) . ?
C1 C6 1.431(10) . ?
C2 C3 1.420(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.457(10) . ?
C5 C10 1.401(10) . ?
C5 C6 1.460(9) . ?
C6 C7 1.439(10) . ?
C7 C8 1.358(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.445(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(11) . ?
C9 C12 1.443(11) . ?
C11 C12 1.367(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C20 1.425(10) . ?
C13 C14 1.444(10) . ?
C14 C16 1.381(11) . ?
C14 C15 1.542(11) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.404(11) . ?
C16 H16 0.9500 . ?
C17 C19 1.403(12) . ?
C17 C18 1.525(12) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.374(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.532(11) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.429(9) . ?
C22 C29 1.430(10) . ?
C23 C25 1.366(11) . ?
C23 C24 1.533(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.405(11) . ?
C25 H25 0.9500 . ?
C26 C28 1.387(10) . ?
C26 C27 1.517(12) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.377(10) . ?
C28 H28 0.9500 . ?
C29 C30 1.527(9) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H00D 0.9800 . ?
C31 H00E 0.9800 . ?
C31 H00F 0.9800 . ?
C32 H00A 0.9800 . ?
C32 H00B 0.9800 . ?
C32 H00C 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
C11 S1 C10 91.6(4) . . ?
C32 N1 C4 114.4(7) . . ?
C32 N1 C31 111.5(7) . . ?
C4 N1 C31 113.5(6) . . ?
C1 B1 C22 123.6(7) . . ?
C1 B1 C13 115.4(7) . . ?
C22 B1 C13 121.0(6) . . ?
C2 C1 C6 116.9(6) . . ?
C2 C1 B1 117.6(7) . . ?
C6 C1 B1 125.5(6) . . ?
C1 C2 C3 123.3(7) . . ?
C1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C4 C3 C2 120.3(6) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 N1 122.3(6) . . ?
C3 C4 C5 120.9(6) . . ?
N1 C4 C5 116.8(7) . . ?
C10 C5 C4 123.5(6) . . ?
C10 C5 C6 119.7(6) . . ?
C4 C5 C6 116.7(7) . . ?
C1 C6 C7 121.3(6) . . ?
C1 C6 C5 121.9(6) . . ?
C7 C6 C5 116.6(7) . . ?
C8 C7 C6 122.6(7) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 121.5(7) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C12 114.2(7) . . ?
C10 C9 C8 117.0(7) . . ?
C12 C9 C8 128.8(7) . . ?
C5 C10 C9 122.5(6) . . ?
C5 C10 S1 128.0(6) . . ?
C9 C10 S1 109.5(6) . . ?
C12 C11 S1 115.0(7) . . ?
C12 C11 H11 122.5 . . ?
S1 C11 H11 122.5 . . ?
C11 C12 C9 109.7(8) . . ?
C11 C12 H12 125.2 . . ?
C9 C12 H12 125.2 . . ?
C20 C13 C14 116.0(7) . . ?
C20 C13 B1 123.0(7) . . ?
C14 C13 B1 121.0(6) . . ?
C16 C14 C13 120.8(7) . . ?
C16 C14 C15 118.0(7) . . ?
C13 C14 C15 121.1(7) . . ?
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 . . ?
C14 C16 C17 122.1(7) . . ?
C14 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C19 C17 C16 117.1(7) . . ?
C19 C17 C18 121.4(8) . . ?
C16 C17 C18 121.4(8) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 122.3(7) . . ?
C20 C19 H19 118.9 . . ?
C17 C19 H19 118.9 . . ?
C19 C20 C13 121.5(7) . . ?
C19 C20 C21 117.8(7) . . ?
C13 C20 C21 120.7(7) . . ?
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 . . ?
C23 C22 C29 117.0(7) . . ?
C23 C22 B1 121.3(6) . . ?
C29 C22 B1 121.7(5) . . ?
C25 C23 C22 120.4(6) . . ?
C25 C23 C24 118.3(6) . . ?
C22 C23 C24 121.3(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 . . ?
C23 C25 C26 123.0(6) . . ?
C23 C25 H25 118.5 . . ?
C26 C25 H25 118.5 . . ?
C28 C26 C25 116.3(7) . . ?
C28 C26 C27 122.0(7) . . ?
C25 C26 C27 121.6(7) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 123.4(7) . . ?
C29 C28 H28 118.3 . . ?
C26 C28 H28 118.3 . . ?
C28 C29 C22 119.9(6) . . ?
C28 C29 C30 118.4(6) . . ?
C22 C29 C30 121.6(7) . . ?
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 . . ?
N1 C31 H00D 109.5 . . ?
N1 C31 H00E 109.5 . . ?
H00D C31 H00E 109.5 . . ?
N1 C31 H00F 109.5 . . ?
H00D C31 H00F 109.5 . . ?
H00E C31 H00F 109.5 . . ?
N1 C32 H00A 109.5 . . ?
N1 C32 H00B 109.5 . . ?
H00A C32 H00B 109.5 . . ?
N1 C32 H00C 109.5 . . ?
H00A C32 H00C 109.5 . . ?
H00B C32 H00C 109.5 . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_syg33
_database_code_depnum_ccdc_archive 'CCDC 1590113'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H38 B N'
_chemical_formula_weight         471.46

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                   7.868(2)
_cell_length_b                   12.043(4)
_cell_length_c                   16.695(5)
_cell_angle_alpha                69.575(8)
_cell_angle_beta                 77.359(8)
_cell_angle_gamma                76.219(9)
_cell_volume                     1423.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3031
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      21.80

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15953
_diffrn_reflns_av_unetI/netI     0.1664
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.818
_diffrn_reflns_theta_max         27.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6179
_reflns_number_gt                2881
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0900P)²+0.6250P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6179
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2064
_refine_ls_R_factor_gt           0.0900
_refine_ls_wR_factor_ref         0.2380
_refine_ls_wR_factor_gt          0.1975
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
B1 B 0.2672(5) 0.3675(3) 0.2494(3) 0.0298(9) Uani 1 1 d . . . . .
N1 N 0.4113(4) 0.3599(3) 0.57673(19) 0.0447(9) Uani 1 1 d . . . . .
C1 C 0.3223(4) 0.3644(3) 0.3335(2) 0.0289(8) Uani 1 1 d . . . . .
C2 C 0.2269(4) 0.4485(3) 0.3757(2) 0.0326(9) Uani 1 1 d . . . . .
H2A H 0.1397 0.5101 0.3470 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2500(4) 0.4486(3) 0.4546(2) 0.0335(9) Uani 1 1 d . . . . .
H3A H 0.1773 0.5067 0.4797 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3824(4) 0.3620(3) 0.4984(2) 0.0312(8) Uani 1 1 d . . . . .
C5 C 0.4859(4) 0.2800(3) 0.4572(2) 0.0322(9) Uani 1 1 d . . . . .
H5A H 0.5792 0.2231 0.4843 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4579(4) 0.2782(3) 0.3785(2) 0.0286(8) Uani 1 1 d . . . . .
C7 C 0.5756(4) 0.1878(3) 0.3399(2) 0.0318(8) Uani 1 1 d . . . . .
H7A H 0.5984 0.2104 0.2786 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6519(4) 0.0784(3) 0.3830(2) 0.0351(9) Uani 1 1 d . . . . .
H8A H 0.6325 0.0571 0.4443 0.042 Uiso 1 1 calc R U . . .
C9 C 0.7634(4) -0.0130(3) 0.3453(2) 0.0331(9) Uani 1 1 d . . . . .
C10 C 0.8481(5) -0.1189(3) 0.3986(2) 0.0403(10) Uani 1 1 d . . . . .
H10A H 0.8361 -0.1304 0.4587 0.048 Uiso 1 1 calc R U . . .
C11 C 0.9506(5) -0.2087(3) 0.3651(3) 0.0473(11) Uani 1 1 d . . . . .
H11A H 1.0081 -0.2806 0.4024 0.057 Uiso 1 1 calc R U . . .
C12 C 0.9686(5) -0.1941(3) 0.2796(3) 0.0532(12) Uani 1 1 d . . . . .
