# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_rds649
_database_code_depnum_ccdc_archive 'CCDC 1900105'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;NCSU
United States of America
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            BBu2-HDHDP
_chemical_formula_moiety         'C23 H37 B N2 O2'
_chemical_formula_sum            'C23 H37 B N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         384.35

_chemical_melting_point          391-393

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.8186(2)
_cell_length_b                   9.1192(2)
_cell_length_c                   22.4535(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.9509(8)
_cell_angle_gamma                90
_cell_volume                     2348.57(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    281
_cell_measurement_theta_min      1.9079
_cell_measurement_theta_max      22.6947
_cell_measurement_temperature    180.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.232
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840

_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
Crystals shatter when cooled to 100K for data collection. Diffraction very weak
for size and optical quality of crystal.
;

_diffrn_ambient_temperature      180.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            32991
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         23.82
_diffrn_reflns_theta_full        23.82
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
First pyrole ring (C1-C3 and attached C10-C12) is disordered over two
positions, indicating some puckering to the ring system.
n-butyl groups on B are also disordered over two positions. SAME and SADI
restraints used extensively to make reasonable and consistent bond lengths and
angles.

;

_reflns_number_total             3604
_reflns_number_gt                2926
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1252
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         3604
_refine_ls_number_parameters     392
_refine_ls_number_restraints     373
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.6055P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.48825(14) 1.0403(2) 0.22351(6) 0.1017(5) Uani d U . . 1.0 . .
O O2 0.29440(14) 1.00551(17) 0.20483(6) 0.0864(4) Uani d U . . 1.0 . .
N N1 0.29087(10) 0.70576(14) -0.06450(6) 0.0515(3) Uani d U . . 1.0 . .
N N2 0.31132(10) 0.82079(14) 0.04034(6) 0.0508(3) Uani d U . . 1.0 . .
C C1 0.2517(7) 0.6521(15) -0.1191(4) 0.0587(19) Uani d U P D 0.679(11) A 1
C C2 0.3459(7) 0.6077(8) -0.1507(3) 0.0669(16) Uani d U P D 0.679(11) A 1
C C3 0.4491(5) 0.6943(7) -0.1131(3) 0.0707(13) Uani d U P D 0.679(11) A 1
H H3A 0.5214 0.635 -0.1049 0.085 Uiso calc U P R 0.679(11) A 1
H H3B 0.4616 0.7855 -0.1345 0.085 Uiso calc U P R 0.679(11) A 1
C C10 0.1262(7) 0.6290(12) -0.1486(5) 0.078(2) Uani d U P D 0.679(11) A 1
H H10A 0.0825 0.6194 -0.1168 0.117 Uiso calc U P R 0.679(11) A 1
H H10B 0.117 0.5393 -0.1734 0.117 Uiso calc U P R 0.679(11) A 1
H H10C 0.0963 0.7129 -0.175 0.117 Uiso calc U P R 0.679(11) A 1
C C11 0.3655(6) 0.4418(5) -0.1450(3) 0.0944(16) Uani d U P D 0.679(11) A 1
H H11A 0.3886 0.4147 -0.1015 0.142 Uiso calc U P R 0.679(11) A 1
H H11B 0.4271 0.4137 -0.1651 0.142 Uiso calc U P R 0.679(11) A 1
H H11C 0.2931 0.3908 -0.1647 0.142 Uiso calc U P R 0.679(11) A 1
C C12 0.3130(6) 0.6530(10) -0.2180(2) 0.1105(19) Uani d U P D 0.679(11) A 1
H H12A 0.2447 0.5969 -0.2397 0.166 Uiso calc U P R 0.679(11) A 1
H H12B 0.3785 0.6332 -0.2366 0.166 Uiso calc U P R 0.679(11) A 1
H H12C 0.2947 0.7579 -0.2211 0.166 Uiso calc U P R 0.679(11) A 1
C C1A 0.2441(15) 0.635(3) -0.1149(10) 0.056(3) Uani d U P D 0.321(11) A 2
C C2A 0.3303(14) 0.6235(17) -0.1547(7) 0.075(4) Uani d U P D 0.321(11) A 2
C C3A 0.4465(12) 0.644(2) -0.1075(7) 0.095(5) Uani d U P D 0.321(11) A 2
H H3AA 0.5019 0.701 -0.125 0.114 Uiso calc U P R 0.321(11) A 2
H H3AB 0.4821 0.5478 -0.0932 0.114 Uiso calc U P R 0.321(11) A 2
C C10A 0.1204(15) 0.586(2) -0.1352(10) 0.072(4) Uani d U P D 0.321(11) A 2
H H10D 0.1095 0.4962 -0.1135 0.108 Uiso calc U P R 0.321(11) A 2
H H10E 0.1012 0.5676 -0.1795 0.108 Uiso calc U P R 0.321(11) A 2
H H10F 0.0692 0.6632 -0.126 0.108 Uiso calc U P R 0.321(11) A 2
C C11A 0.3273(11) 0.4691(14) -0.1815(8) 0.106(4) Uani d U P D 0.321(11) A 2
H H11D 0.3228 0.3969 -0.1497 0.159 Uiso calc U P R 0.321(11) A 2
H H11E 0.3983 0.4522 -0.1958 0.159 Uiso calc U P R 0.321(11) A 2
H H11F 0.2589 0.459 -0.216 0.159 Uiso calc U P R 0.321(11) A 2
C C12A 0.3095(15) 0.7367(17) -0.2069(6) 0.120(4) Uani d U P D 0.321(11) A 2
H H12D 0.2366 0.7138 -0.2369 0.18 Uiso calc U P R 0.321(11) A 2
H H12E 0.3744 0.7336 -0.227 0.18 Uiso calc U P R 0.321(11) A 2
