# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_AS001_cmpd24
_database_code_depnum_ccdc_archive 'CCDC 1914228'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H39 B N2'
_chemical_formula_sum            'C27 H39 B N2'
_chemical_formula_weight         402.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   17.467(4)
_cell_length_b                   9.736(2)
_cell_length_c                   14.482(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2462.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    8596
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.44

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28757
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         28.951
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6169
_reflns_number_gt                4740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    1.000

_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    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0339P)²+0.2797P] 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_abs_structure_details 
;
 Flack x determined using 1827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6169
_refine_ls_number_parameters     350
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.017
_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 0.06942(10) 0.43919(19) 0.53455(12) 0.0241(4) Uani 1 1 d . . . . .
B1 B 0.24774(15) 0.5797(3) 0.40436(17) 0.0237(5) Uani 1 1 d . . . . .
H1B H 0.2412(13) 0.467(2) 0.3692(17) 0.028 Uiso 1 1 d . U . . .
C1 C 0.19343(12) 0.5781(2) 0.49578(16) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.12881(12) 0.5247(2) 0.53810(14) 0.0220(5) Uani 1 1 d . . . . .
C3 C 0.17029(12) 0.6274(2) 0.58102(15) 0.0240(5) Uani 1 1 d D . . . .
C4 C 0.06664(13) 0.3370(2) 0.45842(16) 0.0263(5) Uani 1 1 d . . . . .
H4 H 0.019197 0.281058 0.467319 0.032 Uiso 1 1 calc R U . . .
C5 C 0.13413(14) 0.2388(2) 0.46197(19) 0.0372(6) Uani 1 1 d . . . . .
H5A H 0.181677 0.289785 0.451243 0.056 Uiso 1 1 calc R U . . .
H5B H 0.128120 0.168358 0.414172 0.056 Uiso 1 1 calc R U . . .
H5C H 0.136152 0.194828 0.522801 0.056 Uiso 1 1 calc R U . . .
C6 C 0.05962(14) 0.4082(3) 0.36560(16) 0.0334(6) Uani 1 1 d . . . . .
H6A H 0.012901 0.463943 0.364612 0.050 Uiso 1 1 calc R U . . .
H6B H 0.057212 0.339181 0.316452 0.050 Uiso 1 1 calc R U . . .
H6C H 0.104208 0.467558 0.355813 0.050 Uiso 1 1 calc R U . . .
C7 C 0.01547(13) 0.4300(2) 0.61371(16) 0.0274(5) Uani 1 1 d . . . . .
H7 H 0.016754 0.520854 0.645888 0.033 Uiso 1 1 calc R U . . .
C8 C -0.06656(13) 0.4064(3) 0.58293(19) 0.0358(6) Uani 1 1 d . . . . .
H8A H -0.080306 0.474367 0.535843 0.054 Uiso 1 1 calc R U . . .
H8B H -0.100918 0.415799 0.636054 0.054 Uiso 1 1 calc R U . . .
H8C H -0.071419 0.313837 0.557022 0.054 Uiso 1 1 calc R U . . .
C9 C 0.04123(15) 0.3231(3) 0.68308(17) 0.0418(7) Uani 1 1 d . . . . .
H9A H 0.040654 0.232171 0.654066 0.063 Uiso 1 1 calc R U . . .
H9B H 0.006435 0.323482 0.736158 0.063 Uiso 1 1 calc R U . . .
H9C H 0.093272 0.344493 0.703877 0.063 Uiso 1 1 calc R U . . .
N2A N 0.1776(2) 0.7133(4) 0.6524(2) 0.0286(8) Uani 0.874(6) 1 d D U P A 1
C10A C 0.1277(2) 0.7030(4) 0.7351(2) 0.0372(9) Uani 0.874(6) 1 d D U P A 1
H10A H 0.089796 0.628057 0.723114 0.045 Uiso 0.874(6) 1 calc R U P A 1
C11A C 0.0825(2) 0.8347(5) 0.7504(3) 0.0472(11) Uani 0.874(6) 1 d D U P A 1
H11A H 0.117974 0.910330 0.763204 0.071 Uiso 0.874(6) 1 calc R U P A 1
H11B H 0.047767 0.822740 0.802867 0.071 Uiso 0.874(6) 1 calc R U P A 1
H11C H 0.052740 0.855858 0.694798 0.071 Uiso 0.874(6) 1 calc R U P A 1
C12A C 0.1738(3) 0.6616(5) 0.8196(3) 0.0474(11) Uani 0.874(6) 1 d D U P A 1
H12A H 0.202394 0.577323 0.806238 0.071 Uiso 0.874(6) 1 calc R U P A 1
H12B H 0.139041 0.645427 0.871629 0.071 Uiso 0.874(6) 1 calc R U P A 1
H12C H 0.209650 0.735301 0.835468 0.071 Uiso 0.874(6) 1 calc R U P A 1
C13A C 0.23870(17) 0.8202(3) 0.6523(2) 0.0268(7) Uani 0.874(6) 1 d D U P A 1
H13A H 0.230371 0.879613 0.707773 0.032 Uiso 0.874(6) 1 calc R U P A 1
C14A C 0.3181(2) 0.7566(3) 0.6613(3) 0.0286(8) Uani 0.874(6) 1 d D U P A 1
H14A H 0.320618 0.701682 0.717945 0.043 Uiso 0.874(6) 1 calc R U P A 1
H14B H 0.356661 0.829709 0.663974 0.043 Uiso 0.874(6) 1 calc R U P A 1
H14C H 0.328183 0.697655 0.607854 0.043 Uiso 0.874(6) 1 calc R U P A 1
C15A C 0.2319(3) 0.9118(4) 0.5674(3) 0.0293(9) Uani 0.874(6) 1 d D U P A 1
H15A H 0.241367 0.857129 0.511723 0.044 Uiso 0.874(6) 1 calc R U P A 1
H15B H 0.269577 0.986067 0.571214 0.044 Uiso 0.874(6) 1 calc R U P A 1
H15C H 0.180238 0.950975 0.564587 0.044 Uiso 0.874(6) 1 calc R U P A 1
N2B N 0.1980(15) 0.716(3) 0.6417(17) 0.031(5) Uani 0.126(6) 1 d D U P A 2
C10B C 0.1565(13) 0.730(2) 0.7253(16) 0.035(4) Uani 0.126(6) 1 d D U P A 2
H10B H 0.186389 0.803024 0.758112 0.042 Uiso 0.126(6) 1 calc R U P A 2
C11B C 0.0780(13) 0.795(3) 0.7186(19) 0.039(5) Uani 0.126(6) 1 d D U P A 2
H11D H 0.082547 0.887209 0.692136 0.059 Uiso 0.126(6) 1 calc R U P A 2
H11E H 0.055322 0.801158 0.780372 0.059 Uiso 0.126(6) 1 calc R U P A 2
H11F H 0.045224 0.738379 0.678977 0.059 Uiso 0.126(6) 1 calc R U P A 2
C12B C 0.1616(17) 0.611(3) 0.7921(17) 0.043(5) Uani 0.126(6) 1 d D U P A 2
H12D H 0.129606 0.535273 0.769719 0.065 Uiso 0.126(6) 1 calc R U P A 2
H12E H 0.143535 0.640318 0.853033 0.065 Uiso 0.126(6) 1 calc R U P A 2
H12F H 0.214854 0.580291 0.796614 0.065 Uiso 0.126(6) 1 calc R U P A 2
C13B C 0.2616(12) 0.807(2) 0.6138(16) 0.033(4) Uani 0.126(6) 1 d D U P A 2
H13B H 0.282200 0.771206 0.554186 0.040 Uiso 0.126(6) 1 calc R U P A 2
C14B C 0.3269(15) 0.802(3) 0.6835(19) 0.039(6) Uani 0.126(6) 1 d D U P A 2
H14D H 0.314873 0.861986 0.735947 0.059 Uiso 0.126(6) 1 calc R U P A 2
H14E H 0.374265 0.833637 0.653994 0.059 Uiso 0.126(6) 1 calc R U P A 2
H14F H 0.333549 0.707678 0.705261 0.059 Uiso 0.126(6) 1 calc R U P A 2
C15B C 0.230(2) 0.949(2) 0.594(3) 0.047(6) Uani 0.126(6) 1 d D U P A 2
H15D H 0.184286 0.941269 0.555763 0.070 Uiso 0.126(6) 1 calc R U P A 2
H15E H 0.268895 1.003651 0.561970 0.070 Uiso 0.126(6) 1 calc R U P A 2
H15F H 0.216901 0.994095 0.652728 0.070 Uiso 0.126(6) 1 calc R U P A 2
C16 C 0.33690(12) 0.6015(2) 0.43294(15) 0.0239(5) Uani 1 1 d . . . . .
C17 C 0.37702(13) 0.4946(2) 0.47589(15) 0.0282(5) Uani 1 1 d . . . . .
H17 H 0.352121 0.408779 0.484198 0.034 Uiso 1 1 calc R U . . .
C18 C 0.45166(14) 0.5094(3) 0.50675(18) 0.0341(6) Uani 1 1 d . . . . .
H18 H 0.476518 0.434981 0.536780 0.041 Uiso 1 1 calc R U . . .
C19 C 0.48989(13) 0.6316(3) 0.49401(18) 0.0347(6) Uani 1 1 d . . . . .
