# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

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

data_compound4
_database_code_depnum_ccdc_archive 'CCDC 1946582'
loop_
_audit_author_name
_audit_author_address
'Hans Georg Stammler'
;University of Bielefeld
Germany
;
_audit_update_record             
;
2019-08-12 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;






_audit_creation_date             2019-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H26 B2 Br2 N4, 2(C6 H6)'
_chemical_formula_sum            'C44 H38 B2 Br2 N4'
_chemical_formula_weight         804.22
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   12.8327(2)
_cell_length_b                   5.35020(10)
_cell_length_c                   27.5244(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.6528(8)
_cell_angle_gamma                90
_cell_volume                     1863.00(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    49977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_shelx_estimated_absorpt_T_max   0.809
_shelx_estimated_absorpt_T_min   0.597
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  0.8090
_exptl_absorpt_correction_T_min  0.5968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       column
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            42904
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.980
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3703
_reflns_number_total             4254
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect, Bruker AXS, 2004'
_computing_data_reduction        
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.8498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0628
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br 0.09190(2) 0.54569(3) 0.43072(2) 0.02188(6) Uani 1 1 d . . . . .
N1 N 0.28873(9) 0.3814(3) 0.49560(5) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.32123(10) 0.6660(3) 0.43696(4) 0.0178(3) Uani 1 1 d . . . . .
B1 B 0.24101(14) 0.5305(4) 0.45531(7) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.39961(12) 0.4228(3) 0.50172(5) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.41951(12) 0.6000(3) 0.46649(5) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.52073(12) 0.6945(3) 0.46506(5) 0.0175(3) Uani 1 1 d . . . . .
C4 C 0.54197(12) 0.9240(3) 0.43606(6) 0.0196(3) Uani 1 1 d . . . . .
H4A H 0.601969 1.016345 0.454354 0.029 Uiso 1 1 calc GR . . . .
H4B H 0.479205 1.031376 0.431042 0.029 Uiso 1 1 calc GR . . . .
H4C H 0.558476 0.872891 0.404014 0.029 Uiso 1 1 calc GR . . . .
C5 C 0.23634(12) 0.2829(3) 0.53380(6) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.25181(13) 0.3969(4) 0.57986(6) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.297718 0.536600 0.586372 0.028 Uiso 1 1 calc R . . . .
C7 C 0.19924(14) 0.3038(4) 0.61625(6) 0.0294(4) Uani 1 1 d . . . . .
H7 H 0.209433 0.380194 0.647847 0.035 Uiso 1 1 calc R . . . .
C8 C 0.13221(14) 0.1007(4) 0.60679(7) 0.0317(4) Uani 1 1 d . . . . .
H8 H 0.097108 0.037020 0.631937 0.038 Uiso 1 1 calc R . . . .
C9 C 0.11633(14) -0.0097(4) 0.56064(7) 0.0296(4) Uani 1 1 d . . . . .
H9 H 0.069686 -0.148077 0.554075 0.035 Uiso 1 1 calc R . . . .
C10 C 0.16837(13) 0.0811(3) 0.52389(6) 0.0235(4) Uani 1 1 d . . . . .
H10 H 0.157440 0.005393 0.492219 0.028 Uiso 1 1 calc R . . . .
C11 C 0.31127(12) 0.7977(3) 0.39108(5) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.24395(13) 1.0025(3) 0.38277(6) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.204023 1.052708 0.407203 0.026 Uiso 1 1 calc R . . . .
C13 C 0.23513(13) 1.1336(4) 0.33873(6) 0.0259(4) Uani 1 1 d . . . . .
H13 H 0.188585 1.272529 0.332931 0.031 Uiso 1 1 calc R . . . .
C14 C 0.29418(14) 1.0622(4) 0.30315(6) 0.0276(4) Uani 1 1 d . . . . .
H14 H 0.289226 1.153966 0.273296 0.033 Uiso 1 1 calc R . . . .
C15 C 0.36039(13) 0.8564(4) 0.31141(6) 0.0254(4) Uani 1 1 d . . . . .
H15 H 0.400889 0.807614 0.287102 0.030 Uiso 1 1 calc R . . . .
C16 C 0.36803(13) 0.7211(3) 0.35484(6) 0.0219(3) Uani 1 1 d . . . . .
H16 H 0.411757 0.576971 0.359832 0.026 Uiso 1 1 calc R . . . .
C17 C 0.14353(15) 0.3517(4) 0.80026(7) 0.0356(4) Uani 1 1 d . . . . .
H17 H 0.190508 0.353906 0.830851 0.043 Uiso 1 1 calc R . . . .
C18 C 0.06997(14) 0.1640(4) 0.79030(7) 0.0322(4) Uani 1 1 d . . . . .
H18 H 0.066838 0.035752 0.813878 0.039 Uiso 1 1 calc R . . . .
C19 C 0.00034(15) 0.1612(4) 0.74601(7) 0.0353(4) Uani 1 1 d . . . . .
H19 H -0.050490 0.031291 0.739246 0.042 Uiso 1 1 calc R . . . .
C20 C 0.00493(18) 0.3474(4) 0.71171(7) 0.0427(5) Uani 1 1 d . . . . .
H20 H -0.043062 0.346798 0.681411 0.051 Uiso 1 1 calc R . . . .
C21 C 0.0794(2) 0.5341(4) 0.72161(9) 0.0504(7) Uani 1 1 d . . . . .
H21 H 0.082968 0.661881 0.697969 0.060 Uiso 1 1 calc R . . . .
C22 C 0.1494(2) 0.5364(4) 0.76605(9) 0.0463(6) Uani 1 1 d . . . . .
H22 H 0.200878 0.664872 0.772752 0.056 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 1.9214(17) . ?
N1 B1 1.419(2) . ?
N1 C1 1.4218(19) . ?
N1 C5 1.4398(19) . ?
N2 B1 1.419(2) . ?
N2 C2 1.4256(19) . ?
N2 C11 1.433(2) . ?
C1 C2 1.410(2) . ?
C1 C3 1.401(2) 3_666 ?
C2 C3 1.401(2) . ?
C3 C4 1.514(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.391(2) . ?
C5 C10 1.386(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C11 C16 1.392(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.374(3) . ?
C17 C22 1.376(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(4) . ?
C22 H22 0.9500 . ?

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
N1 C1 C2 N2 -1.67(17) . . . . ?
N1 C1 C2 C3 175.41(14) . . . . ?
N1 C5 C6 C7 178.70(15) . . . . ?
N1 C5 C10 C9 -178.65(15) . . . . ?
N2 C2 C3 C1 -177.26(15) . . . 3_666 ?
N2 C2 C3 C4 10.9(3) . . . . ?
N2 C11 C12 C13 178.96(15) . . . . ?
N2 C11 C16 C15 -177.61(15) . . . . ?
B1 N1 C1 C2 1.53(17) . . . . ?
