# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
E.Stastna
N.P.Rath
D.F.Covey
_publ_contact_author_name        'Nigam P. Rath'
_publ_contact_author_email       rathn@umsl.edu

data_c23310
_database_code_depnum_ccdc_archive 'CCDC 814522'
#TrackingRef 'ent-2-derivative.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H31 Br O3'
_chemical_formula_sum            'C25 H31 Br O3'
_chemical_formula_weight         459.41

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   P2(1)2(1)2(1)

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                   10.3869(6)
_cell_length_b                   13.1736(7)
_cell_length_c                   15.8519(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2169.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      29.06

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      no
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    1.919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_T_max  0.6910
_exptl_absorpt_process_details   'sadabs v2008/1'

_exptl_special_details           
;
All H atoms were located and refined.
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            104988
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         31.10
_reflns_number_total             6969
_reflns_number_gt                6568
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Shelx restraints used:
sadi 0.005 c1 h1a c1 h1b
sadi 0.005 c3 h3a c3 h3b
sadi 0.005 c4 h4a c4 h4b
sadi 0.005 c5 h5a c5 h5b
sadi 0.005 c6 h6a c6 h6b
sadi 0.005 c7 h7a c7 h7b
sadi 0.005 c9 h9a c9 h9b
sadi 0.005 c10 h10a c10 h10b
sadi 0.005 c11 h11a c11 h11b
sadi 0.005 c12 h12a c12 h12b
sadi 0.003 c3' h3' c4' h4' c6' h6' c7' h7'

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.2191P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_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   -0.007(3)
_refine_ls_number_reflns         6969
_refine_ls_number_parameters     386
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0500
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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 1.097038(12) 0.976640(9) 0.867845(8) 0.02471(3) Uani 1 1 d . . .
O1 O 0.96682(13) 0.59468(8) -0.07259(6) 0.0360(3) Uani 1 1 d . . .
O2 O 0.72422(8) 0.77183(7) 0.56205(5) 0.01753(16) Uani 1 1 d . . .
O3 O 0.68002(9) 0.65679(7) 0.66324(5) 0.02027(16) Uani 1 1 d . . .
C1 C 0.87665(12) 0.69982(9) 0.03451(7) 0.0217(2) Uani 1 1 d D . .
C2 C 0.95172(13) 0.61052(9) 0.00219(7) 0.0222(2) Uani 1 1 d . . .
C3 C 1.01253(14) 0.54531(9) 0.06886(8) 0.0237(2) Uani 1 1 d D . .
C4 C 1.09455(13) 0.61221(10) 0.12697(7) 0.0244(2) Uani 1 1 d D . .
C5 C 0.96249(12) 0.59743(10) 0.29626(7) 0.0228(2) Uani 1 1 d D . .
C6 C 0.85745(12) 0.56903(9) 0.35867(8) 0.0214(2) Uani 1 1 d D . .
C7 C 0.69445(11) 0.63259(9) 0.46226(7) 0.01672(19) Uani 1 1 d D . .
C8 C 0.63203(10) 0.72274(9) 0.50548(7) 0.0165(2) Uani 1 1 d . . .
C9 C 0.59052(12) 0.80350(9) 0.44348(7) 0.01846(19) Uani 1 1 d D . .
C10 C 0.69509(11) 0.83106(9) 0.37957(7) 0.0176(2) Uani 1 1 d D . .
C11 C 0.79064(14) 0.82828(9) 0.19599(8) 0.0237(2) Uani 1 1 d D . .
C12 C 0.88835(16) 0.85606(9) 0.12799(9) 0.0301(3) Uani 1 1 d D . .
C4A C 1.01747(11) 0.70032(9) 0.16493(7) 0.0194(2) Uani 1 1 d . . .
C4B C 0.91198(11) 0.66859(8) 0.22836(6) 0.01588(18) Uani 1 1 d . . .
C6A C 0.79969(10) 0.66270(9) 0.39981(7) 0.01546(19) Uani 1 1 d . . .
C10A C 0.74741(10) 0.73717(8) 0.33393(7) 0.01447(18) Uani 1 1 d . . .
C10B C 0.84879(11) 0.76385(9) 0.26649(7) 0.0166(2) Uani 1 1 d . . .
C12A C 0.96072(13) 0.76461(9) 0.09324(7) 0.0210(2) Uani 1 1 d . . .
