##############################################################################
#                                                                            #
# 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.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2013-07-23
_journal_date_accepted     2013-07-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      9
_journal_page_first     o1380
_journal_page_last     o1381
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813021181
_journal_coeditor_code     SU2627
_publ_contact_author_name     'K. Sethusankar'
_publ_contact_author_address
;
   Department of Physics
   RKM Vivekananda College (Autonomous)
   Chennai 600 004
   India
;
_publ_contact_author_email     'ksethusankar@yahoo.co.in'
_publ_contact_author_fax     '044 091 2499 3057'
_publ_contact_author_phone     '044 091 24484170'
_publ_section_title
;\
(4<i>S</i>*)-2-Methylamino-3-nitro-4-(4-nitrophenyl)-5,6,7,8-tetrahydro-\
4<i>H</i>-chromen-5-one
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Narayanan'
;  Department of Physics
   RKM Vivekananda College (Autonomous)
   Chennai 600 004
   India
;
    'Jayabal Kamalraja'
;
    Organic Chemistry Division
    Central Leather Research Institute
    Adyar
    Chennai 600 020
    India
;
    'Paramasivam T. Perumal'
;
    Organic Chemistry Division
    Central Leather Research Institute
    Adyar
    Chennai 600 020
    India
;
    'K. Sethusankar'
;   Department of Physics
    RKM Vivekananda College (Autonomous)
    Chennai 600 004
    India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;\
(4<i>S</i>*)-2-Methylamino-3-nitro-4-(4-nitrophenyl)-5,6,7,8-tetrahydro-\
4<i>H</i>-chromen-5-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H15 N3 O6'
_chemical_formula_sum     'C16 H15 N3 O6'
_chemical_formula_iupac     'C16 H15 N3 O6'
_chemical_formula_weight     345.31
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.2587(3)
_cell_length_b     8.7679(4)
_cell_length_c     10.9346(5)
_cell_angle_alpha     101.616(2)
_cell_angle_beta     90.426(2)
_cell_angle_gamma     91.930(2)
_cell_volume     775.05(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2633
_cell_measurement_theta_min     1.90
_cell_measurement_theta_max     26.43
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.480
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.966
_exptl_absorpt_correction_T_max     0.977
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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 APEXII CCD'
_diffrn_measurement_method     '\w and \f scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10840
_diffrn_reflns_av_R_equivalents     0.0261
_diffrn_reflns_av_sigmaI/netI     0.0227
_diffrn_reflns_theta_min     1.90
_diffrn_reflns_theta_max     26.43
_diffrn_reflns_theta_full     26.43
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3161
_reflns_number_gt     2633
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0525
_refine_ls_R_factor_gt     0.0444
_refine_ls_wR_factor_gt     0.1178
_refine_ls_wR_factor_ref     0.1261
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     3161
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.2861P] where P=(Fo^2^+2Fc^2^)/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     0.244
_refine_diff_density_min     -0.313
_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     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
and Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.2531(2) 1.32368(19) 0.26884(15) 0.0403(4) Uani d . 1 1 . .
    H H1 0.1710 1.3834 0.3094 0.048 Uiso calc R 1 1 . .
    C C2 0.3654(2) 1.3910(2) 0.20151(16) 0.0453(4) Uani d . 1 1 . .
    H H2 0.3626 1.4961 0.1983 0.054 Uiso calc R 1 1 . .
    C C3 0.48192(19) 1.2977(2) 0.13907(15) 0.0427(4) Uani d . 1 1 . .
    C C4 0.49206(19) 1.1433(2) 0.14415(16) 0.0431(4) Uani d . 1 1 . .
    H H4 0.5719 1.0831 0.1008 0.052 Uiso calc R 1 1 . .
    C C5 0.38164(18) 1.07952(19) 0.21467(15) 0.0373(4) Uani d . 1 1 . .
    H H5 0.3883 0.9756 0.2206 0.045 Uiso calc R 1 1 . .
