# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_bwn16012
_database_code_depnum_ccdc_archive 'CCDC 1470553'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(R,E)-tert-butyl 3-(4-bromobenzylidene)-4-((S)-1-(4-methoxyphenyl)-2-nitroethyl)-2,5-dioxopyrrolidine-1-carboxylate '
_chemical_name_common            ?
_chemical_melting_point          401-403
_chemical_formula_moiety         'C25 H25 Br N2 O7'
_chemical_formula_sum            'C25 H25 Br N2 O7'
_chemical_formula_weight         545.38
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   11.689(2)
_cell_length_b                   17.969(4)
_cell_length_c                   12.350(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.44(3)
_cell_angle_gamma                90.00
_cell_volume                     2593.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7952
_cell_measurement_theta_min      1.6489
_cell_measurement_theta_max      27.4816

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    1.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7306
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16824
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.67
_reflns_number_total             9172
_reflns_number_gt                8148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0935P)²+0.2425P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(9)
_refine_ls_number_reflns         9172
_refine_ls_number_parameters     639
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.36152(6) 0.53578(5) 0.37203(6) 0.0627(2) Uani 1 1 d . . .
O1 O 0.6035(4) 0.3818(3) 1.0281(4) 0.0497(12) Uani 1 1 d . . .
O2 O 0.3004(3) 0.2236(2) 1.0064(3) 0.0375(9) Uani 1 1 d . . .
O3 O 0.5621(4) 0.2461(3) 1.1768(4) 0.0497(12) Uani 1 1 d . . .
O4 O 0.3863(3) 0.2929(2) 1.2098(3) 0.0330(8) Uani 1 1 d . . .
O5 O 0.3325(5) 0.1690(4) 0.5908(4) 0.0661(15) Uani 1 1 d . . .
O6 O 0.3393(5) 0.0710(3) 0.6900(5) 0.0643(15) Uani 1 1 d . . .
O7 O 0.8694(3) 0.1826(3) 0.7216(4) 0.0436(10) Uani 1 1 d . . .
N1 N 0.4541(3) 0.2991(3) 1.0411(3) 0.0297(9) Uani 1 1 d . . .
N2 N 0.3339(4) 0.1381(3) 0.6786(4) 0.0397(12) Uani 1 1 d . . .
C1 C 0.4045(5) 0.4975(3) 0.5102(5) 0.0395(13) Uani 1 1 d . . .
C2 C 0.5177(5) 0.5068(3) 0.5436(5) 0.0400(13) Uani 1 1 d . . .
H2 H 0.5726 0.5302 0.4986 0.048 Uiso 1 1 calc R . .
C3 C 0.5464(4) 0.4805(3) 0.6457(5) 0.0349(12) Uani 1 1 d . . .
H3 H 0.6223 0.4878 0.6716 0.042 Uiso 1 1 calc R . .
C4 C 0.4686(4) 0.4440(3) 0.7119(4) 0.0284(10) Uani 1 1 d . . .
C5 C 0.3565(4) 0.4364(3) 0.6737(5) 0.0345(12) Uani 1 1 d . . .
H5 H 0.3014 0.4123 0.7177 0.041 Uiso 1 1 calc R . .
C6 C 0.3238(4) 0.4633(3) 0.5731(5) 0.0386(13) Uani 1 1 d . . .
H6 H 0.2471 0.4582 0.5481 0.046 Uiso 1 1 calc R . .
C7 C 0.5067(4) 0.4187(3) 0.8174(4) 0.0308(11) Uani 1 1 d . . .
H7 H 0.5715 0.4443 0.8456 0.037 Uiso 1 1 calc R . .
C8 C 0.4656(4) 0.3652(3) 0.8817(4) 0.0266(10) Uani 1 1 d . . .
C9 C 0.5195(5) 0.3528(3) 0.9877(5) 0.0342(12) Uani 1 1 d . . .
C10 C 0.3665(4) 0.2700(3) 0.9768(4) 0.0259(10) Uani 1 1 d . . .
