##############################################################################
###                                                                        ###
###        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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-03-16
_journal_date_accepted     2011-03-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      4
_journal_page_first     o943
_journal_page_last     o944
_journal_paper_category     QO
_journal_coeditor_code     HG5012
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 6775 '
_publ_section_title
;
3-(2-Hydroxyphenyl)-1-{(E)-[1-(pyrazin-2-yl)ethylidene]amino}thiourea
monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Erna Normaya' .
;
International Islamic University Malaysia (IIUM), PO Box 141, Kuantan, Malaysia
;
    'Yang Farina'
;
Additional correspondence author, e-mail: farina@ukm.my.
;
;
School of Chemical Sciences and Food Technology
Faculty Science and Technology
Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia
;
    'Siti Nadiah Abd Halim' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-(2-Hydroxyphenyl)-1-{(E)-[1-(pyrazin-2-yl)ethylidene]amino}thiourea
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H13 N5 O S, H2 O'
_chemical_formula_sum     'C13 H15 N5 O2 S'
_chemical_formula_iupac     'C13 H13 N5 O S, H2 O'
_chemical_formula_weight     305.36
_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     7.9808(5)
_cell_length_b     11.7557(8)
_cell_length_c     16.4160(11)
_cell_angle_alpha     99.6380(10)
_cell_angle_beta     94.1280(10)
_cell_angle_gamma     109.2000(10)
_cell_volume     1420.54(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6288
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     30.6
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.428
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     0.240
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.656
_exptl_absorpt_correction_T_max     0.746
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(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 APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18244
_diffrn_reflns_av_R_equivalents     0.031
_diffrn_reflns_av_sigmaI/netI     0.034
_diffrn_reflns_theta_min     1.3
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_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     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_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 >
2σ(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     6505
_reflns_number_gt     5267
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.046
_refine_ls_R_factor_gt     0.035
_refine_ls_wR_factor_gt     0.100
_refine_ls_wR_factor_ref     0.110
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.03
_refine_ls_number_reflns     6505
_refine_ls_number_parameters     411
_refine_ls_number_restraints     12
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0586P)²+0.4197P] 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     0.39
_refine_diff_density_min     -0.30
_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'
    'S' 'S' 0.1246 0.1234
                         '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 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and
Qmol (Gans & Shalloway, 2001)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    S S1 -0.09788(5) 0.17115(3) 0.34884(2) 0.02054(11) Uani d . 1 . .
    O O1 0.19179(14) 0.50524(9) 0.62276(6) 0.0191(2) Uani d D 1 . .
    H H1O 0.223(2) 0.5485(15) 0.6707(7) 0.029 Uiso d D 1 . .
    N N1 0.06763(16) 0.35848(11) 0.48035(7) 0.0160(3) Uani d D 1 . .
    H H1N 0.1553(18) 0.4298(10) 0.4942(10) 0.019 Uiso d D 1 . .
    N N2 0.17706(16) 0.37485(11) 0.35765(7) 0.0155(3) Uani d D 1 . .
    H H2N 0.176(2) 0.3458(15) 0.3051(6) 0.019 Uiso d D 1 . .
    N N3 0.30025(16) 0.48289(11) 0.40124(7) 0.0151(2) Uani d . 1 . .
    N N4 0.63006(17) 0.80104(11) 0.55376(8) 0.0187(3) Uani d . 1 . .
    N N5 0.65300(16) 0.74828(11) 0.38282(8) 0.0173(3) Uani d . 1 . .
    C C1 0.04480(19) 0.40506(13) 0.62335(9) 0.0157(3) Uani d . 1 . .
    C C2 -0.0340(2) 0.38248(14) 0.69423(9) 0.0193(3) Uani d . 1 . .
    H H2 0.0134 0.4390 0.7459 0.023 Uiso calc R 1 . .
    C C3 -0.1821(2) 0.27734(14) 0.68991(9) 0.0201(3) Uani d . 1 . .
    H H3 -0.2360 0.2619 0.7386 0.024 Uiso calc R 1 . .
    C C4 -0.2515(2) 0.19499(14) 0.61453(9) 0.0194(3) Uani d . 1 . .
    H H4 -0.3522 0.1228 0.6119 0.023 Uiso calc R 1 . .
    C C5 -0.17480(19) 0.21715(13) 0.54249(9) 0.0175(3) Uani d . 1 . .
    H H5 -0.2234 0.1606 0.4910 0.021 Uiso calc R 1 . .
    C C6 -0.02660(19) 0.32252(13) 0.54647(8) 0.0148(3) Uani d . 1 . .
