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

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#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 N2 O6 S'
_chemical_formula_weight         406.45

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                   8.4767(8)
_cell_length_b                   8.8960(8)
_cell_length_c                   15.3032(14)
_cell_angle_alpha                75.243(5)
_cell_angle_beta                 84.666(5)
_cell_angle_gamma                65.095(5)
_cell_volume                     1012.02(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3250
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11312
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3340
_reflns_number_gt                2361
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0992P)²+0.1322P] where P=(Fo²+2Fc²)/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         3340
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1451
_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
C1 C 0.2497(4) 0.7816(3) 0.48309(18) 0.0453(7) Uani 1 1 d . . .
C2 C 0.2571(3) 0.9309(3) 0.50620(18) 0.0457(7) Uani 1 1 d . . .
C3 C 0.3096(4) 0.9448(4) 0.5843(2) 0.0611(8) Uani 1 1 d . . .
H3 H 0.3488 0.8526 0.6342 0.073 Uiso 1 1 calc R . .
C4 C 0.3016(5) 1.1048(5) 0.5857(3) 0.0736(10) Uani 1 1 d . . .
H4 H 0.3372 1.1193 0.6375 0.088 Uiso 1 1 calc R . .
C5 C 0.2419(5) 1.2408(5) 0.5117(3) 0.0695(10) Uani 1 1 d . . .
H5 H 0.2387 1.3454 0.5143 0.083 Uiso 1 1 calc R . .
C6 C 0.1869(4) 1.2251(4) 0.4338(2) 0.0605(8) Uani 1 1 d . . .
H6 H 0.1453 1.3175 0.3842 0.073 Uiso 1 1 calc R . .
C7 C 0.1958(3) 1.0678(3) 0.43214(18) 0.0449(7) Uani 1 1 d . . .
C8 C 0.1507(4) 1.0100(3) 0.35985(19) 0.0468(7) Uani 1 1 d . . .
C9 C 0.1578(4) 0.7299(4) 0.34667(19) 0.0489(7) Uani 1 1 d . . .
H9A H 0.0908 0.8012 0.2919 0.059 Uiso 1 1 calc R . .
H9B H 0.0902 0.6731 0.3836 0.059 Uiso 1 1 calc R . .
C10 C 0.3266(3) 0.5960(3) 0.32151(18) 0.0431(7) Uani 1 1 d . . .
H10A H 0.3005 0.5151 0.3002 0.052 Uiso 1 1 calc R . .
H10B H 0.3999 0.5341 0.3752 0.052 Uiso 1 1 calc R . .
C11 C 0.5897(6) 0.4414(5) 0.1459(2) 0.0848(12) Uani 1 1 d . . .
H11A H 0.5210 0.5326 0.0965 0.102 Uiso 1 1 calc R . .
H11B H 0.7045 0.3830 0.1232 0.102 Uiso 1 1 calc R . .
C12 C 0.5093(4) 0.3221(4) 0.1755(2) 0.0603(8) Uani 1 1 d . . .
C13 C 0.4415(6) 0.2311(6) 0.1985(3) 0.0874(13) Uani 1 1 d . . .
C14 C 0.7756(4) 0.4695(4) 0.2540(2) 0.0628(9) Uani 1 1 d . . .
H14A H 0.8463 0.3504 0.2548 0.075 Uiso 1 1 calc R . .
H14B H 0.7626 0.4797 0.3162 0.075 Uiso 1 1 calc R . .
C15 C 0.8722(4) 0.5730(4) 0.2040(2) 0.0491(7) Uani 1 1 d . . .
C16 C 0.8745(5) 0.7692(4) 0.0590(2) 0.0656(9) Uani 1 1 d . . .
C17 C 0.7666(8) 0.8201(6) -0.0245(3) 0.127(2) Uani 1 1 d . . .
H17A H 0.7929 0.7216 -0.0476 0.191 Uiso 1 1 calc R . .
H17B H 0.7923 0.9038 -0.0693 0.191 Uiso 1 1 calc R . .
H17C H 0.6455 0.8674 -0.0100 0.191 Uiso 1 1 calc R . .
C18 C 1.0656(6) 0.6820(6) 0.0409(3) 0.1041(15) Uani 1 1 d . . .
H18A H 1.1316 0.6542 0.0949 0.156 Uiso 1 1 calc R . .
H18B H 1.0988 0.7570 -0.0063 0.156 Uiso 1 1 calc R . .
H18C H 1.0881 0.5794 0.0227 0.156 Uiso 1 1 calc R . .
C19 C 0.8318(7) 0.9172(5) 0.1017(3) 0.1116(16) Uani 1 1 d . . .
H19A H 0.7137 0.9547 0.1218 0.167 Uiso 1 1 calc R . .
H19B H 0.8459 1.0094 0.0580 0.167 Uiso 1 1 calc R . .
H19C H 0.9087 0.8815 0.1524 0.167 Uiso 1 1 calc R . .
N1 N 0.1844(3) 0.8378(3) 0.39566(14) 0.0429(6) Uani 1 1 d . . .
N2 N 0.6061(3) 0.5158(3) 0.21770(19) 0.0637(8) Uani 1 1 d . . .
O1 O 0.2922(3) 0.6362(3) 0.52810(14) 0.0669(7) Uani 1 1 d . . .
O2 O 0.0938(3) 1.0879(3) 0.28457(15) 0.0688(7) Uani 1 1 d . . .
O3 O 0.5108(3) 0.7736(3) 0.27558(16) 0.0688(7) Uani 1 1 d . . .
O4 O 0.3357(3) 0.7664(3) 0.15881(15) 0.0790(7) Uani 1 1 d . . .
O5 O 0.9868(4) 0.5814(3) 0.23973(17) 0.0799(7) Uani 1 1 d . . .
O6 O 0.8162(2) 0.6444(2) 0.11945(13) 0.0504(5) Uani 1 1 d . . .
S1 S 0.44296(10) 0.68248(9) 0.23736(5) 0.0492(3) Uani 1 1 d . . .
H13 H 0.411(6) 0.135(7) 0.220(3) 0.133(18) Uiso 1 1 d . . .


