data_exp_1
_audit_creation_date              2017-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number      '2014/7'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
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          'C12 H13 N O2 S'
_chemical_formula_sum             'C12 H13 N O2 S'
_chemical_formula_weight          235.29
_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'
 'N' 'N' 0.0061 0.0033 '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       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                    10.7579(6)
_cell_length_b                    9.2297(5)
_cell_length_c                    11.7358(7)
_cell_angle_alpha                 90
_cell_angle_beta                  92.003(5)
_cell_angle_gamma                 90
_cell_volume                      1164.56(11)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     4075
_cell_measurement_temperature     293.00(10)
_cell_measurement_theta_max       30.1330
_cell_measurement_theta_min       3.5080
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.262
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.37254
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        'platelet'
_exptl_crystal_F_000              496
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.08
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0542
_diffrn_reflns_av_unetI/netI      0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_number             12688
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          30.607
_diffrn_reflns_theta_min          3.422
_diffrn_ambient_environment       air
_diffrn_ambient_temperature       293.00(10)
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -15.00  11.00   0.50   12.00    --   -0.30  38.00 -90.00   52
  2  ω    -17.00   9.00   0.50   12.00    --   -0.30  38.00-150.00   52
  3  ω    -24.00  89.00   0.50   12.00    --   -0.30  38.00-180.00  226
  4  ω    -24.00  44.00   0.50   12.00    --   -0.30  38.00 120.00  136
  5  ω    -20.00   7.00   0.50   12.00    --   -0.30  29.00  10.00   54
;
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'Rigaku XtaLAB Pro: Kappa single'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11       -0.0181174000
_diffrn_orient_matrix_UB_12       -0.0103827000
_diffrn_orient_matrix_UB_13       0.0569420000
_diffrn_orient_matrix_UB_21       0.0581579000
_diffrn_orient_matrix_UB_22       0.0277091000
_diffrn_orient_matrix_UB_23       0.0202985000
_diffrn_orient_matrix_UB_31       -0.0253995000
_diffrn_orient_matrix_UB_32       0.0709235000
_diffrn_orient_matrix_UB_33       0.0004433000
_diffrn_radiation_monochromator   'multi-layer optics'
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'microfocus sealed X-ray tube'
_diffrn_source_type               'Rigaku mm003(Mo) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 2557
_reflns_number_total              3211
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      26.32
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction         'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.236
_refine_diff_density_min          -0.277
_refine_diff_density_rms          0.052
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      145
_refine_ls_number_reflns          3211
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0555
_refine_ls_R_factor_gt            0.0430
_refine_ls_restrained_S_all       1.052
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0595P)²+0.1824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1159
_refine_ls_wR_factor_ref          0.1256
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C9(H9), C11(H11), C10(H10)
;
_atom_sites_solution_hydrogens    geom
_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 0.35309(4) 0.38750(4) 0.57138(3) 0.04625(14) Uani 1 1 d . . . . .
 O1 O 0.07551(11) 0.02089(12) 0.34121(10) 0.0553(3) Uani 1 1 d . . . . .
 O2 O 0.14252(11) 0.61440(12) 0.44452(11) 0.0569(3) Uani 1 1 d . . . . .
 N1 N 0.15878(10) 0.27816(12) 0.44907(9) 0.0377(3) Uani 1 1 d . . . . .
 C7 C 0.29622(12) 0.55680(13) 0.31109(11) 0.0363(3) Uani 1 1 d . . . . .
 C8 C 0.38279(13) 0.45684(15) 0.27433(12) 0.0410(3) Uani 1 1 d . . . . .
 H8 H 0.3929 0.3691 0.3125 0.049 Uiso 1 1 calc R . . . .
 C1 C 0.23705(12) 0.38559(13) 0.47417(11) 0.0338(3) Uani 1 1 d . . . . .
 C6 C 0.21831(12) 0.52782(13) 0.41013(12) 0.0373(3) Uani 1 1 d . . . . .
 C5 C 0.06300(12) 0.28275(16) 0.35662(13) 0.0432(3) Uani 1 1 d . . . . .
 H5A H 0.0705 0.3719 0.3136 0.052 Uiso 1 1 calc R . . . .
 H5B H -0.0190 0.2802 0.3883 0.052 Uiso 1 1 calc R . . . .
 C2 C 0.16267(15) 0.13945(16) 0.51029(13) 0.0468(3) Uani 1 1 d . . . . .
 H2A H 0.0876 0.1279 0.5529 0.056 Uiso 1 1 calc R . . . .
 H2B H 0.2334 0.1379 0.5639 0.056 Uiso 1 1 calc R . . . .
 C12 C 0.28109(16) 0.68802(15) 0.25157(15) 0.0510(4) Uani 1 1 d . . . . .
 H12 H 0.2231 0.7558 0.2746 0.061 Uiso 1 1 calc R . . . .
 C4 C 0.07954(15) 0.15437(18) 0.27931(13) 0.0489(3) Uani 1 1 d . . . . .
 H4A H 0.0143 0.1546 0.2202 0.059 Uiso 1 1 calc R . . . .
