# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
#TrackingRef '- C2CC30341H_ccdc_816966_cif.txt'

_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Min Shi'
_publ_contact_author_email       mshi@mail.sioc.ac.cn
loop_
_publ_author_name
'Min Shi'
'Di-Han Zhang'

data_cd21195
_database_code_depnum_ccdc_archive 'CCDC 816966'
#TrackingRef 'cd21195.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br N O3 S'
_chemical_formula_weight         408.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.4860(17)
_cell_length_b                   7.4766(11)
_cell_length_c                   20.639(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.970(3)
_cell_angle_gamma                90.00
_cell_volume                     1762.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3031
_cell_measurement_theta_min      5.787
_cell_measurement_theta_max      51.083

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.089
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    2.466
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.53589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9137
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3455
_reflns_number_gt                2241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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.
;

_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^)+(0.0213P)^2^+3.0452P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3455
_refine_ls_number_parameters     300
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002

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 0.9569(3) 0.7676(6) 0.44278(14) 0.0878(8) Uani 0.654(10) 1 d P A 1
Br1' Br 0.9077(9) 0.7233(8) 0.4451(2) 0.0902(16) Uani 0.346(10) 1 d P A 2
S1 S 0.91020(11) 0.88921(19) -0.10071(6) 0.0635(4) Uani 1 1 d . . .
O1 O 0.8923(4) 1.0789(5) -0.09662(17) 0.0877(12) Uani 1 1 d . . .
O2 O 1.0163(3) 0.8163(6) -0.07023(16) 0.0854(12) Uani 1 1 d . . .
O3 O 0.8000(3) 0.6117(5) -0.07474(16) 0.0791(11) Uani 1 1 d . . .
N1 N 0.7890(3) 0.8028(6) -0.07334(17) 0.0626(11) Uani 1 1 d . A .
C1 C 0.7771(5) 0.8532(7) -0.0048(2) 0.0688(14) Uani 1 1 d . . .
H1A H 0.7055 0.9201 -0.0020 0.083 Uiso 0.654(10) 1 calc PR A 1
H1B H 0.8429 0.9262 0.0126 0.083 Uiso 0.654(10) 1 calc PR A 1
H1C H 0.6965 0.8534 0.0037 0.083 Uiso 0.346(10) 1 d PR A 2
H1D H 0.8133 0.9667 0.0058 0.083 Uiso 0.346(10) 1 d PR A 2
C2 C 0.7744(10) 0.6717(15) 0.0341(4) 0.064(3) Uani 0.654(10) 1 d P A 1
H2 H 0.6936 0.6297 0.0340 0.077 Uiso 0.654(10) 1 calc PR A 1
C3 C 0.8438(18) 0.544(3) -0.0070(10) 0.085(6) Uani 0.654(10) 1 d P A 1
H3A H 0.9277 0.5596 0.0024 0.101 Uiso 0.654(10) 1 calc PR A 1
H3B H 0.8234 0.4199 -0.0010 0.101 Uiso 0.654(10) 1 calc PR A 1
C2' C 0.843(2) 0.704(2) 0.0311(8) 0.062(5) Uani 0.346(10) 1 d P A 2
H2' H 0.9263 0.7277 0.0282 0.074 Uiso 0.346(10) 1 calc PR A 2
C3' C 0.812(3) 0.574(4) -0.0144(17) 0.062(8) Uani 0.346(10) 1 d P A 2
H3'1 H 0.8698 0.4797 -0.0080 0.074 Uiso 0.346(10) 1 calc PR A 2
H3'2 H 0.7382 0.5239 -0.0040 0.074 Uiso 0.346(10) 1 calc PR A 2
C4 C 0.8288(5) 0.6931(7) 0.1018(2) 0.0683(14) Uani 1 1 d . . .
