# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1478588'
_audit_update_record             
;
2016-05-07 deposited with the CCDC.
2016-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br N2 O2'
_chemical_formula_weight         396.26

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'
O O 0.0106 0.0060 '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'

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

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

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

_cell_length_a                   21.0000(18)
_cell_length_b                   7.6152(6)
_cell_length_c                   23.7899(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.403(2)
_cell_angle_gamma                90
_cell_volume                     3517.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    179(2)
_cell_measurement_reflns_used    6919
_cell_measurement_theta_min      2.568
_cell_measurement_theta_max      26.024

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.353
_shelx_estimated_absorpt_T_min   0.677
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      179(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34501
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.568
_diffrn_reflns_theta_max         26.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6919
_reflns_number_gt                4689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+3.5264P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6919
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.77602(17) 0.1779(5) 0.30442(14) 0.0196(8) Uani 1 1 d . . . . .
C2 C 0.84524(17) 0.1580(5) 0.33719(15) 0.0258(9) Uani 1 1 d . . . . .
H2 H 0.8785 0.1304 0.3216 0.031 Uiso 1 1 calc R U . . .
C3 C 0.85693(18) 0.1875(5) 0.39954(15) 0.0262(9) Uani 1 1 d . . . . .
C4 C 0.79233(18) 0.2251(5) 0.40260(15) 0.0234(8) Uani 1 1 d . . . . .
C5 C 0.7842(2) 0.2548(5) 0.45687(15) 0.0319(9) Uani 1 1 d . . . . .
H5 H 0.7411 0.2764 0.4580 0.038 Uiso 1 1 calc R U . . .
C6 C 0.8429(2) 0.2507(6) 0.50913(16) 0.0423(11) Uani 1 1 d . . . . .
H6 H 0.8394 0.2703 0.5464 0.051 Uiso 1 1 calc R U . . .
C7 C 0.9078(2) 0.2179(6) 0.50734(17) 0.0435(12) Uani 1 1 d . . . . .
H7 H 0.9465 0.2180 0.5434 0.052 Uiso 1 1 calc R U . . .
C8 C 0.9152(2) 0.1855(6) 0.45358(17) 0.0379(11) Uani 1 1 d . . . . .
H8 H 0.9585 0.1626 0.4530 0.045 Uiso 1 1 calc R U . . .
C9 C 0.73332(17) 0.1654(5) 0.24138(14) 0.0213(8) Uani 1 1 d . . . . .
H9 H 0.7505 0.1188 0.2139 0.026 Uiso 1 1 calc R U . . .
C10 C 0.66805(17) 0.2219(5) 0.22241(14) 0.0217(8) Uani 1 1 d . . . . .
C11 C 0.61999(19) 0.2238(5) 0.15811(15) 0.0237(8) Uani 1 1 d . . . . .
C12 C 0.6092(2) 0.1950(6) 0.05539(15) 0.0428(11) Uani 1 1 d . . . . .
H12A H 0.5735 0.2835 0.0464 0.051 Uiso 1 1 calc R U . . .
H12B H 0.5874 0.0813 0.0433 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6549(2) 0.2338(6) 0.02185(17) 0.0486(12) Uani 1 1 d . . . . .
H13A H 0.6281 0.2345 -0.0211 0.073 Uiso 1 1 calc R U . . .
H13B H 0.6761 0.3466 0.0341 0.073 Uiso 1 1 calc R U . . .
H13C H 0.6899 0.1452 0.0310 0.073 Uiso 1 1 calc R U . . .
C14 C 0.66966(16) 0.2252(4) 0.32501(14) 0.0184(8) Uani 1 1 d . . . . .
H14 H 0.6579 0.3072 0.3513 0.022 Uiso 1 1 calc R U . . .
C15 C 0.64034(17) 0.0463(5) 0.33027(14) 0.0196(8) Uani 1 1 d . . . . .
C16 C 0.6772(2) -0.1067(5) 0.33447(16) 0.0307(9) Uani 1 1 d . . . . .
