# 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_VM-AK-THF-EtOH
_database_code_depnum_ccdc_archive 'CCDC 2448540'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-05-04 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_audit_creation_date             2025-03-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 F N3 O3'
_chemical_formula_sum            'C21 H16 F N3 O3'
_chemical_formula_weight         377.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H20N3O3F1
_chemical_oxdiff_usercomment     VM-AK-THF-EtOH
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'

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

_cell_length_a                   9.28605(11)
_cell_length_b                   14.2749(3)
_cell_length_c                   14.7953(3)
_cell_angle_alpha                63.9662(18)
_cell_angle_beta                 89.9415(12)
_cell_angle_gamma                81.1842(13)
_cell_volume                     1736.55(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25197
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      79.9380
_cell_measurement_theta_min      4.8180
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    0.882
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.99a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0973
0 0 -1 0.0798
0 1 0 0.0102
0 -1 0 0.0222
-1 0 0 0.2777
-1 4 9 0.1025
-2 -3 -9 0.0824
5 3 5 0.2063
5 -3 -3 0.2164

_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -0.0005 1.0001 0.0426 -0.1056 -0.0233
-0.0000 0.0005 -1.0001 -0.0426 0.1056 0.0233
-0.0000 1.0005 0.0007 0.0793 0.0821 0.0428
0.0000 -1.0005 -0.0007 -0.0793 -0.0821 -0.0428
-1.0003 -0.0006 -0.0002 -0.0154 -0.0288 0.1652
-1.3918 4.2405 9.3133 0.7119 -0.6749 0.1944
-2.1532 -3.0965 -8.8696 -0.6566 0.6199 0.4297
5.1134 2.5575 5.0136 0.4947 -0.1719 -0.8519
5.3447 -2.8859 -2.7312 -0.2633 0.2052 -0.9426

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13773
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.035
_diffrn_reflns_theta_min         3.334
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -2.00   0.50    1.20    --  -40.70 111.00 -21.00  160
  2  ω     24.00  88.00   0.50    1.20    --   40.70-111.00-114.00  128
  3  ω    -82.00 -23.00   0.50    4.80    --  -98.00 111.00 -21.00  118
  4  ω   -173.00 -81.00   0.50    4.80    --  -98.00-111.00-114.00  184
  5  ω    103.00 178.00   0.50    4.80    --  119.50 111.00 -21.00  150
  6  ω     44.00 108.00   0.50    4.80    --  119.50-111.00-114.00  128
  7  ω   -115.00 -15.00   0.50    1.20    --  -40.70 -57.00-150.00  200
  8  ω    -43.00  39.00   0.50    1.20    --  -40.70  38.00  90.00  164
  9  ω    -43.00  39.00   0.50    1.20    --  -40.70  38.00-150.00  164
 10  ω    -27.00  42.00   0.50    1.20    --  -40.70  19.00   0.00  138
 11  ω   -115.00 -15.00   0.50    1.20    --  -40.70 -57.00-150.00  200
 12  ω    -43.00  39.00   0.50    1.20    --  -40.70  38.00 150.00  164
 13  ω    -43.00  39.00   0.50    1.20    --  -40.70  38.00 150.00  164
 14  ω     63.00 123.00   0.50    1.20    --   40.70 178.00   0.00  120
 15  ω     61.00 123.00   0.50    1.20    --   40.70-178.00  60.00  124
 16  ω   -172.00 -69.00   0.50    4.80    --  -98.00 -67.00 -38.30  206
 17  ω   -172.00 -69.00   0.50    4.80    --  -98.00 -67.00 -38.30  206
 18  ω    -71.00 -23.00   0.50    4.80    --  -98.00  61.00-180.00   96
 19  ω    -71.00 -23.00   0.50    4.80    --  -98.00  61.00  90.00   96
 20  ω    -51.00 -20.00   0.50    4.80    --  -98.00  45.00 -60.00   62
 21  ω    -82.00 -23.00   0.50    4.80    --  -98.00 111.00 -21.00  118
 22  ω     93.00 178.00   0.50    4.80    --  119.50  61.00  60.00  170
 23  ω     61.00 151.00   0.50    4.80    --  119.50-178.00  90.00  180
 24  ω     44.00 108.00   0.50    4.80    --  119.50-111.00 -30.00  128
 25  ω     41.00 105.00   0.50    4.80    --  119.50 -95.00   0.00  128
 26  ω     93.00 178.00   0.50    4.80    --  119.50  45.00-180.00  170
 27  ω     46.00 105.00   0.50    4.80    --  119.50 -77.00-180.00  118
 28  ω    103.00 178.00   0.50    4.80    --  119.50 111.00 -60.00  150
 29  ω     41.00 105.00   0.50    4.80    --  119.50 -95.00-150.00  128
 30  ω     93.00 178.00   0.50    4.80    --  119.50  61.00 -60.00  170
 31  ω     93.00 178.00   0.50    4.80    --  119.50  61.00-120.00  170
 32  ω     93.00 178.00   0.50    4.80    --  119.50  61.00-120.00  170
 33  ω     45.00 155.00   0.50    4.80    --  119.50 -83.00 123.86  220
 34  ω     93.00 178.00   0.50    4.80    --  119.50  45.00 150.00  170
 35  ω     93.00 178.00   0.50    4.80    --  119.50  45.00 150.00  170
 36  ω     41.00 105.00   0.50    4.80    --  119.50 -95.00 120.00  128
 37  ω     93.00 178.00   0.50    4.80    --  119.50  61.00 120.00  170
 38  ω     41.00 105.00   0.50    4.80    --  119.50 -95.00  60.00  128
 39  ω     93.00 178.00   0.50    4.80    --  119.50  61.00   0.00  170
 40  ω     44.00 108.00   0.50    4.80    --  119.50-111.00 120.00  128
 41  ω     41.00 105.00   0.50    4.80    --  119.50 -95.00  30.00  128
 42  ω     87.00 178.00   0.50    4.80    --  119.50  30.00 120.00  182
 43  ω     46.00 105.00   0.50    4.80    --  119.50 -77.00  30.00  118
 44  ω     45.00 155.00   0.50    4.80    --  119.50 -83.00 -37.97  220
 45  ω    103.00 178.00   0.50    4.80    --  119.50 111.00 -30.00  150
 46  ω     42.00 178.00   0.50    4.80    --  119.50  15.00 -60.00  272
 47  ω     44.00 108.00   0.50    4.80    --  119.50-111.00  30.00  128
 48  ω     41.00 105.00   0.50    4.80    --  119.50 -95.00  60.00  128
 49  ω     46.00 105.00   0.50    4.80    --  119.50 -77.00 120.00  118
 50  ω     93.00 178.00   0.50    4.80    --  119.50  61.00 120.00  170
 51  ω     44.00 108.00   0.50    4.80    --  119.50-111.00 -90.00  128
 52  ω     93.00 178.00   0.50    4.80    --  119.50  45.00-180.00  170
 53  ω     46.00 105.00   0.50    4.80    --  119.50 -77.00 -90.00  118
 54  ω     93.00 178.00   0.50    4.80    --  119.50  45.00  90.00  170
 55  ω     87.00 178.00   0.50    4.80    --  119.50  77.00-150.00  182
 56  ω     63.00 146.00   0.50    4.80    --  119.50 178.00  60.00  166
 57  ω     63.00 146.00   0.50    4.80    --  119.50 178.00  60.00  166
 58  ω     63.00 146.00   0.50    4.80    --  119.50 178.00 120.00  166
 59  ω     93.00 178.00   0.50    4.80    --  119.50  45.00 -30.00  170
 60  ω     61.00 151.00   0.50    4.80    --  119.50-178.00  30.00  180
 61  ω     87.00 178.00   0.50    4.80    --  119.50  30.00 120.00  182
 62  ω    103.00 178.00   0.50    4.80    --  119.50 111.00 120.00  150
