# 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_aml_209
_database_code_depnum_ccdc_archive 'CCDC 2295985'
loop_
_audit_author_name
_audit_author_address
'Jeremy Forte'
;Sorbonne Universite, CNRS
France
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-12-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 F3 N O'
_chemical_formula_sum            'C16 H16 F3 N O'
_chemical_formula_weight         295.30
_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 0.0181 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'
F F 0.0727 0.0534 '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'

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

_cell_length_a                   7.4696(3)
_cell_length_b                   19.5327(8)
_cell_length_c                   10.1253(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.184(2)
_cell_angle_gamma                90
_cell_volume                     1386.57(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3643
_cell_measurement_temperature    200.02
_cell_measurement_theta_max      66.37
_cell_measurement_theta_min      4.53
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0878 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.8765.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.175
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10353
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.478
_diffrn_reflns_theta_max         66.478
_diffrn_reflns_theta_min         4.527
_diffrn_ambient_temperature      200.02
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   micro-focus
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2027
_reflns_number_total             2418
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.6236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1020
_refine_special_details          ?

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.00327(14) 0.26156(6) 0.57645(12) 0.0486(3) Uani 1 1 d . . . . .
F2 F 0.72352(17) 0.22006(6) 0.53497(15) 0.0594(4) Uani 1 1 d . . . . .
F3 F 0.81359(18) 0.24990(7) 0.36384(13) 0.0637(4) Uani 1 1 d . . . . .
O1 O 0.11305(17) 0.39892(8) 0.44301(15) 0.0491(4) Uani 1 1 d . . . . .
N1 N 0.40041(18) 0.34847(8) 0.46934(14) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.2460(2) 0.38721(10) 0.40161(19) 0.0337(4) Uani 1 1 d . . . . .
C2 C 0.2701(2) 0.41254(10) 0.26803(19) 0.0365(4) Uani 1 1 d . . . . .
H2A H 0.225466 0.460406 0.247871 0.044 Uiso 1 1 calc R U . . .
H2B H 0.198857 0.383390 0.186941 0.044 Uiso 1 1 calc R U . . .
C3 C 0.4853(2) 0.40746(9) 0.29897(17) 0.0291(4) Uani 1 1 d . . . . .
C4 C 0.5948(3) 0.47496(9) 0.35510(19) 0.0363(4) Uani 1 1 d . . . . .
H4A H 0.511426 0.513398 0.360866 0.044 Uiso 1 1 calc R U . . .
H4B H 0.702774 0.469462 0.444702 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6547(4) 0.47756(12) 0.2260(3) 0.0607(6) Uani 1 1 d . . . . .
H5A H 0.794721 0.476515 0.248950 0.073 Uiso 1 1 calc R U . . .
H5B H 0.597303 0.516179 0.162075 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5586(3) 0.40913(10) 0.17408(19) 0.0377(4) Uani 1 1 d . . . . .
H6A H 0.649188 0.371815 0.175990 0.045 Uiso 1 1 calc R U . . .
H6B H 0.455728 0.411733 0.081113 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5357(2) 0.34410(8) 0.39408(17) 0.0266(4) Uani 1 1 d . . . . .
H7 H 0.505643 0.302298 0.333351 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7445(2) 0.33928(8) 0.49504(17) 0.0268(4) Uani 1 1 d . . . . .
H8 H 0.821823 0.371120 0.458865 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8212(3) 0.26817(10) 0.4930(2) 0.0390(4) Uani 1 1 d . . . . .
C10 C 0.7732(2) 0.36042(8) 0.64529(17) 0.0265(4) Uani 1 1 d . . . . .
C11 C 0.9410(2) 0.39209(9) 0.72705(18) 0.0308(4) Uani 1 1 d . . . . .
H11 H 1.036314 0.402246 0.687555 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9707(3) 0.40901(10) 0.86570(19) 0.0379(4) Uani 1 1 d . . . . .
H12 H 1.085822 0.430885 0.920875 0.045 Uiso 1 1 calc R U . . .
C13 C 0.8330(3) 0.39410(11) 0.92397(19) 0.0418(5) Uani 1 1 d . . . . .
H13 H 0.854358 0.404818 1.019722 0.050 Uiso 1 1 calc R U . . .
C14 C 0.6638(2) 0.36350(11) 0.84235(18) 0.0388(4) Uani 1 1 d . . . . .
H14 H 0.568859 0.353699 0.882445 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6312(2) 0.34697(9) 0.70272(17) 0.0308(4) Uani 1 1 d . . . . .
C16 C 0.4423(2) 0.31899(10) 0.60801(18) 0.0366(4) Uani 1 1 d . . . . .
H16A H 0.448865 0.268484 0.602789 0.044 Uiso 1 1 calc R U . . .
