# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_0417JFC2_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2213890'
loop_
_audit_author_name
_audit_author_address
'wei wang'
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2023-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-(4-acetylphenyl)-2,2,5,5,5-pentafluoro-N-phenylpentanamide
_chemical_name_common            4kh
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 F5 N O2'
_chemical_formula_weight         385.33

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.161(2)
_cell_length_b                   10.353(3)
_cell_length_c                   20.984(6)
_cell_angle_alpha                79.398(7)
_cell_angle_beta                 85.889(7)
_cell_angle_gamma                89.958(7)
_cell_volume                     1738.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2322
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      21.45

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6011
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         0.990
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6011
_reflns_number_gt                2808
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6011
_refine_ls_number_parameters     442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2571
_refine_ls_wR_factor_gt          0.1962
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0724(15) 0.1510(8) 0.0515(4) 0.101(3) Uani 1 1 d . . . . .
H1A H 0.9783 0.1885 0.0710 0.152 Uiso 1 1 calc R U . . .
H1B H 1.0478 0.1334 0.0098 0.152 Uiso 1 1 calc R U . . .
H1C H 1.1636 0.2115 0.0461 0.152 Uiso 1 1 calc R U . . .
C2 C 1.1153(11) 0.0260(9) 0.0943(4) 0.073(3) Uani 1 1 d . . . . .
C3 C 1.0960(6) 0.0148(4) 0.16684(14) 0.056(2) Uani 1 1 d G . . . .
C8 C 1.0266(6) 0.1140(3) 0.1960(2) 0.059(2) Uani 1 1 d G . . . .
H8 H 0.9933 0.1914 0.1704 0.071 Uiso 1 1 calc R U . . .
C7 C 1.0067(6) 0.0977(4) 0.2633(2) 0.0569(19) Uani 1 1 d G . . . .
H7 H 0.9603 0.1641 0.2828 0.068 Uiso 1 1 calc R U . . .
C6 C 1.0564(6) -0.0179(4) 0.30156(14) 0.0533(19) Uani 1 1 d G . . . .
C5 C 1.1259(7) -0.1171(3) 0.2724(2) 0.059(2) Uani 1 1 d G . . . .
H5 H 1.1591 -0.1945 0.2980 0.071 Uiso 1 1 calc R U . . .
C4 C 1.1457(6) -0.1008(4) 0.2051(2) 0.063(2) Uani 1 1 d G . . . .
H4 H 1.1922 -0.1672 0.1856 0.075 Uiso 1 1 calc R U . . .
C9 C 1.1905(12) -0.0446(9) 0.4074(4) 0.075(2) Uani 1 1 d . . . . .
C10 C 1.0278(10) -0.0326(6) 0.3757(3) 0.059(2) Uani 1 1 d . . . . .
H10 H 0.9768 0.0487 0.3845 0.071 Uiso 1 1 calc R U . . .
C11 C 0.9117(10) -0.1476(8) 0.4088(3) 0.066(2) Uani 1 1 d . . . . .
H11A H 0.9500 -0.2280 0.3955 0.079 Uiso 1 1 calc R U . . .
H11B H 0.9163 -0.1590 0.4555 0.079 Uiso 1 1 calc R U . . .
C12 C 0.7337(10) -0.1254(6) 0.3919(3) 0.0525(18) Uani 1 1 d . . . . .
C13 C 0.6990(9) -0.1366(6) 0.3239(3) 0.0516(18) Uani 1 1 d . . . . .
C14 C 0.6103(6) -0.0099(5) 0.22075(15) 0.0501(18) Uani 1 1 d G . . . .
C15 C 0.6766(6) -0.0897(4) 0.1792(2) 0.063(2) Uani 1 1 d G . . . .
H15 H 0.7342 -0.1645 0.1958 0.076 Uiso 1 1 calc R U . . .
C16 C 0.6567(7) -0.0579(5) 0.1130(2) 0.075(2) Uani 1 1 d G . . . .
H16 H 0.7011 -0.1113 0.0852 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5706(8) 0.0539(5) 0.08822(15) 0.075(3) Uani 1 1 d G . . . .
H17 H 0.5573 0.0752 0.0439 0.090 Uiso 1 1 calc R U . . .
C18 C 0.5043(7) 0.1337(4) 0.1297(2) 0.076(3) Uani 1 1 d G . . . .
