# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_apsp42
_database_code_depnum_ccdc_archive 'CCDC 2371891'
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 Cl N3 O S'
_chemical_formula_sum            'C23 H20 Cl N3 O S'
_chemical_formula_weight         421.93
_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'
Cl Cl 0.1484 0.1585 '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                   5.4212(11)
_cell_length_b                   12.849(3)
_cell_length_c                   15.183(3)
_cell_angle_alpha                82.858(8)
_cell_angle_beta                 81.299(8)
_cell_angle_gamma                87.732(9)
_cell_volume                     1037.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6196
_cell_measurement_temperature    175.29
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4937
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1509 before and 0.0920 after correction.
The Ratio of minimum to maximum transmission is 0.6622.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11618
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.248
_diffrn_reflns_theta_min         2.997
_diffrn_ambient_temperature      175.29
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3577
_reflns_number_total             4541
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.010(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0929P)²+0.2290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1782
_refine_special_details          ?
_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:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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
Cl1 Cl -0.18485(12) 0.82554(7) 1.05797(4) 0.0673(3) Uani 1 1 d . . . . .
S1 S -0.64562(10) 0.79880(5) 0.70628(4) 0.0443(2) Uani 1 1 d . . . . .
O1 O 0.5637(3) 0.55833(13) 0.37104(13) 0.0586(5) Uani 1 1 d . . . . .
N1 N 0.9048(3) 0.64272(14) 0.28462(13) 0.0431(4) Uani 1 1 d . . . . .
N2 N 0.4247(3) 0.77816(14) 0.41518(11) 0.0401(4) Uani 1 1 d . . . . .
N3 N 0.2645(3) 0.70468(15) 0.45450(12) 0.0430(4) Uani 1 1 d . . . . .
H3 H 0.294224 0.638993 0.444598 0.052 Uiso 1 1 calc R U . . .
C1 C 0.6844(4) 0.63765(17) 0.34252(15) 0.0426(5) Uani 1 1 d . . . . .
C2 C 0.6207(4) 0.74689(16) 0.36329(14) 0.0375(5) Uani 1 1 d . . . . .
C3 C 0.8194(4) 0.81219(16) 0.31414(13) 0.0364(4) Uani 1 1 d . . . . .
C4 C 0.9906(4) 0.74647(16) 0.26738(13) 0.0371(5) Uani 1 1 d . . . . .
C5 C 1.2067(4) 0.78420(18) 0.21497(14) 0.0429(5) Uani 1 1 d . . . . .
H5 H 1.322087 0.739040 0.183756 0.051 Uiso 1 1 calc R U . . .
C6 C 1.2483(4) 0.89095(19) 0.20980(15) 0.0470(5) Uani 1 1 d . . . . .
H6 H 1.395768 0.919257 0.174557 0.056 Uiso 1 1 calc R U . . .
C7 C 1.0802(4) 0.95682(18) 0.25474(16) 0.0471(5) Uani 1 1 d . . . . .
H7 H 1.113042 1.029598 0.249264 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8647(4) 0.91854(17) 0.30763(15) 0.0425(5) Uani 1 1 d . . . . .
H8 H 0.750235 0.964106 0.338770 0.051 Uiso 1 1 calc R U . . .
C9 C 1.0361(5) 0.55090(18) 0.24974(17) 0.0513(6) Uani 1 1 d . . . . .
H9A H 0.964540 0.486587 0.285657 0.062 Uiso 1 1 calc R U . . .
H9B H 1.213855 0.552658 0.257552 0.062 Uiso 1 1 calc R U . . .
C10 C 1.0210(5) 0.5449(2) 0.15172(19) 0.0578(7) Uani 1 1 d . . . . .
H10A H 1.077062 0.612010 0.116438 0.069 Uiso 1 1 calc R U . . .
H10B H 1.136803 0.488694 0.130426 0.069 Uiso 1 1 calc R U . . .
C11 C 0.7621(6) 0.5233(3) 0.1344(3) 0.0836(10) Uani 1 1 d . . . . .