H12A H 1.0378 -0.2559 0.2571 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8870(6) -0.0905(4) 0.2258(3) 0.0568(12) Uani 1 1 d . . . . .
H13A H 0.9009 -0.0802 0.1658 0.068 Uiso 1 1 calc R U . . .
C14 C 0.7841(5) -0.0001(3) 0.2578(2) 0.0512(12) Uani 1 1 d . . . . .
H14A H 0.7272 0.0711 0.2196 0.061 Uiso 1 1 calc R U . . .
C15 C 0.5296(6) 0.2608(4) 0.6266(3) 0.0646(14) Uani 1 1 d . . . . .
H15A H 0.5340 0.2745 0.6805 0.097 Uiso 1 1 calc R U . . .
H15B H 0.4864 0.1855 0.6399 0.097 Uiso 1 1 calc R U . . .
H15C H 0.6485 0.2553 0.5930 0.097 Uiso 1 1 calc R U . . .
C16 C 0.3077(5) 0.4448(4) 0.6201(2) 0.0521(11) Uani 1 1 d . . . . .
H16A H 0.3495 0.4279 0.6750 0.078 Uiso 1 1 calc R U . . .
H16B H 0.3208 0.5268 0.5834 0.078 Uiso 1 1 calc R U . . .
H16C H 0.1828 0.4371 0.6312 0.078 Uiso 1 1 calc R U . . .
C17 C 0.1701(4) 0.4904(3) 0.1899(2) 0.0295(8) Uani 1 1 d . . . . .
C18 C 0.2474(4) 0.5946(3) 0.1576(2) 0.0295(8) Uani 1 1 d . . . . .
C19 C 0.1701(5) 0.6975(3) 0.0975(2) 0.0379(9) Uani 1 1 d . . . . .
H19A H 0.2259 0.7662 0.0758 0.045 Uiso 1 1 calc R U . . .
C20 C 0.0161(5) 0.7035(4) 0.0683(2) 0.0478(11) Uani 1 1 d . . . . .
C21 C -0.0622(5) 0.6027(4) 0.1021(3) 0.0558(12) Uani 1 1 d . . . . .
H21A H -0.1699 0.6051 0.0841 0.067 Uiso 1 1 calc R U . . .
C22 C 0.0097(5) 0.4971(3) 0.1616(3) 0.0431(10) Uani 1 1 d . . . . .
C23 C -0.0889(5) 0.3923(4) 0.1950(3) 0.0724(15) Uani 1 1 d . . . . .
H23A H -0.0238 0.3247 0.2360 0.109 Uiso 1 1 calc R U . . .
H23B H -0.2072 0.4168 0.2241 0.109 Uiso 1 1 calc R U . . .
H23C H -0.0996 0.3677 0.1464 0.109 Uiso 1 1 calc R U . . .
C24 C 0.4189(5) 0.5997(3) 0.1808(2) 0.0426(10) Uani 1 1 d . . . . .
H24A H 0.4603 0.5231 0.2231 0.064 Uiso 1 1 calc R U . . .
H24B H 0.5076 0.6144 0.1287 0.064 Uiso 1 1 calc R U . . .
H24C H 0.4005 0.6651 0.2056 0.064 Uiso 1 1 calc R U . . .
C25 C -0.0619(7) 0.8160(4) 0.0020(3) 0.0876(18) Uani 1 1 d . . . . .
H25A H 0.0129 0.8771 -0.0138 0.131 Uiso 1 1 calc R U . . .
H25B H -0.0678 0.7967 -0.0496 0.131 Uiso 1 1 calc R U . . .
H25C H -0.1813 0.8471 0.0265 0.131 Uiso 1 1 calc R U . . .
C26 C 0.3034(4) 0.2515(3) 0.2202(2) 0.0282(8) Uani 1 1 d . . . . .
C27 C 0.4026(5) 0.2509(3) 0.1384(2) 0.0318(8) Uani 1 1 d . . . . .
C28 C 0.4347(5) 0.1487(3) 0.1130(2) 0.0382(9) Uani 1 1 d . . . . .
H28A H 0.5043 0.1495 0.0586 0.046 Uiso 1 1 calc R U . . .
C29 C 0.3688(5) 0.0462(3) 0.1640(2) 0.0407(10) Uani 1 1 d . . . . .
C30 C 0.2697(5) 0.0472(3) 0.2430(2) 0.0407(10) Uani 1 1 d . . . . .
H30A H 0.2207 -0.0220 0.2784 0.049 Uiso 1 1 calc R U . . .
C31 C 0.2390(5) 0.1459(3) 0.2727(2) 0.0349(9) Uani 1 1 d . . . . .
C32 C 0.1335(6) 0.1349(4) 0.3612(2) 0.0532(11) Uani 1 1 d . . . . .
H32A H 0.1214 0.2099 0.3742 0.080 Uiso 1 1 calc R U . . .
H32B H 0.0159 0.1196 0.3625 0.080 Uiso 1 1 calc R U . . .
H32C H 0.1947 0.0681 0.4043 0.080 Uiso 1 1 calc R U . . .
C33 C 0.4019(7) -0.0635(3) 0.1345(3) 0.0679(14) Uani 1 1 d . . . . .
H33A H 0.3449 -0.1269 0.1793 0.102 Uiso 1 1 calc R U . . .
H33B H 0.3527 -0.0420 0.0809 0.102 Uiso 1 1 calc R U . . .
H33C H 0.5296 -0.0927 0.1243 0.102 Uiso 1 1 calc R U . . .
C34 C 0.4811(6) 0.3589(3) 0.0785(2) 0.0530(11) Uani 1 1 d . . . . .
H34A H 0.4477 0.4238 0.1047 0.080 Uiso 1 1 calc R U . . .
H34B H 0.6103 0.3367 0.0687 0.080 Uiso 1 1 calc R U . . .
H34C H 0.4362 0.3864 0.0232 0.080 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
B1 C1 1.543(5) . ?
B1 C26 1.580(5) . ?
B1 C17 1.590(5) . ?
N1 C4 1.366(4) . ?
N1 C16 1.447(4) . ?
N1 C15 1.450(4) . ?
C1 C2 1.410(4) . ?
C1 C6 1.435(4) . ?
C2 C3 1.369(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.411(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.399(4) . ?
C5 C6 1.388(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.484(4) . ?
C7 C8 1.329(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.469(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(4) . ?
C9 C14 1.392(5) . ?
C10 C11 1.393(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.355(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.365(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(5) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.408(5) . ?
C17 C22 1.416(5) . ?
C18 C19 1.398(4) . ?
C18 C24 1.503(5) . ?
C19 C20 1.380(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.378(6) . ?
C20 C25 1.513(5) . ?
C21 C22 1.394(5) . ?
C21 H21A 0.9500 . ?
C22 C23 1.514(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C31 1.406(5) . ?
C26 C27 1.418(5) . ?
C27 C28 1.389(5) . ?
C27 C34 1.509(5) . ?
C28 C29 1.377(5) . ?
C28 H28A 0.9500 . ?
C29 C30 1.379(5) . ?
C29 C33 1.513(5) . ?
C30 C31 1.393(5) . ?
C30 H30A 0.9500 . ?
C31 C32 1.506(5) . ?
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 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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 B1 C26 122.0(3) . . ?
C1 B1 C17 119.6(3) . . ?
C26 B1 C17 118.4(3) . . ?
C4 N1 C16 122.4(3) . . ?
C4 N1 C15 120.8(3) . . ?
C16 N1 C15 116.1(3) . . ?
C2 C1 C6 114.2(3) . . ?
C2 C1 B1 119.2(3) . . ?
C6 C1 B1 126.5(3) . . ?
C3 C2 C1 125.2(3) . . ?
C3 C2 H2A 117.4 . . ?
C1 C2 H2A 117.4 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
N1 C4 C5 121.3(3) . . ?
N1 C4 C3 121.5(3) . . ?
C5 C4 C3 117.1(3) . . ?
C6 C5 C4 122.8(3) . . ?
