# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_mo_b0269_0m
_database_code_depnum_ccdc_archive 'CCDC 1472155'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;
_audit_creation_date             2016-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
"3'-benzyl 1'-(tert-butyl) (R)-5-bromo-1-methyl-2-oxo-1,2,5'-trihydrospiro[indole-3,2'-pyrrole]-1',3'-dicarboxylate"
_chemical_formula_moiety         'C25 H25 Br N2 O5'
_chemical_formula_sum            'C25 H25 Br N2 O5'
_chemical_formula_weight         513.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.001(2)
_cell_length_b                   9.362(2)
_cell_length_c                   14.597(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.810(8)
_cell_angle_gamma                90
_cell_volume                     1189.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    468
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.56
_cell_measurement_theta_min      3.20
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.767
_exptl_absorpt_correction_T_max  0.1259
_exptl_absorpt_correction_T_min  0.0878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0985 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.6974. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.146
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51392
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.993
_diffrn_reflns_theta_min         2.415
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker D8 VENTURE area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS PHOTON100 area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6144
_reflns_number_total             6317
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0072(15)
_refine_ls_extinction_coef       0.0076(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0207
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.2997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0530
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C16(H16), C17(H17), C5(H5), C11(H11), C18(H18), C20(H20), C7(H7),
 C19(H19)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.43964(2) 0.73281(2) 1.00684(2) 0.02615(7) Uani 1 1 d . . . . .
O3 O 0.79958(17) 0.18909(15) 0.85565(11) 0.0195(3) Uani 1 1 d . . . . .
O5 O 0.11638(16) 0.43180(16) 0.59239(11) 0.0187(3) Uani 1 1 d . . . . .
O2 O 0.83441(15) 0.41544(15) 0.80362(10) 0.0178(3) Uani 1 1 d . . . . .
O1 O 0.62807(17) 0.43673(17) 0.55827(11) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.65134(18) 0.64041(18) 0.65126(12) 0.0151(3) Uani 1 1 d . . . . .
O4 O 0.29267(16) 0.59709(16) 0.57728(11) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.61078(18) 0.30520(17) 0.74874(12) 0.0161(3) Uani 1 1 d . . . . .
C23 C 1.0218(3) 0.5941(3) 0.8435(2) 0.0338(6) Uani 1 1 d . . . . .
H23A H 1.0360 0.5856 0.7793 0.051 Uiso 1 1 calc GR . . . .
H23B H 1.1175 0.6276 0.8867 0.051 Uiso 1 1 calc GR . . . .
H23C H 0.9393 0.6626 0.8432 0.051 Uiso 1 1 calc GR . . . .
C4 C 0.6408(2) 0.8099(2) 0.78300(15) 0.0172(4) Uani 1 1 d . . . . .
H4 H 0.6898 0.8866 0.7596 0.021 Uiso 1 1 calc R . . . .
C15 C -0.0470(2) 0.4958(2) 0.43540(15) 0.0161(4) Uani 1 1 d . . . . .
C22 C 0.9791(2) 0.4482(2) 0.87647(15) 0.0194(4) Uani 1 1 d . . . . .
C16 C 0.0350(2) 0.5603(2) 0.37683(17) 0.0225(4) Uani 1 1 d . . . . .
H16 H 0.1165 0.6245 0.4029 0.027 Uiso 1 1 calc R . . . .
C3 C 0.6149(2) 0.6802(2) 0.73586(14) 0.0139(3) Uani 1 1 d . . . . .
C17 C -0.0037(3) 0.5298(3) 0.27956(18) 0.0277(5) Uani 1 1 d . . . . .
H17 H 0.0520 0.5734 0.2399 0.033 Uiso 1 1 calc R . . . .
C10 C 0.3756(2) 0.3846(2) 0.66239(13) 0.0136(3) Uani 1 1 d . . . . .
C8 C 0.5465(2) 0.56495(19) 0.77073(13) 0.0128(3) Uani 1 1 d . . . . .
C6 C 0.5190(2) 0.7110(2) 0.89859(13) 0.0172(4) Uani 1 1 d . . . . .
C24 C 1.1028(2) 0.3391(3) 0.87299(17) 0.0258(4) Uani 1 1 d . . . . .
