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


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       M.W.P.Bebbington@hw.ac.uk
_publ_contact_author_name        'Magnus W. P. Bebbington'
loop_
_publ_author_name
M.Bebbington
M.Higginbotham

data_3875
_database_code_depnum_ccdc_archive 'CCDC 871548'
#TrackingRef '3875.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C11 H19 N O3 S'

_chemical_formula_weight         245.33

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   P2(1)/c

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   19.8419(15)

_cell_length_b                   5.3049(4)

_cell_length_c                   11.5941(9)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.646(4)

_cell_angle_gamma                90.00

_cell_volume                     1220.31(16)

_cell_formula_units_Z            4

_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    9945

_cell_measurement_theta_min      3.51

_cell_measurement_theta_max      31.92

_exptl_crystal_description       BLOCK

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.56

_exptl_crystal_size_mid          0.38

_exptl_crystal_size_min          0.24

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.335

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             528

_exptl_absorpt_coefficient_mu    0.258

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.8689

_exptl_absorpt_correction_T_max  0.9406

_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_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 ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            27110

_diffrn_reflns_av_R_equivalents  0.0325

_diffrn_reflns_av_sigmaI/netI    0.0250

_diffrn_reflns_limit_h_min       -29

_diffrn_reflns_limit_h_max       29

_diffrn_reflns_limit_k_min       -7

_diffrn_reflns_limit_k_max       7

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       17

_diffrn_reflns_theta_min         3.51

_diffrn_reflns_theta_max         32.06

_reflns_number_total             4215

_reflns_number_gt                3567

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'

_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^)+(0.0433P)^2^+0.4258P] 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_number_reflns         4215

_refine_ls_number_parameters     154

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0417

_refine_ls_R_factor_gt           0.0329

_refine_ls_wR_factor_ref         0.0890

_refine_ls_wR_factor_gt          0.0846

_refine_ls_goodness_of_fit_ref   1.049

_refine_ls_restrained_S_all      1.049

_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

S2 S 0.320635(12) 0.34640(4) 0.44768(2) 0.01261(7) Uani 1 1 d . . .
O1 O 0.25051(3) 0.43253(14) 0.39533(6) 0.01360(14) Uani 1 1 d . . .
O21 O 0.33369(4) 0.09257(14) 0.41062(6) 0.01763(15) Uani 1 1 d . . .
O22 O 0.31749(4) 0.40121(15) 0.56772(6) 0.01800(15) Uani 1 1 d . . .
N3 N 0.37619(4) 0.52882(17) 0.38835(7) 0.01372(16) Uani 1 1 d . . .
H3 H 0.3740(7) 0.675(3) 0.4155(12) 0.016 Uiso 1 1 d . . .
C4 C 0.37155(5) 0.53061(19) 0.25904(8) 0.01295(17) Uani 1 1 d . . .
H4 H 0.3812 0.3571 0.2298 0.016 Uiso 1 1 calc R . .
C5 C 0.30032(5) 0.60735(18) 0.21975(8) 0.01240(17) Uani 1 1 d . . .
H5A H 0.2910 0.7812 0.2463 0.015 Uiso 1 1 calc R . .
H5B H 0.2980 0.6067 0.1344 0.015 Uiso 1 1 calc R . .
C6 C 0.24655(5) 0.43079(19) 0.26653(8) 0.01216(17) Uani 1 1 d . . .
H6 H 0.2558 0.2560 0.2385 0.015 Uiso 1 1 calc R . .
C7 C 0.17380(5) 0.49904(19) 0.23626(8) 0.01328(17) Uani 1 1 d . . .
H7 H 0.1441 0.3811 0.2798 0.016 Uiso 1 1 calc R . .
C8 C 0.15377(5) 0.7685(2) 0.27021(9) 0.01705(19) Uani 1 1 d . . .
H8A H 0.1618 0.7931 0.3539 0.020 Uiso 1 1 calc R . .
H8B H 0.1820 0.8909 0.2281 0.020 Uiso 1 1 calc R . .
C9 C 0.07927(5) 0.8168(2) 0.24166(10) 0.0210(2) Uani 1 1 d . . .
H9A H 0.0509 0.7030 0.2883 0.025 Uiso 1 1 calc R . .
H9B H 0.0677 0.9927 0.2620 0.025 Uiso 1 1 calc R . .
C10 C 0.06440(6) 0.7727(2) 0.11335(10) 0.0218(2) Uani 1 1 d . . .
H10A H 0.0891 0.8986 0.0670 0.026 Uiso 1 1 calc R . .
H10B H 0.0156 0.7953 0.0981 0.026 Uiso 1 1 calc R . .
C11 C 0.08556(5) 0.5069(2) 0.07702(9) 0.0192(2) Uani 1 1 d . . .
H11A H 0.0785 0.4873 -0.0072 0.023 Uiso 1 1 calc R . .
H11B H 0.0569 0.3814 0.1164 0.023 Uiso 1 1 calc R . .
C12 C 0.15973(5) 0.4561(2) 0.10716(9) 0.01681(19) Uani 1 1 d . . .
H12A H 0.1887 0.5694 0.0614 0.020 Uiso 1 1 calc R . .
H12B H 0.1711 0.2801 0.0868 0.020 Uiso 1 1 calc R . .
C13 C 0.42387(5) 0.7082(2) 0.21350(9) 0.01658(19) Uani 1 1 d . . .
H13 H 0.4249 0.8757 0.2425 0.020 Uiso 1 1 calc R . .
C14 C 0.46860(6) 0.6434(3) 0.13513(10) 0.0244(2) Uani 1 1 d . . .
H14A H 0.4712(8) 0.476(3) 0.1074(13) 0.029 Uiso 1 1 d . . .
H14B H 0.5006(8) 0.763(3) 0.1032(13) 0.029 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

