# 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_rd602
_database_code_depnum_ccdc_archive 'CCDC 2494463'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.02.27 svn.r83f5de2 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
alex@xrlab.ineos.ac.ru
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Cl N O4'
_chemical_formula_sum            'C16 H10 Cl N O4'
_chemical_formula_weight         315.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3234(18)
_cell_length_b                   15.735(3)
_cell_length_c                   7.5713(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.695(5)
_cell_angle_gamma                90
_cell_volume                     1333.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    120
_cell_measurement_theta_max      22.10
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1229 before and 0.1007 after correction.
The Ratio of minimum to maximum transmission is 0.6207.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             648
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14733
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.819
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2050
_reflns_number_total             2944
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.027
_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)+(0.0740P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1548
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.45549(6) 0.67928(5) 0.15531(9) 0.0353(2) Uani 1 1 d . . . . .
O1 O 0.63543(14) 0.58315(11) 0.7894(2) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.70172(15) 0.63758(11) 0.2967(2) 0.0259(4) Uani 1 1 d . . . . .
O3 O 0.91405(14) 0.73932(10) 0.6136(2) 0.0238(4) Uani 1 1 d . . . . .
O4 O 1.05471(15) 0.81460(10) 0.7885(2) 0.0265(5) Uani 1 1 d . . . . .
N1 N 0.76293(18) 0.63404(13) 0.5967(3) 0.0216(5) Uani 1 1 d . . . . .
C1 C 0.6766(2) 0.63420(15) 0.4465(3) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.5532(2) 0.62392(14) 0.4900(3) 0.0206(6) Uani 1 1 d . . . . .
C3 C 0.5379(2) 0.59338(15) 0.6575(3) 0.0207(6) Uani 1 1 d . . . . .
C4 C 0.7248(2) 0.64453(16) 0.7693(3) 0.0239(6) Uani 1 1 d . . . . .
H4A H 0.793938 0.637201 0.865143 0.029 Uiso 1 1 calc R U . . .
H4B H 0.692400 0.702470 0.779233 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4275(2) 0.57060(16) 0.6994(3) 0.0260(6) Uani 1 1 d . . . . .
H5 H 0.420324 0.546682 0.812427 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3273(2) 0.58365(17) 0.5715(4) 0.0283(6) Uani 1 1 d . . . . .
H6 H 0.250648 0.568561 0.597850 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3376(2) 0.61813(16) 0.4071(4) 0.0262(6) Uani 1 1 d . . . . .
H7 H 0.268125 0.628672 0.322669 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4497(2) 0.63734(15) 0.3657(3) 0.0235(6) Uani 1 1 d . . . . .
C9 C 0.8846(2) 0.64970(15) 0.5760(4) 0.0206(6) Uani 1 1 d . . . . .
H9 H 0.894944 0.636850 0.449884 0.025 Uiso 1 1 calc R U . . .
C10 C 1.0148(2) 0.74644(16) 0.7389(3) 0.0214(6) Uani 1 1 d . . . . .
C11 C 1.0560(2) 0.66055(15) 0.7927(3) 0.0199(5) Uani 1 1 d . . . . .
C12 C 1.1544(2) 0.63537(16) 0.9133(3) 0.0234(6) Uani 1 1 d . . . . .
H12 H 1.206903 0.675874 0.976506 0.028 Uiso 1 1 calc R U . . .
C13 C 1.1732(2) 0.54890(16) 0.9379(3) 0.0239(6) Uani 1 1 d . . . . .
H13 H 1.240179 0.529500 1.018800 0.029 Uiso 1 1 calc R U . . .
C14 C 1.0945(2) 0.48963(17) 0.8450(3) 0.0242(6) Uani 1 1 d . . . . .
H14 H 1.109550 0.430628 0.862999 0.029 Uiso 1 1 calc R U . . .
C15 C 0.9950(2) 0.51574(15) 0.7269(3) 0.0212(6) Uani 1 1 d . . . . .
H15 H 0.940610 0.475573 0.666576 0.025 Uiso 1 1 calc R U . . .
C16 C 0.9778(2) 0.60218(16) 0.7000(3) 0.0202(5) Uani 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
Cl1 C8 1.735(3) . ?
O1 C3 1.382(3) . ?
O1 C4 1.424(3) . ?
O2 C1 1.211(3) . ?
O3 C9 1.467(3) . ?
O3 C10 1.374(3) . ?
O4 C10 1.202(3) . ?
