# Supplementary Information (SI) for RSC Advances.
# 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_rk_skvcl1
_database_code_depnum_ccdc_archive 'CCDC 2506359'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Department of Chemistry, Texas A and M University, College station, Texas, United States
United States of America
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_audit_creation_date             2024-10-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
kar@nitt.edu
nbhuv@mail.chem.tamu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C16 H16 N3 S'
_chemical_formula_sum            'C16 H16 Br N3 S'
_chemical_formula_weight         362.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16  H16  Br1  N3  S1  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   10.97500(10)
_cell_length_b                   13.76310(10)
_cell_length_c                   10.49770(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.7090(10)
_cell_angle_gamma                90
_cell_volume                     1580.33(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22385
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      78.9530
_cell_measurement_theta_min      3.1520
_shelx_estimated_absorpt_T_max   0.717
_shelx_estimated_absorpt_T_min   0.469
_exptl_absorpt_coefficient_mu    4.743
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.432
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023) 
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0314
1 0 0 0.0436
1 3 -2 0.0557
-1 -4 3 0.0709
1 -4 -3 0.0806
2 -3 -1 0.0755
4 -1 3 0.0769
1 4 4 0.0899
-1 2 1 0.0895
4 -1 -1 0.0419
-2 -1 3 0.0847
-3 0 2 0.0607
3 -2 -2 0.0472
-3 3 4 0.0814
-3 -4 0 0.0859

_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.075
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
-1.0002 0.0018 0.0005 0.0655 -0.0228 0.1226
1.0002 -0.0018 -0.0005 -0.0655 0.0228 -0.1226
1.0038 2.9935 -2.0062 -0.4317 0.1116 0.1171
-1.0053 -3.9895 3.0086 0.5888 -0.1115 -0.2147
1.0111 -3.9965 -3.0004 -0.1746 -0.5958 -0.1412
1.9872 -3.0128 -0.9842 -0.0776 -0.3082 -0.3248
3.9901 -1.0384 3.0237 0.1101 0.2665 -0.6966
1.0033 3.9776 4.0006 0.1487 0.7288 -0.1599
-0.9968 2.0038 0.9919 0.0658 0.2423 0.1582
4.0157 -1.0141 -0.9881 -0.3146 -0.0846 -0.4844
-2.0224 -0.9931 2.9932 0.4986 0.1294 0.0439
-3.0195 0.0105 1.9905 0.4066 0.1070 0.2642
3.0138 -2.0079 -1.9899 -0.3027 -0.2842 -0.3523
-3.0189 3.0049 3.9887 0.4615 0.5488 0.2904
-3.0229 -3.9826 -0.0074 0.4037 -0.4234 0.1940

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31861
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.497
_diffrn_reflns_theta_min         4.042
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  25.00   0.50    0.05    --  -47.48  92.00  -3.00  204
  2  ω    -19.00  77.00   0.50    0.05    --   47.48 -92.00-116.00  192
  3  ω    -19.00  77.00   0.50    0.05    --   47.48 -92.00-116.00  192
  4  ω    -79.00 -19.00   0.50    0.20    --  -91.75  92.00  -3.00  120
  5  ω     42.00 105.00   0.50    0.20    --  113.25 -92.00-116.00  126
  6  ω    102.00 178.00   0.50    0.20    --  113.25  92.00  -3.00  152
  7  ω    -12.00  28.00   0.50    0.05    --  -47.48  19.00 -60.00   80
  8  ω    -12.00  28.00   0.50    0.05    --  -47.48  19.00 -30.00   80
  9  ω    -12.00  28.00   0.50    0.05    --  -47.48  19.00  90.00   80
 10  ω    -27.00  12.00   0.50    0.05    --   47.48 -19.00-120.00   78
 11  ω    -27.00  12.00   0.50    0.05    --   47.48 -19.00 120.00   78
 12  ω    -49.00 -20.00   0.50    0.20    --  -91.75  45.00-150.00   58
 13  ω    -49.00 -20.00   0.50    0.20    --  -91.75  45.00-180.00   58
 14  ω   -163.00 -80.00   0.50    0.20    --  -91.75 -92.00-116.00  166
 15  ω   -163.00 -80.00   0.50    0.20    --  -91.75 -92.00-116.00  166
 16  ω    110.00 178.00   0.50    0.20    --  113.25  77.00  60.00  136
 17  ω     42.00 106.00   0.50    0.20    --  113.25 -95.00 -60.00  128
 18  ω    110.00 178.00   0.50    0.20    --  113.25  77.00-150.00  136
 19  ω     46.00 111.00   0.50    0.20    --  113.25-125.00-120.00  130
 20  ω     44.00  73.00   0.50    0.20    --  113.25 -61.00 120.00   58
 21  ω     43.00  72.00   0.50    0.20    --  113.25 -61.00  90.00   58
 22  ω    116.00 162.00   0.50    0.20    --  113.25  77.00-120.00   92
 23  ω    106.00 176.00   0.50    0.20    --  113.25  61.00 -60.00  140
 24  ω     43.00 102.00   0.50    0.20    --  113.25 -95.00  30.00  118
 25  ω    102.00 174.00   0.50    0.20    --  113.25  45.00 -30.00  144
 26  ω     77.00 103.00   0.50    0.20    --  113.25 -95.00 -30.00   52
 27  ω     50.00  75.00   0.50    0.20    --  113.25 -61.00 -60.00   50
 28  ω     42.00  75.00   0.50    0.20    --  113.25 -61.00  30.00   66
 29  ω     48.00  82.00   0.50    0.05    --   47.48  38.00-180.00   68
 30  ω    -36.00   8.00   0.50    0.05    --  -47.48  38.00-120.00   88
 31  ω     39.00  89.00   0.50    0.05    --   47.48-125.00  90.00  100
 32  ω     90.00 116.00   0.50    0.05    --   47.48  38.00-180.00   52
 33  ω    -17.00  10.00   0.50    0.05    --   47.48 -19.00   0.00   54
 34  ω    -27.00  -2.00   0.50    0.05    --   47.48 -19.00  30.00   50
 35  ω   -146.00-121.00   0.50    0.20    --  -91.75 -77.00  60.00   50
 36  ω    -46.00 -19.00   0.50    0.20    --  -91.75  61.00 -90.00   54
 37  ω   -104.00 -79.00   0.50    0.20    --  -91.75 -45.00 -90.00   50
 38  ω    121.00 164.00   0.50    0.20    --  113.25  61.00  90.00   86
 39  ω    134.00 178.00   0.50    0.20    --  113.25  45.00   0.00   88
 40  ω     47.00  74.00   0.50    0.20    --  113.25 -61.00 -90.00   54
 41  ω     43.00  71.00   0.50    0.20    --  113.25 -95.00 -90.00   56
 42  ω     63.00 106.00   0.50    0.20    --  113.25 -95.00   0.00   86
 43  ω     68.00 106.00   0.50    0.20    --  113.25 -95.00-120.00   76
 44  ω    116.00 169.00   0.50    0.20    --  113.25  77.00  30.00  106
 45  ω     81.00 106.00   0.50    0.20    --  113.25 -95.00-180.00   50
 46  ω     42.00  67.00   0.50    0.20    --  113.25 -61.00-120.00   50
 47  ω    102.00 127.00   0.50    0.20    --  113.25  30.00  60.00   50
 48  ω     63.00 111.00   0.50    0.20    --  113.25-125.00-150.00   96
 49  ω    142.00 172.00   0.50    0.20    --  113.25  15.00-180.00   60
 50  ω     80.00 106.00   0.50    0.20    --  113.25 -95.00 150.00   52
 51  ω    118.00 165.00   0.50    0.20    --  113.25  15.00  90.00   94
 52  ω     46.00  72.00   0.50    0.20    --  113.25 -61.00 -30.00   52
 53  ω     47.00  75.00   0.50    0.20    --  113.25-125.00   0.00   56
 54  ω     74.00 100.00   0.50    0.20    --  113.25 -95.00  60.00   52
 55  ω    109.00 151.00   0.50    0.20    --  113.25  61.00 120.00   84
 56  ω    129.00 176.00   0.50    0.20    --  113.25  77.00 120.00   94
 57  ω    101.00 176.00   0.50    0.20    --  113.25  15.00 150.00  150
 58  ω     35.00 120.00   0.50    0.05    --   47.48  43.00  31.10  170
 59  ω     35.00 120.00   0.50    0.05    --   47.48  47.00 112.76  170
 60  ω     35.00 119.00   0.50    0.05    --   47.48  44.00-128.06  168
 61  ω     35.00 120.00   0.50    0.05    --   47.48  46.00 -27.26  170
 62  ω     35.00 106.00   0.50    0.05    --   47.48  47.00 142.74  142
 63  ω     35.00 119.00   0.50    0.05    --   47.48  44.00 -58.16  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0655504000
_diffrn_orient_matrix_UB_12      -0.0518015000
_diffrn_orient_matrix_UB_13      0.1051085000
_diffrn_orient_matrix_UB_21      0.0230283000
_diffrn_orient_matrix_UB_22      0.0886827000
_diffrn_orient_matrix_UB_23      0.0882194000
_diffrn_orient_matrix_UB_31      -0.1225556000
_diffrn_orient_matrix_UB_32      0.0444213000
_diffrn_orient_matrix_UB_33      -0.0534107000
_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_current           '1 mA'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           '50 kV'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3132
_reflns_number_total             3223
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.855
_refine_diff_density_min         -1.021
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.074
_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)+(0.0674P)²+0.6853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0958
_refine_special_details          
;
While all other hydrogen atoms are located geometrically 
and set riding on the respective parent atoms, H1 bonded 
to N1 was located from the residual electron density 
peaks and was then set riding on N1. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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
Br1 Br 0.45547(2) 0.62951(2) 0.69631(2) 0.02926(11) Uani 1 1 d . . . . .
S1 S 0.67230(4) 0.69210(3) 0.35793(4) 0.02833(13) Uani 1 1 d . . . . .
N1 N 0.44389(16) 0.62086(12) 0.39302(16) 0.0277(4) Uani 1 1 d . . . . .
H1 H 0.451982 0.622351 0.481329 0.033 Uiso 1 1 d R U . . .
N2 N 0.34210(15) 0.58387(12) 0.32846(15) 0.0283(3) Uani 1 1 d . . . . .
N3 N 0.48363(17) 0.61890(12) 0.19703(15) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.52947(19) 0.64195(15) 0.31652(19) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.36762(17) 0.58396(13) 0.20781(18) 0.0254(4) Uani 1 1 d . . . . .
C3 C 0.5501(2) 0.62828(14) 0.0821(2) 0.0293(4) Uani 1 1 d . . . . .
H3A H 0.511602 0.586964 0.014192 0.044 Uiso 1 1 calc R U . . .
H3B H 0.635210 0.608018 0.101551 0.044 Uiso 1 1 calc R U . . .
H3C H 0.547969 0.696128 0.053655 0.044 Uiso 1 1 calc R U . . .
C4 C 0.28419(17) 0.54483(14) 0.10447(18) 0.0265(4) Uani 1 1 d . . . . .
C5 C 0.22190(18) 0.45965(15) 0.12921(18) 0.0294(4) Uani 1 1 d . . . . .
H5 H 0.235531 0.429127 0.210293 0.035 Uiso 1 1 calc R U . . .
C6 C 0.14035(19) 0.41911(16) 0.0367(2) 0.0330(4) Uani 1 1 d . . . . .
H6 H 0.097301 0.361421 0.054370 0.040 Uiso 1 1 calc R U . . .
C7 C 0.12181(19) 0.46343(17) -0.0824(2) 0.0345(4) Uani 1 1 d . . . . .
H7 H 0.066258 0.435681 -0.146508 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1840(2) 0.54782(18) -0.1080(2) 0.0371(5) Uani 1 1 d . . . . .
H8 H 0.171101 0.577407 -0.189772 0.045 Uiso 1 1 calc R U . . .
C9 C 0.26505(19) 0.58959(16) -0.01535(19) 0.0316(4) Uani 1 1 d . . . . .
H9 H 0.307023 0.647814 -0.032946 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7371(2) 0.59905(19) 0.4696(3) 0.0457(6) Uani 1 1 d . . . . .
H10A H 0.687122 0.592700 0.543483 0.055 Uiso 1 1 calc R U . . .
H10B H 0.739901 0.535238 0.426394 0.055 Uiso 1 1 calc R U . . .
C11 C 0.8640(2) 0.63307(14) 0.5126(2) 0.0307(4) Uani 1 1 d . . . . .
C12 C 0.9623(2) 0.6077(2) 0.4451(2) 0.0419(5) Uani 1 1 d . . . . .
H12 H 0.949748 0.568477 0.370689 0.050 Uiso 1 1 calc R U . . .
C13 C 1.0792(2) 0.6392(2) 0.4855(3) 0.0557(8) Uani 1 1 d . . . . .
H13 H 1.146070 0.621684 0.438309 0.067 Uiso 1 1 calc R U . . .
C14 C 1.0988(3) 0.6953(2) 0.5929(3) 0.0600(9) Uani 1 1 d . . . . .
H14 H 1.179138 0.716265 0.620629 0.072 Uiso 1 1 calc R U . . .
C15 C 1.0019(3) 0.72099(19) 0.6601(3) 0.0553(7) Uani 1 1 d . . . . .
H15 H 1.015393 0.759699 0.734864 0.066 Uiso 1 1 calc R U . . .
C16 C 0.8844(2) 0.69115(16) 0.6202(2) 0.0389(5) Uani 1 1 d . . . . .
H16 H 0.817751 0.710501 0.666608 0.047 Uiso 1 1 calc R U . . .


