##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2009-04-20
_journal_date_accepted     2009-04-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o1163
_journal_page_last     o1164
_journal_paper_category     QO
_journal_coeditor_code     AT2770
_publ_contact_author_name     'Nilantha Lakshman'
_publ_contact_author_address
;
Department of  Food science and Technology
Faculty of Agriculture
University of Ruhuna
Mapalana
Kamburupitiya (81100)
Sri Lanka.
;
_publ_contact_author_email     nilanthalakshman@yahoo.co.uk
_publ_contact_author_fax     '+94-41-2292384'
_publ_contact_author_phone     '+94-41-2292200'
_publ_section_title
;\
13-Hydroxy-4,16-dimethyl-4,16-diazapentacyclo[12.3.1.0^1,5^.0^5,13^.0^7,12^]\
octadeca-7(12),8,10-triene-6,18-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'J. Suresh' .
;
Department of Physics
The Madura College
Madurai 625 011
India
;
    'K. Gurunathan' .
;
Department of Physics
The Madura College
Madurai 625 011
India
;
    'R. Suresh Kumar' .
;
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
    'S. Perumal' .
;
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
    'P. L. Nilantha Lakshman' .
;
Department of Food Science and Technology
Faculty of Agriculture
University of Ruhuna
Mapalana
Kamburupitiya 81100
Sri Lanka
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
13-Hydroxy-4,16-dimethyl-4,16-
diazapentacyclo[12.3.1.0^1,5^.0^5,13^.0^7,12^]octadeca-
7(12),8,10-triene-6,18-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H20 N2 O3'
_chemical_formula_sum     'C18 H20 N2 O3'
_chemical_formula_iupac     'C18 H20 N2 O3'
_chemical_formula_weight     312.36
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     11.0862(5)
_cell_length_b     11.6152(5)
_cell_length_c     12.5670(6)
_cell_angle_alpha     90.00
_cell_angle_beta     102.851(9)
_cell_angle_gamma     90.00
_cell_volume     1577.70(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     2
_cell_measurement_theta_max     25
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.315
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9839
_exptl_absorpt_correction_T_max     0.9901
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Nonius MACH-3'
_diffrn_measurement_method     ω-2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3226
_diffrn_reflns_av_R_equivalents     0.0455
_diffrn_reflns_av_sigmaI/netI     0.0266
_diffrn_reflns_theta_min     2.22
_diffrn_reflns_theta_max     24.97
_diffrn_reflns_theta_full     24.97
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     2
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_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 >
σ(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     2764
_reflns_number_gt     1978
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0613
_refine_ls_R_factor_gt     0.0394
_refine_ls_wR_factor_gt     0.1074
_refine_ls_wR_factor_ref     0.1204
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     2764
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0616P)²+0.2971P] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.155
_refine_diff_density_min     -0.181
_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     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.37990(16) 0.05350(16) 0.64487(16) 0.0558(5) Uani d . 1 . .
    C C2 0.25684(15) 0.03912(14) 0.56351(16) 0.0496(4) Uani d . 1 . .
    C C3 0.15940(16) 0.06258(15) 0.63055(15) 0.0517(4) Uani d . 1 . .
    H H3A 0.0772 0.0460 0.5874 0.062 Uiso calc R 1 . .
    H H3B 0.1744 0.0143 0.6951 0.062 Uiso calc R 1 . .
    C C4 0.39217(16) 0.18110(16) 0.66421(15) 0.0537(5) Uani d . 1 . .
    H H4 0.4750 0.2026 0.7051 0.064 Uiso calc R 1 . .
    C C5 0.29116(17) 0.21625(17) 0.72388(14) 0.0554(5) Uani d . 1 . .
    H H5A 0.3067 0.1796 0.7950 0.067 Uiso calc R 1 . .
    H H5B 0.2935 0.2989 0.7349 0.067 Uiso calc R 1 . .
    C C6 0.36690(14) 0.22296(15) 0.54459(15) 0.0471(4) Uani d . 1 . .
    C C7 0.26099(14) 0.14067(15) 0.48444(13) 0.0461(4) Uani d . 1 . .
    C C8 0.14614(15) 0.21810(16) 0.45590(13) 0.0471(4) Uani d . 1 . .
    C C9 0.18837(16) 0.33902(15) 0.47548(14) 0.0475(4) Uani d . 1 . .
    C C10 0.31366(16) 0.34242(15) 0.52472(14) 0.0472(4) Uani d . 1 . .
    C C11 0.37277(19) 0.44677(16) 0.54870(16) 0.0595(5) Uani d . 1 . .
    H H11 0.4564 0.4498 0.5824 0.071 Uiso calc R 1 . .