H H12F 0.3043 0.835 -0.1901 0.18 Uiso calc U P R 0.321(11) A 2
C C4 0.41384(14) 0.7277(2) -0.05477(8) 0.0615(5) Uani d U . . 1.0 . .
C C5 0.47653(14) 0.7860(2) -0.00326(9) 0.0683(5) Uani d U . . 1.0 . .
H H5 0.558 0.7968 0.001 0.082 Uiso calc U . R 1.0 . .
C C6 0.42949(13) 0.83354(18) 0.04613(8) 0.0557(4) Uani d U . . 1.0 . .
C C7 0.47930(15) 0.8964(2) 0.10198(8) 0.0648(5) Uani d U . . 1.0 . .
H H7 0.5597 0.9175 0.1177 0.078 Uiso calc U . R 1.0 . .
C C8 0.38923(15) 0.92348(19) 0.13132(7) 0.0603(4) Uani d U . . 1.0 . .
C C9 0.28797(15) 0.87537(19) 0.09162(8) 0.0587(4) Uani d U . . 1.0 . .
H H9 0.2126 0.8802 0.0995 0.07 Uiso calc U . R 1.0 . .
C C13 0.3989(2) 0.9942(2) 0.19036(8) 0.0745(5) Uani d U . . 1.0 . .
C C14 0.2922(3) 1.0854(3) 0.26057(11) 0.1133(9) Uani d U . . 1.0 . .
H H14A 0.3241 1.1854 0.2591 0.136 Uiso calc U . R 1.0 . .
H H14B 0.34 1.034 0.2969 0.136 Uiso calc U . R 1.0 . .
C C15 0.1679(3) 1.0931(4) 0.26459(13) 0.1322(11) Uani d U . . 1.0 . .
H H15A 0.122 1.1463 0.229 0.198 Uiso calc U . R 1.0 . .
H H15B 0.1634 1.1445 0.3023 0.198 Uiso calc U . R 1.0 . .
H H15C 0.1369 0.9936 0.2651 0.198 Uiso calc U . R 1.0 . .
B B1 0.21742(15) 0.7545(2) -0.01482(9) 0.0544(5) Uani d U . D 1.0 . .
C C16 0.1781(7) 0.5925(9) 0.0102(5) 0.060(2) Uani d U P D 0.436(5) B 1
H H16A 0.1459 0.6135 0.0462 0.073 Uiso calc U P R 0.436(5) B 1
H H16B 0.113 0.5538 -0.0224 0.073 Uiso calc U P R 0.436(5) B 1
C C17 0.2654(6) 0.4692(7) 0.0285(4) 0.0809(19) Uani d U P D 0.436(5) B 1
H H17A 0.3293 0.5048 0.0625 0.097 Uiso calc U P R 0.436(5) B 1
H H17B 0.2995 0.4481 -0.0067 0.097 Uiso calc U P R 0.436(5) B 1
C C18 0.2194(5) 0.3221(6) 0.0492(2) 0.0820(16) Uani d U P D 0.436(5) B 1
H H18A 0.1467 0.2926 0.0195 0.098 Uiso calc U P R 0.436(5) B 1
H H18B 0.278 0.2437 0.0509 0.098 Uiso calc U P R 0.436(5) B 1
C C19 0.1972(6) 0.3426(9) 0.1091(3) 0.0931(18) Uani d U P D 0.436(5) B 1
H H19A 0.1382 0.4191 0.1069 0.14 Uiso calc U P R 0.436(5) B 1
H H19B 0.2695 0.372 0.1382 0.14 Uiso calc U P R 0.436(5) B 1
H H19C 0.1689 0.2505 0.1227 0.14 Uiso calc U P R 0.436(5) B 1
C C16A 0.1486(6) 0.6276(7) 0.0087(4) 0.0530(13) Uani d U P D 0.564(5) B 2
H H16C 0.1059 0.6694 0.0376 0.064 Uiso calc U P R 0.564(5) B 2
H H16D 0.0901 0.587 -0.0267 0.064 Uiso calc U P R 0.564(5) B 2
C C17A 0.2258(4) 0.5039(5) 0.0403(2) 0.0551(10) Uani d U P D 0.564(5) B 2
H H17C 0.2652 0.458 0.0108 0.066 Uiso calc U P R 0.564(5) B 2
H H17D 0.2868 0.5447 0.0745 0.066 Uiso calc U P R 0.564(5) B 2
C C18A 0.1581(3) 0.3877(4) 0.06523(19) 0.0598(10) Uani d U P D 0.564(5) B 2
H H18C 0.0951 0.351 0.0311 0.072 Uiso calc U P R 0.564(5) B 2
H H18D 0.1209 0.4341 0.0956 0.072 Uiso calc U P R 0.564(5) B 2
C C19A 0.2302(4) 0.2573(5) 0.0956(3) 0.0880(15) Uani d U P D 0.564(5) B 2
H H19D 0.2668 0.2094 0.066 0.132 Uiso calc U P R 0.564(5) B 2
H H19E 0.1794 0.1872 0.1097 0.132 Uiso calc U P R 0.564(5) B 2
H H19F 0.2908 0.2914 0.1308 0.132 Uiso calc U P R 0.564(5) B 2
C C20 0.1148(10) 0.8631(12) -0.0431(8) 0.055(2) Uani d U P D 0.436(5) B 1
H H20A 0.054 0.8094 -0.0733 0.066 Uiso calc U P R 0.436(5) B 1
H H20B 0.0795 0.8988 -0.0101 0.066 Uiso calc U P R 0.436(5) B 1
C C21 0.1547(6) 0.9926(8) -0.0744(4) 0.0534(17) Uani d U P D 0.436(5) B 1
H H21A 0.1833 0.9578 -0.1099 0.064 Uiso calc U P R 0.436(5) B 1
H H21B 0.2204 1.0412 -0.0454 0.064 Uiso calc U P R 0.436(5) B 1
C C22 0.0577(5) 1.1032(5) -0.0964(2) 0.0642(14) Uani d U P D 0.436(5) B 1
H H22A 0.0259 1.1333 -0.0613 0.077 Uiso calc U P R 0.436(5) B 1
H H22B -0.0061 1.0559 -0.1272 0.077 Uiso calc U P R 0.436(5) B 1
C C23 0.0988(6) 1.2400(6) -0.1250(3) 0.0964(19) Uani d U P D 0.436(5) B 1
H H23A 0.1339 1.2105 -0.1585 0.145 Uiso calc U P R 0.436(5) B 1
H H23B 0.1567 1.2925 -0.0937 0.145 Uiso calc U P R 0.436(5) B 1
H H23C 0.032 1.3044 -0.1411 0.145 Uiso calc U P R 0.436(5) B 1
C C20A 0.1353(7) 0.8962(9) -0.0452(5) 0.0540(18) Uani d U P D 0.564(5) B 2
H H20C 0.0706 0.8583 -0.0782 0.065 Uiso calc U P R 0.564(5) B 2
H H20D 0.1002 0.9378 -0.0131 0.065 Uiso calc U P R 0.564(5) B 2
C C21A 0.1932(5) 1.0212(7) -0.0719(4) 0.079(2) Uani d U P D 0.564(5) B 2
H H21C 0.2642 1.0511 -0.0409 0.095 Uiso calc U P R 0.564(5) B 2
H H21D 0.2184 0.9835 -0.108 0.095 Uiso calc U P R 0.564(5) B 2
C C22A 0.1185(5) 1.1564(7) -0.0914(3) 0.118(2) Uani d U P D 0.564(5) B 2
H H22C 0.0876 1.1898 -0.0564 0.142 Uiso calc U P R 0.564(5) B 2
H H22D 0.1685 1.2357 -0.101 0.142 Uiso calc U P R 0.564(5) B 2
C C23A 0.0222(5) 1.1342(8) -0.1437(3) 0.148(3) Uani d U P D 0.564(5) B 2
H H23D 0.0513 1.0957 -0.178 0.222 Uiso calc U P R 0.564(5) B 2
H H23E -0.0175 1.2279 -0.1557 0.222 Uiso calc U P R 0.564(5) B 2
H H23F -0.0327 1.0641 -0.1332 0.222 Uiso calc U P R 0.564(5) B 2


