#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229689
loop_
_publ_author_name
'Normaya, Erna'
'Farina, Yang'
'Halim, Siti Nadiah Abd'
'Tiekink, Edward R. T.'
_publ_section_title
;
 3-(2-Hydroxyphenyl)-1-{(E)-[1-(pyrazin-2-yl)ethylidene]amino}thiourea
 monohydrate
;
_journal_coeditor_code           HG5012
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o943
_journal_page_last               o944
_journal_paper_doi               10.1107/S1600536811010038
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H13 N5 O S, H2 O'
_chemical_formula_moiety         'C13 H13 N5 O S, H2 O'
_chemical_formula_sum            'C13 H15 N5 O2 S'
_chemical_formula_weight         305.36
_chemical_name_systematic
;
3-(2-Hydroxyphenyl)-1-{(E)-[1-(pyrazin-2-yl)ethylidene]amino}thiourea
monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.6380(10)
_cell_angle_beta                 94.1280(10)
_cell_angle_gamma                109.2000(10)
_cell_formula_units_Z            4
_cell_length_a                   7.9808(5)
_cell_length_b                   11.7557(8)
_cell_length_c                   16.4160(11)
_cell_measurement_reflns_used    6288
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.5
_cell_volume                     1420.54(16)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and
Qmol (Gans & Shalloway, 2001)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18244
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6505
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.4197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.110
_reflns_number_gt                5267
_reflns_number_total             6505
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5012.cif
_cod_data_source_block           I
_cod_database_code               2229689
_cod_database_fobs_code          2229689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . .
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'
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_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_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
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) ?
