# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_21201000801-738
_database_code_depnum_ccdc_archive 'CCDC 2099149'
loop_
_audit_author_name
_audit_author_address
'Mari Carmen Torralba'
;Universidad Complutense de Madrid
Spain
;
_audit_update_record             
;
2021-07-25 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N3 O2 S'
_chemical_formula_sum            'C19 H15 N3 O2 S'
_chemical_formula_weight         349.40
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5191(2)
_cell_length_b                   10.3297(2)
_cell_length_c                   18.8853(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.6638(8)
_cell_angle_gamma                90
_cell_volume                     1650.67(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      4.71
_shelx_estimated_absorpt_T_max   0.739
_shelx_estimated_absorpt_T_min   0.422
_exptl_absorpt_coefficient_mu    1.894
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4842
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36441
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.188
_diffrn_reflns_theta_min         4.715
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3030
_reflns_number_total             3269
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.061
_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)+(0.0748P)²+0.6319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1324
_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:
 C21(H21), C15(H15), C18(H18), C20(H20), C11(H11), C17(H17), C12(H12),
 C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S4 S 0.30101(5) 0.30849(5) 0.12790(3) 0.04981(18) Uani 1 1 d . . . . .
N7 N 0.12252(17) 0.50410(13) 0.11067(7) 0.0395(3) Uani 1 1 d . . . . .
O2 O 0.17009(19) 1.00262(15) -0.18438(8) 0.0590(4) Uani 1 1 d . . . . .
N3 N 0.27392(19) 0.51032(16) 0.02493(8) 0.0476(4) Uani 1 1 d . . . . .
C8 C 0.2397(2) 0.44616(18) 0.08116(9) 0.0432(4) Uani 1 1 d . . . . .
C16 C 0.1648(2) 0.71487(18) -0.03098(9) 0.0431(4) Uani 1 1 d . . . . .
O1 O 0.2146(2) 0.13762(15) 0.23655(8) 0.0669(4) Uani 1 1 d . . . . .
C21 C 0.0551(2) 0.81445(19) -0.03335(10) 0.0494(4) Uani 1 1 d . . . . .
H21 H -0.018487 0.815178 -0.000605 0.059 Uiso 1 1 calc R . . . .
C5 C 0.1595(2) 0.34031(17) 0.18805(9) 0.0412(4) Uani 1 1 d . . . . .
C19 C 0.1615(2) 0.91186(19) -0.13258(9) 0.0464(4) Uani 1 1 d . . . . .
C9 C 0.1534(2) 0.24280(18) 0.24392(10) 0.0451(4) Uani 1 1 d . . . . .
C2 C 0.1697(2) 0.61230(18) 0.02310(9) 0.0435(4) Uani 1 1 d . . . . .
C6 C 0.0725(2) 0.44725(17) 0.17069(9) 0.0394(4) Uani 1 1 d . . . . .
C15 C 0.1053(2) 0.38858(19) 0.34554(10) 0.0503(4) Uani 1 1 d . . . . .
H15 H 0.164626 0.453151 0.326953 0.060 Uiso 1 1 calc R . . . .
C18 C 0.2715(2) 0.8124(2) -0.13052(11) 0.0526(5) Uani 1 1 d . . . . .
H18 H 0.344765 0.811440 -0.163389 0.063 Uiso 1 1 calc R . . . .
C10 C 0.0787(2) 0.27202(17) 0.30956(9) 0.0421(4) Uani 1 1 d . . . . .
C20 C 0.0524(2) 0.9131(2) -0.08349(10) 0.0498(4) Uani 1 1 d . . . . .
H20 H -0.021790 0.979334 -0.084118 0.060 Uiso 1 1 calc R . . . .
C11 C -0.0108(3) 0.1765(2) 0.33776(11) 0.0545(5) Uani 1 1 d . . . . .
H11 H -0.027814 0.097763 0.314276 0.065 Uiso 1 1 calc R . . . .
C17 C 0.2738(2) 0.7153(2) -0.08057(10) 0.0500(4) Uani 1 1 d . . . . .
H17 H 0.348525 0.649539 -0.079900 0.060 Uiso 1 1 calc R . . . .
C12 C -0.0747(3) 0.1987(2) 0.40069(12) 0.0654(6) Uani 1 1 d . . . . .
H12 H -0.135932 0.135302 0.419154 0.079 Uiso 1 1 calc R . . . .
C13 C -0.0476(3) 0.3142(2) 0.43595(12) 0.0663(6) Uani 1 1 d . . . . .