H11A H 0.765651 0.517797 0.070400 0.125 Uiso 1 1 calc R U . . .
H11B H 0.648113 0.580724 0.151919 0.125 Uiso 1 1 calc R U . . .
H11C H 0.704304 0.457287 0.169596 0.125 Uiso 1 1 calc R U . . .
C12 C 0.0505(4) 0.73065(17) 0.51112(13) 0.0380(5) Uani 1 1 d . . . . .
C13 C -0.0072(4) 0.83312(17) 0.52936(14) 0.0427(5) Uani 1 1 d . . . . .
H13 H 0.099691 0.888695 0.502242 0.051 Uiso 1 1 calc R U . . .
C14 C -0.2213(4) 0.85324(16) 0.58729(15) 0.0421(5) Uani 1 1 d . . . . .
H14 H -0.260717 0.923144 0.599671 0.051 Uiso 1 1 calc R U . . .
C15 C -0.3795(4) 0.77316(16) 0.62763(13) 0.0379(5) Uani 1 1 d . . . . .
C16 C -0.3245(4) 0.67155(17) 0.60740(14) 0.0421(5) Uani 1 1 d . . . . .
H16 H -0.433287 0.616238 0.633533 0.051 Uiso 1 1 calc R U . . .
C17 C -0.1118(4) 0.65102(17) 0.54933(15) 0.0442(5) Uani 1 1 d . . . . .
H17 H -0.075895 0.581484 0.535303 0.053 Uiso 1 1 calc R U . . .
C18 C -0.5086(4) 0.80334(16) 0.80488(13) 0.0358(4) Uani 1 1 d . . . . .
C19 C -0.2955(4) 0.74557(18) 0.82208(15) 0.0437(5) Uani 1 1 d . . . . .
H19 H -0.216221 0.701717 0.779743 0.052 Uiso 1 1 calc R U . . .
C20 C -0.1981(4) 0.75132(19) 0.90001(16) 0.0476(5) Uani 1 1 d . . . . .
H20 H -0.051470 0.712178 0.911359 0.057 Uiso 1 1 calc R U . . .
C21 C -0.3165(4) 0.81496(19) 0.96176(15) 0.0448(5) Uani 1 1 d . . . . .
C22 C -0.5302(4) 0.87090(19) 0.94708(15) 0.0465(5) Uani 1 1 d . . . . .
H22 H -0.611629 0.912728 0.990646 0.056 Uiso 1 1 calc R U . . .
C23 C -0.6264(4) 0.86598(18) 0.86837(15) 0.0426(5) Uani 1 1 d . . . . .
H23 H -0.773032 0.905346 0.857468 0.051 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
Cl1 C21 1.742(2) . ?
S1 C15 1.776(2) . ?
S1 C18 1.777(2) . ?
O1 C1 1.229(3) . ?
N1 C1 1.371(3) . ?
N1 C4 1.410(3) . ?
N1 C9 1.468(3) . ?
N2 N3 1.330(3) . ?
N2 C2 1.305(3) . ?
N3 H3 0.8800 . ?
N3 C12 1.391(3) . ?
C1 C2 1.492(3) . ?
C2 C3 1.447(3) . ?
C3 C4 1.402(3) . ?
C3 C8 1.387(3) . ?
C4 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.514(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.509(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.393(3) . ?
C12 C17 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 C23 1.397(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 C22 1.371(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(3) . ?
C23 H23 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
C15 S1 C18 101.31(9) . . ?
C1 N1 C4 110.61(17) . . ?
C1 N1 C9 123.82(19) . . ?
C4 N1 C9 125.51(19) . . ?
C2 N2 N3 116.61(18) . . ?
N2 N3 H3 119.7 . . ?
N2 N3 C12 120.66(18) . . ?
C12 N3 H3 119.7 . . ?
O1 C1 N1 126.3(2) . . ?
O1 C1 C2 127.2(2) . . ?
N1 C1 C2 106.49(18) . . ?
