# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_exp_481
_database_code_depnum_ccdc_archive 'CCDC 1939935'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2019-07-11 deposited with the CCDC.	2019-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 Cl F3 N3 O4'
_chemical_formula_sum            'C21 H17 Cl F3 N3 O4'
_chemical_formula_weight         467.83

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   14.1874(8)
_cell_length_b                   8.4578(6)
_cell_length_c                   17.2415(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.519(5)
_cell_angle_gamma                90.00
_cell_volume                     2059.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2863
_cell_measurement_theta_min      3.7250
_cell_measurement_theta_max      29.9230

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_min  0.67922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12484
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         30.83
_reflns_number_total             5568
_reflns_number_gt                3478
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1100P)²+0.1100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5568
_refine_ls_number_parameters     321
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.2107
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.065
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.98845(5) 0.37800(9) 0.17204(4) 0.0603(2) Uani 1 1 d . . .
N1 N 0.91867(14) 0.9619(3) 0.08043(12) 0.0406(5) Uani 1 1 d . A .
F1 F 0.65553(16) 0.8256(3) -0.23995(10) 0.0848(7) Uani 1 1 d . . .
C1 C 0.7091(2) 0.6990(4) -0.22335(15) 0.0580(7) Uani 1 1 d . A .
N2 N 0.58549(17) 0.6537(3) -0.07774(14) 0.0565(6) Uani 1 1 d . . .
C2 C 0.74221(18) 0.6894(3) -0.13559(13) 0.0410(5) Uani 1 1 d . . .
F2 F 0.78570(15) 0.7156(3) -0.26234(10) 0.0801(6) Uani 1 1 d . . .
O3 O 0.88408(11) 0.9494(2) -0.05215(10) 0.0418(4) Uani 1 1 d . A .
C3 C 0.67885(16) 0.7457(3) -0.07333(13) 0.0383(5) Uani 1 1 d . A .
N3 N 0.68188(13) 0.9786(2) 0.00414(12) 0.0400(5) Uani 1 1 d . A .
F3 F 0.66448(17) 0.5733(3) -0.25306(10) 0.0855(7) Uani 1 1 d . . .
O4 O 0.77172(14) 0.5298(2) -0.12480(9) 0.0475(4) Uani 1 1 d . A .
C4 C 0.73173(15) 0.7169(3) 0.00805(12) 0.0348(5) Uani 1 1 d . . .
C5 C 0.80687(15) 0.5897(3) 0.01171(13) 0.0338(5) Uani 1 1 d . A .
C6 C 0.85853(16) 0.5486(3) 0.08240(13) 0.0384(5) Uani 1 1 d . . .
H6A H 0.8497 0.6044 0.1276 0.046 Uiso 1 1 calc R A .
C7 C 0.92261(17) 0.4248(3) 0.08468(14) 0.0410(5) Uani 1 1 d . A .
C8 C 0.93689(18) 0.3392(3) 0.01856(15) 0.0433(5) Uani 1 1 d . . .
H8A H 0.9805 0.2568 0.0211 0.052 Uiso 1 1 calc R A .
C9 C 0.88650(18) 0.3765(3) -0.05067(15) 0.0434(6) Uani 1 1 d . A .
H9A H 0.8952 0.3189 -0.0954 0.052 Uiso 1 1 calc R . .
C10 C 0.82175(16) 0.5016(3) -0.05381(13) 0.0374(5) Uani 1 1 d . . .
C11 C 0.65829(18) 0.9274(3) -0.07679(14) 0.0445(6) Uani 1 1 d . . .
H11A H 0.7034 0.9768 -0.1090 0.053 Uiso 1 1 calc R A .
C12 C 0.5587(2) 0.9801(4) -0.10770(18) 0.0647(8) Uani 1 1 d . A .
H12A H 0.5585 1.0921 -0.1167 0.097 Uiso 1 1 calc R . .
H12B H 0.5152 0.9551 -0.0702 0.097 Uiso 1 1 calc R . .
H12C H 0.5399 0.9262 -0.1557 0.097 Uiso 1 1 calc R . .
C13 C 0.86134(16) 0.9352(3) 0.01484(13) 0.0354(5) Uani 1 1 d . . .
C14 C 0.76171(15) 0.8845(3) 0.03819(13) 0.0346(5) Uani 1 1 d . A .
C15 C 0.77771(16) 0.8953(3) 0.12561(14) 0.0388(5) Uani 1 1 d . . .
C16 C 0.71751(19) 0.8600(3) 0.18221(15) 0.0496(6) Uani 1 1 d . A .
H16A H 0.6548 0.8316 0.1683 0.059 Uiso 1 1 calc R . .
C17 C 0.7530(2) 0.8680(4) 0.26001(17) 0.0611(8) Uani 1 1 d . . .
H17A H 0.7138 0.8429 0.2985 0.073 Uiso 1 1 calc R A .
C18 C 0.8450(2) 0.9124(4) 0.28102(16) 0.0628(8) Uani 1 1 d . A .
H18A H 0.8670 0.9176 0.3335 0.075 Uiso 1 1 calc R . .
C19 C 0.9064(2) 0.9502(4) 0.22470(16) 0.0542(7) Uani 1 1 d . . .
H19A H 0.9685 0.9819 0.2387 0.065 Uiso 1 1 calc R A .
C20 C 0.87067(17) 0.9384(3) 0.14795(14) 0.0396(5) Uani 1 1 d . A .
C21 C 0.6917(2) 1.1499(3) 0.0144(2) 0.0593(8) Uani 1 1 d . . .
H21A H 0.7140 1.1728 0.0675 0.089 Uiso 1 1 calc R A .
H21B H 0.6313 1.1996 0.0018 0.089 Uiso 1 1 calc R . .
H21C H 0.7361 1.1897 -0.0194 0.089 Uiso 1 1 calc R . .
H2 H 0.7993(18) 0.758(3) -0.1258(13) 0.034(6) Uiso 1 1 d . . .
H4 H 0.6825(19) 0.681(3) 0.0385(15) 0.039(6) Uiso 1 1 d . . .
H1 H 0.979(2) 0.990(3) 0.0813(18) 0.060(9) Uiso 1 1 d . . .
