# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1581024'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H37 B Br N2, B Br4, Toluene'
_chemical_formula_sum            'C26 H37 B2 Br5 N2'
_chemical_formula_weight         798.74

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.317(2)
_cell_length_b                   22.811(5)
_cell_length_c                   14.606(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.718(6)
_cell_angle_gamma                90
_cell_volume                     3863.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.37

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    5.216
_shelx_estimated_absorpt_T_min   0.229
_shelx_estimated_absorpt_T_max   0.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2455
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Imus
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 CMOS'
_diffrn_measurement_method       'Omegaφ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            118311
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7600
_reflns_number_gt                6114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 The severely disordered discrete solvent toluene was
 solvent-masked using PLATON/SQUEEZE as suggested by the 
 referee.
 Structure factors included contributions from the .fab file.
 
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+7.0875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7600
_refine_ls_number_parameters     329
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7935(3) 0.55720(17) 0.8244(3) 0.0223(8) Uani 1 1 d . . . . .
Br1 Br 0.90597(4) 0.57038(2) 0.94702(3) 0.03857(11) Uani 1 1 d . . . . .
B2 B 0.3399(4) 0.43916(19) 0.6009(3) 0.0280(9) Uani 1 1 d . . . . .
Br2 Br 0.48406(3) 0.41283(2) 0.57540(3) 0.03914(12) Uani 1 1 d . . . . .
Br3 Br 0.35675(4) 0.42254(2) 0.73992(3) 0.03720(11) Uani 1 1 d . . . . .
Br4 Br 0.31817(4) 0.52607(2) 0.57583(3) 0.03735(11) Uani 1 1 d . . . . .
Br5 Br 0.20592(3) 0.39512(2) 0.51031(3) 0.03999(12) Uani 1 1 d . . . . .
N1 N 0.7012(2) 0.59366(12) 0.77333(19) 0.0207(6) Uani 1 1 d . . . . .
N2 N 0.7883(2) 0.50634(12) 0.7608(2) 0.0226(6) Uani 1 1 d . . . . .
C1 C 0.6408(3) 0.56919(15) 0.6808(3) 0.0232(7) Uani 1 1 d D . . . .
H1A H 0.5569(17) 0.567(2) 0.657(4) 0.072(16) Uiso 1 1 d D . . . .
H1B H 0.636(5) 0.5956(19) 0.625(3) 0.075(17) Uiso 1 1 d D . . . .
C2 C 0.7018(3) 0.51452(15) 0.6762(3) 0.0246(8) Uani 1 1 d D . . . .
H2 H 0.692(4) 0.4860(15) 0.627(2) 0.054(13) Uiso 1 1 d D . . . .
C3 C 0.8618(3) 0.45437(15) 0.7818(2) 0.0243(8) Uani 1 1 d . . . . .
C4 C 0.9667(3) 0.45748(16) 0.7654(3) 0.0294(8) Uani 1 1 d . . . . .
C5 C 1.0370(4) 0.40768(19) 0.7894(3) 0.0392(10) Uani 1 1 d . . . . .
H5 H 1.1091 0.4076 0.7790 0.047 Uiso 1 1 calc R U . . .
C6 C 1.0029(4) 0.35909(19) 0.8276(3) 0.0436(11) Uani 1 1 d . . . . .
H6 H 1.0525 0.3260 0.8445 0.052 Uiso 1 1 calc R U . . .
C7 C 0.8976(4) 0.35736(17) 0.8421(3) 0.0392(10) Uani 1 1 d . . . . .
H7 H 0.8757 0.3230 0.8682 0.047 Uiso 1 1 calc R U . . .
C8 C 0.8232(3) 0.40508(15) 0.8191(3) 0.0291(8) Uani 1 1 d . . . . .
C9 C 0.7088(3) 0.40345(16) 0.8371(3) 0.0347(9) Uani 1 1 d . . . . .
H9 H 0.6552 0.4311 0.7901 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6528(4) 0.34306(18) 0.8202(4) 0.0559(13) Uani 1 1 d . . . . .
H10A H 0.5796 0.3445 0.8328 0.084 Uiso 1 1 calc R U . . .
H10B H 0.6384 0.3311 0.7527 0.084 Uiso 1 1 calc R U . . .
H10C H 0.7044 0.3147 0.8642 0.084 Uiso 1 1 calc R U . . .
C11 C 0.7231(5) 0.4250(2) 0.9400(4) 0.0566(13) Uani 1 1 d . . . . .
H11A H 0.7591 0.4639 0.9500 0.085 Uiso 1 1 calc R U . . .
H11B H 0.6472 0.4274 0.9478 0.085 Uiso 1 1 calc R U . . .
H11C H 0.7720 0.3975 0.9878 0.085 Uiso 1 1 calc R U . . .
C12 C 1.0055(3) 0.51086(18) 0.7237(3) 0.0364(9) Uani 1 1 d . . . . .
H12 H 0.9448 0.5417 0.7127 0.044 Uiso 1 1 calc R U . . .
C13 C 1.1183(4) 0.5354(2) 0.7937(4) 0.0558(13) Uani 1 1 d . . . . .
H13A H 1.1087 0.5446 0.8561 0.084 Uiso 1 1 calc R U . . .
H13B H 1.1796 0.5062 0.8038 0.084 Uiso 1 1 calc R U . . .
H13C H 1.1389 0.5711 0.7661 0.084 Uiso 1 1 calc R U . . .
C14 C 1.0187(4) 0.4961(2) 0.6252(3) 0.0504(12) Uani 1 1 d . . . . .
H14A H 1.0439 0.5311 0.5990 0.076 Uiso 1 1 calc R U . . .
H14B H 1.0762 0.4650 0.6342 0.076 Uiso 1 1 calc R U . . .
H14C H 0.9445 0.4828 0.5796 0.076 Uiso 1 1 calc R U . . .
C15 C 0.6640(3) 0.64835(15) 0.8038(2) 0.0242(8) Uani 1 1 d . . . . .
C16 C 0.7043(4) 0.70120(16) 0.7774(3) 0.0372(9) Uani 1 1 d . . . . .
C17 C 0.6675(4) 0.75270(17) 0.8078(3) 0.0469(11) Uani 1 1 d . . . . .
H17 H 0.6920 0.7892 0.7904 0.056 Uiso 1 1 calc R U . . .
C18 C 0.5966(4) 0.75198(18) 0.8624(3) 0.0446(11) Uani 1 1 d . . . . .
H18 H 0.5731 0.7879 0.8830 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5589(4) 0.69963(18) 0.8880(3) 0.0385(10) Uani 1 1 d . . . . .
H19 H 0.5096 0.7000 0.9259 0.046 Uiso 1 1 calc R U . . .
C20 C 0.5918(3) 0.64605(16) 0.8592(3) 0.0288(8) Uani 1 1 d . . . . .
C21 C 0.5510(4) 0.58927(17) 0.8901(3) 0.0366(9) Uani 1 1 d . . . . .
H21 H 0.5806 0.5563 0.8601 0.044 Uiso 1 1 calc R U . . .
C22 C 0.6017(4) 0.5823(2) 1.0017(3) 0.0488(11) Uani 1 1 d . . . . .
H22A H 0.6860 0.5850 1.0228 0.073 Uiso 1 1 calc R U . . .
H22B H 0.5718 0.6134 1.0328 0.073 Uiso 1 1 calc R U . . .
H22C H 0.5796 0.5440 1.0203 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4203(4) 0.5853(2) 0.8547(3) 0.0498(12) Uani 1 1 d . . . . .
H23A H 0.3971 0.5480 0.8760 0.075 Uiso 1 1 calc R U . . .
H23B H 0.3890 0.6179 0.8818 0.075 Uiso 1 1 calc R U . . .
H23C H 0.3904 0.5874 0.7835 0.075 Uiso 1 1 calc R U . . .
