##############################################################################
#                                                                            #
# 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 v2015.9-0'
_journal_date_recd_electronic     2016-12-12
_journal_date_accepted     2016-12-14
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue     12
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S241431461601988X
_journal_coeditor_code     VM4019
_publ_contact_author_name     'Essaghouani, Abdelhanine'
_publ_contact_author_address
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
_publ_contact_author_email     essaghouani.hanine@gmail.com
_publ_contact_author_fax     ?
_publ_contact_author_phone      212670503002
_publ_section_title
;
1-Benzyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Essaghouani, Abdelhanine' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Boulhaoua, Mohammed' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Lahmidi, Sanae' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'El Hafi, Mohamed' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Essassi, El Mokhtar' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Mague, Joel T.' .
;
Department of Chemistry
Tulane University
New Orleans, LA 70118
USA
;
_publ_section_synopsis
;
In the title molecule, the seven-membered ring adopts a boat conformation.
Pairwise C---H...π(ring) interactions form centrosymmetric dimers which pack
in zigzag layers associated through weak C---H...O hydrogen bonds.
;
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
1-Benzyl-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H18 N2 O'
_chemical_formula_sum     'C22 H18 N2 O'
_chemical_formula_iupac     'C22 H18 N2 O'
_chemical_formula_weight     326.38
_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/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.6973(7)
_cell_length_b     5.9179(3)
_cell_length_c     19.8537(9)
_cell_angle_alpha     90
_cell_angle_beta     93.4610(10)
_cell_angle_gamma     90
_cell_volume     1723.67(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9683
_cell_measurement_theta_min     2.4099
_cell_measurement_theta_max     27.4913
_cell_measurement_temperature     296.(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.430
_exptl_crystal_size_mid     0.300
_exptl_crystal_size_min     0.220
_exptl_crystal_density_diffrn     1.258
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.078
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_shelx_estimated_absorpt_T_min     0.967
_shelx_estimated_absorpt_T_max     0.983
_exptl_absorpt_correction_T_min     0.87
_exptl_absorpt_correction_T_max     0.98
_exptl_special_details
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, collected 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 15 sec/frame.
;
_diffrn_ambient_temperature     296(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     30265
_diffrn_reflns_av_R_equivalents     0.0352
_diffrn_reflns_theta_min     2.055
_diffrn_reflns_theta_max     28.274
_diffrn_reflns_theta_full     28.200
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     25
_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. H-atoms attached to carbon
were placed in calculated positions (C---H = 0.95 - 0.99 Å). All were
included as riding contributions with isotropic displacement parameters
1.2 - 1.5 times those of the attached atoms.
;
_reflns_number_total     4261
_reflns_number_gt     3110
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0590
_refine_ls_R_factor_gt     0.0438
_refine_ls_wR_factor_gt     0.1290
_refine_ls_wR_factor_ref     0.1389
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     4261
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0823P)²+0.0650P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.210
_refine_diff_density_min     -0.154
_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
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (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 0.24295(7) 0.5688(2) 0.31026(6) 0.0954(4) Uani d 1 . .
    N N1 0.40947(6) 0.15215(15) 0.42752(5) 0.0473(2) Uani d 1 . .
    N N2 0.22089(6) 0.26574(17) 0.37616(4) 0.0514(3) Uani d 1 . .
    C C1 0.24093(7) 0.13976(19) 0.43604(5) 0.0458(3) Uani d 1 . .
    C C2 0.16861(8) 0.0487(2) 0.46964(6) 0.0577(3) Uani d 1 . .
    H H2 0.1091 0.0767 0.4532 0.069 Uiso calc 1 . .
    C C3 0.18363(10) -0.0813(2) 0.52644(7) 0.0663(4) Uani d 1 . .
    H H3 0.1346 -0.1407 0.5481 0.080 Uiso calc 1 . .
    C C4 0.27189(10) -0.1238(3) 0.55135(7) 0.0663(4) Uani d 1 . .
