# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_09am23jcw203
_database_code_depnum_ccdc_archive 'CCDC 2431430'
loop_
_audit_author_name
_audit_author_address
'Antonio Martinez-Martinez'
;University of Huelva
Spain
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-03-14
_audit_creation_method           
;
Olex2 1.5-ac7-014
(compiled 2025.02.27 svn.r6f4c0eaf for Rigaku Oxford Diffraction, GUI svn.r7171)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 N2 O S'
_chemical_formula_sum            'C17 H12 N2 O S'
_chemical_formula_weight         292.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H10 S1 N2 O1'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.64030(10)
_cell_length_b                   7.84000(10)
_cell_length_c                   25.3454(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.1020(10)
_cell_angle_gamma                90
_cell_volume                     2703.49(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20335
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.4670
_cell_measurement_theta_min      3.4800
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    2.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.98a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26066
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.839
_diffrn_reflns_theta_min         3.497
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  45.00   0.50    0.50    --   46.94 -95.00 -42.00   50
  2  ω    -74.00  20.00   0.50    0.50    --  -49.44  95.00  66.00  188
  3  ω    -26.00  31.00   0.50    0.50    --  -49.44  19.00-180.00  114
  4  ω   -120.00 -75.00   0.50    0.50    --  -49.44-125.00  90.00   90
  5  ω    -48.00 -11.00   0.50    0.50    --  -84.69  95.00  66.00   74
  6  ω    -79.00 -53.00   0.50    0.50    --  -84.69  95.00  66.00   52
  7  ω    -32.00  -2.00   0.50    0.50    --  -84.69  30.00-150.00   60
  8  ω    -42.00 -16.00   0.50    0.50    --  -84.69  77.00   0.00   52
  9  ω    -34.00  -3.00   0.50    0.50    --  -84.69  30.00 -90.00   62
 10  ω    -34.00  -3.00   0.50    0.50    --  -84.69  30.00 -30.00   62
 11  ω    -51.00  -6.00   0.50    0.50    --  -84.69  45.00  60.00   90
 12  ω   -123.00 -98.00   0.50    0.50    --  -84.69 -95.00 -42.00   50
 13  ω    -51.00  -6.00   0.50    0.50    --  -84.69  45.00   0.00   90
 14  ω    -91.00 -66.00   0.50    0.50    --  -84.69  77.00   0.00   50
 15  ω     53.00 106.00   0.50    0.50    --  110.85 -95.00 -42.00  106
 16  ω    106.00 143.00   0.50    0.50    --  110.85  95.00  66.00   74
 17  ω     43.00  68.00   0.50    0.50    --  110.85 -61.00-180.00   50
 18  ω     59.00  85.00   0.50    0.50    --  110.85 -77.00   0.00   52
 19  ω     34.00  59.00   0.50    0.50    --  110.85 -61.00 150.00   50
 20  ω    121.00 147.00   0.50    0.50    --  113.75  16.00 -21.15   52
 21  ω     66.00 115.00   0.50    0.50    --  113.75  24.00  11.43   98
 22  ω     45.00  82.00   0.50    0.50    --  113.75  16.00 -21.15   74
 23  ω     45.00  71.00   0.50    0.50    --  113.75 -86.00-179.62   52
 24  ω     51.00 116.00   0.50    0.50    --  113.75 -84.00  40.65  130
 25  ω     41.00 176.00   0.50    0.50    --  113.75   5.00 106.17  270
 26  ω    105.00 130.00   0.50    0.50    --  113.75 -87.00 -69.93   50
 27  ω     47.00  77.00   0.50    0.50    --  113.75 -87.00 -69.93   60
 28  ω    102.00 142.00   0.50    0.50    --  113.75  24.00-176.85   80
 29  ω    110.00 136.00   0.50    0.50    --  113.75 -88.00 111.10   52
 30  ω     81.00 136.00   0.50    0.50    --  113.75 -87.00 153.37  110
 31  ω     68.00  93.00   0.50    0.50    --  113.75  24.00-176.85   50
 32  ω    117.00 143.00   0.50    0.50    --  113.75 -86.00-179.62   52
 33  ω     49.00  74.00   0.50    0.50    --  113.75 -84.00  27.05   50
 34  ω     46.00  92.00   0.50    0.50    --  113.75 -87.00  23.87   92
 35  ω     57.00  96.00   0.50    0.50    --  113.75  13.00 132.01   78
 36  ω    146.00 172.00   0.50    0.50    --  113.75  13.00 132.01   52
 37  ω     45.00  78.00   0.50    0.50    --  113.75 -83.00  89.32   66
 38  ω     49.00  95.00   0.50    0.50    --  113.75 -79.00 115.26   92
 39  ω    149.00 177.00   0.50    0.50    --  113.75  16.00 -21.15   56
 40  ω    106.00 143.00   0.50    0.50    --  113.75 -85.00-107.80   74
 41  ω     50.00  82.00   0.50    0.50    --  113.75 -88.00 111.10   64
 42  ω     72.00  99.00   0.50    0.50    --  110.85 -79.00-154.00   54
 43  ω   -117.00 -74.00   0.50    0.50    --  -49.44-125.00-180.00   86
 44  ω   -114.00 -67.00   0.50    0.50    --  -49.44 -77.00-150.00   94
 45  ω    -53.00 -27.00   0.50    0.50    --  -49.44 -77.00-150.00   52
 46  ω    -32.00  -6.00   0.50    0.50    --  -84.69  30.00 -60.00   52
 47  ω    -32.00  -6.00   0.50    0.50    --  -84.69  30.00  30.00   52
 48  ω    -67.00 -41.00   0.50    0.50    --  -84.69  77.00-120.00   52
 49  ω   -100.00 -62.00   0.50    0.50    --  -84.69  77.00  60.00   76
 50  ω    -34.00  -3.00   0.50    0.50    --  -84.69  30.00-180.00   62
 51  ω    -98.00 -72.00   0.50    0.50    --  -84.69  77.00-120.00   52
 52  ω    -43.00 -17.00   0.50    0.50    --  -84.69  77.00  60.00   52
 53  ω    -64.00 -39.00   0.50    0.50    --  -84.69 125.00  90.00   50
 54  ω    -35.00 -10.00   0.50    0.50    --  -84.69  30.00-120.00   50
 55  ω    123.00 149.00   0.50    0.50    --  110.85  77.00  60.00   52
 56  ω     66.00 111.00   0.50    0.50    --  110.85-125.00 120.00   90
 57  ω     42.00  70.00   0.50    0.50    --  110.85-125.00 -90.00   56
 58  ω     57.00  83.00   0.50    0.50    --  110.85 -95.00 120.00   52
 59  ω     62.00  88.00   0.50    0.50    --  110.85 -95.00-180.00   52
