# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2055469'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2021-01-12 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 Cl2 F N2 O4'
_chemical_formula_sum            'C18 H15 Cl2 F N2 O4'
_chemical_formula_weight         413.22
_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'
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                   16.9185(10)
_cell_length_b                   9.5036(6)
_cell_length_c                   18.6989(12)
_cell_angle_alpha                90
_cell_angle_beta                 143.5989(10)
_cell_angle_gamma                90
_cell_volume                     1784.18(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7263
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0815 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.8744.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21687
_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         29.000
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_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                   ?
_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                4068
_reflns_number_total             4745
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.058
_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)+(0.0346P)²+1.1328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0885
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.88922(8) 0.50884(10) 0.51256(7) 0.02199(19) Uani 1 1 d . . . . .
Cl1 Cl 0.71116(4) 0.59021(4) 0.01984(3) 0.02104(9) Uani 1 1 d . . . . .
Cl2 Cl 1.04426(4) 0.38866(5) 0.94216(3) 0.03136(11) Uani 1 1 d . . . . .
N1 N 0.55317(11) 0.61988(13) 0.25825(11) 0.0184(2) Uani 1 1 d . . . . .
H1 H 0.5014 0.5538 0.1990 0.022 Uiso 1 1 d R U . . .
N2 N 0.74574(13) 0.36075(14) 0.34829(12) 0.0220(3) Uani 1 1 d . . . . .
O1 O 0.63121(11) 0.32874(12) 0.24802(10) 0.0253(2) Uani 1 1 d . . . . .
O2 O 0.84642(13) 0.30422(14) 0.39996(13) 0.0397(3) Uani 1 1 d . . . . .
O3 O 0.34984(11) 0.49400(16) 0.18716(11) 0.0359(3) Uani 1 1 d . . . . .
O4 O 0.45857(10) 0.53385(12) 0.36946(9) 0.0226(2) Uani 1 1 d . . . . .
C1 C 0.68615(13) 0.61772(15) 0.32315(13) 0.0173(3) Uani 1 1 d . . . . .
H1A H 0.7346 0.7019 0.3773 0.021 Uiso 1 1 calc R U . . .
C2 C 0.75583(13) 0.48577(15) 0.40624(12) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.68076(13) 0.45170(15) 0.42208(13) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.6312 0.3613 0.3794 0.021 Uiso 1 1 calc R U . . .
C4 C 0.57674(13) 0.57513(15) 0.34924(13) 0.0176(3) Uani 1 1 d . . . . .
H4 H 0.6158 0.6554 0.4052 0.021 Uiso 1 1 calc R U . . .
C5 C 0.69117(14) 0.62705(15) 0.24617(13) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.81408(14) 0.61090(16) 0.30097(13) 0.0209(3) Uani 1 1 d . . . . .
H6 H 0.8934 0.6046 0.3862 0.025 Uiso 1 1 calc R U . . .
C7 C 0.82117(14) 0.60407(16) 0.23211(14) 0.0208(3) Uani 1 1 d . . . . .
H7 H 0.9044 0.5909 0.2694 0.025 Uiso 1 1 calc R U . . .
C8 C 0.70439(14) 0.61684(15) 0.10741(13) 0.0183(3) Uani 1 1 d . . . . .
C9 C 0.58312(14) 0.64471(16) 0.05176(13) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.5056 0.6611 -0.0326 0.024 Uiso 1 1 calc R U . . .
C10 C 0.57706(14) 0.64821(15) 0.12166(13) 0.0197(3) Uani 1 1 d . . . . .
H10 H 0.4942 0.6652 0.0842 0.024 Uiso 1 1 calc R U . . .
C11 C 0.77222(13) 0.43600(15) 0.55249(13) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.84228(14) 0.55095(16) 0.63107(13) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.8318 0.6409 0.6020 0.023 Uiso 1 1 calc R U . . .
C13 C 0.92689(14) 0.53581(16) 0.75092(13) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.9742 0.6146 0.8036 0.025 Uiso 1 1 calc R U . . .
