# Electronic Supplementary Material (ESI) for ChemComm.
# 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_4e
_database_code_depnum_ccdc_archive 'CCDC 1437688'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_date             2015-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H12 Br N O5'
_chemical_formula_sum            'C20 H12 Br N O5'
_chemical_formula_weight         426.22
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N1 O1 Br1'
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'
Br Br -0.6763 1.2805 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   5.25660(5)
_cell_length_b                   12.33003(13)
_cell_length_c                   25.5995(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1659.21(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15355
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      74.1650
_cell_measurement_theta_min      3.9780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.688
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3667
_exptl_crystal_size_mid          0.0463
_exptl_crystal_size_min          0.0403
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.713
_diffrn_reflns_theta_min         3.453
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   57.0000 -150.0000 99

#__ type_ start__ end____ width___ exp.time_
  4 omega   89.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   78.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  113.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega  152.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  139.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  153.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   69.0000 -154.9633 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  133.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   59.0000   13.7630 37

#__ type_ start__ end____ width___ exp.time_
 11 omega  133.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   63.0000   74.9322 45

#__ type_ start__ end____ width___ exp.time_
 12 omega  133.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  121.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
 14 omega  109.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 15 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   78.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 17 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   63.0000   74.9322 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   76.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   69.0000   34.6403 88

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   80.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
 22 omega   86.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   77.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   69.0000 -154.9633 27

#__ type_ start__ end____ width___ exp.time_
 24 omega   82.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   79.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   56.0000 -158.0661 91

#__ type_ start__ end____ width___ exp.time_
 26 omega  112.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   57.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 28 omega   41.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -77.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 29 omega   54.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
 30 omega   33.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
 31 omega   25.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
 32 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 33 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   74.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 37 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   59.0000   13.7630 26

#__ type_ start__ end____ width___ exp.time_
 38 omega   78.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 39 omega   74.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
 40 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 41 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 42 omega   74.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
 43 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega   75.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 46 omega    9.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
 47 omega   13.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega    9.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000 -180.0000 108