 60  ω     34.00  59.00   0.50    0.50    --  110.85 -61.00 -90.00   50
 61  ω    142.00 168.00   0.50    0.50    --  110.85  61.00   0.00   52
 62  ω     83.00 109.00   0.50    0.50    --  110.85-125.00-180.00   52
 63  ω     86.00 111.00   0.50    0.50    --  110.85-125.00 -90.00   50
 64  ω     76.00 102.00   0.50    0.50    --  110.85 -95.00 150.00   52
 65  ω     54.00  80.00   0.50    0.50    --  110.85-125.00   0.00   52
 66  ω     87.00 113.00   0.50    0.50    --  110.85  61.00   0.00   52
 67  ω     51.00  76.00   0.50    0.50    --  110.85-125.00-180.00   50
 68  ω     42.00  68.00   0.50    0.50    --  110.85 -77.00 150.00   52
 69  ω     47.00  75.00   0.50    0.50    --  113.75 -88.00 153.95   56
 70  ω    126.00 151.00   0.50    0.50    --  113.75 -87.00  69.39   50
 71  ω     50.00  83.00   0.50    0.50    --  113.75 -87.00  69.39   66
 72  ω    106.00 138.00   0.50    0.50    --  113.75 -88.00 153.95   64
 73  ω     56.00 108.00   0.50    0.50    --  113.75-107.00 150.47  104
 74  ω    103.00 128.00   0.50    0.50    --  113.75 -88.00  -2.49   50
 75  ω     49.00  74.00   0.50    0.50    --  113.75 -87.00 -93.43   50
 76  ω     52.00  78.00   0.50    0.50    --  113.75 -88.00  -2.49   52
 77  ω    118.00 143.00   0.50    0.50    --  113.75 -79.00 115.19   50
 78  ω     49.00  84.00   0.50    0.50    --  113.75 -83.00  99.02   70
 79  ω     49.00  74.00   0.50    0.50    --  113.75 -80.00 -17.91   50
 80  ω    105.00 131.00   0.50    0.50    --  113.75  20.00  98.15   52
 81  ω     91.00 117.00   0.50    0.50    --  113.75-132.00  68.62   52
 82  ω     53.00  93.00   0.50    0.50    --  113.75  20.00  98.15   80
 83  ω    109.00 135.00   0.50    0.50    --  113.75  19.00 -36.86   52
 84  ω     49.00  83.00   0.50    0.50    --  113.75  19.00 -36.86   68
 85  ω    116.00 142.00   0.50    0.50    --  113.75 -88.00-137.43   52
 86  ω     46.00  71.00   0.50    0.50    --  113.75 -88.00-137.43   50
 87  ω     46.00  72.00   0.50    0.50    --  113.75 -80.00  51.42   52
 88  ω     83.00 109.00   0.50    0.50    --  113.75-118.00 -55.10   52
 89  ω    119.00 144.00   0.50    0.50    --  113.75 -83.00  89.29   50
 90  ω    118.00 144.00   0.50    0.50    --  113.75  24.00 139.85   52
 91  ω     75.00 100.00   0.50    0.50    --  113.75  24.00 139.85   50
 92  ω    120.00 149.00   0.50    0.50    --  113.75 -84.00  26.95   58
 93  ω     45.00  71.00   0.50    0.50    --  113.75 -82.00-112.71   52
 94  ω     48.00  74.00   0.50    0.50    --  113.75-118.00 -55.10   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0456048000
_diffrn_orient_matrix_UB_12      -0.1795183000
_diffrn_orient_matrix_UB_13      -0.0018595000
_diffrn_orient_matrix_UB_21      -0.0624523000
_diffrn_orient_matrix_UB_22      -0.0373873000
_diffrn_orient_matrix_UB_23      -0.0517790000
_diffrn_orient_matrix_UB_31      0.0826631000
_diffrn_orient_matrix_UB_32      0.0707080000
_diffrn_orient_matrix_UB_33      -0.0320991000
_diffrn_oxdiff_digest_hkl        
;
434cf34aec18010e23cff91aa52a5bc2a6e5a5
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2879
_reflns_number_total             2929
_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 1.171.44.98a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.101a 64-bit (release 13-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.44.98a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-ac7-014 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-014 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+2.2756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0923
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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 0.51089(2) 0.23281(4) 0.49080(2) 0.02855(12) Uani 1 1 d . . . . .
O1 O 0.68731(9) 0.42179(16) 0.39325(4) 0.0440(3) Uani 1 1 d . . . . .
N1 N 0.67528(8) 0.43475(15) 0.50495(4) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.73831(9) 0.54512(15) 0.58696(5) 0.0296(3) Uani 1 1 d . . . . .
C1 C 0.66791(10) 0.44677(17) 0.55867(5) 0.0276(3) Uani 1 1 d . . . . .
C2 C 0.81664(10) 0.6420(2) 0.56489(6) 0.0345(3) Uani 1 1 d . . . . .
H2A H 0.818471 0.615127 0.527207 0.052 Uiso 1 1 calc R U . . .
H2B H 0.879743 0.611760 0.583454 0.052 Uiso 1 1 calc R U . . .
H2C H 0.804471 0.764210 0.569138 0.052 Uiso 1 1 calc R U . . .
C3 C 0.71919(10) 0.54285(18) 0.63929(5) 0.0296(3) Uani 1 1 d . . . . .
C4 C 0.76792(12) 0.6249(2) 0.68261(6) 0.0356(3) Uani 1 1 d . . . . .
H4 H 0.824139 0.693979 0.678610 0.043 Uiso 1 1 calc R U . . .
C5 C 0.73107(13) 0.6016(2) 0.73136(6) 0.0380(3) Uani 1 1 d . . . . .
H5 H 0.762406 0.656551 0.761431 0.046 Uiso 1 1 calc R U . . .
C6 C 0.64864(12) 0.49903(19) 0.73773(6) 0.0369(3) Uani 1 1 d . . . . .
H6 H 0.625722 0.485055 0.771990 0.044 Uiso 1 1 calc R U . . .
C7 C 0.60024(12) 0.41813(19) 0.69527(6) 0.0344(3) Uani 1 1 d . . . . .
H7 H 0.544366 0.348882 0.699947 0.041 Uiso 1 1 calc R U . . .
C8 C 0.63524(10) 0.44010(18) 0.64469(5) 0.0293(3) Uani 1 1 d . . . . .
C9 C 0.60343(10) 0.38110(18) 0.59356(5) 0.0297(3) Uani 1 1 d . . . . .
H9 H 0.548323 0.309929 0.584719 0.036 Uiso 1 1 calc R U . . .
C10 C 0.61422(10) 0.35066(17) 0.47427(5) 0.0270(3) Uani 1 1 d . . . . .
C11 C 0.62460(10) 0.34426(18) 0.41483(5) 0.0295(3) Uani 1 1 d . . . . .
C12 C 0.54708(10) 0.23646(17) 0.38925(5) 0.0267(3) Uani 1 1 d . . . . .
C13 C 0.53375(11) 0.19673(19) 0.33562(5) 0.0311(3) Uani 1 1 d . . . . .
H13 H 0.578712 0.236744 0.311488 0.037 Uiso 1 1 calc R U . . .
C14 C 0.45386(11) 0.0980(2) 0.31817(5) 0.0326(3) Uani 1 1 d . . . . .
H14 H 0.443946 0.069615 0.281736 0.039 Uiso 1 1 calc R U . . .
C15 C 0.38786(11) 0.03973(19) 0.35357(5) 0.0316(3) Uani 1 1 d . . . . .
