##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2020-01-22
_journal_date_accepted     2020-03-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2020
_journal_volume     76
_journal_issue      4
_journal_page_first     567
_journal_page_last     571
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989020003837
_journal_coeditor_code     XI2021
_publ_contact_author_name     'Deepak Chopra'
_publ_contact_author_address
;
Department of Chemistry, Indian Institute of Science Education and Research
Bhopal,
Bhauri, Bhopal 462066, India
;
_publ_contact_author_email     'dchopra@iiserb.ac.in'
_publ_contact_author_fax     '9107556692392'
_publ_contact_author_phone     ?
_publ_section_title
;
Structural investigation of methyl
3-(4-fluorobenzoyl)-7-methyl-2-phenylindolizine-1-carboxylate, an inhibitory
drug towards Mycobacterium tuberculosis
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hasija, Avantika' .
;
Department of Chemistry,
Indian Institute of Science Education and Research Bhopal,
Bhauri, Bhopal 462066, India
;
    'Bhandary, Subhrajyoti' .
;
Department of Chemistry,
Indian Institute of Science Education and Research Bhopal,
Bhauri, Bhopal 462066, India
;
    'Venugopala, Katharigatta N.' .
;
Department of Pharmaceutical Sciences, College of Clinical Pharmacy,
King Faisal University, Al-Ahsa 31982, Kingdom of Saudi Arabia
Department of Biotechnology and Food Technology,
Durban University of Technology,
Durban 4001, South Africa
;
    'Sandeep Chandrashekharappa' .
;
Institute for Stem Cell Biology and Regenerative Medicine,
NCBS, TIFR, GKVK,
Bellary Road, Bangalore 560 065, India
;
    'Chopra, Deepak' .
;
Department of Chemistry,
Indian Institute of Science Education and Research Bhopal,
Bhauri, Bhopal 462066, India
;
_publ_section_synopsis
;
The structural analysis of a phenylindolizine-based drug, namely methyl
3-(4-flurobenzoyl)-7-methyl-2-phenylindolizine-1-carboxylate (I) was carried
out; this drug shows an inhibitory action towards mycobacterium
tuberculosis. The intermolecular interactions at play were characterized
via Hirshfeld surface analysis and fingerprint plots, highlighting the
evident role of C---H...O, C---H...F and C---H...π interactions in the
formation of the observed crystal structure.
;
_chemical_name_systematic
;
3-(4-Fluorobenzoyl)-7-methyl-2-phenylindolizine-1-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H18 F N O3'
_chemical_formula_sum     'C24 H18 F N O3'
_chemical_formula_iupac     'C24 H18 F N O3'
_chemical_formula_weight     387.39
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.3246(11)
_cell_length_b     9.8460(13)
_cell_length_c     25.837(4)
_cell_angle_alpha     90
_cell_angle_beta     93.318(3)
_cell_angle_gamma     90
_cell_volume     1860.2(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     27523
_cell_measurement_theta_min     2.21
_cell_measurement_theta_max     27.6
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.320
_exptl_crystal_size_mid     0.180
_exptl_crystal_size_min     0.040
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_F_000     808
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_absorpt_correction_T_min     0.855
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     173(2)
_diffrn_source     'fine-focus sealed tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker Kappa Duo APEXII'
_diffrn_measurement_method     '0.5° φ scans and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     27523
_diffrn_reflns_av_R_equivalents     0.0900
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_theta_min     2.214
_diffrn_reflns_theta_max     27.586
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_standards_number     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     4296
_reflns_number_gt     2641
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0990
_refine_ls_R_factor_gt     0.0499
_refine_ls_wR_factor_gt     0.1094
_refine_ls_wR_factor_ref     0.1305
_refine_ls_goodness_of_fit_ref     1.002
_refine_ls_restrained_S_all     1.002
_refine_ls_number_reflns     4296
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0555P)²+0.4550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.287
_refine_diff_density_min     -0.296
_refine_ls_extinction_method
;
SHELXL-2014/7 (Sheldrick 2015
;
_refine_ls_extinction_coef     0.0044(8)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
X-Seed (Barbour, 2001) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2020)
;
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 0.4480(2) 0.70181(14) 0.32107(5) 0.0563(4) Uani d 1 . .
    O O1 0.2787(2) 0.69998(15) 0.00174(6) 0.0381(4) Uani d 1 . .
    O O2 0.1668(2) 0.53237(14) -0.04937(5) 0.0302(4) Uani d 1 . .
    O O3 0.5350(2) 0.21447(15) 0.16777(5) 0.0336(4) Uani d 1 . .
    N N1 0.3494(2) 0.26669(16) 0.06884(6) 0.0230(4) Uani d 1 . .
    C C1 0.3588(3) 0.1276(2) 0.07210(8) 0.0293(5) Uani d 1 . .