C6 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 C7 118.6(3) . . ?
C1 C6 C7 120.4(3) . . ?
C8 C7 C6 126.2(3) . . ?
C8 C7 H7A 116.9 . . ?
C6 C7 H7A 116.9 . . ?
C7 C8 C9 126.4(3) . . ?
C7 C8 H8A 116.8 . . ?
C9 C8 H8A 116.8 . . ?
C10 C9 C14 117.6(3) . . ?
C10 C9 C8 119.6(3) . . ?
C14 C9 C8 122.8(3) . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C13 C14 C9 120.5(3) . . ?
C13 C14 H14A 119.8 . . ?
C9 C14 H14A 119.8 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 117.2(3) . . ?
C18 C17 B1 121.1(3) . . ?
C22 C17 B1 121.4(3) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 C24 116.7(3) . . ?
C17 C18 C24 123.0(3) . . ?
C20 C19 C18 122.7(4) . . ?
C20 C19 H19A 118.6 . . ?
C18 C19 H19A 118.6 . . ?
C21 C20 C19 116.9(3) . . ?
C21 C20 C25 122.0(4) . . ?
C19 C20 C25 121.1(4) . . ?
C20 C21 C22 122.9(4) . . ?
C20 C21 H21A 118.5 . . ?
C22 C21 H21A 118.5 . . ?
C21 C22 C17 120.0(4) . . ?
C21 C22 C23 118.2(4) . . ?
C17 C22 C23 121.8(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 C26 C27 117.3(3) . . ?
C31 C26 B1 122.2(3) . . ?
C27 C26 B1 120.5(3) . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 C34 118.5(3) . . ?
C26 C27 C34 121.1(3) . . ?
C29 C28 C27 122.1(4) . . ?
C29 C28 H28A 119.0 . . ?
C27 C28 H28A 119.0 . . ?
C28 C29 C30 117.7(3) . . ?
C28 C29 C33 121.4(4) . . ?
C30 C29 C33 120.9(4) . . ?
C29 C30 C31 122.4(3) . . ?
C29 C30 H30A 118.8 . . ?
C31 C30 H30A 118.8 . . ?
C30 C31 C26 120.1(3) . . ?
C30 C31 C32 117.6(3) . . ?
C26 C31 C32 122.3(3) . . ?
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 . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C27 C34 H34A 109.5 . . ?
C27 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C27 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_sy10
_database_code_depnum_ccdc_archive 'CCDC 1590114'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H49 B N2'
_chemical_formula_weight         628.67

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                   11.4473(10)
_cell_length_b                   11.8684(11)
_cell_length_c                   15.9919(15)
_cell_angle_alpha                94.282(4)
_cell_angle_beta                 106.166(3)
_cell_angle_gamma                114.679(3)
_cell_volume                     1850.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2991
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21084
_diffrn_reflns_av_unetI/netI     0.1425
_diffrn_reflns_av_R_equivalents  0.1347
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         27.174
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             8129
_reflns_number_gt                4277
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1024P)²] 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         8129
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2135
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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 N 0.6609(3) 0.2150(2) 0.56680(17) 0.0447(6) Uani 1 1 d . . . . .
C1 C 0.3324(2) 0.1802(2) 0.68608(15) 0.0232(5) Uani 1 1 d . . . . .
B1 B 0.3334(3) 0.3090(2) 0.68139(18) 0.0244(6) Uani 1 1 d . . . . .
C2 C 0.3623(2) 0.1489(2) 0.76702(16) 0.0272(6) Uani 1 1 d . . . . .
H2 H 0.3900 0.2120 0.8184 0.033 Uiso 1 1 calc R U . . .
N2 N 0.3490(2) -0.16539(19) 0.72256(14) 0.0334(5) Uani 1 1 d . . . . .
C3 C 0.3555(3) 0.0296(2) 0.78078(16) 0.0295(6) Uani 1 1 d . . . . .
H3 H 0.3518 0.0059 0.8358 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3544(2) -0.0504(2) 0.71455(16) 0.0276(6) Uani 1 1 d . . . . .
C5 C 0.3665(2) -0.0046(2) 0.63058(16) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.3239 -0.0809 0.5808 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4199(3) 0.1480(2) 0.50692(17) 0.0349(6) Uani 1 1 d . . . . .
H8 H 0.4272 0.1728 0.4527 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3040(3) 0.1168(2) 0.52286(16) 0.0303(6) Uani 1 1 d . . . . .
H7 H 0.2301 0.1220 0.4809 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2881(2) 0.0730(2) 0.60712(15) 0.0239(5) Uani 1 1 d . . . . .
H6 H 0.1889 0.0147 0.5938 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5363(3) 0.1447(2) 0.57125(18) 0.0337(6) Uani 1 1 d . . . . .
C10 C 0.5147(3) 0.0738(2) 0.63706(17) 0.0289(6) Uani 1 1 d . . . . .
C11 C 0.6267(3) 0.0794(2) 0.70046(19) 0.0381(7) Uani 1 1 d . . . . .
H11 H 0.6161 0.0332 0.7461 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7559(3) 0.1534(3) 0.6974(2) 0.0488(8) Uani 1 1 d . . . . .
H12 H 0.8352 0.1592 0.7411 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7669(3) 0.2178(3) 0.6301(2) 0.0525(9) Uani 1 1 d . . . . .
H13 H 0.8558 0.2677 0.6284 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3755(3) -0.2409(2) 0.6615(2) 0.0457(8) Uani 1 1 d . . . . .
H14A H 0.3495 -0.2240 0.6019 0.069 Uiso 1 1 calc R U . . .
H14B H 0.3218 -0.3313 0.6591 0.069 Uiso 1 1 calc R U . . .
H14C H 0.4731 -0.2185 0.6825 0.069 Uiso 1 1 calc R U . . .
C15 C 0.3437(4) -0.2065(3) 0.80552(19) 0.0512(8) Uani 1 1 d . . . . .
H15A H 0.2687 -0.2002 0.8202 0.077 Uiso 1 1 calc R U . . .
H15B H 0.4305 -0.1521 0.8537 0.077 Uiso 1 1 calc R U . . .
H15C H 0.3284 -0.2948 0.7986 0.077 Uiso 1 1 calc R U . . .
C16 C 0.2484(2) 0.3361(2) 0.59584(15) 0.0253(5) Uani 1 1 d . . . . .
C17 C 0.3113(2) 0.4405(2) 0.55887(16) 0.0262(5) Uani 1 1 d . . . . .
C18 C 0.4634(3) 0.5242(2) 0.59546(17) 0.0341(6) Uani 1 1 d . . . . .
H18A H 0.5106 0.4737 0.5880 0.051 Uiso 1 1 calc R U . . .
H18B H 0.4911 0.5606 0.6590 0.051 Uiso 1 1 calc R U . . .
H18C H 0.4877 0.5929 0.5632 0.051 Uiso 1 1 calc R U . . .
C19 C 0.2338(3) 0.4651(2) 0.48594(17) 0.0337(6) Uani 1 1 d . . . . .
H19 H 0.2785 0.5345 0.4614 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0936(3) 0.3921(3) 0.44760(18) 0.0380(7) Uani 1 1 d . . . . .
C21 C 0.0115(3) 0.4227(3) 0.3695(2) 0.0639(10) Uani 1 1 d . . . . .
H21A H 0.0717 0.4729 0.3388 0.096 Uiso 1 1 calc R U . . .
H21B H -0.0294 0.4716 0.3910 0.096 Uiso 1 1 calc R U . . .
H21C H -0.0610 0.3436 0.3280 0.096 Uiso 1 1 calc R U . . .
C22 C 0.0326(3) 0.2909(2) 0.48424(18) 0.0360(6) Uani 1 1 d . . . . .
H22 H -0.0636 0.2396 0.4590 0.043 Uiso 1 1 calc R U . . .
C23 C 0.1052(2) 0.2607(2) 0.55613(17) 0.0290(6) Uani 1 1 d . . . . .
C24 C 0.0276(3) 0.1478(2) 0.59066(19) 0.0371(7) Uani 1 1 d . . . . .
