# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_12703
_audit_block_doi                 10.5517/ccdc.csd.cc2fgp8w
_database_code_depnum_ccdc_archive 'CCDC 2248438'
loop_
_audit_author_name
_audit_author_address
ZXXCCDC
;GXU
China
;
_audit_update_record             
;
2023-03-14 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_audit_creation_date             2023-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N3 S'
_chemical_formula_sum            'C19 H17 N3 S'
_chemical_formula_weight         319.41
_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                   7.7135(7)
_cell_length_b                   22.940(2)
_cell_length_c                   9.6284(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.290(11)
_cell_angle_gamma                90
_cell_volume                     1676.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.5690
_cell_measurement_theta_min      4.2940
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8754
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.440
_diffrn_reflns_theta_min         3.553
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  71.00   0.80    1.00    --   15.81  57.00 -60.00   90
  2  ω      2.00  63.60   0.80    1.00    --   15.81  57.00  60.00   77
  3  ω     36.00  80.00   0.80    1.00    --   15.81 178.00-120.00   55
  4  ω     40.00  68.80   0.80    1.00    --   15.81 178.00 -30.00   36
  5  ω    -24.00  11.20   0.80    1.00    --  -16.59 -99.00  60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127098000
_diffrn_orient_matrix_UB_12      0.0282096000
_diffrn_orient_matrix_UB_13      -0.0264702000
_diffrn_orient_matrix_UB_21      -0.0066481000
_diffrn_orient_matrix_UB_22      0.0122265000
_diffrn_orient_matrix_UB_23      0.0665081000
_diffrn_orient_matrix_UB_31      0.0924291000
_diffrn_orient_matrix_UB_32      -0.0030129000
_diffrn_orient_matrix_UB_33      0.0219624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2404
_reflns_number_total             3848
_reflns_odcompleteness_completeness 99.07
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.469
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0707
_refine_ls_restrained_S_all      1.041
_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)+(0.0754P)²+0.4195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1860
_refine_special_details          ?
_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:
 C15(H15), C9(H9), C12(H12), C19(H19), C11(H11), C5(H5), C16(H16), C18(H18),
 C3(H3), C17(H17), C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
;
_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 0.20251(10) 0.15985(4) 0.59148(8) 0.0670(3) Uani 1 1 d . . . . .
N1 N 0.6682(3) 0.31430(10) 0.3387(2) 0.0456(6) Uani 1 1 d . . . . .
N2 N 0.6600(3) 0.41916(10) 0.3140(3) 0.0495(6) Uani 1 1 d . . . . .
N3 N 0.8244(3) 0.43853(12) 0.3733(3) 0.0677(7) Uani 1 1 d . . . . .
C2 C 0.5925(3) 0.36750(12) 0.3607(3) 0.0447(6) Uani 1 1 d . . . . .
C14 C 0.0516(3) 0.13227(12) 0.4458(3) 0.0449(6) Uani 1 1 d . . . . .
C8 C 0.4388(3) 0.29916(13) 0.4477(3) 0.0455(7) Uani 1 1 d . . . . .
C15 C 0.0373(3) 0.15205(13) 0.3089(3) 0.0488(7) Uani 1 1 d . . . . .
H15 H 0.112335 0.181153 0.287584 0.059 Uiso 1 1 calc R . . . .
C13 C 0.5737(3) 0.27181(12) 0.3916(3) 0.0447(6) Uani 1 1 d . . . . .
C6 C 0.4513(3) 0.36067(13) 0.4269(3) 0.0494(7) Uani 1 1 d . . . . .
C9 C 0.3231(3) 0.26401(14) 0.5093(3) 0.0522(7) Uani 1 1 d . . . . .
H9 H 0.233337 0.281005 0.548277 0.063 Uiso 1 1 calc R . . . .
C12 C 0.5959(4) 0.21148(13) 0.3934(3) 0.0556(8) Uani 1 1 d . . . . .
H12 H 0.685725 0.194125 0.355246 0.067 Uiso 1 1 calc R . . . .
C19 C -0.0614(4) 0.08862(13) 0.4763(4) 0.0578(8) Uani 1 1 d . . . . .
H19 H -0.052311 0.074909 0.568176 0.069 Uiso 1 1 calc R . . . .
C10 C 0.3435(3) 0.20514(14) 0.5115(3) 0.0511(7) Uani 1 1 d . . . . .
C11 C 0.4806(4) 0.17872(14) 0.4535(3) 0.0580(8) Uani 1 1 d . . . . .
H11 H 0.492552 0.138377 0.456311 0.070 Uiso 1 1 calc R . . . .
C1 C 0.8190(4) 0.30454(14) 0.2687(4) 0.0597(8) Uani 1 1 d . . . . .
H1A H 0.852451 0.340687 0.230762 0.089 Uiso 1 1 calc GR . . . .
H1B H 0.787465 0.276884 0.193592 0.089 Uiso 1 1 calc GR . . . .