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.212(2) ?
O2 C13 . 1.354(3) ?
O2 C14 . 1.454(3) ?
N1 C1 . 1.298(9) ?
N1 C1A . 1.30(2) ?
N1 C4 . 1.431(2) ?
N1 B1 . 1.632(2) ?
N2 C9 . 1.343(2) ?
N2 C6 . 1.3761(19) ?
N2 B1 . 1.571(2) ?
C1 C10 . 1.486(7) ?
C1 C2 . 1.512(7) ?
C2 C12 . 1.524(7) ?
C2 C3 . 1.525(7) ?
C2 C11 . 1.532(7) ?
C3 C4 . 1.499(7) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C1A C10A . 1.489(13) ?
C1A C2A . 1.513(13) ?
C2A C11A . 1.528(14) ?
C2A C3A . 1.532(14) ?
C2A C12A . 1.537(14) ?
C3A C4 . 1.535(16) ?
C3A H3AA . 0.99 ?
C3A H3AB . 0.99 ?
C10A H10D . 0.98 ?
C10A H10E . 0.98 ?
C10A H10F . 0.98 ?
C11A H11D . 0.98 ?
C11A H11E . 0.98 ?
C11A H11F . 0.98 ?
C12A H12D . 0.98 ?
C12A H12E . 0.98 ?
C12A H12F . 0.98 ?
C4 C5 . 1.325(3) ?
C5 C6 . 1.423(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.376(2) ?
C7 C8 . 1.402(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.380(2) ?
C8 C13 . 1.454(3) ?
C9 H9 . 0.95 ?
C14 C15 . 1.495(4) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
B1 C20 . 1.576(10) ?
B1 C16A . 1.577(7) ?
B1 C20A . 1.660(7) ?
B1 C16 . 1.686(8) ?
C16 C17 . 1.514(8) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.559(8) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C19 . 1.442(8) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C16A C17A . 1.517(6) ?
C16A H16C . 0.99 ?
C16A H16D . 0.99 ?
C17A C18A . 1.514(5) ?
C17A H17C . 0.99 ?
C17A H17D . 0.99 ?
C18A C19A . 1.526(6) ?
C18A H18C . 0.99 ?
C18A H18D . 0.99 ?
C19A H19D . 0.98 ?
C19A H19E . 0.98 ?
C19A H19F . 0.98 ?
C20 C21 . 1.507(9) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 C22 . 1.517(8) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 C23 . 1.535(7) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
C20A C21A . 1.525(7) ?
C20A H20C . 0.99 ?
C20A H20D . 0.99 ?
C21A C22A . 1.518(7) ?
C21A H21C . 0.99 ?
C21A H21D . 0.99 ?
C22A C23A . 1.440(8) ?
C22A H22C . 0.99 ?
C22A H22D . 0.99 ?
C23A H23D . 0.98 ?
C23A H23E . 0.98 ?
C23A H23F . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O2 C14 . . 116.82(18) ?
C1 N1 C4 . . 108.4(4) ?
C1A N1 C4 . . 113.9(7) ?
C1 N1 B1 . . 128.4(4) ?
C1A N1 B1 . . 122.9(7) ?
C4 N1 B1 . . 123.06(13) ?
C9 N2 C6 . . 107.54(13) ?
C9 N2 B1 . . 124.51(13) ?
C6 N2 B1 . . 127.95(14) ?
N1 C1 C10 . . 124.4(7) ?
N1 C1 C2 . . 114.1(6) ?
C10 C1 C2 . . 121.5(7) ?
C1 C2 C12 . . 110.6(6) ?
C1 C2 C3 . . 100.5(5) ?
C12 C2 C3 . . 112.8(6) ?
C1 C2 C11 . . 109.8(7) ?
C12 C2 C11 . . 110.4(5) ?
C3 C2 C11 . . 112.4(5) ?
C4 C3 C2 . . 103.6(5) ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C1A C10A . . 126.4(14) ?
N1 C1A C2A . . 109.9(13) ?
C10A C1A C2A . . 123.3(16) ?
C1A C2A C11A . . 109.9(14) ?
C1A C2A C3A . . 101.6(12) ?
C11A C2A C3A . . 108.4(12) ?
C1A C2A C12A . . 113.5(15) ?
C11A C2A C12A . . 109.6(11) ?
C3A C2A C12A . . 113.5(13) ?
C2A C3A C4 . . 104.1(11) ?
C2A C3A H3AA . . 110.9 ?
C4 C3A H3AA . . 110.9 ?
C2A C3A H3AB . . 110.9 ?
C4 C3A H3AB . . 110.9 ?
H3AA C3A H3AB . . 109.0 ?
C1A C10A H10D . . 109.5 ?
C1A C10A H10E . . 109.5 ?
H10D C10A H10E . . 109.5 ?
C1A C10A H10F . . 109.5 ?
H10D C10A H10F . . 109.5 ?
H10E C10A H10F . . 109.5 ?
C2A C11A H11D . . 109.5 ?
C2A C11A H11E . . 109.5 ?
H11D C11A H11E . . 109.5 ?
C2A C11A H11F . . 109.5 ?
H11D C11A H11F . . 109.5 ?
H11E C11A H11F . . 109.5 ?
C2A C12A H12D . . 109.5 ?
C2A C12A H12E . . 109.5 ?
H12D C12A H12E . . 109.5 ?
C2A C12A H12F . . 109.5 ?
H12D C12A H12F . . 109.5 ?
H12E C12A H12F . . 109.5 ?
C5 C4 N1 . . 121.55(16) ?
C5 C4 C3 . . 129.0(3) ?
N1 C4 C3 . . 108.9(3) ?
C5 C4 C3A . . 132.9(5) ?
N1 C4 C3A . . 104.3(5) ?
C4 C5 C6 . . 124.13(15) ?
C4 C5 H5 . . 117.9 ?
C6 C5 H5 . . 117.9 ?
C7 C6 N2 . . 108.84(15) ?
C7 C6 C5 . . 132.52(15) ?
N2 C6 C5 . . 118.63(15) ?
C6 C7 C8 . . 107.17(14) ?
C6 C7 H7 . . 126.4 ?
C8 C7 H7 . . 126.4 ?
C9 C8 C7 . . 106.19(15) ?
C9 C8 C13 . . 126.52(18) ?
C7 C8 C13 . . 127.23(17) ?
N2 C9 C8 . . 110.26(15) ?
N2 C9 H9 . . 124.9 ?
C8 C9 H9 . . 124.9 ?
O1 C13 O2 . . 122.5(2) ?
O1 C13 C8 . . 125.4(2) ?
O2 C13 C8 . . 112.15(16) ?
O2 C14 C15 . . 107.3(2) ?
O2 C14 H14A . . 110.3 ?
C15 C14 H14A . . 110.3 ?
O2 C14 H14B . . 110.3 ?
C15 C14 H14B . . 110.3 ?
H14A C14 H14B . . 108.5 ?
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 ?
N2 B1 C20 . . 113.9(6) ?
N2 B1 C16A . . 110.0(3) ?
N2 B1 N1 . . 104.64(12) ?
C20 B1 N1 . . 112.3(6) ?
C16A B1 N1 . . 115.5(3) ?
N2 B1 C20A . . 104.9(4) ?
C16A B1 C20A . . 114.2(4) ?
N1 B1 C20A . . 106.6(4) ?
N2 B1 C16 . . 105.9(4) ?
C20 B1 C16 . . 116.0(5) ?
N1 B1 C16 . . 102.9(4) ?
C17 C16 B1 . . 121.1(5) ?
C17 C16 H16A . . 107.0 ?
B1 C16 H16A . . 107.0 ?
C17 C16 H16B . . 107.0 ?
B1 C16 H16B . . 107.0 ?
H16A C16 H16B . . 106.8 ?
C16 C17 C18 . . 117.1(5) ?
C16 C17 H17A . . 108.0 ?
C18 C17 H17A . . 108.0 ?
C16 C17 H17B . . 108.0 ?
C18 C17 H17B . . 108.0 ?
H17A C17 H17B . . 107.3 ?
C19 C18 C17 . . 108.7(6) ?
C19 C18 H18A . . 109.9 ?
C17 C18 H18A . . 109.9 ?
C19 C18 H18B . . 109.9 ?
C17 C18 H18B . . 109.9 ?
H18A C18 H18B . . 108.3 ?
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 ?
C17A C16A B1 . . 113.7(4) ?
C17A C16A H16C . . 108.8 ?
B1 C16A H16C . . 108.8 ?
C17A C16A H16D . . 108.8 ?
