# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_SSH-778
_database_code_depnum_ccdc_archive 'CCDC 2131973'
loop_
_audit_author_name
_audit_author_address
'Shuvendu Saha'
;PhD
India
;
_audit_update_record             
;
2022-01-02 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N3 O S'
_chemical_formula_sum            'C14 H15 N3 O S'
_chemical_formula_weight         273.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.831(4)
_cell_length_b                   9.988(7)
_cell_length_c                   14.908(7)
_cell_angle_alpha                91.97(2)
_cell_angle_beta                 97.090(12)
_cell_angle_gamma                103.993(18)
_cell_volume                     1406.3(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.666
_cell_measurement_theta_min      2.396
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1199 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.9494.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.043
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.747
_diffrn_reflns_theta_min         2.396
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4573
_reflns_number_total             5968
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.049
_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)+(0.0634P)²+0.6768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1451
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N2(H2), C4(H4), C18(H18), C11(H11), C21(H21), C17(H17), C25(H25),
 C16(H16), C7(H7), C9(H9), C8(H8), C2(H2A), C3(H3), C10(H10), C22(H22),
 C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S2 S -0.12992(7) 0.73861(6) 0.51051(4) 0.05693(18) Uani 1 1 d . . . . .
S1 S 0.37021(7) 0.42897(6) 0.81870(4) 0.05888(19) Uani 1 1 d . . . . .
N1 N 0.52681(19) 0.68911(18) 0.84922(11) 0.0449(4) Uani 1 1 d . . . . .
O2 O 0.2984(2) 0.79417(19) 0.59166(13) 0.0687(5) Uani 1 1 d . . . . .
N4 N 0.03542(18) 0.84397(18) 0.66525(11) 0.0443(4) Uani 1 1 d . . . . .
N5 N 0.18458(19) 0.96052(18) 0.55945(12) 0.0473(4) Uani 1 1 d . . . . .
H5 H 0.166794 1.020180 0.520359 0.057 Uiso 1 1 calc R . . . .
O1 O 0.77844(19) 0.5722(2) 0.82841(12) 0.0684(5) Uani 1 1 d . . . . .
N3 N 0.48858(19) 0.6008(2) 0.70126(12) 0.0487(4) Uani 1 1 d . . . . .
N2 N 0.66877(19) 0.57655(19) 0.95248(12) 0.0487(4) Uani 1 1 d . . . . .
H2 H 0.647992 0.537295 1.002666 0.058 Uiso 1 1 calc R . . . .
N6 N -0.0240(2) 0.60695(19) 0.64332(14) 0.0530(5) Uani 1 1 d . . . . .
C26 C -0.0363(2) 0.7244(2) 0.60873(14) 0.0429(4) Uani 1 1 d . . . . .
C6 C 0.8066(2) 0.4077(2) 0.93594(14) 0.0466(5) Uani 1 1 d . . . . .
C12 C 0.4658(2) 0.5751(2) 0.78554(13) 0.0435(5) Uani 1 1 d . . . . .
C20 C 0.3017(2) 0.8746(2) 0.44406(15) 0.0465(5) Uani 1 1 d . . . . .
C15 C 0.1307(2) 0.9593(2) 0.64221(15) 0.0459(5) Uani 1 1 d . . . . .
C19 C 0.2633(2) 0.8729(2) 0.53742(16) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.6169(2) 0.6906(2) 0.92882(14) 0.0477(5) Uani 1 1 d . . . . .
C5 C 0.7506(2) 0.5240(2) 0.90037(14) 0.0490(5) Uani 1 1 d . . . . .
C4 C 0.4983(3) 0.8178(2) 0.84339(16) 0.0544(5) Uani 1 1 d . . . . .
H4 H 0.440090 0.845213 0.795377 0.065 Uiso 1 1 calc R . . . .
C18 C 0.0049(3) 0.8700(3) 0.75146(15) 0.0544(5) Uani 1 1 d . . . . .
H18 H -0.056911 0.807897 0.784088 0.065 Uiso 1 1 calc R . . . .
C11 C 0.7505(3) 0.3254(3) 1.00182(17) 0.0590(6) Uani 1 1 d . . . . .
