# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_k11202-myc-a_auto
_database_code_depnum_ccdc_archive 'CCDC 2349356'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2024-04-18 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;
_audit_creation_date             2023-02-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 N2 O2 S'
_chemical_formula_sum            'C23 H18 N2 O2 S'
_chemical_formula_weight         386.45
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   9.3268(5)
_cell_length_b                   15.1541(6)
_cell_length_c                   14.1675(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.462(6)
_cell_angle_gamma                90
_cell_volume                     1899.37(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8413
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8740
_cell_measurement_theta_min      2.0050
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12473
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.081
_diffrn_reflns_theta_min         2.025
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  41.00   0.50   18.01    --   10.60 -57.00 120.00  240
  2  ω    -15.00 100.00   0.50   18.01    --   10.60  77.00   0.00  230
  3  ω    -79.00  36.00   0.50   18.01    --   10.60 -77.00  30.00  230
  4  ω    -17.00 100.00   0.50   18.01    --   10.60  82.00 120.00  234
  5  ω    -79.00  36.00   0.50   18.01    --   10.60 -77.00 -90.00  230
  6  ω    -15.00 100.00   0.50   18.01    --   10.60  77.00-120.00  230
  7  ω   -100.00  14.00   0.50   18.01    --  -10.90 -82.00  60.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0164566000
_diffrn_orient_matrix_UB_12      0.0074674000
_diffrn_orient_matrix_UB_13      -0.0517585000
_diffrn_orient_matrix_UB_21      -0.0134408000
_diffrn_orient_matrix_UB_22      -0.0457634000
_diffrn_orient_matrix_UB_23      -0.0091026000
_diffrn_orient_matrix_UB_31      -0.0773371000
_diffrn_orient_matrix_UB_32      0.0063987000
_diffrn_orient_matrix_UB_33      -0.0047474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                3383
_reflns_number_total             3723
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.208
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1386 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.012
_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)+(0.0534P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0984
_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:
 C13(H13), C16(H16), C9(H9), C22(H22), C12(H12), C8(H8), C15(H15), C18(H18),
 C19(H19), C14(H14), C21(H21), C6(H6), C7(H7), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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 0.70253(8) 0.45849(5) 0.49092(5) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.8173(3) 0.39158(15) 0.50500(17) 0.0282(5) Uani 1 1 d . . . . .
O1 O 0.7428(3) 0.54991(13) 0.48792(18) 0.0287(6) Uani 1 1 d . . . . .
N2 N 0.4872(3) 0.44674(16) 0.7357(2) 0.0265(7) Uani 1 1 d . . . . .
N1 N 0.5007(3) 0.37182(16) 0.6888(2) 0.0269(6) Uani 1 1 d . . . . .
C2 C 0.5692(4) 0.37126(19) 0.6189(2) 0.0210(7) Uani 1 1 d . . . . .
C11 C 0.5225(4) 0.60164(19) 0.7705(2) 0.0207(7) Uani 1 1 d . . . . .
C13 C 0.3957(4) 0.6728(2) 0.8739(2) 0.0294(8) Uani 1 1 d . . . . .
H13 H 0.322403 0.671087 0.907552 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6062(4) 0.6780(2) 0.7736(2) 0.0259(7) Uani 1 1 d . . . . .
H16 H 0.677652 0.680373 0.738509 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5786(4) 0.28188(19) 0.5764(2) 0.0228(7) Uani 1 1 d . . . . .
C9 C 0.6099(4) 0.5273(2) 0.6383(2) 0.0207(7) Uani 1 1 d . . . . .
H9 H 0.645708 0.581793 0.621291 0.025 Uiso 1 1 calc R U . . .
C22 C 0.5433(4) 0.3520(2) 0.3372(2) 0.0262(7) Uani 1 1 d . . . . .
H22 H 0.617537 0.308060 0.364276 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4168(4) 0.5999(2) 0.8212(2) 0.0251(7) Uani 1 1 d . . . . .
H12 H 0.358577 0.548167 0.819521 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5532(4) 0.43459(19) 0.3822(2) 0.0213(7) Uani 1 1 d . . . . .
C8 C 0.7134(4) 0.2354(2) 0.6035(3) 0.0276(8) Uani 1 1 d . . . . .
H8 H 0.802351 0.261382 0.647389 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5863(4) 0.7510(2) 0.8276(3) 0.0292(8) Uani 1 1 d . . . . .
H15 H 0.644969 0.802709 0.830045 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4453(4) 0.4992(2) 0.3430(2) 0.0267(8) Uani 1 1 d . . . . .
H18 H 0.453092 0.555385 0.373877 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3267(4) 0.4805(2) 0.2583(3) 0.0299(8) Uani 1 1 d . . . . .
H19 H 0.252616 0.524493 0.231117 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4811(4) 0.7484(2) 0.8777(2) 0.0314(8) Uani 1 1 d . . . . .
H14 H 0.467293 0.798156 0.914694 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4231(4) 0.3354(2) 0.2520(2) 0.0289(8) Uani 1 1 d . . . . .
H21 H 0.415663 0.279659 0.220214 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5421(4) 0.5224(2) 0.7130(2) 0.0214(7) Uani 1 1 d . . . . .
C6 C 0.5896(5) 0.1138(2) 0.5015(3) 0.0344(9) Uani 1 1 d . . . . .
H6 H 0.593746 0.056517 0.475388 0.041 Uiso 1 1 calc R U . . .
C7 C 0.7187(4) 0.1513(2) 0.5668(2) 0.0307(8) Uani 1 1 d . . . . .
H7 H 0.810934 0.119237 0.586263 0.037 Uiso 1 1 calc R U . . .
C1 C 0.6230(4) 0.45057(18) 0.5904(2) 0.0204(7) Uani 1 1 d . . . . .
C20 C 0.3130(4) 0.3991(2) 0.2122(2) 0.0285(8) Uani 1 1 d . . . . .
C4 C 0.4494(4) 0.2437(2) 0.5130(3) 0.0311(8) Uani 1 1 d . . . . .
H4 H 0.356256 0.274851 0.495535 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4554(5) 0.1598(2) 0.4747(3) 0.0381(9) Uani 1 1 d . . . . .
H5 H 0.366797 0.134200 0.430065 0.046 Uiso 1 1 calc R U . . .
C23 C 0.1815(5) 0.3786(3) 0.1208(3) 0.0450(10) Uani 1 1 d . . . . .
H23A H 0.097269 0.418305 0.117937 0.068 Uiso 1 1 calc R U . . .
H23B H 0.149674 0.317343 0.123736 0.068 Uiso 1 1 calc R U . . .
H23C H 0.212125 0.386969 0.061308 0.068 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 O2 1.441(2) . ?
S1 O1 1.440(2) . ?
S1 C17 1.756(3) . ?
S1 C1 1.792(3) . ?
N2 N1 1.341(3) . ?
N2 C10 1.335(4) . ?
N1 C2 1.338(4) . ?
C2 C3 1.496(4) . ?
C2 C1 1.411(4) . ?
C11 C16 1.388(4) . ?
C11 C12 1.392(4) . ?
C11 C10 1.494(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.381(4) . ?
C13 C14 1.386(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.391(4) . ?
C3 C8 1.385(5) . ?
C3 C4 1.381(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(4) . ?
C9 C1 1.371(4) . ?
C22 H22 0.9500 . ?
C22 C17 1.394(4) . ?
C22 C21 1.386(5) . ?
C12 H12 0.9500 . ?
C17 C18 1.387(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.384(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.382(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(5) . ?
C14 H14 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.391(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(5) . ?
C6 C5 1.377(5) . ?
C7 H7 0.9500 . ?
C20 C23 1.507(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(5) . ?
C5 H5 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
O2 S1 C17 108.92(14) . . ?
O2 S1 C1 108.54(14) . . ?
