data_exp_166
_audit_creation_date               2022-09-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_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 H18 N2 O2 S'
_chemical_formula_sum              'C17 H18 N2 O2 S'
_chemical_formula_weight           314.39
_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        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     9.3076(5)
_cell_length_b                     9.3243(5)
_cell_length_c                     10.1072(4)
_cell_angle_alpha                  102.086(4)
_cell_angle_beta                   102.480(4)
_cell_angle_gamma                  108.253(5)
_cell_volume                       776.19(7)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      4065
_cell_measurement_temperature      295(2)
_cell_measurement_theta_max        29.3010
_cell_measurement_theta_min        3.7890
_shelx_estimated_absorpt_T_max     0.954
_shelx_estimated_absorpt_T_min     0.901
_exptl_absorpt_coefficient_mu      0.217
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.71109
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.345
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               332
_exptl_crystal_size_max            0.49
_exptl_crystal_size_mid            0.38
_exptl_crystal_size_min            0.22
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0407
_diffrn_reflns_av_unetI/netI       0.0545
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.896
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -13
_diffrn_reflns_number              9437
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.896
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.500
_diffrn_reflns_theta_min           3.689
_diffrn_ambient_temperature        295(2)
_diffrn_detector_area_resol_mean   16.5253
_diffrn_detector_type              Sapphire3
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.896
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     18.00  94.00   1.00   20.00    --   21.29-153.00 -26.00   76
  2  ω     12.00  37.00   1.00   20.00    --   21.29-122.00 133.00   25
  3  ω    -61.00 -36.00   1.00   20.00    --  -22.85 122.00-144.00   25
  4  ω    -96.00 -18.00   1.00   20.00    --  -22.85 153.00  15.00   78
  5  ω    -45.00  40.00   1.00   20.00    --   21.29 -57.00-180.00   85
  6  ω    -90.00  -1.00   1.00   20.00    --  -22.85 -38.00   0.00   89
  7  ω      2.00  28.00   1.00   20.00    --   20.82  77.00-180.00   26
  8  ω    -39.00   5.00   1.00   20.00    --  -22.39 -77.00 -60.00   44
  9  ω    -48.00  45.00   1.00   20.00    --  -22.39  19.00   0.00   93
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'Xcalibur, Sapphire3'
_diffrn_measurement_method         'ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2973
_reflns_number_total               4252
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection         'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction          'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.288
_refine_diff_density_min           -0.547
_refine_diff_density_rms           0.057
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       208
_refine_ls_number_reflns           4252
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0837
_refine_ls_R_factor_gt             0.0596
_refine_ls_restrained_S_all        1.060
_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)+(0.0771P)²+0.1244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1470
_refine_ls_wR_factor_ref           0.1768
_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:
 C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C16(H16), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 0.34810(7) 0.48995(6) 0.65191(5) 0.04646(19) Uani 1 1 d . . . . .
 O2 O 0.0968(2) 0.6190(2) 0.40706(17) 0.0580(4) Uani 1 1 d . . . . .
 O1 O 0.2379(3) 0.5241(2) 1.13919(19) 0.0727(6) Uani 1 1 d . . . . .
 N1 N 0.2872(2) 0.5981(2) 0.89146(18) 0.0483(4) Uani 1 1 d . . . . .
 C4 C 0.3973(2) 0.7730(2) 0.6081(2) 0.0378(4) Uani 1 1 d . . . . .
 C3 C 0.3383(2) 0.7703(2) 0.7368(2) 0.0393(4) Uani 1 1 d . . . . .
 C12 C 0.5761(2) 0.8598(2) 0.6438(2) 0.0404(4) Uani 1 1 d . . . . .
 C2 C 0.3169(2) 0.6346(2) 0.7748(2) 0.0405(4) Uani 1 1 d . . . . .
 C6 C 0.1681(3) 0.5329(3) 0.4220(2) 0.0417(5) Uani 1 1 d . . . . .
