# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_P21n
_database_code_depnum_ccdc_archive 'CCDC 1412619'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H36 Br2 N4 O4'
_chemical_formula_weight         892.63

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                   15.973(3)
_cell_length_b                   8.5673(15)
_cell_length_c                   28.865(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.316(4)
_cell_angle_gamma                90
_cell_volume                     3943.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.108
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25461
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.411
_diffrn_reflns_theta_max         25.990
_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             7741
_reflns_number_gt                6371
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0479P)²+6.2881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7741
_refine_ls_number_parameters     527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
Br1 Br 1.06051(2) 0.21395(5) 0.15872(2) 0.03080(12) Uani 1 1 d . . . . .
Br2 Br -0.06687(2) 0.45322(5) 0.35177(2) 0.03259(13) Uani 1 1 d . . . . .
O1 O 0.40103(19) 0.3096(3) -0.02403(8) 0.0345(7) Uani 1 1 d . . . . .
O2 O 0.31357(18) 0.8080(3) 0.02773(9) 0.0350(7) Uani 1 1 d . . . . .
O3 O 0.59206(18) -0.1718(3) 0.49344(9) 0.0300(6) Uani 1 1 d . . . . .
O4 O 0.68414(19) 0.3531(3) 0.51664(9) 0.0370(7) Uani 1 1 d . . . . .
N1 N 0.55662(18) 0.3626(3) 0.19365(9) 0.0182(6) Uani 1 1 d . . . . .
H1X H 0.5310 0.3445 0.2185 0.022 Uiso 1 1 d . U . . .
N2 N 0.38408(18) 0.3891(3) 0.22015(9) 0.0164(6) Uani 1 1 d . . . . .
N3 N 0.43505(18) 0.2942(3) 0.31480(9) 0.0177(6) Uani 1 1 d . . . . .
H3X H 0.4596 0.3035 0.2892 0.021 Uiso 1 1 d . U . . .
N4 N 0.60837(18) 0.2712(3) 0.28810(9) 0.0192(6) Uani 1 1 d . . . . .
C1 C 0.9503(2) 0.2387(4) 0.17906(12) 0.0214(8) Uani 1 1 d . . . . .
C2 C 0.8889(2) 0.1320(4) 0.16489(13) 0.0245(8) Uani 1 1 d . . . . .
H2 H 0.9015 0.0482 0.1460 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8082(2) 0.1520(4) 0.17925(12) 0.0240(8) Uani 1 1 d . . . . .
H3 H 0.7663 0.0822 0.1693 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7891(2) 0.2749(4) 0.20828(11) 0.0183(7) Uani 1 1 d . . . . .
C5 C 0.8524(2) 0.3794(4) 0.22241(12) 0.0216(8) Uani 1 1 d . . . . .
H5 H 0.8406 0.4610 0.2423 0.026 Uiso 1 1 calc R U . . .
C6 C 0.9326(2) 0.3635(4) 0.20733(12) 0.0219(8) Uani 1 1 d . . . . .
H6 H 0.9740 0.4357 0.2161 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7012(2) 0.2966(4) 0.22301(12) 0.0191(7) Uani 1 1 d . . . . .
C8 C 0.6406(2) 0.3443(4) 0.18859(11) 0.0187(7) Uani 1 1 d . . . . .
C9 C 0.6582(2) 0.3894(4) 0.14218(12) 0.0216(8) Uani 1 1 d . . . . .
H9 H 0.7103 0.3877 0.1294 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5846(2) 0.4349(4) 0.12052(11) 0.0198(8) Uani 1 1 d . . . . .
H10 H 0.5774 0.4723 0.0903 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5203(2) 0.4150(4) 0.15228(11) 0.0178(7) Uani 1 1 d . . . . .
C12 C 0.4341(2) 0.4434(4) 0.14219(11) 0.0175(7) Uani 1 1 d . . . . .
C13 C 0.4081(2) 0.4856(4) 0.09291(11) 0.0184(7) Uani 1 1 d . . . . .
C14 C 0.4202(2) 0.3757(4) 0.05808(11) 0.0210(8) Uani 1 1 d . . . . .
H14 H 0.4457 0.2806 0.0654 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3939(2) 0.4100(5) 0.01268(12) 0.0246(8) Uani 1 1 d . . . . .
C16 C 0.3552(2) 0.5517(4) 0.00133(11) 0.0217(8) Uani 1 1 d . . . . .
H16 H 0.3356 0.5721 -0.0290 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3464(2) 0.6615(5) 0.03573(12) 0.0240(8) Uani 1 1 d . . . . .
C18 C 0.3728(2) 0.6294(5) 0.08215(12) 0.0236(8) Uani 1 1 d . . . . .
H18 H 0.3667 0.7037 0.1052 0.028 Uiso 1 1 calc R U . . .
C19 C 0.4445(3) 0.1659(5) -0.01471(14) 0.0388(11) Uani 1 1 d . . . . .
H19A H 0.4473 0.1076 -0.0430 0.058 Uiso 1 1 calc R U . . .
H19B H 0.4152 0.1061 0.0073 0.058 Uiso 1 1 calc R U . . .
H19C H 0.5003 0.1877 -0.0022 0.058 Uiso 1 1 calc R U . . .
