# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Ming-Hua Xu'
_publ_contact_author_email       XUMH@MAIL.SHCNC.AC.CN

_publ_section_title              
;
Highly Diasteroselective Friedel-Crafts Reaction
of Indoles with N-tert-Butanesulfinylimino Ester: An Efficient and
Practical Approach to Enantiomerically Enriched ?-(3-Indolyl)glycines
;
loop_
_publ_author_name
'Ming-Hua Xu'
'Du-Ming Ji'

# Attachment 'Crystal_3e-CCDC_740797.cif'

data_cd29260
_database_code_depnum_ccdc_archive 'CCDC 740797'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 Br N2 O3 S'
_chemical_formula_weight         477.41

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'
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           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                   10.7973(14)
_cell_length_b                   14.2880(18)
_cell_length_c                   15.311(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2362.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      4.616
_cell_measurement_theta_max      37.590

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6225
_exptl_absorpt_correction_T_max  1.0000
_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            12471
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0902
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4407
_reflns_number_gt                1646
_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
[0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.1352P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_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   0.07(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4407
_refine_ls_number_parameters     255
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.2290
_refine_ls_wR_factor_gt          0.1940
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.929
_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
H2 H 0.718(7) 0.230(3) 0.263(5) 0.09(3) Uiso 1 1 d D . .
Br Br 1.17682(11) -0.02361(14) 0.30818(9) 0.1811(8) Uani 1 1 d . . .
S1 S 0.84277(19) 0.17237(19) 0.36398(14) 0.1007(8) Uani 1 1 d . . .
O1 O 0.6443(15) 0.2154(10) 0.1273(10) 0.248(6) Uiso 1 1 d . . .
O2 O 0.7546(6) 0.1198(6) 0.0509(3) 0.127(2) Uani 1 1 d D . .
O3 O 0.9445(6) 0.2443(6) 0.3600(5) 0.145(3) Uani 1 1 d . . .
N1 N 0.9163(6) -0.1116(7) 0.2047(4) 0.0872(19) Uani 1 1 d . . .
H1A H 0.9693 -0.1560 0.1980 0.105 Uiso 1 1 calc R . .
N2 N 0.7524(7) 0.1762(7) 0.2758(4) 0.104(2) Uani 1 1 d D . .
C1 C 0.8041(7) 0.1339(8) 0.1966(5) 0.098(3) Uani 1 1 d . . .
H1 H 0.8840 0.1642 0.1856 0.117 Uiso 1 1 calc R . .
C2 C 0.8285(7) 0.0301(7) 0.2070(4) 0.081(2) Uani 1 1 d . . .
C3 C 0.9358(6) -0.0177(9) 0.1881(5) 0.091(3) Uani 1 1 d . . .
C4 C 0.8036(7) -0.1205(8) 0.2321(4) 0.080(2) Uani 1 1 d . . .
C5 C 0.7387(6) -0.0371(7) 0.2340(4) 0.079(2) Uani 1 1 d . . .
C6 C 0.6147(7) -0.0335(9) 0.2609(5) 0.099(3) Uani 1 1 d . . .
H6 H 0.5728 0.0233 0.2628 0.119 Uiso 1 1 calc R . .
C7 C 0.5563(9) -0.1142(12) 0.2844(6) 0.119(4) Uani 1 1 d . . .
H7 H 0.4740 -0.1119 0.3021 0.143 Uiso 1 1 calc R . .
C8 C 0.6178(9) -0.2010(9) 0.2824(6) 0.109(3) Uani 1 1 d . . .
H8 H 0.5771 -0.2555 0.2990 0.131 Uiso 1 1 calc R . .
C9 C 0.7456(9) -0.2040(9) 0.2540(5) 0.104(3) Uani 1 1 d . . .
H9 H 0.7879 -0.2605 0.2505 0.125 Uiso 1 1 calc R . .
C10 C 0.7316(9) 0.2186(9) 0.4424(5) 0.110(3) Uani 1 1 d . . .
