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

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

data_ZV2050
_database_code_depnum_ccdc_archive 'CCDC 2495035'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 D6 N O6 S'
_chemical_formula_weight         461.55

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5687(2)
_cell_length_b                   13.3383(4)
_cell_length_c                   13.7786(4)
_cell_angle_alpha                61.374(1)
_cell_angle_beta                 86.879(2)
_cell_angle_gamma                86.332(1)
_cell_volume                     1057.09(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7603
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      30.15

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18048
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.175
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6156
_reflns_number_gt                5256
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.3450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6156
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.80195(5) 1.08691(2) 0.00255(2) 0.01840(8) Uani 1 1 d . . . . .
O1 O 0.70927(12) 0.62700(8) 0.31226(8) 0.01940(18) Uani 1 1 d . . . . .
O2 O 0.56945(13) 0.88553(8) 0.22821(7) 0.01836(17) Uani 1 1 d . . . . .
O3 O 0.84419(13) 0.91855(8) 0.29654(7) 0.01778(17) Uani 1 1 d . . . . .
H3 H 0.853(3) 0.9791(19) 0.2269(19) 0.048(6) Uiso 1 1 d . . . . .
O4 O 0.22605(14) 0.38452(8) 0.08484(7) 0.01950(18) Uani 1 1 d . . . . .
O5 O 0.28984(12) 0.79561(7) 0.64139(7) 0.01583(16) Uani 1 1 d . . . . .
O6 O 0.88732(14) 1.09263(8) 0.09972(7) 0.02060(18) Uani 1 1 d . . . . .
N2 N 0.35942(14) 0.60028(8) 0.33644(8) 0.01255(18) Uani 1 1 d . . . . .
C1 C 0.54182(16) 0.63608(9) 0.35151(9) 0.0130(2) Uani 1 1 d . . . . .
C3 C 0.19068(16) 0.61946(10) 0.40247(9) 0.0136(2) Uani 1 1 d . . . . .
H3A H 0.167626 0.549564 0.473677 0.016 Uiso 1 1 calc R U . . .
H3B H 0.062255 0.644267 0.361255 0.016 Uiso 1 1 calc R U . . .
C3A C 0.26932(16) 0.71417(9) 0.42044(9) 0.01219(19) Uani 1 1 d . . . . .
H3AA H 0.246962 0.789233 0.352376 0.015 Uiso 1 1 calc R U . . .
C4 C 0.19375(17) 0.72508(10) 0.51987(9) 0.0146(2) Uani 1 1 d . . . . .
H4A H 0.069974 0.694478 0.559041 0.018 Uiso 1 1 calc R U . . .
C4A C 0.31724(17) 0.78183(10) 0.54774(9) 0.0136(2) Uani 1 1 d . . . . .
C5A C 0.47053(17) 0.83596(9) 0.65426(9) 0.0133(2) Uani 1 1 d . . . . .
C6 C 0.50780(18) 0.85230(10) 0.74310(9) 0.0157(2) Uani 1 1 d . . . . .
H6A H 0.408514 0.837531 0.800598 0.019 Uiso 1 1 calc R U . . .
C7 C 0.69899(18) 0.89168(10) 0.74410(10) 0.0166(2) Uani 1 1 d . . . . .
H7A H 0.731043 0.904343 0.803664 0.020 Uiso 1 1 calc R U . . .
C8 C 0.84382(18) 0.91280(10) 0.65960(10) 0.0165(2) Uani 1 1 d . . . . .
H8A H 0.973822 0.938107 0.663113 0.020 Uiso 1 1 calc R U . . .
C9 C 0.80003(17) 0.89716(10) 0.56939(9) 0.0148(2) Uani 1 1 d . . . . .
H9A H 0.897997 0.912605 0.511174 0.018 Uiso 1 1 calc R U . . .
C9A C 0.61059(17) 0.85867(9) 0.56735(9) 0.0127(2) Uani 1 1 d . . . . .
C9B C 0.50700(16) 0.84038(9) 0.48232(9) 0.01216(19) Uani 1 1 d . . . . .
H9BA H 0.461712 0.917442 0.422521 0.015 Uiso 1 1 calc R U . . .
C10 C 0.62803(16) 0.77667(9) 0.42456(9) 0.01129(19) Uani 1 1 d . . . . .
H10A H 0.758448 0.741827 0.463704 0.014 Uiso 1 1 calc R U . . .
C10A C 0.49819(16) 0.68252(9) 0.43181(9) 0.01173(19) Uani 1 1 d . . . . .
H10B H 0.516119 0.616381 0.507600 0.014 Uiso 1 1 calc R U . . .
C11 C 0.67618(17) 0.86454(9) 0.30557(9) 0.0128(2) Uani 1 1 d . . . . .
C12 C 0.32975(16) 0.54015(9) 0.27688(9) 0.0129(2) Uani 1 1 d . . . . .
C13 C 0.48468(18) 0.52467(11) 0.21030(10) 0.0174(2) Uani 1 1 d . . . . .
H13A H 0.617121 0.550998 0.207160 0.021 Uiso 1 1 calc R U . . .
C14 C 0.44418(18) 0.47099(11) 0.14924(10) 0.0187(2) Uani 1 1 d . . . . .
H14A H 0.549953 0.460678 0.104590 0.022 Uiso 1 1 calc R U . . .
C15 C 0.25078(18) 0.43172(10) 0.15206(9) 0.0157(2) Uani 1 1 d . . . . .
C16 C 0.09840(18) 0.44436(10) 0.21959(10) 0.0166(2) Uani 1 1 d . . . . .
H16A H -0.033050 0.416507 0.223662 0.020 Uiso 1 1 calc R U . . .
C17 C 0.13865(17) 0.49811(10) 0.28154(10) 0.0153(2) Uani 1 1 d . . . . .
H17A H 0.033636 0.506193 0.327814 0.018 Uiso 1 1 calc R U . . .
C18 C 0.0289(2) 0.34318(11) 0.08717(11) 0.0220(2) Uani 1 1 d . . . . .
H18A H 0.029676 0.311506 0.035996 0.033 Uiso 1 1 calc R U . . .
H18B H -0.004101 0.283430 0.162273 0.033 Uiso 1 1 calc R U . . .
H18C H -0.073788 0.406317 0.064832 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5561(2) 1.15734(14) -0.02006(12) 0.0276(3) Uani 1 1 d . . . . .
D19A D 0.494302 1.155879 -0.082496 0.041 Uiso 1 1 calc R U . . .
D19B D 0.469492 1.118121 0.046512 0.041 Uiso 1 1 calc R U . . .
D19C D 0.569204 1.236808 -0.036663 0.041 Uiso 1 1 calc R U . . .
C20 C 0.9322(2) 1.19191(12) -0.11647(10) 0.0255(3) Uani 1 1 d . . . . .
D20A D 0.883989 1.192870 -0.182985 0.038 Uiso 1 1 calc R U . . .
D20B D 0.904925 1.267298 -0.121421 0.038 Uiso 1 1 calc R U . . .
D20C D 1.079289 1.173241 -0.110373 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
S1 O6 1.5159(9) . ?
S1 C19 1.7797(15) . ?
S1 C20 1.7841(13) . ?
O1 C1 1.2239(13) . ?
O2 C11 1.2151(14) . ?
O3 C11 1.3241(13) . ?
O3 H3 0.91(2) . ?
O4 C15 1.3670(13) . ?
O4 C18 1.4326(15) . ?
O5 C5A 1.3877(13) . ?
O5 C4A 1.3889(13) . ?
N2 C1 1.3791(14) . ?
N2 C12 1.4223(14) . ?
N2 C3 1.4828(14) . ?
C1 C10A 1.5131(15) . ?
C3 C3A 1.5235(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.5008(15) . ?
C3A C10A 1.5310(14) . ?
C3A H3AA 1.0000 . ?
C4 C4A 1.3301(16) . ?
C4 H4A 0.9500 . ?
C4A C9B 1.5178(15) . ?
C5A C6 1.3787(15) . ?
C5A C9A 1.3929(15) . ?
C6 C7 1.3952(16) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3926(16) . ?
C7 H7A 0.9500 . ?
C8 C9 1.4022(15) . ?
C8 H8A 0.9500 . ?
C9 C9A 1.3828(15) . ?
C9 H9A 0.9500 . ?
C9A C9B 1.5090(15) . ?
C9B C10 1.5748(14) . ?
C9B H9BA 1.0000 . ?
C10 C11 1.5203(15) . ?
C10 C10A 1.5238(15) . ?
C10 H10A 1.0000 . ?
C10A H10B 1.0000 . ?
C12 C17 1.3933(15) . ?
C12 C13 1.4046(15) . ?
C13 C14 1.3845(16) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3964(16) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3868(16) . ?
C16 C17 1.3956(15) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 D19A 0.9800 . ?
C19 D19B 0.9800 . ?
C19 D19C 0.9800 . ?
C20 D20A 0.9800 . ?
C20 D20B 0.9800 . ?
C20 D20C 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
O6 S1 C19 106.39(6) . . ?
O6 S1 C20 105.08(6) . . ?
C19 S1 C20 98.44(7) . . ?
C11 O3 H3 108.7(13) . . ?
C15 O4 C18 116.89(9) . . ?
C5A O5 C4A 106.64(8) . . ?
C1 N2 C12 126.89(9) . . ?
C1 N2 C3 111.54(9) . . ?
C12 N2 C3 121.20(9) . . ?
O1 C1 N2 126.90(10) . . ?
O1 C1 C10A 126.17(10) . . ?
N2 C1 C10A 106.84(9) . . ?
N2 C3 C3A 102.43(8) . . ?
N2 C3 H3A 111.3 . . ?
C3A C3 H3A 111.3 . . ?
N2 C3 H3B 111.3 . . ?
C3A C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C4 C3A C3 119.03(9) . . ?
C4 C3A C10A 108.36(9) . . ?
C3 C3A C10A 101.35(8) . . ?
C4 C3A H3AA 109.2 . . ?
C3 C3A H3AA 109.2 . . ?
C10A C3A H3AA 109.2 . . ?
C4A C4 C3A 113.34(10) . . ?
C4A C4 H4A 123.3 . . ?
C3A C4 H4A 123.3 . . ?
C4 C4A O5 124.43(10) . . ?
C4 C4A C9B 125.07(10) . . ?
O5 C4A C9B 110.50(9) . . ?
C6 C5A O5 123.84(10) . . ?
C6 C5A C9A 123.47(10) . . ?
O5 C5A C9A 112.69(9) . . ?
C5A C6 C7 116.49(10) . . ?
C5A C6 H6A 121.8 . . ?
C7 C6 H6A 121.8 . . ?
C8 C7 C6 121.36(10) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C9 120.78(11) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C9A C9 C8 118.30(10) . . ?
C9A C9 H9A 120.8 . . ?
C8 C9 H9A 120.8 . . ?
C9 C9A C5A 119.58(10) . . ?
C9 C9A C9B 132.83(10) . . ?
C5A C9A C9B 107.47(9) . . ?
C9A C9B C4A 100.44(8) . . ?
C9A C9B C10 119.55(9) . . ?
C4A C9B C10 114.54(9) . . ?
C9A C9B H9BA 107.2 . . ?
C4A C9B H9BA 107.2 . . ?
C10 C9B H9BA 107.2 . . ?
C11 C10 C10A 112.17(9) . . ?
C11 C10 C9B 107.97(8) . . ?
C10A C10 C9B 108.75(8) . . ?
C11 C10 H10A 109.3 . . ?
C10A C10 H10A 109.3 . . ?
C9B C10 H10A 109.3 . . ?
C1 C10A C10 119.14(9) . . ?
C1 C10A C3A 103.50(8) . . ?
C10 C10A C3A 113.97(9) . . ?
C1 C10A H10B 106.5 . . ?
C10 C10A H10B 106.5 . . ?
C3A C10A H10B 106.5 . . ?
O2 C11 O3 123.84(10) . . ?
O2 C11 C10 124.00(10) . . ?
O3 C11 C10 112.13(9) . . ?
C17 C12 C13 118.51(10) . . ?
C17 C12 N2 119.12(10) . . ?
C13 C12 N2 122.34(10) . . ?
C14 C13 C12 119.93(11) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 121.24(11) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
O4 C15 C16 124.72(10) . . ?
O4 C15 C14 116.14(10) . . ?
C16 C15 C14 119.12(10) . . ?
C15 C16 C17 119.83(11) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C12 C17 C16 121.32(10) . . ?
C12 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S1 C19 D19A 109.5 . . ?
S1 C19 D19B 109.5 . . ?
D19A C19 D19B 109.5 . . ?
S1 C19 D19C 109.5 . . ?
D19A C19 D19C 109.5 . . ?
D19B C19 D19C 109.5 . . ?
S1 C20 D20A 109.5 . . ?
S1 C20 D20B 109.5 . . ?
D20A C20 D20B 109.5 . . ?
S1 C20 D20C 109.5 . . ?
D20A C20 D20C 109.5 . . ?
D20B C20 D20C 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
C12 N2 C1 O1 3.51(19) . . . . ?
C3 N2 C1 O1 176.57(11) . . . . ?
C12 N2 C1 C10A -173.10(10) . . . . ?
C3 N2 C1 C10A -0.05(12) . . . . ?
C1 N2 C3 C3A 23.03(11) . . . . ?
C12 N2 C3 C3A -163.47(9) . . . . ?
N2 C3 C3A C4 -153.95(9) . . . . ?
N2 C3 C3A C10A -35.33(10) . . . . ?
C3 C3A C4 C4A 158.64(10) . . . . ?
C10A C3A C4 C4A 43.72(13) . . . . ?
C3A C4 C4A O5 -174.71(10) . . . . ?
C3A C4 C4A C9B 5.27(16) . . . . ?
C5A O5 C4A C4 166.87(11) . . . . ?
C5A O5 C4A C9B -13.11(12) . . . . ?
C4A O5 C5A C6 -175.09(11) . . . . ?
C4A O5 C5A C9A 5.13(12) . . . . ?
O5 C5A C6 C7 178.98(10) . . . . ?
C9A C5A C6 C7 -1.25(17) . . . . ?
C5A C6 C7 C8 -0.18(17) . . . . ?
C6 C7 C8 C9 1.27(18) . . . . ?
C7 C8 C9 C9A -0.92(17) . . . . ?
C8 C9 C9A C5A -0.45(16) . . . . ?
C8 C9 C9A C9B 175.06(11) . . . . ?
C6 C5A C9A C9 1.60(17) . . . . ?
O5 C5A C9A C9 -178.61(10) . . . . ?
C6 C5A C9A C9B -174.95(10) . . . . ?
O5 C5A C9A C9B 4.84(13) . . . . ?
C9 C9A C9B C4A 172.48(12) . . . . ?
C5A C9A C9B C4A -11.61(11) . . . . ?
C9 C9A C9B C10 46.32(17) . . . . ?
C5A C9A C9B C10 -137.77(10) . . . . ?
C4 C4A C9B C9A -164.76(11) . . . . ?
O5 C4A C9B C9A 15.22(11) . . . . ?
C4 C4A C9B C10 -35.30(16) . . . . ?
O5 C4A C9B C10 144.68(9) . . . . ?
C9A C9B C10 C11 -108.07(11) . . . . ?
C4A C9B C10 C11 132.72(10) . . . . ?
C9A C9B C10 C10A 129.98(10) . . . . ?
C4A C9B C10 C10A 10.77(12) . . . . ?
O1 C1 C10A C10 32.67(16) . . . . ?
N2 C1 C10A C10 -150.68(9) . . . . ?
O1 C1 C10A C3A 160.42(11) . . . . ?
N2 C1 C10A C3A -22.93(11) . . . . ?
C11 C10 C10A C1 39.73(13) . . . . ?
C9B C10 C10A C1 159.08(9) . . . . ?
C11 C10 C10A C3A -82.98(11) . . . . ?
C9B C10 C10A C3A 36.37(12) . . . . ?
C4 C3A C10A C1 161.84(9) . . . . ?
C3 C3A C10A C1 35.82(10) . . . . ?
C4 C3A C10A C10 -67.25(11) . . . . ?
C3 C3A C10A C10 166.72(9) . . . . ?
C10A C10 C11 O2 26.51(15) . . . . ?
C9B C10 C11 O2 -93.30(12) . . . . ?
C10A C10 C11 O3 -155.77(9) . . . . ?
C9B C10 C11 O3 84.42(11) . . . . ?
C1 N2 C12 C17 172.05(10) . . . . ?
C3 N2 C12 C17 -0.40(15) . . . . ?
C1 N2 C12 C13 -10.08(17) . . . . ?
C3 N2 C12 C13 177.47(10) . . . . ?
C17 C12 C13 C14 1.48(17) . . . . ?
N2 C12 C13 C14 -176.40(11) . . . . ?
C12 C13 C14 C15 0.17(19) . . . . ?
C18 O4 C15 C16 -1.50(17) . . . . ?
C18 O4 C15 C14 179.65(11) . . . . ?
C13 C14 C15 O4 177.27(11) . . . . ?
C13 C14 C15 C16 -1.65(18) . . . . ?
O4 C15 C16 C17 -177.39(11) . . . . ?
C14 C15 C16 C17 1.43(17) . . . . ?
C13 C12 C17 C16 -1.70(17) . . . . ?
N2 C12 C17 C16 176.26(10) . . . . ?
C15 C16 C17 C12 0.24(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 S1 0.91(2) 2.74(2) 3.5854(9) 153.7(17) . yes
O3 H3 O6 0.91(2) 1.70(2) 2.6063(12) 176(2) . yes
C3 H3B O1 0.99 2.50 3.4384(14) 157.1 1_455 yes
C13 H13A O1 0.95 2.25 2.8868(14) 123.5 . yes
C17 H17A O1 0.95 2.54 3.3221(14) 139.5 1_455 yes
C19 D19A O2 0.98 2.39 3.3349(16) 162.7 2_675 yes

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.056


# start Validation Reply Form
_vrf_PLAT910_ZV2050              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 16 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_12c
_database_code_depnum_ccdc_archive 'CCDC 2513917'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-12-07 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O5, C2 H6 O S'
_chemical_formula_sum            'C23 H29 N O6 S'
_chemical_formula_weight         447.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.14531(17)
_cell_length_b                   11.43369(19)
_cell_length_c                   21.5910(4)
_cell_angle_alpha                100.0863(15)
_cell_angle_beta                 90.7070(14)
_cell_angle_gamma                90.2151(13)
_cell_volume                     2222.55(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19873
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      79.56

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.629
_shelx_estimated_absorpt_T_min   0.615
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30564
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.927
_diffrn_reflns_theta_max         83.712
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             11897
_reflns_number_gt                11411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    0.966