C11 C 0.3733(4) 0.3083(3) 0.8666(4) 0.0252(10) Uani 1 1 d . . .
H11 H 0.2992 0.3342 0.8512 0.030 Uiso 1 1 calc R . .
C12 C 0.3997(4) 0.2528(3) 0.7719(4) 0.0250(9) Uani 1 1 d . . .
H12 H 0.3792 0.2789 0.7029 0.030 Uiso 1 1 calc R . .
C13 C 0.3233(4) 0.1838(3) 0.7784(4) 0.0281(10) Uani 1 1 d . . .
H13A H 0.3457 0.1537 0.8422 0.034 Uiso 1 1 calc R . .
H13B H 0.2426 0.1993 0.7874 0.034 Uiso 1 1 calc R . .
C14 C 0.5258(4) 0.2326(3) 0.7648(4) 0.0264(10) Uani 1 1 d . . .
C15 C 0.5786(4) 0.1812(3) 0.8317(4) 0.0294(11) Uani 1 1 d . . .
H15 H 0.5346 0.1572 0.8859 0.035 Uiso 1 1 calc R . .
C16 C 0.6936(4) 0.1633(3) 0.8223(4) 0.0324(11) Uani 1 1 d . . .
H16 H 0.7278 0.1283 0.8702 0.039 Uiso 1 1 calc R . .
C17 C 0.7584(4) 0.1974(3) 0.7417(5) 0.0325(11) Uani 1 1 d . . .
C18 C 0.7072(4) 0.2504(3) 0.6746(4) 0.0293(10) Uani 1 1 d . . .
H18 H 0.7510 0.2748 0.6207 0.035 Uiso 1 1 calc R . .
C19 C 0.5934(4) 0.2674(3) 0.6865(4) 0.0271(10) Uani 1 1 d . . .
H19 H 0.5596 0.3037 0.6403 0.033 Uiso 1 1 calc R . .
C20 C 0.9192(5) 0.1181(4) 0.7696(6) 0.0520(17) Uani 1 1 d . . .
H20A H 0.9232 0.1246 0.8483 0.078 Uiso 1 1 calc R . .
H20B H 0.9964 0.1109 0.7412 0.078 Uiso 1 1 calc R . .
H20C H 0.8721 0.0745 0.7523 0.078 Uiso 1 1 calc R . .
C21 C 0.4746(4) 0.2757(3) 1.1498(4) 0.0308(11) Uani 1 1 d . . .
C22 C 0.3759(5) 0.2644(4) 1.3232(4) 0.0406(14) Uani 1 1 d . . .
C23 C 0.4730(6) 0.2948(5) 1.3923(5) 0.062(2) Uani 1 1 d . . .
H23A H 0.5444 0.2696 1.3734 0.093 Uiso 1 1 calc R . .
H23B H 0.4564 0.2862 1.4690 0.093 Uiso 1 1 calc R . .
H23C H 0.4810 0.3484 1.3794 0.093 Uiso 1 1 calc R . .
C24 C 0.3715(8) 0.1803(4) 1.3177(6) 0.063(2) Uani 1 1 d . . .
H24A H 0.3148 0.1650 1.2632 0.094 Uiso 1 1 calc R . .
H24B H 0.3500 0.1604 1.3885 0.094 Uiso 1 1 calc R . .
H24C H 0.4469 0.1611 1.2977 0.094 Uiso 1 1 calc R . .
C25 C 0.2615(6) 0.2971(5) 1.3591(5) 0.0516(17) Uani 1 1 d . . .
H25A H 0.2636 0.3514 1.3522 0.077 Uiso 1 1 calc R . .
H25B H 0.2476 0.2836 1.4347 0.077 Uiso 1 1 calc R . .
H25C H 0.1998 0.2771 1.3133 0.077 Uiso 1 1 calc R . .
Br2 Br 0.86814(7) 0.15765(4) 1.43258(5) 0.0574(2) Uani 1 1 d . . .
O8 O 0.8016(3) 0.4444(2) 0.7797(3) 0.0338(8) Uani 1 1 d . . .