B1 C16A H16D . . 108.8 ?
H16C C16A H16D . . 107.7 ?
C18A C17A C16A . . 112.4(4) ?
C18A C17A H17C . . 109.1 ?
C16A C17A H17C . . 109.1 ?
C18A C17A H17D . . 109.1 ?
C16A C17A H17D . . 109.1 ?
H17C C17A H17D . . 107.9 ?
C17A C18A C19A . . 115.0(3) ?
C17A C18A H18C . . 108.5 ?
C19A C18A H18C . . 108.5 ?
C17A C18A H18D . . 108.5 ?
C19A C18A H18D . . 108.5 ?
H18C C18A H18D . . 107.5 ?
C18A C19A H19D . . 109.5 ?
C18A C19A H19E . . 109.5 ?
H19D C19A H19E . . 109.5 ?
C18A C19A H19F . . 109.5 ?
H19D C19A H19F . . 109.5 ?
H19E C19A H19F . . 109.5 ?
C21 C20 B1 . . 112.6(8) ?
C21 C20 H20A . . 109.1 ?
B1 C20 H20A . . 109.1 ?
C21 C20 H20B . . 109.1 ?
B1 C20 H20B . . 109.1 ?
H20A C20 H20B . . 107.8 ?
C20 C21 C22 . . 112.1(6) ?
C20 C21 H21A . . 109.2 ?
C22 C21 H21A . . 109.2 ?
C20 C21 H21B . . 109.2 ?
C22 C21 H21B . . 109.2 ?
H21A C21 H21B . . 107.9 ?
C21 C22 C23 . . 112.7(5) ?
C21 C22 H22A . . 109.0 ?
C23 C22 H22A . . 109.0 ?
C21 C22 H22B . . 109.0 ?
C23 C22 H22B . . 109.0 ?
H22A C22 H22B . . 107.8 ?
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 ?
C21A C20A B1 . . 118.0(6) ?
C21A C20A H20C . . 107.8 ?
B1 C20A H20C . . 107.8 ?
C21A C20A H20D . . 107.8 ?
B1 C20A H20D . . 107.8 ?
H20C C20A H20D . . 107.1 ?
C22A C21A C20A . . 115.8(5) ?
C22A C21A H21C . . 108.3 ?
C20A C21A H21C . . 108.3 ?
C22A C21A H21D . . 108.3 ?
C20A C21A H21D . . 108.3 ?
H21C C21A H21D . . 107.4 ?
C23A C22A C21A . . 114.3(6) ?
C23A C22A H22C . . 108.7 ?
C21A C22A H22C . . 108.7 ?
C23A C22A H22D . . 108.7 ?
C21A C22A H22D . . 108.7 ?
H22C C22A H22D . . 107.6 ?
C22A C23A H23D . . 109.5 ?
C22A C23A H23E . . 109.5 ?
H23D C23A H23E . . 109.5 ?
C22A C23A H23F . . 109.5 ?
H23D C23A H23F . . 109.5 ?
H23E C23A H23F . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C10 . . . . -173.3(10) ?
B1 N1 C1 C10 . . . . 2.3(16) ?
C4 N1 C1 C2 . . . . 9.1(11) ?
B1 N1 C1 C2 . . . . -175.3(5) ?
N1 C1 C2 C12 . . . . -138.4(9) ?
C10 C1 C2 C12 . . . . 43.9(13) ?
N1 C1 C2 C3 . . . . -19.0(11) ?
C10 C1 C2 C3 . . . . 163.3(10) ?
N1 C1 C2 C11 . . . . 99.6(10) ?
C10 C1 C2 C11 . . . . -78.1(12) ?
C1 C2 C3 C4 . . . . 19.8(8) ?
C12 C2 C3 C4 . . . . 137.7(6) ?
C11 C2 C3 C4 . . . . -96.8(6) ?
C4 N1 C1A C10A . . . . 175.(2) ?
B1 N1 C1A C10A . . . . 0.(3) ?
C4 N1 C1A C2A . . . . -12.(2) ?
B1 N1 C1A C2A . . . . 172.6(10) ?
N1 C1A C2A C11A . . . . 137.0(18) ?
C10A C1A C2A C11A . . . . -50.(3) ?
N1 C1A C2A C3A . . . . 22.(2) ?
C10A C1A C2A C3A . . . . -164.(2) ?
N1 C1A C2A C12A . . . . -100.(2) ?
C10A C1A C2A C12A . . . . 73.(3) ?
C1A C2A C3A C4 . . . . -23.7(19) ?
C11A C2A C3A C4 . . . . -139.4(14) ?
C12A C2A C3A C4 . . . . 98.5(15) ?
C1 N1 C4 C5 . . . . 177.9(7) ?
C1A N1 C4 C5 . . . . -173.8(14) ?
B1 N1 C4 C5 . . . . 2.0(3) ?
C1 N1 C4 C3 . . . . 5.3(7) ?
B1 N1 C4 C3 . . . . -170.5(3) ?
C1A N1 C4 C3A . . . . -4.7(16) ?
B1 N1 C4 C3A . . . . 171.1(8) ?
C2 C3 C4 C5 . . . . 171.5(4) ?
C2 C3 C4 N1 . . . . -16.7(5) ?
C2A C3A C4 C5 . . . . -174.4(7) ?
C2A C3A C4 N1 . . . . 18.3(13) ?
N1 C4 C5 C6 . . . . -0.9(3) ?
C3 C4 C5 C6 . . . . 170.0(4) ?
C3A C4 C5 C6 . . . . -166.4(10) ?
C9 N2 C6 C7 . . . . 0.25(18) ?
B1 N2 C6 C7 . . . . -179.35(15) ?
C9 N2 C6 C5 . . . . -178.59(16) ?
B1 N2 C6 C5 . . . . 1.8(2) ?
C4 C5 C6 C7 . . . . -179.50(19) ?
C4 C5 C6 N2 . . . . -1.0(3) ?
N2 C6 C7 C8 . . . . -0.17(19) ?
C5 C6 C7 C8 . . . . 178.46(18) ?
C6 C7 C8 C9 . . . . 0.02(19) ?
C6 C7 C8 C13 . . . . -177.35(17) ?
C6 N2 C9 C8 . . . . -0.24(19) ?
B1 N2 C9 C8 . . . . 179.38(14) ?
C7 C8 C9 N2 . . . . 0.1(2) ?
C13 C8 C9 N2 . . . . 177.53(16) ?
C14 O2 C13 O1 . . . . 4.2(3) ?
C14 O2 C13 C8 . . . . -175.06(19) ?
C9 C8 C13 O1 . . . . -177.20(19) ?
C7 C8 C13 O1 . . . . -0.3(3) ?
C9 C8 C13 O2 . . . . 2.0(3) ?
C7 C8 C13 O2 . . . . 178.87(17) ?
C13 O2 C14 C15 . . . . 175.9(2) ?
C9 N2 B1 C20 . . . . 56.7(6) ?
C6 N2 B1 C20 . . . . -123.8(6) ?
C9 N2 B1 C16A . . . . -55.6(3) ?
C6 N2 B1 C16A . . . . 124.0(3) ?
C9 N2 B1 N1 . . . . 179.74(14) ?
C6 N2 B1 N1 . . . . -0.7(2) ?
C9 N2 B1 C20A . . . . 67.7(4) ?
C6 N2 B1 C20A . . . . -112.8(4) ?
C9 N2 B1 C16 . . . . -71.9(4) ?
C6 N2 B1 C16 . . . . 107.6(3) ?
C1 N1 B1 N2 . . . . -176.2(8) ?
C1A N1 B1 N2 . . . . 174.3(16) ?
C4 N1 B1 N2 . . . . -1.2(2) ?
C1 N1 B1 C20 . . . . -52.1(9) ?
C4 N1 B1 C20 . . . . 122.9(5) ?
C1A N1 B1 C16A . . . . 53.2(16) ?
C4 N1 B1 C16A . . . . -122.3(3) ?
C1A N1 B1 C20A . . . . -74.9(16) ?
C4 N1 B1 C20A . . . . 109.6(4) ?
C1 N1 B1 C16 . . . . 73.4(9) ?
C4 N1 B1 C16 . . . . -111.6(4) ?
N2 B1 C16 C17 . . . . -62.9(9) ?
C20 B1 C16 C17 . . . . 169.7(10) ?
N1 B1 C16 C17 . . . . 46.7(9) ?
B1 C16 C17 C18 . . . . -178.2(7) ?
C16 C17 C18 C19 . . . . -72.5(9) ?
N2 B1 C16A C17A . . . . -58.3(5) ?
N1 B1 C16A C17A . . . . 59.9(6) ?
C20A B1 C16A C17A . . . . -175.9(6) ?
B1 C16A C17A C18A . . . . 177.0(4) ?
C16A C17A C18A C19A . . . . 177.9(5) ?
N2 B1 C20 C21 . . . . 66.9(12) ?
N1 B1 C20 C21 . . . . -51.8(11) ?
C16 B1 C20 C21 . . . . -169.8(8) ?
B1 C20 C21 C22 . . . . -174.9(8) ?
C20 C21 C22 C23 . . . . 176.7(8) ?
N2 B1 C20A C21A . . . . 62.3(9) ?
C16A B1 C20A C21A . . . . -177.2(7) ?
N1 B1 C20A C21A . . . . -48.3(9) ?
B1 C20A C21A C22A . . . . -172.3(7) ?
C20A C21A C22A C23A . . . . -68.1(10) ?

