# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1021346'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br N3 O5'
_chemical_formula_weight         514.37

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.8260(9)
_cell_length_b                   16.2679(17)
_cell_length_c                   16.3883(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2353.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    1.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5002
_exptl_absorpt_correction_T_max  0.7880
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27004
_diffrn_reflns_av_R_equivalents  0.1385
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4152
_reflns_number_gt                3091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0687P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0070(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4152
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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 0.18005(7) 0.22335(3) 0.04179(3) 0.0517(2) Uani 1 1 d . . .
O2 O -0.2944(4) 0.0824(2) -0.0901(2) 0.0470(9) Uani 1 1 d . . .
O5 O -0.0123(4) -0.2174(3) -0.0795(2) 0.0458(9) Uani 1 1 d . . .
O1 O -0.1115(4) 0.0755(2) -0.18349(19) 0.0406(9) Uani 1 1 d . . .
O4 O 0.0380(4) -0.1057(2) 0.09667(19) 0.0416(9) Uani 1 1 d . . .
O3 O -0.1997(5) -0.1115(2) 0.14935(19) 0.0511(11) Uani 1 1 d . . .
N1 N 0.1825(5) -0.1225(3) -0.0861(2) 0.0370(9) Uani 1 1 d . . .
N2 N -0.1580(5) -0.0861(3) 0.0149(2) 0.0352(10) Uani 1 1 d . . .
N3 N -0.3267(5) -0.0833(3) -0.0882(2) 0.0381(10) Uani 1 1 d . . .
C1 C -0.2697(6) -0.1254(3) -0.2509(3) 0.0432(14) Uani 1 1 d . . .
H1A H -0.3666 -0.1327 -0.2268 0.052 Uiso 1 1 calc R . .
C2 C -0.2426(8) -0.1524(4) -0.3299(3) 0.0575(18) Uani 1 1 d . . .
H2A H -0.3223 -0.1778 -0.3596 0.069 Uiso 1 1 calc R . .
C3 C -0.1053(8) -0.1434(4) -0.3656(3) 0.066(2) Uani 1 1 d . . .
H3A H -0.0886 -0.1629 -0.4195 0.079 Uiso 1 1 calc R . .
C4 C 0.0107(7) -0.1056(4) -0.3228(3) 0.0530(16) Uani 1 1 d . . .
H4A H 0.1073 -0.0987 -0.3474 0.064 Uiso 1 1 calc R . .
C5 C -0.0139(6) -0.0781(4) -0.2452(3) 0.0443(14) Uani 1 1 d . . .
H5A H 0.0665 -0.0520 -0.2166 0.053 Uiso 1 1 calc R . .
C6 C -0.1531(6) -0.0871(3) -0.2069(3) 0.0346(12) Uani 1 1 d . . .
C7 C -0.1851(6) -0.0508(3) -0.1232(2) 0.0338(11) Uani 1 1 d . . .
C8 C -0.3064(6) -0.0978(3) -0.0140(3) 0.0417(13) Uani 1 1 d . . .
H8A H -0.3863 -0.1155 0.0207 0.050 Uiso 1 1 calc R . .
C9 C -0.0592(5) -0.0698(3) -0.0550(3) 0.0288(11) Uani 1 1 d . . .
C10 C -0.1132(6) -0.1020(3) 0.0936(3) 0.0418(14) Uani 1 1 d . . .
C11 C 0.0610(5) -0.0058(3) -0.0429(3) 0.0317(11) Uani 1 1 d . . .
C12 C 0.0521(6) 0.0723(3) -0.0113(3) 0.0350(12) Uani 1 1 d . . .
H12A H -0.0419 0.0945 0.0064 0.042 Uiso 1 1 calc R . .
C13 C 0.1855(7) 0.1180(3) -0.0059(3) 0.0403(12) Uani 1 1 d . . .
C14 C 0.3229(6) 0.0855(3) -0.0330(3) 0.0399(12) Uani 1 1 d . . .
H14A H 0.4116 0.1185 -0.0316 0.048 Uiso 1 1 calc R . .
C15 C 0.3312(6) 0.0061(4) -0.0620(3) 0.0404(13) Uani 1 1 d . . .
H15A H 0.4248 -0.0167 -0.0796 0.049 Uiso 1 1 calc R . .