C1' C 0.73507(10) 0.73224(8) 0.63967(7) 0.01583(18) Uani 1 1 d . . .
C2' C 0.82329(10) 0.79324(9) 0.69332(7) 0.01554(19) Uani 1 1 d . . .
C3' C 0.86141(11) 0.89093(9) 0.67115(7) 0.0176(2) Uani 1 1 d D . .
C4' C 0.94241(11) 0.94612(9) 0.72303(7) 0.0184(2) Uani 1 1 d D . .
C5' C 0.98492(11) 0.90195(9) 0.79733(7) 0.01677(19) Uani 1 1 d . . .
C6' C 0.94998(11) 0.80474(9) 0.82018(7) 0.0179(2) Uani 1 1 d D . .
C7' C 0.86777(11) 0.75010(9) 0.76836(7) 0.0173(2) Uani 1 1 d D . .
H4A H 1.1656(15) 0.6371(14) 0.0935(10) 0.034(5) Uiso 1 1 d D . .
H4B H 1.1351(17) 0.5734(13) 0.1714(10) 0.034(5) Uiso 1 1 d D . .
H3A H 1.0634(14) 0.4904(11) 0.0434(10) 0.027(4) Uiso 1 1 d D . .
H3B H 0.9460(16) 0.5108(14) 0.1024(11) 0.040(5) Uiso 1 1 d D . .
H1A H 0.8447(17) 0.7432(14) -0.0140(10) 0.033(5) Uiso 1 1 d D . .
H1B H 0.7987(15) 0.6733(14) 0.0660(11) 0.031(4) Uiso 1 1 d D . .
H12C H 1.0371(18) 0.7891(14) 0.0607(11) 0.030(5) Uiso 1 1 d . . .
H12A H 0.9528(15) 0.9007(13) 0.1517(10) 0.032(5) Uiso 1 1 d D . .
H12B H 0.8552(18) 0.8969(15) 0.0821(10) 0.043(6) Uiso 1 1 d D . .
H11A H 0.7216(15) 0.7906(12) 0.1711(10) 0.029(4) Uiso 1 1 d D . .
H11B H 0.7557(17) 0.8902(11) 0.2175(10) 0.033(5) Uiso 1 1 d D . .
H10D H 0.9212(18) 0.8040(14) 0.2947(11) 0.034(5) Uiso 1 1 d . . .
H4D H 0.8460(13) 0.6300(11) 0.1981(9) 0.011(3) Uiso 1 1 d . . .
H4C H 1.0800(16) 0.7420(12) 0.1953(10) 0.021(4) Uiso 1 1 d . . .
H5A H 1.0377(15) 0.6265(13) 0.3234(10) 0.032(4) Uiso 1 1 d D . .
H5B H 1.0020(18) 0.5384(11) 0.2706(11) 0.040(5) Uiso 1 1 d D . .
H6A H 0.8937(17) 0.5275(13) 0.4056(10) 0.039(5) Uiso 1 1 d D . .
H6B H 0.7856(14) 0.5340(13) 0.3287(10) 0.028(4) Uiso 1 1 d D . .
H6C H 0.8674(14) 0.7012(12) 0.4304(10) 0.017(4) Uiso 1 1 d . . .
H10C H 0.6774(15) 0.7033(12) 0.3054(10) 0.017(3) Uiso 1 1 d . . .
H10A H 0.6538(15) 0.8790(11) 0.3407(9) 0.020(4) Uiso 1 1 d D . .
H10B H 0.7653(14) 0.8674(13) 0.4079(10) 0.029(4) Uiso 1 1 d D . .
H9A H 0.5155(13) 0.7772(12) 0.4132(9) 0.022(4) Uiso 1 1 d D . .
H9B H 0.5639(16) 0.8640(10) 0.4746(10) 0.027(4) Uiso 1 1 d D . .
H8 H 0.5597(14) 0.7016(11) 0.5380(9) 0.012(3) Uiso 1 1 d . . .
H7A H 0.7264(15) 0.5905(11) 0.5026(9) 0.023(4) Uiso 1 1 d D . .
H7B H 0.6300(13) 0.5994(12) 0.4350(9) 0.020(4) Uiso 1 1 d D . .
H3' H 0.8277(15) 0.9199(12) 0.6215(7) 0.026(4) Uiso 1 1 d D . .
H4' H 0.9670(15) 1.0131(8) 0.7094(10) 0.027(4) Uiso 1 1 d D . .
