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

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Xu, Ming-Hua'
_publ_contact_author_email       xumh@mail.shcnc.ac.cn

_publ_section_title              
;
Dramatic Lithium Chloride Effect on the Reaction Stereocontrol
in Zn-Mediated Asymmetric Cinnamylation: Highly Practical
Synthesis of Enantioenriched b-Aryl Homoallylic Amines
;
loop_
_publ_author_name
'Ming-Hua Xu'
'Min Liu'
'An Shen'
'Xing-Wen Sun'
'Fei Deng'
;
Guo-Qiang Lin
;

data_cd27402
_database_code_depnum_ccdc_archive 'CCDC 788747'
#TrackingRef 'X-ray of 3a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Br N O2 S'
_chemical_formula_weight         424.39

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                   6.7852(8)
_cell_length_b                   16.4229(18)
_cell_length_c                   19.812(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2207.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2079
_cell_measurement_theta_min      4.802
_cell_measurement_theta_max      34.649

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.094
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.76413
_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            13131
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_av_sigmaI/netI    0.1177
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4758
_reflns_number_gt                1707
_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^)+(0.0897P)^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   0.022(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4758
_refine_ls_number_parameters     236
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1446
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   0.750
_refine_ls_restrained_S_all      0.770
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.028

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 0.31432(17) 0.22904(6) -0.16194(4) 0.1254(6) Uani 1 1 d . . .
S1 S 0.7667(2) 0.57784(9) -0.04477(8) 0.0872(5) Uani 1 1 d . . .
O1 O 0.8587(6) 0.6578(3) -0.0319(2) 0.1052(13) Uani 1 1 d . . .
O2 O 0.2390(9) 0.6795(3) 0.0073(4) 0.1266(18) Uani 1 1 d D . .
N1 N 0.5651(7) 0.5646(3) -0.0026(2) 0.0711(12) Uani 1 1 d D . .
C1 C 0.5780(8) 0.5236(3) 0.0623(2) 0.0757(15) Uani 1 1 d . . .
H1 H 0.6848 0.4838 0.0583 0.091 Uiso 1 1 calc R . .
C2 C 0.3904(9) 0.4750(3) 0.0727(3) 0.0834(16) Uani 1 1 d . . .
H2 H 0.2785 0.5128 0.0718 0.100 Uiso 1 1 calc R . .
C3 C 0.3929(12) 0.4330(5) 0.1400(3) 0.128(3) Uani 1 1 d D . .
H3 H 0.5174 0.4134 0.1511 0.154 Uiso 1 1 calc R . .
C4 C 0.2758(17) 0.4188(7) 0.1821(6) 0.132(5) Uiso 1 1 d D . .
H4A H 0.1458 0.4354 0.1766 0.154 Uiso 1 1 calc R . .
H4B H 0.3131 0.3909 0.2209 0.154 Uiso 1 1 calc R . .
C5 C 0.6326(10) 0.5790(4) 0.1215(3) 0.0818(15) Uani 1 1 d . . .
C6 C 0.4972(14) 0.6318(5) 0.1474(4) 0.120(3) Uani 1 1 d . . .
H6 H 0.3706 0.6339 0.1295 0.137 Uiso 1 1 calc R . .
C7 C 0.548(2) 0.6816(7) 0.1996(5) 0.128(5) Uani 1 1 d . . .
H7 H 0.4574 0.7193 0.2155 0.143 Uiso 1 1 calc R . .
C8 C 0.723(2) 0.6776(6) 0.2281(5) 0.129(4) Uani 1 1 d . . .
H8 H 0.7516 0.7105 0.2650 0.141 Uiso 1 1 calc R . .
C9 C 0.8585(14) 0.6266(6) 0.2042(4) 0.138(3) Uani 1 1 d . . .
