##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
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data_global
_audit_creation_method     'APEX3 v2017.3-0'
_journal_date_recd_electronic     2018-01-08
_journal_date_accepted     2018-01-09
_journal_name_full     'IUCrData'
_journal_year     2018
_journal_volume     3
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314618000573
_journal_coeditor_code     VM4032
_publ_contact_author_name     'Youssef Ramli'
_publ_contact_author_address
;
Laboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy,
Mohammed V University, Rabat
Morocco
;
_publ_contact_author_email     'y.ramli@um5s.net.ma'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
3-Hexyl-5,5-diphenylimidazolidine-2,4-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Guerrab, Walid' .
;
Laboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy,
Mohammed V University, Rabat
Morocco
;
    'Mague, Joel T' .
;
Department of Chemistry, Tulane University, New Orleans, LA 70118,
USA
;
    'Taoufik, Jamal' .
;
Laboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy,
Mohammed V University, Rabat
Morocco
;
    'Ramli, Youssef' .
;
Laboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy,
Mohammed V University, Rabat
Morocco
;
_publ_section_synopsis
;
The two independent molecules in the asymmetric unit differ in the orientations
of the hexyl and phenyl substituents on the imidazolidine-2,4-dione ring. In
the crystal, C---H...O hydrogen bonds between independent molecules form
chains along the a-axis direction, which are bound into ribbons by
paired N---H...O hydrogen bonds. Additional C---H...O hydrogen bonds and
C---H...π(ring) interactions tie the ribbons into a three-dimensional
structure.
;
data_I
_audit_creation_method     'SHELXL-2016/6'
_chemical_name_systematic
;
3-Hexyl-5,5-diphenylimidazolidine-2,4-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H24 N2 O2'
_chemical_formula_sum     'C21 H24 N2 O2'
_chemical_formula_iupac     'C21 H24 N2 O2'
_chemical_formula_weight     336.42
_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     8.5395(13)
_cell_length_b     8.9377(13)
_cell_length_c     23.444(4)
_cell_angle_alpha     90
_cell_angle_beta     91.066(2)
_cell_angle_gamma     90
_cell_volume     1789.0(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9959
_cell_measurement_theta_min     2.4388
_cell_measurement_theta_max     28.9891
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.268
_exptl_crystal_size_mid     0.216
_exptl_crystal_size_min     0.163
_exptl_crystal_density_diffrn     1.249
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_shelx_estimated_absorpt_T_min     0.979
_shelx_estimated_absorpt_T_max     0.987
_exptl_absorpt_correction_T_min     0.87
_exptl_absorpt_correction_T_max     0.99
_exptl_special_details
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, colllected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 20 sec/frame.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     34684
_diffrn_reflns_av_R_equivalents     0.0431
_diffrn_reflns_theta_min     1.738
_diffrn_reflns_theta_max     29.205
_diffrn_reflns_theta_full     29.000
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -31
_diffrn_reflns_limit_l_max     32
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. Refined as a 2-component
inversion twin. H-atoms were placed in calculated positions (C---H =
0.95 - 0.99 Å; N---H = 0.88 Å). All were included as riding contributions
with isotropic displacement parameters 1.2 - 1.5 times those of the attached
atoms.
;
_reflns_number_total     9382
_reflns_number_gt     7808
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0549
_refine_ls_R_factor_gt     0.0444
_refine_ls_wR_factor_gt     0.1075
_refine_ls_wR_factor_ref     0.1119
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     9382
_refine_ls_number_parameters     454
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0634P)²] 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     0.346
_refine_diff_density_min     -0.225
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Refined as an inversion twin
;
_refine_ls_abs_structure_Flack     0.2(10)
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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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
    O O1 0.36738(17) 0.13246(19) 0.08478(6) 0.0250(4) Uani d 1 . .
    O O2 0.54242(17) -0.05628(19) 0.25579(6) 0.0235(4) Uani d 1 . .
    N N1 0.41641(19) 0.0240(2) 0.17241(7) 0.0192(4) Uani d 1 . .
    N N2 0.6629(2) 0.0916(2) 0.18873(7) 0.0194(4) Uani d 1 . .