N1 C1 1.383(3) . ?
N1 C4 1.446(3) . ?
N1 C9 1.431(3) . ?
C1 C2 1.492(3) . ?
C2 C3 1.391(3) . ?
C2 C8 1.404(3) . ?
C3 C5 1.383(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(4) . ?
C9 H9 1.0000 . ?
C9 C16 1.501(3) . ?
C10 C11 1.467(3) . ?
C11 C12 1.387(3) . ?
C11 C16 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.403(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C4 110.29(19) . . ?
C10 O3 C9 110.68(17) . . ?
C1 N1 C4 118.2(2) . . ?
C1 N1 C9 118.8(2) . . ?
C9 N1 C4 120.2(2) . . ?
O2 C1 N1 122.2(2) . . ?
O2 C1 C2 124.9(2) . . ?
N1 C1 C2 112.8(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 C8 117.2(2) . . ?
C8 C2 C1 123.4(2) . . ?
O1 C3 C2 120.2(2) . . ?
O1 C3 C5 117.1(2) . . ?
C5 C3 C2 122.7(2) . . ?
O1 C4 N1 109.46(19) . . ?
O1 C4 H4A 109.8 . . ?
O1 C4 H4B 109.8 . . ?
N1 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C3 C5 H5 120.9 . . ?
C3 C5 C6 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C2 C8 Cl1 121.9(2) . . ?
C7 C8 Cl1 117.0(2) . . ?
C7 C8 C2 121.1(2) . . ?
O3 C9 H9 108.9 . . ?
O3 C9 C16 103.87(19) . . ?
N1 C9 O3 109.80(19) . . ?
N1 C9 H9 108.9 . . ?
N1 C9 C16 116.3(2) . . ?
C16 C9 H9 108.9 . . ?
O3 C10 C11 108.2(2) . . ?
O4 C10 O3 121.5(2) . . ?
O4 C10 C11 130.3(2) . . ?
C12 C11 C10 129.5(2) . . ?
C12 C11 C16 122.1(2) . . ?
C16 C11 C10 108.5(2) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.4(2) . . ?
C13 C12 H12 121.3 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 121.1 . . ?
C16 C15 C14 117.9(2) . . ?
C16 C15 H15 121.1 . . ?
C11 C16 C9 108.7(2) . . ?
C15 C16 C9 130.6(2) . . ?
C15 C16 C11 120.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C5 C6 177.3(2) . . . . ?
O2 C1 C2 C3 159.0(2) . . . . ?
O2 C1 C2 C8 -15.9(4) . . . . ?
O3 C9 C16 C11 -2.6(3) . . . . ?
O3 C9 C16 C15 179.1(2) . . . . ?
O3 C10 C11 C12 179.1(2) . . . . ?
O3 C10 C11 C16 -0.9(3) . . . . ?
O4 C10 C11 C12 -1.6(5) . . . . ?
O4 C10 C11 C16 178.5(3) . . . . ?
N1 C1 C2 C3 -17.0(3) . . . . ?
N1 C1 C2 C8 168.1(2) . . . . ?
N1 C9 C16 C11 -123.4(2) . . . . ?
N1 C9 C16 C15 58.4(4) . . . . ?
C1 N1 C4 O1 53.5(3) . . . . ?
C1 N1 C9 O3 97.4(2) . . . . ?
C1 N1 C9 C16 -145.1(2) . . . . ?
C1 C2 C3 O1 8.3(3) . . . . ?
C1 C2 C3 C5 -170.5(2) . . . . ?
C1 C2 C8 Cl1 -7.6(3) . . . . ?
C1 C2 C8 C7 173.0(2) . . . . ?
C2 C3 C5 C6 -3.9(4) . . . . ?
C3 O1 C4 N1 -60.1(2) . . . . ?
C3 C2 C8 Cl1 177.32(18) . . . . ?
C3 C2 C8 C7 -2.1(3) . . . . ?
C3 C5 C6 C7 0.2(4) . . . . ?
C4 O1 C3 C2 31.0(3) . . . . ?
C4 O1 C3 C5 -150.2(2) . . . . ?
C4 N1 C1 O2 169.6(2) . . . . ?
C4 N1 C1 C2 -14.3(3) . . . . ?
C4 N1 C9 O3 -63.3(3) . . . . ?
C4 N1 C9 C16 54.2(3) . . . . ?
C5 C6 C7 C8 2.4(4) . . . . ?
C6 C7 C8 Cl1 179.2(2) . . . . ?