 63  ω    103.00 178.00   0.50    4.80    --  119.50 111.00 150.00  150
 64  ω     61.00 151.00   0.50    4.80    --  119.50-178.00-120.00  180
 65  ω     61.00 151.00   0.50    4.80    --  119.50-178.00 -90.00  180
 66  ω     61.00 151.00   0.50    4.80    --  119.50-178.00   0.00  180
 67  ω     96.00 148.00   0.50    4.80    --  119.50-178.00   0.00  104
 68  ω     58.00  84.00   0.50    4.80    --  119.50 -95.00-180.00   52
 69  ω     96.00 157.00   0.50    4.80    --  119.50  61.00 -30.00  122
 70  ω     50.00  76.00   0.50    4.80    --  119.50-111.00-120.00   52
 71  ω     79.00 106.00   0.50    4.80    --  119.50-111.00-150.00   54
 72  ω     90.00 157.00   0.50    4.80    --  119.50  30.00 -60.00  134
 73  ω     45.00  75.00   0.50    4.80    --  119.50-111.00  90.00   60
 74  ω     80.00 106.00   0.50    4.80    --  119.50-111.00  90.00   52
 75  ω     46.00  80.00   0.50    4.80    --  119.50 -77.00 -30.00   68
 76  ω     96.00 123.00   0.50    4.80    --  119.50  61.00  90.00   54
 77  ω     47.00  79.00   0.50    4.80    --  119.50 -77.00-120.00   64
 78  ω    107.00 153.00   0.50    4.80    --  119.50 111.00-180.00   92
 79  ω    103.00 129.00   0.50    4.80    --  119.50-178.00 120.00   52
 80  ω     95.00 130.00   0.50    4.80    --  119.50  77.00  90.00   70
 81  ω     87.00 178.00   0.50    4.80    --  119.50  30.00-150.00  182
 82  ω    121.00 148.00   0.50    4.80    --  119.50 -80.00 -41.72   54
 83  ω    117.00 143.00   0.50    4.80    --  119.50 -85.00 -34.82   52
 84  ω     60.00  86.00   0.50    4.80    --  119.50 -84.00 111.67   52
 85  ω    116.00 150.00   0.50    4.80    --  119.50 -84.00 111.67   68
 86  ω    102.00 128.00   0.50    4.80    --  119.50  15.00 -60.00   52
 87  ω     69.00 108.00   0.50    4.80    --  119.50-111.00-180.00   78
 88  ω     81.00 107.00   0.50    4.80    --  119.50-111.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0153087000
_diffrn_orient_matrix_UB_12      0.0792264000
_diffrn_orient_matrix_UB_13      0.0426500000
_diffrn_orient_matrix_UB_21      0.0287989000
_diffrn_orient_matrix_UB_22      0.0821424000
_diffrn_orient_matrix_UB_23      -0.1055590000
_diffrn_orient_matrix_UB_31      -0.1651638000
_diffrn_orient_matrix_UB_32      0.0427947000
_diffrn_orient_matrix_UB_33      -0.0232900000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12677
_reflns_number_total             13773
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.44.99a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 44.99a 64-bit (release 17-03-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.99a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         13773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0930P)²+0.2767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6839(8)
 0.3161(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C13A(H13A), C14A(H14A), C16A(H16A), C17A(H17A), C20A(H20A),
 C21A(H21A), C22A(H22A), C23A(H23A), C24A(H24A), C7B(H7B), C13B(H13B),
 C14B(H14B), C16B(H16B), C17B(H17B), C20B(H20B), C21B(H21B), C22B(H22B),
 C23B(H23B), C24B(H24B)
3.b Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
F1A F 0.39355(12) -0.06205(8) 0.90866(9) 0.0381(2) Uani 1 1 d . . . . .
O5A O 0.09253(10) 0.39279(8) 0.94931(7) 0.0201(2) Uani 1 1 d . . . . .
H5A H 0.046(4) 0.416(3) 0.886(3) 0.082(10) Uiso 1 1 d . . . . .
O8A O 0.28694(14) 0.62568(11) 1.03082(9) 0.0340(3) Uani 1 1 d . . . . .
O9A O 0.06594(10) 0.60540(9) 0.90163(8) 0.0207(2) Uani 1 1 d . . . . .
H9A H 0.022(4) 0.602(2) 0.958(2) 0.071(9) Uiso 1 1 d . . . . .
N1A N 0.43683(12) 0.52770(9) 0.72933(9) 0.0184(2) Uani 1 1 d . . . . .
N2A N 0.45858(12) 0.42387(9) 0.74504(9) 0.0185(2) Uani 1 1 d . . . . .
H2A H 0.503(3) 0.4096(18) 0.7007(18) 0.037(6) Uiso 1 1 d . . . . .
N10A N 0.29153(12) 0.60357(10) 0.82983(9) 0.0188(2) Uani 1 1 d . . . . .
C3A C 0.38758(13) 0.36061(11) 0.82227(10) 0.0179(3) Uani 1 1 d . . . . .
C4A C 0.31490(13) 0.42656(11) 0.86044(10) 0.0175(3) Uani 1 1 d . . . . .
C5A C 0.22760(13) 0.43018(11) 0.94355(10) 0.0177(3) Uani 1 1 d . . . . .
C6A C 0.31308(14) 0.37285(12) 1.04629(10) 0.0227(3) Uani 1 1 d . . . . .
C7A C 0.34405(14) 0.43921(13) 1.08256(11) 0.0248(3) Uani 1 1 d . . . . .
H7A H 0.399120 0.416986 1.144692 0.030 Uiso 1 1 calc R U . . .
C8A C 0.28406(14) 0.54873(13) 1.01629(11) 0.0233(3) Uani 1 1 d . . . . .
C9A C 0.20949(14) 0.55263(11) 0.91995(10) 0.0185(3) Uani 1 1 d . . . . .
C11A C 0.34815(13) 0.52639(11) 0.80037(10) 0.0171(3) Uani 1 1 d . . . . .
C12A C 0.39123(14) 0.24930(11) 0.84588(10) 0.0192(3) Uani 1 1 d . . . . .
C13A C 0.50603(15) 0.19333(12) 0.81847(11) 0.0237(3) Uani 1 1 d . . . . .
H13A H 0.583886 0.227722 0.785150 0.028 Uiso 1 1 calc R U . . .
C14A C 0.50785(16) 0.08841(13) 0.83922(12) 0.0273(3) Uani 1 1 d . . . . .
H14A H 0.585882 0.050723 0.820482 0.033 Uiso 1 1 calc R U . . .
C15A C 0.39347(17) 0.04013(12) 0.88778(12) 0.0272(3) Uani 1 1 d . . . . .
C16A C 0.27844(16) 0.09246(13) 0.91602(13) 0.0289(3) Uani 1 1 d . . . . .
H16A H 0.201353 0.057235 0.949607 0.035 Uiso 1 1 calc R U . . .
C17A C 0.27731(15) 0.19758(12) 0.89447(12) 0.0249(3) Uani 1 1 d . . . . .
H17A H 0.198257 0.234725 0.912967 0.030 Uiso 1 1 calc R U . . .
C18A C 0.35673(19) 0.25589(14) 1.09386(12) 0.0329(3) Uani 1 1 d . . . . .
H18A H 0.269429 0.222948 1.101781 0.049 Uiso 1 1 calc R U . . .
H18B H 0.407588 0.232013 1.160199 0.049 Uiso 1 1 calc R U . . .
H18C H 0.421968 0.235584 1.050978 0.049 Uiso 1 1 calc R U . . .
C19A C 0.25515(13) 0.71294(11) 0.76133(11) 0.0206(3) Uani 1 1 d . . . . .
C20A C 0.23334(15) 0.74419(12) 0.65808(12) 0.0233(3) Uani 1 1 d . . . . .
H20A H 0.243931 0.692586 0.633260 0.028 Uiso 1 1 calc R U . . .
C21A C 0.19596(17) 0.85136(13) 0.59138(13) 0.0288(3) Uani 1 1 d . . . . .
H21A H 0.181890 0.872405 0.521098 0.035 Uiso 1 1 calc R U . . .
C22A C 0.17915(17) 0.92755(13) 0.62681(14) 0.0315(3) Uani 1 1 d . . . . .
H22A H 0.152575 1.000374 0.581246 0.038 Uiso 1 1 calc R U . . .
C23A C 0.20163(17) 0.89606(13) 0.72967(14) 0.0314(3) Uani 1 1 d . . . . .
H23A H 0.190698 0.947882 0.754230 0.038 Uiso 1 1 calc R U . . .
C24A C 0.23997(15) 0.78945(13) 0.79716(12) 0.0261(3) Uani 1 1 d . . . . .
H24A H 0.255751 0.768814 0.867246 0.031 Uiso 1 1 calc R U . . .
F1B F 0.59959(12) 1.06049(8) 0.62833(9) 0.0383(2) Uani 1 1 d . . . . .
O5B O 0.53281(10) 0.62311(8) 0.54334(7) 0.0186(2) Uani 1 1 d . . . . .
H5B H 0.499(3) 0.602(2) 0.608(2) 0.047(6) Uiso 1 1 d . . . . .
O8B O 0.83551(13) 0.40450(10) 0.44870(10) 0.0314(3) Uani 1 1 d . . . . .
