##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-06-08
_journal_date_accepted     2006-06-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      7
_journal_page_first     o2938
_journal_page_last     o2940
_journal_paper_category     EO
_journal_coeditor_code     KJ2015
_publ_contact_author_name     'Castillo, Ivan'
_publ_contact_author_address
;     Instituto de Química
      Universidad Nacional Autónoma de México
      Circuito Exterior, CU
      México, D. F. 04510
      Mexico
;
_publ_contact_author_email     joseivan@servidor.unam.mx
_publ_contact_author_fax     '+(5255) 56162217'
_publ_contact_author_phone     '+(5255) 56224449'
_publ_section_title
;
1,4-Bis(8-tert-butyl-6-methyl-4H-1,3-benzoxazin-3-yl)benzene
;
loop_
    _publ_author_name
    _publ_author_address
    "Huerta, Raúl"
;     Instituto de Química
      Universidad Nacional Autónoma de México
      Circuito Exterior, CU
      México, DF 04510
      Mexico
;
    "Toscano, Rubén A."
;     Instituto de Química
      Universidad Nacional Autónoma de México
      Circuito Exterior, CU
      México, DF 04510
      Mexico
;
    "Castillo, Ivan"
;     Instituto de Química
      Universidad Nacional Autónoma de México
      Circuito Exterior, CU
      México, DF 04510
      Mexico
;
data_I
_chemical_name_systematic
;
1,4-Bis(8-tert-butyl-6-methyl-4H-1,3-benzoxazin-3-yl)benzene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C32 H40 N2 O2'
_chemical_formula_sum     'C32 H40 N2 O2'
_chemical_formula_iupac     'C32 H40 N2 O2'
_chemical_formula_weight     484.66
_chemical_melting_point        .424E-305
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.2670(10)
_cell_length_b     15.443(2)
_cell_length_c     17.913(2)
_cell_angle_alpha     90.00
_cell_angle_beta     92.098(2)
_cell_angle_gamma     90.00
_cell_volume     2838.3(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5532
_cell_measurement_theta_min     2.28
_cell_measurement_theta_max     24.60
_cell_measurement_temperature     294(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.254
_exptl_crystal_size_mid     0.228
_exptl_crystal_size_min     0.122
_exptl_crystal_density_diffrn     1.134
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1048
_exptl_absorpt_coefficient_mu     0.070
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.965
_exptl_absorpt_correction_T_max     0.996
_exptl_special_details
;
¹H NMR (300 MHz, CDCl₃): δ 7.04 (s, 4H, phenylene CH), 6.89
(s, 2H, aromatic CH), 6.63 (s, 2H, aromatic CH), 5.25 (s, 4H,
N--CH₂--O), 4.51 (s, 4H, N---CH₂---C), 2.22 (s, 6H, CH₃),
1.34 (s, 18H, C(CH₃)₃); FAB MS: m/z 484 (M⁺, 98%).
IR (KBr, ν, cm⁻¹) 3421, 3040, 2998, 2958, 2910, 2863, 1742, 1608, 1571,
1513, 1476, 1445, 1387, 1362, 1322, 1252, 1222, 1176, 1133, 1098, 948,
939, 919, 856, 836, 750, 659, 610, 562, 522;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     0.661
_diffrn_reflns_number     21975
_diffrn_reflns_av_R_equivalents     0.0622
_diffrn_reflns_av_sigmaI/netI     0.0569
_diffrn_reflns_theta_min     1.74
_diffrn_reflns_theta_max     25.35
_diffrn_reflns_theta_full     25.35
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     5180
_reflns_number_gt     3379
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1007
_refine_ls_R_factor_gt     0.0616
_refine_ls_wR_factor_gt     0.1424
_refine_ls_wR_factor_ref     0.1595
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     5180
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0696P)²+0.5199P] 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     0.176
_refine_diff_density_min     -0.162
_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'
    '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     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material     SHELXTL
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.6625(2) 0.41329(15) -0.00776(13) 0.0482(6) Uani d . 1 . .
    C C2 0.6983(3) 0.40315(17) -0.08103(14) 0.0641(7) Uani d . 1 . .
