# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_d8v21586
_database_code_depnum_ccdc_archive 'CCDC 2123735'
loop_
_audit_author_name
_audit_author_address
ShiJi
;Donghua University
China
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 F6 N O4'
_chemical_formula_weight         387.28

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

_space_group_crystal_system      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                   16.8153(11)
_cell_length_b                   8.7366(5)
_cell_length_c                   12.2243(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.655(2)
_cell_angle_gamma                90
_cell_volume                     1752.23(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7338
_cell_measurement_theta_min      5.283
_cell_measurement_theta_max      50.549

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19678
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3424
_reflns_number_gt                2634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.4112P] 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     SHELXL
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3424
_refine_ls_number_parameters     266
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_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
F1 F 0.86455(10) 0.32702(17) 0.31203(10) 0.0996(5) Uani 1 1 d . . . . .
F2 F 0.92383(9) 0.11982(16) 0.37557(15) 0.1112(5) Uani 1 1 d . . . . .
F3 F 0.79868(8) 0.15623(15) 0.37918(12) 0.0941(4) Uani 1 1 d . . . . .
F4 F 0.4643(4) -0.0285(8) 0.7291(4) 0.1122(16) Uani 0.5 1 d . U P A 1
F5 F 0.3808(6) 0.0434(7) 0.5797(8) 0.1013(18) Uani 0.5 1 d . U P A 1
F6 F 0.4111(4) 0.1917(8) 0.7201(5) 0.1174(18) Uani 0.5 1 d . U P A 1
F4' F 0.4490(4) -0.0648(7) 0.6766(5) 0.1178(16) Uani 0.5 1 d . U P A 2
F5' F 0.3694(5) 0.1022(8) 0.5902(8) 0.115(2) Uani 0.5 1 d . U P A 2
F6' F 0.4295(4) 0.1406(9) 0.7560(4) 0.1058(17) Uani 0.5 1 d . U P A 2
O1 O 0.69285(8) 0.46789(18) 0.43382(12) 0.0824(5) Uani 1 1 d . . . . .
O2 O 0.77828(7) 0.33737(13) 0.57039(10) 0.0562(3) Uani 1 1 d . . . . .
O3 O 0.93579(8) 0.59563(14) 0.56877(12) 0.0714(4) Uani 1 1 d . . . . .
O4 O 0.82049(7) 0.60316(14) 0.63639(10) 0.0613(4) Uani 1 1 d . . . . .
N1 N 0.84267(8) 0.40710(16) 0.52991(12) 0.0571(4) Uani 1 1 d . . . . .
C1 C 0.87231(10) 0.5436(2) 0.58153(14) 0.0546(4) Uani 1 1 d . . . . .
C2 C 0.89902(11) 0.2936(2) 0.50683(15) 0.0581(4) Uani 1 1 d . . . . .
H2A H 0.9051 0.2134 0.5629 0.070 Uiso 1 1 calc R U . . .
H2B H 0.9520 0.3405 0.5118 0.070 Uiso 1 1 calc R U . . .
C3 C 0.87071(12) 0.2250(2) 0.39354(18) 0.0692(5) Uani 1 1 d . . . . .
C4 C 0.83418(11) 0.75888(19) 0.68693(15) 0.0584(4) Uani 1 1 d . . . . .
C5 C 0.91216(14) 0.7597(3) 0.77582(17) 0.0782(6) Uani 1 1 d . . . . .
H5A H 0.9100 0.6809 0.8298 0.117 Uiso 1 1 calc R U . . .
H5B H 0.9186 0.8574 0.8126 0.117 Uiso 1 1 calc R U . . .
H5C H 0.9575 0.7414 0.7416 0.117 Uiso 1 1 calc R U . . .
C6 C 0.83473(16) 0.8750(3) 0.59598(19) 0.0847(6) Uani 1 1 d . . . . .
H6A H 0.8833 0.8627 0.5678 0.127 Uiso 1 1 calc R U . . .
H6B H 0.8334 0.9762 0.6260 0.127 Uiso 1 1 calc R U . . .
H6C H 0.7878 0.8599 0.5362 0.127 Uiso 1 1 calc R U . . .
C7 C 0.76069(14) 0.7778(3) 0.7377(2) 0.0907(7) Uani 1 1 d . . . . .
H7A H 0.7121 0.7766 0.6793 0.136 Uiso 1 1 calc R U . . .
H7B H 0.7644 0.8734 0.7772 0.136 Uiso 1 1 calc R U . . .