H11 H 0.669174 0.339602 1.025360 0.071 Uiso 1 1 calc R . . . .
C21 C 0.2187(3) 0.9092(3) 0.37099(17) 0.0605(6) Uani 1 1 d . . . . .
H21 H 0.136687 0.939577 0.379987 0.073 Uiso 1 1 calc R . . . .
C17 C 0.0789(3) 0.9994(3) 0.78068(17) 0.0645(7) Uani 1 1 d . . . . .
H17 H 0.076753 1.045169 0.837235 0.077 Uiso 1 1 calc R . . . .
C25 C 0.4213(3) 0.8314(3) 0.42929(18) 0.0616(6) Uani 1 1 d . . . . .
H25 H 0.478913 0.807341 0.478999 0.074 Uiso 1 1 calc R . . . .
C16 C 0.1602(3) 1.0554(3) 0.71271(18) 0.0610(6) Uani 1 1 d . . . . .
H16 H 0.223819 1.144214 0.715969 0.073 Uiso 1 1 calc R . . . .
C7 C 0.9230(3) 0.3818(3) 0.90191(17) 0.0608(6) Uani 1 1 d . . . . .
H7 H 0.961081 0.435348 0.855253 0.073 Uiso 1 1 calc R . . . .
C14 C 0.4138(3) 0.5043(3) 0.62571(16) 0.0707(7) Uani 1 1 d . . . . .
H14A H 0.443791 0.539871 0.568968 0.106 Uiso 1 1 calc R . . . .
H14B H 0.435577 0.414348 0.633627 0.106 Uiso 1 1 calc R . . . .
H14C H 0.311695 0.493580 0.623634 0.106 Uiso 1 1 calc R . . . .
C13 C 0.5977(3) 0.7172(3) 0.67711(17) 0.0639(7) Uani 1 1 d . . . . .
H13A H 0.594703 0.715087 0.611109 0.096 Uiso 1 1 calc R . . . .
H13B H 0.580265 0.804352 0.699067 0.096 Uiso 1 1 calc R . . . .
H13C H 0.691078 0.710001 0.705025 0.096 Uiso 1 1 calc R . . . .
C9 C 0.9295(3) 0.2008(3) 1.0001(2) 0.0686(7) Uani 1 1 d . . . . .
H9 H 0.971950 0.130553 1.022677 0.082 Uiso 1 1 calc R . . . .
C8 C 0.9852(3) 0.2798(3) 0.9344(2) 0.0673(7) Uani 1 1 d . . . . .
H8 H 1.066292 0.264769 0.911012 0.081 Uiso 1 1 calc R . . . .
C2 C 0.6428(3) 0.8184(3) 0.97135(17) 0.0634(6) Uani 1 1 d . . . . .
H2A H 0.701484 0.849176 1.027379 0.076 Uiso 1 1 calc R . . . .
C27 C 0.0858(3) 0.5995(3) 0.7172(2) 0.0738(8) Uani 1 1 d . . . . .
H27A H 0.075469 0.503084 0.732139 0.111 Uiso 1 1 calc R . . . .
H27B H 0.179212 0.635518 0.698492 0.111 Uiso 1 1 calc R . . . .
H27C H 0.076489 0.654953 0.770591 0.111 Uiso 1 1 calc R . . . .
C3 C 0.5676(3) 0.8976(3) 0.91796(18) 0.0649(7) Uani 1 1 d . . . . .
H3 H 0.565919 0.990672 0.931950 0.078 Uiso 1 1 calc R . . . .
C10 C 0.8126(3) 0.2224(3) 1.0335(2) 0.0707(7) Uani 1 1 d . . . . .
H10 H 0.773605 0.166457 1.078869 0.085 Uiso 1 1 calc R . . . .
C28 C -0.1153(3) 0.4744(3) 0.6044(2) 0.0787(8) Uani 1 1 d . . . . .
H28A H -0.091039 0.399420 0.638646 0.118 Uiso 1 1 calc R . . . .
H28B H -0.214381 0.473973 0.607575 0.118 Uiso 1 1 calc R . . . .