    H H4 0.2823 -0.2090 0.5904 0.080 Uiso calc 1 . .
    C C5 0.34419(9) -0.0404(2) 0.51839(6) 0.0565(3) Uani d 1 . .
    H H5 0.4033 -0.0731 0.5349 0.068 Uiso calc 1 . .
    C C6 0.33060(7) 0.09273(18) 0.46054(5) 0.0449(3) Uani d 1 . .
    C C7 0.41683(7) 0.35018(18) 0.40285(6) 0.0459(3) Uani d 1 . .
    C C8 0.34347(8) 0.5261(2) 0.40845(7) 0.0596(3) Uani d 1 . .
    H H8A 0.3241 0.5320 0.4543 0.071 Uiso calc 1 . .
    H H8B 0.3663 0.6739 0.3968 0.071 Uiso calc 1 . .
    C C9 0.26510(8) 0.4603(2) 0.36051(7) 0.0602(3) Uani d 1 . .
    C C10 0.49709(7) 0.40460(19) 0.36411(6) 0.0466(3) Uani d 1 . .
    C C11 0.53994(8) 0.6133(2) 0.36959(7) 0.0624(3) Uani d 1 . .
    H H11 0.5181 0.7232 0.3980 0.075 Uiso calc 1 . .
    C C12 0.61486(9) 0.6586(2) 0.33306(8) 0.0720(4) Uani d 1 . .
    H H12 0.6442 0.7974 0.3379 0.086 Uiso calc 1 . .
    C C13 0.64630(8) 0.5000(3) 0.28976(7) 0.0673(4) Uani d 1 . .
    H H13 0.6957 0.5331 0.2643 0.081 Uiso calc 1 . .
    C C14 0.60475(8) 0.2924(3) 0.28393(6) 0.0627(3) Uani d 1 . .
    H H14 0.6264 0.1845 0.2548 0.075 Uiso calc 1 . .
    C C15 0.53077(7) 0.2438(2) 0.32134(6) 0.0522(3) Uani d 1 . .
    H H15 0.5034 0.1022 0.3178 0.063 Uiso calc 1 . .
    C C16 0.14258(8) 0.1991(3) 0.33137(6) 0.0593(3) Uani d 1 . .
    H H16A 0.1336 0.0375 0.3358 0.071 Uiso calc 1 . .
    H H16B 0.1571 0.2284 0.2852 0.071 Uiso calc 1 . .
    C C17 0.05352(7) 0.3175(2) 0.34414(5) 0.0513(3) Uani d 1 . .
    C C18 0.04870(9) 0.5022(2) 0.38589(7) 0.0662(4) Uani d 1 . .
    H H18 0.1013 0.5564 0.4088 0.079 Uiso calc 1 . .
    C C19 -0.03416(9) 0.6081(3) 0.39392(8) 0.0759(4) Uani d 1 . .
    H H19 -0.0369 0.7328 0.4223 0.091 Uiso calc 1 . .
    C C20 -0.11235(9) 0.5294(3) 0.36009(8) 0.0704(4) Uani d 1 . .
    H H20 -0.1677 0.6016 0.3651 0.084 Uiso calc 1 . .
    C C21 -0.10814(8) 0.3448(3) 0.31912(7) 0.0668(4) Uani d 1 . .
    H H21 -0.1609 0.2900 0.2966 0.080 Uiso calc 1 . .
    C C22 -0.02581(8) 0.2394(2) 0.31100(6) 0.0595(3) Uani d 1 . .
    H H22 -0.0236 0.1141 0.2829 0.071 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 C9 . 1.2139(15) ?
    N1 C7 . 1.2773(14) ?
    N1 C6 . 1.4103(13) ?
    N2 C9 . 1.3672(16) ?
    N2 C1 . 1.4190(14) ?
    N2 C16 . 1.4653(15) ?
    C1 C2 . 1.3969(16) ?