O1 S1 O2 119.45(14) . . ?
O1 S1 C17 108.33(14) . . ?
O1 S1 C1 105.34(13) . . ?
C17 S1 C1 105.36(15) . . ?
C10 N2 N1 120.3(3) . . ?
C2 N1 N2 120.9(3) . . ?
N1 C2 C3 114.0(3) . . ?
N1 C2 C1 120.3(3) . . ?
C1 C2 C3 125.7(3) . . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 C10 121.5(3) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C11 C16 H16 119.7 . . ?
C11 C16 C15 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C8 C3 C2 120.8(3) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 C8 119.7(3) . . ?
C10 C9 H9 121.2 . . ?
C1 C9 H9 121.2 . . ?
C1 C9 C10 117.6(3) . . ?
C17 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C21 C22 C17 118.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C22 C17 S1 120.4(3) . . ?
C18 C17 S1 118.6(2) . . ?
C18 C17 C22 121.0(3) . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.5(3) . . ?
C20 C19 H19 119.2 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C22 C21 H21 119.4 . . ?
C22 C21 C20 121.1(3) . . ?
C20 C21 H21 119.4 . . ?
N2 C10 C11 115.9(3) . . ?
N2 C10 C9 121.9(3) . . ?
C9 C10 C11 122.2(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C1 S1 123.8(2) . . ?
C9 C1 S1 117.2(2) . . ?
C9 C1 C2 119.0(3) . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 C23 121.2(3) . . ?
C21 C20 C23 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 C17 C18 C19 -179.2(2) . . . . ?
O2 S1 C17 C22 13.6(3) . . . . ?
O2 S1 C17 C18 -166.9(2) . . . . ?
O2 S1 C1 C2 -50.6(3) . . . . ?
O2 S1 C1 C9 131.7(3) . . . . ?
O1 S1 C17 C22 145.0(2) . . . . ?
O1 S1 C17 C18 -35.5(3) . . . . ?
O1 S1 C1 C2 -179.7(3) . . . . ?
O1 S1 C1 C9 2.7(3) . . . . ?
N2 N1 C2 C3 178.2(3) . . . . ?
N2 N1 C2 C1 -2.7(5) . . . . ?
N1 N2 C10 C11 -179.3(3) . . . . ?
N1 N2 C10 C9 2.3(5) . . . . ?
N1 C2 C3 C8 -104.4(4) . . . . ?
N1 C2 C3 C4 72.6(4) . . . . ?
N1 C2 C1 S1 -174.8(2) . . . . ?
N1 C2 C1 C9 2.8(5) . . . . ?
C2 C3 C8 C7 177.3(3) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C11 C16 C15 C14 -0.8(5) . . . . ?
C16 C11 C12 C13 -0.2(5) . . . . ?
C16 C11 C10 N2 163.1(3) . . . . ?
C16 C11 C10 C9 -18.6(5) . . . . ?
C16 C15 C14 C13 0.0(5) . . . . ?
C3 C2 C1 S1 4.2(5) . . . . ?
C3 C2 C1 C9 -178.2(3) . . . . ?
C3 C8 C7 C6 1.0(5) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C22 C17 C18 C19 0.3(5) . . . . ?
C22 C21 C20 C19 1.1(5) . . . . ?
C22 C21 C20 C23 -178.7(3) . . . . ?
C12 C11 C16 C15 0.9(5) . . . . ?
C12 C11 C10 N2 -17.8(5) . . . . ?
C12 C11 C10 C9 160.6(3) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C17 S1 C1 C2 65.9(3) . . . . ?
C17 S1 C1 C9 -111.7(3) . . . . ?
C17 C22 C21 C20 -0.6(5) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C8 C3 C4 C5 -1.5(5) . . . . ?
C18 C19 C20 C21 -0.8(5) . . . . ?
C18 C19 C20 C23 178.9(3) . . . . ?
C14 C13 C12 C11 -0.7(5) . . . . ?
C21 C22 C17 S1 179.4(2) . . . . ?
C21 C22 C17 C18 -0.1(4) . . . . ?
C10 N2 N1 C2 0.1(5) . . . . ?
C10 C11 C16 C15 -179.9(3) . . . . ?
C10 C11 C12 C13 -179.3(3) . . . . ?
C10 C9 C1 S1 177.3(2) . . . . ?
C10 C9 C1 C2 -0.5(5) . . . . ?
C7 C6 C5 C4 0.0(5) . . . . ?
C1 S1 C17 C22 -102.7(3) . . . . ?
C1 S1 C17 C18 76.8(3) . . . . ?
C1 C2 C3 C8 76.6(4) . . . . ?
C1 C2 C3 C4 -106.4(4) . . . . ?
C1 C9 C10 N2 -2.1(5) . . . . ?
C1 C9 C10 C11 179.7(3) . . . . ?
C4 C3 C8 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -1.2(5) . . . . ?

_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 5.139
_oxdiff_exptl_absorpt_empirical_full_min 0.282
####################################################################### 
# 
# 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_k11204-myc-c_auto
_database_code_depnum_ccdc_archive 'CCDC 2349357'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2024-04-18 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H20 N2 O2 S'
_chemical_formula_sum            'C28 H22 N2 O2 S'
_chemical_formula_weight         450.53
_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                   9.3979(2)
_cell_length_b                   11.3031(3)
_cell_length_c                   12.3737(3)
_cell_angle_alpha                114.887(3)
_cell_angle_beta                 109.317(2)
_cell_angle_gamma                92.845(2)
_cell_volume                     1097.50(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16279
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8630
_cell_measurement_theta_min      1.9670
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27690
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_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    -79.00  37.00   0.50    2.44    --   10.60 -60.00-150.00  232
  2  ω    -16.00 100.00   0.50    2.44    --   10.60  60.00 -11.00  232
  3  ω   -100.00  15.00   0.50    2.44    --  -10.90 -60.00-150.00  230
  4  ω    -17.00 100.00   0.50    2.44    --   10.60  82.00  90.00  234
  5  ω    -17.00 100.00   0.50    2.44    --   10.60  82.00-150.00  234
  6  ω    -79.00  36.00   0.50    2.44    --   10.60 -77.00   0.00  230
  7  ω    -17.00 100.00   0.50    2.44    --   10.60  82.00  60.00  234
  8  ω    -17.00 100.00   0.50    2.44    --   10.60  82.00   0.00  234
  9  ω    -17.00 100.00   0.50    2.44    --   10.60  82.00-180.00  234
 10  ω    -17.00 100.00   0.50    2.44    --   10.60  82.00 -90.00  234
 11  ω    -79.00  41.00   0.50    2.44    --   10.60 -57.00 120.00  240
 12  ω    -79.00  36.00   0.50    2.44    --   10.60 -77.00 -30.00  230
 13  ω    -15.00  90.00   0.50    2.44    --   10.60  77.00 120.00  210
 14  ω     -7.00  18.00   0.50    2.44    --   10.60  82.00-120.00   50
 15  ω     -4.00  21.00   0.50    2.44    --  -10.90  60.00 -11.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0191377000
_diffrn_orient_matrix_UB_12      0.0652855000
_diffrn_orient_matrix_UB_13      0.0075776000
_diffrn_orient_matrix_UB_21      0.0313296000
_diffrn_orient_matrix_UB_22      -0.0253158000
_diffrn_orient_matrix_UB_23      -0.0480536000
_diffrn_orient_matrix_UB_31      -0.0733189000
_diffrn_orient_matrix_UB_32      -0.0112738000
_diffrn_orient_matrix_UB_33      -0.0483205000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3375
_reflns_number_total             3861
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.336
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.081
_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)+(0.0420P)²+0.4121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0898
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C2(H2), C5(H5), C6(H6), C7(H7), C21(H21), C19(H19),
 C24(H24), C12(H12), C16(H16), C25(H25), C28(H28), C9(H9), C15(H15), C26(H26),
 C27(H27), C8(H8), C14(H14), C13(H13)
;
_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 0.44376(4) 0.71864(4) 0.96980(4) 0.01963(12) Uani 1 1 d . . . . .