 C5 C 0.3379(2) 0.5986(2) 0.5216(2) 0.0390(4) Uani 1 1 d . . . . .
 N2 N 0.2963(3) 1.0215(3) 0.8501(2) 0.0646(6) Uani 1 1 d . . . . .
 C1 C 0.3142(3) 0.9066(3) 0.8042(2) 0.0446(5) Uani 1 1 d . . . . .
 C13 C 0.6787(3) 0.9066(3) 0.7798(2) 0.0496(5) Uani 1 1 d . . . . .
 H13 H 0.639447 0.883485 0.853221 0.060 Uiso 1 1 calc R U . . .
 C17 C 0.6388(3) 0.8967(3) 0.5360(3) 0.0503(5) Uani 1 1 d . . . . .
 H17 H 0.571558 0.866469 0.443926 0.060 Uiso 1 1 calc R U . . .
 C7 C 0.0977(3) 0.3598(3) 0.3450(2) 0.0534(6) Uani 1 1 d . . . . .
 H7A H 0.051920 0.302682 0.404026 0.080 Uiso 1 1 calc R U . . .
 H7B H 0.179132 0.325657 0.322761 0.080 Uiso 1 1 calc R U . . .
 H7C H 0.016806 0.339911 0.258846 0.080 Uiso 1 1 calc R U . . .
 C8 C 0.2054(4) 0.4339(3) 0.8881(3) 0.0595(6) Uani 1 1 d . . . . .
 H8A H 0.228139 0.362427 0.818484 0.071 Uiso 1 1 calc R U . . .
 H8B H 0.091607 0.407641 0.860677 0.071 Uiso 1 1 calc R U . . .
 C16 C 0.7997(3) 0.9776(3) 0.5649(3) 0.0592(6) Uani 1 1 d . . . . .
 H16 H 0.839805 1.001181 0.492061 0.071 Uiso 1 1 calc R U . . .
 C10 C 0.2773(4) 0.7150(3) 1.0071(2) 0.0575(6) Uani 1 1 d . . . . .
 H10A H 0.169438 0.711652 0.988144 0.069 Uiso 1 1 calc R U . . .
 H10B H 0.346409 0.820232 1.013386 0.069 Uiso 1 1 calc R U . . .
 C14 C 0.8409(3) 0.9881(3) 0.8074(3) 0.0616(7) Uani 1 1 d . . . . .
 H14 H 0.909015 1.018893 0.899164 0.074 Uiso 1 1 calc R U . . .
 C9 C 0.2598(4) 0.4145(3) 1.0318(3) 0.0664(7) Uani 1 1 d . . . . .
 H9A H 0.200871 0.307582 1.030014 0.080 Uiso 1 1 calc R U . . .
 H9B H 0.371393 0.429972 1.054271 0.080 Uiso 1 1 calc R U . . .
 C15 C 0.9012(3) 1.0236(3) 0.7004(3) 0.0651(7) Uani 1 1 d . . . . .
 H15 H 1.009417 1.078040 0.719400 0.078 Uiso 1 1 calc R U . . .
 C11 C 0.3262(4) 0.6806(3) 1.1454(3) 0.0657(7) Uani 1 1 d . . . . .
 H11A H 0.438081 0.697427 1.169599 0.079 Uiso 1 1 calc R U . . .
 H11B H 0.311614 0.754006 1.219996 0.079 Uiso 1 1 calc R U . . .
 H5 H 0.406(2) 0.574(2) 0.463(2) 0.029(5) Uiso 1 1 d . . . . .
 H4 H 0.346(3) 0.823(3) 0.550(2) 0.039(5) 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 C2 1.774(2) . ?
 S1 C5 1.826(2) . ?
 O2 C6 1.204(3) . ?
 O1 C9 1.424(3) . ?
 O1 C11 1.413(4) . ?
 N1 C2 1.354(3) . ?
 N1 C8 1.470(3) . ?
 N1 C10 1.462(3) . ?
 C4 C3 1.519(3) . ?
 C4 C12 1.526(3) . ?