H24A H -0.0682 0.1309 0.5740 0.056 Uiso 1 1 calc R U . . .
H24B H 0.0683 0.1662 0.6558 0.056 Uiso 1 1 calc R U . . .
H24C H 0.0325 0.0732 0.5646 0.056 Uiso 1 1 calc R U . . .
C25 C 0.4226(3) 0.4184(2) 0.76937(16) 0.0274(6) Uani 1 1 d . . . . .
C26 C 0.5650(3) 0.4667(2) 0.80485(17) 0.0319(6) Uani 1 1 d . . . . .
C27 C 0.6442(3) 0.4225(3) 0.76086(19) 0.0435(7) Uani 1 1 d . . . . .
H27A H 0.5824 0.3650 0.7030 0.065 Uiso 1 1 calc R U . . .
H27B H 0.6840 0.3777 0.7991 0.065 Uiso 1 1 calc R U . . .
H27C H 0.7174 0.4962 0.7520 0.065 Uiso 1 1 calc R U . . .
C28 C 0.6399(3) 0.5633(2) 0.88173(17) 0.0400(7) Uani 1 1 d . . . . .
H28 H 0.7365 0.5957 0.9043 0.048 Uiso 1 1 calc R U . . .
C29 C 0.5796(3) 0.6133(2) 0.92604(17) 0.0404(7) Uani 1 1 d . . . . .
C30 C 0.6627(4) 0.7182(3) 1.00915(19) 0.0631(10) Uani 1 1 d . . . . .
H30A H 0.7599 0.7538 1.0161 0.095 Uiso 1 1 calc R U . . .
H30B H 0.6483 0.6837 1.0613 0.095 Uiso 1 1 calc R U . . .
H30C H 0.6338 0.7851 1.0040 0.095 Uiso 1 1 calc R U . . .
C31 C 0.4386(3) 0.5636(2) 0.89239(17) 0.0369(7) Uani 1 1 d . . . . .
H31 H 0.3944 0.5946 0.9233 0.044 Uiso 1 1 calc R U . . .
C32 C 0.3599(3) 0.4697(2) 0.81472(16) 0.0308(6) Uani 1 1 d . . . . .
C33 C 0.2073(3) 0.4196(3) 0.78341(19) 0.0426(7) Uani 1 1 d . . . . .
H33A H 0.1750 0.4282 0.7218 0.064 Uiso 1 1 calc R U . . .
H33B H 0.1833 0.4681 0.8220 0.064 Uiso 1 1 calc R U . . .
H33C H 0.1641 0.3298 0.7860 0.064 Uiso 1 1 calc R U . . .
C34 C 0.7653(3) 0.8141(3) 0.7679(2) 0.0608(9) Uani 1 1 d . . . . .
H34 H 0.6770 0.7458 0.7564 0.073 Uiso 1 1 calc R U . . .
C35 C 0.8192(3) 0.9130(3) 0.8386(2) 0.0586(9) Uani 1 1 d . . . . .
H35 H 0.7684 0.9134 0.8764 0.070 Uiso 1 1 calc R U . . .
C36 C 0.9466(3) 1.0124(3) 0.8557(2) 0.0565(9) Uani 1 1 d . . . . .
H36 H 0.9835 1.0817 0.9049 0.068 Uiso 1 1 calc R U . . .
C37 C 1.0195(3) 1.0110(3) 0.8020(2) 0.0580(9) Uani 1 1 d . . . . .
H37 H 1.1080 1.0792 0.8141 0.070 Uiso 1 1 calc R U . . .
C38 C 0.9663(4) 0.9118(3) 0.7302(2) 0.0614(9) Uani 1 1 d . . . . .
H38 H 1.0175 0.9115 0.6926 0.074 Uiso 1 1 calc R U . . .
C39 C 0.8383(4) 0.8126(3) 0.7131(2) 0.0640(10) Uani 1 1 d . . . . .
H39 H 0.8006 0.7435 0.6636 0.077 Uiso 1 1 calc R U . . .
C40 C 1.0672(4) 0.7486(5) 0.9177(3) 0.0803(13) Uani 1 1 d . . . . .
H40 H 0.9902 0.7494 0.8761 0.096 Uiso 1 1 calc R U . . .
C41 C 1.1769(5) 0.8596(5) 0.9670(3) 0.0854(13) Uani 1 1 d . . . . .
H41 H 1.1781 0.9387 0.9595 0.102 Uiso 1 1 calc R U . . .
C42 C 1.2844(5) 0.8560(5) 1.0270(3) 0.0913(14) Uani 1 1 d . . . . .
H42 H 1.3606 0.9335 1.0622 0.110 Uiso 1 1 calc R U . . .
C43 C 1.2858(5) 0.7450(6) 1.0381(3) 0.0873(14) Uani 1 1 d . . . . .
H43 H 1.3627 0.7452 1.0806 0.105 Uiso 1 1 calc R U . . .
C44 C 1.1784(5) 0.6335(5) 0.9893(3) 0.0806(12) Uani 1 1 d . . . . .
H44 H 1.1793 0.5552 0.9971 0.097 Uiso 1 1 calc R U . . .
C45 C 1.0683(4) 0.6348(5) 0.9283(3) 0.0839(13) Uani 1 1 d . . . . .
H45 H 0.9924 0.5571 0.8932 0.101 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
N1 C13 1.333(4) . ?
N1 C9 1.344(3) . ?
C1 C2 1.364(3) . ?
C1 C6 1.528(3) . ?
C1 B1 1.531(4) . ?
B1 C16 1.584(4) . ?
B1 C25 1.590(3) . ?
C2 C3 1.423(3) . ?
C2 H2 0.9500 . ?
N2 C4 1.357(3) . ?
N2 C14 1.452(3) . ?
N2 C15 1.456(3) . ?
C3 C4 1.362(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.506(3) . ?
C5 C10 1.525(3) . ?
C5 C6 1.532(3) . ?
C5 H5 1.0000 . ?
C8 C7 1.325(3) . ?
C8 C9 1.456(4) . ?
C8 H8 0.9500 . ?
C7 C6 1.510(3) . ?
C7 H7 0.9500 . ?
C6 H6 1.0000 . ?
C9 C10 1.408(4) . ?
C10 C11 1.368(4) . ?
C11 C12 1.387(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
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 C23 1.415(3) . ?
C16 C17 1.416(3) . ?
C17 C19 1.387(4) . ?
C17 C18 1.504(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.383(4) . ?
C19 H19 0.9500 . ?
C20 C22 1.381(4) . ?
C20 C21 1.508(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.509(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.401(3) . ?
C25 C32 1.415(3) . ?
C26 C28 1.394(3) . ?
C26 C27 1.514(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.373(4) . ?
C28 H28 0.9500 . ?
C29 C31 1.384(4) . ?
C29 C30 1.510(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.388(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.502(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.358(4) . ?
C34 C39 1.373(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.373(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.359(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.373(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.377(5) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.359(6) . ?
C40 C45 1.378(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.352(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.349(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.351(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.370(6) . ?
C44 H44 0.9500 . ?
C45 H45 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
C13 N1 C9 116.7(3) . . ?
C2 C1 C6 113.8(2) . . ?
C2 C1 B1 119.4(2) . . ?
C6 C1 B1 126.6(2) . . ?
C1 B1 C16 123.7(2) . . ?
C1 B1 C25 116.8(2) . . ?
C16 B1 C25 119.5(2) . . ?
C1 C2 C3 125.4(2) . . ?
C1 C2 H2 117.3 . . ?
C3 C2 H2 117.3 . . ?
C4 N2 C14 124.3(2) . . ?
C4 N2 C15 119.0(2) . . ?
C14 N2 C15 115.6(2) . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
N2 C4 C3 123.2(2) . . ?
N2 C4 C5 119.3(2) . . ?
C3 C4 C5 117.4(2) . . ?
C4 C5 C10 112.6(2) . . ?
C4 C5 C6 110.79(19) . . ?
C10 C5 C6 109.68(19) . . ?
