# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182

_publ_section_title              
;Organocatalysts Wrapped Around by Polyethylene Glycols
(PEGs): A Unique Host-Guest System for Asymmetric Michael Addition
Reaction
;
_publ_contact_author_name        'Prof. Zhen Yuan Xu'
_publ_contact_author_email       GREENCHEM@ZJUT.EDU.CN
loop_
_publ_author_name
'Zhen Yuan Xu'
'Luo Shu Ping'
'Yi Feng Wang'
'Li Ping Wang'
;
Ai Bao Xia
;
'Dan Qian Xu'
'Hua Dong Yue'

# Attachment 'CCDC 639780.txt'

data_cd2733
_database_code_depnum_ccdc_archive 'CCDC 639780'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 Br N3 O3 S2'
_chemical_formula_weight         450.41

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                   7.022(7)
_cell_length_b                   7.332(8)
_cell_length_c                   38.75(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1995(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3045
_cell_measurement_theta_min      5.654
_cell_measurement_theta_max      46.504

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    2.289
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.56229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_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            11718
_diffrn_reflns_av_R_equivalents  0.1452
_diffrn_reflns_av_sigmaI/netI    0.1212
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4309
_reflns_number_gt                2945
_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^)+(0.0754P)^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     SHELXL
_refine_ls_extinction_coef       0.0047(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4309
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.918
_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 0.43368(12) -0.32068(9) 0.203548(18) 0.0717(3) Uani 1 1 d . . .
S1 S 0.5916(2) 0.15859(16) 0.14831(4) 0.0414(3) Uani 1 1 d . . .
S2 S 0.00494(19) 0.05620(18) 0.08938(3) 0.0380(3) Uani 1 1 d . . .
O1 O 0.0300(9) -0.1104(6) 0.10852(12) 0.0830(18) Uani 1 1 d . . .
O2 O -0.1851(6) 0.0901(9) 0.07888(11) 0.0839(19) Uani 1 1 d . . .
O3 O 0.0868(7) 0.2046(6) 0.10912(10) 0.0587(12) Uani 1 1 d . . .
N1 N 0.1839(6) 0.0146(6) 0.17800(11) 0.0394(10) Uani 1 1 d . . .
H1A H 0.1559 0.0228 0.1554 0.047 Uiso 1 1 calc R . .
H1B H 0.2680 -0.0767 0.1810 0.047 Uiso 1 1 calc R . .
N2 N 0.3995(9) 0.4167(7) 0.11114(13) 0.0444(13) Uani 1 1 d . . .
N3 N 0.6723(6) 0.5142(6) 0.12895(11) 0.0391(10) Uani 1 1 d . . .
C1 C 0.0064(9) -0.0217(9) 0.19852(17) 0.0594(16) Uani 1 1 d . . .
H1C H -0.1050 -0.0191 0.1837 0.071 Uiso 1 1 calc R . .
H1D H 0.0133 -0.1400 0.2097 0.071 Uiso 1 1 calc R . .
C2 C -0.0027(15) 0.1237(13) 0.2241(2) 0.109(5) Uani 1 1 d . . .
H2A H -0.0992 0.2118 0.2176 0.125 Uiso 1 1 calc R . .
H2B H -0.0367 0.0735 0.2464 0.125 Uiso 1 1 calc R . .
C3 C 0.1781(9) 0.2106(10) 0.22615(16) 0.0581(17) Uani 1 1 d . . .
H3A H 0.2571 0.1514 0.2434 0.070 Uiso 1 1 calc R . .
H3B H 0.1633 0.3378 0.2324 0.070 Uiso 1 1 calc R . .
C4 C 0.2679(7) 0.1942(7) 0.19091(13) 0.0372(12) Uani 1 1 d . . .
H4 H 0.2238 0.2944 0.1762 0.045 Uiso 1 1 calc R . .
C5 C 0.4831(8) 0.1884(8) 0.19068(13) 0.0432(12) Uani 1 1 d . . .
H5A H 0.5245 0.0892 0.2055 0.052 Uiso 1 1 calc R . .