_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
C1 O1 1.215(3) . ?
C1 N1 1.382(3) . ?
C1 C2 1.485(4) . ?
C2 C3 1.366(4) . ?
C2 C7 1.383(4) . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.473(4) . ?
C8 O2 1.206(3) . ?
C8 N1 1.401(3) . ?
C9 N1 1.454(3) . ?
C9 C10 1.520(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 S1 1.766(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.451(5) . ?
C11 N2 1.463(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.149(5) . ?
C13 H13 0.96(5) . ?
C14 N2 1.441(4) . ?
C14 C15 1.505(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O5 1.195(4) . ?
C15 O6 1.321(3) . ?
C16 O6 1.479(3) . ?
C16 C17 1.499(5) . ?
C16 C18 1.507(5) . ?
C16 C19 1.511(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 S1 1.620(2) . ?
O3 S1 1.424(2) . ?
O4 S1 1.415(2) . ?

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 C1 N1 124.1(3) . . ?
O1 C1 C2 129.7(3) . . ?
N1 C1 C2 106.2(2) . . ?
C3 C2 C7 122.1(3) . . ?
C3 C2 C1 130.1(3) . . ?
C7 C2 C1 107.8(2) . . ?
C2 C3 C4 116.8(3) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 117.7(3) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C2 121.0(3) . . ?
C6 C7 C8 130.6(3) . . ?
C2 C7 C8 108.4(2) . . ?
O2 C8 N1 124.0(3) . . ?
O2 C8 C7 130.0(3) . . ?
N1 C8 C7 106.0(2) . . ?
N1 C9 C10 113.3(2) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 S1 113.46(19) . . ?
C9 C10 H10A 108.9 . . ?
S1 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
S1 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 N2 113.2(3) . . ?
C12 C11 H11A 108.9 . . ?
N2 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N2 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 178.2(4) . . ?
C12 C13 H13 167(3) . . ?
N2 C14 C15 115.6(2) . . ?
N2 C14 H14A 108.4 . . ?
C15 C14 H14A 108.4 . . ?
N2 C14 H14B 108.4 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
O5 C15 O6 127.2(3) . . ?
O5 C15 C14 121.3(3) . . ?
O6 C15 C14 111.5(3) . . ?
O6 C16 C17 101.7(3) . . ?
O6 C16 C18 109.5(3) . . ?
C17 C16 C18 111.3(4) . . ?
O6 C16 C19 108.8(3) . . ?
C17 C16 C19 112.0(4) . . ?
C18 C16 C19 112.9(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C8 111.6(2) . . ?
C1 N1 C9 124.0(2) . . ?
C8 N1 C9 124.5(2) . . ?
C14 N2 C11 119.7(3) . . ?
C14 N2 S1 119.4(2) . . ?
C11 N2 S1 119.0(3) . . ?
C15 O6 C16 122.3(2) . . ?
O4 S1 O3 119.79(15) . . ?
O4 S1 N2 108.63(16) . . ?
O3 S1 N2 107.50(14) . . ?
O4 S1 C10 107.67(14) . . ?
O3 S1 C10 108.40(13) . . ?
N2 S1 C10 103.70(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
O1 C1 C2 C3 -1.6(5) . . . . ?
N1 C1 C2 C3 179.2(3) . . . . ?
O1 C1 C2 C7 179.4(3) . . . . ?
N1 C1 C2 C7 0.2(3) . . . . ?
C7 C2 C3 C4 -1.1(5) . . . . ?
C1 C2 C3 C4 180.0(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C7 -0.8(5) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C5 C6 C7 C8 -178.8(3) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C1 C2 C7 C6 179.9(3) . . . . ?
C3 C2 C7 C8 180.0(3) . . . . ?
C1 C2 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 O2 -0.5(5) . . . . ?
C2 C7 C8 O2 -179.7(3) . . . . ?
C6 C7 C8 N1 -179.6(3) . . . . ?
C2 C7 C8 N1 1.3(3) . . . . ?
N1 C9 C10 S1 -69.9(3) . . . . ?
N2 C11 C12 C13 88(12) . . . . ?
N2 C14 C15 O5 158.6(3) . . . . ?
N2 C14 C15 O6 -23.0(4) . . . . ?
O1 C1 N1 C8 -178.6(3) . . . . ?
C2 C1 N1 C8 0.7(3) . . . . ?
O1 C1 N1 C9 0.2(4) . . . . ?
C2 C1 N1 C9 179.4(2) . . . . ?
O2 C8 N1 C1 179.7(3) . . . . ?
C7 C8 N1 C1 -1.2(3) . . . . ?
O2 C8 N1 C9 0.9(4) . . . . ?
C7 C8 N1 C9 -180.0(2) . . . . ?
C10 C9 N1 C1 -69.5(3) . . . . ?
C10 C9 N1 C8 109.1(3) . . . . ?
C15 C14 N2 C11 86.5(3) . . . . ?
C15 C14 N2 S1 -77.9(3) . . . . ?
C12 C11 N2 C14 110.3(3) . . . . ?
C12 C11 N2 S1 -85.2(4) . . . . ?
O5 C15 O6 C16 -9.2(4) . . . . ?
C14 C15 O6 C16 172.5(2) . . . . ?
C17 C16 O6 C15 -176.0(3) . . . . ?
C18 C16 O6 C15 66.2(4) . . . . ?
C19 C16 O6 C15 -57.7(4) . . . . ?
C14 N2 S1 O4 142.1(2) . . . . ?
C11 N2 S1 O4 -22.5(3) . . . . ?
C14 N2 S1 O3 11.1(3) . . . . ?
C11 N2 S1 O3 -153.5(2) . . . . ?
C14 N2 S1 C10 -103.6(2) . . . . ?
C11 N2 S1 C10 91.8(3) . . . . ?
C9 C10 S1 O4 -60.8(2) . . . . ?
C9 C10 S1 O3 70.2(2) . . . . ?
C9 C10 S1 N2 -175.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.937
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.059
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.937       
RESPONSE: The data collection strategy was kept for 100 percent
completion. The apparent incompleteness could be due to
blind regions in reciprocal space.
;