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+9.6P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11897
_refine_ls_number_parameters     1108
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0914
_refine_ls_wR_factor_ref         0.2067
_refine_ls_wR_factor_gt          0.2050
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C -0.2046(10) 0.1764(9) 0.2093(4) 0.0382(19) Uani 1 1 d . . . . .
H1A H -0.2228 0.0929 0.1890 0.046 Uiso 1 1 calc R U . . .
H1B H -0.2989 0.2191 0.2132 0.046 Uiso 1 1 calc R U . . .
C2 C -0.1303(11) 0.1819(8) 0.2754(4) 0.0400(19) Uani 1 1 d . . . . .
H2A H -0.1801 0.2401 0.3075 0.048 Uiso 1 1 calc R U . . .
H2B H -0.1333 0.1031 0.2884 0.048 Uiso 1 1 calc R U . . .
C3 C 0.0278(10) 0.2204(8) 0.2672(4) 0.0378(19) Uani 1 1 d . . . . .
H3A H 0.0704 0.2612 0.3076 0.045 Uiso 1 1 calc R U . . .
H3B H 0.0893 0.1513 0.2504 0.045 Uiso 1 1 calc R U . . .
C3A C 0.0148(10) 0.3047(7) 0.2204(4) 0.0331(17) Uani 1 1 d . . . . .
C4 C -0.0511(12) 0.4247(8) 0.2489(4) 0.042(2) Uani 1 1 d . . . . .
H4A H -0.1591 0.4197 0.2495 0.051 Uiso 1 1 calc R U . . .
H4B H -0.0143 0.4515 0.2924 0.051 Uiso 1 1 calc R U . . .
N5 N -0.0023(9) 0.5069(6) 0.2068(4) 0.0403(17) Uani 1 1 d . . . . .
C6 C 0.1172(10) 0.4617(8) 0.1740(4) 0.0394(19) Uani 1 1 d . . . . .
O6 O 0.1883(8) 0.5143(6) 0.1386(3) 0.0488(16) Uani 1 1 d . . . . .
C6A C 0.1557(10) 0.3419(8) 0.1914(4) 0.0357(18) Uani 1 1 d . . . . .
H6A H 0.2311 0.3570 0.2258 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2219(10) 0.2527(8) 0.1371(4) 0.0342(17) Uani 1 1 d . . . . .
H7 H 0.2614 0.1854 0.1561 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1058(9) 0.1996(8) 0.0881(4) 0.0344(17) Uani 1 1 d . . . . .
H8 H 0.0642 0.2652 0.0684 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0178(10) 0.1469(8) 0.1227(4) 0.0355(18) Uani 1 1 d . . . . .
O9 O -0.0447(8) 0.0440(6) 0.1114(3) 0.0465(15) Uani 1 1 d . . . . .
C9A C -0.0959(10) 0.2368(7) 0.1706(4) 0.0314(16) Uani 1 1 d . . . . .
H9A H -0.1488 0.2947 0.1488 0.038 Uiso 1 1 calc R U . . .
C10 C -0.0654(12) 0.6212(9) 0.2113(5) 0.050(2) Uani 1 1 d . . . . .
C11 C -0.0669(13) 0.6796(10) 0.1588(6) 0.057(3) Uani 1 1 d . . . . .
H11 H -0.0246 0.6430 0.1203 0.068 Uiso 1 1 calc R U . . .
C12 C -0.1310(16) 0.7917(12) 0.1638(7) 0.073(4) Uani 1 1 d . . . . .
H12 H -0.1285 0.8327 0.1291 0.088 Uiso 1 1 calc R U . . .
C13 C -0.1993(19) 0.8441(12) 0.2198(10) 0.097(6) Uani 1 1 d . . . . .
H13 H -0.2503 0.9169 0.2220 0.116 Uiso 1 1 calc R U . . .
C14 C -0.191(2) 0.7885(11) 0.2716(7) 0.088(5) Uani 1 1 d . . . . .
H14 H -0.2286 0.8269 0.3108 0.105 Uiso 1 1 calc R U . . .
C15 C -0.1286(16) 0.6760(10) 0.2667(7) 0.069(3) Uani 1 1 d . . . . .
H15 H -0.1293 0.6365 0.3019 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3516(10) 0.3083(8) 0.1091(4) 0.0355(18) Uani 1 1 d . . . . .
O16 O 0.4555(7) 0.3405(6) 0.1533(3) 0.0395(14) Uani 1 1 d . . . . .
H16 H 0.5315 0.3731 0.1362 0.059 Uiso 1 1 d R U . . .
O17 O 0.3618(8) 0.3217(7) 0.0553(3) 0.0477(16) Uani 1 1 d . . . . .
C17 C 0.1637(10) 0.1044(9) 0.0360(4) 0.0399(19) Uani 1 1 d . . . . .
H17A H 0.2501 0.1360 0.0170 0.048 Uiso 1 1 calc R U . . .
H17B H 0.1956 0.0351 0.0544 0.048 Uiso 1 1 calc R U . . .
C18 C 0.0491(10) 0.0642(9) -0.0151(4) 0.0395(19) Uani 1 1 d . . . . .
O18 O -0.0563(8) 0.1199(8) -0.0210(3) 0.0550(18) Uani 1 1 d . . . . .
C19 C 0.0830(12) -0.0504(10) -0.0577(5) 0.052(2) Uani 1 1 d . . . . .
H19A H 0.1892 -0.0605 -0.0604 0.078 Uiso 1 1 calc R U . . .
H19B H 0.0420 -0.0490 -0.0997 0.078 Uiso 1 1 calc R U . . .
H19C H 0.0398 -0.1166 -0.0408 0.078 Uiso 1 1 calc R U . . .
S1 S 0.7406(3) 0.4750(3) 0.06190(14) 0.0422(5) Uani 1 1 d . . . . .
O1 O 0.6925(7) 0.4331(7) 0.1217(3) 0.0444(15) Uani 1 1 d . . . . .
C20 C 0.6051(15) 0.5729(11) 0.0437(6) 0.065(3) Uani 1 1 d . . . . .
H20A H 0.5124 0.5298 0.0346 0.097 Uiso 1 1 calc R U . . .
H20B H 0.6346 0.6060 0.0068 0.097 Uiso 1 1 calc R U . . .
H20C H 0.5929 0.6375 0.0796 0.097 Uiso 1 1 calc R U . . .
C21 C 0.6993(14) 0.3558(12) -0.0004(5) 0.063(3) Uani 1 1 d . . . . .
H21A H 0.7755 0.2952 -0.0024 0.095 Uiso 1 1 calc R U . . .
H21B H 0.6950 0.3855 -0.0403 0.095 Uiso 1 1 calc R U . . .
H21C H 0.6046 0.3208 0.0071 0.095 Uiso 1 1 calc R U . . .
C22 C 0.2896(10) 0.8073(8) 0.7883(4) 0.0369(18) Uani 1 1 d . . . . .
H22A H 0.2681 0.8906 0.8072 0.044 Uiso 1 1 calc R U . . .
H22B H 0.1967 0.7617 0.7827 0.044 Uiso 1 1 calc R U . . .
C23 C 0.3671(11) 0.8015(9) 0.7245(4) 0.042(2) Uani 1 1 d . . . . .
H23A H 0.3152 0.7458 0.6911 0.051 Uiso 1 1 calc R U . . .
H23B H 0.3696 0.8810 0.7123 0.051 Uiso 1 1 calc R U . . .
C24 C 0.5214(10) 0.7583(8) 0.7341(4) 0.0359(18) Uani 1 1 d . . . . .
H24A H 0.5880 0.8258 0.7494 0.043 Uiso 1 1 calc R U . . .
H24B H 0.5599 0.7129 0.6944 0.043 Uiso 1 1 calc R U . . .
C24A C 0.5048(9) 0.6774(7) 0.7842(3) 0.0283(15) Uani 1 1 d . . . . .
C25 C 0.4345(11) 0.5606(8) 0.7567(4) 0.0395(19) Uani 1 1 d . . . . .
H25A H 0.3266 0.5669 0.7559 0.047 Uiso 1 1 calc R U . . .
H25B H 0.4691 0.5315 0.7135 0.047 Uiso 1 1 calc R U . . .
N26 N 0.4832(9) 0.4823(7) 0.8002(4) 0.0428(17) Uani 1 1 d . . . . .
C27 C 0.6045(10) 0.5257(8) 0.8339(4) 0.0390(19) Uani 1 1 d . . . . .
O27 O 0.6712(8) 0.4763(6) 0.8706(3) 0.0474(16) Uani 1 1 d . . . . .
C27A C 0.6463(9) 0.6425(7) 0.8139(4) 0.0321(17) Uani 1 1 d . . . . .
H27A H 0.7196 0.6242 0.7796 0.039 Uiso 1 1 calc R U . . .
C28 C 0.7156(9) 0.7346(8) 0.8664(3) 0.0309(16) Uani 1 1 d . . . . .
H28 H 0.7547 0.7999 0.8458 0.037 Uiso 1 1 calc R U . . .
C29 C 0.6023(9) 0.7921(8) 0.9154(4) 0.0352(18) Uani 1 1 d . . . . .
H29 H 0.5586 0.7280 0.9355 0.042 Uiso 1 1 calc R U . . .
C30 C 0.4808(9) 0.8440(8) 0.8789(4) 0.0312(16) Uani 1 1 d . . . . .
O30 O 0.4552(8) 0.9472(6) 0.8873(3) 0.0445(15) Uani 1 1 d . . . . .
C30A C 0.3972(9) 0.7520(8) 0.8305(4) 0.0328(17) Uani 1 1 d . . . . .
H30A H 0.3419 0.6974 0.8533 0.039 Uiso 1 1 calc R U . . .
C31 C 0.4176(14) 0.3704(11) 0.7992(8) 0.0748(16) Uani 1 1 d . . . . .
C32 C 0.4178(14) 0.3157(11) 0.8524(8) 0.0748(16) Uani 1 1 d . . . . .
H32 H 0.4670 0.3520 0.8899 0.090 Uiso 1 1 calc R U . . .
C33 C 0.3444(14) 0.2065(11) 0.8498(8) 0.0748(16) Uani 1 1 d . . . . .
H33 H 0.3453 0.1688 0.8857 0.090 Uiso 1 1 calc R U . . .
C34 C 0.2694(14) 0.1522(11) 0.7944(8) 0.0748(16) Uani 1 1 d . . . . .
H34 H 0.2191 0.0790 0.7934 0.090 Uiso 1 1 calc R U . . .
C35 C 0.2694(14) 0.2055(11) 0.7423(8) 0.0748(16) Uani 1 1 d . . . . .
H35 H 0.2203 0.1683 0.7049 0.090 Uiso 1 1 calc R U . . .
C36 C 0.3415(14) 0.3146(11) 0.7436(8) 0.0748(16) Uani 1 1 d . . . . .
H36 H 0.3396 0.3514 0.7075 0.090 Uiso 1 1 calc R U . . .
C37 C 0.8462(10) 0.6823(8) 0.8963(4) 0.0365(18) Uani 1 1 d . . . . .
O37 O 0.9497(7) 0.6507(6) 0.8545(3) 0.0397(14) Uani 1 1 d . . . . .
H37 H 1.0260 0.6195 0.8726 0.060 Uiso 1 1 d R U . . .
O38 O 0.8563(7) 0.6721(6) 0.9509(3) 0.0419(15) Uani 1 1 d . . . . .
C38 C 0.6607(10) 0.8873(8) 0.9665(4) 0.0372(18) Uani 1 1 d . . . . .
H38A H 0.7477 0.8568 0.9861 0.045 Uiso 1 1 calc R U . . .
H38B H 0.6922 0.9561 0.9477 0.045 Uiso 1 1 calc R U . . .
C39 C 0.5513(10) 0.9278(10) 1.0162(4) 0.041(2) Uani 1 1 d . . . . .
O39 O 0.4436(8) 0.8753(7) 1.0234(3) 0.0469(16) Uani 1 1 d . . . . .
C40 C 0.5817(13) 1.0494(12) 1.0576(5) 0.059(3) Uani 1 1 d . . . . .
H40A H 0.6875 1.0611 1.0635 0.088 Uiso 1 1 calc R U . . .
H40B H 0.5356 1.0523 1.0985 0.088 Uiso 1 1 calc R U . . .
H40C H 0.5414 1.1123 1.0370 0.088 Uiso 1 1 calc R U . . .
S2 S 0.2353(3) 0.5262(3) 0.94989(16) 0.0547(7) Uani 1 1 d . . . . .
O2 O 0.1926(7) 0.5676(7) 0.8894(3) 0.0496(17) Uani 1 1 d . . . . .
C41 C 0.0949(14) 0.4266(14) 0.9636(7) 0.075(4) Uani 1 1 d . . . . .
H41A H 0.0011 0.4682 0.9676 0.113 Uiso 1 1 calc R U . . .
H41B H 0.1167 0.3967 1.0026 0.113 Uiso 1 1 calc R U . . .
H41C H 0.0894 0.3598 0.9284 0.113 Uiso 1 1 calc R U . . .
C42 C 0.1943(12) 0.6457(12) 1.0124(5) 0.057(3) Uani 1 1 d . . . . .
H42A H 0.2685 0.7084 1.0142 0.086 Uiso 1 1 calc R U . . .
H42B H 0.1943 0.6164 1.0524 0.086 Uiso 1 1 calc R U . . .
H42C H 0.0978 0.6779 1.0049 0.086 Uiso 1 1 calc R U . . .
C43 C 0.8909(12) 0.4356(9) 0.4590(5) 0.049(2) Uani 1 1 d . . . . .
H43A H 0.9341 0.3614 0.4685 0.058 Uiso 1 1 calc R U . . .
H43B H 0.8004 0.4154 0.4337 0.058 Uiso 1 1 calc R U . . .
C44 C 1.0003(11) 0.5010(10) 0.4232(4) 0.049(2) Uani 1 1 d . . . . .
H44A H 0.9538 0.5211 0.3848 0.059 Uiso 1 1 calc R U . . .
H44B H 1.0866 0.4507 0.4109 0.059 Uiso 1 1 calc R U . . .
C45 C 1.0457(10) 0.6149(10) 0.4689(5) 0.046(2) Uani 1 1 d . . . . .
H45A H 1.1298 0.6003 0.4958 0.055 Uiso 1 1 calc R U . . .
H45B H 1.0710 0.6798 0.4460 0.055 Uiso 1 1 calc R U . . .
C45A C 0.9079(9) 0.6436(8) 0.5076(4) 0.0340(17) Uani 1 1 d . . . . .
C46 C 0.7887(9) 0.6978(9) 0.4695(4) 0.0386(19) Uani 1 1 d . . . . .
H46A H 0.8319 0.7555 0.4456 0.046 Uiso 1 1 calc R U . . .
H46B H 0.7362 0.6352 0.4400 0.046 Uiso 1 1 calc R U . . .
N47 N 0.6904(8) 0.7573(7) 0.5187(3) 0.0322(14) Uani 1 1 d . . . . .
C48 C 0.7641(9) 0.7879(7) 0.5759(4) 0.0307(16) Uani 1 1 d . . . . .
O48 O 0.7161(6) 0.8441(5) 0.6243(3) 0.0324(12) Uani 1 1 d . . . . .
C48A C 0.9193(9) 0.7427(8) 0.5666(4) 0.0337(17) Uani 1 1 d . . . . .
H48A H 0.9808 0.8084 0.5556 0.040 Uiso 1 1 calc R U . . .
C49 C 0.9875(9) 0.7041(7) 0.6249(4) 0.0316(16) Uani 1 1 d . . . . .
H49 H 1.0938 0.6901 0.6162 0.038 Uiso 1 1 calc R U . . .
C50 C 0.9220(9) 0.5858(8) 0.6377(4) 0.0353(17) Uani 1 1 d . . . . .
H50 H 0.8151 0.5967 0.6458 0.042 Uiso 1 1 calc R U . . .
C51 C 0.9418(9) 0.4951(8) 0.5770(4) 0.0360(18) Uani 1 1 d . . . . .
O51 O 1.0217(8) 0.4122(6) 0.5756(3) 0.0464(15) Uani 1 1 d . . . . .
C51A C 0.8573(9) 0.5232(7) 0.5208(4) 0.0345(17) Uani 1 1 d . . . . .
H51A H 0.7499 0.5243 0.5291 0.041 Uiso 1 1 calc R U . . .
C52 C 0.5489(9) 0.7963(7) 0.5059(4) 0.0335(17) Uani 1 1 d . . . . .
C53 C 0.4442(10) 0.8253(8) 0.5519(4) 0.0365(18) Uani 1 1 d . . . . .
H53 H 0.4668 0.8177 0.5941 0.044 Uiso 1 1 calc R U . . .
C54 C 0.3078(10) 0.8649(9) 0.5376(5) 0.042(2) Uani 1 1 d . . . . .
H54 H 0.2386 0.8864 0.5700 0.050 Uiso 1 1 calc R U . . .
C55 C 0.2717(10) 0.8735(8) 0.4765(5) 0.042(2) Uani 1 1 d . . . . .
H55 H 0.1770 0.8987 0.4662 0.051 Uiso 1 1 calc R U . . .
C56 C 0.3758(11) 0.8446(8) 0.4302(4) 0.043(2) Uani 1 1 d . . . . .
H56 H 0.3513 0.8521 0.3882 0.052 Uiso 1 1 calc R U . . .
C57 C 0.5107(10) 0.8063(9) 0.4428(4) 0.0399(19) Uani 1 1 d . . . . .
H57 H 0.5793 0.7863 0.4100 0.048 Uiso 1 1 calc R U . . .
C58 C 0.9775(10) 0.8068(8) 0.6799(4) 0.0383(19) Uani 1 1 d . . . . .
O58 O 1.0358(7) 0.9057(6) 0.6751(3) 0.0383(13) Uani 1 1 d . . . . .
H58 H 0.9955 0.9640 0.7030 0.057 Uiso 0.35 1 d R U P A 2
O59 O 0.9091(7) 0.7907(6) 0.7293(3) 0.0382(13) Uani 1 1 d . . . . .
H59 H 0.8894 0.8616 0.7530 0.057 Uiso 0.65 1 d R U P B 1
C59 C 0.9926(10) 0.5392(8) 0.6924(4) 0.0378(18) Uani 1 1 d . . . . .
H59A H 1.0081 0.6062 0.7277 0.045 Uiso 1 1 calc R U . . .
H59B H 1.0896 0.5061 0.6795 0.045 Uiso 1 1 calc R U . . .
C60 C 0.8999(11) 0.4425(9) 0.7153(5) 0.046(2) Uani 1 1 d . . . . .
O60 O 0.7798(8) 0.4161(7) 0.6925(4) 0.0566(18) Uani 1 1 d . . . . .
C61 C 0.9662(13) 0.3908(9) 0.7696(5) 0.054(3) Uani 1 1 d . . . . .
H61A H 1.0658 0.4217 0.7784 0.081 Uiso 1 1 calc R U . . .
H61B H 0.9689 0.3040 0.7583 0.081 Uiso 1 1 calc R U . . .
H61C H 0.9065 0.4134 0.8072 0.081 Uiso 1 1 calc R U . . .
S3 S 0.8260(5) 0.0907(4) 0.7891(2) 0.0485(8) Uani 0.65 1 d D . P C 1
O3 O 0.8388(11) -0.0310(5) 0.8059(4) 0.0485(8) Uani 0.65 1 d D . P C 1
C62 C 0.6670(10) 0.0889(10) 0.7413(5) 0.0485(8) Uani 0.65 1 d D . P C 1
H62A H 0.6844 0.0402 0.7001 0.073 Uiso 0.65 1 calc R U P C 1
H62B H 0.6436 0.1702 0.7361 0.073 Uiso 0.65 1 calc R U P C 1
H62C H 0.5851 0.0554 0.7614 0.073 Uiso 0.65 1 calc R U P C 1
C63 C 0.7543(15) 0.1839(8) 0.8558(4) 0.0485(8) Uani 0.65 1 d D . P C 1
H63A H 0.8282 0.1963 0.8896 0.073 Uiso 0.65 1 calc R U P C 1
H63B H 0.6673 0.1465 0.8701 0.073 Uiso 0.65 1 calc R U P C 1
H63C H 0.7277 0.2606 0.8447 0.073 Uiso 0.65 1 calc R U P C 1
S3' S 0.7735(9) 0.0456(7) 0.7861(4) 0.059(2) Uani 0.35 1 d D . P D 2
O3' O 0.9177(15) 0.0702(13) 0.7580(9) 0.059(2) Uani 0.35 1 d D . P D 2
C62' C 0.805(3) -0.0703(15) 0.8294(10) 0.059(2) Uani 0.35 1 d D . P D 2
H62D H 0.8224 -0.1446 0.8002 0.089 Uiso 0.35 1 calc R U P D 2
H62E H 0.7188 -0.0797 0.8548 0.089 Uiso 0.35 1 calc R U P D 2
H62F H 0.8903 -0.0506 0.8571 0.089 Uiso 0.35 1 calc R U P D 2
C63' C 0.750(3) 0.1587(14) 0.8525(9) 0.059(2) Uani 0.35 1 d D . P D 2
H63D H 0.7289 0.2340 0.8385 0.089 Uiso 0.35 1 calc R U P D 2
H63E H 0.8394 0.1670 0.8783 0.089 Uiso 0.35 1 calc R U P D 2
H63F H 0.6681 0.1376 0.8774 0.089 Uiso 0.35 1 calc R U P D 2
C64 C 0.3958(12) 0.4754(10) 0.5544(5) 0.051(2) Uani 1 1 d . . . . .
H64A H 0.3069 0.4910 0.5801 0.062 Uiso 1 1 calc R U . . .
H64B H 0.4382 0.5522 0.5480 0.062 Uiso 1 1 calc R U . . .
C65 C 0.5103(11) 0.4024(11) 0.5868(5) 0.052(3) Uani 1 1 d . . . . .
H65A H 0.5980 0.4517 0.6005 0.063 Uiso 1 1 calc R U . . .
H65B H 0.4671 0.3773 0.6243 0.063 Uiso 1 1 calc R U . . .
C66 C 0.5513(10) 0.2962(10) 0.5398(4) 0.042(2) Uani 1 1 d . . . . .
H66A H 0.5789 0.2292 0.5609 0.051 Uiso 1 1 calc R U . . .
H66B H 0.6340 0.3148 0.5139 0.051 Uiso 1 1 calc R U . . .
C66A C 0.4091(9) 0.2659(8) 0.4984(4) 0.0345(17) Uani 1 1 d . . . . .
C67 C 0.2888(10) 0.2091(8) 0.5321(4) 0.0377(18) Uani 1 1 d . . . . .
H67A H 0.3290 0.1471 0.5541 0.045 Uiso 1 1 calc R U . . .
H67B H 0.2381 0.2694 0.5628 0.045 Uiso 1 1 calc R U . . .
N68 N 0.1907(8) 0.1577(7) 0.4804(3) 0.0347(15) Uani 1 1 d . . . . .
C69 C 0.2612(9) 0.1398(8) 0.4251(4) 0.0336(17) Uani 1 1 d . . . . .
O69 O 0.2108(7) 0.0925(6) 0.3734(3) 0.0361(13) Uani 1 1 d . . . . .
C69A C 0.4189(10) 0.1801(8) 0.4371(4) 0.0346(17) Uani 1 1 d . . . . .
H69A H 0.4770 0.1102 0.4450 0.042 Uiso 1 1 calc R U . . .
C70 C 0.4888(9) 0.2269(8) 0.3810(4) 0.0357(18) Uani 1 1 d . . . . .
H70 H 0.5951 0.2401 0.3915 0.043 Uiso 1 1 calc R U . . .
C71 C 0.4251(9) 0.3494(8) 0.3730(4) 0.0342(17) Uani 1 1 d . . . . .
H71 H 0.3184 0.3383 0.3629 0.041 Uiso 1 1 calc R U . . .
C72 C 0.4404(9) 0.4314(8) 0.4367(4) 0.0376(18) Uani 1 1 d . . . . .
O72 O 0.5195(8) 0.5160(7) 0.4423(3) 0.0503(16) Uani 1 1 d . . . . .
C72A C 0.3600(9) 0.3945(8) 0.4902(4) 0.0347(17) Uani 1 1 d . . . . .
H72A H 0.2523 0.3949 0.4817 0.042 Uiso 1 1 calc R U . . .
C73 C 0.0485(10) 0.1200(8) 0.4928(4) 0.0377(18) Uani 1 1 d . . . . .
C74 C -0.0565(10) 0.0912(8) 0.4426(4) 0.0379(18) Uani 1 1 d . . . . .
H74 H -0.0321 0.0989 0.4008 0.046 Uiso 1 1 calc R U . . .
C75 C -0.1947(10) 0.0519(9) 0.4560(5) 0.045(2) Uani 1 1 d . . . . .
H75 H -0.2655 0.0336 0.4231 0.054 Uiso 1 1 calc R U . . .
C76 C -0.2305(10) 0.0389(8) 0.5163(5) 0.041(2) Uani 1 1 d . . . . .
H76 H -0.3245 0.0102 0.5248 0.050 Uiso 1 1 calc R U . . .
C77 C -0.1278(10) 0.0682(9) 0.5644(4) 0.042(2) Uani 1 1 d . . . . .
H77 H -0.1530 0.0624 0.6063 0.050 Uiso 1 1 calc R U . . .
C78 C 0.0097(10) 0.1054(9) 0.5520(4) 0.0407(19) Uani 1 1 d . . . . .
H78 H 0.0797 0.1214 0.5853 0.049 Uiso 1 1 calc R U . . .
C79 C 0.4794(10) 0.1303(9) 0.3236(4) 0.039(2) Uani 1 1 d . . . . .
O79 O 0.5357(7) 0.0333(6) 0.3244(3) 0.0424(14) Uani 1 1 d . . . . .
H79 H 0.5019 -0.0197 0.2915 0.064 Uiso 0.35 1 d R U P E 2
O80 O 0.4102(8) 0.1588(6) 0.2745(3) 0.0431(14) Uani 1 1 d . . . . .
H80 H 0.3943 0.0926 0.2459 0.065 Uiso 0.65 1 d R U P F 1
C80 C 0.4940(11) 0.4043(9) 0.3222(4) 0.042(2) Uani 1 1 d . . . . .
H80A H 0.4952 0.3451 0.2828 0.050 Uiso 1 1 calc R U . . .
H80B H 0.5966 0.4262 0.3343 0.050 Uiso 1 1 calc R U . . .
C81 C 0.4128(12) 0.5137(9) 0.3105(5) 0.048(2) Uani 1 1 d . . . . .
O81 O 0.2866(9) 0.5313(7) 0.3259(4) 0.0593(19) Uani 1 1 d . . . . .
C82 C 0.4879(19) 0.5919(13) 0.2719(8) 0.090(5) Uani 1 1 d . . . . .
H82A H 0.5893 0.5660 0.2648 0.135 Uiso 1 1 calc R U . . .
H82B H 0.4868 0.6743 0.2942 0.135 Uiso 1 1 calc R U . . .
H82C H 0.4367 0.5866 0.2313 0.135 Uiso 1 1 calc R U . . .
S4 S 0.2645(5) 0.8889(4) 0.17286(19) 0.0517(8) Uani 0.65 1 d D . P G 1
O4 O 0.3389(11) 1.0079(5) 0.1806(4) 0.0517(8) Uani 0.65 1 d D . P G 1
C83 C 0.2149(14) 0.8678(10) 0.2492(4) 0.0517(8) Uani 0.65 1 d D . P G 1
H83A H 0.1353 0.9220 0.2645 0.078 Uiso 0.65 1 calc R U P G 1
H83B H 0.2996 0.8842 0.2777 0.078 Uiso 0.65 1 calc R U P G 1
H83C H 0.1823 0.7855 0.2476 0.078 Uiso 0.65 1 calc R U P G 1
C84 C 0.4029(11) 0.7804(8) 0.1620(6) 0.0517(8) Uani 0.65 1 d D . P G 1
H84A H 0.4464 0.7775 0.1205 0.078 Uiso 0.65 1 calc R U P G 1
H84B H 0.3606 0.7026 0.1647 0.078 Uiso 0.65 1 calc R U P G 1
H84C H 0.4785 0.8007 0.1946 0.078 Uiso 0.65 1 calc R U P G 1
S4' S 0.3085(16) 0.9127(13) 0.2112(6) 0.0456(19) Uani 0.15 1 d D . P H 2
O4' O 0.439(3) 0.874(3) 0.2450(13) 0.0456(19) Uani 0.15 1 d D . P H 2
C83' C 0.270(5) 0.797(2) 0.1471(13) 0.0456(19) Uani 0.15 1 d D . P H 2
H83D H 0.2277 0.7288 0.1629 0.068 Uiso 0.15 1 calc R U P H 2
H83E H 0.3601 0.7727 0.1247 0.068 Uiso 0.15 1 calc R U P H 2
H83F H 0.1995 0.8249 0.1184 0.068 Uiso 0.15 1 calc R U P H 2
C84' C 0.372(5) 1.015(3) 0.1650(15) 0.0456(19) Uani 0.15 1 d D . P H 2
H84D H 0.4045 1.0886 0.1926 0.068 Uiso 0.15 1 calc R U P H 2
H84E H 0.2934 1.0337 0.1372 0.068 Uiso 0.15 1 calc R U P H 2
H84F H 0.4548 0.9809 0.1396 0.068 Uiso 0.15 1 calc R U P H 2
S4" S 0.3283(13) 0.8179(10) 0.2014(4) 0.0456(19) Uani 0.2 1 d D . P I 3
O4" O 0.4726(16) 0.870(3) 0.2262(10) 0.0456(19) Uani 0.2 1 d D . P I 3
C83" C 0.203(2) 0.850(3) 0.2637(9) 0.0456(19) Uani 0.2 1 d D . P I 3
H83G H 0.2255 0.8017 0.2958 0.068 Uiso 0.2 1 calc R U P I 3
H83H H 0.1031 0.8317 0.2475 0.068 Uiso 0.2 1 calc R U P I 3
H83I H 0.2097 0.9344 0.2824 0.068 Uiso 0.2 1 calc R U P I 3
C84" C 0.252(3) 0.917(3) 0.1553(14) 0.0456(19) Uani 0.2 1 d D . P I 3
H84G H 0.3087 0.9135 0.1168 0.068 Uiso 0.2 1 calc R U P I 3
H84H H 0.2544 0.9976 0.1794 0.068 Uiso 0.2 1 calc R U P I 3
H84I H 0.1504 0.8933 0.1441 0.068 Uiso 0.2 1 calc R U P I 3


