# 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_wei-xin-5
_database_code_depnum_ccdc_archive 'CCDC 1043112'
_audit_update_record             
;
2015-01-11 deposited with the CCDC.
2015-08-13 downloaded from the CCDC.
;
_audit_creation_date             2014-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'6-(4-Bromo-phenyl)-3-fluoro-5-nitro-2-oxo-4-phenyl-piperidine-3-carboxylic acid ethyl ester'
_chemical_formula_moiety         'C20 H18 Br F N2 O5'
_chemical_formula_sum            'C20 H18 Br F N2 O5'
_chemical_formula_weight         465.27
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 F N2 O5 Br'
_chemical_oxdiff_usercomment     "Wei's Wei-Xin-5"
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   22.744(3)
_cell_length_b                   7.5503(4)
_cell_length_c                   16.0634(18)
_cell_angle_alpha                90
_cell_angle_beta                 131.075(18)
_cell_angle_gamma                90
_cell_volume                     2079.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2133
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.3550
_cell_measurement_theta_min      3.6460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and hexanes'
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3936
_diffrn_reflns_point_group_measured_fraction_full 0.758
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.104
_diffrn_reflns_theta_min         3.650
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0416
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -63.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2322  -99.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   59.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   44.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   91.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
 10 omega  100.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
 11 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2322  178.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  -67.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega -106.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   54.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   74.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   51.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 19 omega   53.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.2322 -178.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 20 omega  -77.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -178.0000  -60.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0120175000
_diffrn_orient_matrix_UB_12      -0.2007431000
_diffrn_orient_matrix_UB_13      0.0001951000
_diffrn_orient_matrix_UB_21      -0.0663629000
_diffrn_orient_matrix_UB_22      0.0038838000
_diffrn_orient_matrix_UB_23      -0.1263617000
_diffrn_orient_matrix_UB_31      0.0593791000
_diffrn_orient_matrix_UB_32      -0.0363985000
_diffrn_orient_matrix_UB_33      -0.0146833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.384
_reflns_Friedel_fraction_full    0.474
_reflns_Friedel_fraction_max     0.445
_reflns_number_gt                2872
_reflns_number_total             2972
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0828P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1329
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 -0.19087(3) 0.58663(11) -0.07922(5) 0.0513(3) Uani 1 1 d . . . . .
F1 F 0.31525(19) 0.7926(4) 0.3454(2) 0.0277(7) Uani 1 1 d . . . . .
O1 O 0.3060(2) 0.6510(7) 0.5054(3) 0.0450(11) Uani 1 1 d . . . . .
O2 O 0.3848(2) 1.0447(6) 0.5781(3) 0.0389(11) Uani 1 1 d . . . . .
O3 O 0.4423(2) 0.8836(6) 0.5324(3) 0.0305(9) Uani 1 1 d . . . . .
O4 O 0.0946(3) 1.1481(7) 0.0786(4) 0.0506(12) Uani 1 1 d . . . . .
O5 O 0.1141(3) 1.2639(6) 0.2166(5) 0.0516(12) Uani 1 1 d . . . . .
N1 N 0.1881(2) 0.7714(7) 0.3698(3) 0.0282(10) Uani 1 1 d . . . . .
H1 H 0.1663 0.6846 0.3777 0.034 Uiso 1 1 calc R . . . .
N2 N 0.1222(2) 1.1458(6) 0.1732(4) 0.0285(9) Uani 1 1 d . . . . .
C1 C 0.2655(3) 0.7619(8) 0.4332(4) 0.0290(11) Uani 1 1 d . . . . .
C2 C 0.3034(3) 0.8920(7) 0.4073(4) 0.0214(10) Uani 1 1 d . . . . .
C3 C 0.2541(2) 1.0547(7) 0.3394(4) 0.0208(10) Uani 1 1 d . . . . .
H3 H 0.2513 1.1315 0.3875 0.025 Uiso 1 1 calc R . . . .