H15 H 0.332871 -0.026534 0.340797 0.038 Uiso 1 1 calc R U . . .
C16 C 0.40096(10) 0.07681(18) 0.40728(5) 0.0292(3) Uani 1 1 d . . . . .
H16 H 0.356194 0.036098 0.431416 0.035 Uiso 1 1 calc R U . . .
C17 C 0.48126(10) 0.17486(17) 0.42436(5) 0.0259(3) Uani 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 C10 1.7608(13) . ?
S1 C17 1.7630(13) . ?
O1 C11 1.2112(17) . ?
N1 C1 1.3758(17) . ?
N1 C10 1.2807(18) . ?
N2 C1 1.3900(17) . ?
N2 C2 1.4547(17) . ?
N2 C3 1.3702(18) . ?
C1 C9 1.3898(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.399(2) . ?
C3 C8 1.415(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.4102(19) . ?
C8 C9 1.4148(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.5241(18) . ?
C11 C12 1.4679(19) . ?
C12 C13 1.3936(19) . ?
C12 C17 1.3947(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3909(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3822(19) . ?

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
C10 S1 C17 92.33(6) . . ?
C10 N1 C1 123.08(12) . . ?
C1 N2 C2 126.19(12) . . ?
C3 N2 C1 108.65(11) . . ?
C3 N2 C2 125.09(12) . . ?
N1 C1 N2 116.86(12) . . ?
N1 C1 C9 134.32(13) . . ?
C9 C1 N2 108.83(12) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C4 129.88(14) . . ?
N2 C3 C8 108.21(12) . . ?
C4 C3 C8 121.90(14) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.32(15) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.76(14) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.23(14) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.67(14) . . ?
C8 C7 H7 120.7 . . ?
C3 C8 C9 107.15(12) . . ?
C7 C8 C3 119.11(13) . . ?
C7 C8 C9 133.73(14) . . ?
C1 C9 C8 107.16(12) . . ?
C1 C9 H9 126.4 . . ?
C8 C9 H9 126.4 . . ?
N1 C10 S1 128.50(11) . . ?
N1 C10 C11 120.98(12) . . ?
C11 C10 S1 110.52(9) . . ?
O1 C11 C10 123.25(12) . . ?
O1 C11 C12 126.82(13) . . ?
C12 C11 C10 109.91(11) . . ?
C13 C12 C11 126.80(12) . . ?
C13 C12 C17 119.99(13) . . ?
C17 C12 C11 113.19(12) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.81(13) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.54(13) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.22(13) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 121.1 . . ?
C17 C16 C15 117.79(13) . . ?
C17 C16 H16 121.1 . . ?
C12 C17 S1 113.96(10) . . ?
C16 C17 S1 124.39(10) . . ?
C16 C17 C12 121.64(12) . . ?

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 C10 C11 O1 176.49(13) . . . . ?
S1 C10 C11 C12 -1.97(14) . . . . ?
O1 C11 C12 C13 3.2(3) . . . . ?
O1 C11 C12 C17 -175.29(15) . . . . ?
N1 C1 C9 C8 179.94(15) . . . . ?
N1 C10 C11 O1 -2.9(2) . . . . ?
N1 C10 C11 C12 178.60(13) . . . . ?
N2 C1 C9 C8 -0.22(16) . . . . ?
N2 C3 C4 C5 178.97(15) . . . . ?
N2 C3 C8 C7 -179.74(13) . . . . ?
N2 C3 C8 C9 -0.51(16) . . . . ?
C1 N1 C10 S1 -0.5(2) . . . . ?
C1 N1 C10 C11 178.80(13) . . . . ?
C1 N2 C3 C4 -178.53(15) . . . . ?
C1 N2 C3 C8 0.38(16) . . . . ?
C2 N2 C1 N1 2.6(2) . . . . ?
C2 N2 C1 C9 -177.25(13) . . . . ?
C2 N2 C3 C4 -1.3(2) . . . . ?
C2 N2 C3 C8 177.57(13) . . . . ?
C3 N2 C1 N1 179.77(12) . . . . ?
C3 N2 C1 C9 -0.10(16) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C8 C9 C1 0.45(16) . . . . ?
C4 C3 C8 C7 -0.7(2) . . . . ?
C4 C3 C8 C9 178.50(13) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C3 0.6(2) . . . . ?
C6 C7 C8 C9 -178.38(15) . . . . ?
C7 C8 C9 C1 179.51(16) . . . . ?
C8 C3 C4 C5 0.2(2) . . . . ?
C10 S1 C17 C12 1.47(11) . . . . ?
C10 S1 C17 C16 -178.81(13) . . . . ?
C10 N1 C1 N2 -178.78(13) . . . . ?
C10 N1 C1 C9 1.1(3) . . . . ?
C10 C11 C12 C13 -178.43(14) . . . . ?
C10 C11 C12 C17 3.10(17) . . . . ?
C11 C12 C13 C14 -177.48(14) . . . . ?
C11 C12 C17 S1 -2.94(16) . . . . ?
C11 C12 C17 C16 177.33(13) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C12 C17 S1 178.47(11) . . . . ?
C13 C12 C17 C16 -1.3(2) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C16 C17 S1 -179.20(11) . . . . ?
C15 C16 C17 C12 0.5(2) . . . . ?
C17 S1 C10 N1 179.73(14) . . . . ?
C17 S1 C10 C11 0.35(11) . . . . ?
C17 C12 C13 C14 0.9(2) . . . . ?