H16B H 0.340577 0.331004 0.645818 0.044 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 C9 1.337(2) . ?
F2 C9 1.345(2) . ?
F3 C9 1.338(2) . ?
O1 C1 1.225(2) . ?
N1 C1 1.352(2) . ?
N1 C7 1.4634(19) . ?
N1 C16 1.448(2) . ?
C1 C2 1.508(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(2) . ?
C3 C4 1.552(2) . ?
C3 C6 1.542(2) . ?
C3 C7 1.533(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.522(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C7 C8 1.545(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.505(2) . ?
C8 C10 1.519(2) . ?
C10 C11 1.387(2) . ?
C10 C15 1.399(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 C16 1.508(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 112.98(13) . . ?
C1 N1 C16 125.13(14) . . ?
C16 N1 C7 121.64(13) . . ?
O1 C1 N1 125.54(17) . . ?
O1 C1 C2 127.40(16) . . ?
N1 C1 C2 107.05(13) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C1 C2 C3 103.73(13) . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C2 C3 C4 113.78(14) . . ?
C2 C3 C6 118.40(14) . . ?
C2 C3 C7 101.17(13) . . ?
C6 C3 C4 89.49(13) . . ?
C7 C3 C4 118.13(14) . . ?
C7 C3 C6 116.89(14) . . ?
C3 C4 H4A 113.8 . . ?
C3 C4 H4B 113.8 . . ?
H4A C4 H4B 111.0 . . ?
C5 C4 C3 89.29(14) . . ?
C5 C4 H4A 113.8 . . ?
C5 C4 H4B 113.8 . . ?
C4 C5 H5A 113.4 . . ?
C4 C5 H5B 113.4 . . ?
C4 C5 C6 91.37(14) . . ?
H5A C5 H5B 110.7 . . ?
C6 C5 H5A 113.4 . . ?
C6 C5 H5B 113.4 . . ?
C3 C6 H6A 113.7 . . ?
C3 C6 H6B 113.7 . . ?
C5 C6 C3 89.66(14) . . ?
C5 C6 H6A 113.7 . . ?
C5 C6 H6B 113.7 . . ?
H6A C6 H6B 110.9 . . ?
N1 C7 C3 102.47(12) . . ?
N1 C7 H7 108.6 . . ?
N1 C7 C8 112.34(13) . . ?
C3 C7 H7 108.6 . . ?
C3 C7 C8 115.97(13) . . ?
C8 C7 H7 108.6 . . ?
C7 C8 H8 107.4 . . ?
C9 C8 C7 110.44(14) . . ?
C9 C8 H8 107.4 . . ?
C9 C8 C10 109.98(14) . . ?
C10 C8 C7 114.04(13) . . ?
C10 C8 H8 107.4 . . ?
F1 C9 F2 106.10(15) . . ?
F1 C9 F3 106.44(14) . . ?
F1 C9 C8 112.91(15) . . ?
F2 C9 C8 112.94(15) . . ?
F3 C9 F2 106.12(16) . . ?
F3 C9 C8 111.80(16) . . ?
C11 C10 C8 120.33(14) . . ?
C11 C10 C15 119.63(15) . . ?
C15 C10 C8 120.03(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.50(15) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.03(17) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.80(17) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.78(16) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C16 118.72(15) . . ?
C14 C15 C10 119.22(16) . . ?
C14 C15 C16 121.95(15) . . ?
N1 C16 C15 108.32(13) . . ?
N1 C16 H16A 110.0 . . ?
N1 C16 H16B 110.0 . . ?
C15 C16 H16A 110.0 . . ?
C15 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 157.99(18) . . . . ?
N1 C1 C2 C3 -21.94(19) . . . . ?
N1 C7 C8 C9 107.64(16) . . . . ?
N1 C7 C8 C10 -16.81(19) . . . . ?
C1 N1 C7 C3 21.51(18) . . . . ?
C1 N1 C7 C8 146.66(15) . . . . ?
C1 N1 C16 C15 -119.81(18) . . . . ?
C1 C2 C3 C4 -94.23(17) . . . . ?
C1 C2 C3 C6 162.64(16) . . . . ?
C1 C2 C3 C7 33.52(17) . . . . ?
C2 C3 C4 C5 -117.76(17) . . . . ?
C2 C3 C6 C5 113.68(18) . . . . ?
C2 C3 C7 N1 -32.91(16) . . . . ?
C2 C3 C7 C8 -155.65(14) . . . . ?
C3 C4 C5 C6 -3.33(16) . . . . ?
C3 C7 C8 C9 -134.99(15) . . . . ?
C3 C7 C8 C10 100.57(16) . . . . ?
C4 C3 C6 C5 -3.29(16) . . . . ?
C4 C3 C7 N1 91.95(16) . . . . ?
C4 C3 C7 C8 -30.8(2) . . . . ?
C4 C5 C6 C3 3.36(16) . . . . ?
C6 C3 C4 C5 3.29(15) . . . . ?
C6 C3 C7 N1 -162.99(14) . . . . ?
C6 C3 C7 C8 74.28(19) . . . . ?
C7 N1 C1 O1 -179.75(17) . . . . ?
C7 N1 C1 C2 0.2(2) . . . . ?
C7 N1 C16 C15 54.0(2) . . . . ?
C7 C3 C4 C5 123.83(17) . . . . ?
C7 C3 C6 C5 -124.90(17) . . . . ?
C7 C8 C9 F1 178.61(14) . . . . ?
C7 C8 C9 F2 -61.00(19) . . . . ?
C7 C8 C9 F3 58.61(19) . . . . ?
C7 C8 C10 C11 -146.91(15) . . . . ?
C7 C8 C10 C15 34.1(2) . . . . ?
C8 C10 C11 C12 -177.47(16) . . . . ?
C8 C10 C15 C14 176.75(16) . . . . ?
C8 C10 C15 C16 -7.1(2) . . . . ?
C9 C8 C10 C11 88.40(19) . . . . ?
C9 C8 C10 C15 -90.56(18) . . . . ?
C10 C8 C9 F1 -54.65(19) . . . . ?
C10 C8 C9 F2 65.74(18) . . . . ?
C10 C8 C9 F3 -174.65(14) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C10 C15 C16 N1 -34.4(2) . . . . ?
C11 C10 C15 C14 -2.2(3) . . . . ?
C11 C10 C15 C16 173.98(16) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C10 1.2(3) . . . . ?
C13 C14 C15 C16 -174.88(18) . . . . ?
C14 C15 C16 N1 141.72(17) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C16 N1 C1 O1 -5.5(3) . . . . ?
C16 N1 C1 C2 174.46(16) . . . . ?
C16 N1 C7 C3 -153.00(15) . . . . ?
C16 N1 C7 C8 -27.8(2) . . . . ?