    H H1 0.4025 0.0857 0.1035 0.035 Uiso calc 1 . .
    C C2 0.3057(3) 0.0502(2) 0.03060(8) 0.0294(5) Uani d 1 . .
    H H2 0.3148 -0.0459 0.0330 0.035 Uiso calc 1 . .
    C C3 0.2368(3) 0.1106(2) -0.01642(8) 0.0269(5) Uani d 1 . .
    C C4 0.2282(3) 0.2488(2) -0.01917(7) 0.0252(5) Uani d 1 . .
    H H4 0.1830 0.2906 -0.0505 0.030 Uiso calc 1 . .
    C C5 0.2850(3) 0.3307(2) 0.02346(7) 0.0232(4) Uani d 1 . .
    C C6 0.2913(3) 0.4722(2) 0.03281(7) 0.0232(4) Uani d 1 . .
    C C7 0.3565(3) 0.4924(2) 0.08437(7) 0.0225(4) Uani d 1 . .
    C C8 0.3910(3) 0.3647(2) 0.10738(7) 0.0229(4) Uani d 1 . .
    C C9 0.1754(3) 0.0225(2) -0.06142(8) 0.0356(5) Uani d 1 . .
    H H9A 0.1001 0.0760 -0.0865 0.053 Uiso calc 1 . .
    H H9B 0.1035 -0.0537 -0.0491 0.053 Uiso calc 1 . .
    H H9C 0.2826 -0.0125 -0.0781 0.053 Uiso calc 1 . .
    C C10 0.2478(3) 0.5806(2) -0.00470(7) 0.0248(5) Uani d 1 . .
    C C11 0.1182(3) 0.6340(2) -0.08794(8) 0.0315(5) Uani d 1 . .
    H H11A 0.0323 0.6988 -0.0739 0.047 Uiso calc 1 . .
    H H11B 0.0606 0.5902 -0.1188 0.047 Uiso calc 1 . .
    H H11C 0.2285 0.6822 -0.0974 0.047 Uiso calc 1 . .
    C C12 0.3881(3) 0.6250(2) 0.11063(7) 0.0250(5) Uani d 1 . .
    C C13 0.5610(3) 0.6581(2) 0.13180(7) 0.0287(5) Uani d 1 . .
    H H13 0.6610 0.5989 0.1269 0.034 Uiso calc 1 . .
    C C14 0.5889(3) 0.7767(2) 0.15993(8) 0.0363(6) Uani d 1 . .
    H H14 0.7076 0.7984 0.1743 0.044 Uiso calc 1 . .
    C C15 0.4445(4) 0.8634(2) 0.16707(8) 0.0387(6) Uani d 1 . .
    H H15 0.4631 0.9443 0.1867 0.046 Uiso calc 1 . .
    C C16 0.2724(4) 0.8320(2) 0.14543(8) 0.0390(6) Uani d 1 . .
    H H16 0.1729 0.8918 0.1502 0.047 Uiso calc 1 . .
    C C17 0.2443(3) 0.7144(2) 0.11693(8) 0.0326(5) Uani d 1 . .
    H H17 0.1263 0.6945 0.1016 0.039 Uiso calc 1 . .
    C C18 0.4633(3) 0.3265(2) 0.15900(7) 0.0253(5) Uani d 1 . .
    C C19 0.4534(3) 0.4247(2) 0.20269(7) 0.0257(5) Uani d 1 . .
    C C20 0.6087(3) 0.4441(2) 0.23563(8) 0.0324(5) Uani d 1 . .
    H H20 0.7157 0.3924 0.2307 0.039 Uiso calc 1 . .
    C C21 0.6082(3) 0.5381(2) 0.27542(8) 0.0385(6) Uani d 1 . .
    H H21 0.7144 0.5534 0.2975 0.046 Uiso calc 1 . .
    C C22 0.4491(4) 0.6086(2) 0.28191(8) 0.0374(6) Uani d 1 . .
    C C23 0.2923(3) 0.5899(2) 0.25163(8) 0.0328(5) Uani d 1 . .
    H H23 0.1843 0.6393 0.2579 0.039 Uiso calc 1 . .
    C C24 0.2955(3) 0.4967(2) 0.21143(8) 0.0283(5) Uani d 1 . .
    H H24 0.1883 0.4820 0.1897 0.034 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    F1 C22 . 1.367(2) ?
    O1 C10 . 1.206(2) ?
    O2 C10 . 1.353(2) ?
    O2 C11 . 1.442(2) ?
    O3 C18 . 1.236(2) ?
    N1 C1 . 1.373(3) ?
    N1 C5 . 1.389(2) ?
    N1 C8 . 1.408(2) ?
    C1 C2 . 1.354(3) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.419(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.364(3) ?
    C3 C9 . 1.499(3) ?
    C4 C5 . 1.409(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.414(3) ?