N2 C2 C1 127.15(19) . . ?
N2 C2 C3 126.39(18) . . ?
C3 C2 C1 106.46(17) . . ?
C4 C3 C2 107.18(17) . . ?
C8 C3 C2 133.06(19) . . ?
C8 C3 C4 119.75(19) . . ?
C3 C4 N1 109.25(17) . . ?
C5 C4 N1 128.81(19) . . ?
C5 C4 C3 121.94(19) . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.2(2) . . ?
C6 C5 H5 121.4 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 H8 120.7 . . ?
C7 C8 C3 118.5(2) . . ?
C7 C8 H8 120.7 . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
N1 C9 C10 113.7(2) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.4(2) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 122.41(19) . . ?
C17 C12 N3 118.18(19) . . ?
C17 C12 C13 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.16(19) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 S1 120.79(16) . . ?
C14 C15 C16 119.17(19) . . ?
C16 C15 S1 120.02(16) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 119.6 . . ?
C19 C18 S1 122.92(16) . . ?
C19 C18 C23 119.2(2) . . ?
C23 C18 S1 117.82(16) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.56(19) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.3(2) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 Cl1 118.81(18) . . ?
C22 C21 Cl1 119.99(17) . . ?
C22 C21 C20 121.2(2) . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(2) . . ?
C23 C22 H22 120.2 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.2(2) . . ?
C22 C23 H23 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
Cl1 C21 C22 C23 176.81(18) . . . . ?
S1 C15 C16 C17 -177.14(17) . . . . ?
S1 C18 C19 C20 -179.46(18) . . . . ?
S1 C18 C23 C22 178.84(17) . . . . ?
O1 C1 C2 N2 -0.4(4) . . . . ?
O1 C1 C2 C3 179.8(2) . . . . ?
N1 C1 C2 N2 179.3(2) . . . . ?
N1 C1 C2 C3 -0.4(2) . . . . ?
N1 C4 C5 C6 -179.4(2) . . . . ?
N1 C9 C10 C11 -68.4(3) . . . . ?
N2 N3 C12 C13 0.1(3) . . . . ?
N2 N3 C12 C17 179.12(19) . . . . ?
N2 C2 C3 C4 -180.0(2) . . . . ?
N2 C2 C3 C8 1.0(4) . . . . ?
N3 N2 C2 C1 0.5(3) . . . . ?
N3 N2 C2 C3 -179.73(19) . . . . ?
N3 C12 C13 C14 -179.1(2) . . . . ?
N3 C12 C17 C16 178.7(2) . . . . ?
C1 N1 C4 C3 -1.0(2) . . . . ?
C1 N1 C4 C5 178.2(2) . . . . ?
C1 N1 C9 C10 107.5(3) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C1 C2 C3 C8 -179.2(2) . . . . ?
C2 N2 N3 C12 179.86(18) . . . . ?
C2 C3 C4 N1 0.7(2) . . . . ?
C2 C3 C4 C5 -178.57(19) . . . . ?
C2 C3 C8 C7 178.7(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 N1 C1 O1 -179.4(2) . . . . ?
C4 N1 C1 C2 0.9(2) . . . . ?
C4 N1 C9 C10 -75.6(3) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C8 C3 C4 N1 179.87(19) . . . . ?
C8 C3 C4 C5 0.6(3) . . . . ?
C9 N1 C1 O1 -2.2(4) . . . . ?
C9 N1 C1 C2 178.12(19) . . . . ?
C9 N1 C4 C3 -178.2(2) . . . . ?
C9 N1 C4 C5 1.0(4) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C12 C17 C16 -2.2(3) . . . . ?
C13 C14 C15 S1 176.80(17) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C15 S1 C18 C19 -30.3(2) . . . . ?
C15 S1 C18 C23 151.42(17) . . . . ?
C15 C16 C17 C12 0.6(3) . . . . ?
C17 C12 C13 C14 1.9(3) . . . . ?
C18 S1 C15 C14 -79.67(19) . . . . ?