C11 C 0.6272(10) 0.1446(8) 0.4522(8) 0.140(4) Uani 1 1 d . . .
H11A H 0.6603 0.0890 0.4786 0.211 Uiso 1 1 calc R . .
H11B H 0.5943 0.1296 0.3957 0.211 Uiso 1 1 calc R . .
H11C H 0.5625 0.1693 0.4884 0.211 Uiso 1 1 calc R . .
C12 C 0.6842(13) 0.3126(9) 0.4176(7) 0.151(4) Uani 1 1 d . . .
H12A H 0.6381 0.3386 0.4654 0.226 Uiso 1 1 calc R . .
H12B H 0.6313 0.3070 0.3674 0.226 Uiso 1 1 calc R . .
H12C H 0.7526 0.3529 0.4038 0.226 Uiso 1 1 calc R . .
C13 C 0.8006(12) 0.2228(12) 0.5281(7) 0.186(6) Uani 1 1 d . . .
H13A H 0.8638 0.2699 0.5248 0.279 Uiso 1 1 calc R . .
H13B H 0.8379 0.1631 0.5397 0.279 Uiso 1 1 calc R . .
H13C H 0.7438 0.2381 0.5742 0.279 Uiso 1 1 calc R . .
C14 C 0.7284(14) 0.1560(9) 0.1293(6) 0.149(5) Uani 1 1 d D . .
C15 C 0.7040(14) 0.1457(11) -0.0300(10) 0.178(6) Uiso 1 1 d D . .
H15A H 0.7596 0.1300 -0.0776 0.214 Uiso 1 1 calc R . .
H15B H 0.6862 0.2122 -0.0319 0.214 Uiso 1 1 calc R . .
C16 C 0.5897(17) 0.0902(11) -0.0344(12) 0.215(7) Uiso 1 1 d D . .
H16A H 0.5929 0.0412 0.0083 0.322 Uiso 1 1 calc R . .
H16B H 0.5817 0.0634 -0.0916 0.322 Uiso 1 1 calc R . .
H16C H 0.5199 0.1299 -0.0229 0.322 Uiso 1 1 calc R . .
C17 C 1.0521(7) 0.0197(7) 0.1511(5) 0.094(3) Uani 1 1 d . . .
C18 C 1.0535(10) 0.0532(7) 0.0666(7) 0.118(3) Uani 1 1 d . . .
H18 H 0.9791 0.0529 0.0359 0.142 Uiso 1 1 calc R . .
C19 C 1.1558(13) 0.0867(9) 0.0247(8) 0.141(4) Uani 1 1 d . . .
H19 H 1.1510 0.1072 -0.0328 0.169 Uiso 1 1 calc R . .
C20 C 1.2620(12) 0.0893(10) 0.0676(10) 0.148(5) Uani 1 1 d . . .
H20 H 1.3309 0.1163 0.0414 0.178 Uiso 1 1 calc R . .
C21 C 1.2722(9) 0.0529(9) 0.1503(10) 0.138(4) Uani 1 1 d . . .
H21 H 1.3489 0.0496 0.1777 0.166 Uiso 1 1 calc R . .
C22 C 1.1634(7) 0.0203(7) 0.1933(6) 0.109(3) Uani 1 1 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
Br 0.0783(7) 0.333(2) 0.1321(10) 0.0508(11) -0.0256(6) -0.0006(10)
S1 0.0632(11) 0.163(2) 0.0759(13) 0.0079(13) 0.0056(10) -0.0257(15)
O2 0.133(5) 0.187(6) 0.061(3) 0.006(4) 0.002(3) 0.027(5)
O3 0.091(4) 0.206(7) 0.137(5) 0.002(5) 0.018(4) -0.062(5)
N1 0.047(4) 0.135(6) 0.080(4) 0.012(5) 0.002(3) 0.014(4)
N2 0.085(5) 0.164(8) 0.062(4) 0.000(5) 0.012(3) 0.042(5)
C1 0.070(5) 0.169(10) 0.055(4) 0.005(5) 0.008(4) 0.017(6)
C2 0.063(5) 0.125(7) 0.053(4) 0.010(4) 0.011(3) 0.026(6)
C3 0.049(4) 0.161(9) 0.064(4) 0.007(6) 0.015(3) 0.015(5)
C4 0.055(5) 0.129(8) 0.055(4) 0.006(5) 0.000(3) -0.015(6)
C5 0.038(4) 0.140(8) 0.059(4) 0.016(5) 0.007(3) 0.009(5)
C6 0.051(4) 0.176(10) 0.071(5) -0.002(6) 0.002(3) 0.002(6)
C7 0.060(5) 0.216(12) 0.081(6) -0.013(7) 0.009(4) 0.007(8)
C8 0.074(6) 0.171(11) 0.082(6) 0.009(6) 0.015(4) -0.015(7)
C9 0.080(6) 0.165(11) 0.068(5) 0.001(6) -0.004(4) 0.028(7)
C10 0.098(7) 0.162(11) 0.069(5) -0.004(6) 0.003(5) -0.035(7)
C11 0.104(8) 0.168(10) 0.150(9) -0.006(8) 0.045(7) -0.043(7)
C12 0.192(12) 0.141(10) 0.120(9) -0.028(7) 0.054(8) -0.001(11)
C13 0.155(11) 0.312(18) 0.091(8) -0.018(9) 0.002(7) -0.070(13)
C14 0.197(12) 0.192(12) 0.059(6) -0.013(7) 0.023(7) 0.061(10)
C17 0.067(5) 0.144(8) 0.071(5) -0.006(5) 0.020(4) 0.017(5)
C18 0.097(7) 0.146(9) 0.111(7) 0.006(6) 0.033(5) -0.008(6)
C19 0.103(9) 0.207(13) 0.113(8) 0.002(7) 0.036(7) -0.021(9)
C20 0.105(10) 0.195(13) 0.145(11) -0.007(9) 0.073(9) -0.020(8)
C21 0.061(5) 0.182(11) 0.172(12) -0.027(10) 0.039(7) 0.003(6)
C22 0.056(5) 0.153(8) 0.118(7) -0.031(6) 0.010(5) 0.010(5)