    C C7 0.05216(19) 0.30635(13) 0.39999(9) 0.0153(3) Uani d . 1 . .
    C C8 0.42014(19) 0.55019(13) 0.36458(8) 0.0147(3) Uani d . 1 . .
    C C9 0.4445(2) 0.52302(14) 0.27451(8) 0.0187(3) Uani d . 1 . .
    H H9A 0.4149 0.4342 0.2557 0.028 Uiso calc R 1 . .
    H H9B 0.5692 0.5659 0.2680 0.028 Uiso calc R 1 . .
    H H9C 0.3653 0.5512 0.2410 0.028 Uiso calc R 1 . .
    C C10 0.53888(18) 0.66744(13) 0.41919(9) 0.0146(3) Uani d . 1 . .
    C C11 0.52873(19) 0.69459(13) 0.50503(9) 0.0167(3) Uani d . 1 . .
    H H11 0.4468 0.6349 0.5290 0.020 Uiso calc R 1 . .
    C C12 0.7435(2) 0.88265(14) 0.51665(9) 0.0201(3) Uani d . 1 . .
    H H12 0.8179 0.9601 0.5491 0.024 Uiso calc R 1 . .
    C C13 0.7538(2) 0.85604(14) 0.43227(10) 0.0210(3) Uani d . 1 . .
    H H13 0.8353 0.9162 0.4084 0.025 Uiso calc R 1 . .
    S S2 1.07562(5) 1.30651(3) 0.14135(2) 0.01929(10) Uani d . 1 . .
    O O2 0.78422(15) 0.96845(10) -0.13104(6) 0.0210(2) Uani d D 1 . .
    H H2O 0.746(2) 0.9237(16) -0.1782(7) 0.032 Uiso d D 1 . .
    N N6 0.91194(16) 1.11695(11) 0.01014(7) 0.0157(2) Uani d D 1 . .
    H H6N 0.8277(18) 1.0449(10) -0.0021(10) 0.019 Uiso d D 1 . .
    N N7 0.80922(16) 1.09918(11) 0.13407(7) 0.0157(3) Uani d D 1 . .
    H H7N 0.829(2) 1.1201(15) 0.1885(6) 0.019 Uiso d D 1 . .
    N N8 0.68925(16) 0.98922(10) 0.09106(7) 0.0150(2) Uani d . 1 . .
    N N9 0.35318(18) 0.67259(12) -0.06046(8) 0.0230(3) Uani d . 1 . .
    N N10 0.34629(17) 0.72072(12) 0.11192(8) 0.0194(3) Uani d . 1 . .
    C C14 0.92330(19) 1.07099(13) -0.13441(9) 0.0164(3) Uani d . 1 . .
    C C15 0.9944(2) 1.09597(14) -0.20668(9) 0.0201(3) Uani d . 1 . .
    H H15 0.9453 1.0394 -0.2581 0.024 Uiso calc R 1 . .
    C C16 1.1376(2) 1.20380(14) -0.20400(10) 0.0212(3) Uani d . 1 . .
    H H16 1.1856 1.2213 -0.2536 0.025 Uiso calc R 1 . .
    C C17 1.2101(2) 1.28569(14) -0.12866(10) 0.0212(3) Uani d . 1 . .
    H H17 1.3081 1.3591 -0.1271 0.025 Uiso calc R 1 . .
    C C18 1.1413(2) 1.26184(14) -0.05531(9) 0.0185(3) Uani d . 1 . .
    H H18 1.1926 1.3182 -0.0039 0.022 Uiso calc R 1 . .
    C C19 0.99712(19) 1.15496(13) -0.05791(8) 0.0154(3) Uani d . 1 . .
    C C20 0.93076(18) 1.16914(13) 0.09055(8) 0.0143(3) Uani d . 1 . .
    C C21 0.57203(19) 0.92136(13) 0.12853(9) 0.0157(3) Uani d . 1 . .
    C C22 0.5460(2) 0.94878(14) 0.21817(9) 0.0215(3) Uani d . 1 . .
    H H22A 0.5889 1.0380 0.2386 0.032 Uiso calc R 1 . .
    H H22B 0.6137 0.9122 0.2512 0.032 Uiso calc R 1 . .
    H H22C 0.4185 0.9141 0.2233 0.032 Uiso calc R 1 . .
    C C23 0.45390(19) 0.80368(13) 0.07433(9) 0.0158(3) Uani d . 1 . .
    C C24 0.4564(2) 0.77884(14) -0.01203(9) 0.0200(3) Uani d . 1 . .
    H H24 0.5342 0.8397 -0.0367 0.024 Uiso calc R 1 . .