O1 O 0.53766(17) 0.6640(4) -0.02237(17) 0.0694(7) Uani 0.85 1 d P A 1
O2 O 0.5629(3) 0.5730(7) -0.1346(3) 0.1048(17) Uani 0.85 1 d P A 1
O1A O 0.595(2) 0.527(4) -0.0363(17) 0.140(9) Uani 0.15 1 d PU A 2
O2A O 0.5440(17) 0.661(3) -0.1358(14) 0.074(6) Uani 0.15 1 d PU A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.740(2) . ?
N1 C13 1.347(3) . ?
N1 C20 1.418(3) . ?
N1 H1 0.89(3) . ?
F1 C1 1.328(3) . ?
C1 F3 1.316(4) . ?
C1 F2 1.339(3) . ?
C1 C2 1.543(3) . ?
N2 O2A 1.11(2) . ?
N2 O2 1.213(5) . ?
N2 O1 1.226(3) . ?
N2 O1A 1.29(3) . ?
N2 C3 1.532(3) . ?
C2 O4 1.420(3) . ?
C2 C3 1.541(3) . ?
C2 H2 1.00(3) . ?
O3 C13 1.235(3) . ?
C3 C4 1.546(3) . ?
C3 C11 1.564(4) . ?
N3 C14 1.460(3) . ?
N3 C21 1.465(4) . ?
N3 C11 1.468(3) . ?
O4 C10 1.375(3) . ?
C4 C5 1.511(3) . ?
C4 C14 1.556(3) . ?
C4 H4 0.96(3) . ?
C5 C10 1.386(3) . ?
C5 C6 1.404(3) . ?
C6 C7 1.385(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.382(4) . ?
C8 C9 1.368(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.399(3) . ?
C9 H9A 0.9300 . ?
C11 C12 1.527(3) . ?
C11 H11A 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.566(3) . ?
C14 C15 1.505(3) . ?
C15 C20 1.387(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.388(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.373(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.402(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.374(4) . ?
C19 H19A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C13 N1 C20 111.52(19) . . ?
C13 N1 H1 124(2) . . ?
C20 N1 H1 124(2) . . ?
F3 C1 F1 108.9(3) . . ?
F3 C1 F2 105.8(2) . . ?
F1 C1 F2 106.4(3) . . ?
F3 C1 C2 115.4(2) . . ?
F1 C1 C2 111.6(2) . . ?
F2 C1 C2 108.2(2) . . ?
O2A N2 O2 39.4(11) . . ?
O2A N2 O1 114.3(14) . . ?
O2 N2 O1 123.1(3) . . ?
O2A N2 O1A 124.1(17) . . ?
O2 N2 O1A 89.2(14) . . ?
O1 N2 O1A 70.3(14) . . ?
O2A N2 C3 113.4(13) . . ?
O2 N2 C3 119.1(3) . . ?
O1 N2 C3 117.7(2) . . ?
O1A N2 C3 110.7(12) . . ?
O4 C2 C3 112.79(19) . . ?
O4 C2 C1 103.7(2) . . ?
C3 C2 C1 121.6(2) . . ?
O4 C2 H2 107.9(14) . . ?
C3 C2 H2 102.7(13) . . ?
C1 C2 H2 107.5(13) . . ?
N2 C3 C2 111.6(2) . . ?
N2 C3 C4 107.86(18) . . ?
C2 C3 C4 108.60(18) . . ?
N2 C3 C11 109.9(2) . . ?
C2 C3 C11 113.37(19) . . ?
C4 C3 C11 105.20(19) . . ?
C14 N3 C21 115.4(2) . . ?
C14 N3 C11 108.58(18) . . ?
C21 N3 C11 114.6(2) . . ?
C10 O4 C2 113.70(17) . . ?
C5 C4 C3 115.41(19) . . ?
C5 C4 C14 117.75(18) . . ?
C3 C4 C14 104.63(18) . . ?
C5 C4 H4 107.5(16) . . ?
C3 C4 H4 103.3(16) . . ?
C14 C4 H4 107.0(15) . . ?
C10 C5 C6 117.8(2) . . ?
C10 C5 C4 120.7(2) . . ?
C6 C5 C4 121.3(2) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 Cl1 119.07(19) . . ?
C6 C7 Cl1 119.54(19) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
O4 C10 C5 121.7(2) . . ?
O4 C10 C9 116.5(2) . . ?
C5 C10 C9 121.7(2) . . ?
N3 C11 C12 111.4(2) . . ?
N3 C11 C3 103.22(19) . . ?
C12 C11 C3 117.6(2) . . ?
N3 C11 H11A 108.1 . . ?
C12 C11 H11A 108.1 . . ?
C3 C11 H11A 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 N1 125.3(2) . . ?
O3 C13 C14 126.2(2) . . ?
N1 C13 C14 108.48(18) . . ?
N3 C14 C15 113.97(18) . . ?
N3 C14 C4 100.70(17) . . ?
C15 C14 C4 113.55(18) . . ?
N3 C14 C13 115.60(18) . . ?
C15 C14 C13 100.84(18) . . ?
C4 C14 C13 112.82(18) . . ?
C20 C15 C16 119.6(2) . . ?
C20 C15 C14 110.0(2) . . ?
C16 C15 C14 130.3(2) . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16A 120.7 . . ?
C15 C16 H16A 120.7 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C20 C19 C18 117.0(3) . . ?
C20 C19 H19A 121.5 . . ?
C18 C19 H19A 121.5 . . ?
C19 C20 C15 122.6(2) . . ?
C19 C20 N1 128.2(2) . . ?
C15 C20 N1 109.1(2) . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
F3 C1 C2 O4 37.8(3) . . . . ?
F1 C1 C2 O4 162.7(2) . . . . ?
F2 C1 C2 O4 -80.5(3) . . . . ?
F3 C1 C2 C3 -90.4(3) . . . . ?
F1 C1 C2 C3 34.5(4) . . . . ?
F2 C1 C2 C3 151.3(2) . . . . ?
O2A N2 C3 C2 -57.2(13) . . . . ?
O2 N2 C3 C2 -13.5(5) . . . . ?
O1 N2 C3 C2 165.5(3) . . . . ?
O1A N2 C3 C2 87.6(16) . . . . ?
O2A N2 C3 C4 -176.4(13) . . . . ?
O2 N2 C3 C4 -132.7(4) . . . . ?
O1 N2 C3 C4 46.3(3) . . . . ?
O1A N2 C3 C4 -31.6(16) . . . . ?
O2A N2 C3 C11 69.4(13) . . . . ?
O2 N2 C3 C11 113.1(4) . . . . ?