_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 C1 1.735(2) . ?
S1 C10 1.839(2) . ?
N1 H1 0.9242 . ?
N1 N2 1.357(2) . ?
N1 C1 1.317(3) . ?
N2 C2 1.319(2) . ?
N3 C1 1.350(3) . ?
N3 C2 1.374(3) . ?
N3 C3 1.466(3) . ?
C2 C4 1.464(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.392(3) . ?
C4 C9 1.401(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.504(3) . ?
C11 C12 1.384(3) . ?
C11 C16 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.369(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(4) . ?
C16 H16 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
C1 S1 C10 100.18(10) . . ?
N2 N1 H1 121.1 . . ?
C1 N1 H1 126.3 . . ?
C1 N1 N2 112.16(16) . . ?
C2 N2 N1 104.36(16) . . ?
C1 N3 C2 106.43(17) . . ?
C1 N3 C3 124.83(19) . . ?
C2 N3 C3 128.72(17) . . ?
N1 C1 S1 127.57(15) . . ?
N1 C1 N3 106.53(18) . . ?
N3 C1 S1 125.89(17) . . ?
N2 C2 N3 110.52(17) . . ?
N2 C2 C4 122.82(17) . . ?
N3 C2 C4 126.53(17) . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 117.29(17) . . ?
C5 C4 C9 119.87(19) . . ?
C9 C4 C2 122.84(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.54(19) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.5(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.26(19) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.62(19) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 H9 120.4 . . ?
C8 C9 C4 119.2(2) . . ?
C8 C9 H9 120.4 . . ?
S1 C10 H10A 110.5 . . ?
S1 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 S1 105.96(15) . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 C16 118.8(2) . . ?
C16 C11 C10 120.6(2) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.5(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 119.9 . . ?

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 C12 -89.0(2) . . . . ?
S1 C10 C11 C16 90.4(2) . . . . ?
N1 N2 C2 N3 0.9(2) . . . . ?
N1 N2 C2 C4 176.79(17) . . . . ?
N2 N1 C1 S1 178.94(15) . . . . ?
N2 N1 C1 N3 0.3(2) . . . . ?
N2 C2 C4 C5 -39.7(3) . . . . ?
N2 C2 C4 C9 139.9(2) . . . . ?
N3 C2 C4 C5 135.5(2) . . . . ?
N3 C2 C4 C9 -44.8(3) . . . . ?
C1 S1 C10 C11 179.28(18) . . . . ?
C1 N1 N2 C2 -0.7(2) . . . . ?
C1 N3 C2 N2 -0.7(2) . . . . ?
C1 N3 C2 C4 -176.46(18) . . . . ?
C2 N3 C1 S1 -178.41(15) . . . . ?
C2 N3 C1 N1 0.3(2) . . . . ?
C2 C4 C5 C6 179.15(18) . . . . ?
C2 C4 C9 C8 -179.81(19) . . . . ?
C3 N3 C1 S1 3.1(3) . . . . ?
C3 N3 C1 N1 -178.22(16) . . . . ?
C3 N3 C2 N2 177.66(18) . . . . ?
C3 N3 C2 C4 1.9(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C4 C9 C8 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C4 0.6(3) . . . . ?
C9 C4 C5 C6 -0.5(3) . . . . ?
C10 S1 C1 N1 59.8(2) . . . . ?
C10 S1 C1 N3 -121.8(2) . . . . ?
C10 C11 C12 C13 -179.9(2) . . . . ?
C10 C11 C16 C15 179.1(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C11 C16 C15 -1.4(3) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C11 1.3(4) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?

_olex2_submission_original_sample_id RKB_241015_Rc_SKVCL1
_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 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.669
####################################################################### 
# 
# 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_rk_skvtlsd
_database_code_depnum_ccdc_archive 'CCDC 2506371'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Department of Chemistry, Texas A and M University, College station, Texas, United States
United States of America
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_audit_creation_date             2024-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
kar@nitt.edu
nbhuv@mail.chem.tamu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N4 O2 S'
_chemical_formula_sum            'C16 H16 N4 O2 S'
_chemical_formula_weight         328.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H16N4O2S
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.24200(10)
_cell_length_b                   4.94600(10)
_cell_length_c                   17.0656(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.8380(10)
_cell_angle_gamma                90
_cell_volume                     780.00(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12123
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.5650
_cell_measurement_theta_min      2.5620
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.440
_exptl_absorpt_coefficient_mu    1.979
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023) 
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    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0320
0 0 1 0.0208
-1 0 0 0.0181
1 0 0 0.0250
0 -1 0 0.2500
0 1 0 0.2471

_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.043
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
-0.0006 0.0003 -0.9997 -0.0284 0.0845 0.0140
0.0006 -0.0003 0.9997 0.0284 -0.0845 -0.0140
-0.9993 -0.0009 0.0025 -0.1562 -0.0536 0.0218
0.9993 0.0009 -0.0025 0.1562 0.0536 -0.0218
-0.0005 -1.0002 0.0065 -0.0540 0.0316 -0.3052
0.0005 1.0002 -0.0065 0.0540 -0.0316 0.3052

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14972
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.431
_diffrn_reflns_theta_min         2.589
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  29.00   0.50    0.10    --  -46.62  19.00  30.00   82
  2  ω    -49.00 -23.00   0.50    0.40    --  -91.75  45.00  30.00   52
  3  ω    -12.00  29.00   0.50    0.10    --  -46.62  19.00 -60.00   82
  4  ω     -6.00  30.00   0.50    0.10    --  -46.62  15.00-125.00   72
  5  ω     32.00 120.00   0.50    0.10    --   46.62  38.00 -60.00  176
  6  ω     32.00 120.00   0.50    0.10    --   46.62  38.00 -60.00  176
  7  ω     32.00 120.00   0.50    0.10    --   46.62  38.00  30.00  176
  8  ω     29.00 123.00   0.50    0.10    --   46.62  15.00-125.00  188
  9  ω     96.00 176.00   0.50    0.40    --  113.25  15.00-125.00  160
 10  ω    143.00 169.00   0.50    0.40    --  113.25  61.00 -60.00   52
 11  ω    112.00 167.00   0.50    0.40    --  113.25  77.00   0.00  110
 12  ω    109.00 135.00   0.50    0.40    --  113.25  61.00 -60.00   52
 13  ω    108.00 134.00   0.50    0.40    --  113.25  61.00  30.00   52
 14  ω    121.00 147.00   0.50    0.40    --  113.25  77.00  60.00   52
 15  ω    147.00 178.00   0.50    0.40    --  113.25  77.00 120.00   62
 16  ω    117.00 142.00   0.50    0.40    --  113.25  77.00 120.00   50
 17  ω    118.00 177.00   0.50    0.40    --  113.25  61.00 -30.00  118
 18  ω    101.00 126.00   0.50    0.40    --  113.25  45.00 -60.00   50
 19  ω     99.00 133.00   0.50    0.40    --  113.25  45.00 -90.00   68
 20  ω    145.00 178.00   0.50    0.40    --  113.25  45.00 -90.00   66
 21  ω    108.00 134.00   0.50    0.40    --  113.25  45.00 -30.00   52
 22  ω    103.00 128.00   0.50    0.40    --  113.25  30.00   0.00   50
 23  ω    102.00 128.00   0.50    0.40    --  113.25  30.00  30.00   52
 24  ω    105.00 131.00   0.50    0.40    --  113.25  45.00  60.00   52
 25  ω    147.00 177.00   0.50    0.40    --  113.25  45.00  60.00   60
 26  ω    144.00 175.00   0.50    0.40    --  113.25  15.00 -60.00   62
 27  ω     96.00 176.00   0.50    0.40    --  113.25  15.00-125.00  160
 28  ω     47.00  74.00   0.50    0.40    --  113.25 -61.00-180.00   54
 29  ω     43.00  75.00   0.50    0.40    --  113.25 -61.00-120.00   64
 30  ω     41.00  74.00   0.50    0.40    --  113.25 -61.00 -60.00   66
 31  ω     41.00  75.00   0.50    0.40    --  113.25 -61.00   0.00   68
 32  ω    -28.00   6.00   0.50    0.10    --   46.62 -15.00  63.00   68
 33  ω     42.00  71.00   0.50    0.40    --  113.25 -61.00 120.00   58
 34  ω     41.00  74.00   0.50    0.40    --  113.25 -61.00  90.00   66
 35  ω     47.00  73.00   0.50    0.40    --  113.25 -95.00 150.00   52
 36  ω     50.00  90.00   0.50    0.40    --  113.25-125.00  90.00   80
 37  ω     66.00 103.00   0.50    0.40    --  113.25 -95.00   0.00   74
 38  ω     64.00 105.00   0.50    0.40    --  113.25 -95.00 -30.00   82
 39  ω     67.00 109.00   0.50    0.40    --  113.25-125.00 -30.00   84
 40  ω     34.00  93.00   0.50    0.10    --   46.62-125.00-120.00  118
 41  ω   -122.00 -29.00   0.50    0.10    --  -46.62 -15.00  63.00  186
 42  ω   -119.00 -31.00   0.50    0.10    --  -46.62 -46.00 -51.70  176
 43  ω   -118.00 -31.00   0.50    0.10    --  -46.62 -47.00-110.98  174
 44  ω   -119.00 -31.00   0.50    0.10    --  -46.62 -46.00 -51.70  176
 45  ω   -119.00 -31.00   0.50    0.10    --  -46.62 -44.00-153.17  176
 46  ω    -47.00 -22.00   0.50    0.40    --  -91.75 125.00 -60.00   50
 47  ω    -85.00 -22.00   0.50    0.40    --  -91.75 125.00 -60.00  126
 48  ω   -167.00 -74.00   0.50    0.40    --  -91.75 -15.00  63.00  186
 49  ω   -107.00 -81.00   0.50    0.40    --  -91.75 -47.00  12.76   52
 50  ω   -103.00 -77.00   0.50    0.40    --  -91.75 -46.00   2.82   52
 51  ω   -103.00 -77.00   0.50    0.40    --  -91.75 -46.00  -0.70   52
 52  ω   -110.00 -84.00   0.50    0.40    --  -91.75 -47.00 -77.05   52
 53  ω   -114.00 -88.00   0.50    0.40    --  -91.75 -48.00 -95.51   52
 54  ω   -117.00 -79.00   0.50    0.40    --  -91.75 -45.00-120.00   76
 55  ω   -115.00 -86.00   0.50    0.40    --  -91.75 -47.00 -64.23   58
 56  ω   -111.00 -85.00   0.50    0.40    --  -91.75 -45.00 -60.00   52
 57  ω   -164.00 -77.00   0.50    0.40    --  -91.75 -45.00 -90.00  174
 58  ω   -164.00 -77.00   0.50    0.40    --  -91.75 -45.00 -34.44  174
 59  ω   -102.00 -77.00   0.50    0.40    --  -91.75 -42.00 -54.19   50
 60  ω   -104.00 -77.00   0.50    0.40    --  -91.75 -45.00 -19.54   54
 61  ω   -102.00 -77.00   0.50    0.40    --  -91.75 -37.00  -0.96   50
 62  ω   -164.00-138.00   0.50    0.40    --  -91.75 -37.00  -0.96   52
 63  ω   -104.00 -78.00   0.50    0.40    --  -91.75 -37.00-145.83   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1563599000
_diffrn_orient_matrix_UB_12      0.0541265000
_diffrn_orient_matrix_UB_13      0.0283589000
_diffrn_orient_matrix_UB_21      0.0534679000
_diffrn_orient_matrix_UB_22      -0.0321241000
_diffrn_orient_matrix_UB_23      -0.0845707000
_diffrn_orient_matrix_UB_31      -0.0221250000
_diffrn_orient_matrix_UB_32      0.3050690000
_diffrn_orient_matrix_UB_33      -0.0138652000
_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_current           '1 mA'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           '50 kV'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                2933
_reflns_number_total             2972
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.054
_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)+(0.0401P)²+0.1496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0642
_refine_special_details          
;
Hydrogen atom on N3 was located from the difference Fourier maps 
and was set riding on the parent atom.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.66561(4) 0.97908(10) 0.72238(2) 0.01885(12) Uani 1 1 d . . . . .
O1 O -0.00354(14) -0.3750(3) 0.82477(8) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.03872(15) -0.2663(3) 0.70446(7) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.63720(15) 0.8549(4) 0.87548(8) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.54156(15) 0.6790(3) 0.83832(9) 0.0183(3) Uani 1 1 d . . . . .
N3 N 0.80202(16) 1.1861(3) 0.84958(8) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.836998 1.312698 0.817831 0.022 Uiso 1 1 d R U . . .
N4 N 0.05841(15) -0.2380(3) 0.77523(8) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.70301(17) 1.0067(4) 0.82397(9) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.46565(18) 0.5387(4) 0.88557(10) 0.0184(4) Uani 1 1 d . . . . .
H2 H 0.478362 0.561793 0.940499 0.022 Uiso 1 1 calc R U . . .
C3 C 0.35978(17) 0.3435(4) 0.85585(9) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.28078(18) 0.1893(4) 0.90903(10) 0.0177(4) Uani 1 1 d . . . . .
H4 H 0.295650 0.214827 0.963734 0.021 Uiso 1 1 calc R U . . .
C5 C 0.18126(17) 0.0000(5) 0.88270(9) 0.0180(3) Uani 1 1 d . . . . .
H5 H 0.128191 -0.105944 0.918744 0.022 Uiso 1 1 calc R U . . .
C6 C 0.16054(16) -0.0319(4) 0.80263(9) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.23596(19) 0.1196(4) 0.74798(10) 0.0187(4) Uani 1 1 d . . . . .
H7 H 0.219298 0.094721 0.693385 0.022 Uiso 1 1 calc R U . . .
C8 C 0.33563(18) 0.3069(4) 0.77502(10) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.388383 0.412072 0.738646 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8269(2) 1.2246(5) 0.93282(10) 0.0228(4) Uani 1 1 d . . . . .
H9A H 0.897267 1.370467 0.941065 0.034 Uiso 1 1 calc R U . . .
H9B H 0.864675 1.056979 0.955893 0.034 Uiso 1 1 calc R U . . .
H9C H 0.735613 1.272484 0.957811 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7864(2) 1.2317(4) 0.68029(10) 0.0201(4) Uani 1 1 d . . . . .
H10A H 0.761573 1.414630 0.699395 0.024 Uiso 1 1 calc R U . . .
H10B H 0.888229 1.192358 0.695059 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7655(2) 1.2151(4) 0.59258(10) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.8467(2) 1.0340(4) 0.54860(11) 0.0268(5) Uani 1 1 d . . . . .
H12 H 0.917214 0.922784 0.573639 0.032 Uiso 1 1 calc R U . . .
C13 C 0.8241(2) 1.0167(6) 0.46795(11) 0.0324(5) Uani 1 1 d . . . . .
H13 H 0.879783 0.894018 0.437965 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7212(2) 1.1768(5) 0.43132(11) 0.0308(5) Uani 1 1 d . . . . .
H14 H 0.705698 1.163079 0.376304 0.037 Uiso 1 1 calc R U . . .
C15 C 0.6405(2) 1.3574(5) 0.47465(12) 0.0316(5) Uani 1 1 d . . . . .
H15 H 0.569754 1.467806 0.449424 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6631(2) 1.3768(5) 0.55513(11) 0.0274(4) Uani 1 1 d . . . . .
H16 H 0.608130 1.501622 0.584723 0.033 Uiso 1 1 calc R U . . .