O9 O 1.1030(3) 0.2838(3) 0.7602(3) 0.0397(9) Uani 1 1 d . . .
O10 O 1.0696(4) 0.4227(4) 0.6194(4) 0.0626(15) Uani 1 1 d . . .
O11 O 0.8910(3) 0.3842(2) 0.5728(3) 0.0300(8) Uani 1 1 d . . .
O12 O 0.8483(3) 0.5953(2) 1.0909(4) 0.0394(9) Uani 1 1 d . . .
O13 O 0.8709(4) 0.5003(3) 1.1950(3) 0.0481(11) Uani 1 1 d . . .
O14 O 1.3640(3) 0.5263(2) 0.9828(4) 0.0438(10) Uani 1 1 d . . .
N3 N 0.9528(3) 0.3662(2) 0.7429(3) 0.0275(9) Uani 1 1 d . . .
N4 N 0.8501(3) 0.5283(2) 1.1069(3) 0.0286(9) Uani 1 1 d . . .
C26 C 0.9088(5) 0.1835(3) 1.2898(5) 0.0358(12) Uani 1 1 d . . .
C27 C 1.0180(4) 0.1672(3) 1.2508(5) 0.0366(12) Uani 1 1 d . . .
H27 H 1.0723 0.1421 1.2951 0.044 Uiso 1 1 calc R . .
C28 C 1.0449(4) 0.1881(3) 1.1478(4) 0.0314(11) Uani 1 1 d . . .
H28 H 1.1184 0.1760 1.1206 0.038 Uiso 1 1 calc R . .
C29 C 0.9678(4) 0.2270(3) 1.0805(4) 0.0281(10) Uani 1 1 d . . .
C30 C 0.8586(4) 0.2417(3) 1.1213(4) 0.0309(11) Uani 1 1 d . . .
H30 H 0.8042 0.2670 1.0773 0.037 Uiso 1 1 calc R . .
C31 C 0.8287(5) 0.2199(3) 1.2254(5) 0.0334(11) Uani 1 1 d . . .
H31 H 0.7542 0.2298 1.2521 0.040 Uiso 1 1 calc R . .
C32 C 1.0061(4) 0.2477(3) 0.9716(4) 0.0260(10) Uani 1 1 d . . .
H32 H 1.0686 0.2196 0.9446 0.031 Uiso 1 1 calc R . .
C33 C 0.9656(4) 0.3007(3) 0.9043(4) 0.0268(10) Uani 1 1 d . . .
C34 C 1.0189(4) 0.3119(3) 0.7970(4) 0.0296(11) Uani 1 1 d . . .
C35 C 0.8663(4) 0.3960(3) 0.8070(4) 0.0292(11) Uani 1 1 d . . .
C36 C 0.8738(4) 0.3595(3) 0.9183(4) 0.0246(10) Uani 1 1 d . . .
H36 H 0.7992 0.3357 0.9371 0.030 Uiso 1 1 calc R . .
C37 C 0.9098(4) 0.4163(3) 1.0075(4) 0.0274(10) Uani 1 1 d . . .
H37 H 0.9077 0.3890 1.0780 0.033 Uiso 1 1 calc R . .
C38 C 0.8204(4) 0.4788(3) 1.0151(4) 0.0275(10) Uani 1 1 d . . .
H38A H 0.8189 0.5078 0.9469 0.033 Uiso 1 1 calc R . .
H38B H 0.7435 0.4572 1.0261 0.033 Uiso 1 1 calc R . .
C39 C 1.0304(4) 0.4455(3) 0.9957(4) 0.0264(10) Uani 1 1 d . . .
C40 C 1.0595(4) 0.4982(3) 0.9186(4) 0.0315(11) Uani 1 1 d . . .
H40 H 1.0023 0.5161 0.8702 0.038 Uiso 1 1 calc R . .
C41 C 1.1704(5) 0.5255(3) 0.9103(5) 0.0351(11) Uani 1 1 d . . .