H7C H 0.7588 0.6953 0.7890 0.136 Uiso 1 1 calc R U . . .
C8 C 0.70304(10) 0.3789(2) 0.50933(14) 0.0555(4) Uani 1 1 d . . . . .
C9 C 0.63761(10) 0.29894(18) 0.55144(13) 0.0511(4) Uani 1 1 d . . . . .
C10 C 0.65268(10) 0.1970(2) 0.63990(15) 0.0585(4) Uani 1 1 d . . . . .
H10 H 0.7060 0.1760 0.6768 0.070 Uiso 1 1 calc R U . . .
C11 C 0.58867(11) 0.1260(2) 0.67373(15) 0.0634(5) Uani 1 1 d . . . . .
H11 H 0.5989 0.0570 0.7331 0.076 Uiso 1 1 calc R U . . .
C12 C 0.50968(10) 0.1578(2) 0.61946(14) 0.0571(4) Uani 1 1 d . . . . .
C13 C 0.49424(11) 0.2589(2) 0.53121(17) 0.0722(6) Uani 1 1 d . . . . .
H13 H 0.4409 0.2799 0.4945 0.087 Uiso 1 1 calc R U . . .
C14 C 0.55823(11) 0.3288(2) 0.49750(17) 0.0694(5) Uani 1 1 d . . . . .
H14 H 0.5478 0.3970 0.4376 0.083 Uiso 1 1 calc R U . . .
C15 C 0.44023(12) 0.0871(3) 0.65975(19) 0.0745(6) 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 C3 1.324(2) . ?
F2 C3 1.333(2) . ?
F3 C3 1.329(2) . ?
F4 C15 1.324(6) . ?
F5 C15 1.294(9) . ?
F6 C15 1.333(7) . ?
F4' C15 1.346(7) . ?
F5' C15 1.309(9) . ?
F6' C15 1.314(7) . ?
O1 C8 1.190(2) . ?
O2 C8 1.370(2) . ?
O2 N1 1.4224(17) . ?
O3 C1 1.2013(19) . ?
O4 C1 1.3176(19) . ?
O4 C4 1.491(2) . ?
N1 C1 1.390(2) . ?
N1 C2 1.442(2) . ?
C2 C3 1.488(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C6 1.506(3) . ?
C4 C7 1.508(3) . ?
C4 C5 1.509(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.487(2) . ?
C9 C14 1.378(2) . ?
C9 C10 1.381(2) . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C12 C15 1.497(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C8 O2 N1 112.30(12) . . ?
C1 O4 C4 120.80(13) . . ?
C1 N1 O2 115.74(13) . . ?
C1 N1 C2 119.58(14) . . ?
O2 N1 C2 110.88(13) . . ?
O3 C1 O4 128.47(16) . . ?
O3 C1 N1 120.42(15) . . ?
O4 C1 N1 111.02(14) . . ?
N1 C2 C3 111.65(15) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
F1 C3 F3 106.64(18) . . ?
F1 C3 F2 106.55(17) . . ?
F3 C3 F2 106.88(15) . . ?
F1 C3 C2 112.72(15) . . ?
F3 C3 C2 113.66(17) . . ?
F2 C3 C2 109.97(17) . . ?
O4 C4 C6 109.50(15) . . ?
O4 C4 C7 101.79(15) . . ?
C6 C4 C7 111.60(18) . . ?
O4 C4 C5 109.50(15) . . ?
C6 C4 C5 112.54(17) . . ?
C7 C4 C5 111.36(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 O2 123.69(16) . . ?
O1 C8 C9 125.71(16) . . ?
O2 C8 C9 110.59(14) . . ?
C14 C9 C10 119.29(16) . . ?
C14 C9 C8 117.24(15) . . ?
C10 C9 C8 123.47(15) . . ?
C9 C10 C11 120.16(16) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.87(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.28(16) . . ?
C13 C12 C15 119.79(17) . . ?
C11 C12 C15 119.88(17) . . ?
C12 C13 C14 119.65(17) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 120.75(17) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
F5' C15 F6' 105.2(5) . . ?
F5 C15 F4 109.6(5) . . ?
F5 C15 F6 107.7(5) . . ?
F4 C15 F6 105.4(4) . . ?
F5' C15 F4' 104.6(5) . . ?
F6' C15 F4' 104.2(4) . . ?
F5 C15 C12 113.7(5) . . ?
F5' C15 C12 114.1(5) . . ?
F6' C15 C12 114.7(4) . . ?
F4 C15 C12 112.0(3) . . ?