H6' H 0.9820(14) 0.7749(11) 0.8701(7) 0.019(3) Uiso 1 1 d D . .
H7' H 0.8464(14) 0.6833(7) 0.7844(9) 0.016(3) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02207(5) 0.02342(5) 0.02864(6) -0.00835(5) -0.00753(5) 0.00345(5)
O1 0.0732(8) 0.0216(4) 0.0133(4) -0.0012(3) 0.0041(4) -0.0001(5)
O2 0.0196(4) 0.0218(4) 0.0111(3) -0.0004(3) -0.0003(3) -0.0010(3)
O3 0.0223(4) 0.0208(4) 0.0177(4) 0.0014(3) 0.0008(3) -0.0017(3)
C1 0.0299(7) 0.0209(5) 0.0142(5) 0.0026(4) 0.0014(4) -0.0019(4)
C2 0.0348(6) 0.0161(5) 0.0156(5) -0.0006(4) 0.0003(4) -0.0067(4)
C3 0.0365(7) 0.0175(5) 0.0173(5) -0.0016(4) 0.0035(5) 0.0013(5)
C4 0.0217(5) 0.0333(6) 0.0181(5) -0.0042(5) 0.0030(5) 0.0033(5)
C5 0.0233(6) 0.0295(6) 0.0156(5) 0.0006(5) 0.0011(4) 0.0113(5)
C6 0.0288(5) 0.0206(5) 0.0149(5) 0.0017(4) 0.0014(4) 0.0082(4)
C7 0.0180(5) 0.0185(5) 0.0137(4) 0.0002(4) -0.0006(4) 0.0003(4)
C8 0.0146(4) 0.0211(5) 0.0139(4) -0.0001(4) -0.0006(4) -0.0003(4)
C9 0.0160(5) 0.0234(5) 0.0161(4) -0.0002(4) 0.0006(4) 0.0034(5)
C10 0.0188(5) 0.0177(5) 0.0162(5) -0.0001(4) 0.0006(4) 0.0018(4)
C11 0.0335(6) 0.0172(5) 0.0203(5) 0.0041(4) 0.0084(5) 0.0049(5)
C12 0.0490(8) 0.0147(4) 0.0265(6) 0.0016(5) 0.0159(6) -0.0024(5)
C4A 0.0176(5) 0.0236(5) 0.0170(5) -0.0064(4) 0.0021(4) -0.0048(4)
C4B 0.0160(5) 0.0181(4) 0.0136(4) -0.0014(4) 0.0005(4) 0.0000(4)
C6A 0.0153(4) 0.0184(5) 0.0127(4) -0.0006(4) -0.0020(4) 0.0020(4)
C10A 0.0149(4) 0.0164(5) 0.0120(4) -0.0002(4) -0.0009(4) -0.0003(4)
C10B 0.0182(5) 0.0160(5) 0.0156(5) -0.0023(4) 0.0020(4) -0.0025(4)
C12A 0.0280(6) 0.0160(5) 0.0189(5) -0.0020(4) 0.0083(4) -0.0072(4)
C1' 0.0157(4) 0.0193(5) 0.0125(4) -0.0008(4) 0.0014(4) 0.0032(4)
C2' 0.0165(5) 0.0185(5) 0.0116(4) -0.0008(4) 0.0027(4) 0.0026(4)
C3' 0.0215(5) 0.0187(5) 0.0127(4) 0.0015(4) 0.0010(4) 0.0036(4)
C4' 0.0221(5) 0.0159(5) 0.0171(5) 0.0003(4) 0.0019(4) 0.0023(4)
C5' 0.0154(5) 0.0195(5) 0.0154(4) -0.0032(4) 0.0001(4) 0.0022(4)
C6' 0.0190(5) 0.0225(5) 0.0121(4) 0.0023(4) 0.0009(4) 0.0026(4)
C7' 0.0199(5) 0.0183(5) 0.0137(4) 0.0027(4) 0.0031(4) 0.0010(4)

_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 C5' 1.8904(11) . ?
O1 C2 1.2137(15) . ?
O2 C1' 1.3410(13) . ?
O2 C8 1.4626(14) . ?
O3 C1' 1.2060(14) . ?
C1 C2 1.5014(18) . ?
C1 C12A 1.5355(17) . ?
C1 H1A 1.014(13) . ?
C1 H1B 1.013(13) . ?
C2 C3 1.5014(18) . ?
C3 C4 1.5334(18) . ?