_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 C1 1.7681(16) . ?
S1 C10 1.8292(19) . ?
O1 N4 1.231(2) . ?
O2 N4 1.2268(19) . ?
N1 N2 1.387(2) . ?
N1 C1 1.312(2) . ?
N2 C2 1.281(2) . ?
N3 H3 0.8919 . ?
N3 C1 1.343(2) . ?
N3 C9 1.448(2) . ?
N4 C6 1.461(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.460(2) . ?
C3 C4 1.399(2) . ?
C3 C8 1.406(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C7 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.509(2) . ?
C11 C12 1.394(3) . ?
C11 C16 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 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
C1 S1 C10 102.74(9) . . ?
C1 N1 N2 110.55(14) . . ?
C2 N2 N1 113.80(14) . . ?
C1 N3 H3 121.2 . . ?
C1 N3 C9 120.25(15) . . ?
C9 N3 H3 116.7 . . ?
O1 N4 C6 117.97(14) . . ?
O2 N4 O1 123.32(16) . . ?
O2 N4 C6 118.71(14) . . ?
N1 C1 S1 121.79(14) . . ?
N1 C1 N3 118.69(15) . . ?
N3 C1 S1 119.51(13) . . ?
N2 C2 H2 119.7 . . ?
N2 C2 C3 120.67(16) . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.24(15) . . ?
C4 C3 C8 119.30(17) . . ?
C8 C3 C2 121.45(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.60(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.63(16) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 N4 118.30(16) . . ?
C5 C6 C7 122.43(17) . . ?
C7 C6 N4 119.24(15) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.38(15) . . ?
C8 C7 H7 120.8 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.65(16) . . ?
C7 C8 H8 119.7 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S1 C10 H10A 110.4 . . ?
S1 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 S1 106.41(13) . . ?
C11 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
C12 C11 C10 120.45(17) . . ?
C16 C11 C10 120.16(18) . . ?
C16 C11 C12 119.38(17) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.87(19) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.08(18) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

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 C12 -87.63(19) . . . . ?
S1 C10 C11 C16 91.1(2) . . . . ?
O1 N4 C6 C5 -0.6(2) . . . . ?
O1 N4 C6 C7 177.75(17) . . . . ?
O2 N4 C6 C5 179.52(17) . . . . ?
O2 N4 C6 C7 -2.2(3) . . . . ?
N1 N2 C2 C3 -179.94(16) . . . . ?
N2 N1 C1 S1 0.8(2) . . . . ?
N2 N1 C1 N3 -178.71(16) . . . . ?
N2 C2 C3 C4 178.66(17) . . . . ?
N2 C2 C3 C8 -1.3(3) . . . . ?
N4 C6 C7 C8 -177.81(17) . . . . ?
C1 S1 C10 C11 178.00(13) . . . . ?
C1 N1 N2 C2 -175.07(16) . . . . ?
C2 C3 C4 C5 -179.06(17) . . . . ?
C2 C3 C8 C7 179.41(17) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
C4 C5 C6 N4 178.17(16) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C8 C3 C4 C5 0.9(3) . . . . ?
C9 N3 C1 S1 175.75(14) . . . . ?
C9 N3 C1 N1 -4.7(3) . . . . ?
C10 S1 C1 N1 -179.73(16) . . . . ?
C10 S1 C1 N3 -0.19(17) . . . . ?
C10 C11 C12 C13 178.61(19) . . . . ?
C10 C11 C16 C15 -178.22(19) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder'
_olex2_submission_original_sample_id RKB_240705_SDc_SKVTLSD
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.869
####################################################################### 
# 
# 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_rk_tl1a
_database_code_depnum_ccdc_archive 'CCDC 2506364'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Department of Chemistry, Texas A and M University, College station, Texas, United States
United States of America
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_audit_creation_date             2023-10-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
nbhuv@mail.chem.tamu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N3 S'
_chemical_formula_sum            'C16 H17 N3 S'
_chemical_formula_weight         283.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H17N3S
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   24.8331(2)
_cell_length_b                   11.78700(10)
_cell_length_c                   10.07740(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.8390(10)
_cell_angle_gamma                90
_cell_volume                     2946.11(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13765
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.5230
_cell_measurement_theta_min      3.5620
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.585
_exptl_absorpt_coefficient_mu    1.884
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.68a (Rigaku Oxford Diffraction, 2023)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0410
-1 0 0 0.0410
0 0 1 0.1161
0 0 -1 0.1161
1 -1 0 0.1265
-1 1 0 0.1265

_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.082
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 -0.0000 -0.0000 -0.0620 -0.0033 0.0021
-1.0000 0.0000 0.0000 0.0620 0.0033 -0.0021
0.0000 0.0000 1.0000 -0.0026 0.0058 0.1529
-0.0000 -0.0000 -1.0000 0.0026 -0.0058 -0.1529
1.0000 -1.0000 0.0000 -0.0690 0.1272 -0.0029
-1.0000 1.0000 -0.0000 0.0690 -0.1272 0.0029

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21509
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.874
_diffrn_reflns_theta_min         3.564
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     50.00  75.00   0.50    0.05    --   47.69-141.00-115.00   50
  2  ω     60.00 110.00   0.50    0.09    --  113.25-141.00-115.00  100
  3  ω     38.00  95.00   0.50    0.05    --   47.69-130.00  57.00  114
  4  ω     45.00  80.00   0.50    0.09    --  113.25-126.00 150.00   70
  5  ω     88.00 113.00   0.50    0.09    --  113.25-126.00 150.00   50
  6  ω     49.00 113.00   0.50    0.09    --  113.25-126.00 120.00  128
  7  ω     50.00 116.00   0.50    0.09    --  113.25-130.00  57.00  132
  8  ω     79.00 105.00   0.50    0.09    --  113.25 -95.00  30.00   52
  9  ω     53.00 113.00   0.50    0.09    --  113.25-126.00-180.00  120
 10  ω     -8.00  25.00   0.50    0.05    --   47.69 -19.00 -60.00   66
 11  ω     46.00  71.00   0.50    0.09    --  113.25 -61.00 -60.00   50
 12  ω     44.00  71.00   0.50    0.09    --  113.25 -61.00  90.00   54
 13  ω     44.00  70.00   0.50    0.09    --  113.25 -61.00 120.00   52
 14  ω     42.00  70.00   0.50    0.09    --  113.25 -61.00  30.00   56
 15  ω     96.00 145.00   0.50    0.09    --  113.25 126.00-150.00   98
 16  ω     99.00 125.00   0.50    0.09    --  113.25 130.00 129.00   52
 17  ω    148.00 175.00   0.50    0.09    --  113.25  45.00 120.00   54
 18  ω    101.00 142.00   0.50    0.09    --  113.25  45.00 120.00   82
 19  ω    101.00 136.00   0.50    0.09    --  113.25  30.00  60.00   70
 20  ω    140.00 166.00   0.50    0.09    --  113.25  30.00  60.00   52
 21  ω    104.00 172.00   0.50    0.09    --  113.25  45.00-150.00  136
 22  ω    -26.00  28.00   0.50    0.05    --  -47.69  19.00 -30.00  108
 23  ω    -75.00 -46.00   0.50    0.05    --  -47.69 130.00 129.00   58
 24  ω    -49.00 -22.00   0.50    0.09    --  -91.75  45.00   0.00   54
 25  ω    -43.00  24.00   0.50    0.05    --  -47.69  38.00 -90.00  134
 26  ω   -148.00 -71.00   0.50    0.09    --  -91.75-130.00  57.00  154
 27  ω   -117.00 -81.00   0.50    0.05    --  -47.69-130.00  57.00   72
 28  ω   -102.00 -70.00   0.50    0.05    --  -47.69-141.00-115.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0619824000
_diffrn_orient_matrix_UB_12      0.0070307000
_diffrn_orient_matrix_UB_13      -0.0025504000
_diffrn_orient_matrix_UB_21      -0.0032687000
_diffrn_orient_matrix_UB_22      -0.1304491000
_diffrn_orient_matrix_UB_23      0.0058450000
_diffrn_orient_matrix_UB_31      0.0021198000
_diffrn_orient_matrix_UB_32      0.0050641000
_diffrn_orient_matrix_UB_33      0.1528994000
_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_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5643
_reflns_number_total             6206
_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 1.171.43.68a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.101a 64-bit (release 31-08-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.68a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.082
_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)+(0.0498P)²+0.6852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0968
_refine_special_details          
;
Compound crystallized in the spacegroup P21/c with Z=8, 
Z'-2. 

Atoms C2-C6 indicated elongated thermal ellipsoids suggesting 
possible minor disorder. No efforts were made to model the 
latter. 

