##############################################################################
###                                                                        ###
###        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     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2010-07-21
_journal_date_accepted     2010-09-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     10
_journal_page_first     o2634
_journal_page_last     o2635
_journal_paper_category     QO
_journal_coeditor_code     BV2155
_publ_contact_author_name     'P. Thomas Muthiah'
_publ_contact_author_address
;School of Chemistry
Bharathidasan University
Tiruchirappalli-620 024
Tamil Nadu, India
;
_publ_contact_author_email     'tommtrichy@yahoo.co.in'
_publ_contact_author_fax     '0431-2407045'
_publ_contact_author_phone     '0431-2407053'
_publ_section_title
;
4,6-Dimethoxypyrimidin-2-amine--2-(1H-indol-3-yl)acetic acid (1/1)
;
loop_
    _publ_author_name
    _publ_author_address
    'Samuel Ebenezer'
;School of Chemistry
Bharathidasan University
Tiruchirappalli-620 024
Tamilnadu, India.
;
    'Packianathan Thomas Muthiah'
;School of Chemistry
Bharathidasan University
Tiruchirappalli-620 024
Tamilnadu, India.
;
data_I
_chemical_name_systematic
;
4,6-Dimethoxypyrimidin-2-amine--2-(1H-indol-3-yl)acetic acid (1/1)
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C10 H9 N O2, C6 H9 N3 O2'
_chemical_formula_sum     'C16 H18 N4 O4'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C10 H9 N O2, C6 H9 N3 O2'
_chemical_formula_weight     330.34
_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_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     7.45550(10)
_cell_length_b     10.7197(2)
_cell_length_c     11.2537(2)
_cell_angle_alpha     62.9810(10)
_cell_angle_beta     85.8630(10)
_cell_angle_gamma     85.5840(10)
_cell_volume     798.16(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5363
_cell_measurement_theta_min     2.0
_cell_measurement_theta_max     31.8
_cell_measurement_temperature     293
_cell_special_details
;
;
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.22
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.375
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     348
_exptl_absorpt_coefficient_mu     0.101
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.970
_exptl_absorpt_correction_T_max     0.978
_exptl_special_details
;
;
_diffrn_ambient_temperature     293
_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 area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19719
_diffrn_reflns_av_R_equivalents     0.0280
_diffrn_reflns_av_sigmaI/netI     0.0211
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     31.83
_diffrn_reflns_theta_full     31.83
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_reflns_reduction_process
;
;
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