H5B H 0.5305 0.3010 0.2006 0.052 Uiso 1 1 calc R . .
C6 C 0.5526(8) 0.3704(7) 0.12926(13) 0.0382(12) Uani 1 1 d . . .
C7 C 0.4200(10) 0.5918(8) 0.09925(15) 0.0520(15) Uani 1 1 d . . .
H7 H 0.3332 0.6569 0.0860 0.062 Uiso 1 1 calc R . .
C8 C 0.5897(10) 0.6509(7) 0.11054(15) 0.0495(14) Uani 1 1 d . . .
H8 H 0.6419 0.7655 0.1065 0.059 Uiso 1 1 calc R . .
C9 C 0.8531(8) 0.5277(9) 0.14791(18) 0.0549(16) Uani 1 1 d . . .
H9A H 0.8278 0.5590 0.1715 0.082 Uiso 1 1 calc R . .
H9B H 0.9312 0.6203 0.1376 0.082 Uiso 1 1 calc R . .
H9C H 0.9182 0.4127 0.1470 0.082 Uiso 1 1 calc R . .
C10 C 0.1483(7) 0.0359(7) 0.05164(13) 0.0378(12) Uani 1 1 d . . .
C11 C 0.0665(10) 0.0456(9) 0.01950(13) 0.0548(15) Uani 1 1 d . . .
H11 H -0.0633 0.0679 0.0172 0.066 Uiso 1 1 calc R . .
C12 C 0.1774(11) 0.0222(10) -0.00906(15) 0.0644(19) Uani 1 1 d . . .
H12 H 0.1217 0.0282 -0.0308 0.077 Uiso 1 1 calc R . .
C13 C 0.3727(10) -0.0106(9) -0.00638(15) 0.0539(16) Uani 1 1 d . . .
C14 C 0.4506(9) -0.0135(8) 0.02629(15) 0.0524(15) Uani 1 1 d . . .
H14 H 0.5810 -0.0320 0.0286 0.063 Uiso 1 1 calc R . .
C15 C 0.3439(8) 0.0094(8) 0.05518(14) 0.0444(13) Uani 1 1 d . . .
H15 H 0.4002 0.0076 0.0769 0.053 Uiso 1 1 calc R . .
C16 C 0.4981(13) -0.0395(11) -0.03815(17) 0.086(3) Uani 1 1 d . . .
H16A H 0.6281 -0.0125 -0.0324 0.109 Uiso 1 1 calc R . .
H16B H 0.4566 0.0398 -0.0564 0.109 Uiso 1 1 calc R . .
H16C H 0.4884 -0.1640 -0.0456 0.109 Uiso 1 1 calc R . .
H2 H 0.319(9) 0.374(8) 0.1082(15) 0.03(2) Uiso 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 0.1004(6) 0.0417(3) 0.0731(5) -0.0014(3) 0.0026(4) 0.0262(4)
S1 0.0440(8) 0.0254(6) 0.0547(7) 0.0002(5) 0.0114(7) 0.0029(6)
S2 0.0389(7) 0.0406(7) 0.0345(6) -0.0011(5) 0.0016(6) -0.0106(6)
O1 0.141(5) 0.045(2) 0.063(3) 0.014(2) 0.041(3) -0.003(3)
O2 0.031(2) 0.165(6) 0.056(3) -0.005(3) 0.001(2) 0.009(3)
O3 0.060(3) 0.059(3) 0.057(2) -0.024(2) 0.014(2) -0.026(2)
N1 0.040(3) 0.041(3) 0.036(2) -0.0007(19) 0.000(2) -0.005(2)
N2 0.044(3) 0.035(2) 0.054(3) 0.002(2) -0.010(3) -0.013(3)
N3 0.038(2) 0.027(2) 0.052(3) -0.0016(19) 0.007(2) -0.005(2)
C1 0.050(4) 0.053(4) 0.075(4) 0.002(3) 0.015(3) -0.006(3)
C2 0.106(8) 0.098(8) 0.102(8) -0.048(7) 0.058(7) -0.045(7)
C3 0.044(4) 0.073(5) 0.057(4) -0.010(3) 0.010(3) 0.003(3)
C4 0.040(3) 0.029(2) 0.043(3) -0.002(2) 0.006(2) -0.001(2)
C5 0.047(3) 0.037(3) 0.046(3) -0.004(2) 0.006(3) -0.006(3)
C6 0.037(3) 0.031(3) 0.047(3) -0.002(2) 0.009(3) -0.005(2)