S2 0.01570(12) 0.01142(11) 0.01070(11) 0.00044(8) -0.00018(8) 0.00055(8)
O1 0.0133(3) 0.0166(3) 0.0109(3) 0.0015(2) 0.0008(2) 0.0005(3)
O21 0.0246(4) 0.0116(3) 0.0167(3) -0.0006(3) -0.0011(3) 0.0025(3)
O22 0.0244(4) 0.0185(4) 0.0111(3) -0.0004(3) -0.0004(3) 0.0003(3)
N3 0.0147(4) 0.0133(4) 0.0132(4) -0.0014(3) -0.0001(3) -0.0010(3)
C4 0.0125(4) 0.0139(4) 0.0125(4) 0.0003(3) 0.0006(3) 0.0000(3)
C5 0.0118(4) 0.0131(4) 0.0123(4) 0.0018(3) 0.0005(3) -0.0020(3)
C6 0.0135(4) 0.0127(4) 0.0103(4) 0.0001(3) 0.0001(3) -0.0009(3)
C7 0.0117(4) 0.0136(4) 0.0146(4) 0.0002(3) 0.0001(3) -0.0014(3)
C8 0.0135(4) 0.0168(4) 0.0207(5) -0.0041(4) -0.0029(3) 0.0013(4)
C9 0.0143(4) 0.0201(5) 0.0285(6) -0.0045(4) -0.0019(4) 0.0024(4)
C10 0.0165(5) 0.0201(5) 0.0288(6) 0.0011(4) -0.0073(4) -0.0005(4)
C11 0.0157(4) 0.0212(5) 0.0207(5) -0.0008(4) -0.0045(4) -0.0030(4)
C12 0.0142(4) 0.0197(5) 0.0165(4) -0.0020(4) -0.0013(3) -0.0017(4)
C13 0.0128(4) 0.0179(4) 0.0190(5) 0.0027(4) -0.0007(3) -0.0026(3)
C14 0.0174(5) 0.0334(6) 0.0224(5) 0.0024(5) 0.0040(4) -0.0027(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

S2 O22 1.4238(8) . ?
S2 O21 1.4379(8) . ?
S2 O1 1.5792(7) . ?
S2 N3 1.6254(9) . ?
O1 C6 1.4946(11) . ?
N3 C4 1.5011(12) . ?
N3 H3 0.838(15) . ?
C4 C13 1.5022(14) . ?
C4 C5 1.5350(13) . ?
C4 H4 1.0000 . ?
C5 C6 1.5240(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5253(13) . ?
C6 H6 1.0000 . ?
C7 C8 1.5362(14) . ?
C7 C12 1.5365(14) . ?
C7 H7 1.0000 . ?
C8 C9 1.5328(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5314(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5317(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5326(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3228(15) . ?
C13 H13 0.9500 . ?
C14 H14A 0.947(17) . ?
C14 H14B 0.973(16) . ?

