# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cu_ntnu_a
_database_code_depnum_ccdc_archive 'CCDC 1526049'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H18 Br Cl F3 N O7'
_chemical_formula_sum            'C30 H18 Br Cl F3 N O7'
_chemical_formula_weight         676.81
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 31 2 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   11.2302(2)
_cell_length_b                   11.2302(2)
_cell_length_c                   76.8595(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     8394.7(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9755
_cell_measurement_theta_min      4.03
_cell_measurement_theta_max      66.74

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4080
_exptl_absorpt_coefficient_mu    3.508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2485
_exptl_absorpt_correction_T_max  0.3731
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            75593
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -91
_diffrn_reflns_limit_l_max       90
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         66.89
_reflns_number_total             9949
_reflns_number_gt                9878
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+5.8946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.037(13)
_refine_ls_number_reflns         9949
_refine_ls_number_parameters     779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7751(3) 0.6148(3) 0.77137(5) 0.0475(7) Uani 1 1 d . . .
C2 C 0.6660(4) 0.5834(4) 0.76068(4) 0.0514(8) Uani 1 1 d . . .
H2 H 0.6808 0.6135 0.7492 0.062 Uiso 1 1 calc R . .
C3 C 0.5338(3) 0.5068(4) 0.76703(4) 0.0436(7) Uani 1 1 d . . .
H3 H 0.4598 0.4842 0.7597 0.052 Uiso 1 1 calc R . .
C4 C 0.5092(3) 0.4624(3) 0.78433(4) 0.0367(6) Uani 1 1 d . . .
C5 C 0.6226(3) 0.4949(3) 0.79463(4) 0.0429(7) Uani 1 1 d . . .
H5 H 0.6093 0.4645 0.8061 0.052 Uiso 1 1 calc R . .
C6 C 0.7544(4) 0.5711(4) 0.78833(4) 0.0488(8) Uani 1 1 d . . .
H6 H 0.8291 0.5929 0.7955 0.059 Uiso 1 1 calc R . .
C7 C 0.3631(3) 0.3601(3) 0.79022(3) 0.0348(6) Uani 1 1 d . . .
C8 C 0.3185(3) 0.3591(3) 0.80975(4) 0.0394(6) Uani 1 1 d . . .
C9 C 0.3888(5) 0.4870(4) 0.82149(4) 0.0571(10) Uani 1 1 d . . .
C10 C 0.1322(3) 0.3297(3) 0.79313(4) 0.0448(7) Uani 1 1 d . . .
C11 C 0.2416(3) 0.3531(3) 0.77946(4) 0.0393(6) Uani 1 1 d . . .
C12 C 0.2587(3) 0.4763(4) 0.76916(4) 0.0463(8) Uani 1 1 d . . .
C13 C 0.3037(6) 0.7044(5) 0.77181(7) 0.0775(13) Uani 1 1 d . . .
H13A H 0.2239 0.6777 0.7645 0.093 Uiso 1 1 calc R . .
H13B H 0.3856 0.7536 0.7647 0.093 Uiso 1 1 calc R . .
C14 C 0.3060(7) 0.7925(6) 0.78616(8) 0.0965(17) Uani 1 1 d . . .
H14A H 0.3080 0.8726 0.7815 0.145 Uiso 1 1 calc R . .
H14B H 0.3864 0.8198 0.7932 0.145 Uiso 1 1 calc R . .
H14C H 0.2253 0.7423 0.7932 0.145 Uiso 1 1 calc R . .
C15 C 0.2030(3) 0.1277(3) 0.77780(4) 0.0419(7) Uani 1 1 d . . .
H15 H 0.2141 0.0673 0.7696 0.050 Uiso 1 1 calc R . .
C16 C 0.0797(3) 0.0411(3) 0.78922(4) 0.0427(7) Uani 1 1 d . . .
C17 C -0.0540(4) 0.0015(3) 0.78398(5) 0.0507(8) Uani 1 1 d . . .
H17 H -0.0685 0.0336 0.7735 0.061 Uiso 1 1 calc R . .
C18 C -0.1651(4) -0.0847(4) 0.79423(5) 0.0541(9) Uani 1 1 d . . .
C19 C -0.1471(4) -0.1346(4) 0.80989(5) 0.0583(9) Uani 1 1 d . . .
H19 H -0.2225 -0.1931 0.8167 0.070 Uiso 1 1 calc R . .
C20 C -0.0148(4) -0.0959(4) 0.81528(5) 0.0524(8) Uani 1 1 d . . .
H20 H -0.0006 -0.1286 0.8257 0.063 Uiso 1 1 calc R . .
C21 C 0.0966(3) -0.0079(3) 0.80499(4) 0.0427(7) Uani 1 1 d . . .
C22 C 0.3331(3) 0.1581(3) 0.80711(3) 0.0352(6) Uani 1 1 d . . .
C23 C 0.4670(3) 0.1629(3) 0.80985(4) 0.0390(6) Uani 1 1 d . . .
C24 C 0.5233(4) 0.1538(3) 0.82549(4) 0.0463(7) Uani 1 1 d . . .
H24 H 0.4770 0.1418 0.8360 0.056 Uiso 1 1 calc R . .
C25 C 0.6501(4) 0.1632(4) 0.82497(5) 0.0568(9) Uani 1 1 d . . .
H25 H 0.6899 0.1568 0.8353 0.068 Uiso 1 1 calc R . .
C26 C 0.7203(4) 0.1819(4) 0.80937(6) 0.0614(10) Uani 1 1 d . . .
H26 H 0.8058 0.1874 0.8094 0.074 Uiso 1 1 calc R . .