C18 S1 C15 C16 98.84(19) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C18 C23 C22 0.5(3) . . . . ?
C19 C20 C21 Cl1 -177.54(18) . . . . ?
C19 C20 C21 C22 0.9(4) . . . . ?
C20 C21 C22 C23 -1.6(4) . . . . ?
C21 C22 C23 C18 0.9(4) . . . . ?
C23 C18 C19 C20 -1.2(3) . . . . ?

_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_arunap
_database_code_depnum_ccdc_archive 'CCDC 2371892'
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_audit_creation_date             2024-06-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H22 N2 O3 S'
_chemical_formula_sum            'C30 H22 N2 O3 S'
_chemical_formula_weight         490.55
_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                   7.8820(11)
_cell_length_b                   10.6903(15)
_cell_length_c                   15.608(2)
_cell_angle_alpha                81.608(5)
_cell_angle_beta                 82.326(5)
_cell_angle_gamma                68.920(5)
_cell_volume                     1209.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5062
_cell_measurement_temperature    298.95
_cell_measurement_theta_max      28.90
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.3155
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1641 before and 0.0981 after correction.
The Ratio of minimum to maximum transmission is 0.4230.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15750
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.139
_diffrn_reflns_theta_min         2.648
_diffrn_ambient_temperature      298.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3718
_reflns_number_total             6425
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.035(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.046
_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)+(0.1109P)²+0.1566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1890
_refine_ls_wR_factor_ref         0.2350
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C30(H30A,H30B,H30C)
;
_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 0.29801(10) 0.84541(8) 0.00219(4) 0.0580(3) Uani 1 1 d . . . . .
O1 O 0.2461(2) 0.50782(17) 0.59028(10) 0.0468(4) Uani 1 1 d . . . . .
O2 O 0.1812(3) 0.3270(2) 0.64333(12) 0.0643(6) Uani 1 1 d . . . . .
O3 O 0.3121(3) 0.9761(2) 0.80425(11) 0.0595(5) Uani 1 1 d . . . . .
N1 N 0.2910(3) 0.6814(2) 0.38566(12) 0.0453(5) Uani 1 1 d . . . . .
N2 N 0.3008(3) 0.7727(2) 0.43527(12) 0.0479(5) Uani 1 1 d . . . . .
C1 C 0.2101(3) 0.3952(3) 0.57842(15) 0.0457(6) Uani 1 1 d . . . . .
C2 C 0.2684(3) 0.5939(2) 0.51876(14) 0.0415(5) Uani 1 1 d . . . . .
C3 C 0.2702(3) 0.5699(3) 0.43481(14) 0.0410(5) Uani 1 1 d . . . . .
C4 C 0.2453(3) 0.4508(2) 0.41482(15) 0.0406(5) Uani 1 1 d . . . . .
C5 C 0.2107(3) 0.3667(2) 0.48891(15) 0.0437(6) Uani 1 1 d . . . . .
C6 C 0.1767(4) 0.2504(3) 0.47841(18) 0.0509(6) Uani 1 1 d . . . . .
H6 H 0.150105 0.196974 0.527120 0.061 Uiso 1 1 calc R U . . .
C7 C 0.1821(4) 0.2143(3) 0.39690(18) 0.0555(7) Uani 1 1 d . . . . .
H7 H 0.160886 0.136231 0.390382 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2196(4) 0.2955(3) 0.32408(18) 0.0552(7) Uani 1 1 d . . . . .
H8 H 0.224836 0.270620 0.268865 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2488(4) 0.4119(3) 0.33284(16) 0.0509(6) Uani 1 1 d . . . . .
H9 H 0.271356 0.465650 0.283383 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2873(3) 0.7201(3) 0.51865(15) 0.0419(5) Uani 1 1 d . . . . .
C11 C 0.2931(3) 0.7895(3) 0.59100(15) 0.0422(5) Uani 1 1 d . . . . .
C12 C 0.2449(4) 0.7461(3) 0.67650(16) 0.0520(7) Uani 1 1 d . . . . .