C20 C 0.2871(3) 0.8423(6) -0.02035(15) 0.0429(12) Uani 1 1 d . . . . .
H20A H 0.3350 0.8418 -0.0389 0.064 Uiso 1 1 calc R U . . .
H20B H 0.2609 0.9431 -0.0221 0.064 Uiso 1 1 calc R U . . .
H20C H 0.2478 0.7645 -0.0317 0.064 Uiso 1 1 calc R U . . .
C21 C 0.3713(2) 0.4286(4) 0.17391(11) 0.0166(7) Uani 1 1 d . . . . .
C22 C 0.2827(2) 0.4556(4) 0.16371(11) 0.0180(7) Uani 1 1 d . . . . .
H22 H 0.2573 0.4814 0.1349 0.022 Uiso 1 1 calc R U . . .
C23 C 0.2436(2) 0.4367(4) 0.20346(11) 0.0178(7) Uani 1 1 d . . . . .
H23 H 0.1866 0.4487 0.2073 0.021 Uiso 1 1 calc R U . . .
C24 C 0.3072(2) 0.3942(4) 0.23909(11) 0.0159(7) Uani 1 1 d . . . . .
C25 C 0.2916(2) 0.3675(4) 0.28594(11) 0.0160(7) Uani 1 1 d . . . . .
C26 C 0.2044(2) 0.3905(4) 0.30022(11) 0.0171(7) Uani 1 1 d . . . . .
C27 C 0.1399(2) 0.2869(4) 0.28614(11) 0.0192(7) Uani 1 1 d . . . . .
H27 H 0.1512 0.2054 0.2662 0.023 Uiso 1 1 calc R U . . .
C28 C 0.0590(2) 0.3038(4) 0.30154(11) 0.0209(8) Uani 1 1 d . . . . .
H28 H 0.0169 0.2330 0.2926 0.025 Uiso 1 1 calc R U . . .
C29 C 0.0428(2) 0.4281(4) 0.33032(12) 0.0219(8) Uani 1 1 d . . . . .
C30 C 0.1044(2) 0.5349(4) 0.34392(12) 0.0232(8) Uani 1 1 d . . . . .
H30 H 0.0924 0.6183 0.3631 0.028 Uiso 1 1 calc R U . . .
C31 C 0.1846(2) 0.5155(4) 0.32854(12) 0.0210(8) Uani 1 1 d . . . . .
H31 H 0.2260 0.5876 0.3373 0.025 Uiso 1 1 calc R U . . .
C32 C 0.3518(2) 0.3218(4) 0.32061(11) 0.0163(7) Uani 1 1 d . . . . .
C33 C 0.3359(2) 0.2917(4) 0.36858(11) 0.0199(7) Uani 1 1 d . . . . .
H33 H 0.2846 0.3010 0.3821 0.024 Uiso 1 1 calc R U . . .
C34 C 0.4100(2) 0.2473(4) 0.39036(12) 0.0206(8) Uani 1 1 d . . . . .
H34 H 0.4184 0.2206 0.4215 0.025 Uiso 1 1 calc R U . . .
C35 C 0.4727(2) 0.2490(4) 0.35683(11) 0.0175(7) Uani 1 1 d . . . . .
C36 C 0.5580(2) 0.2170(4) 0.36595(11) 0.0183(7) Uani 1 1 d . . . . .
C37 C 0.5853(2) 0.1693(4) 0.41477(11) 0.0184(7) Uani 1 1 d . . . . .
C38 C 0.5732(2) 0.0164(4) 0.42984(11) 0.0211(8) Uani 1 1 d . . . . .
H38 H 0.5477 -0.0571 0.4099 0.025 Uiso 1 1 calc R U . . .
C39 C 0.5995(2) -0.0247(4) 0.47491(12) 0.0226(8) Uani 1 1 d . . . . .
C40 C 0.6378(2) 0.0835(4) 0.50552(12) 0.0231(8) Uani 1 1 d . . . . .
H40 H 0.6553 0.0549 0.5356 0.028 Uiso 1 1 calc R U . . .
C41 C 0.6490(2) 0.2344(5) 0.48985(12) 0.0261(9) Uani 1 1 d . . . . .
C42 C 0.6230(2) 0.2781(4) 0.44459(12) 0.0227(8) Uani 1 1 d . . . . .
H42 H 0.6311 0.3799 0.4346 0.027 Uiso 1 1 calc R U . . .
C43 C 0.5556(3) -0.2906(5) 0.46462(14) 0.0321(9) Uani 1 1 d . . . . .
H43A H 0.4981 -0.2651 0.4565 0.048 Uiso 1 1 calc R U . . .
H43B H 0.5583 -0.3883 0.4809 0.048 Uiso 1 1 calc R U . . .
H43C H 0.5857 -0.2989 0.4369 0.048 Uiso 1 1 calc R U . . .
C44 C 0.7148(3) 0.3172(6) 0.56274(12) 0.0343(10) Uani 1 1 d . . . . .
H44A H 0.7560 0.2359 0.5619 0.051 Uiso 1 1 calc R U . . .
H44B H 0.6692 0.2829 0.5805 0.051 Uiso 1 1 calc R U . . .