Refinement on F² for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The observed criterion of F² > σ(F²)
is used only for calculating -R-factor-obs 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     5363
_reflns_number_gt     3979
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0622
_refine_ls_R_factor_gt     0.0461
_refine_ls_wR_factor_gt     0.1250
_refine_ls_wR_factor_ref     0.1373
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     5363
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0654P)²+0.0927P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.226
_refine_diff_density_min     -0.216
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 '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     'PLATON (Spek, 2009)'
_computing_publication_material     '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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O3 0.47314(13) 0.61367(8) 0.19523(8) 0.0511(3) Uani . . 1.000
    O O4 0.41360(15) 0.83007(9) 0.17016(9) 0.0610(3) Uani . . 1.000
    N N4 0.33691(16) 0.67797(12) -0.21918(11) 0.0549(4) Uani . . 1.000
    C C9 0.47507(14) 0.75081(11) 0.12695(11) 0.0401(3) Uani . . 1.000
    C C10 0.56115(15) 0.79980(13) -0.01155(11) 0.0458(3) Uani . . 1.000
    C C11 0.44583(15) 0.77265(11) -0.09994(11) 0.0409(3) Uani . . 1.000
    C C12 0.47745(18) 0.67593(13) -0.14708(13) 0.0514(4) Uani . . 1.000
    C C13 0.20837(16) 0.77659(11) -0.21974(11) 0.0429(3) Uani . . 1.000
    C C14 0.27307(14) 0.83893(10) -0.14517(10) 0.0372(3) Uani . . 1.000
    C C15 0.16352(16) 0.94084(11) -0.12571(11) 0.0438(3) Uani . . 1.000
    C C16 -0.00356(18) 0.97665(13) -0.17950(13) 0.0526(4) Uani . . 1.000
    C C17 -0.06486(18) 0.91367(14) -0.25289(14) 0.0567(4) Uani . . 1.000
    C C18 0.03945(18) 0.81345(14) -0.27433(13) 0.0532(4) Uani . . 1.000
    O O1 0.05798(14) 0.34071(10) 0.80461(9) 0.0602(3) Uani . . 1.000
    O O2 0.34975(14) 0.31388(9) 0.43080(9) 0.0556(3) Uani . . 1.000
    N N1 0.29633(12) 0.51850(9) 0.43555(8) 0.0385(2) Uani . . 1.000
    N N2 0.24541(15) 0.73208(10) 0.43481(10) 0.0492(3) Uani . . 1.000
    N N3 0.15054(12) 0.54001(10) 0.62253(9) 0.0421(3) Uani . . 1.000
    C C2 0.23037(13) 0.59256(10) 0.49907(10) 0.0368(3) Uani . . 1.000
    C C4 0.13751(15) 0.40253(12) 0.68250(11) 0.0433(3) Uani . . 1.000
    C C5 0.20213(16) 0.31430(11) 0.62803(11) 0.0450(3) Uani . . 1.000
    C C6 0.28114(14) 0.37938(11) 0.50225(11) 0.0398(3) Uani . . 1.000
    C C7 -0.0202(2) 0.42776(17) 0.86200(15) 0.0684(5) Uani . . 1.000
    C C8 0.3549(2) 0.16378(14) 0.49465(17) 0.0659(5) Uani . . 1.000
    H H3 0.41670 0.59300 0.26640 0.0770 Uiso calc R 1.000
    H H4 0.33010 0.62570 -0.25810 0.0660 Uiso calc R 1.000
    H H10A 0.57970 0.89940 -0.05000 0.0550 Uiso calc R 1.000
    H H10B 0.67780 0.75120 -0.00610 0.0550 Uiso calc R 1.000
