##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2002-09-10
_journal_date_accepted     2002-09-24
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2002
_journal_volume     58
_journal_issue     11
_journal_page_first     o675
_journal_page_last     o677
_journal_paper_category     FO
_publ_contact_author_name     'Professor Hoong-Kun Fun'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
_publ_contact_author_email     hkfun@usm.my
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6577888  Ext. 3690'
_publ_section_title
;
Hexamethylenetetraamine-4-nitrocatechol--water (1/2/1)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chantrapromma, Suchada'
;
Permanent address: Department of Chemistry
Faculty of Science
Prince of Songkla University
Hat-Yai
Songkhla 90112
Thailand
;
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Usman, Anwar' ?
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Fun, Hoong-Kun' ?
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Bo-Long Poh' ?
;
School of Chemistry
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Chatchanok Karalai' ?
;
Department of Chemistry
Faculty of Science
Prince of Songkla University
Hat-Yai
Songkhla 90112
Thailand
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Hexamethylenetetraamine--4-nitrocatechol--water (1/2/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H12 N4, 2C6 H5 N O4, H2 O'
_chemical_formula_sum     'C18 H24 N6 O9'
_chemical_formula_iupac     'C6 H12 N4, 2C6 H5 N O4, H2 O'
_chemical_formula_weight     468.43
_chemical_melting_point     418
_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     9.3520(5)
_cell_length_b     9.7671(5)
_cell_length_c     11.8264(6)
_cell_angle_alpha     99.4890(10)
_cell_angle_beta     107.5040(10)
_cell_angle_gamma     91.4410(10)
_cell_volume     1012.90(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4255
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     28.33
_cell_measurement_temperature     213(2)
_exptl_crystal_description     slab
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.536
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     492
_exptl_absorpt_coefficient_mu     0.125
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9564
_exptl_absorpt_correction_T_max     0.9852
_exptl_special_details
;
The data collection covered over a hemisphere of reciprocal space by a
combination of three sets of exposures; each set had a different φ angle (0,
88 and 180°) for the crystal and each exposure of 30s covered 0.3° in ω.
The crystal-to-detector distance was 5 cm and the detector swing angle was
-35°. Crystal decay was monitored by repeating fifty initial frames at the
end of data collection and analysing the intensity of duplicate reflections,
and was found to be negligible.
;
_diffrn_ambient_temperature     213(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     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     6443
_diffrn_reflns_av_R_equivalents     0.0107
_diffrn_reflns_av_sigmaI/netI     0.0200
