#------------------------------------------------------------------------------
#$Date: 2024-04-06 02:42:34 +0300 (Sat, 06 Apr 2024) $
#$Revision: 291117 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023026.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023026
loop_
_publ_author_name
'Yıldırım, Sema Öztürk'
'Akkurt, Mehmet'
'Pehlivanlar, Ezgi'
'Çetin, Gökalp'
'Şimşek, Rahime'
'Butcher, Ray J.'
'Bhattarai, Ajaya'
_publ_section_title
;
 Syntheses, characterizations, crystal structures and Hirshfeld surface
 analyses of methyl
 4-[4-(di-fluorometh-oxy)phen-yl]-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate,
 isopropyl
 4-[4-(di-fluoro-meth-oxy)phen-yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate
 and tert-butyl
 4-[4-(di-fluoro-meth-oxy)phen-yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.
;
_journal_coeditor_code           JY2044
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              281
_journal_page_last               288
_journal_paper_doi               10.1107/S2056989024001233
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C23 H27 F2 N O4'
_chemical_formula_moiety         'C23 H27 F2 N O4'
_chemical_formula_sum            'C23 H27 F2 N O4'
_chemical_formula_weight         419.45
_chemical_name_systematic
'Isopropyl 4-[4-(difluoromethoxy)phenyl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.255(3)
_cell_length_b                   15.694(3)
_cell_length_c                   21.903(4)
_cell_measurement_reflns_used    9744
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.97
_cell_measurement_theta_min      2.30
_cell_volume                     4212.6(15)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX2 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Quest with Photon 2 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            102650
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.084
_diffrn_reflns_theta_min         2.305
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         8537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0504
_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)+(0.0602P)²+1.7687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                6743
_reflns_number_total             8537
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2044sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2023025--2023027.cif.'
_cod_original_cell_volume        4212.3(14)
_cod_database_code               2023026
_cod_database_fobs_code          2023026
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.58006(8) 0.07640(5) 0.03801(3) 0.0364(2) Uani d 1 . .
F F2 0.64472(7) 0.00608(5) 0.11460(4) 0.0349(2) Uani d 1 . .
O O1 0.34068(6) 0.45116(5) 0.16296(3) 0.01817(15) Uani d 1 . .
O O2 0.29601(6) 0.27319(5) 0.34751(4) 0.02216(16) Uani d 1 . .
O O3 0.41830(6) 0.29307(5) 0.42284(3) 0.01679(14) Uani d 1 . .
O O4 0.46707(7) 0.03988(5) 0.11352(4) 0.02388(17) Uani d 1 . .
N N1 0.63612(7) 0.39398(5) 0.29383(4) 0.01310(14) Uani d 1 . .
C C1 0.59145(7) 0.43524(5) 0.24486(4) 0.01197(15) Uani d 1 . .
C C2 0.66452(8) 0.49617(6) 0.21159(5) 0.01519(17) Uani d 1 . .
H H2A 0.708624 0.464675 0.181174 0.018 Uiso calc 1 . .
H H2B 0.715096 0.523476 0.240904 0.018 Uiso calc 1 . .
C C3 0.59723(8) 0.56435(6) 0.17941(5) 0.01630(17) Uani d 1 . .
H H3A 0.645890 0.598521 0.152912 0.020 Uiso calc 1 . .
H H3B 0.565594 0.603050 0.210406 0.020 Uiso calc 1 . .
C C4 0.50494(8) 0.52715(6) 0.14056(4) 0.01366(16) Uani d 1 . .
C C5 0.43666(8) 0.46417(6) 0.17775(4) 0.01252(16) Uani d 1 . .
C C6 0.48713(7) 0.41800(5) 0.22754(4) 0.01160(15) Uani d 1 . .
C C7 0.42689(7) 0.34420(5) 0.25648(4) 0.01133(15) Uani d 1 . .
H H7A 0.347627 0.359096 0.258478 0.014 Uiso calc 1 . .
C C8 0.46808(7) 0.33050(6) 0.32152(4) 0.01173(15) Uani d 1 . .
C C9 0.57283(7) 0.35044(6) 0.33615(4) 0.01219(15) Uani d 1 . .
C C10 0.43280(9) 0.59982(7) 0.11768(6) 0.0233(2) Uani d 1 . .
H H10A 0.402326 0.630702 0.152635 0.035 Uiso calc 1 . .