C24 C 0.7903(5) 0.70286(19) 0.7219(4) 0.0567(14) Uani 1 1 d . . . . .
H24 H 0.7994 0.6621 0.7005 0.068 Uiso 1 1 calc R U . . .
C25 C 0.9092(5) 0.7244(3) 0.7884(5) 0.0821(19) Uani 1 1 d . . . . .
H25A H 0.9628 0.7252 0.7518 0.123 Uiso 1 1 calc R U . . .
H25B H 0.9017 0.7640 0.8118 0.123 Uiso 1 1 calc R U . . .
H25C H 0.9387 0.6979 0.8441 0.123 Uiso 1 1 calc R U . . .
C26 C 0.7435(5) 0.7413(2) 0.6311(3) 0.0708(17) Uani 1 1 d . . . . .
H26A H 0.7990 0.7420 0.5964 0.106 Uiso 1 1 calc R U . . .
H26B H 0.6700 0.7252 0.5885 0.106 Uiso 1 1 calc R U . . .
H26C H 0.7314 0.7813 0.6504 0.106 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.403(5) . ?
B1 N2 1.475(5) . ?
B1 Br1 1.882(4) . ?
B2 Br5 2.003(4) . ?
B2 Br4 2.017(4) . ?
B2 Br3 2.007(4) . ?
B2 Br2 2.024(4) . ?
N1 C1 1.419(4) . ?
N1 C15 1.450(4) . ?
N2 C2 1.344(4) . ?
N2 C3 1.460(4) . ?
C1 H1A 0.974(19) . ?
C1 H1B 0.996(19) . ?
C1 C2 1.470(5) . ?
C2 H2 0.946(19) . ?
C3 C4 1.393(5) . ?
C3 C8 1.400(5) . ?
C4 C5 1.399(5) . ?
C4 C12 1.510(6) . ?
C5 C6 1.369(6) . ?
C6 C7 1.384(6) . ?
C7 C8 1.389(5) . ?
C8 C9 1.520(6) . ?
C9 C10 1.523(5) . ?
C9 C11 1.534(6) . ?
C12 C14 1.540(6) . ?
C12 C13 1.526(6) . ?
C15 C16 1.406(5) . ?
C15 C20 1.392(5) . ?
C16 C17 1.385(6) . ?
C16 C24 1.536(6) . ?
C17 C18 1.368(6) . ?
C18 C19 1.377(6) . ?
C19 C20 1.396(5) . ?
C20 C21 1.511(5) . ?
C21 C23 1.519(6) . ?
C21 C22 1.545(6) . ?
C24 C26 1.531(7) . ?
C24 C25 1.540(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 B1 N2 106.0(3) . . ?
N1 B1 Br1 128.0(3) . . ?
N2 B1 Br1 126.0(3) . . ?
Br5 B2 Br4 110.1(2) . . ?
Br5 B2 Br3 110.75(19) . . ?
Br4 B2 Br3 109.3(2) . . ?
Br5 B2 Br2 107.95(19) . . ?
Br4 B2 Br2 109.23(19) . . ?
Br3 B2 Br2 109.4(2) . . ?
B1 N1 C1 110.1(3) . . ?
B1 N1 C15 129.1(3) . . ?
C1 N1 C15 120.8(3) . . ?
C2 N2 C3 123.3(3) . . ?
C2 N2 B1 108.8(3) . . ?
C3 N2 B1 127.9(3) . . ?
H1A C1 H1B 89(4) . . ?
H1A C1 N1 121(3) . . ?
H1B C1 N1 114(3) . . ?
H1A C1 C2 115(3) . . ?
H1B C1 C2 111(3) . . ?
N1 C1 C2 105.4(3) . . ?
H2 C2 N2 117(3) . . ?
H2 C2 C1 133(3) . . ?
N2 C2 C1 109.5(3) . . ?
C4 C3 C8 124.3(3) . . ?
C4 C3 N2 117.9(3) . . ?
C8 C3 N2 117.8(3) . . ?
C5 C4 C3 116.6(4) . . ?
C5 C4 C12 120.2(4) . . ?
C3 C4 C12 123.3(3) . . ?
C6 C5 C4 120.7(4) . . ?
C5 C6 C7 121.1(4) . . ?
C6 C7 C8 121.1(4) . . ?
C3 C8 C7 116.2(4) . . ?
C3 C8 C9 122.9(3) . . ?
C7 C8 C9 120.9(4) . . ?
C10 C9 C8 112.9(3) . . ?
C10 C9 C11 110.2(4) . . ?
C8 C9 C11 110.8(3) . . ?
C14 C12 C4 110.4(4) . . ?
C14 C12 C13 110.3(3) . . ?
C4 C12 C13 111.5(3) . . ?
C16 C15 C20 123.1(3) . . ?
C16 C15 N1 118.4(3) . . ?
C20 C15 N1 118.5(3) . . ?
C15 C16 C17 117.1(4) . . ?
C15 C16 C24 122.4(3) . . ?
C17 C16 C24 120.4(4) . . ?
C18 C17 C16 121.3(4) . . ?
C17 C18 C19 120.5(4) . . ?
C20 C19 C18 121.3(4) . . ?
C19 C20 C15 116.7(3) . . ?
C19 C20 C21 120.1(3) . . ?
C15 C20 C21 123.2(3) . . ?
C23 C21 C20 111.7(4) . . ?
C23 C21 C22 111.0(3) . . ?
C20 C21 C22 110.3(3) . . ?
C16 C24 C26 110.2(4) . . ?
C16 C24 C25 110.7(4) . . ?
C26 C24 C25 111.3(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
N2 B1 N1 C1 -1.5(4) . . . . ?
Br1 B1 N1 C1 176.4(3) . . . . ?
N2 B1 N1 C15 177.5(3) . . . . ?
Br1 B1 N1 C15 -4.6(5) . . . . ?
N1 B1 N2 C2 3.0(4) . . . . ?
Br1 B1 N2 C2 -175.0(3) . . . . ?
N1 B1 N2 C3 -176.9(3) . . . . ?
Br1 B1 N2 C3 5.2(5) . . . . ?
B1 N1 C1 H1A 133(4) . . . . ?
C15 N1 C1 H1A -46(4) . . . . ?
B1 N1 C1 H1B -123(3) . . . . ?
C15 N1 C1 H1B 58(3) . . . . ?
B1 N1 C1 C2 -0.4(4) . . . . ?
C15 N1 C1 C2 -179.5(3) . . . . ?
C3 N2 C2 H2 -4(3) . . . . ?
B1 N2 C2 H2 176(3) . . . . ?
C3 N2 C2 C1 176.6(3) . . . . ?
B1 N2 C2 C1 -3.3(4) . . . . ?
H1A C1 C2 H2 47(5) . . . . ?
H1B C1 C2 H2 -53(5) . . . . ?
N1 C1 C2 H2 -177(4) . . . . ?
H1A C1 C2 N2 -134(3) . . . . ?
H1B C1 C2 N2 126(3) . . . . ?
N1 C1 C2 N2 2.4(4) . . . . ?
C2 N2 C3 C4 95.6(4) . . . . ?
B1 N2 C3 C4 -84.6(4) . . . . ?
C2 N2 C3 C8 -85.8(4) . . . . ?
B1 N2 C3 C8 94.0(4) . . . . ?
C8 C3 C4 C5 -0.7(5) . . . . ?
N2 C3 C4 C5 177.9(3) . . . . ?
C8 C3 C4 C12 179.0(3) . . . . ?
N2 C3 C4 C12 -2.4(5) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C12 C4 C5 C6 179.7(4) . . . . ?
C4 C5 C6 C7 1.2(6) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
C4 C3 C8 C7 1.2(5) . . . . ?
N2 C3 C8 C7 -177.3(3) . . . . ?
C4 C3 C8 C9 179.3(3) . . . . ?
N2 C3 C8 C9 0.7(5) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C6 C7 C8 C9 -178.7(4) . . . . ?
C3 C8 C9 C10 146.7(4) . . . . ?
C7 C8 C9 C10 -35.4(5) . . . . ?
C3 C8 C9 C11 -89.2(4) . . . . ?
C7 C8 C9 C11 88.8(4) . . . . ?
C5 C4 C12 C14 62.8(5) . . . . ?
C3 C4 C12 C14 -116.9(4) . . . . ?
C5 C4 C12 C13 -60.2(5) . . . . ?
C3 C4 C12 C13 120.2(4) . . . . ?
B1 N1 C15 C16 94.7(4) . . . . ?
C1 N1 C15 C16 -86.5(4) . . . . ?
B1 N1 C15 C20 -84.1(5) . . . . ?
C1 N1 C15 C20 94.8(4) . . . . ?
C20 C15 C16 C17 -1.0(6) . . . . ?
N1 C15 C16 C17 -179.8(4) . . . . ?
C20 C15 C16 C24 175.8(4) . . . . ?
N1 C15 C16 C24 -2.9(6) . . . . ?
C15 C16 C17 C18 1.0(7) . . . . ?
C24 C16 C17 C18 -175.9(4) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C18 C19 C20 0.1(7) . . . . ?
C18 C19 C20 C15 -0.1(6) . . . . ?
C18 C19 C20 C21 178.7(4) . . . . ?
C16 C15 C20 C19 0.6(6) . . . . ?
N1 C15 C20 C19 179.3(3) . . . . ?
C16 C15 C20 C21 -178.2(4) . . . . ?
N1 C15 C20 C21 0.5(5) . . . . ?
C19 C20 C21 C23 59.1(5) . . . . ?
C15 C20 C21 C23 -122.2(4) . . . . ?
C19 C20 C21 C22 -64.8(5) . . . . ?
C15 C20 C21 C22 113.9(4) . . . . ?
C15 C16 C24 C26 127.1(4) . . . . ?
C17 C16 C24 C26 -56.1(6) . . . . ?
C15 C16 C24 C25 -109.3(5) . . . . ?
C17 C16 C24 C25 67.5(6) . . . . ?