H19 H 0.540986 0.642256 0.515332 0.042 Uiso 1 1 calc R U . . .
C20 C 0.45303(13) 0.7384(3) 0.44987(18) 0.0343(6) Uani 1 1 d . . . . .
H20 H 0.479124 0.822687 0.439776 0.041 Uiso 1 1 calc R U . . .
C21 C 0.37794(12) 0.7231(2) 0.42017(17) 0.0275(5) Uani 1 1 d . . . . .
H21 H 0.353607 0.798011 0.390093 0.033 Uiso 1 1 calc R U . . .
C22 C 0.21611(12) 0.6928(2) 0.33204(15) 0.0245(5) Uani 1 1 d . . . . .
C23 C 0.25267(14) 0.7105(3) 0.24656(17) 0.0336(6) Uani 1 1 d . . . . .
H23 H 0.295574 0.654490 0.232161 0.040 Uiso 1 1 calc R U . . .
C24 C 0.22843(16) 0.8067(3) 0.18244(18) 0.0412(7) Uani 1 1 d . . . . .
H24 H 0.254503 0.815580 0.125177 0.049 Uiso 1 1 calc R U . . .
C25 C 0.16625(17) 0.8899(3) 0.20179(19) 0.0419(7) Uani 1 1 d . . . . .
H25 H 0.150001 0.957075 0.158437 0.050 Uiso 1 1 calc R U . . .
C26 C 0.12795(16) 0.8745(3) 0.28469(18) 0.0384(6) Uani 1 1 d . . . . .
H26 H 0.084760 0.930283 0.298295 0.046 Uiso 1 1 calc R U . . .
C27 C 0.15296(13) 0.7770(2) 0.34808(17) 0.0304(5) Uani 1 1 d . . . . .
H27 H 0.125896 0.767384 0.404606 0.036 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 C2 1.331(3) . ?
N1 C4 1.486(3) . ?
N1 C7 1.487(3) . ?
B1 C22 1.617(3) . ?
B1 C16 1.625(3) . ?
B1 C1 1.629(3) . ?
B1 H1B 1.22(2) . ?
C1 C3 1.385(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.382(3) . ?
C3 N2B 1.32(2) . ?
C3 N2A 1.337(4) . ?
C4 C6 1.518(3) . ?
C4 C5 1.519(3) . ?
C4 H4 1.0000 . ?
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 C9 1.515(3) . ?
C7 C8 1.518(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N2A C10A 1.485(4) . ?
N2A C13A 1.491(4) . ?
C10A C12A 1.519(5) . ?
C10A C11A 1.521(5) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A C15A 1.524(5) . ?
C13A C14A 1.525(4) . ?
C13A H13A 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
N2B C10B 1.42(2) . ?
N2B C13B 1.48(2) . ?
C10B C11B 1.512(16) . ?
C10B C12B 1.513(16) . ?
C10B H10B 1.0000 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B C15B 1.511(16) . ?
C13B C14B 1.523(15) . ?
C13B H13B 1.0000 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16 C21 1.396(3) . ?
C16 C17 1.400(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.394(3) . ?
C22 C23 1.404(3) . ?
C23 C24 1.385(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(3) . ?
C26 H26 0.9500 . ?
C27 H27 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
C2 N1 C4 118.23(18) . . ?
C2 N1 C7 120.12(18) . . ?
C4 N1 C7 120.74(17) . . ?
C22 B1 C16 113.80(19) . . ?
C22 B1 C1 109.53(18) . . ?
C16 B1 C1 110.63(18) . . ?
C22 B1 H1B 108.3(11) . . ?
C16 B1 H1B 108.3(11) . . ?
C1 B1 H1B 106.0(11) . . ?
C3 C1 C2 59.85(15) . . ?
C3 C1 B1 153.0(2) . . ?
C2 C1 B1 146.9(2) . . ?
N1 C2 C3 151.4(2) . . ?
N1 C2 C1 148.5(2) . . ?
C3 C2 C1 60.06(16) . . ?
N2B C3 C2 164.1(10) . . ?
N2A C3 C2 148.3(2) . . ?
N2B C3 C1 135.3(9) . . ?
N2A C3 C1 151.6(2) . . ?
C2 C3 C1 60.09(15) . . ?
N1 C4 C6 110.72(17) . . ?
N1 C4 C5 111.78(19) . . ?
C6 C4 C5 112.4(2) . . ?
N1 C4 H4 107.2 . . ?
C6 C4 H4 107.2 . . ?
C5 C4 H4 107.2 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C9 111.4(2) . . ?
N1 C7 C8 112.40(19) . . ?
C9 C7 C8 111.8(2) . . ?
N1 C7 H7 107.0 . . ?
C9 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 N2A C10A 121.7(3) . . ?
C3 N2A C13A 120.3(3) . . ?
C10A N2A C13A 117.9(3) . . ?
N2A C10A C12A 110.9(3) . . ?
N2A C10A C11A 111.4(3) . . ?
C12A C10A C11A 112.4(3) . . ?
N2A C10A H10A 107.3 . . ?
C12A C10A H10A 107.3 . . ?
C11A C10A H10A 107.3 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N2A C13A C15A 110.7(3) . . ?
N2A C13A C14A 111.6(3) . . ?
C15A C13A C14A 112.2(3) . . ?
N2A C13A H13A 107.4 . . ?
C15A C13A H13A 107.4 . . ?
C14A C13A H13A 107.4 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C3 N2B C10B 116.5(17) . . ?
C3 N2B C13B 119.1(17) . . ?
C10B N2B C13B 123.6(19) . . ?
N2B C10B C11B 117(2) . . ?
N2B C10B C12B 116(2) . . ?
C11B C10B C12B 114(2) . . ?
N2B C10B H10B 102.1 . . ?
C11B C10B H10B 102.1 . . ?
C12B C10B H10B 102.1 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
N2B C13B C15B 109(2) . . ?
N2B C13B C14B 111(2) . . ?
C15B C13B C14B 115(2) . . ?
N2B C13B H13B 106.9 . . ?
C15B C13B H13B 106.9 . . ?
C14B C13B H13B 106.9 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C13B C15B H15D 109.5 . . ?
C13B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C21 C16 C17 115.6(2) . . ?
C21 C16 B1 124.7(2) . . ?
C17 C16 B1 119.7(2) . . ?
C18 C17 C16 122.5(2) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.1(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 122.3(2) . . ?
C20 C21 H21 118.8 . . ?
C16 C21 H21 118.8 . . ?
C27 C22 C23 115.8(2) . . ?
C27 C22 B1 124.3(2) . . ?
C23 C22 B1 120.0(2) . . ?
C24 C23 C22 122.3(2) . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 119.5(2) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 119.7(3) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C22 122.7(2) . . ?
C26 C27 H27 118.7 . . ?
C22 C27 H27 118.7 . . ?

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
C22 B1 C1 C3 -82.4(5) . . . . ?
C16 B1 C1 C3 43.8(5) . . . . ?
C22 B1 C1 C2 88.1(4) . . . . ?
C16 B1 C1 C2 -145.6(3) . . . . ?
C4 N1 C2 C3 -174.8(4) . . . . ?
C7 N1 C2 C3 -5.6(5) . . . . ?
C4 N1 C2 C1 10.1(5) . . . . ?
C7 N1 C2 C1 179.3(3) . . . . ?
C3 C1 C2 N1 177.3(4) . . . . ?
B1 C1 C2 N1 2.2(7) . . . . ?
B1 C1 C2 C3 -175.1(4) . . . . ?
N1 C2 C3 N2B 15(6) . . . . ?
C1 C2 C3 N2B -167(6) . . . . ?
N1 C2 C3 N2A -0.1(8) . . . . ?
C1 C2 C3 N2A 177.0(6) . . . . ?
N1 C2 C3 C1 -177.0(5) . . . . ?
C2 C1 C3 N2B 175(2) . . . . ?
B1 C1 C3 N2B -11(2) . . . . ?
C2 C1 C3 N2A -176.6(6) . . . . ?
B1 C1 C3 N2A -2.6(9) . . . . ?
B1 C1 C3 C2 174.1(5) . . . . ?
C2 N1 C4 C6 -64.4(3) . . . . ?
C7 N1 C4 C6 126.5(2) . . . . ?
C2 N1 C4 C5 61.7(3) . . . . ?
C7 N1 C4 C5 -107.4(2) . . . . ?
C2 N1 C7 C9 -89.3(3) . . . . ?
C4 N1 C7 C9 79.6(3) . . . . ?
C2 N1 C7 C8 144.4(2) . . . . ?
C4 N1 C7 C8 -46.7(3) . . . . ?
C2 C3 N2A C10A 9.1(8) . . . . ?
C1 C3 N2A C10A -176.5(4) . . . . ?
C2 C3 N2A C13A -173.1(3) . . . . ?
C1 C3 N2A C13A 1.3(9) . . . . ?
C3 N2A C10A C12A 113.8(4) . . . . ?
C13A N2A C10A C12A -64.1(5) . . . . ?
C3 N2A C10A C11A -120.2(5) . . . . ?
C13A N2A C10A C11A 61.9(5) . . . . ?
C3 N2A C13A C15A 56.6(5) . . . . ?
C10A N2A C13A C15A -125.4(4) . . . . ?
C3 N2A C13A C14A -69.1(5) . . . . ?
