# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_x
_database_code_depnum_ccdc_archive 'CCDC 1416587'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 N O4 S'
_chemical_formula_weight         403.44

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   P21

_chemical_absolute_configuration ad

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

_cell_length_a                   8.3300(17)
_cell_length_b                   12.431(3)
_cell_length_c                   9.5280(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.09(3)
_cell_angle_gamma                90.00
_cell_volume                     985.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3868
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_sigmaI/netI    0.0997
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.37
_reflns_number_total             3613
_reflns_number_gt                2354
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius,1994)'
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_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)+(0.1000P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.26(17)
_refine_ls_number_reflns         3613
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1891
_refine_ls_wR_factor_gt          0.1655
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.010
_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
S S 0.52522(17) 0.17169(12) 0.76852(17) 0.0604(5) Uani 1 1 d . . .
N N 0.2762(5) 0.3115(3) 0.7059(4) 0.0421(10) Uani 1 1 d . . .
O1 O 0.1854(5) 0.2414(3) 0.9138(4) 0.0630(11) Uani 1 1 d . . .
C1 C 0.3511(6) 0.2130(4) 0.6508(6) 0.0463(12) Uani 1 1 d . . .
O2 O 0.3734(5) 0.4345(3) 0.5480(4) 0.0593(10) Uani 1 1 d . . .
C2 C 0.2289(6) 0.1183(4) 0.6443(6) 0.0458(12) Uani 1 1 d . . .
O3 O 0.5411(5) 0.2283(4) 0.4647(5) 0.0694(12) Uani 1 1 d . . .
C3 C 0.0668(7) 0.1357(5) 0.6353(7) 0.0654(17) Uani 1 1 d . . .
H3A H 0.0268 0.2055 0.6393 0.079 Uiso 1 1 calc R . .
O4 O 0.2778(5) 0.2453(3) 0.4100(4) 0.0593(10) Uani 1 1 d . . .
C4 C -0.0384(8) 0.0490(6) 0.6204(7) 0.0691(18) Uani 1 1 d . . .
H4A H -0.1490 0.0597 0.6172 0.083 Uiso 1 1 calc R . .
C5 C 0.0251(10) -0.0533(6) 0.6106(7) 0.077(2) Uani 1 1 d . . .
H5A H -0.0439 -0.1119 0.5999 0.092 Uiso 1 1 calc R . .
C6 C 0.1835(8) -0.0695(5) 0.6161(7) 0.0648(16) Uani 1 1 d . . .
H6A H 0.2229 -0.1393 0.6117 0.078 Uiso 1 1 calc R . .
C7 C 0.2917(8) 0.0165(5) 0.6282(7) 0.0584(15) Uani 1 1 d . . .
H7A H 0.4019 0.0055 0.6256 0.070 Uiso 1 1 calc R . .
C8 C 0.2149(6) 0.3157(4) 0.8359(6) 0.0499(13) Uani 1 1 d . . .
C9 C 0.1865(6) 0.4331(4) 0.8678(6) 0.0493(13) Uani 1 1 d . . .
C10 C 0.1250(7) 0.4807(5) 0.9833(7) 0.0624(16) Uani 1 1 d . . .
H10A H 0.0903 0.4411 1.0587 0.075 Uiso 1 1 calc R . .
C11 C 0.1183(9) 0.5938(6) 0.9793(8) 0.074(2) Uani 1 1 d . . .
H11A H 0.0787 0.6310 1.0548 0.089 Uiso 1 1 calc R . .
C12 C 0.1689(8) 0.6501(5) 0.8663(8) 0.074(2) Uani 1 1 d . . .
H12A H 0.1617 0.7247 0.8670 0.089 Uiso 1 1 calc R . .
C13 C 0.2290(7) 0.6010(5) 0.7534(7) 0.0594(15) Uani 1 1 d . . .
H13A H 0.2623 0.6405 0.6774 0.071 Uiso 1 1 calc R . .
C14 C 0.2391(6) 0.4896(4) 0.7556(6) 0.0472(13) Uani 1 1 d . . .
C15 C 0.3053(6) 0.4170(4) 0.6536(6) 0.0430(12) Uani 1 1 d . . .
C16 C 0.4070(7) 0.2341(4) 0.5007(7) 0.0525(14) Uani 1 1 d . . .
C17 C 0.3137(10) 0.2682(7) 0.2678(7) 0.081(2) Uani 1 1 d . . .
H17A H 0.2154 0.2742 0.2110 0.122 Uiso 1 1 calc R . .
H17B H 0.3777 0.2110 0.2324 0.122 Uiso 1 1 calc R . .
H17C H 0.3722 0.3346 0.2645 0.122 Uiso 1 1 calc R . .
C18 C 0.6054(7) 0.2981(5) 0.8206(7) 0.0606(16) Uani 1 1 d . . .
