# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_yamamoto0826
_database_code_depnum_ccdc_archive 'CCDC 1420832'
_audit_update_record             
;
2015-08-27 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H8 O2 S'
_chemical_formula_moiety         'C12 H8 O2 S'
_chemical_formula_weight         216.25
_chemical_melting_point          385-389
_chemical_absolute_configuration S

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.1577(10)
_cell_length_b                   7.3665(13)
_cell_length_c                   11.253(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.935(5)
_cell_angle_gamma                90.0000
_cell_volume                     510.15(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3629
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.672
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224.00
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_T_max  0.949

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4978
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2133
_reflns_number_gt                1660
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1171
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2133
_refine_ls_number_parameters     140
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0629P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  878 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.13(12)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.91205(12) 0.29607(11) 0.55555(6) 0.0546(3) Uani 1.0 2 d . . .
O1 O 0.3980(3) 0.3112(3) 0.22442(15) 0.0432(5) Uani 1.0 2 d . . .
O2 O 0.0747(3) 0.2673(5) 0.13282(18) 0.0611(7) Uani 1.0 2 d . . .
C1 C 0.2505(5) 0.2051(5) 0.1644(3) 0.0446(7) Uani 1.0 2 d . . .
C2 C 0.6041(4) 0.2125(4) 0.2430(3) 0.0359(6) Uani 1.0 2 d . . .
C3 C 0.5520(5) 0.0252(4) 0.1964(3) 0.0356(6) Uani 1.0 2 d . . .
C4 C 0.6799(5) -0.1282(4) 0.1909(3) 0.0429(7) Uani 1.0 2 d . . .
C5 C 0.5915(6) -0.2816(5) 0.1372(3) 0.0519(8) Uani 1.0 2 d . . .
C6 C 0.3807(6) -0.2806(6) 0.0885(3) 0.0561(9) Uani 1.0 2 d . . .
C7 C 0.2537(5) -0.1277(5) 0.0929(3) 0.0507(8) Uani 1.0 2 d . . .
C8 C 0.3429(5) 0.0253(5) 0.1481(3) 0.0403(7) Uani 1.0 2 d . . .
C9 C 0.6795(4) 0.2229(4) 0.3705(3) 0.0366(6) Uani 1.0 2 d . . .
C10 C 0.8638(5) 0.3114(5) 0.4063(3) 0.0431(6) Uani 1.0 2 d . . .
C11 C 0.6878(6) 0.1676(5) 0.5726(3) 0.0521(8) Uani 1.0 2 d . . .
C12 C 0.5776(5) 0.1374(5) 0.4672(3) 0.0461(8) Uani 1.0 2 d . . .
H1 H 0.702(4) 0.268(4) 0.194(3) 0.024(6) Uiso 1.0 2 d . . .
H2 H 0.8245 -0.1285 0.2232 0.0514 Uiso 1.0 2 calc R . .
H3 H 0.6761 -0.3892 0.1334 0.0623 Uiso 1.0 2 calc R . .
H4 H 0.3239 -0.3874 0.0518 0.0673 Uiso 1.0 2 calc R . .
H5 H 0.1100 -0.1265 0.0594 0.0609 Uiso 1.0 2 calc R . .
H6 H 0.9552 0.3746 0.3540 0.0517 Uiso 1.0 2 calc R . .
H7 H 0.6436 0.1218 0.6469 0.0626 Uiso 1.0 2 calc R . .
H8 H 0.4482 0.0675 0.4594 0.0553 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C10 1.699(3) yes . .
S1 C11 1.690(4) yes . .
O1 C1 1.361(4) yes . .
O1 C2 1.471(4) yes . .
O2 C1 1.217(4) yes . .
C1 C8 1.456(5) yes . .
C2 C3 1.507(4) yes . .
C2 C9 1.494(4) yes . .
C3 C4 1.380(5) yes . .
C3 C8 1.380(4) yes . .
C4 C5 1.385(5) yes . .
C5 C6 1.391(5) yes . .
C6 C7 1.373(6) yes . .
C7 C8 1.391(5) yes . .
C9 C10 1.358(4) yes . .
C9 C12 1.422(4) yes . .