B1 N1 C1 C3 -175.97(16) . . . 3_666 ?
B1 N1 C5 C6 -102.71(19) . . . . ?
B1 N1 C5 C10 75.1(2) . . . . ?
B1 N2 C2 C1 1.15(17) . . . . ?
B1 N2 C2 C3 -175.67(16) . . . . ?
B1 N2 C11 C12 64.1(2) . . . . ?
B1 N2 C11 C16 -115.60(18) . . . . ?
C1 N1 B1 Br1 179.75(12) . . . . ?
C1 N1 B1 N2 -0.81(18) . . . . ?
C1 N1 C5 C6 53.2(2) . . . . ?
C1 N1 C5 C10 -128.91(16) . . . . ?
C1 C2 C3 C1 6.3(2) . . . 3_666 ?
C1 C2 C3 C4 -165.52(15) . . . . ?
C2 N2 B1 Br1 179.23(12) . . . . ?
C2 N2 B1 N1 -0.21(18) . . . . ?
C2 N2 C11 C12 -131.58(16) . . . . ?
C2 N2 C11 C16 48.7(2) . . . . ?
C3 C1 C2 N2 175.96(14) 3_666 . . . ?
C3 C1 C2 C3 -7.0(3) 3_666 . . . ?
C5 N1 B1 Br1 -21.1(2) . . . . ?
C5 N1 B1 N2 158.32(15) . . . . ?
C5 N1 C1 C2 -158.19(15) . . . . ?
C5 N1 C1 C3 24.3(2) . . . 3_666 ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C10 C5 C6 C7 0.9(2) . . . . ?
C11 N2 B1 Br1 -14.3(2) . . . . ?
C11 N2 B1 N1 166.30(14) . . . . ?
C11 N2 C2 C1 -165.81(14) . . . . ?
C11 N2 C2 C3 17.4(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C11 C16 C15 2.7(2) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -2.1(3) . . . . ?
C16 C11 C12 C13 -1.4(2) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C17 C22 C21 0.9(3) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C22 C17 C18 C19 -0.8(3) . . . . ?


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 N1 C1 107.30(13) . . ?
B1 N1 C5 125.69(13) . . ?
C1 N1 C5 123.44(12) . . ?
B1 N2 C2 107.19(13) . . ?
B1 N2 C11 127.00(13) . . ?
C2 N2 C11 124.33(12) . . ?
N1 B1 Br1 124.95(12) . . ?
N1 B1 N2 108.75(13) . . ?
N2 B1 Br1 126.29(13) . . ?
C2 C1 N1 108.43(13) . . ?
C3 C1 N1 127.89(14) 3_666 . ?
C3 C1 C2 123.63(14) 3_666 . ?
C1 C2 N2 108.29(13) . . ?
C3 C2 N2 129.08(14) . . ?
C3 C2 C1 122.55(14) . . ?
C1 C3 C2 113.50(14) 3_666 . ?
C1 C3 C4 122.10(14) 3_666 . ?
C2 C3 C4 123.88(14) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 119.50(15) . . ?
C10 C5 N1 119.80(14) . . ?
C10 C5 C6 120.67(15) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.15(17) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.49(17) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.94(16) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.25(18) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 119.49(17) . . ?
C5 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 N2 119.58(14) . . ?
C12 C11 C16 119.98(15) . . ?
C16 C11 N2 120.44(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.95(15) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.16(17) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.66(16) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.59(16) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.61(16) . . ?
C15 C16 H16 120.2 . . ?
C18 C17 H17 119.9 . . ?
C18 C17 C22 120.2(2) . . ?
C22 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.24(19) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.6(2) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound6
_database_code_depnum_ccdc_archive 'CCDC 1946583'
loop_
_audit_author_name
_audit_author_address
'Hans Georg Stammler'
;University of Bielefeld
Germany
;
_audit_update_record             
;
2019-08-12 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;





_audit_creation_date             2019-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
  
;
_chemical_formula_moiety         'C36 H40 B Br2 N2, B Br4, C H2 Cl2'
_chemical_formula_sum            'C37 H42 B2 Br6 Cl2 N2'
_chemical_formula_weight         1086.70
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   13.8103(2)
_cell_length_b                   11.39990(10)
_cell_length_c                   26.6226(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.3790(7)
_cell_angle_gamma                90
_cell_volume                     4187.74(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    65620
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_shelx_estimated_absorpt_T_max   0.433
_shelx_estimated_absorpt_T_min   0.384
_exptl_absorpt_coefficient_mu    5.909
_exptl_absorpt_correction_T_max  0.4333
_exptl_absorpt_correction_T_min  0.3845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
  
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            81751
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7777
_reflns_number_total             9576
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect, Bruker AXS, 2004'
_computing_data_reduction        
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.945
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         9576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.5666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0724
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22), C31(H31), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br 0.75668(2) 0.40756(2) 0.23091(2) 0.02159(7) Uani 1 1 d . . . . .
Br2 Br 0.73470(2) 0.23647(2) 0.32636(2) 0.02162(7) Uani 1 1 d . . . . .
Br3 Br 0.88753(2) -0.02428(3) 0.54709(2) 0.02693(7) Uani 1 1 d . . . . .
Br4 Br 0.65386(2) 0.02865(2) 0.53022(2) 0.02736(7) Uani 1 1 d . . . . .
Br5 Br 0.73764(2) -0.08264(3) 0.63711(2) 0.02853(8) Uani 1 1 d . . . . .
Br6 Br 0.73332(2) -0.24443(2) 0.53377(2) 0.02237(7) Uani 1 1 d . . . . .
N1 N 0.81673(14) 0.48055(18) 0.33458(7) 0.0148(4) Uani 1 1 d . . . . .
N2 N 0.64336(14) 0.47670(17) 0.31786(7) 0.0139(4) Uani 1 1 d . . . . .
B1 B 0.7372(2) 0.4017(2) 0.30483(10) 0.0172(6) Uani 1 1 d . . . . .
B2 B 0.7535(2) -0.0813(3) 0.56211(10) 0.0201(6) Uani 1 1 d . . . . .
C1 C 0.77673(18) 0.5754(2) 0.35002(8) 0.0157(5) Uani 1 1 d . . . . .
C2 C 0.67028(17) 0.5731(2) 0.33968(8) 0.0154(5) Uani 1 1 d . . . . .
C3 C 0.62892(18) 0.6785(2) 0.35968(8) 0.0163(5) Uani 1 1 d . . . . .
C4 C 0.71006(18) 0.7418(2) 0.38029(8) 0.0164(5) Uani 1 1 d . . . . .
C5 C 0.80076(18) 0.6833(2) 0.37617(8) 0.0171(5) Uani 1 1 d . . . . .
C6 C 0.53675(19) 0.7236(2) 0.36272(9) 0.0197(5) Uani 1 1 d . . . . .
H6 H 0.481769 0.681794 0.349684 0.024 Uiso 1 1 calc R . . . .