_diffrn_reflns_theta_min     2.54
_diffrn_reflns_theta_max     28.27
_diffrn_reflns_theta_full     25.24
_diffrn_measured_fraction_theta_max     0.950
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     negligible
_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 > 2sigma(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     4761
_reflns_number_gt     4136
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0459
_refine_ls_R_factor_gt     0.0398
_refine_ls_wR_factor_gt     0.1033
_refine_ls_wR_factor_ref     0.1085
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_restrained_S_all     1.055
_refine_ls_number_reflns     4761
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0538P)²+0.3743P] 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     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.323
_refine_diff_density_min     -0.255
_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     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     SHELXTL
_computing_molecular_graphics     SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
loop_
    _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
    _atom_site_type_symbol
    O1W 0.23079(13) 0.33318(12) -0.48036(9) 0.0326(2) Uani d . 1 . . O
    H1W1 0.225(2) 0.284(2) -0.546(2) 0.050(6) Uiso d . 1 . . H
    H2W1 0.234(2) 0.416(3) -0.488(2) 0.057(6) Uiso d . 1 . . H
    O1 0.94592(11) -0.06689(10) 0.27346(8) 0.0274(2) Uani d . 1 . . O
    O2 0.73722(11) 0.04937(10) 0.10938(9) 0.0282(2) Uani d . 1 . . O
    O3 0.78786(13) -0.16362(12) -0.28514(9) 0.0374(3) Uani d . 1 . . O
    O4 0.95939(14) -0.30779(14) -0.24505(10) 0.0482(3) Uani d . 1 . . O
    N5 0.88144(13) -0.21923(13) -0.21274(10) 0.0284(3) Uani d . 1 . . N
    C7 0.93479(14) -0.10673(13) 0.15687(11) 0.0207(2) Uani d . 1 . . C
    C8 0.82533(14) -0.04660(12) 0.07293(11) 0.0199(2) Uani d . 1 . . C
    C9 0.80755(14) -0.08392(13) -0.04857(11) 0.0214(2) Uani d . 1 . . C
    C10 0.89935(14) -0.18008(13) -0.08535(11) 0.0220(3) Uani d . 1 . . C
    C11 1.00859(16) -0.23927(14) -0.00460(12) 0.0263(3) Uani d . 1 . . C
    C12 1.02541(15) -0.20146(14) 0.11656(12) 0.0256(3) Uani d . 1 . . C
    H9 0.7326(18) -0.0436(16) -0.1048(14) 0.025(4) Uiso d . 1 . . H
    H11 1.072(2) -0.3047(18) -0.0321(16) 0.034(4) Uiso d . 1 . . H
    H12 1.104(2) -0.2410(19) 0.1746(16) 0.038(5) Uiso d . 1 . . H
    H1O1 1.020(3) -0.109(2) 0.319(2) 0.066(7) Uiso d . 1 . . H
    H1O2 0.752(2) 0.067(2) 0.182(2) 0.048(6) Uiso d . 1 . . H
    O5 0.42071(12) 0.23909(11) -0.29887(9) 0.0303(2) Uani d . 1 . . O
    O6 0.58421(13) 0.16359(13) -0.09655(10) 0.0412(3) Uani d . 1 . . O
    O7 0.39757(14) 0.42170(13) 0.22498(9) 0.0411(3) Uani d . 1 . . O
    O8 0.22689(16) 0.54344(13) 0.13362(10) 0.0483(3) Uani d . 1 . . O
    N6 0.32171(14) 0.45981(12) 0.13294(10) 0.0283(3) Uani d . 1 . . N
    C13 0.39185(14) 0.29355(13) -0.19683(11) 0.0219(3) Uani d . 1 . . C
    C14 0.47885(15) 0.25479(14) -0.08872(12) 0.0246(3) Uani d . 1 . . C
    C15 0.45517(15) 0.30989(13) 0.01857(12) 0.0244(3) Uani d . 1 . . C