_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 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.586
####################################################################### 
# 
# 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_maf02
_database_code_depnum_ccdc_archive 'CCDC 2431431'
loop_
_audit_author_name
_audit_author_address
'Antonio Martinez-Martinez'
;University of Huelva
Spain
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-03-14
_audit_creation_method           
;
Olex2 1.5-ac7-014
(compiled 2025.02.27 svn.r6f4c0eaf for Rigaku Oxford Diffraction, GUI svn.r7171)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 N3 O S'
_chemical_formula_sum            'C15 H9 N3 O S'
_chemical_formula_weight         279.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H9 N3 O1 S1 '
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.7360(4)
_cell_length_b                   4.87140(10)
_cell_length_c                   26.2576(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.070(2)
_cell_angle_gamma                90
_cell_volume                     2477.49(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18483
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      33.7260
_cell_measurement_theta_min      2.3750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.98a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0300
1 0 0 0.0246
0 0 1 0.0126
0 0 -1 0.0378
-1 0 -2 0.0405
0 1 0 0.0691
0 -2 1 0.1378
1 0 -2 0.0310
2 0 -1 0.0232
-2 0 1 0.0311
2 -1 -2 0.1229
-17 -1 33 0.0289
12 -5 -23 0.1044

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9999 0.0000 -0.0000 -0.0090 -0.0329 0.0133
0.9999 -0.0000 0.0000 0.0090 0.0329 -0.0133
-0.0000 -0.0001 0.9998 0.0212 0.0066 0.0162
0.0000 0.0001 -0.9998 -0.0212 -0.0066 -0.0162
-0.9999 0.0002 -1.9996 -0.0515 -0.0461 -0.0191
0.0013 1.0002 -0.0003 -0.0916 0.0631 0.0941
-0.0025 -2.0004 1.0004 0.2043 -0.1196 -0.1719
0.9999 0.0001 -1.9996 -0.0334 0.0197 -0.0457
1.9998 0.0000 -0.9998 -0.0032 0.0592 -0.0428
-1.9998 -0.0000 0.9998 0.0032 -0.0592 0.0428
1.9986 -1.0001 -1.9992 0.0671 -0.0105 -0.1531
-16.7335 -0.8127 32.9855 0.6236 -0.3841 0.6809
12.3335 -4.9256 -22.6907 0.0806 -0.0545 -0.9953

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            33247
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.846
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  80.00   0.50   40.00    --    8.84  67.00  32.00  182
  2  ω    -62.00  29.00   0.50   40.00    --    8.84 -67.00-101.00  182
  3  ω    -68.00  23.00   0.50   40.00    --    8.84 -38.00 -90.00  182
  4  ω    -58.00  33.00   0.50   40.00    --    8.84 -77.00  30.00  182
  5  ω    -58.00  33.00   0.50   40.00    --    8.84 -77.00  30.00  182
  6  ω    -23.00  28.00   0.50   40.00    --   -9.15 -99.00 -90.00  102
  7  ω    -23.00  28.00   0.50   40.00    --   -9.15 -99.00  30.00  102
  8  ω    -23.00  28.00   0.50   40.00    --   -9.15 -99.00 120.00  102
  9  ω    -23.00  22.00   0.50   40.00    --    8.84 -99.00-180.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0090252000
_diffrn_orient_matrix_UB_12      -0.0915420000
_diffrn_orient_matrix_UB_13      0.0212272000
_diffrn_orient_matrix_UB_21      0.0329145000
_diffrn_orient_matrix_UB_22      0.0630551000
_diffrn_orient_matrix_UB_23      0.0066058000
_diffrn_orient_matrix_UB_31      -0.0132784000
_diffrn_orient_matrix_UB_32      0.0940707000
_diffrn_orient_matrix_UB_33      0.0162239000
_diffrn_oxdiff_digest_hkl        
;
439bffcd13249911e68b7e689dad21b3a4d399
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3768
_reflns_number_total             4492
_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 1.171.44.98a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.111a 64-bit (release 27-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.44.98a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-ac7-014 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-014 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+1.3079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C6(H6), C11(H11), C5(H5), C4(H4), C12(H12), C13(H13)
;
_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 0.47702(2) 0.85282(6) 0.67117(2) 0.02714(8) Uani 1 1 d . . . . .
O1 O 0.38303(5) 1.3256(2) 0.56205(4) 0.0457(3) Uani 1 1 d . . . . .
N2 N 0.57071(5) 0.6640(2) 0.53620(4) 0.02580(18) Uani 1 1 d . . . . .
N3 N 0.55735(5) 0.5765(2) 0.61774(4) 0.02744(19) Uani 1 1 d . . . . .
N1 N 0.48661(5) 0.9263(2) 0.56884(3) 0.02598(18) Uani 1 1 d . . . . .
C10 C 0.37924(5) 1.2395(2) 0.65135(4) 0.0263(2) Uani 1 1 d . . . . .
C9 C 0.40331(6) 1.2047(2) 0.60234(4) 0.0284(2) Uani 1 1 d . . . . .
C1 C 0.53689(5) 0.7255(2) 0.57542(4) 0.02433(19) Uani 1 1 d . . . . .
C7 C 0.60816(5) 0.4094(2) 0.60562(4) 0.0259(2) Uani 1 1 d . . . . .
C15 C 0.41357(5) 1.0663(2) 0.68999(4) 0.0264(2) Uani 1 1 d . . . . .
C2 C 0.61770(5) 0.4614(2) 0.55458(4) 0.0253(2) Uani 1 1 d . . . . .
C8 C 0.45922(5) 0.9871(2) 0.60820(4) 0.02434(19) Uani 1 1 d . . . . .
C3 C 0.66667(6) 0.3183(2) 0.53291(5) 0.0312(2) Uani 1 1 d . . . . .
H3 H 0.673254 0.354270 0.498631 0.037 Uiso 1 1 calc R U . . .
C14 C 0.39748(6) 1.0671(3) 0.73925(4) 0.0329(2) Uani 1 1 d . . . . .
H14 H 0.420290 0.947294 0.765599 0.039 Uiso 1 1 calc R U . . .
C6 C 0.64768(6) 0.2091(3) 0.63601(5) 0.0320(2) Uani 1 1 d . . . . .
H6 H 0.641576 0.172153 0.670363 0.038 Uiso 1 1 calc R U . . .
C11 C 0.32898(6) 1.4219(3) 0.66112(5) 0.0324(2) Uani 1 1 d . . . . .
H11 H 0.305984 1.541094 0.634724 0.039 Uiso 1 1 calc R U . . .
C5 C 0.69561(6) 0.0674(3) 0.61465(5) 0.0337(2) Uani 1 1 d . . . . .
H5 H 0.722889 -0.069875 0.634580 0.040 Uiso 1 1 calc R U . . .
C4 C 0.70506(6) 0.1216(2) 0.56384(5) 0.0332(2) Uani 1 1 d . . . . .
H4 H 0.738797 0.020295 0.550370 0.040 Uiso 1 1 calc R U . . .
C12 C 0.31329(7) 1.4253(3) 0.71054(5) 0.0370(3) Uani 1 1 d . . . . .
H12 H 0.279390 1.548811 0.718231 0.044 Uiso 1 1 calc R U . . .
C13 C 0.34707(7) 1.2484(3) 0.74879(5) 0.0372(3) Uani 1 1 d . . . . .
H13 H 0.335340 1.251809 0.782225 0.045 Uiso 1 1 calc R U . . .
H2 H 0.5650(8) 0.731(3) 0.5068(6) 0.037(4) 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 C15 1.7696(11) . ?
S1 C8 1.7500(10) . ?
O1 C9 1.2097(14) . ?
N2 C1 1.3639(13) . ?
N2 C2 1.3765(14) . ?
N2 H2 0.826(17) . ?
N3 C1 1.3238(13) . ?
N3 C7 1.3756(14) . ?
N1 C1 1.3805(13) . ?
N1 C8 1.2893(13) . ?
C10 C9 1.4646(15) . ?
C10 C15 1.3917(16) . ?
C10 C11 1.3921(16) . ?
C9 C8 1.5166(15) . ?
C7 C2 1.4117(14) . ?
C7 C6 1.3992(15) . ?
C15 C14 1.3897(14) . ?
C2 C3 1.3981(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3839(16) . ?
C14 H14 0.9500 . ?
C14 C13 1.3887(18) . ?
C6 H6 0.9500 . ?
C6 C5 1.3746(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3906(17) . ?
C5 H5 0.9500 . ?
C5 C4 1.4072(18) . ?
C4 H4 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.392(2) . ?
C13 H13 0.9500 . ?

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 C15 91.13(5) . . ?
C1 N2 C2 106.70(9) . . ?
C1 N2 H2 128.2(11) . . ?
