#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150926.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150926
loop_
_publ_author_name
'Zezula, Josef'
'Singer, Lisa'
'Przybył, Anna K.'
'Hashimoto, Akihiro'
'Dersch, Christina M.'
'Rothman, Richard B.'
'Deschamps, Jeffrey'
'Lee, Yong Sok'
'Jacobson, Arthur E.'
'Rice, Kenner C.'
_publ_section_title
;
 Synthesis and pharmacological effects of the enantiomers of the
 N-phenethyl analogues of the ortho and para e- and f-oxide-bridged
 phenylmorphans
;
_journal_issue                   16
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2868
_journal_page_last               2883
_journal_paper_doi               10.1039/b803433h
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H19 N2 O3, C10 H14 Br O4 S'
_chemical_formula_sum            'C25 H33 Br N2 O7 S'
_chemical_formula_weight         585.50
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.719(3)
_cell_length_b                   13.922(5)
_cell_length_c                   24.899(12)
_cell_measurement_reflns_used    2099
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.76
_cell_volume                     2675.7(19)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001b)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001b)'
_computing_data_reduction
;
Bruker SAINT v6.45 (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001a)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000a)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18485
_diffrn_reflns_theta_full        28.51
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  variable
_diffrn_standards_number         1476
_exptl_absorpt_coefficient_mu    1.660
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000b)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.090(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.122
_refine_ls_shift/su_mean         0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                5322
_reflns_number_total             6212
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b803433h.txt
_cod_data_source_block           knih34
_cod_original_cell_volume        2675.7(18)
_cod_database_code               7150926
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'
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 1.0294(4) -0.0268(2) 0.09278(13) 0.0234(7) Uani 1 1 d . . .
H1A H 1.1267 0.0011 0.1142 0.028 Uiso 1 1 calc R . .
N2 N 1.1027(4) -0.10131(19) 0.05393(11) 0.0207(5) Uani 1 1 d . . .
H2 H 1.170(6) -0.065(3) 0.0291(16) 0.031 Uiso 1 1 d . . .
C2 C 1.2220(4) -0.1705(2) 0.08144(14) 0.0244(7) Uani 1 1 d . . .
H2A H 1.2895 -0.2056 0.0545 0.037 Uiso 1 1 calc R . .
H2B H 1.1538 -0.2161 0.1027 0.037 Uiso 1 1 calc R . .
H2C H 1.3008 -0.1351 0.1051 0.037 Uiso 1 1 calc R . .
C3 C 0.9614(4) -0.1505(2) 0.02275(12) 0.0200(6) Uani 1 1 d . . .
H3A H 0.8870 -0.1875 0.0477 0.024 Uiso 1 1 calc R . .
H3B H 1.0135 -0.1961 -0.0032 0.024 Uiso 1 1 calc R . .
C4 C 0.8509(4) -0.0769(2) -0.00758(13) 0.0204(6) Uani 1 1 d . . .
H4A H 0.7460 -0.1098 -0.0212 0.024 Uiso 1 1 calc R . .
H4B H 0.9174 -0.0542 -0.0391 0.024 Uiso 1 1 calc R . .
C4A C 0.7920(4) 0.0136(2) 0.02615(13) 0.0190(6) Uani 1 1 d . . .
C4B C 0.7796(4) 0.0975(2) -0.01335(13) 0.0206(6) Uani 1 1 d . . .
C5 C 0.6505(4) 0.1279(2) -0.04847(13) 0.0211(6) Uani 1 1 d . . .
H5A H 0.5379 0.1004 -0.0480 0.025 Uiso 1 1 calc R . .
C6 C 0.6955(5) 0.2020(2) -0.08486(13) 0.0217(6) Uani 1 1 d . . .
N6 N 0.5598(4) 0.24046(19) -0.12056(12) 0.0242(6) Uani 1 1 d . . .
O6A O 0.4061(3) 0.21624(17) -0.11149(11) 0.0313(6) Uani 1 1 d . . .