H4 H 0.9047 0.7377 0.1070 0.082 Uiso 0.654(10) 1 calc PR A 1
H4' H 0.7567 0.6857 0.1211 0.082 Uiso 0.346(10) 1 d PR A 2
C5 C 0.7827(6) 0.6568(10) 0.1539(3) 0.061(2) Uani 0.654(10) 1 d P A 1
H5 H 0.7086 0.6056 0.1471 0.073 Uiso 0.654(10) 1 calc PR A 1
C6 C 0.8268(17) 0.682(2) 0.2237(9) 0.053(4) Uani 0.654(10) 1 d P A 1
C7 C 0.9381(13) 0.7530(17) 0.2407(6) 0.054(3) Uani 0.654(10) 1 d P A 1
H7 H 0.9869 0.7816 0.2090 0.064 Uiso 0.654(10) 1 calc PR A 1
C8 C 0.975(2) 0.780(4) 0.3077(14) 0.069(6) Uani 0.654(10) 1 d P A 1
H8 H 1.0460 0.8358 0.3204 0.083 Uiso 0.654(10) 1 calc PR A 1
C10 C 0.797(2) 0.661(4) 0.3386(9) 0.065(5) Uani 0.654(10) 1 d P A 1
H10 H 0.7486 0.6346 0.3708 0.079 Uiso 0.654(10) 1 calc PR A 1
C11 C 0.7604(15) 0.634(2) 0.2725(9) 0.057(3) Uani 0.654(10) 1 d P A 1
H11 H 0.6877 0.5817 0.2611 0.068 Uiso 0.654(10) 1 calc PR A 1
C5' C 0.9017(12) 0.7084(19) 0.1491(6) 0.059(5) Uani 0.346(10) 1 d P A 2
H5' H 0.9779 0.7248 0.1388 0.071 Uiso 0.346(10) 1 calc PR A 2
C6' C 0.890(3) 0.705(3) 0.2205(11) 0.040(5) Uani 0.346(10) 1 d P A 2
C7' C 0.992(2) 0.768(3) 0.2581(13) 0.053(5) Uani 0.346(10) 1 d P A 2
H7' H 1.0548 0.8083 0.2367 0.064 Uiso 0.346(10) 1 calc PR A 2
C8' C 1.002(4) 0.770(7) 0.321(2) 0.051(7) Uani 0.346(10) 1 d PU A 2
H8' H 1.0720 0.8016 0.3446 0.062 Uiso 0.346(10) 1 calc PR A 2
C10' C 0.805(4) 0.656(6) 0.3192(14) 0.041(6) Uani 0.346(10) 1 d PU A 2
H10' H 0.7435 0.6143 0.3412 0.049 Uiso 0.346(10) 1 calc PR A 2
C11' C 0.798(2) 0.649(3) 0.2507(12) 0.047(7) Uani 0.346(10) 1 d P A 2
H11' H 0.7305 0.6067 0.2267 0.057 Uiso 0.346(10) 1 calc PR A 2
C9 C 0.9058(5) 0.7255(7) 0.3531(2) 0.0588(12) Uani 1 1 d . . .
C12 C 0.8965(4) 0.8260(6) -0.1829(2) 0.0536(11) Uani 1 1 d . . .
C13 C 0.8046(4) 0.8947(6) -0.2250(2) 0.0583(12) Uani 1 1 d . . .
H13 H 0.7459 0.9619 -0.2090 0.070 Uiso 1 1 calc R . .
C14 C 0.8023(4) 0.8615(6) -0.2903(2) 0.0561(12) Uani 1 1 d . . .
H14 H 0.7401 0.9045 -0.3185 0.067 Uiso 1 1 calc R . .
C15 C 0.8900(4) 0.7659(6) -0.3154(2) 0.0532(11) Uani 1 1 d . . .
C16 C 0.9773(4) 0.6948(7) -0.2724(2) 0.0612(12) Uani 1 1 d . . .
H16 H 1.0355 0.6259 -0.2882 0.073 Uiso 1 1 calc R . .
C17 C 0.9802(4) 0.7239(7) -0.2061(2) 0.0599(12) Uani 1 1 d . . .
H17 H 1.0393 0.6735 -0.1776 0.072 Uiso 1 1 calc R . .
C18 C 0.8915(6) 0.7395(8) -0.3875(2) 0.0824(17) Uani 1 1 d . . .
H18A H 0.8127 0.7264 -0.4076 0.124 Uiso 1 1 calc R . .
H18B H 0.9355 0.6339 -0.3952 0.124 Uiso 1 1 calc R . .
H18C H 0.9272 0.8414 -0.4058 0.124 Uiso 1 1 calc R . .

