##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# 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     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2008-10-20
_journal_date_accepted     2008-11-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     12
_journal_page_first     o2356
_journal_page_last     o2356
_journal_paper_category     QO
_journal_coeditor_code     TK2318
_publ_contact_author_name     'Sabino, Jose R.'
_publ_contact_author_address
;
Instituto de F\'isica, UFG,
Caixa Postal 131,
74001-970, Goi\^ania
Brazil
;
_publ_contact_author_email     'jrsabino@if.ufg.br'
_publ_contact_author_fax     '55(62)35211014'
_publ_contact_author_phone     '55(62)35211014'
_publ_section_title
;\
1-Methyl-7-(4-nitrophenyl)-3-phenylpyrazolo[3,4-<i>b</i>]pyrrolo[3,4-<i>d</i>]\
pyridine-6,8(3<i>H</i>,7<i>H</i>)-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sabino, Jose R.' .
;
Instituto de F\'isica,
Universidade Federal de Goi\'as,
Caixa Postal 131,
74001-970, Goi\^ania, GO,
Brazil
;
    'Oliveira, Cec\'ilia M. A.' .
;
Instituto de Qu\'imica,
Universidade Federal de Goi\'as,
Caixa Postal 131, 74001-970,
Goi\^ania, GO, Brazil
;
    'Fraga, Carlos A. M.' .
;
Laboratory of Evaluation and Synthesis of Bioactive Substances
 (LASSBio), Faculdade de Farm\'acia,
Universidade Federal do Rio de Janeiro,
Caixa Postal 68023,
21944-971, Rio de Janeiro, RJ, Brazil
;
    'Barreiro, Eliezer J.' .
;
Laboratory of Evaluation and Synthesis of Bioactive Substances
 (LASSBio), Faculdade de Farm\'acia,
Universidade Federal do Rio de Janeiro,
Caixa Postal 68023,
21944-971, Rio de Janeiro, RJ, Brazil
;
    'Oliveira, Val\'eria de' .
;
Faculdade de Farm\'acia,
Universidade Federal de Goi\'as,
Caixa Postal 131, 74001-970,
Goi\^ania, GO, Brazil
;
    'Menegatti, Ricardo' .
;
Faculdade de Farm\'acia,
Universidade Federal de Goi\'as,
Caixa Postal 131, 74001-970,
Goi\^ania, GO, Brazil
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
1-Methyl-7-(4-nitrophenyl)-3-phenylpyrazolo[3,4-<i>b</i>]pyrrolo[3,4-
<i>d</i>]pyridine-6,8(3<i>H</i>,7<i>H</i>)-dione
;
_chemical_formula_moiety     'C21 H13 N5 O4'
_chemical_formula_sum     'C21 H13 N5 O4'
_chemical_formula_iupac     'C21 H13 N5 O4'
_chemical_formula_weight     399.36
_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     9.677(2)
_cell_length_b     12.141(3)
_cell_length_c     17.438(4)
_cell_angle_alpha     90
_cell_angle_beta     119.451(16)
_cell_angle_gamma     90
_cell_volume     1784.0(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     14.8
_cell_measurement_theta_max     40.8
_cell_measurement_temperature     297(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.1
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.487
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     0.892
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     297(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_device     '\k-geometry diffractometer'
_diffrn_measurement_method     'Non-profiled \w/2\w'
_diffrn_reflns_number     3813
_diffrn_reflns_av_R_equivalents     0.023
_diffrn_reflns_theta_min     4.66
_diffrn_reflns_theta_max     67.9
_diffrn_reflns_theta_full     67.9
_diffrn_measured_fraction_theta_max     1
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     1
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     2
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    0 5 -2
    1 6 0
_reflns_number_total     3259
_reflns_number_gt     2578
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.049
_refine_ls_wR_factor_ref     0.198
_refine_ls_goodness_of_fit_ref     1.07
_refine_ls_restrained_S_all     1.07
_refine_ls_number_reflns     3259
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[\s^2^(Fo^2^)+(0.152P)^2^+0.0892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_diff_density_max     0.48
_refine_diff_density_min     -0.38
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0114(15)
_refine_ls_extinction_expression
                                    Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4-PC (Enraf--Nonius, 1993)'
_computing_cell_refinement     'CAD-4-PC (Enraf--Nonius, 1993)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 C3 -0.0408(3) 0.00360(19) 0.37884(14) 0.0446(5) Uani d . 1 . .