C11 C12 1.365(5) yes . .
C2 H1 0.93(3) no . .
C4 H2 0.950 no . .
C5 H3 0.950 no . .
C6 H4 0.950 no . .
C7 H5 0.950 no . .
C10 H6 0.950 no . .
C11 H7 0.950 no . .
C12 H8 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C10 S1 C11 91.91(15) yes . . .
C1 O1 C2 110.2(3) yes . . .
O1 C1 O2 120.1(4) yes . . .
O1 C1 C8 109.1(3) yes . . .
O2 C1 C8 130.8(3) yes . . .
O1 C2 C3 103.3(2) yes . . .
O1 C2 C9 110.5(2) yes . . .
C3 C2 C9 115.9(3) yes . . .
C2 C3 C4 130.5(3) yes . . .
C2 C3 C8 108.8(3) yes . . .
C4 C3 C8 120.6(3) yes . . .
C3 C4 C5 118.1(3) yes . . .
C4 C5 C6 121.0(4) yes . . .
C5 C6 C7 121.0(4) yes . . .
C6 C7 C8 117.6(3) yes . . .
C1 C8 C3 108.3(3) yes . . .
C1 C8 C7 130.0(3) yes . . .
C3 C8 C7 121.6(3) yes . . .
C2 C9 C10 122.6(3) yes . . .
C2 C9 C12 125.5(3) yes . . .
C10 C9 C12 111.8(3) yes . . .
S1 C10 C9 112.2(3) yes . . .
S1 C11 C12 112.1(3) yes . . .
C9 C12 C11 111.9(3) yes . . .
O1 C2 H1 105.9(16) no . . .
C3 C2 H1 109.5(17) no . . .
C9 C2 H1 111.1(15) no . . .
C3 C4 H2 120.951 no . . .
C5 C4 H2 120.949 no . . .
C4 C5 H3 119.490 no . . .
C6 C5 H3 119.482 no . . .
C5 C6 H4 119.505 no . . .
C7 C6 H4 119.501 no . . .
C6 C7 H5 121.185 no . . .
C8 C7 H5 121.185 no . . .
S1 C10 H6 123.889 no . . .
C9 C10 H6 123.886 no . . .
S1 C11 H7 123.944 no . . .
C12 C11 H7 123.933 no . . .
C9 C12 H8 124.025 no . . .
C11 C12 H8 124.032 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C10 S1 C11 C12 -0.3(3) no . . . .
C11 S1 C10 C9 0.8(3) no . . . .
C1 O1 C2 C3 -5.5(3) no . . . .
C1 O1 C2 C9 -130.1(2) no . . . .
C2 O1 C1 O2 -174.7(3) no . . . .
C2 O1 C1 C8 4.7(3) no . . . .
O1 C1 C8 C3 -1.7(3) no . . . .
O1 C1 C8 C7 179.7(3) no . . . .
O2 C1 C8 C3 177.5(3) no . . . .
O2 C1 C8 C7 -1.0(5) no . . . .
O1 C2 C3 C4 -179.3(3) no . . . .
O1 C2 C3 C8 4.3(3) no . . . .
O1 C2 C9 C10 -114.3(3) no . . . .
O1 C2 C9 C12 68.7(4) no . . . .
C3 C2 C9 C10 128.7(3) no . . . .
C3 C2 C9 C12 -48.3(4) no . . . .
C9 C2 C3 C4 -58.3(4) no . . . .
C9 C2 C3 C8 125.3(2) no . . . .
C2 C3 C4 C5 -176.7(3) no . . . .
C2 C3 C8 C1 -1.8(3) no . . . .
C2 C3 C8 C7 176.9(2) no . . . .
C4 C3 C8 C1 -178.6(3) no . . . .
C4 C3 C8 C7 0.1(4) no . . . .
C8 C3 C4 C5 -0.7(4) no . . . .
C3 C4 C5 C6 0.8(5) no . . . .
C4 C5 C6 C7 -0.3(5) no . . . .
C5 C6 C7 C8 -0.3(5) no . . . .
C6 C7 C8 C1 178.8(3) no . . . .
C6 C7 C8 C3 0.4(4) no . . . .
C2 C9 C10 S1 -178.6(3) no . . . .