O1 N2 C3 C11 -67.8(3) . . . . ?
O1A N2 C3 C11 -145.8(16) . . . . ?
O4 C2 C3 N2 -64.0(3) . . . . ?
C1 C2 C3 N2 60.1(3) . . . . ?
O4 C2 C3 C4 54.8(3) . . . . ?
C1 C2 C3 C4 178.9(2) . . . . ?
O4 C2 C3 C11 171.3(2) . . . . ?
C1 C2 C3 C11 -64.6(3) . . . . ?
C3 C2 O4 C10 -58.9(3) . . . . ?
C1 C2 O4 C10 167.7(2) . . . . ?
N2 C3 C4 C5 97.5(2) . . . . ?
C2 C3 C4 C5 -23.6(3) . . . . ?
C11 C3 C4 C5 -145.26(19) . . . . ?
N2 C3 C4 C14 -131.5(2) . . . . ?
C2 C3 C4 C14 107.5(2) . . . . ?
C11 C3 C4 C14 -14.2(2) . . . . ?
C3 C4 C5 C10 -3.3(3) . . . . ?
C14 C4 C5 C10 -127.8(2) . . . . ?
C3 C4 C5 C6 -178.29(19) . . . . ?
C14 C4 C5 C6 57.2(3) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C4 C5 C6 C7 175.9(2) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 Cl1 178.36(17) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
Cl1 C7 C8 C9 -179.07(18) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C2 O4 C10 C5 28.9(3) . . . . ?
C2 O4 C10 C9 -152.8(2) . . . . ?
C6 C5 C10 O4 177.6(2) . . . . ?
C4 C5 C10 O4 2.4(3) . . . . ?
C6 C5 C10 C9 -0.6(3) . . . . ?
C4 C5 C10 C9 -175.7(2) . . . . ?
C8 C9 C10 O4 -178.3(2) . . . . ?
C8 C9 C10 C5 -0.1(4) . . . . ?
C14 N3 C11 C12 161.8(2) . . . . ?
C21 N3 C11 C12 -67.5(3) . . . . ?
C14 N3 C11 C3 34.8(2) . . . . ?
C21 N3 C11 C3 165.5(2) . . . . ?
N2 C3 C11 N3 104.9(2) . . . . ?
C2 C3 C11 N3 -129.4(2) . . . . ?
C4 C3 C11 N3 -10.9(2) . . . . ?
N2 C3 C11 C12 -18.1(3) . . . . ?
C2 C3 C11 C12 107.6(3) . . . . ?
C4 C3 C11 C12 -133.9(2) . . . . ?
C20 N1 C13 O3 178.7(2) . . . . ?
C20 N1 C13 C14 -0.9(3) . . . . ?
C21 N3 C14 C15 64.3(3) . . . . ?
C11 N3 C14 C15 -165.46(19) . . . . ?
C21 N3 C14 C4 -173.8(2) . . . . ?
C11 N3 C14 C4 -43.5(2) . . . . ?
C21 N3 C14 C13 -51.9(3) . . . . ?
C11 N3 C14 C13 78.4(2) . . . . ?
C5 C4 C14 N3 163.71(18) . . . . ?
C3 C4 C14 N3 34.0(2) . . . . ?
C5 C4 C14 C15 -74.1(2) . . . . ?
C3 C4 C14 C15 156.26(18) . . . . ?
C5 C4 C14 C13 39.9(3) . . . . ?
C3 C4 C14 C13 -89.8(2) . . . . ?
O3 C13 C14 N3 -54.5(3) . . . . ?
N1 C13 C14 N3 125.1(2) . . . . ?
O3 C13 C14 C15 -177.9(2) . . . . ?
N1 C13 C14 C15 1.7(2) . . . . ?
O3 C13 C14 C4 60.6(3) . . . . ?
N1 C13 C14 C4 -119.8(2) . . . . ?
N3 C14 C15 C20 -126.4(2) . . . . ?
C4 C14 C15 C20 119.0(2) . . . . ?
C13 C14 C15 C20 -1.9(2) . . . . ?
N3 C14 C15 C16 58.1(3) . . . . ?
C4 C14 C15 C16 -56.5(3) . . . . ?
C13 C14 C15 C16 -177.4(3) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?
C14 C15 C16 C17 174.7(3) . . . . ?
C15 C16 C17 C18 1.1(5) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C18 C19 C20 C15 1.6(4) . . . . ?
C18 C19 C20 N1 -176.6(3) . . . . ?
C16 C15 C20 C19 -0.9(4) . . . . ?
C14 C15 C20 C19 -177.0(2) . . . . ?
C16 C15 C20 N1 177.6(2) . . . . ?
C14 C15 C20 N1 1.5(3) . . . . ?
C13 N1 C20 C19 178.1(3) . . . . ?
C13 N1 C20 C15 -0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.860
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 1939936'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2019-07-11 deposited with the CCDC.	2019-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 Cl F3 N3 O4'
_chemical_formula_sum            'C21 H17 Cl F3 N3 O4'
_chemical_formula_weight         467.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.726(9)
_cell_length_b                   12.407(4)
_cell_length_c                   15.495(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.72(5)
_cell_angle_gamma                90.00
_cell_volume                     1964.2(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    11886
_cell_measurement_theta_min      3.5266
_cell_measurement_theta_max      65.2429

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    2.315
_exptl_absorpt_correction_T_min  0.84803
_exptl_absorpt_correction_T_max  1.19294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25025
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.45
_diffrn_reflns_theta_max         66.92
_reflns_number_total             3461
_reflns_number_gt                2798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1050P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3461
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.28326(6) 0.94754(5) 0.09536(4) 0.0664(2) Uani 1 1 d . . .
F1 F 0.71720(16) 0.42679(14) 0.01380(10) 0.0767(5) Uani 1 1 d . . .
N1 N 0.63144(15) 0.51139(12) 0.34200(10) 0.0374(3) Uani 1 1 d . . .
O1 O 0.65919(15) 0.62609(12) 0.06663(10) 0.0534(4) Uani 1 1 d . . .
C1 C 0.7687(2) 0.46520(17) 0.09562(13) 0.0483(5) Uani 1 1 d . . .
F2 F 0.87554(14) 0.51542(13) 0.09486(12) 0.0738(4) Uani 1 1 d . . .
N2 N 0.30756(15) 0.57854(15) 0.23294(11) 0.0449(4) Uani 1 1 d . . .