    H H12 0.58030 0.61690 -0.13220 0.0620 Uiso calc R 1.000
    H H15 0.20310 0.98350 -0.07720 0.0530 Uiso calc R 1.000
    H H16 -0.07720 1.04400 -0.16680 0.0630 Uiso calc R 1.000
    H H17 -0.17860 0.94000 -0.28800 0.0680 Uiso calc R 1.000
    H H18 -0.00150 0.77200 -0.32350 0.0640 Uiso calc R 1.000
    H H2A 0.29580 0.77020 0.35610 0.0590 Uiso calc R 1.000
    H H2B 0.20460 0.78330 0.47240 0.0590 Uiso calc R 1.000
    H H5 0.19270 0.21760 0.67350 0.0540 Uiso calc R 1.000
    H H7A 0.07320 0.47350 0.87930 0.1030 Uiso calc R 1.000
    H H7B -0.08420 0.37130 0.94420 0.1030 Uiso calc R 1.000
    H H7C -0.10200 0.49700 0.80110 0.1030 Uiso calc R 1.000
    H H8A 0.42070 0.12850 0.57470 0.0990 Uiso calc R 1.000
    H H8B 0.41310 0.12980 0.43540 0.0990 Uiso calc R 1.000
    H H8C 0.23430 0.13240 0.51670 0.0990 Uiso calc R 1.000
_geom_special_details
;
Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O3 C9 . . 1.3142(15) no
    O4 C9 . . 1.2048(16) no
    O3 H3 . . 0.8200 no
    O1 C7 . . 1.427(2) no
    O1 C4 . . 1.3397(14) no
    O2 C6 . . 1.3415(16) no
    O2 C8 . . 1.432(2) no
    N4 C12 . . 1.3637(18) no
    N4 C13 . . 1.3693(18) no
    N4 H4 . . 0.8600 no
    N1 C2 . . 1.3371(15) no
    N1 C6 . . 1.3405(16) no
    N2 C2 . . 1.3431(16) no
    N3 C2 . . 1.3502(13) no
    N3 C4 . . 1.3213(17) no
    N2 H2B . . 0.8600 no
    N2 H2A . . 0.8600 no
    C9 C10 . . 1.5103(16) no
    C10 C11 . . 1.4961(17) no
    C11 C14 . . 1.4311(16) no
    C11 C12 . . 1.362(2) no
    C13 C14 . . 1.4146(17) no
    C13 C18 . . 1.3907(18) no
    C14 C15 . . 1.4009(17) no
    C15 C16 . . 1.3746(18) no
    C16 C17 . . 1.398(2) no
    C17 C18 . . 1.377(2) no
    C10 H10A . . 0.9700 no
    C10 H10B . . 0.9700 no
    C12 H12 . . 0.9300 no
    C15 H15 . . 0.9300 no
    C16 H16 . . 0.9300 no
    C17 H17 . . 0.9300 no
    C18 H18 . . 0.9300 no
    C4 C5 . . 1.3843(18) no
    C5 C6 . . 1.3723(16) no
    C5 H5 . . 0.9300 no
    C7 H7A . . 0.9600 no
    C7 H7B . . 0.9600 no
    C7 H7C . . 0.9600 no
    C8 H8A . . 0.9600 no
    C8 H8B . . 0.9600 no
    C8 H8C . . 0.9600 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    O2 C12 3.3132(16) . 2_665 no
    O2 N4 3.1900(15) . 2_665 no
    O3 N4 3.2341(17) . 2_665 no
    O3 N1 2.6979(12) . . no
    O3 C12 3.3749(18) . 2_665 no
    O3 C4 3.2606(15) . 2_666 no
    O4 N2 2.8927(14) . . no
    O1 H10B 2.8800 . 2_666 no
    O2 H3 2.7700 . . no
    O2 H4 2.8800 . 2_665 no
    O3 H4 2.6800 . 2_665 no
    O4 H2A 2.0400 . . no
    O4 H10A 2.5900 . 2_675 no
    O4 H16 2.7500 . 2_575 no
    N1 O3 2.6979(12) . . no
    N2 O4 2.8927(14) . . no
    N3 N4 3.2184(17) . 1_556 no
    N4 O3 3.2341(17) . 2_665 no
    N4 N3 3.2184(17) . 1_554 no
    N4 O2 3.1900(15) . 2_665 no
    N1 H3 1.8800 . . no
    N3 H18 2.9500 . 1_556 no
    N3 H7C 2.5600 . . no
    N3 H4 2.4500 . 1_556 no
    N3 H7A 2.6700 . . no
    N4 H7A 2.8400 . 1_554 no
