##############################################################################
#                                                                            #
# 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
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_journal_date_recd_electronic     2023-01-05
_journal_date_accepted     2023-02-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      3
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023001305
_journal_coeditor_code     DX2050
_publ_contact_author_name     'Yevhenii Vaksler'
_publ_contact_author_address
;
SSI "Institute for Single Crystals", National Academy of Sciences of Ukraine,
60
Nauky Ave, Kharkiv 61001,
Ukraine
;
_publ_contact_author_email     'vakslerea@gmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+380982813503'
_publ_section_title
;\
Synthesis, analysis of molecular and crystal structures, estimation of
intermolecular interactions and biological properties of
1-benzyl-6-fluoro-3-[5-(4-methylcyclohexyl)-1,2,4-oxadiazol-3-yl]-\
7-(piperidin-1-yl)quinolin-4-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Vaksler, Yevhenii' .
;
SSI "Institute for Single Crystals", National Academy of Sciences of Ukraine,
60 Nauky Ave, Kharkiv 61001,
Ukraine
;
    'Hryhoriv, Halyna V.' .
;
The National University of Pharmacy, 53 Pushkinska St, Kharkiv 61002,
Ukraine
;
    'Ivanov, Vladimir V.' .
;
V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61077,
Ukraine
;
    'Kovalenko, Sergiy M.' .
;
V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61077,
Ukraine
;
    'Georgiyants, Victoriya A.' .
;
The National University of Pharmacy, 53 Pushkinska St, Kharkiv 61002,
Ukraine
;
    'Langer, Thierry' .
;
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrabe 14,
A-1090, Vienna,
Austria
;
_publ_section_synopsis
;\
The synthesis of the potential antimicrobial and antiviral drug,
5-[1-benzyl-6-fluoro-7-(piperidin-1-yl)-quinolin-4(1H)-on-3-yl]-3-(4-\
methylcyclohex-1-yl)-1,2,4-oxadiazole, was proposed. Its molecular and
crystal structures were defined and described, whereas the biological activity
was predicted with molecular docking.
;
_chemical_name_systematic
; \
1-Benzyl-6-fluoro-3-[5-(4-methylcyclohexyl)-1,2,4-oxadiazol-3-yl]-\
7-(piperidin-1-yl)quinolin-4-one
;
_chemical_name_common
;\
5-[1-Benzyl-6-fluoro-7-(piperidin-1-yl)-quinolin-4(1H)-on-3-yl]-3-(4-\
methylcyclohex-1-yl)-1,2,4-oxadiazole
;
_chemical_formula_moiety     'C30 H33 F N4 O2, C3 H8 O'
_chemical_formula_sum     'C33 H41 F N4 O3'
_chemical_formula_iupac     'C30 H33 F N4 O2, C3 H8 O'
_chemical_formula_weight     560.70
_chemical_melting_point     476.15
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.9499(6)
_cell_length_b     11.2976(9)
_cell_length_c     14.9913(12)
_cell_angle_alpha     68.650(8)
_cell_angle_beta     89.473(6)
_cell_angle_gamma     78.976(6)
_cell_volume     1537.2(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2589
_cell_measurement_theta_min     3.9460
_cell_measurement_theta_max     28.2150
_cell_measurement_temperature     296.15
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.1
_exptl_crystal_density_diffrn     1.211
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_absorpt_correction_T_min     0.98623
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     296.15
_diffrn_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Xcalibur, Atlas'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'CCD plate'
_diffrn_detector_area_resol_mean     10.3779
_diffrn_reflns_number     14562
_diffrn_reflns_av_R_equivalents     0.0431
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_theta_min     3.421
_diffrn_reflns_theta_max     24.999
_diffrn_reflns_theta_full     24.999
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     17
_diffrn_radiation_probe     x-ray
_refine_special_details     ?
_reflns_number_total     5407
_reflns_number_gt     2707
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1435
_refine_ls_R_factor_gt     0.0661
_refine_ls_wR_factor_gt     0.1586
_refine_ls_wR_factor_ref     0.1892
_refine_ls_goodness_of_fit_ref     0.973
_refine_ls_restrained_S_all     0.990
_refine_ls_number_reflns     5407
_refine_ls_number_parameters     412
_refine_ls_number_restraints     54
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0881P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.297
_refine_diff_density_min     -0.242
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)'
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
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 0.40408(18) 0.53219(16) 1.12186(12) 0.0810(6) Uani d 1 . .