    C C25 0.2466(2) 0.58978(14) -0.02229(10) 0.0238(3) Uani d . 1 . .
    H H25 0.1707 0.5126 -0.0547 0.029 Uiso calc R 1 . .
    C C26 0.2442(2) 0.61369(14) 0.06273(10) 0.0227(3) Uani d . 1 . .
    H H26 0.1674 0.5520 0.0872 0.027 Uiso calc R 1 . .
    O O1W 0.29296(15) 0.66684(11) 0.76876(7) 0.0240(3) Uani d D 1 . .
    H H1W 0.320(3) 0.6634(19) 0.8187(7) 0.036 Uiso d D 1 . .
    H H2W 0.209(2) 0.6932(18) 0.7662(11) 0.036 Uiso d D 1 . .
    O O2W 0.62751(16) 0.80846(11) 0.72836(7) 0.0264(3) Uani d D 1 . .
    H H4W 0.5218(15) 0.7672(16) 0.7342(11) 0.040 Uiso d D 1 . .
    H H3W 0.634(3) 0.8147(19) 0.6783(7) 0.040 Uiso d D 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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
    S1 C7 . 1.6797(14) ?
    O1 C1 . 1.3638(17) ?
    O1 H1O . 0.834(9) ?
    N1 C7 . 1.3370(18) ?
    N1 C6 . 1.4087(18) ?
    N1 H1N . 0.878(9) ?
    N2 N3 . 1.3656(16) ?
    N2 C7 . 1.3727(18) ?
    N2 H2N . 0.872(9) ?
    N3 C8 . 1.2837(18) ?
    N4 C11 . 1.3289(18) ?
    N4 C12 . 1.3471(19) ?
    N5 C10 . 1.3372(18) ?
    N5 C13 . 1.3425(19) ?
    C1 C2 . 1.385(2) ?
    C1 C6 . 1.4078(19) ?
    C2 C3 . 1.389(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.387(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.394(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.391(2) ?
    C5 H5 . 0.9500 ?
    C8 C10 . 1.4854(19) ?
    C8 C9 . 1.5000(19) ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 C11 . 1.4061(19) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.383(2) ?
    C12 H12 . 0.9500 ?
    C13 H13 . 0.9500 ?
    S2 C20 . 1.6799(14) ?
    O2 C14 . 1.3562(18) ?
    O2 H2O . 0.832(9) ?
    N6 C20 . 1.3347(17) ?
    N6 C19 . 1.4094(18) ?
    N6 H6N . 0.871(9) ?
    N7 N8 . 1.3671(16) ?
    N7 C20 . 1.3782(18) ?
    N7 H7N . 0.874(9) ?
    N8 C21 . 1.2830(18) ?
    N9 C24 . 1.3294(19) ?
    N9 C25 . 1.342(2) ?
    N10 C26 . 1.3379(19) ?
    N10 C23 . 1.3403(18) ?
    C14 C15 . 1.386(2) ?
    C14 C19 . 1.4122(19) ?
    C15 C16 . 1.392(2) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.387(2) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.392(2) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.389(2) ?
    C18 H18 . 0.9500 ?
    C21 C23 . 1.4844(19) ?
    C21 C22 . 1.4972(19) ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 C24 . 1.402(2) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.380(2) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
    O1W H1W . 0.845(9) ?
    O1W H2W . 0.829(9) ?
    O2W H4W . 0.845(9) ?
    O2W H3W . 0.842(9) ?
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
    C1 O1 H1O . . 109.1(13) ?
    C7 N1 C6 . . 133.34(12) ?
    C7 N1 H1N . . 112.4(11) ?
    C6 N1 H1N . . 114.2(11) ?
    N3 N2 C7 . . 117.93(11) ?
    N3 N2 H2N . . 123.7(11) ?
    C7 N2 H2N . . 118.4(11) ?
    C8 N3 N2 . . 120.36(12) ?
    C11 N4 C12 . . 116.55(13) ?
    C10 N5 C13 . . 116.46(13) ?
    O1 C1 C2 . . 123.55(13) ?
    O1 C1 C6 . . 116.29(12) ?
    C2 C1 C6 . . 120.16(13) ?
    C1 C2 C3 . . 120.07(14) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C4 C3 C2 . . 119.96(14) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 120.61(14) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C6 C5 C4 . . 119.63(13) ?
    C6 C5 H5 . . 120.2 ?
    C4 C5 H5 . . 120.2 ?
    C5 C6 C1 . . 119.56(13) ?
    C5 C6 N1 . . 127.05(13) ?
    C1 C6 N1 . . 113.39(12) ?
