3-(2-Hy-droxy-phen-yl)-1-{(E)-[1-(pyrazin-2-yl)ethyl-idene]amino}-thio-urea monohydrate.

In the title compound, C(13)H(13)N(5)OS·H(2)O, the thio-urea mol-ecules closely resemble each other and are approximately planar; the dihedral angles formed between the terminal benzene rings are 7.88 (8) and 7.20 (8)°, respectively. The observed planarity correlates with the presence of bifurcated N-H⋯(O,N) hydrogen bonds. In the crystal, the mol-ecules are connected into supra-molecular double chains via a combination of N-H⋯S (linking the two independent mol-ecules), O-H⋯O and O-H⋯N (linking dimeric aggregates into a supra-molecular chain via hy-droxy-water, water-water and water-pyrazine inter-actions) and O-H⋯S hydrogen bonds (connecting two chains). The chains are further connected by C-H⋯N and C-H⋯S inter-actions.

Related literature

For biological activity of thio­urea derivatives, see: Venkatachalam et al. (2004 ▶). For related structures, see: Gunasekaran et al. (2010 ▶); Dzulkifli et al. (2011 ▶). For additional geometric analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C13H13N5OS·H2O

M = 305.36

Triclinic,

a = 7.9808 (5) Å

b = 11.7557 (8) Å

c = 16.4160 (11) Å

α = 99.638 (1)°

β = 94.128 (1)°

γ = 109.200 (1)°

V = 1420.54 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.18 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.656, T max = 0.746

18244 measured reflections

6505 independent reflections

5267 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.110

S = 1.04

6505 reflections

411 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010038/hg5012sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010038/hg5012Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H13N5OS·H2O	Z = 4
Mr = 305.36	F(000) = 640
Triclinic, P1	Dx = 1.428 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9808 (5) Å	Cell parameters from 6288 reflections
b = 11.7557 (8) Å	θ = 2.5–30.6°
c = 16.4160 (11) Å	µ = 0.24 mm−1
α = 99.638 (1)°	T = 100 K
β = 94.128 (1)°	Block, yellow
γ = 109.200 (1)°	0.18 × 0.14 × 0.11 mm
V = 1420.54 (16) Å3

Bruker SMART APEX diffractometer	6505 independent reflections
Radiation source: fine-focus sealed tube	5267 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.656, Tmax = 0.746	k = −15→15
18244 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.4197P] where P = (Fo2 + 2Fc2)/3
6505 reflections	(Δ/σ)max = 0.001
411 parameters	Δρmax = 0.39 e Å−3
12 restraints	Δρmin = −0.30 e Å−3

Geometry. 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.

Refinement. 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.

