# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_as55m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(1R,3aS,6R,6aR)-1-(2-bromophenyl)-6-phenyl-hexahydrofuro[3,4-c]furan
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Br O2'
_chemical_formula_sum            'C18 H17 Br O2'
_chemical_formula_weight         345.23

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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P bca'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   9.6034(5)
_cell_length_b                   15.7805(8)
_cell_length_c                   19.7861(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2998.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9815
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    2.743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   'SABABS; Bruker,2001'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26760
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2643
_reflns_number_gt                2176
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0382P)²+2.0300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.14914(4) 0.109098(18) 0.747983(15) 0.06525(14) Uani 1 1 d . . .
C1 C -0.0553(2) 0.24933(15) 0.69100(13) 0.0420(5) Uani 1 1 d . . .
H1 H -0.0622 0.2374 0.7395 0.050 Uiso 1 1 calc R . .
C2 C -0.1469(3) 0.38228(17) 0.69710(18) 0.0573(7) Uani 1 1 d . . .
H2A H -0.1779 0.3864 0.7436 0.069 Uiso 1 1 calc R . .
H2B H -0.1963 0.4243 0.6705 0.069 Uiso 1 1 calc R . .
C3 C 0.0095(3) 0.39691(15) 0.69264(14) 0.0491(6) Uani 1 1 d . . .
H3 H 0.0460 0.4204 0.7349 0.059 Uiso 1 1 calc R . .
C4 C 0.0565(3) 0.44912(18) 0.63211(17) 0.0667(8) Uani 1 1 d . . .
H4A H -0.0217 0.4606 0.6025 0.080 Uiso 1 1 calc R . .
H4B H 0.0953 0.5027 0.6470 0.080 Uiso 1 1 calc R . .
C5 C 0.1198(3) 0.31379(15) 0.60568(13) 0.0437(6) Uani 1 1 d . . .
H5 H 0.0419 0.3011 0.5753 0.052 Uiso 1 1 calc R . .
C6 C 0.0698(2) 0.30790(14) 0.67898(12) 0.0396(5) Uani 1 1 d . . .
H6 H 0.1467 0.2948 0.7098 0.047 Uiso 1 1 calc R . .
C7 C 0.2417(2) 0.25897(15) 0.58737(12) 0.0426(5) Uani 1 1 d . . .
C8 C 0.3740(3) 0.2777(2) 0.61160(15) 0.0564(7) Uani 1 1 d . . .
H8 H 0.3868 0.3255 0.6383 0.068 Uiso 1 1 calc R . .
C9 C 0.4857(3) 0.2272(2) 0.59693(16) 0.0657(8) Uani 1 1 d . . .
H9 H 0.5734 0.2405 0.6137 0.079 Uiso 1 1 calc R . .
C10 C 0.4674(3) 0.1570(2) 0.55757(17) 0.0687(9) Uani 1 1 d . . .
H10 H 0.5429 0.1223 0.5476 0.082 Uiso 1 1 calc R . .
C11 C 0.3384(3) 0.1376(2) 0.53285(18) 0.0693(9) Uani 1 1 d . . .
H11 H 0.3265 0.0897 0.5062 0.083 Uiso 1 1 calc R . .
C12 C 0.2254(3) 0.18885(17) 0.54723(14) 0.0543(7) Uani 1 1 d . . .
H12 H 0.1382 0.1757 0.5297 0.065 Uiso 1 1 calc R . .
C13 C -0.0560(2) 0.16670(14) 0.65319(12) 0.0397(5) Uani 1 1 d . . .
C14 C -0.1391(2) 0.15492(17) 0.59666(14) 0.0486(6) Uani 1 1 d . . .
H14 H -0.1953 0.1991 0.5818 0.058 Uiso 1 1 calc R . .
C15 C -0.1403(3) 0.0787(2) 0.56173(15) 0.0575(7) Uani 1 1 d . . .
H15 H -0.1974 0.0721 0.5241 0.069 Uiso 1 1 calc R . .
C16 C -0.0569(3) 0.01303(18) 0.58271(14) 0.0592(7) Uani 1 1 d . . .
H16 H -0.0583 -0.0383 0.5597 0.071 Uiso 1 1 calc R . .
C17 C 0.0285(3) 0.02354(16) 0.63789(13) 0.0539(7) Uani 1 1 d . . .
H17 H 0.0868 -0.0202 0.6517 0.065 Uiso 1 1 calc R . .
C18 C 0.0274(3) 0.09917(15) 0.67254(12) 0.0439(6) Uani 1 1 d . . .
O1 O -0.17248(17) 0.29926(11) 0.67127(10) 0.0549(5) Uani 1 1 d . . .
O2 O 0.1592(2) 0.40080(11) 0.59754(11) 0.0602(5) 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
Br1 C18 1.903(3) . ?
