data_stein1e
_audit_creation_date              2017-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

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. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common             ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety          'C17 H12 Cl N O3 S'
_chemical_formula_sum             'C17 H12 Cl N O3 S'
_chemical_formula_weight          345.79
_chemical_melting_point           ?
_chemical_oxdiff_formula          'C17 H12 Cl N O3 S'
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'
 'Cl' 'Cl' 0.1484 0.1585 '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'

_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_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x+1/2, -y, z+1/2'
 3 'x+1/2, -y+1/2, -z'
 4 '-x, y+1/2, -z+1/2'
 5 '-x, -y, -z'
 6 'x-1/2, y, -z-1/2'
 7 '-x-1/2, y-1/2, z'
 8 'x, -y-1/2, z-1/2'

_cell_length_a                    11.8228(2)
_cell_length_b                    12.38285(19)
_cell_length_c                    20.3843(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2984.27(9)
_cell_formula_units_Z             8
_cell_measurement_reflns_used     12569
_cell_measurement_temperature     100(2)
_cell_measurement_theta_max       29.4490
_cell_measurement_theta_min       3.8050
_exptl_absorpt_coefficient_mu     0.410
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.91732
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.539
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        prism
_exptl_crystal_F_000              1424
_exptl_crystal_size_max           0.48
_exptl_crystal_size_mid           0.44
_exptl_crystal_size_min           0.38
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0231
_diffrn_reflns_av_unetI/netI      0.0184
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_number             21307
_diffrn_reflns_theta_full         27.00
_diffrn_reflns_theta_max          29.64
_diffrn_reflns_theta_min          3.44
_diffrn_ambient_temperature       100.15
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  10.3756
_diffrn_detector_type             Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -87.00  22.00   1.00    6.79    --  -10.69 -77.00  30.00  109
  2  ω    -30.00  91.00   1.00    6.79    --   10.77  19.00   0.00  121
  3  ω     -1.00  36.00   1.00    6.79    --   10.77-122.00 -69.00   37
;
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11       -0.0068979000
_diffrn_orient_matrix_UB_12       -0.0271710000
_diffrn_orient_matrix_UB_13       -0.0303839000
_diffrn_orient_matrix_UB_21       0.0000359000
_diffrn_orient_matrix_UB_22       -0.0503205000
_diffrn_orient_matrix_UB_23       0.0166082000
_diffrn_orient_matrix_UB_31       -0.0595915000
_diffrn_orient_matrix_UB_32       0.0031081000
_diffrn_orient_matrix_UB_33       0.0035124000
_diffrn_radiation_monochromator   mirror
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'micro-focus sealed X-ray tube'
_diffrn_source_type               'SuperNova (Mo) X-ray Source'
_reflns_number_gt                 3493
_reflns_number_total              3906
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      26.32
_reflns_threshold_expression      >2sigma(I)
_computing_cell_refinement        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction         'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'XL (Sheldrick, 2008)'
_computing_structure_solution     'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max          0.342
_refine_diff_density_min          -0.338
_refine_diff_density_rms          0.061
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.039
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      213
_refine_ls_number_reflns          3906
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0347
_refine_ls_R_factor_gt            0.0302
_refine_ls_restrained_S_all       1.039
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0386P)²+1.4345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0754
_refine_ls_wR_factor_ref          0.0784
_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. 
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    difmap
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_calc_flag
  _atom_site_disorder_assembly
  _atom_site_disorder_group
  _atom_site_refinement_flags_posn
 Cl1 Cl 0.36577(3) 0.33460(2) 0.128978(16) 0.02230(9) Uani 1 d . . .
 S1 S 0.67733(2) 0.49876(2) 0.101631(15) 0.01559(8) Uani 1 d . . .
 O1 O 0.38559(8) 0.90442(7) 0.01677(5) 0.02123(19) Uani 1 d . . .
 H1 H 0.4032(18) 0.9712(18) 0.0086(10) 0.047(6) Uiso 1 d . . .
