# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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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# 
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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.
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data_UJ1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O3 S'
_chemical_formula_weight         403.48

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                   8.3806(3)
_cell_length_b                   11.1445(4)
_cell_length_c                   13.0469(5)
_cell_angle_alpha                107.100(3)
_cell_angle_beta                 90.343(3)
_cell_angle_gamma                93.898(3)
_cell_volume                     1161.55(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    278(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.2

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8573
_exptl_absorpt_correction_T_max  0.9482
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      278(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19204
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.17
_reflns_number_total             5125
_reflns_number_gt                2939
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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^ > 2\s(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^)+(0.0574P)^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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5125
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
S1 S 1.01600(6) 0.80469(6) 0.30591(4) 0.0583(2) Uani 1 1 d . . .
O1 O 1.06696(16) 0.91962(14) 0.28477(13) 0.0744(5) Uani 1 1 d . . .
O2 O 1.12963(14) 0.73538(14) 0.34211(12) 0.0709(4) Uani 1 1 d . . .
O3 O 0.76757(17) 0.47196(14) 0.37134(12) 0.0706(4) Uani 1 1 d . . .
N1 N 0.88102(17) 0.83932(15) 0.40050(12) 0.0497(4) Uani 1 1 d . . .
C1 C 0.6721(3) 0.4564(3) -0.09002(19) 0.0929(8) Uani 1 1 d . . .
H1A H 0.7405 0.4481 -0.1501 0.139 Uiso 1 1 calc R . .
H1B H 0.5750 0.4911 -0.1032 0.139 Uiso 1 1 calc R . .
H1C H 0.6473 0.3752 -0.0803 0.139 Uiso 1 1 calc R . .
C2 C 0.7562(2) 0.5428(3) 0.00984(17) 0.0662(6) Uani 1 1 d . . .
C3 C 0.7600(3) 0.6718(3) 0.0313(2) 0.0779(7) Uani 1 1 d . . .
H3 H 0.7078 0.7053 -0.0160 0.093 Uiso 1 1 calc R . .
C4 C 0.8387(3) 0.7523(2) 0.12040(19) 0.0709(6) Uani 1 1 d . . .
H4 H 0.8385 0.8390 0.1335 0.085 Uiso 1 1 calc R . .
C5 C 0.9183(2) 0.7032(2) 0.19049(16) 0.0531(5) Uani 1 1 d . . .
C16 C 0.8220(2) 0.7374(2) 0.44341(16) 0.0557(5) Uani 1 1 d . . .
H6A H 0.8031 0.7722 0.5193 0.067 Uiso 1 1 calc R . .
H6B H 0.9037 0.6780 0.4360 0.067 Uiso 1 1 calc R . .
C17 C 0.6700(2) 0.66840(19) 0.38777(15) 0.0470(5) Uani 1 1 d . . .
C8 C 0.6504(2) 0.5308(2) 0.36773(15) 0.0535(5) Uani 1 1 d . . .
C9 C 0.4899(2) 0.46191(19) 0.33811(16) 0.0510(5) Uani 1 1 d . . .
C10 C 0.3494(2) 0.5085(2) 0.38266(16) 0.0561(5) Uani 1 1 d . . .
H10 H 0.3520 0.5875 0.4331 0.067 Uiso 1 1 calc R . .
C11 C 0.2052(3) 0.4387(2) 0.35296(18) 0.0612(6) Uani 1 1 d . . .
H11 H 0.1121 0.4715 0.3844 0.073 Uiso 1 1 calc R . .
C12 C 0.1957(3) 0.3223(2) 0.27836(19) 0.0652(6) Uani 1 1 d . . .
C13 C 0.0378(3) 0.2468(2) 0.2431(2) 0.0987(9) Uani 1 1 d . . .
H13A H 0.0435 0.1644 0.2515 0.148 Uiso 1 1 calc R . .
H13B H 0.0155 0.2394 0.1692 0.148 Uiso 1 1 calc R . .
H13C H -0.0459 0.2886 0.2863 0.148 Uiso 1 1 calc R . .
C7 C 0.8361(3) 0.4966(2) 0.08112(18) 0.0685(6) Uani 1 1 d . . .
H14 H 0.8359 0.4100 0.0684 0.082 Uiso 1 1 calc R . .
C6 C 0.9159(2) 0.5754(2) 0.17052(17) 0.0610(6) Uani 1 1 d . . .
H15 H 0.9684 0.5418 0.2176 0.073 Uiso 1 1 calc R . .
C24 C 0.7596(2) 0.92037(19) 0.38861(14) 0.0467(5) Uani 1 1 d . . .
C19 C 0.6018(2) 0.86721(19) 0.36525(15) 0.0469(5) Uani 1 1 d . . .
