# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
####################################################################### 

data_mo_111104lt_0m
_database_code_depnum_ccdc_archive 'CCDC 876013'
#TrackingRef 'mo_111104lt_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O3 S'
_chemical_formula_weight         327.39

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 n 1'
_symmetry_space_group_name_hall  'P -2yac'

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

_cell_length_a                   9.0128(18)
_cell_length_b                   9.1833(18)
_cell_length_c                   10.1798(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.846(4)
_cell_angle_gamma                90.00
_cell_volume                     787.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2892
_cell_measurement_theta_min      2.5974
_cell_measurement_theta_max      25.9097

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8213
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            6296
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         26.30
_reflns_number_total             2990
_reflns_number_gt                2774
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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^)+(0.0328P)^2^+0.0831P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_number_reflns         2990
_refine_ls_number_parameters     210
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
S1 S 0.33209(5) 1.13132(5) 0.30360(4) 0.01619(11) Uani 1 1 d . . .
O1 O 0.37412(14) 0.79336(13) 0.26618(13) 0.0157(3) Uani 1 1 d . . .
O2 O 0.24069(15) 1.25323(14) 0.31894(14) 0.0217(3) Uani 1 1 d . . .
O3 O 0.49917(15) 1.12500(14) 0.38178(14) 0.0205(3) Uani 1 1 d . . .
N1 N 0.25475(17) 0.98371(16) 0.35011(16) 0.0148(3) Uani 1 1 d . . .
C1 C 0.5738(2) 0.4274(2) 0.0066(2) 0.0242(5) Uani 1 1 d . . .
H1 H 0.6022 0.3758 -0.0618 0.029 Uiso 1 1 calc R . .
C2 C 0.6154(3) 0.3751(2) 0.1411(2) 0.0318(5) Uani 1 1 d . . .
H2 H 0.6718 0.2857 0.1648 0.038 Uiso 1 1 calc R . .
C3 C 0.5771(3) 0.4496(2) 0.2432(2) 0.0279(5) Uani 1 1 d . . .
H3 H 0.6078 0.4116 0.3359 0.033 Uiso 1 1 calc R . .
C4 C 0.4933(2) 0.5803(2) 0.2097(2) 0.0160(4) Uani 1 1 d . . .
C5 C 0.4514(2) 0.66191(19) 0.3151(2) 0.0150(4) Uani 1 1 d . . .
C6 C 0.3458(2) 0.85553(19) 0.37754(19) 0.0149(4) Uani 1 1 d . . .
C7 C 0.0836(2) 0.9659(2) 0.30707(19) 0.0160(4) Uani 1 1 d . . .
C8 C -0.0021(2) 1.0570(2) 0.36271(19) 0.0175(4) Uani 1 1 d . . .
H8 H 0.0494 1.1341 0.4244 0.021 Uiso 1 1 calc R . .
C9 C -0.1640(2) 1.0341(2) 0.32705(19) 0.0188(4) Uani 1 1 d . . .
H9 H -0.2240 1.0975 0.3628 0.023 Uiso 1 1 calc R . .
C10 C -0.2390(2) 0.9197(2) 0.2399(2) 0.0221(4) Uani 1 1 d . . .
H10 H -0.3492 0.9030 0.2181 0.026 Uiso 1 1 calc R . .
C11 C 0.3005(2) 1.1088(2) 0.1237(2) 0.0227(4) Uani 1 1 d . . .
H11A H 0.1892 1.0831 0.0729 0.034 Uiso 1 1 calc R . .
H11B H 0.3692 1.0309 0.1124 0.034 Uiso 1 1 calc R . .
H11C H 0.3254 1.1999 0.0859 0.034 Uiso 1 1 calc R . .
C12 C 0.0087(2) 0.8535(2) 0.2166(2) 0.0187(4) Uani 1 1 d . . .
H12 H 0.0675 0.7933 0.1769 0.022 Uiso 1 1 calc R . .
C13 C -0.1518(2) 0.8295(2) 0.1845(2) 0.0221(4) Uani 1 1 d . . .
H13 H -0.2027 0.7512 0.1244 0.027 Uiso 1 1 calc R . .
C14 C 0.4011(2) 0.77099(19) 0.4922(2) 0.0161(4) Uani 1 1 d . . .
H14 H 0.3964 0.7913 0.5821 0.019 Uiso 1 1 calc R . .
C15 C 0.4689(2) 0.64366(19) 0.4532(2) 0.0163(4) Uani 1 1 d . . .
C16 C 0.5390(2) 0.5180(2) 0.5493(2) 0.0234(4) Uani 1 1 d . . .
H16A H 0.4881 0.4273 0.5050 0.035 Uiso 1 1 calc R . .
H16B H 0.5216 0.5319 0.6382 0.035 Uiso 1 1 calc R . .
H16C H 0.6533 0.5126 0.5677 0.035 Uiso 1 1 calc R . .
C17 C 0.4493(2) 0.6313(2) 0.0728(2) 0.0218(4) Uani 1 1 d . . .
H17 H 0.3902 0.7191 0.0476 0.026 Uiso 1 1 calc R . .
C18 C 0.4898(2) 0.5565(2) -0.0278(2) 0.0243(4) Uani 1 1 d . . .
