# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_47
_database_code_depnum_ccdc_archive 'CCDC 1886142'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_audit_creation_date             2016-08-03
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C19 H15 Br F5 N O2'
_chemical_formula_moiety         'C19 H15 Br F5 N O2'
_chemical_formula_weight         464.23
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.753(6)
_cell_length_b                   6.281(3)
_cell_length_c                   13.273(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.939(9)
_cell_angle_gamma                90.0000
_cell_volume                     958.6(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3090
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464.00
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.442
_exptl_absorpt_correction_T_max  0.936

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            10431
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_theta_max         25.319
_diffrn_reflns_theta_min         1.771
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3443
_reflns_number_gt                2979
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.976

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0617
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3443
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   0.697
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[σ²(Fo²)]'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(9)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br14 Br 0.91914(4) 0.44681(9) 1.15508(3) 0.02810(14) Uani 1 1 d . . . . .
F1 F 0.46691(19) -0.0698(6) 0.65849(17) 0.0248(6) Uani 1 1 d . . . . .
F2 F 0.6236(2) -0.1924(4) 0.7601(2) 0.0249(7) Uani 1 1 d . . . . .
F3 F 0.4076(3) 0.1215(5) 0.8330(3) 0.0345(9) Uani 1 1 d . . . . .
F4 F 0.4080(3) -0.2215(5) 0.8212(3) 0.0333(9) Uani 1 1 d . . . . .
F5 F 0.5457(2) -0.0627(7) 0.92623(17) 0.0322(6) Uani 1 1 d . . . . .
O1 O 0.5226(3) 0.3451(5) 0.7005(2) 0.0212(8) Uani 1 1 d . . . . .
O2 O 0.5501(3) 0.5242(5) 0.5558(2) 0.0276(9) Uani 1 1 d . . . . .
N8 N 1.1396(3) 0.2953(6) 0.6321(3) 0.0236(10) Uani 1 1 d . . . . .
C2 C 0.5746(4) 0.3836(8) 0.6158(4) 0.0222(12) Uani 1 1 d . . . . .
C3 C 0.6581(4) 0.1952(8) 0.6387(3) 0.0181(11) Uani 1 1 d . . . . .
H3 H 0.6273 0.0744 0.5919 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6079(4) 0.1788(8) 0.7405(4) 0.0188(12) Uani 1 1 d . . . . .
C5 C 0.7845(4) 0.2252(8) 0.6388(3) 0.0180(11) Uani 1 1 d . . . . .
C6 C 0.8444(4) 0.0681(7) 0.5975(3) 0.0204(11) Uani 1 1 d . . . . .
H6 H 0.8039 -0.0563 0.5694 0.024 Uiso 1 1 calc R U . . .
C7 C 0.9619(4) 0.0880(8) 0.5962(3) 0.0197(11) Uani 1 1 d . . . . .
H7 H 1.0005 -0.0236 0.5685 0.024 Uiso 1 1 calc R U . . .
C8 C 1.0240(4) 0.2707(7) 0.6353(3) 0.0171(11) Uani 1 1 d . . . . .
C9 C 0.9629(3) 0.4313(10) 0.6777(3) 0.0209(10) Uani 1 1 d . . . . .
H9 H 1.0028 0.5561 0.7060 0.025 Uiso 1 1 calc R U . . .
C10 C 0.8458(4) 0.4079(8) 0.6782(3) 0.0214(12) Uani 1 1 d . . . . .
H10 H 0.8063 0.5183 0.7060 0.026 Uiso 1 1 calc R U . . .
C11 C 0.6861(4) 0.2427(7) 0.8401(4) 0.0181(11) Uani 1 1 d . . . . .
C12 C 0.7883(4) 0.1307(8) 0.8798(4) 0.0223(12) Uani 1 1 d . . . . .
H12 H 0.8102 0.0140 0.8426 0.027 Uiso 1 1 calc R U . . .
C13 C 0.8579(4) 0.1892(8) 0.9737(4) 0.0223(12) Uani 1 1 d . . . . .
H13 H 0.9265 0.1111 1.0015 0.027 Uiso 1 1 calc R U . . .
C14 C 0.8261(4) 0.3622(8) 1.0257(3) 0.0202(11) Uani 1 1 d . . . . .
C15 C 0.7266(4) 0.4788(9) 0.9876(3) 0.0207(12) Uani 1 1 d . . . . .
H15 H 0.7068 0.5993 1.0236 0.025 Uiso 1 1 calc R U . . .
C16 C 0.6564(4) 0.4147(9) 0.8951(3) 0.0194(11) Uani 1 1 d . . . . .
H16 H 0.5866 0.4903 0.8690 0.023 Uiso 1 1 calc R U . . .
C17 C 0.5439(4) -0.0306(10) 0.7468(3) 0.0202(11) Uani 1 1 d . . . . .
C18 C 0.4755(4) -0.0490(11) 0.8339(3) 0.0232(10) Uani 1 1 d . . . . .
C19 C 1.2040(4) 0.1206(8) 0.5987(4) 0.0266(13) Uani 1 1 d . . . . .
H19A H 1.2844 0.1652 0.6011 0.032 Uiso 1 1 calc R U . . .
H19B H 1.2035 -0.0018 0.6444 0.032 Uiso 1 1 calc R U . . .
H19C H 1.1674 0.0804 0.5281 0.032 Uiso 1 1 calc R U . . .
C20 C 1.2057(4) 0.4717(11) 0.6871(4) 0.0327(13) Uani 1 1 d . . . . .
H20A H 1.2859 0.4664 0.6770 0.039 Uiso 1 1 calc R U . . .
H20B H 1.1699 0.6069 0.6604 0.039 Uiso 1 1 calc R U . . .
H20C H 1.2056 0.4604 0.7607 0.039 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br14 C14 1.910(5) . ?
F1 C17 1.347(5) . ?
F2 C17 1.368(6) . ?
F3 C18 1.334(6) . ?
F4 C18 1.332(7) . ?
F5 C18 1.331(4) . ?
O1 C2 1.407(5) . ?
O1 C4 1.468(5) . ?
O2 C2 1.184(5) . ?
N8 C8 1.378(6) . ?
N8 C19 1.453(6) . ?
N8 C20 1.459(6) . ?
C2 C3 1.528(6) . ?
C3 C5 1.497(6) . ?
C3 C4 1.586(6) . ?
C3 H3 1.0000 . ?
C4 C11 1.500(6) . ?
C4 C17 1.526(7) . ?
C5 C6 1.389(6) . ?
C5 C10 1.397(6) . ?
C6 C7 1.390(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.420(7) . ?
C9 C10 1.386(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.389(6) . ?
C11 C12 1.397(6) . ?
C12 C13 1.391(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(6) . ?
C15 C16 1.388(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.544(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
C2 O1 C4 92.0(3) . . ?
C8 N8 C19 120.2(4) . . ?
C8 N8 C20 119.7(4) . . ?
C19 N8 C20 118.0(4) . . ?
O2 C2 O1 125.5(5) . . ?
O2 C2 C3 140.2(5) . . ?
O1 C2 C3 94.3(4) . . ?
C5 C3 C2 119.9(4) . . ?
C5 C3 C4 123.5(4) . . ?
C2 C3 C4 83.3(3) . . ?
C5 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
O1 C4 C11 112.1(4) . . ?
O1 C4 C17 109.0(4) . . ?
C11 C4 C17 113.6(4) . . ?
O1 C4 C3 89.6(3) . . ?
C11 C4 C3 117.7(4) . . ?
C17 C4 C3 112.2(4) . . ?
C6 C5 C10 117.9(4) . . ?
C6 C5 C3 119.6(4) . . ?
C10 C5 C3 122.6(4) . . ?
C5 C6 C7 121.8(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N8 C8 C7 121.5(4) . . ?
N8 C8 C9 121.0(4) . . ?
C7 C8 C9 117.5(4) . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C16 C11 C12 118.8(4) . . ?
C16 C11 C4 119.8(4) . . ?
C12 C11 C4 121.4(4) . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.9(4) . . ?
C13 C14 Br14 120.3(4) . . ?
C15 C14 Br14 117.7(3) . . ?
C14 C15 C16 118.2(5) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C15 C16 C11 121.5(5) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
F1 C17 F2 107.2(4) . . ?
F1 C17 C4 111.1(4) . . ?
F2 C17 C4 108.4(3) . . ?
F1 C17 C18 106.1(3) . . ?
F2 C17 C18 107.2(4) . . ?
C4 C17 C18 116.4(5) . . ?
F5 C18 F4 107.7(5) . . ?
F5 C18 F3 108.4(5) . . ?
F4 C18 F3 108.2(3) . . ?
F5 C18 C17 112.0(3) . . ?
F4 C18 C17 110.8(5) . . ?
F3 C18 C17 109.7(5) . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 O1 C2 O2 -172.1(5) . . . . ?
C4 O1 C2 C3 7.5(4) . . . . ?
O2 C2 C3 C5 47.6(8) . . . . ?
O1 C2 C3 C5 -132.0(4) . . . . ?