F6 C15 C12 107.9(4) . . ?
F4' C15 C12 113.0(3) . . ?

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
C8 O2 N1 C1 93.56(16) . . . . ?
C8 O2 N1 C2 -126.05(15) . . . . ?
C4 O4 C1 O3 4.0(3) . . . . ?
C4 O4 C1 N1 -172.52(14) . . . . ?
O2 N1 C1 O3 165.81(16) . . . . ?
C2 N1 C1 O3 29.0(2) . . . . ?
O2 N1 C1 O4 -17.4(2) . . . . ?
C2 N1 C1 O4 -154.16(15) . . . . ?
C1 N1 C2 C3 -137.46(16) . . . . ?
O2 N1 C2 C3 83.87(17) . . . . ?
N1 C2 C3 F1 61.8(2) . . . . ?
N1 C2 C3 F3 -59.7(2) . . . . ?
N1 C2 C3 F2 -179.43(15) . . . . ?
C1 O4 C4 C6 61.0(2) . . . . ?
C1 O4 C4 C7 179.23(17) . . . . ?
C1 O4 C4 C5 -62.8(2) . . . . ?
N1 O2 C8 O1 -2.7(2) . . . . ?
N1 O2 C8 C9 177.75(12) . . . . ?
O1 C8 C9 C14 0.9(3) . . . . ?
O2 C8 C9 C14 -179.64(15) . . . . ?
O1 C8 C9 C10 -179.71(18) . . . . ?
O2 C8 C9 C10 -0.2(2) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 -179.47(16) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C10 C11 C12 C15 -176.90(18) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C15 C12 C13 C14 177.17(19) . . . . ?
C12 C13 C14 C9 -0.2(3) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
C8 C9 C14 C13 179.76(18) . . . . ?
C13 C12 C15 F5 42.6(4) . . . . ?
C11 C12 C15 F5 -140.0(4) . . . . ?
C13 C12 C15 F5' 14.7(4) . . . . ?
C11 C12 C15 F5' -167.9(4) . . . . ?
C13 C12 C15 F6' -106.7(4) . . . . ?
C11 C12 C15 F6' 70.7(4) . . . . ?
C13 C12 C15 F4 167.5(3) . . . . ?
C11 C12 C15 F4 -15.1(4) . . . . ?
C13 C12 C15 F6 -76.9(4) . . . . ?
C11 C12 C15 F6 100.5(4) . . . . ?
C13 C12 C15 F4' 134.0(3) . . . . ?
C11 C12 C15 F4' -48.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A O3 0.96 2.49 3.033(3) 115.5 .
C5 H5C O3 0.96 2.43 3.010(2) 119.0 .
C2 H2B O3 0.97 2.38 3.261(2) 150.9 3_766
C2 H2B O3 0.97 2.38 3.261(2) 150.9 3_766
C5 H5C O3 0.96 2.43 3.010(2) 119.0 .
C6 H6A O3 0.96 2.49 3.033(3) 115.5 .
C2 H2B O3 0.97 2.38 3.261(2) 150.9 3_766
C5 H5C O3 0.96 2.43 3.010(2) 119.0 .
C6 H6A O3 0.96 2.49 3.033(3) 115.5 .
C2 H2B O3 0.97 2.38 3.261(2) 150.9 3_766
C5 H5C O3 0.96 2.43 3.010(2) 119.0 .
C6 H6A O3 0.96 2.49 3.033(3) 115.5 .
C2 H2B O3 0.97 2.38 3.261(2) 150.9 3_766
C5 H5C O3 0.96 2.43 3.010(2) 119.0 .
C6 H6A O3 0.96 2.49 3.033(3) 115.5 .
C2 H2B O3 0.97 2.38 3.261(2) 150.9 3_766
C5 H5C O3 0.96 2.43 3.010(2) 119.0 .
C6 H6A O3 0.96 2.49 3.033(3) 115.5 .

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v21442
_database_code_depnum_ccdc_archive 'CCDC 2123736'
loop_
_audit_author_name
_audit_author_address
chanwu
;Donghua University
China
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 F3 N2 O2'
_chemical_formula_weight         328.33

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.5525(15)
_cell_length_b                   38.111(5)
_cell_length_c                   9.0256(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.355(4)
_cell_angle_gamma                90
_cell_volume                     3500.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      4.801
_cell_measurement_theta_max      43.722

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51834
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             6155
_reflns_number_gt                3521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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     SHELXL
_refine_ls_extinction_coef       0.019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6155
_refine_ls_number_parameters     424
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1664
_refine_ls_R_factor_gt           0.1180
_refine_ls_wR_factor_ref         0.3998
_refine_ls_wR_factor_gt          0.3480
_refine_ls_goodness_of_fit_ref   1.414
_refine_ls_restrained_S_all      1.416
_refine_ls_shift/su_max          0.002
_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
F1 F 0.2526(4) 0.46964(9) 0.1784(4) 0.1266(12) Uani 1 1 d . . . . .
