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

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#                                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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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data_bo2735

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O4 S'
_chemical_formula_weight         369.42

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   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.5171(15)
_cell_length_b                   8.125(2)
_cell_length_c                   10.508(3)
_cell_angle_alpha                99.439(3)
_cell_angle_beta                 104.410(4)
_cell_angle_gamma                94.540(3)
_cell_volume                     446.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1891
_cell_measurement_theta_min      2.955
_cell_measurement_theta_max      31.502

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             194
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.9036
_exptl_absorpt_correction_T_max  0.9501
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5973
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4453
_reflns_number_gt                4174
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0215P)²+0.0506P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_number_reflns         4453
_refine_ls_number_parameters     235
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.16994(5) 0.32054(4) 0.65780(3) 0.02244(8) Uani 1 1 d . . .
O1 O 0.8405(2) 0.58802(16) 1.30642(11) 0.0382(3) Uani 1 1 d . . .
O2 O 0.5173(2) 0.43784(15) 1.14652(12) 0.0340(3) Uani 1 1 d . . .
O3 O 0.9432(2) 0.59852(15) 0.90336(11) 0.0339(3) Uani 1 1 d . . .
O4 O -0.2583(2) 0.17101(17) 0.44720(12) 0.0391(3) Uani 1 1 d . . .
N1 N 0.8410(2) 0.59159(15) 1.09532(12) 0.0230(3) Uani 1 1 d . . .
C1 C 1.0568(4) 0.7039(2) 1.31410(18) 0.0456(5) Uani 1 1 d . . .
H1A H 1.2106 0.6729 1.3720 0.055 Uiso 1 1 calc R . .
H1B H 1.0334 0.8197 1.3516 0.055 Uiso 1 1 calc R . .
C2 C 1.0797(3) 0.6926(2) 1.17207(16) 0.0329(4) Uani 1 1 d . . .
H2A H 1.0942 0.8051 1.1481 0.040 Uiso 1 1 calc R . .
H2B H 1.2261 0.6356 1.1589 0.040 Uiso 1 1 calc R . .
C3 C 0.7114(3) 0.5294(2) 1.17770(15) 0.0266(3) Uani 1 1 d . . .
C4 C 0.7839(3) 0.55250(18) 0.95560(14) 0.0224(3) Uani 1 1 d . . .
C5 C 0.5295(3) 0.4588(2) 0.88037(15) 0.0223(3) Uani 1 1 d . . .
H5A H 0.3974 0.5164 0.9115 0.027 Uiso 1 1 calc R . .
H5B H 0.5188 0.3438 0.9002 0.027 Uiso 1 1 calc R . .
C6 C 0.4794(3) 0.44717(17) 0.72860(14) 0.0197(3) Uani 1 1 d . . .
H6 H 0.6097 0.3857 0.6968 0.024 Uiso 1 1 calc R . .
C7 C 0.4794(2) 0.61665(16) 0.68589(13) 0.0184(3) Uani 1 1 d . . .
C8 C 0.6439(3) 0.66235(19) 0.61308(14) 0.0240(3) Uani 1 1 d . . .
H8 H 0.7531 0.5860 0.5880 0.029 Uiso 1 1 calc R . .
C9 C 0.6492(3) 0.8188(2) 0.57691(16) 0.0272(3) Uani 1 1 d . . .
H9 H 0.7621 0.8489 0.5271 0.033 Uiso 1 1 calc R . .
C10 C 0.4917(3) 0.93158(18) 0.61268(15) 0.0268(3) Uani 1 1 d . . .
H10 H 0.4990 1.0398 0.5896 0.032 Uiso 1 1 calc R . .
C11 C 0.3230(3) 0.88535(19) 0.68250(16) 0.0241(3) Uani 1 1 d . . .
H11 H 0.2119 0.9613 0.7059 0.029 Uiso 1 1 calc R . .
C12 C 0.3158(3) 0.72839(16) 0.71841(14) 0.0207(3) Uani 1 1 d . . .
H12 H 0.1986 0.6971 0.7655 0.025 Uiso 1 1 calc R . .
C13 C 0.1610(3) 0.29914(18) 0.48291(14) 0.0226(3) Uani 1 1 d . . .
H13A H 0.1811 0.4119 0.4599 0.027 Uiso 1 1 calc R . .
H13B H 0.3019 0.2392 0.4650 0.027 Uiso 1 1 calc R . .
C14 C -0.0868(3) 0.20249(17) 0.39790(15) 0.0232(3) Uani 1 1 d . . .
C15 C -0.1147(3) 0.14582(17) 0.25206(15) 0.0226(3) Uani 1 1 d . . .
C16 C 0.0629(3) 0.19863(19) 0.18891(15) 0.0270(3) Uani 1 1 d . . .
H16 H 0.2102 0.2721 0.2393 0.032 Uiso 1 1 calc R . .
C17 C 0.0254(3) 0.1441(2) 0.05215(16) 0.0350(4) Uani 1 1 d . . .
H17 H 0.1457 0.1817 0.0090 0.042 Uiso 1 1 calc R . .
C18 C -0.1870(3) 0.0353(2) -0.02091(17) 0.0388(4) Uani 1 1 d . . .
H18 H -0.2114 -0.0030 -0.1141 0.047 Uiso 1 1 calc R . .
C19 C -0.3640(3) -0.0180(2) 0.04129(17) 0.0371(4) Uani 1 1 d . . .
H19 H -0.5098 -0.0928 -0.0093 0.045 Uiso 1 1 calc R . .
C20 C -0.3293(3) 0.0374(2) 0.17656(16) 0.0298(3) Uani 1 1 d . . .
H20 H -0.4525 0.0016 0.2186 0.036 Uiso 1 1 calc R . .