    C C4 0.1214(3) 0.00403(18) 0.44674(14) 0.0425(5) Uani d . 1 . .
    C C5 0.1708(3) -0.10707(19) 0.45566(14) 0.0431(5) Uani d . 1 . .
    C C7 0.4230(3) -0.07508(19) 0.56234(16) 0.0500(6) Uani d . 1 . .
    H H7 0.5254 -0.0987 0.6016 0.06 Uiso calc R 1 . .
    C C8 0.3874(3) 0.03680(18) 0.55955(14) 0.0452(5) Uani d . 1 . .
    C C9 0.4917(3) 0.13014(18) 0.61003(15) 0.0455(5) Uani d . 1 . .
    C C11 0.2390(3) 0.19832(18) 0.51522(14) 0.0442(5) Uani d . 1 . .
    C C12 0.2381(3) 0.07694(18) 0.50241(14) 0.0427(5) Uani d . 1 . .
    C C13 0.0263(3) -0.28159(19) 0.37880(16) 0.0462(5) Uani d . 1 . .
    C C14 0.0917(3) -0.3569(2) 0.44682(16) 0.0514(6) Uani d . 1 . .
    H H14 0.1508 -0.3332 0.5049 0.062 Uiso calc R 1 . .
    C C15 0.0681(3) -0.4684(2) 0.42733(19) 0.0584(7) Uani d . 1 . .
    H H15 0.1132 -0.5198 0.4726 0.07 Uiso calc R 1 . .
    C C16 -0.0219(3) -0.5039(2) 0.3414(2) 0.0606(7) Uani d . 1 . .
    H H16 -0.0394 -0.5787 0.3289 0.073 Uiso calc R 1 . .
    C C17 -0.0852(3) -0.4279(2) 0.27450(19) 0.0616(7) Uani d . 1 . .
    H H17 -0.1454 -0.4516 0.2165 0.074 Uiso calc R 1 . .
    C C18 -0.0604(3) -0.3157(2) 0.29235(16) 0.0542(6) Uani d . 1 . .
    H H18 -0.1016 -0.2645 0.2468 0.065 Uiso calc R 1 . .
    C C19 -0.1519(3) 0.0984(2) 0.34157(17) 0.0549(6) Uani d . 1 . .
    H H19A -0.2592 0.0727 0.3172 0.082 Uiso calc R 1 . .
    H H19B -0.1383 0.1329 0.2962 0.082 Uiso calc R 1 . .
    H H19C -0.13 0.1509 0.3874 0.082 Uiso calc R 1 . .
    C C21 0.4456(3) 0.33472(18) 0.60655(14) 0.0426(5) Uani d . 1 . .
    C C22 0.3722(3) 0.3988(2) 0.64181(16) 0.0489(5) Uani d . 1 . .
    H H22 0.2948 0.3685 0.6523 0.059 Uiso calc R 1 . .
    C C23 0.4150(3) 0.5083(2) 0.66135(16) 0.0507(6) Uani d . 1 . .
    H H23 0.3682 0.5525 0.6859 0.061 Uiso calc R 1 . .
    C C24 0.5284(3) 0.55016(18) 0.64357(14) 0.0461(5) Uani d . 1 . .
    C C25 0.6055(3) 0.4867(2) 0.61069(15) 0.0496(6) Uani d . 1 . .
    H H25 0.6842 0.5169 0.6012 0.06 Uiso calc R 1 . .
    C C26 0.5631(3) 0.37726(19) 0.59215(15) 0.0480(5) Uani d . 1 . .
    H H26 0.6134 0.3325 0.5701 0.058 Uiso calc R 1 . .