O2 C2 C3 C4 172.5(6) . . . . ?
O1 C2 C3 C4 -7.0(3) . . . . ?
C2 O1 C4 C11 112.7(4) . . . . ?
C2 O1 C4 C17 -120.6(4) . . . . ?
C2 O1 C4 C3 -7.2(3) . . . . ?
C5 C3 C4 O1 128.3(4) . . . . ?
C2 C3 C4 O1 6.7(3) . . . . ?
C5 C3 C4 C11 13.5(7) . . . . ?
C2 C3 C4 C11 -108.2(4) . . . . ?
C5 C3 C4 C17 -121.2(5) . . . . ?
C2 C3 C4 C17 117.2(4) . . . . ?
C2 C3 C5 C6 -140.7(4) . . . . ?
C4 C3 C5 C6 116.7(5) . . . . ?
C2 C3 C5 C10 38.7(6) . . . . ?
C4 C3 C5 C10 -63.9(6) . . . . ?
C10 C5 C6 C7 0.9(7) . . . . ?
C3 C5 C6 C7 -179.7(4) . . . . ?
C5 C6 C7 C8 -1.1(7) . . . . ?
C19 N8 C8 C7 -7.2(7) . . . . ?
C20 N8 C8 C7 -170.8(4) . . . . ?
C19 N8 C8 C9 173.4(4) . . . . ?
C20 N8 C8 C9 9.8(7) . . . . ?
C6 C7 C8 N8 -178.2(4) . . . . ?
C6 C7 C8 C9 1.2(7) . . . . ?
N8 C8 C9 C10 178.3(4) . . . . ?
C7 C8 C9 C10 -1.1(7) . . . . ?
C8 C9 C10 C5 1.0(7) . . . . ?
C6 C5 C10 C9 -0.9(7) . . . . ?
C3 C5 C10 C9 179.8(4) . . . . ?
O1 C4 C11 C16 14.9(6) . . . . ?
C17 C4 C11 C16 -109.3(5) . . . . ?
C3 C4 C11 C16 116.7(5) . . . . ?
O1 C4 C11 C12 -165.9(4) . . . . ?
C17 C4 C11 C12 69.9(6) . . . . ?
C3 C4 C11 C12 -64.1(6) . . . . ?
C16 C11 C12 C13 0.9(7) . . . . ?
C4 C11 C12 C13 -178.3(4) . . . . ?
C11 C12 C13 C14 -1.4(7) . . . . ?
C12 C13 C14 C15 0.3(7) . . . . ?
C12 C13 C14 Br14 179.7(4) . . . . ?
C13 C14 C15 C16 1.4(7) . . . . ?
Br14 C14 C15 C16 -178.1(3) . . . . ?
C14 C15 C16 C11 -2.0(7) . . . . ?
C12 C11 C16 C15 0.8(7) . . . . ?
C4 C11 C16 C15 -180.0(4) . . . . ?
O1 C4 C17 F1 48.2(5) . . . . ?
C11 C4 C17 F1 174.1(4) . . . . ?
C3 C4 C17 F1 -49.3(5) . . . . ?
O1 C4 C17 F2 165.8(3) . . . . ?
C11 C4 C17 F2 -68.4(5) . . . . ?
C3 C4 C17 F2 68.2(5) . . . . ?
O1 C4 C17 C18 -73.3(5) . . . . ?
C11 C4 C17 C18 52.5(6) . . . . ?
C3 C4 C17 C18 -170.9(4) . . . . ?
F1 C17 C18 F5 165.5(5) . . . . ?
F2 C17 C18 F5 51.2(7) . . . . ?
C4 C17 C18 F5 -70.4(7) . . . . ?
F1 C17 C18 F4 45.3(6) . . . . ?
F2 C17 C18 F4 -69.1(5) . . . . ?
C4 C17 C18 F4 169.4(4) . . . . ?
F1 C17 C18 F3 -74.1(6) . . . . ?
F2 C17 C18 F3 171.6(4) . . . . ?
C4 C17 C18 F3 50.0(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_53
_database_code_depnum_ccdc_archive 'CCDC 1886144'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_audit_creation_date             2016-09-21
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C18 H15 Br F3 N O2'
_chemical_formula_moiety         'C18 H15 Br F3 N O2'
_chemical_formula_weight         414.22
_chemical_melting_point          ?
_chemical_absolute_configuration 'ad '

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2685(13)
_cell_length_b                   17.886(3)
_cell_length_c                   21.589(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3578.9(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7745
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664.00
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_T_max  0.791

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            20510
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         1.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6593
_reflns_number_gt                4683
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0655
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6593
_refine_ls_number_parameters     451
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0243P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br14 Br 0.32051(6) 0.34341(4) 0.29482(3) 0.03875(18) Uani 1 1 d . . . . .
Br34 Br 0.34868(6) 0.16357(3) 0.19600(3) 0.03746(18) Uani 1 1 d . . . . .
F1 F 0.8742(3) 0.12124(18) 0.52241(13) 0.0371(9) Uani 1 1 d . . . . .
F2 F 0.6875(3) 0.19332(19) 0.52495(13) 0.0424(9) Uani 1 1 d . . . . .
F3 F 0.8742(3) 0.22433(19) 0.46986(14) 0.0378(8) Uani 1 1 d . . . . .
F4 F 0.9421(3) 0.3865(2) -0.01287(14) 0.0394(9) Uani 1 1 d . . . . .
F5 F 0.7605(4) 0.3122(2) -0.02318(14) 0.0464(10) Uani 1 1 d . . . . .
F6 F 0.9347(3) 0.2843(2) 0.03997(15) 0.0423(9) Uani 1 1 d . . . . .
O1 O 0.6570(4) 0.0571(2) 0.45634(15) 0.0268(9) Uani 1 1 d . . . . .
O2 O 0.7642(4) -0.0547(2) 0.43072(17) 0.0310(10) Uani 1 1 d . . . . .
O21 O 0.7066(4) 0.4480(2) 0.04114(16) 0.0275(10) Uani 1 1 d . . . . .
O22 O 0.8033(4) 0.5620(2) 0.06760(16) 0.0285(10) Uani 1 1 d . . . . .
N8 N 0.8557(5) 0.0724(3) 0.1321(2) 0.0352(13) Uani 1 1 d . . . . .
N28 N 0.7943(5) 0.4378(3) 0.3724(2) 0.0316(13) Uani 1 1 d . . . . .
C2 C 0.7580(6) 0.0115(4) 0.4278(2) 0.0250(14) Uani 1 1 d . . . . .
C3 C 0.8406(6) 0.0758(3) 0.3971(2) 0.0235(13) Uani 1 1 d . . . . .
H3 H 0.9395 0.0818 0.4149 0.028 Uiso 1 1 calc R U . . .
C4 C 0.7264(5) 0.1256(3) 0.4319(2) 0.0226(13) Uani 1 1 d . . . . .
C5 C 0.8436(6) 0.0744(3) 0.3272(2) 0.0190(12) Uani 1 1 d . . . . .
C6 C 0.7309(5) 0.0443(3) 0.2926(2) 0.0231(13) Uani 1 1 d . . . . .
H6 H 0.6494 0.0243 0.3134 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7346(6) 0.0429(3) 0.2284(2) 0.0273(14) Uani 1 1 d . . . . .
H7 H 0.6569 0.0211 0.2061 0.033 Uiso 1 1 calc R U . . .
C8 C 0.8525(6) 0.0734(3) 0.1961(2) 0.0249(13) Uani 1 1 d . . . . .
C9 C 0.9657(6) 0.1047(3) 0.2312(2) 0.0261(14) Uani 1 1 d . . . . .
H9 H 1.0465 0.1262 0.2108 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9595(5) 0.1044(3) 0.2953(2) 0.0236(13) Uani 1 1 d . . . . .
H10 H 1.0373 0.1254 0.3181 0.028 Uiso 1 1 calc R U . . .
C11 C 0.6272(5) 0.1750(3) 0.3958(2) 0.0237(13) Uani 1 1 d . . . . .
C12 C 0.6819(6) 0.2297(3) 0.3562(2) 0.0242(13) Uani 1 1 d . . . . .
H12 H 0.7833 0.2332 0.3503 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5918(6) 0.2793(3) 0.3254(2) 0.0265(14) Uani 1 1 d . . . . .
H13 H 0.6307 0.3167 0.2990 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4434(6) 0.2731(3) 0.3338(3) 0.0271(14) Uani 1 1 d . . . . .
C15 C 0.3853(6) 0.2177(3) 0.3716(2) 0.0301(15) Uani 1 1 d . . . . .
H15 H 0.2837 0.2132 0.3761 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4769(5) 0.1690(3) 0.4024(2) 0.0272(14) Uani 1 1 d . . . . .
H16 H 0.4376 0.1312 0.4283 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7907(6) 0.1664(4) 0.4875(2) 0.0295(14) Uani 1 1 d . . . . .
C18 C 0.7305(6) 0.0478(4) 0.0968(3) 0.0423(18) Uani 1 1 d . . . . .