    O O1 -0.1510(2) 0.7148(3) 0.59426(15) 0.0918(7) Uani d 1 . .
    O O2 0.10050(19) 0.6960(2) 0.82423(13) 0.0688(6) Uani d 1 . .
    N N1 -0.0680(3) 0.6992(3) 0.67646(18) 0.0839(8) Uani d 1 . .
    N N2 -0.1356(3) 0.5139(3) 0.69218(17) 0.0729(7) Uani d 1 . .
    N N3 0.0757(2) 0.3148(2) 0.95995(15) 0.0535(6) Uani d 1 . .
    N N4 0.4118(2) 0.2672(2) 1.21202(14) 0.0543(6) Uani d 1 . .
    C C1 -0.1860(3) 0.6009(4) 0.6103(2) 0.0727(9) Uani d 1 . .
    C C2 -0.0628(3) 0.5791(3) 0.73033(19) 0.0595(8) Uani d 1 . .
    C C3 0.0080(3) 0.3883(3) 0.87466(19) 0.0564(7) Uani d 1 . .
    H H3 -0.047481 0.350041 0.848437 0.068 Uiso calc 1 . .
    C C4 0.0143(3) 0.5143(3) 0.82355(18) 0.0524(7) Uani d 1 . .
    C C5 0.0951(3) 0.5791(3) 0.86249(18) 0.0528(7) Uani d 1 . .
    C C6 0.2576(3) 0.5490(3) 0.99624(18) 0.0548(7) Uani d 1 . .
    H H6 0.263435 0.635774 0.967296 0.066 Uiso calc 1 . .
    C C7 0.3312(3) 0.4740(3) 1.07963(19) 0.0554(7) Uani d 1 . .
    C C8 0.3322(3) 0.3400(3) 1.12679(18) 0.0510(7) Uani d 1 . .
    C C9 0.2445(3) 0.2905(3) 1.08445(17) 0.0495(7) Uani d 1 . .
    H H9 0.239041 0.203628 1.113368 0.059 Uiso calc 1 . .
    C C10 0.1645(2) 0.3672(3) 0.99992(17) 0.0479(7) Uani d 1 . .
    C C11 0.1729(3) 0.4969(3) 0.95330(17) 0.0495(7) Uani d 1 . .
    C C12 0.5588(3) 0.2719(3) 1.21148(19) 0.0655(8) Uani d 1 . .
    H H12A 0.569509 0.360773 1.178841 0.079 Uiso calc 1 . .
    H H12B 0.605173 0.220547 1.176408 0.079 Uiso calc 1 . .
    C C13 0.6240(3) 0.2206(3) 1.3121(2) 0.0767(10) Uani d 1 . .
    H H13A 0.720944 0.222963 1.309746 0.092 Uiso calc 1 . .
    H H13B 0.581915 0.275375 1.345936 0.092 Uiso calc 1 . .
    C C14 0.6068(3) 0.0834(3) 1.3656(2) 0.0829(11) Uani d 1 . .
    H H14A 0.642767 0.054073 1.431599 0.100 Uiso calc 1 . .
    H H14B 0.657452 0.026422 1.336142 0.100 Uiso calc 1 . .
    C C15 0.4562(3) 0.0782(3) 1.3629(2) 0.0732(9) Uani d 1 . .
    H H15A 0.446362 -0.011460 1.392007 0.088 Uiso calc 1 . .
    H H15B 0.408760 0.125075 1.400558 0.088 Uiso calc 1 . .
    C C16 0.3905(3) 0.1353(3) 1.26275(19) 0.0602(8) Uani d 1 . .
    H H16A 0.428692 0.081034 1.227556 0.072 Uiso calc 1 . .
    H H16B 0.292786 0.136451 1.265326 0.072 Uiso calc 1 . .
    C C17 0.0544(3) 0.1821(3) 1.0101(2) 0.0596(8) Uani d 1 . .