H41 H 1.1883 0.5607 0.8557 0.042 Uiso 1 1 calc R . .
C42 C 1.2546(4) 0.5015(3) 0.9812(5) 0.0328(11) Uani 1 1 d . . .
C43 C 1.2267(4) 0.4482(3) 1.0596(5) 0.0353(12) Uani 1 1 d . . .
H43 H 1.2840 0.4309 1.1084 0.042 Uiso 1 1 calc R . .
C44 C 1.1172(4) 0.4208(3) 1.0664(4) 0.0310(11) Uani 1 1 d . . .
H44 H 1.0999 0.3846 1.1198 0.037 Uiso 1 1 calc R . .
C45 C 1.3920(5) 0.5830(4) 0.9102(5) 0.0454(15) Uani 1 1 d . . .
H45A H 1.3477 0.6278 0.9274 0.068 Uiso 1 1 calc R . .
H45B H 1.3740 0.5670 0.8362 0.068 Uiso 1 1 calc R . .
H45C H 1.4739 0.5942 0.9162 0.068 Uiso 1 1 calc R . .
C46 C 0.9794(4) 0.3948(3) 0.6374(4) 0.0320(11) Uani 1 1 d . . .
C47 C 0.8886(4) 0.4193(3) 0.4628(4) 0.0320(11) Uani 1 1 d . . .
C48 C 0.9839(5) 0.3892(4) 0.3961(5) 0.0471(16) Uani 1 1 d . . .
H48A H 1.0570 0.4083 0.4237 0.071 Uiso 1 1 calc R . .
H48B H 0.9734 0.4047 0.3207 0.071 Uiso 1 1 calc R . .
H48C H 0.9838 0.3347 0.4002 0.071 Uiso 1 1 calc R . .
C49 C 0.7752(5) 0.3930(4) 0.4192(5) 0.0382(13) Uani 1 1 d . . .
H49A H 0.7743 0.3385 0.4171 0.057 Uiso 1 1 calc R . .
H49B H 0.7636 0.4125 0.3458 0.057 Uiso 1 1 calc R . .
H49C H 0.7137 0.4108 0.4661 0.057 Uiso 1 1 calc R . .
C50 C 0.8917(6) 0.5025(4) 0.4761(5) 0.0435(14) Uani 1 1 d . . .
H50A H 0.8327 0.5178 0.5276 0.065 Uiso 1 1 calc R . .
H50B H 0.8772 0.5263 0.4059 0.065 Uiso 1 1 calc R . .
H50C H 0.9671 0.5176 0.5035 0.065 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 C1 1.904(6) . ?
O1 C9 1.216(6) . ?
O2 C10 1.194(6) . ?
O3 C21 1.197(6) . ?
O4 C21 1.312(6) . ?
O4 C22 1.497(7) . ?
O5 N2 1.218(7) . ?
O6 N2 1.216(7) . ?
O7 C17 1.349(6) . ?
O7 C20 1.424(8) . ?
N1 C10 1.394(6) . ?
N1 C9 1.399(7) . ?
N1 C21 1.425(6) . ?
N2 C13 1.487(7) . ?
C1 C6 1.371(8) . ?
C1 C2 1.393(8) . ?
C2 C3 1.385(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(7) . ?
C4 C7 1.446(7) . ?
C5 C6 1.385(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.339(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.465(7) . ?
C8 C11 1.497(7) . ?
C10 C11 1.528(7) . ?
C11 C12 1.570(7) . ?
C11 H11 1.0000 . ?
C12 C14 1.521(7) . ?
C12 C13 1.530(7) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.382(7) . ?
C14 C19 1.401(7) . ?
C15 C16 1.388(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(8) . ?
C18 C19 1.374(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 C24 1.514(10) . ?
C22 C23 1.517(8) . ?
C22 C25 1.529(8) . ?
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 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
Br2 C26 1.887(6) . ?
O8 C35 1.201(6) . ?
O9 C34 1.198(6) . ?
O10 C46 1.190(6) . ?
O11 C46 1.315(6) . ?
