# 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_Compound3k
_database_code_depnum_ccdc_archive 'CCDC 1494571'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Ph-CH3)-S-[Ph(OCH3)3]
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 O3 S'
_chemical_formula_sum            'C16 H18 O3 S'
_chemical_formula_weight         290.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9478(5)
_cell_length_b                   9.1969(5)
_cell_length_c                   11.8012(10)
_cell_angle_alpha                82.206(6)
_cell_angle_beta                 81.643(7)
_cell_angle_gamma                75.220(6)
_cell_volume                     717.54(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2032
_cell_measurement_theta_min      3.7730
_cell_measurement_theta_max      73.5020

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_T_max  0.7915
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.  
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4482
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         69.98
_reflns_number_total             2692
_reflns_number_gt                2226
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0501P)²+0.0995P] 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         2692
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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
S1 S 0.43447(6) 0.71095(5) 1.04268(4) 0.01961(14) Uani 1 1 d . . .
O1 O 0.95897(18) 0.93408(15) 0.75707(11) 0.0201(3) Uani 1 1 d . . .
O2 O 0.83089(18) 0.85511(13) 0.57610(10) 0.0179(3) Uani 1 1 d . . .
O3 O 0.53312(18) 0.71622(14) 0.60189(10) 0.0182(3) Uani 1 1 d . . .
C1 C 0.6228(3) 0.6831(2) 1.13577(15) 0.0169(4) Uani 1 1 d . . .
C2 C 0.8068(3) 0.5786(2) 1.11504(15) 0.0175(4) Uani 1 1 d . . .
H2A H 0.8320 0.5222 1.0505 0.021 Uiso 1 1 calc R . .
C3 C 0.9520(3) 0.5577(2) 1.18873(15) 0.0185(4) Uani 1 1 d . . .
H3A H 1.0778 0.4887 1.1730 0.022 Uiso 1 1 calc R . .
C4 C 0.9160(3) 0.6368(2) 1.28582(15) 0.0182(4) Uani 1 1 d . . .
C5 C 0.7299(3) 0.7361(2) 1.30762(16) 0.0186(4) Uani 1 1 d . . .
H5A H 0.7009 0.7873 1.3751 0.022 Uiso 1 1 calc R . .
C6 C 0.5852(3) 0.7616(2) 1.23204(15) 0.0177(4) Uani 1 1 d . . .
H6A H 0.4610 0.8328 1.2465 0.021 Uiso 1 1 calc R . .
C7 C 1.0772(3) 0.6149(2) 1.36394(17) 0.0240(4) Uani 1 1 d . . .
H7A H 1.0271 0.6785 1.4272 0.036 Uiso 1 1 calc R . .
H7B H 1.1953 0.6434 1.3200 0.036 Uiso 1 1 calc R . .
H7C H 1.1139 0.5085 1.3953 0.036 Uiso 1 1 calc R . .
C8 C 0.5628(3) 0.7529(2) 0.90534(15) 0.0164(4) Uani 1 1 d . . .
C9 C 0.7143(3) 0.8304(2) 0.89143(15) 0.0172(4) Uani 1 1 d . . .
H9A H 0.7549 0.8606 0.9563 0.021 Uiso 1 1 calc R . .
C10 C 0.8048(3) 0.86279(19) 0.78110(15) 0.0161(4) Uani 1 1 d . . .
C11 C 0.7405(3) 0.8240(2) 0.68514(15) 0.0159(4) Uani 1 1 d . . .
C12 C 0.5851(3) 0.7491(2) 0.70046(15) 0.0160(4) Uani 1 1 d . . .
C13 C 0.4997(3) 0.7097(2) 0.81128(15) 0.0170(4) Uani 1 1 d . . .
H13A H 0.3996 0.6539 0.8223 0.020 Uiso 1 1 calc R . .
C14 C 1.0346(3) 0.9707(2) 0.85301(16) 0.0213(4) Uani 1 1 d . . .
H14A H 0.9296 1.0442 0.8943 0.032 Uiso 1 1 calc R . .
H14B H 1.1499 1.0143 0.8256 0.032 Uiso 1 1 calc R . .
H14C H 1.0762 0.8789 0.9050 0.032 Uiso 1 1 calc R . .
C15 C 0.7627(3) 1.0096(2) 0.53006(16) 0.0212(4) Uani 1 1 d . . .
H15A H 0.6159 1.0375 0.5382 0.032 Uiso 1 1 calc R . .
H15B H 0.8144 1.0214 0.4484 0.032 Uiso 1 1 calc R . .
H15C H 0.8113 1.0753 0.5721 0.032 Uiso 1 1 calc R . .
C16 C 0.3726(3) 0.6415(2) 0.61329(16) 0.0218(4) Uani 1 1 d . . .
H16A H 0.4097 0.5433 0.6588 0.033 Uiso 1 1 calc R . .
H16B H 0.3469 0.6264 0.5368 0.033 Uiso 1 1 calc R . .
H16C H 0.2514 0.7039 0.6521 0.033 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 C1 1.7760(18) . ?
S1 C8 1.7768(18) . ?
O1 C10 1.370(2) . ?
O1 C14 1.428(2) . ?
O2 C11 1.374(2) . ?
O2 C15 1.435(2) . ?
O3 C12 1.359(2) . ?
O3 C16 1.434(2) . ?
C1 C6 1.386(3) . ?
C1 C2 1.401(2) . ?
C2 C3 1.387(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(3) . ?
C4 C7 1.510(2) . ?
C5 C6 1.394(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.390(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.396(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.396(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C1 S1 C8 102.71(8) . . ?
C10 O1 C14 116.90(14) . . ?
C11 O2 C15 113.02(13) . . ?
C12 O3 C16 117.09(14) . . ?
C6 C1 C2 119.53(17) . . ?
C6 C1 S1 119.79(14) . . ?
C2 C1 S1 120.65(14) . . ?
C3 C2 C1 119.99(17) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 120.90(17) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 118.47(16) . . ?
C5 C4 C7 121.32(17) . . ?
C3 C4 C7 120.21(17) . . ?
C4 C5 C6 121.04(17) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 120.00(17) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
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 . . ?
C13 C8 C9 121.29(16) . . ?
C13 C8 S1 116.71(13) . . ?
C9 C8 S1 121.95(14) . . ?
C10 C9 C8 118.86(16) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
O1 C10 C9 124.14(16) . . ?
O1 C10 C11 115.01(15) . . ?
C9 C10 C11 120.85(16) . . ?
O2 C11 C10 120.84(15) . . ?
O2 C11 C12 119.62(16) . . ?
C10 C11 C12 119.53(16) . . ?
O3 C12 C13 124.81(16) . . ?
O3 C12 C11 115.14(15) . . ?
C13 C12 C11 120.02(16) . . ?
C8 C13 C12 119.35(16) . . ?
C8 C13 H13A 120.3 . . ?
C12 C13 H13A 120.3 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 S1 C1 C6 127.82(14) . . . . ?
C8 S1 C1 C2 -54.35(16) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
S1 C1 C2 C3 -179.76(13) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C7 -178.85(16) . . . . ?
C3 C4 C5 C6 -2.8(3) . . . . ?
C7 C4 C5 C6 176.72(16) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
S1 C1 C6 C5 177.68(13) . . . . ?
C4 C5 C6 C1 2.6(3) . . . . ?
C1 S1 C8 C13 149.45(14) . . . . ?
C1 S1 C8 C9 -32.95(17) . . . . ?
C13 C8 C9 C10 -0.9(3) . . . . ?
S1 C8 C9 C10 -178.37(13) . . . . ?
C14 O1 C10 C9 2.7(2) . . . . ?
C14 O1 C10 C11 -177.70(15) . . . . ?
C8 C9 C10 O1 -177.93(16) . . . . ?
C8 C9 C10 C11 2.5(3) . . . . ?
C15 O2 C11 C10 -79.8(2) . . . . ?
C15 O2 C11 C12 101.70(19) . . . . ?
O1 C10 C11 O2 0.8(2) . . . . ?
C9 C10 C11 O2 -179.58(16) . . . . ?
O1 C10 C11 C12 179.29(15) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C16 O3 C12 C13 2.9(2) . . . . ?
C16 O3 C12 C11 -179.10(15) . . . . ?
O2 C11 C12 O3 -1.5(2) . . . . ?
C10 C11 C12 O3 179.97(15) . . . . ?
O2 C11 C12 C13 176.52(15) . . . . ?
C10 C11 C12 C13 -2.0(3) . . . . ?
C9 C8 C13 C12 -2.1(3) . . . . ?
S1 C8 C13 C12 175.47(13) . . . . ?
O3 C12 C13 C8 -178.57(16) . . . . ?
C11 C12 C13 C8 3.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        69.98
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_Compound3j
_database_code_depnum_ccdc_archive 'CCDC 1494572'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Ph-CH3)-S-(Ph-(OCH3)2)
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 O2 S'
_chemical_formula_sum            'C15 H16 O2 S'
_chemical_formula_weight         260.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   7.68603(16)
_cell_length_b                   23.9176(4)
_cell_length_c                   7.76261(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.053(3)
_cell_angle_gamma                90.00
_cell_volume                     1331.76(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5424
_cell_measurement_theta_min      3.6850
_cell_measurement_theta_max      73.5140

