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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_az14335492_100k_mo1
_database_code_depnum_ccdc_archive 'CCDC 2517062'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 F N2 O4 S'
_chemical_formula_sum            'C16 H21 F N2 O4 S'
_chemical_formula_weight         356.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S F'
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'
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                   8.6550(3)
_cell_length_b                   9.8060(3)
_cell_length_c                   10.8320(3)
_cell_angle_alpha                79.328(2)
_cell_angle_beta                 86.612(2)
_cell_angle_gamma                78.397(2)
_cell_volume                     884.73(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7636
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.2980
_cell_measurement_theta_min      2.8860
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -1 0.0623
-1 0 -5 0.0325
1 1 5 0.0195
-1 5 0 0.0506
2 1 -2 0.0149
-2 -1 2 0.0234
-5 -2 -4 0.0278

_exptl_crystal_preparation       
'The material was recrystallized from DMSO by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow evaporation'
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.038
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9995 -4.9986 -0.9995 0.0358 0.0843 -0.3837
-0.9996 0.0001 -4.9987 0.0174 0.3245 0.1055
0.9997 0.9996 4.9986 -0.0055 -0.3317 -0.0318
-0.9995 4.9986 -0.0003 -0.0170 -0.0222 0.3988
1.9996 0.9998 -1.9997 0.2031 0.0893 0.0432
-1.9996 -0.9998 1.9997 -0.2031 -0.0893 -0.0432
-4.9988 -1.9994 -3.9986 -0.3323 0.3323 0.0643

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19570
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.621
_diffrn_reflns_theta_min         2.403
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  37.00   0.50   62.05    --    4.08-108.00-155.00   74
  2  ω      0.00  45.00   0.50   62.05    --   -4.71-108.00-155.00   90
  3  ω    -20.00  82.00   0.50   62.05    --    0.00  33.00  65.04  204
  4  ω    -46.00  33.00   0.50   62.05    --    4.08 -77.00-150.00  158
  5  ω    -45.00  34.00   0.50   62.05    --    4.08 -77.00 -60.00  158
  6  ω     -8.00  33.00   0.50   62.05    --    4.08  57.00-150.00   82
  7  ω     51.00  80.00   0.50   62.05    --    4.08  57.00-150.00   58
  8  ω      3.00  30.00   0.50   62.05    --    4.08 -99.00  90.00   54
  9  ω    -15.00  12.00   0.50   62.05    --    4.08 -99.00 -90.00   54
 10  ω    -31.00  44.00   0.50   62.05    --   -4.71  77.00  90.00  150
 11  ω    -35.00  46.00   0.50   62.05    --   -4.71  77.00   0.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0767570000
_diffrn_orient_matrix_UB_12      0.0119456000
_diffrn_orient_matrix_UB_13      -0.0188327000
_diffrn_orient_matrix_UB_21      -0.0138848000
_diffrn_orient_matrix_UB_22      -0.0072132000
_diffrn_orient_matrix_UB_23      -0.0621390000
_diffrn_orient_matrix_UB_31      -0.0303076000
_diffrn_orient_matrix_UB_32      0.0737209000
_diffrn_orient_matrix_UB_33      -0.0150503000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3552
_reflns_number_total             4474
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.416
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.023
_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)+(0.0452P)²+0.3840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          
'F1 and O4 are refined as disorder with occupancy approximately 0.53: 0.47'
_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. Restrained distances
 S1-O4A = S1-O4B
 1.424 with sigma of 0.001
 S1-O4A \\sim S1-O4B
 with sigma of 0.02
 S1-F1A \\sim S1-F1B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1B) = Uanis(O4A)
4. Others
 Sof(F1B)=Sof(O4B)=1-FVAR(1)
 Sof(F1A)=Sof(O4A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4)
5.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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 0.62258(4) 0.63789(4) 0.60194(4) 0.02654(11) Uani 1 1 d D . . . .
F1A F 0.6684(17) 0.4841(8) 0.5813(14) 0.043(3) Uani 0.538(17) 1 d D . P A 1
F1B F 0.697(4) 0.638(5) 0.7273(17) 0.039(2) Uani 0.462(17) 1 d D . P A 2
O1 O 0.97376(12) 0.96583(11) 0.21857(10) 0.0247(2) Uani 1 1 d . . . . .
O2 O 0.19563(13) 0.73903(13) 0.65030(11) 0.0342(3) Uani 1 1 d . . . . .
O3 O 0.37249(12) 0.55001(11) 0.74292(10) 0.0251(2) Uani 1 1 d . . . . .
O4A O 0.696(4) 0.626(5) 0.7189(18) 0.039(2) Uani 0.538(17) 1 d D . P A 1
O4B O 0.652(2) 0.5030(9) 0.5647(17) 0.0330(18) Uani 0.462(17) 1 d D . P A 2
N1 N 0.58528(17) 1.10443(16) 0.13687(15) 0.0388(4) Uani 1 1 d . . . . .
N2 N 0.45310(15) 0.71190(14) 0.58769(12) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.64952(17) 0.84070(15) 0.39760(14) 0.0217(3) Uani 1 1 d . . . . .
H1 H 0.537573 0.860818 0.395259 0.026 Uiso 1 1 calc R U . . .
C2 C 0.72719(17) 0.73649(15) 0.48958(13) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.89165(17) 0.70683(17) 0.49333(14) 0.0249(3) Uani 1 1 d . . . . .
H3 H 0.943349 0.634789 0.556900 0.030 Uiso 1 1 calc R U . . .
C4 C 0.97954(17) 0.78136(17) 0.40543(14) 0.0241(3) Uani 1 1 d . . . . .
H4 H 1.091403 0.760735 0.408974 0.029 Uiso 1 1 calc R U . . .
C5 C 0.90480(16) 0.88722(15) 0.31101(13) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.73814(17) 0.91528(15) 0.30883(13) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.65648(17) 1.02235(17) 0.21201(15) 0.0265(3) Uani 1 1 d . . . . .
C8 C 1.14455(17) 0.97002(16) 0.21111(15) 0.0243(3) Uani 1 1 d . . . . .
C9 C 1.1926(2) 1.0118(2) 0.32908(18) 0.0370(4) Uani 1 1 d . . . . .
H9A H 1.112190 1.089541 0.351710 0.056 Uiso 1 1 calc R U . . .
H9B H 1.294070 1.042512 0.313796 0.056 Uiso 1 1 calc R U . . .
H9C H 1.202463 0.930479 0.397988 0.056 Uiso 1 1 calc R U . . .
C10 C 1.2402(2) 0.83210(18) 0.18253(17) 0.0367(4) Uani 1 1 d . . . . .
H10A H 1.238850 0.757537 0.256388 0.055 Uiso 1 1 calc R U . . .
H10B H 1.349254 0.842872 0.161256 0.055 Uiso 1 1 calc R U . . .
H10C H 1.194541 0.806457 0.111424 0.055 Uiso 1 1 calc R U . . .
C11 C 1.15220(19) 1.08761(19) 0.09935(19) 0.0383(4) Uani 1 1 d . . . . .
H11A H 1.107629 1.065411 0.026067 0.057 Uiso 1 1 calc R U . . .
H11B H 1.262359 1.096330 0.080831 0.057 Uiso 1 1 calc R U . . .
H11C H 1.091550 1.177027 0.119007 0.057 Uiso 1 1 calc R U . . .
C12 C 0.32676(17) 0.67032(16) 0.66206(14) 0.0243(3) Uani 1 1 d . . . . .
C13 C 0.26328(16) 0.49842(16) 0.84352(13) 0.0220(3) Uani 1 1 d . . . . .
C14 C 0.1169(2) 0.4725(2) 0.78845(17) 0.0365(4) Uani 1 1 d . . . . .
H14A H 0.044977 0.563018 0.762430 0.055 Uiso 1 1 calc R U . . .
H14B H 0.064063 0.411515 0.851932 0.055 Uiso 1 1 calc R U . . .
H14C H 0.147102 0.426294 0.715418 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2260(2) 0.6031(2) 0.93177(16) 0.0369(4) Uani 1 1 d . . . . .
H15A H 0.324447 0.618326 0.962266 0.055 Uiso 1 1 calc R U . . .
H15B H 0.162265 0.566065 1.003178 0.055 Uiso 1 1 calc R U . . .
H15C H 0.167001 0.692970 0.887329 0.055 Uiso 1 1 calc R U . . .
C16 C 0.3623(2) 0.36014(19) 0.90575(19) 0.0391(4) Uani 1 1 d . . . . .
H16A H 0.378990 0.292534 0.847726 0.059 Uiso 1 1 calc R U . . .
H16B H 0.307625 0.321803 0.982145 0.059 Uiso 1 1 calc R U . . .
H16C H 0.464505 0.376533 0.927660 0.059 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 F1A 1.535(5) . ?
S1 F1B 1.535(6) . ?
S1 O4A 1.4241(10) . ?
S1 O4B 1.4241(10) . ?
S1 N2 1.5031(13) . ?
S1 C2 1.7384(14) . ?
O1 C5 1.3347(17) . ?
O1 C8 1.4841(17) . ?
O2 C12 1.1983(18) . ?
O3 C12 1.3365(18) . ?
O3 C13 1.4843(16) . ?
N1 C7 1.143(2) . ?
N2 C12 1.4016(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(2) . ?
C1 C6 1.3877(19) . ?
C2 C3 1.396(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(2) . ?
C5 C6 1.4139(19) . ?
C6 C7 1.443(2) . ?
C8 C9 1.516(2) . ?
C8 C10 1.512(2) . ?
C8 C11 1.518(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.517(2) . ?
C13 C15 1.505(2) . ?
C13 C16 1.513(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
F1A S1 C2 106.7(5) . . ?
F1B S1 C2 104.7(16) . . ?
O4A S1 F1A 100(2) . . ?
O4A S1 N2 118.6(16) . . ?
O4A S1 C2 106.5(18) . . ?
O4B S1 F1B 114(2) . . ?
O4B S1 N2 112.7(8) . . ?
O4B S1 C2 103.2(8) . . ?
N2 S1 F1A 118.8(6) . . ?
N2 S1 F1B 115.7(15) . . ?
N2 S1 C2 105.21(7) . . ?
C5 O1 C8 124.41(11) . . ?
C12 O3 C13 120.86(11) . . ?
C12 N2 S1 124.87(11) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.79(13) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 S1 120.86(11) . . ?
C1 C2 C3 120.73(13) . . ?
C3 C2 S1 118.41(11) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.44(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.31(13) . . ?
C5 C4 H4 119.8 . . ?
O1 C5 C4 127.10(13) . . ?
O1 C5 C6 114.60(12) . . ?
C4 C5 C6 118.29(13) . . ?
C1 C6 C5 121.44(13) . . ?
C1 C6 C7 118.50(13) . . ?
C5 C6 C7 120.05(13) . . ?
N1 C7 C6 176.64(16) . . ?
O1 C8 C9 109.92(12) . . ?
O1 C8 C10 110.48(13) . . ?
O1 C8 C11 101.62(12) . . ?
C9 C8 C11 110.04(15) . . ?
C10 C8 C9 114.20(14) . . ?
C10 C8 C11 109.86(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 126.71(14) . . ?
O2 C12 N2 121.32(14) . . ?
O3 C12 N2 111.98(12) . . ?
O3 C13 C14 111.07(12) . . ?
O3 C13 C15 108.50(12) . . ?
O3 C13 C16 101.86(11) . . ?
C15 C13 C14 112.83(14) . . ?
C15 C13 C16 111.52(14) . . ?
C16 C13 C14 110.52(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 N2 C12 O2 175.61(13) . . . . ?
S1 N2 C12 O3 -4.3(2) . . . . ?
S1 C2 C3 C4 179.37(12) . . . . ?
F1A S1 N2 C12 62.4(6) . . . . ?
F1A S1 C2 C1 116.0(6) . . . . ?
F1A S1 C2 C3 -63.2(6) . . . . ?
F1B S1 N2 C12 -63.4(19) . . . . ?
F1B S1 C2 C1 -133.4(17) . . . . ?
F1B S1 C2 C3 47.4(17) . . . . ?
O1 C5 C6 C1 179.00(13) . . . . ?
O1 C5 C6 C7 -0.3(2) . . . . ?
O4A S1 N2 C12 -59(2) . . . . ?
O4A S1 C2 C1 -138(2) . . . . ?
O4A S1 C2 C3 43(2) . . . . ?
O4B S1 N2 C12 69.9(8) . . . . ?
O4B S1 C2 C1 107.3(8) . . . . ?
O4B S1 C2 C3 -71.9(8) . . . . ?
N2 S1 C2 C1 -11.00(15) . . . . ?
N2 S1 C2 C3 169.81(13) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 S1 N2 C12 -178.40(13) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C1 C6 C7 179.07(15) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 O1 -178.58(14) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 -179.18(15) . . . . ?
C5 O1 C8 C9 -56.58(18) . . . . ?
C5 O1 C8 C10 70.34(18) . . . . ?
C5 O1 C8 C11 -173.11(14) . . . . ?
C6 C1 C2 S1 -179.09(12) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C8 O1 C5 C4 -10.1(2) . . . . ?
C8 O1 C5 C6 171.11(13) . . . . ?
C12 O3 C13 C14 60.15(18) . . . . ?
C12 O3 C13 C15 -64.42(17) . . . . ?
C12 O3 C13 C16 177.84(14) . . . . ?
C13 O3 C12 O2 -9.3(2) . . . . ?
C13 O3 C12 N2 170.61(12) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_50
_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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.850
####################################################################### 
# 
# 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_az15042516_100k_fi
_database_code_depnum_ccdc_archive 'CCDC 2517074'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2025-12-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 Cl F N O4 S'
_chemical_formula_sum            'C10 H9 Cl F N O4 S'
_chemical_formula_weight         293.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S F N C O Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.0402(5)
_cell_length_b                   8.2666(2)
_cell_length_c                   10.7074(2)
_cell_angle_alpha                104.1960(10)
_cell_angle_beta                 90.634(4)
_cell_angle_gamma                92.555(4)
_cell_volume                     603.37(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8336
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.2600
_cell_measurement_theta_min      4.2500
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    4.641
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.95a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -4 -3 0.0240
0 4 3 0.0130
3 3 2 0.0286
4 0 -1 0.0354
-5 -1 1 0.0344
0 2 5 0.0072
4 -1 4 0.0275
0 1 -5 0.0152
0 -1 5 0.0082

_exptl_crystal_preparation       
'The material was recrystallised from a mixture of DCM and heptane by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and heptane by slow evaporation'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0007 -3.9986 -2.9971 -0.0619 -0.7549 0.6204
0.0007 3.9986 2.9971 0.0619 0.7549 -0.6204
3.0001 2.9994 1.9977 0.0120 0.9909 0.0353
3.9990 0.0006 -0.9996 0.0249 0.5184 0.7173
-4.9986 -1.0004 0.9999 -0.0996 -0.8007 -0.7788
0.0023 1.9992 4.9959 -0.3403 0.6292 -0.5717
4.0020 -0.9992 3.9967 -0.6005 0.7431 0.4428
-0.0030 0.9998 -4.9963 0.6254 -0.2248 0.2745
0.0030 -0.9998 4.9963 -0.6254 0.2248 -0.2745

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.000
_diffrn_reflns_theta_min         4.260
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  79.00   0.50    5.61    --   52.50 -82.00  85.00  184
  2  ω    -13.00  79.00   0.50    5.61    --   52.50 -82.00  85.00  184
  3  ω   -143.00 -79.00   0.50   11.71    --  -77.61 -82.00  85.00  128
  4  ω   -103.00 -12.00   0.50   11.71    --  -77.61  82.00-153.00  182
  5  ω    101.00 161.00   0.50   11.71    --   95.27  82.00-153.00  120
  6  ω     29.00 121.00   0.50   11.71    --   95.27 -82.00  85.00  184
  7  ω     80.00 119.00   0.50    5.61    --   52.50  77.00-180.00   78
  8  ω     34.00 104.00   0.50    5.61    --   52.50-125.00  30.00  140
  9  ω   -119.00 -80.00   0.50    5.61    --  -53.06 -77.00  60.00   78
 10  ω    -79.00  13.00   0.50    5.61    --  -53.06  82.00-153.00  184
 11  ω   -119.00 -80.00   0.50    5.61    --  -53.06 -77.00 150.00   78
 12  ω   -147.00 -76.00   0.50   11.71    --  -77.61-125.00 150.00  142
 13  ω   -144.00 -80.00   0.50   11.71    --  -77.61 -77.00 150.00  128
 14  ω   -158.00 -69.00   0.50   11.71    --  -86.25 -64.00  40.84  178
 15  ω   -156.00 -68.00   0.50   11.71    --  -86.25 -68.00   9.94  176
 16  ω     29.00 106.00   0.50   11.71    --   95.27 -99.00 -60.00  154
 17  ω     29.00 106.00   0.50   11.71    --   95.27 -99.00-150.00  154
 18  ω     29.00 106.00   0.50   11.71    --   95.27 -99.00  30.00  154
 19  ω     82.00 172.00   0.50   11.71    --   95.27  38.00 120.00  180
 20  ω     19.00 108.00   0.50   11.71    --   95.27 -38.00  90.00  178
 21  ω     29.00 106.00   0.50   11.71    --   95.27 -99.00 -90.00  154
 22  ω     29.00 106.00   0.50   11.71    --   95.27 -99.00  90.00  154
 23  ω     19.00 108.00   0.50   11.71    --   95.27 -38.00-120.00  178
 24  ω     -6.00  21.00   0.50    5.61    --   30.00  99.00  97.35   54
 25  ω      4.00  31.00   0.50    5.61    --   34.00  88.00 -95.85   54
 26  ω      6.00  33.00   0.50    5.61    --   34.00  86.00-149.31   54
 27  ω      4.00  30.00   0.50    5.61    --   34.00  89.00  32.24   52
 28  ω     38.00 127.00   0.50    5.61    --   58.00  72.00 -89.26  178
 29  ω   -140.00 -52.00   0.50    5.61    --  -70.00 -67.00  95.99  176
 30  ω   -140.00 -52.00   0.50    5.61    --  -70.00 -67.00 -21.45  176
 31  ω   -139.00 -50.00   0.50    5.61    --  -70.00 -72.00   2.32  178
 32  ω   -144.00 -56.00   0.50    5.61    --  -74.00 -68.00  56.01  176
 33  ω   -148.00 -60.00   0.50   11.71    --  -78.00 -67.00 121.51  176
 34  ω   -147.00 -59.00   0.50   11.71    --  -78.00 -70.00-170.92  176
 35  ω   -150.00 -61.00   0.50   11.71    --  -78.00 -62.00-113.02  178
 36  ω   -155.00 -65.00   0.50   11.71    --  -82.00 -60.00-161.39  180
 37  ω   -155.00 -65.00   0.50   11.71    --  -82.00 -59.00 142.19  180
 38  ω   -153.00 -64.00   0.50   11.71    --  -82.00 -64.00 -72.67  178
 39  ω   -157.00 -68.00   0.50   11.71    --  -86.25 -66.00-129.60  178
 40  ω   -156.00 -67.00   0.50   11.71    --  -86.25 -70.00 -44.97  178
 41  ω   -156.00 -68.00   0.50   11.71    --  -86.25 -69.00  81.66  176
 42  ω   -157.00-124.00   0.50   11.71    --  -86.25 -66.00 100.92   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0203181000
_diffrn_orient_matrix_UB_12      0.0950281000
_diffrn_orient_matrix_UB_13      -0.1061355000
_diffrn_orient_matrix_UB_21      0.1475736000
_diffrn_orient_matrix_UB_22      0.1348868000
_diffrn_orient_matrix_UB_23      0.0718929000
_diffrn_orient_matrix_UB_31      0.1606651000
_diffrn_orient_matrix_UB_32      -0.0990756000
_diffrn_orient_matrix_UB_33      -0.0748575000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1986
_reflns_number_total             2352
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.44.95a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.95a 64-bit (release 24-02-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.95a (Rigaku OD, 2025)'
_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         0.433
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.117
_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)+(0.0600P)²+0.2881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1229
_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:
 C2(H2), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_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 0.21811(9) 0.61867(9) 0.60004(6) 0.0426(2) Uani 1 1 d . . . . .
S1 S 0.62874(8) 0.80879(8) 0.22570(6) 0.0335(2) Uani 1 1 d . . . . .
F1 F 0.6995(2) 0.6313(2) 0.16379(14) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.7856(3) 0.9225(3) 0.22044(18) 0.0415(5) Uani 1 1 d . . . . .
O2 O 0.5213(3) 0.7990(3) -0.03943(17) 0.0411(5) Uani 1 1 d . . . . .
O16 O 0.2961(2) 0.5165(2) 0.24865(16) 0.0323(4) Uani 1 1 d . . . . .
O18 O 0.1087(3) 0.7255(3) 0.33971(18) 0.0399(5) Uani 1 1 d . . . . .
N1 N 0.4337(3) 0.8247(3) 0.17162(19) 0.0322(5) Uani 1 1 d . . . . .
C1 C 0.4163(4) 0.7161(3) 0.5498(2) 0.0305(5) Uani 1 1 d . . . . .
C2 C 0.5620(4) 0.7816(3) 0.6384(2) 0.0331(6) Uani 1 1 d . . . . .
H2 H 0.550512 0.775882 0.725605 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7232(4) 0.8548(3) 0.6001(2) 0.0351(6) Uani 1 1 d . . . . .
H3 H 0.822723 0.900366 0.660879 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7405(4) 0.8620(3) 0.4722(2) 0.0332(6) Uani 1 1 d . . . . .
H4 H 0.851706 0.911823 0.444992 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5936(3) 0.7958(3) 0.3853(2) 0.0281(5) Uani 1 1 d . . . . .
C6 C 0.4259(3) 0.7233(3) 0.4218(2) 0.0282(5) Uani 1 1 d . . . . .
C7 C 0.2583(4) 0.6587(3) 0.3322(2) 0.0315(5) Uani 1 1 d . . . . .
C8 C 0.1454(4) 0.4470(4) 0.1554(3) 0.0398(6) Uani 1 1 d . . . . .
H8A H 0.185634 0.343333 0.097843 0.060 Uiso 1 1 calc R U . . .
H8B H 0.117389 0.527345 0.104735 0.060 Uiso 1 1 calc R U . . .
H8C H 0.030985 0.423115 0.200380 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4012(4) 0.8270(3) 0.0422(2) 0.0341(6) Uani 1 1 d . . . . .
C10 C 0.2020(4) 0.8702(4) 0.0174(3) 0.0433(7) Uani 1 1 d . . . . .
H10A H 0.187509 0.989639 0.054408 0.065 Uiso 1 1 calc R U . . .
H10B H 0.112247 0.805070 0.057296 0.065 Uiso 1 1 calc R U . . .
H10C H 0.176132 0.844128 -0.075697 0.065 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 C1 1.736(3) . ?
S1 F1 1.5605(17) . ?
S1 O1 1.429(2) . ?
S1 N1 1.508(2) . ?
S1 C5 1.758(2) . ?
O2 C9 1.211(3) . ?
O16 C7 1.331(3) . ?
O16 C8 1.447(3) . ?
O18 C7 1.204(3) . ?
N1 C9 1.408(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 C6 1.403(3) . ?
C6 C7 1.505(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.499(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
F1 S1 C5 101.06(10) . . ?
O1 S1 F1 105.58(11) . . ?
O1 S1 N1 122.82(12) . . ?
O1 S1 C5 110.30(12) . . ?
N1 S1 F1 109.35(11) . . ?
N1 S1 C5 105.65(11) . . ?
C7 O16 C8 115.1(2) . . ?
C9 N1 S1 122.72(17) . . ?
C2 C1 Cl1 118.82(19) . . ?
C2 C1 C6 122.0(2) . . ?
C6 C1 Cl1 119.1(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 S1 115.97(19) . . ?
C4 C5 C6 122.3(2) . . ?
C6 C5 S1 121.73(18) . . ?
C1 C6 C5 116.6(2) . . ?
C1 C6 C7 119.4(2) . . ?
C5 C6 C7 124.0(2) . . ?
O16 C7 C6 110.88(19) . . ?
O18 C7 O16 125.4(2) . . ?
O18 C7 C6 123.7(2) . . ?
O16 C8 H8A 109.5 . . ?
O16 C8 H8B 109.5 . . ?
O16 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N1 123.7(2) . . ?
O2 C9 C10 124.0(2) . . ?
N1 C9 C10 112.3(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
Cl1 C1 C2 C3 177.98(19) . . . . ?
Cl1 C1 C6 C5 -176.79(17) . . . . ?
Cl1 C1 C6 C7 4.7(3) . . . . ?
S1 N1 C9 O2 8.1(4) . . . . ?
S1 N1 C9 C10 -171.1(2) . . . . ?
S1 C5 C6 C1 178.33(17) . . . . ?
S1 C5 C6 C7 -3.2(3) . . . . ?
F1 S1 N1 C9 -67.6(2) . . . . ?
F1 S1 C5 C4 97.3(2) . . . . ?
F1 S1 C5 C6 -83.1(2) . . . . ?
O1 S1 N1 C9 56.8(3) . . . . ?
O1 S1 C5 C4 -14.1(2) . . . . ?
O1 S1 C5 C6 165.58(18) . . . . ?
N1 S1 C5 C4 -148.80(19) . . . . ?
N1 S1 C5 C6 30.8(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 C6 C7 O16 -108.4(2) . . . . ?
C1 C6 C7 O18 69.1(3) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C1 C6 C7 -176.5(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 S1 -179.43(18) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C4 C5 C6 C7 176.4(2) . . . . ?
C5 S1 N1 C9 -175.6(2) . . . . ?
C5 C6 C7 O16 73.2(3) . . . . ?
C5 C6 C7 O18 -109.3(3) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C8 O16 C7 O18 4.4(3) . . . . ?
C8 O16 C7 C6 -178.1(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_6408
_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 2.172
_oxdiff_exptl_absorpt_empirical_full_min 0.529
####################################################################### 
# 
# 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_az14335492_100k_cu1
_database_code_depnum_ccdc_archive 'CCDC 2517063'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 F N2 O4 S'
_chemical_formula_sum            'C16 H21 F N2 O4 S'
_chemical_formula_weight         356.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.6495(2)
_cell_length_b                   9.8157(2)
_cell_length_c                   10.8278(3)
_cell_angle_alpha                79.359(2)
_cell_angle_beta                 86.586(2)
_cell_angle_gamma                78.339(2)
_cell_volume                     884.60(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6930
_cell_measurement_theta_min      4.1370
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    1.918
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -1 0.0623
-1 0 -5 0.0325
1 1 5 0.0195
-1 5 0 0.0506
2 1 -2 0.0149
-2 -1 2 0.0234
-5 -2 -4 0.0278

_exptl_crystal_preparation       
'The material was recrystallized from DMSO by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow evaporation'
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.038
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0085 -4.9965 -0.9971 0.0805 0.1825 -0.8333
-0.9960 0.0006 -5.0039 0.0381 0.7056 0.2291
0.9946 0.9993 5.0035 -0.0126 -0.7212 -0.0690
-1.0077 4.9971 -0.0034 -0.0395 -0.0474 0.8660
2.0010 1.0056 -1.9986 0.4414 0.1940 0.0944
-2.0010 -1.0056 1.9986 -0.4414 -0.1940 -0.0944
-4.9955 -2.0088 -4.0082 -0.7218 0.7228 0.1383

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.379
_diffrn_reflns_theta_min         4.155
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  43.00   0.50    0.15    --   44.00  79.00  84.31   54
  2  ω     16.00  43.00   0.50    0.15    --   44.00  79.00  20.27   54
  3  ω     16.00  43.00   0.50    0.15    --   44.00  79.00 -26.58   54
  4  ω      9.00  43.00   0.50    0.15    --   36.00  78.00-111.81   68
  5  ω      8.00  43.00   0.50    0.15    --   36.00  79.00-162.57   70
  6  ω    -41.00 -13.00   0.50    0.15    --   16.00 126.00 108.47   56
  7  ω      2.00  29.00   0.50    0.15    --   36.00  90.00 -47.97   54
  8  ω    104.00 170.00   0.50    0.60    --   96.59 109.00 -58.00  132
  9  ω    104.00 178.00   0.50    0.60    --  108.39 109.00 -58.00  148
 10  ω     95.00 171.00   0.50    0.60    --   96.59 125.00-120.00  152
 11  ω     80.00 165.00   0.50    0.60    --   96.59  77.00 -90.00  170
 12  ω     37.00 131.00   0.50    0.15    --   60.00  71.00 -12.85  188
 13  ω     88.00 178.00   0.50    0.60    --  108.39  61.00   0.00  180
 14  ω     92.00 178.00   0.50    0.60    --  108.39  45.00  30.00  172
 15  ω     40.00 135.00   0.50    0.15    --   60.00  59.00 103.43  190
 16  ω     19.00 113.00   0.50    0.60    --   96.59 -45.00 -60.00  188
 17  ω     22.00  97.00   0.50    0.15    --   50.45-109.00-154.00  150
 18  ω     34.00 112.00   0.50    0.60    --   96.59-125.00-180.00  156
 19  ω     35.00 107.00   0.50    0.60    --  108.39-109.00-154.00  144
 20  ω     23.00 107.00   0.50    0.60    --   96.59-109.00-154.00  168
 21  ω     28.00 105.00   0.50    0.60    --   96.59 -95.00-120.00  154
 22  ω     40.00 105.00   0.50    0.60    --  108.39 -95.00 -90.00  130
 23  ω     34.00 129.00   0.50    0.60    --  108.39 -61.00   0.00  190
 24  ω     40.00 105.00   0.50    0.60    --  108.39 -95.00   0.00  130
 25  ω     34.00 112.00   0.50    0.60    --   96.59-125.00 120.00  156
 26  ω    -82.00  -1.00   0.50    0.15    --  -51.20 109.00 -58.00  162
 27  ω    -82.00  -6.00   0.50    0.60    --  -79.95 109.00 -58.00  152
 28  ω   -120.00 -80.00   0.50    0.15    --  -51.20 -77.00-150.00   80
 29  ω   -120.00 -80.00   0.50    0.15    --  -51.20 -77.00 -90.00   80
 30  ω   -160.00 -65.00   0.50    0.60    --  -88.00 -69.00 -84.25  190
 31  ω   -148.00 -80.00   0.50    0.60    --  -79.95 -77.00 -30.00  136
 32  ω   -120.00 -80.00   0.50    0.15    --  -51.20 -77.00 -30.00   80
 33  ω   -163.00 -68.00   0.50    0.60    --  -88.50 -60.00-144.54  190
 34  ω   -156.00-127.00   0.50    0.60    --  -84.00 -68.00  96.17   58
 35  ω   -160.00 -66.00   0.50    0.60    --  -88.50 -69.00 140.89  188
 36  ω   -120.00 -80.00   0.50    0.15    --  -51.20 -77.00  60.00   80
 37  ω   -149.00 -86.00   0.50    0.60    --  -79.95 -95.00  60.00  126
 38  ω   -153.00 -82.00   0.50    0.60    --  -79.95-109.00-154.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1669019000
_diffrn_orient_matrix_UB_12      0.0257224000
_diffrn_orient_matrix_UB_13      -0.0408303000
_diffrn_orient_matrix_UB_21      -0.0300401000
_diffrn_orient_matrix_UB_22      -0.0156455000
_diffrn_orient_matrix_UB_23      -0.1350379000
_diffrn_orient_matrix_UB_31      -0.0658304000
_diffrn_orient_matrix_UB_32      0.1600062000
_diffrn_orient_matrix_UB_33      -0.0326574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3107
_reflns_number_total             3590
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.225
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.093
_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)+(0.0444P)²+0.3825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          
'F1 and O4 are refined as disorder with occupancy approximately 0.52: 0.48'
_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. Restrained distances
 S1-F1A
 0.001 with sigma of 1.562
 S1-O4B
 1.424 with sigma of 0.001
3. Others
 Sof(F1B)=Sof(O4B)=1-FVAR(1)
 Sof(F1A)=Sof(O4A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4)
4.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.62250(5) 0.63810(5) 0.60176(4) 0.03220(13) Uani 1 1 d D . . . .
O1 O 0.97375(13) 0.96599(13) 0.21840(11) 0.0302(3) Uani 1 1 d . . . . .
O2 O 0.19520(14) 0.73919(14) 0.65016(12) 0.0395(3) Uani 1 1 d . . . . .
O3 O 0.37234(13) 0.54997(12) 0.74262(11) 0.0305(3) Uani 1 1 d . . . . .
N1 N 0.58512(18) 1.10456(19) 0.13669(16) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.45336(16) 0.71184(16) 0.58740(13) 0.0312(3) Uani 1 1 d . . . . .
C1 C 0.64927(18) 0.84058(17) 0.39747(15) 0.0273(3) Uani 1 1 d . . . . .
H1 H 0.537224 0.860599 0.395142 0.033 Uiso 1 1 calc R U . . .
C2 C 0.72710(19) 0.73641(18) 0.48952(15) 0.0274(3) Uani 1 1 d . . . . .
C3 C 0.89153(19) 0.70702(19) 0.49316(16) 0.0302(4) Uani 1 1 d . . . . .
H3 H 0.943339 0.635024 0.556677 0.036 Uiso 1 1 calc R U . . .
C4 C 0.97961(19) 0.78158(18) 0.40532(15) 0.0291(3) Uani 1 1 d . . . . .
H4 H 1.091551 0.761110 0.409029 0.035 Uiso 1 1 calc R U . . .
C5 C 0.90477(18) 0.88725(17) 0.31076(15) 0.0258(3) Uani 1 1 d . . . . .
C6 C 0.73788(18) 0.91538(17) 0.30851(15) 0.0270(3) Uani 1 1 d . . . . .
C7 C 0.65646(19) 1.02238(19) 0.21192(17) 0.0324(4) Uani 1 1 d . . . . .
C8 C 1.14436(18) 0.97018(18) 0.21105(16) 0.0294(4) Uani 1 1 d . . . . .
C9 C 1.1925(2) 1.0122(2) 0.3292(2) 0.0426(5) Uani 1 1 d . . . . .
H9A H 1.111510 1.089260 0.352376 0.064 Uiso 1 1 calc R U . . .
H9B H 1.293537 1.043820 0.313552 0.064 Uiso 1 1 calc R U . . .
H9C H 1.203642 0.930767 0.397970 0.064 Uiso 1 1 calc R U . . .
C10 C 1.1524(2) 1.0880(2) 0.0997(2) 0.0426(5) Uani 1 1 d . . . . .
H10A H 1.107006 1.066714 0.026348 0.064 Uiso 1 1 calc R U . . .
H10B H 1.262786 1.095951 0.080937 0.064 Uiso 1 1 calc R U . . .
H10C H 1.092549 1.177433 0.119965 0.064 Uiso 1 1 calc R U . . .
C11 C 1.2402(2) 0.8323(2) 0.18244(19) 0.0409(4) Uani 1 1 d . . . . .
H11A H 1.240003 0.758121 0.256666 0.061 Uiso 1 1 calc R U . . .
H11B H 1.349032 0.843378 0.160118 0.061 Uiso 1 1 calc R U . . .
H11C H 1.193810 0.806042 0.111998 0.061 Uiso 1 1 calc R U . . .
C12 C 0.32667(19) 0.67052(19) 0.66170(15) 0.0301(4) Uani 1 1 d . . . . .
C13 C 0.26322(18) 0.49871(17) 0.84318(15) 0.0269(3) Uani 1 1 d . . . . .
C14 C 0.1170(2) 0.4730(2) 0.78821(19) 0.0415(4) Uani 1 1 d . . . . .
H14A H 0.045981 0.563660 0.760618 0.062 Uiso 1 1 calc R U . . .
H14B H 0.062853 0.413785 0.852232 0.062 Uiso 1 1 calc R U . . .
H14C H 0.147382 0.425046 0.716184 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2265(2) 0.6030(2) 0.93177(18) 0.0422(4) Uani 1 1 d . . . . .
H15A H 0.325246 0.618758 0.961339 0.063 Uiso 1 1 calc R U . . .
H15B H 0.163915 0.565528 1.003774 0.063 Uiso 1 1 calc R U . . .
H15C H 0.166374 0.692644 0.887891 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3623(2) 0.3603(2) 0.9052(2) 0.0443(5) Uani 1 1 d . . . . .
H16A H 0.380094 0.293248 0.846640 0.066 Uiso 1 1 calc R U . . .
H16B H 0.306827 0.321302 0.980984 0.066 Uiso 1 1 calc R U . . .
H16C H 0.464031 0.376608 0.928251 0.066 Uiso 1 1 calc R U . . .
F1A F 0.7008(10) 0.6339(12) 0.7245(5) 0.0387(17) Uani 0.53(2) 1 d D . P A 1
O4A O 0.6483(15) 0.5034(12) 0.5646(12) 0.0352(17) Uani 0.53(2) 1 d . . P A 1
F1B F 0.6737(15) 0.4817(13) 0.5827(13) 0.043(2) Uani 0.47(2) 1 d . . P A 2
O4B O 0.6892(15) 0.6288(19) 0.7209(7) 0.058(4) Uani 0.47(2) 1 d D . P A 2


_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 N2 1.4986(14) . ?
S1 C2 1.7366(17) . ?
S1 F1A 1.517(5) . ?
S1 O4A 1.423(10) . ?
S1 F1B 1.557(12) . ?
S1 O4B 1.4240(10) . ?
O1 C5 1.3355(19) . ?
O1 C8 1.4816(18) . ?
O2 C12 1.200(2) . ?
O3 C12 1.339(2) . ?
O3 C13 1.4821(18) . ?
N1 C7 1.145(2) . ?
N2 C12 1.402(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C1 C6 1.390(2) . ?
C2 C3 1.394(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(2) . ?
C5 C6 1.415(2) . ?
C6 C7 1.441(2) . ?
C8 C9 1.520(3) . ?
C8 C10 1.518(2) . ?
C8 C11 1.512(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.514(2) . ?
C13 C15 1.505(3) . ?
C13 C16 1.514(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
N2 S1 C2 105.19(8) . . ?
N2 S1 F1A 117.8(3) . . ?
N2 S1 F1B 120.3(5) . . ?
F1A S1 C2 104.3(5) . . ?
O4A S1 N2 111.4(5) . . ?
O4A S1 C2 104.0(6) . . ?
O4A S1 F1A 112.6(7) . . ?
F1B S1 C2 106.3(5) . . ?
O4B S1 N2 116.2(5) . . ?
O4B S1 C2 107.9(7) . . ?
O4B S1 F1B 100.2(9) . . ?
C5 O1 C8 124.39(12) . . ?
C12 O3 C13 120.89(12) . . ?
C12 N2 S1 124.93(12) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.87(14) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 S1 120.84(12) . . ?
C1 C2 C3 120.64(15) . . ?
C3 C2 S1 118.52(13) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.57(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.28(15) . . ?
C5 C4 H4 119.9 . . ?
O1 C5 C4 127.12(14) . . ?
O1 C5 C6 114.55(14) . . ?
C4 C5 C6 118.32(14) . . ?
C1 C6 C5 121.32(14) . . ?
C1 C6 C7 118.67(14) . . ?
C5 C6 C7 120.01(14) . . ?
N1 C7 C6 176.56(18) . . ?
O1 C8 C9 110.02(13) . . ?
O1 C8 C10 101.78(13) . . ?
O1 C8 C11 110.44(14) . . ?
C10 C8 C9 109.67(16) . . ?
C11 C8 C9 114.21(15) . . ?
C11 C8 C10 110.01(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 126.54(15) . . ?
O2 C12 N2 121.51(15) . . ?
O3 C12 N2 111.95(14) . . ?
O3 C13 C14 111.04(13) . . ?
O3 C13 C15 108.52(14) . . ?
O3 C13 C16 101.85(12) . . ?
C14 C13 C16 110.43(16) . . ?
C15 C13 C14 113.02(15) . . ?
C15 C13 C16 111.41(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 N2 C12 O2 175.47(15) . . . . ?
S1 N2 C12 O3 -4.5(2) . . . . ?
S1 C2 C3 C4 179.47(13) . . . . ?
O1 C5 C6 C1 179.07(15) . . . . ?
O1 C5 C6 C7 -0.3(2) . . . . ?
N2 S1 C2 C1 -10.94(17) . . . . ?
N2 S1 C2 C3 169.81(14) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 S1 N2 C12 -178.38(15) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 179.19(16) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 O1 -178.64(16) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C4 C5 C6 C7 -179.38(16) . . . . ?
C5 O1 C8 C9 -56.8(2) . . . . ?
C5 O1 C8 C10 -172.98(15) . . . . ?
C5 O1 C8 C11 70.2(2) . . . . ?
C6 C1 C2 S1 -179.15(13) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C8 O1 C5 C4 -9.9(3) . . . . ?
C8 O1 C5 C6 171.10(14) . . . . ?
C12 O3 C13 C14 60.3(2) . . . . ?
C12 O3 C13 C15 -64.52(19) . . . . ?
C12 O3 C13 C16 177.86(16) . . . . ?
C13 O3 C12 O2 -9.5(3) . . . . ?
C13 O3 C12 N2 170.50(14) . . . . ?
F1A S1 N2 C12 -62.8(6) . . . . ?
F1A S1 C2 C1 -135.5(3) . . . . ?
F1A S1 C2 C3 45.3(4) . . . . ?
O4A S1 N2 C12 69.6(6) . . . . ?
O4A S1 C2 C1 106.3(5) . . . . ?
O4A S1 C2 C3 -72.9(5) . . . . ?
F1B S1 N2 C12 61.9(6) . . . . ?
F1B S1 C2 C1 117.7(6) . . . . ?
F1B S1 C2 C3 -61.6(6) . . . . ?
O4B S1 N2 C12 -59.1(9) . . . . ?
O4B S1 C2 C1 -135.6(7) . . . . ?
O4B S1 C2 C3 45.2(7) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_50
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.821
####################################################################### 
# 
# 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_en12950-96_100k
_database_code_depnum_ccdc_archive 'CCDC 2517072'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-12-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H41 N5 O6 S2, 1.5(C2 H6 O S)'
_chemical_formula_sum            'C38 H50 N5 O7.50 S3.50'
_chemical_formula_weight         809.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.2490(4)
_cell_length_b                   17.0030(3)
_cell_length_c                   18.6346(2)
_cell_angle_alpha                77.3590(10)
_cell_angle_beta                 83.203(2)
_cell_angle_gamma                70.348(2)
_cell_volume                     4143.76(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34686
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.2550
_cell_measurement_theta_min      2.8130
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.790
_exptl_absorpt_coefficient_mu    2.316
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1716
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -5 0.0363
5 2 0 0.0255
-5 -2 -1 0.0279
-2 -1 5 0.0487
2 2 5 0.0662
0 1 0 0.0055
0 -1 0 0.0212
-5 -1 5 0.0441
-1 -5 -4 0.0359

_exptl_crystal_preparation       
'The material was recrystallized from DMSO by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow evaporation'
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0017 -0.9901 -5.0046 0.0870 -0.1605 0.3749
5.0018 2.0039 0.0011 0.0899 -0.5103 -0.1680
-5.0013 -2.0024 -1.0013 -0.0915 0.4739 0.2446
-2.0035 -1.0086 5.0046 -0.0091 0.3910 -0.3180
2.0008 1.9881 5.0043 -0.0696 -0.0482 -0.4404
-0.0012 0.9991 -0.0000 -0.0951 -0.0218 0.0086
0.0012 -0.9991 0.0000 0.0951 0.0218 -0.0086
-5.0082 -1.0045 5.0053 -0.1780 0.6711 -0.2068
-0.9974 -4.9938 -4.0045 0.4134 0.0569 0.3010