C27 C 0.6653(4) 0.1924(4) 0.79396(5) 0.0565(9) Uani 1 1 d . . .
H27 H 0.7124 0.2056 0.7835 0.068 Uiso 1 1 calc R . .
C28 C 0.5359(3) 0.1827(3) 0.79435(4) 0.0426(7) Uani 1 1 d . . .
C29 C 0.4573(3) 0.1982(3) 0.78013(4) 0.0419(7) Uani 1 1 d . . .
C30 C 0.3359(3) 0.2075(3) 0.78838(3) 0.0352(6) Uani 1 1 d . . .
C31 C 0.7082(4) 1.2043(5) 0.73551(5) 0.0701(13) Uani 1 1 d . . .
C32 C 0.6623(4) 1.0755(5) 0.74133(5) 0.0677(12) Uani 1 1 d . A .
H32 H 0.6981 1.0611 0.7515 0.081 Uiso 1 1 calc R . .
C33 C 0.5620(4) 0.9648(4) 0.73216(4) 0.0531(8) Uani 1 1 d . . .
H33 H 0.5280 0.8764 0.7365 0.064 Uiso 1 1 calc R A .
C34 C 0.5105(3) 0.9833(3) 0.71641(4) 0.0417(7) Uani 1 1 d . A .
C35 C 0.5556(4) 1.1160(4) 0.71148(4) 0.0535(8) Uani 1 1 d . . .
H35 H 0.5189 1.1320 0.7015 0.064 Uiso 1 1 calc R A .
C36 C 0.6541(5) 1.2274(5) 0.72076(5) 0.0712(12) Uani 1 1 d . A .
H36 H 0.6832 1.3166 0.7170 0.085 Uiso 1 1 calc R . .
C37 C 0.3944(3) 0.8567(3) 0.70759(3) 0.0347(6) Uani 1 1 d . . .
C38 C 0.3690(3) 0.8551(3) 0.68714(3) 0.0352(6) Uani 1 1 d . A .
C39 C 0.4783(4) 0.9527(4) 0.67437(4) 0.0556(9) Uani 1 1 d . . .
C40 C 0.3496(3) 0.6428(3) 0.69325(4) 0.0431(7) Uani 1 1 d . . .
C41 C 0.3920(3) 0.7182(3) 0.71092(4) 0.0397(6) Uani 1 1 d . A .
C42 C 0.5224(4) 0.7162(4) 0.71589(5) 0.0527(8) Uani 1 1 d . . .
C43 C 0.7498(5) 0.7859(8) 0.70640(8) 0.1001(19) Uani 1 1 d . . .
H43A H 0.8012 0.8139 0.6956 0.120 Uiso 1 1 calc R A .
H43B H 0.7304 0.6936 0.7091 0.120 Uiso 1 1 calc R . .
C44 C 0.8357(6) 0.8838(9) 0.72093(11) 0.136(3) Uani 1 1 d . A .
H44A H 0.9206 0.8834 0.7220 0.204 Uiso 1 1 calc R . .
H44B H 0.7857 0.8545 0.7317 0.204 Uiso 1 1 calc R . .
H44C H 0.8547 0.9751 0.7182 0.204 Uiso 1 1 calc R . .
C45 C 0.1752(3) 0.6726(3) 0.72070(4) 0.0374(6) Uani 1 1 d . . .
H45 H 0.1277 0.6645 0.7317 0.045 Uiso 1 1 calc R A .
C46 C 0.0703(3) 0.5785(3) 0.70734(4) 0.0380(6) Uani 1 1 d . A .
C47 C 0.0333(3) 0.4410(3) 0.70594(5) 0.0477(7) Uani 1 1 d . . .
H47 H 0.0752 0.4051 0.7130 0.057 Uiso 1 1 calc R A .
C48 C -0.0651(4) 0.3586(4) 0.69419(5) 0.0568(9) Uani 1 1 d . A .
C49 C -0.1308(4) 0.4069(4) 0.68364(5) 0.0568(9) Uani 1 1 d . . .
H49 H -0.1984 0.3487 0.6759 0.068 Uiso 1 1 calc R A .
C50 C -0.0940(3) 0.5441(4) 0.68487(5) 0.0503(8) Uani 1 1 d . A .
H50 H -0.1371 0.5792 0.6779 0.060 Uiso 1 1 calc R . .
C51 C 0.0070(3) 0.6283(3) 0.69646(4) 0.0419(7) Uani 1 1 d . . .
C52 C 0.1814(3) 0.8595(3) 0.69992(4) 0.0360(6) Uani 1 1 d . . .
C53 C 0.2014(3) 0.9987(3) 0.70422(4) 0.0409(6) Uani 1 1 d . A .
C54 C 0.1852(4) 1.0878(4) 0.69348(5) 0.0557(9) Uani 1 1 d . . .
H54 H 0.1519 1.0620 0.6822 0.067 Uiso 1 1 calc R A .
C55 C 0.2193(5) 1.2161(4) 0.69976(6) 0.0730(12) Uani 1 1 d . A .
H55 H 0.2116 1.2787 0.6926 0.088 Uiso 1 1 calc R . .
C56 C 0.2654(5) 1.2520(5) 0.71683(7) 0.0755(12) Uani 1 1 d . . .
H56 H 0.2865 1.3383 0.7209 0.091 Uiso 1 1 calc R A .
C57 C 0.2809(4) 1.1639(4) 0.72784(5) 0.0636(10) Uani 1 1 d . A .
H57 H 0.3121 1.1892 0.7392 0.076 Uiso 1 1 calc R . .