    C6 C7 . 1.403(3) ?
    C6 C10 . 1.465(3) ?
    C7 C8 . 1.407(3) ?
    C7 C12 . 1.483(3) ?
    C8 C18 . 1.456(3) ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 C13 . 1.389(3) ?
    C12 C17 . 1.389(3) ?
    C13 C14 . 1.384(3) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.380(3) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.384(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.382(3) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.491(3) ?
    C19 C24 . 1.387(3) ?
    C19 C20 . 1.393(3) ?
    C20 C21 . 1.383(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.375(3) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.364(3) ?
    C23 C24 . 1.388(3) ?
    C23 H23 . 0.9500 ?
    C24 H24 . 0.9500 ?
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
    C10 O2 C11 . . 115.09(16) ?
    C1 N1 C5 . . 121.17(17) ?
    C1 N1 C8 . . 129.22(17) ?
    C5 N1 C8 . . 109.56(16) ?
    C2 C1 N1 . . 120.09(19) ?
    C2 C1 H1 . . 120.0 ?
    N1 C1 H1 . . 120.0 ?
    C1 C2 C3 . . 120.92(19) ?
    C1 C2 H2 . . 119.5 ?
    C3 C2 H2 . . 119.5 ?
    C4 C3 C2 . . 118.41(18) ?
    C4 C3 C9 . . 121.74(19) ?
    C2 C3 C9 . . 119.85(18) ?
    C3 C4 C5 . . 121.33(19) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    N1 C5 C4 . . 118.07(18) ?
    N1 C5 C6 . . 107.26(16) ?
    C4 C5 C6 . . 134.66(18) ?
    C7 C6 C5 . . 107.94(17) ?
    C7 C6 C10 . . 125.01(18) ?
    C5 C6 C10 . . 126.97(17) ?
    C6 C7 C8 . . 108.49(17) ?
    C6 C7 C12 . . 126.51(17) ?
    C8 C7 C12 . . 124.99(17) ?
    C7 C8 N1 . . 106.72(16) ?
    C7 C8 C18 . . 131.69(18) ?
    N1 C8 C18 . . 121.52(17) ?
    C3 C9 H9A . . 109.5 ?
    C3 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C3 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O1 C10 O2 . . 121.96(18) ?
    O1 C10 C6 . . 125.95(18) ?
    O2 C10 C6 . . 112.09(17) ?
    O2 C11 H11A . . 109.5 ?
    O2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    O2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C13 C12 C17 . . 119.06(19) ?
    C13 C12 C7 . . 120.09(18) ?
    C17 C12 C7 . . 120.76(19) ?
    C14 C13 C12 . . 120.5(2) ?
    C14 C13 H13 . . 119.7 ?
    C12 C13 H13 . . 119.7 ?
    C15 C14 C13 . . 120.1(2) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C16 . . 119.7(2) ?
    C14 C15 H15 . . 120.2 ?
    C16 C15 H15 . . 120.2 ?
    C17 C16 C15 . . 120.4(2) ?
    C17 C16 H16 . . 119.8 ?
    C15 C16 H16 . . 119.8 ?
    C16 C17 C12 . . 120.2(2) ?
    C16 C17 H17 . . 119.9 ?
    C12 C17 H17 . . 119.9 ?
    O3 C18 C8 . . 121.78(18) ?
    O3 C18 C19 . . 118.57(17) ?
    C8 C18 C19 . . 119.64(17) ?
    C24 C19 C20 . . 119.31(19) ?
    C24 C19 C18 . . 122.16(18) ?
    C20 C19 C18 . . 118.54(19) ?
    C21 C20 C19 . . 120.6(2) ?
    C21 C20 H20 . . 119.7 ?
    C19 C20 H20 . . 119.7 ?
    C22 C21 C20 . . 117.8(2) ?
    C22 C21 H21 . . 121.1 ?
    C20 C21 H21 . . 121.1 ?
    C23 C22 F1 . . 118.3(2) ?
    C23 C22 C21 . . 123.6(2) ?
    F1 C22 C21 . . 118.1(2) ?
    C22 C23 C24 . . 117.9(2) ?
    C22 C23 H23 . . 121.0 ?
    C24 C23 H23 . . 121.0 ?
    C19 C24 C23 . . 120.7(2) ?
    C19 C24 H24 . . 119.6 ?
    C23 C24 H24 . . 119.6 ?
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
    C5 N1 C1 C2 . . . . 0.4(3) ?
    C8 N1 C1 C2 . . . . 177.53(19) ?
    N1 C1 C2 C3 . . . . -1.2(3) ?
    C1 C2 C3 C4 . . . . 1.2(3) ?
    C1 C2 C3 C9 . . . . -178.8(2) ?
    C2 C3 C4 C5 . . . . -0.4(3) ?
