# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005

data_global

_journal_coden_Cambridge     177


loop_
_publ_author_name
'J. Clayden' 
'Mark S. Betson' 
'Madeline Helliwell'
'David Mitjans' 
  
_publ_contact_author_name     	'J.Clayden'  
_publ_contact_author_address 
;
School of Chemistry 
University of Manchester 
Oxford Road 
MANCHESTER 
M13 9PL 
UNITED KINGDOM 
;
         
_publ_contact_author_email       'J.P.CLAYDEN@MAN.AC.UK'

_publ_requested_journal       
'Organic & Biomolecular Chemistry'


_publ_section_title		
;
Kinetic and thermodynamic stereocontrol in the
atroposelective formation of sulfoxides by oxidation of
2-sulfanyl-1-naphthamides
;

_publ_section_exptl_refinement   
;
The data were collected using the RAXIS in 120 x 3 degree
phi oscillations, of 7 minutes per exposure.  The structure was
solved by direct methods and non-H atoms were refined anisotropically
whilst H atoms were included in calculated positions. The
absolute configuration was determined by refining the
Flack parameter.
;

_publ_section_references         
;
ENTER OTHER REFERENCES

Molecular Structure Corporation. (1995). teXsan.
Single Crystal Structure Analysis Software. Version 1.7.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.

Altomare, A., Cascarano, M.,
Giacovazzo, C., Guagliardi, A. (1993).
J. Appl. Cryst., 26, 343.
;

data_s889
_database_code_depnum_ccdc_archive 'CCDC 187714'
#------------------------------------------------------------------------------
_audit_creation_date             19100-10-03
_audit_creation_method           'by teXsan v1.7'
_audit_update_record             
;
?
;
#------------------------------------------------------------------------------

_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N O2 S'
_chemical_formula_weight         379.50

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  ?

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

_cell_length_a                   10.712
_cell_length_b                   13.782
_cell_length_c                   14.260
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2105.2
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    'one image'
_cell_measurement_theta_min      5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_detector       'scintillation counter'
_diffrn_measurement_device       'Rigaku RAXIS'
_diffrn_measurement_method       '60 x 3 degree phi scans'

