#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:57:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178413 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023444.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_4023444
loop_
_publ_author_name
'Paul B. Hurley'
'Gregory R. Dake'
_publ_section_title
;
 Synthetic Studies toward Halichlorine: Complex Azaspirocycle Formation
 with Use of an NBS-Promoted Semipinacol Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4131
_journal_page_last               4138
_journal_paper_doi               10.1021/jo800336k
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C31 H42 Br N O5 S'
_chemical_formula_weight         620.63
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 111.993(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8742(16)
_cell_length_b                   7.6796(9)
_cell_length_c                   15.1970(15)
_cell_measurement_reflns_used    8974
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      2.72
_cell_volume                     1501.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33368
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.027(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         7137
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0323P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                5915
_reflns_number_total             7137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800336k-File001.cif
_cod_data_source_block           gd016
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023444
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.19539(15) 0.3858(3) 0.50540(15) 0.0254(5) Uani 1 1 d . . .
H1 H 0.1888 0.4688 0.5535 0.031 Uiso 1 1 calc R . .
C2 C 0.09354(15) 0.2853(3) 0.46798(15) 0.0306(5) Uani 1 1 d . . .
H2A H 0.0661 0.2681 0.5189 0.037 Uiso 1 1 calc R . .
H2B H 0.1038 0.1698 0.4439 0.037 Uiso 1 1 calc R . .
C3 C 0.01844(15) 0.3955(3) 0.38773(15) 0.0284(5) Uani 1 1 d . . .
H3A H -0.0360 0.4462 0.4074 0.034 Uiso 1 1 calc R . .
H3B H -0.0157 0.3227 0.3307 0.034 Uiso 1 1 calc R . .
C4 C 0.08299(15) 0.5430(3) 0.36540(15) 0.0223(4) Uani 1 1 d . . .
H4 H 0.0685 0.6487 0.3968 0.027 Uiso 1 1 calc R . .
C5 C 0.20078(15) 0.5016(3) 0.42278(14) 0.0213(4) Uani 1 1 d . . .
C7 C 0.36892(15) 0.4635(3) 0.38219(14) 0.0227(4) Uani 1 1 d . . .
H7 H 0.4000 0.3562 0.3665 0.027 Uiso 1 1 calc R . .
C8 C 0.43011(16) 0.5002(3) 0.48601(15) 0.0267(5) Uani 1 1 d . . .
H8A H 0.5005 0.5407 0.4936 0.032 Uiso 1 1 calc R . .
H8B H 0.4379 0.3906 0.5223 0.032 Uiso 1 1 calc R . .
C9 C 0.37901(15) 0.6376(3) 0.52792(14) 0.0258(5) Uani 1 1 d . . .
H9A H 0.3823 0.5983 0.5910 0.031 Uiso 1 1 calc R . .
H9B H 0.4180 0.7483 0.5366 0.031 Uiso 1 1 calc R . .
C10 C 0.26584(15) 0.6689(3) 0.46376(14) 0.0228(4) Uani 1 1 d . . .
H10 H 0.2658 0.7402 0.4087 0.027 Uiso 1 1 calc R . .
C12 C 0.04528(15) 0.5919(3) 0.25901(15) 0.0245(5) Uani 1 1 d . . .
H12 H 0.0633 0.4953 0.2237 0.029 Uiso 1 1 calc R . .
C13 C 0.09711(16) 0.7600(3) 0.24484(15) 0.0282(5) Uani 1 1 d . . .
H13A H 0.0820 0.8525 0.2832 0.034 Uiso 1 1 calc R . .
H13B H 0.1733 0.7414 0.2710 0.034 Uiso 1 1 calc R . .
C14 C 0.06667(16) 0.8273(3) 0.14451(14) 0.0295(4) Uani 1 1 d . . .
H14A H -0.0100 0.8272 0.1124 0.035 Uiso 1 1 calc R . .
H14B H 0.0916 0.9484 0.1457 0.035 Uiso 1 1 calc R . .
C15 C -0.07340(17) 0.6161(3) 0.21937(18) 0.0403(6) Uani 1 1 d . . .
H15A H -0.0918 0.7090 0.2544 0.061 Uiso 1 1 calc R . .
H15B H -0.1067 0.5072 0.2263 0.061 Uiso 1 1 calc R . .
H15C H -0.0974 0.6474 0.1520 0.061 Uiso 1 1 calc R . .
C17 C 0.09283(18) 0.7873(4) 0.00197(14) 0.0371(6) Uani 1 1 d . . .
