# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_fxm-fx-st-bts
_database_code_depnum_ccdc_archive 'CCDC 1446714'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;
_audit_creation_date             2016-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_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_absolute_configuration rmad
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   5.7389(4)
_cell_length_b                   11.4338(8)
_cell_length_c                   22.2456(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1459.70(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3974
_cell_measurement_temperature    207(70)
_cell_measurement_theta_max      27.8320
_cell_measurement_theta_min      3.9260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.564
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      207(70)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00  100.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845   57.0000  -30.0000 109

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00  106.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845   77.0000  120.0000 121

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00  106.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845   77.0000    0.0000 121

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   90.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       25.5845 -178.0000 -180.0000 56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0224488000
_diffrn_orient_matrix_UB_12      0.0605683000
_diffrn_orient_matrix_UB_13      0.0037104000
_diffrn_orient_matrix_UB_21      -0.0296763000
_diffrn_orient_matrix_UB_22      0.0043008000
_diffrn_orient_matrix_UB_23      -0.0308901000
_diffrn_orient_matrix_UB_31      -0.1178777000
_diffrn_orient_matrix_UB_32      -0.0124706000
_diffrn_orient_matrix_UB_33      0.0070446000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2742
_reflns_number_total             2969
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 985 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1068
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00C(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00C), C00B(H00D), C00D(H00G), C00E(H00H), C00F(H00I),
 C00G(H00J), C00H(H00K), C00I(H00L), C00J(H00M), C00K(H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S -0.06107(13) 0.12095(6) 0.63953(3) 0.0334(2) Uani 1 1 d . . . . .
O002 O 0.3290(4) 0.40899(18) 0.78783(10) 0.0478(6) Uani 1 1 d . . . . .
C003 C 0.2843(5) 0.2405(2) 0.72861(12) 0.0283(6) Uani 1 1 d . . . . .
C004 C -0.0365(5) 0.3300(2) 0.58155(12) 0.0308(6) Uani 1 1 d . . . . .
C005 C 0.1038(5) 0.2544(2) 0.62416(12) 0.0288(6) Uani 1 1 d . . . . .
H005 H 0.2495 0.2326 0.6041 0.035 Uiso 1 1 calc R . . . .
C006 C 0.1639(5) 0.3164(2) 0.68283(12) 0.0308(6) Uani 1 1 d . . . . .
H00A H 0.2635 0.3826 0.6738 0.037 Uiso 1 1 calc R . . . .
H00B H 0.0214 0.3466 0.7004 0.037 Uiso 1 1 calc R . . . .
C007 C 0.2851(5) 0.1231(2) 0.72729(12) 0.0306(6) Uani 1 1 d . . . . .
H007 H 0.3687 0.0853 0.7574 0.037 Uiso 1 1 calc R . . . .
C008 C 0.5459(5) 0.2509(2) 0.82532(12) 0.0301(6) Uani 1 1 d . . . . .
C009 C 0.3835(5) 0.3061(2) 0.78056(12) 0.0315(6) Uani 1 1 d . . . . .
C00A C 0.7324(5) 0.1806(2) 0.80809(13) 0.0330(6) Uani 1 1 d . . . . .
H00C H 0.7522 0.1607 0.7679 0.040 Uiso 1 1 calc R . . . .
C00B C 0.0469(6) 0.3563(2) 0.52451(12) 0.0336(6) Uani 1 1 d . . . . .
H00D H 0.1884 0.3252 0.5119 0.040 Uiso 1 1 calc R . . . .
C00C C 0.1652(6) 0.0473(2) 0.68227(13) 0.0358(7) Uani 1 1 d . . . . .
H00E H 0.0965 -0.0189 0.7031 0.043 Uiso 1 1 calc R . . . .
H00F H 0.2806 0.0169 0.6545 0.043 Uiso 1 1 calc R . . . .
C00D C -0.2497(5) 0.3771(3) 0.59940(14) 0.0381(7) Uani 1 1 d . . . . .
H00G H -0.3081 0.3600 0.6374 0.046 Uiso 1 1 calc R . . . .
C00E C 0.8901(5) 0.1399(3) 0.85128(13) 0.0381(7) Uani 1 1 d . . . . .
H00H H 1.0163 0.0942 0.8396 0.046 Uiso 1 1 calc R . . . .