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1405
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            102932
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.498
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_min         2.433
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  39.00   0.50    3.79    --   50.70 -34.00   8.00  134
  2  ω     31.00 130.00   0.50    3.79    --   50.70  34.00 166.00  198
  3  ω   -130.00 -31.00   0.50    3.79    --  -51.20 -34.00   8.00  198
  4  ω    -39.00  28.00   0.50    3.79    --  -51.20  34.00 166.00  134
  5  ω    -39.00  -1.00   0.50   11.53    --  -79.95  34.00 166.00   76
  6  ω   -159.00 -60.00   0.50   11.53    --  -79.95 -34.00   8.00  198
  7  ω     77.00 176.00   0.50   11.53    --   96.59  34.00 166.00  198
  8  ω     88.00 178.00   0.50   11.53    --  108.39  34.00 166.00  180
  9  ω    -65.00 -36.00   0.50    3.79    --   12.00 171.00 -90.83   58
 10  ω     -7.00  22.00   0.50    3.79    --   32.00  97.00-149.61   58
 11  ω      2.00  29.00   0.50    3.79    --   36.00  90.00 -29.30   54
 12  ω      1.00  27.00   0.50    3.79    --   36.00  92.00-139.76   52
 13  ω    -71.00  -5.00   0.50   11.53    --  -79.95  61.00   0.00  132
 14  ω    -35.00   0.00   0.50   11.53    --  -79.95  30.00 -90.00   70
 15  ω    -35.00   0.00   0.50   11.53    --  -79.95  30.00 120.00   70
 16  ω    -35.00   0.00   0.50   11.53    --  -79.95  30.00 -30.00   70
 17  ω   -159.00 -68.00   0.50   11.53    --  -88.50 -72.00 -43.90  182
 18  ω     19.00  51.00   0.50   11.53    --   96.59 -45.00 -60.00   64
 19  ω     28.00 105.00   0.50   11.53    --   96.59 -95.00-180.00  154
 20  ω     19.00  51.00   0.50   11.53    --   96.59 -45.00-180.00   64
 21  ω     22.00  71.00   0.50   11.53    --   96.59 -61.00   0.00   98
 22  ω     19.00  51.00   0.50   11.53    --   96.59 -45.00  30.00   64
 23  ω     19.00  51.00   0.50   11.53    --   96.59 -45.00 -30.00   64
 24  ω     19.00  51.00   0.50   11.53    --   96.59 -45.00 150.00   64
 25  ω     34.00 112.00   0.50   11.53    --   96.59-125.00 120.00  156
 26  ω     19.00  51.00   0.50   11.53    --   96.59 -45.00 -90.00   64
 27  ω     95.00 171.00   0.50   11.53    --   96.59 125.00  30.00  152
 28  ω     28.00 105.00   0.50   11.53    --   96.59 -95.00 -30.00  154
 29  ω     28.00 105.00   0.50   11.53    --   96.59 -95.00 120.00  154
 30  ω     32.00 106.00   0.50   11.53    --  102.49 -99.00 116.46  148
 31  ω     40.00 105.00   0.50   11.53    --  108.39 -95.00 150.00  130
 32  ω     92.00 178.00   0.50   11.53    --  108.39  45.00  30.00  172
 33  ω     40.00 105.00   0.50   11.53    --  108.39 -95.00-120.00  130
 34  ω     34.00  71.00   0.50   11.53    --  108.39 -61.00 150.00   74
 35  ω     34.00  71.00   0.50   11.53    --  108.39 -61.00-180.00   74
 36  ω     34.00  71.00   0.50   11.53    --  108.39 -61.00  30.00   74
 37  ω     34.00  71.00   0.50   11.53    --  108.39 -61.00-150.00   74
 38  ω     34.00 112.00   0.50   11.53    --  108.39-125.00 150.00  156
 39  ω     34.00 112.00   0.50   11.53    --  108.39-125.00   0.00  156
 40  ω     40.00 105.00   0.50   11.53    --  108.39 -95.00   0.00  130
 41  ω     16.00  43.00   0.50    3.79    --   44.00  79.00   4.10   54
 42  ω     17.00  43.00   0.50    3.79    --   44.00  78.00 -63.69   52
 43  ω     17.00  43.00   0.50    3.79    --   44.00  78.00  55.84   52
 44  ω     16.00  43.00   0.50    3.79    --   44.00  79.00 111.19   54
 45  ω     40.00 135.00   0.50    3.79    --   64.00  72.00 -79.03  190
 46  ω     41.00 135.00   0.50    3.79    --   64.00  71.00-143.69  188
 47  ω   -139.00 -44.00   0.50    3.79    --  -68.00 -72.00 128.45  190
 48  ω   -155.00 -61.00   0.50   11.53    --  -84.00 -70.00  33.99  188
 49  ω   -155.00 -60.00   0.50   11.53    --  -84.00 -71.00-173.51  190
 50  ω   -156.00 -61.00   0.50   11.53    --  -84.00 -68.00  90.11  190
 51  ω   -155.00 -60.00   0.50   11.53    --  -84.00 -71.00  -7.34  190
 52  ω   -160.00 -65.00   0.50   11.53    --  -88.50 -70.00-140.17  190
 53  ω   -159.00 -65.00   0.50   11.53    --  -88.50 -71.00 -79.05  188
 54  ω   -159.00 -65.00   0.50   11.53    --  -88.50 -71.00-108.29  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0560922000
_diffrn_orient_matrix_UB_12      -0.0951560000
_diffrn_orient_matrix_UB_13      0.0014627000
_diffrn_orient_matrix_UB_21      -0.0932550000
_diffrn_orient_matrix_UB_22      -0.0219223000
_diffrn_orient_matrix_UB_23      0.0363693000
_diffrn_orient_matrix_UB_31      -0.0369961000
_diffrn_orient_matrix_UB_32      0.0085546000
_diffrn_orient_matrix_UB_33      -0.0766205000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11668
_reflns_number_total             14937
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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  (Sheldrick, 2015)'
_refine_diff_density_max         0.746
_refine_diff_density_min         -1.155
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1068
_refine_ls_number_reflns         14937
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0855
_refine_ls_restrained_S_all      1.041
_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)+(0.1464P)²+4.2234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2417
_refine_ls_wR_factor_ref         0.2540
_refine_special_details          
'This structure should be only used to confirm chemical connectivity because the data quality is poor; H atom in N2, N5, N6 and N10 were calculated and not found from the difference of Fourier map, however this positions are rationalized because the existance of hydrogen bonding to adjacent atoms that are acceptor hydrogen bond; There is a void in the crystal structure;  DMSO molecule containing S5 was refined as disorder with occupancy approximately 0.80: 0.20; DMSO molecule containing S7 was refined as disorder with occupancy approximately 0.76: 0.24'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H70A,H70B,H70C} of C70, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  {H33A,H33B,H33C} of C33, {H45A,H45B,H45C} of C45, {H49A,H49B,H49C} of C49,
  {H50A,H50B,H50C} of C50, {H35A,H35B,H35C} of C35, {H34A,H34B,H34C} of C34,
  {H10A,H10B,H10C} of C10, {H15A,H15B,H15C} of C15, {H14A,H14B,H14C} of C14,
  {H74A,H74B,H74C} of C74, {H76A,H76B,H76C} of C76A, {H76D,H76E,H76F} of C76B,
  {H77A,H77B,H77C} of C77A, {H77D,H77E,H77F} of C77B, {H72A,H72B,H72C} of C72A,
  {H73A,H73B,H73C} of C73, {H69A,H69B,H69C} of C69, {H51A,H51B,H51C} of C51,
  {H72D,H72E,H72F} of C72B, {H68A,H68B,H68C} of C68, {H71D,H71E,H71F} of C71B,
  {H71A,H71B,H71C} of C71A, {H16A,H16B,H16C} of C16
2. Restrained distances
 S5A-O13A \\sim S5B-O13B
 with sigma of 0.02
 S5A-C72A \\sim S5B-C71B
 with sigma of 0.02
 S5A-C71A \\sim S5B-C72B
 with sigma of 0.02
 O13A-C72A \\sim O13B-C71B
 with sigma of 0.04
 O13A-C71A \\sim O13B-C72B
 with sigma of 0.04
 C72A-C71A \\sim C71B-C72B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
S5B \\sim O13B \\sim C71B \\sim C72B: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
4. Rigid body (RIGU) restrains
 S7B, O15B, C76B, C77B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S7B)=Sof(O15B)=Sof(C76B)=Sof(H76D)=Sof(H76E)=Sof(H76F)=Sof(C77B)=
 Sof(H77D)=Sof(H77E)=Sof(H77F)=1-FVAR(1)
 Sof(S7A)=Sof(O15A)=Sof(C76A)=Sof(H76A)=Sof(H76B)=Sof(H76C)=Sof(C77A)=
 Sof(H77A)=Sof(H77B)=Sof(H77C)=FVAR(1)
 Sof(S5B)=Sof(O13B)=Sof(C71B)=Sof(H71D)=Sof(H71E)=Sof(H71F)=Sof(C72B)=
 Sof(H72D)=Sof(H72E)=Sof(H72F)=1-FVAR(2)
 Sof(S5A)=Sof(O13A)=Sof(C71A)=Sof(H71A)=Sof(H71B)=Sof(H71C)=Sof(C72A)=
 Sof(H72A)=Sof(H72B)=Sof(H72C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C58(H58A,H58B), C59(H59A,H59B)
6.b Me refined with riding coordinates:
 C71B(H71D,H71E,H71F), C72B(H72D,H72E,H72F), C77B(H77D,H77E,H77F)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5A), C8(H8), C18(H18),
 C19(H19), C20(H20), C21(H21), C26(H26), C27(H27), C28(H28), C29(H29), N6(H6),
 N10(H10), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C43(H43), C53(H53),
  C54(H54), C55(H55), C56(H56), C61(H61), C62(H62), C63(H63), C64(H64)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C45(H45A,
 H45B,H45C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C),
 C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C71A(H71A,H71B,
 H71C), C72A(H72A,H72B,H72C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C),
 C76A(H76A,H76B,H76C), C76B(H76D,H76E,H76F), C77A(H77A,H77B,H77C)
;
_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 0.99575(8) 0.27116(7) 0.31992(6) 0.0524(3) Uani 1 1 d . . . . .
S2 S 0.48516(9) 0.40089(7) 0.36944(6) 0.0552(3) Uani 1 1 d . . . . .
O1 O 1.0902(2) 0.2257(2) 0.28782(18) 0.0602(8) Uani 1 1 d . . . . .
O2 O 0.9048(4) 0.4744(2) 0.1917(2) 0.0901(13) Uani 1 1 d . . . . .
O3 O 0.9478(2) 0.3379(2) 0.17992(17) 0.0582(7) Uani 1 1 d . . . . .
O4 O 0.4123(3) 0.4007(2) 0.43280(19) 0.0715(9) Uani 1 1 d . . . . .
O5 O 0.4093(3) 0.3243(2) 0.27506(18) 0.0624(8) Uani 1 1 d . . . . .
O6 O 0.3241(2) 0.45343(19) 0.20884(16) 0.0577(8) Uani 1 1 d . . . . .
N1 N 1.0666(3) 0.1184(2) 0.42825(19) 0.0489(8) Uani 1 1 d . . . . .
N2 N 1.0337(3) 0.1970(2) 0.5227(2) 0.0521(8) Uani 1 1 d . . . . .
H2 H 1.011530 0.246947 0.536018 0.063 Uiso 1 1 calc R U . . .
N3 N 0.9943(3) 0.2685(3) 0.4062(2) 0.0550(9) Uani 1 1 d . . . . .
N4 N 0.9551(3) 0.3693(2) 0.2920(2) 0.0570(9) Uani 1 1 d . . . . .
N5 N 0.4234(3) 0.4489(2) 0.2923(2) 0.0565(9) Uani 1 1 d . . . . .
H5 H 0.414953 0.502829 0.273350 0.068 Uiso 1 1 calc R U . . .
C1 C 1.1512(3) -0.0295(3) 0.3742(2) 0.0504(9) Uani 1 1 d . . . . .
H1 H 1.135653 0.023935 0.341422 0.061 Uiso 1 1 calc R U . . .
C2 C 1.1842(3) -0.1034(3) 0.3465(2) 0.0548(10) Uani 1 1 d . . . . .
H2A H 1.190465 -0.100413 0.294729 0.066 Uiso 1 1 calc R U . . .
C3 C 1.2084(4) -0.1821(3) 0.3934(3) 0.0593(11) Uani 1 1 d . . . . .
H3 H 1.231411 -0.233150 0.374303 0.071 Uiso 1 1 calc R U . . .
C4 C 1.1981(4) -0.1849(3) 0.4690(3) 0.0630(12) Uani 1 1 d . . . . .
H4 H 1.214360 -0.238340 0.501778 0.076 Uiso 1 1 calc R U . . .
C5 C 1.1650(4) -0.1118(3) 0.4968(2) 0.0566(11) Uani 1 1 d . . . . .
H5A H 1.158717 -0.115190 0.548581 0.068 Uiso 1 1 calc R U . . .
C6 C 1.1404(3) -0.0325(3) 0.4504(2) 0.0469(9) Uani 1 1 d . . . . .
C7 C 1.1029(3) 0.0476(3) 0.4784(2) 0.0480(9) Uani 1 1 d . . . . .
C8 C 1.1046(3) 0.0496(3) 0.5532(2) 0.0528(10) Uani 1 1 d . . . . .
H8 H 1.130536 -0.001283 0.588015 0.063 Uiso 1 1 calc R U . . .
C9 C 1.0683(3) 0.1262(3) 0.5744(2) 0.0516(10) Uani 1 1 d . . . . .
C10 C 1.0624(4) 0.1383(3) 0.6524(2) 0.0584(11) Uani 1 1 d . . . . .
H10A H 0.994256 0.145645 0.673285 0.088 Uiso 1 1 calc R U . . .
H10B H 1.080239 0.188957 0.653225 0.088 Uiso 1 1 calc R U . . .
H10C H 1.108783 0.088279 0.681498 0.088 Uiso 1 1 calc R U . . .
C11 C 1.0322(3) 0.1932(3) 0.4501(2) 0.0508(10) Uani 1 1 d . . . . .
C12 C 0.9349(4) 0.3984(3) 0.2193(3) 0.0611(11) Uani 1 1 d . . . . .
C13 C 0.9189(4) 0.3564(4) 0.1039(3) 0.0667(13) Uani 1 1 d . . . . .
C14 C 0.9394(6) 0.2683(4) 0.0869(4) 0.0891(18) Uani 1 1 d . . . . .
H14A H 0.921892 0.273819 0.036343 0.134 Uiso 1 1 calc R U . . .
H14B H 0.899168 0.238485 0.121219 0.134 Uiso 1 1 calc R U . . .
H14C H 1.010310 0.235849 0.092313 0.134 Uiso 1 1 calc R U . . .
C15 C 0.9860(6) 0.3997(4) 0.0547(3) 0.0920(19) Uani 1 1 d . . . . .
H15A H 1.055110 0.371239 0.069041 0.138 Uiso 1 1 calc R U . . .
H15B H 0.965505 0.459471 0.059690 0.138 Uiso 1 1 calc R U . . .
H15C H 0.981085 0.396742 0.003429 0.138 Uiso 1 1 calc R U . . .
C16 C 0.8076(5) 0.4050(6) 0.0989(4) 0.111(3) Uani 1 1 d . . . . .
H16A H 0.794493 0.462772 0.107168 0.167 Uiso 1 1 calc R U . . .
H16B H 0.770096 0.375625 0.136322 0.167 Uiso 1 1 calc R U . . .
H16C H 0.786614 0.407819 0.049874 0.167 Uiso 1 1 calc R U . . .
C17 C 0.9043(4) 0.2242(3) 0.3066(2) 0.0537(10) Uani 1 1 d . . . . .
C18 C 0.9421(4) 0.1502(3) 0.2778(3) 0.0616(12) Uani 1 1 d . . . . .
H18 H 1.011434 0.128122 0.265851 0.074 Uiso 1 1 calc R U . . .
C19 C 0.8768(4) 0.1085(3) 0.2665(3) 0.0675(13) Uani 1 1 d . . . . .
H19 H 0.901516 0.058380 0.246105 0.081 Uiso 1 1 calc R U . . .
C20 C 0.7774(4) 0.1404(3) 0.2852(3) 0.0668(13) Uani 1 1 d . . . . .
H20 H 0.733490 0.111382 0.278541 0.080 Uiso 1 1 calc R U . . .
C21 C 0.7401(4) 0.2134(3) 0.3134(3) 0.0635(12) Uani 1 1 d . . . . .
H21 H 0.670576 0.234421 0.325329 0.076 Uiso 1 1 calc R U . . .
C22 C 0.8028(3) 0.2581(3) 0.3250(3) 0.0546(10) Uani 1 1 d . . . . .
C23 C 0.7524(3) 0.3383(3) 0.3552(3) 0.0544(10) Uani 1 1 d . . . . .
H23A H 0.803751 0.356371 0.372188 0.065 Uiso 1 1 calc R U . . .
H23B H 0.708222 0.326081 0.398301 0.065 Uiso 1 1 calc R U . . .
C24 C 0.6904(4) 0.4115(3) 0.2980(3) 0.0603(11) Uani 1 1 d . . . . .
H24A H 0.735824 0.431746 0.259741 0.072 Uiso 1 1 calc R U . . .
H24B H 0.648108 0.390234 0.273756 0.072 Uiso 1 1 calc R U . . .
C25 C 0.6245(4) 0.4852(3) 0.3331(3) 0.0558(11) Uani 1 1 d . . . . .
C26 C 0.6564(4) 0.5545(3) 0.3337(3) 0.0721(14) Uani 1 1 d . . . . .
H26 H 0.719007 0.556317 0.310825 0.086 Uiso 1 1 calc R U . . .
C27 C 0.5958(5) 0.6214(3) 0.3683(3) 0.0741(16) Uani 1 1 d . . . . .
H27 H 0.618088 0.668167 0.368164 0.089 Uiso 1 1 calc R U . . .
C28 C 0.5062(5) 0.6203(3) 0.4017(3) 0.0756(15) Uani 1 1 d . . . . .
H28 H 0.465924 0.666414 0.424099 0.091 Uiso 1 1 calc R U . . .
C29 C 0.4740(4) 0.5527(3) 0.4032(3) 0.0665(13) Uani 1 1 d . . . . .
H29 H 0.412411 0.550594 0.427867 0.080 Uiso 1 1 calc R U . . .
C30 C 0.5326(4) 0.4872(3) 0.3680(3) 0.0577(11) Uani 1 1 d . . . . .
C31 C 0.3863(3) 0.4009(3) 0.2594(2) 0.0521(10) Uani 1 1 d . . . . .
C32 C 0.2722(4) 0.4201(4) 0.1647(3) 0.0723(14) Uani 1 1 d . . . . .
C33 C 0.3519(6) 0.3655(5) 0.1177(3) 0.094(2) Uani 1 1 d . . . . .
H33A H 0.395942 0.316764 0.149840 0.141 Uiso 1 1 calc R U . . .
H33B H 0.391210 0.399623 0.088007 0.141 Uiso 1 1 calc R U . . .
H33C H 0.319912 0.345116 0.085186 0.141 Uiso 1 1 calc R U . . .
C34 C 0.2094(5) 0.3722(5) 0.2122(4) 0.094(2) Uani 1 1 d . . . . .
H34A H 0.165970 0.407323 0.246023 0.140 Uiso 1 1 calc R U . . .
H34B H 0.252548 0.319489 0.240481 0.140 Uiso 1 1 calc R U . . .
H34C H 0.168336 0.358576 0.181122 0.140 Uiso 1 1 calc R U . . .
C35 C 0.2089(6) 0.5021(5) 0.1186(4) 0.113(3) Uani 1 1 d . . . . .
H35A H 0.171145 0.488694 0.084878 0.169 Uiso 1 1 calc R U . . .
H35B H 0.252250 0.533105 0.090104 0.169 Uiso 1 1 calc R U . . .
H35C H 0.162447 0.537373 0.151023 0.169 Uiso 1 1 calc R U . . .
S3 S 0.68119(7) 0.92781(6) 0.22591(5) 0.0402(2) Uani 1 1 d . . . . .
S4 S 0.35085(8) 0.71133(7) 0.22291(6) 0.0512(3) Uani 1 1 d . . . . .
S5A S 0.86151(12) 0.39489(10) 0.53552(12) 0.0740(7) Uani 0.798(5) 1 d D . P A 1
S5B S 0.8802(7) 0.4491(7) 0.5478(5) 0.099(3) Uani 0.202(5) 1 d D U P A 2
S6 S 0.88512(11) 0.66985(10) 0.29313(9) 0.0802(4) Uani 1 1 d . . . . .
S7A S 0.34475(11) 0.75301(10) -0.05553(8) 0.0557(5) Uani 0.765(4) 1 d . . P B 1
S7B S 0.3401(5) 0.8106(4) -0.0161(3) 0.077(2) Uani 0.235(4) 1 d . . P B 2
O7 O 0.72969(19) 0.99103(17) 0.22076(14) 0.0436(6) Uani 1 1 d . . . . .
O8 O 0.6482(2) 1.00095(18) 0.07181(15) 0.0493(7) Uani 1 1 d . . . . .
O9 O 0.7272(2) 0.86997(19) 0.04392(14) 0.0497(7) Uani 1 1 d . . . . .
O10 O 0.3361(3) 0.6296(2) 0.2594(2) 0.0675(9) Uani 1 1 d . . . . .
O11 O 0.1503(3) 0.8053(3) 0.22966(19) 0.0724(10) Uani 1 1 d . . . . .
O12 O 0.1319(2) 0.8305(3) 0.10658(19) 0.0765(11) Uani 1 1 d . . . . .
O13A O 0.9640(3) 0.3480(3) 0.5642(3) 0.0624(13) Uani 0.798(5) 1 d D . P A 1
O13B O 0.9685(16) 0.3758(17) 0.5379(16) 0.098(4) Uani 0.202(5) 1 d D U P A 2
O14 O 0.8146(3) 0.6513(2) 0.3581(2) 0.0709(9) Uani 1 1 d . . . . .
O15A O 0.3155(6) 0.7017(5) 0.0160(5) 0.0584(16) Uani 0.765(4) 1 d . . P B 1
O15B O 0.336(3) 0.720(3) 0.011(2) 0.115(14) Uani 0.235(4) 1 d . . P B 2
N6 N 0.7339(2) 0.7915(2) 0.41442(17) 0.0424(7) Uani 1 1 d . . . . .
H6 H 0.757936 0.741934 0.400501 0.051 Uiso 1 1 calc R U . . .
N7 N 0.6602(2) 0.94029(19) 0.38123(15) 0.0362(6) Uani 1 1 d . . . . .
N8 N 0.7112(2) 0.8494(2) 0.29316(17) 0.0433(7) Uani 1 1 d . . . . .
N9 N 0.7060(2) 0.8780(2) 0.16089(17) 0.0435(7) Uani 1 1 d . . . . .
N10 N 0.2794(3) 0.7545(2) 0.1501(2) 0.0576(9) Uani 1 1 d . . . . .
H10 H 0.302267 0.749466 0.104825 0.069 Uiso 1 1 calc R U . . .
C36 C 0.6068(3) 1.0468(3) 0.54043(19) 0.0443(9) Uani 1 1 d . . . . .
H36 H 0.636528 1.001619 0.579197 0.053 Uiso 1 1 calc R U . . .
C37 C 0.5622(3) 1.1276(3) 0.5543(2) 0.0478(9) Uani 1 1 d . . . . .
H37 H 0.562251 1.137795 0.602472 0.057 Uiso 1 1 calc R U . . .
C38 C 0.5171(3) 1.1944(3) 0.4991(2) 0.0475(9) Uani 1 1 d . . . . .
H38 H 0.486397 1.250143 0.509046 0.057 Uiso 1 1 calc R U . . .
C39 C 0.5173(3) 1.1790(3) 0.4289(2) 0.0477(9) Uani 1 1 d . . . . .
H39 H 0.485267 1.224076 0.390827 0.057 Uiso 1 1 calc R U . . .
C40 C 0.5636(3) 1.0987(2) 0.4144(2) 0.0436(9) Uani 1 1 d . . . . .
H40 H 0.564809 1.089257 0.365864 0.052 Uiso 1 1 calc R U . . .
C41 C 0.6090(3) 1.0305(2) 0.46977(18) 0.0364(7) Uani 1 1 d . . . . .
C42 C 0.6558(3) 0.9445(2) 0.45260(18) 0.0362(7) Uani 1 1 d . . . . .
C43 C 0.6924(3) 0.8714(3) 0.5070(2) 0.0430(8) Uani 1 1 d . . . . .
H43 H 0.689845 0.875862 0.557159 0.052 Uiso 1 1 calc R U . . .
C44 C 0.7315(3) 0.7943(3) 0.4867(2) 0.0434(8) Uani 1 1 d . . . . .
C45 C 0.7707(4) 0.7112(3) 0.5378(2) 0.0538(10) Uani 1 1 d . . . . .
H45A H 0.776813 0.721367 0.586571 0.081 Uiso 1 1 calc R U . . .
H45B H 0.836305 0.679142 0.518840 0.081 Uiso 1 1 calc R U . . .
H45C H 0.724647 0.678546 0.541657 0.081 Uiso 1 1 calc R U . . .
C46 C 0.6999(3) 0.8639(2) 0.36240(19) 0.0382(8) Uani 1 1 d . . . . .
C47 C 0.6889(3) 0.9253(3) 0.0910(2) 0.0427(9) Uani 1 1 d . . . . .
C48 C 0.7114(3) 0.8971(3) -0.0358(2) 0.0479(9) Uani 1 1 d . . . . .
C49 C 0.7650(4) 0.9593(5) -0.0704(3) 0.0764(16) Uani 1 1 d . . . . .
H49A H 0.735276 1.011805 -0.050802 0.115 Uiso 1 1 calc R U . . .
H49B H 0.759062 0.972136 -0.123840 0.115 Uiso 1 1 calc R U . . .
H49C H 0.835560 0.934666 -0.059013 0.115 Uiso 1 1 calc R U . . .
C50 C 0.6012(3) 0.9323(3) -0.0491(2) 0.0510(10) Uani 1 1 d . . . . .
H50A H 0.567797 0.892731 -0.020546 0.077 Uiso 1 1 calc R U . . .
H50B H 0.591368 0.939586 -0.101580 0.077 Uiso 1 1 calc R U . . .
H50C H 0.572877 0.987459 -0.033670 0.077 Uiso 1 1 calc R U . . .
C51 C 0.7564(4) 0.8129(4) -0.0622(3) 0.0795(18) Uani 1 1 d . . . . .
H51A H 0.826211 0.787324 -0.049032 0.119 Uiso 1 1 calc R U . . .
H51B H 0.752849 0.823000 -0.115829 0.119 Uiso 1 1 calc R U . . .
H51C H 0.718971 0.774281 -0.038868 0.119 Uiso 1 1 calc R U . . .
C52 C 0.5493(3) 0.9796(2) 0.23585(19) 0.0398(8) Uani 1 1 d . . . . .
C53 C 0.5188(3) 1.0662(2) 0.23770(19) 0.0421(8) Uani 1 1 d . . . . .
H53 H 0.566955 1.094900 0.230946 0.051 Uiso 1 1 calc R U . . .
C54 C 0.4192(3) 1.1104(3) 0.2493(2) 0.0462(9) Uani 1 1 d . . . . .
H54 H 0.398568 1.169476 0.250215 0.055 Uiso 1 1 calc R U . . .
C55 C 0.3496(3) 1.0680(3) 0.2595(2) 0.0466(9) Uani 1 1 d . . . . .
H55 H 0.281024 1.097499 0.268461 0.056 Uiso 1 1 calc R U . . .
C56 C 0.3807(3) 0.9822(3) 0.25662(19) 0.0457(9) Uani 1 1 d . . . . .
H56 H 0.332095 0.954025 0.263232 0.055 Uiso 1 1 calc R U . . .
C57 C 0.4798(3) 0.9358(3) 0.24447(19) 0.0418(8) Uani 1 1 d . . . . .
C58 C 0.5074(3) 0.8426(3) 0.2391(2) 0.0441(9) Uani 1 1 d . . . . .
H58A H 0.471363 0.813808 0.279238 0.053 Uiso 1 1 calc R U . . .
H58B H 0.579829 0.814512 0.245239 0.053 Uiso 1 1 calc R U . . .
C59 C 0.4803(3) 0.8339(3) 0.1641(2) 0.0456(9) Uani 1 1 d . . . . .
H59A H 0.406797 0.854608 0.161594 0.055 Uiso 1 1 calc R U . . .
H59B H 0.507367 0.870790 0.124462 0.055 Uiso 1 1 calc R U . . .
C60 C 0.5196(3) 0.7439(3) 0.1501(2) 0.0473(9) Uani 1 1 d . . . . .
C61 C 0.6126(4) 0.7168(3) 0.1151(2) 0.0567(11) Uani 1 1 d . . . . .
H61 H 0.651617 0.753901 0.102805 0.068 Uiso 1 1 calc R U . . .
C62 C 0.6499(4) 0.6360(3) 0.0975(3) 0.0639(12) Uani 1 1 d . . . . .
H62 H 0.714240 0.618349 0.073750 0.077 Uiso 1 1 calc R U . . .
C63 C 0.5934(4) 0.5812(3) 0.1146(3) 0.0667(13) Uani 1 1 d . . . . .
H63 H 0.617865 0.527079 0.100668 0.080 Uiso 1 1 calc R U . . .
C64 C 0.5021(4) 0.6052(3) 0.1515(3) 0.0571(11) Uani 1 1 d . . . . .
H64 H 0.464170 0.567257 0.164692 0.069 Uiso 1 1 calc R U . . .
C65 C 0.4654(3) 0.6861(3) 0.1696(2) 0.0484(9) Uani 1 1 d . . . . .
C66 C 0.1830(4) 0.7979(3) 0.1669(3) 0.0619(12) Uani 1 1 d . . . . .
C67 C 0.0234(4) 0.8692(5) 0.1138(4) 0.0889(19) Uani 1 1 d . . . . .
C68 C -0.0035(5) 0.9483(5) 0.1467(3) 0.092(2) Uani 1 1 d . . . . .
H68A H -0.075749 0.976948 0.145607 0.138 Uiso 1 1 calc R U . . .
H68B H 0.031109 0.986889 0.118016 0.138 Uiso 1 1 calc R U . . .
H68C H 0.016660 0.932405 0.197738 0.138 Uiso 1 1 calc R U . . .
C69 C -0.0193(5) 0.8019(6) 0.1572(5) 0.118(3) Uani 1 1 d . . . . .
H69A H 0.003554 0.785306 0.207541 0.177 Uiso 1 1 calc R U . . .
H69B H 0.003107 0.752069 0.133638 0.177 Uiso 1 1 calc R U . . .
H69C H -0.092351 0.824648 0.158564 0.177 Uiso 1 1 calc R U . . .
C70 C -0.0053(6) 0.8926(8) 0.0343(5) 0.152(5) Uani 1 1 d . . . . .
H70A H 0.028292 0.932177 0.006211 0.182 Uiso 1 1 calc R U . . .
H70B H -0.077752 0.919613 0.032105 0.182 Uiso 1 1 calc R U . . .
H70C H 0.014858 0.841024 0.013196 0.182 Uiso 1 1 calc R U . . .
C71A C 0.7999(6) 0.4652(5) 0.5947(6) 0.094(3) Uani 0.798(5) 1 d D . P A 1
H71A H 0.781405 0.433264 0.641528 0.140 Uiso 0.798(5) 1 calc R U P A 1
H71B H 0.739527 0.506617 0.572107 0.140 Uiso 0.798(5) 1 calc R U P A 1
H71C H 0.844065 0.495135 0.603548 0.140 Uiso 0.798(5) 1 calc R U P A 1
C71B C 0.832(3) 0.441(3) 0.6383(12) 0.100(4) Uani 0.202(5) 1 d D U P A 2
H71D H 0.773440 0.491048 0.642468 0.150 Uiso 0.202(5) 1 calc R U P A 2
H71E H 0.812556 0.389517 0.652719 0.150 Uiso 0.202(5) 1 calc R U P A 2
H71F H 0.882827 0.438198 0.670820 0.150 Uiso 0.202(5) 1 calc R U P A 2
C72A C 0.8795(7) 0.4699(5) 0.4572(5) 0.091(3) Uani 0.798(5) 1 d D . P A 1
H72A H 0.916438 0.503515 0.470597 0.137 Uiso 0.798(5) 1 calc R U P A 1
H72B H 0.814586 0.507786 0.439355 0.137 Uiso 0.798(5) 1 calc R U P A 1
H72C H 0.917597 0.439929 0.418370 0.137 Uiso 0.798(5) 1 calc R U P A 1
C72B C 0.786(2) 0.458(2) 0.4930(17) 0.099(4) Uani 0.202(5) 1 d D U P A 2
H72D H 0.728571 0.507350 0.500621 0.149 Uiso 0.202(5) 1 calc R U P A 2
H72E H 0.810207 0.465832 0.441233 0.149 Uiso 0.202(5) 1 calc R U P A 2
H72F H 0.767255 0.406401 0.506043 0.149 Uiso 0.202(5) 1 calc R U P A 2
C73 C 0.9852(5) 0.5727(6) 0.2945(5) 0.125(3) Uani 1 1 d . . . . .
H73A H 1.021369 0.559036 0.339546 0.188 Uiso 1 1 calc R U . . .
H73B H 1.030783 0.578779 0.251477 0.188 Uiso 1 1 calc R U . . .
H73C H 0.958619 0.526897 0.293222 0.188 Uiso 1 1 calc R U . . .
C74 C 0.8297(5) 0.6708(4) 0.2113(4) 0.0827(17) Uani 1 1 d . . . . .
H74A H 0.807583 0.620788 0.218434 0.124 Uiso 1 1 calc R U . . .
H74B H 0.878877 0.669549 0.169771 0.124 Uiso 1 1 calc R U . . .
H74C H 0.772220 0.722581 0.201049 0.124 Uiso 1 1 calc R U . . .
C76A C 0.2455(7) 0.8516(8) -0.0714(7) 0.058(2) Uani 0.765(4) 1 d . . P B 1
H76A H 0.186594 0.842029 -0.085366 0.087 Uiso 0.765(4) 1 calc R U P B 1
H76B H 0.266102 0.891612 -0.111106 0.087 Uiso 0.765(4) 1 calc R U P B 1
H76C H 0.229173 0.875293 -0.026295 0.087 Uiso 0.765(4) 1 calc R U P B 1
C76B C 0.272(3) 0.851(4) -0.088(3) 0.087(13) Uani 0.235(4) 1 d . . P B 2
H76D H 0.302125 0.888722 -0.124050 0.130 Uiso 0.235(4) 1 calc R U P B 2
H76E H 0.204581 0.884458 -0.073196 0.130 Uiso 0.235(4) 1 calc R U P B 2
H76F H 0.268644 0.805561 -0.110825 0.130 Uiso 0.235(4) 1 calc R U P B 2
C77A C 0.4351(5) 0.7927(5) -0.0339(4) 0.0556(17) Uani 0.765(4) 1 d . . P B 1
H77A H 0.410029 0.821386 0.008114 0.083 Uiso 0.765(4) 1 calc R U P B 1
H77B H 0.448898 0.833379 -0.076465 0.083 Uiso 0.765(4) 1 calc R U P B 1
H77C H 0.496609 0.745582 -0.021213 0.083 Uiso 0.765(4) 1 calc R U P B 1
C77B C 0.460(2) 0.783(3) -0.063(2) 0.099(12) Uani 0.235(4) 1 d . . P B 2
H77D H 0.475992 0.835108 -0.085559 0.149 Uiso 0.235(4) 1 calc R U P B 2
H77E H 0.510146 0.746523 -0.028618 0.149 Uiso 0.235(4) 1 calc R U P B 2
H77F H 0.458281 0.752879 -0.102235 0.149 Uiso 0.235(4) 1 calc R U P B 2