C2 N2 H2 125.1(11) . . ?
C1 N3 C7 104.41(9) . . ?
C8 N1 C1 117.67(9) . . ?
C15 C10 C9 112.09(10) . . ?
C15 C10 C11 121.14(10) . . ?
C11 C10 C9 126.77(11) . . ?
O1 C9 C10 127.12(11) . . ?
O1 C9 C8 122.76(10) . . ?
C10 C9 C8 110.12(9) . . ?
N2 C1 N1 120.37(9) . . ?
N3 C1 N2 113.49(9) . . ?
N3 C1 N1 126.14(9) . . ?
N3 C7 C2 110.45(9) . . ?
N3 C7 C6 129.21(10) . . ?
C6 C7 C2 120.34(10) . . ?
C10 C15 S1 115.10(8) . . ?
C14 C15 S1 124.20(10) . . ?
C14 C15 C10 120.70(11) . . ?
N2 C2 C7 104.94(9) . . ?
N2 C2 C3 133.36(10) . . ?
C3 C2 C7 121.70(10) . . ?
N1 C8 S1 129.23(8) . . ?
N1 C8 C9 119.21(9) . . ?
C9 C8 S1 111.56(7) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 C2 116.72(11) . . ?
C4 C3 H3 121.6 . . ?
C15 C14 H14 121.0 . . ?
C13 C14 C15 118.00(12) . . ?
C13 C14 H14 121.0 . . ?
C7 C6 H6 121.0 . . ?
C5 C6 C7 118.00(11) . . ?
C5 C6 H6 121.0 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.27(12) . . ?
C12 C11 H11 120.9 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.28(11) . . ?
C4 C5 H5 119.4 . . ?
C3 C4 C5 121.95(11) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.29(12) . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 121.58(11) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 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 C15 C14 C13 179.16(9) . . . . ?
O1 C9 C8 S1 179.74(11) . . . . ?
O1 C9 C8 N1 -0.08(18) . . . . ?
N2 C2 C3 C4 -179.28(12) . . . . ?
N3 C7 C2 N2 -0.37(12) . . . . ?
N3 C7 C2 C3 179.85(10) . . . . ?
N3 C7 C6 C5 179.75(12) . . . . ?
C10 C9 C8 S1 -0.60(12) . . . . ?
C10 C9 C8 N1 179.57(10) . . . . ?
C10 C15 C14 C13 -0.96(17) . . . . ?
C10 C11 C12 C13 -0.40(18) . . . . ?
C9 C10 C15 S1 0.47(13) . . . . ?
C9 C10 C15 C14 -179.42(10) . . . . ?
C9 C10 C11 C12 -179.76(11) . . . . ?
C1 N2 C2 C7 0.73(12) . . . . ?
C1 N2 C2 C3 -179.53(12) . . . . ?
C1 N3 C7 C2 -0.15(12) . . . . ?
C1 N3 C7 C6 -179.76(12) . . . . ?
C1 N1 C8 S1 0.79(16) . . . . ?
C1 N1 C8 C9 -179.42(10) . . . . ?
C7 N3 C1 N2 0.65(13) . . . . ?
C7 N3 C1 N1 -179.44(11) . . . . ?
C7 C2 C3 C4 0.42(17) . . . . ?
C7 C6 C5 C4 0.19(19) . . . . ?
C15 S1 C8 N1 -179.47(11) . . . . ?
C15 S1 C8 C9 0.72(8) . . . . ?
C15 C10 C9 O1 179.72(13) . . . . ?
C15 C10 C9 C8 0.09(13) . . . . ?
C15 C10 C11 C12 -0.62(17) . . . . ?
C15 C14 C13 C12 -0.06(18) . . . . ?
C2 N2 C1 N3 -0.91(13) . . . . ?
C2 N2 C1 N1 179.18(10) . . . . ?
C2 C7 C6 C5 0.18(18) . . . . ?
C2 C3 C4 C5 -0.04(19) . . . . ?
C8 S1 C15 C10 -0.71(9) . . . . ?
C8 S1 C15 C14 179.17(10) . . . . ?
C8 N1 C1 N2 -176.02(10) . . . . ?
C8 N1 C1 N3 4.08(17) . . . . ?
C6 C7 C2 N2 179.27(11) . . . . ?
C6 C7 C2 C3 -0.50(17) . . . . ?
C6 C5 C4 C3 -0.3(2) . . . . ?
C11 C10 C9 O1 -1.1(2) . . . . ?
C11 C10 C9 C8 179.30(11) . . . . ?
C11 C10 C15 S1 -178.79(9) . . . . ?
C11 C10 C15 C14 1.32(17) . . . . ?
C11 C12 C13 C14 0.75(19) . . . . ?

_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 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.812
####################################################################### 
# 
# 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_080am25jialie_mpsneoviired
_database_code_depnum_ccdc_archive 'CCDC 2431432'
loop_
_audit_author_name
_audit_author_address
'Antonio Martinez-Martinez'
;University of Huelva
Spain
;
_audit_update_record             
;
2025-03-14 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-02-07
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N3 O S'
_chemical_formula_sum            'C16 H11 N3 O S'
_chemical_formula_weight         293.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNSO
_chemical_oxdiff_usercomment     'orange plate'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.62660(10)
_cell_length_b                   7.92250(10)
_cell_length_c                   24.4377(3)
_cell_angle_alpha                81.1440(10)
_cell_angle_beta                 82.1160(10)
_cell_angle_gamma                64.1260(10)
_cell_volume                     1308.64(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35456
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.5610
_cell_measurement_theta_min      3.6680
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 2 0.0539
0 1 2 0.0740
0 -1 -2 0.0493
-1 -1 2 0.0478
-1 -2 -1 0.0618
-1 0 2 0.0565
-1 -1 0 0.0602
1 2 2 0.0720
1 1 1 0.0711
0 1 -2 0.0425
0 -1 1 0.0532
0 0 1 0.0293
0 0 -1 0.0167
2 1 -1 0.0543
-2 -1 1 0.0572
-2 1 1 0.0599
1 0 0 0.0652
2 1 1 0.0564

_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.046
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -2.0000 2.0000 0.3250 -0.0369 -0.2868
-0.0000 1.0000 2.0000 0.0433 -0.0292 0.2345
0.0000 -1.0000 -2.0000 -0.0433 0.0292 -0.2345
-1.0000 -1.0000 2.0000 0.2528 -0.1033 -0.0929
-1.0000 -2.0000 -1.0000 0.1517 -0.0927 -0.3477
-1.0000 -0.0000 2.0000 0.1806 -0.1698 0.1010
-1.0000 -1.0000 0.0000 0.1372 -0.1406 -0.1335
1.0000 2.0000 2.0000 -0.0939 0.1114 0.3681
1.0000 1.0000 1.0000 -0.0795 0.1592 0.1538
-0.0000 1.0000 -2.0000 -0.1877 -0.1036 0.1533
0.0000 -1.0000 1.0000 0.1300 0.0850 -0.1736
-0.0000 -0.0000 1.0000 0.0578 0.0186 0.0203
0.0000 0.0000 -1.0000 -0.0578 -0.0186 -0.0203
2.0000 1.0000 -1.0000 -0.2601 0.3289 0.0528
-2.0000 -1.0000 1.0000 0.2601 -0.3289 -0.0528
-2.0000 1.0000 1.0000 0.1157 -0.4617 0.3351
1.0000 0.0000 0.0000 -0.0651 0.2070 -0.0604
2.0000 1.0000 1.0000 -0.1445 0.3661 0.0934

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            55004
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.130
_diffrn_reflns_theta_min         3.672
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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  89.00   0.50    0.50    --   52.16 -99.00 145.00  180
  2  ω    -80.00  13.00   0.50    0.50    --  -54.91  99.00-109.00  186
  3  ω   -145.00 -86.00   0.50    0.50    --  -77.84 -99.00 145.00  118
  4  ω    -80.00 -10.00   0.50    0.50    --  -77.84  99.00-109.00  140