C7 0.064(4) 0.033(3) 0.059(3) 0.016(2) -0.014(3) -0.011(3)
C8 0.064(4) 0.031(3) 0.053(3) 0.006(2) 0.000(3) -0.010(3)
C9 0.038(3) 0.041(3) 0.086(4) 0.000(3) 0.001(3) -0.007(3)
C10 0.043(3) 0.028(2) 0.042(3) -0.003(2) 0.002(2) -0.005(2)
C11 0.057(4) 0.071(4) 0.036(3) 0.000(3) -0.005(3) -0.004(4)
C12 0.093(6) 0.069(4) 0.032(3) -0.001(3) -0.003(3) 0.001(4)
C13 0.071(5) 0.045(3) 0.046(3) -0.004(3) 0.017(3) -0.003(3)
C14 0.044(3) 0.051(3) 0.062(4) -0.002(3) 0.013(3) -0.001(3)
C15 0.042(3) 0.047(3) 0.044(3) 0.002(2) -0.004(3) -0.001(3)
C16 0.121(7) 0.066(5) 0.071(4) -0.005(4) 0.042(5) 0.000(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 H1B 2.3064 . ?
S1 C6 1.741(5) . ?
S1 C5 1.823(5) . ?
S2 O2 1.417(5) . ?
S2 O1 1.439(5) . ?
S2 O3 1.449(4) . ?
S2 C10 1.782(5) . ?
N1 C1 1.502(7) . ?
N1 C4 1.527(7) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C6 1.328(8) . ?
N2 C7 1.372(7) . ?
N2 H2 0.66(6) . ?
N3 C6 1.348(6) . ?
N3 C8 1.360(7) . ?
N3 C9 1.470(7) . ?
C1 C2 1.458(9) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 C3 1.423(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.509(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.512(8) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C8 1.342(9) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.374(7) . ?
C10 C15 1.393(7) . ?
C11 C12 1.364(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.396(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(8) . ?
C13 C16 1.528(9) . ?
C14 C15 1.358(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
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
C6 S1 C5 102.1(3) . . ?
O2 S2 O1 114.3(4) . . ?
O2 S2 O3 113.2(3) . . ?
O1 S2 O3 108.5(3) . . ?
O2 S2 C10 108.1(3) . . ?
O1 S2 C10 106.4(3) . . ?
O3 S2 C10 105.8(2) . . ?
S2 O3 H1A 93.5 . . ?
C1 N1 C4 107.5(4) . . ?
C1 N1 H1A 110.2 . . ?
C4 N1 H1A 110.2 . . ?
C1 N1 H1B 110.2 . . ?
C4 N1 H1B 110.2 . . ?
H1A N1 H1B 108.5 . . ?
C6 N2 C7 109.4(6) . . ?
C6 N2 H2 132(6) . . ?
C7 N2 H2 118(6) . . ?
C6 N3 C8 108.4(5) . . ?
C6 N3 C9 125.9(5) . . ?
C8 N3 C9 125.5(5) . . ?
C2 C1 N1 105.5(5) . . ?
C2 C1 H1C 110.6 . . ?
N1 C1 H1C 110.6 . . ?
C2 C1 H1D 110.6 . . ?
N1 C1 H1D 110.6 . . ?
H1C C1 H1D 108.8 . . ?
C3 C2 C1 109.0(7) . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C2 C3 C4 106.7(5) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C3 C4 C5 115.2(5) . . ?
C3 C4 N1 101.8(4) . . ?
C5 C4 N1 111.1(4) . . ?
C3 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
N1 C4 H4 109.5 . . ?
