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

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

data_ketfa_0m
_database_code_depnum_ccdc_archive 'CCDC 2372345'
loop_
_audit_author_name
_audit_author_address
'SMRUTI REKHA ROUT'
;INSTITUTION OF CHEMICAL TECHNOLOGY
India
;
_audit_update_record             
;
2024-07-21 deposited with the CCDC.	2024-10-16 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         'C22 H23 F N3 O3,C4 H3 O4'
_chemical_formula_sum            'C26 H26 F N3 O7'
_chemical_formula_weight         511.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.662(2)
_cell_length_b                   21.965(1)
_cell_length_c                   16.468(1)
_cell_angle_alpha                90
_cell_angle_beta                 91.69(1)
_cell_angle_gamma                90
_cell_volume                     2408.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3809
_cell_measurement_theta_min      0.974
_cell_measurement_theta_max      0.979

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.979
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49293
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5537
_reflns_number_gt                3809
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0409P)²+1.1124P] 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         5516
_refine_ls_number_parameters     339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
F F 1.0221(2) 0.67205(6) 0.48194(9) 0.0694(4) Uani 1 1 d . . . . .
O7 O 0.4188(2) 0.25940(7) 0.38666(9) 0.0461(4) Uani 1 1 d . . . . .
O1 O 0.7786(2) 0.11646(7) 0.26264(11) 0.0543(4) Uani 1 1 d . . . . .
O6 O 0.6961(2) 0.21541(8) 0.43406(10) 0.0594(5) Uani 1 1 d . . . . .
O2 O 0.2109(2) 0.22365(7) 0.19990(11) 0.0592(5) Uani 1 1 d . . . . .
O5 O -0.1218(2) 0.15229(9) 0.54448(11) 0.0653(5) Uani 1 1 d . . . . .
H5 H -0.156318 0.174341 0.506383 0.098 Uiso 1 1 calc R U . . .
N3 N 0.6579(2) 0.30437(7) 0.27322(10) 0.0336(4) Uani 1 1 d . . . . .
H3 H 0.574761 0.285494 0.314389 0.040 Uiso 1 1 calc R U . . .
N2 N 0.4983(2) 0.17131(7) 0.23388(10) 0.0364(4) Uani 1 1 d . . . . .
O4 O 0.1565(3) 0.11784(9) 0.60116(11) 0.0724(6) Uani 1 1 d . . . . .
N1 N 0.1886(3) 0.14181(8) 0.28280(12) 0.0469(5) Uani 1 1 d . . . . .
O3 O 0.3413(2) 0.48983(7) 0.37151(11) 0.0642(5) Uani 1 1 d . . . . .
C24 C 0.5096(3) 0.22333(9) 0.43370(12) 0.0363(4) Uani 1 1 d . . . . .
C10 C 0.7370(3) 0.39161(9) 0.36570(13) 0.0410(5) Uani 1 1 d . . . . .
H10A H 0.846595 0.414867 0.390346 0.049 Uiso 1 1 calc R U . . .
H10B H 0.657790 0.375013 0.408944 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8211(3) 0.34013(9) 0.31617(13) 0.0409(5) Uani 1 1 d . . . . .
H9A H 0.910849 0.356655 0.276410 0.049 Uiso 1 1 calc R U . . .
H9B H 0.898580 0.313191 0.351698 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5260(3) 0.34481(9) 0.22132(12) 0.0391(5) Uani 1 1 d . . . . .
H13A H 0.417652 0.321011 0.196757 0.047 Uiso 1 1 calc R U . . .
H13B H 0.603617 0.362095 0.178046 0.047 Uiso 1 1 calc R U . . .
C11 C 0.6052(3) 0.43375(8) 0.31220(12) 0.0370(4) Uani 1 1 d . . . . .
H11 H 0.688482 0.450426 0.269468 0.044 Uiso 1 1 calc R U . . .
C1 C 0.2713(3) 0.09217(9) 0.32276(13) 0.0409(5) Uani 1 1 d . . . . .
C22 C 0.1912(3) 0.18891(9) 0.49406(12) 0.0397(5) Uani 1 1 d . . . . .
H22 H 0.121117 0.215333 0.459392 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4395(3) 0.39556(9) 0.27181(13) 0.0405(5) Uani 1 1 d . . . . .
H12A H 0.356166 0.378209 0.313220 0.049 Uiso 1 1 calc R U . . .
H12B H 0.355404 0.421415 0.237300 0.049 Uiso 1 1 calc R U . . .
C27 C 0.2907(3) 0.18179(9) 0.23686(13) 0.0425(5) Uani 1 1 d . . . . .
C5 C 0.4756(3) 0.08138(9) 0.31793(12) 0.0380(4) Uani 1 1 d . . . . .
C23 C 0.3877(3) 0.18698(9) 0.49119(12) 0.0388(4) Uani 1 1 d . . . . .
H23 H 0.455849 0.161258 0.527382 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6600(3) 0.53456(9) 0.39236(12) 0.0383(4) Uani 1 1 d . . . . .
C6 C 0.5976(3) 0.12280(9) 0.27122(13) 0.0380(4) Uani 1 1 d . . . . .
C16 C 0.8610(3) 0.53803(9) 0.37272(13) 0.0438(5) Uani 1 1 d . . . . .
H16 H 0.914367 0.508917 0.338496 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7552(3) 0.25467(9) 0.22623(14) 0.0434(5) Uani 1 1 d . . . . .
H8A H 0.839527 0.231072 0.263529 0.052 Uiso 1 1 calc R U . . .
H8B H 0.842350 0.273235 0.187077 0.052 Uiso 1 1 calc R U . . .
C7 C 0.6140(3) 0.21140(9) 0.18126(13) 0.0433(5) Uani 1 1 d . . . . .
H7A H 0.520853 0.235108 0.147738 0.052 Uiso 1 1 calc R U . . .
H7B H 0.691858 0.186336 0.145292 0.052 Uiso 1 1 calc R U . . .
C21 C 0.0764(3) 0.15045(10) 0.55062(13) 0.0459(5) Uani 1 1 d . . . . .
C14 C 0.5205(3) 0.48664(9) 0.35967(13) 0.0403(5) Uani 1 1 d . . . . .
C20 C 0.5845(3) 0.57867(10) 0.44432(13) 0.0466(5) Uani 1 1 d . . . . .
H20 H 0.450707 0.576768 0.458670 0.056 Uiso 1 1 calc R U . . .
C17 C 0.9832(3) 0.58416(10) 0.40329(14) 0.0506(5) Uani 1 1 d . . . . .
H17 H 1.117902 0.586196 0.390181 0.061 Uiso 1 1 calc R U . . .
C19 C 0.7049(4) 0.62517(10) 0.47492(14) 0.0511(6) Uani 1 1 d . . . . .
H19 H 0.653811 0.654593 0.509270 0.061 Uiso 1 1 calc R U . . .
C26 C 0.5595(3) 0.03053(10) 0.35691(14) 0.0485(5) Uani 1 1 d . . . . .
H26 H 0.696495 0.023130 0.353840 0.058 Uiso 1 1 calc R U . . .
C18 C 0.9015(3) 0.62650(9) 0.45301(13) 0.0469(5) Uani 1 1 d . . . . .
C4 C 0.4420(4) -0.00854(10) 0.39961(15) 0.0551(6) Uani 1 1 d . . . . .
H4 H 0.498593 -0.042440 0.425215 0.066 Uiso 1 1 calc R U . . .
C2 C 0.1527(3) 0.05262(11) 0.36704(15) 0.0567(6) Uani 1 1 d . . . . .
H2 H 0.015997 0.060096 0.371164 0.068 Uiso 1 1 calc R U . . .
C3 C 0.2372(4) 0.00292(11) 0.40436(16) 0.0594(6) Uani 1 1 d . . . . .
H3A H 0.156987 -0.023550 0.433260 0.071 Uiso 1 1 calc R U . . .
H1 H 0.050(4) 0.1456(12) 0.2794(16) 0.074(8) 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
F C18 1.360(2) . ?
O7 C24 1.251(2) . ?
O1 C6 1.226(2) . ?
O6 C24 1.255(2) . ?
O2 C27 1.216(2) . ?
O5 C21 1.322(2) . ?
O5 H5 0.8200 . ?
N3 C8 1.497(2) . ?
N3 C13 1.499(2) . ?
N3 C9 1.502(2) . ?
N3 H3 0.9800 . ?
N2 C6 1.388(2) . ?
N2 C27 1.404(2) . ?
N2 C7 1.470(3) . ?
O4 C21 1.210(2) . ?
N1 C27 1.355(3) . ?
N1 C1 1.380(3) . ?
