data_a01
_audit_creation_date               2020-06-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_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           'C14 H12 N2 S'
_chemical_formula_sum              'C14 H12 N2 S'
_chemical_formula_weight           240.32
_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'
 '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                     13.162(4)
_cell_length_b                     7.262(2)
_cell_length_c                     13.191(4)
_cell_angle_alpha                  90
_cell_angle_beta                   109.170(4)
_cell_angle_gamma                  90
_cell_volume                       1191.0(7)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1956
_cell_measurement_temperature      296.15
_cell_measurement_theta_max        25.268
_cell_measurement_theta_min        2.805
_shelx_estimated_absorpt_T_max     0.973
_shelx_estimated_absorpt_T_min     0.971
_exptl_absorpt_coefficient_mu      0.248
_exptl_absorpt_correction_T_max    0.973
_exptl_absorpt_correction_T_min    0.971
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS (Bruker, 2005)'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              brown
_exptl_crystal_density_diffrn      1.340
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               504
_exptl_crystal_size_max            0.12
_exptl_crystal_size_mid            0.12
_exptl_crystal_size_min            0.11
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0199
_diffrn_reflns_av_unetI/netI       0.0229
_diffrn_reflns_Laue_measured_fraction_full  0.961
_diffrn_reflns_Laue_measured_fraction_max  0.961
_diffrn_reflns_limit_h_max         14
_diffrn_reflns_limit_h_min         -14
_diffrn_reflns_limit_k_max         8
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         10
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              5136
_diffrn_reflns_point_group_measured_fraction_full  0.961
_diffrn_reflns_point_group_measured_fraction_max  0.961
_diffrn_reflns_theta_full          24.386
_diffrn_reflns_theta_max           24.386
_diffrn_reflns_theta_min           1.638
_diffrn_ambient_temperature        296.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.961
_diffrn_measured_fraction_theta_max  0.961
_diffrn_measurement_device_type    'Bruker P4'
_diffrn_measurement_method         'ω scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_source_current             30.0
_diffrn_source_power               1.35
_diffrn_source_voltage             45.0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1565
_reflns_number_total               1889
_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 v7.68A (Bruker, 2009)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v7.68A (Bruker, 2009)'
_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           0.198
_refine_diff_density_min           -0.185
_refine_diff_density_rms           0.037
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.079
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       160
_refine_ls_number_reflns           1889
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0465
_refine_ls_R_factor_gt             0.0374
_refine_ls_restrained_S_all        1.079
_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)+(0.0632P)²+0.2574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1106
_refine_ls_wR_factor_ref           0.1165
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.12382(5) 0.57169(8) 0.48491(4) 0.0588(2) Uani 1 1 d . . . . .
 N1 N 0.29242(15) 0.4622(2) 0.44221(13) 0.0497(5) Uani 1 1 d . . . . .
 N2 N 0.47952(19) 0.3634(3) 0.59509(17) 0.0638(6) Uani 1 1 d . . . . .
 H2A H 0.437329 0.382526 0.530628 0.077 Uiso 1 1 d R U . . .
 C1 C 0.25768(17) 0.4948(3) 0.52260(16) 0.0445(5) Uani 1 1 d . . . . .
 C2 C 0.42685(17) 0.3996(3) 0.66686(16) 0.0477(5) Uani 1 1 d . . . . .
 C3 C 0.32067(17) 0.4678(2) 0.63544(16) 0.0442(5) Uani 1 1 d . . . . .
 C4 C 0.27513(18) 0.5076(3) 0.71557(16) 0.0499(5) Uani 1 1 d . . . . .
 H4 H 0.205741 0.555302 0.695100 0.060 Uiso 1 1 calc R U . . .
 C5 C 0.21256(18) 0.4952(3) 0.34482(16) 0.0489(5) Uani 1 1 d . . . . .
 C6 C 0.48061(18) 0.3696(3) 0.77643(16) 0.0542(6) Uani 1 1 d . . . . .