F2 F 0.4236(4) 0.46840(9) 0.3682(4) 0.1258(13) Uani 1 1 d . . . . .
F3 F 0.2652(3) 0.50192(9) 0.3720(4) 0.1143(11) Uani 1 1 d . . . . .
O1 O 0.3274(4) 0.51362(10) -0.1035(4) 0.0995(12) Uani 1 1 d . . . . .
O2 O 0.1988(3) 0.56148(8) -0.1157(3) 0.0875(10) Uani 1 1 d . . . . .
N1 N 0.1362(3) 0.57563(9) 0.1840(4) 0.0637(9) Uani 1 1 d . . . . .
N2 N 0.3021(3) 0.54062(9) 0.1124(4) 0.0684(10) Uani 1 1 d . . . . .
C1 C 0.1282(4) 0.60802(11) 0.2488(5) 0.0650(11) Uani 1 1 d . . . . .
C2 C 0.0208(5) 0.62478(13) 0.2779(5) 0.0835(13) Uani 1 1 d . . . . .
H2 H -0.0620 0.6145 0.2518 0.100 Uiso 1 1 calc R U . . .
C3 C 0.0408(6) 0.65681(16) 0.3458(7) 0.1042(18) Uani 1 1 d . . . . .
H3 H -0.0297 0.6685 0.3670 0.125 Uiso 1 1 calc R U . . .
C4 C 0.1627(7) 0.67248(15) 0.3841(7) 0.1073(18) Uani 1 1 d . . . . .
H4 H 0.1733 0.6942 0.4324 0.129 Uiso 1 1 calc R U . . .
C5 C 0.2694(6) 0.65640(15) 0.3519(7) 0.1070(18) Uani 1 1 d . . . . .
H5 H 0.3508 0.6675 0.3759 0.128 Uiso 1 1 calc R U . . .
C6 C 0.2541(4) 0.62363(12) 0.2837(5) 0.0742(12) Uani 1 1 d . . . . .
C7 C 0.3369(4) 0.59969(12) 0.2350(5) 0.0746(12) Uani 1 1 d . . . . .
H7 H 0.4259 0.6028 0.2434 0.089 Uiso 1 1 calc R U . . .
C8 C 0.2646(4) 0.57141(12) 0.1742(4) 0.0657(11) Uani 1 1 d . . . . .
C9 C 0.0268(5) 0.55224(13) 0.1236(6) 0.0883(14) Uani 1 1 d . . . . .
H9A H -0.0284 0.5619 0.0304 0.132 Uiso 1 1 calc R U . . .
H9B H -0.0231 0.5496 0.1977 0.132 Uiso 1 1 calc R U . . .
H9C H 0.0593 0.5298 0.1026 0.132 Uiso 1 1 calc R U . . .
C10 C 0.3981(4) 0.51739(12) 0.2115(5) 0.0731(12) Uani 1 1 d . . . . .
H10A H 0.4559 0.5312 0.2920 0.088 Uiso 1 1 calc R U . . .
H10B H 0.4513 0.5065 0.1515 0.088 Uiso 1 1 calc R U . . .
C11 C 0.3352(5) 0.48959(14) 0.2825(6) 0.0839(14) Uani 1 1 d . . . . .
C12 C 0.2801(4) 0.53696(13) -0.0458(5) 0.0740(12) Uani 1 1 d . . . . .
C13 C 0.1618(5) 0.56567(13) -0.2838(5) 0.0829(14) Uani 1 1 d . . . . .
C14 C 0.0877(7) 0.53407(17) -0.3568(7) 0.123(2) Uani 1 1 d . . . . .
H14A H 0.1451 0.5141 -0.3394 0.185 Uiso 1 1 calc R U . . .
H14B H 0.0544 0.5380 -0.4652 0.185 Uiso 1 1 calc R U . . .
H14C H 0.0157 0.5298 -0.3126 0.185 Uiso 1 1 calc R U . . .
C15 C 0.2823(8) 0.5717(2) -0.3401(9) 0.147(3) Uani 1 1 d . . . . .