    C C12 0.3053(2) 0.54695(17) 0.52175(17) 0.0680(6) Uani d . 1 . .
    H H12 0.3445 0.6178 0.5363 0.082 Uiso calc R 1 . .
    C C13 0.1808(2) 0.54309(18) 0.47352(17) 0.0688(6) Uani d . 1 . .
    H H13 0.1369 0.6114 0.4570 0.083 Uiso calc R 1 . .
    C C14 0.12088(19) 0.43966(18) 0.44954(16) 0.0602(5) Uani d . 1 . .
    H H14 0.0370 0.4372 0.4167 0.072 Uiso calc R 1 . .
    C C15 0.24197(18) -0.07110(18) 0.49582(19) 0.0671(6) Uani d . 1 . .
    H H15A 0.3119 -0.1222 0.5203 0.080 Uiso calc R 1 . .
    H H15B 0.1667 -0.1113 0.5006 0.080 Uiso calc R 1 . .
    C C16 0.2361(2) -0.0302(2) 0.3805(2) 0.0798(7) Uani d . 1 . .
    H H16A 0.2811 -0.0824 0.3431 0.096 Uiso calc R 1 . .
    H H16B 0.1509 -0.0260 0.3397 0.096 Uiso calc R 1 . .
    C C17 0.2705(2) 0.1496(2) 0.28884(17) 0.0845(7) Uani d . 1 . .
    H H17A 0.1830 0.1563 0.2602 0.127 Uiso calc R 1 . .
    H H17B 0.3075 0.1103 0.2369 0.127 Uiso calc R 1 . .
    H H17C 0.3061 0.2249 0.3025 0.127 Uiso calc R 1 . .
    C C18 0.06767(19) 0.2233(2) 0.70672(18) 0.0693(6) Uani d . 1 . .
    H H18A -0.0089 0.2123 0.6544 0.104 Uiso calc R 1 . .
    H H18B 0.0787 0.3036 0.7240 0.104 Uiso calc R 1 . .
    H H18C 0.0660 0.1808 0.7719 0.104 Uiso calc R 1 . .
    N N1 0.16914(13) 0.18280(12) 0.66132(11) 0.0479(4) Uani d . 1 . .
    N N2 0.29314(14) 0.08429(15) 0.39070(13) 0.0603(4) Uani d . 1 . .
    O O1 0.04209(10) 0.18577(12) 0.41422(11) 0.0618(4) Uani d . 1 . .
    O O2 0.47670(10) 0.20956(13) 0.50608(13) 0.0650(4) Uani d . 1 . .
    H H2 0.4673 0.1578 0.4606 0.098 Uiso calc R 1 . .
    O O3 0.45072(13) -0.02185(13) 0.68415(14) 0.0810(5) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 O3 . 1.206(2) ?
    C1 C4 . 1.503(3) ?
    C1 C2 . 1.521(2) ?
    C2 C15 . 1.526(3) ?
    C2 C3 . 1.535(3) ?
    C2 C7 . 1.549(3) ?
    C3 N1 . 1.446(2) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.535(3) ?
    C4 C6 . 1.545(3) ?
    C4 H4 . 0.9800 ?
    C5 N1 . 1.458(2) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 O2 . 1.415(2) ?
    C6 C10 . 1.507(2) ?
    C6 C7 . 1.571(2) ?
    C7 N2 . 1.460(2) ?
    C7 C8 . 1.535(2) ?
    C8 O1 . 1.2154(19) ?
    C8 C9 . 1.484(3) ?
    C9 C14 . 1.387(3) ?
    C9 C10 . 1.390(2) ?
    C10 C11 . 1.379(3) ?
    C11 C12 . 1.384(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.379(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.374(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.513(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 N2 . 1.466(3) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 N2 . 1.461(3) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 N1 . 1.448(2) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    O2 H2 . 0.8200 ?
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
    O3 C1 C4 . . 128.48(17) ?
    O3 C1 C2 . . 126.90(18) ?
    C4 C1 C2 . . 104.62(14) ?
    C1 C2 C15 . . 115.87(15) ?
    C1 C2 C3 . . 104.30(15) ?
    C15 C2 C3 . . 116.94(15) ?
    C1 C2 C7 . . 101.38(13) ?
    C15 C2 C7 . . 107.23(16) ?
    C3 C2 C7 . . 109.99(14) ?
    N1 C3 C2 . . 107.36(14) ?
    N1 C3 H3A . . 110.2 ?
    C2 C3 H3A . . 110.2 ?
    N1 C3 H3B . . 110.2 ?
    C2 C3 H3B . . 110.2 ?