O9B O 0.61543(10) 0.41150(8) 0.58998(7) 0.0193(2) Uani 1 1 d . . . . .
H9B H 0.581(3) 0.4021(19) 0.538(2) 0.043(6) Uiso 1 1 d . . . . .
N1B N 0.94684(12) 0.48904(9) 0.76058(9) 0.0183(2) Uani 1 1 d . . . . .
N2B N 0.91578(12) 0.59055(9) 0.75067(9) 0.0190(2) Uani 1 1 d . . . . .
H2B H 0.959(3) 0.603(2) 0.801(2) 0.049(7) Uiso 1 1 d . . . . .
N10B N 0.84266(12) 0.41752(9) 0.65432(9) 0.0187(2) Uani 1 1 d . . . . .
C3B C 0.81154(13) 0.65314(11) 0.67582(10) 0.0182(3) Uani 1 1 d . . . . .
C4B C 0.77203(13) 0.59019(11) 0.63347(10) 0.0173(2) Uani 1 1 d . . . . .
C5B C 0.68586(13) 0.58897(11) 0.54894(10) 0.0172(3) Uani 1 1 d . . . . .
C6B C 0.74098(14) 0.65158(12) 0.44621(10) 0.0206(3) Uani 1 1 d . . . . .
C7B C 0.80434(14) 0.58937(13) 0.40569(11) 0.0226(3) Uani 1 1 d . . . . .
H7B H 0.848137 0.615005 0.343177 0.027 Uiso 1 1 calc R U . . .
C8B C 0.79833(14) 0.47806(12) 0.46847(11) 0.0212(3) Uani 1 1 d . . . . .
C9B C 0.73064(13) 0.46806(11) 0.56767(10) 0.0177(3) Uani 1 1 d . . . . .
C11B C 0.85807(13) 0.49149(11) 0.68864(10) 0.0169(2) Uani 1 1 d . . . . .
C12B C 0.75769(15) 0.76182(11) 0.65909(11) 0.0202(3) Uani 1 1 d . . . . .
C13B C 0.84803(15) 0.81822(12) 0.68392(13) 0.0269(3) Uani 1 1 d . . . . .
H13B H 0.946818 0.787250 0.708090 0.032 Uiso 1 1 calc R U . . .
C14B C 0.79501(18) 0.91875(13) 0.67364(15) 0.0326(3) Uani 1 1 d . . . . .
H14B H 0.856557 0.957190 0.690216 0.039 Uiso 1 1 calc R U . . .
C15B C 0.65154(17) 0.96183(12) 0.63898(13) 0.0275(3) Uani 1 1 d . . . . .
C16B C 0.55880(15) 0.90883(12) 0.61387(12) 0.0260(3) Uani 1 1 d . . . . .
H16B H 0.459939 0.940424 0.590516 0.031 Uiso 1 1 calc R U . . .
C17B C 0.61241(15) 0.80858(12) 0.62330(11) 0.0227(3) Uani 1 1 d . . . . .
H17B H 0.550267 0.771397 0.605399 0.027 Uiso 1 1 calc R U . . .
C18B C 0.72335(17) 0.76876(12) 0.40245(12) 0.0281(3) Uani 1 1 d . . . . .
H18D H 0.619416 0.798714 0.395660 0.042 Uiso 1 1 calc R U . . .
H18E H 0.762621 0.796362 0.335907 0.042 Uiso 1 1 calc R U . . .
H18F H 0.776386 0.788453 0.446943 0.042 Uiso 1 1 calc R U . . .
C19B C 0.86746(14) 0.30695(11) 0.71862(12) 0.0217(3) Uani 1 1 d . . . . .
C20B C 0.85916(16) 0.26927(12) 0.82253(13) 0.0265(3) Uani 1 1 d . . . . .
H20B H 0.837095 0.317608 0.850780 0.032 Uiso 1 1 calc R U . . .
C21B C 0.88324(18) 0.16064(14) 0.88495(15) 0.0354(4) Uani 1 1 d . . . . .
H21B H 0.877119 0.135074 0.955681 0.042 Uiso 1 1 calc R U . . .
C22B C 0.91610(19) 0.08984(13) 0.84404(17) 0.0406(4) Uani 1 1 d . . . . .
H22B H 0.932709 0.015814 0.886473 0.049 Uiso 1 1 calc R U . . .
C23B C 0.9245(2) 0.12797(14) 0.74074(18) 0.0405(4) Uani 1 1 d . . . . .
H23B H 0.947342 0.079420 0.712801 0.049 Uiso 1 1 calc R U . . .
C24B C 0.90022(17) 0.23590(14) 0.67731(14) 0.0318(3) Uani 1 1 d . . . . .
H24B H 0.905848 0.261007 0.606586 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
F1A C15A 1.3517(17) . ?
O5A H5A 0.93(4) . ?
O5A C5A 1.4250(15) . ?
O8A C8A 1.212(2) . ?
O9A H9A 0.91(3) . ?
O9A C9A 1.3898(15) . ?
N1A N2A 1.3774(16) . ?
N1A C11A 1.3300(17) . ?
N2A H2A 0.86(2) . ?
N2A C3A 1.3531(17) . ?
N10A C9A 1.4845(17) . ?
N10A C11A 1.3870(17) . ?
N10A C19A 1.4244(19) . ?
C3A C4A 1.3900(18) . ?
C3A C12A 1.4642(19) . ?
C4A C5A 1.4875(17) . ?
C4A C11A 1.3923(19) . ?
C5A C6A 1.5238(18) . ?
C5A C9A 1.6062(19) . ?
C6A C7A 1.341(2) . ?
C6A C18A 1.486(2) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.451(2) . ?
C8A C9A 1.5604(18) . ?
C12A C13A 1.4006(18) . ?
C12A C17A 1.3975(19) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.388(2) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.381(2) . ?
C15A C16A 1.379(2) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.389(2) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A C20A 1.396(2) . ?
C19A C24A 1.3980(19) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.395(2) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.389(2) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.390(3) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.393(2) . ?
C24A H24A 0.9500 . ?
F1B C15B 1.3559(17) . ?
O5B H5B 0.94(3) . ?
O5B C5B 1.4202(15) . ?
O8B C8B 1.2107(19) . ?
O9B H9B 0.90(3) . ?
O9B C9B 1.3912(15) . ?
N1B N2B 1.3747(16) . ?
N1B C11B 1.3319(17) . ?
N2B H2B 0.95(3) . ?
N2B C3B 1.3528(18) . ?
N10B C9B 1.4855(16) . ?
N10B C11B 1.3821(17) . ?
N10B C19B 1.4215(18) . ?
C3B C4B 1.3894(18) . ?
C3B C12B 1.4641(19) . ?
C4B C5B 1.4933(18) . ?
C4B C11B 1.3916(18) . ?
C5B C6B 1.5222(18) . ?
C5B C9B 1.6091(19) . ?
C6B C7B 1.342(2) . ?
C6B C18B 1.486(2) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.457(2) . ?
C8B C9B 1.5529(18) . ?
C12B C13B 1.3978(19) . ?
C12B C17B 1.4004(19) . ?
C13B H13B 0.9500 . ?
C13B C14B 1.385(2) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.375(2) . ?
C15B C16B 1.378(2) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.386(2) . ?
C17B H17B 0.9500 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B C20B 1.395(2) . ?
C19B C24B 1.394(2) . ?
C20B H20B 0.9500 . ?
C20B C21B 1.394(2) . ?
C21B H21B 0.9500 . ?
C21B C22B 1.387(3) . ?
C22B H22B 0.9500 . ?
C22B C23B 1.386(3) . ?
C23B H23B 0.9500 . ?
C23B C24B 1.389(3) . ?
C24B H24B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5A O5A H5A 112(2) . . ?
C9A O9A H9A 115(2) . . ?
C11A N1A N2A 102.40(11) . . ?
N1A N2A H2A 117.2(15) . . ?
C3A N2A N1A 113.98(11) . . ?
C3A N2A H2A 128.0(15) . . ?
C11A N10A C9A 107.38(11) . . ?
C11A N10A C19A 123.21(11) . . ?
C19A N10A C9A 122.51(11) . . ?
N2A C3A C4A 104.95(12) . . ?
N2A C3A C12A 121.40(12) . . ?
C4A C3A C12A 133.54(12) . . ?
C3A C4A C5A 144.70(13) . . ?
C3A C4A C11A 105.44(11) . . ?
C11A C4A C5A 109.58(11) . . ?
O5A C5A C4A 114.01(11) . . ?