O1 O 0.53431(12) 0.64757(11) 1.02910(11) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.43267(13) 0.85056(10) 1.05063(10) 0.0258(3) Uani 1 1 d . . . . .
N1 N -0.00529(15) 0.55136(12) 0.72245(13) 0.0221(3) Uani 1 1 d . . . . .
N2 N -0.03951(15) 0.45507(13) 0.75183(13) 0.0222(3) Uani 1 1 d . . . . .
C10 C 0.13492(17) 0.63326(15) 0.78519(15) 0.0198(3) Uani 1 1 d . . . . .
C18 C 0.54120(17) 0.61055(15) 0.76913(15) 0.0210(3) Uani 1 1 d . . . . .
H18 H 0.532877 0.530108 0.776005 0.025 Uiso 1 1 calc R U . . .
C3 C 0.06720(17) 0.43695(15) 0.84287(15) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.15627(17) 0.73167(15) 0.73808(15) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.25104(17) 0.61666(14) 0.88114(15) 0.0186(3) Uani 1 1 d . . . . .
C22 C 0.52369(17) 0.84292(15) 0.84596(15) 0.0213(3) Uani 1 1 d . . . . .
H22 H 0.505802 0.920681 0.906193 0.026 Uiso 1 1 calc R U . . .
C23 C 0.62721(17) 0.73850(15) 0.55424(15) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.50850(17) 0.72416(15) 0.85340(15) 0.0191(3) Uani 1 1 d . . . . .
C20 C 0.59415(17) 0.73436(15) 0.66223(15) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.21753(17) 0.51672(14) 0.90970(15) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.293726 0.501896 0.972793 0.023 Uiso 1 1 calc R U . . .
C5 C 0.09223(18) 0.32376(15) 0.98245(15) 0.0222(3) Uani 1 1 d . . . . .
H5 H 0.173226 0.396975 1.050890 0.027 Uiso 1 1 calc R U . . .
C4 C 0.01980(18) 0.32451(15) 0.86491(15) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.04725(19) 0.21706(16) 1.00060(16) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.096565 0.218136 1.081659 0.030 Uiso 1 1 calc R U . . .
C7 C -0.0688(2) 0.10945(17) 0.90146(17) 0.0289(4) Uani 1 1 d . . . . .
H7 H -0.099090 0.036292 0.913976 0.035 Uiso 1 1 calc R U . . .
C21 C 0.56496(18) 0.84705(15) 0.75041(15) 0.0221(3) Uani 1 1 d . . . . .
H21 H 0.573726 0.927954 0.744396 0.027 Uiso 1 1 calc R U . . .
C19 C 0.58582(17) 0.61722(15) 0.67573(15) 0.0213(3) Uani 1 1 d . . . . .
H19 H 0.611276 0.541356 0.619740 0.026 Uiso 1 1 calc R U . . .
C24 C 0.74567(18) 0.68476(15) 0.52103(15) 0.0241(4) Uani 1 1 d . . . . .
H24 H 0.807174 0.644494 0.567790 0.029 Uiso 1 1 calc R U . . .
C12 C 0.17004(19) 0.86765(16) 0.81106(17) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.168766 0.901066 0.895114 0.031 Uiso 1 1 calc R U . . .
C16 C 0.15873(18) 0.68364(16) 0.61502(16) 0.0246(4) Uani 1 1 d . . . . .
H16 H 0.147918 0.590604 0.564125 0.030 Uiso 1 1 calc R U . . .
C25 C 0.77417(19) 0.68983(16) 0.41979(16) 0.0276(4) Uani 1 1 d . . . . .
H25 H 0.856240 0.654047 0.398622 0.033 Uiso 1 1 calc R U . . .
C28 C 0.53840(19) 0.79657(17) 0.48357(17) 0.0283(4) Uani 1 1 d . . . . .
H28 H 0.458058 0.834787 0.505851 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0978(2) 0.21529(17) 0.76593(17) 0.0320(4) Uani 1 1 d . . . . .
H9 H -0.148958 0.214294 0.685149 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1769(2) 0.77130(17) 0.56702(17) 0.0306(4) Uani 1 1 d . . . . .
H15 H 0.180710 0.738598 0.483858 0.037 Uiso 1 1 calc R U . . .
C26 C 0.6849(2) 0.74618(17) 0.34947(16) 0.0297(4) Uani 1 1 d . . . . .
H26 H 0.704716 0.748620 0.279893 0.036 Uiso 1 1 calc R U . . .
C27 C 0.5662(2) 0.79911(18) 0.38114(18) 0.0332(4) Uani 1 1 d . . . . .
H27 H 0.503520 0.837272 0.332623 0.040 Uiso 1 1 calc R U . . .
C8 C -0.1407(2) 0.10835(18) 0.78394(18) 0.0350(4) Uani 1 1 d . . . . .
H8 H -0.219993 0.033906 0.715240 0.042 Uiso 1 1 calc R U . . .
C14 C 0.1896(2) 0.90661(18) 0.63976(18) 0.0329(4) Uani 1 1 d . . . . .
H14 H 0.200918 0.966427 0.606027 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1857(2) 0.95481(17) 0.76123(18) 0.0309(4) Uani 1 1 d . . . . .
H13 H 0.193734 1.047645 0.810755 0.037 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 O1 1.4348(11) . ?
S1 O2 1.4367(11) . ?
S1 C1 1.7963(16) . ?
S1 C17 1.7607(15) . ?
N1 N2 1.3402(17) . ?
N1 C10 1.339(2) . ?
N2 C3 1.336(2) . ?
C10 C11 1.489(2) . ?
C10 C1 1.409(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.398(2) . ?
C18 C19 1.381(2) . ?
C3 C2 1.402(2) . ?
C3 C4 1.485(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.394(2) . ?
C1 C2 1.369(2) . ?
C22 H22 0.9500 . ?
C22 C17 1.387(2) . ?
C22 C21 1.378(2) . ?
C23 C20 1.487(2) . ?
C23 C24 1.392(2) . ?
C23 C28 1.395(2) . ?
C20 C21 1.397(2) . ?
C20 C19 1.404(2) . ?
C2 H2 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.391(2) . ?
C5 C6 1.387(2) . ?
C4 C9 1.393(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(2) . ?
C21 H21 0.9500 . ?
C19 H19 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.382(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.380(2) . ?
C28 H28 0.9500 . ?
C28 C27 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.384(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.384(2) . ?
C27 H27 0.9500 . ?
C8 H8 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.381(3) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.97(7) . . ?
O1 S1 C1 106.00(7) . . ?
O1 S1 C17 108.85(7) . . ?
O2 S1 C1 107.22(7) . . ?
O2 S1 C17 109.13(7) . . ?
C17 S1 C1 105.88(7) . . ?
C10 N1 N2 121.03(13) . . ?
C3 N2 N1 120.46(13) . . ?
N1 C10 C11 114.46(13) . . ?
N1 C10 C1 120.19(13) . . ?
C1 C10 C11 125.21(14) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C19 C18 C17 118.90(13) . . ?
N2 C3 C2 121.42(13) . . ?
N2 C3 C4 116.38(13) . . ?
C2 C3 C4 122.15(14) . . ?
C12 C11 C10 122.32(14) . . ?
C12 C11 C16 119.56(14) . . ?
C16 C11 C10 118.10(14) . . ?
C10 C1 S1 124.14(11) . . ?
C2 C1 S1 116.90(12) . . ?
C2 C1 C10 118.97(14) . . ?
C17 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C17 119.39(14) . . ?
C24 C23 C20 121.28(14) . . ?