H9 H 0.9835 0.6249 0.2235 0.146 Uiso 1 1 calc R . .
C10 C 0.8121(11) 0.5758(4) 0.1502(4) 0.111(2) Uani 1 1 d . . .
H10 H 0.9058 0.5394 0.1339 0.134 Uiso 1 1 calc R . .
C11 C 0.3626(9) 0.4140(4) 0.0179(3) 0.0824(16) Uani 1 1 d . . .
C12 C 0.5017(11) 0.3533(4) 0.0055(3) 0.101(2) Uani 1 1 d . . .
H12 H 0.6111 0.3495 0.0336 0.122 Uiso 1 1 calc R . .
C13 C 0.4831(13) 0.2991(4) -0.0468(4) 0.112(2) Uani 1 1 d . . .
H13 H 0.5786 0.2592 -0.0532 0.135 Uiso 1 1 calc R . .
C14 C 0.3314(14) 0.3030(4) -0.0879(3) 0.102(2) Uani 1 1 d . . .
C15 C 0.1839(12) 0.3573(6) -0.0780(4) 0.123(3) Uani 1 1 d . . .
H15 H 0.0730 0.3575 -0.1056 0.138 Uiso 1 1 calc R . .
C16 C 0.2035(10) 0.4133(4) -0.0247(4) 0.1046(19) Uani 1 1 d . . .
H16 H 0.1042 0.4515 -0.0181 0.126 Uiso 1 1 calc R . .
C17 C 0.6717(12) 0.5853(4) -0.1310(3) 0.111(2) Uani 1 1 d . . .
C18 C 0.8570(14) 0.5901(6) -0.1752(4) 0.125(4) Uani 1 1 d . . .
H18A H 0.9405 0.5443 -0.1658 0.142 Uiso 1 1 calc R . .
H18B H 0.9268 0.6396 -0.1654 0.142 Uiso 1 1 calc R . .
H18C H 0.8198 0.5894 -0.2219 0.142 Uiso 1 1 calc R . .
C19 C 0.5460(14) 0.6618(5) -0.1382(4) 0.123(3) Uani 1 1 d . . .
H19A H 0.4953 0.6651 -0.1834 0.144 Uiso 1 1 calc R . .
H19B H 0.6252 0.7090 -0.1290 0.144 Uiso 1 1 calc R . .
H19C H 0.4383 0.6596 -0.1068 0.144 Uiso 1 1 calc R . .
C20 C 0.562(2) 0.5087(5) -0.1458(4) 0.123(5) Uani 1 1 d . . .
H20A H 0.5304 0.5066 -0.1930 0.145 Uiso 1 1 calc R . .
H20B H 0.4425 0.5075 -0.1199 0.145 Uiso 1 1 calc R . .
H20C H 0.6422 0.4627 -0.1341 0.145 Uiso 1 1 calc R . .
H1A H 0.489(5) 0.6013(18) -0.002(2) 0.070(13) Uiso 1 1 d D . .
H2A H 0.311(6) 0.711(2) -0.011(2) 0.078(17) Uiso 1 1 d D . .
H2B H 0.128(9) 0.687(10) -0.010(7) 0.090(19) 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
Br1 0.1806(11) 0.1688(9) 0.1066(6) -0.0256(6) 0.0109(7) -0.0841(7)
S1 0.0830(10) 0.0850(10) 0.0935(10) 0.0047(8) 0.0106(8) 0.0147(9)
O1 0.078(3) 0.101(3) 0.136(3) -0.004(2) -0.006(3) -0.012(2)
O2 0.083(3) 0.097(4) 0.200(6) -0.027(4) -0.027(4) 0.016(3)
N1 0.069(3) 0.069(3) 0.076(3) -0.001(2) -0.002(2) 0.018(3)
C1 0.078(4) 0.078(4) 0.072(4) -0.001(3) -0.001(3) 0.012(3)
C2 0.096(4) 0.081(4) 0.074(4) 0.014(3) 0.002(3) 0.003(3)
C3 0.115(6) 0.170(7) 0.100(5) -0.006(5) -0.002(4) -0.013(6)
C5 0.092(5) 0.078(4) 0.075(4) -0.005(3) 0.000(4) 0.012(4)
C6 0.173(8) 0.142(6) 0.104(6) -0.040(5) -0.032(5) 0.041(6)
C7 0.202(13) 0.151(8) 0.129(8) -0.038(7) -0.036(8) 0.071(9)
C8 0.202(15) 0.119(7) 0.096(6) -0.010(5) 0.002(9) -0.023(9)
C9 0.143(8) 0.168(9) 0.103(6) 0.007(6) -0.037(6) -0.032(7)
C10 0.103(5) 0.123(5) 0.108(5) -0.010(5) -0.009(4) -0.010(5)
C11 0.086(4) 0.077(4) 0.084(4) 0.025(3) -0.006(3) -0.001(4)
C12 0.112(5) 0.094(5) 0.099(5) 0.007(4) -0.039(4) 0.016(4)
C13 0.156(7) 0.090(5) 0.090(5) 0.017(4) -0.008(5) 0.013(4)
C14 0.115(6) 0.099(5) 0.092(5) 0.020(4) -0.027(5) -0.043(5)
C15 0.100(6) 0.165(8) 0.105(6) 0.015(6) -0.023(5) -0.036(6)
C16 0.091(5) 0.107(5) 0.116(5) 0.027(4) -0.007(4) -0.015(4)
C17 0.158(6) 0.093(5) 0.082(4) 0.011(3) -0.003(4) -0.029(5)
C18 0.171(10) 0.174(8) 0.130(7) 0.032(6) 0.089(7) 0.026(7)
C19 0.173(7) 0.168(8) 0.087(5) 0.026(5) -0.052(5) 0.001(7)
C20 0.210(16) 0.129(7) 0.090(5) -0.022(4) 0.002(8) -0.089(9)