####################################################################### 
# 
# 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_rds643
_database_code_depnum_ccdc_archive 'CCDC 1900107'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;NCSU
United States of America
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            BF2-BrDHDP
_chemical_formula_moiety         'C15 H18 B Br F2 N2 O2'
_chemical_formula_sum            'C15 H18 B Br F2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         387.03

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1235(2)
_cell_length_b                   11.0063(3)
_cell_length_c                   11.5158(3)
_cell_angle_alpha                66.4695(11)
_cell_angle_beta                 84.0270(12)
_cell_angle_gamma                83.5531(13)
_cell_volume                     820.83(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    246
_cell_measurement_theta_min      2.1401
_cell_measurement_theta_max      33.2195
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.212
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392

_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.62

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            52690
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         36.54
_diffrn_reflns_theta_full        36.54
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             8056
_reflns_number_gt                7102
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0608
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_number_reflns         8056
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+0.1607P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.81359(2) 0.71453(2) 0.14380(2) 0.01715(3) Uani d . . . 1 . .
F F1 0.21066(8) 0.32753(6) 0.48290(6) 0.01818(10) Uani d . . . 1 . .
F F2 0.38485(9) 0.19823(6) 0.39311(5) 0.01909(11) Uani d . . . 1 . .
O O2 0.26260(10) 0.64890(7) -0.03124(6) 0.01665(12) Uani d . . . 1 . .
N N2 0.45351(10) 0.42651(7) 0.31923(7) 0.01179(11) Uani d . . . 1 . .
N N1 0.53879(10) 0.26289(7) 0.53494(7) 0.01135(11) Uani d . . . 1 . .
O O1 0.51194(11) 0.77267(7) -0.07368(7) 0.02248(14) Uani d . . . 1 . .
C C5 0.72823(12) 0.44792(8) 0.41896(8) 0.01223(13) Uani d . . . 1 . .
H H5 0.8335 0.4961 0.414 0.015 Uiso calc U . R 1 . .
C C7 0.62204(12) 0.59672(8) 0.19634(8) 0.01246(13) Uani d . . . 1 . .
C C4 0.69440(11) 0.33916(8) 0.52372(8) 0.01145(12) Uani d . . . 1 . .
C C1 0.54673(12) 0.15313(8) 0.63622(8) 0.01248(13) Uani d . . . 1 . .
C C6 0.60939(11) 0.49341(8) 0.31407(8) 0.01157(12) Uani d . . . 1 . .
C C3 0.79437(12) 0.27529(8) 0.64399(8) 0.01341(13) Uani d . . . 1 . .
H H3A 0.7578 0.3229 0.7009 0.016 Uiso calc U . R 1 . .
H H3B 0.9335 0.2731 0.6264 0.016 Uiso calc U . R 1 . .
B B13 0.38715(13) 0.30298(9) 0.43076(9) 0.01239(14) Uani d . . . 1 . .
C C8 0.47106(12) 0.59275(8) 0.12643(8) 0.01269(13) Uani d . . . 1 . .
C C13 0.42278(12) 0.68128(8) -0.00194(8) 0.01380(14) Uani d . . . 1 . .
C C9 0.37119(12) 0.48619(8) 0.20669(8) 0.01326(13) Uani d . . . 1 . .
H H9 0.2616 0.459 0.1861 0.016 Uiso calc U . R 1 . .
C C2 0.72673(12) 0.13368(8) 0.70267(8) 0.01448(14) Uani d . . . 1 . .
C C10 0.40360(13) 0.05430(9) 0.67836(9) 0.01744(15) Uani d . . . 1 . .
H H10A 0.3382 0.0521 0.7583 0.026 Uiso calc U . R 1 . .
H H10B 0.4661 -0.0337 0.6912 0.026 Uiso calc U . R 1 . .
H H10C 0.3116 0.079 0.6135 0.026 Uiso calc U . R 1 . .
C C14 0.20078(13) 0.72982(9) -0.15653(8) 0.01720(15) Uani d . . . 1 . .
H H14A 0.3022 0.7288 -0.2219 0.021 Uiso calc U . R 1 . .
H H14B 0.1694 0.8229 -0.1653 0.021 Uiso calc U . R 1 . .
C C11 0.69866(16) 0.07701(10) 0.84723(9) 0.02264(19) Uani d . . . 1 . .
H H11A 0.6003 0.1324 0.8733 0.034 Uiso calc U . R 1 . .
H H11B 0.8177 0.0761 0.8834 0.034 Uiso calc U . R 1 . .
H H11C 0.66 -0.0139 0.8778 0.034 Uiso calc U . R 1 . .
C C15 0.02796(14) 0.67207(10) -0.17280(9) 0.01853(16) Uani d . . . 1 . .
H H15A -0.0102 0.719 -0.26 0.028 Uiso calc U . R 1 . .
H H15B -0.0756 0.6821 -0.1135 0.028 Uiso calc U . R 1 . .
H H15C 0.0574 0.5775 -0.1555 0.028 Uiso calc U . R 1 . .
C C12 0.86100(15) 0.03837(11) 0.65799(12) 0.0253(2) Uani d . . . 1 . .
H H12A 0.8014 -0.0447 0.68 0.038 Uiso calc U . R 1 . .
H H12B 0.9801 0.0194 0.6998 0.038 Uiso calc U . R 1 . .