O6B O 0.6013(4) 0.29632(19) -0.15725(11) 0.0382(7) Uani 1 1 d . . .
C7 C 0.8614(5) 0.2421(2) -0.08840(14) 0.0259(7) Uani 1 1 d . . .
H7A H 0.8860 0.2900 -0.1145 0.031 Uiso 1 1 calc R . .
C8 C 0.9919(5) 0.2106(2) -0.05284(15) 0.0271(7) Uani 1 1 d . . .
H8A H 1.1059 0.2362 -0.0542 0.032 Uiso 1 1 calc R . .
C9 C 0.9463(4) 0.1405(2) -0.01572(14) 0.0232(7) Uani 1 1 d . . .
O9 O 1.0578(3) 0.10446(16) 0.02338(10) 0.0270(5) Uani 1 1 d . . .
C9A C 0.9432(5) 0.0530(2) 0.06083(14) 0.0241(7) Uani 1 1 d . . .
H9AA H 0.8946 0.1007 0.0868 0.029 Uiso 1 1 calc R . .
C10 C 0.6427(4) -0.0070(2) 0.06558(14) 0.0241(7) Uani 1 1 d . . .
H10A H 0.5423 -0.0332 0.0457 0.029 Uiso 1 1 calc R . .
H10B H 0.6060 0.0536 0.0830 0.029 Uiso 1 1 calc R . .
C11 C 0.7014(5) -0.0805(2) 0.10943(14) 0.0267(7) Uani 1 1 d . . .
H11A H 0.6186 -0.0773 0.1397 0.032 Uiso 1 1 calc R . .
H11B H 0.6941 -0.1459 0.0940 0.032 Uiso 1 1 calc R . .
C12 C 0.8883(5) -0.0653(3) 0.13201(14) 0.0295(8) Uani 1 1 d . . .
H12A H 0.8805 -0.0201 0.1626 0.035 Uiso 1 1 calc R . .
H12B H 0.9291 -0.1276 0.1465 0.035 Uiso 1 1 calc R . .
C1' C 0.3035(5) -0.0230(2) 0.26940(13) 0.0235(6) Uani 1 1 d . . .
C1A' C 0.1605(5) -0.0943(3) 0.25566(14) 0.0314(8) Uani 1 1 d . . .
H1AA H 0.2001 -0.1371 0.2269 0.047 Uiso 1 1 calc R . .
H1AB H 0.0573 -0.0593 0.2437 0.047 Uiso 1 1 calc R . .
H1AC H 0.1319 -0.1324 0.2876 0.047 Uiso 1 1 calc R . .
C2' C 0.3680(4) 0.0377(2) 0.22191(13) 0.0220(7) Uani 1 1 d . . .
O2' O 0.3582(3) 0.01878(19) 0.17391(10) 0.0300(6) Uani 1 1 d . . .
C3' C 0.4539(4) 0.1279(2) 0.24628(13) 0.0241(7) Uani 1 1 d . . .
H3'A H 0.3764 0.1842 0.2396 0.029 Uiso 1 1 calc R . .
C4' C 0.4527(4) 0.1057(2) 0.30760(13) 0.0191(6) Uani 1 1 d . . .
H4'A H 0.4722 0.1626 0.3313 0.023 Uiso 1 1 calc R . .
C5' C 0.5748(5) 0.0196(3) 0.31826(14) 0.0287(7) Uani 1 1 d . . .
H5'A H 0.5907 0.0091 0.3573 0.034 Uiso 1 1 calc R . .
H5'B H 0.6894 0.0300 0.3014 0.034 Uiso 1 1 calc R . .
C6' C 0.4781(4) -0.0674(2) 0.29166(15) 0.0268(7) Uani 1 1 d . . .
H6'A H 0.4541 -0.1182 0.3185 0.032 Uiso 1 1 calc R . .
H6'B H 0.5479 -0.0951 0.2621 0.032 Uiso 1 1 calc R . .