    C16 0.34505(15) 0.40230(13) 0.01912(11) 0.0230(3) Uani d . 1 . . C
    C17 0.25630(16) 0.44044(14) -0.08591(12) 0.0268(3) Uani d . 1 . . C
    C18 0.28084(15) 0.38568(14) -0.19332(11) 0.0251(3) Uani d . 1 . . C
    H15 0.514(2) 0.2855(18) 0.0898(16) 0.033(4) Uiso d . 1 . . H
    H17 0.179(2) 0.5017(18) -0.0854(15) 0.033(4) Uiso d . 1 . . H
    H18 0.2074(14) 0.4075(13) -0.2748(11) 0.007(3) Uiso d . 1 . . H
    H1O5 0.362(2) 0.272(2) -0.356(2) 0.054(6) Uiso d . 1 . . H
    H1O6 0.620(3) 0.142(2) -0.023(2) 0.064(7) Uiso d . 1 . . H
    N1 0.73343(12) 0.15535(11) 0.35028(9) 0.0232(2) Uani d . 1 . . N
    N2 0.73782(13) 0.37764(11) 0.48366(10) 0.0245(2) Uani d . 1 . . N
    N3 0.56506(12) 0.18079(12) 0.47543(10) 0.0245(2) Uani d . 1 . . N
    N4 0.83544(12) 0.17520(11) 0.56998(9) 0.0230(2) Uani d . 1 . . N
    C1 0.75276(16) 0.30868(14) 0.36732(12) 0.0252(3) Uani d . 1 . . C
    C2 0.58266(15) 0.11725(14) 0.35908(12) 0.0259(3) Uani d . 1 . . C
    C3 0.84761(15) 0.11075(15) 0.45086(11) 0.0246(3) Uani d . 1 . . C
    C4 0.58754(15) 0.33241(14) 0.48982(12) 0.0252(3) Uani d . 1 . . C
    C5 0.68169(15) 0.13499(15) 0.57239(12) 0.0257(3) Uani d . 1 . . C
    C6 0.85254(15) 0.32854(14) 0.58105(12) 0.0257(3) Uani d . 1 . . C
    H1A 0.6775(18) 0.3378(16) 0.3031(15) 0.026(4) Uiso d . 1 . . H
    H1B 0.851(2) 0.3373(18) 0.3649(16) 0.035(4) Uiso d . 1 . . H
    H2A 0.5692(18) 0.0153(18) 0.3495(15) 0.029(4) Uiso d . 1 . . H
    H2B 0.5055(19) 0.1504(17) 0.2933(15) 0.030(4) Uiso d . 1 . . H
    H3A 0.9453(19) 0.1379(16) 0.4483(14) 0.025(4) Uiso d . 1 . . H
    H3B 0.8324(18) 0.0119(18) 0.4436(15) 0.027(4) Uiso d . 1 . . H
    H4A 0.5776(18) 0.3737(16) 0.5677(15) 0.025(4) Uiso d . 1 . . H
    H4B 0.5111(18) 0.3621(16) 0.4242(14) 0.024(4) Uiso d . 1 . . H
    H5A 0.6674(19) 0.0310(19) 0.5617(15) 0.033(4) Uiso d . 1 . . H
    H5B 0.6708(19) 0.1787(17) 0.6503(15) 0.030(4) Uiso d . 1 . . H
    H6A 0.952(2) 0.3540(18) 0.5768(16) 0.033(4) Uiso d . 1 . . H
    H6B 0.8425(19) 0.3750(17) 0.6587(16) 0.030(4) Uiso d . 1 . . H
_geom_special_details
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds 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
    O1W H1W1 . 0.83(2) ?
    O1W H2W1 . 0.83(2) ?
    O1 C7 . 1.3409(15) ?
    O1 H1O1 . 0.90(2) ?
    O2 C8 . 1.3648(15) ?
    O2 H1O2 . 0.82(2) ?
    O3 N5 . 1.2331(16) ?
    O4 N5 . 1.2312(16) ?
    N5 C10 . 1.4488(16) ?
    C7 C12 . 1.3924(17) ?
    C7 C8 . 1.4105(16) ?
    C8 C9 . 1.3805(17) ?
    C9 C10 . 1.3925(17) ?
    C9 H9 . 0.954(16) ?
    C10 C11 . 1.3838(18) ?
    C11 C12 . 1.3788(18) ?
    C11 H11 . 0.968(18) ?
    C12 H12 . 0.977(18) ?
    O5 C13 . 1.3430(15) ?
    O5 H1O5 . 0.85(2) ?
    O6 C14 . 1.3582(16) ?
    O6 H1O6 . 0.90(2) ?
    O7 N6 . 1.2285(16) ?
    O8 N6 . 1.2216(16) ?
    N6 C16 . 1.4520(16) ?
    C13 C18 . 1.3963(18) ?
    C13 C14 . 1.4104(17) ?
    C14 C15 . 1.3779(18) ?
    C15 C16 . 1.3871(18) ?
    C15 H15 . 0.929(18) ?
    C16 C17 . 1.3851(18) ?
    C17 C18 . 1.3820(18) ?
    C17 H17 . 0.950(18) ?
    C18 H18 . 1.060(13) ?
