# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_anzhy_0617
_database_code_depnum_ccdc_archive 'CCDC 1495452'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 O S'
_chemical_formula_sum            'C18 H16 O S'
_chemical_formula_weight         280.37
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   11.1348(9)
_cell_length_b                   10.8734(10)
_cell_length_c                   24.741(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2995.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    695
_cell_measurement_temperature    293.26(10)
_cell_measurement_theta_max      18.5780
_cell_measurement_theta_min      3.6550
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_unetI/netI     0.1408
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6738
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.26(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00  101.65   1.0500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   38.0000   60.0000 113

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   44.15   1.0500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108  -38.0000   90.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0476993000
_diffrn_orient_matrix_UB_12      0.0398776000
_diffrn_orient_matrix_UB_13      0.0073662000
_diffrn_orient_matrix_UB_21      0.0045071000
_diffrn_orient_matrix_UB_22      -0.0203346000
_diffrn_orient_matrix_UB_23      0.0271553000
_diffrn_orient_matrix_UB_31      0.0420142000
_diffrn_orient_matrix_UB_32      0.0474469000
_diffrn_orient_matrix_UB_33      0.0054519000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1023
_reflns_number_total             2946
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2039
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1889
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.33111(11) 0.05459(14) 0.34597(6) 0.0872(6) Uani 1 d . . .
O2 O -0.0034(3) -0.0121(3) 0.38708(12) 0.0654(9) Uani 1 d . . .
C3 C -0.0918(4) -0.1777(4) 0.33634(19) 0.0621(13) Uani 1 d . . .
C4 C 0.0110(5) -0.1009(4) 0.34812(19) 0.0620(13) Uani 1 d . . .
C5 C 0.1037(4) 0.0518(4) 0.39169(18) 0.0569(12) Uani 1 d . . .
C6 C 0.1057(4) 0.1485(4) 0.43175(19) 0.0590(12) Uani 1 d . . .
C7 C 0.1835(4) 0.0030(4) 0.35504(18) 0.0588(12) Uani 1 d . . .
C8 C -0.0861(5) -0.2694(5) 0.2979(2) 0.0751(15) Uani 1 d . . .
H8 H -0.0144 -0.2815 0.2794 0.090 Uiso 1 calc . . R
C9 C 0.1100(5) 0.3376(5) 0.5101(2) 0.0700(14) Uani 1 d . . .
C10 C 0.1969(4) 0.3287(5) 0.4711(2) 0.0815(16) Uani 1 d . . .
H10 H 0.2589 0.3859 0.4704 0.098 Uiso 1 calc . . R
C11 C 0.1228(5) -0.0931(4) 0.32808(19) 0.0710(14) Uani 1 d . . .
H11 H 0.1548 -0.1427 0.3010 0.085 Uiso 1 calc . . R
C12 C -0.2966(5) -0.2380(5) 0.3516(3) 0.0943(19) Uani 1 d . . .
H12 H -0.3686 -0.2265 0.3701 0.113 Uiso 1 calc . . R
C13 C 0.1134(5) 0.4396(4) 0.5517(2) 0.0921(17) Uani 1 d . . .
H13A H 0.1567 0.4121 0.5831 0.138 Uiso 1 calc . . GR
H13B H 0.0329 0.4612 0.5619 0.138 Uiso 1 calc . . GR
H13C H 0.1529 0.5102 0.5367 0.138 Uiso 1 calc . . GR
C14 C -0.1990(5) -0.1636(4) 0.3636(2) 0.0823(16) Uani 1 d . . .
H14 H -0.2059 -0.1036 0.3902 0.099 Uiso 1 calc . . R
C15 C -0.1824(6) -0.3432(5) 0.2861(2) 0.0912(18) Uani 1 d . . .
H15 H -0.1758 -0.4038 0.2597 0.109 Uiso 1 calc . . R
C16 C 0.0187(5) 0.1581(5) 0.4712(2) 0.0886(17) Uani 1 d . . .
H16 H -0.0431 0.1006 0.4724 0.106 Uiso 1 calc . . R
C17 C 0.1941(4) 0.2364(5) 0.4326(2) 0.0820(16) Uani 1 d . . .
H17 H 0.2541 0.2337 0.4065 0.098 Uiso 1 calc . . R
C18 C 0.0215(5) 0.2503(5) 0.5086(2) 0.0947(18) Uani 1 d . . .