    H H17A -0.029777 0.173344 0.983203 0.072 Uiso calc 1 . .
    H H17B 0.042178 0.168847 1.077120 0.072 Uiso calc 1 . .
    C C18 0.1692(3) 0.0775(3) 1.0047(2) 0.0613(8) Uani d 1 . .
    C C19 0.2007(4) -0.0381(3) 1.0801(3) 0.0839(10) Uani d 1 . .
    H H19 0.153116 -0.049765 1.135303 0.101 Uiso calc 1 . .
    C C20 0.3014(5) -0.1382(4) 1.0764(4) 0.1067(13) Uani d 1 . .
    H H20 0.319731 -0.216775 1.128258 0.128 Uiso calc 1 . .
    C C21 0.3726(5) -0.1226(5) 0.9984(5) 0.1236(16) Uani d 1 . .
    H H21 0.441061 -0.190020 0.996214 0.148 Uiso calc 1 . .
    C C22 0.3450(6) -0.0083(5) 0.9226(4) 0.150(2) Uani d 1 . .
    H H22 0.395091 0.002815 0.868434 0.180 Uiso calc 1 . .
    C C23 0.2423(5) 0.0921(4) 0.9254(3) 0.1159(15) Uani d 1 . .
    H H23 0.223190 0.169991 0.872837 0.139 Uiso calc 1 . .
    C C24 -0.2713(3) 0.5875(4) 0.5338(2) 0.0853(11) Uani d 1 . .
    H H24 -0.344876 0.544481 0.565601 0.102 Uiso calc 1 . .
    C C25 -0.1882(4) 0.5005(4) 0.4899(3) 0.1171(15) Uani d 1 . .
    H H25A -0.157137 0.415446 0.539389 0.141 Uiso calc 1 . .
    H H25B -0.107661 0.534888 0.464956 0.141 Uiso calc 1 . .
    C C26 -0.2665(4) 0.4864(4) 0.4101(3) 0.1127(14) Uani d 1 . .
    H H26A -0.205076 0.434701 0.381433 0.135 Uiso calc 1 . .
    H H26B -0.339078 0.440211 0.436824 0.135 Uiso calc 1 . .
    C C27 -0.3268(4) 0.6112(4) 0.3353(2) 0.0948(12) Uani d 1 . .
    H H27 -0.250641 0.653171 0.307528 0.114 Uiso calc 1 . .
    C C28 -0.4127(5) 0.6966(4) 0.3779(3) 0.1274(16) Uani d 1 . .
    H H28A -0.492846 0.660744 0.401895 0.153 Uiso calc 1 . .
    H H28B -0.444442 0.781228 0.328072 0.153 Uiso calc 1 . .
    C C29 -0.3383(5) 0.7134(4) 0.4595(3) 0.1212(15) Uani d 1 . .
    H H29A -0.269221 0.764582 0.433456 0.145 Uiso calc 1 . .
    H H29B -0.403422 0.760878 0.489193 0.145 Uiso calc 1 . .
    C C30 -0.4034(4) 0.5969(5) 0.2541(3) 0.1172(14) Uani d 1 . .
    H H30A -0.482705 0.561190 0.277632 0.176 Uiso calc 1 . .
    H H30B -0.344326 0.539912 0.229418 0.176 Uiso calc 1 . .
    H H30C -0.431828 0.680354 0.203884 0.176 Uiso calc 1 . .