_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 1.441(4) . ?
S1 N3 1.596(4) . ?
S1 N4 1.559(4) . ?
S1 C17 1.805(4) . ?
S2 O4 1.477(4) . ?
S2 N5 1.677(4) . ?
S2 C30 1.805(5) . ?
O2 C12 1.228(6) . ?
O3 C12 1.342(6) . ?
O3 C13 1.461(6) . ?
O5 C31 1.207(5) . ?
O6 C31 1.329(5) . ?
O6 C32 1.476(6) . ?
N1 C7 1.339(6) . ?
N1 C11 1.336(6) . ?
N2 H2 0.8800 . ?
N2 C9 1.351(6) . ?
N2 C11 1.372(6) . ?
N3 C11 1.336(6) . ?
N4 C12 1.366(6) . ?
N5 H5 0.8800 . ?
N5 C31 1.381(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.376(6) . ?
C1 C6 1.402(6) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(7) . ?
C5 H5A 0.9500 . ?
C5 C6 1.389(6) . ?
C6 C7 1.472(6) . ?
C7 C8 1.405(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.358(7) . ?
C9 C10 1.500(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13 C14 1.523(8) . ?
C13 C15 1.506(8) . ?
C13 C16 1.525(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.390(6) . ?
C17 C22 1.396(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.403(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.368(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.368(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.414(6) . ?
C22 C23 1.508(7) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.539(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.517(7) . ?
C25 C26 1.400(7) . ?
C25 C30 1.385(7) . ?
C26 H26 0.9500 . ?
C26 C27 1.408(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.357(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.367(8) . ?
C29 H29 0.9500 . ?
C29 C30 1.389(7) . ?
C32 C33 1.526(9) . ?
C32 C34 1.494(8) . ?
C32 C35 1.520(8) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
S3 O7 1.443(3) . ?
S3 N8 1.594(3) . ?
S3 N9 1.568(3) . ?
S3 C52 1.794(4) . ?
S4 O10 1.478(3) . ?
S4 N10 1.675(4) . ?
S4 C65 1.779(5) . ?
S5A O13A 1.506(4) . ?
S5A C71A 1.749(9) . ?
S5A C72A 1.772(8) . ?
S5B O13B 1.470(17) . ?
S5B C71B 1.738(19) . ?
S5B C72B 1.722(17) . ?
S6 O14 1.527(4) . ?
S6 C73 1.780(7) . ?
S6 C74 1.793(6) . ?
S7A O15A 1.521(8) . ?
S7A C76A 1.785(11) . ?
S7A C77A 1.762(8) . ?
S7B O15B 1.52(4) . ?
S7B C76B 1.64(5) . ?
S7B C77B 1.78(3) . ?
O8 C47 1.209(5) . ?
O9 C47 1.363(4) . ?
O9 C48 1.476(5) . ?
O11 C66 1.223(6) . ?
O12 C66 1.323(6) . ?
O12 C67 1.465(6) . ?
N6 H6 0.8800 . ?
N6 C44 1.354(5) . ?
N6 C46 1.371(5) . ?
N7 C42 1.341(4) . ?
N7 C46 1.337(5) . ?
N8 C46 1.347(5) . ?
N9 C47 1.374(5) . ?
N10 H10 0.8800 . ?
N10 C66 1.359(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.374(6) . ?
C36 C41 1.399(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.385(6) . ?
C38 H38 0.9500 . ?
C38 C39 1.388(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.373(6) . ?
C40 H40 0.9500 . ?
C40 C41 1.399(5) . ?
C41 C42 1.477(5) . ?
C42 C43 1.408(5) . ?
C43 H43 0.9500 . ?
C43 C44 1.359(6) . ?
C44 C45 1.490(6) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C48 C49 1.499(7) . ?
C48 C50 1.510(5) . ?
C48 C51 1.522(6) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C53 1.395(5) . ?
C52 C57 1.402(6) . ?
C53 H53 0.9500 . ?
C53 C54 1.382(6) . ?
C54 H54 0.9500 . ?
C54 C55 1.383(6) . ?
C55 H55 0.9500 . ?
C55 C56 1.387(6) . ?
C56 H56 0.9500 . ?
C56 C57 1.386(6) . ?
C57 C58 1.522(6) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C58 C59 1.543(5) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C59 C60 1.513(5) . ?
C60 C61 1.382(6) . ?
C60 C65 1.407(6) . ?
C61 H61 0.9500 . ?
C61 C62 1.393(7) . ?
C62 H62 0.9500 . ?
C62 C63 1.391(8) . ?
C63 H63 0.9500 . ?
C63 C64 1.374(7) . ?
C64 H64 0.9500 . ?
C64 C65 1.398(6) . ?
C67 C68 1.513(10) . ?
C67 C69 1.511(11) . ?
C67 C70 1.516(10) . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
C71A H71A 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71C 0.9800 . ?
C71B H71D 0.9800 . ?
C71B H71E 0.9800 . ?
C71B H71F 0.9800 . ?
C72A H72A 0.9800 . ?
C72A H72B 0.9800 . ?
C72A H72C 0.9800 . ?
C72B H72D 0.9800 . ?
C72B H72E 0.9800 . ?
C72B H72F 0.9800 . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 0.9800 . ?
C76A H76A 0.9800 . ?
C76A H76B 0.9800 . ?
C76A H76C 0.9800 . ?
C76B H76D 0.9800 . ?
C76B H76E 0.9800 . ?
C76B H76F 0.9800 . ?
C77A H77A 0.9800 . ?
C77A H77B 0.9800 . ?
C77A H77C 0.9800 . ?
C77B H77D 0.9800 . ?
C77B H77E 0.9800 . ?
C77B H77F 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
O1 S1 N3 115.2(2) . . ?
O1 S1 N4 117.1(2) . . ?
O1 S1 C17 108.2(2) . . ?
N3 S1 C17 106.8(2) . . ?
N4 S1 N3 99.7(2) . . ?
N4 S1 C17 109.2(2) . . ?
O4 S2 N5 109.0(2) . . ?
O4 S2 C30 106.9(2) . . ?
N5 S2 C30 93.52(19) . . ?
C12 O3 C13 123.3(4) . . ?
C31 O6 C32 120.5(4) . . ?
C11 N1 C7 118.8(4) . . ?
C9 N2 H2 119.1 . . ?
C9 N2 C11 121.7(4) . . ?
C11 N2 H2 119.1 . . ?
C11 N3 S1 118.2(3) . . ?
C12 N4 S1 118.0(3) . . ?
S2 N5 H5 121.1 . . ?
C31 N5 S2 117.8(3) . . ?
C31 N5 H5 121.1 . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(4) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C1 C2 C3 120.7(4) . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(5) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(5) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C7 119.3(4) . . ?
C5 C6 C1 118.2(4) . . ?
C5 C6 C7 122.5(4) . . ?
N1 C7 C6 115.9(4) . . ?
N1 C7 C8 122.0(4) . . ?
C8 C7 C6 122.1(4) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.3(4) . . ?
C9 C8 H8 120.9 . . ?
N2 C9 C8 118.8(4) . . ?
N2 C9 C10 116.8(4) . . ?
C8 C9 C10 124.4(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 N2 120.4(4) . . ?
N3 C11 N1 125.1(4) . . ?
N3 C11 N2 114.5(4) . . ?
O2 C12 O3 121.8(5) . . ?
O2 C12 N4 123.0(5) . . ?
O3 C12 N4 115.3(4) . . ?
O3 C13 C14 103.1(4) . . ?
O3 C13 C15 109.3(5) . . ?
O3 C13 C16 110.3(4) . . ?
C14 C13 C16 109.2(6) . . ?
C15 C13 C14 109.4(5) . . ?
C15 C13 C16 115.0(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S1 115.3(4) . . ?
C18 C17 C22 121.6(4) . . ?
C22 C17 S1 123.0(3) . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.4(5) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(5) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.1(5) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.3(5) . . ?
C22 C21 H21 119.3 . . ?
C17 C22 C21 116.9(4) . . ?
C17 C22 C23 126.9(4) . . ?
C21 C22 C23 116.2(4) . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C22 C23 C24 112.7(4) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C23 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
C25 C24 C23 111.7(4) . . ?
C25 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C26 C25 C24 120.6(5) . . ?
C30 C25 C24 123.0(4) . . ?
C30 C25 C26 116.3(5) . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.1(6) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.2(5) . . ?
C28 C27 H27 119.4 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 119.9(5) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.4 . . ?
C28 C29 C30 119.1(6) . . ?
C30 C29 H29 120.4 . . ?
C25 C30 S2 119.4(3) . . ?
C25 C30 C29 123.2(5) . . ?
C29 C30 S2 117.4(4) . . ?
O5 C31 O6 127.8(4) . . ?
O5 C31 N5 124.0(4) . . ?
O6 C31 N5 108.2(4) . . ?
O6 C32 C33 107.1(5) . . ?
O6 C32 C34 111.7(5) . . ?
O6 C32 C35 101.0(5) . . ?
C34 C32 C33 112.7(6) . . ?
C34 C32 C35 111.7(6) . . ?
C35 C32 C33 112.0(6) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O7 S3 N8 115.54(16) . . ?
O7 S3 N9 115.98(17) . . ?
O7 S3 C52 107.63(17) . . ?
N8 S3 C52 107.46(18) . . ?
N9 S3 N8 99.35(17) . . ?
N9 S3 C52 110.49(17) . . ?
O10 S4 N10 109.6(2) . . ?
O10 S4 C65 106.8(2) . . ?
N10 S4 C65 94.93(19) . . ?
O13A S5A C71A 106.4(4) . . ?
O13A S5A C72A 105.1(4) . . ?
C71A S5A C72A 98.8(4) . . ?
O13B S5B C71B 112.1(16) . . ?
O13B S5B C72B 111.1(16) . . ?
C72B S5B C71B 107.4(16) . . ?
O14 S6 C73 105.2(4) . . ?
O14 S6 C74 107.0(3) . . ?
C73 S6 C74 98.2(3) . . ?
O15A S7A C76A 106.0(5) . . ?
O15A S7A C77A 106.4(4) . . ?
C77A S7A C76A 97.5(4) . . ?
O15B S7B C76B 107(3) . . ?
O15B S7B C77B 97.1(19) . . ?
C76B S7B C77B 98(2) . . ?
C47 O9 C48 121.4(3) . . ?
C66 O12 C67 118.9(4) . . ?
C44 N6 H6 119.2 . . ?
C44 N6 C46 121.6(3) . . ?
C46 N6 H6 119.2 . . ?
C46 N7 C42 118.2(3) . . ?
C46 N8 S3 119.6(3) . . ?
C47 N9 S3 117.1(3) . . ?
S4 N10 H10 122.8 . . ?
C66 N10 S4 114.4(3) . . ?
C66 N10 H10 122.8 . . ?
C37 C36 H36 119.7 . . ?
C37 C36 C41 120.7(4) . . ?
C41 C36 H36 119.7 . . ?
C36 C37 H37 119.6 . . ?
C36 C37 C38 120.8(3) . . ?
C38 C37 H37 119.6 . . ?
C37 C38 H38 120.4 . . ?
C37 C38 C39 119.2(4) . . ?
C39 C38 H38 120.4 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.1(4) . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.3(3) . . ?
C41 C40 H40 119.4 . . ?
C36 C41 C40 117.9(3) . . ?
C36 C41 C42 122.4(3) . . ?
C40 C41 C42 119.8(3) . . ?
N7 C42 C41 115.4(3) . . ?
N7 C42 C43 121.7(3) . . ?
C43 C42 C41 122.9(3) . . ?
C42 C43 H43 120.5 . . ?
C44 C43 C42 119.1(3) . . ?
C44 C43 H43 120.5 . . ?
N6 C44 C43 118.1(4) . . ?
N6 C44 C45 116.5(4) . . ?
C43 C44 C45 125.4(4) . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N7 C46 N6 121.3(3) . . ?
N7 C46 N8 125.3(3) . . ?
N8 C46 N6 113.5(3) . . ?
O8 C47 O9 124.3(4) . . ?
O8 C47 N9 129.3(3) . . ?
O9 C47 N9 106.5(3) . . ?
O9 C48 C49 110.8(3) . . ?
O9 C48 C50 110.2(3) . . ?
O9 C48 C51 101.6(3) . . ?
C49 C48 C50 112.2(4) . . ?
C49 C48 C51 111.9(4) . . ?
C50 C48 C51 109.6(4) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 C52 S3 116.3(3) . . ?
C53 C52 C57 121.0(4) . . ?
C57 C52 S3 122.6(3) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 C52 120.5(4) . . ?
C54 C53 H53 119.8 . . ?
C53 C54 H54 120.3 . . ?
C53 C54 C55 119.4(4) . . ?
C55 C54 H54 120.3 . . ?
C54 C55 H55 120.2 . . ?
C54 C55 C56 119.5(4) . . ?
C56 C55 H55 120.2 . . ?
C55 C56 H56 118.6 . . ?
C57 C56 C55 122.8(4) . . ?
C57 C56 H56 118.6 . . ?
C52 C57 C58 123.7(3) . . ?
C56 C57 C52 116.8(4) . . ?
C56 C57 C58 119.5(4) . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C57 C58 C59 110.9(3) . . ?
H58A C58 H58B 108.0 . . ?
C59 C58 H58A 109.5 . . ?
C59 C58 H58B 109.5 . . ?
C58 C59 H59A 108.8 . . ?
C58 C59 H59B 108.8 . . ?
H59A C59 H59B 107.7 . . ?
C60 C59 C58 113.8(3) . . ?
C60 C59 H59A 108.8 . . ?
C60 C59 H59B 108.8 . . ?
C61 C60 C59 118.8(4) . . ?
C61 C60 C65 117.8(4) . . ?
C65 C60 C59 123.4(4) . . ?
C60 C61 H61 119.5 . . ?
C60 C61 C62 121.1(5) . . ?
C62 C61 H61 119.5 . . ?
C61 C62 H62 119.9 . . ?
C63 C62 C61 120.2(5) . . ?
C63 C62 H62 119.9 . . ?
C62 C63 H63 120.0 . . ?
C64 C63 C62 120.1(4) . . ?
C64 C63 H63 120.0 . . ?
C63 C64 H64 120.3 . . ?
C63 C64 C65 119.4(5) . . ?
C65 C64 H64 120.3 . . ?
C60 C65 S4 120.9(3) . . ?
C64 C65 S4 117.5(4) . . ?
C64 C65 C60 121.4(4) . . ?
O11 C66 O12 126.0(5) . . ?
O11 C66 N10 123.4(4) . . ?
O12 C66 N10 110.6(4) . . ?
O12 C67 C68 110.8(5) . . ?
O12 C67 C69 107.9(6) . . ?
O12 C67 C70 102.0(5) . . ?
C68 C67 C70 110.4(7) . . ?
C69 C67 C68 114.2(6) . . ?
C69 C67 C70 110.9(7) . . ?
C67 C68 H68A 109.5 . . ?
C67 C68 H68B 109.5 . . ?
C67 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C67 C69 H69A 109.5 . . ?
C67 C69 H69B 109.5 . . ?
C67 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C67 C70 H70A 109.5 . . ?
C67 C70 H70B 109.5 . . ?
C67 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
S5A C71A H71A 109.5 . . ?
S5A C71A H71B 109.5 . . ?
S5A C71A H71C 109.5 . . ?
H71A C71A H71B 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
S5B C71B H71D 109.5 . . ?
S5B C71B H71E 109.5 . . ?
S5B C71B H71F 109.5 . . ?
H71D C71B H71E 109.5 . . ?
H71D C71B H71F 109.5 . . ?
H71E C71B H71F 109.5 . . ?
S5A C72A H72A 109.5 . . ?
S5A C72A H72B 109.5 . . ?
S5A C72A H72C 109.5 . . ?
H72A C72A H72B 109.5 . . ?
H72A C72A H72C 109.5 . . ?
H72B C72A H72C 109.5 . . ?
S5B C72B H72D 109.5 . . ?
S5B C72B H72E 109.5 . . ?
S5B C72B H72F 109.5 . . ?
H72D C72B H72E 109.5 . . ?
H72D C72B H72F 109.5 . . ?
H72E C72B H72F 109.5 . . ?
S6 C73 H73A 109.5 . . ?
S6 C73 H73B 109.5 . . ?
S6 C73 H73C 109.5 . . ?
H73A C73 H73B 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
S6 C74 H74A 109.5 . . ?
S6 C74 H74B 109.5 . . ?
S6 C74 H74C 109.5 . . ?
H74A C74 H74B 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
S7A C76A H76A 109.5 . . ?
S7A C76A H76B 109.5 . . ?
S7A C76A H76C 109.5 . . ?
H76A C76A H76B 109.5 . . ?
H76A C76A H76C 109.5 . . ?
H76B C76A H76C 109.5 . . ?
S7B C76B H76D 109.5 . . ?
S7B C76B H76E 109.5 . . ?
S7B C76B H76F 109.5 . . ?
H76D C76B H76E 109.5 . . ?
H76D C76B H76F 109.5 . . ?
H76E C76B H76F 109.5 . . ?
S7A C77A H77A 109.5 . . ?
S7A C77A H77B 109.5 . . ?
S7A C77A H77C 109.5 . . ?
H77A C77A H77B 109.5 . . ?
H77A C77A H77C 109.5 . . ?
H77B C77A H77C 109.5 . . ?
S7B C77B H77D 109.5 . . ?
S7B C77B H77E 109.5 . . ?
S7B C77B H77F 109.5 . . ?
H77D C77B H77E 109.5 . . ?
H77D C77B H77F 109.5 . . ?
H77E C77B H77F 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 N3 C11 N1 -4.1(6) . . . . ?
S1 N3 C11 N2 176.2(3) . . . . ?
S1 N4 C12 O2 -178.3(4) . . . . ?
S1 N4 C12 O3 3.3(6) . . . . ?
S1 C17 C18 C19 179.1(4) . . . . ?
S1 C17 C22 C21 -178.4(4) . . . . ?
S1 C17 C22 C23 2.4(7) . . . . ?
S2 N5 C31 O5 -13.0(7) . . . . ?
S2 N5 C31 O6 167.8(3) . . . . ?
O1 S1 N3 C11 -48.6(4) . . . . ?
O1 S1 N4 C12 61.9(4) . . . . ?
O1 S1 C17 C18 7.4(4) . . . . ?
O1 S1 C17 C22 -173.7(4) . . . . ?
O4 S2 N5 C31 -82.8(4) . . . . ?
O4 S2 C30 C25 157.1(4) . . . . ?
O4 S2 C30 C29 -22.4(4) . . . . ?
N1 C7 C8 C9 -0.1(6) . . . . ?
N3 S1 N4 C12 -173.2(4) . . . . ?
N3 S1 C17 C18 -117.1(4) . . . . ?
N3 S1 C17 C22 61.7(4) . . . . ?
N4 S1 N3 C11 -174.9(3) . . . . ?
N4 S1 C17 C18 135.9(4) . . . . ?
N4 S1 C17 C22 -45.2(4) . . . . ?
N5 S2 C30 C25 -91.9(4) . . . . ?
N5 S2 C30 C29 88.7(4) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C1 C6 C7 N1 10.2(5) . . . . ?
C1 C6 C7 C8 -170.1(4) . . . . ?
C2 C1 C6 C5 0.8(6) . . . . ?
C2 C1 C6 C7 -178.7(4) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C4 C5 C6 C7 178.9(4) . . . . ?
C5 C6 C7 N1 -169.2(4) . . . . ?
C5 C6 C7 C8 10.5(6) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
C6 C7 C8 C9 -179.9(4) . . . . ?
C7 N1 C11 N2 -0.3(6) . . . . ?
C7 N1 C11 N3 179.9(4) . . . . ?
C7 C8 C9 N2 -1.0(6) . . . . ?
C7 C8 C9 C10 178.1(4) . . . . ?
C9 N2 C11 N1 -0.8(6) . . . . ?
C9 N2 C11 N3 178.9(4) . . . . ?
C11 N1 C7 C6 -179.4(3) . . . . ?
C11 N1 C7 C8 0.8(6) . . . . ?
C11 N2 C9 C8 1.5(6) . . . . ?
C11 N2 C9 C10 -177.6(4) . . . . ?
C12 O3 C13 C14 -174.9(5) . . . . ?
C12 O3 C13 C15 68.8(6) . . . . ?
C12 O3 C13 C16 -58.4(7) . . . . ?
C13 O3 C12 O2 -6.0(7) . . . . ?
C13 O3 C12 N4 172.4(4) . . . . ?
C17 S1 N3 C11 71.5(4) . . . . ?
C17 S1 N4 C12 -61.5(4) . . . . ?
C17 C18 C19 C20 -1.1(8) . . . . ?
C17 C22 C23 C24 107.0(5) . . . . ?
C18 C17 C22 C21 0.4(7) . . . . ?
C18 C17 C22 C23 -178.8(4) . . . . ?
C18 C19 C20 C21 1.3(8) . . . . ?
C19 C20 C21 C22 -0.7(8) . . . . ?
C20 C21 C22 C17 -0.2(7) . . . . ?
C20 C21 C22 C23 179.1(5) . . . . ?
C21 C22 C23 C24 -72.2(5) . . . . ?
C22 C17 C18 C19 0.2(7) . . . . ?
C22 C23 C24 C25 168.8(4) . . . . ?
C23 C24 C25 C26 95.2(5) . . . . ?
C23 C24 C25 C30 -82.6(5) . . . . ?
C24 C25 C26 C27 -178.2(4) . . . . ?
C24 C25 C30 S2 -2.5(6) . . . . ?
C24 C25 C30 C29 176.9(4) . . . . ?
C25 C26 C27 C28 0.3(8) . . . . ?
C26 C25 C30 S2 179.6(3) . . . . ?
C26 C25 C30 C29 -0.9(7) . . . . ?
C26 C27 C28 C29 0.9(8) . . . . ?
C27 C28 C29 C30 -2.1(8) . . . . ?
C28 C29 C30 S2 -178.4(4) . . . . ?
C28 C29 C30 C25 2.1(7) . . . . ?
C30 S2 N5 C31 168.0(4) . . . . ?
C30 C25 C26 C27 -0.3(7) . . . . ?
C31 O6 C32 C33 -64.8(6) . . . . ?
C31 O6 C32 C34 59.0(7) . . . . ?
C31 O6 C32 C35 177.9(5) . . . . ?
C32 O6 C31 O5 1.1(7) . . . . ?
C32 O6 C31 N5 -179.6(4) . . . . ?
S3 N8 C46 N6 -176.4(3) . . . . ?
S3 N8 C46 N7 3.3(5) . . . . ?
S3 N9 C47 O8 -7.7(6) . . . . ?
S3 N9 C47 O9 172.5(2) . . . . ?
S3 C52 C53 C54 -176.4(3) . . . . ?
S3 C52 C57 C56 175.7(3) . . . . ?
S3 C52 C57 C58 -6.0(5) . . . . ?
S4 N10 C66 O11 0.0(7) . . . . ?
S4 N10 C66 O12 179.5(4) . . . . ?
O7 S3 N8 C46 56.2(3) . . . . ?
O7 S3 N9 C47 -55.8(3) . . . . ?
O7 S3 C52 C53 -0.8(3) . . . . ?
O7 S3 C52 C57 -178.1(3) . . . . ?
O10 S4 N10 C66 82.1(4) . . . . ?
O10 S4 C65 C60 -156.6(3) . . . . ?
O10 S4 C65 C64 19.9(4) . . . . ?
N7 C42 C43 C44 -1.3(5) . . . . ?
N8 S3 N9 C47 179.7(3) . . . . ?
N8 S3 C52 C53 124.3(3) . . . . ?
N8 S3 C52 C57 -53.1(3) . . . . ?
N9 S3 N8 C46 -179.0(3) . . . . ?
N9 S3 C52 C53 -128.3(3) . . . . ?
N9 S3 C52 C57 54.3(3) . . . . ?
N10 S4 C65 C60 91.3(3) . . . . ?
N10 S4 C65 C64 -92.2(4) . . . . ?
C36 C37 C38 C39 0.1(6) . . . . ?
C36 C41 C42 N7 -174.0(3) . . . . ?
C36 C41 C42 C43 6.7(5) . . . . ?
C37 C36 C41 C40 -0.6(6) . . . . ?
C37 C36 C41 C42 -179.7(4) . . . . ?
C37 C38 C39 C40 -1.4(6) . . . . ?
C38 C39 C40 C41 1.7(6) . . . . ?
C39 C40 C41 C36 -0.7(6) . . . . ?
C39 C40 C41 C42 178.3(4) . . . . ?
C40 C41 C42 N7 6.9(5) . . . . ?
C40 C41 C42 C43 -172.4(4) . . . . ?
C41 C36 C37 C38 1.0(6) . . . . ?
C41 C42 C43 C44 177.9(3) . . . . ?
C42 N7 C46 N6 0.9(5) . . . . ?
C42 N7 C46 N8 -178.7(3) . . . . ?
C42 C43 C44 N6 0.4(5) . . . . ?
C42 C43 C44 C45 -178.4(4) . . . . ?
C44 N6 C46 N7 -1.9(5) . . . . ?
C44 N6 C46 N8 177.8(3) . . . . ?
C46 N6 C44 C43 1.2(5) . . . . ?
C46 N6 C44 C45 -180.0(3) . . . . ?
C46 N7 C42 C41 -178.7(3) . . . . ?
C46 N7 C42 C43 0.6(5) . . . . ?
C47 O9 C48 C49 67.2(5) . . . . ?
C47 O9 C48 C50 -57.6(5) . . . . ?
C47 O9 C48 C51 -173.7(4) . . . . ?
C48 O9 C47 O8 -7.2(6) . . . . ?
C48 O9 C47 N9 172.5(3) . . . . ?
C52 S3 N8 C46 -63.9(3) . . . . ?
C52 S3 N9 C47 67.0(3) . . . . ?
C52 C53 C54 C55 0.4(5) . . . . ?
C52 C57 C58 C59 -102.5(4) . . . . ?
C53 C52 C57 C56 -1.5(5) . . . . ?
C53 C52 C57 C58 176.7(3) . . . . ?
C53 C54 C55 C56 -1.2(5) . . . . ?
C54 C55 C56 C57 0.6(6) . . . . ?
C55 C56 C57 C52 0.7(5) . . . . ?
C55 C56 C57 C58 -177.6(3) . . . . ?
C56 C57 C58 C59 75.7(4) . . . . ?
C57 C52 C53 C54 1.0(5) . . . . ?
C57 C58 C59 C60 171.2(3) . . . . ?
C58 C59 C60 C61 -90.7(5) . . . . ?
C58 C59 C60 C65 90.6(5) . . . . ?
C59 C60 C61 C62 -176.6(4) . . . . ?
C59 C60 C65 S4 -7.7(5) . . . . ?
C59 C60 C65 C64 176.0(4) . . . . ?
C60 C61 C62 C63 0.5(7) . . . . ?
C61 C60 C65 S4 173.7(3) . . . . ?
C61 C60 C65 C64 -2.7(6) . . . . ?
C61 C62 C63 C64 -2.6(7) . . . . ?
C62 C63 C64 C65 2.0(7) . . . . ?
C63 C64 C65 S4 -175.8(4) . . . . ?
C63 C64 C65 C60 0.7(6) . . . . ?
C65 S4 N10 C66 -168.2(4) . . . . ?
C65 C60 C61 C62 2.1(6) . . . . ?
C66 O12 C67 C68 66.0(7) . . . . ?
C66 O12 C67 C69 -59.7(7) . . . . ?
C66 O12 C67 C70 -176.6(7) . . . . ?
C67 O12 C66 O11 -9.2(9) . . . . ?
C67 O12 C66 N10 171.3(5) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_285
_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 2.029
_oxdiff_exptl_absorpt_empirical_full_min 0.452
####################################################################### 
# 
# 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_az14355398
_database_code_depnum_ccdc_archive 'CCDC 2517069'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-12-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Cl N5 O2 S, 2(C2 H6 O S)'
_chemical_formula_sum            'C23 H24 Cl N5 O4 S3'
_chemical_formula_weight         566.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S Cl'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.4189(2)
_cell_length_b                   15.0573(3)
_cell_length_c                   19.8047(2)
_cell_angle_alpha                85.3950(10)
_cell_angle_beta                 82.9180(10)
_cell_angle_gamma                66.468(2)
_cell_volume                     3909.85(12)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    66685
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.8490
_cell_measurement_theta_min      3.3540
_shelx_estimated_absorpt_T_max   0.668
_shelx_estimated_absorpt_T_min   0.461
_exptl_absorpt_coefficient_mu    3.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1764
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -5 4 0.0367
0 0 -1 0.0688
2 5 -5 0.1398
-5 0 -2 0.0624
4 -5 1 0.0165
5 4 2 0.0995
-3 5 -1 0.1387
2 5 5 0.1159
0 -1 1 0.0385
4 -1 -5 0.0299
5 2 -5 0.0681
-5 -3 2 0.0562
-5 3 3 0.0861
3 -5 5 0.0350
5 0 -2 0.0423
5 2 -1 0.0693
-2 -3 -5 0.1000

_exptl_crystal_preparation       
'The material was recrystallized from DMSO by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow evaporation'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.113
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0016 -4.9983 3.9963 0.1925 -0.3226 0.4971
0.0002 -0.0000 -0.9991 -0.0223 0.0751 0.0013
2.0018 4.9982 -4.9954 -0.2148 0.3977 -0.4959
-4.9908 0.0057 -1.9976 0.5220 0.2593 -0.0925
3.9883 -5.0052 0.9982 -0.5545 -0.2282 0.6151
4.9944 3.9949 1.9979 -0.4232 -0.2066 -0.3398
-2.9900 5.0041 -0.9983 0.4411 0.2064 -0.5961
2.0002 4.9985 4.9957 0.0085 -0.3533 -0.5087
-0.0011 -1.0001 0.9990 -0.0024 -0.0883 0.1068
3.9928 -1.0049 -4.9962 -0.5897 0.2751 0.1906
4.9937 1.9944 -4.9960 -0.6289 0.2928 -0.1146
-4.9942 -2.9946 1.9986 0.5372 -0.0806 0.2265
-4.9889 3.0062 2.9982 0.7077 -0.0767 -0.4231
2.9894 -5.0040 4.9948 -0.3518 -0.5068 0.5909
4.9915 -0.0058 -1.9989 -0.6113 0.0411 0.0977
4.9931 1.9945 -0.9996 -0.5396 -0.0076 -0.1198
-1.9984 -2.9983 -4.9956 0.0409 0.3796 0.2926