    H H2 0.753310 0.105054 0.206598 0.023 Uiso calc 1 . .
    C C1 0.6269(2) 0.1530(2) 0.13210(8) 0.0173(4) Uani d 1 . .
    C C2 0.4539(2) 0.1042(3) 0.12497(9) 0.0194(4) Uani d 1 . .
    C C3 0.5447(2) 0.0128(3) 0.21078(8) 0.0186(4) Uani d 1 . .
    C C4 0.2645(2) -0.0477(3) 0.18156(9) 0.0199(4) Uani d 1 . .
    H H4A 0.179794 0.022126 0.169864 0.024 Uiso calc 1 . .
    H H4B 0.253265 -0.068787 0.222740 0.024 Uiso calc 1 . .
    C C5 0.2463(3) -0.1920(3) 0.14840(10) 0.0227(5) Uani d 1 . .
    H H5A 0.331597 -0.261481 0.159853 0.027 Uiso calc 1 . .
    H H5B 0.256683 -0.170763 0.107196 0.027 Uiso calc 1 . .
    C C6 0.0888(2) -0.2675(3) 0.15827(9) 0.0235(5) Uani d 1 . .
    H H6A 0.003576 -0.196276 0.148603 0.028 Uiso calc 1 . .
    H H6B 0.080682 -0.293268 0.199174 0.028 Uiso calc 1 . .
    C C7 0.0675(3) -0.4096(3) 0.12246(10) 0.0276(5) Uani d 1 . .
    H H7A -0.043276 -0.441482 0.124454 0.033 Uiso calc 1 . .
    H H7B 0.088694 -0.384982 0.082158 0.033 Uiso calc 1 . .
    C C8 0.1711(3) -0.5404(3) 0.14028(10) 0.0266(5) Uani d 1 . .
    H H8A 0.167251 -0.617074 0.109820 0.032 Uiso calc 1 . .
    H H8B 0.280678 -0.504984 0.144025 0.032 Uiso calc 1 . .
    C C9 0.1242(4) -0.6123(3) 0.19610(10) 0.0419(7) Uani d 1 . .
    H H9A 0.196358 -0.694365 0.205375 0.063 Uiso calc 1 . .
    H H9B 0.017325 -0.651426 0.192311 0.063 Uiso calc 1 . .
    H H9C 0.128656 -0.537412 0.226628 0.063 Uiso calc 1 . .
    C C10 0.7312(2) 0.0792(2) 0.08774(8) 0.0180(4) Uani d 1 . .
    C C11 0.6759(3) -0.0238(3) 0.04790(8) 0.0233(5) Uani d 1 . .
    H H11 0.566983 -0.044721 0.045292 0.028 Uiso calc 1 . .
    C C12 0.7783(3) -0.0967(3) 0.01174(9) 0.0281(5) Uani d 1 . .
    H H12 0.739177 -0.167693 -0.015100 0.034 Uiso calc 1 . .
    C C13 0.9367(3) -0.0659(3) 0.01483(9) 0.0251(5) Uani d 1 . .
    H H13 1.006816 -0.116904 -0.009422 0.030 Uiso calc 1 . .
    C C14 0.9931(3) 0.0395(3) 0.05343(9) 0.0255(5) Uani d 1 . .
    H H14 1.101677 0.062665 0.054982 0.031 Uiso calc 1 . .
    C C15 0.8914(2) 0.1110(3) 0.08962(9) 0.0218(5) Uani d 1 . .
    H H15 0.930918 0.182710 0.116121 0.026 Uiso calc 1 . .
    C C16 0.6343(2) 0.3240(3) 0.13026(9) 0.0183(4) Uani d 1 . .
    C C17 0.6326(3) 0.3966(3) 0.07764(9) 0.0226(5) Uani d 1 . .
    H H17 0.630919 0.339925 0.043366 0.027 Uiso calc 1 . .
    C C18 0.6334(3) 0.5521(3) 0.07531(10) 0.0272(5) Uani d 1 . .
    H H18 0.632310 0.601665 0.039448 0.033 Uiso calc 1 . .
    C C19 0.6356(3) 0.6347(3) 0.12531(10) 0.0270(5) Uani d 1 . .