_refine_diff_density_max         0.960
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.089



####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1581025'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H36 B2 Br4 N2'
_chemical_formula_weight         717.82

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.6037(12)
_cell_length_b                   17.1792(11)
_cell_length_c                   37.549(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12645.5(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9452
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.19

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             5696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    5.108
_shelx_estimated_absorpt_T_min   0.207
_shelx_estimated_absorpt_T_max   0.362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1543
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Imus
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 CMOS'
_diffrn_measurement_method       'Omegaφ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            107342
_diffrn_reflns_av_unetI/netI     0.0898
_diffrn_reflns_av_R_equivalents  0.1521
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.078
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11448
_reflns_number_gt                5934
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
  the high Rint factor (0.1521) might be caused by the weak 
  reflections at high 2theta angles.

 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0744P)²+51.2858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11448
_refine_ls_number_parameters     625
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1618
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.6364(5) 0.7497(5) 0.4755(2) 0.039(2) Uani 1 1 d . . . . .
B2 B 0.4525(5) 0.7260(6) 0.5118(3) 0.047(2) Uani 1 1 d . . . . .
Br1 Br 0.72923(4) 0.77620(7) 0.48114(3) 0.0754(4) Uani 1 1 d . . . . .
Br2 Br 0.40031(5) 0.63502(6) 0.49229(3) 0.0700(3) Uani 1 1 d . . . . .
Br3 Br 0.41025(5) 0.82693(6) 0.49183(3) 0.0803(4) Uani 1 1 d . . . . .
Br4 Br 0.44668(6) 0.72790(8) 0.56398(3) 0.0890(4) Uani 1 1 d . . . . .
N1 N 0.5858(3) 0.7483(4) 0.50525(15) 0.0365(15) Uani 1 1 d . . . . .
N2 N 0.6024(3) 0.7289(4) 0.44546(15) 0.0366(15) Uani 1 1 d . . . . .
C1 C 0.5246(4) 0.7290(4) 0.49311(19) 0.0349(17) Uani 1 1 d . . . . .
C2 C 0.5324(4) 0.7110(5) 0.45445(19) 0.042(2) Uani 1 1 d D . . . .
H2A H 0.499(3) 0.740(4) 0.4403(16) 0.045 Uiso 1 1 d D U . . .
H2B H 0.518(4) 0.6570(18) 0.4490(18) 0.045 Uiso 1 1 d D U . . .
C3 C 0.6253(3) 0.7185(5) 0.4091(2) 0.041(2) Uani 1 1 d . . . . .
C4 C 0.6569(4) 0.6479(5) 0.4001(2) 0.049(2) Uani 1 1 d . . . . .
C5 C 0.6762(4) 0.6403(6) 0.3646(3) 0.064(3) Uani 1 1 d . . . . .
H5 H 0.6973 0.5945 0.3574 0.077 Uiso 1 1 calc R U . . .
C6 C 0.6654(5) 0.6974(8) 0.3400(3) 0.074(3) Uani 1 1 d . . . . .
H6 H 0.6783 0.6900 0.3164 0.089 Uiso 1 1 calc R U . . .
C7 C 0.6358(5) 0.7650(6) 0.3502(2) 0.059(2) Uani 1 1 d . . . . .
H7 H 0.6294 0.8039 0.3333 0.070 Uiso 1 1 calc R U . . .
C8 C 0.6147(4) 0.7782(5) 0.3850(2) 0.041(2) Uani 1 1 d . . . . .
C9 C 0.5850(4) 0.8556(5) 0.3956(2) 0.052(2) Uani 1 1 d . . . . .
H9 H 0.5677 0.8493 0.4199 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5240(6) 0.8793(7) 0.3727(3) 0.095(4) Uani 1 1 d . . . . .
H10A H 0.4914 0.8376 0.3722 0.142 Uiso 1 1 calc R U . . .
H10B H 0.5031 0.9250 0.3825 0.142 Uiso 1 1 calc R U . . .
H10C H 0.5391 0.8901 0.3488 0.142 Uiso 1 1 calc R U . . .
C11 C 0.6375(6) 0.9192(6) 0.3970(4) 0.104(4) Uani 1 1 d . . . . .
H11A H 0.6159 0.9671 0.4039 0.157 Uiso 1 1 calc R U . . .
H11B H 0.6719 0.9059 0.4142 0.157 Uiso 1 1 calc R U . . .
H11C H 0.6581 0.9252 0.3740 0.157 Uiso 1 1 calc R U . . .
C12 C 0.6679(5) 0.5839(6) 0.4266(3) 0.072(3) Uani 1 1 d . . . . .
H12 H 0.6515 0.6024 0.4497 0.087 Uiso 1 1 calc R U . . .
C13 C 0.7446(7) 0.5653(9) 0.4305(4) 0.143(6) Uani 1 1 d . . . . .
H13A H 0.7689 0.6120 0.4365 0.215 Uiso 1 1 calc R U . . .
H13B H 0.7508 0.5274 0.4490 0.215 Uiso 1 1 calc R U . . .
H13C H 0.7617 0.5450 0.4084 0.215 Uiso 1 1 calc R U . . .
C14 C 0.6278(8) 0.5124(7) 0.4172(4) 0.133(5) Uani 1 1 d . . . . .
H14A H 0.6360 0.4726 0.4346 0.200 Uiso 1 1 calc R U . . .
H14B H 0.5801 0.5247 0.4167 0.200 Uiso 1 1 calc R U . . .
H14C H 0.6417 0.4940 0.3941 0.200 Uiso 1 1 calc R U . . .
C15 C 0.6042(4) 0.7612(5) 0.5426(2) 0.0410(19) Uani 1 1 d . . . . .
C16 C 0.6223(4) 0.6956(6) 0.5623(2) 0.053(2) Uani 1 1 d . . . . .
C17 C 0.6434(5) 0.7095(7) 0.5969(2) 0.069(3) Uani 1 1 d . . . . .
H17 H 0.6563 0.6678 0.6112 0.083 Uiso 1 1 calc R U . . .
C18 C 0.6456(6) 0.7835(8) 0.6106(3) 0.086(4) Uani 1 1 d . . . . .
H18 H 0.6587 0.7909 0.6342 0.103 Uiso 1 1 calc R U . . .
C19 C 0.6291(6) 0.8463(7) 0.5903(3) 0.079(3) Uani 1 1 d . . . . .
H19 H 0.6322 0.8960 0.6000 0.095 Uiso 1 1 calc R U . . .
C20 C 0.6075(5) 0.8373(6) 0.5551(2) 0.058(2) Uani 1 1 d . . . . .
C21 C 0.5876(6) 0.9072(6) 0.5337(3) 0.076(3) Uani 1 1 d . . . . .
H21 H 0.5705 0.8888 0.5107 0.091 Uiso 1 1 calc R U . . .
C22 C 0.5312(6) 0.9549(7) 0.5512(3) 0.097(4) Uani 1 1 d . . . . .