C2 C 0.67383(19) 0.53651(15) 0.12323(13) 0.0391(4) Uani 1 1 d . . .
O2 O 0.85586(18) 0.70442(14) 0.22771(19) 0.0902(7) Uani 1 1 d . . .
F3 F 0.80320(18) 0.38286(12) 0.15012(10) 0.0784(5) Uani 1 1 d . . .
C3 C 0.71107(16) 0.56513(13) 0.22373(12) 0.0339(4) Uani 1 1 d . . .
N3 N 0.84629(15) 0.61453(14) 0.25183(12) 0.0458(4) Uani 1 1 d . . .
O3 O 0.93689(16) 0.56257(18) 0.29494(15) 0.0799(6) Uani 1 1 d . . .
O4 O 0.41725(14) 0.46720(12) 0.16432(10) 0.0520(4) Uani 1 1 d . . .
C4 C 0.61628(16) 0.64982(13) 0.24021(11) 0.0320(4) Uani 1 1 d . . .
C5 C 0.54536(16) 0.71343(14) 0.15804(12) 0.0351(4) Uani 1 1 d . . .
C6 C 0.45614(18) 0.79194(14) 0.16303(12) 0.0389(4) Uani 1 1 d . . .
H6A H 0.4368 0.8029 0.2169 0.047 Uiso 1 1 calc R . .
C7 C 0.39662(19) 0.85324(15) 0.08869(14) 0.0456(4) Uani 1 1 d . . .
C8 C 0.4257(2) 0.84100(19) 0.00880(15) 0.0571(5) Uani 1 1 d . . .
H8A H 0.3859 0.8846 -0.0408 0.068 Uiso 1 1 calc R . .
C9 C 0.5138(3) 0.7641(2) 0.00322(15) 0.0601(6) Uani 1 1 d . . .
H9A H 0.5348 0.7547 -0.0503 0.072 Uiso 1 1 calc R . .
C10 C 0.57125(19) 0.70076(16) 0.07725(13) 0.0441(4) Uani 1 1 d . . .
C11 C 0.70188(19) 0.47007(15) 0.28298(13) 0.0408(4) Uani 1 1 d . . .
H11A H 0.6547 0.4108 0.2466 0.049 Uiso 1 1 calc R . .
H11B H 0.7883 0.4453 0.3178 0.049 Uiso 1 1 calc R . .
C12 C 0.41485(18) 0.53472(15) 0.22016(12) 0.0390(4) Uani 1 1 d . . .
C13 C 0.53447(16) 0.58577(14) 0.28917(11) 0.0337(4) Uani 1 1 d . . .
C14 C 0.47289(17) 0.65390(14) 0.34390(11) 0.0356(4) Uani 1 1 d . . .
C15 C 0.52692(19) 0.71591(15) 0.41841(12) 0.0422(4) Uani 1 1 d . . .
H15A H 0.6171 0.7174 0.4454 0.051 Uiso 1 1 calc R . .
C16 C 0.4454(2) 0.77646(17) 0.45310(15) 0.0517(5) Uani 1 1 d . . .
H16A H 0.4807 0.8193 0.5039 0.062 Uiso 1 1 calc R . .
C17 C 0.3135(2) 0.77369(18) 0.41313(17) 0.0564(5) Uani 1 1 d . . .
H17A H 0.2600 0.8159 0.4368 0.068 Uiso 1 1 calc R . .
C18 C 0.2573(2) 0.71043(18) 0.33909(16) 0.0529(5) Uani 1 1 d . . .
H18A H 0.1671 0.7087 0.3123 0.063 Uiso 1 1 calc R . .
C19 C 0.33915(18) 0.64985(15) 0.30599(12) 0.0395(4) Uani 1 1 d . . .
C20 C 0.1771(2) 0.5541(2) 0.17797(18) 0.0651(6) Uani 1 1 d . . .
H20A H 0.1802 0.5118 0.1268 0.098 Uiso 1 1 calc R . .
H20B H 0.1306 0.6200 0.1571 0.098 Uiso 1 1 calc R . .
H20C H 0.1329 0.5143 0.2131 0.098 Uiso 1 1 calc R . .
C21 C 0.5830(2) 0.42787(16) 0.38853(15) 0.0515(5) Uani 1 1 d . . .
H21A H 0.5417 0.4603 0.4291 0.077 Uiso 1 1 calc R . .
H21B H 0.6546 0.3836 0.4224 0.077 Uiso 1 1 calc R . .
H21C H 0.5205 0.3843 0.3450 0.077 Uiso 1 1 calc R . .
H4 H 0.6672(19) 0.7001(16) 0.2842(13) 0.031(4) Uiso 1 1 d . . .
H2 H 0.592(2) 0.4989(17) 0.1096(14) 0.039(5) 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
Cl1 C7 1.713(2) . ?
F1 C1 1.309(3) . ?
N1 C13 1.444(2) . ?
N1 C21 1.446(2) . ?
N1 C11 1.446(2) . ?
O1 C10 1.367(2) . ?
O1 C2 1.395(2) . ?
C1 F3 1.305(2) . ?
C1 F2 1.308(3) . ?
C1 C2 1.505(3) . ?
N2 C12 1.341(3) . ?
N2 C19 1.395(3) . ?
N2 C20 1.432(3) . ?
C2 C3 1.527(3) . ?
C2 H2 0.96(2) . ?
O2 N3 1.191(3) . ?
C3 N3 1.511(3) . ?
C3 C11 1.516(2) . ?
C3 C4 1.537(2) . ?
N3 O3 1.188(3) . ?
O4 C12 1.210(2) . ?
C4 C5 1.494(2) . ?
C4 C13 1.543(2) . ?
C4 H4 0.96(2) . ?
C5 C10 1.371(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.366(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(3) . ?
C8 C9 1.364(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.372(3) . ?
C9 H9A 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.535(3) . ?
C13 C14 1.487(2) . ?
C14 C15 1.361(3) . ?
C14 C19 1.376(3) . ?
C15 C16 1.380(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.361(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.369(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.368(3) . ?
C18 H18A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C13 N1 C21 115.75(16) . . ?
C13 N1 C11 107.03(14) . . ?
C21 N1 C11 113.42(15) . . ?
C10 O1 C2 114.46(14) . . ?
F3 C1 F2 107.56(19) . . ?
F3 C1 F1 107.14(19) . . ?
F2 C1 F1 106.08(18) . . ?
F3 C1 C2 111.08(16) . . ?