_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
C1 C9A 1.543(11) . ?
C1 C2 1.564(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.531(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C3A 1.516(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.531(12) . ?
C3A C6A 1.531(12) . ?
C3A C9A 1.568(11) . ?
C4 N5 1.488(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N5 C6 1.363(12) . ?
N5 C10 1.419(12) . ?
C6 O6 1.241(11) . ?
C6 C6A 1.523(12) . ?
C6A C7 1.544(11) . ?
C6A H6A 1.0000 . ?
C7 C16 1.524(11) . ?
C7 C8 1.536(12) . ?
C7 H7 1.0000 . ?
C8 C17 1.522(12) . ?
C8 C9 1.541(11) . ?
C8 H8 1.0000 . ?
C9 O9 1.182(10) . ?
C9 C9A 1.512(12) . ?
C9A H9A 1.0000 . ?
C10 C15 1.383(16) . ?
C10 C11 1.413(14) . ?
C11 C12 1.399(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.41(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.38(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O17 1.202(10) . ?
C16 O16 1.343(10) . ?
O16 H16 0.8998 . ?
C17 C18 1.523(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O18 1.176(12) . ?
C18 C19 1.499(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
S1 O1 1.522(6) . ?
S1 C20 1.759(11) . ?
S1 C21 1.775(13) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C30A 1.543(11) . ?
C22 C23 1.548(12) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.521(13) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24A 1.549(11) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24A C25 1.503(12) . ?
C24A C27A 1.522(11) . ?
C24A C30A 1.557(11) . ?
C25 N26 1.473(12) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N26 C27 1.361(12) . ?
N26 C31 1.408(14) . ?
C27 O27 1.212(11) . ?
C27 C27A 1.523(11) . ?
C27A C28 1.534(12) . ?
C27A H27A 1.0000 . ?
C28 C37 1.524(11) . ?
C28 C29 1.554(11) . ?
C28 H28 1.0000 . ?
C29 C38 1.498(13) . ?
C29 C30 1.534(11) . ?
C29 H29 1.0000 . ?
C30 O30 1.187(10) . ?
C30 C30A 1.541(12) . ?
C30A H30A 1.0000 . ?
C31 C32 1.40(2) . ?
C31 C36 1.43(2) . ?
C32 C33 1.407(16) . ?
C32 H32 0.9500 . ?
C33 C34 1.42(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.37(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.405(16) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 O38 1.207(10) . ?
C37 O37 1.324(10) . ?
O37 H37 0.9000 . ?
C38 C39 1.491(12) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 O39 1.177(12) . ?
C39 C40 1.538(15) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
S2 O2 1.512(6) . ?
S2 C41 1.775(12) . ?
S2 C42 1.789(13) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.540(15) . ?
C43 C51A 1.556(12) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.543(14) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C45A 1.525(12) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C45A C51A 1.525(12) . ?
C45A C48A 1.552(11) . ?
C45A C46 1.553(12) . ?
C46 N47 1.474(11) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
N47 C48 1.388(10) . ?
N47 C52 1.410(11) . ?
C48 O48 1.216(10) . ?
C48 C48A 1.515(12) . ?
C48A C49 1.532(11) . ?
C48A H48A 1.0000 . ?
C49 C58 1.521(11) . ?
C49 C50 1.547(11) . ?
C49 H49 1.0000 . ?
C50 C59 1.516(12) . ?
C50 C51 1.535(12) . ?
C50 H50 1.0000 . ?
C51 O51 1.196(11) . ?
C51 C51A 1.513(12) . ?
C51A H51A 1.0000 . ?
C52 C53 1.387(12) . ?
C52 C57 1.426(11) . ?
C53 C54 1.378(13) . ?
C53 H53 0.9500 . ?
C54 C55 1.375(14) . ?
C54 H54 0.9500 . ?
C55 C56 1.387(14) . ?
C55 H55 0.9500 . ?
C56 C57 1.351(13) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C58 O58 1.269(11) . ?
C58 O59 1.283(11) . ?
O58 H58 0.9000 . ?
O59 H59 0.9001 . ?
C59 C60 1.543(12) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 O60 1.213(13) . ?
C60 C61 1.525(14) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
S3 O3 1.503(3) . ?
S3 C63 1.769(3) . ?
S3 C62 1.770(4) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
S3' O3' 1.504(4) . ?
S3' C63' 1.771(4) . ?
S3' C62' 1.771(4) . ?
C62' H62D 0.9800 . ?
C62' H62E 0.9800 . ?
C62' H62F 0.9800 . ?
C63' H63D 0.9800 . ?
C63' H63E 0.9800 . ?
C63' H63F 0.9800 . ?
C64 C72A 1.556(12) . ?
C64 C65 1.574(16) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 C66 1.491(14) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 C66A 1.572(12) . ?
C66 H66A 0.9900 . ?
C66 H66B 0.9900 . ?
C66A C69A 1.506(12) . ?
C66A C67 1.530(11) . ?
C66A C72A 1.578(12) . ?
C67 N68 1.462(11) . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
N68 C69 1.349(10) . ?
N68 C73 1.412(11) . ?
C69 O69 1.234(10) . ?
C69 C69A 1.518(12) . ?
C69A C70 1.552(11) . ?
C69A H69A 1.0000 . ?
C70 C79 1.510(12) . ?
C70 C71 1.555(12) . ?
C70 H70 1.0000 . ?
C71 C80 1.501(12) . ?
C71 C72 1.527(12) . ?
C71 H71 1.0000 . ?
C72 O72 1.194(11) . ?
C72 C72A 1.497(12) . ?
C72A H72A 1.0000 . ?
C73 C78 1.370(12) . ?
C73 C74 1.432(12) . ?
C74 C75 1.391(13) . ?
C74 H74 0.9500 . ?
C75 C76 1.379(14) . ?
C75 H75 0.9500 . ?
C76 C77 1.388(14) . ?
C76 H76 0.9500 . ?
C77 C78 1.370(13) . ?
C77 H77 0.9500 . ?
C78 H78 0.9500 . ?
C79 O79 1.226(12) . ?
C79 O80 1.318(11) . ?
O79 H79 0.9000 . ?
O80 H80 0.9000 . ?
C80 C81 1.514(14) . ?
C80 H80A 0.9900 . ?
C80 H80B 0.9900 . ?
C81 O81 1.213(13) . ?
C81 C82 1.496(16) . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
S4 O4 1.501(3) . ?
S4 C84 1.765(3) . ?
S4 C83 1.771(3) . ?
C83 H83A 0.9800 . ?
C83 H83B 0.9800 . ?
C83 H83C 0.9800 . ?
C84 H84A 0.9800 . ?
C84 H84B 0.9800 . ?
C84 H84C 0.9800 . ?
S4' O4' 1.501(4) . ?
S4' C84' 1.771(4) . ?
S4' C83' 1.771(4) . ?
C83' H83D 0.9800 . ?
C83' H83E 0.9800 . ?
C83' H83F 0.9800 . ?
C84' H84D 0.9800 . ?
C84' H84E 0.9800 . ?
C84' H84F 0.9800 . ?
S4" O4" 1.500(4) . ?
S4" C84" 1.770(4) . ?
S4" C83" 1.771(4) . ?
C83" H83G 0.9800 . ?
C83" H83H 0.9800 . ?
C83" H83I 0.9800 . ?
C84" H84G 0.9800 . ?
C84" H84H 0.9800 . ?
C84" H84I 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
C9A C1 C2 105.6(7) . . ?
C9A C1 H1A 110.6 . . ?
C2 C1 H1A 110.6 . . ?
C9A C1 H1B 110.6 . . ?
C2 C1 H1B 110.6 . . ?
H1A C1 H1B 108.8 . . ?
C3 C2 C1 105.1(7) . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C3A C3 C2 103.8(7) . . ?
C3A C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C3A C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C3A C4 113.0(7) . . ?
C3 C3A C6A 117.8(7) . . ?
C4 C3A C6A 102.2(7) . . ?
C3 C3A C9A 101.9(7) . . ?
C4 C3A C9A 108.8(7) . . ?
C6A C3A C9A 113.3(6) . . ?
N5 C4 C3A 104.5(7) . . ?
N5 C4 H4A 110.9 . . ?
C3A C4 H4A 110.9 . . ?
N5 C4 H4B 110.9 . . ?
C3A C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C6 N5 C10 129.0(8) . . ?
C6 N5 C4 110.0(7) . . ?
C10 N5 C4 120.4(8) . . ?
O6 C6 N5 124.6(9) . . ?
O6 C6 C6A 125.7(8) . . ?
N5 C6 C6A 109.6(7) . . ?
C6 C6A C3A 103.4(7) . . ?
C6 C6A C7 114.2(7) . . ?
C3A C6A C7 117.3(7) . . ?
C6 C6A H6A 107.1 . . ?
C3A C6A H6A 107.1 . . ?
C7 C6A H6A 107.1 . . ?
C16 C7 C8 113.7(6) . . ?
C16 C7 C6A 110.5(7) . . ?
C8 C7 C6A 112.1(7) . . ?
C16 C7 H7 106.7 . . ?
C8 C7 H7 106.7 . . ?
C6A C7 H7 106.7 . . ?
C17 C8 C7 114.1(7) . . ?
C17 C8 C9 109.5(7) . . ?
C7 C8 C9 108.0(6) . . ?
C17 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
O9 C9 C9A 125.2(8) . . ?
O9 C9 C8 120.5(8) . . ?
C9A C9 C8 114.3(7) . . ?
C9 C9A C1 111.6(7) . . ?
C9 C9A C3A 110.9(7) . . ?
C1 C9A C3A 104.8(6) . . ?
C9 C9A H9A 109.8 . . ?
C1 C9A H9A 109.8 . . ?
C3A C9A H9A 109.8 . . ?
C15 C10 C11 119.1(10) . . ?
C15 C10 N5 120.5(9) . . ?
C11 C10 N5 120.4(10) . . ?
C12 C11 C10 119.6(12) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.4(12) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.2(12) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.3(13) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 121.0(11) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
O17 C16 O16 124.0(8) . . ?
O17 C16 C7 125.8(7) . . ?
O16 C16 C7 110.2(6) . . ?
C16 O16 H16 109.4 . . ?
C18 C17 C8 112.1(8) . . ?
C18 C17 H17A 109.2 . . ?
C8 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C8 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
O18 C18 C19 122.9(9) . . ?
O18 C18 C17 122.4(8) . . ?
C19 C18 C17 114.7(8) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 S1 C20 106.7(5) . . ?
O1 S1 C21 105.6(5) . . ?
C20 S1 C21 97.1(6) . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C30A C22 C23 105.7(7) . . ?
C30A C22 H22A 110.6 . . ?
C23 C22 H22A 110.6 . . ?
C30A C22 H22B 110.6 . . ?
C23 C22 H22B 110.6 . . ?
H22A C22 H22B 108.7 . . ?
C24 C23 C22 106.1(7) . . ?
C24 C23 H23A 110.5 . . ?
C22 C23 H23A 110.5 . . ?
C24 C23 H23B 110.5 . . ?
C22 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
C23 C24 C24A 104.3(7) . . ?
C23 C24 H24A 110.9 . . ?
C24A C24 H24A 110.9 . . ?
C23 C24 H24B 110.9 . . ?
C24A C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
C25 C24A C27A 103.9(7) . . ?
C25 C24A C24 111.4(6) . . ?
C27A C24A C24 116.0(7) . . ?
C25 C24A C30A 109.5(7) . . ?
C27A C24A C30A 115.3(6) . . ?
C24 C24A C30A 100.8(6) . . ?
N26 C25 C24A 102.7(7) . . ?
N26 C25 H25A 111.2 . . ?
C24A C25 H25A 111.2 . . ?
N26 C25 H25B 111.2 . . ?
C24A C25 H25B 111.2 . . ?
H25A C25 H25B 109.1 . . ?
C27 N26 C31 126.4(9) . . ?
C27 N26 C25 112.0(7) . . ?
C31 N26 C25 121.1(9) . . ?
O27 C27 N26 125.7(8) . . ?
O27 C27 C27A 126.4(8) . . ?
N26 C27 C27A 107.8(7) . . ?
C24A C27A C27 102.4(7) . . ?
C24A C27A C28 117.0(6) . . ?
C27 C27A C28 114.4(6) . . ?
C24A C27A H27A 107.5 . . ?
C27 C27A H27A 107.5 . . ?
C28 C27A H27A 107.5 . . ?
C37 C28 C27A 110.9(7) . . ?
C37 C28 C29 112.9(6) . . ?
C27A C28 C29 112.7(7) . . ?
C37 C28 H28 106.6 . . ?
C27A C28 H28 106.6 . . ?
C29 C28 H28 106.6 . . ?
C38 C29 C30 109.3(7) . . ?
C38 C29 C28 115.8(7) . . ?
C30 C29 C28 107.0(6) . . ?
C38 C29 H29 108.2 . . ?
C30 C29 H29 108.2 . . ?
C28 C29 H29 108.2 . . ?
O30 C30 C29 122.1(8) . . ?
O30 C30 C30A 123.2(7) . . ?
C29 C30 C30A 114.8(7) . . ?
C30 C30A C22 114.0(7) . . ?
C30 C30A C24A 110.8(7) . . ?
C22 C30A C24A 105.2(6) . . ?
C30 C30A H30A 108.9 . . ?
C22 C30A H30A 108.9 . . ?
C24A C30A H30A 108.9 . . ?
C32 C31 N26 121.7(13) . . ?
C32 C31 C36 119.2(12) . . ?
N26 C31 C36 119.0(12) . . ?
C31 C32 C33 119.5(15) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C32 C33 C34 120.8(14) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C35 C34 C33 119.8(12) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.6(15) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C31 120.2(14) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
O38 C37 O37 123.9(8) . . ?
O38 C37 C28 125.2(7) . . ?
O37 C37 C28 110.9(7) . . ?
C37 O37 H37 110.1 . . ?
C39 C38 C29 112.9(7) . . ?
C39 C38 H38A 109.0 . . ?
C29 C38 H38A 109.0 . . ?
C39 C38 H38B 109.0 . . ?
C29 C38 H38B 109.0 . . ?
H38A C38 H38B 107.8 . . ?
O39 C39 C38 124.3(9) . . ?
O39 C39 C40 119.7(8) . . ?
C38 C39 C40 115.9(8) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O2 S2 C41 105.8(5) . . ?
O2 S2 C42 106.4(5) . . ?
C41 S2 C42 98.1(7) . . ?
S2 C41 H41A 109.5 . . ?
S2 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
S2 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
S2 C42 H42A 109.5 . . ?
S2 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
S2 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C51A 105.7(8) . . ?
C44 C43 H43A 110.6 . . ?
C51A C43 H43A 110.6 . . ?
C44 C43 H43B 110.6 . . ?
C51A C43 H43B 110.6 . . ?
H43A C43 H43B 108.7 . . ?
C43 C44 C45 106.1(7) . . ?
C43 C44 H44A 110.5 . . ?
C45 C44 H44A 110.5 . . ?
C43 C44 H44B 110.5 . . ?
C45 C44 H44B 110.5 . . ?
H44A C44 H44B 108.7 . . ?
C45A C45 C44 102.2(8) . . ?
C45A C45 H45A 111.3 . . ?
C44 C45 H45A 111.3 . . ?
C45A C45 H45B 111.3 . . ?
C44 C45 H45B 111.3 . . ?
H45A C45 H45B 109.2 . . ?
C51A C45A C45 103.9(7) . . ?
C51A C45A C48A 114.6(7) . . ?
C45 C45A C48A 117.4(7) . . ?
C51A C45A C46 110.2(7) . . ?
C45 C45A C46 111.0(7) . . ?
C48A C45A C46 99.8(7) . . ?
N47 C46 C45A 103.2(6) . . ?
N47 C46 H46A 111.1 . . ?
C45A C46 H46A 111.1 . . ?
N47 C46 H46B 111.1 . . ?
C45A C46 H46B 111.1 . . ?
H46A C46 H46B 109.1 . . ?
C48 N47 C52 124.6(7) . . ?
C48 N47 C46 111.0(7) . . ?
C52 N47 C46 123.4(6) . . ?
O48 C48 N47 126.9(8) . . ?
O48 C48 C48A 125.5(7) . . ?
N47 C48 C48A 107.5(7) . . ?
C48 C48A C49 114.0(6) . . ?
C48 C48A C45A 103.9(6) . . ?
C49 C48A C45A 115.0(7) . . ?
C48 C48A H48A 107.9 . . ?
C49 C48A H48A 107.9 . . ?
C45A C48A H48A 107.9 . . ?
C58 C49 C48A 108.5(7) . . ?
C58 C49 C50 114.4(7) . . ?
C48A C49 C50 112.3(7) . . ?
C58 C49 H49 107.1 . . ?
C48A C49 H49 107.1 . . ?
C50 C49 H49 107.1 . . ?
C59 C50 C51 109.5(7) . . ?
C59 C50 C49 114.5(7) . . ?
C51 C50 C49 106.1(7) . . ?
C59 C50 H50 108.9 . . ?
C51 C50 H50 108.9 . . ?
C49 C50 H50 108.9 . . ?
O51 C51 C51A 124.6(8) . . ?
O51 C51 C50 121.0(8) . . ?
C51A C51 C50 114.4(7) . . ?
C51 C51A C45A 108.8(7) . . ?
C51 C51A C43 112.8(7) . . ?
C45A C51A C43 104.0(7) . . ?
C51 C51A H51A 110.3 . . ?
C45A C51A H51A 110.3 . . ?
C43 C51A H51A 110.3 . . ?
C53 C52 N47 123.1(7) . . ?
C53 C52 C57 118.1(8) . . ?
N47 C52 C57 118.8(7) . . ?
C54 C53 C52 121.2(8) . . ?
C54 C53 H53 119.4 . . ?
C52 C53 H53 119.4 . . ?
C55 C54 C53 120.2(8) . . ?
C55 C54 H54 119.9 . . ?
C53 C54 H54 119.9 . . ?
C54 C55 C56 118.9(8) . . ?
C54 C55 H55 120.5 . . ?
C56 C55 H55 120.5 . . ?
C57 C56 C55 122.3(8) . . ?
C57 C56 H56 118.9 . . ?
C55 C56 H56 118.9 . . ?
C56 C57 C52 119.2(8) . . ?
C56 C57 H57 120.4 . . ?
C52 C57 H57 120.4 . . ?
O58 C58 O59 122.4(7) . . ?
O58 C58 C49 118.9(8) . . ?
O59 C58 C49 118.8(8) . . ?
C58 O58 H58 109.6 . . ?
C58 O59 H59 109.4 . . ?
C50 C59 C60 112.9(8) . . ?
C50 C59 H59A 109.0 . . ?
C60 C59 H59A 109.0 . . ?
C50 C59 H59B 109.0 . . ?
C60 C59 H59B 109.0 . . ?
H59A C59 H59B 107.8 . . ?
O60 C60 C61 124.0(9) . . ?
O60 C60 C59 120.5(9) . . ?
C61 C60 C59 115.4(8) . . ?
C60 C61 H61A 109.5 . . ?
C60 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C60 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
O3 S3 C63 106.5(3) . . ?
O3 S3 C62 106.8(3) . . ?
C63 S3 C62 96.1(2) . . ?
S3 C62 H62A 109.5 . . ?
S3 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
S3 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
S3 C63 H63A 109.5 . . ?
S3 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
S3 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
O3' S3' C63' 106.5(3) . . ?
O3' S3' C62' 106.5(3) . . ?
C63' S3' C62' 95.9(3) . . ?
S3' C62' H62D 109.5 . . ?