C6 C7 C8 C2 -1.4(4) . . . . ?
C8 C2 C3 O1 -176.5(2) . . . . ?
C8 C2 C3 C5 4.8(4) . . . . ?
C9 O3 C10 O4 179.7(2) . . . . ?
C9 O3 C10 C11 -0.9(3) . . . . ?
C9 N1 C1 O2 8.5(3) . . . . ?
C9 N1 C1 C2 -175.40(19) . . . . ?
C9 N1 C4 O1 -145.6(2) . . . . ?
C10 O3 C9 N1 127.1(2) . . . . ?
C10 O3 C9 C16 2.1(2) . . . . ?
C10 C11 C12 C13 -179.4(2) . . . . ?
C10 C11 C16 C9 2.2(3) . . . . ?
C10 C11 C16 C15 -179.3(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C11 C16 C9 -177.8(2) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C16 1.8(4) . . . . ?
C14 C15 C16 C9 176.3(2) . . . . ?
C14 C15 C16 C11 -1.9(4) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?

_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_rd715_3
_database_code_depnum_ccdc_archive 'CCDC 2494464'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-09-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424ae for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
alex@xrlab.ineos.ac.ru
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 F3 N O4'
_chemical_formula_sum            'C17 H10 F3 N O4'
_chemical_formula_weight         349.26
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1934(9)
_cell_length_b                   7.7898(8)
_cell_length_c                   23.076(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.820(3)
_cell_angle_gamma                90
_cell_volume                     1462.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7912
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0412 after correction.
The Ratio of minimum to maximum transmission is 0.9119.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.994
_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       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19694
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_min         2.762
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3459
_reflns_number_total             4447
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.316
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0346
_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)+(0.0472P)²+0.1749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0960
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.55964(8) 0.14727(10) 0.46862(3) 0.03706(18) Uani 1 1 d . . . . .
F2 F 0.77733(8) 0.11311(9) 0.52990(3) 0.03702(18) Uani 1 1 d . . . . .
F3 F 0.56861(8) 0.24685(10) 0.55598(3) 0.03698(18) Uani 1 1 d . . . . .
O1 O 0.78381(9) 0.21800(12) 0.29135(3) 0.0317(2) Uani 1 1 d . . . . .
H1 H 0.723950 0.200764 0.259738 0.047 Uiso 1 1 calc R U . . .
O2 O 0.44259(10) 0.66540(12) 0.30457(3) 0.0355(2) Uani 1 1 d . . . . .
O3 O 0.90996(9) 0.57728(11) 0.36935(3) 0.02972(18) Uani 1 1 d . . . . .
O4 O 0.85159(9) 0.13018(10) 0.40543(3) 0.02894(18) Uani 1 1 d . . . . .
N1 N 0.66012(10) 0.47636(13) 0.31961(4) 0.0285(2) Uani 1 1 d . . . . .
C1 C 0.69096(12) 0.29353(15) 0.33126(4) 0.0264(2) Uani 1 1 d . . . . .
C2 C 0.51698(12) 0.22550(16) 0.33111(4) 0.0275(2) Uani 1 1 d . . . . .
C3 C 0.46565(13) 0.05975(17) 0.33944(4) 0.0308(2) Uani 1 1 d . . . . .
H3 H 0.542266 -0.031721 0.346088 0.037 Uiso 1 1 calc R U . . .
C4 C 0.29669(13) 0.03121(18) 0.33774(4) 0.0335(3) Uani 1 1 d . . . . .
H4 H 0.257639 -0.081903 0.342967 0.040 Uiso 1 1 calc R U . . .
C5 C 0.18452(13) 0.16582(19) 0.32850(4) 0.0358(3) Uani 1 1 d . . . . .
H5 H 0.070415 0.143433 0.328100 0.043 Uiso 1 1 calc R U . . .
C6 C 0.23744(13) 0.33224(18) 0.31988(4) 0.0335(3) Uani 1 1 d . . . . .
H6 H 0.161432 0.424265 0.313255 0.040 Uiso 1 1 calc R U . . .
C7 C 0.40563(12) 0.35943(16) 0.32128(4) 0.0289(2) Uani 1 1 d . . . . .
C8 C 0.49685(12) 0.51994(16) 0.31407(4) 0.0294(2) Uani 1 1 d . . . . .
C9 C 0.79195(14) 0.59698(17) 0.31861(4) 0.0329(3) Uani 1 1 d . . . . .
