data_250319zyd
_audit_creation_date               2025-03-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_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           'C17 H21 N O S'
_chemical_formula_sum              'C17 H21 N O S'
_chemical_formula_weight           287.41
_chemical_absolute_configuration   ?
_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' 0.0137 0.0067 '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' 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S' 'S' 0.2925 0.4295 '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             19
_space_group_name_H-M_alt          'P 21 21 21'
_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'

_cell_length_a                     5.92330(10)
_cell_length_b                     12.0750(2)
_cell_length_c                     21.9490(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1569.88(5)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9972
_cell_measurement_temperature      170.00
_cell_measurement_theta_max        54.830
_cell_measurement_theta_min        3.636
_shelx_estimated_absorpt_T_max     0.943
_shelx_estimated_absorpt_T_min     0.823
_exptl_absorpt_coefficient_mu      1.194
_exptl_absorpt_correction_T_max    0.7508
_exptl_absorpt_correction_T_min    0.6146
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1450 before and 0.0668 after correction.
The Ratio of minimum to maximum transmission is 0.8186.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.216
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               616
_exptl_crystal_size_max            0.17
_exptl_crystal_size_mid            0.17
_exptl_crystal_size_min            0.05
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0468
_diffrn_reflns_av_unetI/netI       0.0335
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -4
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         26
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              13738
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           54.860
_diffrn_reflns_theta_min           3.635
_diffrn_ambient_temperature        170.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.34139
_diffrn_source                     ?
_diffrn_source_current             2.86
_diffrn_source_power               0.1995708
_diffrn_source_voltage             69.78
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.701
_reflns_Friedel_fraction_full      0.996
_reflns_Friedel_fraction_max       0.996
_reflns_number_gt                  2872
_reflns_number_total               2981
_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 V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.320
_refine_diff_density_min           -0.276
_refine_diff_density_rms           0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.036(8)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       188
_refine_ls_number_reflns           2981
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0317
_refine_ls_R_factor_gt             0.0302
_refine_ls_restrained_S_all        1.048
_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)+(0.0459P)²+0.3408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0812
_refine_ls_wR_factor_ref           0.0825
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens     mixed
_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 0.49106(9) 0.36376(4) 0.44935(2) 0.02146(15) Uani 1 1 d . . . . .
 O1 O 0.3799(3) 0.25826(12) 0.43625(7) 0.0309(4) Uani 1 1 d . . . . .
 N1 N 0.7455(3) 0.37338(17) 0.45282(9) 0.0305(4) Uani 1 1 d . . . . .
 H1 H 0.797(5) 0.342(3) 0.4844(16) 0.050(9) Uiso 1 1 d . . . . .
 C1 C 0.4140(3) 0.45744(16) 0.39124(9) 0.0193(4) Uani 1 1 d . . . . .
 C2 C 0.2089(4) 0.44338(19) 0.36184(10) 0.0274(5) Uani 1 1 d . . . . .
 H2 H 0.104030 0.389530 0.375815 0.033 Uiso 1 1 calc R U . . .
 C3 C 0.1586(4) 0.5092(2) 0.31156(11) 0.0295(5) Uani 1 1 d . . . . .
 H3 H 0.018109 0.499415 0.291371 0.035 Uiso 1 1 calc R U . . .
 C4 C 0.3081(4) 0.5890(2) 0.29008(10) 0.0266(5) Uani 1 1 d . . . . .
 C5 C 0.5083(4) 0.60417(19) 0.32251(11) 0.0309(5) Uani 1 1 d . . . . .
 H5 H 0.609979 0.660668 0.310070 0.037 Uiso 1 1 calc R U . . .
 C6 C 0.5631(4) 0.53884(19) 0.37255(10) 0.0261(5) Uani 1 1 d . . . . .
 H6 H 0.701314 0.549967 0.393653 0.031 Uiso 1 1 calc R U . . .
 C7 C 0.2663(4) 0.6522(2) 0.23043(12) 0.0386(6) Uani 1 1 d . . . . .
 C8 C 0.3835(6) 0.5876(3) 0.17924(12) 0.0522(8) Uani 1 1 d . . . . .
 H8A H 0.545137 0.581515 0.188193 0.078 Uiso 1 1 calc R U . . .
 H8B H 0.362585 0.626617 0.140512 0.078 Uiso 1 1 calc R U . . .
 H8C H 0.317737 0.513282 0.176318 0.078 Uiso 1 1 calc R U . . .
 C9 C 0.0148(5) 0.6578(4) 0.21516(18) 0.0884(16) Uani 1 1 d . . . . .
 H9A H -0.048285 0.582779 0.214575 0.133 Uiso 1 1 calc R U . . .