S3' C62' H62E 109.5 . . ?
H62D C62' H62E 109.5 . . ?
S3' C62' H62F 109.5 . . ?
H62D C62' H62F 109.5 . . ?
H62E C62' H62F 109.5 . . ?
S3' C63' H63D 109.5 . . ?
S3' C63' H63E 109.5 . . ?
H63D C63' H63E 109.5 . . ?
S3' C63' H63F 109.5 . . ?
H63D C63' H63F 109.5 . . ?
H63E C63' H63F 109.5 . . ?
C72A C64 C65 104.3(8) . . ?
C72A C64 H64A 110.9 . . ?
C65 C64 H64A 110.9 . . ?
C72A C64 H64B 110.9 . . ?
C65 C64 H64B 110.9 . . ?
H64A C64 H64B 108.9 . . ?
C66 C65 C64 107.7(8) . . ?
C66 C65 H65A 110.2 . . ?
C64 C65 H65A 110.2 . . ?
C66 C65 H65B 110.2 . . ?
C64 C65 H65B 110.2 . . ?
H65A C65 H65B 108.5 . . ?
C65 C66 C66A 104.1(7) . . ?
C65 C66 H66A 110.9 . . ?
C66A C66 H66A 110.9 . . ?
C65 C66 H66B 110.9 . . ?
C66A C66 H66B 110.9 . . ?
H66A C66 H66B 108.9 . . ?
C69A C66A C67 101.9(7) . . ?
C69A C66A C66 119.0(7) . . ?
C67 C66A C66 113.0(7) . . ?
C69A C66A C72A 113.5(7) . . ?
C67 C66A C72A 109.1(7) . . ?
C66 C66A C72A 100.4(7) . . ?
N68 C67 C66A 102.7(7) . . ?
N68 C67 H67A 111.2 . . ?
C66A C67 H67A 111.2 . . ?
N68 C67 H67B 111.2 . . ?
C66A C67 H67B 111.2 . . ?
H67A C67 H67B 109.1 . . ?
C69 N68 C73 127.9(7) . . ?
C69 N68 C67 111.0(7) . . ?
C73 N68 C67 120.5(7) . . ?
O69 C69 N68 126.7(8) . . ?
O69 C69 C69A 124.6(7) . . ?
N68 C69 C69A 108.5(7) . . ?
C66A C69A C69 102.3(7) . . ?
C66A C69A C70 117.1(7) . . ?
C69 C69A C70 113.6(7) . . ?
C66A C69A H69A 107.8 . . ?
C69 C69A H69A 107.8 . . ?
C70 C69A H69A 107.8 . . ?
C79 C70 C69A 108.6(7) . . ?
C79 C70 C71 115.9(7) . . ?
C69A C70 C71 111.6(7) . . ?
C79 C70 H70 106.7 . . ?
C69A C70 H70 106.7 . . ?
C71 C70 H70 106.7 . . ?
C80 C71 C72 110.9(7) . . ?
C80 C71 C70 114.8(7) . . ?
C72 C71 C70 107.1(7) . . ?
C80 C71 H71 108.0 . . ?
C72 C71 H71 108.0 . . ?
C70 C71 H71 108.0 . . ?
O72 C72 C72A 123.8(8) . . ?
O72 C72 C71 119.8(8) . . ?
C72A C72 C71 116.4(7) . . ?
C72 C72A C64 112.6(7) . . ?
C72 C72A C66A 109.7(7) . . ?
C64 C72A C66A 105.3(7) . . ?
C72 C72A H72A 109.7 . . ?
C64 C72A H72A 109.7 . . ?
C66A C72A H72A 109.7 . . ?
C78 C73 N68 121.1(8) . . ?
C78 C73 C74 118.6(8) . . ?
N68 C73 C74 120.2(7) . . ?
C75 C74 C73 118.9(8) . . ?
C75 C74 H74 120.5 . . ?
C73 C74 H74 120.5 . . ?
C76 C75 C74 121.0(9) . . ?
C76 C75 H75 119.5 . . ?
C74 C75 H75 119.5 . . ?
C75 C76 C77 119.2(8) . . ?
C75 C76 H76 120.4 . . ?
C77 C76 H76 120.4 . . ?
C78 C77 C76 120.7(8) . . ?
C78 C77 H77 119.7 . . ?
C76 C77 H77 119.7 . . ?
C77 C78 C73 121.5(9) . . ?
C77 C78 H78 119.2 . . ?
C73 C78 H78 119.2 . . ?
O79 C79 O80 124.2(8) . . ?
O79 C79 C70 120.2(8) . . ?
O80 C79 C70 115.6(8) . . ?
C79 O79 H79 109.5 . . ?
C79 O80 H80 109.0 . . ?
C71 C80 C81 112.0(8) . . ?
C71 C80 H80A 109.2 . . ?
C81 C80 H80A 109.2 . . ?
C71 C80 H80B 109.2 . . ?
C81 C80 H80B 109.2 . . ?
H80A C80 H80B 107.9 . . ?
O81 C81 C82 120.6(11) . . ?
O81 C81 C80 121.8(9) . . ?
C82 C81 C80 117.2(10) . . ?
C81 C82 H82A 109.5 . . ?
C81 C82 H82B 109.5 . . ?
H82A C82 H82B 109.5 . . ?
C81 C82 H82C 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
O4 S4 C84 107.1(3) . . ?
O4 S4 C83 106.6(3) . . ?
C84 S4 C83 96.3(2) . . ?
S4 C83 H83A 109.5 . . ?
S4 C83 H83B 109.5 . . ?
H83A C83 H83B 109.5 . . ?
S4 C83 H83C 109.5 . . ?
H83A C83 H83C 109.5 . . ?
H83B C83 H83C 109.5 . . ?
S4 C84 H84A 109.5 . . ?
S4 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
S4 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 109.5 . . ?
O4' S4' C84' 106.7(3) . . ?
O4' S4' C83' 106.7(3) . . ?
C84' S4' C83' 95.9(3) . . ?
S4' C83' H83D 109.5 . . ?
S4' C83' H83E 109.5 . . ?
H83D C83' H83E 109.5 . . ?
S4' C83' H83F 109.5 . . ?
H83D C83' H83F 109.5 . . ?
H83E C83' H83F 109.5 . . ?
S4' C84' H84D 109.5 . . ?
S4' C84' H84E 109.5 . . ?
H84D C84' H84E 109.5 . . ?
S4' C84' H84F 109.5 . . ?
H84D C84' H84F 109.5 . . ?
H84E C84' H84F 109.5 . . ?
O4" S4" C84" 106.8(3) . . ?
O4" S4" C83" 106.7(3) . . ?
C84" S4" C83" 95.9(3) . . ?
S4" C83" H83G 109.5 . . ?
S4" C83" H83H 109.5 . . ?
H83G C83" H83H 109.5 . . ?
S4" C83" H83I 109.5 . . ?
H83G C83" H83I 109.5 . . ?
H83H C83" H83I 109.5 . . ?
S4" C84" H84G 109.5 . . ?
S4" C84" H84H 109.5 . . ?
H84G C84" H84H 109.5 . . ?
S4" C84" H84I 109.5 . . ?
H84G C84" H84I 109.5 . . ?
H84H C84" H84I 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
C9A C1 C2 C3 -11.5(9) . . . . ?
C1 C2 C3 C3A 34.7(9) . . . . ?
C2 C3 C3A C4 72.9(9) . . . . ?
C2 C3 C3A C6A -168.3(7) . . . . ?
C2 C3 C3A C9A -43.7(8) . . . . ?
C3 C3A C4 N5 158.6(8) . . . . ?
C6A C3A C4 N5 31.0(9) . . . . ?
C9A C3A C4 N5 -89.0(8) . . . . ?
C3A C4 N5 C6 -20.8(10) . . . . ?
C3A C4 N5 C10 167.7(8) . . . . ?
C10 N5 C6 O6 -4.1(16) . . . . ?
C4 N5 C6 O6 -174.7(9) . . . . ?
C10 N5 C6 C6A 171.7(9) . . . . ?
C4 N5 C6 C6A 1.2(10) . . . . ?
O6 C6 C6A C3A -165.4(9) . . . . ?
N5 C6 C6A C3A 18.8(9) . . . . ?
O6 C6 C6A C7 -36.8(13) . . . . ?
N5 C6 C6A C7 147.4(8) . . . . ?
C3 C3A C6A C6 -154.4(7) . . . . ?
C4 C3A C6A C6 -29.9(8) . . . . ?
C9A C3A C6A C6 86.9(8) . . . . ?
C3 C3A C6A C7 79.0(9) . . . . ?
C4 C3A C6A C7 -156.6(7) . . . . ?
C9A C3A C6A C7 -39.8(10) . . . . ?
C6 C6A C7 C16 52.8(9) . . . . ?
C3A C6A C7 C16 174.0(7) . . . . ?
C6 C6A C7 C8 -75.1(9) . . . . ?
C3A C6A C7 C8 46.0(9) . . . . ?
C16 C7 C8 C17 57.9(10) . . . . ?
C6A C7 C8 C17 -175.8(7) . . . . ?
C16 C7 C8 C9 180.0(7) . . . . ?
C6A C7 C8 C9 -53.7(9) . . . . ?
C17 C8 C9 O9 7.0(11) . . . . ?
C7 C8 C9 O9 -117.8(9) . . . . ?
C17 C8 C9 C9A -173.3(7) . . . . ?
C7 C8 C9 C9A 61.9(9) . . . . ?
O9 C9 C9A C1 6.9(12) . . . . ?
C8 C9 C9A C1 -172.9(7) . . . . ?
O9 C9 C9A C3A 123.3(9) . . . . ?
C8 C9 C9A C3A -56.4(9) . . . . ?
C2 C1 C9A C9 105.1(8) . . . . ?
C2 C1 C9A C3A -15.0(9) . . . . ?
C3 C3A C9A C9 -84.4(8) . . . . ?
C4 C3A C9A C9 156.0(6) . . . . ?
C6A C3A C9A C9 43.2(9) . . . . ?
C3 C3A C9A C1 36.2(8) . . . . ?
C4 C3A C9A C1 -83.4(8) . . . . ?
C6A C3A C9A C1 163.8(7) . . . . ?
C6 N5 C10 C15 -145.4(11) . . . . ?
C4 N5 C10 C15 24.4(16) . . . . ?
C6 N5 C10 C11 35.8(16) . . . . ?
C4 N5 C10 C11 -154.5(10) . . . . ?
C15 C10 C11 C12 0.4(18) . . . . ?
N5 C10 C11 C12 179.3(11) . . . . ?
C10 C11 C12 C13 -3(2) . . . . ?
C11 C12 C13 C14 6(2) . . . . ?
C12 C13 C14 C15 -6(3) . . . . ?
C11 C10 C15 C14 -1(2) . . . . ?
N5 C10 C15 C14 -179.9(13) . . . . ?
C13 C14 C15 C10 4(3) . . . . ?
C8 C7 C16 O17 6.6(13) . . . . ?
C6A C7 C16 O17 -120.5(10) . . . . ?
C8 C7 C16 O16 -173.0(7) . . . . ?
C6A C7 C16 O16 59.9(9) . . . . ?
C7 C8 C17 C18 -173.7(7) . . . . ?
C9 C8 C17 C18 65.1(9) . . . . ?
C8 C17 C18 O18 17.2(13) . . . . ?
C8 C17 C18 C19 -163.9(8) . . . . ?
C30A C22 C23 C24 -6.8(9) . . . . ?
C22 C23 C24 C24A 30.7(9) . . . . ?
C23 C24 C24A C25 74.2(8) . . . . ?
C23 C24 C24A C27A -167.2(7) . . . . ?
C23 C24 C24A C30A -41.9(8) . . . . ?
C27A C24A C25 N26 31.6(8) . . . . ?
C24 C24A C25 N26 157.3(7) . . . . ?
C30A C24A C25 N26 -92.1(7) . . . . ?
C24A C25 N26 C27 -20.4(10) . . . . ?
C24A C25 N26 C31 166.6(9) . . . . ?
C31 N26 C27 O27 -3.6(16) . . . . ?
C25 N26 C27 O27 -176.2(9) . . . . ?
C31 N26 C27 C27A 172.8(10) . . . . ?
C25 N26 C27 C27A 0.2(10) . . . . ?
C25 C24A C27A C27 -31.5(8) . . . . ?
C24 C24A C27A C27 -154.2(7) . . . . ?
C30A C24A C27A C27 88.3(8) . . . . ?
C25 C24A C27A C28 -157.5(6) . . . . ?
C24 C24A C27A C28 79.8(8) . . . . ?
C30A C24A C27A C28 -37.6(9) . . . . ?
O27 C27 C27A C24A -163.9(9) . . . . ?
N26 C27 C27A C24A 19.8(9) . . . . ?
O27 C27 C27A C28 -36.3(13) . . . . ?
N26 C27 C27A C28 147.4(7) . . . . ?
C24A C27A C28 C37 173.7(6) . . . . ?
C27 C27A C28 C37 53.9(9) . . . . ?
C24A C27A C28 C29 46.0(9) . . . . ?
C27 C27A C28 C29 -73.8(9) . . . . ?
C37 C28 C29 C38 56.2(9) . . . . ?
C27A C28 C29 C38 -177.2(7) . . . . ?
C37 C28 C29 C30 178.2(7) . . . . ?
C27A C28 C29 C30 -55.2(8) . . . . ?
C38 C29 C30 O30 8.2(11) . . . . ?
C28 C29 C30 O30 -117.8(9) . . . . ?
C38 C29 C30 C30A -172.4(6) . . . . ?
C28 C29 C30 C30A 61.6(8) . . . . ?
O30 C30 C30A C22 6.9(11) . . . . ?
C29 C30 C30A C22 -172.5(7) . . . . ?
O30 C30 C30A C24A 125.3(8) . . . . ?
C29 C30 C30A C24A -54.0(8) . . . . ?
C23 C22 C30A C30 102.1(8) . . . . ?
C23 C22 C30A C24A -19.5(9) . . . . ?
C25 C24A C30A C30 156.4(6) . . . . ?
C27A C24A C30A C30 39.7(9) . . . . ?
C24 C24A C30A C30 -86.0(7) . . . . ?
C25 C24A C30A C22 -80.0(8) . . . . ?
C27A C24A C30A C22 163.3(7) . . . . ?
C24 C24A C30A C22 37.6(8) . . . . ?
C27 N26 C31 C32 33.5(17) . . . . ?
C25 N26 C31 C32 -154.6(10) . . . . ?
C27 N26 C31 C36 -150.3(11) . . . . ?
C25 N26 C31 C36 21.6(16) . . . . ?
N26 C31 C32 C33 176.9(11) . . . . ?
C36 C31 C32 C33 0.7(19) . . . . ?
C31 C32 C33 C34 -0.7(19) . . . . ?
C32 C33 C34 C35 0.8(19) . . . . ?
C33 C34 C35 C36 -1.0(19) . . . . ?
C34 C35 C36 C31 1.0(19) . . . . ?
C32 C31 C36 C35 -0.8(19) . . . . ?
N26 C31 C36 C35 -177.1(11) . . . . ?
C27A C28 C37 O38 -119.1(9) . . . . ?
C29 C28 C37 O38 8.5(13) . . . . ?
C27A C28 C37 O37 62.0(9) . . . . ?
C29 C28 C37 O37 -170.5(7) . . . . ?
C30 C29 C38 C39 66.4(9) . . . . ?
C28 C29 C38 C39 -172.8(7) . . . . ?
C29 C38 C39 O39 16.2(13) . . . . ?
C29 C38 C39 C40 -160.7(8) . . . . ?
C51A C43 C44 C45 8.7(10) . . . . ?
C43 C44 C45 C45A -31.4(10) . . . . ?
C44 C45 C45A C51A 42.6(9) . . . . ?
C44 C45 C45A C48A 170.3(8) . . . . ?
C44 C45 C45A C46 -75.8(9) . . . . ?
C51A C45A C46 N47 84.8(8) . . . . ?
C45 C45A C46 N47 -160.7(7) . . . . ?
C48A C45A C46 N47 -36.2(8) . . . . ?
C45A C46 N47 C48 25.4(9) . . . . ?
C45A C46 N47 C52 -165.2(7) . . . . ?
C52 N47 C48 O48 5.9(12) . . . . ?
C46 N47 C48 O48 175.2(8) . . . . ?
C52 N47 C48 C48A -171.8(7) . . . . ?
C46 N47 C48 C48A -2.5(9) . . . . ?
O48 C48 C48A C49 34.9(11) . . . . ?
N47 C48 C48A C49 -147.3(7) . . . . ?
O48 C48 C48A C45A 160.8(7) . . . . ?
N47 C48 C48A C45A -21.4(8) . . . . ?
C51A C45A C48A C48 -82.8(8) . . . . ?
C45 C45A C48A C48 154.9(7) . . . . ?
C46 C45A C48A C48 34.9(8) . . . . ?
C51A C45A C48A C49 42.5(10) . . . . ?
C45 C45A C48A C49 -79.9(9) . . . . ?
C46 C45A C48A C49 160.2(7) . . . . ?
C48 C48A C49 C58 -54.8(9) . . . . ?
C45A C48A C49 C58 -174.6(7) . . . . ?
C48 C48A C49 C50 72.7(9) . . . . ?
C45A C48A C49 C50 -47.2(9) . . . . ?
C58 C49 C50 C59 -59.5(10) . . . . ?
C48A C49 C50 C59 176.2(7) . . . . ?
C58 C49 C50 C51 179.5(7) . . . . ?
C48A C49 C50 C51 55.3(9) . . . . ?
C59 C50 C51 O51 -10.5(11) . . . . ?
C49 C50 C51 O51 113.6(9) . . . . ?
C59 C50 C51 C51A 171.6(7) . . . . ?
C49 C50 C51 C51A -64.4(9) . . . . ?
O51 C51 C51A C45A -117.8(9) . . . . ?
C50 C51 C51A C45A 60.0(9) . . . . ?
O51 C51 C51A C43 -2.9(12) . . . . ?
C50 C51 C51A C43 174.9(7) . . . . ?
C45 C45A C51A C51 83.0(8) . . . . ?
C48A C45A C51A C51 -46.4(10) . . . . ?
C46 C45A C51A C51 -158.0(7) . . . . ?
C45 C45A C51A C43 -37.5(9) . . . . ?
C48A C45A C51A C43 -166.9(7) . . . . ?
C46 C45A C51A C43 81.5(8) . . . . ?
C44 C43 C51A C51 -100.3(9) . . . . ?
C44 C43 C51A C45A 17.5(9) . . . . ?
C48 N47 C52 C53 -28.2(12) . . . . ?
C46 N47 C52 C53 163.8(8) . . . . ?
C48 N47 C52 C57 152.0(8) . . . . ?
C46 N47 C52 C57 -16.0(12) . . . . ?
N47 C52 C53 C54 178.9(8) . . . . ?
C57 C52 C53 C54 -1.3(13) . . . . ?
C52 C53 C54 C55 1.8(14) . . . . ?
C53 C54 C55 C56 -1.7(14) . . . . ?
C54 C55 C56 C57 1.2(14) . . . . ?
C55 C56 C57 C52 -0.8(14) . . . . ?
C53 C52 C57 C56 0.8(13) . . . . ?
N47 C52 C57 C56 -179.4(8) . . . . ?
C48A C49 C58 O58 -57.7(10) . . . . ?
C50 C49 C58 O58 176.0(7) . . . . ?
C48A C49 C58 O59 121.6(8) . . . . ?
C50 C49 C58 O59 -4.6(11) . . . . ?
C51 C50 C59 C60 -76.8(9) . . . . ?
C49 C50 C59 C60 164.2(7) . . . . ?
C50 C59 C60 O60 -4.4(14) . . . . ?
C50 C59 C60 C61 179.1(8) . . . . ?
C72A C64 C65 C66 7.6(11) . . . . ?
C64 C65 C66 C66A -31.5(10) . . . . ?
C65 C66 C66A C69A 166.6(8) . . . . ?
C65 C66 C66A C67 -73.9(10) . . . . ?
C65 C66 C66A C72A 42.1(9) . . . . ?
C69A C66A C67 N68 -34.7(8) . . . . ?
C66 C66A C67 N68 -163.6(7) . . . . ?
C72A C66A C67 N68 85.5(8) . . . . ?
C66A C67 N68 C69 22.1(9) . . . . ?
C66A C67 N68 C73 -165.6(7) . . . . ?
C73 N68 C69 O69 4.6(14) . . . . ?
C67 N68 C69 O69 176.2(8) . . . . ?
C73 N68 C69 C69A -171.5(8) . . . . ?
C67 N68 C69 C69A 0.1(10) . . . . ?
C67 C66A C69A C69 34.4(8) . . . . ?
C66 C66A C69A C69 159.5(8) . . . . ?
C72A C66A C69A C69 -82.7(8) . . . . ?
C67 C66A C69A C70 159.3(7) . . . . ?
C66 C66A C69A C70 -75.6(10) . . . . ?
C72A C66A C69A C70 42.2(10) . . . . ?
O69 C69 C69A C66A 161.2(8) . . . . ?
N68 C69 C69A C66A -22.6(9) . . . . ?
O69 C69 C69A C70 34.0(12) . . . . ?
N68 C69 C69A C70 -149.8(7) . . . . ?
C66A C69A C70 C79 -176.5(7) . . . . ?
C69 C69A C70 C79 -57.5(9) . . . . ?
C66A C69A C70 C71 -47.5(10) . . . . ?
C69 C69A C70 C71 71.5(9) . . . . ?
C79 C70 C71 C80 -58.7(10) . . . . ?
C69A C70 C71 C80 176.3(7) . . . . ?
C79 C70 C71 C72 177.8(7) . . . . ?
C69A C70 C71 C72 52.8(9) . . . . ?
C80 C71 C72 O72 -11.3(12) . . . . ?
C70 C71 C72 O72 114.6(9) . . . . ?
C80 C71 C72 C72A 172.5(8) . . . . ?
C70 C71 C72 C72A -61.6(9) . . . . ?
O72 C72 C72A C64 -2.4(13) . . . . ?
C71 C72 C72A C64 173.6(8) . . . . ?
O72 C72 C72A C66A -119.4(9) . . . . ?
C71 C72 C72A C66A 56.7(9) . . . . ?
C65 C64 C72A C72 -100.3(9) . . . . ?
C65 C64 C72A C66A 19.2(9) . . . . ?
C69A C66A C72A C72 -44.1(9) . . . . ?
C67 C66A C72A C72 -156.9(7) . . . . ?
C66 C66A C72A C72 84.1(8) . . . . ?
C69A C66A C72A C64 -165.5(7) . . . . ?
C67 C66A C72A C64 81.7(8) . . . . ?
C66 C66A C72A C64 -37.3(8) . . . . ?
C69 N68 C73 C78 156.1(9) . . . . ?
C67 N68 C73 C78 -14.8(13) . . . . ?
C69 N68 C73 C74 -21.1(13) . . . . ?
C67 N68 C73 C74 168.0(8) . . . . ?
C78 C73 C74 C75 1.3(13) . . . . ?
N68 C73 C74 C75 178.6(8) . . . . ?
C73 C74 C75 C76 -0.9(14) . . . . ?
C74 C75 C76 C77 1.5(14) . . . . ?
C75 C76 C77 C78 -2.4(14) . . . . ?
C76 C77 C78 C73 2.9(15) . . . . ?
N68 C73 C78 C77 -179.6(9) . . . . ?
C74 C73 C78 C77 -2.3(14) . . . . ?
C69A C70 C79 O79 -58.3(10) . . . . ?
C71 C70 C79 O79 175.1(7) . . . . ?
C69A C70 C79 O80 122.6(8) . . . . ?
C71 C70 C79 O80 -3.9(10) . . . . ?
C72 C71 C80 C81 -66.9(10) . . . . ?
C70 C71 C80 C81 171.6(7) . . . . ?
C71 C80 C81 O81 -21.1(13) . . . . ?
C71 C80 C81 C82 166.6(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O16 H16 O1 0.90 1.68 2.561(9) 165.9 .
O37 H37 O2 0.90 1.70 2.575(9) 164.8 1_655
O58 H58 O3' 0.90 1.71 2.606(16) 177.6 1_565
O59 H59 O3 0.90 1.60 2.483(10) 166.8 1_565
O79 H79 O4' 0.90 1.53 2.42(3) 168.8 1_545
O80 H80 O4 0.90 1.64 2.500(10) 159.3 1_545

