##############################################################################
#                                                                            #
# 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.                                        #
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##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1490701'
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-06-08
_journal_date_accepted     2016-07-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2016
_journal_volume     72
_journal_issue      8
_journal_page_first     1081
_journal_page_last     1084
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989016010872
_journal_coeditor_code     ZS2365
_publ_contact_author_name     'Brahmi Jihed '
_publ_contact_author_address
;
Université de Monastir, Laboratoire de Synthèse Hétérocyclique
Produits Naturels et Réactivités, Faculté des Sciences de Monastir
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
_publ_contact_author_email     'jihedbrahmi85@live.fr'
_publ_contact_author_fax     '0021673500278'
_publ_contact_author_phone     '0021694799167'
_publ_section_title
;\
Crystal structure of
(1S,2S,2'R,3a'S,5R)-2'-[(5-bromo-\
1H-indol-3-yl)methyl]-2-isopropyl-5,5'-dimethyldihydro-2'H-\
spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ghannay, Siwar ' .
;
Université de Monastir, Laboratoire de Synthése Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
    'Brahmi, Jihed ' .
;
Université de Monastir, Laboratoire de Synthése Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
    'Nasri, Soumaya ' .
;
Laboratoire de Physico-chimie des Matériaux,
Faculté des Sciences de Monastir, Avenue de l'Environnement, 5019 Monastir,
University of Monastir, Tunisia
;
    'Aouadi, Kaïss ' .
;
Université de Monastir, Laboratoire de Synthése Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
    'Jeanneau, Erwann' .
;
Université Lyon 1, Centre de Diffractométrie Henri Longchambon,
Bâtiment 305, 43 boulevard du 11 Novembre 1918, F-69622 Villeurbanne Cedex,
France
;
    'Msaddek, Moncef' .
;
Université de Monastir, Laboratoire de Synthése Hétérocyclique,
Produits Naturels et Réactivités, Faculté des Sciences de Monastir,
Avenue de l'Environnement, 5000 Monastir, Tunisia
;
_publ_section_synopsis
;
The absolute structure for the title compound, which has five chiral centres has
been determined in this analysis. The supramolecular architecture comprises
parallel zigzag chains formed through N---H...N and C---H...O hydrogen bonds,
as well as intramolecular C---H...O, C---H...N and C---H...π interactions.
;
_chemical_name_systematic
;\
(1S,2S,2'R,3a'S,5R)-2'-[(5-Bromo-\
1H-indol-3-yl)methyl]-2-isopropyl-5,5'-dimethyldihydro-2'H-\
spiro[cyclohexane-1,6'-imidazo[1,5-b]isoxazol]-4'(5'H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H32 Br N3 O2'
_chemical_formula_sum     'C24 H32 Br N3 O2'
_chemical_formula_iupac     'C24 H32 Br N3 O2'
_chemical_formula_weight     474.43
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     10.2640(5)
_cell_length_b     9.6480(5)
_cell_length_c     12.0480(5)
_cell_angle_alpha     90
_cell_angle_beta     96.204(5)
_cell_angle_gamma     90
_cell_volume     1186.09(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8154
_cell_measurement_theta_min     0.998
_cell_measurement_theta_max     27.878
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.464
_exptl_crystal_size_mid     0.385
_exptl_crystal_size_min     0.112
_exptl_crystal_density_diffrn     1.328
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     1.757
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SCALEPACK; Otwinowski et al., 1997)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.455
_exptl_absorpt_correction_T_max     0.802
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
                            'Oxford Diffraction Xcalibur Atlas Gemini Ultra CCD'
_diffrn_measurement_method     'ω/2θ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10653
_diffrn_reflns_av_R_equivalents     0.1037
_diffrn_reflns_theta_min     2.711
_diffrn_reflns_theta_max     25.997
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details     ?