C7 C 0.5269(2) 0.8341(2) 0.38587(9) 0.0227(6) Uani 1 1 d . . . . .
H7 H 0.463938 0.866744 0.388271 0.027 Uiso 1 1 calc R . . . .
C8 C 0.6058(2) 0.8963(2) 0.40513(9) 0.0225(6) Uani 1 1 d . . . . .
H8 H 0.595917 0.970604 0.420282 0.027 Uiso 1 1 calc R . . . .
C9 C 0.70096(19) 0.8515(2) 0.40270(8) 0.0191(5) Uani 1 1 d . . . . .
C10 C 0.7890(2) 0.9034(2) 0.42196(9) 0.0231(6) Uani 1 1 d . . . . .
H10 H 0.787316 0.978585 0.437302 0.028 Uiso 1 1 calc R . . . .
C11 C 0.8758(2) 0.8463(2) 0.41864(9) 0.0230(6) Uani 1 1 d . . . . .
H11 H 0.932755 0.883420 0.432052 0.028 Uiso 1 1 calc R . . . .
C12 C 0.88424(19) 0.7353(2) 0.39627(9) 0.0205(6) Uani 1 1 d . . . . .
H12 H 0.945274 0.697176 0.394986 0.025 Uiso 1 1 calc R . . . .
C13 C 0.91916(17) 0.4560(2) 0.34696(9) 0.0153(5) Uani 1 1 d . . . . .
C14 C 0.98943(18) 0.4986(2) 0.31582(9) 0.0169(5) Uani 1 1 d . . . . .
C15 C 1.08592(19) 0.4752(2) 0.33023(9) 0.0203(5) Uani 1 1 d . . . . .
H15 H 1.136047 0.502415 0.309789 0.024 Uiso 1 1 calc R . . . .
C16 C 1.10990(19) 0.4134(2) 0.37358(9) 0.0236(6) Uani 1 1 d . . . . .
H16 H 1.176001 0.397503 0.382313 0.028 Uiso 1 1 calc R . . . .
C17 C 1.03832(19) 0.3745(2) 0.40441(10) 0.0229(6) Uani 1 1 d . . . . .
H17 H 1.056133 0.332308 0.434154 0.028 Uiso 1 1 calc R . . . .
C18 C 0.94018(18) 0.3960(2) 0.39263(9) 0.0186(5) Uani 1 1 d . . . . .
C19 C 0.96713(19) 0.5706(2) 0.26833(9) 0.0194(5) Uani 1 1 d . . . . .
H19 H 0.895122 0.576564 0.263416 0.023 Uiso 1 1 calc R . . . .
C20 C 1.0079(2) 0.6947(2) 0.27386(10) 0.0262(6) Uani 1 1 d . . . . .
H20A H 0.983401 0.731140 0.304146 0.039 Uiso 1 1 calc GR . . . .
H20B H 0.987726 0.741309 0.244327 0.039 Uiso 1 1 calc GR . . . .
H20C H 1.078861 0.691203 0.276654 0.039 Uiso 1 1 calc GR . . . .
C21 C 1.0067(2) 0.5110(3) 0.22176(10) 0.0288(7) Uani 1 1 d . . . . .
H21A H 1.077309 0.504219 0.225755 0.043 Uiso 1 1 calc GR . . . .
H21B H 0.989818 0.558123 0.191866 0.043 Uiso 1 1 calc GR . . . .
H21C H 0.978146 0.432654 0.217888 0.043 Uiso 1 1 calc GR . . . .
C22 C 0.86408(19) 0.3627(2) 0.42973(9) 0.0216(6) Uani 1 1 d . . . . .
H22 H 0.798992 0.370422 0.412144 0.026 Uiso 1 1 calc R . . . .
C23 C 0.8673(2) 0.4475(3) 0.47466(10) 0.0319(7) Uani 1 1 d . . . . .
H23A H 0.928966 0.438044 0.493838 0.048 Uiso 1 1 calc GR . . . .
H23B H 0.813581 0.430041 0.496376 0.048 Uiso 1 1 calc GR . . . .
H23C H 0.861548 0.528346 0.462432 0.048 Uiso 1 1 calc GR . . . .
C24 C 0.8748(2) 0.2361(3) 0.44827(11) 0.0303(7) Uani 1 1 d . . . . .
H24A H 0.873616 0.182847 0.419370 0.045 Uiso 1 1 calc GR . . . .
H24B H 0.821113 0.217020 0.469804 0.045 Uiso 1 1 calc GR . . . .
H24C H 0.936401 0.227503 0.467507 0.045 Uiso 1 1 calc GR . . . .
C25 C 0.54028(17) 0.4487(2) 0.31042(8) 0.0145(5) Uani 1 1 d . . . . .
C26 C 0.49767(18) 0.3856(2) 0.34903(9) 0.0166(5) Uani 1 1 d . . . . .
C27 C 0.39988(18) 0.3590(2) 0.34207(9) 0.0200(5) Uani 1 1 d . . . . .
H27 H 0.368187 0.316183 0.367214 0.024 Uiso 1 1 calc R . . . .
C28 C 0.34760(18) 0.3941(2) 0.29888(9) 0.0198(5) Uani 1 1 d . . . . .
H28 H 0.281563 0.371844 0.294113 0.024 Uiso 1 1 calc R . . . .
C29 C 0.39091(18) 0.4610(2) 0.26293(9) 0.0184(5) Uani 1 1 d . . . . .
H29 H 0.353430 0.487096 0.234367 0.022 Uiso 1 1 calc R . . . .
C30 C 0.48921(18) 0.4910(2) 0.26781(9) 0.0154(5) Uani 1 1 d . . . . .
C31 C 0.55083(19) 0.3535(2) 0.39859(9) 0.0196(5) Uani 1 1 d . . . . .
H31 H 0.621563 0.367399 0.394500 0.024 Uiso 1 1 calc R . . . .
C32 C 0.5184(2) 0.4325(2) 0.44103(9) 0.0269(6) Uani 1 1 d . . . . .
H32A H 0.532651 0.514475 0.433000 0.040 Uiso 1 1 calc GR . . . .
H32B H 0.553233 0.410648 0.472469 0.040 Uiso 1 1 calc GR . . . .
H32C H 0.448575 0.423211 0.444877 0.040 Uiso 1 1 calc GR . . . .
C33 C 0.5377(2) 0.2245(2) 0.41242(10) 0.0252(6) Uani 1 1 d . . . . .
H33A H 0.469858 0.210190 0.419990 0.038 Uiso 1 1 calc GR . . . .
H33B H 0.579401 0.205575 0.441996 0.038 Uiso 1 1 calc GR . . . .
H33C H 0.555399 0.174945 0.384150 0.038 Uiso 1 1 calc GR . . . .
C34 C 0.53262(19) 0.5700(2) 0.22814(9) 0.0184(5) Uani 1 1 d . . . . .
