#------------------------------------------------------------------------------
#$Date: 2024-04-06 01:42:34 +0200 (Sat 06 de Apr de 2024) $
#$Revision: 291117 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/30/2023027.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_2023027
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          'C24 H29 F2 N O4'
_chemical_formula_moiety         'C24 H29 F2 N O4'
_chemical_formula_sum            'C24 H29 F2 N O4'
_chemical_formula_weight         433.48
_chemical_name_systematic
;tert-Butyl
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                   12.4094(8)
_cell_length_b                   15.9871(12)
_cell_length_c                   21.9629(15)
_cell_measurement_reflns_used    8996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.27
_cell_volume                     4357.2(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1415
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            56620
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.547
_diffrn_reflns_theta_min         1.854
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6654
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0685P)²+0.6147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1632
_reflns_number_gt                4732
_reflns_number_total             6654
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2044sup1.cif
_cod_data_source_block           III
_cod_depositor_comments
'Adding full bibliography for 2023025--2023027.cif.'
_cod_database_code               2023027
_cod_database_fobs_code          2023027
_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 0.57517(9) 0.94793(6) 0.95792(5) 0.0321(2) Uani d 1 . .
F F2 0.64034(9) 1.01340(7) 0.88027(6) 0.0401(3) Uani d 1 . .
O O1 0.32590(9) 0.56945(7) 0.83355(5) 0.0243(2) Uani d 1 . .
O O2 0.46372(9) 0.98316(7) 0.88197(5) 0.0257(3) Uani d 1 . .
O O3 0.28837(10) 0.73942(9) 0.65077(6) 0.0347(3) Uani d 1 . .
O O4 0.41461(9) 0.72089(6) 0.57815(5) 0.0202(2) Uani d 1 . .
N N1 0.62614(10) 0.63107(7) 0.71106(6) 0.0164(2) Uani d 1 . .
C C1 0.56462(11) 0.67209(8) 0.66740(6) 0.0153(3) Uani d 1 . .
C C2 0.46038(11) 0.69097(8) 0.68021(6) 0.0161(3) Uani d 1 . .
C C3 0.41866(11) 0.67977(8) 0.74513(6) 0.0161(3) Uani d 1 . .
H H3A 0.340091 0.666165 0.743048 0.019 Uiso calc 1 . .
C C4 0.47622(11) 0.60720(8) 0.77510(6) 0.0168(3) Uani d 1 . .
C C5 0.42280(11) 0.55954(8) 0.82239(7) 0.0174(3) Uani d 1 . .
C C6 0.48853(12) 0.49691(8) 0.85970(7) 0.0185(3) Uani d 1 . .
C C7 0.58499(18) 0.46128(13) 0.82234(11) 0.0190(5) Uani d 0.646(3) A 1
H H7A 0.632708 0.429090 0.849834 0.023 Uiso calc 0.646(3) A 1
H H7B 0.557191 0.422424 0.790953 0.023 Uiso calc 0.646(3) A 1
C C8 0.6512(9) 0.5311(7) 0.7910(4) 0.0193(9) Uani d 0.646(3) A 1
H H8A 0.694593 0.560970 0.821974 0.023 Uiso calc 0.646(3) A 1
H H8B 0.701396 0.505677 0.761262 0.023 Uiso calc 0.646(3) A 1
C C11 0.5333(2) 0.54966(15) 0.91386(11) 0.0229(5) Uani d 0.646(3) A 1
H H11A 0.571754 0.598568 0.897985 0.034 Uiso calc 0.646(3) A 1
H H11B 0.582927 0.515342 0.937978 0.034 Uiso calc 0.646(3) A 1
H H11C 0.473433 0.568179 0.939625 0.034 Uiso calc 0.646(3) A 1
C C12 0.4219(2) 0.42518(15) 0.88388(12) 0.0263(6) Uani d 0.646(3) A 1
H H12A 0.361872 0.447214 0.907996 0.039 Uiso calc 0.646(3) A 1
H H12B 0.467089 0.389375 0.909586 0.039 Uiso calc 0.646(3) A 1
H H12C 0.393637 0.392387 0.849735 0.039 Uiso calc 0.646(3) A 1
C C7A 0.6013(3) 0.5198(3) 0.86174(19) 0.0187(8) Uani d 0.354(3) A 2
H H7AA 0.641688 0.476110 0.884062 0.022 Uiso calc 0.354(3) A 2
H H7AB 0.609014 0.572916 0.884527 0.022 Uiso calc 0.354(3) A 2
C C8A 0.6504(16) 0.5304(12) 0.7986(7) 0.0181(13) Uani d 0.354(3) A 2
H H8AA 0.654909 0.475285 0.778147 0.022 Uiso calc 0.354(3) A 2
H H8AB 0.724400 0.553046 0.802297 0.022 Uiso calc 0.354(3) A 2
C C11A 0.4353(4) 0.4888(3) 0.9231(2) 0.0263(10) Uani d 0.354(3) A 2
H H11D 0.449832 0.539399 0.946901 0.039 Uiso calc 0.354(3) A 2
H H11E 0.464945 0.440054 0.944246 0.039 Uiso calc 0.354(3) A 2
H H11F 0.357278 0.481932 0.918181 0.039 Uiso calc 0.354(3) A 2
C C12A 0.4654(4) 0.4132(3) 0.8248(2) 0.0243(9) Uani d 0.354(3) A 2
H H12D 0.387682 0.402116 0.824822 0.036 Uiso calc 0.354(3) A 2
H H12E 0.503045 0.367006 0.845007 0.036 Uiso calc 0.354(3) A 2
H H12F 0.490895 0.418052 0.782704 0.036 Uiso calc 0.354(3) A 2
C C9 0.58058(11) 0.59079(8) 0.75968(6) 0.0167(3) Uani d 1 . .