_refine_diff_density_max         0.789
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-4


# start Validation Reply Form
_vrf_PLAT340_12c                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0137 Ang.  
RESPONSE: The single-crystal was of very low quality.
;
_vrf_PLAT915_12c                 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         29 %     
RESPONSE: This is due to the most low symmetry of the crystal structure.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_zv1763
_database_code_depnum_ccdc_archive 'CCDC 2495036'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 D6 F3 N O5 S'
_chemical_formula_weight         499.52

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1549(7)
_cell_length_b                   16.3136(13)
_cell_length_c                   16.7975(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.219(5)
_cell_angle_gamma                90
_cell_volume                     2233.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9002
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      24.20

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'TWINABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38520
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.234
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             14240
_reflns_number_gt                11435
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.804
_reflns_Friedel_fraction_full    0.896

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.9523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         14240
_refine_ls_number_parameters     622
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.6488(4) 0.4143(2) 0.3012(2) 0.0304(9) Uani 1 1 d . . . . .
F2 F 0.4865(4) 0.5129(2) 0.3324(2) 0.0329(8) Uani 1 1 d . . . . .
F3 F 0.4805(4) 0.3986(2) 0.3953(2) 0.0311(8) Uani 1 1 d . . . . .
O1 O 0.6264(5) 0.6691(3) 0.3962(3) 0.0291(10) Uani 1 1 d . . . . .
O2 O 0.5028(5) 0.5119(3) 0.5136(3) 0.0340(11) Uani 1 1 d . . . . .
O3 O 0.7576(5) 0.5592(3) 0.5385(3) 0.0290(10) Uani 1 1 d . . . . .
H3 H 0.718203 0.577704 0.580309 0.035 Uiso 1 1 calc R U . . .
O5 O 1.0242(5) 0.3305(2) 0.3730(3) 0.0263(10) Uani 1 1 d . . . . .
N2 N 0.9019(6) 0.6877(3) 0.3752(3) 0.0224(11) Uani 1 1 d . . . . .
C1 C 0.7623(7) 0.6432(4) 0.3857(3) 0.0217(13) Uani 1 1 d . . . . .
C3 C 1.0431(7) 0.6362(4) 0.3554(4) 0.0229(13) Uani 1 1 d . . . . .
H3A H 1.147182 0.658178 0.378950 0.027 Uiso 1 1 calc R U . . .
H3B H 1.052512 0.630461 0.297053 0.027 Uiso 1 1 calc R U . . .
C3A C 0.9967(7) 0.5551(4) 0.3939(4) 0.0239(13) Uani 1 1 d . . . . .
H3AA H 1.016402 0.559802 0.452824 0.029 Uiso 1 1 calc R U . . .
C4 C 1.0715(7) 0.4763(4) 0.3664(4) 0.0239(13) Uani 1 1 d . . . . .
H4A H 1.166615 0.473011 0.335563 0.029 Uiso 1 1 calc R U . . .
C4A C 0.9874(7) 0.4118(4) 0.3907(3) 0.0230(13) Uani 1 1 d . . . . .
C5A C 0.9085(7) 0.2818(4) 0.4098(4) 0.0234(13) Uani 1 1 d . . . . .
C6 C 0.9072(8) 0.1980(4) 0.4055(4) 0.0271(14) Uani 1 1 d . . . . .
H6A H 0.986549 0.168462 0.377012 0.033 Uiso 1 1 calc R U . . .
C7 C 0.7824(8) 0.1583(4) 0.4453(4) 0.0275(15) Uani 1 1 d . . . . .
H7A H 0.774562 0.100247 0.443223 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6704(8) 0.2023(4) 0.4877(4) 0.0278(15) Uani 1 1 d . . . . .
H8A H 0.587799 0.173597 0.514745 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6750(7) 0.2880(4) 0.4920(4) 0.0246(14) Uani 1 1 d . . . . .
H9A H 0.598804 0.317657 0.522150 0.029 Uiso 1 1 calc R U . . .
C9A C 0.7950(7) 0.3278(4) 0.4505(4) 0.0216(13) Uani 1 1 d . . . . .
C9B C 0.8442(7) 0.4171(4) 0.4452(4) 0.0231(13) Uani 1 1 d . . . . .
H9BA H 0.891151 0.432637 0.498951 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7156(7) 0.4859(4) 0.4205(4) 0.0231(13) Uani 1 1 d . . . . .
C10A C 0.8110(7) 0.5532(4) 0.3756(4) 0.0215(13) Uani 1 1 d . . . . .
H10A H 0.795945 0.540573 0.317515 0.026 Uiso 1 1 calc R U . . .
C11 C 0.6423(7) 0.5211(4) 0.4962(4) 0.0256(14) Uani 1 1 d . . . . .
C12 C 0.5832(7) 0.4524(4) 0.3632(4) 0.0271(14) Uani 1 1 d . . . . .
C13 C 0.9071(7) 0.7744(4) 0.3723(4) 0.0224(13) Uani 1 1 d . . . . .
C14 C 0.8134(8) 0.8208(4) 0.4228(4) 0.0315(15) Uani 1 1 d . . . . .
H14A H 0.747073 0.794422 0.460372 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8167(7) 0.9067(4) 0.4181(4) 0.0265(14) Uani 1 1 d . . . . .
H15A H 0.750931 0.938584 0.451831 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9157(8) 0.9446(4) 0.3646(4) 0.0309(15) Uani 1 1 d . . . . .
H16A H 0.917753 1.002755 0.361134 0.037 Uiso 1 1 calc R U . . .
C17 C 1.0115(8) 0.8982(4) 0.3162(4) 0.0315(15) Uani 1 1 d . . . . .
H17A H 1.082166 0.924934 0.280725 0.038 Uiso 1 1 calc R U . . .
C18 C 1.0070(7) 0.8134(4) 0.3181(4) 0.0268(14) Uani 1 1 d . . . . .
H18A H 1.070838 0.782145 0.283024 0.032 Uiso 1 1 calc R U . . .
F21 F 0.6575(5) 0.5880(3) 0.1890(2) 0.0455(11) Uani 1 1 d . . . . .
F22 F 0.4974(4) 0.4884(3) 0.1495(2) 0.0454(11) Uani 1 1 d . . . . .
F23 F 0.4943(4) 0.6020(2) 0.0859(2) 0.0398(10) Uani 1 1 d . . . . .
O21 O 0.6377(5) 0.3318(3) 0.0921(3) 0.0365(12) Uani 1 1 d . . . . .
O22 O 0.5208(6) 0.4844(3) -0.0281(3) 0.0387(12) Uani 1 1 d . . . . .
O23 O 0.7814(5) 0.4447(3) -0.0442(3) 0.0335(11) Uani 1 1 d . . . . .
H23 H 0.742564 0.425305 -0.087255 0.040 Uiso 1 1 calc R U . . .
O25 O 1.0419(6) 0.6697(3) 0.1357(3) 0.0325(11) Uani 1 1 d . . . . .
N22 N 0.9123(6) 0.3125(3) 0.1289(3) 0.0297(13) Uani 1 1 d . . . . .
C21 C 0.7725(9) 0.3584(4) 0.1106(4) 0.0307(16) Uani 1 1 d . . . . .
C23 C 1.0510(8) 0.3635(4) 0.1560(4) 0.0277(14) Uani 1 1 d . . . . .
H23A H 1.156358 0.340865 0.138398 0.033 Uiso 1 1 calc R U . . .
H23B H 1.055997 0.369331 0.214666 0.033 Uiso 1 1 calc R U . . .
C23A C 1.0102(7) 0.4446(4) 0.1150(4) 0.0276(15) Uani 1 1 d . . . . .
H23C H 1.033618 0.439470 0.057197 0.033 Uiso 1 1 calc R U . . .
C24 C 1.0826(7) 0.5232(4) 0.1457(4) 0.0278(14) Uani 1 1 d . . . . .
H24A H 1.174744 0.526221 0.181978 0.033 Uiso 1 1 calc R U . . .
C24A C 1.0035(8) 0.5879(4) 0.1167(4) 0.0293(15) Uani 1 1 d . . . . .
C25A C 0.9266(8) 0.7176(4) 0.0944(4) 0.0320(16) Uani 1 1 d . . . . .
C26 C 0.9269(9) 0.8025(4) 0.0986(4) 0.0367(17) Uani 1 1 d . . . . .
H26A H 1.003999 0.831470 0.131733 0.044 Uiso 1 1 calc R U . . .
C27 C 0.8093(9) 0.8424(4) 0.0520(4) 0.0383(18) Uani 1 1 d . . . . .
H27A H 0.807097 0.900654 0.051696 0.046 Uiso 1 1 calc R U . . .
C28 C 0.6942(8) 0.7997(4) 0.0056(4) 0.0320(16) Uani 1 1 d . . . . .
H28A H 0.612601 0.828949 -0.024672 0.038 Uiso 1 1 calc R U . . .
C29 C 0.6968(8) 0.7148(4) 0.0029(4) 0.0334(16) Uani 1 1 d . . . . .
H29A H 0.618907 0.685294 -0.029373 0.040 Uiso 1 1 calc R U . . .
C29A C 0.8153(8) 0.6746(4) 0.0482(4) 0.0273(14) Uani 1 1 d . . . . .
C29B C 0.8604(8) 0.5842(4) 0.0569(4) 0.0311(16) Uani 1 1 d . . . . .
H29B H 0.908348 0.568316 0.005244 0.037 Uiso 1 1 calc R U . . .
C30 C 0.7315(7) 0.5153(4) 0.0751(4) 0.0259(14) Uani 1 1 d . . . . .
C30A C 0.8229(7) 0.4466(4) 0.1235(4) 0.0250(14) Uani 1 1 d . . . . .
H30A H 0.804894 0.458651 0.180930 0.030 Uiso 1 1 calc R U . . .
C31 C 0.6617(8) 0.4794(4) -0.0044(4) 0.0259(14) Uani 1 1 d . . . . .
C32 C 0.5916(8) 0.5479(5) 0.1233(4) 0.0362(17) Uani 1 1 d . . . . .
C33 C 0.9113(7) 0.2263(4) 0.1333(4) 0.0255(14) Uani 1 1 d . . . . .
C34 C 0.8212(8) 0.1790(5) 0.0779(4) 0.0340(16) Uani 1 1 d . . . . .
H34A H 0.759757 0.204907 0.035816 0.041 Uiso 1 1 calc R U . . .
C35 C 0.8212(7) 0.0947(4) 0.0842(4) 0.0307(15) Uani 1 1 d . . . . .
H35A H 0.758720 0.062781 0.046711 0.037 Uiso 1 1 calc R U . . .
C36 C 0.9122(8) 0.0562(4) 0.1451(4) 0.0337(16) Uani 1 1 d . . . . .
H36A H 0.911733 -0.001851 0.149331 0.040 Uiso 1 1 calc R U . . .
C37 C 1.0025(8) 0.1024(4) 0.1991(4) 0.0322(16) Uani 1 1 d . . . . .
H37A H 1.064377 0.075951 0.240788 0.039 Uiso 1 1 calc R U . . .
C38 C 1.0046(8) 0.1871(4) 0.1937(4) 0.0296(15) Uani 1 1 d . . . . .
H38A H 1.069124 0.218479 0.230833 0.036 Uiso 1 1 calc R U . . .
S1 S 0.5166(2) 0.61998(11) 0.70843(9) 0.0330(4) Uani 1 1 d . . . . .
O41 O 0.6821(5) 0.6250(3) 0.6696(2) 0.0338(11) Uani 1 1 d . . . . .
C41 C 0.5671(9) 0.5911(6) 0.8092(5) 0.052(2) Uani 1 1 d . . . . .
D41A D 0.466236 0.586479 0.838812 0.077 Uiso 1 1 calc R U . . .
D41B D 0.624076 0.538237 0.809866 0.077 Uiso 1 1 calc R U . . .
D41C D 0.638512 0.632878 0.834209 0.077 Uiso 1 1 calc R U . . .
C42 C 0.4605(10) 0.7235(5) 0.7269(5) 0.052(2) Uani 1 1 d . . . . .
D42A D 0.354158 0.724741 0.752150 0.078 Uiso 1 1 calc R U . . .
D42B D 0.543914 0.749066 0.762402 0.078 Uiso 1 1 calc R U . . .
D42C D 0.452570 0.753592 0.676460 0.078 Uiso 1 1 calc R U . . .
S2A S 0.5556(3) 0.3186(2) -0.17500(18) 0.0413(12) Uani 0.651(7) 1 d . . P A 1
O42 O 0.6994(5) 0.3796(3) -0.1776(3) 0.0397(12) Uani 1 1 d . . . . .
C43 C 0.3958(17) 0.3740(8) -0.2270(8) 0.050(3) Uiso 0.651(7) 1 d . . P A 1
D43A D 0.295483 0.340899 -0.229403 0.076 Uiso 0.651(7) 1 calc R U P A 1
D43B D 0.375211 0.425445 -0.198942 0.076 Uiso 0.651(7) 1 calc R U P A 1
D43C D 0.429058 0.386108 -0.281206 0.076 Uiso 0.651(7) 1 calc R U P A 1
C44 C 0.5947(15) 0.2414(7) -0.2463(7) 0.046(3) Uiso 0.651(7) 1 d . . P A 1
D44A D 0.505910 0.200901 -0.246897 0.068 Uiso 0.651(7) 1 calc R U P A 1
D44B D 0.600604 0.266361 -0.299198 0.068 Uiso 0.651(7) 1 calc R U P A 1
D44C D 0.699106 0.214353 -0.232215 0.068 Uiso 0.651(7) 1 calc R U P A 1
S2B S 0.5253(11) 0.3724(4) -0.2152(4) 0.067(3) Uani 0.349(7) 1 d . . P A 2
C45 C 0.546(3) 0.3877(19) -0.3157(17) 0.072(8) Uiso 0.349(7) 1 d . . P A 2
D45A D 0.438182 0.383864 -0.343269 0.108 Uiso 0.349(7) 1 calc R U P A 2
D45B D 0.592747 0.442155 -0.324564 0.108 Uiso 0.349(7) 1 calc R U P A 2
D45C D 0.619049 0.345793 -0.336551 0.108 Uiso 0.349(7) 1 calc R U P A 2
C46 C 0.492(4) 0.266(2) -0.211(2) 0.098(11) Uiso 0.349(7) 1 d . . P A 2
D46A D 0.382113 0.253621 -0.233471 0.147 Uiso 0.349(7) 1 calc R U P A 2
D46B D 0.574545 0.237813 -0.241095 0.147 Uiso 0.349(7) 1 calc R U P A 2
D46C D 0.499474 0.248245 -0.155054 0.147 Uiso 0.349(7) 1 calc R 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
F1 C12 1.341(7) . ?
F2 C12 1.354(7) . ?
F3 C12 1.340(7) . ?
O1 C1 1.206(6) . ?
O2 C11 1.195(6) . ?
O3 C11 1.313(8) . ?
O3 H3 0.8400 . ?
O5 C4A 1.395(7) . ?
O5 C5A 1.396(7) . ?
N2 C1 1.367(7) . ?
N2 C13 1.416(8) . ?
N2 C3 1.474(7) . ?
C1 C10A 1.532(8) . ?
C3 C3A 1.527(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.503(8) . ?
C3A C10A 1.534(8) . ?
C3A H3AA 1.0000 . ?
C4 C4A 1.329(8) . ?
C4 H4A 0.9500 . ?
C4A C9B 1.513(8) . ?
C5A C6 1.370(9) . ?
C5A C9A 1.391(8) . ?
C6 C7 1.398(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.381(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.400(9) . ?
C8 H8A 0.9500 . ?
C9 C9A 1.384(9) . ?
C9 H9A 0.9500 . ?
C9A C9B 1.515(8) . ?
C9B C10 1.581(8) . ?
C9B H9BA 1.0000 . ?
C10 C12 1.520(9) . ?
C10 C11 1.537(9) . ?
C10 C10A 1.557(8) . ?
C10A H10A 1.0000 . ?
C13 C14 1.387(9) . ?
C13 C18 1.398(8) . ?
C14 C15 1.404(9) . ?
C14 H14A 0.9500 . ?
C15 C16 1.378(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.377(9) . ?
C16 H16A 0.9500 . ?
C17 C18 1.384(9) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
F21 C32 1.374(8) . ?
F22 C32 1.324(8) . ?
F23 C32 1.328(7) . ?
O21 C21 1.211(7) . ?
O22 C31 1.204(7) . ?
O23 C31 1.330(7) . ?
O23 H23 0.8400 . ?
O25 C25A 1.387(8) . ?
O25 C24A 1.405(8) . ?
N22 C21 1.388(8) . ?
N22 C33 1.408(8) . ?
N22 C23 1.462(8) . ?
C21 C30A 1.510(9) . ?
C23 C23A 1.523(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23A C24 1.495(9) . ?
C23A C30A 1.541(8) . ?
C23A H23C 1.0000 . ?
C24 C24A 1.321(9) . ?
C24 H24A 0.9500 . ?
C24A C29B 1.511(9) . ?
C25A C29A 1.365(9) . ?
C25A C26 1.386(9) . ?
C26 C27 1.378(10) . ?
C26 H26A 0.9500 . ?
C27 C28 1.384(9) . ?
C27 H27A 0.9500 . ?
C28 C29 1.387(9) . ?
C28 H28A 0.9500 . ?
C29 C29A 1.374(9) . ?
C29 H29A 0.9500 . ?
C29A C29B 1.525(9) . ?
C29B C30 1.578(9) . ?
C29B H29B 1.0000 . ?
C30 C32 1.520(9) . ?
C30 C31 1.547(9) . ?
C30 C30A 1.557(9) . ?
C30A H30A 1.0000 . ?
C33 C34 1.395(9) . ?
C33 C38 1.400(9) . ?
C34 C35 1.379(10) . ?
C34 H34A 0.9500 . ?
C35 C36 1.390(9) . ?
C35 H35A 0.9500 . ?
C36 C37 1.372(9) . ?
C36 H36A 0.9500 . ?
C37 C38 1.385(9) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?
S1 O41 1.524(4) . ?
S1 C42 1.780(7) . ?
S1 C41 1.790(8) . ?
C41 D41A 0.9800 . ?
C41 D41B 0.9800 . ?
C41 D41C 0.9800 . ?
C42 D42A 0.9800 . ?
C42 D42B 0.9800 . ?
C42 D42C 0.9800 . ?
S2A O42 1.540(6) . ?
S2A C44 1.776(12) . ?
S2A C43 1.786(14) . ?
O42 S2B 1.536(8) . ?
C43 D43A 0.9800 . ?
C43 D43B 0.9800 . ?
C43 D43C 0.9800 . ?
C44 D44A 0.9800 . ?
C44 D44B 0.9800 . ?
C44 D44C 0.9800 . ?
S2B C45 1.72(3) . ?
S2B C46 1.76(4) . ?
C45 D45A 0.9800 . ?
C45 D45B 0.9800 . ?
C45 D45C 0.9800 . ?
C46 D46A 0.9800 . ?
C46 D46B 0.9800 . ?
C46 D46C 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
C11 O3 H3 109.5 . . ?
C4A O5 C5A 107.0(4) . . ?
C1 N2 C13 124.1(5) . . ?
C1 N2 C3 112.8(5) . . ?
C13 N2 C3 122.5(5) . . ?
O1 C1 N2 127.4(6) . . ?
O1 C1 C10A 126.6(5) . . ?
N2 C1 C10A 105.9(5) . . ?
N2 C3 C3A 101.0(4) . . ?
N2 C3 H3A 111.6 . . ?
C3A C3 H3A 111.6 . . ?
N2 C3 H3B 111.6 . . ?
C3A C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
C4 C3A C3 120.0(5) . . ?
C4 C3A C10A 109.3(5) . . ?
C3 C3A C10A 101.0(5) . . ?
C4 C3A H3AA 108.6 . . ?
C3 C3A H3AA 108.6 . . ?
C10A C3A H3AA 108.6 . . ?
C4A C4 C3A 111.2(5) . . ?
C4A C4 H4A 124.4 . . ?
C3A C4 H4A 124.4 . . ?
C4 C4A O5 124.7(5) . . ?
C4 C4A C9B 124.1(5) . . ?
O5 C4A C9B 111.1(5) . . ?
C6 C5A C9A 124.1(6) . . ?
C6 C5A O5 123.2(5) . . ?
C9A C5A O5 112.7(5) . . ?
C5A C6 C7 116.1(6) . . ?
C5A C6 H6A 121.9 . . ?
C7 C6 H6A 121.9 . . ?
C8 C7 C6 121.0(6) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C9 121.9(6) . . ?
C7 C8 H8A 119.1 . . ?
C9 C8 H8A 119.1 . . ?
C9A C9 C8 117.4(6) . . ?
C9A C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
C9 C9A C5A 119.4(6) . . ?
C9 C9A C9B 132.5(5) . . ?
C5A C9A C9B 107.8(5) . . ?
C4A C9B C9A 101.2(5) . . ?
C4A C9B C10 113.7(5) . . ?
C9A C9B C10 121.6(5) . . ?
C4A C9B H9BA 106.5 . . ?
C9A C9B H9BA 106.5 . . ?
C10 C9B H9BA 106.5 . . ?
C12 C10 C11 111.6(5) . . ?
C12 C10 C10A 107.7(5) . . ?
C11 C10 C10A 110.8(5) . . ?
C12 C10 C9B 111.0(5) . . ?
C11 C10 C9B 108.9(5) . . ?
C10A C10 C9B 106.8(4) . . ?
C1 C10A C3A 102.5(5) . . ?
C1 C10A C10 119.0(5) . . ?
C3A C10A C10 115.2(5) . . ?
C1 C10A H10A 106.4 . . ?
C3A C10A H10A 106.4 . . ?
C10 C10A H10A 106.4 . . ?
O2 C11 O3 126.5(6) . . ?
O2 C11 C10 124.1(6) . . ?
O3 C11 C10 109.3(5) . . ?
F3 C12 F1 106.4(5) . . ?
F3 C12 F2 105.5(5) . . ?
F1 C12 F2 106.5(5) . . ?
F3 C12 C10 114.9(5) . . ?
F1 C12 C10 111.3(5) . . ?
F2 C12 C10 111.6(5) . . ?
C14 C13 C18 119.9(6) . . ?
C14 C13 N2 120.4(5) . . ?
C18 C13 N2 119.7(5) . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C16 C15 C14 119.8(6) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C17 C16 C15 119.9(6) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C18 121.3(6) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C17 C18 C13 119.1(6) . . ?
C17 C18 H18A 120.4 . . ?
C13 C18 H18A 120.4 . . ?
C31 O23 H23 109.5 . . ?
C25A O25 C24A 106.3(5) . . ?
C21 N22 C33 123.0(6) . . ?
C21 N22 C23 112.4(6) . . ?
C33 N22 C23 123.9(5) . . ?
O21 C21 N22 126.4(7) . . ?
O21 C21 C30A 128.1(6) . . ?
N22 C21 C30A 105.4(6) . . ?
N22 C23 C23A 101.6(5) . . ?
N22 C23 H23A 111.5 . . ?
C23A C23 H23A 111.5 . . ?
N22 C23 H23B 111.5 . . ?
C23A C23 H23B 111.5 . . ?
H23A C23 H23B 109.3 . . ?
C24 C23A C23 120.9(5) . . ?
C24 C23A C30A 109.2(5) . . ?
C23 C23A C30A 100.2(5) . . ?
C24 C23A H23C 108.6 . . ?
C23 C23A H23C 108.6 . . ?
C30A C23A H23C 108.6 . . ?
C24A C24 C23A 112.2(6) . . ?
C24A C24 H24A 123.9 . . ?
C23A C24 H24A 123.9 . . ?
C24 C24A O25 125.1(6) . . ?
C24 C24A C29B 124.6(6) . . ?
O25 C24A C29B 110.4(5) . . ?
C29A C25A C26 122.9(6) . . ?
C29A C25A O25 114.6(6) . . ?
C26 C25A O25 122.5(6) . . ?
C27 C26 C25A 116.3(6) . . ?
C27 C26 H26A 121.8 . . ?
C25A C26 H26A 121.8 . . ?
C26 C27 C28 121.5(6) . . ?
C26 C27 H27A 119.2 . . ?
C28 C27 H27A 119.2 . . ?
C27 C28 C29 120.7(6) . . ?
C27 C28 H28A 119.7 . . ?
C29 C28 H28A 119.7 . . ?
C29A C29 C28 118.1(6) . . ?
C29A C29 H29A 121.0 . . ?
C28 C29 H29A 121.0 . . ?
C25A C29A C29 120.5(6) . . ?
C25A C29A C29B 106.9(6) . . ?
C29 C29A C29B 132.6(6) . . ?
C24A C29B C29A 101.7(5) . . ?
C24A C29B C30 113.8(5) . . ?
C29A C29B C30 123.2(6) . . ?
C24A C29B H29B 105.6 . . ?
C29A C29B H29B 105.6 . . ?
C30 C29B H29B 105.6 . . ?
C32 C30 C31 109.5(5) . . ?
C32 C30 C30A 109.1(5) . . ?
C31 C30 C30A 109.3(5) . . ?
C32 C30 C29B 111.9(6) . . ?
C31 C30 C29B 109.1(5) . . ?
C30A C30 C29B 107.8(5) . . ?
C21 C30A C23A 103.4(5) . . ?
C21 C30A C30 119.2(5) . . ?
C23A C30A C30 115.0(5) . . ?
C21 C30A H30A 106.1 . . ?
C23A C30A H30A 106.1 . . ?
C30 C30A H30A 106.1 . . ?
O22 C31 O23 124.9(6) . . ?
O22 C31 C30 125.0(6) . . ?
O23 C31 C30 110.0(5) . . ?
F22 C32 F23 107.5(5) . . ?
F22 C32 F21 107.2(6) . . ?
F23 C32 F21 105.8(6) . . ?
F22 C32 C30 112.2(6) . . ?
F23 C32 C30 115.3(6) . . ?
F21 C32 C30 108.4(5) . . ?
C34 C33 C38 119.2(6) . . ?
C34 C33 N22 121.5(6) . . ?
C38 C33 N22 119.3(6) . . ?
C35 C34 C33 120.1(6) . . ?
C35 C34 H34A 119.9 . . ?
C33 C34 H34A 119.9 . . ?
C34 C35 C36 120.3(6) . . ?
C34 C35 H35A 119.8 . . ?
C36 C35 H35A 119.8 . . ?
C37 C36 C35 119.8(6) . . ?
C37 C36 H36A 120.1 . . ?
C35 C36 H36A 120.1 . . ?
C36 C37 C38 120.8(6) . . ?
C36 C37 H37A 119.6 . . ?
C38 C37 H37A 119.6 . . ?
C37 C38 C33 119.7(6) . . ?
C37 C38 H38A 120.1 . . ?
C33 C38 H38A 120.1 . . ?
O41 S1 C42 105.2(3) . . ?
O41 S1 C41 104.2(3) . . ?
C42 S1 C41 97.8(4) . . ?
S1 C41 D41A 109.5 . . ?
S1 C41 D41B 109.5 . . ?
D41A C41 D41B 109.5 . . ?
S1 C41 D41C 109.5 . . ?
D41A C41 D41C 109.5 . . ?
D41B C41 D41C 109.5 . . ?
S1 C42 D42A 109.5 . . ?
S1 C42 D42B 109.5 . . ?
D42A C42 D42B 109.5 . . ?
S1 C42 D42C 109.5 . . ?
D42A C42 D42C 109.5 . . ?
D42B C42 D42C 109.5 . . ?
O42 S2A C44 106.4(5) . . ?
O42 S2A C43 101.6(5) . . ?
C44 S2A C43 100.1(6) . . ?
S2A C43 D43A 109.5 . . ?
S2A C43 D43B 109.5 . . ?
D43A C43 D43B 109.5 . . ?
S2A C43 D43C 109.5 . . ?
D43A C43 D43C 109.5 . . ?
D43B C43 D43C 109.5 . . ?
S2A C44 D44A 109.5 . . ?
S2A C44 D44B 109.5 . . ?
D44A C44 D44B 109.5 . . ?
S2A C44 D44C 109.5 . . ?
D44A C44 D44C 109.5 . . ?
D44B C44 D44C 109.5 . . ?
O42 S2B C45 105.6(10) . . ?
O42 S2B C46 101.6(12) . . ?
C45 S2B C46 101.9(17) . . ?
S2B C45 D45A 109.5 . . ?
S2B C45 D45B 109.5 . . ?
D45A C45 D45B 109.5 . . ?
S2B C45 D45C 109.5 . . ?
D45A C45 D45C 109.5 . . ?
D45B C45 D45C 109.5 . . ?
S2B C46 D46A 109.5 . . ?
S2B C46 D46B 109.5 . . ?
D46A C46 D46B 109.5 . . ?
S2B C46 D46C 109.5 . . ?
D46A C46 D46C 109.5 . . ?
D46B C46 D46C 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
C13 N2 C1 O1 -2.2(9) . . . . ?
C3 N2 C1 O1 -173.9(6) . . . . ?
C13 N2 C1 C10A 173.9(5) . . . . ?
C3 N2 C1 C10A 2.3(6) . . . . ?
C1 N2 C3 C3A -26.5(6) . . . . ?
C13 N2 C3 C3A 161.7(5) . . . . ?
N2 C3 C3A C4 158.7(5) . . . . ?
N2 C3 C3A C10A 38.5(6) . . . . ?
C3 C3A C4 C4A -163.7(6) . . . . ?
C10A C3A C4 C4A -47.8(7) . . . . ?
C3A C4 C4A O5 178.4(5) . . . . ?
C3A C4 C4A C9B -5.1(8) . . . . ?
C5A O5 C4A C4 179.6(6) . . . . ?
C5A O5 C4A C9B 2.7(6) . . . . ?
C4A O5 C5A C6 -179.8(6) . . . . ?
C4A O5 C5A C9A 0.7(7) . . . . ?
C9A C5A C6 C7 -0.2(10) . . . . ?
O5 C5A C6 C7 -179.7(5) . . . . ?
C5A C6 C7 C8 -1.3(9) . . . . ?
C6 C7 C8 C9 0.8(10) . . . . ?
C7 C8 C9 C9A 1.3(10) . . . . ?
C8 C9 C9A C5A -2.7(9) . . . . ?
C8 C9 C9A C9B -175.5(6) . . . . ?
C6 C5A C9A C9 2.3(10) . . . . ?
O5 C5A C9A C9 -178.2(5) . . . . ?
C6 C5A C9A C9B 176.7(6) . . . . ?
O5 C5A C9A C9B -3.8(7) . . . . ?
C4 C4A C9B C9A 178.5(6) . . . . ?
O5 C4A C9B C9A -4.7(6) . . . . ?
C4 C4A C9B C10 46.5(8) . . . . ?
O5 C4A C9B C10 -136.7(5) . . . . ?
C9 C9A C9B C4A 178.3(7) . . . . ?
C5A C9A C9B C4A 4.9(6) . . . . ?
C9 C9A C9B C10 -54.7(10) . . . . ?
C5A C9A C9B C10 131.9(6) . . . . ?
C4A C9B C10 C12 89.9(6) . . . . ?
C9A C9B C10 C12 -31.3(7) . . . . ?
C4A C9B C10 C11 -146.8(5) . . . . ?
C9A C9B C10 C11 92.0(7) . . . . ?
C4A C9B C10 C10A -27.1(7) . . . . ?
C9A C9B C10 C10A -148.3(5) . . . . ?
O1 C1 C10A C3A -160.9(6) . . . . ?
N2 C1 C10A C3A 22.9(6) . . . . ?
O1 C1 C10A C10 -32.5(9) . . . . ?
N2 C1 C10A C10 151.4(5) . . . . ?
C4 C3A C10A C1 -165.4(5) . . . . ?
C3 C3A C10A C1 -37.9(6) . . . . ?
C4 C3A C10A C10 63.7(7) . . . . ?
C3 C3A C10A C10 -168.8(5) . . . . ?
C12 C10 C10A C1 96.0(6) . . . . ?
C11 C10 C10A C1 -26.3(7) . . . . ?
C9B C10 C10A C1 -144.8(5) . . . . ?
C12 C10 C10A C3A -141.7(5) . . . . ?
C11 C10 C10A C3A 96.0(6) . . . . ?
C9B C10 C10A C3A -22.4(7) . . . . ?
C12 C10 C11 O2 10.9(8) . . . . ?
C10A C10 C11 O2 130.9(6) . . . . ?
C9B C10 C11 O2 -112.0(6) . . . . ?
C12 C10 C11 O3 -171.4(5) . . . . ?
C10A C10 C11 O3 -51.4(6) . . . . ?
C9B C10 C11 O3 65.7(6) . . . . ?
C11 C10 C12 F3 -52.6(7) . . . . ?
C10A C10 C12 F3 -174.4(5) . . . . ?
C9B C10 C12 F3 69.1(6) . . . . ?
C11 C10 C12 F1 -173.7(5) . . . . ?
C10A C10 C12 F1 64.5(6) . . . . ?
C9B C10 C12 F1 -52.0(6) . . . . ?
C11 C10 C12 F2 67.5(6) . . . . ?
C10A C10 C12 F2 -54.3(6) . . . . ?
C9B C10 C12 F2 -170.8(5) . . . . ?
C1 N2 C13 C14 39.1(9) . . . . ?
C3 N2 C13 C14 -150.1(6) . . . . ?
C1 N2 C13 C18 -140.7(6) . . . . ?
C3 N2 C13 C18 30.2(8) . . . . ?
C18 C13 C14 C15 1.2(10) . . . . ?
N2 C13 C14 C15 -178.5(5) . . . . ?
C13 C14 C15 C16 -1.3(10) . . . . ?
C14 C15 C16 C17 -0.3(10) . . . . ?
C15 C16 C17 C18 2.1(10) . . . . ?
C16 C17 C18 C13 -2.2(10) . . . . ?
C14 C13 C18 C17 0.5(9) . . . . ?
N2 C13 C18 C17 -179.7(5) . . . . ?
C33 N22 C21 O21 -4.2(11) . . . . ?
C23 N22 C21 O21 -174.6(6) . . . . ?
C33 N22 C21 C30A 172.3(6) . . . . ?
C23 N22 C21 C30A 2.0(7) . . . . ?
C21 N22 C23 C23A -26.7(7) . . . . ?
C33 N22 C23 C23A 163.0(6) . . . . ?
N22 C23 C23A C24 158.5(6) . . . . ?
N22 C23 C23A C30A 38.7(6) . . . . ?
C23 C23A C24 C24A -163.8(6) . . . . ?
C30A C23A C24 C24A -48.6(7) . . . . ?
C23A C24 C24A O25 179.0(6) . . . . ?
C23A C24 C24A C29B -2.1(9) . . . . ?
C25A O25 C24A C24 -178.2(6) . . . . ?
C25A O25 C24A C29B 2.8(7) . . . . ?
C24A O25 C25A C29A -0.9(8) . . . . ?
C24A O25 C25A C26 -179.7(6) . . . . ?
C29A C25A C26 C27 -1.2(11) . . . . ?
O25 C25A C26 C27 177.5(6) . . . . ?
C25A C26 C27 C28 2.0(11) . . . . ?
C26 C27 C28 C29 -1.8(12) . . . . ?
C27 C28 C29 C29A 0.8(11) . . . . ?
C26 C25A C29A C29 0.2(11) . . . . ?
O25 C25A C29A C29 -178.6(6) . . . . ?
C26 C25A C29A C29B 177.5(6) . . . . ?
O25 C25A C29A C29B -1.3(8) . . . . ?
C28 C29 C29A C25A 0.0(10) . . . . ?
C28 C29 C29A C29B -176.5(7) . . . . ?
C24 C24A C29B C29A 177.6(6) . . . . ?
O25 C24A C29B C29A -3.4(7) . . . . ?
C24 C24A C29B C30 43.0(9) . . . . ?
O25 C24A C29B C30 -138.0(6) . . . . ?
C25A C29A C29B C24A 2.7(7) . . . . ?
C29 C29A C29B C24A 179.5(7) . . . . ?
C25A C29A C29B C30 131.5(6) . . . . ?
C29 C29A C29B C30 -51.6(11) . . . . ?
C24A C29B C30 C32 94.0(6) . . . . ?
C29A C29B C30 C32 -29.6(8) . . . . ?
C24A C29B C30 C31 -144.7(5) . . . . ?
C29A C29B C30 C31 91.8(7) . . . . ?
C24A C29B C30 C30A -26.0(7) . . . . ?
C29A C29B C30 C30A -149.6(6) . . . . ?
O21 C21 C30A C23A -160.1(7) . . . . ?
N22 C21 C30A C23A 23.4(6) . . . . ?
O21 C21 C30A C30 -31.0(10) . . . . ?
N22 C21 C30A C30 152.5(5) . . . . ?
C24 C23A C30A C21 -166.3(5) . . . . ?
C23 C23A C30A C21 -38.4(6) . . . . ?
C24 C23A C30A C30 62.0(7) . . . . ?
C23 C23A C30A C30 -170.1(5) . . . . ?
C32 C30 C30A C21 93.1(7) . . . . ?
C31 C30 C30A C21 -26.6(8) . . . . ?
C29B C30 C30A C21 -145.1(6) . . . . ?
C32 C30 C30A C23A -143.2(6) . . . . ?
C31 C30 C30A C23A 97.0(6) . . . . ?
C29B C30 C30A C23A -21.5(7) . . . . ?
C32 C30 C31 O22 7.2(9) . . . . ?
C30A C30 C31 O22 126.8(6) . . . . ?
C29B C30 C31 O22 -115.6(7) . . . . ?
C32 C30 C31 O23 -175.0(5) . . . . ?
C30A C30 C31 O23 -55.4(6) . . . . ?
C29B C30 C31 O23 62.2(6) . . . . ?
C31 C30 C32 F22 68.8(7) . . . . ?
C30A C30 C32 F22 -50.8(7) . . . . ?
C29B C30 C32 F22 -170.0(5) . . . . ?
C31 C30 C32 F23 -54.7(8) . . . . ?
C30A C30 C32 F23 -174.3(5) . . . . ?
C29B C30 C32 F23 66.5(8) . . . . ?
C31 C30 C32 F21 -173.0(5) . . . . ?
C30A C30 C32 F21 67.4(7) . . . . ?
C29B C30 C32 F21 -51.8(7) . . . . ?
C21 N22 C33 C34 41.0(9) . . . . ?
C23 N22 C33 C34 -149.8(6) . . . . ?
C21 N22 C33 C38 -139.9(6) . . . . ?
C23 N22 C33 C38 29.3(9) . . . . ?
C38 C33 C34 C35 1.6(10) . . . . ?
N22 C33 C34 C35 -179.3(6) . . . . ?
C33 C34 C35 C36 -0.7(10) . . . . ?
C34 C35 C36 C37 -0.1(10) . . . . ?
C35 C36 C37 C38 -0.1(10) . . . . ?
C36 C37 C38 C33 1.1(10) . . . . ?
C34 C33 C38 C37 -1.9(10) . . . . ?
N22 C33 C38 C37 179.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O41 0.84 1.72 2.546(6) 166.7 . yes
O23 H23 O42 0.84 1.71 2.545(6) 169.4 . yes