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5553
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.  
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8328
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         69.98
_reflns_number_total             2513
_reflns_number_gt                2348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0418P)²+0.5327P] 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         2513
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_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
S1 S 0.78479(4) 0.624768(13) 0.66078(4) 0.01741(11) Uani 1 1 d . . .
O1 O 0.78451(13) 0.60701(4) 1.03468(12) 0.0207(2) Uani 1 1 d . . .
O2 O 0.74528(14) 0.40890(4) 1.01458(13) 0.0222(2) Uani 1 1 d . . .
C1 C 0.56680(17) 0.65825(5) 0.61586(16) 0.0155(3) Uani 1 1 d . . .
C2 C 0.54684(18) 0.71194(5) 0.54073(17) 0.0185(3) Uani 1 1 d . . .
H2A H 0.6470 0.7285 0.5148 0.022 Uiso 1 1 calc R . .
C3 C 0.38150(19) 0.74126(5) 0.50370(17) 0.0195(3) Uani 1 1 d . . .
H3A H 0.3696 0.7777 0.4520 0.023 Uiso 1 1 calc R . .
C4 C 0.23280(18) 0.71803(5) 0.54127(17) 0.0177(3) Uani 1 1 d . . .
C5 C 0.25398(18) 0.66410(5) 0.61441(17) 0.0178(3) Uani 1 1 d . . .
H5A H 0.1531 0.6474 0.6388 0.021 Uiso 1 1 calc R . .
C6 C 0.41845(18) 0.63429(5) 0.65248(17) 0.0166(3) Uani 1 1 d . . .
H6A H 0.4299 0.5977 0.7032 0.020 Uiso 1 1 calc R . .
C7 C 0.05617(19) 0.75053(6) 0.50989(19) 0.0225(3) Uani 1 1 d . . .
H7A H 0.0657 0.7873 0.4582 0.034 Uiso 1 1 calc R . .
H7B H 0.0378 0.7554 0.6276 0.034 Uiso 1 1 calc R . .
H7C H -0.0499 0.7301 0.4235 0.034 Uiso 1 1 calc R . .
C8 C 0.76172(17) 0.56036(5) 0.76138(18) 0.0162(3) Uani 1 1 d . . .
C9 C 0.76979(17) 0.55731(5) 0.94532(17) 0.0162(3) Uani 1 1 d . . .
C10 C 0.76147(18) 0.50593(5) 1.02400(17) 0.0174(3) Uani 1 1 d . . .
H10A H 0.7645 0.5039 1.1473 0.021 Uiso 1 1 calc R . .
C11 C 0.74855(17) 0.45700(5) 0.92174(18) 0.0173(3) Uani 1 1 d . . .
C12 C 0.73886(18) 0.45910(5) 0.74009(18) 0.0197(3) Uani 1 1 d . . .
H12A H 0.7284 0.4258 0.6704 0.024 Uiso 1 1 calc R . .
C13 C 0.74487(18) 0.51118(5) 0.66216(17) 0.0185(3) Uani 1 1 d . . .
H13A H 0.7372 0.5131 0.5374 0.022 Uiso 1 1 calc R . .
C14 C 0.7832(2) 0.60571(6) 1.21832(18) 0.0233(3) Uani 1 1 d . . .
H14A H 0.7945 0.6439 1.2671 0.035 Uiso 1 1 calc R . .
H14B H 0.8882 0.5832 1.2969 0.035 Uiso 1 1 calc R . .
H14C H 0.6660 0.5892 1.2169 0.035 Uiso 1 1 calc R . .
C15 C 0.7526(2) 0.35739(5) 0.9237(2) 0.0240(3) Uani 1 1 d . . .
H15A H 0.7492 0.3260 1.0035 0.036 Uiso 1 1 calc R . .
H15B H 0.8682 0.3558 0.8977 0.036 Uiso 1 1 calc R . .
H15C H 0.6454 0.3551 0.8076 0.036 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 C8 1.7646(13) . ?
S1 C1 1.7750(13) . ?
O1 C9 1.3605(15) . ?
O1 C14 1.4295(15) . ?
O2 C11 1.3626(15) . ?
O2 C15 1.4307(16) . ?
C1 C6 1.3936(18) . ?
C1 C2 1.3958(18) . ?
C2 C3 1.3882(19) . ?
C3 C4 1.3926(19) . ?
C4 C5 1.3950(18) . ?
C4 C7 1.5063(18) . ?
C5 C6 1.3876(18) . ?
C8 C13 1.3863(18) . ?
C8 C9 1.4086(18) . ?
C9 C10 1.3840(18) . ?
C10 C11 1.3974(18) . ?
C11 C12 1.3860(19) . ?
C12 C13 1.3928(19) . ?