N1 H1 0.92(3) . ?
O3 C14 1.217(2) . ?
C24 C23 1.496(3) . ?
C10 C9 1.512(3) . ?
C10 C11 1.536(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C13 C12 1.515(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 C14 1.518(3) . ?
C11 C12 1.523(3) . ?
C11 H11 0.9800 . ?
C1 C5 1.386(3) . ?
C1 C2 1.395(3) . ?
C22 C23 1.312(3) . ?
C22 C21 1.486(3) . ?
C22 H22 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 C26 1.397(3) . ?
C5 C6 1.455(3) . ?
C23 H23 0.9300 . ?
C15 C16 1.389(3) . ?
C15 C20 1.396(3) . ?
C15 C14 1.494(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C8 C7 1.515(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C20 C19 1.384(3) . ?
C20 H20 0.9300 . ?
C17 C18 1.363(3) . ?
C17 H17 0.9300 . ?
C19 C18 1.369(3) . ?
C19 H19 0.9300 . ?
C26 C4 1.370(3) . ?
C26 H26 0.9300 . ?
C4 C3 1.392(3) . ?
C4 H4 0.9300 . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O5 H5 109.5 . . ?
C8 N3 C13 113.14(16) . . ?
C8 N3 C9 107.83(14) . . ?
C13 N3 C9 111.26(14) . . ?
C8 N3 H3 108.2 . . ?
C13 N3 H3 108.2 . . ?
C9 N3 H3 108.2 . . ?
C6 N2 C27 124.55(17) . . ?
C6 N2 C7 118.02(16) . . ?
C27 N2 C7 117.18(17) . . ?
C27 N1 C1 125.30(18) . . ?
C27 N1 H1 115.1(17) . . ?
C1 N1 H1 118.9(17) . . ?
O7 C24 O6 123.45(18) . . ?
O7 C24 C23 117.91(17) . . ?
O6 C24 C23 118.63(17) . . ?
C9 C10 C11 110.86(17) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N3 C9 C10 111.76(15) . . ?
N3 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N3 C13 C12 110.44(16) . . ?
N3 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
N3 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C14 C11 C12 111.76(16) . . ?
C14 C11 C10 112.38(16) . . ?
C12 C11 C10 108.25(15) . . ?
C14 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
C10 C11 H11 108.1 . . ?
N1 C1 C5 119.13(18) . . ?
N1 C1 C2 121.13(19) . . ?
C5 C1 C2 119.7(2) . . ?
C23 C22 C21 122.45(18) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C13 C12 C11 111.25(16) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O2 C27 N1 123.35(19) . . ?
O2 C27 N2 121.5(2) . . ?
N1 C27 N2 115.13(18) . . ?
C1 C5 C26 119.39(19) . . ?
C1 C5 C6 119.23(18) . . ?
C26 C5 C6 121.37(18) . . ?
C22 C23 C24 124.50(18) . . ?
C22 C23 H23 117.8 . . ?
C24 C23 H23 117.8 . . ?
C16 C15 C20 118.15(19) . . ?
C16 C15 C14 123.26(18) . . ?
C20 C15 C14 118.58(19) . . ?
O1 C6 N2 119.57(18) . . ?
O1 C6 C5 123.82(18) . . ?
N2 C6 C5 116.61(16) . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
N3 C8 C7 115.97(16) . . ?
N3 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
N3 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
N2 C7 C8 114.62(18) . . ?
N2 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O4 C21 O5 119.34(19) . . ?
O4 C21 C22 122.90(19) . . ?
O5 C21 C22 117.76(18) . . ?
O3 C14 C15 120.29(18) . . ?
O3 C14 C11 120.50(19) . . ?
C15 C14 C11 119.21(17) . . ?
C19 C20 C15 121.3(2) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C18 C17 C16 118.5(2) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C18 C19 C20 117.9(2) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C4 C26 C5 120.7(2) . . ?
C4 C26 H26 119.7 . . ?
C5 C26 H26 119.7 . . ?
F C18 C17 118.0(2) . . ?
F C18 C19 118.9(2) . . ?
C17 C18 C19 123.1(2) . . ?
C26 C4 C3 119.4(2) . . ?
C26 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?

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
C8 N3 C9 C10 -179.89(17) . . . . ?
C13 N3 C9 C10 55.5(2) . . . . ?
C11 C10 C9 N3 -56.3(2) . . . . ?
C8 N3 C13 C12 -177.59(16) . . . . ?
C9 N3 C13 C12 -56.0(2) . . . . ?
C9 C10 C11 C14 -179.12(17) . . . . ?
C9 C10 C11 C12 57.0(2) . . . . ?
C27 N1 C1 C5 1.1(3) . . . . ?
C27 N1 C1 C2 -178.4(2) . . . . ?
N3 C13 C12 C11 58.7(2) . . . . ?
C14 C11 C12 C13 177.22(16) . . . . ?
C10 C11 C12 C13 -58.5(2) . . . . ?
C1 N1 C27 O2 176.9(2) . . . . ?
C1 N1 C27 N2 -2.4(3) . . . . ?
C6 N2 C27 O2 -176.71(19) . . . . ?
C7 N2 C27 O2 -2.7(3) . . . . ?
C6 N2 C27 N1 2.7(3) . . . . ?
C7 N2 C27 N1 176.72(17) . . . . ?
N1 C1 C5 C26 -178.74(19) . . . . ?
C2 C1 C5 C26 0.7(3) . . . . ?
N1 C1 C5 C6 0.3(3) . . . . ?
C2 C1 C5 C6 179.7(2) . . . . ?
C21 C22 C23 C24 178.06(19) . . . . ?
O7 C24 C23 C22 2.2(3) . . . . ?
O6 C24 C23 C22 -176.6(2) . . . . ?
C27 N2 C6 O1 177.45(19) . . . . ?
C7 N2 C6 O1 3.5(3) . . . . ?
C27 N2 C6 C5 -1.5(3) . . . . ?
C7 N2 C6 C5 -175.52(17) . . . . ?
C1 C5 C6 O1 -178.97(19) . . . . ?
C26 C5 C6 O1 0.0(3) . . . . ?
C1 C5 C6 N2 0.0(3) . . . . ?
C26 C5 C6 N2 178.96(18) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
C14 C15 C16 C17 178.59(19) . . . . ?
C13 N3 C8 C7 -59.1(2) . . . . ?
C9 N3 C8 C7 177.37(17) . . . . ?
C6 N2 C7 C8 -74.7(2) . . . . ?
C27 N2 C7 C8 110.8(2) . . . . ?
N3 C8 C7 N2 -69.0(2) . . . . ?
C23 C22 C21 O4 4.9(4) . . . . ?
C23 C22 C21 O5 -174.9(2) . . . . ?
C16 C15 C14 O3 -171.6(2) . . . . ?
C20 C15 C14 O3 7.4(3) . . . . ?
C16 C15 C14 C11 8.9(3) . . . . ?
C20 C15 C14 C11 -172.08(18) . . . . ?
C12 C11 C14 O3 10.1(3) . . . . ?
C10 C11 C14 O3 -111.8(2) . . . . ?
C12 C11 C14 C15 -170.42(17) . . . . ?
C10 C11 C14 C15 67.6(2) . . . . ?
C16 C15 C20 C19 0.8(3) . . . . ?
C14 C15 C20 C19 -178.29(19) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C15 C20 C19 C18 -0.4(3) . . . . ?
C1 C5 C26 C4 0.0(3) . . . . ?
C6 C5 C26 C4 -179.0(2) . . . . ?
C16 C17 C18 F -179.21(19) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C20 C19 C18 F 179.54(19) . . . . ?
C20 C19 C18 C17 -0.4(3) . . . . ?
C5 C26 C4 C3 -0.3(3) . . . . ?
N1 C1 C2 C3 178.3(2) . . . . ?
C5 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C26 C4 C3 C2 -0.1(4) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_kts_sul_0m
_database_code_depnum_ccdc_archive 'CCDC 2372347'
loop_
_audit_author_name
_audit_author_address
'SMRUTI REKHA ROUT'
;INSTITUTION OF CHEMICAL TECHNOLOGY
India
;
_audit_update_record             
;
2024-07-21 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-07-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H2 N O3 S, C22 H23 F N3 O3, 2(H2 O)'
_chemical_formula_sum            'C22 H29 F N4 O8 S'
_chemical_formula_weight         528.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.104(3)
_cell_length_b                   10.937(4)
_cell_length_c                   12.774(5)
_cell_angle_alpha                86.214(11)
_cell_angle_beta                 71.917(10)
_cell_angle_gamma                82.894(12)
_cell_volume                     1199.3(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    301.00
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1459 before and 0.0865 after correction.