    C9 C3 C4 C5 . . . . 179.56(19) ?
    C1 N1 C5 C4 . . . . 0.4(3) ?
    C8 N1 C5 C4 . . . . -177.26(17) ?
    C1 N1 C5 C6 . . . . 179.55(18) ?
    C8 N1 C5 C6 . . . . 1.9(2) ?
    C3 C4 C5 N1 . . . . -0.4(3) ?
    C3 C4 C5 C6 . . . . -179.2(2) ?
    N1 C5 C6 C7 . . . . -1.1(2) ?
    C4 C5 C6 C7 . . . . 177.8(2) ?
    N1 C5 C6 C10 . . . . 175.82(18) ?
    C4 C5 C6 C10 . . . . -5.3(4) ?
    C5 C6 C7 C8 . . . . 0.0(2) ?
    C10 C6 C7 C8 . . . . -177.05(19) ?
    C5 C6 C7 C12 . . . . 178.88(19) ?
    C10 C6 C7 C12 . . . . 1.9(3) ?
    C6 C7 C8 N1 . . . . 1.2(2) ?
    C12 C7 C8 N1 . . . . -177.78(18) ?
    C6 C7 C8 C18 . . . . 178.3(2) ?
    C12 C7 C8 C18 . . . . -0.7(3) ?
    C1 N1 C8 C7 . . . . -179.3(2) ?
    C5 N1 C8 C7 . . . . -1.9(2) ?
    C1 N1 C8 C18 . . . . 3.2(3) ?
    C5 N1 C8 C18 . . . . -179.35(17) ?
    C11 O2 C10 O1 . . . . -1.0(3) ?
    C11 O2 C10 C6 . . . . 179.33(17) ?
    C7 C6 C10 O1 . . . . 7.9(3) ?
    C5 C6 C10 O1 . . . . -168.6(2) ?
    C7 C6 C10 O2 . . . . -172.44(18) ?
    C5 C6 C10 O2 . . . . 11.1(3) ?
    C6 C7 C12 C13 . . . . -121.3(2) ?
    C8 C7 C12 C13 . . . . 57.4(3) ?
    C6 C7 C12 C17 . . . . 62.2(3) ?
    C8 C7 C12 C17 . . . . -119.0(2) ?
    C17 C12 C13 C14 . . . . 1.7(3) ?
    C7 C12 C13 C14 . . . . -174.86(18) ?
    C12 C13 C14 C15 . . . . -0.2(3) ?
    C13 C14 C15 C16 . . . . -0.8(3) ?
    C14 C15 C16 C17 . . . . 0.2(3) ?
    C15 C16 C17 C12 . . . . 1.3(3) ?
    C13 C12 C17 C16 . . . . -2.2(3) ?
    C7 C12 C17 C16 . . . . 174.28(19) ?
    C7 C8 C18 O3 . . . . -157.8(2) ?
    N1 C8 C18 O3 . . . . 19.0(3) ?
    C7 C8 C18 C19 . . . . 21.5(3) ?
    N1 C8 C18 C19 . . . . -161.76(18) ?
    O3 C18 C19 C24 . . . . -134.5(2) ?
    C8 C18 C19 C24 . . . . 46.2(3) ?
    O3 C18 C19 C20 . . . . 45.5(3) ?
    C8 C18 C19 C20 . . . . -133.8(2) ?
    C24 C19 C20 C21 . . . . -2.6(3) ?
    C18 C19 C20 C21 . . . . 177.43(19) ?
    C19 C20 C21 C22 . . . . 1.4(3) ?
    C20 C21 C22 C23 . . . . 0.6(3) ?
    C20 C21 C22 F1 . . . . -179.8(2) ?
    F1 C22 C23 C24 . . . . 178.97(19) ?
    C21 C22 C23 C24 . . . . -1.4(3) ?
    C20 C19 C24 C23 . . . . 1.7(3) ?
    C18 C19 C24 C23 . . . . -178.30(19) ?
    C22 C23 C24 C19 . . . . 0.2(3) ?
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
    C1 H1 O3 1_555 0.95 2.26 2.853(3) 120
    C4 H4 O2 1_555 0.95 2.38 2.927(2) 116
    C21 H21 O3 2_655 0.95 2.54 3.399(3) 149
    C2 H2 O1 1_545 0.95 2.63 3.531(4) 157
    C15 H15 O3 1_565 0.95 2.76 3.519(4) 137
    C1 H1 C15 1_545 0.95 2.74 3.6064(3) 152
    C11 H11A C5 3_565 0.98 2.74 3.4906000 133
    C11 H11B F1 4_575 0.98 2.67 3.0585(3) 104
    C23 H23 O3 2_555 0.95 2.67 3.4875(3) 143
_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.
;
_shelx_estimated_absorpt_T_min     0.969
_shelx_estimated_absorpt_T_max     0.996