O11 C47 1.498(6) . ?
O12 N4 1.220(6) . ?
O13 N4 1.222(6) . ?
O14 C42 1.354(6) . ?
O14 C45 1.398(8) . ?
N3 C35 1.395(7) . ?
N3 C34 1.410(6) . ?
N3 C46 1.437(7) . ?
N4 C38 1.481(7) . ?
C26 C31 1.388(8) . ?
C26 C27 1.398(8) . ?
C27 C28 1.365(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.407(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.402(7) . ?
C29 C32 1.469(7) . ?
C30 C31 1.391(8) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.347(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.482(7) . ?
C33 C36 1.517(7) . ?
C35 C36 1.525(7) . ?
C36 C37 1.558(7) . ?
C36 H36 1.0000 . ?
C37 C39 1.512(7) . ?
C37 C38 1.537(7) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.387(7) . ?
C39 C44 1.406(6) . ?
C40 C41 1.390(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.382(7) . ?
C41 H41 0.9500 . ?
C42 C43 1.402(8) . ?
C43 C44 1.374(7) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C47 C48 1.492(7) . ?
C47 C50 1.504(9) . ?
C47 C49 1.504(7) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 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
C21 O4 C22 121.2(4) . . ?
C17 O7 C20 118.2(5) . . ?
C10 N1 C9 113.0(4) . . ?
C10 N1 C21 122.9(4) . . ?
C9 N1 C21 124.0(4) . . ?
O6 N2 O5 123.7(6) . . ?
O6 N2 C13 117.1(5) . . ?
O5 N2 C13 119.0(5) . . ?
C6 C1 C2 122.8(6) . . ?
C6 C1 Br1 119.4(4) . . ?
C2 C1 Br1 117.7(4) . . ?
C3 C2 C1 116.8(5) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 122.8(5) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 117.6(5) . . ?
C3 C4 C7 118.6(5) . . ?
C5 C4 C7 123.7(5) . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 118.6(5) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C4 130.5(5) . . ?
C8 C7 H7 114.7 . . ?
C4 C7 H7 114.7 . . ?
C7 C8 C9 119.0(5) . . ?
C7 C8 C11 132.7(5) . . ?
C9 C8 C11 108.2(4) . . ?
O1 C9 N1 122.9(5) . . ?
O1 C9 C8 130.0(5) . . ?
N1 C9 C8 107.1(4) . . ?
O2 C10 N1 124.2(5) . . ?
O2 C10 C11 128.6(5) . . ?
N1 C10 C11 107.2(4) . . ?
C8 C11 C10 103.8(4) . . ?
C8 C11 C12 112.4(4) . . ?
C10 C11 C12 112.9(4) . . ?
C8 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C14 C12 C13 112.1(4) . . ?
C14 C12 C11 113.0(4) . . ?
C13 C12 C11 110.9(4) . . ?
C14 C12 H12 106.8 . . ?
C13 C12 H12 106.8 . . ?
C11 C12 H12 106.8 . . ?
N2 C13 C12 110.6(4) . . ?
N2 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C19 117.4(5) . . ?
C15 C14 C12 123.6(4) . . ?
C19 C14 C12 119.0(4) . . ?
C14 C15 C16 122.2(5) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C17 119.3(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
O7 C17 C18 115.7(5) . . ?
O7 C17 C16 124.9(5) . . ?
C18 C17 C16 119.4(5) . . ?
C19 C18 C17 120.0(5) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.7(5) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 O4 128.4(5) . . ?
O3 C21 N1 122.1(5) . . ?
O4 C21 N1 109.5(4) . . ?
O4 C22 C24 107.6(5) . . ?
O4 C22 C23 109.8(5) . . ?
C24 C22 C23 114.2(6) . . ?
O4 C22 C25 102.6(5) . . ?
C24 C22 C25 111.5(6) . . ?
C23 C22 C25 110.6(6) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C46 O11 C47 119.9(4) . . ?
C42 O14 C45 117.1(5) . . ?
C35 N3 C34 113.1(4) . . ?
