# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
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#  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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         195.27
_chemical_absolute_configuration rmad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.5317(5)
_cell_length_b                   8.8235(6)
_cell_length_c                   15.0974(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1003.31(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416

_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            10128
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_theta_min         5.81
_diffrn_reflns_theta_max         70.94
_diffrn_reflns_theta_full        70.94
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             1896
_reflns_number_gt                1868
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0670
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_number_reflns         1896
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+0.0897P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.153
_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   0.027(15)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.77827(4) 0.74055(4) 0.90347(2) 0.02360(12) Uani d . 1 . .
C C1 0.81524(19) 0.65838(16) 0.79683(9) 0.0239(3) Uani d . 1 . .
C C2 0.9736(2) 0.66908(18) 0.75025(10) 0.0280(3) Uani d . 1 . .
C C3 0.9844(2) 0.59363(18) 0.66919(10) 0.0311(3) Uani d . 1 . .
C C4 0.8392(2) 0.51224(17) 0.63748(11) 0.0313(3) Uani d . 1 . .
C C5 0.6818(2) 0.50472(16) 0.68460(10) 0.0272(3) Uani d . 1 . .
C C6 0.66975(19) 0.57953(16) 0.76597(9) 0.0242(3) Uani d . 1 . .
C C7 0.5128(2) 0.58324(16) 0.82720(9) 0.0244(3) Uani d . 1 . .
C C8 0.4480(2) 0.42511(17) 0.85594(11) 0.0277(3) Uani d . 1 . .
C C9 0.5965(2) 0.33034(18) 0.89580(12) 0.0326(3) Uani d . 1 . .
C C10 0.2905(2) 0.4380(2) 0.91863(12) 0.0359(4) Uani d . 1 . .
N N1 0.57200(16) 0.67972(14) 0.90045(9) 0.0278(3) Uani d . 1 . .
O O1 0.88826(14) 0.65237(13) 0.96730(7) 0.0307(3) Uani d . 1 . .
H H1 0.493(3) 0.718(2) 0.9374(14) 0.037(5) Uiso d . 1 . .
H H2 1.073(2) 0.722(2) 0.7739(11) 0.024(4) Uiso d . 1 . .
H H3 1.085(3) 0.599(2) 0.6362(13) 0.030(4) Uiso d . 1 . .
H H4 0.849(3) 0.465(2) 0.5821(14) 0.037(5) Uiso d . 1 . .
H H5 0.581(3) 0.448(2) 0.6591(13) 0.030(5) Uiso d . 1 . .
H H7 0.414(3) 0.634(2) 0.7950(13) 0.030(5) Uiso d . 1 . .
H H8 0.405(3) 0.376(2) 0.8039(14) 0.034(5) Uiso d . 1 . .
H H9A 0.647(3) 0.382(2) 0.9481(13) 0.037(5) Uiso d . 1 . .
H H9B 0.691(3) 0.312(2) 0.8507(14) 0.040(5) Uiso d . 1 . .
H H9C 0.553(3) 0.230(2) 0.9190(13) 0.034(5) Uiso d . 1 . .
H H10A 0.327(3) 0.486(2) 0.9747(15) 0.039(5) Uiso d . 1 . .
H H10B 0.243(3) 0.344(2) 0.9357(12) 0.032(5) Uiso d . 1 . .
H H10C 0.193(3) 0.490(2) 0.8918(14) 0.036(5) Uiso d . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.02264(19) 0.02253(18) 0.02564(18) -0.00276(13) 0.00037(11) -0.00481(14)
C1 0.0272(7) 0.0186(6) 0.0259(7) 0.0014(5) -0.0018(5) -0.0009(5)
C2 0.0274(7) 0.0257(7) 0.0310(7) -0.0015(6) 0.0003(6) -0.0019(6)
C3 0.0356(8) 0.0285(8) 0.0290(7) 0.0006(6) 0.0077(7) -0.0011(6)
C4 0.0455(9) 0.0245(7) 0.0239(7) 0.0012(6) 0.0011(6) -0.0013(6)
C5 0.0345(8) 0.0212(7) 0.0259(7) -0.0010(6) -0.0066(6) -0.0009(5)
C6 0.0274(7) 0.0193(6) 0.0259(7) 0.0017(5) -0.0039(5) 0.0018(5)
C7 0.0227(7) 0.0212(7) 0.0291(7) 0.0009(5) -0.0057(6) -0.0015(6)
C8 0.0300(8) 0.0228(7) 0.0304(7) -0.0036(6) -0.0028(6) -0.0016(6)
C9 0.0388(8) 0.0243(7) 0.0345(8) 0.0018(7) -0.0024(7) 0.0010(6)
C10 0.0321(8) 0.0316(8) 0.0439(9) -0.0048(7) 0.0048(7) 0.0017(7)
N1 0.0201(6) 0.0277(6) 0.0356(7) 0.0003(5) 0.0025(5) -0.0096(5)
O1 0.0270(5) 0.0373(6) 0.0278(5) 0.0002(5) -0.0034(4) -0.0047(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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4901(11) ?
S1 N1 . 1.6443(12) ?
S1 C1 . 1.7875(14) ?
C1 C6 . 1.379(2) ?
C1 C2 . 1.388(2) ?