H22A H 0.5204 0.9988 0.5364 0.146 Uiso 1 1 calc R U . . .
H22B H 0.4913 0.9231 0.5540 0.146 Uiso 1 1 calc R U . . .
H22C H 0.5463 0.9728 0.5741 0.146 Uiso 1 1 calc R U . . .
C23 C 0.6487(7) 0.9603(7) 0.5265(4) 0.132(5) Uani 1 1 d . . . . .
H23A H 0.6341 1.0044 0.5128 0.198 Uiso 1 1 calc R U . . .
H23B H 0.6674 0.9779 0.5487 0.198 Uiso 1 1 calc R U . . .
H23C H 0.6828 0.9321 0.5135 0.198 Uiso 1 1 calc R U . . .
C24 C 0.6210(5) 0.6146(5) 0.5482(2) 0.063(3) Uani 1 1 d . . . . .
H24 H 0.5991 0.6164 0.5247 0.076 Uiso 1 1 calc R U . . .
C25 C 0.5803(8) 0.5590(7) 0.5709(4) 0.144(6) Uani 1 1 d . . . . .
H25A H 0.5814 0.5080 0.5604 0.216 Uiso 1 1 calc R U . . .
H25B H 0.5997 0.5569 0.5943 0.216 Uiso 1 1 calc R U . . .
H25C H 0.5340 0.5766 0.5724 0.216 Uiso 1 1 calc R U . . .
C26 C 0.6905(7) 0.5802(8) 0.5432(4) 0.133(5) Uani 1 1 d . . . . .
H26A H 0.6863 0.5282 0.5340 0.200 Uiso 1 1 calc R U . . .
H26B H 0.7160 0.6114 0.5266 0.200 Uiso 1 1 calc R U . . .
H26C H 0.7139 0.5789 0.5656 0.200 Uiso 1 1 calc R U . . .
B3 B 0.3583(4) 0.7461(5) 0.7649(2) 0.040(2) Uani 1 1 d . . . . .
B4 B 0.5337(5) 0.6905(8) 0.7254(3) 0.069(3) Uani 1 1 d . . . . .
Br5 Br 0.26706(4) 0.78063(8) 0.75968(2) 0.0814(4) Uani 1 1 d . . . . .
Br6 Br 0.52905(6) 0.66174(8) 0.67417(3) 0.0829(4) Uani 1 1 d . . . . .
Br7 Br 0.58281(6) 0.79542(9) 0.73191(4) 0.1086(5) Uani 1 1 d . . . . .
Br8 Br 0.58499(7) 0.60911(10) 0.75223(3) 0.1225(6) Uani 1 1 d . . . . .
N3 N 0.4027(3) 0.7253(4) 0.73419(15) 0.0356(15) Uani 1 1 d . . . . .
N4 N 0.3944(3) 0.7358(4) 0.79491(15) 0.0379(15) Uani 1 1 d . . . . .
C27 C 0.4635(4) 0.7075(5) 0.7457(2) 0.0405(19) Uani 1 1 d . . . . .
C28 C 0.4626(4) 0.7088(5) 0.7851(2) 0.042(2) Uani 1 1 d D . . . .
H28A H 0.500(3) 0.738(4) 0.7967(17) 0.045 Uiso 1 1 d D U . . .
H28B H 0.467(4) 0.656(2) 0.7952(18) 0.045 Uiso 1 1 d D U . . .
C29 C 0.3754(4) 0.7395(5) 0.8322(2) 0.043(2) Uani 1 1 d . . . . .
C30 C 0.3906(4) 0.8053(6) 0.8515(2) 0.050(2) Uani 1 1 d . . . . .
C31 C 0.3722(5) 0.8057(7) 0.8870(2) 0.069(3) Uani 1 1 d . . . . .
H31 H 0.3816 0.8493 0.9008 0.083 Uiso 1 1 calc R U . . .
C32 C 0.3405(5) 0.7431(9) 0.9021(3) 0.086(4) Uani 1 1 d . . . . .
H32 H 0.3279 0.7449 0.9260 0.103 Uiso 1 1 calc R U . . .
C33 C 0.3271(5) 0.6786(7) 0.8828(3) 0.076(3) Uani 1 1 d . . . . .
H33 H 0.3066 0.6362 0.8939 0.091 Uiso 1 1 calc R U . . .
C34 C 0.3431(4) 0.6740(6) 0.8470(2) 0.054(2) Uani 1 1 d . . . . .
C35 C 0.3248(5) 0.6029(6) 0.8258(3) 0.074(3) Uani 1 1 d . . . . .
H35 H 0.3435 0.6097 0.8018 0.088 Uiso 1 1 calc R U . . .
C36 C 0.2481(6) 0.5946(8) 0.8222(4) 0.120(5) Uani 1 1 d . . . . .
H36A H 0.2378 0.5488 0.8086 0.179 Uiso 1 1 calc R U . . .
H36B H 0.2280 0.5903 0.8454 0.179 Uiso 1 1 calc R U . . .
H36C H 0.2300 0.6395 0.8103 0.179 Uiso 1 1 calc R U . . .
C37 C 0.3549(9) 0.5284(8) 0.8411(5) 0.167(8) Uani 1 1 d . . . . .
H37A H 0.3416 0.4850 0.8266 0.250 Uiso 1 1 calc R U . . .
H37B H 0.4038 0.5324 0.8415 0.250 Uiso 1 1 calc R U . . .
H37C H 0.3384 0.5209 0.8650 0.250 Uiso 1 1 calc R U . . .
C38 C 0.4224(5) 0.8753(5) 0.8348(2) 0.065(3) Uani 1 1 d . . . . .
H38 H 0.4382 0.8607 0.8110 0.077 Uiso 1 1 calc R U . . .
C39 C 0.4841(5) 0.9048(7) 0.8560(3) 0.100(4) Uani 1 1 d . . . . .
H39A H 0.5029 0.9498 0.8444 0.151 Uiso 1 1 calc R U . . .
H39B H 0.4700 0.9184 0.8797 0.151 Uiso 1 1 calc R U . . .
H39C H 0.5181 0.8646 0.8571 0.151 Uiso 1 1 calc R U . . .
C40 C 0.3715(7) 0.9418(7) 0.8307(4) 0.124(5) Uani 1 1 d . . . . .
H40A H 0.3938 0.9857 0.8200 0.186 Uiso 1 1 calc R U . . .
H40B H 0.3343 0.9253 0.8159 0.186 Uiso 1 1 calc R U . . .
H40C H 0.3544 0.9564 0.8537 0.186 Uiso 1 1 calc R U . . .
C41 C 0.3778(4) 0.7195(5) 0.6975(2) 0.044(2) Uani 1 1 d . . . . .
C42 C 0.3834(4) 0.7816(5) 0.6744(2) 0.049(2) Uani 1 1 d . . . . .
C43 C 0.3544(5) 0.7731(7) 0.6407(2) 0.072(3) Uani 1 1 d . . . . .
H43 H 0.3575 0.8134 0.6242 0.086 Uiso 1 1 calc R U . . .
C44 C 0.3215(5) 0.7061(9) 0.6318(3) 0.086(4) Uani 1 1 d . . . . .
H44 H 0.3033 0.7007 0.6091 0.103 Uiso 1 1 calc R U . . .
C45 C 0.3149(5) 0.6474(8) 0.6555(3) 0.083(4) Uani 1 1 d . . . . .
H45 H 0.2912 0.6027 0.6489 0.099 Uiso 1 1 calc R U . . .
C46 C 0.3426(4) 0.6524(6) 0.6893(2) 0.059(3) Uani 1 1 d . . . . .
C47 C 0.3346(6) 0.5851(7) 0.7153(3) 0.082(3) Uani 1 1 d . . . . .
H47 H 0.3421 0.6065 0.7392 0.099 Uiso 1 1 calc R U . . .
C48 C 0.2627(7) 0.5502(9) 0.7153(4) 0.147(6) Uani 1 1 d . . . . .
H48A H 0.2606 0.5081 0.7321 0.220 Uiso 1 1 calc R U . . .
H48B H 0.2303 0.5895 0.7219 0.220 Uiso 1 1 calc R U . . .
H48C H 0.2520 0.5310 0.6920 0.220 Uiso 1 1 calc R U . . .
C49 C 0.3898(8) 0.5227(8) 0.7095(4) 0.147(6) Uani 1 1 d . . . . .
H49A H 0.3833 0.4811 0.7263 0.221 Uiso 1 1 calc R U . . .
H49B H 0.3864 0.5026 0.6858 0.221 Uiso 1 1 calc R U . . .
H49C H 0.4340 0.5454 0.7130 0.221 Uiso 1 1 calc R U . . .
C50 C 0.4186(5) 0.8561(6) 0.6843(3) 0.069(3) Uani 1 1 d . . . . .
H50 H 0.4423 0.8476 0.7069 0.083 Uiso 1 1 calc R U . . .
C51 C 0.3662(7) 0.9214(7) 0.6899(3) 0.114(5) Uani 1 1 d . . . . .
H51A H 0.3895 0.9686 0.6962 0.172 Uiso 1 1 calc R U . . .
H51B H 0.3409 0.9294 0.6684 0.172 Uiso 1 1 calc R U . . .