  5  ω     36.00 106.00   0.50    2.00    --  102.95 -99.00 145.00  140
  6  ω    107.00 170.00   0.50    2.00    --  102.95  99.00-109.00  126
  7  ω     -4.00  22.00   0.50    0.50    --   34.00 100.00  46.05   52
  8  ω     -1.00  89.00   0.50    0.50    --   52.16 -99.00  30.00  180
  9  ω     -1.00  89.00   0.50    0.50    --   52.16 -99.00  30.00  180
 10  ω    -80.00  13.00   0.50    0.50    --  -54.91  99.00-109.00  186
 11  ω   -122.00 -30.00   0.50    0.50    --  -54.91 -77.00 -30.00  184
 12  ω     38.00 129.00   0.50    0.50    --   62.00  77.00  65.98  182
 13  ω    -40.00   0.00   0.50    0.50    --  -77.84  30.00 -90.00   80
 14  ω    -99.00 -11.00   0.50    0.50    --  -77.84  77.00-180.00  176
 15  ω    -35.00  -2.00   0.50    0.50    --  -77.84  15.00  90.00   66
 16  ω    -35.00  -2.00   0.50    0.50    --  -77.84  15.00-120.00   66
 17  ω    -99.00 -11.00   0.50    0.50    --  -77.84  77.00-180.00  176
 18  ω   -153.00 -62.00   0.50    2.00    --  -86.25 -77.00   0.11  182
 19  ω     36.00 105.00   0.50    2.00    --  102.95 -95.00  30.00  138
 20  ω     34.00 111.00   0.50    2.00    --  102.95-125.00 -90.00  154
 21  ω     34.00 111.00   0.50    2.00    --  102.95-125.00 120.00  154
 22  ω     34.00 111.00   0.50    2.00    --  102.95-125.00 -90.00  154
 23  ω     30.00  69.00   0.50    2.00    --  102.95 -61.00 -90.00   78
 24  ω     30.00  69.00   0.50    2.00    --  102.95 -61.00  30.00   78
 25  ω     36.00 105.00   0.50    2.00    --  102.95 -95.00 -30.00  138
 26  ω     36.00  97.00   0.50    2.00    --  102.95 -77.00 150.00  122
 27  ω     36.00 105.00   0.50    2.00    --  102.95 -95.00   0.00  138
 28  ω     95.00 173.00   0.50    2.00    --  102.95 125.00-180.00  156
 29  ω     30.00  69.00   0.50    2.00    --  102.95 -61.00-180.00   78
 30  ω     30.00  69.00   0.50    2.00    --  102.95 -61.00   0.00   78
 31  ω     79.00 170.00   0.50    2.00    --  102.95  77.00 -90.00  182
 32  ω     89.00 178.00   0.50    2.00    --  102.95  45.00   0.00  178
 33  ω     34.00 111.00   0.50    2.00    --  102.95-125.00 150.00  154
 34  ω     30.00  69.00   0.50    2.00    --  102.95 -61.00 120.00   78
 35  ω     36.00 105.00   0.50    2.00    --  102.95 -95.00 -90.00  138
 36  ω     30.00  69.00   0.50    2.00    --  102.95 -61.00-150.00   78
 37  ω     79.00 170.00   0.50    2.00    --  102.95  77.00 -90.00  182
 38  ω     50.00 178.00   0.50    2.00    --  102.95  15.00 -30.00  256
 39  ω     30.00  69.00   0.50    2.00    --  102.95 -61.00  60.00   78
 40  ω     50.00 178.00   0.50    2.00    --  102.95  15.00 -30.00  256
 41  ω     34.00 111.00   0.50    2.00    --  102.95-125.00 120.00  154
 42  ω     36.00  97.00   0.50    2.00    --  102.95 -77.00-180.00  122
 43  ω     86.00 178.00   0.50    2.00    --  102.95  30.00  60.00  184
 44  ω     86.00 178.00   0.50    2.00    --  102.95  30.00  60.00  184
 45  ω     36.00 105.00   0.50    2.00    --  102.95 -95.00 -60.00  138
 46  ω     36.00 105.00   0.50    2.00    --  102.95 -95.00  90.00  138
 47  ω     89.00 178.00   0.50    2.00    --  102.95  45.00-180.00  178
 48  ω    -52.00 -26.00   0.50    0.50    --   18.00 151.00-126.75   52
 49  ω      8.00  34.00   0.50    0.50    --   42.00  93.00 173.63   52
 50  ω     14.00  43.00   0.50    0.50    --   46.00  90.00-100.36   58
 51  ω     14.00  43.00   0.50    0.50    --   46.00  90.00 125.49   58
 52  ω     40.00 131.00   0.50    0.50    --   62.00  74.00 -68.86  182
 53  ω     38.00 130.00   0.50    0.50    --   62.00  76.00-153.41  184
 54  ω     43.00 134.00   0.50    0.50    --   66.00  75.00 128.74  182
 55  ω   -141.00 -50.00   0.50    0.50    --  -70.00 -67.00-133.82  182
 56  ω   -145.00 -53.00   0.50    0.50    --  -77.84 -77.00  60.00  184
 57  ω   -145.00 -53.00   0.50    0.50    --  -77.84 -77.00 120.00  184
 58  ω   -145.00 -53.00   0.50    0.50    --  -77.84 -77.00 -60.00  184
 59  ω   -145.00 -53.00   0.50    0.50    --  -77.84 -77.00-150.00  184
 60  ω   -153.00 -62.00   0.50    2.00    --  -86.25 -77.00 177.17  182
 61  ω   -154.00 -62.00   0.50    2.00    --  -86.25 -76.00  42.24  184
 62  ω   -153.00 -62.00   0.50    2.00    --  -86.25 -77.00 -76.69  182
 63  ω     89.00 178.00   0.50    2.00    --  102.95  45.00 150.00  178
 64  ω     79.00 170.00   0.50    2.00    --  102.95  77.00 -60.00  182
 65  ω     85.00 118.00   0.50    2.00    --  102.95  61.00-120.00   66
 66  ω     79.00 170.00   0.50    2.00    --  102.95  77.00-150.00  182
 67  ω     79.00 170.00   0.50    2.00    --  102.95  77.00-180.00  182
 68  ω     79.00 170.00   0.50    2.00    --  102.95  77.00  30.00  182
 69  ω     79.00 170.00   0.50    2.00    --  102.95  77.00  60.00  182
 70  ω     79.00 170.00   0.50    2.00    --  102.95  77.00  90.00  182
 71  ω     89.00 178.00   0.50    2.00    --  102.95  45.00 120.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650511000
_diffrn_orient_matrix_UB_12      -0.0721955000
_diffrn_orient_matrix_UB_13      0.0577713000
_diffrn_orient_matrix_UB_21      0.2069628000
_diffrn_orient_matrix_UB_22      -0.0664107000
_diffrn_orient_matrix_UB_23      0.0186047000
_diffrn_orient_matrix_UB_31      -0.0604270000
_diffrn_orient_matrix_UB_32      0.1939359000
_diffrn_orient_matrix_UB_33      0.0203050000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5203
_reflns_number_total             5503
_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 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.5638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0929
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23), C28(H28), C29(H29), C30(H30), C31(H31)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C18(H18A,H18B,H18C)
;
_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 0.22541(5) 0.84009(5) 0.93679(2) 0.02770(10) Uani 1 1 d . . . . .