C4 C 0.1715(3) 0.9891(7) 0.2438(4) 0.0197(9) Uani 1 1 d . . . . .
H4 H 0.1726 0.8996 0.1989 0.024 Uiso 1 1 calc R . . . .
C5 C 0.1349(3) 0.9078(7) 0.2889(4) 0.0209(9) Uani 1 1 d . . . . .
H5 H 0.1292 1.0026 0.3267 0.025 Uiso 1 1 calc R . . . .
C6 C 0.0552(3) 0.8265(7) 0.1977(4) 0.0211(9) Uani 1 1 d . . . . .
C7 C -0.0111(3) 0.9252(8) 0.1529(4) 0.0298(11) Uani 1 1 d . . . . .
H7 H -0.0064 1.0420 0.1785 0.036 Uiso 1 1 calc R . . . .
C8 C -0.0850(3) 0.8521(9) 0.0695(5) 0.0368(13) Uani 1 1 d . . . . .
H8 H -0.1307 0.9195 0.0378 0.044 Uiso 1 1 calc R . . . .
C9 C -0.0907(3) 0.6843(9) 0.0344(4) 0.0318(12) Uani 1 1 d . . . . .
C10 C -0.0258(3) 0.5836(9) 0.0778(4) 0.0302(10) Uani 1 1 d . . . . .
H10 H -0.0311 0.4667 0.0518 0.036 Uiso 1 1 calc R . . . .
C11 C 0.0486(3) 0.6566(7) 0.1612(4) 0.0259(10) Uani 1 1 d . . . . .
H11 H 0.0940 0.5889 0.1922 0.031 Uiso 1 1 calc R . . . .
C12 C 0.2910(3) 1.1633(7) 0.3043(4) 0.0258(10) Uani 1 1 d . . . . .
C13 C 0.2863(3) 1.1110(8) 0.2172(4) 0.0300(11) Uani 1 1 d . . . . .
H13 H 0.2576 1.0080 0.1759 0.036 Uiso 1 1 calc R . . . .
C14 C 0.3235(4) 1.2090(9) 0.1903(5) 0.0388(14) Uani 1 1 d . . . . .
H14 H 0.3201 1.1733 0.1305 0.047 Uiso 1 1 calc R . . . .
C15 C 0.3658(4) 1.3592(9) 0.2510(6) 0.0446(16) Uani 1 1 d . . . . .
H15 H 0.3914 1.4257 0.2327 0.054 Uiso 1 1 calc R . . . .
C16 C 0.3710(4) 1.4127(9) 0.3378(7) 0.0471(16) Uani 1 1 d . . . . .
H16 H 0.4002 1.5152 0.3794 0.057 Uiso 1 1 calc R . . . .
C17 C 0.3328(3) 1.3144(8) 0.3637(5) 0.0338(12) Uani 1 1 d . . . . .
H17 H 0.3356 1.3515 0.4227 0.041 Uiso 1 1 calc R . . . .
C18 C 0.3817(3) 0.9497(7) 0.5162(4) 0.0232(10) Uani 1 1 d . . . . .
C19 C 0.5186(3) 0.9350(11) 0.6367(5) 0.0415(15) Uani 1 1 d . . . . .
H19A H 0.5172 1.0606 0.6530 0.050 Uiso 1 1 calc R . . . .
H19B H 0.5587 0.9226 0.6301 0.050 Uiso 1 1 calc R . . . .
C20 C 0.5394(4) 0.8208(12) 0.7285(5) 0.0524(18) Uani 1 1 d . . . . .
H20A H 0.5952 0.8321 0.7923 0.079 Uiso 1 1 calc GR . . . .
H20B H 0.5272 0.6970 0.7041 0.079 Uiso 1 1 calc GR . . . .
H20C H 0.5094 0.8582 0.7494 0.079 Uiso 1 1 calc GR . . . .