_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 C14 1.908(7) . ?
S1 O1 1.476(4) . ?
S1 N1 1.617(5) . ?
S1 C17 1.831(6) . ?
O2 H2A 0.798(19) . ?
O2 H2B 0.84(2) . ?
N1 C1 1.455(6) . ?
N1 H1A 0.793(19) . ?
C1 C2 1.516(8) . ?
C1 C5 1.529(8) . ?
C1 H1 0.9800 . ?
C2 C11 1.490(8) . ?
C2 C3 1.502(8) . ?
C2 H2 0.9800 . ?
C3 C4 1.175(10) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9300 . ?
C4 H4B 0.9300 . ?
C5 C10 1.346(8) . ?
C5 C6 1.363(9) . ?
C6 C7 1.364(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.312(15) . ?
C7 H7 0.9300 . ?
C8 C9 1.332(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(10) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.371(8) . ?
C11 C12 1.394(9) . ?
C12 C13 1.372(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.314(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(10) . ?
C15 C16 1.407(10) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C20 1.491(10) . ?
C17 C19 1.525(10) . ?
C17 C18 1.534(10) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O1 S1 N1 112.8(2) . . ?
O1 S1 C17 104.5(3) . . ?
N1 S1 C17 101.1(3) . . ?
H1A O2 H2A 82(4) . . ?
H1A O2 H2B 140(10) . . ?
H2A O2 H2B 106(10) . . ?
C1 N1 S1 117.9(4) . . ?
C1 N1 H1A 113(3) . . ?
S1 N1 H1A 117(3) . . ?
N1 C1 C2 108.2(4) . . ?
N1 C1 C5 114.6(4) . . ?
C2 C1 C5 114.4(5) . . ?
N1 C1 H1 106.3 . . ?
C2 C1 H1 106.3 . . ?
C5 C1 H1 106.3 . . ?
C11 C2 C3 109.8(5) . . ?
C11 C2 C1 111.2(5) . . ?
C3 C2 C1 110.7(5) . . ?
C11 C2 H2 108.4 . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.4 . . ?
C4 C3 C2 135.5(10) . . ?
C4 C3 H3 112.2 . . ?
C2 C3 H3 112.2 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 H4B 120.0 . . ?
H4A C4 H4B 120.0 . . ?
C10 C5 C6 118.4(6) . . ?
C10 C5 C1 121.3(6) . . ?
C6 C5 C1 120.2(6) . . ?
C5 C6 C7 119.7(9) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.7(11) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.2(10) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.5(9) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.3 . . ?
C5 C10 C9 120.4(8) . . ?
C5 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C16 C11 C12 114.8(6) . . ?
C16 C11 C2 123.6(6) . . ?
C12 C11 C2 121.6(6) . . ?