C1 O1 1.428(3) . ?
C1 C13 1.503(3) . ?
C1 C6 1.534(3) . ?
C1 H1 0.9800 . ?
C2 O1 1.428(3) . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(4) . ?
C3 C6 1.543(3) . ?
C3 H3 0.9800 . ?
C4 O2 1.422(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O2 1.433(3) . ?
C5 C7 1.500(3) . ?
C5 C6 1.530(3) . ?
C5 H5 0.9800 . ?
C6 H6 0.9800 . ?
C7 C12 1.371(4) . ?
C7 C8 1.389(4) . ?
C8 C9 1.368(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.386(3) . ?
C13 C18 1.387(3) . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C13 109.80(19) . . ?
O1 C1 C6 104.02(19) . . ?
C13 C1 C6 116.68(19) . . ?
O1 C1 H1 108.7 . . ?
C13 C1 H1 108.7 . . ?
C6 C1 H1 108.7 . . ?
O1 C2 C3 106.8(2) . . ?
O1 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 114.9(2) . . ?
C2 C3 C6 104.02(19) . . ?
C4 C3 C6 104.1(2) . . ?
C2 C3 H3 111.1 . . ?
C4 C3 H3 111.1 . . ?
C6 C3 H3 111.1 . . ?
O2 C4 C3 107.1(2) . . ?
O2 C4 H4A 110.3 . . ?
C3 C4 H4A 110.3 . . ?
O2 C4 H4B 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
O2 C5 C7 108.61(19) . . ?
O2 C5 C6 104.3(2) . . ?
C7 C5 C6 116.0(2) . . ?
O2 C5 H5 109.2 . . ?
C7 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C5 C6 C1 115.4(2) . . ?
C5 C6 C3 103.21(19) . . ?
C1 C6 C3 103.14(18) . . ?
C5 C6 H6 111.5 . . ?
C1 C6 H6 111.5 . . ?
C3 C6 H6 111.5 . . ?
C12 C7 C8 118.4(2) . . ?
C12 C7 C5 121.1(2) . . ?
C8 C7 C5 120.5(2) . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C18 116.9(2) . . ?
C14 C13 C1 121.4(2) . . ?
C18 C13 C1 121.7(2) . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 122.2(2) . . ?
C17 C18 Br1 117.2(2) . . ?
C13 C18 Br1 120.55(18) . . ?
C2 O1 C1 105.83(19) . . ?
C4 O2 C5 106.04(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 99.6(3) . . . . ?
O1 C2 C3 C6 -13.5(3) . . . . ?
C2 C3 C4 O2 -125.8(3) . . . . ?
C6 C3 C4 O2 -12.7(3) . . . . ?
O2 C5 C6 C1 142.6(2) . . . . ?
C7 C5 C6 C1 -98.0(3) . . . . ?
O2 C5 C6 C3 30.9(2) . . . . ?
C7 C5 C6 C3 150.3(2) . . . . ?
O1 C1 C6 C5 -80.2(2) . . . . ?
C13 C1 C6 C5 40.9(3) . . . . ?
O1 C1 C6 C3 31.6(2) . . . . ?
C13 C1 C6 C3 152.6(2) . . . . ?
C2 C3 C6 C5 109.7(2) . . . . ?
C4 C3 C6 C5 -10.9(3) . . . . ?
C2 C3 C6 C1 -10.8(3) . . . . ?
C4 C3 C6 C1 -131.4(2) . . . . ?
O2 C5 C7 C12 -134.9(2) . . . . ?
C6 C5 C7 C12 108.0(3) . . . . ?
O2 C5 C7 C8 45.9(3) . . . . ?
C6 C5 C7 C8 -71.2(3) . . . . ?
C12 C7 C8 C9 -0.9(4) . . . . ?
C5 C7 C8 C9 178.2(3) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C8 C7 C12 C11 1.3(4) . . . . ?
C5 C7 C12 C11 -177.8(2) . . . . ?
C10 C11 C12 C7 -1.0(5) . . . . ?
O1 C1 C13 C14 14.9(3) . . . . ?
C6 C1 C13 C14 -103.1(3) . . . . ?
O1 C1 C13 C18 -166.0(2) . . . . ?
C6 C1 C13 C18 76.1(3) . . . . ?
C18 C13 C14 C15 1.0(4) . . . . ?
C1 C13 C14 C15 -179.9(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 1.5(4) . . . . ?
C16 C17 C18 C13 -1.0(4) . . . . ?
C16 C17 C18 Br1 -179.7(2) . . . . ?
C14 C13 C18 C17 -0.2(4) . . . . ?
C1 C13 C18 C17 -179.4(2) . . . . ?
C14 C13 C18 Br1 178.40(17) . . . . ?
C1 C13 C18 Br1 -0.8(3) . . . . ?