_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
Br C22 1.874(10) . ?
S1 O3 1.505(6) . ?
S1 N2 1.667(7) . ?
S1 C10 1.822(10) . ?
O1 C14 1.243(16) . ?
O2 C14 1.337(10) . ?
O2 C15 1.404(15) . ?
N1 C4 1.293(9) . ?
N1 C3 1.382(11) . ?
N1 H1A 0.8600 . ?
N2 C1 1.464(11) . ?
N2 H2 0.88(2) . ?
C1 C14 1.354(14) . ?
C1 C2 1.514(12) . ?
C1 H1 0.9800 . ?
C2 C3 1.376(11) . ?
C2 C5 1.426(11) . ?
C3 C17 1.478(12) . ?
C4 C5 1.382(12) . ?
C4 C9 1.389(13) . ?
C5 C6 1.402(10) . ?
C6 C7 1.362(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.407(15) . ?
C7 H7 0.9300 . ?
C8 C9 1.447(13) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C12 1.487(15) . ?
C10 C13 1.510(14) . ?
C10 C11 1.553(13) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.468(14) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.364(12) . ?
C17 C18 1.380(12) . ?
C18 C19 1.364(13) . ?
C18 H18 0.9300 . ?
C19 C20 1.322(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(17) . ?
C20 H20 0.9300 . ?
C21 C22 1.425(13) . ?
C21 H21 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
O3 S1 N2 111.8(5) . . ?
O3 S1 C10 105.1(5) . . ?
N2 S1 C10 97.8(4) . . ?
C14 O2 C15 127.4(10) . . ?
C4 N1 C3 107.3(8) . . ?
C4 N1 H1A 126.3 . . ?
C3 N1 H1A 126.3 . . ?
C1 N2 S1 115.7(6) . . ?
C1 N2 H2 110(5) . . ?
S1 N2 H2 117(6) . . ?
C14 C1 N2 107.7(8) . . ?
C14 C1 C2 114.4(9) . . ?
N2 C1 C2 112.5(7) . . ?
C14 C1 H1 107.3 . . ?
N2 C1 H1 107.3 . . ?
C2 C1 H1 107.3 . . ?
C3 C2 C5 107.4(9) . . ?
C3 C2 C1 127.6(8) . . ?
C5 C2 C1 124.9(7) . . ?
C2 C3 N1 108.4(8) . . ?
C2 C3 C17 128.1(10) . . ?
N1 C3 C17 123.5(8) . . ?
N1 C4 C5 113.6(9) . . ?
N1 C4 C9 125.9(11) . . ?
C5 C4 C9 120.4(7) . . ?
C4 C5 C6 121.5(9) . . ?
C4 C5 C2 103.3(7) . . ?
C6 C5 C2 135.2(10) . . ?
C7 C6 C5 119.3(11) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 121.4(9) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 118.9(10) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C4 C9 C8 118.5(10) . . ?
C4 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C12 C10 C13 110.8(11) . . ?
C12 C10 C11 113.0(10) . . ?
C13 C10 C11 107.5(9) . . ?
C12 C10 S1 112.7(7) . . ?
C13 C10 S1 105.2(8) . . ?
C11 C10 S1 107.2(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 O2 113.4(12) . . ?
O1 C14 C1 128.2(11) . . ?
O2 C14 C1 117.7(10) . . ?
O2 C15 C16 103.0(13) . . ?
O2 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
O2 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 115.6(8) . . ?
C22 C17 C3 124.7(8) . . ?
C18 C17 C3 119.6(8) . . ?
C19 C18 C17 124.8(11) . . ?
C19 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
C20 C19 C18 118.7(12) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 121.2(11) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 118.9(11) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C17 C22 C21 120.6(10) . . ?
C17 C22 Br 120.7(7) . . ?
C21 C22 Br 118.7(8) . . ?

