# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_cyg337m
_database_code_depnum_ccdc_archive 'CCDC 2025922'
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-12-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         296.38

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   15.2607(10)
_cell_length_b                   6.7396(4)
_cell_length_c                   15.8960(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.082(2)
_cell_angle_gamma                90
_cell_volume                     1480.75(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3806
_cell_measurement_theta_min      2.4372
_cell_measurement_theta_max      28.4395
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            23145
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         29.70
_diffrn_reflns_theta_full        29.70
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             4192
_reflns_number_gt                3065
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.1158
_refine_ls_wR_factor_gt          0.2387
_refine_ls_wR_factor_ref         0.2519
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.200
_refine_ls_number_reflns         4192
_refine_ls_number_parameters     243
_refine_ls_number_restraints     351
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.5710P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.586
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2375(3) 0.2592(9) 0.3466(4) 0.0294(11) Uani d . . . 1.0 . .
H H1A 0.251244 0.138783 0.384625 0.044 Uiso calc U . R 1.0 . .
H H1B 0.170389 0.255521 0.299345 0.044 Uiso calc U . R 1.0 . .
H H1C 0.246832 0.375927 0.386236 0.044 Uiso calc U . R 1.0 . .
C C2 0.4313(3) 0.2611(7) 0.3853(3) 0.0202(9) Uani d . . . 1.0 . .
C C3 0.5264(4) 0.2311(8) 0.5431(3) 0.0254(10) Uani d . . . 1.0 . .
C C4 0.6146(3) 0.2480(7) 0.5249(3) 0.0238(10) Uani d . . D 1.0 . .
H H4C 0.637644 0.112452 0.521078 0.029 Uiso calc U P R 0.534(8) A 2
H H4D 0.665965 0.314466 0.578815 0.029 Uiso calc U P R 0.534(8) A 2
H H4A 0.635693 0.388362 0.532637 0.029 Uiso calc U P R 0.466(8) A 1
H H4B 0.667244 0.169072 0.572081 0.029 Uiso calc U P R 0.466(8) A 1
C C5 0.6005(5) 0.1802(14) 0.4313(5) 0.0221(19) Uani d U P D 0.466(8) A 1
H H5 0.595895 0.032261 0.426585 0.027 Uiso calc U P R 0.466(8) A 1
C C6 0.6803(5) 0.2562(13) 0.4074(6) 0.0270(18) Uani d U P DG 0.466(8) A 1
C C7 0.7243(7) 0.1242(10) 0.3700(8) 0.032(2) Uani d U P DG 0.466(8) A 1
H H7 0.705904 -0.011612 0.362526 0.039 Uiso calc U P R 0.466(8) A 1
C C8 0.7951(7) 0.1910(14) 0.3436(8) 0.032(2) Uani d U P DG 0.466(8) A 1
H H8 0.825185 0.1008 0.318111 0.039 Uiso calc U P R 0.466(8) A 1
C C9 0.8220(6) 0.3898(16) 0.3546(7) 0.035(2) Uani d U P DG 0.466(8) A 1
H H9 0.8704 0.435389 0.336552 0.042 Uiso calc U P R 0.466(8) A 1
C C10 0.7780(7) 0.5217(11) 0.3919(7) 0.035(2) Uani d U P DG 0.466(8) A 1
