# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
# 
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data_my-05-133_re_sq
_database_code_depnum_ccdc_archive 'CCDC 2181895'
loop_
_audit_author_name
_audit_author_address
'Dr. Matthias Zeller'
;Purdue University X ray Crystallographer
United States of America
;
_audit_update_record             
;
2022-06-25 deposited with the CCDC.	2023-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H23 F3 N2 O4'
_chemical_formula_weight         364.36

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      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   23.5990(6)
_cell_length_b                   23.5990(6)
_cell_length_c                   10.4104(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5020.9(3)
_cell_formula_units_Z            9
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9772
_cell_measurement_theta_min      3.7461
_cell_measurement_theta_max      72.4903

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.163
_exptl_absorpt_coefficient_mu    0.808
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48825
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.767
_diffrn_reflns_theta_max         72.483
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.915
_reflns_number_total             3995
_reflns_number_gt                3913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_max     0.805
_reflns_Friedel_fraction_full    0.832

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Apex4 v2021.4-0 (Bruker, 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1275(Hübschle et al., 2011)
SQUEEZE/PLATON -- Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
;

_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;The structure contains additional 1153 Ang3 of solvent accessible 
voids. No substantial electron density peaks were found in 
the solvent accessible voids (less than 1.15 electron per cubic Angstrom) 
and the residual electron density peaks are not arranged in an 
interpretable pattern. The structure factors were instead augmented 
via reverse Fourier transform methods using the SQUEEZE routine (P. 
van der Sluis & A.L. Spek (1990). Acta Cryst. A46, 194-201) as 
implemented in the program Platon. The resultant FAB file containing the 
structure factor contribution from the electron content of the void 
space was used in together with the original hkl file in the further 
refinement. (The FAB file with details of the Squeeze results is 
appended to this cif file). The Squeeze procedure corrected for 208 
electrons within the solvent accessible voids.,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.6317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1676 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3995
_refine_ls_number_parameters     272
_refine_ls_number_restraints     160
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
C16 C 0.4058(3) 0.5893(3) 0.7709(5) 0.0689(13) Uani 0.791(10) 1 d D U P A 1
F1 F 0.3475(2) 0.5560(3) 0.7190(6) 0.0929(15) Uani 0.791(10) 1 d D U P A 1
F2 F 0.4020(2) 0.5737(3) 0.8931(3) 0.1187(15) Uani 0.791(10) 1 d D U P A 1
F3 F 0.42309(16) 0.65113(12) 0.7665(7) 0.1093(17) Uani 0.791(10) 1 d D U P A 1
C16A C 0.4094(12) 0.5955(10) 0.744(2) 0.084(5) Uani 0.209(10) 1 d D U P A 2
F1A F 0.4245(6) 0.6181(10) 0.8644(16) 0.114(5) Uani 0.209(10) 1 d D U P A 2
F2A F 0.4067(8) 0.6433(7) 0.682(2) 0.116(4) Uani 0.209(10) 1 d D U P A 2
F3A F 0.3486(8) 0.5462(8) 0.7526(19) 0.095(6) Uani 0.209(10) 1 d D U P A 2
O1 O 0.47174(6) 0.38276(5) 0.27759(11) 0.0416(3) Uani 1 1 d . . . . .
O2 O 0.42999(7) 0.39145(5) 0.09054(11) 0.0417(3) Uani 1 1 d . . . . .
H5 H 0.418207 0.351590 0.083754 0.058(7) Uiso 1 1 calc R . . . .
O3 O 0.39928(5) 0.45183(7) 0.40935(12) 0.0483(3) Uani 1 1 d . . . . .
O4 O 0.51505(7) 0.61713(7) 0.71965(15) 0.0603(4) Uani 1 1 d . . . . .
N1 N 0.50291(5) 0.50777(6) 0.34661(11) 0.0256(2) Uani 1 1 d . . . . .
N2 N 0.43320(7) 0.52159(7) 0.63636(13) 0.0415(3) Uani 1 1 d . . . . .
H4 H 0.390617 0.496224 0.627796 0.052(6) Uiso 1 1 calc R . . . .