C35 N3 C46 122.7(4) . . ?
C34 N3 C46 123.7(4) . . ?
O12 N4 O13 123.7(5) . . ?
O12 N4 C38 117.7(4) . . ?
O13 N4 C38 118.6(5) . . ?
C31 C26 C27 121.0(5) . . ?
C31 C26 Br2 118.5(4) . . ?
C27 C26 Br2 120.5(4) . . ?
C28 C27 C26 118.8(5) . . ?
C28 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
C27 C28 C29 122.4(5) . . ?
C27 C28 H28 118.8 . . ?
C29 C28 H28 118.8 . . ?
C30 C29 C28 117.5(5) . . ?
C30 C29 C32 124.5(5) . . ?
C28 C29 C32 118.0(4) . . ?
C31 C30 C29 121.0(5) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C26 C31 C30 119.3(5) . . ?
C26 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C33 C32 C29 129.5(5) . . ?
C33 C32 H32 115.2 . . ?
C29 C32 H32 115.2 . . ?
C32 C33 C34 120.0(5) . . ?
C32 C33 C36 131.8(5) . . ?
C34 C33 C36 108.1(4) . . ?
O9 C34 N3 124.1(5) . . ?
O9 C34 C33 129.3(5) . . ?
N3 C34 C33 106.6(4) . . ?
O8 C35 N3 125.1(5) . . ?
O8 C35 C36 126.7(5) . . ?
N3 C35 C36 108.1(4) . . ?
C33 C36 C35 103.4(4) . . ?
C33 C36 C37 110.5(4) . . ?
C35 C36 C37 111.6(4) . . ?
C33 C36 H36 110.4 . . ?
C35 C36 H36 110.4 . . ?
C37 C36 H36 110.4 . . ?
C39 C37 C38 112.8(4) . . ?
C39 C37 C36 113.9(4) . . ?
C38 C37 C36 110.0(4) . . ?
C39 C37 H37 106.5 . . ?
C38 C37 H37 106.5 . . ?
C36 C37 H37 106.5 . . ?
N4 C38 C37 109.3(4) . . ?
N4 C38 H38A 109.8 . . ?
C37 C38 H38A 109.8 . . ?
N4 C38 H38B 109.8 . . ?
C37 C38 H38B 109.8 . . ?
H38A C38 H38B 108.3 . . ?
C40 C39 C44 117.5(5) . . ?
C40 C39 C37 122.5(4) . . ?
C44 C39 C37 120.0(5) . . ?
C39 C40 C41 121.7(5) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C42 C41 C40 120.3(5) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
O14 C42 C41 125.1(5) . . ?
O14 C42 C43 116.1(5) . . ?
C41 C42 C43 118.8(5) . . ?
C44 C43 C42 120.6(5) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C39 121.1(5) . . ?
C43 C44 H44 119.4 . . ?
C39 C44 H44 119.4 . . ?
O14 C45 H45A 109.5 . . ?
O14 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O14 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O10 C46 O11 129.8(5) . . ?
O10 C46 N3 121.3(5) . . ?
O11 C46 N3 108.9(4) . . ?
C48 C47 O11 109.8(5) . . ?
C48 C47 C50 113.8(5) . . ?
O11 C47 C50 108.6(4) . . ?
C48 C47 C49 110.3(5) . . ?
O11 C47 C49 101.7(4) . . ?
C50 C47 C49 111.8(5) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
C6 C1 C2 C3 -0.7(10) . . . . ?
Br1 C1 C2 C3 178.1(5) . . . . ?
C1 C2 C3 C4 2.2(9) . . . . ?
C2 C3 C4 C5 -2.3(9) . . . . ?
C2 C3 C4 C7 -179.8(6) . . . . ?
C3 C4 C5 C6 0.9(9) . . . . ?
C7 C4 C5 C6 178.3(5) . . . . ?
C2 C1 C6 C5 -0.6(10) . . . . ?
Br1 C1 C6 C5 -179.4(5) . . . . ?
C4 C5 C6 C1 0.5(9) . . . . ?