_reflns_number_total     4337
_reflns_number_gt     2924
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0892
_refine_ls_R_factor_gt     0.0529
_refine_ls_wR_factor_gt     0.1195
_refine_ls_wR_factor_ref     0.1351
_refine_ls_goodness_of_fit_ref     0.970
_refine_ls_restrained_S_all     0.970
_refine_ls_number_reflns     4337
_refine_ls_number_parameters     272
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.307
_refine_diff_density_min     -0.506
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1005 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack     -0.013(13)
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_structure_solution
;
SIR2011 (Burla et al., 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia,
2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
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
    Br Br 0.17985(7) 0.23216(8) 0.27079(6) 0.0716(3) Uani d 1 . .
    O O1 0.4307(4) 0.4046(5) 0.6482(4) 0.0455(11) Uani d 1 . .
    N N3 0.3297(6) 0.6276(6) 0.8208(5) 0.0559(16) Uani d 1 . .
    O O2 0.5063(6) 0.6393(6) 0.9554(4) 0.0728(16) Uani d 1 . .
    N N2 0.3578(5) 0.4065(6) 0.7471(4) 0.0419(12) Uani d 1 . .
    N N1 0.6516(6) 0.6022(6) 0.3324(5) 0.0521(15) Uani d 1 . .
    C C14 0.2644(7) 0.5267(7) 0.7427(5) 0.0447(15) Uani d 1 . .
    C C6 0.4147(7) 0.3475(8) 0.3841(6) 0.0472(16) Uani d 1 . .
    H H6 0.4007 0.2871 0.4418 0.057 Uiso calc 1 . .
    C C9 0.6468(6) 0.4016(8) 0.5952(5) 0.0478(16) Uani d 1 . .
    H H9A 0.7375 0.4153 0.6248 0.057 Uiso calc 1 . .
    H H9B 0.6317 0.3025 0.5885 0.057 Uiso calc 1 . .
    C C1 0.3301(7) 0.3486(8) 0.2869(6) 0.0523(18) Uani d 1 . .
    C C11 0.5918(7) 0.4126(9) 0.7977(6) 0.0513(18) Uani d 1 . .
    H H11A 0.6196 0.3164 0.8013 0.062 Uiso calc 1 . .
    H H11B 0.6594 0.4698 0.8372 0.062 Uiso calc 1 . .
    C C10 0.5591(6) 0.4605(7) 0.6774(5) 0.0426(15) Uani d 1 . .
    H H10 0.5572 0.5619 0.6734 0.051 Uiso calc 1 . .
    C C8 0.6248(6) 0.4659(7) 0.4806(5) 0.0439(15) Uani d 1 . .
    C C13 0.4388(7) 0.5769(8) 0.8831(6) 0.0523(18) Uani d 1 . .
    C C19 0.1319(7) 0.4750(8) 0.7834(5) 0.0485(17) Uani d 1 . .
    H H19 0.0774 0.5582 0.7854 0.058 Uiso calc 1 . .
    C C5 0.5213(6) 0.4378(7) 0.3948(5) 0.0428(15) Uani d 1 . .
    C C12 0.4609(6) 0.4315(8) 0.8439(5) 0.0471(16) Uani d 1 . .
    H H12 0.4518 0.3648 0.9039 0.057 Uiso calc 1 . .
    C C16 0.1585(6) 0.4977(7) 0.5389(5) 0.0472(16) Uani d 1 . .
    H H16 0.2112 0.4153 0.5275 0.057 Uiso calc 1 . .
    C C15 0.2358(7) 0.5914(7) 0.6262(6) 0.0500(17) Uani d 1 . .
    H H15A 0.3184 0.6159 0.5992 0.060 Uiso calc 1 . .
    H H15B 0.1867 0.6764 0.6328 0.060 Uiso calc 1 . .
    C C7 0.6991(6) 0.5668(8) 0.4386(6) 0.0503(17) Uani d 1 . .
    H H7 0.7730 0.6064 0.4776 0.060 Uiso calc 1 . .
    C C4 0.5407(7) 0.5268(7) 0.3039(6) 0.0459(16) Uani d 1 . .
    C C18 0.0585(7) 0.3816(8) 0.6964(6) 0.0544(18) Uani d 1 . .