    C1 C6 . 1.4048(15) ?
    C2 C3 . 1.3719(18) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.383(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.3731(19) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.3971(16) ?
    C5 H5 . 0.9300 ?
    C7 C10 . 1.4820(15) ?
    C7 C8 . 1.5078(15) ?
    C8 C9 . 1.5007(19) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C10 C15 . 1.3865(15) ?
    C10 C11 . 1.3879(17) ?
    C11 C12 . 1.3808(18) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.372(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.374(2) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.3836(17) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.5193(16) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 C18 . 1.3766(18) ?
    C17 C22 . 1.3832(17) ?
    C18 C19 . 1.3873(18) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.377(2) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.366(2) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.3795(18) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
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
    C7 N1 C6 . . 119.87(9) ?
    C9 N2 C1 . . 123.75(10) ?
    C9 N2 C16 . . 117.08(10) ?
    C1 N2 C16 . . 118.87(10) ?
    C2 C1 C6 . . 118.89(10) ?
    C2 C1 N2 . . 118.52(10) ?
    C6 C1 N2 . . 122.49(10) ?
    C3 C2 C1 . . 121.31(12) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    C2 C3 C4 . . 119.79(12) ?
    C2 C3 H3 . . 120.1 ?
    C4 C3 H3 . . 120.1 ?
    C5 C4 C3 . . 120.02(12) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 121.21(11) ?
    C4 C5 H5 . . 119.4 ?
    C6 C5 H5 . . 119.4 ?
    C5 C6 C1 . . 118.75(10) ?
    C5 C6 N1 . . 116.23(9) ?
    C1 C6 N1 . . 124.74(10) ?
    N1 C7 C10 . . 119.13(9) ?
    N1 C7 C8 . . 121.86(10) ?
    C10 C7 C8 . . 118.90(10) ?
    C9 C8 C7 . . 107.40(10) ?
    C9 C8 H8A . . 110.2 ?
    C7 C8 H8A . . 110.2 ?
    C9 C8 H8B . . 110.2 ?
    C7 C8 H8B . . 110.2 ?
    H8A C8 H8B . . 108.5 ?
    O1 C9 N2 . . 121.64(14) ?
    O1 C9 C8 . . 122.78(13) ?
    N2 C9 C8 . . 115.56(10) ?
    C15 C10 C11 . . 118.80(11) ?
    C15 C10 C7 . . 119.57(10) ?
    C11 C10 C7 . . 121.63(10) ?
    C12 C11 C10 . . 120.27(13) ?
    C12 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    C13 C12 C11 . . 120.40(13) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C12 C13 C14 . . 119.99(12) ?
    C12 C13 H13 . . 120.0 ?
    C14 C13 H13 . . 120.0 ?
    C13 C14 C15 . . 120.03(12) ?
    C13 C14 H14 . . 120.0 ?
    C15 C14 H14 . . 120.0 ?
    C14 C15 C10 . . 120.48(12) ?
    C14 C15 H15 . . 119.8 ?
    C10 C15 H15 . . 119.8 ?
    N2 C16 C17 . . 115.33(10) ?
    N2 C16 H16A . . 108.4 ?
    C17 C16 H16A . . 108.4 ?
    N2 C16 H16B . . 108.4 ?
    C17 C16 H16B . . 108.4 ?
    H16A C16 H16B . . 107.5 ?
    C18 C17 C22 . . 118.64(11) ?
    C18 C17 C16 . . 122.87(11) ?
    C22 C17 C16 . . 118.47(11) ?
    C17 C18 C19 . . 120.36(12) ?
    C17 C18 H18 . . 119.8 ?
    C19 C18 H18 . . 119.8 ?
    C20 C19 C18 . . 120.24(14) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C21 C20 C19 . . 119.65(12) ?
    C21 C20 H20 . . 120.2 ?
    C19 C20 H20 . . 120.2 ?
    C20 C21 C22 . . 120.21(12) ?