H15A H 0.3264 0.5926 -0.2935 0.220 Uiso 1 1 calc R U . . .
H15B H 0.2569 0.5744 -0.4498 0.220 Uiso 1 1 calc R U . . .
H15C H 0.3405 0.5520 -0.3129 0.220 Uiso 1 1 calc R U . . .
C16 C 0.0750(8) 0.59741(18) -0.3076(7) 0.132(3) Uani 1 1 d . . . . .
H16A H 0.0008 0.5930 -0.2677 0.198 Uiso 1 1 calc R U . . .
H16B H 0.0451 0.6025 -0.4154 0.198 Uiso 1 1 calc R U . . .
H16C H 0.1237 0.6171 -0.2549 0.198 Uiso 1 1 calc R U . . .
F4 F 0.7269(6) 0.2700(2) 0.2075(12) 0.280(4) Uani 1 1 d . . . . .
F5 F 0.6559(6) 0.3187(3) 0.1414(12) 0.269(4) Uani 1 1 d . . . . .
F6 F 0.5880(9) 0.2925(5) 0.2800(18) 0.358(8) Uani 1 1 d . . . . .
O3 O 0.3165(7) 0.25818(17) 0.1897(10) 0.195(3) Uani 1 1 d . . . . .
O4 O 0.1944(4) 0.30444(10) 0.0856(5) 0.1070(13) Uani 1 1 d . . . . .
N3 N 0.3688(4) 0.35912(14) -0.0017(7) 0.1085(15) Uani 1 1 d . . . . .
N4 N 0.3896(6) 0.29715(15) 0.0444(8) 0.141(2) Uani 1 1 d . . . . .
C17 C 0.3429(4) 0.38197(15) -0.1302(7) 0.0878(15) Uani 1 1 d . . . . .
C18 C 0.3275(5) 0.41914(16) -0.1438(9) 0.1045(19) Uani 1 1 d . . . . .
H18 H 0.3358 0.4336 -0.0589 0.125 Uiso 1 1 calc R U . . .
C19 C 0.2995(6) 0.4320(2) -0.2915(14) 0.125(3) Uani 1 1 d . . . . .
H19 H 0.2886 0.4561 -0.3067 0.150 Uiso 1 1 calc R U . . .
C20 C 0.2876(7) 0.4116(3) -0.4114(14) 0.147(3) Uani 1 1 d . . . . .
H20 H 0.2698 0.4224 -0.5073 0.176 Uiso 1 1 calc R U . . .
C21 C 0.2986(7) 0.3782(3) -0.4071(9) 0.134(2) Uani 1 1 d . . . . .
H21 H 0.2875 0.3652 -0.4969 0.160 Uiso 1 1 calc R U . . .
C22 C 0.3285(5) 0.36127(14) -0.2603(9) 0.1011(19) Uani 1 1 d . . . . .
C23 C 0.3424(6) 0.32516(17) -0.2147(9) 0.1087(18) Uani 1 1 d . . . . .
H23 H 0.3359 0.3054 -0.2767 0.130 Uiso 1 1 calc R U . . .
C24 C 0.3661(5) 0.32668(13) -0.0670(8) 0.0931(16) Uani 1 1 d . . . . .
C25 C 0.3807(7) 0.3718(2) 0.1456(10) 0.151(3) Uani 1 1 d . . . . .
H25A H 0.2950 0.3743 0.1622 0.226 Uiso 1 1 calc R U . . .
H25B H 0.4235 0.3943 0.1569 0.226 Uiso 1 1 calc R U . . .
H25C H 0.4319 0.3557 0.2194 0.226 Uiso 1 1 calc R U . . .
C26 C 0.5086(9) 0.2751(2) 0.0507(13) 0.170(3) Uani 1 1 d D . . . .
H26A H 0.4899 0.2513 0.0760 0.204 Uiso 1 1 calc R U . . .
H26B H 0.5230 0.2747 -0.0510 0.204 Uiso 1 1 calc R U . . .
C27 C 0.6307(9) 0.2865(4) 0.160(3) 0.289(13) Uani 1 1 d D . . . .
C28 C 0.2956(8) 0.2845(2) 0.1080(11) 0.145(3) Uani 1 1 d . . . . .
C29 C 0.0838(6) 0.29620(14) 0.1468(7) 0.0935(16) Uani 1 1 d . . . . .
C30 C 0.1071(11) 0.3051(3) 0.3131(8) 0.172(4) Uani 1 1 d . . . . .