H12 H 0.206626 0.672022 0.686984 0.062 Uiso 1 1 calc R U . . .
C13 C 0.2524(4) 0.8096(3) 0.74536(16) 0.0524(7) Uani 1 1 d . . . . .
H13 H 0.219332 0.778513 0.801595 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3096(3) 0.9210(3) 0.73124(15) 0.0449(6) Uani 1 1 d . . . . .
C15 C 0.3562(4) 0.9668(3) 0.64690(16) 0.0489(6) Uani 1 1 d . . . . .
H15 H 0.392984 1.041483 0.636506 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3480(4) 0.9017(3) 0.57836(16) 0.0474(6) Uani 1 1 d . . . . .
H16 H 0.380055 0.933503 0.522127 0.057 Uiso 1 1 calc R U . . .
C17 C 0.3860(6) 1.0808(3) 0.7959(2) 0.0777(10) Uani 1 1 d . . . . .
H17A H 0.310905 1.158352 0.761917 0.117 Uiso 1 1 calc R U . . .
H17B H 0.507427 1.050588 0.767591 0.117 Uiso 1 1 calc R U . . .
H17C H 0.389716 1.104242 0.852520 0.117 Uiso 1 1 calc R U . . .
C18 C 0.2952(3) 0.7153(3) 0.29298(14) 0.0436(6) Uani 1 1 d . . . . .
C19 C 0.4474(4) 0.6548(3) 0.24080(15) 0.0482(6) Uani 1 1 d . . . . .
H19 H 0.547830 0.589157 0.265002 0.058 Uiso 1 1 calc R U . . .
C20 C 0.4530(3) 0.6908(3) 0.15152(15) 0.0461(6) Uani 1 1 d . . . . .
H20 H 0.556845 0.648655 0.116119 0.055 Uiso 1 1 calc R U . . .
C21 C 0.3043(3) 0.7894(3) 0.11505(15) 0.0442(6) Uani 1 1 d . . . . .
C22 C 0.1507(4) 0.8500(3) 0.16882(17) 0.0646(8) Uani 1 1 d . . . . .
H22 H 0.050010 0.915985 0.145058 0.078 Uiso 1 1 calc R U . . .
C23 C 0.1454(4) 0.8133(3) 0.25763(17) 0.0652(9) Uani 1 1 d . . . . .
H23 H 0.041595 0.854442 0.293379 0.078 Uiso 1 1 calc R U . . .
C24 C 0.5226(4) 0.7529(3) -0.03995(15) 0.0491(6) Uani 1 1 d . . . . .
C25 C 0.5590(4) 0.6286(3) -0.06882(17) 0.0559(7) Uani 1 1 d . . . . .
H25 H 0.465044 0.595116 -0.068044 0.067 Uiso 1 1 calc R U . . .
C26 C 0.7345(4) 0.5542(3) -0.09879(17) 0.0593(7) Uani 1 1 d . . . . .
H26 H 0.757867 0.470168 -0.117179 0.071 Uiso 1 1 calc R U . . .
C27 C 0.8767(4) 0.6034(3) -0.10179(17) 0.0581(7) Uani 1 1 d . . . . .
C28 C 0.8374(4) 0.7279(3) -0.07484(19) 0.0637(8) Uani 1 1 d . . . . .
H28 H 0.930523 0.762865 -0.077332 0.076 Uiso 1 1 calc R U . . .
C29 C 0.6621(4) 0.8033(3) -0.04393(18) 0.0594(7) Uani 1 1 d . . . . .
H29 H 0.638786 0.887535 -0.025948 0.071 Uiso 1 1 calc R U . . .
C30 C 1.0685(5) 0.5194(4) -0.1346(2) 0.0809(11) Uani 1 1 d . . . . .
H30A H 1.104324 0.432464 -0.101453 0.121 Uiso 1 1 calc R U . . .
H30B H 1.151578 0.564081 -0.128378 0.121 Uiso 1 1 calc R U . . .