The Ratio of minimum to maximum transmission is 0.8513.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18053
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_temperature      301.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2183
_reflns_number_total             4199
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4199
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.1757
_refine_ls_R_factor_gt           0.0902
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1371P)²+0.2536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2316
_refine_ls_wR_factor_ref         0.2646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 S1-O5 \\sim S2-O6
 with sigma of 0.02
 S1-O7 \\sim S2-O9
 with sigma of 0.02
 S1-N4 \\sim S2-N5
 with sigma of 0.02
 O5-O7 \\sim O6-O9
 with sigma of 0.04
 O5-N4 \\sim O6-N5
 with sigma of 0.04
 O7-N4 \\sim O9-N5
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(S2)
4. Rigid body (RIGU) restrains
 S1, S2, O4, O5, O6, O7, O9, N4, N5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1, S2
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
5. Others
 Sof(S2)=Sof(O6)=Sof(O9)=Sof(N5)=Sof(H5A)=Sof(H5B)=1-FVAR(1)
 Sof(S1)=Sof(O4)=Sof(O7)=Sof(N4)=Sof(H4A)=Sof(H4B)=FVAR(1)
6.a Riding coordinates:
 O8(H8A,H8B), O10(H10C,H10D)
6.b Ternary CH refined with riding coordinates:
 N3(H3), C13(H13)
6.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C15(H15A,H15B)
6.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3A), C4(H4), C5(H5), C18(H18), C19(H19), C21(H21),
 C22(H22)
6.e X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.2808(11) 0.1605(8) 0.4821(5) 0.0832(8) Uani 0.821(12) 1 d D . P A 1
S2 S 1.288(5) 0.159(3) 0.470(2) 0.0832(8) Uani 0.179(12) 1 d D . P A 2
O4 O 1.2560(6) 0.2861(5) 0.4305(6) 0.112(3) Uani 0.821(12) 1 d . . P A 1
O5 O 1.1376(4) 0.1065(4) 0.5142(4) 0.0945(14) Uani 1 1 d D . . . .
O6 O 1.282(4) 0.242(3) 0.552(3) 0.122(12) Uani 0.179(12) 1 d D . P A 2
O7 O 1.3645(8) 0.1579(12) 0.5544(5) 0.152(5) Uani 0.821(12) 1 d D . P A 1
O9 O 1.328(4) 0.194(4) 0.361(2) 0.137(17) Uani 0.179(12) 1 d D . P A 2
N4 N 1.3961(7) 0.0868(7) 0.3788(6) 0.102(3) Uani 0.821(12) 1 d D . P A 1
H4A H 1.487708 0.056886 0.379641 0.123 Uiso 0.821(12) 1 calc R U P A 1
H4B H 1.366499 0.077029 0.322459 0.123 Uiso 0.821(12) 1 calc R U P A 1
N5 N 1.408(3) 0.045(2) 0.485(3) 0.111(14) Uani 0.179(12) 1 d D . P A 2
H5A H 1.481368 0.016576 0.429174 0.133 Uiso 0.179(12) 1 calc R U P A 2
H5B H 1.398692 0.012338 0.549698 0.133 Uiso 0.179(12) 1 calc R U P A 2
F1 F 0.0735(4) 0.4259(4) 1.1447(3) 0.0963(12) Uani 1 1 d . . . . .
O1 O 1.1815(4) 0.0477(3) 0.2287(3) 0.0767(11) Uani 1 1 d . . . . .
O2 O 0.7363(5) 0.2612(4) 0.1921(3) 0.0930(14) Uani 1 1 d . . . . .
O3 O 0.7742(4) 0.2883(4) 0.8843(3) 0.0851(13) Uani 1 1 d . . . . .
N1 N 0.9564(5) 0.1496(3) 0.2117(3) 0.0547(10) Uani 1 1 d . . . . .
N2 N 0.9308(5) 0.2043(4) 0.0391(3) 0.0652(12) Uani 1 1 d . . . . .
H2 H 0.877825 0.242048 -0.000919 0.078 Uiso 1 1 calc R U . . .
N3 N 0.8664(4) 0.2551(3) 0.5012(3) 0.0470(10) Uani 1 1 d . . . . .
H3 H 0.934632 0.187000 0.520711 0.056 Uiso 1 1 calc R U . . .
C1 C 1.0732(5) 0.1441(4) -0.0151(4) 0.0507(12) Uani 1 1 d . . . . .
C2 C 1.1273(6) 0.1383(5) -0.1288(4) 0.0617(14) Uani 1 1 d . . . . .
H2A H 1.068010 0.177601 -0.171396 0.074 Uiso 1 1 calc R U . . .
C3 C 1.2709(6) 0.0734(5) -0.1790(4) 0.0701(15) Uani 1 1 d . . . . .
H3A H 1.308156 0.070581 -0.255415 0.084 Uiso 1 1 calc R U . . .
C4 C 1.3582(6) 0.0135(6) -0.1170(5) 0.0783(17) Uani 1 1 d . . . . .
H4 H 1.453280 -0.031026 -0.150896 0.094 Uiso 1 1 calc R U . . .
C5 C 1.3034(6) 0.0200(5) -0.0038(4) 0.0669(15) Uani 1 1 d . . . . .
H5 H 1.363713 -0.019652 0.037850 0.080 Uiso 1 1 calc R U . . .
C6 C 1.1614(5) 0.0838(4) 0.0496(4) 0.0497(12) Uani 1 1 d . . . . .
C7 C 1.1061(6) 0.0896(4) 0.1679(4) 0.0523(12) Uani 1 1 d . . . . .
C8 C 0.8668(6) 0.2096(5) 0.1485(4) 0.0626(14) Uani 1 1 d . . . . .
C9 C 0.8864(6) 0.1474(5) 0.3308(4) 0.0604(13) Uani 1 1 d . . . . .
H9A H 0.934427 0.076825 0.362933 0.073 Uiso 1 1 calc R U . . .
H9B H 0.776481 0.138899 0.348746 0.073 Uiso 1 1 calc R U . . .
C10 C 0.9071(6) 0.2638(5) 0.3788(3) 0.0546(12) Uani 1 1 d . . . . .
H10A H 1.014335 0.280984 0.348047 0.066 Uiso 1 1 calc R U . . .
H10B H 0.841980 0.331950 0.357962 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8958(6) 0.3726(5) 0.5441(4) 0.0604(13) Uani 1 1 d . . . . .
H11A H 1.003003 0.388137 0.509066 0.073 Uiso 1 1 calc R U . . .
H11B H 0.829211 0.441495 0.525950 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8639(6) 0.3620(6) 0.6671(4) 0.0697(15) Uani 1 1 d . . . . .
H12A H 0.884423 0.437484 0.693208 0.084 Uiso 1 1 calc R U . . .
H12B H 0.933343 0.294869 0.684862 0.084 Uiso 1 1 calc R U . . .
C13 C 0.6971(5) 0.3386(4) 0.7252(3) 0.0506(12) Uani 1 1 d . . . . .
H13 H 0.628064 0.408909 0.710004 0.061 Uiso 1 1 calc R U . . .
C14 C 0.6642(6) 0.2238(5) 0.6798(3) 0.0561(13) Uani 1 1 d . . . . .
H14A H 0.724712 0.152718 0.701022 0.067 Uiso 1 1 calc R U . . .
H14B H 0.555123 0.212547 0.712352 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7024(6) 0.2297(5) 0.5554(4) 0.0594(13) Uani 1 1 d . . . . .
H15A H 0.686219 0.152068 0.530480 0.071 Uiso 1 1 calc R U . . .
H15B H 0.632892 0.294204 0.534276 0.071 Uiso 1 1 calc R U . . .
C16 C 0.6654(6) 0.3234(5) 0.8494(4) 0.0584(13) Uani 1 1 d . . . . .
C17 C 0.5055(5) 0.3491(4) 0.9260(4) 0.0512(12) Uani 1 1 d . . . . .
C18 C 0.4804(6) 0.3266(4) 1.0377(4) 0.0582(13) Uani 1 1 d . . . . .
H18 H 0.562620 0.294215 1.063355 0.070 Uiso 1 1 calc R U . . .
C19 C 0.3348(7) 0.3520(5) 1.1108(4) 0.0661(15) Uani 1 1 d . . . . .
H19 H 0.317154 0.336223 1.185847 0.079 Uiso 1 1 calc R U . . .
C20 C 0.2166(6) 0.4005(5) 1.0715(4) 0.0644(14) Uani 1 1 d . . . . .
C21 C 0.2362(6) 0.4247(5) 0.9633(4) 0.0697(15) Uani 1 1 d . . . . .
