# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_q
_database_code_depnum_ccdc_archive 'CCDC 2371473'
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-09-30 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 N2 O S'
_chemical_formula_sum            'C8 H8 N2 O S'
_chemical_formula_weight         180.22
_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      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                   5.0399(3)
_cell_length_b                   15.0255(11)
_cell_length_c                   11.3318(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.975(2)
_cell_angle_gamma                90
_cell_volume                     856.06(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9260
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8892.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12362
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.255
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             0.9
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1826
_reflns_number_total             2110
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.069
_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)+(0.0466P)²+0.1588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0969
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.45821(7) 0.42184(2) 0.84512(3) 0.05414(14) Uani 1 1 d . . . . .
O1 O 0.5249(3) 0.57699(7) 0.63432(12) 0.0725(4) Uani 1 1 d . . . . .
H1 H 0.502063 0.581087 0.562167 0.109 Uiso 1 1 calc R U . . .
N1 N 0.0764(2) 0.28766(8) 0.77122(10) 0.0513(3) Uani 1 1 d . . . . .
N2 N 0.5205(2) 0.42195(7) 0.61778(12) 0.0533(3) Uani 1 1 d . . . . .
C1 C 0.2069(2) 0.31058(8) 0.67732(10) 0.0416(3) Uani 1 1 d . . . . .
C2 C 0.1659(3) 0.26979(10) 0.56817(12) 0.0540(3) Uani 1 1 d . . . . .
H2 H 0.261844 0.287145 0.504823 0.065 Uiso 1 1 calc R U . . .
C3 C -0.0204(3) 0.20280(10) 0.55566(13) 0.0599(4) Uani 1 1 d . . . . .
H3 H -0.053187 0.174186 0.483341 0.072 Uiso 1 1 calc R U . . .
C4 C -0.1575(3) 0.17878(10) 0.65149(14) 0.0568(3) Uani 1 1 d . . . . .
H4 H -0.284263 0.133747 0.645226 0.068 Uiso 1 1 calc R U . . .
C5 C -0.1032(3) 0.22260(10) 0.75637(14) 0.0580(3) Uani 1 1 d . . . . .
H5 H -0.196680 0.206113 0.820846 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3996(2) 0.38382(8) 0.69867(11) 0.0435(3) Uani 1 1 d . . . . .
C7 C 0.7162(3) 0.49333(11) 0.79707(17) 0.0665(4) Uani 1 1 d . . . . .
H7A H 0.705160 0.551707 0.832936 0.080 Uiso 1 1 calc R U . . .
H7B H 0.890037 0.468306 0.819142 0.080 Uiso 1 1 calc R U . . .
C8 C 0.6724(3) 0.50003(10) 0.66361(16) 0.0635(4) Uani 1 1 d . . . . .
H8 H 0.844253 0.502622 0.628203 0.076 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0492(2) 0.0586(2) 0.0538(2) -0.00523(14) -0.00210(14) -0.00181(14)
O1 0.0990(10) 0.0426(6) 0.0793(8) 0.0003(5) 0.0312(7) 0.0035(5)
N1 0.0586(7) 0.0532(6) 0.0431(6) -0.0002(5) 0.0105(5) -0.0082(5)
N2 0.0567(7) 0.0417(6) 0.0640(7) -0.0001(5) 0.0211(5) -0.0003(5)
C1 0.0431(6) 0.0401(6) 0.0420(6) 0.0032(4) 0.0045(5) 0.0034(5)
C2 0.0645(8) 0.0569(7) 0.0413(6) 0.0007(5) 0.0082(6) -0.0072(6)
C3 0.0731(9) 0.0583(8) 0.0475(7) -0.0061(6) -0.0017(6) -0.0094(7)
C4 0.0549(8) 0.0483(7) 0.0667(9) 0.0013(6) 0.0014(6) -0.0103(6)
C5 0.0625(8) 0.0575(8) 0.0555(8) 0.0039(6) 0.0154(6) -0.0119(7)
C6 0.0414(6) 0.0404(6) 0.0492(6) 0.0005(5) 0.0066(5) 0.0049(5)
C7 0.0443(7) 0.0581(9) 0.0965(12) -0.0103(8) -0.0004(7) -0.0045(6)
C8 0.0545(8) 0.0471(7) 0.0925(12) -0.0069(7) 0.0302(8) -0.0058(6)

_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 C6 1.7606(13) . ?
S1 C7 1.7998(16) . ?
O1 H1 0.8200 . ?
O1 C8 1.4023(19) . ?
N1 C1 1.3341(16) . ?
N1 C5 1.3351(18) . ?
N2 C6 1.2716(16) . ?
N2 C8 1.4755(19) . ?
C1 C2 1.3831(18) . ?
C1 C6 1.4768(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(2) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.517(3) . ?
C8 H8 0.9800 . ?

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
C6 S1 C7 89.19(7) . . ?
C8 O1 H1 109.5 . . ?
C1 N1 C5 117.12(12) . . ?
C6 N2 C8 111.55(13) . . ?
N1 C1 C2 123.21(12) . . ?
N1 C1 C6 114.62(11) . . ?
C2 C1 C6 122.17(11) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.31(13) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.14(13) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.56(13) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 123.66(13) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N2 C6 S1 118.42(10) . . ?
N2 C6 C1 124.07(12) . . ?
C1 C6 S1 117.50(9) . . ?
S1 C7 H7A 110.4 . . ?
S1 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 S1 106.45(10) . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
O1 C8 N2 108.57(13) . . ?
O1 C8 C7 109.20(13) . . ?
O1 C8 H8 109.8 . . ?
N2 C8 C7 109.53(12) . . ?
N2 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?