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

data_aml114
_database_code_depnum_ccdc_archive 'CCDC 2295988'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Gontard'
;Sorbonne Universite
France
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C15 H14 F3 N O'
_chemical_formula_sum            'C15 H14 F3 N O'
_chemical_formula_weight         281.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7312(2)
_cell_length_b                   24.6023(7)
_cell_length_c                   8.2365(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.277(2)
_cell_angle_gamma                90
_cell_volume                     1279.46(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    2834
_cell_measurement_theta_min      6.01
_cell_measurement_theta_max      68.01

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            8124
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.593
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2249
_reflns_number_gt                1909
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.4014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2249
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.041

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 0.8272(2) 0.29664(6) 0.4259(2) 0.0813(5) Uani 1 1 d . . . . .
F2 F 1.00271(18) 0.35468(6) 0.61507(19) 0.0710(4) Uani 1 1 d . . . . .
F3 F 0.7711(2) 0.30434(5) 0.66479(17) 0.0640(4) Uani 1 1 d . . . . .
O1 O -0.0464(2) 0.42935(6) 0.26151(18) 0.0523(4) Uani 1 1 d . . . . .
N1 N 0.2825(2) 0.39209(6) 0.39588(18) 0.0375(3) Uani 1 1 d . . . . .
C1 C 0.4229(3) 0.35079(7) 0.3653(2) 0.0382(4) Uani 1 1 d . . . . .
H1 H 0.408973 0.316553 0.425859 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6456(3) 0.37505(7) 0.4584(2) 0.0387(4) Uani 1 1 d . . . . .
H2 H 0.690155 0.395930 0.372550 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6071(3) 0.41474(7) 0.5862(2) 0.0370(4) Uani 1 1 d . . . . .
C4 C 0.3911(3) 0.42465(7) 0.5392(2) 0.0359(4) Uani 1 1 d . . . . .
C5 C 0.3275(3) 0.34130(7) 0.1690(2) 0.0441(4) Uani 1 1 d . . . . .
C6 C 0.0927(3) 0.35410(9) 0.1346(3) 0.0501(5) Uani 1 1 d . . . . .
H6A H 0.023530 0.367942 0.015346 0.060 Uiso 1 1 calc R U . . .
H6B H 0.016599 0.321174 0.149981 0.060 Uiso 1 1 calc R U . . .
C7 C 0.0932(3) 0.39703(8) 0.2659(2) 0.0415(4) Uani 1 1 d . . . . .
C8 C 0.3729(4) 0.28693(9) 0.0952(3) 0.0612(6) Uani 1 1 d . . . . .
H8A H 0.491015 0.266068 0.177257 0.073 Uiso 1 1 calc R U . . .
H8B H 0.245971 0.263755 0.045420 0.073 Uiso 1 1 calc R U . . .
C9 C 0.4339(5) 0.31782(11) -0.0385(3) 0.0746(7) Uani 1 1 d . . . . .
H9A H 0.328746 0.314623 -0.156956 0.090 Uiso 1 1 calc R U . . .
H9B H 0.577752 0.308937 -0.037654 0.090 Uiso 1 1 calc R U . . .
C10 C 0.4227(4) 0.37158(9) 0.0479(3) 0.0510(5) Uani 1 1 d . . . . .
H10A H 0.324948 0.398213 -0.029790 0.061 Uiso 1 1 calc R U . . .
H10B H 0.562829 0.388130 0.109063 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8102(3) 0.33289(9) 0.5416(3) 0.0516(5) Uani 1 1 d . . . . .
C12 C 0.7473(3) 0.44283(8) 0.7251(2) 0.0466(5) Uani 1 1 d . . . . .
H12 H 0.895641 0.437153 0.757958 0.056 Uiso 1 1 calc R U . . .
C13 C 0.6667(4) 0.47943(8) 0.8152(2) 0.0515(5) Uani 1 1 d . . . . .
H13 H 0.760862 0.498085 0.912515 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4531(3) 0.48892(8) 0.7655(2) 0.0482(5) Uani 1 1 d . . . . .
H14 H 0.402011 0.514419 0.828233 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3098(3) 0.46198(8) 0.6250(2) 0.0424(4) Uani 1 1 d . . . . .
H15 H 0.162056 0.468957 0.589437 0.051 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 C11 1.339(3) . ?
F2 C11 1.337(3) . ?
F3 C11 1.333(2) . ?
O1 C7 1.222(2) . ?
N1 C7 1.356(2) . ?
N1 C4 1.404(2) . ?
N1 C1 1.468(2) . ?
C1 C5 1.537(3) . ?
C1 C2 1.548(2) . ?
C2 C11 1.499(3) . ?
C2 C3 1.523(3) . ?
C3 C12 1.388(3) . ?
C3 C4 1.390(2) . ?
C4 C15 1.382(2) . ?
C5 C6 1.539(3) . ?
C5 C8 1.543(3) . ?
C5 C10 1.550(3) . ?
C6 C7 1.511(3) . ?
C8 C9 1.508(4) . ?
C9 C10 1.516(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C4 133.30(16) . . ?
C7 N1 C1 114.27(15) . . ?
C4 N1 C1 111.13(14) . . ?
N1 C1 C5 103.11(14) . . ?
N1 C1 C2 102.65(14) . . ?
C5 C1 C2 124.04(15) . . ?
C11 C2 C3 113.78(16) . . ?
C11 C2 C1 113.29(15) . . ?
C3 C2 C1 102.83(13) . . ?
C12 C3 C4 119.25(17) . . ?
C12 C3 C2 131.21(17) . . ?
C4 C3 C2 109.40(15) . . ?
C15 C4 C3 122.37(17) . . ?
C15 C4 N1 128.73(16) . . ?
C3 C4 N1 108.89(15) . . ?
C1 C5 C6 100.99(14) . . ?
C1 C5 C8 118.59(17) . . ?
C6 C5 C8 115.83(17) . . ?
C1 C5 C10 119.26(16) . . ?
C6 C5 C10 114.23(17) . . ?
C8 C5 C10 88.91(15) . . ?
C7 C6 C5 105.30(15) . . ?
O1 C7 N1 125.73(18) . . ?
O1 C7 C6 128.53(17) . . ?
N1 C7 C6 105.73(15) . . ?
C9 C8 C5 89.54(17) . . ?
C8 C9 C10 91.49(16) . . ?
C9 C10 C5 88.97(16) . . ?
F3 C11 F2 106.44(17) . . ?
F3 C11 F1 106.18(17) . . ?
F2 C11 F1 106.30(16) . . ?
F3 C11 C2 113.79(15) . . ?
F2 C11 C2 112.09(17) . . ?
F1 C11 C2 111.54(18) . . ?
C3 C12 C13 118.84(18) . . ?
C14 C13 C12 120.86(18) . . ?
C13 C14 C15 121.36(18) . . ?
C4 C15 C14 117.28(18) . . ?