    C C6 0.26034(17) 1.16853(17) 0.27713(13) 0.0317(3) Uani d . 1 1 . .
    C C7 0.13772(17) 1.09405(17) 0.35343(14) 0.0326(3) Uani d . 1 1 . .
    H H7 0.0602 1.1724 0.3894 0.039 Uiso calc R 1 1 . .
    C C8 0.04677(17) 0.96034(18) 0.27041(13) 0.0330(3) Uani d . 1 1 . .
    C C9 -0.07332(18) 0.9969(2) 0.18054(15) 0.0386(4) Uani d . 1 1 . .
    C C10 -0.1554(2) 0.8623(2) 0.09238(16) 0.0456(4) Uani d . 1 1 . .
    H H10A -0.1777 0.8934 0.0138 0.055 Uiso calc R 1 1 . .
    H H10B -0.2583 0.8373 0.1271 0.055 Uiso calc R 1 1 . .
    C C11 -0.0557(2) 0.7178(2) 0.06734(15) 0.0446(4) Uani d . 1 1 . .
    H H11A 0.0400 0.7369 0.0210 0.054 Uiso calc R 1 1 . .
    H H11B -0.1188 0.6322 0.0170 0.054 Uiso calc R 1 1 . .
    C C12 -0.0052(2) 0.6741(2) 0.18949(15) 0.0434(4) Uani d . 1 1 . .
    H H12A -0.0992 0.6358 0.2284 0.052 Uiso calc R 1 1 . .
    H H12B 0.0720 0.5918 0.1732 0.052 Uiso calc R 1 1 . .
    C C13 0.06922(18) 0.81242(18) 0.27499(14) 0.0349(3) Uani d . 1 1 . .
    C C14 0.23414(18) 0.87924(18) 0.45824(14) 0.0337(3) Uani d . 1 1 . .
    C C15 0.21916(18) 1.03614(17) 0.45763(13) 0.0336(3) Uani d . 1 1 . .
    C C16 0.3124(3) 0.6535(2) 0.5443(2) 0.0685(6) Uani d . 1 1 . .
    H H16A 0.2041 0.6094 0.5407 0.103 Uiso calc R 1 1 . .
    H H16B 0.3655 0.6397 0.6195 0.103 Uiso calc R 1 1 . .
    H H16C 0.3714 0.6023 0.4733 0.103 Uiso calc R 1 1 . .
    N N1 0.30687(19) 0.81832(17) 0.54344(13) 0.0445(4) Uani d D 1 1 . .
    N N2 0.28580(17) 1.14864(16) 0.55398(12) 0.0405(3) Uani d . 1 1 . .
    N N3 0.5987(2) 1.3655(3) 0.06260(18) 0.0627(5) Uani d . 1 1 . .
    O O1 0.16935(14) 0.76920(13) 0.36371(10) 0.0414(3) Uani d . 1 1 . .
    O O2 -0.10506(16) 1.13167(16) 0.18180(13) 0.0544(4) Uani d . 1 1 . .
    O O3 0.36526(17) 1.11096(15) 0.64145(11) 0.0535(3) Uani d . 1 1 . .
    O O4 0.26560(19) 1.28774(14) 0.55197(12) 0.0579(4) Uani d . 1 1 . .
    O O5 0.6313(2) 1.5047(2) 0.09323(18) 0.0934(6) Uani d . 1 1 . .
    O O6 0.6534(2) 1.2794(2) -0.02896(18) 0.0874(6) Uani d . 1 1 . .