H24A H 1.0766 0.2471 0.8968 0.039 Uiso 1 1 calc GR . . . .
H24B H 1.2020 0.3720 0.9125 0.039 Uiso 1 1 calc GR . . . .
H24C H 1.1096 0.3279 0.8074 0.039 Uiso 1 1 calc GR . . . .
C5 C 0.5918(2) 0.8241(2) 0.86693(14) 0.0190(4) Uani 1 1 d . . . . .
H5 H 0.6086 0.9111 0.9016 0.023 Uiso 1 1 calc R . . . .
C13 C 0.2597(2) 0.4838(2) 0.60627(13) 0.0151(3) Uani 1 1 d . . . . .
C11 C 0.3586(2) 0.2462(3) 0.68009(13) 0.0167(3) Uani 1 1 d . . . . .
H11 H 0.2643 0.1955 0.6609 0.020 Uiso 1 1 calc R . . . .
C18 C -0.1229(3) 0.4362(3) 0.24101(17) 0.0275(5) Uani 1 1 d . . . . .
H18 H -0.1486 0.4159 0.1751 0.033 Uiso 1 1 calc R . . . .
C1 C 0.6114(2) 0.5006(2) 0.62750(14) 0.0153(3) Uani 1 1 d . . . . .
C25 C 0.9449(3) 0.4565(3) 0.97284(19) 0.0350(6) Uani 1 1 d . . . . .
H25A H 0.8605 0.5238 0.9700 0.052 Uiso 1 1 calc GR . . . .
H25B H 1.0367 0.4894 1.0200 0.052 Uiso 1 1 calc GR . . . .
H25C H 0.9156 0.3618 0.9908 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.5068(2) 0.1815(2) 0.73394(15) 0.0191(4) Uani 1 1 d . . . . .
H12A H 0.4982 0.1409 0.7950 0.023 Uiso 1 1 calc R . . . .
H12B H 0.5415 0.1061 0.6966 0.023 Uiso 1 1 calc R . . . .
C2 C 0.7005(2) 0.7418(3) 0.58892(14) 0.0234(4) Uani 1 1 d . . . . .
H2A H 0.6244 0.8185 0.5716 0.035 Uiso 1 1 calc GR . . . .
H2B H 0.7100 0.6924 0.5315 0.035 Uiso 1 1 calc GR . . . .
H2C H 0.8002 0.7825 0.6218 0.035 Uiso 1 1 calc GR . . . .
C20 C -0.1667(2) 0.4020(2) 0.39616(15) 0.0178(4) Uani 1 1 d . . . . .
H20 H -0.2227 0.3580 0.4356 0.021 Uiso 1 1 calc R . . . .
C14 C -0.0079(2) 0.5244(2) 0.54077(15) 0.0195(4) Uani 1 1 d . . . . .
H14A H 0.0234 0.6255 0.5527 0.023 Uiso 1 1 calc R . . . .
H14B H -0.1003 0.5085 0.5645 0.023 Uiso 1 1 calc R . . . .
C21 C 0.7546(2) 0.2956(2) 0.80813(14) 0.0154(3) Uani 1 1 d . . . . .
C7 C 0.4956(2) 0.5786(2) 0.85200(14) 0.0150(3) Uani 1 1 d . . . . .
H7 H 0.4468 0.5017 0.8753 0.018 Uiso 1 1 calc R . . . .
C9 C 0.5377(2) 0.43751(19) 0.70472(13) 0.0126(3) Uani 1 1 d . . . . .
C19 C -0.2046(3) 0.3723(2) 0.29903(16) 0.0239(4) Uani 1 1 d . . . . .
H19 H -0.2863 0.3084 0.2726 0.029 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 C6 1.9042(19) . ?
O3 C21 1.223(2) . ?
O5 C13 1.345(2) . ?
O5 C14 1.463(2) . ?
O2 C22 1.487(2) . ?
O2 C21 1.343(2) . ?
O1 C1 1.216(2) . ?
N1 C3 1.407(3) . ?
N1 C1 1.378(3) . ?
N1 C2 1.460(3) . ?
O4 C13 1.206(3) . ?
N2 C12 1.469(2) . ?