    O O1A 0.9230(8) -0.0496(7) 0.7385(6) 0.090(2) Uani d 0.655(8) A 1
    H H1A 0.973132 -0.121327 0.762874 0.135 Uiso d 0.655(8) A 1
    C C1A 0.9840(10) 0.0330(8) 0.6585(6) 0.119(3) Uani d 0.655(8) A 1
    H H1AA 1.064792 -0.015019 0.639707 0.143 Uiso calc 0.655(8) A 1
    C C2A 0.8698(11) 0.0861(12) 0.5824(7) 0.189(5) Uani d 0.655(8) A 1
    H H2AA 0.845004 0.016382 0.568347 0.283 Uiso calc 0.655(8) A 1
    H H2AB 0.898808 0.146171 0.525414 0.283 Uiso calc 0.655(8) A 1
    H H2AC 0.791923 0.130018 0.604323 0.283 Uiso calc 0.655(8) A 1
    C C3A 1.0152(10) 0.1391(9) 0.6815(7) 0.195(5) Uani d 0.655(8) A 1
    H H3AA 0.936961 0.176312 0.707382 0.292 Uiso calc 0.655(8) A 1
    H H3AB 1.037392 0.204036 0.624393 0.292 Uiso calc 0.655(8) A 1
    H H3AC 1.091995 0.107152 0.728049 0.292 Uiso calc 0.655(8) A 1
    O O1B 0.957(2) -0.063(2) 0.7405(12) 0.153(7) Uani d 0.345(8) A 2
    H H1B 1.001248 -0.137151 0.766192 0.229 Uiso d 0.345(8) A 2
    C C1B 0.9053(17) 0.0324(15) 0.6486(10) 0.133(6) Uani d 0.345(8) A 2
    H H1BA 0.850989 -0.012521 0.622232 0.160 Uiso calc 0.345(8) A 2
    C C2B 1.0239(15) 0.0430(19) 0.5902(14) 0.186(9) Uani d 0.345(8) A 2
    H H2BA 1.003882 0.122132 0.534881 0.280 Uiso calc 0.345(8) A 2
    H H2BB 1.044114 -0.029514 0.569942 0.280 Uiso calc 0.345(8) A 2
    H H2BC 1.101692 0.043478 0.627413 0.280 Uiso calc 0.345(8) A 2
    C C3B 0.8059(16) 0.1510(13) 0.6445(11) 0.149(6) Uani d 0.345(8) A 2
    H H3BA 0.724542 0.126930 0.674673 0.223 Uiso calc 0.345(8) A 2
    H H3BB 0.782508 0.207177 0.578759 0.223 Uiso calc 0.345(8) A 2
    H H3BC 0.846576 0.195344 0.677535 0.223 Uiso calc 0.345(8) A 2
_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 C7 . 1.361(3) ?
    O1 N1 . 1.427(3) ?
    O1 C1 . 1.333(4) ?
    O2 C5 . 1.245(3) ?
    N1 C2 . 1.293(4) ?
    N2 C1 . 1.292(4) ?
    N2 C2 . 1.383(4) ?
    N3 C3 . 1.344(3) ?
    N3 C10 . 1.399(3) ?
    N3 C17 . 1.469(3) ?
    N4 C8 . 1.393(3) ?
    N4 C12 . 1.474(3) ?
    N4 C16 . 1.463(3) ?
    C1 C24 . 1.501(4) ?
    C2 C4 . 1.462(4) ?
    C3 H3 . 0.9300 ?
    C3 C4 . 1.363(4) ?
    C4 C5 . 1.439(4) ?
    C5 C11 . 1.462(4) ?
    C6 H6 . 0.9300 ?
    C6 C7 . 1.351(3) ?
    C6 C11 . 1.395(4) ?
    C7 C8 . 1.417(4) ?
    C8 C9 . 1.390(4) ?
    C9 H9 . 0.9300 ?
    C9 C10 . 1.395(3) ?
    C10 C11 . 1.394(4) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C12 C13 . 1.507(4) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C13 C14 . 1.506(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C14 C15 . 1.512(4) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C15 C16 . 1.499(4) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C17 C18 . 1.504(4) ?
    C18 C19 . 1.362(4) ?
    C18 C23 . 1.363(5) ?
    C19 H19 . 0.9300 ?
    C19 C20 . 1.377(5) ?
    C20 H20 . 0.9300 ?
    C20 C21 . 1.334(6) ?
    C21 H21 . 0.9300 ?
    C21 C22 . 1.355(6) ?
    C22 H22 . 0.9300 ?
    C22 C23 . 1.388(6) ?
    C23 H23 . 0.9300 ?
    C24 H24 . 0.9800 ?
    C24 C25 . 1.494(5) ?
    C24 C29 . 1.485(5) ?
    C25 H25A . 0.9700 ?
    C25 H25B . 0.9700 ?
    C25 C26 . 1.506(5) ?
    C26 H26A . 0.9700 ?
    C26 H26B . 0.9700 ?
