# Electronic Supplementary Material (ESI) for RSC Advances.
# 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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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_sad

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N2 O3 S'
_chemical_formula_sum            'C21 H22 N2 O3 S'
_chemical_formula_weight         382.47

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2bc'

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'
'-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                   10.0704(16)
_cell_length_b                   16.864(3)
_cell_length_c                   22.682(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3852.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3702
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      21.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   'SADABS (Bruker 2002)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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 Smart Apex DDC'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28000
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3789
_reflns_number_gt                2736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

_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)+(0.0572P)²+0.6891P] 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       ?
_refine_ls_number_reflns         3789
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
S1 S 0.83707(5) 0.16858(3) 0.26044(2) 0.03779(16) Uani 1 1 d . . .
O3 O 0.95067(13) 0.21946(8) 0.26049(6) 0.0466(4) Uani 1 1 d . . .
O2 O 0.78535(14) 0.14357(9) 0.20483(6) 0.0490(4) Uani 1 1 d . . .
N1 N 0.71563(15) 0.21479(10) 0.29222(8) 0.0419(4) Uani 1 1 d . . .
H1 H 0.6414 0.2032 0.2767 0.063 Uiso 1 1 d R . .
N2 N 0.67247(16) 0.01812(10) 0.27753(8) 0.0470(5) Uani 1 1 d . . .
H2A H 0.6717 0.0438 0.2453 0.071 Uiso 1 1 d R . .
C1 C 0.87510(18) 0.08715(11) 0.30490(8) 0.0360(5) Uani 1 1 d . . .
C2 C 0.99232(19) 0.08974(12) 0.33744(9) 0.0408(5) Uani 1 1 d . . .
H2 H 1.0471 0.1340 0.3348 0.049 Uiso 1 1 calc R . .
C15 C 0.71338(19) 0.23772(11) 0.35245(9) 0.0395(5) Uani 1 1 d . . .
C6 C 0.78840(18) 0.02141(12) 0.30901(9) 0.0390(5) Uani 1 1 d . . .
C16 C 0.8243(2) 0.26706(12) 0.38072(10) 0.0462(5) Uani 1 1 d . . .
H16 H 0.9050 0.2702 0.3610 0.055 Uiso 1 1 calc R . .
C5 C 0.8265(2) -0.03905(13) 0.34763(10) 0.0470(5) Uani 1 1 d . . .
H5 H 0.7708 -0.0825 0.3526 0.056 Uiso 1 1 calc R . .
C8 C 0.49028(18) -0.06204(11) 0.32336(9) 0.0395(5) Uani 1 1 d . . .
C3 C 1.0278(2) 0.02791(13) 0.37323(9) 0.0484(5) Uani 1 1 d . . .
H3 H 1.1077 0.0290 0.3938 0.058 Uiso 1 1 calc R . .
O1 O 0.21519(16) -0.11132(12) 0.45495(8) 0.0728(5) Uani 1 1 d . . .
C11 C 0.3084(2) -0.09150(14) 0.41317(10) 0.0504(6) Uani 1 1 d . . .
C4 C 0.9433(2) -0.03606(13) 0.37833(10) 0.0510(6) Uani 1 1 d . . .
H4 H 0.9661 -0.0779 0.4031 0.061 Uiso 1 1 calc R . .
C9 C 0.3920(2) -0.11937(12) 0.31729(10) 0.0460(5) Uani 1 1 d . . .
H9 H 0.3871 -0.1485 0.2825 0.055 Uiso 1 1 calc R . .
C20 C 0.5939(2) 0.23382(14) 0.38224(11) 0.0553(6) Uani 1 1 d . . .
H20 H 0.5188 0.2134 0.3638 0.066 Uiso 1 1 calc R . .
C7 C 0.5906(2) -0.05292(13) 0.27440(10) 0.0471(5) Uani 1 1 d . . .
H7A H 0.6485 -0.0989 0.2747 0.057 Uiso 1 1 calc R . .
H7B H 0.5437 -0.0528 0.2371 0.057 Uiso 1 1 calc R . .
C12 C 0.4022(2) -0.03331(14) 0.41978(11) 0.0564(6) Uani 1 1 d . . .