H34 H 0.602433 0.583404 0.237931 0.022 Uiso 1 1 calc R . . . .
C35 C 0.4821(2) 0.6889(2) 0.22554(10) 0.0250(6) Uani 1 1 d . . . . .
H35A H 0.414208 0.678169 0.214260 0.038 Uiso 1 1 calc GR . . . .
H35B H 0.514559 0.739667 0.201766 0.038 Uiso 1 1 calc GR . . . .
H35C H 0.484990 0.725244 0.258926 0.038 Uiso 1 1 calc GR . . . .
C36 C 0.5273(2) 0.5110(2) 0.17608(9) 0.0236(6) Uani 1 1 d . . . . .
H36A H 0.561439 0.435678 0.177912 0.035 Uiso 1 1 calc GR . . . .
H36B H 0.557694 0.561932 0.151622 0.035 Uiso 1 1 calc GR . . . .
H36C H 0.459293 0.497817 0.165584 0.035 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.30294(7) 0.64039(8) 0.41461(3) 0.0508(2) Uani 1 1 d . . . . .
Cl2 Cl 0.28128(6) 0.74752(8) 0.31556(3) 0.0413(2) Uani 1 1 d . . . . .
C37 C 0.2350(2) 0.7408(3) 0.37677(13) 0.0468(9) Uani 1 1 d . . . . .
H37A H 0.238163 0.819630 0.392391 0.056 Uiso 1 1 calc R . . . .
H37B H 0.166276 0.716016 0.374440 0.056 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 1.999(3) . ?
Br2 B1 1.970(3) . ?
Br3 B2 2.017(3) . ?
Br4 B2 2.022(3) . ?
Br5 B2 2.018(3) . ?
Br6 B2 2.022(3) . ?
N1 B1 1.602(3) . ?
N1 C1 1.290(3) . ?
N1 C13 1.466(3) . ?
N2 B1 1.603(3) . ?
N2 C2 1.291(3) . ?
N2 C25 1.464(3) . ?
C1 C2 1.485(3) . ?
C1 C5 1.444(3) . ?
C2 C3 1.442(3) . ?
C3 C4 1.424(3) . ?
C3 C6 1.378(3) . ?
C4 C5 1.427(4) . ?
C4 C9 1.394(3) . ?
C5 C12 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.411(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.415(4) . ?
C9 C10 1.428(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.406(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 C18 1.415(3) . ?
C14 C15 1.397(3) . ?
C14 C19 1.528(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(4) . ?
C18 C22 1.520(3) . ?
C19 H19 1.0000 . ?
C19 C20 1.528(4) . ?
C19 C21 1.534(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
C22 C23 1.537(4) . ?
C22 C24 1.530(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.404(3) . ?
C25 C30 1.396(3) . ?
C26 C27 1.389(3) . ?
C26 C31 1.527(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.379(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.401(3) . ?
C30 C34 1.530(3) . ?
C31 H31 1.0000 . ?
C31 C32 1.527(3) . ?
C31 C33 1.529(4) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34 1.0000 . ?
C34 C35 1.524(4) . ?
C34 C36 1.540(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Cl1 C37 1.769(4) . ?
Cl2 C37 1.777(4) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 B1 109.5(2) . . ?
C1 N1 C13 120.7(2) . . ?
C13 N1 B1 129.7(2) . . ?
C2 N2 B1 109.3(2) . . ?
C2 N2 C25 120.4(2) . . ?
C25 N2 B1 130.18(19) . . ?
Br2 B1 Br1 108.84(13) . . ?
N1 B1 Br1 110.53(17) . . ?
N1 B1 Br2 114.35(17) . . ?
N1 B1 N2 97.93(18) . . ?
N2 B1 Br1 109.79(16) . . ?
N2 B1 Br2 115.01(17) . . ?
Br3 B2 Br4 109.35(14) . . ?
Br3 B2 Br5 109.69(13) . . ?
Br3 B2 Br6 109.62(14) . . ?
Br4 B2 Br6 109.42(13) . . ?
Br5 B2 Br4 108.68(14) . . ?
Br5 B2 Br6 110.06(14) . . ?
N1 C1 C2 111.1(2) . . ?
N1 C1 C5 140.8(2) . . ?
C5 C1 C2 108.1(2) . . ?
N2 C2 C1 111.3(2) . . ?
N2 C2 C3 139.9(2) . . ?
C3 C2 C1 108.7(2) . . ?
C4 C3 C2 104.3(2) . . ?
C6 C3 C2 135.5(2) . . ?
C6 C3 C4 120.1(2) . . ?
C3 C4 C5 114.4(2) . . ?
C9 C4 C3 122.4(2) . . ?
C9 C4 C5 123.2(2) . . ?
C4 C5 C1 104.5(2) . . ?
C12 C5 C1 136.2(2) . . ?
C12 C5 C4 119.3(2) . . ?
C3 C6 H6 121.1 . . ?
C3 C6 C7 117.7(2) . . ?
C7 C6 H6 121.1 . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 116.4(2) . . ?
C4 C9 C10 115.8(2) . . ?
C8 C9 C10 127.8(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 118.5 . . ?
C10 C11 C12 122.9(2) . . ?
C12 C11 H11 118.5 . . ?
C5 C12 C11 117.8(3) . . ?
C5 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C14 C13 N1 119.4(2) . . ?
C14 C13 C18 123.9(2) . . ?
C18 C13 N1 116.6(2) . . ?
C13 C14 C15 116.8(2) . . ?
C13 C14 C19 124.0(2) . . ?
C15 C14 C19 119.1(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.3(2) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C22 123.8(2) . . ?
C17 C18 C13 116.1(2) . . ?
C17 C18 C22 120.0(2) . . ?
C14 C19 H19 108.1 . . ?
C14 C19 C20 110.9(2) . . ?
C14 C19 C21 111.4(2) . . ?
C20 C19 H19 108.1 . . ?
C20 C19 C21 110.2(2) . . ?
C21 C19 H19 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22 107.8 . . ?
C18 C22 C23 110.5(2) . . ?
C18 C22 C24 112.6(2) . . ?
C23 C22 H22 107.8 . . ?
C24 C22 H22 107.8 . . ?
C24 C22 C23 110.0(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N2 116.6(2) . . ?
C30 C25 N2 119.3(2) . . ?
C30 C25 C26 124.0(2) . . ?
C25 C26 C31 123.6(2) . . ?
C27 C26 C25 116.7(2) . . ?
C27 C26 C31 119.5(2) . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 121.1(2) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.5(2) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.4 . . ?
C28 C29 C30 121.2(2) . . ?
C30 C29 H29 119.4 . . ?
C25 C30 C29 116.5(2) . . ?
C25 C30 C34 124.4(2) . . ?
C29 C30 C34 119.1(2) . . ?
C26 C31 H31 107.7 . . ?
C26 C31 C33 112.4(2) . . ?
C32 C31 C26 110.7(2) . . ?