	x	y	z	Uiso*/Ueq
S1	−0.09788 (5)	0.17115 (3)	0.34884 (2)	0.02054 (11)
O1	0.19179 (14)	0.50524 (9)	0.62276 (6)	0.0191 (2)
H1O	0.223 (2)	0.5485 (15)	0.6707 (7)	0.029*
N1	0.06763 (16)	0.35848 (11)	0.48035 (7)	0.0160 (3)
H1N	0.1553 (18)	0.4298 (10)	0.4942 (10)	0.019*
N2	0.17706 (16)	0.37485 (11)	0.35765 (7)	0.0155 (3)
H2N	0.176 (2)	0.3458 (15)	0.3051 (6)	0.019*
N3	0.30025 (16)	0.48289 (11)	0.40124 (7)	0.0151 (2)
N4	0.63006 (17)	0.80104 (11)	0.55376 (8)	0.0187 (3)
N5	0.65300 (16)	0.74828 (11)	0.38282 (8)	0.0173 (3)
C1	0.04480 (19)	0.40506 (13)	0.62335 (9)	0.0157 (3)
C2	−0.0340 (2)	0.38248 (14)	0.69423 (9)	0.0193 (3)
H2	0.0134	0.4390	0.7459	0.023*
C3	−0.1821 (2)	0.27734 (14)	0.68991 (9)	0.0201 (3)
H3	−0.2360	0.2619	0.7386	0.024*
C4	−0.2515 (2)	0.19499 (14)	0.61453 (9)	0.0194 (3)
H4	−0.3522	0.1228	0.6119	0.023*
C5	−0.17480 (19)	0.21715 (13)	0.54249 (9)	0.0175 (3)
H5	−0.2234	0.1606	0.4910	0.021*
C6	−0.02660 (19)	0.32252 (13)	0.54647 (8)	0.0148 (3)
C7	0.05216 (19)	0.30635 (13)	0.39999 (9)	0.0153 (3)
C8	0.42014 (19)	0.55019 (13)	0.36458 (8)	0.0147 (3)
C9	0.4445 (2)	0.52302 (14)	0.27451 (8)	0.0187 (3)
H9A	0.4149	0.4342	0.2557	0.028*
H9B	0.5692	0.5659	0.2680	0.028*
H9C	0.3653	0.5512	0.2410	0.028*
C10	0.53888 (18)	0.66744 (13)	0.41919 (9)	0.0146 (3)
C11	0.52873 (19)	0.69459 (13)	0.50503 (9)	0.0167 (3)
H11	0.4468	0.6349	0.5290	0.020*
C12	0.7435 (2)	0.88265 (14)	0.51665 (9)	0.0201 (3)
H12	0.8179	0.9601	0.5491	0.024*
C13	0.7538 (2)	0.85604 (14)	0.43227 (10)	0.0210 (3)
H13	0.8353	0.9162	0.4084	0.025*
S2	1.07562 (5)	1.30651 (3)	0.14135 (2)	0.01929 (10)
O2	0.78422 (15)	0.96845 (10)	−0.13104 (6)	0.0210 (2)
H2O	0.746 (2)	0.9237 (16)	−0.1782 (7)	0.032*
N6	0.91194 (16)	1.11695 (11)	0.01014 (7)	0.0157 (2)
H6N	0.8277 (18)	1.0449 (10)	−0.0021 (10)	0.019*
N7	0.80922 (16)	1.09918 (11)	0.13407 (7)	0.0157 (3)
H7N	0.829 (2)	1.1201 (15)	0.1885 (6)	0.019*
N8	0.68925 (16)	0.98922 (10)	0.09106 (7)	0.0150 (2)
N9	0.35318 (18)	0.67259 (12)	−0.06046 (8)	0.0230 (3)
N10	0.34629 (17)	0.72072 (12)	0.11192 (8)	0.0194 (3)
C14	0.92330 (19)	1.07099 (13)	−0.13441 (9)	0.0164 (3)
C15	0.9944 (2)	1.09597 (14)	−0.20668 (9)	0.0201 (3)
H15	0.9453	1.0394	−0.2581	0.024*
C16	1.1376 (2)	1.20380 (14)	−0.20400 (10)	0.0212 (3)
H16	1.1856	1.2213	−0.2536	0.025*
C17	1.2101 (2)	1.28569 (14)	−0.12866 (10)	0.0212 (3)
H17	1.3081	1.3591	−0.1271	0.025*
C18	1.1413 (2)	1.26184 (14)	−0.05531 (9)	0.0185 (3)
H18	1.1926	1.3182	−0.0039	0.022*
C19	0.99712 (19)	1.15496 (13)	−0.05791 (8)	0.0154 (3)
C20	0.93076 (18)	1.16914 (13)	0.09055 (8)	0.0143 (3)
C21	0.57203 (19)	0.92136 (13)	0.12853 (9)	0.0157 (3)
C22	0.5460 (2)	0.94878 (14)	0.21817 (9)	0.0215 (3)
H22A	0.5889	1.0380	0.2386	0.032*
H22B	0.6137	0.9122	0.2512	0.032*
H22C	0.4185	0.9141	0.2233	0.032*
C23	0.45390 (19)	0.80368 (13)	0.07433 (9)	0.0158 (3)
C24	0.4564 (2)	0.77884 (14)	−0.01203 (9)	0.0200 (3)
H24	0.5342	0.8397	−0.0367	0.024*
C25	0.2466 (2)	0.58978 (14)	−0.02229 (10)	0.0238 (3)
H25	0.1707	0.5126	−0.0547	0.029*
C26	0.2442 (2)	0.61369 (14)	0.06273 (10)	0.0227 (3)
H26	0.1674	0.5520	0.0872	0.027*
O1W	0.29296 (15)	0.66684 (11)	0.76876 (7)	0.0240 (3)
H1W	0.320 (3)	0.6634 (19)	0.8187 (7)	0.036*
H2W	0.209 (2)	0.6932 (18)	0.7662 (11)	0.036*
O2W	0.62751 (16)	0.80846 (11)	0.72836 (7)	0.0264 (3)
H4W	0.5218 (15)	0.7672 (16)	0.7342 (11)	0.040*
H3W	0.634 (3)	0.8147 (19)	0.6783 (7)	0.040*