C24 C23 C28 118.66(14) . . ?
C28 C23 C20 120.06(14) . . ?
C18 C17 S1 120.56(11) . . ?
C22 C17 S1 118.48(12) . . ?
C22 C17 C18 120.95(14) . . ?
C21 C20 C23 120.09(13) . . ?
C21 C20 C19 118.44(14) . . ?
C19 C20 C23 121.43(13) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 C3 117.89(14) . . ?
C1 C2 H2 121.1 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.58(15) . . ?
C5 C4 C3 121.49(14) . . ?
C5 C4 C9 118.45(14) . . ?
C9 C4 C3 120.05(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.25(15) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.78(15) . . ?
C8 C7 H7 120.1 . . ?
C22 C21 C20 121.16(14) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C18 C19 C20 121.04(14) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.17(15) . . ?
C25 C24 H24 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.04(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.03(15) . . ?
C15 C16 H16 120.0 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.85(15) . . ?
C26 C25 H25 119.6 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.70(15) . . ?
C27 C28 H28 119.6 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.75(16) . . ?
C8 C9 H9 119.6 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.20(16) . . ?
C14 C15 H15 119.9 . . ?
C25 C26 H26 120.3 . . ?
C25 C26 C27 119.44(15) . . ?
C27 C26 H26 120.3 . . ?
C28 C27 H27 119.9 . . ?
C26 C27 C28 120.16(16) . . ?
C26 C27 H27 119.9 . . ?
C7 C8 C9 120.19(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.12(15) . . ?
C13 C14 H14 119.9 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.04(16) . . ?
C14 C13 H13 120.0 . . ?

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 179.19(11) . . . . ?
O1 S1 C1 C10 -164.36(12) . . . . ?
O1 S1 C1 C2 15.33(13) . . . . ?
O1 S1 C17 C18 43.44(14) . . . . ?
O1 S1 C17 C22 -137.62(12) . . . . ?
O2 S1 C1 C10 67.59(14) . . . . ?
O2 S1 C1 C2 -112.72(12) . . . . ?
O2 S1 C17 C18 174.75(12) . . . . ?
O2 S1 C17 C22 -6.31(15) . . . . ?
N1 N2 C3 C2 -0.4(2) . . . . ?
N1 N2 C3 C4 -177.78(13) . . . . ?
N1 C10 C11 C12 110.26(17) . . . . ?
N1 C10 C11 C16 -68.25(18) . . . . ?
N1 C10 C1 S1 179.05(11) . . . . ?
N1 C10 C1 C2 -0.6(2) . . . . ?
N2 N1 C10 C11 177.96(13) . . . . ?
N2 N1 C10 C1 2.0(2) . . . . ?
N2 C3 C2 C1 1.6(2) . . . . ?
N2 C3 C4 C5 -155.58(14) . . . . ?
N2 C3 C4 C9 25.6(2) . . . . ?
C10 N1 N2 C3 -1.5(2) . . . . ?
C10 C11 C12 C13 -178.30(15) . . . . ?
C10 C11 C16 C15 179.43(15) . . . . ?
C10 C1 C2 C3 -1.1(2) . . . . ?
C3 C4 C9 C8 178.46(16) . . . . ?
C11 C10 C1 S1 3.5(2) . . . . ?
C11 C10 C1 C2 -176.18(14) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C11 C16 C15 C14 -1.3(2) . . . . ?
C1 S1 C17 C18 -70.13(14) . . . . ?
C1 S1 C17 C22 108.81(13) . . . . ?
C1 C10 C11 C12 -74.0(2) . . . . ?
C1 C10 C11 C16 107.51(18) . . . . ?
C23 C20 C21 C22 175.52(14) . . . . ?
C23 C20 C19 C18 -174.01(14) . . . . ?
C23 C24 C25 C26 -0.9(2) . . . . ?
C23 C28 C27 C26 -1.3(3) . . . . ?
C17 S1 C1 C10 -48.83(14) . . . . ?
C17 S1 C1 C2 130.86(12) . . . . ?
C17 C18 C19 C20 -1.9(2) . . . . ?
C17 C22 C21 C20 -1.0(2) . . . . ?
C20 C23 C24 C25 179.98(14) . . . . ?
C20 C23 C28 C27 -178.88(15) . . . . ?
C2 C3 C4 C5 27.0(2) . . . . ?
C2 C3 C4 C9 -151.75(16) . . . . ?
C5 C4 C9 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C4 C3 C2 C1 178.88(13) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C4 C9 C8 C7 0.9(3) . . . . ?
C6 C5 C4 C3 -179.33(14) . . . . ?
C6 C5 C4 C9 -0.5(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C21 C22 C17 S1 -176.02(12) . . . . ?
C21 C22 C17 C18 2.9(2) . . . . ?
C21 C20 C19 C18 3.7(2) . . . . ?
C19 C18 C17 S1 177.45(11) . . . . ?
C19 C18 C17 C22 -1.5(2) . . . . ?
C19 C20 C21 C22 -2.2(2) . . . . ?
C24 C23 C20 C21 136.34(16) . . . . ?
C24 C23 C20 C19 -46.0(2) . . . . ?
C24 C23 C28 C27 0.9(2) . . . . ?
C24 C25 C26 C27 0.5(3) . . . . ?
C12 C11 C16 C15 0.9(2) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C16 C15 C14 C13 0.7(3) . . . . ?
C25 C26 C27 C28 0.6(3) . . . . ?
C28 C23 C20 C21 -43.9(2) . . . . ?
C28 C23 C20 C19 133.74(16) . . . . ?
C28 C23 C24 C25 0.2(2) . . . . ?
C15 C14 C13 C12 0.4(3) . . . . ?

_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 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.679
####################################################################### 
# 
# 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_k11112-myc-c(oy4143)_auto
_database_code_depnum_ccdc_archive 'CCDC 2349359'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2024-04-18 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;
_audit_creation_date             2022-12-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 N4 O'
_chemical_formula_sum            'C24 H18 N4 O'
_chemical_formula_weight         378.42
_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'

_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                   11.1986(2)
_cell_length_b                   7.45530(10)
_cell_length_c                   21.8767(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.888(2)
_cell_angle_gamma                90
_cell_volume                     1824.14(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17981
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.0240
_cell_measurement_theta_min      1.8800
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.993
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00 100.00   0.50    3.13    --   10.60  77.00  30.00  230
  2  ω    -79.00 100.00   0.50    3.13    --   10.60   0.00 150.00  358
  3  ω    -17.00 100.00   0.50    3.13    --   10.60  82.00  60.00  234
  4  ω    -17.00 100.00   0.50    3.13    --   10.60  82.00   0.00  234
  5  ω    -27.00 100.00   0.50    3.13    --   10.60  37.00 -60.00  254
  6  ω    -17.00 100.00   0.50    3.13    --   10.60  82.00  90.00  234
  7  ω    -15.00 100.00   0.50    3.13    --   10.60  77.00 -90.00  230
  8  ω    -36.00  78.00   0.50    3.13    --  -10.90  63.00 -49.38  228
  9  ω    -79.00  41.00   0.50    3.13    --   10.60 -57.00  60.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0019018000
_diffrn_orient_matrix_UB_12      0.0925672000
_diffrn_orient_matrix_UB_13      -0.0074512000
_diffrn_orient_matrix_UB_21      0.0195504000
_diffrn_orient_matrix_UB_22      -0.0198438000
_diffrn_orient_matrix_UB_23      -0.0295873000
_diffrn_orient_matrix_UB_31      -0.0603175000
_diffrn_orient_matrix_UB_32      -0.0093923000
_diffrn_orient_matrix_UB_33      -0.0110697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3366
_reflns_number_total             3873
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.288
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0079(11)
_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   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.097
_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)+(0.0459P)²+0.3581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0997
_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), C2(H2), C7(H7), C14(H14), C18(H18), C15(H15), C10(H10), C17(H17),
 C16(H16), C9(H9), C21(H21), C20(H20), C24(H24), C22(H22), C23(H23)
2.b 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
O1 O 0.97433(8) 0.55327(13) 0.30493(4) 0.0349(2) Uani 1 1 d . . . . .