C C10 0.62756(12) 0.68867(9) 0.61031(7) 0.0207(3) Uani d 1 . .
H H10A 0.595418 0.735945 0.588470 0.031 Uiso calc 1 . .
H H10B 0.626017 0.638871 0.584301 0.031 Uiso calc 1 . .
H H10C 0.702331 0.702011 0.620876 0.031 Uiso calc 1 . .
C C13 0.37937(12) 0.72026(9) 0.63625(7) 0.0186(3) Uani d 1 . .
C C14 0.34411(13) 0.74324(9) 0.52654(7) 0.0214(3) Uani d 1 . .
C C15 0.2548(2) 0.67935(14) 0.52089(12) 0.0622(8) Uani d 1 . .
H H15A 0.207089 0.683389 0.556308 0.093 Uiso calc 1 . .
H H15B 0.286095 0.623115 0.519003 0.093 Uiso calc 1 . .
H H15C 0.213484 0.690132 0.483698 0.093 Uiso calc 1 . .
C C16 0.4207(2) 0.73950(15) 0.47310(8) 0.0477(6) Uani d 1 . .
H H16A 0.480326 0.778580 0.479785 0.072 Uiso calc 1 . .
H H16B 0.382166 0.754898 0.435784 0.072 Uiso calc 1 . .
H H16C 0.449097 0.682580 0.469071 0.072 Uiso calc 1 . .
C C17 0.30051(15) 0.83103(10) 0.53339(7) 0.0292(4) Uani d 1 . .
H H17A 0.360098 0.869678 0.541516 0.044 Uiso calc 1 . .
H H17B 0.249301 0.832725 0.567338 0.044 Uiso calc 1 . .
H H17C 0.263853 0.847613 0.495754 0.044 Uiso calc 1 . .
C C18 0.43219(11) 0.75974(9) 0.78268(6) 0.0168(3) Uani d 1 . .
C C19 0.34560(12) 0.81251(9) 0.79479(7) 0.0192(3) Uani d 1 . .
H H19A 0.276094 0.798378 0.779861 0.023 Uiso calc 1 . .
C C20 0.35903(12) 0.88595(9) 0.82852(7) 0.0213(3) Uani d 1 . .
H H20A 0.299016 0.920984 0.836923 0.026 Uiso calc 1 . .
C C21 0.46028(12) 0.90708(9) 0.84950(7) 0.0192(3) Uani d 1 . .
C C22 0.54853(13) 0.85619(10) 0.83835(7) 0.0247(3) Uani d 1 . .
H H22A 0.618017 0.871002 0.852956 0.030 Uiso calc 1 . .
C C23 0.53307(12) 0.78277(10) 0.80522(7) 0.0229(3) Uani d 1 . .
H H23A 0.593071 0.747316 0.797753 0.028 Uiso calc 1 . .
C C24 0.55049(13) 1.00616(9) 0.91461(7) 0.0233(3) Uani d 1 . .
H H24A 0.535474 1.060914 0.934921 0.028 Uiso calc 1 . .
H H1N 0.6911(17) 0.6159(12) 0.6999(9) 0.030(5) 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'
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'
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
C24 O2 C21 . . 121.96(12) ?