H H10 0.796334 0.657569 0.399407 0.042 Uiso calc U P R 0.466(8) A 1
C C11 0.7071(6) 0.4550(12) 0.4183(6) 0.0308(19) Uani d U P DG 0.466(8) A 1
H H11 0.677053 0.54516 0.443823 0.037 Uiso calc U P R 0.466(8) A 1
C C5A 0.6018(5) 0.3605(13) 0.4372(5) 0.0215(16) Uani d U P D 0.534(8) A 2
H H5A 0.592001 0.504106 0.446544 0.026 Uiso calc U P R 0.534(8) A 2
C C6A 0.6824(6) 0.3432(14) 0.4061(7) 0.0251(16) Uani d U P D 0.534(8) A 2
C C7A 0.7077(7) 0.1615(15) 0.3816(9) 0.031(2) Uani d U P D 0.534(8) A 2
H H7A 0.67492 0.044774 0.385788 0.037 Uiso calc U P R 0.534(8) A 2
C C8A 0.7807(8) 0.1477(16) 0.3508(9) 0.035(2) Uani d U P D 0.534(8) A 2
H H8A 0.797774 0.022666 0.334618 0.042 Uiso calc U P R 0.534(8) A 2
C C9A 0.8279(8) 0.3189(16) 0.3443(8) 0.032(2) Uani d U P D 0.534(8) A 2
H H9A 0.875586 0.312051 0.320791 0.039 Uiso calc U P R 0.534(8) A 2
C C10A 0.8055(7) 0.4999(16) 0.3719(8) 0.034(2) Uani d U P D 0.534(8) A 2
H H10A 0.840179 0.615714 0.370026 0.041 Uiso calc U P R 0.534(8) A 2
C C11A 0.7327(7) 0.5126(14) 0.4023(7) 0.0308(18) Uani d U P D 0.534(8) A 2
H H11A 0.717262 0.637151 0.420475 0.037 Uiso calc U P R 0.534(8) A 2
C C12 0.4901(3) 0.2914(8) 0.2668(3) 0.0242(10) Uani d . . . 1.0 . .
C C13 0.4728(4) 0.1211(9) 0.2136(4) 0.0303(12) Uani d . . . 1.0 . .
H H13 0.472779 -0.00519 0.240181 0.036 Uiso calc U . R 1.0 . .
C C14 0.4557(4) 0.1373(10) 0.1211(4) 0.0352(13) Uani d . . . 1.0 . .
H H14 0.443963 0.021494 0.083809 0.042 Uiso calc U . R 1.0 . .
C C15 0.4557(4) 0.3225(11) 0.0826(4) 0.0372(14) Uani d . . . 1.0 . .
H H15 0.443436 0.333098 0.018948 0.045 Uiso calc U . R 1.0 . .
C C16 0.4733(4) 0.4898(10) 0.1362(4) 0.0346(13) Uani d . . . 1.0 . .
H H16 0.473883 0.61573 0.109643 0.042 Uiso calc U . R 1.0 . .
C C17 0.4904(4) 0.4771(9) 0.2297(4) 0.0285(11) Uani d . . . 1.0 . .
H H17 0.502068 0.593057 0.266805 0.034 Uiso calc U . R 1.0 . .
N N1 0.5068(3) 0.2774(7) 0.3626(3) 0.0244(9) Uani d . . D 1.0 . .
N N2 0.4365(3) 0.2407(8) 0.4700(3) 0.0272(9) Uani d . . . 1.0 . .
O O1 0.5332(3) 0.2103(6) 0.6226(2) 0.0307(9) Uani d . . . 1.0 . .
S S1 0.31735(8) 0.2725(2) 0.29117(9) 0.0253(3) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 S1 . 1.784(5) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 N2 . 1.323(6) ?
C2 N1 . 1.350(6) ?
C2 S1 . 1.750(5) ?
C3 O1 . 1.230(6) ?
C3 N2 . 1.373(6) ?
C3 C4 . 1.497(7) ?
C4 C5 . 1.483(9) ?
C4 C5A . 1.524(8) ?
C4 H4C . 0.99 ?
C4 H4D . 0.99 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.510(8) ?
C5 N1 . 1.531(8) ?
C5 H5 . 1.0 ?
C6 C7 . 1.39 ?
C6 C11 . 1.39 ?
C7 C8 . 1.39 ?
C7 H7 . 0.95 ?
C8 C9 . 1.39 ?
C8 H8 . 0.95 ?
C9 C10 . 1.39 ?
C9 H9 . 0.95 ?
C10 C11 . 1.39 ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
C5A C6A . 1.513(9) ?
C5A N1 . 1.538(8) ?
C5A H5A . 1.0 ?
C6A C7A . 1.389(8) ?
C6A C11A . 1.391(8) ?
C7A C8A . 1.395(8) ?
C7A H7A . 0.95 ?
C8A C9A . 1.387(8) ?
C8A H8A . 0.95 ?