H18 H 0.4467 0.2085 0.1132 0.091 Uiso 1 1 calc R U . . .
C19 C 0.5242(6) 0.1019(4) 0.1960(2) 0.062(2) Uani 1 1 d G . . . .
H19 H 0.4798 0.1553 0.2238 0.075 Uiso 1 1 calc R U . . .
C20 C 0.4128(16) 0.6504(7) 0.0521(3) 0.099(4) Uani 1 1 d . . . . .
H20A H 0.3503 0.7229 0.0629 0.149 Uiso 1 1 calc R U . . .
H20B H 0.4022 0.6454 0.0073 0.149 Uiso 1 1 calc R U . . .
H20C H 0.5264 0.6630 0.0588 0.149 Uiso 1 1 calc R U . . .
C21 C 0.3494(11) 0.5245(7) 0.0947(3) 0.063(2) Uani 1 1 d . . . . .
C22 C 0.3474(7) 0.5127(4) 0.16777(14) 0.056(2) Uani 1 1 d G . . . .
C27 C 0.4066(6) 0.6128(3) 0.1962(2) 0.060(2) Uani 1 1 d G . . . .
H27 H 0.4479 0.6901 0.1701 0.072 Uiso 1 1 calc R U . . .
C26 C 0.4040(6) 0.5975(4) 0.2634(2) 0.0567(19) Uani 1 1 d G . . . .
H26 H 0.4436 0.6645 0.2824 0.068 Uiso 1 1 calc R U . . .
C25 C 0.3422(6) 0.4820(4) 0.30233(14) 0.0552(19) Uani 1 1 d G . . . .
C24 C 0.2830(6) 0.3819(3) 0.2739(2) 0.063(2) Uani 1 1 d G . . . .
H24 H 0.2416 0.3047 0.3000 0.075 Uiso 1 1 calc R U . . .
C23 C 0.2856(6) 0.3972(4) 0.2067(2) 0.062(2) Uani 1 1 d G . . . .
H23 H 0.2459 0.3303 0.1877 0.075 Uiso 1 1 calc R U . . .
C28 C 0.1707(13) 0.4562(9) 0.4084(4) 0.077(2) Uani 1 1 d . . . . .
C29 C 0.3432(9) 0.4677(6) 0.3762(3) 0.0548(18) Uani 1 1 d . . . . .
H29 H 0.3902 0.5496 0.3845 0.066 Uiso 1 1 calc R U . . .
C30 C 0.4487(11) 0.3564(7) 0.4091(3) 0.059(2) Uani 1 1 d . . . . .
H30A H 0.4260 0.3458 0.4558 0.071 Uiso 1 1 calc R U . . .
H30B H 0.4163 0.2754 0.3962 0.071 Uiso 1 1 calc R U . . .
C31 C 0.6278(12) 0.3767(7) 0.3937(3) 0.063(2) Uani 1 1 d . . . . .
C32 C 0.6884(10) 0.3608(7) 0.3237(3) 0.0553(19) Uani 1 1 d . . . . .
C33 C 0.8120(6) 0.4897(4) 0.22069(16) 0.0508(18) Uani 1 1 d G . . . .
C34 C 0.7584(6) 0.4103(4) 0.1794(2) 0.070(2) Uani 1 1 d G . . . .
H34 H 0.6935 0.3364 0.1963 0.084 Uiso 1 1 calc R U . . .
C35 C 0.8019(8) 0.4414(5) 0.1131(2) 0.087(3) Uani 1 1 d G . . . .
H35 H 0.7660 0.3882 0.0855 0.104 Uiso 1 1 calc R U . . .
C36 C 0.8989(8) 0.5518(6) 0.08799(16) 0.083(3) Uani 1 1 d G . . . .
H36 H 0.9279 0.5726 0.0436 0.100 Uiso 1 1 calc R U . . .
C37 C 0.9524(6) 0.6312(4) 0.1292(3) 0.075(2) Uani 1 1 d G . . . .
H37 H 1.0173 0.7051 0.1124 0.090 Uiso 1 1 calc R U . . .
C38 C 0.9090(6) 0.6001(4) 0.1956(2) 0.067(2) Uani 1 1 d G . . . .
H38 H 0.9449 0.6533 0.2232 0.081 Uiso 1 1 calc R U . . .