    C2 C4 3.5198(15) . 2_566 no
    C2 C5 3.5089(15) . 2_566 no
    C4 C9 3.5501(16) . 2_666 no
    C4 O3 3.2606(15) . 2_666 no
    C4 C2 3.5198(15) . 2_566 no
    C5 C2 3.5089(15) . 2_566 no
    C5 C9 3.5822(16) . 2_666 no
    C9 C15 3.5484(16) . . no
    C9 C4 3.5501(16) . 2_666 no
    C9 C5 3.5822(16) . 2_666 no
    C12 O3 3.3749(18) . 2_665 no
    C12 O2 3.3132(16) . 2_665 no
    C15 C9 3.5484(16) . . no
    C2 H3 2.8700 . . no
    C2 H4 3.0600 . 1_556 no
    C5 H8C 2.7400 . . no
    C5 H8A 2.7300 . . no
    C6 H3 2.7900 . . no
    C8 H5 2.5400 . . no
    C9 H2A 2.9000 . . no
    C12 H8B 3.0400 . 2_665 no
    C13 H7B 2.8900 . 2_566 no
    C14 H7B 2.7500 . 2_566 no
    C15 H5 2.8100 . 1_564 no
    C16 H5 2.8100 . 1_564 no
    H2A C9 2.9000 . . no
    H2A O4 2.0400 . . no
    H3 N1 1.8800 . . no
    H3 C2 2.8700 . . no
    H3 C6 2.7900 . . no
    H3 O2 2.7700 . . no
    H4 O3 2.6800 . 2_665 no
    H4 C2 3.0600 . 1_554 no
    H4 H7A 2.5500 . 1_554 no
    H4 N3 2.4500 . 1_554 no
    H4 O2 2.8800 . 2_665 no
    H5 C15 2.8100 . 1_546 no
    H5 C16 2.8100 . 1_546 no
    H5 C8 2.5400 . . no
    H5 H8A 2.3400 . . no
    H5 H8C 2.3200 . . no
    H7A N4 2.8400 . 1_556 no
    H7A N3 2.6700 . . no
    H7A H4 2.5500 . 1_556 no
    H7B C13 2.8900 . 2_566 no
    H7B C14 2.7500 . 2_566 no
    H7C N3 2.5600 . . no
    H8A H5 2.3400 . . no
    H8A C5 2.7300 . . no
    H8B C12 3.0400 . 2_665 no
    H8C H5 2.3200 . . no
    H8C C5 2.7400 . . no
    H10A O4 2.5900 . 2_675 no
    H10B O1 2.8800 . 2_666 no
    H16 O4 2.7500 . 2_575 no
    H18 N3 2.9500 . 1_554 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C9 O3 H3 . . . 109.00 no
    C4 O1 C7 . . . 118.24(12) no
    C6 O2 C8 . . . 117.57(11) no
    C12 N4 C13 . . . 109.14(12) no
    C12 N4 H4 . . . 125.00 no
    C13 N4 H4 . . . 125.00 no
    C2 N1 C6 . . . 116.09(9) no
    C2 N3 C4 . . . 115.07(11) no
    C2 N2 H2B . . . 120.00 no
    C2 N2 H2A . . . 120.00 no
    H2A N2 H2B . . . 120.00 no
    O3 C9 C10 . . . 113.48(11) no
    O4 C9 C10 . . . 123.11(12) no
    O3 C9 O4 . . . 123.41(11) no
    C9 C10 C11 . . . 111.17(10) no
    C12 C11 C14 . . . 106.25(11) no
    C10 C11 C14 . . . 126.02(11) no
    C10 C11 C12 . . . 127.64(11) no
    N4 C12 C11 . . . 110.41(12) no
    N4 C13 C14 . . . 107.17(10) no
    C14 C13 C18 . . . 122.00(12) no
    N4 C13 C18 . . . 130.78(13) no
    C11 C14 C13 . . . 107.03(10) no
    C11 C14 C15 . . . 133.95(11) no
    C13 C14 C15 . . . 118.96(10) no
    C14 C15 C16 . . . 118.84(12) no
    C15 C16 C17 . . . 121.25(13) no
    C16 C17 C18 . . . 121.46(13) no
    C13 C18 C17 . . . 117.48(13) no
    H10A C10 H10B . . . 108.00 no
    C11 C10 H10B . . . 109.00 no
    C11 C10 H10A . . . 109.00 no
    C9 C10 H10A . . . 109.00 no
    C9 C10 H10B . . . 109.00 no
    C11 C12 H12 . . . 125.00 no
    N4 C12 H12 . . . 125.00 no
    C16 C15 H15 . . . 121.00 no