H30A H 0.1718 0.2895 0.3735 0.258 Uiso 1 1 calc R U . . .
H30B H 0.0265 0.3027 0.3424 0.258 Uiso 1 1 calc R U . . .
H30C H 0.1379 0.3288 0.3301 0.258 Uiso 1 1 calc R U . . .
C31 C -0.0182(9) 0.3221(3) 0.0619(12) 0.170(4) Uani 1 1 d . . . . .
H31A H 0.0128 0.3456 0.0879 0.255 Uiso 1 1 calc R U . . .
H31B H -0.0986 0.3186 0.0906 0.255 Uiso 1 1 calc R U . . .
H31C H -0.0337 0.3186 -0.0468 0.255 Uiso 1 1 calc R U . . .
C32 C 0.0360(11) 0.2596(2) 0.1135(16) 0.209(6) Uani 1 1 d . . . . .
H32A H 0.0040 0.2565 0.0045 0.313 Uiso 1 1 calc R U . . .
H32B H -0.0337 0.2552 0.1612 0.313 Uiso 1 1 calc R U . . .
H32C H 0.1069 0.2436 0.1535 0.313 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 1.337(6) . ?
F2 C11 1.319(6) . ?
F3 C11 1.317(5) . ?
O1 C12 1.204(5) . ?
O2 C12 1.312(5) . ?
O2 C13 1.472(5) . ?
N1 C1 1.378(5) . ?
N1 C8 1.390(5) . ?
N1 C9 1.446(5) . ?
N2 C12 1.391(5) . ?
N2 C8 1.401(5) . ?
N2 C10 1.459(5) . ?
C1 C2 1.385(6) . ?
C1 C6 1.414(6) . ?
C2 C3 1.357(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(6) . ?
C7 C8 1.350(6) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.484(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 C14 1.491(8) . ?
C13 C16 1.498(8) . ?
C13 C15 1.507(9) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
F4 C27 1.172(11) . ?
F5 C27 1.278(15) . ?
F6 C27 1.30(2) . ?
O3 C28 1.230(8) . ?
O4 C28 1.282(9) . ?
O4 C29 1.452(6) . ?
N3 C24 1.366(7) . ?
N3 C25 1.389(9) . ?
N3 C17 1.418(7) . ?
N4 C28 1.360(9) . ?
N4 C24 1.485(8) . ?
N4 C26 1.498(10) . ?
C17 C22 1.390(8) . ?
C17 C18 1.427(8) . ?
C18 C19 1.378(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.312(12) . ?
C19 H19 0.9300 . ?
C20 C21 1.281(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.431(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.433(8) . ?
C23 C24 1.292(8) . ?
C23 H23 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.466(15) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C29 C32 1.485(9) . ?
C29 C30 1.494(9) . ?
C29 C31 1.512(11) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C13 122.2(3) . . ?
C1 N1 C8 107.5(3) . . ?
C1 N1 C9 125.4(3) . . ?
C8 N1 C9 126.8(4) . . ?
C12 N2 C8 120.3(3) . . ?
C12 N2 C10 117.9(3) . . ?
C8 N2 C10 119.2(3) . . ?
N1 C1 C2 129.7(4) . . ?
N1 C1 C6 108.1(3) . . ?
C2 C1 C6 122.1(4) . . ?
C3 C2 C1 117.6(5) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.8(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.4(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 135.6(5) . . ?
C5 C6 C1 118.1(4) . . ?
C7 C6 C1 106.4(4) . . ?
C8 C7 C6 108.2(4) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 N1 109.7(4) . . ?
C7 C8 N2 129.9(4) . . ?
N1 C8 N2 120.4(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 112.4(4) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
F3 C11 F2 106.5(4) . . ?
F3 C11 F1 105.4(4) . . ?
F2 C11 F1 107.0(4) . . ?
F3 C11 C10 113.5(4) . . ?
F2 C11 C10 111.3(4) . . ?
F1 C11 C10 112.7(4) . . ?
O1 C12 O2 127.7(4) . . ?
O1 C12 N2 122.8(4) . . ?
O2 C12 N2 109.4(4) . . ?
O2 C13 C14 109.4(4) . . ?
O2 C13 C16 102.7(4) . . ?
C14 C13 C16 111.1(5) . . ?
O2 C13 C15 110.3(5) . . ?
C14 C13 C15 111.5(5) . . ?
C16 C13 C15 111.5(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C28 O4 C29 122.1(5) . . ?
C24 N3 C25 135.6(7) . . ?