CHECKCIF detects pseudo symmetry. However, our trials 
to find a smaller unit cell was unsuccessful. Also, overlay 
of the two molecules of the asymmetric unit does not match 
100 percent. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7B(H7BA,H7BB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), N1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B),
  C6B(H6B), C10B(H10B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B),
 C16B(H16B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC)
;
_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 0.08996(2) 0.55322(2) -0.00791(3) 0.02237(9) Uani 1 1 d . . . . .
N1 N 0.04555(4) 0.75831(9) -0.06447(10) 0.0243(2) Uani 1 1 d . . . . .
H1 H 0.027490 0.723241 -0.129661 0.029 Uiso 1 1 calc R U . . .
N2 N 0.09861(4) 0.74764(9) 0.12827(10) 0.0256(2) Uani 1 1 d . . . . .
N3 N 0.12944(4) 0.67067(9) 0.20655(10) 0.0241(2) Uani 1 1 d . . . . .
C1 C 0.07409(5) 0.41217(10) -0.21410(11) 0.0223(2) Uani 1 1 d . . . . .
C2 C 0.05598(6) 0.31335(12) -0.15532(14) 0.0325(3) Uani 1 1 d . . . . .
H2 H 0.031043 0.317503 -0.086969 0.039 Uiso 1 1 calc R U . . .
C3 C 0.07454(8) 0.20819(13) -0.19704(17) 0.0465(4) Uani 1 1 d . . . . .
H3 H 0.062172 0.140784 -0.156785 0.056 Uiso 1 1 calc R U . . .
C4 C 0.11085(8) 0.20124(13) -0.29669(16) 0.0483(5) Uani 1 1 d . . . . .
H4 H 0.123226 0.129387 -0.325127 0.058 Uiso 1 1 calc R U . . .
C5 C 0.12885(7) 0.29894(14) -0.35412(15) 0.0424(4) Uani 1 1 d . . . . .
H5 H 0.153691 0.294300 -0.422637 0.051 Uiso 1 1 calc R U . . .
C6 C 0.11115(6) 0.40429(12) -0.31319(13) 0.0295(3) Uani 1 1 d . . . . .
H6 H 0.124317 0.471277 -0.352780 0.035 Uiso 1 1 calc R U . . .
C7 C 0.05525(5) 0.52697(11) -0.16936(11) 0.0226(2) Uani 1 1 d . . . . .
H7A H 0.015698 0.527068 -0.161047 0.027 Uiso 1 1 calc R U . . .
H7B H 0.064582 0.586217 -0.233957 0.027 Uiso 1 1 calc R U . . .
C8 C 0.07741(5) 0.69846(10) 0.02273(11) 0.0217(2) Uani 1 1 d . . . . .
C9 C 0.04117(6) 0.88043(12) -0.05051(14) 0.0354(3) Uani 1 1 d . . . . .
H9A H 0.019276 0.911178 -0.125716 0.053 Uiso 1 1 calc R U . . .
H9B H 0.077223 0.914343 -0.048899 0.053 Uiso 1 1 calc R U . . .
H9C H 0.024034 0.898254 0.032514 0.053 Uiso 1 1 calc R U . . .
C10 C 0.16018(5) 0.71929(11) 0.29468(12) 0.0245(3) Uani 1 1 d . . . . .
H10 H 0.160927 0.799838 0.297686 0.029 Uiso 1 1 calc R U . . .
C11 C 0.19426(5) 0.65575(11) 0.39115(12) 0.0236(3) Uani 1 1 d . . . . .
C12 C 0.19528(6) 0.53760(12) 0.39539(13) 0.0310(3) Uani 1 1 d . . . . .
H12 H 0.173415 0.495069 0.333424 0.037 Uiso 1 1 calc R U . . .
C13 C 0.22804(6) 0.48201(14) 0.48953(15) 0.0388(3) Uani 1 1 d . . . . .
H13 H 0.228710 0.401439 0.491070 0.047 Uiso 1 1 calc R U . . .
C14 C 0.25980(6) 0.54229(15) 0.58139(14) 0.0383(4) Uani 1 1 d . . . . .
H14 H 0.282116 0.503369 0.645750 0.046 Uiso 1 1 calc R U . . .
C15 C 0.25890(6) 0.65934(16) 0.57901(14) 0.0405(4) Uani 1 1 d . . . . .
H15 H 0.280300 0.701330 0.642459 0.049 Uiso 1 1 calc R U . . .
C16 C 0.22662(6) 0.71566(13) 0.48360(14) 0.0343(3) Uani 1 1 d . . . . .
H16 H 0.226636 0.796238 0.481430 0.041 Uiso 1 1 calc R U . . .
S1B S 0.41259(2) 0.45890(2) 0.49792(3) 0.02164(9) Uani 1 1 d . . . . .
N1B N 0.47354(4) 0.26818(9) 0.53137(10) 0.0234(2) Uani 1 1 d . . . . .
H1B H 0.490294 0.304126 0.597893 0.028 Uiso 1 1 calc R U . . .
N2B N 0.42054(4) 0.27784(9) 0.33903(10) 0.0218(2) Uani 1 1 d . . . . .
N3B N 0.38117(4) 0.34557(9) 0.27286(10) 0.0216(2) Uani 1 1 d . . . . .
C1B C 0.41492(5) 0.57609(11) 0.72826(11) 0.0222(2) Uani 1 1 d . . . . .
C2B C 0.37961(5) 0.55470(11) 0.82825(12) 0.0267(3) Uani 1 1 d . . . . .
H2B H 0.372584 0.478741 0.853736 0.032 Uiso 1 1 calc R U . . .
C3B C 0.35457(6) 0.64381(13) 0.89100(13) 0.0321(3) Uani 1 1 d . . . . .
H3B H 0.330752 0.628447 0.959702 0.038 Uiso 1 1 calc R U . . .
C4B C 0.36412(6) 0.75521(12) 0.85401(13) 0.0321(3) Uani 1 1 d . . . . .
H4B H 0.347242 0.815984 0.897850 0.039 Uiso 1 1 calc R U . . .
C5B C 0.39847(6) 0.77721(12) 0.75260(13) 0.0308(3) Uani 1 1 d . . . . .
H5B H 0.404837 0.853213 0.726184 0.037 Uiso 1 1 calc R U . . .
C6B C 0.42358(5) 0.68814(11) 0.68963(12) 0.0261(3) Uani 1 1 d . . . . .
H6B H 0.446826 0.703623 0.619764 0.031 Uiso 1 1 calc R U . . .
C7B C 0.44405(5) 0.47954(11) 0.66453(11) 0.0233(2) Uani 1 1 d . . . . .
H7BA H 0.440976 0.409520 0.717877 0.028 Uiso 1 1 calc R U . . .
H7BB H 0.482748 0.498083 0.658700 0.028 Uiso 1 1 calc R U . . .
C8B C 0.43748(5) 0.32426(10) 0.45034(11) 0.0201(2) Uani 1 1 d . . . . .
C9B C 0.48468(5) 0.14877(11) 0.50890(13) 0.0277(3) Uani 1 1 d . . . . .
H9BA H 0.512078 0.122285 0.575101 0.042 Uiso 1 1 calc R U . . .
H9BB H 0.497946 0.138873 0.419647 0.042 Uiso 1 1 calc R U . . .
H9BC H 0.451535 0.104690 0.516804 0.042 Uiso 1 1 calc R U . . .
C10B C 0.35681(5) 0.29452(10) 0.17543(11) 0.0210(2) Uani 1 1 d . . . . .
H10B H 0.368529 0.220650 0.152563 0.025 Uiso 1 1 calc R U . . .
C11B C 0.31167(5) 0.34498(10) 0.09768(11) 0.0208(2) Uani 1 1 d . . . . .
C12B C 0.28231(5) 0.43707(11) 0.14435(12) 0.0259(3) Uani 1 1 d . . . . .
H12B H 0.292698 0.471578 0.226879 0.031 Uiso 1 1 calc R U . . .
C13B C 0.23803(6) 0.47760(12) 0.06954(13) 0.0305(3) Uani 1 1 d . . . . .
H13B H 0.217520 0.538562 0.102441 0.037 Uiso 1 1 calc R U . . .
C14B C 0.22340(5) 0.42990(13) -0.05300(13) 0.0311(3) Uani 1 1 d . . . . .
H14B H 0.193621 0.459651 -0.104649 0.037 Uiso 1 1 calc R U . . .
C15B C 0.25220(5) 0.33902(13) -0.09988(13) 0.0296(3) Uani 1 1 d . . . . .
H15B H 0.242296 0.306368 -0.183760 0.036 Uiso 1 1 calc R U . . .
C16B C 0.29570(5) 0.29566(11) -0.02376(12) 0.0253(3) Uani 1 1 d . . . . .
H16B H 0.314725 0.231798 -0.054809 0.030 Uiso 1 1 calc R U . . .


_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 C7 1.8294(12) . ?
S1 C8 1.7699(12) . ?
N1 H1 0.8800 . ?
N1 C8 1.3516(15) . ?
N1 C9 1.4509(16) . ?
N2 N3 1.4043(14) . ?
N2 C8 1.2997(16) . ?
N3 C10 1.2777(16) . ?
C1 C2 1.3916(18) . ?
C1 C6 1.3941(18) . ?
C1 C7 1.5079(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.4632(17) . ?
C11 C12 1.3935(19) . ?
C11 C16 1.3922(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3837(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
S1B C7B 1.8327(11) . ?
S1B C8B 1.7776(12) . ?
N1B H1B 0.8800 . ?
N1B C8B 1.3539(15) . ?
N1B C9B 1.4544(16) . ?
N2B N3B 1.4047(13) . ?
N2B C8B 1.2992(15) . ?
N3B C10B 1.2779(15) . ?
C1B C2B 1.3911(18) . ?
C1B C6B 1.3966(17) . ?
C1B C7B 1.5090(17) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.389(2) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.389(2) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.388(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3903(19) . ?
C6B H6B 0.9500 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B H10B 0.9500 . ?
C10B C11B 1.4619(16) . ?
C11B C12B 1.4018(17) . ?
C11B C16B 1.3946(17) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.3868(18) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.389(2) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.384(2) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.3907(17) . ?
C16B H16B 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 C7 103.86(6) . . ?
C8 N1 H1 120.0 . . ?
C8 N1 C9 119.94(10) . . ?
C9 N1 H1 120.0 . . ?
C8 N2 N3 111.04(10) . . ?
C10 N3 N2 113.01(10) . . ?
C2 C1 C6 119.20(12) . . ?
C2 C1 C7 120.81(12) . . ?
C6 C1 C7 119.97(11) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.80(15) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.53(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.54(14) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.72(16) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.19(14) . . ?
C5 C6 H6 119.9 . . ?
S1 C7 H7A 110.5 . . ?
S1 C7 H7B 110.5 . . ?
C1 C7 S1 106.15(8) . . ?
C1 C7 H7A 110.5 . . ?
C1 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
N1 C8 S1 119.59(9) . . ?
N2 C8 S1 120.43(9) . . ?
N2 C8 N1 119.98(11) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 118.7 . . ?
N3 C10 C11 122.56(12) . . ?
C11 C10 H10 118.7 . . ?
C12 C11 C10 122.75(11) . . ?
C16 C11 C10 118.73(12) . . ?
C16 C11 C12 118.51(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.23(13) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.82(14) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.59(13) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.86(14) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.98(14) . . ?
C15 C16 H16 119.5 . . ?
C8B S1B C7B 103.15(6) . . ?
C8B N1B H1B 119.9 . . ?
C8B N1B C9B 120.25(10) . . ?
C9B N1B H1B 119.9 . . ?
C8B N2B N3B 111.01(10) . . ?
C10B N3B N2B 112.89(10) . . ?
C2B C1B C6B 118.98(12) . . ?
C2B C1B C7B 120.29(11) . . ?
C6B C1B C7B 120.72(11) . . ?
C1B C2B H2B 119.8 . . ?
C3B C2B C1B 120.35(12) . . ?
C3B C2B H2B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C4B C3B C2B 120.44(13) . . ?
C4B C3B H3B 119.8 . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B C3B 119.60(13) . . ?
C5B C4B H4B 120.2 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.06(13) . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B H6B 119.7 . . ?
C5B C6B C1B 120.54(12) . . ?
C5B C6B H6B 119.7 . . ?
S1B C7B H7BA 110.2 . . ?
S1B C7B H7BB 110.2 . . ?
C1B C7B S1B 107.36(8) . . ?
C1B C7B H7BA 110.2 . . ?
C1B C7B H7BB 110.2 . . ?
H7BA C7B H7BB 108.5 . . ?
N1B C8B S1B 120.10(9) . . ?
N2B C8B S1B 120.45(9) . . ?
N2B C8B N1B 119.43(11) . . ?
N1B C9B H9BA 109.5 . . ?
N1B C9B H9BB 109.5 . . ?
N1B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
N3B C10B H10B 118.6 . . ?
N3B C10B C11B 122.77(11) . . ?
C11B C10B H10B 118.6 . . ?
C12B C11B C10B 122.21(11) . . ?
C16B C11B C10B 118.55(11) . . ?
C16B C11B C12B 119.15(11) . . ?
C11B C12B H12B 120.1 . . ?
C13B C12B C11B 119.73(12) . . ?
C13B C12B H12B 120.1 . . ?
C12B C13B H13B 119.7 . . ?
C12B C13B C14B 120.62(12) . . ?
C14B C13B H13B 119.7 . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B C13B 119.99(12) . . ?
C15B C14B H14B 120.0 . . ?
C14B C15B H15B 120.1 . . ?
C14B C15B C16B 119.77(12) . . ?
C16B C15B H15B 120.1 . . ?
C11B C16B H16B 119.7 . . ?
C15B C16B C11B 120.68(12) . . ?
C15B C16B H16B 119.7 . . ?

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
N2 N3 C10 C11 177.37(11) . . . . ?
N3 N2 C8 S1 -0.99(15) . . . . ?
N3 N2 C8 N1 179.03(11) . . . . ?
N3 C10 C11 C12 -0.9(2) . . . . ?
N3 C10 C11 C16 179.86(12) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C1 C6 C5 1.21(19) . . . . ?
C2 C1 C7 S1 73.70(13) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C6 C1 C2 C3 -0.72(19) . . . . ?
C6 C1 C7 S1 -104.67(11) . . . . ?
C7 S1 C8 N1 3.12(12) . . . . ?
C7 S1 C8 N2 -176.87(10) . . . . ?
C7 C1 C2 C3 -179.10(12) . . . . ?
C7 C1 C6 C5 179.62(12) . . . . ?
C8 S1 C7 C1 168.35(8) . . . . ?
C8 N2 N3 C10 165.69(11) . . . . ?
C9 N1 C8 S1 -171.25(10) . . . . ?
C9 N1 C8 N2 8.74(19) . . . . ?
C10 C11 C12 C13 -179.51(13) . . . . ?
C10 C11 C16 C15 178.70(13) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C15 C16 C11 1.1(2) . . . . ?
C16 C11 C12 C13 -0.2(2) . . . . ?
N2B N3B C10B C11B 175.55(10) . . . . ?
N3B N2B C8B S1B -2.17(14) . . . . ?
N3B N2B C8B N1B 176.52(10) . . . . ?
N3B C10B C11B C12B -17.98(19) . . . . ?
N3B C10B C11B C16B 165.48(12) . . . . ?
C1B C2B C3B C4B 0.53(19) . . . . ?
C2B C1B C6B C5B 1.76(18) . . . . ?
C2B C1B C7B S1B 106.47(11) . . . . ?
C2B C3B C4B C5B 0.7(2) . . . . ?
C3B C4B C5B C6B -0.7(2) . . . . ?
C4B C5B C6B C1B -0.53(19) . . . . ?
C6B C1B C2B C3B -1.75(18) . . . . ?
C6B C1B C7B S1B -74.62(12) . . . . ?
C7B S1B C8B N1B -3.28(11) . . . . ?
C7B S1B C8B N2B 175.40(10) . . . . ?
C7B C1B C2B C3B 177.18(11) . . . . ?
C7B C1B C6B C5B -177.17(11) . . . . ?
C8B S1B C7B C1B -165.71(8) . . . . ?
C8B N2B N3B C10B -168.55(11) . . . . ?
C9B N1B C8B S1B 165.88(10) . . . . ?
C9B N1B C8B N2B -12.81(18) . . . . ?
C10B C11B C12B C13B -176.50(12) . . . . ?
C10B C11B C16B C15B 178.52(12) . . . . ?
C11B C12B C13B C14B -1.8(2) . . . . ?
C12B C11B C16B C15B 1.88(19) . . . . ?
C12B C13B C14B C15B 1.8(2) . . . . ?
C13B C14B C15B C16B 0.1(2) . . . . ?
C14B C15B C16B C11B -2.0(2) . . . . ?
C16B C11B C12B C13B 0.02(19) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder'
_olex2_submission_original_sample_id RKB_230929_SDC_TL1A
_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 1.312
_oxdiff_exptl_absorpt_empirical_full_min 0.857
####################################################################### 
# 
# 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_rk_skvtl2me
_database_code_depnum_ccdc_archive 'CCDC 2506360'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Department of Chemistry, Texas A and M University, College station, Texas, United States
United States of America
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_audit_creation_date             2024-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
kar@nitt.edu
nbhuv@mail.chem.tamu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N3 O S'
_chemical_formula_sum            'C17 H17 N3 O S'
_chemical_formula_weight         311.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17  H19  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 0.0181 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                   35.0245(3)
_cell_length_b                   8.18130(10)
_cell_length_c                   10.79360(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.1190(10)
_cell_angle_gamma                90
_cell_volume                     3088.28(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19227
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      79.1950
_cell_measurement_theta_min      2.4580
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0281
-1 0 0 0.0360
-2 1 1 0.0656
0 0 -1 0.1103
0 1 0 0.0374
0 2 -1 0.0591
0 1 1 0.0782
0 -1 2 0.0726
-5 2 0 0.0425
2 -1 0 0.0566
-4 -3 0 0.0665
-5 2 -1 0.0607