H18 H 0.4598 0.5940 -0.1207 0.029 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
S1 0.0163(2) 0.0144(2) 0.0190(2) -0.0007(2) 0.00771(17) 0.0003(2)
O1 0.0177(6) 0.0117(6) 0.0183(6) 0.0012(5) 0.0072(5) 0.0037(5)
O2 0.0245(8) 0.0147(7) 0.0299(8) 0.0017(6) 0.0143(6) 0.0020(5)
O3 0.0154(6) 0.0214(7) 0.0243(8) 0.0002(6) 0.0066(6) -0.0018(5)
N1 0.0110(7) 0.0133(8) 0.0202(8) -0.0006(6) 0.0058(6) 0.0012(6)
C1 0.0250(10) 0.0225(11) 0.0279(12) -0.0065(9) 0.0131(9) 0.0030(8)
C2 0.0409(13) 0.0211(11) 0.0372(13) 0.0015(10) 0.0185(11) 0.0165(9)
C3 0.0356(12) 0.0228(11) 0.0279(11) 0.0054(9) 0.0146(10) 0.0133(9)
C4 0.0127(8) 0.0134(9) 0.0225(10) -0.0021(7) 0.0072(7) -0.0018(7)
C5 0.0132(9) 0.0090(8) 0.0219(10) 0.0021(7) 0.0050(7) 0.0003(6)
C6 0.0145(9) 0.0125(9) 0.0181(10) -0.0018(7) 0.0064(7) 0.0006(7)
C7 0.0132(9) 0.0183(9) 0.0157(9) 0.0025(7) 0.0043(7) 0.0005(7)
C8 0.0209(9) 0.0170(9) 0.0148(9) 0.0001(7) 0.0066(8) 0.0021(8)
C9 0.0164(9) 0.0204(10) 0.0202(11) 0.0027(8) 0.0072(8) 0.0062(8)
C10 0.0144(9) 0.0293(11) 0.0206(10) 0.0043(9) 0.0039(8) 0.0010(8)
C11 0.0224(10) 0.0267(11) 0.0191(10) 0.0026(8) 0.0075(8) 0.0061(8)
C12 0.0197(9) 0.0176(10) 0.0180(9) -0.0022(8) 0.0057(8) 0.0017(7)
C13 0.0180(10) 0.0213(10) 0.0225(11) -0.0037(8) 0.0017(8) -0.0025(8)
C14 0.0136(9) 0.0180(9) 0.0171(9) -0.0025(8) 0.0060(7) -0.0026(7)
C15 0.0148(9) 0.0144(9) 0.0191(9) 0.0000(7) 0.0051(7) -0.0008(7)
C16 0.0320(11) 0.0170(10) 0.0213(9) 0.0043(8) 0.0097(8) 0.0035(9)
C17 0.0264(10) 0.0161(9) 0.0235(10) 0.0012(8) 0.0098(8) 0.0062(8)
C18 0.0302(11) 0.0258(12) 0.0176(10) -0.0003(8) 0.0095(9) 0.0036(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
S1 O2 1.4311(13) . ?
S1 O3 1.4322(14) . ?
S1 N1 1.6681(16) . ?
S1 C11 1.762(2) . ?
O1 C6 1.372(2) . ?
O1 C5 1.394(2) . ?
N1 C6 1.405(2) . ?
N1 C7 1.455(2) . ?
C1 C2 1.371(3) . ?
C1 C18 1.383(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C17 1.388(3) . ?
C4 C5 1.464(3) . ?
C5 C15 1.368(3) . ?
C6 C14 1.341(3) . ?
C7 C12 1.388(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C13 1.392(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.439(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.500(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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 O3 120.22(8) . . ?
O2 S1 N1 106.85(8) . . ?
O3 S1 N1 105.80(7) . . ?
O2 S1 C11 108.59(9) . . ?
O3 S1 C11 108.78(9) . . ?
N1 S1 C11 105.66(9) . . ?
C6 O1 C5 106.36(14) . . ?
C6 N1 C7 116.57(14) . . ?
C6 N1 S1 117.64(12) . . ?
C7 N1 S1 120.74(11) . . ?
C2 C1 C18 118.94(19) . . ?
C2 C1 H1 120.5 . . ?
C18 C1 H1 120.5 . . ?
C1 C2 C3 121.52(19) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C17 C4 C3 118.20(18) . . ?
C17 C4 C5 120.46(16) . . ?
C3 C4 C5 121.34(18) . . ?
C15 C5 O1 109.47(15) . . ?
C15 C5 C4 136.43(16) . . ?
O1 C5 C4 114.10(16) . . ?
C14 C6 O1 110.93(16) . . ?
C14 C6 N1 131.90(18) . . ?
O1 C6 N1 116.85(16) . . ?
C12 C7 C8 120.58(17) . . ?
C12 C7 N1 119.77(16) . . ?
C8 C7 N1 119.56(16) . . ?
C9 C8 C7 119.16(17) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.66(18) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C13 119.57(18) . . ?
C9 C10 H10 120.2 . . ?
C13 C10 H10 120.2 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 119.77(17) . . ?
C13 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C12 C13 C10 120.22(18) . . ?
C12 C13 H13 119.9 . . ?
C10 C13 H13 119.9 . . ?
C6 C14 C15 107.03(17) . . ?
C6 C14 H14 126.5 . . ?
C15 C14 H14 126.5 . . ?
C5 C15 C14 106.21(16) . . ?
C5 C15 C16 129.27(17) . . ?
C14 C15 C16 124.51(18) . . ?
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 . . ?
C18 C17 C4 121.27(18) . . ?
C18 C17 H17 119.4 . . ?
C4 C17 H17 119.4 . . ?
C1 C18 C17 120.12(19) . . ?
C1 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.038