##############################################################################
###                                                                        ###
###        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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-07-11
_journal_date_accepted     2009-07-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      8
_journal_page_first     o1945
_journal_page_last     o1945
_journal_paper_category     QO
_journal_coeditor_code     BT2998
_publ_contact_author_name     ' M.N. Ponnuswamy '
_publ_contact_author_address
;   Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai - 600 025
    India
;
_publ_contact_author_email     'mnpsy2004@yahoo.com'
_publ_contact_author_fax     '+9144 22352494'
_publ_contact_author_phone     '+9144 22300122'
_publ_section_title
;\
1'-Methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-\
4',4'-dicarbonitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Ramesh'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'S. S. Sundaresan'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'N. Vidhya Lakshmi'
;
Organic Chemistry Division
Central Leather Research Institute
Adyar
Chennai 600 020
India
;
    'Paramasivan T. Perumal'
;
Organic Chemistry Division
Central Leather Research Institute
Adyar
Chennai 600 020
India
;
    'M. N. Ponnuswamy'
;
Centre of Advanced Study in Crystallography and Biophysics
University of Madras
Guindy Campus
Chennai 600 025
India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1'-Methyl-2,2''-dioxoindoline-3-spiro-2'-pyrrolidine-3'-spiro-3''-indoline-
4',4'-dicarbonitrile
;
_chemical_name_common
;
1N-Methyl-3,3-dicarbonitrile-4,5-dispirooxindolinpyrrolidine
;
_chemical_formula_moiety     'C21 H15 N5 O2'
_chemical_formula_sum     'C21 H15 N5 O2'
_chemical_formula_iupac     'C21 H15 N5 O2'
_chemical_formula_weight     369.38
_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     13.3173(3)
_cell_length_b     9.9480(2)
_cell_length_c     13.3950(3)
_cell_angle_alpha     90.00
_cell_angle_beta     91.8270(10)
_cell_angle_gamma     90.00
_cell_volume     1773.67(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3546
_cell_measurement_theta_min     2.12
_cell_measurement_theta_max     33.49
_cell_measurement_temperature     293(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     1.383
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     768
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     'Multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.972
_exptl_absorpt_correction_T_max     0.982
_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     'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     26314
_diffrn_reflns_av_R_equivalents     0.0302
_diffrn_reflns_av_sigmaI/netI     0.0356
_diffrn_reflns_theta_min     2.12
_diffrn_reflns_theta_max     33.49
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_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 >
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     6939
_reflns_number_gt     4820
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0780
_refine_ls_R_factor_gt     0.0500
_refine_ls_wR_factor_gt     0.1243
_refine_ls_wR_factor_ref     0.1421
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     6939
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0723P)²+0.242P] 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     0.012
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.377
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0042(12)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.62030(6) 0.88197(10) 0.24064(7) 0.0387(2) Uani d . 1 . .
    O O2 0.24158(6) 0.73812(9) 0.25781(7) 0.03117(19) Uani d . 1 . .
    N N1 0.59318(8) 0.75699(11) 0.09828(8) 0.0329(2) Uani d . 1 . .
    H H1 0.6578(14) 0.7468(18) 0.0787(14) 0.058(5) Uiso d . 1 . .
    C C2 0.56573(8) 0.82292(11) 0.18087(8) 0.0270(2) Uani d . 1 . .
    C C3 0.44951(7) 0.81058(11) 0.18735(7) 0.02235(19) Uani d . 1 . .
    C C4 0.42192(8) 0.73937(11) 0.09067(8) 0.0254(2) Uani d . 1 . .
    C C5 0.33077(10) 0.71016(14) 0.04484(9) 0.0352(3) Uani d . 1 . .
    H H5 0.2712 0.7316 0.0755 0.042 Uiso calc R 1 . .
    C C6 0.32903(11) 0.64796(15) -0.04818(10) 0.0417(3) Uani d . 1 . .
    H H6 0.2679 0.6272 -0.0799 0.050 Uiso calc R 1 . .