C13 O4 C14 . . 122.42(12) ?
C9 N1 C1 . . 122.21(12) ?
C9 N1 H1N . . 117.9(13) ?
C1 N1 H1N . . 116.2(13) ?
C2 C1 N1 . . 119.02(13) ?
C2 C1 C10 . . 129.03(13) ?
N1 C1 C10 . . 111.95(12) ?
C1 C2 C13 . . 125.87(13) ?
C1 C2 C3 . . 119.37(12) ?
C13 C2 C3 . . 114.74(12) ?
C4 C3 C2 . . 109.63(11) ?
C4 C3 C18 . . 110.75(11) ?
C2 C3 C18 . . 111.59(11) ?
C4 C3 H3A . . 108.3 ?
C2 C3 H3A . . 108.3 ?
C18 C3 H3A . . 108.3 ?
C9 C4 C5 . . 120.75(13) ?
C9 C4 C3 . . 119.19(12) ?
C5 C4 C3 . . 119.94(12) ?
O1 C5 C4 . . 121.30(13) ?
O1 C5 C6 . . 119.73(13) ?
C4 C5 C6 . . 118.97(12) ?
C7A C6 C5 . . 111.51(19) ?
C12 C6 C5 . . 113.18(14) ?
C7A C6 C11A . . 114.0(3) ?
C5 C6 C11A . . 107.99(19) ?
C12 C6 C7 . . 109.13(15) ?
C5 C6 C7 . . 111.51(13) ?
C12 C6 C11 . . 109.71(17) ?
C5 C6 C11 . . 104.16(13) ?
C7 C6 C11 . . 108.97(16) ?
C7A C6 C12A . . 114.1(3) ?
C5 C6 C12A . . 101.5(2) ?
C11A C6 C12A . . 106.9(3) ?
C8 C7 C6 . . 112.2(4) ?
C8 C7 H7A . . 109.2 ?
C6 C7 H7A . . 109.2 ?
C8 C7 H7B . . 109.2 ?
C6 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
C9 C8 C7 . . 111.1(7) ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
C6 C11 H11A . . 109.5 ?
C6 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C6 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C6 C12 H12A . . 109.5 ?
C6 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C6 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C6 C7A C8A . . 112.7(8) ?
C6 C7A H7AA . . 109.0 ?
C8A C7A H7AA . . 109.0 ?
C6 C7A H7AB . . 109.0 ?
C8A C7A H7AB . . 109.0 ?
H7AA C7A H7AB . . 107.8 ?
C7A C8A C9 . . 110.2(11) ?
C7A C8A H8AA . . 109.6 ?
C9 C8A H8AA . . 109.6 ?
C7A C8A H8AB . . 109.6 ?
C9 C8A H8AB . . 109.6 ?
H8AA C8A H8AB . . 108.1 ?
C6 C11A H11D . . 109.5 ?
C6 C11A H11E . . 109.5 ?
H11D C11A H11E . . 109.5 ?
C6 C11A H11F . . 109.5 ?
H11D C11A H11F . . 109.5 ?
H11E C11A H11F . . 109.5 ?
C6 C12A H12D . . 109.5 ?
C6 C12A H12E . . 109.5 ?
H12D C12A H12E . . 109.5 ?
C6 C12A H12F . . 109.5 ?
H12D C12A H12F . . 109.5 ?
H12E C12A H12F . . 109.5 ?
C4 C9 N1 . . 119.68(13) ?
C4 C9 C8 . . 125.1(4) ?
N1 C9 C8 . . 115.2(4) ?
C4 C9 C8A . . 120.9(7) ?
N1 C9 C8A . . 119.4(7) ?
C1 C10 H10A . . 109.5 ?
C1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O3 C13 O4 . . 123.28(14) ?
O3 C13 C2 . . 122.98(14) ?
O4 C13 C2 . . 113.70(12) ?
O4 C14 C16 . . 102.37(13) ?
O4 C14 C17 . . 111.14(12) ?
C16 C14 C17 . . 109.82(14) ?
O4 C14 C15 . . 109.50(13) ?
C16 C14 C15 . . 111.71(19) ?
C17 C14 C15 . . 111.91(17) ?
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 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C19 C18 C23 . . 117.70(13) ?
C19 C18 C3 . . 121.64(13) ?
C23 C18 C3 . . 120.65(12) ?
C18 C19 C20 . . 121.21(14) ?
C18 C19 H19A . . 119.4 ?
C20 C19 H19A . . 119.4 ?