H17A H 0.1024 0.9152 0.0061 0.045 Uiso 1 1 calc R . .
H17B H 0.0202 0.7626 -0.0405 0.045 Uiso 1 1 calc R . .
C18 C 0.16568(17) 0.7081(3) -0.03826(15) 0.0301(5) Uani 1 1 d . . .
C19 C 0.13092(17) 0.6519(3) -0.13189(16) 0.0321(5) Uani 1 1 d . . .
H19 H 0.0589 0.6587 -0.1699 0.039 Uiso 1 1 calc R . .
C19' C 0.27198(18) 0.6944(3) 0.01583(16) 0.0339(5) Uani 1 1 d . . .
H19' H 0.2979 0.7320 0.0800 0.041 Uiso 1 1 calc R . .
C20 C 0.19849(17) 0.5862(3) -0.17115(16) 0.0332(5) Uani 1 1 d . . .
H20 H 0.1730 0.5506 -0.2357 0.040 Uiso 1 1 calc R . .
C20' C 0.33975(19) 0.6274(3) -0.02217(16) 0.0356(6) Uani 1 1 d . . .
H20' H 0.4116 0.6187 0.0160 0.043 Uiso 1 1 calc R . .
C21 C 0.30378(18) 0.5723(3) -0.11597(16) 0.0313(5) Uani 1 1 d . . .
C23 C 0.3404(2) 0.4394(4) -0.24166(18) 0.0528(8) Uani 1 1 d . . .
H23A H 0.2854 0.3534 -0.2501 0.079 Uiso 1 1 calc R . .
H23B H 0.3980 0.3842 -0.2536 0.079 Uiso 1 1 calc R . .
H23C H 0.3127 0.5357 -0.2863 0.079 Uiso 1 1 calc R . .
C26 C 0.27038(15) 0.2079(3) 0.22587(14) 0.0246(5) Uani 1 1 d . . .
C27' C 0.21629(14) 0.2990(3) 0.14284(13) 0.0260(4) Uani 1 1 d . . .
H27' H 0.1622 0.3774 0.1399 0.031 Uiso 1 1 calc R . .
C27 C 0.34969(16) 0.0942(3) 0.23044(16) 0.0292(5) Uani 1 1 d . . .
H27 H 0.3864 0.0327 0.2874 0.035 Uiso 1 1 calc R . .
C28' C 0.24290(17) 0.2733(3) 0.06478(15) 0.0308(6) Uani 1 1 d . . .
H28' H 0.2066 0.3360 0.0081 0.037 Uiso 1 1 calc R . .
C28 C 0.37501(18) 0.0711(3) 0.15144(17) 0.0360(6) Uani 1 1 d . . .
H28 H 0.4300 -0.0057 0.1548 0.043 Uiso 1 1 calc R . .
C29 C 0.32096(18) 0.1588(3) 0.06676(17) 0.0334(5) Uani 1 1 d . . .
C30 C 0.3502(2) 0.1325(4) -0.01854(18) 0.0477(7) Uani 1 1 d . . .
H30A H 0.4067 0.0472 -0.0032 0.072 Uiso 0.50 1 calc PR . .
H30B H 0.3732 0.2435 -0.0358 0.072 Uiso 0.50 1 calc PR . .
H30C H 0.2897 0.0898 -0.0719 0.072 Uiso 0.50 1 calc PR . .
H30D H 0.3064 0.2064 -0.0708 0.072 Uiso 0.50 1 calc PR . .
H30E H 0.3399 0.0102 -0.0382 0.072 Uiso 0.50 1 calc PR . .
H30F H 0.4234 0.1639 -0.0021 0.072 Uiso 0.50 1 calc PR . .
C31 C 0.37788(16) 0.6072(3) 0.31427(15) 0.0274(5) Uani 1 1 d . . .
H31A H 0.3230 0.5902 0.2507 0.033 Uiso 1 1 calc R . .
H31B H 0.3671 0.7226 0.3382 0.033 Uiso 1 1 calc R . .
C32 C 0.48227(17) 0.6028(3) 0.30649(17) 0.0356(6) Uani 1 1 d . . .
H32 H 0.5376 0.6632 0.3534 0.043 Uiso 1 1 calc R . .
C33 C 0.5029(2) 0.5225(4) 0.2403(2) 0.0504(7) Uani 1 1 d . . .
H33A H 0.4495 0.4608 0.1922 0.061 Uiso 1 1 calc R . .
H33B H 0.5712 0.5257 0.2401 0.061 Uiso 1 1 calc R . .