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            18990
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         26.36
_reflns_number_total             4202
_reflns_number_gt                4028
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_structure_solution    
;
SHELXS86 (Sheldrick, 1985)
;
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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 w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.1286P] 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       0.092(7)
_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   -0.04(6)
_refine_ls_number_reflns         4202
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16919(3) 0.75425(3) 0.17301(2) 0.05011(13) Uani 1 d . . .
O1 O 0.17693(11) 0.64639(8) 0.16624(10) 0.0683(3) Uani 1 d . . .
O2 O 0.25203(11) 0.99152(8) 0.16618(9) 0.0630(3) Uani 1 d . . .
N1 N 0.41975(11) 0.91591(8) 0.10007(8) 0.0480(3) Uani 1 d . . .
C1 C 0.26925(12) 0.79043(10) 0.26859(9) 0.0444(3) Uani 1 d . . .
C2 C 0.34660(12) 0.86925(9) 0.25786(9) 0.0427(3) Uani 1 d . . .
C3 C 0.42620(12) 0.89761(10) 0.33353(10) 0.0463(3) Uani 1 d . . .
C4 C 0.50755(14) 0.97861(11) 0.32809(12) 0.0560(3) Uani 1 d . . .
H4 H 0.5105 1.0155 0.2735 0.067 Uiso 1 calc R . .
C5 C 0.58204(17) 1.00286(13) 0.40307(15) 0.0694(5) Uani 1 d . . .
H5 H 0.6362 1.0553 0.3982 0.083 Uiso 1 calc R . .
C6 C 0.57733(19) 0.94955(17) 0.48665(14) 0.0766(5) Uani 1 d . . .
H6 H 0.6269 0.9678 0.5372 0.092 Uiso 1 calc R . .
C7 C 0.50034(16) 0.87102(16) 0.49428(12) 0.0692(5) Uani 1 d . . .
H7 H 0.4985 0.8358 0.5499 0.083 Uiso 1 calc R . .
C8 C 0.42313(13) 0.84263(11) 0.41822(10) 0.0519(3) Uani 1 d . . .
C9 C 0.34231(14) 0.76092(12) 0.42497(10) 0.0564(4) Uani 1 d . . .
H9 H 0.3406 0.7248 0.4800 0.068 Uiso 1 calc R . .
C10 C 0.26782(13) 0.73495(11) 0.35238(10) 0.0529(3) Uani 1 d . . .
H10 H 0.2160 0.6811 0.3575 0.064 Uiso 1 calc R . .
C11 C 0.33704(12) 0.93099(9) 0.16964(10) 0.0457(3) Uani 1 d . . .
C12 C 0.40659(16) 0.96862(13) 0.00921(10) 0.0584(4) Uani 1 d . . .
H12 H 0.4747 0.9464 -0.0313 0.070 Uiso 1 calc R . .
C13 C 0.2845(2) 0.94285(18) -0.04076(13) 0.0790(5) Uani 1 d . . .
H13A H 0.2795 0.8738 -0.0490 0.119 Uiso 1 calc R . .
H13B H 0.2822 0.9740 -0.1009 0.119 Uiso 1 calc R . .
H13C H 0.2150 0.9646 -0.0037 0.119 Uiso 1 calc R . .
C14 C 0.4226(3) 1.07684(15) 0.02104(16) 0.0936(7) Uani 1 d . . .
H14A H 0.3532 1.1025 0.0557 0.140 Uiso 1 calc R . .
H14B H 0.4260 1.1071 -0.0395 0.140 Uiso 1 calc R . .
H14C H 0.4986 1.0897 0.0544 0.140 Uiso 1 calc R . .
C15 C 0.51975(15) 0.84209(13) 0.10629(12) 0.0633(4) Uani 1 d . . .
H15 H 0.5209 0.8178 0.1709 0.076 Uiso 1 calc R . .
C16 C 0.4900(2) 0.75584(15) 0.04205(17) 0.0895(7) Uani 1 d . . .
H16A H 0.5507 0.7056 0.0516 0.134 Uiso 1 calc R . .
H16B H 0.4923 0.7766 -0.0222 0.134 Uiso 1 calc R . .
H16C H 0.4083 0.7314 0.0565 0.134 Uiso 1 calc R . .
C17 C 0.64828(15) 0.8852(2) 0.08601(15) 0.0872(7) Uani 1 d . . .
H17A H 0.6519 0.9060 0.0218 0.131 Uiso 1 calc R . .
H17B H 0.7112 0.8369 0.0969 0.131 Uiso 1 calc R . .
H17C H 0.6625 0.9397 0.1265 0.131 Uiso 1 calc R . .
C18 C 0.02188(13) 0.78034(10) 0.22887(9) 0.0477(3) Uani 1 d . . .
C19 C -0.05868(15) 0.70404(12) 0.24688(11) 0.0567(4) Uani 1 d . . .
H19 H -0.0359 0.6407 0.2323 0.068 Uiso 1 calc R . .
C20 C -0.17490(16) 0.72373(14) 0.28732(13) 0.0651(4) Uani 1 d . . .
H20 H -0.2301 0.6732 0.2996 0.078 Uiso 1 calc R . .
C21 C -0.20759(16) 0.81720(14) 0.30882(12) 0.0658(4) Uani 1 d . . .
H21 H -0.2845 0.8296 0.3367 0.079 Uiso 1 calc R . .
C22 C -0.12703(16) 0.89366(13) 0.28947(13) 0.0662(4) Uani 1 d . . .
H22 H -0.1505 0.9569 0.3039 0.079 Uiso 1 calc R . .
C23 C -0.01163(15) 0.87602(11) 0.24866(13) 0.0582(4) Uani 1 d . . .
H23 H 0.0423 0.9269 0.2348 0.070 Uiso 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
S1 0.05062(19) 0.0543(2) 0.04535(19) -0.00786(15) 0.00475(13) -0.00171(15)
O1 0.0693(7) 0.0558(6) 0.0797(8) -0.0220(6) 0.0085(7) 0.0016(5)
O2 0.0672(6) 0.0557(6) 0.0662(6) 0.0104(5) 0.0126(6) 0.0204(5)
N1 0.0462(6) 0.0538(6) 0.0440(6) 0.0074(5) 0.0064(5) 0.0035(5)
C1 0.0420(6) 0.0476(6) 0.0436(6) -0.0003(5) 0.0069(5) 0.0017(5)
C2 0.0406(6) 0.0445(6) 0.0429(6) 0.0004(5) 0.0078(5) 0.0041(5)
C3 0.0402(6) 0.0494(7) 0.0494(7) -0.0032(6) 0.0075(6) 0.0038(5)
C4 0.0505(8) 0.0531(7) 0.0644(9) -0.0055(7) 0.0072(7) -0.0034(6)
C5 0.0531(9) 0.0679(10) 0.0871(12) -0.0173(9) -0.0008(9) -0.0065(8)
C6 0.0625(10) 0.0956(15) 0.0719(11) -0.0136(10) -0.0142(9) -0.0044(10)
C7 0.0598(9) 0.0940(13) 0.0539(9) 0.0004(8) -0.0083(8) 0.0016(9)
C8 0.0440(6) 0.0653(9) 0.0463(7) 0.0022(6) 0.0023(6) 0.0063(6)
C9 0.0541(7) 0.0664(9) 0.0487(7) 0.0125(7) 0.0039(6) 0.0043(8)
C10 0.0507(7) 0.0539(8) 0.0542(7) 0.0101(6) 0.0076(6) -0.0030(6)
C11 0.0459(6) 0.0429(6) 0.0482(7) 0.0023(5) 0.0049(6) 0.0009(5)
C12 0.0616(9) 0.0679(10) 0.0458(7) 0.0141(7) 0.0059(7) 0.0002(7)
C13 0.0730(11) 0.1046(15) 0.0596(10) 0.0095(10) -0.0101(9) 0.0128(11)
C14 0.1312(19) 0.0692(12) 0.0804(12) 0.0286(11) 0.0121(14) -0.0189(13)
C15 0.0556(8) 0.0805(11) 0.0539(8) 0.0147(8) 0.0162(7) 0.0213(8)
C16 0.0914(14) 0.0678(11) 0.1093(16) -0.0017(12) 0.0432(13) 0.0164(11)
C17 0.0478(9) 0.149(2) 0.0645(10) 0.0071(12) 0.0070(8) 0.0098(11)
C18 0.0480(7) 0.0519(7) 0.0433(6) -0.0030(6) -0.0029(6) 0.0000(6)
C19 0.0578(8) 0.0558(8) 0.0567(8) 0.0009(7) 0.0026(7) -0.0027(7)
C20 0.0531(8) 0.0756(10) 0.0666(9) 0.0087(8) 0.0068(7) -0.0055(7)
C21 0.0488(8) 0.0843(11) 0.0644(10) 0.0017(8) 0.0036(7) 0.0089(8)
C22 0.0578(8) 0.0671(9) 0.0739(11) -0.0079(9) -0.0002(8) 0.0158(7)
C23 0.0536(8) 0.0533(8) 0.0676(10) -0.0055(7) -0.0003(7) 0.0003(6)