	U11	U22	U33	U12	U13	U23
S1	0.0241 (2)	0.01728 (19)	0.01090 (18)	−0.00349 (15)	0.00142 (14)	−0.00018 (13)
O1	0.0207 (5)	0.0182 (5)	0.0111 (5)	−0.0003 (4)	0.0027 (4)	−0.0024 (4)
N1	0.0165 (6)	0.0149 (6)	0.0117 (6)	−0.0001 (5)	0.0033 (5)	0.0003 (5)
N2	0.0180 (6)	0.0140 (6)	0.0091 (5)	−0.0001 (5)	0.0020 (5)	−0.0006 (5)
N3	0.0156 (6)	0.0141 (6)	0.0125 (6)	0.0027 (5)	0.0002 (5)	0.0000 (5)
N4	0.0196 (6)	0.0176 (6)	0.0157 (6)	0.0040 (5)	−0.0003 (5)	0.0009 (5)
N5	0.0162 (6)	0.0180 (6)	0.0154 (6)	0.0026 (5)	0.0029 (5)	0.0038 (5)
C1	0.0171 (7)	0.0164 (7)	0.0136 (7)	0.0060 (5)	0.0022 (5)	0.0025 (5)
C2	0.0243 (8)	0.0221 (7)	0.0125 (7)	0.0089 (6)	0.0043 (6)	0.0033 (6)
C3	0.0241 (8)	0.0241 (8)	0.0159 (7)	0.0106 (6)	0.0090 (6)	0.0075 (6)
C4	0.0191 (7)	0.0189 (7)	0.0211 (7)	0.0054 (6)	0.0078 (6)	0.0064 (6)
C5	0.0181 (7)	0.0181 (7)	0.0144 (7)	0.0050 (6)	0.0022 (5)	0.0006 (6)
C6	0.0175 (7)	0.0168 (7)	0.0113 (6)	0.0070 (6)	0.0043 (5)	0.0033 (5)
C7	0.0161 (7)	0.0162 (7)	0.0127 (7)	0.0047 (5)	0.0012 (5)	0.0025 (5)
C8	0.0165 (7)	0.0154 (7)	0.0113 (6)	0.0049 (5)	0.0013 (5)	0.0019 (5)
C9	0.0213 (7)	0.0202 (7)	0.0112 (7)	0.0034 (6)	0.0034 (6)	0.0017 (6)
C10	0.0138 (7)	0.0158 (7)	0.0140 (7)	0.0048 (5)	0.0017 (5)	0.0033 (5)
C11	0.0189 (7)	0.0157 (7)	0.0133 (7)	0.0035 (6)	0.0007 (5)	0.0027 (5)
C12	0.0202 (7)	0.0152 (7)	0.0200 (7)	0.0015 (6)	0.0000 (6)	0.0010 (6)
C13	0.0192 (7)	0.0184 (7)	0.0211 (8)	0.0008 (6)	0.0017 (6)	0.0046 (6)
S2	0.0241 (2)	0.01506 (18)	0.01128 (18)	−0.00166 (14)	0.00061 (14)	0.00055 (13)
O2	0.0234 (6)	0.0209 (5)	0.0113 (5)	0.0005 (4)	0.0013 (4)	−0.0016 (4)
N6	0.0174 (6)	0.0131 (6)	0.0116 (6)	−0.0005 (5)	0.0031 (5)	0.0001 (5)
N7	0.0198 (6)	0.0135 (6)	0.0093 (5)	0.0010 (5)	0.0018 (5)	−0.0003 (5)
N8	0.0170 (6)	0.0118 (6)	0.0135 (6)	0.0026 (5)	0.0008 (5)	0.0004 (4)
N9	0.0229 (7)	0.0214 (7)	0.0180 (6)	0.0018 (5)	0.0023 (5)	−0.0022 (5)
N10	0.0179 (6)	0.0185 (6)	0.0187 (6)	0.0013 (5)	0.0022 (5)	0.0057 (5)
C14	0.0183 (7)	0.0169 (7)	0.0150 (7)	0.0073 (6)	0.0030 (5)	0.0029 (6)
C15	0.0251 (8)	0.0255 (8)	0.0117 (7)	0.0116 (6)	0.0033 (6)	0.0032 (6)
C16	0.0264 (8)	0.0259 (8)	0.0181 (7)	0.0138 (7)	0.0106 (6)	0.0097 (6)
C17	0.0223 (8)	0.0212 (7)	0.0225 (8)	0.0076 (6)	0.0088 (6)	0.0079 (6)
C18	0.0196 (7)	0.0189 (7)	0.0167 (7)	0.0057 (6)	0.0052 (6)	0.0034 (6)
C19	0.0187 (7)	0.0182 (7)	0.0110 (6)	0.0079 (6)	0.0037 (5)	0.0035 (5)
C20	0.0158 (7)	0.0146 (6)	0.0114 (6)	0.0042 (5)	0.0015 (5)	0.0021 (5)
C21	0.0173 (7)	0.0167 (7)	0.0127 (7)	0.0054 (6)	0.0019 (5)	0.0029 (5)
C22	0.0231 (8)	0.0217 (8)	0.0136 (7)	0.0011 (6)	0.0044 (6)	0.0003 (6)
C23	0.0150 (7)	0.0160 (7)	0.0153 (7)	0.0040 (5)	0.0018 (5)	0.0027 (5)
C24	0.0202 (7)	0.0194 (7)	0.0154 (7)	0.0015 (6)	0.0021 (6)	0.0006 (6)
C25	0.0215 (8)	0.0166 (7)	0.0264 (8)	0.0008 (6)	0.0015 (6)	−0.0016 (6)
C26	0.0194 (7)	0.0188 (7)	0.0248 (8)	−0.0001 (6)	0.0017 (6)	0.0055 (6)
O1W	0.0261 (6)	0.0278 (6)	0.0161 (5)	0.0115 (5)	−0.0008 (5)	−0.0039 (5)
O2W	0.0304 (6)	0.0284 (6)	0.0128 (5)	0.0032 (5)	0.0014 (5)	−0.0014 (5)