N6 N 0.25669(13) 0.4202(2) 0.36299(12) 0.0209(4) Uani 1 1 d . . .
O11 O 0.28443(12) 0.2827(2) 0.55458(11) 0.0293(4) Uani 1 1 d . . .
O16 O 0.11148(12) 0.7187(2) 0.09385(10) 0.0332(4) Uani 1 1 d . . .
O22 O 0.37686(12) 0.5045(2) -0.14688(11) 0.0422(4) Uani 1 1 d . . .
O25 O 0.29087(11) 0.09337(19) 0.39178(10) 0.0288(3) Uani 1 1 d . . .
O25' O 0.11905(11) 0.19872(19) 0.28752(10) 0.0288(3) Uani 1 1 d . . .
S24 S 0.22964(4) 0.21954(7) 0.32310(4) 0.02240(12) Uani 1 1 d . . .
Br01 Br 0.206037(16) 0.81401(3) 0.537775(14) 0.03183(6) Uani 1 1 d . . .
H11 H 0.283(2) 0.197(4) 0.5259(18) 0.038(8) Uiso 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
O11 C1 C2 114.64(18) . . ?
O11 C1 C5 116.47(16) . . ?
C2 C1 C5 107.79(16) . . ?
O11 C1 H1 105.7 . . ?
C2 C1 H1 105.7 . . ?
C5 C1 H1 105.7 . . ?
C1 C2 C3 106.12(18) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C2 C3 C4 107.49(16) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C12 C4 C3 114.02(17) . . ?
C12 C4 C5 120.25(17) . . ?
C3 C4 C5 107.21(16) . . ?
C12 C4 H4 104.6 . . ?
C3 C4 H4 104.6 . . ?
C5 C4 H4 104.6 . . ?
N6 C5 C10 103.13(15) . . ?
N6 C5 C1 115.55(17) . . ?
C10 C5 C1 110.03(16) . . ?
N6 C5 C4 113.96(16) . . ?
C10 C5 C4 112.45(17) . . ?
C1 C5 C4 102.02(15) . . ?
N6 C7 C8 112.21(17) . . ?
N6 C7 C31 111.26(16) . . ?
C8 C7 C31 114.15(17) . . ?
N6 C7 H7 106.2 . . ?
C8 C7 H7 106.2 . . ?
C31 C7 H7 106.2 . . ?
C7 C8 C9 113.25(17) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 111.56(16) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C5 115.41(16) . . ?
C9 C10 Br01 106.05(13) . . ?
C5 C10 Br01 112.88(13) . . ?
C9 C10 H10 107.4 . . ?
C5 C10 H10 107.4 . . ?
Br01 C10 H10 107.4 . . ?
C13 C12 C15 109.46(18) . . ?
C13 C12 C4 111.01(17) . . ?
C15 C12 C4 109.39(18) . . ?
C13 C12 H12 109.0 . . ?
C15 C12 H12 109.0 . . ?
C4 C12 H12 109.0 . . ?
C14 C13 C12 117.46(19) . . ?
C14 C13 H13A 107.9 . . ?
C12 C13 H13A 107.9 . . ?
C14 C13 H13B 107.9 . . ?
C12 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
O16 C14 C13 109.32(18) . . ?
O16 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O16 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O16 C17 C18 110.42(18) . . ?
O16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C19' 117.6(2) . . ?
C19 C18 C17 121.2(2) . . ?
C19' C18 C17 121.1(2) . . ?
C20 C19 C18 121.6(2) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C20' C19' C18 121.2(2) . . ?
C20' C19' H19' 119.4 . . ?
C18 C19' H19' 119.4 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C19' C20' C21 120.4(2) . . ?
C19' C20' H20' 119.8 . . ?
C21 C20' H20' 119.8 . . ?
O22 C21 C20' 116.1(2) . . ?
O22 C21 C20 124.6(2) . . ?
C20' C21 C20 119.3(2) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 C26 C27' 120.72(19) . . ?
C27 C26 S24 119.05(17) . . ?
C27' C26 S24 119.92(15) . . ?
C28' C27' C26 118.7(2) . . ?
C28' C27' H27' 120.7 . . ?
C26 C27' H27' 120.7 . . ?
C28 C27 C26 119.5(2) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27' C28' C29 122.0(2) . . ?
C27' C28' H28' 119.0 . . ?
C29 C28' H28' 119.0 . . ?
C27 C28 C29 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C28' C29 C28 118.1(2) . . ?
C28' C29 C30 121.7(2) . . ?