####################################################################### 
# 
# 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_aml_273_f1
_database_code_depnum_ccdc_archive 'CCDC 2301768'
loop_
_audit_author_name
_audit_author_address
'Jeremy Forte'
;Sorbonne Universite, CNRS
France
;
_audit_update_record             
;
2023-10-17 deposited with the CCDC.	2023-12-28 downloaded from the CCDC.
;
_audit_creation_date             2023-10-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 F3 N O'
_chemical_formula_sum            'C18 H22 F3 N O'
_chemical_formula_weight         325.36
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0465(7)
_cell_length_b                   12.9285(12)
_cell_length_c                   16.1143(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1676.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3500
_cell_measurement_temperature    200
_cell_measurement_theta_max      24.01
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0420 before and 0.0385 after correction.
The Ratio of minimum to maximum transmission is 0.9631.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13483
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.419
_diffrn_reflns_theta_min         2.020
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3361
_reflns_number_total             4206
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.1603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          
;
Absolute structure cannot be determined with a Mo radiation. 
Only the relative configuration can be proved.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4495(2) 0.67246(11) 0.48789(8) 0.0569(4) Uani 1 1 d . . . . .
F2 F 0.6110(2) 0.77121(10) 0.41729(9) 0.0566(4) Uani 1 1 d . . . . .
F3 F 0.3606(2) 0.74546(11) 0.37679(10) 0.0615(4) Uani 1 1 d . . . . .
O1 O 0.4851(2) 0.25523(12) 0.34575(12) 0.0552(5) Uani 1 1 d . . . . .
N1 N 0.4937(2) 0.42774(13) 0.37919(11) 0.0316(4) Uani 1 1 d . . . . .
C1 C 0.6537(3) 0.44627(17) 0.41077(12) 0.0308(5) Uani 1 1 d . . . . .
C2 C 0.7622(3) 0.3770(2) 0.44720(15) 0.0435(6) Uani 1 1 d . . . . .
H2 H 0.733574 0.306119 0.453470 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9139(3) 0.4143(2) 0.47422(15) 0.0486(7) Uani 1 1 d . . . . .
H3 H 0.990474 0.368435 0.499861 0.058 Uiso 1 1 calc R U . . .
C4 C 0.9558(3) 0.5173(2) 0.46452(14) 0.0491(7) Uani 1 1 d . . . . .
H4 H 1.060869 0.541150 0.483406 0.059 Uiso 1 1 calc R U . . .
C5 C 0.8465(3) 0.5861(2) 0.42762(13) 0.0403(6) Uani 1 1 d . . . . .
H5 H 0.876297 0.656728 0.420679 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6933(3) 0.55050(17) 0.40101(12) 0.0299(5) Uani 1 1 d . . . . .
C7 C 0.5500(3) 0.60760(15) 0.35975(12) 0.0295(4) Uani 1 1 d . . . . .
H7 H 0.584094 0.631250 0.303175 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4927(3) 0.69867(17) 0.41032(14) 0.0414(6) Uani 1 1 d . . . . .
C9 C 0.4127(3) 0.52410(15) 0.35234(12) 0.0265(4) Uani 1 1 d . . . . .
H9 H 0.321297 0.541019 0.392140 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3349(2) 0.49527(15) 0.26725(12) 0.0262(4) Uani 1 1 d . . . . .
C11 C 0.2879(3) 0.38119(17) 0.28705(15) 0.0351(5) Uani 1 1 d . . . . .
H11A H 0.182036 0.377580 0.318200 0.042 Uiso 1 1 calc R U . . .
H11B H 0.277184 0.340092 0.235485 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4312(3) 0.34271(17) 0.33938(14) 0.0364(5) Uani 1 1 d . . . . .
C13 C 0.4705(2) 0.49540(16) 0.20033(12) 0.0300(4) Uani 1 1 d . . . . .
H13A H 0.494884 0.566782 0.183894 0.045 Uiso 1 1 calc R U . . .
H13B H 0.431794 0.456371 0.151903 0.045 Uiso 1 1 calc R U . . .
H13C H 0.571412 0.463112 0.222423 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1893(2) 0.56886(17) 0.24973(13) 0.0323(5) Uani 1 1 d . . . . .
H14A H 0.237995 0.638735 0.243327 0.039 Uiso 1 1 calc R U . . .
H14B H 0.121421 0.570684 0.300946 0.039 Uiso 1 1 calc R U . . .
C15 C 0.0665(3) 0.5546(2) 0.17692(14) 0.0388(5) Uani 1 1 d . . . . .
C16 C -0.0541(4) 0.6467(3) 0.18267(18) 0.0612(8) Uani 1 1 d . . . . .
H16A H -0.110613 0.645458 0.236544 0.092 Uiso 1 1 calc R U . . .
H16B H -0.136718 0.641751 0.138137 0.092 Uiso 1 1 calc R U . . .
H16C H 0.008059 0.711456 0.176983 0.092 Uiso 1 1 calc R U . . .
C17 C 0.1515(3) 0.5596(3) 0.09239(14) 0.0599(8) Uani 1 1 d . . . . .
H17A H 0.227597 0.618752 0.091023 0.090 Uiso 1 1 calc R U . . .
H17B H 0.067367 0.567573 0.048888 0.090 Uiso 1 1 calc R U . . .