H51C H 0.3356 0.9071 0.7087 0.172 Uiso 1 1 calc R U . . .
C52 C 0.4718(6) 0.8812(7) 0.6567(3) 0.106(4) Uani 1 1 d . . . . .
H52A H 0.4928 0.9290 0.6642 0.159 Uiso 1 1 calc R U . . .
H52B H 0.5060 0.8415 0.6545 0.159 Uiso 1 1 calc R U . . .
H52C H 0.4500 0.8889 0.6341 0.159 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N2 1.359(10) . ?
B1 N1 1.492(10) . ?
B1 Br1 1.888(9) . ?
B2 C1 1.579(11) . ?
B2 Br4 1.963(10) . ?
B2 Br2 2.006(10) . ?
B2 Br3 2.063(10) . ?
N1 C1 1.325(9) . ?
N1 C15 1.466(9) . ?
N2 C3 1.448(9) . ?
N2 C2 1.445(9) . ?
C1 C2 1.493(10) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.99(2) . ?
C3 C8 1.385(11) . ?
C3 C4 1.403(11) . ?
C4 C5 1.392(12) . ?
C4 C12 1.497(12) . ?
C5 C6 1.364(13) . ?
C6 C7 1.352(13) . ?
C7 C8 1.388(11) . ?
C8 C9 1.505(11) . ?
C9 C11 1.501(12) . ?
C9 C10 1.529(12) . ?
C12 C14 1.501(16) . ?
C12 C13 1.544(15) . ?
C15 C20 1.391(12) . ?
C15 C16 1.394(12) . ?
C16 C17 1.385(12) . ?
C16 C24 1.489(12) . ?
C17 C18 1.372(14) . ?
C18 C19 1.359(15) . ?
C19 C20 1.396(12) . ?
C20 C21 1.497(13) . ?
C21 C23 1.530(15) . ?
C21 C22 1.524(14) . ?
C24 C26 1.498(15) . ?
C24 C25 1.508(15) . ?
B3 N4 1.343(10) . ?
B3 N3 1.488(11) . ?
B3 Br5 1.894(9) . ?
B4 C27 1.600(12) . ?
B4 Br6 1.987(11) . ?
B4 Br8 1.995(11) . ?
B4 Br7 2.058(14) . ?
N3 C27 1.305(9) . ?
N3 C41 1.464(9) . ?
N4 C29 1.452(9) . ?
N4 C28 1.462(9) . ?
C27 C28 1.483(11) . ?
C28 H28B 0.98(2) . ?
C28 H28A 0.99(2) . ?
C29 C30 1.373(11) . ?
C29 C34 1.405(12) . ?
C30 C31 1.381(12) . ?
C30 C38 1.492(12) . ?
C31 C32 1.367(15) . ?
C32 C33 1.348(15) . ?
C33 C34 1.385(12) . ?
C34 C35 1.501(13) . ?
C35 C36 1.515(14) . ?
C35 C37 1.522(16) . ?
C38 C40 1.524(14) . ?
C38 C39 1.534(13) . ?
C41 C46 1.378(12) . ?
C41 C42 1.381(11) . ?
C42 C43 1.395(12) . ?
C42 C50 1.501(13) . ?
C43 C44 1.360(15) . ?
C44 C45 1.352(15) . ?
C45 C46 1.385(13) . ?
C46 C47 1.520(14) . ?
C47 C49 1.538(16) . ?
C47 C48 1.532(14) . ?
C50 C51 1.535(14) . ?
C50 C52 1.531(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 B1 N1 106.9(7) . . ?
N2 B1 Br1 128.9(6) . . ?
N1 B1 Br1 124.1(6) . . ?
C1 B2 Br4 119.7(6) . . ?
C1 B2 Br2 108.7(6) . . ?
Br4 B2 Br2 110.4(5) . . ?
C1 B2 Br3 99.8(6) . . ?
Br4 B2 Br3 109.0(4) . . ?
Br2 B2 Br3 108.5(5) . . ?
C1 N1 C15 126.2(6) . . ?
C1 N1 B1 110.4(6) . . ?
C15 N1 B1 123.3(6) . . ?
B1 N2 C3 131.5(6) . . ?
B1 N2 C2 109.1(6) . . ?
C3 N2 C2 119.3(6) . . ?
N1 C1 C2 107.1(6) . . ?
N1 C1 B2 131.7(7) . . ?
C2 C1 B2 121.1(7) . . ?
H2A C2 H2B 101(6) . . ?
H2A C2 N2 113(4) . . ?
H2B C2 N2 115(4) . . ?
H2A C2 C1 111(4) . . ?
H2B C2 C1 112(4) . . ?
N2 C2 C1 106.3(6) . . ?
C8 C3 C4 123.3(7) . . ?
C8 C3 N2 118.6(7) . . ?
C4 C3 N2 118.1(7) . . ?
C5 C4 C3 115.5(8) . . ?
C5 C4 C12 121.9(9) . . ?
C3 C4 C12 122.5(7) . . ?
C6 C5 C4 122.6(9) . . ?
C7 C6 C5 119.5(9) . . ?
C6 C7 C8 122.3(9) . . ?
C7 C8 C3 116.8(8) . . ?
C7 C8 C9 120.5(8) . . ?
C3 C8 C9 122.7(7) . . ?
C11 C9 C8 112.9(8) . . ?
C11 C9 C10 111.3(9) . . ?
C8 C9 C10 112.9(7) . . ?
C14 C12 C4 111.7(9) . . ?
C14 C12 C13 111.2(11) . . ?
C4 C12 C13 110.8(10) . . ?
C20 C15 C16 124.7(7) . . ?
C20 C15 N1 118.5(7) . . ?
C16 C15 N1 116.6(7) . . ?
C17 C16 C15 115.7(9) . . ?
C17 C16 C24 120.1(9) . . ?
C15 C16 C24 124.2(7) . . ?
C18 C17 C16 121.4(9) . . ?
C19 C18 C17 121.2(9) . . ?
C18 C19 C20 121.0(10) . . ?
C19 C20 C15 116.0(9) . . ?
C19 C20 C21 119.9(9) . . ?
C15 C20 C21 124.1(8) . . ?
C20 C21 C23 111.7(10) . . ?
C20 C21 C22 112.9(9) . . ?
C23 C21 C22 108.8(9) . . ?
C16 C24 C26 113.4(9) . . ?
C16 C24 C25 113.5(9) . . ?
C26 C24 C25 107.6(10) . . ?
N4 B3 N3 108.1(7) . . ?
N4 B3 Br5 128.8(7) . . ?
N3 B3 Br5 123.2(6) . . ?
C27 B4 Br6 117.8(7) . . ?
C27 B4 Br8 108.7(7) . . ?
Br6 B4 Br8 109.8(6) . . ?
C27 B4 Br7 100.7(7) . . ?
Br6 B4 Br7 110.8(6) . . ?
Br8 B4 Br7 108.5(5) . . ?
C27 N3 C41 126.8(6) . . ?
C27 N3 B3 109.6(6) . . ?
C41 N3 B3 123.3(6) . . ?
B3 N4 C29 132.0(6) . . ?
B3 N4 C28 108.3(6) . . ?
C29 N4 C28 119.4(6) . . ?
N3 C27 C28 108.4(6) . . ?
N3 C27 B4 132.2(7) . . ?
C28 C27 B4 119.3(7) . . ?
H28B C28 H28A 104(6) . . ?
H28B C28 N4 106(4) . . ?
H28A C28 N4 114(4) . . ?
H28B C28 C27 112(4) . . ?
H28A C28 C27 116(4) . . ?
N4 C28 C27 105.4(6) . . ?
C30 C29 C34 123.3(8) . . ?
C30 C29 N4 119.2(8) . . ?
C34 C29 N4 117.4(7) . . ?
C31 C30 C29 117.1(9) . . ?
C31 C30 C38 120.6(9) . . ?
C29 C30 C38 122.3(8) . . ?
C30 C31 C32 121.1(10) . . ?
C33 C32 C31 120.8(9) . . ?
C32 C33 C34 121.5(10) . . ?
C33 C34 C29 116.1(9) . . ?
C33 C34 C35 120.4(9) . . ?
C29 C34 C35 123.5(8) . . ?
C34 C35 C36 111.2(9) . . ?
C34 C35 C37 113.1(9) . . ?
C36 C35 C37 109.9(11) . . ?
C30 C38 C40 112.0(9) . . ?
C30 C38 C39 112.2(8) . . ?
C40 C38 C39 108.7(9) . . ?
C46 C41 C42 123.1(8) . . ?
C46 C41 N3 115.7(8) . . ?
C42 C41 N3 120.9(8) . . ?
C43 C42 C41 117.3(9) . . ?
C43 C42 C50 120.1(9) . . ?
C41 C42 C50 122.7(8) . . ?
C44 C43 C42 120.3(10) . . ?
C45 C44 C43 121.1(10) . . ?
C44 C45 C46 121.3(11) . . ?
C45 C46 C41 116.9(10) . . ?
C45 C46 C47 120.0(10) . . ?
C41 C46 C47 123.0(8) . . ?
C46 C47 C49 111.6(9) . . ?
C46 C47 C48 113.2(11) . . ?
C49 C47 C48 112.0(11) . . ?
C42 C50 C51 110.5(9) . . ?
C42 C50 C52 112.7(9) . . ?
C51 C50 C52 110.1(9) . . ?