    H H2 0.6655 0.3565 -0.1087 0.077 Uiso calc R 1 . .
    C C3 0.7809(3) 0.46027(17) -0.11361(16) 0.0695(8) Uani d . 1 . .
    H H3 0.8042 0.4509 -0.1626 0.083 Uiso calc R 1 . .
    C C4 0.8306(2) 0.53166(16) -0.07542(15) 0.0569(7) Uani d . 1 . .
    C C5 0.7945(2) 0.54223(16) -0.00240(15) 0.0582(7) Uani d . 1 . .
    H H5 0.8255 0.5896 0.0249 0.070 Uiso calc R 1 . .
    C C6 0.7126(2) 0.48312(16) 0.03095(14) 0.0559(6) Uani d . 1 . .
    H H6 0.6913 0.4911 0.0805 0.067 Uiso calc R 1 . .
    O O7 0.59445(15) 0.37658(10) 0.15518(9) 0.0533(4) Uani d . 1 . .
    C C8 0.5102(2) 0.37703(18) 0.08829(14) 0.0617(7) Uani d . 1 . .
    H H8A 0.4383 0.3375 0.0955 0.074 Uiso calc R 1 . .
    H H8B 0.4739 0.4346 0.0816 0.074 Uiso calc R 1 . .
    N N9 0.57328(19) 0.35311(14) 0.02219(11) 0.0563(6) Uani d . 1 . .
    C C10 0.6188(3) 0.26361(16) 0.02997(13) 0.0614(7) Uani d . 1 . .
    H H10A 0.6751 0.2499 -0.0107 0.074 Uiso calc R 1 . .
    H H10B 0.5445 0.2248 0.0267 0.074 Uiso calc R 1 . .
    C C11 0.7772(2) 0.18056(15) 0.11305(14) 0.0556(7) Uani d . 1 . .
    H H11 0.7858 0.1412 0.0742 0.067 Uiso calc R 1 . .
    C C12 0.8498(2) 0.16847(15) 0.17873(14) 0.0546(6) Uani d . 1 . .
    C C13 0.8349(2) 0.22912(15) 0.23478(13) 0.0498(6) Uani d . 1 . .
    H H13 0.8839 0.2220 0.2791 0.060 Uiso calc R 1 . .
    C C14 0.7519(2) 0.29970(14) 0.22915(12) 0.0423(5) Uani d . 1 . .
    C C15 0.6782(2) 0.30746(14) 0.16179(12) 0.0423(5) Uani d . 1 . .
    C C16 0.6922(2) 0.24957(14) 0.10343(12) 0.0458(6) Uani d . 1 . .
    C C17 0.9459(3) 0.09546(18) 0.18823(18) 0.0839(9) Uani d . 1 . .
    H H17A 0.9005 0.0412 0.1850 0.126 Uiso calc R 1 . .
    H H17B 0.9904 0.1002 0.2361 0.126 Uiso calc R 1 . .
    H H17C 1.0081 0.0985 0.1496 0.126 Uiso calc R 1 . .
    C C18 0.7437(2) 0.36676(15) 0.29172(13) 0.0536(6) Uani d . 1 . .
    C C19 0.7824(3) 0.45603(17) 0.26273(17) 0.0738(8) Uani d . 1 . .
    H H19A 0.8667 0.4526 0.2415 0.111 Uiso calc R 1 . .
    H H19B 0.7852 0.4967 0.3033 0.111 Uiso calc R 1 . .
    H H19C 0.7194 0.4748 0.2252 0.111 Uiso calc R 1 . .
    C C20 0.6057(3) 0.37000(19) 0.32141(15) 0.0693(8) Uani d . 1 . .
    H H20A 0.5449 0.3848 0.2815 0.104 Uiso calc R 1 . .
    H H20B 0.6021 0.4128 0.3601 0.104 Uiso calc R 1 . .
    H H20C 0.5836 0.3144 0.3413 0.104 Uiso calc R 1 . .
    C C21 0.8366(3) 0.3447(2) 0.35820(16) 0.0861(10) Uani d . 1 . .
    H H21A 0.8152 0.2886 0.3773 0.129 Uiso calc R 1 . .