C3 C2 O1 C1 34.8(3) . . . . ?
C13 C1 O1 C2 -167.2(2) . . . . ?
C6 C1 O1 C2 -41.6(2) . . . . ?
C3 C4 O2 C5 33.4(3) . . . . ?
C7 C5 O2 C4 -164.7(2) . . . . ?
C6 C5 O2 C4 -40.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 943366'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ar61m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(1R,4aS,8S,8aS)-1-(2-bromophenyl)-8-phenyl-octahydropyrano[3,4-c]pyran
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 Br O2'
_chemical_formula_sum            'C20 H21 Br O2'
_chemical_formula_weight         373.28
_chemical_absolute_configuration ad

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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   11.2110(12)
_cell_length_b                   16.7616(18)
_cell_length_c                   18.3398(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3446.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6522
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      23.44

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   'SABABS; Bruker,2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31390
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6049
_reflns_number_gt                5025
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0577P)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    mixed
_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   0.080(8)
_refine_ls_number_reflns         6049
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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
Br1A Br 0.67612(4) 0.06633(3) 0.80749(3) 0.07733(15) Uani 1 1 d . . .
C1A C 0.5089(3) 0.00541(18) 0.67574(17) 0.0391(7) Uani 1 1 d . . .
H1A H 0.5867 -0.0107 0.6952 0.047 Uiso 1 1 calc R . .
C2A C 0.4766(4) -0.1310(2) 0.6472(2) 0.0606(10) Uani 1 1 d . . .
H2A H 0.4223 -0.1755 0.6540 0.073 Uiso 1 1 calc R . .
H2B H 0.5520 -0.1448 0.6699 0.073 Uiso 1 1 calc R . .
C3A C 0.4958(4) -0.1172(2) 0.5667(2) 0.0539(9) Uani 1 1 d . . .
H3A H 0.4197 -0.1079 0.5430 0.065 Uiso 1 1 calc R . .
H3B H 0.5319 -0.1640 0.5449 0.065 Uiso 1 1 calc R . .
C4A C 0.5770(3) -0.04497(18) 0.55552(17) 0.0423(7) Uani 1 1 d . . .
H4A H 0.6536 -0.0573 0.5786 0.051 Uiso 1 1 calc R . .
C5A C 0.6019(4) -0.0270(2) 0.47612(18) 0.0551(9) Uani 1 1 d . . .
H5A H 0.5279 -0.0153 0.4510 0.066 Uiso 1 1 calc R . .
H5B H 0.6383 -0.0731 0.4530 0.066 Uiso 1 1 calc R . .
C6A C 0.6855(4) 0.0442(2) 0.47106(18) 0.0566(9) Uani 1 1 d . . .
H6A H 0.7605 0.0317 0.4948 0.068 Uiso 1 1 calc R . .
H6B H 0.7019 0.0561 0.4203 0.068 Uiso 1 1 calc R . .
C7A C 0.6053(3) 0.10162(19) 0.58243(17) 0.0420(7) Uani 1 1 d . . .
H7A H 0.6804 0.0935 0.6087 0.050 Uiso 1 1 calc R . .
C8A C 0.5251(3) 0.02834(18) 0.59499(16) 0.0385(7) Uani 1 1 d . . .
H8A H 0.4463 0.0397 0.5743 0.046 Uiso 1 1 calc R . .
C9A C 0.5544(3) 0.1813(2) 0.60438(19) 0.0509(9) Uani 1 1 d . . .
C10A C 0.4476(4) 0.2088(2) 0.5752(2) 0.0687(11) Uani 1 1 d . . .
H10A H 0.4053 0.1768 0.5428 0.082 Uiso 1 1 calc R . .
C11A C 0.4037(6) 0.2831(3) 0.5935(3) 0.0951(18) Uani 1 1 d . . .
H11A H 0.3322 0.3006 0.5734 0.114 Uiso 1 1 calc R . .
C12A C 0.4637(8) 0.3307(3) 0.6405(4) 0.107(2) Uani 1 1 d . . .
H12A H 0.4328 0.3803 0.6532 0.129 Uiso 1 1 calc R . .
C13A C 0.5712(7) 0.3055(3) 0.6697(3) 0.100(2) Uani 1 1 d . . .
H13A H 0.6128 0.3388 0.7013 0.120 Uiso 1 1 calc R . .
C14A C 0.6176(5) 0.2312(2) 0.6524(2) 0.0694(12) Uani 1 1 d . . .
H14A H 0.6897 0.2145 0.6723 0.083 Uiso 1 1 calc R . .
C15A C 0.4569(3) 0.06835(19) 0.72592(16) 0.0389(7) Uani 1 1 d . . .
C16A C 0.3413(3) 0.0941(2) 0.71568(18) 0.0501(8) Uani 1 1 d . . .