H H10B 0.373259 0.576488 0.092926 0.035 Uiso calc 1 . .
H H10C 0.476524 0.638908 0.092797 0.035 Uiso calc 1 . .
C C11 0.55042(10) 0.47676(8) 0.08592(5) 0.0232(2) Uani d 1 . .
H H11A 0.599642 0.513276 0.062280 0.035 Uiso calc 1 . .
H H11B 0.489998 0.457985 0.059883 0.035 Uiso calc 1 . .
H H11C 0.590601 0.426920 0.100808 0.035 Uiso calc 1 . .
C C12 0.63489(8) 0.33279(7) 0.39391(4) 0.01612(17) Uani d 1 . .
H H12A 0.595564 0.290247 0.418173 0.024 Uiso calc 1 . .
H H12B 0.641987 0.385556 0.417509 0.024 Uiso calc 1 . .
H H12C 0.707624 0.311051 0.383743 0.024 Uiso calc 1 . .
C C13 0.38614(8) 0.29573(6) 0.36382(4) 0.01362(16) Uani d 1 . .
C C14 0.34202(9) 0.25787(7) 0.46746(5) 0.0208(2) Uani d 1 . .
H H14A 0.299229 0.210294 0.448771 0.025 Uiso calc 1 . .
C C15 0.26612(14) 0.32793(11) 0.48827(7) 0.0461(4) Uani d 1 . .
H H15A 0.226327 0.350637 0.453038 0.069 Uiso calc 1 . .
H H15B 0.308701 0.373654 0.507282 0.069 Uiso calc 1 . .
H H15C 0.214105 0.304965 0.518006 0.069 Uiso calc 1 . .
C C16 0.41149(11) 0.22458(8) 0.51914(5) 0.0268(2) Uani d 1 . .
H H16A 0.462584 0.181853 0.503408 0.040 Uiso calc 1 . .
H H16B 0.364532 0.198499 0.550169 0.040 Uiso calc 1 . .
H H16C 0.452451 0.271766 0.537407 0.040 Uiso calc 1 . .
C C17 0.43931(7) 0.26381(6) 0.21739(4) 0.01218(15) Uani d 1 . .
C C18 0.54172(8) 0.23882(6) 0.19612(5) 0.01650(17) Uani d 1 . .
H H18A 0.603453 0.272969 0.205585 0.020 Uiso calc 1 . .
C C19 0.55622(8) 0.16531(7) 0.16141(5) 0.01900(19) Uani d 1 . .
H H19A 0.626783 0.148978 0.147783 0.023 Uiso calc 1 . .
C C20 0.46524(8) 0.11639(6) 0.14715(4) 0.01634(17) Uani d 1 . .
C C21 0.36233(8) 0.14000(6) 0.16660(4) 0.01612(17) Uani d 1 . .
H H21A 0.300604 0.106507 0.155987 0.019 Uiso calc 1 . .
C C22 0.34957(8) 0.21340(6) 0.20194(4) 0.01432(16) Uani d 1 . .
H H22A 0.278885 0.229241 0.215665 0.017 Uiso calc 1 . .
C C23 0.55424(9) 0.01649(7) 0.08023(5) 0.01990(19) Uani d 1 . .
H H23A 0.537493 -0.038295 0.058878 0.024 Uiso calc 1 . .
H H1N 0.7011(13) 0.4077(9) 0.3055(7) 0.020(3) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 O3 C14 . . 117.69(8) ?
C23 O4 C20 . . 121.93(9) ?
C1 N1 C9 . . 122.21(8) ?
C1 N1 H1N . . 118.8(10) ?
C9 N1 H1N . . 116.2(10) ?
C6 C1 N1 . . 120.05(8) ?
C6 C1 C2 . . 123.54(8) ?
N1 C1 C2 . . 116.37(8) ?
C1 C2 C3 . . 110.46(8) ?
C1 C2 H2A . . 109.6 ?
C3 C2 H2A . . 109.6 ?
C1 C2 H2B . . 109.6 ?
C3 C2 H2B . . 109.6 ?
H2A C2 H2B . . 108.1 ?
C2 C3 C4 . . 112.90(8) ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3B . . 109.0 ?
C4 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
C10 C4 C5 . . 109.91(8) ?
C10 C4 C3 . . 108.98(8) ?
C5 C4 C3 . . 110.77(8) ?
C10 C4 C11 . . 109.76(9) ?
C5 C4 C11 . . 106.27(8) ?