C13 C12 C11 122.3(6) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C14 C13 C12 120.5(7) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.5(7) . . ?
C13 C14 Br1 119.5(8) . . ?
C15 C14 Br1 119.0(7) . . ?
C14 C15 C16 118.0(7) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C11 C16 C15 122.8(7) . . ?
C11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C20 C17 C19 113.4(8) . . ?
C20 C17 C18 109.9(7) . . ?
C19 C17 C18 111.3(6) . . ?
C20 C17 S1 107.6(5) . . ?
C19 C17 S1 109.8(5) . . ?
C18 C17 S1 104.3(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 S1 N1 C1 -93.7(4) . . . . ?
C17 S1 N1 C1 155.3(4) . . . . ?
S1 N1 C1 C2 -147.1(4) . . . . ?
S1 N1 C1 C5 84.0(5) . . . . ?
N1 C1 C2 C11 59.2(6) . . . . ?
C5 C1 C2 C11 -171.7(5) . . . . ?
N1 C1 C2 C3 -178.5(5) . . . . ?
C5 C1 C2 C3 -49.3(7) . . . . ?
C11 C2 C3 C4 -94.9(13) . . . . ?
C1 C2 C3 C4 142.0(12) . . . . ?
N1 C1 C5 C10 -107.2(6) . . . . ?
C2 C1 C5 C10 126.9(6) . . . . ?
N1 C1 C5 C6 74.4(8) . . . . ?
C2 C1 C5 C6 -51.5(8) . . . . ?
C10 C5 C6 C7 2.3(12) . . . . ?
C1 C5 C6 C7 -179.2(8) . . . . ?
C5 C6 C7 C8 -3.2(17) . . . . ?
C6 C7 C8 C9 3.0(19) . . . . ?
C7 C8 C9 C10 -2.0(16) . . . . ?
C6 C5 C10 C9 -1.3(11) . . . . ?
C1 C5 C10 C9 -179.7(6) . . . . ?
C8 C9 C10 C5 1.1(13) . . . . ?
C3 C2 C11 C16 117.7(6) . . . . ?
C1 C2 C11 C16 -119.5(6) . . . . ?
C3 C2 C11 C12 -63.6(7) . . . . ?
C1 C2 C11 C12 59.2(7) . . . . ?
C16 C11 C12 C13 2.0(9) . . . . ?
C2 C11 C12 C13 -176.8(6) . . . . ?
C11 C12 C13 C14 0.5(10) . . . . ?
C12 C13 C14 C15 -3.7(11) . . . . ?
C12 C13 C14 Br1 177.9(5) . . . . ?
C13 C14 C15 C16 4.0(10) . . . . ?
Br1 C14 C15 C16 -177.5(4) . . . . ?
C12 C11 C16 C15 -1.6(9) . . . . ?
C2 C11 C16 C15 177.2(5) . . . . ?
C14 C15 C16 C11 -1.3(10) . . . . ?
O1 S1 C17 C20 -175.5(6) . . . . ?
N1 S1 C17 C20 -58.2(7) . . . . ?
O1 S1 C17 C19 -51.6(6) . . . . ?
N1 S1 C17 C19 65.7(5) . . . . ?
O1 S1 C17 C18 67.7(6) . . . . ?
N1 S1 C17 C18 -174.9(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
N1 H1A O2 0.793(19) 2.14(2) 2.915(7) 167(4) .
O2 H2A O1 0.798(19) 2.34(4) 2.834(7) 121(4) 4_465
O2 H2B O1 0.84(2) 1.94(7) 2.718(7) 155(16) 1_455

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062