C16 C 0.1983(6) -0.0395(3) -0.0646(2) 0.0346(12) Uani 1 1 d . . .
C17 C 0.0344(6) -0.1482(4) -0.0745(3) 0.0379(13) Uani 1 1 d . . .
C18 C 0.3039(7) -0.1784(4) -0.1064(4) 0.0574(16) Uani 1 1 d . . .
H18A H 0.3988 -0.1476 -0.1117 0.086 Uiso 1 1 calc R . .
H18B H 0.2808 -0.2059 -0.1581 0.086 Uiso 1 1 calc R . .
H18C H 0.3143 -0.2195 -0.0631 0.086 Uiso 1 1 calc R . .
C19 C -0.2055(6) 0.0435(3) -0.1302(3) 0.0330(12) Uani 1 1 d . . .
C20 C -0.1106(7) 0.1644(4) -0.1917(3) 0.0476(14) Uani 1 1 d . . .
H20A H -0.0371 0.1804 -0.2336 0.071 Uiso 1 1 calc R . .
H20B H -0.0825 0.1894 -0.1394 0.071 Uiso 1 1 calc R . .
H20C H -0.2118 0.1833 -0.2076 0.071 Uiso 1 1 calc R . .
C21 C 0.1215(6) -0.1005(4) 0.1746(3) 0.0465(15) Uani 1 1 d . . .
C22 C 0.2842(7) -0.1012(5) 0.1469(4) 0.0646(19) Uani 1 1 d . . .
H22A H 0.3031 -0.0535 0.1119 0.097 Uiso 1 1 calc R . .
H22C H 0.3044 -0.1517 0.1163 0.097 Uiso 1 1 calc R . .
H22D H 0.3510 -0.0988 0.1946 0.097 Uiso 1 1 calc R . .
C23 C 0.0851(10) -0.1726(5) 0.2287(5) 0.090(3) Uani 1 1 d . . .
H23B H -0.0215 -0.1699 0.2453 0.135 Uiso 1 1 calc R . .
H23C H 0.1498 -0.1710 0.2772 0.135 Uiso 1 1 calc R . .
H23A H 0.1031 -0.2238 0.1988 0.135 Uiso 1 1 calc R . .
C24 C 0.0833(7) -0.0186(4) 0.2133(3) 0.0618(18) Uani 1 1 d . . .
H24B H -0.0230 -0.0187 0.2306 0.093 Uiso 1 1 calc R . .
H24C H 0.0994 0.0255 0.1735 0.093 Uiso 1 1 calc R . .
H24D H 0.1486 -0.0095 0.2608 0.093 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 C13 1.885(5) . ?
O2 C19 1.204(5) . ?
O5 C17 1.201(6) . ?
O1 C19 1.312(6) . ?
O1 C20 1.452(6) . ?
O4 C10 1.338(6) . ?
O4 C21 1.476(6) . ?
O3 C10 1.200(6) . ?
N1 C17 1.386(7) . ?
N1 C16 1.402(6) . ?
N1 C18 1.443(7) . ?
N2 C10 1.374(6) . ?
N2 C8 1.406(7) . ?
N2 C9 1.463(6) . ?
N3 C8 1.251(6) . ?
N3 C7 1.473(6) . ?
C1 C2 1.388(7) . ?
C1 C6 1.402(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.354(9) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.366(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.387(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.520(6) . ?
C7 C19 1.549(7) . ?
C7 C9 1.607(6) . ?
C8 H8A 0.9500 . ?
C9 C11 1.499(7) . ?
C9 C17 1.553(7) . ?
C11 C12 1.375(7) . ?
C11 C16 1.376(7) . ?
C12 C13 1.395(8) . ?
C12 H12A 0.9500 . ?
C13 C14 1.394(8) . ?
C14 C15 1.379(8) . ?
C14 H14A 0.9500 . ?
C15 C16 1.389(7) . ?
C15 H15A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.505(8) . ?
C21 C22 1.506(8) . ?
C21 C24 1.515(8) . ?
C22 H22A 0.9800 . ?
C22 H22C 0.9800 . ?
C22 H22D 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 H24D 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
C19 O1 C20 117.4(4) . . ?
C10 O4 C21 121.9(4) . . ?
C17 N1 C16 110.5(4) . . ?