 O2 O 0.57213(8) 0.88865(7) -0.00093(5) 0.0224(2) Uani 1 d . . .
 O3 O 0.68254(8) 0.22935(7) 0.11251(4) 0.0221(2) Uani 1 d . . .
 N1 N 0.62842(9) 0.27535(8) 0.21572(5) 0.0163(2) Uani 1 d . . .
 C1 C 0.58664(10) 0.39573(9) 0.12502(6) 0.0142(2) Uani 1 d . . .
 C2 C 0.47676(10) 0.42083(9) 0.11358(6) 0.0149(2) Uani 1 d . . .
 C3 C 0.45991(10) 0.52673(9) 0.08649(6) 0.0145(2) Uani 1 d . . .
 C4 C 0.35958(10) 0.58040(10) 0.06966(6) 0.0172(2) Uani 1 d . . .
 H4 H 0.2885 0.5455 0.0745 0.021 Uiso 1 calc . . R
 C5 C 0.36578(10) 0.68486(10) 0.04597(6) 0.0181(2) Uani 1 d . . .
 H5 H 0.2983 0.7228 0.0355 0.022 Uiso 1 calc . . R
 C6 C 0.47132(10) 0.73541(9) 0.03717(6) 0.0158(2) Uani 1 d . . .
 C7 C 0.57140(10) 0.68266(9) 0.05207(6) 0.0154(2) Uani 1 d . . .
 H7 H 0.6425 0.7165 0.0452 0.019 Uiso 1 calc . . R
 C8 C 0.56452(10) 0.57868(9) 0.07741(6) 0.0140(2) Uani 1 d . . .
 C9 C 0.48032(11) 0.84936(9) 0.01526(6) 0.0171(2) Uani 1 d . . .
 C10 C 0.63601(9) 0.29201(9) 0.15026(6) 0.0148(2) Uani 1 d . . .
 C11 C 0.67760(11) 0.17778(10) 0.24457(7) 0.0206(3) Uani 1 d . . .
 H11A H 0.7184 0.1374 0.2107 0.031 Uiso 1 calc . . GR
 H11B H 0.6172 0.1326 0.2627 0.031 Uiso 1 calc . . GR
 H11C H 0.7302 0.1981 0.2796 0.031 Uiso 1 calc . . GR
 C12 C 0.57637(10) 0.35058(9) 0.26003(6) 0.0155(2) Uani 1 d . . .
 C13 C 0.47594(11) 0.32161(10) 0.29075(6) 0.0189(2) Uani 1 d . . .
 H13 H 0.4416 0.2540 0.2815 0.023 Uiso 1 calc . . R
 C14 C 0.42637(11) 0.39225(11) 0.33493(6) 0.0210(3) Uani 1 d . . .
 H14 H 0.3582 0.3724 0.3564 0.025 Uiso 1 calc . . R
 C15 C 0.47551(11) 0.49165(10) 0.34805(6) 0.0210(3) Uani 1 d . . .
 H15 H 0.4400 0.5406 0.3774 0.025 Uiso 1 calc . . R
 C16 C 0.57698(11) 0.51930(10) 0.31798(7) 0.0222(3) Uani 1 d . . .
 H16 H 0.6114 0.5869 0.3273 0.027 Uiso 1 calc . . R
 C17 C 0.62822(11) 0.44830(10) 0.27440(6) 0.0195(2) Uani 1 d . . .
 H17 H 0.6984 0.4665 0.2545 0.023 Uiso 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
 Cl1 C2 1.7207(12) . ?
 S1 C1 1.7334(12) . ?
 S1 C8 1.7326(11) . ?
 O1 H1 0.87(2) . ?
 O1 C9 1.3116(15) . ?
 O2 C9 1.2345(16) . ?
 O3 C10 1.2234(15) . ?
 N1 C10 1.3532(16) . ?
 N1 C11 1.4641(15) . ?
 N1 C12 1.4360(15) . ?
 C1 C2 1.3560(16) . ?
 C1 C10 1.5017(15) . ?
 C2 C3 1.4368(15) . ?
 C3 C4 1.4022(16) . ?
 C3 C8 1.4064(16) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.3827(17) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.4075(17) . ?
 C6 C7 1.3852(16) . ?
 C6 C9 1.4839(16) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.3896(15) . ?
 C11 H11A 0.9800 . ?
 C11 H11B 0.9800 . ?
 C11 H11C 0.9800 . ?
 C12 C13 1.3894(17) . ?
 C12 C17 1.3878(17) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.3856(18) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.3871(18) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.3900(19) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.3890(18) . ?
 C17 H17 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 91.30(6) . . ?
 C9 O1 H1 106.6(14) . . ?
 C10 N1 C11 119.70(10) . . ?
 C10 N1 C12 123.35(10) . . ?
 C12 N1 C11 116.92(10) . . ?
 C2 C1 S1 112.12(9) . . ?
 C2 C1 C10 128.86(11) . . ?
 C10 C1 S1 118.90(8) . . ?
 C1 C2 Cl1 123.85(9) . . ?
 C1 C2 C3 114.09(10) . . ?
 C3 C2 Cl1 122.06(9) . . ?
 C4 C3 C2 130.08(11) . . ?
 C4 C3 C8 119.67(10) . . ?
 C8 C3 C2 110.25(10) . . ?
 C3 C4 H4 120.5 . . ?
 C5 C4 C3 118.94(11) . . ?
 C5 C4 H4 120.5 . . ?
 C4 C5 H5 119.7 . . ?
 C4 C5 C6 120.50(11) . . ?
 C6 C5 H5 119.7 . . ?
 C5 C6 C9 121.65(11) . . ?
 C7 C6 C5 121.31(11) . . ?
 C7 C6 C9 116.95(11) . . ?
 C6 C7 H7 121.0 . . ?
 C6 C7 C8 117.93(11) . . ?
 C8 C7 H7 121.0 . . ?
 C3 C8 S1 112.22(8) . . ?
 C7 C8 S1 126.16(9) . . ?
 C7 C8 C3 121.61(10) . . ?
 O1 C9 C6 115.22(11) . . ?
 O2 C9 O1 123.52(11) . . ?
 O2 C9 C6 121.22(11) . . ?
 O3 C10 N1 123.60(11) . . ?
 O3 C10 C1 120.11(11) . . ?
 N1 C10 C1 116.26(10) . . ?
 N1 C11 H11A 109.5 . . ?
 N1 C11 H11B 109.5 . . ?
 N1 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 C13 C12 N1 118.83(10) . . ?
 C17 C12 N1 120.60(11) . . ?
 C17 C12 C13 120.50(11) . . ?
 C12 C13 H13 120.3 . . ?
 C14 C13 C12 119.44(11) . . ?
 C14 C13 H13 120.3 . . ?
 C13 C14 H14 119.7 . . ?
 C13 C14 C15 120.55(12) . . ?
 C15 C14 H14 119.7 . . ?
 C14 C15 H15 120.2 . . ?
 C14 C15 C16 119.67(12) . . ?
 C16 C15 H15 120.2 . . ?
 C15 C16 H16 119.9 . . ?
 C17 C16 C15 120.17(12) . . ?
 C17 C16 H16 119.9 . . ?
 C12 C17 C16 119.62(12) . . ?
 C12 C17 H17 120.2 . . ?
 C16 C17 H17 120.2 . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
 O1 H1 O2 0.87(2) 1.77(2) 2.6305(13) 172(2) 5_675