C2 C3 . 1.396(2) ?
C2 H2 . 0.954(18) ?
C3 C4 . 1.393(2) ?
C3 H3 . 0.91(2) ?
C4 C5 . 1.384(2) ?
C4 H4 . 0.94(2) ?
C5 C6 . 1.397(2) ?
C5 H5 . 0.99(2) ?
C6 C7 . 1.501(2) ?
C7 N1 . 1.4652(19) ?
C7 C8 . 1.540(2) ?
C7 H7 . 1.00(2) ?
C8 C9 . 1.520(2) ?
C8 C10 . 1.522(2) ?
C8 H8 . 0.95(2) ?
C9 H9A . 0.99(2) ?
C9 H9B . 1.00(2) ?
C9 H9C . 1.01(2) ?
C10 H10A . 0.99(2) ?
C10 H10B . 0.94(2) ?
C10 H10C . 0.96(2) ?
N1 H1 . 0.88(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 N1 . . 111.88(7) ?
O1 S1 C1 . . 106.50(6) ?
N1 S1 C1 . . 89.42(7) ?
C6 C1 C2 . . 123.10(13) ?
C6 C1 S1 . . 112.65(11) ?
C2 C1 S1 . . 124.24(12) ?
C1 C2 C3 . . 117.52(15) ?
C1 C2 H2 . . 121.3(10) ?
C3 C2 H2 . . 121.1(10) ?
C4 C3 C2 . . 120.09(15) ?
C4 C3 H3 . . 119.7(12) ?
C2 C3 H3 . . 120.2(12) ?
C5 C4 C3 . . 121.36(14) ?
C5 C4 H4 . . 120.5(13) ?
C3 C4 H4 . . 118.1(13) ?
C4 C5 C6 . . 119.00(14) ?
C4 C5 H5 . . 118.9(11) ?
C6 C5 H5 . . 122.1(11) ?
C1 C6 C5 . . 118.92(14) ?
C1 C6 C7 . . 114.00(12) ?
C5 C6 C7 . . 127.07(13) ?
N1 C7 C6 . . 103.76(12) ?
N1 C7 C8 . . 114.20(12) ?
C6 C7 C8 . . 113.77(13) ?
N1 C7 H7 . . 109.5(11) ?
C6 C7 H7 . . 107.4(11) ?
C8 C7 H7 . . 107.9(11) ?
C9 C8 C10 . . 111.61(14) ?
C9 C8 C7 . . 112.14(12) ?
C10 C8 C7 . . 110.75(13) ?
C9 C8 H8 . . 109.2(12) ?
C10 C8 H8 . . 106.2(12) ?
C7 C8 H8 . . 106.6(12) ?
C8 C9 H9A . . 110.0(12) ?
C8 C9 H9B . . 110.1(12) ?
H9A C9 H9B . . 110.2(17) ?
C8 C9 H9C . . 112.4(11) ?
H9A C9 H9C . . 104.9(15) ?
H9B C9 H9C . . 109.2(16) ?
C8 C10 H10A . . 110.4(13) ?
C8 C10 H10B . . 113.5(12) ?
H10A C10 H10B . . 104.7(17) ?
C8 C10 H10C . . 111.8(12) ?
H10A C10 H10C . . 111.5(17) ?
H10B C10 H10C . . 104.6(18) ?
C7 N1 S1 . . 119.87(10) ?
C7 N1 H1 . . 119.8(14) ?
S1 N1 H1 . . 119.4(14) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C6 . . . . 108.96(11) ?
N1 S1 C1 C6 . . . . -3.73(11) ?
O1 S1 C1 C2 . . . . -69.74(14) ?
N1 S1 C1 C2 . . . . 177.56(14) ?
C6 C1 C2 C3 . . . . -1.1(2) ?
S1 C1 C2 C3 . . . . 177.49(11) ?
C1 C2 C3 C4 . . . . 0.4(2) ?
C2 C3 C4 C5 . . . . 0.4(2) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
C2 C1 C6 C5 . . . . 0.9(2) ?
S1 C1 C6 C5 . . . . -177.80(10) ?
C2 C1 C6 C7 . . . . -179.94(14) ?
S1 C1 C6 C7 . . . . 1.34(16) ?
C4 C5 C6 C1 . . . . -0.1(2) ?
C4 C5 C6 C7 . . . . -179.10(14) ?
C1 C6 C7 N1 . . . . 2.17(16) ?
C5 C6 C7 N1 . . . . -178.77(13) ?
C1 C6 C7 C8 . . . . -122.52(14) ?
C5 C6 C7 C8 . . . . 56.54(19) ?
N1 C7 C8 C9 . . . . -64.96(17) ?
C6 C7 C8 C9 . . . . 53.92(18) ?
N1 C7 C8 C10 . . . . 60.43(17) ?
C6 C7 C8 C10 . . . . 179.31(13) ?
C6 C7 N1 S1 . . . . -5.46(15) ?
C8 C7 N1 S1 . . . . 118.96(13) ?
O1 S1 N1 C7 . . . . -102.08(12) ?
C1 S1 N1 C7 . . . . 5.50(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 4_467 0.88(2) 2.00(2) 2.8454(17) 160.3(19) ?

_database_code_depnum_ccdc_archive 'CCDC 984456'