C17 N1 C18 122.8(4) . . ?
C16 N1 C18 126.2(5) . . ?
C10 N2 C8 123.9(4) . . ?
C10 N2 C9 126.7(4) . . ?
C8 N2 C9 108.5(4) . . ?
C8 N3 C7 108.9(4) . . ?
C2 C1 C6 119.6(5) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C3 C2 C1 121.6(6) . . ?
C3 C2 H2A 119.2 . . ?
C1 C2 H2A 119.2 . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 121.8(5) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C1 117.7(4) . . ?
C5 C6 C7 122.1(5) . . ?
C1 C6 C7 120.0(5) . . ?
N3 C7 C6 111.7(4) . . ?
N3 C7 C19 106.7(4) . . ?
C6 C7 C19 109.9(4) . . ?
N3 C7 C9 104.3(3) . . ?
C6 C7 C9 115.1(4) . . ?
C19 C7 C9 108.8(4) . . ?
N3 C8 N2 115.8(5) . . ?
N3 C8 H8A 122.1 . . ?
N2 C8 H8A 122.1 . . ?
N2 C9 C11 116.4(4) . . ?
N2 C9 C17 109.3(4) . . ?
C11 C9 C17 102.8(4) . . ?
N2 C9 C7 99.6(3) . . ?
C11 C9 C7 116.6(4) . . ?
C17 C9 C7 112.5(4) . . ?
O3 C10 O4 126.9(5) . . ?
O3 C10 N2 123.8(5) . . ?
O4 C10 N2 109.3(4) . . ?
C12 C11 C16 121.1(5) . . ?
C12 C11 C9 130.6(4) . . ?
C16 C11 C9 108.2(4) . . ?
C11 C12 C13 117.9(5) . . ?
C11 C12 H12A 121.1 . . ?
C13 C12 H12A 121.1 . . ?
C14 C13 C12 120.8(5) . . ?
C14 C13 Br1 119.9(4) . . ?
C12 C13 Br1 119.2(4) . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 117.8(5) . . ?
C14 C15 H15A 121.1 . . ?
C16 C15 H15A 121.1 . . ?
C11 C16 C15 121.5(5) . . ?
C11 C16 N1 111.2(5) . . ?
C15 C16 N1 127.3(5) . . ?
O5 C17 N1 126.7(5) . . ?
O5 C17 C9 126.9(5) . . ?
N1 C17 C9 106.4(4) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 O1 124.5(5) . . ?
O2 C19 C7 123.8(5) . . ?
O1 C19 C7 111.7(4) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C23 111.0(5) . . ?
O4 C21 C22 102.4(4) . . ?
C23 C21 C22 112.1(6) . . ?
O4 C21 C24 107.5(4) . . ?
C23 C21 C24 113.1(5) . . ?
C22 C21 C24 110.2(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
C21 C22 H22D 109.5 . . ?
H22A C22 H22D 109.5 . . ?
H22C C22 H22D 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
H23B C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C24 H24D 109.5 . . ?
H24B C24 H24D 109.5 . . ?
H24C C24 H24D 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 0.6(10) . . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
C2 C3 C4 C5 0.3(10) . . . . ?
C3 C4 C5 C6 0.3(10) . . . . ?
C4 C5 C6 C1 -0.4(9) . . . . ?
C4 C5 C6 C7 -175.1(5) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
C2 C1 C6 C7 174.8(5) . . . . ?
C8 N3 C7 C6 138.4(5) . . . . ?
C8 N3 C7 C19 -101.6(5) . . . . ?
C8 N3 C7 C9 13.5(5) . . . . ?
C5 C6 C7 N3 -167.7(5) . . . . ?
C1 C6 C7 N3 17.8(7) . . . . ?
C5 C6 C7 C19 74.2(7) . . . . ?
C1 C6 C7 C19 -100.3(6) . . . . ?
C5 C6 C7 C9 -49.0(7) . . . . ?
C1 C6 C7 C9 136.4(5) . . . . ?
C7 N3 C8 N2 -4.6(7) . . . . ?
C10 N2 C8 N3 -177.3(5) . . . . ?
C9 N2 C8 N3 -7.6(7) . . . . ?
C10 N2 C9 C11 -50.1(7) . . . . ?
C8 N2 C9 C11 140.6(4) . . . . ?