C21 C20 C19 . . 119.40(13) ?
C21 C20 H20A . . 120.3 ?
C19 C20 H20A . . 120.3 ?
C20 C21 C22 . . 121.11(14) ?
C20 C21 O2 . . 114.03(13) ?
C22 C21 O2 . . 124.86(14) ?
C21 C22 C23 . . 118.53(14) ?
C21 C22 H22A . . 120.7 ?
C23 C22 H22A . . 120.7 ?
C22 C23 C18 . . 122.05(14) ?
C22 C23 H23A . . 119.0 ?
C18 C23 H23A . . 119.0 ?
O2 C24 F2 . . 112.74(14) ?
O2 C24 F1 . . 111.38(12) ?
F2 C24 F1 . . 105.20(13) ?
O2 C24 H24A . . 109.1 ?
F2 C24 H24A . . 109.1 ?
F1 C24 H24A . . 109.1 ?
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 C24 . 1.3658(18) ?
F2 C24 . 1.3510(19) ?
O1 C5 . 1.2374(18) ?
O2 C24 . 1.3449(19) ?
O2 C21 . 1.4107(17) ?
O3 C13 . 1.2127(19) ?
O4 C13 . 1.3490(18) ?
O4 C14 . 1.4757(17) ?
N1 C9 . 1.3692(18) ?
N1 C1 . 1.3902(18) ?
N1 H1N . 0.88(2) ?
C1 C2 . 1.3578(19) ?
C1 C10 . 1.501(2) ?
C2 C13 . 1.470(2) ?
C2 C3 . 1.5273(19) ?
C3 C4 . 1.5132(18) ?
C3 C18 . 1.531(2) ?
C3 H3A . 1.0000 ?
C4 C9 . 1.364(2) ?
C4 C5 . 1.449(2) ?
C5 C6 . 1.5295(19) ?
C6 C7A . 1.447(4) ?
C6 C12 . 1.510(3) ?
C6 C11A . 1.546(5) ?
C6 C7 . 1.559(3) ?
C6 C11 . 1.560(3) ?
C6 C12A . 1.570(4) ?
C7 C8 . 1.547(10) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.468(11) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C7A C8A . 1.525(16) ?
C7A H7AA . 0.9900 ?
C7A H7AB . 0.9900 ?
C8A C9 . 1.553(18) ?
C8A H8AA . 0.9900 ?
C8A H8AB . 0.9900 ?
C11A H11D . 0.9800 ?
C11A H11E . 0.9800 ?
C11A H11F . 0.9800 ?
C12A H12D . 0.9800 ?
C12A H12E . 0.9800 ?
C12A H12F . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C14 C16 . 1.511(3) ?
C14 C17 . 1.512(2) ?
C14 C15 . 1.512(2) ?
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 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C19 . 1.3918(19) ?
C18 C23 . 1.396(2) ?
C19 C20 . 1.398(2) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.380(2) ?
C20 H20A . 0.9500 ?
C21 C22 . 1.386(2) ?
C22 C23 . 1.394(2) ?
C22 H22A . 0.9500 ?
C23 H23A . 0.9500 ?
C24 H24A . 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_657 0.88(2) 1.97(2) 2.8418(16) 171.2(19) yes
C8A H8A F2 8_755 0.99 2.53 3.168(19) 129.9 yes
C8AA H8AB F2 8_755 0.99 2.48 3.168(19) 126.2 yes
C10 H10A O4 . 0.98 2.27 2.7834(18) 111.7 yes
C15 H15A O3 . 0.98 2.47 3.038(3) 116.3 yes
C16 H16C F1 7_575 0.98 2.62 3.573(2) 164.4 yes
C17 H17B O3 . 0.98 2.41 2.969(2) 115.5 yes
C22 H22A F2 . 0.95 2.37 2.9091(19) 115.5 yes
C24 H24A O4 3_656 1.00 2.65 3.4638(18) 138.9 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 C2 . . . . 16.6(2) ?
C9 N1 C1 C10 . . . . -162.96(12) ?
N1 C1 C2 C13 . . . . -168.52(13) ?
C10 C1 C2 C13 . . . . 10.9(2) ?
N1 C1 C2 C3 . . . . 9.82(19) ?
C10 C1 C2 C3 . . . . -170.73(13) ?
C1 C2 C3 C4 . . . . -32.19(17) ?
C13 C2 C3 C4 . . . . 146.33(12) ?
C1 C2 C3 C18 . . . . 90.88(15) ?