 H4B H 0.1588 0.1622 0.2428 0.059 Uiso 1 1 calc R . . . .
 C9 C 0.45423(15) 0.48700(19) 0.18110(14) 0.0525(4) Uani 1 1 d . . . . .
 H9 H 0.5122 0.4197 0.1572 0.063 Uiso 1 1 calc R . . . .
 C11 C 0.35296(19) 0.71592(19) 0.15852(16) 0.0640(5) Uani 1 1 d . . . . .
 H11 H 0.3429 0.8027 0.1189 0.077 Uiso 1 1 calc R . . . .
 C3 C 0.17325(17) 0.01726(17) 0.42620(15) 0.0542(4) Uani 1 1 d . . . . .
 H3A H 0.2526 0.0238 0.3898 0.065 Uiso 1 1 calc R . . . .
 H3B H 0.1708 -0.0744 0.4665 0.065 Uiso 1 1 calc R . . . .
 C10 C 0.43945(18) 0.6160(2) 0.12397(15) 0.0605(5) Uani 1 1 d . . . . .
 H10 H 0.4879 0.6362 0.0618 0.073 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 1.6616(13) . ?
 O1 C4 1.432(2) . ?
 O1 C3 1.424(2) . ?
 O2 C6 1.2204(16) . ?
 N1 C1 1.3272(16) . ?
 N1 C5 1.4705(17) . ?
 N1 C2 1.4679(17) . ?
 C7 C8 1.3903(19) . ?
 C7 C6 1.4809(19) . ?
 C7 C12 1.4047(18) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.387(2) . ?
 C1 C6 1.5225(17) . ?
 C5 H5A 0.9700 . ?
 C5 H5B 0.9700 . ?
 C5 C4 1.507(2) . ?
 C2 H2A 0.9700 . ?
 C2 H2B 0.9700 . ?
 C2 C3 1.506(2) . ?
 C12 H12 0.9300 . ?
 C12 C11 1.384(3) . ?
 C4 H4A 0.9700 . ?
 C4 H4B 0.9700 . ?
 C9 H9 0.9300 . ?
 C9 C10 1.373(2) . ?
 C11 H11 0.9300 . ?
 C11 C10 1.381(3) . ?
 C3 H3A 0.9700 . ?
 C3 H3B 0.9700 . ?
 C10 H10 0.9300 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C3 O1 C4 109.93(11) . . ?
 C1 N1 C5 124.40(11) . . ?
 C1 N1 C2 122.41(11) . . ?
 C2 N1 C5 113.17(11) . . ?
 C8 C7 C6 121.83(11) . . ?
 C8 C7 C12 119.01(13) . . ?
 C12 C7 C6 119.15(13) . . ?
 C7 C8 H8 119.8 . . ?
 C9 C8 C7 120.48(13) . . ?
 C9 C8 H8 119.8 . . ?
 N1 C1 S1 128.02(10) . . ?
 N1 C1 C6 117.56(11) . . ?
 C6 C1 S1 114.40(9) . . ?
 O2 C6 C7 122.97(12) . . ?
 O2 C6 C1 118.68(12) . . ?
 C7 C6 C1 118.32(11) . . ?
 N1 C5 H5A 109.9 . . ?
 N1 C5 H5B 109.9 . . ?
 N1 C5 C4 109.10(11) . . ?
 H5A C5 H5B 108.3 . . ?
 C4 C5 H5A 109.9 . . ?
 C4 C5 H5B 109.9 . . ?
 N1 C2 H2A 109.8 . . ?
 N1 C2 H2B 109.8 . . ?
 N1 C2 C3 109.51(12) . . ?
 H2A C2 H2B 108.2 . . ?
 C3 C2 H2A 109.8 . . ?
 C3 C2 H2B 109.8 . . ?
 C7 C12 H12 120.2 . . ?
 C11 C12 C7 119.64(15) . . ?
 C11 C12 H12 120.2 . . ?
 O1 C4 C5 111.40(13) . . ?
 O1 C4 H4A 109.3 . . ?
 O1 C4 H4B 109.3 . . ?
 C5 C4 H4A 109.3 . . ?
 C5 C4 H4B 109.3 . . ?
 H4A C4 H4B 108.0 . . ?
 C8 C9 H9 120.0 . . ?
 C10 C9 C8 120.09(16) . . ?
 C10 C9 H9 120.0 . . ?
 C12 C11 H11 119.7 . . ?
 C10 C11 C12 120.55(14) . . ?
 C10 C11 H11 119.7 . . ?
 O1 C3 C2 111.75(13) . . ?
 O1 C3 H3A 109.3 . . ?
 O1 C3 H3B 109.3 . . ?
 C2 C3 H3A 109.3 . . ?
 C2 C3 H3B 109.3 . . ?
 H3A C3 H3B 107.9 . . ?
 C9 C10 C11 120.22(16) . . ?
 C9 C10 H10 119.9 . . ?
 C11 C10 H10 119.9 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.160
_oxdiff_exptl_absorpt_empirical_full_min 0.565