H18A H 0.7520 0.0508 0.0524 0.051 Uiso 1 1 calc R U . . .
H18B H 0.7072 -0.0040 0.1077 0.051 Uiso 1 1 calc R U . . .
H18C H 0.6479 0.0801 0.1063 0.051 Uiso 1 1 calc R U . . .
C19 C 0.9785(6) 0.1037(4) 0.0989(3) 0.0389(17) Uani 1 1 d . . . . .
H19A H 0.9631 0.0984 0.0542 0.047 Uiso 1 1 calc R U . . .
H19B H 0.9885 0.1568 0.1093 0.047 Uiso 1 1 calc R U . . .
H19C H 1.0665 0.0770 0.1108 0.047 Uiso 1 1 calc R U . . .
C22 C 0.7978(6) 0.4953(4) 0.0727(2) 0.0252(14) Uani 1 1 d . . . . .
C23 C 0.8745(6) 0.4342(3) 0.1097(2) 0.0221(13) Uani 1 1 d . . . . .
H23 H 0.9782 0.4292 0.0976 0.027 Uiso 1 1 calc R U . . .
C24 C 0.7740(6) 0.3812(3) 0.0704(2) 0.0247(13) Uani 1 1 d . . . . .
C25 C 0.8554(5) 0.4368(3) 0.1788(2) 0.0192(12) Uani 1 1 d . . . . .
C26 C 0.7302(5) 0.4663(3) 0.2054(2) 0.0225(13) Uani 1 1 d . . . . .
H26 H 0.6577 0.4865 0.1791 0.027 Uiso 1 1 calc R U . . .
C27 C 0.7087(5) 0.4670(3) 0.2686(2) 0.0240(13) Uani 1 1 d . . . . .
H27 H 0.6224 0.4875 0.2851 0.029 Uiso 1 1 calc R U . . .
C28 C 0.8146(5) 0.4373(3) 0.3089(2) 0.0238(13) Uani 1 1 d . . . . .
C29 C 0.9408(6) 0.4086(3) 0.2821(2) 0.0270(14) Uani 1 1 d . . . . .
H29 H 1.0149 0.3892 0.3079 0.032 Uiso 1 1 calc R U . . .
C30 C 0.9586(6) 0.4081(3) 0.2185(2) 0.0251(14) Uani 1 1 d . . . . .
H30 H 1.0443 0.3875 0.2016 0.030 Uiso 1 1 calc R U . . .
C31 C 0.6681(6) 0.3318(3) 0.1028(2) 0.0237(12) Uani 1 1 d . . . . .
C32 C 0.5192(5) 0.3388(3) 0.0930(2) 0.0279(13) Uani 1 1 d . . . . .
H32 H 0.4838 0.3772 0.0666 0.033 Uiso 1 1 calc R U . . .
C33 C 0.4235(6) 0.2904(3) 0.1215(2) 0.0288(15) Uani 1 1 d . . . . .
H33 H 0.3226 0.2954 0.1149 0.035 Uiso 1 1 calc R U . . .
C34 C 0.4766(6) 0.2346(3) 0.1597(2) 0.0289(14) Uani 1 1 d . . . . .
C35 C 0.6233(6) 0.2271(3) 0.1719(2) 0.0263(14) Uani 1 1 d . . . . .
H35 H 0.6576 0.1893 0.1990 0.032 Uiso 1 1 calc R U . . .
C36 C 0.7178(6) 0.2762(3) 0.1435(2) 0.0275(14) Uani 1 1 d . . . . .
H36 H 0.8182 0.2723 0.1517 0.033 Uiso 1 1 calc R U . . .
C37 C 0.8523(6) 0.3401(4) 0.0179(2) 0.0329(14) Uani 1 1 d . . . . .
C38 C 0.6573(6) 0.4608(3) 0.3989(2) 0.0356(15) Uani 1 1 d . . . . .
H38A H 0.6626 0.4576 0.4442 0.043 Uiso 1 1 calc R U . . .
H38B H 0.6363 0.5124 0.3867 0.043 Uiso 1 1 calc R U . . .
H38C H 0.5805 0.4278 0.3839 0.043 Uiso 1 1 calc R U . . .
C39 C 0.9055(6) 0.4073(4) 0.4130(3) 0.0379(17) Uani 1 1 d . . . . .
H39A H 0.8743 0.4119 0.4562 0.045 Uiso 1 1 calc R U . . .
H39B H 0.9211 0.3544 0.4031 0.045 Uiso 1 1 calc R U . . .
H39C H 0.9956 0.4350 0.4071 0.045 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br14 C14 1.894(5) . ?
Br34 C34 1.906(5) . ?
F1 C17 1.349(6) . ?
F2 C17 1.341(6) . ?
F3 C17 1.348(6) . ?
F4 C37 1.351(6) . ?
F5 C37 1.326(6) . ?
F6 C37 1.343(6) . ?
O1 C2 1.387(6) . ?
O1 C4 1.481(6) . ?
O2 C2 1.187(6) . ?
O21 C22 1.377(6) . ?
O21 C24 1.489(6) . ?
O22 C22 1.198(6) . ?
N8 C8 1.381(6) . ?
N8 C19 1.458(7) . ?
N8 C18 1.458(7) . ?
N28 C28 1.383(6) . ?
N28 C38 1.453(7) . ?
N28 C39 1.459(7) . ?
C2 C3 1.533(8) . ?
C3 C5 1.508(7) . ?
C3 C4 1.574(7) . ?
C3 H3 1.0000 . ?
C4 C11 1.495(7) . ?
C4 C17 1.527(7) . ?
C5 C10 1.384(7) . ?
C5 C6 1.393(7) . ?
C6 C7 1.385(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(7) . ?
C9 C10 1.385(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.395(7) . ?
C11 C16 1.404(7) . ?
C12 C13 1.388(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(8) . ?
C15 C16 1.387(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 C23 1.529(8) . ?
C23 C25 1.504(7) . ?
C23 C24 1.577(7) . ?
C23 H23 1.0000 . ?
C24 C31 1.493(7) . ?
C24 C37 1.534(7) . ?
C25 C30 1.382(7) . ?
C25 C26 1.399(7) . ?
C26 C27 1.378(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.416(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.403(7) . ?
C29 C30 1.382(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.402(7) . ?
C31 C36 1.405(7) . ?
C32 C33 1.384(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.391(7) . ?
C35 C36 1.384(7) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 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
C2 O1 C4 92.0(4) . . ?
C22 O21 C24 91.5(4) . . ?
C8 N8 C19 120.3(5) . . ?
C8 N8 C18 120.7(5) . . ?
C19 N8 C18 118.7(4) . . ?
C28 N28 C38 120.8(4) . . ?
C28 N28 C39 119.8(4) . . ?
C38 N28 C39 119.0(4) . . ?
O2 C2 O1 126.6(5) . . ?
O2 C2 C3 138.4(5) . . ?
O1 C2 C3 95.0(5) . . ?
C5 C3 C2 115.5(4) . . ?
C5 C3 C4 119.9(4) . . ?
C2 C3 C4 83.2(4) . . ?
C5 C3 H3 111.8 . . ?
C2 C3 H3 111.8 . . ?
C4 C3 H3 111.8 . . ?
O1 C4 C11 114.0(4) . . ?
O1 C4 C17 106.5(4) . . ?
C11 C4 C17 111.6(5) . . ?
O1 C4 C3 89.7(4) . . ?
C11 C4 C3 120.0(4) . . ?
C17 C4 C3 112.6(4) . . ?
C10 C5 C6 117.6(5) . . ?
C10 C5 C3 120.4(5) . . ?
C6 C5 C3 122.0(5) . . ?
C7 C6 C5 121.7(5) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
N8 C8 C7 120.5(5) . . ?
N8 C8 C9 121.8(5) . . ?
C7 C8 C9 117.7(5) . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C5 C10 C9 122.1(5) . . ?
C5 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C16 118.5(5) . . ?
C12 C11 C4 120.7(5) . . ?
C16 C11 C4 120.8(5) . . ?
C13 C12 C11 121.5(5) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 118.8(5) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 121.0(5) . . ?
C13 C14 Br14 118.9(4) . . ?
C15 C14 Br14 120.0(4) . . ?
C16 C15 C14 119.4(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 120.7(5) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
F2 C17 F3 107.7(5) . . ?
F2 C17 F1 106.7(4) . . ?
F3 C17 F1 106.8(4) . . ?
F2 C17 C4 111.6(4) . . ?
F3 C17 C4 111.7(4) . . ?
F1 C17 C4 112.1(5) . . ?
N8 C18 H18A 109.5 . . ?
N8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O22 C22 O21 126.4(5) . . ?
O22 C22 C23 137.7(5) . . ?
O21 C22 C23 95.9(5) . . ?
C25 C23 C22 116.2(4) . . ?
C25 C23 C24 118.9(4) . . ?
C22 C23 C24 82.8(4) . . ?
C25 C23 H23 112.0 . . ?
C22 C23 H23 112.0 . . ?
C24 C23 H23 112.0 . . ?