 C4 C5 1.532(3) . ?
 C4 H4 0.96(2) . ?
 C3 C2 1.366(3) . ?
 C3 C1 1.418(3) . ?
 C12 C13 1.383(3) . ?
 C12 C17 1.397(3) . ?
 C6 C5 1.528(3) . ?
 C6 C7 1.493(3) . ?
 C5 H5 1.004(19) . ?
 N2 C1 1.152(3) . ?
 C13 H13 0.9300 . ?
 C13 C14 1.395(3) . ?
 C17 H17 0.9300 . ?
 C17 C16 1.382(3) . ?
 C7 H7A 0.9600 . ?
 C7 H7B 0.9600 . ?
 C7 H7C 0.9600 . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C8 C9 1.499(3) . ?
 C16 H16 0.9300 . ?
 C16 C15 1.376(4) . ?
 C10 H10A 0.9700 . ?
 C10 H10B 0.9700 . ?
 C10 C11 1.506(3) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.374(4) . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C15 H15 0.9300 . ?
 C11 H11A 0.9700 . ?
 C11 H11B 0.9700 . ?

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
 C2 S1 C5 91.02(9) . . ?
 C11 O1 C9 110.0(2) . . ?
 C2 N1 C8 121.70(18) . . ?
 C2 N1 C10 121.16(19) . . ?
 C10 N1 C8 113.23(19) . . ?
 C3 C4 C12 114.36(16) . . ?
 C3 C4 C5 104.60(16) . . ?
 C3 C4 H4 109.8(13) . . ?
 C12 C4 C5 113.60(16) . . ?
 C12 C4 H4 107.5(14) . . ?
 C5 C4 H4 106.7(13) . . ?
 C2 C3 C4 114.78(17) . . ?
 C2 C3 C1 127.73(18) . . ?
 C1 C3 C4 117.48(17) . . ?
 C13 C12 C4 122.50(19) . . ?
 C13 C12 C17 118.5(2) . . ?
 C17 C12 C4 119.02(18) . . ?
 N1 C2 S1 116.59(16) . . ?
 N1 C2 C3 131.32(19) . . ?
 C3 C2 S1 111.93(14) . . ?
 O2 C6 C5 120.47(19) . . ?
 O2 C6 C7 122.5(2) . . ?
 C7 C6 C5 117.00(18) . . ?
 S1 C5 H5 106.3(11) . . ?
 C4 C5 S1 105.65(12) . . ?
 C4 C5 H5 114.2(11) . . ?
 C6 C5 S1 109.07(14) . . ?
 C6 C5 C4 114.39(16) . . ?
 C6 C5 H5 106.8(11) . . ?
 N2 C1 C3 174.7(2) . . ?
 C12 C13 H13 119.9 . . ?
 C12 C13 C14 120.3(2) . . ?
 C14 C13 H13 119.9 . . ?
 C12 C17 H17 119.7 . . ?
 C16 C17 C12 120.6(2) . . ?
 C16 C17 H17 119.7 . . ?
 C6 C7 H7A 109.5 . . ?
 C6 C7 H7B 109.5 . . ?
 C6 C7 H7C 109.5 . . ?
 H7A C7 H7B 109.5 . . ?
 H7A C7 H7C 109.5 . . ?
 H7B C7 H7C 109.5 . . ?
 N1 C8 H8A 109.7 . . ?
 N1 C8 H8B 109.7 . . ?
 N1 C8 C9 109.9(2) . . ?
 H8A C8 H8B 108.2 . . ?
 C9 C8 H8A 109.7 . . ?
 C9 C8 H8B 109.7 . . ?
 C17 C16 H16 119.7 . . ?
 C15 C16 C17 120.6(2) . . ?
 C15 C16 H16 119.7 . . ?
 N1 C10 H10A 109.7 . . ?
 N1 C10 H10B 109.7 . . ?
 N1 C10 C11 109.9(2) . . ?
 H10A C10 H10B 108.2 . . ?