H16A H 0.2977 0.0733 0.6770 0.060 Uiso 1 1 calc R . .
C17A C 0.2876(3) 0.1499(2) 0.7608(2) 0.0571(9) Uani 1 1 d . . .
H17A H 0.2094 0.1658 0.7523 0.069 Uiso 1 1 calc R . .
C18A C 0.3505(4) 0.1812(2) 0.8179(2) 0.0592(10) Uani 1 1 d . . .
H18A H 0.3155 0.2190 0.8482 0.071 Uiso 1 1 calc R . .
C19A C 0.4667(4) 0.1563(2) 0.83064(19) 0.0568(10) Uani 1 1 d . . .
H19A H 0.5102 0.1772 0.8694 0.068 Uiso 1 1 calc R . .
C20A C 0.5167(3) 0.10017(19) 0.78498(17) 0.0447(8) Uani 1 1 d . . .
O1A O 0.4286(2) -0.06153(13) 0.68155(13) 0.0528(6) Uani 1 1 d . . .
O2A O 0.6322(2) 0.11234(14) 0.50534(12) 0.0554(6) Uani 1 1 d . . .
Br1B Br 1.16729(4) 0.30596(2) 0.98899(2) 0.06255(12) Uani 1 1 d . . .
C1B C 0.9390(3) 0.4229(2) 0.95936(18) 0.0474(8) Uani 1 1 d . . .
H1B H 1.0089 0.4263 0.9914 0.057 Uiso 1 1 calc R . .
C2B C 0.8218(5) 0.4800(2) 1.0548(2) 0.0713(11) Uani 1 1 d . . .
H2C H 0.8895 0.4801 1.0878 0.086 Uiso 1 1 calc R . .
H2D H 0.7501 0.4722 1.0835 0.086 Uiso 1 1 calc R . .
C3B C 0.8151(3) 0.5595(2) 1.0156(2) 0.0593(9) Uani 1 1 d . . .
H3C H 0.7428 0.5618 0.9866 0.071 Uiso 1 1 calc R . .
H3D H 0.8123 0.6025 1.0510 0.071 Uiso 1 1 calc R . .
C4B C 0.9218(3) 0.5700(2) 0.96697(18) 0.0518(9) Uani 1 1 d . . .
H4B H 0.9923 0.5683 0.9985 0.062 Uiso 1 1 calc R . .
C5B C 0.9256(4) 0.6496(2) 0.9267(2) 0.0644(10) Uani 1 1 d . . .
H5C H 0.8541 0.6556 0.8975 0.077 Uiso 1 1 calc R . .
H5D H 0.9281 0.6929 0.9617 0.077 Uiso 1 1 calc R . .
C6B C 1.0333(5) 0.6535(3) 0.8784(3) 0.0831(14) Uani 1 1 d . . .
H6C H 1.0340 0.7040 0.8526 0.100 Uiso 1 1 calc R . .
H6D H 1.1049 0.6507 0.9080 0.100 Uiso 1 1 calc R . .
C7B C 1.0365(3) 0.5109(2) 0.8595(2) 0.0537(9) Uani 1 1 d . . .
H7B H 1.1119 0.5050 0.8861 0.064 Uiso 1 1 calc R . .
C8B C 0.9327(3) 0.49926(19) 0.91325(19) 0.0462(8) Uani 1 1 d . . .
H8B H 0.8588 0.4971 0.8847 0.055 Uiso 1 1 calc R . .
C9B C 1.0385(3) 0.4563(2) 0.7947(2) 0.0543(9) Uani 1 1 d . . .
C10B C 0.9504(5) 0.4588(3) 0.7418(2) 0.0763(12) Uani 1 1 d . . .
H10B H 0.8859 0.4932 0.7477 0.092 Uiso 1 1 calc R . .
C11B C 0.9567(6) 0.4115(4) 0.6810(2) 0.0912(16) Uani 1 1 d . . .
H11B H 0.8974 0.4148 0.6457 0.109 Uiso 1 1 calc R . .
C12B C 1.0502(7) 0.3593(3) 0.6720(3) 0.103(2) Uani 1 1 d . . .
H12B H 1.0535 0.3266 0.6310 0.124 Uiso 1 1 calc R . .
C13B C 1.1372(6) 0.3556(3) 0.7229(3) 0.0863(17) Uani 1 1 d . . .
H13B H 1.2007 0.3206 0.7167 0.104 Uiso 1 1 calc R . .
C14B C 1.1322(4) 0.4033(2) 0.7839(2) 0.0636(11) Uani 1 1 d . . .
H14B H 1.1927 0.4001 0.8185 0.076 Uiso 1 1 calc R . .
C15B C 0.9446(3) 0.3443(2) 0.91791(17) 0.0460(8) Uani 1 1 d . . .