H H12C 0.8867 0.0799 0.5658 0.038 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C7 . 1.8730(8) ?
F1 B13 . 1.3822(11) ?
F2 B13 . 1.3864(11) ?
O2 C13 . 1.3455(11) ?
O2 C14 . 1.4447(11) ?
N2 C9 . 1.3589(11) ?
N2 C6 . 1.3834(10) ?
N2 B13 . 1.5314(11) ?
N1 C1 . 1.3025(10) ?
N1 C4 . 1.4292(10) ?
N1 B13 . 1.5940(11) ?
O1 C13 . 1.2117(10) ?
C5 C4 . 1.3407(11) ?
C5 C6 . 1.4357(11) ?
C5 H5 . 0.95 ?
C7 C6 . 1.3805(11) ?
C7 C8 . 1.4232(11) ?
C4 C3 . 1.4951(11) ?
C1 C10 . 1.4774(12) ?
C1 C2 . 1.5124(12) ?
C3 C2 . 1.5421(12) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C8 C9 . 1.3860(11) ?
C8 C13 . 1.4607(12) ?
C9 H9 . 0.95 ?
C2 C11 . 1.5264(13) ?
C2 C12 . 1.5437(14) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C14 C15 . 1.5077(13) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O2 C14 . . 115.85(7) ?
C9 N2 C6 . . 108.61(7) ?
C9 N2 B13 . . 125.21(7) ?
C6 N2 B13 . . 126.15(7) ?
C1 N1 C4 . . 110.77(7) ?
C1 N1 B13 . . 125.25(7) ?
C4 N1 B13 . . 123.81(6) ?
C4 C5 C6 . . 121.65(7) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C6 C7 C8 . . 108.07(7) ?
C6 C7 Br1 . . 123.58(6) ?
C8 C7 Br1 . . 128.33(6) ?
C5 C4 N1 . . 121.15(7) ?
C5 C4 C3 . . 131.12(7) ?
N1 C4 C3 . . 107.73(7) ?
N1 C1 C10 . . 124.59(8) ?
N1 C1 C2 . . 112.06(7) ?
C10 C1 C2 . . 123.26(7) ?
C7 C6 N2 . . 107.82(7) ?
C7 C6 C5 . . 131.62(7) ?
N2 C6 C5 . . 120.51(7) ?
C4 C3 C2 . . 103.31(7) ?
C4 C3 H3A . . 111.1 ?
C2 C3 H3A . . 111.1 ?
C4 C3 H3B . . 111.1 ?
C2 C3 H3B . . 111.1 ?
H3A C3 H3B . . 109.1 ?
F1 B13 F2 . . 110.04(7) ?
F1 B13 N2 . . 111.94(7) ?
F2 B13 N2 . . 110.56(7) ?
F1 B13 N1 . . 109.28(7) ?
F2 B13 N1 . . 108.32(7) ?
N2 B13 N1 . . 106.58(6) ?
C9 C8 C7 . . 105.72(7) ?
C9 C8 C13 . . 125.27(8) ?
C7 C8 C13 . . 129.00(7) ?
O1 C13 O2 . . 123.54(8) ?
O1 C13 C8 . . 125.60(8) ?
O2 C13 C8 . . 110.85(7) ?
N2 C9 C8 . . 109.78(7) ?
N2 C9 H9 . . 125.1 ?
C8 C9 H9 . . 125.1 ?
C1 C2 C11 . . 114.01(8) ?
C1 C2 C3 . . 101.43(7) ?
C11 C2 C3 . . 114.08(7) ?
C1 C2 C12 . . 105.26(7) ?
C11 C2 C12 . . 110.61(8) ?
C3 C2 C12 . . 110.82(8) ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O2 C14 C15 . . 107.30(7) ?
O2 C14 H14A . . 110.3 ?
C15 C14 H14A . . 110.3 ?
O2 C14 H14B . . 110.3 ?
C15 C14 H14B . . 110.3 ?
H14A C14 H14B . . 108.5 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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 ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C5 C4 N1 . . . . 0.56(13) ?
C6 C5 C4 C3 . . . . -178.63(8) ?
C1 N1 C4 C5 . . . . 171.77(8) ?
B13 N1 C4 C5 . . . . -3.69(12) ?
C1 N1 C4 C3 . . . . -8.87(9) ?
B13 N1 C4 C3 . . . . 175.67(7) ?
C4 N1 C1 C10 . . . . 177.60(8) ?
B13 N1 C1 C10 . . . . -7.03(14) ?
C4 N1 C1 C2 . . . . -5.83(10) ?
B13 N1 C1 C2 . . . . 169.54(7) ?
C8 C7 C6 N2 . . . . -0.59(10) ?
Br1 C7 C6 N2 . . . . -179.10(6) ?
C8 C7 C6 C5 . . . . 176.91(9) ?
Br1 C7 C6 C5 . . . . -1.61(14) ?
C9 N2 C6 C7 . . . . 0.43(10) ?
B13 N2 C6 C7 . . . . 178.54(8) ?
C9 N2 C6 C5 . . . . -177.40(8) ?
B13 N2 C6 C5 . . . . 0.71(13) ?
C4 C5 C6 C7 . . . . -176.27(9) ?
C4 C5 C6 N2 . . . . 0.96(13) ?
C5 C4 C3 C2 . . . . -161.80(9) ?
N1 C4 C3 C2 . . . . 18.93(9) ?
C9 N2 B13 F1 . . . . -65.90(11) ?
C6 N2 B13 F1 . . . . 116.29(9) ?
C9 N2 B13 F2 . . . . 57.15(11) ?
C6 N2 B13 F2 . . . . -120.65(9) ?
C9 N2 B13 N1 . . . . 174.67(8) ?
C6 N2 B13 N1 . . . . -3.14(11) ?
C1 N1 B13 F1 . . . . 68.65(10) ?
C4 N1 B13 F1 . . . . -116.56(8) ?
C1 N1 B13 F2 . . . . -51.24(11) ?
C4 N1 B13 F2 . . . . 123.56(8) ?
C1 N1 B13 N2 . . . . -170.22(8) ?
C4 N1 B13 N2 . . . . 4.58(11) ?
C6 C7 C8 C9 . . . . 0.52(10) ?
Br1 C7 C8 C9 . . . . 178.95(7) ?
C6 C7 C8 C13 . . . . 179.40(9) ?
Br1 C7 C8 C13 . . . . -2.18(14) ?
C14 O2 C13 O1 . . . . 0.59(13) ?
C14 O2 C13 C8 . . . . -179.89(7) ?
C9 C8 C13 O1 . . . . -178.16(10) ?
C7 C8 C13 O1 . . . . 3.17(16) ?
C9 C8 C13 O2 . . . . 2.32(13) ?
C7 C8 C13 O2 . . . . -176.35(9) ?
C6 N2 C9 C8 . . . . -0.10(10) ?
B13 N2 C9 C8 . . . . -178.23(8) ?
C7 C8 C9 N2 . . . . -0.26(10) ?
C13 C8 C9 N2 . . . . -179.19(8) ?
N1 C1 C2 C11 . . . . 140.32(8) ?
C10 C1 C2 C11 . . . . -43.05(12) ?
N1 C1 C2 C3 . . . . 17.25(9) ?
C10 C1 C2 C3 . . . . -166.13(8) ?
N1 C1 C2 C12 . . . . -98.28(9) ?
C10 C1 C2 C12 . . . . 78.34(10) ?
C4 C3 C2 C1 . . . . -20.76(8) ?
C4 C3 C2 C11 . . . . -143.78(8) ?
C4 C3 C2 C12 . . . . 90.59(9) ?
C13 O2 C14 C15 . . . . 176.51(8) ?