 C11 C10 H10A 109.7 . . ?
 C11 C10 H10B 109.7 . . ?
 C13 C14 H14 119.6 . . ?
 C15 C14 C13 120.7(2) . . ?
 C15 C14 H14 119.6 . . ?
 O1 C9 C8 111.7(2) . . ?
 O1 C9 H9A 109.3 . . ?
 O1 C9 H9B 109.3 . . ?
 C8 C9 H9A 109.3 . . ?
 C8 C9 H9B 109.3 . . ?
 H9A C9 H9B 107.9 . . ?
 C16 C15 H15 120.3 . . ?
 C14 C15 C16 119.3(2) . . ?
 C14 C15 H15 120.3 . . ?
 O1 C11 C10 112.3(2) . . ?
 O1 C11 H11A 109.1 . . ?
 O1 C11 H11B 109.1 . . ?
 C10 C11 H11A 109.1 . . ?
 C10 C11 H11B 109.1 . . ?
 H11A C11 H11B 107.9 . . ?

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
 O2 C6 C5 S1 124.23(19) . . . . ?
 O2 C6 C5 C4 6.2(3) . . . . ?
 N1 C8 C9 O1 55.7(3) . . . . ?
 N1 C10 C11 O1 -54.6(3) . . . . ?
 C4 C3 C2 S1 -5.2(2) . . . . ?
 C4 C3 C2 N1 169.9(2) . . . . ?
 C4 C12 C13 C14 -178.9(2) . . . . ?
 C4 C12 C17 C16 178.9(2) . . . . ?
 C3 C4 C12 C13 11.2(3) . . . . ?
 C3 C4 C12 C17 -167.52(19) . . . . ?
 C3 C4 C5 S1 -35.13(17) . . . . ?
 C3 C4 C5 C6 84.84(19) . . . . ?
 C12 C4 C3 C2 -98.0(2) . . . . ?
 C12 C4 C3 C1 81.2(2) . . . . ?
 C12 C4 C5 S1 90.24(17) . . . . ?
 C12 C4 C5 C6 -149.79(17) . . . . ?
 C12 C13 C14 C15 0.1(4) . . . . ?
 C12 C17 C16 C15 -0.1(4) . . . . ?
 C2 S1 C5 C4 29.24(14) . . . . ?
 C2 S1 C5 C6 -94.16(15) . . . . ?
 C2 N1 C8 C9 150.7(2) . . . . ?
 C2 N1 C10 C11 -151.4(2) . . . . ?
 C5 S1 C2 N1 169.45(18) . . . . ?
 C5 S1 C2 C3 -14.68(17) . . . . ?
 C5 C4 C3 C2 26.9(2) . . . . ?
 C5 C4 C3 C1 -153.94(18) . . . . ?
 C5 C4 C12 C13 -108.8(2) . . . . ?
 C5 C4 C12 C17 72.5(2) . . . . ?
 C1 C3 C2 S1 175.78(18) . . . . ?
 C1 C3 C2 N1 -9.1(4) . . . . ?
 C13 C12 C17 C16 0.2(3) . . . . ?
 C13 C14 C15 C16 0.0(4) . . . . ?
 C17 C12 C13 C14 -0.2(3) . . . . ?
 C17 C16 C15 C14 0.0(4) . . . . ?
 C7 C6 C5 S1 -56.3(2) . . . . ?
 C7 C6 C5 C4 -174.32(18) . . . . ?
 C8 N1 C2 S1 -30.7(3) . . . . ?
 C8 N1 C2 C3 154.4(3) . . . . ?
 C8 N1 C10 C11 50.5(3) . . . . ?
 C10 N1 C2 S1 173.10(18) . . . . ?
 C10 N1 C2 C3 -1.8(4) . . . . ?
 C10 N1 C8 C9 -51.4(3) . . . . ?
 C9 O1 C11 C10 59.8(3) . . . . ?
 C11 O1 C9 C8 -60.4(3) . . . . ?


_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
;