O21 C24 C31 113.4(4) . . ?
O21 C24 C37 105.6(4) . . ?
C31 C24 C37 111.9(5) . . ?
O21 C24 C23 89.6(4) . . ?
C31 C24 C23 119.5(4) . . ?
C37 C24 C23 113.9(4) . . ?
C30 C25 C26 117.4(5) . . ?
C30 C25 C23 121.5(5) . . ?
C26 C25 C23 121.1(5) . . ?
C27 C26 C25 122.0(5) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C26 C27 C28 120.4(5) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
N28 C28 C29 121.7(5) . . ?
N28 C28 C27 120.9(5) . . ?
C29 C28 C27 117.5(5) . . ?
C30 C29 C28 120.8(5) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C25 C30 C29 122.1(5) . . ?
C25 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
C32 C31 C36 118.7(5) . . ?
C32 C31 C24 121.5(5) . . ?
C36 C31 C24 119.7(5) . . ?
C33 C32 C31 120.5(5) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 119.2(5) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C33 C34 C35 121.9(5) . . ?
C33 C34 Br34 120.3(4) . . ?
C35 C34 Br34 117.8(5) . . ?
C36 C35 C34 118.3(5) . . ?
C36 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
C35 C36 C31 121.2(5) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
F5 C37 F6 108.9(5) . . ?
F5 C37 F4 107.3(4) . . ?
F6 C37 F4 106.4(4) . . ?
F5 C37 C24 111.7(5) . . ?
F6 C37 C24 111.3(4) . . ?
F4 C37 C24 111.1(5) . . ?
N28 C38 H38A 109.5 . . ?
N28 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N28 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N28 C39 H39A 109.5 . . ?
N28 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N28 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 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
C4 O1 C2 O2 178.3(6) . . . . ?
C4 O1 C2 C3 -1.6(4) . . . . ?
O2 C2 C3 C5 61.6(9) . . . . ?
O1 C2 C3 C5 -118.4(5) . . . . ?
O2 C2 C3 C4 -178.4(7) . . . . ?
O1 C2 C3 C4 1.5(4) . . . . ?
C2 O1 C4 C11 124.6(4) . . . . ?
C2 O1 C4 C17 -111.9(4) . . . . ?
C2 O1 C4 C3 1.6(4) . . . . ?
C5 C3 C4 O1 114.1(5) . . . . ?
C2 C3 C4 O1 -1.4(3) . . . . ?
C5 C3 C4 C11 -3.8(7) . . . . ?
C2 C3 C4 C11 -119.3(5) . . . . ?
C5 C3 C4 C17 -138.1(5) . . . . ?
C2 C3 C4 C17 106.4(5) . . . . ?
C2 C3 C5 C10 -150.2(5) . . . . ?
C4 C3 C5 C10 112.7(6) . . . . ?
C2 C3 C5 C6 30.6(7) . . . . ?
C4 C3 C5 C6 -66.5(7) . . . . ?
C10 C5 C6 C7 1.2(8) . . . . ?
C3 C5 C6 C7 -179.6(5) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C19 N8 C8 C7 -179.7(5) . . . . ?
C18 N8 C8 C7 7.1(8) . . . . ?
C19 N8 C8 C9 0.5(8) . . . . ?
C18 N8 C8 C9 -172.7(5) . . . . ?
C6 C7 C8 N8 -179.5(5) . . . . ?
C6 C7 C8 C9 0.3(8) . . . . ?
N8 C8 C9 C10 -179.6(5) . . . . ?
C7 C8 C9 C10 0.6(8) . . . . ?
C6 C5 C10 C9 -0.3(8) . . . . ?
C3 C5 C10 C9 -179.5(5) . . . . ?
C8 C9 C10 C5 -0.6(8) . . . . ?
O1 C4 C11 C12 -162.5(4) . . . . ?
C17 C4 C11 C12 76.7(6) . . . . ?
C3 C4 C11 C12 -58.0(7) . . . . ?
O1 C4 C11 C16 19.5(7) . . . . ?
C17 C4 C11 C16 -101.2(6) . . . . ?
C3 C4 C11 C16 124.1(5) . . . . ?
C16 C11 C12 C13 2.2(8) . . . . ?
C4 C11 C12 C13 -175.8(5) . . . . ?
C11 C12 C13 C14 -0.9(8) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C12 C13 C14 Br14 177.2(4) . . . . ?
C13 C14 C15 C16 1.6(8) . . . . ?
Br14 C14 C15 C16 -176.6(4) . . . . ?
C14 C15 C16 C11 -0.2(8) . . . . ?
C12 C11 C16 C15 -1.6(8) . . . . ?
C4 C11 C16 C15 176.3(5) . . . . ?
O1 C4 C17 F2 -68.1(6) . . . . ?
C11 C4 C17 F2 56.9(6) . . . . ?
C3 C4 C17 F2 -164.8(4) . . . . ?
O1 C4 C17 F3 171.3(4) . . . . ?
C11 C4 C17 F3 -63.6(6) . . . . ?
C3 C4 C17 F3 74.6(6) . . . . ?
O1 C4 C17 F1 51.6(5) . . . . ?
C11 C4 C17 F1 176.6(4) . . . . ?
C3 C4 C17 F1 -45.2(6) . . . . ?
C24 O21 C22 O22 176.9(6) . . . . ?
C24 O21 C22 C23 -2.8(4) . . . . ?
O22 C22 C23 C25 64.3(9) . . . . ?
O21 C22 C23 C25 -116.1(5) . . . . ?
O22 C22 C23 C24 -177.0(7) . . . . ?
O21 C22 C23 C24 2.7(4) . . . . ?
C22 O21 C24 C31 124.9(4) . . . . ?
C22 O21 C24 C37 -112.1(4) . . . . ?
C22 O21 C24 C23 2.7(4) . . . . ?
C25 C23 C24 O21 113.6(5) . . . . ?
C22 C23 C24 O21 -2.4(3) . . . . ?
C25 C23 C24 C31 -3.3(7) . . . . ?
C22 C23 C24 C31 -119.4(5) . . . . ?
C25 C23 C24 C37 -139.4(5) . . . . ?
C22 C23 C24 C37 104.5(5) . . . . ?
C22 C23 C25 C30 -152.6(5) . . . . ?
C24 C23 C25 C30 110.9(6) . . . . ?
C22 C23 C25 C26 29.4(7) . . . . ?
C24 C23 C25 C26 -67.1(7) . . . . ?
C30 C25 C26 C27 -0.2(8) . . . . ?
C23 C25 C26 C27 177.9(5) . . . . ?
C25 C26 C27 C28 0.0(8) . . . . ?
C38 N28 C28 C29 -173.7(5) . . . . ?
C39 N28 C28 C29 -0.5(8) . . . . ?
C38 N28 C28 C27 7.2(8) . . . . ?
C39 N28 C28 C27 -179.6(5) . . . . ?
C26 C27 C28 N28 179.9(5) . . . . ?
C26 C27 C28 C29 0.8(8) . . . . ?
N28 C28 C29 C30 179.5(5) . . . . ?
C27 C28 C29 C30 -1.3(8) . . . . ?
C26 C25 C30 C29 -0.4(8) . . . . ?
C23 C25 C30 C29 -178.4(5) . . . . ?
C28 C29 C30 C25 1.2(9) . . . . ?
O21 C24 C31 C32 14.6(7) . . . . ?
C37 C24 C31 C32 -104.8(6) . . . . ?
C23 C24 C31 C32 118.3(5) . . . . ?
O21 C24 C31 C36 -166.2(4) . . . . ?
C37 C24 C31 C36 74.3(6) . . . . ?
C23 C24 C31 C36 -62.6(7) . . . . ?
C36 C31 C32 C33 -1.9(8) . . . . ?
C24 C31 C32 C33 177.2(5) . . . . ?
C31 C32 C33 C34 -0.2(8) . . . . ?
C32 C33 C34 C35 2.0(8) . . . . ?
C32 C33 C34 Br34 -176.5(4) . . . . ?
C33 C34 C35 C36 -1.6(8) . . . . ?
Br34 C34 C35 C36 177.1(4) . . . . ?
C34 C35 C36 C31 -0.7(8) . . . . ?
C32 C31 C36 C35 2.4(8) . . . . ?
C24 C31 C36 C35 -176.8(5) . . . . ?
O21 C24 C37 F5 -66.9(6) . . . . ?
C31 C24 C37 F5 57.0(6) . . . . ?
C23 C24 C37 F5 -163.5(4) . . . . ?
O21 C24 C37 F6 171.2(4) . . . . ?
C31 C24 C37 F6 -64.9(6) . . . . ?
C23 C24 C37 F6 74.6(6) . . . . ?
O21 C24 C37 F4 52.9(6) . . . . ?
C31 C24 C37 F4 176.9(4) . . . . ?