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
C8 S1 C1 104.06(6) . . ?
C9 O1 C14 117.41(10) . . ?
C11 O2 C15 117.05(10) . . ?
C6 C1 C2 119.23(12) . . ?
C6 C1 S1 123.93(10) . . ?
C2 C1 S1 116.84(9) . . ?
C3 C2 C1 120.42(12) . . ?
C2 C3 C4 120.94(12) . . ?
C3 C4 C5 118.01(12) . . ?
C3 C4 C7 121.33(12) . . ?
C5 C4 C7 120.63(12) . . ?
C6 C5 C4 121.73(12) . . ?
C5 C6 C1 119.66(12) . . ?
C13 C8 C9 118.72(11) . . ?
C13 C8 S1 119.93(10) . . ?
C9 C8 S1 121.26(10) . . ?
O1 C9 C10 124.02(11) . . ?
O1 C9 C8 115.91(11) . . ?
C10 C9 C8 120.08(11) . . ?
C9 C10 C11 119.87(12) . . ?
O2 C11 C12 124.35(11) . . ?
O2 C11 C10 114.69(11) . . ?
C12 C11 C10 120.96(12) . . ?
C11 C12 C13 118.44(12) . . ?
C8 C13 C12 121.91(12) . . ?

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 S1 C1 C6 -1.70(12) . . . . ?
C8 S1 C1 C2 177.77(9) . . . . ?
C6 C1 C2 C3 0.31(18) . . . . ?
S1 C1 C2 C3 -179.18(10) . . . . ?
C1 C2 C3 C4 0.31(19) . . . . ?
C2 C3 C4 C5 -1.00(19) . . . . ?
C2 C3 C4 C7 177.11(12) . . . . ?
C3 C4 C5 C6 1.12(18) . . . . ?
C7 C4 C5 C6 -177.00(12) . . . . ?
C4 C5 C6 C1 -0.53(19) . . . . ?
C2 C1 C6 C5 -0.20(18) . . . . ?
S1 C1 C6 C5 179.26(9) . . . . ?
C1 S1 C8 C13 107.96(11) . . . . ?
C1 S1 C8 C9 -75.41(11) . . . . ?
C14 O1 C9 C10 -2.76(18) . . . . ?
C14 O1 C9 C8 176.80(11) . . . . ?
C13 C8 C9 O1 -179.39(11) . . . . ?
S1 C8 C9 O1 3.94(16) . . . . ?
C13 C8 C9 C10 0.19(19) . . . . ?
S1 C8 C9 C10 -176.48(10) . . . . ?
O1 C9 C10 C11 -179.26(11) . . . . ?
C8 C9 C10 C11 1.20(19) . . . . ?
C15 O2 C11 C12 7.02(18) . . . . ?
C15 O2 C11 C10 -173.41(11) . . . . ?
C9 C10 C11 O2 178.67(11) . . . . ?
C9 C10 C11 C12 -1.75(19) . . . . ?
O2 C11 C12 C13 -179.58(12) . . . . ?
C10 C11 C12 C13 0.87(19) . . . . ?
C9 C8 C13 C12 -1.08(19) . . . . ?
S1 C8 C13 C12 175.63(10) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        69.98
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_Compound3m
_database_code_depnum_ccdc_archive 'CCDC 1494573'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Ph-CH3)-S-(Ph-CN)
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N S'
_chemical_formula_sum            'C14 H11 N S'
_chemical_formula_weight         225.30

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'
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   'P 21/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                   5.7042(3)
_cell_length_b                   25.743(2)
_cell_length_c                   7.8069(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.590(5)
_cell_angle_gamma                90.00
_cell_volume                     1142.70(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2351
_cell_measurement_theta_min      3.6480
_cell_measurement_theta_max      29.0310

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9283
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.  
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4848
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2240
_reflns_number_gt                1962
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0301P)²+1.0963P] 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         2240
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
S1 S 0.55230(8) 0.726933(19) 0.48229(7) 0.01687(15) Uani 1 1 d . . .
N1 N -0.1282(3) 0.50942(7) 0.7182(3) 0.0301(5) Uani 1 1 d . . .
C1 C 0.4036(3) 0.78500(7) 0.5330(2) 0.0144(4) Uani 1 1 d . . .
C2 C 0.1797(3) 0.79717(7) 0.4581(2) 0.0156(4) Uani 1 1 d . . .
H2A H 0.0939 0.7724 0.3879 0.019 Uiso 1 1 calc R . .
C3 C 0.0836(3) 0.84555(8) 0.4867(3) 0.0171(4) Uani 1 1 d . . .
H3A H -0.0706 0.8532 0.4382 0.020 Uiso 1 1 calc R . .
C4 C 0.2077(3) 0.88335(8) 0.5851(3) 0.0176(4) Uani 1 1 d . . .
C5 C 0.4305(3) 0.87041(8) 0.6600(3) 0.0189(4) Uani 1 1 d . . .
H5A H 0.5175 0.8953 0.7286 0.023 Uiso 1 1 calc R . .
C6 C 0.5270(3) 0.82166(8) 0.6359(2) 0.0168(4) Uani 1 1 d . . .
H6A H 0.6775 0.8133 0.6898 0.020 Uiso 1 1 calc R . .
C7 C 0.1048(4) 0.93662(8) 0.6058(3) 0.0268(5) Uani 1 1 d . . .
H7A H 0.2151 0.9579 0.6783 0.040 Uiso 1 1 calc R . .
H7B H -0.0439 0.9336 0.6598 0.040 Uiso 1 1 calc R . .
H7C H 0.0760 0.9530 0.4927 0.040 Uiso 1 1 calc R . .
C8 C 0.3751(3) 0.67544(7) 0.5472(2) 0.0138(4) Uani 1 1 d . . .
C9 C 0.4527(3) 0.62543(8) 0.5111(3) 0.0170(4) Uani 1 1 d . . .
H9A H 0.5920 0.6211 0.4537 0.020 Uiso 1 1 calc R . .
C10 C 0.3291(3) 0.58233(8) 0.5578(3) 0.0184(4) Uani 1 1 d . . .
H10A H 0.3842 0.5484 0.5343 0.022 Uiso 1 1 calc R . .
C11 C 0.1217(3) 0.58884(8) 0.6403(3) 0.0167(4) Uani 1 1 d . . .
C12 C 0.0447(3) 0.63866(7) 0.6772(2) 0.0158(4) Uani 1 1 d . . .
H12A H -0.0949 0.6430 0.7343 0.019 Uiso 1 1 calc R . .
C13 C 0.1694(3) 0.68185(7) 0.6313(2) 0.0154(4) Uani 1 1 d . . .
H13A H 0.1158 0.7157 0.6569 0.018 Uiso 1 1 calc R . .
C14 C -0.0153(3) 0.54444(8) 0.6842(3) 0.0211(4) Uani 1 1 d . . .


_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 C8 1.7656(19) . ?
S1 C1 1.7788(19) . ?
N1 C14 1.151(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.397(3) . ?
C2 C3 1.386(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(3) . ?
C4 C7 1.506(3) . ?
C5 C6 1.389(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.397(3) . ?
C8 C13 1.400(3) . ?
C9 C10 1.379(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.402(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.393(3) . ?
C11 C14 1.441(3) . ?
C12 C13 1.382(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?