C58 C 0.2477(4) 1.0348(4) 0.72126(4) 0.0462(7) Uani 1 1 d . . .
C59 C 0.2579(3) 0.9226(3) 0.72947(4) 0.0407(7) Uani 1 1 d . A .
C60 C 0.2491(3) 0.8242(3) 0.71484(3) 0.0347(6) Uani 1 1 d . A .
N1 N 0.1971(3) 0.2362(3) 0.76805(3) 0.0481(7) Uani 1 1 d . . .
N2 N 0.2868(3) 0.6457(4) 0.72387(4) 0.0568(8) Uani 1 1 d . A .
O1 O 0.3231(2) 0.2546(2) 0.81860(2) 0.0418(5) Uani 1 1 d . . .
O2 O 0.1791(2) 0.3289(3) 0.80935(3) 0.0487(5) Uani 1 1 d . . .
O3 O 0.0205(3) 0.3115(3) 0.79043(4) 0.0627(7) Uani 1 1 d . . .
O4 O 0.2312(3) 0.4707(3) 0.75396(3) 0.0624(7) Uani 1 1 d . . .
O5 O 0.2981(3) 0.5828(3) 0.77950(3) 0.0576(6) Uani 1 1 d . . .
O6 O 0.2258(2) 0.0252(2) 0.81094(3) 0.0443(5) Uani 1 1 d . . .
O7 O 0.4773(3) 0.2005(3) 0.76468(3) 0.0570(6) Uani 1 1 d . . .
O8 O 0.2545(2) 0.8674(2) 0.68420(2) 0.0427(5) Uani 1 1 d . A .
O9 O 0.3392(2) 0.7225(2) 0.68103(3) 0.0455(5) Uani 1 1 d . A .
O10 O 0.3270(3) 0.5296(3) 0.69017(4) 0.0615(7) Uani 1 1 d . A .
O11 O 0.5287(3) 0.6521(3) 0.72781(4) 0.0699(8) Uani 1 1 d . A .
O12 O 0.6213(3) 0.7864(4) 0.70432(4) 0.0723(8) Uani 1 1 d . A .
O13 O 0.2637(3) 0.9029(3) 0.74477(3) 0.0540(6) Uani 1 1 d . . .
O14 O 0.0411(2) 0.7659(2) 0.69715(3) 0.0445(5) Uani 1 1 d . A .
Cl1 Cl -0.32958(10) -0.13389(12) 0.787280(18) 0.0807(3) Uani 1 1 d . . .
Cl2 Cl -0.10783(13) 0.18799(11) 0.69225(2) 0.0938(4) Uani 1 1 d . . .
Br1 Br 0.95705(4) 0.71934(5) 0.762503(6) 0.06719(13) Uani 1 1 d . . .
Br2 Br 0.8390(5) 1.3699(4) 0.74707(6) 0.0963(12) Uani 0.50(2) 1 d P A 1
Br2' Br 0.8564(7) 1.3377(13) 0.74861(6) 0.130(2) Uani 0.50(2) 1 d P A 2
F1 F 0.5079(3) 0.5109(3) 0.82772(3) 0.0920(9) Uani 1 1 d . . .
F2 F 0.3117(4) 0.4696(3) 0.83531(3) 0.0918(7) Uani 1 1 d . . .
F3 F 0.4080(4) 0.5966(3) 0.81307(3) 0.0918(7) Uani 1 1 d . . .
F4 F 0.4961(4) 1.0773(2) 0.67447(3) 0.0929(10) Uani 1 1 d . A .
F5 F 0.4407(3) 0.9058(3) 0.65814(2) 0.0725(7) Uani 1 1 d . A .
F6 F 0.5978(2) 0.9611(4) 0.67728(3) 0.0965(10) Uani 1 1 d . A .
H1' H 0.1389 0.2226 0.7587 0.116 Uiso 1 1 d R . .
H2' H 0.3004 0.6002 0.7308 0.116 Uiso 1 1 d 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
C1 C2 1.366(5) . ?
C1 C6 1.371(5) . ?
C1 Br1 1.903(3) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 C7 1.527(4) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.563(4) . ?
C7 C8 1.581(4) . ?
C7 C30 1.589(4) . ?
C8 O1 1.379(4) . ?
C8 O2 1.427(4) . ?
C8 C9 1.538(5) . ?
C9 F3 1.310(5) . ?
C9 F1 1.315(5) . ?
C9 F2 1.322(4) . ?
C10 O3 1.184(4) . ?
C10 O2 1.356(4) . ?
C10 C11 1.536(4) . ?
C11 N1 1.444(4) . ?
C11 C12 1.521(4) . ?
C12 O4 1.202(4) . ?
C12 O5 1.316(5) . ?
C13 O5 1.460(4) . ?
C13 C14 1.473(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N1 1.459(4) . ?
C15 C16 1.512(4) . ?
C15 C30 1.535(4) . ?
C15 H15 0.9800 . ?
C16 C21 1.383(5) . ?
C16 C17 1.396(5) . ?
C17 C18 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(6) . ?
C18 Cl1 1.727(4) . ?
C19 C20 1.386(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(5) . ?
C20 H20 0.9300 . ?
C21 O6 1.384(4) . ?
C22 O6 1.403(4) . ?
C22 O1 1.446(3) . ?
C22 C23 1.492(4) . ?
C22 C30 1.538(4) . ?
C23 C28 1.377(4) . ?
C23 C24 1.385(4) . ?
C24 C25 1.375(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.402(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.469(5) . ?
C29 O7 1.206(4) . ?
C29 C30 1.554(4) . ?