    N1 C7 N2 . . 113.40(12) ?
    N1 C7 S1 . . 127.44(11) ?
    N2 C7 S1 . . 119.15(10) ?
    N3 C8 C10 . . 114.04(12) ?
    N3 C8 C9 . . 126.55(13) ?
    C10 C8 C9 . . 119.37(12) ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    N5 C10 C11 . . 121.07(13) ?
    N5 C10 C8 . . 117.13(12) ?
    C11 C10 C8 . . 121.77(13) ?
    N4 C11 C10 . . 122.14(13) ?
    N4 C11 H11 . . 118.9 ?
    C10 C11 H11 . . 118.9 ?
    N4 C12 C13 . . 121.38(14) ?
    N4 C12 H12 . . 119.3 ?
    C13 C12 H12 . . 119.3 ?
    N5 C13 C12 . . 122.38(14) ?
    N5 C13 H13 . . 118.8 ?
    C12 C13 H13 . . 118.8 ?
    C14 O2 H2O . . 111.0(14) ?
    C20 N6 C19 . . 133.48(12) ?
    C20 N6 H6N . . 111.9(11) ?
    C19 N6 H6N . . 114.6(11) ?
    N8 N7 C20 . . 117.62(11) ?
    N8 N7 H7N . . 123.7(11) ?
    C20 N7 H7N . . 117.2(11) ?
    C21 N8 N7 . . 120.02(12) ?
    C24 N9 C25 . . 116.48(13) ?
    C26 N10 C23 . . 116.37(13) ?
    O2 C14 C15 . . 124.21(13) ?
    O2 C14 C19 . . 115.96(12) ?
    C15 C14 C19 . . 119.83(14) ?
    C14 C15 C16 . . 120.11(14) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C17 C16 C15 . . 119.82(14) ?
    C17 C16 H16 . . 120.1 ?
    C15 C16 H16 . . 120.1 ?
    C16 C17 C18 . . 120.92(15) ?
    C16 C17 H17 . . 119.5 ?
    C18 C17 H17 . . 119.5 ?
    C19 C18 C17 . . 119.41(14) ?
    C19 C18 H18 . . 120.3 ?
    C17 C18 H18 . . 120.3 ?
    C18 C19 N6 . . 126.65(13) ?
    C18 C19 C14 . . 119.91(13) ?
    N6 C19 C14 . . 113.44(12) ?
    N6 C20 N7 . . 113.11(12) ?
    N6 C20 S2 . . 128.34(11) ?
    N7 C20 S2 . . 118.52(10) ?
    N8 C21 C23 . . 113.87(12) ?
    N8 C21 C22 . . 127.09(13) ?
    C23 C21 C22 . . 119.03(12) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    N10 C23 C24 . . 121.20(13) ?
    N10 C23 C21 . . 116.94(12) ?
    C24 C23 C21 . . 121.86(13) ?
    N9 C24 C23 . . 121.95(14) ?
    N9 C24 H24 . . 119.0 ?
    C23 C24 H24 . . 119.0 ?
    N9 C25 C26 . . 121.75(14) ?
    N9 C25 H25 . . 119.1 ?
    C26 C25 H25 . . 119.1 ?
    N10 C26 C25 . . 122.24(14) ?
    N10 C26 H26 . . 118.9 ?
    C25 C26 H26 . . 118.9 ?
    H1W O1W H2W . . 109.0(16) ?
    H4W O2W H3W . . 110.5(16) ?
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 N2 N3 C8 . . . . 179.84(13) ?
    O1 C1 C2 C3 . . . . -179.12(13) ?
    C6 C1 C2 C3 . . . . 0.9(2) ?
    C1 C2 C3 C4 . . . . -0.1(2) ?
    C2 C3 C4 C5 . . . . -0.6(2) ?
    C3 C4 C5 C6 . . . . 0.4(2) ?
    C4 C5 C6 C1 . . . . 0.4(2) ?
    C4 C5 C6 N1 . . . . 179.51(14) ?
    O1 C1 C6 C5 . . . . 178.95(13) ?
    C2 C1 C6 C5 . . . . -1.1(2) ?
    O1 C1 C6 N1 . . . . -0.25(18) ?
    C2 C1 C6 N1 . . . . 179.70(13) ?
    C7 N1 C6 C5 . . . . -2.7(3) ?
    C7 N1 C6 C1 . . . . 176.41(15) ?
    C6 N1 C7 N2 . . . . -179.14(14) ?
    C6 N1 C7 S1 . . . . 0.5(2) ?
    N3 N2 C7 N1 . . . . 1.30(19) ?