H28C H -0.101625 0.460990 0.541049 0.118 Uiso 1 1 calc R . . . .
C22 C 0.2556(4) 0.8994(3) 0.28444(19) 0.0756(8) Uani 1 1 d . . . . .
H22 H 0.198409 0.923354 0.234466 0.091 Uiso 1 1 calc R . . . .
C23 C 0.3731(4) 0.8557(3) 0.2703(2) 0.0754(8) Uani 1 1 d . . . . .
H23 H 0.396442 0.847795 0.210659 0.090 Uiso 1 1 calc R . . . .
C24 C 0.4577(3) 0.8230(3) 0.3430(2) 0.0742(8) Uani 1 1 d . . . . .
H24 H 0.540788 0.794818 0.333724 0.089 Uiso 1 1 calc R . . . .


_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
S2 C26 1.660(2) . ?
S1 C12 1.661(2) . ?
N1 C12 1.418(3) . ?
N1 C1 1.388(3) . ?
N1 C4 1.384(3) . ?
O2 C19 1.223(3) . ?
N4 C26 1.418(3) . ?
N4 C15 1.381(3) . ?
N4 C18 1.385(3) . ?
N5 H5 0.8800 . ?
N5 C15 1.401(3) . ?
N5 C19 1.358(3) . ?
O1 C5 1.225(3) . ?
N3 C12 1.326(3) . ?
N3 C14 1.455(3) . ?
N3 C13 1.468(3) . ?
N2 H2 0.8800 . ?
N2 C1 1.395(3) . ?
N2 C5 1.362(3) . ?
N6 C26 1.323(3) . ?
N6 C27 1.461(3) . ?
N6 C28 1.462(3) . ?
C6 C5 1.489(3) . ?
C6 C11 1.384(3) . ?
C6 C7 1.382(3) . ?
C20 C19 1.486(3) . ?
C20 C21 1.384(3) . ?
C20 C25 1.385(3) . ?
C15 C16 1.353(3) . ?
C1 C2 1.358(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.351(4) . ?
C18 H18 0.9500 . ?
C18 C17 1.348(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.414(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.382(4) . ?
C16 H16 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.381(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C8 1.364(4) . ?
C9 C10 1.368(4) . ?
C8 H8 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.409(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.366(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(4) . ?
C24 H24 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 N1 C12 127.19(18) . . ?
C4 N1 C12 124.23(18) . . ?
C4 N1 C1 108.49(18) . . ?
C15 N4 C26 127.56(18) . . ?
C15 N4 C18 108.50(18) . . ?
C18 N4 C26 123.46(18) . . ?
C15 N5 H5 118.8 . . ?
C19 N5 H5 118.8 . . ?
C19 N5 C15 122.31(18) . . ?
C12 N3 C14 120.8(2) . . ?
C12 N3 C13 124.09(19) . . ?
C14 N3 C13 114.9(2) . . ?
C1 N2 H2 119.0 . . ?
C5 N2 H2 119.0 . . ?
C5 N2 C1 122.09(19) . . ?
C26 N6 C27 123.1(2) . . ?
C26 N6 C28 120.9(2) . . ?
C27 N6 C28 115.8(2) . . ?
N4 C26 S2 120.42(15) . . ?
N6 C26 S2 125.63(17) . . ?
N6 C26 N4 113.91(19) . . ?
C11 C6 C5 123.9(2) . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 C11 118.2(2) . . ?
N1 C12 S1 120.17(15) . . ?
N3 C12 S1 126.01(17) . . ?
N3 C12 N1 113.76(19) . . ?
C21 C20 C19 122.8(2) . . ?
C21 C20 C25 119.0(2) . . ?
C25 C20 C19 118.1(2) . . ?
N4 C15 N5 121.04(18) . . ?
C16 C15 N4 108.0(2) . . ?
C16 C15 N5 130.9(2) . . ?
O2 C19 N5 121.3(2) . . ?
O2 C19 C20 121.7(2) . . ?
N5 C19 C20 117.05(18) . . ?
N1 C1 N2 122.11(19) . . ?
C2 C1 N1 107.4(2) . . ?
C2 C1 N2 130.5(2) . . ?