H1C H 0.915995 0.289626 0.335775 0.089 Uiso 1 1 calc GR . . . .
C5 C 0.5794(5) 0.45664(14) 0.2160(4) 0.0669(9) Uani 1 1 d . . . . .
H5 H 0.467406 0.452498 0.162001 0.080 Uiso 1 1 calc R . . . .
C16 C -0.0885(4) 0.12859(14) 0.2035(3) 0.0613(8) Uani 1 1 d . . . . .
H16 H -0.096734 0.141613 0.111072 0.074 Uiso 1 1 calc R . . . .
C18 C -0.1863(4) 0.06583(15) 0.3705(4) 0.0697(9) Uani 1 1 d . . . . .
H18 H -0.260844 0.036495 0.391288 0.084 Uiso 1 1 calc R . . . .
C3 C 0.8400(5) 0.48858(16) 0.3095(4) 0.0733(10) Uani 1 1 d . . . . .
H3 H 0.939102 0.512358 0.328597 0.088 Uiso 1 1 calc R . . . .
C17 C -0.2021(4) 0.08588(16) 0.2345(4) 0.0710(10) Uani 1 1 d . . . . .
H17 H -0.288592 0.070863 0.163852 0.085 Uiso 1 1 calc R . . . .
C4 C 0.6917(6) 0.50152(14) 0.2109(4) 0.0786(11) Uani 1 1 d . . . . .
H4 H 0.673045 0.534244 0.153141 0.094 Uiso 1 1 calc R . . . .
C7 C 0.3359(4) 0.40683(16) 0.4690(4) 0.0774(11) Uani 1 1 d . . . . .
H7A H 0.378403 0.444396 0.446649 0.116 Uiso 1 1 calc GR . . . .
H7B H 0.336846 0.404428 0.568641 0.116 Uiso 1 1 calc GR . . . .
H7C H 0.217732 0.401498 0.418758 0.116 Uiso 1 1 calc GR . . . .


_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 C14 1.772(3) . ?
S1 C10 1.776(3) . ?
N1 C2 1.386(3) . ?
N1 C13 1.369(3) . ?
N1 C1 1.461(3) . ?
N2 N3 1.368(3) . ?
N2 C2 1.401(3) . ?
N2 C5 1.344(4) . ?
N3 C3 1.318(4) . ?
C2 C6 1.365(4) . ?
C14 C15 1.380(4) . ?
C14 C19 1.393(4) . ?
C8 C13 1.403(4) . ?
C8 C6 1.431(4) . ?
C8 C9 1.410(4) . ?
C15 C16 1.382(4) . ?
C13 C12 1.394(4) . ?
C6 C7 1.486(4) . ?
C9 C10 1.359(4) . ?
C12 C11 1.368(4) . ?
C19 C18 1.374(4) . ?
C10 C11 1.418(4) . ?
C5 C4 1.352(5) . ?
C16 C17 1.382(4) . ?
C18 C17 1.372(5) . ?
C3 C4 1.382(5) . ?

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
C14 S1 C10 103.42(13) . . ?
C2 N1 C1 126.7(2) . . ?
C13 N1 C2 107.6(2) . . ?
C13 N1 C1 125.7(2) . . ?
N3 N2 C2 120.7(2) . . ?
C5 N2 N3 111.3(3) . . ?
C5 N2 C2 127.9(3) . . ?
C3 N3 N2 104.1(3) . . ?
N1 C2 N2 120.3(2) . . ?
C6 C2 N1 111.3(2) . . ?
C6 C2 N2 128.4(3) . . ?
C15 C14 S1 124.6(2) . . ?
C15 C14 C19 119.4(3) . . ?
C19 C14 S1 115.9(2) . . ?
C13 C8 C6 108.3(2) . . ?
C13 C8 C9 118.4(3) . . ?
C9 C8 C6 133.4(3) . . ?
C14 C15 C16 120.0(3) . . ?
N1 C13 C8 107.8(2) . . ?
N1 C13 C12 129.7(2) . . ?
C12 C13 C8 122.4(3) . . ?
C2 C6 C8 104.9(2) . . ?
C2 C6 C7 127.8(3) . . ?
C8 C6 C7 127.3(3) . . ?
C10 C9 C8 119.6(3) . . ?
C11 C12 C13 117.6(3) . . ?
C18 C19 C14 120.0(3) . . ?
C9 C10 S1 120.7(2) . . ?
C9 C10 C11 120.7(3) . . ?
C11 C10 S1 118.6(2) . . ?
C12 C11 C10 121.2(3) . . ?
N2 C5 C4 107.1(3) . . ?
C15 C16 C17 120.4(3) . . ?
C17 C18 C19 120.7(3) . . ?
N3 C3 C4 111.9(3) . . ?
C18 C17 C16 119.5(3) . . ?
C5 C4 C3 105.6(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.577
_oxdiff_exptl_absorpt_empirical_full_min 0.658