    H H19 0.637703 0.740892 0.123583 0.032 Uiso calc 1 . .
    C C20 0.6349(3) 0.5640(3) 0.17756(10) 0.0268(5) Uani d 1 . .
    H H20 0.635423 0.621297 0.211695 0.032 Uiso calc 1 . .
    C C21 0.6335(3) 0.4083(3) 0.18019(9) 0.0225(5) Uani d 1 . .
    H H21 0.632013 0.359441 0.216169 0.027 Uiso calc 1 . .
    O O3 0.12971(17) -0.14512(18) 0.42033(6) 0.0215(3) Uani d 1 . .
    O O4 -0.05315(16) 0.08484(18) 0.25818(6) 0.0211(3) Uani d 1 . .
    N N3 0.07408(19) -0.0073(2) 0.33947(7) 0.0174(4) Uani d 1 . .
    N N4 -0.1652(2) -0.0900(2) 0.31728(7) 0.0171(4) Uani d 1 . .
    H H4 -0.251179 -0.108464 0.297218 0.020 Uiso calc 1 . .
    C C22 -0.1303(2) -0.1580(2) 0.37302(8) 0.0156(4) Uani d 1 . .
    C C23 0.0409(2) -0.1062(2) 0.38216(8) 0.0165(4) Uani d 1 . .
    C C24 -0.0520(2) 0.0039(2) 0.30000(8) 0.0159(4) Uani d 1 . .
    C C25 0.2227(2) 0.0740(3) 0.33453(9) 0.0195(4) Uani d 1 . .
    H H25A 0.222194 0.128966 0.297854 0.023 Uiso calc 1 . .
    H H25B 0.309686 0.000876 0.333843 0.023 Uiso calc 1 . .
    C C26 0.2528(2) 0.1844(2) 0.38293(9) 0.0209(4) Uani d 1 . .
    H H26A 0.249605 0.130812 0.419844 0.025 Uiso calc 1 . .
    H H26B 0.168936 0.260940 0.382658 0.025 Uiso calc 1 . .
    C C27 0.4117(3) 0.2616(3) 0.37742(10) 0.0245(5) Uani d 1 . .
    H H27A 0.439694 0.308408 0.414494 0.029 Uiso calc 1 . .
    H H27B 0.491579 0.184291 0.369658 0.029 Uiso calc 1 . .
    C C28 0.4198(3) 0.3809(3) 0.33106(10) 0.0260(5) Uani d 1 . .
    H H28A 0.529321 0.416227 0.328602 0.031 Uiso calc 1 . .
    H H28B 0.390887 0.334628 0.293973 0.031 Uiso calc 1 . .
    C C29 0.3142(3) 0.5154(3) 0.34056(10) 0.0310(5) Uani d 1 . .
    H H29A 0.203536 0.483499 0.336361 0.037 Uiso calc 1 . .
    H H29B 0.330425 0.552037 0.380079 0.037 Uiso calc 1 . .
    C C30 0.3441(3) 0.6422(3) 0.29951(10) 0.0360(6) Uani d 1 . .
    H H30A 0.268833 0.722907 0.306012 0.054 Uiso calc 1 . .
    H H30B 0.332232 0.605846 0.260236 0.054 Uiso calc 1 . .
    H H30C 0.450798 0.680161 0.305678 0.054 Uiso calc 1 . .
    C C31 -0.2355(2) -0.0896(2) 0.41845(8) 0.0153(4) Uani d 1 . .
    C C32 -0.1822(2) 0.0121(3) 0.45902(8) 0.0203(4) Uani d 1 . .
    H H32 -0.074698 0.039296 0.460449 0.024 Uiso calc 1 . .
    C C33 -0.2851(3) 0.0744(3) 0.49763(9) 0.0234(5) Uani d 1 . .
    H H33 -0.247891 0.144943 0.524997 0.028 Uiso calc 1 . .
    C C34 -0.4416(3) 0.0341(3) 0.49632(9) 0.0238(5) Uani d 1 . .
    H H34 -0.511559 0.076359 0.522925 0.029 Uiso calc 1 . .
    C C35 -0.4958(3) -0.0679(2) 0.45615(9) 0.0217(5) Uani d 1 . .