H30C H 1.070939 0.508614 -0.194819 0.121 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 C21 1.777(2) . ?
S1 C24 1.779(3) . ?
O1 C1 1.375(3) . ?
O1 C2 1.374(3) . ?
O2 C1 1.205(3) . ?
O3 C14 1.362(3) . ?
O3 C17 1.419(3) . ?
N1 N2 1.360(3) . ?
N1 C3 1.369(3) . ?
N1 C18 1.438(3) . ?
N2 C10 1.347(3) . ?
C1 C5 1.472(3) . ?
C2 C3 1.368(3) . ?
C2 C10 1.409(3) . ?
C3 C4 1.438(4) . ?
C4 C5 1.418(3) . ?
C4 C9 1.396(3) . ?
C5 C6 1.398(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.453(3) . ?
C11 C12 1.397(3) . ?
C11 C16 1.395(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(4) . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.362(3) . ?
C18 C23 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(3) . ?
C21 C22 1.383(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(4) . ?
C24 C29 1.379(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.392(4) . ?
C27 C28 1.371(4) . ?
C27 C30 1.518(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.387(4) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C21 S1 C24 102.10(12) . . ?
C2 O1 C1 118.87(19) . . ?
C14 O3 C17 118.3(2) . . ?
N2 N1 C3 112.30(18) . . ?
N2 N1 C18 118.0(2) . . ?
C3 N1 C18 129.6(2) . . ?
C10 N2 N1 106.5(2) . . ?
O1 C1 C5 118.3(2) . . ?
O2 C1 O1 116.4(2) . . ?
O2 C1 C5 125.3(2) . . ?
O1 C2 C10 126.9(2) . . ?
C3 C2 O1 124.0(2) . . ?
C3 C2 C10 109.1(2) . . ?
N1 C3 C4 133.9(2) . . ?
C2 C3 N1 104.4(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 114.1(2) . . ?
C9 C4 C3 127.8(2) . . ?
C9 C4 C5 118.1(2) . . ?
C4 C5 C1 122.8(2) . . ?
C6 C5 C1 117.3(2) . . ?
C6 C5 C4 119.9(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.5(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
N2 C10 C2 107.7(2) . . ?
N2 C10 C11 122.4(2) . . ?
C2 C10 C11 129.9(2) . . ?
C12 C11 C10 121.3(2) . . ?
C16 C11 C10 121.6(2) . . ?
C16 C11 C12 117.1(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
O3 C14 C13 115.2(2) . . ?
O3 C14 C15 125.8(2) . . ?
C15 C14 C13 119.0(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.1 . . ?
C15 C16 C11 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N1 120.4(2) . . ?
C19 C18 C23 120.3(2) . . ?
C23 C18 N1 119.3(2) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 S1 124.04(18) . . ?
C22 C21 S1 117.0(2) . . ?
C22 C21 C20 118.9(2) . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.7(3) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 119.7(2) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 S1 120.0(2) . . ?
C29 C24 S1 120.7(2) . . ?
C29 C24 C25 119.3(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C30 119.8(3) . . ?
C28 C27 C26 118.1(3) . . ?
C28 C27 C30 122.0(3) . . ?
C27 C28 H28 119.2 . . ?
C27 C28 C29 121.7(3) . . ?
C29 C28 H28 119.2 . . ?
C24 C29 C28 119.8(3) . . ?
C24 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
S1 C21 C22 C23 -179.2(3) . . . . ?
S1 C24 C25 C26 -177.7(2) . . . . ?
S1 C24 C29 C28 178.3(2) . . . . ?
O1 C1 C5 C4 -0.5(3) . . . . ?
O1 C1 C5 C6 179.0(2) . . . . ?
O1 C2 C3 N1 178.6(2) . . . . ?
O1 C2 C3 C4 1.0(4) . . . . ?
O1 C2 C10 N2 -178.3(2) . . . . ?
O1 C2 C10 C11 1.8(4) . . . . ?