    N3 N2 C7 S1 . . . . -178.38(10) ?
    N2 N3 C8 C10 . . . . 177.27(12) ?
    N2 N3 C8 C9 . . . . -0.6(2) ?
    C13 N5 C10 C11 . . . . -0.9(2) ?
    C13 N5 C10 C8 . . . . 177.13(13) ?
    N3 C8 C10 N5 . . . . -172.44(13) ?
    C9 C8 C10 N5 . . . . 5.6(2) ?
    N3 C8 C10 C11 . . . . 5.6(2) ?
    C9 C8 C10 C11 . . . . -176.37(13) ?
    C12 N4 C11 C10 . . . . 0.2(2) ?
    N5 C10 C11 N4 . . . . 0.4(2) ?
    C8 C10 C11 N4 . . . . -177.57(13) ?
    C11 N4 C12 C13 . . . . -0.3(2) ?
    C10 N5 C13 C12 . . . . 0.9(2) ?
    N4 C12 C13 N5 . . . . -0.2(2) ?
    C20 N7 N8 C21 . . . . -179.19(13) ?
    O2 C14 C15 C16 . . . . -179.93(14) ?
    C19 C14 C15 C16 . . . . -0.3(2) ?
    C14 C15 C16 C17 . . . . 0.6(2) ?
    C15 C16 C17 C18 . . . . -0.1(2) ?
    C16 C17 C18 C19 . . . . -0.6(2) ?
    C17 C18 C19 N6 . . . . 179.92(14) ?
    C17 C18 C19 C14 . . . . 0.8(2) ?
    C20 N6 C19 C18 . . . . 5.0(3) ?
    C20 N6 C19 C14 . . . . -175.84(15) ?
    O2 C14 C19 C18 . . . . 179.25(13) ?
    C15 C14 C19 C18 . . . . -0.4(2) ?
    O2 C14 C19 N6 . . . . 0.05(18) ?
    C15 C14 C19 N6 . . . . -179.61(13) ?
    C19 N6 C20 N7 . . . . 176.62(14) ?
    C19 N6 C20 S2 . . . . -1.4(2) ?
    N8 N7 C20 N6 . . . . 0.04(18) ?
    N8 N7 C20 S2 . . . . 178.23(10) ?
    N7 N8 C21 C23 . . . . -178.68(12) ?
    N7 N8 C21 C22 . . . . 0.9(2) ?
    C26 N10 C23 C24 . . . . 0.7(2) ?
    C26 N10 C23 C21 . . . . -178.17(13) ?
    N8 C21 C23 N10 . . . . 170.53(13) ?
    C22 C21 C23 N10 . . . . -9.1(2) ?
    N8 C21 C23 C24 . . . . -8.3(2) ?
    C22 C21 C23 C24 . . . . 172.12(14) ?
    C25 N9 C24 C23 . . . . -0.3(2) ?
    N10 C23 C24 N9 . . . . -0.1(2) ?
    C21 C23 C24 N9 . . . . 178.71(14) ?
    C24 N9 C25 C26 . . . . 0.0(2) ?
    C23 N10 C26 C25 . . . . -0.9(2) ?
    N9 C25 C26 N10 . . . . 0.6(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
    N1 H1n O1 . 0.878(13) 2.107(16) 2.5720(15) 112.3(12)
    N1 H1n N3 . 0.878(13) 2.038(15) 2.5435(18) 115.5(13)
    N6 H6n O2 . 0.871(12) 2.112(16) 2.5676(15) 111.9(12)
    N6 H6n N8 . 0.871(12) 2.023(15) 2.5358(17) 116.7(13)
    O1 H1o O1w . 0.833(12) 1.857(13) 2.6820(15) 170.3(16)
    O2 H2o O2w 1_554 0.833(13) 1.826(14) 2.6481(16) 168.9(17)
    O1w H1w N9 1_556 0.844(13) 1.962(12) 2.7958(17) 169(2)
    O1w H2w S2 2_676 0.827(18) 2.822(18) 3.4648(13) 136.0(16)
    O2w H3w N4 . 0.841(13) 2.021(12) 2.8547(17) 171(2)
    O2w H4w O1w . 0.845(15) 2.001(16) 2.8357(18) 169.1(16)
    N2 H2n S2 1_445 0.871(10) 2.667(10) 3.4802(12) 155.9(14)
    N7 H7n S1 1_665 0.874(10) 2.579(10) 3.4508(12) 175.6(15)
    C16 H16 N5 2_775 0.95 2.58 3.517(2) 172
    C22 H22a S1 1_665 0.98 2.79 3.4454(16) 125