O1 C5 N2 121.4(2) . . ?
O1 C5 C6 121.8(2) . . ?
N2 C5 C6 116.84(19) . . ?
N1 C4 H4 126.0 . . ?
C3 C4 N1 108.0(2) . . ?
C3 C4 H4 126.0 . . ?
N4 C18 H18 126.2 . . ?
C17 C18 N4 107.6(2) . . ?
C17 C18 H18 126.2 . . ?
C6 C11 H11 119.9 . . ?
C6 C11 C10 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C18 C17 H17 125.9 . . ?
C18 C17 C16 108.3(2) . . ?
C16 C17 H17 125.9 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.7(3) . . ?
C24 C25 H25 119.6 . . ?
C15 C16 C17 107.5(2) . . ?
C15 C16 H16 126.2 . . ?
C17 C16 H16 126.2 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C1 C2 H2A 125.9 . . ?
C1 C2 C3 108.2(2) . . ?
C3 C2 H2A 125.9 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4 C3 C2 107.9(2) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
N6 C28 H28A 109.5 . . ?
N6 C28 H28B 109.5 . . ?
N6 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.7(3) . . ?
C24 C23 H23 120.2 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_SSH_842
_database_code_depnum_ccdc_archive 'CCDC 2131974'
loop_
_audit_author_name
_audit_author_address
'Shuvendu Saha'
;PhD
India
;
_audit_update_record             
;
2022-01-02 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_SSH_842             
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        30% Check
RESPONSE: This was developed due to the weakly diffracting nature of the crystal
;
# Added during the CSD deposition process: Sunday 02 January 2022 03:32 AM
# end Validation Reply Form

_audit_creation_date             2022-01-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N3 O S'
_chemical_formula_sum            'C14 H15 N3 O S'
_chemical_formula_weight         273.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.1959(7)
_cell_length_b                   9.4051(6)
_cell_length_c                   17.0462(15)
_cell_angle_alpha                81.503(6)
_cell_angle_beta                 82.539(7)
_cell_angle_gamma                82.743(6)
_cell_volume                     1437.12(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2356
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.2480
_cell_measurement_theta_min      2.1870
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_av_unetI/netI     0.1414
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31250
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.498
_diffrn_reflns_theta_min         2.203
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -0.34 119.66   0.50    6.00    --   28.00  59.94 -20.34  240
  2  ω     -0.34 119.66   0.50    6.00    --   28.00  59.94  69.66  240
  3  ω    -56.34  63.66   0.50    6.00    --  -28.00  59.94 159.66  240
  4  ω    -56.34  63.66   0.50    6.00    --  -28.00  59.94-110.34  240
  5  φ    -20.34 159.66   1.00    6.00 -20.34   0.00  59.94    --   180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0370467000
_diffrn_orient_matrix_UB_12      0.0575850000
_diffrn_orient_matrix_UB_13      -0.0219618000
_diffrn_orient_matrix_UB_21      0.0553068000
_diffrn_orient_matrix_UB_22      -0.0506824000
_diffrn_orient_matrix_UB_23      -0.0161780000
_diffrn_orient_matrix_UB_31      -0.0411494000
_diffrn_orient_matrix_UB_32      -0.0003376000
_diffrn_orient_matrix_UB_33      -0.0323890000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3637
_reflns_number_total             12300
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.204
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         12300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2145
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      0.934
_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)+(0.0564P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.2289
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C25(H25), C2(H2A), C11(H11), C24(H24), C21(H21), C3(H3),
 C4(H4), C17(H17), C23(H23), C22(H22), C7(H7), C10(H10), C15(H15), C16(H16),
 C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C14(H14A,H14B,
 H14C)
;
_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 0.90797(9) 0.23100(9) 0.08939(5) 0.0831(3) Uani 1 1 d . . . . .
S2 S 0.31979(13) 0.82343(14) 0.13140(6) 0.1274(4) Uani 1 1 d . . . . .
O2 O 0.42445(18) 0.64029(17) 0.31483(10) 0.0618(4) Uani 1 1 d . . . . .
O1 O 0.6227(2) 0.13707(17) 0.24861(10) 0.0665(5) Uani 1 1 d . . . . .