C10 N2 C9 C17 65.7(6) . . . . ?
C8 N2 C9 C17 -103.6(5) . . . . ?
C10 N2 C9 C7 -176.2(5) . . . . ?
C8 N2 C9 C7 14.5(5) . . . . ?
N3 C7 C9 N2 -16.5(4) . . . . ?
C6 C7 C9 N2 -139.2(4) . . . . ?
C19 C7 C9 N2 97.0(4) . . . . ?
N3 C7 C9 C11 -142.5(4) . . . . ?
C6 C7 C9 C11 94.8(5) . . . . ?
C19 C7 C9 C11 -29.0(5) . . . . ?
N3 C7 C9 C17 99.1(5) . . . . ?
C6 C7 C9 C17 -23.6(6) . . . . ?
C19 C7 C9 C17 -147.4(4) . . . . ?
C21 O4 C10 O3 -16.8(9) . . . . ?
C21 O4 C10 N2 163.9(5) . . . . ?
C8 N2 C10 O3 -15.5(9) . . . . ?
C9 N2 C10 O3 176.8(5) . . . . ?
C8 N2 C10 O4 163.9(5) . . . . ?
C9 N2 C10 O4 -3.9(7) . . . . ?
N2 C9 C11 C12 -48.4(7) . . . . ?
C17 C9 C11 C12 -167.7(5) . . . . ?
C7 C9 C11 C12 68.7(7) . . . . ?
N2 C9 C11 C16 127.3(4) . . . . ?
C17 C9 C11 C16 8.0(5) . . . . ?
C7 C9 C11 C16 -115.6(4) . . . . ?
C16 C11 C12 C13 3.4(7) . . . . ?
C9 C11 C12 C13 178.6(5) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C11 C12 C13 Br1 -177.0(3) . . . . ?
C12 C13 C14 C15 -3.3(7) . . . . ?
Br1 C13 C14 C15 174.7(3) . . . . ?
C13 C14 C15 C16 1.2(7) . . . . ?
C12 C11 C16 C15 -5.5(7) . . . . ?
C9 C11 C16 C15 178.3(4) . . . . ?
C12 C11 C16 N1 172.9(4) . . . . ?
C9 C11 C16 N1 -3.3(5) . . . . ?
C14 C15 C16 C11 3.1(7) . . . . ?
C14 C15 C16 N1 -175.1(4) . . . . ?
C17 N1 C16 C11 -3.7(5) . . . . ?
C18 N1 C16 C11 -175.4(5) . . . . ?
C17 N1 C16 C15 174.7(4) . . . . ?
C18 N1 C16 C15 3.0(8) . . . . ?
C16 N1 C17 O5 -172.1(5) . . . . ?
C18 N1 C17 O5 -0.1(8) . . . . ?
C16 N1 C17 C9 8.6(5) . . . . ?
C18 N1 C17 C9 -179.3(4) . . . . ?
N2 C9 C17 O5 46.6(6) . . . . ?
C11 C9 C17 O5 170.8(5) . . . . ?
C7 C9 C17 O5 -63.0(6) . . . . ?
N2 C9 C17 N1 -134.2(4) . . . . ?
C11 C9 C17 N1 -10.0(5) . . . . ?
C7 C9 C17 N1 116.2(4) . . . . ?
C20 O1 C19 O2 2.8(7) . . . . ?
C20 O1 C19 C7 -175.5(4) . . . . ?
N3 C7 C19 O2 22.5(6) . . . . ?
C6 C7 C19 O2 143.7(4) . . . . ?
C9 C7 C19 O2 -89.5(6) . . . . ?
N3 C7 C19 O1 -159.2(3) . . . . ?
C6 C7 C19 O1 -38.0(6) . . . . ?
C9 C7 C19 O1 88.8(4) . . . . ?
C10 O4 C21 C23 64.2(7) . . . . ?
C10 O4 C21 C22 -176.0(5) . . . . ?