H16 H 0.7220 -0.1002 0.3359 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6488(2) -0.2695(6) 0.3365(2) 0.0459(12) Uani 1 1 d . . . . .
H17 H 0.6747 -0.3708 0.3397 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5821(2) -0.2818(6) 0.33385(19) 0.0457(12) Uani 1 1 d . . . . .
H18 H 0.5628 -0.3913 0.3345 0.055 Uiso 1 1 calc R U . . .
C19 C 0.5440(2) -0.1315(6) 0.33014(16) 0.0340(10) Uani 1 1 d . . . . .
H19 H 0.4991 -0.1386 0.3285 0.041 Uiso 1 1 calc R U . . .
C20 C 0.57365(18) 0.0299(5) 0.32886(14) 0.0230(8) Uani 1 1 d . . . . .
C21 C 0.22570(18) -0.3749(5) 0.19660(15) 0.0238(8) Uani 1 1 d . . . . .
C22 C 0.15647(18) -0.3534(5) 0.16559(15) 0.0285(9) Uani 1 1 d . . . . .
H22 H 0.1241 -0.3289 0.1825 0.034 Uiso 1 1 calc R U . . .
C23 C 0.14292(18) -0.3752(5) 0.10253(16) 0.0269(9) Uani 1 1 d . . . . .
C24 C 0.20633(18) -0.4114(5) 0.09734(15) 0.0242(8) Uani 1 1 d . . . . .
C25 C 0.2126(2) -0.4309(5) 0.04176(16) 0.0336(10) Uani 1 1 d . . . . .
H25 H 0.2551 -0.4515 0.0392 0.040 Uiso 1 1 calc R U . . .
C26 C 0.1532(2) -0.4185(6) -0.00960(17) 0.0399(11) Uani 1 1 d . . . . .
H26 H 0.1555 -0.4316 -0.0476 0.048 Uiso 1 1 calc R U . . .
C27 C 0.0897(2) -0.3866(6) -0.00577(18) 0.0442(11) Uani 1 1 d . . . . .
H27 H 0.0506 -0.3797 -0.0414 0.053 Uiso 1 1 calc R U . . .
C28 C 0.08323(19) -0.3652(6) 0.04907(17) 0.0376(10) Uani 1 1 d . . . . .
H28 H 0.0404 -0.3447 0.0509 0.045 Uiso 1 1 calc R U . . .
C29 C 0.27026(17) -0.3657(5) 0.25944(15) 0.0242(8) Uani 1 1 d . . . . .
H29 H 0.2543 -0.3216 0.2881 0.029 Uiso 1 1 calc R U . . .
C30 C 0.33514(18) -0.4216(5) 0.27615(15) 0.0239(8) Uani 1 1 d . . . . .
C31 C 0.3855(2) -0.4216(5) 0.33977(16) 0.0282(9) Uani 1 1 d . . . . .
C32 C 0.4016(2) -0.3828(6) 0.44313(16) 0.0464(12) Uani 1 1 d . . . . .
H32A H 0.4251 -0.2706 0.4528 0.056 Uiso 1 1 calc R U . . .
H32B H 0.4359 -0.4751 0.4522 0.056 Uiso 1 1 calc R U . . .
C33 C 0.3578(3) -0.4082(7) 0.47961(18) 0.0572(14) Uani 1 1 d . . . . .
H33A H 0.3864 -0.4051 0.5221 0.086 Uiso 1 1 calc R U . . .
H33B H 0.3242 -0.3161 0.4703 0.086 Uiso 1 1 calc R U . . .
H33C H 0.3349 -0.5197 0.4697 0.086 Uiso 1 1 calc R U . . .
C34 C 0.32999(17) -0.4214(5) 0.17204(15) 0.0212(8) Uani 1 1 d . . . . .
H34 H 0.3402 -0.5030 0.1447 0.025 Uiso 1 1 calc R U . . .
C35 C 0.35985(17) -0.2428(5) 0.16710(14) 0.0192(8) Uani 1 1 d . . . . .