    H H18A -0.0241 0.3541 0.7220 0.065 Uiso calc 1 . .
    H H18B 0.1096 0.2983 0.6884 0.065 Uiso calc 1 . .
    C C3 0.4561(8) 0.5248(8) 0.2046(6) 0.056(2) Uani d 1 . .
    H H3 0.4705 0.5828 0.1455 0.068 Uiso calc 1 . .
    C C17 0.0316(6) 0.4521(9) 0.5829(6) 0.0574(19) Uani d 1 . .
    H H17A -0.0146 0.3883 0.5302 0.069 Uiso calc 1 . .
    H H17B -0.0241 0.5322 0.5896 0.069 Uiso calc 1 . .
    C C21 0.1702(8) 0.2603(9) 0.9120(6) 0.071(2) Uani d 1 . .
    H H21A 0.2474 0.2388 0.8770 0.107 Uiso calc 1 . .
    H H21B 0.1833 0.2340 0.9892 0.107 Uiso calc 1 . .
    H H21C 0.0968 0.2105 0.8754 0.107 Uiso calc 1 . .
    C C2 0.3522(8) 0.4357(8) 0.1965(6) 0.061(2) Uani d 1 . .
    H H2 0.2954 0.4324 0.1309 0.073 Uiso calc 1 . .
    C C20 0.1432(7) 0.4168(9) 0.9030(6) 0.0554(18) Uani d 1 . .
    H H20 0.2168 0.4641 0.9457 0.066 Uiso calc 1 . .
    C C23 0.1317(8) 0.5741(9) 0.4278(6) 0.068(2) Uani d 1 . .
    H H23A 0.2133 0.6015 0.4022 0.102 Uiso calc 1 . .
    H H23B 0.0854 0.5139 0.3736 0.102 Uiso calc 1 . .
    H H23C 0.0796 0.6549 0.4376 0.102 Uiso calc 1 . .
    C C22 0.0205(10) 0.4502(13) 0.9589(8) 0.097(3) Uani d 1 . .
    H H22A 0.0032 0.5479 0.9535 0.145 Uiso calc 1 . .
    H H22B -0.0527 0.4001 0.9222 0.145 Uiso calc 1 . .
    H H22C 0.0338 0.4236 1.0361 0.145 Uiso calc 1 . .
    C C24 0.2777(9) 0.7638(8) 0.8427(8) 0.081(3) Uani d 1 . .
    H H24A 0.2015 0.7815 0.7912 0.121 Uiso calc 1 . .
    H H24B 0.2542 0.7668 0.9177 0.121 Uiso calc 1 . .
    H H24C 0.3431 0.8329 0.8338 0.121 Uiso calc 1 . .
    H HN1 0.6758 0.6699 0.2885 0.07(2) Uiso d 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
    Br C1 . 1.901(7) ?
    O1 C10 . 1.432(7) ?
    O1 N2 . 1.475(6) ?
    N3 C13 . 1.369(10) ?
    N3 C24 . 1.453(10) ?
    N3 C14 . 1.465(9) ?
    O2 C13 . 1.212(9) ?
    N2 C14 . 1.502(9) ?
    N2 C12 . 1.507(8) ?
    N1 C7 . 1.362(9) ?
    N1 C4 . 1.362(9) ?
    N1 HN1 . 0.8929 ?
    C14 C15 . 1.535(9) ?
    C14 C19 . 1.576(10) ?
    C6 C1 . 1.381(10) ?
    C6 C5 . 1.394(10) ?
    C6 H6 . 0.9300 ?
    C9 C8 . 1.508(9) ?
    C9 C10 . 1.519(9) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C1 C2 . 1.413(11) ?
    C11 C12 . 1.519(9) ?
    C11 C10 . 1.524(9) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C10 H10 . 0.9800 ?
    C8 C7 . 1.368(9) ?
    C8 C5 . 1.426(9) ?
    C13 C12 . 1.506(11) ?
    C19 C18 . 1.519(10) ?
    C19 C20 . 1.540(10) ?
    C19 H19 . 0.9800 ?
    C5 C4 . 1.423(9) ?