    H H1A 0.349(4) 0.891(3) 0.607(2) 0.105 Uiso d D 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0438(9) 0.0379(8) 0.0401(8) 0.0039(7) 0.0024(7) 0.0098(7)
    C2 0.0522(10) 0.0400(9) 0.0465(9) -0.0063(7) -0.0046(8) 0.0169(7)
    C3 0.0304(8) 0.0616(11) 0.0399(9) -0.0091(7) -0.0057(6) 0.0211(8)
    C4 0.0287(7) 0.0606(11) 0.0427(9) 0.0075(7) 0.0012(6) 0.0160(8)
    C5 0.0337(8) 0.0403(8) 0.0403(8) 0.0053(6) -0.0028(6) 0.0130(7)
    C6 0.0303(7) 0.0371(8) 0.0286(7) -0.0006(6) -0.0050(5) 0.0092(6)
    C7 0.0314(7) 0.0348(8) 0.0330(7) 0.0036(6) 0.0009(6) 0.0098(6)
    C8 0.0266(7) 0.0424(8) 0.0315(7) -0.0011(6) -0.0005(6) 0.0118(6)
    C9 0.0273(7) 0.0544(10) 0.0384(8) 0.0018(6) 0.0008(6) 0.0195(7)
    C10 0.0316(8) 0.0687(12) 0.0383(9) -0.0011(7) -0.0075(7) 0.0161(8)
    C11 0.0370(8) 0.0606(11) 0.0343(8) -0.0054(7) -0.0050(6) 0.0064(7)
    C12 0.0449(9) 0.0439(9) 0.0401(9) -0.0054(7) -0.0076(7) 0.0071(7)
    C13 0.0308(7) 0.0435(9) 0.0315(7) -0.0017(6) -0.0045(6) 0.0109(6)
    C14 0.0327(7) 0.0401(8) 0.0289(7) 0.0003(6) -0.0026(6) 0.0086(6)
    C15 0.0346(7) 0.0383(8) 0.0281(7) -0.0011(6) -0.0003(6) 0.0077(6)
    C16 0.0977(17) 0.0461(11) 0.0639(13) 0.0088(11) -0.0315(12) 0.0169(9)
    N1 0.0549(9) 0.0423(8) 0.0374(7) 0.0031(6) -0.0136(6) 0.0110(6)
    N2 0.0481(8) 0.0424(8) 0.0307(7) -0.0034(6) -0.0006(6) 0.0073(5)
    N3 0.0397(8) 0.0917(14) 0.0665(11) -0.0157(9) -0.0052(8) 0.0423(10)
    O1 0.0487(7) 0.0369(6) 0.0386(6) 0.0019(5) -0.0142(5) 0.0083(5)
    O2 0.0471(7) 0.0585(8) 0.0637(8) 0.0068(6) -0.0117(6) 0.0261(6)
    O3 0.0675(8) 0.0560(8) 0.0356(6) -0.0060(6) -0.0162(6) 0.0079(5)
    O4 0.0883(10) 0.0372(7) 0.0461(7) -0.0028(6) -0.0066(7) 0.0044(5)
    O5 0.0823(12) 0.1065(14) 0.0976(13) -0.0536(11) -0.0110(10) 0.0455(11)
    O6 0.0651(10) 0.1239(16) 0.0858(12) 0.0141(10) 0.0369(9) 0.0481(11)
_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 C2 . 1.378(2) ?
    C1 C6 . 1.385(2) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.379(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.371(3) ?
    C3 N3 . 1.469(2) ?
    C4 C5 . 1.374(2) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.388(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.528(2) ?
    C7 C15 . 1.501(2) ?
    C7 C8 . 1.505(2) ?
    C7 H7 . 0.9800 ?
    C8 C13 . 1.327(2) ?
    C8 C9 . 1.479(2) ?
    C9 O2 . 1.216(2) ?
    C9 C10 . 1.504(2) ?
    C10 C11 . 1.514(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.521(2) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.486(2) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 O1 . 1.3877(18) ?
    C14 N1 . 1.314(2) ?
    C14 O1 . 1.3569(18) ?
    C14 C15 . 1.387(2) ?
    C15 N2 . 1.386(2) ?
    C16 N1 . 1.449(2) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    N1 H1A . 0.906(10) ?