C00F C 0.5192(6) 0.2797(3) 0.88619(14) 0.0390(7) Uani 1 1 d . . . . .
H00I H 0.3966 0.3275 0.8981 0.047 Uiso 1 1 calc R . . . .
C00G C -0.0793(7) 0.4288(3) 0.48594(13) 0.0430(8) Uani 1 1 d . . . . .
H00J H -0.0216 0.4461 0.4479 0.052 Uiso 1 1 calc R . . . .
C00H C 0.8589(6) 0.1674(3) 0.91107(15) 0.0440(8) Uani 1 1 d . . . . .
H00K H 0.9622 0.1389 0.9398 0.053 Uiso 1 1 calc R . . . .
C00I C -0.3763(6) 0.4493(3) 0.56097(16) 0.0461(8) Uani 1 1 d . . . . .
H00L H -0.5182 0.4804 0.5733 0.055 Uiso 1 1 calc R . . . .
C00J C -0.2901(7) 0.4747(3) 0.50437(16) 0.0481(9) Uani 1 1 d . . . . .
H00M H -0.3744 0.5228 0.4786 0.058 Uiso 1 1 calc R . . . .
C00K C 0.6737(6) 0.2375(3) 0.92845(14) 0.0460(8) Uani 1 1 d . . . . .
H00N H 0.6535 0.2561 0.9688 0.055 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
S001 C005 1.828(3) . ?
S001 C00C 1.817(3) . ?
O002 C009 1.228(3) . ?
C003 C006 1.506(3) . ?
C003 C007 1.342(4) . ?
C003 C009 1.491(4) . ?
C004 C005 1.515(4) . ?
C004 C00B 1.389(4) . ?
C004 C00D 1.394(4) . ?
C005 H005 0.9800 . ?
C005 C006 1.524(4) . ?
C006 H00A 0.9700 . ?
C006 H00B 0.9700 . ?
C007 H007 0.9300 . ?
C007 C00C 1.493(4) . ?
C008 C009 1.502(4) . ?
C008 C00A 1.393(4) . ?
C008 C00F 1.402(4) . ?
C00A H00C 0.9300 . ?
C00A C00E 1.399(4) . ?
C00B H00D 0.9300 . ?
C00B C00G 1.396(4) . ?
C00C H00E 0.9700 . ?
C00C H00F 0.9700 . ?
C00D H00G 0.9300 . ?
C00D C00I 1.393(4) . ?
C00E H00H 0.9300 . ?
C00E C00H 1.378(4) . ?
C00F H00I 0.9300 . ?
C00F C00K 1.379(4) . ?
C00G H00J 0.9300 . ?
C00G C00J 1.381(5) . ?
C00H H00K 0.9300 . ?
C00H C00K 1.386(5) . ?
C00I H00L 0.9300 . ?
C00I C00J 1.384(5) . ?
C00J H00M 0.9300 . ?
C00K H00N 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
C00C S001 C005 96.62(13) . . ?
C007 C003 C006 124.3(3) . . ?
C007 C003 C009 121.3(3) . . ?
C009 C003 C006 114.2(2) . . ?
C00B C004 C005 120.8(3) . . ?
C00B C004 C00D 118.6(3) . . ?
C00D C004 C005 120.6(3) . . ?
S001 C005 H005 108.3 . . ?
C004 C005 S001 108.57(19) . . ?
C004 C005 H005 108.3 . . ?
C004 C005 C006 113.0(2) . . ?
C006 C005 S001 110.17(19) . . ?
C006 C005 H005 108.3 . . ?
C003 C006 C005 114.5(2) . . ?
C003 C006 H00A 108.6 . . ?
C003 C006 H00B 108.6 . . ?
C005 C006 H00A 108.6 . . ?
C005 C006 H00B 108.6 . . ?
H00A C006 H00B 107.6 . . ?
C003 C007 H007 116.8 . . ?
C003 C007 C00C 126.5(3) . . ?
C00C C007 H007 116.8 . . ?
C00A C008 C009 122.5(2) . . ?
C00A C008 C00F 119.0(3) . . ?
C00F C008 C009 118.3(3) . . ?
O002 C009 C003 119.1(3) . . ?
O002 C009 C008 118.2(2) . . ?
C003 C009 C008 122.6(2) . . ?