O5A C5A C6A 109.52(11) . . ?
O5A C5A C9A 113.88(10) . . ?
C4A C5A C6A 112.95(10) . . ?
C4A C5A C9A 102.43(10) . . ?
C6A C5A C9A 103.46(11) . . ?
C7A C6A C5A 112.69(13) . . ?
C7A C6A C18A 127.10(14) . . ?
C18A C6A C5A 120.18(13) . . ?
C6A C7A H7A 123.8 . . ?
C6A C7A C8A 112.45(13) . . ?
C8A C7A H7A 123.8 . . ?
O8A C8A C7A 127.84(14) . . ?
O8A C8A C9A 124.16(14) . . ?
C7A C8A C9A 107.99(12) . . ?
O9A C9A N10A 109.62(11) . . ?
O9A C9A C5A 114.79(10) . . ?
O9A C9A C8A 111.20(11) . . ?
N10A C9A C5A 106.05(10) . . ?
N10A C9A C8A 111.67(10) . . ?
C8A C9A C5A 103.31(11) . . ?
N1A C11A N10A 132.10(13) . . ?
N1A C11A C4A 113.21(12) . . ?
N10A C11A C4A 114.51(12) . . ?
C13A C12A C3A 121.15(12) . . ?
C17A C12A C3A 120.13(12) . . ?
C17A C12A C13A 118.70(13) . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A C12A 121.05(13) . . ?
C14A C13A H13A 119.5 . . ?
C13A C14A H14A 120.8 . . ?
C15A C14A C13A 118.39(13) . . ?
C15A C14A H14A 120.8 . . ?
F1A C15A C14A 119.18(14) . . ?
F1A C15A C16A 118.48(14) . . ?
C16A C15A C14A 122.34(14) . . ?
C15A C16A H16A 120.6 . . ?
C15A C16A C17A 118.81(14) . . ?
C17A C16A H16A 120.6 . . ?
C12A C17A H17A 119.6 . . ?
C16A C17A C12A 120.70(13) . . ?
C16A C17A H17A 119.6 . . ?
C6A C18A H18A 109.5 . . ?
C6A C18A H18B 109.5 . . ?
C6A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C20A C19A N10A 120.10(12) . . ?
C20A C19A C24A 119.67(14) . . ?
C24A C19A N10A 120.23(13) . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 119.90(14) . . ?
C21A C20A H20A 120.0 . . ?
C20A C21A H21A 119.7 . . ?
C22A C21A C20A 120.60(16) . . ?
C22A C21A H21A 119.7 . . ?
C21A C22A H22A 120.4 . . ?
C21A C22A C23A 119.28(15) . . ?
C23A C22A H22A 120.4 . . ?
C22A C23A H23A 119.6 . . ?
C22A C23A C24A 120.81(15) . . ?
C24A C23A H23A 119.6 . . ?
C19A C24A H24A 120.1 . . ?
C23A C24A C19A 119.73(15) . . ?
C23A C24A H24A 120.1 . . ?
C5B O5B H5B 111.0(16) . . ?
C9B O9B H9B 113.8(16) . . ?
C11B N1B N2B 103.22(11) . . ?
N1B N2B H2B 116.7(16) . . ?
C3B N2B N1B 112.80(11) . . ?
C3B N2B H2B 129.8(16) . . ?
C11B N10B C9B 107.72(11) . . ?
C11B N10B C19B 122.60(12) . . ?
C19B N10B C9B 122.44(11) . . ?
N2B C3B C4B 106.10(12) . . ?
N2B C3B C12B 120.17(12) . . ?
C4B C3B C12B 133.59(12) . . ?
C3B C4B C5B 145.16(13) . . ?
C3B C4B C11B 104.84(12) . . ?
C11B C4B C5B 109.67(12) . . ?
O5B C5B C4B 115.45(11) . . ?
O5B C5B C6B 108.27(11) . . ?
O5B C5B C9B 113.92(10) . . ?
C4B C5B C6B 112.95(11) . . ?
C4B C5B C9B 102.15(10) . . ?
C6B C5B C9B 103.46(10) . . ?
C7B C6B C5B 112.62(13) . . ?
C7B C6B C18B 127.29(13) . . ?
C18B C6B C5B 120.08(12) . . ?
C6B C7B H7B 123.8 . . ?
C6B C7B C8B 112.32(13) . . ?
C8B C7B H7B 123.8 . . ?
O8B C8B C7B 127.71(14) . . ?
O8B C8B C9B 124.33(13) . . ?
C7B C8B C9B 107.94(12) . . ?
O9B C9B N10B 109.14(11) . . ?
O9B C9B C5B 114.36(10) . . ?
O9B C9B C8B 112.62(11) . . ?
N10B C9B C5B 105.87(10) . . ?
N10B C9B C8B 111.17(10) . . ?
C8B C9B C5B 103.42(10) . . ?
N1B C11B N10B 132.36(12) . . ?
N1B C11B C4B 113.04(12) . . ?
N10B C11B C4B 114.43(12) . . ?
C13B C12B C3B 120.50(12) . . ?
C13B C12B C17B 119.03(13) . . ?
C17B C12B C3B 120.37(12) . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B C12B 120.68(13) . . ?
C14B C13B H13B 119.7 . . ?
C13B C14B H14B 120.7 . . ?
C15B C14B C13B 118.68(14) . . ?
C15B C14B H14B 120.7 . . ?
F1B C15B C14B 118.78(14) . . ?
F1B C15B C16B 118.75(14) . . ?
C14B C15B C16B 122.47(14) . . ?
C15B C16B H16B 120.6 . . ?
C15B C16B C17B 118.79(13) . . ?
C17B C16B H16B 120.6 . . ?
C12B C17B H17B 119.8 . . ?
C16B C17B C12B 120.35(13) . . ?
C16B C17B H17B 119.8 . . ?
C6B C18B H18D 109.5 . . ?
C6B C18B H18E 109.5 . . ?
C6B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C20B C19B N10B 120.43(13) . . ?
C24B C19B N10B 119.64(14) . . ?
C24B C19B C20B 119.93(14) . . ?
C19B C20B H20B 120.0 . . ?
C21B C20B C19B 120.00(16) . . ?
C21B C20B H20B 120.0 . . ?
C20B C21B H21B 119.9 . . ?
C22B C21B C20B 120.17(18) . . ?
C22B C21B H21B 119.9 . . ?
C21B C22B H22B 120.3 . . ?
C23B C22B C21B 119.45(16) . . ?
C23B C22B H22B 120.3 . . ?
C22B C23B H23B 119.4 . . ?
C22B C23B C24B 121.21(17) . . ?
C24B C23B H23B 119.4 . . ?
C19B C24B H24B 120.4 . . ?
C23B C24B C19B 119.24(18) . . ?
C23B C24B H24B 120.4 . . ?

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
O5A H5A N1B 0.93(4) 1.84(4) 2.7541(15) 168(3) 1_455 yes
O5A H5A N2B 0.93(4) 2.52(4) 3.2569(16) 136(3) 1_455 yes
O9A H9A O5A 0.91(3) 1.76(3) 2.6574(14) 169(3) 2_567 yes
N2A H2A O9B 0.86(2) 1.93(2) 2.7724(15) 166(2) . yes
O5B H5B N1A 0.94(3) 1.79(3) 2.7016(15) 163(2) . yes
O9B H9B O5B 0.90(3) 1.79(3) 2.6644(14) 163(2) 2_666 yes
N2B H2B O9A 0.95(3) 1.80(3) 2.7369(15) 169(2) 1_655 yes

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
F1A C15A C16A C17A -179.75(14) . . . . ?
O5A C5A C6A C7A -121.62(13) . . . . ?
O5A C5A C6A C18A 60.18(16) . . . . ?
O5A C5A C9A O9A -4.39(16) . . . . ?
O5A C5A C9A N10A -125.57(11) . . . . ?
O5A C5A C9A C8A 116.85(11) . . . . ?
O8A C8A C9A O9A -52.33(18) . . . . ?
O8A C8A C9A N10A 70.46(17) . . . . ?
O8A C8A C9A C5A -175.97(13) . . . . ?
N1A N2A C3A C4A -0.34(14) . . . . ?
N1A N2A C3A C12A 176.31(11) . . . . ?
N2A N1A C11A N10A 175.54(13) . . . . ?
N2A N1A C11A C4A 0.73(14) . . . . ?
N2A C3A C4A C5A -171.92(17) . . . . ?
N2A C3A C4A C11A 0.74(14) . . . . ?
N2A C3A C12A C13A 24.4(2) . . . . ?