N3 N 0.49646(8) 0.22677(12) 0.53054(4) 0.0214(2) Uani 1 1 d . . . . .
N1 N 0.72518(9) 0.34286(13) 0.54897(4) 0.0255(2) Uani 1 1 d . . . . .
N4 N 0.38350(8) 0.17284(13) 0.51554(4) 0.0234(2) Uani 1 1 d . . . . .
N2 N 0.65979(9) 0.28814(14) 0.59729(4) 0.0254(2) Uani 1 1 d . . . . .
C3 C 0.55476(10) 0.29262(15) 0.48069(5) 0.0214(2) Uani 1 1 d . . . . .
C5 C 0.75340(10) 0.40376(15) 0.44354(5) 0.0232(3) Uani 1 1 d . . . . .
C12 C 0.55064(10) 0.22805(15) 0.58853(5) 0.0222(2) Uani 1 1 d . . . . .
C6 C 0.85251(11) 0.51187(16) 0.45727(5) 0.0250(3) Uani 1 1 d . . . . .
H6 H 0.868404 0.549957 0.498313 0.030 Uiso 1 1 calc R U . . .
C4 C 0.67652(10) 0.34514(15) 0.49283(5) 0.0226(2) Uani 1 1 d . . . . .
C19 C 0.25298(10) 0.17046(16) 0.42327(5) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.36885(10) 0.20874(15) 0.45548(5) 0.0225(2) Uani 1 1 d . . . . .
C13 C 0.48823(10) 0.15765(15) 0.64162(5) 0.0225(3) Uani 1 1 d . . . . .
C8 C 0.90510(11) 0.51093(17) 0.35241(5) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.47194(10) 0.28347(15) 0.43194(5) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.482501 0.320116 0.390976 0.028 Uiso 1 1 calc R U . . .
C7 C 0.92864(11) 0.56549(16) 0.41269(5) 0.0264(3) Uani 1 1 d . . . . .
H7 H 0.996081 0.638606 0.423142 0.032 Uiso 1 1 calc R U . . .
C14 C 0.36487(11) 0.16941(16) 0.64733(5) 0.0253(3) Uani 1 1 d . . . . .
H14 H 0.315825 0.225057 0.616106 0.030 Uiso 1 1 calc R U . . .
C18 C 0.55908(11) 0.07783(16) 0.68863(5) 0.0263(3) Uani 1 1 d . . . . .
H18 H 0.643381 0.072678 0.685782 0.032 Uiso 1 1 calc R U . . .
C15 C 0.31406(11) 0.09931(17) 0.69891(5) 0.0283(3) Uani 1 1 d . . . . .
H15 H 0.230272 0.109036 0.703045 0.034 Uiso 1 1 calc R U . . .
C10 C 0.73196(11) 0.34952(17) 0.38252(5) 0.0275(3) Uani 1 1 d . . . . .
H10 H 0.665680 0.274123 0.372024 0.033 Uiso 1 1 calc R U . . .
C17 C 0.50694(12) 0.00634(17) 0.73926(5) 0.0300(3) Uani 1 1 d . . . . .
H17 H 0.555519 -0.049227 0.770687 0.036 Uiso 1 1 calc R U . . .
C16 C 0.38443(12) 0.01545(17) 0.74432(5) 0.0298(3) Uani 1 1 d . . . . .
H16 H 0.348733 -0.035551 0.778760 0.036 Uiso 1 1 calc R U . . .
C9 C 0.80597(11) 0.40442(18) 0.33767(5) 0.0299(3) Uani 1 1 d . . . . .
H9 H 0.789106 0.369213 0.296403 0.036 Uiso 1 1 calc R U . . .
C21 C 0.12455(12) 0.18144(18) 0.33159(6) 0.0353(3) Uani 1 1 d . . . . .
H21 H 0.112502 0.212038 0.289580 0.042 Uiso 1 1 calc R U . . .
C20 C 0.23327(11) 0.21642(17) 0.36208(5) 0.0300(3) Uani 1 1 d . . . . .
H20 H 0.295174 0.272528 0.340904 0.036 Uiso 1 1 calc R U . . .
C24 C 0.16153(12) 0.08787(18) 0.45346(6) 0.0328(3) Uani 1 1 d . . . . .
H24 H 0.174115 0.053411 0.495089 0.039 Uiso 1 1 calc R U . . .
C11 C 1.08589(12) 0.64131(19) 0.31913(6) 0.0357(3) Uani 1 1 d . . . . .
H11A H 1.130918 0.650862 0.282001 0.054 Uiso 1 1 calc R U . . .
H11B H 1.132256 0.571739 0.350034 0.054 Uiso 1 1 calc R U . . .
H11C H 1.070861 0.761619 0.335077 0.054 Uiso 1 1 calc R U . . .
C22 C 0.03354(12) 0.10208(18) 0.36220(6) 0.0369(3) Uani 1 1 d . . . . .
H22 H -0.041553 0.079523 0.341476 0.044 Uiso 1 1 calc R U . . .
C23 C 0.05206(12) 0.0556(2) 0.42305(6) 0.0390(3) Uani 1 1 d . . . . .
H23 H -0.010561 0.001216 0.444177 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
O1 C8 1.3642(13) . ?
O1 C11 1.4314(16) . ?
N3 N4 1.3520(13) . ?
N3 C3 1.3886(14) . ?
N3 C12 1.3784(14) . ?
N1 N2 1.3776(13) . ?
N1 C4 1.3185(14) . ?
N4 C1 1.3429(14) . ?
N2 C12 1.3069(15) . ?
C3 C4 1.4306(16) . ?
C3 C2 1.3794(16) . ?
C5 C6 1.3921(17) . ?
C5 C4 1.4792(15) . ?
C5 C10 1.4040(16) . ?
C12 C13 1.4813(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3861(16) . ?
C19 C1 1.4729(16) . ?
C19 C20 1.3888(16) . ?
C19 C24 1.3899(17) . ?
C1 C2 1.4029(16) . ?
C13 C14 1.3960(16) . ?
C13 C18 1.3997(16) . ?
C8 C7 1.3923(16) . ?
C8 C9 1.3896(18) . ?
C2 H2 0.9500 . ?
C7 H7 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.3910(16) . ?
C18 H18 0.9500 . ?
C18 C17 1.3846(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3856(18) . ?
C10 H10 0.9500 . ?
C10 C9 1.3780(16) . ?
C17 H17 0.9500 . ?
C17 C16 1.3835(18) . ?
C16 H16 0.9500 . ?
C9 H9 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.3832(17) . ?
C21 C22 1.380(2) . ?
C20 H20 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.3860(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.381(2) . ?
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
C8 O1 C11 117.65(9) . . ?
N4 N3 C3 112.68(9) . . ?
N4 N3 C12 126.05(9) . . ?
C12 N3 C3 121.19(10) . . ?
C4 N1 N2 120.53(10) . . ?
C1 N4 N3 104.18(9) . . ?
C12 N2 N1 121.23(9) . . ?
N3 C3 C4 115.62(10) . . ?
C2 C3 N3 105.39(10) . . ?
C2 C3 C4 138.98(10) . . ?
C6 C5 C4 120.06(10) . . ?
C6 C5 C10 117.91(10) . . ?
C10 C5 C4 122.01(11) . . ?
N3 C12 C13 121.05(10) . . ?
N2 C12 N3 120.16(10) . . ?
N2 C12 C13 118.77(10) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.81(10) . . ?
C7 C6 H6 119.1 . . ?