H21 H 0.153450 0.458836 0.938844 0.084 Uiso 1 1 calc R U . . .
C22 C 0.3813(6) 0.3976(5) 0.8905(4) 0.0632(14) Uani 1 1 d . . . . .
H22 H 0.396448 0.412135 0.815530 0.076 Uiso 1 1 calc R U . . .
O8 O 0.5211(6) 0.4079(5) 0.3539(5) 0.1305(18) Uani 1 1 d . . . . .
H8A H 0.440540 0.361562 0.368943 0.196 Uiso 1 1 d R U . . .
H8B H 0.605070 0.360872 0.304543 0.196 Uiso 1 1 d R U . . .
O10 O 0.7253(11) 0.5670(8) 0.3634(8) 0.240(4) Uani 1 1 d . . . . .
H10C H 0.631142 0.551564 0.383121 0.360 Uiso 1 1 d R U . . .
H10D H 0.722452 0.634874 0.393171 0.360 Uiso 1 1 d 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 O4 1.506(9) . ?
S1 O5 1.429(13) . ?
S1 O7 1.365(10) . ?
S1 N4 1.601(8) . ?
S2 O5 1.49(5) . ?
S2 O6 1.42(3) . ?
S2 O9 1.37(2) . ?
S2 N5 1.60(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F1 C20 1.356(5) . ?
O1 C7 1.220(5) . ?
O2 C8 1.227(6) . ?
O3 C16 1.219(6) . ?
N1 C7 1.398(6) . ?
N1 C8 1.398(6) . ?
N1 C9 1.456(6) . ?
N2 H2 0.8600 . ?
N2 C1 1.373(6) . ?
N2 C8 1.339(6) . ?
N3 H3 0.9800 . ?
N3 C10 1.489(5) . ?
N3 C11 1.514(6) . ?
N3 C15 1.491(6) . ?
C1 C2 1.385(6) . ?
C1 C6 1.404(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.391(7) . ?
C3 H3A 0.9300 . ?
C3 C4 1.372(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(6) . ?
C6 C7 1.439(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.505(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.506(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.515(6) . ?
C13 H13 0.9800 . ?
C13 C14 1.517(6) . ?
C13 C16 1.523(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.516(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.486(6) . ?
C17 C18 1.383(6) . ?
C17 C22 1.380(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.361(7) . ?
C20 C21 1.350(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.369(7) . ?
C22 H22 0.9300 . ?
O8 H8A 0.9079 . ?
O8 H8B 0.9450 . ?
O10 H10C 0.8502 . ?
O10 H10D 0.8501 . ?

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
O4 S1 N4 101.5(6) . . ?
O5 S1 O4 108.7(6) . . ?
O5 S1 N4 107.4(7) . . ?
O7 S1 O4 113.6(9) . . ?
O7 S1 O5 119.6(6) . . ?
O7 S1 N4 104.2(7) . . ?
O5 S2 N5 102(3) . . ?
O6 S2 O5 103(2) . . ?
O6 S2 N5 105(3) . . ?
O9 S2 O5 115(3) . . ?
O9 S2 O6 122(4) . . ?
O9 S2 N5 109(2) . . ?
S1 N4 H4A 120.0 . . ?
S1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
S2 N5 H5A 120.0 . . ?
S2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 N1 C8 124.4(4) . . ?
C7 N1 C9 118.4(4) . . ?
C8 N1 C9 117.2(4) . . ?
C1 N2 H2 117.0 . . ?
C8 N2 H2 117.0 . . ?
C8 N2 C1 126.0(4) . . ?
C10 N3 H3 108.0 . . ?
C10 N3 C11 110.0(3) . . ?
C10 N3 C15 112.7(3) . . ?
C11 N3 H3 108.0 . . ?
C15 N3 H3 108.0 . . ?
C15 N3 C11 110.0(3) . . ?
N2 C1 C2 122.1(4) . . ?
N2 C1 C6 117.4(4) . . ?
C2 C1 C6 120.5(4) . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.5(5) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(5) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(5) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 120.8(4) . . ?
C5 C6 C1 118.0(4) . . ?
C5 C6 C7 121.2(4) . . ?
O1 C7 N1 120.3(4) . . ?
O1 C7 C6 124.3(4) . . ?
N1 C7 C6 115.4(4) . . ?
O2 C8 N1 121.1(5) . . ?
O2 C8 N2 122.9(4) . . ?
N2 C8 N1 115.9(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 C10 110.7(4) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
N3 C10 C9 112.5(4) . . ?
N3 C10 H10A 109.1 . . ?
N3 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N3 C11 H11A 109.6 . . ?
N3 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 N3 110.4(4) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C11 C12 C13 111.3(4) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13 108.7 . . ?
C12 C13 C14 108.9(4) . . ?
C12 C13 C16 111.6(4) . . ?
C14 C13 H13 108.7 . . ?
C14 C13 C16 110.2(4) . . ?
C16 C13 H13 108.7 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 112.9(4) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
N3 C15 C14 111.3(4) . . ?
N3 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O3 C16 C13 118.4(4) . . ?
O3 C16 C17 120.8(4) . . ?
C17 C16 C13 120.8(4) . . ?
C18 C17 C16 118.9(4) . . ?
C22 C17 C16 122.6(4) . . ?
C22 C17 C18 118.5(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(5) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.8(5) . . ?
C20 C19 H19 120.6 . . ?
F1 C20 C19 118.2(5) . . ?
C21 C20 F1 119.0(5) . . ?
C21 C20 C19 122.8(5) . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.1(5) . . ?
C22 C21 H21 120.9 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.4(5) . . ?
C21 C22 H22 119.3 . . ?
H8A O8 H8B 104.7 . . ?
H10C O10 H10D 104.5 . . ?

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
N2 H2 O3 0.86 1.98 2.823(5) 164.7 1_554 yes
N3 H3 O5 0.98 1.93 2.827(5) 151.7 . yes
O8 H8A O4 0.91 1.89 2.778(8) 166.7 1_455 yes
O8 H8B O2 0.94 1.87 2.799(6) 166.8 . yes
O10 H10C O8 0.85 2.08 2.732(11) 133.6 . yes
O10 H10D O6 0.85 1.54 2.39(2) 179.6 2_766 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
F1 C20 C21 C22 -179.5(5) . . . . ?
O3 C16 C17 C18 -3.2(8) . . . . ?
O3 C16 C17 C22 175.1(5) . . . . ?
N1 C9 C10 N3 -168.4(4) . . . . ?
N2 C1 C2 C3 -178.4(5) . . . . ?
N2 C1 C6 C5 178.4(4) . . . . ?
N2 C1 C6 C7 -2.4(7) . . . . ?
N3 C11 C12 C13 -59.7(6) . . . . ?
C1 N2 C8 O2 -177.2(5) . . . . ?
C1 N2 C8 N1 1.2(7) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C1 C6 C7 O1 -174.1(5) . . . . ?
C1 C6 C7 N1 5.0(6) . . . . ?
C2 C1 C6 C5 0.6(7) . . . . ?
C2 C1 C6 C7 179.8(4) . . . . ?
C2 C3 C4 C5 -1.2(9) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C4 C5 C6 C7 -180.0(5) . . . . ?
C5 C6 C7 O1 5.2(8) . . . . ?
C5 C6 C7 N1 -175.7(4) . . . . ?
C6 C1 C2 C3 -0.7(7) . . . . ?
C7 N1 C8 O2 -179.6(5) . . . . ?
C7 N1 C8 N2 1.9(7) . . . . ?
C7 N1 C9 C10 97.2(5) . . . . ?
C8 N1 C7 O1 174.2(4) . . . . ?
C8 N1 C7 C6 -4.9(7) . . . . ?
C8 N1 C9 C10 -84.4(5) . . . . ?
C8 N2 C1 C2 176.8(5) . . . . ?
C8 N2 C1 C6 -0.9(7) . . . . ?
C9 N1 C7 O1 -7.4(7) . . . . ?
C9 N1 C7 C6 173.4(4) . . . . ?
C9 N1 C8 O2 2.0(7) . . . . ?
C9 N1 C8 N2 -176.4(4) . . . . ?
C10 N3 C11 C12 -176.7(4) . . . . ?
C10 N3 C15 C14 -179.0(4) . . . . ?
C11 N3 C10 C9 177.7(4) . . . . ?
C11 N3 C15 C14 -55.9(5) . . . . ?
C11 C12 C13 C14 56.3(5) . . . . ?
C11 C12 C13 C16 178.1(4) . . . . ?
C12 C13 C14 C15 -54.0(5) . . . . ?