C3 C4 C7 C8 -157.3(6) . . . . ?
C5 C4 C7 C8 25.3(9) . . . . ?
C4 C7 C8 C9 -178.0(5) . . . . ?
C4 C7 C8 C11 5.7(10) . . . . ?
C10 N1 C9 O1 -176.0(6) . . . . ?
C21 N1 C9 O1 3.5(9) . . . . ?
C10 N1 C9 C8 5.0(6) . . . . ?
C21 N1 C9 C8 -175.5(5) . . . . ?
C7 C8 C9 O1 -4.1(10) . . . . ?
C11 C8 C9 O1 173.0(6) . . . . ?
C7 C8 C9 N1 174.8(5) . . . . ?
C11 C8 C9 N1 -8.1(6) . . . . ?
C9 N1 C10 O2 -179.9(5) . . . . ?
C21 N1 C10 O2 0.6(8) . . . . ?
C9 N1 C10 C11 0.1(6) . . . . ?
C21 N1 C10 C11 -179.4(4) . . . . ?
C7 C8 C11 C10 -175.6(5) . . . . ?
C9 C8 C11 C10 7.9(5) . . . . ?
C7 C8 C11 C12 62.0(7) . . . . ?
C9 C8 C11 C12 -114.5(5) . . . . ?
O2 C10 C11 C8 175.0(5) . . . . ?
N1 C10 C11 C8 -5.0(5) . . . . ?
O2 C10 C11 C12 -62.9(7) . . . . ?
N1 C10 C11 C12 117.1(4) . . . . ?
C8 C11 C12 C14 37.4(6) . . . . ?
C10 C11 C12 C14 -79.7(5) . . . . ?
C8 C11 C12 C13 164.2(4) . . . . ?
C10 C11 C12 C13 47.1(5) . . . . ?
O6 N2 C13 C12 138.1(5) . . . . ?
O5 N2 C13 C12 -44.6(7) . . . . ?
C14 C12 C13 N2 -62.7(6) . . . . ?
C11 C12 C13 N2 170.0(4) . . . . ?
C13 C12 C14 C15 -47.3(7) . . . . ?
C11 C12 C14 C15 79.0(6) . . . . ?
C13 C12 C14 C19 132.5(5) . . . . ?
C11 C12 C14 C19 -101.3(5) . . . . ?
C19 C14 C15 C16 -0.6(8) . . . . ?
C12 C14 C15 C16 179.2(5) . . . . ?
C14 C15 C16 C17 -1.0(8) . . . . ?
C20 O7 C17 C18 -166.0(5) . . . . ?
C20 O7 C17 C16 13.4(8) . . . . ?
C15 C16 C17 O7 -177.3(5) . . . . ?
C15 C16 C17 C18 2.1(8) . . . . ?
O7 C17 C18 C19 177.9(5) . . . . ?
C16 C17 C18 C19 -1.5(8) . . . . ?
C17 C18 C19 C14 -0.1(8) . . . . ?
C15 C14 C19 C18 1.2(8) . . . . ?
C12 C14 C19 C18 -178.6(5) . . . . ?
C22 O4 C21 O3 -10.9(10) . . . . ?
C22 O4 C21 N1 170.3(5) . . . . ?
C10 N1 C21 O3 117.2(6) . . . . ?
C9 N1 C21 O3 -62.2(8) . . . . ?
C10 N1 C21 O4 -63.8(7) . . . . ?
C9 N1 C21 O4 116.8(6) . . . . ?
C21 O4 C22 C24 -61.4(7) . . . . ?
C21 O4 C22 C23 63.4(7) . . . . ?
C21 O4 C22 C25 -179.1(5) . . . . ?
C31 C26 C27 C28 0.3(9) . . . . ?
Br2 C26 C27 C28 -178.8(4) . . . . ?
C26 C27 C28 C29 1.5(9) . . . . ?
C27 C28 C29 C30 -2.3(8) . . . . ?
C27 C28 C29 C32 179.1(5) . . . . ?