C24 N3 C17 103.1(5) . . ?
C25 N3 C17 121.2(6) . . ?
C28 N4 C24 123.0(6) . . ?
C28 N4 C26 118.9(6) . . ?
C24 N4 C26 116.0(6) . . ?
C22 C17 N3 107.3(5) . . ?
C22 C17 C18 120.4(6) . . ?
N3 C17 C18 132.3(6) . . ?
C19 C18 C17 115.4(6) . . ?
C19 C18 H18 122.3 . . ?
C17 C18 H18 122.3 . . ?
C20 C19 C18 122.4(7) . . ?
C20 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C21 C20 C19 125.3(9) . . ?
C21 C20 H20 117.4 . . ?
C19 C20 H20 117.4 . . ?
C20 C21 C22 118.2(8) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C17 C22 C21 118.4(6) . . ?
C17 C22 C23 108.8(6) . . ?
C21 C22 C23 132.7(7) . . ?
C24 C23 C22 103.3(6) . . ?
C24 C23 H23 128.3 . . ?
C22 C23 H23 128.3 . . ?
C23 C24 N3 117.5(6) . . ?
C23 C24 N4 128.1(6) . . ?
N3 C24 N4 114.4(6) . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N4 116.1(9) . . ?
C27 C26 H26A 108.3 . . ?
N4 C26 H26A 108.3 . . ?
C27 C26 H26B 108.3 . . ?
N4 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?
F4 C27 F5 111.8(11) . . ?
F4 C27 F6 105(2) . . ?
F5 C27 F6 94.0(16) . . ?
F4 C27 C26 127.5(15) . . ?
F5 C27 C26 111.6(12) . . ?
F6 C27 C26 100.2(10) . . ?
O3 C28 O4 126.0(8) . . ?
O3 C28 N4 120.5(8) . . ?
O4 C28 N4 113.2(6) . . ?
O4 C29 C32 113.0(5) . . ?
O4 C29 C30 113.5(6) . . ?
C32 C29 C30 111.9(7) . . ?
O4 C29 C31 101.7(5) . . ?
C32 C29 C31 110.6(8) . . ?
C30 C29 C31 105.5(7) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C8 N1 C1 C2 177.6(4) . . . . ?
C9 N1 C1 C2 3.4(7) . . . . ?
C8 N1 C1 C6 -1.7(4) . . . . ?
C9 N1 C1 C6 -176.0(4) . . . . ?
N1 C1 C2 C3 179.0(4) . . . . ?
C6 C1 C2 C3 -1.7(7) . . . . ?
C1 C2 C3 C4 0.4(8) . . . . ?
C2 C3 C4 C5 1.3(10) . . . . ?
C3 C4 C5 C6 -1.7(10) . . . . ?
C4 C5 C6 C7 -180.0(6) . . . . ?
C4 C5 C6 C1 0.4(8) . . . . ?
N1 C1 C6 C5 -179.2(4) . . . . ?
C2 C1 C6 C5 1.4(7) . . . . ?
N1 C1 C6 C7 1.0(5) . . . . ?
C2 C1 C6 C7 -178.4(4) . . . . ?
C5 C6 C7 C8 -179.6(6) . . . . ?
C1 C6 C7 C8 0.1(5) . . . . ?
C6 C7 C8 N1 -1.2(5) . . . . ?
C6 C7 C8 N2 -179.1(4) . . . . ?
C1 N1 C8 C7 1.8(5) . . . . ?
C9 N1 C8 C7 176.0(4) . . . . ?
C1 N1 C8 N2 180.0(3) . . . . ?
C9 N1 C8 N2 -5.8(6) . . . . ?
C12 N2 C8 C7 -98.3(5) . . . . ?
C10 N2 C8 C7 63.1(6) . . . . ?
C12 N2 C8 N1 83.9(5) . . . . ?
C10 N2 C8 N1 -114.7(4) . . . . ?
C12 N2 C10 C11 -105.7(5) . . . . ?
C8 N2 C10 C11 92.4(5) . . . . ?
N2 C10 C11 F3 -61.6(6) . . . . ?
N2 C10 C11 F2 178.3(4) . . . . ?
N2 C10 C11 F1 58.1(5) . . . . ?
C13 O2 C12 O1 -5.8(8) . . . . ?
C13 O2 C12 N2 176.7(4) . . . . ?
C8 N2 C12 O1 168.6(4) . . . . ?
C10 N2 C12 O1 6.9(7) . . . . ?
C8 N2 C12 O2 -13.8(6) . . . . ?