    N1 C3 . 1.4748(15) yes
    N1 C1 . 1.4768(17) yes
    N1 C2 . 1.4873(17) yes
    N2 C6 . 1.4739(16) yes
    N2 C1 . 1.4768(16) yes
    N2 C4 . 1.4889(18) yes
    N3 C4 . 1.4648(17) yes
    N3 C5 . 1.4650(16) yes
    N3 C2 . 1.4715(17) yes
    N4 C6 . 1.4820(18) yes
    N4 C3 . 1.4837(16) yes
    N4 C5 . 1.4908(17) yes
    C1 H1A . 0.956(16) ?
    C1 H1B . 0.963(18) ?
    C2 H2A . 0.984(17) ?
    C2 H2B . 0.994(17) ?
    C3 H3A . 0.956(16) ?
    C3 H3B . 0.958(17) ?
    C4 H4A . 0.975(16) ?
    C4 H4B . 0.974(16) ?
    C5 H5A . 1.003(18) ?
    C5 H5B . 0.985(17) ?
    C6 H6A . 0.979(18) ?
    C6 H6B . 0.988(17) ?
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
    H1W1 O1W H2W1 . . 108(2) ?
    C7 O1 H1O1 . . 109.8(15) ?
    C8 O2 H1O2 . . 115.1(15) ?
    O4 N5 O3 . . 122.26(11) ?
    O4 N5 C10 . . 118.82(11) ?
    O3 N5 C10 . . 118.92(11) ?
    O1 C7 C12 . . 123.51(11) ?
    O1 C7 C8 . . 116.79(11) ?
    C12 C7 C8 . . 119.70(11) ?
    O2 C8 C9 . . 119.02(11) ?
    O2 C8 C7 . . 121.33(11) ?
    C9 C8 C7 . . 119.64(11) ?
    C8 C9 C10 . . 118.91(11) ?
    C8 C9 H9 . . 119.2(10) ?
    C10 C9 H9 . . 121.9(10) ?
    C11 C10 C9 . . 122.48(11) ?
    C11 C10 N5 . . 118.41(11) ?
    C9 C10 N5 . . 119.11(11) ?
    C12 C11 C10 . . 118.19(12) ?
    C12 C11 H11 . . 120.7(10) ?
    C10 C11 H11 . . 121.1(10) ?
    C11 C12 C7 . . 121.07(12) ?
    C11 C12 H12 . . 119.0(11) ?
    C7 C12 H12 . . 119.9(11) ?
    C13 O5 H1O5 . . 108.0(15) ?
    C14 O6 H1O6 . . 105.7(15) ?
    O8 N6 O7 . . 122.43(12) ?
    O8 N6 C16 . . 118.92(11) ?
    O7 N6 C16 . . 118.65(11) ?
    O5 C13 C18 . . 123.19(12) ?
    O5 C13 C14 . . 117.69(11) ?
    C18 C13 C14 . . 119.13(11) ?
    O6 C14 C15 . . 123.07(12) ?
    O6 C14 C13 . . 117.14(12) ?
    C15 C14 C13 . . 119.79(12) ?
    C14 C15 C16 . . 119.64(12) ?
    C14 C15 H15 . . 119.5(11) ?
    C16 C15 H15 . . 120.9(11) ?
    C17 C16 C15 . . 121.81(12) ?
    C17 C16 N6 . . 119.19(12) ?
    C15 C16 N6 . . 119.00(11) ?
    C18 C17 C16 . . 118.45(12) ?
    C18 C17 H17 . . 120.0(10) ?
    C16 C17 H17 . . 121.5(10) ?
    C17 C18 C13 . . 121.17(12) ?
    C17 C18 H18 . . 118.8(7) ?
    C13 C18 H18 . . 119.8(7) ?
    C3 N1 C1 . . 107.82(10) ?
    C3 N1 C2 . . 107.89(10) ?
    C1 N1 C2 . . 107.76(10) ?
    C6 N2 C1 . . 108.13(10) ?