C1 C 0.48165(7) 0.48621(7) 0.21497(13) 0.0258(3) Uani 1 1 d . . . . .
H1 H 0.444088 0.492804 0.193052 0.031 Uiso 1 1 calc R U . . .
C2 C 0.53993(7) 0.53012(7) 0.13211(13) 0.0260(3) Uani 1 1 d . . . . .
H2 H 0.548793 0.511412 0.053543 0.031 Uiso 1 1 calc R U . . .
C3 C 0.59621(7) 0.57267(7) 0.22074(13) 0.0266(3) Uani 1 1 d . . . . .
H3 H 0.640830 0.581234 0.196552 0.032 Uiso 1 1 calc R U . . .
C4 C 0.57415(7) 0.55302(7) 0.35759(14) 0.0290(3) Uani 1 1 d . . . . .
H4A H 0.596162 0.530842 0.396529 0.035 Uiso 1 1 calc R U . . .
H4AB H 0.583506 0.591642 0.410377 0.035 Uiso 1 1 calc R U . . .
C5 C 0.56536(7) 0.60300(7) 0.13808(13) 0.0280(3) Uani 1 1 d . . . . .
C6 C 0.60497(8) 0.64149(8) 0.02227(16) 0.0371(3) Uani 1 1 d . . . . .
H6A H 0.575578 0.642685 -0.042796 0.056 Uiso 1 1 calc R U . . .
H6B H 0.628164 0.620392 -0.013752 0.056 Uiso 1 1 calc R U . . .
H6C H 0.636749 0.686228 0.048567 0.056 Uiso 1 1 calc R U . . .
C7 C 0.52451(8) 0.62967(8) 0.19549(18) 0.0376(3) Uani 1 1 d . . . . .
H7A H 0.552954 0.675690 0.218906 0.056 Uiso 1 1 calc R U . . .
H7B H 0.502028 0.604422 0.272332 0.056 Uiso 1 1 calc R U . . .
H7C H 0.492089 0.626177 0.132402 0.056 Uiso 1 1 calc R U . . .
C8 C 0.46104(7) 0.41409(7) 0.19977(13) 0.0286(3) Uani 1 1 d . . . . .
C9 C 0.45748(7) 0.48582(7) 0.43824(14) 0.0315(3) Uani 1 1 d . . . . .
C10 C 0.47781(8) 0.50276(8) 0.57827(15) 0.0355(3) Uani 1 1 d . . . . .
H10 H 0.522865 0.541805 0.579911 0.043 Uiso 1 1 calc R U . . .
C11 C 0.47961(9) 0.44632(9) 0.65254(15) 0.0424(4) Uani 1 1 d . . . . .
C12 C 0.41413(11) 0.38224(10) 0.6454(2) 0.0560(5) Uani 1 1 d . . . . .
H12A H 0.406476 0.365654 0.557135 0.084 Uiso 1 1 calc R U . . .
H12B H 0.378798 0.390143 0.671721 0.084 Uiso 1 1 calc R U . . .
H12C H 0.415210 0.349914 0.702941 0.084 Uiso 1 1 calc R U . . .
C13 C 0.49555(11) 0.46711(12) 0.79357(18) 0.0564(5) Uani 1 1 d . . . . .
H13A H 0.535175 0.510215 0.798214 0.085 Uiso 1 1 calc R U . . .
H13B H 0.502722 0.435072 0.839864 0.085 Uiso 1 1 calc R U . . .
H13C H 0.458937 0.469312 0.832720 0.085 Uiso 1 1 calc R U . . .
C14 C 0.53401(10) 0.43651(10) 0.59636(18) 0.0483(4) Uani 1 1 d . . . . .
H14A H 0.524263 0.423302 0.506149 0.072 Uiso 1 1 calc R U . . .
H14B H 0.536769 0.402374 0.644828 0.072 Uiso 1 1 calc R U . . .
H14C H 0.575829 0.477578 0.602125 0.072 Uiso 1 1 calc R U . . .
C15 C 0.45740(10) 0.57757(10) 0.70259(19) 0.0504(5) Uani 1 1 d . 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
C16 F3 1.305(6) . ?