C31 C32 1.346(7) . ?
C31 C36 1.370(7) . ?
C31 Br2' 1.881(5) . ?
C31 Br2 1.917(5) . ?
C32 C33 1.383(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.401(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.365(5) . ?
C34 C37 1.526(4) . ?
C35 C36 1.383(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C41 1.563(4) . ?
C37 C60 1.585(4) . ?
C37 C38 1.596(3) . ?
C38 O8 1.380(4) . ?
C38 O9 1.432(4) . ?
C38 C39 1.525(4) . ?
C39 F4 1.310(5) . ?
C39 F6 1.317(5) . ?
C39 F5 1.337(4) . ?
C40 O10 1.188(4) . ?
C40 O9 1.343(4) . ?
C40 C41 1.544(5) . ?
C41 N2 1.445(4) . ?
C41 C42 1.525(5) . ?
C42 O11 1.189(4) . ?
C42 O12 1.330(5) . ?
C43 O12 1.456(5) . ?
C43 C44 1.525(10) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 N2 1.449(4) . ?
C45 C46 1.521(4) . ?
C45 C60 1.541(4) . ?
C45 H45 0.9800 . ?
C46 C51 1.384(4) . ?
C46 C47 1.388(5) . ?
C47 C48 1.368(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.377(6) . ?
C48 Cl2 1.733(4) . ?
C49 C50 1.384(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.379(5) . ?
C50 H50 0.9300 . ?
C51 O14 1.395(4) . ?
C52 O14 1.406(4) . ?
C52 O8 1.438(3) . ?
C52 C53 1.501(4) . ?
C52 C60 1.533(4) . ?
C53 C54 1.378(5) . ?
C53 C58 1.392(4) . ?
C54 C55 1.380(6) . ?
C54 H54 0.9300 . ?
C55 C56 1.394(7) . ?
C55 H55 0.9300 . ?
C56 C57 1.377(6) . ?
C56 H56 0.9300 . ?
C57 C58 1.399(5) . ?
C57 H57 0.9300 . ?
C58 C59 1.464(5) . ?
C59 O13 1.205(4) . ?
C59 C60 1.544(4) . ?
N1 H1' 0.9310 . ?
N2 H2' 0.8049 . ?

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 C1 C6 120.7(3) . . ?
C2 C1 Br1 119.4(3) . . ?
C6 C1 Br1 119.9(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.2(3) . . ?
C5 C4 C7 122.0(3) . . ?
C3 C4 C7 119.8(3) . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 C7 C11 117.6(2) . . ?
C4 C7 C8 120.3(2) . . ?
C11 C7 C8 103.7(2) . . ?
C4 C7 C30 109.8(2) . . ?
C11 C7 C30 101.9(2) . . ?
C8 C7 C30 100.8(2) . . ?
O1 C8 O2 108.1(3) . . ?
O1 C8 C9 106.6(3) . . ?
O2 C8 C9 103.0(3) . . ?
O1 C8 C7 109.1(2) . . ?
O2 C8 C7 106.7(2) . . ?
C9 C8 C7 122.5(3) . . ?
F3 C9 F1 108.4(4) . . ?
F3 C9 F2 108.9(3) . . ?
F1 C9 F2 105.2(3) . . ?
F3 C9 C8 110.7(3) . . ?
F1 C9 C8 113.5(3) . . ?
F2 C9 C8 110.0(3) . . ?
O3 C10 O2 122.8(3) . . ?
O3 C10 C11 126.7(3) . . ?
O2 C10 C11 110.5(3) . . ?
N1 C11 C12 109.9(3) . . ?
N1 C11 C10 112.1(3) . . ?
C12 C11 C10 103.8(2) . . ?
N1 C11 C7 105.3(2) . . ?
C12 C11 C7 121.3(3) . . ?
C10 C11 C7 104.5(2) . . ?
O4 C12 O5 126.5(3) . . ?
O4 C12 C11 123.1(3) . . ?
O5 C12 C11 110.2(3) . . ?
O5 C13 C14 107.6(4) . . ?
O5 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O5 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 115.2(3) . . ?
N1 C15 C30 102.8(2) . . ?
C16 C15 C30 112.3(2) . . ?
N1 C15 H15 108.8 . . ?
C16 C15 H15 108.8 . . ?
C30 C15 H15 108.8 . . ?
C21 C16 C17 117.8(3) . . ?
C21 C16 C15 120.1(3) . . ?
C17 C16 C15 122.1(3) . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 Cl1 119.6(3) . . ?
C19 C18 Cl1 119.3(3) . . ?
C18 C19 C20 118.9(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 O6 121.2(3) . . ?
C16 C21 C20 121.9(3) . . ?
O6 C21 C20 116.9(3) . . ?
O6 C22 O1 108.8(2) . . ?
O6 C22 C23 108.8(2) . . ?
O1 C22 C23 110.0(2) . . ?
O6 C22 C30 115.6(2) . . ?
O1 C22 C30 107.3(2) . . ?
C23 C22 C30 106.3(2) . . ?
C28 C23 C24 121.5(3) . . ?
C28 C23 C22 111.0(3) . . ?
C24 C23 C22 127.5(3) . . ?
C25 C24 C23 117.5(3) . . ?
C25 C24 H24 121.2 . . ?
C23 C24 H24 121.2 . . ?
C24 C25 C26 121.6(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C27 C26 C25 120.8(4) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 118.0(4) . . ?
C26 C27 H27 121.0 . . ?
C28 C27 H27 121.0 . . ?
C23 C28 C27 120.5(3) . . ?
C23 C28 C29 109.9(3) . . ?