C19 C 0.5702(8) 0.3352(7) 0.9560(7) 0.0741(19) Uani 1 1 d . . .
H19A H 0.5099 0.2944 1.0158 0.089 Uiso 1 1 calc R . .
C20 C 0.6304(11) 0.4357(9) 0.9950(10) 0.102(3) Uani 1 1 d . . .
H20A H 0.6084 0.4632 1.0827 0.122 Uiso 1 1 calc R . .
C21 C 0.7195(11) 0.4945(8) 0.9099(13) 0.107(3) Uani 1 1 d . . .
H21A H 0.7575 0.5612 0.9407 0.128 Uiso 1 1 calc R . .
C22 C 0.7557(11) 0.4594(7) 0.7800(10) 0.100(3) Uani 1 1 d . . .
H22A H 0.8147 0.5019 0.7212 0.120 Uiso 1 1 calc R . .
C23 C 0.7002(8) 0.3550(6) 0.7371(8) 0.075(2) Uani 1 1 d . . .
H23A H 0.7293 0.3264 0.6519 0.090 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
S C18 1.768(7) . ?
S C1 1.857(5) . ?
N C8 1.366(7) . ?
N C15 1.429(6) . ?
N C1 1.483(6) . ?
O1 C8 1.218(6) . ?
C1 C16 1.550(8) . ?
C1 C2 1.555(7) . ?
O2 C15 1.201(6) . ?
C2 C3 1.366(7) . ?
C2 C7 1.381(8) . ?
O3 C16 1.188(6) . ?
C3 C4 1.391(9) . ?
C3 H3A 0.9300 . ?
O4 C16 1.350(7) . ?
O4 C17 1.432(7) . ?
C4 C5 1.383(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.333(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.398(8) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.512(8) . ?
C9 C14 1.370(7) . ?
C9 C10 1.373(7) . ?
C10 C11 1.408(10) . ?
C10 H10A 0.9300 . ?
C11 C12 1.369(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.356(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.387(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.456(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.351(9) . ?
C18 C19 1.416(9) . ?
C19 C20 1.389(13) . ?
C19 H19A 0.9300 . ?
C20 C21 1.344(12) . ?
C20 H20A 0.9300 . ?
C21 C22 1.361(13) . ?
C21 H21A 0.9300 . ?
C22 C23 1.430(11) . ?
C22 H22A 0.9300 . ?
C23 H23A 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
C18 S C1 101.2(2) . . ?
C8 N C15 111.1(4) . . ?
C8 N C1 122.5(4) . . ?
C15 N C1 123.5(4) . . ?
N C1 C16 109.9(4) . . ?
N C1 C2 110.6(4) . . ?
C16 C1 C2 108.6(4) . . ?
N C1 S 110.1(3) . . ?
C16 C1 S 109.9(3) . . ?
C2 C1 S 107.6(4) . . ?
C3 C2 C7 121.2(5) . . ?
C3 C2 C1 121.7(5) . . ?
C7 C2 C1 116.6(5) . . ?
C2 C3 C4 119.9(6) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C16 O4 C17 115.2(5) . . ?
C5 C4 C3 118.6(6) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
C6 C5 C4 121.1(6) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C7 121.3(6) . . ?
C5 C6 H6A 119.3 . . ?
C7 C6 H6A 119.3 . . ?
C2 C7 C6 117.6(6) . . ?
C2 C7 H7A 121.2 . . ?
C6 C7 H7A 121.2 . . ?
O1 C8 N 128.4(5) . . ?
O1 C8 C9 124.8(5) . . ?
N C8 C9 106.8(4) . . ?
C14 C9 C10 123.6(5) . . ?
C14 C9 C8 106.1(5) . . ?
C10 C9 C8 130.3(5) . . ?
C9 C10 C11 115.1(6) . . ?
C9 C10 H10A 122.4 . . ?
C11 C10 H10A 122.4 . . ?
C12 C11 C10 121.2(6) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C13 C12 C11 122.4(6) . . ?
C13 C12 H12A 118.8 . . ?
C11 C12 H12A 118.8 . . ?
C12 C13 C14 117.5(6) . . ?
C12 C13 H13A 121.2 . . ?
C14 C13 H13A 121.2 . . ?
C9 C14 C13 120.1(5) . . ?
C9 C14 C15 110.6(5) . . ?
C13 C14 C15 129.3(5) . . ?
O2 C15 N 123.7(4) . . ?
O2 C15 C14 131.3(5) . . ?
N C15 C14 105.0(4) . . ?
O3 C16 O4 123.4(6) . . ?
O3 C16 C1 126.1(5) . . ?
O4 C16 C1 109.8(4) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 121.5(7) . . ?
C23 C18 S 121.6(6) . . ?
C19 C18 S 116.8(5) . . ?
C20 C19 C18 116.6(8) . . ?
C20 C19 H19A 121.7 . . ?
C18 C19 H19A 121.7 . . ?
C21 C20 C19 122.0(9) . . ?
C21 C20 H20A 119.0 . . ?
C19 C20 H20A 119.0 . . ?
C20 C21 C22 122.1(9) . . ?
C20 C21 H21A 119.0 . . ?
C22 C21 H21A 119.0 . . ?
C21 C22 C23 117.8(9) . . ?
C21 C22 H22A 121.1 . . ?
C23 C22 H22A 121.1 . . ?
C18 C23 C22 119.8(8) . . ?
C18 C23 H23A 120.1 . . ?
C22 C23 H23A 120.1 . . ?

