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


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#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_10r_a
_database_code_depnum_ccdc_archive 'CCDC 902761'
#TrackingRef '10R_A.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N2 O4 S'
_chemical_formula_weight         394.44

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/c '

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

_cell_length_a                   7.090(10)
_cell_length_b                   12.017(16)
_cell_length_c                   20.97(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.51(3)
_cell_angle_gamma                90.00
_cell_volume                     1783(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2331
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.31

_exptl_crystal_description       rod
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.007
_exptl_crystal_size_mid          0.0024
_exptl_crystal_size_min          0.0019
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.999
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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_reflns_number            17226
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_sigmaI/netI    0.0739
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4329
_reflns_number_gt                2496
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0811P)^2^+0.2126P] 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     SHELXL
_refine_ls_extinction_coef       0.0022(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4329
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1749
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.30415(10) 0.18518(6) 0.14891(3) 0.0392(2) Uani 1 1 d . . .
O1 O 0.2812(3) 0.05630(17) 0.49330(9) 0.0559(6) Uani 1 1 d . . .
O2 O 0.1414(4) 0.21449(18) 0.46381(9) 0.0630(7) Uani 1 1 d . . .
O3 O 0.2094(3) 0.45132(15) 0.32430(9) 0.0512(6) Uani 1 1 d . . .
O4 O 0.2865(4) -0.00674(16) 0.20031(9) 0.0580(6) Uani 1 1 d . . .
N1 N 0.1907(3) 0.26947(17) 0.34560(9) 0.0366(5) Uani 1 1 d . . .
H1 H 0.1574 0.2881 0.3829 0.044 Uiso 1 1 calc R . .
N2 N 0.2372(3) 0.12677(16) 0.27306(9) 0.0304(5) Uani 1 1 d . . .
C1 C 0.3010(5) 0.0963(3) 0.55860(13) 0.0624(10) Uani 1 1 d . . .
H1A H 0.3575 0.1689 0.5594 0.094 Uiso 1 1 calc R . .
H1B H 0.3798 0.0461 0.5839 0.094 Uiso 1 1 calc R . .
H1C H 0.1787 0.1003 0.5758 0.094 Uiso 1 1 calc R . .
C2 C 0.2021(4) 0.1247(2) 0.44960(12) 0.0408(7) Uani 1 1 d . . .
C3 C 0.2033(4) 0.0807(2) 0.38389(11) 0.0337(6) Uani 1 1 d . . .
C4 C 0.2083(4) 0.1587(2) 0.33536(11) 0.0310(6) Uani 1 1 d . . .
C5 C 0.2192(4) 0.3567(2) 0.30416(12) 0.0357(6) Uani 1 1 d . . .
C6 C 0.2540(4) 0.3216(2) 0.24020(12) 0.0333(6) Uani 1 1 d . . .
C7 C 0.2886(4) 0.3895(2) 0.18572(12) 0.0394(7) Uani 1 1 d . . .
C8 C 0.2990(5) 0.5148(2) 0.18679(15) 0.0575(9) Uani 1 1 d . . .
H8A H 0.2474 0.5406 0.2259 0.069 Uiso 1 1 calc R . .
H8B H 0.4311 0.5362 0.1885 0.069 Uiso 1 1 calc R . .
C9 C 0.1994(6) 0.5748(3) 0.13209(17) 0.0736(11) Uani 1 1 d . . .
H9A H 0.1988 0.6534 0.1426 0.088 Uiso 1 1 calc R . .
H9B H 0.0689 0.5501 0.1293 0.088 Uiso 1 1 calc R . .
C10 C 0.2731(6) 0.5635(3) 0.06713(15) 0.0668(10) Uani 1 1 d . . .