C7' C 0.2656(4) 0.0588(2) 0.31212(12) 0.0179(6) Uani 1 1 d . . .
C7A' C 0.1152(4) 0.1253(3) 0.29399(15) 0.0261(7) Uani 1 1 d . . .
H7AA H 0.0041 0.0940 0.3015 0.039 Uiso 1 1 calc R . .
H7AB H 0.1250 0.1378 0.2554 0.039 Uiso 1 1 calc R . .
H7AC H 0.1216 0.1862 0.3137 0.039 Uiso 1 1 calc R . .
C8' C 0.2263(4) 0.0150(2) 0.36854(13) 0.0216(6) Uani 1 1 d . . .
H8'A H 0.3295 -0.0216 0.3803 0.026 Uiso 1 1 calc R . .
H8'B H 0.1301 -0.0315 0.3646 0.026 Uiso 1 1 calc R . .
S8' S 0.16943(11) 0.09884(5) 0.42118(3) 0.02122(16) Uani 1 1 d . . .
O8A' O 0.1828(4) 0.04063(16) 0.47112(9) 0.0280(5) Uani 1 1 d . . .
O8B' O 0.2990(3) 0.17679(15) 0.41943(9) 0.0258(5) Uani 1 1 d . . .
O8C' O -0.0080(3) 0.13159(19) 0.41137(11) 0.0313(6) Uani 1 1 d . . .
Br3' Br 0.68005(5) 0.15403(3) 0.212686(14) 0.03096(11) Uani 1 1 d . . .
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'
S S 0.1246 0.1234 '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'
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
C9A C1 N2 109.1(3) . . ?
C9A C1 C12 105.9(3) . . ?
N2 C1 C12 115.0(3) . . ?
C9A C1 H1A 108.9 . . ?
N2 C1 H1A 108.9 . . ?
C12 C1 H1A 108.9 . . ?
C2 N2 C3 112.9(2) . . ?
C2 N2 C1 112.0(3) . . ?
C3 N2 C1 111.6(2) . . ?
C2 N2 H2 108(3) . . ?
C3 N2 H2 107(2) . . ?
C1 N2 H2 105(2) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C4 110.7(2) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C4A 115.5(3) . . ?
C3 C4 H4A 108.4 . . ?
C4A C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C4A C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C4B C4A C10 120.3(3) . . ?
C4B C4A C9A 97.8(2) . . ?
C10 C4A C9A 105.9(3) . . ?
C4B C4A C4 106.5(2) . . ?
C10 C4A C4 113.9(2) . . ?
C9A C4A C4 111.2(2) . . ?
C5 C4B C9 119.6(3) . . ?
C5 C4B C4A 132.9(3) . . ?
C9 C4B C4A 106.9(3) . . ?
C4B C5 C6 116.6(3) . . ?
C4B C5 H5A 121.7 . . ?
C6 C5 H5A 121.7 . . ?
C7 C6 C5 123.7(3) . . ?
C7 C6 N6 117.9(3) . . ?
C5 C6 N6 118.4(3) . . ?
O6B N6 O6A 123.0(3) . . ?
O6B N6 C6 119.2(3) . . ?
O6A N6 C6 117.8(3) . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C9 C8 C7 117.1(3) . . ?
C9 C8 H8A 121.5 . . ?
C7 C8 H8A 121.5 . . ?
C8 C9 O9 124.1(3) . . ?
C8 C9 C4B 123.6(3) . . ?
O9 C9 C4B 112.3(3) . . ?
C9 O9 C9A 104.3(2) . . ?
O9 C9A C1 115.1(3) . . ?
O9 C9A C4A 105.7(3) . . ?
C1 C9A C4A 111.2(3) . . ?
O9 C9A H9AA 108.2 . . ?
C1 C9A H9AA 108.2 . . ?
C4A C9A H9AA 108.2 . . ?