 H9B H -0.005163 0.692146 0.175071 0.133 Uiso 1 1 calc R U . . .
 H9C H -0.063413 0.702089 0.246058 0.133 Uiso 1 1 calc R U . . .
 C10 C 0.3651(7) 0.7696(3) 0.23263(15) 0.0607(9) Uani 1 1 d . . . . .
 H10A H 0.298467 0.810275 0.266836 0.091 Uiso 1 1 calc R U . . .
 H10B H 0.330778 0.808208 0.194456 0.091 Uiso 1 1 calc R U . . .
 H10C H 0.529105 0.765362 0.237998 0.091 Uiso 1 1 calc R U . . .
 C11 C 0.3523(4) 0.40952(19) 0.51819(10) 0.0269(5) Uani 1 1 d . . . . .
 H11A H 0.187435 0.410413 0.510843 0.032 Uiso 1 1 calc R U . . .
 H11B H 0.382062 0.354501 0.550655 0.032 Uiso 1 1 calc R U . . .
 C12 C 0.4219(4) 0.52153(18) 0.54101(9) 0.0254(5) Uani 1 1 d . . . . .
 C13 C 0.2813(5) 0.6114(2) 0.53217(12) 0.0360(6) Uani 1 1 d . . . . .
 H13 H 0.144342 0.602275 0.510208 0.043 Uiso 1 1 calc R U . . .
 C14 C 0.3379(6) 0.7148(2) 0.55502(15) 0.0515(8) Uani 1 1 d . . . . .
 H14 H 0.240016 0.776027 0.548641 0.062 Uiso 1 1 calc R U . . .
 C15 C 0.5359(6) 0.7288(2) 0.58692(13) 0.0524(8) Uani 1 1 d . . . . .
 H15 H 0.573841 0.799408 0.602975 0.063 Uiso 1 1 calc R U . . .
 C16 C 0.6792(5) 0.6400(3) 0.59557(13) 0.0484(7) Uani 1 1 d . . . . .
 H16 H 0.816694 0.649677 0.617223 0.058 Uiso 1 1 calc R U . . .
 C17 C 0.6223(5) 0.5364(2) 0.57257(11) 0.0360(6) Uani 1 1 d . . . . .
 H17 H 0.721330 0.475450 0.578521 0.043 Uiso 1 1 calc R U . . .


_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 O1 1.4625(16) . ?
 S1 N1 1.513(2) . ?
 S1 C1 1.765(2) . ?
 S1 C11 1.807(2) . ?
 N1 H1 0.85(4) . ?
 C1 C2 1.386(3) . ?
 C1 C6 1.384(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.393(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.391(3) . ?
 C4 C5 1.396(3) . ?
 C4 C7 1.535(3) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.391(3) . ?
 C6 H6 0.9500 . ?
 C7 C8 1.534(4) . ?
 C7 C9 1.528(4) . ?
 C7 C10 1.535(4) . ?
 C8 H8A 0.9800 . ?
 C8 H8B 0.9800 . ?
 C8 H8C 0.9800 . ?
 C9 H9A 0.9800 . ?
 C9 H9B 0.9800 . ?
 C9 H9C 0.9800 . ?
 C10 H10A 0.9800 . ?
 C10 H10B 0.9800 . ?
 C10 H10C 0.9800 . ?
 C11 H11A 0.9900 . ?
 C11 H11B 0.9900 . ?
 C11 C12 1.500(3) . ?
 C12 C13 1.382(3) . ?
 C12 C17 1.386(3) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.386(4) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.376(5) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.381(5) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.390(4) . ?
 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
 O1 S1 N1 121.68(11) . . ?
 O1 S1 C1 107.45(10) . . ?
 O1 S1 C11 103.06(10) . . ?
 N1 S1 C1 104.16(11) . . ?
 N1 S1 C11 112.79(11) . . ?
 C1 S1 C11 106.91(10) . . ?
 S1 N1 H1 112(2) . . ?
 C2 C1 S1 118.98(16) . . ?
 C6 C1 S1 120.30(16) . . ?
 C6 C1 C2 120.57(19) . . ?
 C1 C2 H2 120.4 . . ?
 C1 C2 C3 119.1(2) . . ?
 C3 C2 H2 120.4 . . ?
 C2 C3 H3 119.1 . . ?
 C4 C3 C2 121.9(2) . . ?
 C4 C3 H3 119.1 . . ?
 C3 C4 C5 117.3(2) . . ?
 C3 C4 C7 122.0(2) . . ?
 C5 C4 C7 120.4(2) . . ?
 C4 C5 H5 119.1 . . ?
 C6 C5 C4 121.8(2) . . ?
 C6 C5 H5 119.1 . . ?