C3 H3A 0.983(13) . ?
C3 H3B 0.983(13) . ?
C4 C4A 1.5331(17) . ?
C4 H4A 0.966(13) . ?
C4 H4B 0.966(13) . ?
C5 C6 1.5196(17) . ?
C5 C4B 1.5207(16) . ?
C5 H5A 0.970(12) . ?
C5 H5B 0.969(12) . ?
C6 C6A 1.5192(16) . ?
C6 H6A 0.997(13) . ?
C6 H6B 0.998(13) . ?
C7 C8 1.5165(16) . ?
C7 C6A 1.5272(16) . ?
C7 H7A 0.909(11) . ?
C7 H7B 0.909(11) . ?
C8 C9 1.5112(16) . ?
C8 H8 0.953(14) . ?
C9 C10 1.5291(16) . ?
C9 H9A 0.978(12) . ?
C9 H9B 0.977(12) . ?
C10 C10A 1.5325(15) . ?
C10 H10A 0.981(12) . ?
C10 H10B 0.982(12) . ?
C11 C12 1.5251(17) . ?
C11 C10B 1.5279(17) . ?
C11 H11A 0.958(12) . ?
C11 H11B 0.956(12) . ?
C12 C12A 1.5231(17) . ?
C12 H12A 0.967(13) . ?
C12 H12B 0.968(14) . ?
C4A C12A 1.5351(18) . ?
C4A C4B 1.5449(16) . ?
C4A H4C 0.977(16) . ?
C4B C10B 1.5397(15) . ?
C4B H4D 0.978(14) . ?
C6A C10A 1.5323(15) . ?
C6A H6C 0.993(16) . ?
C10A C10B 1.5413(15) . ?
C10A H10C 0.965(16) . ?
C10B H10D 1.022(18) . ?
C12A H12C 1.000(18) . ?
C1' C2' 1.4862(15) . ?
C2' C3' 1.3915(16) . ?
C2' C7' 1.3970(15) . ?
C3' C4' 1.3830(17) . ?
C3' H3' 0.943(8) . ?
C4' C5' 1.3860(16) . ?
C4' H4' 0.943(8) . ?
C5' C6' 1.3794(17) . ?
C6' C7' 1.3863(17) . ?
C6' H6' 0.944(8) . ?
C7' H7' 0.942(8) . ?

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
C1' O2 C8 116.47(9) . . ?
C2 C1 C12A 110.32(10) . . ?
C2 C1 H1A 110.7(11) . . ?
C12A C1 H1A 109.4(11) . . ?
C2 C1 H1B 108.3(11) . . ?
C12A C1 H1B 110.3(10) . . ?
H1A C1 H1B 107.9(15) . . ?
O1 C2 C1 122.36(12) . . ?
O1 C2 C3 122.32(12) . . ?
C1 C2 C3 115.25(10) . . ?
C2 C3 C4 109.13(10) . . ?
C2 C3 H3A 111.0(9) . . ?
C4 C3 H3A 111.8(9) . . ?
C2 C3 H3B 110.5(12) . . ?
C4 C3 H3B 109.4(11) . . ?
H3A C3 H3B 105.0(14) . . ?
C4A C4 C3 112.39(11) . . ?
C4A C4 H4A 111.0(12) . . ?
C3 C4 H4A 106.8(11) . . ?
C4A C4 H4B 110.0(11) . . ?
C3 C4 H4B 112.1(11) . . ?
H4A C4 H4B 104.3(15) . . ?
C6 C5 C4B 111.40(10) . . ?
C6 C5 H5A 112.7(10) . . ?
C4B C5 H5A 110.3(11) . . ?
C6 C5 H5B 112.3(11) . . ?
C4B C5 H5B 110.1(11) . . ?
H5A C5 H5B 99.3(15) . . ?
C6A C6 C5 111.29(10) . . ?
C6A C6 H6A 105.9(11) . . ?
C5 C6 H6A 110.5(11) . . ?
C6A C6 H6B 106.6(10) . . ?
C5 C6 H6B 109.9(10) . . ?
H6A C6 H6B 112.5(15) . . ?
C8 C7 C6A 113.29(10) . . ?
C8 C7 H7A 108.4(10) . . ?
C6A C7 H7A 110.7(11) . . ?
C8 C7 H7B 106.1(10) . . ?
C6A C7 H7B 110.1(10) . . ?
H7A C7 H7B 108.0(14) . . ?