N2A C3A C12A C17A -154.05(13) . . . . ?
N10A C19A C20A C21A 179.22(12) . . . . ?
N10A C19A C24A C23A -178.78(12) . . . . ?
C3A C4A C5A O5A -62.1(2) . . . . ?
C3A C4A C5A C6A 63.8(2) . . . . ?
C3A C4A C5A C9A 174.41(17) . . . . ?
C3A C4A C11A N1A -0.96(15) . . . . ?
C3A C4A C11A N10A -176.73(11) . . . . ?
C3A C12A C13A C14A -178.76(13) . . . . ?
C3A C12A C17A C16A 179.08(14) . . . . ?
C4A C3A C12A C13A -160.05(14) . . . . ?
C4A C3A C12A C17A 21.5(2) . . . . ?
C4A C5A C6A C7A 110.14(14) . . . . ?
C4A C5A C6A C18A -68.06(17) . . . . ?
C4A C5A C9A O9A 119.21(11) . . . . ?
C4A C5A C9A N10A -1.97(12) . . . . ?
C4A C5A C9A C8A -119.55(10) . . . . ?
C5A C4A C11A N1A 174.55(11) . . . . ?
C5A C4A C11A N10A -1.22(15) . . . . ?
C5A C6A C7A C8A 1.94(16) . . . . ?
C6A C5A C9A O9A -123.18(12) . . . . ?
C6A C5A C9A N10A 115.63(11) . . . . ?
C6A C5A C9A C8A -1.94(12) . . . . ?
C6A C7A C8A O8A 175.75(14) . . . . ?
C6A C7A C8A C9A -3.24(16) . . . . ?
C7A C8A C9A O9A 126.70(12) . . . . ?
C7A C8A C9A N10A -110.50(13) . . . . ?
C7A C8A C9A C5A 3.06(13) . . . . ?
C9A N10A C11A N1A -174.93(13) . . . . ?
C9A N10A C11A C4A -0.17(15) . . . . ?
C9A N10A C19A C20A -127.89(13) . . . . ?
C9A N10A C19A C24A 51.60(17) . . . . ?
C9A C5A C6A C7A 0.15(14) . . . . ?
C9A C5A C6A C18A -178.05(12) . . . . ?
C11A N1A N2A C3A -0.22(14) . . . . ?
C11A N10A C9A O9A -123.09(11) . . . . ?
C11A N10A C9A C5A 1.37(13) . . . . ?
C11A N10A C9A C8A 113.22(12) . . . . ?
C11A N10A C19A C20A 19.32(18) . . . . ?
C11A N10A C19A C24A -161.18(12) . . . . ?
C11A C4A C5A O5A 125.42(12) . . . . ?
C11A C4A C5A C6A -108.71(13) . . . . ?
C11A C4A C5A C9A 1.92(13) . . . . ?
C12A C3A C4A C5A 12.0(3) . . . . ?
C12A C3A C4A C11A -175.32(13) . . . . ?
C12A C13A C14A C15A 0.0(2) . . . . ?
C13A C12A C17A C16A 0.6(2) . . . . ?
C13A C14A C15A F1A -179.94(14) . . . . ?
C13A C14A C15A C16A 0.0(2) . . . . ?
C14A C15A C16A C17A 0.3(2) . . . . ?
C15A C16A C17A C12A -0.6(2) . . . . ?
C17A C12A C13A C14A -0.3(2) . . . . ?
C18A C6A C7A C8A 179.99(13) . . . . ?
C19A N10A C9A O9A 28.57(16) . . . . ?
C19A N10A C9A C5A 153.03(11) . . . . ?
C19A N10A C9A C8A -95.12(14) . . . . ?
C19A N10A C11A N1A 33.7(2) . . . . ?
C19A N10A C11A C4A -151.58(12) . . . . ?
C19A C20A C21A C22A -0.5(2) . . . . ?
C20A C19A C24A C23A 0.7(2) . . . . ?
C20A C21A C22A C23A 0.7(2) . . . . ?
C21A C22A C23A C24A -0.3(2) . . . . ?
C22A C23A C24A C19A -0.4(2) . . . . ?
C24A C19A C20A C21A -0.3(2) . . . . ?
F1B C15B C16B C17B 179.06(14) . . . . ?
O5B C5B C6B C7B -120.48(12) . . . . ?
O5B C5B C6B C18B 60.34(15) . . . . ?
O5B C5B C9B O9B -8.87(16) . . . . ?
O5B C5B C9B N10B -129.06(11) . . . . ?
O5B C5B C9B C8B 113.95(11) . . . . ?
O8B C8B C9B O9B -49.81(18) . . . . ?
O8B C8B C9B N10B 73.02(17) . . . . ?
O8B C8B C9B C5B -173.78(13) . . . . ?
N1B N2B C3B C4B -0.39(15) . . . . ?
N1B N2B C3B C12B 175.83(11) . . . . ?
N2B N1B C11B N10B 174.84(14) . . . . ?
N2B N1B C11B C4B 0.02(14) . . . . ?
N2B C3B C4B C5B -171.73(17) . . . . ?
N2B C3B C4B C11B 0.36(14) . . . . ?
N2B C3B C12B C13B 28.8(2) . . . . ?
N2B C3B C12B C17B -147.63(13) . . . . ?
N10B C19B C20B C21B 179.81(13) . . . . ?
N10B C19B C24B C23B 179.90(13) . . . . ?
C3B C4B C5B O5B -61.1(2) . . . . ?
C3B C4B C5B C6B 64.3(2) . . . . ?
C3B C4B C5B C9B 174.77(18) . . . . ?
C3B C4B C11B N1B -0.24(15) . . . . ?
C3B C4B C11B N10B -176.04(11) . . . . ?
C3B C12B C13B C14B -176.28(15) . . . . ?
C3B C12B C17B C16B 175.68(13) . . . . ?
C4B C3B C12B C13B -156.25(15) . . . . ?
C4B C3B C12B C17B 27.3(2) . . . . ?
C4B C5B C6B C7B 110.38(13) . . . . ?
C4B C5B C6B C18B -68.81(16) . . . . ?
C4B C5B C9B O9B 116.32(11) . . . . ?
C4B C5B C9B N10B -3.87(12) . . . . ?
C4B C5B C9B C8B -120.86(10) . . . . ?
C5B C4B C11B N1B 174.97(11) . . . . ?
C5B C4B C11B N10B -0.83(16) . . . . ?
C5B C6B C7B C8B 2.56(16) . . . . ?
C6B C5B C9B O9B -126.18(11) . . . . ?
C6B C5B C9B N10B 113.63(11) . . . . ?
C6B C5B C9B C8B -3.36(12) . . . . ?
C6B C7B C8B O8B 173.75(14) . . . . ?
C6B C7B C8B C9B -4.84(15) . . . . ?
C7B C8B C9B O9B 128.84(12) . . . . ?
C7B C8B C9B N10B -108.33(12) . . . . ?
C7B C8B C9B C5B 4.87(13) . . . . ?
C9B N10B C11B N1B -176.65(13) . . . . ?
C9B N10B C11B C4B -1.89(15) . . . . ?
C9B N10B C19B C20B -124.35(14) . . . . ?
C9B N10B C19B C24B 55.63(18) . . . . ?
C9B C5B C6B C7B 0.72(14) . . . . ?
C9B C5B C6B C18B -178.46(11) . . . . ?
C11B N1B N2B C3B 0.23(14) . . . . ?
C11B N10B C9B O9B -119.97(11) . . . . ?
C11B N10B C9B C5B 3.57(13) . . . . ?
C11B N10B C9B C8B 115.21(12) . . . . ?
C11B N10B C19B C20B 22.22(18) . . . . ?
C11B N10B C19B C24B -157.81(13) . . . . ?
C11B C4B C5B O5B 127.07(12) . . . . ?
C11B C4B C5B C6B -107.58(13) . . . . ?
C11B C4B C5B C9B 2.89(13) . . . . ?
C12B C3B C4B C5B 12.8(3) . . . . ?
C12B C3B C4B C11B -175.12(14) . . . . ?
C12B C13B C14B C15B 0.3(3) . . . . ?
C13B C12B C17B C16B -0.8(2) . . . . ?
C13B C14B C15B F1B -179.65(15) . . . . ?
C13B C14B C15B C16B -0.2(3) . . . . ?
C14B C15B C16B C17B -0.4(3) . . . . ?
C15B C16B C17B C12B 0.9(2) . . . . ?
C17B C12B C13B C14B 0.2(2) . . . . ?
C18B C6B C7B C8B -178.33(13) . . . . ?