C14 C 0.94162(14) 0.40410(17) 0.79306(13) 0.0218(3) Uani 1 1 d . . . . .
C15 C 0.87491(15) 0.28773(17) 0.71789(15) 0.0249(3) Uani 1 1 d . . . . .
H15 H 0.8863 0.1980 0.7477 0.030 Uiso 1 1 calc R U . . .
C16 C 0.79059(15) 0.30415(16) 0.59762(14) 0.0221(3) Uani 1 1 d . . . . .
H16 H 0.7451 0.2246 0.5458 0.027 Uiso 1 1 calc R U . . .
C17 C 0.44727(14) 0.52990(16) 0.29031(13) 0.0202(3) Uani 1 1 d . . . . .
C18 C 0.33611(15) 0.50897(18) 0.31979(15) 0.0255(3) Uani 1 1 d . . . . .
H18A H 0.3542 0.5142 0.3844 0.038 Uiso 1 1 calc R U . . .
H18B H 0.3014 0.4154 0.2827 0.038 Uiso 1 1 calc R U . . .
H18C H 0.2701 0.5805 0.2587 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.3679(15) . ?
Cl1 C8 1.7493(15) . ?
Cl2 C14 1.7368(16) . ?
N1 H1 0.9096 . ?
N1 C1 1.4628(17) . ?
N1 C4 1.4638(19) . ?
N2 O1 1.2306(17) . ?
N2 O2 1.2142(17) . ?
N2 C2 1.5222(19) . ?
O3 C17 1.1982(19) . ?
O4 C17 1.3316(18) . ?
O4 C18 1.4537(17) . ?
C1 H1A 1.0000 . ?
C1 C2 1.558(2) . ?
C1 C5 1.511(2) . ?
C2 C3 1.553(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.5715(19) . ?
C3 C11 1.513(2) . ?
C4 H4 1.0000 . ?
C4 C17 1.5203(19) . ?
C5 C6 1.403(2) . ?
C5 C10 1.397(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(2) . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(2) . ?
C11 C16 1.399(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(2) . ?
C14 C15 1.385(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.397(2) . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 109.3 . . ?
C1 N1 C4 103.50(11) . . ?
C4 N1 H1 108.1 . . ?
O1 N2 C2 114.48(11) . . ?
O2 N2 O1 125.67(14) . . ?
O2 N2 C2 119.82(13) . . ?
C17 O4 C18 115.44(12) . . ?
N1 C1 H1A 106.8 . . ?
N1 C1 C2 105.23(11) . . ?
N1 C1 C5 115.91(12) . . ?
C2 C1 H1A 106.8 . . ?
C5 C1 H1A 106.8 . . ?
C5 C1 C2 114.80(12) . . ?
F1 C2 N2 105.56(11) . . ?
F1 C2 C1 111.05(11) . . ?
F1 C2 C3 113.71(12) . . ?
N2 C2 C1 110.92(11) . . ?
N2 C2 C3 109.44(11) . . ?
C3 C2 C1 106.23(11) . . ?
C2 C3 H3 108.4 . . ?
C2 C3 C4 101.33(11) . . ?
C4 C3 H3 108.4 . . ?
C11 C3 C2 113.30(11) . . ?
C11 C3 H3 108.4 . . ?
C11 C3 C4 116.72(12) . . ?
N1 C4 C3 106.95(11) . . ?
N1 C4 H4 109.1 . . ?
N1 C4 C17 110.74(11) . . ?
C3 C4 H4 109.1 . . ?
C17 C4 C3 111.86(12) . . ?
C17 C4 H4 109.1 . . ?
C6 C5 C1 118.98(13) . . ?
C10 C5 C1 122.28(13) . . ?
C10 C5 C6 118.72(14) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.79(14) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 118.94(13) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 Cl1 118.76(11) . . ?
C9 C8 Cl1 119.79(11) . . ?
C9 C8 C7 121.40(14) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.85(13) . . ?
C10 C9 H9 120.6 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.95(13) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C3 121.27(13) . . ?
C12 C11 C16 118.51(14) . . ?