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
C8 S1 C1 105.84(9) . . ?
C6 C1 C2 119.48(18) . . ?
C6 C1 S1 118.01(14) . . ?
C2 C1 S1 122.12(15) . . ?
C3 C2 C1 119.63(17) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 121.66(17) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 117.94(18) . . ?
C5 C4 C7 121.48(18) . . ?
C3 C4 C7 120.57(18) . . ?
C6 C5 C4 121.06(18) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C1 120.18(17) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
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 . . ?
C9 C8 C13 119.62(17) . . ?
C9 C8 S1 115.85(14) . . ?
C13 C8 S1 124.53(15) . . ?
C10 C9 C8 120.73(18) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 119.57(18) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 119.77(18) . . ?
C12 C11 C14 119.68(18) . . ?
C10 C11 C14 120.54(18) . . ?
C13 C12 C11 120.64(18) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C8 119.66(18) . . ?
C12 C13 H13A 120.2 . . ?
C8 C13 H13A 120.2 . . ?
N1 C14 C11 178.8(2) . . ?

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 S1 C1 C6 125.17(15) . . . . ?
C8 S1 C1 C2 -62.07(18) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
S1 C1 C2 C3 -172.49(15) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C7 176.48(19) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C7 C4 C5 C6 -178.04(19) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
S1 C1 C6 C5 171.25(15) . . . . ?
C1 S1 C8 C9 176.78(14) . . . . ?
C1 S1 C8 C13 -3.82(18) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
S1 C8 C9 C10 179.27(15) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C9 C10 C11 C14 177.53(18) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C14 C11 C12 C13 -177.98(18) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
S1 C8 C13 C12 -179.67(14) . . . . ?
C12 C11 C14 N1 44(12) . . . . ?
C10 C11 C14 N1 -135(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_Compound3q
_database_code_depnum_ccdc_archive 'CCDC 1494574'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Ph-CH3)-S-(PhCOCH3)
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 O S'
_chemical_formula_sum            'C15 H14 O S'
_chemical_formula_weight         242.32

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   'P 21/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                   5.7958(3)
_cell_length_b                   25.4544(12)
_cell_length_c                   8.3123(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.626(4)
_cell_angle_gamma                90.00
_cell_volume                     1223.84(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3011
_cell_measurement_theta_min      3.6030
_cell_measurement_theta_max      29.0450

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9088
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5356
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2393
_reflns_number_gt                2047
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0354P)²+0.4817P] 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         2393
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
S1 S -0.02610(7) 0.229207(17) 0.60236(6) 0.02509(15) Uani 1 1 d . . .
O1 O 0.30015(19) -0.00821(4) 0.35762(14) 0.0250(3) Uani 1 1 d . . .
C1 C 0.1366(3) 0.28500(6) 0.54876(19) 0.0196(4) Uani 1 1 d . . .
C2 C 0.3511(3) 0.29565(7) 0.6278(2) 0.0218(4) Uani 1 1 d . . .
H2A H 0.4155 0.2720 0.7069 0.026 Uiso 1 1 calc R . .
C3 C 0.4695(3) 0.34068(7) 0.59051(19) 0.0210(4) Uani 1 1 d . . .
H3A H 0.6169 0.3473 0.6432 0.025 Uiso 1 1 calc R . .
C4 C 0.3776(3) 0.37660(6) 0.47742(19) 0.0192(3) Uani 1 1 d . . .
C5 C 0.1623(3) 0.36578(6) 0.40058(19) 0.0206(4) Uani 1 1 d . . .
H5A H 0.0963 0.3899 0.3234 0.025 Uiso 1 1 calc R . .
C6 C 0.0426(3) 0.32022(6) 0.43516(19) 0.0204(4) Uani 1 1 d . . .
H6A H -0.1034 0.3132 0.3811 0.024 Uiso 1 1 calc R . .
C7 C 0.5102(3) 0.42584(7) 0.4436(2) 0.0251(4) Uani 1 1 d . . .
H7A H 0.4226 0.4467 0.3617 0.038 Uiso 1 1 calc R . .
H7B H 0.6605 0.4164 0.4042 0.038 Uiso 1 1 calc R . .
H7C H 0.5337 0.4464 0.5429 0.038 Uiso 1 1 calc R . .
C8 C 0.1265(3) 0.17482(6) 0.52958(18) 0.0179(3) Uani 1 1 d . . .
C9 C 0.0234(3) 0.12611(7) 0.55285(19) 0.0205(4) Uani 1 1 d . . .
H9A H -0.1144 0.1241 0.6087 0.025 Uiso 1 1 calc R . .
C10 C 0.1194(3) 0.08090(6) 0.49560(19) 0.0204(4) Uani 1 1 d . . .
H10A H 0.0484 0.0480 0.5138 0.024 Uiso 1 1 calc R . .
C11 C 0.3204(3) 0.08280(6) 0.41090(18) 0.0174(3) Uani 1 1 d . . .
C12 C 0.4264(3) 0.13140(6) 0.39178(18) 0.0177(3) Uani 1 1 d . . .
H12A H 0.5655 0.1332 0.3375 0.021 Uiso 1 1 calc R . .
C13 C 0.3323(3) 0.17726(6) 0.45062(19) 0.0195(3) Uani 1 1 d . . .
H13A H 0.4073 0.2100 0.4373 0.023 Uiso 1 1 calc R . .
C14 C 0.4036(3) 0.03304(6) 0.33919(19) 0.0192(4) Uani 1 1 d . . .
C15 C 0.6099(3) 0.03435(7) 0.2386(2) 0.0259(4) Uani 1 1 d . . .
H15A H 0.6423 -0.0012 0.2008 0.039 Uiso 1 1 calc R . .
H15B H 0.7443 0.0476 0.3038 0.039 Uiso 1 1 calc R . .
H15C H 0.5777 0.0575 0.1457 0.039 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 C8 1.7700(16) . ?
S1 C1 1.7771(16) . ?
O1 C14 1.2234(19) . ?
C1 C6 1.388(2) . ?
C1 C2 1.395(2) . ?
C2 C3 1.381(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.393(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.393(2) . ?
C4 C7 1.506(2) . ?
C5 C6 1.391(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.395(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.376(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.399(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.395(2) . ?
C11 C14 1.493(2) . ?
C12 C13 1.390(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.502(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C8 S1 C1 104.76(7) . . ?
C6 C1 C2 119.63(15) . . ?
C6 C1 S1 119.66(12) . . ?
C2 C1 S1 120.55(13) . . ?
C3 C2 C1 119.74(15) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 121.47(15) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 118.23(15) . . ?
C5 C4 C7 122.13(15) . . ?
C3 C4 C7 119.63(14) . . ?
C6 C5 C4 120.95(15) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C1 C6 C5 119.98(15) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
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 . . ?
C9 C8 C13 119.36(15) . . ?
C9 C8 S1 114.82(11) . . ?
C13 C8 S1 125.81(13) . . ?
C10 C9 C8 120.58(14) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C11 120.86(15) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 118.32(15) . . ?
C12 C11 C14 123.46(14) . . ?
C10 C11 C14 118.15(14) . . ?
C13 C12 C11 121.29(14) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C12 C13 C8 119.53(15) . . ?
C12 C13 H13A 120.2 . . ?
C8 C13 H13A 120.2 . . ?
O1 C14 C11 120.31(14) . . ?
O1 C14 C15 120.17(15) . . ?
C11 C14 C15 119.48(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 S1 C1 C6 113.11(13) . . . . ?
C8 S1 C1 C2 -71.35(14) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
S1 C1 C2 C3 -176.55(12) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C2 C3 C4 C7 178.47(15) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C7 C4 C5 C6 -179.39(14) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
S1 C1 C6 C5 175.67(11) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C1 S1 C8 C9 -177.50(12) . . . . ?
C1 S1 C8 C13 1.13(17) . . . . ?
C13 C8 C9 C10 -1.5(2) . . . . ?
S1 C8 C9 C10 177.21(12) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C10 C11 C12 2.6(2) . . . . ?
C9 C10 C11 C14 -174.54(14) . . . . ?
C10 C11 C12 C13 -1.9(2) . . . . ?
C14 C11 C12 C13 175.08(14) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?
C9 C8 C13 C12 2.2(2) . . . . ?
S1 C8 C13 C12 -176.37(12) . . . . ?
C12 C11 C14 O1 -178.49(15) . . . . ?
C10 C11 C14 O1 -1.5(2) . . . . ?
C12 C11 C14 C15 -0.9(2) . . . . ?
C10 C11 C14 C15 176.11(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_Compound3r
_database_code_depnum_ccdc_archive 'CCDC 1494575'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Ph-CH3)-S-(PhCOOCH3)
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 O2 S'
_chemical_formula_sum            'C15 H14 O2 S'
_chemical_formula_weight         258.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   5.6110(3)
_cell_length_b                   25.6833(13)
_cell_length_c                   8.9910(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.982(4)
_cell_angle_gamma                90.00
_cell_volume                     1279.79(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1796
_cell_measurement_theta_min      5.2720
_cell_measurement_theta_max      71.9550