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
N2 B1 N1 C1 -1.1(9) . . . . ?
Br1 B1 N1 C1 178.9(6) . . . . ?
N2 B1 N1 C15 174.7(7) . . . . ?
Br1 B1 N1 C15 -5.3(11) . . . . ?
N1 B1 N2 C3 -178.3(7) . . . . ?
Br1 B1 N2 C3 1.7(14) . . . . ?
N1 B1 N2 C2 -2.3(9) . . . . ?
Br1 B1 N2 C2 177.7(7) . . . . ?
C15 N1 C1 C2 -171.9(7) . . . . ?
B1 N1 C1 C2 3.9(9) . . . . ?
C15 N1 C1 B2 10.4(13) . . . . ?
B1 N1 C1 B2 -173.9(8) . . . . ?
Br4 B2 C1 N1 -15.6(13) . . . . ?
Br2 B2 C1 N1 -143.6(7) . . . . ?
Br3 B2 C1 N1 103.0(9) . . . . ?
Br4 B2 C1 C2 166.9(6) . . . . ?
Br2 B2 C1 C2 38.9(10) . . . . ?
Br3 B2 C1 C2 -74.5(8) . . . . ?
B1 N2 C2 H2A 126(5) . . . . ?
C3 N2 C2 H2A -57(5) . . . . ?
B1 N2 C2 H2B -119(5) . . . . ?
C3 N2 C2 H2B 57(5) . . . . ?
B1 N2 C2 C1 4.5(9) . . . . ?
C3 N2 C2 C1 -178.9(7) . . . . ?
N1 C1 C2 H2A -128(5) . . . . ?
B2 C1 C2 H2A 50(5) . . . . ?
N1 C1 C2 H2B 120(5) . . . . ?
B2 C1 C2 H2B -62(5) . . . . ?
N1 C1 C2 N2 -5.1(9) . . . . ?
B2 C1 C2 N2 172.9(7) . . . . ?
B1 N2 C3 C8 -99.2(10) . . . . ?
C2 N2 C3 C8 85.1(9) . . . . ?
B1 N2 C3 C4 81.2(11) . . . . ?
C2 N2 C3 C4 -94.5(9) . . . . ?
C8 C3 C4 C5 -1.2(12) . . . . ?
N2 C3 C4 C5 178.3(7) . . . . ?
C8 C3 C4 C12 -179.9(8) . . . . ?
N2 C3 C4 C12 -0.4(12) . . . . ?
C3 C4 C5 C6 0.0(13) . . . . ?
C12 C4 C5 C6 178.7(9) . . . . ?
C4 C5 C6 C7 1.1(15) . . . . ?
C5 C6 C7 C8 -1.1(15) . . . . ?
C6 C7 C8 C3 0.0(13) . . . . ?
C6 C7 C8 C9 177.1(8) . . . . ?
C4 C3 C8 C7 1.2(11) . . . . ?
N2 C3 C8 C7 -178.3(7) . . . . ?
C4 C3 C8 C9 -175.8(7) . . . . ?
N2 C3 C8 C9 4.7(11) . . . . ?
C7 C8 C9 C11 -71.8(11) . . . . ?
C3 C8 C9 C11 105.1(10) . . . . ?
C7 C8 C9 C10 55.5(11) . . . . ?
C3 C8 C9 C10 -127.6(9) . . . . ?
C5 C4 C12 C14 -63.3(13) . . . . ?
C3 C4 C12 C14 115.3(11) . . . . ?
C5 C4 C12 C13 61.3(13) . . . . ?
C3 C4 C12 C13 -120.1(10) . . . . ?
C1 N1 C15 C20 -99.1(9) . . . . ?
B1 N1 C15 C20 85.7(9) . . . . ?
C1 N1 C15 C16 85.7(10) . . . . ?
B1 N1 C15 C16 -89.5(9) . . . . ?
C20 C15 C16 C17 1.5(13) . . . . ?
N1 C15 C16 C17 176.4(7) . . . . ?
C20 C15 C16 C24 -177.7(9) . . . . ?
N1 C15 C16 C24 -2.8(12) . . . . ?
C15 C16 C17 C18 0.3(14) . . . . ?
C24 C16 C17 C18 179.5(10) . . . . ?
C16 C17 C18 C19 -1.9(17) . . . . ?
C17 C18 C19 C20 1.7(18) . . . . ?
C18 C19 C20 C15 0.0(15) . . . . ?
C18 C19 C20 C21 178.1(10) . . . . ?
C16 C15 C20 C19 -1.7(13) . . . . ?
N1 C15 C20 C19 -176.5(8) . . . . ?
C16 C15 C20 C21 -179.8(9) . . . . ?
N1 C15 C20 C21 5.5(13) . . . . ?
C19 C20 C21 C23 66.5(13) . . . . ?
C15 C20 C21 C23 -115.5(11) . . . . ?
C19 C20 C21 C22 -56.5(13) . . . . ?
C15 C20 C21 C22 121.5(10) . . . . ?
C17 C16 C24 C26 -69.0(13) . . . . ?
C15 C16 C24 C26 110.2(11) . . . . ?
C17 C16 C24 C25 54.1(13) . . . . ?
C15 C16 C24 C25 -126.7(11) . . . . ?
N4 B3 N3 C27 -3.2(9) . . . . ?
Br5 B3 N3 C27 176.8(6) . . . . ?
N4 B3 N3 C41 171.5(7) . . . . ?
Br5 B3 N3 C41 -8.4(11) . . . . ?
N3 B3 N4 C29 -173.1(8) . . . . ?
Br5 B3 N4 C29 6.9(14) . . . . ?
N3 B3 N4 C28 0.4(9) . . . . ?
Br5 B3 N4 C28 -179.7(7) . . . . ?
C41 N3 C27 C28 -170.0(7) . . . . ?
B3 N3 C27 C28 4.5(9) . . . . ?
C41 N3 C27 B4 13.7(15) . . . . ?
B3 N3 C27 B4 -171.8(10) . . . . ?
Br6 B4 C27 N3 -19.7(15) . . . . ?
Br8 B4 C27 N3 -145.3(8) . . . . ?
Br7 B4 C27 N3 100.8(10) . . . . ?
Br6 B4 C27 C28 164.2(7) . . . . ?
Br8 B4 C27 C28 38.6(11) . . . . ?
Br7 B4 C27 C28 -75.3(9) . . . . ?
B3 N4 C28 H28B -116(4) . . . . ?
C29 N4 C28 H28B 58(5) . . . . ?
B3 N4 C28 H28A 130(5) . . . . ?
C29 N4 C28 H28A -55(5) . . . . ?
B3 N4 C28 C27 2.2(9) . . . . ?
C29 N4 C28 C27 176.6(7) . . . . ?
N3 C27 C28 H28B 110(5) . . . . ?
B4 C27 C28 H28B -73(5) . . . . ?
N3 C27 C28 H28A -131(5) . . . . ?
B4 C27 C28 H28A 46(5) . . . . ?
N3 C27 C28 N4 -4.3(9) . . . . ?
B4 C27 C28 N4 172.6(8) . . . . ?
B3 N4 C29 C30 -100.6(10) . . . . ?
C28 N4 C29 C30 86.5(9) . . . . ?
B3 N4 C29 C34 80.5(11) . . . . ?
C28 N4 C29 C34 -92.4(9) . . . . ?
C34 C29 C30 C31 -0.5(12) . . . . ?
N4 C29 C30 C31 -179.3(7) . . . . ?
C34 C29 C30 C38 -177.4(8) . . . . ?
N4 C29 C30 C38 3.8(11) . . . . ?
C29 C30 C31 C32 0.2(14) . . . . ?
C38 C30 C31 C32 177.1(9) . . . . ?
C30 C31 C32 C33 0.9(16) . . . . ?
C31 C32 C33 C34 -1.8(17) . . . . ?
C32 C33 C34 C29 1.5(15) . . . . ?
C32 C33 C34 C35 -177.3(10) . . . . ?
C30 C29 C34 C33 -0.3(12) . . . . ?
N4 C29 C34 C33 178.5(7) . . . . ?
C30 C29 C34 C35 178.4(8) . . . . ?
N4 C29 C34 C35 -2.8(12) . . . . ?
C33 C34 C35 C36 66.9(13) . . . . ?
C29 C34 C35 C36 -111.7(10) . . . . ?
C33 C34 C35 C37 -57.2(14) . . . . ?
C29 C34 C35 C37 124.1(12) . . . . ?
C31 C30 C38 C40 -70.4(12) . . . . ?
C29 C30 C38 C40 106.4(10) . . . . ?
C31 C30 C38 C39 52.3(12) . . . . ?
C29 C30 C38 C39 -131.0(9) . . . . ?
C27 N3 C41 C46 95.9(9) . . . . ?
B3 N3 C41 C46 -78.0(10) . . . . ?
C27 N3 C41 C42 -90.8(10) . . . . ?
B3 N3 C41 C42 95.4(9) . . . . ?
C46 C41 C42 C43 -3.0(12) . . . . ?
N3 C41 C42 C43 -175.9(7) . . . . ?
C46 C41 C42 C50 176.6(8) . . . . ?
N3 C41 C42 C50 3.8(12) . . . . ?
C41 C42 C43 C44 0.7(13) . . . . ?
C50 C42 C43 C44 -178.9(9) . . . . ?
C42 C43 C44 C45 1.5(16) . . . . ?
C43 C44 C45 C46 -1.5(16) . . . . ?
C44 C45 C46 C41 -0.7(14) . . . . ?
C44 C45 C46 C47 -179.7(10) . . . . ?
C42 C41 C46 C45 3.0(12) . . . . ?
N3 C41 C46 C45 176.2(7) . . . . ?
C42 C41 C46 C47 -178.1(8) . . . . ?
N3 C41 C46 C47 -4.8(12) . . . . ?
C45 C46 C47 C49 84.3(13) . . . . ?
C41 C46 C47 C49 -94.6(12) . . . . ?
C45 C46 C47 C48 -43.0(14) . . . . ?
C41 C46 C47 C48 138.0(10) . . . . ?
C43 C42 C50 C51 72.3(11) . . . . ?
C41 C42 C50 C51 -107.3(10) . . . . ?
C43 C42 C50 C52 -51.3(12) . . . . ?
C41 C42 C50 C52 129.1(9) . . . . ?