N1 N 0.7558(2) 0.0012(2) 0.11709(12) 0.0575(5) Uani 1 1 d . . . . .
N2 N 0.5239(2) -0.0672(2) 0.30761(11) 0.0598(5) Uani 1 1 d . . . . .
H2 H 0.523967 -0.159943 0.304856 0.072 Uiso 1 1 calc R U . . .
N5 N 0.5622(2) 0.4280(2) 0.29421(12) 0.0565(5) Uani 1 1 d . . . . .
H5 H 0.571469 0.357622 0.264550 0.068 Uiso 1 1 calc R U . . .
N4 N 0.2264(2) 0.5800(2) 0.20975(13) 0.0650(6) Uani 1 1 d . . . . .
N6 N 0.1072(3) 0.7928(2) 0.25135(14) 0.0701(6) Uani 1 1 d . . . . .
N3 N 0.6261(3) 0.2220(3) 0.07561(13) 0.0749(6) Uani 1 1 d . . . . .
C5 C 0.6099(2) 0.0080(2) 0.24966(13) 0.0509(5) Uani 1 1 d . . . . .
C20 C 0.6758(3) 0.4255(2) 0.34305(14) 0.0525(5) Uani 1 1 d . . . . .
C1 C 0.6858(2) -0.0715(2) 0.18683(13) 0.0516(5) Uani 1 1 d . . . . .
C19 C 0.4412(2) 0.5248(2) 0.28728(13) 0.0506(5) Uani 1 1 d . . . . .
C12 C 0.7548(3) 0.1551(3) 0.09435(14) 0.0592(6) Uani 1 1 d . . . . .
C18 C 0.3313(3) 0.4811(3) 0.24376(15) 0.0588(6) Uani 1 1 d . . . . .
C6 C 0.4340(3) -0.0109(2) 0.37207(13) 0.0563(6) Uani 1 1 d . . . . .
C25 C 0.8091(3) 0.3451(3) 0.32302(16) 0.0640(6) Uani 1 1 d . . . . .
H25 H 0.823715 0.300450 0.275720 0.077 Uiso 1 1 calc R U . . .
C2 C 0.7121(3) -0.2170(3) 0.17986(16) 0.0628(6) Uani 1 1 d . . . . .
H2A H 0.678816 -0.293443 0.218217 0.075 Uiso 1 1 calc R U . . .
C26 C 0.2134(3) 0.7359(3) 0.20064(16) 0.0687(7) Uani 1 1 d . . . . .
C11 C 0.4670(3) 0.1066(3) 0.40529(15) 0.0717(7) Uani 1 1 d . . . . .
H11 H 0.554677 0.150281 0.385982 0.086 Uiso 1 1 calc R U . . .
C24 C 0.9209(3) 0.3299(3) 0.37171(18) 0.0745(8) Uani 1 1 d . . . . .
H24 H 1.012092 0.275004 0.357575 0.089 Uiso 1 1 calc R U . . .
C21 C 0.6559(3) 0.4911(3) 0.41177(15) 0.0689(7) Uani 1 1 d . . . . .
H21 H 0.565879 0.547775 0.425955 0.083 Uiso 1 1 calc R U . . .
C3 C 0.7964(3) -0.2326(3) 0.10643(18) 0.0733(8) Uani 1 1 d . . . . .
H3 H 0.830082 -0.321275 0.086176 0.088 Uiso 1 1 calc R U . . .
C4 C 0.8215(3) -0.0979(3) 0.06918(17) 0.0718(7) Uani 1 1 d . . . . .
H4 H 0.875815 -0.076709 0.018303 0.086 Uiso 1 1 calc R U . . .
C17 C 0.3043(3) 0.3469(3) 0.2304(2) 0.0819(9) Uani 1 1 d . . . . .
H17 H 0.358402 0.257429 0.247906 0.098 Uiso 1 1 calc R U . . .
C23 C 0.9007(3) 0.3933(3) 0.44001(19) 0.0796(8) Uani 1 1 d . . . . .
H23 H 0.977287 0.382285 0.473590 0.095 Uiso 1 1 calc R U . . .