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
O3 S1 N2 C1 76.7(9) . . . . ?
C10 S1 N2 C1 -173.5(9) . . . . ?
S1 N2 C1 C14 -170.5(9) . . . . ?
S1 N2 C1 C2 62.5(10) . . . . ?
C14 C1 C2 C3 107.0(10) . . . . ?
N2 C1 C2 C3 -129.7(8) . . . . ?
C14 C1 C2 C5 -68.8(10) . . . . ?
N2 C1 C2 C5 54.5(10) . . . . ?
C5 C2 C3 N1 -1.7(8) . . . . ?
C1 C2 C3 N1 -178.1(6) . . . . ?
C5 C2 C3 C17 174.8(7) . . . . ?
C1 C2 C3 C17 -1.6(13) . . . . ?
C4 N1 C3 C2 0.1(8) . . . . ?
C4 N1 C3 C17 -176.6(7) . . . . ?
C3 N1 C4 C5 1.7(9) . . . . ?
C3 N1 C4 C9 178.3(8) . . . . ?
N1 C4 C5 C6 179.3(6) . . . . ?
C9 C4 C5 C6 2.4(11) . . . . ?
N1 C4 C5 C2 -2.6(8) . . . . ?
C9 C4 C5 C2 -179.4(7) . . . . ?
C3 C2 C5 C4 2.5(8) . . . . ?
C1 C2 C5 C4 179.0(6) . . . . ?
C3 C2 C5 C6 -179.8(8) . . . . ?
C1 C2 C5 C6 -3.2(12) . . . . ?
C4 C5 C6 C7 -1.1(11) . . . . ?
C2 C5 C6 C7 -178.6(8) . . . . ?
C5 C6 C7 C8 0.2(12) . . . . ?
C6 C7 C8 C9 -0.5(13) . . . . ?
N1 C4 C9 C8 -179.1(7) . . . . ?
C5 C4 C9 C8 -2.7(11) . . . . ?
C7 C8 C9 C4 1.8(12) . . . . ?
O3 S1 C10 C12 57.7(9) . . . . ?
N2 S1 C10 C12 -57.6(9) . . . . ?
O3 S1 C10 C13 -63.2(9) . . . . ?
N2 S1 C10 C13 -178.4(9) . . . . ?
O3 S1 C10 C11 -177.5(7) . . . . ?
N2 S1 C10 C11 67.3(8) . . . . ?
C15 O2 C14 O1 4(2) . . . . ?
C15 O2 C14 C1 -167.5(12) . . . . ?
N2 C1 C14 O1 13(2) . . . . ?
C2 C1 C14 O1 139.3(15) . . . . ?
N2 C1 C14 O2 -176.3(11) . . . . ?
C2 C1 C14 O2 -50.4(14) . . . . ?
C14 O2 C15 C16 -85.2(16) . . . . ?
C2 C3 C17 C22 116.3(10) . . . . ?
N1 C3 C17 C22 -67.7(13) . . . . ?
C2 C3 C17 C18 -66.8(13) . . . . ?
N1 C3 C17 C18 109.2(10) . . . . ?
C22 C17 C18 C19 -0.8(16) . . . . ?
C3 C17 C18 C19 -177.9(11) . . . . ?
C17 C18 C19 C20 -1.2(19) . . . . ?
C18 C19 C20 C21 5(2) . . . . ?
C19 C20 C21 C22 -6(2) . . . . ?
C18 C17 C22 C21 -0.7(14) . . . . ?
C3 C17 C22 C21 176.3(10) . . . . ?
C18 C17 C22 Br -179.6(7) . . . . ?
C3 C17 C22 Br -2.7(14) . . . . ?
C20 C21 C22 C17 4.1(16) . . . . ?
C20 C21 C22 Br -176.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 1.92 2.734(10) 157.6 3_745