H17C H 0.214147 0.495660 0.082978 0.090 Uiso 1 1 calc R U . . .
C18 C -0.0339(3) 0.4548(2) 0.1844(2) 0.0644(8) Uani 1 1 d . . . . .
H18A H 0.038263 0.395430 0.172835 0.097 Uiso 1 1 calc R U . . .
H18B H -0.125595 0.455938 0.144349 0.097 Uiso 1 1 calc R U . . .
H18C H -0.078803 0.448883 0.240707 0.097 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 C8 1.341(3) . ?
F2 C8 1.341(3) . ?
F3 C8 1.337(3) . ?
O1 C12 1.216(3) . ?
N1 C1 1.405(3) . ?
N1 C9 1.471(3) . ?
N1 C12 1.369(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C7 1.522(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.504(3) . ?
C7 C9 1.549(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.553(3) . ?
C10 C11 1.556(3) . ?
C10 C13 1.534(3) . ?
C10 C14 1.535(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.513(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.545(3) . ?
C15 C16 1.539(3) . ?
C15 C17 1.526(3) . ?
C15 C18 1.527(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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 C9 111.61(16) . . ?
C12 N1 C1 130.06(18) . . ?
C12 N1 C9 112.30(16) . . ?
C2 C1 N1 128.5(2) . . ?
C2 C1 C6 122.0(2) . . ?
C6 C1 N1 109.49(18) . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.7(2) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 110.19(18) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 130.4(2) . . ?
C6 C7 H7 109.8 . . ?
C6 C7 C9 103.65(16) . . ?
C8 C7 C6 112.02(17) . . ?
C8 C7 H7 109.8 . . ?
C8 C7 C9 111.65(18) . . ?
C9 C7 H7 109.8 . . ?
F1 C8 F2 106.43(19) . . ?
F1 C8 C7 112.75(18) . . ?
F2 C8 C7 112.1(2) . . ?
F3 C8 F1 106.5(2) . . ?
F3 C8 F2 106.35(18) . . ?
F3 C8 C7 112.24(19) . . ?
N1 C9 C7 104.55(16) . . ?
N1 C9 H9 108.8 . . ?
N1 C9 C10 103.60(15) . . ?
C7 C9 H9 108.8 . . ?
C7 C9 C10 121.51(16) . . ?
C10 C9 H9 108.8 . . ?
C9 C10 C11 98.31(16) . . ?
C13 C10 C9 109.52(16) . . ?
C13 C10 C11 108.55(16) . . ?
C13 C10 C14 114.38(17) . . ?
C14 C10 C9 108.73(15) . . ?
C14 C10 C11 116.07(17) . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 C10 103.93(17) . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
O1 C12 N1 125.2(2) . . ?
O1 C12 C11 128.7(2) . . ?
N1 C12 C11 106.10(18) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 106.4 . . ?
C10 C14 H14B 106.4 . . ?
C10 C14 C15 123.64(18) . . ?
H14A C14 H14B 106.5 . . ?
C15 C14 H14A 106.4 . . ?
C15 C14 H14B 106.4 . . ?
C16 C15 C14 105.4(2) . . ?
C17 C15 C14 112.70(18) . . ?
C17 C15 C16 107.7(2) . . ?
C17 C15 C18 110.1(2) . . ?
C18 C15 C14 112.3(2) . . ?
C18 C15 C16 108.4(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 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
N1 C1 C2 C3 -179.5(2) . . . . ?
N1 C1 C6 C5 -179.67(18) . . . . ?
N1 C1 C6 C7 0.0(2) . . . . ?
N1 C9 C10 C11 34.85(18) . . . . ?
N1 C9 C10 C13 -78.27(18) . . . . ?
N1 C9 C10 C14 156.09(15) . . . . ?
C1 N1 C9 C7 7.2(2) . . . . ?
C1 N1 C9 C10 135.41(16) . . . . ?
C1 N1 C12 O1 24.3(4) . . . . ?
C1 N1 C12 C11 -154.9(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C6 C7 C8 124.8(2) . . . . ?
C1 C6 C7 C9 4.3(2) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -179.6(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 179.4(2) . . . . ?
C5 C6 C7 C8 -55.6(3) . . . . ?
C5 C6 C7 C9 -176.1(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C7 C8 F1 -56.0(3) . . . . ?
C6 C7 C8 F2 64.1(2) . . . . ?
C6 C7 C8 F3 -176.34(18) . . . . ?
C6 C7 C9 N1 -6.65(19) . . . . ?
C6 C7 C9 C10 -123.01(18) . . . . ?
C7 C9 C10 C11 151.69(18) . . . . ?
C7 C9 C10 C13 38.6(2) . . . . ?
C7 C9 C10 C14 -87.1(2) . . . . ?
C8 C7 C9 N1 -127.41(18) . . . . ?
C8 C7 C9 C10 116.2(2) . . . . ?
C9 N1 C1 C2 174.8(2) . . . . ?
C9 N1 C1 C6 -4.7(2) . . . . ?
C9 N1 C12 O1 174.2(2) . . . . ?
C9 N1 C12 C11 -5.0(2) . . . . ?
C9 C7 C8 F1 59.7(3) . . . . ?
C9 C7 C8 F2 179.80(17) . . . . ?
C9 C7 C8 F3 -60.6(2) . . . . ?
C9 C10 C11 C12 -38.14(19) . . . . ?
C9 C10 C14 C15 -171.16(19) . . . . ?
C10 C11 C12 O1 -150.9(2) . . . . ?
C10 C11 C12 N1 28.2(2) . . . . ?
C10 C14 C15 C16 -178.8(2) . . . . ?
C10 C14 C15 C17 -61.6(3) . . . . ?
C10 C14 C15 C18 63.4(3) . . . . ?
C11 C10 C14 C15 -61.5(3) . . . . ?
C12 N1 C1 C2 -35.1(3) . . . . ?
C12 N1 C1 C6 145.3(2) . . . . ?
C12 N1 C9 C7 -148.38(17) . . . . ?
C12 N1 C9 C10 -20.2(2) . . . . ?
C13 C10 C11 C12 75.8(2) . . . . ?
C13 C10 C14 C15 66.1(3) . . . . ?
C14 C10 C11 C12 -153.78(18) . . . . ?