_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
S1 O1 1.4920(11) . ?
S1 C18 1.8039(14) . ?
S1 C1 1.8042(14) . ?
O2 C11 1.2360(17) . ?
N1 C11 1.3462(17) . ?
N1 C15 1.4800(19) . ?
N1 C12 1.4921(17) . ?
C1 C2 1.3748(18) . ?
C1 C10 1.4187(19) . ?
C2 C3 1.430(2) . ?
C2 C11 1.5222(19) . ?
C3 C4 1.4183(19) . ?
C3 C8 1.426(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.419(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.424(2) . ?
C9 C10 1.355(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 C14 1.511(3) . ?
C12 C13 1.532(3) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C17 1.527(2) . ?
C15 C16 1.534(3) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.384(2) . ?
C18 C23 1.396(2) . ?
C19 C20 1.399(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(2) . ?
C22 H22 0.9300 . ?
C23 H23 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
O1 S1 C18 106.00(7) . . ?
O1 S1 C1 106.93(7) . . ?
C18 S1 C1 97.53(6) . . ?
C11 N1 C15 122.57(11) . . ?
C11 N1 C12 120.17(12) . . ?
C15 N1 C12 117.07(11) . . ?
C2 C1 C10 121.74(13) . . ?
C2 C1 S1 119.49(10) . . ?
C10 C1 S1 118.75(10) . . ?
C1 C2 C3 119.44(12) . . ?
C1 C2 C11 119.54(12) . . ?
C3 C2 C11 120.74(11) . . ?
C4 C3 C8 118.60(14) . . ?
C4 C3 C2 122.70(13) . . ?
C8 C3 C2 118.70(12) . . ?
C5 C4 C3 120.35(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.86(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.36(17) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.65(17) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 121.39(14) . . ?
C7 C8 C3 119.17(14) . . ?
C9 C8 C3 119.44(13) . . ?
C10 C9 C8 121.02(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C1 119.65(13) . . ?
C9 C10 H10 120.2 . . ?
C1 C10 H10 120.2 . . ?
O2 C11 N1 124.04(13) . . ?
O2 C11 C2 117.38(12) . . ?
N1 C11 C2 118.58(11) . . ?
N1 C12 C14 111.90(14) . . ?
N1 C12 C13 111.83(14) . . ?
C14 C12 C13 112.19(18) . . ?
N1 C12 H12 106.8 . . ?
C14 C12 H12 106.8 . . ?
C13 C12 H12 106.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C17 111.97(15) . . ?
N1 C15 C16 110.26(15) . . ?
C17 C15 C16 112.06(16) . . ?
N1 C15 H15 107.4 . . ?
C17 C15 H15 107.4 . . ?
C16 C15 H15 107.4 . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 121.33(13) . . ?
C19 C18 S1 118.42(11) . . ?
C23 C18 S1 120.17(11) . . ?
C18 C19 C20 118.95(15) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 120.15(16) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.66(15) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.24(16) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 118.65(16) . . ?
C22 C23 H23 120.7 . . ?
C18 C23 H23 120.7 . . ?