H12 H 0.4060 -0.0038 0.4544 0.068 Uiso 1 1 calc R . .
C10 C 0.3023(2) -0.13390(14) 0.36136(11) 0.0537(6) Uani 1 1 d . . .
H10 H 0.2372 -0.1724 0.3563 0.064 Uiso 1 1 calc R . .
C17 C 0.8144(3) 0.29175(13) 0.43856(11) 0.0566(6) Uani 1 1 d . . .
H17 H 0.8900 0.3107 0.4575 0.068 Uiso 1 1 calc R . .
C13 C 0.4917(2) -0.01867(13) 0.37425(10) 0.0530(6) Uani 1 1 d . . .
H13 H 0.5539 0.0216 0.3786 0.064 Uiso 1 1 calc R . .
C18 C 0.6966(3) 0.28925(14) 0.46925(11) 0.0613(7) Uani 1 1 d . . .
C19 C 0.5869(3) 0.26042(15) 0.43957(12) 0.0665(7) Uani 1 1 d . . .
H19 H 0.5056 0.2589 0.4590 0.080 Uiso 1 1 calc R . .
C14 C 0.2245(3) -0.0758(2) 0.51091(13) 0.0923(10) Uani 1 1 d . . .
H14A H 0.1538 -0.0948 0.5355 0.138 Uiso 1 1 calc R . .
H14B H 0.2176 -0.0192 0.5069 0.138 Uiso 1 1 calc R . .
H14C H 0.3083 -0.0890 0.5285 0.138 Uiso 1 1 calc R . .
C21 C 0.6868(4) 0.31760(19) 0.53208(13) 0.0954(10) Uani 1 1 d . . .
H21A H 0.7725 0.3351 0.5453 0.143 Uiso 1 1 calc R . .
H21B H 0.6567 0.2749 0.5567 0.143 Uiso 1 1 calc R . .
H21C H 0.6249 0.3608 0.5343 0.143 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 O2 1.4284(15) . ?
S1 O3 1.4300(14) . ?
S1 N1 1.6195(17) . ?
S1 C1 1.746(2) . ?
N1 C15 1.420(3) . ?
N1 H1 0.8492 . ?
N2 C6 1.370(2) . ?
N2 C7 1.456(2) . ?
N2 H2A 0.8500 . ?
C1 C2 1.393(3) . ?
C1 C6 1.414(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C15 C16 1.380(3) . ?
C15 C20 1.382(3) . ?
C6 C5 1.398(3) . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C5 C4 1.367(3) . ?
C5 H5 0.9300 . ?
C8 C13 1.367(3) . ?
C8 C9 1.390(3) . ?
C8 C7 1.509(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
O1 C11 1.375(3) . ?
O1 C14 1.407(3) . ?
C11 C12 1.370(3) . ?
C11 C10 1.377(3) . ?
C4 H4 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9300 . ?
C20 C19 1.377(3) . ?
C20 H20 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
C18 C19 1.381(4) . ?
C18 C21 1.506(4) . ?
C19 H19 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
O2 S1 O3 118.01(9) . . ?
O2 S1 N1 105.06(9) . . ?
O3 S1 N1 108.36(9) . . ?
O2 S1 C1 110.96(9) . . ?
O3 S1 C1 107.21(9) . . ?
N1 S1 C1 106.67(9) . . ?
C15 N1 S1 124.84(13) . . ?
C15 N1 H1 116.6 . . ?
S1 N1 H1 111.7 . . ?
C6 N2 C7 122.77(17) . . ?
C6 N2 H2A 115.8 . . ?
C7 N2 H2A 111.8 . . ?
C2 C1 C6 120.86(18) . . ?
C2 C1 S1 117.85(15) . . ?
C6 C1 S1 121.27(14) . . ?
C3 C2 C1 120.76(19) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C16 C15 C20 119.7(2) . . ?
C16 C15 N1 122.14(18) . . ?
C20 C15 N1 118.12(19) . . ?
N2 C6 C5 122.09(18) . . ?
N2 C6 C1 121.58(18) . . ?
C5 C6 C1 116.33(18) . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C13 C8 C9 117.6(2) . . ?
C13 C8 C7 124.07(18) . . ?
C9 C8 C7 118.33(19) . . ?
C2 C3 C4 118.98(19) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C11 O1 C14 118.2(2) . . ?
C12 C11 O1 124.7(2) . . ?
C12 C11 C10 119.7(2) . . ?
O1 C11 C10 115.6(2) . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C19 C20 C15 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
N2 C7 C8 115.29(18) . . ?
N2 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
N2 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C18 C17 C16 122.2(2) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C8 C13 C12 121.7(2) . . ?
C8 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C17 C18 C19 117.0(2) . . ?
C17 C18 C21 121.7(3) . . ?
C19 C18 C21 121.4(3) . . ?
C20 C19 C18 122.3(2) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 1010819'