H44C H 0.7398 0.4087 0.5769 0.051 Uiso 1 1 calc R U . . .
C45 C 0.6210(2) 0.2310(4) 0.33418(11) 0.0182(7) Uani 1 1 d . . . . .
C46 C 0.7091(2) 0.2022(4) 0.34470(12) 0.0216(8) Uani 1 1 d . . . . .
H46 H 0.7340 0.1749 0.3735 0.026 Uiso 1 1 calc R U . . .
C47 C 0.7489(2) 0.2222(4) 0.30512(12) 0.0221(8) Uani 1 1 d . . . . .
H47 H 0.8060 0.2100 0.3014 0.027 Uiso 1 1 calc R U . . .
C48 C 0.6855(2) 0.2664(4) 0.26943(12) 0.0196(7) 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
Br1 C1 1.899(4) . ?
Br2 C29 1.903(4) . ?
O1 C15 1.375(4) . ?
O1 C19 1.431(5) . ?
O2 C17 1.374(5) . ?
O2 C20 1.457(5) . ?
O3 C39 1.377(4) . ?
O3 C43 1.418(5) . ?
O4 C41 1.377(5) . ?
O4 C44 1.425(4) . ?
N1 C8 1.367(4) . ?
N1 C11 1.373(4) . ?
N1 H1X 0.8597 . ?
N2 C24 1.373(4) . ?
N2 C21 1.381(4) . ?
N3 C32 1.370(4) . ?
N3 C35 1.378(4) . ?
N3 H3X 0.8598 . ?
N4 C48 1.374(4) . ?
N4 C45 1.378(4) . ?
C1 C6 1.384(5) . ?
C1 C2 1.386(5) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(5) . ?
C4 C7 1.501(5) . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C48 1.401(5) . ?
C7 C8 1.407(5) . ?
C8 C9 1.437(5) . ?
C9 C10 1.356(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.426(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.411(5) . ?
C12 C21 1.403(5) . ?
C12 C13 1.503(4) . ?
C13 C18 1.382(5) . ?
C13 C14 1.399(5) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(5) . ?
C16 C17 1.381(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.409(5) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.447(5) . ?
C22 C23 1.347(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.450(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.408(4) . ?
C25 C32 1.403(4) . ?
C25 C26 1.488(5) . ?
C26 C31 1.395(5) . ?
C26 C27 1.402(5) . ?
C27 C28 1.399(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(5) . ?
C30 C31 1.389(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.445(4) . ?
C33 C34 1.362(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.432(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.399(5) . ?
C36 C45 1.406(5) . ?
C36 C37 1.507(4) . ?
C37 C42 1.384(5) . ?
C37 C38 1.397(5) . ?
C38 C39 1.389(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.397(5) . ?
C40 C41 1.385(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.398(5) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.444(5) . ?
C46 C47 1.350(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.452(5) . ?
C47 H47 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
C15 O1 C19 117.0(3) . . ?
C17 O2 C20 115.5(3) . . ?
C39 O3 C43 118.1(3) . . ?
C41 O4 C44 118.2(3) . . ?
C8 N1 C11 108.3(3) . . ?
C8 N1 H1X 125.9 . . ?
C11 N1 H1X 125.9 . . ?
C24 N2 C21 106.9(3) . . ?
C32 N3 C35 108.5(3) . . ?
C32 N3 H3X 125.7 . . ?
C35 N3 H3X 125.7 . . ?
C48 N4 C45 106.7(3) . . ?
C6 C1 C2 121.2(3) . . ?
C6 C1 Br1 119.6(3) . . ?
C2 C1 Br1 119.2(3) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C7 120.4(3) . . ?
C5 C4 C7 120.8(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C48 C7 C8 125.1(3) . . ?
C48 C7 C4 118.1(3) . . ?
C8 C7 C4 116.9(3) . . ?
N1 C8 C7 126.7(3) . . ?
N1 C8 C9 108.3(3) . . ?
C7 C8 C9 125.0(3) . . ?
C10 C9 C8 107.3(3) . . ?
C10 C9 H9 126.4 . . ?
C8 C9 H9 126.4 . . ?
C9 C10 C11 107.9(3) . . ?
C9 C10 H10 126.1 . . ?
C11 C10 H10 126.1 . . ?
N1 C11 C12 126.5(3) . . ?
N1 C11 C10 108.3(3) . . ?
C12 C11 C10 125.2(3) . . ?
C21 C12 C11 125.1(3) . . ?
C21 C12 C13 118.1(3) . . ?
C11 C12 C13 116.7(3) . . ?
C18 C13 C14 120.6(3) . . ?
C18 C13 C12 120.9(3) . . ?
C14 C13 C12 118.5(3) . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
O1 C15 C14 124.3(4) . . ?
O1 C15 C16 114.8(3) . . ?
C14 C15 C16 120.9(3) . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
O2 C17 C16 123.7(3) . . ?
O2 C17 C18 115.4(3) . . ?
C16 C17 C18 120.9(3) . . ?
C13 C18 C17 118.9(3) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C12 125.6(3) . . ?
N2 C21 C22 108.9(3) . . ?
C12 C21 C22 125.5(3) . . ?