_database_code_depnum_ccdc_archive 'CCDC 968919'
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#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N2 O6 S'
_chemical_formula_weight         420.47

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   Cc

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

_cell_length_a                   19.9851(13)
_cell_length_b                   13.9008(8)
_cell_length_c                   8.3536(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.968(3)
_cell_angle_gamma                90.00
_cell_volume                     2120.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2670
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      23.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6294
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2887
_reflns_number_gt                2590
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0304P)²+0.6112P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_number_reflns         2887
_refine_ls_number_parameters     270
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.81520(14) 0.90756(19) 0.9402(3) 0.0485(6) Uani 1 1 d . . .
C2 C 0.86149(14) 0.98976(17) 1.0360(3) 0.0434(6) Uani 1 1 d . . .
C3 C 0.92468(15) 0.9934(2) 1.1886(4) 0.0556(7) Uani 1 1 d . . .
H3 H 0.9447 0.9379 1.2522 0.067 Uiso 1 1 calc R . .
C4 C 0.95711(16) 1.0819(2) 1.2433(4) 0.0656(8) Uani 1 1 d . . .
H4 H 0.9993 1.0861 1.3463 0.079 Uiso 1 1 calc R . .
C5 C 0.92827(18) 1.1640(2) 1.1483(4) 0.0705(9) Uani 1 1 d . . .
H5 H 0.9515 1.2227 1.1875 0.085 Uiso 1 1 calc R . .
C6 C 0.86545(18) 1.16063(19) 0.9960(4) 0.0664(9) Uani 1 1 d . . .
H6 H 0.8460 1.2161 0.9315 0.080 Uiso 1 1 calc R . .
C7 C 0.83247(14) 1.07299(17) 0.9425(3) 0.0464(6) Uani 1 1 d . . .
C8 C 0.76568(15) 1.04623(19) 0.7874(4) 0.0512(7) Uani 1 1 d . . .
C9 C 0.70045(15) 0.8926(2) 0.6645(3) 0.0556(7) Uani 1 1 d . . .
H9A H 0.7149 0.8256 0.6704 0.067 Uiso 1 1 calc R . .
H9B H 0.6918 0.9164 0.5486 0.067 Uiso 1 1 calc R . .
C10 C 0.63030(14) 0.89958(18) 0.6921(3) 0.0442(6) Uani 1 1 d . . .
H10A H 0.6185 0.9666 0.7002 0.053 Uiso 1 1 calc R . .
H10B H 0.6365 0.8679 0.8007 0.053 Uiso 1 1 calc R . .
C11 C 0.47398(17) 0.7805(2) 0.6668(4) 0.0684(9) Uani 1 1 d . . .
H11A H 0.4897 0.7176 0.6452 0.082 Uiso 1 1 calc R . .
H11B H 0.4221 0.7763 0.6406 0.082 Uiso 1 1 calc R . .
C12 C 0.51345(17) 0.80336(19) 0.8527(4) 0.0575(7) Uani 1 1 d . . .
C13 C 0.5444(3) 0.8214(2) 0.9997(6) 0.0801(11) Uani 1 1 d . . .
C14 C 0.44370(14) 0.94133(18) 0.5205(3) 0.0481(6) Uani 1 1 d . . .
H14A H 0.4683 0.9902 0.4813 0.058 Uiso 1 1 calc R . .
H14B H 0.4437 0.9622 0.6313 0.058 Uiso 1 1 calc R . .
C15 C 0.36572(14) 0.93081(17) 0.3873(4) 0.0524(7) Uani 1 1 d . . .
H15A H 0.3659 0.9068 0.2784 0.063 Uiso 1 1 calc R . .
H15B H 0.3406 0.8840 0.4293 0.063 Uiso 1 1 calc R . .
C16 C 0.32488(16) 1.0242(2) 0.3532(4) 0.0564(7) Uani 1 1 d . . .
C17 C 0.20094(15) 1.09266(19) 0.2111(4) 0.0547(7) Uani 1 1 d . . .
C18 C 0.20527(18) 1.1495(2) 0.3689(4) 0.0716(9) Uani 1 1 d . . .
H18A H 0.1647 1.1933 0.3352 0.107 Uiso 1 1 calc R . .
H18B H 0.2503 1.1852 0.4151 0.107 Uiso 1 1 calc R . .
H18C H 0.2036 1.1063 0.4569 0.107 Uiso 1 1 calc R . .
C19 C 0.12756(18) 1.0418(2) 0.1275(5) 0.0771(10) Uani 1 1 d . . .
H19A H 0.1267 1.0028 0.0318 0.116 Uiso 1 1 calc R . .
H19B H 0.0891 1.0887 0.0848 0.116 Uiso 1 1 calc R . .
H19C H 0.1206 1.0018 0.2131 0.116 Uiso 1 1 calc R . .
C20 C 0.21608(19) 1.1537(2) 0.0785(4) 0.0745(10) Uani 1 1 d . . .
H20A H 0.2122 1.1145 -0.0195 0.112 Uiso 1 1 calc R . .
H20B H 0.2646 1.1802 0.1324 0.112 Uiso 1 1 calc R . .
H20C H 0.1810 1.2051 0.0388 0.112 Uiso 1 1 calc R . .
N1 N 0.75935(11) 0.94716(15) 0.7944(3) 0.0464(5) Uani 1 1 d . . .
N2 N 0.48406(11) 0.84955(14) 0.5462(2) 0.0460(5) Uani 1 1 d . . .
O1 O 0.82254(11) 0.82297(13) 0.9746(3) 0.0729(6) Uani 1 1 d . . .
O2 O 0.72322(12) 1.09579(14) 0.6712(3) 0.0785(7) Uani 1 1 d . . .
O3 O 0.57681(11) 0.74568(15) 0.5149(3) 0.0880(8) Uani 1 1 d . . .
O4 O 0.54643(12) 0.90053(18) 0.3619(2) 0.0819(7) Uani 1 1 d . . .
O5 O 0.35402(12) 1.10047(15) 0.3962(4) 0.1019(9) Uani 1 1 d . . .
O6 O 0.25342(9) 1.01052(11) 0.2668(2) 0.0523(5) Uani 1 1 d . . .
S1 S 0.55815(4) 0.84400(5) 0.51376(7) 0.0527(2) Uani 1 1 d . . .
H13 H 0.572(3) 0.839(3) 1.122(6) 0.130(16) Uiso 1 1 d . . .