H9A H 0.747363 0.715213 0.317338 0.039 Uiso 1 1 calc R U . . .
H9B H 0.846475 0.578709 0.283054 0.039 Uiso 1 1 calc R U . . .
C10 C 0.78372(11) 0.26463(14) 0.39341(4) 0.0243(2) Uani 1 1 d . . . . .
C11 C 0.77858(11) 0.40925(14) 0.43649(4) 0.0234(2) Uani 1 1 d . . . . .
C12 C 0.84250(12) 0.56663(15) 0.42170(4) 0.0257(2) Uani 1 1 d . . . . .
C13 C 0.85328(12) 0.70558(15) 0.45933(5) 0.0287(2) Uani 1 1 d . . . . .
H13 H 0.896163 0.812213 0.448078 0.034 Uiso 1 1 calc R U . . .
C14 C 0.80010(13) 0.68584(16) 0.51386(5) 0.0310(2) Uani 1 1 d . . . . .
H14 H 0.807582 0.779512 0.540407 0.037 Uiso 1 1 calc R U . . .
C15 C 0.73628(13) 0.53077(16) 0.52984(4) 0.0287(2) Uani 1 1 d . . . . .
H15 H 0.699831 0.519119 0.567219 0.034 Uiso 1 1 calc R U . . .
C16 C 0.72496(12) 0.39207(14) 0.49183(4) 0.0244(2) Uani 1 1 d . . . . .
C17 C 0.65793(13) 0.22513(16) 0.51132(4) 0.0285(2) Uani 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
F1 C17 1.3411(12) . ?
F2 C17 1.3427(13) . ?
F3 C17 1.3437(12) . ?
O1 H1 0.8400 . ?
O1 C1 1.3926(12) . ?
O2 C8 1.2274(15) . ?
O3 C9 1.4354(12) . ?
O3 C12 1.3894(12) . ?
O4 C10 1.2027(13) . ?
N1 C1 1.4657(16) . ?
N1 C8 1.3713(13) . ?
N1 C9 1.4339(16) . ?
C1 C2 1.5205(15) . ?
C1 C10 1.5577(13) . ?
C2 C3 1.3784(18) . ?
C2 C7 1.3868(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3980(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3939(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3887(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3908(15) . ?
C7 C8 1.4762(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5062(14) . ?
C11 C12 1.3915(16) . ?
C11 C16 1.4053(13) . ?
C12 C13 1.3838(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3883(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3836(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3878(15) . ?
C16 C17 1.5012(16) . ?

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
C1 O1 H1 109.5 . . ?
C12 O3 C9 114.62(8) . . ?
C8 N1 C1 113.75(9) . . ?
C8 N1 C9 124.38(10) . . ?
C9 N1 C1 121.73(8) . . ?
O1 C1 N1 112.65(9) . . ?
O1 C1 C2 115.91(9) . . ?
O1 C1 C10 107.63(8) . . ?
N1 C1 C2 101.37(8) . . ?
N1 C1 C10 111.34(8) . . ?
C2 C1 C10 107.84(8) . . ?
C3 C2 C1 128.88(10) . . ?
C3 C2 C7 121.45(10) . . ?
C7 C2 C1 109.67(10) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.55(11) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.15(12) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.84(10) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.66(11) . . ?
C7 C6 H6 121.2 . . ?
C2 C7 C6 121.33(12) . . ?
C2 C7 C8 108.88(9) . . ?
C6 C7 C8 129.78(11) . . ?
O2 C8 N1 125.02(11) . . ?
O2 C8 C7 128.65(10) . . ?
N1 C8 C7 106.33(10) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
N1 C9 O3 110.65(9) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O4 C10 C1 119.99(9) . . ?
O4 C10 C11 123.20(9) . . ?
C11 C10 C1 116.79(9) . . ?
C12 C11 C10 117.15(9) . . ?
C12 C11 C16 118.30(9) . . ?
C16 C11 C10 124.38(10) . . ?
O3 C12 C11 117.77(9) . . ?
C13 C12 O3 119.77(10) . . ?
C13 C12 C11 122.22(9) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.59(11) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.50(10) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.68(10) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C17 121.31(9) . . ?
C15 C16 C11 119.71(10) . . ?
C15 C16 C17 118.97(9) . . ?
F1 C17 F2 106.97(9) . . ?
F1 C17 F3 106.63(8) . . ?
F1 C17 C16 112.39(8) . . ?