_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 C9 1.897(5) . ?
F1 C2 1.405(5) . ?
O1 C1 1.221(7) . ?
O2 C18 1.189(6) . ?
O3 C18 1.321(6) . ?
O3 C19 1.465(7) . ?
O4 N2 1.204(6) . ?
O5 N2 1.219(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.336(7) . ?
N1 C5 1.466(7) . ?
N2 C4 1.507(6) . ?
C1 C2 1.534(7) . ?
C2 C3 1.533(7) . ?
C2 C18 1.526(7) . ?
C3 H3 1.0000 . ?
C3 C4 1.531(6) . ?
C3 C12 1.523(7) . ?
C4 H4 1.0000 . ?
C4 C5 1.546(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.523(7) . ?
C6 C7 1.385(7) . ?
C6 C11 1.377(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.358(9) . ?
C9 C10 1.375(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.408(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(7) . ?
C12 C17 1.388(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(10) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(8) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.492(9) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C18 O3 C19 115.1(4) . . ?
C1 N1 H1 115.8 . . ?
C1 N1 C5 128.4(5) . . ?
C5 N1 H1 115.8 . . ?
O4 N2 O5 124.2(5) . . ?
O4 N2 C4 118.3(5) . . ?
O5 N2 C4 117.5(4) . . ?
O1 C1 N1 123.6(5) . . ?
O1 C1 C2 119.3(5) . . ?
N1 C1 C2 116.9(4) . . ?
F1 C2 C1 104.7(4) . . ?
F1 C2 C3 108.4(3) . . ?
F1 C2 C18 110.1(4) . . ?
C3 C2 C1 115.3(4) . . ?
C18 C2 C1 108.1(4) . . ?
C18 C2 C3 110.1(4) . . ?
C2 C3 H3 107.7 . . ?
C4 C3 C2 107.2(4) . . ?
C4 C3 H3 107.7 . . ?
C12 C3 C2 111.8(4) . . ?
C12 C3 H3 107.7 . . ?
C12 C3 C4 114.5(4) . . ?
N2 C4 C3 108.5(4) . . ?
N2 C4 H4 110.3 . . ?
N2 C4 C5 107.5(4) . . ?
C3 C4 H4 110.3 . . ?
C3 C4 C5 110.0(4) . . ?
C5 C4 H4 110.3 . . ?
N1 C5 C4 108.0(4) . . ?
N1 C5 H5 109.0 . . ?
N1 C5 C6 109.7(4) . . ?
C4 C5 H5 109.0 . . ?
C6 C5 C4 112.2(4) . . ?
C6 C5 H5 109.0 . . ?
C7 C6 C5 119.0(5) . . ?
C11 C6 C5 120.8(4) . . ?
C11 C6 C7 120.2(5) . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 Br1 119.3(5) . . ?
C8 C9 C10 121.8(5) . . ?
C10 C9 Br1 118.9(5) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(6) . . ?
C11 C10 H10 120.5 . . ?
C6 C11 C10 119.7(5) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C3 121.7(5) . . ?
C17 C12 C3 118.9(5) . . ?
C17 C12 C13 119.4(5) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(6) . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 120.7(6) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
O2 C18 O3 125.5(5) . . ?
O2 C18 C2 121.0(4) . . ?
O3 C18 C2 113.4(4) . . ?
O3 C19 H19A 109.6 . . ?
O3 C19 H19B 109.6 . . ?
O3 C19 C20 110.2(6) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 2.01 2.864(6) 162.2 4_546
C5 H5 O1 1.00 2.34 3.203(6) 143.8 4_556
C11 H11 O5 0.95 2.48 3.172(7) 129.7 1_545
C19 H19B O3 0.99 2.61 3.390(7) 135.6 2_656

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 C9 C10 C11 179.3(4) . . . . ?
F1 C2 C3 C4 70.8(4) . . . . ?
F1 C2 C3 C12 -55.4(5) . . . . ?