F2 C1 C2 113.11(18) . . ?
F1 C1 C2 111.54(18) . . ?
C12 N2 C19 111.69(16) . . ?
C12 N2 C20 123.63(18) . . ?
C19 N2 C20 124.67(18) . . ?
O1 C2 C1 104.26(15) . . ?
O1 C2 C3 113.60(15) . . ?
C1 C2 C3 115.91(16) . . ?
O1 C2 H2 109.2(13) . . ?
C1 C2 H2 107.5(13) . . ?
C3 C2 H2 106.1(13) . . ?
N3 C3 C11 112.00(15) . . ?
N3 C3 C2 108.56(15) . . ?
C11 C3 C2 113.05(15) . . ?
N3 C3 C4 107.48(14) . . ?
C11 C3 C4 105.25(14) . . ?
C2 C3 C4 110.34(14) . . ?
O3 N3 O2 123.44(19) . . ?
O3 N3 C3 119.41(18) . . ?
O2 N3 C3 117.15(17) . . ?
C5 C4 C3 114.24(14) . . ?
C5 C4 C13 118.21(15) . . ?
C3 C4 C13 103.50(13) . . ?
C5 C4 H4 107.1(11) . . ?
C3 C4 H4 107.4(11) . . ?
C13 C4 H4 105.7(11) . . ?
C10 C5 C6 117.85(16) . . ?
C10 C5 C4 121.69(16) . . ?
C6 C5 C4 120.36(16) . . ?
C7 C6 C5 119.90(18) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C6 C7 C8 121.48(18) . . ?
C6 C7 Cl1 119.19(16) . . ?
C8 C7 Cl1 119.33(16) . . ?
C9 C8 C7 119.09(19) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
O1 C10 C5 121.75(17) . . ?
O1 C10 C9 115.99(18) . . ?
C5 C10 C9 122.23(18) . . ?
N1 C11 C3 104.47(14) . . ?
N1 C11 H11A 110.9 . . ?
C3 C11 H11A 110.9 . . ?
N1 C11 H11B 110.9 . . ?
C3 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
O4 C12 N2 126.32(18) . . ?
O4 C12 C13 126.06(17) . . ?
N2 C12 C13 107.62(16) . . ?
N1 C13 C14 114.09(14) . . ?
N1 C13 C12 115.87(15) . . ?
C14 C13 C12 102.11(14) . . ?
N1 C13 C4 100.87(14) . . ?
C14 C13 C4 113.91(14) . . ?
C12 C13 C4 110.47(14) . . ?
C15 C14 C19 120.15(17) . . ?
C15 C14 C13 131.04(17) . . ?
C19 C14 C13 108.79(16) . . ?
C14 C15 C16 118.78(19) . . ?
C14 C15 H15A 120.6 . . ?
C16 C15 H15A 120.6 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C18 121.8(2) . . ?
C16 C17 H17A 119.1 . . ?
C18 C17 H17A 119.1 . . ?
C19 C18 C17 117.4(2) . . ?
C19 C18 H18A 121.3 . . ?
C17 C18 H18A 121.3 . . ?
C18 C19 C14 121.61(19) . . ?
C18 C19 N2 128.87(19) . . ?
C14 C19 N2 109.51(16) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C10 O1 C2 C1 177.23(17) . . . . ?
C10 O1 C2 C3 -55.7(2) . . . . ?
F3 C1 C2 O1 172.91(19) . . . . ?
F2 C1 C2 O1 51.8(2) . . . . ?
F1 C1 C2 O1 -67.6(2) . . . . ?
F3 C1 C2 C3 47.3(3) . . . . ?
F2 C1 C2 C3 -73.8(2) . . . . ?
F1 C1 C2 C3 166.72(17) . . . . ?
O1 C2 C3 N3 -65.88(19) . . . . ?
C1 C2 C3 N3 54.8(2) . . . . ?
O1 C2 C3 C11 169.21(15) . . . . ?
C1 C2 C3 C11 -70.1(2) . . . . ?
O1 C2 C3 C4 51.6(2) . . . . ?
C1 C2 C3 C4 172.38(15) . . . . ?
C11 C3 N3 O3 21.1(3) . . . . ?
C2 C3 N3 O3 -104.5(2) . . . . ?
C4 C3 N3 O3 136.2(2) . . . . ?
C11 C3 N3 O2 -160.1(2) . . . . ?
C2 C3 N3 O2 74.4(2) . . . . ?
C4 C3 N3 O2 -44.9(2) . . . . ?
N3 C3 C4 C5 96.80(17) . . . . ?
C11 C3 C4 C5 -143.67(15) . . . . ?
C2 C3 C4 C5 -21.4(2) . . . . ?
N3 C3 C4 C13 -133.32(14) . . . . ?
C11 C3 C4 C13 -13.79(17) . . . . ?
C2 C3 C4 C13 108.48(16) . . . . ?
C3 C4 C5 C10 -4.2(2) . . . . ?
C13 C4 C5 C10 -126.38(19) . . . . ?
C3 C4 C5 C6 179.51(15) . . . . ?
C13 C4 C5 C6 57.4(2) . . . . ?
C10 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C7 176.79(17) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C5 C6 C7 Cl1 178.27(14) . . . . ?
C6 C7 C8 C9 1.6(4) . . . . ?
Cl1 C7 C8 C9 -178.5(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C2 O1 C10 C5 27.7(3) . . . . ?
C2 O1 C10 C9 -154.2(2) . . . . ?
C6 C5 C10 O1 179.19(18) . . . . ?
C4 C5 C10 O1 2.8(3) . . . . ?
C6 C5 C10 C9 1.2(3) . . . . ?
C4 C5 C10 C9 -175.1(2) . . . . ?
C8 C9 C10 O1 -179.5(2) . . . . ?
C8 C9 C10 C5 -1.5(4) . . . . ?
C13 N1 C11 C3 36.39(18) . . . . ?
C21 N1 C11 C3 165.28(16) . . . . ?
N3 C3 C11 N1 104.23(17) . . . . ?
C2 C3 C11 N1 -132.74(16) . . . . ?
C4 C3 C11 N1 -12.25(18) . . . . ?
C19 N2 C12 O4 176.91(18) . . . . ?
C20 N2 C12 O4 -2.9(3) . . . . ?
C19 N2 C12 C13 -3.2(2) . . . . ?
C20 N2 C12 C13 177.0(2) . . . . ?