C13 C2 C3 C18 . . . . -90.60(14) ?
C2 C3 C4 C9 . . . . 32.34(18) ?
C18 C3 C4 C9 . . . . -91.22(16) ?
C2 C3 C4 C5 . . . . -151.65(13) ?
C18 C3 C4 C5 . . . . 84.79(16) ?
C9 C4 C5 O1 . . . . -174.39(14) ?
C3 C4 C5 O1 . . . . 9.7(2) ?
C9 C4 C5 C6 . . . . 6.6(2) ?
C3 C4 C5 C6 . . . . -169.33(12) ?
O1 C5 C6 C7A . . . . -152.9(2) ?
C4 C5 C6 C7A . . . . 26.1(2) ?
O1 C5 C6 C12 . . . . 28.8(2) ?
C4 C5 C6 C12 . . . . -152.19(17) ?
O1 C5 C6 C11A . . . . -26.9(3) ?
C4 C5 C6 C11A . . . . 152.1(2) ?
O1 C5 C6 C7 . . . . 152.31(15) ?
C4 C5 C6 C7 . . . . -28.68(19) ?
O1 C5 C6 C11 . . . . -90.31(18) ?
C4 C5 C6 C11 . . . . 88.70(17) ?
O1 C5 C6 C12A . . . . 85.2(2) ?
C4 C5 C6 C12A . . . . -95.7(2) ?
C12 C6 C7 C8 . . . . 174.7(4) ?
C5 C6 C7 C8 . . . . 48.9(4) ?
C11 C6 C7 C8 . . . . -65.5(4) ?
C6 C7 C8 C9 . . . . -47.3(6) ?
C5 C6 C7A C8A . . . . -55.3(8) ?
C11A C6 C7A C8A . . . . -177.9(8) ?
C12A C6 C7A C8A . . . . 58.9(9) ?
C6 C7A C8A C9 . . . . 52.0(13) ?
C5 C4 C9 N1 . . . . 173.81(13) ?
C3 C4 C9 N1 . . . . -10.2(2) ?
C5 C4 C9 C8 . . . . -5.5(5) ?
C3 C4 C9 C8 . . . . 170.5(5) ?
C5 C4 C9 C8A . . . . -9.4(8) ?
C3 C4 C9 C8A . . . . 166.6(8) ?
C1 N1 C9 C4 . . . . -16.5(2) ?
C1 N1 C9 C8 . . . . 162.9(4) ?
C1 N1 C9 C8A . . . . 166.7(8) ?
C7 C8 C9 C4 . . . . 26.3(8) ?
C7 C8 C9 N1 . . . . -153.0(4) ?
C7A C8A C9 C4 . . . . -19.0(15) ?
C7A C8A C9 N1 . . . . 157.8(7) ?
C14 O4 C13 O3 . . . . -1.5(2) ?
C14 O4 C13 C2 . . . . 176.23(12) ?
C1 C2 C13 O3 . . . . -176.94(15) ?
C3 C2 C13 O3 . . . . 4.6(2) ?
C1 C2 C13 O4 . . . . 5.3(2) ?
C3 C2 C13 O4 . . . . -173.09(12) ?
C13 O4 C14 C16 . . . . 176.95(15) ?
C13 O4 C14 C17 . . . . 59.76(18) ?
C13 O4 C14 C15 . . . . -64.4(2) ?
C4 C3 C18 C19 . . . . -134.72(14) ?
C2 C3 C18 C19 . . . . 102.85(15) ?
C4 C3 C18 C23 . . . . 46.27(18) ?
C2 C3 C18 C23 . . . . -76.16(16) ?
C23 C18 C19 C20 . . . . -0.2(2) ?
C3 C18 C19 C20 . . . . -179.23(13) ?
C18 C19 C20 C21 . . . . 0.9(2) ?
C19 C20 C21 C22 . . . . -0.8(2) ?
C19 C20 C21 O2 . . . . 178.96(13) ?
C24 O2 C21 C20 . . . . 168.08(14) ?
C24 O2 C21 C22 . . . . -12.1(2) ?
C20 C21 C22 C23 . . . . 0.1(2) ?
O2 C21 C22 C23 . . . . -179.67(14) ?
C21 C22 C23 C18 . . . . 0.6(2) ?
C19 C18 C23 C22 . . . . -0.6(2) ?
C3 C18 C23 C22 . . . . 178.48(14) ?
C21 O2 C24 F2 . . . . 60.27(18) ?
C21 O2 C24 F1 . . . . -57.73(18) ?
