# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_sj-2b
_database_code_depnum_ccdc_archive 'CCDC 1476660'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 O S'
_chemical_formula_sum            'C21 H16 O S'
_chemical_formula_weight         316.40

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'
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/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.3396(10)
_cell_length_b                   8.2529(7)
_cell_length_c                   15.4875(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.937(8)
_cell_angle_gamma                90.00
_cell_volume                     1698.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1730
_cell_measurement_theta_min      3.9680
_cell_measurement_theta_max      28.2440

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64599
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6451
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3333
_reflns_number_gt                1948
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'

_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)+(0.0596P)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_number_reflns         3333
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.001

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 0.51856(5) 0.85762(9) 0.09009(5) 0.0633(3) Uani 1 1 d . . .
C17 C 0.41896(19) 0.6215(3) -0.11162(18) 0.0508(7) Uani 1 1 d . . .
C4 C 0.3584(2) 0.8495(3) 0.16948(17) 0.0518(7) Uani 1 1 d . . .
C18 C 0.4129(2) 0.5392(3) -0.19421(18) 0.0512(7) Uani 1 1 d . . .
C16 C 0.41940(18) 0.6841(3) -0.04260(18) 0.0508(7) Uani 1 1 d . . .
C10 C 0.30382(19) 0.4074(3) 0.05918(17) 0.0515(7) Uani 1 1 d . . .
H10 H 0.3654 0.4436 0.0847 0.062 Uiso 1 1 calc R . .
C3 C 0.33654(18) 0.7617(3) 0.09071(16) 0.0464(6) Uani 1 1 d . . .
C8 C 0.23641(19) 0.6905(3) 0.06414(17) 0.0498(6) Uani 1 1 d . . .
C2 C 0.41649(19) 0.7563(3) 0.04055(17) 0.0498(6) Uani 1 1 d . . .
O15 O 0.16075(14) 0.7730(2) 0.06709(14) 0.0764(6) Uani 1 1 d . . .
C9 C 0.22743(18) 0.5177(3) 0.03784(16) 0.0462(6) Uani 1 1 d . . .
C14 C 0.1376(2) 0.4618(4) -0.0027(2) 0.0656(8) Uani 1 1 d . . .
H14 H 0.0859 0.5347 -0.0178 0.079 Uiso 1 1 calc R . .
C5 C 0.4552(2) 0.9063(3) 0.17795(18) 0.0573(7) Uani 1 1 d . . .
C19 C 0.4915(2) 0.5449(3) -0.24671(19) 0.0627(8) Uani 1 1 d . . .
H19 H 0.5491 0.6034 -0.2284 0.075 Uiso 1 1 calc R . .
C11 C 0.2894(2) 0.2448(4) 0.0430(2) 0.0686(8) Uani 1 1 d . . .
H11 H 0.3405 0.1713 0.0590 0.082 Uiso 1 1 calc R . .
C20 C 0.4870(3) 0.4666(4) -0.3252(2) 0.0854(11) Uani 1 1 d . . .
H20 H 0.5411 0.4714 -0.3593 0.102 Uiso 1 1 calc R . .
C23 C 0.3279(2) 0.4520(4) -0.2221(2) 0.0811(10) Uani 1 1 d . . .
H23 H 0.2739 0.4459 -0.1880 0.097 Uiso 1 1 calc R . .
C12 C 0.1996(3) 0.1911(4) 0.0034(2) 0.0850(10) Uani 1 1 d . . .
H12 H 0.1898 0.0811 -0.0073 0.102 Uiso 1 1 calc R . .
C6 C 0.5072(3) 0.9990(3) 0.2527(2) 0.0837(10) Uani 1 1 d . . .
H6A H 0.4600 1.0705 0.2764 0.126 Uiso 1 1 calc R . .
H6B H 0.5615 1.0611 0.2326 0.126 Uiso 1 1 calc R . .
H6C H 0.5334 0.9244 0.2965 0.126 Uiso 1 1 calc R . .
C7 C 0.2853(3) 0.8711(4) 0.2368(2) 0.0833(10) Uani 1 1 d . . .
H7A H 0.3215 0.8914 0.2920 0.125 Uiso 1 1 calc R . .
H7B H 0.2456 0.7746 0.2401 0.125 Uiso 1 1 calc R . .
H7C H 0.2420 0.9613 0.2213 0.125 Uiso 1 1 calc R . .
C22 C 0.3238(4) 0.3725(4) -0.3028(3) 0.1026(14) Uani 1 1 d . . .
H22 H 0.2670 0.3131 -0.3221 0.123 Uiso 1 1 calc R . .
C13 C 0.1237(3) 0.3000(4) -0.0208(2) 0.0891(11) Uani 1 1 d . . .
H13 H 0.0635 0.2640 -0.0492 0.107 Uiso 1 1 calc R . .
C21 C 0.4031(4) 0.3826(4) -0.3524(3) 0.1007(14) Uani 1 1 d . . .
H21 H 0.3995 0.3307 -0.4059 0.121 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 C5 1.710(3) . ?
S1 C2 1.721(3) . ?
C17 C16 1.187(4) . ?
C17 C18 1.444(4) . ?
C4 C5 1.369(4) . ?
C4 C3 1.427(3) . ?
C4 C7 1.498(4) . ?
C18 C23 1.380(4) . ?
C18 C19 1.382(4) . ?
C16 C2 1.422(4) . ?
C10 C11 1.375(4) . ?
C10 C9 1.385(3) . ?
C10 H10 0.9300 . ?
C3 C2 1.373(3) . ?
C3 C8 1.484(3) . ?
C8 O15 1.222(3) . ?
C8 C9 1.485(3) . ?
C9 C14 1.383(3) . ?
C14 C13 1.374(4) . ?
C14 H14 0.9300 . ?
C5 C6 1.506(4) . ?
C19 C20 1.374(4) . ?
C19 H19 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C20 C21 1.353(5) . ?
C20 H20 0.9300 . ?
C23 C22 1.409(5) . ?
C23 H23 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C22 C21 1.363(6) . ?
C22 H22 0.9300 . ?
C13 H13 0.9300 . ?
C21 H21 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
C5 S1 C2 92.44(13) . . ?
C16 C17 C18 176.3(3) . . ?
C5 C4 C3 112.2(2) . . ?
C5 C4 C7 123.9(3) . . ?
C3 C4 C7 123.9(3) . . ?
C23 C18 C19 118.6(3) . . ?
C23 C18 C17 120.2(3) . . ?
C19 C18 C17 121.2(2) . . ?
C17 C16 C2 177.9(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C2 C3 C4 112.9(2) . . ?
C2 C3 C8 123.7(2) . . ?
C4 C3 C8 123.4(2) . . ?
O15 C8 C3 119.7(2) . . ?
O15 C8 C9 119.9(2) . . ?
C3 C8 C9 120.3(2) . . ?
C3 C2 C16 127.5(2) . . ?
C3 C2 S1 110.8(2) . . ?
C16 C2 S1 121.7(2) . . ?
C14 C9 C10 118.7(2) . . ?
C14 C9 C8 119.4(2) . . ?
C10 C9 C8 121.7(2) . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C4 C5 C6 128.0(3) . . ?
C4 C5 S1 111.7(2) . . ?
C6 C5 S1 120.3(2) . . ?
C20 C19 C18 121.8(3) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C21 C20 C19 119.2(4) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C18 C23 C22 119.2(4) . . ?
C18 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C21 C22 C23 120.0(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C20 C21 C22 121.2(4) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?