    H H35 -0.603251 -0.095555 0.455181 0.026 Uiso calc 1 . .
    C C36 -0.3939(2) -0.1296(2) 0.41738(9) 0.0190(4) Uani d 1 . .
    H H36 -0.431794 -0.199576 0.389908 0.023 Uiso calc 1 . .
    C C37 -0.1370(2) -0.3279(2) 0.37254(9) 0.0166(4) Uani d 1 . .
    C C38 -0.1427(2) -0.4055(3) 0.42411(9) 0.0210(5) Uani d 1 . .
    H H38 -0.142967 -0.351269 0.458963 0.025 Uiso calc 1 . .
    C C39 -0.1481(3) -0.5607(3) 0.42524(10) 0.0238(5) Uani d 1 . .
    H H39 -0.152122 -0.612256 0.460625 0.029 Uiso calc 1 . .
    C C40 -0.1476(3) -0.6403(3) 0.37429(10) 0.0234(5) Uani d 1 . .
    H H40 -0.153488 -0.746382 0.374750 0.028 Uiso calc 1 . .
    C C41 -0.1384(3) -0.5649(3) 0.32287(10) 0.0228(5) Uani d 1 . .
    H H41 -0.135478 -0.619557 0.288157 0.027 Uiso calc 1 . .
    C C42 -0.1333(2) -0.4091(3) 0.32185(9) 0.0199(5) Uani d 1 . .
    H H42 -0.127420 -0.357978 0.286422 0.024 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
    O1 C2 . 1.213(2) ?
    O2 C3 . 1.223(2) ?
    N1 C2 . 1.366(3) ?
    N1 C3 . 1.408(2) ?
    N1 C4 . 1.466(3) ?
    N2 C3 . 1.342(3) ?
    N2 C1 . 1.464(2) ?
    N2 H2 . 0.8800 ?
    C1 C10 . 1.531(3) ?
    C1 C16 . 1.531(3) ?
    C1 C2 . 1.547(3) ?
    C4 C5 . 1.513(3) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.526(3) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 C7 . 1.531(3) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.520(3) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C9 . 1.518(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 C11 . 1.388(3) ?
    C10 C15 . 1.397(3) ?
    C11 C12 . 1.391(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.381(3) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.387(3) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.382(3) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 C21 . 1.392(3) ?
    C16 C17 . 1.394(3) ?
    C17 C18 . 1.391(3) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.385(3) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.379(3) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.393(4) ?
    C20 H20 . 0.9500 ?
    C21 H21 . 0.9500 ?
    O3 C23 . 1.213(2) ?
    O4 C24 . 1.219(2) ?
    N3 C23 . 1.369(3) ?
    N3 C24 . 1.410(2) ?
    N3 C25 . 1.469(3) ?
    N4 C24 . 1.348(3) ?
    N4 C22 . 1.467(2) ?
    N4 H4 . 0.8800 ?
    C22 C37 . 1.520(3) ?
    C22 C31 . 1.533(3) ?
    C22 C23 . 1.544(3) ?
    C25 C26 . 1.522(3) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C26 C27 . 1.530(3) ?
    C26 H26A . 0.9900 ?
    C26 H26B . 0.9900 ?
    C27 C28 . 1.525(3) ?
    C27 H27A . 0.9900 ?
    C27 H27B . 0.9900 ?
    C28 C29 . 1.522(3) ?
    C28 H28A . 0.9900 ?
    C28 H28B . 0.9900 ?
    C29 C30 . 1.512(3) ?
    C29 H29A . 0.9900 ?
    C29 H29B . 0.9900 ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
    C31 C32 . 1.386(3) ?
    C31 C36 . 1.399(3) ?
    C32 C33 . 1.390(3) ?
    C32 H32 . 0.9500 ?
    C33 C34 . 1.383(3) ?
    C33 H33 . 0.9500 ?
    C34 C35 . 1.384(3) ?
    C34 H34 . 0.9500 ?
    C35 C36 . 1.385(3) ?
    C35 H35 . 0.9500 ?
    C36 H36 . 0.9500 ?
    C37 C42 . 1.393(3) ?
    C37 C38 . 1.395(3) ?
    C38 C39 . 1.388(3) ?