C2 C9 C12 C11 178.3(3) no . . . .
C10 C9 C12 C11 1.0(4) no . . . .
C12 C9 C10 S1 -1.2(4) no . . . .
S1 C11 C12 C9 -0.4(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C10 3.467(3) no . .
O1 C12 3.182(4) no . .
O2 C2 3.472(3) no . .
O2 C3 3.491(4) no . .
O2 C7 3.149(5) no . .
C1 C9 3.459(4) no . .
C3 C6 2.752(5) no . .
C3 C12 3.157(4) no . .
C4 C7 2.812(5) no . .
C4 C9 3.282(4) no . .
C5 C8 2.735(5) no . .
C8 C9 3.511(4) no . .
O1 C5 3.385(5) no . 1_565
O1 C6 3.373(5) no . 1_565
O1 C11 3.531(4) no . 2_656
O2 C2 3.216(4) no . 1_455
O2 C7 3.285(4) no . 2_555
O2 C10 3.396(4) no . 1_455
C1 C5 3.563(4) no . 2_655
C2 O2 3.216(4) no . 1_655
C3 C6 3.548(4) no . 2_655
C5 O1 3.385(5) no . 1_545
C5 C1 3.563(4) no . 2_645
C5 C8 3.547(5) no . 2_645
C6 O1 3.373(5) no . 1_545
C6 C3 3.548(4) no . 2_645
C6 C8 3.512(5) no . 2_645
C7 O2 3.285(4) no . 2_545
C8 C5 3.547(5) no . 2_655
C8 C6 3.512(5) no . 2_655
C10 O2 3.396(4) no . 1_655
C11 O1 3.531(4) no . 2_646
S1 H8 3.4576 no . .
O1 H8 3.2021 no . .
O2 H5 3.0257 no . .
C1 H1 2.83(3) no . .
C1 H5 2.8355 no . .
C2 H2 2.8677 no . .
C2 H6 2.7345 no . .
C2 H8 2.8544 no . .
C3 H3 3.2312 no . .
C3 H5 3.2782 no . .
C3 H8 3.0648 no . .
C4 H1 2.92(3) no . .
C4 H4 3.2671 no . .
C5 H5 3.2691 no . .
C6 H2 3.2769 no . .
C7 H3 3.2560 no . .
C8 H1 2.88(3) no . .
C8 H2 3.2591 no . .
C8 H4 3.2284 no . .
C8 H8 3.5542 no . .
C9 H2 3.2161 no . .
C9 H7 3.2139 no . .
C10 H1 2.58(3) no . .
C10 H7 3.3716 no . .
C10 H8 3.1994 no . .
C11 H6 3.3708 no . .
C12 H1 3.34(3) no . .
C12 H6 3.2067 no . .
H1 H2 3.0329 no . .
H1 H6 2.4675 no . .
H2 H3 2.3411 no . .
H3 H4 2.3266 no . .
H4 H5 2.3332 no . .
H7 H8 2.4270 no . .