_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.064
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
1.0003 -0.0000 -0.0001 -0.0087 0.0431 -0.0022
-1.0003 0.0000 0.0001 0.0087 -0.0431 0.0022
-2.0009 0.9998 0.9996 0.1213 -0.0683 -0.2070
0.0005 -0.0004 -1.0001 0.0623 0.0112 0.1282
0.0002 0.9994 -0.0007 0.1662 0.0292 -0.0833
0.0009 1.9985 -1.0015 0.3948 0.0696 -0.0384
-0.0003 0.9998 0.9994 0.1039 0.0180 -0.2114
-0.0012 -0.9987 2.0009 -0.2909 -0.0516 -0.1731
-5.0010 1.9989 -0.0009 0.3759 -0.1573 -0.1555
2.0004 -0.9995 0.0005 -0.1836 0.0571 0.0789
-4.0017 -2.9983 0.0024 -0.4639 -0.2602 0.2586
-5.0005 1.9986 -1.0010 0.4383 -0.1461 -0.0273

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32973
_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         80.135
_diffrn_reflns_theta_min         2.527
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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     49.00  74.00   0.50    0.20    --  113.25-125.00 120.00   50
  2  ω     67.00  93.00   0.50    0.20    --  113.25-125.00  90.00   52
  3  ω     64.00  89.00   0.50    0.20    --  113.25-125.00  60.00   50
  4  ω     45.00  84.00   0.50    0.20    --  113.25-125.00  30.00   78
  5  ω     44.00 106.00   0.50    0.20    --  113.25 -95.00  90.00  124
  6  ω     53.00  79.00   0.50    0.20    --  113.25 -95.00 120.00   52
  7  ω     43.00  74.00   0.50    0.20    --  113.25 -95.00 150.00   62
  8  ω     50.00  76.00   0.50    0.20    --  113.25 -95.00  60.00   52
  9  ω     43.00  69.00   0.50    0.20    --  113.25 -95.00 -60.00   52
 10  ω     45.00  94.00   0.50    0.20    --  113.25-125.00-120.00   98
 11  ω     44.00 106.00   0.50    0.20    --  113.25 -95.00-120.00  124
 12  ω     43.00  84.00   0.50    0.20    --  113.25 -88.00 -99.18   82
 13  ω     95.00 125.00   0.50    0.20    --  113.25 -88.00 -99.18   60
 14  ω     95.00 121.00   0.50    0.20    --  113.25 -88.00-172.80   52
 15  ω    -21.00  75.00   0.50    0.05    --   47.48 -87.00 -48.00  192
 16  ω    -21.00  75.00   0.50    0.05    --   47.48 -87.00 -48.00  192
 17  ω     42.00  98.00   0.50    0.20    --  113.25 -88.00  97.11  112
 18  ω     93.00 119.00   0.50    0.20    --  113.25 -84.00   3.90   52
 19  ω     42.00 141.00   0.50    0.20    --  113.25 -87.00 -48.00  198
 20  ω     86.00 132.00   0.50    0.20    --  113.25 -77.00 -60.00   92
 21  ω    111.00 136.00   0.50    0.20    --  113.25 -77.00 -30.00   50
 22  ω     65.00  91.00   0.50    0.20    --  113.25 -77.00   0.00   52
 23  ω     65.00  91.00   0.50    0.20    --  113.25 -77.00 -30.00   52
 24  ω     66.00 135.00   0.50    0.20    --  113.25 -76.00-128.31  138
 25  ω     46.00  74.00   0.50    0.20    --  113.25 -61.00 -90.00   56
 26  ω     47.00  72.00   0.50    0.20    --  113.25 -61.00 -60.00   50
 27  ω    -27.00  12.00   0.50    0.05    --   47.48 -19.00 -60.00   78
 28  ω    -27.00  12.00   0.50    0.05    --   47.48 -19.00-120.00   78
 29  ω     42.00  71.00   0.50    0.20    --  113.25 -61.00   0.00   58
 30  ω     44.00  75.00   0.50    0.20    --  113.25 -61.00  30.00   62
 31  ω     43.00  71.00   0.50    0.20    --  113.25 -61.00  90.00   56
 32  ω    115.00 141.00   0.50    0.20    --  113.25  77.00 120.00   52
 33  ω    139.00 175.00   0.50    0.20    --  113.25  77.00 150.00   72
 34  ω    148.00 177.00   0.50    0.20    --  113.25  77.00  90.00   58
 35  ω    107.00 140.00   0.50    0.20    --  113.25  61.00  30.00   66
 36  ω    115.00 160.00   0.50    0.20    --  113.25  77.00 -60.00   90
 37  ω    106.00 178.00   0.50    0.20    --  113.25  61.00   0.00  144
 38  ω    106.00 175.00   0.50    0.20    --  113.25  61.00 -90.00  138
 39  ω    107.00 144.00   0.50    0.20    --  113.25  61.00-150.00   74
 40  ω    107.00 143.00   0.50    0.20    --  113.25  61.00-180.00   72
 41  ω    119.00 160.00   0.50    0.20    --  113.25  77.00-150.00   82
 42  ω    126.00 175.00   0.50    0.20    --  113.25  77.00-180.00   98
 43  ω    144.00 170.00   0.50    0.20    --  113.25  45.00-150.00   52
 44  ω    147.00 178.00   0.50    0.20    --  113.25  30.00 -60.00   62
 45  ω    134.00 167.00   0.50    0.20    --  113.25  15.00 -90.00   66
 46  ω    102.00 137.00   0.50    0.20    --  113.25  45.00  30.00   70
 47  ω    104.00 178.00   0.50    0.20    --  113.25  45.00 150.00  148
 48  ω    103.00 163.00   0.50    0.20    --  113.25  45.00 120.00  120
 49  ω    104.00 147.00   0.50    0.20    --  113.25  30.00  60.00   86
 50  ω    125.00 150.00   0.50    0.20    --  113.25  15.00  30.00   50
 51  ω    128.00 154.00   0.50    0.20    --  113.25  15.00  90.00   52
 52  ω    145.00 176.00   0.50    0.20    --  113.25  15.00-120.00   62
 53  ω    100.00 176.00   0.50    0.20    --  113.25  15.00-120.00  152
 54  ω    101.00 134.00   0.50    0.20    --  113.25  15.00-150.00   66
 55  ω    139.00 165.00   0.50    0.20    --  113.25  15.00-180.00   52
 56  ω    106.00 131.00   0.50    0.20    --  113.25 125.00 -90.00   50
 57  ω    135.00 166.00   0.50    0.20    --  113.25 125.00 -90.00   62
 58  ω    153.00 178.00   0.50    0.20    --  113.25 125.00 120.00   50
 59  ω    152.00 177.00   0.50    0.20    --  113.25 125.00 150.00   50
 60  ω    123.00 148.00   0.50    0.20    --  113.25 125.00 150.00   50
 61  ω    102.00 139.00   0.50    0.20    --  113.25 125.00 120.00   74
 62  ω    101.00 178.00   0.50    0.20    --  113.25  87.00  68.00  154
 63  ω    110.00 158.00   0.50    0.20    --  113.25 125.00 -60.00   96
 64  ω    -12.00  28.00   0.50    0.05    --  -47.48  19.00-120.00   80
 65  ω    -39.00  26.00   0.50    0.05    --  -47.48  38.00-180.00  130
 66  ω    -39.00  26.00   0.50    0.05    --  -47.48  38.00 -90.00  130
 67  ω    -75.00  25.00   0.50    0.05    --  -47.48  87.00  68.00  200
 68  ω   -119.00 -19.00   0.50    0.20    --  -91.75  87.00  68.00  200
 69  ω   -120.00 -34.00   0.50    0.05    --  -47.48 -38.00 150.00  172
 70  ω   -163.00 -79.00   0.50    0.20    --  -91.75 -87.00 -48.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0087010000
_diffrn_orient_matrix_UB_12      0.1662707000
_diffrn_orient_matrix_UB_13      -0.0623967000
_diffrn_orient_matrix_UB_21      0.0431260000
_diffrn_orient_matrix_UB_22      0.0292037000
_diffrn_orient_matrix_UB_23      -0.0112032000
_diffrn_orient_matrix_UB_31      -0.0022172000
_diffrn_orient_matrix_UB_32      -0.0833945000
_diffrn_orient_matrix_UB_33      -0.1281245000
_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_current           '1 mA'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           '50 kV'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3175
_reflns_number_total             3365
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+3.0571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0982
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C14(H14), C6(H6), C3(H3), C15(H15), C2(H2), C17(H17),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.73638(2) 0.54108(4) 0.58856(3) 0.02234(11) Uani 1 1 d . . . . .
O1 O 0.48270(3) 0.81027(18) 0.42325(10) 0.0387(3) Uani 1 1 d . . . . .
N3 N 0.66081(3) 0.61147(14) 0.54144(10) 0.0193(2) Uani 1 1 d . . . . .
N2 N 0.67107(3) 0.40716(16) 0.67331(11) 0.0255(3) Uani 1 1 d . . . . .
N1 N 0.63181(3) 0.43112(16) 0.65565(11) 0.0256(3) Uani 1 1 d . . . . .
C8 C 0.62636(4) 0.55274(17) 0.57721(12) 0.0218(3) Uani 1 1 d . . . . .
C9 C 0.68731(4) 0.51633(17) 0.60425(12) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.81724(4) 0.50513(18) 0.78699(13) 0.0255(3) Uani 1 1 d . . . . .
H13 H 0.804010 0.579492 0.836933 0.031 Uiso 1 1 calc R U . . .
C12 C 0.79671(4) 0.39552(18) 0.71171(13) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.66906(4) 0.74903(17) 0.46116(12) 0.0226(3) Uani 1 1 d . . . . .
H10A H 0.671018 0.710082 0.375873 0.034 Uiso 1 1 calc R U . . .
H10B H 0.693286 0.799717 0.490082 0.034 Uiso 1 1 calc R U . . .
H10C H 0.648432 0.829692 0.463581 0.034 Uiso 1 1 calc R U . . .
C4 C 0.58870(4) 0.61707(17) 0.53542(12) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.58049(4) 0.67211(19) 0.41429(13) 0.0256(3) Uani 1 1 d . . . . .
H5 H 0.599638 0.666976 0.355351 0.031 Uiso 1 1 calc R U . . .
C1 C 0.51646(4) 0.7413(2) 0.46511(13) 0.0288(3) Uani 1 1 d . . . . .
C14 C 0.85689(4) 0.50766(19) 0.79035(14) 0.0278(3) Uani 1 1 d . . . . .
H14 H 0.870633 0.584387 0.841565 0.033 Uiso 1 1 calc R U . . .
C6 C 0.54479(4) 0.7339(2) 0.37950(13) 0.0297(3) Uani 1 1 d . . . . .
H6 H 0.539544 0.771419 0.297025 0.036 Uiso 1 1 calc R U . . .
C3 C 0.55960(4) 0.6195(2) 0.61899(13) 0.0279(3) Uani 1 1 d . . . . .
H3 H 0.564534 0.578831 0.700742 0.033 Uiso 1 1 calc R U . . .
C15 C 0.87639(4) 0.3986(2) 0.71921(15) 0.0314(3) Uani 1 1 d . . . . .
H15 H 0.903544 0.399419 0.721902 0.038 Uiso 1 1 calc R U . . .
C2 C 0.52363(4) 0.6804(2) 0.58435(13) 0.0303(3) Uani 1 1 d . . . . .
H2 H 0.504006 0.680439 0.641757 0.036 Uiso 1 1 calc R U . . .
C17 C 0.81654(5) 0.2870(2) 0.63964(15) 0.0341(3) Uani 1 1 d . . . . .
H17 H 0.802811 0.211700 0.587100 0.041 Uiso 1 1 calc R U . . .
C11 C 0.75373(4) 0.3951(2) 0.70680(15) 0.0314(3) Uani 1 1 d . . . . .
H11A H 0.744528 0.426317 0.788613 0.038 Uiso 1 1 calc R U . . .
H11B H 0.744002 0.284277 0.685893 0.038 Uiso 1 1 calc R U . . .
C16 C 0.85612(5) 0.2878(2) 0.64386(16) 0.0381(4) Uani 1 1 d . . . . .
H16 H 0.869419 0.212372 0.595036 0.046 Uiso 1 1 calc R U . . .
C7 C 0.45319(5) 0.8233(3) 0.50899(16) 0.0411(4) Uani 1 1 d . . . . .
H7A H 0.430900 0.877804 0.468660 0.062 Uiso 1 1 calc R U . . .
H7B H 0.462518 0.887346 0.581180 0.062 Uiso 1 1 calc R U . . .
H7C H 0.445898 0.713851 0.535944 0.062 Uiso 1 1 calc R U . . .