C36 C 0.42497(17) -0.2290(5) 0.16416(14) 0.0223(8) Uani 1 1 d . . . . .
C37 C 0.4554(2) -0.0692(5) 0.16323(16) 0.0294(9) Uani 1 1 d . . . . .
H37 H 0.4987 -0.0640 0.1611 0.035 Uiso 1 1 calc R U . . .
C38 C 0.4211(2) 0.0821(5) 0.16547(17) 0.0373(10) Uani 1 1 d . . . . .
H38 H 0.4416 0.1906 0.1660 0.045 Uiso 1 1 calc R U . . .
C39 C 0.3561(2) 0.0736(5) 0.16698(18) 0.0396(11) Uani 1 1 d . . . . .
H39 H 0.3325 0.1765 0.1677 0.048 Uiso 1 1 calc R U . . .
C40 C 0.3258(2) -0.0880(5) 0.16743(17) 0.0313(10) Uani 1 1 d . . . . .
H40 H 0.2817 -0.0921 0.1680 0.038 Uiso 1 1 calc R U . . .
N1 N 0.74387(13) 0.2243(4) 0.34379(12) 0.0204(7) Uani 1 1 d . . . . .
N2 N 0.64129(14) 0.2948(4) 0.26279(12) 0.0209(7) Uani 1 1 d . . . . .
N3 N 0.25586(14) -0.4171(4) 0.15531(12) 0.0219(7) Uani 1 1 d . . . . .
N4 N 0.36032(15) -0.4921(4) 0.23432(12) 0.0232(7) Uani 1 1 d . . . . .
O1 O 0.55915(12) 0.2515(3) 0.14292(10) 0.0333(7) Uani 1 1 d . . . . .
O2 O 0.65172(12) 0.1950(4) 0.12013(10) 0.0307(6) Uani 1 1 d . . . . .
O3 O 0.44617(13) -0.4499(4) 0.35299(11) 0.0376(7) Uani 1 1 d . . . . .
O4 O 0.35632(13) -0.3886(4) 0.37941(10) 0.0344(7) Uani 1 1 d . . . . .
Br1 Br 0.52165(2) 0.23456(5) 0.32905(2) 0.03449(13) Uani 1 1 d . . . . .
Br2 Br 0.47492(2) -0.43589(5) 0.16135(2) 0.03496(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(4) . ?
C1 N1 1.393(4) . ?
C1 C9 1.427(4) . ?
C2 C3 1.426(5) . ?
C2 H2 0.9300 . ?
C3 C8 1.397(5) . ?
C3 C4 1.415(5) . ?
C4 N1 1.381(4) . ?
C4 C5 1.384(5) . ?
C5 C6 1.378(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.340(5) . ?
C9 H9 0.9300 . ?
C10 N2 1.400(4) . ?
C10 C11 1.477(5) . ?
C11 O1 1.206(4) . ?
C11 O2 1.329(4) . ?
C12 O2 1.456(4) . ?
C12 C13 1.492(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N1 1.448(4) . ?
C14 N2 1.468(4) . ?
C14 C15 1.520(5) . ?
C14 H14 0.9800 . ?
C15 C16 1.381(5) . ?
C15 C20 1.394(5) . ?
C16 C17 1.384(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(5) . ?
C19 H19 0.9300 . ?
C20 Br1 1.904(4) . ?
C21 C22 1.367(5) . ?
C21 N3 1.394(4) . ?
C21 C29 1.432(5) . ?
C22 C23 1.426(5) . ?
C22 H22 0.9300 . ?
C23 C28 1.407(5) . ?
C23 C24 1.411(5) . ?
C24 N3 1.376(4) . ?
C24 C25 1.386(5) . ?
C25 C26 1.377(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.391(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.372(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.335(5) . ?
C29 H29 0.9300 . ?
C30 N4 1.399(4) . ?
C30 C31 1.480(5) . ?
C31 O3 1.210(4) . ?
C31 O4 1.330(4) . ?