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

data_aml_56
_database_code_depnum_ccdc_archive 'CCDC 2295986'
loop_
_audit_author_name
_audit_author_address
'Jeremy Forte'
;Sorbonne Universite, CNRS
France
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-12-28 downloaded from the CCDC.
;
_audit_creation_date             2022-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 F3 N O'
_chemical_formula_sum            'C15 H16 F3 N O'
_chemical_formula_weight         283.29
_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 0.0181 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'
F F 0.0727 0.0534 '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'

_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                   9.2596(9)
_cell_length_b                   11.2829(10)
_cell_length_c                   13.4672(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.525(6)
_cell_angle_gamma                90
_cell_volume                     1368.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4292
_cell_measurement_temperature    199.98
_cell_measurement_theta_max      66.77
_cell_measurement_theta_min      4.91
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.446
_exptl_absorpt_coefficient_mu    0.974
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1477 before and 0.1044 after correction.
The Ratio of minimum to maximum transmission is 0.7554.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592

_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10750
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.238
_diffrn_reflns_theta_max         67.238
_diffrn_reflns_theta_min         4.912
_diffrn_ambient_temperature      199.98
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   micro-focus
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1971
_reflns_number_total             2417
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0062(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.2168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1055
_refine_special_details          ?

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.65812(14) 0.48544(10) 0.68658(8) 0.0591(4) Uani 1 1 d . . . . .
F2 F 0.84016(14) 0.42287(11) 0.80378(7) 0.0629(4) Uani 1 1 d . . . . .
F3 F 0.62620(15) 0.34386(11) 0.78595(8) 0.0681(4) Uani 1 1 d . . . . .
O1 O 0.87423(14) 0.39017(11) 0.34732(8) 0.0431(3) Uani 1 1 d . . . . .
N1 N 0.80609(14) 0.37634(12) 0.49922(9) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.90182(18) 0.36605(14) 0.43865(11) 0.0335(4) Uani 1 1 d . . . . .
C2 C 1.04706(18) 0.32217(17) 0.50428(13) 0.0413(4) Uani 1 1 d . . . . .
H2A H 1.118028 0.388398 0.524336 0.050 Uiso 1 1 calc R U . . .
H2B H 1.092286 0.261868 0.467532 0.050 Uiso 1 1 calc R U . . .
C3 C 1.00521(18) 0.26792(15) 0.59819(12) 0.0381(4) Uani 1 1 d . . . . .
C4 C 0.9562(2) 0.13929(16) 0.57500(14) 0.0471(5) Uani 1 1 d . . . . .
H4A H 0.927035 0.104987 0.634251 0.071 Uiso 1 1 calc R U . . .
H4B H 1.038652 0.093507 0.560216 0.071 Uiso 1 1 calc R U . . .
H4C H 0.871551 0.137041 0.515675 0.071 Uiso 1 1 calc R U . . .
C5 C 1.1300(2) 0.2744(2) 0.69455(14) 0.0588(6) Uani 1 1 d . . . . .
H5A H 1.161030 0.357071 0.707870 0.088 Uiso 1 1 calc R U . . .
H5B H 1.214502 0.227060 0.685181 0.088 Uiso 1 1 calc R U . . .
H5C H 1.094578 0.243319 0.752548 0.088 Uiso 1 1 calc R U . . .
C6 C 0.87317(17) 0.34882(14) 0.60657(11) 0.0320(4) Uani 1 1 d . . . . .
H6 H 0.913885 0.423738 0.641975 0.038 Uiso 1 1 calc R U . . .
C7 C 0.76043(18) 0.29634(14) 0.66213(11) 0.0339(4) Uani 1 1 d . . . . .
H7 H 0.811002 0.229170 0.704963 0.041 Uiso 1 1 calc R U . . .
C8 C 0.7206(2) 0.38645(16) 0.73397(12) 0.0442(4) Uani 1 1 d . . . . .
C9 C 0.62136(17) 0.24644(14) 0.59200(11) 0.0329(4) Uani 1 1 d . . . . .
C10 C 0.5496(2) 0.14916(15) 0.62178(12) 0.0399(4) Uani 1 1 d . . . . .
H10 H 0.588900 0.113128 0.686195 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4216(2) 0.10425(17) 0.55857(14) 0.0456(4) Uani 1 1 d . . . . .
H11 H 0.372863 0.038100 0.579770 0.055 Uiso 1 1 calc R U . . .
C12 C 0.36510(19) 0.15571(17) 0.46490(14) 0.0440(4) Uani 1 1 d . . . . .
H12 H 0.277370 0.124920 0.421276 0.053 Uiso 1 1 calc R U . . .
C13 C 0.43587(17) 0.25221(16) 0.43418(12) 0.0391(4) Uani 1 1 d . . . . .
H13 H 0.396403 0.287109 0.369306 0.047 Uiso 1 1 calc R U . . .
C14 C 0.56397(17) 0.29870(15) 0.49705(11) 0.0323(4) Uani 1 1 d . . . . .
C15 C 0.64836(17) 0.39924(15) 0.46330(12) 0.0355(4) Uani 1 1 d . . . . .
H15A H 0.622046 0.405384 0.387878 0.043 Uiso 1 1 calc R U . . .
H15B H 0.622335 0.474966 0.491912 0.043 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 C8 1.348(2) . ?
F2 C8 1.339(2) . ?
F3 C8 1.331(2) . ?
O1 C1 1.2268(19) . ?
N1 C1 1.343(2) . ?
N1 C6 1.4670(18) . ?
N1 C15 1.4503(19) . ?
C1 C2 1.510(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.534(2) . ?
C3 C4 1.531(3) . ?
C3 C5 1.524(2) . ?
C3 C6 1.551(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.538(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.508(2) . ?
C7 C9 1.516(2) . ?
C9 C10 1.390(2) . ?
C9 C14 1.395(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(2) . ?
C14 C15 1.507(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 113.13(12) . . ?
C1 N1 C15 124.69(12) . . ?
C15 N1 C6 121.85(13) . . ?
O1 C1 N1 125.29(15) . . ?
O1 C1 C2 127.43(15) . . ?
N1 C1 C2 107.27(13) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.56(13) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 C6 100.40(12) . . ?
C4 C3 C2 109.27(14) . . ?
C4 C3 C6 111.82(14) . . ?
C5 C3 C2 113.29(15) . . ?
C5 C3 C4 110.42(15) . . ?
C5 C3 C6 111.29(14) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C3 102.25(12) . . ?
N1 C6 H6 108.5 . . ?
N1 C6 C7 112.44(12) . . ?
C3 C6 H6 108.5 . . ?
C7 C6 C3 116.43(13) . . ?
C7 C6 H6 108.5 . . ?
C6 C7 H7 107.0 . . ?
C8 C7 C6 110.39(14) . . ?
C8 C7 H7 107.0 . . ?
C8 C7 C9 110.52(14) . . ?
C9 C7 C6 114.46(12) . . ?
C9 C7 H7 107.0 . . ?
F1 C8 C7 113.41(13) . . ?
F2 C8 F1 105.73(15) . . ?
F2 C8 C7 111.80(15) . . ?
F3 C8 F1 106.65(16) . . ?
F3 C8 F2 106.17(13) . . ?
F3 C8 C7 112.54(15) . . ?
C10 C9 C7 120.47(14) . . ?
C10 C9 C14 119.54(15) . . ?
C14 C9 C7 119.99(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.67(16) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.79(17) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.08(16) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.78(15) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C15 118.78(14) . . ?
C13 C14 C9 119.14(16) . . ?
C13 C14 C15 121.98(14) . . ?
N1 C15 C14 108.55(12) . . ?
N1 C15 H15A 110.0 . . ?
N1 C15 H15B 110.0 . . ?
C14 C15 H15A 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -161.46(16) . . . . ?
N1 C1 C2 C3 19.56(18) . . . . ?
N1 C6 C7 C8 -106.49(15) . . . . ?
N1 C6 C7 C9 18.96(19) . . . . ?
C1 N1 C6 C3 -23.82(17) . . . . ?
C1 N1 C6 C7 -149.45(14) . . . . ?
C1 N1 C15 C14 120.86(16) . . . . ?
C1 C2 C3 C4 85.45(16) . . . . ?
C1 C2 C3 C5 -150.98(15) . . . . ?
C1 C2 C3 C6 -32.23(16) . . . . ?
C2 C3 C6 N1 33.15(15) . . . . ?
C2 C3 C6 C7 156.12(13) . . . . ?
C3 C6 C7 C8 136.02(14) . . . . ?
C3 C6 C7 C9 -98.53(15) . . . . ?
C4 C3 C6 N1 -82.64(16) . . . . ?
C4 C3 C6 C7 40.33(18) . . . . ?
C5 C3 C6 N1 153.35(15) . . . . ?
C5 C3 C6 C7 -83.68(18) . . . . ?
C6 N1 C1 O1 -176.03(15) . . . . ?
C6 N1 C1 C2 2.98(18) . . . . ?
C6 N1 C15 C14 -52.11(19) . . . . ?
C6 C7 C8 F1 60.55(19) . . . . ?
C6 C7 C8 F2 -58.88(17) . . . . ?
C6 C7 C8 F3 -178.27(13) . . . . ?
C6 C7 C9 C10 147.15(15) . . . . ?
C6 C7 C9 C14 -33.3(2) . . . . ?
C7 C9 C10 C11 179.17(16) . . . . ?
C7 C9 C14 C13 -179.55(14) . . . . ?
C7 C9 C14 C15 4.2(2) . . . . ?
C8 C7 C9 C10 -87.47(18) . . . . ?
C8 C7 C9 C14 92.11(17) . . . . ?
C9 C7 C8 F1 -67.10(19) . . . . ?
C9 C7 C8 F2 173.47(13) . . . . ?
C9 C7 C8 F3 54.08(18) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C9 C14 C15 N1 36.0(2) . . . . ?
C10 C9 C14 C13 0.0(2) . . . . ?
C10 C9 C14 C15 -176.25(15) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C12 C13 C14 C15 176.44(15) . . . . ?
C13 C14 C15 N1 -140.15(15) . . . . ?
C14 C9 C10 C11 -0.4(2) . . . . ?
C15 N1 C1 O1 10.5(3) . . . . ?
C15 N1 C1 C2 -170.53(15) . . . . ?
C15 N1 C6 C3 149.90(14) . . . . ?
C15 N1 C6 C7 24.3(2) . . . . ?