_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 C13 1.8053(15) . ?
S1 C6 1.8344(15) . ?
O1 C3 1.3488(19) . ?
O1 C1 1.437(2) . ?
O2 C3 1.195(2) . ?
O3 C4 1.2117(18) . ?
O4 C14 1.2161(18) . ?
N1 C3 1.3819(19) . ?
N1 C4 1.3989(18) . ?
N1 C2 1.463(2) . ?
C1 C2 1.517(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.502(2) . ?
C5 C6 1.535(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5167(19) . ?
C6 H6 1.0000 . ?
C7 C8 1.3903(18) . ?
C7 C12 1.3915(19) . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.509(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.491(2) . ?
C15 C16 1.391(2) . ?
C15 C20 1.3947(19) . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C13 S1 C6 98.36(7) . . ?
C3 O1 C1 110.47(13) . . ?
C3 N1 C4 127.84(13) . . ?
C3 N1 C2 111.72(13) . . ?
C4 N1 C2 119.95(13) . . ?
O1 C1 C2 106.39(13) . . ?
O1 C1 H1A 110.4 . . ?
C2 C1 H1A 110.5 . . ?
O1 C1 H1B 110.4 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.6 . . ?
N1 C2 C1 101.28(14) . . ?
N1 C2 H2A 111.5 . . ?
C1 C2 H2A 111.5 . . ?
N1 C2 H2B 111.5 . . ?
C1 C2 H2B 111.5 . . ?
H2A C2 H2B 109.3 . . ?
O2 C3 O1 122.62(15) . . ?
O2 C3 N1 128.33(15) . . ?
O1 C3 N1 109.05(14) . . ?
O3 C4 N1 117.45(14) . . ?
O3 C4 C5 124.40(13) . . ?
N1 C4 C5 118.14(12) . . ?
C4 C5 C6 112.20(12) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 113.77(11) . . ?
C7 C6 S1 110.96(10) . . ?
C5 C6 S1 104.63(10) . . ?
C7 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
S1 C6 H6 109.1 . . ?
C8 C7 C12 119.00(12) . . ?
C8 C7 C6 120.09(12) . . ?
C12 C7 C6 120.91(12) . . ?
C9 C8 C7 120.28(14) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.62(14) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.40(14) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.24(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.42(13) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 S1 109.87(10) . . ?
C14 C13 H13A 109.7 . . ?
S1 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
S1 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
O4 C14 C15 121.01(13) . . ?
O4 C14 C13 120.84(14) . . ?
C15 C14 C13 118.14(12) . . ?
C16 C15 C20 119.16(14) . . ?
C16 C15 C14 122.53(13) . . ?
C20 C15 C14 118.31(13) . . ?
C17 C16 C15 120.15(14) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.95(16) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.20(16) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.08(15) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.46(16) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?

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
C3 O1 C1 C2 -9.3(2) . . . . ?
C3 N1 C2 C1 -8.12(17) . . . . ?
C4 N1 C2 C1 179.27(13) . . . . ?
O1 C1 C2 N1 10.10(18) . . . . ?
C1 O1 C3 O2 -176.11(16) . . . . ?
C1 O1 C3 N1 4.24(18) . . . . ?
C4 N1 C3 O2 -4.8(3) . . . . ?
C2 N1 C3 O2 -176.73(16) . . . . ?
C4 N1 C3 O1 174.79(14) . . . . ?
C2 N1 C3 O1 2.90(17) . . . . ?
C3 N1 C4 O3 -167.96(14) . . . . ?
C2 N1 C4 O3 3.3(2) . . . . ?
C3 N1 C4 C5 12.8(2) . . . . ?
C2 N1 C4 C5 -175.87(14) . . . . ?
O3 C4 C5 C6 -7.4(2) . . . . ?
N1 C4 C5 C6 171.77(12) . . . . ?
C4 C5 C6 C7 -61.46(16) . . . . ?
C4 C5 C6 S1 177.28(11) . . . . ?
C13 S1 C6 C7 63.48(11) . . . . ?
C13 S1 C6 C5 -173.42(10) . . . . ?
C5 C6 C7 C8 122.61(14) . . . . ?
S1 C6 C7 C8 -119.73(13) . . . . ?
C5 C6 C7 C12 -57.47(17) . . . . ?
S1 C6 C7 C12 60.19(15) . . . . ?
C12 C7 C8 C9 1.8(2) . . . . ?
C6 C7 C8 C9 -178.29(13) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C11 -1.6(2) . . . . ?
C9 C10 C11 C12 1.2(2) . . . . ?
C10 C11 C12 C7 0.6(2) . . . . ?
C8 C7 C12 C11 -2.1(2) . . . . ?
C6 C7 C12 C11 177.94(13) . . . . ?
C6 S1 C13 C14 -177.74(10) . . . . ?
S1 C13 C14 O4 9.88(18) . . . . ?
S1 C13 C14 C15 -169.73(11) . . . . ?
O4 C14 C15 C16 170.98(15) . . . . ?
C13 C14 C15 C16 -9.4(2) . . . . ?
O4 C14 C15 C20 -8.2(2) . . . . ?
C13 C14 C15 C20 171.45(13) . . . . ?
C20 C15 C16 C17 0.2(2) . . . . ?
C14 C15 C16 C17 -178.90(15) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C15 -0.7(3) . . . . ?
C16 C15 C20 C19 0.6(2) . . . . ?
C14 C15 C20 C19 179.77(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 982304'