N1 C4 C3 120.97(10) . . ?
N1 C4 C5 117.03(10) . . ?
C3 C4 C5 122.00(10) . . ?
C20 C19 C1 120.44(11) . . ?
C20 C19 C24 118.82(11) . . ?
C24 C19 C1 120.73(10) . . ?
N4 C1 C19 119.38(10) . . ?
N4 C1 C2 112.09(10) . . ?
C2 C1 C19 128.52(10) . . ?
C14 C13 C12 123.78(10) . . ?
C14 C13 C18 119.20(10) . . ?
C18 C13 C12 117.02(10) . . ?
O1 C8 C7 124.47(11) . . ?
O1 C8 C9 115.69(10) . . ?
C9 C8 C7 119.84(10) . . ?
C3 C2 C1 105.64(10) . . ?
C3 C2 H2 127.2 . . ?
C1 C2 H2 127.2 . . ?
C6 C7 C8 119.23(11) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.74(11) . . ?
C15 C14 H14 120.1 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.34(11) . . ?
C17 C18 H18 119.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.67(11) . . ?
C16 C15 H15 119.7 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.75(11) . . ?
C9 C10 H10 119.6 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 C18 120.32(11) . . ?
C16 C17 H17 119.8 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.69(11) . . ?
C17 C16 H16 120.2 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.44(11) . . ?
C10 C9 H9 119.8 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.03(12) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.77(12) . . ?
C21 C20 H20 119.6 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.26(12) . . ?
C23 C24 H24 119.9 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.75(12) . . ?
C23 C22 H22 120.1 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.35(13) . . ?
C22 C23 H23 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
O1 C8 C7 C6 -179.11(11) . . . . ?
O1 C8 C9 C10 178.12(11) . . . . ?
N3 N4 C1 C19 -178.59(9) . . . . ?
N3 N4 C1 C2 0.59(12) . . . . ?
N3 C3 C4 N1 -4.99(16) . . . . ?
N3 C3 C4 C5 174.90(10) . . . . ?
N3 C3 C2 C1 -1.14(12) . . . . ?
N3 C12 C13 C14 -33.23(16) . . . . ?
N3 C12 C13 C18 147.81(11) . . . . ?
N1 N2 C12 N3 -3.26(17) . . . . ?
N1 N2 C12 C13 175.18(9) . . . . ?
N4 N3 C3 C4 -177.48(9) . . . . ?
N4 N3 C3 C2 1.62(12) . . . . ?
N4 N3 C12 N2 -178.17(10) . . . . ?
N4 N3 C12 C13 3.42(16) . . . . ?
N4 C1 C2 C3 0.37(13) . . . . ?
N2 N1 C4 C3 0.56(16) . . . . ?
N2 N1 C4 C5 -179.33(10) . . . . ?
N2 C12 C13 C14 148.35(12) . . . . ?
N2 C12 C13 C18 -30.61(16) . . . . ?
C3 N3 N4 C1 -1.37(12) . . . . ?
C3 N3 C12 N2 -1.57(16) . . . . ?
C3 N3 C12 C13 -179.97(10) . . . . ?
C5 C6 C7 C8 0.45(18) . . . . ?
C5 C10 C9 C8 1.66(19) . . . . ?
C12 N3 N4 C1 175.48(10) . . . . ?
C12 N3 C3 C4 5.50(15) . . . . ?
C12 N3 C3 C2 -175.41(10) . . . . ?
C12 C13 C14 C15 179.99(11) . . . . ?
C12 C13 C18 C17 -178.95(10) . . . . ?
C6 C5 C4 N1 -23.22(16) . . . . ?
C6 C5 C4 C3 156.90(11) . . . . ?
C6 C5 C10 C9 -1.01(18) . . . . ?
C4 N1 N2 C12 3.77(16) . . . . ?
C4 C3 C2 C1 177.62(13) . . . . ?
C4 C5 C6 C7 178.16(10) . . . . ?
C4 C5 C10 C9 -179.18(11) . . . . ?
C19 C1 C2 C3 179.46(11) . . . . ?
C19 C24 C23 C22 1.2(2) . . . . ?
C1 C19 C20 C21 -179.78(11) . . . . ?
C1 C19 C24 C23 178.75(12) . . . . ?
C13 C14 C15 C16 -0.97(18) . . . . ?
C13 C18 C17 C16 -0.95(18) . . . . ?
C2 C3 C4 N1 176.34(13) . . . . ?
C2 C3 C4 C5 -3.8(2) . . . . ?
C7 C8 C9 C10 -1.23(19) . . . . ?
C14 C13 C18 C17 2.04(17) . . . . ?
C14 C15 C16 C17 2.07(18) . . . . ?
C18 C13 C14 C15 -1.08(17) . . . . ?
C18 C17 C16 C15 -1.10(19) . . . . ?
C10 C5 C6 C7 -0.04(17) . . . . ?
C10 C5 C4 N1 154.91(11) . . . . ?
C10 C5 C4 C3 -24.97(17) . . . . ?
C9 C8 C7 C6 0.19(18) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C20 C19 C1 N4 176.08(11) . . . . ?
C20 C19 C1 C2 -2.96(19) . . . . ?
C20 C19 C24 C23 -1.26(19) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C24 C19 C1 N4 -3.93(17) . . . . ?
C24 C19 C1 C2 177.03(12) . . . . ?
C24 C19 C20 C21 0.23(19) . . . . ?
C11 O1 C8 C7 7.78(18) . . . . ?
C11 O1 C8 C9 -171.54(11) . . . . ?
C22 C21 C20 C19 0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.186
_oxdiff_exptl_absorpt_empirical_full_min 0.730
####################################################################### 
# 
# 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_k11208-myc-a(oyz0710)_auto
_database_code_depnum_ccdc_archive 'CCDC 2349358'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2024-04-18 deposited with the CCDC.	2025-07-16 downloaded from the CCDC.