    C26 C27 . 1.464(5) ?
    C27 H27 . 0.9800 ?
    C27 C28 . 1.481(5) ?
    C27 C30 . 1.515(5) ?
    C28 H28A . 0.9700 ?
    C28 H28B . 0.9700 ?
    C28 C29 . 1.523(5) ?
    C29 H29A . 0.9700 ?
    C29 H29B . 0.9700 ?
    C30 H30A . 0.9600 ?
    C30 H30B . 0.9600 ?
    C30 H30C . 0.9600 ?
    O1A H1A . 0.8200 ?
    O1A C1A . 1.438(8) ?
    C1A H1AA . 0.9800 ?
    C1A C2A . 1.489(9) ?
    C1A C3A . 1.448(10) ?
    C2A H2AA . 0.9600 ?
    C2A H2AB . 0.9600 ?
    C2A H2AC . 0.9600 ?
    C3A H3AA . 0.9600 ?
    C3A H3AB . 0.9600 ?
    C3A H3AC . 0.9600 ?
    O1B H1B . 0.8200 ?
    O1B C1B . 1.430(10) ?
    C1B H1BA . 0.9800 ?
    C1B C2B . 1.460(13) ?
    C1B C3B . 1.487(13) ?
    C2B H2BA . 0.9600 ?
    C2B H2BB . 0.9600 ?
    C2B H2BC . 0.9600 ?
    C3B H3BA . 0.9600 ?
    C3B H3BB . 0.9600 ?
    C3B H3BC . 0.9600 ?
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
    C1 O1 N1 . . 106.8(2) ?
    C2 N1 O1 . . 102.7(3) ?
    C1 N2 C2 . . 103.3(3) ?
    C3 N3 C10 . . 119.1(2) ?
    C3 N3 C17 . . 119.8(2) ?
    C10 N3 C17 . . 121.1(2) ?
    C8 N4 C12 . . 116.85(19) ?
    C8 N4 C16 . . 116.8(2) ?
    C16 N4 C12 . . 111.4(2) ?
    O1 C1 C24 . . 118.7(3) ?
    N2 C1 O1 . . 112.6(3) ?
    N2 C1 C24 . . 128.7(3) ?
    N1 C2 N2 . . 114.5(3) ?
    N1 C2 C4 . . 124.0(3) ?
    N2 C2 C4 . . 121.6(3) ?
    N3 C3 H3 . . 117.4 ?
    N3 C3 C4 . . 125.2(3) ?
    C4 C3 H3 . . 117.4 ?
    C3 C4 C2 . . 118.2(3) ?
    C3 C4 C5 . . 119.5(2) ?
    C5 C4 C2 . . 122.3(3) ?
    O2 C5 C4 . . 124.3(2) ?
    O2 C5 C11 . . 120.9(3) ?
    C4 C5 C11 . . 114.8(2) ?
    C7 C6 H6 . . 119.8 ?
    C7 C6 C11 . . 120.4(3) ?
    C11 C6 H6 . . 119.8 ?
    F1 C7 C8 . . 118.6(2) ?
    C6 C7 F1 . . 117.8(3) ?
    C6 C7 C8 . . 123.6(3) ?
    N4 C8 C7 . . 121.0(3) ?
    C9 C8 N4 . . 123.7(2) ?
    C9 C8 C7 . . 115.3(2) ?
    C8 C9 H9 . . 119.0 ?
    C8 C9 C10 . . 122.0(3) ?
    C10 C9 H9 . . 119.0 ?
    C9 C10 N3 . . 120.6(2) ?
    C11 C10 N3 . . 118.9(2) ?
    C11 C10 C9 . . 120.5(3) ?
    C6 C11 C5 . . 119.6(2) ?
    C10 C11 C5 . . 122.2(3) ?
    C10 C11 C6 . . 118.1(2) ?
    N4 C12 H12A . . 109.4 ?
    N4 C12 H12B . . 109.4 ?
    N4 C12 C13 . . 111.1(2) ?
    H12A C12 H12B . . 108.0 ?
    C13 C12 H12A . . 109.4 ?
    C13 C12 H12B . . 109.4 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 108.1 ?
    C14 C13 C12 . . 110.8(3) ?