    O O20 0.6301(2) 0.12980(14) 0.66441(12) 0.0587(5) Uani d . 1 . .
    O O27 0.1327(2) 0.26369(14) 0.47771(13) 0.0592(5) Uani d . 1 . .
    O O30 0.6424(2) 0.70822(16) 0.62526(14) 0.0675(6) Uani d . 1 . .
    N N1 0.0428(2) -0.16562(16) 0.39668(12) 0.0469(5) Uani d . 1 . .
    N N2 -0.0858(2) -0.09733(17) 0.34974(13) 0.0497(5) Uani d . 1 . .
    N N6 0.3155(2) -0.14946(16) 0.51075(13) 0.0489(5) Uani d . 1 . .
    N N10 0.3932(2) 0.22413(15) 0.58107(12) 0.0453(5) Uani d . 1 . .
    N N28 0.5686(3) 0.66741(18) 0.65876(13) 0.0561(6) Uani d . 1 . .
    O O29 0.5258(3) 0.71978(17) 0.70287(16) 0.0830(7) Uani d . 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
    C3 0.0414(11) 0.0460(11) 0.0430(11) 0.0022(9) 0.0181(9) 0.0009(9)
    C4 0.0394(11) 0.0436(11) 0.0430(11) 0.0017(9) 0.0190(9) 0.0022(9)
    C5 0.0401(11) 0.0427(11) 0.0459(11) 0.0016(9) 0.0207(9) 0.0017(9)
    C7 0.0398(11) 0.0408(11) 0.0580(13) 0.0049(9) 0.0152(10) 0.0057(9)
    C8 0.0418(11) 0.0406(11) 0.0479(11) 0.0017(9) 0.0180(10) 0.0039(9)
    C9 0.0436(12) 0.0393(12) 0.0490(12) 0.0048(9) 0.0192(10) 0.0033(9)
    C11 0.0407(11) 0.0425(12) 0.0464(11) 0.0035(9) 0.0191(9) 0.0036(9)
    C12 0.0410(11) 0.0411(11) 0.0444(11) 0.0046(9) 0.0196(9) 0.0045(8)
    C13 0.0411(11) 0.0424(12) 0.0567(12) -0.0020(9) 0.0252(10) -0.0056(9)
    C14 0.0511(13) 0.0476(13) 0.0544(13) -0.0011(10) 0.0250(11) -0.0023(10)
    C15 0.0586(15) 0.0462(13) 0.0755(17) 0.0040(11) 0.0368(13) 0.0043(12)
    C16 0.0550(14) 0.0457(13) 0.0872(19) -0.0057(11) 0.0397(14) -0.0145(12)
    C17 0.0524(14) 0.0661(17) 0.0650(15) -0.0068(12) 0.0280(12) -0.0226(13)
    C18 0.0492(13) 0.0567(14) 0.0548(13) -0.0003(11) 0.0241(11) -0.0034(11)
    C19 0.0426(12) 0.0534(14) 0.0545(13) 0.0090(10) 0.0130(11) 0.0022(10)
    C21 0.0389(11) 0.0386(11) 0.0436(10) 0.0011(8) 0.0152(9) 0.0014(8)
    C22 0.0469(12) 0.0464(12) 0.0550(12) -0.0016(10) 0.0264(11) -0.0028(10)
    C23 0.0475(12) 0.0483(12) 0.0530(12) 0.0023(10) 0.0222(10) -0.0079(10)
    C24 0.0420(11) 0.0390(11) 0.0441(11) -0.0020(9) 0.0109(9) -0.0046(9)
    C25 0.0441(12) 0.0463(12) 0.0581(13) -0.0018(9) 0.0248(11) 0.0008(10)
    C26 0.0454(12) 0.0457(12) 0.0528(12) 0.0029(10) 0.0241(10) -0.0026(10)
    O20 0.0414(9) 0.0510(10) 0.0623(11) 0.0035(7) 0.0089(8) 0.0036(7)
    O27 0.0457(9) 0.0434(9) 0.0709(11) 0.0100(7) 0.0152(8) 0.0002(8)
    O30 0.0607(11) 0.0490(10) 0.0811(13) -0.0093(9) 0.0258(10) 0.0001(9)
    N1 0.0415(10) 0.0421(10) 0.0497(10) -0.0009(8) 0.0167(8) -0.0029(8)
    N2 0.0411(10) 0.0498(11) 0.0498(10) 0.0019(8) 0.0159(9) -0.0013(8)
    N6 0.0420(10) 0.0395(9) 0.0568(11) 0.0039(8) 0.0178(9) 0.0014(8)
    N10 0.0408(10) 0.0379(10) 0.0493(10) 0.0013(8) 0.0161(8) 0.0012(7)
    N28 0.0528(12) 0.0460(11) 0.0535(11) -0.0040(9) 0.0139(10) -0.0058(9)
    O29 0.1122(19) 0.0534(11) 0.0905(15) -0.0043(12) 0.0553(15) -0.0207(10)
_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
    C3 N2 . 1.316(3) y
    C3 C4 . 1.428(3) y
    C3 C19 . 1.489(3) ?