    C20 C21 H21 . . 119.9 ?
    C22 C21 H21 . . 119.9 ?
    C21 C22 C17 . . 120.89(13) ?
    C21 C22 H22 . . 119.6 ?
    C17 C22 H22 . . 119.6 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C9 N2 C1 C2 . . . . 139.33(12) ?
    C16 N2 C1 C2 . . . . -34.13(15) ?
    C9 N2 C1 C6 . . . . -44.34(16) ?
    C16 N2 C1 C6 . . . . 142.19(11) ?
    C6 C1 C2 C3 . . . . 1.24(19) ?
    N2 C1 C2 C3 . . . . 177.70(12) ?
    C1 C2 C3 C4 . . . . 0.1(2) ?
    C2 C3 C4 C5 . . . . -1.5(2) ?
    C3 C4 C5 C6 . . . . 1.6(2) ?
    C4 C5 C6 C1 . . . . -0.32(18) ?
    C4 C5 C6 N1 . . . . -174.53(12) ?
    C2 C1 C6 C5 . . . . -1.09(17) ?
    N2 C1 C6 C5 . . . . -177.40(10) ?
    C2 C1 C6 N1 . . . . 172.58(11) ?
    N2 C1 C6 N1 . . . . -3.73(17) ?
    C7 N1 C6 C5 . . . . -140.63(11) ?
    C7 N1 C6 C1 . . . . 45.55(15) ?
    C6 N1 C7 C10 . . . . -175.68(9) ?
    C6 N1 C7 C8 . . . . 0.61(16) ?
    N1 C7 C8 C9 . . . . -73.35(14) ?
    C10 C7 C8 C9 . . . . 102.95(11) ?
    C1 N2 C9 O1 . . . . -176.47(11) ?
    C16 N2 C9 O1 . . . . -2.89(17) ?
    C1 N2 C9 C8 . . . . 4.97(16) ?
    C16 N2 C9 C8 . . . . 178.55(9) ?
    C7 C8 C9 O1 . . . . -111.96(14) ?
    C7 C8 C9 N2 . . . . 66.58(13) ?
    N1 C7 C10 C15 . . . . 38.62(15) ?
    C8 C7 C10 C15 . . . . -137.79(12) ?
    N1 C7 C10 C11 . . . . -141.23(12) ?
    C8 C7 C10 C11 . . . . 42.37(16) ?
    C15 C10 C11 C12 . . . . -0.15(19) ?
    C7 C10 C11 C12 . . . . 179.70(11) ?
    C10 C11 C12 C13 . . . . 1.6(2) ?
    C11 C12 C13 C14 . . . . -1.8(2) ?
    C12 C13 C14 C15 . . . . 0.5(2) ?
    C13 C14 C15 C10 . . . . 1.00(18) ?
    C11 C10 C15 C14 . . . . -1.16(17) ?
    C7 C10 C15 C14 . . . . 178.99(10) ?
    C9 N2 C16 C17 . . . . -81.50(13) ?
    C1 N2 C16 C17 . . . . 92.40(13) ?
    N2 C16 C17 C18 . . . . 11.36(18) ?
    N2 C16 C17 C22 . . . . -170.31(11) ?
    C22 C17 C18 C19 . . . . -0.5(2) ?
    C16 C17 C18 C19 . . . . 177.85(13) ?
    C17 C18 C19 C20 . . . . -0.1(2) ?
    C18 C19 C20 C21 . . . . 0.7(2) ?
    C19 C20 C21 C22 . . . . -0.8(2) ?
    C20 C21 C22 C17 . . . . 0.2(2) ?
    C18 C17 C22 C21 . . . . 0.41(19) ?
    C16 C17 C22 C21 . . . . -177.99(12) ?
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
    C14 H14 O1 2_645 0.93 2.47 3.2808(17) 145
    C4 H4 Cg1 3_656 0.93 2.98 3.767(2) 143