C32 O4 1.451(4) . ?
C32 C33 1.497(6) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 N3 1.453(4) . ?
C34 N4 1.473(4) . ?
C34 C35 1.521(5) . ?
C34 H34 0.9800 . ?
C35 C40 1.381(5) . ?
C35 C36 1.400(5) . ?
C36 C37 1.379(5) . ?
C36 Br2 1.908(4) . ?
C37 C38 1.371(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.380(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.387(5) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 109.0(3) . . ?
C2 C1 C9 134.1(3) . . ?
N1 C1 C9 116.9(3) . . ?
C1 C2 C3 107.4(3) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C8 C3 C4 118.4(3) . . ?
C8 C3 C2 134.3(4) . . ?
C4 C3 C2 107.3(3) . . ?
N1 C4 C5 129.8(3) . . ?
N1 C4 C3 107.3(3) . . ?
C5 C4 C3 122.8(3) . . ?
C6 C5 C4 116.9(4) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C3 119.1(4) . . ?
C7 C8 H8 120.5 . . ?
C3 C8 H8 120.5 . . ?
C10 C9 C1 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C1 C9 H9 120.5 . . ?
C9 C10 N2 121.5(3) . . ?
C9 C10 C11 124.0(3) . . ?
N2 C10 C11 114.3(3) . . ?
O1 C11 O2 125.0(3) . . ?
O1 C11 C10 122.7(3) . . ?
O2 C11 C10 112.4(3) . . ?
O2 C12 C13 107.8(3) . . ?
O2 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
O2 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 N2 106.7(3) . . ?
N1 C14 C15 113.1(3) . . ?
N2 C14 C15 112.7(3) . . ?
N1 C14 H14 108.0 . . ?
N2 C14 H14 108.0 . . ?
C15 C14 H14 108.0 . . ?
C16 C15 C20 117.2(3) . . ?
C16 C15 C14 121.9(3) . . ?
C20 C15 C14 120.9(3) . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 118.9(4) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C15 122.4(4) . . ?
C19 C20 Br1 117.6(3) . . ?
C15 C20 Br1 119.9(3) . . ?
C22 C21 N3 108.8(3) . . ?
C22 C21 C29 134.1(3) . . ?
N3 C21 C29 117.1(3) . . ?
C21 C22 C23 107.4(3) . . ?
C21 C22 H22 126.3 . . ?
C23 C22 H22 126.3 . . ?
C28 C23 C24 118.5(3) . . ?
C28 C23 C22 134.1(4) . . ?
C24 C23 C22 107.4(3) . . ?
N3 C24 C25 130.0(3) . . ?
N3 C24 C23 107.3(3) . . ?
C25 C24 C23 122.7(3) . . ?
C26 C25 C24 117.1(4) . . ?
C26 C25 H25 121.4 . . ?
C24 C25 H25 121.4 . . ?
C25 C26 C27 121.4(4) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C28 C27 C26 121.8(4) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C27 C28 C23 118.4(4) . . ?
C27 C28 H28 120.8 . . ?
C23 C28 H28 120.8 . . ?
C30 C29 C21 118.8(3) . . ?
C30 C29 H29 120.6 . . ?
C21 C29 H29 120.6 . . ?
C29 C30 N4 122.0(3) . . ?
C29 C30 C31 123.7(3) . . ?
N4 C30 C31 114.3(3) . . ?
O3 C31 O4 125.0(3) . . ?
O3 C31 C30 122.5(3) . . ?
O4 C31 C30 112.5(3) . . ?
O4 C32 C33 107.4(3) . . ?
O4 C32 H32A 110.2 . . ?
C33 C32 H32A 110.2 . . ?
O4 C32 H32B 110.2 . . ?
C33 C32 H32B 110.2 . . ?
H32A C32 H32B 108.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N3 C34 N4 106.9(3) . . ?
N3 C34 C35 112.9(3) . . ?
N4 C34 C35 111.8(3) . . ?
N3 C34 H34 108.4 . . ?