C32 C31 H31 107.7 . . ?
C32 C31 C33 110.4(2) . . ?
C33 C31 H31 107.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34 108.1 . . ?
C30 C34 C36 111.0(2) . . ?
C35 C34 C30 111.3(2) . . ?
C35 C34 H34 108.1 . . ?
C35 C34 C36 110.1(2) . . ?
C36 C34 H34 108.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl1 C37 Cl2 110.35(19) . . ?
Cl1 C37 H37A 109.6 . . ?
Cl1 C37 H37B 109.6 . . ?
Cl2 C37 H37A 109.6 . . ?
Cl2 C37 H37B 109.6 . . ?
H37A C37 H37B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.2(3) . . . . ?
N1 C1 C2 C3 177.4(2) . . . . ?
N1 C1 C5 C4 -177.3(3) . . . . ?
N1 C1 C5 C12 2.0(5) . . . . ?
N1 C13 C14 C15 178.3(2) . . . . ?
N1 C13 C14 C19 -0.3(3) . . . . ?
N1 C13 C18 C17 -179.1(2) . . . . ?
N1 C13 C18 C22 -3.4(3) . . . . ?
N2 C2 C3 C4 177.2(3) . . . . ?
N2 C2 C3 C6 -2.1(5) . . . . ?
N2 C25 C26 C27 179.9(2) . . . . ?
N2 C25 C26 C31 4.5(3) . . . . ?
N2 C25 C30 C29 179.9(2) . . . . ?
N2 C25 C30 C34 -2.4(3) . . . . ?
B1 N1 C1 C2 5.9(3) . . . . ?
B1 N1 C1 C5 -177.4(3) . . . . ?
B1 N1 C13 C14 95.9(3) . . . . ?
B1 N1 C13 C18 -88.3(3) . . . . ?
B1 N2 C2 C1 -6.1(3) . . . . ?
B1 N2 C2 C3 177.9(3) . . . . ?
B1 N2 C25 C26 87.0(3) . . . . ?
B1 N2 C25 C30 -96.7(3) . . . . ?
C1 N1 B1 Br1 106.2(2) . . . . ?
C1 N1 B1 Br2 -130.60(19) . . . . ?
C1 N1 B1 N2 -8.5(2) . . . . ?
C1 N1 C13 C14 -87.4(3) . . . . ?
C1 N1 C13 C18 88.4(3) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C6 -178.1(3) . . . . ?
C1 C5 C12 C11 178.8(3) . . . . ?
C2 N2 B1 Br1 -106.68(19) . . . . ?
C2 N2 B1 Br2 130.18(18) . . . . ?
C2 N2 B1 N1 8.6(2) . . . . ?
C2 N2 C25 C26 -90.2(3) . . . . ?
C2 N2 C25 C30 86.2(3) . . . . ?
C2 C1 C5 C4 -0.5(2) . . . . ?
C2 C1 C5 C12 178.8(3) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C2 C3 C4 C9 178.7(2) . . . . ?
C2 C3 C6 C7 -179.7(3) . . . . ?
C3 C4 C5 C1 1.3(3) . . . . ?
C3 C4 C5 C12 -178.1(2) . . . . ?
C3 C4 C9 C8 1.5(3) . . . . ?
C3 C4 C9 C10 179.5(2) . . . . ?
C3 C6 C7 C8 -0.1(4) . . . . ?
C4 C3 C6 C7 1.1(3) . . . . ?
C4 C5 C12 C11 -2.0(3) . . . . ?
C4 C9 C10 C11 -0.7(3) . . . . ?
C5 C1 C2 N2 -177.7(2) . . . . ?
C5 C1 C2 C3 -0.4(3) . . . . ?
C5 C4 C9 C8 -178.3(2) . . . . ?
C5 C4 C9 C10 -0.3(3) . . . . ?
C6 C3 C4 C5 177.9(2) . . . . ?
C6 C3 C4 C9 -1.9(3) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C4 -0.4(4) . . . . ?
C7 C8 C9 C10 -178.2(2) . . . . ?
C8 C9 C10 C11 177.0(2) . . . . ?
C9 C4 C5 C1 -178.9(2) . . . . ?
C9 C4 C5 C12 1.7(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C5 1.0(4) . . . . ?
C13 N1 B1 Br1 -76.8(3) . . . . ?
C13 N1 B1 Br2 46.4(3) . . . . ?
C13 N1 B1 N2 168.5(2) . . . . ?
C13 N1 C1 C2 -171.46(19) . . . . ?
C13 N1 C1 C5 5.3(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C13 C14 C19 C20 115.3(3) . . . . ?
C13 C14 C19 C21 -121.6(3) . . . . ?
C13 C18 C22 C23 -102.5(3) . . . . ?
C13 C18 C22 C24 134.0(3) . . . . ?
C14 C13 C18 C17 -3.6(4) . . . . ?
C14 C13 C18 C22 172.1(2) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
C15 C14 C19 C20 -63.2(3) . . . . ?
C15 C14 C19 C21 59.9(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C13 1.9(4) . . . . ?
C16 C17 C18 C22 -173.9(2) . . . . ?
C17 C18 C22 C23 73.0(3) . . . . ?
C17 C18 C22 C24 -50.5(3) . . . . ?
C18 C13 C14 C15 2.8(4) . . . . ?
C18 C13 C14 C19 -175.7(2) . . . . ?
C19 C14 C15 C16 178.2(2) . . . . ?
C25 N2 B1 Br1 75.9(3) . . . . ?
C25 N2 B1 Br2 -47.2(3) . . . . ?
C25 N2 B1 N1 -168.8(2) . . . . ?
C25 N2 C2 C1 171.57(19) . . . . ?
C25 N2 C2 C3 -4.4(4) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
C25 C26 C31 C32 104.0(3) . . . . ?
C25 C26 C31 C33 -132.1(3) . . . . ?
C25 C30 C34 C35 -117.3(3) . . . . ?
C25 C30 C34 C36 119.7(3) . . . . ?
C26 C25 C30 C29 -4.0(3) . . . . ?
C26 C25 C30 C34 173.7(2) . . . . ?
C26 C27 C28 C29 -3.0(4) . . . . ?
C27 C26 C31 C32 -71.4(3) . . . . ?
C27 C26 C31 C33 52.5(3) . . . . ?
C27 C28 C29 C30 2.8(4) . . . . ?
C28 C29 C30 C25 0.6(3) . . . . ?
C28 C29 C30 C34 -177.2(2) . . . . ?
C29 C30 C34 C35 60.3(3) . . . . ?
C29 C30 C34 C36 -62.7(3) . . . . ?
C30 C25 C26 C27 3.8(4) . . . . ?
C30 C25 C26 C31 -171.7(2) . . . . ?