;
_audit_creation_date             2023-08-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 Cl2 F N2 O2 S'
_chemical_formula_sum            'C23 H15 Cl2 F N2 O2 S'
_chemical_formula_weight         473.33
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   9.7238(2)
_cell_length_b                   10.1366(2)
_cell_length_c                   11.2215(3)
_cell_angle_alpha                71.447(2)
_cell_angle_beta                 86.430(2)
_cell_angle_gamma                80.166(2)
_cell_volume                     1033.14(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    41557
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9760
_cell_measurement_theta_min      1.9090
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            69896
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.114
_diffrn_reflns_theta_min         2.849
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 100.00   0.50    2.08    --   10.60  13.00 155.00  358
  2  ω   -100.00  78.00   0.50    2.08    --  -10.90  13.00 155.00  356
  3  ω    -15.00 100.00   0.50    2.08    --   10.60  77.00-120.00  230
  4  ω    -17.00 100.00   0.50    2.08    --   10.60  82.00 120.00  234
  5  ω    -79.00  38.00   0.50    2.08    --   10.60 -82.00 120.00  234
  6  ω    -17.00 100.00   0.50    2.08    --   10.60  82.00-180.00  234
  7  ω    -17.00 100.00   0.50    2.08    --   10.60  82.00  60.00  234
  8  ω    -79.00 100.00   0.50    2.08    --   10.60 -13.00 -16.00  358
  9  ω    -79.00  38.00   0.50    2.08    --   10.60 -82.00 -60.00  234
 10  ω    -79.00  36.00   0.50    2.08    --   10.60 -77.00  30.00  230
 11  ω   -100.00  17.00   0.50    2.08    --  -10.90 -82.00-180.00  234
 12  ω   -100.00  17.00   0.50    2.08    --  -10.90 -82.00-120.00  234
 13  ω    -36.00  79.00   0.50    2.08    --  -10.90  77.00 -90.00  230
 14  ω   -100.00  15.00   0.50    2.08    --  -10.90 -77.00 -30.00  230
 15  ω   -100.00  15.00   0.50    2.08    --  -10.90 -77.00-180.00  230
 16  ω   -100.00  78.00   0.50    2.08    --  -10.90 -13.00 -16.00  356
 17  ω    -79.00  33.00   0.50    2.08    --   10.60 -82.00 -90.00  224
 18  ω    -79.00  36.00   0.50    2.08    --   10.60 -62.00  78.03  230
 19  ω    -79.00  38.00   0.50    2.08    --   10.60 -82.00 -12.01  234
 20  ω    -79.00  36.00   0.50    2.08    --   10.60 -62.00 179.48  230
 21  ω    -79.00  38.00   0.50    2.08    --   10.60 -82.00-180.00  234
 22  ω    -79.00  38.00   0.50    2.08    --   10.60 -82.00 150.00  234
 23  ω    -79.00  38.00   0.50    2.08    --   10.60 -82.00-150.00  234
 24  ω    -79.00  36.00   0.50    2.08    --   10.60 -77.00   0.00  230
 25  ω    -79.00  38.00   0.50    2.08    --   10.60 -82.00-120.00  234
 26  ω    -15.00 100.00   0.50    2.08    --   10.60  77.00 -30.00  230
 27  ω    -79.00  36.00   0.50    2.08    --   10.60 -77.00  90.00  230
 28  ω    -20.00 100.00   0.50    2.08    --   10.60  57.00 -30.00  240
 29  ω    -38.00  78.00   0.50    2.08    --  -10.90  82.00 -46.14  232
 30  ω    -41.00  79.00   0.50    2.08    --  -10.90  57.00 -90.00  240
 31  ω    -38.00  79.00   0.50    2.08    --  -10.90  82.00  60.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0737424000
_diffrn_orient_matrix_UB_12      0.0056384000
_diffrn_orient_matrix_UB_13      0.0040699000
_diffrn_orient_matrix_UB_21      -0.0046230000
_diffrn_orient_matrix_UB_22      0.0659675000
_diffrn_orient_matrix_UB_23      0.0106148000
_diffrn_orient_matrix_UB_31      -0.0046777000
_diffrn_orient_matrix_UB_32      0.0347380000
_diffrn_orient_matrix_UB_33      -0.0657001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3925
_reflns_number_total             4400
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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         0.406
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.060
_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)+(0.0354P)²+0.5699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0803
_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:
 C8(H12), C2(H3), C5(H6), C22(H30), C21(H29), C18(H26), C12(H18), C16(H14),
 C19(H27), C13(H17), C15(H15), C14(H16)
2.b Idealised Me refined as rotating group:
 C23(H31A,H31B,H31C)
;
_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 0.68802(4) 0.84363(4) 0.60228(4) 0.01878(10) Uani 1 1 d . . . . .
Cl22 Cl 0.68960(4) 0.68511(4) 0.07688(4) 0.02764(11) Uani 1 1 d . . . . .
Cl23 Cl 0.21582(4) 0.99584(4) -0.14537(4) 0.03037(11) Uani 1 1 d . . . . .
F1 F 0.14410(10) 1.01804(10) 0.10556(9) 0.0317(2) Uani 1 1 d . . . . .
O21 O 0.61064(11) 0.81125(12) 0.71839(11) 0.0263(3) Uani 1 1 d . . . . .
O20 O 0.66590(11) 0.98625(11) 0.51899(11) 0.0253(2) Uani 1 1 d . . . . .
N8 N 0.59531(14) 0.59002(13) 0.35692(12) 0.0238(3) Uani 1 1 d . . . . .
N9 N 0.66125(14) 0.52119(13) 0.46540(12) 0.0234(3) Uani 1 1 d . . . . .
C1 C 0.47728(15) 0.79673(15) 0.20519(14) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.58171(15) 0.80855(15) 0.39956(14) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.554738 0.908012 0.373996 0.022 Uiso 1 1 calc R U . . .
C2 C 0.52571(15) 0.78060(15) 0.08979(14) 0.0188(3) Uani 1 1 d . . . . .
C13 C 0.76151(16) 0.49871(15) 0.65998(14) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.64845(14) 0.73757(15) 0.51156(14) 0.0175(3) Uani 1 1 d . . . . .
C25 C 0.86686(15) 0.79344(15) 0.63417(15) 0.0190(3) Uani 1 1 d . . . . .
C7 C 0.55488(15) 0.72932(15) 0.32455(14) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.27036(15) 0.94126(16) 0.09994(15) 0.0218(3) Uani 1 1 d . . . . .
C10 C 0.68610(15) 0.59024(15) 0.54447(14) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.44824(15) 0.84315(15) -0.01907(14) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.483531 0.831547 -0.096595 0.024 Uiso 1 1 calc R U . . .
C6 C 0.34801(16) 0.88021(16) 0.20760(15) 0.0212(3) Uani 1 1 d . . . . .
H6 H 0.313338 0.895013 0.284140 0.025 Uiso 1 1 calc R U . . .
C30 C 0.96180(16) 0.82569(16) 0.53498(16) 0.0237(3) Uani 1 1 d . . . . .
H30 H 0.930084 0.868890 0.451000 0.028 Uiso 1 1 calc R U . . .
C29 C 1.10230(16) 0.79387(16) 0.56079(16) 0.0247(3) Uani 1 1 d . . . . .
H29 H 1.167607 0.814307 0.493465 0.030 Uiso 1 1 calc R U . . .
C26 C 0.91135(17) 0.72937(18) 0.75695(15) 0.0255(3) Uani 1 1 d . . . . .
H26 H 0.845711 0.706757 0.823728 0.031 Uiso 1 1 calc R U . . .
C18 C 0.70661(17) 0.48733(17) 0.77995(15) 0.0246(3) Uani 1 1 d . . . . .
H18 H 0.617702 0.538774 0.789842 0.030 Uiso 1 1 calc R U . . .
C28 C 1.15102(16) 0.73218(15) 0.68382(16) 0.0230(3) Uani 1 1 d . . . . .
C14 C 0.89073(17) 0.41981(16) 0.64698(16) 0.0267(3) Uani 1 1 d . . . . .
H14 H 0.927051 0.424014 0.565508 0.032 Uiso 1 1 calc R U . . .
C4 C 0.31856(16) 0.92289(15) -0.01337(15) 0.0211(3) Uani 1 1 d . . . . .
C27 C 1.05348(17) 0.69878(18) 0.78076(16) 0.0277(4) Uani 1 1 d . . . . .
H27 H 1.084944 0.654231 0.864686 0.033 Uiso 1 1 calc R U . . .
C31 C 1.30488(16) 0.70616(17) 0.71073(18) 0.0283(4) Uani 1 1 d . . . . .
H31A H 1.354926 0.648195 0.661639 0.042 Uiso 1 1 calc R U . . .
H31B H 1.320447 0.656892 0.800516 0.042 Uiso 1 1 calc R U . . .
H31C H 1.339355 0.796465 0.687542 0.042 Uiso 1 1 calc R U . . .
C17 C 0.78190(18) 0.40090(17) 0.88470(16) 0.0285(4) Uani 1 1 d . . . . .
H17 H 0.744095 0.392920 0.966359 0.034 Uiso 1 1 calc R U . . .
C15 C 0.96623(19) 0.33546(18) 0.75226(18) 0.0334(4) Uani 1 1 d . . . . .
H15 H 1.055324 0.284082 0.742826 0.040 Uiso 1 1 calc R U . . .
C16 C 0.91215(19) 0.32585(18) 0.87126(17) 0.0333(4) Uani 1 1 d . . . . .
H16 H 0.964035 0.268063 0.943493 0.040 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 O21 1.4359(11) . ?
S1 O20 1.4384(12) . ?
S1 C11 1.7963(14) . ?