C10A N2A C13A C14A 108.9(4) . . . . ?
C2 C3 N2B C10B -12(8) . . . . ?
C1 C3 N2B C10B -176.4(12) . . . . ?
C2 C3 N2B C13B 178(3) . . . . ?
C1 C3 N2B C13B 13(4) . . . . ?
C3 N2B C10B C11B -67(4) . . . . ?
C13B N2B C10B C11B 103(3) . . . . ?
C3 N2B C10B C12B 72(3) . . . . ?
C13B N2B C10B C12B -118(3) . . . . ?
C3 N2B C13B C15B 102(3) . . . . ?
C10B N2B C13B C15B -67(4) . . . . ?
C3 N2B C13B C14B -129(3) . . . . ?
C10B N2B C13B C14B 61(4) . . . . ?
C22 B1 C16 C21 17.6(3) . . . . ?
C1 B1 C16 C21 -106.2(2) . . . . ?
C22 B1 C16 C17 -164.2(2) . . . . ?
C1 B1 C16 C17 72.0(3) . . . . ?
C21 C16 C17 C18 2.1(3) . . . . ?
B1 C16 C17 C18 -176.2(2) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C21 1.0(4) . . . . ?
C19 C20 C21 C16 -0.2(4) . . . . ?
C17 C16 C21 C20 -1.4(3) . . . . ?
B1 C16 C21 C20 176.8(2) . . . . ?
C16 B1 C22 C27 -123.0(2) . . . . ?
C1 B1 C22 C27 1.4(3) . . . . ?
C16 B1 C22 C23 57.3(3) . . . . ?
C1 B1 C22 C23 -178.3(2) . . . . ?
C27 C22 C23 C24 0.9(3) . . . . ?
B1 C22 C23 C24 -179.4(2) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C23 C24 C25 C26 -1.1(4) . . . . ?
C24 C25 C26 C27 0.8(4) . . . . ?
C25 C26 C27 C22 0.3(4) . . . . ?
C23 C22 C27 C26 -1.1(3) . . . . ?
B1 C22 C27 C26 179.1(2) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_AS002_cmpd25
_database_code_depnum_ccdc_archive 'CCDC 1914229'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H38 B Cl N2'
_chemical_formula_sum            'C27 H38 B Cl N2'
_chemical_formula_weight         436.85

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'
Cl Cl 0.1484 0.1585 '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           1
_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'

_cell_length_a                   6.2971(15)
_cell_length_b                   10.739(3)
_cell_length_c                   18.714(5)
_cell_angle_alpha                92.240(3)
_cell_angle_beta                 91.774(3)
_cell_angle_gamma                94.792(3)
_cell_volume                     1259.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    4398
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.91

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15446
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         29.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             11562
_reflns_number_gt                7858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.811
_reflns_Friedel_fraction_full    0.967

_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    'SHELXT-2014 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0543P)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 2712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11562
_refine_ls_number_parameters     575
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.15808(17) 0.41454(11) 0.22756(7) 0.0265(3) Uani 1 1 d . . . . .
Cl2 Cl 0.68454(19) 0.56655(12) 0.73747(7) 0.0296(3) Uani 1 1 d . . . . .
N1 N 0.6128(6) 0.2069(4) 0.3345(2) 0.0216(9) Uani 1 1 d . . . . .
N2 N 0.6374(7) 0.5527(4) 0.3620(2) 0.0214(9) Uani 1 1 d . . . . .
N3 N 0.1315(7) 0.4383(4) 0.8602(2) 0.0234(10) Uani 1 1 d . . . . .
N4 N 0.1836(6) 0.7837(4) 0.8447(2) 0.0204(9) Uani 1 1 d . . . . .
B1 B 0.8711(8) 0.4262(5) 0.1889(3) 0.0136(11) Uani 1 1 d . . . . .
B2 B 0.4002(8) 0.5621(5) 0.6927(3) 0.0140(11) Uani 1 1 d . . . . .
C1 C 0.7342(7) 0.3992(4) 0.2598(3) 0.0186(10) Uani 1 1 d . . . . .
C2 C 0.6564(7) 0.3205(4) 0.3113(2) 0.0180(10) Uani 1 1 d . . . . .
C3 C 0.6654(7) 0.4490(4) 0.3230(2) 0.0179(10) Uani 1 1 d . . . . .
C4 C 0.6292(8) 0.0943(4) 0.2867(3) 0.0207(11) Uani 1 1 d . . . . .
H4 H 0.596898 0.019740 0.316125 0.025 Uiso 1 1 calc R U . . .
C5 C 0.4620(9) 0.0869(5) 0.2261(3) 0.0338(14) Uani 1 1 d . . . . .
H5A H 0.319910 0.087245 0.245939 0.051 Uiso 1 1 calc R U . . .
H5B H 0.470899 0.009658 0.197075 0.051 Uiso 1 1 calc R U . . .
H5C H 0.487478 0.159097 0.196068 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8529(8) 0.0872(5) 0.2609(3) 0.0273(12) Uani 1 1 d . . . . .
H6A H 0.894208 0.161642 0.234197 0.041 Uiso 1 1 calc R U . . .
H6B H 0.857899 0.012222 0.229566 0.041 Uiso 1 1 calc R U . . .
H6C H 0.951708 0.083050 0.302026 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5379(8) 0.1873(5) 0.4072(3) 0.0220(11) Uani 1 1 d . . . . .
H7 H 0.535743 0.272047 0.431226 0.026 Uiso 1 1 calc R U . . .
C8 C 0.3111(8) 0.1270(5) 0.4064(3) 0.0293(13) Uani 1 1 d . . . . .
H8A H 0.217379 0.177858 0.379273 0.044 Uiso 1 1 calc R U . . .
H8B H 0.263217 0.121311 0.455546 0.044 Uiso 1 1 calc R U . . .
H8C H 0.306280 0.042953 0.383712 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6914(9) 0.1169(5) 0.4509(3) 0.0304(13) Uani 1 1 d . . . . .
H9A H 0.697162 0.032558 0.429479 0.046 Uiso 1 1 calc R U . . .
H9B H 0.642603 0.111132 0.499997 0.046 Uiso 1 1 calc R U . . .
H9C H 0.833863 0.161424 0.451560 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5498(8) 0.5491(5) 0.4347(3) 0.0254(12) Uani 1 1 d . . . . .
H10 H 0.538025 0.638188 0.450690 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3248(8) 0.4855(5) 0.4340(3) 0.0306(13) Uani 1 1 d . . . . .
H11A H 0.227421 0.536608 0.408665 0.046 Uiso 1 1 calc R U . . .
H11B H 0.279624 0.475983 0.483297 0.046 Uiso 1 1 calc R U . . .
H11C H 0.322151 0.402938 0.409630 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7092(9) 0.4983(5) 0.4871(3) 0.0278(12) Uani 1 1 d . . . . .
H12A H 0.740771 0.414460 0.470384 0.042 Uiso 1 1 calc R U . . .
H12B H 0.647911 0.493980 0.534576 0.042 Uiso 1 1 calc R U . . .
H12C H 0.840996 0.553916 0.490044 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6787(9) 0.6748(5) 0.3279(3) 0.0265(12) Uani 1 1 d . . . . .
H13 H 0.736020 0.657775 0.279523 0.032 Uiso 1 1 calc R U . . .
C14 C 0.8475(9) 0.7586(5) 0.3710(3) 0.0323(13) Uani 1 1 d . . . . .
H14A H 0.790847 0.782477 0.417323 0.048 Uiso 1 1 calc R U . . .
H14B H 0.885741 0.833882 0.344732 0.048 Uiso 1 1 calc R U . . .
H14C H 0.974397 0.713230 0.378832 0.048 Uiso 1 1 calc R U . . .
C15 C 0.4730(10) 0.7367(5) 0.3173(3) 0.0353(14) Uani 1 1 d . . . . .
H15A H 0.365875 0.677517 0.292482 0.053 Uiso 1 1 calc R U . . .
H15B H 0.499203 0.810486 0.288541 0.053 Uiso 1 1 calc R U . . .
H15C H 0.420813 0.762286 0.363957 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8480(8) 0.5672(4) 0.1623(2) 0.0191(11) Uani 1 1 d . . . . .
C17 C 0.6476(8) 0.6031(5) 0.1410(3) 0.0248(12) Uani 1 1 d . . . . .
H17 H 0.527330 0.543648 0.141955 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6183(9) 0.7220(5) 0.1186(3) 0.0309(13) Uani 1 1 d . . . . .
H18 H 0.479955 0.742488 0.104143 0.037 Uiso 1 1 calc R U . . .
C19 C 0.7900(9) 0.8111(5) 0.1171(3) 0.0295(13) Uani 1 1 d . . . . .
H19 H 0.770547 0.892943 0.102012 0.035 Uiso 1 1 calc R U . . .
C20 C 0.9906(10) 0.7792(5) 0.1380(3) 0.0338(14) Uani 1 1 d . . . . .
H20 H 1.109524 0.839701 0.137757 0.041 Uiso 1 1 calc R U . . .
C21 C 1.0189(8) 0.6585(5) 0.1594(3) 0.0241(12) Uani 1 1 d . . . . .
H21 H 1.158267 0.637782 0.172451 0.029 Uiso 1 1 calc R U . . .
C22 C 0.8188(7) 0.3207(4) 0.1250(2) 0.0163(10) Uani 1 1 d . . . . .