    C14 C13 H13A . . 109.5 ?
    C14 C13 H13B . . 109.5 ?
    C13 C14 H14A . . 109.8 ?
    C13 C14 H14B . . 109.8 ?
    C13 C14 C15 . . 109.4(3) ?
    H14A C14 H14B . . 108.2 ?
    C15 C14 H14A . . 109.8 ?
    C15 C14 H14B . . 109.8 ?
    C14 C15 H15A . . 109.1 ?
    C14 C15 H15B . . 109.1 ?
    H15A C15 H15B . . 107.8 ?
    C16 C15 C14 . . 112.5(2) ?
    C16 C15 H15A . . 109.1 ?
    C16 C15 H15B . . 109.1 ?
    N4 C16 C15 . . 111.7(3) ?
    N4 C16 H16A . . 109.3 ?
    N4 C16 H16B . . 109.3 ?
    C15 C16 H16A . . 109.3 ?
    C15 C16 H16B . . 109.3 ?
    H16A C16 H16B . . 107.9 ?
    N3 C17 H17A . . 108.6 ?
    N3 C17 H17B . . 108.6 ?
    N3 C17 C18 . . 114.6(2) ?
    H17A C17 H17B . . 107.6 ?
    C18 C17 H17A . . 108.6 ?
    C18 C17 H17B . . 108.6 ?
    C19 C18 C17 . . 119.8(3) ?
    C19 C18 C23 . . 117.8(3) ?
    C23 C18 C17 . . 122.4(3) ?
    C18 C19 H19 . . 119.2 ?
    C18 C19 C20 . . 121.6(4) ?
    C20 C19 H19 . . 119.2 ?
    C19 C20 H20 . . 119.9 ?
    C21 C20 C19 . . 120.1(4) ?
    C21 C20 H20 . . 119.9 ?
    C20 C21 H21 . . 120.1 ?
    C20 C21 C22 . . 119.9(5) ?
    C22 C21 H21 . . 120.1 ?
    C21 C22 H22 . . 119.9 ?
    C21 C22 C23 . . 120.2(4) ?
    C23 C22 H22 . . 119.9 ?
    C18 C23 C22 . . 120.4(4) ?
    C18 C23 H23 . . 119.8 ?
    C22 C23 H23 . . 119.8 ?
    C1 C24 H24 . . 106.9 ?
    C25 C24 C1 . . 110.4(3) ?
    C25 C24 H24 . . 106.9 ?
    C29 C24 C1 . . 113.8(3) ?
    C29 C24 H24 . . 106.9 ?
    C29 C24 C25 . . 111.5(3) ?
    C24 C25 H25A . . 109.0 ?
    C24 C25 H25B . . 109.0 ?
    C24 C25 C26 . . 113.1(3) ?
    H25A C25 H25B . . 107.8 ?
    C26 C25 H25A . . 109.0 ?
    C26 C25 H25B . . 109.0 ?
    C25 C26 H26A . . 109.0 ?
    C25 C26 H26B . . 109.0 ?
    H26A C26 H26B . . 107.8 ?
    C27 C26 C25 . . 112.9(3) ?
    C27 C26 H26A . . 109.0 ?
    C27 C26 H26B . . 109.0 ?
    C26 C27 H27 . . 106.9 ?
    C26 C27 C28 . . 110.4(3) ?
    C26 C27 C30 . . 112.9(4) ?
    C28 C27 H27 . . 106.9 ?
    C28 C27 C30 . . 112.4(3) ?
    C30 C27 H27 . . 106.9 ?
    C27 C28 H28A . . 108.8 ?
    C27 C28 H28B . . 108.8 ?
    C27 C28 C29 . . 113.7(3) ?
    H28A C28 H28B . . 107.7 ?
    C29 C28 H28A . . 108.8 ?
    C29 C28 H28B . . 108.8 ?
    C24 C29 C28 . . 112.5(3) ?
    C24 C29 H29A . . 109.1 ?
    C24 C29 H29B . . 109.1 ?
    C28 C29 H29A . . 109.1 ?
    C28 C29 H29B . . 109.1 ?
    H29A C29 H29B . . 107.8 ?