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.068

# Attachment 'Crystal_3l-CCDC_740822.cif'

data_cd29248
_database_code_depnum_ccdc_archive 'CCDC 740822'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 Br N2 O3 S'
_chemical_formula_weight         401.32

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)

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

_cell_length_a                   9.3558(14)
_cell_length_b                   9.4206(14)
_cell_length_c                   10.6930(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.473(3)
_cell_angle_gamma                90.00
_cell_volume                     929.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1947
_cell_measurement_theta_min      4.414
_cell_measurement_theta_max      47.471

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    2.338
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.79731
_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            5119
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3425
_reflns_number_gt                2631
_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^)+(0.0632P)^2^+0.0000P] 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    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   0.011(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3425
_refine_ls_number_parameters     220
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_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
Br Br 0.93573(5) 0.74219(6) 1.16272(4) 0.0671(2) Uani 1 1 d . . .
S1 S 0.79468(11) 0.24311(14) 0.52831(9) 0.0493(3) Uani 1 1 d . . .
N1 N 0.6943(5) 0.8361(4) 0.6178(4) 0.0445(11) Uani 1 1 d D . .
N2 N 0.7133(5) 0.3985(4) 0.5389(4) 0.0433(9) Uani 1 1 d D . .
O1 O 0.4683(4) 0.3747(4) 0.6552(3) 0.0571(9) Uani 1 1 d . . .
O2 O 0.6102(4) 0.3798(4) 0.8434(3) 0.0605(9) Uani 1 1 d . . .
O3 O 0.6956(5) 0.1256(4) 0.5484(4) 0.0787(13) Uani 1 1 d . . .
C1 C 0.7149(4) 0.4485(4) 0.6676(4) 0.0349(9) Uani 1 1 d . . .
H1 H 0.8018 0.4108 0.7210 0.042 Uiso 1 1 calc R . .
C2 C 0.7209(5) 0.6080(4) 0.6746(4) 0.0350(10) Uani 1 1 d . . .
C3 C 0.6794(5) 0.6983(4) 0.5760(5) 0.0409(11) Uani 1 1 d . . .
H3 H 0.6461 0.6708 0.4927 0.049 Uiso 1 1 calc R . .
C4 C 0.7482(5) 0.8355(4) 0.7432(5) 0.0368(11) Uani 1 1 d . . .