C20 C 0.4848(2) 0.9454(2) 0.35356(16) 0.0573(6) Uani 1 1 d . . .
H18 H 0.3796 0.9123 0.3374 0.069 Uiso 1 1 calc R . .
C21 C 0.5220(3) 1.0702(2) 0.36540(18) 0.0638(6) Uani 1 1 d . . .
H19 H 0.4424 1.1210 0.3572 0.077 Uiso 1 1 calc R . .
C22 C 0.6766(3) 1.1207(2) 0.38941(18) 0.0659(6) Uani 1 1 d . . .
H20 H 0.7012 1.2057 0.3977 0.079 Uiso 1 1 calc R . .
C23 C 0.7958(2) 1.0456(2) 0.40122(16) 0.0589(6) Uani 1 1 d . . .
H21 H 0.9003 1.0800 0.4177 0.071 Uiso 1 1 calc R . .
C18 C 0.5676(2) 0.73504(18) 0.35262(15) 0.0486(5) Uani 1 1 d . . .
H22 H 0.4719 0.6953 0.3192 0.058 Uiso 1 1 calc R . .
C14 C 0.3361(3) 0.2755(2) 0.23448(18) 0.0690(6) Uani 1 1 d . . .
H23 H 0.3326 0.1967 0.1836 0.083 Uiso 1 1 calc R . .
C15 C 0.4820(3) 0.3431(2) 0.26458(18) 0.0647(6) Uani 1 1 d . . .
H24 H 0.5754 0.3087 0.2352 0.078 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 0.0341(3) 0.0695(4) 0.0699(4) 0.0192(3) -0.0020(2) -0.0006(3)
O1 0.0505(8) 0.0735(11) 0.1007(12) 0.0312(9) 0.0099(8) -0.0110(8)
O2 0.0386(7) 0.0829(11) 0.0866(11) 0.0161(9) -0.0118(7) 0.0127(7)
O3 0.0590(9) 0.0693(10) 0.0896(11) 0.0305(9) 0.0015(8) 0.0155(8)
N1 0.0376(8) 0.0582(11) 0.0529(10) 0.0167(8) -0.0061(7) -0.0003(8)
C1 0.0714(16) 0.123(2) 0.0675(17) 0.0045(16) -0.0060(13) -0.0001(16)
C2 0.0480(12) 0.093(2) 0.0516(14) 0.0125(13) 0.0049(10) 0.0042(13)
C3 0.0752(16) 0.100(2) 0.0630(16) 0.0300(15) -0.0083(13) 0.0132(15)
C4 0.0683(14) 0.0771(17) 0.0707(16) 0.0272(14) -0.0052(13) 0.0051(13)
C5 0.0394(10) 0.0659(15) 0.0564(13) 0.0212(11) 0.0044(9) 0.0059(10)
C16 0.0463(11) 0.0699(14) 0.0549(13) 0.0247(11) -0.0058(10) 0.0034(10)
C17 0.0434(10) 0.0550(13) 0.0448(11) 0.0187(10) -0.0001(9) 0.0021(10)
C8 0.0525(12) 0.0630(15) 0.0499(12) 0.0232(11) 0.0034(10) 0.0087(11)
C9 0.0544(12) 0.0506(13) 0.0530(12) 0.0231(11) 0.0000(10) 0.0033(10)
C10 0.0607(13) 0.0538(13) 0.0560(13) 0.0202(10) 0.0051(11) 0.0000(11)
C11 0.0576(13) 0.0606(15) 0.0724(15) 0.0312(13) 0.0075(11) 0.0007(11)
C12 0.0678(15) 0.0550(15) 0.0791(16) 0.0327(13) -0.0098(13) -0.0074(12)
C13 0.0803(17) 0.0803(18) 0.134(2) 0.0370(18) -0.0186(17) -0.0259(15)
C7 0.0667(14) 0.0711(16) 0.0631(15) 0.0129(13) 0.0019(12) 0.0035(13)
C6 0.0560(13) 0.0736(17) 0.0555(13) 0.0213(12) -0.0026(10) 0.0090(12)
C24 0.0425(10) 0.0511(13) 0.0435(11) 0.0103(9) -0.0046(8) 0.0002(10)
C19 0.0395(10) 0.0525(13) 0.0490(11) 0.0161(10) -0.0019(9) -0.0002(9)
C20 0.0416(11) 0.0672(15) 0.0673(14) 0.0262(12) -0.0016(10) 0.0033(11)
C21 0.0567(13) 0.0574(15) 0.0839(16) 0.0294(13) 0.0060(12) 0.0125(12)
C22 0.0685(15) 0.0492(14) 0.0774(16) 0.0151(12) 0.0060(12) 0.0015(12)
C23 0.0529(12) 0.0550(14) 0.0623(14) 0.0101(11) -0.0053(10) -0.0078(11)
C18 0.0387(10) 0.0551(13) 0.0522(12) 0.0180(10) -0.0033(9) -0.0042(9)
C14 0.0871(18) 0.0467(14) 0.0712(16) 0.0160(12) -0.0089(14) -0.0015(13)
C15 0.0696(15) 0.0540(15) 0.0723(15) 0.0203(12) 0.0024(12) 0.0110(12)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.4261(15) . ?