H10A H 0.4067 0.5816 0.0701 0.080 Uiso 1 1 calc R . .
H10B H 0.2099 0.6179 0.0392 0.080 Uiso 1 1 calc R . .
C11 C 0.2598(4) 0.2106(2) 0.22688(11) 0.0316(6) Uani 1 1 d . . .
C12 C 0.3179(4) 0.3262(2) 0.13371(12) 0.0423(7) Uani 1 1 d . . .
C13 C 0.2486(6) 0.4496(3) 0.03650(16) 0.0672(10) Uani 1 1 d . . .
H13A H 0.1173 0.4274 0.0377 0.081 Uiso 1 1 calc R . .
H13B H 0.2775 0.4550 -0.0080 0.081 Uiso 1 1 calc R . .
C14 C 0.3718(5) 0.3604(3) 0.06838(14) 0.0592(9) Uani 1 1 d . . .
H14A H 0.3678 0.2951 0.0411 0.071 Uiso 1 1 calc R . .
H14B H 0.5013 0.3868 0.0717 0.071 Uiso 1 1 calc R . .
C15 C 0.2571(4) 0.0139(2) 0.25551(12) 0.0386(7) Uani 1 1 d . . .
C16 C 0.2382(4) -0.0676(2) 0.30489(12) 0.0382(6) Uani 1 1 d . . .
C17 C 0.2457(5) -0.1795(2) 0.28710(15) 0.0537(8) Uani 1 1 d . . .
H17 H 0.2642 -0.1984 0.2449 0.064 Uiso 1 1 calc R . .
C18 C 0.2260(5) -0.2610(2) 0.33136(17) 0.0609(9) Uani 1 1 d . . .
H18 H 0.2334 -0.3355 0.3198 0.073 Uiso 1 1 calc R . .
C19 C 0.1951(5) -0.2321(3) 0.39320(16) 0.0594(9) Uani 1 1 d . . .
H19 H 0.1773 -0.2880 0.4229 0.071 Uiso 1 1 calc R . .
C20 C 0.1899(4) -0.1231(2) 0.41235(14) 0.0474(8) Uani 1 1 d . . .
H20 H 0.1711 -0.1064 0.4548 0.057 Uiso 1 1 calc R . .
C21 C 0.2127(4) -0.0360(2) 0.36836(12) 0.0354(6) Uani 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
S1 0.0510(5) 0.0367(4) 0.0303(3) 0.0007(3) 0.0046(3) 0.0026(3)
O1 0.0796(17) 0.0542(13) 0.0335(10) 0.0033(9) -0.0004(10) 0.0106(11)
O2 0.103(2) 0.0506(13) 0.0355(11) -0.0044(10) 0.0079(11) 0.0178(13)
O3 0.0756(16) 0.0302(11) 0.0489(12) -0.0043(9) 0.0124(10) 0.0038(10)
O4 0.103(2) 0.0368(11) 0.0348(11) -0.0042(9) 0.0138(11) 0.0048(11)
N1 0.0494(15) 0.0297(11) 0.0314(11) -0.0023(9) 0.0084(10) 0.0024(10)
N2 0.0331(13) 0.0287(11) 0.0293(10) 0.0004(8) 0.0009(8) 0.0013(9)
C1 0.081(3) 0.076(2) 0.0298(15) 0.0011(15) -0.0016(15) 0.0056(19)
C2 0.0504(19) 0.0400(16) 0.0328(14) 0.0032(11) 0.0081(12) -0.0024(13)
C3 0.0380(16) 0.0329(14) 0.0303(13) 0.0012(10) 0.0034(10) 0.0008(11)
C4 0.0321(15) 0.0309(13) 0.0300(12) -0.0031(10) 0.0021(10) 0.0003(10)
C5 0.0395(17) 0.0298(13) 0.0380(14) 0.0018(11) 0.0048(11) 0.0013(11)
C6 0.0343(15) 0.0305(13) 0.0351(13) 0.0021(11) 0.0028(10) 0.0014(11)
C7 0.0444(18) 0.0370(15) 0.0366(14) 0.0063(11) 0.0016(12) -0.0018(12)
C8 0.090(3) 0.0358(16) 0.0468(18) 0.0035(13) 0.0049(16) -0.0003(16)
C9 0.104(3) 0.0426(19) 0.076(2) 0.0133(17) 0.014(2) 0.0106(19)
C10 0.094(3) 0.052(2) 0.055(2) 0.0202(16) 0.0055(18) 0.0018(19)
C11 0.0295(15) 0.0328(13) 0.0321(13) 0.0006(10) -0.0002(10) 0.0003(10)
C12 0.0503(19) 0.0406(16) 0.0362(14) 0.0090(12) 0.0031(12) 0.0007(13)
C13 0.094(3) 0.060(2) 0.0466(18) 0.0150(16) -0.0040(18) 0.0016(19)
C14 0.084(3) 0.056(2) 0.0386(16) 0.0096(14) 0.0105(16) 0.0049(18)
C15 0.0503(19) 0.0304(14) 0.0353(14) -0.0029(11) 0.0029(12) 0.0011(12)
C16 0.0463(18) 0.0296(13) 0.0388(14) 0.0015(11) 0.0039(12) 0.0007(12)
C17 0.077(2) 0.0335(16) 0.0512(17) -0.0022(14) 0.0085(15) 0.0003(15)
C18 0.086(3) 0.0275(15) 0.069(2) 0.0031(14) 0.0078(18) -0.0027(15)
C19 0.077(3) 0.0376(17) 0.063(2) 0.0128(15) 0.0020(18) -0.0082(16)
C20 0.058(2) 0.0403(17) 0.0435(15) 0.0086(13) 0.0040(14) -0.0102(14)
C21 0.0343(16) 0.0338(14) 0.0382(14) 0.0029(11) 0.0030(11) -0.0013(11)