O1 O -0.24520(15) 1.09725(16) 0.85828(5) 0.0377(3) Uani 1 1 d . . . . .
N1 N -0.14370(17) 0.85391(16) 0.95750(5) 0.0272(2) Uani 1 1 d . . . . .
N2 N -0.23081(17) 0.69724(16) 1.03918(5) 0.0267(2) Uani 1 1 d . . . . .
N3 N 0.07541(17) 0.67903(17) 1.03031(5) 0.0290(3) Uani 1 1 d . . . . .
C1 C -0.0931(2) 0.74416(19) 1.00731(6) 0.0264(3) Uani 1 1 d . . . . .
C2 C -0.4239(2) 0.7352(2) 1.02433(6) 0.0328(3) Uani 1 1 d . . . . .
H2A H -0.428350 0.616158 1.020102 0.049 Uiso 1 1 calc R U . . .
H2B H -0.451162 0.817221 0.989225 0.049 Uiso 1 1 calc R U . . .
H2C H -0.522376 0.797920 1.053653 0.049 Uiso 1 1 calc R U . . .
C3 C -0.1447(2) 0.59234(19) 1.08629(6) 0.0268(3) Uani 1 1 d . . . . .
C4 C -0.2158(2) 0.5089(2) 1.13278(6) 0.0309(3) Uani 1 1 d . . . . .
H4 H -0.345300 0.518404 1.136290 0.037 Uiso 1 1 calc R U . . .
C5 C -0.0885(2) 0.4115(2) 1.17356(6) 0.0339(3) Uani 1 1 d . . . . .
H5 H -0.130913 0.351717 1.205911 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1027(2) 0.3990(2) 1.16825(6) 0.0346(3) Uani 1 1 d . . . . .
H6 H 0.186193 0.330919 1.197177 0.042 Uiso 1 1 calc R U . . .
C7 C 0.1723(2) 0.4826(2) 1.12220(6) 0.0327(3) Uani 1 1 d . . . . .
H7 H 0.301670 0.473322 1.119103 0.039 Uiso 1 1 calc R U . . .
C8 C 0.0462(2) 0.58183(19) 1.08015(6) 0.0275(3) Uani 1 1 d . . . . .
C9 C -0.0193(2) 0.90055(19) 0.92653(6) 0.0269(3) Uani 1 1 d . . . . .
C10 C -0.0786(2) 1.0253(2) 0.87201(6) 0.0291(3) Uani 1 1 d . . . . .
C11 C 0.0908(2) 1.0460(2) 0.84133(6) 0.0282(3) Uani 1 1 d . . . . .
C12 C 0.0946(2) 1.1443(2) 0.78927(6) 0.0314(3) Uani 1 1 d . . . . .
H12 H -0.019284 1.203988 0.769327 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2682(2) 1.1536(2) 0.76695(7) 0.0337(3) Uani 1 1 d . . . . .
H13 H 0.274868 1.217456 0.731033 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4323(2) 1.0691(2) 0.79741(7) 0.0336(3) Uani 1 1 d . . . . .
H14 H 0.549757 1.077561 0.781909 0.040 Uiso 1 1 calc R U . . .
C15 C 0.4291(2) 0.9726(2) 0.84984(7) 0.0308(3) Uani 1 1 d . . . . .
H15 H 0.541527 0.917183 0.870425 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2566(2) 0.95977(19) 0.87115(6) 0.0273(3) Uani 1 1 d . . . . .
S2 S -0.21669(5) 1.26648(5) 0.48900(2) 0.02898(10) Uani 1 1 d . . . . .
O2 O -0.1814(2) 1.66840(16) 0.38208(5) 0.0422(3) Uani 1 1 d . . . . .
N4 N -0.26643(18) 1.62645(17) 0.49820(5) 0.0297(3) Uani 1 1 d . . . . .
N5 N -0.35850(18) 1.74346(17) 0.58651(5) 0.0286(3) Uani 1 1 d . . . . .
N6 N -0.31981(19) 1.44585(17) 0.58300(5) 0.0312(3) Uani 1 1 d . . . . .
C17 C -0.3130(2) 1.5996(2) 0.55444(6) 0.0285(3) Uani 1 1 d . . . . .
C18 C -0.3688(2) 1.9316(2) 0.56836(7) 0.0343(3) Uani 1 1 d . . . . .
H18A H -0.503596 2.025924 0.574716 0.051 Uiso 1 1 calc R U . . .
H18B H -0.327033 1.940358 0.528678 0.051 Uiso 1 1 calc R U . . .
H18C H -0.282767 1.955050 0.589488 0.051 Uiso 1 1 calc R U . . .
C19 C -0.3970(2) 1.6764(2) 0.63991(6) 0.0281(3) Uani 1 1 d . . . . .
C20 C -0.4522(2) 1.7595(2) 0.68926(6) 0.0328(3) Uani 1 1 d . . . . .
H20 H -0.470883 1.885625 0.690460 0.039 Uiso 1 1 calc R U . . .
C21 C -0.4785(2) 1.6499(2) 0.73654(6) 0.0345(3) Uani 1 1 d . . . . .
H21 H -0.515703 1.701530 0.771147 0.041 Uiso 1 1 calc R U . . .
C22 C -0.4515(2) 1.4634(2) 0.73459(6) 0.0344(3) Uani 1 1 d . . . . .
H22 H -0.469237 1.391627 0.768001 0.041 Uiso 1 1 calc R U . . .
C23 C -0.3998(2) 1.3823(2) 0.68539(6) 0.0327(3) Uani 1 1 d . . . . .
H23 H -0.383804 1.256991 0.684346 0.039 Uiso 1 1 calc R U . . .
C24 C -0.3717(2) 1.4907(2) 0.63701(6) 0.0286(3) Uani 1 1 d . . . . .
C25 C -0.2253(2) 1.4921(2) 0.46843(6) 0.0286(3) Uani 1 1 d . . . . .
C26 C -0.1740(2) 1.5196(2) 0.40605(6) 0.0301(3) Uani 1 1 d . . . . .