C23 C24 C37 F4 -43.7(6) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_60
_database_code_depnum_ccdc_archive 'CCDC 1886143'
loop_
_audit_author_name
_audit_author_address
'ALEXANDRA MARTHA ZOYA Slawin' 'University of St Andrews'
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_audit_creation_date             2015-10-14
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C26 H19 Br F9 N O2'
_chemical_formula_moiety         'C26 H19 Br F9 N O2'
_chemical_formula_weight         628.33
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.6483(15)
_cell_length_b                   16.5846(18)
_cell_length_c                   23.807(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5388.8(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12485
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2512.00
_exptl_absorpt_coefficient_mu    1.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_T_max  0.953

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            23697
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_theta_max         25.399
_diffrn_reflns_theta_min         2.113
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             9651
_reflns_number_gt                6829
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0719
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         9651
_refine_ls_number_parameters     719
_refine_ls_goodness_of_fit_ref   0.861
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2281 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br19 Br -0.15962(5) 0.23088(4) 0.16814(3) 0.0459(2) Uani 1 1 d . . . . .
Br49 Br 0.50556(4) 0.57579(4) -0.14056(3) 0.03945(17) Uani 1 1 d . . . . .
F1 F 0.3662(2) 0.2843(2) 0.44099(14) 0.0482(10) Uani 1 1 d . . . . .
F2 F 0.2919(2) 0.3086(2) 0.51865(14) 0.0475(10) Uani 1 1 d . . . . .
F3 F 0.3289(3) 0.1862(2) 0.49615(16) 0.0572(11) Uani 1 1 d . . . . .
F4 F 0.1336(2) 0.2295(2) 0.48881(13) 0.0398(9) Uani 1 1 d . . . . .
F5 F 0.1742(2) 0.32191(19) 0.42755(13) 0.0394(9) Uani 1 1 d . . . . .
F6 F 0.1945(2) 0.11116(19) 0.42513(13) 0.0369(9) Uani 1 1 d . . . . .
F7 F 0.0895(2) 0.1919(2) 0.38444(13) 0.0401(9) Uani 1 1 d . . . . .
F8 F 0.3415(2) 0.16361(17) 0.36694(12) 0.0293(7) Uani 1 1 d . . . . .
F9 F 0.2632(2) 0.26947(18) 0.33572(13) 0.0294(7) Uani 1 1 d . . . . .
F31 F 0.0534(3) 0.5757(3) 0.06305(19) 0.0788(14) Uani 1 1 d . . . . .
F32 F 0.0174(3) 0.4536(3) 0.03766(15) 0.0621(12) Uani 1 1 d . . . . .
F33 F -0.0385(2) 0.5024(2) 0.11530(15) 0.0513(10) Uani 1 1 d . . . . .
F34 F 0.1005(2) 0.3975(2) 0.13594(16) 0.0518(10) Uani 1 1 d . . . . .
F35 F 0.1471(2) 0.5205(2) 0.15501(15) 0.0528(10) Uani 1 1 d . . . . .
F36 F 0.2337(2) 0.5202(2) 0.04364(14) 0.0408(9) Uani 1 1 d . . . . .
F37 F 0.2054(2) 0.3909(2) 0.04369(15) 0.0425(9) Uani 1 1 d . . . . .
F38 F 0.3414(2) 0.51743(17) 0.13218(12) 0.0310(8) Uani 1 1 d . . . . .
F39 F 0.2898(2) 0.39879(18) 0.15924(13) 0.0317(8) Uani 1 1 d . . . . .
O5 O 0.2155(3) 0.0584(2) 0.31218(15) 0.0241(9) Uani 1 1 d D . . . .
O7 O 0.4063(3) 0.0468(2) 0.28852(15) 0.0247(9) Uani 1 1 d . . . . .
O35 O 0.3789(3) 0.3200(2) 0.07285(16) 0.0255(9) Uani 1 1 d D . . . .
O37 O 0.4472(3) 0.2881(2) 0.17862(15) 0.0259(9) Uani 1 1 d . . . . .
N8 N 0.4817(3) 0.1539(3) 0.24722(19) 0.0226(11) Uani 1 1 d D . . . .
N38 N 0.4979(3) 0.3995(3) 0.22687(18) 0.0227(10) Uani 1 1 d D . . . .
C1 C 0.2980(4) 0.2565(4) 0.4763(3) 0.0351(15) Uani 1 1 d . . . . .
C2 C 0.1984(4) 0.2489(4) 0.4472(2) 0.0310(15) Uani 1 1 d . . . . .
C3 C 0.1833(4) 0.1846(3) 0.4004(2) 0.0284(14) Uani 1 1 d . . . . .
C4 C 0.2514(4) 0.1893(3) 0.3487(2) 0.0267(14) Uani 1 1 d . . . . .
C5 C 0.2224(4) 0.1402(3) 0.2955(2) 0.0226(13) Uani 1 1 d . . . . .
C6 C 0.3039(4) 0.1526(3) 0.2491(2) 0.0217(13) Uani 1 1 d . . . . .
H6 H 0.3147 0.2120 0.2450 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4025(4) 0.1145(3) 0.2643(2) 0.0233(14) Uani 1 1 d . . . . .
C9 C 0.5803(4) 0.1205(3) 0.2511(2) 0.0251(14) Uani 1 1 d . . . . .
H9A H 0.5842 0.0857 0.2848 0.030 Uiso 1 1 calc R U . . .
H9B H 0.6275 0.1652 0.2562 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6107(4) 0.0714(3) 0.2000(2) 0.0258(13) Uani 1 1 d . . . . .
C11 C 0.6949(4) 0.0243(3) 0.2043(3) 0.0350(15) Uani 1 1 d . . . . .
H11 H 0.7295 0.0220 0.2389 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7286(5) -0.0194(4) 0.1583(3) 0.0475(19) Uani 1 1 d . . . . .
H12 H 0.7860 -0.0516 0.1615 0.057 Uiso 1 1 calc R U . . .
C13 C 0.6779(6) -0.0157(4) 0.1077(3) 0.056(2) Uani 1 1 d . . . . .
H13 H 0.7009 -0.0448 0.0759 0.068 Uiso 1 1 calc R U . . .
C14 C 0.5942(6) 0.0303(4) 0.1040(3) 0.056(2) Uani 1 1 d . . . . .
H14 H 0.5596 0.0325 0.0694 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5595(5) 0.0736(4) 0.1498(2) 0.0398(16) Uani 1 1 d . . . . .
H15 H 0.5011 0.1045 0.1467 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1231(4) 0.1661(3) 0.2703(2) 0.0241(14) Uani 1 1 d . . . . .
C17 C 0.0547(4) 0.1077(4) 0.2575(2) 0.0289(15) Uani 1 1 d . . . . .
H17 H 0.0668 0.0534 0.2683 0.035 Uiso 1 1 calc R U . . .
C18 C -0.0319(4) 0.1261(4) 0.2288(2) 0.0326(15) Uani 1 1 d . . . . .
H18 H -0.0785 0.0853 0.2204 0.039 Uiso 1 1 calc R U . . .
C19 C -0.0482(4) 0.2058(4) 0.2128(2) 0.0315(15) Uani 1 1 d . . . . .
C20 C 0.0175(4) 0.2662(4) 0.2263(2) 0.0323(14) Uani 1 1 d . . . . .
H20 H 0.0043 0.3205 0.2162 0.039 Uiso 1 1 calc R U . . .
C21 C 0.1043(4) 0.2464(4) 0.2552(2) 0.0297(14) Uani 1 1 d . . . . .
H21 H 0.1501 0.2875 0.2644 0.036 Uiso 1 1 calc R U . . .
C22 C 0.2732(4) 0.1202(3) 0.1916(2) 0.0245(14) Uani 1 1 d . . . . .
C23 C 0.2420(4) 0.1734(4) 0.1499(2) 0.0303(15) Uani 1 1 d . . . . .
H23 H 0.2402 0.2296 0.1576 0.036 Uiso 1 1 calc R U . . .
C24 C 0.2136(4) 0.1455(4) 0.0974(3) 0.0389(17) Uani 1 1 d . . . . .
H24 H 0.1919 0.1824 0.0696 0.047 Uiso 1 1 calc R U . . .
C25 C 0.2168(5) 0.0637(4) 0.0858(2) 0.0413(18) Uani 1 1 d . . . . .
H25 H 0.1969 0.0445 0.0500 0.050 Uiso 1 1 calc R U . . .
C26 C 0.2488(4) 0.0104(4) 0.1259(3) 0.0376(16) Uani 1 1 d . . . . .
H26 H 0.2527 -0.0455 0.1174 0.045 Uiso 1 1 calc R U . . .
C27 C 0.2759(4) 0.0378(4) 0.1795(2) 0.0316(15) Uani 1 1 d . . . . .
H27 H 0.2960 0.0004 0.2075 0.038 Uiso 1 1 calc R U . . .
C31 C 0.0383(5) 0.5001(5) 0.0814(3) 0.0476(19) Uani 1 1 d . . . . .
C32 C 0.1280(4) 0.4691(4) 0.1124(3) 0.0332(15) Uani 1 1 d . . . . .
C33 C 0.2208(4) 0.4546(4) 0.0773(3) 0.0294(14) Uani 1 1 d . . . . .