    C14 C15 H15 . . . 121.00 no
    C17 C16 H16 . . . 119.00 no
    C15 C16 H16 . . . 119.00 no
    C18 C17 H17 . . . 119.00 no
    C16 C17 H17 . . . 119.00 no
    C13 C18 H18 . . . 121.00 no
    C17 C18 H18 . . . 121.00 no
    N1 C2 N2 . . . 117.23(9) no
    N1 C2 N3 . . . 126.02(11) no
    N2 C2 N3 . . . 116.74(11) no
    N3 C4 C5 . . . 124.42(10) no
    O1 C4 N3 . . . 119.52(12) no
    O1 C4 C5 . . . 116.06(12) no
    C4 C5 C6 . . . 115.35(11) no
    O2 C6 N1 . . . 111.97(10) no
    O2 C6 C5 . . . 124.99(12) no
    N1 C6 C5 . . . 123.04(11) no
    C4 C5 H5 . . . 122.00 no
    C6 C5 H5 . . . 122.00 no
    O1 C7 H7A . . . 109.00 no
    O1 C7 H7B . . . 109.00 no
    O1 C7 H7C . . . 109.00 no
    H7A C7 H7B . . . 109.00 no
    H7A C7 H7C . . . 109.00 no
    H7B C7 H7C . . . 110.00 no
    O2 C8 H8A . . . 110.00 no
    O2 C8 H8B . . . 109.00 no
    O2 C8 H8C . . . 109.00 no
    H8A C8 H8B . . . 109.00 no
    H8A C8 H8C . . . 109.00 no
    H8B C8 H8C . . . 109.00 no
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
    C7 O1 C4 C5 . . . . -176.42(11) no
    C7 O1 C4 N3 . . . . 3.89(17) no
    C8 O2 C6 N1 . . . . 175.18(11) no
    C8 O2 C6 C5 . . . . -5.60(17) no
    C13 N4 C12 C11 . . . . -0.47(15) no
    C12 N4 C13 C14 . . . . 0.36(14) no
    C12 N4 C13 C18 . . . . -177.05(13) no
    C6 N1 C2 N3 . . . . -0.22(15) no
    C2 N1 C6 O2 . . . . 179.64(9) no
    C6 N1 C2 N2 . . . . 179.42(10) no
    C2 N1 C6 C5 . . . . 0.40(16) no
    C2 N3 C4 C5 . . . . 1.29(16) no
    C4 N3 C2 N2 . . . . 179.77(10) no
    C2 N3 C4 O1 . . . . -179.05(10) no
    C4 N3 C2 N1 . . . . -0.59(15) no
    O4 C9 C10 C11 . . . . -109.62(14) no
    O3 C9 C10 C11 . . . . 70.10(13) no
    C9 C10 C11 C12 . . . . -109.00(14) no
    C9 C10 C11 C14 . . . . 66.91(16) no
    C14 C11 C12 N4 . . . . 0.37(14) no
    C10 C11 C12 N4 . . . . 176.92(11) no
    C10 C11 C14 C13 . . . . -176.77(11) no
    C10 C11 C14 C15 . . . . 0.2(2) no
    C12 C11 C14 C13 . . . . -0.14(13) no
    C12 C11 C14 C15 . . . . 176.84(13) no
    N4 C13 C14 C15 . . . . -177.65(10) no
    C18 C13 C14 C11 . . . . 177.55(11) no
    N4 C13 C14 C11 . . . . -0.13(13) no
    C18 C13 C14 C15 . . . . 0.03(17) no
    N4 C13 C18 C17 . . . . 176.85(13) no
    C14 C13 C18 C17 . . . . -0.23(19) no
    C13 C14 C15 C16 . . . . 0.16(16) no
    C11 C14 C15 C16 . . . . -176.54(12) no
    C14 C15 C16 C17 . . . . -0.16(19) no
    C15 C16 C17 C18 . . . . 0.0(2) no
    C16 C17 C18 C13 . . . . 0.2(2) no
    O1 C4 C5 C6 . . . . 179.20(10) no
    N3 C4 C5 C6 . . . . -1.13(17) no
    C4 C5 C6 O2 . . . . -178.92(11) no
    C4 C5 C6 N1 . . . . 0.21(17) no
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
    N2 H2A O4 . 0.86 2.04 2.8927(14) 171 yes
    O3 H3 N1 . 0.82 1.88 2.6979(12) 172 yes
    N4 H4 N3 1_554 0.86 2.45 3.2184(17) 149 yes
    C10 H10A O4 2_675 0.97 2.59 3.5491(18) 172 yes