    C12 H12 . 0.9800 ?
    C16 C17 . 1.523(10) ?
    C16 C23 . 1.526(10) ?
    C16 C15 . 1.540(10) ?
    C16 H16 . 0.9800 ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C7 H7 . 0.9300 ?
    C4 C3 . 1.401(11) ?
    C18 C17 . 1.526(10) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C3 C2 . 1.365(11) ?
    C3 H3 . 0.9300 ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C21 C20 . 1.537(12) ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C2 H2 . 0.9300 ?
    C20 C22 . 1.525(10) ?
    C20 H20 . 0.9800 ?
    C23 H23A . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23C . 0.9600 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 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
    C10 O1 N2 . . 109.3(4) ?
    C13 N3 C24 . . 121.2(7) ?
    C13 N3 C14 . . 113.9(6) ?
    C24 N3 C14 . . 124.5(7) ?
    O1 N2 C14 . . 111.0(5) ?
    O1 N2 C12 . . 104.6(4) ?
    C14 N2 C12 . . 107.2(5) ?
    C7 N1 C4 . . 107.9(6) ?
    C7 N1 HN1 . . 130.2 ?
    C4 N1 HN1 . . 121.3 ?
    N3 C14 N2 . . 104.1(5) ?
    N3 C14 C15 . . 110.2(5) ?
    N2 C14 C15 . . 113.9(5) ?
    N3 C14 C19 . . 111.1(5) ?
    N2 C14 C19 . . 108.3(5) ?
    C15 C14 C19 . . 109.1(5) ?
    C1 C6 C5 . . 119.2(6) ?
    C1 C6 H6 . . 120.4 ?
    C5 C6 H6 . . 120.4 ?
    C8 C9 C10 . . 113.7(5) ?
    C8 C9 H9A . . 108.8 ?
    C10 C9 H9A . . 108.8 ?
    C8 C9 H9B . . 108.8 ?
    C10 C9 H9B . . 108.8 ?
    H9A C9 H9B . . 107.7 ?
    C6 C1 C2 . . 121.4(7) ?
    C6 C1 Br . . 120.7(6) ?
    C2 C1 Br . . 117.9(6) ?
    C12 C11 C10 . . 101.5(5) ?
    C12 C11 H11A . . 111.5 ?
    C10 C11 H11A . . 111.5 ?
    C12 C11 H11B . . 111.5 ?
    C10 C11 H11B . . 111.5 ?
    H11A C11 H11B . . 109.3 ?
    O1 C10 C9 . . 107.0(5) ?
    O1 C10 C11 . . 102.8(5) ?
    C9 C10 C11 . . 114.9(5) ?
    O1 C10 H10 . . 110.6 ?
    C9 C10 H10 . . 110.6 ?
    C11 C10 H10 . . 110.6 ?
    C7 C8 C5 . . 105.6(6) ?
    C7 C8 C9 . . 126.7(6) ?
    C5 C8 C9 . . 127.7(6) ?
    O2 C13 N3 . . 125.9(8) ?
    O2 C13 C12 . . 126.4(7) ?
    N3 C13 C12 . . 107.6(6) ?
    C18 C19 C20 . . 114.3(6) ?
    C18 C19 C14 . . 110.7(6) ?
    C20 C19 C14 . . 115.3(6) ?
    C18 C19 H19 . . 105.2 ?
    C20 C19 H19 . . 105.2 ?
    C14 C19 H19 . . 105.2 ?
    C6 C5 C4 . . 118.7(6) ?
    C6 C5 C8 . . 134.6(6) ?
    C4 C5 C8 . . 106.7(6) ?
    C13 C12 N2 . . 105.9(6) ?
    C13 C12 C11 . . 113.3(6) ?
    N2 C12 C11 . . 105.8(5) ?
    C13 C12 H12 . . 110.5 ?
    N2 C12 H12 . . 110.5 ?
    C11 C12 H12 . . 110.5 ?
    C17 C16 C23 . . 111.4(6) ?
    C17 C16 C15 . . 109.2(6) ?