C23 C22 C21 107.6(3) . . ?
C23 C22 H22 126.2 . . ?
C21 C22 H22 126.2 . . ?
C22 C23 C24 107.1(3) . . ?
C22 C23 H23 126.4 . . ?
C24 C23 H23 126.4 . . ?
N2 C24 C25 126.1(3) . . ?
N2 C24 C23 109.4(3) . . ?
C25 C24 C23 124.5(3) . . ?
C32 C25 C24 125.3(3) . . ?
C32 C25 C26 117.0(3) . . ?
C24 C25 C26 117.7(3) . . ?
C31 C26 C27 117.9(3) . . ?
C31 C26 C25 120.8(3) . . ?
C27 C26 C25 121.3(3) . . ?
C28 C27 C26 121.3(3) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C29 C28 C27 118.6(3) . . ?
C29 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
C28 C29 C30 121.6(3) . . ?
C28 C29 Br2 119.3(3) . . ?
C30 C29 Br2 119.1(3) . . ?
C29 C30 C31 118.9(3) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C30 C31 C26 121.6(3) . . ?
C30 C31 H31 119.2 . . ?
C26 C31 H31 119.2 . . ?
N3 C32 C25 126.2(3) . . ?
N3 C32 C33 108.2(3) . . ?
C25 C32 C33 125.5(3) . . ?
C34 C33 C32 107.2(3) . . ?
C34 C33 H33 126.4 . . ?
C32 C33 H33 126.4 . . ?
C33 C34 C35 108.0(3) . . ?
C33 C34 H34 126.0 . . ?
C35 C34 H34 126.0 . . ?
N3 C35 C36 126.2(3) . . ?
N3 C35 C34 108.1(3) . . ?
C36 C35 C34 125.6(3) . . ?
C35 C36 C45 125.9(3) . . ?
C35 C36 C37 117.1(3) . . ?
C45 C36 C37 117.0(3) . . ?
C42 C37 C38 120.1(3) . . ?
C42 C37 C36 119.4(3) . . ?
C38 C37 C36 120.5(3) . . ?
C39 C38 C37 119.3(3) . . ?
C39 C38 H38 120.4 . . ?
C37 C38 H38 120.4 . . ?
O3 C39 C38 124.5(3) . . ?
O3 C39 C40 114.0(3) . . ?
C38 C39 C40 121.5(3) . . ?
C41 C40 C39 118.2(3) . . ?
C41 C40 H40 120.9 . . ?
C39 C40 H40 120.9 . . ?
O4 C41 C40 124.2(3) . . ?
O4 C41 C42 114.6(3) . . ?
C40 C41 C42 121.2(3) . . ?
C37 C42 C41 119.7(3) . . ?
C37 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
O3 C43 H43A 109.5 . . ?
O3 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
O3 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O4 C44 H44A 109.5 . . ?
O4 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O4 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N4 C45 C36 125.5(3) . . ?
N4 C45 C46 109.4(3) . . ?
C36 C45 C46 125.1(3) . . ?
C47 C46 C45 107.5(3) . . ?
C47 C46 H46 126.2 . . ?
C45 C46 H46 126.2 . . ?
C46 C47 C48 106.9(3) . . ?
C46 C47 H47 126.5 . . ?
C48 C47 H47 126.5 . . ?
N4 C48 C7 125.7(3) . . ?
N4 C48 C47 109.5(3) . . ?
C7 C48 C47 124.8(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
C6 C1 C2 C3 0.4(5) . . . . ?
Br1 C1 C2 C3 -179.0(3) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C2 C3 C4 C7 179.1(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C7 C4 C5 C6 -177.3(3) . . . . ?
C4 C5 C6 C1 -2.2(5) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
Br1 C1 C6 C5 -179.2(3) . . . . ?
C3 C4 C7 C48 109.7(4) . . . . ?
C5 C4 C7 C48 -71.9(4) . . . . ?
C3 C4 C7 C8 -69.6(4) . . . . ?
C5 C4 C7 C8 108.8(4) . . . . ?
C11 N1 C8 C7 178.2(3) . . . . ?
C11 N1 C8 C9 0.9(4) . . . . ?
C48 C7 C8 N1 -3.1(6) . . . . ?
C4 C7 C8 N1 176.1(3) . . . . ?
C48 C7 C8 C9 173.8(4) . . . . ?
C4 C7 C8 C9 -7.0(5) . . . . ?
N1 C8 C9 C10 0.5(4) . . . . ?
C7 C8 C9 C10 -176.9(3) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
C8 N1 C11 C12 177.6(3) . . . . ?
C8 N1 C11 C10 -1.9(4) . . . . ?
C9 C10 C11 N1 2.2(4) . . . . ?
C9 C10 C11 C12 -177.3(3) . . . . ?
N1 C11 C12 C21 2.8(6) . . . . ?
C10 C11 C12 C21 -177.8(3) . . . . ?
N1 C11 C12 C13 -174.2(3) . . . . ?
C10 C11 C12 C13 5.2(5) . . . . ?
C21 C12 C13 C18 65.7(5) . . . . ?
C11 C12 C13 C18 -117.1(4) . . . . ?
C21 C12 C13 C14 -114.2(4) . . . . ?