C21 N1 C13 C14 65.3(2) . . . . ?
C11 N1 C13 C14 -167.18(14) . . . . ?
C21 N1 C13 C12 -52.9(2) . . . . ?
C11 N1 C13 C12 74.64(18) . . . . ?
C21 N1 C13 C4 -172.16(15) . . . . ?
C11 N1 C13 C4 -44.63(16) . . . . ?
O4 C12 C13 N1 -50.5(2) . . . . ?
N2 C12 C13 N1 129.52(16) . . . . ?
O4 C12 C13 C14 -175.15(18) . . . . ?
N2 C12 C13 C14 4.91(18) . . . . ?
O4 C12 C13 C4 63.3(2) . . . . ?
N2 C12 C13 C4 -116.60(16) . . . . ?
C5 C4 C13 N1 162.07(14) . . . . ?
C3 C4 C13 N1 34.63(16) . . . . ?
C5 C4 C13 C14 -75.25(19) . . . . ?
C3 C4 C13 C14 157.31(14) . . . . ?
C5 C4 C13 C12 39.0(2) . . . . ?
C3 C4 C13 C12 -88.45(17) . . . . ?
N1 C13 C14 C15 50.8(2) . . . . ?
C12 C13 C14 C15 176.61(18) . . . . ?
C4 C13 C14 C15 -64.3(2) . . . . ?
N1 C13 C14 C19 -130.80(16) . . . . ?
C12 C13 C14 C19 -5.02(18) . . . . ?
C4 C13 C14 C19 114.09(16) . . . . ?
C19 C14 C15 C16 -1.9(3) . . . . ?
C13 C14 C15 C16 176.36(18) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C14 -1.6(3) . . . . ?
C17 C18 C19 N2 179.2(2) . . . . ?
C15 C14 C19 C18 2.7(3) . . . . ?
C13 C14 C19 C18 -175.90(17) . . . . ?
C15 C14 C19 N2 -177.92(16) . . . . ?
C13 C14 C19 N2 3.5(2) . . . . ?
C12 N2 C19 C18 179.21(19) . . . . ?
C20 N2 C19 C18 -1.0(3) . . . . ?
C12 N2 C19 C14 -0.1(2) . . . . ?
C20 N2 C19 C14 179.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        66.92
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_exp_1070
_database_code_depnum_ccdc_archive 'CCDC 1939937'
loop_
_audit_author_name
_audit_author_address
'Alexey Barkov'
;Ural Federal University
Russia
;
_audit_update_record             
;
2019-07-11 deposited with the CCDC.	2019-10-27 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 F3 N3 O4'
_chemical_formula_sum            'C20 H16 F3 N3 O4'
_chemical_formula_weight         419.36
_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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   29.7240(10)
_cell_length_b                   29.7240(10)
_cell_length_c                   11.0656(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     8466.9(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3411
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.1180
_cell_measurement_theta_min      2.4400
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3888
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13347
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         2.37
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9773
_diffrn_measured_fraction_theta_max 0.9593
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00  -53.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -53.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00  -10.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -82.0000   23.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920  -99.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -72.00  -40.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.7920 -178.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -47.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       23.2920  -77.0000 -150.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0024375000
_diffrn_orient_matrix_UB_12      0.0227155000
_diffrn_orient_matrix_UB_13      0.0272255000
_diffrn_orient_matrix_UB_21      0.0238802000
_diffrn_orient_matrix_UB_22      0.0153046000
_diffrn_orient_matrix_UB_23      -0.0306731000
_diffrn_orient_matrix_UB_31      -0.0135233000
_diffrn_orient_matrix_UB_32      0.0030367000
_diffrn_orient_matrix_UB_33      -0.0492693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3616
_reflns_number_total             4853
_reflns_odcompleteness_completeness 97.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1010P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1523
_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.,SQUEEZE
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38052(4) 0.44180(4) 0.34387(9) 0.0373(3) Uani 1 1 d . . .
F2 F 0.37757(4) 0.39899(4) 0.60442(11) 0.0663(3) Uani 1 1 d . . .
F3 F 0.45826(5) 0.45265(5) 0.59481(14) 0.0809(4) Uani 1 1 d . . .
O4 O 0.37039(4) 0.57833(4) 0.63982(9) 0.0465(3) Uani 1 1 d . . .
F1 F 0.42162(7) 0.39497(6) 0.45794(13) 0.0898(5) Uani 1 1 d . . .
O2 O 0.38021(6) 0.48778(5) 0.73460(10) 0.0595(4) Uani 1 1 d . . .
O3 O 0.45032(5) 0.54066(5) 0.63828(11) 0.0568(3) Uani 1 1 d . . .
N1 N 0.33373(5) 0.52029(5) 0.39529(11) 0.0366(3) Uani 1 1 d . . .
N2 N 0.43659(6) 0.62858(5) 0.51083(12) 0.0435(3) Uani 1 1 d . . .
N3 N 0.40435(5) 0.50711(5) 0.64224(11) 0.0421(3) Uani 1 1 d . . .
C3 C 0.37763(5) 0.48994(5) 0.51833(11) 0.0313(3) Uani 1 1 d . . .
C13 C 0.42944(5) 0.57029(5) 0.36614(12) 0.0331(3) Uani 1 1 d . . .
C12 C 0.38481(5) 0.54070(5) 0.45304(11) 0.0309(3) Uani 1 1 d . . .
C5 C 0.29860(5) 0.40568(5) 0.44834(12) 0.0339(3) Uani 1 1 d . . .
C11 C 0.39563(6) 0.58392(6) 0.54838(12) 0.0362(3) Uani 1 1 d . . .
C10 C 0.32901(6) 0.40276(5) 0.35779(12) 0.0342(3) Uani 1 1 d . . .
C4 C 0.31836(5) 0.45319(5) 0.52828(13) 0.0344(3) Uani 1 1 d . . .
C2 C 0.40635(5) 0.46560(6) 0.45262(13) 0.0347(3) Uani 1 1 d . . .
C18 C 0.45814(6) 0.62153(6) 0.40491(13) 0.0378(3) Uani 1 1 d . . .
C14 C 0.44226(6) 0.55588(6) 0.25845(13) 0.0388(3) Uani 1 1 d . . .
H14 H 0.4224 0.5222 0.2293 0.047 Uiso 1 1 calc R . .
C1 C 0.41572(7) 0.42763(7) 0.52754(16) 0.0489(4) Uani 1 1 d . . .