N4 C34 H34 108.4 . . ?
C35 C34 H34 108.4 . . ?
C40 C35 C36 117.0(3) . . ?
C40 C35 C34 122.2(3) . . ?
C36 C35 C34 120.7(3) . . ?
C37 C36 C35 122.3(3) . . ?
C37 C36 Br2 117.6(3) . . ?
C35 C36 Br2 120.0(3) . . ?
C38 C37 C36 119.2(4) . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?
C37 C38 C39 120.1(4) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C38 C39 C40 120.2(4) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C35 C40 C39 121.2(4) . . ?
C35 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C4 N1 C1 108.9(3) . . ?
C4 N1 C14 127.1(3) . . ?
C1 N1 C14 122.3(3) . . ?
C10 N2 C14 115.7(3) . . ?
C24 N3 C21 109.0(3) . . ?
C24 N3 C34 126.7(3) . . ?
C21 N3 C34 122.6(3) . . ?
C30 N4 C34 116.1(3) . . ?
C11 O2 C12 117.1(3) . . ?
C31 O4 C32 116.8(3) . . ?

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 C3 1.8(4) . . . . ?
C9 C1 C2 C3 -180.0(4) . . . . ?
C1 C2 C3 C8 179.8(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C8 C3 C4 N1 178.3(3) . . . . ?
C2 C3 C4 N1 -2.0(4) . . . . ?
C8 C3 C4 C5 -2.0(6) . . . . ?
C2 C3 C4 C5 177.7(3) . . . . ?
N1 C4 C5 C6 -178.7(4) . . . . ?
C3 C4 C5 C6 1.6(6) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C5 C6 C7 C8 -1.1(7) . . . . ?
C6 C7 C8 C3 0.7(6) . . . . ?
C4 C3 C8 C7 0.7(6) . . . . ?
C2 C3 C8 C7 -178.9(4) . . . . ?
C2 C1 C9 C10 -168.8(4) . . . . ?
N1 C1 C9 C10 9.4(5) . . . . ?
C1 C9 C10 N2 0.9(5) . . . . ?
C1 C9 C10 C11 176.9(3) . . . . ?
C9 C10 C11 O1 169.3(4) . . . . ?
N2 C10 C11 O1 -14.5(5) . . . . ?
C9 C10 C11 O2 -11.9(5) . . . . ?
N2 C10 C11 O2 164.4(3) . . . . ?
N1 C14 C15 C16 -18.3(4) . . . . ?
N2 C14 C15 C16 102.9(4) . . . . ?
N1 C14 C15 C20 164.0(3) . . . . ?
N2 C14 C15 C20 -74.8(4) . . . . ?
C20 C15 C16 C17 0.7(5) . . . . ?
C14 C15 C16 C17 -177.1(3) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C19 -1.1(7) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C18 C19 C20 C15 1.0(5) . . . . ?
C18 C19 C20 Br1 -176.0(3) . . . . ?
C16 C15 C20 C19 -1.5(5) . . . . ?
C14 C15 C20 C19 176.3(3) . . . . ?
C16 C15 C20 Br1 175.5(2) . . . . ?
C14 C15 C20 Br1 -6.7(4) . . . . ?
N3 C21 C22 C23 -2.5(4) . . . . ?
C29 C21 C22 C23 178.5(4) . . . . ?
C21 C22 C23 C28 -178.5(4) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C28 C23 C24 N3 -179.0(3) . . . . ?
C22 C23 C24 N3 1.9(4) . . . . ?
C28 C23 C24 C25 2.6(6) . . . . ?
C22 C23 C24 C25 -176.5(3) . . . . ?
N3 C24 C25 C26 -179.9(4) . . . . ?
C23 C24 C25 C26 -1.9(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C25 C26 C27 C28 0.3(7) . . . . ?
C26 C27 C28 C23 0.3(7) . . . . ?
C24 C23 C28 C27 -1.7(6) . . . . ?
C22 C23 C28 C27 177.1(4) . . . . ?