    N2 O4 . 1.2411(18) ?
    N2 O3 . 1.2598(18) ?
    N3 O5 . 1.219(3) ?
    N3 O6 . 1.226(3) ?
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 C1 C6 . . 121.08(15) ?
    C2 C1 H1 . . 119.5 ?
    C6 C1 H1 . . 119.5 ?
    C3 C2 C1 . . 117.90(16) ?
    C3 C2 H2 . . 121.1 ?
    C1 C2 H2 . . 121.1 ?
    C4 C3 C2 . . 122.65(15) ?
    C4 C3 N3 . . 118.58(17) ?
    C2 C3 N3 . . 118.77(17) ?
    C3 C4 C5 . . 118.53(15) ?
    C3 C4 H4 . . 120.7 ?
    C5 C4 H4 . . 120.7 ?
    C4 C5 C6 . . 120.72(15) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C1 C6 C5 . . 119.08(14) ?
    C1 C6 C7 . . 121.28(13) ?
    C5 C6 C7 . . 119.64(13) ?
    C15 C7 C8 . . 109.22(12) ?
    C15 C7 C6 . . 111.43(12) ?
    C8 C7 C6 . . 110.03(12) ?
    C15 C7 H7 . . 108.7 ?
    C8 C7 H7 . . 108.7 ?
    C6 C7 H7 . . 108.7 ?
    C13 C8 C9 . . 119.05(14) ?
    C13 C8 C7 . . 122.96(13) ?
    C9 C8 C7 . . 117.99(13) ?
    O2 C9 C8 . . 120.00(15) ?
    O2 C9 C10 . . 122.51(14) ?
    C8 C9 C10 . . 117.46(14) ?
    C9 C10 C11 . . 113.25(13) ?
    C9 C10 H10A . . 108.9 ?
    C11 C10 H10A . . 108.9 ?
    C9 C10 H10B . . 108.9 ?
    C11 C10 H10B . . 108.9 ?
    H10A C10 H10B . . 107.7 ?
    C10 C11 C12 . . 110.42(14) ?
    C10 C11 H11A . . 109.6 ?
    C12 C11 H11A . . 109.6 ?
    C10 C11 H11B . . 109.6 ?
    C12 C11 H11B . . 109.6 ?
    H11A C11 H11B . . 108.1 ?
    C13 C12 C11 . . 109.88(14) ?
    C13 C12 H12A . . 109.7 ?
    C11 C12 H12A . . 109.7 ?
    C13 C12 H12B . . 109.7 ?
    C11 C12 H12B . . 109.7 ?
    H12A C12 H12B . . 108.2 ?
    C8 C13 O1 . . 122.42(13) ?
    C8 C13 C12 . . 126.12(14) ?
    O1 C13 C12 . . 111.46(13) ?
    N1 C14 O1 . . 112.44(13) ?
    N1 C14 C15 . . 127.25(14) ?
    O1 C14 C15 . . 120.30(13) ?
    N2 C15 C14 . . 120.33(13) ?
    N2 C15 C7 . . 116.49(13) ?
    C14 C15 C7 . . 123.14(13) ?
    N1 C16 H16A . . 109.5 ?
    N1 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    N1 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C14 N1 C16 . . 125.65(15) ?
    C14 N1 H1A . . 112.9(19) ?
    C16 N1 H1A . . 121.4(19) ?
    O4 N2 O3 . . 120.65(13) ?
    O4 N2 C15 . . 118.39(14) ?
    O3 N2 C15 . . 120.96(14) ?
    O5 N3 O6 . . 124.64(19) ?
    O5 N3 C3 . . 117.5(2) ?
    O6 N3 C3 . . 117.88(19) ?
    C14 O1 C13 . . 119.94(12) ?
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
    C6 C1 C2 C3 . . . . 2.2(2) ?
    C1 C2 C3 C4 . . . . -1.6(3) ?
    C1 C2 C3 N3 . . . . 177.53(15) ?