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
 Cl1 C2 C3 C4 1.82(18) . . . . ?
 Cl1 C2 C3 C8 -178.51(9) . . . . ?
 S1 C1 C2 Cl1 178.02(7) . . . . ?
 S1 C1 C2 C3 -1.41(14) . . . . ?
 S1 C1 C10 O3 -72.57(14) . . . . ?
 S1 C1 C10 N1 105.56(11) . . . . ?
 N1 C12 C13 C14 178.31(11) . . . . ?
 N1 C12 C17 C16 -179.26(11) . . . . ?
 C1 S1 C8 C3 -0.62(9) . . . . ?
 C1 S1 C8 C7 178.96(11) . . . . ?
 C1 C2 C3 C4 -178.74(12) . . . . ?
 C1 C2 C3 C8 0.93(15) . . . . ?
 C2 C1 C10 O3 103.15(15) . . . . ?
 C2 C1 C10 N1 -78.72(16) . . . . ?
 C2 C3 C4 C5 177.99(12) . . . . ?
 C2 C3 C8 S1 -0.03(13) . . . . ?
 C2 C3 C8 C7 -179.64(10) . . . . ?
 C3 C4 C5 C6 1.74(18) . . . . ?
 C4 C3 C8 S1 179.68(9) . . . . ?
 C4 C3 C8 C7 0.07(18) . . . . ?
 C4 C5 C6 C7 -0.23(19) . . . . ?
 C4 C5 C6 C9 -176.64(11) . . . . ?
 C5 C6 C7 C8 -1.35(18) . . . . ?
 C5 C6 C9 O1 12.28(17) . . . . ?
 C5 C6 C9 O2 -169.98(12) . . . . ?
 C6 C7 C8 S1 -178.13(9) . . . . ?
 C6 C7 C8 C3 1.42(18) . . . . ?
 C7 C6 C9 O1 -164.28(11) . . . . ?
 C7 C6 C9 O2 13.45(17) . . . . ?
 C8 S1 C1 C2 1.16(10) . . . . ?
 C8 S1 C1 C10 177.56(10) . . . . ?
 C8 C3 C4 C5 -1.66(18) . . . . ?
 C9 C6 C7 C8 175.23(10) . . . . ?
 C10 N1 C12 C13 112.09(13) . . . . ?
 C10 N1 C12 C17 -71.01(16) . . . . ?
 C10 C1 C2 Cl1 2.07(19) . . . . ?
 C10 C1 C2 C3 -177.37(11) . . . . ?
 C11 N1 C10 O3 -0.05(18) . . . . ?
 C11 N1 C10 C1 -178.10(10) . . . . ?
 C11 N1 C12 C13 -69.55(14) . . . . ?
 C11 N1 C12 C17 107.35(13) . . . . ?
 C12 N1 C10 O3 178.26(11) . . . . ?
 C12 N1 C10 C1 0.21(16) . . . . ?
 C12 C13 C14 C15 0.72(19) . . . . ?
 C13 C12 C17 C16 -2.42(19) . . . . ?
 C13 C14 C15 C16 -1.81(19) . . . . ?
 C14 C15 C16 C17 0.8(2) . . . . ?
 C15 C16 C17 C12 1.3(2) . . . . ?
 C17 C12 C13 C14 1.41(18) . . . . ?


_olex2_date_sample_submission     2017-11-13
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.160
_oxdiff_exptl_absorpt_empirical_full_min 0.836