C12 C13 C16 O3 -25.3(7) . . . . ?
C12 C13 C16 C17 155.5(5) . . . . ?
C13 C14 C15 N3 55.0(5) . . . . ?
C13 C16 C17 C18 175.9(4) . . . . ?
C13 C16 C17 C22 -5.8(7) . . . . ?
C14 C13 C16 O3 95.7(6) . . . . ?
C14 C13 C16 C17 -83.4(5) . . . . ?
C15 N3 C10 C9 -59.3(5) . . . . ?
C15 N3 C11 C12 58.6(5) . . . . ?
C16 C13 C14 C15 -176.6(4) . . . . ?
C16 C17 C18 C19 178.5(4) . . . . ?
C16 C17 C22 C21 -177.5(5) . . . . ?
C17 C18 C19 C20 -0.7(8) . . . . ?
C18 C17 C22 C21 0.8(8) . . . . ?
C18 C19 C20 F1 -179.5(4) . . . . ?
C18 C19 C20 C21 0.2(8) . . . . ?
C19 C20 C21 C22 0.8(9) . . . . ?
C20 C21 C22 C17 -1.2(8) . . . . ?
C22 C17 C18 C19 0.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ket_maleic_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2372346'
loop_
_audit_author_name
_audit_author_address
'SMRUTI REKHA ROUT'
;INSTITUTION OF CHEMICAL TECHNOLOGY
India
;
_audit_update_record             
;
2024-07-21 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2023-11-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 F N3 O3, C4 H3 O4'
_chemical_formula_sum            'C26 H26 F N3 O7'
_chemical_formula_weight         511.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.0189(5)
_cell_length_b                   31.707(2)
_cell_length_c                   12.5009(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.981(2)
_cell_angle_gamma                90
_cell_volume                     2368.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4874
_cell_measurement_temperature    298
_cell_measurement_theta_max      0.978
_cell_measurement_theta_min      0.974
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40219
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.531
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2961
_reflns_number_total             4869
_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       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.9862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1476
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C10(H10A,H10B), C15(H15A,H15B), C11(H11A,H11B), C9(H9A,H9B),
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C25(H25), C21(H21), C24(H24), C18(H18), C5(H5), C19(H19), C2(H2),
 C4(H4), C3(H3A)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1199(3) 0.66852(5) 0.15911(14) 0.0556(5) Uani 1 1 d . . . . .
N3 N 0.3037(3) 0.72365(6) 0.13050(14) 0.0359(4) Uani 1 1 d . . . . .
O6 O 0.3212(3) 0.68610(6) 0.33174(13) 0.0578(5) Uani 1 1 d . . . . .
O2 O 0.4707(3) 0.58978(6) 0.08425(16) 0.0670(6) Uani 1 1 d . . . . .
O3 O 0.0036(3) 0.83887(6) 0.31670(17) 0.0708(6) Uani 1 1 d . . . . .
N2 N 0.1672(3) 0.62758(6) 0.11624(14) 0.0409(5) Uani 1 1 d . . . . .
O4 O 0.5965(3) 0.63159(7) 0.38317(16) 0.0689(6) Uani 1 1 d . . . . .
H4A H 0.503996 0.649937 0.364228 0.103 Uiso 1 1 calc R U . . .
F1 F 0.7161(4) 0.98240(6) 0.40375(16) 0.0987(7) Uani 1 1 d . . . . .
N1 N -0.0546(4) 0.60639(6) 0.24697(17) 0.0482(5) Uani 1 1 d . . . . .
O7 O 0.0594(4) 0.71753(7) 0.41263(17) 0.0875(7) Uani 1 1 d . . . . .
C14 C 0.4385(4) 0.78409(7) 0.24895(18) 0.0418(5) Uani 1 1 d . . . . .
H14A H 0.567863 0.801744 0.270485 0.050 Uiso 1 1 calc R U . . .
H14B H 0.395391 0.770766 0.313168 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3739(4) 0.69019(7) 0.05644(18) 0.0430(6) Uani 1 1 d . . . . .
H10A H 0.510159 0.677087 0.090415 0.052 Uiso 1 1 calc R U . . .
H10B H 0.408405 0.703569 -0.009339 0.052 Uiso 1 1 calc R U . . .
C15 C 0.5011(4) 0.75032(7) 0.17183(18) 0.0412(5) Uani 1 1 d . . . . .
H15A H 0.560745 0.763629 0.111526 0.049 Uiso 1 1 calc R U . . .
H15B H 0.617288 0.732496 0.208574 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1178(4) 0.75071(7) 0.07791(18) 0.0420(5) Uani 1 1 d . . . . .
H11A H -0.009971 0.733195 0.052510 0.050 Uiso 1 1 calc R U . . .
H11B H 0.166315 0.765044 0.016246 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2450(4) 0.81167(7) 0.19736(17) 0.0389(5) Uani 1 1 d . . . . .
H13 H 0.293805 0.826545 0.135566 0.047 Uiso 1 1 calc R U . . .
C7 C -0.0122(4) 0.63598(7) 0.17370(18) 0.0429(5) Uani 1 1 d . . . . .
O5 O 0.6609(4) 0.58649(8) 0.5162(2) 0.0974(8) Uani 1 1 d . . . . .
C9 C 0.2022(4) 0.65624(7) 0.02728(17) 0.0432(6) Uani 1 1 d . . . . .
H9A H 0.060662 0.669526 0.001418 0.052 Uiso 1 1 calc R U . . .
H9B H 0.248161 0.639706 -0.031518 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3227(4) 0.88079(7) 0.30710(17) 0.0415(5) Uani 1 1 d . . . . .
C16 C 0.1772(4) 0.84391(7) 0.27652(19) 0.0442(6) Uani 1 1 d . . . . .
C12 C 0.0506(4) 0.78282(7) 0.15713(19) 0.0432(5) Uani 1 1 d . . . . .
H12A H -0.000797 0.768341 0.217924 0.052 Uiso 1 1 calc R U . . .
H12B H -0.072518 0.799645 0.122735 0.052 Uiso 1 1 calc R U . . .
C6 C 0.0710(4) 0.57034(7) 0.26967(18) 0.0446(6) Uani 1 1 d . . . . .
C1 C 0.2558(4) 0.56329(7) 0.21624(19) 0.0453(6) Uani 1 1 d . . . . .
C22 C 0.5099(4) 0.89043(7) 0.25664(19) 0.0489(6) Uani 1 1 d . . . . .
H22 H 0.545948 0.873653 0.200211 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3115(4) 0.59312(7) 0.13491(19) 0.0453(6) Uani 1 1 d . . . . .
C25 C 0.1630(5) 0.64952(9) 0.47070(19) 0.0555(7) Uani 1 1 d . . . . .
H25 H 0.029079 0.647120 0.500328 0.067 Uiso 1 1 calc R U . . .
C21 C 0.6426(5) 0.92461(8) 0.2895(2) 0.0587(7) Uani 1 1 d . . . . .
H21 H 0.768253 0.931020 0.256003 0.070 Uiso 1 1 calc R U . . .
C24 C 0.3097(5) 0.61863(9) 0.49699(19) 0.0562(7) Uani 1 1 d . . . . .
H24 H 0.261970 0.598327 0.542819 0.067 Uiso 1 1 calc R U . . .
C26 C 0.1799(5) 0.68734(8) 0.40119(19) 0.0525(6) Uani 1 1 d . . . . .
C18 C 0.2709(5) 0.90654(8) 0.3908(2) 0.0532(7) Uani 1 1 d . . . . .
H18 H 0.145754 0.900556 0.425023 0.064 Uiso 1 1 calc R U . . .
C5 C 0.0176(5) 0.54187(8) 0.3473(2) 0.0596(7) Uani 1 1 d . . . . .
H5 H -0.106816 0.546428 0.383153 0.072 Uiso 1 1 calc R U . . .
C19 C 0.4029(5) 0.94076(8) 0.4236(2) 0.0642(8) Uani 1 1 d . . . . .
H19 H 0.368318 0.957979 0.479450 0.077 Uiso 1 1 calc R U . . .
C20 C 0.5855(5) 0.94879(8) 0.3720(2) 0.0619(7) Uani 1 1 d . . . . .
C23 C 0.5356(5) 0.61117(9) 0.4656(2) 0.0584(7) Uani 1 1 d . . . . .
C2 C 0.3886(5) 0.52776(8) 0.2415(2) 0.0635(8) Uani 1 1 d . . . . .
H2 H 0.513763 0.523012 0.206269 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1498(6) 0.50704(9) 0.3705(2) 0.0703(9) Uani 1 1 d . . . . .