C31 C26 C27 C28 175.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound7
_database_code_depnum_ccdc_archive 'CCDC 1946584'
loop_
_audit_author_name
_audit_author_address
'Hans Georg Stammler'
;University of Bielefeld
Germany
;
_audit_update_record             
;
2019-08-12 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;





_audit_creation_date             2019-07-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
  
;
_chemical_formula_moiety         'C36 H40 B Br N2'
_chemical_formula_sum            'C36 H40 B Br N2'
_chemical_formula_weight         591.42
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   12.9150(2)
_cell_length_b                   19.5005(2)
_cell_length_c                   13.4350(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.4998(7)
_cell_angle_gamma                90
_cell_volume                     3169.32(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    40824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.910
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  0.9015
_exptl_absorpt_correction_T_min  0.7332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
  
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_number            62160
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.022
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7123
_reflns_number_total             9239
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect, Bruker AXS, 2004'
_computing_data_reduction        
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         9239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+1.0673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22), C31(H31), C34(H34)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C27(H27), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br 0.74024(2) 0.02417(2) 0.44056(2) 0.02778(6) Uani 1 1 d . . . . .
N1 N 0.74053(11) 0.16710(6) 0.36023(10) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.68617(11) 0.16133(6) 0.50722(10) 0.0165(2) Uani 1 1 d . . . . .
B1 B 0.71997(14) 0.12151(9) 0.43471(14) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.72113(12) 0.23291(7) 0.39048(12) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.68995(13) 0.22979(7) 0.47748(12) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.67692(13) 0.29906(8) 0.51290(12) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.70260(13) 0.34247(8) 0.43892(12) 0.0193(3) Uani 1 1 d . . . . .
C5 C 0.73095(13) 0.30405(8) 0.36149(12) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.76047(15) 0.33903(9) 0.28663(14) 0.0261(4) Uani 1 1 d . . . . .
H6 H 0.779736 0.315211 0.233926 0.031 Uiso 1 1 calc R . . . .
C7 C 0.76131(17) 0.41186(9) 0.29043(15) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.782260 0.436295 0.239285 0.037 Uiso 1 1 calc R . . . .
C8 C 0.73335(16) 0.44860(9) 0.36435(15) 0.0295(4) Uani 1 1 d . . . . .
H8 H 0.734581 0.497297 0.363264 0.035 Uiso 1 1 calc R . . . .
C9 C 0.70238(14) 0.41348(8) 0.44301(14) 0.0234(3) Uani 1 1 d . . . . .
C10 C 0.67356(16) 0.44326(9) 0.52664(16) 0.0295(4) Uani 1 1 d . . . . .
H10 H 0.670950 0.491723 0.532533 0.035 Uiso 1 1 calc R . . . .
C11 C 0.64949(16) 0.40209(9) 0.59892(15) 0.0305(4) Uani 1 1 d . . . . .
H11 H 0.631187 0.423131 0.654371 0.037 Uiso 1 1 calc R . . . .
C12 C 0.65099(14) 0.32910(8) 0.59374(14) 0.0246(3) Uani 1 1 d . . . . .
H12 H 0.634469 0.301886 0.644901 0.029 Uiso 1 1 calc R . . . .
C13 C 0.76475(13) 0.15507(8) 0.26512(12) 0.0188(3) Uani 1 1 d . . . . .
C14 C 0.87518(14) 0.15758(8) 0.27039(14) 0.0231(3) Uani 1 1 d . . . . .
C15 C 0.89490(16) 0.14825(9) 0.17543(15) 0.0300(4) Uani 1 1 d . . . . .
H15 H 0.968823 0.148861 0.176457 0.036 Uiso 1 1 calc R . . . .
C16 C 0.80934(18) 0.13816(9) 0.08009(15) 0.0321(4) Uani 1 1 d . . . . .
H16 H 0.824909 0.132795 0.016465 0.039 Uiso 1 1 calc R . . . .
C17 C 0.70096(16) 0.13584(9) 0.07677(14) 0.0285(4) Uani 1 1 d . . . . .
H17 H 0.642813 0.128604 0.010839 0.034 Uiso 1 1 calc R . . . .
C18 C 0.67617(14) 0.14406(8) 0.16981(13) 0.0230(3) Uani 1 1 d . . . . .
C19 C 0.96922(14) 0.17027(9) 0.37417(15) 0.0281(4) Uani 1 1 d . . . . .
H19 H 0.936357 0.186872 0.427007 0.034 Uiso 1 1 calc R . . . .
C20 C 1.0325(2) 0.10384(12) 0.4178(2) 0.0518(6) Uani 1 1 d . . . . .
H20A H 0.980615 0.068748 0.423740 0.078 Uiso 1 1 calc GR . . . .
H20B H 1.087976 0.112584 0.488087 0.078 Uiso 1 1 calc GR . . . .
H20C H 1.069184 0.087763 0.369490 0.078 Uiso 1 1 calc GR . . . .
C21 C 1.04864(17) 0.22574(11) 0.36336(19) 0.0413(5) Uani 1 1 d . . . . .
H21A H 1.086207 0.209448 0.315859 0.062 Uiso 1 1 calc GR . . . .
H21B H 1.103585 0.235770 0.433443 0.062 Uiso 1 1 calc GR . . . .
H21C H 1.006930 0.267486 0.333856 0.062 Uiso 1 1 calc GR . . . .
C22 C 0.55716(15) 0.14201(10) 0.16510(14) 0.0286(4) Uani 1 1 d . . . . .
H22 H 0.557509 0.148876 0.238980 0.034 Uiso 1 1 calc R . . . .
C23 C 0.50354(19) 0.07283(12) 0.1262(2) 0.0472(5) Uani 1 1 d . . . . .
H23A H 0.498208 0.065824 0.052314 0.071 Uiso 1 1 calc GR . . . .
H23B H 0.429350 0.071852 0.130464 0.071 Uiso 1 1 calc GR . . . .
H23C H 0.548566 0.036280 0.170726 0.071 Uiso 1 1 calc GR . . . .
C24 C 0.48954(18) 0.20057(11) 0.09620(19) 0.0436(5) Uani 1 1 d . . . . .
H24A H 0.526759 0.244355 0.121351 0.065 Uiso 1 1 calc GR . . . .
H24B H 0.415645 0.201431 0.101188 0.065 Uiso 1 1 calc GR . . . .
H24C H 0.483060 0.193311 0.022073 0.065 Uiso 1 1 calc GR . . . .
C25 C 0.65416(14) 0.13918(8) 0.59434(12) 0.0198(3) Uani 1 1 d . . . . .
C26 C 0.73647(16) 0.12461(9) 0.69175(13) 0.0273(4) Uani 1 1 d . . . . .
C27 C 0.7022(2) 0.10015(10) 0.77319(15) 0.0419(5) Uani 1 1 d . . . . .
H27 H 0.756098 0.089142 0.840230 0.050 Uiso 1 1 calc R . . . .
C28 C 0.5915(2) 0.09174(11) 0.75777(17) 0.0466(6) Uani 1 1 d . . . . .
