data_gf02-060m
_audit_creation_date               2017-10-17
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.10.03 svn.r3461 for OlexSys, GUI svn.r5395)
;
_shelx_SHELXL_version_number       2017/1
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bruker (2013). SAINT-Plus V8.34A Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2016). APEX2 Version 2016.5-1. Bruker AXS Inc., Madison, Wisconsin, USA. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Krause, L., Herbst-Irmer, R., Sheldrick, G. M., and Stalke, D., J. Appl. Cryst. (2015). 48, 1907-1913. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790; Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984; Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575-580 Petricek,V., Dusek,M. & Palatinus,L.(2006). Jana2006. The crystallographic computing system. Institute of Physics, Praha, Czech Republic. Sheldrick, G.M. (2015). Acta Cryst. (2015). A71, 3-8. Sheldrick, G.M. (2015). Acta Cryst. (2015). C71, 3-8. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. Spek, A. L. (2015). Acta Cryst. C71, 9-18.
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.
Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C14 H10 O S'
_chemical_formula_sum              'C14 H10 O S'
_chemical_formula_weight           226.28
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             61
_space_group_name_H-M_alt          'P b c a'
_space_group_name_Hall             '-P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'

_cell_length_a                     10.5812(19)
_cell_length_b                     13.097(2)
_cell_length_c                     15.615(2)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2163.9(6)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      9412
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        39.964
_cell_measurement_theta_min        2.797
_shelx_estimated_absorpt_T_max     0.953
_shelx_estimated_absorpt_T_min     0.905
_exptl_absorpt_coefficient_mu      0.271
_exptl_absorpt_correction_T_max    0.7479
_exptl_absorpt_correction_T_min    0.6042
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS v.2016/2. (Krause, L. et al, 2015)'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              yellow
_exptl_crystal_colour_primary      yellow
_exptl_crystal_density_diffrn      1.389
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               944
_exptl_crystal_size_max            0.376
_exptl_crystal_size_mid            0.347
_exptl_crystal_size_min            0.18
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0583
_diffrn_reflns_av_unetI/netI       0.0401
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         18
_diffrn_reflns_limit_h_min         -19
_diffrn_reflns_limit_k_max         23
_diffrn_reflns_limit_k_min         -22
_diffrn_reflns_limit_l_max         28
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              39299
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           40.294
_diffrn_reflns_theta_min           2.609
_diffrn_ambient_temperature        100(2)
_diffrn_detector_area_resol_mean   7.495
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'Bruker D8 VENTURE diffractometer'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    'multilayer mirror'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'microfocus sealed tube'
_diffrn_source_current             1.4
_diffrn_source_voltage             50
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  5336
_reflns_number_total               6812
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection         'APEX2  v2016.5-1 (Bruker, 2014)'
_computing_data_reduction          'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max           0.596
_refine_diff_density_min           -0.490
_refine_diff_density_rms           0.075
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_hydrogen_treatment      refall
_refine_ls_matrix_type             full
_refine_ls_number_parameters       185
_refine_ls_number_reflns           6812
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0603
_refine_ls_R_factor_gt             0.0439
_refine_ls_restrained_S_all        1.050
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0642P)²+0.4331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1170
_refine_ls_wR_factor_ref           0.1296
_refine_special_details            ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 S1 S 0.86543(2) 0.25758(2) 0.27319(2) 0.02295(6) Uani 1 1 d . . . . .
 O1 O 0.72855(6) 0.41189(5) 0.30943(4) 0.01962(11) Uani 1 1 d . . . . .
 C4 C 0.63981(7) 0.37836(6) 0.49274(5) 0.01376(11) Uani 1 1 d . . . . .
 C2 C 0.64848(7) 0.25172(6) 0.36937(5) 0.01448(11) Uani 1 1 d . . . . .
 C5 C 0.64407(7) 0.46860(6) 0.44430(5) 0.01555(12) Uani 1 1 d . . . . .
 C3 C 0.60445(7) 0.28100(6) 0.45129(4) 0.01335(11) Uani 1 1 d . . . . .
 C7 C 0.52360(7) 0.21401(6) 0.49535(5) 0.01684(12) Uani 1 1 d . . . . .
 C11 C 0.66455(8) 0.38325(6) 0.58094(5) 0.01740(13) Uani 1 1 d . . . . .
 C10 C 0.61026(8) 0.15762(7) 0.33495(5) 0.01886(13) Uani 1 1 d . . . . .
 C9 C 0.52799(8) 0.09422(7) 0.37838(6) 0.02152(15) Uani 1 1 d . . . . .
 C8 C 0.48431(8) 0.12247(6) 0.45926(6) 0.01991(14) Uani 1 1 d . . . . .
 C14 C 0.67191(8) 0.56149(6) 0.48358(5) 0.01986(14) Uani 1 1 d . . . . .
 C6 C 0.62027(8) 0.46216(6) 0.35017(5) 0.01811(13) Uani 1 1 d . . . . .
 C13 C 0.69598(8) 0.56561(7) 0.57109(6) 0.02272(15) Uani 1 1 d . . . . .
 C1 C 0.74254(7) 0.31151(6) 0.31928(4) 0.01629(12) Uani 1 1 d . . . . .
 C12 C 0.69292(8) 0.47637(7) 0.61932(5) 0.02126(15) Uani 1 1 d . . . . .
 H10 H 0.6441(15) 0.1349(12) 0.2816(10) 0.033(4) Uiso 1 1 d . . . . .
 H6A H 0.6208(12) 0.5277(10) 0.3223(8) 0.020(3) Uiso 1 1 d . . . . .
 H11 H 0.6651(13) 0.3168(11) 0.6151(8) 0.021(3) Uiso 1 1 d . . . . .
 H9 H 0.5060(14) 0.0281(12) 0.3548(9) 0.033(4) Uiso 1 1 d . . . . .
 H13 H 0.7173(15) 0.6294(11) 0.5978(9) 0.031(4) Uiso 1 1 d . . . . .
 H7 H 0.4929(13) 0.2339(10) 0.5486(9) 0.021(3) Uiso 1 1 d . . . . .
 H8 H 0.4260(14) 0.0822(11) 0.4893(9) 0.025(3) Uiso 1 1 d . . . . .
 H14 H 0.6739(14) 0.6223(11) 0.4488(9) 0.025(3) Uiso 1 1 d . . . . .
 H12 H 0.7093(15) 0.4797(12) 0.6799(9) 0.032(4) Uiso 1 1 d . . . . .
 H6B H 0.5441(12) 0.4260(9) 0.3354(8) 0.015(3) Uiso 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 1.6455(8) . ?
 O1 C6 1.4666(10) . ?
 O1 C1 1.3318(10) . ?
 C4 C5 1.4039(11) . ?
 C4 C3 1.4781(11) . ?
 C4 C11 1.4033(11) . ?
 C2 C3 1.4143(10) . ?
 C2 C10 1.4040(11) . ?
 C2 C1 1.4886(11) . ?
 C5 C14 1.3939(12) . ?
 C5 C6 1.4937(11) . ?
 C3 C7 1.4054(10) . ?
 C7 C8 1.3883(12) . ?
 C7 H7 0.929(14) . ?
 C11 C12 1.3917(12) . ?
 C11 H11 1.020(14) . ?
 C10 C9 1.3811(13) . ?
 C10 H10 0.955(15) . ?
 C9 C8 1.3948(13) . ?
 C9 H9 0.970(15) . ?
 C8 H8 0.938(14) . ?
 C14 C13 1.3911(13) . ?
 C14 H14 0.964(14) . ?
 C6 H6A 0.962(13) . ?
 C6 H6B 0.963(13) . ?
 C13 C12 1.3907(13) . ?
 C13 H13 0.960(15) . ?
 C12 H12 0.963(14) . ?