H4 H 0.114006 0.487997 0.422353 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3351(6) 0.49984(9) 0.3180(2) 0.0739(9) Uani 1 1 d . . . . .
H3A H 0.423442 0.476102 0.334541 0.089 Uiso 1 1 calc R U . . .
H3 H 0.252(4) 0.7110(8) 0.191(2) 0.063(8) Uiso 1 1 d . . . . .
H1 H -0.165(5) 0.6115(9) 0.284(2) 0.077(10) 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
O1 C7 1.220(3) . ?
N3 C10 1.502(3) . ?
N3 C15 1.498(3) . ?
N3 C11 1.497(3) . ?
N3 H3 0.94(3) . ?
O6 C26 1.288(3) . ?
O2 C8 1.216(3) . ?
O3 C16 1.224(3) . ?
N2 C7 1.393(3) . ?
N2 C9 1.471(3) . ?
N2 C8 1.398(3) . ?
O4 H4A 0.8200 . ?
O4 C23 1.307(3) . ?
F1 C20 1.355(3) . ?
N1 C7 1.357(3) . ?
N1 C6 1.380(3) . ?
N1 H1 0.87(3) . ?
O7 C26 1.220(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.519(3) . ?
C14 C13 1.534(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.506(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(3) . ?
C13 H13 0.9800 . ?
C13 C16 1.513(3) . ?
C13 C12 1.522(3) . ?
O5 C23 1.211(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17 C16 1.483(3) . ?
C17 C22 1.391(3) . ?
C17 C18 1.392(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C1 1.384(3) . ?
C6 C5 1.391(3) . ?
C1 C8 1.457(3) . ?
C1 C2 1.395(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.379(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.333(4) . ?
C25 C26 1.492(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.363(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.479(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.377(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.371(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.380(4) . ?
C3 H3A 0.9300 . ?

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
C10 N3 H3 109.8(16) . . ?
C15 N3 C10 109.91(17) . . ?
C15 N3 H3 106.7(16) . . ?
C11 N3 C10 112.66(17) . . ?
C11 N3 C15 110.32(17) . . ?
C11 N3 H3 107.2(16) . . ?
C7 N2 C9 117.59(19) . . ?
C7 N2 C8 124.63(19) . . ?
C8 N2 C9 117.75(18) . . ?
C23 O4 H4A 109.5 . . ?
C7 N1 C6 124.6(2) . . ?
C7 N1 H1 117(2) . . ?
C6 N1 H1 119(2) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C15 C14 C13 111.67(18) . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
N3 C10 H10A 108.6 . . ?
N3 C10 H10B 108.6 . . ?
N3 C10 C9 114.71(18) . . ?
H10A C10 H10B 107.6 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
N3 C15 C14 111.66(18) . . ?
N3 C15 H15A 109.3 . . ?
N3 C15 H15B 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
N3 C11 H11A 109.6 . . ?
N3 C11 H11B 109.6 . . ?
N3 C11 C12 110.12(18) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C14 C13 H13 108.7 . . ?
C16 C13 C14 111.20(18) . . ?
C16 C13 H13 108.7 . . ?
C16 C13 C12 111.36(18) . . ?
C12 C13 C14 108.07(18) . . ?
C12 C13 H13 108.7 . . ?
O1 C7 N2 121.0(2) . . ?
O1 C7 N1 123.0(2) . . ?
N1 C7 N2 115.9(2) . . ?
N2 C9 C10 114.56(18) . . ?
N2 C9 H9A 108.6 . . ?
N2 C9 H9B 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C22 C17 C16 122.8(2) . . ?
C22 C17 C18 118.7(2) . . ?
C18 C17 C16 118.5(2) . . ?
O3 C16 C13 119.5(2) . . ?
O3 C16 C17 120.3(2) . . ?
C17 C16 C13 120.2(2) . . ?
C11 C12 C13 111.44(19) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N1 C6 C1 119.1(2) . . ?
N1 C6 C5 120.9(2) . . ?
C1 C6 C5 119.9(2) . . ?
C6 C1 C8 119.9(2) . . ?
C6 C1 C2 119.6(2) . . ?
C2 C1 C8 120.5(2) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.7(2) . . ?
C21 C22 H22 119.7 . . ?
O2 C8 N2 119.6(2) . . ?
O2 C8 C1 124.7(2) . . ?
N2 C8 C1 115.6(2) . . ?
C24 C25 H25 114.9 . . ?
C24 C25 C26 130.1(2) . . ?
C26 C25 H25 114.9 . . ?
C22 C21 H21 120.8 . . ?
C20 C21 C22 118.5(3) . . ?
C20 C21 H21 120.8 . . ?
C25 C24 H24 114.6 . . ?
C25 C24 C23 130.9(2) . . ?
C23 C24 H24 114.6 . . ?
O6 C26 C25 117.8(2) . . ?
O7 C26 O6 123.6(3) . . ?
O7 C26 C25 118.6(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.4(2) . . ?
C20 C19 H19 120.8 . . ?
F1 C20 C21 118.3(3) . . ?
F1 C20 C19 118.7(2) . . ?
C21 C20 C19 123.0(3) . . ?
O4 C23 C24 119.0(2) . . ?
O5 C23 O4 121.0(3) . . ?
O5 C23 C24 119.9(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 120.9(3) . . ?
C3 C4 H4 119.5 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C10 C9 N2 -70.2(3) . . . . ?
N3 C11 C12 C13 60.5(2) . . . . ?
N1 C6 C1 C8 -1.8(3) . . . . ?
N1 C6 C1 C2 177.6(2) . . . . ?
N1 C6 C5 C4 -177.9(3) . . . . ?
C14 C13 C16 O3 -105.5(3) . . . . ?
C14 C13 C16 C17 73.0(3) . . . . ?
C14 C13 C12 C11 -57.8(2) . . . . ?
C10 N3 C15 C14 -178.86(18) . . . . ?
C10 N3 C11 C12 178.40(18) . . . . ?
C15 N3 C10 C9 168.39(19) . . . . ?
C15 N3 C11 C12 -58.4(2) . . . . ?
C15 C14 C13 C16 177.43(18) . . . . ?
C15 C14 C13 C12 54.9(2) . . . . ?
C11 N3 C10 C9 -68.1(2) . . . . ?
C11 N3 C15 C14 56.3(2) . . . . ?
C13 C14 C15 N3 -55.5(2) . . . . ?
C7 N2 C9 C10 97.0(2) . . . . ?
C7 N2 C8 O2 -176.0(2) . . . . ?
C7 N2 C8 C1 4.0(3) . . . . ?
C7 N1 C6 C1 0.9(4) . . . . ?
C7 N1 C6 C5 179.1(2) . . . . ?
C9 N2 C7 O1 -8.3(3) . . . . ?
C9 N2 C7 N1 172.89(19) . . . . ?
C9 N2 C8 O2 6.2(3) . . . . ?
C9 N2 C8 C1 -173.81(19) . . . . ?
C17 C22 C21 C20 -0.3(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C16 C13 C12 C11 179.84(18) . . . . ?
C16 C17 C22 C21 -178.7(2) . . . . ?
C16 C17 C18 C19 178.9(2) . . . . ?
C12 C13 C16 O3 15.1(3) . . . . ?
C12 C13 C16 C17 -166.4(2) . . . . ?
C6 N1 C7 O1 -176.4(2) . . . . ?
C6 N1 C7 N2 2.3(3) . . . . ?
C6 C1 C8 O2 179.6(3) . . . . ?
C6 C1 C8 N2 -0.5(3) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C6 C5 C4 C3 0.0(5) . . . . ?
C1 C6 C5 C4 0.3(4) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C22 C17 C16 O3 -173.5(2) . . . . ?
C22 C17 C16 C13 7.9(3) . . . . ?
C22 C17 C18 C19 -0.3(4) . . . . ?
C22 C21 C20 F1 -179.8(3) . . . . ?
C22 C21 C20 C19 -0.1(5) . . . . ?
C8 N2 C7 O1 173.8(2) . . . . ?
C8 N2 C7 N1 -4.9(3) . . . . ?
C8 N2 C9 C10 -85.0(2) . . . . ?
C8 C1 C2 C3 -180.0(3) . . . . ?
C25 C24 C23 O4 -16.0(5) . . . . ?
C25 C24 C23 O5 163.8(3) . . . . ?
C24 C25 C26 O6 21.8(4) . . . . ?
C24 C25 C26 O7 -158.5(3) . . . . ?
C26 C25 C24 C23 -0.8(5) . . . . ?
C18 C17 C16 O3 7.3(4) . . . . ?
C18 C17 C16 C13 -171.3(2) . . . . ?
C18 C17 C22 C21 0.5(4) . . . . ?