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 C7 C8 O1 95.59(13) . . . . ?
S1 C7 C8 N2 -23.19(14) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
N1 C1 C6 S1 6.84(15) . . . . ?
N1 C1 C6 N2 -171.61(12) . . . . ?
C1 N1 C5 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C1 C6 S1 -173.39(11) . . . . ?
C2 C1 C6 N2 8.2(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C5 N1 C1 C2 -0.7(2) . . . . ?
C5 N1 C1 C6 179.07(12) . . . . ?
C6 S1 C7 C8 16.85(11) . . . . ?
C6 N2 C8 O1 -99.97(14) . . . . ?
C6 N2 C8 C7 19.20(17) . . . . ?
C6 C1 C2 C3 -179.12(13) . . . . ?
C7 S1 C6 N2 -7.18(12) . . . . ?
C7 S1 C6 C1 174.28(10) . . . . ?
C8 N2 C6 S1 -5.95(16) . . . . ?
C8 N2 C6 C1 172.48(12) . . . . ?

_shelx_res_file                  
;
TITL q_a.res in P2(1)/c
    q.res
    created by SHELXL-2018/3 at 21:58:16 on 15-Jul-2024
REM Old TITL q in P21/c #14
REM SHELXT solution in P2(1)/c: R1 0.128, Rweak 0.004, Alpha 0.039
REM <I/s> 1.319 for 80 systematic absences, Orientation as input
REM Formula found by SHELXT: C8 N3 S
CELL 0.71073 5.0399 15.0255 11.3318 90 93.975 90
ZERR 4 0.0003 0.0011 0.0009 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 32 32 8 4 4

L.S. 4
PLAN  2
SIZE 0.09 0.11 0.13
TEMP 20
CONF
BOND
list 4
fmap 2 53
acta
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\q.hkl">
REM </olex2.extras>

WGHT    0.046600    0.158800
FVAR       1.59998
S1    5    0.458214    0.421841    0.845123    11.00000    0.04920    0.05860 =
         0.05382   -0.00523   -0.00210   -0.00181
O1    4    0.524896    0.576994    0.634315    11.00000    0.09897    0.04261 =
         0.07933    0.00025    0.03123    0.00352
AFIX 147
H1    2    0.502063    0.581087    0.562167    11.00000   -1.50000
AFIX   0
N1    3    0.076450    0.287660    0.771219    11.00000    0.05864    0.05321 =
         0.04306   -0.00017    0.01053   -0.00823
N2    3    0.520488    0.421955    0.617782    11.00000    0.05665    0.04166 =
         0.06398   -0.00010    0.02105   -0.00029
C1    1    0.206863    0.310584    0.677321    11.00000    0.04313    0.04006 =
         0.04198    0.00325    0.00454    0.00337
C2    1    0.165950    0.269789    0.568165    11.00000    0.06453    0.05689 =
         0.04130    0.00069    0.00817   -0.00716
AFIX  43
H2    2    0.261844    0.287145    0.504823    11.00000   -1.20000
AFIX   0
C3    1   -0.020448    0.202797    0.555662    11.00000    0.07315    0.05832 =
         0.04745   -0.00610   -0.00169   -0.00938
AFIX  43
H3    2   -0.053187    0.174186    0.483341    11.00000   -1.20000
AFIX   0
C4    1   -0.157466    0.178776    0.651488    11.00000    0.05494    0.04835 =
         0.06670    0.00134    0.00144   -0.01027
AFIX  43
H4    2   -0.284263    0.133747    0.645226    11.00000   -1.20000
AFIX   0
C5    1   -0.103188    0.222598    0.756372    11.00000    0.06250    0.05754 =
         0.05548    0.00394    0.01545   -0.01187
AFIX  43
H5    2   -0.196680    0.206113    0.820846    11.00000   -1.20000
AFIX   0
C6    1    0.399638    0.383821    0.698675    11.00000    0.04137    0.04041 =
         0.04922    0.00055    0.00658    0.00493
C7    1    0.716223    0.493326    0.797071    11.00000    0.04434    0.05805 =
         0.09649   -0.01026   -0.00036   -0.00451
AFIX  23
H7A   2    0.705160    0.551707    0.832936    11.00000   -1.20000
H7B   2    0.890037    0.468306    0.819142    11.00000   -1.20000
AFIX   0
C8    1    0.672449    0.500025    0.663609    11.00000    0.05445    0.04708 =
         0.09251   -0.00686    0.03018   -0.00577
AFIX  13
H8    2    0.844253    0.502622    0.628203    11.00000   -1.20000
AFIX   0
HKLF 4




REM  q_a.res in P2(1)/c
REM wR2 = 0.0969, GooF = S = 1.069, Restrained GooF = 1.069 for all data
REM R1 = 0.0337 for 1826 Fo > 4sig(Fo) and 0.0400 for all 2110 data
REM 110 parameters refined using 0 restraints

END

WGHT      0.0465      0.1588

REM Highest difference peak  0.221,  deepest hole -0.185,  1-sigma level  0.031
Q1    1   0.4206  0.4016  0.7588  11.00000  0.05    0.22
Q2    1   0.2253  0.2798  0.6318  11.00000  0.05    0.20
;
_shelx_res_checksum              76665
_olex2_submission_special_instructions 'No special instructions were received'