C5 C 0.7654(4) 0.6922(4) 0.7842(4) 0.0338(11) Uani 1 1 d . . .
C6 C 0.8232(5) 0.6636(5) 0.9110(5) 0.0406(10) Uani 1 1 d . . .
H6 H 0.8364 0.5708 0.9405 0.049 Uiso 1 1 calc R . .
C7 C 0.8594(4) 0.7761(5) 0.9895(4) 0.0460(12) Uani 1 1 d . . .
C8 C 0.8432(5) 0.9179(5) 0.9489(5) 0.0506(12) Uani 1 1 d . . .
H8 H 0.8714 0.9911 1.0060 0.061 Uiso 1 1 calc R . .
C9 C 0.7867(5) 0.9485(5) 0.8271(5) 0.0471(11) Uani 1 1 d . . .
H9 H 0.7739 1.0421 0.7998 0.057 Uiso 1 1 calc R . .
C10 C 0.8020(4) 0.2432(7) 0.3586(4) 0.0537(11) Uani 1 1 d . . .
C11 C 0.8962(9) 0.3675(9) 0.3322(8) 0.101(3) Uani 1 1 d . . .
H11A H 0.9891 0.3605 0.3855 0.152 Uiso 1 1 calc R . .
H11B H 0.8503 0.4548 0.3495 0.152 Uiso 1 1 calc R . .
H11C H 0.9086 0.3656 0.2448 0.152 Uiso 1 1 calc R . .
C12 C 0.6506(5) 0.2557(9) 0.2822(4) 0.0743(15) Uani 1 1 d . . .
H12A H 0.6557 0.2489 0.1934 0.111 Uiso 1 1 calc R . .
H12B H 0.6095 0.3456 0.2992 0.111 Uiso 1 1 calc R . .
H12C H 0.5910 0.1805 0.3055 0.111 Uiso 1 1 calc R . .
C13 C 0.8692(8) 0.1003(8) 0.3361(7) 0.095(2) Uani 1 1 d . . .
H13A H 0.8011 0.0259 0.3443 0.143 Uiso 1 1 calc R . .
H13B H 0.9552 0.0865 0.3975 0.143 Uiso 1 1 calc R . .
H13C H 0.8936 0.0982 0.2524 0.143 Uiso 1 1 calc R . .
C14 C 0.5833(5) 0.3949(4) 0.7190(4) 0.0407(10) Uani 1 1 d . . .
C15 C 0.4930(8) 0.3294(7) 0.9064(6) 0.0730(19) Uani 1 1 d . . .
H15A H 0.4017 0.3679 0.8639 0.088 Uiso 1 1 calc R . .
H15B H 0.5085 0.3626 0.9934 0.088 Uiso 1 1 calc R . .
C16 C 0.4859(8) 0.1744(7) 0.9047(9) 0.106(3) Uani 1 1 d . . .
H16A H 0.4632 0.1419 0.8186 0.159 Uiso 1 1 calc R . .
H16B H 0.4121 0.1433 0.9511 0.159 Uiso 1 1 calc R . .
H16C H 0.5778 0.1362 0.9433 0.159 Uiso 1 1 calc R . .
H1A H 0.690(5) 0.909(3) 0.579(4) 0.045(13) Uiso 1 1 d D . .
H2 H 0.634(3) 0.404(5) 0.494(4) 0.054(15) 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
Br 0.0767(3) 0.0613(3) 0.0544(3) -0.0139(3) -0.0149(2) 0.0058(3)
S1 0.0635(7) 0.0333(6) 0.0484(5) -0.0014(7) 0.0015(4) 0.0136(8)
N1 0.059(3) 0.023(2) 0.050(3) 0.0121(19) 0.008(2) 0.003(2)
N2 0.057(3) 0.030(2) 0.040(2) -0.0008(17) -0.0012(19) 0.0080(18)
O1 0.0477(19) 0.062(2) 0.057(2) -0.0064(16) -0.0049(16) -0.0077(17)
O2 0.067(2) 0.067(3) 0.047(2) 0.0077(16) 0.0083(16) -0.0144(19)
O3 0.140(4) 0.0254(18) 0.076(3) 0.0078(18) 0.033(3) -0.004(2)
