# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
J.Camp
D.Craig
A.White
_publ_contact_author_name        'Donald Craig'
_publ_contact_author_email       d.craig@imperial.ac.uk

data_3
_database_code_depnum_ccdc_archive 'CCDC 775144'
#TrackingRef 'D-Craig-cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N O4 S2, 0.10H2O'
_chemical_formula_sum            'C25 H25.20 N O4.10 S2'
_chemical_formula_weight         469.38

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1743(3)
_cell_length_b                   9.9834(4)
_cell_length_c                   13.0708(4)
_cell_angle_alpha                79.253(3)
_cell_angle_beta                 76.645(3)
_cell_angle_gamma                86.290(3)
_cell_volume                     1144.06(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4194
_cell_measurement_theta_min      3.0451
_cell_measurement_theta_max      28.9598

_exptl_crystal_description       'platy needles'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             494
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8098
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         29.02
_reflns_number_total             5098
_reflns_number_gt                3652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_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^)+(0.0577P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5098
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_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
N1 N 0.65944(15) 0.57258(15) 0.24154(10) 0.0230(3) Uani 1 1 d . . .
C2 C 0.51000(18) 0.54924(19) 0.31891(13) 0.0239(4) Uani 1 1 d . . .
H2A H 0.5082 0.4562 0.3636 0.029 Uiso 1 1 calc R . .
C3 C 0.40002(19) 0.55972(17) 0.24707(13) 0.0224(4) Uani 1 1 d . . .
C4 C 0.4821(2) 0.61138(17) 0.13870(13) 0.0235(4) Uani 1 1 d . . .
C5 C 0.4325(2) 0.65317(19) 0.04403(14) 0.0317(4) Uani 1 1 d . . .
H5A H 0.3287 0.6555 0.0445 0.038 Uiso 1 1 calc R . .
C6 C 0.5375(3) 0.6910(2) -0.05034(15) 0.0383(5) Uani 1 1 d . . .
H6A H 0.5052 0.7194 -0.1152 0.046 Uiso 1 1 calc R . .
C7 C 0.6875(3) 0.6881(2) -0.05154(15) 0.0374(5) Uani 1 1 d . . .
H7A H 0.7574 0.7133 -0.1175 0.045 Uiso 1 1 calc R . .
C8 C 0.7393(2) 0.64918(19) 0.04157(14) 0.0315(4) Uani 1 1 d . . .
H8A H 0.8431 0.6482 0.0407 0.038 Uiso 1 1 calc R . .
C9 C 0.6338(2) 0.61172(17) 0.13582(13) 0.0230(4) Uani 1 1 d . . .
S10 S 0.80504(5) 0.47832(5) 0.26498(4) 0.02667(13) Uani 1 1 d . . .