_refine_diff_density_max         0.735
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.062


# start Validation Reply Form
_vrf_PLAT910_zv1763              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 23 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_ZV2253
_database_code_depnum_ccdc_archive 'CCDC 2495038'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.3473(8)
_cell_length_b                   8.0310(5)
_cell_length_c                   16.2960(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.882(2)
_cell_angle_gamma                90
_cell_volume                     1604.29(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5030
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      29.40

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26484
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.183
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4675
_reflns_number_gt                3448
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.3168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4675
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38095(7) 0.37688(11) 0.37066(6) 0.0159(2) Uani 1 1 d . . . . .
O2 O 0.51490(8) 0.08562(12) 0.30293(6) 0.0177(2) Uani 1 1 d . . . . .
O3 O 0.65492(8) 0.13724(12) 0.23020(6) 0.0165(2) Uani 1 1 d . . . . .
H3 H 0.6326(18) 0.042(3) 0.2036(14) 0.057(7) Uiso 1 1 d . . . . .
O5 O 0.90603(7) 0.35688(12) 0.44537(6) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.44229(9) 0.24125(13) 0.49252(6) 0.0119(2) Uani 1 1 d . . . . .
C1 C 0.45537(10) 0.32015(15) 0.41994(8) 0.0118(2) Uani 1 1 d . . . . .
C3 C 0.54762(10) 0.20792(16) 0.54347(8) 0.0135(2) Uani 1 1 d . . . . .
H3A H 0.547789 0.096767 0.569749 0.016 Uiso 1 1 calc R U . . .
H3B H 0.563615 0.293616 0.586899 0.016 Uiso 1 1 calc R U . . .
C3A C 0.62922(10) 0.21577(15) 0.48048(8) 0.0122(2) Uani 1 1 d . . . . .
H3C H 0.631405 0.104586 0.453101 0.015 Uiso 1 1 calc R U . . .
C4 C 0.74585(11) 0.26809(17) 0.51160(8) 0.0157(3) Uani 1 1 d . . . . .
H4A H 0.745805 0.361422 0.551280 0.019 Uiso 1 1 calc R U . . .
H4B H 0.786793 0.173749 0.539403 0.019 Uiso 1 1 calc R U . . .
C4A C 0.79602(10) 0.32069(16) 0.43704(8) 0.0142(3) Uani 1 1 d . . . . .
C5A C 0.92677(11) 0.41083(16) 0.36811(8) 0.0154(3) Uani 1 1 d . . . . .
C6 C 1.02651(11) 0.46889(17) 0.34896(9) 0.0194(3) Uani 1 1 d . . . . .
H6A H 1.089539 0.470526 0.388595 0.023 Uiso 1 1 calc R U . . .
C7 C 1.02896(12) 0.52448(18) 0.26851(9) 0.0220(3) Uani 1 1 d . . . . .
H7A H 1.095295 0.565943 0.252381 0.026 Uiso 1 1 calc R U . . .
C8 C 0.93540(12) 0.52052(18) 0.21072(9) 0.0215(3) Uani 1 1 d . . . . .
H8A H 0.939657 0.559723 0.156193 0.026 Uiso 1 1 calc R U . . .
C9 C 0.83649(11) 0.46066(17) 0.23117(9) 0.0177(3) Uani 1 1 d . . . . .
H9A H 0.773681 0.457424 0.191358 0.021 Uiso 1 1 calc R U . . .
C9A C 0.83212(11) 0.40532(15) 0.31207(8) 0.0139(3) Uani 1 1 d . . . . .
C9B C 0.74738(10) 0.34623(15) 0.35889(8) 0.0119(2) Uani 1 1 d . . . . .
C10 C 0.62555(10) 0.33048(15) 0.33561(8) 0.0117(2) Uani 1 1 d . . . . .
H10B H 0.599424 0.427681 0.300304 0.014 Uiso 1 1 calc R U . . .
C10A C 0.57653(10) 0.34133(15) 0.41710(7) 0.0111(2) Uani 1 1 d . . . . .
H10A H 0.595659 0.454278 0.440293 0.013 Uiso 1 1 calc R U . . .
C11 C 0.59185(10) 0.17067(15) 0.28914(8) 0.0126(2) Uani 1 1 d . . . . .
C12 C 0.34206(10) 0.22438(15) 0.52749(8) 0.0128(2) Uani 1 1 d . . . . .
C13 C 0.24280(11) 0.20822(16) 0.47763(8) 0.0172(3) Uani 1 1 d . . . . .
H13A H 0.240145 0.209594 0.419132 0.021 Uiso 1 1 calc R U . . .
C14 C 0.14737(12) 0.19001(18) 0.51471(9) 0.0224(3) Uani 1 1 d . . . . .
H14A H 0.079409 0.179645 0.480988 0.027 Uiso 1 1 calc R U . . .
C15 C 0.15014(12) 0.18678(18) 0.60017(9) 0.0227(3) Uani 1 1 d . . . . .
H15A H 0.084568 0.174324 0.624682 0.027 Uiso 1 1 calc R U . . .
C16 C 0.24897(12) 0.20181(17) 0.64929(9) 0.0197(3) Uani 1 1 d . . . . .
H16A H 0.251257 0.198967 0.707749 0.024 Uiso 1 1 calc R U . . .
C17 C 0.34516(12) 0.22110(15) 0.61367(8) 0.0160(3) Uani 1 1 d . . . . .
H17A H 0.412799 0.232013 0.647744 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2329(15) . ?
O2 C11 1.2128(15) . ?
O3 C11 1.3342(15) . ?
O5 C4A 1.3797(15) . ?
O5 C5A 1.3841(16) . ?
N2 C1 1.3684(16) . ?
N2 C12 1.4295(16) . ?
N2 C3 1.4811(16) . ?
C1 C10A 1.5118(17) . ?
C3 C3A 1.5233(18) . ?
C3A C4 1.5272(18) . ?
C3A C10A 1.5316(17) . ?
C4 C4A 1.4895(18) . ?
C4A C9B 1.3571(18) . ?
C5A C6 1.3870(18) . ?
C5A C9A 1.3950(19) . ?
C6 C7 1.389(2) . ?
C7 C8 1.401(2) . ?
C8 C9 1.3897(19) . ?
C9 C9A 1.3984(18) . ?
C9A C9B 1.4468(17) . ?
C9B C10 1.5119(18) . ?
C10 C11 1.5226(17) . ?
C10 C10A 1.5265(17) . ?
C12 C13 1.3930(19) . ?
C12 C17 1.4005(17) . ?
C13 C14 1.3949(19) . ?
C14 C15 1.389(2) . ?
C15 C16 1.382(2) . ?
C16 C17 1.3916(19) . ?

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
C4A O5 C5A 105.30(10) . . ?
C1 N2 C12 125.87(11) . . ?
C1 N2 C3 112.42(10) . . ?
C12 N2 C3 120.23(10) . . ?
O1 C1 N2 125.32(12) . . ?
O1 C1 C10A 126.98(11) . . ?
N2 C1 C10A 107.36(10) . . ?
N2 C3 C3A 102.83(10) . . ?
C3 C3A C4 117.46(11) . . ?
C3 C3A C10A 102.70(10) . . ?
C4 C3A C10A 110.50(10) . . ?
C4A C4 C3A 105.96(10) . . ?
C9B C4A O5 112.35(11) . . ?
C9B C4A C4 128.89(12) . . ?
O5 C4A C4 118.71(11) . . ?
O5 C5A C6 125.17(12) . . ?
O5 C5A C9A 110.71(11) . . ?
C6 C5A C9A 124.07(13) . . ?
C5A C6 C7 116.16(13) . . ?
C6 C7 C8 121.20(13) . . ?
C9 C8 C7 121.62(13) . . ?
C8 C9 C9A 118.06(13) . . ?
C5A C9A C9 118.89(12) . . ?
C5A C9A C9B 105.50(11) . . ?
C9 C9A C9B 135.51(13) . . ?
C4A C9B C9A 106.13(11) . . ?
C4A C9B C10 122.54(11) . . ?
C9A C9B C10 130.98(11) . . ?
C9B C10 C11 113.56(10) . . ?
C9B C10 C10A 105.27(10) . . ?
C11 C10 C10A 111.57(10) . . ?
C1 C10A C10 121.14(10) . . ?
C1 C10A C3A 104.31(10) . . ?
C10 C10A C3A 111.61(10) . . ?
O2 C11 O3 123.90(12) . . ?
O2 C11 C10 123.78(11) . . ?
O3 C11 C10 112.30(11) . . ?
C13 C12 C17 119.97(12) . . ?
C13 C12 N2 121.30(11) . . ?
C17 C12 N2 118.72(12) . . ?
C12 C13 C14 119.14(13) . . ?
C15 C14 C13 121.04(14) . . ?
C16 C15 C14 119.53(13) . . ?
C15 C16 C17 120.44(13) . . ?
C16 C17 C12 119.88(13) . . ?

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
C12 N2 C1 O1 -6.1(2) . . . . ?
C3 N2 C1 O1 -172.19(12) . . . . ?
C12 N2 C1 C10A 167.50(11) . . . . ?
C3 N2 C1 C10A 1.45(13) . . . . ?
C1 N2 C3 C3A -20.81(13) . . . . ?
C12 N2 C3 C3A 172.25(10) . . . . ?
N2 C3 C3A C4 151.97(10) . . . . ?
N2 C3 C3A C10A 30.53(12) . . . . ?
C3 C3A C4 C4A -161.25(11) . . . . ?
C10A C3A C4 C4A -43.94(13) . . . . ?
C5A O5 C4A C9B 1.03(14) . . . . ?
C5A O5 C4A C4 -176.44(11) . . . . ?
C3A C4 C4A C9B 10.28(18) . . . . ?
C3A C4 C4A O5 -172.73(10) . . . . ?
C4A O5 C5A C6 176.46(13) . . . . ?
C4A O5 C5A C9A -1.19(13) . . . . ?
O5 C5A C6 C7 -177.09(12) . . . . ?
C9A C5A C6 C7 0.3(2) . . . . ?
C5A C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C9A 0.7(2) . . . . ?
O5 C5A C9A C9 177.92(11) . . . . ?
C6 C5A C9A C9 0.2(2) . . . . ?
O5 C5A C9A C9B 0.92(14) . . . . ?
C6 C5A C9A C9B -176.76(12) . . . . ?
C8 C9 C9A C5A -0.68(19) . . . . ?
C8 C9 C9A C9B 175.19(13) . . . . ?
O5 C4A C9B C9A -0.48(14) . . . . ?
C4 C4A C9B C9A 176.67(12) . . . . ?
O5 C4A C9B C10 -174.37(11) . . . . ?
C4 C4A C9B C10 2.8(2) . . . . ?
C5A C9A C9B C4A -0.27(13) . . . . ?
C9 C9A C9B C4A -176.52(14) . . . . ?
C5A C9A C9B C10 172.90(12) . . . . ?
C9 C9A C9B C10 -3.3(2) . . . . ?
C4A C9B C10 C11 -104.10(14) . . . . ?
C9A C9B C10 C11 83.69(16) . . . . ?
C4A C9B C10 C10A 18.22(15) . . . . ?
C9A C9B C10 C10A -153.99(12) . . . . ?
O1 C1 C10A C10 -41.22(18) . . . . ?
N2 C1 C10A C10 145.28(11) . . . . ?
O1 C1 C10A C3A -167.97(12) . . . . ?
N2 C1 C10A C3A 18.53(13) . . . . ?
C9B C10 C10A C1 -176.31(10) . . . . ?
C11 C10 C10A C1 -52.71(14) . . . . ?
C9B C10 C10A C3A -52.94(12) . . . . ?
C11 C10 C10A C3A 70.66(13) . . . . ?
C3 C3A C10A C1 -30.27(12) . . . . ?
C4 C3A C10A C1 -156.35(10) . . . . ?
C3 C3A C10A C10 -162.74(10) . . . . ?
C4 C3A C10A C10 71.18(13) . . . . ?
C9B C10 C11 O2 136.90(13) . . . . ?
C10A C10 C11 O2 18.14(17) . . . . ?
C9B C10 C11 O3 -44.67(14) . . . . ?
C10A C10 C11 O3 -163.43(10) . . . . ?
C1 N2 C12 C13 33.30(18) . . . . ?
C3 N2 C12 C13 -161.64(11) . . . . ?
C1 N2 C12 C17 -147.90(12) . . . . ?
C3 N2 C12 C17 17.16(16) . . . . ?
C17 C12 C13 C14 0.42(19) . . . . ?
N2 C12 C13 C14 179.20(12) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C12 -0.36(19) . . . . ?
C13 C12 C17 C16 -0.05(18) . . . . ?
N2 C12 C17 C16 -178.86(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.90(2) 1.79(2) 2.6637(13) 161(2) 2_645 yes
C3 H3B O3 0.99 2.53 3.4052(16) 147.3 4_566 yes
C10 H10B O2 1.00 2.42 3.3711(15) 158.4 2_655 yes
C13 H13A O1 0.95 2.40 2.9147(16) 113.4 . yes

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.056


# start Validation Reply Form
_vrf_PLAT910_ZV2253              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 13 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_12a
_database_code_depnum_ccdc_archive 'CCDC 2513916'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-12-07 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   25.1111(6)
_cell_length_b                   8.92502(12)
_cell_length_c                   18.2650(5)
_cell_angle_alpha                90
_cell_angle_beta                 127.400(4)
_cell_angle_gamma                90
_cell_volume                     3251.93(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13718
_cell_measurement_theta_min      4.437
_cell_measurement_theta_max      78.948