C27 C28 C29 129.5(3) . . ?
O7 C29 C28 128.2(3) . . ?
O7 C29 C30 124.1(3) . . ?
C28 C29 C30 107.7(2) . . ?
C15 C30 C22 116.5(3) . . ?
C15 C30 C29 112.0(2) . . ?
C22 C30 C29 102.6(2) . . ?
C15 C30 C7 106.5(2) . . ?
C22 C30 C7 105.3(2) . . ?
C29 C30 C7 114.0(2) . . ?
C32 C31 C36 120.7(4) . . ?
C32 C31 Br2' 112.8(6) . . ?
C36 C31 Br2' 126.3(6) . . ?
C32 C31 Br2 125.7(4) . . ?
C36 C31 Br2 113.4(4) . . ?
Br2' C31 Br2 15.2(5) . . ?
C31 C32 C33 119.9(4) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 C34 121.2(4) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 116.5(3) . . ?
C35 C34 C37 124.9(3) . . ?
C33 C34 C37 118.0(3) . . ?
C34 C35 C36 122.4(4) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C31 C36 C35 119.0(4) . . ?
C31 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C34 C37 C41 115.9(3) . . ?
C34 C37 C60 111.1(2) . . ?
C41 C37 C60 102.1(2) . . ?
C34 C37 C38 120.8(2) . . ?
C41 C37 C38 103.7(2) . . ?
C60 C37 C38 100.7(2) . . ?
O8 C38 O9 107.8(2) . . ?
O8 C38 C39 106.1(3) . . ?
O9 C38 C39 102.8(2) . . ?
O8 C38 C37 109.3(2) . . ?
O9 C38 C37 106.4(2) . . ?
C39 C38 C37 123.4(3) . . ?
F4 C39 F6 108.4(4) . . ?
F4 C39 F5 106.0(3) . . ?
F6 C39 F5 107.2(3) . . ?
F4 C39 C38 113.7(3) . . ?
F6 C39 C38 111.5(3) . . ?
F5 C39 C38 109.6(3) . . ?
O10 C40 O9 122.0(3) . . ?
O10 C40 C41 127.2(3) . . ?
O9 C40 C41 110.8(3) . . ?
N2 C41 C42 109.9(3) . . ?
N2 C41 C40 110.8(3) . . ?
C42 C41 C40 104.3(3) . . ?
N2 C41 C37 106.0(3) . . ?
C42 C41 C37 121.1(3) . . ?
C40 C41 C37 104.4(2) . . ?
O11 C42 O12 126.2(4) . . ?
O11 C42 C41 123.4(3) . . ?
O12 C42 C41 110.3(3) . . ?
O12 C43 C44 110.4(5) . . ?
O12 C43 H43A 109.6 . . ?
C44 C43 H43A 109.6 . . ?
O12 C43 H43B 109.6 . . ?
C44 C43 H43B 109.6 . . ?
H43A C43 H43B 108.1 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N2 C45 C46 114.7(3) . . ?
N2 C45 C60 103.6(3) . . ?
C46 C45 C60 111.9(2) . . ?
N2 C45 H45 108.8 . . ?
C46 C45 H45 108.8 . . ?
C60 C45 H45 108.8 . . ?
C51 C46 C47 118.3(3) . . ?
C51 C46 C45 120.2(3) . . ?
C47 C46 C45 121.5(3) . . ?
C48 C47 C46 119.7(3) . . ?
C48 C47 H47 120.2 . . ?
C46 C47 H47 120.2 . . ?
C47 C48 C49 122.2(3) . . ?
C47 C48 Cl2 119.2(3) . . ?
C49 C48 Cl2 118.6(3) . . ?
C48 C49 C50 118.5(3) . . ?
C48 C49 H49 120.7 . . ?
C50 C49 H49 120.7 . . ?
C51 C50 C49 119.5(3) . . ?
C51 C50 H50 120.2 . . ?
C49 C50 H50 120.2 . . ?
C50 C51 C46 121.7(3) . . ?
C50 C51 O14 117.4(3) . . ?
C46 C51 O14 120.9(3) . . ?
O14 C52 O8 108.1(2) . . ?
O14 C52 C53 109.8(3) . . ?
O8 C52 C53 109.7(2) . . ?
O14 C52 C60 115.8(2) . . ?
O8 C52 C60 107.7(2) . . ?
C53 C52 C60 105.6(2) . . ?
C54 C53 C58 121.2(3) . . ?
C54 C53 C52 128.3(3) . . ?
C58 C53 C52 110.5(3) . . ?
C53 C54 C55 118.8(4) . . ?
C53 C54 H54 120.6 . . ?
C55 C54 H54 120.6 . . ?
C54 C55 C56 120.0(4) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C57 C56 C55 122.2(4) . . ?
C57 C56 H56 118.9 . . ?
C55 C56 H56 118.9 . . ?
C56 C57 C58 117.3(4) . . ?
C56 C57 H57 121.4 . . ?
C58 C57 H57 121.4 . . ?
C53 C58 C57 120.6(3) . . ?
C53 C58 C59 109.5(3) . . ?
C57 C58 C59 129.9(3) . . ?
O13 C59 C58 127.9(3) . . ?
O13 C59 C60 124.7(3) . . ?
C58 C59 C60 107.3(2) . . ?
C52 C60 C45 116.2(2) . . ?
C52 C60 C59 102.8(2) . . ?
C45 C60 C59 112.6(2) . . ?
C52 C60 C37 105.3(2) . . ?
C45 C60 C37 106.3(2) . . ?
C59 C60 C37 113.7(2) . . ?