_refine_diff_density_max         1.955
_refine_diff_density_min         -1.494
_refine_diff_density_rms         0.102

####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1581026'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2017-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H36 B2 Br I3 N2'
_chemical_formula_weight         858.80

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'
I I -0.4742 1.8119 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.2369(6)
_cell_length_b                   14.6825(7)
_cell_length_c                   18.0610(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3245.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.29

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             1640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    4.137
_shelx_estimated_absorpt_T_min   0.288
_shelx_estimated_absorpt_T_max   0.576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2577
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Imus
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 CMOS'
_diffrn_measurement_method       'Omegaφ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            104369
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         27.879
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7743
_reflns_number_gt                6716
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     1.000
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+3.1668P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.052(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7743
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.6685(5) 0.5230(5) 0.6890(4) 0.0364(13) Uani 1 1 d . . . . .
B2 B 0.8917(6) 0.6110(5) 0.5526(4) 0.0481(16) Uani 1 1 d . . . . .
Br1 Br 0.60285(6) 0.51828(5) 0.78422(3) 0.05548(18) Uani 1 1 d . . . . .
I1 I 1.00519(4) 0.71133(4) 0.60026(3) 0.07314(18) Uani 1 1 d . . . . .
I2 I 0.81084(6) 0.67337(5) 0.45429(3) 0.07738(19) Uani 1 1 d . . . . .
I3 I 0.98917(5) 0.48637(4) 0.51921(4) 0.0839(2) Uani 1 1 d . . . . .
N1 N 0.7628(4) 0.5843(3) 0.6701(2) 0.0328(9) Uani 1 1 d . . . . .
N2 N 0.6446(4) 0.4739(4) 0.6285(3) 0.0407(11) Uani 1 1 d . . . . .
C1 C 0.7933(5) 0.5692(4) 0.6015(3) 0.0398(12) Uani 1 1 d . . . . .
C2 C 0.7170(6) 0.5015(5) 0.5682(3) 0.0534(18) Uani 1 1 d . . . . .
H2A H 0.6756 0.5288 0.5282 0.064 Uiso 1 1 calc R U . . .
H2B H 0.7570 0.4495 0.5490 0.064 Uiso 1 1 calc R U . . .
C3 C 0.5674(5) 0.4012(4) 0.6161(3) 0.0373(12) Uani 1 1 d . . . . .
C4 C 0.6032(6) 0.3109(5) 0.6249(3) 0.0469(14) Uani 1 1 d . . . . .
C5 C 0.5283(7) 0.2430(5) 0.6119(5) 0.0597(18) Uani 1 1 d . . . . .
H5A H 0.5503 0.1826 0.6159 0.072 Uiso 1 1 calc R U . . .
C6 C 0.4230(7) 0.2617(5) 0.5934(5) 0.066(2) Uani 1 1 d . . . . .
H6A H 0.3738 0.2144 0.5853 0.079 Uiso 1 1 calc R U . . .
C7 C 0.3895(6) 0.3503(5) 0.5865(4) 0.0559(17) Uani 1 1 d . . . . .
H7A H 0.3171 0.3623 0.5743 0.067 Uiso 1 1 calc R U . . .
C8 C 0.4610(5) 0.4227(4) 0.5974(3) 0.0411(13) Uani 1 1 d . . . . .
C9 C 0.4196(6) 0.5191(5) 0.5880(4) 0.0545(16) Uani 1 1 d . . . . .
H9A H 0.4811 0.5606 0.5965 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3762(14) 0.5369(9) 0.5121(7) 0.118(5) Uani 1 1 d . . . . .
H10A H 0.3511 0.5987 0.5090 0.177 Uiso 1 1 calc R U . . .
H10B H 0.4331 0.5272 0.4763 0.177 Uiso 1 1 calc R U . . .
H10C H 0.3166 0.4963 0.5021 0.177 Uiso 1 1 calc R U . . .
C11 C 0.3312(10) 0.5413(7) 0.6446(7) 0.096(3) Uani 1 1 d . . . . .
H11A H 0.3065 0.6027 0.6373 0.144 Uiso 1 1 calc R U . . .
H11B H 0.2709 0.5001 0.6384 0.144 Uiso 1 1 calc R U . . .
H11C H 0.3604 0.5350 0.6936 0.144 Uiso 1 1 calc R U . . .
C12 C 0.7214(6) 0.2882(6) 0.6469(5) 0.0633(19) Uani 1 1 d . . . . .
H12A H 0.7621 0.3456 0.6483 0.076 Uiso 1 1 calc R U . . .
C13 C 0.7251(10) 0.2479(10) 0.7233(7) 0.106(4) Uani 1 1 d . . . . .
H13A H 0.7995 0.2342 0.7362 0.160 Uiso 1 1 calc R U . . .
H13B H 0.6958 0.2908 0.7582 0.160 Uiso 1 1 calc R U . . .
H13C H 0.6825 0.1930 0.7245 0.160 Uiso 1 1 calc R U . . .
C14 C 0.7758(11) 0.2274(12) 0.5891(8) 0.131(6) Uani 1 1 d . . . . .
H14A H 0.8494 0.2143 0.6041 0.196 Uiso 1 1 calc R U . . .
H14B H 0.7356 0.1715 0.5847 0.196 Uiso 1 1 calc R U . . .
H14C H 0.7766 0.2581 0.5422 0.196 Uiso 1 1 calc R U . . .
C15 C 0.8072(5) 0.6491(4) 0.7223(3) 0.0340(11) Uani 1 1 d . . . . .
C16 C 0.8834(5) 0.6181(5) 0.7739(4) 0.0459(14) Uani 1 1 d . . . . .
C17 C 0.9172(7) 0.6804(6) 0.8269(4) 0.065(2) Uani 1 1 d . . . . .
H17A H 0.9675 0.6626 0.8627 0.077 Uiso 1 1 calc R U . . .
C18 C 0.8776(7) 0.7683(6) 0.8273(5) 0.069(2) Uani 1 1 d . . . . .
H18A H 0.9013 0.8091 0.8633 0.082 Uiso 1 1 calc R U . . .
C19 C 0.8042(7) 0.7957(5) 0.7754(5) 0.0593(18) Uani 1 1 d . . . . .
H19A H 0.7792 0.8555 0.7766 0.071 Uiso 1 1 calc R U . . .
C20 C 0.7659(5) 0.7383(4) 0.7215(4) 0.0401(12) Uani 1 1 d . . . . .
C21 C 0.6838(6) 0.7707(5) 0.6641(4) 0.0535(16) Uani 1 1 d . . . . .
H21A H 0.6884 0.7296 0.6215 0.064 Uiso 1 1 calc R U . . .
C22 C 0.7059(11) 0.8661(9) 0.6369(8) 0.113(5) Uani 1 1 d . . . . .
H22A H 0.6517 0.8828 0.6010 0.170 Uiso 1 1 calc R U . . .
H22B H 0.7029 0.9077 0.6779 0.170 Uiso 1 1 calc R U . . .
H22C H 0.7770 0.8685 0.6146 0.170 Uiso 1 1 calc R U . . .
C23 C 0.5675(8) 0.7648(9) 0.6952(7) 0.099(4) Uani 1 1 d . . . . .
H23A H 0.5538 0.7040 0.7124 0.148 Uiso 1 1 calc R U . . .
H23B H 0.5598 0.8068 0.7356 0.148 Uiso 1 1 calc R U . . .
H23C H 0.5161 0.7799 0.6570 0.148 Uiso 1 1 calc R U . . .
C24 C 0.9301(8) 0.5228(6) 0.7724(6) 0.083(3) Uani 1 1 d . . . . .
H24A H 0.8964 0.4890 0.7316 0.099 Uiso 1 1 calc R U . . .
C25 C 0.9000(13) 0.4752(12) 0.8468(13) 0.186(10) Uani 1 1 d . . . . .
H25A H 0.9289 0.4144 0.8471 0.279 Uiso 1 1 calc R U . . .
H25B H 0.9306 0.5089 0.8874 0.279 Uiso 1 1 calc R U . . .
H25C H 0.8220 0.4728 0.8519 0.279 Uiso 1 1 calc R U . . .
C26 C 1.0533(11) 0.5249(9) 0.7609(9) 0.118(5) Uani 1 1 d . . . . .
H26A H 1.0811 0.4638 0.7601 0.177 Uiso 1 1 calc R U . . .
H26B H 1.0695 0.5542 0.7147 0.177 Uiso 1 1 calc R U . . .
H26C H 1.0870 0.5581 0.8006 0.177 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N2 1.342(8) . ?
B1 N1 1.503(7) . ?
B1 Br1 1.899(6) . ?
B2 C1 1.615(9) . ?
B2 I1 2.200(8) . ?
B2 I2 2.229(8) . ?
B2 I3 2.265(8) . ?
N1 C1 1.311(8) . ?
N1 C15 1.446(7) . ?
N2 C3 1.443(7) . ?
N2 C2 1.461(8) . ?
C1 C2 1.491(8) . ?
C3 C8 1.382(9) . ?
C3 C4 1.406(10) . ?
C4 C5 1.373(10) . ?
C4 C12 1.536(11) . ?
C5 C6 1.359(12) . ?
C6 C7 1.369(12) . ?
C7 C8 1.391(8) . ?
C8 C9 1.513(10) . ?
C9 C11 1.524(13) . ?
C9 C10 1.493(13) . ?
C12 C13 1.503(15) . ?
C12 C14 1.526(14) . ?
C15 C16 1.395(8) . ?
C15 C20 1.404(8) . ?
C16 C17 1.387(10) . ?
C16 C24 1.512(11) . ?
C17 C18 1.378(13) . ?
C18 C19 1.358(12) . ?
C19 C20 1.372(10) . ?
C20 C21 1.519(10) . ?
C21 C22 1.509(13) . ?
C21 C23 1.532(13) . ?
C24 C26 1.522(17) . ?
C24 C25 1.56(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 B1 N1 107.7(5) . . ?
N2 B1 Br1 128.7(4) . . ?
N1 B1 Br1 123.6(4) . . ?
C1 B2 I1 120.7(5) . . ?
C1 B2 I2 105.1(5) . . ?
I1 B2 I2 108.5(3) . . ?
C1 B2 I3 103.4(4) . . ?
I1 B2 I3 108.2(3) . . ?
I2 B2 I3 110.7(3) . . ?
C1 N1 C15 128.3(5) . . ?
C1 N1 B1 109.4(5) . . ?
C15 N1 B1 122.2(5) . . ?
B1 N2 C3 131.8(5) . . ?
B1 N2 C2 109.0(5) . . ?
C3 N2 C2 119.2(5) . . ?
N1 C1 C2 108.4(5) . . ?
N1 C1 B2 131.7(5) . . ?
C2 C1 B2 119.9(5) . . ?
N2 C2 C1 105.3(5) . . ?
C8 C3 C4 122.4(5) . . ?
C8 C3 N2 119.1(5) . . ?
C4 C3 N2 118.5(5) . . ?
C5 C4 C3 117.2(6) . . ?
C5 C4 C12 121.0(7) . . ?
C3 C4 C12 121.8(6) . . ?
C6 C5 C4 121.9(7) . . ?
C5 C6 C7 119.8(7) . . ?
C8 C7 C6 121.7(7) . . ?
C3 C8 C7 116.9(6) . . ?
C3 C8 C9 123.8(5) . . ?
C7 C8 C9 119.3(6) . . ?
C8 C9 C11 111.2(6) . . ?
C8 C9 C10 112.7(7) . . ?
C11 C9 C10 109.0(9) . . ?
C4 C12 C13 110.6(7) . . ?
C4 C12 C14 111.2(8) . . ?
C13 C12 C14 112.6(10) . . ?
C16 C15 C20 123.5(6) . . ?
C16 C15 N1 118.2(5) . . ?
C20 C15 N1 118.1(5) . . ?
C17 C16 C15 116.4(6) . . ?
C17 C16 C24 120.7(7) . . ?
C15 C16 C24 122.9(6) . . ?
C18 C17 C16 121.1(7) . . ?
C19 C18 C17 120.4(7) . . ?
C20 C19 C18 122.3(7) . . ?
C19 C20 C15 116.2(6) . . ?
C19 C20 C21 121.2(6) . . ?
C15 C20 C21 122.5(6) . . ?
C22 C21 C20 113.3(8) . . ?
C22 C21 C23 109.7(8) . . ?
C20 C21 C23 110.3(6) . . ?
C16 C24 C26 111.0(9) . . ?
C16 C24 C25 108.1(11) . . ?
C26 C24 C25 111.2(10) . . ?