C23 C 0.9681(8) 0.2480(5) 0.0948(3) 0.0226(11) Uani 1 1 d . . . . .
H23 H 1.111856 0.259497 0.112352 0.027 Uiso 1 1 calc R U . . .
C24 C 0.9148(9) 0.1596(5) 0.0400(3) 0.0288(13) Uani 1 1 d . . . . .
H24 H 1.021550 0.111838 0.020765 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7064(9) 0.1402(5) 0.0130(3) 0.0272(12) Uani 1 1 d . . . . .
H25 H 0.669137 0.079230 -0.024396 0.033 Uiso 1 1 calc R U . . .
C26 C 0.5549(9) 0.2106(5) 0.0415(3) 0.0286(12) Uani 1 1 d . . . . .
H26 H 0.411779 0.198578 0.023354 0.034 Uiso 1 1 calc R U . . .
C27 C 0.6090(8) 0.2995(5) 0.0965(3) 0.0231(11) Uani 1 1 d . . . . .
H27 H 0.501432 0.347146 0.115257 0.028 Uiso 1 1 calc R U . . .
C28 C 0.2634(7) 0.5894(4) 0.7632(2) 0.0177(10) Uani 1 1 d . . . . .
C29 C 0.1831(8) 0.5408(5) 0.8252(3) 0.0199(11) Uani 1 1 d . . . . .
C30 C 0.2024(7) 0.6690(5) 0.8180(2) 0.0189(10) Uani 1 1 d . . . . .
C31 C 0.1522(8) 0.3160(5) 0.8222(3) 0.0265(12) Uani 1 1 d . . . . .
H31 H 0.204998 0.333983 0.773540 0.032 Uiso 1 1 calc R U . . .
C32 C 0.3154(10) 0.2443(5) 0.8593(4) 0.0388(15) Uani 1 1 d . . . . .
H32A H 0.446068 0.299191 0.869419 0.058 Uiso 1 1 calc R U . . .
H32B H 0.347303 0.172952 0.828439 0.058 Uiso 1 1 calc R U . . .
H32C H 0.259226 0.214095 0.904339 0.058 Uiso 1 1 calc R U . . .
C33 C -0.0623(9) 0.2405(5) 0.8120(3) 0.0324(13) Uani 1 1 d . . . . .
H33A H -0.115716 0.217601 0.858788 0.049 Uiso 1 1 calc R U . . .
H33B H -0.045857 0.164413 0.782766 0.049 Uiso 1 1 calc R U . . .
H33C H -0.163741 0.290669 0.787943 0.049 Uiso 1 1 calc R U . . .
C34 C 0.0529(8) 0.4398(5) 0.9340(3) 0.0240(12) Uani 1 1 d . . . . .
H34 H 0.026155 0.350344 0.946616 0.029 Uiso 1 1 calc R U . . .
C35 C -0.1601(8) 0.4963(5) 0.9386(3) 0.0319(13) Uani 1 1 d . . . . .
H35A H -0.147661 0.580123 0.919535 0.048 Uiso 1 1 calc R U . . .
H35B H -0.200755 0.501799 0.988730 0.048 Uiso 1 1 calc R U . . .
H35C H -0.269279 0.443198 0.910650 0.048 Uiso 1 1 calc R U . . .
C36 C 0.2253(9) 0.4981(5) 0.9868(3) 0.0302(13) Uani 1 1 d . . . . .
H36A H 0.349950 0.449312 0.985141 0.045 Uiso 1 1 calc R U . . .
H36B H 0.170459 0.498382 1.035250 0.045 Uiso 1 1 calc R U . . .
H36C H 0.266601 0.584209 0.974025 0.045 Uiso 1 1 calc R U . . .
C37 C 0.1074(8) 0.8048(5) 0.9178(3) 0.0223(11) Uani 1 1 d . . . . .
H37 H 0.090969 0.721546 0.940115 0.027 Uiso 1 1 calc R U . . .
C38 C -0.1101(9) 0.8559(5) 0.9163(3) 0.0293(13) Uani 1 1 d . . . . .
H38A H -0.098026 0.940059 0.897568 0.044 Uiso 1 1 calc R U . . .
H38B H -0.163374 0.859724 0.964940 0.044 Uiso 1 1 calc R U . . .
H38C H -0.209317 0.801001 0.885501 0.044 Uiso 1 1 calc R U . . .
C39 C 0.2706(8) 0.8867(5) 0.9631(3) 0.0292(13) Uani 1 1 d . . . . .
H39A H 0.406596 0.848523 0.963914 0.044 Uiso 1 1 calc R U . . .
H39B H 0.220687 0.895205 1.012041 0.044 Uiso 1 1 calc R U . . .
H39C H 0.290170 0.969479 0.942865 0.044 Uiso 1 1 calc R U . . .
C40 C 0.2192(8) 0.8931(4) 0.7991(3) 0.0211(11) Uani 1 1 d . . . . .
H40 H 0.191599 0.968535 0.829284 0.025 Uiso 1 1 calc R U . . .
C41 C 0.0592(9) 0.8860(5) 0.7364(3) 0.0305(13) Uani 1 1 d . . . . .
H41A H 0.082727 0.814247 0.704509 0.046 Uiso 1 1 calc R U . . .
H41B H 0.077302 0.963029 0.710058 0.046 Uiso 1 1 calc R U . . .
H41C H -0.085683 0.876065 0.754214 0.046 Uiso 1 1 calc R U . . .
C42 C 0.4487(9) 0.9120(5) 0.7773(3) 0.0306(13) Uani 1 1 d . . . . .
H42A H 0.542216 0.926085 0.820165 0.046 Uiso 1 1 calc R U . . .
H42B H 0.466238 0.984788 0.747337 0.046 Uiso 1 1 calc R U . . .
H42C H 0.486130 0.837461 0.750233 0.046 Uiso 1 1 calc R U . . .
C43 C 0.3956(8) 0.6657(4) 0.6337(2) 0.0186(10) Uani 1 1 d . . . . .
C44 C 0.2040(9) 0.6847(5) 0.5978(3) 0.0284(12) Uani 1 1 d . . . . .
H44 H 0.078461 0.634667 0.608705 0.034 Uiso 1 1 calc R U . . .
C45 C 0.1908(10) 0.7740(5) 0.5467(3) 0.0357(14) Uani 1 1 d . . . . .
H45 H 0.058520 0.783207 0.522474 0.043 Uiso 1 1 calc R U . . .
C46 C 0.3688(11) 0.8490(5) 0.5311(3) 0.0368(15) Uani 1 1 d . . . . .
H46 H 0.359252 0.911763 0.497002 0.044 Uiso 1 1 calc R U . . .
C47 C 0.5621(10) 0.8331(5) 0.5650(3) 0.0328(14) Uani 1 1 d . . . . .
H47 H 0.686195 0.884286 0.554016 0.039 Uiso 1 1 calc R U . . .
C48 C 0.5739(9) 0.7415(5) 0.6153(3) 0.0298(13) Uani 1 1 d . . . . .
H48 H 0.707998 0.730533 0.637743 0.036 Uiso 1 1 calc R U . . .
C49 C 0.3325(8) 0.4197(5) 0.6608(2) 0.0210(11) Uani 1 1 d . . . . .
C50 C 0.4751(9) 0.3267(5) 0.6540(3) 0.0297(13) Uani 1 1 d . . . . .
H50 H 0.621046 0.346984 0.667360 0.036 Uiso 1 1 calc R U . . .
C51 C 0.4096(10) 0.2052(5) 0.6282(3) 0.0338(14) Uani 1 1 d . . . . .
H51 H 0.509491 0.143818 0.625205 0.041 Uiso 1 1 calc R U . . .
C52 C 0.1986(10) 0.1749(5) 0.6069(3) 0.0374(15) Uani 1 1 d . . . . .
H52 H 0.153649 0.092966 0.588383 0.045 Uiso 1 1 calc R U . . .
C53 C 0.0528(10) 0.2645(5) 0.6127(3) 0.0329(14) Uani 1 1 d . . . . .
H53 H -0.092634 0.244219 0.598658 0.039 Uiso 1 1 calc R U . . .
C54 C 0.1214(9) 0.3837(5) 0.6392(3) 0.0272(12) Uani 1 1 d . . . . .
H54 H 0.019727 0.443978 0.642925 0.033 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
Cl1 B1 1.942(5) . ?
Cl2 B2 1.950(5) . ?
N1 C2 1.320(6) . ?
N1 C7 1.472(6) . ?
N1 C4 1.487(6) . ?
N2 C3 1.335(6) . ?
N2 C10 1.485(6) . ?
N2 C13 1.488(6) . ?
N3 C29 1.324(6) . ?
N3 C34 1.483(6) . ?
N3 C31 1.486(6) . ?
N4 C30 1.327(6) . ?
N4 C37 1.479(6) . ?
N4 C40 1.486(6) . ?
B1 C22 1.621(7) . ?
B1 C1 1.627(7) . ?
B1 C16 1.629(7) . ?
B2 C43 1.599(7) . ?
B2 C28 1.628(7) . ?
B2 C49 1.638(7) . ?
C1 C3 1.377(6) . ?
C1 C2 1.382(7) . ?
C2 C3 1.385(6) . ?
C4 C6 1.510(7) . ?
C4 C5 1.519(7) . ?