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.7809
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4586
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.27
_diffrn_reflns_theta_max         70.93
_reflns_number_total             2415
_reflns_number_gt                1925
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0382P)²+2.9498P] 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         2415
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_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
S1 S 0.42789(16) 0.25905(3) 0.62197(10) 0.0287(3) Uani 1 1 d . . .
O1 O 0.7685(5) 0.49228(9) 0.3767(3) 0.0312(6) Uani 1 1 d . . .
O2 O 1.0452(4) 0.43937(9) 0.3001(3) 0.0279(6) Uani 1 1 d . . .
C1 C 0.5837(6) 0.20477(13) 0.5617(4) 0.0241(7) Uani 1 1 d . . .
C2 C 0.8071(7) 0.18994(14) 0.6410(4) 0.0267(8) Uani 1 1 d . . .
H2A H 0.8762 0.2088 0.7280 0.032 Uiso 1 1 calc R . .
C3 C 0.9274(7) 0.14791(13) 0.5930(4) 0.0262(8) Uani 1 1 d . . .
H3A H 1.0804 0.1385 0.6471 0.031 Uiso 1 1 calc R . .
C4 C 0.8306(6) 0.11894(13) 0.4671(4) 0.0250(7) Uani 1 1 d . . .
C5 C 0.6063(7) 0.13377(14) 0.3898(4) 0.0273(8) Uani 1 1 d . . .
H5A H 0.5359 0.1143 0.3042 0.033 Uiso 1 1 calc R . .
C6 C 0.4830(6) 0.17655(14) 0.4352(4) 0.0258(7) Uani 1 1 d . . .
H6A H 0.3312 0.1864 0.3803 0.031 Uiso 1 1 calc R . .
C7 C 0.9688(7) 0.07333(14) 0.4176(4) 0.0321(8) Uani 1 1 d . . .
H7A H 1.1208 0.0692 0.4868 0.048 Uiso 1 1 calc R . .
H7B H 1.0031 0.0796 0.3155 0.048 Uiso 1 1 calc R . .
H7C H 0.8720 0.0416 0.4183 0.048 Uiso 1 1 calc R . .
C8 C 0.5734(6) 0.31267(13) 0.5518(3) 0.0215(7) Uani 1 1 d . . .
C9 C 0.4760(6) 0.36171(14) 0.5708(4) 0.0241(7) Uani 1 1 d . . .
H9A H 0.3428 0.3649 0.6238 0.029 Uiso 1 1 calc R . .
C10 C 0.5697(6) 0.40568(13) 0.5140(4) 0.0235(7) Uani 1 1 d . . .
H10A H 0.4990 0.4387 0.5259 0.028 Uiso 1 1 calc R . .
C11 C 0.7693(6) 0.40165(13) 0.4386(4) 0.0213(7) Uani 1 1 d . . .
C12 C 0.8702(6) 0.35283(13) 0.4226(4) 0.0221(7) Uani 1 1 d . . .
H12A H 1.0069 0.3499 0.3727 0.027 Uiso 1 1 calc R . .
C13 C 0.7746(6) 0.30849(13) 0.4783(4) 0.0224(7) Uani 1 1 d . . .
H13A H 0.8453 0.2754 0.4666 0.027 Uiso 1 1 calc R . .
C14 C 0.8569(6) 0.44939(13) 0.3715(4) 0.0236(7) Uani 1 1 d . . .
C15 C 1.1433(7) 0.48357(14) 0.2323(4) 0.0300(8) Uani 1 1 d . . .
H15A H 1.2791 0.4723 0.1835 0.045 Uiso 1 1 calc R . .
H15B H 1.1994 0.5094 0.3101 0.045 Uiso 1 1 calc R . .
H15C H 1.0182 0.4991 0.1570 0.045 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 C8 1.767(3) . ?
S1 C1 1.775(4) . ?
O1 C14 1.212(4) . ?
O2 C14 1.344(4) . ?
O2 C15 1.439(4) . ?
C1 C6 1.392(5) . ?
C1 C2 1.395(5) . ?
C2 C3 1.378(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(5) . ?
C4 C7 1.510(5) . ?
C5 C6 1.393(5) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.394(5) . ?
C8 C13 1.399(5) . ?
C9 C10 1.377(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.400(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.393(5) . ?
C11 C14 1.484(5) . ?
C12 C13 1.386(5) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C8 S1 C1 103.08(16) . . ?
C14 O2 C15 115.6(3) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 S1 120.1(3) . . ?
C2 C1 S1 120.3(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 C7 120.1(3) . . ?
C5 C4 C7 122.1(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
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 . . ?
C9 C8 C13 119.2(3) . . ?
C9 C8 S1 116.7(3) . . ?
C13 C8 S1 124.1(3) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 C14 122.4(3) . . ?
C10 C11 C14 118.5(3) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13A 120.2 . . ?
C8 C13 H13A 120.2 . . ?
O1 C14 O2 123.3(3) . . ?
O1 C14 C11 124.9(3) . . ?
O2 C14 C11 111.8(3) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 S1 C1 C6 -100.4(3) . . . . ?
C8 S1 C1 C2 79.9(3) . . . . ?
C6 C1 C2 C3 0.6(5) . . . . ?
S1 C1 C2 C3 -179.7(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 C7 179.7(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C7 C4 C5 C6 -178.8(3) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
S1 C1 C6 C5 -179.5(3) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C1 S1 C8 C9 174.8(3) . . . . ?
C1 S1 C8 C13 -4.4(3) . . . . ?
C13 C8 C9 C10 2.2(5) . . . . ?
S1 C8 C9 C10 -177.0(3) . . . . ?
C8 C9 C10 C11 -1.4(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C9 C10 C11 C14 176.6(3) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C14 C11 C12 C13 -175.8(3) . . . . ?
C11 C12 C13 C8 0.0(5) . . . . ?
C9 C8 C13 C12 -1.5(5) . . . . ?
S1 C8 C13 C12 177.7(2) . . . . ?
C15 O2 C14 O1 1.8(5) . . . . ?
C15 O2 C14 C11 -179.6(3) . . . . ?
C12 C11 C14 O1 176.6(3) . . . . ?
C10 C11 C14 O1 0.1(5) . . . . ?
C12 C11 C14 O2 -2.0(5) . . . . ?
C10 C11 C14 O2 -178.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        70.93
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_Compound4n
_database_code_depnum_ccdc_archive 'CCDC 1494576'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Ph-CN)-S-(PhOCH3)
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N O S'
_chemical_formula_sum            'C14 H11 N O S'
_chemical_formula_weight         241.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   5.67633(18)
_cell_length_b                   26.8781(8)
_cell_length_c                   7.7875(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.042(3)
_cell_angle_gamma                90.00
_cell_volume                     1183.54(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2597
_cell_measurement_theta_min      5.9100
_cell_measurement_theta_max      73.1010