    C C7 0.41773(12) 0.61699(14) -0.09353(10) 0.0417(3) Uani d . 1 . .
    H H7 0.4153 0.5740 -0.1552 0.050 Uiso calc R 1 . .
    C C8 0.50971(11) 0.64808(13) -0.04977(9) 0.0362(3) Uani d . 1 . .
    H H8 0.5692 0.6283 -0.0811 0.043 Uiso calc R 1 . .
    C C9 0.51005(9) 0.70967(11) 0.04223(8) 0.0281(2) Uani d . 1 . .
    C C10 0.42527(7) 0.73565(10) 0.28602(7) 0.02080(18) Uani d . 1 . .
    C C11 0.31810(8) 0.67524(11) 0.27584(8) 0.0236(2) Uani d . 1 . .
    N N12 0.32571(7) 0.54152(10) 0.29159(8) 0.0301(2) Uani d . 1 . .
    H H12 0.2748(13) 0.4894(17) 0.2909(12) 0.045(4) Uiso d . 1 . .
    C C13 0.42464(8) 0.50270(11) 0.31500(8) 0.0273(2) Uani d . 1 . .
    C C14 0.45870(11) 0.37590(13) 0.33844(11) 0.0386(3) Uani d . 1 . .
    H H14 0.4152 0.3028 0.3391 0.046 Uiso calc R 1 . .
    C C15 0.55997(12) 0.36121(14) 0.36089(11) 0.0436(3) Uani d . 1 . .
    H H15 0.5852 0.2764 0.3767 0.052 Uiso calc R 1 . .
    C C16 0.62440(10) 0.46957(14) 0.36045(11) 0.0405(3) Uani d . 1 . .
    H H16 0.6923 0.4570 0.3762 0.049 Uiso calc R 1 . .
    C C17 0.58894(8) 0.59738(13) 0.33672(9) 0.0316(2) Uani d . 1 . .
    H H17 0.6325 0.6705 0.3365 0.038 Uiso calc R 1 . .
    C C18 0.48791(8) 0.61382(11) 0.31355(8) 0.0236(2) Uani d . 1 . .
    N N19 0.39864(7) 0.93947(9) 0.19956(6) 0.02403(18) Uani d . 1 . .
    C C20 0.41979(9) 0.98552(11) 0.30134(8) 0.0266(2) Uani d . 1 . .
    H H20A 0.3668 1.0442 0.3236 0.032 Uiso calc R 1 . .
    H H20B 0.4831 1.0336 0.3059 0.032 Uiso calc R 1 . .
    C C21 0.42485(8) 0.85489(11) 0.36474(8) 0.02283(19) Uani d U 1 . .
    C C22 0.42339(11) 1.04057(13) 0.12517(10) 0.0376(3) Uani d . 1 . .
    H H22A 0.4939 1.0603 0.1303 0.056 Uiso calc R 1 . .
    H H22B 0.3857 1.1210 0.1368 0.056 Uiso calc R 1 . .
    H H22C 0.4068 1.0068 0.0596 0.056 Uiso calc R 1 . .
    C C23 0.33963(8) 0.84184(12) 0.43191(8) 0.0281(2) Uani d U 1 . .
    N N24 0.27708(9) 0.82688(14) 0.48603(9) 0.0446(3) Uani d . 1 . .
    C C25 0.51485(8) 0.85674(11) 0.43181(8) 0.0268(2) Uani d U 1 . .
    N N26 0.57990(8) 0.86218(12) 0.48812(8) 0.0392(3) 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
    O1 C2 . 1.2154(14) ?
    O2 C11 . 1.2134(13) ?
    N1 C2 . 1.3467(15) ?
    N1 C9 . 1.3993(16) ?
    N1 H1 . 0.913(18) ?
    C2 C3 . 1.5578(15) ?
    C3 N19 . 1.4618(13) ?
    C3 C4 . 1.5111(15) ?
    C3 C10 . 1.5601(14) ?
    C4 C5 . 1.3738(17) ?
    C4 C9 . 1.3908(15) ?