#__ type_ start__ end____ width___ exp.time_
 49 omega    2.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -99.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
 50 omega  -76.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 51 omega  -95.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
 52 omega -109.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 53 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000  -90.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2480526000
_diffrn_orient_matrix_UB_12      0.0646112000
_diffrn_orient_matrix_UB_13      0.0075730000
_diffrn_orient_matrix_UB_21      0.1189666000
_diffrn_orient_matrix_UB_22      -0.0594197000
_diffrn_orient_matrix_UB_23      -0.0469878000
_diffrn_orient_matrix_UB_31      -0.1006768000
_diffrn_orient_matrix_UB_32      0.0889293000
_diffrn_orient_matrix_UB_33      -0.0368612000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2801
_reflns_number_total             2936
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.046(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0206
_refine_ls_restrained_S_all      1.067
_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)+(0.0266P)²+0.5878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0537
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.51796(5) 0.50260(3) 0.71326(2) 0.02666(10) Uani 1 1 d . . . . .
O1 O 0.3805(4) 0.39469(15) 0.58936(7) 0.0183(4) Uani 1 1 d . . . . .
O2 O 0.7406(4) 0.31253(16) 0.52882(8) 0.0225(4) Uani 1 1 d . . . . .
O3 O 0.1398(4) 0.62262(17) 0.44972(8) 0.0239(4) Uani 1 1 d . . . . .
O4 O 0.5499(4) 0.65697(17) 0.59064(9) 0.0285(5) Uani 1 1 d . . . . .
O5 O 0.3179(4) 0.74531(18) 0.64552(8) 0.0299(5) Uani 1 1 d . . . . .
N1 N 0.3501(5) 0.69963(19) 0.60382(9) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.1719(5) 0.4303(2) 0.61886(10) 0.0169(5) Uani 1 1 d . . . . .
C2 C 0.1424(5) 0.3655(2) 0.66737(11) 0.0191(6) Uani 1 1 d . . . . .
C3 C -0.0413(6) 0.2840(2) 0.66911(12) 0.0259(6) Uani 1 1 d . . . . .
H3 H -0.1426 0.2711 0.6400 0.031 Uiso 1 1 calc R . . . .
C4 C -0.0749(6) 0.2219(2) 0.71395(13) 0.0304(7) Uani 1 1 d . . . . .
H4 H -0.1998 0.1685 0.7150 0.036 Uiso 1 1 calc R . . . .
C5 C 0.0793(7) 0.2402(3) 0.75706(12) 0.0299(7) Uani 1 1 d . . . . .
H5 H 0.0598 0.1976 0.7868 0.036 Uiso 1 1 calc R . . . .
C6 C 0.2617(6) 0.3210(3) 0.75625(12) 0.0278(7) Uani 1 1 d . . . . .
H6 H 0.3648 0.3332 0.7852 0.033 Uiso 1 1 calc R . . . .
C7 C 0.2882(5) 0.3834(2) 0.71166(11) 0.0229(6) Uani 1 1 d . . . . .
C8 C 0.0201(5) 0.5097(2) 0.60400(9) 0.0171(5) Uani 1 1 d . . . . .
H8 H -0.1186 0.5269 0.6250 0.021 Uiso 1 1 calc R . . . .
C9 C 0.0608(5) 0.5738(2) 0.55463(10) 0.0167(5) Uani 1 1 d . . . . .
H9 H -0.1002 0.5742 0.5353 0.020 Uiso 1 1 calc R . . . .
C10 C 0.1318(5) 0.6931(2) 0.56666(11) 0.0188(6) Uani 1 1 d . . . . .
H10A H 0.1764 0.7298 0.5344 0.023 Uiso 1 1 calc R . . . .
H10B H -0.0142 0.7299 0.5816 0.023 Uiso 1 1 calc R . . . .