    C4 C12 . 1.387(3) y
    C4 C5 . 1.414(3) ?
    C5 N6 . 1.351(3) ?
    C5 N1 . 1.358(3) ?
    C7 N6 . 1.337(3) y
    C7 C8 . 1.396(3) ?
    C7 H7 . 0.93 ?
    C8 C12 . 1.379(3) ?
    C8 C9 . 1.484(3) y
    C9 O20 . 1.202(3) ?
    C9 N10 . 1.411(3) ?
    C11 O27 . 1.206(3) ?
    C11 N10 . 1.400(3) ?
    C11 C12 . 1.490(3) y
    C13 C18 . 1.380(3) ?
    C13 C14 . 1.380(3) ?
    C13 N1 . 1.434(3) ?
    C14 C15 . 1.387(3) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.381(4) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.373(4) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.392(4) ?
    C17 H17 . 0.93 ?
    C18 H18 . 0.93 ?
    C19 H19A . 0.96 ?
    C19 H19B . 0.96 ?
    C19 H19C . 0.96 ?
    C21 C26 . 1.380(3) ?
    C21 C22 . 1.385(3) ?
    C21 N10 . 1.427(3) ?
    C22 C23 . 1.384(3) ?
    C22 H22 . 0.93 ?
    C23 C24 . 1.376(4) ?
    C23 H23 . 0.93 ?
    C24 C25 . 1.378(3) ?
    C24 N28 . 1.465(3) ?
    C25 C26 . 1.382(3) ?
    C25 H25 . 0.93 ?
    C26 H26 . 0.93 ?
    O30 N28 . 1.228(3) y
    N1 N2 . 1.380(3) ?
    N28 O29 . 1.216(3) y
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
    N2 C3 C4 . . 110.1(2) ?
    N2 C3 C19 . . 121.4(2) ?
    C4 C3 C19 . . 128.5(2) ?
    C12 C4 C5 . . 114.68(19) ?
    C12 C4 C3 . . 140.1(2) ?
    C5 C4 C3 . . 105.19(19) ?
    N6 C5 N1 . . 125.4(2) ?
    N6 C5 C4 . . 128.1(2) ?
    N1 C5 C4 . . 106.44(19) ?
    N6 C7 C8 . . 122.5(2) ?
    N6 C7 H7 . . 118.8 ?
    C8 C7 H7 . . 118.8 ?
    C12 C8 C7 . . 121.5(2) ?
    C12 C8 C9 . . 108.9(2) ?
    C7 C8 C9 . . 129.6(2) ?
    O20 C9 N10 . . 125.4(2) ?
    O20 C9 C8 . . 129.4(2) ?
    N10 C9 C8 . . 105.23(18) ?
    O27 C11 N10 . . 125.4(2) ?
    O27 C11 C12 . . 129.0(2) ?
    N10 C11 C12 . . 105.65(18) ?