N2 C21 1.365(2) . ?
N2 C9 1.471(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C22 1.530(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.386(3) . ?
C4 C5 1.411(3) . ?
C15 C16 1.401(3) . ?
C15 C20 1.394(3) . ?
C15 C14 1.511(3) . ?
C22 C24 1.522(3) . ?
C22 C25 1.517(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.402(3) . ?
C3 C8 1.401(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(4) . ?
C10 C13 1.478(3) . ?
C10 C11 1.338(3) . ?
C10 C9 1.515(2) . ?
C8 C7 1.383(3) . ?
C8 C9 1.523(3) . ?
C6 C5 1.385(3) . ?
C6 C7 1.404(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.493(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C1 C9 1.563(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C19 1.399(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C7 H7 0.9500 . ?
C19 H19 0.9500 . ?

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
C13 O5 C14 116.13(16) . . ?
C21 O2 C22 121.24(15) . . ?
C3 N1 C2 123.44(17) . . ?
C1 N1 C3 111.61(16) . . ?
C1 N1 C2 124.17(18) . . ?
C12 N2 C9 113.73(15) . . ?
C21 N2 C12 120.44(16) . . ?
C21 N2 C9 125.35(16) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.62(18) . . ?
C5 C4 H4 121.2 . . ?
C16 C15 C14 121.50(19) . . ?
C20 C15 C16 119.5(2) . . ?
C20 C15 C14 118.98(18) . . ?
O2 C22 C23 101.75(17) . . ?
O2 C22 C24 110.63(17) . . ?
O2 C22 C25 109.02(17) . . ?
C24 C22 C23 110.08(19) . . ?
C25 C22 C23 111.9(2) . . ?
C25 C22 C24 112.9(2) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C4 C3 N1 128.37(17) . . ?
C4 C3 C8 121.89(18) . . ?
C8 C3 N1 109.73(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C13 C10 C9 119.35(16) . . ?
C11 C10 C13 128.05(17) . . ?
C11 C10 C9 112.57(16) . . ?
C3 C8 C9 109.28(16) . . ?
C7 C8 C3 120.90(17) . . ?
C7 C8 C9 129.80(17) . . ?
C5 C6 Br1 120.31(15) . . ?
C5 C6 C7 122.62(18) . . ?
C7 C6 Br1 117.05(14) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.82(18) . . ?
C6 C5 H5 120.1 . . ?
O5 C13 C10 111.69(17) . . ?
O4 C13 O5 125.30(18) . . ?
O4 C13 C10 123.01(17) . . ?
C10 C11 H11 124.4 . . ?
C10 C11 C12 111.30(17) . . ?
C12 C11 H11 124.4 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.9(2) . . ?
C19 C18 H18 120.0 . . ?
O1 C1 N1 126.64(19) . . ?
O1 C1 C9 125.35(18) . . ?
N1 C1 C9 108.00(16) . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C12 C11 102.01(16) . . ?
N2 C12 H12A 111.4 . . ?
N2 C12 H12B 111.4 . . ?
C11 C12 H12A 111.4 . . ?
C11 C12 H12B 111.4 . . ?
H12A C12 H12B 109.2 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C15 C20 H20 119.9 . . ?
C15 C20 C19 120.3(2) . . ?
C19 C20 H20 119.9 . . ?
O5 C14 C15 111.57(17) . . ?
O5 C14 H14A 109.3 . . ?
O5 C14 H14B 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O3 C21 O2 127.28(17) . . ?
O3 C21 N2 122.44(18) . . ?
O2 C21 N2 110.27(17) . . ?
C8 C7 C6 117.08(17) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
N2 C9 C10 100.33(14) . . ?
N2 C9 C8 115.99(15) . . ?
N2 C9 C1 114.10(15) . . ?
C10 C9 C8 113.77(15) . . ?
C10 C9 C1 111.83(15) . . ?
C8 C9 C1 101.37(15) . . ?
C18 C19 C20 120.1(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?

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
Br1 C6 C5 C4 -175.68(15) . . . . ?
Br1 C6 C7 C8 176.92(13) . . . . ?
O1 C1 C9 N2 55.3(2) . . . . ?
O1 C1 C9 C10 -57.7(2) . . . . ?