C11 C 0.2550(5) 0.5159(2) 0.52144(10) 0.0166(5) Uani 1 1 d . . . . .
C12 C 0.3993(5) 0.4353(2) 0.54018(10) 0.0157(5) Uani 1 1 d . . . . .
C13 C 0.6062(5) 0.3818(2) 0.50920(11) 0.0175(5) Uani 1 1 d . . . . .
C14 C 0.6397(6) 0.4206(2) 0.45452(11) 0.0187(6) Uani 1 1 d . . . . .
C15 C 0.4794(5) 0.5004(2) 0.43387(9) 0.0187(5) Uani 1 1 d . . . . .
C16 C 0.2787(5) 0.5516(2) 0.46661(10) 0.0184(6) Uani 1 1 d . . . . .
C17 C 0.5113(6) 0.5350(2) 0.38253(11) 0.0239(6) Uani 1 1 d . . . . .
H17 H 0.4031 0.5871 0.3685 0.029 Uiso 1 1 calc R . . . .
C18 C 0.7049(6) 0.4916(3) 0.35247(11) 0.0285(6) Uani 1 1 d . . . . .
H18 H 0.7275 0.5151 0.3183 0.034 Uiso 1 1 calc R . . . .
C19 C 0.8645(7) 0.4136(3) 0.37285(12) 0.0298(7) Uani 1 1 d . . . . .
H19 H 0.9942 0.3851 0.3523 0.036 Uiso 1 1 calc R . . . .
C20 C 0.8334(6) 0.3770(2) 0.42410(12) 0.0236(6) Uani 1 1 d . . . . .
H20 H 0.9409 0.3242 0.4377 0.028 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 C7 1.903(3) . ?
O1 C1 1.402(3) . ?
O1 C12 1.359(3) . ?
O2 C13 1.217(3) . ?
O3 C16 1.219(4) . ?
O4 N1 1.222(3) . ?
O5 N1 1.219(3) . ?
N1 C10 1.493(4) . ?
C1 C2 1.485(4) . ?
C1 C8 1.319(4) . ?
C2 C3 1.394(4) . ?
C2 C7 1.386(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.506(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.549(4) . ?
C9 C11 1.508(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.339(4) . ?
C11 C16 1.476(4) . ?
C12 C13 1.499(4) . ?
C13 C14 1.490(4) . ?
C14 C15 1.399(4) . ?
C14 C20 1.390(4) . ?
C15 C16 1.489(4) . ?
C15 C17 1.392(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(4) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C1 116.1(2) . . ?
O4 N1 C10 117.5(2) . . ?
O5 N1 O4 124.1(3) . . ?
O5 N1 C10 118.5(2) . . ?
O1 C1 C2 111.3(2) . . ?
C8 C1 O1 123.4(2) . . ?
C8 C1 C2 125.3(2) . . ?
C3 C2 C1 119.2(3) . . ?
C7 C2 C1 122.7(3) . . ?
C7 C2 C3 118.1(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.9(3) . . ?
C7 C6 H6 120.6 . . ?
C2 C7 Br1 119.4(2) . . ?
C6 C7 Br1 118.4(2) . . ?
C6 C7 C2 122.0(3) . . ?
C1 C8 H8 118.5 . . ?
C1 C8 C9 123.1(2) . . ?
C9 C8 H8 118.5 . . ?
C8 C9 H9 107.6 . . ?
C8 C9 C10 111.5(2) . . ?
C8 C9 C11 108.7(2) . . ?
C10 C9 H9 107.6 . . ?
C11 C9 H9 107.6 . . ?
C11 C9 C10 113.5(2) . . ?
N1 C10 C9 111.3(2) . . ?
N1 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C9 122.2(2) . . ?
C12 C11 C16 120.9(2) . . ?
C16 C11 C9 116.9(2) . . ?
O1 C12 C13 112.4(2) . . ?
C11 C12 O1 124.3(2) . . ?
C11 C12 C13 123.2(2) . . ?
O2 C13 C12 120.8(2) . . ?
O2 C13 C14 123.0(2) . . ?
C14 C13 C12 116.2(2) . . ?
C15 C14 C13 120.6(2) . . ?
C20 C14 C13 119.3(3) . . ?
C20 C14 C15 120.1(3) . . ?
C14 C15 C16 120.8(2) . . ?
C17 C15 C14 120.0(3) . . ?
C17 C15 C16 119.1(3) . . ?
O3 C16 C11 120.1(3) . . ?
O3 C16 C15 122.0(2) . . ?
C11 C16 C15 117.9(2) . . ?
C15 C17 H17 120.2 . . ?
C18 C17 C15 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C14 C20 C19 119.2(3) . . ?
C14 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?