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

data_pc_a
_database_code_depnum_ccdc_archive 'CCDC 2295987'
loop_
_audit_author_name
_audit_author_address
'Jeremy Forte'
;Sorbonne Universite, CNRS
France
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-12-28 downloaded from the CCDC.
;
_audit_creation_date             2022-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 F3 N O'
_chemical_formula_sum            'C14 H14 F3 N O'
_chemical_formula_weight         269.26
_chemical_absolute_configuration .
_chemical_melting_point          ?
_vrf_THETM01_pc_a                
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Because of a problem on our XRD machine, our beam intensity was lower 
than usual, but sufficient to solve correctly the crystal structure. Due to this 
lower intensity, data integration was carried out up to a resolution of 1.0 
Angstroms-1.
;
_vrf_PLAT089_pc_a                
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.18 Note  
RESPONSE: Same reason as above.
;
_vrf_PLAT340_pc_a                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01204 Ang.  
RESPONSE: Same reason as above.
;
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'
F F 0.0727 0.0534 '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'

_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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   14.7284(17)
_cell_length_b                   9.1741(8)
_cell_length_c                   9.7832(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.521(8)
_cell_angle_gamma                90
_cell_volume                     1307.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    823
_cell_measurement_temperature    200
_cell_measurement_theta_max      50.89
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.637
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.7502
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0836 after correction.
The Ratio of minimum to maximum transmission is 0.8524.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1376
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16063
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        51.869
_diffrn_reflns_theta_max         51.869
_diffrn_reflns_theta_min         4.820
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   micro-focus
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2240
_reflns_number_total             2890
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 854 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C20(H20), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.4080(4) 0.1395(6) 0.1397(7) 0.0815(18) Uani 1 1 d . . . . .
F2 F -0.3678(5) 0.0857(6) -0.0563(7) 0.093(2) Uani 1 1 d . . . . .
F3 F -0.2930(5) -0.0008(5) 0.1306(8) 0.092(2) Uani 1 1 d . . . . .
O1 O -0.1387(5) 0.6240(7) 0.3511(7) 0.0639(18) Uani 1 1 d . . . . .
N1 N -0.2253(5) 0.4392(6) 0.2384(7) 0.0420(16) Uani 1 1 d . . . . .
C1 C -0.1558(6) 0.4938(10) 0.3306(9) 0.046(2) Uani 1 1 d . . . . .
C2 C -0.1052(6) 0.3641(10) 0.4008(9) 0.055(2) Uani 1 1 d . . . . .
H2A H -0.125320 0.344577 0.491249 0.066 Uiso 1 1 calc R U . . .
H2B H -0.038083 0.381197 0.415522 0.066 Uiso 1 1 calc R U . . .
C3 C -0.1309(6) 0.2343(9) 0.2989(9) 0.050(2) Uani 1 1 d . . . . .
C4 C -0.0654(7) 0.2329(11) 0.1922(10) 0.065(3) Uani 1 1 d . . . . .
H4A H -0.068150 0.327129 0.144507 0.098 Uiso 1 1 calc R U . . .
H4B H -0.083257 0.155228 0.124787 0.098 Uiso 1 1 calc R U . . .
H4C H -0.002719 0.215530 0.238577 0.098 Uiso 1 1 calc R U . . .
C5 C -0.1280(9) 0.0913(11) 0.3774(15) 0.087(4) Uani 1 1 d . . . . .
H5A H -0.147472 0.011791 0.312823 0.131 Uiso 1 1 calc R U . . .
H5B H -0.169415 0.096812 0.446977 0.131 Uiso 1 1 calc R U . . .
H5C H -0.065250 0.073075 0.423195 0.131 Uiso 1 1 calc R U . . .
C6 C -0.2283(6) 0.2790(7) 0.2350(9) 0.0423(19) Uani 1 1 d . . . . .
H6 H -0.271806 0.245527 0.297847 0.051 Uiso 1 1 calc R U . . .
C7 C -0.2724(6) 0.2482(7) 0.0845(9) 0.044(2) Uani 1 1 d . . . . .
H7 H -0.222723 0.229432 0.027198 0.052 Uiso 1 1 calc R U . . .
C8 C -0.3359(7) 0.1200(9) 0.0738(11) 0.062(3) Uani 1 1 d . . . . .
C9 C -0.3196(5) 0.3914(8) 0.0395(8) 0.039(2) Uani 1 1 d . . . . .
C10 C -0.3839(6) 0.4247(9) -0.0744(8) 0.046(2) Uani 1 1 d . . . . .
H10 H -0.407678 0.351307 -0.138320 0.056 Uiso 1 1 calc R U . . .
C11 C -0.4126(7) 0.5679(10) -0.0922(10) 0.059(2) Uani 1 1 d . . . . .
H11 H -0.457020 0.592342 -0.169506 0.071 Uiso 1 1 calc R U . . .
C12 C -0.3787(7) 0.6762(9) -0.0011(10) 0.055(2) Uani 1 1 d . . . . .
H12 H -0.399829 0.773475 -0.016230 0.066 Uiso 1 1 calc R U . . .
C13 C -0.3139(6) 0.6440(8) 0.1123(9) 0.045(2) Uani 1 1 d . . . . .
H13 H -0.288983 0.718018 0.174784 0.054 Uiso 1 1 calc R U . . .
C14 C -0.2869(6) 0.4997(8) 0.1314(8) 0.038(2) Uani 1 1 d . . . . .
F4 F 0.2973(5) 0.9927(4) 0.2589(8) 0.094(2) Uani 1 1 d . . . . .
F5 F 0.3740(5) 0.8998(6) 0.1076(8) 0.095(2) Uani 1 1 d . . . . .
F6 F 0.4115(5) 0.8485(6) 0.3233(8) 0.0862(19) Uani 1 1 d . . . . .
O2 O 0.1343(4) 0.3769(7) 0.4171(7) 0.0613(17) Uani 1 1 d . . . . .
N2 N 0.2236(5) 0.5559(6) 0.3417(7) 0.0432(16) Uani 1 1 d . . . . .
C15 C 0.1526(6) 0.5045(10) 0.4026(9) 0.049(2) Uani 1 1 d . . . . .
C16 C 0.1044(7) 0.6380(9) 0.4477(10) 0.057(2) Uani 1 1 d . . . . .
H16A H 0.125070 0.659187 0.546610 0.068 Uiso 1 1 calc R U . . .
H16B H 0.037010 0.623623 0.433237 0.068 Uiso 1 1 calc R U . . .
C17 C 0.1314(6) 0.7639(9) 0.3554(9) 0.051(2) Uani 1 1 d . . . . .
C18 C 0.0668(7) 0.7669(11) 0.2187(10) 0.066(3) Uani 1 1 d . . . . .
H18A H 0.070820 0.674070 0.170337 0.099 Uiso 1 1 calc R U . . .
H18B H 0.084266 0.846726 0.161345 0.099 Uiso 1 1 calc R U . . .
H18C H 0.003657 0.781772 0.236339 0.099 Uiso 1 1 calc R U . . .
C19 C 0.1318(9) 0.9116(11) 0.4305(14) 0.084(4) Uani 1 1 d . . . . .
H19A H 0.070918 0.930153 0.455724 0.126 Uiso 1 1 calc R U . . .
H19B H 0.147372 0.989325 0.369230 0.126 Uiso 1 1 calc R U . . .
H19C H 0.177478 0.909328 0.514227 0.126 Uiso 1 1 calc R U . . .
C20 C 0.2297(6) 0.7162(7) 0.3374(9) 0.0433(19) Uani 1 1 d . . . . .
H20 H 0.273093 0.749797 0.419797 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2745(6) 0.7433(7) 0.2062(9) 0.044(2) Uani 1 1 d . . . . .
H21 H 0.225606 0.762131 0.125715 0.053 Uiso 1 1 calc R U . . .
C22 C 0.3406(8) 0.8690(10) 0.2235(12) 0.067(3) Uani 1 1 d . . . . .
C23 C 0.3211(6) 0.5979(8) 0.1861(8) 0.041(2) Uani 1 1 d . . . . .
C24 C 0.3839(6) 0.5595(9) 0.1019(9) 0.049(2) Uani 1 1 d . . . . .
H24 H 0.408278 0.630976 0.047162 0.059 Uiso 1 1 calc R U . . .
C25 C 0.4115(6) 0.4141(9) 0.0976(9) 0.051(2) Uani 1 1 d . . . . .
H25 H 0.456500 0.387332 0.041957 0.061 Uiso 1 1 calc R U . . .
C26 C 0.3742(6) 0.3088(8) 0.1733(10) 0.049(2) Uani 1 1 d . . . . .
H26 H 0.392432 0.210069 0.166864 0.059 Uiso 1 1 calc R U . . .
C27 C 0.3103(6) 0.3452(8) 0.2588(8) 0.043(2) Uani 1 1 d . . . . .
H27 H 0.284854 0.272947 0.311478 0.051 Uiso 1 1 calc R U . . .
C28 C 0.2848(6) 0.4904(7) 0.2647(8) 0.038(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.334(12) . ?
F2 C8 1.328(13) . ?
F3 C8 1.353(12) . ?
O1 C1 1.231(11) . ?
N1 C1 1.355(12) . ?
N1 C6 1.471(9) . ?
N1 C14 1.395(12) . ?
C1 C2 1.514(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.564(14) . ?
C3 C4 1.523(13) . ?
C3 C5 1.518(13) . ?
C3 C6 1.533(13) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.544(12) . ?
C7 H7 1.0000 . ?
C7 C8 1.496(13) . ?
C7 C9 1.521(12) . ?
C9 C10 1.385(12) . ?
C9 C14 1.379(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(14) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(13) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(11) . ?
F4 C22 1.371(13) . ?
F5 C22 1.331(13) . ?
F6 C22 1.333(13) . ?
O2 C15 1.214(11) . ?
N2 C15 1.363(12) . ?
N2 C20 1.474(9) . ?
N2 C28 1.393(11) . ?
C15 C16 1.514(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.553(14) . ?
C17 C18 1.523(13) . ?
C17 C19 1.541(13) . ?
C17 C20 1.547(12) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 1.0000 . ?
C20 C21 1.548(12) . ?
C21 H21 1.0000 . ?
C21 C22 1.503(13) . ?
C21 C23 1.525(12) . ?
C23 C24 1.373(13) . ?
C23 C28 1.404(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.398(13) . ?
C25 H25 0.9500 . ?
C25 C26 1.379(13) . ?
C26 H26 0.9500 . ?
C26 C27 1.389(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(11) . ?