    H H21B 0.8278 0.3873 0.3967 0.129 Uiso calc R 1 . .
    H H21C 0.9247 0.3444 0.3421 0.129 Uiso calc R 1 . .
    O O22 0.90470(15) 0.72024(11) -0.03936(10) 0.0609(5) Uani d . 1 . .
    C C23 0.9857(3) 0.65030(18) -0.0664(2) 0.0763(9) Uani d . 1 . .
    H H23A 1.0549 0.6752 -0.0950 0.092 Uiso calc R 1 . .
    H H23B 1.0260 0.6207 -0.0238 0.092 Uiso calc R 1 . .
    N N24 0.9178(2) 0.58853(14) -0.11160(14) 0.0693(6) Uani d . 1 . .
    C C25 0.8657(3) 0.63163(18) -0.17882(16) 0.0772(9) Uani d . 1 . .
    H H25A 0.8070 0.5926 -0.2059 0.093 Uiso calc R 1 . .
    H H25B 0.9367 0.6456 -0.2110 0.093 Uiso calc R 1 . .
    C C26 0.7030(3) 0.74920(18) -0.21014(14) 0.0643(7) Uani d . 1 . .
    H H26 0.6908 0.7240 -0.2570 0.077 Uiso calc R 1 . .
    C C27 0.6306(3) 0.82064(17) -0.19300(14) 0.0602(7) Uani d . 1 . .
    C C28 0.6500(2) 0.85536(15) -0.12190(13) 0.0522(6) Uani d . 1 . .
    H H28 0.6000 0.9030 -0.1091 0.063 Uiso calc R 1 . .
    C C29 0.7394(2) 0.82343(14) -0.06882(12) 0.0438(5) Uani d . 1 . .
    C C30 0.8132(2) 0.75184(15) -0.09020(13) 0.0478(6) Uani d . 1 . .
    C C31 0.7940(2) 0.71313(16) -0.15998(14) 0.0554(6) Uani d . 1 . .
    C C32 0.5316(3) 0.8596(2) -0.24780(17) 0.0910(11) Uani d . 1 . .
    H H32A 0.5582 0.8494 -0.2979 0.137 Uiso calc R 1 . .
    H H32B 0.5256 0.9208 -0.2392 0.137 Uiso calc R 1 . .
    H H32C 0.4481 0.8334 -0.2411 0.137 Uiso calc R 1 . .
    C C33 0.7567(2) 0.86609(16) 0.00844(13) 0.0532(6) Uani d . 1 . .
    C C34 0.8933(3) 0.9063(2) 0.01510(17) 0.0778(9) Uani d . 1 . .
    H H34A 0.9006 0.9512 -0.0215 0.117 Uiso calc R 1 . .
    H H34B 0.9574 0.8624 0.0068 0.117 Uiso calc R 1 . .
    H H34C 0.9073 0.9303 0.0642 0.117 Uiso calc R 1 . .
    C C35 0.6578(3) 0.93859(19) 0.01977(16) 0.0782(8) Uani d . 1 . .
    H H35A 0.6700 0.9833 -0.0166 0.117 Uiso calc R 1 . .
    H H35B 0.6704 0.9622 0.0691 0.117 Uiso calc R 1 . .
    H H35C 0.5711 0.9157 0.0139 0.117 Uiso calc R 1 . .
    C C36 0.7376(3) 0.7997(2) 0.07079(15) 0.0802(9) Uani d . 1 . .
    H H36A 0.7455 0.8280 0.1184 0.120 Uiso calc R 1 . .
    H H36B 0.8028 0.7553 0.0681 0.120 Uiso calc R 1 . .
    H H36C 0.6527 0.7741 0.0648 0.120 Uiso calc R 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
    C1 C6 . 1.372(3) ?
    C1 C2 . 1.385(3) ?
    C1 N9 . 1.424(3) yes
    C2 C3 . 1.369(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.385(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.382(3) ?
    C4 N24 . 1.427(3) yes
    C5 C6 . 1.391(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    O7 C15 . 1.373(3) yes
    O7 C8 . 1.452(3) yes
    C8 N9 . 1.419(3) yes
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    N9 C10 . 1.464(3) yes
    C10 C16 . 1.508(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.382(3) ?