C16B C 0.8520(4) 0.3259(2) 0.8693(2) 0.0573(9) Uani 1 1 d . . .
H16B H 0.7897 0.3620 0.8631 0.069 Uiso 1 1 calc R . .
C17B C 0.8517(4) 0.2559(2) 0.8307(2) 0.0690(12) Uani 1 1 d . . .
H17B H 0.7892 0.2449 0.7989 0.083 Uiso 1 1 calc R . .
C18B C 0.9431(4) 0.2014(2) 0.8384(2) 0.0660(11) Uani 1 1 d . . .
H18B H 0.9426 0.1543 0.8116 0.079 Uiso 1 1 calc R . .
C19B C 1.0353(4) 0.2171(2) 0.8861(2) 0.0553(9) Uani 1 1 d . . .
H19B H 1.0969 0.1806 0.8921 0.066 Uiso 1 1 calc R . .
C20B C 1.0348(3) 0.28853(19) 0.92512(17) 0.0452(8) Uani 1 1 d . . .
O1B O 0.8341(3) 0.41590(14) 1.00394(13) 0.0631(6) Uani 1 1 d . . .
O2B O 1.0333(3) 0.58915(15) 0.82670(16) 0.0769(9) 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
Br1A C20A 1.920(4) . ?
C1A O1A 1.442(4) . ?
C1A C15A 1.517(4) . ?
C1A C8A 1.541(4) . ?
C1A H1A 0.9800 . ?
C2A O1A 1.430(4) . ?
C2A C3A 1.510(6) . ?
C2A H2A 0.9700 . ?
C2A H2B 0.9700 . ?
C3A C4A 1.528(5) . ?
C3A H3A 0.9700 . ?
C3A H3B 0.9700 . ?
C4A C5A 1.513(5) . ?
C4A C8A 1.540(4) . ?
C4A H4A 0.9800 . ?
C5A C6A 1.520(6) . ?
C5A H5A 0.9700 . ?
C5A H5B 0.9700 . ?
C6A O2A 1.434(4) . ?
C6A H6A 0.9700 . ?
C6A H6B 0.9700 . ?
C7A O2A 1.457(4) . ?
C7A C9A 1.508(5) . ?
C7A C8A 1.540(5) . ?
C7A H7A 0.9800 . ?
C8A H8A 0.9800 . ?
C9A C10A 1.390(6) . ?
C9A C14A 1.406(6) . ?
C10A C11A 1.380(6) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.354(9) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.384(9) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.387(7) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
C15A C16A 1.379(5) . ?
C15A C20A 1.381(4) . ?
C16A C17A 1.386(5) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.368(6) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.387(6) . ?
C18A H18A 0.9300 . ?
C19A C20A 1.379(5) . ?
C19A H19A 0.9300 . ?
Br1B C20B 1.914(4) . ?
C1B O1B 1.437(4) . ?
C1B C15B 1.523(5) . ?
C1B C8B 1.536(5) . ?
C1B H1B 0.9800 . ?
C2B O1B 1.430(4) . ?
C2B C3B 1.517(5) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4B 1.503(5) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C5B 1.524(5) . ?
C4B C8B 1.547(5) . ?
C4B H4B 0.9800 . ?
C5B C6B 1.499(7) . ?
C5B H5C 0.9700 . ?
C5B H5D 0.9700 . ?
C6B O2B 1.437(5) . ?
C6B H6C 0.9700 . ?
C6B H6D 0.9700 . ?
C7B O2B 1.443(4) . ?
C7B C9B 1.499(5) . ?
C7B C8B 1.538(5) . ?
C7B H7B 0.9800 . ?
C8B H8B 0.9800 . ?
C9B C10B 1.385(6) . ?
C9B C14B 1.391(5) . ?
C10B C11B 1.370(7) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.376(9) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.352(8) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.376(7) . ?
C13B H13B 0.9300 . ?
C14B H14B 0.9300 . ?
C15B C20B 1.384(5) . ?
C15B C16B 1.403(5) . ?
C16B C17B 1.371(5) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.380(6) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.378(6) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.395(5) . ?
C19B H19B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A C1A C15A 104.9(2) . . ?
O1A C1A C8A 109.8(2) . . ?
C15A C1A C8A 117.1(2) . . ?
O1A C1A H1A 108.3 . . ?
C15A C1A H1A 108.3 . . ?
C8A C1A H1A 108.3 . . ?
O1A C2A C3A 111.0(3) . . ?
O1A C2A H2A 109.4 . . ?
C3A C2A H2A 109.4 . . ?
O1A C2A H2B 109.4 . . ?
C3A C2A H2B 109.4 . . ?
H2A C2A H2B 108.0 . . ?
C2A C3A C4A 109.8(3) . . ?
C2A C3A H3A 109.7 . . ?