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
N2 B1 N1 C1 -1.3(7) . . . . ?
Br1 B1 N1 C1 177.0(5) . . . . ?
N2 B1 N1 C15 177.8(5) . . . . ?
Br1 B1 N1 C15 -3.9(8) . . . . ?
N1 B1 N2 C3 175.5(6) . . . . ?
Br1 B1 N2 C3 -2.8(11) . . . . ?
N1 B1 N2 C2 -1.8(7) . . . . ?
Br1 B1 N2 C2 180.0(6) . . . . ?
C15 N1 C1 C2 -175.3(6) . . . . ?
B1 N1 C1 C2 3.7(7) . . . . ?
C15 N1 C1 B2 3.8(11) . . . . ?
B1 N1 C1 B2 -177.2(7) . . . . ?
I1 B2 C1 N1 0.8(10) . . . . ?
I2 B2 C1 N1 -122.0(7) . . . . ?
I3 B2 C1 N1 121.8(7) . . . . ?
I1 B2 C1 C2 179.8(5) . . . . ?
I2 B2 C1 C2 57.0(7) . . . . ?
I3 B2 C1 C2 -59.2(7) . . . . ?
B1 N2 C2 C1 3.9(8) . . . . ?
C3 N2 C2 C1 -173.8(6) . . . . ?
N1 C1 C2 N2 -4.7(8) . . . . ?
B2 C1 C2 N2 176.1(6) . . . . ?
B1 N2 C3 C8 86.3(8) . . . . ?
C2 N2 C3 C8 -96.7(7) . . . . ?
B1 N2 C3 C4 -92.7(8) . . . . ?
C2 N2 C3 C4 84.4(8) . . . . ?
C8 C3 C4 C5 1.9(9) . . . . ?
N2 C3 C4 C5 -179.2(6) . . . . ?
C8 C3 C4 C12 -179.1(6) . . . . ?
N2 C3 C4 C12 -0.2(9) . . . . ?
C3 C4 C5 C6 -1.9(12) . . . . ?
C12 C4 C5 C6 179.1(8) . . . . ?
C4 C5 C6 C7 0.7(14) . . . . ?
C5 C6 C7 C8 0.6(13) . . . . ?
C4 C3 C8 C7 -0.7(9) . . . . ?
N2 C3 C8 C7 -179.6(6) . . . . ?
C4 C3 C8 C9 179.6(6) . . . . ?
N2 C3 C8 C9 0.7(9) . . . . ?
C6 C7 C8 C3 -0.6(11) . . . . ?
C6 C7 C8 C9 179.1(8) . . . . ?
C3 C8 C9 C11 -117.1(8) . . . . ?
C7 C8 C9 C11 63.3(10) . . . . ?
C3 C8 C9 C10 120.1(9) . . . . ?
C7 C8 C9 C10 -59.5(11) . . . . ?
C5 C4 C12 C13 -68.9(11) . . . . ?
C3 C4 C12 C13 112.1(10) . . . . ?
C5 C4 C12 C14 56.9(12) . . . . ?
C3 C4 C12 C14 -122.1(10) . . . . ?
C1 N1 C15 C16 -97.7(7) . . . . ?
B1 N1 C15 C16 83.4(7) . . . . ?
C1 N1 C15 C20 86.4(7) . . . . ?
B1 N1 C15 C20 -92.4(7) . . . . ?
C20 C15 C16 C17 0.7(10) . . . . ?
N1 C15 C16 C17 -174.9(6) . . . . ?
C20 C15 C16 C24 -177.8(8) . . . . ?
N1 C15 C16 C24 6.6(10) . . . . ?
C15 C16 C17 C18 -0.5(12) . . . . ?
C24 C16 C17 C18 178.0(9) . . . . ?
C16 C17 C18 C19 -0.1(14) . . . . ?
C17 C18 C19 C20 0.6(14) . . . . ?
C18 C19 C20 C15 -0.4(11) . . . . ?
C18 C19 C20 C21 -180.0(8) . . . . ?
C16 C15 C20 C19 -0.2(9) . . . . ?
N1 C15 C20 C19 175.3(6) . . . . ?
C16 C15 C20 C21 179.3(6) . . . . ?
N1 C15 C20 C21 -5.1(9) . . . . ?
C19 C20 C21 C22 39.6(11) . . . . ?
C15 C20 C21 C22 -139.9(8) . . . . ?
C19 C20 C21 C23 -83.8(10) . . . . ?
C15 C20 C21 C23 96.7(9) . . . . ?
C17 C16 C24 C26 -60.3(13) . . . . ?
C15 C16 C24 C26 118.1(10) . . . . ?
C17 C16 C24 C25 61.8(12) . . . . ?
C15 C16 C24 C25 -119.8(10) . . . . ?

_refine_diff_density_max         0.851
_refine_diff_density_min         -1.603
_refine_diff_density_rms         0.142