    C11 C16 . 1.385(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.386(3) ?
    C12 C17 . 1.504(3) ?
    C13 C14 . 1.385(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.406(3) ?
    C14 C18 . 1.531(3) ?
    C15 C16 . 1.387(3) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 C19 . 1.531(4) ?
    C18 C20 . 1.533(3) ?
    C18 C21 . 1.536(4) ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    O22 C30 . 1.374(3) yes
    O22 C23 . 1.457(3) yes
    C23 N24 . 1.417(4) yes
    C23 H23A . 0.9700 ?
    C23 H23B . 0.9700 ?
    N24 C25 . 1.460(4) yes
    C25 C31 . 1.503(4) ?
    C25 H25A . 0.9700 ?
    C25 H25B . 0.9700 ?
    C26 C27 . 1.372(4) ?
    C26 C31 . 1.389(3) ?
    C26 H26 . 0.9300 ?
    C27 C28 . 1.389(3) ?
    C27 C32 . 1.512(4) ?
    C28 C29 . 1.388(3) ?
    C28 H28 . 0.9300 ?
    C29 C30 . 1.402(3) ?
    C29 C33 . 1.537(3) ?
    C30 C31 . 1.393(3) ?
    C32 H32A . 0.9600 ?
    C32 H32B . 0.9600 ?
    C32 H32C . 0.9600 ?
    C33 C35 . 1.530(4) ?
    C33 C36 . 1.534(3) ?
    C33 C34 . 1.534(3) ?
    C34 H34A . 0.9600 ?
    C34 H34B . 0.9600 ?
    C34 H34C . 0.9600 ?
    C35 H35A . 0.9600 ?
    C35 H35B . 0.9600 ?
    C35 H35C . 0.9600 ?
    C36 H36A . 0.9600 ?
    C36 H36B . 0.9600 ?
    C36 H36C . 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
    C6 C1 C2 . . 117.4(2) ?
    C6 C1 N9 . . 123.8(2) ?
    C2 C1 N9 . . 118.7(2) ?
    C3 C2 C1 . . 121.4(2) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    C2 C3 C4 . . 121.7(2) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C5 C4 C3 . . 117.0(2) ?
    C5 C4 N24 . . 123.5(2) ?
    C3 C4 N24 . . 119.5(2) ?
    C4 C5 C6 . . 121.1(2) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C1 C6 C5 . . 121.3(2) ?
    C1 C6 H6 . . 119.3 ?
    C5 C6 H6 . . 119.3 ?
    C15 O7 C8 . . 115.29(18) yes
    N9 C8 O7 . . 114.25(19) yes
    N9 C8 H8A . . 108.7 ?
    O7 C8 H8A . . 108.7 ?
    N9 C8 H8B . . 108.7 ?
    O7 C8 H8B . . 108.7 ?
    H8A C8 H8B . . 107.6 ?
    C8 N9 C1 . . 117.7(2) yes
    C8 N9 C10 . . 108.66(19) yes
    C1 N9 C10 . . 116.4(2) yes
    N9 C10 C16 . . 111.5(2) yes
    N9 C10 H10A . . 109.3 ?
    C16 C10 H10A . . 109.3 ?
    N9 C10 H10B . . 109.3 ?
    C16 C10 H10B . . 109.3 ?
    H10A C10 H10B . . 108.0 ?
    C12 C11 C16 . . 121.9(2) ?
    C12 C11 H11 . . 119.1 ?
    C16 C11 H11 . . 119.1 ?
    C11 C12 C13 . . 117.1(2) ?
    C11 C12 C17 . . 121.9(2) ?
    C13 C12 C17 . . 120.9(2) ?
    C14 C13 C12 . . 124.3(2) ?
    C14 C13 H13 . . 117.9 ?
    C12 C13 H13 . . 117.9 ?
    C13 C14 C15 . . 116.1(2) ?
    C13 C14 C18 . . 122.0(2) ?
    C15 C14 C18 . . 121.9(2) ?
    O7 C15 C16 . . 121.2(2) ?
    O7 C15 C14 . . 117.14(19) ?
    C16 C15 C14 . . 121.6(2) ?