C4 C5 H5 107.9 . . ?
C10 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C7 C8 C9 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C6 C1 114.29(18) . . ?
C7 C6 C5 108.54(19) . . ?
C1 C6 C5 111.07(19) . . ?
C7 C6 H6 107.6 . . ?
C1 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
N1 C9 C10 123.2(3) . . ?
N1 C9 C8 117.6(2) . . ?
C10 C9 C8 119.1(2) . . ?
C11 C10 C9 118.0(2) . . ?
C11 C10 C5 125.5(2) . . ?
C9 C10 C5 116.5(2) . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
N1 C13 C12 124.3(3) . . ?
N1 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 C16 C17 117.3(2) . . ?
C23 C16 B1 121.2(2) . . ?
C17 C16 B1 121.4(2) . . ?
C19 C17 C16 120.3(2) . . ?
C19 C17 C18 118.6(2) . . ?
C16 C17 C18 121.1(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 122.3(2) . . ?
C20 C19 H19 118.8 . . ?
C17 C19 H19 118.8 . . ?
C22 C20 C19 117.1(2) . . ?
C22 C20 C21 121.7(3) . . ?
C19 C20 C21 121.2(3) . . ?
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 . . ?
C20 C22 C23 123.0(2) . . ?
C20 C22 H22 118.5 . . ?
C23 C22 H22 118.5 . . ?
C22 C23 C16 119.9(2) . . ?
C22 C23 C24 118.4(2) . . ?
C16 C23 C24 121.7(2) . . ?
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 . . ?
C26 C25 C32 117.8(2) . . ?
C26 C25 B1 121.5(2) . . ?
C32 C25 B1 120.8(2) . . ?
C28 C26 C25 119.9(2) . . ?
C28 C26 C27 117.3(2) . . ?
C25 C26 C27 122.7(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 122.5(3) . . ?
C29 C28 H28 118.7 . . ?
C26 C28 H28 118.7 . . ?
C28 C29 C31 117.7(2) . . ?
C28 C29 C30 121.7(3) . . ?
C31 C29 C30 120.6(3) . . ?
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 . . ?
C29 C31 C32 121.9(3) . . ?
C29 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C25 120.2(2) . . ?
C31 C32 C33 118.5(2) . . ?
C25 C32 C33 121.2(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C39 120.1(3) . . ?
C35 C34 H34 120.0 . . ?
C39 C34 H34 120.0 . . ?
C34 C35 C36 120.5(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C37 C36 C35 119.6(3) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C38 120.6(3) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C39 119.5(3) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C34 C39 C38 119.7(3) . . ?
C34 C39 H39 120.2 . . ?
C38 C39 H39 120.2 . . ?
C41 C40 C45 119.7(4) . . ?
C41 C40 H40 120.2 . . ?
C45 C40 H40 120.2 . . ?
C42 C41 C40 119.1(5) . . ?
C42 C41 H41 120.4 . . ?
C40 C41 H41 120.4 . . ?
C43 C42 C41 121.5(5) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C42 C43 C44 120.5(4) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C43 C44 C45 119.0(4) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 H44 120.5 . . ?
C44 C45 C40 120.2(4) . . ?
C44 C45 H45 119.9 . . ?
C40 C45 H45 119.9 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_syg40a
_database_code_depnum_ccdc_archive 'CCDC 1590112'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H35 B N2'
_chemical_formula_weight         470.44

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'

_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                   22.112(6)
_cell_length_b                   8.318(2)
_cell_length_c                   15.429(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.321(8)
_cell_angle_gamma                90
_cell_volume                     2661.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4922
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      21.95

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30375
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_av_R_equivalents  0.1436
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         27.202
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5916
_reflns_number_gt                3131
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0642P)²+4.5585P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0055(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5916
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1778
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.2474
_refine_ls_wR_factor_gt          0.2120
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.022
_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 N 0.0400(2) -0.0377(5) 0.1158(3) 0.0690(12) Uani 1 1 d . . . . .
C1 C 0.24287(19) 0.2103(4) 0.4173(3) 0.0416(9) Uani 1 1 d . . . . .
B1 B 0.3019(2) 0.2968(5) 0.4043(3) 0.0400(11) Uani 1 1 d . . . . .
N2 N 0.09358(16) -0.0329(4) 0.4798(2) 0.0507(9) Uani 1 1 d . . . . .
C2 C 0.2404(2) 0.1990(5) 0.5068(3) 0.0452(10) Uani 1 1 d . . . . .
H2 H 0.2747 0.2449 0.5564 0.054 Uiso 1 1 calc R U . . .
C3 C 0.19142(19) 0.1257(5) 0.5264(3) 0.0470(10) Uani 1 1 d . . . . .
H3 H 0.1921 0.1240 0.5883 0.056 Uiso 1 1 calc R U . . .
C4 C 0.14045(19) 0.0532(5) 0.4570(3) 0.0434(10) Uani 1 1 d . . . . .
C5 C 0.13669(17) 0.0654(4) 0.3629(2) 0.0340(8) Uani 1 1 d . . . . .
C7 C 0.1907(2) 0.1427(4) 0.2526(3) 0.0420(10) Uani 1 1 d . . . . .
H7 H 0.2262 0.1898 0.2409 0.050 Uiso 1 1 calc R U . . .
C6 C 0.18957(19) 0.1431(4) 0.3464(3) 0.0404(9) Uani 1 1 d . . . . .
C9 C 0.0875(2) 0.0147(5) 0.1947(3) 0.0537(11) Uani 1 1 d . . . . .
C8 C 0.1429(2) 0.0777(5) 0.1830(3) 0.0513(11) Uani 1 1 d . . . . .
H8 H 0.1465 0.0739 0.1234 0.062 Uiso 1 1 calc R U . . .
C10 C 0.08296(19) 0.0118(4) 0.2823(3) 0.0424(10) Uani 1 1 d . . . . .
C11 C 0.0211(2) -0.0341(5) 0.2841(3) 0.0550(12) Uani 1 1 d . . . . .
H11 H 0.0131 -0.0303 0.3407 0.066 Uiso 1 1 calc R U . . .
C12 C -0.0259(2) -0.0824(6) 0.2068(4) 0.0685(14) Uani 1 1 d . . . . .
H12 H -0.0666 -0.1144 0.2088 0.082 Uiso 1 1 calc R U . . .
C13 C -0.0143(3) -0.0852(7) 0.1225(4) 0.0765(16) Uani 1 1 d . . . . .
H13 H -0.0474 -0.1232 0.0686 0.092 Uiso 1 1 calc R U . . .
C14 C 0.0894(2) -0.0009(7) 0.5717(3) 0.0699(15) Uani 1 1 d . . . . .
H14A H 0.0855 0.1151 0.5795 0.105 Uiso 1 1 calc R U . . .
H14B H 0.1284 -0.0409 0.6198 0.105 Uiso 1 1 calc R U . . .
H14C H 0.0515 -0.0556 0.5768 0.105 Uiso 1 1 calc R U . . .
C15 C 0.0934(2) -0.2075(5) 0.4649(4) 0.0652(14) Uani 1 1 d . . . . .
H15A H 0.0901 -0.2290 0.4009 0.098 Uiso 1 1 calc R U . . .
H15B H 0.0566 -0.2559 0.4766 0.098 Uiso 1 1 calc R U . . .
H15C H 0.1335 -0.2540 0.5072 0.098 Uiso 1 1 calc R U . . .
C16 C 0.36885(18) 0.2538(4) 0.4773(3) 0.0384(9) Uani 1 1 d . . . . .
C17 C 0.3872(2) 0.0892(4) 0.4980(3) 0.0452(10) Uani 1 1 d . . . . .
C18 C 0.3452(3) -0.0463(5) 0.4415(3) 0.0668(14) Uani 1 1 d . . . . .
H18A H 0.3238 -0.0102 0.3776 0.100 Uiso 1 1 calc R U . . .
H18B H 0.3127 -0.0759 0.4684 0.100 Uiso 1 1 calc R U . . .
H18C H 0.3723 -0.1399 0.4421 0.100 Uiso 1 1 calc R U . . .