C16 F1 1.313(6) . ?
C16 F2 1.316(6) . ?
C16 C15 1.549(7) . ?
C16A F3A 1.323(19) . ?
C16A F2A 1.33(2) . ?
C16A F1A 1.342(19) . ?
C16A C15 1.46(3) . ?
O1 C8 1.2056(19) . ?
O2 C8 1.3130(18) . ?
O2 H5 0.8400 . ?
O3 C9 1.2324(19) . ?
O4 C15 1.218(2) . ?
N1 C9 1.3311(18) . ?
N1 C1 1.4606(18) . ?
N1 C4 1.4781(17) . ?
N2 C15 1.339(2) . ?
N2 C10 1.463(2) . ?
N2 H4 0.8800 . ?
C1 C2 1.5113(19) . ?
C1 C8 1.5266(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.5133(19) . ?
C2 C5 1.5134(19) . ?
C2 H2 1.0000 . ?
C3 C4 1.508(2) . ?
C3 C5 1.518(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C7 1.513(2) . ?
C5 C6 1.518(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.524(2) . ?
C10 C11 1.559(3) . ?
C10 H10 1.0000 . ?
C11 C14 1.530(3) . ?
C11 C12 1.531(3) . ?
C11 C13 1.534(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
F3 C16 F1 107.6(6) . . ?
F3 C16 F2 106.6(4) . . ?
F1 C16 F2 108.9(4) . . ?
F3 C16 C15 110.5(4) . . ?
F1 C16 C15 112.8(5) . . ?
F2 C16 C15 110.1(5) . . ?
F3A C16A F2A 107(2) . . ?
F3A C16A F1A 103.9(18) . . ?
F2A C16A F1A 103.6(19) . . ?
F3A C16A C15 115(2) . . ?
F2A C16A C15 118.5(17) . . ?
F1A C16A C15 107.4(17) . . ?
C8 O2 H5 109.5 . . ?
C9 N1 C1 117.86(11) . . ?
C9 N1 C4 129.01(12) . . ?
C1 N1 C4 113.12(11) . . ?
C15 N2 C10 119.73(15) . . ?
C15 N2 H4 120.1 . . ?
C10 N2 H4 120.1 . . ?
N1 C1 C2 105.09(10) . . ?
N1 C1 C8 110.37(11) . . ?
C2 C1 C8 112.25(12) . . ?
N1 C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C8 C1 H1 109.7 . . ?
C1 C2 C3 107.63(11) . . ?
C1 C2 C5 117.62(12) . . ?
C3 C2 C5 60.20(9) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C5 C2 H2 118.9 . . ?
C4 C3 C2 108.57(11) . . ?
C4 C3 C5 120.48(12) . . ?
C2 C3 C5 59.90(9) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
C5 C3 H3 117.8 . . ?
N1 C4 C3 104.02(11) . . ?
N1 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
N1 C4 H4AB 111.0 . . ?
C3 C4 H4AB 111.0 . . ?
H4A C4 H4AB 109.0 . . ?
C7 C5 C2 121.05(12) . . ?
C7 C5 C6 113.25(13) . . ?
C2 C5 C6 115.03(12) . . ?
C7 C5 C3 121.86(13) . . ?
C2 C5 C3 59.90(9) . . ?
C6 C5 C3 115.81(12) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 O2 125.31(14) . . ?
O1 C8 C1 124.49(13) . . ?
O2 C8 C1 110.20(12) . . ?
O3 C9 N1 119.80(13) . . ?
O3 C9 C10 120.42(13) . . ?
N1 C9 C10 119.78(12) . . ?
N2 C10 C9 107.16(14) . . ?
N2 C10 C11 112.69(13) . . ?
C9 C10 C11 112.94(13) . . ?
N2 C10 H10 108.0 . . ?
C9 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C14 C11 C12 109.94(17) . . ?
C14 C11 C13 108.91(17) . . ?
C12 C11 C13 109.09(15) . . ?
C14 C11 C10 108.85(14) . . ?
C12 C11 C10 112.01(16) . . ?
C13 C11 C10 107.97(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 N2 126.39(19) . . ?