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
C5 C4 C3 C2 -1.1(3) . . . . ?
C7 C4 C3 C2 -178.7(2) . . . . ?
C5 C4 C3 C8 -178.4(2) . . . . ?
C7 C4 C3 C8 4.0(4) . . . . ?
C2 C3 C8 O15 -128.4(3) . . . . ?
C4 C3 C8 O15 48.6(4) . . . . ?
C2 C3 C8 C9 54.4(3) . . . . ?
C4 C3 C8 C9 -128.6(3) . . . . ?
C4 C3 C2 C16 -177.7(2) . . . . ?
C8 C3 C2 C16 -0.4(4) . . . . ?
C4 C3 C2 S1 0.4(3) . . . . ?
C8 C3 C2 S1 177.63(18) . . . . ?
C5 S1 C2 C3 0.4(2) . . . . ?
C5 S1 C2 C16 178.5(2) . . . . ?
C11 C10 C9 C14 -2.2(4) . . . . ?
C11 C10 C9 C8 172.4(2) . . . . ?
O15 C8 C9 C14 15.5(4) . . . . ?
C3 C8 C9 C14 -167.3(2) . . . . ?
O15 C8 C9 C10 -159.0(3) . . . . ?
C3 C8 C9 C10 18.2(4) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
C8 C9 C14 C13 -174.1(3) . . . . ?
C3 C4 C5 C6 -177.9(2) . . . . ?
C7 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 S1 1.4(3) . . . . ?
C7 C4 C5 S1 179.0(2) . . . . ?
C2 S1 C5 C4 -1.0(2) . . . . ?
C2 S1 C5 C6 178.3(2) . . . . ?
C23 C18 C19 C20 0.0(4) . . . . ?
C17 C18 C19 C20 179.7(3) . . . . ?
C9 C10 C11 C12 1.7(4) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C19 C18 C23 C22 -0.2(4) . . . . ?
C17 C18 C23 C22 -179.8(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C18 C23 C22 C21 -0.2(5) . . . . ?
C9 C14 C13 C12 1.4(5) . . . . ?
C11 C12 C13 C14 -1.9(5) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
C23 C22 C21 C20 0.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.040