C4 H4 1.0000 . ?
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 C9 1.516(7) . ?
C7 C8 1.517(7) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.520(7) . ?
C10 C12 1.530(7) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.516(8) . ?
C13 C14 1.524(7) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.397(7) . ?
C16 C17 1.401(7) . ?
C17 C18 1.384(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.391(6) . ?
C22 C27 1.407(7) . ?
C23 C24 1.383(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.373(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(7) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.384(7) . ?
C28 C30 1.393(6) . ?
C29 C30 1.384(7) . ?
C31 C32 1.503(8) . ?
C31 C33 1.519(7) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.521(7) . ?
C34 C36 1.523(7) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C39 1.512(7) . ?
C37 C38 1.517(7) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C42 1.513(7) . ?
C40 C41 1.517(7) . ?
C40 H40 1.0000 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C48 1.392(7) . ?
C43 C44 1.397(7) . ?
C44 C45 1.386(7) . ?
C44 H44 0.9500 . ?
C45 C46 1.370(8) . ?
C45 H45 0.9500 . ?
C46 C47 1.382(8) . ?
C46 H46 0.9500 . ?
C47 C48 1.392(7) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C54 1.396(7) . ?
C49 C50 1.402(7) . ?
C50 C51 1.398(7) . ?
C50 H50 0.9500 . ?
C51 C52 1.384(8) . ?
C51 H51 0.9500 . ?
C52 C53 1.388(8) . ?
C52 H52 0.9500 . ?
C53 C54 1.384(7) . ?
C53 H53 0.9500 . ?
C54 H54 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
C2 N1 C7 121.3(4) . . ?
C2 N1 C4 121.0(4) . . ?
C7 N1 C4 117.7(4) . . ?
C3 N2 C10 122.4(4) . . ?
C3 N2 C13 117.7(4) . . ?
C10 N2 C13 119.7(4) . . ?
C29 N3 C34 123.5(4) . . ?
C29 N3 C31 117.5(4) . . ?
C34 N3 C31 119.0(4) . . ?
C30 N4 C37 121.1(4) . . ?
C30 N4 C40 120.3(4) . . ?
C37 N4 C40 118.4(4) . . ?
C22 B1 C1 113.1(4) . . ?
C22 B1 C16 112.4(4) . . ?
C1 B1 C16 111.2(4) . . ?
C22 B1 Cl1 109.5(3) . . ?
C1 B1 Cl1 100.3(3) . . ?
C16 B1 Cl1 109.5(3) . . ?
C43 B2 C28 115.0(4) . . ?
C43 B2 C49 113.6(4) . . ?
C28 B2 C49 109.3(4) . . ?
C43 B2 Cl2 109.9(3) . . ?
C28 B2 Cl2 99.5(3) . . ?
C49 B2 Cl2 108.4(3) . . ?
C3 C1 C2 60.3(3) . . ?
C3 C1 B1 145.8(4) . . ?
C2 C1 B1 151.4(4) . . ?
N1 C2 C1 150.6(5) . . ?
N1 C2 C3 149.6(5) . . ?
C1 C2 C3 59.7(3) . . ?
N2 C3 C1 146.5(5) . . ?
N2 C3 C2 153.4(4) . . ?
C1 C3 C2 60.0(3) . . ?
N1 C4 C6 111.6(4) . . ?
N1 C4 C5 111.1(4) . . ?
C6 C4 C5 113.0(4) . . ?
N1 C4 H4 106.9 . . ?
C6 C4 H4 106.9 . . ?
C5 C4 H4 106.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C9 111.6(4) . . ?
N1 C7 C8 111.9(4) . . ?
C9 C7 C8 112.6(4) . . ?
N1 C7 H7 106.8 . . ?
C9 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 112.1(4) . . ?
N2 C10 C12 110.2(4) . . ?
C11 C10 C12 115.5(4) . . ?
N2 C10 H10 106.1 . . ?
C11 C10 H10 106.1 . . ?
C12 C10 H10 106.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C15 110.6(4) . . ?
N2 C13 C14 110.6(4) . . ?
C15 C13 C14 112.3(5) . . ?
N2 C13 H13 107.7 . . ?
C15 C13 H13 107.7 . . ?
C14 C13 H13 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 116.2(5) . . ?
C21 C16 B1 123.9(4) . . ?
C17 C16 B1 119.9(4) . . ?
C18 C17 C16 122.4(5) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C19 120.2(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 119.0(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 120.3(5) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 121.9(5) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
C23 C22 C27 116.0(4) . . ?
C23 C22 B1 124.8(4) . . ?
C27 C22 B1 119.2(4) . . ?
C24 C23 C22 122.4(5) . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C23 C24 C25 120.4(5) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 118.8(5) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C27 120.7(5) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 121.7(5) . . ?
C26 C27 H27 119.1 . . ?
C22 C27 H27 119.1 . . ?
C29 C28 C30 59.8(3) . . ?
C29 C28 B2 145.4(4) . . ?
C30 C28 B2 151.5(4) . . ?
N3 C29 C30 153.4(5) . . ?
N3 C29 C28 146.1(5) . . ?
C30 C29 C28 60.5(3) . . ?
N4 C30 C29 150.1(5) . . ?
N4 C30 C28 150.1(5) . . ?
C29 C30 C28 59.8(3) . . ?
N3 C31 C32 111.2(4) . . ?
N3 C31 C33 111.4(4) . . ?
C32 C31 C33 112.2(5) . . ?
N3 C31 H31 107.3 . . ?
C32 C31 H31 107.3 . . ?
C33 C31 H31 107.3 . . ?
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 . . ?
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 . . ?
N3 C34 C35 112.0(4) . . ?
N3 C34 C36 110.7(4) . . ?
C35 C34 C36 114.6(4) . . ?
N3 C34 H34 106.3 . . ?
C35 C34 H34 106.3 . . ?
C36 C34 H34 106.3 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N4 C37 C39 110.9(4) . . ?
N4 C37 C38 111.4(4) . . ?
C39 C37 C38 112.4(4) . . ?
N4 C37 H37 107.3 . . ?
C39 C37 H37 107.3 . . ?
C38 C37 H37 107.3 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N4 C40 C42 111.7(4) . . ?
N4 C40 C41 111.3(4) . . ?
C42 C40 C41 113.6(4) . . ?
N4 C40 H40 106.6 . . ?
C42 C40 H40 106.6 . . ?
C41 C40 H40 106.6 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C48 C43 C44 116.3(5) . . ?
C48 C43 B2 123.9(5) . . ?
C44 C43 B2 119.9(4) . . ?
C45 C44 C43 122.2(5) . . ?
C45 C44 H44 118.9 . . ?
C43 C44 H44 118.9 . . ?
C46 C45 C44 119.9(6) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C47 119.9(5) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.1 . . ?
C46 C47 C48 119.6(5) . . ?
C46 C47 H47 120.2 . . ?
C48 C47 H47 120.2 . . ?
C43 C48 C47 122.1(5) . . ?
C43 C48 H48 119.0 . . ?
C47 C48 H48 119.0 . . ?
C54 C49 C50 115.7(5) . . ?
C54 C49 B2 120.3(4) . . ?
C50 C49 B2 124.0(5) . . ?
C51 C50 C49 122.1(5) . . ?
C51 C50 H50 118.9 . . ?
C49 C50 H50 118.9 . . ?
C52 C51 C50 119.7(5) . . ?
C52 C51 H51 120.2 . . ?
C50 C51 H51 120.2 . . ?
C51 C52 C53 119.8(5) . . ?
C51 C52 H52 120.1 . . ?
C53 C52 H52 120.1 . . ?
C54 C53 C52 119.3(6) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
C53 C54 C49 123.3(5) . . ?
C53 C54 H54 118.4 . . ?
C49 C54 H54 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 B1 C1 C3 -163.3(6) . . . . ?
C16 B1 C1 C3 -35.6(9) . . . . ?
Cl1 B1 C1 C3 80.2(8) . . . . ?
C22 B1 C1 C2 47.4(10) . . . . ?
C16 B1 C1 C2 175.1(8) . . . . ?
Cl1 B1 C1 C2 -69.1(9) . . . . ?
C7 N1 C2 C1 173.6(8) . . . . ?
C4 N1 C2 C1 -9.0(11) . . . . ?
C7 N1 C2 C3 -1.6(11) . . . . ?
C4 N1 C2 C3 175.9(7) . . . . ?
C3 C1 C2 N1 -177.2(10) . . . . ?
B1 C1 C2 N1 -16.5(15) . . . . ?
B1 C1 C2 C3 160.7(9) . . . . ?
C10 N2 C3 C1 -179.1(7) . . . . ?
C13 N2 C3 C1 6.3(10) . . . . ?
C10 N2 C3 C2 -0.1(13) . . . . ?
C13 N2 C3 C2 -174.6(9) . . . . ?
C2 C1 C3 N2 179.5(9) . . . . ?
B1 C1 C3 N2 15.8(13) . . . . ?
B1 C1 C3 C2 -163.7(8) . . . . ?
N1 C2 C3 N2 -2.1(17) . . . . ?
C1 C2 C3 N2 -179.4(11) . . . . ?
N1 C2 C3 C1 177.2(9) . . . . ?
C2 N1 C4 C6 60.4(6) . . . . ?
C7 N1 C4 C6 -122.0(5) . . . . ?