C3 C4 C11 . . 111.13(8) ?
O1 C5 C6 . . 121.38(8) ?
O1 C5 C4 . . 119.16(8) ?
C6 C5 C4 . . 119.38(8) ?
C1 C6 C5 . . 120.78(8) ?
C1 C6 C7 . . 119.60(8) ?
C5 C6 C7 . . 119.36(8) ?
C6 C7 C8 . . 109.72(7) ?
C6 C7 C17 . . 110.35(7) ?
C8 C7 C17 . . 111.88(7) ?
C6 C7 H7A . . 108.3 ?
C8 C7 H7A . . 108.3 ?
C17 C7 H7A . . 108.3 ?
C9 C8 C13 . . 125.54(8) ?
C9 C8 C7 . . 119.98(8) ?
C13 C8 C7 . . 114.47(8) ?
C8 C9 N1 . . 118.91(8) ?
C8 C9 C12 . . 129.36(8) ?
N1 C9 C12 . . 111.73(8) ?
C4 C10 H10A . . 109.5 ?
C4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C4 C11 H11A . . 109.5 ?
C4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O2 C13 O3 . . 122.53(9) ?
O2 C13 C8 . . 122.95(9) ?
O3 C13 C8 . . 114.49(8) ?
O3 C14 C16 . . 105.76(9) ?
O3 C14 C15 . . 108.70(9) ?
C16 C14 C15 . . 111.89(11) ?
O3 C14 H14A . . 110.1 ?
C16 C14 H14A . . 110.1 ?
C15 C14 H14A . . 110.1 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 C22 . . 117.93(9) ?
C18 C17 C7 . . 120.50(8) ?
C22 C17 C7 . . 121.58(8) ?
C19 C18 C17 . . 121.99(9) ?
C19 C18 H18A . . 119.0 ?
C17 C18 H18A . . 119.0 ?
C20 C19 C18 . . 118.55(9) ?
C20 C19 H19A . . 120.7 ?
C18 C19 H19A . . 120.7 ?
C21 C20 C19 . . 121.00(9) ?
C21 C20 O4 . . 113.85(9) ?
C19 C20 O4 . . 125.15(9) ?
C20 C21 C22 . . 119.62(9) ?
C20 C21 H21A . . 120.2 ?
C22 C21 H21A . . 120.2 ?
C17 C22 C21 . . 120.89(9) ?
C17 C22 H22A . . 119.6 ?
C21 C22 H22A . . 119.6 ?
O4 C23 F2 . . 112.53(9) ?
O4 C23 F1 . . 111.46(9) ?
F2 C23 F1 . . 105.81(10) ?
O4 C23 H23A . . 109.0 ?
F2 C23 H23A . . 109.0 ?
F1 C23 H23A . . 109.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C23 . 1.3561(13) ?
F2 C23 . 1.3501(13) ?
O1 C5 . 1.2369(12) ?
O2 C13 . 1.2136(12) ?
O3 C13 . 1.3521(12) ?
O3 C14 . 1.4608(12) ?
O4 C23 . 1.3445(14) ?
O4 C20 . 1.4089(12) ?
N1 C1 . 1.3673(12) ?
N1 C9 . 1.3884(12) ?
N1 H1N . 0.863(16) ?
C1 C6 . 1.3606(13) ?
C1 C2 . 1.4991(13) ?
C2 C3 . 1.5236(14) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.5311(14) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C10 . 1.5276(14) ?
C4 C5 . 1.5297(13) ?
C4 C11 . 1.5390(15) ?
C5 C6 . 1.4481(13) ?
C6 C7 . 1.5127(12) ?
C7 C8 . 1.5265(13) ?
C7 C17 . 1.5323(13) ?
C7 H7A . 1.0000 ?
C8 C9 . 1.3595(13) ?
C8 C13 . 1.4712(13) ?
C9 C12 . 1.5019(13) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C14 C16 . 1.5098(16) ?
C14 C15 . 1.5106(18) ?
C14 H14A . 1.0000 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 C18 . 1.3950(13) ?
C17 C22 . 1.3963(13) ?
C18 C19 . 1.3930(14) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.3892(14) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.3817(14) ?
C21 C22 . 1.3966(14) ?
C21 H21A . 0.9500 ?
C22 H22A . 0.9500 ?