O2 C8 C9 105.92(9) . . ?
O2 C8 C7 110.08(9) . . ?
C9 C8 C7 112.30(9) . . ?
O2 C8 H8 108.3(9) . . ?
C9 C8 H8 109.4(9) . . ?
C7 C8 H8 110.6(9) . . ?
C8 C9 C10 113.29(10) . . ?
C8 C9 H9A 107.3(9) . . ?
C10 C9 H9A 109.0(9) . . ?
C8 C9 H9B 109.1(10) . . ?
C10 C9 H9B 109.9(10) . . ?
H9A C9 H9B 108.1(13) . . ?
C9 C10 C10A 111.90(9) . . ?
C9 C10 H10A 105.0(9) . . ?
C10A C10 H10A 112.2(9) . . ?
C9 C10 H10B 109.9(10) . . ?
C10A C10 H10B 110.3(10) . . ?
H10A C10 H10B 107.4(14) . . ?
C12 C11 C10B 112.78(11) . . ?
C12 C11 H11A 109.4(11) . . ?
C10B C11 H11A 108.0(11) . . ?
C12 C11 H11B 107.4(11) . . ?
C10B C11 H11B 111.4(11) . . ?
H11A C11 H11B 107.7(15) . . ?
C12A C12 C11 113.22(10) . . ?
C12A C12 H12A 106.3(11) . . ?
C11 C12 H12A 109.3(10) . . ?
C12A C12 H12B 110.1(12) . . ?
C11 C12 H12B 115.3(12) . . ?
H12A C12 H12B 101.5(17) . . ?
C4 C4A C12A 109.13(9) . . ?
C4 C4A C4B 114.90(10) . . ?
C12A C4A C4B 111.03(10) . . ?
C4 C4A H4C 105.8(10) . . ?
C12A C4A H4C 108.0(9) . . ?
C4B C4A H4C 107.6(9) . . ?
C5 C4B C10B 111.82(9) . . ?
C5 C4B C4A 112.50(10) . . ?
C10B C4B C4A 109.71(9) . . ?
C5 C4B H4D 105.6(8) . . ?
C10B C4B H4D 108.5(8) . . ?
C4A C4B H4D 108.5(8) . . ?
C6 C6A C7 110.48(10) . . ?
C6 C6A C10A 111.55(9) . . ?
C7 C6A C10A 110.75(9) . . ?
C6 C6A H6C 110.2(9) . . ?
C7 C6A H6C 108.9(9) . . ?
C10A C6A H6C 104.8(9) . . ?
C6A C10A C10 108.70(9) . . ?
C6A C10A C10B 112.12(9) . . ?
C10 C10A C10B 112.68(9) . . ?
C6A C10A H10C 106.9(9) . . ?
C10 C10A H10C 109.1(9) . . ?
C10B C10A H10C 107.1(9) . . ?
C11 C10B C4B 109.52(9) . . ?
C11 C10B C10A 111.34(10) . . ?
C4B C10B C10A 112.19(9) . . ?
C11 C10B H10D 108.9(10) . . ?
C4B C10B H10D 106.2(10) . . ?
C10A C10B H10D 108.5(10) . . ?
C12 C12A C4A 110.99(10) . . ?
C12 C12A C1 112.24(12) . . ?
C4A C12A C1 111.13(10) . . ?
C12 C12A H12C 108.8(10) . . ?
C4A C12A H12C 104.8(10) . . ?
C1 C12A H12C 108.6(10) . . ?
O3 C1' O2 124.40(10) . . ?
O3 C1' C2' 124.10(10) . . ?
O2 C1' C2' 111.50(9) . . ?
C3' C2' C7' 119.81(10) . . ?
C3' C2' C1' 122.07(10) . . ?
C7' C2' C1' 118.11(10) . . ?
C4' C3' C2' 120.61(10) . . ?
C4' C3' H3' 120.6(11) . . ?
C2' C3' H3' 118.7(11) . . ?
C3' C4' C5' 118.58(11) . . ?
C3' C4' H4' 121.4(10) . . ?
C5' C4' H4' 120.0(10) . . ?
C6' C5' C4' 121.94(11) . . ?
C6' C5' Br1 119.35(9) . . ?
C4' C5' Br1 118.70(9) . . ?
C5' C6' C7' 119.25(10) . . ?
C5' C6' H6' 120.9(9) . . ?
C7' C6' H6' 119.8(9) . . ?