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            102474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.830
_diffrn_reflns_theta_min         3.203
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00 114.00   0.50    0.30    --   50.70-137.00  75.00  146
  2  ω     38.00 111.00   0.50    0.30    --   50.70-132.00-107.00  146
  3  ω   -124.00 -66.00   0.50    0.30    --  -51.20-137.00  75.00  116
  4  ω   -125.00 -69.00   0.50    0.30    --  -51.20-132.00-107.00  112
  5  ω    -91.00 -17.00   0.50    0.30    --  -51.20 132.00 -39.00  148
  6  ω    -95.00 -19.00   0.50    0.30    --  -51.20 137.00 137.00  152
  7  ω    -95.00 -19.00   0.50    0.71    --  -79.95 137.00 137.00  152
  8  ω   -154.00 -69.00   0.50    0.71    --  -79.95-132.00-107.00  170
  9  ω   -153.00 -66.00   0.50    0.71    --  -79.95-137.00  75.00  174
 10  ω     91.00 170.00   0.50    0.71    --   96.59 132.00 -39.00  158
 11  ω     41.00 121.00   0.50    0.71    --   96.59-137.00  75.00  160
 12  ω     87.00 170.00   0.50    0.71    --   96.59 137.00 137.00  166
 13  ω     38.00 117.00   0.50    0.71    --   96.59-132.00-107.00  158
 14  ω     41.00 120.00   0.50    0.71    --  108.39-137.00  75.00  158
 15  ω     87.00 178.00   0.50    0.71    --  108.39 137.00 137.00  182
 16  ω     38.00 117.00   0.50    0.71    --  108.39-132.00-107.00  158
 17  ω     91.00 178.00   0.50    0.71    --  108.39 132.00 -39.00  174
 18  ω     -1.00  25.00   0.50    0.30    --   36.00  94.00-103.74   52
 19  ω      1.00  28.00   0.50    0.30    --   36.00  91.00  42.31   54
 20  ω     17.00  43.00   0.50    0.30    --   44.00  78.00   3.33   52
 21  ω     80.00 119.00   0.50    0.30    --   50.70  77.00 -90.00   78
 22  ω   -120.00 -80.00   0.50    0.30    --  -51.20 -77.00  30.00   80
 23  ω   -131.00 -37.00   0.50    0.30    --  -60.00 -70.00 101.11  188
 24  ω   -145.00 -50.00   0.50    0.71    --  -72.00 -65.00  73.31  190
 25  ω   -148.00 -80.00   0.50    0.71    --  -79.95 -77.00-180.00  136
 26  ω   -159.00 -68.00   0.50    0.71    --  -88.50 -72.00 -12.44  182
 27  ω   -159.00 -68.00   0.50    0.71    --  -88.50 -72.00 -45.34  182
 28  ω     28.00 105.00   0.50    0.71    --   96.59 -95.00 -60.00  154
 29  ω     95.00 171.00   0.50    0.71    --   96.59 125.00 -60.00  152
 30  ω     95.00 171.00   0.50    0.71    --   96.59 125.00 120.00  152
 31  ω     95.00 171.00   0.50    0.71    --   96.59 125.00  30.00  152
 32  ω     34.00 112.00   0.50    0.71    --   96.59-125.00 150.00  156
 33  ω     80.00 165.00   0.50    0.71    --   96.59  77.00-150.00  170
 34  ω     40.00 105.00   0.50    0.71    --  108.39 -95.00 -90.00  130
 35  ω     31.00 125.00   0.50    0.71    --  108.39 -45.00  30.00  188
 36  ω     40.00 105.00   0.50    0.71    --  108.39 -95.00  90.00  130
 37  ω     82.00 177.00   0.50    0.71    --  108.39  77.00  30.00  190
 38  ω    -36.00  -7.00   0.50    0.30    --   16.00 117.00 165.06   58
 39  ω     12.00  41.00   0.50    0.30    --   40.00  80.00 -72.63   58
 40  ω     17.00  43.00   0.50    0.30    --   44.00  78.00 165.34   52
 41  ω     16.00  43.00   0.50    0.30    --   44.00  79.00 -46.21   54
 42  ω     17.00  43.00   0.50    0.30    --   44.00  78.00-149.18   52
 43  ω     17.00  43.00   0.50    0.30    --   44.00  78.00  71.41   52
 44  ω     36.00 131.00   0.50    0.30    --   60.00  72.00  21.93  190
 45  ω     40.00 135.00   0.50    0.30    --   64.00  72.00-147.45  190
 46  ω   -151.00 -77.00   0.50    0.71    --  -80.00 -71.00  42.24  148
 47  ω   -155.00 -61.00   0.50    0.71    --  -84.00 -70.00-102.41  188
 48  ω   -160.00 -66.00   0.50    0.71    --  -88.50 -69.00 157.77  188
 49  ω     80.00 165.00   0.50    0.71    --   96.59  77.00  90.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1134970000
_diffrn_orient_matrix_UB_12      0.0247956000
_diffrn_orient_matrix_UB_13      0.0223351000
_diffrn_orient_matrix_UB_21      -0.0218460000
_diffrn_orient_matrix_UB_22      0.0131895000
_diffrn_orient_matrix_UB_23      -0.0751729000
_diffrn_orient_matrix_UB_31      0.0189259000
_diffrn_orient_matrix_UB_32      -0.1080690000
_diffrn_orient_matrix_UB_33      -0.0012833000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                14630
_reflns_number_total             15917
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.810
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1000
_refine_ls_number_reflns         15917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+4.2397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1100
_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:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C17(H17), C20(H20),
  C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C34(H34), C36(H36),
 C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46), C53(H53), C55(H55)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C29(H29A,H29B,H29C), C48(H48A,H48B,H48C), C58(H58A,H58B,
 H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C62(H62A,
 H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C),
 C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C69(H69A,H69B,
 H69C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17021(4) 0.37421(4) 0.71401(3) 0.03205(12) Uani 1 1 d . . . . .
S1 S 0.25593(3) 0.00247(3) 0.82506(2) 0.01940(10) Uani 1 1 d . . . . .
O1 O 0.01886(11) -0.00274(11) 0.78706(8) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.35524(11) -0.04147(10) 0.78850(7) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.09418(12) 0.08065(11) 0.93815(8) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.21977(13) 0.01662(12) 1.01420(9) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.287(2) -0.017(2) 1.0175(14) 0.033(7) Uiso 1 1 d . . . . .
N3 N 0.27199(12) 0.00881(12) 0.90106(8) 0.0209(3) Uani 1 1 d . . . . .
N4 N 0.18067(13) -0.04813(12) 0.81771(9) 0.0228(3) Uani 1 1 d . . . . .
N5 N -0.13922(15) 0.19082(16) 0.70304(11) 0.0374(5) Uani 1 1 d . . . . .
C1 C -0.10620(16) 0.19123(16) 0.91133(11) 0.0269(4) Uani 1 1 d . . . . .
H1 H -0.052354 0.182082 0.876206 0.032 Uiso 1 1 calc R U . . .
C2 C -0.20620(17) 0.23869(17) 0.89636(12) 0.0310(5) Uani 1 1 d . . . . .
H2A H -0.220574 0.262447 0.851301 0.037 Uiso 1 1 calc R U . . .
C3 C -0.28531(16) 0.25139(16) 0.94746(12) 0.0299(5) Uani 1 1 d . . . . .
H3 H -0.353878 0.283391 0.937361 0.036 Uiso 1 1 calc R U . . .
C4 C -0.26372(16) 0.21724(16) 1.01305(12) 0.0278(4) Uani 1 1 d . . . . .
H4 H -0.317785 0.225540 1.047871 0.033 Uiso 1 1 calc R U . . .
C5 C -0.16325(16) 0.17068(14) 1.02856(11) 0.0233(4) Uani 1 1 d . . . . .
H5 H -0.149122 0.148552 1.073919 0.028 Uiso 1 1 calc R U . . .
C6 C -0.08389(15) 0.15676(14) 0.97749(10) 0.0202(4) Uani 1 1 d . . . . .
C7 C 0.02340(14) 0.10569(13) 0.99247(10) 0.0190(4) Uani 1 1 d . . . . .
C8 C 0.04957(15) 0.08551(14) 1.05917(10) 0.0214(4) Uani 1 1 d . . . . .
H8 H -0.001346 0.102912 1.096673 0.026 Uiso 1 1 calc R U . . .
C9 C 0.15083(15) 0.03982(14) 1.06940(10) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.19042(16) 0.01536(16) 1.13721(10) 0.0261(4) Uani 1 1 d . . . . .
H10A H 0.190211 0.073686 1.156028 0.039 Uiso 1 1 calc R U . . .
H10B H 0.260026 -0.033955 1.132452 0.039 Uiso 1 1 calc R U . . .
H10C H 0.147131 -0.009793 1.167887 0.039 Uiso 1 1 calc R U . . .
C11 C 0.19135(14) 0.03671(14) 0.94970(10) 0.0189(4) Uani 1 1 d . . . . .
C12 C 0.09300(15) 0.01529(15) 0.79228(10) 0.0225(4) Uani 1 1 d . . . . .
C13 C 0.09778(15) 0.11195(15) 0.77067(10) 0.0211(4) Uani 1 1 d . . . . .
C14 C 0.18580(15) 0.11713(14) 0.78678(10) 0.0199(4) Uani 1 1 d . . . . .
C15 C 0.21185(15) 0.19603(14) 0.77167(10) 0.0212(4) Uani 1 1 d . . . . .
H15 H 0.273224 0.197148 0.783537 0.025 Uiso 1 1 calc R U . . .
C16 C 0.14130(16) 0.27402(15) 0.73765(10) 0.0235(4) Uani 1 1 d . . . . .
C17 C 0.05114(16) 0.27318(15) 0.72037(10) 0.0244(4) Uani 1 1 d . . . . .
H17 H 0.005256 0.327651 0.697179 0.029 Uiso 1 1 calc R U . . .
C18 C 0.02826(15) 0.19137(15) 0.73738(10) 0.0228(4) Uani 1 1 d . . . . .
C19 C -0.06444(16) 0.18907(16) 0.71843(11) 0.0273(4) Uani 1 1 d . . . . .
Cl2 Cl 0.55297(4) -0.03227(4) 0.59590(3) 0.03672(13) Uani 1 1 d . . . . .
S2 S 0.31270(4) 0.34327(3) 0.51407(2) 0.02039(10) Uani 1 1 d . . . . .
O3 O 0.07561(11) 0.31203(11) 0.55813(8) 0.0273(3) Uani 1 1 d . . . . .
O4 O 0.34971(13) 0.39740(11) 0.55215(7) 0.0298(3) Uani 1 1 d . . . . .
N6 N 0.27566(12) 0.25662(11) 0.39574(8) 0.0175(3) Uani 1 1 d . . . . .
N7 N 0.38809(12) 0.31240(12) 0.32685(8) 0.0191(3) Uani 1 1 d . . . . .
H7 H 0.429(2) 0.345(2) 0.3260(14) 0.037(7) Uiso 1 1 d . . . . .
N8 N 0.36338(13) 0.34180(12) 0.43896(8) 0.0211(3) Uani 1 1 d . . . . .
N9 N 0.19326(13) 0.37808(12) 0.52151(9) 0.0232(3) Uani 1 1 d . . . . .
N10 N 0.10178(15) 0.07112(15) 0.59806(10) 0.0323(4) Uani 1 1 d . . . . .
C20 C 0.14374(16) 0.16186(15) 0.41518(10) 0.0228(4) Uani 1 1 d . . . . .
H20 H 0.166193 0.179109 0.453340 0.027 Uiso 1 1 calc R U . . .
C21 C 0.07132(16) 0.12173(15) 0.42526(11) 0.0238(4) Uani 1 1 d . . . . .
H21 H 0.044338 0.112109 0.470175 0.029 Uiso 1 1 calc R U . . .
C22 C 0.03826(16) 0.09569(15) 0.37028(11) 0.0245(4) Uani 1 1 d . . . . .
H22 H -0.010239 0.067004 0.377327 0.029 Uiso 1 1 calc R U . . .
C23 C 0.07634(17) 0.11173(17) 0.30489(11) 0.0276(4) Uani 1 1 d . . . . .
H23 H 0.052743 0.095254 0.266947 0.033 Uiso 1 1 calc R U . . .
C24 C 0.14882(16) 0.15176(15) 0.29445(10) 0.0234(4) Uani 1 1 d . . . . .
H24 H 0.174794 0.161995 0.249373 0.028 Uiso 1 1 calc R U . . .
C25 C 0.18393(14) 0.17713(13) 0.34958(10) 0.0180(4) Uani 1 1 d . . . . .
C26 C 0.25865(14) 0.22301(13) 0.33945(10) 0.0173(4) Uani 1 1 d . . . . .
C27 C 0.30804(15) 0.23178(14) 0.27504(10) 0.0204(4) Uani 1 1 d . . . . .
H27 H 0.295865 0.206814 0.236005 0.024 Uiso 1 1 calc R U . . .
C28 C 0.37453(15) 0.27750(14) 0.27000(10) 0.0203(4) Uani 1 1 d . . . . .
C29 C 0.43481(17) 0.29041(17) 0.20550(11) 0.0270(4) Uani 1 1 d . . . . .
H29A H 0.497894 0.232535 0.198767 0.041 Uiso 1 1 calc R U . . .
H29B H 0.451152 0.347096 0.208609 0.041 Uiso 1 1 calc R U . . .
H29C H 0.394802 0.300045 0.166964 0.041 Uiso 1 1 calc R U . . .
C30 C 0.33944(14) 0.30211(13) 0.38857(10) 0.0180(4) Uani 1 1 d . . . . .
C31 C 0.16348(15) 0.30494(14) 0.54699(10) 0.0206(4) Uani 1 1 d . . . . .
C32 C 0.25303(15) 0.21212(14) 0.56133(9) 0.0199(4) Uani 1 1 d . . . . .
C33 C 0.34386(15) 0.22337(14) 0.54777(9) 0.0194(4) Uani 1 1 d . . . . .
C34 C 0.43839(16) 0.15147(15) 0.55663(10) 0.0233(4) Uani 1 1 d . . . . .
H34 H 0.499355 0.162035 0.546131 0.028 Uiso 1 1 calc R U . . .
C35 C 0.43831(17) 0.06258(16) 0.58196(11) 0.0264(4) Uani 1 1 d . . . . .
C36 C 0.35000(17) 0.04563(15) 0.59398(11) 0.0256(4) Uani 1 1 d . . . . .
H36 H 0.353238 -0.016805 0.609510 0.031 Uiso 1 1 calc R U . . .
C37 C 0.25581(16) 0.12034(15) 0.58331(10) 0.0212(4) Uani 1 1 d . . . . .
C38 C 0.16731(17) 0.09696(15) 0.59193(10) 0.0252(4) Uani 1 1 d . . . . .
Cl3 Cl 1.12879(5) 0.27982(4) 0.94809(3) 0.03476(13) Uani 1 1 d . . . . .
S3 S 1.01653(4) 0.66178(3) 0.85297(2) 0.02037(10) Uani 1 1 d . . . . .
O5 O 0.74605(11) 0.71833(12) 0.88931(8) 0.0330(4) Uani 1 1 d . . . . .
O6 O 1.07623(12) 0.68660(11) 0.89522(7) 0.0273(3) Uani 1 1 d . . . . .
N11 N 0.96135(12) 0.58997(11) 0.73485(8) 0.0187(3) Uani 1 1 d . . . . .
N12 N 1.07790(13) 0.63876(12) 0.66466(8) 0.0193(3) Uani 1 1 d . . . . .
H12 H 1.125(2) 0.665(2) 0.6630(15) 0.041(8) Uiso 1 1 d . . . . .
N13 N 1.06939(13) 0.65264(13) 0.77862(8) 0.0228(3) Uani 1 1 d . . . . .
N14 N 0.89931(14) 0.73110(13) 0.85772(9) 0.0260(4) Uani 1 1 d . . . . .
N15 N 0.67563(17) 0.5392(2) 0.95639(12) 0.0496(6) Uani 1 1 d . . . . .
C39 C 0.83724(16) 0.47945(15) 0.63556(10) 0.0230(4) Uani 1 1 d . . . . .
H39 H 0.868270 0.483087 0.590815 0.028 Uiso 1 1 calc R U . . .
C40 C 0.76783(17) 0.43616(16) 0.64719(11) 0.0262(4) Uani 1 1 d . . . . .
H40 H 0.751701 0.410128 0.610286 0.031 Uiso 1 1 calc R U . . .
C41 C 0.72162(16) 0.43044(15) 0.71223(11) 0.0250(4) Uani 1 1 d . . . . .
H41 H 0.673870 0.400912 0.719824 0.030 Uiso 1 1 calc R U . . .
C42 C 0.74554(17) 0.46798(16) 0.76584(11) 0.0266(4) Uani 1 1 d . . . . .
H42 H 0.714326 0.464025 0.810483 0.032 Uiso 1 1 calc R U . . .
C43 C 0.81511(16) 0.51151(16) 0.75472(11) 0.0254(4) Uani 1 1 d . . . . .
H43 H 0.831076 0.537226 0.791857 0.030 Uiso 1 1 calc R U . . .
C44 C 0.86170(14) 0.51776(13) 0.68944(10) 0.0183(4) Uani 1 1 d . . . . .
C45 C 0.93694(14) 0.56287(13) 0.67836(10) 0.0181(4) Uani 1 1 d . . . . .
C46 C 0.98155(15) 0.57507(14) 0.61336(10) 0.0197(4) Uani 1 1 d . . . . .
H46 H 0.962358 0.556865 0.574151 0.024 Uiso 1 1 calc R U . . .
C47 C 1.05397(14) 0.61410(13) 0.60751(10) 0.0184(4) Uani 1 1 d . . . . .
C48 C 1.11003(15) 0.62894(15) 0.54180(10) 0.0221(4) Uani 1 1 d . . . . .
H48A H 1.064119 0.648808 0.505787 0.033 Uiso 1 1 calc R U . . .
H48B H 1.167581 0.568257 0.529838 0.033 Uiso 1 1 calc R U . . .
H48C H 1.135151 0.679490 0.546688 0.033 Uiso 1 1 calc R U . . .
C49 C 1.03215(15) 0.62678(14) 0.72719(10) 0.0195(4) Uani 1 1 d . . . . .
C50 C 0.83947(16) 0.68283(15) 0.88259(10) 0.0245(4) Uani 1 1 d . . . . .
C51 C 0.89979(15) 0.57824(15) 0.90161(9) 0.0205(4) Uani 1 1 d . . . . .
C52 C 1.00258(14) 0.55400(14) 0.88619(9) 0.0189(4) Uani 1 1 d . . . . .
C53 C 1.07579(15) 0.46304(15) 0.89808(10) 0.0217(4) Uani 1 1 d . . . . .
H53 H 1.146103 0.448138 0.886018 0.026 Uiso 1 1 calc R U . . .
C54 C 1.04064(16) 0.39416(15) 0.92884(10) 0.0239(4) Uani 1 1 d . . . . .
C55 C 0.93768(17) 0.41449(16) 0.94506(10) 0.0253(4) Uani 1 1 d . . . . .
H55 H 0.916089 0.365870 0.965693 0.030 Uiso 1 1 calc R U . . .
C56 C 0.86639(16) 0.50741(16) 0.93060(10) 0.0235(4) Uani 1 1 d . . . . .
C57 C 0.75955(18) 0.5274(2) 0.94483(11) 0.0340(5) Uani 1 1 d . . . . .
S4 S 0.72211(4) 0.12751(4) 0.56242(3) 0.02793(12) Uani 1 1 d . . . . .
O7 O 0.66504(13) 0.12850(14) 0.50396(9) 0.0389(4) Uani 1 1 d . . . . .
C58 C 0.66873(19) 0.24904(18) 0.59166(13) 0.0366(5) Uani 1 1 d . . . . .
H58A H 0.598102 0.265154 0.610667 0.055 Uiso 1 1 calc R U . . .
H58B H 0.670697 0.294007 0.553425 0.055 Uiso 1 1 calc R U . . .
H58C H 0.708188 0.254411 0.626876 0.055 Uiso 1 1 calc R U . . .
C59 C 0.84123(18) 0.12867(18) 0.52537(13) 0.0345(5) Uani 1 1 d . . . . .
H59A H 0.829127 0.182923 0.492088 0.052 Uiso 1 1 calc R U . . .
H59B H 0.881197 0.067613 0.502584 0.052 Uiso 1 1 calc R U . . .
H59C H 0.878621 0.136104 0.561149 0.052 Uiso 1 1 calc R U . . .
S5 S 0.51244(4) 0.17506(5) 0.74618(3) 0.03437(13) Uani 1 1 d . . . . .
O8 O 0.41782(12) 0.22724(13) 0.79212(9) 0.0385(4) Uani 1 1 d . . . . .
C60 C 0.61193(18) 0.19526(19) 0.77857(14) 0.0388(6) Uani 1 1 d . . . . .
H60A H 0.613619 0.176141 0.827035 0.058 Uiso 1 1 calc R U . . .
H60B H 0.599808 0.264142 0.772839 0.058 Uiso 1 1 calc R U . . .
H60C H 0.677130 0.156620 0.753681 0.058 Uiso 1 1 calc R U . . .
C61 C 0.5535(2) 0.0483(2) 0.77042(16) 0.0458(6) Uani 1 1 d . . . . .
H61A H 0.503697 0.024044 0.759316 0.069 Uiso 1 1 calc R U . . .
H61B H 0.559570 0.039829 0.819494 0.069 Uiso 1 1 calc R U . . .
H61C H 0.619721 0.012159 0.745651 0.069 Uiso 1 1 calc R U . . .
S6 S 0.49585(4) 0.83817(4) 0.99836(3) 0.02747(12) Uani 1 1 d . . . . .
O9 O 0.41450(11) 0.91713(11) 1.04112(8) 0.0289(3) Uani 1 1 d . . . . .
C62 C 0.52688(17) 0.89675(17) 0.92261(11) 0.0291(5) Uani 1 1 d . . . . .
H62A H 0.539994 0.952349 0.934446 0.044 Uiso 1 1 calc R U . . .
H62B H 0.470007 0.919163 0.894390 0.044 Uiso 1 1 calc R U . . .
H62C H 0.587727 0.851007 0.897269 0.044 Uiso 1 1 calc R U . . .
C63 C 0.60989(17) 0.8107(2) 1.03701(13) 0.0389(6) Uani 1 1 d . . . . .
H63A H 0.602592 0.785379 1.083638 0.058 Uiso 1 1 calc R U . . .
H63B H 0.622907 0.869621 1.037934 0.058 Uiso 1 1 calc R U . . .
H63C H 0.666865 0.761847 1.010697 0.058 Uiso 1 1 calc R U . . .
S7 S 0.20952(4) 0.79059(4) 0.70302(3) 0.02358(11) Uani 1 1 d . . . . .
O10 O 0.21457(11) 0.71473(11) 0.65455(8) 0.0265(3) Uani 1 1 d . . . . .
C64 C 0.30768(18) 0.82825(16) 0.66584(11) 0.0279(4) Uani 1 1 d . . . . .
H64A H 0.289674 0.861352 0.621767 0.042 Uiso 1 1 calc R U . . .
H64B H 0.371781 0.771408 0.659227 0.042 Uiso 1 1 calc R U . . .
H64C H 0.315495 0.872661 0.696104 0.042 Uiso 1 1 calc R U . . .
C65 C 0.26952(16) 0.72441(15) 0.77529(11) 0.0252(4) Uani 1 1 d . . . . .
H65A H 0.335999 0.674736 0.760202 0.038 Uiso 1 1 calc R U . . .
H65B H 0.226957 0.693330 0.800450 0.038 Uiso 1 1 calc R U . . .
H65C H 0.278579 0.768791 0.804957 0.038 Uiso 1 1 calc R U . . .
S8 S 0.46989(4) 0.43436(4) 0.88591(3) 0.03154(12) Uani 1 1 d . . . . .
O11 O 0.53524(14) 0.42392(15) 0.82018(10) 0.0448(4) Uani 1 1 d . . . . .
C66 C 0.34643(19) 0.4512(2) 0.86543(13) 0.0383(5) Uani 1 1 d . . . . .
H66A H 0.350333 0.392975 0.844366 0.057 Uiso 1 1 calc R U . . .
H66B H 0.321812 0.506993 0.833600 0.057 Uiso 1 1 calc R U . . .
H66C H 0.299503 0.462995 0.907098 0.057 Uiso 1 1 calc R U . . .
C67 C 0.4381(2) 0.55458(19) 0.91243(13) 0.0377(5) Uani 1 1 d . . . . .
H67A H 0.411068 0.601013 0.875014 0.056 Uiso 1 1 calc R U . . .
H67B H 0.499110 0.560175 0.925060 0.056 Uiso 1 1 calc R U . . .
H67C H 0.386677 0.568471 0.951776 0.056 Uiso 1 1 calc R U . . .
S9 S 0.49182(4) 0.52103(4) 0.63616(3) 0.02570(11) Uani 1 1 d . . . . .
O12 O 0.48379(11) 0.60041(11) 0.68178(8) 0.0252(3) Uani 1 1 d . . . . .
C68 C 0.4058(2) 0.47233(18) 0.67887(12) 0.0349(5) Uani 1 1 d . . . . .
H68A H 0.338277 0.524430 0.686819 0.052 Uiso 1 1 calc R U . . .
H68B H 0.429815 0.442227 0.722584 0.052 Uiso 1 1 calc R U . . .
H68C H 0.401915 0.423492 0.650758 0.052 Uiso 1 1 calc R U . . .
C69 C 0.42289(16) 0.58154(16) 0.56572(11) 0.0255(4) Uani 1 1 d . . . . .
H69A H 0.461489 0.613177 0.536451 0.038 Uiso 1 1 calc R U . . .
H69B H 0.356803 0.630413 0.582426 0.038 Uiso 1 1 calc R U . . .
H69C H 0.412489 0.534302 0.539560 0.038 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 C16 1.735(2) . ?
S1 O2 1.4413(14) . ?
S1 N3 1.5667(17) . ?
S1 N4 1.5800(17) . ?
S1 C14 1.778(2) . ?
O1 C12 1.221(2) . ?
N1 C7 1.352(3) . ?
N1 C11 1.329(2) . ?
N2 H2 0.91(3) . ?
N2 C9 1.350(3) . ?
N2 C11 1.363(2) . ?
N3 C11 1.362(3) . ?
N4 C12 1.371(3) . ?
N5 C19 1.146(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C1 C6 1.397(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 C7 1.483(3) . ?
C7 C8 1.395(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(3) . ?
C9 C10 1.486(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.510(3) . ?
C13 C14 1.379(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(3) . ?
C16 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(3) . ?
C18 C19 1.446(3) . ?
Cl2 C35 1.736(2) . ?
S2 O4 1.4362(14) . ?
S2 N8 1.5722(17) . ?
S2 N9 1.5785(18) . ?
S2 C33 1.772(2) . ?
O3 C31 1.222(3) . ?
N6 C26 1.348(2) . ?
N6 C30 1.338(2) . ?
N7 H7 0.90(3) . ?
N7 C28 1.346(2) . ?
N7 C30 1.362(3) . ?
N8 C30 1.348(2) . ?
N9 C31 1.374(3) . ?
N10 C38 1.147(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C20 C25 1.396(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.397(3) . ?
C25 C26 1.482(3) . ?
C26 C27 1.406(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.377(3) . ?
C28 C29 1.499(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 C32 1.512(3) . ?
C32 C33 1.378(3) . ?
C32 C37 1.402(3) . ?
C33 C34 1.382(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.391(3) . ?
C35 C36 1.385(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.403(3) . ?
C37 C38 1.441(3) . ?
Cl3 C54 1.730(2) . ?
S3 O6 1.4371(15) . ?
S3 N13 1.5619(17) . ?
S3 N14 1.5884(19) . ?
S3 C52 1.779(2) . ?
O5 C50 1.229(3) . ?
N11 C45 1.352(2) . ?
N11 C49 1.331(3) . ?
N12 H12 0.91(3) . ?
N12 C47 1.343(2) . ?
N12 C49 1.363(3) . ?
N13 C49 1.358(2) . ?
N14 C50 1.361(3) . ?
N15 C57 1.147(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.386(3) . ?
C39 C44 1.396(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.388(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.381(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.390(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.396(3) . ?
C44 C45 1.481(3) . ?
C45 C46 1.399(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.378(3) . ?
C47 C48 1.495(3) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C50 C51 1.507(3) . ?
C51 C52 1.377(3) . ?
C51 C56 1.394(3) . ?
C52 C53 1.379(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.395(3) . ?
C54 C55 1.391(3) . ?
C55 H55 0.9500 . ?
C55 C56 1.399(3) . ?
C56 C57 1.442(3) . ?
S4 O7 1.4967(17) . ?
S4 C58 1.792(3) . ?
S4 C59 1.789(2) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
S5 O8 1.5030(18) . ?
S5 C60 1.780(3) . ?
S5 C61 1.801(3) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
S6 O9 1.5197(15) . ?
S6 C62 1.779(2) . ?
S6 C63 1.782(2) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
S7 O10 1.5245(15) . ?
S7 C64 1.784(2) . ?
S7 C65 1.783(2) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
S8 O11 1.4898(19) . ?
S8 C66 1.788(3) . ?
S8 C67 1.787(3) . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
S9 O12 1.5150(15) . ?
S9 C68 1.777(2) . ?
S9 C69 1.783(2) . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 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 N3 107.22(9) . . ?
O2 S1 N4 115.21(9) . . ?
O2 S1 C14 110.33(9) . . ?
N3 S1 N4 112.66(9) . . ?
N3 S1 C14 113.16(9) . . ?
N4 S1 C14 98.23(9) . . ?
C11 N1 C7 118.08(17) . . ?
C9 N2 H2 122.4(17) . . ?
C9 N2 C11 121.76(17) . . ?
C11 N2 H2 115.7(17) . . ?
C11 N3 S1 120.57(14) . . ?
C12 N4 S1 111.62(14) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.7(2) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.9(2) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 119.97(18) . . ?
C5 C6 C1 119.20(18) . . ?
C5 C6 C7 120.83(18) . . ?
N1 C7 C6 116.45(17) . . ?
N1 C7 C8 121.99(17) . . ?
C8 C7 C6 121.56(18) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.49(18) . . ?
C9 C8 H8 120.8 . . ?
N2 C9 C8 118.15(18) . . ?
N2 C9 C10 117.17(18) . . ?
C8 C9 C10 124.67(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 N2 121.52(18) . . ?
N1 C11 N3 125.61(18) . . ?
N3 C11 N2 112.86(17) . . ?
O1 C12 N4 124.97(19) . . ?
O1 C12 C13 122.87(18) . . ?
N4 C12 C13 112.16(17) . . ?
C14 C13 C12 111.84(17) . . ?
C14 C13 C18 118.92(19) . . ?
C18 C13 C12 129.24(18) . . ?
C13 C14 S1 105.77(15) . . ?
C13 C14 C15 124.63(19) . . ?
C15 C14 S1 129.53(15) . . ?
C14 C15 H15 122.4 . . ?
C14 C15 C16 115.15(18) . . ?
C16 C15 H15 122.4 . . ?
C15 C16 Cl1 118.14(16) . . ?
C17 C16 Cl1 119.02(16) . . ?
C17 C16 C15 122.81(19) . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.61(18) . . ?
C18 C17 H17 120.2 . . ?
C13 C18 C17 118.87(19) . . ?
C13 C18 C19 121.1(2) . . ?
C17 C18 C19 120.00(19) . . ?
N5 C19 C18 177.5(2) . . ?
O4 S2 N8 106.61(9) . . ?
O4 S2 N9 114.46(10) . . ?
O4 S2 C33 111.85(9) . . ?
N8 S2 N9 115.15(9) . . ?
N8 S2 C33 110.22(9) . . ?
N9 S2 C33 98.49(9) . . ?
C30 N6 C26 117.93(16) . . ?
C28 N7 H7 121.9(18) . . ?
C28 N7 C30 121.86(17) . . ?
C30 N7 H7 116.3(18) . . ?
C30 N8 S2 121.92(14) . . ?
C31 N9 S2 111.57(14) . . ?
C21 C20 H20 119.6 . . ?
C21 C20 C25 120.74(18) . . ?
C25 C20 H20 119.6 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.36(19) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.53(19) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.39(19) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.65(19) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 118.31(18) . . ?
C20 C25 C26 120.17(17) . . ?
C24 C25 C26 121.47(18) . . ?
N6 C26 C25 115.86(17) . . ?
N6 C26 C27 122.02(17) . . ?
C27 C26 C25 122.12(17) . . ?
C26 C27 H27 120.9 . . ?
C28 C27 C26 118.25(18) . . ?
C28 C27 H27 120.9 . . ?
N7 C28 C27 118.36(18) . . ?
N7 C28 C29 116.96(18) . . ?
C27 C28 C29 124.68(18) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N6 C30 N7 121.55(17) . . ?
N6 C30 N8 125.76(18) . . ?
N8 C30 N7 112.69(17) . . ?
O3 C31 N9 125.35(19) . . ?
O3 C31 C32 122.48(18) . . ?
N9 C31 C32 112.16(17) . . ?
C33 C32 C31 111.73(17) . . ?
C33 C32 C37 118.24(18) . . ?
C37 C32 C31 130.00(18) . . ?
C32 C33 S2 105.92(14) . . ?
C32 C33 C34 124.88(18) . . ?
C34 C33 S2 129.13(16) . . ?
C33 C34 H34 122.2 . . ?
C33 C34 C35 115.54(19) . . ?
C35 C34 H34 122.2 . . ?
C34 C35 Cl2 119.25(17) . . ?
C36 C35 Cl2 118.44(16) . . ?
C36 C35 C34 122.3(2) . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.21(19) . . ?
C37 C36 H36 119.9 . . ?
C32 C37 C36 118.72(18) . . ?
C32 C37 C38 123.31(19) . . ?
C36 C37 C38 117.87(18) . . ?
N10 C38 C37 174.8(2) . . ?
O6 S3 N13 107.96(9) . . ?
O6 S3 N14 115.18(10) . . ?
O6 S3 C52 109.59(9) . . ?
N13 S3 N14 112.98(10) . . ?
N13 S3 C52 113.29(9) . . ?
N14 S3 C52 97.67(9) . . ?
C49 N11 C45 117.79(17) . . ?
C47 N12 H12 121.0(19) . . ?
C47 N12 C49 121.83(17) . . ?
C49 N12 H12 117.2(19) . . ?
C49 N13 S3 121.70(14) . . ?
C50 N14 S3 111.72(14) . . ?
C40 C39 H39 119.9 . . ?
C40 C39 C44 120.17(19) . . ?
C44 C39 H39 119.9 . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C41 120.65(19) . . ?
C41 C40 H40 119.7 . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.55(19) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C43 120.2(2) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 119.7 . . ?
C42 C43 C44 120.55(19) . . ?
C44 C43 H43 119.7 . . ?
C39 C44 C45 121.07(18) . . ?
C43 C44 C39 118.83(18) . . ?
C43 C44 C45 120.09(18) . . ?
N11 C45 C44 116.08(17) . . ?
N11 C45 C46 121.96(17) . . ?
C46 C45 C44 121.95(17) . . ?
C45 C46 H46 120.8 . . ?
C47 C46 C45 118.47(18) . . ?
C47 C46 H46 120.8 . . ?
N12 C47 C46 118.17(18) . . ?
N12 C47 C48 117.33(17) . . ?
C46 C47 C48 124.49(18) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N11 C49 N12 121.75(17) . . ?
N11 C49 N13 125.35(18) . . ?
N13 C49 N12 112.85(17) . . ?
O5 C50 N14 125.2(2) . . ?
O5 C50 C51 121.9(2) . . ?
N14 C50 C51 112.90(17) . . ?
C52 C51 C50 111.30(18) . . ?
C52 C51 C56 118.91(19) . . ?
C56 C51 C50 129.79(19) . . ?
C51 C52 S3 106.34(14) . . ?
C51 C52 C53 123.87(19) . . ?
C53 C52 S3 129.75(15) . . ?
C52 C53 H53 121.9 . . ?
C52 C53 C54 116.13(19) . . ?
C54 C53 H53 121.9 . . ?
C53 C54 Cl3 118.50(16) . . ?
C55 C54 Cl3 119.09(16) . . ?
C55 C54 C53 122.40(19) . . ?
C54 C55 H55 120.4 . . ?
C54 C55 C56 119.16(19) . . ?
C56 C55 H55 120.4 . . ?
C51 C56 C55 119.50(19) . . ?
C51 C56 C57 121.3(2) . . ?
C55 C56 C57 119.2(2) . . ?
N15 C57 C56 177.1(3) . . ?
O7 S4 C58 105.88(11) . . ?
O7 S4 C59 105.87(11) . . ?
C59 S4 C58 96.81(12) . . ?
S4 C58 H58A 109.5 . . ?
S4 C58 H58B 109.5 . . ?
S4 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
S4 C59 H59A 109.5 . . ?
S4 C59 H59B 109.5 . . ?
S4 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
O8 S5 C60 105.93(12) . . ?
O8 S5 C61 106.51(12) . . ?
C60 S5 C61 97.13(13) . . ?
S5 C60 H60A 109.5 . . ?
S5 C60 H60B 109.5 . . ?
S5 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
S5 C61 H61A 109.5 . . ?
S5 C61 H61B 109.5 . . ?
S5 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
O9 S6 C62 106.47(10) . . ?
O9 S6 C63 104.82(11) . . ?
C62 S6 C63 97.80(12) . . ?
S6 C62 H62A 109.5 . . ?
S6 C62 H62B 109.5 . . ?
S6 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
S6 C63 H63A 109.5 . . ?
S6 C63 H63B 109.5 . . ?
S6 C63 H63C 109.5 . . ?
H63A C63 H63B 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
O10 S7 C64 103.11(9) . . ?
O10 S7 C65 105.81(9) . . ?
C65 S7 C64 98.43(10) . . ?
S7 C64 H64A 109.5 . . ?
S7 C64 H64B 109.5 . . ?
S7 C64 H64C 109.5 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
S7 C65 H65A 109.5 . . ?
S7 C65 H65B 109.5 . . ?
S7 C65 H65C 109.5 . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
O11 S8 C66 106.69(12) . . ?
O11 S8 C67 106.40(12) . . ?
C67 S8 C66 97.38(12) . . ?
S8 C66 H66A 109.5 . . ?
S8 C66 H66B 109.5 . . ?
S8 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
S8 C67 H67A 109.5 . . ?
S8 C67 H67B 109.5 . . ?
S8 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
O12 S9 C68 103.94(10) . . ?
O12 S9 C69 105.71(9) . . ?
C68 S9 C69 99.48(11) . . ?
S9 C68 H68A 109.5 . . ?
S9 C68 H68B 109.5 . . ?
S9 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
S9 C69 H69A 109.5 . . ?
S9 C69 H69B 109.5 . . ?
S9 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 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
Cl1 C16 C17 C18 178.08(15) . . . . ?
S1 N3 C11 N1 -15.8(3) . . . . ?
S1 N3 C11 N2 165.36(14) . . . . ?
S1 N4 C12 O1 -173.42(17) . . . . ?
S1 N4 C12 C13 6.8(2) . . . . ?
S1 C14 C15 C16 176.41(15) . . . . ?
O1 C12 C13 C14 175.05(19) . . . . ?
O1 C12 C13 C18 -5.9(3) . . . . ?
O2 S1 N3 C11 -172.13(15) . . . . ?
O2 S1 N4 C12 -122.47(14) . . . . ?
O2 S1 C14 C13 123.05(14) . . . . ?
O2 S1 C14 C15 -53.9(2) . . . . ?
N1 C7 C8 C9 0.8(3) . . . . ?
N3 S1 N4 C12 114.08(15) . . . . ?
N3 S1 C14 C13 -116.83(14) . . . . ?
N3 S1 C14 C15 66.2(2) . . . . ?
N4 S1 N3 C11 -44.34(18) . . . . ?
N4 S1 C14 C13 2.21(15) . . . . ?
N4 S1 C14 C15 -174.72(19) . . . . ?
N4 C12 C13 C14 -5.1(2) . . . . ?
N4 C12 C13 C18 173.88(19) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C6 C7 N1 -11.0(3) . . . . ?
C1 C6 C7 C8 168.47(19) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C6 C7 179.6(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -178.71(18) . . . . ?
C5 C6 C7 N1 168.79(17) . . . . ?
C5 C6 C7 C8 -11.8(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C7 C8 C9 -178.55(18) . . . . ?
C7 N1 C11 N2 0.3(3) . . . . ?
C7 N1 C11 N3 -178.37(18) . . . . ?
C7 C8 C9 N2 -0.2(3) . . . . ?
C7 C8 C9 C10 178.78(19) . . . . ?
C9 N2 C11 N1 0.3(3) . . . . ?
C9 N2 C11 N3 179.20(17) . . . . ?
C11 N1 C7 C6 178.50(16) . . . . ?
C11 N1 C7 C8 -0.9(3) . . . . ?
C11 N2 C9 C8 -0.4(3) . . . . ?
C11 N2 C9 C10 -179.44(18) . . . . ?
C12 C13 C14 S1 1.3(2) . . . . ?
C12 C13 C14 C15 178.41(18) . . . . ?
C12 C13 C18 C17 -177.85(19) . . . . ?
C12 C13 C18 C19 0.1(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 S1 N3 C11 65.98(18) . . . . ?
C14 S1 N4 C12 -5.32(16) . . . . ?
C14 C13 C18 C17 1.1(3) . . . . ?
C14 C13 C18 C19 179.05(19) . . . . ?
C14 C15 C16 Cl1 -177.69(15) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C13 -0.8(3) . . . . ?
C16 C17 C18 C19 -178.80(19) . . . . ?
C18 C13 C14 S1 -177.82(15) . . . . ?
C18 C13 C14 C15 -0.7(3) . . . . ?
Cl2 C35 C36 C37 -179.97(16) . . . . ?
S2 N8 C30 N6 -3.1(3) . . . . ?
S2 N8 C30 N7 177.06(13) . . . . ?
S2 N9 C31 O3 179.66(16) . . . . ?
S2 N9 C31 C32 0.5(2) . . . . ?
S2 C33 C34 C35 -177.34(16) . . . . ?
O3 C31 C32 C33 -177.03(18) . . . . ?
O3 C31 C32 C37 5.2(3) . . . . ?
O4 S2 N8 C30 -175.47(16) . . . . ?
O4 S2 N9 C31 -121.01(14) . . . . ?
O4 S2 C33 C32 124.13(14) . . . . ?
O4 S2 C33 C34 -58.8(2) . . . . ?
N6 C26 C27 C28 -0.9(3) . . . . ?
N8 S2 N9 C31 114.90(14) . . . . ?
N8 S2 C33 C32 -117.44(14) . . . . ?
N8 S2 C33 C34 59.6(2) . . . . ?
N9 S2 N8 C30 -47.35(19) . . . . ?
N9 S2 C33 C32 3.41(15) . . . . ?
N9 S2 C33 C34 -179.51(19) . . . . ?
N9 C31 C32 C33 2.2(2) . . . . ?
N9 C31 C32 C37 -175.63(19) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
C20 C25 C26 N6 -6.5(3) . . . . ?
C20 C25 C26 C27 174.07(18) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C21 C20 C25 C26 177.97(18) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C24 C25 C20 -0.5(3) . . . . ?
C23 C24 C25 C26 -177.89(19) . . . . ?
C24 C25 C26 N6 170.86(18) . . . . ?
C24 C25 C26 C27 -8.6(3) . . . . ?
C25 C20 C21 C22 0.4(3) . . . . ?
C25 C26 C27 C28 178.46(17) . . . . ?
C26 N6 C30 N7 -1.6(3) . . . . ?
C26 N6 C30 N8 178.55(18) . . . . ?
C26 C27 C28 N7 -0.7(3) . . . . ?
C26 C27 C28 C29 178.43(19) . . . . ?
C28 N7 C30 N6 0.0(3) . . . . ?
C28 N7 C30 N8 179.87(17) . . . . ?
C30 N6 C26 C25 -177.35(16) . . . . ?
C30 N6 C26 C27 2.1(3) . . . . ?
C30 N7 C28 C27 1.1(3) . . . . ?
C30 N7 C28 C29 -178.05(18) . . . . ?
C31 C32 C33 S2 -3.43(19) . . . . ?
C31 C32 C33 C34 179.34(18) . . . . ?
C31 C32 C37 C36 -178.97(19) . . . . ?
C31 C32 C37 C38 4.6(3) . . . . ?
C32 C33 C34 C35 -0.8(3) . . . . ?
C33 S2 N8 C30 62.94(18) . . . . ?
C33 S2 N9 C31 -2.24(15) . . . . ?
C33 C32 C37 C36 3.4(3) . . . . ?
C33 C32 C37 C38 -173.02(18) . . . . ?
C33 C34 C35 Cl2 -179.27(15) . . . . ?
C33 C34 C35 C36 3.4(3) . . . . ?
C34 C35 C36 C37 -2.6(3) . . . . ?
C35 C36 C37 C32 -0.9(3) . . . . ?
C35 C36 C37 C38 175.67(19) . . . . ?
C37 C32 C33 S2 174.65(15) . . . . ?
C37 C32 C33 C34 -2.6(3) . . . . ?
Cl3 C54 C55 C56 178.90(15) . . . . ?
S3 N13 C49 N11 -12.9(3) . . . . ?
S3 N13 C49 N12 169.46(14) . . . . ?
S3 N14 C50 O5 -177.42(17) . . . . ?
S3 N14 C50 C51 2.3(2) . . . . ?
S3 C52 C53 C54 176.04(15) . . . . ?
O5 C50 C51 C52 176.78(19) . . . . ?
O5 C50 C51 C56 -2.8(3) . . . . ?
O6 S3 N13 C49 177.94(16) . . . . ?
O6 S3 N14 C50 -116.86(15) . . . . ?
O6 S3 C52 C51 119.43(14) . . . . ?
O6 S3 C52 C53 -58.3(2) . . . . ?
N11 C45 C46 C47 1.4(3) . . . . ?
N13 S3 N14 C50 118.43(15) . . . . ?
N13 S3 C52 C51 -119.93(14) . . . . ?
N13 S3 C52 C53 62.3(2) . . . . ?
N14 S3 N13 C49 -53.51(19) . . . . ?
N14 S3 C52 C51 -0.80(15) . . . . ?
N14 S3 C52 C53 -178.52(19) . . . . ?
N14 C50 C51 C52 -3.0(2) . . . . ?
N14 C50 C51 C56 177.48(19) . . . . ?
C39 C40 C41 C42 -0.3(3) . . . . ?
C39 C44 C45 N11 -174.48(17) . . . . ?
C39 C44 C45 C46 4.4(3) . . . . ?
C40 C39 C44 C43 0.0(3) . . . . ?
C40 C39 C44 C45 178.96(18) . . . . ?
C40 C41 C42 C43 0.2(3) . . . . ?
C41 C42 C43 C44 -0.1(3) . . . . ?
C42 C43 C44 C39 0.0(3) . . . . ?
C42 C43 C44 C45 -179.01(19) . . . . ?
C43 C44 C45 N11 4.5(3) . . . . ?
C43 C44 C45 C46 -176.68(18) . . . . ?
C44 C39 C40 C41 0.1(3) . . . . ?
C44 C45 C46 C47 -177.42(17) . . . . ?
C45 N11 C49 N12 1.1(3) . . . . ?
C45 N11 C49 N13 -176.26(18) . . . . ?
C45 C46 C47 N12 -0.2(3) . . . . ?
C45 C46 C47 C48 178.29(18) . . . . ?
C47 N12 C49 N11 0.0(3) . . . . ?
C47 N12 C49 N13 177.72(17) . . . . ?
C49 N11 C45 C44 177.03(16) . . . . ?
C49 N11 C45 C46 -1.8(3) . . . . ?
C49 N12 C47 C46 -0.5(3) . . . . ?
C49 N12 C47 C48 -179.08(17) . . . . ?
C50 C51 C52 S3 2.13(19) . . . . ?
C50 C51 C52 C53 -179.99(18) . . . . ?
C50 C51 C56 C55 -178.76(19) . . . . ?
C50 C51 C56 C57 2.5(3) . . . . ?
C51 C52 C53 C54 -1.3(3) . . . . ?
C52 S3 N13 C49 56.39(19) . . . . ?
C52 S3 N14 C50 -0.94(16) . . . . ?
C52 C51 C56 C55 1.7(3) . . . . ?
C52 C51 C56 C57 -177.05(19) . . . . ?
C52 C53 C54 Cl3 -177.63(15) . . . . ?
C52 C53 C54 C55 1.7(3) . . . . ?
C53 C54 C55 C56 -0.5(3) . . . . ?
C54 C55 C56 C51 -1.3(3) . . . . ?
C54 C55 C56 C57 177.49(19) . . . . ?
C56 C51 C52 S3 -178.28(15) . . . . ?
C56 C51 C52 C53 -0.4(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_283
_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 1.997
_oxdiff_exptl_absorpt_empirical_full_min 0.604
####################################################################### 
# 
# 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_en13222-97-meoh_op
_database_code_depnum_ccdc_archive 'CCDC 2517065'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        'AZ14288800 SN1088856581'
_chemical_formula_moiety         'C18 H12 Cl F N4 O2 S'
_chemical_formula_sum            'C18 H12 Cl F N4 O2 S'
_chemical_formula_weight         402.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H12ClFN4O2S
_chemical_oxdiff_usercomment     'Mario crystal'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.27110(10)
_cell_length_b                   12.39990(10)
_cell_length_c                   13.04290(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.5040(10)
_cell_angle_gamma                90
_cell_volume                     3470.85(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28294
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      77.2100
_cell_measurement_theta_min      4.0970
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.461
_exptl_absorpt_coefficient_mu    3.373
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-12 0 -3 0.1273
7 -4 -7 0.0131
-7 4 7 0.0560
11 0 3 0.1407
6 6 -6 0.0452
-6 -6 6 0.0086
0 8 0 0.0589

_exptl_crystal_preparation       'Slow evaporation from methanol'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.054
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.0000 -0.0000 -3.0000 0.0174 0.0009 1.0225
7.0000 -4.0000 -7.0000 0.8139 -0.5856 0.0176
-7.0000 4.0000 7.0000 -0.8139 0.5856 -0.0176
11.0000 -0.0000 3.0000 -0.0266 0.0218 -0.9551
6.0000 6.0000 -6.0000 -0.3681 -0.9882 0.0336
-6.0000 -6.0000 6.0000 0.3681 0.9882 -0.0336
-0.0000 8.0000 0.0000 -0.9043 -0.4125 0.0157

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            50698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.411
_diffrn_reflns_theta_min         4.118
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 137.00   0.50    0.05    --   66.00  76.00 139.70  202
  2  ω     35.00 137.00   0.50    0.05    --   66.00  77.00  61.79  204
  3  ω     40.00 141.00   0.50    0.05    --   70.00  76.00 -19.03  202
  4  ω     43.00 145.00   0.50    0.05    --   74.00  77.00 -78.28  204
  5  ω     40.00 141.00   0.50    0.05    --   70.00  76.00-120.59  202
  6  ω     36.00 138.00   0.50    0.05    --   66.00  75.00-169.35  204
  7  ω     60.00 162.00   0.50    0.19    --   90.00  75.00-125.74  204
  8  ω     89.00 178.00   0.50    0.19    --  108.71  45.00-150.00  178
  9  ω     89.00 178.00   0.50    0.19    --  108.71  45.00 -30.00  178
 10  ω     67.00 178.00   0.50    0.19    --   98.01  30.00  60.00  222
 11  ω    -26.00  34.00   0.50    0.05    --  -48.82  19.00   0.00  120
 12  ω    -35.00   0.00   0.50    0.19    --  -82.38  30.00  60.00   70
 13  ω    -35.00   0.00   0.50    0.19    --  -82.38  30.00  90.00   70
 14  ω    -26.00  34.00   0.50    0.05    --  -48.82  19.00  60.00  120
 15  ω    -35.00   0.00   0.50    0.19    --  -82.38  30.00  30.00   70
 16  ω    -35.00   0.00   0.50    0.19    --  -82.38  30.00   0.00   70
 17  ω    -35.00   0.00   0.50    0.19    --  -82.38  30.00 -90.00   70
 18  ω    -51.00  -1.00   0.50    0.19    --  -82.38  45.00-150.00  100
 19  ω     17.00  43.00   0.50    0.05    --   54.00  88.00   0.88   52
 20  ω     95.00 176.00   0.50    0.19    --   98.01 125.00-180.00  162
 21  ω     87.00 178.00   0.50    0.19    --  108.71 137.00-123.00  182
 22  ω     95.00 178.00   0.50    0.19    --  108.71 125.00-150.00  166
 23  ω     90.00 175.00   0.50    0.19    --   98.01 133.00  58.00  170
 24  ω     95.00 176.00   0.50    0.19    --   98.01 125.00   0.00  162
 25  ω     90.00 178.00   0.50    0.19    --  108.71 133.00  58.00  176
 26  ω     15.00  42.00   0.50    0.05    --   54.00  91.00 149.78   54
 27  ω     15.00  42.00   0.50    0.05    --   54.00  91.00  65.10   54
 28  ω    -50.00 -17.00   0.50    0.05    --   14.00 132.00  33.15   66
 29  ω     14.00  41.00   0.50    0.05    --   54.00  92.00 -47.75   54
 30  ω     15.00  42.00   0.50    0.05    --   54.00  91.00-163.74   54
 31  ω     16.00  43.00   0.50    0.05    --   54.00  89.00-122.27   54
 32  ω     17.00  51.00   0.50    0.19    --   98.01 -45.00 -60.00   68
 33  ω     32.00  71.00   0.50    0.19    --  108.71 -61.00-120.00   78
 34  ω     32.00  71.00   0.50    0.19    --  108.71 -61.00-180.00   78
 35  ω     32.00  71.00   0.50    0.19    --  108.71 -61.00 -30.00   78
 36  ω     17.00  51.00   0.50    0.19    --   98.01 -45.00 -30.00   68
 37  ω     17.00  51.00   0.50    0.19    --   98.01 -45.00   0.00   68
 38  ω     17.00  51.00   0.50    0.19    --   98.01 -45.00  60.00   68
 39  ω     17.00  51.00   0.50    0.19    --   98.01 -45.00 120.00   68
 40  ω     38.00 105.00   0.50    0.19    --  108.71 -77.00 -30.00  134
 41  ω     17.00  51.00   0.50    0.19    --   98.01 -45.00-180.00   68
 42  ω     35.00 105.00   0.50    0.19    --  108.71 -95.00-180.00  140
 43  ω     39.00 113.00   0.50    0.05    --   48.20-133.00  -9.00  148
 44  ω     39.00 117.00   0.50    0.19    --   98.01-133.00  -9.00  156
 45  ω     34.00 112.00   0.50    0.19    --   98.01-125.00-120.00  156
 46  ω     39.00 118.00   0.50    0.19    --  108.71-133.00  -9.00  158
 47  ω     34.00 111.00   0.50    0.19    --  108.71-125.00-180.00  154
 48  ω     34.00 112.00   0.50    0.19    --   98.01-125.00  30.00  156
 49  ω     41.00 120.00   0.50    0.19    --   98.01-137.00 173.00  158
 50  ω     41.00 121.00   0.50    0.19    --  108.71-137.00 173.00  160
 51  ω   -125.00 -66.00   0.50    0.05    --  -48.82-137.00 173.00  118
 52  ω   -158.00 -66.00   0.50    0.19    --  -82.38-137.00 173.00  184
 53  ω   -159.00 -68.00   0.50    0.19    --  -82.38-133.00  -9.00  182
 54  ω   -125.00 -68.00   0.50    0.05    --  -48.82-133.00  -9.00  114
 55  ω   -163.00 -61.00   0.50    0.19    --  -90.25 -73.00 110.45  204
 56  ω   -162.00 -61.00   0.50    0.19    --  -90.25 -74.00 173.75  202
 57  ω   -153.00 -51.00   0.50    0.19    --  -82.38 -77.00   0.00  204
 58  ω   -162.00 -60.00   0.50    0.19    --  -90.25 -75.00 -60.55  204
 59  ω   -163.00 -61.00   0.50    0.19    --  -90.25 -73.00  61.63  204
 60  ω   -163.00-121.00   0.50    0.19    --  -90.25 -73.00 149.61   84
 61  ω    -92.00 -17.00   0.50    0.19    --  -82.38 133.00  58.00  150
 62  ω    -92.00 -17.00   0.50    0.05    --  -48.82 133.00  58.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091736000
_diffrn_orient_matrix_UB_12      -0.1130321000
_diffrn_orient_matrix_UB_13      -0.0425050000
_diffrn_orient_matrix_UB_21      -0.0226873000
_diffrn_orient_matrix_UB_22      -0.0515680000
_diffrn_orient_matrix_UB_23      0.0904399000
_diffrn_orient_matrix_UB_31      -0.0674417000
_diffrn_orient_matrix_UB_32      0.0019666000
_diffrn_orient_matrix_UB_33      -0.0710783000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3397
_reflns_number_total             3647
_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 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_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         0.270
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00023(4)
_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   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     147
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.106
_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)+(0.0471P)²+2.2003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          
'C13-C14-F1-C15-C16-Cl1-C17 were refined as disorder with occupancy approximately 0.65: 0.35'
_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. Restrained distances
 C18-C13A = C13A-C14A = C14A-C15A = C15A-C16A = C16A-C17A = C17A-C18
 1.39 with sigma of 0.01
 C6-C1 = C1-C2 = C2-C3 = C3-C4 = C4-C5 = C5-C6
 1.39 with sigma of 0.01
 C6-C2 \\sim C1-C3 \\sim C2-C4 \\sim C3-C5 \\sim C4-C6 \\sim C5-C1
 with sigma of 0.02
 C18-C14A \\sim C13A-C15A \\sim C14A-C16A \\sim C15A-C17A \\sim C16A-C18 \\sim
C17A-C13A
 with sigma of 0.02
3. Restrained planarity
 C6, C1, C2, C3, C4, C5
 with sigma of 0.1
 C18, C13A, C14A, C15A, C16A, C17A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C13A \\sim C13B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Uanis(C18) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 Cl1A, C16A, C14A, F1A, C15A, C13A, C17A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl1B, C15B, C13B, C18, C14B, C17B, F1B, C16B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(Cl1B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(C15B)=Sof(H15B)=Sof(C14B)=
 Sof(C13B)=Sof(F1B)=1-FVAR(1)
 Sof(Cl1A)=Sof(F1A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(C15A)=Sof(H15A)=
 Sof(C14A)=Sof(C13A)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C17A(H17A), C15A(H15A), C5(H5), C1(H1A), C4(H4), C3(H3), C2(H2),
 C17B(H17B), C15B(H15B)
7.b Fitted hexagon refined as free rotating group:
 C18(C17B,C16B,C15B,C14B,C13B)
7.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32219(2) 0.67062(3) 0.21620(2) 0.02728(11) Uani 1 1 d . . . . .
Cl1A Cl 0.5449(2) 0.4697(4) 0.4006(4) 0.0597(7) Uani 0.644(19) 1 d . . P A 1
O2 O 0.32124(5) 0.64544(9) 0.10827(8) 0.0402(2) Uani 1 1 d . . . . .
O1 O 0.37021(5) 0.93948(8) 0.31213(8) 0.0395(2) Uani 1 1 d . . . . .
F1A F 0.5044(3) 0.8667(5) 0.4206(6) 0.0540(10) Uani 0.644(19) 1 d . . P A 1
N2 N 0.30517(5) 0.64800(8) 0.43200(8) 0.0255(2) Uani 1 1 d . . . . .
N1 N 0.22016(5) 0.53280(9) 0.36158(9) 0.0289(2) Uani 1 1 d . . . . .
N4 N 0.31230(5) 0.79476(9) 0.23607(9) 0.0301(2) Uani 1 1 d . . . . .
N3 N 0.27422(5) 0.59550(9) 0.24955(9) 0.0305(2) Uani 1 1 d . . . . .
C11 C 0.26815(6) 0.59567(10) 0.35001(10) 0.0258(3) Uani 1 1 d . . . . .
C7 C 0.29393(6) 0.63705(10) 0.52793(10) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.33561(6) 0.69643(11) 0.61758(10) 0.0286(3) Uani 1 1 d D . . . .
C8 C 0.24545(6) 0.57278(11) 0.54277(10) 0.0301(3) Uani 1 1 d . . . . .
H8 H 0.238153 0.566677 0.611046 0.036 Uiso 1 1 calc R U . . .
C17A C 0.4337(3) 0.5651(3) 0.3168(5) 0.0333(8) Uani 0.644(19) 1 d D . P A 1
H17A H 0.416494 0.496491 0.292961 0.040 Uiso 0.644(19) 1 calc R U P A 1
C16A C 0.4954(3) 0.5797(5) 0.3733(6) 0.0387(9) Uani 0.644(19) 1 d D . P A 1
C15A C 0.52030(17) 0.6790(7) 0.4076(5) 0.0401(10) Uani 0.644(19) 1 d D . P A 1
H15A H 0.563223 0.685717 0.443818 0.048 Uiso 0.644(19) 1 calc R U P A 1
C14A C 0.48212(18) 0.7691(5) 0.3888(6) 0.0352(9) Uani 0.644(19) 1 d D . P A 1
C13A C 0.41983(15) 0.7615(2) 0.3332(4) 0.0288(4) Uani 0.644(19) 1 d D U P A 1
C9 C 0.20861(7) 0.51875(11) 0.45745(11) 0.0314(3) Uani 1 1 d . . . . .
C5 C 0.32907(7) 0.68722(13) 0.72089(11) 0.0367(3) Uani 1 1 d D . . . .
H5 H 0.298435 0.640228 0.734624 0.044 Uiso 1 1 calc R U . . .
C1 C 0.38144(7) 0.76532(13) 0.59958(12) 0.0381(3) Uani 1 1 d D . . . .
H1A H 0.386787 0.772081 0.530010 0.046 Uiso 1 1 calc R U . . .
C10 C 0.15740(8) 0.44385(14) 0.46410(13) 0.0453(4) Uani 1 1 d . . . . .
H10A H 0.121624 0.454622 0.402208 0.068 Uiso 1 1 calc R U . . .
H10B H 0.144942 0.458528 0.529336 0.068 Uiso 1 1 calc R U . . .
H10C H 0.171979 0.369193 0.465111 0.068 Uiso 1 1 calc R U . . .
C4 C 0.36696(8) 0.74615(15) 0.80330(12) 0.0465(4) Uani 1 1 d D . . . .
H4 H 0.361972 0.739464 0.873116 0.056 Uiso 1 1 calc R U . . .
C3 C 0.41183(8) 0.81442(16) 0.78507(13) 0.0513(4) Uani 1 1 d D . . . .
H3 H 0.437610 0.854795 0.841911 0.062 Uiso 1 1 calc R U . . .
C2 C 0.41906(8) 0.82374(16) 0.68274(14) 0.0503(4) Uani 1 1 d D . . . .
H2 H 0.450032 0.870513 0.669835 0.060 Uiso 1 1 calc R U . . .
Cl1B Cl 0.5568(3) 0.5026(11) 0.4270(7) 0.0632(16) Uani 0.356(19) 1 d . . P A 2
C12 C 0.36550(6) 0.84173(11) 0.29339(10) 0.0291(3) Uani 1 1 d . . . . .
C18 C 0.39951(6) 0.65931(11) 0.29849(10) 0.0292(3) Uani 1 1 d DG U . . .
C17B C 0.4439(2) 0.5786(4) 0.3297(7) 0.0356(15) Uani 0.356(19) 1 d G . P A 2
H17B H 0.433105 0.505563 0.311640 0.043 Uiso 0.356(19) 1 calc R U P A 2
C16B C 0.5042(2) 0.6046(8) 0.3873(10) 0.0368(17) Uani 0.356(19) 1 d G . P A 2
C15B C 0.5201(2) 0.7114(10) 0.4137(9) 0.0383(17) Uani 0.356(19) 1 d G . P A 2
H15B H 0.561284 0.729202 0.453067 0.046 Uiso 0.356(19) 1 calc R U P A 2
C14B C 0.4757(4) 0.7922(7) 0.3825(10) 0.0335(15) Uani 0.356(19) 1 d G . P A 2
C13B C 0.4154(3) 0.7661(2) 0.3249(7) 0.0287(5) Uani 0.356(19) 1 d G U P A 2
F1B F 0.4960(6) 0.8942(9) 0.4175(12) 0.0564(18) Uani 0.356(19) 1 d . . P A 2
H1 H 0.1952(9) 0.4998(15) 0.3022(16) 0.045(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4366(10) . ?
S1 N4 1.5861(12) . ?
S1 N3 1.5642(11) . ?
S1 C18 1.7746(13) . ?
Cl1A C16A 1.730(4) . ?
O1 C12 1.2354(17) . ?
F1A C14A 1.331(4) . ?
N2 C11 1.3316(17) . ?
N2 C7 1.3468(15) . ?
N1 C11 1.3634(16) . ?
N1 C9 1.3535(16) . ?
N1 H1 0.92(2) . ?
N4 C12 1.3521(18) . ?
N3 C11 1.3527(16) . ?
C7 C6 1.4803(18) . ?
C7 C8 1.3964(18) . ?
C6 C5 1.3982(18) . ?
C6 C1 1.398(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.368(2) . ?
C17A H17A 0.9500 . ?
C17A C16A 1.386(4) . ?
C17A C18 1.380(3) . ?
C16A C15A 1.376(4) . ?
C15A H15A 0.9500 . ?
C15A C14A 1.386(4) . ?
C14A C13A 1.386(3) . ?
C13A C12 1.545(3) . ?
C13A C18 1.380(3) . ?
C9 C10 1.4911(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.384(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.385(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.391(2) . ?
C2 H2 0.9500 . ?
Cl1B C16B 1.707(6) . ?
C12 C13B 1.427(6) . ?
C18 C17B 1.3900 . ?
C18 C13B 1.3900 . ?
C17B H17B 0.9500 . ?
C17B C16B 1.3900 . ?
C16B C15B 1.3900 . ?
C15B H15B 0.9500 . ?
C15B C14B 1.3900 . ?
C14B C13B 1.3900 . ?
C14B F1B 1.380(8) . ?