    C6 N2 C4 . . 107.61(10) ?
    C1 N2 C4 . . 108.51(10) ?
    C4 N3 C5 . . 108.25(10) ?
    C4 N3 C2 . . 108.66(10) ?
    C5 N3 C2 . . 108.71(10) ?
    C6 N4 C3 . . 108.18(10) ?
    C6 N4 C5 . . 108.52(10) ?
    C3 N4 C5 . . 107.81(10) ?
    N2 C1 N1 . . 112.50(10) ?
    N2 C1 H1A . . 109.2(10) ?
    N1 C1 H1A . . 107.9(9) ?
    N2 C1 H1B . . 107.9(11) ?
    N1 C1 H1B . . 110.0(10) ?
    H1A C1 H1B . . 109.5(14) ?
    N3 C2 N1 . . 112.21(10) ?
    N3 C2 H2A . . 109.0(10) ?
    N1 C2 H2A . . 108.6(10) ?
    N3 C2 H2B . . 108.8(10) ?
    N1 C2 H2B . . 108.1(10) ?
    H2A C2 H2B . . 110.1(13) ?
    N1 C3 N4 . . 112.23(10) ?
    N1 C3 H3A . . 108.9(10) ?
    N4 C3 H3A . . 108.1(10) ?
    N1 C3 H3B . . 108.7(10) ?
    N4 C3 H3B . . 107.3(10) ?
    H3A C3 H3B . . 111.7(14) ?
    N3 C4 N2 . . 112.10(10) ?
    N3 C4 H4A . . 108.2(9) ?
    N2 C4 H4A . . 109.6(9) ?
    N3 C4 H4B . . 107.9(9) ?
    N2 C4 H4B . . 108.1(9) ?
    H4A C4 H4B . . 111.0(13) ?
    N3 C5 N4 . . 111.56(10) ?
    N3 C5 H5A . . 108.2(10) ?
    N4 C5 H5A . . 109.2(10) ?
    N3 C5 H5B . . 108.7(10) ?
    N4 C5 H5B . . 108.9(10) ?
    H5A C5 H5B . . 110.2(14) ?
    N2 C6 N4 . . 111.66(10) ?
    N2 C6 H6A . . 109.1(10) ?
    N4 C6 H6A . . 108.1(10) ?
    N2 C6 H6B . . 108.0(10) ?
    N4 C6 H6B . . 110.4(10) ?
    H6A C6 H6B . . 109.6(14) ?
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
    O1 C7 C8 O2 . . . . 1.16(18) ?
    C12 C7 C8 O2 . . . . -178.25(12) ?
    O1 C7 C8 C9 . . . . -179.59(12) ?
    C12 C7 C8 C9 . . . . 1.00(19) ?
    O2 C8 C9 C10 . . . . 178.92(12) ?
    C7 C8 C9 C10 . . . . -0.35(19) ?
    C8 C9 C10 C11 . . . . -0.4(2) ?
    C8 C9 C10 N5 . . . . -179.80(11) ?
    O4 N5 C10 C11 . . . . 3.0(2) ?
    O3 N5 C10 C11 . . . . -177.61(13) ?
    O4 N5 C10 C9 . . . . -177.57(13) ?
    O3 N5 C10 C9 . . . . 1.84(19) ?
    C9 C10 C11 C12 . . . . 0.4(2) ?
    N5 C10 C11 C12 . . . . 179.87(13) ?
    C10 C11 C12 C7 . . . . 0.2(2) ?
    O1 C7 C12 C11 . . . . 179.68(13) ?
    C8 C7 C12 C11 . . . . -0.9(2) ?
    O5 C13 C14 O6 . . . . -0.82(19) ?
    C18 C13 C14 O6 . . . . 179.17(13) ?
    O5 C13 C14 C15 . . . . 178.85(12) ?
    C18 C13 C14 C15 . . . . -1.2(2) ?