O11 O 0.93407(13) 0.54468(14) 0.19571(10) 0.0363(3) Uani 1 1 d . . .
O12 O 0.78922(14) 0.45650(14) 0.37843(10) 0.0331(3) Uani 1 1 d . . .
C13 C 0.78980(19) 0.32138(19) 0.22661(14) 0.0267(4) Uani 1 1 d . . .
C14 C 0.8658(2) 0.2996(2) 0.12640(15) 0.0359(5) Uani 1 1 d . . .
H14A H 0.9294 0.3673 0.0798 0.043 Uiso 1 1 calc R . .
C15 C 0.8482(2) 0.1787(2) 0.09483(17) 0.0422(5) Uani 1 1 d . . .
H15A H 0.9002 0.1641 0.0259 0.051 Uiso 1 1 calc R . .
C16 C 0.7565(2) 0.0779(2) 0.16103(17) 0.0395(5) Uani 1 1 d . . .
C17 C 0.6825(2) 0.1019(2) 0.26121(17) 0.0404(5) Uani 1 1 d . . .
H17A H 0.6194 0.0339 0.3079 0.048 Uiso 1 1 calc R . .
C18 C 0.6982(2) 0.2219(2) 0.29471(15) 0.0338(5) Uani 1 1 d . . .
H18A H 0.6468 0.2364 0.3638 0.041 Uiso 1 1 calc R . .
C19 C 0.7349(3) -0.0523(2) 0.1249(2) 0.0591(7) Uani 1 1 d . . .
H19A H 0.7210 -0.1273 0.1862 0.089 Uiso 1 1 calc R . .
H19B H 0.8233 -0.0717 0.0709 0.089 Uiso 1 1 calc R . .
H19C H 0.6462 -0.0427 0.0941 0.089 Uiso 1 1 calc R . .
C20 C 0.4835(2) 0.6578(2) 0.38951(14) 0.0322(4) Uani 1 1 d . . .
H20A H 0.5573 0.6453 0.4342 0.048 Uiso 1 1 calc R . .
H20B H 0.3823 0.6494 0.4352 0.048 Uiso 1 1 calc R . .
H20C H 0.4937 0.7484 0.3445 0.048 Uiso 1 1 calc R . .
C21 C 0.2565(2) 0.52574(18) 0.27489(14) 0.0274(4) Uani 1 1 d . . .
H21A H 0.2016 0.5440 0.2203 0.033 Uiso 1 1 calc R . .
C22 C 0.1735(2) 0.46171(18) 0.38348(14) 0.0281(4) Uani 1 1 d . . .
H22A H 0.0667 0.4912 0.3944 0.034 Uiso 1 1 calc R . .
H22B H 0.2160 0.4908 0.4387 0.034 Uiso 1 1 calc R . .
S23 S 0.18869(6) 0.27953(5) 0.39543(4) 0.03294(14) Uani 1 1 d . . .
O24 O 0.14357(18) 0.24295(15) 0.30762(11) 0.0484(4) Uani 1 1 d . . .
O25 O 0.33629(16) 0.23870(15) 0.41173(12) 0.0514(4) Uani 1 1 d . . .
C26 C 0.0567(2) 0.21592(18) 0.51176(14) 0.0285(4) Uani 1 1 d . . .
C27 C 0.0823(2) 0.2215(2) 0.61148(16) 0.0407(5) Uani 1 1 d . . .
H27A H 0.1710 0.2607 0.6174 0.049 Uiso 1 1 calc R . .
C28 C -0.0225(3) 0.1693(2) 0.70200(16) 0.0460(6) Uani 1 1 d . . .
H28A H -0.0066 0.1756 0.7702 0.055 Uiso 1 1 calc R . .
C29 C -0.1503(2) 0.10815(19) 0.69552(16) 0.0389(5) Uani 1 1 d . . .
C30 C -0.1739(2) 0.1035(2) 0.59600(16) 0.0378(5) Uani 1 1 d . . .
H30A H -0.2616 0.0623 0.5905 0.045 Uiso 1 1 calc R . .
C31 C -0.0724(2) 0.15765(19) 0.50378(15) 0.0316(4) Uani 1 1 d . . .
H31A H -0.0911 0.1549 0.4357 0.038 Uiso 1 1 calc R . .
C32 C -0.2627(3) 0.0496(2) 0.79552(18) 0.0624(8) Uani 1 1 d . . .
H32A H -0.2098 -0.0019 0.8479 0.094 Uiso 1 1 calc R . .