C1 0.040(2) 0.024(2) 0.038(2) 0.0002(17) 0.0003(17) 0.0053(17)
C2 0.038(2) 0.030(2) 0.037(2) 0.001(2) 0.0042(19) 0.0004(19)
C3 0.046(3) 0.033(3) 0.042(2) -0.0003(18) 0.003(2) 0.0005(19)
C4 0.035(2) 0.028(2) 0.048(3) -0.003(2) 0.009(2) -0.0025(19)
C5 0.031(2) 0.027(2) 0.044(3) -0.0020(17) 0.0070(19) 0.0003(16)
C6 0.039(2) 0.028(2) 0.053(3) 0.001(2) 0.004(2) 0.0033(18)
C7 0.040(2) 0.050(3) 0.047(2) -0.004(2) 0.0011(18) -0.002(2)
C8 0.049(3) 0.034(3) 0.070(3) -0.015(2) 0.012(2) -0.008(2)
C9 0.049(3) 0.027(2) 0.066(3) -0.002(2) 0.013(2) -0.001(2)
C10 0.056(3) 0.056(3) 0.053(2) -0.010(3) 0.0178(19) 0.000(3)
C11 0.097(6) 0.117(7) 0.102(6) -0.014(5) 0.055(5) -0.041(5)
C12 0.074(3) 0.095(4) 0.051(3) -0.016(4) 0.001(2) 0.004(4)
C13 0.109(6) 0.091(5) 0.095(5) -0.035(5) 0.040(5) 0.021(5)
C14 0.056(3) 0.022(2) 0.043(2) -0.0009(18) 0.004(2) 0.001(2)
C15 0.089(5) 0.075(5) 0.061(4) 0.012(3) 0.032(4) 0.012(4)
C16 0.096(6) 0.065(4) 0.177(9) 0.037(5) 0.080(6) 0.013(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
Br C7 1.900(4) . ?
S1 O3 1.482(4) . ?
S1 N2 1.663(4) . ?
S1 C10 1.828(4) . ?
N1 C4 1.352(6) . ?
N1 C3 1.373(6) . ?
N1 H1A 0.801(19) . ?
N2 C1 1.453(5) . ?
N2 H2 0.815(19) . ?
O1 C14 1.191(5) . ?
O2 C14 1.320(5) . ?
O2 C15 1.458(7) . ?
C1 C2 1.504(6) . ?
C1 C14 1.515(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.360(6) . ?
C2 C5 1.420(6) . ?
C3 H3 0.9300 . ?
C4 C9 1.400(6) . ?
C4 C5 1.421(6) . ?
C5 C6 1.401(7) . ?
C6 C7 1.360(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.405(7) . ?
C8 C9 1.354(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C12 1.518(6) . ?
C10 C11 1.519(9) . ?
C10 C13 1.522(9) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.461(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O3 S1 N2 110.1(2) . . ?
O3 S1 C10 105.7(3) . . ?
N2 S1 C10 99.2(2) . . ?
C4 N1 C3 108.7(4) . . ?
C4 N1 H1A 120(3) . . ?
C3 N1 H1A 130(3) . . ?
C1 N2 S1 114.6(3) . . ?
C1 N2 H2 114(3) . . ?
S1 N2 H2 113(4) . . ?
C14 O2 C15 117.9(4) . . ?
N2 C1 C2 111.4(3) . . ?
N2 C1 C14 110.7(4) . . ?
C2 C1 C14 109.9(3) . . ?
N2 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C14 C1 H1 108.2 . . ?
C3 C2 C5 107.4(4) . . ?
C3 C2 C1 125.6(4) . . ?
C5 C2 C1 127.0(4) . . ?
C2 C3 N1 109.7(5) . . ?