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
C8 N C1 C16 179.5(4) . . . . ?
C15 N C1 C16 -21.5(6) . . . . ?
C8 N C1 C2 59.6(6) . . . . ?
C15 N C1 C2 -141.4(5) . . . . ?
C8 N C1 S -59.2(5) . . . . ?
C15 N C1 S 99.8(5) . . . . ?
C18 S C1 N -36.5(4) . . . . ?
C18 S C1 C16 84.7(4) . . . . ?
C18 S C1 C2 -157.2(4) . . . . ?
N C1 C2 C3 24.0(7) . . . . ?
C16 C1 C2 C3 -96.6(6) . . . . ?
S C1 C2 C3 144.4(5) . . . . ?
N C1 C2 C7 -164.7(5) . . . . ?
C16 C1 C2 C7 74.7(6) . . . . ?
S C1 C2 C7 -44.3(6) . . . . ?
C7 C2 C3 C4 4.9(9) . . . . ?
C1 C2 C3 C4 175.8(6) . . . . ?
C2 C3 C4 C5 -2.0(10) . . . . ?
C3 C4 C5 C6 0.4(11) . . . . ?
C4 C5 C6 C7 -1.7(11) . . . . ?
C3 C2 C7 C6 -6.0(9) . . . . ?
C1 C2 C7 C6 -177.3(5) . . . . ?
C5 C6 C7 C2 4.4(10) . . . . ?
C15 N C8 O1 -175.3(5) . . . . ?
C1 N C8 O1 -14.0(8) . . . . ?
C15 N C8 C9 5.5(6) . . . . ?
C1 N C8 C9 166.8(4) . . . . ?
O1 C8 C9 C14 178.5(5) . . . . ?
N C8 C9 C14 -2.2(6) . . . . ?
O1 C8 C9 C10 0.0(9) . . . . ?
N C8 C9 C10 179.2(5) . . . . ?
C14 C9 C10 C11 0.3(8) . . . . ?
C8 C9 C10 C11 178.7(6) . . . . ?
C9 C10 C11 C12 0.6(9) . . . . ?
C10 C11 C12 C13 -0.6(10) . . . . ?
C11 C12 C13 C14 -0.4(10) . . . . ?
C10 C9 C14 C13 -1.3(9) . . . . ?
C8 C9 C14 C13 -180.0(5) . . . . ?
C10 C9 C14 C15 177.0(5) . . . . ?
C8 C9 C14 C15 -1.8(6) . . . . ?
C12 C13 C14 C9 1.3(9) . . . . ?
C12 C13 C14 C15 -176.6(6) . . . . ?
C8 N C15 O2 172.4(5) . . . . ?
C1 N C15 O2 11.2(8) . . . . ?
C8 N C15 C14 -6.4(6) . . . . ?
C1 N C15 C14 -167.6(4) . . . . ?
C9 C14 C15 O2 -173.8(6) . . . . ?
C13 C14 C15 O2 4.2(11) . . . . ?
C9 C14 C15 N 4.9(6) . . . . ?
C13 C14 C15 N -177.1(6) . . . . ?
C17 O4 C16 O3 -10.2(8) . . . . ?
C17 O4 C16 C1 178.4(5) . . . . ?
N C1 C16 O3 119.4(6) . . . . ?
C2 C1 C16 O3 -119.5(6) . . . . ?
S C1 C16 O3 -2.0(7) . . . . ?
N C1 C16 O4 -69.5(5) . . . . ?
C2 C1 C16 O4 51.6(5) . . . . ?
S C1 C16 O4 169.2(4) . . . . ?
C1 S C18 C23 -80.4(6) . . . . ?
C1 S C18 C19 101.8(5) . . . . ?
C23 C18 C19 C20 3.6(10) . . . . ?
S C18 C19 C20 -178.6(5) . . . . ?
C18 C19 C20 C21 -0.9(12) . . . . ?
C19 C20 C21 C22 0.2(14) . . . . ?
C20 C21 C22 C23 -2.0(13) . . . . ?
C19 C18 C23 C22 -5.5(10) . . . . ?
S C18 C23 C22 176.8(6) . . . . ?
C21 C22 C23 C18 4.6(11) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.088