_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 1.7478(14) . ?
S1 C11 1.8278(15) . ?
O1 C1 1.3644(18) . ?
O1 C7 1.4285(19) . ?
N3 C8 1.3733(17) . ?
N3 C9 1.3634(18) . ?
N3 C10 1.4589(17) . ?
N2 N1 1.3920(17) . ?
N2 C9 1.3126(18) . ?
N1 C8 1.3136(18) . ?
C8 C4 1.4684(19) . ?
C13 H13 0.9500 . ?
C13 C12 1.385(2) . ?
C13 C14 1.387(2) . ?
C12 C17 1.391(2) . ?
C12 C11 1.503(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 C5 1.3978(19) . ?
C4 C3 1.3972(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.390(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(2) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C2 H2 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.385(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C16 H16 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C9 S1 C11 98.51(7) . . ?
C1 O1 C7 117.45(12) . . ?
C8 N3 C10 129.97(12) . . ?
C9 N3 C8 104.20(11) . . ?
C9 N3 C10 125.74(11) . . ?
C9 N2 N1 106.37(11) . . ?
C8 N1 N2 107.61(11) . . ?
N3 C8 C4 125.21(12) . . ?
N1 C8 N3 110.32(12) . . ?
N1 C8 C4 124.46(12) . . ?
N3 C9 S1 122.15(10) . . ?
N2 C9 S1 126.34(11) . . ?
N2 C9 N3 111.50(12) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.79(14) . . ?
C14 C13 H13 119.6 . . ?
C13 C12 C17 118.86(14) . . ?
C13 C12 C11 120.61(14) . . ?
C17 C12 C11 120.53(14) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 C8 122.57(12) . . ?
C3 C4 C8 118.78(12) . . ?
C3 C4 C5 118.64(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.60(13) . . ?
C6 C5 H5 119.7 . . ?
O1 C1 C6 115.71(13) . . ?
O1 C1 C2 124.36(13) . . ?
C2 C1 C6 119.93(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.01(14) . . ?
C15 C14 H14 120.0 . . ?
C5 C6 C1 120.15(13) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.98(13) . . ?
C2 C3 H3 119.5 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.67(14) . . ?
C16 C15 H15 120.2 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.60(13) . . ?
C3 C2 H2 120.2 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.52(15) . . ?
C16 C17 H17 119.7 . . ?
S1 C11 H11A 110.0 . . ?
S1 C11 H11B 110.0 . . ?
C12 C11 S1 108.49(10) . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.14(15) . . ?
C17 C16 H16 119.9 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
O1 C1 C6 C5 177.48(15) . . . . ?
O1 C1 C2 C3 -177.07(15) . . . . ?
N3 C8 C4 C5 37.4(2) . . . . ?
N3 C8 C4 C3 -144.31(14) . . . . ?
N2 N1 C8 N3 0.01(15) . . . . ?
N2 N1 C8 C4 -179.33(12) . . . . ?
N1 N2 C9 S1 -179.10(10) . . . . ?
N1 N2 C9 N3 -0.09(16) . . . . ?
N1 C8 C4 C5 -143.35(15) . . . . ?
N1 C8 C4 C3 34.9(2) . . . . ?
C8 N3 C9 S1 179.15(10) . . . . ?
C8 N3 C9 N2 0.10(15) . . . . ?
C8 C4 C5 C6 -179.06(14) . . . . ?
C8 C4 C3 C2 179.42(14) . . . . ?
C9 S1 C11 C12 -179.50(11) . . . . ?
C9 N3 C8 N1 -0.07(15) . . . . ?
C9 N3 C8 C4 179.27(13) . . . . ?
C9 N2 N1 C8 0.05(16) . . . . ?
C13 C12 C17 C16 0.5(2) . . . . ?
C13 C12 C11 S1 87.70(15) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C12 C17 C16 C15 -0.7(3) . . . . ?
C10 N3 C8 N1 -176.79(12) . . . . ?
C10 N3 C8 C4 2.6(2) . . . . ?
C10 N3 C9 S1 -3.95(18) . . . . ?
C10 N3 C9 N2 177.00(12) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C3 C2 C1 -0.6(2) . . . . ?
C5 C4 C3 C2 -2.2(2) . . . . ?
C14 C13 C12 C17 0.3(2) . . . . ?
C14 C13 C12 C11 -179.00(13) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C6 C1 C2 C3 3.0(3) . . . . ?
C3 C4 C5 C6 2.6(2) . . . . ?
C2 C1 C6 C5 -2.6(3) . . . . ?
C17 C12 C11 S1 -91.59(15) . . . . ?
C11 S1 C9 N3 174.28(12) . . . . ?
C11 S1 C9 N2 -6.81(14) . . . . ?
C11 C12 C17 C16 179.78(14) . . . . ?
C7 O1 C1 C6 -178.71(16) . . . . ?
C7 O1 C1 C2 1.4(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder'
_olex2_submission_original_sample_id RKB_241022_Sc_SKVTL2Me
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_rk_tl5a
_database_code_depnum_ccdc_archive 'CCDC 2506361'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Department of Chemistry, Texas A and M University, College station, Texas, United States
United States of America
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_audit_creation_date             2024-03-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
kar@nitt.edu
nbhuv@mail.chem.tamu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N4 O2 S'
_chemical_formula_sum            'C16 H14 N4 O2 S'
_chemical_formula_weight         326.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   18.0524(4)
_cell_length_b                   7.4997(2)
_cell_length_c                   11.6915(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.138(2)
_cell_angle_gamma                90
_cell_volume                     1520.51(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8546
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6230
_cell_measurement_theta_min      2.5320
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    2.030
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023) 
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -2 0.0279
-1 0 2 0.0267
1 -2 1 0.0589
0 1 -1 0.0604
-1 0 0 0.0095
1 0 0 0.0069

_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.016
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
1.0040 -0.0002 -1.9997 -0.0637 0.1894 -0.1723
-1.0040 0.0002 1.9997 0.0637 -0.1894 0.1723
0.9946 -1.9989 1.0004 -0.0791 0.1702 0.4085
0.0038 0.9994 -1.0000 0.0019 -0.0402 -0.2436
-1.0004 0.0002 -0.0006 0.0871 0.0098 -0.0149
1.0004 -0.0002 0.0006 -0.0871 -0.0098 0.0149

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15216
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.492
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -30.00   0.50    0.50    --  -46.64 -57.00-164.00  178
  2  ω    -63.00  26.00   0.50    0.50    --  -46.64  57.00 -23.00  178
  3  ω    -25.00  63.00   0.50    0.50    --   46.64 -57.00-164.00  176
  4  ω    -67.00 -19.00   0.50    2.00    --  -91.75  57.00 -23.00   96
  5  ω   -164.00 -75.00   0.50    2.00    --  -91.75 -57.00-164.00  178
  6  ω     97.00 178.00   0.50    2.00    --  113.25  57.00 -23.00  162
  7  ω     41.00  68.00   0.50    2.00    --  113.25 -57.00-164.00   54
  8  ω    -13.00  29.00   0.50    0.50    --  -46.64  19.00 150.00   84
  9  ω    -13.00  29.00   0.50    0.50    --  -46.64  19.00 120.00   84
 10  ω    -29.00  12.00   0.50    0.50    --   46.64 -19.00-150.00   82
 11  ω    -49.00 -19.00   0.50    2.00    --  -91.75  45.00 150.00   60
 12  ω    -49.00 -19.00   0.50    2.00    --  -91.75  45.00-180.00   60
 13  ω    110.00 178.00   0.50    2.00    --  113.25  77.00  30.00  136
 14  ω     95.00 178.00   0.50    2.00    --  113.25 125.00 -90.00  166
 15  ω     41.00  75.00   0.50    2.00    --  113.25 -61.00  90.00   68
 16  ω     41.00  75.00   0.50    2.00    --  113.25 -61.00-120.00   68
 17  ω     96.00 176.00   0.50    2.00    --  113.25  15.00 120.00  160
 18  ω     41.00  75.00   0.50    2.00    --  113.25 -61.00 120.00   68
 19  ω     41.00  75.00   0.50    2.00    --  113.25 -61.00-180.00   68
 20  ω     96.00 176.00   0.50    2.00    --  113.25  15.00 150.00  160
 21  ω     96.00 176.00   0.50    2.00    --  113.25  15.00 150.00  160
 22  ω     41.00 106.00   0.50    2.00    --  113.25 -95.00 -60.00  130
 23  ω     95.00 178.00   0.50    2.00    --  113.25 125.00   0.00  166
 24  ω     95.00 178.00   0.50    2.00    --  113.25 125.00-150.00  166
 25  ω     99.00 124.00   0.50    2.00    --  113.25 125.00-150.00   50
 26  ω     48.00  75.00   0.50    2.00    --  113.25 -77.00 -60.00   54
 27  ω    110.00 137.00   0.50    2.00    --  113.25 -77.00 -60.00   54
 28  ω     43.00  72.00   0.50    2.00    --  113.25 -61.00   0.00   58
 29  ω    151.00 176.00   0.50    2.00    --  113.25  77.00  30.00   50
 30  ω     41.00  74.00   0.50    2.00    --  113.25 -61.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0870622000
_diffrn_orient_matrix_UB_12      -0.0096711000
_diffrn_orient_matrix_UB_13      -0.0118562000
_diffrn_orient_matrix_UB_21      -0.0097235000
_diffrn_orient_matrix_UB_22      -0.1398325000
_diffrn_orient_matrix_UB_23      -0.0995645000
_diffrn_orient_matrix_UB_31      0.0147664000
_diffrn_orient_matrix_UB_32      -0.1501806000
_diffrn_orient_matrix_UB_33      0.0935748000
_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_current           '1 mA'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           '50 kV'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2828
_reflns_number_total             3116
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.103a 64-bit (release 20-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.398
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.050
_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)+(0.0979P)²+1.3456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1592
_refine_special_details          
;
Crystal quality was bad. Several crystals were tried before 
the best among them was chosen for collecting full data. 

Highest residual electron density peak of 1.4 electrons per cubic 
angstrom was present close to S1. Our efforts to modify 
the absorption correction parameters did not improve the 
results. 
;
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 0.76410(3) 0.59401(7) 0.40232(5) 0.0300(2) Uani 1 1 d . . . . .
O1 O 0.18565(12) 0.5907(3) 0.0579(2) 0.0592(6) Uani 1 1 d . . . . .
O2 O 0.22713(12) 0.6921(3) -0.08598(19) 0.0564(6) Uani 1 1 d . . . . .
N1 N 0.63851(11) 0.6657(3) 0.48387(16) 0.0304(4) Uani 1 1 d . . . . .
N2 N 0.55908(11) 0.6711(3) 0.43617(16) 0.0285(4) Uani 1 1 d . . . . .
N3 N 0.61001(10) 0.5975(2) 0.29196(16) 0.0238(4) Uani 1 1 d . . . . .
N4 N 0.23699(12) 0.6387(3) 0.0173(2) 0.0432(5) Uani 1 1 d . . . . .
C1 C 0.66721(12) 0.6218(3) 0.39673(19) 0.0263(4) Uani 1 1 d . . . . .
C2 C 0.54343(12) 0.6299(3) 0.32264(18) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.62020(13) 0.5306(3) 0.18035(18) 0.0280(5) Uani 1 1 d . . . . .
H3A H 0.572401 0.473554 0.134130 0.042 Uiso 1 1 calc R U . . .
H3B H 0.662247 0.443332 0.197218 0.042 Uiso 1 1 calc R U . . .
H3C H 0.632793 0.629956 0.134611 0.042 Uiso 1 1 calc R U . . .
C4 C 0.46530(12) 0.6257(3) 0.24080(18) 0.0229(4) Uani 1 1 d . . . . .
C5 C 0.40516(13) 0.5547(3) 0.2811(2) 0.0274(4) Uani 1 1 d . . . . .
H5 H 0.415928 0.503918 0.358427 0.033 Uiso 1 1 calc R U . . .
C6 C 0.33022(13) 0.5584(3) 0.2085(2) 0.0317(5) Uani 1 1 d . . . . .
H6 H 0.289224 0.510122 0.235004 0.038 Uiso 1 1 calc R U . . .
C7 C 0.31610(13) 0.6337(3) 0.0964(2) 0.0314(5) Uani 1 1 d . . . . .
C8 C 0.37447(13) 0.7045(3) 0.05427(19) 0.0281(4) Uani 1 1 d . . . . .
H8 H 0.363169 0.755748 -0.022982 0.034 Uiso 1 1 calc R U . . .
C9 C 0.44926(12) 0.6992(3) 0.12654(18) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.490008 0.745656 0.098607 0.030 Uiso 1 1 calc R U . . .
C10 C 0.80690(14) 0.6552(3) 0.5581(2) 0.0336(5) Uani 1 1 d . . . . .
H10A H 0.789577 0.776088 0.572922 0.040 Uiso 1 1 calc R U . . .
H10B H 0.789931 0.570331 0.610547 0.040 Uiso 1 1 calc R U . . .
C11 C 0.89378(13) 0.6517(3) 0.5857(2) 0.0309(5) Uani 1 1 d . . . . .
C12 C 0.93235(14) 0.7443(3) 0.5158(2) 0.0332(5) Uani 1 1 d . . . . .
H12 H 0.903757 0.808578 0.447855 0.040 Uiso 1 1 calc R U . . .
C13 C 1.01201(14) 0.7427(3) 0.5453(2) 0.0358(5) Uani 1 1 d . . . . .
H13 H 1.038113 0.804832 0.497227 0.043 Uiso 1 1 calc R U . . .
C14 C 1.05373(14) 0.6503(4) 0.6453(2) 0.0391(6) Uani 1 1 d . . . . .
H14 H 1.108481 0.649959 0.665906 0.047 Uiso 1 1 calc R U . . .
C15 C 1.01599(17) 0.5591(4) 0.7146(2) 0.0433(6) Uani 1 1 d . . . . .
H15 H 1.044735 0.496317 0.783224 0.052 Uiso 1 1 calc R U . . .
C16 C 0.93627(16) 0.5588(3) 0.6845(2) 0.0383(5) Uani 1 1 d . . . . .
H16 H 0.910487 0.494305 0.732030 0.046 Uiso 1 1 calc R U . . .