C18 C19 C20 F1 180.0(3) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C5 C6 C1 C8 180.0(2) . . . . ?
C5 C6 C1 C2 -0.6(4) . . . . ?
C5 C4 C3 C2 0.0(5) . . . . ?
C2 C1 C8 O2 0.1(4) . . . . ?
C2 C1 C8 N2 -179.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_ketsulf_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 2372349'
loop_
_audit_author_name
_audit_author_address
'SMRUTI REKHA ROUT'
;INSTITUTION OF CHEMICAL TECHNOLOGY
India
;
_audit_update_record             
;
2024-07-21 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_audit_creation_date             2024-07-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H3 N O3 S, C22 H23 F N3 O3, H2 O'
_chemical_formula_sum            'C22 H28 F N4 O7 S'
_chemical_formula_weight         511.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.554(3)
_cell_length_b                   10.936(5)
_cell_length_c                   12.526(5)
_cell_angle_alpha                85.91(2)
_cell_angle_beta                 76.418(19)
_cell_angle_gamma                87.737(17)
_cell_volume                     1135.8(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4102
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.746
_cell_measurement_theta_min      0.646
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             538
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.429
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4102
_reflns_number_total             5194
_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       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.192
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         5194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.051
_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)+(0.0454P)²+0.7295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C11(H11A,H11B), C15(H15A,H15B), C14(H14A,H14B),
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C19(H19), C21(H21), C18(H18), C5(H5), C4(H4), C2(H2A), C3(H3A)
2.d Idealised Me refined as rotating group:
 N4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22836(6) 0.72648(4) 0.53181(4) 0.01581(12) Uani 1 1 d . . . . .
F1 F 0.10848(14) 0.50076(11) 1.13692(10) 0.0216(3) Uani 1 1 d . . . . .
O1 O 1.21441(16) 0.87461(13) 0.22017(11) 0.0168(3) Uani 1 1 d . . . . .
O2 O 0.77389(16) 0.68879(13) 0.16672(11) 0.0169(3) Uani 1 1 d . . . . .
O3 O 0.73272(16) 0.77035(14) 0.87936(11) 0.0192(3) Uani 1 1 d . . . . .
O7 O 0.57222(19) 0.55747(15) 0.34340(13) 0.0226(3) Uani 1 1 d . . . . .
O6 O 0.31843(18) 0.68881(14) 0.61351(12) 0.0227(3) Uani 1 1 d . . . . .
O4 O 0.12087(17) 0.83330(13) 0.55792(12) 0.0225(3) Uani 1 1 d . . . . .
O5 O 0.14039(18) 0.62618(14) 0.50400(13) 0.0251(3) Uani 1 1 d . . . . .
N1 N 1.00281(18) 0.77199(14) 0.19179(12) 0.0112(3) Uani 1 1 d . . . . .
N2 N 0.94333(19) 0.77944(15) 0.01838(13) 0.0137(3) Uani 1 1 d . . . . .
N3 N 0.82802(19) 0.79232(14) 0.49676(12) 0.0110(3) Uani 1 1 d . . . . .
N4 N 0.3660(2) 0.77349(16) 0.42142(14) 0.0198(4) Uani 1 1 d . . . . .
H4A H 0.425025 0.832989 0.439265 0.030 Uiso 1 1 calc R U . . .
H4B H 0.316662 0.804127 0.367974 0.030 Uiso 1 1 calc R U . . .
H4C H 0.431902 0.709165 0.396389 0.030 Uiso 1 1 calc R U . . .
C7 C 1.1354(2) 0.84798(17) 0.15594(15) 0.0124(4) Uani 1 1 d . . . . .
C20 C 0.2324(2) 0.55900(17) 1.06454(16) 0.0145(4) Uani 1 1 d . . . . .
C9 C 0.9647(2) 0.72393(17) 0.30748(14) 0.0125(4) Uani 1 1 d . . . . .
H9A H 1.064724 0.711028 0.334087 0.015 Uiso 1 1 calc R U . . .
H9B H 0.910591 0.644414 0.314645 0.015 Uiso 1 1 calc R U . . .
C8 C 0.8981(2) 0.74375(17) 0.12728(15) 0.0129(4) Uani 1 1 d . . . . .
C17 C 0.4802(2) 0.67643(17) 0.91961(15) 0.0117(4) Uani 1 1 d . . . . .
C22 C 0.3550(2) 0.62964(17) 0.88184(15) 0.0131(4) Uani 1 1 d . . . . .
H22 H 0.355262 0.639456 0.805827 0.016 Uiso 1 1 calc R U . . .
C19 C 0.3524(2) 0.60494(17) 1.10590(15) 0.0153(4) Uani 1 1 d . . . . .
H19 H 0.349433 0.596426 1.182358 0.018 Uiso 1 1 calc R U . . .
C21 C 0.2297(2) 0.56866(17) 0.95486(16) 0.0143(4) Uani 1 1 d . . . . .
H21 H 0.145132 0.534872 0.929785 0.017 Uiso 1 1 calc R U . . .
C6 C 1.1705(2) 0.88892(16) 0.03865(15) 0.0128(4) Uani 1 1 d . . . . .
C1 C 1.0766(2) 0.84925(17) -0.02851(15) 0.0129(4) Uani 1 1 d . . . . .
C18 C 0.4773(2) 0.66383(17) 1.03229(15) 0.0126(4) Uani 1 1 d . . . . .
H18 H 0.562011 0.696058 1.058296 0.015 Uiso 1 1 calc R U . . .
C16 C 0.6200(2) 0.73757(17) 0.84403(15) 0.0124(4) Uani 1 1 d . . . . .
C13 C 0.6285(2) 0.75762(17) 0.72165(14) 0.0122(4) Uani 1 1 d . . . . .
H13 H 0.517413 0.757954 0.708888 0.015 Uiso 1 1 calc R U . . .
C5 C 1.3009(2) 0.96434(18) -0.00649(16) 0.0167(4) Uani 1 1 d . . . . .
H5 H 1.362315 0.994339 0.039723 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7073(2) 0.87885(18) 0.67595(15) 0.0160(4) Uani 1 1 d . . . . .
H12A H 0.640736 0.947348 0.711688 0.019 Uiso 1 1 calc R U . . .
H12B H 0.814450 0.880831 0.692980 0.019 Uiso 1 1 calc R U . . .
C4 C 1.3405(2) 0.99529(18) -0.11838(17) 0.0187(4) Uani 1 1 d . . . . .
H4 H 1.428382 1.047164 -0.149184 0.022 Uiso 1 1 calc R U . . .
C11 C 0.7257(2) 0.89529(17) 0.55253(15) 0.0156(4) Uani 1 1 d . . . . .
H11A H 0.618348 0.896221 0.535425 0.019 Uiso 1 1 calc R U . . .
H11B H 0.776364 0.974701 0.524557 0.019 Uiso 1 1 calc R U . . .
C2 C 1.1175(2) 0.87841(18) -0.14225(16) 0.0172(4) Uani 1 1 d . . . . .
H2A H 1.055257 0.849704 -0.188543 0.021 Uiso 1 1 calc R U . . .
C15 C 0.7538(2) 0.67052(17) 0.53739(15) 0.0134(4) Uani 1 1 d . . . . .
H15A H 0.824591 0.604084 0.501529 0.016 Uiso 1 1 calc R U . . .
H15B H 0.648809 0.666846 0.517501 0.016 Uiso 1 1 calc R U . . .
C3 C 1.2503(2) 0.94977(18) -0.18591(16) 0.0192(4) Uani 1 1 d . . . . .
H3A H 1.280669 0.968171 -0.263159 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7297(2) 0.65159(17) 0.66163(14) 0.0137(4) Uani 1 1 d . . . . .
H14A H 0.835944 0.646065 0.680546 0.016 Uiso 1 1 calc R U . . .
H14B H 0.674836 0.573205 0.687237 0.016 Uiso 1 1 calc R U . . .
C10 C 0.8540(2) 0.81760(17) 0.37515(14) 0.0131(4) Uani 1 1 d . . . . .
H10A H 0.900434 0.899895 0.355045 0.016 Uiso 1 1 calc R U . . .
H10B H 0.748448 0.819320 0.355379 0.016 Uiso 1 1 calc R U . . .
H2 H 0.874(3) 0.762(2) -0.022(2) 0.026(7) Uiso 1 1 d . . . . .
H7A H 0.644(4) 0.590(3) 0.289(3) 0.053(9) Uiso 1 1 d . . . . .
H7B H 0.609(4) 0.488(3) 0.361(2) 0.042(8) Uiso 1 1 d . . . . .