H28 H 0.570059 0.074807 0.814013 0.056 Uiso 1 1 calc R . . . .
C29 C 0.51198(19) 0.10769(10) 0.66164(17) 0.0388(5) Uani 1 1 d . . . . .
H29 H 0.436121 0.102190 0.652571 0.047 Uiso 1 1 calc R . . . .
C30 C 0.54097(15) 0.13182(8) 0.57716(14) 0.0259(4) Uani 1 1 d . . . . .
C31 C 0.85807(17) 0.13535(10) 0.71067(15) 0.0359(4) Uani 1 1 d . . . . .
H31 H 0.865181 0.148766 0.641518 0.043 Uiso 1 1 calc R . . . .
C32 C 0.90504(19) 0.19412(11) 0.79013(17) 0.0435(5) Uani 1 1 d . . . . .
H32A H 0.859911 0.235347 0.765490 0.065 Uiso 1 1 calc GR . . . .
H32B H 0.981312 0.203622 0.795438 0.065 Uiso 1 1 calc GR . . . .
H32C H 0.903827 0.180838 0.860059 0.065 Uiso 1 1 calc GR . . . .
C33 C 0.9249(2) 0.06946(13) 0.7490(2) 0.0592(7) Uani 1 1 d . . . . .
H33A H 0.928696 0.059082 0.821585 0.089 Uiso 1 1 calc GR . . . .
H33B H 0.999875 0.075761 0.748105 0.089 Uiso 1 1 calc GR . . . .
H33C H 0.888977 0.031434 0.701915 0.089 Uiso 1 1 calc GR . . . .
C34 C 0.45383(15) 0.14753(10) 0.46959(17) 0.0330(4) Uani 1 1 d . . . . .
H34 H 0.485356 0.182913 0.434412 0.040 Uiso 1 1 calc R . . . .
C35 C 0.42788(17) 0.08376(11) 0.39822(17) 0.0384(5) Uani 1 1 d . . . . .
H35A H 0.495868 0.067108 0.389654 0.058 Uiso 1 1 calc GR . . . .
H35B H 0.373820 0.095584 0.328477 0.058 Uiso 1 1 calc GR . . . .
H35C H 0.397373 0.047831 0.430931 0.058 Uiso 1 1 calc GR . . . .
C36 C 0.34696(18) 0.17688(13) 0.4773(3) 0.0571(7) Uani 1 1 d . . . . .
H36A H 0.309757 0.141558 0.504388 0.086 Uiso 1 1 calc GR . . . .
H36B H 0.298195 0.191615 0.406680 0.086 Uiso 1 1 calc GR . . . .
H36C H 0.364492 0.216244 0.525680 0.086 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 B1 1.9139(18) . ?
N1 B1 1.431(2) . ?
N1 C1 1.3951(19) . ?
N1 C13 1.4372(19) . ?
N2 B1 1.428(2) . ?
N2 C2 1.3992(19) . ?
N2 C25 1.4374(19) . ?
C1 C2 1.364(2) . ?
C1 C5 1.458(2) . ?
C2 C3 1.461(2) . ?
C3 C4 1.430(2) . ?
C3 C12 1.375(2) . ?
C4 C5 1.430(2) . ?
C4 C9 1.386(2) . ?
C5 C6 1.375(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.421(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.429(2) . ?
C9 C10 1.425(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.425(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(2) . ?
C13 C18 1.403(2) . ?
C14 C15 1.398(2) . ?
C14 C19 1.515(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(2) . ?
C18 C22 1.517(2) . ?
C19 H19 1.0000 . ?
C19 C20 1.534(3) . ?
C19 C21 1.532(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
C22 C23 1.523(3) . ?
C22 C24 1.535(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.396(2) . ?
C25 C30 1.405(2) . ?
C26 C27 1.400(3) . ?
C26 C31 1.515(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.382(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.375(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.396(2) . ?
C30 C34 1.520(3) . ?
C31 H31 1.0000 . ?
C31 C32 1.539(3) . ?
C31 C33 1.533(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34 1.0000 . ?
C34 C35 1.534(3) . ?
C34 C36 1.531(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 N1 C13 132.19(13) . . ?
C1 N1 B1 105.75(12) . . ?
C1 N1 C13 121.77(12) . . ?
B1 N2 C25 129.47(13) . . ?
C2 N2 B1 105.93(12) . . ?
C2 N2 C25 124.61(12) . . ?
N1 B1 Br1 126.06(12) . . ?
N2 B1 Br1 125.54(12) . . ?
N2 B1 N1 108.35(13) . . ?
N1 C1 C5 139.10(14) . . ?
C2 C1 N1 110.21(13) . . ?
C2 C1 C5 110.53(13) . . ?
N2 C2 C3 140.30(14) . . ?
C1 C2 N2 109.73(13) . . ?
C1 C2 C3 109.87(13) . . ?
C4 C3 C2 103.86(13) . . ?
C12 C3 C2 137.64(15) . . ?
C12 C3 C4 118.48(14) . . ?
C5 C4 C3 112.11(13) . . ?
C9 C4 C3 124.02(15) . . ?
C9 C4 C5 123.85(15) . . ?
C4 C5 C1 103.63(13) . . ?
C6 C5 C1 137.69(15) . . ?
C6 C5 C4 118.66(14) . . ?
C5 C6 H6 121.0 . . ?
C5 C6 C7 118.04(16) . . ?
C7 C6 H6 121.0 . . ?
C6 C7 H7 118.4 . . ?
C8 C7 C6 123.19(17) . . ?
C8 C7 H7 118.4 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.88(16) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 116.39(16) . . ?
C4 C9 C10 116.31(15) . . ?
C10 C9 C8 127.29(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.29(15) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 118.7 . . ?
C10 C11 C12 122.50(16) . . ?
C12 C11 H11 118.7 . . ?
C3 C12 C11 118.39(16) . . ?
C3 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 N1 118.88(14) . . ?
C18 C13 N1 118.33(14) . . ?
C18 C13 C14 122.73(15) . . ?
C13 C14 C19 121.68(15) . . ?
C15 C14 C13 117.14(16) . . ?
C15 C14 C19 121.18(16) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.50(17) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.37(16) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.69(17) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 117.56(16) . . ?
C13 C18 C22 122.19(14) . . ?
C17 C18 C22 120.24(15) . . ?
C14 C19 H19 107.7 . . ?
C14 C19 C20 111.21(16) . . ?
C14 C19 C21 112.07(16) . . ?
C20 C19 H19 107.7 . . ?
C21 C19 H19 107.7 . . ?
C21 C19 C20 110.36(17) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22 107.6 . . ?
C18 C22 C23 111.71(16) . . ?
C18 C22 C24 111.08(16) . . ?
C23 C22 H22 107.6 . . ?
C23 C22 C24 110.96(17) . . ?
C24 C22 H22 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N2 118.87(15) . . ?