C19 C 0.29568(6) 0.48663(6) 0.48445(15) 0.0395(3) Uani 1 1 d . . .
C6 C 0.24717(6) 0.36554(6) 0.45609(15) 0.0430(4) Uani 1 1 d . . .
H6 H 0.2258 0.3661 0.5168 0.052 Uiso 1 1 calc R . .
C15 C 0.48525(7) 0.59259(7) 0.19446(13) 0.0472(4) Uani 1 1 d . . .
H15 H 0.4948 0.5831 0.1230 0.057 Uiso 1 1 calc R . .
C9 C 0.30980(7) 0.36257(6) 0.27459(15) 0.0448(4) Uani 1 1 d . . .
H9 H 0.3311 0.3619 0.2138 0.054 Uiso 1 1 calc R . .
C7 C 0.22759(7) 0.32488(6) 0.37426(17) 0.0521(4) Uani 1 1 d . . .
H7 H 0.1933 0.2982 0.3805 0.063 Uiso 1 1 calc R . .
C16 C 0.51383(7) 0.64292(7) 0.23592(16) 0.0515(4) Uani 1 1 d . . .
H16 H 0.5426 0.6669 0.1920 0.062 Uiso 1 1 calc R . .
C17 C 0.50065(7) 0.65860(6) 0.34163(14) 0.0485(4) Uani 1 1 d . . .
H17 H 0.5197 0.6927 0.3689 0.058 Uiso 1 1 calc R . .
C8 C 0.25888(7) 0.32379(7) 0.28329(17) 0.0526(4) Uani 1 1 d . . .
H8 H 0.2454 0.2967 0.2277 0.063 Uiso 1 1 calc R . .
C20 C 0.32334(8) 0.55928(7) 0.34334(19) 0.0577(5) Uani 1 1 d . . .
H20A H 0.3224 0.5809 0.4066 0.087 Uiso 1 1 calc R . .
H20B H 0.2905 0.5423 0.3023 0.087 Uiso 1 1 calc R . .
H20C H 0.3503 0.5803 0.2870 0.087 Uiso 1 1 calc R . .
H2A H 0.4393(7) 0.4912(7) 0.4305(15) 0.042(4) Uiso 1 1 d . . .
H19A H 0.2629(7) 0.4657(7) 0.4451(16) 0.043(4) Uiso 1 1 d . . .
H4 H 0.3106(7) 0.4425(6) 0.6142(15) 0.041(4) Uiso 1 1 d . . .
H19B H 0.2915(7) 0.5048(7) 0.5519(16) 0.045(5) Uiso 1 1 d . . .
H2 H 0.4494(8) 0.6572(9) 0.5533(19) 0.066(6) 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 C10 1.3921(17) . ?
O1 C2 1.4124(17) . ?
F2 C1 1.330(2) . ?
F3 C1 1.329(2) . ?
O4 C11 1.2205(17) . ?
F1 C1 1.318(2) . ?
O2 N3 1.2154(17) . ?
O3 N3 1.2251(17) . ?
N1 C12 1.4698(18) . ?
N1 C19 1.457(2) . ?
N1 C20 1.458(2) . ?
N2 C11 1.3421(19) . ?
N2 C18 1.4009(19) . ?
N2 H2 0.87(2) . ?
N3 C3 1.5381(17) . ?
C3 C12 1.5883(19) . ?
C3 C4 1.5442(19) . ?
C3 C2 1.549(2) . ?
C13 C12 1.5136(19) . ?
C13 C18 1.390(2) . ?
C13 C14 1.383(2) . ?
C12 C11 1.5663(19) . ?
C5 C10 1.381(2) . ?
C5 C4 1.514(2) . ?
C5 C6 1.394(2) . ?
C10 C9 1.385(2) . ?
C4 C19 1.532(2) . ?
C4 H4 0.993(17) . ?
C2 C1 1.534(2) . ?
C2 H2A 0.923(18) . ?
C18 C17 1.382(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(2) . ?
C19 H19A 0.959(19) . ?
C19 H19B 0.966(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.373(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9300 . ?
C8 H8 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 O1 C2 114.78(11) . . ?
C19 N1 C12 106.02(11) . . ?
C19 N1 C20 114.37(13) . . ?
C20 N1 C12 115.39(13) . . ?
C11 N2 C18 111.56(13) . . ?
C11 N2 H2 122.3(14) . . ?
C18 N2 H2 125.8(14) . . ?
O2 N3 O3 124.71(13) . . ?
O2 N3 C3 120.53(13) . . ?
O3 N3 C3 114.76(12) . . ?
N3 C3 C12 106.76(10) . . ?
N3 C3 C4 112.84(11) . . ?
N3 C3 C2 105.07(11) . . ?
C4 C3 C12 105.55(11) . . ?
C4 C3 C2 113.79(11) . . ?
C2 C3 C12 112.75(11) . . ?
C18 C13 C12 108.66(11) . . ?
C14 C13 C12 131.66(13) . . ?
C14 C13 C18 119.48(13) . . ?
N1 C12 C3 100.68(10) . . ?
N1 C12 C13 112.83(11) . . ?
N1 C12 C11 112.19(12) . . ?
C13 C12 C3 120.21(11) . . ?
C13 C12 C11 100.98(10) . . ?
C11 C12 C3 110.34(10) . . ?
C10 C5 C4 121.45(12) . . ?
C10 C5 C6 117.57(13) . . ?
C6 C5 C4 120.68(13) . . ?
O4 C11 N2 125.67(13) . . ?
O4 C11 C12 125.92(13) . . ?
N2 C11 C12 108.39(11) . . ?
C5 C10 O1 120.63(12) . . ?
C5 C10 C9 122.41(14) . . ?
C9 C10 O1 116.92(13) . . ?
C3 C4 H4 107.2(10) . . ?
C5 C4 C3 113.05(11) . . ?
C5 C4 C19 109.19(12) . . ?
C5 C4 H4 110.0(10) . . ?
C19 C4 C3 103.60(11) . . ?
C19 C4 H4 113.8(10) . . ?
O1 C2 C3 110.21(11) . . ?
O1 C2 C1 110.19(12) . . ?
O1 C2 H2A 105.9(10) . . ?
C3 C2 H2A 110.1(11) . . ?
C1 C2 C3 115.79(12) . . ?
C1 C2 H2A 104.1(11) . . ?
C13 C18 N2 110.25(12) . . ?