C6' C7' C2' 119.80(11) . . ?
C6' C7' H7' 118.1(9) . . ?
C2' C7' H7' 122.1(9) . . ?

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
C12A C1 C2 O1 -122.74(14) . . . . ?
C12A C1 C2 C3 54.21(14) . . . . ?
O1 C2 C3 C4 123.32(14) . . . . ?
C1 C2 C3 C4 -53.63(15) . . . . ?
C2 C3 C4 C4A 54.96(14) . . . . ?
C4B C5 C6 C6A -57.54(13) . . . . ?
C1' O2 C8 C9 153.76(9) . . . . ?
C1' O2 C8 C7 -84.61(11) . . . . ?
C6A C7 C8 O2 -68.10(11) . . . . ?
C6A C7 C8 C9 49.65(12) . . . . ?
O2 C8 C9 C10 72.05(11) . . . . ?
C7 C8 C9 C10 -48.15(13) . . . . ?
C8 C9 C10 C10A 53.26(12) . . . . ?
C10B C11 C12 C12A 51.92(16) . . . . ?
C3 C4 C4A C12A -57.78(13) . . . . ?
C3 C4 C4A C4B 67.65(13) . . . . ?
C6 C5 C4B C10B 54.94(14) . . . . ?
C6 C5 C4B C4A 178.94(10) . . . . ?
C4 C4A C4B C5 50.74(13) . . . . ?
C12A C4A C4B C5 175.18(10) . . . . ?
C4 C4A C4B C10B 175.90(10) . . . . ?
C12A C4A C4B C10B -59.66(12) . . . . ?
C5 C6 C6A C7 -179.99(9) . . . . ?
C5 C6 C6A C10A 56.35(13) . . . . ?
C8 C7 C6A C6 -179.74(9) . . . . ?
C8 C7 C6A C10A -55.62(12) . . . . ?
C6 C6A C10A C10 -178.07(10) . . . . ?
C7 C6A C10A C10 58.43(12) . . . . ?
C6 C6A C10A C10B -52.82(12) . . . . ?
C7 C6A C10A C10B -176.33(9) . . . . ?
C9 C10 C10A C6A -57.56(12) . . . . ?
C9 C10 C10A C10B 177.52(9) . . . . ?
C12 C11 C10B C4B -55.29(13) . . . . ?
C12 C11 C10B C10A -179.94(10) . . . . ?
C5 C4B C10B C11 -175.58(10) . . . . ?
C4A C4B C10B C11 58.87(12) . . . . ?
C5 C4B C10B C10A -51.42(13) . . . . ?
C4A C4B C10B C10A -176.97(9) . . . . ?
C6A C10A C10B C11 173.48(9) . . . . ?
C10 C10A C10B C11 -63.49(12) . . . . ?
C6A C10A C10B C4B 50.33(12) . . . . ?
C10 C10A C10B C4B 173.36(9) . . . . ?
C11 C12 C12A C4A -50.89(16) . . . . ?
C11 C12 C12A C1 74.14(15) . . . . ?
C4 C4A C12A C12 -177.36(10) . . . . ?
C4B C4A C12A C12 54.99(13) . . . . ?
C4 C4A C12A C1 56.99(13) . . . . ?
C4B C4A C12A C1 -70.66(12) . . . . ?
C2 C1 C12A C12 -179.75(10) . . . . ?
C2 C1 C12A C4A -54.80(12) . . . . ?
C8 O2 C1' O3 4.40(15) . . . . ?
C8 O2 C1' C2' -175.40(9) . . . . ?
O3 C1' C2' C3' -164.95(11) . . . . ?
O2 C1' C2' C3' 14.85(14) . . . . ?
O3 C1' C2' C7' 14.69(16) . . . . ?
O2 C1' C2' C7' -165.51(9) . . . . ?
C7' C2' C3' C4' -0.42(17) . . . . ?
C1' C2' C3' C4' 179.22(10) . . . . ?
C2' C3' C4' C5' 0.15(17) . . . . ?
C3' C4' C5' C6' 0.76(17) . . . . ?
C3' C4' C5' Br1 179.37(8) . . . . ?
C4' C5' C6' C7' -1.38(17) . . . . ?
Br1 C5' C6' C7' -179.98(8) . . . . ?
C5' C6' C7' C2' 1.08(16) . . . . ?
C3' C2' C7' C6' -0.21(16) . . . . ?
C1' C2' C7' C6' -179.86(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.045