C34 C 0.3165(4) 0.4428(3) 0.1126(2) 0.0237(13) Uani 1 1 d . . . . .
C35 C 0.4056(4) 0.4014(3) 0.0839(2) 0.0222(13) Uani 1 1 d . . . . .
C36 C 0.4961(4) 0.4053(3) 0.1248(2) 0.0216(12) Uani 1 1 d . . . . .
H36 H 0.5067 0.4632 0.1347 0.026 Uiso 1 1 calc R U . . .
C37 C 0.4785(4) 0.3596(3) 0.1797(2) 0.0235(13) Uani 1 1 d . . . . .
C39 C 0.4874(4) 0.3642(3) 0.2830(2) 0.0240(13) Uani 1 1 d . . . . .
H39A H 0.4330 0.3248 0.2823 0.029 Uiso 1 1 calc R U . . .
H39B H 0.4693 0.4075 0.3097 0.029 Uiso 1 1 calc R U . . .
C40 C 0.5794(4) 0.3220(3) 0.3047(2) 0.0238(13) Uani 1 1 d . . . . .
C41 C 0.5713(4) 0.2732(3) 0.3521(2) 0.0274(13) Uani 1 1 d . . . . .
H41 H 0.5091 0.2661 0.3694 0.033 Uiso 1 1 calc R U . . .
C42 C 0.6521(4) 0.2350(4) 0.3742(2) 0.0350(15) Uani 1 1 d . . . . .
H42 H 0.6450 0.2008 0.4060 0.042 Uiso 1 1 calc R U . . .
C43 C 0.7444(4) 0.2463(4) 0.3503(2) 0.0366(16) Uani 1 1 d . . . . .
H43 H 0.8003 0.2207 0.3661 0.044 Uiso 1 1 calc R U . . .
C44 C 0.7536(4) 0.2953(4) 0.3033(3) 0.0326(15) Uani 1 1 d . . . . .
H44 H 0.8163 0.3036 0.2869 0.039 Uiso 1 1 calc R U . . .
C45 C 0.6709(4) 0.3324(3) 0.2801(2) 0.0272(14) Uani 1 1 d . . . . .
H45 H 0.6773 0.3648 0.2474 0.033 Uiso 1 1 calc R U . . .
C46 C 0.4307(4) 0.4435(3) 0.0287(2) 0.0212(13) Uani 1 1 d . . . . .
C47 C 0.4223(4) 0.4038(3) -0.0224(2) 0.0277(14) Uani 1 1 d . . . . .
H47 H 0.4009 0.3493 -0.0229 0.033 Uiso 1 1 calc R U . . .
C48 C 0.4446(4) 0.4418(4) -0.0729(2) 0.0321(15) Uani 1 1 d . . . . .
H48 H 0.4383 0.4137 -0.1075 0.039 Uiso 1 1 calc R U . . .
C49 C 0.4761(4) 0.5216(3) -0.0721(2) 0.0259(14) Uani 1 1 d . . . . .
C50 C 0.4849(4) 0.5626(3) -0.0215(2) 0.0278(13) Uani 1 1 d . . . . .
H50 H 0.5061 0.6172 -0.0212 0.033 Uiso 1 1 calc R U . . .
C51 C 0.4629(4) 0.5239(3) 0.0284(2) 0.0257(14) Uani 1 1 d . . . . .
H51 H 0.4697 0.5521 0.0629 0.031 Uiso 1 1 calc R U . . .
C52 C 0.5909(4) 0.3744(3) 0.0973(2) 0.0240(14) Uani 1 1 d . . . . .
C53 C 0.6662(4) 0.4286(4) 0.0870(2) 0.0265(13) Uani 1 1 d . . . . .
H53 H 0.6588 0.4835 0.0976 0.032 Uiso 1 1 calc R U . . .
C54 C 0.7520(4) 0.4033(4) 0.0614(2) 0.0341(16) Uani 1 1 d . . . . .
H54 H 0.8027 0.4412 0.0542 0.041 Uiso 1 1 calc R U . . .
C55 C 0.7646(4) 0.3235(4) 0.0462(2) 0.0350(16) Uani 1 1 d . . . . .
H55 H 0.8233 0.3065 0.0283 0.042 Uiso 1 1 calc R U . . .
C56 C 0.6903(4) 0.2683(4) 0.0574(2) 0.0325(15) Uani 1 1 d . . . . .
H56 H 0.6989 0.2132 0.0476 0.039 Uiso 1 1 calc R U . . .
C57 C 0.6035(4) 0.2930(3) 0.0827(2) 0.0286(14) Uani 1 1 d . . . . .
H57 H 0.5530 0.2551 0.0902 0.034 Uiso 1 1 calc R U . . .
H5 H 0.281(2) 0.035(4) 0.312(3) 0.09(3) Uiso 1 1 d D . . . .
H8 H 0.472(4) 0.2042(18) 0.227(2) 0.050(19) Uiso 1 1 d D . . . .
H35 H 0.392(6) 0.293(4) 0.1086(17) 0.12(3) Uiso 1 1 d D . . . .
H38 H 0.518(4) 0.4554(12) 0.220(2) 0.06(2) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br19 C19 1.902(6) . ?
Br49 C49 1.904(5) . ?
F1 C1 1.336(6) . ?
F2 C1 1.331(6) . ?
F3 C1 1.326(7) . ?
F4 C2 1.367(6) . ?
F5 C2 1.339(6) . ?
F6 C3 1.361(6) . ?
F7 C3 1.342(6) . ?
F8 C4 1.371(6) . ?
F9 C4 1.375(6) . ?
F31 C31 1.343(8) . ?
F32 C31 1.326(8) . ?
F33 C31 1.323(7) . ?
F34 C32 1.366(7) . ?
F35 C32 1.352(6) . ?
F36 C33 1.362(6) . ?
F37 C33 1.341(6) . ?
F38 C34 1.366(6) . ?
F39 C34 1.377(6) . ?
O5 C5 1.416(6) . ?
O5 H5 0.979(7) . ?
O7 C7 1.263(6) . ?
O35 C35 1.423(6) . ?
O35 H35 0.979(7) . ?
O37 C37 1.260(6) . ?
N8 C7 1.327(7) . ?
N8 C9 1.458(6) . ?
N8 H8 0.978(7) . ?
N38 C37 1.330(6) . ?
N38 C39 1.466(6) . ?
N38 H38 0.979(7) . ?
C1 C2 1.530(8) . ?
C2 C3 1.556(8) . ?
C3 C4 1.544(7) . ?
C4 C5 1.558(7) . ?
C5 C16 1.542(7) . ?
C5 C6 1.582(7) . ?
C6 C22 1.529(7) . ?
C6 C7 1.530(7) . ?
C6 H6 1.0000 . ?
C9 C10 1.521(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.386(8) . ?
C10 C11 1.393(7) . ?
C11 C12 1.391(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.380(8) . ?
C16 C21 1.404(7) . ?
C17 C18 1.399(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(8) . ?
C20 C21 1.407(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.394(7) . ?
C22 C27 1.397(7) . ?
C23 C24 1.388(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.374(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.404(8) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C31 C32 1.520(9) . ?
C32 C33 1.535(8) . ?
C33 C34 1.566(7) . ?
C34 C35 1.554(7) . ?
C35 C46 1.528(7) . ?
C35 C36 1.575(7) . ?
C36 C37 1.529(7) . ?
C36 C52 1.539(7) . ?
C36 H36 1.0000 . ?
C39 C40 1.527(7) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C45 1.391(7) . ?
C40 C41 1.393(7) . ?
C41 C42 1.376(7) . ?
C41 H41 0.9500 . ?
C42 C43 1.394(8) . ?
C42 H42 0.9500 . ?
C43 C44 1.389(8) . ?
C43 H43 0.9500 . ?
C44 C45 1.400(7) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.388(7) . ?
C46 C51 1.404(7) . ?
C47 C48 1.392(7) . ?
C47 H47 0.9500 . ?
C48 C49 1.392(8) . ?
C48 H48 0.9500 . ?
C49 C50 1.388(7) . ?
C50 C51 1.383(7) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C53 1.386(7) . ?
C52 C57 1.403(7) . ?
C53 C54 1.385(8) . ?
C53 H53 0.9500 . ?
C54 C55 1.384(8) . ?
C54 H54 0.9500 . ?
C55 C56 1.391(8) . ?
C55 H55 0.9500 . ?
C56 C57 1.392(7) . ?
C56 H56 0.9500 . ?
C57 H57 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
C5 O5 H5 109(4) . . ?
C35 O35 H35 103(5) . . ?
C7 N8 C9 123.1(4) . . ?
C7 N8 H8 118(3) . . ?
C9 N8 H8 119(3) . . ?
C37 N38 C39 123.5(4) . . ?
C37 N38 H38 113(3) . . ?
C39 N38 H38 123(3) . . ?
F3 C1 F2 108.6(5) . . ?
F3 C1 F1 107.9(5) . . ?
F2 C1 F1 107.2(5) . . ?