    C38 H38 . 0.9500 ?
    C39 C40 . 1.390(3) ?
    C39 H39 . 0.9500 ?
    C40 C41 . 1.385(3) ?
    C40 H40 . 0.9500 ?
    C41 C42 . 1.393(3) ?
    C41 H41 . 0.9500 ?
    C42 H42 . 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
    C2 N1 C3 . . 111.46(16) ?
    C2 N1 C4 . . 124.74(16) ?
    C3 N1 C4 . . 123.75(17) ?
    C3 N2 C1 . . 113.56(16) ?
    C3 N2 H2 . . 123.2 ?
    C1 N2 H2 . . 123.2 ?
    N2 C1 C10 . . 109.88(17) ?
    N2 C1 C16 . . 113.07(17) ?
    C10 C1 C16 . . 112.73(18) ?
    N2 C1 C2 . . 100.15(16) ?
    C10 C1 C2 . . 111.81(17) ?
    C16 C1 C2 . . 108.54(18) ?
    O1 C2 N1 . . 126.36(19) ?
    O1 C2 C1 . . 126.3(2) ?
    N1 C2 C1 . . 107.32(16) ?
    O2 C3 N2 . . 128.42(19) ?
    O2 C3 N1 . . 124.22(19) ?
    N2 C3 N1 . . 107.36(17) ?
    N1 C4 C5 . . 112.31(17) ?
    N1 C4 H4A . . 109.1 ?
    C5 C4 H4A . . 109.1 ?
    N1 C4 H4B . . 109.1 ?
    C5 C4 H4B . . 109.1 ?
    H4A C4 H4B . . 107.9 ?
    C4 C5 C6 . . 112.39(18) ?
    C4 C5 H5A . . 109.1 ?
    C6 C5 H5A . . 109.1 ?
    C4 C5 H5B . . 109.1 ?
    C6 C5 H5B . . 109.1 ?
    H5A C5 H5B . . 107.9 ?
    C5 C6 C7 . . 112.30(18) ?
    C5 C6 H6A . . 109.1 ?
    C7 C6 H6A . . 109.1 ?
    C5 C6 H6B . . 109.1 ?
    C7 C6 H6B . . 109.1 ?
    H6A C6 H6B . . 107.9 ?
    C8 C7 C6 . . 115.12(18) ?
    C8 C7 H7A . . 108.5 ?
    C6 C7 H7A . . 108.5 ?
    C8 C7 H7B . . 108.5 ?
    C6 C7 H7B . . 108.5 ?
    H7A C7 H7B . . 107.5 ?
    C9 C8 C7 . . 113.6(2) ?
    C9 C8 H8A . . 108.8 ?
    C7 C8 H8A . . 108.8 ?
    C9 C8 H8B . . 108.8 ?
    C7 C8 H8B . . 108.8 ?
    H8A C8 H8B . . 107.7 ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C11 C10 C15 . . 118.4(2) ?
    C11 C10 C1 . . 123.27(19) ?
    C15 C10 C1 . . 118.18(19) ?
    C10 C11 C12 . . 120.8(2) ?
    C10 C11 H11 . . 119.6 ?
    C12 C11 H11 . . 119.6 ?
    C13 C12 C11 . . 120.0(2) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C12 C13 C14 . . 119.8(2) ?
    C12 C13 H13 . . 120.1 ?
    C14 C13 H13 . . 120.1 ?
    C15 C14 C13 . . 120.0(2) ?
    C15 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C14 C15 C10 . . 120.8(2) ?
    C14 C15 H15 . . 119.6 ?
    C10 C15 H15 . . 119.6 ?
    C21 C16 C17 . . 119.5(2) ?
    C21 C16 C1 . . 121.0(2) ?
    C17 C16 C1 . . 119.4(2) ?
    C18 C17 C16 . . 120.0(2) ?
    C18 C17 H17 . . 120.0 ?
    C16 C17 H17 . . 120.0 ?
    C19 C18 C17 . . 119.9(2) ?
    C19 C18 H18 . . 120.0 ?
    C17 C18 H18 . . 120.0 ?
    C20 C19 C18 . . 120.5(2) ?
    C20 C19 H19 . . 119.8 ?