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

O22 S2 O21 119.56(5) . . ?
O22 S2 O1 105.57(4) . . ?
O21 S2 O1 108.48(4) . . ?
O22 S2 N3 109.24(5) . . ?
O21 S2 N3 107.80(5) . . ?
O1 S2 N3 105.30(4) . . ?
C6 O1 S2 114.74(6) . . ?
C4 N3 S2 113.10(6) . . ?
C4 N3 H3 111.5(9) . . ?
S2 N3 H3 110.7(10) . . ?
N3 C4 C13 108.67(8) . . ?
N3 C4 C5 110.12(7) . . ?
C13 C4 C5 111.53(8) . . ?
N3 C4 H4 108.8 . . ?
C13 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
C6 C5 C4 112.17(8) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O1 C6 C5 108.82(7) . . ?
O1 C6 C7 105.51(7) . . ?
C5 C6 C7 115.90(8) . . ?
O1 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
C6 C7 C8 114.13(8) . . ?
C6 C7 C12 110.49(8) . . ?
C8 C7 C12 110.05(8) . . ?
C6 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
C12 C7 H7 107.3 . . ?
C9 C8 C7 110.61(8) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 111.04(9) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 110.95(9) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 111.38(9) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C7 111.07(8) . . ?
C11 C12 H12A 109.4 . . ?
C7 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C7 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C4 123.37(11) . . ?
C14 C13 H13 118.3 . . ?
C4 C13 H13 118.3 . . ?
C13 C14 H14A 121.1(9) . . ?
C13 C14 H14B 122.5(9) . . ?
H14A C14 H14B 116.4(13) . . ?

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

O22 S2 O1 C6 170.61(6) . . . . ?
O21 S2 O1 C6 -60.10(7) . . . . ?
N3 S2 O1 C6 55.09(7) . . . . ?
O22 S2 N3 C4 -166.05(7) . . . . ?
O21 S2 N3 C4 62.59(8) . . . . ?
O1 S2 N3 C4 -53.07(7) . . . . ?
S2 N3 C4 C13 178.83(7) . . . . ?
S2 N3 C4 C5 56.40(9) . . . . ?
N3 C4 C5 C6 -58.54(10) . . . . ?
C13 C4 C5 C6 -179.27(8) . . . . ?
S2 O1 C6 C5 -59.39(9) . . . . ?
S2 O1 C6 C7 175.62(6) . . . . ?
C4 C5 C6 O1 58.77(10) . . . . ?
C4 C5 C6 C7 177.42(8) . . . . ?
O1 C6 C7 C8 65.82(10) . . . . ?
C5 C6 C7 C8 -54.64(11) . . . . ?
O1 C6 C7 C12 -169.54(8) . . . . ?
C5 C6 C7 C12 70.00(11) . . . . ?
C6 C7 C8 C9 -177.47(9) . . . . ?
C12 C7 C8 C9 57.66(11) . . . . ?
C7 C8 C9 C10 -57.46(12) . . . . ?
C8 C9 C10 C11 55.82(12) . . . . ?
C9 C10 C11 C12 -54.98(12) . . . . ?
C10 C11 C12 C7 55.83(12) . . . . ?
C6 C7 C12 C11 176.18(8) . . . . ?
C8 C7 C12 C11 -56.89(11) . . . . ?
N3 C4 C13 C14 126.83(11) . . . . ?
C5 C4 C13 C14 -111.59(12) . . . . ?

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

N3 H3 O21 0.838(15) 2.356(15) 3.1188(12) 151.7(13) 1_565

_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.662

_refine_diff_density_min         -0.366

_refine_diff_density_rms         0.055