C23 H23A . 1.0000 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 6_656 0.863(16) 1.967(16) 2.8258(12) 173.0(14) yes
C2 H2A F2 8_765 0.99 2.40 3.1626(13) 132.9 yes
C12 H12A O3 . 0.98 2.18 2.7991(14) 120.2 yes
C19 H19A F2 . 0.95 2.37 2.9106(14) 115.9 yes
C23 H23A F1 5_655 1.00 2.63 3.3972(14) 133.2 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C6 . . . . -16.13(13) ?
C9 N1 C1 C2 . . . . 165.96(8) ?
C6 C1 C2 C3 . . . . 27.78(13) ?
N1 C1 C2 C3 . . . . -154.38(8) ?
C1 C2 C3 C4 . . . . -50.39(11) ?
C2 C3 C4 C10 . . . . 172.05(8) ?
C2 C3 C4 C5 . . . . 51.01(11) ?
C2 C3 C4 C11 . . . . -66.87(11) ?
C10 C4 C5 O1 . . . . 34.21(12) ?
C3 C4 C5 O1 . . . . 154.69(9) ?
C11 C4 C5 O1 . . . . -84.49(11) ?
C10 C4 C5 C6 . . . . -148.80(9) ?
C3 C4 C5 C6 . . . . -28.32(12) ?
C11 C4 C5 C6 . . . . 92.50(10) ?
N1 C1 C6 C5 . . . . 176.85(8) ?
C2 C1 C6 C5 . . . . -5.39(14) ?
N1 C1 C6 C7 . . . . -9.05(13) ?
C2 C1 C6 C7 . . . . 168.71(8) ?
O1 C5 C6 C1 . . . . -177.45(9) ?
C4 C5 C6 C1 . . . . 5.63(13) ?
O1 C5 C6 C7 . . . . 8.44(13) ?
C4 C5 C6 C7 . . . . -168.48(8) ?
C1 C6 C7 C8 . . . . 29.90(11) ?
C5 C6 C7 C8 . . . . -155.92(8) ?
C1 C6 C7 C17 . . . . -93.83(10) ?
C5 C6 C7 C17 . . . . 80.35(10) ?
C6 C7 C8 C9 . . . . -29.89(11) ?
C17 C7 C8 C9 . . . . 92.94(10) ?
C6 C7 C8 C13 . . . . 149.89(8) ?
C17 C7 C8 C13 . . . . -87.29(9) ?
C13 C8 C9 N1 . . . . -170.87(8) ?
C7 C8 C9 N1 . . . . 8.88(13) ?
C13 C8 C9 C12 . . . . 8.63(16) ?
C7 C8 C9 C12 . . . . -171.62(9) ?
C1 N1 C9 C8 . . . . 16.09(13) ?
C1 N1 C9 C12 . . . . -163.49(8) ?
C14 O3 C13 O2 . . . . 2.82(14) ?
C14 O3 C13 C8 . . . . -178.91(8) ?
C9 C8 C13 O2 . . . . -174.48(10) ?
C7 C8 C13 O2 . . . . 5.75(13) ?
C9 C8 C13 O3 . . . . 7.26(13) ?
C7 C8 C13 O3 . . . . -172.51(8) ?
C13 O3 C14 C16 . . . . 153.97(9) ?
C13 O3 C14 C15 . . . . -85.73(13) ?
C6 C7 C17 C18 . . . . 48.03(11) ?
C8 C7 C17 C18 . . . . -74.44(11) ?
C6 C7 C17 C22 . . . . -132.01(9) ?
C8 C7 C17 C22 . . . . 105.53(10) ?
C22 C17 C18 C19 . . . . -1.13(15) ?
C7 C17 C18 C19 . . . . 178.83(9) ?
C17 C18 C19 C20 . . . . 0.81(16) ?
C18 C19 C20 C21 . . . . 0.29(16) ?
C18 C19 C20 O4 . . . . -178.78(10) ?
C23 O4 C20 C21 . . . . 165.58(10) ?
C23 O4 C20 C19 . . . . -15.29(16) ?
C19 C20 C21 C22 . . . . -1.02(15) ?
O4 C20 C21 C22 . . . . 178.15(9) ?
C18 C17 C22 C21 . . . . 0.38(14) ?
C7 C17 C22 C21 . . . . -179.59(8) ?
C20 C21 C22 C17 . . . . 0.68(15) ?
C20 O4 C23 F2 . . . . 61.18(13) ?
C20 O4 C23 F1 . . . . -57.50(13) ?