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 N4 113.88(6) . . ?
O2 S1 N3 108.11(6) . . ?
O2 S1 C18 109.46(6) . . ?
N4 S1 C18 97.62(6) . . ?
N3 S1 N4 113.43(6) . . ?
N3 S1 C18 114.16(6) . . ?
C11 N2 C7 117.90(11) . . ?
C11 N1 H1 118.4(12) . . ?
C9 N1 C11 121.61(12) . . ?
C9 N1 H1 120.0(12) . . ?
C12 N4 S1 111.65(9) . . ?
C11 N3 S1 121.39(9) . . ?
N2 C11 N1 121.67(11) . . ?
N2 C11 N3 125.31(11) . . ?
N3 C11 N1 112.99(11) . . ?
N2 C7 C6 116.78(11) . . ?
N2 C7 C8 121.93(12) . . ?
C8 C7 C6 121.28(11) . . ?
C5 C6 C7 121.05(12) . . ?
C1 C6 C7 120.21(12) . . ?
C1 C6 C5 118.72(13) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.97(12) . . ?
C9 C8 H8 120.5 . . ?
C16A C17A H17A 123.1 . . ?
C18 C17A H17A 123.1 . . ?
C18 C17A C16A 113.8(3) . . ?
C17A C16A Cl1A 119.6(3) . . ?
C15A C16A Cl1A 117.3(3) . . ?
C15A C16A C17A 123.1(3) . . ?
C16A C15A H15A 120.4 . . ?
C16A C15A C14A 119.3(2) . . ?
C14A C15A H15A 120.4 . . ?
F1A C14A C15A 121.2(3) . . ?
F1A C14A C13A 117.6(4) . . ?
C15A C14A C13A 121.2(3) . . ?
C14A C13A C12 135.7(3) . . ?
C18 C13A C14A 115.4(3) . . ?
C18 C13A C12 108.8(2) . . ?
N1 C9 C8 117.88(12) . . ?
N1 C9 C10 118.11(12) . . ?
C8 C9 C10 124.01(12) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.41(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 C6 120.28(14) . . ?
C2 C1 H1A 119.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.66(15) . . ?
C3 C4 H4 119.7 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.47(15) . . ?
C2 C3 H3 120.3 . . ?
C1 C2 C3 120.46(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O1 C12 N4 123.19(13) . . ?
O1 C12 C13A 123.23(15) . . ?
O1 C12 C13B 124.69(17) . . ?
N4 C12 C13A 113.57(13) . . ?
N4 C12 C13B 112.06(16) . . ?
C17A C18 S1 124.9(3) . . ?
C13A C18 S1 107.81(16) . . ?
C13A C18 C17A 127.1(3) . . ?
C17B C18 S1 137.2(3) . . ?
C17B C18 C13B 120.0 . . ?
C13B C18 S1 102.5(3) . . ?
C18 C17B H17B 120.0 . . ?
C18 C17B C16B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C16B Cl1B 118.5(4) . . ?
C15B C16B Cl1B 121.5(4) . . ?
C15B C16B C17B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B C16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C15B C14B C13B 120.0 . . ?
F1B C14B C15B 114.8(6) . . ?
F1B C14B C13B 125.2(6) . . ?
C18 C13B C12 115.3(4) . . ?
C14B C13B C12 124.6(4) . . ?
C14B C13B C18 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 N4 C12 O1 174.65(10) . . . . ?
S1 N4 C12 C13A -5.3(3) . . . . ?
S1 N4 C12 C13B -2.8(4) . . . . ?
S1 N3 C11 N2 -7.73(18) . . . . ?
S1 N3 C11 N1 174.13(9) . . . . ?
S1 C18 C17B C16B 172.0(4) . . . . ?
S1 C18 C13B C12 8.4(7) . . . . ?
S1 C18 C13B C14B -174.4(3) . . . . ?
Cl1A C16A C15A C14A -179.1(5) . . . . ?
O2 S1 N4 C12 -108.32(10) . . . . ?
O2 S1 N3 C11 175.23(10) . . . . ?
O2 S1 C18 C17A -63.7(3) . . . . ?
O2 S1 C18 C13A 112.0(3) . . . . ?
O2 S1 C18 C17B -62.9(6) . . . . ?
O2 S1 C18 C13B 110.0(4) . . . . ?
O1 C12 C13B C18 178.1(4) . . . . ?
O1 C12 C13B C14B 1.2(6) . . . . ?
F1A C14A C13A C12 1.4(6) . . . . ?
F1A C14A C13A C18 177.7(6) . . . . ?
N2 C7 C6 C5 -177.74(11) . . . . ?
N2 C7 C6 C1 3.95(17) . . . . ?
N2 C7 C8 C9 0.51(19) . . . . ?
N4 S1 N3 C11 -57.48(12) . . . . ?
N4 S1 C18 C17A 177.6(3) . . . . ?
N4 S1 C18 C13A -6.7(3) . . . . ?
N4 S1 C18 C17B 178.4(6) . . . . ?
N4 S1 C18 C13B -8.8(4) . . . . ?
N4 C12 C13B C18 -4.5(8) . . . . ?
N4 C12 C13B C14B 178.6(3) . . . . ?
N3 S1 N4 C12 127.46(9) . . . . ?
N3 S1 C18 C17A 57.6(3) . . . . ?
N3 S1 C18 C13A -126.7(3) . . . . ?
N3 S1 C18 C17B 58.4(6) . . . . ?
N3 S1 C18 C13B -128.7(4) . . . . ?
C11 N2 C7 C6 -179.76(10) . . . . ?
C11 N2 C7 C8 0.34(17) . . . . ?
C11 N1 C9 C8 2.18(19) . . . . ?
C11 N1 C9 C10 -176.68(13) . . . . ?
C7 N2 C11 N1 0.07(17) . . . . ?
C7 N2 C11 N3 -177.92(12) . . . . ?
C7 C6 C5 C4 -177.72(13) . . . . ?
C7 C6 C1 C2 177.79(13) . . . . ?
C7 C8 C9 N1 -1.73(19) . . . . ?
C7 C8 C9 C10 177.06(14) . . . . ?
C6 C7 C8 C9 -179.39(12) . . . . ?
C6 C5 C4 C3 -0.3(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C8 C7 C6 C5 2.16(18) . . . . ?
C8 C7 C6 C1 -176.16(13) . . . . ?
C17A C16A C15A C14A 2.3(4) . . . . ?
C16A C17A C18 S1 172.5(3) . . . . ?
C16A C17A C18 C13A -2.5(3) . . . . ?
C16A C15A C14A F1A -179.9(6) . . . . ?
C16A C15A C14A C13A -2.1(4) . . . . ?
C15A C14A C13A C12 -176.5(6) . . . . ?
C15A C14A C13A C18 -0.3(3) . . . . ?
C14A C13A C12 O1 -3.3(5) . . . . ?
C14A C13A C12 N4 176.6(3) . . . . ?
C14A C13A C18 S1 -172.9(2) . . . . ?
C14A C13A C18 C17A 2.7(3) . . . . ?
C9 N1 C11 N2 -1.38(19) . . . . ?
C9 N1 C11 N3 176.84(12) . . . . ?
C5 C6 C1 C2 -0.6(2) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C1 C6 C5 C4 0.6(2) . . . . ?
C4 C3 C2 C1 0.2(3) . . . . ?
Cl1B C16B C15B C14B -178.3(10) . . . . ?
C12 C13A C18 S1 4.3(4) . . . . ?
C12 C13A C18 C17A 179.9(4) . . . . ?
C18 S1 N4 C12 6.94(10) . . . . ?
C18 S1 N3 C11 53.17(12) . . . . ?
C18 C17A C16A Cl1A -178.8(6) . . . . ?
C18 C17A C16A C15A -0.2(4) . . . . ?
C18 C13A C12 O1 -179.7(2) . . . . ?
C18 C13A C12 N4 0.3(4) . . . . ?
C18 C17B C16B Cl1B 178.3(10) . . . . ?
C18 C17B C16B C15B 0.0 . . . . ?
C17B C18 C13B C12 -177.1(8) . . . . ?
C17B C18 C13B C14B 0.0 . . . . ?
C17B C16B C15B C14B 0.0 . . . . ?
C16B C15B C14B C13B 0.0 . . . . ?
C16B C15B C14B F1B 177.1(11) . . . . ?
C15B C14B C13B C12 176.8(9) . . . . ?
C15B C14B C13B C18 0.0 . . . . ?
C13B C18 C17B C16B 0.0 . . . . ?
F1B C14B C13B C12 0.1(9) . . . . ?
F1B C14B C13B C18 -176.8(12) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_49
_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 1.692
_oxdiff_exptl_absorpt_empirical_full_min 0.711
####################################################################### 
# 
# 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_az14353142_meoh
_database_code_depnum_ccdc_archive 'CCDC 2517068'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-11-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Cl N5 O2 S, C H4 O'
_chemical_formula_sum            'C20 H16 Cl N5 O3 S'
_chemical_formula_weight         441.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S Cl'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.20830(10)
_cell_length_b                   11.84060(10)
_cell_length_c                   14.43660(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.9080(10)
_cell_angle_gamma                90
_cell_volume                     1962.15(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15190
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.3780
_cell_measurement_theta_min      3.8250
_shelx_estimated_absorpt_T_max   0.767
_shelx_estimated_absorpt_T_min   0.573
_exptl_absorpt_coefficient_mu    3.016
_exptl_absorpt_correction_T_max  0.579
_exptl_absorpt_correction_T_min  0.162
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.0537
0 1 -1 0.0850
-1 5 5 0.1416
0 -1 1 0.1007
-5 -1 0 0.0438
5 1 0 0.0494
-5 2 5 0.1064
5 -2 -5 0.0662
2 -2 -5 0.0662
-2 -3 -5 0.0685
2 -5 -5 0.0550
3 -5 0 0.0814
1 -1 1 0.0953
-1 1 -1 0.0831
-3 5 3 0.1083
-1 3 5 0.1504
-3 -5 5 0.0936
-2 -2 5 0.1117
5 4 -5 0.0744
5 -3 -3 0.0537
-1 0 0 0.0475

_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.093
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0011 -0.9989 -0.9989 -0.0179 0.0486 0.1646
0.0006 0.9993 -0.9990 -0.0198 -0.1697 0.0235
-0.9937 4.9949 4.9942 -0.0424 -0.2554 -0.8021
-0.0006 -0.9993 0.9990 0.0198 0.1697 -0.0235
-4.9967 -0.9974 -0.0007 -0.6585 0.0481 0.1744
4.9967 0.9974 0.0007 0.6585 -0.0481 -0.1744
-4.9930 1.9989 4.9938 -0.5671 0.0232 -0.5074
4.9930 -1.9989 -4.9938 0.5671 -0.0232 0.5074
1.9955 -1.9979 -4.9942 0.1714 -0.0598 0.5698
-2.0021 -2.9957 -4.9948 -0.3552 0.0005 0.7234
1.9928 -4.9952 -4.9940 0.1743 0.2676 0.7814
2.9932 -4.9965 0.0008 0.4006 0.5824 0.2904
0.9985 -0.9996 0.9992 0.1518 0.1819 -0.0443
-0.9985 0.9996 -0.9992 -0.1518 -0.1819 0.0443
-2.9925 4.9959 2.9960 -0.3440 -0.4009 -0.5725
-0.9954 2.9966 4.9943 -0.0405 -0.0371 -0.6611
-3.0007 -4.9955 4.9945 -0.2965 0.8118 -0.0552
-1.9989 -1.9985 4.9945 -0.1675 0.4965 -0.2876
4.9982 3.9958 -4.9942 0.5613 -0.6782 0.0842
4.9926 -2.9984 -2.9958 0.6058 0.2070 0.3899
-0.9992 0.0003 -0.0002 -0.1319 -0.0122 0.0208

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.237
_diffrn_reflns_theta_min         3.851
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     82.00 177.00   0.50    0.07    --  108.39  77.00 -27.00  190
  2  ω     80.00 165.00   0.50    0.07    --   96.59  77.00-120.00  170
  3  ω     31.00 122.00   0.50    0.05    --   50.70  57.00 -90.00  182
  4  ω     24.00 119.00   0.50    0.05    --   50.70  77.00 -27.00  190
  5  ω     31.00 126.00   0.50    0.05    --   50.70  57.00  60.00  190
  6  ω     92.00 178.00   0.50    0.07    --  108.39  45.00  90.00  172
  7  ω     31.00 126.00   0.50    0.05    --   50.70  57.00 150.00  190
  8  ω     95.00 171.00   0.50    0.07    --   96.59 125.00 -90.00  152
  9  ω     95.00 171.00   0.50    0.07    --   96.59 125.00-180.00  152
 10  ω     40.00 105.00   0.50    0.07    --  108.39 -95.00  30.00  130
 11  ω     17.00 118.00   0.50    0.07    --   96.59 -30.00-180.00  202
 12  ω     40.00 135.00   0.50    0.07    --  108.39 -77.00-153.00  190
 13  ω     28.00 123.00   0.50    0.07    --   96.59 -77.00-153.00  190
 14  ω    -18.00  77.00   0.50    0.05    --   50.70 -77.00-153.00  190
 15  ω   -107.00 -11.00   0.50    0.07    --  -79.95  77.00 -27.00  192
 16  ω    -78.00  17.00   0.50    0.05    --  -51.20  77.00 -27.00  190
 17  ω   -120.00 -24.00   0.50    0.05    --  -51.20 -77.00-153.00  192
 18  ω   -148.00 -53.00   0.50    0.07    --  -79.95 -77.00-153.00  190
 19  ω   -149.00 -86.00   0.50    0.07    --  -79.95 -95.00-180.00  126
 20  ω   -148.00 -80.00   0.50    0.07    --  -79.95 -77.00 -90.00  136
 21  ω   -125.00 -76.00   0.50    0.05    --  -51.20-125.00   0.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1320100000
_diffrn_orient_matrix_UB_12      -0.0010929000
_diffrn_orient_matrix_UB_13      0.0188598000
_diffrn_orient_matrix_UB_21      0.0121713000
_diffrn_orient_matrix_UB_22      -0.1092640000
_diffrn_orient_matrix_UB_23      0.0605550000
_diffrn_orient_matrix_UB_31      -0.0207978000
_diffrn_orient_matrix_UB_32      -0.0705847000
_diffrn_orient_matrix_UB_33      -0.0941560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3804
_reflns_number_total             4026
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.390
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.040
_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)+(0.0464P)²+1.4115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0955
_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:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.02589(4) 0.50684(4) 0.85219(3) 0.02754(12) Uani 1 1 d . . . . .
S1 S 0.27783(3) 0.18557(3) 0.88067(3) 0.02145(12) Uani 1 1 d . . . . .
O1 O 0.24339(11) 0.06809(10) 0.86707(9) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.15941(11) 0.38001(10) 1.01632(8) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.40965(12) 0.39188(12) 0.87114(10) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.57921(13) 0.28087(13) 0.91459(10) 0.0236(3) Uani 1 1 d . . . . .
H2 H 0.611(2) 0.213(2) 0.9298(18) 0.045(7) Uiso 1 1 d . . . . .
N3 N 0.40530(13) 0.19123(12) 0.87878(11) 0.0254(3) Uani 1 1 d . . . . .
N4 N 0.26667(12) 0.24192(12) 0.97611(10) 0.0238(3) Uani 1 1 d . . . . .
N5 N -0.01201(13) 0.35672(13) 0.44930(11) 0.0294(3) Uani 1 1 d . . . . .
C1 C 0.29298(16) 0.59641(15) 0.83050(13) 0.0280(4) Uani 1 1 d . . . . .
H1 H 0.251659 0.527847 0.828011 0.034 Uiso 1 1 calc R U . . .
C2 C 0.23219(17) 0.69753(16) 0.80848(14) 0.0312(4) Uani 1 1 d . . . . .
H2A H 0.149714 0.697728 0.790170 0.037 Uiso 1 1 calc R U . . .
C3 C 0.29175(17) 0.79842(15) 0.81317(13) 0.0303(4) Uani 1 1 d . . . . .
H3 H 0.250349 0.867784 0.798096 0.036 Uiso 1 1 calc R U . . .
C4 C 0.41185(18) 0.79717(16) 0.83998(14) 0.0326(4) Uani 1 1 d . . . . .
H4 H 0.452891 0.866257 0.844384 0.039 Uiso 1 1 calc R U . . .
C5 C 0.47318(16) 0.69603(15) 0.86054(13) 0.0294(4) Uani 1 1 d . . . . .
H5 H 0.555509 0.696193 0.877527 0.035 Uiso 1 1 calc R U . . .
C6 C 0.41392(15) 0.59404(14) 0.85625(11) 0.0233(3) Uani 1 1 d . . . . .
C7 C 0.47640(15) 0.48400(14) 0.87650(12) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.59715(15) 0.47576(15) 0.89841(12) 0.0251(3) Uani 1 1 d . . . . .
H8 H 0.642465 0.541086 0.898774 0.030 Uiso 1 1 calc R U . . .
C9 C 0.64884(15) 0.37081(15) 0.91945(12) 0.0244(3) Uani 1 1 d . . . . .
C10 C 0.77619(15) 0.34875(16) 0.94722(13) 0.0283(4) Uani 1 1 d . . . . .
H10A H 0.802621 0.303171 1.007454 0.042 Uiso 1 1 calc R U . . .
H10B H 0.818388 0.420689 0.958694 0.042 Uiso 1 1 calc R U . . .
H10C H 0.791277 0.307876 0.893770 0.042 Uiso 1 1 calc R U . . .
C11 C 0.46158(15) 0.29109(14) 0.88814(12) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.18327(14) 0.32394(14) 0.95430(12) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.12516(14) 0.34091(14) 0.84425(12) 0.0210(3) Uani 1 1 d . . . . .
C14 C 0.03782(14) 0.41531(14) 0.79242(12) 0.0223(3) Uani 1 1 d . . . . .
C15 C 0.00205(14) 0.41866(14) 0.68972(12) 0.0227(3) Uani 1 1 d . . . . .
H15 H -0.057319 0.469584 0.653729 0.027 Uiso 1 1 calc R U . . .
C16 C 0.05429(14) 0.34643(14) 0.64010(12) 0.0218(3) Uani 1 1 d . . . . .
C17 C 0.14185(14) 0.26976(14) 0.69040(12) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.177185 0.220577 0.656826 0.026 Uiso 1 1 calc R U . . .
C18 C 0.17342(14) 0.27021(13) 0.79153(12) 0.0210(3) Uani 1 1 d . . . . .
C19 C 0.01679(14) 0.35235(15) 0.53360(13) 0.0243(3) Uani 1 1 d . . . . .
O3 O 0.69682(13) 0.08377(12) 0.97372(10) 0.0364(3) Uani 1 1 d . . . . .
H3A H 0.698(3) 0.043(3) 1.021(2) 0.070(9) Uiso 1 1 d . . . . .
C20 C 0.7039(2) 0.01340(18) 0.89659(15) 0.0406(5) Uani 1 1 d . . . . .
H20A H 0.628036 0.011344 0.843644 0.061 Uiso 1 1 calc R U . . .
H20B H 0.725827 -0.063167 0.921880 0.061 Uiso 1 1 calc R U . . .
H20C H 0.762708 0.043354 0.870893 0.061 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 C14 1.7266(17) . ?
S1 O1 1.4472(12) . ?
S1 N3 1.5671(15) . ?
S1 N4 1.5781(14) . ?
S1 C18 1.7798(16) . ?
O2 C12 1.227(2) . ?
N1 C7 1.348(2) . ?
N1 C11 1.334(2) . ?
N2 H2 0.88(3) . ?
N2 C9 1.349(2) . ?
N2 C11 1.360(2) . ?
N3 C11 1.351(2) . ?
N4 C12 1.364(2) . ?
N5 C19 1.147(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(3) . ?
C1 C6 1.395(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(2) . ?
C6 C7 1.488(2) . ?
C7 C8 1.402(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(2) . ?
C9 C10 1.491(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.517(2) . ?
C13 C14 1.389(2) . ?
C13 C18 1.390(2) . ?
C14 C15 1.396(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.401(2) . ?
C16 C17 1.402(2) . ?
C16 C19 1.449(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(2) . ?
O3 H3A 0.83(3) . ?
O3 C20 1.417(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O1 S1 N3 106.45(7) . . ?
O1 S1 N4 114.67(7) . . ?
O1 S1 C18 109.86(7) . . ?
N3 S1 N4 112.25(8) . . ?
N3 S1 C18 115.74(8) . . ?
N4 S1 C18 98.03(8) . . ?
C11 N1 C7 118.23(15) . . ?
C9 N2 H2 119.1(16) . . ?
C9 N2 C11 122.05(15) . . ?
C11 N2 H2 118.8(16) . . ?
C11 N3 S1 120.66(12) . . ?
C12 N4 S1 112.27(11) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 120.90(17) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.07(18) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.49(17) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.77(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.12(17) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.63(16) . . ?
C1 C6 C7 119.70(15) . . ?
C5 C6 C7 121.65(16) . . ?
N1 C7 C6 115.97(15) . . ?
N1 C7 C8 121.69(16) . . ?
C8 C7 C6 122.33(15) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.64(16) . . ?
C9 C8 H8 120.7 . . ?
N2 C9 C8 117.81(16) . . ?
N2 C9 C10 117.17(15) . . ?
C8 C9 C10 125.03(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 N2 121.43(16) . . ?
N1 C11 N3 124.80(15) . . ?
N3 C11 N2 113.75(15) . . ?
O2 C12 N4 124.12(15) . . ?
O2 C12 C13 123.39(15) . . ?
N4 C12 C13 112.47(14) . . ?
C14 C13 C12 130.37(15) . . ?
C14 C13 C18 118.54(15) . . ?
C18 C13 C12 111.07(14) . . ?
C13 C14 Cl1 121.51(13) . . ?
C13 C14 C15 119.68(15) . . ?
C15 C14 Cl1 118.79(13) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.57(15) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 122.01(15) . . ?
C15 C16 C19 118.61(15) . . ?
C17 C16 C19 119.38(15) . . ?
C16 C17 H17 122.1 . . ?
C18 C17 C16 115.81(15) . . ?
C18 C17 H17 122.1 . . ?
C13 C18 S1 106.02(12) . . ?
C17 C18 S1 129.59(13) . . ?
C17 C18 C13 124.39(15) . . ?
N5 C19 C16 179.43(19) . . ?
C20 O3 H3A 109(2) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Cl1 C14 C15 C16 178.85(12) . . . . ?
S1 N3 C11 N1 -20.4(2) . . . . ?
S1 N3 C11 N2 161.33(12) . . . . ?
S1 N4 C12 O2 -179.49(13) . . . . ?
S1 N4 C12 C13 -1.18(17) . . . . ?
O1 S1 N3 C11 178.91(13) . . . . ?
O1 S1 N4 C12 -113.50(12) . . . . ?
O1 S1 C18 C13 116.38(12) . . . . ?
O1 S1 C18 C17 -63.14(17) . . . . ?
O2 C12 C13 C14 -1.3(3) . . . . ?
O2 C12 C13 C18 176.73(15) . . . . ?
N1 C7 C8 C9 -3.1(2) . . . . ?
N3 S1 N4 C12 124.86(12) . . . . ?
N3 S1 C18 C13 -123.07(12) . . . . ?
N3 S1 C18 C17 57.42(18) . . . . ?
N4 S1 N3 C11 -54.87(15) . . . . ?
N4 S1 C18 C13 -3.56(12) . . . . ?
N4 S1 C18 C17 176.92(16) . . . . ?
N4 C12 C13 C14 -179.67(16) . . . . ?
N4 C12 C13 C18 -1.59(19) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 N1 -2.0(2) . . . . ?
C1 C6 C7 C8 177.11(16) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -178.13(16) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 179.19(16) . . . . ?
C5 C6 C7 N1 179.25(15) . . . . ?
C5 C6 C7 C8 -1.7(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C7 C8 C9 177.90(15) . . . . ?
C7 N1 C11 N2 2.9(2) . . . . ?
C7 N1 C11 N3 -175.22(16) . . . . ?
C7 C8 C9 N2 2.1(2) . . . . ?
C7 C8 C9 C10 -177.93(16) . . . . ?
C9 N2 C11 N1 -3.9(2) . . . . ?
C9 N2 C11 N3 174.40(14) . . . . ?
C11 N1 C7 C6 179.62(14) . . . . ?
C11 N1 C7 C8 0.5(2) . . . . ?
C11 N2 C9 C8 1.3(2) . . . . ?
C11 N2 C9 C10 -178.70(15) . . . . ?
C12 C13 C14 Cl1 -1.5(2) . . . . ?
C12 C13 C14 C15 176.97(16) . . . . ?
C12 C13 C18 S1 3.21(16) . . . . ?
C12 C13 C18 C17 -177.24(15) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C13 C18 S1 -178.46(12) . . . . ?
C14 C13 C18 C17 1.1(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C14 C15 C16 C19 -179.25(15) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 S1 178.94(13) . . . . ?
C16 C17 C18 C13 -0.5(2) . . . . ?
C18 S1 N3 C11 56.53(16) . . . . ?
C18 S1 N4 C12 2.75(13) . . . . ?
C18 C13 C14 Cl1 -179.43(12) . . . . ?
C18 C13 C14 C15 -1.0(2) . . . . ?
C19 C16 C17 C18 179.31(15) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_265
_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 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_az14264473_100k
_database_code_depnum_ccdc_archive 'CCDC 2517064'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-02-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 Cl N4 O2 S, C H4 O'
_chemical_formula_sum            'C19 H17 Cl N4 O3 S'
_chemical_formula_weight         416.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S Cl'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.64600(10)
_cell_length_b                   11.12230(10)
_cell_length_c                   22.0722(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.4410(10)
_cell_angle_gamma                90
_cell_volume                     1865.20(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16719
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.3800
_cell_measurement_theta_min      4.0210
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    3.117
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -1 0.0174
-5 0 2 0.0816
5 0 -2 0.1055
0 0 1 0.0073
0 0 -1 0.0211
0 -1 5 0.0092
0 2 -5 0.0119
0 -5 -3 0.0339

_exptl_crystal_preparation       
'The material was recrystallized from methanol by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.026
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0005 4.9961 -1.0001 0.0727 -0.6916 0.0155
-4.9976 0.0006 1.9988 0.0137 0.0260 1.0067
4.9976 -0.0006 -1.9988 -0.0137 -0.0260 -1.0067
0.0000 -0.0001 0.9993 -0.0702 -0.0002 0.0027
-0.0000 0.0001 -0.9993 0.0702 0.0002 -0.0027
0.0001 -0.9995 4.9969 -0.3513 0.1376 0.0100
-0.0002 1.9988 -4.9970 0.3518 -0.2759 -0.0064
0.0005 -4.9959 -2.9973 0.2079 0.6922 -0.0264

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24578
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.793
_diffrn_reflns_theta_min         4.031
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00 115.00   0.50    0.65    --   51.03-138.00-120.00  146
  2  ω     38.00 111.00   0.50    0.65    --   51.03-131.00  55.00  146
  3  ω   -125.00 -70.00   0.50    0.65    --  -51.28-131.00  55.00  110
  4  ω   -124.00 -65.00   0.50    0.65    --  -51.28-138.00-120.00  118
  5  ω    -91.00 -16.00   0.50    0.65    --  -51.28 131.00 125.00  150
  6  ω   -154.00 -70.00   0.50    1.73    --  -79.95-131.00  55.00  168
  7  ω   -153.00 -65.00   0.50    1.73    --  -79.95-138.00-120.00  176
  8  ω     42.00 121.00   0.50    1.73    --   96.44-138.00-120.00  158
  9  ω     38.00 116.00   0.50    1.73    --   96.44-131.00  55.00  156
 10  ω     91.00 178.00   0.50    1.73    --  108.37 131.00 125.00  174
 11  ω     87.00 175.00   0.50    1.73    --  108.37 138.00 -59.00  176
 12  ω     16.00  43.00   0.50    0.65    --   44.00  79.00-148.17   54
 13  ω     17.00  43.00   0.50    0.65    --   44.00  78.00 -23.21   52
 14  ω     80.00 120.00   0.50    0.65    --   51.03  77.00 150.00   80
 15  ω   -120.00 -80.00   0.50    0.65    --  -51.28 -77.00 -30.00   80
 16  ω    -90.00 -16.00   0.50    1.73    --  -79.95 131.00 125.00  148
 17  ω   -149.00 -86.00   0.50    1.73    --  -79.95 -95.00 -30.00  126
 18  ω   -159.00 -65.00   0.50    1.73    --  -88.50 -71.00  67.41  188
 19  ω     22.00 117.00   0.50    1.73    --   96.44 -61.00-150.00  190
 20  ω     88.00 178.00   0.50    1.73    --  108.37  30.00  60.00  180
 21  ω     40.00 105.00   0.50    1.73    --  108.37 -95.00  90.00  130
 22  ω     40.00 105.00   0.50    1.73    --  108.37 -95.00  60.00  130
 23  ω     17.00  43.00   0.50    0.65    --   44.00  78.00 -84.20   52
 24  ω     17.00  43.00   0.50    0.65    --   44.00  78.00 132.29   52
 25  ω     17.00  43.00   0.50    0.65    --   44.00  78.00  23.48   52
 26  ω     16.00  43.00   0.50    0.65    --   44.00  79.00 173.91   54
 27  ω     16.00  43.00   0.50    0.65    --   44.00  79.00  65.83   54
 28  ω     80.00 120.00   0.50    0.65    --   51.03  77.00-150.00   80
 29  ω   -158.00 -89.00   0.50    1.73    --  -84.00 -62.00 150.02  138
 30  ω   -162.00 -67.00   0.50    1.73    --  -88.50 -64.00-100.24  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0308156000
_diffrn_orient_matrix_UB_12      0.0004932000
_diffrn_orient_matrix_UB_13      -0.0701964000
_diffrn_orient_matrix_UB_21      -0.0052921000
_diffrn_orient_matrix_UB_22      -0.1384557000
_diffrn_orient_matrix_UB_23      -0.0001679000
_diffrn_orient_matrix_UB_31      -0.2003556000
_diffrn_orient_matrix_UB_32      0.0036185000
_diffrn_orient_matrix_UB_33      0.0027272000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3562
_reflns_number_total             3827
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.332
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.094
_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+1.1563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H17,H3,H3A} of C17
 At 1.5 times of:
  {H10A,H10B,H10C} of C10, {H19A,H19B,H19C} of C19
2. Restrained distances
 N3-H3
 0.88 with sigma of 0.02
 O3-H3A
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.51394(6) 0.51962(4) 0.24318(2) 0.03713(13) Uani 1 1 d . . . . .
S1 S 0.23689(5) 0.83274(3) 0.38189(2) 0.01986(11) Uani 1 1 d . . . . .
O1 O 0.64409(15) 0.69878(12) 0.34665(6) 0.0332(3) Uani 1 1 d . . . . .
O2 O 0.17503(15) 0.95071(10) 0.36181(5) 0.0257(2) Uani 1 1 d . . . . .
N1 N 0.44240(17) 0.81649(12) 0.38806(6) 0.0237(3) Uani 1 1 d . . . . .
N2 N 0.15817(18) 0.80829(12) 0.44362(6) 0.0234(3) Uani 1 1 d . . . . .
N3 N 0.14955(17) 0.70591(12) 0.53233(6) 0.0219(3) Uani 1 1 d D . . . .
N4 N 0.24009(16) 0.60204(11) 0.44836(6) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.4917(2) 0.73074(15) 0.34863(7) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.3366(2) 0.67823(14) 0.30864(7) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.3274(2) 0.59074(15) 0.26360(7) 0.0264(3) Uani 1 1 d . . . . .
C4 C 0.1636(3) 0.55634(16) 0.23458(7) 0.0314(4) Uani 1 1 d . . . . .
H4 H 0.157081 0.496743 0.203582 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0099(2) 0.60815(17) 0.25045(8) 0.0319(4) Uani 1 1 d . . . . .
H5 H -0.100270 0.584156 0.229792 0.038 Uiso 1 1 calc R U . . .
C6 C 0.0147(2) 0.69467(15) 0.29615(7) 0.0265(3) Uani 1 1 d . . . . .
H6 H -0.089539 0.729929 0.307857 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1794(2) 0.72640(14) 0.32352(7) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.18613(19) 0.70301(14) 0.47304(7) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.1720(2) 0.60835(15) 0.56885(7) 0.0236(3) Uani 1 1 d . . . . .
C10 C 0.1384(2) 0.62313(17) 0.63385(7) 0.0320(4) Uani 1 1 d . . . . .
H10A H 0.225527 0.678413 0.654445 0.048 Uiso 1 1 calc R U . . .
H10B H 0.147724 0.544827 0.654318 0.048 Uiso 1 1 calc R U . . .
H10C H 0.019993 0.655840 0.635409 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2261(2) 0.50307(15) 0.54445(7) 0.0252(3) Uani 1 1 d . . . . .
H11 H 0.241212 0.432216 0.568504 0.030 Uiso 1 1 calc R U . . .
C12 C 0.25865(19) 0.50252(14) 0.48296(7) 0.0214(3) Uani 1 1 d . . . . .
C13 C 0.31364(19) 0.39233(14) 0.45265(7) 0.0215(3) Uani 1 1 d . . . . .
C14 C 0.3437(2) 0.28464(15) 0.48445(7) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.328993 0.280967 0.526588 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3948(2) 0.18290(15) 0.45472(8) 0.0310(4) Uani 1 1 d . . . . .
H15 H 0.416705 0.110201 0.476868 0.037 Uiso 1 1 calc R U . . .
C16 C 0.4145(2) 0.18593(15) 0.39325(8) 0.0284(3) Uani 1 1 d . . . . .
H16 H 0.448158 0.115509 0.373143 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3847(3) 0.29234(16) 0.36119(8) 0.0329(4) Uani 1 1 d . . . . .
H17 H 0.397953 0.295008 0.318929 0.039 Uiso 1 1 calc R U . . .
H3 H 0.115(3) 0.7756(16) 0.5477(10) 0.039 Uiso 1 1 d D U . . .
H3A H -0.015(2) 0.949(2) 0.5941(10) 0.039 Uiso 1 1 d D U . . .
C18 C 0.3356(3) 0.39479(16) 0.39056(8) 0.0322(4) Uani 1 1 d . . . . .
H18 H 0.316501 0.467643 0.368330 0.039 Uiso 1 1 calc R U . . .
O3 O 0.07595(16) 0.91795(11) 0.58262(5) 0.0293(3) Uani 1 1 d D . . . .
C19 C 0.1906(2) 1.01097(16) 0.56661(9) 0.0316(4) Uani 1 1 d . . . . .
H19A H 0.128664 1.061580 0.534768 0.047 Uiso 1 1 calc R U . . .
H19B H 0.294384 0.975115 0.551428 0.047 Uiso 1 1 calc R U . . .
H19C H 0.227595 1.060139 0.602617 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
Cl1 C3 1.7345(17) . ?
S1 O2 1.4473(11) . ?
S1 N1 1.5723(13) . ?
S1 N2 1.5738(13) . ?
S1 C7 1.7677(15) . ?
O1 C1 1.2236(19) . ?
N1 C1 1.372(2) . ?
N2 C8 1.344(2) . ?
N3 C8 1.3690(19) . ?
N3 C9 1.351(2) . ?
N3 H3 0.897(16) . ?
N4 C8 1.334(2) . ?
N4 C12 1.343(2) . ?
C1 C2 1.514(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.389(2) . ?
C3 C4 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.380(2) . ?
C9 C10 1.495(2) . ?
C9 C11 1.372(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.407(2) . ?
C12 C13 1.480(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.399(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(2) . ?
C18 H18 0.9500 . ?
O3 H3A 0.840(16) . ?
O3 C19 1.426(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 N1 114.82(7) . . ?
O2 S1 N2 106.15(7) . . ?
O2 S1 C7 109.71(7) . . ?
N1 S1 N2 112.38(7) . . ?
N1 S1 C7 98.67(7) . . ?
N2 S1 C7 115.30(7) . . ?
C1 N1 S1 111.59(11) . . ?
C8 N2 S1 120.87(11) . . ?
C8 N3 H3 118.7(14) . . ?
C9 N3 C8 121.70(14) . . ?
C9 N3 H3 119.5(14) . . ?
C8 N4 C12 118.64(13) . . ?
O1 C1 N1 123.71(15) . . ?
O1 C1 C2 123.63(15) . . ?
N1 C1 C2 112.64(13) . . ?
C3 C2 C1 131.46(15) . . ?
C3 C2 C7 117.66(15) . . ?
C7 C2 C1 110.82(13) . . ?
C2 C3 Cl1 121.93(13) . . ?
C2 C3 C4 119.51(15) . . ?
C4 C3 Cl1 118.55(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.80(15) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.02(16) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 121.9 . . ?
C7 C6 C5 116.30(16) . . ?
C7 C6 H6 121.9 . . ?
C2 C7 S1 106.23(11) . . ?
C6 C7 S1 129.08(13) . . ?
C6 C7 C2 124.69(15) . . ?
N2 C8 N3 113.75(13) . . ?
N4 C8 N2 125.16(13) . . ?
N4 C8 N3 121.07(14) . . ?
N3 C9 C10 117.41(14) . . ?
N3 C9 C11 118.36(14) . . ?
C11 C9 C10 124.23(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11 120.8 . . ?
C9 C11 C12 118.43(14) . . ?
C12 C11 H11 120.8 . . ?
N4 C12 C11 121.74(14) . . ?
N4 C12 C13 116.27(13) . . ?
C11 C12 C13 121.99(14) . . ?
C14 C13 C12 121.53(14) . . ?
C14 C13 C18 118.61(15) . . ?
C18 C13 C12 119.86(14) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.13(15) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.82(16) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.52(16) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.14(16) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.75(16) . . ?
C17 C18 H18 119.6 . . ?
C19 O3 H3A 108.9(16) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Cl1 C3 C4 C5 178.23(13) . . . . ?
S1 N1 C1 O1 -177.01(13) . . . . ?
S1 N1 C1 C2 1.90(16) . . . . ?
S1 N2 C8 N3 164.20(11) . . . . ?
S1 N2 C8 N4 -17.4(2) . . . . ?
O1 C1 C2 C3 -0.8(3) . . . . ?
O1 C1 C2 C7 176.31(15) . . . . ?
O2 S1 N1 C1 -117.15(11) . . . . ?
O2 S1 N2 C8 177.42(12) . . . . ?
O2 S1 C7 C2 119.49(11) . . . . ?
O2 S1 C7 C6 -59.98(16) . . . . ?
N1 S1 N2 C8 -56.29(14) . . . . ?
N1 S1 C7 C2 -0.89(12) . . . . ?
N1 S1 C7 C6 179.64(15) . . . . ?
N1 C1 C2 C3 -179.75(16) . . . . ?
N1 C1 C2 C7 -2.60(18) . . . . ?
N2 S1 N1 C1 121.40(11) . . . . ?
N2 S1 C7 C2 -120.76(11) . . . . ?
N2 S1 C7 C6 59.77(17) . . . . ?
N3 C9 C11 C12 1.2(2) . . . . ?
N4 C12 C13 C14 177.55(14) . . . . ?
N4 C12 C13 C18 -2.8(2) . . . . ?
C1 C2 C3 Cl1 -0.4(2) . . . . ?
C1 C2 C3 C4 178.12(15) . . . . ?
C1 C2 C7 S1 1.98(15) . . . . ?
C1 C2 C7 C6 -178.52(14) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C2 C7 S1 179.57(12) . . . . ?
C3 C2 C7 C6 -0.9(2) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 1.0(2) . . . . ?
C5 C6 C7 S1 179.27(13) . . . . ?
C5 C6 C7 C2 -0.1(2) . . . . ?
C7 S1 N1 C1 -0.63(12) . . . . ?
C7 S1 N2 C8 55.73(15) . . . . ?
C7 C2 C3 Cl1 -177.39(11) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C8 N3 C9 C10 176.44(14) . . . . ?
C8 N3 C9 C11 -2.7(2) . . . . ?
C8 N4 C12 C11 -1.3(2) . . . . ?
C8 N4 C12 C13 178.21(13) . . . . ?
C9 N3 C8 N2 -179.29(14) . . . . ?
C9 N3 C8 N4 2.2(2) . . . . ?
C9 C11 C12 N4 0.8(2) . . . . ?
C9 C11 C12 C13 -178.65(14) . . . . ?
C10 C9 C11 C12 -177.88(15) . . . . ?
C11 C12 C13 C14 -3.0(2) . . . . ?
C11 C12 C13 C18 176.66(15) . . . . ?
C12 N4 C8 N2 -178.49(14) . . . . ?
C12 N4 C8 N3 -0.2(2) . . . . ?
C12 C13 C14 C15 179.91(15) . . . . ?
C12 C13 C18 C17 -179.15(16) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C13 C18 C17 0.5(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 -0.6(3) . . . . ?
C18 C13 C14 C15 0.3(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_301
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.651
####################################################################### 
# 
# 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_az14336522_100k
_database_code_depnum_ccdc_archive 'CCDC 2517066'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-07-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 F N5 O2 S, 1.5(C2 H6 O S)'
_chemical_formula_sum            'C22 H21 F N5 O3.50 S2.50'
_chemical_formula_weight         510.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S F'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.83493(5)
_cell_length_b                   33.96028(12)
_cell_length_c                   24.05716(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.8194(4)
_cell_angle_gamma                90
_cell_volume                     9389.11(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    125852
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.3830
_cell_measurement_theta_min      3.2030
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.660
_exptl_absorpt_coefficient_mu    2.870
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 1 0.0774
2 5 -2 0.0694
0 -1 -2 0.0723
0 1 2 0.0504
2 -5 -2 0.0203
-3 2 -1 0.0424
-2 5 0 0.0284
-1 -2 3 0.0750
0 0 0 0.0794
1 5 -2 0.0739

_exptl_crystal_preparation       
'The material was recrystallized from DMSO by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow evaporation'
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0008 -5.0013 0.9999 -0.0481 -0.2205 0.1367
2.0007 5.0017 -2.0002 -0.0429 0.3193 -0.1419
-0.0005 -0.9990 -2.4995 0.0087 0.0726 0.1546
0.0005 0.9990 2.4995 -0.0087 -0.0726 -0.1546
1.9991 -5.0004 -1.5010 -0.3286 0.0568 0.0956
-3.0000 2.0011 -0.9981 0.3873 -0.0930 0.1680
-1.9993 5.0013 -0.4985 0.3578 0.0207 0.0070
-1.0000 -2.0017 2.9997 0.0061 -0.2250 -0.0448
-0.0001 0.0002 -0.4999 0.0073 0.0194 0.0257
1.0006 5.0020 -2.4996 0.0701 0.2786 -0.0598