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 0.0897(14) 0.1247(18) 0.0475(7) -0.0110(9) -0.0003(8) 0.0118(11)
Br1' 0.128(4) 0.103(2) 0.0416(10) 0.0011(12) 0.020(2) 0.011(2)
S1 0.0673(8) 0.0744(9) 0.0465(6) -0.0044(6) -0.0043(5) -0.0127(7)
O1 0.128(3) 0.066(3) 0.069(2) -0.0132(19) 0.005(2) -0.014(2)
O2 0.065(2) 0.127(3) 0.059(2) 0.003(2) -0.0139(17) -0.012(2)
O3 0.112(3) 0.079(3) 0.046(2) -0.0075(18) 0.0098(18) -0.026(2)
N1 0.066(2) 0.078(3) 0.042(2) -0.0033(19) -0.0013(17) 0.000(2)
C1 0.080(3) 0.082(4) 0.043(2) -0.004(2) 0.003(2) 0.010(3)
C2 0.060(6) 0.082(7) 0.048(5) 0.000(4) 0.001(5) -0.011(5)
C3 0.111(11) 0.090(11) 0.054(7) 0.033(7) 0.014(8) 0.039(8)
C2' 0.081(13) 0.055(11) 0.048(8) 0.011(8) -0.002(10) 0.003(11)
C3' 0.090(17) 0.029(11) 0.060(15) -0.007(11) -0.017(11) 0.005(12)
C4 0.069(3) 0.084(4) 0.053(3) 0.007(3) 0.009(3) -0.007(3)
C5 0.061(5) 0.064(5) 0.056(5) 0.005(4) 0.000(4) 0.002(4)
C6 0.053(9) 0.048(7) 0.060(10) 0.005(6) 0.010(10) 0.000(8)
C7 0.055(10) 0.059(7) 0.047(10) 0.003(6) 0.007(6) -0.013(8)
C8 0.057(11) 0.064(9) 0.084(14) -0.002(8) -0.002(8) -0.011(7)
C10 0.068(9) 0.084(8) 0.048(11) 0.010(9) 0.027(8) 0.008(6)
C11 0.056(9) 0.060(6) 0.057(9) 0.007(6) 0.015(5) -0.005(6)
C5' 0.062(9) 0.076(11) 0.040(7) 0.015(7) 0.008(6) -0.006(7)
C6' 0.055(18) 0.031(11) 0.034(10) -0.003(7) 0.003(13) 0.005(13)
C7' 0.056(14) 0.064(11) 0.041(12) 0.006(9) 0.008(11) -0.006(12)
C8' 0.048(15) 0.048(11) 0.060(15) -0.008(11) 0.018(12) -0.003(11)
C10' 0.045(10) 0.050(10) 0.032(15) 0.010(11) 0.024(11) 0.005(7)
C11' 0.05(2) 0.053(13) 0.04(2) 0.007(14) -0.002(13) -0.011(13)
C9 0.069(3) 0.062(3) 0.046(2) 0.000(2) 0.003(2) 0.012(3)
C12 0.054(3) 0.057(3) 0.049(2) -0.001(2) 0.003(2) -0.006(2)
C13 0.060(3) 0.057(3) 0.057(3) 0.003(2) 0.001(2) 0.011(2)
C14 0.068(3) 0.055(3) 0.043(2) 0.004(2) -0.005(2) 0.004(2)
C15 0.067(3) 0.045(3) 0.049(2) 0.001(2) 0.013(2) -0.008(2)
C16 0.064(3) 0.058(3) 0.063(3) -0.001(2) 0.012(2) 0.007(2)
C17 0.055(3) 0.063(3) 0.061(3) 0.002(2) -0.002(2) 0.003(2)
C18 0.115(5) 0.079(4) 0.053(3) 0.002(3) 0.009(3) 0.000(3)

_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 C9 1.909(5) . ?
Br1' C9 1.898(6) . ?
S1 O2 1.421(4) . ?
S1 O1 1.437(4) . ?
S1 N1 1.685(4) . ?
S1 C12 1.753(4) . ?
O3 C3' 1.27(3) . ?
O3 N1 1.435(5) . ?
O3 C3 1.521(19) . ?
N1 C1 1.483(6) . ?
C1 C2' 1.504(18) . ?
C1 C2 1.579(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C2 C4 1.478(10) . ?
C2 C3 1.55(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2' C3' 1.37(4) . ?
C2' C4 1.488(19) . ?
C2' H2' 0.9800 . ?
C3' H3'1 0.9700 . ?
C3' H3'2 0.9700 . ?
C4 C5' 1.223(13) . ?
C4 C5 1.277(8) . ?
C4 H4 0.9300 . ?
C4 H4' 0.9566 . ?
C5 C6 1.49(2) . ?