_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
C1 O1 1.205(3) . ?
C1 N1 1.388(3) . ?
C1 C2 1.483(3) . ?
C2 C3 1.384(3) . ?
C2 C7 1.384(3) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.481(4) . ?
C8 O2 1.212(3) . ?
C8 N1 1.386(3) . ?
C9 N1 1.450(3) . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 S1 1.775(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.463(3) . ?
C11 C12 1.463(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.156(5) . ?
C13 H13 0.98(4) . ?
C14 N2 1.478(3) . ?
C14 C15 1.510(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.497(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O5 1.193(3) . ?
C16 O6 1.326(3) . ?
C17 O6 1.491(3) . ?
C17 C18 1.509(4) . ?
C17 C19 1.518(4) . ?
C17 C20 1.521(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N2 S1 1.612(2) . ?
O3 S1 1.416(2) . ?
O4 S1 1.428(2) . ?

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 C1 N1 124.9(2) . . ?
O1 C1 C2 129.3(2) . . ?
N1 C1 C2 105.7(2) . . ?
C3 C2 C7 120.4(2) . . ?
C3 C2 C1 131.4(2) . . ?
C7 C2 C1 108.2(2) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 117.9(3) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 121.5(2) . . ?
C6 C7 C8 130.7(2) . . ?
C2 C7 C8 107.8(2) . . ?
O2 C8 N1 123.5(2) . . ?
O2 C8 C7 130.3(2) . . ?
N1 C8 C7 106.1(2) . . ?
N1 C9 C10 111.9(2) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 S1 109.34(17) . . ?
C9 C10 H10A 109.8 . . ?
S1 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
S1 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
N2 C11 C12 115.0(2) . . ?
N2 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
N2 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 179.7(4) . . ?
C12 C13 H13 177(3) . . ?
N2 C14 C15 111.25(19) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 112.1(2) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O5 C16 O6 125.2(3) . . ?
O5 C16 C15 123.5(3) . . ?
O6 C16 C15 111.3(2) . . ?
O6 C17 C18 110.2(2) . . ?
O6 C17 C19 102.3(2) . . ?
C18 C17 C19 110.3(3) . . ?
O6 C17 C20 109.4(2) . . ?
C18 C17 C20 112.7(2) . . ?
C19 C17 C20 111.5(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 C1 112.1(2) . . ?
C8 N1 C9 123.3(2) . . ?
C1 N1 C9 124.6(2) . . ?
C11 N2 C14 116.6(2) . . ?
C11 N2 S1 118.49(18) . . ?
C14 N2 S1 120.09(17) . . ?
C16 O6 C17 121.7(2) . . ?
O3 S1 O4 119.00(16) . . ?
O3 S1 N2 107.61(13) . . ?
O4 S1 N2 107.02(12) . . ?
O3 S1 C10 107.01(13) . . ?
O4 S1 C10 106.86(13) . . ?
N2 S1 C10 109.06(11) . . ?