C11 N1 C15 107.9(2) . . ?
C11 N1 H1' 120.9 . . ?
C15 N1 H1' 125.5 . . ?
C41 N2 C45 108.4(2) . . ?
C41 N2 H2' 116.9 . . ?
C45 N2 H2' 134.7 . . ?
C8 O1 C22 112.7(2) . . ?
C10 O2 C8 113.7(2) . . ?
C12 O5 C13 116.3(3) . . ?
C21 O6 C22 116.3(2) . . ?
C38 O8 C52 112.8(2) . . ?
C40 O9 C38 114.3(2) . . ?
C42 O12 C43 117.3(4) . . ?
C51 O14 C52 114.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.89
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_ch17409
_database_code_depnum_ccdc_archive 'CCDC 1473859'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H24 Br2 F3 N O8'
_chemical_formula_sum            'C32 H24 Br2 F3 N O8'
_chemical_formula_weight         767.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7847(11)
_cell_length_b                   13.1195(16)
_cell_length_c                   13.9270(15)
_cell_angle_alpha                113.199(8)
_cell_angle_beta                 98.631(9)
_cell_angle_gamma                105.657(9)
_cell_volume                     1514.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1157
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      17.46

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4377
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13614
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_av_sigmaI/netI    0.2320
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.15
_reflns_number_total             5345
_reflns_number_gt                2177
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1098P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5345
_refine_ls_number_parameters     415
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.2017
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.2121
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_restrained_S_all      0.842
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2790(11) 0.3894(9) 1.1889(7) 0.040(3) Uani 1 1 d . . .
C2 C 0.2373(10) 0.2702(8) 1.1220(7) 0.035(2) Uani 1 1 d . . .
H2 H 0.1986 0.2145 1.1468 0.042 Uiso 1 1 calc R . .
C3 C 0.2524(10) 0.2320(7) 1.0174(6) 0.026(2) Uani 1 1 d . . .
C4 C 0.3008(10) 0.3151(8) 0.9810(6) 0.031(2) Uani 1 1 d . . .
C5 C 0.3438(11) 0.4358(8) 1.0487(7) 0.040(3) Uani 1 1 d . . .
H5 H 0.3782 0.4919 1.0235 0.048 Uiso 1 1 calc R . .
C6 C 0.3346(11) 0.4714(8) 1.1542(7) 0.038(3) Uani 1 1 d . . .
H6 H 0.3670 0.5530 1.2025 0.046 Uiso 1 1 calc R . .
C7 C 0.2108(10) 0.1035(7) 0.9393(6) 0.029(2) Uani 1 1 d . . .
H7 H 0.1454 0.0530 0.9638 0.034 Uiso 1 1 calc R . .
C9 C 0.2910(10) -0.0452(8) 0.8300(7) 0.030(2) Uani 1 1 d . . .
C10 C 0.1953(13) -0.1423(8) 0.8549(7) 0.032(2) Uani 1 1 d . . .
C11 C 0.1880(14) -0.2920(12) 0.9107(13) 0.094(5) Uani 1 1 d DU . .
H11A H 0.1504 -0.2512 0.9704 0.113 Uiso 1 1 calc R . .
H11B H 0.1039 -0.3566 0.8500 0.113 Uiso 1 1 calc R . .
C12 C 0.2920(15) -0.3388(11) 0.9471(10) 0.092(5) Uani 1 1 d DU . .
H12A H 0.2426 -0.3948 0.9713 0.138 Uiso 1 1 calc R . .
H12B H 0.3746 -0.2740 1.0071 0.138 Uiso 1 1 calc R . .
H12C H 0.3283 -0.3788 0.8873 0.138 Uiso 1 1 calc R . .
C13 C 0.4334(12) -0.0739(8) 0.8118(7) 0.031(2) Uani 1 1 d . . .
C14 C 0.5268(11) -0.2043(9) 0.6930(8) 0.051(3) Uani 1 1 d . . .
H14A H 0.5403 -0.2499 0.7326 0.061 Uiso 1 1 calc R . .
H14B H 0.6196 -0.1369 0.7172 0.061 Uiso 1 1 calc R . .
C15 C 0.1937(10) -0.0239(7) 0.7435(6) 0.026(2) Uani 1 1 d . . .
C16 C 0.2964(10) 0.0547(8) 0.7014(7) 0.028(2) Uani 1 1 d . . .
C17 C 0.3073(14) 0.0003(10) 0.5834(8) 0.045(3) Uani 1 1 d . . .
C18 C 0.1850(11) 0.1802(8) 0.7943(7) 0.033(2) Uani 1 1 d . . .
C19 C 0.1350(9) 0.0713(7) 0.8195(6) 0.022(2) Uani 1 1 d . . .
C20 C -0.0339(11) 0.0442(8) 0.8048(7) 0.030(2) Uani 1 1 d . . .
C21 C -0.0714(11) 0.1340(7) 0.7790(7) 0.030(2) Uani 1 1 d . . .
C22 C -0.2086(12) 0.1474(9) 0.7619(8) 0.044(3) Uani 1 1 d . . .
H22 H -0.2924 0.0941 0.7646 0.052 Uiso 1 1 calc R . .
C23 C -0.2194(12) 0.2383(9) 0.7412(8) 0.045(3) Uani 1 1 d . . .
H23 H -0.3109 0.2485 0.7299 0.053 Uiso 1 1 calc R . .
C24 C -0.0933(13) 0.3170(9) 0.7369(8) 0.049(3) Uani 1 1 d . . .
H24 H -0.1026 0.3784 0.7208 0.059 Uiso 1 1 calc R . .