    C18 C19 H19 . . 119.8 ?
    C19 C20 C21 . . 119.8(2) ?
    C19 C20 H20 . . 120.1 ?
    C21 C20 H20 . . 120.1 ?
    C16 C21 C20 . . 120.2(2) ?
    C16 C21 H21 . . 119.9 ?
    C20 C21 H21 . . 119.9 ?
    C23 N3 C24 . . 111.06(16) ?
    C23 N3 C25 . . 124.62(16) ?
    C24 N3 C25 . . 124.30(17) ?
    C24 N4 C22 . . 112.97(16) ?
    C24 N4 H4 . . 123.5 ?
    C22 N4 H4 . . 123.5 ?
    N4 C22 C37 . . 113.61(17) ?
    N4 C22 C31 . . 109.97(16) ?
    C37 C22 C31 . . 112.37(17) ?
    N4 C22 C23 . . 100.14(16) ?
    C37 C22 C23 . . 109.62(17) ?
    C31 C22 C23 . . 110.48(17) ?
    O3 C23 N3 . . 126.09(19) ?
    O3 C23 C22 . . 126.43(19) ?
    N3 C23 C22 . . 107.47(16) ?
    O4 C24 N4 . . 128.04(18) ?
    O4 C24 N3 . . 124.38(19) ?
    N4 C24 N3 . . 107.58(17) ?
    N3 C25 C26 . . 113.33(17) ?
    N3 C25 H25A . . 108.9 ?
    C26 C25 H25A . . 108.9 ?
    N3 C25 H25B . . 108.9 ?
    C26 C25 H25B . . 108.9 ?
    H25A C25 H25B . . 107.7 ?
    C25 C26 C27 . . 111.52(18) ?
    C25 C26 H26A . . 109.3 ?
    C27 C26 H26A . . 109.3 ?
    C25 C26 H26B . . 109.3 ?
    C27 C26 H26B . . 109.3 ?
    H26A C26 H26B . . 108.0 ?
    C28 C27 C26 . . 115.30(18) ?
    C28 C27 H27A . . 108.4 ?
    C26 C27 H27A . . 108.5 ?
    C28 C27 H27B . . 108.5 ?
    C26 C27 H27B . . 108.4 ?
    H27A C27 H27B . . 107.5 ?
    C29 C28 C27 . . 114.42(19) ?
    C29 C28 H28A . . 108.7 ?
    C27 C28 H28A . . 108.7 ?
    C29 C28 H28B . . 108.7 ?
    C27 C28 H28B . . 108.7 ?
    H28A C28 H28B . . 107.6 ?
    C30 C29 C28 . . 113.0(2) ?
    C30 C29 H29A . . 109.0 ?
    C28 C29 H29A . . 109.0 ?
    C30 C29 H29B . . 109.0 ?
    C28 C29 H29B . . 109.0 ?
    H29A C29 H29B . . 107.8 ?
    C29 C30 H30A . . 109.5 ?
    C29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    C32 C31 C36 . . 118.98(19) ?
    C32 C31 C22 . . 123.29(18) ?
    C36 C31 C22 . . 117.71(18) ?
    C31 C32 C33 . . 120.4(2) ?
    C31 C32 H32 . . 119.8 ?
    C33 C32 H32 . . 119.8 ?
    C34 C33 C32 . . 120.2(2) ?
    C34 C33 H33 . . 119.9 ?
    C32 C33 H33 . . 119.9 ?
    C33 C34 C35 . . 119.8(2) ?
    C33 C34 H34 . . 120.1 ?
    C35 C34 H34 . . 120.1 ?
    C34 C35 C36 . . 120.2(2) ?
    C34 C35 H35 . . 119.9 ?
    C36 C35 H35 . . 119.9 ?
    C35 C36 C31 . . 120.4(2) ?
    C35 C36 H36 . . 119.8 ?
    C31 C36 H36 . . 119.8 ?
    C42 C37 C38 . . 118.8(2) ?
    C42 C37 C22 . . 121.68(19) ?
    C38 C37 C22 . . 119.48(19) ?
    C39 C38 C37 . . 121.0(2) ?
    C39 C38 H38 . . 119.5 ?