    C5 C6 . 1.3908(18) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.380(2) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.376(2) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.3760(16) ?
    C8 H8 . 0.9300 ?
    C10 C18 . 1.5103(14) ?
    C10 C11 . 1.5505(14) ?
    C10 C21 . 1.5871(14) ?
    C11 N12 . 1.3502(14) ?
    N12 C13 . 1.3989(15) ?
    N12 H12 . 0.853(17) ?
    C13 C14 . 1.3735(16) ?
    C13 C18 . 1.3904(15) ?
    C14 C15 . 1.380(2) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.378(2) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.3896(18) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.3809(15) ?
    C17 H17 . 0.9300 ?
    N19 C20 . 1.4572(14) ?
    N19 C22 . 1.4607(14) ?
    C20 C21 . 1.5527(15) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 C25 . 1.4749(15) ?
    C21 C23 . 1.4763(15) ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
    C23 N24 . 1.1314(14) ?
    C25 N26 . 1.1317(15) ?
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 C9 . . 111.95(10) ?
    C2 N1 H1 . . 125.0(12) ?
    C9 N1 H1 . . 123.0(12) ?
    O1 C2 N1 . . 127.18(11) ?
    O1 C2 C3 . . 125.15(10) ?
    N1 C2 C3 . . 107.67(10) ?
    N19 C3 C4 . . 113.97(9) ?
    N19 C3 C2 . . 113.70(9) ?
    C4 C3 C2 . . 101.77(8) ?
    N19 C3 C10 . . 102.43(7) ?
    C4 C3 C10 . . 116.80(9) ?
    C2 C3 C10 . . 108.52(8) ?
    C5 C4 C9 . . 119.56(10) ?
    C5 C4 C3 . . 132.01(10) ?
    C9 C4 C3 . . 108.28(10) ?
    C4 C5 C6 . . 118.92(11) ?
    C4 C5 H5 . . 120.5 ?
    C6 C5 H5 . . 120.5 ?
    C7 C6 C5 . . 120.24(13) ?
    C7 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C8 C7 C6 . . 121.67(12) ?
    C8 C7 H7 . . 119.2 ?
    C6 C7 H7 . . 119.2 ?
    C9 C8 C7 . . 117.32(12) ?
    C9 C8 H8 . . 121.3 ?
    C7 C8 H8 . . 121.3 ?
    C8 C9 C4 . . 122.26(12) ?
    C8 C9 N1 . . 127.61(11) ?
    C4 C9 N1 . . 110.06(10) ?
    C18 C10 C11 . . 102.13(8) ?
    C18 C10 C3 . . 117.56(8) ?
    C11 C10 C3 . . 108.98(8) ?
    C18 C10 C21 . . 116.82(8) ?
    C11 C10 C21 . . 108.99(8) ?
    C3 C10 C21 . . 102.18(8) ?
    O2 C11 N12 . . 126.68(10) ?
    O2 C11 C10 . . 125.63(10) ?
    N12 C11 C10 . . 107.69(9) ?
    C11 N12 C13 . . 111.86(9) ?
    C11 N12 H12 . . 122.8(11) ?
    C13 N12 H12 . . 125.2(11) ?
    C14 C13 C18 . . 122.51(11) ?
    C14 C13 N12 . . 127.35(11) ?
    C18 C13 N12 . . 110.14(9) ?
    C13 C14 C15 . . 117.41(12) ?
    C13 C14 H14 . . 121.3 ?
    C15 C14 H14 . . 121.3 ?
    C16 C15 C14 . . 121.37(12) ?
    C16 C15 H15 . . 119.3 ?
    C14 C15 H15 . . 119.3 ?
    C15 C16 C17 . . 120.64(12) ?
    C15 C16 H16 . . 119.7 ?
    C17 C16 H16 . . 119.7 ?
    C18 C17 C16 . . 118.77(11) ?
    C18 C17 H17 . . 120.6 ?
    C16 C17 H17 . . 120.6 ?