C28 C29 C30 C31 1.2(8) . . . . ?
C32 C29 C30 C31 179.7(5) . . . . ?
C27 C26 C31 C30 -1.3(9) . . . . ?
Br2 C26 C31 C30 177.8(4) . . . . ?
C29 C30 C31 C26 0.5(8) . . . . ?
C30 C29 C32 C33 22.2(9) . . . . ?
C28 C29 C32 C33 -159.3(5) . . . . ?
C29 C32 C33 C34 179.7(5) . . . . ?
C29 C32 C33 C36 4.3(9) . . . . ?
C35 N3 C34 O9 -173.5(5) . . . . ?
C46 N3 C34 O9 -0.6(8) . . . . ?
C35 N3 C34 C33 4.5(6) . . . . ?
C46 N3 C34 C33 177.5(4) . . . . ?
C32 C33 C34 O9 -6.7(9) . . . . ?
C36 C33 C34 O9 169.8(6) . . . . ?
C32 C33 C34 N3 175.4(4) . . . . ?
C36 C33 C34 N3 -8.2(5) . . . . ?
C34 N3 C35 O8 177.7(5) . . . . ?
C46 N3 C35 O8 4.7(8) . . . . ?
C34 N3 C35 C36 1.0(6) . . . . ?
C46 N3 C35 C36 -172.0(4) . . . . ?
C32 C33 C36 C35 -175.7(5) . . . . ?
C34 C33 C36 C35 8.5(5) . . . . ?
C32 C33 C36 C37 64.7(7) . . . . ?
C34 C33 C36 C37 -111.2(5) . . . . ?
O8 C35 C36 C33 177.5(5) . . . . ?
N3 C35 C36 C33 -5.8(5) . . . . ?
O8 C35 C36 C37 -63.6(6) . . . . ?
N3 C35 C36 C37 113.0(5) . . . . ?
C33 C36 C37 C39 48.0(6) . . . . ?
C35 C36 C37 C39 -66.5(5) . . . . ?
C33 C36 C37 C38 175.8(4) . . . . ?
C35 C36 C37 C38 61.3(5) . . . . ?
O12 N4 C38 C37 132.9(5) . . . . ?
O13 N4 C38 C37 -49.7(6) . . . . ?
C39 C37 C38 N4 -56.9(6) . . . . ?
C36 C37 C38 N4 174.7(4) . . . . ?
C38 C37 C39 C40 -50.5(7) . . . . ?
C36 C37 C39 C40 75.8(6) . . . . ?
C38 C37 C39 C44 127.6(5) . . . . ?
C36 C37 C39 C44 -106.1(5) . . . . ?
C44 C39 C40 C41 0.5(8) . . . . ?
C37 C39 C40 C41 178.6(5) . . . . ?
C39 C40 C41 C42 -1.4(9) . . . . ?
C45 O14 C42 C41 3.2(8) . . . . ?
C45 O14 C42 C43 -175.8(5) . . . . ?
C40 C41 C42 O14 -177.6(5) . . . . ?
C40 C41 C42 C43 1.4(8) . . . . ?
O14 C42 C43 C44 178.5(5) . . . . ?
C41 C42 C43 C44 -0.6(9) . . . . ?
C42 C43 C44 C39 -0.3(9) . . . . ?
C40 C39 C44 C43 0.3(8) . . . . ?
C37 C39 C44 C43 -177.9(5) . . . . ?
C47 O11 C46 O10 -9.5(10) . . . . ?
C47 O11 C46 N3 170.5(4) . . . . ?
C35 N3 C46 O10 115.6(7) . . . . ?
C34 N3 C46 O10 -56.6(8) . . . . ?
C35 N3 C46 O11 -64.3(6) . . . . ?
C34 N3 C46 O11 123.4(5) . . . . ?
C46 O11 C47 C48 63.2(7) . . . . ?
C46 O11 C47 C50 -61.9(6) . . . . ?
C46 O11 C47 C49 180.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.67
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.105
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'Ethyl acetate/Petroleum ether'