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
O1 C1 C2 C3 -0.2(5) . . . . ?
N1 C1 C2 C3 -179.3(3) . . . . ?
O1 C1 C2 C7 177.9(3) . . . . ?
N1 C1 C2 C7 -1.2(3) . . . . ?
C7 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C4 178.0(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C2 -1.0(4) . . . . ?
C5 C6 C7 C8 -179.9(3) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
C1 C2 C7 C6 -177.5(3) . . . . ?
C3 C2 C7 C8 180.0(2) . . . . ?
C1 C2 C7 C8 1.6(3) . . . . ?
C6 C7 C8 O2 -1.3(5) . . . . ?
C2 C7 C8 O2 179.7(3) . . . . ?
C6 C7 C8 N1 177.6(3) . . . . ?
C2 C7 C8 N1 -1.4(3) . . . . ?
N1 C9 C10 S1 172.76(18) . . . . ?
N2 C11 C12 C13 128(100) . . . . ?
N2 C14 C15 C16 -177.4(2) . . . . ?
C14 C15 C16 O5 14.9(4) . . . . ?
C14 C15 C16 O6 -166.4(2) . . . . ?
O2 C8 N1 C1 179.6(3) . . . . ?
C7 C8 N1 C1 0.7(3) . . . . ?
O2 C8 N1 C9 -1.0(4) . . . . ?
C7 C8 N1 C9 -180.0(2) . . . . ?
O1 C1 N1 C8 -178.9(3) . . . . ?
C2 C1 N1 C8 0.3(3) . . . . ?
O1 C1 N1 C9 1.7(4) . . . . ?
C2 C1 N1 C9 -179.1(2) . . . . ?
C10 C9 N1 C8 -78.4(3) . . . . ?
C10 C9 N1 C1 100.9(3) . . . . ?
C12 C11 N2 C14 -76.1(3) . . . . ?
C12 C11 N2 S1 79.3(3) . . . . ?
C15 C14 N2 C11 -82.6(3) . . . . ?
C15 C14 N2 S1 122.5(2) . . . . ?
O5 C16 O6 C17 0.9(4) . . . . ?
C15 C16 O6 C17 -177.7(2) . . . . ?
C18 C17 O6 C16 -60.1(3) . . . . ?
C19 C17 O6 C16 -177.4(3) . . . . ?
C20 C17 O6 C16 64.4(3) . . . . ?
C11 N2 S1 O3 36.5(2) . . . . ?
C14 N2 S1 O3 -169.00(19) . . . . ?
C11 N2 S1 O4 165.53(19) . . . . ?
C14 N2 S1 O4 -40.0(2) . . . . ?
C11 N2 S1 C10 -79.2(2) . . . . ?
C14 N2 S1 C10 75.3(2) . . . . ?
C9 C10 S1 O3 62.6(2) . . . . ?
C9 C10 S1 O4 -65.9(2) . . . . ?
C9 C10 S1 N2 178.70(17) . . . . ?

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
C11 H11B O1 0.97 2.35 3.140(3) 137.5 4_464
C18 H18B O5 0.96 2.44 2.967(4) 114.0 .
C20 H20B O5 0.96 2.47 3.041(4) 118.3 .

_diffrn_measured_fraction_theta_max 0.888
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.888
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.025
_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.888       
RESPONSE: Probably a bug in the data collection strategy.
;
# end Validation Reply Form

_database_code_depnum_ccdc_archive 'CCDC 968920'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N O4 S'
_chemical_formula_weight         295.35
_chemical_absolute_configuration ad