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            240833
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.610
_diffrn_reflns_theta_min         3.218
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  69.00   0.50    0.73    --   50.95 -52.00 176.00  190
  2  ω   -128.00 -33.00   0.50    0.73    --  -51.38 -52.00 176.00  190
  3  ω    -70.00  25.00   0.50    0.73    --  -51.38  52.00 -37.00  190
  4  ω   -157.00 -61.00   0.50    1.67    --  -79.95 -52.00 176.00  192
  5  ω    -98.00  -3.00   0.50    1.67    --  -79.95  52.00 -37.00  190
  6  ω     90.00 178.00   0.50    1.67    --  108.39  52.00 -37.00  176
  7  ω     32.00 127.00   0.50    1.67    --  108.39 -52.00 176.00  190
  8  ω     11.00  38.00   0.50    0.73    --   40.00  82.00  37.03   54
  9  ω   -149.00 -86.00   0.50    1.67    --  -79.95 -95.00 -30.00  126
 10  ω    -86.00 -13.00   0.50    1.67    --  -79.95 125.00-180.00  146
 11  ω   -100.00  -5.00   0.50    1.67    --  -79.95  61.00-150.00  190
 12  ω   -149.00 -86.00   0.50    1.67    --  -79.95 -95.00 -90.00  126
 13  ω     80.00 175.00   0.50    1.67    --   96.59  45.00 -90.00  190
 14  ω     95.00 171.00   0.50    1.67    --   96.59 125.00-150.00  152
 15  ω     20.00 115.00   0.50    1.67    --   96.59 -52.00 176.00  190
 16  ω     28.00 105.00   0.50    1.67    --   96.59 -95.00-180.00  154
 17  ω     28.00 105.00   0.50    1.67    --   96.59 -95.00 -90.00  154
 18  ω     95.00 171.00   0.50    1.67    --   96.59 125.00 150.00  152
 19  ω     78.00 173.00   0.50    1.67    --   96.59  52.00 -37.00  190
 20  ω     30.00 108.00   0.50    1.67    --  102.49-106.00  33.79  156
 21  ω     40.00 105.00   0.50    1.67    --  108.39 -95.00 -30.00  130
 22  ω     40.00 105.00   0.50    1.67    --  108.39 -95.00  60.00  130
 23  ω     29.00 129.00   0.50    1.67    --  108.39 -30.00 -60.00  200
 24  ω     34.00 112.00   0.50    1.67    --  108.39-125.00-180.00  156
 25  ω     40.00 105.00   0.50    1.67    --  108.39 -95.00-150.00  130
 26  ω     11.00  38.00   0.50    0.73    --   40.00  82.00 -23.76   54
 27  ω     17.00  43.00   0.50    0.73    --   44.00  78.00 -76.55   52
 28  ω     16.00  43.00   0.50    0.73    --   44.00  79.00 138.73   54
 29  ω     40.00 135.00   0.50    0.73    --   64.00  72.00  54.91  190
 30  ω   -145.00 -51.00   0.50    1.67    --  -72.00 -64.00 -26.07  188
 31  ω   -144.00 -49.00   0.50    1.67    --  -72.00 -68.00-101.88  190
 32  ω   -144.00 -49.00   0.50    1.67    --  -72.00 -69.00 167.52  190
 33  ω   -151.00 -56.00   0.50    1.67    --  -80.00 -71.00 125.78  190
 34  ω   -151.00 -56.00   0.50    1.67    --  -80.00 -71.00 -30.46  190
 35  ω   -157.00 -62.00   0.50    1.67    --  -84.00 -66.00  12.79  190
 36  ω   -160.00 -65.00   0.50    1.67    --  -88.00 -68.00-124.78  190
 37  ω   -160.00 -66.00   0.50    1.67    --  -88.50 -69.00 114.30  188
 38  ω   -160.00 -66.00   0.50    1.67    --  -88.50 -69.00  45.49  188
 39  ω   -160.00 -65.00   0.50    1.67    --  -88.50 -70.00 170.08  190
 40  ω   -161.00 -66.00   0.50    1.67    --  -88.50 -67.00  78.07  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1056676000
_diffrn_orient_matrix_UB_12      0.0278468000
_diffrn_orient_matrix_UB_13      -0.0145976000
_diffrn_orient_matrix_UB_21      0.0601050000
_diffrn_orient_matrix_UB_22      0.0243015000
_diffrn_orient_matrix_UB_23      -0.0387630000
_diffrn_orient_matrix_UB_31      -0.0564766000
_diffrn_orient_matrix_UB_32      -0.0263009000
_diffrn_orient_matrix_UB_33      -0.0513210000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                18366
_reflns_number_total             19709
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.647
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1272
_refine_ls_number_reflns         19709
_refine_ls_number_restraints     1003
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+6.4971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          
'DMSO molecule containing S9, O13, C88 and C87 is refined to have disorder with occupancy approximately 0.82: 0.18'
_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. Restrained distances
 S9A-O13A \\sim S9B-O13B
 with sigma of 0.02
 S9A-C87A \\sim S9B-C87B
 with sigma of 0.02
 S9A-C88A \\sim S9B-C88B
 with sigma of 0.02
 C87A-C88A \\sim C87B-C88B
 with sigma of 0.04
 O13A-C88A \\sim O13B-C88B
 with sigma of 0.04
 O13A-C87A \\sim O13B-C87B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C88A) = Uanis(C87B)
Uanis(C88B) = Uanis(C87A)
Uanis(O13B) = Uanis(O13A)
Uanis(S9A) = Uanis(S9B)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S9B)=Sof(O13B)=Sof(C87B)=Sof(H87D)=Sof(H87E)=Sof(H87F)=Sof(C88B)=
 Sof(H88D)=Sof(H88E)=Sof(H88F)=1-FVAR(1)
 Sof(S9A)=Sof(O13A)=Sof(C87A)=Sof(H87A)=Sof(H87B)=Sof(H87C)=Sof(C88A)=
 Sof(H88A)=Sof(H88B)=Sof(H88C)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C17(H17), C20(H20),
  C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C34(H34), C36(H36),
 C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46), C53(H53), C55(H55),
  C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C65(H65), C72(H72), C74(H74)
6.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C29(H29A,H29B,H29C), C48(H48A,H48B,H48C), C67(H67A,H67B,
 H67C), C77(H77A,H77B,H77C), C78(H78A,H78B,H78C), C79(H79A,H79B,H79C), C80(H80A,
 H80B,H80C), C81(H81A,H81B,H81C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C),
 C84(H84A,H84B,H84C), C87A(H87A,H87B,H87C), C88A(H88A,H88B,H88C), C87B(H87D,
 H87E,H87F), C88B(H88D,H88E,H88F), C85(H85A,H85B,H85C), C86(H86A,H86B,H86C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.67324(3) 0.88237(2) 0.57496(2) 0.02049(8) Uani 1 1 d . . . . .
F1 F 0.78649(9) 0.90072(3) 0.39375(4) 0.0338(2) Uani 1 1 d . . . . .
O1 O 0.72362(10) 0.85114(3) 0.61340(5) 0.0297(3) Uani 1 1 d . . . . .
O2 O 0.84540(9) 0.94354(3) 0.50225(5) 0.0269(2) Uani 1 1 d . . . . .
N1 N 0.43237(10) 0.94653(4) 0.59668(5) 0.0177(2) Uani 1 1 d . . . . .
H1 H 0.4460(18) 0.9418(6) 0.6350(10) 0.039(6) Uiso 1 1 d . . . . .
N2 N 0.48240(10) 0.93276(4) 0.50980(5) 0.0182(2) Uani 1 1 d . . . . .
N3 N 0.56582(11) 0.89838(4) 0.59537(5) 0.0225(3) Uani 1 1 d . . . . .
N4 N 0.75897(11) 0.91711(4) 0.56941(5) 0.0225(3) Uani 1 1 d . . . . .
N5 N 0.45409(15) 0.77464(5) 0.35514(9) 0.0489(5) Uani 1 1 d . . . . .
C1 C 0.44558(13) 0.93800(5) 0.39253(7) 0.0244(3) Uani 1 1 d . . . . .
H1A H 0.494520 0.918109 0.413257 0.029 Uiso 1 1 calc R U . . .
C2 C 0.43237(15) 0.94111(5) 0.33379(7) 0.0283(3) Uani 1 1 d . . . . .
H2 H 0.472181 0.923455 0.314453 0.034 Uiso 1 1 calc R U . . .
C3 C 0.36069(15) 0.97014(5) 0.30340(7) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.351266 0.972300 0.263181 0.034 Uiso 1 1 calc R U . . .
C4 C 0.30296(15) 0.99592(5) 0.33163(7) 0.0273(3) Uani 1 1 d . . . . .
H4 H 0.254244 1.015784 0.310678 0.033 Uiso 1 1 calc R U . . .
C5 C 0.31585(14) 0.99293(4) 0.39052(6) 0.0229(3) Uani 1 1 d . . . . .
H5 H 0.275861 1.010672 0.409643 0.027 Uiso 1 1 calc R U . . .
C6 C 0.38768(12) 0.96381(4) 0.42151(6) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.40170(12) 0.95906(4) 0.48400(6) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.33373(12) 0.98000(4) 0.51429(6) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.276756 0.998327 0.495376 0.023 Uiso 1 1 calc R U . . .
C9 C 0.35173(12) 0.97330(4) 0.57221(6) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.28635(14) 0.99374(5) 0.60955(7) 0.0246(3) Uani 1 1 d . . . . .
H10A H 0.222617 0.976858 0.614882 0.037 Uiso 1 1 calc R U . . .
H10B H 0.254478 1.018513 0.591500 0.037 Uiso 1 1 calc R U . . .
H10C H 0.338960 0.999290 0.646815 0.037 Uiso 1 1 calc R U . . .
C11 C 0.49525(12) 0.92617(4) 0.56560(6) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.78243(12) 0.91883(4) 0.51696(7) 0.0208(3) Uani 1 1 d . . . . .
C13 C 0.71833(12) 0.88747(4) 0.47698(6) 0.0208(3) Uani 1 1 d . . . . .
C14 C 0.64698(13) 0.86496(4) 0.50250(7) 0.0215(3) Uani 1 1 d . . . . .
C15 C 0.57602(13) 0.83517(5) 0.47458(7) 0.0261(3) Uani 1 1 d . . . . .
H15 H 0.528144 0.820036 0.493038 0.031 Uiso 1 1 calc R U . . .
C16 C 0.57893(14) 0.82861(5) 0.41732(8) 0.0285(3) Uani 1 1 d . . . . .
C17 C 0.64937(14) 0.85062(5) 0.38992(7) 0.0291(3) Uani 1 1 d . . . . .
H17 H 0.649475 0.845699 0.351062 0.035 Uiso 1 1 calc R U . . .
C18 C 0.71882(13) 0.87970(5) 0.42060(7) 0.0249(3) Uani 1 1 d . . . . .
C19 C 0.50804(15) 0.79831(6) 0.38376(9) 0.0362(4) Uani 1 1 d . . . . .
S2 S 1.15427(3) 0.87050(2) 0.56004(2) 0.02062(8) Uani 1 1 d . . . . .
F2 F 1.28503(8) 0.84768(3) 0.38438(4) 0.0298(2) Uani 1 1 d . . . . .
O3 O 1.20558(10) 0.90226(3) 0.59712(5) 0.0295(2) Uani 1 1 d . . . . .
O4 O 1.33188(9) 0.80607(3) 0.49459(5) 0.0266(2) Uani 1 1 d . . . . .
N6 N 0.96607(10) 0.81975(3) 0.49552(5) 0.0179(2) Uani 1 1 d . . . . .
N7 N 0.91746(10) 0.80614(4) 0.58279(5) 0.0186(2) Uani 1 1 d . . . . .
H7 H 0.9327(19) 0.8113(7) 0.6216(10) 0.044(6) Uiso 1 1 d . . . . .
N8 N 1.04390(11) 0.85651(4) 0.57950(5) 0.0219(3) Uani 1 1 d . . . . .
N9 N 1.23747(11) 0.83426(4) 0.55758(6) 0.0236(3) Uani 1 1 d . . . . .
N10 N 0.93980(15) 0.97084(5) 0.33442(8) 0.0437(4) Uani 1 1 d . . . . .
C20 C 0.94006(13) 0.81068(5) 0.37953(7) 0.0237(3) Uani 1 1 d . . . . .
H20 H 0.989658 0.830445 0.400188 0.028 Uiso 1 1 calc R U . . .
C21 C 0.92936(14) 0.80674(5) 0.32115(7) 0.0263(3) Uani 1 1 d . . . . .
H21 H 0.971647 0.823651 0.302003 0.032 Uiso 1 1 calc R U . . .
C22 C 0.85661(15) 0.77800(5) 0.29076(7) 0.0272(3) Uani 1 1 d . . . . .
H22 H 0.849251 0.775144 0.250767 0.033 Uiso 1 1 calc R U . . .
C23 C 0.79463(15) 0.75342(5) 0.31886(7) 0.0273(3) Uani 1 1 d . . . . .
H23 H 0.744464 0.733915 0.297906 0.033 Uiso 1 1 calc R U . . .
C24 C 0.80548(14) 0.75717(4) 0.37739(6) 0.0230(3) Uani 1 1 d . . . . .
H24 H 0.763108 0.740184 0.396379 0.028 Uiso 1 1 calc R U . . .
C25 C 0.87885(12) 0.78597(4) 0.40835(6) 0.0178(3) Uani 1 1 d . . . . .
C26 C 0.89079(12) 0.79149(4) 0.47060(6) 0.0174(3) Uani 1 1 d . . . . .
C27 C 0.82722(12) 0.76947(4) 0.50179(6) 0.0194(3) Uani 1 1 d . . . . .
H27 H 0.774299 0.749703 0.483683 0.023 Uiso 1 1 calc R U . . .
C28 C 0.84317(12) 0.77714(4) 0.55930(6) 0.0195(3) Uani 1 1 d . . . . .
C29 C 0.78256(15) 0.75547(5) 0.59762(7) 0.0268(3) Uani 1 1 d . . . . .
H29A H 0.838825 0.748440 0.633195 0.040 Uiso 1 1 calc R U . . .
H29B H 0.747241 0.731463 0.578425 0.040 Uiso 1 1 calc R U . . .
H29C H 0.721781 0.772252 0.606445 0.040 Uiso 1 1 calc R U . . .
C30 C 0.97685(12) 0.82716(4) 0.55097(6) 0.0183(3) Uani 1 1 d . . . . .
C31 C 1.26760(12) 0.83146(4) 0.50641(6) 0.0208(3) Uani 1 1 d . . . . .
C32 C 1.20865(12) 0.86247(4) 0.46444(6) 0.0198(3) Uani 1 1 d . . . . .
C33 C 1.21393(13) 0.86929(4) 0.40846(7) 0.0218(3) Uani 1 1 d . . . . .
C34 C 1.14568(13) 0.89774(5) 0.37541(7) 0.0243(3) Uani 1 1 d . . . . .
H34 H 1.149098 0.901897 0.336791 0.029 Uiso 1 1 calc R U . . .
C35 C 1.07138(13) 0.92030(4) 0.40008(7) 0.0241(3) Uani 1 1 d . . . . .
C36 C 1.06504(13) 0.91522(4) 0.45721(7) 0.0223(3) Uani 1 1 d . . . . .
H36 H 1.015950 0.930946 0.474162 0.027 Uiso 1 1 calc R U . . .
C37 C 1.13454(12) 0.88597(4) 0.48706(6) 0.0197(3) Uani 1 1 d . . . . .
C38 C 0.99806(15) 0.94892(5) 0.36430(8) 0.0309(4) Uani 1 1 d . . . . .
S3 S 0.32772(3) 0.62250(2) 0.41989(2) 0.02033(8) Uani 1 1 d . . . . .
F3 F 0.22839(10) 0.60517(3) 0.60402(5) 0.0398(2) Uani 1 1 d . . . . .
O5 O 0.27070(10) 0.65190(3) 0.37984(5) 0.0295(3) Uani 1 1 d . . . . .
O6 O 0.17658(10) 0.55820(3) 0.49911(5) 0.0306(3) Uani 1 1 d . . . . .
N11 N 0.51536(10) 0.57288(3) 0.48560(5) 0.0180(2) Uani 1 1 d . . . . .
N12 N 0.56805(10) 0.55902(4) 0.39931(5) 0.0188(2) Uani 1 1 d . . . . .
H12 H 0.5548(17) 0.5642(6) 0.3613(9) 0.034(5) Uiso 1 1 d . . . . .
N13 N 0.43847(11) 0.60863(4) 0.40044(5) 0.0224(3) Uani 1 1 d . . . . .
N14 N 0.25025(11) 0.58600(4) 0.42821(6) 0.0239(3) Uani 1 1 d . . . . .
N15 N 0.52404(15) 0.74184(5) 0.62595(9) 0.0497(4) Uani 1 1 d . . . . .
C39 C 0.54195(13) 0.56524(5) 0.60219(7) 0.0234(3) Uani 1 1 d . . . . .
H39 H 0.505235 0.587953 0.582921 0.028 Uiso 1 1 calc R U . . .
C40 C 0.54221(14) 0.55920(5) 0.65937(7) 0.0272(3) Uani 1 1 d . . . . .
H40 H 0.506129 0.577797 0.679074 0.033 Uiso 1 1 calc R U . . .
C41 C 0.59543(15) 0.52586(5) 0.68771(7) 0.0299(3) Uani 1 1 d . . . . .
H41 H 0.593866 0.521266 0.726470 0.036 Uiso 1 1 calc R U . . .
C42 C 0.65065(15) 0.49941(5) 0.65920(7) 0.0305(4) Uani 1 1 d . . . . .
H42 H 0.688263 0.476944 0.678814 0.037 Uiso 1 1 calc R U . . .
C43 C 0.65155(13) 0.50544(5) 0.60223(7) 0.0243(3) Uani 1 1 d . . . . .
H43 H 0.690459 0.487289 0.583188 0.029 Uiso 1 1 calc R U . . .
C44 C 0.59522(12) 0.53820(4) 0.57280(6) 0.0191(3) Uani 1 1 d . . . . .
C45 C 0.58872(12) 0.54440(4) 0.51113(6) 0.0179(3) Uani 1 1 d . . . . .
C46 C 0.65376(12) 0.52222(4) 0.48090(6) 0.0201(3) Uani 1 1 d . . . . .
H46 H 0.705531 0.502305 0.499539 0.024 Uiso 1 1 calc R U . . .
C47 C 0.64109(12) 0.52988(4) 0.42352(6) 0.0196(3) Uani 1 1 d . . . . .
C48 C 0.70347(14) 0.50818(5) 0.38603(7) 0.0254(3) Uani 1 1 d . . . . .
H48A H 0.648694 0.501584 0.349799 0.038 Uiso 1 1 calc R U . . .
H48B H 0.736891 0.483932 0.405208 0.038 Uiso 1 1 calc R U . . .
H48C H 0.765875 0.524764 0.378429 0.038 Uiso 1 1 calc R U . . .
C49 C 0.50640(12) 0.57998(4) 0.43011(6) 0.0182(3) Uani 1 1 d . . . . .
C50 C 0.23119(12) 0.58424(4) 0.48197(7) 0.0224(3) Uani 1 1 d . . . . .
C51 C 0.28790(12) 0.61817(4) 0.51884(6) 0.0214(3) Uani 1 1 d . . . . .
C52 C 0.28753(14) 0.62754(5) 0.57462(7) 0.0276(3) Uani 1 1 d . . . . .
C53 C 0.34840(15) 0.65962(5) 0.60148(7) 0.0314(4) Uani 1 1 d . . . . .
H53 H 0.347432 0.665924 0.639840 0.038 Uiso 1 1 calc R U . . .
C54 C 0.41136(14) 0.68267(5) 0.57157(7) 0.0286(3) Uani 1 1 d . . . . .
C55 C 0.41457(13) 0.67434(5) 0.51480(7) 0.0253(3) Uani 1 1 d . . . . .
H55 H 0.457455 0.690025 0.494364 0.030 Uiso 1 1 calc R U . . .
C56 C 0.35151(12) 0.64194(4) 0.49065(6) 0.0203(3) Uani 1 1 d . . . . .
C57 C 0.47453(16) 0.71589(6) 0.60096(9) 0.0374(4) Uani 1 1 d . . . . .
S4 S 0.81079(3) 0.63265(2) 0.40255(2) 0.01767(7) Uani 1 1 d . . . . .
F4 F 0.72642(9) 0.63996(3) 0.59143(4) 0.0346(2) Uani 1 1 d . . . . .
O7 O 0.75610(9) 0.60425(3) 0.36008(4) 0.0241(2) Uani 1 1 d . . . . .
O8 O 0.65835(9) 0.68987(3) 0.48938(5) 0.0276(2) Uani 1 1 d . . . . .
N16 N 1.05476(10) 0.69763(4) 0.38754(5) 0.0180(2) Uani 1 1 d . . . . .
H16 H 1.0431(17) 0.6939(6) 0.3513(9) 0.031(5) Uiso 1 1 d . . . . .
N17 N 0.99844(10) 0.68093(3) 0.47192(5) 0.0176(2) Uani 1 1 d . . . . .
N18 N 0.91843(11) 0.64961(4) 0.38311(5) 0.0205(2) Uani 1 1 d . . . . .
N19 N 0.72883(11) 0.66675(4) 0.41455(5) 0.0212(3) Uani 1 1 d . . . . .
N20 N 1.02114(14) 0.50451(5) 0.59425(9) 0.0511(5) Uani 1 1 d . . . . .
C58 C 1.03632(13) 0.68087(5) 0.59018(6) 0.0234(3) Uani 1 1 d . . . . .
H58 H 1.001583 0.658476 0.569214 0.028 Uiso 1 1 calc R U . . .
C59 C 1.03894(15) 0.68393(5) 0.64796(7) 0.0293(3) Uani 1 1 d . . . . .
H59 H 1.006388 0.663633 0.666424 0.035 Uiso 1 1 calc R U . . .
C60 C 1.08919(15) 0.71669(5) 0.67890(7) 0.0313(4) Uani 1 1 d . . . . .
H60 H 1.089597 0.719069 0.718295 0.038 Uiso 1 1 calc R U . . .
C61 C 1.13864(15) 0.74583(5) 0.65209(7) 0.0293(3) Uani 1 1 d . . . . .
H61 H 1.173632 0.768066 0.673369 0.035 Uiso 1 1 calc R U . . .
C62 C 1.13753(13) 0.74285(4) 0.59435(6) 0.0223(3) Uani 1 1 d . . . . .
H62 H 1.172820 0.762765 0.576476 0.027 Uiso 1 1 calc R U . . .
C63 C 1.08432(12) 0.71043(4) 0.56249(6) 0.0184(3) Uani 1 1 d . . . . .
C64 C 1.07698(12) 0.70701(4) 0.50041(6) 0.0168(3) Uani 1 1 d . . . . .
C65 C 1.14723(12) 0.72914(4) 0.47276(6) 0.0191(3) Uani 1 1 d . . . . .
H65 H 1.202668 0.747272 0.493523 0.023 Uiso 1 1 calc R U . . .
C66 C 1.13403(12) 0.72399(4) 0.41478(6) 0.0183(3) Uani 1 1 d . . . . .
C67 C 1.20287(14) 0.74544(5) 0.38008(7) 0.0246(3) Uani 1 1 d . . . . .
H67A H 1.238991 0.768699 0.401173 0.037 Uiso 1 1 calc R U . . .
H67B H 1.151371 0.753688 0.343716 0.037 Uiso 1 1 calc R U . . .
H67C H 1.263579 0.728061 0.372498 0.037 Uiso 1 1 calc R U . . .
C68 C 0.98919(12) 0.67616(4) 0.41596(6) 0.0174(3) Uani 1 1 d . . . . .
C69 C 0.71425(12) 0.66585(4) 0.46905(7) 0.0205(3) Uani 1 1 d . . . . .
C70 C 0.77851(12) 0.63174(4) 0.50304(6) 0.0187(3) Uani 1 1 d . . . . .
C71 C 0.78466(13) 0.62010(5) 0.55873(7) 0.0240(3) Uani 1 1 d . . . . .
C72 C 0.85109(14) 0.58797(5) 0.58222(7) 0.0270(3) Uani 1 1 d . . . . .
H72 H 0.854929 0.580170 0.620548 0.032 Uiso 1 1 calc R U . . .
C73 C 0.91236(13) 0.56717(5) 0.54881(7) 0.0258(3) Uani 1 1 d . . . . .
C74 C 0.90975(12) 0.57805(4) 0.49236(7) 0.0221(3) Uani 1 1 d . . . . .
H74 H 0.952057 0.564075 0.469731 0.026 Uiso 1 1 calc R U . . .
C75 C 0.84175(12) 0.61039(4) 0.47165(6) 0.0182(3) Uani 1 1 d . . . . .
C76 C 0.97558(15) 0.53250(5) 0.57349(8) 0.0353(4) Uani 1 1 d . . . . .
S5 S 0.41600(3) 0.66873(2) 0.23837(2) 0.02040(8) Uani 1 1 d . . . . .
O9 O 0.46711(10) 0.69249(4) 0.19706(5) 0.0276(2) Uani 1 1 d . . . . .
C77 C 0.51369(14) 0.67594(5) 0.30630(7) 0.0270(3) Uani 1 1 d . . . . .
H77A H 0.589719 0.664684 0.305857 0.040 Uiso 1 1 calc R U . . .
H77B H 0.482935 0.662914 0.335933 0.040 Uiso 1 1 calc R U . . .
H77C H 0.522236 0.704192 0.314527 0.040 Uiso 1 1 calc R U . . .
C78 C 0.29732(14) 0.69688(5) 0.25068(7) 0.0292(3) Uani 1 1 d . . . . .
H78A H 0.324352 0.723406 0.263356 0.044 Uiso 1 1 calc R U . . .
H78B H 0.265994 0.684084 0.280304 0.044 Uiso 1 1 calc R U . . .
H78C H 0.236330 0.698628 0.215151 0.044 Uiso 1 1 calc R U . . .
S6 S 0.56820(3) 0.58412(2) 0.24370(2) 0.02026(8) Uani 1 1 d . . . . .
O10 O 0.51839(10) 0.56013(3) 0.28521(5) 0.0270(2) Uani 1 1 d . . . . .
C79 C 0.69223(13) 0.55786(5) 0.23400(7) 0.0260(3) Uani 1 1 d . . . . .
H79A H 0.753878 0.558965 0.269346 0.039 Uiso 1 1 calc R U . . .
H79B H 0.720149 0.569809 0.202683 0.039 Uiso 1 1 calc R U . . .
H79C H 0.670958 0.530339 0.224628 0.039 Uiso 1 1 calc R U . . .
C80 C 0.47383(15) 0.57467(5) 0.17561(7) 0.0295(3) Uani 1 1 d . . . . .
H80A H 0.469276 0.546224 0.168585 0.044 Uiso 1 1 calc R U . . .
H80B H 0.504143 0.587689 0.145820 0.044 Uiso 1 1 calc R U . . .
H80C H 0.396056 0.584894 0.174875 0.044 Uiso 1 1 calc R U . . .
S7 S 0.92872(3) 0.69157(2) 0.22340(2) 0.02270(8) Uani 1 1 d . . . . .
O11 O 1.02908(10) 0.68410(4) 0.27482(5) 0.0293(2) Uani 1 1 d . . . . .
C81 C 0.81797(14) 0.65676(5) 0.22814(8) 0.0315(4) Uani 1 1 d . . . . .
H81A H 0.849160 0.630000 0.228539 0.047 Uiso 1 1 calc R U . . .
H81B H 0.751768 0.659846 0.195060 0.047 Uiso 1 1 calc R U . . .
H81C H 0.792310 0.661359 0.263429 0.047 Uiso 1 1 calc R U . . .
C82 C 0.97227(14) 0.66999(5) 0.16467(6) 0.0264(3) Uani 1 1 d . . . . .
H82A H 1.041453 0.683604 0.158727 0.040 Uiso 1 1 calc R U . . .
H82B H 0.909013 0.672351 0.130125 0.040 Uiso 1 1 calc R U . . .
H82C H 0.990405 0.642111 0.172720 0.040 Uiso 1 1 calc R U . . .
S8 S 1.06438(3) 0.55856(2) 0.25875(2) 0.02296(8) Uani 1 1 d . . . . .
O12 O 0.96098(9) 0.56762(4) 0.20960(4) 0.0266(2) Uani 1 1 d . . . . .
C83 C 1.02051(15) 0.57292(6) 0.32127(7) 0.0303(4) Uani 1 1 d . . . . .
H83A H 0.992779 0.600207 0.317155 0.046 Uiso 1 1 calc R U . . .
H83B H 1.086792 0.570866 0.354521 0.046 Uiso 1 1 calc R U . . .
H83C H 0.957698 0.555642 0.326695 0.046 Uiso 1 1 calc R U . . .
C84 C 1.16936(14) 0.59630(5) 0.25825(8) 0.0314(4) Uani 1 1 d . . . . .
H84A H 1.190221 0.596329 0.221204 0.047 Uiso 1 1 calc R U . . .
H84B H 1.239062 0.591333 0.288839 0.047 Uiso 1 1 calc R U . . .
H84C H 1.136375 0.621939 0.264439 0.047 Uiso 1 1 calc R U . . .
S9A S 1.12644(5) 0.59057(2) 0.71106(3) 0.04078(15) Uani 0.8239(10) 1 d D . P A
1
O13A O 1.0508(2) 0.60930(7) 0.74616(11) 0.0678(9) Uani 0.8239(10) 1 d D . P A 1
C87A C 1.2659(5) 0.61129(18) 0.73978(18) 0.0538(10) Uani 0.8239(10) 1 d D . P A
1
H87A H 1.264563 0.639388 0.730356 0.081 Uiso 0.8239(10) 1 calc R U P A 1
H87B H 1.323777 0.597898 0.723361 0.081 Uiso 0.8239(10) 1 calc R U P A 1
H87C H 1.286472 0.608018 0.781455 0.081 Uiso 0.8239(10) 1 calc R U P A 1
C88A C 1.1578(3) 0.54160(9) 0.73827(14) 0.0529(7) Uani 0.8239(10) 1 d D . P A 1
H88A H 1.188497 0.542631 0.779854 0.079 Uiso 0.8239(10) 1 calc R U P A 1
H88B H 1.215630 0.529532 0.720471 0.079 Uiso 0.8239(10) 1 calc R U P A 1
H88C H 1.086283 0.525865 0.729362 0.079 Uiso 0.8239(10) 1 calc R U P A 1
S9B S 1.1500(2) 0.58048(9) 0.76165(12) 0.04078(15) Uani 0.1761(10) 1 d D . P A
2
O13B O 1.0253(10) 0.5949(4) 0.7217(6) 0.0678(9) Uani 0.1761(10) 1 d D . P A 2
C87B C 1.1752(16) 0.5416(4) 0.7173(7) 0.0529(7) Uani 0.1761(10) 1 d D . P A 2
H87D H 1.120206 0.520204 0.718086 0.079 Uiso 0.1761(10) 1 calc R U P A 2
H87E H 1.254964 0.531914 0.731137 0.079 Uiso 0.1761(10) 1 calc R U P A 2
H87F H 1.164493 0.551242 0.677928 0.079 Uiso 0.1761(10) 1 calc R U P A 2
C88B C 1.262(2) 0.6124(9) 0.7514(13) 0.0538(10) Uani 0.1761(10) 1 d D . P A 2
H88D H 1.258550 0.614571 0.710423 0.081 Uiso 0.1761(10) 1 calc R U P A 2
H88E H 1.337738 0.601786 0.771385 0.081 Uiso 0.1761(10) 1 calc R U P A 2
H88F H 1.251259 0.638513 0.766757 0.081 Uiso 0.1761(10) 1 calc R U P A 2
S10 S 0.64239(4) 0.65482(2) 0.70872(2) 0.03045(9) Uani 1 1 d . . . . .
O14 O 0.56117(12) 0.63965(4) 0.74282(6) 0.0429(3) Uani 1 1 d . . . . .
C85 C 0.6976(2) 0.70073(6) 0.74038(9) 0.0491(5) Uani 1 1 d . . . . .
H85A H 0.633745 0.719744 0.735813 0.074 Uiso 1 1 calc R U . . .
H85B H 0.756460 0.710764 0.721458 0.074 Uiso 1 1 calc R U . . .
H85C H 0.732790 0.696820 0.781205 0.074 Uiso 1 1 calc R U . . .
C86 C 0.77399(17) 0.62745(7) 0.73178(9) 0.0426(5) Uani 1 1 d . . . . .
H86A H 0.799627 0.628501 0.773615 0.064 Uiso 1 1 calc R U . . .
H86B H 0.834241 0.638825 0.714918 0.064 Uiso 1 1 calc R U . . .
H86C H 0.760379 0.599991 0.719466 0.064 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 1.4396(11) . ?
S1 N3 1.5656(12) . ?
S1 N4 1.5821(14) . ?
S1 C14 1.7960(16) . ?
F1 C18 1.3474(18) . ?
O2 C12 1.2292(19) . ?
N1 H1 0.91(2) . ?
N1 C9 1.3474(18) . ?
N1 C11 1.3626(18) . ?
N2 C7 1.3459(18) . ?
N2 C11 1.3334(18) . ?
N3 C11 1.3472(19) . ?
N4 C12 1.357(2) . ?
N5 C19 1.148(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C6 1.397(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(2) . ?
C6 C7 1.4814(19) . ?
C7 C8 1.4014(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(2) . ?
C9 C10 1.4898(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.512(2) . ?
C13 C14 1.387(2) . ?
C13 C18 1.383(2) . ?
C14 C15 1.382(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.404(2) . ?
C16 C17 1.397(2) . ?
C16 C19 1.446(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(2) . ?
S2 O3 1.4387(11) . ?
S2 N8 1.5631(13) . ?
S2 N9 1.5858(14) . ?
S2 C37 1.7935(15) . ?
F2 C33 1.3473(17) . ?
O4 C31 1.2273(19) . ?
N6 C26 1.3488(18) . ?
N6 C30 1.3335(18) . ?
N7 H7 0.92(2) . ?
N7 C28 1.3508(19) . ?
N7 C30 1.3590(18) . ?
N8 C30 1.3541(19) . ?
N9 C31 1.364(2) . ?
N10 C38 1.144(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(2) . ?
C20 C25 1.396(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.399(2) . ?
C25 C26 1.4819(19) . ?
C26 C27 1.399(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.376(2) . ?
C28 C29 1.491(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 C32 1.509(2) . ?
C32 C33 1.383(2) . ?
C32 C37 1.389(2) . ?
C33 C34 1.383(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.401(2) . ?
C35 C36 1.405(2) . ?
C35 C38 1.443(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.377(2) . ?
S3 O5 1.4389(11) . ?
S3 N13 1.5657(13) . ?
S3 N14 1.5826(14) . ?
S3 C56 1.7844(15) . ?
F3 C52 1.3431(19) . ?
O6 C50 1.2236(19) . ?
N11 C45 1.3460(18) . ?
N11 C49 1.3358(18) . ?
N12 H12 0.91(2) . ?
N12 C47 1.3509(19) . ?
N12 C49 1.3589(18) . ?
N13 C49 1.3520(18) . ?
N14 C50 1.366(2) . ?
N15 C57 1.146(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.390(2) . ?
C39 C44 1.398(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.392(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.385(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.388(2) . ?
C43 H43 0.9500 . ?
C43 C44 1.399(2) . ?
C44 C45 1.482(2) . ?
C45 C46 1.399(2) . ?
C46 H46 0.9500 . ?
C46 C47 1.377(2) . ?
C47 C48 1.490(2) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C50 C51 1.510(2) . ?
C51 C52 1.380(2) . ?
C51 C56 1.386(2) . ?
C52 C53 1.379(2) . ?
C53 H53 0.9500 . ?
C53 C54 1.394(3) . ?
C54 C55 1.404(2) . ?
C54 C57 1.442(2) . ?
C55 H55 0.9500 . ?
C55 C56 1.378(2) . ?
S4 O7 1.4413(10) . ?
S4 N18 1.5678(12) . ?
S4 N19 1.5807(13) . ?
S4 C75 1.7828(15) . ?
F4 C71 1.3447(18) . ?
O8 C69 1.2232(18) . ?
N16 H16 0.86(2) . ?
N16 C66 1.3481(19) . ?
N16 C68 1.3618(18) . ?
N17 C64 1.3470(18) . ?
N17 C68 1.3342(18) . ?
N18 C68 1.3500(18) . ?
N19 C69 1.363(2) . ?
N20 C76 1.147(2) . ?
C58 H58 0.9500 . ?
C58 C59 1.387(2) . ?
C58 C63 1.398(2) . ?
C59 H59 0.9500 . ?
C59 C60 1.391(2) . ?
C60 H60 0.9500 . ?
C60 C61 1.385(2) . ?
C61 H61 0.9500 . ?
C61 C62 1.390(2) . ?
C62 H62 0.9500 . ?
C62 C63 1.402(2) . ?
C63 C64 1.4796(19) . ?
C64 C65 1.401(2) . ?
C65 H65 0.9500 . ?
C65 C66 1.377(2) . ?
C66 C67 1.4888(19) . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C69 C70 1.514(2) . ?
C70 C71 1.382(2) . ?
C70 C75 1.388(2) . ?
C71 C72 1.384(2) . ?
C72 H72 0.9500 . ?
C72 C73 1.396(2) . ?
C73 C74 1.400(2) . ?
C73 C76 1.444(2) . ?
C74 H74 0.9500 . ?
C74 C75 1.382(2) . ?
S5 O9 1.5138(11) . ?
S5 C77 1.7789(16) . ?
S5 C78 1.7812(16) . ?
C77 H77A 0.9800 . ?
C77 H77B 0.9800 . ?
C77 H77C 0.9800 . ?
C78 H78A 0.9800 . ?
C78 H78B 0.9800 . ?
C78 H78C 0.9800 . ?
S6 O10 1.5131(11) . ?
S6 C79 1.7799(16) . ?
S6 C80 1.7776(16) . ?
C79 H79A 0.9800 . ?
C79 H79B 0.9800 . ?
C79 H79C 0.9800 . ?
C80 H80A 0.9800 . ?
C80 H80B 0.9800 . ?
C80 H80C 0.9800 . ?
S7 O11 1.5177(12) . ?
S7 C81 1.7888(17) . ?
S7 C82 1.7737(16) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
S8 O12 1.5163(11) . ?
S8 C83 1.7728(16) . ?
S8 C84 1.7872(17) . ?
C83 H83A 0.9800 . ?
C83 H83B 0.9800 . ?
C83 H83C 0.9800 . ?
C84 H84A 0.9800 . ?
C84 H84B 0.9800 . ?
C84 H84C 0.9800 . ?
S9A O13A 1.510(2) . ?
S9A C87A 1.776(5) . ?
S9A C88A 1.793(3) . ?
C87A H87A 0.9800 . ?
C87A H87B 0.9800 . ?
C87A H87C 0.9800 . ?
C88A H88A 0.9800 . ?
C88A H88B 0.9800 . ?
C88A H88C 0.9800 . ?
S9B O13B 1.633(12) . ?
S9B C87B 1.767(13) . ?
S9B C88B 1.773(17) . ?
C87B H87D 0.9800 . ?
C87B H87E 0.9800 . ?
C87B H87F 0.9800 . ?
C88B H88D 0.9800 . ?
C88B H88E 0.9800 . ?
C88B H88F 0.9800 . ?
S10 O14 1.4962(13) . ?
S10 C85 1.789(2) . ?
S10 C86 1.785(2) . ?
C85 H85A 0.9800 . ?
C85 H85B 0.9800 . ?
C85 H85C 0.9800 . ?
C86 H86A 0.9800 . ?
C86 H86B 0.9800 . ?
C86 H86C 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
O1 S1 N3 107.28(7) . . ?
O1 S1 N4 115.33(7) . . ?
O1 S1 C14 109.27(7) . . ?
N3 S1 N4 110.65(7) . . ?
N3 S1 C14 116.97(7) . . ?
N4 S1 C14 97.44(7) . . ?
C9 N1 H1 119.7(13) . . ?
C9 N1 C11 121.69(12) . . ?
C11 N1 H1 118.6(13) . . ?
C11 N2 C7 118.26(12) . . ?
C11 N3 S1 121.55(10) . . ?
C12 N4 S1 112.86(11) . . ?
C2 C1 H1A 119.6 . . ?
C2 C1 C6 120.72(15) . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.72(15) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.11(15) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.41(15) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.95(14) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.09(13) . . ?
C1 C6 C7 119.25(13) . . ?
C5 C6 C7 121.65(13) . . ?
N2 C7 C6 115.81(12) . . ?
N2 C7 C8 121.95(13) . . ?
C8 C7 C6 122.23(13) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.22(13) . . ?
C9 C8 H8 120.9 . . ?
N1 C9 C8 118.41(13) . . ?
N1 C9 C10 117.81(13) . . ?
C8 C9 C10 123.77(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 N1 121.42(13) . . ?
N2 C11 N3 124.05(13) . . ?
N3 C11 N1 114.47(13) . . ?
O2 C12 N4 124.76(14) . . ?
O2 C12 C13 122.98(14) . . ?
N4 C12 C13 112.22(13) . . ?
C14 C13 C12 111.90(13) . . ?
C18 C13 C12 129.74(14) . . ?
C18 C13 C14 118.33(14) . . ?
C13 C14 S1 105.40(11) . . ?
C15 C14 S1 131.06(12) . . ?
C15 C14 C13 123.51(15) . . ?
C14 C15 H15 122.0 . . ?
C14 C15 C16 116.01(15) . . ?
C16 C15 H15 122.0 . . ?
C15 C16 C19 120.92(16) . . ?
C17 C16 C15 122.37(15) . . ?
C17 C16 C19 116.71(16) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.49(15) . . ?
C18 C17 H17 120.8 . . ?
F1 C18 C13 120.74(14) . . ?
F1 C18 C17 117.97(14) . . ?
C17 C18 C13 121.29(15) . . ?
N5 C19 C16 176.9(2) . . ?
O3 S2 N8 107.53(7) . . ?
O3 S2 N9 115.54(7) . . ?
O3 S2 C37 108.93(7) . . ?
N8 S2 N9 110.25(7) . . ?
N8 S2 C37 117.35(7) . . ?
N9 S2 C37 97.34(7) . . ?
C30 N6 C26 118.31(12) . . ?
C28 N7 H7 120.8(14) . . ?
C28 N7 C30 121.33(12) . . ?
C30 N7 H7 117.8(14) . . ?
C30 N8 S2 120.15(10) . . ?
C31 N9 S2 112.72(11) . . ?
C21 C20 H20 119.6 . . ?
C21 C20 C25 120.82(14) . . ?
C25 C20 H20 119.6 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.77(15) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 119.95(14) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.45(15) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.96(14) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 C24 119.04(13) . . ?
C20 C25 C26 119.36(13) . . ?
C24 C25 C26 121.58(13) . . ?
N6 C26 C25 115.62(12) . . ?
N6 C26 C27 121.64(13) . . ?
C27 C26 C25 122.73(13) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 C26 118.43(13) . . ?
C28 C27 H27 120.8 . . ?
N7 C28 C27 118.54(13) . . ?
N7 C28 C29 117.55(13) . . ?
C27 C28 C29 123.91(14) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N6 C30 N7 121.70(13) . . ?
N6 C30 N8 123.39(13) . . ?
N8 C30 N7 114.88(12) . . ?
O4 C31 N9 124.63(14) . . ?
O4 C31 C32 123.23(14) . . ?
N9 C31 C32 112.09(13) . . ?
C33 C32 C31 130.34(14) . . ?
C33 C32 C37 117.70(14) . . ?
C37 C32 C31 111.90(13) . . ?
F2 C33 C32 120.38(14) . . ?
F2 C33 C34 118.20(13) . . ?
C34 C33 C32 121.42(14) . . ?
C33 C34 H34 120.7 . . ?
C33 C34 C35 118.57(14) . . ?
C35 C34 H34 120.7 . . ?
C34 C35 C36 122.20(14) . . ?
C34 C35 C38 117.69(15) . . ?
C36 C35 C38 120.09(14) . . ?
C35 C36 H36 122.1 . . ?
C37 C36 C35 115.72(14) . . ?
C37 C36 H36 122.1 . . ?
C32 C37 S2 105.56(11) . . ?
C36 C37 S2 130.06(12) . . ?
C36 C37 C32 124.36(14) . . ?
N10 C38 C35 177.8(2) . . ?
O5 S3 N13 107.51(7) . . ?
O5 S3 N14 115.79(7) . . ?
O5 S3 C56 108.90(7) . . ?
N13 S3 N14 110.72(7) . . ?
N13 S3 C56 116.34(7) . . ?
N14 S3 C56 97.66(7) . . ?
C49 N11 C45 118.32(12) . . ?
C47 N12 H12 121.0(13) . . ?
C47 N12 C49 121.35(13) . . ?
C49 N12 H12 117.5(13) . . ?
C49 N13 S3 119.57(10) . . ?
C50 N14 S3 112.69(11) . . ?
C40 C39 H39 119.7 . . ?
C40 C39 C44 120.61(14) . . ?
C44 C39 H39 119.7 . . ?
C39 C40 H40 120.1 . . ?
C39 C40 C41 119.89(16) . . ?
C41 C40 H40 120.1 . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.78(15) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.59(15) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 119.9 . . ?
C42 C43 C44 120.11(15) . . ?
C44 C43 H43 119.9 . . ?
C39 C44 C43 118.97(14) . . ?
C39 C44 C45 119.43(13) . . ?
C43 C44 C45 121.59(14) . . ?
N11 C45 C44 115.62(13) . . ?
N11 C45 C46 121.66(13) . . ?
C46 C45 C44 122.72(13) . . ?
C45 C46 H46 120.7 . . ?
C47 C46 C45 118.53(13) . . ?
C47 C46 H46 120.7 . . ?
N12 C47 C46 118.41(13) . . ?
N12 C47 C48 117.38(13) . . ?
C46 C47 C48 124.21(14) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N11 C49 N12 121.71(13) . . ?
N11 C49 N13 123.55(13) . . ?
N13 C49 N12 114.73(13) . . ?
O6 C50 N14 124.80(15) . . ?
O6 C50 C51 123.36(15) . . ?
N14 C50 C51 111.83(13) . . ?
C52 C51 C50 130.00(14) . . ?
C52 C51 C56 118.00(15) . . ?
C56 C51 C50 111.97(13) . . ?
F3 C52 C51 120.31(15) . . ?
F3 C52 C53 118.67(15) . . ?
C53 C52 C51 121.01(15) . . ?
C52 C53 H53 120.5 . . ?
C52 C53 C54 119.06(15) . . ?
C54 C53 H53 120.5 . . ?
C53 C54 C55 122.07(15) . . ?
C53 C54 C57 117.69(16) . . ?
C55 C54 C57 120.23(16) . . ?
C54 C55 H55 122.2 . . ?
C56 C55 C54 115.69(15) . . ?
C56 C55 H55 122.2 . . ?
C51 C56 S3 105.71(11) . . ?
C55 C56 S3 130.09(12) . . ?
C55 C56 C51 124.16(14) . . ?
N15 C57 C54 177.8(2) . . ?
O7 S4 N18 107.08(6) . . ?
O7 S4 N19 115.37(7) . . ?
O7 S4 C75 109.56(6) . . ?
N18 S4 N19 111.29(7) . . ?
N18 S4 C75 115.67(7) . . ?
N19 S4 C75 97.98(7) . . ?
C66 N16 H16 121.1(13) . . ?
C66 N16 C68 121.70(13) . . ?
C68 N16 H16 117.2(13) . . ?
C68 N17 C64 118.28(12) . . ?
C68 N18 S4 120.36(10) . . ?
C69 N19 S4 112.56(10) . . ?
C59 C58 H58 119.7 . . ?
C59 C58 C63 120.61(14) . . ?
C63 C58 H58 119.7 . . ?
C58 C59 H59 120.0 . . ?
C58 C59 C60 120.05(15) . . ?
C60 C59 H59 120.0 . . ?
C59 C60 H60 120.1 . . ?
C61 C60 C59 119.78(15) . . ?
C61 C60 H60 120.1 . . ?
C60 C61 H61 119.7 . . ?
C60 C61 C62 120.62(15) . . ?
C62 C61 H61 119.7 . . ?
C61 C62 H62 120.0 . . ?
C61 C62 C63 119.96(14) . . ?
C63 C62 H62 120.0 . . ?
C58 C63 C62 118.95(14) . . ?
C58 C63 C64 119.46(13) . . ?
C62 C63 C64 121.59(13) . . ?
N17 C64 C63 115.62(12) . . ?
N17 C64 C65 121.78(13) . . ?
C65 C64 C63 122.59(13) . . ?
C64 C65 H65 120.8 . . ?
C66 C65 C64 118.44(13) . . ?
C66 C65 H65 120.8 . . ?
N16 C66 C65 118.30(13) . . ?
N16 C66 C67 117.57(13) . . ?
C65 C66 C67 124.13(13) . . ?
C66 C67 H67A 109.5 . . ?
C66 C67 H67B 109.5 . . ?
C66 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
N17 C68 N16 121.48(13) . . ?
N17 C68 N18 124.17(13) . . ?
N18 C68 N16 114.33(12) . . ?
O8 C69 N19 125.07(14) . . ?
O8 C69 C70 122.97(14) . . ?
N19 C69 C70 111.95(12) . . ?
C71 C70 C69 130.23(14) . . ?
C71 C70 C75 117.87(14) . . ?
C75 C70 C69 111.88(13) . . ?
F4 C71 C70 120.52(15) . . ?
F4 C71 C72 118.51(14) . . ?
C70 C71 C72 120.97(14) . . ?
C71 C72 H72 120.5 . . ?
C71 C72 C73 119.10(14) . . ?
C73 C72 H72 120.5 . . ?
C72 C73 C74 122.04(14) . . ?
C72 C73 C76 117.71(15) . . ?
C74 C73 C76 120.19(16) . . ?
C73 C74 H74 122.1 . . ?
C75 C74 C73 115.80(14) . . ?
C75 C74 H74 122.1 . . ?
C70 C75 S4 105.56(11) . . ?
C74 C75 S4 130.20(12) . . ?
C74 C75 C70 124.21(14) . . ?
N20 C76 C73 176.5(2) . . ?
O9 S5 C77 104.82(7) . . ?
O9 S5 C78 106.12(7) . . ?
C77 S5 C78 97.97(8) . . ?
S5 C77 H77A 109.5 . . ?
S5 C77 H77B 109.5 . . ?
S5 C77 H77C 109.5 . . ?
H77A C77 H77B 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
S5 C78 H78A 109.5 . . ?
S5 C78 H78B 109.5 . . ?
S5 C78 H78C 109.5 . . ?
H78A C78 H78B 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
O10 S6 C79 106.28(7) . . ?
O10 S6 C80 104.66(7) . . ?
C80 S6 C79 98.34(8) . . ?
S6 C79 H79A 109.5 . . ?
S6 C79 H79B 109.5 . . ?
S6 C79 H79C 109.5 . . ?
H79A C79 H79B 109.5 . . ?
H79A C79 H79C 109.5 . . ?
H79B C79 H79C 109.5 . . ?
S6 C80 H80A 109.5 . . ?
S6 C80 H80B 109.5 . . ?
S6 C80 H80C 109.5 . . ?
H80A C80 H80B 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 109.5 . . ?
O11 S7 C81 106.28(8) . . ?
O11 S7 C82 105.10(7) . . ?
C82 S7 C81 97.74(8) . . ?
S7 C81 H81A 109.5 . . ?
S7 C81 H81B 109.5 . . ?
S7 C81 H81C 109.5 . . ?
H81A C81 H81B 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
S7 C82 H82A 109.5 . . ?
S7 C82 H82B 109.5 . . ?
S7 C82 H82C 109.5 . . ?
H82A C82 H82B 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
O12 S8 C83 105.09(7) . . ?
O12 S8 C84 106.39(7) . . ?
C83 S8 C84 98.82(8) . . ?
S8 C83 H83A 109.5 . . ?
S8 C83 H83B 109.5 . . ?
S8 C83 H83C 109.5 . . ?
H83A C83 H83B 109.5 . . ?
H83A C83 H83C 109.5 . . ?
H83B C83 H83C 109.5 . . ?
S8 C84 H84A 109.5 . . ?
S8 C84 H84B 109.5 . . ?
S8 C84 H84C 109.5 . . ?
H84A C84 H84B 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
O13A S9A C87A 103.7(2) . . ?
O13A S9A C88A 106.56(13) . . ?
C87A S9A C88A 97.7(2) . . ?
S9A C87A H87A 109.5 . . ?
S9A C87A H87B 109.5 . . ?
S9A C87A H87C 109.5 . . ?
H87A C87A H87B 109.5 . . ?
H87A C87A H87C 109.5 . . ?
H87B C87A H87C 109.5 . . ?
S9A C88A H88A 109.5 . . ?
S9A C88A H88B 109.5 . . ?
S9A C88A H88C 109.5 . . ?
H88A C88A H88B 109.5 . . ?
H88A C88A H88C 109.5 . . ?
H88B C88A H88C 109.5 . . ?
O13B S9B C87B 97.3(8) . . ?
O13B S9B C88B 109.6(13) . . ?
C87B S9B C88B 97.7(11) . . ?
S9B C87B H87D 109.5 . . ?
S9B C87B H87E 109.5 . . ?
S9B C87B H87F 109.5 . . ?
H87D C87B H87E 109.5 . . ?
H87D C87B H87F 109.5 . . ?
H87E C87B H87F 109.5 . . ?
S9B C88B H88D 109.5 . . ?
S9B C88B H88E 109.5 . . ?
S9B C88B H88F 109.5 . . ?
H88D C88B H88E 109.5 . . ?
H88D C88B H88F 109.5 . . ?
H88E C88B H88F 109.5 . . ?
O14 S10 C85 106.49(9) . . ?
O14 S10 C86 106.11(9) . . ?
C86 S10 C85 96.82(11) . . ?
S10 C85 H85A 109.5 . . ?
S10 C85 H85B 109.5 . . ?
S10 C85 H85C 109.5 . . ?
H85A C85 H85B 109.5 . . ?
H85A C85 H85C 109.5 . . ?
H85B C85 H85C 109.5 . . ?
S10 C86 H86A 109.5 . . ?
S10 C86 H86B 109.5 . . ?
S10 C86 H86C 109.5 . . ?
H86A C86 H86B 109.5 . . ?
H86A C86 H86C 109.5 . . ?
H86B C86 H86C 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 N3 C11 N1 -158.64(11) . . . . ?
S1 N3 C11 N2 24.1(2) . . . . ?
S1 N4 C12 O2 179.03(12) . . . . ?
S1 N4 C12 C13 1.14(15) . . . . ?
S1 C14 C15 C16 -178.22(12) . . . . ?
O1 S1 N3 C11 -175.44(12) . . . . ?
O1 S1 N4 C12 112.44(11) . . . . ?
O1 S1 C14 C13 -116.11(11) . . . . ?
O1 S1 C14 C15 62.06(16) . . . . ?
O2 C12 C13 C14 -175.84(14) . . . . ?
O2 C12 C13 C18 1.8(2) . . . . ?
N2 C7 C8 C9 0.4(2) . . . . ?
N3 S1 N4 C12 -125.58(11) . . . . ?
N3 S1 C14 C13 121.82(11) . . . . ?
N3 S1 C14 C15 -60.01(17) . . . . ?
N4 S1 N3 C11 57.97(14) . . . . ?
N4 S1 C14 C13 4.07(11) . . . . ?
N4 S1 C14 C15 -177.75(15) . . . . ?
N4 C12 C13 C14 2.10(17) . . . . ?
N4 C12 C13 C18 179.74(15) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C7 N2 8.20(19) . . . . ?
C1 C6 C7 C8 -170.57(14) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C6 C7 178.62(14) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 -178.61(14) . . . . ?
C5 C6 C7 N2 -173.27(13) . . . . ?
C5 C6 C7 C8 8.0(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C7 C8 C9 179.13(13) . . . . ?
C7 N2 C11 N1 -2.7(2) . . . . ?
C7 N2 C11 N3 174.32(14) . . . . ?
C7 C8 C9 N1 -1.0(2) . . . . ?
C7 C8 C9 C10 179.50(14) . . . . ?
C9 N1 C11 N2 2.2(2) . . . . ?
C9 N1 C11 N3 -175.13(13) . . . . ?
C11 N1 C9 C8 -0.2(2) . . . . ?
C11 N1 C9 C10 179.28(13) . . . . ?
C11 N2 C7 C6 -177.33(12) . . . . ?
C11 N2 C7 C8 1.4(2) . . . . ?
C12 C13 C14 S1 -3.84(14) . . . . ?
C12 C13 C14 C15 177.81(13) . . . . ?
C12 C13 C18 F1 2.4(2) . . . . ?
C12 C13 C18 C17 -176.78(15) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 S1 N3 C11 -52.34(15) . . . . ?
C14 S1 N4 C12 -3.04(12) . . . . ?
C14 C13 C18 F1 179.95(13) . . . . ?
C14 C13 C18 C17 0.7(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C14 C15 C16 C19 -179.78(15) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C16 C17 C18 F1 179.94(14) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
C18 C13 C14 S1 178.22(12) . . . . ?
C18 C13 C14 C15 -0.1(2) . . . . ?
C19 C16 C17 C18 -179.66(15) . . . . ?
S2 N8 C30 N6 -29.0(2) . . . . ?
S2 N8 C30 N7 152.96(11) . . . . ?
S2 N9 C31 O4 179.36(12) . . . . ?
S2 N9 C31 C32 -2.92(15) . . . . ?
F2 C33 C34 C35 179.90(13) . . . . ?
O3 S2 N8 C30 178.64(12) . . . . ?
O3 S2 N9 C31 -109.87(11) . . . . ?
O3 S2 C37 C32 114.24(11) . . . . ?
O3 S2 C37 C36 -64.19(15) . . . . ?
O4 C31 C32 C33 -0.9(2) . . . . ?
O4 C31 C32 C37 175.93(14) . . . . ?
N6 C26 C27 C28 -0.2(2) . . . . ?
N8 S2 N9 C31 127.98(11) . . . . ?
N8 S2 C37 C32 -123.36(10) . . . . ?
N8 S2 C37 C36 58.21(16) . . . . ?
N9 S2 N8 C30 -54.60(14) . . . . ?
N9 S2 C37 C32 -6.00(11) . . . . ?
N9 S2 C37 C36 175.56(14) . . . . ?
N9 C31 C32 C33 -178.71(15) . . . . ?
N9 C31 C32 C37 -1.83(17) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C20 C25 C26 N6 -2.79(19) . . . . ?
C20 C25 C26 C27 176.16(14) . . . . ?
C21 C20 C25 C24 -0.4(2) . . . . ?
C21 C20 C25 C26 -178.93(14) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C23 C24 C25 C20 0.2(2) . . . . ?
C23 C24 C25 C26 178.63(14) . . . . ?
C24 C25 C26 N6 178.75(13) . . . . ?
C24 C25 C26 C27 -2.3(2) . . . . ?
C25 C20 C21 C22 0.2(2) . . . . ?
C25 C26 C27 C28 -179.10(13) . . . . ?
C26 N6 C30 N7 2.4(2) . . . . ?
C26 N6 C30 N8 -175.58(13) . . . . ?
C26 C27 C28 N7 1.5(2) . . . . ?
C26 C27 C28 C29 -178.97(14) . . . . ?
C28 N7 C30 N6 -1.1(2) . . . . ?
C28 N7 C30 N8 177.00(13) . . . . ?
C30 N6 C26 C25 177.26(12) . . . . ?
C30 N6 C26 C27 -1.7(2) . . . . ?
C30 N7 C28 C27 -0.9(2) . . . . ?
C30 N7 C28 C29 179.55(13) . . . . ?
C31 C32 C33 F2 -3.9(2) . . . . ?
C31 C32 C33 C34 174.98(14) . . . . ?
C31 C32 C37 S2 5.00(14) . . . . ?
C31 C32 C37 C36 -176.45(13) . . . . ?
C32 C33 C34 C35 1.0(2) . . . . ?
C33 C32 C37 S2 -177.69(11) . . . . ?
C33 C32 C37 C36 0.9(2) . . . . ?
C33 C34 C35 C36 0.7(2) . . . . ?
C33 C34 C35 C38 -177.97(15) . . . . ?
C34 C35 C36 C37 -1.5(2) . . . . ?
C35 C36 C37 S2 178.89(12) . . . . ?
C35 C36 C37 C32 0.7(2) . . . . ?
C37 S2 N8 C30 55.52(14) . . . . ?
C37 S2 N9 C31 5.21(12) . . . . ?
C37 C32 C33 F2 179.39(13) . . . . ?
C37 C32 C33 C34 -1.7(2) . . . . ?
C38 C35 C36 C37 177.13(14) . . . . ?
S3 N13 C49 N11 -27.2(2) . . . . ?
S3 N13 C49 N12 154.14(11) . . . . ?
S3 N14 C50 O6 -177.97(12) . . . . ?
S3 N14 C50 C51 0.93(15) . . . . ?
F3 C52 C53 C54 179.10(15) . . . . ?
O5 S3 N13 C49 -178.06(12) . . . . ?
O5 S3 N14 C50 -114.11(11) . . . . ?
O5 S3 C56 C51 117.56(11) . . . . ?
O5 S3 C56 C55 -60.14(16) . . . . ?
O6 C50 C51 C52 -2.5(3) . . . . ?
O6 C50 C51 C56 175.52(14) . . . . ?
N11 C45 C46 C47 -0.4(2) . . . . ?
N13 S3 N14 C50 123.20(11) . . . . ?
N13 S3 C56 C51 -120.82(10) . . . . ?
N13 S3 C56 C55 61.49(16) . . . . ?
N14 S3 N13 C49 -50.68(14) . . . . ?
N14 S3 C56 C51 -3.11(11) . . . . ?
N14 S3 C56 C55 179.19(14) . . . . ?
N14 C50 C51 C52 178.57(15) . . . . ?
N14 C50 C51 C56 -3.40(17) . . . . ?
C39 C40 C41 C42 1.8(2) . . . . ?
C39 C44 C45 N11 -10.03(19) . . . . ?
C39 C44 C45 C46 170.19(13) . . . . ?
C40 C39 C44 C43 -1.7(2) . . . . ?
C40 C39 C44 C45 177.09(14) . . . . ?
C40 C41 C42 C43 -1.2(3) . . . . ?
C41 C42 C43 C44 -0.7(2) . . . . ?
C42 C43 C44 C39 2.2(2) . . . . ?
C42 C43 C44 C45 -176.53(14) . . . . ?
C43 C44 C45 N11 168.68(13) . . . . ?
C43 C44 C45 C46 -11.1(2) . . . . ?
C44 C39 C40 C41 -0.3(2) . . . . ?
C44 C45 C46 C47 179.41(13) . . . . ?
C45 N11 C49 N12 0.7(2) . . . . ?
C45 N11 C49 N13 -177.85(13) . . . . ?
C45 C46 C47 N12 1.3(2) . . . . ?
C45 C46 C47 C48 -179.08(13) . . . . ?
C47 N12 C49 N11 0.2(2) . . . . ?
C47 N12 C49 N13 178.91(13) . . . . ?
C49 N11 C45 C44 179.57(12) . . . . ?
C49 N11 C45 C46 -0.6(2) . . . . ?
C49 N12 C47 C46 -1.2(2) . . . . ?
C49 N12 C47 C48 179.10(13) . . . . ?
C50 C51 C52 F3 -1.3(3) . . . . ?
C50 C51 C52 C53 178.05(15) . . . . ?
C50 C51 C56 S3 3.91(14) . . . . ?
C50 C51 C56 C55 -178.22(13) . . . . ?
C51 C52 C53 C54 -0.2(2) . . . . ?
C52 C51 C56 S3 -177.80(12) . . . . ?
C52 C51 C56 C55 0.1(2) . . . . ?
C52 C53 C54 C55 0.2(3) . . . . ?
C52 C53 C54 C57 -179.69(16) . . . . ?
C53 C54 C55 C56 0.0(2) . . . . ?
C54 C55 C56 S3 177.19(12) . . . . ?
C54 C55 C56 C51 -0.1(2) . . . . ?
C56 S3 N13 C49 59.58(14) . . . . ?
C56 S3 N14 C50 1.23(12) . . . . ?
C56 C51 C52 F3 -179.21(14) . . . . ?
C56 C51 C52 C53 0.1(2) . . . . ?
C57 C54 C55 C56 179.87(15) . . . . ?
S4 N18 C68 N16 -160.09(10) . . . . ?
S4 N18 C68 N17 21.7(2) . . . . ?
S4 N19 C69 O8 177.25(12) . . . . ?
S4 N19 C69 C70 -1.32(15) . . . . ?
F4 C71 C72 C73 -179.75(13) . . . . ?
O7 S4 N18 C68 -177.78(11) . . . . ?
O7 S4 N19 C69 115.87(11) . . . . ?
O7 S4 C75 C70 -118.73(10) . . . . ?
O7 S4 C75 C74 59.25(15) . . . . ?
O8 C69 C70 C71 2.6(2) . . . . ?
O8 C69 C70 C75 -175.81(13) . . . . ?
N17 C64 C65 C66 0.5(2) . . . . ?
N18 S4 N19 C69 -121.88(10) . . . . ?
N18 S4 C75 C70 120.17(10) . . . . ?
N18 S4 C75 C74 -61.85(15) . . . . ?
N19 S4 N18 C68 55.29(14) . . . . ?
N19 S4 C75 C70 1.86(11) . . . . ?
N19 S4 C75 C74 179.85(14) . . . . ?
N19 C69 C70 C71 -178.83(14) . . . . ?
N19 C69 C70 C75 2.80(17) . . . . ?
C58 C59 C60 C61 -1.3(3) . . . . ?
C58 C63 C64 N17 16.72(19) . . . . ?
C58 C63 C64 C65 -162.89(14) . . . . ?
C59 C58 C63 C62 1.4(2) . . . . ?
C59 C58 C63 C64 -178.06(14) . . . . ?
C59 C60 C61 C62 0.6(3) . . . . ?
C60 C61 C62 C63 1.1(2) . . . . ?
C61 C62 C63 C58 -2.1(2) . . . . ?
C61 C62 C63 C64 177.40(14) . . . . ?
C62 C63 C64 N17 -162.74(13) . . . . ?
C62 C63 C64 C65 17.7(2) . . . . ?
C63 C58 C59 C60 0.3(3) . . . . ?
C63 C64 C65 C66 -179.90(13) . . . . ?
C64 N17 C68 N16 -1.7(2) . . . . ?
C64 N17 C68 N18 176.46(13) . . . . ?
C64 C65 C66 N16 -0.6(2) . . . . ?
C64 C65 C66 C67 -179.87(13) . . . . ?
C66 N16 C68 N17 1.7(2) . . . . ?
C66 N16 C68 N18 -176.65(13) . . . . ?
C68 N16 C66 C65 -0.5(2) . . . . ?
C68 N16 C66 C67 178.88(13) . . . . ?
C68 N17 C64 C63 -179.01(12) . . . . ?
C68 N17 C64 C65 0.6(2) . . . . ?
C69 C70 C71 F4 0.9(2) . . . . ?
C69 C70 C71 C72 -178.78(14) . . . . ?
C69 C70 C75 S4 -2.75(14) . . . . ?
C69 C70 C75 C74 179.11(13) . . . . ?
C70 C71 C72 C73 -0.1(2) . . . . ?
C71 C70 C75 S4 178.66(11) . . . . ?
C71 C70 C75 C74 0.5(2) . . . . ?
C71 C72 C73 C74 0.7(2) . . . . ?
C71 C72 C73 C76 -176.61(14) . . . . ?
C72 C73 C74 C75 -0.7(2) . . . . ?
C73 C74 C75 S4 -177.60(11) . . . . ?
C73 C74 C75 C70 0.0(2) . . . . ?
C75 S4 N18 C68 -55.35(14) . . . . ?
C75 S4 N19 C69 -0.27(11) . . . . ?
C75 C70 C71 F4 179.17(13) . . . . ?
C75 C70 C71 C72 -0.5(2) . . . . ?
C76 C73 C74 C75 176.57(14) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_67
_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 1.543
_oxdiff_exptl_absorpt_empirical_full_min 0.801
####################################################################### 
# 
# 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_en13605-22_dmso
_database_code_depnum_ccdc_archive 'CCDC 2517067'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Br Cl N4 O2 S'
_chemical_formula_sum            'C18 H12 Br Cl N4 O2 S'
_chemical_formula_weight         463.74
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.8880(3)
_cell_length_b                   12.47300(10)
_cell_length_c                   12.9999(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.1320(10)
_cell_angle_gamma                90
_cell_volume                     3582.56(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1690
_cell_measurement_theta_min      3.9790
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.509
_exptl_absorpt_coefficient_mu    5.792
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -4 -3 0.0169
-5 0 1 0.0493
5 0 -2 0.0763
-5 4 -5 0.0147
5 -4 5 0.0083
5 5 3 0.0078
-5 3 5 0.0448
-5 3 -1 0.0273
5 -1 -5 0.0711