    C17 C18 C13 . . 119.29(10) ?
    C17 C18 C10 . . 132.57(10) ?
    C13 C18 C10 . . 108.13(9) ?
    C20 N19 C22 . . 112.38(9) ?
    C20 N19 C3 . . 107.70(8) ?
    C22 N19 C3 . . 114.34(9) ?
    N19 C20 C21 . . 104.61(8) ?
    N19 C20 H20A . . 110.8 ?
    C21 C20 H20A . . 110.8 ?
    N19 C20 H20B . . 110.8 ?
    C21 C20 H20B . . 110.8 ?
    H20A C20 H20B . . 108.9 ?
    C25 C21 C23 . . 104.79(9) ?
    C25 C21 C20 . . 110.06(9) ?
    C23 C21 C20 . . 112.71(9) ?
    C25 C21 C10 . . 113.20(8) ?
    C23 C21 C10 . . 111.00(9) ?
    C20 C21 C10 . . 105.26(8) ?
    N19 C22 H22A . . 109.5 ?
    N19 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    N19 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    N24 C23 C21 . . 176.43(13) ?
    N26 C25 C21 . . 175.22(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
    C9 N1 C2 O1 . . . . -175.23(12) ?
    C9 N1 C2 C3 . . . . 4.82(13) ?
    O1 C2 C3 N19 . . . . 52.14(15) ?
    N1 C2 C3 N19 . . . . -127.91(10) ?
    O1 C2 C3 C4 . . . . 175.14(12) ?
    N1 C2 C3 C4 . . . . -4.91(11) ?
    O1 C2 C3 C10 . . . . -61.12(14) ?
    N1 C2 C3 C10 . . . . 118.84(10) ?
    N19 C3 C4 C5 . . . . -49.34(16) ?
    C2 C3 C4 C5 . . . . -172.16(13) ?
    C10 C3 C4 C5 . . . . 69.89(16) ?
    N19 C3 C4 C9 . . . . 126.17(10) ?
    C2 C3 C4 C9 . . . . 3.36(11) ?
    C10 C3 C4 C9 . . . . -114.60(10) ?
    C9 C4 C5 C6 . . . . 1.73(19) ?
    C3 C4 C5 C6 . . . . 176.83(12) ?
    C4 C5 C6 C7 . . . . -0.3(2) ?
    C5 C6 C7 C8 . . . . -1.1(2) ?
    C6 C7 C8 C9 . . . . 1.0(2) ?
    C7 C8 C9 C4 . . . . 0.43(19) ?
    C7 C8 C9 N1 . . . . -176.24(12) ?
    C5 C4 C9 C8 . . . . -1.83(18) ?
    C3 C4 C9 C8 . . . . -177.99(11) ?
    C5 C4 C9 N1 . . . . 175.36(11) ?
    C3 C4 C9 N1 . . . . -0.80(13) ?
    C2 N1 C9 C8 . . . . 174.33(12) ?
    C2 N1 C9 C4 . . . . -2.67(14) ?
    N19 C3 C10 C18 . . . . -163.79(9) ?
    C4 C3 C10 C18 . . . . 70.95(12) ?
    C2 C3 C10 C18 . . . . -43.27(12) ?
    N19 C3 C10 C11 . . . . 80.73(10) ?
    C4 C3 C10 C11 . . . . -44.53(12) ?
    C2 C3 C10 C11 . . . . -158.75(8) ?
    N19 C3 C10 C21 . . . . -34.50(9) ?
    C4 C3 C10 C21 . . . . -159.76(8) ?
    C2 C3 C10 C21 . . . . 86.02(9) ?
    C18 C10 C11 O2 . . . . 177.12(10) ?
    C3 C10 C11 O2 . . . . -57.82(14) ?
    C21 C10 C11 O2 . . . . 52.93(14) ?
    C18 C10 C11 N12 . . . . -2.28(11) ?
    C3 C10 C11 N12 . . . . 122.78(9) ?
    C21 C10 C11 N12 . . . . -126.47(9) ?