_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 C11 1.712(3) . ?
S1 C12 1.729(4) . ?
O1 C2 1.329(3) . ?
O1 C1 1.450(4) . ?
O2 C2 1.206(4) . ?
O3 C5 1.216(3) . ?
O4 C15 1.214(3) . ?
N1 C4 1.356(4) . ?
N1 C5 1.385(3) . ?
N1 H1 0.8600 . ?
N2 C4 1.389(4) . ?
N2 C11 1.414(3) . ?
N2 C15 1.415(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.477(4) . ?
C3 C4 1.385(4) . ?
C3 C21 1.442(4) . ?
C5 C6 1.442(4) . ?
C6 C11 1.364(4) . ?
C6 C7 1.437(4) . ?
C7 C12 1.356(4) . ?
C7 C8 1.508(4) . ?
C8 C9 1.495(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.495(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.517(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C14 1.502(4) . ?
C13 C14 1.513(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.438(4) . ?
C16 C17 1.397(4) . ?
C16 C21 1.406(4) . ?
C17 C18 1.362(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.411(4) . ?
C20 H20 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
C11 S1 C12 90.96(13) . . ?
C2 O1 C1 117.3(3) . . ?
C4 N1 C5 128.8(2) . . ?
C4 N1 H1 115.6 . . ?
C5 N1 H1 115.6 . . ?
C4 N2 C11 118.5(2) . . ?
C4 N2 C15 122.1(2) . . ?
C11 N2 C15 119.2(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 121.6(3) . . ?
O2 C2 C3 125.0(2) . . ?
O1 C2 C3 113.3(3) . . ?
C4 C3 C21 119.2(2) . . ?
C4 C3 C2 116.5(2) . . ?
C21 C3 C2 124.2(2) . . ?
N1 C4 C3 122.8(2) . . ?
N1 C4 N2 116.1(2) . . ?
C3 C4 N2 121.1(2) . . ?
O3 C5 N1 118.4(3) . . ?
O3 C5 C6 127.8(2) . . ?
N1 C5 C6 113.7(2) . . ?
C11 C6 C7 112.5(2) . . ?
C11 C6 C5 119.0(2) . . ?
C7 C6 C5 128.4(2) . . ?
C12 C7 C6 111.3(3) . . ?
C12 C7 C8 124.2(3) . . ?
C6 C7 C8 124.4(3) . . ?
C9 C8 C7 116.7(3) . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C7 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 H9A 107.6 . . ?
C10 C9 H9A 107.6 . . ?
C8 C9 H9B 107.6 . . ?
C10 C9 H9B 107.6 . . ?
H9A C9 H9B 107.1 . . ?
C9 C10 C13 115.5(3) . . ?
C9 C10 H10A 108.4 . . ?
C13 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C13 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C6 C11 N2 123.4(2) . . ?
C6 C11 S1 112.33(19) . . ?
N2 C11 S1 124.2(2) . . ?
C7 C12 C14 129.9(3) . . ?
C7 C12 S1 112.8(2) . . ?
C14 C12 S1 117.1(2) . . ?
C14 C13 C10 113.8(3) . . ?
C14 C13 H13A 108.8 . . ?
C10 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C10 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C12 C14 C13 115.1(3) . . ?
C12 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
C12 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O4 C15 N2 118.0(2) . . ?
O4 C15 C16 125.2(3) . . ?
N2 C15 C16 116.8(2) . . ?
C17 C16 C21 121.4(2) . . ?
C17 C16 C15 117.1(3) . . ?
C21 C16 C15 121.4(2) . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 121.8(3) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 116.4(3) . . ?
C16 C21 C3 119.1(2) . . ?
C20 C21 C3 124.4(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.089