C11 C12 C13 C14 63.0(4) . . . . ?
C18 C13 C14 C15 -2.3(5) . . . . ?
C12 C13 C14 C15 177.7(3) . . . . ?
C19 O1 C15 C14 -5.1(6) . . . . ?
C19 O1 C15 C16 176.6(3) . . . . ?
C13 C14 C15 O1 -178.6(3) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
O1 C15 C16 C17 -178.9(3) . . . . ?
C14 C15 C16 C17 2.7(5) . . . . ?
C20 O2 C17 C16 0.5(5) . . . . ?
C20 O2 C17 C18 179.3(3) . . . . ?
C15 C16 C17 O2 176.1(3) . . . . ?
C15 C16 C17 C18 -2.6(5) . . . . ?
C14 C13 C18 C17 2.4(5) . . . . ?
C12 C13 C18 C17 -177.5(3) . . . . ?
O2 C17 C18 C13 -178.8(3) . . . . ?
C16 C17 C18 C13 0.1(6) . . . . ?
C24 N2 C21 C12 177.4(3) . . . . ?
C24 N2 C21 C22 -1.4(4) . . . . ?
C11 C12 C21 N2 2.3(6) . . . . ?
C13 C12 C21 N2 179.3(3) . . . . ?
C11 C12 C21 C22 -179.2(3) . . . . ?
C13 C12 C21 C22 -2.2(5) . . . . ?
N2 C21 C22 C23 1.6(4) . . . . ?
C12 C21 C22 C23 -177.1(3) . . . . ?
C21 C22 C23 C24 -1.2(4) . . . . ?
C21 N2 C24 C25 -177.6(3) . . . . ?
C21 N2 C24 C23 0.7(4) . . . . ?
C22 C23 C24 N2 0.3(4) . . . . ?
C22 C23 C24 C25 178.6(3) . . . . ?
N2 C24 C25 C32 -4.0(6) . . . . ?
C23 C24 C25 C32 178.0(3) . . . . ?
N2 C24 C25 C26 175.5(3) . . . . ?
C23 C24 C25 C26 -2.5(5) . . . . ?
C32 C25 C26 C31 69.6(4) . . . . ?
C24 C25 C26 C31 -109.9(4) . . . . ?
C32 C25 C26 C27 -109.7(4) . . . . ?
C24 C25 C26 C27 70.8(4) . . . . ?
C31 C26 C27 C28 -2.8(5) . . . . ?
C25 C26 C27 C28 176.6(3) . . . . ?
C26 C27 C28 C29 1.6(5) . . . . ?
C27 C28 C29 C30 0.1(5) . . . . ?
C27 C28 C29 Br2 -179.9(2) . . . . ?
C28 C29 C30 C31 -0.6(5) . . . . ?
Br2 C29 C30 C31 179.5(3) . . . . ?
C29 C30 C31 C26 -0.7(5) . . . . ?
C27 C26 C31 C30 2.3(5) . . . . ?
C25 C26 C31 C30 -177.1(3) . . . . ?
C35 N3 C32 C25 -178.8(3) . . . . ?
C35 N3 C32 C33 -0.4(4) . . . . ?
C24 C25 C32 N3 -0.7(6) . . . . ?
C26 C25 C32 N3 179.8(3) . . . . ?
C24 C25 C32 C33 -178.9(3) . . . . ?
C26 C25 C32 C33 1.6(5) . . . . ?
N3 C32 C33 C34 0.2(4) . . . . ?
C25 C32 C33 C34 178.7(3) . . . . ?
C32 C33 C34 C35 0.0(4) . . . . ?
C32 N3 C35 C36 -176.9(3) . . . . ?
C32 N3 C35 C34 0.4(4) . . . . ?
C33 C34 C35 N3 -0.3(4) . . . . ?
C33 C34 C35 C36 177.1(3) . . . . ?
N3 C35 C36 C45 2.5(6) . . . . ?
C34 C35 C36 C45 -174.4(3) . . . . ?
N3 C35 C36 C37 180.0(3) . . . . ?
C34 C35 C36 C37 3.1(5) . . . . ?
C35 C36 C37 C42 -100.9(4) . . . . ?
C45 C36 C37 C42 76.8(4) . . . . ?
C35 C36 C37 C38 79.5(4) . . . . ?
C45 C36 C37 C38 -102.8(4) . . . . ?
C42 C37 C38 C39 -0.1(5) . . . . ?
C36 C37 C38 C39 179.5(3) . . . . ?
C43 O3 C39 C38 0.5(5) . . . . ?
C43 O3 C39 C40 -178.6(3) . . . . ?
C37 C38 C39 O3 -179.0(3) . . . . ?
C37 C38 C39 C40 0.0(6) . . . . ?
O3 C39 C40 C41 179.3(3) . . . . ?
C38 C39 C40 C41 0.1(6) . . . . ?
C44 O4 C41 C40 3.2(6) . . . . ?
C44 O4 C41 C42 -178.0(3) . . . . ?
C39 C40 C41 O4 178.6(4) . . . . ?
C39 C40 C41 C42 -0.2(6) . . . . ?
C38 C37 C42 C41 0.0(5) . . . . ?