C26 C25 C30 122.68(15) . . ?
C30 C25 N2 118.44(14) . . ?
C25 C26 C27 117.19(18) . . ?
C25 C26 C31 122.23(16) . . ?
C27 C26 C31 120.57(17) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.15(19) . . ?
C28 C27 H27 119.4 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.48(18) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.0(2) . . ?
C30 C29 H29 119.5 . . ?
C25 C30 C34 121.13(15) . . ?
C29 C30 C25 117.44(18) . . ?
C29 C30 C34 121.41(17) . . ?
C26 C31 H31 107.9 . . ?
C26 C31 C32 110.68(18) . . ?
C26 C31 C33 111.68(18) . . ?
C32 C31 H31 107.9 . . ?
C33 C31 H31 107.9 . . ?
C33 C31 C32 110.62(17) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34 107.5 . . ?
C30 C34 C35 110.97(16) . . ?
C30 C34 C36 113.34(19) . . ?
C35 C34 H34 107.5 . . ?
C36 C34 H34 107.5 . . ?
C36 C34 C35 109.91(17) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -0.78(18) . . . . ?
N1 C1 C2 C3 176.25(13) . . . . ?
N1 C1 C5 C4 -174.89(18) . . . . ?
N1 C1 C5 C6 3.3(4) . . . . ?
N1 C13 C14 C15 -177.57(14) . . . . ?
N1 C13 C14 C19 2.1(2) . . . . ?
N1 C13 C18 C17 176.85(14) . . . . ?
N1 C13 C18 C22 -2.2(2) . . . . ?
N2 C2 C3 C4 175.90(19) . . . . ?
N2 C2 C3 C12 -2.3(4) . . . . ?
N2 C25 C26 C27 -177.11(15) . . . . ?
N2 C25 C26 C31 3.7(2) . . . . ?
N2 C25 C30 C29 177.54(14) . . . . ?
N2 C25 C30 C34 -0.6(2) . . . . ?
B1 N1 C1 C2 -0.28(17) . . . . ?
B1 N1 C1 C5 174.52(19) . . . . ?
B1 N1 C13 C14 -98.5(2) . . . . ?
B1 N1 C13 C18 84.1(2) . . . . ?
B1 N2 C2 C1 1.50(17) . . . . ?
B1 N2 C2 C3 -174.13(19) . . . . ?
B1 N2 C25 C26 82.1(2) . . . . ?
B1 N2 C25 C30 -96.6(2) . . . . ?
C1 N1 B1 Br1 -176.32(12) . . . . ?
C1 N1 B1 N2 1.20(17) . . . . ?
C1 N1 C13 C14 88.61(18) . . . . ?
C1 N1 C13 C18 -88.82(18) . . . . ?
C1 C2 C3 C4 0.28(17) . . . . ?
C1 C2 C3 C12 -177.95(19) . . . . ?
C1 C5 C6 C7 -177.95(18) . . . . ?
C2 N2 B1 Br1 175.88(12) . . . . ?
C2 N2 B1 N1 -1.65(17) . . . . ?
C2 N2 C25 C26 -97.70(18) . . . . ?
C2 N2 C25 C30 83.52(19) . . . . ?
C2 C1 C5 C4 -0.11(17) . . . . ?
C2 C1 C5 C6 178.10(19) . . . . ?
C2 C3 C4 C5 -0.36(18) . . . . ?
C2 C3 C4 C9 -179.07(15) . . . . ?
C2 C3 C12 C11 178.90(18) . . . . ?
C3 C4 C5 C1 0.29(18) . . . . ?
C3 C4 C5 C6 -178.33(15) . . . . ?
C3 C4 C9 C8 178.19(16) . . . . ?
C3 C4 C9 C10 -0.5(2) . . . . ?
C4 C3 C12 C11 0.9(2) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C4 C9 C10 C11 1.0(3) . . . . ?
C5 C1 C2 N2 -177.14(13) . . . . ?
C5 C1 C2 C3 -0.11(18) . . . . ?
C5 C4 C9 C8 -0.4(2) . . . . ?
C5 C4 C9 C10 -179.07(16) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
C7 C8 C9 C10 178.44(19) . . . . ?
C8 C9 C10 C11 -177.54(18) . . . . ?
C9 C4 C5 C1 179.01(15) . . . . ?
C9 C4 C5 C6 0.4(2) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C3 -0.4(3) . . . . ?
C12 C3 C4 C5 178.29(14) . . . . ?
C12 C3 C4 C9 -0.4(2) . . . . ?
C13 N1 B1 Br1 10.0(3) . . . . ?
C13 N1 B1 N2 -172.52(15) . . . . ?
C13 N1 C1 C2 174.25(14) . . . . ?
C13 N1 C1 C5 -11.0(3) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C13 C14 C19 C20 104.3(2) . . . . ?
C13 C14 C19 C21 -131.69(17) . . . . ?
C13 C18 C22 C23 -118.83(19) . . . . ?
C13 C18 C22 C24 116.69(18) . . . . ?
C14 C13 C18 C17 -0.5(2) . . . . ?
C14 C13 C18 C22 -179.52(15) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C15 C14 C19 C20 -76.1(2) . . . . ?
C15 C14 C19 C21 47.9(2) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C13 0.4(2) . . . . ?
C16 C17 C18 C22 179.49(16) . . . . ?
C17 C18 C22 C23 62.1(2) . . . . ?
C17 C18 C22 C24 -62.3(2) . . . . ?
C18 C13 C14 C15 -0.3(2) . . . . ?
C18 C13 C14 C19 179.36(15) . . . . ?
C19 C14 C15 C16 -178.54(16) . . . . ?
C25 N2 B1 Br1 -4.0(2) . . . . ?
C25 N2 B1 N1 178.49(14) . . . . ?
C25 N2 C2 C1 -178.63(14) . . . . ?
C25 N2 C2 C3 5.7(3) . . . . ?
C25 C26 C27 C28 -0.8(3) . . . . ?
C25 C26 C31 C32 111.97(19) . . . . ?
C25 C26 C31 C33 -124.3(2) . . . . ?
C25 C30 C34 C35 89.1(2) . . . . ?
C25 C30 C34 C36 -146.67(17) . . . . ?
C26 C25 C30 C29 -1.2(2) . . . . ?
C26 C25 C30 C34 -179.38(16) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C27 C26 C31 C32 -67.2(2) . . . . ?
C27 C26 C31 C33 56.5(2) . . . . ?
C27 C28 C29 C30 0.8(3) . . . . ?
C28 C29 C30 C25 -0.1(3) . . . . ?
C28 C29 C30 C34 178.12(18) . . . . ?
C29 C30 C34 C35 -89.0(2) . . . . ?
C29 C30 C34 C36 35.2(2) . . . . ?
C30 C25 C26 C27 1.6(2) . . . . ?
C30 C25 C26 C31 -177.57(16) . . . . ?
C31 C26 C27 C28 178.39(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