    H3A C3 H3B . . 108.5 ?
    C1 C4 C5 . . 106.95(15) ?
    C1 C4 C6 . . 99.36(15) ?
    C5 C4 C6 . . 113.42(14) ?
    C1 C4 H4 . . 112.1 ?
    C5 C4 H4 . . 112.1 ?
    C6 C4 H4 . . 112.1 ?
    N1 C5 C4 . . 110.85(14) ?
    N1 C5 H5A . . 109.5 ?
    C4 C5 H5A . . 109.5 ?
    N1 C5 H5B . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 108.1 ?
    O2 C6 C10 . . 112.31(14) ?
    O2 C6 C4 . . 108.33(14) ?
    C10 C6 C4 . . 115.51(15) ?
    O2 C6 C7 . . 112.10(14) ?
    C10 C6 C7 . . 104.91(13) ?
    C4 C6 C7 . . 103.35(13) ?
    N2 C7 C8 . . 114.40(14) ?
    N2 C7 C2 . . 102.91(14) ?
    C8 C7 C2 . . 117.03(14) ?
    N2 C7 C6 . . 111.76(13) ?
    C8 C7 C6 . . 104.37(14) ?
    C2 C7 C6 . . 106.28(13) ?
    O1 C8 C9 . . 126.74(16) ?
    O1 C8 C7 . . 125.32(17) ?
    C9 C8 C7 . . 107.53(13) ?
    C14 C9 C10 . . 120.94(17) ?
    C14 C9 C8 . . 128.68(16) ?
    C10 C9 C8 . . 110.36(14) ?
    C11 C10 C9 . . 120.10(17) ?
    C11 C10 C6 . . 128.58(16) ?
    C9 C10 C6 . . 111.31(14) ?
    C10 C11 C12 . . 118.75(19) ?
    C10 C11 H11 . . 120.6 ?
    C12 C11 H11 . . 120.6 ?
    C13 C12 C11 . . 120.90(19) ?
    C13 C12 H12 . . 119.6 ?
    C11 C12 H12 . . 119.6 ?
    C14 C13 C12 . . 120.86(19) ?
    C14 C13 H13 . . 119.6 ?
    C12 C13 H13 . . 119.6 ?
    C13 C14 C9 . . 118.43(19) ?
    C13 C14 H14 . . 120.8 ?
    C9 C14 H14 . . 120.8 ?
    C16 C15 C2 . . 104.31(17) ?
    C16 C15 H15A . . 110.9 ?
    C2 C15 H15A . . 110.9 ?
    C16 C15 H15B . . 110.9 ?
    C2 C15 H15B . . 110.9 ?
    H15A C15 H15B . . 108.9 ?
    N2 C16 C15 . . 105.95(17) ?
    N2 C16 H16A . . 110.5 ?
    C15 C16 H16A . . 110.5 ?
    N2 C16 H16B . . 110.5 ?
    C15 C16 H16B . . 110.5 ?
    H16A C16 H16B . . 108.7 ?
    N2 C17 H17A . . 109.5 ?
    N2 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    N2 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    N1 C18 H18A . . 109.5 ?
    N1 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    N1 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C3 N1 C18 . . 113.60(15) ?
    C3 N1 C5 . . 113.99(14) ?
    C18 N1 C5 . . 114.19(15) ?
    C7 N2 C17 . . 116.69(17) ?
    C7 N2 C16 . . 107.45(16) ?
    C17 N2 C16 . . 114.03(18) ?
    C6 O2 H2 . . 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
    O3 C1 C2 C15 . . . . -22.8(3) ?
    C4 C1 C2 C15 . . . . 157.13(17) ?
    O3 C1 C2 C3 . . . . 107.2(2) ?
    C4 C1 C2 C3 . . . . -72.83(18) ?
    O3 C1 C2 C7 . . . . -138.5(2) ?
    C4 C1 C2 C7 . . . . 41.44(18) ?
    C1 C2 C3 N1 . . . . 66.97(17) ?
    C15 C2 C3 N1 . . . . -163.63(15) ?
    C7 C2 C3 N1 . . . . -41.05(18) ?
    O3 C1 C4 C5 . . . . -112.9(2) ?
    C2 C1 C4 C5 . . . . 67.20(18) ?
    O3 C1 C4 C6 . . . . 129.0(2) ?
    C2 C1 C4 C6 . . . . -50.92(17) ?
    C1 C4 C5 N1 . . . . -56.50(19) ?
    C6 C4 C5 N1 . . . . 52.0(2) ?
    C1 C4 C6 O2 . . . . -80.09(16) ?
    C5 C4 C6 O2 . . . . 166.74(14) ?