C4A C10 C11 110.5(3) . . ?
C4A C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C4A C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 115.5(3) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C1 C12 C11 117.8(3) . . ?
C1 C12 H12A 107.9 . . ?
C11 C12 H12A 107.9 . . ?
C1 C12 H12B 107.8 . . ?
C11 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C1A' C1' C2' 114.8(3) . . ?
C1A' C1' C7' 119.0(3) . . ?
C2' C1' C7' 100.4(2) . . ?
C1A' C1' C6' 116.2(3) . . ?
C2' C1' C6' 102.0(3) . . ?
C7' C1' C6' 101.7(2) . . ?
C1' C1A' H1AA 109.5 . . ?
C1' C1A' H1AB 109.5 . . ?
H1AA C1A' H1AB 109.5 . . ?
C1' C1A' H1AC 109.5 . . ?
H1AA C1A' H1AC 109.5 . . ?
H1AB C1A' H1AC 109.5 . . ?
O2' C2' C1' 127.8(3) . . ?
O2' C2' C3' 125.7(3) . . ?
C1' C2' C3' 106.5(3) . . ?
C4' C3' C2' 102.8(3) . . ?
C4' C3' Br3' 117.3(2) . . ?
C2' C3' Br3' 111.4(2) . . ?
C4' C3' H3'A 108.4 . . ?
C2' C3' H3'A 108.4 . . ?
Br3' C3' H3'A 108.4 . . ?
C3' C4' C5' 108.5(3) . . ?
C3' C4' C7' 99.0(2) . . ?
C5' C4' C7' 102.9(2) . . ?
C3' C4' H4'A 114.9 . . ?
C5' C4' H4'A 114.9 . . ?
C7' C4' H4'A 114.9 . . ?
C4' C5' C6' 103.6(3) . . ?
C4' C5' H5'A 111.0 . . ?
C6' C5' H5'A 111.0 . . ?
C4' C5' H5'B 111.0 . . ?
C6' C5' H5'B 111.0 . . ?
H5'A C5' H5'B 109.0 . . ?
C5' C6' C1' 104.6(2) . . ?
C5' C6' H6'A 110.8 . . ?
C1' C6' H6'A 110.8 . . ?
C5' C6' H6'B 110.8 . . ?
C1' C6' H6'B 110.8 . . ?
H6'A C6' H6'B 108.9 . . ?
C8' C7' C7A' 110.5(3) . . ?
C8' C7' C1' 111.0(2) . . ?
C7A' C7' C1' 111.8(3) . . ?
C8' C7' C4' 113.6(3) . . ?
C7A' C7' C4' 114.5(3) . . ?
C1' C7' C4' 94.6(2) . . ?
C7' C7A' H7AA 109.5 . . ?
C7' C7A' H7AB 109.5 . . ?
H7AA C7A' H7AB 109.5 . . ?
C7' C7A' H7AC 109.5 . . ?
H7AA C7A' H7AC 109.5 . . ?
H7AB C7A' H7AC 109.5 . . ?
C7' C8' S8' 116.5(2) . . ?
C7' C8' H8'A 108.2 . . ?
S8' C8' H8'A 108.1 . . ?
C7' C8' H8'B 108.2 . . ?
S8' C8' H8'B 108.2 . . ?
H8'A C8' H8'B 107.3 . . ?
O8C' S8' O8B' 113.58(15) . . ?
O8C' S8' O8A' 111.95(16) . . ?
O8B' S8' O8A' 112.20(14) . . ?
O8C' S8' C8' 107.89(16) . . ?
O8B' S8' C8' 106.77(14) . . ?
O8A' S8' C8' 103.72(14) . . ?
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 C9A 1.520(5) . ?
C1 N2 1.527(4) . ?
C1 C12 1.558(5) . ?
C1 H1A 1.0000 . ?
N2 C2 1.498(4) . ?
N2 C3 1.504(4) . ?