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.787
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.118a (Rigaku Oxford Diffraction, 2025).
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24152
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.433
_diffrn_reflns_theta_max         79.768
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3513
_reflns_number_gt                3223
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+4.8386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3513
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.50326(9) 0.7795(2) 0.41996(13) 0.0315(4) Uani 1 1 d . . . . .
H1A H 0.471681 0.736525 0.429755 0.038 Uiso 1 1 calc R U . . .
H1B H 0.478494 0.848756 0.366715 0.038 Uiso 1 1 calc R U . . .
C2 C 0.56183(8) 0.86088(18) 0.50753(11) 0.0257(3) Uani 1 1 d . . . . .
H2A H 0.572147 0.956889 0.491449 0.031 Uiso 1 1 calc R U . . .
H2B H 0.550802 0.881239 0.550225 0.031 Uiso 1 1 calc R U . . .
C3 C 0.62127(8) 0.75168(18) 0.55117(11) 0.0231(3) Uani 1 1 d . . . . .
H3A H 0.664544 0.805402 0.591191 0.028 Uiso 1 1 calc R U . . .
H3B H 0.619112 0.673885 0.587937 0.028 Uiso 1 1 calc R U . . .
C3A C 0.61237(7) 0.68258(16) 0.46727(10) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.63417(8) 0.79435(17) 0.42557(11) 0.0231(3) Uani 1 1 d . . . . .
H4A H 0.595988 0.857703 0.378189 0.028 Uiso 1 1 calc R U . . .
H4B H 0.670698 0.859885 0.473987 0.028 Uiso 1 1 calc R U . . .
N5 N 0.65749(6) 0.70009(14) 0.38431(9) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.67066(7) 0.55802(17) 0.41714(10) 0.0188(3) Uani 1 1 d . . . . .
O6 O 0.69293(6) 0.45702(12) 0.39687(8) 0.0244(3) Uani 1 1 d . . . . .
C6A C 0.65412(7) 0.54217(16) 0.48440(10) 0.0177(3) Uani 1 1 d . . . . .
H6A H 0.696845 0.546715 0.548627 0.021 Uiso 1 1 calc R U . . .
C7 C 0.61954(8) 0.39161(17) 0.47153(10) 0.0205(3) Uani 1 1 d . . . . .
H7 H 0.610745 0.386092 0.518025 0.025 Uiso 1 1 calc R U . . .
C7A C 0.55142(9) 0.38856(19) 0.37482(12) 0.0277(4) Uani 1 1 d . . . . .
H7A H 0.558995 0.392491 0.327061 0.033 Uiso 1 1 calc R U . . .
C8 C 0.50120(9) 0.2665(2) 0.35025(12) 0.0290(4) Uani 1 1 d . . . . .
H8 H 0.509949 0.161927 0.358220 0.035 Uiso 1 1 calc R U . . .
C9 C 0.44322(9) 0.3310(2) 0.31587(12) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.403330 0.275675 0.291300 0.038 Uiso 1 1 calc R U . . .
O10 O 0.44518(6) 0.48625(15) 0.31848(9) 0.0331(3) Uani 1 1 d . . . . .
C10A C 0.51236(8) 0.52357(18) 0.36560(10) 0.0221(3) Uani 1 1 d . . . . .
C10B C 0.53732(8) 0.65710(19) 0.40471(11) 0.0258(3) Uani 1 1 d . . . . .
C11 C 0.67027(7) 0.76285(17) 0.32458(10) 0.0191(3) Uani 1 1 d . . . . .
C12 C 0.66806(8) 0.91859(17) 0.31465(11) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.658997 0.980660 0.348157 0.027 Uiso 1 1 calc R U . . .
C13 C 0.67921(8) 0.98226(18) 0.25547(12) 0.0258(3) Uani 1 1 d . . . . .
H13 H 0.677500 1.088064 0.248657 0.031 Uiso 1 1 calc R U . . .
C14 C 0.69275(8) 0.89361(19) 0.20646(11) 0.0256(3) Uani 1 1 d . . . . .
H14 H 0.700183 0.937828 0.166054 0.031 Uiso 1 1 calc R U . . .
C15 C 0.69534(8) 0.73912(19) 0.21709(11) 0.0233(3) Uani 1 1 d . . . . .
H15 H 0.705049 0.677761 0.184048 0.028 Uiso 1 1 calc R U . . .
C16 C 0.68395(8) 0.67279(17) 0.27528(10) 0.0209(3) Uani 1 1 d . . . . .
H16 H 0.685461 0.566885 0.281483 0.025 Uiso 1 1 calc R U . . .
C17 C 0.66229(8) 0.25801(17) 0.48626(11) 0.0214(3) Uani 1 1 d . . . . .
O17 O 0.64136(6) 0.14943(13) 0.43665(9) 0.0318(3) Uani 1 1 d . . . . .
O18 O 0.72510(6) 0.27105(13) 0.56248(8) 0.0230(3) Uani 1 1 d . . . . .
H18 H 0.7486(11) 0.190(3) 0.5698(15) 0.034 Uiso 1 1 d . 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
C1 C10B 1.514(2) . ?
C1 C2 1.547(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.539(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C3A 1.537(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C10B 1.514(2) . ?
C3A C6A 1.5392(19) . ?
C3A C4 1.543(2) . ?
C4 N5 1.4680(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N5 C6 1.3549(19) . ?
N5 C11 1.4255(18) . ?
C6 O6 1.2304(18) . ?
C6 C6A 1.5235(19) . ?
C6A C7 1.539(2) . ?
C6A H6A 1.0000 . ?
C7 C17 1.515(2) . ?
C7 C7A 1.542(2) . ?
C7 H7 1.0000 . ?
C7A C10A 1.497(2) . ?
C7A C8 1.513(2) . ?
C7A H7A 1.0000 . ?
C8 C9 1.317(3) . ?
C8 H8 0.9500 . ?
C9 O10 1.386(2) . ?
C9 H9 0.9500 . ?
O10 C10A 1.3906(19) . ?
C10A C10B 1.334(2) . ?
C11 C16 1.397(2) . ?
C11 C12 1.399(2) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.207(2) . ?
C17 O18 1.331(2) . ?
O18 H18 0.89(2) . ?

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
C10B C1 C2 103.92(13) . . ?
C10B C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
C10B C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C3 C2 C1 104.61(13) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C3A C3 C2 103.28(12) . . ?
C3A C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C3A C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C10B C3A C3 99.98(12) . . ?
C10B C3A C6A 114.39(12) . . ?
C3 C3A C6A 117.09(12) . . ?
C10B C3A C4 112.13(13) . . ?
C3 C3A C4 110.63(12) . . ?
C6A C3A C4 102.98(11) . . ?
N5 C4 C3A 104.76(12) . . ?
N5 C4 H4A 110.8 . . ?
C3A C4 H4A 110.8 . . ?
N5 C4 H4B 110.8 . . ?
C3A C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C6 N5 C11 126.78(12) . . ?
C6 N5 C4 112.04(12) . . ?
C11 N5 C4 120.87(12) . . ?
O6 C6 N5 125.85(14) . . ?
O6 C6 C6A 124.82(13) . . ?
N5 C6 C6A 109.33(12) . . ?
C6 C6A C7 111.28(12) . . ?
C6 C6A C3A 104.25(11) . . ?
C7 C6A C3A 115.37(12) . . ?
C6 C6A H6A 108.6 . . ?
C7 C6A H6A 108.6 . . ?
C3A C6A H6A 108.6 . . ?
C17 C7 C6A 112.76(12) . . ?
C17 C7 C7A 111.28(13) . . ?
C6A C7 C7A 108.72(12) . . ?
C17 C7 H7 108.0 . . ?
C6A C7 H7 108.0 . . ?
C7A C7 H7 108.0 . . ?
C10A C7A C8 100.06(14) . . ?
C10A C7A C7 108.05(13) . . ?
C8 C7A C7 119.82(14) . . ?
C10A C7A H7A 109.4 . . ?
C8 C7A H7A 109.4 . . ?
C7 C7A H7A 109.4 . . ?
C9 C8 C7A 107.93(16) . . ?
C9 C8 H8 126.0 . . ?
C7A C8 H8 126.0 . . ?
C8 C9 O10 114.48(15) . . ?
C8 C9 H9 122.8 . . ?
O10 C9 H9 122.8 . . ?
C9 O10 C10A 105.37(13) . . ?
C10B C10A O10 122.98(15) . . ?
C10B C10A C7A 126.59(14) . . ?
O10 C10A C7A 110.02(13) . . ?
C10A C10B C1 127.51(15) . . ?
C10A C10B C3A 120.19(14) . . ?
C1 C10B C3A 109.64(13) . . ?
C16 C11 C12 119.62(14) . . ?
C16 C11 N5 121.68(13) . . ?
C12 C11 N5 118.70(13) . . ?
C13 C12 C11 119.72(14) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.90(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.12(15) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 121.08(15) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 119.57(14) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
O17 C17 O18 123.66(15) . . ?
O17 C17 C7 124.05(15) . . ?
O18 C17 C7 112.24(13) . . ?
C17 O18 H18 110.0(14) . . ?

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
C10B C1 C2 C3 -16.40(18) . . . . ?
C1 C2 C3 C3A 37.36(16) . . . . ?
C2 C3 C3A C10B -42.51(15) . . . . ?
C2 C3 C3A C6A -166.63(13) . . . . ?
C2 C3 C3A C4 75.85(15) . . . . ?
C10B C3A C4 N5 -98.50(14) . . . . ?
C3 C3A C4 N5 150.83(12) . . . . ?
C6A C3A C4 N5 24.96(15) . . . . ?
C3A C4 N5 C6 -17.55(17) . . . . ?
C3A C4 N5 C11 168.46(13) . . . . ?
C11 N5 C6 O6 -3.9(3) . . . . ?
C4 N5 C6 O6 -177.44(15) . . . . ?
C11 N5 C6 C6A 175.62(13) . . . . ?
C4 N5 C6 C6A 2.07(17) . . . . ?
O6 C6 C6A C7 -41.2(2) . . . . ?
N5 C6 C6A C7 139.27(13) . . . . ?
O6 C6 C6A C3A -166.20(14) . . . . ?
N5 C6 C6A C3A 14.29(16) . . . . ?
C10B C3A C6A C6 98.32(14) . . . . ?
C3 C3A C6A C6 -145.22(13) . . . . ?
C4 C3A C6A C6 -23.62(14) . . . . ?
C10B C3A C6A C7 -24.01(18) . . . . ?
C3 C3A C6A C7 92.45(16) . . . . ?
C4 C3A C6A C7 -145.95(13) . . . . ?
C6 C6A C7 C17 59.59(16) . . . . ?
C3A C6A C7 C17 178.08(12) . . . . ?
C6 C6A C7 C7A -64.31(16) . . . . ?
C3A C6A C7 C7A 54.18(16) . . . . ?
C17 C7 C7A C10A -179.92(13) . . . . ?
C6A C7 C7A C10A -55.14(16) . . . . ?
C17 C7 C7A C8 66.59(19) . . . . ?
C6A C7 C7A C8 -168.63(14) . . . . ?
C10A C7A C8 C9 11.50(18) . . . . ?
C7 C7A C8 C9 129.18(17) . . . . ?
C7A C8 C9 O10 -4.9(2) . . . . ?
C8 C9 O10 C10A -4.8(2) . . . . ?
C9 O10 C10A C10B -160.47(16) . . . . ?
C9 O10 C10A C7A 12.59(18) . . . . ?
C8 C7A C10A C10B 158.07(17) . . . . ?
C7 C7A C10A C10B 32.0(2) . . . . ?
C8 C7A C10A O10 -14.68(17) . . . . ?
C7 C7A C10A O10 -140.77(13) . . . . ?
O10 C10A C10B C1 11.0(3) . . . . ?
C7A C10A C10B C1 -160.89(17) . . . . ?
O10 C10A C10B C3A 170.52(14) . . . . ?
C7A C10A C10B C3A -1.4(3) . . . . ?
C2 C1 C10B C10A 150.40(17) . . . . ?
C2 C1 C10B C3A -10.88(19) . . . . ?
C3 C3A C10B C10A -129.52(16) . . . . ?
C6A C3A C10B C10A -3.5(2) . . . . ?
C4 C3A C10B C10A 113.24(17) . . . . ?
C3 C3A C10B C1 33.35(17) . . . . ?
C6A C3A C10B C1 159.32(14) . . . . ?
C4 C3A C10B C1 -83.90(16) . . . . ?
C6 N5 C11 C16 15.5(2) . . . . ?
C4 N5 C11 C16 -171.50(14) . . . . ?
C6 N5 C11 C12 -165.37(15) . . . . ?
C4 N5 C11 C12 7.7(2) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
N5 C11 C12 C13 -178.88(14) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C11 -0.6(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
N5 C11 C16 C15 179.28(14) . . . . ?
C6A C7 C17 O17 -135.72(16) . . . . ?
C7A C7 C17 O17 -13.2(2) . . . . ?
C6A C7 C17 O18 46.93(16) . . . . ?
C7A C7 C17 O18 169.41(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12 O17 0.95 2.44 3.387(2) 177 1_565 yes
C16 H16 O6 0.95 2.23 2.8431(19) 122 . yes
O18 H18 O6 0.89(2) 1.78(2) 2.6599(15) 170(2) 7_656 yes

_refine_diff_density_max         0.619
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_23g
_database_code_depnum_ccdc_archive 'CCDC 2513919'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2025-12-07 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 F3 N O4, C2 H6 O S'
_chemical_formula_sum            'C24 H22 F3 N O5 S'
_chemical_formula_weight         493.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.69436(16)
_cell_length_b                   7.4987(2)
_cell_length_c                   23.1930(6)
_cell_angle_alpha                80.904(2)
_cell_angle_beta                 85.135(2)
_cell_angle_gamma                72.729(2)
_cell_volume                     1096.90(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15218
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      78.97

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.883
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26336
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.863
_diffrn_reflns_theta_max         79.938
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4689
_reflns_number_gt                4317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0774P)²+1.3324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4689
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.1483(2) 0.5780(2) -0.03438(6) 0.0350(3) Uani 1 1 d . . . . .
F2 F 0.2167(3) 0.8423(3) -0.04345(7) 0.0479(4) Uani 1 1 d . . . . .
F3 F -0.0950(3) 0.8263(3) -0.01694(7) 0.0476(5) Uani 1 1 d . . . . .
O1 O 0.6887(2) 0.5547(2) 0.22079(7) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.7322(3) 0.1513(2) 0.28772(8) 0.0321(4) Uani 1 1 d . . . . .
O3 O 1.0106(3) 0.1580(2) 0.33355(8) 0.0288(4) Uani 1 1 d . . . . .
H3 H 1.083(7) 0.068(6) 0.3081(19) 0.068(12) Uiso 1 1 d . . . . .
C1 C 0.1761(3) 0.5610(3) 0.27584(9) 0.0193(4) Uani 1 1 d . . . . .
H1A H 0.0772 0.4958 0.2662 0.023 Uiso 1 1 calc R U . . .
H1B H 0.0967 0.6887 0.2846 0.023 Uiso 1 1 calc R U . . .
N2 N 0.3356(3) 0.5695(2) 0.22825(7) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.5279(3) 0.5476(3) 0.24969(9) 0.0199(4) Uani 1 1 d . . . . .
C3A C 0.5041(3) 0.5188(3) 0.31539(9) 0.0182(4) Uani 1 1 d . . . . .
H3A H 0.4665 0.6459 0.3285 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6944(3) 0.3942(3) 0.34890(9) 0.0193(4) Uani 1 1 d . . . . .
H4 H 0.7922 0.4703 0.3517 0.023 Uiso 1 1 calc R U . . .
C4A C 0.6105(3) 0.3399(3) 0.40887(9) 0.0193(4) Uani 1 1 d . . . . .
O5 O 0.7500(2) 0.2447(2) 0.45183(6) 0.0215(3) Uani 1 1 d . . . . .
C5A C 0.6252(3) 0.2125(3) 0.50076(9) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.6964(4) 0.1140(3) 0.55426(10) 0.0241(4) Uani 1 1 d . . . . .
H6 H 0.8415 0.0619 0.5612 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5431(4) 0.0958(3) 0.59715(9) 0.0256(5) Uani 1 1 d . . . . .
H7 H 0.5842 0.0300 0.6347 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3296(4) 0.1720(3) 0.58653(10) 0.0253(5) Uani 1 1 d . . . . .
H8 H 0.2292 0.1570 0.6170 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2619(4) 0.2688(3) 0.53247(9) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.1168 0.3195 0.5254 0.027 Uiso 1 1 calc R U . . .
C9A C 0.4135(3) 0.2897(3) 0.48860(9) 0.0198(4) Uani 1 1 d . . . . .
C9B C 0.4084(3) 0.3710(3) 0.42789(9) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.2256(3) 0.4615(3) 0.38930(9) 0.0211(4) Uani 1 1 d . . . . .
H10A H 0.1627 0.5951 0.3949 0.025 Uiso 1 1 calc R U . . .
H10B H 0.1170 0.3948 0.3986 0.025 Uiso 1 1 calc R U . . .
C10A C 0.3107(3) 0.4475(3) 0.32663(9) 0.0185(4) Uani 1 1 d . . . . .
H10C H 0.3535 0.3116 0.3210 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2832(3) 0.6153(3) 0.16923(9) 0.0190(4) Uani 1 1 d . . . . .
C12 C 0.0717(3) 0.6753(3) 0.15567(9) 0.0214(4) Uani 1 1 d . . . . .
H12 H -0.0332 0.6886 0.1863 0.026 Uiso 1 1 calc R U . . .
C13 C 0.0138(4) 0.7157(3) 0.09783(10) 0.0243(4) Uani 1 1 d . . . . .
H13 H -0.1301 0.7547 0.0891 0.029 Uiso 1 1 calc R U . . .
C14 C 0.1654(4) 0.6991(3) 0.05291(10) 0.0254(5) Uani 1 1 d . . . . .
C15 C 0.3761(4) 0.6414(3) 0.06603(10) 0.0272(5) Uani 1 1 d . . . . .
H15 H 0.4802 0.6317 0.0352 0.033 Uiso 1 1 calc R U . . .
C16 C 0.4357(4) 0.5980(3) 0.12363(10) 0.0243(4) Uani 1 1 d . . . . .
H16 H 0.5800 0.5564 0.1321 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1080(4) 0.7365(3) -0.00957(10) 0.0307(5) Uani 1 1 d . . . . .
C18 C 0.8114(3) 0.2214(3) 0.31988(9) 0.0217(4) Uani 1 1 d . . . . .
S1 S 0.29864(9) 0.13360(7) 0.21395(2) 0.02799(16) Uani 1 1 d . . . . .
O4 O 0.2590(3) -0.0279(2) 0.25654(8) 0.0305(4) Uani 1 1 d . . . . .
C19 C 0.1295(5) 0.1683(4) 0.15517(13) 0.0443(7) Uani 1 1 d . . . . .
H19A H 0.1513 0.0485 0.1402 0.066 Uiso 1 1 calc R U . . .
H19B H 0.1607 0.2614 0.1238 0.066 Uiso 1 1 calc R U . . .
H19C H -0.0165 0.2141 0.1692 0.066 Uiso 1 1 calc R U . . .
C20 C 0.5437(5) 0.0375(4) 0.17792(13) 0.0399(6) Uani 1 1 d . . . . .
H20A H 0.6555 0.0046 0.2058 0.060 Uiso 1 1 calc R U . . .
H20B H 0.5693 0.1309 0.1458 0.060 Uiso 1 1 calc R U . . .
H20C H 0.5412 -0.0759 0.1624 0.060 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
F1 C17 1.348(3) . ?
F2 C17 1.351(3) . ?
F3 C17 1.337(3) . ?
O1 C3 1.229(3) . ?
O2 C18 1.213(3) . ?
O3 C18 1.324(3) . ?
O3 H3 0.96(5) . ?
C1 N2 1.477(2) . ?
C1 C10A 1.527(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C3 1.374(3) . ?
N2 C11 1.406(3) . ?
C3 C3A 1.507(3) . ?
C3A C4 1.527(3) . ?
C3A C10A 1.530(3) . ?
C3A H3A 1.0000 . ?
C4 C4A 1.497(3) . ?
C4 C18 1.526(3) . ?
C4 H4 1.0000 . ?
C4A C9B 1.350(3) . ?
C4A O5 1.383(2) . ?
O5 C5A 1.384(3) . ?
C5A C6 1.383(3) . ?
C5A C9A 1.397(3) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C9A 1.400(3) . ?
C9 H9 0.9500 . ?
C9A C9B 1.442(3) . ?
C9B C10 1.503(3) . ?
C10 C10A 1.523(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10A H10C 1.0000 . ?
C11 C12 1.400(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 C17 1.493(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
S1 O4 1.5103(17) . ?
S1 C20 1.779(3) . ?
S1 C19 1.784(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
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
C18 O3 H3 108(3) . . ?
N2 C1 C10A 101.83(15) . . ?
N2 C1 H1A 111.4 . . ?
C10A C1 H1A 111.4 . . ?
N2 C1 H1B 111.4 . . ?
C10A C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
C3 N2 C11 126.23(18) . . ?
C3 N2 C1 111.57(16) . . ?
C11 N2 C1 121.85(17) . . ?
O1 C3 N2 126.51(19) . . ?
O1 C3 C3A 126.15(19) . . ?
N2 C3 C3A 107.31(17) . . ?
C3 C3A C4 117.11(17) . . ?
C3 C3A C10A 103.03(16) . . ?
C4 C3A C10A 114.06(16) . . ?
C3 C3A H3A 107.4 . . ?
C4 C3A H3A 107.4 . . ?
C10A C3A H3A 107.4 . . ?
C4A C4 C18 111.66(17) . . ?
C4A C4 C3A 105.37(16) . . ?
C18 C4 C3A 112.63(17) . . ?
C4A C4 H4 109.0 . . ?
C18 C4 H4 109.0 . . ?
C3A C4 H4 109.0 . . ?
C9B C4A O5 113.07(18) . . ?
C9B C4A C4 128.03(19) . . ?
O5 C4A C4 118.90(18) . . ?
C4A O5 C5A 104.72(16) . . ?
C6 C5A O5 125.6(2) . . ?
C6 C5A C9A 123.8(2) . . ?
O5 C5A C9A 110.58(18) . . ?
C5A C6 C7 116.0(2) . . ?
C5A C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
C6 C7 C8 121.8(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C9A 118.0(2) . . ?
C8 C9 H9 121.0 . . ?
C9A C9 H9 121.0 . . ?
C5A C9A C9 119.21(19) . . ?
C5A C9A C9B 105.85(18) . . ?
C9 C9A C9B 134.9(2) . . ?
C4A C9B C9A 105.76(18) . . ?
C4A C9B C10 123.94(19) . . ?
C9A C9B C10 130.17(19) . . ?
C9B C10 C10A 106.53(17) . . ?
C9B C10 H10A 110.4 . . ?
C10A C10 H10A 110.4 . . ?
C9B C10 H10B 110.4 . . ?
C10A C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C10 C10A C1 119.91(17) . . ?
C10 C10A C3A 110.61(17) . . ?
C1 C10A C3A 101.46(16) . . ?
C10 C10A H10C 108.1 . . ?
C1 C10A H10C 108.1 . . ?
C3A C10A H10C 108.1 . . ?
C12 C11 C16 118.99(19) . . ?
C12 C11 N2 118.86(19) . . ?
C16 C11 N2 122.13(19) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 C17 121.3(2) . . ?
C15 C14 C17 119.0(2) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
F3 C17 F1 106.2(2) . . ?
F3 C17 F2 106.7(2) . . ?
F1 C17 F2 104.84(19) . . ?
F3 C17 C14 113.0(2) . . ?
F1 C17 C14 113.06(19) . . ?
F2 C17 C14 112.5(2) . . ?
O2 C18 O3 123.9(2) . . ?
O2 C18 C4 124.2(2) . . ?
O3 C18 C4 111.92(19) . . ?
O4 S1 C20 105.48(12) . . ?
O4 S1 C19 105.89(13) . . ?
C20 S1 C19 99.52(15) . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S1 C20 H20C 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
C10A C1 N2 C3 -24.1(2) . . . . ?
C10A C1 N2 C11 162.26(17) . . . . ?
C11 N2 C3 O1 -4.1(3) . . . . ?
C1 N2 C3 O1 -177.3(2) . . . . ?
C11 N2 C3 C3A 174.35(17) . . . . ?
C1 N2 C3 C3A 1.1(2) . . . . ?
O1 C3 C3A C4 -33.0(3) . . . . ?
N2 C3 C3A C4 148.55(18) . . . . ?
O1 C3 C3A C10A -159.1(2) . . . . ?
N2 C3 C3A C10A 22.5(2) . . . . ?
C3 C3A C4 C4A -162.25(17) . . . . ?
C10A C3A C4 C4A -41.9(2) . . . . ?
C3 C3A C4 C18 -40.3(2) . . . . ?
C10A C3A C4 C18 80.1(2) . . . . ?
C18 C4 C4A C9B -114.5(2) . . . . ?
C3A C4 C4A C9B 8.1(3) . . . . ?
C18 C4 C4A O5 65.1(2) . . . . ?
C3A C4 C4A O5 -172.27(17) . . . . ?
C9B C4A O5 C5A 0.8(2) . . . . ?
C4 C4A O5 C5A -178.86(18) . . . . ?
C4A O5 C5A C6 177.2(2) . . . . ?
C4A O5 C5A C9A -1.3(2) . . . . ?
O5 C5A C6 C7 -178.90(19) . . . . ?
C9A C5A C6 C7 -0.6(3) . . . . ?
C5A C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C9A -0.5(3) . . . . ?
C6 C5A C9A C9 0.3(3) . . . . ?
O5 C5A C9A C9 178.85(18) . . . . ?
C6 C5A C9A C9B -177.3(2) . . . . ?
O5 C5A C9A C9B 1.2(2) . . . . ?
C8 C9 C9A C5A 0.2(3) . . . . ?
C8 C9 C9A C9B 177.0(2) . . . . ?
O5 C4A C9B C9A 0.0(2) . . . . ?
C4 C4A C9B C9A 179.6(2) . . . . ?
O5 C4A C9B C10 -176.32(18) . . . . ?
C4 C4A C9B C10 3.3(4) . . . . ?
C5A C9A C9B C4A -0.7(2) . . . . ?
C9 C9A C9B C4A -177.8(2) . . . . ?
C5A C9A C9B C10 175.2(2) . . . . ?
C9 C9A C9B C10 -1.8(4) . . . . ?
C4A C9B C10 C10A 18.1(3) . . . . ?
C9A C9B C10 C10A -157.2(2) . . . . ?
C9B C10 C10A C1 -167.41(18) . . . . ?
C9B C10 C10A C3A -50.0(2) . . . . ?
N2 C1 C10A C10 158.21(18) . . . . ?
N2 C1 C10A C3A 36.15(19) . . . . ?
C3 C3A C10A C10 -164.33(16) . . . . ?
C4 C3A C10A C10 67.7(2) . . . . ?
C3 C3A C10A C1 -36.04(18) . . . . ?
C4 C3A C10A C1 -164.03(16) . . . . ?
C3 N2 C11 C12 -165.22(19) . . . . ?
C1 N2 C11 C12 7.4(3) . . . . ?
C3 N2 C11 C16 16.6(3) . . . . ?
C1 N2 C11 C16 -170.80(19) . . . . ?
C16 C11 C12 C13 0.5(3) . . . . ?
N2 C11 C12 C13 -177.78(19) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C17 178.3(2) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C17 C14 C15 C16 -177.4(2) . . . . ?
C14 C15 C16 C11 -1.2(3) . . . . ?
C12 C11 C16 C15 0.5(3) . . . . ?
N2 C11 C16 C15 178.7(2) . . . . ?
C13 C14 C17 F3 14.5(3) . . . . ?
C15 C14 C17 F3 -167.3(2) . . . . ?
C13 C14 C17 F1 -106.1(3) . . . . ?
C15 C14 C17 F1 72.1(3) . . . . ?
C13 C14 C17 F2 135.4(2) . . . . ?
C15 C14 C17 F2 -46.4(3) . . . . ?
C4A C4 C18 O2 93.8(3) . . . . ?
C3A C4 C18 O2 -24.6(3) . . . . ?
C4A C4 C18 O3 -86.8(2) . . . . ?
C3A C4 C18 O3 154.82(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.96(5) 1.69(5) 2.609(2) 158(4) 1_655