C16 C11 C3 120.21(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.07(14) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.31(14) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 Cl2 118.51(12) . . ?
C15 C14 Cl2 120.45(12) . . ?
C15 C14 C13 121.04(14) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.11(14) . . ?
C16 C15 H15 120.4 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.95(14) . . ?
C15 C16 H16 119.5 . . ?
O3 C17 O4 125.31(14) . . ?
O3 C17 C4 124.06(14) . . ?
O4 C17 C4 110.63(12) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 119.91(12) . . . . ?
F1 C2 C3 C11 -5.93(17) . . . . ?
Cl1 C8 C9 C10 172.10(11) . . . . ?
Cl2 C14 C15 C16 178.50(11) . . . . ?
N1 C1 C2 F1 -145.92(11) . . . . ?
N1 C1 C2 N2 97.03(13) . . . . ?
N1 C1 C2 C3 -21.81(14) . . . . ?
N1 C1 C5 C6 -173.45(13) . . . . ?
N1 C1 C5 C10 5.1(2) . . . . ?
N1 C4 C17 O3 21.4(2) . . . . ?
N1 C4 C17 O4 -159.56(12) . . . . ?
N2 C2 C3 C4 -122.34(12) . . . . ?
N2 C2 C3 C11 111.82(13) . . . . ?
O1 N2 C2 F1 -176.97(12) . . . . ?
O1 N2 C2 C1 -56.60(16) . . . . ?
O1 N2 C2 C3 60.28(16) . . . . ?
O2 N2 C2 F1 1.09(19) . . . . ?
O2 N2 C2 C1 121.46(15) . . . . ?
O2 N2 C2 C3 -121.66(15) . . . . ?
C1 N1 C4 C3 -41.25(14) . . . . ?
C1 N1 C4 C17 -163.35(11) . . . . ?
C1 C2 C3 C4 -2.53(13) . . . . ?
C1 C2 C3 C11 -128.38(12) . . . . ?
C1 C5 C6 C7 173.24(14) . . . . ?
C1 C5 C10 C9 -174.62(13) . . . . ?
C2 C1 C5 C6 -50.35(18) . . . . ?
C2 C1 C5 C10 128.24(14) . . . . ?
C2 C3 C4 N1 26.39(13) . . . . ?
C2 C3 C4 C17 147.79(12) . . . . ?
C2 C3 C11 C12 67.58(17) . . . . ?
C2 C3 C11 C16 -110.97(15) . . . . ?
C3 C4 C17 O3 -97.78(18) . . . . ?
C3 C4 C17 O4 81.25(15) . . . . ?
C3 C11 C12 C13 -179.50(13) . . . . ?
C3 C11 C16 C15 179.86(13) . . . . ?
C4 N1 C1 C2 38.55(13) . . . . ?
C4 N1 C1 C5 166.54(12) . . . . ?
C4 C3 C11 C12 -49.57(18) . . . . ?
C4 C3 C11 C16 131.88(14) . . . . ?
C5 C1 C2 F1 85.43(14) . . . . ?
C5 C1 C2 N2 -31.63(16) . . . . ?
C5 C1 C2 C3 -150.46(12) . . . . ?
C5 C6 C7 C8 1.5(2) . . . . ?
C6 C5 C10 C9 4.0(2) . . . . ?
C6 C7 C8 Cl1 -173.52(12) . . . . ?
C6 C7 C8 C9 4.0(2) . . . . ?
C7 C8 C9 C10 -5.4(2) . . . . ?
C8 C9 C10 C5 1.3(2) . . . . ?
C10 C5 C6 C7 -5.4(2) . . . . ?
C11 C3 C4 N1 149.93(12) . . . . ?
C11 C3 C4 C17 -88.67(15) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C11 C16 C15 1.3(2) . . . . ?
C12 C13 C14 Cl2 -178.18(11) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C15 C16 C11 -0.5(2) . . . . ?
C16 C11 C12 C13 -0.9(2) . . . . ?
C18 O4 C17 O3 -8.1(2) . . . . ?
C18 O4 C17 C4 172.93(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