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 C6 113.7(7) . . ?
C1 N1 C14 134.0(6) . . ?
C14 N1 C6 111.5(7) . . ?
O1 C1 N1 125.6(8) . . ?
O1 C1 C2 127.9(9) . . ?
N1 C1 C2 106.5(7) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.6(7) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C4 C3 C2 109.0(8) . . ?
C4 C3 C6 111.9(7) . . ?
C5 C3 C2 110.4(8) . . ?
C5 C3 C4 111.5(9) . . ?
C5 C3 C6 113.1(8) . . ?
C6 C3 C2 100.4(7) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C3 103.6(7) . . ?
N1 C6 H6 108.2 . . ?
N1 C6 C7 102.2(6) . . ?
C3 C6 H6 108.2 . . ?
C3 C6 C7 125.1(6) . . ?
C7 C6 H6 108.2 . . ?
C6 C7 H7 109.1 . . ?
C8 C7 C6 112.4(7) . . ?
C8 C7 H7 109.1 . . ?
C8 C7 C9 113.8(7) . . ?
C9 C7 C6 103.1(6) . . ?
C9 C7 H7 109.1 . . ?
F1 C8 F3 105.6(8) . . ?
F1 C8 C7 113.3(7) . . ?
F2 C8 F1 107.5(9) . . ?
F2 C8 F3 106.1(7) . . ?
F2 C8 C7 112.5(8) . . ?
F3 C8 C7 111.5(9) . . ?
C10 C9 C7 130.7(7) . . ?
C14 C9 C7 109.5(7) . . ?
C14 C9 C10 119.8(7) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.1(8) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(9) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(8) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 121.3 . . ?
C12 C13 C14 117.5(8) . . ?
C14 C13 H13 121.3 . . ?
C9 C14 N1 109.2(6) . . ?
C9 C14 C13 122.3(8) . . ?
C13 C14 N1 128.5(8) . . ?
C15 N2 C20 114.3(7) . . ?
C15 N2 C28 133.4(6) . . ?
C28 N2 C20 111.6(6) . . ?
O2 C15 N2 125.7(8) . . ?
O2 C15 C16 128.6(8) . . ?
N2 C15 C16 105.7(7) . . ?
C15 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C15 C16 C17 105.1(8) . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C18 C17 C16 110.1(8) . . ?
C18 C17 C19 111.1(9) . . ?
C18 C17 C20 112.3(7) . . ?
C19 C17 C16 111.1(8) . . ?
C19 C17 C20 111.4(8) . . ?
C20 C17 C16 100.4(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C17 102.5(6) . . ?
N2 C20 H20 108.6 . . ?
N2 C20 C21 102.6(6) . . ?
C17 C20 H20 108.6 . . ?
C17 C20 C21 124.8(7) . . ?
C21 C20 H20 108.6 . . ?
C20 C21 H21 109.6 . . ?
C22 C21 C20 112.2(7) . . ?
C22 C21 H21 109.6 . . ?
C22 C21 C23 112.9(8) . . ?
C23 C21 C20 102.8(6) . . ?
C23 C21 H21 109.6 . . ?
F4 C22 C21 110.2(9) . . ?
F5 C22 F4 106.5(7) . . ?
F5 C22 F6 107.8(10) . . ?
F5 C22 C21 112.4(9) . . ?
F6 C22 F4 105.9(9) . . ?
F6 C22 C21 113.5(8) . . ?
C24 C23 C21 131.1(7) . . ?
C24 C23 C28 119.6(7) . . ?
C28 C23 C21 109.2(7) . . ?
C23 C24 H24 120.4 . . ?
C23 C24 C25 119.2(8) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.7(8) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 121.0(7) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 121.1 . . ?
C28 C27 C26 117.9(7) . . ?
C28 C27 H27 121.1 . . ?
N2 C28 C23 108.8(6) . . ?
C27 C28 N2 129.6(7) . . ?
C27 C28 C23 121.6(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -158.8(8) . . . . ?
N1 C1 C2 C3 21.2(8) . . . . ?
N1 C6 C7 C8 -143.1(7) . . . . ?
N1 C6 C7 C9 -20.1(7) . . . . ?
C1 N1 C6 C3 -20.3(9) . . . . ?
C1 N1 C6 C7 -151.4(7) . . . . ?
C1 N1 C14 C9 157.8(8) . . . . ?
C1 N1 C14 C13 -21.8(14) . . . . ?
C1 C2 C3 C4 85.8(8) . . . . ?
C1 C2 C3 C5 -151.4(8) . . . . ?
C1 C2 C3 C6 -31.8(8) . . . . ?
C2 C3 C6 N1 30.8(8) . . . . ?
C2 C3 C6 C7 146.6(7) . . . . ?
C3 C6 C7 C8 100.4(9) . . . . ?
C3 C6 C7 C9 -136.6(7) . . . . ?
C4 C3 C6 N1 -84.7(8) . . . . ?
C4 C3 C6 C7 31.2(11) . . . . ?
C5 C3 C6 N1 148.4(9) . . . . ?
C5 C3 C6 C7 -95.7(10) . . . . ?
C6 N1 C1 O1 179.2(8) . . . . ?
C6 N1 C1 C2 -0.8(9) . . . . ?
C6 N1 C14 C9 -11.2(9) . . . . ?
C6 N1 C14 C13 169.3(8) . . . . ?
C6 C7 C8 F1 63.2(10) . . . . ?
C6 C7 C8 F2 -174.7(7) . . . . ?
C6 C7 C8 F3 -55.7(10) . . . . ?
C6 C7 C9 C10 -166.7(8) . . . . ?
C6 C7 C9 C14 15.1(8) . . . . ?
C7 C9 C10 C11 -177.4(8) . . . . ?
C7 C9 C14 N1 -3.2(8) . . . . ?
C7 C9 C14 C13 176.4(7) . . . . ?
C8 C7 C9 C10 -44.7(12) . . . . ?
C8 C7 C9 C14 137.1(7) . . . . ?
C9 C7 C8 F1 -53.6(11) . . . . ?
C9 C7 C8 F2 68.5(10) . . . . ?
C9 C7 C8 F3 -172.5(8) . . . . ?
C9 C10 C11 C12 0.4(12) . . . . ?
C10 C9 C14 N1 178.4(6) . . . . ?
C10 C9 C14 C13 -2.0(11) . . . . ?
C10 C11 C12 C13 0.1(13) . . . . ?
C11 C12 C13 C14 -1.4(12) . . . . ?
C12 C13 C14 N1 -178.1(8) . . . . ?
C12 C13 C14 C9 2.4(11) . . . . ?
C14 N1 C1 O1 10.5(14) . . . . ?
C14 N1 C1 C2 -169.5(8) . . . . ?
C14 N1 C6 C3 151.1(6) . . . . ?
C14 N1 C6 C7 19.9(8) . . . . ?
C14 C9 C10 C11 0.6(11) . . . . ?
O2 C15 C16 C17 -158.6(9) . . . . ?
N2 C15 C16 C17 22.0(9) . . . . ?
N2 C20 C21 C22 -142.9(7) . . . . ?
N2 C20 C21 C23 -21.3(8) . . . . ?
C15 N2 C20 C17 -20.5(9) . . . . ?
C15 N2 C20 C21 -150.9(7) . . . . ?
C15 N2 C28 C23 158.6(8) . . . . ?
C15 N2 C28 C27 -21.3(15) . . . . ?
C15 C16 C17 C18 85.5(9) . . . . ?
C15 C16 C17 C19 -151.0(8) . . . . ?
C15 C16 C17 C20 -33.0(9) . . . . ?
C16 C17 C20 N2 31.5(8) . . . . ?
C16 C17 C20 C21 146.7(7) . . . . ?
C17 C20 C21 C22 101.9(10) . . . . ?
C17 C20 C21 C23 -136.5(7) . . . . ?
C18 C17 C20 N2 -85.4(9) . . . . ?
C18 C17 C20 C21 29.8(11) . . . . ?
C19 C17 C20 N2 149.2(8) . . . . ?
C19 C17 C20 C21 -95.6(10) . . . . ?
C20 N2 C15 O2 179.8(9) . . . . ?
C20 N2 C15 C16 -0.8(10) . . . . ?
C20 N2 C28 C23 -10.9(9) . . . . ?
C20 N2 C28 C27 169.2(8) . . . . ?
C20 C21 C22 F4 -56.5(11) . . . . ?
C20 C21 C22 F5 -175.2(8) . . . . ?
C20 C21 C22 F6 62.1(11) . . . . ?
C20 C21 C23 C24 -168.0(9) . . . . ?
C20 C21 C23 C28 16.5(9) . . . . ?
C21 C23 C24 C25 -176.0(8) . . . . ?
C21 C23 C28 N2 -4.3(9) . . . . ?
C21 C23 C28 C27 175.6(8) . . . . ?
C22 C21 C23 C24 -46.9(13) . . . . ?
C22 C21 C23 C28 137.6(8) . . . . ?
C23 C21 C22 F4 -172.1(8) . . . . ?
C23 C21 C22 F5 69.2(10) . . . . ?
C23 C21 C22 F6 -53.5(12) . . . . ?
C23 C24 C25 C26 2.1(13) . . . . ?
C24 C23 C28 N2 179.6(8) . . . . ?
C24 C23 C28 C27 -0.5(12) . . . . ?
C24 C25 C26 C27 -1.9(14) . . . . ?
C25 C26 C27 C28 0.5(13) . . . . ?
C26 C27 C28 N2 -179.4(8) . . . . ?
C26 C27 C28 C23 0.7(12) . . . . ?
C28 N2 C15 O2 10.5(15) . . . . ?
C28 N2 C15 C16 -170.1(8) . . . . ?
C28 N2 C20 C17 151.1(7) . . . . ?
C28 N2 C20 C21 20.7(9) . . . . ?
C28 C23 C24 C25 -0.9(12) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