C19B N10B C9B O9B 30.87(16) . . . . ?
C19B N10B C9B C5B 154.41(11) . . . . ?
C19B N10B C9B C8B -93.95(14) . . . . ?
C19B N10B C11B N1B 32.6(2) . . . . ?
C19B N10B C11B C4B -152.67(12) . . . . ?
C19B C20B C21B C22B 0.3(2) . . . . ?
C20B C19B C24B C23B -0.1(2) . . . . ?
C20B C21B C22B C23B -0.1(3) . . . . ?
C21B C22B C23B C24B -0.2(3) . . . . ?
C22B C23B C24B C19B 0.3(3) . . . . ?
C24B C19B C20B C21B -0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.510
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6839(8) 29541 23493 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3161(8) 29555 23493 nmt 0.9995 0.0000 0.0000 0.4708 -1.0001 0.0004 -0.0004
-0.0003 -0.9996

_twin_special_details            
;
Component 2 rotated by -179.9844° 
around [0.97 0.23 -0.00] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
####################################################################### 
# 
# 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_780
_database_code_depnum_ccdc_archive 'CCDC 2448542'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-05-04 deposited with the CCDC.	2025-06-24 downloaded from the CCDC.
;
_audit_creation_date             2025-01-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F N3 O4, C2 H6 O S'
_chemical_formula_sum            'C24 H24 F N3 O5 S'
_chemical_formula_weight         485.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H24FN3O5S
_chemical_oxdiff_usercomment     780
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.4253(3)
_cell_length_b                   10.7006(3)
_cell_length_c                   11.1367(3)
_cell_angle_alpha                95.717(2)
_cell_angle_beta                 91.608(2)
_cell_angle_gamma                110.539(3)
_cell_volume                     1154.97(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16770
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.3630
_cell_measurement_theta_min      3.9700
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.418
_exptl_absorpt_coefficient_mu    1.676
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.349
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 1 0.1268
0 1 -1 0.1124
-1 1 0 0.0843
1 -1 0 0.1270
1 0 0 0.0304
-1 0 0 0.0210
0 -1 0 0.1454

_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0014 -1.0005 1.0001 -0.0031 -0.1847 0.0653
0.0014 1.0005 -1.0001 0.0031 0.1847 -0.0653
-0.9996 1.0010 -0.0004 -0.1308 0.1020 0.0639
0.9996 -1.0010 0.0004 0.1308 -0.1020 -0.0639
1.0006 -0.0009 0.0004 0.1539 0.0368 0.0008
-1.0006 0.0009 -0.0004 -0.1539 -0.0368 -0.0008
-0.0010 -1.0001 -0.0000 -0.0231 -0.1388 -0.0647

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.018
_diffrn_reflns_theta_min         3.998
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -32.00   0.50    0.25    --  -46.47 -27.00  30.00  178
  2  ω     32.00 121.00   0.50    0.25    --   46.47  27.00-167.00  178
  3  ω     32.00 121.00   0.50    0.25    --   46.47  27.00-167.00  178
  4  ω    -28.00  33.00   0.50    0.25    --   46.47 -27.00  30.00  122
  5  ω   -167.00 -77.00   0.50    1.00    --  -91.75 -27.00  30.00  180
  6  ω     99.00 178.00   0.50    1.00    --  113.25  27.00-167.00  158
  7  ω    -33.00  29.00   0.50    0.25    --  -46.47  27.00-167.00  124
  8  ω    -29.00  27.00   0.50    0.25    --   46.47 -19.00-120.00  112
  9  ω     34.00  93.00   0.50    0.25    --   46.47-125.00  60.00  118
 10  ω    -29.00  27.00   0.50    0.25    --   46.47 -19.00 -60.00  112
 11  ω    -25.00  63.00   0.50    0.25    --   46.47 -57.00-180.00  176
 12  ω    -71.00 -19.00   0.50    1.00    --  -91.75  61.00-180.00  104
 13  ω    -85.00 -22.00   0.50    1.00    --  -91.75 125.00-120.00  126
 14  ω    -51.00 -19.00   0.50    1.00    --  -91.75  45.00   0.00   64
 15  ω    -51.00 -19.00   0.50    1.00    --  -91.75  45.00-180.00   64
 16  ω     43.00 111.00   0.50    1.00    --  113.25-125.00   0.00  136
 17  ω     96.00 178.00   0.50    1.00    --  113.25  15.00 -30.00  164
 18  ω     41.00 106.00   0.50    1.00    --  113.25 -95.00  60.00  130
 19  ω     96.00 178.00   0.50    1.00    --  113.25  15.00-120.00  164
 20  ω     95.00 178.00   0.50    1.00    --  113.25 125.00 150.00  166
 21  ω     96.00 178.00   0.50    1.00    --  113.25  15.00 120.00  164
 22  ω     41.00 106.00   0.50    1.00    --  113.25 -95.00 120.00  130
 23  ω    121.00 171.00   0.50    1.00    --  113.25  30.00  60.00  100
 24  ω     71.00 101.00   0.50    1.00    --  113.25 -95.00-150.00   60
 25  ω     43.00  69.00   0.50    1.00    --  113.25 -95.00-150.00   52
 26  ω     41.00  68.00   0.50    1.00    --  113.25 -61.00 -30.00   54
 27  ω     99.00 132.00   0.50    1.00    --  113.25  30.00  30.00   66
 28  ω     78.00 106.00   0.50    1.00    --  113.25 -95.00   0.00   56
 29  ω     78.00 111.00   0.50    1.00    --  113.25-125.00 -30.00   66
 30  ω    116.00 142.00   0.50    1.00    --  113.25  15.00 150.00   52
 31  ω    102.00 178.00   0.50    1.00    --  113.25  77.00 -30.00  152
 32  ω     43.00  75.00   0.50    1.00    --  113.25-125.00  30.00   64
 33  ω     79.00 111.00   0.50    1.00    --  113.25-125.00  30.00   64
 34  ω     95.00 173.00   0.50    1.00    --  113.25 125.00   0.00  156
 35  ω     81.00 106.00   0.50    1.00    --  113.25 -95.00-120.00   50
 36  ω     95.00 141.00   0.50    1.00    --  113.25 125.00  30.00   92
 37  ω     76.00 111.00   0.50    1.00    --  113.25-125.00  60.00   70
 38  ω     43.00  69.00   0.50    1.00    --  113.25 -61.00 120.00   52
 39  ω     41.00  95.00   0.50    1.00    --  113.25 -77.00 -60.00  108
 40  ω     84.00 111.00   0.50    1.00    --  113.25-125.00 -90.00   54
 41  ω     42.00  67.00   0.50    1.00    --  113.25 -61.00 -90.00   50
 42  ω     64.00 111.00   0.50    1.00    --  113.25-125.00 -60.00   94
 43  ω     85.00 111.00   0.50    1.00    --  113.25-125.00 150.00   52
 44  ω     96.00 157.00   0.50    1.00    --  113.25 125.00  90.00  122
 45  ω     55.00  80.00   0.50    1.00    --  113.25-125.00 -90.00   50
 46  ω     43.00  69.00   0.50    1.00    --  113.25 -61.00 150.00   52
 47  ω     42.00  67.00   0.50    1.00    --  113.25 -82.00  15.63   50
 48  ω     96.00 123.00   0.50    1.00    --  113.25 -82.00  15.63   54
 49  ω     75.00 101.00   0.50    1.00    --  113.25 -95.00 150.00   52
 50  ω    147.00 172.00   0.50    1.00    --  113.25  30.00  30.00   50
 51  ω     72.00 101.00   0.50    1.00    --  113.25 -95.00-180.00   58
 52  ω     48.00  81.00   0.50    1.00    --  113.25-125.00-150.00   66
 53  ω     86.00 111.00   0.50    1.00    --  113.25-125.00-150.00   50
 54  ω     49.00  75.00   0.50    1.00    --  113.25 -82.00-132.84   52
 55  ω     81.00 107.00   0.50    1.00    --  113.25 -82.00-132.84   52
 56  ω    144.00 178.00   0.50    1.00    --  113.25  30.00-180.00   68
 57  ω     41.00  74.00   0.50    1.00    --  113.25 -95.00 150.00   66
 58  ω     46.00  74.00   0.50    1.00    --  113.25 -77.00  90.00   56
 59  ω    105.00 163.00   0.50    1.00    --  113.25  45.00 150.00  116
 60  ω    131.00 177.00   0.50    1.00    --  113.25  45.00-120.00   92
 61  ω     48.00  79.00   0.50    1.00    --  113.25 -81.00-156.77   62
 62  ω     84.00 110.00   0.50    1.00    --  113.25 -81.00-156.77   52
 63  ω    138.00 178.00   0.50    1.00    --  113.25  45.00 120.00   80
 64  ω     45.00  71.00   0.50    1.00    --  113.25 -77.00 -90.00   52
 65  ω     82.00 108.00   0.50    1.00    --  113.25-125.00  90.00   52
 66  ω     85.00 111.00   0.50    1.00    --  113.25-125.00-180.00   52
 67  ω     63.00 111.00   0.50    1.00    --  113.25-125.00 120.00   96
 68  ω    110.00 136.00   0.50    1.00    --  113.25  45.00 -30.00   52
 69  ω     42.00  69.00   0.50    1.00    --  113.25 -61.00  60.00   54
 70  ω     41.00  71.00   0.50    1.00    --  113.25 -61.00  30.00   60
 71  ω    115.00 141.00   0.50    1.00    --  113.25  61.00 -90.00   52
 72  ω    103.00 129.00   0.50    1.00    --  113.25  61.00  30.00   52
 73  ω     97.00 124.00   0.50    1.00    --  113.25  61.00 120.00   54
 74  ω    135.00 175.00   0.50    1.00    --  113.25  15.00 -60.00   80
 75  ω    101.00 162.00   0.50    1.00    --  113.25 125.00-180.00  122
 76  ω    101.00 140.00   0.50    1.00    --  113.25  77.00-120.00   78
 77  ω     83.00 109.00   0.50    1.00    --  113.25 -82.00 -88.85   52
 78  ω     43.00  71.00   0.50    1.00    --  113.25-125.00  60.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1537846000
_diffrn_orient_matrix_UB_12      0.0229305000
_diffrn_orient_matrix_UB_13      0.0200144000
_diffrn_orient_matrix_UB_21      0.0369521000
_diffrn_orient_matrix_UB_22      0.1387475000
_diffrn_orient_matrix_UB_23      -0.0457953000
_diffrn_orient_matrix_UB_31      0.0008047000
_diffrn_orient_matrix_UB_32      0.0647132000
_diffrn_orient_matrix_UB_33      0.1300713000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4711
_reflns_number_total             4966
_reflns_odcompleteness_completeness 97.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.5190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0975
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22),
 C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C13(H13A,H13B,H13C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
S27 S 0.29317(3) 0.81298(3) 0.75328(3) 0.02123(10) Uani 1 1 d . . . . .