C4A C3A H3A 109.7 . . ?
C2A C3A H3B 109.7 . . ?
C4A C3A H3B 109.7 . . ?
H3A C3A H3B 108.2 . . ?
C5A C4A C3A 113.4(3) . . ?
C5A C4A C8A 111.3(3) . . ?
C3A C4A C8A 110.1(3) . . ?
C5A C4A H4A 107.2 . . ?
C3A C4A H4A 107.2 . . ?
C8A C4A H4A 107.2 . . ?
C4A C5A C6A 109.2(3) . . ?
C4A C5A H5A 109.8 . . ?
C6A C5A H5A 109.8 . . ?
C4A C5A H5B 109.8 . . ?
C6A C5A H5B 109.8 . . ?
H5A C5A H5B 108.3 . . ?
O2A C6A C5A 110.0(3) . . ?
O2A C6A H6A 109.7 . . ?
C5A C6A H6A 109.7 . . ?
O2A C6A H6B 109.7 . . ?
C5A C6A H6B 109.7 . . ?
H6A C6A H6B 108.2 . . ?
O2A C7A C9A 103.2(3) . . ?
O2A C7A C8A 111.4(3) . . ?
C9A C7A C8A 116.5(3) . . ?
O2A C7A H7A 108.5 . . ?
C9A C7A H7A 108.5 . . ?
C8A C7A H7A 108.5 . . ?
C7A C8A C4A 110.2(3) . . ?
C7A C8A C1A 114.3(3) . . ?
C4A C8A C1A 107.3(2) . . ?
C7A C8A H8A 108.3 . . ?
C4A C8A H8A 108.3 . . ?
C1A C8A H8A 108.3 . . ?
C10A C9A C14A 118.6(4) . . ?
C10A C9A C7A 121.1(4) . . ?
C14A C9A C7A 120.2(4) . . ?
C11A C10A C9A 120.8(5) . . ?
C11A C10A H10A 119.6 . . ?
C9A C10A H10A 119.6 . . ?
C12A C11A C10A 120.6(6) . . ?
C12A C11A H11A 119.7 . . ?
C10A C11A H11A 119.7 . . ?
C11A C12A C13A 119.9(5) . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A C14A 120.8(6) . . ?
C12A C13A H13A 119.6 . . ?
C14A C13A H13A 119.6 . . ?
C13A C14A C9A 119.2(5) . . ?
C13A C14A H14A 120.4 . . ?
C9A C14A H14A 120.4 . . ?
C16A C15A C20A 116.2(3) . . ?
C16A C15A C1A 119.8(3) . . ?
C20A C15A C1A 123.9(3) . . ?
C15A C16A C17A 122.6(3) . . ?
C15A C16A H16A 118.7 . . ?
C17A C16A H16A 118.7 . . ?
C18A C17A C16A 119.5(4) . . ?
C18A C17A H17A 120.3 . . ?
C16A C17A H17A 120.3 . . ?
C17A C18A C19A 119.8(3) . . ?
C17A C18A H18A 120.1 . . ?
C19A C18A H18A 120.1 . . ?
C20A C19A C18A 119.0(3) . . ?
C20A C19A H19A 120.5 . . ?
C18A C19A H19A 120.5 . . ?
C19A C20A C15A 122.9(3) . . ?
C19A C20A Br1A 116.7(3) . . ?
C15A C20A Br1A 120.4(3) . . ?
C2A O1A C1A 111.5(3) . . ?
C6A O2A C7A 114.4(2) . . ?
O1B C1B C15B 104.3(3) . . ?
O1B C1B C8B 110.1(3) . . ?
C15B C1B C8B 116.6(3) . . ?
O1B C1B H1B 108.5 . . ?
C15B C1B H1B 108.5 . . ?
C8B C1B H1B 108.5 . . ?
O1B C2B C3B 110.8(3) . . ?
O1B C2B H2C 109.5 . . ?
C3B C2B H2C 109.5 . . ?
O1B C2B H2D 109.5 . . ?
C3B C2B H2D 109.5 . . ?
H2C C2B H2D 108.1 . . ?
C4B C3B C2B 110.2(3) . . ?
C4B C3B H3C 109.6 . . ?
C2B C3B H3C 109.6 . . ?
C4B C3B H3D 109.6 . . ?
C2B C3B H3D 109.6 . . ?
H3C C3B H3D 108.1 . . ?
C3B C4B C5B 114.3(3) . . ?
C3B C4B C8B 110.5(3) . . ?
C5B C4B C8B 111.1(3) . . ?
C3B C4B H4B 106.8 . . ?
C5B C4B H4B 106.8 . . ?
C8B C4B H4B 106.8 . . ?
C6B C5B C4B 110.3(3) . . ?
C6B C5B H5C 109.6 . . ?
C4B C5B H5C 109.6 . . ?