S1 C25 1.7522(15) . ?
Cl22 C2 1.7410(15) . ?
Cl23 C4 1.7245(16) . ?
F1 C5 1.3462(17) . ?
N8 N9 1.3355(18) . ?
N8 C7 1.3349(19) . ?
N9 C10 1.3473(19) . ?
C1 C2 1.399(2) . ?
C1 C7 1.482(2) . ?
C1 C6 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.373(2) . ?
C12 C7 1.397(2) . ?
C2 C3 1.386(2) . ?
C13 C10 1.483(2) . ?
C13 C18 1.394(2) . ?
C13 C14 1.396(2) . ?
C11 C10 1.407(2) . ?
C25 C30 1.393(2) . ?
C25 C26 1.384(2) . ?
C5 C6 1.375(2) . ?
C5 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C6 H6 0.9500 . ?
C30 H30 0.9500 . ?
C30 C29 1.376(2) . ?
C29 H29 0.9500 . ?
C29 C28 1.397(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.387(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.385(2) . ?
C28 C27 1.394(2) . ?
C28 C31 1.507(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C27 H27 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(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
O21 S1 O20 118.36(7) . . ?
O21 S1 C11 109.17(7) . . ?
O21 S1 C25 109.29(7) . . ?
O20 S1 C11 105.45(7) . . ?
O20 S1 C25 108.17(7) . . ?
C25 S1 C11 105.64(7) . . ?
C7 N8 N9 120.12(13) . . ?
N8 N9 C10 120.84(12) . . ?
C2 C1 C7 123.77(13) . . ?
C6 C1 C2 117.81(14) . . ?
C6 C1 C7 118.42(13) . . ?
C11 C12 H12 121.2 . . ?
C11 C12 C7 117.63(13) . . ?
C7 C12 H12 121.2 . . ?
C1 C2 Cl22 120.80(12) . . ?
C3 C2 Cl22 117.33(11) . . ?
C3 C2 C1 121.83(13) . . ?
C18 C13 C10 122.28(14) . . ?
C18 C13 C14 119.35(15) . . ?
C14 C13 C10 118.35(14) . . ?
C12 C11 S1 116.37(11) . . ?
C12 C11 C10 118.69(13) . . ?
C10 C11 S1 124.87(12) . . ?
C30 C25 S1 118.77(12) . . ?
C26 C25 S1 119.85(12) . . ?
C26 C25 C30 121.30(14) . . ?
N8 C7 C1 116.71(13) . . ?
N8 C7 C12 122.20(14) . . ?
C12 C7 C1 121.08(13) . . ?
F1 C5 C6 119.26(14) . . ?
F1 C5 C4 119.53(14) . . ?
C6 C5 C4 121.19(14) . . ?
N9 C10 C13 114.04(13) . . ?
N9 C10 C11 120.45(14) . . ?
C11 C10 C13 125.41(13) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.13(14) . . ?
C4 C3 H3 120.4 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.44(14) . . ?
C5 C6 H6 119.8 . . ?
C25 C30 H30 120.6 . . ?
C29 C30 C25 118.85(15) . . ?
C29 C30 H30 120.6 . . ?
C30 C29 H29 119.3 . . ?
C30 C29 C28 121.46(15) . . ?
C28 C29 H29 119.3 . . ?
C25 C26 H26 120.6 . . ?
C25 C26 C27 118.82(15) . . ?
C27 C26 H26 120.6 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.88(15) . . ?
C17 C18 H18 120.1 . . ?
C29 C28 C31 120.59(15) . . ?
C27 C28 C29 118.29(14) . . ?
C27 C28 C31 121.10(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.31(16) . . ?
C15 C14 H14 119.8 . . ?
C5 C4 Cl23 119.97(12) . . ?
C5 C4 C3 119.56(14) . . ?
C3 C4 Cl23 120.46(12) . . ?
C26 C27 C28 121.24(16) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.50(16) . . ?
C16 C17 H17 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.12(16) . . ?
C16 C15 H15 119.9 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.79(16) . . ?
C15 C16 H16 120.1 . . ?

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 C11 C10 N9 -174.79(11) . . . . ?
S1 C11 C10 C13 1.3(2) . . . . ?
S1 C25 C30 C29 176.19(12) . . . . ?
S1 C25 C26 C27 -175.91(12) . . . . ?
Cl22 C2 C3 C4 -178.50(11) . . . . ?
F1 C5 C6 C1 178.09(13) . . . . ?
F1 C5 C4 Cl23 -1.0(2) . . . . ?
F1 C5 C4 C3 -179.63(13) . . . . ?
O21 S1 C11 C12 115.49(12) . . . . ?
O21 S1 C11 C10 -67.41(14) . . . . ?
O21 S1 C25 C30 -175.00(11) . . . . ?
O21 S1 C25 C26 1.81(14) . . . . ?
O20 S1 C11 C12 -12.66(13) . . . . ?
O20 S1 C11 C10 164.44(12) . . . . ?
O20 S1 C25 C30 -44.87(13) . . . . ?
O20 S1 C25 C26 131.94(12) . . . . ?
N8 N9 C10 C13 -179.40(13) . . . . ?
N8 N9 C10 C11 -2.8(2) . . . . ?
N9 N8 C7 C1 -177.57(13) . . . . ?
N9 N8 C7 C12 1.4(2) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C12 C11 C10 N9 2.2(2) . . . . ?
C12 C11 C10 C13 178.38(14) . . . . ?
C2 C1 C7 N8 -53.3(2) . . . . ?
C2 C1 C7 C12 127.73(15) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C2 C3 C4 Cl23 -177.11(11) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C13 C18 C17 C16 0.3(2) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C11 S1 C25 C30 67.65(13) . . . . ?
C11 S1 C25 C26 -115.54(13) . . . . ?
C11 C12 C7 N8 -1.9(2) . . . . ?
C11 C12 C7 C1 177.03(13) . . . . ?
C25 S1 C11 C12 -127.08(11) . . . . ?
C25 S1 C11 C10 50.02(14) . . . . ?
C25 C30 C29 C28 -0.9(2) . . . . ?
C25 C26 C27 C28 0.4(2) . . . . ?
C7 N8 N9 C10 1.0(2) . . . . ?
C7 C1 C2 Cl22 -3.6(2) . . . . ?
C7 C1 C2 C3 178.56(13) . . . . ?
C7 C1 C6 C5 -177.97(13) . . . . ?
C7 C12 C11 S1 177.37(10) . . . . ?
C7 C12 C11 C10 0.1(2) . . . . ?
C10 C13 C18 C17 -179.61(14) . . . . ?
C10 C13 C14 C15 178.50(14) . . . . ?
C6 C1 C2 Cl22 176.93(11) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C7 N8 126.18(15) . . . . ?
C6 C1 C7 C12 -52.83(19) . . . . ?
C6 C5 C4 Cl23 177.72(12) . . . . ?
C6 C5 C4 C3 -0.9(2) . . . . ?
C30 C25 C26 C27 0.8(2) . . . . ?
C30 C29 C28 C27 2.1(2) . . . . ?
C30 C29 C28 C31 -176.33(14) . . . . ?
C29 C28 C27 C26 -1.9(2) . . . . ?
C26 C25 C30 C29 -0.6(2) . . . . ?
C18 C13 C10 N9 -121.86(15) . . . . ?
C18 C13 C10 C11 61.8(2) . . . . ?
C18 C13 C14 C15 -2.6(2) . . . . ?
C18 C17 C16 C15 -1.1(2) . . . . ?
C14 C13 C10 N9 57.00(18) . . . . ?
C14 C13 C10 C11 -119.36(16) . . . . ?
C14 C13 C18 C17 1.5(2) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C31 C28 C27 C26 176.58(15) . . . . ?

_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 1.664
_oxdiff_exptl_absorpt_empirical_full_min 0.544