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           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_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                   6.53780(10)
_cell_length_b                   12.7943(3)
_cell_length_c                   17.9426(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1500.84(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2230
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9289
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2616
_reflns_number_gt                2487
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0469P)²+0.1769P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.1954(4) 0.4615(2) 0.24439(10) 0.0710(6) Uani 1 1 d . . .
H1A H 0.3261 0.4402 0.2635 0.106 Uiso 1 1 calc R . .
H1B H 0.1126 0.4008 0.2353 0.106 Uiso 1 1 calc R . .
H1C H 0.1286 0.5056 0.2802 0.106 Uiso 1 1 calc R . .
C2 C 0.2553(2) 0.38417(11) 0.05328(7) 0.0349(3) Uani 1 1 d . . .
H2 H 0.1087 0.3999 0.0557 0.042 Uiso 1 1 calc R . .
C3 C 0.2819(2) 0.27105(12) 0.07727(9) 0.0403(4) Uani 1 1 d . . .
C4 C 0.2469(5) 0.15646(15) 0.18024(13) 0.0752(7) Uani 1 1 d . . .
H4A H 0.1701 0.1041 0.1541 0.113 Uiso 1 1 calc R . .
H4B H 0.2035 0.1588 0.2313 0.113 Uiso 1 1 calc R . .
H4C H 0.3899 0.1397 0.1781 0.113 Uiso 1 1 calc R . .
C5 C 0.3234(3) 0.40154(13) -0.02757(9) 0.0435(4) Uani 1 1 d . . .
H5A H 0.4663 0.3824 -0.0325 0.052 Uiso 1 1 calc R . .
H5B H 0.2445 0.3564 -0.0601 0.052 Uiso 1 1 calc R . .
C6 C 0.2956(3) 0.51375(13) -0.05175(8) 0.0415(4) Uani 1 1 d . . .
C7 C 0.1021(3) 0.55314(17) -0.06475(11) 0.0543(5) Uani 1 1 d . . .
H7 H -0.0115 0.5101 -0.0591 0.065 Uiso 1 1 calc R . .
C8 C 0.0761(4) 0.6562(2) -0.08606(12) 0.0696(6) Uani 1 1 d . . .
H8 H -0.0547 0.6817 -0.0953 0.084 Uiso 1 1 calc R . .
C9 C 0.2408(4) 0.72063(16) -0.09368(11) 0.0711(6) Uani 1 1 d . . .
H9 H 0.2221 0.7899 -0.1079 0.085 Uiso 1 1 calc R . .
C10 C 0.4330(4) 0.68348(18) -0.08047(12) 0.0671(6) Uani 1 1 d . . .
H10 H 0.5454 0.7275 -0.0855 0.081 Uiso 1 1 calc R . .
C11 C 0.4605(3) 0.58051(17) -0.05969(11) 0.0555(5) Uani 1 1 d . . .
H11 H 0.5920 0.5557 -0.0509 0.067 Uiso 1 1 calc R . .
C12 C 0.5818(3) 0.44759(14) 0.11362(10) 0.0457(4) Uani 1 1 d . . .
H12A H 0.6421 0.4281 0.0662 0.055 Uiso 1 1 calc R . .
H12B H 0.6356 0.5157 0.1272 0.055 Uiso 1 1 calc R . .
C13 C 0.6453(3) 0.37162(17) 0.17003(12) 0.0571(5) Uani 1 1 d . . .
C14 C 0.6942(4) 0.3112(2) 0.21540(17) 0.0908(9) Uani 1 1 d . . .
N1 N 0.35883(19) 0.45626(10) 0.10411(7) 0.0349(3) Uani 1 1 d . . .
O1 O 0.3564(3) 0.61862(12) 0.17611(10) 0.0806(5) Uani 1 1 d . . .
O2 O 0.0325(2) 0.54660(12) 0.12864(8) 0.0615(4) Uani 1 1 d . . .
O3 O 0.3519(2) 0.20283(10) 0.03921(8) 0.0596(4) Uani 1 1 d . . .
O4 O 0.2126(2) 0.25701(10) 0.14600(7) 0.0559(3) Uani 1 1 d . . .
S1 S 0.22980(7) 0.53053(3) 0.16074(2) 0.04582(15) Uani 1 1 d . . .
H14 H 0.720(5) 0.266(2) 0.2497(18) 0.119(11) Uiso 1 1 d . . .


_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
C1 S1 1.756(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.4631(19) . ?
C2 C3 1.520(2) . ?
C2 C5 1.534(2) . ?
C2 H2 0.9800 . ?
C3 O3 1.199(2) . ?
C3 O4 1.326(2) . ?
C4 O4 1.443(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.511(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.382(3) . ?
C6 C11 1.383(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.463(3) . ?
C12 N1 1.472(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.167(3) . ?
C14 H14 0.86(3) . ?
N1 S1 1.6269(13) . ?
O1 S1 1.4253(16) . ?
O2 S1 1.4275(15) . ?

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
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 111.77(12) . . ?
N1 C2 C5 111.35(13) . . ?
C3 C2 C5 111.87(13) . . ?
N1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C5 C2 H2 107.2 . . ?
O3 C3 O4 124.17(16) . . ?
O3 C3 C2 125.14(15) . . ?
O4 C3 C2 110.68(14) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 111.99(14) . . ?
C6 C5 H5A 109.2 . . ?
C2 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C2 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C11 118.11(17) . . ?
C7 C6 C5 120.33(16) . . ?
C11 C6 C5 121.54(17) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.98(19) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 N1 114.28(15) . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
N1 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 179.3(3) . . ?
C13 C14 H14 176(2) . . ?
C2 N1 C12 118.88(13) . . ?
C2 N1 S1 121.17(10) . . ?
C12 N1 S1 119.02(11) . . ?
C3 O4 C4 117.61(16) . . ?
O1 S1 O2 119.26(11) . . ?
O1 S1 N1 106.36(9) . . ?
O2 S1 N1 107.50(7) . . ?
O1 S1 C1 107.87(12) . . ?
O2 S1 C1 107.54(10) . . ?
N1 S1 C1 107.85(9) . . ?