C19 C 0.4443(2) 0.0504(5) 0.5661(3) 0.0515(11) Uani 1 1 d . . . . .
H19 H 0.4560 -0.0597 0.5766 0.062 Uiso 1 1 calc R U . . .
C20 C 0.4854(2) 0.1649(5) 0.6199(3) 0.0512(11) Uani 1 1 d . . . . .
C21 C 0.5453(2) 0.1200(7) 0.6986(4) 0.0799(16) Uani 1 1 d . . . . .
H21A H 0.5772 0.0753 0.6741 0.120 Uiso 1 1 calc R U . . .
H21B H 0.5347 0.0395 0.7375 0.120 Uiso 1 1 calc R U . . .
H21C H 0.5633 0.2158 0.7356 0.120 Uiso 1 1 calc R U . . .
C22 C 0.4694(2) 0.3252(5) 0.5991(3) 0.0454(10) Uani 1 1 d . . . . .
H22 H 0.4977 0.4065 0.6338 0.055 Uiso 1 1 calc R U . . .
C23 C 0.41332(19) 0.3695(4) 0.5291(3) 0.0408(10) Uani 1 1 d . . . . .
C24 C 0.4013(2) 0.5480(4) 0.5098(3) 0.0514(11) Uani 1 1 d . . . . .
H24A H 0.4168 0.5800 0.4601 0.077 Uiso 1 1 calc R U . . .
H24B H 0.4243 0.6092 0.5659 0.077 Uiso 1 1 calc R U . . .
H24C H 0.3550 0.5699 0.4911 0.077 Uiso 1 1 calc R U . . .
C25 C 0.29461(18) 0.4291(4) 0.3278(2) 0.0356(9) Uani 1 1 d . . . . .
C26 C 0.33329(18) 0.4258(4) 0.2713(3) 0.0405(9) Uani 1 1 d . . . . .
C27 C 0.3792(2) 0.2877(5) 0.2758(3) 0.0606(13) Uani 1 1 d . . . . .
H27A H 0.3558 0.1856 0.2685 0.091 Uiso 1 1 calc R U . . .
H27B H 0.4144 0.2891 0.3357 0.091 Uiso 1 1 calc R U . . .
H27C H 0.3970 0.2992 0.2262 0.091 Uiso 1 1 calc R U . . .
C28 C 0.3286(2) 0.5473(5) 0.2083(3) 0.0464(10) Uani 1 1 d . . . . .
H28 H 0.3544 0.5416 0.1703 0.056 Uiso 1 1 calc R U . . .
C29 C 0.2875(2) 0.6776(5) 0.1985(3) 0.0452(10) Uani 1 1 d . . . . .
C30 C 0.2846(3) 0.8112(6) 0.1319(3) 0.0734(15) Uani 1 1 d . . . . .
H30A H 0.2838 0.7657 0.0729 0.110 Uiso 1 1 calc R U . . .
H30B H 0.3227 0.8800 0.1572 0.110 Uiso 1 1 calc R U . . .
H30C H 0.2456 0.8750 0.1220 0.110 Uiso 1 1 calc R U . . .
C31 C 0.24961(19) 0.6814(5) 0.2529(3) 0.0437(10) Uani 1 1 d . . . . .
H31 H 0.2214 0.7699 0.2476 0.052 Uiso 1 1 calc R U . . .
C32 C 0.25155(18) 0.5593(4) 0.3153(3) 0.0391(9) Uani 1 1 d . . . . .
C33 C 0.2080(2) 0.5793(5) 0.3717(3) 0.0562(12) Uani 1 1 d . . . . .
H33A H 0.1929 0.6908 0.3674 0.084 Uiso 1 1 calc R U . . .
H33B H 0.2320 0.5528 0.4365 0.084 Uiso 1 1 calc R U . . .
H33C H 0.1709 0.5071 0.3478 0.084 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
N1 C13 1.302(7) . ?
N1 C9 1.374(5) . ?
C1 C2 1.403(5) . ?
C1 C6 1.416(5) . ?
C1 B1 1.563(6) . ?
B1 C16 1.559(6) . ?
B1 C25 1.581(6) . ?
N2 C4 1.401(5) . ?
N2 C15 1.471(5) . ?
N2 C14 1.476(5) . ?
C2 C3 1.366(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.430(5) . ?
C5 C6 1.434(5) . ?
C5 C10 1.459(5) . ?
C7 C8 1.333(5) . ?
C7 C6 1.456(5) . ?
C7 H7 0.9500 . ?
C9 C10 1.391(6) . ?
C9 C8 1.401(6) . ?
C8 H8 0.9500 . ?
C10 C11 1.430(6) . ?
C11 C12 1.343(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.409(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
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 C23 1.409(5) . ?
C16 C17 1.432(5) . ?
C17 C19 1.372(6) . ?
C17 C18 1.526(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.377(6) . ?
C19 H19 0.9500 . ?
C20 C22 1.389(6) . ?
C20 C21 1.501(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.382(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.520(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C32 1.410(5) . ?
C25 C26 1.417(5) . ?
C26 C28 1.382(5) . ?
C26 C27 1.518(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.388(6) . ?
C28 H28 0.9500 . ?
C29 C31 1.377(6) . ?
C29 C30 1.500(6) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.389(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.515(5) . ?
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
C13 N1 C9 117.9(4) . . ?
C2 C1 C6 115.3(4) . . ?
C2 C1 B1 118.5(4) . . ?
C6 C1 B1 126.2(4) . . ?
C16 B1 C1 115.3(3) . . ?
C16 B1 C25 121.6(3) . . ?
C1 B1 C25 122.9(4) . . ?
C4 N2 C15 115.2(3) . . ?
C4 N2 C14 116.6(3) . . ?
C15 N2 C14 109.3(4) . . ?
C3 C2 C1 123.6(4) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 N2 120.0(4) . . ?
C3 C4 C5 119.7(4) . . ?
N2 C4 C5 120.3(4) . . ?
C4 C5 C6 116.7(3) . . ?
C4 C5 C10 125.9(3) . . ?
C6 C5 C10 117.4(3) . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C1 C6 C5 123.5(3) . . ?
C1 C6 C7 118.2(4) . . ?
C5 C6 C7 118.2(3) . . ?
N1 C9 C10 124.4(4) . . ?
N1 C9 C8 116.0(4) . . ?
C10 C9 C8 119.6(4) . . ?
C7 C8 C9 122.2(4) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C9 C10 C11 114.6(4) . . ?
C9 C10 C5 120.7(4) . . ?
C11 C10 C5 124.5(4) . . ?
C12 C11 C10 120.8(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.5(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
N1 C13 C12 122.4(5) . . ?
N1 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 C16 C17 116.0(4) . . ?
C23 C16 B1 123.6(3) . . ?
C17 C16 B1 120.3(4) . . ?
C19 C17 C16 120.6(4) . . ?
C19 C17 C18 118.6(4) . . ?
C16 C17 C18 120.7(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 122.6(4) . . ?
C17 C19 H19 118.7 . . ?
C20 C19 H19 118.7 . . ?
C19 C20 C22 117.6(4) . . ?
C19 C20 C21 121.9(4) . . ?
C22 C20 C21 120.6(4) . . ?
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 . . ?
C23 C22 C20 121.6(4) . . ?
C23 C22 H22 119.2 . . ?
C20 C22 H22 119.2 . . ?
C22 C23 C16 121.4(3) . . ?
C22 C23 C24 117.5(4) . . ?
C16 C23 C24 121.1(4) . . ?
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 . . ?
C32 C25 C26 117.0(3) . . ?
C32 C25 B1 121.7(3) . . ?
C26 C25 B1 121.2(3) . . ?
C28 C26 C25 120.3(4) . . ?
C28 C26 C27 118.1(4) . . ?
C25 C26 C27 121.5(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 122.2(4) . . ?
C26 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
C31 C29 C28 117.8(4) . . ?
C31 C29 C30 120.7(4) . . ?
C28 C29 C30 121.5(4) . . ?
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 . . ?