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
O1 C1 C2 C3 -101.1(3) . . . . ?
O1 C1 C2 C7 79.9(3) . . . . ?
O1 C1 C8 C9 -2.6(4) . . . . ?
O1 C12 C13 O2 -2.1(4) . . . . ?
O1 C12 C13 C14 179.5(2) . . . . ?
O2 C13 C14 C15 179.9(3) . . . . ?
O2 C13 C14 C20 -0.4(4) . . . . ?
O4 N1 C10 C9 59.1(3) . . . . ?
O5 N1 C10 C9 -119.8(3) . . . . ?
C1 O1 C12 C11 9.3(4) . . . . ?
C1 O1 C12 C13 -172.3(2) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C1 C2 C7 Br1 5.1(4) . . . . ?
C1 C2 C7 C6 -178.8(3) . . . . ?
C1 C8 C9 C10 -112.8(3) . . . . ?
C1 C8 C9 C11 13.1(4) . . . . ?
C2 C1 C8 C9 179.3(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C2 C7 Br1 -174.0(2) . . . . ?
C3 C2 C7 C6 2.1(4) . . . . ?
C3 C4 C5 C6 1.5(5) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 Br1 174.4(2) . . . . ?
C5 C6 C7 C2 -1.8(5) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C8 C1 C2 C3 77.3(4) . . . . ?
C8 C1 C2 C7 -101.8(4) . . . . ?
C8 C9 C10 N1 52.3(3) . . . . ?
C8 C9 C11 C12 -13.1(4) . . . . ?
C8 C9 C11 C16 166.5(2) . . . . ?
C9 C11 C12 O1 2.7(4) . . . . ?
C9 C11 C12 C13 -175.5(2) . . . . ?
C9 C11 C16 O3 -2.1(4) . . . . ?
C9 C11 C16 C15 176.5(2) . . . . ?
C10 C9 C11 C12 111.5(3) . . . . ?
C10 C9 C11 C16 -68.9(3) . . . . ?
C11 C9 C10 N1 -70.8(3) . . . . ?
C11 C12 C13 O2 176.3(3) . . . . ?
C11 C12 C13 C14 -2.1(4) . . . . ?
C12 O1 C1 C2 169.0(2) . . . . ?
C12 O1 C1 C8 -9.4(4) . . . . ?
C12 C11 C16 O3 177.5(3) . . . . ?
C12 C11 C16 C15 -4.0(4) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C12 C13 C14 C20 177.9(2) . . . . ?
C13 C14 C15 C16 2.5(4) . . . . ?
C13 C14 C15 C17 -179.4(3) . . . . ?
C13 C14 C20 C19 -179.9(3) . . . . ?
C14 C15 C16 O3 178.7(3) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C14 C15 C17 C18 -1.2(4) . . . . ?
C15 C14 C20 C19 -0.3(4) . . . . ?
C15 C17 C18 C19 0.6(4) . . . . ?
C16 C11 C12 O1 -176.9(2) . . . . ?
C16 C11 C12 C13 4.9(4) . . . . ?
C16 C15 C17 C18 177.0(3) . . . . ?
C17 C15 C16 O3 0.6(4) . . . . ?
C17 C15 C16 C11 -177.9(2) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C18 C19 C20 C14 -0.3(5) . . . . ?
C20 C14 C15 C16 -177.1(3) . . . . ?
C20 C14 C15 C17 1.0(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -5 -13 0.0148 -0.0023 -5.0012 -12.9985 -0.4221 0.9077 0.0346
0 5 13 0.0264 0.0023 5.0012 12.9985 0.4221 -0.9077 -0.0346
-1 7 -8 0.0903 -1.0013 7.0031 -7.9947 0.1436 -0.1596 1.0183
1 -6 8 0.1507 1.0013 -6.0027 7.9949 -0.0789 0.1001 -0.9293
3 0 -1 0.1882 2.9995 0.0003 -1.0071 0.7364 0.4041 -0.2648
-3 0 1 0.1785 -2.9995 -0.0003 1.0071 -0.7364 -0.4041 0.2648
0 6 -11 0.0265 -0.0019 6.0030 -10.9967 0.3041 0.1598 0.9394
0 -6 11 0.0161 0.0019 -6.0030 10.9967 -0.3041 -0.1598 -0.9394
0 8 6 0.0257 0.0011 8.0028 6.0004 0.5628 -0.7573 0.4904
1 6 11 0.0393 1.0018 6.0018 10.9966 0.7196 -0.7541 0.0275
0 -7 -8 0.0171 -0.0014 -7.0023 -7.9998 -0.5134 0.7918 -0.3277
0 1 -16 0.0197 -0.0028 1.0013 -15.9968 -0.0571 0.6918 0.6790
0 -6 -10 0.0132 -0.0018 -6.0018 -9.9993 -0.4639 0.8263 -0.1650
-1 -8 -2 0.0346 -1.0002 -8.0031 -1.9987 -0.7803 0.4505 -0.5373

_olex2_submission_special_instructions 'No special instructions were received'