C5 H4' 0.7433 . ?
C5 H5 0.9300 . ?
C6 C11 1.374(14) . ?
C6 C7 1.39(2) . ?
C7 C8 1.42(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.35(3) . ?
C8 H8 0.9300 . ?
C10 C9 1.35(3) . ?
C10 C11 1.40(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C5' C6' 1.49(3) . ?
C5' H5' 0.9300 . ?
C6' C11' 1.35(3) . ?
C6' C7' 1.42(2) . ?
C7' C8' 1.29(5) . ?
C7' H7' 0.9300 . ?
C8' C9 1.38(5) . ?
C8' H8' 0.9300 . ?
C10' C9 1.39(5) . ?
C10' C11' 1.41(3) . ?
C10' H10' 0.9300 . ?
C11' H11' 0.9300 . ?
C12 C17 1.353(6) . ?
C12 C13 1.393(6) . ?
C13 C14 1.368(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(6) . ?
C15 C18 1.503(6) . ?
C16 C17 1.383(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
O2 S1 O1 118.3(2) . . ?
O2 S1 N1 113.9(2) . . ?
O1 S1 N1 103.3(2) . . ?
O2 S1 C12 108.1(2) . . ?
O1 S1 C12 108.9(2) . . ?
N1 S1 C12 103.1(2) . . ?
C3' O3 N1 101.6(13) . . ?
C3' O3 C3 15(2) . . ?
N1 O3 C3 109.4(9) . . ?
O3 N1 C1 106.8(4) . . ?
O3 N1 S1 107.3(3) . . ?
C1 N1 S1 112.5(3) . . ?
N1 C1 C2' 100.9(8) . . ?
N1 C1 C2 106.0(5) . . ?
C2' C1 C2 31.2(8) . . ?
N1 C1 H1A 110.5 . . ?
C2' C1 H1A 137.9 . . ?
C2 C1 H1A 110.5 . . ?
N1 C1 H1B 110.5 . . ?
C2' C1 H1B 84.4 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
N1 C1 H1C 111.1 . . ?
C2' C1 H1C 110.9 . . ?
C2 C1 H1C 80.7 . . ?
H1A C1 H1C 31.6 . . ?
H1B C1 H1C 131.3 . . ?
N1 C1 H1D 111.2 . . ?
C2' C1 H1D 111.2 . . ?
C2 C1 H1D 132.4 . . ?
H1A C1 H1D 83.1 . . ?
H1B C1 H1D 28.0 . . ?
H1C C1 H1D 111.1 . . ?
C4 C2 C3 113.2(10) . . ?
C4 C2 C1 111.1(7) . . ?
C3 C2 C1 102.2(10) . . ?
C4 C2 H2 110.1 . . ?
C3 C2 H2 110.1 . . ?
C1 C2 H2 110.1 . . ?
O3 C3 C2 99.2(12) . . ?
O3 C3 H3A 111.9 . . ?
C2 C3 H3A 111.9 . . ?
O3 C3 H3B 111.9 . . ?
C2 C3 H3B 111.9 . . ?
H3A C3 H3B 109.6 . . ?
C3' C2' C4 126(2) . . ?
C3' C2' C1 96.0(17) . . ?
C4 C2' C1 114.9(15) . . ?
C3' C2' H2' 106.1 . . ?
C4 C2' H2' 106.1 . . ?
C1 C2' H2' 106.1 . . ?
O3 C3' C2' 121(2) . . ?
O3 C3' H3'1 107.2 . . ?
C2' C3' H3'1 107.2 . . ?
O3 C3' H3'2 107.1 . . ?
C2' C3' H3'2 107.1 . . ?
H3'1 C3' H3'2 106.8 . . ?
C5' C4 C5 70.0(7) . . ?
C5' C4 C2 161.9(9) . . ?
C5 C4 C2 127.0(7) . . ?
C5' C4 C2' 129.8(13) . . ?
C5 C4 C2' 159.4(11) . . ?
C2 C4 C2' 32.6(7) . . ?
C5' C4 H4 47.0 . . ?
C5 C4 H4 116.5 . . ?
C2 C4 H4 116.5 . . ?
C2' C4 H4 84.0 . . ?
C5' C4 H4' 102.9 . . ?
C5 C4 H4' 35.3 . . ?
C2 C4 H4' 95.1 . . ?
C2' C4 H4' 126.9 . . ?
H4 C4 H4' 144.6 . . ?