_exptl_crystal_preparation       
'The material was recrystallized from DMSO by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow evaporation'
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.023
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23294
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.297
_diffrn_reflns_theta_min         4.002
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  86.00   0.50    1.00    --   50.45 -93.00-106.00  198
  2  ω    -80.00  17.00   0.50    1.00    --  -51.01  93.00   4.00  194
  3  ω    -80.00 -12.00   0.50    3.00    --  -79.95  93.00   4.00  136
  4  ω   -148.00 -83.00   0.50    3.00    --  -79.95 -93.00-106.00  130
  5  ω    104.00 164.00   0.50    3.00    --   96.59  93.00   4.00  120
  6  ω     29.00 106.00   0.50    3.00    --   96.59 -93.00-106.00  154
  7  ω     41.00 105.00   0.50    3.00    --  108.39 -93.00-106.00  128
  8  ω    104.00 176.00   0.50    3.00    --  108.39  93.00   4.00  144
  9  ω     80.00 119.00   0.50    1.00    --   50.45  77.00  30.00   78
 10  ω   -119.00 -80.00   0.50    1.00    --  -51.01 -77.00 -90.00   78
 11  ω   -119.00 -80.00   0.50    1.00    --  -51.01 -77.00 -60.00   78
 12  ω   -119.00 -80.00   0.50    1.00    --  -51.01 -77.00  60.00   78
 13  ω   -148.00 -80.00   0.50    3.00    --  -79.95 -77.00   0.00  136
 14  ω     34.00 112.00   0.50    3.00    --   96.59-125.00-120.00  156
 15  ω     34.00 112.00   0.50    3.00    --   96.59-125.00  90.00  156
 16  ω     19.00 113.00   0.50    3.00    --   96.59 -45.00  90.00  188
 17  ω     28.00 105.00   0.50    3.00    --   96.59 -95.00   0.00  154
 18  ω     80.00 165.00   0.50    3.00    --   96.59  77.00 -60.00  170
 19  ω     95.00 178.00   0.50    3.00    --  108.39 125.00 -60.00  166
 20  ω   -126.00 -31.00   0.50    1.00    --  -51.01 -57.00 -60.00  190
 21  ω   -126.00 -31.00   0.50    1.00    --  -51.01 -57.00 120.00  190
 22  ω   -126.00 -31.00   0.50    1.00    --  -51.01 -57.00  30.00  190
 23  ω   -125.00 -76.00   0.50    1.00    --  -51.01-125.00-180.00   98
 24  ω   -126.00 -31.00   0.50    1.00    --  -51.01 -57.00-180.00  190
 25  ω     76.00 176.00   0.50    3.00    --   96.59  30.00 120.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3242
_reflns_number_total             3636
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         1.089
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.184
_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)+(0.0631P)²+14.9537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          
'Cl and Br was refined to have disorder with occupancy approximately 0.58:0.42 meaning that two regioisomer coexists and manifested as subtitutional disorder'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1B-C16 = Cl1A-C14
 1.73 with sigma of 0.002
 Br1B-C14 = Br1A-C16
 1.875 with sigma of 0.002
 C15-Br1A \\sim Br1A-C17
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Br1A \\sim Cl1B: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
Uanis(Br1A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(Cl1B) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(Br1B)=Sof(Cl1B)=1-FVAR(1)
 Sof(Cl1A)=Sof(Br1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C1(H1), C2(H2), C3(H3), C4(H4A), C5(H5), C8(H8), C17(H17), C15(H15)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.4957(5) 0.1099(4) 0.5840(10) 0.0379(12) Uani 0.582(2) 1 d D . P A 1
Br1A Br 0.45882(10) 0.54054(13) 0.5993(2) 0.0533(6) Uani 0.582(2) 1 d D U P A 1
S1 S 0.68259(3) 0.33507(6) 0.79225(6) 0.02232(18) Uani 1 1 d . . . . .
O1 O 0.68511(11) 0.36171(19) 0.90082(18) 0.0340(5) Uani 1 1 d . . . . .
O2 O 0.63299(9) 0.06882(16) 0.69747(17) 0.0233(4) Uani 1 1 d . . . . .
N1 N 0.69058(11) 0.21088(19) 0.7727(2) 0.0221(5) Uani 1 1 d . . . . .
N2 N 0.72880(12) 0.4077(2) 0.7546(2) 0.0245(5) Uani 1 1 d . . . . .
N3 N 0.69626(10) 0.35104(18) 0.57349(19) 0.0186(5) Uani 1 1 d . . . . .
N4 N 0.77851(11) 0.46737(18) 0.63625(19) 0.0193(5) Uani 1 1 d . . . . .
H4 H 0.801923 0.502026 0.690518 0.023 Uiso 1 1 calc R U . . .
C1 C 0.61951(13) 0.2326(2) 0.4110(3) 0.0254(6) Uani 1 1 d . . . . .
H1 H 0.615190 0.229158 0.481607 0.030 Uiso 1 1 calc R U . . .
C2 C 0.58109(14) 0.1729(3) 0.3305(3) 0.0338(8) Uani 1 1 d . . . . .
H2 H 0.550549 0.129232 0.346248 0.041 Uiso 1 1 calc R U . . .
C3 C 0.58752(14) 0.1774(3) 0.2266(3) 0.0337(8) Uani 1 1 d . . . . .
H3 H 0.561762 0.135933 0.171891 0.040 Uiso 1 1 calc R U . . .
C4 C 0.63142(15) 0.2422(3) 0.2037(3) 0.0324(7) Uani 1 1 d . . . . .
H4A H 0.635405 0.246239 0.132864 0.039 Uiso 1 1 calc R U . . .
C5 C 0.66991(14) 0.3018(3) 0.2844(3) 0.0270(6) Uani 1 1 d . . . . .
H5 H 0.700226 0.345842 0.268279 0.032 Uiso 1 1 calc R U . . .
C6 C 0.66419(12) 0.2972(2) 0.3885(2) 0.0201(6) Uani 1 1 d . . . . .
C7 C 0.70593(12) 0.3584(2) 0.4756(2) 0.0174(5) Uani 1 1 d . . . . .
C8 C 0.75262(13) 0.4207(2) 0.4563(2) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.759221 0.423737 0.387183 0.024 Uiso 1 1 calc R U . . .
C9 C 0.78888(12) 0.4777(2) 0.5394(2) 0.0198(6) Uani 1 1 d . . . . .
C10 C 0.83734(14) 0.5530(3) 0.5275(3) 0.0267(6) Uani 1 1 d . . . . .
H10A H 0.821513 0.626432 0.519868 0.040 Uiso 1 1 calc R U . . .
H10B H 0.850588 0.533608 0.464090 0.040 Uiso 1 1 calc R U . . .
H10C H 0.871752 0.548529 0.590674 0.040 Uiso 1 1 calc R U . . .
C11 C 0.73310(13) 0.4052(2) 0.6530(2) 0.0196(6) Uani 1 1 d . . . . .
C12 C 0.63826(13) 0.1656(2) 0.7164(2) 0.0196(5) Uani 1 1 d . . . . .
C17 C 0.57138(13) 0.4398(2) 0.6887(3) 0.0309(7) Uani 1 1 d D . . . .
H17 H 0.587130 0.509393 0.708909 0.037 Uiso 1 1 calc R U . . .
C16 C 0.51175(14) 0.4236(2) 0.6342(3) 0.0351(8) Uani 1 1 d D . . . .
C15 C 0.48908(14) 0.3206(2) 0.6035(3) 0.0338(8) Uani 1 1 d D . . . .
H15 H 0.447622 0.311035 0.567368 0.041 Uiso 1 1 calc R U . . .
C14 C 0.52714(13) 0.23358(16) 0.6260(2) 0.0264(6) Uani 1 1 d D . . . .
C13 C 0.58745(12) 0.2455(2) 0.6815(2) 0.0206(6) Uani 1 1 d . . . . .
C18 C 0.60720(13) 0.3481(2) 0.7124(2) 0.0229(6) Uani 1 1 d . . . . .
Br1B Br 0.4967(3) 0.0986(2) 0.5760(5) 0.0367(10) Uani 0.418(2) 1 d D . P A 2
Cl1B Cl 0.4696(3) 0.5412(3) 0.6106(7) 0.0359(10) Uani 0.418(2) 1 d D U P A 2


_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
Cl1A C14 1.729(2) . ?
Br1A C16 1.8745(18) . ?
S1 O1 1.436(2) . ?
S1 N1 1.588(3) . ?
S1 N2 1.565(2) . ?
S1 C18 1.774(3) . ?
O2 C12 1.232(4) . ?
N1 C12 1.353(4) . ?
N2 C11 1.351(4) . ?
N3 C7 1.351(4) . ?
N3 C11 1.334(4) . ?
N4 H4 0.8800 . ?
N4 C9 1.347(4) . ?
N4 C11 1.359(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(5) . ?
C4 H4A 0.9500 . ?
C4 C5 1.395(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(4) . ?
C6 C7 1.488(4) . ?
C7 C8 1.396(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(4) . ?
C9 C10 1.492(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.509(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.379(5) . ?
C17 C18 1.394(4) . ?
C16 C15 1.404(5) . ?
C16 Cl1B 1.738(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.374(4) . ?
C14 C13 1.389(4) . ?
C14 Br1B 1.8725(19) . ?
C13 C18 1.382(4) . ?

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 N1 113.95(14) . . ?
O1 S1 N2 108.43(13) . . ?
O1 S1 C18 109.69(15) . . ?
N1 S1 C18 97.54(13) . . ?
N2 S1 N1 113.54(14) . . ?
N2 S1 C18 113.43(14) . . ?
C12 N1 S1 111.77(19) . . ?
C11 N2 S1 121.3(2) . . ?
C11 N3 C7 118.0(2) . . ?
C9 N4 H4 118.9 . . ?
C9 N4 C11 122.2(2) . . ?
C11 N4 H4 118.9 . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4A 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 119.9(3) . . ?
C5 C6 C7 120.9(3) . . ?
N3 C7 C6 116.9(2) . . ?
N3 C7 C8 121.9(2) . . ?
C8 C7 C6 121.2(3) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.7 . . ?
N4 C9 C8 117.8(3) . . ?
N4 C9 C10 118.3(3) . . ?
C8 C9 C10 123.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 N4 113.4(2) . . ?
N3 C11 N2 125.2(3) . . ?
N3 C11 N4 121.3(3) . . ?
O2 C12 N1 122.9(3) . . ?
O2 C12 C13 124.0(3) . . ?
N1 C12 C13 113.0(2) . . ?
C16 C17 H17 122.0 . . ?
C16 C17 C18 116.1(3) . . ?
C18 C17 H17 122.0 . . ?
C17 C16 Br1A 120.1(3) . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 Cl1B 113.4(3) . . ?
C15 C16 Br1A 118.4(2) . . ?
C15 C16 Cl1B 125.1(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C15 C14 Cl1A 116.7(5) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 Br1B 118.6(3) . . ?
C13 C14 Cl1A 122.3(5) . . ?
C13 C14 Br1B 120.4(3) . . ?
C14 C13 C12 132.0(3) . . ?
C18 C13 C12 110.9(2) . . ?
C18 C13 C14 117.1(2) . . ?
C17 C18 S1 129.1(2) . . ?
C13 C18 S1 106.2(2) . . ?
C13 C18 C17 124.5(3) . . ?

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
Cl1A C14 C13 C12 1.2(7) . . . . ?
Cl1A C14 C13 C18 -179.0(6) . . . . ?
Br1A C16 C15 C14 178.6(3) . . . . ?
S1 N1 C12 O2 -175.6(2) . . . . ?
S1 N1 C12 C13 3.5(3) . . . . ?
S1 N2 C11 N3 6.7(4) . . . . ?
S1 N2 C11 N4 -175.4(2) . . . . ?
O1 S1 N1 C12 109.3(2) . . . . ?
O1 S1 N2 C11 -175.4(2) . . . . ?
O1 S1 C18 C17 64.5(3) . . . . ?
O1 S1 C18 C13 -111.5(2) . . . . ?
O2 C12 C13 C14 1.0(5) . . . . ?
O2 C12 C13 C18 -178.8(3) . . . . ?
N1 S1 N2 C11 56.9(3) . . . . ?
N1 S1 C18 C17 -176.7(3) . . . . ?
N1 S1 C18 C13 7.3(2) . . . . ?
N1 C12 C13 C14 -178.0(3) . . . . ?
N1 C12 C13 C18 2.2(3) . . . . ?
N2 S1 N1 C12 -125.9(2) . . . . ?
N2 S1 C18 C17 -56.9(3) . . . . ?
N2 S1 C18 C13 127.1(2) . . . . ?
N3 C7 C8 C9 -1.3(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C1 C6 C7 N3 -2.7(4) . . . . ?
C1 C6 C7 C8 177.6(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 178.5(3) . . . . ?
C5 C6 C7 N3 178.6(2) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
C6 C7 C8 C9 178.4(2) . . . . ?
C7 N3 C11 N2 178.8(3) . . . . ?
C7 N3 C11 N4 1.0(4) . . . . ?
C7 C8 C9 N4 2.2(4) . . . . ?
C7 C8 C9 C10 -175.5(3) . . . . ?
C9 N4 C11 N2 -178.1(2) . . . . ?
C9 N4 C11 N3 -0.1(4) . . . . ?
C11 N3 C7 C6 180.0(2) . . . . ?
C11 N3 C7 C8 -0.3(4) . . . . ?
C11 N4 C9 C8 -1.5(4) . . . . ?
C11 N4 C9 C10 176.3(3) . . . . ?
C12 C13 C18 S1 -6.0(3) . . . . ?
C12 C13 C18 C17 177.7(3) . . . . ?
C17 C16 C15 C14 -1.4(5) . . . . ?
C16 C17 C18 S1 -172.7(3) . . . . ?
C16 C17 C18 C13 2.7(5) . . . . ?
C16 C15 C14 Cl1A -179.3(6) . . . . ?
C16 C15 C14 C13 1.9(5) . . . . ?
C16 C15 C14 Br1B -176.0(4) . . . . ?
C15 C14 C13 C12 179.9(3) . . . . ?
C15 C14 C13 C18 -0.3(4) . . . . ?
C14 C13 C18 S1 174.1(2) . . . . ?
C14 C13 C18 C17 -2.1(5) . . . . ?
C18 S1 N1 C12 -6.2(2) . . . . ?
C18 S1 N2 C11 -53.2(3) . . . . ?
C18 C17 C16 Br1A 179.2(3) . . . . ?
C18 C17 C16 C15 -0.8(5) . . . . ?
C18 C17 C16 Cl1B 178.5(4) . . . . ?
Br1B C14 C13 C12 -2.2(5) . . . . ?
Br1B C14 C13 C18 177.6(4) . . . . ?
Cl1B C16 C15 C14 179.4(5) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_275
_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
;
####################################################################### 
# 
# 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_az14263847
_database_code_depnum_ccdc_archive 'CCDC 2517071'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-12-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 N4 O3 S'
_chemical_formula_sum            'C18 H18 N4 O3 S'
_chemical_formula_weight         370.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.21200(10)
_cell_length_b                   15.06670(10)
_cell_length_c                   10.57580(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.6200(10)
_cell_angle_gamma                90
_cell_volume                     1755.95(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14281
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7690
_cell_measurement_theta_min      2.9570
_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.654
_exptl_absorpt_coefficient_mu    1.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sort
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 0 0.0452
2 0 -5 0.0866
-1 -5 2 0.0501
1 5 -2 0.0501
-1 -5 0 0.0588
1 0 0 0.0586
-1 0 0 0.0727
-5 -1 -4 0.0881
-2 3 5 0.1342
-3 -5 1 0.0409
3 -5 3 0.0756
1 -5 1 0.0554

_exptl_crystal_preparation       
'The material was recrystallized from methanol by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.1
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0003 4.9973 0.0002 0.4671 0.2496 0.0092
2.0036 0.0021 -5.0049 0.0189 0.0162 0.7424
-1.0015 -4.9982 2.0017 -0.4990 -0.1487 -0.2863
1.0015 4.9982 -2.0017 0.4990 0.1487 0.2863
-1.0003 -4.9973 -0.0002 -0.4671 -0.2496 -0.0092
1.0003 0.0000 0.0000 -0.0304 0.1343 0.0248
-1.0003 -0.0000 -0.0000 0.0304 -0.1343 -0.0248
-4.9988 -0.9981 -4.0040 0.1163 -0.8963 0.4332
-2.0036 2.9963 5.0050 0.2795 0.0531 -0.7518
-3.0014 -4.9978 1.0007 -0.4222 -0.4677 -0.1975
2.9989 -4.9984 3.0027 -0.6365 0.4388 -0.3256
0.9996 -4.9977 1.0007 -0.5438 0.0693 -0.0981

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.292
_diffrn_reflns_theta_min         4.012
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  21.00   0.50    0.05    --   32.00  99.00  30.91   58
  2  ω     11.00  39.00   0.50    0.05    --   40.00  81.00-135.17   56
  3  ω     40.00 135.00   0.50    0.05    --   64.00  72.00-134.94  190
  4  ω     95.00 171.00   0.50    0.08    --   96.59 125.00 -90.00  152
  5  ω     95.00 171.00   0.50    0.08    --   96.59 125.00 -60.00  152
  6  ω     91.00 171.00   0.50    0.08    --   96.59 131.00  48.00  160
  7  ω     16.00  43.00   0.50    0.05    --   44.00  79.00 152.05   54
  8  ω    -96.00 -20.00   0.50    0.05    --  -51.38 139.00-136.00  152
  9  ω    -96.00 -20.00   0.50    0.08    --  -79.95 139.00-136.00  152
 10  ω   -120.00 -80.00   0.50    0.05    --  -51.38 -77.00-180.00   80
 11  ω   -120.00 -80.00   0.50    0.05    --  -51.38 -77.00  30.00   80
 12  ω   -142.00-117.00   0.50    0.05    --  -68.00 -62.00  61.37   50
 13  ω    -35.00   0.00   0.50    0.08    --  -79.95  30.00   0.00   70
 14  ω    -35.00   0.00   0.50    0.08    --  -79.95  30.00  90.00   70
 15  ω    -35.00   0.00   0.50    0.08    --  -79.95  30.00 -30.00   70
 16  ω    -35.00   0.00   0.50    0.08    --  -79.95  30.00-150.00   70
 17  ω   -125.00 -70.00   0.50    0.05    --  -51.38-131.00 -22.00  110
 18  ω   -124.00 -64.00   0.50    0.05    --  -51.38-139.00 162.00  120
 19  ω   -153.00 -64.00   0.50    0.08    --  -79.95-139.00 162.00  178
 20  ω   -154.00 -70.00   0.50    0.08    --  -79.95-131.00 -22.00  168
 21  ω     19.00  51.00   0.50    0.08    --   96.59 -45.00 -30.00   64
 22  ω     19.00  51.00   0.50    0.08    --   96.59 -45.00-150.00   64
 23  ω     19.00  51.00   0.50    0.08    --   96.59 -45.00-180.00   64
 24  ω     40.00 105.00   0.50    0.08    --  108.39 -77.00 150.00  130
 25  ω     44.00 125.00   0.50    0.08    --  102.49-143.00 152.54  162
 26  ω     42.00 122.00   0.50    0.08    --   96.59-139.00 162.00  160
 27  ω     42.00 122.00   0.50    0.08    --  108.39-139.00 162.00  160
 28  ω     42.00 115.00   0.50    0.05    --   50.95-139.00 162.00  146
 29  ω     38.00 116.00   0.50    0.08    --  108.39-131.00 -22.00  156
 30  ω     38.00 116.00   0.50    0.08    --   96.59-131.00 -22.00  156
 31  ω     28.00 105.00   0.50    0.08    --   96.59 -95.00 -30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0303975000
_diffrn_orient_matrix_UB_12      0.0995461000
_diffrn_orient_matrix_UB_13      -0.0159125000
_diffrn_orient_matrix_UB_21      0.1342233000
_diffrn_orient_matrix_UB_22      0.0230872000
_diffrn_orient_matrix_UB_23      0.0505145000
_diffrn_orient_matrix_UB_31      0.0248252000
_diffrn_orient_matrix_UB_32      -0.0031130000
_diffrn_orient_matrix_UB_33      -0.1384042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3397
_reflns_number_total             3579
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.302
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00176(16)
_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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.047
_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)+(0.0337P)²+0.9574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
;
_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 0.64345(3) 0.76846(2) 0.21753(3) 0.01463(10) Uani 1 1 d . . . . .
O1 O 0.63565(8) 0.77376(6) 0.08101(8) 0.0187(2) Uani 1 1 d . . . . .
O2 O 0.48970(8) 0.90962(6) 0.41098(9) 0.0196(2) Uani 1 1 d . . . . .
O3 O 0.22127(8) 0.61478(6) 0.38561(8) 0.0168(2) Uani 1 1 d . . . . .
N1 N 0.23043(11) 0.82151(8) 0.50223(12) 0.0253(3) Uani 1 1 d . . . . .
N2 N 0.62609(10) 0.85569(7) 0.29161(10) 0.0172(2) Uani 1 1 d . . . . .
N3 N 0.77882(10) 0.73237(7) 0.28299(10) 0.0182(2) Uani 1 1 d . . . . .
N4 N 0.73995(10) 0.60409(7) 0.16228(10) 0.0176(2) Uani 1 1 d . . . . .
C1 C 0.29326(12) 0.78356(9) 0.44688(12) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.36372(11) 0.72916(9) 0.37557(12) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.32423(11) 0.64173(9) 0.34571(11) 0.0153(3) Uani 1 1 d . . . . .
C4 C 0.38387(11) 0.58768(9) 0.26989(12) 0.0168(3) Uani 1 1 d . . . . .
H4 H 0.354896 0.529251 0.249150 0.020 Uiso 1 1 calc R U . . .
C5 C 0.48507(11) 0.61825(9) 0.22438(12) 0.0160(3) Uani 1 1 d . . . . .
H5 H 0.524869 0.582445 0.170942 0.019 Uiso 1 1 calc R U . . .
C6 C 0.52558(11) 0.70333(9) 0.26029(12) 0.0154(3) Uani 1 1 d . . . . .
C7 C 0.46739(11) 0.75918(9) 0.33315(11) 0.0152(3) Uani 1 1 d . . . . .
C8 C 0.52620(11) 0.84943(9) 0.35230(12) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.23225(11) 0.55833(9) 0.50259(12) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.22844(15) 0.46205(10) 0.46102(15) 0.0286(3) Uani 1 1 d . . . . .
H10A H 0.154447 0.451233 0.397524 0.043 Uiso 1 1 calc R U . . .
H10B H 0.228811 0.423762 0.535997 0.043 Uiso 1 1 calc R U . . .
H10C H 0.299598 0.448843 0.422625 0.043 Uiso 1 1 calc R U . . .
C11 C 0.12179(13) 0.58451(11) 0.55805(14) 0.0263(3) Uani 1 1 d . . . . .
H11A H 0.128538 0.646965 0.584299 0.039 Uiso 1 1 calc R U . . .
H11B H 0.117067 0.547290 0.632958 0.039 Uiso 1 1 calc R U . . .
H11C H 0.048412 0.576202 0.492723 0.039 Uiso 1 1 calc R U . . .
C12 C 0.34811(13) 0.57901(11) 0.59687(14) 0.0275(3) Uani 1 1 d . . . . .
H12A H 0.418338 0.563303 0.558326 0.041 Uiso 1 1 calc R U . . .
H12B H 0.350061 0.544584 0.675849 0.041 Uiso 1 1 calc R U . . .
H12C H 0.350792 0.642498 0.617344 0.041 Uiso 1 1 calc R U . . .
C13 C 0.85189(13) 0.77496(10) 0.39609(13) 0.0249(3) Uani 1 1 d . . . . .
H13A H 0.909043 0.816621 0.368288 0.037 Uiso 1 1 calc R U . . .
H13B H 0.897024 0.729573 0.451741 0.037 Uiso 1 1 calc R U . . .
H13C H 0.798419 0.807146 0.443774 0.037 Uiso 1 1 calc R U . . .
C14 C 0.82491(11) 0.65859(9) 0.22325(12) 0.0164(3) Uani 1 1 d . . . . .
C15 C 0.94888(12) 0.64617(10) 0.23026(12) 0.0199(3) Uani 1 1 d . . . . .
H15 H 1.006571 0.686920 0.274474 0.024 Uiso 1 1 calc R U . . .
C16 C 0.98444(12) 0.57172(10) 0.16988(12) 0.0219(3) Uani 1 1 d . . . . .
H16 H 1.068197 0.560252 0.172656 0.026 Uiso 1 1 calc R U . . .
C17 C 0.89784(12) 0.51395(9) 0.10543(12) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.921047 0.462566 0.063870 0.025 Uiso 1 1 calc R U . . .
C18 C 0.77636(12) 0.53307(9) 0.10313(12) 0.0190(3) Uani 1 1 d . . . . .
H18 H 0.716591 0.494246 0.057805 0.023 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 1.4326(9) . ?
S1 N2 1.5605(11) . ?
S1 N3 1.6406(11) . ?
S1 C6 1.7704(13) . ?
O2 C8 1.2119(16) . ?
O3 C3 1.3620(14) . ?
O3 C9 1.4876(15) . ?
N1 C1 1.1480(18) . ?
N2 C8 1.3928(16) . ?
N3 C13 1.4672(16) . ?
N3 C14 1.4220(17) . ?
N4 C14 1.3308(17) . ?
N4 C18 1.3405(17) . ?
C1 C2 1.4436(18) . ?
C2 C3 1.4069(18) . ?
C2 C7 1.3961(17) . ?
C3 C4 1.3968(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3900(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3894(18) . ?
C6 C7 1.3830(18) . ?
C7 C8 1.5084(18) . ?
C9 C10 1.5141(19) . ?
C9 C11 1.5169(18) . ?
C9 C12 1.5171(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3909(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3853(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.3880(18) . ?
C18 H18 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 N2 117.97(6) . . ?
O1 S1 N3 108.88(6) . . ?
O1 S1 C6 112.25(6) . . ?
N2 S1 N3 104.99(6) . . ?
N2 S1 C6 99.82(6) . . ?
N3 S1 C6 112.62(6) . . ?
C3 O3 C9 118.89(9) . . ?
C8 N2 S1 111.07(9) . . ?
C13 N3 S1 122.22(9) . . ?
C14 N3 S1 117.09(9) . . ?
C14 N3 C13 120.67(11) . . ?
C14 N4 C18 117.80(11) . . ?
N1 C1 C2 174.53(14) . . ?
C3 C2 C1 117.97(11) . . ?
C7 C2 C1 123.51(12) . . ?
C7 C2 C3 118.52(12) . . ?
O3 C3 C2 117.34(11) . . ?
O3 C3 C4 121.79(12) . . ?
C4 C3 C2 120.70(11) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.89(12) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.23(12) . . ?
C6 C5 H5 121.4 . . ?
C5 C6 S1 131.56(10) . . ?
C7 C6 S1 104.83(9) . . ?
C7 C6 C5 123.35(12) . . ?
C2 C7 C8 128.18(11) . . ?
C6 C7 C2 119.21(12) . . ?
C6 C7 C8 112.57(11) . . ?
O2 C8 N2 124.15(12) . . ?
O2 C8 C7 124.25(11) . . ?
N2 C8 C7 111.59(11) . . ?
O3 C9 C10 108.22(10) . . ?
O3 C9 C11 102.97(10) . . ?
O3 C9 C12 111.03(10) . . ?
C10 C9 C11 112.34(12) . . ?
C10 C9 C12 111.26(12) . . ?
C11 C9 C12 110.71(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 N3 114.29(11) . . ?
N4 C14 C15 124.18(12) . . ?
C15 C14 N3 121.52(12) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 117.00(12) . . ?
C16 C15 H15 121.5 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.01(12) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.33(13) . . ?
C18 C17 H17 120.8 . . ?
N4 C18 C17 122.66(12) . . ?
N4 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N2 C8 O2 -176.32(10) . . . . ?
S1 N2 C8 C7 2.31(13) . . . . ?
S1 N3 C14 N4 -28.79(15) . . . . ?
S1 N3 C14 C15 151.47(11) . . . . ?
S1 C6 C7 C2 175.93(9) . . . . ?
S1 C6 C7 C8 -2.06(12) . . . . ?
O1 S1 N2 C8 118.61(9) . . . . ?
O1 S1 N3 C13 133.00(11) . . . . ?
O1 S1 N3 C14 -45.36(11) . . . . ?
O1 S1 C6 C5 51.47(14) . . . . ?
O1 S1 C6 C7 -122.69(9) . . . . ?
O3 C3 C4 C5 176.49(11) . . . . ?
N2 S1 N3 C13 5.80(12) . . . . ?
N2 S1 N3 C14 -172.57(9) . . . . ?
N2 S1 C6 C5 177.27(12) . . . . ?
N2 S1 C6 C7 3.11(10) . . . . ?
N3 S1 N2 C8 -119.95(9) . . . . ?
N3 S1 C6 C5 -71.84(13) . . . . ?
N3 S1 C6 C7 114.00(9) . . . . ?
N3 C14 C15 C16 179.37(12) . . . . ?
N4 C14 C15 C16 -0.3(2) . . . . ?
C1 C2 C3 O3 0.49(17) . . . . ?
C1 C2 C3 C4 175.84(11) . . . . ?
C1 C2 C7 C6 -177.01(12) . . . . ?
C1 C2 C7 C8 0.6(2) . . . . ?
C2 C3 C4 C5 1.35(19) . . . . ?
C2 C7 C8 O2 0.9(2) . . . . ?
C2 C7 C8 N2 -177.70(12) . . . . ?
C3 O3 C9 C10 -91.71(13) . . . . ?
C3 O3 C9 C11 149.18(11) . . . . ?
C3 O3 C9 C12 30.66(16) . . . . ?
C3 C2 C7 C6 1.92(18) . . . . ?
C3 C2 C7 C8 179.56(11) . . . . ?
C3 C4 C5 C6 1.64(18) . . . . ?
C4 C5 C6 S1 -176.18(10) . . . . ?
C4 C5 C6 C7 -2.94(18) . . . . ?
C5 C6 C7 C2 1.16(19) . . . . ?
C5 C6 C7 C8 -176.84(11) . . . . ?
C6 S1 N2 C8 -3.18(10) . . . . ?
C6 S1 N3 C13 -101.83(12) . . . . ?
C6 S1 N3 C14 79.80(11) . . . . ?
C6 C7 C8 O2 178.69(12) . . . . ?
C6 C7 C8 N2 0.08(15) . . . . ?
C7 C2 C3 O3 -178.50(10) . . . . ?
C7 C2 C3 C4 -3.15(18) . . . . ?
C9 O3 C3 C2 -101.30(13) . . . . ?
C9 O3 C3 C4 83.41(14) . . . . ?
C13 N3 C14 N4 152.82(12) . . . . ?
C13 N3 C14 C15 -26.92(18) . . . . ?
C14 N4 C18 C17 1.22(19) . . . . ?
C14 C15 C16 C17 0.46(19) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 N4 -1.1(2) . . . . ?
C18 N4 C14 N3 179.78(11) . . . . ?
C18 N4 C14 C15 -0.50(19) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_273
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.818
####################################################################### 
# 
# 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_az14347289_100k
_database_code_depnum_ccdc_archive 'CCDC 2517073'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2023-01-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
okky.putra@astrazeneca.com
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N5 O3 S, 1.5(C2 H3 N)'
_chemical_formula_sum            'C23 H19.50 N6.50 O3 S'
_chemical_formula_weight         467.01
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.67280(10)
_cell_length_b                   17.10090(10)
_cell_length_c                   11.26990(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.6090(10)
_cell_angle_gamma                90
_cell_volume                     2327.93(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27381
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.1970
_cell_measurement_theta_min      4.1130
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.851
_exptl_absorpt_coefficient_mu    1.561
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             972
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0345
2 -2 -1 0.0463
-1 1 -1 0.0422
-1 1 1 0.0488
0 0 1 0.0476
4 5 0 0.0138
-4 -5 0 0.0207
-4 5 1 0.0494
4 -5 1 0.0567