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    2.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6120
_exptl_absorpt_correction_T_max  0.7418
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4295
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         5.94
_diffrn_reflns_theta_max         69.99
_reflns_number_total             2215
_reflns_number_gt                2056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0518P)²+0.3186P] 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         2215
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
S1 S 0.98535(6) 0.727733(13) -0.08450(4) 0.01822(14) Uani 1 1 d . . .
O1 O 0.55172(19) 0.92160(4) 0.05991(14) 0.0241(3) Uani 1 1 d . . .
C1 C 0.8132(2) 0.67870(5) -0.01193(16) 0.0152(3) Uani 1 1 d . . .
C2 C 0.6092(2) 0.68504(5) 0.07342(17) 0.0164(3) Uani 1 1 d . . .
H2A H 0.5540 0.7176 0.0960 0.020 Uiso 1 1 calc R . .
C3 C 0.4876(2) 0.64394(5) 0.12503(18) 0.0171(3) Uani 1 1 d . . .
H3A H 0.3484 0.6483 0.1828 0.021 Uiso 1 1 calc R . .
C4 C 0.5678(3) 0.59599(5) 0.09287(18) 0.0177(3) Uani 1 1 d . . .
C5 C 0.7723(3) 0.58939(5) 0.00681(19) 0.0211(3) Uani 1 1 d . . .
H5A H 0.8278 0.5569 -0.0153 0.025 Uiso 1 1 calc R . .
C6 C 0.8922(3) 0.63060(5) -0.04542(18) 0.0190(3) Uani 1 1 d . . .
H6A H 1.0300 0.6263 -0.1048 0.023 Uiso 1 1 calc R . .
C7 C 0.4357(3) 0.55407(6) 0.14703(19) 0.0225(3) Uani 1 1 d . . .
N1 N 0.3242(3) 0.52138(5) 0.19056(19) 0.0316(3) Uani 1 1 d . . .
C8 C 0.8422(2) 0.78328(5) -0.02678(17) 0.0162(3) Uani 1 1 d . . .
C9 C 0.9727(2) 0.81721(6) 0.07661(17) 0.0184(3) Uani 1 1 d . . .
H9A H 1.1250 0.8081 0.1273 0.022 Uiso 1 1 calc R . .
C10 C 0.8843(3) 0.86440(6) 0.10740(18) 0.0197(3) Uani 1 1 d . . .
H10A H 0.9773 0.8876 0.1758 0.024 Uiso 1 1 calc R . .
C11 C 0.6586(3) 0.87724(5) 0.03704(17) 0.0182(3) Uani 1 1 d . . .
C12 C 0.5249(2) 0.84286(5) -0.06540(17) 0.0177(3) Uani 1 1 d . . .
H12A H 0.3702 0.8514 -0.1125 0.021 Uiso 1 1 calc R . .
C13 C 0.6164(2) 0.79656(5) -0.09861(17) 0.0175(3) Uani 1 1 d . . .
H13A H 0.5258 0.7737 -0.1703 0.021 Uiso 1 1 calc R . .
C14 C 0.6902(3) 0.95969(6) 0.1493(2) 0.0285(4) Uani 1 1 d . . .
H14A H 0.5936 0.9897 0.1576 0.043 Uiso 1 1 calc R . .
H14B H 0.8274 0.9674 0.0860 0.043 Uiso 1 1 calc R . .
H14C H 0.7442 0.9480 0.2653 0.043 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 C1 1.7630(14) . ?
S1 C8 1.7763(15) . ?
O1 C11 1.3566(17) . ?
O1 C14 1.4332(18) . ?
C1 C2 1.3954(19) . ?
C1 C6 1.4006(19) . ?
C2 C3 1.381(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.397(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.402(2) . ?
C4 C7 1.437(2) . ?
C5 C6 1.380(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 N1 1.151(2) . ?
C8 C9 1.387(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.392(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.400(2) . ?
C12 C13 1.381(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C1 S1 C8 105.57(7) . . ?
C11 O1 C14 117.34(11) . . ?
C2 C1 C6 119.62(13) . . ?
C2 C1 S1 124.62(11) . . ?
C6 C1 S1 115.77(10) . . ?
C3 C2 C1 119.86(13) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.45(13) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 119.95(13) . . ?
C3 C4 C7 118.96(13) . . ?
C5 C4 C7 121.08(13) . . ?
C6 C5 C4 119.33(13) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C1 120.79(13) . . ?
C5 C6 H6A 119.6 . . ?
C1 C6 H6A 119.6 . . ?
N1 C7 C4 177.98(16) . . ?
C9 C8 C13 119.21(13) . . ?
C9 C8 S1 117.82(11) . . ?
C13 C8 S1 122.46(11) . . ?
C8 C9 C10 121.11(13) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C11 C10 C9 119.42(13) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
O1 C11 C10 124.95(13) . . ?
O1 C11 C12 115.41(12) . . ?
C10 C11 C12 119.64(13) . . ?
C13 C12 C11 120.51(13) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C8 120.07(13) . . ?
C12 C13 H13A 120.0 . . ?
C8 C13 H13A 120.0 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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 S1 C1 C2 -0.36(14) . . . . ?
C8 S1 C1 C6 179.38(10) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
S1 C1 C2 C3 -179.91(10) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 C3 C4 C7 -179.46(13) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C7 C4 C5 C6 179.02(13) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
S1 C1 C6 C5 179.46(11) . . . . ?
C1 S1 C8 C9 122.92(11) . . . . ?
C1 S1 C8 C13 -65.33(13) . . . . ?
C13 C8 C9 C10 -1.1(2) . . . . ?
S1 C8 C9 C10 170.92(11) . . . . ?
C8 C9 C10 C11 1.8(2) . . . . ?
C14 O1 C11 C10 6.3(2) . . . . ?
C14 O1 C11 C12 -173.91(13) . . . . ?
C9 C10 C11 O1 178.91(13) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
O1 C11 C12 C13 179.52(12) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C8 1.4(2) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
S1 C8 C13 C12 -172.10(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_Compound5a
_database_code_depnum_ccdc_archive 'CCDC 1494577'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2016-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Ph-CN)-S-S-(Ph-CN)
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 N2 S2'
_chemical_formula_sum            'C14 H8 N2 S2'
_chemical_formula_weight         268.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8232(4)
_cell_length_b                   11.6428(5)
_cell_length_c                   14.5818(7)
_cell_angle_alpha                84.863(4)
_cell_angle_beta                 83.654(4)
_cell_angle_gamma                73.557(4)
_cell_volume                     1263.68(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4813
_cell_measurement_theta_min      3.9320
_cell_measurement_theta_max      72.9700