C6B C5B H5D 109.6 . . ?
C4B C5B H5D 109.6 . . ?
H5C C5B H5D 108.1 . . ?
O2B C6B C5B 110.9(4) . . ?
O2B C6B H6C 109.5 . . ?
C5B C6B H6C 109.5 . . ?
O2B C6B H6D 109.5 . . ?
C5B C6B H6D 109.5 . . ?
H6C C6B H6D 108.0 . . ?
O2B C7B C9B 103.0(3) . . ?
O2B C7B C8B 111.3(3) . . ?
C9B C7B C8B 116.2(3) . . ?
O2B C7B H7B 108.7 . . ?
C9B C7B H7B 108.7 . . ?
C8B C7B H7B 108.7 . . ?
C1B C8B C7B 115.1(3) . . ?
C1B C8B C4B 107.0(3) . . ?
C7B C8B C4B 111.7(3) . . ?
C1B C8B H8B 107.6 . . ?
C7B C8B H8B 107.6 . . ?
C4B C8B H8B 107.6 . . ?
C10B C9B C14B 117.3(4) . . ?
C10B C9B C7B 121.8(4) . . ?
C14B C9B C7B 120.9(4) . . ?
C11B C10B C9B 121.1(5) . . ?
C11B C10B H10B 119.5 . . ?
C9B C10B H10B 119.5 . . ?
C10B C11B C12B 120.4(5) . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B H11B 119.8 . . ?
C13B C12B C11B 119.7(5) . . ?
C13B C12B H12B 120.2 . . ?
C11B C12B H12B 120.2 . . ?
C12B C13B C14B 120.4(5) . . ?
C12B C13B H13B 119.8 . . ?
C14B C13B H13B 119.8 . . ?
C13B C14B C9B 121.2(5) . . ?
C13B C14B H14B 119.4 . . ?
C9B C14B H14B 119.4 . . ?
C20B C15B C16B 117.0(3) . . ?
C20B C15B C1B 124.5(3) . . ?
C16B C15B C1B 118.5(3) . . ?
C17B C16B C15B 121.2(4) . . ?
C17B C16B H16B 119.4 . . ?
C15B C16B H16B 119.4 . . ?
C16B C17B C18B 120.8(4) . . ?
C16B C17B H17B 119.6 . . ?
C18B C17B H17B 119.6 . . ?
C19B C18B C17B 119.7(3) . . ?
C19B C18B H18B 120.2 . . ?
C17B C18B H18B 120.2 . . ?
C18B C19B C20B 119.1(4) . . ?
C18B C19B H19B 120.4 . . ?
C20B C19B H19B 120.4 . . ?
C15B C20B C19B 122.2(3) . . ?
C15B C20B Br1B 121.5(2) . . ?
C19B C20B Br1B 116.3(3) . . ?
C2B O1B C1B 112.9(3) . . ?
C6B O2B C7B 114.0(3) . . ?

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
O1A C2A C3A C4A 56.6(4) . . . . ?
C2A C3A C4A C5A 179.5(3) . . . . ?
C2A C3A C4A C8A -55.0(4) . . . . ?
C3A C4A C5A C6A -178.6(3) . . . . ?
C8A C4A C5A C6A 56.6(4) . . . . ?
C4A C5A C6A O2A -59.3(4) . . . . ?
O2A C7A C8A C4A 50.0(3) . . . . ?
C9A C7A C8A C4A 167.9(3) . . . . ?
O2A C7A C8A C1A 170.9(3) . . . . ?
C9A C7A C8A C1A -71.2(4) . . . . ?
C5A C4A C8A C7A -52.2(4) . . . . ?
C3A C4A C8A C7A -178.8(3) . . . . ?
C5A C4A C8A C1A -177.2(3) . . . . ?
C3A C4A C8A C1A 56.2(3) . . . . ?
O1A C1A C8A C7A 177.6(2) . . . . ?
C15A C1A C8A C7A 58.3(4) . . . . ?
O1A C1A C8A C4A -59.9(3) . . . . ?
C15A C1A C8A C4A -179.2(3) . . . . ?
O2A C7A C9A C10A 64.8(4) . . . . ?
C8A C7A C9A C10A -57.6(4) . . . . ?
O2A C7A C9A C14A -112.0(3) . . . . ?
C8A C7A C9A C14A 125.6(3) . . . . ?
C14A C9A C10A C11A -0.8(6) . . . . ?
C7A C9A C10A C11A -177.7(4) . . . . ?
C9A C10A C11A C12A -0.1(7) . . . . ?
C10A C11A C12A C13A 1.1(7) . . . . ?
C11A C12A C13A C14A -1.2(7) . . . . ?
C12A C13A C14A C9A 0.3(6) . . . . ?
C10A C9A C14A C13A 0.7(5) . . . . ?