C22 C21 C29 C30 169.4(4) . . . . ?
N3 C21 C29 C30 -9.5(5) . . . . ?
C21 C29 C30 N4 -1.4(5) . . . . ?
C21 C29 C30 C31 -178.8(3) . . . . ?
C29 C30 C31 O3 -169.7(4) . . . . ?
N4 C30 C31 O3 12.7(5) . . . . ?
C29 C30 C31 O4 10.7(5) . . . . ?
N4 C30 C31 O4 -166.9(3) . . . . ?
N3 C34 C35 C40 20.8(4) . . . . ?
N4 C34 C35 C40 -99.9(4) . . . . ?
N3 C34 C35 C36 -161.5(3) . . . . ?
N4 C34 C35 C36 77.8(4) . . . . ?
C40 C35 C36 C37 1.7(5) . . . . ?
C34 C35 C36 C37 -176.1(3) . . . . ?
C40 C35 C36 Br2 -178.4(3) . . . . ?
C34 C35 C36 Br2 3.8(4) . . . . ?
C35 C36 C37 C38 0.2(5) . . . . ?
Br2 C36 C37 C38 -179.7(3) . . . . ?
C36 C37 C38 C39 -1.7(6) . . . . ?
C37 C38 C39 C40 1.3(6) . . . . ?
C36 C35 C40 C39 -2.2(5) . . . . ?
C34 C35 C40 C39 175.6(3) . . . . ?
C38 C39 C40 C35 0.8(6) . . . . ?
C5 C4 N1 C1 -176.6(4) . . . . ?
C3 C4 N1 C1 3.1(4) . . . . ?
C5 C4 N1 C14 -11.5(6) . . . . ?
C3 C4 N1 C14 168.2(3) . . . . ?
C2 C1 N1 C4 -3.1(4) . . . . ?
C9 C1 N1 C4 178.3(3) . . . . ?
C2 C1 N1 C14 -169.1(3) . . . . ?
C9 C1 N1 C14 12.4(5) . . . . ?
N2 C14 N1 C4 157.4(3) . . . . ?
C15 C14 N1 C4 -78.2(4) . . . . ?
N2 C14 N1 C1 -39.3(4) . . . . ?
C15 C14 N1 C1 85.1(4) . . . . ?
C9 C10 N2 C14 -31.9(5) . . . . ?
C11 C10 N2 C14 151.8(3) . . . . ?
N1 C14 N2 C10 47.6(4) . . . . ?
C15 C14 N2 C10 -77.1(4) . . . . ?
C25 C24 N3 C21 174.8(4) . . . . ?
C23 C24 N3 C21 -3.5(4) . . . . ?
C25 C24 N3 C34 9.3(6) . . . . ?
C23 C24 N3 C34 -169.0(3) . . . . ?
C22 C21 N3 C24 3.8(4) . . . . ?
C29 C21 N3 C24 -177.0(3) . . . . ?
C22 C21 N3 C34 170.0(3) . . . . ?
C29 C21 N3 C34 -10.9(5) . . . . ?
N4 C34 N3 C24 -159.3(3) . . . . ?
C35 C34 N3 C24 77.3(4) . . . . ?
N4 C34 N3 C21 37.1(4) . . . . ?
C35 C34 N3 C21 -86.3(4) . . . . ?
C29 C30 N4 C34 31.6(5) . . . . ?
C31 C30 N4 C34 -150.8(3) . . . . ?
N3 C34 N4 C30 -46.0(4) . . . . ?
C35 C34 N4 C30 78.1(4) . . . . ?
O1 C11 O2 C12 -0.8(5) . . . . ?
C10 C11 O2 C12 -179.7(3) . . . . ?
C13 C12 O2 C11 157.3(3) . . . . ?
O3 C31 O4 C32 1.4(6) . . . . ?
C30 C31 O4 C32 -179.0(3) . . . . ?
C33 C32 O4 C31 -160.3(4) . . . . ?

_refine_diff_density_max         0.632
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3