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_zv2108
_database_code_depnum_ccdc_archive 'CCDC 2495037'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2025-10-13 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8.50 D3 F3 N0.50 O3 S0.50'
_chemical_formula_weight         298.77

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9019(6)
_cell_length_b                   13.4092(9)
_cell_length_c                   21.1363(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2523.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      29.23

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48308
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.599
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7330
_reflns_number_gt                6555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.2371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(7)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         7330
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.72758(6) 0.76623(5) 0.44887(2) 0.02422(12) Uani 1 1 d . . . . .
F1 F 0.07630(14) 0.84627(8) 0.32403(6) 0.0191(2) Uani 1 1 d . . . . .
F2 F -0.03834(12) 0.72447(9) 0.27872(5) 0.0198(2) Uani 1 1 d . . . . .
F3 F 0.03765(12) 0.71017(9) 0.37569(5) 0.0173(2) Uani 1 1 d . . . . .
F4 F 0.21092(15) 0.07346(9) 0.34242(6) 0.0268(3) Uani 1 1 d . . . . .
F5 F 0.28176(16) 0.04270(10) 0.43810(6) 0.0291(3) Uani 1 1 d . . . . .
F6 F 0.43150(14) 0.01306(9) 0.36006(6) 0.0240(3) Uani 1 1 d . . . . .
O1 O 0.30802(16) 0.55542(10) 0.40320(6) 0.0182(3) Uani 1 1 d . . . . .
O2 O 0.33460(15) 0.78753(11) 0.38403(6) 0.0191(3) Uani 1 1 d . . . . .
O3 O 0.48319(15) 0.70719(11) 0.31481(7) 0.0184(3) Uani 1 1 d . . . . .
H3A H 0.566(5) 0.732(3) 0.3389(17) 0.069(11) Uiso 1 1 d . . . . .
O4 O 0.57174(17) 0.12124(10) 0.45881(7) 0.0185(3) Uani 1 1 d . . . . .
O5 O 0.09160(16) 0.72399(11) 0.13352(7) 0.0201(3) Uani 1 1 d . . . . .
O6 O 0.70922(16) 0.75840(13) 0.37759(7) 0.0270(3) Uani 1 1 d . . . . .
N2 N 0.31397(18) 0.43588(12) 0.32421(7) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.2836(2) 0.52813(14) 0.34907(8) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.2610(2) 0.42518(15) 0.25831(9) 0.0180(4) Uani 1 1 d . . . . .
H3B H 0.159(3) 0.3993(18) 0.2588(11) 0.018(6) Uiso 1 1 d . . . . .
H3C H 0.332(3) 0.379(2) 0.2353(12) 0.030(7) Uiso 1 1 d . . . . .
C3A C 0.2645(2) 0.53348(14) 0.23637(9) 0.0145(3) Uani 1 1 d . . . . .
H3AA H 0.371(3) 0.5509(18) 0.2327(11) 0.015(6) Uiso 1 1 d . . . . .
C4 C 0.1726(2) 0.56763(15) 0.18079(9) 0.0180(4) Uani 1 1 d . . . . .
H4A H 0.121(3) 0.524(2) 0.1536(12) 0.025(7) Uiso 1 1 d . . . . .
C4A C 0.1681(2) 0.66682(15) 0.17796(9) 0.0161(4) Uani 1 1 d . . . . .
C5A C 0.1244(2) 0.82312(15) 0.14678(9) 0.0172(4) Uani 1 1 d . . . . .
C6 C 0.0803(2) 0.90179(17) 0.10895(11) 0.0236(4) Uani 1 1 d . . . . .
H6A H 0.024(3) 0.891(2) 0.0724(14) 0.033(8) Uiso 1 1 d . . . . .
C7 C 0.1291(2) 0.99642(17) 0.12707(11) 0.0240(4) Uani 1 1 d . . . . .
H7A H 0.105(3) 1.057(2) 0.1017(12) 0.024(6) Uiso 1 1 d . . . . .
C8 C 0.2166(3) 1.01081(16) 0.18099(10) 0.0234(4) Uani 1 1 d . . . . .
H8A H 0.249(3) 1.076(2) 0.1901(12) 0.028(7) Uiso 1 1 d . . . . .
C9 C 0.2610(2) 0.92940(16) 0.21756(10) 0.0205(4) Uani 1 1 d . . . . .
H9A H 0.321(3) 0.942(2) 0.2551(14) 0.037(8) Uiso 1 1 d . . . . .
C9A C 0.2128(2) 0.83508(14) 0.20024(9) 0.0161(4) Uani 1 1 d . . . . .
C9B C 0.2540(2) 0.73208(15) 0.22389(8) 0.0153(3) Uani 1 1 d . . . . .
H9BA H 0.369(3) 0.721(2) 0.2163(13) 0.029(7) Uiso 1 1 d . . . . .
C10A C 0.2079(2) 0.58679(13) 0.29638(8) 0.0128(3) Uani 1 1 d . . . . .
H10A H 0.104(2) 0.5724(16) 0.2970(10) 0.008(5) Uiso 1 1 d . . . . .
C10 C 0.2225(2) 0.70235(13) 0.29465(8) 0.0124(3) Uani 1 1 d . . . . .
C11 C 0.3522(2) 0.73831(14) 0.33708(8) 0.0138(3) Uani 1 1 d . . . . .
C12 C 0.0753(2) 0.74706(14) 0.31870(9) 0.0148(3) Uani 1 1 d . . . . .
C13 C 0.3783(2) 0.35652(14) 0.35959(9) 0.0138(3) Uani 1 1 d . . . . .
C14 C 0.3248(2) 0.25963(14) 0.35308(9) 0.0148(3) Uani 1 1 d . . . . .
H14A H 0.243(3) 0.2414(19) 0.3259(12) 0.027(7) Uiso 1 1 d . . . . .
C15 C 0.3903(2) 0.18204(14) 0.38741(9) 0.0145(3) Uani 1 1 d . . . . .
C16 C 0.5118(2) 0.20132(14) 0.42819(9) 0.0148(4) Uani 1 1 d . . . . .
C17 C 0.5627(2) 0.29857(15) 0.43508(9) 0.0160(4) Uani 1 1 d . . . . .
H17A H 0.643(3) 0.3138(18) 0.4608(11) 0.014(6) Uiso 1 1 d . . . . .
C18 C 0.4967(2) 0.37544(15) 0.40105(9) 0.0157(4) Uani 1 1 d . . . . .
H18A H 0.528(3) 0.4408(18) 0.4068(10) 0.011(5) Uiso 1 1 d . . . . .
C19 C 0.3293(2) 0.07821(15) 0.38177(10) 0.0181(4) Uani 1 1 d . . . . .
C20 C 0.7107(3) 0.13699(17) 0.49222(10) 0.0226(4) Uani 1 1 d . . . . .
H20A H 0.740(3) 0.076(2) 0.5113(12) 0.027(7) Uiso 1 1 d . . . . .
H20B H 0.796(3) 0.160(2) 0.4635(13) 0.032(7) Uiso 1 1 d . . . . .
H20C H 0.696(3) 0.182(2) 0.5235(12) 0.022(6) Uiso 1 1 d . . . . .
C21 C 0.6221(3) 0.66578(19) 0.48211(12) 0.0271(5) Uani 1 1 d . . . . .
D21A D 0.679(4) 0.604(2) 0.4729(13) 0.037(8) Uiso 1 1 d . . . . .
D21B D 0.628(3) 0.673(2) 0.5265(14) 0.032(7) Uiso 1 1 d . . . . .
D21C D 0.522(4) 0.670(2) 0.4678(13) 0.032(7) Uiso 1 1 d . . . . .
C22 C 0.6105(3) 0.86686(18) 0.47373(12) 0.0270(5) Uani 1 1 d . . . . .
D22A D 0.642(4) 0.925(3) 0.4505(17) 0.052(9) Uiso 1 1 d . . . . .
D22B D 0.511(4) 0.852(2) 0.4630(13) 0.034(8) Uiso 1 1 d . . . . .
D22C D 0.625(3) 0.875(2) 0.5204(14) 0.034(7) 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 O6 1.5192(15) . ?
S1 C22 1.784(3) . ?
S1 C21 1.786(3) . ?
F1 C12 1.335(2) . ?
F2 C12 1.353(2) . ?
F3 C12 1.345(2) . ?
F4 C19 1.344(2) . ?
F5 C19 1.350(2) . ?
F6 C19 1.342(2) . ?
O1 C1 1.221(2) . ?
O2 C11 1.202(2) . ?
O3 C11 1.325(2) . ?
O3 H3A 0.96(4) . ?
O4 C16 1.363(2) . ?
O4 C20 1.440(2) . ?
O5 C5A 1.389(3) . ?
O5 C4A 1.390(2) . ?
N2 C1 1.371(2) . ?
N2 C13 1.421(2) . ?
N2 C3 1.478(2) . ?
C1 C10A 1.521(3) . ?
C3 C3A 1.525(3) . ?
C3 H3B 0.97(3) . ?
C3 H3C 1.01(3) . ?
C3A C4 1.503(3) . ?
C3A C10A 1.541(2) . ?
C3A H3AA 0.98(2) . ?
C4 C4A 1.332(3) . ?
C4 H4A 0.94(3) . ?
C4A C9B 1.514(3) . ?
C5A C6 1.381(3) . ?
C5A C9A 1.386(3) . ?
C6 C7 1.395(3) . ?
C6 H6A 0.93(3) . ?
C7 C8 1.394(3) . ?
C7 H7A 1.00(3) . ?
C8 C9 1.395(3) . ?
C8 H8A 0.94(3) . ?
C9 C9A 1.385(3) . ?
C9 H9A 0.97(3) . ?
C9A C9B 1.514(3) . ?
C9B C10 1.573(2) . ?
C9B H9BA 1.05(3) . ?
C10A C10 1.555(3) . ?
C10A H10A 0.95(2) . ?
C10 C12 1.527(3) . ?
C10 C11 1.540(3) . ?
C13 C14 1.391(3) . ?
C13 C18 1.394(3) . ?
C14 C15 1.396(3) . ?
C14 H14A 0.96(3) . ?
C15 C16 1.407(3) . ?
C15 C19 1.499(3) . ?
C16 C17 1.388(3) . ?
C17 C18 1.387(3) . ?
C17 H17A 0.92(2) . ?
C18 H18A 0.93(2) . ?
C20 H20A 0.95(3) . ?
C20 H20B 1.02(3) . ?
C20 H20C 0.91(3) . ?
C21 D21A 0.99(3) . ?
C21 D21B 0.95(3) . ?
C21 D21C 0.94(3) . ?
C22 D22A 0.96(4) . ?
C22 D22B 0.94(3) . ?
C22 D22C 1.00(3) . ?

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
O6 S1 C22 106.35(11) . . ?
O6 S1 C21 106.34(10) . . ?
C22 S1 C21 98.49(12) . . ?
C11 O3 H3A 112(2) . . ?
C16 O4 C20 117.00(16) . . ?
C5A O5 C4A 106.76(14) . . ?
C1 N2 C13 123.61(16) . . ?
C1 N2 C3 112.70(15) . . ?
C13 N2 C3 123.50(15) . . ?
O1 C1 N2 126.49(17) . . ?
O1 C1 C10A 127.59(17) . . ?
N2 C1 C10A 105.86(15) . . ?
N2 C3 C3A 100.82(15) . . ?
N2 C3 H3B 108.8(14) . . ?
C3A C3 H3B 111.3(14) . . ?
N2 C3 H3C 108.4(15) . . ?
C3A C3 H3C 115.0(16) . . ?
H3B C3 H3C 112(2) . . ?
C4 C3A C3 121.10(17) . . ?
C4 C3A C10A 108.90(15) . . ?
C3 C3A C10A 100.64(15) . . ?
C4 C3A H3AA 113.2(14) . . ?
C3 C3A H3AA 105.7(14) . . ?
C10A C3A H3AA 105.7(14) . . ?
C4A C4 C3A 110.83(17) . . ?
C4A C4 H4A 125.2(16) . . ?
C3A C4 H4A 123.9(16) . . ?
C4 C4A O5 126.55(18) . . ?
C4 C4A C9B 122.22(17) . . ?
O5 C4A C9B 111.20(16) . . ?
C6 C5A C9A 123.0(2) . . ?
C6 C5A O5 123.68(18) . . ?
C9A C5A O5 113.22(17) . . ?
C5A C6 C7 116.6(2) . . ?
C5A C6 H6A 121.1(17) . . ?
C7 C6 H6A 122.2(17) . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7A 116.7(15) . . ?
C6 C7 H7A 121.6(15) . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8A 117.8(16) . . ?
C9 C8 H8A 121.9(16) . . ?
C9A C9 C8 118.7(2) . . ?
C9A C9 H9A 123.3(18) . . ?
C8 C9 H9A 117.9(18) . . ?
C9 C9A C5A 119.81(18) . . ?
C9 C9A C9B 132.12(18) . . ?
C5A C9A C9B 107.53(17) . . ?
C9A C9B C4A 101.14(15) . . ?
C9A C9B C10 120.14(15) . . ?
C4A C9B C10 111.91(16) . . ?
C9A C9B H9BA 108.7(15) . . ?
C4A C9B H9BA 108.0(15) . . ?
C10 C9B H9BA 106.4(15) . . ?
C1 C10A C3A 102.58(14) . . ?
C1 C10A C10 119.70(15) . . ?
C3A C10A C10 114.55(15) . . ?
C1 C10A H10A 108.5(13) . . ?
C3A C10A H10A 103.7(13) . . ?
C10 C10A H10A 106.6(13) . . ?
C12 C10 C11 109.05(14) . . ?
C12 C10 C10A 108.16(15) . . ?
C11 C10 C10A 111.15(15) . . ?
C12 C10 C9B 111.70(15) . . ?
C11 C10 C9B 109.92(15) . . ?
C10A C10 C9B 106.85(14) . . ?
O2 C11 O3 125.53(17) . . ?
O2 C11 C10 123.70(16) . . ?
O3 C11 C10 110.77(15) . . ?
F1 C12 F3 107.01(15) . . ?
F1 C12 F2 106.30(15) . . ?
F3 C12 F2 106.89(15) . . ?
F1 C12 C10 114.44(16) . . ?
F3 C12 C10 111.57(15) . . ?
F2 C12 C10 110.22(15) . . ?
C14 C13 C18 119.42(17) . . ?
C14 C13 N2 120.64(17) . . ?
C18 C13 N2 119.94(17) . . ?
C13 C14 C15 120.11(17) . . ?
C13 C14 H14A 123.9(15) . . ?
C15 C14 H14A 116.0(16) . . ?
C14 C15 C16 120.17(17) . . ?
C14 C15 C19 119.96(17) . . ?
C16 C15 C19 119.85(17) . . ?
O4 C16 C17 124.23(17) . . ?
O4 C16 C15 116.57(17) . . ?
C17 C16 C15 119.20(17) . . ?
C18 C17 C16 120.35(18) . . ?
C18 C17 H17A 118.0(15) . . ?
C16 C17 H17A 121.6(15) . . ?
C17 C18 C13 120.73(18) . . ?
C17 C18 H18A 120.4(14) . . ?
C13 C18 H18A 118.8(14) . . ?
F6 C19 F4 106.80(16) . . ?
F6 C19 F5 106.52(16) . . ?
F4 C19 F5 106.48(16) . . ?
F6 C19 C15 112.69(16) . . ?
F4 C19 C15 112.16(16) . . ?
F5 C19 C15 111.77(16) . . ?
O4 C20 H20A 108.4(16) . . ?
O4 C20 H20B 113.2(16) . . ?
H20A C20 H20B 108(2) . . ?
O4 C20 H20C 109.3(17) . . ?
H20A C20 H20C 108(2) . . ?
H20B C20 H20C 110(2) . . ?
S1 C21 D21A 106.5(18) . . ?
S1 C21 D21B 106.3(18) . . ?
D21A C21 D21B 105(2) . . ?
S1 C21 D21C 109.0(18) . . ?
D21A C21 D21C 118(2) . . ?
D21B C21 D21C 111(3) . . ?
S1 C22 D22A 107(2) . . ?
S1 C22 D22B 108.6(18) . . ?
D22A C22 D22B 109(3) . . ?
S1 C22 D22C 107.0(17) . . ?
D22A C22 D22C 112(3) . . ?
D22B C22 D22C 113(2) . . ?

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
C13 N2 C1 O1 0.9(3) . . . . ?
C3 N2 C1 O1 176.06(19) . . . . ?
C13 N2 C1 C10A -176.70(16) . . . . ?
C3 N2 C1 C10A -1.5(2) . . . . ?
C1 N2 C3 C3A 26.5(2) . . . . ?
C13 N2 C3 C3A -158.37(17) . . . . ?
N2 C3 C3A C4 -158.79(16) . . . . ?
N2 C3 C3A C10A -38.91(17) . . . . ?
C3 C3A C4 C4A 167.19(18) . . . . ?
C10A C3A C4 C4A 51.4(2) . . . . ?
C3A C4 C4A O5 -178.86(17) . . . . ?
C3A C4 C4A C9B 3.2(3) . . . . ?
C5A O5 C4A C4 -177.1(2) . . . . ?
C5A O5 C4A C9B 1.1(2) . . . . ?
C4A O5 C5A C6 173.51(19) . . . . ?
C4A O5 C5A C9A -3.3(2) . . . . ?
C9A C5A C6 C7 -0.1(3) . . . . ?
O5 C5A C6 C7 -176.66(19) . . . . ?
C5A C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C9 1.7(3) . . . . ?
C7 C8 C9 C9A -1.9(3) . . . . ?
C8 C9 C9A C5A 1.2(3) . . . . ?
C8 C9 C9A C9B 171.6(2) . . . . ?
C6 C5A C9A C9 -0.2(3) . . . . ?
O5 C5A C9A C9 176.71(18) . . . . ?
C6 C5A C9A C9B -172.71(19) . . . . ?
O5 C5A C9A C9B 4.2(2) . . . . ?
C9 C9A C9B C4A -174.4(2) . . . . ?
C5A C9A C9B C4A -3.1(2) . . . . ?
C9 C9A C9B C10 62.0(3) . . . . ?
C5A C9A C9B C10 -126.74(18) . . . . ?
C4 C4A C9B C9A 179.47(18) . . . . ?
O5 C4A C9B C9A 1.2(2) . . . . ?
C4 C4A C9B C10 -51.4(2) . . . . ?
O5 C4A C9B C10 130.33(16) . . . . ?
O1 C1 C10A C3A 158.51(19) . . . . ?
N2 C1 C10A C3A -23.92(18) . . . . ?
O1 C1 C10A C10 30.4(3) . . . . ?
N2 C1 C10A C10 -152.04(16) . . . . ?
C4 C3A C10A C1 167.23(16) . . . . ?
C3 C3A C10A C1 38.92(17) . . . . ?
C4 C3A C10A C10 -61.5(2) . . . . ?
C3 C3A C10A C10 170.22(15) . . . . ?
C1 C10A C10 C12 -102.95(18) . . . . ?
C3A C10A C10 C12 134.63(16) . . . . ?
C1 C10A C10 C11 16.7(2) . . . . ?
C3A C10A C10 C11 -105.69(17) . . . . ?
C1 C10A C10 C9B 136.66(16) . . . . ?
C3A C10A C10 C9B 14.2(2) . . . . ?
C9A C9B C10 C12 37.0(2) . . . . ?
C4A C9B C10 C12 -81.29(19) . . . . ?
C9A C9B C10 C11 -84.2(2) . . . . ?
C4A C9B C10 C11 157.52(15) . . . . ?
C9A C9B C10 C10A 155.12(16) . . . . ?
C4A C9B C10 C10A 36.8(2) . . . . ?
C12 C10 C11 O2 5.1(2) . . . . ?
C10A C10 C11 O2 -114.1(2) . . . . ?
C9B C10 C11 O2 127.85(19) . . . . ?
C12 C10 C11 O3 -175.23(16) . . . . ?
C10A C10 C11 O3 65.62(19) . . . . ?
C9B C10 C11 O3 -52.5(2) . . . . ?
C11 C10 C12 F1 54.4(2) . . . . ?
C10A C10 C12 F1 175.39(15) . . . . ?
C9B C10 C12 F1 -67.3(2) . . . . ?
C11 C10 C12 F3 -67.29(19) . . . . ?
C10A C10 C12 F3 53.71(19) . . . . ?
C9B C10 C12 F3 171.02(14) . . . . ?
C11 C10 C12 F2 174.13(15) . . . . ?
C10A C10 C12 F2 -64.88(18) . . . . ?
C9B C10 C12 F2 52.4(2) . . . . ?
C1 N2 C13 C14 137.86(19) . . . . ?
C3 N2 C13 C14 -36.8(3) . . . . ?
C1 N2 C13 C18 -42.5(3) . . . . ?
C3 N2 C13 C18 142.88(19) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
N2 C13 C14 C15 179.07(17) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C13 C14 C15 C19 178.13(18) . . . . ?
C20 O4 C16 C17 -10.2(3) . . . . ?
C20 O4 C16 C15 169.95(17) . . . . ?
C14 C15 C16 O4 -178.46(17) . . . . ?
C19 C15 C16 O4 2.7(3) . . . . ?
C14 C15 C16 C17 1.7(3) . . . . ?
C19 C15 C16 C17 -177.12(18) . . . . ?
O4 C16 C17 C18 178.75(18) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C14 C13 C18 C17 0.9(3) . . . . ?
N2 C13 C18 C17 -178.79(17) . . . . ?
C14 C15 C19 F6 119.85(19) . . . . ?
C16 C15 C19 F6 -61.3(2) . . . . ?
C14 C15 C19 F4 -0.7(3) . . . . ?
C16 C15 C19 F4 178.12(16) . . . . ?
C14 C15 C19 F5 -120.22(19) . . . . ?
C16 C15 C19 F5 58.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O6 0.96(4) 1.55(4) 2.506(2) 173(4) . yes

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046


# start Validation Reply Form
_vrf_PLAT035_zv2108              
;
PROBLEM: _chemical_absolute_configuration Info Not Given Please Do !
RESPONSE: ...
;
_vrf_PLAT910_zv2108              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