C25 C 0.0432(11) 0.3068(8) 0.7555(7) 0.037(3) Uani 1 1 d . . .
H25 H 0.1273 0.3614 0.7546 0.045 Uiso 1 1 calc R . .
C26 C 0.0521(11) 0.2128(8) 0.7757(7) 0.030(2) Uani 1 1 d . . .
C27 C 0.0700(11) -0.1335(8) 0.6479(7) 0.032(2) Uani 1 1 d . . .
C28 C 0.0770(11) -0.2468(8) 0.6146(7) 0.038(3) Uani 1 1 d . . .
H28 H 0.1569 -0.2573 0.6513 0.045 Uiso 1 1 calc R . .
C29 C -0.0350(13) -0.3443(9) 0.5267(8) 0.047(3) Uani 1 1 d . . .
H29 H -0.0311 -0.4208 0.5038 0.057 Uiso 1 1 calc R . .
C30 C -0.1512(12) -0.3282(8) 0.4735(7) 0.038(3) Uani 1 1 d . . .
C31 C -0.1556(12) -0.2179(9) 0.5036(7) 0.041(3) Uani 1 1 d . . .
H31 H -0.2353 -0.2083 0.4658 0.049 Uiso 1 1 calc R . .
C32 C -0.0450(11) -0.1195(8) 0.5890(7) 0.034(2) Uani 1 1 d . . .
H32 H -0.0474 -0.0431 0.6072 0.041 Uiso 1 1 calc R . .
C33 C 0.4876(13) -0.2809(10) 0.5737(8) 0.063(4) Uani 1 1 d . . .
H33A H 0.5663 -0.3105 0.5572 0.095 Uiso 1 1 calc R . .
H33B H 0.4751 -0.2349 0.5353 0.095 Uiso 1 1 calc R . .
H33C H 0.3959 -0.3474 0.5507 0.095 Uiso 1 1 calc R . .
N1 N 0.3402(8) 0.0700(6) 0.9275(5) 0.0268(18) Uani 1 1 d . . .
H1 H 0.4303 0.1110 0.9705 0.032 Uiso 1 1 calc R . .
O1 O 0.0728(8) -0.1537(6) 0.8618(5) 0.049(2) Uani 1 1 d . . .
O2 O 0.2702(8) -0.2066(6) 0.8745(6) 0.054(2) Uani 1 1 d . . .
O3 O 0.5479(8) -0.0228(6) 0.8825(5) 0.0399(18) Uani 1 1 d . . .
O4 O 0.4063(7) -0.1615(5) 0.7151(5) 0.0375(17) Uani 1 1 d . . .
O5 O 0.4432(7) 0.1086(5) 0.7652(5) 0.0344(16) Uani 1 1 d . . .
H5A H 0.4466 0.1400 0.8306 0.052 Uiso 1 1 calc R . .
O6 O 0.2304(6) 0.1391(5) 0.7003(4) 0.0299(16) Uani 1 1 d . . .
O7 O -0.1149(7) -0.0301(5) 0.8207(5) 0.0383(17) Uani 1 1 d . . .
O8 O 0.3117(6) 0.2800(5) 0.8761(4) 0.0300(15) Uani 1 1 d . . .
Br1 Br 0.25455(14) 0.43762(10) 1.33033(8) 0.0598(4) Uani 1 1 d . . .
Br2 Br -0.30923(14) -0.46208(10) 0.35809(8) 0.0622(4) Uani 1 1 d . . .
F1 F 0.3511(7) -0.0925(5) 0.5616(4) 0.0609(18) Uani 1 1 d . . .
F2 F 0.4071(7) 0.0810(5) 0.5698(4) 0.0538(17) Uani 1 1 d . . .
F3 F 0.1810(7) -0.0361(5) 0.5080(4) 0.0460(15) Uani 1 1 d . . .


_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
C1 C6 1.365(12) . ?
C1 C2 1.369(12) . ?
C1 Br1 1.892(8) . ?
C2 C3 1.388(10) . ?
C2 H2 0.9400 . ?
C3 C4 1.377(11) . ?
C3 C7 1.498(11) . ?
C4 O8 1.378(9) . ?
C4 C5 1.386(11) . ?
C5 C6 1.380(12) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 N1 1.459(10) . ?
C7 C19 1.555(11) . ?
C7 H7 0.9900 . ?
C9 N1 1.468(10) . ?
C9 C10 1.556(13) . ?
C9 C13 1.569(12) . ?
C9 C15 1.581(11) . ?
C10 O1 1.191(10) . ?
C10 O2 1.334(11) . ?
C11 C12 1.448(12) . ?
C11 O2 1.495(12) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 O3 1.190(10) . ?
C13 O4 1.309(10) . ?
C14 O4 1.459(10) . ?
C14 C33 1.484(12) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C27 1.541(12) . ?
C15 C16 1.584(12) . ?
C15 C19 1.594(10) . ?
C16 O5 1.387(10) . ?
C16 O6 1.429(10) . ?
C16 C17 1.546(11) . ?
C17 F2 1.329(12) . ?
C17 F3 1.325(11) . ?
C17 F1 1.337(10) . ?
C18 O6 1.397(9) . ?
C18 O8 1.440(10) . ?
C18 C26 1.492(12) . ?
C18 C19 1.572(12) . ?
C19 C20 1.557(12) . ?
C20 O7 1.198(10) . ?
C20 C21 1.476(12) . ?
C21 C26 1.381(12) . ?
C21 C22 1.398(12) . ?
C22 C23 1.358(13) . ?