C36 C37 C42 C41 -179.6(3) . . . . ?
O4 C41 C42 C37 -178.7(3) . . . . ?
C40 C41 C42 C37 0.1(6) . . . . ?
C48 N4 C45 C36 -178.1(3) . . . . ?
C48 N4 C45 C46 0.8(4) . . . . ?
C35 C36 C45 N4 -3.4(6) . . . . ?
C37 C36 C45 N4 179.1(3) . . . . ?
C35 C36 C45 C46 177.9(3) . . . . ?
C37 C36 C45 C46 0.4(5) . . . . ?
N4 C45 C46 C47 -1.1(4) . . . . ?
C36 C45 C46 C47 177.8(3) . . . . ?
C45 C46 C47 C48 0.9(4) . . . . ?
C45 N4 C48 C7 178.7(3) . . . . ?
C45 N4 C48 C47 -0.2(4) . . . . ?
C8 C7 C48 N4 3.3(6) . . . . ?
C4 C7 C48 N4 -175.9(3) . . . . ?
C8 C7 C48 C47 -177.8(3) . . . . ?
C4 C7 C48 C47 2.9(5) . . . . ?
C46 C47 C48 N4 -0.4(4) . . . . ?
C46 C47 C48 C7 -179.4(4) . . . . ?

_refine_diff_density_max         1.046
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_trans4p
_database_code_depnum_ccdc_archive 'CCDC 1412620'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H36 Br2 N4 O4'
_chemical_formula_weight         892.63

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   23.99(3)
_cell_length_b                   16.08(3)
_cell_length_c                   10.433(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.51(7)
_cell_angle_gamma                90
_cell_volume                     3929(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    74
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.0

_exptl_crystal_description       Needle
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    2.116
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11841
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_av_R_equivalents  0.1491
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3666
_reflns_number_gt                3168
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+27.0327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3666
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.2160
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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
Br1 Br 0.72696(3) 0.17077(5) 0.23298(7) 0.0457(3) Uani 1 1 d . . . . .
O1 O 0.7357(2) 0.9295(3) 0.1815(5) 0.0451(13) Uani 1 1 d . . . . .
O2 O 0.5673(2) 0.9118(3) 0.3575(5) 0.0487(13) Uani 1 1 d . . . . .
H2X H 0.5392 0.6040 -0.1671 0.058 Uiso 1 1 d . U . . .
N1 N 0.5000 0.4799(4) -0.2500 0.0275(16) Uani 1 2 d S T P . .
N2 N 0.5644(2) 0.6077(3) -0.0846(5) 0.0275(11) Uani 1 1 d . . . . .
N3 N 0.5000 0.7374(4) -0.2500 0.0300(17) Uani 1 2 d S T P . .
C1 C 0.5232(3) 0.3429(4) -0.2001(7) 0.0321(15) Uani 1 1 d . . . . .
H1 H 0.5429 0.2954 -0.1593 0.039 Uiso 1 1 calc R U . . .
C2 C 0.5372(2) 0.4297(4) -0.1665(6) 0.0279(13) Uani 1 1 d . . . . .
C3 C 0.5807(2) 0.4564(4) -0.0613(6) 0.0273(13) Uani 1 1 d . . . . .
C4 C 0.6174(3) 0.3892(4) 0.0144(6) 0.0281(13) Uani 1 1 d . . . . .
C5 C 0.5935(3) 0.3321(4) 0.0873(7) 0.0347(15) Uani 1 1 d . . . . .
H5 H 0.5547 0.3379 0.0927 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6255(3) 0.2668(4) 0.1524(7) 0.0394(16) Uani 1 1 d . . . . .
H6 H 0.6088 0.2272 0.2004 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6830(3) 0.2608(4) 0.1454(6) 0.0338(15) Uani 1 1 d . . . . .
C8 C 0.7078(3) 0.3181(4) 0.0754(7) 0.0348(15) Uani 1 1 d . . . . .
H8 H 0.7470 0.3134 0.0725 0.042 Uiso 1 1 calc R U . . .
C9 C 0.6749(3) 0.3826(4) 0.0095(6) 0.0330(15) Uani 1 1 d . . . . .
H9 H 0.6915 0.4221 -0.0388 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5906(3) 0.5391(4) -0.0224(6) 0.0280(13) Uani 1 1 d . . . . .
C11 C 0.6287(2) 0.5647(4) 0.0987(6) 0.0304(14) Uani 1 1 d . . . . .
H11 H 0.6520 0.5295 0.1614 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6245(3) 0.6489(4) 0.1052(6) 0.0308(14) Uani 1 1 d . . . . .
H12 H 0.6445 0.6836 0.1735 0.037 Uiso 1 1 calc R U . . .
C13 C 0.5840(3) 0.6759(4) -0.0107(6) 0.0290(14) Uani 1 1 d . . . . .
C14 C 0.5695(3) 0.7594(4) -0.0399(6) 0.0306(14) Uani 1 1 d . . . . .
C15 C 0.5978(3) 0.8223(4) 0.0598(6) 0.0312(14) Uani 1 1 d . . . . .
C16 C 0.6539(3) 0.8480(4) 0.0648(7) 0.0310(14) Uani 1 1 d . . . . .