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 C1 C2 136.43(10) . . . . ?
C18 S1 C1 C2 -114.25(11) . . . . ?
O1 S1 C1 C10 -42.14(12) . . . . ?
C18 S1 C1 C10 67.18(12) . . . . ?
C10 C1 C2 C3 -1.24(19) . . . . ?
S1 C1 C2 C3 -179.76(9) . . . . ?
C10 C1 C2 C11 -175.16(12) . . . . ?
S1 C1 C2 C11 6.32(16) . . . . ?
C1 C2 C3 C4 -179.35(12) . . . . ?
C11 C2 C3 C4 -5.51(19) . . . . ?
C1 C2 C3 C8 0.22(18) . . . . ?
C11 C2 C3 C8 174.07(11) . . . . ?
C8 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C4 C5 179.87(14) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 179.99(17) . . . . ?
C6 C7 C8 C3 -0.4(3) . . . . ?
C4 C3 C8 C7 0.5(2) . . . . ?
C2 C3 C8 C7 -179.05(13) . . . . ?
C4 C3 C8 C9 -179.83(13) . . . . ?
C2 C3 C8 C9 0.57(19) . . . . ?
C7 C8 C9 C10 179.23(15) . . . . ?
C3 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C1 -0.6(2) . . . . ?
C2 C1 C10 C9 1.4(2) . . . . ?
S1 C1 C10 C9 179.98(11) . . . . ?
C15 N1 C11 O2 -179.43(15) . . . . ?
C12 N1 C11 O2 -4.6(2) . . . . ?
C15 N1 C11 C2 -0.3(2) . . . . ?
C12 N1 C11 C2 174.53(12) . . . . ?
C1 C2 C11 O2 80.09(17) . . . . ?
C3 C2 C11 O2 -93.75(16) . . . . ?
C1 C2 C11 N1 -99.09(15) . . . . ?
C3 C2 C11 N1 87.07(16) . . . . ?
C11 N1 C12 C14 64.3(2) . . . . ?
C15 N1 C12 C14 -120.56(18) . . . . ?
C11 N1 C12 C13 -62.52(19) . . . . ?
C15 N1 C12 C13 112.59(17) . . . . ?
C11 N1 C15 C17 -127.11(16) . . . . ?
C12 N1 C15 C17 57.9(2) . . . . ?
C11 N1 C15 C16 107.39(16) . . . . ?
C12 N1 C15 C16 -67.59(18) . . . . ?
O1 S1 C18 C19 -5.59(14) . . . . ?
C1 S1 C18 C19 -115.67(12) . . . . ?
O1 S1 C18 C23 177.67(12) . . . . ?
C1 S1 C18 C23 67.58(13) . . . . ?
C23 C18 C19 C20 -1.2(2) . . . . ?
S1 C18 C19 C20 -177.89(12) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 1.1(3) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C18 -0.8(3) . . . . ?
C19 C18 C23 C22 1.7(2) . . . . ?
S1 C18 C23 C22 178.35(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.026