S1 H2 2.9778 no . 2_756
S1 H6 3.3597 no . 2_746
S1 H8 2.9870 no . 2_656
O1 H3 2.9949 no . 1_565
O1 H4 2.9756 no . 1_565
O1 H6 3.1700 no . 1_455
O1 H7 2.7241 no . 2_656
O2 H1 2.42(3) no . 1_455
O2 H2 3.4664 no . 1_455
O2 H3 3.5258 no . 1_465
O2 H4 3.1226 no . 1_565
O2 H4 3.3604 no . 2_555
O2 H5 2.5339 no . 2_555
O2 H6 2.7360 no . 1_455
C1 H1 3.43(3) no . 1_455
C1 H3 3.4667 no . 2_655
C1 H4 3.2952 no . 1_565
C1 H5 3.5257 no . 2_555
C1 H6 3.1116 no . 1_455
C2 H3 3.2192 no . 1_565
C2 H4 3.4413 no . 2_655
C3 H4 2.9898 no . 2_655
C4 H4 3.2560 no . 2_655
C4 H5 3.0771 no . 1_655
C4 H7 3.3071 no . 2_646
C5 H1 3.44(3) no . 1_545
C5 H5 3.5291 no . 1_655
C5 H7 2.9569 no . 2_646
C6 H1 3.22(3) no . 2_645
C6 H7 3.0710 no . 2_646
C7 H1 3.34(3) no . 2_645
C7 H2 3.0652 no . 1_455
C7 H3 3.1362 no . 2_655
C7 H4 3.5829 no . 2_655
C7 H7 3.5003 no . 2_646
C8 H2 3.5171 no . 1_455
C8 H3 3.2285 no . 2_655
C8 H4 3.1614 no . 2_655
C9 H7 3.5506 no . 2_656
C9 H8 3.2913 no . 2_656
C10 H8 3.1194 no . 2_656
C11 H6 3.1701 no . 2_746
C11 H8 3.0805 no . 2_656
C12 H8 3.2798 no . 2_656
H1 O2 2.42(3) no . 1_655
H1 C1 3.43(3) no . 1_655
H1 C5 3.44(3) no . 1_565
H1 C6 3.22(3) no . 2_655
H1 C7 3.34(3) no . 2_655
H1 H3 2.6179 no . 1_565
H1 H4 2.9939 no . 2_655
H1 H5 3.2092 no . 2_655
H2 S1 2.9778 no . 2_746
H2 O2 3.4664 no . 1_655
H2 C7 3.0652 no . 1_655
H2 C8 3.5171 no . 1_655
H2 H5 2.5894 no . 1_655
H3 O1 2.9949 no . 1_545
H3 O2 3.5258 no . 1_645
H3 C1 3.4667 no . 2_645
H3 C2 3.2192 no . 1_545
H3 C7 3.1362 no . 2_645
H3 C8 3.2285 no . 2_645
H3 H1 2.6179 no . 1_545
H3 H5 3.4248 no . 1_655
H3 H5 3.1134 no . 2_645
H3 H6 3.4433 no . 1_545
H3 H7 3.2124 no . 2_646
H4 O1 2.9756 no . 1_545
H4 O2 3.1226 no . 1_545
H4 O2 3.3604 no . 2_545
H4 C1 3.2952 no . 1_545
H4 C2 3.4413 no . 2_645
H4 C3 2.9898 no . 2_645
H4 C4 3.2560 no . 2_645
H4 C7 3.5829 no . 2_645
H4 C8 3.1614 no . 2_645
H4 H1 2.9939 no . 2_645
H4 H5 3.4027 no . 2_545
H4 H7 3.3905 no . 2_646
H5 O2 2.5339 no . 2_545
H5 C1 3.5257 no . 2_545
H5 C4 3.0771 no . 1_455
H5 C5 3.5291 no . 1_455
H5 H1 3.2092 no . 2_645
H5 H2 2.5894 no . 1_455
H5 H3 3.4248 no . 1_455
H5 H3 3.1134 no . 2_655
H5 H4 3.4027 no . 2_555
H6 S1 3.3597 no . 2_756
H6 O1 3.1700 no . 1_655
H6 O2 2.7360 no . 1_655
H6 C1 3.1116 no . 1_655
H6 C11 3.1701 no . 2_756
H6 H3 3.4433 no . 1_565
H6 H7 3.0691 no . 2_756
H6 H8 3.5989 no . 2_656
H7 O1 2.7241 no . 2_646
H7 C4 3.3071 no . 2_656
H7 C5 2.9569 no . 2_656
H7 C6 3.0710 no . 2_656
H7 C7 3.5003 no . 2_656
H7 C9 3.5506 no . 2_646
H7 H3 3.2124 no . 2_656
H7 H4 3.3905 no . 2_656
H7 H6 3.0691 no . 2_746
H7 H8 3.5337 no . 2_656
H8 S1 2.9870 no . 2_646
H8 C9 3.2913 no . 2_646
H8 C10 3.1194 no . 2_646
H8 C11 3.0805 no . 2_646
H8 C12 3.2798 no . 2_646
H8 H6 3.5989 no . 2_646
H8 H7 3.5337 no . 2_646

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================

_chemical_name_systematic        
(S)-3-(thiophen-3-yl)-1,3-dihydro-2-benzofuran-1-one
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethylether/hexane'