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 O1 C6 118.68(6) . . ?
 C5 C4 C3 119.89(7) . . ?
 C11 C4 C5 118.97(7) . . ?
 C11 C4 C3 121.09(7) . . ?
 C3 C2 C1 123.57(7) . . ?
 C10 C2 C3 119.30(7) . . ?
 C10 C2 C1 116.95(7) . . ?
 C4 C5 C6 118.51(7) . . ?
 C14 C5 C4 120.30(7) . . ?
 C14 C5 C6 121.19(7) . . ?
 C2 C3 C4 123.13(6) . . ?
 C7 C3 C4 118.57(6) . . ?
 C7 C3 C2 118.29(7) . . ?
 C3 C7 H7 118.4(8) . . ?
 C8 C7 C3 121.51(7) . . ?
 C8 C7 H7 120.1(8) . . ?
 C4 C11 H11 118.4(7) . . ?
 C12 C11 C4 120.19(7) . . ?
 C12 C11 H11 121.4(7) . . ?
 C2 C10 H10 120.0(10) . . ?
 C9 C10 C2 121.42(8) . . ?
 C9 C10 H10 118.5(10) . . ?
 C10 C9 C8 119.60(8) . . ?
 C10 C9 H9 120.1(8) . . ?
 C8 C9 H9 120.1(8) . . ?
 C7 C8 C9 119.83(8) . . ?
 C7 C8 H8 118.7(9) . . ?
 C9 C8 H8 121.5(9) . . ?
 C5 C14 H14 118.6(9) . . ?
 C13 C14 C5 120.31(8) . . ?
 C13 C14 H14 121.1(9) . . ?
 O1 C6 C5 108.69(6) . . ?
 O1 C6 H6A 101.5(8) . . ?
 O1 C6 H6B 109.2(7) . . ?
 C5 C6 H6A 113.2(8) . . ?
 C5 C6 H6B 113.9(7) . . ?
 H6A C6 H6B 109.6(11) . . ?
 C14 C13 H13 120.2(9) . . ?
 C12 C13 C14 119.67(8) . . ?
 C12 C13 H13 120.1(9) . . ?
 O1 C1 S1 117.46(6) . . ?
 O1 C1 C2 120.37(6) . . ?
 C2 C1 S1 122.16(6) . . ?
 C11 C12 H12 120.1(9) . . ?
 C13 C12 C11 120.55(8) . . ?
 C13 C12 H12 119.3(9) . . ?

_olex2_submission_original_sample_id  gf02-060
_olex2_submission_special_instructions  'No special instructions were received'