C27 C -0.1210(2) 1.3443(2) 0.38152(6) 0.0282(3) Uani 1 1 d . . . . .
C28 C -0.0550(2) 1.3109(2) 0.32676(6) 0.0326(3) Uani 1 1 d . . . . .
H28 H -0.038144 1.405894 0.300706 0.039 Uiso 1 1 calc R U . . .
C29 C -0.0141(2) 1.1358(2) 0.31070(6) 0.0346(3) Uani 1 1 d . . . . .
H29 H 0.033716 1.109350 0.273544 0.041 Uiso 1 1 calc R U . . .
C30 C -0.0431(2) 0.9990(2) 0.34902(6) 0.0325(3) Uani 1 1 d . . . . .
H30 H -0.018236 0.881233 0.337221 0.039 Uiso 1 1 calc R U . . .
C31 C -0.1075(2) 1.0306(2) 0.40400(6) 0.0297(3) Uani 1 1 d . . . . .
H31 H -0.126138 0.936227 0.429918 0.036 Uiso 1 1 calc R U . . .
C32 C -0.1438(2) 1.2042(2) 0.41998(6) 0.0276(3) Uani 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 C9 1.7570(14) . ?
S1 C16 1.7755(15) . ?
O1 C10 1.2153(18) . ?
N1 C1 1.3773(18) . ?
N1 C9 1.2774(19) . ?
N2 C1 1.3695(18) . ?
N2 C2 1.4553(18) . ?
N2 C3 1.3726(18) . ?
N3 C1 1.3279(18) . ?
N3 C8 1.3830(19) . ?
C3 C4 1.391(2) . ?
C3 C8 1.410(2) . ?
C4 C5 1.381(2) . ?
C5 C6 1.406(2) . ?
C6 C7 1.379(2) . ?
C7 C8 1.400(2) . ?
C9 C10 1.525(2) . ?
C10 C11 1.463(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.393(2) . ?
C14 C15 1.390(2) . ?
C15 C16 1.388(2) . ?
S2 C25 1.7555(14) . ?
S2 C32 1.7769(15) . ?
O2 C26 1.2143(18) . ?
N4 C17 1.3792(18) . ?
N4 C25 1.2827(19) . ?
N5 C17 1.3743(19) . ?
N5 C18 1.4592(18) . ?
N5 C19 1.3745(18) . ?
N6 C17 1.3255(19) . ?
N6 C24 1.3798(19) . ?
C19 C20 1.389(2) . ?
C19 C24 1.410(2) . ?
C20 C21 1.382(2) . ?
C21 C22 1.407(2) . ?
C22 C23 1.379(2) . ?
C23 C24 1.400(2) . ?
C25 C26 1.527(2) . ?
C26 C27 1.466(2) . ?
C27 C28 1.386(2) . ?
C27 C32 1.3961(19) . ?
C28 C29 1.390(2) . ?
C29 C30 1.393(2) . ?
C30 C31 1.387(2) . ?
C31 C32 1.387(2) . ?

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
C9 S1 C16 91.14(7) . . ?
C9 N1 C1 120.20(12) . . ?
C1 N2 C2 127.22(12) . . ?
C1 N2 C3 106.34(11) . . ?
C3 N2 C2 126.22(12) . . ?
C1 N3 C8 104.12(12) . . ?
N2 C1 N1 118.27(12) . . ?
N3 C1 N1 128.04(13) . . ?
N3 C1 N2 113.66(12) . . ?
N2 C3 C4 131.41(13) . . ?
N2 C3 C8 105.64(12) . . ?
C4 C3 C8 122.95(13) . . ?
C5 C4 C3 116.58(14) . . ?
C4 C5 C6 121.42(15) . . ?
C7 C6 C5 121.82(14) . . ?
C6 C7 C8 117.90(14) . . ?
N3 C8 C3 110.23(12) . . ?
N3 C8 C7 130.42(14) . . ?
C7 C8 C3 119.34(14) . . ?
N1 C9 S1 129.09(11) . . ?
N1 C9 C10 119.62(12) . . ?
C10 C9 S1 111.28(10) . . ?
O1 C10 C9 123.01(13) . . ?
O1 C10 C11 126.96(14) . . ?
C11 C10 C9 110.01(12) . . ?
C12 C11 C10 126.51(13) . . ?
C12 C11 C16 121.04(14) . . ?
C16 C11 C10 112.41(13) . . ?
C13 C12 C11 118.72(14) . . ?
C12 C13 C14 119.78(14) . . ?
C15 C14 C13 121.89(14) . . ?
C16 C15 C14 117.88(14) . . ?
C11 C16 S1 114.94(11) . . ?
C15 C16 S1 124.40(11) . . ?
C15 C16 C11 120.65(14) . . ?
C25 S2 C32 91.33(7) . . ?
C25 N4 C17 118.94(13) . . ?
C17 N5 C18 127.78(12) . . ?
C17 N5 C19 106.13(12) . . ?
C19 N5 C18 126.08(12) . . ?
C17 N6 C24 104.39(12) . . ?
N5 C17 N4 119.22(13) . . ?
N6 C17 N4 127.22(13) . . ?
N6 C17 N5 113.56(13) . . ?
N5 C19 C20 131.72(13) . . ?
N5 C19 C24 105.69(12) . . ?
C20 C19 C24 122.58(13) . . ?
C21 C20 C19 116.74(14) . . ?
C20 C21 C22 121.49(14) . . ?
C23 C22 C21 121.64(14) . . ?
C22 C23 C24 117.81(14) . . ?
N6 C24 C19 110.23(12) . . ?
N6 C24 C23 130.04(14) . . ?
C23 C24 C19 119.73(14) . . ?
N4 C25 S2 128.94(11) . . ?
N4 C25 C26 119.64(12) . . ?
C26 C25 S2 111.42(10) . . ?
O2 C26 C25 122.90(13) . . ?
O2 C26 C27 127.25(14) . . ?
C27 C26 C25 109.84(12) . . ?
C28 C27 C26 126.76(13) . . ?
C28 C27 C32 120.69(14) . . ?
C32 C27 C26 112.56(13) . . ?
C27 C28 C29 118.72(14) . . ?
C28 C29 C30 120.10(14) . . ?
C31 C30 C29 121.56(14) . . ?
C32 C31 C30 117.97(13) . . ?
C27 C32 S2 114.71(11) . . ?
C31 C32 S2 124.36(11) . . ?
C31 C32 C27 120.92(14) . . ?


_ins_header                      
;
TITL 080AM25Jialie_mPSneoVIIred in P-1 
REM P-1 (#2 in standard setting)
CELL 1.54184   7.626585   7.922528  24.437716  81.1436  82.1159  64.1257
ZERR   19.00   0.000073   0.000106   0.000275   0.0010   0.0009   0.0011
LATT  1
SFAC C H N O S
UNIT 19.00 19.00 19.00 19.00 19.00
REM  CrysAlisPro recorded range (K): Min=150.0; max=150.0; aver:150.0
TEMP -123
SIZE 0.05 0.12 0.13
TREF
HKLF 4
END
;
_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 1.485
_oxdiff_exptl_absorpt_empirical_full_min 0.717