    C2 C3 C4 C5 . . . . -0.2(2) ?
    N3 C3 C4 C5 . . . . -179.32(15) ?
    C3 C4 C5 C6 . . . . 1.4(2) ?
    C2 C1 C6 C5 . . . . -1.0(2) ?
    C2 C1 C6 C7 . . . . 178.99(14) ?
    C4 C5 C6 C1 . . . . -0.8(2) ?
    C4 C5 C6 C7 . . . . 179.15(14) ?
    C1 C6 C7 C15 . . . . -118.64(15) ?
    C5 C6 C7 C15 . . . . 61.39(18) ?
    C1 C6 C7 C8 . . . . 120.07(15) ?
    C5 C6 C7 C8 . . . . -59.91(17) ?
    C15 C7 C8 C13 . . . . -14.1(2) ?
    C6 C7 C8 C13 . . . . 108.47(16) ?
    C15 C7 C8 C9 . . . . 165.53(12) ?
    C6 C7 C8 C9 . . . . -71.87(16) ?
    C13 C8 C9 O2 . . . . 174.08(15) ?
    C7 C8 C9 O2 . . . . -5.6(2) ?
    C13 C8 C9 C10 . . . . -4.3(2) ?
    C7 C8 C9 C10 . . . . 176.08(13) ?
    O2 C9 C10 C11 . . . . 155.85(16) ?
    C8 C9 C10 C11 . . . . -25.9(2) ?
    C9 C10 C11 C12 . . . . 53.46(19) ?
    C10 C11 C12 C13 . . . . -50.56(19) ?
    C9 C8 C13 O1 . . . . -174.42(13) ?
    C7 C8 C13 O1 . . . . 5.2(2) ?
    C9 C8 C13 C12 . . . . 5.8(2) ?
    C7 C8 C13 C12 . . . . -174.55(15) ?
    C11 C12 C13 C8 . . . . 22.5(2) ?
    C11 C12 C13 O1 . . . . -157.33(14) ?
    N1 C14 C15 N2 . . . . 0.4(2) ?
    O1 C14 C15 N2 . . . . -179.78(13) ?
    N1 C14 C15 C7 . . . . 178.06(15) ?
    O1 C14 C15 C7 . . . . -2.1(2) ?
    C8 C7 C15 N2 . . . . -169.66(12) ?
    C6 C7 C15 N2 . . . . 68.58(17) ?
    C8 C7 C15 C14 . . . . 12.6(2) ?
    C6 C7 C15 C14 . . . . -109.17(16) ?
    O1 C14 N1 C16 . . . . -3.4(3) ?
    C15 C14 N1 C16 . . . . 176.41(19) ?
    C14 C15 N2 O4 . . . . -177.86(14) ?
    C7 C15 N2 O4 . . . . 4.3(2) ?
    C14 C15 N2 O3 . . . . 2.3(2) ?
    C7 C15 N2 O3 . . . . -175.54(14) ?
    C4 C3 N3 O5 . . . . -152.56(18) ?
    C2 C3 N3 O5 . . . . 28.3(2) ?
    C4 C3 N3 O6 . . . . 29.2(2) ?
    C2 C3 N3 O6 . . . . -150.02(19) ?
    N1 C14 O1 C13 . . . . 171.08(13) ?
    C15 C14 O1 C13 . . . . -8.8(2) ?
    C8 C13 O1 C14 . . . . 7.4(2) ?
    C12 C13 O1 C14 . . . . -172.82(14) ?
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
    N1 H1A O3 . 0.90(3) 1.89(3) 2.601(2) 134(2)
    C11 H11A O6 2_675 0.97 2.54 3.352(2) 141
    C11 H11B O5 1_445 0.97 2.54 3.186(2) 124
    C10 H10A Cg1 2_575 0.97 2.90 3.515(2) 135
    C16 H16B Cg1 2_676 0.96 2.90 3.577(3) 142