O27 O 0.40541(11) 0.76389(10) 0.70901(9) 0.0270(2) Uani 1 1 d . . . . .
C28 C 0.27468(16) 0.91739(16) 0.64345(13) 0.0284(3) Uani 1 1 d . . . . .
H28A H 0.363273 0.988692 0.637031 0.043 Uiso 1 1 calc R U . . .
H28B H 0.206998 0.957646 0.668298 0.043 Uiso 1 1 calc R U . . .
H28C H 0.243618 0.863118 0.564790 0.043 Uiso 1 1 calc R U . . .
C29 C 0.37413(16) 0.94007(15) 0.87507(13) 0.0283(3) Uani 1 1 d . . . . .
H29A H 0.396395 0.898859 0.943639 0.042 Uiso 1 1 calc R U . . .
H29B H 0.311945 0.987163 0.899544 0.042 Uiso 1 1 calc R U . . .
H29C H 0.458662 1.004194 0.849125 0.042 Uiso 1 1 calc R U . . .
F17 F 1.08147(10) 0.03171(12) 0.83886(10) 0.0434(3) Uani 1 1 d . . . . .
O7 O 0.38285(10) 0.25495(9) 0.91306(8) 0.01971(19) Uani 1 1 d . . . . .
O9 O 0.41524(12) 0.52624(10) 0.73580(9) 0.0260(2) Uani 1 1 d . . . . .
H9 H 0.399(2) 0.599(3) 0.749(2) 0.054(7) Uiso 1 1 d . . . . .
O10 O 0.32142(11) 0.61149(10) 0.94598(9) 0.0249(2) Uani 1 1 d . . . . .
O26 O -0.01197(11) 0.38589(11) 0.38817(10) 0.0317(2) Uani 1 1 d . . . . .
N1 N 0.61575(12) 0.21397(12) 0.60414(10) 0.0234(2) Uani 1 1 d . . . . .
N2 N 0.51840(13) 0.23416(12) 0.53239(10) 0.0231(2) Uani 1 1 d . . . . .
H2 H 0.527(2) 0.227(2) 0.4535(19) 0.034(5) Uiso 1 1 d . . . . .
N6 N 0.66120(12) 0.23421(12) 0.81698(11) 0.0228(2) Uani 1 1 d . . . . .
H6 H 0.6588(19) 0.283(2) 0.8818(19) 0.030(5) Uiso 1 1 d . . . . .
C3 C 0.42873(14) 0.27451(13) 0.59499(12) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.46660(14) 0.28047(13) 0.71706(12) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.58421(14) 0.24135(13) 0.71639(12) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.40793(13) 0.33269(13) 0.81926(11) 0.0183(2) Uani 1 1 d . . . . .
C9 C 0.38397(13) 0.45031(13) 0.82719(11) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.33410(13) 0.49868(13) 0.93619(11) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.30858(14) 0.41117(13) 1.02893(11) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.272877 0.435168 1.101625 0.025 Uiso 1 1 calc R U . . .
C12 C 0.33401(13) 0.29506(13) 1.01572(11) 0.0199(3) Uani 1 1 d . . . . .
C13 C 0.31347(16) 0.19849(14) 1.10655(12) 0.0258(3) Uani 1 1 d . . . . .
H13A H 0.250127 0.109922 1.071315 0.039 Uiso 1 1 calc R U . . .
H13B H 0.274865 0.229739 1.177651 0.039 Uiso 1 1 calc R U . . .
H13C H 0.401848 0.192018 1.130661 0.039 Uiso 1 1 calc R U . . .
C14 C 0.76820(14) 0.18327(14) 0.81622(12) 0.0214(3) Uani 1 1 d . . . . .
C15 C 0.78039(15) 0.08970(14) 0.72389(12) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.715843 0.060371 0.655775 0.029 Uiso 1 1 calc R U . . .
C16 C 0.88649(16) 0.03948(15) 0.73141(13) 0.0280(3) Uani 1 1 d . . . . .
H16 H 0.895890 -0.022740 0.668354 0.034 Uiso 1 1 calc R U . . .
C17 C 0.97724(15) 0.08154(16) 0.83162(15) 0.0298(3) Uani 1 1 d . . . . .
C18 C 0.96750(15) 0.17167(17) 0.92457(15) 0.0316(3) Uani 1 1 d . . . . .
H18 H 1.031389 0.198228 0.993113 0.038 Uiso 1 1 calc R U . . .
C19 C 0.86297(15) 0.22341(15) 0.91696(13) 0.0266(3) Uani 1 1 d . . . . .
H19 H 0.855685 0.286360 0.980386 0.032 Uiso 1 1 calc R U . . .
C20 C 0.31446(14) 0.30071(13) 0.53615(12) 0.0210(3) Uani 1 1 d . . . . .
C21 C 0.18207(15) 0.25027(14) 0.57701(12) 0.0242(3) Uani 1 1 d . . . . .
H21 H 0.165552 0.195693 0.641277 0.029 Uiso 1 1 calc R U . . .
C22 C 0.07551(15) 0.27894(15) 0.52501(13) 0.0268(3) Uani 1 1 d . . . . .
H22 H -0.013987 0.243208 0.552869 0.032 Uiso 1 1 calc R U . . .
C23 C 0.09899(15) 0.36068(14) 0.43118(13) 0.0245(3) Uani 1 1 d . . . . .
C24 C 0.22986(15) 0.41050(14) 0.38913(12) 0.0245(3) Uani 1 1 d . . . . .
H24 H 0.246459 0.465500 0.325179 0.029 Uiso 1 1 calc R U . . .
C25 C 0.33600(15) 0.37946(14) 0.44105(12) 0.0228(3) Uani 1 1 d . . . . .
H25 H 0.424747 0.412485 0.411212 0.027 Uiso 1 1 calc R U . . .
C26 C 0.01044(18) 0.47573(17) 0.29780(16) 0.0368(4) Uani 1 1 d . . . . .
H26A H 0.038441 0.436140 0.224616 0.055 Uiso 1 1 calc R U . . .
H26B H 0.082856 0.561265 0.328019 0.055 Uiso 1 1 calc R U . . .