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
N1 C2 C3 O3 -123.91(18) . . . . ?
C5 C2 C3 O3 1.7(2) . . . . ?
N1 C2 C3 O4 57.48(17) . . . . ?
C5 C2 C3 O4 -176.88(14) . . . . ?
N1 C2 C5 C6 -54.55(19) . . . . ?
C3 C2 C5 C6 179.58(14) . . . . ?
C2 C5 C6 C7 -72.4(2) . . . . ?
C2 C5 C6 C11 105.97(19) . . . . ?
C11 C6 C7 C8 0.8(3) . . . . ?
C5 C6 C7 C8 179.25(17) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C7 C6 C11 C10 -0.4(3) . . . . ?
C5 C6 C11 C10 -178.77(17) . . . . ?
N1 C12 C13 C14 -32(25) . . . . ?
C3 C2 N1 C12 60.77(17) . . . . ?
C5 C2 N1 C12 -65.15(18) . . . . ?
C3 C2 N1 S1 -108.09(13) . . . . ?
C5 C2 N1 S1 125.99(12) . . . . ?
C13 C12 N1 C2 -86.05(19) . . . . ?
C13 C12 N1 S1 83.05(18) . . . . ?
O3 C3 O4 C4 8.0(3) . . . . ?
C2 C3 O4 C4 -173.37(17) . . . . ?
C2 N1 S1 O1 -154.67(13) . . . . ?
C12 N1 S1 O1 36.49(15) . . . . ?
C2 N1 S1 O2 -25.86(14) . . . . ?
C12 N1 S1 O2 165.30(13) . . . . ?
C2 N1 S1 C1 89.83(15) . . . . ?
C12 N1 S1 C1 -79.01(15) . . . . ?

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
C1 H1B O4 0.96 2.53 3.158(3) 123.4 .
C2 H2 O2 0.98 2.34 2.8755(19) 113.4 .
C12 H12B O2 0.97 2.63 3.219(2) 119.8 1_655

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 969104'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N O4 S'
_chemical_formula_weight         295.35
_chemical_absolute_configuration ad


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           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_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                   6.5396(2)
_cell_length_b                   12.8007(6)
_cell_length_c                   17.9487(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1502.51(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2340
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      24.8

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5389
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2507
_reflns_number_gt                2354
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0433P)²+0.2637P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.0069(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(8)
_refine_ls_number_reflns         2507
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
C1 C 0.6965(4) 0.5382(2) 0.24447(11) 0.0702(7) Uani 1 1 d . . .
H1A H 0.6332 0.4933 0.2806 0.105 Uiso 1 1 calc R . .
H1B H 0.6108 0.5978 0.2358 0.105 Uiso 1 1 calc R . .
H1C H 0.8270 0.5609 0.2628 0.105 Uiso 1 1 calc R . .
C2 C 0.7550(3) 0.61568(12) 0.05321(9) 0.0345(4) Uani 1 1 d . . .
H2 H 0.6085 0.5999 0.0555 0.041 Uiso 1 1 calc R . .
C3 C 0.7817(3) 0.72916(13) 0.07741(10) 0.0397(4) Uani 1 1 d . . .
C4 C 0.7473(5) 0.84375(17) 0.18015(14) 0.0746(8) Uani 1 1 d . . .
H4A H 0.8903 0.8604 0.1780 0.112 Uiso 1 1 calc R . .
H4B H 0.7039 0.8417 0.2312 0.112 Uiso 1 1 calc R . .
H4C H 0.6707 0.8961 0.1539 0.112 Uiso 1 1 calc R . .
C5 C 0.8234(3) 0.59859(15) -0.02749(11) 0.0436(5) Uani 1 1 d . . .
H5A H 0.7447 0.6438 -0.0601 0.052 Uiso 1 1 calc R . .
H5B H 0.9664 0.6176 -0.0323 0.052 Uiso 1 1 calc R . .
C6 C 0.7954(3) 0.48609(14) -0.05166(9) 0.0411(5) Uani 1 1 d . . .
C7 C 0.9602(4) 0.41967(18) -0.05975(13) 0.0547(6) Uani 1 1 d . . .
H7 H 1.0916 0.4446 -0.0511 0.066 Uiso 1 1 calc R . .
C8 C 0.9328(5) 0.3168(2) -0.08041(14) 0.0670(7) Uani 1 1 d . . .
H8 H 1.0454 0.2730 -0.0854 0.080 Uiso 1 1 calc R . .
C9 C 0.7412(5) 0.27926(17) -0.09350(13) 0.0707(7) Uani 1 1 d . . .
H9 H 0.7230 0.2099 -0.1075 0.085 Uiso 1 1 calc R . .
C10 C 0.5766(5) 0.3434(2) -0.08607(14) 0.0694(7) Uani 1 1 d . . .
H10 H 0.4460 0.3178 -0.0954 0.083 Uiso 1 1 calc R . .
C11 C 0.6024(4) 0.44683(19) -0.06463(13) 0.0547(6) Uani 1 1 d . . .
H11 H 0.4888 0.4898 -0.0590 0.066 Uiso 1 1 calc R . .
C12 C 1.0819(3) 0.55261(16) 0.11353(12) 0.0459(5) Uani 1 1 d . . .
H12A H 1.1361 0.4846 0.1268 0.055 Uiso 1 1 calc R . .
H12B H 1.1418 0.5723 0.0661 0.055 Uiso 1 1 calc R . .
C13 C 1.1456(3) 0.62843(18) 0.17006(15) 0.0570(6) Uani 1 1 d . . .
C14 C 1.1949(5) 0.6887(3) 0.2156(2) 0.0908(11) Uani 1 1 d . . .
N1 N 0.8589(2) 0.54374(11) 0.10424(8) 0.0349(3) Uani 1 1 d . . .
O1 O 0.5326(2) 0.45329(13) 0.12875(9) 0.0615(4) Uani 1 1 d . . .
O2 O 0.8567(3) 0.38124(13) 0.17609(11) 0.0814(6) Uani 1 1 d . . .
O3 O 0.8518(3) 0.79727(11) 0.03921(9) 0.0596(4) Uani 1 1 d . . .
O4 O 0.7127(3) 0.74288(11) 0.14607(8) 0.0557(4) Uani 1 1 d . . .
S1 S 0.73013(8) 0.46951(4) 0.16081(2) 0.04534(16) Uani 1 1 d . . .
H14 H 1.226(5) 0.735(3) 0.2467(18) 0.107(11) Uiso 1 1 d . . .