F3 C1 C2 111.8(5) . . ?
F2 C1 C2 109.9(5) . . ?
F1 C1 C2 111.3(5) . . ?
F5 C2 F4 107.8(4) . . ?
F5 C2 C1 107.7(5) . . ?
F4 C2 C1 105.5(4) . . ?
F5 C2 C3 109.7(4) . . ?
F4 C2 C3 105.7(4) . . ?
C1 C2 C3 119.8(5) . . ?
F7 C3 F6 108.1(4) . . ?
F7 C3 C4 110.1(4) . . ?
F6 C3 C4 108.8(4) . . ?
F7 C3 C2 105.5(4) . . ?
F6 C3 C2 106.8(4) . . ?
C4 C3 C2 117.2(5) . . ?
F8 C4 F9 105.5(4) . . ?
F8 C4 C3 105.8(4) . . ?
F9 C4 C3 107.4(4) . . ?
F8 C4 C5 108.9(4) . . ?
F9 C4 C5 110.6(4) . . ?
C3 C4 C5 118.0(4) . . ?
O5 C5 C16 108.5(4) . . ?
O5 C5 C4 106.7(4) . . ?
C16 C5 C4 113.2(4) . . ?
O5 C5 C6 111.6(4) . . ?
C16 C5 C6 108.1(4) . . ?
C4 C5 C6 108.7(4) . . ?
C22 C6 C7 108.0(4) . . ?
C22 C6 C5 112.7(4) . . ?
C7 C6 C5 113.5(4) . . ?
C22 C6 H6 107.5 . . ?
C7 C6 H6 107.5 . . ?
C5 C6 H6 107.5 . . ?
O7 C7 N8 122.9(5) . . ?
O7 C7 C6 120.8(5) . . ?
N8 C7 C6 116.1(5) . . ?
N8 C9 C10 113.8(5) . . ?
N8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 119.7(5) . . ?
C15 C10 C9 122.6(5) . . ?
C11 C10 C9 117.7(5) . . ?
C12 C11 C10 120.4(6) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.7(6) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 119.5(7) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.3(7) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 119.4(6) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C21 119.1(5) . . ?
C17 C16 C5 119.0(5) . . ?
C21 C16 C5 121.6(5) . . ?
C16 C17 C18 121.7(6) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 118.4(6) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C20 C19 C18 121.4(5) . . ?
C20 C19 Br19 119.4(4) . . ?
C18 C19 Br19 119.2(5) . . ?
C19 C20 C21 119.4(5) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 120.0(5) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C27 118.8(5) . . ?
C23 C22 C6 119.8(5) . . ?
C27 C22 C6 121.4(5) . . ?
C24 C23 C22 121.0(6) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 119.9(6) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.1(6) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.5(6) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C22 C27 C26 119.8(6) . . ?
C22 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
F33 C31 F32 109.0(6) . . ?
F33 C31 F31 107.0(6) . . ?
F32 C31 F31 108.7(6) . . ?
F33 C31 C32 110.6(5) . . ?
F32 C31 C32 110.9(6) . . ?
F31 C31 C32 110.5(6) . . ?
F35 C32 F34 107.1(5) . . ?
F35 C32 C31 107.8(5) . . ?
F34 C32 C31 105.8(5) . . ?
F35 C32 C33 110.4(5) . . ?
F34 C32 C33 108.3(5) . . ?
C31 C32 C33 117.0(5) . . ?
F37 C33 F36 107.4(5) . . ?
F37 C33 C32 108.6(5) . . ?
F36 C33 C32 107.6(5) . . ?
F37 C33 C34 110.6(5) . . ?
F36 C33 C34 107.9(4) . . ?
C32 C33 C34 114.5(5) . . ?
F38 C34 F39 105.7(4) . . ?
F38 C34 C35 110.8(4) . . ?
F39 C34 C35 109.1(4) . . ?
F38 C34 C33 106.1(4) . . ?
F39 C34 C33 106.2(4) . . ?
C35 C34 C33 118.1(4) . . ?
O35 C35 C46 109.4(4) . . ?
O35 C35 C34 107.5(4) . . ?
C46 C35 C34 110.6(4) . . ?
O35 C35 C36 110.7(4) . . ?
C46 C35 C36 109.8(4) . . ?
C34 C35 C36 108.9(4) . . ?
C37 C36 C52 109.3(4) . . ?
C37 C36 C35 112.7(4) . . ?
C52 C36 C35 112.5(4) . . ?
C37 C36 H36 107.3 . . ?
C52 C36 H36 107.3 . . ?
C35 C36 H36 107.3 . . ?
O37 C37 N38 123.6(5) . . ?
O37 C37 C36 120.1(5) . . ?
N38 C37 C36 116.3(5) . . ?
N38 C39 C40 114.3(4) . . ?
N38 C39 H39A 108.7 . . ?
C40 C39 H39A 108.7 . . ?
N38 C39 H39B 108.7 . . ?
C40 C39 H39B 108.7 . . ?
H39A C39 H39B 107.6 . . ?
C45 C40 C41 119.0(5) . . ?
C45 C40 C39 122.6(5) . . ?
C41 C40 C39 118.4(5) . . ?
C42 C41 C40 120.9(5) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C43 120.4(5) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 119.3(5) . . ?
C44 C43 H43 120.4 . . ?
C42 C43 H43 120.4 . . ?
C43 C44 C45 120.1(5) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C40 C45 C44 120.3(5) . . ?
C40 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C47 C46 C51 118.2(5) . . ?
C47 C46 C35 121.2(5) . . ?
C51 C46 C35 120.6(5) . . ?
C46 C47 C48 121.6(5) . . ?
C46 C47 H47 119.2 . . ?
C48 C47 H47 119.2 . . ?
C47 C48 C49 119.1(5) . . ?
C47 C48 H48 120.5 . . ?
C49 C48 H48 120.5 . . ?
C50 C49 C48 120.3(5) . . ?
C50 C49 Br49 119.5(4) . . ?
C48 C49 Br49 120.1(4) . . ?
C51 C50 C49 119.9(5) . . ?
C51 C50 H50 120.0 . . ?
C49 C50 H50 120.0 . . ?
C50 C51 C46 120.9(5) . . ?
C50 C51 H51 119.6 . . ?
C46 C51 H51 119.6 . . ?
C53 C52 C57 119.3(5) . . ?
C53 C52 C36 118.9(5) . . ?
C57 C52 C36 121.9(5) . . ?
C54 C53 C52 120.5(6) . . ?
C54 C53 H53 119.7 . . ?
C52 C53 H53 119.7 . . ?
C55 C54 C53 120.6(6) . . ?
C55 C54 H54 119.7 . . ?
C53 C54 H54 119.7 . . ?
C54 C55 C56 119.3(6) . . ?
C54 C55 H55 120.4 . . ?
C56 C55 H55 120.4 . . ?
C57 C56 C55 120.6(6) . . ?
C57 C56 H56 119.7 . . ?
C55 C56 H56 119.7 . . ?
C56 C57 C52 119.7(6) . . ?
C56 C57 H57 120.2 . . ?
C52 C57 H57 120.2 . . ?

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
F3 C1 C2 F5 -178.7(5) . . . . ?
F2 C1 C2 F5 60.6(6) . . . . ?
F1 C1 C2 F5 -58.0(6) . . . . ?
F3 C1 C2 F4 66.3(6) . . . . ?
F2 C1 C2 F4 -54.4(6) . . . . ?
F1 C1 C2 F4 -173.0(5) . . . . ?
F3 C1 C2 C3 -52.6(7) . . . . ?
F2 C1 C2 C3 -173.3(5) . . . . ?
F1 C1 C2 C3 68.1(7) . . . . ?
F5 C2 C3 F7 -56.0(6) . . . . ?
F4 C2 C3 F7 60.0(5) . . . . ?
C1 C2 C3 F7 178.8(5) . . . . ?
F5 C2 C3 F6 -170.9(4) . . . . ?
F4 C2 C3 F6 -54.9(5) . . . . ?
C1 C2 C3 F6 63.9(6) . . . . ?
F5 C2 C3 C4 66.9(6) . . . . ?
F4 C2 C3 C4 -177.1(4) . . . . ?
C1 C2 C3 C4 -58.3(7) . . . . ?
F7 C3 C4 F8 -166.9(4) . . . . ?
F6 C3 C4 F8 -48.6(5) . . . . ?
C2 C3 C4 F8 72.6(6) . . . . ?
F7 C3 C4 F9 80.9(5) . . . . ?
F6 C3 C4 F9 -160.9(4) . . . . ?
C2 C3 C4 F9 -39.7(6) . . . . ?
F7 C3 C4 C5 -44.8(6) . . . . ?
F6 C3 C4 C5 73.4(6) . . . . ?
C2 C3 C4 C5 -165.3(5) . . . . ?
F8 C4 C5 O5 62.4(5) . . . . ?
F9 C4 C5 O5 177.8(4) . . . . ?
C3 C4 C5 O5 -58.1(6) . . . . ?
F8 C4 C5 C16 -178.3(4) . . . . ?