O4 C15 C16A 117.9(8) . . ?
N2 C15 C16A 115.3(8) . . ?
O4 C15 C16 118.2(2) . . ?
N2 C15 C16 115.3(2) . . ?

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
C9 N1 C1 C2 167.63(13) . . . . ?
C4 N1 C1 C2 -11.57(15) . . . . ?
C9 N1 C1 C8 -71.14(16) . . . . ?
C4 N1 C1 C8 109.67(13) . . . . ?
N1 C1 C2 C3 4.98(14) . . . . ?
C8 C1 C2 C3 -115.02(13) . . . . ?
N1 C1 C2 C5 -60.05(15) . . . . ?
C8 C1 C2 C5 179.96(12) . . . . ?
C1 C2 C3 C4 2.83(15) . . . . ?
C5 C2 C3 C4 115.07(13) . . . . ?
C1 C2 C3 C5 -112.25(13) . . . . ?
C9 N1 C4 C3 -165.90(14) . . . . ?
C1 N1 C4 C3 13.19(15) . . . . ?
C2 C3 C4 N1 -9.31(15) . . . . ?
C5 C3 C4 N1 56.09(16) . . . . ?
C1 C2 C5 C7 -15.9(2) . . . . ?
C3 C2 C5 C7 -111.30(15) . . . . ?
C1 C2 C5 C6 -158.04(13) . . . . ?
C3 C2 C5 C6 106.55(14) . . . . ?
C1 C2 C5 C3 95.41(13) . . . . ?
C4 C3 C5 C7 15.1(2) . . . . ?
C2 C3 C5 C7 109.98(15) . . . . ?
C4 C3 C5 C2 -94.93(13) . . . . ?
C4 C3 C5 C6 159.84(13) . . . . ?
C2 C3 C5 C6 -105.24(14) . . . . ?
N1 C1 C8 O1 -12.3(2) . . . . ?
C2 C1 C8 O1 104.55(17) . . . . ?
N1 C1 C8 O2 167.44(12) . . . . ?
C2 C1 C8 O2 -75.68(15) . . . . ?
C1 N1 C9 O3 -4.5(2) . . . . ?
C4 N1 C9 O3 174.58(15) . . . . ?
C1 N1 C9 C10 175.39(14) . . . . ?
C4 N1 C9 C10 -5.6(2) . . . . ?
C15 N2 C10 C9 -129.53(18) . . . . ?
C15 N2 C10 C11 105.63(19) . . . . ?
O3 C9 C10 N2 -44.5(2) . . . . ?
N1 C9 C10 N2 135.69(14) . . . . ?
O3 C9 C10 C11 80.2(2) . . . . ?
N1 C9 C10 C11 -99.63(17) . . . . ?
N2 C10 C11 C14 -172.30(14) . . . . ?
C9 C10 C11 C14 66.09(17) . . . . ?
N2 C10 C11 C12 65.92(18) . . . . ?
C9 C10 C11 C12 -55.70(19) . . . . ?
N2 C10 C11 C13 -54.21(18) . . . . ?
C9 C10 C11 C13 -175.83(15) . . . . ?
C10 N2 C15 O4 1.1(3) . . . . ?
C10 N2 C15 C16A 173.2(9) . . . . ?
C10 N2 C15 C16 -174.3(3) . . . . ?
F3A C16A C15 O4 -164.1(14) . . . . ?
F2A C16A C15 O4 67.8(17) . . . . ?
F1A C16A C15 O4 -48.9(16) . . . . ?
F3A C16A C15 N2 23(2) . . . . ?
F2A C16A C15 N2 -105.0(16) . . . . ?
F1A C16A C15 N2 138.3(13) . . . . ?
F3 C16 C15 O4 41.1(6) . . . . ?
F1 C16 C15 O4 161.6(5) . . . . ?
F2 C16 C15 O4 -76.4(4) . . . . ?
F3 C16 C15 N2 -143.0(4) . . . . ?
F1 C16 C15 N2 -22.5(6) . . . . ?
F2 C16 C15 N2 99.4(4) . . . . ?

_refine_diff_density_max         0.102
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.023