C9A C10A . 1.387(8) ?
C9A H9A . 0.95 ?
C10A C11A . 1.389(8) ?
C10A H10A . 0.95 ?
C11A H11A . 0.95 ?
C12 C13 . 1.383(8) ?
C12 C17 . 1.385(8) ?
C12 N1 . 1.435(6) ?
C13 C14 . 1.385(8) ?
C13 H13 . 0.95 ?
C14 C15 . 1.390(9) ?
C14 H14 . 0.95 ?
C15 C16 . 1.370(9) ?
C15 H15 . 0.95 ?
C16 C17 . 1.397(7) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S1 C1 H1A . . 109.5 ?
S1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
S1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N2 C2 N1 . . 126.2(4) ?
N2 C2 S1 . . 119.0(3) ?
N1 C2 S1 . . 114.8(3) ?
O1 C3 N2 . . 119.6(5) ?
O1 C3 C4 . . 121.0(4) ?
N2 C3 C4 . . 119.4(4) ?
C5 C4 C3 . . 114.3(5) ?
C3 C4 C5A . . 115.9(4) ?
C3 C4 H4C . . 108.3 ?
C5A C4 H4C . . 108.3 ?
C3 C4 H4D . . 108.3 ?
C5A C4 H4D . . 108.3 ?
H4C C4 H4D . . 107.4 ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4B . . 108.7 ?
C3 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
C4 C5 C6 . . 111.0(6) ?
C4 C5 N1 . . 106.2(5) ?
C6 C5 N1 . . 106.5(6) ?
C4 C5 H5 . . 111.0 ?
C6 C5 H5 . . 111.0 ?
N1 C5 H5 . . 111.0 ?
C7 C6 C11 . . 120.0 ?
C7 C6 C5 . . 118.5(6) ?
C11 C6 C5 . . 121.4(6) ?
C8 C7 C6 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C8 C9 C10 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C9 C10 C11 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C6 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C6 C11 H11 . . 120.0 ?
C6A C5A C4 . . 117.0(6) ?
C6A C5A N1 . . 110.5(6) ?
C4 C5A N1 . . 103.8(5) ?
C6A C5A H5A . . 108.4 ?
C4 C5A H5A . . 108.4 ?
N1 C5A H5A . . 108.4 ?
C7A C6A C11A . . 119.1(7) ?
C7A C6A C5A . . 121.4(8) ?
C11A C6A C5A . . 119.5(7) ?
C6A C7A C8A . . 121.0(8) ?
C6A C7A H7A . . 119.5 ?
C8A C7A H7A . . 119.5 ?
C9A C8A C7A . . 119.2(9) ?
C9A C8A H8A . . 120.4 ?
C7A C8A H8A . . 120.4 ?
C8A C9A C10A . . 120.2(8) ?
C8A C9A H9A . . 119.9 ?
C10A C9A H9A . . 119.9 ?
C9A C10A C11A . . 120.2(9) ?
C9A C10A H10A . . 119.9 ?
C11A C10A H10A . . 119.9 ?
C10A C11A C6A . . 120.2(8) ?
C10A C11A H11A . . 119.9 ?
C6A C11A H11A . . 119.9 ?
C13 C12 C17 . . 121.5(5) ?
C13 C12 N1 . . 119.7(5) ?
C17 C12 N1 . . 118.7(5) ?
C12 C13 C14 . . 119.0(6) ?
C12 C13 H13 . . 120.5 ?
C14 C13 H13 . . 120.5 ?
C13 C14 C15 . . 120.2(6) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C16 C15 C14 . . 120.1(5) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 120.7(6) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C12 C17 C16 . . 118.4(5) ?
C12 C17 H17 . . 120.8 ?
C16 C17 H17 . . 120.8 ?
C2 N1 C12 . . 120.0(4) ?
C2 N1 C5 . . 114.8(5) ?
C12 N1 C5 . . 118.5(4) ?
C2 N1 C5A . . 117.1(4) ?
C12 N1 C5A . . 118.7(4) ?
C2 N2 C3 . . 118.3(4) ?
C2 S1 C1 . . 102.4(2) ?