C2 N1 C4 C5 -66.7(6) . . . . ?
C7 N1 C4 C5 110.8(5) . . . . ?
C2 N1 C7 C9 -118.4(5) . . . . ?
C4 N1 C7 C9 64.1(6) . . . . ?
C2 N1 C7 C8 114.4(5) . . . . ?
C4 N1 C7 C8 -63.1(6) . . . . ?
C3 N2 C10 C11 -61.6(6) . . . . ?
C13 N2 C10 C11 112.9(5) . . . . ?
C3 N2 C10 C12 68.5(6) . . . . ?
C13 N2 C10 C12 -117.0(5) . . . . ?
C3 N2 C13 C15 112.5(5) . . . . ?
C10 N2 C13 C15 -62.2(6) . . . . ?
C3 N2 C13 C14 -122.5(5) . . . . ?
C10 N2 C13 C14 62.8(6) . . . . ?
C22 B1 C16 C21 -114.0(5) . . . . ?
C1 B1 C16 C21 117.9(5) . . . . ?
Cl1 B1 C16 C21 8.0(6) . . . . ?
C22 B1 C16 C17 66.4(6) . . . . ?
C1 B1 C16 C17 -61.7(6) . . . . ?
Cl1 B1 C16 C17 -171.7(4) . . . . ?
C21 C16 C17 C18 -0.3(7) . . . . ?
B1 C16 C17 C18 179.4(5) . . . . ?
C16 C17 C18 C19 -0.5(8) . . . . ?
C17 C18 C19 C20 0.3(8) . . . . ?
C18 C19 C20 C21 0.7(8) . . . . ?
C19 C20 C21 C16 -1.5(8) . . . . ?
C17 C16 C21 C20 1.3(7) . . . . ?
B1 C16 C21 C20 -178.3(5) . . . . ?
C1 B1 C22 C23 -121.1(5) . . . . ?
C16 B1 C22 C23 111.9(5) . . . . ?
Cl1 B1 C22 C23 -10.1(6) . . . . ?
C1 B1 C22 C27 59.6(6) . . . . ?
C16 B1 C22 C27 -67.5(5) . . . . ?
Cl1 B1 C22 C27 170.5(4) . . . . ?
C27 C22 C23 C24 -0.2(7) . . . . ?
B1 C22 C23 C24 -179.6(5) . . . . ?
C22 C23 C24 C25 0.0(8) . . . . ?
C23 C24 C25 C26 0.3(8) . . . . ?
C24 C25 C26 C27 -0.3(8) . . . . ?
C25 C26 C27 C22 0.0(8) . . . . ?
C23 C22 C27 C26 0.3(7) . . . . ?
B1 C22 C27 C26 179.7(4) . . . . ?
C43 B2 C28 C29 170.1(6) . . . . ?
C49 B2 C28 C29 41.0(9) . . . . ?
Cl2 B2 C28 C29 -72.5(8) . . . . ?
C43 B2 C28 C30 -45.8(10) . . . . ?
C49 B2 C28 C30 -174.9(8) . . . . ?
Cl2 B2 C28 C30 71.6(9) . . . . ?
C34 N3 C29 C30 -3.4(13) . . . . ?
C31 N3 C29 C30 175.9(9) . . . . ?
C34 N3 C29 C28 176.8(7) . . . . ?
C31 N3 C29 C28 -3.9(10) . . . . ?
C30 C28 C29 N3 179.9(9) . . . . ?
B2 C28 C29 N3 -19.0(13) . . . . ?
B2 C28 C29 C30 161.1(8) . . . . ?
C37 N4 C30 C29 0.4(11) . . . . ?
C40 N4 C30 C29 -173.7(8) . . . . ?
C37 N4 C30 C28 -175.6(8) . . . . ?
C40 N4 C30 C28 10.3(11) . . . . ?
N3 C29 C30 N4 2.4(17) . . . . ?
C28 C29 C30 N4 -177.7(10) . . . . ?
N3 C29 C30 C28 -179.9(11) . . . . ?
C29 C28 C30 N4 177.7(10) . . . . ?
B2 C28 C30 N4 20.4(15) . . . . ?
B2 C28 C30 C29 -157.3(9) . . . . ?
C29 N3 C31 C32 116.9(5) . . . . ?
C34 N3 C31 C32 -63.8(6) . . . . ?
C29 N3 C31 C33 -117.2(5) . . . . ?
C34 N3 C31 C33 62.2(6) . . . . ?
C29 N3 C34 C35 64.0(6) . . . . ?
C31 N3 C34 C35 -115.3(5) . . . . ?
C29 N3 C34 C36 -65.3(6) . . . . ?
C31 N3 C34 C36 115.4(5) . . . . ?
C30 N4 C37 C39 121.9(5) . . . . ?
C40 N4 C37 C39 -63.8(5) . . . . ?
C30 N4 C37 C38 -112.1(5) . . . . ?
C40 N4 C37 C38 62.2(5) . . . . ?
C30 N4 C40 C42 -66.0(6) . . . . ?
C37 N4 C40 C42 119.7(5) . . . . ?
C30 N4 C40 C41 62.1(6) . . . . ?
C37 N4 C40 C41 -112.2(5) . . . . ?
C28 B2 C43 C48 114.7(5) . . . . ?
C49 B2 C43 C48 -118.4(5) . . . . ?
Cl2 B2 C43 C48 3.4(6) . . . . ?
C28 B2 C43 C44 -64.7(6) . . . . ?
C49 B2 C43 C44 62.2(6) . . . . ?
Cl2 B2 C43 C44 -176.0(4) . . . . ?
C48 C43 C44 C45 -0.1(7) . . . . ?
B2 C43 C44 C45 179.4(5) . . . . ?
C43 C44 C45 C46 -1.4(8) . . . . ?
C44 C45 C46 C47 1.7(8) . . . . ?
C45 C46 C47 C48 -0.6(8) . . . . ?
C44 C43 C48 C47 1.2(7) . . . . ?
B2 C43 C48 C47 -178.2(5) . . . . ?
C46 C47 C48 C43 -0.9(8) . . . . ?
C43 B2 C49 C54 -70.7(6) . . . . ?
C28 B2 C49 C54 59.1(6) . . . . ?
Cl2 B2 C49 C54 166.7(4) . . . . ?
C43 B2 C49 C50 110.1(5) . . . . ?
C28 B2 C49 C50 -120.0(5) . . . . ?
Cl2 B2 C49 C50 -12.4(6) . . . . ?
C54 C49 C50 C51 -0.8(7) . . . . ?
B2 C49 C50 C51 178.3(5) . . . . ?
C49 C50 C51 C52 1.5(8) . . . . ?
C50 C51 C52 C53 -1.3(8) . . . . ?
C51 C52 C53 C54 0.6(8) . . . . ?
C52 C53 C54 C49 0.0(8) . . . . ?
C50 C49 C54 C53 0.1(7) . . . . ?
B2 C49 C54 C53 -179.1(5) . . . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_AS003_cmpd23
_database_code_depnum_ccdc_archive 'CCDC 1914230'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2019-06-04 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H38 B F N2'
_chemical_formula_sum            'C27 H38 B F N2'
_chemical_formula_weight         420.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   17.3954(17)
_cell_length_b                   9.9115(10)
_cell_length_c                   14.4462(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2490.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.84

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7074
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28896
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         28.960
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6214
_reflns_number_gt                5876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.999

_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    'SHELXT-2014 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0483P)²+0.3373P] 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 2650 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6214
_refine_ls_number_parameters     352
_refine_ls_number_restraints     250
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.037
_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
F1 F 0.25808(5) 0.45393(9) 0.36111(7) 0.0264(2) Uani 1 1 d . . . . .
N1 N 0.43000(8) 0.43909(13) 0.53687(9) 0.0237(3) Uani 1 1 d . . . . .
B1 B 0.25213(9) 0.58564(17) 0.40451(12) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.30761(8) 0.58094(14) 0.49652(10) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.37181(8) 0.52541(15) 0.53930(10) 0.0199(3) Uani 1 1 d . . . . .
C3 C 0.33149(9) 0.62958(15) 0.58207(10) 0.0219(3) Uani 1 1 d D . . . .
C4 C 0.43426(9) 0.33870(16) 0.46047(12) 0.0253(3) Uani 1 1 d . . . . .
H4 H 0.482235 0.284939 0.470129 0.030 Uiso 1 1 calc R U . . .
C5 C 0.44214(10) 0.40971(18) 0.36762(12) 0.0306(4) Uani 1 1 d . . . . .
H5A H 0.397287 0.467618 0.357301 0.046 Uiso 1 1 calc R U . . .
H5B H 0.445348 0.342344 0.318117 0.046 Uiso 1 1 calc R U . . .
H5C H 0.488872 0.464940 0.367617 0.046 Uiso 1 1 calc R U . . .
C6 C 0.36712(11) 0.24007(17) 0.46313(14) 0.0337(4) Uani 1 1 d . . . . .
H6A H 0.365894 0.194735 0.523399 0.051 Uiso 1 1 calc R U . . .
H6B H 0.373386 0.172753 0.414023 0.051 Uiso 1 1 calc R U . . .
H6C H 0.318892 0.289290 0.453686 0.051 Uiso 1 1 calc R U . . .
C7 C 0.48379(10) 0.42921(17) 0.61664(12) 0.0288(4) Uani 1 1 d . . . . .