    C27 C30 H30A . . 109.5 ?
    C27 C30 H30B . . 109.5 ?
    C27 C30 H30C . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    C1A O1A H1A . . 111.0 ?
    O1A C1A H1AA . . 112.1 ?
    O1A C1A C2A . . 102.5(8) ?
    O1A C1A C3A . . 109.0(8) ?
    C2A C1A H1AA . . 112.1 ?
    C3A C1A H1AA . . 112.1 ?
    C3A C1A C2A . . 108.4(9) ?
    C1A C2A H2AA . . 109.5 ?
    C1A C2A H2AB . . 109.5 ?
    C1A C2A H2AC . . 109.5 ?
    H2AA C2A H2AB . . 109.5 ?
    H2AA C2A H2AC . . 109.5 ?
    H2AB C2A H2AC . . 109.5 ?
    C1A C3A H3AA . . 109.5 ?
    C1A C3A H3AB . . 109.5 ?
    C1A C3A H3AC . . 109.5 ?
    H3AA C3A H3AB . . 109.5 ?
    H3AA C3A H3AC . . 109.5 ?
    H3AB C3A H3AC . . 109.5 ?
    C1B O1B H1B . . 141.8 ?
    O1B C1B H1BA . . 103.5 ?
    O1B C1B C2B . . 105.0(17) ?
    O1B C1B C3B . . 118.6(16) ?
    C2B C1B H1BA . . 103.5 ?
    C2B C1B C3B . . 120.3(15) ?
    C3B C1B H1BA . . 103.5 ?
    C1B C2B H2BA . . 109.5 ?
    C1B C2B H2BB . . 109.5 ?
    C1B C2B H2BC . . 109.5 ?
    H2BA C2B H2BB . . 109.5 ?
    H2BA C2B H2BC . . 109.5 ?
    H2BB C2B H2BC . . 109.5 ?
    C1B C3B H3BA . . 109.5 ?
    C1B C3B H3BB . . 109.5 ?
    C1B C3B H3BC . . 109.5 ?
    H3BA C3B H3BB . . 109.5 ?
    H3BA C3B H3BC . . 109.5 ?
    H3BB C3B H3BC . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    F1 C7 C8 N4 . . . . -3.4(4) ?
    F1 C7 C8 C9 . . . . 173.7(2) ?
    O1 N1 C2 N2 . . . . -0.7(3) ?
    O1 N1 C2 C4 . . . . 178.5(2) ?
    O1 C1 C24 C25 . . . . 110.5(4) ?
    O1 C1 C24 C29 . . . . -15.7(5) ?
    O2 C5 C11 C6 . . . . -2.0(4) ?
    O2 C5 C11 C10 . . . . 177.2(2) ?
    N1 O1 C1 N2 . . . . -0.3(4) ?
    N1 O1 C1 C24 . . . . -178.4(3) ?
    N1 C2 C4 C3 . . . . 178.0(3) ?
    N1 C2 C4 C5 . . . . -1.8(4) ?
    N2 C1 C24 C25 . . . . -67.3(5) ?
    N2 C1 C24 C29 . . . . 166.5(3) ?
    N2 C2 C4 C3 . . . . -2.8(4) ?
    N2 C2 C4 C5 . . . . 177.4(2) ?
    N3 C3 C4 C2 . . . . 178.2(2) ?
    N3 C3 C4 C5 . . . . -2.0(4) ?
    N3 C10 C11 C5 . . . . -1.9(4) ?
    N3 C10 C11 C6 . . . . 177.3(2) ?
    N3 C17 C18 C19 . . . . 146.5(3) ?
    N3 C17 C18 C23 . . . . -35.2(4) ?
    N4 C8 C9 C10 . . . . 178.8(2) ?
    N4 C12 C13 C14 . . . . 57.9(3) ?
    C1 O1 N1 C2 . . . . 0.6(3) ?
    C1 N2 C2 N1 . . . . 0.6(4) ?
    C1 N2 C2 C4 . . . . -178.7(3) ?
    C1 C24 C25 C26 . . . . -178.1(4) ?
    C1 C24 C29 C28 . . . . 174.5(4) ?
    C2 N2 C1 O1 . . . . -0.1(3) ?