C28 C29 C30 120.2(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C30 H30D 109.5 . . ?
H30A C30 H30D 141.1 . . ?
H30B C30 H30D 56.3 . . ?
H30C C30 H30D 56.3 . . ?
C29 C30 H30E 109.5 . . ?
H30A C30 H30E 56.3 . . ?
H30B C30 H30E 141.1 . . ?
H30C C30 H30E 56.3 . . ?
H30D C30 H30E 109.5 . . ?
C29 C30 H30F 109.5 . . ?
H30A C30 H30F 56.3 . . ?
H30B C30 H30F 56.3 . . ?
H30C C30 H30F 141.1 . . ?
H30D C30 H30F 109.5 . . ?
H30E C30 H30F 109.5 . . ?
C32 C31 C7 110.99(19) . . ?
C32 C31 H31A 109.4 . . ?
C7 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C7 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C33 C32 C31 124.9(2) . . ?
C33 C32 H32 117.6 . . ?
C31 C32 H32 117.6 . . ?
C32 C33 H33A 120.0 . . ?
C32 C33 H33B 120.0 . . ?
H33A C33 H33B 120.0 . . ?
C7 N6 C5 120.68(16) . . ?
C7 N6 S24 110.69(13) . . ?
C5 N6 S24 120.26(13) . . ?
C1 O11 H11 110.0(19) . . ?
C17 O16 C14 110.95(16) . . ?
C21 O22 C23 116.81(19) . . ?
O25' S24 O25 117.07(9) . . ?
O25' S24 N6 107.92(9) . . ?
O25 S24 N6 111.74(9) . . ?
O25' S24 C26 108.12(9) . . ?
O25 S24 C26 106.49(10) . . ?
N6 S24 C26 104.74(9) . . ?
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 O11 1.421(2) . ?
C1 C2 1.521(3) . ?
C1 C5 1.563(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.529(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.558(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C12 1.548(3) . ?
C4 C5 1.570(3) . ?
C4 H4 1.0000 . ?
C5 N6 1.532(3) . ?
C5 C10 1.559(3) . ?
C7 N6 1.510(2) . ?
C7 C8 1.512(3) . ?
C7 C31 1.548(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.536(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.526(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 Br01 1.974(2) . ?
C10 H10 1.0000 . ?
C12 C13 1.532(3) . ?
C12 C15 1.538(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.513(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O16 1.426(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 O16 1.423(2) . ?
C17 C18 1.493(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.389(3) . ?
C18 C19' 1.398(3) . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C19' C20' 1.374(3) . ?
C19' H19' 0.9500 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9500 . ?
C20' C21 1.388(3) . ?
C20' H20' 0.9500 . ?
C21 O22 1.370(3) . ?
C23 O22 1.426(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C26 C27 1.386(3) . ?
C26 C27' 1.391(3) . ?
C26 S24 1.771(2) . ?
C27' C28' 1.382(3) . ?
C27' H27' 0.9500 . ?
C27 C28 1.383(3) . ?
C27 H27 0.9500 . ?
C28' C29 1.387(3) . ?
C28' H28' 0.9500 . ?
C28 C29 1.396(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.510(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30 H30D 0.9800 . ?
C30 H30E 0.9800 . ?
C30 H30F 0.9800 . ?
C31 C32 1.497(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.299(3) . ?
C32 H32 0.9500 . ?
C33 H33A 0.9500 . ?
C33 H33B 0.9500 . ?
N6 S24 1.6473(18) . ?
O11 H11 0.78(3) . ?
O25 S24 1.4442(15) . ?
O25' S24 1.4320(14) . ?
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
O11 C1 C2 C3 -158.16(18) . . . . ?
C5 C1 C2 C3 -26.7(2) . . . . ?
C1 C2 C3 C4 10.8(2) . . . . ?
C2 C3 C4 C12 144.38(18) . . . . ?
C2 C3 C4 C5 8.7(2) . . . . ?
O11 C1 C5 N6 37.4(3) . . . . ?
C2 C1 C5 N6 -93.0(2) . . . . ?
O11 C1 C5 C10 -78.8(2) . . . . ?
C2 C1 C5 C10 150.73(17) . . . . ?
O11 C1 C5 C4 161.63(18) . . . . ?
C2 C1 C5 C4 31.2(2) . . . . ?
C12 C4 C5 N6 -31.0(3) . . . . ?
C3 C4 C5 N6 101.40(19) . . . . ?
C12 C4 C5 C10 86.0(2) . . . . ?
C3 C4 C5 C10 -141.69(18) . . . . ?