    C11 C16 C15 . . 119.0(2) ?
    C11 C16 C10 . . 120.8(2) ?
    C15 C16 C10 . . 120.2(2) ?
    C12 C17 H17A . . 109.5 ?
    C12 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C12 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C14 C18 C19 . . 109.8(2) ?
    C14 C18 C20 . . 110.64(19) ?
    C19 C18 C20 . . 110.0(2) ?
    C14 C18 C21 . . 111.6(2) ?
    C19 C18 C21 . . 107.6(2) ?
    C20 C18 C21 . . 107.1(2) ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C18 C20 H20A . . 109.5 ?
    C18 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C18 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C18 C21 H21A . . 109.5 ?
    C18 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C18 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C30 O22 C23 . . 115.3(2) yes
    N24 C23 O22 . . 114.5(2) yes
    N24 C23 H23A . . 108.6 ?
    O22 C23 H23A . . 108.6 ?
    N24 C23 H23B . . 108.6 ?
    O22 C23 H23B . . 108.6 ?
    H23A C23 H23B . . 107.6 ?
    C23 N24 C4 . . 117.3(2) yes
    C23 N24 C25 . . 108.8(2) yes
    C4 N24 C25 . . 116.0(2) yes
    N24 C25 C31 . . 111.4(2) yes
    N24 C25 H25A . . 109.4 ?
    C31 C25 H25A . . 109.4 ?
    N24 C25 H25B . . 109.4 ?
    C31 C25 H25B . . 109.4 ?
    H25A C25 H25B . . 108.0 ?
    C27 C26 C31 . . 122.4(2) ?
    C27 C26 H26 . . 118.8 ?
    C31 C26 H26 . . 118.8 ?
    C26 C27 C28 . . 117.0(2) ?
    C26 C27 C32 . . 122.2(3) ?
    C28 C27 C32 . . 120.8(3) ?
    C29 C28 C27 . . 124.1(2) ?
    C29 C28 H28 . . 118.0 ?
    C27 C28 H28 . . 118.0 ?
    C28 C29 C30 . . 116.3(2) ?
    C28 C29 C33 . . 121.1(2) ?
    C30 C29 C33 . . 122.6(2) ?
    O22 C30 C31 . . 120.9(2) ?
    O22 C30 C29 . . 117.6(2) ?
    C31 C30 C29 . . 121.6(2) ?
    C26 C31 C30 . . 118.6(2) ?
    C26 C31 C25 . . 120.9(2) ?
    C30 C31 C25 . . 120.4(2) ?
    C27 C32 H32A . . 109.5 ?
    C27 C32 H32B . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    C27 C32 H32C . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 109.5 ?
    C35 C33 C36 . . 106.9(2) ?
    C35 C33 C34 . . 107.6(2) ?
    C36 C33 C34 . . 110.7(2) ?
    C35 C33 C29 . . 112.2(2) ?
    C36 C33 C29 . . 110.8(2) ?
    C34 C33 C29 . . 108.6(2) ?
    C33 C34 H34A . . 109.5 ?
    C33 C34 H34B . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    C33 C34 H34C . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
    C33 C35 H35A . . 109.5 ?
    C33 C35 H35B . . 109.5 ?
    H35A C35 H35B . . 109.5 ?
    C33 C35 H35C . . 109.5 ?
    H35A C35 H35C . . 109.5 ?
    H35B C35 H35C . . 109.5 ?
    C33 C36 H36A . . 109.5 ?
    C33 C36 H36B . . 109.5 ?
    H36A C36 H36B . . 109.5 ?
    C33 C36 H36C . . 109.5 ?
    H36A C36 H36C . . 109.5 ?
    H36B C36 H36C . . 109.5 ?
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
    C8 H8A Cg3 3_665 0.97 2.66 3.608(3) 166 yes
    C8 H8B Cg1 3_665 0.97 2.75 3.592(3) 145 yes
    C23 H23A Cg2 3_765 0.97 2.68 3.650(3) 174 yes
    C23 H23B Cg1 3_765 0.97 2.95 3.807(3) 148 yes
    C32 H32C Cg2 3_665 0.96 2.80 3.712(3) 160 no