C22 C 0.7698(4) 0.4725(3) 0.45953(19) 0.0831(9) Uani 1 1 d . . . . .
H22 H 0.756134 0.516126 0.507162 0.100 Uiso 1 1 calc R U . . .
C7 C 0.3102(3) -0.0788(3) 0.40406(18) 0.0746(8) Uani 1 1 d . . . . .
H7 H 0.288184 -0.160618 0.382977 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3715(4) 0.1586(3) 0.46623(17) 0.0880(10) Uani 1 1 d . . . . .
H10 H 0.391567 0.241432 0.487112 0.106 Uiso 1 1 calc R U . . .
C15 C 0.1384(3) 0.5066(4) 0.1740(2) 0.0897(10) Uani 1 1 d . . . . .
H15 H 0.058742 0.549303 0.145081 0.108 Uiso 1 1 calc R U . . .
C16 C 0.1837(3) 0.3647(4) 0.1869(2) 0.0992(12) Uani 1 1 d . . . . .
H16 H 0.141104 0.289675 0.169352 0.119 Uiso 1 1 calc R U . . .
C28 C 0.0251(3) 0.7085(4) 0.31710(19) 0.0902(9) Uani 1 1 d . . . . .
H28A H -0.080075 0.723320 0.309985 0.135 Uiso 1 1 calc R U . . .
H28B H 0.039110 0.739894 0.367677 0.135 Uiso 1 1 calc R U . . .
H28C H 0.060930 0.605758 0.317867 0.135 Uiso 1 1 calc R U . . .
C13 C 0.4969(3) 0.1495(4) 0.07037(19) 0.0913(10) Uani 1 1 d . . . . .
H13A H 0.526743 0.046094 0.068908 0.137 Uiso 1 1 calc R U . . .
H13B H 0.452601 0.191314 0.021667 0.137 Uiso 1 1 calc R U . . .
H13C H 0.424585 0.162575 0.117033 0.137 Uiso 1 1 calc R U . . .
C8 C 0.2184(4) -0.0260(4) 0.4674(2) 0.0961(10) Uani 1 1 d . . . . .
H8 H 0.134370 -0.073486 0.489885 0.115 Uiso 1 1 calc R U . . .
C9 C 0.2471(4) 0.0924(4) 0.4975(2) 0.0991(11) Uani 1 1 d . . . . .
H9 H 0.182040 0.129199 0.539590 0.119 Uiso 1 1 calc R U . . .
C27 C 0.0715(4) 0.9506(3) 0.2431(3) 0.1171(13) Uani 1 1 d . . . . .
H27A H 0.153794 0.994802 0.257274 0.176 Uiso 1 1 calc R U . . .
H27B H -0.017732 0.975023 0.278839 0.176 Uiso 1 1 calc R U . . .
H27C H 0.054580 0.987186 0.187825 0.176 Uiso 1 1 calc R U . . .
C14 C 0.6098(4) 0.3792(4) 0.0579(3) 0.1242(14) Uani 1 1 d . . . . .
H14A H 0.665337 0.419644 0.093049 0.186 Uiso 1 1 calc R U . . .
H14B H 0.505278 0.415933 0.066593 0.186 Uiso 1 1 calc R U . . .
H14C H 0.647992 0.407617 0.002124 0.186 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 C12 1.645(3) . ?
S2 C26 1.626(3) . ?
O2 C19 1.230(2) . ?
O1 C5 1.232(2) . ?
N1 C1 1.403(3) . ?
N1 C12 1.441(3) . ?
N1 C4 1.362(3) . ?
N2 H2 0.8800 . ?
N2 C5 1.354(3) . ?
N2 C6 1.413(3) . ?
N5 H5 0.8800 . ?
N5 C20 1.413(3) . ?
N5 C19 1.352(3) . ?
N4 C18 1.375(3) . ?
N4 C26 1.442(3) . ?
N4 C15 1.378(3) . ?
N6 C26 1.331(3) . ?
N6 C28 1.457(4) . ?
N6 C27 1.468(4) . ?
N3 C12 1.323(3) . ?
N3 C13 1.461(4) . ?
N3 C14 1.457(4) . ?