    C1 C4 C6 C10 . . . . 152.95(14) ?
    C5 C4 C6 C10 . . . . 39.8(2) ?
    C1 C4 C6 C7 . . . . 38.98(16) ?
    C5 C4 C6 C7 . . . . -74.19(17) ?
    C1 C2 C7 N2 . . . . 102.34(15) ?
    C15 C2 C7 N2 . . . . -19.57(17) ?
    C3 C2 C7 N2 . . . . -147.71(14) ?
    C1 C2 C7 C8 . . . . -131.31(15) ?
    C15 C2 C7 C8 . . . . 106.79(17) ?
    C3 C2 C7 C8 . . . . -21.4(2) ?
    C1 C2 C7 C6 . . . . -15.26(17) ?
    C15 C2 C7 C6 . . . . -137.16(14) ?
    C3 C2 C7 C6 . . . . 94.70(15) ?
    O2 C6 C7 N2 . . . . -9.8(2) ?
    C10 C6 C7 N2 . . . . 112.33(16) ?
    C4 C6 C7 N2 . . . . -126.26(15) ?
    O2 C6 C7 C8 . . . . -133.98(15) ?
    C10 C6 C7 C8 . . . . -11.83(17) ?
    C4 C6 C7 C8 . . . . 109.58(15) ?
    O2 C6 C7 C2 . . . . 101.72(16) ?
    C10 C6 C7 C2 . . . . -136.13(14) ?
    C4 C6 C7 C2 . . . . -14.72(16) ?
    N2 C7 C8 O1 . . . . 62.2(2) ?
    C2 C7 C8 O1 . . . . -58.3(2) ?
    C6 C7 C8 O1 . . . . -175.36(16) ?
    N2 C7 C8 C9 . . . . -110.88(16) ?
    C2 C7 C8 C9 . . . . 128.67(15) ?
    C6 C7 C8 C9 . . . . 11.57(17) ?
    O1 C8 C9 C14 . . . . -1.2(3) ?
    C7 C8 C9 C14 . . . . 171.71(17) ?
    O1 C8 C9 C10 . . . . -179.96(17) ?
    C7 C8 C9 C10 . . . . -7.01(19) ?
    C14 C9 C10 C11 . . . . 0.1(3) ?
    C8 C9 C10 C11 . . . . 178.94(16) ?
    C14 C9 C10 C6 . . . . -179.82(16) ?
    C8 C9 C10 C6 . . . . -1.0(2) ?
    O2 C6 C10 C11 . . . . -49.6(2) ?
    C4 C6 C10 C11 . . . . 75.3(2) ?
    C7 C6 C10 C11 . . . . -171.64(18) ?
    O2 C6 C10 C9 . . . . 130.29(15) ?
    C4 C6 C10 C9 . . . . -104.79(17) ?
    C7 C6 C10 C9 . . . . 8.28(18) ?
    C9 C10 C11 C12 . . . . -0.7(3) ?
    C6 C10 C11 C12 . . . . 179.21(17) ?
    C10 C11 C12 C13 . . . . 1.1(3) ?
    C11 C12 C13 C14 . . . . -0.9(3) ?
    C12 C13 C14 C9 . . . . 0.3(3) ?
    C10 C9 C14 C13 . . . . 0.1(3) ?
    C8 C9 C14 C13 . . . . -178.51(17) ?
    C1 C2 C15 C16 . . . . -113.14(18) ?
    C3 C2 C15 C16 . . . . 123.18(18) ?
    C7 C2 C15 C16 . . . . -0.81(19) ?
    C2 C15 C16 N2 . . . . 21.1(2) ?
    C2 C3 N1 C18 . . . . 168.67(15) ?
    C2 C3 N1 C5 . . . . -58.18(19) ?
    C4 C5 N1 C3 . . . . 53.1(2) ?
    C4 C5 N1 C18 . . . . -174.04(16) ?
    C8 C7 N2 C17 . . . . 35.0(2) ?
    C2 C7 N2 C17 . . . . 163.01(16) ?
    C6 C7 N2 C17 . . . . -83.3(2) ?
    C8 C7 N2 C16 . . . . -94.49(19) ?
    C2 C7 N2 C16 . . . . 33.53(18) ?
    C6 C7 N2 C16 . . . . 147.18(16) ?
    C15 C16 N2 C7 . . . . -35.3(2) ?
    C15 C16 N2 C17 . . . . -166.26(17) ?
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
    O2 H2 N2 . 0.82 2.12 2.655(2) 123
    C15 H15A O3 . 0.97 2.56 2.974(3) 106
    C18 H18B O3 2_556 0.96 2.39 3.288(3) 155