C2 C3 H3 125.1 . . ?
N1 C3 H3 125.1 . . ?
N1 C4 C9 130.3(4) . . ?
N1 C4 C5 108.3(4) . . ?
C9 C4 C5 121.4(4) . . ?
C6 C5 C2 134.9(4) . . ?
C6 C5 C4 119.2(4) . . ?
C2 C5 C4 105.9(4) . . ?
C7 C6 C5 117.6(4) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C8 123.2(4) . . ?
C6 C7 Br 119.1(3) . . ?
C8 C7 Br 117.7(3) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 118.2(4) . . ?
C8 C9 H9 120.9 . . ?
C4 C9 H9 120.9 . . ?
C12 C10 C11 111.0(6) . . ?
C12 C10 C13 110.9(6) . . ?
C11 C10 C13 112.6(5) . . ?
C12 C10 S1 110.5(3) . . ?
C11 C10 S1 107.6(4) . . ?
C13 C10 S1 103.9(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 O2 124.4(4) . . ?
O1 C14 C1 123.8(4) . . ?
O2 C14 C1 111.7(4) . . ?
O2 C15 C16 110.8(6) . . ?
O2 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O3 S1 N2 C1 81.3(4) . . . . ?
C10 S1 N2 C1 -168.1(3) . . . . ?
S1 N2 C1 C2 147.9(3) . . . . ?
S1 N2 C1 C14 -89.5(4) . . . . ?
N2 C1 C2 C3 22.1(6) . . . . ?
C14 C1 C2 C3 -101.0(5) . . . . ?
N2 C1 C2 C5 -160.2(4) . . . . ?
C14 C1 C2 C5 76.7(5) . . . . ?
C5 C2 C3 N1 -0.5(6) . . . . ?
C1 C2 C3 N1 177.6(4) . . . . ?
C4 N1 C3 C2 1.2(6) . . . . ?
C3 N1 C4 C9 177.5(5) . . . . ?
C3 N1 C4 C5 -1.4(6) . . . . ?
C3 C2 C5 C6 -177.2(5) . . . . ?
C1 C2 C5 C6 4.8(9) . . . . ?
C3 C2 C5 C4 -0.4(6) . . . . ?
C1 C2 C5 C4 -178.4(4) . . . . ?
N1 C4 C5 C6 178.5(4) . . . . ?
C9 C4 C5 C6 -0.5(7) . . . . ?
N1 C4 C5 C2 1.1(6) . . . . ?
C9 C4 C5 C2 -177.9(4) . . . . ?
C2 C5 C6 C7 177.0(5) . . . . ?
C4 C5 C6 C7 0.5(7) . . . . ?
C5 C6 C7 C8 -0.9(7) . . . . ?
C5 C6 C7 Br 179.2(3) . . . . ?
C6 C7 C8 C9 1.3(7) . . . . ?
Br C7 C8 C9 -178.7(4) . . . . ?
C7 C8 C9 C4 -1.3(7) . . . . ?
N1 C4 C9 C8 -177.9(5) . . . . ?
C5 C4 C9 C8 0.9(7) . . . . ?
O3 S1 C10 C12 55.6(5) . . . . ?
N2 S1 C10 C12 -58.4(5) . . . . ?
O3 S1 C10 C11 177.0(4) . . . . ?
N2 S1 C10 C11 63.0(5) . . . . ?
O3 S1 C10 C13 -63.4(4) . . . . ?
N2 S1 C10 C13 -177.4(4) . . . . ?
C15 O2 C14 O1 2.6(7) . . . . ?
C15 O2 C14 C1 179.7(4) . . . . ?
N2 C1 C14 O1 -32.0(6) . . . . ?
C2 C1 C14 O1 91.5(5) . . . . ?
N2 C1 C14 O2 150.9(4) . . . . ?
C2 C1 C14 O2 -85.6(4) . . . . ?
C14 O2 C15 C16 85.0(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.801(19) 2.07(3) 2.827(5) 158(5) 1_565

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.069