S1 O2 1.4268(14) . ?
S1 N1 1.6576(16) . ?
S1 C5 1.753(2) . ?
O3 C8 1.225(2) . ?
N1 C24 1.442(2) . ?
N1 C16 1.466(2) . ?
C1 C2 1.510(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.378(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(3) . ?
C16 C17 1.506(3) . ?
C16 H6A 0.9700 . ?
C16 H6B 0.9700 . ?
C17 C18 1.334(2) . ?
C17 C8 1.476(3) . ?
C8 C9 1.492(3) . ?
C9 C10 1.381(3) . ?
C9 C15 1.385(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.378(3) . ?
C12 C13 1.512(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C7 C6 1.374(3) . ?
C7 H14 0.9300 . ?
C6 H15 0.9300 . ?
C24 C23 1.368(3) . ?
C24 C19 1.405(2) . ?
C19 C20 1.392(2) . ?
C19 C18 1.442(3) . ?
C20 C21 1.367(3) . ?
C20 H18 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H19 0.9300 . ?
C22 C23 1.382(3) . ?
C22 H20 0.9300 . ?
C23 H21 0.9300 . ?
C18 H22 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H23 0.9300 . ?
C15 H24 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 O2 119.87(9) . . ?
O1 S1 N1 106.73(9) . . ?
O2 S1 N1 106.05(9) . . ?
O1 S1 C5 108.68(10) . . ?
O2 S1 C5 107.71(10) . . ?
N1 S1 C5 107.16(8) . . ?
C24 N1 C16 113.88(14) . . ?
C24 N1 S1 117.40(12) . . ?
C16 N1 S1 116.74(13) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.4(2) . . ?
C7 C2 C1 121.7(2) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 S1 120.55(16) . . ?
C4 C5 S1 119.92(18) . . ?
N1 C16 C17 112.88(15) . . ?
N1 C16 H6A 109.0 . . ?
C17 C16 H6A 109.0 . . ?
N1 C16 H6B 109.0 . . ?
C17 C16 H6B 109.0 . . ?
H6A C16 H6B 107.8 . . ?
C18 C17 C8 124.36(18) . . ?
C18 C17 C16 117.32(18) . . ?
C8 C17 C16 118.11(17) . . ?
O3 C8 C17 119.83(18) . . ?
O3 C8 C9 119.70(19) . . ?
C17 C8 C9 120.40(18) . . ?
C10 C9 C15 118.22(19) . . ?
C10 C9 C8 123.54(19) . . ?
C15 C9 C8 118.21(19) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C14 117.8(2) . . ?
C11 C12 C13 122.0(2) . . ?
C14 C12 C13 120.2(2) . . ?
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 . . ?
C6 C7 C2 121.6(2) . . ?
C6 C7 H14 119.2 . . ?
C2 C7 H14 119.2 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 H15 119.9 . . ?
C7 C6 H15 119.9 . . ?
C23 C24 C19 120.78(18) . . ?
C23 C24 N1 121.32(17) . . ?
C19 C24 N1 117.90(17) . . ?
C20 C19 C24 117.88(18) . . ?
C20 C19 C18 122.68(17) . . ?
C24 C19 C18 119.43(17) . . ?
C21 C20 C19 121.00(18) . . ?
C21 C20 H18 119.5 . . ?
C19 C20 H18 119.5 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H19 119.9 . . ?
C22 C21 H19 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H20 119.9 . . ?
C23 C22 H20 119.9 . . ?
C24 C23 C22 119.87(18) . . ?
C24 C23 H21 120.1 . . ?
C22 C23 H21 120.1 . . ?
C17 C18 C19 121.61(17) . . ?
C17 C18 H22 119.2 . . ?
C19 C18 H22 119.2 . . ?
C12 C14 C15 121.3(2) . . ?
C12 C14 H23 119.3 . . ?
C15 C14 H23 119.3 . . ?
C14 C15 C9 120.4(2) . . ?
C14 C15 H24 119.8 . . ?
C9 C15 H24 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.17
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.036
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.037 0.000 0.000 202 50 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 961970'