####################################################################### 
# 
# 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_rds644
_database_code_depnum_ccdc_archive 'CCDC 1900106'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;NCSU
United States of America
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-04-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            BBu2-BrDHDP
_chemical_formula_moiety         'C23 H36 B Br N2 O2'
_chemical_formula_sum            'C23 H36 B Br N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         463.26
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      hexagonal
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'

_cell_length_a                   9.6838(2)
_cell_length_b                   9.6838(2)
_cell_length_c                   43.5738(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3538.73(16)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    378
_cell_measurement_theta_min      8.9764
_cell_measurement_theta_max      31.5966
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.184
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464

_exptl_absorpt_coefficient_mu    1.763
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'mu from formula'
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.74

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            185013
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_full        33.16
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_limit_l_max       67

_refine_special_details          
;
;

_reflns_number_total             8999
_reflns_number_gt                8737
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0779
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_number_reflns         8999
_refine_ls_number_parameters     268
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+1.7615P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.533
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 4023 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0114(15)

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'
Br Br -0.2901 2.4595 '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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 786)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.14204(3) -0.06890(3) 0.14699(2) 0.02082(6) Uani d . . . 1 . .
O O1 -0.0570(3) 0.1325(3) 0.21166(5) 0.0263(4) Uani d . . . 1 . .
O O2 0.1713(3) 0.3703(2) 0.21642(4) 0.0234(4) Uani d . . . 1 . .
N N1 0.3775(2) 0.3453(2) 0.07308(4) 0.0128(3) Uani d . . . 1 . .
N N2 0.2679(2) 0.3357(2) 0.12636(4) 0.0136(3) Uani d . . . 1 . .
C C1 0.4612(3) 0.3923(3) 0.04771(5) 0.0153(4) Uani d . . . 1 . .
C C2 0.3916(3) 0.2704(3) 0.02222(5) 0.0168(4) Uani d . . . 1 . .
C C3 0.2666(3) 0.1205(3) 0.03943(5) 0.0174(4) Uani d . . . 1 . .
H H3A 0.1647 0.0662 0.028 0.021 Uiso calc U . R 1 . .
H H3B 0.3053 0.0445 0.0428 0.021 Uiso calc U . R 1 . .
C C4 0.2471(3) 0.1856(3) 0.06930(5) 0.0138(4) Uani d . . . 1 . .
C C5 0.1333(3) 0.1148(3) 0.09052(5) 0.0150(4) Uani d . . . 1 . .
H H5 0.0448 0.0123 0.0863 0.018 Uiso calc U . R 1 . .
C C6 0.1401(3) 0.1879(3) 0.11953(5) 0.0136(3) Uani d . . . 1 . .
C C7 0.0431(3) 0.1311(3) 0.14516(6) 0.0162(4) Uani d . . . 1 . .
C C8 0.1155(3) 0.2458(3) 0.16885(5) 0.0152(4) Uani d . . . 1 . .
C C9 0.2531(3) 0.3699(3) 0.15593(5) 0.0138(4) Uani d . . . 1 . .
H H9 0.3262 0.4649 0.1663 0.017 Uiso calc U . R 1 . .
C C10 0.6058(3) 0.5494(3) 0.04285(6) 0.0225(5) Uani d . . . 1 . .
H H10A 0.6081 0.6258 0.0579 0.034 Uiso calc U . R 1 . .
H H10B 0.6043 0.5872 0.0221 0.034 Uiso calc U . R 1 . .
H H10C 0.7008 0.5391 0.0454 0.034 Uiso calc U . R 1 . .
C C11 0.3116(3) 0.3289(4) -0.00070(6) 0.0252(5) Uani d . . . 1 . .
H H11A 0.3905 0.4344 -0.0084 0.038 Uiso calc U . R 1 . .
H H11B 0.2253 0.3359 0.0096 0.038 Uiso calc U . R 1 . .
H H11C 0.2678 0.2538 -0.0179 0.038 Uiso calc U . R 1 . .
C C12 0.5181(3) 0.2467(4) 0.00587(6) 0.0250(5) Uani d . . . 1 . .
H H12A 0.4668 0.1629 -0.0097 0.037 Uiso calc U . R 1 . .
H H12B 0.5729 0.2154 0.0209 0.037 Uiso calc U . R 1 . .
H H12C 0.5956 0.3466 -0.0041 0.037 Uiso calc U . R 1 . .
C C13 0.3557(3) 0.5905(3) 0.09310(6) 0.0179(4) Uani d . . . 1 . .
H H13A 0.3761 0.6613 0.111 0.021 Uiso calc U . R 1 . .
H H13B 0.4315 0.6559 0.0768 0.021 Uiso calc U . R 1 . .
C C14 0.1875(3) 0.5364(3) 0.08159(7) 0.0243(5) Uani d . . . 1 . .
H H14A 0.1657 0.4672 0.0634 0.029 Uiso calc U . R 1 . .
H H14B 0.11 0.4722 0.0978 0.029 Uiso calc U . R 1 . .
C C15 0.1632(3) 0.6751(3) 0.07300(7) 0.0244(5) Uani d . . . 1 . .
H H15A 0.1843 0.7436 0.0913 0.029 Uiso calc U . R 1 . .
H H15B 0.242 0.74 0.0571 0.029 Uiso calc U . R 1 . .
C C16 -0.0031(4) 0.6240(4) 0.06112(9) 0.0346(7) Uani d . . . 1 . .
H H16A -0.0229 0.5611 0.0424 0.052 Uiso calc U . R 1 . .
H H16B -0.0115 0.7187 0.0566 0.052 Uiso calc U . R 1 . .
H H16C -0.0821 0.5593 0.0767 0.052 Uiso calc U . R 1 . .
C C17 0.5719(3) 0.5289(3) 0.11895(6) 0.0174(4) Uani d . . . 1 . .
H H17A 0.6523 0.6023 0.104 0.021 Uiso calc U . R 1 . .
H H17B 0.5749 0.5938 0.1368 0.021 Uiso calc U . R 1 . .
C C18 0.6226(3) 0.4115(3) 0.12989(7) 0.0245(5) Uani d . . . 1 . .
H H18A 0.6366 0.3583 0.1117 0.029 Uiso calc U . R 1 . .
H H18B 0.5355 0.3285 0.1425 0.029 Uiso calc U . R 1 . .
C C19 0.7758(3) 0.4857(3) 0.14867(7) 0.0262(5) Uani d . . . 1 . .
H H19A 0.8656 0.5584 0.1353 0.031 Uiso calc U . R 1 . .
H H19B 0.7672 0.5506 0.1653 0.031 Uiso calc U . R 1 . .
C C20 0.8144(4) 0.3657(4) 0.16282(8) 0.0333(7) Uani d . . . 1 . .
H H20A 0.8276 0.3035 0.1465 0.05 Uiso calc U . R 1 . .
H H20B 0.7272 0.294 0.1764 0.05 Uiso calc U . R 1 . .
H H20C 0.9134 0.4222 0.1747 0.05 Uiso calc U . R 1 . .
C C21 0.0631(3) 0.2387(3) 0.20054(6) 0.0189(4) Uani d . . . 1 . .
C C22 0.1373(4) 0.3751(4) 0.24865(6) 0.0274(6) Uani d . . . 1 . .
H H22A 0.2385 0.4303 0.2603 0.033 Uiso calc U . R 1 . .
H H22B 0.0744 0.265 0.2567 0.033 Uiso calc U . R 1 . .
C C23 0.0457(4) 0.4609(4) 0.25316(7) 0.0285(6) Uani d . . . 1 . .