    C37 C38 H38 . . 119.5 ?
    C38 C39 C40 . . 119.6(2) ?
    C38 C39 H39 . . 120.2 ?
    C40 C39 H39 . . 120.2 ?
    C41 C40 C39 . . 120.0(2) ?
    C41 C40 H40 . . 120.0 ?
    C39 C40 H40 . . 120.0 ?
    C40 C41 C42 . . 120.2(2) ?
    C40 C41 H41 . . 119.9 ?
    C42 C41 H41 . . 119.9 ?
    C41 C42 C37 . . 120.3(2) ?
    C41 C42 H42 . . 119.8 ?
    C37 C42 H42 . . 119.8 ?
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
    C3 N2 C1 C10 . . . . -114.0(2) ?
    C3 N2 C1 C16 . . . . 119.1(2) ?
    C3 N2 C1 C2 . . . . 3.8(2) ?
    C3 N1 C2 O1 . . . . -179.8(2) ?
    C4 N1 C2 O1 . . . . 2.7(4) ?
    C3 N1 C2 C1 . . . . -0.1(2) ?
    C4 N1 C2 C1 . . . . -177.53(19) ?
    N2 C1 C2 O1 . . . . 177.7(2) ?
    C10 C1 C2 O1 . . . . -66.0(3) ?
    C16 C1 C2 O1 . . . . 59.0(3) ?
    N2 C1 C2 N1 . . . . -2.1(2) ?
    C10 C1 C2 N1 . . . . 114.28(19) ?
    C16 C1 C2 N1 . . . . -120.8(2) ?
    C1 N2 C3 O2 . . . . 176.6(2) ?
    C1 N2 C3 N1 . . . . -4.0(3) ?
    C2 N1 C3 O2 . . . . -178.2(2) ?
    C4 N1 C3 O2 . . . . -0.7(3) ?
    C2 N1 C3 N2 . . . . 2.5(3) ?
    C4 N1 C3 N2 . . . . 179.94(19) ?
    C2 N1 C4 C5 . . . . 77.6(3) ?
    C3 N1 C4 C5 . . . . -99.6(2) ?
    N1 C4 C5 C6 . . . . 179.51(17) ?
    C4 C5 C6 C7 . . . . 177.25(18) ?
    C5 C6 C7 C8 . . . . 69.8(3) ?
    C6 C7 C8 C9 . . . . 71.7(3) ?
    N2 C1 C10 C11 . . . . 107.6(2) ?
    C16 C1 C10 C11 . . . . -125.3(2) ?
    C2 C1 C10 C11 . . . . -2.6(3) ?
    N2 C1 C10 C15 . . . . -68.7(2) ?
    C16 C1 C10 C15 . . . . 58.4(2) ?
    C2 C1 C10 C15 . . . . -178.94(18) ?
    C15 C10 C11 C12 . . . . 1.7(3) ?
    C1 C10 C11 C12 . . . . -174.5(2) ?
    C10 C11 C12 C13 . . . . -0.6(3) ?
    C11 C12 C13 C14 . . . . -1.0(4) ?
    C12 C13 C14 C15 . . . . 1.5(3) ?
    C13 C14 C15 C10 . . . . -0.4(3) ?
    C11 C10 C15 C14 . . . . -1.2(3) ?
    C1 C10 C15 C14 . . . . 175.2(2) ?
    N2 C1 C16 C21 . . . . -16.0(3) ?
    C10 C1 C16 C21 . . . . -141.4(2) ?
    C2 C1 C16 C21 . . . . 94.2(2) ?
    N2 C1 C16 C17 . . . . 167.80(18) ?
    C10 C1 C16 C17 . . . . 42.4(3) ?
    C2 C1 C16 C17 . . . . -82.0(2) ?
    C21 C16 C17 C18 . . . . 1.3(3) ?
    C1 C16 C17 C18 . . . . 177.6(2) ?
    C16 C17 C18 C19 . . . . -0.1(4) ?
    C17 C18 C19 C20 . . . . -0.9(4) ?
    C18 C19 C20 C21 . . . . 0.7(4) ?
    C17 C16 C21 C20 . . . . -1.6(3) ?
    C1 C16 C21 C20 . . . . -177.8(2) ?