C12 C4 C5 C1 -156.21(18) . . . . ?
C3 C4 C5 C1 -23.9(2) . . . . ?
N6 C7 C8 C9 -52.3(2) . . . . ?
C31 C7 C8 C9 75.5(2) . . . . ?
C7 C8 C9 C10 15.4(2) . . . . ?
C8 C9 C10 C5 44.3(2) . . . . ?
C8 C9 C10 Br01 170.09(14) . . . . ?
N6 C5 C10 C9 -62.1(2) . . . . ?
C1 C5 C10 C9 61.7(2) . . . . ?
C4 C5 C10 C9 174.67(17) . . . . ?
N6 C5 C10 Br01 175.69(12) . . . . ?
C1 C5 C10 Br01 -60.50(19) . . . . ?
C4 C5 C10 Br01 52.5(2) . . . . ?
C3 C4 C12 C13 168.56(17) . . . . ?
C5 C4 C12 C13 -62.0(2) . . . . ?
C3 C4 C12 C15 47.7(2) . . . . ?
C5 C4 C12 C15 177.05(19) . . . . ?
C15 C12 C13 C14 -58.0(3) . . . . ?
C4 C12 C13 C14 -178.84(18) . . . . ?
C12 C13 C14 O16 -72.8(2) . . . . ?
O16 C17 C18 C19 135.9(2) . . . . ?
O16 C17 C18 C19' -46.8(3) . . . . ?
C19' C18 C19 C20 -0.7(3) . . . . ?
C17 C18 C19 C20 176.8(2) . . . . ?
C19 C18 C19' C20' -0.1(3) . . . . ?
C17 C18 C19' C20' -177.6(2) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C18 C19' C20' C21 0.3(4) . . . . ?
C19' C20' C21 O22 -178.8(2) . . . . ?
C19' C20' C21 C20 0.2(4) . . . . ?
C19 C20 C21 O22 178.0(2) . . . . ?
C19 C20 C21 C20' -0.9(4) . . . . ?
C27 C26 C27' C28' 0.3(3) . . . . ?
S24 C26 C27' C28' -173.30(17) . . . . ?
C27' C26 C27 C28 -0.2(3) . . . . ?
S24 C26 C27 C28 173.51(18) . . . . ?
C26 C27' C28' C29 0.5(3) . . . . ?
C26 C27 C28 C29 -0.8(4) . . . . ?
C27' C28' C29 C28 -1.5(3) . . . . ?
C27' C28' C29 C30 -179.5(2) . . . . ?
C27 C28 C29 C28' 1.6(4) . . . . ?
C27 C28 C29 C30 179.6(2) . . . . ?
N6 C7 C31 C32 -158.24(18) . . . . ?
C8 C7 C31 C32 73.5(2) . . . . ?
C7 C31 C32 C33 95.2(3) . . . . ?
C8 C7 N6 C5 31.8(3) . . . . ?
C31 C7 N6 C5 -97.5(2) . . . . ?
C8 C7 N6 S24 -116.49(16) . . . . ?
C31 C7 N6 S24 114.24(16) . . . . ?
C10 C5 N6 C7 22.2(2) . . . . ?
C1 C5 N6 C7 -97.8(2) . . . . ?
C4 C5 N6 C7 144.44(18) . . . . ?
C10 C5 N6 S24 167.52(13) . . . . ?
C1 C5 N6 S24 47.4(2) . . . . ?
C4 C5 N6 S24 -70.3(2) . . . . ?
C18 C17 O16 C14 162.30(19) . . . . ?
C13 C14 O16 C17 -174.45(19) . . . . ?
C20' C21 O22 C23 177.0(2) . . . . ?
C20 C21 O22 C23 -2.0(4) . . . . ?
C7 N6 S24 O25' -167.92(13) . . . . ?
C5 N6 S24 O25' 43.66(17) . . . . ?
C7 N6 S24 O25 62.00(15) . . . . ?
C5 N6 S24 O25 -86.42(16) . . . . ?
C7 N6 S24 C26 -52.89(15) . . . . ?
C5 N6 S24 C26 158.69(15) . . . . ?
C27 C26 S24 O25' -128.40(17) . . . . ?
C27' C26 S24 O25' 45.3(2) . . . . ?
C27 C26 S24 O25 -1.80(19) . . . . ?
C27' C26 S24 O25 171.94(17) . . . . ?
C27 C26 S24 N6 116.71(17) . . . . ?
C27' C26 S24 N6 -69.55(19) . . . . ?