C17 C18 N2 127.52(14) . . ?
C17 C18 C13 122.21(14) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 118.92(14) . . ?
C15 C14 H14 120.5 . . ?
F2 C1 C2 113.98(14) . . ?
F3 C1 F2 105.55(14) . . ?
F3 C1 C2 111.28(14) . . ?
F1 C1 F2 106.70(15) . . ?
F1 C1 F3 107.44(15) . . ?
F1 C1 C2 111.47(14) . . ?
N1 C19 C4 102.57(12) . . ?
N1 C19 H19A 109.0(10) . . ?
N1 C19 H19B 114.3(11) . . ?
C4 C19 H19A 111.0(11) . . ?
C4 C19 H19B 109.9(10) . . ?
H19A C19 H19B 110.0(15) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.62(15) . . ?
C7 C6 H6 119.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.57(14) . . ?
C16 C15 H15 119.7 . . ?
C10 C9 H9 120.5 . . ?
C8 C9 C10 118.93(16) . . ?
C8 C9 H9 120.5 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.20(15) . . ?
C8 C7 H7 119.9 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.43(15) . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 117.32(15) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C9 C8 C7 120.25(15) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C9 C8 -178.63(14) . . . . ?
O1 C2 C1 F2 -90.54(16) . . . . ?
O1 C2 C1 F3 150.24(14) . . . . ?
O1 C2 C1 F1 30.31(19) . . . . ?
O2 N3 C3 C12 123.26(15) . . . . ?
O2 N3 C3 C4 7.7(2) . . . . ?
O2 N3 C3 C2 -116.78(15) . . . . ?
O3 N3 C3 C12 -56.83(16) . . . . ?
O3 N3 C3 C4 -172.35(13) . . . . ?
O3 N3 C3 C2 63.13(16) . . . . ?
N1 C12 C11 O4 61.74(19) . . . . ?
N1 C12 C11 N2 -116.60(14) . . . . ?
N2 C18 C17 C16 -177.60(17) . . . . ?
N3 C3 C12 N1 -140.53(11) . . . . ?
N3 C3 C12 C13 94.95(14) . . . . ?
N3 C3 C12 C11 -21.86(14) . . . . ?
N3 C3 C4 C5 -132.57(12) . . . . ?
N3 C3 C4 C19 109.37(13) . . . . ?
N3 C3 C2 O1 171.87(10) . . . . ?
N3 C3 C2 C1 45.97(15) . . . . ?
C3 C12 C11 O4 -49.6(2) . . . . ?
C3 C12 C11 N2 132.01(13) . . . . ?
C3 C4 C19 N1 31.99(14) . . . . ?
C3 C2 C1 F2 35.37(19) . . . . ?
C3 C2 C1 F3 -83.85(17) . . . . ?
C3 C2 C1 F1 156.22(14) . . . . ?
C13 C12 C11 O4 -177.87(15) . . . . ?
C13 C12 C11 N2 3.79(15) . . . . ?
C13 C18 C17 C16 0.4(3) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
C12 N1 C19 C4 -47.92(14) . . . . ?
C12 C3 C4 C5 111.19(12) . . . . ?
C12 C3 C4 C19 -6.86(13) . . . . ?
C12 C3 C2 O1 -72.23(14) . . . . ?
C12 C3 C2 C1 161.87(12) . . . . ?
C12 C13 C18 N2 0.32(18) . . . . ?
C12 C13 C18 C17 -178.00(15) . . . . ?
C12 C13 C14 C15 177.40(15) . . . . ?
C5 C10 C9 C8 -1.0(2) . . . . ?
C5 C4 C19 N1 -88.72(13) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C11 N2 C18 C13 2.4(2) . . . . ?
C11 N2 C18 C17 -179.41(17) . . . . ?
C10 O1 C2 C3 -58.85(15) . . . . ?
C10 O1 C2 C1 70.15(15) . . . . ?
C10 C5 C4 C3 -13.72(19) . . . . ?
C10 C5 C4 C19 101.02(15) . . . . ?
C10 C5 C6 C7 -1.0(2) . . . . ?
C10 C9 C8 C7 -0.4(3) . . . . ?
C4 C3 C12 N1 -20.22(12) . . . . ?
C4 C3 C12 C13 -144.74(12) . . . . ?
C4 C3 C12 C11 98.45(12) . . . . ?
C4 C3 C2 O1 47.95(15) . . . . ?
C4 C3 C2 C1 -77.95(15) . . . . ?
C4 C5 C10 O1 5.4(2) . . . . ?
C4 C5 C10 C9 -172.18(14) . . . . ?
C4 C5 C6 C7 172.89(15) . . . . ?
C2 O1 C10 C5 33.14(17) . . . . ?
C2 O1 C10 C9 -149.15(13) . . . . ?
C2 C3 C12 N1 104.59(12) . . . . ?
C2 C3 C12 C13 -19.94(16) . . . . ?
C2 C3 C12 C11 -136.74(12) . . . . ?
C2 C3 C4 C5 -12.96(17) . . . . ?
C2 C3 C4 C19 -131.02(12) . . . . ?
C18 N2 C11 O4 177.74(15) . . . . ?
C18 N2 C11 C12 -3.91(18) . . . . ?
C18 C13 C12 N1 117.54(14) . . . . ?
C18 C13 C12 C3 -123.91(13) . . . . ?
C18 C13 C12 C11 -2.39(15) . . . . ?
C18 C13 C14 C15 3.1(2) . . . . ?
C14 C13 C12 N1 -57.2(2) . . . . ?
C14 C13 C12 C3 61.3(2) . . . . ?
C14 C13 C12 C11 -177.18(16) . . . . ?
C14 C13 C18 N2 175.85(14) . . . . ?
C14 C13 C18 C17 -2.5(2) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C19 N1 C12 C3 42.07(13) . . . . ?
C19 N1 C12 C13 171.49(11) . . . . ?
C19 N1 C12 C11 -75.25(14) . . . . ?
C6 C5 C10 O1 179.21(13) . . . . ?
C6 C5 C10 C9 1.6(2) . . . . ?
C6 C5 C4 C3 172.67(13) . . . . ?
C6 C5 C4 C19 -72.59(17) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C20 N1 C12 C3 169.77(13) . . . . ?
C20 N1 C12 C13 -60.81(17) . . . . ?
C20 N1 C12 C11 52.45(16) . . . . ?
C20 N1 C19 C4 -176.23(13) . . . . ?