    C8 C12 C4 . . 118.9(2) ?
    C8 C12 C11 . . 108.3(2) ?
    C4 C12 C11 . . 132.8(2) ?
    C18 C13 C14 . . 121.1(2) ?
    C18 C13 N1 . . 118.3(2) ?
    C14 C13 N1 . . 120.6(2) ?
    C13 C14 C15 . . 119.0(2) ?
    C13 C14 H14 . . 120.5 ?
    C15 C14 H14 . . 120.5 ?
    C16 C15 C14 . . 120.7(2) ?
    C16 C15 H15 . . 119.6 ?
    C14 C15 H15 . . 119.6 ?
    C17 C16 C15 . . 119.4(2) ?
    C17 C16 H16 . . 120.3 ?
    C15 C16 H16 . . 120.3 ?
    C16 C17 C18 . . 120.8(3) ?
    C16 C17 H17 . . 119.6 ?
    C18 C17 H17 . . 119.6 ?
    C13 C18 C17 . . 118.9(2) ?
    C13 C18 H18 . . 120.6 ?
    C17 C18 H18 . . 120.6 ?
    C3 C19 H19A . . 109.5 ?
    C3 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C3 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C26 C21 C22 . . 121.3(2) ?
    C26 C21 N10 . . 119.6(2) ?
    C22 C21 N10 . . 119.1(2) ?
    C23 C22 C21 . . 119.5(2) ?
    C23 C22 H22 . . 120.2 ?
    C21 C22 H22 . . 120.2 ?
    C24 C23 C22 . . 118.3(2) ?
    C24 C23 H23 . . 120.8 ?
    C22 C23 H23 . . 120.8 ?
    C23 C24 C25 . . 122.8(2) ?
    C23 C24 N28 . . 119.2(2) ?
    C25 C24 N28 . . 117.9(2) ?
    C24 C25 C26 . . 118.4(2) ?
    C24 C25 H25 . . 120.8 ?
    C26 C25 H25 . . 120.8 ?
    C21 C26 C25 . . 119.6(2) ?
    C21 C26 H26 . . 120.2 ?
    C25 C26 H26 . . 120.2 ?
    C5 N1 N2 . . 110.82(18) ?
    C5 N1 C13 . . 129.86(19) ?
    N2 N1 C13 . . 119.32(18) ?
    C3 N2 N1 . . 107.44(18) ?
    C7 N6 C5 . . 114.4(2) ?
    C11 N10 C9 . . 111.87(18) ?
    C11 N10 C21 . . 122.56(18) ?
    C9 N10 C21 . . 125.15(19) ?
    O29 N28 O30 . . 123.2(2) ?
    O29 N28 C24 . . 118.7(2) ?
    O30 N28 C24 . . 118.1(2) ?
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
    N2 C3 C4 C12 . . . . 179.4(3) ?
    C19 C3 C4 C12 . . . . -0.2(5) ?
    N2 C3 C4 C5 . . . . 0.3(3) ?
    C19 C3 C4 C5 . . . . -179.4(2) ?
    C12 C4 C5 N6 . . . . -0.3(3) ?
    C3 C4 C5 N6 . . . . 179.1(2) ?
    C12 C4 C5 N1 . . . . -179.93(19) ?
    C3 C4 C5 N1 . . . . -0.5(2) ?
    N6 C7 C8 C12 . . . . -0.4(4) ?
    N6 C7 C8 C9 . . . . -178.5(2) ?
    C12 C8 C9 O20 . . . . -178.1(3) ?
    C7 C8 C9 O20 . . . . 0.2(4) ?
    C12 C8 C9 N10 . . . . 2.0(3) ?
    C7 C8 C9 N10 . . . . -179.7(2) ?
    C7 C8 C12 C4 . . . . 0.0(3) ?
    C9 C8 C12 C4 . . . . 178.5(2) ?
    C7 C8 C12 C11 . . . . -179.7(2) ?
    C9 C8 C12 C11 . . . . -1.2(2) ?
    C5 C4 C12 C8 . . . . 0.3(3) ?