_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 C1 1.745(2) . ?
S1 C10 1.828(2) . ?
O1 N4 1.208(3) . ?
O2 N4 1.237(3) . ?
N1 N2 1.387(3) . ?
N1 C1 1.307(3) . ?
N2 C2 1.315(3) . ?
N3 C1 1.377(3) . ?
N3 C2 1.368(3) . ?
N3 C3 1.456(3) . ?
N4 C7 1.470(3) . ?
C2 C4 1.468(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.403(3) . ?
C4 C9 1.399(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(4) . ?
C7 C8 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.511(3) . ?
C11 C12 1.396(3) . ?
C11 C16 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(4) . ?
C16 H16 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
C1 S1 C10 98.58(10) . . ?
C1 N1 N2 106.46(18) . . ?
C2 N2 N1 107.89(17) . . ?
C1 N3 C3 126.32(18) . . ?
C2 N3 C1 103.85(18) . . ?
C2 N3 C3 129.41(19) . . ?
O1 N4 O2 124.2(2) . . ?
O1 N4 C7 117.6(3) . . ?
O2 N4 C7 118.2(2) . . ?
N1 C1 S1 127.69(17) . . ?
N1 C1 N3 111.41(19) . . ?
N3 C1 S1 120.90(16) . . ?
N2 C2 N3 110.39(19) . . ?
N2 C2 C4 124.13(18) . . ?
N3 C2 C4 125.45(18) . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 118.82(19) . . ?
C9 C4 C2 121.35(18) . . ?
C9 C4 C5 119.7(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.7(2) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 N4 119.8(2) . . ?
C6 C7 C8 122.3(2) . . ?
C8 C7 N4 117.9(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.24(19) . . ?
C8 C9 H9 119.9 . . ?
S1 C10 H10A 109.8 . . ?
S1 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 S1 109.57(16) . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C12 C11 C10 121.5(2) . . ?
C16 C11 C10 119.2(2) . . ?
C16 C11 C12 119.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?

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 C10 C11 C12 52.3(3) . . . . ?
S1 C10 C11 C16 -129.6(2) . . . . ?
O1 N4 C7 C6 6.7(3) . . . . ?
O1 N4 C7 C8 -173.9(2) . . . . ?
O2 N4 C7 C6 -173.6(2) . . . . ?
O2 N4 C7 C8 5.8(3) . . . . ?
N1 N2 C2 N3 -0.3(2) . . . . ?
N1 N2 C2 C4 -178.41(18) . . . . ?
N2 N1 C1 S1 179.99(16) . . . . ?
N2 N1 C1 N3 0.0(2) . . . . ?
N2 C2 C4 C5 -40.6(3) . . . . ?
N2 C2 C4 C9 136.0(2) . . . . ?
N3 C2 C4 C5 141.6(2) . . . . ?
N3 C2 C4 C9 -41.8(3) . . . . ?
N4 C7 C8 C9 -179.21(19) . . . . ?
C1 S1 C10 C11 -176.95(17) . . . . ?
C1 N1 N2 C2 0.2(2) . . . . ?
C1 N3 C2 N2 0.3(2) . . . . ?
C1 N3 C2 C4 178.39(19) . . . . ?
C2 N3 C1 S1 179.84(15) . . . . ?
C2 N3 C1 N1 -0.2(2) . . . . ?
C2 C4 C5 C6 176.23(19) . . . . ?
C2 C4 C9 C8 -175.57(18) . . . . ?
C3 N3 C1 S1 6.7(3) . . . . ?
C3 N3 C1 N1 -173.30(19) . . . . ?
C3 N3 C2 N2 173.10(19) . . . . ?
C3 N3 C2 C4 -8.8(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C4 C9 C8 1.0(3) . . . . ?
C5 C6 C7 N4 179.75(19) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C4 -0.9(3) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
C10 S1 C1 N1 -2.7(2) . . . . ?
C10 S1 C1 N3 177.23(17) . . . . ?
C10 C11 C12 C13 178.2(2) . . . . ?
C10 C11 C16 C15 -177.5(2) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C11 -0.9(4) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder'
_olex2_submission_original_sample_id RKB_240321_SDc_TL5A
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.768
####################################################################### 
# 
# 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_rk_skvtl5
_database_code_depnum_ccdc_archive 'CCDC 2506370'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Department of Chemistry, Texas A and M University, College station, Texas, United States
United States of America
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
kar@nitt.edu
nbhuv@mail.chem.tamu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C16 H17 N4 O2 S, H2 O'
_chemical_formula_sum            'C16 H19 Br N4 O3 S'
_chemical_formula_weight         427.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOS
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'
Br Br -0.6763 1.2805 '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                   6.81290(10)
_cell_length_b                   9.15510(10)
_cell_length_c                   15.64500(10)
_cell_angle_alpha                83.8980(10)
_cell_angle_beta                 78.1950(10)
_cell_angle_gamma                71.0320(10)
_cell_volume                     902.482(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    27598
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4190
_cell_measurement_theta_min      5.1130
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.441
_exptl_absorpt_coefficient_mu    4.393
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023) 
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0438
0 -1 0 0.0476
2 1 1 0.0948
-2 -2 -1 0.1103
0 0 1 0.0256
0 0 -1 0.0282
-1 0 -2 0.0879

_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.054
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
-0.0014 0.9989 0.0003 -0.0148 0.1658 0.0631
0.0014 -0.9989 -0.0003 0.0148 -0.1658 -0.0631
1.9970 1.0045 1.0138 0.0192 -0.1379 0.4303
-1.9956 -2.0034 -1.0141 -0.0043 -0.0279 -0.4933
-0.0011 -0.0016 0.9984 -0.0996 -0.0142 0.0012
0.0011 0.0016 -0.9984 0.0996 0.0142 -0.0012
-0.9976 -0.0005 -2.0043 0.1324 0.1731 -0.1854