H18 H -0.0394 0.2540 0.5343 0.114 Uiso 1 calc . . R
C19 C 0.3985(5) -0.0715(5) 0.3142(3) 0.129(2) Uani 1 d . . .
H19A H 0.3608 -0.0853 0.2798 0.194 Uiso 1 calc . . GR
H19B H 0.3891 -0.1432 0.3364 0.194 Uiso 1 calc . . GR
H19C H 0.4824 -0.0552 0.3089 0.194 Uiso 1 calc . . GR
C20 C -0.2886(6) -0.3274(5) 0.3134(3) 0.0941(19) Uani 1 d . . .
H20 H -0.3544 -0.3772 0.3058 0.113 Uiso 1 calc . . R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0756(10) 0.1036(12) 0.0825(11) -0.0089(10) 0.0088(8) -0.0068(8)
O2 0.071(2) 0.068(2) 0.058(2) -0.001(2) 0.0001(17) 0.0001(17)
C3 0.074(4) 0.061(3) 0.052(3) 0.005(3) -0.007(3) -0.005(3)
C4 0.078(4) 0.062(3) 0.045(3) 0.004(3) -0.005(3) 0.010(3)
C5 0.058(3) 0.070(3) 0.043(3) 0.010(3) -0.010(2) -0.006(3)
C6 0.066(3) 0.064(3) 0.046(3) 0.001(3) -0.009(3) -0.006(3)
C7 0.069(3) 0.062(3) 0.045(3) 0.008(3) 0.002(3) 0.002(2)
C8 0.095(4) 0.076(3) 0.055(3) -0.006(3) -0.013(3) -0.007(3)
C9 0.078(3) 0.079(4) 0.054(3) 0.002(3) -0.011(3) -0.004(3)
C10 0.074(4) 0.095(4) 0.075(4) -0.001(4) -0.005(3) -0.024(3)
C11 0.092(4) 0.070(3) 0.051(3) -0.005(3) -0.002(3) 0.000(3)
C12 0.086(4) 0.083(4) 0.115(5) -0.002(4) 0.003(4) -0.010(3)
C13 0.117(4) 0.089(4) 0.070(4) -0.022(4) -0.006(3) -0.008(3)
C14 0.087(4) 0.067(3) 0.093(4) -0.014(3) 0.001(3) -0.010(3)
C15 0.115(5) 0.082(4) 0.076(4) -0.013(4) -0.028(4) -0.006(4)
C16 0.092(4) 0.085(4) 0.088(4) -0.020(4) 0.025(4) -0.024(3)
C17 0.084(4) 0.094(4) 0.068(4) -0.021(4) 0.005(3) -0.015(3)
C18 0.098(4) 0.096(4) 0.090(4) -0.021(4) 0.030(4) -0.018(3)
C19 0.101(4) 0.124(5) 0.163(6) -0.024(5) 0.056(4) 0.001(4)
C20 0.094(5) 0.084(4) 0.104(5) 0.000(4) -0.032(4) -0.016(3)

_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 C7 1.751(4) . ?
S1 C19 1.749(5) . ?
O2 C4 1.374(5) . ?
O2 C5 1.385(5) . ?
C3 C4 1.448(6) . ?
C3 C8 1.379(6) . ?
C3 C14 1.379(6) . ?
C4 C11 1.342(6) . ?
C5 C6 1.446(6) . ?
C5 C7 1.376(6) . ?
C6 C16 1.380(6) . ?
C6 C17 1.371(6) . ?
C7 C11 1.412(6) . ?
C8 H8 0.9300 . ?
C8 C15 1.371(6) . ?
C9 C10 1.370(6) . ?
C9 C13 1.514(6) . ?
C9 C18 1.368(6) . ?
C10 H10 0.9300 . ?
C10 C17 1.384(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C14 1.387(6) . ?
C12 C20 1.360(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C20 1.373(7) . ?
C16 H16 0.9300 . ?
C16 C18 1.365(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 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
C19 S1 C7 102.0(2) . . ?
C4 O2 C5 108.0(4) . . ?
C8 C3 C4 121.3(5) . . ?
C8 C3 C14 117.2(4) . . ?
C14 C3 C4 121.5(5) . . ?
O2 C4 C3 117.0(4) . . ?
C11 C4 O2 108.9(4) . . ?
C11 C4 C3 134.1(5) . . ?
O2 C5 C6 115.7(4) . . ?
C7 C5 O2 108.0(4) . . ?
C7 C5 C6 136.3(4) . . ?