C22 H22 0.9400 . ?
C23 C24 1.406(13) . ?
C23 H23 0.9400 . ?
C24 C25 1.374(13) . ?
C24 H24 0.9400 . ?
C25 C26 1.391(12) . ?
C25 H25 0.9400 . ?
C27 C32 1.388(12) . ?
C27 C28 1.397(12) . ?
C28 C29 1.394(13) . ?
C28 H28 0.9400 . ?
C29 C30 1.373(13) . ?
C29 H29 0.9400 . ?
C30 C31 1.353(12) . ?
C30 Br2 1.904(10) . ?
C31 C32 1.379(12) . ?
C31 H31 0.9400 . ?
C32 H32 0.9400 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
N1 H1 0.8700 . ?
O5 H5A 0.8300 . ?

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
C6 C1 C2 121.0(8) . . ?
C6 C1 Br1 120.7(7) . . ?
C2 C1 Br1 118.2(8) . . ?
C1 C2 C3 119.6(9) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 118.9(8) . . ?
C4 C3 C7 118.0(7) . . ?
C2 C3 C7 123.0(8) . . ?
O8 C4 C3 120.5(7) . . ?
O8 C4 C5 118.0(8) . . ?
C3 C4 C5 121.5(7) . . ?
C6 C5 C4 118.2(9) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C1 C6 C5 120.6(8) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C3 112.4(7) . . ?
N1 C7 C19 101.2(6) . . ?
C3 C7 C19 113.6(7) . . ?
N1 C7 H7 109.8 . . ?
C3 C7 H7 109.8 . . ?
C19 C7 H7 109.8 . . ?
N1 C9 C10 108.3(6) . . ?
N1 C9 C13 107.0(7) . . ?
C10 C9 C13 107.0(7) . . ?
N1 C9 C15 101.7(6) . . ?
C10 C9 C15 111.5(7) . . ?
C13 C9 C15 120.6(7) . . ?
O1 C10 O2 123.7(9) . . ?
O1 C10 C9 124.2(9) . . ?
O2 C10 C9 111.9(9) . . ?
C12 C11 O2 106.9(10) . . ?
C12 C11 H11A 110.3 . . ?
O2 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
O2 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 126.6(9) . . ?
O3 C13 C9 121.3(8) . . ?
O4 C13 C9 111.9(8) . . ?
O4 C14 C33 108.1(8) . . ?
O4 C14 H14A 110.1 . . ?
C33 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
C33 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C27 C15 C16 111.4(6) . . ?
C27 C15 C9 117.7(7) . . ?
C16 C15 C9 110.5(7) . . ?
C27 C15 C19 113.8(7) . . ?
C16 C15 C19 100.1(6) . . ?
C9 C15 C19 101.6(6) . . ?
O5 C16 O6 112.4(7) . . ?
O5 C16 C17 103.7(7) . . ?
O6 C16 C17 101.4(7) . . ?
O5 C16 C15 112.9(7) . . ?
O6 C16 C15 105.1(6) . . ?
C17 C16 C15 120.9(8) . . ?
F2 C17 F3 107.0(8) . . ?
F2 C17 F1 107.1(8) . . ?
F3 C17 F1 107.4(9) . . ?
F2 C17 C16 109.8(9) . . ?
F3 C17 C16 113.5(8) . . ?
F1 C17 C16 111.8(8) . . ?
O6 C18 O8 105.5(7) . . ?
O6 C18 C26 112.0(7) . . ?
O8 C18 C26 112.4(7) . . ?
O6 C18 C19 105.6(6) . . ?
O8 C18 C19 114.7(7) . . ?
C26 C18 C19 106.5(7) . . ?
C7 C19 C20 108.2(6) . . ?
C7 C19 C18 112.2(7) . . ?
C20 C19 C18 103.3(7) . . ?
C7 C19 C15 106.7(6) . . ?
C20 C19 C15 121.2(7) . . ?
C18 C19 C15 105.2(6) . . ?
O7 C20 C21 126.6(9) . . ?
O7 C20 C19 125.5(8) . . ?
C21 C20 C19 107.6(8) . . ?
C26 C21 C22 120.5(9) . . ?
C26 C21 C20 111.2(9) . . ?
C22 C21 C20 128.3(9) . . ?
C23 C22 C21 119.2(10) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 119.7(10) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 122.0(10) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C24 C25 C26 117.5(10) . . ?
C24 C25 H25 121.2 . . ?
C26 C25 H25 121.2 . . ?
C21 C26 C25 121.0(9) . . ?
C21 C26 C18 111.2(8) . . ?
C25 C26 C18 127.8(9) . . ?
C32 C27 C28 119.1(9) . . ?
C32 C27 C15 120.1(8) . . ?
C28 C27 C15 120.7(9) . . ?
C27 C28 C29 119.6(10) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C30 C29 C28 119.8(9) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 120.6(10) . . ?
C31 C30 Br2 119.6(9) . . ?
C29 C30 Br2 119.8(8) . . ?
C30 C31 C32 121.0(10) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C31 C32 C27 119.9(9) . . ?
C31 C32 H32 120.1 . . ?
C27 C32 H32 120.1 . . ?
C14 C33 H33A 109.5 . . ?
C14 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C14 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C7 N1 C9 107.7(7) . . ?
C7 N1 H1 126.2 . . ?
C9 N1 H1 126.2 . . ?
C10 O2 C11 113.6(8) . . ?
C13 O4 C14 116.8(7) . . ?
C16 O5 H5A 109.5 . . ?
C18 O6 C16 108.9(6) . . ?
C4 O8 C18 113.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.119