    C23 C16 C15 . . 110.3(6) ?
    C17 C16 H16 . . 108.6 ?
    C23 C16 H16 . . 108.6 ?
    C15 C16 H16 . . 108.6 ?
    C14 C15 C16 . . 114.8(5) ?
    C14 C15 H15A . . 108.6 ?
    C16 C15 H15A . . 108.6 ?
    C14 C15 H15B . . 108.6 ?
    C16 C15 H15B . . 108.6 ?
    H15A C15 H15B . . 107.5 ?
    N1 C7 C8 . . 111.6(6) ?
    N1 C7 H7 . . 124.2 ?
    C8 C7 H7 . . 124.2 ?
    N1 C4 C3 . . 130.3(7) ?
    N1 C4 C5 . . 108.1(6) ?
    C3 C4 C5 . . 121.6(7) ?
    C19 C18 C17 . . 112.5(6) ?
    C19 C18 H18A . . 109.1 ?
    C17 C18 H18A . . 109.1 ?
    C19 C18 H18B . . 109.1 ?
    C17 C18 H18B . . 109.1 ?
    H18A C18 H18B . . 107.8 ?
    C2 C3 C4 . . 118.5(7) ?
    C2 C3 H3 . . 120.7 ?
    C4 C3 H3 . . 120.7 ?
    C16 C17 C18 . . 111.2(5) ?
    C16 C17 H17A . . 109.4 ?
    C18 C17 H17A . . 109.4 ?
    C16 C17 H17B . . 109.4 ?
    C18 C17 H17B . . 109.4 ?
    H17A C17 H17B . . 108.0 ?
    C20 C21 H21A . . 109.5 ?
    C20 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C20 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C3 C2 C1 . . 120.5(7) ?
    C3 C2 H2 . . 119.7 ?
    C1 C2 H2 . . 119.7 ?
    C22 C20 C21 . . 109.1(8) ?
    C22 C20 C19 . . 110.7(7) ?
    C21 C20 C19 . . 114.7(6) ?
    C22 C20 H20 . . 107.3 ?
    C21 C20 H20 . . 107.3 ?
    C19 C20 H20 . . 107.3 ?
    C16 C23 H23A . . 109.5 ?
    C16 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C16 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C20 C22 H22A . . 109.5 ?
    C20 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C20 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    N3 C24 H24A . . 109.5 ?
    N3 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    N3 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 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
    C10 O1 N2 C12 . . . . -14.5(6) no
    C10 O1 N2 C14 . . . . 100.9(5) no
    N2 O1 C10 C9 . . . . 155.8(5) no
    N2 O1 C10 C11 . . . . 34.4(6) no
    C7 N1 C4 C3 . . . . -179.9(8) no
    C7 N1 C4 C5 . . . . -2.0(8) no
    C4 N1 C7 C8 . . . . 2.0(8) no
    O1 N2 C12 C11 . . . . -11.6(7) no
    O1 N2 C12 C13 . . . . 109.0(5) no
    C14 N2 C12 C11 . . . . -129.6(6) no
    C14 N2 C12 C13 . . . . -9.0(6) no
    O1 N2 C14 N3 . . . . -103.0(5) no
    O1 N2 C14 C15 . . . . 17.2(7) no
    O1 N2 C14 C19 . . . . 138.7(5) no
    C12 N2 C14 N3 . . . . 10.8(6) no
    C12 N2 C14 C15 . . . . 130.9(6) no
    C12 N2 C14 C19 . . . . -107.6(5) no
    C14 N3 C13 O2 . . . . -177.5(7) no
    C14 N3 C13 C12 . . . . 3.6(8) no
    C24 N3 C13 O2 . . . . -4.7(12) no
    C24 N3 C13 C12 . . . . 176.5(6) no