C4 C5 C6 131.2(9) . . ?
C4 C5 H4' 48.1 . . ?
C6 C5 H4' 155.4 . . ?
C4 C5 H5 114.4 . . ?
C6 C5 H5 114.4 . . ?
H4' C5 H5 73.0 . . ?
C11 C6 C7 119(2) . . ?
C11 C6 C5 121(2) . . ?
C7 C6 C5 120.2(13) . . ?
C6 C7 C8 118.2(15) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C9 C8 C7 119.7(19) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C9 C10 C11 116.4(14) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 H10 121.8 . . ?
C6 C11 C10 123(2) . . ?
C6 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C4 C5' C6' 131.2(16) . . ?
C4 C5' H5' 114.4 . . ?
C6' C5' H5' 114.4 . . ?
C11' C6' C7' 120(2) . . ?
C11' C6' C5' 128(2) . . ?
C7' C6' C5' 112(3) . . ?
C8' C7' C6' 122(3) . . ?
C8' C7' H7' 119.0 . . ?
C6' C7' H7' 119.1 . . ?
C7' C8' C9 119(3) . . ?
C7' C8' H8' 120.3 . . ?
C9 C8' H8' 120.3 . . ?
C9 C10' C11' 118(3) . . ?
C9 C10' H10' 120.8 . . ?
C11' C10' H10' 120.8 . . ?
C6' C11' C10' 119(2) . . ?
C6' C11' H11' 120.4 . . ?
C10' C11' H11' 120.4 . . ?
C10 C9 C8 123.7(12) . . ?
C10 C9 C8' 138(2) . . ?
C8 C9 C8' 17(3) . . ?
C10 C9 C10' 17.6(13) . . ?
C8 C9 C10' 106.5(15) . . ?
C8' C9 C10' 121(2) . . ?
C10 C9 Br1' 97.6(8) . . ?
C8 C9 Br1' 138.5(11) . . ?
C8' C9 Br1' 123.7(18) . . ?
C10' C9 Br1' 115.0(12) . . ?
C10 C9 Br1 117.4(8) . . ?
C8 C9 Br1 118.5(11) . . ?
C8' C9 Br1 104.1(18) . . ?
C10' C9 Br1 134.9(11) . . ?
Br1' C9 Br1 20.0(2) . . ?
C17 C12 C13 120.5(4) . . ?
C17 C12 S1 119.9(3) . . ?
C13 C12 S1 119.3(4) . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.6(4) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 118.0(4) . . ?
C16 C15 C18 120.4(5) . . ?
C14 C15 C18 121.6(4) . . ?
C15 C16 C17 121.3(5) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C12 C17 C16 119.5(4) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C3' O3 N1 C1 -9.2(17) . . . . ?
C3 O3 N1 C1 -22.6(9) . . . . ?
C3' O3 N1 S1 111.7(17) . . . . ?
C3 O3 N1 S1 98.3(9) . . . . ?
O2 S1 N1 O3 -49.5(3) . . . . ?
O1 S1 N1 O3 -179.1(3) . . . . ?
C12 S1 N1 O3 67.5(3) . . . . ?
O2 S1 N1 C1 67.7(4) . . . . ?
O1 S1 N1 C1 -61.9(4) . . . . ?
C12 S1 N1 C1 -175.3(3) . . . . ?
O3 N1 C1 C2' 28.4(11) . . . . ?
S1 N1 C1 C2' -89.1(11) . . . . ?
O3 N1 C1 C2 -3.4(6) . . . . ?
S1 N1 C1 C2 -120.8(5) . . . . ?
N1 C1 C2 C4 147.6(6) . . . . ?
C2' C1 C2 C4 63.0(17) . . . . ?
N1 C1 C2 C3 26.7(11) . . . . ?
C2' C1 C2 C3 -58.0(18) . . . . ?
C3' O3 C3 C2 -22(7) . . . . ?
N1 O3 C3 C2 38.6(14) . . . . ?
C4 C2 C3 O3 -157.2(9) . . . . ?
C1 C2 C3 O3 -37.7(13) . . . . ?
N1 C1 C2' C3' -34(2) . . . . ?
C2 C1 C2' C3' 69(2) . . . . ?
N1 C1 C2' C4 -168.5(13) . . . . ?
C2 C1 C2' C4 -65.6(19) . . . . ?
N1 O3 C3' C2' -18(4) . . . . ?
C3 O3 C3' C2' 105(9) . . . . ?