 H6 H 0.550131 0.322383 0.798435 0.065 Uiso 1 1 calc R U . . .
 C7 C 0.43260(19) 0.4086(3) 0.85167(17) 0.0543(6) Uani 1 1 d . . . . .
 H7 H 0.470496 0.387264 0.923727 0.065 Uiso 1 1 calc R U . . .
 C8 C 0.11570(19) 0.5576(3) 0.35179(17) 0.0527(6) Uani 1 1 d . . . . .
 C9 C 0.32906(19) 0.4790(3) 0.82340(17) 0.0522(6) Uani 1 1 d . . . . .
 C10 C 0.2253(2) 0.4714(3) 0.24427(18) 0.0628(6) Uani 1 1 d . . . . .
 H10 H 0.289569 0.428046 0.238362 0.075 Uiso 1 1 calc R U . . .
 C11 C 0.0289(2) 0.6021(3) 0.2592(2) 0.0670(7) Uani 1 1 d . . . . .
 H11 H -0.035980 0.645341 0.263752 0.080 Uiso 1 1 calc R U . . .
 C12 C 0.1397(2) 0.5142(4) 0.1546(2) 0.0704(7) Uani 1 1 d . . . . .
 H12 H 0.146598 0.499035 0.087191 0.084 Uiso 1 1 calc R U . . .
 C13 C 0.2767(2) 0.5192(3) 0.90747(19) 0.0675(7) Uani 1 1 d . . . . .
 H13A H 0.313475 0.619478 0.951846 0.101 Uiso 1 1 calc R U . . .
 H13B H 0.280756 0.411789 0.951076 0.101 Uiso 1 1 calc R U . . .
 H13C H 0.202683 0.551689 0.872796 0.101 Uiso 1 1 calc R U . . .
 C14 C 0.0441(2) 0.5789(3) 0.1618(2) 0.0736(8) Uani 1 1 d . . . . .
 H14 H -0.011602 0.607685 0.099206 0.088 Uiso 1 1 calc R U . . .
 H2B H 0.538(2) 0.328(4) 0.618(2) 0.082(9) 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 1.757(2) . ?
 S1 C8 1.727(2) . ?
 N1 C1 1.307(3) . ?
 N1 C5 1.388(3) . ?
 N2 H2A 0.8606 . ?
 N2 C2 1.370(3) . ?
 N2 H2B 0.78(3) . ?
 C1 C3 1.460(3) . ?
 C2 C3 1.411(3) . ?
 C2 C6 1.402(3) . ?
 C3 C4 1.406(3) . ?
 C4 H4 0.9300 . ?
 C4 C9 1.381(3) . ?
 C5 C8 1.384(3) . ?
 C5 C10 1.401(3) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.370(3) . ?
 C7 H7 0.9300 . ?
 C7 C9 1.387(3) . ?
 C8 C11 1.409(3) . ?
 C9 C13 1.514(3) . ?
 C10 H10 0.9300 . ?
 C10 C12 1.375(4) . ?
 C11 H11 0.9300 . ?
 C11 C14 1.374(4) . ?
 C12 H12 0.9300 . ?
 C12 C14 1.375(4) . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?
 C14 H14 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
 C8 S1 C1 89.45(10) . . ?
 C1 N1 C5 111.08(18) . . ?
 H2A N2 H2B 132.5 . . ?
 C2 N2 H2A 110.1 . . ?
 C2 N2 H2B 117(2) . . ?
 N1 C1 S1 114.41(15) . . ?
 N1 C1 C3 124.8(2) . . ?
 C3 C1 S1 120.80(15) . . ?
 N2 C2 C3 122.8(2) . . ?
 N2 C2 C6 118.9(2) . . ?
 C6 C2 C3 118.2(2) . . ?
 C2 C3 C1 121.52(19) . . ?
 C4 C3 C1 120.0(2) . . ?
 C4 C3 C2 118.51(19) . . ?
 C3 C4 H4 118.6 . . ?