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    3.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5001
_exptl_absorpt_correction_T_max  0.6681
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,Version 1.171.36.28 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8569
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         69.99
_reflns_number_total             4710
_reflns_number_gt                4073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0901P)²+5.6639P] 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         4710
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2166
_refine_ls_wR_factor_gt          0.2121
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
S1 S 0.45901(16) 0.81825(11) 0.94515(8) 0.0298(3) Uani 1 1 d . . .
S2 S 0.48042(15) 0.64333(11) 0.92853(8) 0.0293(3) Uani 1 1 d . . .
S3 S 0.59607(15) 0.34027(11) 0.58604(8) 0.0279(3) Uani 1 1 d . . .
S4 S 0.73911(16) 0.17044(11) 0.55852(8) 0.0280(3) Uani 1 1 d . . .
N1 N 0.2875(6) 1.1396(4) 0.5093(3) 0.0329(10) Uani 1 1 d . . .
N2 N 1.4038(6) 0.3368(4) 0.8427(3) 0.0409(11) Uani 1 1 d . . .
N3 N 1.2240(6) 0.6591(4) 0.6544(3) 0.0341(10) Uani 1 1 d . . .
N4 N 0.9881(7) -0.1485(4) 0.9861(3) 0.0411(12) Uani 1 1 d . . .
C1 C 0.4218(6) 0.8928(4) 0.8332(3) 0.0230(9) Uani 1 1 d . . .
C2 C 0.4203(7) 0.8319(4) 0.7556(3) 0.0284(10) Uani 1 1 d . . .
H2A H 0.4405 0.7473 0.7600 0.034 Uiso 1 1 calc R . .
C3 C 0.3891(7) 0.8965(4) 0.6718(3) 0.0283(10) Uani 1 1 d . . .
H3A H 0.3885 0.8560 0.6182 0.034 Uiso 1 1 calc R . .
C4 C 0.3585(6) 1.0205(4) 0.6656(3) 0.0242(9) Uani 1 1 d . . .
C5 C 0.3609(7) 1.0798(4) 0.7440(3) 0.0301(10) Uani 1 1 d . . .
H5A H 0.3404 1.1644 0.7401 0.036 Uiso 1 1 calc R . .
C6 C 0.3930(7) 1.0157(5) 0.8274(3) 0.0323(11) Uani 1 1 d . . .
H6A H 0.3954 1.0560 0.8808 0.039 Uiso 1 1 calc R . .
C7 C 0.3212(6) 1.0868(4) 0.5785(3) 0.0251(10) Uani 1 1 d . . .
C8 C 0.7124(6) 0.5762(4) 0.8990(3) 0.0236(9) Uani 1 1 d . . .
C9 C 0.7585(7) 0.4578(4) 0.8738(3) 0.0273(10) Uani 1 1 d . . .
H9A H 0.6680 0.4196 0.8680 0.033 Uiso 1 1 calc R . .
C10 C 0.9380(6) 0.3961(4) 0.8574(3) 0.0254(10) Uani 1 1 d . . .
H10A H 0.9713 0.3151 0.8409 0.030 Uiso 1 1 calc R . .
C11 C 1.0688(6) 0.4539(4) 0.8653(3) 0.0238(9) Uani 1 1 d . . .
C12 C 1.0219(6) 0.5733(4) 0.8877(3) 0.0249(9) Uani 1 1 d . . .
H12A H 1.1118 0.6128 0.8909 0.030 Uiso 1 1 calc R . .
C13 C 0.8423(6) 0.6340(4) 0.9052(3) 0.0259(10) Uani 1 1 d . . .
H13A H 0.8088 0.7151 0.9214 0.031 Uiso 1 1 calc R . .
C14 C 1.2562(7) 0.3885(4) 0.8520(3) 0.0282(10) Uani 1 1 d . . .
C15 C 0.7594(6) 0.4155(4) 0.6016(3) 0.0225(9) Uani 1 1 d . . .
C16 C 0.9413(6) 0.3587(4) 0.5965(3) 0.0232(9) Uani 1 1 d . . .
H16A H 0.9846 0.2765 0.5835 0.028 Uiso 1 1 calc R . .
C17 C 1.0594(6) 0.4233(4) 0.6104(3) 0.0241(9) Uani 1 1 d . . .
H17A H 1.1844 0.3853 0.6064 0.029 Uiso 1 1 calc R . .
C18 C 0.9958(6) 0.5431(4) 0.6303(3) 0.0232(9) Uani 1 1 d . . .
C19 C 0.8119(7) 0.6004(4) 0.6354(3) 0.0270(10) Uani 1 1 d . . .
H19A H 0.7691 0.6827 0.6481 0.032 Uiso 1 1 calc R . .
C20 C 0.6925(6) 0.5365(4) 0.6218(3) 0.0262(10) Uani 1 1 d . . .
H20A H 0.5674 0.5741 0.6261 0.031 Uiso 1 1 calc R . .
C21 C 1.1214(7) 0.6088(4) 0.6437(3) 0.0271(10) Uani 1 1 d . . .
C22 C 0.7980(6) 0.0971(4) 0.6686(3) 0.0210(9) Uani 1 1 d . . .
C23 C 0.8762(7) -0.0253(4) 0.6693(3) 0.0311(11) Uani 1 1 d . . .
H23A H 0.8935 -0.0661 0.6140 0.037 Uiso 1 1 calc R . .
C24 C 0.9290(7) -0.0878(4) 0.7512(4) 0.0314(11) Uani 1 1 d . . .
H24A H 0.9840 -0.1719 0.7522 0.038 Uiso 1 1 calc R . .
C25 C 0.9014(6) -0.0275(4) 0.8323(3) 0.0246(9) Uani 1 1 d . . .
C26 C 0.8232(6) 0.0955(4) 0.8304(3) 0.0234(9) Uani 1 1 d . . .
H26A H 0.8048 0.1366 0.8857 0.028 Uiso 1 1 calc R . .
C27 C 0.7719(6) 0.1583(4) 0.7486(3) 0.0240(9) Uani 1 1 d . . .
H27A H 0.7193 0.2426 0.7471 0.029 Uiso 1 1 calc R . .
C28 C 0.9514(7) -0.0936(4) 0.9179(4) 0.0283(10) Uani 1 1 d . . .