H32B H -0.3293 -0.0112 0.7778 0.094 Uiso 1 1 calc R . .
H32C H -0.3221 0.1240 0.8256 0.094 Uiso 1 1 calc R . .
O40 O 0.470(2) -0.042(2) 0.4810(17) 0.088(6) Uiso 0.10 1 d P A -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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0190(7) 0.0300(8) 0.0185(7) -0.0046(6) -0.0009(6) -0.0010(6)
C2 0.0192(9) 0.0303(10) 0.0196(8) -0.0015(7) -0.0011(7) -0.0021(7)
C3 0.0239(9) 0.0195(9) 0.0240(9) -0.0045(7) -0.0050(8) 0.0002(7)
C4 0.0290(10) 0.0201(9) 0.0218(8) -0.0048(7) -0.0052(8) -0.0014(7)
C5 0.0404(11) 0.0283(10) 0.0294(10) -0.0048(8) -0.0142(9) 0.0012(9)
C6 0.0623(15) 0.0314(11) 0.0210(9) -0.0026(8) -0.0107(10) 0.0006(10)
C7 0.0545(14) 0.0291(11) 0.0220(9) -0.0026(8) 0.0040(9) -0.0049(10)
C8 0.0357(11) 0.0295(10) 0.0247(9) -0.0060(8) 0.0048(8) -0.0054(8)
C9 0.0290(10) 0.0184(9) 0.0218(9) -0.0052(7) -0.0044(8) -0.0017(7)
S10 0.0200(2) 0.0341(3) 0.0288(2) -0.01113(19) -0.00664(19) -0.00063(18)
O11 0.0199(7) 0.0454(8) 0.0444(8) -0.0144(6) -0.0018(6) -0.0071(6)
O12 0.0330(7) 0.0431(8) 0.0286(7) -0.0118(6) -0.0145(6) 0.0038(6)
C13 0.0199(9) 0.0316(10) 0.0316(10) -0.0111(8) -0.0087(8) 0.0038(8)
C14 0.0293(10) 0.0383(12) 0.0377(11) -0.0122(9) 0.0011(9) 0.0014(9)
C15 0.0405(12) 0.0474(13) 0.0409(12) -0.0224(10) -0.0040(10) 0.0069(10)
C16 0.0402(12) 0.0339(12) 0.0510(13) -0.0157(10) -0.0186(11) 0.0065(10)
C17 0.0434(12) 0.0329(11) 0.0441(12) -0.0047(9) -0.0094(10) -0.0035(10)
C18 0.0335(11) 0.0367(11) 0.0315(10) -0.0073(8) -0.0073(9) 0.0009(9)
C19 0.0672(17) 0.0466(15) 0.0720(17) -0.0288(13) -0.0179(14) -0.0002(13)
C20 0.0267(10) 0.0469(12) 0.0251(9) -0.0157(8) -0.0024(8) -0.0018(9)
C21 0.0269(10) 0.0305(10) 0.0252(9) -0.0043(7) -0.0074(8) -0.0009(8)
C22 0.0233(9) 0.0310(10) 0.0292(10) -0.0050(8) -0.0038(8) -0.0029(8)
S23 0.0321(3) 0.0315(3) 0.0296(3) -0.0049(2) 0.0050(2) -0.0041(2)
O24 0.0697(11) 0.0393(8) 0.0297(7) -0.0087(6) 0.0093(7) -0.0208(8)
O25 0.0289(8) 0.0440(9) 0.0656(10) 0.0041(8) 0.0082(7) 0.0055(7)
C26 0.0273(10) 0.0266(10) 0.0271(9) -0.0013(7) 0.0004(8) -0.0009(8)
C27 0.0418(12) 0.0453(13) 0.0353(11) -0.0058(9) -0.0076(10) -0.0110(10)
C28 0.0634(15) 0.0468(13) 0.0238(10) -0.0019(9) -0.0050(10) -0.0018(12)
C29 0.0453(13) 0.0238(10) 0.0366(11) 0.0008(8) 0.0075(10) 0.0023(9)
C30 0.0290(11) 0.0321(11) 0.0465(12) -0.0045(9) 0.0015(9) -0.0017(9)
C31 0.0303(10) 0.0327(11) 0.0304(10) -0.0037(8) -0.0056(9) -0.0008(8)
C32 0.0747(18) 0.0439(14) 0.0465(14) 0.0029(11) 0.0234(13) -0.0035(13)