H16 H 0.6734 0.8314 -0.0012 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6805(3) 0.8982(4) 0.1680(7) 0.0379(17) Uani 1 1 d . . . . .
C18 C 0.6533(3) 0.9222(4) 0.2679(7) 0.0369(16) Uani 1 1 d . . . . .
H18 H 0.6725 0.9561 0.3384 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5977(3) 0.8956(4) 0.2623(7) 0.0399(17) Uani 1 1 d . . . . .
C20 C 0.5688(3) 0.8472(4) 0.1566(7) 0.0362(16) Uani 1 1 d . . . . .
H20 H 0.5302 0.8314 0.1508 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5309(2) 0.7872(4) -0.1539(6) 0.0285(13) Uani 1 1 d . . . . .
C22 C 0.5182(3) 0.8731(4) -0.1914(7) 0.0344(15) Uani 1 1 d . . . . .
H22 H 0.5329 0.9208 -0.1417 0.041 Uiso 1 1 calc R U . . .
C23 C 0.7690(3) 0.9007(5) 0.0918(8) 0.050(2) Uani 1 1 d . . . . .
H23A H 0.7681 0.8398 0.0887 0.075 Uiso 1 1 calc R U . . .
H23B H 0.8085 0.9196 0.1214 0.075 Uiso 1 1 calc R U . . .
H23C H 0.7532 0.9230 0.0041 0.075 Uiso 1 1 calc R U . . .
C24 C 0.5985(3) 0.9414(5) 0.4810(7) 0.0480(19) Uani 1 1 d . . . . .
H24A H 0.6296 0.9028 0.5160 0.072 Uiso 1 1 calc R U . . .
H24B H 0.5730 0.9456 0.5424 0.072 Uiso 1 1 calc R U . . .
H24C H 0.6144 0.9964 0.4695 0.072 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
Br1 C7 1.904(7) . ?
O1 C17 1.394(8) . ?
O1 C23 1.432(10) . ?
O2 C19 1.380(9) . ?
O2 C24 1.425(8) . ?
N1 C2 1.368(7) . ?
N1 C2 1.368(7) 2_654 ?
N2 C10 1.363(8) . ?
N2 C13 1.365(8) . ?
N2 H2X 0.9404 . ?
N3 C21 1.369(7) . ?
N3 C21 1.369(7) 2_654 ?
C1 C1 1.348(12) 2_654 ?
C1 C2 1.461(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(8) . ?
C3 C10 1.395(9) . ?
C3 C4 1.505(8) . ?
C4 C5 1.392(9) . ?
C4 C9 1.396(9) . ?
C5 C6 1.388(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(10) . ?
C8 C9 1.392(9) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.449(9) . ?
C11 C12 1.361(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.444(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.403(9) . ?
C14 C21 1.413(8) . ?
C14 C15 1.503(8) . ?
C15 C16 1.397(9) . ?
C15 C20 1.403(10) . ?
C16 C17 1.385(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(10) . ?
C18 C19 1.389(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.450(9) . ?
C22 C22 1.339(13) 2_654 ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C17 O1 C23 117.9(6) . . ?
C19 O2 C24 117.2(6) . . ?
C2 N1 C2 107.6(7) . 2_654 ?
C10 N2 C13 108.4(5) . . ?
C10 N2 H2X 121.5 . . ?
C13 N2 H2X 130.0 . . ?
C21 N3 C21 108.4(7) . 2_654 ?
C1 C1 C2 107.1(3) 2_654 . ?
C1 C1 H1 126.4 2_654 . ?
C2 C1 H1 126.4 . . ?
N1 C2 C3 126.0(6) . . ?
N1 C2 C1 109.0(5) . . ?
C3 C2 C1 125.0(5) . . ?
C10 C3 C2 124.7(5) . . ?
C10 C3 C4 119.2(5) . . ?
C2 C3 C4 116.1(5) . . ?
C5 C4 C9 119.8(6) . . ?
C5 C4 C3 119.8(5) . . ?
C9 C4 C3 120.3(6) . . ?
C6 C5 C4 121.1(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 118.2(6) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C8 C7 C6 121.4(6) . . ?
C8 C7 Br1 120.1(5) . . ?
C6 C7 Br1 118.5(5) . . ?
C7 C8 C9 119.5(6) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C4 119.9(6) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
N2 C10 C3 126.9(6) . . ?
N2 C10 C11 108.9(5) . . ?
C3 C10 C11 124.1(6) . . ?
C12 C11 C10 106.7(5) . . ?
C12 C11 H11 126.7 . . ?
C10 C11 H11 126.7 . . ?
C11 C12 C13 107.5(5) . . ?
C11 C12 H12 126.2 . . ?
C13 C12 H12 126.2 . . ?
N2 C13 C14 127.4(6) . . ?
N2 C13 C12 108.5(5) . . ?
C14 C13 C12 124.0(6) . . ?
C13 C14 C21 124.9(6) . . ?
C13 C14 C15 116.1(5) . . ?
C21 C14 C15 119.0(5) . . ?
C16 C15 C20 120.8(6) . . ?
C16 C15 C14 120.8(6) . . ?
C20 C15 C14 118.0(6) . . ?