C10 N2 C12 O2 -175.4(4) . . . . ?
C12 O2 C13 C14 64.7(6) . . . . ?
C12 O2 C13 C16 -177.2(5) . . . . ?
C12 O2 C13 C15 -58.3(6) . . . . ?
C24 N3 C17 C22 -0.6(5) . . . . ?
C25 N3 C17 C22 -176.3(5) . . . . ?
C24 N3 C17 C18 177.5(5) . . . . ?
C25 N3 C17 C18 1.9(8) . . . . ?
C22 C17 C18 C19 -0.6(7) . . . . ?
N3 C17 C18 C19 -178.5(5) . . . . ?
C17 C18 C19 C20 0.1(9) . . . . ?
C18 C19 C20 C21 0.9(12) . . . . ?
C19 C20 C21 C22 -1.2(12) . . . . ?
N3 C17 C22 C21 178.7(4) . . . . ?
C18 C17 C22 C21 0.3(7) . . . . ?
N3 C17 C22 C23 1.3(5) . . . . ?
C18 C17 C22 C23 -177.2(4) . . . . ?
C20 C21 C22 C17 0.6(9) . . . . ?
C20 C21 C22 C23 177.2(7) . . . . ?
C17 C22 C23 C24 -1.4(6) . . . . ?
C21 C22 C23 C24 -178.3(6) . . . . ?
C22 C23 C24 N3 1.0(7) . . . . ?
C22 C23 C24 N4 -180.0(5) . . . . ?
C25 N3 C24 C23 174.4(6) . . . . ?
C17 N3 C24 C23 -0.3(6) . . . . ?
C25 N3 C24 N4 -4.7(9) . . . . ?
C17 N3 C24 N4 -179.4(4) . . . . ?
C28 N4 C24 C23 -100.5(10) . . . . ?
C26 N4 C24 C23 62.7(9) . . . . ?
C28 N4 C24 N3 78.5(9) . . . . ?
C26 N4 C24 N3 -118.3(7) . . . . ?
C28 N4 C26 C27 -106.0(13) . . . . ?
C24 N4 C26 C27 90.0(13) . . . . ?
N4 C26 C27 F4 163.1(19) . . . . ?
N4 C26 C27 F5 -53(2) . . . . ?
N4 C26 C27 F6 45.6(17) . . . . ?
C29 O4 C28 O3 -5.3(13) . . . . ?
C29 O4 C28 N4 -178.6(6) . . . . ?
C24 N4 C28 O3 174.0(8) . . . . ?
C26 N4 C28 O3 11.2(14) . . . . ?
C24 N4 C28 O4 -12.3(12) . . . . ?
C26 N4 C28 O4 -175.2(8) . . . . ?
C28 O4 C29 C32 -49.4(10) . . . . ?
C28 O4 C29 C30 79.3(9) . . . . ?
C28 O4 C29 C31 -168.0(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C32 H32C O3 0.96 2.22 2.856(13) 122.8 .
C23 H23 O3 0.93 2.44 3.284(8) 150.3 4_565
C15 H15C O1 0.96 2.42 3.025(9) 120.5 .
C14 H14A O1 0.96 2.46 3.028(7) 117.5 .
C10 H10B O1 0.97 2.60 3.497(6) 153.8 3_665
C32 H32C O3 0.96 2.22 2.856(13) 122.8 .
C23 H23 O3 0.93 2.44 3.284(8) 150.3 4_565
C15 H15C O1 0.96 2.42 3.025(9) 120.5 .
C14 H14A O1 0.96 2.46 3.028(7) 117.5 .
C10 H10B O1 0.97 2.60 3.497(6) 153.8 3_665
C10 H10B O1 0.97 2.60 3.497(6) 153.8 3_665
C14 H14A O1 0.96 2.46 3.028(7) 117.5 .
C15 H15C O1 0.96 2.42 3.025(9) 120.5 .
C23 H23 O3 0.93 2.44 3.284(8) 150.3 4_565
C32 H32C O3 0.96 2.22 2.856(13) 122.8 .
C10 H10B O1 0.97 2.60 3.497(6) 153.8 3_665
C14 H14A O1 0.96 2.46 3.028(7) 117.5 .
C15 H15C O1 0.96 2.42 3.025(9) 120.5 .
C23 H23 O3 0.93 2.44 3.284(8) 150.3 4_565
C32 H32C O3 0.96 2.22 2.856(13) 122.8 .

_refine_diff_density_max         1.041
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-4