C5 C1 1.450(3) . ?
C20 C25 1.387(3) . ?
C20 C21 1.384(3) . ?
C1 C2 1.380(3) . ?
C19 C18 1.460(3) . ?
C18 C17 1.373(3) . ?
C6 C11 1.396(3) . ?
C6 C7 1.385(3) . ?
C25 H25 0.9500 . ?
C25 C24 1.384(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.401(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.377(4) . ?
C24 H24 0.9500 . ?
C24 C23 1.366(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.364(4) . ?
C4 H4 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.393(4) . ?
C23 H23 0.9500 . ?
C23 C22 1.363(4) . ?
C22 H22 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.393(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.380(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.341(4) . ?
C16 H16 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.361(4) . ?
C9 H9 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C1 N1 C12 127.74(19) . . ?
C4 N1 C1 108.9(2) . . ?
C4 N1 C12 123.3(2) . . ?
C5 N2 H2 116.9 . . ?
C5 N2 C6 126.17(19) . . ?
C6 N2 H2 116.9 . . ?
C20 N5 H5 115.9 . . ?
C19 N5 H5 115.9 . . ?
C19 N5 C20 128.23(19) . . ?
C18 N4 C26 129.4(2) . . ?
C18 N4 C15 108.2(2) . . ?
C15 N4 C26 121.9(2) . . ?
C26 N6 C28 124.1(2) . . ?
C26 N6 C27 119.0(3) . . ?
C28 N6 C27 116.8(3) . . ?
C12 N3 C13 124.7(3) . . ?
C12 N3 C14 118.7(3) . . ?
C14 N3 C13 116.6(3) . . ?
O1 C5 N2 122.9(2) . . ?
O1 C5 C1 120.9(2) . . ?
N2 C5 C1 116.20(19) . . ?
C25 C20 N5 117.5(2) . . ?
C21 C20 N5 122.9(2) . . ?
C21 C20 C25 119.5(2) . . ?
N1 C1 C5 120.7(2) . . ?
C2 C1 N1 106.5(2) . . ?
C2 C1 C5 132.8(2) . . ?
O2 C19 N5 123.3(2) . . ?
O2 C19 C18 122.5(2) . . ?
N5 C19 C18 114.21(19) . . ?
N1 C12 S1 119.87(19) . . ?
N3 C12 S1 125.8(2) . . ?
N3 C12 N1 114.3(2) . . ?
N4 C18 C19 121.7(2) . . ?
C17 C18 N4 107.1(2) . . ?
C17 C18 C19 131.1(2) . . ?
C11 C6 N2 122.8(2) . . ?
C7 C6 N2 117.7(2) . . ?
C7 C6 C11 119.5(2) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C1 C2 H2A 125.9 . . ?
C1 C2 C3 108.2(2) . . ?
C3 C2 H2A 125.9 . . ?
N4 C26 S2 119.8(2) . . ?
N6 C26 S2 126.8(2) . . ?
N6 C26 N4 113.3(2) . . ?
C6 C11 H11 120.2 . . ?
C10 C11 C6 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C2 C3 H3 126.1 . . ?
C4 C3 C2 107.9(2) . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C3 108.6(2) . . ?
N1 C4 H4 125.7 . . ?
C3 C4 H4 125.7 . . ?
C18 C17 H17 126.0 . . ?
C18 C17 C16 108.1(3) . . ?
C16 C17 H17 126.0 . . ?
C24 C23 H23 120.3 . . ?
C22 C23 C24 119.4(3) . . ?
C22 C23 H23 120.3 . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.8(3) . . ?
C23 C22 H22 119.1 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.5(3) . . ?
C8 C7 H7 120.3 . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
N4 C15 H15 125.6 . . ?
C16 C15 N4 108.7(3) . . ?
C16 C15 H15 125.6 . . ?
C17 C16 H16 126.1 . . ?
C15 C16 C17 107.8(2) . . ?
C15 C16 H16 126.1 . . ?
N6 C28 H28A 109.5 . . ?
N6 C28 H28B 109.5 . . ?
N6 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C10 C9 H9 120.3 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O2 C19 C18 N4 20.3(4) . . . . ?