C16 C6 C5 122.0(5) . . ?
C17 C6 C5 121.9(5) . . ?
C17 C6 C16 116.1(5) . . ?
C5 C7 S1 124.5(4) . . ?
C5 C7 C11 106.7(4) . . ?
C11 C7 S1 128.8(4) . . ?
C3 C8 H8 118.9 . . ?
C15 C8 C3 122.3(5) . . ?
C15 C8 H8 118.9 . . ?
C10 C9 C13 120.8(5) . . ?
C18 C9 C10 116.2(5) . . ?
C18 C9 C13 123.0(5) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C17 121.3(5) . . ?
C17 C10 H10 119.4 . . ?
C4 C11 C7 108.4(5) . . ?
C4 C11 H11 125.8 . . ?
C7 C11 H11 125.8 . . ?
C14 C12 H12 119.5 . . ?
C20 C12 H12 119.5 . . ?
C20 C12 C14 120.9(5) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 C12 120.6(5) . . ?
C3 C14 H14 119.7 . . ?
C12 C14 H14 119.7 . . ?
C8 C15 H15 120.2 . . ?
C8 C15 C20 119.7(6) . . ?
C20 C15 H15 120.2 . . ?
C6 C16 H16 119.4 . . ?
C18 C16 C6 121.3(5) . . ?
C18 C16 H16 119.4 . . ?
C6 C17 C10 122.2(5) . . ?
C6 C17 H17 118.9 . . ?
C10 C17 H17 118.9 . . ?
C9 C18 H18 118.5 . . ?
C16 C18 C9 123.0(5) . . ?
C16 C18 H18 118.5 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 C15 119.2(5) . . ?
C12 C20 H20 120.4 . . ?
C15 C20 H20 120.4 . . ?

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
S1 C7 C11 C4 179.8(3) . . . . ?
O2 C4 C11 C7 0.5(5) . . . . ?
O2 C5 C6 C16 14.8(6) . . . . ?
O2 C5 C6 C17 -165.1(4) . . . . ?
O2 C5 C7 S1 179.8(3) . . . . ?
O2 C5 C7 C11 -0.4(5) . . . . ?
C3 C4 C11 C7 178.6(5) . . . . ?
C3 C8 C15 C20 -0.6(8) . . . . ?
C4 O2 C5 C6 -179.1(3) . . . . ?
C4 O2 C5 C7 0.7(4) . . . . ?
C4 C3 C8 C15 -180.0(4) . . . . ?
C4 C3 C14 C12 179.9(5) . . . . ?
C5 O2 C4 C3 -179.2(3) . . . . ?
C5 O2 C4 C11 -0.7(5) . . . . ?
C5 C6 C16 C18 -179.7(5) . . . . ?
C5 C6 C17 C10 -179.6(4) . . . . ?
C5 C7 C11 C4 0.0(5) . . . . ?
C6 C5 C7 S1 -0.4(7) . . . . ?
C6 C5 C7 C11 179.4(5) . . . . ?
C6 C16 C18 C9 -0.8(9) . . . . ?
C7 C5 C6 C16 -165.0(5) . . . . ?
C7 C5 C6 C17 15.2(8) . . . . ?
C8 C3 C4 O2 -180.0(4) . . . . ?
C8 C3 C4 C11 2.0(8) . . . . ?
C8 C3 C14 C12 -1.0(7) . . . . ?
C8 C15 C20 C12 0.3(8) . . . . ?
C9 C10 C17 C6 -0.7(8) . . . . ?
C10 C9 C18 C16 0.7(8) . . . . ?
C13 C9 C10 C17 -179.5(4) . . . . ?
C13 C9 C18 C16 -179.8(5) . . . . ?
C14 C3 C4 O2 -0.9(6) . . . . ?
C14 C3 C4 C11 -178.9(5) . . . . ?
C14 C3 C8 C15 0.9(7) . . . . ?
C14 C12 C20 C15 -0.4(8) . . . . ?
C16 C6 C17 C10 0.6(8) . . . . ?
C17 C6 C16 C18 0.1(8) . . . . ?
C18 C9 C10 C17 0.0(7) . . . . ?
C19 S1 C7 C5 160.0(4) . . . . ?
C19 S1 C7 C11 -19.8(5) . . . . ?
C20 C12 C14 C3 0.8(8) . . . . ?

_olex2_date_sample_data_collection 2016-06-17
_olex2_submission_special_instructions 'No special instructions were received'