H7 H 0.481803 0.517533 0.650007 0.035 Uiso 1 1 calc R U . . .
C8 C 0.56681(10) 0.4078(2) 0.58616(15) 0.0391(4) Uani 1 1 d . . . . .
H8A H 0.572658 0.316361 0.561253 0.059 Uiso 1 1 calc R U . . .
H8B H 0.601085 0.419353 0.639400 0.059 Uiso 1 1 calc R U . . .
H8C H 0.580033 0.473766 0.538229 0.059 Uiso 1 1 calc R U . . .
C9 C 0.45855(11) 0.3217(3) 0.68452(14) 0.0469(5) Uani 1 1 d . . . . .
H9A H 0.406473 0.341874 0.706386 0.070 Uiso 1 1 calc R U . . .
H9B H 0.493941 0.320086 0.737293 0.070 Uiso 1 1 calc R U . . .
H9C H 0.458892 0.233504 0.653854 0.070 Uiso 1 1 calc R U . . .
N2A N 0.32541(12) 0.7150(2) 0.65225(15) 0.0280(4) Uani 0.881(3) 1 d D U P A 1
C10A C 0.37617(15) 0.7051(3) 0.73479(14) 0.0377(6) Uani 0.881(3) 1 d D U P A 1
H10A H 0.415845 0.634933 0.720869 0.045 Uiso 0.881(3) 1 calc R U P A 1
C11A C 0.33142(18) 0.6566(3) 0.81902(18) 0.0455(7) Uani 0.881(3) 1 d D U P A 1
H11A H 0.292959 0.724498 0.836035 0.068 Uiso 0.881(3) 1 calc R U P A 1
H11B H 0.366872 0.642880 0.870888 0.068 Uiso 0.881(3) 1 calc R U P A 1
H11C H 0.305626 0.571385 0.804353 0.068 Uiso 0.881(3) 1 calc R U P A 1
C12A C 0.41844(15) 0.8362(4) 0.75193(19) 0.0472(7) Uani 0.881(3) 1 d D U P A 1
H12A H 0.381309 0.907293 0.766821 0.071 Uiso 0.881(3) 1 calc R U P A 1
H12B H 0.447241 0.861415 0.696265 0.071 Uiso 0.881(3) 1 calc R U P A 1
H12C H 0.454139 0.824686 0.803819 0.071 Uiso 0.881(3) 1 calc R U P A 1
C13A C 0.26291(11) 0.81841(19) 0.65388(15) 0.0254(4) Uani 0.881(3) 1 d D U P A
1
H13A H 0.271303 0.875625 0.709986 0.030 Uiso 0.881(3) 1 calc R U P A 1
C14A C 0.18408(15) 0.7530(3) 0.66392(19) 0.0283(5) Uani 0.881(3) 1 d D U P A 1
H14A H 0.174310 0.694402 0.610573 0.042 Uiso 0.881(3) 1 calc R U P A 1
H14B H 0.144536 0.823336 0.666798 0.042 Uiso 0.881(3) 1 calc R U P A 1
H14C H 0.182677 0.699302 0.720841 0.042 Uiso 0.881(3) 1 calc R U P A 1
C15A C 0.26866(11) 0.9103(2) 0.57024(17) 0.0285(4) Uani 0.881(3) 1 d D U P A 1
H15A H 0.320424 0.949060 0.567069 0.043 Uiso 0.881(3) 1 calc R U P A 1
H15B H 0.230775 0.983054 0.575710 0.043 Uiso 0.881(3) 1 calc R U P A 1
H15C H 0.258502 0.858213 0.513898 0.043 Uiso 0.881(3) 1 calc R U P A 1
N2B N 0.3041(10) 0.721(2) 0.6428(12) 0.0300(18) Uani 0.119(3) 1 d D U P A 2
C10B C 0.3410(10) 0.7332(16) 0.7310(9) 0.0332(17) Uani 0.119(3) 1 d D U P A 2
H10B H 0.311636 0.804366 0.764899 0.040 Uiso 0.119(3) 1 calc R U P A 2
C11B C 0.3358(12) 0.6083(18) 0.7907(13) 0.038(3) Uani 0.119(3) 1 d D U P A 2
H11D H 0.362255 0.624480 0.849528 0.057 Uiso 0.119(3) 1 calc R U P A 2
H11E H 0.281693 0.587146 0.802568 0.057 Uiso 0.119(3) 1 calc R U P A 2
H11F H 0.360146 0.532371 0.758578 0.057 Uiso 0.119(3) 1 calc R U P A 2
C12B C 0.4218(9) 0.787(2) 0.7225(14) 0.039(3) Uani 0.119(3) 1 d D U P A 2
H12D H 0.444967 0.793829 0.784124 0.058 Uiso 0.119(3) 1 calc R U P A 2
H12E H 0.452465 0.725480 0.684167 0.058 Uiso 0.119(3) 1 calc R U P A 2
H12F H 0.420577 0.876316 0.693534 0.058 Uiso 0.119(3) 1 calc R U P A 2
C13B C 0.2414(8) 0.8109(13) 0.6116(11) 0.0276(18) Uani 0.119(3) 1 d D U P A 2
H13B H 0.226626 0.785036 0.547098 0.033 Uiso 0.119(3) 1 calc R U P A 2
C14B C 0.1712(10) 0.793(2) 0.6745(16) 0.031(3) Uani 0.119(3) 1 d D U P A 2
H14D H 0.129813 0.853104 0.653609 0.046 Uiso 0.119(3) 1 calc R U P A 2
H14E H 0.153602 0.699414 0.671842 0.046 Uiso 0.119(3) 1 calc R U P A 2
H14F H 0.185187 0.816046 0.738340 0.046 Uiso 0.119(3) 1 calc R U P A 2
C15B C 0.2695(10) 0.9561(15) 0.6108(15) 0.038(3) Uani 0.119(3) 1 d D U P A 2
H15D H 0.227859 1.015447 0.590126 0.057 Uiso 0.119(3) 1 calc R U P A 2
H15E H 0.285511 0.982037 0.673355 0.057 Uiso 0.119(3) 1 calc R U P A 2
H15F H 0.313237 0.964293 0.568431 0.057 Uiso 0.119(3) 1 calc R U P A 2
C16 C 0.16280(8) 0.60657(16) 0.43463(10) 0.0207(3) Uani 1 1 d . . . . .
C17 C 0.12288(9) 0.49842(17) 0.47472(11) 0.0263(3) Uani 1 1 d . . . . .
H17 H 0.148066 0.413833 0.480752 0.032 Uiso 1 1 calc R U . . .
C18 C 0.04768(10) 0.5110(2) 0.50590(14) 0.0336(4) Uani 1 1 d . . . . .
H18 H 0.022616 0.436168 0.533733 0.040 Uiso 1 1 calc R U . . .
C19 C 0.00927(9) 0.6323(2) 0.49649(13) 0.0347(4) Uani 1 1 d . . . . .
H19 H -0.042041 0.641366 0.518122 0.042 Uiso 1 1 calc R U . . .
C20 C 0.04616(9) 0.74030(19) 0.45532(13) 0.0320(4) Uani 1 1 d . . . . .
H20 H 0.019841 0.823543 0.447694 0.038 Uiso 1 1 calc R U . . .
C21 C 0.12203(9) 0.72731(16) 0.42491(12) 0.0252(3) Uani 1 1 d . . . . .
H21 H 0.146585 0.802543 0.396874 0.030 Uiso 1 1 calc R U . . .
C22 C 0.28364(9) 0.69899(16) 0.33321(11) 0.0222(3) Uani 1 1 d . . . . .
C23 C 0.34560(10) 0.78357(18) 0.35021(12) 0.0308(4) Uani 1 1 d . . . . .
H23 H 0.371835 0.776250 0.407667 0.037 Uiso 1 1 calc R U . . .
C24 C 0.37076(13) 0.8789(2) 0.28609(15) 0.0404(5) Uani 1 1 d . . . . .
H24 H 0.413391 0.935192 0.300088 0.049 Uiso 1 1 calc R U . . .
C25 C 0.33350(13) 0.8911(2) 0.20219(15) 0.0419(5) Uani 1 1 d . . . . .
H25 H 0.349627 0.957122 0.158634 0.050 Uiso 1 1 calc R U . . .
C26 C 0.27232(12) 0.8064(2) 0.18189(14) 0.0425(5) Uani 1 1 d . . . . .
H26 H 0.247094 0.812946 0.123742 0.051 Uiso 1 1 calc R U . . .
C27 C 0.24792(10) 0.7119(2) 0.24650(12) 0.0342(4) Uani 1 1 d . . . . .
H27 H 0.205945 0.654563 0.231655 0.041 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
F1 B1 1.4520(19) . ?
N1 C2 1.3258(19) . ?
N1 C7 1.488(2) . ?
N1 C4 1.4879(19) . ?
B1 C22 1.620(2) . ?
B1 C16 1.627(2) . ?
B1 C1 1.643(2) . ?
C1 C2 1.390(2) . ?
C1 C3 1.390(2) . ?
C2 C3 1.393(2) . ?
C3 N2A 1.325(3) . ?
C3 N2B 1.347(16) . ?
C4 C5 1.521(2) . ?
C4 C6 1.523(2) . ?
C4 H4 1.0000 . ?
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 C9 1.513(3) . ?