C008 C00A H00C 120.0 . . ?
C008 C00A C00E 120.0(3) . . ?
C00E C00A H00C 120.0 . . ?
C004 C00B H00D 119.6 . . ?
C004 C00B C00G 120.7(3) . . ?
C00G C00B H00D 119.6 . . ?
S001 C00C H00E 108.7 . . ?
S001 C00C H00F 108.7 . . ?
C007 C00C S001 114.27(19) . . ?
C007 C00C H00E 108.7 . . ?
C007 C00C H00F 108.7 . . ?
H00E C00C H00F 107.6 . . ?
C004 C00D H00G 119.6 . . ?
C00I C00D C004 120.8(3) . . ?
C00I C00D H00G 119.6 . . ?
C00A C00E H00H 119.9 . . ?
C00H C00E C00A 120.2(3) . . ?
C00H C00E H00H 119.9 . . ?
C008 C00F H00I 119.8 . . ?
C00K C00F C008 120.4(3) . . ?
C00K C00F H00I 119.8 . . ?
C00B C00G H00J 120.1 . . ?
C00J C00G C00B 119.9(3) . . ?
C00J C00G H00J 120.1 . . ?
C00E C00H H00K 120.0 . . ?
C00E C00H C00K 120.0(3) . . ?
C00K C00H H00K 120.0 . . ?
C00D C00I H00L 120.1 . . ?
C00J C00I C00D 119.7(3) . . ?
C00J C00I H00L 120.1 . . ?
C00G C00J C00I 120.3(3) . . ?
C00G C00J H00M 119.9 . . ?
C00I C00J H00M 119.9 . . ?
C00F C00K C00H 120.3(3) . . ?
C00F C00K H00N 119.8 . . ?
C00H C00K H00N 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
S001 C005 C006 C003 53.0(3) . . . . ?
C003 C007 C00C S001 -17.6(4) . . . . ?
C004 C005 C006 C003 174.7(2) . . . . ?
C004 C00B C00G C00J -0.3(4) . . . . ?
C004 C00D C00I C00J 0.1(4) . . . . ?
C005 S001 C00C C007 44.5(2) . . . . ?
C005 C004 C00B C00G -178.1(3) . . . . ?
C005 C004 C00D C00I 178.2(3) . . . . ?
C006 C003 C007 C00C -1.6(5) . . . . ?
C006 C003 C009 O002 12.0(4) . . . . ?
C006 C003 C009 C008 -168.9(2) . . . . ?
C007 C003 C006 C005 -17.8(4) . . . . ?
C007 C003 C009 O002 -161.7(3) . . . . ?
C007 C003 C009 C008 17.4(4) . . . . ?
C008 C00A C00E C00H 1.3(5) . . . . ?
C008 C00F C00K C00H 0.9(5) . . . . ?
C009 C003 C006 C005 168.7(2) . . . . ?
C009 C003 C007 C00C 171.5(3) . . . . ?
C009 C008 C00A C00E 174.4(3) . . . . ?
C009 C008 C00F C00K -175.7(3) . . . . ?
C00A C008 C009 O002 -135.6(3) . . . . ?
C00A C008 C009 C003 45.3(4) . . . . ?
C00A C008 C00F C00K -0.9(5) . . . . ?
C00A C00E C00H C00K -1.3(5) . . . . ?
C00B C004 C005 S001 -116.7(3) . . . . ?
C00B C004 C005 C006 120.7(3) . . . . ?
C00B C004 C00D C00I -0.3(4) . . . . ?
C00B C00G C00J C00I 0.2(5) . . . . ?
C00C S001 C005 C004 173.49(19) . . . . ?
C00C S001 C005 C006 -62.2(2) . . . . ?
C00D C004 C005 S001 64.8(3) . . . . ?
C00D C004 C005 C006 -57.7(4) . . . . ?
C00D C004 C00B C00G 0.4(4) . . . . ?
C00D C00I C00J C00G -0.1(5) . . . . ?
C00E C00H C00K C00F 0.3(5) . . . . ?
C00F C008 C009 O002 38.9(4) . . . . ?
C00F C008 C009 C003 -140.2(3) . . . . ?
C00F C008 C00A C00E -0.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-29
_olex2_submission_special_instructions 'No special instructions were received'