_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
N1 C9 1.433(2) . ?
N1 C2 1.507(2) . ?
N1 S10 1.6379(14) . ?
C2 C3 1.516(2) . ?
C2 C20 1.523(2) . ?
C3 C21 1.331(2) . ?
C3 C4 1.458(2) . ?
C4 C9 1.384(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.385(3) . ?
C6 C7 1.371(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.385(2) . ?
S10 O11 1.4292(13) . ?
S10 O12 1.4324(13) . ?
S10 C13 1.7548(19) . ?
C13 C14 1.383(2) . ?
C13 C18 1.385(3) . ?
C14 C15 1.376(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.385(3) . ?
C16 C19 1.502(3) . ?
C17 C18 1.377(3) . ?
C21 C22 1.493(2) . ?
C22 S23 1.7954(19) . ?
S23 O24 1.4203(16) . ?
S23 O25 1.4404(15) . ?
S23 C26 1.7521(18) . ?
C26 C31 1.387(3) . ?
C26 C27 1.388(3) . ?
C27 C28 1.380(3) . ?
C28 C29 1.382(3) . ?
C29 C30 1.377(3) . ?
C29 C32 1.512(3) . ?
C30 C31 1.384(3) . ?

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
C9 N1 C2 108.39(13) . . ?
C9 N1 S10 121.74(11) . . ?
C2 N1 S10 119.49(11) . . ?
N1 C2 C3 103.61(13) . . ?
N1 C2 C20 108.74(14) . . ?
C3 C2 C20 113.31(14) . . ?
C21 C3 C4 125.40(17) . . ?
C21 C3 C2 127.63(15) . . ?
C4 C3 C2 106.95(14) . . ?
C9 C4 C5 119.26(16) . . ?
C9 C4 C3 109.81(15) . . ?
C5 C4 C3 130.89(17) . . ?
C6 C5 C4 118.76(19) . . ?
C7 C6 C5 120.94(18) . . ?
C6 C7 C8 121.36(18) . . ?
C9 C8 C7 117.51(19) . . ?
C4 C9 C8 122.16(17) . . ?
C4 C9 N1 110.19(14) . . ?
C8 C9 N1 127.64(17) . . ?
O11 S10 O12 120.07(8) . . ?
O11 S10 N1 106.55(8) . . ?
O12 S10 N1 105.58(7) . . ?
O11 S10 C13 108.14(8) . . ?
O12 S10 C13 108.79(8) . . ?
N1 S10 C13 107.01(8) . . ?
C14 C13 C18 120.23(18) . . ?
C14 C13 S10 119.54(15) . . ?
C18 C13 S10 120.20(13) . . ?
C15 C14 C13 119.33(19) . . ?
C14 C15 C16 121.64(18) . . ?
C15 C16 C17 117.9(2) . . ?
C15 C16 C19 121.31(19) . . ?
C17 C16 C19 120.8(2) . . ?
C18 C17 C16 121.6(2) . . ?
C17 C18 C13 119.29(18) . . ?
C3 C21 C22 126.39(17) . . ?
C21 C22 S23 109.17(12) . . ?
O24 S23 O25 118.75(10) . . ?
O24 S23 C26 107.75(9) . . ?
O25 S23 C26 108.60(9) . . ?
O24 S23 C22 108.27(9) . . ?
O25 S23 C22 107.37(9) . . ?
C26 S23 C22 105.32(8) . . ?
C31 C26 C27 120.06(17) . . ?
C31 C26 S23 119.60(15) . . ?
C27 C26 S23 120.33(15) . . ?
C28 C27 C26 119.3(2) . . ?
C27 C28 C29 121.4(2) . . ?
C30 C29 C28 118.55(18) . . ?
C30 C29 C32 120.7(2) . . ?
C28 C29 C32 120.7(2) . . ?
C29 C30 C31 121.4(2) . . ?
C30 C31 C26 119.33(19) . . ?

_diffrn_measured_fraction_theta_max 0.836
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.047

#===END