C29 C31 C32 121.7(4) . . ?
C29 C31 H31 119.1 . . ?
C32 C31 H31 119.1 . . ?
C31 C32 C25 120.9(4) . . ?
C31 C32 C33 116.4(3) . . ?
C25 C32 C33 122.6(3) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_sy22
_database_code_depnum_ccdc_archive 'CCDC 1816881'
_audit_update_record             
;
2018-01-14 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.18 H3.28 B0.10 N0.10'
_chemical_formula_weight         44.04

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      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                   11.8634(7)
_cell_length_b                   11.8780(8)
_cell_length_c                   18.2134(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.179(2)
_cell_angle_gamma                90
_cell_volume                     2564.7(3)
_cell_formula_units_Z            39
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.83

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.358
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47866
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.645
_diffrn_reflns_theta_max         27.173
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5664
_reflns_number_gt                4083
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0700P)²+0.8000P] 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         5664
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1595
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.62163(14) 0.72318(14) 0.92390(9) 0.0319(4) Uani 1 1 d . . . . .
N1 N 1.09237(14) 0.85607(19) 1.10126(10) 0.0715(6) Uani 1 1 d . . . . .
C1 C 0.60631(13) 0.74775(13) 1.00802(8) 0.0321(3) Uani 1 1 d . . . . .
C2 C 0.49906(13) 0.72707(13) 1.03500(9) 0.0370(4) Uani 1 1 d . . . . .
H2A H 0.4396 0.7084 1.0016 0.044 Uiso 1 1 calc R U . . .
C3 C 0.47784(15) 0.73315(15) 1.10896(9) 0.0435(4) Uani 1 1 d . . . . .
H3A H 0.4058 0.7158 1.1256 0.052 Uiso 1 1 calc R U . . .
C4 C 0.56299(16) 0.76478(16) 1.15807(9) 0.0472(4) Uani 1 1 d . . . . .
H4A H 0.5493 0.7688 1.2085 0.057 Uiso 1 1 calc R U . . .
C5 C 0.66825(15) 0.79055(15) 1.13348(9) 0.0435(4) Uani 1 1 d . . . . .
H5A H 0.7247 0.8152 1.1673 0.052 Uiso 1 1 calc R U . . .
C6 C 0.69301(13) 0.78082(13) 1.05911(8) 0.0351(4) Uani 1 1 d . . . . .
C7 C 0.80619(14) 0.80717(15) 1.03497(9) 0.0408(4) Uani 1 1 d . . . . .
H7A H 0.8126 0.8216 0.9845 0.049 Uiso 1 1 calc R U . . .
C8 C 0.89965(15) 0.81304(19) 1.07548(10) 0.0552(5) Uani 1 1 d . . . . .
H8A H 0.8936 0.8014 1.1262 0.066 Uiso 1 1 calc R U . . .
C9 C 1.01246(15) 0.83593(18) 1.04942(11) 0.0525(5) Uani 1 1 d . . . . .
C10 C 1.0369(2) 0.8360(3) 0.97669(13) 0.1028(12) Uani 1 1 d . . . . .
H10A H 0.9798 0.8211 0.9408 0.123 Uiso 1 1 calc R U . . .
C11 C 1.1454(2) 0.8580(3) 0.95603(15) 0.1124(13) Uani 1 1 d . . . . .
H11A H 1.1625 0.8592 0.9061 0.135 Uiso 1 1 calc R U . . .
C12 C 1.22667(17) 0.8778(2) 1.00835(15) 0.0707(6) Uani 1 1 d . . . . .
H12A H 1.3016 0.8918 0.9960 0.085 Uiso 1 1 calc R U . . .
C13 C 1.19654(18) 0.8768(2) 1.07882(15) 0.0744(7) Uani 1 1 d . . . . .
H13A H 1.2530 0.8917 1.1151 0.089 Uiso 1 1 calc R U . . .
C14 C 0.51504(12) 0.74910(13) 0.87180(8) 0.0312(3) Uani 1 1 d . . . . .
C15 C 0.47312(13) 0.85977(14) 0.86483(8) 0.0367(4) Uani 1 1 d . . . . .
C16 C 0.53341(16) 0.95897(15) 0.89961(11) 0.0504(5) Uani 1 1 d . . . . .
H16A H 0.4799 1.0048 0.9253 0.076 Uiso 1 1 calc R U . . .
H16B H 0.5674 1.0037 0.8618 0.076 Uiso 1 1 calc R U . . .
H16C H 0.5917 0.9324 0.9341 0.076 Uiso 1 1 calc R U . . .
C17 C 0.37526(14) 0.88100(16) 0.82298(9) 0.0445(4) Uani 1 1 d . . . . .
H17A H 0.3500 0.9557 0.8178 0.053 Uiso 1 1 calc R U . . .
C18 C 0.31378(14) 0.79598(17) 0.78864(9) 0.0450(4) Uani 1 1 d . . . . .
C19 C 0.20597(18) 0.8223(2) 0.74488(13) 0.0721(7) Uani 1 1 d . . . . .
H19A H 0.1562 0.8660 0.7749 0.108 Uiso 1 1 calc R U . . .
H19B H 0.1690 0.7526 0.7302 0.108 Uiso 1 1 calc R U . . .
H19C H 0.2236 0.8653 0.7015 0.108 Uiso 1 1 calc R U . . .
C20 C 0.35423(14) 0.68730(16) 0.79579(9) 0.0424(4) Uani 1 1 d . . . . .
H20A H 0.3132 0.6282 0.7731 0.051 Uiso 1 1 calc R U . . .
C21 C 0.45381(13) 0.66239(14) 0.83549(8) 0.0354(4) Uani 1 1 d . . . . .
C22 C 0.49093(17) 0.54173(15) 0.84056(11) 0.0524(5) Uani 1 1 d . . . . .
H22A H 0.4427 0.4959 0.8084 0.079 Uiso 1 1 calc R U . . .
H22B H 0.4856 0.5157 0.8908 0.079 Uiso 1 1 calc R U . . .
H22C H 0.5684 0.5356 0.8258 0.079 Uiso 1 1 calc R U . . .
C23 C 0.73379(13) 0.66878(14) 0.89586(9) 0.0369(4) Uani 1 1 d . . . . .
C24 C 0.79420(13) 0.71993(16) 0.83905(9) 0.0424(4) Uani 1 1 d . . . . .
C25 C 0.75977(16) 0.83177(17) 0.80697(10) 0.0520(5) Uani 1 1 d . . . . .
H25A H 0.7980 0.8438 0.7615 0.078 Uiso 1 1 calc R U . . .
H25B H 0.7803 0.8912 0.8415 0.078 Uiso 1 1 calc R U . . .
H25C H 0.6788 0.8326 0.7972 0.078 Uiso 1 1 calc R U . . .
C26 C 0.89316(15) 0.67123(19) 0.81565(11) 0.0559(5) Uani 1 1 d . . . . .
H26A H 0.9321 0.7063 0.7779 0.067 Uiso 1 1 calc R U . . .
C27 C 0.93608(16) 0.5733(2) 0.84597(13) 0.0648(6) Uani 1 1 d . . . . .
C28 C 1.0443(2) 0.5211(3) 0.81935(18) 0.1041(10) Uani 1 1 d . . . . .
H28A H 1.0503 0.5356 0.7672 0.156 Uiso 1 1 calc R U . . .
H28B H 1.0431 0.4405 0.8278 0.156 Uiso 1 1 calc R U . . .
H28C H 1.1086 0.5538 0.8460 0.156 Uiso 1 1 calc R U . . .
C29 C 0.87847(16) 0.52377(18) 0.90208(13) 0.0610(6) Uani 1 1 d . . . . .
H29A H 0.9071 0.4572 0.9236 0.073 Uiso 1 1 calc R U . . .
C30 C 0.77895(14) 0.56955(15) 0.92784(10) 0.0448(4) Uani 1 1 d . . . . .
C31 C 0.72286(17) 0.50837(17) 0.98937(12) 0.0595(5) Uani 1 1 d . . . . .