_exptl_crystal_preparation       
'The material was recrystallized from acetonitrile by slow evaporation'
_exptl_crystal_recrystallization_method 
'The material was recrystallised from acetonitrile by slow evaporation'
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.034
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0001 -0.9994 0.1112 -0.0078 -0.0902
1.9990 -1.9983 -0.9997 -0.1388 0.0031 -0.2768
-0.9996 0.9993 -0.9993 0.2362 -0.0133 0.0032
-0.9995 0.9991 0.9996 0.0138 0.0023 0.1835
0.0000 -0.0001 0.9994 -0.1112 0.0078 0.0902
3.9974 4.9976 0.0002 -0.2335 -0.6386 0.0129
-3.9974 -4.9976 -0.0002 0.2335 0.6386 -0.0129
-3.9981 4.9961 1.0001 0.4185 -0.0875 0.5063
3.9982 -4.9963 0.9987 -0.6408 0.1031 -0.3260

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.332
_diffrn_reflns_theta_min         4.116
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  82.00   0.50    0.75    --   50.78 -84.00  52.00  198
  2  ω    -82.00  16.00   0.50    0.75    --  -51.28  84.00 171.00  196
  3  ω   -111.00 -12.00   0.50    1.67    --  -79.95  84.00 171.00  198
  4  ω   -148.00 -79.00   0.50    1.67    --  -79.95 -84.00  52.00  138
  5  ω    101.00 164.00   0.50    1.67    --   96.44  84.00 171.00  126
  6  ω     29.00 127.00   0.50    1.67    --   96.44 -84.00  52.00  196
  7  ω     41.00 139.00   0.50    1.67    --  108.37 -84.00  52.00  196
  8  ω     80.00 119.00   0.50    0.75    --   50.78  77.00 -90.00   78
  9  ω     80.00 119.00   0.50    0.75    --   50.78  77.00-150.00   78
 10  ω   -120.00 -80.00   0.50    0.75    --  -51.28 -77.00-180.00   80
 11  ω   -120.00 -80.00   0.50    0.75    --  -51.28 -77.00  30.00   80
 12  ω    -68.00  28.00   0.50    0.75    --  -51.28  38.00 120.00  192
 13  ω   -120.00 -80.00   0.50    0.75    --  -51.28 -77.00  90.00   80
 14  ω   -148.00 -80.00   0.50    1.67    --  -79.95 -77.00  90.00  136
 15  ω   -149.00 -86.00   0.50    1.67    --  -79.95 -95.00-180.00  126
 16  ω   -148.00 -80.00   0.50    1.67    --  -79.95 -77.00 120.00  136
 17  ω   -148.00 -80.00   0.50    1.67    --  -79.95 -77.00 -60.00  136
 18  ω   -149.00 -86.00   0.50    1.67    --  -79.95 -95.00   0.00  126
 19  ω     28.00 105.00   0.50    1.67    --   96.44 -95.00-150.00  154
 20  ω     76.00 176.00   0.50    1.67    --   96.44  30.00 -90.00  200
 21  ω     80.00 165.00   0.50    1.67    --   96.44  77.00  90.00  170
 22  ω     19.00 113.00   0.50    1.67    --   96.44 -45.00  30.00  188
 23  ω     95.00 171.00   0.50    1.67    --   96.44 125.00  30.00  152
 24  ω     34.00 112.00   0.50    1.67    --  108.37-125.00 -90.00  156
 25  ω     92.00 178.00   0.50    1.67    --  108.37  45.00 -60.00  172
 26  ω     88.00 178.00   0.50    1.67    --  108.37  30.00  90.00  180
 27  ω    101.00 176.00   0.50    1.67    --  108.37  84.00 171.00  150
 28  ω     31.00 126.00   0.50    0.75    --   50.78  57.00  30.00  190
 29  ω   -127.00 -32.00   0.50    0.75    --  -51.28 -57.00  30.00  190
 30  ω   -127.00 -32.00   0.50    0.75    --  -51.28 -57.00-180.00  190
 31  ω   -127.00 -32.00   0.50    0.75    --  -51.28 -57.00 -90.00  190
 32  ω    -85.00 -13.00   0.50    0.75    --  -51.28 125.00 -60.00  144
 33  ω   -127.00 -32.00   0.50    0.75    --  -51.28 -57.00  90.00  190
 34  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00-150.00  190
 35  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00  30.00  190
 36  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00 120.00  190
 37  ω   -154.00 -74.00   0.50    1.67    --  -79.95 -61.00  60.00  160
 38  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00-120.00  190
 39  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00   0.00  190
 40  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00 150.00  190
 41  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00 -60.00  190
 42  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00 -30.00  190
 43  ω   -154.00 -59.00   0.50    1.67    --  -79.95 -61.00-180.00  190
 44  ω     34.00 112.00   0.50    1.67    --   96.44-125.00  30.00  156
 45  ω     76.00 171.00   0.50    1.67    --   96.44  61.00   0.00  190
 46  ω     82.00 177.00   0.50    1.67    --  108.37  77.00 150.00  190
 47  ω     40.00 105.00   0.50    1.67    --  108.37 -95.00 -60.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0954507000
_diffrn_orient_matrix_UB_12      0.0296373000
_diffrn_orient_matrix_UB_13      -0.1112238000
_diffrn_orient_matrix_UB_21      -0.0679287000
_diffrn_orient_matrix_UB_22      -0.0734378000
_diffrn_orient_matrix_UB_23      0.0078288000
_diffrn_orient_matrix_UB_31      -0.0504341000
_diffrn_orient_matrix_UB_32      0.0429255000
_diffrn_orient_matrix_UB_33      0.0902118000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                4707
_reflns_number_total             4789
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.149
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2157 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4789
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.065
_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)+(0.0336P)²+1.2368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          
;
The absolute structure can be determined reliably from anomalous dispersion Flack parameter: 0.003(13) 
Hooft parameter: -0.014(2).
;
_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. Others
 Fixed Sof: H22A(0.5) H22B(0.5) H22C(0.5)
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46924(3) 0.48293(3) 0.70972(4) 0.01804(11) Uani 1 1 d . . . . .
O1 O 0.58735(10) 0.48958(10) 0.73501(12) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.27595(12) 0.37082(8) 0.46760(13) 0.0255(3) Uani 1 1 d . . . . .
O3 O 0.18051(12) 0.65978(8) 0.29946(13) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.41681(14) 0.40496(10) 0.64268(15) 0.0214(4) Uani 1 1 d . . . . .
N2 N 0.44937(12) 0.49476(10) 0.84165(14) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.34146(13) 0.50321(10) 0.97024(15) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.407(2) 0.5035(17) 1.035(3) 0.039(8) Uiso 1 1 d . . . . .
N4 N 0.25329(12) 0.49251(10) 0.75474(14) 0.0201(3) Uani 1 1 d . . . . .
N5 N 0.12010(13) 0.47579(11) 0.21283(16) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.33392(16) 0.42073(12) 0.53391(18) 0.0200(4) Uani 1 1 d . . . . .
C2 C 0.32178(15) 0.50712(11) 0.50664(17) 0.0174(4) Uani 1 1 d . . . . .
C3 C 0.39353(15) 0.55067(12) 0.59941(18) 0.0186(4) Uani 1 1 d . . . . .
C4 C 0.39628(16) 0.63127(12) 0.59966(18) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.446147 0.659223 0.666116 0.026 Uiso 1 1 calc R U . . .
C5 C 0.32399(17) 0.67033(12) 0.49988(18) 0.0218(4) Uani 1 1 d . . . . .
H5 H 0.322945 0.725868 0.498080 0.026 Uiso 1 1 calc R U . . .
C6 C 0.25252(15) 0.62782(12) 0.40174(17) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.25034(15) 0.54550(12) 0.40500(17) 0.0175(4) Uani 1 1 d . . . . .
C8 C 0.17751(15) 0.50463(11) 0.30059(18) 0.0186(4) Uani 1 1 d . . . . .
C9 C 0.34588(15) 0.49675(11) 0.85150(17) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.24416(17) 0.50694(13) 0.9956(2) 0.0240(4) Uani 1 1 d . . . . .
H10 H 0.242667 0.511193 1.079089 0.029 Uiso 1 1 calc R U . . .
C11 C 0.14799(16) 0.50452(13) 0.8997(2) 0.0263(4) Uani 1 1 d . . . . .
H11 H 0.077842 0.507437 0.913659 0.032 Uiso 1 1 calc R U . . .
C12 C 0.15751(15) 0.49754(12) 0.77988(18) 0.0230(4) Uani 1 1 d . . . . .
H12 H 0.091281 0.496312 0.711926 0.028 Uiso 1 1 calc R U . . .
C13 C 0.19112(16) 0.74248(12) 0.27240(19) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.187919 0.775066 0.344906 0.026 Uiso 1 1 calc R U . . .
C14 C 0.09026(17) 0.75845(13) 0.1616(2) 0.0275(4) Uani 1 1 d . . . . .
H14A H 0.095027 0.727596 0.090162 0.041 Uiso 1 1 calc R U . . .
H14B H 0.087431 0.814201 0.140758 0.041 Uiso 1 1 calc R U . . .
H14C H 0.023179 0.743884 0.182440 0.041 Uiso 1 1 calc R U . . .
C15 C 0.29914(17) 0.75702(12) 0.24471(19) 0.0239(4) Uani 1 1 d . . . . .
C16 C 0.32251(19) 0.71691(15) 0.1478(2) 0.0319(5) Uani 1 1 d . . . . .
H16 H 0.272287 0.678589 0.101911 0.038 Uiso 1 1 calc R U . . .
C17 C 0.4186(2) 0.73280(18) 0.1183(3) 0.0424(6) Uani 1 1 d . . . . .
H17 H 0.433916 0.705517 0.051987 0.051 Uiso 1 1 calc R U . . .
C18 C 0.4922(2) 0.78799(17) 0.1846(3) 0.0474(7) Uani 1 1 d . . . . .
H18 H 0.557272 0.799478 0.162763 0.057 Uiso 1 1 calc R U . . .
C19 C 0.4715(2) 0.82659(15) 0.2828(3) 0.0435(7) Uani 1 1 d . . . . .
H19 H 0.523323 0.863583 0.329925 0.052 Uiso 1 1 calc R U . . .
C20 C 0.37451(19) 0.81134(13) 0.3129(2) 0.0323(5) Uani 1 1 d . . . . .
H20 H 0.360107 0.838192 0.380153 0.039 Uiso 1 1 calc R U . . .
N6 N 0.000000 0.5743(2) 0.500000 0.0518(9) Uani 1 2 d S T P . .
C21 C 0.000000 0.6410(3) 0.500000 0.0389(8) Uani 1 2 d S T P . .
C22 C 0.000000 0.7256(3) 0.500000 0.0589(11) Uani 1 2 d S T P . .
H22A H 0.014371 0.744704 0.585413 0.088 Uiso 0.5 1 calc R U P A -1
H22B H -0.072250 0.744704 0.448499 0.088 Uiso 0.5 1 calc R U P A -1
H22C H 0.057880 0.744704 0.466088 0.088 Uiso 0.5 1 calc R U P A -1
N7 N 0.2505(2) 0.67381(14) 0.8245(3) 0.0514(6) Uani 1 1 d . . . . .
C23 C 0.2280(2) 0.73821(14) 0.8186(2) 0.0329(5) Uani 1 1 d . . . . .
C24 C 0.2025(2) 0.82112(15) 0.8129(3) 0.0443(6) Uani 1 1 d . . . . .
H24A H 0.233017 0.846453 0.752478 0.066 Uiso 1 1 calc R U . . .
H24B H 0.235296 0.844585 0.895204 0.066 Uiso 1 1 calc R U . . .
H24C H 0.122043 0.828310 0.787248 0.066 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 1.4410(13) . ?
S1 N1 1.5769(17) . ?
S1 N2 1.5942(15) . ?
S1 C3 1.757(2) . ?
O2 C1 1.222(2) . ?
O3 C6 1.350(2) . ?
O3 C13 1.461(2) . ?
N1 C1 1.378(2) . ?
N2 C9 1.350(2) . ?
N3 H3 0.93(3) . ?
N3 C9 1.361(2) . ?
N3 C10 1.349(2) . ?
N4 C9 1.341(2) . ?
N4 C12 1.330(2) . ?
N5 C8 1.147(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.378(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(3) . ?
C6 C7 1.409(3) . ?
C7 C8 1.438(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.363(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.396(3) . ?
C12 H12 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.517(3) . ?
C13 C15 1.514(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.396(3) . ?
C15 C20 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.395(3) . ?
C20 H20 0.9500 . ?
N6 C21 1.142(6) . ?
C21 C22 1.446(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N7 C23 1.134(3) . ?
C23 C24 1.451(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
O1 S1 N1 115.05(9) . . ?
O1 S1 N2 104.67(8) . . ?
O1 S1 C3 113.59(9) . . ?
N1 S1 N2 113.06(9) . . ?
N1 S1 C3 99.08(9) . . ?
N2 S1 C3 111.70(9) . . ?
C6 O3 C13 119.25(15) . . ?
C1 N1 S1 110.98(14) . . ?
C9 N2 S1 120.76(13) . . ?
C9 N3 H3 118.3(18) . . ?
C10 N3 H3 120.0(18) . . ?
C10 N3 C9 121.62(17) . . ?
C12 N4 C9 116.99(16) . . ?
O2 C1 N1 124.23(19) . . ?
O2 C1 C2 123.66(17) . . ?
N1 C1 C2 112.11(17) . . ?
C3 C2 C1 111.82(17) . . ?
C3 C2 C7 119.04(18) . . ?
C7 C2 C1 129.13(17) . . ?
C2 C3 S1 105.92(14) . . ?
C2 C3 C4 123.52(19) . . ?
C4 C3 S1 130.52(16) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.99(18) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.00(18) . . ?
C6 C5 H5 120.0 . . ?
O3 C6 C5 124.88(18) . . ?
O3 C6 C7 114.40(17) . . ?
C5 C6 C7 120.71(18) . . ?
C2 C7 C6 118.68(17) . . ?
C2 C7 C8 122.77(17) . . ?
C6 C7 C8 118.50(17) . . ?
N5 C8 C7 175.8(2) . . ?
N2 C9 N3 114.40(16) . . ?
N4 C9 N2 124.39(17) . . ?
N4 C9 N3 121.21(16) . . ?
N3 C10 H10 120.5 . . ?
N3 C10 C11 119.09(18) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.81(18) . . ?
C12 C11 H11 121.6 . . ?
N4 C12 C11 124.25(17) . . ?
N4 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
O3 C13 H13 109.9 . . ?
O3 C13 C14 103.78(16) . . ?
O3 C13 C15 110.37(16) . . ?
C14 C13 H13 109.9 . . ?
C15 C13 H13 109.9 . . ?
C15 C13 C14 112.96(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.0(2) . . ?
C20 C15 C13 120.7(2) . . ?
C20 C15 C16 119.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.0(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
N6 C21 C22 180.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N7 C23 C24 178.3(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 N1 C1 O2 -175.95(16) . . . . ?
S1 N1 C1 C2 3.3(2) . . . . ?
S1 N2 C9 N3 176.83(13) . . . . ?
S1 N2 C9 N4 -2.9(3) . . . . ?
S1 C3 C4 C5 -178.37(15) . . . . ?
O1 S1 N1 C1 -124.20(13) . . . . ?
O1 S1 N2 C9 176.03(15) . . . . ?
O1 S1 C3 C2 123.81(13) . . . . ?
O1 S1 C3 C4 -58.6(2) . . . . ?
O2 C1 C2 C3 176.88(18) . . . . ?
O2 C1 C2 C7 -2.8(3) . . . . ?
O3 C6 C7 C2 179.87(16) . . . . ?
O3 C6 C7 C8 2.4(2) . . . . ?
O3 C13 C15 C16 57.9(2) . . . . ?
O3 C13 C15 C20 -123.6(2) . . . . ?
N1 S1 N2 C9 -58.02(17) . . . . ?
N1 S1 C3 C2 1.29(14) . . . . ?
N1 S1 C3 C4 178.9(2) . . . . ?
N1 C1 C2 C3 -2.4(2) . . . . ?
N1 C1 C2 C7 177.96(18) . . . . ?
N2 S1 N1 C1 115.62(14) . . . . ?
N2 S1 C3 C2 -118.08(13) . . . . ?
N2 S1 C3 C4 59.5(2) . . . . ?
N3 C10 C11 C12 0.5(3) . . . . ?
C1 C2 C3 S1 0.44(19) . . . . ?
C1 C2 C3 C4 -177.39(18) . . . . ?
C1 C2 C7 C6 178.45(17) . . . . ?
C1 C2 C7 C8 -4.2(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 S1 N1 C1 -2.73(15) . . . . ?
C3 S1 N2 C9 52.71(17) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C3 C2 C7 C8 176.19(17) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 O3 -178.77(17) . . . . ?
C4 C5 C6 C7 2.2(3) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C5 C6 C7 C8 -178.48(17) . . . . ?
C6 O3 C13 C14 -173.83(16) . . . . ?
C6 O3 C13 C15 64.9(2) . . . . ?
C7 C2 C3 S1 -179.87(14) . . . . ?
C7 C2 C3 C4 2.3(3) . . . . ?
C9 N3 C10 C11 -0.3(3) . . . . ?
C9 N4 C12 C11 -2.0(3) . . . . ?
C10 N3 C9 N2 179.16(18) . . . . ?
C10 N3 C9 N4 -1.1(3) . . . . ?
C10 C11 C12 N4 0.6(3) . . . . ?
C12 N4 C9 N2 -178.12(18) . . . . ?
C12 N4 C9 N3 2.2(3) . . . . ?
C13 O3 C6 C5 13.9(3) . . . . ?
C13 O3 C6 C7 -167.04(16) . . . . ?
C13 C15 C16 C17 176.9(2) . . . . ?
C13 C15 C20 C19 -177.2(2) . . . . ?
C14 C13 C15 C16 -57.8(3) . . . . ?
C14 C13 C15 C20 120.7(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C15 C20 C19 1.3(3) . . . . ?
C16 C17 C18 C19 1.4(4) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
C18 C19 C20 C15 0.4(3) . . . . ?
C20 C15 C16 C17 -1.6(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_293
_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 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.803
####################################################################### 
# 
# 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_az14336264_100k
_database_code_depnum_ccdc_archive 'CCDC 2517070'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;AstraZeneca
Sweden
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
okky.putra@astrazeneca.com
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Br F3 N4 O2 S, C2 H6 O S'
_chemical_formula_sum            'C21 H18 Br F3 N4 O3 S2'
_chemical_formula_weight         575.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S F Br'
_chemical_oxdiff_usercomment     Mario
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3840(2)
_cell_length_b                   10.3587(2)
_cell_length_c                   13.1433(2)
_cell_angle_alpha                102.060(2)
_cell_angle_beta                 110.539(2)
_cell_angle_gamma                100.632(2)
_cell_volume                     1122.67(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17524
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.8050
_cell_measurement_theta_min      3.7600
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.302
_exptl_absorpt_coefficient_mu    4.763
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.46a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             580
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 -5 0.1328
-2 0 5 0.1018
-1 -2 5 0.1082
1 0 0 0.0313
-1 0 0 0.0010
0 -1 1 0.1153
2 -5 -1 0.1033
2 0 -5 0.0835
-2 5 3 0.2180

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DMSO by slow evaporation'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9920 5.0036 -5.0013 -0.2226 0.4053 -0.7438
-1.9973 -0.0028 5.0022 0.1468 -0.5896 0.0088
-0.9954 -2.0033 5.0018 0.0681 -0.5244 0.3103
0.9995 -0.0002 0.0000 -0.1816 -0.0143 0.0125
-0.9995 0.0002 -0.0000 0.1816 0.0143 -0.0125
0.0015 -1.0008 1.0003 0.0082 -0.0839 0.1513
2.0045 -5.0003 -1.0013 -0.0626 0.2936 0.7408
1.9973 0.0028 -5.0022 -0.1468 0.5896 -0.0088
-2.0038 4.9990 3.0022 -0.0240 -0.5409 -0.7273

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28752
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.686
_diffrn_reflns_theta_min         3.762
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00 117.00   0.50    0.17    --   96.59 -61.00   0.00  190
  2  ω     22.00 117.00   0.50    0.17    --   96.59 -61.00 120.00  190
  3  ω     17.00  43.00   0.50    0.05    --   44.00  78.00 -67.33   52
  4  ω     17.00  43.00   0.50    0.05    --   44.00  78.00-112.29   52
  5  ω     31.00 125.00   0.50    0.17    --  108.39 -45.00-180.00  188
  6  ω     16.00  43.00   0.50    0.05    --   44.00  79.00-150.62   54
  7  ω    -99.00 -22.00   0.50    0.05    --  -50.82 142.00 -81.00  154
  8  ω    -88.00 -14.00   0.50    0.17    --  -79.95 128.00 107.00  148
  9  ω    -88.00 -14.00   0.50    0.05    --  -50.82 128.00 107.00  148
 10  ω     -1.00  25.00   0.50    0.05    --   36.00  94.00  30.63   52
 11  ω    -12.00  26.00   0.50    0.05    --   24.00  93.00 -93.53   76
 12  ω      0.00  26.00   0.50    0.05    --   36.00  93.00 120.67   52
 13  ω     10.00  37.00   0.50    0.05    --   40.00  83.00 147.29   54
 14  ω     80.00 119.00   0.50    0.05    --   50.20  77.00  60.00   78
 15  ω     82.00 177.00   0.50    0.17    --  108.39  77.00-180.00  190
 16  ω     37.00 131.00   0.50    0.05    --   60.00  71.00 -80.31  188
 17  ω     36.00 131.00   0.50    0.05    --   60.00  72.00  10.25  190
 18  ω     92.00 178.00   0.50    0.17    --  108.39  45.00 120.00  172
 19  ω     76.00 176.00   0.50    0.17    --   96.59  30.00 150.00  200
 20  ω     93.00 171.00   0.50    0.17    --   96.59 128.00 107.00  156
 21  ω     93.00 178.00   0.50    0.17    --  108.39 128.00 107.00  170
 22  ω     95.00 171.00   0.50    0.17    --   96.59 125.00  60.00  152
 23  ω     44.00 125.00   0.50    0.17    --  108.39-142.00-137.00  162
 24  ω     44.00 124.00   0.50    0.17    --   96.59-142.00-137.00  160
 25  ω     44.00 116.00   0.50    0.05    --   50.20-142.00-137.00  144
 26  ω     20.00 108.00   0.50    0.17    --   84.00-107.00 -55.77  176
 27  ω     36.00 108.00   0.50    0.05    --   50.20-128.00  33.00  144
 28  ω     36.00 114.00   0.50    0.17    --   96.59-128.00  33.00  156
 29  ω     36.00 113.00   0.50    0.17    --  108.39-128.00  33.00  154
 30  ω     40.00 105.00   0.50    0.17    --  108.39 -95.00  90.00  130
 31  ω     40.00 105.00   0.50    0.17    --  108.39 -95.00  30.00  130
 32  ω     40.00 105.00   0.50    0.17    --  108.39 -95.00-120.00  130
 33  ω   -159.00 -64.00   0.50    0.17    --  -88.00 -71.00  46.47  190
 34  ω   -139.00 -45.00   0.50    0.05    --  -68.00 -70.00 159.17  188
 35  ω   -135.00 -41.00   0.50    0.05    --  -64.00 -70.00  60.20  188
 36  ω   -152.00 -57.00   0.50    0.17    --  -80.00 -68.00 132.71  190
 37  ω   -160.00 -65.00   0.50    0.17    --  -88.50 -70.00  -5.77  190
 38  ω   -162.00 -67.00   0.50    0.17    --  -88.50 -65.00  98.68  190
 39  ω   -162.00 -67.00   0.50    0.17    --  -88.50 -63.00 -42.03  190
 40  ω   -161.00 -66.00   0.50    0.17    --  -88.50 -67.00 -89.18  190
 41  ω   -144.00 -49.00   0.50    0.17    --  -72.00 -69.00-148.45  190
 42  ω   -160.00-116.00   0.50    0.17    --  -88.50 -69.00-126.07   88
 43  ω   -149.00 -86.00   0.50    0.17    --  -79.95 -95.00 -90.00  126
 44  ω   -123.00 -62.00   0.50    0.05    --  -50.82-142.00-137.00  122
 45  ω   -152.00 -62.00   0.50    0.17    --  -79.95-142.00-137.00  180
 46  ω   -154.00 -72.00   0.50    0.17    --  -79.95-128.00  33.00  164
 47  ω   -125.00 -72.00   0.50    0.05    --  -50.82-128.00  33.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1817150000
_diffrn_orient_matrix_UB_12      -0.0516699000
_diffrn_orient_matrix_UB_13      -0.0432352000
_diffrn_orient_matrix_UB_21      -0.0142744000
_diffrn_orient_matrix_UB_22      -0.0396976000
_diffrn_orient_matrix_UB_23      -0.1235849000
_diffrn_orient_matrix_UB_31      0.0124879000
_diffrn_orient_matrix_UB_32      -0.1444747000
_diffrn_orient_matrix_UB_33      0.0066575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4157
_reflns_number_total             4614
_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 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.46a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.46a (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         0.901
_refine_diff_density_min         -1.168
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.074
_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)+(0.0707P)²+1.8769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1235
_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(H8), C1(H1), C15(H15), C17(H17), C4(H4), C5(H5), C2(H2A), C3(H3)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C10(H10A,H10B,H10C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37948(4) 0.82864(3) -0.03942(3) 0.02527(13) Uani 1 1 d . . . . .
S1 S 0.70416(8) 0.69718(7) 0.33482(6) 0.01857(17) Uani 1 1 d . . . . .
S2 S 0.19529(8) 0.48440(8) 0.35978(6) 0.02163(17) Uani 1 1 d . . . . .
F3 F 0.1564(2) 0.28609(19) -0.12177(16) 0.0300(4) Uani 1 1 d . . . . .
F1 F 0.0618(3) 0.3307(2) 0.0032(2) 0.0457(6) Uani 1 1 d . . . . .
O1 O 0.6653(2) 0.9707(2) 0.20282(18) 0.0225(4) Uani 1 1 d . . . . .
O3 O 0.2753(3) 0.3878(2) 0.31288(19) 0.0254(5) Uani 1 1 d . . . . .
O2 O 0.8219(3) 0.6240(2) 0.33759(19) 0.0254(5) Uani 1 1 d . . . . .
F2 F 0.2479(3) 0.2307(2) 0.0319(2) 0.0481(6) Uani 1 1 d . . . . .
N2 N 0.5356(3) 0.7318(3) 0.5553(2) 0.0190(5) Uani 1 1 d . . . . .
N1 N 0.4610(3) 0.8017(3) 0.3899(2) 0.0180(5) Uani 1 1 d . . . . .
N3 N 0.6607(3) 0.6849(3) 0.4386(2) 0.0206(5) Uani 1 1 d . . . . .
N4 N 0.7495(3) 0.8486(3) 0.3288(2) 0.0207(5) Uani 1 1 d . . . . .
C6 C 0.2602(3) 0.9198(3) 0.3428(3) 0.0193(6) Uani 1 1 d . . . . .
C9 C 0.4301(4) 0.7811(3) 0.5878(3) 0.0201(6) Uani 1 1 d . . . . .
C8 C 0.3405(3) 0.8479(3) 0.5220(3) 0.0199(6) Uani 1 1 d . . . . .
H8 H 0.268722 0.888200 0.544183 0.024 Uiso 1 1 calc R U . . .
C7 C 0.3574(3) 0.8552(3) 0.4212(3) 0.0189(6) Uani 1 1 d . . . . .
C11 C 0.5513(3) 0.7425(3) 0.4577(2) 0.0181(6) Uani 1 1 d . . . . .
C13 C 0.5274(3) 0.7299(3) 0.1507(3) 0.0185(6) Uani 1 1 d . . . . .
C18 C 0.4094(4) 0.6981(3) 0.0416(3) 0.0194(6) Uani 1 1 d . . . . .
C1 C 0.1392(4) 0.9683(3) 0.3611(3) 0.0220(6) Uani 1 1 d . . . . .
H1 H 0.117950 0.960407 0.425402 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6543(3) 0.8631(3) 0.2282(3) 0.0192(6) Uani 1 1 d . . . . .
C15 C 0.4350(4) 0.4954(3) 0.1553(3) 0.0205(6) Uani 1 1 d . . . . .
H15 H 0.443788 0.428439 0.195032 0.025 Uiso 1 1 calc R U . . .
C17 C 0.3065(4) 0.5662(3) -0.0106(3) 0.0210(6) Uani 1 1 d . . . . .
H17 H 0.227556 0.543668 -0.085553 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5375(3) 0.6265(3) 0.2026(2) 0.0189(6) Uani 1 1 d . . . . .
C4 C 0.1996(4) 0.9922(3) 0.1719(3) 0.0265(7) Uani 1 1 d . . . . .
H4 H 0.219619 0.999733 0.107051 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1957(4) 0.3268(4) -0.0106(3) 0.0255(7) Uani 1 1 d . . . . .
C16 C 0.3182(4) 0.4661(3) 0.0465(3) 0.0204(6) Uani 1 1 d . . . . .
C5 C 0.2891(4) 0.9324(3) 0.2472(3) 0.0229(6) Uani 1 1 d . . . . .
H5 H 0.370880 0.899732 0.233716 0.027 Uiso 1 1 calc R U . . .
C20 C 0.1023(4) 0.5491(3) 0.2458(3) 0.0269(7) Uani 1 1 d . . . . .
H20A H 0.183523 0.610144 0.233351 0.040 Uiso 1 1 calc R U . . .
H20B H 0.032736 0.600545 0.264901 0.040 Uiso 1 1 calc R U . . .
H20C H 0.039377 0.472203 0.176339 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4151(4) 0.7556(3) 0.6914(3) 0.0246(6) Uani 1 1 d . . . . .
H10A H 0.358494 0.658801 0.673697 0.037 Uiso 1 1 calc R U . . .
H10B H 0.355851 0.814370 0.716717 0.037 Uiso 1 1 calc R U . . .
H10C H 0.520919 0.776716 0.751963 0.037 Uiso 1 1 calc R U . . .
C2 C 0.0499(4) 1.0278(3) 0.2858(3) 0.0264(7) Uani 1 1 d . . . . .
H2A H -0.032801 1.059839 0.298583 0.032 Uiso 1 1 calc R U . . .
C3 C 0.0806(4) 1.0409(3) 0.1922(3) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.020192 1.083248 0.141798 0.031 Uiso 1 1 calc R U . . .
C21 C 0.0195(4) 0.3792(4) 0.3580(3) 0.0295(7) Uani 1 1 d . . . . .
H21A H -0.039381 0.310196 0.283245 0.044 Uiso 1 1 calc R U . . .
H21B H -0.047097 0.436908 0.372728 0.044 Uiso 1 1 calc R U . . .
H21C H 0.048768 0.332842 0.416882 0.044 Uiso 1 1 calc R U . . .
H2 H 0.589(6) 0.691(5) 0.594(4) 0.041(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.890(3) . ?
S1 O2 1.446(2) . ?
S1 N3 1.577(2) . ?
S1 N4 1.574(3) . ?
S1 C14 1.772(3) . ?
S2 O3 1.513(2) . ?
S2 C20 1.782(3) . ?
S2 C21 1.791(3) . ?
F3 C19 1.326(4) . ?
F1 C19 1.337(4) . ?
O1 C12 1.225(4) . ?
F2 C19 1.328(4) . ?
N2 C9 1.348(4) . ?
N2 C11 1.365(4) . ?
N2 H2 0.82(5) . ?
N1 C7 1.343(4) . ?
N1 C11 1.334(4) . ?
N3 C11 1.348(4) . ?
N4 C12 1.368(4) . ?
C6 C7 1.481(4) . ?
C6 C1 1.396(4) . ?
C6 C5 1.401(4) . ?
C9 C8 1.375(4) . ?
C9 C10 1.488(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.404(4) . ?
C13 C18 1.395(4) . ?
C13 C12 1.522(4) . ?
C13 C14 1.386(4) . ?
C18 C17 1.388(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.379(4) . ?
C15 C16 1.391(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.400(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(4) . ?
C4 C3 1.391(5) . ?
C19 C16 1.516(4) . ?
C5 H5 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C2 H2A 0.9500 . ?
C2 C3 1.385(5) . ?
C3 H3 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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 N3 106.37(13) . . ?
O2 S1 N4 115.55(14) . . ?
O2 S1 C14 110.14(14) . . ?
N3 S1 C14 112.49(14) . . ?
N4 S1 N3 114.20(14) . . ?
N4 S1 C14 98.08(14) . . ?
O3 S2 C20 104.55(14) . . ?
O3 S2 C21 106.79(15) . . ?
C20 S2 C21 97.90(16) . . ?
C9 N2 C11 121.9(3) . . ?
C9 N2 H2 119(3) . . ?
C11 N2 H2 119(3) . . ?
C11 N1 C7 118.8(3) . . ?
C11 N3 S1 120.2(2) . . ?
C12 N4 S1 112.3(2) . . ?
C1 C6 C7 121.8(3) . . ?
C1 C6 C5 118.6(3) . . ?
C5 C6 C7 119.5(3) . . ?
N2 C9 C8 118.3(3) . . ?
N2 C9 C10 117.5(3) . . ?
C8 C9 C10 124.2(3) . . ?
C9 C8 H8 120.8 . . ?
C9 C8 C7 118.4(3) . . ?
C7 C8 H8 120.8 . . ?
N1 C7 C6 116.6(3) . . ?
N1 C7 C8 121.6(3) . . ?
C8 C7 C6 121.9(3) . . ?
N1 C11 N2 120.9(3) . . ?
N1 C11 N3 125.9(3) . . ?
N3 C11 N2 113.2(3) . . ?
C18 C13 C12 131.3(3) . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C12 110.7(3) . . ?
C13 C18 Br1 122.8(2) . . ?
C17 C18 Br1 117.6(2) . . ?
C17 C18 C13 119.6(3) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
O1 C12 N4 124.9(3) . . ?
O1 C12 C13 122.8(3) . . ?
N4 C12 C13 112.2(3) . . ?
C14 C15 H15 121.7 . . ?
C14 C15 C16 116.6(3) . . ?
C16 C15 H15 121.7 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C13 C14 S1 106.5(2) . . ?
C15 C14 S1 129.1(2) . . ?
C15 C14 C13 124.3(3) . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
F3 C19 F1 106.6(3) . . ?
F3 C19 F2 107.8(3) . . ?
F3 C19 C16 111.8(2) . . ?
F1 C19 C16 111.1(3) . . ?
F2 C19 F1 107.7(3) . . ?
F2 C19 C16 111.6(3) . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 C19 120.5(3) . . ?
C17 C16 C19 118.5(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
S2 C20 H20A 109.5 . . ?
S2 C20 H20B 109.5 . . ?
S2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21B 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Br1 C18 C17 C16 -177.5(2) . . . . ?
S1 N3 C11 N2 -175.4(2) . . . . ?
S1 N3 C11 N1 6.4(4) . . . . ?
S1 N4 C12 O1 179.9(2) . . . . ?
S1 N4 C12 C13 1.5(3) . . . . ?
F3 C19 C16 C15 -144.6(3) . . . . ?
F3 C19 C16 C17 38.3(4) . . . . ?
F1 C19 C16 C15 96.4(3) . . . . ?
F1 C19 C16 C17 -80.7(3) . . . . ?
O2 S1 N3 C11 -179.3(2) . . . . ?
O2 S1 N4 C12 113.9(2) . . . . ?
O2 S1 C14 C13 -117.3(2) . . . . ?
O2 S1 C14 C15 61.9(3) . . . . ?
F2 C19 C16 C15 -23.8(4) . . . . ?
F2 C19 C16 C17 159.1(3) . . . . ?
N2 C9 C8 C7 3.2(4) . . . . ?
N3 S1 N4 C12 -122.2(2) . . . . ?
N3 S1 C14 C13 124.2(2) . . . . ?
N3 S1 C14 C15 -56.6(3) . . . . ?
N4 S1 N3 C11 52.0(3) . . . . ?
N4 S1 C14 C13 3.7(2) . . . . ?
N4 S1 C14 C15 -177.1(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C9 N2 C11 N1 -0.6(4) . . . . ?
C9 N2 C11 N3 -178.8(3) . . . . ?
C9 C8 C7 N1 -1.6(4) . . . . ?
C9 C8 C7 C6 177.2(3) . . . . ?
C7 N1 C11 N2 2.2(4) . . . . ?
C7 N1 C11 N3 -179.7(3) . . . . ?
C7 C6 C1 C2 -179.8(3) . . . . ?
C7 C6 C5 C4 179.8(3) . . . . ?
C11 N2 C9 C8 -2.2(4) . . . . ?
C11 N2 C9 C10 175.9(3) . . . . ?
C11 N1 C7 C6 180.0(3) . . . . ?
C11 N1 C7 C8 -1.1(4) . . . . ?
C13 C18 C17 C16 1.4(4) . . . . ?
C18 C13 C12 O1 3.0(5) . . . . ?
C18 C13 C12 N4 -178.6(3) . . . . ?
C18 C13 C14 S1 176.8(2) . . . . ?
C18 C13 C14 C15 -2.5(4) . . . . ?
C18 C17 C16 C15 -1.5(4) . . . . ?
C18 C17 C16 C19 175.5(3) . . . . ?
C1 C6 C7 N1 174.4(3) . . . . ?
C1 C6 C7 C8 -4.5(4) . . . . ?
C1 C6 C5 C4 0.1(5) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C12 C13 C18 Br1 -0.7(4) . . . . ?
C12 C13 C18 C17 -179.6(3) . . . . ?
C12 C13 C14 S1 -3.2(3) . . . . ?
C12 C13 C14 C15 177.6(3) . . . . ?
C14 S1 N3 C11 -58.6(3) . . . . ?
C14 S1 N4 C12 -3.0(2) . . . . ?
C14 C13 C18 Br1 179.3(2) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C14 C13 C12 O1 -177.1(3) . . . . ?
C14 C13 C12 N4 1.3(3) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C14 C15 C16 C19 -177.3(3) . . . . ?
C16 C15 C14 S1 -176.7(2) . . . . ?
C16 C15 C14 C13 2.4(4) . . . . ?
C5 C6 C7 N1 -5.3(4) . . . . ?
C5 C6 C7 C8 175.8(3) . . . . ?
C5 C6 C1 C2 -0.1(5) . . . . ?
C5 C4 C3 C2 -1.0(5) . . . . ?
C10 C9 C8 C7 -174.8(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id PSX_58
_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 2.782
_oxdiff_exptl_absorpt_empirical_full_min 0.664