N2 H2 0.95(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.532(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C4A 1.581(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4A C4B 1.529(4) . ?
C4A C10 1.541(5) . ?
C4A C9A 1.552(4) . ?
C4B C5 1.392(5) . ?
C4B C9 1.420(4) . ?
C5 C6 1.416(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.400(5) . ?
C6 N6 1.475(4) . ?
N6 O6B 1.242(4) . ?
N6 O6A 1.253(4) . ?
C7 C8 1.411(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.390(5) . ?
C8 H8A 0.9500 . ?
C9 O9 1.393(4) . ?
O9 C9A 1.471(4) . ?
C9A H9AA 1.0000 . ?
C10 C11 1.564(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.563(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C1' C1A' 1.523(5) . ?
C1' C2' 1.536(5) . ?
C1' C7' 1.586(4) . ?
C1' C6' 1.583(5) . ?
C1A' H1AA 0.9800 . ?
C1A' H1AB 0.9800 . ?
C1A' H1AC 0.9800 . ?
C2' O2' 1.226(4) . ?
C2' C3' 1.545(5) . ?
C3' C4' 1.558(5) . ?
C3' Br3' 1.970(3) . ?
C3' H3'A 1.0000 . ?
C4' C5' 1.547(5) . ?
C4' C7' 1.589(4) . ?
C4' H4'A 1.0000 . ?
C5' C6' 1.569(5) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C7' C8' 1.561(4) . ?
C7' C7A' 1.552(4) . ?
C7A' H7AA 0.9800 . ?
C7A' H7AB 0.9800 . ?
C7A' H7AC 0.9800 . ?
C8' S8' 1.809(3) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
S8' O8C' 1.464(3) . ?
S8' O8B' 1.476(2) . ?
S8' O8A' 1.488(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 N2 C2 167.6(3) . . . . ?
C12 C1 N2 C2 -73.6(3) . . . . ?
C9A C1 N2 C3 -64.7(3) . . . . ?
C12 C1 N2 C3 54.0(4) . . . . ?
C2 N2 C3 C4 -176.2(3) . . . . ?
C1 N2 C3 C4 56.6(3) . . . . ?
N2 C3 C4 C4A -46.4(4) . . . . ?
C3 C4 C4A C4B 148.7(3) . . . . ?
C3 C4 C4A C10 -76.2(3) . . . . ?
C3 C4 C4A C9A 43.3(4) . . . . ?
C10 C4A C4B C5 -48.0(5) . . . . ?
C9A C4A C4B C5 -161.6(3) . . . . ?
C4 C4A C4B C5 83.5(4) . . . . ?
C10 C4A C4B C9 140.3(3) . . . . ?
C9A C4A C4B C9 26.7(3) . . . . ?
C4 C4A C4B C9 -88.2(3) . . . . ?
C9 C4B C5 C6 -0.4(4) . . . . ?
C4A C4B C5 C6 -171.2(3) . . . . ?
C4B C5 C6 C7 2.6(5) . . . . ?
C4B C5 C6 N6 -176.4(3) . . . . ?
C7 C6 N6 O6B 10.1(4) . . . . ?
C5 C6 N6 O6B -170.8(3) . . . . ?
C7 C6 N6 O6A -168.5(3) . . . . ?
C5 C6 N6 O6A 10.6(4) . . . . ?
C5 C6 C7 C8 -2.4(5) . . . . ?
N6 C6 C7 C8 176.6(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 O9 -177.5(3) . . . . ?
C7 C8 C9 C4B 2.4(5) . . . . ?
C5 C4B C9 C8 -2.2(5) . . . . ?
C4A C4B C9 C8 170.8(3) . . . . ?
C5 C4B C9 O9 177.7(3) . . . . ?
C4A C4B C9 O9 -9.3(4) . . . . ?
C8 C9 O9 C9A 165.7(3) . . . . ?
C4B C9 O9 C9A -14.1(3) . . . . ?
C9 O9 C9A C1 154.9(3) . . . . ?