C7 C8 1.525(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N2A C10A 1.487(3) . ?
N2A C13A 1.494(2) . ?
C10A C12A 1.513(4) . ?
C10A C11A 1.522(4) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A C15A 1.516(3) . ?
C13A C14A 1.524(3) . ?
C13A H13A 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
N2B C10B 1.431(17) . ?
N2B C13B 1.481(17) . ?
C10B C12B 1.508(14) . ?
C10B C11B 1.511(14) . ?
C10B H10B 1.0000 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B C15B 1.519(14) . ?
C13B C14B 1.533(14) . ?
C13B H13B 1.0000 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16 C21 1.398(2) . ?
C16 C17 1.402(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.397(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 C27 1.404(2) . ?
C23 C24 1.393(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(3) . ?
C26 H26 0.9500 . ?
C27 H27 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
C2 N1 C7 120.15(13) . . ?
C2 N1 C4 119.29(12) . . ?
C7 N1 C4 119.95(12) . . ?
F1 B1 C22 108.96(12) . . ?
F1 B1 C16 107.35(12) . . ?
C22 B1 C16 113.88(12) . . ?
F1 B1 C1 106.38(12) . . ?
C22 B1 C1 109.60(12) . . ?
C16 B1 C1 110.38(12) . . ?
C2 C1 C3 60.13(11) . . ?
C2 C1 B1 147.43(13) . . ?
C3 C1 B1 152.23(13) . . ?
N1 C2 C1 149.00(14) . . ?
N1 C2 C3 150.99(14) . . ?
C1 C2 C3 59.94(11) . . ?
N2A C3 C1 151.39(16) . . ?
N2B C3 C1 135.0(6) . . ?
N2A C3 C2 148.58(16) . . ?
N2B C3 C2 164.7(7) . . ?
C1 C3 C2 59.93(10) . . ?
N1 C4 C5 110.44(13) . . ?
N1 C4 C6 111.85(14) . . ?
C5 C4 C6 112.85(14) . . ?
N1 C4 H4 107.1 . . ?
C5 C4 H4 107.1 . . ?
C6 C4 H4 107.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C9 111.46(15) . . ?
N1 C7 C8 112.41(15) . . ?
C9 C7 C8 111.33(15) . . ?
N1 C7 H7 107.1 . . ?
C9 C7 H7 107.1 . . ?
C8 C7 H7 107.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 N2A C10A 121.59(17) . . ?
C3 N2A C13A 120.56(17) . . ?
C10A N2A C13A 117.69(18) . . ?
N2A C10A C12A 111.3(2) . . ?
N2A C10A C11A 111.0(2) . . ?
C12A C10A C11A 112.9(2) . . ?
N2A C10A H10A 107.1 . . ?
C12A C10A H10A 107.1 . . ?
C11A C10A H10A 107.1 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N2A C13A C15A 110.57(17) . . ?
N2A C13A C14A 111.38(18) . . ?
C15A C13A C14A 113.00(19) . . ?
N2A C13A H13A 107.2 . . ?
C15A C13A H13A 107.2 . . ?
C14A C13A H13A 107.2 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C3 N2B C10B 118.6(12) . . ?
C3 N2B C13B 117.8(12) . . ?
C10B N2B C13B 123.3(14) . . ?
N2B C10B C12B 112.1(14) . . ?
N2B C10B C11B 114.2(14) . . ?
C12B C10B C11B 113.1(15) . . ?
N2B C10B H10B 105.5 . . ?
C12B C10B H10B 105.5 . . ?
C11B C10B H10B 105.5 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
N2B C13B C15B 109.7(14) . . ?
N2B C13B C14B 109.8(14) . . ?
C15B C13B C14B 111.6(14) . . ?
N2B C13B H13B 108.6 . . ?
C15B C13B H13B 108.6 . . ?
C14B C13B H13B 108.6 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C13B C15B H15D 109.5 . . ?
C13B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C21 C16 C17 116.39(14) . . ?
C21 C16 B1 124.52(14) . . ?
C17 C16 B1 119.08(13) . . ?
C18 C17 C16 122.10(15) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C19 C18 C17 120.12(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.43(16) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 120.16(16) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 121.77(15) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
C23 C22 C27 116.52(15) . . ?
C23 C22 B1 124.71(14) . . ?
C27 C22 B1 118.75(15) . . ?
C22 C23 C24 122.41(18) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C25 C24 C23 119.7(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.52(18) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 120.05(18) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 121.74(18) . . ?
C26 C27 H27 119.1 . . ?
C22 C27 H27 119.1 . . ?

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
F1 B1 C1 C2 27.3(3) . . . . ?
C22 B1 C1 C2 -90.3(3) . . . . ?
C16 B1 C1 C2 143.5(2) . . . . ?
F1 B1 C1 C3 -161.9(3) . . . . ?
C22 B1 C1 C3 80.4(3) . . . . ?
C16 B1 C1 C3 -45.8(3) . . . . ?
C7 N1 C2 C1 -179.5(2) . . . . ?
C4 N1 C2 C1 -8.5(4) . . . . ?
C7 N1 C2 C3 5.5(4) . . . . ?
C4 N1 C2 C3 176.5(3) . . . . ?
C3 C1 C2 N1 -177.2(3) . . . . ?
B1 C1 C2 N1 -2.2(5) . . . . ?
B1 C1 C2 C3 175.0(3) . . . . ?
C2 C1 C3 N2A 176.2(4) . . . . ?
B1 C1 C3 N2A 2.0(6) . . . . ?
C2 C1 C3 N2B -175.6(14) . . . . ?
B1 C1 C3 N2B 10.2(15) . . . . ?
B1 C1 C3 C2 -174.3(3) . . . . ?
N1 C2 C3 N2A 0.5(6) . . . . ?
C1 C2 C3 N2A -176.5(4) . . . . ?
N1 C2 C3 N2B -15(4) . . . . ?
C1 C2 C3 N2B 168(4) . . . . ?
N1 C2 C3 C1 177.0(3) . . . . ?
C2 N1 C4 C5 62.51(19) . . . . ?
C7 N1 C4 C5 -126.46(16) . . . . ?
C2 N1 C4 C6 -64.1(2) . . . . ?
C7 N1 C4 C6 106.96(17) . . . . ?
C2 N1 C7 C9 92.28(19) . . . . ?
C4 N1 C7 C9 -78.7(2) . . . . ?
C2 N1 C7 C8 -141.92(16) . . . . ?
C4 N1 C7 C8 47.1(2) . . . . ?
C1 C3 N2A C10A 177.8(3) . . . . ?
C2 C3 N2A C10A -8.4(5) . . . . ?
C1 C3 N2A C13A 2.5(5) . . . . ?
C2 C3 N2A C13A 176.3(2) . . . . ?
C3 N2A C10A C12A 124.1(3) . . . . ?
C13A N2A C10A C12A -60.5(3) . . . . ?
C3 N2A C10A C11A -109.3(3) . . . . ?
C13A N2A C10A C11A 66.1(3) . . . . ?
C3 N2A C13A C15A -59.5(3) . . . . ?
C10A N2A C13A C15A 125.1(2) . . . . ?
C3 N2A C13A C14A 67.1(3) . . . . ?
C10A N2A C13A C14A -108.4(3) . . . . ?
C1 C3 N2B C10B 172.8(9) . . . . ?
C2 C3 N2B C10B 8(5) . . . . ?
C1 C3 N2B C13B -12(3) . . . . ?
C2 C3 N2B C13B -178(2) . . . . ?
C3 N2B C10B C12B 66(2) . . . . ?
C13B N2B C10B C12B -108(2) . . . . ?
C3 N2B C10B C11B -64(2) . . . . ?
C13B N2B C10B C11B 122(2) . . . . ?
C3 N2B C13B C15B -115.6(19) . . . . ?
C10B N2B C13B C15B 59(2) . . . . ?
C3 N2B C13B C14B 121.4(19) . . . . ?
C10B N2B C13B C14B -64(2) . . . . ?
F1 B1 C16 C21 -138.98(15) . . . . ?
C22 B1 C16 C21 -18.3(2) . . . . ?
C1 B1 C16 C21 105.48(17) . . . . ?
F1 B1 C16 C17 42.15(18) . . . . ?
C22 B1 C16 C17 162.85(14) . . . . ?
C1 B1 C16 C17 -73.39(17) . . . . ?
C21 C16 C17 C18 -2.0(2) . . . . ?
B1 C16 C17 C18 177.01(15) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C17 C16 C21 C20 1.3(2) . . . . ?
B1 C16 C21 C20 -177.57(15) . . . . ?
F1 B1 C22 C23 -119.21(16) . . . . ?
C16 B1 C22 C23 121.00(16) . . . . ?
C1 B1 C22 C23 -3.2(2) . . . . ?
F1 B1 C22 C27 58.94(18) . . . . ?
C16 B1 C22 C27 -60.85(19) . . . . ?
C1 B1 C22 C27 174.96(14) . . . . ?
C27 C22 C23 C24 1.3(3) . . . . ?
B1 C22 C23 C24 179.50(16) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 -1.3(3) . . . . ?
C24 C25 C26 C27 1.3(3) . . . . ?
C25 C26 C27 C22 0.0(3) . . . . ?
C23 C22 C27 C26 -1.3(3) . . . . ?
B1 C22 C27 C26 -179.59(17) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.030