    C13 N3 C14 N2 . . . . -9.2(7) no
    C13 N3 C14 C15 . . . . -131.7(6) no
    C13 N3 C14 C19 . . . . 107.2(7) no
    C24 N3 C14 N2 . . . . 178.3(6) no
    C24 N3 C14 C15 . . . . 55.8(9) no
    C24 N3 C14 C19 . . . . -65.3(8) no
    Br C1 C2 C3 . . . . 177.9(6) no
    C6 C1 C2 C3 . . . . -2.2(12) no
    Br C1 C6 C5 . . . . -177.7(5) no
    C2 C1 C6 C5 . . . . 2.4(11) no
    C1 C2 C3 C4 . . . . 0.6(12) no
    C2 C3 C4 N1 . . . . 178.3(7) no
    C2 C3 C4 C5 . . . . 0.7(11) no
    N1 C4 C5 C6 . . . . -178.5(6) no
    N1 C4 C5 C8 . . . . 1.3(8) no
    C3 C4 C5 C6 . . . . -0.4(10) no
    C3 C4 C5 C8 . . . . 179.4(7) no
    C4 C5 C6 C1 . . . . -1.1(10) no
    C8 C5 C6 C1 . . . . 179.1(7) no
    C4 C5 C8 C7 . . . . -0.1(7) no
    C4 C5 C8 C9 . . . . 178.3(6) no
    C6 C5 C8 C7 . . . . 179.7(8) no
    C6 C5 C8 C9 . . . . -1.9(13) no
    N1 C7 C8 C5 . . . . -1.2(8) no
    N1 C7 C8 C9 . . . . -179.6(6) no
    C5 C8 C9 C10 . . . . -78.1(9) no
    C7 C8 C9 C10 . . . . 100.1(8) no
    C8 C9 C10 O1 . . . . 74.7(7) no
    C8 C9 C10 C11 . . . . -171.8(6) no
    O1 C10 C11 C12 . . . . -39.7(7) no
    C9 C10 C11 C12 . . . . -155.6(6) no
    C10 C11 C12 N2 . . . . 31.3(7) no
    C10 C11 C12 C13 . . . . -84.4(7) no
    N2 C12 C13 O2 . . . . -175.3(7) no
    N2 C12 C13 N3 . . . . 3.5(7) no
    C11 C12 C13 O2 . . . . -59.8(10) no
    C11 C12 C13 N3 . . . . 119.1(6) no
    N2 C14 C15 C16 . . . . 67.4(8) no
    N3 C14 C15 C16 . . . . -176.0(6) no
    C19 C14 C15 C16 . . . . -53.7(7) no
    N2 C14 C19 C18 . . . . -71.8(7) no
    N2 C14 C19 C20 . . . . 59.8(7) no
    N3 C14 C19 C18 . . . . 174.4(6) no
    N3 C14 C19 C20 . . . . -54.0(8) no
    C15 C14 C19 C18 . . . . 52.6(7) no
    C15 C14 C19 C20 . . . . -175.8(6) no
    C14 C15 C16 C17 . . . . 55.4(8) no
    C14 C15 C16 C23 . . . . 178.1(6) no
    C15 C16 C17 C18 . . . . -55.5(8) no
    C23 C16 C17 C18 . . . . -177.4(6) no
    C16 C17 C18 C19 . . . . 58.6(8) no
    C17 C18 C19 C14 . . . . -56.6(8) no
    C17 C18 C19 C20 . . . . 171.3(6) no
    C14 C19 C20 C21 . . . . -89.9(8) no
    C14 C19 C20 C22 . . . . 146.0(7) no
    C18 C19 C20 C21 . . . . 40.0(9) no
    C18 C19 C20 C22 . . . . -84.1(9) no
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 HN1 N2 2_656 0.89 2.34 3.087(8) 141 yes
    C3 H3 O2 1_554 0.93 2.42 3.292(9) 156 yes
    C16 H16 O1 1_555 0.98 2.55 3.091(8) 115 yes
    C20 H20 N3 1_555 0.98 2.54 3.032(10) 111 yes
    C21 H21A N2 1_555 0.96 2.60 3.236(9) 124 yes
    N1 HN1 O1 2_656 0.89 2.66 3.053(8) 108 yes
    C20 H20 Cg3 1_555 0.98 2.41 2.866(8) 104 yes