 C9 C4 C3 122.8(2) . . ?
 C9 C4 H4 118.6 . . ?
 N1 C5 C10 124.4(2) . . ?
 C8 C5 N1 115.41(19) . . ?
 C8 C5 C10 120.1(2) . . ?
 C2 C6 H6 119.4 . . ?
 C7 C6 C2 121.2(2) . . ?
 C7 C6 H6 119.4 . . ?
 C6 C7 H7 119.1 . . ?
 C6 C7 C9 121.8(2) . . ?
 C9 C7 H7 119.1 . . ?
 C5 C8 S1 109.64(16) . . ?
 C5 C8 C11 121.3(2) . . ?
 C11 C8 S1 129.0(2) . . ?
 C4 C9 C7 117.4(2) . . ?
 C4 C9 C13 121.4(2) . . ?
 C7 C9 C13 121.2(2) . . ?
 C5 C10 H10 121.1 . . ?
 C12 C10 C5 117.9(3) . . ?
 C12 C10 H10 121.1 . . ?
 C8 C11 H11 121.4 . . ?
 C14 C11 C8 117.2(3) . . ?
 C14 C11 H11 121.4 . . ?
 C10 C12 H12 119.1 . . ?
 C10 C12 C14 121.9(3) . . ?
 C14 C12 H12 119.1 . . ?
 C9 C13 H13A 109.5 . . ?
 C9 C13 H13B 109.5 . . ?
 C9 C13 H13C 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?
 C11 C14 C12 121.6(2) . . ?
 C11 C14 H14 119.2 . . ?
 C12 C14 H14 119.2 . . ?

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 C3 C2 177.60(15) . . . . ?
 S1 C1 C3 C4 -1.5(3) . . . . ?
 S1 C8 C11 C14 179.58(17) . . . . ?
 N1 C1 C3 C2 -1.0(3) . . . . ?
 N1 C1 C3 C4 179.90(18) . . . . ?
 N1 C5 C8 S1 -1.1(2) . . . . ?
 N1 C5 C8 C11 177.94(19) . . . . ?
 N1 C5 C10 C12 -178.3(2) . . . . ?
 N2 C2 C3 C1 3.4(3) . . . . ?
 N2 C2 C3 C4 -177.48(19) . . . . ?
 N2 C2 C6 C7 178.1(2) . . . . ?
 C1 S1 C8 C5 0.55(15) . . . . ?
 C1 S1 C8 C11 -178.4(2) . . . . ?
 C1 N1 C5 C8 1.2(3) . . . . ?
 C1 N1 C5 C10 -179.55(19) . . . . ?
 C1 C3 C4 C9 177.64(18) . . . . ?
 C2 C3 C4 C9 -1.5(3) . . . . ?
 C2 C6 C7 C9 0.1(3) . . . . ?
 C3 C2 C6 C7 -1.3(3) . . . . ?
 C3 C4 C9 C7 0.3(3) . . . . ?
 C3 C4 C9 C13 -178.54(19) . . . . ?
 C5 N1 C1 S1 -0.8(2) . . . . ?
 C5 N1 C1 C3 177.93(18) . . . . ?
 C5 C8 C11 C14 0.7(3) . . . . ?
 C5 C10 C12 C14 0.2(4) . . . . ?
 C6 C2 C3 C1 -177.19(18) . . . . ?
 C6 C2 C3 C4 1.9(3) . . . . ?
 C6 C7 C9 C4 0.4(3) . . . . ?
 C6 C7 C9 C13 179.3(2) . . . . ?
 C8 S1 C1 N1 0.13(16) . . . . ?
 C8 S1 C1 C3 -178.62(16) . . . . ?
 C8 C5 C10 C12 0.9(3) . . . . ?
 C8 C11 C14 C12 0.3(4) . . . . ?
 C10 C5 C8 S1 179.62(16) . . . . ?
 C10 C5 C8 C11 -1.3(3) . . . . ?
 C10 C12 C14 C11 -0.8(4) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