H31D H 0.7513 0.4319 0.9926 0.089 Uiso 1 1 calc R U . . .
H31A H 0.6419 0.5068 0.9796 0.089 Uiso 1 1 calc R U . . .
H31B H 0.7393 0.5471 1.0354 0.089 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
B1 C1 1.577(2) . ?
B1 C23 1.581(2) . ?
B1 C14 1.582(2) . ?
N1 C9 1.334(2) . ?
N1 C13 1.339(3) . ?
C1 C2 1.403(2) . ?
C1 C6 1.416(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.376(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.402(2) . ?
C6 C7 1.463(2) . ?
C7 C8 1.310(2) . ?
C8 C9 1.462(3) . ?
C9 C10 1.367(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.351(3) . ?
C12 C13 1.345(3) . ?
C14 C15 1.409(2) . ?
C14 C21 1.410(2) . ?
C15 C17 1.387(2) . ?
C15 C16 1.506(2) . ?
C17 C18 1.381(3) . ?
C18 C20 1.382(3) . ?
C18 C19 1.514(2) . ?
C20 C21 1.393(2) . ?
C21 C22 1.501(2) . ?
C23 C30 1.411(2) . ?
C23 C24 1.418(2) . ?
C24 C26 1.390(3) . ?
C24 C25 1.502(3) . ?
C26 C27 1.377(3) . ?
C27 C29 1.382(3) . ?
C27 C28 1.522(3) . ?
C29 C30 1.397(3) . ?
C30 C31 1.511(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
C1 B1 C23 121.25(14) . . ?
C1 B1 C14 115.32(13) . . ?
C23 B1 C14 123.30(13) . . ?
C9 N1 C13 117.1(2) . . ?
C2 C1 C6 117.66(14) . . ?
C2 C1 B1 116.57(14) . . ?
C6 C1 B1 125.60(13) . . ?
C3 C2 C1 122.24(16) . . ?
C4 C3 C2 119.45(16) . . ?
C3 C4 C5 120.12(15) . . ?
C4 C5 C6 121.47(16) . . ?
C5 C6 C1 118.96(15) . . ?
C5 C6 C7 120.10(15) . . ?
C1 C6 C7 120.93(14) . . ?
C8 C7 C6 127.51(16) . . ?
C7 C8 C9 126.33(17) . . ?
N1 C9 C10 120.98(19) . . ?
N1 C9 C8 115.98(18) . . ?
C10 C9 C8 123.04(18) . . ?
C9 C10 C11 119.9(2) . . ?
C12 C11 C10 119.3(2) . . ?
C13 C12 C11 117.6(2) . . ?
N1 C13 C12 125.1(2) . . ?
C15 C14 C21 117.73(14) . . ?
C15 C14 B1 120.45(13) . . ?
C21 C14 B1 121.65(14) . . ?
C17 C15 C14 120.26(15) . . ?
C17 C15 C16 117.59(15) . . ?
C14 C15 C16 122.12(14) . . ?
C18 C17 C15 122.16(17) . . ?
C17 C18 C20 117.70(15) . . ?
C17 C18 C19 120.54(18) . . ?
C20 C18 C19 121.76(18) . . ?
C18 C20 C21 122.14(16) . . ?
C20 C21 C14 119.98(15) . . ?
C20 C21 C22 118.40(15) . . ?
C14 C21 C22 121.58(15) . . ?
C30 C23 C24 117.68(15) . . ?
C30 C23 B1 121.26(15) . . ?
C24 C23 B1 121.03(15) . . ?
C26 C24 C23 120.11(18) . . ?
C26 C24 C25 117.99(17) . . ?
C23 C24 C25 121.70(15) . . ?
C27 C26 C24 122.17(19) . . ?
C26 C27 C29 118.06(18) . . ?
C26 C27 C28 121.3(2) . . ?
C29 C27 C28 120.6(3) . . ?
C27 C29 C30 122.0(2) . . ?
C29 C30 C23 119.93(18) . . ?
C29 C30 C31 117.61(18) . . ?
C23 C30 C31 122.46(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
C23 B1 C1 C2 -141.10(15) . . . . ?
C14 B1 C1 C2 35.01(19) . . . . ?
C23 B1 C1 C6 34.1(2) . . . . ?
C14 B1 C1 C6 -149.79(15) . . . . ?
C6 C1 C2 C3 -2.9(2) . . . . ?
B1 C1 C2 C3 172.67(15) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -2.8(3) . . . . ?
C4 C5 C6 C1 2.4(3) . . . . ?
C4 C5 C6 C7 -179.04(16) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
B1 C1 C6 C5 -174.73(15) . . . . ?
C2 C1 C6 C7 -178.14(15) . . . . ?
B1 C1 C6 C7 6.7(2) . . . . ?
C5 C6 C7 C8 18.7(3) . . . . ?
C1 C6 C7 C8 -162.76(19) . . . . ?
C6 C7 C8 C9 177.81(19) . . . . ?
C13 N1 C9 C10 0.3(4) . . . . ?
C13 N1 C9 C8 179.7(2) . . . . ?
C7 C8 C9 N1 169.5(2) . . . . ?
C7 C8 C9 C10 -11.2(4) . . . . ?
N1 C9 C10 C11 -0.5(5) . . . . ?
C8 C9 C10 C11 -179.8(3) . . . . ?
C9 C10 C11 C12 0.9(6) . . . . ?
C10 C11 C12 C13 -1.1(5) . . . . ?
C9 N1 C13 C12 -0.6(4) . . . . ?
C11 C12 C13 N1 1.0(4) . . . . ?
C1 B1 C14 C15 62.88(18) . . . . ?
C23 B1 C14 C15 -121.10(17) . . . . ?
C1 B1 C14 C21 -112.14(16) . . . . ?
C23 B1 C14 C21 63.9(2) . . . . ?
C21 C14 C15 C17 -0.5(2) . . . . ?
B1 C14 C15 C17 -175.68(14) . . . . ?
C21 C14 C15 C16 -178.34(15) . . . . ?
B1 C14 C15 C16 6.4(2) . . . . ?
C14 C15 C17 C18 1.9(2) . . . . ?
C16 C15 C17 C18 179.87(17) . . . . ?
C15 C17 C18 C20 -1.4(3) . . . . ?
C15 C17 C18 C19 178.58(17) . . . . ?
C17 C18 C20 C21 -0.5(3) . . . . ?
C19 C18 C20 C21 179.51(17) . . . . ?
C18 C20 C21 C14 1.9(2) . . . . ?
C18 C20 C21 C22 179.72(16) . . . . ?
C15 C14 C21 C20 -1.4(2) . . . . ?
B1 C14 C21 C20 173.79(14) . . . . ?
C15 C14 C21 C22 -179.12(15) . . . . ?
B1 C14 C21 C22 -4.0(2) . . . . ?
C1 B1 C23 C30 51.0(2) . . . . ?
C14 B1 C23 C30 -124.76(16) . . . . ?
C1 B1 C23 C24 -127.16(16) . . . . ?
C14 B1 C23 C24 57.0(2) . . . . ?
C30 C23 C24 C26 1.2(2) . . . . ?
B1 C23 C24 C26 179.44(15) . . . . ?
C30 C23 C24 C25 -173.57(15) . . . . ?
B1 C23 C24 C25 4.7(2) . . . . ?
C23 C24 C26 C27 0.0(3) . . . . ?
C25 C24 C26 C27 174.91(18) . . . . ?
C24 C26 C27 C29 -0.8(3) . . . . ?
C24 C26 C27 C28 179.7(2) . . . . ?
C26 C27 C29 C30 0.5(3) . . . . ?
C28 C27 C29 C30 180.0(2) . . . . ?
C27 C29 C30 C23 0.6(3) . . . . ?
C27 C29 C30 C31 179.94(18) . . . . ?
C24 C23 C30 C29 -1.5(2) . . . . ?
B1 C23 C30 C29 -179.72(16) . . . . ?
C24 C23 C30 C31 179.26(16) . . . . ?
B1 C23 C30 C31 1.0(2) . . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.038