_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
C1 S1 1.754(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.466(2) . ?
C2 C3 1.526(2) . ?
C2 C5 1.532(3) . ?
C2 H2 0.9800 . ?
C3 O3 1.200(2) . ?
C3 O4 1.324(2) . ?
C4 O4 1.447(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.515(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.378(3) . ?
C6 C7 1.380(3) . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.362(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.465(3) . ?
C12 N1 1.473(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.168(4) . ?
C14 H14 0.84(3) . ?
N1 S1 1.6257(15) . ?
O1 S1 1.4295(17) . ?
O2 S1 1.4272(18) . ?

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
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 111.54(14) . . ?
N1 C2 C5 111.46(14) . . ?
C3 C2 C5 111.82(14) . . ?
N1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C5 C2 H2 107.2 . . ?
O3 C3 O4 124.44(18) . . ?
O3 C3 C2 124.92(17) . . ?
O4 C3 C2 110.62(15) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 111.79(16) . . ?
C6 C5 H5A 109.3 . . ?
C2 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C2 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C11 C6 C7 118.20(19) . . ?
C11 C6 C5 120.37(19) . . ?
C7 C6 C5 121.41(19) . . ?
C6 C7 C8 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 120.3(2) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 N1 114.28(17) . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
N1 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 179.4(3) . . ?
C13 C14 H14 177(2) . . ?
C2 N1 C12 118.77(15) . . ?
C2 N1 S1 121.18(12) . . ?
C12 N1 S1 119.16(13) . . ?
C3 O4 C4 117.31(18) . . ?
O2 S1 O1 119.12(12) . . ?
O2 S1 N1 106.41(10) . . ?
O1 S1 N1 107.54(8) . . ?
O2 S1 C1 107.76(13) . . ?
O1 S1 C1 107.69(12) . . ?
N1 S1 C1 107.87(10) . . ?

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
N1 C2 C3 O3 124.0(2) . . . . ?
C5 C2 C3 O3 -1.6(3) . . . . ?
N1 C2 C3 O4 -57.3(2) . . . . ?
C5 C2 C3 O4 177.09(16) . . . . ?
N1 C2 C5 C6 54.8(2) . . . . ?
C3 C2 C5 C6 -179.57(16) . . . . ?
C2 C5 C6 C11 72.3(2) . . . . ?
C2 C5 C6 C7 -106.3(2) . . . . ?
C11 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C7 C8 178.8(2) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
C5 C6 C11 C10 -179.4(2) . . . . ?
C9 C10 C11 C6 0.9(4) . . . . ?
N1 C12 C13 C14 35(30) . . . . ?
C3 C2 N1 C12 -61.0(2) . . . . ?
C5 C2 N1 C12 64.8(2) . . . . ?
C3 C2 N1 S1 108.13(16) . . . . ?
C5 C2 N1 S1 -126.09(14) . . . . ?
C13 C12 N1 C2 86.4(2) . . . . ?
C13 C12 N1 S1 -82.9(2) . . . . ?
O3 C3 O4 C4 -7.9(3) . . . . ?
C2 C3 O4 C4 173.46(19) . . . . ?
C2 N1 S1 O2 154.38(15) . . . . ?
C12 N1 S1 O2 -36.56(17) . . . . ?
C2 N1 S1 O1 25.69(15) . . . . ?
C12 N1 S1 O1 -165.25(14) . . . . ?
C2 N1 S1 C1 -90.22(17) . . . . ?
C12 N1 S1 C1 78.84(17) . . . . ?

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
C1 H1B O4 0.96 2.55 3.162(3) 122.0 .
C2 H2 O1 0.98 2.34 2.877(2) 113.4 .
C12 H12A O1 0.97 2.62 3.221(3) 120.1 1_655

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 969105'