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31293
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.501
_diffrn_reflns_theta_min         5.113
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  28.00   0.50    0.10    --   18.00  65.00 159.76   56
  2  ω     -6.00  22.00   0.50    0.10    --   14.00  70.00  75.77   56
  3  ω      5.00  31.00   0.50    0.10    --   22.00  62.00 -11.22   52
  4  ω     35.00 119.00   0.50    0.10    --   47.91  47.00  21.07  168
  5  ω     35.00 119.00   0.50    0.10    --   47.91  47.00-164.40  168
  6  ω     42.00  67.00   0.50    0.40    --  113.25 -61.00   0.00   50
  7  ω     43.00  73.00   0.50    0.40    --  113.25 -61.00 -60.00   60
  8  ω     42.00  68.00   0.50    0.40    --  113.25 -61.00 -30.00   52
  9  ω     43.00  74.00   0.50    0.40    --  113.25 -61.00 120.00   62
 10  ω     41.00 102.00   0.50    0.10    --   47.91-137.00 156.00  122
 11  ω     42.00 121.00   0.50    0.40    --  113.25-137.00 156.00  158
 12  ω     42.00 121.00   0.50    0.40    --  113.25-137.00 156.00  158
 13  ω     39.00  99.00   0.50    0.10    --   47.91-133.00 -25.00  120
 14  ω     82.00 107.00   0.50    0.40    --  113.25-125.00-150.00   50
 15  ω     50.00  76.00   0.50    0.40    --  113.25-125.00-150.00   52
 16  ω     49.00  75.00   0.50    0.40    --  113.25-125.00 -90.00   52
 17  ω     45.00  75.00   0.50    0.40    --  113.25-125.00 -60.00   60
 18  ω     43.00 117.00   0.50    0.40    --  113.25-133.00 -25.00  148
 19  ω     79.00 106.00   0.50    0.40    --  113.25-125.00  90.00   54
 20  ω     83.00 110.00   0.50    0.40    --  113.25-125.00 120.00   54
 21  ω     44.00  69.00   0.50    0.40    --  113.25-125.00 120.00   50
 22  ω     43.00  69.00   0.50    0.40    --  113.25 -95.00 150.00   52
 23  ω     73.00  99.00   0.50    0.40    --  113.25 -95.00 150.00   52
 24  ω     45.00  73.00   0.50    0.40    --  113.25-125.00  90.00   56
 25  ω     46.00  72.00   0.50    0.40    --  113.25 -95.00  90.00   52
 26  ω     78.00 105.00   0.50    0.40    --  113.25 -95.00  90.00   54
 27  ω     78.00 104.00   0.50    0.40    --  113.25 -95.00 120.00   52
 28  ω     75.00 106.00   0.50    0.40    --  113.25 -95.00 -60.00   62
 29  ω     49.00  89.00   0.50    0.40    --  110.00 -88.00-106.00   80
 30  ω     56.00 106.00   0.50    0.40    --  113.25 -95.00-150.00  100
 31  ω    102.00 133.00   0.50    0.40    --  110.00 -88.00-106.00   62
 32  ω    103.00 159.00   0.50    0.40    --  113.25  45.00-180.00  112
 33  ω    112.00 175.00   0.50    0.40    --  113.25  77.00 -30.00  126
 34  ω    139.00 177.00   0.50    0.40    --  113.25  61.00   0.00   76
 35  ω    106.00 133.00   0.50    0.40    --  113.25  61.00   0.00   54
 36  ω    110.00 140.00   0.50    0.40    --  113.25  77.00  60.00   60
 37  ω    141.00 167.00   0.50    0.40    --  113.25  61.00 150.00   52
 38  ω    106.00 134.00   0.50    0.40    --  113.25  61.00 150.00   56
 39  ω    108.00 178.00   0.50    0.40    --  113.25  61.00  90.00  140
 40  ω    153.00 178.00   0.50    0.40    --  113.25  61.00  60.00   50
 41  ω    152.00 178.00   0.50    0.40    --  113.25  45.00  30.00   52
 42  ω    106.00 140.00   0.50    0.40    --  113.25  61.00  60.00   68
 43  ω    150.00 177.00   0.50    0.40    --  113.25  45.00 120.00   54
 44  ω    101.00 130.00   0.50    0.40    --  113.25  45.00  30.00   58
 45  ω    103.00 140.00   0.50    0.40    --  113.25  45.00 120.00   74
 46  ω    109.00 155.00   0.50    0.40    --  113.25  61.00 -60.00   92
 47  ω    101.00 127.00   0.50    0.40    --  113.25  45.00-120.00   52
 48  ω    103.00 167.00   0.50    0.40    --  113.25  45.00-150.00  128
 49  ω    152.00 178.00   0.50    0.40    --  113.25  45.00 -90.00   52
 50  ω    106.00 176.00   0.50    0.40    --  113.25  61.00-120.00  140
 51  ω    101.00 131.00   0.50    0.40    --  113.25  45.00 -30.00   60
 52  ω    144.00 170.00   0.50    0.40    --  113.25  45.00 -30.00   52
 53  ω    103.00 131.00   0.50    0.40    --  113.25  45.00 -90.00   56
 54  ω    101.00 129.00   0.50    0.40    --  113.25  45.00 -60.00   56
 55  ω    101.00 150.00   0.50    0.40    --  113.25  45.00   0.00   98
 56  ω    101.00 127.00   0.50    0.40    --  113.25  45.00  60.00   52
 57  ω    102.00 147.00   0.50    0.40    --  113.25  45.00 150.00   90
 58  ω    118.00 158.00   0.50    0.40    --  113.25 125.00  60.00   80
 59  ω    116.00 170.00   0.50    0.40    --  113.25 125.00 150.00  108
 60  ω     90.00 178.00   0.50    0.40    --  113.25 133.00  41.00  176
 61  ω     87.00 178.00   0.50    0.40    --  113.25 137.00-140.00  182
 62  ω    -42.00 -15.00   0.50    0.10    --  -30.00 -55.00  73.01   54
 63  ω    -48.00 -20.00   0.50    0.10    --  -34.00 -52.00 137.01   56
 64  ω    -54.00 -28.00   0.50    0.10    --  -42.00 -50.00 115.87   52
 65  ω    -61.00 -28.00   0.50    0.10    --  -42.00 -48.00  29.99   66
 66  ω   -117.00 -33.00   0.50    0.10    --  -46.00 -47.00  20.04  168
 67  ω   -119.00 -35.00   0.50    0.10    --  -47.91 -46.00 -69.50  168
 68  ω    -54.00 -28.00   0.50    0.10    --  -42.00 -50.00-131.13   52
 69  ω    -54.00 -28.00   0.50    0.10    --  -42.00 -50.00-168.96   52
 70  ω   -119.00 -35.00   0.50    0.10    --  -47.91 -45.00-142.66  168
 71  ω   -119.00 -35.00   0.50    0.10    --  -47.91 -45.00-142.66  168
 72  ω   -122.00 -37.00   0.50    0.10    --  -50.00 -45.00  59.93  170
 73  ω   -122.00 -37.00   0.50    0.10    --  -50.00 -45.00  59.93  170
 74  ω   -118.00 -68.00   0.50    0.10    --  -47.91-133.00 -25.00  100
 75  ω   -161.00 -68.00   0.50    0.40    --  -91.75-133.00 -25.00  186
 76  ω   -119.00 -66.00   0.50    0.10    --  -47.91-137.00 156.00  106
 77  ω   -158.00 -66.00   0.50    0.40    --  -91.75-137.00 156.00  184
 78  ω   -104.00 -78.00   0.50    0.40    --  -91.75 -39.00 111.39   52
 79  ω   -134.00 -49.00   0.50    0.10    --  -62.00 -47.00 168.40  170
 80  ω   -134.00 -49.00   0.50    0.10    --  -62.00 -47.00 -73.60  170
 81  ω   -134.00 -49.00   0.50    0.10    --  -62.00 -47.00 -73.60  170
 82  ω   -134.00 -49.00   0.50    0.10    --  -62.00 -47.00 -26.13  170
 83  ω   -134.00 -49.00   0.50    0.10    --  -62.00 -47.00 -26.13  170
 84  ω    -91.00 -57.00   0.50    0.10    --  -70.00 -47.00-129.76   68
 85  ω   -111.00 -83.00   0.50    0.40    --  -91.75 -47.00-100.50   56
 86  ω    -90.00 -57.00   0.50    0.10    --  -70.00 -47.00  28.36   66
 87  ω   -109.00 -83.00   0.50    0.40    --  -91.75 -47.00   9.14   52
 88  ω   -112.00 -81.00   0.50    0.40    --  -91.75 -47.00 111.11   62
 89  ω   -108.00 -82.00   0.50    0.40    --  -91.75 -47.00 158.51   52
 90  ω   -138.00 -53.00   0.50    0.10    --  -66.00 -47.00 122.74  170
 91  ω   -137.00-110.00   0.50    0.10    --  -66.00 -47.00 122.74   54
 92  ω   -162.00-124.00   0.50    0.40    --  -91.75 -45.00  90.00   76
 93  ω    -96.00 -57.00   0.50    0.10    --  -70.00 -45.00  38.95   78
 94  ω   -108.00 -81.00   0.50    0.40    --  -91.75 -46.00 -10.74   54
 95  ω   -116.00 -79.00   0.50    0.40    --  -91.75 -45.00  90.00   74
 96  ω    -83.00 -57.00   0.50    0.10    --  -70.00 -45.00  71.83   52
 97  ω   -105.00 -79.00   0.50    0.40    --  -91.75 -45.00  60.00   52
 98  ω   -105.00 -79.00   0.50    0.40    --  -91.75 -45.00  30.00   52
 99  ω   -113.00 -80.00   0.50    0.40    --  -91.75 -45.00 -60.00   66
100  ω   -144.00-118.00   0.50    0.40    --  -91.75 -45.00-120.00   52
101  ω   -104.00 -79.00   0.50    0.40    --  -91.75 -45.00-150.00   50
102  ω   -106.00 -80.00   0.50    0.40    --  -91.75 -46.00-167.63   52
103  ω   -163.00-125.00   0.50    0.40    --  -91.75 -45.00-150.00   76
104  ω   -161.00-118.00   0.50    0.40    --  -91.75 -45.00 -90.00   86
105  ω   -108.00 -81.00   0.50    0.40    --  -91.75 -45.00-120.00   54
106  ω   -106.00 -80.00   0.50    0.40    --  -91.75 -45.00 -90.00   52
107  ω    -98.00 -72.00   0.50    0.40    --  -86.00 -44.00 -89.07   52
108  ω   -130.00 -44.00   0.50    0.10    --  -58.00 -44.00-170.40  172
109  ω   -126.00 -41.00   0.50    0.10    --  -54.00 -44.00  12.54  170
110  ω   -126.00 -41.00   0.50    0.10    --  -54.00 -44.00  12.54  170
111  ω    -89.00 -57.00   0.50    0.10    --  -70.00 -45.00  52.12   64
112  ω    -80.00 -54.00   0.50    0.10    --  -66.00 -44.00 136.82   52
113  ω    -94.00 -68.00   0.50    0.40    --  -82.00 -43.00 131.63   52
114  ω   -110.00 -78.00   0.50    0.40    --  -90.00 -42.00 169.05   64
115  ω   -146.00-120.00   0.50    0.40    --  -82.00 -43.00 131.63   52
116  ω    -85.00 -59.00   0.50    0.10    --  -70.00 -41.00 178.45   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0676201000
_diffrn_orient_matrix_UB_12      -0.0147320000
_diffrn_orient_matrix_UB_13      -0.0996913000
_diffrn_orient_matrix_UB_21      -0.1453106000
_diffrn_orient_matrix_UB_22      0.1657733000
_diffrn_orient_matrix_UB_23      -0.0140737000
_diffrn_orient_matrix_UB_31      0.1828027000
_diffrn_orient_matrix_UB_32      0.0634157000
_diffrn_orient_matrix_UB_33      0.0014749000
_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_current           '1 mA'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           '50 kV'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3692
_reflns_number_total             3698
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.103a 64-bit (release 20-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.067
_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)+(0.0301P)²+0.5131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0597
_refine_special_details          
;
Hydrogen atoms on O1w, N1 and N2 were located from the 
difference Fourier maps and were the set riding on the 
parent atom at idealized distances. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2), O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
Br1 Br 0.24004(2) 0.86482(2) 0.36382(2) 0.02238(7) Uani 1 1 d . . . . .
S1 S 0.33099(5) 0.74370(4) 0.80179(2) 0.01769(9) Uani 1 1 d . . . . .
O1 O 1.17803(19) 0.40023(13) 0.12485(7) 0.0267(2) Uani 1 1 d . . . . .
O2 O 1.20273(18) 0.18387(12) 0.19967(8) 0.0269(2) Uani 1 1 d . . . . .
N1 N 0.53665(19) 0.48398(14) 0.72476(8) 0.0182(2) Uani 1 1 d . . . . .
H1 H 0.604587 0.426749 0.679637 0.022 Uiso 1 1 calc R U . . .
N2 N 0.50609(19) 0.70000(14) 0.63161(8) 0.0174(2) Uani 1 1 d . . . . .
H2 H 0.425758 0.795974 0.618309 0.021 Uiso 1 1 d R U . . .
N3 N 0.62252(19) 0.59877(14) 0.56596(8) 0.0179(2) Uani 1 1 d . . . . .
N4 N 1.1436(2) 0.32570(14) 0.19323(8) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.2781(3) 0.94386(16) 0.75982(10) 0.0220(3) Uani 1 1 d . . . . .
H1A H 0.409337 0.961911 0.727058 0.026 Uiso 1 1 calc R U . . .
H1B H 0.173691 0.969008 0.720484 0.026 Uiso 1 1 calc R U . . .
C2 C 0.1918(2) 1.04106(16) 0.83932(9) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.3290(2) 1.07651(17) 0.88267(10) 0.0223(3) Uani 1 1 d . . . . .
H3 H 0.477094 1.037974 0.862954 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2482(3) 1.16869(18) 0.95508(10) 0.0244(3) Uani 1 1 d . . . . .
H4 H 0.341265 1.193855 0.984418 0.029 Uiso 1 1 calc R U . . .
C5 C 0.0318(3) 1.22367(17) 0.98427(10) 0.0234(3) Uani 1 1 d . . . . .
H5 H -0.023092 1.287944 1.032976 0.028 Uiso 1 1 calc R U . . .
C6 C -0.1044(3) 1.18518(17) 0.94265(10) 0.0225(3) Uani 1 1 d . . . . .
H6 H -0.252144 1.221116 0.963704 0.027 Uiso 1 1 calc R U . . .
C7 C -0.0251(2) 1.09378(17) 0.86991(10) 0.0213(3) Uani 1 1 d . . . . .
H7 H -0.118572 1.067562 0.841319 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4668(2) 0.63455(16) 0.71109(9) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.5078(3) 0.40649(17) 0.81050(10) 0.0226(3) Uani 1 1 d . . . . .
H9A H 0.567232 0.294355 0.804778 0.034 Uiso 1 1 calc R U . . .
H9B H 0.356867 0.433187 0.835168 0.034 Uiso 1 1 calc R U . . .
H9C H 0.579914 0.439801 0.849253 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6692(2) 0.66461(17) 0.49185(10) 0.0182(3) Uani 1 1 d . . . . .
H10 H 0.622310 0.774194 0.485210 0.022 Uiso 1 1 calc R U . . .
C11 C 0.7947(2) 0.57213(16) 0.41705(9) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.8365(2) 0.65129(16) 0.33756(10) 0.0195(3) Uani 1 1 d . . . . .
H12 H 0.785210 0.761037 0.334048 0.023 Uiso 1 1 calc R U . . .
C13 C 0.9522(2) 0.57144(17) 0.26369(10) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.980817 0.624543 0.209377 0.024 Uiso 1 1 calc R U . . .
C14 C 1.0248(2) 0.41088(16) 0.27190(9) 0.0175(3) Uani 1 1 d . . . . .
C15 C 0.9893(2) 0.32854(16) 0.35013(10) 0.0186(3) Uani 1 1 d . . . . .
H15 H 1.043671 0.218902 0.353497 0.022 Uiso 1 1 calc R U . . .
C16 C 0.8728(2) 0.41002(16) 0.42317(10) 0.0181(3) Uani 1 1 d . . . . .
H16 H 0.845593 0.356265 0.477404 0.022 Uiso 1 1 calc R U . . .
O1W O 0.26508(17) 0.97402(12) 0.55443(7) 0.0230(2) Uani 1 1 d . . . . .
H1WA H 0.256182 0.963359 0.502186 0.028 Uiso 1 1 d R U . . .
H1WB H 0.133262 1.013519 0.572156 0.028 Uiso 1 1 d R U . . .


_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 C1 1.8250(15) . ?
S1 C8 1.7411(14) . ?
O1 N4 1.2294(17) . ?
O2 N4 1.2277(17) . ?
N1 H1 0.8800 . ?
N1 C8 1.3134(19) . ?
N1 C9 1.4566(19) . ?
N2 H2 0.9000 . ?
N2 N3 1.3907(16) . ?
N2 C8 1.3366(19) . ?
N3 C10 1.278(2) . ?
N4 C14 1.4711(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5101(19) . ?
C2 C3 1.394(2) . ?
C2 C7 1.393(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(2) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.4656(19) . ?
C11 C12 1.397(2) . ?
C11 C16 1.404(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(2) . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8500 . ?

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 C1 104.42(7) . . ?
C8 N1 H1 118.2 . . ?
C8 N1 C9 123.61(12) . . ?
C9 N1 H1 118.2 . . ?
N3 N2 H2 120.6 . . ?
C8 N2 H2 120.3 . . ?
C8 N2 N3 115.73(12) . . ?
C10 N3 N2 114.52(12) . . ?
O1 N4 C14 118.31(12) . . ?
O2 N4 O1 123.69(13) . . ?
O2 N4 C14 118.00(12) . . ?
S1 C1 H1A 110.6 . . ?
S1 C1 H1B 110.6 . . ?
H1A C1 H1B 108.8 . . ?
C2 C1 S1 105.55(10) . . ?
C2 C1 H1A 110.6 . . ?
C2 C1 H1B 110.6 . . ?
C3 C2 C1 120.06(14) . . ?
C7 C2 C1 119.93(14) . . ?
C7 C2 C3 120.00(13) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.82(14) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.99(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.24(14) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.15(15) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 119.77(14) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
N1 C8 S1 116.84(11) . . ?
N1 C8 N2 121.05(13) . . ?
N2 C8 S1 122.06(11) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10 119.8 . . ?
N3 C10 C11 120.43(13) . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 117.47(13) . . ?
C12 C11 C16 120.03(13) . . ?
C16 C11 C10 122.49(13) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.72(13) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 121.2 . . ?
C12 C13 C14 117.68(14) . . ?
C14 C13 H13 121.2 . . ?
C13 C14 N4 117.82(13) . . ?
C15 C14 N4 119.02(12) . . ?
C15 C14 C13 123.16(13) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.41(13) . . ?
C16 C15 H15 120.8 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 119.98(14) . . ?
C15 C16 H16 120.0 . . ?
H1WA O1W H1WB 95.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1W 0.90 1.95 2.8173(16) 161.8 . yes
O1W H1WA Br1 0.85 2.47 3.2975(11) 165.6 . yes

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 C1 C2 C3 87.93(15) . . . . ?
S1 C1 C2 C7 -91.32(14) . . . . ?
O1 N4 C14 C13 2.01(19) . . . . ?
O1 N4 C14 C15 -178.33(13) . . . . ?
O2 N4 C14 C13 -177.99(13) . . . . ?
O2 N4 C14 C15 1.67(19) . . . . ?
N2 N3 C10 C11 178.93(12) . . . . ?
N3 N2 C8 S1 177.83(10) . . . . ?
N3 N2 C8 N1 0.4(2) . . . . ?
N3 C10 C11 C12 178.76(14) . . . . ?
N3 C10 C11 C16 -1.5(2) . . . . ?
N4 C14 C15 C16 -178.42(12) . . . . ?
C1 S1 C8 N1 175.71(11) . . . . ?
C1 S1 C8 N2 -1.82(14) . . . . ?
C1 C2 C3 C4 178.81(13) . . . . ?
C1 C2 C7 C6 -179.17(13) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C2 C7 C6 1.6(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C4 C5 C6 C7 -1.5(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C7 C2 C3 C4 -1.9(2) . . . . ?
C8 S1 C1 C2 -171.18(10) . . . . ?
C8 N2 N3 C10 -175.83(13) . . . . ?
C9 N1 C8 S1 -0.61(19) . . . . ?
C9 N1 C8 N2 176.95(13) . . . . ?
C10 C11 C12 C13 -179.25(13) . . . . ?
C10 C11 C16 C15 179.56(13) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C11 C16 C15 -0.7(2) . . . . ?
C12 C13 C14 N4 178.72(13) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C14 C15 C16 C11 -0.4(2) . . . . ?
C16 C11 C12 C13 1.0(2) . . . . ?

_olex2_submission_original_sample_id RKB_240517_SDc_SKVTL5
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.624
_oxdiff_exptl_absorpt_empirical_full_min 0.732