C9 O9 C9A C4A 31.7(3) . . . . ?
N2 C1 C9A O9 -59.6(3) . . . . ?
C12 C1 C9A O9 176.1(3) . . . . ?
N2 C1 C9A C4A 60.6(4) . . . . ?
C12 C1 C9A C4A -63.7(3) . . . . ?
C4B C4A C9A O9 -35.3(3) . . . . ?
C10 C4A C9A O9 -160.0(2) . . . . ?
C4 C4A C9A O9 75.9(3) . . . . ?
C4B C4A C9A C1 -160.9(3) . . . . ?
C10 C4A C9A C1 74.4(3) . . . . ?
C4 C4A C9A C1 -49.8(4) . . . . ?
C4B C4A C10 C11 -167.7(3) . . . . ?
C9A C4A C10 C11 -58.5(3) . . . . ?
C4 C4A C10 C11 64.0(3) . . . . ?
C4A C10 C11 C12 41.1(4) . . . . ?
C9A C1 C12 C11 43.1(4) . . . . ?
N2 C1 C12 C11 -77.4(4) . . . . ?
C10 C11 C12 C1 -34.2(4) . . . . ?
C1A' C1' C2' O2' -22.9(5) . . . . ?
C7' C1' C2' O2' -151.9(3) . . . . ?
C6' C1' C2' O2' 103.7(4) . . . . ?
C1A' C1' C2' C3' 158.6(3) . . . . ?
C7' C1' C2' C3' 29.6(3) . . . . ?
C6' C1' C2' C3' -74.8(3) . . . . ?
O2' C2' C3' C4' -171.6(3) . . . . ?
C1' C2' C3' C4' 6.9(3) . . . . ?
O2' C2' C3' Br3' -45.3(4) . . . . ?
C1' C2' C3' Br3' 133.3(2) . . . . ?
C2' C3' C4' C5' 66.4(3) . . . . ?
Br3' C3' C4' C5' -56.1(3) . . . . ?
C2' C3' C4' C7' -40.6(3) . . . . ?
Br3' C3' C4' C7' -163.1(2) . . . . ?
C3' C4' C5' C6' -68.9(3) . . . . ?
C7' C4' C5' C6' 35.4(3) . . . . ?
C4' C5' C6' C1' -1.8(3) . . . . ?
C1A' C1' C6' C5' -163.2(3) . . . . ?
C2' C1' C6' C5' 71.1(3) . . . . ?
C7' C1' C6' C5' -32.3(3) . . . . ?
C1A' C1' C7' C8' 63.3(4) . . . . ?
C2' C1' C7' C8' -170.5(3) . . . . ?
C6' C1' C7' C8' -65.8(3) . . . . ?
C1A' C1' C7' C7A' -60.6(4) . . . . ?
C2' C1' C7' C7A' 65.6(3) . . . . ?
C6' C1' C7' C7A' 170.3(3) . . . . ?
C1A' C1' C7' C4' -179.2(3) . . . . ?
C2' C1' C7' C4' -53.0(3) . . . . ?
C6' C1' C7' C4' 51.7(3) . . . . ?
C3' C4' C7' C8' 172.9(3) . . . . ?
C5' C4' C7' C8' 61.3(3) . . . . ?
C3' C4' C7' C7A' -58.9(3) . . . . ?
C5' C4' C7' C7A' -170.5(3) . . . . ?
C3' C4' C7' C1' 57.5(3) . . . . ?
C5' C4' C7' C1' -54.0(3) . . . . ?
C7A' C7' C8' S8' -52.3(3) . . . . ?
C1' C7' C8' S8' -177.0(2) . . . . ?
C4' C7' C8' S8' 77.9(3) . . . . ?
C7' C8' S8' O8C' 74.5(3) . . . . ?
C7' C8' S8' O8B' -47.9(3) . . . . ?
C7' C8' S8' O8A' -166.6(2) . . . . ?