    O6 C14 C15 C16 . . . . -179.86(13) ?
    C13 C14 C15 C16 . . . . 0.5(2) ?
    C14 C15 C16 C17 . . . . 0.6(2) ?
    C14 C15 C16 N6 . . . . -179.82(12) ?
    O8 N6 C16 C17 . . . . -1.9(2) ?
    O7 N6 C16 C17 . . . . 177.59(13) ?
    O8 N6 C16 C15 . . . . 178.46(14) ?
    O7 N6 C16 C15 . . . . -2.03(19) ?
    C15 C16 C17 C18 . . . . -0.9(2) ?
    N6 C16 C17 C18 . . . . 179.46(12) ?
    C16 C17 C18 C13 . . . . 0.2(2) ?
    O5 C13 C18 C17 . . . . -179.22(13) ?
    C14 C13 C18 C17 . . . . 0.8(2) ?
    C6 N2 C1 N1 . . . . 58.95(14) ?
    C4 N2 C1 N1 . . . . -57.49(13) ?
    C3 N1 C1 N2 . . . . -58.39(14) ?
    C2 N1 C1 N2 . . . . 57.83(13) ?
    C4 N3 C2 N1 . . . . 58.87(13) ?
    C5 N3 C2 N1 . . . . -58.73(14) ?
    C3 N1 C2 N3 . . . . 57.82(13) ?
    C1 N1 C2 N3 . . . . -58.34(13) ?
    C1 N1 C3 N4 . . . . 58.02(14) ?
    C2 N1 C3 N4 . . . . -58.10(14) ?
    C6 N4 C3 N1 . . . . -58.45(14) ?
    C5 N4 C3 N1 . . . . 58.73(14) ?
    C5 N3 C4 N2 . . . . 59.89(13) ?
    C2 N3 C4 N2 . . . . -57.99(13) ?
    C6 N2 C4 N3 . . . . -59.51(13) ?
    C1 N2 C4 N3 . . . . 57.27(13) ?
    C4 N3 C5 N4 . . . . -58.82(13) ?
    C2 N3 C5 N4 . . . . 59.04(14) ?
    C6 N4 C5 N3 . . . . 58.17(13) ?
    C3 N4 C5 N3 . . . . -58.78(13) ?
    C1 N2 C6 N4 . . . . -58.66(14) ?
    C4 N2 C6 N4 . . . . 58.37(13) ?
    C3 N4 C6 N2 . . . . 58.51(14) ?
    C5 N4 C6 N2 . . . . -58.21(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O1W H1W1 O3 . . 2_654 0.83(2) 2.11(2) 2.940(2) 178(2) yes
    O1W H2W1 N2 . . 2_665 0.83(3) 2.02(3) 2.840(2) 172(2) yes
    O1 H1O1 N4 . . 2_756 0.90(2) 1.80(2) 2.684(2) 171(2) yes
    O2 H1O2 N1 . . 1_555 0.82(2) 2.09(2) 2.877(2) 161(2) yes
    O5 H1O5 O1W . . 1_555 0.85(2) 1.81(2) 2.654(2) 177(2) yes
    O6 H1O6 O2 . . 1_555 0.90(2) 1.99(2) 2.847(2) 160(2) yes
    C1 H1B O4 . . 2_755 0.96(2) 2.58(2) 3.417(2) 146(2) yes
    C2 H2A O5 . . 2_655 0.98(2) 2.47(2) 3.433(2) 166(2) yes
    C4 H4B O7 . . 1_555 0.97(2) 2.45(2) 3.370(2) 158(2) yes
    C9 H9 O6 . . 1_555 0.95(2) 2.49(2) 3.244(2) 136(2) yes
    C12 H12 O8 . . 1_645 0.98(2) 2.47(2) 3.158(2) 127(2) yes
    C18 H18 O1W . . 1_555 1.060(10)
                                  2.50(2) 3.235(2) 126.0(10)
                                                          yes