C4 C5 S1 115.2(4) . . ?
C4 C5 H5A 108.5 . . ?
S1 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
S1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
N2 C6 N3 107.5(5) . . ?
N2 C6 S1 125.4(4) . . ?
N3 C6 S1 127.1(4) . . ?
C8 C7 N2 106.6(6) . . ?
C8 C7 H7 126.7 . . ?
N2 C7 H7 126.7 . . ?
C7 C8 N3 108.2(5) . . ?
C7 C8 H8 125.9 . . ?
N3 C8 H8 125.9 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 120.6(5) . . ?
C11 C10 S2 120.2(4) . . ?
C15 C10 S2 119.2(4) . . ?
C12 C11 C10 119.3(6) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.5(6) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 117.4(6) . . ?
C14 C13 C16 120.6(6) . . ?
C12 C13 C16 122.0(6) . . ?
C15 C14 C13 122.4(6) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C10 118.7(5) . . ?
C14 C15 H15 120.7 . . ?
C10 C15 H15 120.7 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 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
O2 S2 O3 H1A 123.3 . . . . ?
O1 S2 O3 H1A -4.7 . . . . ?
C10 S2 O3 H1A -118.5 . . . . ?
C4 N1 C1 C2 -4.3(8) . . . . ?
N1 C1 C2 C3 -15.6(11) . . . . ?
C1 C2 C3 C4 29.8(11) . . . . ?
C2 C3 C4 C5 -150.9(7) . . . . ?
C2 C3 C4 N1 -30.6(8) . . . . ?
C1 N1 C4 C3 20.9(5) . . . . ?
C1 N1 C4 C5 143.9(5) . . . . ?
C3 C4 C5 S1 177.4(4) . . . . ?
N1 C4 C5 S1 62.4(5) . . . . ?
C6 S1 C5 C4 72.3(5) . . . . ?
C7 N2 C6 N3 -0.4(6) . . . . ?
C7 N2 C6 S1 -178.2(4) . . . . ?
C8 N3 C6 N2 0.5(6) . . . . ?
C9 N3 C6 N2 175.3(5) . . . . ?
C8 N3 C6 S1 178.3(4) . . . . ?
C9 N3 C6 S1 -7.0(8) . . . . ?
C5 S1 C6 N2 -89.0(5) . . . . ?
C5 S1 C6 N3 93.6(5) . . . . ?
C6 N2 C7 C8 0.1(7) . . . . ?
N2 C7 C8 N3 0.2(7) . . . . ?
C6 N3 C8 C7 -0.5(6) . . . . ?
C9 N3 C8 C7 -175.2(5) . . . . ?
O2 S2 C10 C11 -2.8(6) . . . . ?
O1 S2 C10 C11 120.4(5) . . . . ?
O3 S2 C10 C11 -124.3(5) . . . . ?
O2 S2 C10 C15 177.4(5) . . . . ?
O1 S2 C10 C15 -59.3(5) . . . . ?
O3 S2 C10 C15 55.9(5) . . . . ?
C15 C10 C11 C12 2.5(9) . . . . ?
S2 C10 C11 C12 -177.3(5) . . . . ?
C10 C11 C12 C13 -0.3(10) . . . . ?
C11 C12 C13 C14 -1.7(10) . . . . ?
C11 C12 C13 C16 179.2(7) . . . . ?
C12 C13 C14 C15 1.7(9) . . . . ?
C16 C13 C14 C15 -179.2(6) . . . . ?
C13 C14 C15 C10 0.4(9) . . . . ?
C11 C10 C15 C14 -2.5(9) . . . . ?
S2 C10 C15 C14 177.3(5) . . . . ?

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
N2 H2 O3 0.66(6) 2.05(6) 2.692(8) 166(7) .
N1 H1B Br 0.90 2.31 3.178(5) 163.0 .
N1 H1A S2 0.90 2.78 3.670(6) 170.1 .
N1 H1A O3 0.90 2.29 3.087(7) 148.1 .
N1 H1A O1 0.90 2.24 3.043(7) 147.7 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.124