O2 C1 C5 C4 179.8(3) . . . . ?
O2 C1 C5 C6 -0.7(4) . . . . ?
O3 C14 C15 C16 179.9(2) . . . . ?
N1 N2 C10 C2 -0.2(3) . . . . ?
N1 N2 C10 C11 179.7(2) . . . . ?
N1 C3 C4 C5 -173.8(2) . . . . ?
N1 C3 C4 C9 5.2(4) . . . . ?
N1 C18 C19 C20 -178.0(2) . . . . ?
N1 C18 C23 C22 177.7(3) . . . . ?
N2 N1 C3 C2 -0.4(3) . . . . ?
N2 N1 C3 C4 176.7(2) . . . . ?
N2 N1 C18 C19 106.5(3) . . . . ?
N2 N1 C18 C23 -71.3(3) . . . . ?
N2 C10 C11 C12 167.7(2) . . . . ?
N2 C10 C11 C16 -12.7(4) . . . . ?
C1 O1 C2 C3 -4.9(3) . . . . ?
C1 O1 C2 C10 173.0(2) . . . . ?
C1 C5 C6 C7 -177.4(2) . . . . ?
C2 O1 C1 O2 -175.8(2) . . . . ?
C2 O1 C1 C5 4.5(3) . . . . ?
C2 C3 C4 C5 2.9(3) . . . . ?
C2 C3 C4 C9 -178.1(2) . . . . ?
C2 C10 C11 C12 -12.4(4) . . . . ?
C2 C10 C11 C16 167.2(3) . . . . ?
C3 N1 N2 C10 0.4(3) . . . . ?
C3 N1 C18 C19 -76.7(3) . . . . ?
C3 N1 C18 C23 105.5(3) . . . . ?
C3 C2 C10 N2 -0.1(3) . . . . ?
C3 C2 C10 C11 -180.0(2) . . . . ?
C3 C4 C5 C1 -3.1(3) . . . . ?
C3 C4 C5 C6 177.4(2) . . . . ?
C3 C4 C9 C8 -178.9(2) . . . . ?
C4 C5 C6 C7 2.1(4) . . . . ?
C5 C4 C9 C8 0.0(4) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C7 C8 C9 C4 1.2(4) . . . . ?
C9 C4 C5 C1 177.8(2) . . . . ?
C9 C4 C5 C6 -1.7(3) . . . . ?
C10 C2 C3 N1 0.3(3) . . . . ?
C10 C2 C3 C4 -177.2(2) . . . . ?
C10 C11 C12 C13 179.0(2) . . . . ?
C10 C11 C16 C15 -179.1(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C11 C16 C15 0.5(4) . . . . ?
C12 C13 C14 O3 -179.9(2) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C16 C11 C12 C13 -0.6(4) . . . . ?
C17 O3 C14 C13 173.8(3) . . . . ?
C17 O3 C14 C15 -7.0(4) . . . . ?
C18 N1 N2 C10 177.7(2) . . . . ?
C18 N1 C3 C2 -177.4(2) . . . . ?
C18 N1 C3 C4 -0.3(4) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C18 C23 C22 -0.1(5) . . . . ?
C19 C20 C21 S1 178.8(2) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C21 S1 C24 C25 91.4(2) . . . . ?
C21 S1 C24 C29 -88.3(2) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C23 C18 C19 C20 -0.2(4) . . . . ?
C24 S1 C21 C20 -3.6(3) . . . . ?
C24 S1 C21 C22 175.8(2) . . . . ?
C24 C25 C26 C27 -1.0(4) . . . . ?
C25 C24 C29 C28 -1.4(4) . . . . ?
C25 C26 C27 C28 -0.5(4) . . . . ?
C25 C26 C27 C30 179.7(3) . . . . ?
C26 C27 C28 C29 1.0(4) . . . . ?
C27 C28 C29 C24 -0.1(4) . . . . ?
C29 C24 C25 C26 2.0(4) . . . . ?
C30 C27 C28 C29 -179.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