 C1 C6 C5 119.2(2) . . ?
 C1 C6 H6 120.4 . . ?
 C5 C6 H6 120.4 . . ?
 C8 C7 C4 107.4(2) . . ?
 C8 C7 C10 108.7(2) . . ?
 C9 C7 C4 111.5(2) . . ?
 C9 C7 C8 107.7(3) . . ?
 C9 C7 C10 109.7(3) . . ?
 C10 C7 C4 111.8(2) . . ?
 C7 C8 H8A 109.5 . . ?
 C7 C8 H8B 109.5 . . ?
 C7 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?
 C7 C9 H9A 109.5 . . ?
 C7 C9 H9B 109.5 . . ?
 C7 C9 H9C 109.5 . . ?
 H9A C9 H9B 109.5 . . ?
 H9A C9 H9C 109.5 . . ?
 H9B C9 H9C 109.5 . . ?
 C7 C10 H10A 109.5 . . ?
 C7 C10 H10B 109.5 . . ?
 C7 C10 H10C 109.5 . . ?
 H10A C10 H10B 109.5 . . ?
 H10A C10 H10C 109.5 . . ?
 H10B C10 H10C 109.5 . . ?
 S1 C11 H11A 108.4 . . ?
 S1 C11 H11B 108.4 . . ?
 H11A C11 H11B 107.5 . . ?
 C12 C11 S1 115.47(15) . . ?
 C12 C11 H11A 108.4 . . ?
 C12 C11 H11B 108.4 . . ?
 C13 C12 C11 119.7(2) . . ?
 C13 C12 C17 119.0(2) . . ?
 C17 C12 C11 121.3(2) . . ?
 C12 C13 H13 119.7 . . ?
 C12 C13 C14 120.7(3) . . ?
 C14 C13 H13 119.7 . . ?
 C13 C14 H14 120.0 . . ?
 C15 C14 C13 120.0(3) . . ?
 C15 C14 H14 120.0 . . ?
 C14 C15 H15 120.0 . . ?
 C14 C15 C16 119.9(3) . . ?
 C16 C15 H15 120.0 . . ?
 C15 C16 H16 120.0 . . ?
 C15 C16 C17 120.0(3) . . ?
 C17 C16 H16 120.0 . . ?
 C12 C17 C16 120.4(3) . . ?
 C12 C17 H17 119.8 . . ?
 C16 C17 H17 119.8 . . ?

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
 S1 C1 C2 C3 -172.90(18) . . . . ?
 S1 C1 C6 C5 173.33(17) . . . . ?
 S1 C11 C12 C13 103.6(2) . . . . ?
 S1 C11 C12 C17 -78.4(2) . . . . ?
 O1 S1 C1 C2 27.8(2) . . . . ?
 O1 S1 C1 C6 -147.75(18) . . . . ?
 O1 S1 C11 C12 -176.21(17) . . . . ?
 N1 S1 C1 C2 158.14(18) . . . . ?
 N1 S1 C1 C6 -17.4(2) . . . . ?
 N1 S1 C11 C12 50.8(2) . . . . ?
 C1 S1 C11 C12 -63.12(19) . . . . ?
 C1 C2 C3 C4 -0.2(4) . . . . ?
 C2 C1 C6 C5 -2.2(3) . . . . ?
 C2 C3 C4 C5 -2.7(4) . . . . ?
 C2 C3 C4 C7 172.6(2) . . . . ?
 C3 C4 C5 C6 3.2(4) . . . . ?
 C3 C4 C7 C8 -91.9(3) . . . . ?
 C3 C4 C7 C9 25.8(4) . . . . ?
 C3 C4 C7 C10 149.0(3) . . . . ?
 C4 C5 C6 C1 -0.8(4) . . . . ?
 C5 C4 C7 C8 83.3(3) . . . . ?
 C5 C4 C7 C9 -159.0(3) . . . . ?
 C5 C4 C7 C10 -35.8(3) . . . . ?
 C6 C1 C2 C3 2.7(3) . . . . ?
 C7 C4 C5 C6 -172.2(2) . . . . ?
 C11 S1 C1 C2 -82.25(19) . . . . ?
 C11 S1 C1 C6 102.18(19) . . . . ?
 C11 C12 C13 C14 177.4(2) . . . . ?
 C11 C12 C17 C16 -177.3(2) . . . . ?
 C12 C13 C14 C15 0.0(4) . . . . ?
 C13 C12 C17 C16 0.8(4) . . . . ?
 C13 C14 C15 C16 0.7(5) . . . . ?
 C14 C15 C16 C17 -0.6(5) . . . . ?
 C15 C16 C17 C12 -0.1(4) . . . . ?
 C17 C12 C13 C14 -0.7(4) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