F9 C4 C5 C16 -62.8(6) . . . . ?
C3 C4 C5 C16 61.2(6) . . . . ?
F8 C4 C5 C6 -58.1(5) . . . . ?
F9 C4 C5 C6 57.3(5) . . . . ?
C3 C4 C5 C6 -178.6(4) . . . . ?
O5 C5 C6 C22 73.4(5) . . . . ?
C16 C5 C6 C22 -45.9(6) . . . . ?
C4 C5 C6 C22 -169.2(4) . . . . ?
O5 C5 C6 C7 -49.8(6) . . . . ?
C16 C5 C6 C7 -169.0(5) . . . . ?
C4 C5 C6 C7 67.7(5) . . . . ?
C9 N8 C7 O7 4.4(8) . . . . ?
C9 N8 C7 C6 -170.9(5) . . . . ?
C22 C6 C7 O7 -86.4(6) . . . . ?
C5 C6 C7 O7 39.3(7) . . . . ?
C22 C6 C7 N8 89.1(6) . . . . ?
C5 C6 C7 N8 -145.2(5) . . . . ?
C7 N8 C9 C10 88.8(6) . . . . ?
N8 C9 C10 C15 14.0(8) . . . . ?
N8 C9 C10 C11 -167.6(5) . . . . ?
C15 C10 C11 C12 1.0(9) . . . . ?
C9 C10 C11 C12 -177.4(5) . . . . ?
C10 C11 C12 C13 0.2(9) . . . . ?
C11 C12 C13 C14 -0.8(10) . . . . ?
C12 C13 C14 C15 0.3(11) . . . . ?
C11 C10 C15 C14 -1.5(9) . . . . ?
C9 C10 C15 C14 176.8(6) . . . . ?
C13 C14 C15 C10 0.9(10) . . . . ?
O5 C5 C16 C17 -12.8(7) . . . . ?
C4 C5 C16 C17 -131.1(5) . . . . ?
C6 C5 C16 C17 108.3(5) . . . . ?
O5 C5 C16 C21 173.5(5) . . . . ?
C4 C5 C16 C21 55.2(7) . . . . ?
C6 C5 C16 C21 -65.3(6) . . . . ?
C21 C16 C17 C18 1.2(8) . . . . ?
C5 C16 C17 C18 -172.6(5) . . . . ?
C16 C17 C18 C19 0.4(8) . . . . ?
C17 C18 C19 C20 -2.1(8) . . . . ?
C17 C18 C19 Br19 174.6(4) . . . . ?
C18 C19 C20 C21 2.2(8) . . . . ?
Br19 C19 C20 C21 -174.5(4) . . . . ?
C17 C16 C21 C20 -1.1(8) . . . . ?
C5 C16 C21 C20 172.5(5) . . . . ?
C19 C20 C21 C16 -0.5(8) . . . . ?
C7 C6 C22 C23 -131.4(5) . . . . ?
C5 C6 C22 C23 102.5(5) . . . . ?
C7 C6 C22 C27 48.4(7) . . . . ?
C5 C6 C22 C27 -77.8(6) . . . . ?
C27 C22 C23 C24 0.3(8) . . . . ?
C6 C22 C23 C24 -179.9(5) . . . . ?
C22 C23 C24 C25 -0.6(9) . . . . ?
C23 C24 C25 C26 -0.5(9) . . . . ?
C24 C25 C26 C27 1.8(9) . . . . ?
C23 C22 C27 C26 0.9(8) . . . . ?
C6 C22 C27 C26 -178.8(5) . . . . ?
C25 C26 C27 C22 -2.0(9) . . . . ?
F33 C31 C32 F35 -61.0(7) . . . . ?
F32 C31 C32 F35 177.9(5) . . . . ?
F31 C31 C32 F35 57.3(7) . . . . ?
F33 C31 C32 F34 53.3(7) . . . . ?
F32 C31 C32 F34 -67.8(6) . . . . ?
F31 C31 C32 F34 171.6(5) . . . . ?
F33 C31 C32 C33 173.9(5) . . . . ?
F32 C31 C32 C33 52.8(8) . . . . ?
F31 C31 C32 C33 -67.8(8) . . . . ?
F35 C32 C33 F37 166.6(5) . . . . ?
F34 C32 C33 F37 49.6(6) . . . . ?
C31 C32 C33 F37 -69.7(7) . . . . ?
F35 C32 C33 F36 -77.5(6) . . . . ?
F34 C32 C33 F36 165.6(4) . . . . ?
C31 C32 C33 F36 46.2(7) . . . . ?
F35 C32 C33 C34 42.4(7) . . . . ?
F34 C32 C33 C34 -74.5(6) . . . . ?
C31 C32 C33 C34 166.2(6) . . . . ?
F37 C33 C34 F38 162.7(4) . . . . ?
F36 C33 C34 F38 45.5(5) . . . . ?
C32 C33 C34 F38 -74.3(6) . . . . ?
F37 C33 C34 F39 -85.2(5) . . . . ?
F36 C33 C34 F39 157.7(4) . . . . ?
C32 C33 C34 F39 37.9(6) . . . . ?
F37 C33 C34 C35 37.7(7) . . . . ?
F36 C33 C34 C35 -79.5(6) . . . . ?
C32 C33 C34 C35 160.7(5) . . . . ?
F38 C34 C35 O35 170.8(4) . . . . ?
F39 C34 C35 O35 54.8(5) . . . . ?
C33 C34 C35 O35 -66.5(6) . . . . ?
F38 C34 C35 C46 -69.8(5) . . . . ?
F39 C34 C35 C46 174.1(4) . . . . ?
C33 C34 C35 C46 52.8(6) . . . . ?
F38 C34 C35 C36 50.9(5) . . . . ?
F39 C34 C35 C36 -65.1(5) . . . . ?
C33 C34 C35 C36 173.5(4) . . . . ?
O35 C35 C36 C37 -55.5(5) . . . . ?
C46 C35 C36 C37 -176.3(4) . . . . ?
C34 C35 C36 C37 62.4(5) . . . . ?
O35 C35 C36 C52 68.7(5) . . . . ?
C46 C35 C36 C52 -52.2(6) . . . . ?
C34 C35 C36 C52 -173.4(4) . . . . ?
C39 N38 C37 O37 1.6(8) . . . . ?
C39 N38 C37 C36 -178.5(4) . . . . ?
C52 C36 C37 O37 -75.6(6) . . . . ?
C35 C36 C37 O37 50.2(6) . . . . ?
C52 C36 C37 N38 104.5(5) . . . . ?
C35 C36 C37 N38 -129.6(5) . . . . ?
C37 N38 C39 C40 89.6(6) . . . . ?
N38 C39 C40 C45 14.6(7) . . . . ?
N38 C39 C40 C41 -167.4(5) . . . . ?
C45 C40 C41 C42 -0.5(8) . . . . ?
C39 C40 C41 C42 -178.6(5) . . . . ?
C40 C41 C42 C43 1.7(8) . . . . ?
C41 C42 C43 C44 -1.2(8) . . . . ?
C42 C43 C44 C45 -0.4(8) . . . . ?
C41 C40 C45 C44 -1.1(8) . . . . ?
C39 C40 C45 C44 176.9(5) . . . . ?
C43 C44 C45 C40 1.6(8) . . . . ?
O35 C35 C46 C47 2.4(7) . . . . ?
C34 C35 C46 C47 -115.8(5) . . . . ?
C36 C35 C46 C47 124.1(5) . . . . ?
O35 C35 C46 C51 -177.6(4) . . . . ?
C34 C35 C46 C51 64.2(6) . . . . ?
C36 C35 C46 C51 -56.0(6) . . . . ?
C51 C46 C47 C48 -0.3(8) . . . . ?
C35 C46 C47 C48 179.7(5) . . . . ?
C46 C47 C48 C49 0.1(8) . . . . ?
C47 C48 C49 C50 -0.2(8) . . . . ?
C47 C48 C49 Br49 -179.2(4) . . . . ?
C48 C49 C50 C51 0.5(8) . . . . ?
Br49 C49 C50 C51 179.4(4) . . . . ?
C49 C50 C51 C46 -0.6(8) . . . . ?
C47 C46 C51 C50 0.5(8) . . . . ?
C35 C46 C51 C50 -179.4(5) . . . . ?
C37 C36 C52 C53 -121.2(5) . . . . ?
C35 C36 C52 C53 112.8(5) . . . . ?
C37 C36 C52 C57 58.2(6) . . . . ?
C35 C36 C52 C57 -67.8(6) . . . . ?
C57 C52 C53 C54 1.6(8) . . . . ?
C36 C52 C53 C54 -178.9(5) . . . . ?
C52 C53 C54 C55 -0.7(8) . . . . ?
C53 C54 C55 C56 -0.6(8) . . . . ?
C54 C55 C56 C57 1.0(8) . . . . ?
C55 C56 C57 C52 -0.1(8) . . . . ?
C53 C52 C57 C56 -1.2(8) . . . . ?
C36 C52 C57 C56 179.4(5) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