C4 C2' C3' O3 162(2) . . . . ?
C1 C2' C3' O3 35(4) . . . . ?
C3 C2 C4 C5' 37(3) . . . . ?
C1 C2 C4 C5' -77(3) . . . . ?
C3 C2 C4 C5 -120.8(12) . . . . ?
C1 C2 C4 C5 125.0(8) . . . . ?
C3 C2 C4 C2' 54.2(17) . . . . ?
C1 C2 C4 C2' -60.0(17) . . . . ?
C3' C2' C4 C5' 124(3) . . . . ?
C1 C2' C4 C5' -117.6(17) . . . . ?
C3' C2' C4 C5 -38(5) . . . . ?
C1 C2' C4 C5 81(3) . . . . ?
C3' C2' C4 C2 -49(3) . . . . ?
C1 C2' C4 C2 69(2) . . . . ?
C5' C4 C5 C6 10.9(13) . . . . ?
C2 C4 C5 C6 -176.3(11) . . . . ?
C2' C4 C5 C6 176(2) . . . . ?
C4 C5 C6 C11 179.3(13) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C11 C6 C7 C8 -3(3) . . . . ?
C5 C6 C7 C8 177.9(17) . . . . ?
C6 C7 C8 C9 5(3) . . . . ?
C7 C6 C11 C10 3(3) . . . . ?
C5 C6 C11 C10 -178.0(17) . . . . ?
C9 C10 C11 C6 -4(4) . . . . ?
C5 C4 C5' C6' -9.2(16) . . . . ?
C2 C4 C5' C6' -171(2) . . . . ?
C2' C4 C5' C6' 177.4(16) . . . . ?
C4 C5' C6' C11' 15(3) . . . . ?
C4 C5' C6' C7' -166.8(18) . . . . ?
C11' C6' C7' C8' 1(4) . . . . ?
C5' C6' C7' C8' -178(3) . . . . ?
C6' C7' C8' C9 -6(6) . . . . ?
C7' C6' C11' C10' 1(4) . . . . ?
C5' C6' C11' C10' 179(3) . . . . ?
C9 C10' C11' C6' 2(5) . . . . ?
C11 C10 C9 C8 6(3) . . . . ?
C11 C10 C9 C8' -4(5) . . . . ?
C11 C10 C9 C10' -8(7) . . . . ?
C11 C10 C9 Br1' -178(2) . . . . ?
C11 C10 C9 Br1 178.7(16) . . . . ?
C7 C8 C9 C10 -7(3) . . . . ?
C7 C8 C9 C8' 149(14) . . . . ?
C7 C8 C9 C10' -2(3) . . . . ?
C7 C8 C9 Br1' 179.5(10) . . . . ?
C7 C8 C9 Br1 -179.1(16) . . . . ?
C7' C8' C9 C10 7(7) . . . . ?
C7' C8' C9 C8 -24(8) . . . . ?
C7' C8' C9 C10' 9(6) . . . . ?
C7' C8' C9 Br1' 180(3) . . . . ?
C7' C8' C9 Br1 -175(4) . . . . ?
C11' C10' C9 C10 171(12) . . . . ?
C11' C10' C9 C8 3(4) . . . . ?
C11' C10' C9 C8' -7(5) . . . . ?
C11' C10' C9 Br1' -179(2) . . . . ?
C11' C10' C9 Br1 178.5(17) . . . . ?
O2 S1 C12 C17 0.2(5) . . . . ?
O1 S1 C12 C17 130.0(4) . . . . ?
N1 S1 C12 C17 -120.7(4) . . . . ?
O2 S1 C12 C13 -174.1(4) . . . . ?
O1 S1 C12 C13 -44.3(4) . . . . ?
N1 S1 C12 C13 64.9(4) . . . . ?
C17 C12 C13 C14 -1.9(7) . . . . ?
S1 C12 C13 C14 172.4(4) . . . . ?
C12 C13 C14 C15 -1.6(7) . . . . ?
C13 C14 C15 C16 3.8(7) . . . . ?
C13 C14 C15 C18 -176.1(5) . . . . ?
C14 C15 C16 C17 -2.6(7) . . . . ?
C18 C15 C16 C17 177.3(5) . . . . ?
C13 C12 C17 C16 3.1(7) . . . . ?
S1 C12 C17 C16 -171.2(4) . . . . ?
C15 C16 C17 C12 -0.8(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.056