C7A C9A C14A C13A 177.6(3) . . . . ?
O1A C1A C15A C16A -56.8(4) . . . . ?
C8A C1A C15A C16A 65.1(4) . . . . ?
O1A C1A C15A C20A 120.1(3) . . . . ?
C8A C1A C15A C20A -118.0(3) . . . . ?
C20A C15A C16A C17A 1.1(5) . . . . ?
C1A C15A C16A C17A 178.2(3) . . . . ?
C15A C16A C17A C18A 0.1(5) . . . . ?
C16A C17A C18A C19A -0.7(5) . . . . ?
C17A C18A C19A C20A 0.0(5) . . . . ?
C18A C19A C20A C15A 1.3(5) . . . . ?
C18A C19A C20A Br1A -178.2(3) . . . . ?
C16A C15A C20A C19A -1.8(5) . . . . ?
C1A C15A C20A C19A -178.8(3) . . . . ?
C16A C15A C20A Br1A 177.7(2) . . . . ?
C1A C15A C20A Br1A 0.7(4) . . . . ?
C3A C2A O1A C1A -61.7(4) . . . . ?
C15A C1A O1A C2A -169.8(3) . . . . ?
C8A C1A O1A C2A 63.7(3) . . . . ?
C5A C6A O2A C7A 60.2(4) . . . . ?
C9A C7A O2A C6A 178.6(3) . . . . ?
C8A C7A O2A C6A -55.8(4) . . . . ?
O1B C2B C3B C4B -55.4(5) . . . . ?
C2B C3B C4B C5B -178.1(3) . . . . ?
C2B C3B C4B C8B 55.6(4) . . . . ?
C3B C4B C5B C6B -178.6(3) . . . . ?
C8B C4B C5B C6B -52.6(4) . . . . ?
C4B C5B C6B O2B 58.2(5) . . . . ?
O1B C1B C8B C7B -176.4(3) . . . . ?
C15B C1B C8B C7B -57.9(4) . . . . ?
O1B C1B C8B C4B 58.9(3) . . . . ?
C15B C1B C8B C4B 177.4(3) . . . . ?
O2B C7B C8B C1B -171.2(3) . . . . ?
C9B C7B C8B C1B 71.4(4) . . . . ?
O2B C7B C8B C4B -49.0(4) . . . . ?
C9B C7B C8B C4B -166.4(3) . . . . ?
C3B C4B C8B C1B -56.9(4) . . . . ?
C5B C4B C8B C1B 175.1(3) . . . . ?
C3B C4B C8B C7B 176.4(3) . . . . ?
C5B C4B C8B C7B 48.3(4) . . . . ?
O2B C7B C9B C10B -56.7(5) . . . . ?
C8B C7B C9B C10B 65.3(5) . . . . ?
O2B C7B C9B C14B 120.5(4) . . . . ?
C8B C7B C9B C14B -117.5(4) . . . . ?
C14B C9B C10B C11B -0.8(7) . . . . ?
C7B C9B C10B C11B 176.5(4) . . . . ?
C9B C10B C11B C12B 1.2(8) . . . . ?
C10B C11B C12B C13B -1.0(8) . . . . ?
C11B C12B C13B C14B 0.5(7) . . . . ?
C12B C13B C14B C9B -0.1(6) . . . . ?
C10B C9B C14B C13B 0.2(6) . . . . ?
C7B C9B C14B C13B -177.1(3) . . . . ?
O1B C1B C15B C20B -115.9(3) . . . . ?
C8B C1B C15B C20B 122.5(4) . . . . ?
O1B C1B C15B C16B 63.6(4) . . . . ?
C8B C1B C15B C16B -58.0(4) . . . . ?
C20B C15B C16B C17B -0.1(5) . . . . ?
C1B C15B C16B C17B -179.7(4) . . . . ?
C15B C16B C17B C18B -0.3(6) . . . . ?
C16B C17B C18B C19B 0.7(6) . . . . ?
C17B C18B C19B C20B -0.7(5) . . . . ?
C16B C15B C20B C19B 0.2(5) . . . . ?
C1B C15B C20B C19B 179.7(3) . . . . ?
C16B C15B C20B Br1B 179.5(3) . . . . ?
C1B C15B C20B Br1B -0.9(4) . . . . ?
C18B C19B C20B C15B 0.2(5) . . . . ?
C18B C19B C20B Br1B -179.2(3) . . . . ?
C3B C2B O1B C1B 59.4(5) . . . . ?
C15B C1B O1B C2B 172.1(3) . . . . ?
C8B C1B O1B C2B -62.1(4) . . . . ?
C5B C6B O2B C7B -61.1(5) . . . . ?
C9B C7B O2B C6B -178.8(4) . . . . ?
C8B C7B O2B C6B 56.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 943367'