    C19 C20 C21 C16 . . . . 0.6(4) ?
    C24 N4 C22 C37 . . . . -125.53(19) ?
    C24 N4 C22 C31 . . . . 107.5(2) ?
    C24 N4 C22 C23 . . . . -8.8(2) ?
    C24 N3 C23 O3 . . . . 175.7(2) ?
    C25 N3 C23 O3 . . . . -3.0(3) ?
    C24 N3 C23 C22 . . . . -4.8(2) ?
    C25 N3 C23 C22 . . . . 176.59(18) ?
    N4 C22 C23 O3 . . . . -172.6(2) ?
    C37 C22 C23 O3 . . . . -52.9(3) ?
    C31 C22 C23 O3 . . . . 71.5(3) ?
    N4 C22 C23 N3 . . . . 7.8(2) ?
    C37 C22 C23 N3 . . . . 127.54(18) ?
    C31 C22 C23 N3 . . . . -108.09(18) ?
    C22 N4 C24 O4 . . . . -173.8(2) ?
    C22 N4 C24 N3 . . . . 6.5(2) ?
    C23 N3 C24 O4 . . . . 179.5(2) ?
    C25 N3 C24 O4 . . . . -1.9(3) ?
    C23 N3 C24 N4 . . . . -0.8(2) ?
    C25 N3 C24 N4 . . . . 177.87(18) ?
    C23 N3 C25 C26 . . . . -65.2(3) ?
    C24 N3 C25 C26 . . . . 116.3(2) ?
    N3 C25 C26 C27 . . . . 177.58(17) ?
    C25 C26 C27 C28 . . . . 74.5(2) ?
    C26 C27 C28 C29 . . . . 63.9(3) ?
    C27 C28 C29 C30 . . . . 170.5(2) ?
    N4 C22 C31 C32 . . . . -105.6(2) ?
    C37 C22 C31 C32 . . . . 126.8(2) ?
    C23 C22 C31 C32 . . . . 4.0(3) ?
    N4 C22 C31 C36 . . . . 72.5(2) ?
    C37 C22 C31 C36 . . . . -55.1(2) ?
    C23 C22 C31 C36 . . . . -177.84(18) ?
    C36 C31 C32 C33 . . . . -0.7(3) ?
    C22 C31 C32 C33 . . . . 177.4(2) ?
    C31 C32 C33 C34 . . . . 0.8(3) ?
    C32 C33 C34 C35 . . . . -0.4(3) ?
    C33 C34 C35 C36 . . . . 0.1(3) ?
    C34 C35 C36 C31 . . . . 0.0(3) ?
    C32 C31 C36 C35 . . . . 0.3(3) ?
    C22 C31 C36 C35 . . . . -177.90(18) ?
    N4 C22 C37 C42 . . . . 16.6(3) ?
    C31 C22 C37 C42 . . . . 142.31(19) ?
    C23 C22 C37 C42 . . . . -94.4(2) ?
    N4 C22 C37 C38 . . . . -165.08(18) ?
    C31 C22 C37 C38 . . . . -39.4(3) ?
    C23 C22 C37 C38 . . . . 83.8(2) ?
    C42 C37 C38 C39 . . . . -1.3(3) ?
    C22 C37 C38 C39 . . . . -179.7(2) ?
    C37 C38 C39 C40 . . . . 0.1(4) ?
    C38 C39 C40 C41 . . . . 1.4(4) ?
    C39 C40 C41 C42 . . . . -1.5(4) ?
    C40 C41 C42 C37 . . . . 0.2(4) ?
    C38 C37 C42 C41 . . . . 1.2(3) ?
    C22 C37 C42 C41 . . . . 179.5(2) ?
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
    N2 H2 O4 1_655 0.88 2.04 2.896(2) 165
    N4 H4 O2 1_455 0.88 2.05 2.875(2) 156
    C14 H14 O1 1_655 0.95 2.44 3.370(3) 165
    C33 H33 O3 2_556 0.95 2.48 3.413(3) 169
    C35 H35 O3 1_455 0.95 2.45 3.363(3) 161
    C7 H7A Cg3 1_445 0.99 2.85 3.835(3) 177