F1 F 1.2666(7) -0.1568(5) 0.4042(3) 0.1031(18) Uani 1 1 d . . . . .
F2 F 1.2942(7) 0.0512(5) 0.3780(3) 0.1097(18) Uani 1 1 d . . . . .
F3 F 1.1734(7) -0.0392(5) 0.4696(2) 0.1119(17) Uani 1 1 d . . . . .
F4 F 0.6800(6) -0.0089(4) 0.40631(18) 0.0716(13) Uani 1 1 d . . . . .
F5 F 0.6397(7) -0.2193(4) 0.43345(18) 0.0879(15) Uani 1 1 d . . . . .
F6 F 0.0733(7) 0.5478(5) 0.3800(2) 0.1093(17) Uani 1 1 d . . . . .
F7 F 0.0996(8) 0.3395(6) 0.4064(3) 0.114(2) Uani 1 1 d . . . . .
F8 F 0.1667(8) 0.4645(6) 0.4710(2) 0.1183(19) Uani 1 1 d . . . . .
F9 F 0.7060(7) 0.2818(4) 0.43399(19) 0.0875(14) Uani 1 1 d . . . . .
F10 F 0.6761(6) 0.4935(4) 0.40720(19) 0.0805(14) Uani 1 1 d . . . . .
N1 N 0.6368(8) -0.0309(5) 0.2871(2) 0.0561(16) Uani 1 1 d . . . . .
H1 H 0.6094 0.0325 0.3069 0.067 Uiso 1 1 calc R U . . .
N2 N 0.7626(7) 0.4713(5) 0.2881(2) 0.0502(15) Uani 1 1 d . . . . .
H2 H 0.7810 0.5348 0.3080 0.060 Uiso 1 1 calc R U . . .
O1 O 1.1685(10) -0.0652(5) 0.0714(3) 0.093(2) Uani 1 1 d . . . . .
O2 O 0.7303(7) -0.2421(4) 0.3056(2) 0.0646(14) Uani 1 1 d . . . . .
O3 O 0.6590(7) 0.2590(4) 0.3066(2) 0.0678(15) Uani 1 1 d . . . . .
O4 O 0.3061(9) 0.4336(5) 0.0715(2) 0.089(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
C1 C2 1.490(11) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.202(9) . ?
C2 C3 1.502(8) . ?
C3 C8 1.3900 . ?
C3 C4 1.3900 . ?
C8 C7 1.3900 . ?
C8 H8 0.9300 . ?
C7 C6 1.3900 . ?
C7 H7 0.9300 . ?
C6 C5 1.3900 . ?
C6 C10 1.536(7) . ?
C5 C4 1.3900 . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C9 F3 1.315(8) . ?
C9 F1 1.327(9) . ?
C9 F2 1.335(10) . ?
C9 C10 1.522(11) . ?
C10 C11 1.550(10) . ?
C10 H10 0.9800 . ?
C11 C12 1.527(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 F4 1.361(7) . ?
C12 F5 1.374(8) . ?
C12 C13 1.499(9) . ?
C13 O2 1.243(7) . ?
C13 N1 1.341(8) . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C14 N1 1.402(6) . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.508(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O4 1.200(8) . ?
C21 C22 1.514(7) . ?
C22 C27 1.3900 . ?
C22 C23 1.3900 . ?
C27 C26 1.3900 . ?
C27 H27 0.9300 . ?
C26 C25 1.3900 . ?
C26 H26 0.9300 . ?
C25 C24 1.3900 . ?
C25 C29 1.531(6) . ?
C24 C23 1.3900 . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C28 F6 1.321(9) . ?
C28 F8 1.330(8) . ?
C28 F7 1.349(10) . ?
C28 C29 1.512(13) . ?
C29 C30 1.529(10) . ?
C29 H29 0.9800 . ?
C30 C31 1.481(13) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 F10 1.357(8) . ?
C31 F9 1.362(8) . ?
C31 C32 1.555(10) . ?
C32 O3 1.203(7) . ?
C32 N2 1.362(8) . ?
C33 C34 1.3900 . ?
C33 C38 1.3900 . ?
C33 N2 1.421(6) . ?
C34 C35 1.3900 . ?
C34 H34 0.9300 . ?
C35 C36 1.3900 . ?
C35 H35 0.9300 . ?
C36 C37 1.3900 . ?