F2 C17 F3 106.23(8) . . ?
F2 C17 C16 112.34(8) . . ?
F3 C17 C16 111.88(9) . . ?

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
O1 H1 O2 0.84 1.91 2.7445(10) 170.3 2_645 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
O1 C1 C2 C3 57.32(14) . . . . ?
O1 C1 C2 C7 -123.13(10) . . . . ?
O1 C1 C10 O4 -39.09(13) . . . . ?
O1 C1 C10 C11 142.64(9) . . . . ?
O3 C12 C13 C14 -173.48(9) . . . . ?
O4 C10 C11 C12 122.20(11) . . . . ?
O4 C10 C11 C16 -52.98(14) . . . . ?
N1 C1 C2 C3 179.61(9) . . . . ?
N1 C1 C2 C7 -0.83(10) . . . . ?
N1 C1 C10 O4 -163.00(9) . . . . ?
N1 C1 C10 C11 18.72(12) . . . . ?
C1 N1 C8 O2 179.63(9) . . . . ?
C1 N1 C8 C7 -0.85(11) . . . . ?
C1 N1 C9 O3 -48.86(13) . . . . ?
C1 C2 C3 C4 179.38(9) . . . . ?
C1 C2 C7 C6 -179.06(9) . . . . ?
C1 C2 C7 C8 0.40(10) . . . . ?
C1 C10 C11 C12 -59.59(12) . . . . ?
C1 C10 C11 C16 125.23(10) . . . . ?
C2 C1 C10 O4 86.63(11) . . . . ?
C2 C1 C10 C11 -91.64(11) . . . . ?
C2 C3 C4 C5 -0.59(15) . . . . ?
C2 C7 C8 O2 179.75(10) . . . . ?
C2 C7 C8 N1 0.25(10) . . . . ?
C3 C2 C7 C6 0.53(15) . . . . ?
C3 C2 C7 C8 179.99(9) . . . . ?
C3 C4 C5 C6 0.92(16) . . . . ?
C4 C5 C6 C7 -0.51(15) . . . . ?
C5 C6 C7 C2 -0.20(14) . . . . ?
C5 C6 C7 C8 -179.54(9) . . . . ?
C6 C7 C8 O2 -0.85(17) . . . . ?
C6 C7 C8 N1 179.65(9) . . . . ?
C7 C2 C3 C4 -0.13(14) . . . . ?
C8 N1 C1 O1 125.56(9) . . . . ?
C8 N1 C1 C2 1.04(10) . . . . ?
C8 N1 C1 C10 -113.42(9) . . . . ?
C8 N1 C9 O3 126.42(10) . . . . ?
C9 O3 C12 C11 80.21(12) . . . . ?
C9 O3 C12 C13 -105.28(11) . . . . ?
C9 N1 C1 O1 -58.69(11) . . . . ?
C9 N1 C1 C2 176.79(8) . . . . ?
C9 N1 C1 C10 62.33(11) . . . . ?
C9 N1 C8 O2 4.01(15) . . . . ?
C9 N1 C8 C7 -176.47(8) . . . . ?
C10 C1 C2 C3 -63.35(13) . . . . ?
C10 C1 C2 C7 116.21(9) . . . . ?
C10 C11 C12 O3 -1.71(13) . . . . ?
C10 C11 C12 C13 -176.07(8) . . . . ?
C10 C11 C16 C15 175.37(9) . . . . ?
C10 C11 C16 C17 -3.56(14) . . . . ?
C11 C12 C13 C14 0.77(15) . . . . ?
C11 C16 C17 F1 -40.90(13) . . . . ?
C11 C16 C17 F2 79.80(11) . . . . ?
C11 C16 C17 F3 -160.83(8) . . . . ?
C12 O3 C9 N1 -47.18(13) . . . . ?
C12 C11 C16 C15 0.24(14) . . . . ?
C12 C11 C16 C17 -178.69(9) . . . . ?
C12 C13 C14 C15 -0.62(15) . . . . ?
C13 C14 C15 C16 0.30(16) . . . . ?
C14 C15 C16 C11 -0.11(15) . . . . ?
C14 C15 C16 C17 178.85(9) . . . . ?
C15 C16 C17 F1 140.16(10) . . . . ?
C15 C16 C17 F2 -99.14(11) . . . . ?
C15 C16 C17 F3 20.23(13) . . . . ?
C16 C11 C12 O3 173.78(8) . . . . ?
C16 C11 C12 C13 -0.59(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