C17 C16 C15 118.7(6) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 O1 123.8(7) . . ?
C16 C17 C18 121.9(6) . . ?
O1 C17 C18 114.2(6) . . ?
C19 C18 C17 118.8(6) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
O2 C19 C18 124.4(6) . . ?
O2 C19 C20 114.9(6) . . ?
C18 C19 C20 120.7(7) . . ?
C15 C20 C19 119.1(6) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
N3 C21 C14 125.7(6) . . ?
N3 C21 C22 108.1(5) . . ?
C14 C21 C22 126.1(5) . . ?
C22 C22 C21 107.7(3) 2_654 . ?
C22 C22 H22 126.2 2_654 . ?
C21 C22 H22 126.2 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C2 N1 C2 C3 -176.8(8) 2_654 . . . ?
C2 N1 C2 C1 0.7(3) 2_654 . . . ?
C1 C1 C2 N1 -1.9(9) 2_654 . . . ?
C1 C1 C2 C3 175.6(7) 2_654 . . . ?
N1 C2 C3 C10 3.2(10) . . . . ?
C1 C2 C3 C10 -173.9(6) . . . . ?
N1 C2 C3 C4 -178.3(5) . . . . ?
C1 C2 C3 C4 4.6(9) . . . . ?
C10 C3 C4 C5 112.6(7) . . . . ?
C2 C3 C4 C5 -66.0(8) . . . . ?
C10 C3 C4 C9 -68.9(8) . . . . ?
C2 C3 C4 C9 112.6(7) . . . . ?
C9 C4 C5 C6 -2.0(10) . . . . ?
C3 C4 C5 C6 176.5(6) . . . . ?
C4 C5 C6 C7 1.5(10) . . . . ?
C5 C6 C7 C8 -0.1(10) . . . . ?
C5 C6 C7 Br1 -179.4(5) . . . . ?
C6 C7 C8 C9 -0.7(10) . . . . ?
Br1 C7 C8 C9 178.6(5) . . . . ?
C7 C8 C9 C4 0.1(10) . . . . ?
C5 C4 C9 C8 1.2(10) . . . . ?
C3 C4 C9 C8 -177.3(6) . . . . ?
C13 N2 C10 C3 176.6(6) . . . . ?
C13 N2 C10 C11 0.6(7) . . . . ?
C2 C3 C10 N2 -6.5(10) . . . . ?
C4 C3 C10 N2 175.1(6) . . . . ?
C2 C3 C10 C11 168.9(6) . . . . ?
C4 C3 C10 C11 -9.5(9) . . . . ?
N2 C10 C11 C12 -0.5(7) . . . . ?
C3 C10 C11 C12 -176.6(6) . . . . ?
C10 C11 C12 C13 0.1(7) . . . . ?
C10 N2 C13 C14 178.0(6) . . . . ?
C10 N2 C13 C12 -0.5(7) . . . . ?
C11 C12 C13 N2 0.2(7) . . . . ?
C11 C12 C13 C14 -178.4(6) . . . . ?
N2 C13 C14 C21 0.3(11) . . . . ?
C12 C13 C14 C21 178.7(6) . . . . ?
N2 C13 C14 C15 -179.9(6) . . . . ?
C12 C13 C14 C15 -1.6(10) . . . . ?
C13 C14 C15 C16 79.5(8) . . . . ?
C21 C14 C15 C16 -100.8(7) . . . . ?
C13 C14 C15 C20 -93.4(7) . . . . ?
C21 C14 C15 C20 86.3(8) . . . . ?
C20 C15 C16 C17 0.4(9) . . . . ?
C14 C15 C16 C17 -172.3(6) . . . . ?
C15 C16 C17 O1 -178.1(6) . . . . ?
C15 C16 C17 C18 1.3(10) . . . . ?
C23 O1 C17 C16 -7.3(9) . . . . ?
C23 O1 C17 C18 173.2(6) . . . . ?
C16 C17 C18 C19 -0.8(10) . . . . ?
O1 C17 C18 C19 178.7(6) . . . . ?
C24 O2 C19 C18 -14.2(10) . . . . ?
C24 O2 C19 C20 164.3(6) . . . . ?
C17 C18 C19 O2 176.9(6) . . . . ?
C17 C18 C19 C20 -1.5(10) . . . . ?
C16 C15 C20 C19 -2.6(9) . . . . ?
C14 C15 C20 C19 170.3(6) . . . . ?
O2 C19 C20 C15 -175.4(6) . . . . ?
C18 C19 C20 C15 3.2(10) . . . . ?
C21 N3 C21 C14 -177.9(8) 2_654 . . . ?
C21 N3 C21 C22 0.6(3) 2_654 . . . ?
C13 C14 C21 N3 2.9(10) . . . . ?
C15 C14 C21 N3 -176.8(5) . . . . ?
C13 C14 C21 C22 -175.3(7) . . . . ?
C15 C14 C21 C22 5.0(10) . . . . ?
N3 C21 C22 C22 -1.6(9) . . . 2_654 ?
C14 C21 C22 C22 176.8(7) . . . 2_654 ?

_refine_diff_density_max         1.427
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.108

_shelxl_version_number           2013-4