H H23A -0.0531 0.408 0.2412 0.043 Uiso calc U . R 1 . .
H H23B 0.1105 0.5716 0.2463 0.043 Uiso calc U . R 1 . .
H H23C 0.0198 0.4591 0.275 0.043 Uiso calc U . R 1 . .
B B1 0.3979(3) 0.4548(3) 0.10313(6) 0.0144(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C7 . 1.871(2) ?
O1 C21 . 1.204(3) ?
O2 C21 . 1.366(3) ?
O2 C22 . 1.449(3) ?
N1 C1 . 1.310(3) ?
N1 C4 . 1.435(3) ?
N1 B1 . 1.634(3) ?
N2 C9 . 1.356(3) ?
N2 C6 . 1.377(3) ?
N2 B1 . 1.577(3) ?
C1 C10 . 1.480(3) ?
C1 C2 . 1.512(3) ?
C2 C12 . 1.530(4) ?
C2 C11 . 1.536(3) ?
C2 C3 . 1.542(3) ?
C3 C4 . 1.498(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.336(3) ?
C5 C6 . 1.434(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.384(3) ?
C7 C8 . 1.419(3) ?
C8 C9 . 1.391(3) ?
C8 C21 . 1.461(3) ?
C9 H9 . 0.95 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.525(4) ?
C13 B1 . 1.619(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.522(4) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.519(4) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 C18 . 1.523(4) ?
C17 B1 . 1.619(4) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C19 . 1.524(4) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.517(4) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C22 C23 . 1.501(4) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 O2 C22 . . 116.1(2) ?
C1 N1 C4 . . 109.59(19) ?
C1 N1 B1 . . 126.72(19) ?
C4 N1 B1 . . 123.16(18) ?
C9 N2 C6 . . 108.01(19) ?
C9 N2 B1 . . 125.09(19) ?
C6 N2 B1 . . 126.51(19) ?
N1 C1 C10 . . 125.5(2) ?
N1 C1 C2 . . 113.1(2) ?
C10 C1 C2 . . 121.4(2) ?
C1 C2 C12 . . 112.4(2) ?
C1 C2 C11 . . 107.4(2) ?
C12 C2 C11 . . 110.0(2) ?
C1 C2 C3 . . 102.20(18) ?
C12 C2 C3 . . 113.3(2) ?
C11 C2 C3 . . 111.1(2) ?
C4 C3 C2 . . 103.36(19) ?
C4 C3 H3A . . 111.1 ?
C2 C3 H3A . . 111.1 ?
C4 C3 H3B . . 111.1 ?
C2 C3 H3B . . 111.1 ?
H3A C3 H3B . . 109.1 ?
C5 C4 N1 . . 121.9(2) ?
C5 C4 C3 . . 129.1(2) ?
N1 C4 C3 . . 108.98(18) ?
C4 C5 C6 . . 122.3(2) ?
C4 C5 H5 . . 118.9 ?
C6 C5 H5 . . 118.9 ?
N2 C6 C7 . . 108.5(2) ?
N2 C6 C5 . . 119.9(2) ?
C7 C6 C5 . . 131.3(2) ?
C6 C7 C8 . . 107.72(19) ?
C6 C7 Br1 . . 123.70(19) ?
C8 C7 Br1 . . 128.48(18) ?
C9 C8 C7 . . 105.47(19) ?
C9 C8 C21 . . 125.7(2) ?
C7 C8 C21 . . 128.8(2) ?
N2 C9 C8 . . 110.3(2) ?
N2 C9 H9 . . 124.9 ?
C8 C9 H9 . . 124.9 ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 B1 . . 118.0(2) ?
C14 C13 H13A . . 107.8 ?
B1 C13 H13A . . 107.8 ?
C14 C13 H13B . . 107.8 ?
B1 C13 H13B . . 107.8 ?
H13A C13 H13B . . 107.1 ?
C15 C14 C13 . . 112.8(2) ?
C15 C14 H14A . . 109.0 ?
C13 C14 H14A . . 109.0 ?
C15 C14 H14B . . 109.0 ?
C13 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
C16 C15 C14 . . 113.7(2) ?
C16 C15 H15A . . 108.8 ?
C14 C15 H15A . . 108.8 ?
C16 C15 H15B . . 108.8 ?
C14 C15 H15B . . 108.8 ?
H15A C15 H15B . . 107.7 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 B1 . . 117.0(2) ?
C18 C17 H17A . . 108.0 ?
B1 C17 H17A . . 108.0 ?
C18 C17 H17B . . 108.0 ?
B1 C17 H17B . . 108.0 ?
H17A C17 H17B . . 107.3 ?
C17 C18 C19 . . 114.7(2) ?
C17 C18 H18A . . 108.6 ?
C19 C18 H18A . . 108.6 ?
C17 C18 H18B . . 108.6 ?
C19 C18 H18B . . 108.6 ?
H18A C18 H18B . . 107.6 ?
C20 C19 C18 . . 114.3(2) ?
C20 C19 H19A . . 108.7 ?
C18 C19 H19A . . 108.7 ?
C20 C19 H19B . . 108.7 ?
C18 C19 H19B . . 108.7 ?
H19A C19 H19B . . 107.6 ?
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 ?
O1 C21 O2 . . 123.8(2) ?
O1 C21 C8 . . 125.8(2) ?
O2 C21 C8 . . 110.4(2) ?
O2 C22 C23 . . 110.6(2) ?
O2 C22 H22A . . 109.5 ?
C23 C22 H22A . . 109.5 ?
O2 C22 H22B . . 109.5 ?
C23 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
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 ?
N2 B1 C17 . . 108.94(19) ?
N2 B1 C13 . . 109.49(19) ?
C17 B1 C13 . . 112.56(19) ?
N2 B1 N1 . . 104.30(17) ?
C17 B1 N1 . . 112.97(19) ?
C13 B1 N1 . . 108.25(18) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C10 . . . . -179.3(2) ?
B1 N1 C1 C10 . . . . 8.9(4) ?
C4 N1 C1 C2 . . . . 3.0(3) ?
B1 N1 C1 C2 . . . . -168.8(2) ?
N1 C1 C2 C12 . . . . -134.2(2) ?
C10 C1 C2 C12 . . . . 48.0(3) ?
N1 C1 C2 C11 . . . . 104.6(2) ?
C10 C1 C2 C11 . . . . -73.2(3) ?
N1 C1 C2 C3 . . . . -12.4(3) ?
C10 C1 C2 C3 . . . . 169.8(2) ?
C1 C2 C3 C4 . . . . 15.9(2) ?
C12 C2 C3 C4 . . . . 137.1(2) ?
C11 C2 C3 C4 . . . . -98.5(2) ?
C1 N1 C4 C5 . . . . -172.8(2) ?
B1 N1 C4 C5 . . . . -0.7(3) ?
C1 N1 C4 C3 . . . . 8.3(2) ?
B1 N1 C4 C3 . . . . -179.58(19) ?
C2 C3 C4 C5 . . . . 165.8(2) ?
C2 C3 C4 N1 . . . . -15.4(2) ?
N1 C4 C5 C6 . . . . -5.1(3) ?
C3 C4 C5 C6 . . . . 173.6(2) ?
C9 N2 C6 C7 . . . . 1.1(2) ?
B1 N2 C6 C7 . . . . -172.0(2) ?
C9 N2 C6 C5 . . . . -173.9(2) ?
B1 N2 C6 C5 . . . . 13.0(3) ?
C4 C5 C6 N2 . . . . -0.6(3) ?
C4 C5 C6 C7 . . . . -174.3(2) ?
N2 C6 C7 C8 . . . . -1.5(3) ?
C5 C6 C7 C8 . . . . 172.7(2) ?
N2 C6 C7 Br1 . . . . -178.02(16) ?
C5 C6 C7 Br1 . . . . -3.7(4) ?
C6 C7 C8 C9 . . . . 1.3(3) ?
Br1 C7 C8 C9 . . . . 177.59(17) ?
C6 C7 C8 C21 . . . . -177.4(2) ?
Br1 C7 C8 C21 . . . . -1.2(4) ?
C6 N2 C9 C8 . . . . -0.3(3) ?
B1 N2 C9 C8 . . . . 173.0(2) ?
C7 C8 C9 N2 . . . . -0.6(3) ?
C21 C8 C9 N2 . . . . 178.2(2) ?
B1 C13 C14 C15 . . . . 179.9(2) ?
C13 C14 C15 C16 . . . . 179.4(3) ?
B1 C17 C18 C19 . . . . -171.5(2) ?
C17 C18 C19 C20 . . . . 172.7(3) ?
C22 O2 C21 O1 . . . . 2.0(4) ?
C22 O2 C21 C8 . . . . -177.4(2) ?
C9 C8 C21 O1 . . . . 178.9(2) ?
C7 C8 C21 O1 . . . . -2.6(4) ?
C9 C8 C21 O2 . . . . -1.8(3) ?
C7 C8 C21 O2 . . . . 176.7(2) ?
C21 O2 C22 C23 . . . . -92.6(3) ?
C9 N2 B1 C17 . . . . 51.1(3) ?
C6 N2 B1 C17 . . . . -136.9(2) ?
C9 N2 B1 C13 . . . . -72.4(3) ?
C6 N2 B1 C13 . . . . 99.6(2) ?
C9 N2 B1 N1 . . . . 172.0(2) ?
C6 N2 B1 N1 . . . . -16.0(3) ?
C18 C17 B1 N2 . . . . 57.2(3) ?
C18 C17 B1 C13 . . . . 178.8(2) ?
C18 C17 B1 N1 . . . . -58.2(3) ?
C14 C13 B1 N2 . . . . -51.2(3) ?
C14 C13 B1 C17 . . . . -172.5(2) ?
C14 C13 B1 N1 . . . . 61.9(3) ?
C1 N1 B1 N2 . . . . -179.5(2) ?
C4 N1 B1 N2 . . . . 9.7(3) ?
C1 N1 B1 C17 . . . . -61.4(3) ?
C4 N1 B1 C17 . . . . 127.9(2) ?
C1 N1 B1 C13 . . . . 64.0(3) ?
C4 N1 B1 C13 . . . . -106.8(2) ?