C36 H36 0.9300 . ?
C37 C38 1.3900 . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 120.7(7) . . ?
O1 C2 C3 119.6(7) . . ?
C1 C2 C3 119.7(7) . . ?
C8 C3 C4 120.0 . . ?
C8 C3 C2 122.0(5) . . ?
C4 C3 C2 118.0(5) . . ?
C7 C8 C3 120.0 . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 C10 118.0(4) . . ?
C5 C6 C10 122.0(4) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
F3 C9 F1 105.2(7) . . ?
F3 C9 F2 108.3(7) . . ?
F1 C9 F2 106.3(8) . . ?
F3 C9 C10 112.7(8) . . ?
F1 C9 C10 113.5(7) . . ?
F2 C9 C10 110.4(7) . . ?
C9 C10 C6 110.7(6) . . ?
C9 C10 C11 109.6(6) . . ?
C6 C10 C11 115.0(5) . . ?
C9 C10 H10 107.1 . . ?
C6 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C12 C11 C10 112.8(6) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
F4 C12 F5 104.8(6) . . ?
F4 C12 C13 111.0(6) . . ?
F5 C12 C13 107.4(6) . . ?
F4 C12 C11 110.3(6) . . ?
F5 C12 C11 106.9(6) . . ?
C13 C12 C11 115.7(6) . . ?
O2 C13 N1 124.7(6) . . ?
O2 C13 C12 118.2(6) . . ?
N1 C13 C12 117.1(6) . . ?
C15 C14 C19 120.0 . . ?
C15 C14 N1 122.7(4) . . ?
C19 C14 N1 117.1(4) . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C20 120.9(7) . . ?
O4 C21 C22 120.3(6) . . ?
C20 C21 C22 118.7(6) . . ?
C27 C22 C23 120.0 . . ?
C27 C22 C21 121.8(4) . . ?
C23 C22 C21 118.2(4) . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 C29 118.6(4) . . ?
C24 C25 C29 121.3(4) . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
F6 C28 F8 107.6(7) . . ?
F6 C28 F7 106.5(8) . . ?
F8 C28 F7 105.7(7) . . ?
F6 C28 C29 112.2(7) . . ?
F8 C28 C29 112.5(8) . . ?
F7 C28 C29 111.9(7) . . ?
C28 C29 C25 111.4(6) . . ?
C28 C29 C30 110.1(6) . . ?
C25 C29 C30 115.2(5) . . ?
C28 C29 H29 106.5 . . ?
C25 C29 H29 106.5 . . ?
C30 C29 H29 106.5 . . ?
C31 C30 C29 114.6(6) . . ?
C31 C30 H30A 108.6 . . ?
C29 C30 H30A 108.6 . . ?
C31 C30 H30B 108.6 . . ?
C29 C30 H30B 108.6 . . ?
H30A C30 H30B 107.6 . . ?
F10 C31 F9 106.5(6) . . ?
F10 C31 C30 110.4(7) . . ?
F9 C31 C30 107.8(6) . . ?
F10 C31 C32 111.9(6) . . ?
F9 C31 C32 105.4(6) . . ?
C30 C31 C32 114.4(6) . . ?
O3 C32 N2 128.4(6) . . ?
O3 C32 C31 118.3(7) . . ?
N2 C32 C31 113.1(6) . . ?
C34 C33 C38 120.0 . . ?
C34 C33 N2 123.6(4) . . ?
C38 C33 N2 116.2(4) . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C33 120.0 . . ?
C37 C38 H38 120.0 . . ?
C33 C38 H38 120.0 . . ?
C13 N1 C14 128.7(5) . . ?
C13 N1 H1 115.7 . . ?
C14 N1 H1 115.7 . . ?
C32 N2 C33 125.0(5) . . ?
C32 N2 H2 117.5 . . ?
C33 N2 H2 117.5 . . ?

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 C2 C3 C8 -176.3(6) . . . . ?
C1 C2 C3 C8 5.3(10) . . . . ?
O1 C2 C3 C4 1.8(10) . . . . ?
C1 C2 C3 C4 -176.6(7) . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
C2 C3 C8 C7 178.1(6) . . . . ?
C3 C8 C7 C6 0.0 . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C8 C7 C6 C10 -178.5(5) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C10 C6 C5 C4 178.4(5) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C5 -178.2(5) . . . . ?