    O2 C11 N12 C13 . . . . -177.24(11) ?
    C10 C11 N12 C13 . . . . 2.15(13) ?
    C11 N12 C13 C14 . . . . 177.75(12) ?
    C11 N12 C13 C18 . . . . -1.10(14) ?
    C18 C13 C14 C15 . . . . -0.1(2) ?
    N12 C13 C14 C15 . . . . -178.85(13) ?
    C13 C14 C15 C16 . . . . 0.4(2) ?
    C14 C15 C16 C17 . . . . -0.3(2) ?
    C15 C16 C17 C18 . . . . 0.0(2) ?
    C16 C17 C18 C13 . . . . 0.28(18) ?
    C16 C17 C18 C10 . . . . 179.26(12) ?
    C14 C13 C18 C17 . . . . -0.21(18) ?
    N12 C13 C18 C17 . . . . 178.72(10) ?
    C14 C13 C18 C10 . . . . -179.42(11) ?
    N12 C13 C18 C10 . . . . -0.49(13) ?
    C11 C10 C18 C17 . . . . -177.43(12) ?
    C3 C10 C18 C17 . . . . 63.40(16) ?
    C21 C10 C18 C17 . . . . -58.64(16) ?
    C11 C10 C18 C13 . . . . 1.63(11) ?
    C3 C10 C18 C13 . . . . -117.54(10) ?
    C21 C10 C18 C13 . . . . 120.42(10) ?
    C4 C3 N19 C20 . . . . 171.14(9) ?
    C2 C3 N19 C20 . . . . -72.83(10) ?
    C10 C3 N19 C20 . . . . 44.04(10) ?
    C4 C3 N19 C22 . . . . -63.21(12) ?
    C2 C3 N19 C22 . . . . 52.83(13) ?
    C10 C3 N19 C22 . . . . 169.69(9) ?
    C22 N19 C20 C21 . . . . -161.08(9) ?
    C3 N19 C20 C21 . . . . -34.26(10) ?
    N19 C20 C21 C25 . . . . 132.70(9) ?
    N19 C20 C21 C23 . . . . -110.72(10) ?
    N19 C20 C21 C10 . . . . 10.40(10) ?
    C18 C10 C21 C25 . . . . 24.19(12) ?
    C11 C10 C21 C25 . . . . 139.22(9) ?
    C3 C10 C21 C25 . . . . -105.56(9) ?
    C18 C10 C21 C23 . . . . -93.33(11) ?
    C11 C10 C21 C23 . . . . 21.70(12) ?
    C3 C10 C21 C23 . . . . 136.92(9) ?
    C18 C10 C21 C20 . . . . 144.44(9) ?
    C11 C10 C21 C20 . . . . -100.54(9) ?
    C3 C10 C21 C20 . . . . 14.69(10) ?
    C25 C21 C23 N24 . . . . -44(2) ?
    C20 C21 C23 N24 . . . . -164(2) ?
    C10 C21 C23 N24 . . . . 78(2) ?
    C23 C21 C25 N26 . . . . -30.2(16) ?
    C20 C21 C25 N26 . . . . 91.2(16) ?
    C10 C21 C25 N26 . . . . -151.3(15) ?
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
    C5 H5 O2 1 0.93 2.49 3.1371(15) 127.2
    C17 H17 O1 1 0.93 2.47 3.1433(16) 129.7
    C20 H20B O1 1 0.97 2.54 2.9986(14) 108.6
    C22 H22B O2 2 0.96 2.53 3.3713(15) 147.0
    N12 H12 O2 2_545 0.853(17) 2.591(17) 3.2114(13) 130.5(14)
    N12 H12 N19 2_545 0.853(17) 2.371(17) 3.1613(13) 154.4(15)
    C14 H14 O2 2_545 0.93 2.51 3.2305(16) 134.7
    N1 H1 N24 4_675 0.913(18) 2.174(18) 3.0315(15) 156.1(16)
    C7 H7 Cg5 3_556 0.93 2.8374 3.5366(15) 156.21