_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 C1 1.792(5) . ?
S1 S2 2.0299(18) . ?
S2 C8 1.782(5) . ?
S3 C15 1.785(5) . ?
S3 S4 2.0282(17) . ?
S4 C22 1.792(4) . ?
N1 C7 1.149(6) . ?
N2 C14 1.141(7) . ?
N3 C21 1.150(7) . ?
N4 C28 1.152(7) . ?
C1 C6 1.380(7) . ?
C1 C2 1.391(6) . ?
C2 C3 1.384(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(7) . ?
C4 C7 1.440(7) . ?
C5 C6 1.377(7) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C8 C13 1.382(6) . ?
C8 C9 1.395(7) . ?
C9 C10 1.389(7) . ?
C9 H9A 0.9500 . ?
C10 C11 1.394(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.392(6) . ?
C11 C14 1.448(7) . ?
C12 C13 1.389(7) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C15 C16 1.386(6) . ?
C15 C20 1.402(7) . ?
C16 C17 1.387(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.387(6) . ?
C17 H17A 0.9500 . ?
C18 C19 1.401(7) . ?
C18 C21 1.443(7) . ?
C19 C20 1.388(7) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C22 C23 1.383(7) . ?
C22 C27 1.388(6) . ?
C23 C24 1.382(7) . ?
C23 H23A 0.9500 . ?
C24 C25 1.395(7) . ?
C24 H24A 0.9500 . ?
C25 C26 1.388(6) . ?
C25 C28 1.437(7) . ?
C26 C27 1.379(7) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?

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
C1 S1 S2 105.23(16) . . ?
C8 S2 S1 105.31(16) . . ?
C15 S3 S4 104.92(16) . . ?
C22 S4 S3 105.24(15) . . ?
C6 C1 C2 120.9(4) . . ?
C6 C1 S1 116.4(3) . . ?
C2 C1 S1 122.7(4) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 C7 119.8(4) . . ?
C5 C4 C7 120.5(4) . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
N1 C7 C4 178.5(5) . . ?
C13 C8 C9 121.0(4) . . ?
C13 C8 S2 122.9(4) . . ?
C9 C8 S2 116.0(3) . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 C14 119.3(4) . . ?
C10 C11 C14 119.8(4) . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
C8 C13 C12 119.9(4) . . ?
C8 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
N2 C14 C11 179.2(5) . . ?
C16 C15 C20 121.3(4) . . ?
C16 C15 S3 122.8(4) . . ?
C20 C15 S3 115.9(3) . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 H16A 120.4 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 C21 119.3(4) . . ?
C19 C18 C21 120.3(4) . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?
C19 C20 C15 119.0(4) . . ?
C19 C20 H20A 120.5 . . ?
C15 C20 H20A 120.5 . . ?
N3 C21 C18 178.6(5) . . ?
C23 C22 C27 121.1(4) . . ?
C23 C22 S4 116.0(3) . . ?
C27 C22 S4 122.9(4) . . ?
C22 C23 C24 119.4(4) . . ?
C22 C23 H23A 120.3 . . ?
C24 C23 H23A 120.3 . . ?
C23 C24 C25 119.9(4) . . ?
C23 C24 H24A 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 C28 120.3(4) . . ?
C24 C25 C28 119.7(4) . . ?
C27 C26 C25 120.2(4) . . ?
C27 C26 H26A 119.9 . . ?
C25 C26 H26A 119.9 . . ?
C26 C27 C22 119.4(4) . . ?
C26 C27 H27A 120.3 . . ?
C22 C27 H27A 120.3 . . ?
N4 C28 C25 178.0(5) . . ?

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
C1 S1 S2 C8 90.1(2) . . . . ?
C15 S3 S4 C22 78.9(2) . . . . ?
S2 S1 C1 C6 176.7(3) . . . . ?
S2 S1 C1 C2 -3.0(4) . . . . ?
C6 C1 C2 C3 -0.2(7) . . . . ?
S1 C1 C2 C3 179.5(4) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C2 C3 C4 C7 -178.2(4) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C7 C4 C5 C6 178.6(4) . . . . ?
C4 C5 C6 C1 -0.4(8) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
S1 C1 C6 C5 -179.1(4) . . . . ?
S1 S2 C8 C13 10.5(4) . . . . ?
S1 S2 C8 C9 -173.1(3) . . . . ?
C13 C8 C9 C10 1.9(7) . . . . ?
S2 C8 C9 C10 -174.6(3) . . . . ?
C8 C9 C10 C11 -0.7(7) . . . . ?
C9 C10 C11 C12 -1.2(7) . . . . ?
C9 C10 C11 C14 177.4(4) . . . . ?
C10 C11 C12 C13 2.0(7) . . . . ?
C14 C11 C12 C13 -176.6(4) . . . . ?
C9 C8 C13 C12 -1.0(7) . . . . ?
S2 C8 C13 C12 175.2(3) . . . . ?
C11 C12 C13 C8 -0.9(7) . . . . ?
S4 S3 C15 C16 -1.4(4) . . . . ?
S4 S3 C15 C20 -180.0(3) . . . . ?
C20 C15 C16 C17 -0.8(7) . . . . ?
S3 C15 C16 C17 -179.3(3) . . . . ?
C15 C16 C17 C18 0.7(7) . . . . ?
C16 C17 C18 C19 -0.7(7) . . . . ?
C16 C17 C18 C21 -179.4(4) . . . . ?
C17 C18 C19 C20 0.9(7) . . . . ?
C21 C18 C19 C20 179.6(4) . . . . ?
C18 C19 C20 C15 -1.0(7) . . . . ?
C16 C15 C20 C19 1.0(7) . . . . ?
S3 C15 C20 C19 179.6(3) . . . . ?
S3 S4 C22 C23 171.6(3) . . . . ?
S3 S4 C22 C27 -10.0(4) . . . . ?
C27 C22 C23 C24 0.2(7) . . . . ?
S4 C22 C23 C24 178.6(4) . . . . ?
C22 C23 C24 C25 0.6(8) . . . . ?
C23 C24 C25 C26 -0.8(7) . . . . ?
C23 C24 C25 C28 178.0(5) . . . . ?
C24 C25 C26 C27 0.2(7) . . . . ?
C28 C25 C26 C27 -178.6(4) . . . . ?
C25 C26 C27 C22 0.6(7) . . . . ?
C23 C22 C27 C26 -0.8(7) . . . . ?
S4 C22 C27 C26 -179.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        69.99
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         1.016
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.148