H3 H 0.926(3) 0.792(2) 0.514(2) 0.027(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 1.4478(15) . ?
S1 O4 1.4648(16) . ?
S1 O5 1.4607(16) . ?
S1 N4 1.6565(18) . ?
F1 C20 1.368(2) . ?
O1 C7 1.222(2) . ?
O2 C8 1.223(2) . ?
O3 C16 1.227(2) . ?
O7 H7A 0.86(4) . ?
O7 H7B 0.84(3) . ?
N1 C7 1.400(2) . ?
N1 C9 1.471(2) . ?
N1 C8 1.395(2) . ?
N2 C8 1.360(2) . ?
N2 C1 1.385(2) . ?
N2 H2 0.90(3) . ?
N3 C11 1.507(2) . ?
N3 C15 1.502(2) . ?
N3 C10 1.494(2) . ?
N3 H3 0.91(3) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
C7 C6 1.469(3) . ?
C20 C19 1.379(3) . ?
C20 C21 1.376(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(2) . ?
C17 C22 1.396(3) . ?
C17 C18 1.403(3) . ?
C17 C16 1.488(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.393(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.383(3) . ?
C21 H21 0.9500 . ?
C6 C1 1.392(3) . ?
C6 C5 1.398(3) . ?
C1 C2 1.401(3) . ?
C18 H18 0.9500 . ?
C16 C13 1.518(3) . ?
C13 H13 1.0000 . ?
C13 C12 1.523(3) . ?
C13 C14 1.549(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.383(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.515(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.398(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.521(3) . ?
C3 H3A 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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 O4 114.84(9) . . ?
O6 S1 O5 112.79(9) . . ?
O6 S1 N4 104.79(9) . . ?
O4 S1 N4 104.62(9) . . ?
O5 S1 O4 110.11(10) . . ?
O5 S1 N4 109.09(10) . . ?
H7A O7 H7B 107(3) . . ?
C7 N1 C9 118.03(15) . . ?
C8 N1 C7 124.66(15) . . ?
C8 N1 C9 117.21(15) . . ?
C8 N2 C1 124.25(17) . . ?
C8 N2 H2 115.3(16) . . ?
C1 N2 H2 120.1(16) . . ?
C11 N3 H3 108.5(16) . . ?
C15 N3 C11 110.85(14) . . ?
C15 N3 H3 107.8(16) . . ?
C10 N3 C11 108.28(14) . . ?
C10 N3 C15 113.52(14) . . ?
C10 N3 H3 107.8(16) . . ?
S1 N4 H4A 109.5 . . ?
S1 N4 H4B 109.5 . . ?
S1 N4 H4C 109.5 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
O1 C7 N1 120.32(17) . . ?
O1 C7 C6 124.40(18) . . ?
N1 C7 C6 115.28(16) . . ?
F1 C20 C19 118.04(17) . . ?
F1 C20 C21 118.08(17) . . ?
C21 C20 C19 123.88(18) . . ?
N1 C9 H9A 110.1 . . ?
N1 C9 H9B 110.1 . . ?
N1 C9 C10 107.92(14) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
O2 C8 N1 121.58(17) . . ?
O2 C8 N2 122.23(17) . . ?
N2 C8 N1 116.19(17) . . ?
C22 C17 C18 119.48(17) . . ?
C22 C17 C16 122.30(16) . . ?
C18 C17 C16 118.20(17) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.43(17) . . ?
C21 C22 H22 119.8 . . ?
C20 C19 H19 121.1 . . ?
C20 C19 C18 117.76(18) . . ?
C18 C19 H19 121.1 . . ?
C20 C21 C22 117.77(18) . . ?
C20 C21 H21 121.1 . . ?
C22 C21 H21 121.1 . . ?
C1 C6 C7 119.81(17) . . ?
C1 C6 C5 119.87(17) . . ?
C5 C6 C7 120.28(18) . . ?
N2 C1 C6 119.14(16) . . ?
N2 C1 C2 120.46(18) . . ?
C6 C1 C2 120.39(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.66(18) . . ?
C19 C18 H18 119.7 . . ?
O3 C16 C17 120.37(17) . . ?
O3 C16 C13 118.61(16) . . ?
C17 C16 C13 121.00(16) . . ?
C16 C13 H13 109.4 . . ?
C16 C13 C12 110.80(15) . . ?
C16 C13 C14 108.76(15) . . ?
C12 C13 H13 109.4 . . ?
C12 C13 C14 109.01(15) . . ?
C14 C13 H13 109.4 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.03(19) . . ?
C4 C5 H5 120.0 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C11 C12 C13 110.89(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.59(19) . . ?
C3 C4 H4 120.2 . . ?
N3 C11 C12 110.14(15) . . ?
N3 C11 H11A 109.6 . . ?
N3 C11 H11B 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 C1 118.80(19) . . ?
C3 C2 H2A 120.6 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 C14 110.58(15) . . ?
H15A C15 H15B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 C4 121.19(18) . . ?
C2 C3 H3A 119.4 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 C13 111.69(15) . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N3 C10 C9 114.08(15) . . ?
N3 C10 H10A 108.7 . . ?
N3 C10 H10B 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?

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
F1 C20 C19 C18 -179.94(16) . . . . ?
F1 C20 C21 C22 179.08(16) . . . . ?
O1 C7 C6 C1 177.41(17) . . . . ?
O1 C7 C6 C5 -0.6(3) . . . . ?
O3 C16 C13 C12 -37.5(2) . . . . ?
O3 C16 C13 C14 82.3(2) . . . . ?
N1 C7 C6 C1 -1.5(2) . . . . ?
N1 C7 C6 C5 -179.49(16) . . . . ?
N1 C9 C10 N3 -169.78(15) . . . . ?
N2 C1 C2 C3 179.13(17) . . . . ?
N3 C15 C14 C13 55.6(2) . . . . ?
C7 N1 C9 C10 87.97(19) . . . . ?
C7 N1 C8 O2 -171.23(17) . . . . ?
C7 N1 C8 N2 9.6(3) . . . . ?
C7 C6 C1 N2 5.1(3) . . . . ?
C7 C6 C1 C2 -174.17(16) . . . . ?
C7 C6 C5 C4 175.29(17) . . . . ?
C20 C19 C18 C17 0.3(3) . . . . ?
C9 N1 C7 O1 -1.2(2) . . . . ?
C9 N1 C7 C6 177.73(15) . . . . ?
C9 N1 C8 O2 5.0(3) . . . . ?
C9 N1 C8 N2 -174.20(15) . . . . ?
C8 N1 C7 O1 174.98(16) . . . . ?
C8 N1 C7 C6 -6.0(2) . . . . ?
C8 N1 C9 C10 -88.54(19) . . . . ?
C8 N2 C1 C6 -1.5(3) . . . . ?
C8 N2 C1 C2 177.80(17) . . . . ?
C17 C22 C21 C20 1.4(3) . . . . ?
C17 C16 C13 C12 144.17(17) . . . . ?
C17 C16 C13 C14 -96.03(19) . . . . ?
C22 C17 C18 C19 0.4(3) . . . . ?
C22 C17 C16 O3 -175.21(17) . . . . ?
C22 C17 C16 C13 3.1(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C21 C20 C19 C18 -0.2(3) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C1 N2 C8 O2 175.20(17) . . . . ?
C1 N2 C8 N1 -5.6(3) . . . . ?
C1 C6 C5 C4 -2.7(3) . . . . ?
C1 C2 C3 C4 -1.7(3) . . . . ?
C18 C17 C22 C21 -1.3(3) . . . . ?
C18 C17 C16 O3 3.5(3) . . . . ?
C18 C17 C16 C13 -178.19(16) . . . . ?
C16 C17 C22 C21 177.38(17) . . . . ?
C16 C17 C18 C19 -178.32(16) . . . . ?
C16 C13 C12 C11 176.37(15) . . . . ?
C16 C13 C14 C15 -175.82(15) . . . . ?
C13 C12 C11 N3 -59.6(2) . . . . ?
C5 C6 C1 N2 -176.94(17) . . . . ?
C5 C6 C1 C2 3.8(3) . . . . ?
C5 C4 C3 C2 2.8(3) . . . . ?
C12 C13 C14 C15 -54.9(2) . . . . ?
C11 N3 C15 C14 -57.4(2) . . . . ?
C11 N3 C10 C9 176.58(15) . . . . ?
C15 N3 C11 C12 59.4(2) . . . . ?
C15 N3 C10 C9 -59.9(2) . . . . ?
C14 C13 C12 C11 56.7(2) . . . . ?
C10 N3 C11 C12 -175.44(15) . . . . ?
C10 N3 C15 C14 -179.53(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