    C3 C4 C12 C8 . . . . -178.8(3) ?
    C5 C4 C12 C11 . . . . 179.9(2) ?
    C3 C4 C12 C11 . . . . 0.9(5) ?
    O27 C11 C12 C8 . . . . 179.4(2) ?
    N10 C11 C12 C8 . . . . 0.0(2) ?
    O27 C11 C12 C4 . . . . -0.3(4) ?
    N10 C11 C12 C4 . . . . -179.6(2) ?
    C18 C13 C14 C15 . . . . -0.5(4) ?
    N1 C13 C14 C15 . . . . 177.4(2) ?
    C13 C14 C15 C16 . . . . -1.1(4) ?
    C14 C15 C16 C17 . . . . 1.5(4) ?
    C15 C16 C17 C18 . . . . -0.3(4) ?
    C14 C13 C18 C17 . . . . 1.8(4) ?
    N1 C13 C18 C17 . . . . -176.2(2) ?
    C16 C17 C18 C13 . . . . -1.4(4) ?
    C26 C21 C22 C23 . . . . 1.4(4) ?
    N10 C21 C22 C23 . . . . -175.8(2) ?
    C21 C22 C23 C24 . . . . 1.0(4) ?
    C22 C23 C24 C25 . . . . -2.8(4) ?
    C22 C23 C24 N28 . . . . 176.4(2) ?
    C23 C24 C25 C26 . . . . 2.2(4) ?
    N28 C24 C25 C26 . . . . -177.0(2) ?
    C22 C21 C26 C25 . . . . -2.0(3) ?
    N10 C21 C26 C25 . . . . 175.2(2) ?
    C24 C25 C26 C21 . . . . 0.2(3) ?
    N6 C5 N1 N2 . . . . -179.1(2) ?
    C4 C5 N1 N2 . . . . 0.6(2) ?
    N6 C5 N1 C13 . . . . 1.1(4) ?
    C4 C5 N1 C13 . . . . -179.2(2) ?
    C18 C13 N1 C5 . . . . -140.1(2) ?
    C14 C13 N1 C5 . . . . 41.9(4) ?
    C18 C13 N1 N2 . . . . 40.1(3) ?
    C14 C13 N1 N2 . . . . -137.9(2) ?
    C4 C3 N2 N1 . . . . 0.1(3) ?
    C19 C3 N2 N1 . . . . 179.8(2) ?
    C5 N1 N2 C3 . . . . -0.4(3) ?
    C13 N1 N2 C3 . . . . 179.4(2) ?
    C8 C7 N6 C5 . . . . 0.4(4) ?
    N1 C5 N6 C7 . . . . 179.5(2) ?
    C4 C5 N6 C7 . . . . -0.1(4) ?
    O27 C11 N10 C9 . . . . -178.1(2) ?
    C12 C11 N10 C9 . . . . 1.3(2) ?
    O27 C11 N10 C21 . . . . -5.2(4) ?
    C12 C11 N10 C21 . . . . 174.2(2) ?
    O20 C9 N10 C11 . . . . 178.1(2) ?
    C8 C9 N10 C11 . . . . -2.0(3) ?
    O20 C9 N10 C21 . . . . 5.4(4) ?
    C8 C9 N10 C21 . . . . -174.7(2) ?
    C26 C21 N10 C11 . . . . -115.1(2) ?
    C22 C21 N10 C11 . . . . 62.1(3) ?
    C26 C21 N10 C9 . . . . 56.9(3) ?
    C22 C21 N10 C9 . . . . -125.9(2) ?
    C23 C24 N28 O29 . . . . 14.8(3) ?
    C25 C24 N28 O29 . . . . -166.1(2) ?
    C23 C24 N28 O30 . . . . -164.4(2) ?
    C25 C24 N28 O30 . . . . 14.8(3) ?
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
    C7 H7 O30 1_545 0.93 2.55 3.216(3) 129 y
    C18 H18 O30 4_465 0.93 2.44 3.197(3) 139 y