H26C H -0.074606 0.491444 0.278769 0.055 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
S27 O27 1.5166(10) . ?
S27 C28 1.7865(15) . ?
S27 C29 1.7788(15) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
F17 C17 1.3718(16) . ?
O7 C8 1.3738(15) . ?
O7 C12 1.3561(15) . ?
O9 H9 0.85(3) . ?
O9 C9 1.3416(16) . ?
O10 C10 1.2543(16) . ?
O26 C23 1.3617(17) . ?
O26 C26 1.4283(19) . ?
N1 N2 1.3630(16) . ?
N1 C5 1.3321(17) . ?
N2 H2 0.88(2) . ?
N2 C3 1.3441(17) . ?
N6 H6 0.85(2) . ?
N6 C5 1.3836(17) . ?
N6 C14 1.4029(17) . ?
C3 C4 1.3939(18) . ?
C3 C20 1.4677(18) . ?
C4 C5 1.4279(18) . ?
C4 C8 1.4607(17) . ?
C8 C9 1.3616(18) . ?
C9 C10 1.4528(17) . ?
C10 C11 1.4309(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3537(19) . ?
C12 C13 1.4839(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.4026(19) . ?
C14 C19 1.401(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3929(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.373(2) . ?
C17 C18 1.374(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.402(2) . ?
C20 C25 1.3931(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.401(2) . ?
C23 C24 1.393(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
O27 S27 C28 104.44(6) . . ?
O27 S27 C29 104.89(7) . . ?
C29 S27 C28 98.87(7) . . ?
S27 C28 H28A 109.5 . . ?
S27 C28 H28B 109.5 . . ?
S27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
S27 C29 H29A 109.5 . . ?
S27 C29 H29B 109.5 . . ?
S27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C12 O7 C8 120.11(10) . . ?
C9 O9 H9 112.9(16) . . ?
C23 O26 C26 116.99(12) . . ?
C5 N1 N2 104.29(11) . . ?
N1 N2 H2 117.4(13) . . ?
C3 N2 N1 113.40(11) . . ?
C3 N2 H2 128.9(13) . . ?
C5 N6 H6 116.9(13) . . ?
C5 N6 C14 125.85(12) . . ?
C14 N6 H6 115.2(13) . . ?
N2 C3 C4 106.51(12) . . ?
N2 C3 C20 122.68(12) . . ?
C4 C3 C20 130.79(12) . . ?
C3 C4 C5 104.19(11) . . ?
C3 C4 C8 126.30(12) . . ?
C5 C4 C8 129.05(12) . . ?
N1 C5 N6 122.19(12) . . ?
N1 C5 C4 111.60(12) . . ?
N6 C5 C4 126.20(12) . . ?
O7 C8 C4 114.09(11) . . ?
C9 C8 O7 120.97(11) . . ?
C9 C8 C4 124.88(12) . . ?
O9 C9 C8 119.20(12) . . ?
O9 C9 C10 119.75(11) . . ?
C8 C9 C10 120.92(12) . . ?
O10 C10 C9 120.49(12) . . ?
O10 C10 C11 124.74(12) . . ?
C11 C10 C9 114.71(11) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.68(12) . . ?
C12 C11 H11 119.2 . . ?
O7 C12 C13 112.36(11) . . ?
C11 C12 O7 121.57(12) . . ?
C11 C12 C13 126.07(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N6 123.57(13) . . ?
C19 C14 N6 117.44(12) . . ?
C19 C14 C15 118.90(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.45(14) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.79(14) . . ?
C17 C16 H16 120.6 . . ?
F17 C17 C16 118.65(14) . . ?
F17 C17 C18 118.93(14) . . ?
C16 C17 C18 122.42(14) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.09(14) . . ?
C19 C18 H18 120.5 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.35(14) . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C3 120.58(12) . . ?
C25 C20 C3 120.78(12) . . ?
C25 C20 C21 118.61(13) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.77(13) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.13(13) . . ?
C23 C22 H22 119.9 . . ?
O26 C23 C22 115.60(13) . . ?
O26 C23 C24 124.77(13) . . ?
C24 C23 C22 119.63(13) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.75(13) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.09(13) . . ?
C24 C25 H25 119.5 . . ?
O26 C26 H26A 109.5 . . ?
O26 C26 H26B 109.5 . . ?
O26 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C28 H28B F17 0.98 2.55 3.4255(18) 148.3 1_465 yes
O9 H9 O27 0.85(3) 1.85(3) 2.6265(14) 152(2) . yes
N2 H2 O27 0.88(2) 1.96(2) 2.8246(15) 165.3(19) 2_666 yes
N6 H6 O10 0.85(2) 2.09(2) 2.9364(15) 169.6(18) 2_667 yes
C13 H13C O27 0.98 2.53 3.4117(18) 149.2 2_667 yes
C15 H15 N1 0.95 2.34 2.8844(18) 115.8 . yes
C19 H19 O10 0.95 2.57 3.3401(17) 138.5 2_667 yes

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
F17 C17 C18 C19 179.33(14) . . . . ?
O7 C8 C9 O9 177.18(11) . . . . ?
O7 C8 C9 C10 1.4(2) . . . . ?
O9 C9 C10 O10 -0.7(2) . . . . ?
O9 C9 C10 C11 -177.99(12) . . . . ?
O10 C10 C11 C12 -175.02(13) . . . . ?
O26 C23 C24 C25 179.15(13) . . . . ?
N1 N2 C3 C4 -0.78(16) . . . . ?
N1 N2 C3 C20 -179.29(12) . . . . ?
N2 N1 C5 N6 -179.12(12) . . . . ?
N2 N1 C5 C4 -0.48(15) . . . . ?
N2 C3 C4 C5 0.42(14) . . . . ?
N2 C3 C4 C8 173.18(12) . . . . ?
N2 C3 C20 C21 133.86(14) . . . . ?
N2 C3 C20 C25 -48.09(19) . . . . ?
N6 C14 C15 C16 -177.48(13) . . . . ?
N6 C14 C19 C18 176.90(13) . . . . ?
C3 C4 C5 N1 0.05(15) . . . . ?
C3 C4 C5 N6 178.61(13) . . . . ?
C3 C4 C8 O7 136.77(13) . . . . ?
C3 C4 C8 C9 -46.0(2) . . . . ?
C3 C20 C21 C22 177.49(13) . . . . ?
C3 C20 C25 C24 -176.59(12) . . . . ?
C4 C3 C20 C21 -44.2(2) . . . . ?
C4 C3 C20 C25 133.80(15) . . . . ?
C4 C8 C9 O9 0.1(2) . . . . ?
C4 C8 C9 C10 -175.67(12) . . . . ?
C5 N1 N2 C3 0.79(15) . . . . ?
C5 N6 C14 C15 -24.4(2) . . . . ?
C5 N6 C14 C19 159.17(13) . . . . ?
C5 C4 C8 O7 -52.29(18) . . . . ?
C5 C4 C8 C9 124.97(16) . . . . ?
C8 O7 C12 C11 0.08(19) . . . . ?
C8 O7 C12 C13 -179.96(11) . . . . ?
C8 C4 C5 N1 -172.43(13) . . . . ?
C8 C4 C5 N6 6.1(2) . . . . ?
C8 C9 C10 O10 175.01(13) . . . . ?
C8 C9 C10 C11 -2.24(19) . . . . ?
C9 C10 C11 C12 2.09(19) . . . . ?
C10 C11 C12 O7 -1.1(2) . . . . ?
C10 C11 C12 C13 178.96(13) . . . . ?
C12 O7 C8 C4 177.12(11) . . . . ?
C12 O7 C8 C9 -0.26(18) . . . . ?
C14 N6 C5 N1 -8.2(2) . . . . ?
C14 N6 C5 C4 173.34(13) . . . . ?
C14 C15 C16 C17 1.1(2) . . . . ?
C15 C14 C19 C18 0.3(2) . . . . ?
C15 C16 C17 F17 179.88(13) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
C19 C14 C15 C16 -1.1(2) . . . . ?
C20 C3 C4 C5 178.76(13) . . . . ?
C20 C3 C4 C8 -8.5(2) . . . . ?
C20 C21 C22 C23 -0.8(2) . . . . ?
C21 C20 C25 C24 1.5(2) . . . . ?
C21 C22 C23 O26 -178.31(13) . . . . ?
C21 C22 C23 C24 1.3(2) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C20 -1.0(2) . . . . ?
C25 C20 C21 C22 -0.6(2) . . . . ?
C26 O26 C23 C22 176.15(14) . . . . ?
C26 O26 C23 C24 -3.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.863