O1 C1 C9 C8 -179.26(18) . . . . ?
N1 C3 C8 C7 -177.96(17) . . . . ?
N1 C3 C8 C9 0.5(2) . . . . ?
N1 C1 C9 N2 -125.57(16) . . . . ?
N1 C1 C9 C10 121.42(16) . . . . ?
N1 C1 C9 C8 -0.14(18) . . . . ?
C4 C3 C8 C7 2.9(3) . . . . ?
C4 C3 C8 C9 -178.57(17) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C15 C20 C19 C18 0.1(3) . . . . ?
C22 O2 C21 O3 -16.1(3) . . . . ?
C22 O2 C21 N2 165.35(16) . . . . ?
C16 C15 C20 C19 0.1(3) . . . . ?
C16 C15 C14 O5 -84.6(2) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C3 N1 C1 O1 179.58(19) . . . . ?
C3 N1 C1 C9 0.5(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C8 C7 C6 -1.5(3) . . . . ?
C3 C8 C9 N2 123.92(17) . . . . ?
C3 C8 C9 C10 -120.43(17) . . . . ?
C3 C8 C9 C1 -0.23(18) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C10 C11 C12 N2 2.6(2) . . . . ?
C5 C4 C3 N1 179.35(19) . . . . ?
C5 C4 C3 C8 -1.7(3) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
C13 O5 C14 C15 91.4(2) . . . . ?
C13 C10 C11 C12 175.89(18) . . . . ?
C13 C10 C9 N2 -177.58(16) . . . . ?
C13 C10 C9 C8 57.9(2) . . . . ?
C13 C10 C9 C1 -56.2(2) . . . . ?
C11 C10 C13 O5 16.3(3) . . . . ?
C11 C10 C13 O4 -163.7(2) . . . . ?
C11 C10 C9 N2 0.6(2) . . . . ?
C11 C10 C9 C8 -123.95(18) . . . . ?
C11 C10 C9 C1 121.94(18) . . . . ?
C1 N1 C3 C4 178.38(19) . . . . ?
C1 N1 C3 C8 -0.6(2) . . . . ?
C12 N2 C21 O3 -4.8(3) . . . . ?
C12 N2 C21 O2 173.82(17) . . . . ?
C12 N2 C9 C10 1.2(2) . . . . ?
C12 N2 C9 C8 124.16(18) . . . . ?
C12 N2 C9 C1 -118.55(18) . . . . ?
C2 N1 C3 C4 -11.3(3) . . . . ?
C2 N1 C3 C8 169.64(17) . . . . ?
C2 N1 C1 O1 9.4(3) . . . . ?
C2 N1 C1 C9 -169.72(16) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C20 C15 C14 O5 94.8(2) . . . . ?
C14 O5 C13 O4 -2.4(3) . . . . ?
C14 O5 C13 C10 177.63(16) . . . . ?
C14 C15 C16 C17 179.3(2) . . . . ?
C14 C15 C20 C19 -179.38(19) . . . . ?
C21 O2 C22 C23 -177.94(18) . . . . ?
C21 O2 C22 C24 65.1(2) . . . . ?
C21 O2 C22 C25 -59.6(2) . . . . ?
C21 N2 C12 C11 170.25(17) . . . . ?
C21 N2 C9 C10 -170.92(18) . . . . ?
C21 N2 C9 C8 -47.9(3) . . . . ?
C21 N2 C9 C1 69.4(2) . . . . ?
C7 C8 C9 N2 -57.8(3) . . . . ?
C7 C8 C9 C10 57.9(3) . . . . ?
C7 C8 C9 C1 178.07(18) . . . . ?
C7 C6 C5 C4 2.1(3) . . . . ?
C9 N2 C12 C11 -2.3(2) . . . . ?
C9 N2 C21 O3 166.78(18) . . . . ?
C9 N2 C21 O2 -14.6(3) . . . . ?
C9 C10 C13 O5 -165.86(16) . . . . ?
C9 C10 C13 O4 14.1(3) . . . . ?
C9 C10 C11 C12 -2.1(2) . . . . ?
C9 C8 C7 C6 -179.67(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'Ethylacetate/ Petrolether'