C10 O4 C21 C24 -59.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1047214'
_audit_update_record             
;
2015-02-04 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(R)-Methyl 2-((R)-5-bromo-3-((tert-butoxycarbonyl)amino)-1-methyl-2-oxoindolin-3-yl)-2- isocyano-2-phenylacetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H26 Br Cl2 N3 O5'
_chemical_formula_weight         599.30

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.5000(10)
_cell_length_b                   14.8773(16)
_cell_length_c                   19.875(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2809.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4973
_exptl_absorpt_correction_T_max  0.6674
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32871
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4948
_reflns_number_gt                4137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1196P)²+1.4879P] 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
_chemical_absolute_configuration ad
_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   0.016(13)
_refine_ls_number_reflns         4948
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1774
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -1.00547(6) -0.18349(4) 0.33581(3) 0.0685(2) Uani 1 1 d . . .
N1 N -0.6094(5) 0.1199(3) 0.4151(2) 0.0565(11) Uani 1 1 d . . .
N2 N -0.7148(5) 0.1471(3) 0.23830(19) 0.0477(9) Uani 1 1 d . . .
H2B H -0.7717 0.1914 0.2437 0.057 Uiso 1 1 calc R . .
N3 N -0.4532(5) 0.0096(3) 0.3026(2) 0.0545(11) Uani 1 1 d . . .
C1 C -0.8428(6) 0.1675(4) 0.3789(2) 0.0500(12) Uani 1 1 d . . .
C2 C -0.8939(7) 0.1174(5) 0.4308(3) 0.0707(16) Uani 1 1 d . . .
H2A H -0.8319 0.0839 0.4569 0.085 Uiso 1 1 calc R . .
C3 C -1.0392(8) 0.1152(6) 0.4459(4) 0.091(2) Uani 1 1 d . . .
H3A H -1.0728 0.0807 0.4815 0.110 Uiso 1 1 calc R . .
C4 C -1.1287(8) 0.1641(7) 0.4075(4) 0.094(2) Uani 1 1 d . . .
H4A H -1.2244 0.1656 0.4174 0.113 Uiso 1 1 calc R . .
C5 C -1.0768(7) 0.2105(6) 0.3549(4) 0.084(2) Uani 1 1 d . . .
H5A H -1.1402 0.2398 0.3267 0.101 Uiso 1 1 calc R . .
C6 C -0.9326(7) 0.2174(5) 0.3400(4) 0.0731(17) Uani 1 1 d . . .
H6A H -0.8998 0.2541 0.3055 0.088 Uiso 1 1 calc R . .
C7 C -0.4904(6) 0.0968(3) 0.2892(2) 0.0495(11) Uani 1 1 d . . .
C8 C -0.6538(5) 0.1029(3) 0.2964(2) 0.0441(11) Uani 1 1 d . . .
C9 C -0.6965(5) 0.0071(3) 0.3070(2) 0.0464(11) Uani 1 1 d . . .
C10 C -0.8245(5) -0.0330(3) 0.3135(2) 0.0464(11) Uani 1 1 d . . .
H10A H -0.9072 0.0003 0.3108 0.056 Uiso 1 1 calc R . .
C11 C -0.8276(6) -0.1253(3) 0.3244(2) 0.0504(12) Uani 1 1 d . . .
C12 C -0.7085(6) -0.1773(3) 0.3268(3) 0.0535(12) Uani 1 1 d . . .
H12A H -0.7154 -0.2392 0.3328 0.064 Uiso 1 1 calc R . .
C13 C -0.5753(6) -0.1360(3) 0.3202(3) 0.0551(13) Uani 1 1 d . . .
H13A H -0.4927 -0.1696 0.3217 0.066 Uiso 1 1 calc R . .
C14 C -0.5722(5) -0.0450(3) 0.3115(2) 0.0454(11) Uani 1 1 d . . .
C15 C -0.3110(6) -0.0200(4) 0.3044(4) 0.0662(16) Uani 1 1 d . . .
H15A H -0.2495 0.0304 0.2976 0.099 Uiso 1 1 calc R . .
H15B H -0.2958 -0.0635 0.2695 0.099 Uiso 1 1 calc R . .
H15C H -0.2917 -0.0468 0.3474 0.099 Uiso 1 1 calc R . .
C16 C -0.6817(5) 0.1182(3) 0.1748(2) 0.0477(11) Uani 1 1 d . . .
C17 C -0.6824(6) 0.1692(4) 0.0579(2) 0.0571(13) Uani 1 1 d . . .
C18 C -0.5367(9) 0.1385(7) 0.0459(4) 0.104(3) Uani 1 1 d . . .