F3 C9 C10 C6 171.2(6) . . . . ?
F1 C9 C10 C6 -69.2(9) . . . . ?
F2 C9 C10 C6 50.0(8) . . . . ?
F3 C9 C10 C11 -61.0(9) . . . . ?
F1 C9 C10 C11 58.6(9) . . . . ?
F2 C9 C10 C11 177.8(6) . . . . ?
C7 C6 C10 C9 -117.2(6) . . . . ?
C5 C6 C10 C9 64.4(7) . . . . ?
C7 C6 C10 C11 118.0(5) . . . . ?
C5 C6 C10 C11 -60.4(7) . . . . ?
C9 C10 C11 C12 165.9(6) . . . . ?
C6 C10 C11 C12 -68.8(8) . . . . ?
C10 C11 C12 F4 -54.9(7) . . . . ?
C10 C11 C12 F5 -168.3(5) . . . . ?
C10 C11 C12 C13 72.1(8) . . . . ?
F4 C12 C13 O2 -174.8(6) . . . . ?
F5 C12 C13 O2 -60.7(9) . . . . ?
C11 C12 C13 O2 58.6(9) . . . . ?
F4 C12 C13 N1 5.6(9) . . . . ?
F5 C12 C13 N1 119.6(7) . . . . ?
C11 C12 C13 N1 -121.1(7) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
N1 C14 C15 C16 -174.9(5) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
N1 C14 C19 C18 175.2(5) . . . . ?
O4 C21 C22 C27 175.8(7) . . . . ?
C20 C21 C22 C27 -1.9(10) . . . . ?
O4 C21 C22 C23 -3.6(10) . . . . ?
C20 C21 C22 C23 178.7(7) . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C21 C22 C27 C26 -179.3(6) . . . . ?
C22 C27 C26 C25 0.0 . . . . ?
C27 C26 C25 C24 0.0 . . . . ?
C27 C26 C25 C29 179.2(5) . . . . ?
C26 C25 C24 C23 0.0 . . . . ?
C29 C25 C24 C23 -179.2(5) . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C21 C22 C23 C24 179.4(5) . . . . ?
F6 C28 C29 C25 -48.6(9) . . . . ?
F8 C28 C29 C25 -170.1(5) . . . . ?
F7 C28 C29 C25 71.1(8) . . . . ?
F6 C28 C29 C30 -177.7(6) . . . . ?
F8 C28 C29 C30 60.8(9) . . . . ?
F7 C28 C29 C30 -58.0(9) . . . . ?
C26 C25 C29 C28 116.4(6) . . . . ?
C24 C25 C29 C28 -64.4(7) . . . . ?
C26 C25 C29 C30 -117.3(6) . . . . ?
C24 C25 C29 C30 62.0(7) . . . . ?
C28 C29 C30 C31 -164.7(7) . . . . ?
C25 C29 C30 C31 68.3(8) . . . . ?
C29 C30 C31 F10 54.4(8) . . . . ?
C29 C30 C31 F9 170.4(5) . . . . ?
C29 C30 C31 C32 -72.8(8) . . . . ?
F10 C31 C32 O3 177.2(7) . . . . ?
F9 C31 C32 O3 61.8(9) . . . . ?
C30 C31 C32 O3 -56.4(10) . . . . ?
F10 C31 C32 N2 -6.2(9) . . . . ?
F9 C31 C32 N2 -121.5(7) . . . . ?
C30 C31 C32 N2 120.3(7) . . . . ?
C38 C33 C34 C35 0.0 . . . . ?
N2 C33 C34 C35 174.7(5) . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C36 C37 C38 C33 0.0 . . . . ?
C34 C33 C38 C37 0.0 . . . . ?
N2 C33 C38 C37 -175.1(5) . . . . ?
O2 C13 N1 C14 -7.4(11) . . . . ?
C12 C13 N1 C14 172.3(6) . . . . ?
C15 C14 N1 C13 -13.1(9) . . . . ?
C19 C14 N1 C13 171.8(6) . . . . ?
O3 C32 N2 C33 4.1(12) . . . . ?
C31 C32 N2 C33 -172.2(6) . . . . ?
C34 C33 N2 C32 15.1(8) . . . . ?
C38 C33 N2 C32 -170.0(5) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.091



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane/EtOAc'