O2 C19 C18 C17 -156.8(3) . . . . ?
O1 C5 C1 N1 -10.5(3) . . . . ?
O1 C5 C1 C2 166.8(3) . . . . ?
N1 C1 C2 C3 -0.4(3) . . . . ?
N2 C5 C1 N1 168.5(2) . . . . ?
N2 C5 C1 C2 -14.2(4) . . . . ?
N2 C6 C11 C10 177.8(3) . . . . ?
N2 C6 C7 C8 -179.6(3) . . . . ?
N5 C20 C25 C24 -175.3(2) . . . . ?
N5 C20 C21 C22 174.6(2) . . . . ?
N5 C19 C18 N4 -159.5(2) . . . . ?
N5 C19 C18 C17 23.4(4) . . . . ?
N4 C18 C17 C16 1.0(4) . . . . ?
N4 C15 C16 C17 -1.0(4) . . . . ?
C5 N2 C6 C11 -29.1(4) . . . . ?
C5 N2 C6 C7 152.4(3) . . . . ?
C5 C1 C2 C3 -178.0(2) . . . . ?
C20 N5 C19 O2 11.7(4) . . . . ?
C20 N5 C19 C18 -168.5(2) . . . . ?
C20 C25 C24 C23 0.2(4) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C1 N1 C12 S1 112.8(2) . . . . ?
C1 N1 C12 N3 -70.0(3) . . . . ?
C1 N1 C4 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C19 N5 C20 C25 -160.4(2) . . . . ?
C19 N5 C20 C21 23.9(4) . . . . ?
C19 C18 C17 C16 178.5(3) . . . . ?
C12 N1 C1 C5 -5.1(3) . . . . ?
C12 N1 C1 C2 176.9(2) . . . . ?
C12 N1 C4 C3 -177.0(2) . . . . ?
C18 N4 C26 S2 76.8(3) . . . . ?
C18 N4 C26 N6 -105.0(3) . . . . ?
C18 N4 C15 C16 1.6(4) . . . . ?
C18 C17 C16 C15 0.0(4) . . . . ?
C6 N2 C5 O1 2.5(4) . . . . ?
C6 N2 C5 C1 -176.5(2) . . . . ?
C6 C11 C10 C9 3.0(5) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C25 C20 C21 C22 -1.0(4) . . . . ?
C25 C24 C23 C22 -0.4(5) . . . . ?
C2 C3 C4 N1 0.1(3) . . . . ?
C26 N4 C18 C19 8.4(4) . . . . ?
C26 N4 C18 C17 -173.8(3) . . . . ?
C26 N4 C15 C16 174.5(3) . . . . ?
C11 C6 C7 C8 1.8(4) . . . . ?
C11 C10 C9 C8 -0.1(5) . . . . ?
C24 C23 C22 C21 -0.2(5) . . . . ?
C21 C20 C25 C24 0.5(4) . . . . ?
C4 N1 C1 C5 178.4(2) . . . . ?
C4 N1 C1 C2 0.4(3) . . . . ?
C4 N1 C12 S1 -71.1(3) . . . . ?
C4 N1 C12 N3 106.0(3) . . . . ?
C7 C6 C11 C10 -3.8(4) . . . . ?
C7 C8 C9 C10 -1.9(6) . . . . ?
C15 N4 C18 C19 -179.3(2) . . . . ?
C15 N4 C18 C17 -1.6(3) . . . . ?
C15 N4 C26 S2 -94.5(3) . . . . ?
C15 N4 C26 N6 83.6(3) . . . . ?
C28 N6 C26 S2 -173.8(2) . . . . ?
C28 N6 C26 N4 8.2(4) . . . . ?
C13 N3 C12 S1 171.5(2) . . . . ?
C13 N3 C12 N1 -5.5(4) . . . . ?
C27 N6 C26 S2 4.3(4) . . . . ?
C27 N6 C26 N4 -173.7(2) . . . . ?
C14 N3 C12 S1 -7.8(4) . . . . ?
C14 N3 C12 N1 175.2(3) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.626
_oxdiff_exptl_absorpt_empirical_full_min 0.252