    C2 N2 C1 C24 . . . . 177.7(3) ?
    C2 C4 C5 O2 . . . . 4.5(4) ?
    C2 C4 C5 C11 . . . . -175.9(2) ?
    C3 N3 C10 C9 . . . . -174.9(2) ?
    C3 N3 C10 C11 . . . . 4.4(4) ?
    C3 N3 C17 C18 . . . . 103.8(3) ?
    C3 C4 C5 O2 . . . . -175.3(2) ?
    C3 C4 C5 C11 . . . . 4.3(4) ?
    C4 C5 C11 C6 . . . . 178.3(2) ?
    C4 C5 C11 C10 . . . . -2.4(3) ?
    C6 C7 C8 N4 . . . . 179.0(2) ?
    C6 C7 C8 C9 . . . . -3.9(4) ?
    C7 C6 C11 C5 . . . . -179.3(2) ?
    C7 C6 C11 C10 . . . . 1.4(4) ?
    C7 C8 C9 C10 . . . . 1.8(4) ?
    C8 N4 C12 C13 . . . . 164.6(3) ?
    C8 N4 C16 C15 . . . . -166.8(2) ?
    C8 C9 C10 N3 . . . . -179.0(2) ?
    C8 C9 C10 C11 . . . . 1.7(4) ?
    C9 C10 C11 C5 . . . . 177.4(2) ?
    C9 C10 C11 C6 . . . . -3.3(4) ?
    C10 N3 C3 C4 . . . . -2.6(4) ?
    C10 N3 C17 C18 . . . . -76.8(3) ?
    C11 C6 C7 F1 . . . . -175.2(2) ?
    C11 C6 C7 C8 . . . . 2.4(4) ?
    C12 N4 C8 C7 . . . . -53.5(3) ?
    C12 N4 C8 C9 . . . . 129.7(3) ?
    C12 N4 C16 C15 . . . . 55.4(3) ?
    C12 C13 C14 C15 . . . . -55.0(4) ?
    C13 C14 C15 C16 . . . . 53.5(4) ?
    C14 C15 C16 N4 . . . . -54.0(4) ?
    C16 N4 C8 C7 . . . . 171.0(2) ?
    C16 N4 C8 C9 . . . . -5.8(4) ?
    C16 N4 C12 C13 . . . . -57.6(3) ?
    C17 N3 C3 C4 . . . . 176.8(2) ?
    C17 N3 C10 C9 . . . . 5.8(4) ?
    C17 N3 C10 C11 . . . . -174.9(2) ?
    C17 C18 C19 C20 . . . . 177.4(3) ?
    C17 C18 C23 C22 . . . . -178.3(4) ?
    C18 C19 C20 C21 . . . . 1.3(6) ?
    C19 C18 C23 C22 . . . . 0.1(6) ?
    C19 C20 C21 C22 . . . . -0.5(7) ?
    C20 C21 C22 C23 . . . . -0.5(8) ?
    C21 C22 C23 C18 . . . . 0.7(8) ?
    C23 C18 C19 C20 . . . . -1.0(5) ?
    C24 C25 C26 C27 . . . . 54.2(5) ?
    C25 C24 C29 C28 . . . . 48.9(5) ?
    C25 C26 C27 C28 . . . . -54.2(5) ?
    C25 C26 C27 C30 . . . . 179.0(4) ?
    C26 C27 C28 C29 . . . . 53.2(5) ?
    C27 C28 C29 C24 . . . . -51.5(6) ?
    C29 C24 C25 C26 . . . . -50.6(5) ?
    C30 C27 C28 C29 . . . . -179.7(4) ?
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
    C12 H12A F1 . 0.97 2.19 2.873(4) 126
    C16 H16B O1A 2_657 0.97 2.53 3.441(9) 155
    C17 H17B O1A 2_657 0.97 2.59 3.504(9) 157
    C17 H17B O1B 2_657 0.97 2.55 3.491(17) 162
    O1A H1A O2 1_645 0.82 2.09 2.906(9) 180
    O1B H1B O2 1_645 0.82 1.84 2.662(19) 180
_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     0.985
_shelx_estimated_absorpt_T_max     0.992