H13 H -0.090837 0.329008 0.478231 0.080 Uiso 1 1 calc R . . . .
C14 C 0.0434(3) 0.4082(2) 0.40894(11) 0.0623(6) Uani 1 1 d . . . . .
H14 H 0.063168 0.485465 0.433636 0.075 Uiso 1 1 calc R . . . .
C22 C 0.0682(3) 1.1112(2) -0.18565(14) 0.0690(6) Uani 1 1 d . . . . .
H22A H 0.090317 1.169060 -0.223009 0.103 Uiso 1 1 calc GR . . . .
H22B H 0.084850 1.155277 -0.140664 0.103 Uiso 1 1 calc GR . . . .
H22C H -0.039636 1.082749 -0.194149 0.103 Uiso 1 1 calc GR . . . .
N1 N 0.07410(18) 0.61413(15) 0.07394(8) 0.0437(3) Uani 1 1 d . . . . .
C23 C -0.0582(2) 0.50517(17) 0.20021(9) 0.0434(4) Uani 1 1 d . . . . .
H23A H -0.022407 0.579934 0.227658 0.065 Uiso 1 1 calc GR . . . .
H23B H -0.102678 0.443747 0.230418 0.065 Uiso 1 1 calc GR . . . .
H23C H -0.137161 0.530621 0.162325 0.065 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
S4 C8 1.7226(19) . ?
S4 C5 1.7804(17) . ?
N7 C8 1.339(2) . ?
N7 C6 1.387(2) . ?
N7 N1 1.370(2) . ?
O2 C19 1.363(2) . ?
O2 C22 1.417(3) . ?
N3 C8 1.313(2) . ?
N3 C2 1.375(2) . ?
C16 C21 1.387(3) . ?
C16 C2 1.469(3) . ?
C16 C17 1.393(3) . ?
O1 C9 1.220(2) . ?
C21 C20 1.390(3) . ?
C5 C9 1.464(3) . ?
C5 C6 1.349(3) . ?
C19 C18 1.388(3) . ?
C19 C20 1.387(3) . ?
C9 C10 1.488(3) . ?
C2 N1 1.329(2) . ?
C6 C23 1.433(2) . ?
C15 C10 1.388(3) . ?
C15 C14 1.378(3) . ?
C18 C17 1.376(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.382(3) . ?
C12 C13 1.373(4) . ?
C13 C14 1.377(3) . ?

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 S4 C5 89.25(8) . . ?
C8 N7 C6 117.73(15) . . ?
C8 N7 N1 110.80(14) . . ?
N1 N7 C6 131.46(14) . . ?
C19 O2 C22 118.21(16) . . ?
C8 N3 C2 101.75(15) . . ?
N7 C8 S4 110.61(13) . . ?
N3 C8 S4 138.46(14) . . ?
N3 C8 N7 110.93(16) . . ?
C21 C16 C2 121.46(16) . . ?
C21 C16 C17 118.38(17) . . ?
C17 C16 C2 120.15(18) . . ?
C16 C21 C20 121.58(17) . . ?
C9 C5 S4 114.59(13) . . ?
C6 C5 S4 112.93(13) . . ?
C6 C5 C9 132.37(16) . . ?
O2 C19 C18 115.90(16) . . ?
O2 C19 C20 124.69(19) . . ?
C20 C19 C18 119.41(17) . . ?
O1 C9 C5 118.63(17) . . ?
O1 C9 C10 120.35(17) . . ?
C5 C9 C10 121.00(15) . . ?
N3 C2 C16 122.42(16) . . ?
N1 C2 N3 116.14(16) . . ?
N1 C2 C16 121.44(17) . . ?
N7 C6 C23 117.88(15) . . ?
C5 C6 N7 109.45(15) . . ?
C5 C6 C23 132.62(16) . . ?
C14 C15 C10 119.72(19) . . ?
C17 C18 C19 120.98(17) . . ?
C15 C10 C9 121.49(17) . . ?
C15 C10 C11 119.56(18) . . ?
C11 C10 C9 118.80(17) . . ?
C19 C20 C21 119.28(19) . . ?
C12 C11 C10 120.0(2) . . ?
C18 C17 C16 120.38(19) . . ?
C13 C12 C11 120.0(2) . . ?
C12 C13 C14 120.2(2) . . ?
C13 C14 C15 120.5(2) . . ?
C2 N1 N7 100.38(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'


#============================================================================END