H18A H -0.4719 0.1810 0.0649 0.156 Uiso 1 1 calc R . .
H18B H -0.5204 0.1337 -0.0016 0.156 Uiso 1 1 calc R . .
H18C H -0.5230 0.0809 0.0666 0.156 Uiso 1 1 calc R . .
C19 C -0.7946(10) 0.1086(7) 0.0316(4) 0.106(3) Uani 1 1 d . . .
H19A H -0.7815 0.0999 -0.0159 0.160 Uiso 1 1 calc R . .
H19B H -0.8852 0.1353 0.0395 0.160 Uiso 1 1 calc R . .
H19C H -0.7896 0.0516 0.0542 0.160 Uiso 1 1 calc R . .
C20 C -0.6999(11) 0.2643(6) 0.0305(3) 0.097(3) Uani 1 1 d . . .
H20A H -0.6279 0.3024 0.0489 0.146 Uiso 1 1 calc R . .
H20B H -0.7907 0.2872 0.0431 0.146 Uiso 1 1 calc R . .
H20C H -0.6921 0.2633 -0.0176 0.146 Uiso 1 1 calc R . .
C21 C -0.6859(5) 0.1625(3) 0.3613(2) 0.0457(11) Uani 1 1 d . . .
C22 C -0.6227(6) 0.2582(3) 0.3500(3) 0.0516(12) Uani 1 1 d . . .
C23 C -0.4429(9) 0.3597(4) 0.3764(4) 0.083(2) Uani 1 1 d . . .
H23A H -0.3667 0.3674 0.4076 0.124 Uiso 1 1 calc R . .
H23B H -0.5075 0.4090 0.3808 0.124 Uiso 1 1 calc R . .
H23C H -0.4065 0.3580 0.3314 0.124 Uiso 1 1 calc R . .
C24 C -0.5423(9) 0.0860(5) 0.4569(4) 0.090(2) Uani 1 1 d . . .
O1 O -0.6678(4) 0.3081(2) 0.3078(2) 0.0633(10) Uani 1 1 d . . .
O2 O -0.5153(5) 0.2763(3) 0.3909(2) 0.0678(10) Uani 1 1 d . . .
O3 O -0.6372(5) 0.0454(3) 0.1636(2) 0.0729(12) Uani 1 1 d . . .
O4 O -0.7051(4) 0.1831(2) 0.13130(16) 0.0535(8) Uani 1 1 d . . .
O5 O -0.4135(4) 0.1591(3) 0.2768(2) 0.0658(10) Uani 1 1 d . . .
Cl1 Cl -0.7748(6) 0.5332(5) 0.4111(6) 0.354(6) Uani 1 1 d . . .
Cl2 Cl -0.9942(7) 0.5032(8) 0.3291(2) 0.408(8) Uani 1 1 d . . .
C01 C -0.892(3) 0.4600(7) 0.3836(11) 0.286(16) Uani 1 1 d . . .
H01B H -0.8434 0.4091 0.3638 0.344 Uiso 1 1 calc R . .
H01A H -0.9471 0.4382 0.4212 0.344 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 C11 1.912(5) . ?
N1 C24 1.161(8) . ?
N1 C21 1.440(7) . ?
N2 C16 1.370(6) . ?
N2 C8 1.448(6) . ?
N2 H2B 0.8600 . ?
N3 C7 1.371(6) . ?
N3 C14 1.403(7) . ?
N3 C15 1.421(7) . ?
C1 C2 1.362(8) . ?
C1 C6 1.370(8) . ?
C1 C21 1.532(7) . ?
C2 C3 1.413(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.353(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.348(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.405(10) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 O5 1.205(6) . ?
C7 C8 1.562(8) . ?
C8 C9 1.496(7) . ?
C8 C21 1.595(7) . ?
C9 C10 1.361(7) . ?
C9 C14 1.415(7) . ?
C10 C11 1.390(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.372(8) . ?
C12 C13 1.413(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.366(7) . ?
C13 H13A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.183(6) . ?
C16 O4 1.315(6) . ?
C17 C18 1.477(10) . ?
C17 O4 1.488(6) . ?
C17 C19 1.491(10) . ?
C17 C20 1.526(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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 1.562(7) . ?
C22 O1 1.200(6) . ?