F1 C2 C18 O2 175.3(5) . . . . ?
F1 C2 C18 O3 -5.0(6) . . . . ?
O1 C1 C2 F1 76.7(6) . . . . ?
O1 C1 C2 C3 -164.3(5) . . . . ?
O1 C1 C2 C18 -40.6(7) . . . . ?
O4 N2 C4 C3 117.9(5) . . . . ?
O4 N2 C4 C5 -123.2(5) . . . . ?
O5 N2 C4 C3 -60.9(5) . . . . ?
O5 N2 C4 C5 58.0(6) . . . . ?
N1 C1 C2 F1 -99.6(5) . . . . ?
N1 C1 C2 C3 19.4(7) . . . . ?
N1 C1 C2 C18 143.1(5) . . . . ?
N1 C5 C6 C7 143.1(5) . . . . ?
N1 C5 C6 C11 -36.0(6) . . . . ?
N2 C4 C5 N1 -172.1(4) . . . . ?
N2 C4 C5 C6 66.8(5) . . . . ?
C1 N1 C5 C4 27.8(7) . . . . ?
C1 N1 C5 C6 150.4(5) . . . . ?
C1 C2 C3 C4 -46.1(5) . . . . ?
C1 C2 C3 C12 -172.3(4) . . . . ?
C1 C2 C18 O2 -71.0(6) . . . . ?
C1 C2 C18 O3 108.8(5) . . . . ?
C2 C3 C4 N2 -178.1(3) . . . . ?
C2 C3 C4 C5 64.6(5) . . . . ?
C2 C3 C12 C13 77.6(6) . . . . ?
C2 C3 C12 C17 -99.9(6) . . . . ?
C3 C2 C18 O2 55.7(6) . . . . ?
C3 C2 C18 O3 -124.5(4) . . . . ?
C3 C4 C5 N1 -54.2(5) . . . . ?
C3 C4 C5 C6 -175.3(4) . . . . ?
C3 C12 C13 C14 -177.2(5) . . . . ?
C3 C12 C17 C16 176.7(5) . . . . ?
C4 C3 C12 C13 -44.6(6) . . . . ?
C4 C3 C12 C17 137.9(5) . . . . ?
C4 C5 C6 C7 -96.9(5) . . . . ?
C4 C5 C6 C11 84.1(6) . . . . ?
C5 N1 C1 O1 173.5(5) . . . . ?
C5 N1 C1 C2 -10.4(8) . . . . ?
C5 C6 C7 C8 -179.5(5) . . . . ?
C5 C6 C11 C10 179.2(4) . . . . ?
C6 C7 C8 C9 0.6(8) . . . . ?
C7 C6 C11 C10 0.2(7) . . . . ?
C7 C8 C9 Br1 -179.6(4) . . . . ?
C7 C8 C9 C10 -0.6(9) . . . . ?
C8 C9 C10 C11 0.3(8) . . . . ?
C9 C10 C11 C6 -0.1(7) . . . . ?
C11 C6 C7 C8 -0.4(8) . . . . ?
C12 C3 C4 N2 -53.5(5) . . . . ?
C12 C3 C4 C5 -170.8(4) . . . . ?
C12 C13 C14 C15 0.3(9) . . . . ?
C13 C12 C17 C16 -0.9(8) . . . . ?
C13 C14 C15 C16 -0.3(10) . . . . ?
C14 C15 C16 C17 -0.3(10) . . . . ?
C15 C16 C17 C12 0.9(10) . . . . ?
C17 C12 C13 C14 0.3(8) . . . . ?
C18 O3 C19 C20 81.8(7) . . . . ?
C18 C2 C3 C4 -168.7(3) . . . . ?
C18 C2 C3 C12 65.1(5) . . . . ?
C19 O3 C18 O2 0.2(8) . . . . ?
C19 O3 C18 C2 -179.6(5) . . . . ?