C22 O2 1.331(7) . ?
C23 O2 1.447(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
Cl1 C01 1.65(2) . ?
Cl2 C01 1.59(3) . ?
C01 H01B 0.9700 . ?
C01 H01A 0.9700 . ?

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
C24 N1 C21 177.0(7) . . ?
C16 N2 C8 120.0(4) . . ?
C16 N2 H2B 120.0 . . ?
C8 N2 H2B 120.0 . . ?
C7 N3 C14 111.3(4) . . ?
C7 N3 C15 122.9(5) . . ?
C14 N3 C15 125.7(5) . . ?
C2 C1 C6 120.1(6) . . ?
C2 C1 C21 119.5(5) . . ?
C6 C1 C21 120.3(5) . . ?
C1 C2 C3 121.5(7) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 118.8(7) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C5 C4 C3 118.9(7) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 123.9(7) . . ?
C4 C5 H5A 118.1 . . ?
C6 C5 H5A 118.1 . . ?
C1 C6 C5 116.7(6) . . ?
C1 C6 H6A 121.6 . . ?
C5 C6 H6A 121.6 . . ?
O5 C7 N3 127.6(5) . . ?
O5 C7 C8 125.2(4) . . ?
N3 C7 C8 107.1(4) . . ?
N2 C8 C9 115.9(4) . . ?
N2 C8 C7 110.5(4) . . ?
C9 C8 C7 103.1(4) . . ?
N2 C8 C21 108.5(4) . . ?
C9 C8 C21 111.3(4) . . ?
C7 C8 C21 107.2(4) . . ?
C10 C9 C14 119.9(4) . . ?
C10 C9 C8 132.3(5) . . ?
C14 C9 C8 107.7(4) . . ?
C9 C10 C11 117.8(5) . . ?
C9 C10 H10A 121.1 . . ?
C11 C10 H10A 121.1 . . ?
C12 C11 C10 123.1(5) . . ?
C12 C11 Br1 118.0(4) . . ?
C10 C11 Br1 119.0(4) . . ?
C11 C12 C13 119.3(4) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C14 C13 C12 117.5(5) . . ?
C14 C13 H13A 121.2 . . ?
C12 C13 H13A 121.2 . . ?
C13 C14 N3 127.3(5) . . ?
C13 C14 C9 122.2(5) . . ?
N3 C14 C9 110.4(4) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O4 127.5(5) . . ?
O3 C16 N2 122.8(4) . . ?
O4 C16 N2 109.6(4) . . ?
C18 C17 O4 109.7(5) . . ?
C18 C17 C19 115.3(7) . . ?
O4 C17 C19 108.9(5) . . ?
C18 C17 C20 109.3(6) . . ?
O4 C17 C20 101.8(5) . . ?
C19 C17 C20 110.9(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 C1 110.1(4) . . ?
N1 C21 C22 108.3(4) . . ?
C1 C21 C22 111.2(4) . . ?
N1 C21 C8 105.1(4) . . ?
C1 C21 C8 113.4(4) . . ?
C22 C21 C8 108.5(4) . . ?
O1 C22 O2 125.1(5) . . ?
O1 C22 C21 121.8(5) . . ?
O2 C22 C21 113.1(4) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 O2 C23 114.7(5) . . ?
C16 O4 C17 121.1(4) . . ?
Cl2 C01 Cl1 111.7(9) . . ?
Cl2 C01 H01B 109.3 . . ?
Cl1 C01 H01B 109.3 . . ?
Cl2 C01 H01A 109.3 . . ?
Cl1 C01 H01A 109.3 . . ?
H01B C01 H01A 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(10) . . . . ?
C21 C1 C2 C3 -175.6(7) . . . . ?
C1 C2 C3 C4 0.0(12) . . . . ?
C2 C3 C4 C5 2.4(13) . . . . ?
C3 C4 C5 C6 -5.3(14) . . . . ?
C2 C1 C6 C5 -2.7(10) . . . . ?
C21 C1 C6 C5 173.1(6) . . . . ?
C4 C5 C6 C1 5.4(13) . . . . ?
C14 N3 C7 O5 -177.2(5) . . . . ?
C15 N3 C7 O5 0.7(9) . . . . ?
C14 N3 C7 C8 5.7(6) . . . . ?
C15 N3 C7 C8 -176.4(5) . . . . ?
C16 N2 C8 C9 -65.4(6) . . . . ?
C16 N2 C8 C7 51.4(6) . . . . ?
C16 N2 C8 C21 168.7(4) . . . . ?
O5 C7 C8 N2 52.0(7) . . . . ?
N3 C7 C8 N2 -130.8(4) . . . . ?
O5 C7 C8 C9 176.5(5) . . . . ?
N3 C7 C8 C9 -6.3(5) . . . . ?
O5 C7 C8 C21 -66.0(6) . . . . ?
N3 C7 C8 C21 111.2(4) . . . . ?
N2 C8 C9 C10 -55.6(8) . . . . ?
C7 C8 C9 C10 -176.5(5) . . . . ?
C21 C8 C9 C10 68.9(7) . . . . ?
N2 C8 C9 C14 125.6(5) . . . . ?
C7 C8 C9 C14 4.7(5) . . . . ?
C21 C8 C9 C14 -109.9(5) . . . . ?
C14 C9 C10 C11 -0.1(7) . . . . ?
C8 C9 C10 C11 -178.8(5) . . . . ?
C9 C10 C11 C12 -1.9(7) . . . . ?
C9 C10 C11 Br1 178.6(4) . . . . ?
C10 C11 C12 C13 2.0(7) . . . . ?
Br1 C11 C12 C13 -178.5(4) . . . . ?
C11 C12 C13 C14 -0.1(7) . . . . ?
C12 C13 C14 N3 -178.7(5) . . . . ?
C12 C13 C14 C9 -1.9(8) . . . . ?
C7 N3 C14 C13 174.4(5) . . . . ?
C15 N3 C14 C13 -3.4(9) . . . . ?
C7 N3 C14 C9 -2.7(6) . . . . ?
C15 N3 C14 C9 179.5(5) . . . . ?
C10 C9 C14 C13 2.1(8) . . . . ?
C8 C9 C14 C13 -179.0(5) . . . . ?
C10 C9 C14 N3 179.4(5) . . . . ?
C8 C9 C14 N3 -1.7(5) . . . . ?
C8 N2 C16 O3 21.0(8) . . . . ?
C8 N2 C16 O4 -158.0(4) . . . . ?
C24 N1 C21 C1 -179(100) . . . . ?
C24 N1 C21 C22 -57(12) . . . . ?
C24 N1 C21 C8 58(11) . . . . ?
C2 C1 C21 N1 -14.2(7) . . . . ?
C6 C1 C21 N1 170.0(5) . . . . ?
C2 C1 C21 C22 -134.3(5) . . . . ?
C6 C1 C21 C22 49.9(6) . . . . ?
C2 C1 C21 C8 103.1(5) . . . . ?
C6 C1 C21 C8 -72.7(6) . . . . ?
N2 C8 C21 N1 -173.8(4) . . . . ?
C9 C8 C21 N1 57.6(5) . . . . ?
C7 C8 C21 N1 -54.4(5) . . . . ?
N2 C8 C21 C1 65.9(5) . . . . ?
C9 C8 C21 C1 -62.6(5) . . . . ?
C7 C8 C21 C1 -174.7(4) . . . . ?
N2 C8 C21 C22 -58.1(5) . . . . ?
C9 C8 C21 C22 173.3(4) . . . . ?
C7 C8 C21 C22 61.2(5) . . . . ?
N1 C21 C22 O1 -179.9(5) . . . . ?
C1 C21 C22 O1 -58.9(6) . . . . ?
C8 C21 C22 O1 66.5(6) . . . . ?
N1 C21 C22 O2 0.9(6) . . . . ?
C1 C21 C22 O2 122.0(5) . . . . ?
C8 C21 C22 O2 -112.6(5) . . . . ?
O1 C22 O2 C23 -6.4(8) . . . . ?
C21 C22 O2 C23 172.7(5) . . . . ?
O3 C16 O4 C17 3.0(8) . . . . ?
N2 C16 O4 C17 -178.0(4) . . . . ?
C18 C17 O4 C16 -55.8(7) . . . . ?
C19 C17 O4 C16 71.3(7) . . . . ?
C20 C17 O4 C16 -171.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.843
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.097
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: mixture of dichloromethane and petroleum ether'