S1—C7	1.6797 (14)	O2—H2O	0.832 (9)
O1—C1	1.3638 (17)	N6—C20	1.3347 (17)
O1—H1O	0.834 (9)	N6—C19	1.4094 (18)
N1—C7	1.3370 (18)	N6—H6N	0.871 (9)
N1—C6	1.4087 (18)	N7—N8	1.3671 (16)
N1—H1N	0.878 (9)	N7—C20	1.3782 (18)
N2—N3	1.3656 (16)	N7—H7N	0.874 (9)
N2—C7	1.3727 (18)	N8—C21	1.2830 (18)
N2—H2N	0.872 (9)	N9—C24	1.3294 (19)
N3—C8	1.2837 (18)	N9—C25	1.342 (2)
N4—C11	1.3289 (18)	N10—C26	1.3379 (19)
N4—C12	1.3471 (19)	N10—C23	1.3403 (18)
N5—C10	1.3372 (18)	C14—C15	1.386 (2)
N5—C13	1.3425 (19)	C14—C19	1.4122 (19)
C1—C2	1.385 (2)	C15—C16	1.392 (2)
C1—C6	1.4078 (19)	C15—H15	0.9500
C2—C3	1.389 (2)	C16—C17	1.387 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.387 (2)	C17—C18	1.392 (2)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.394 (2)	C18—C19	1.389 (2)
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.391 (2)	C21—C23	1.4844 (19)
C5—H5	0.9500	C21—C22	1.4972 (19)
C8—C10	1.4854 (19)	C22—H22A	0.9800
C8—C9	1.5000 (19)	C22—H22B	0.9800
C9—H9A	0.9800	C22—H22C	0.9800
C9—H9B	0.9800	C23—C24	1.402 (2)
C9—H9C	0.9800	C24—H24	0.9500
C10—C11	1.4061 (19)	C25—C26	1.380 (2)
C11—H11	0.9500	C25—H25	0.9500
C12—C13	1.383 (2)	C26—H26	0.9500
C12—H12	0.9500	O1W—H1W	0.845 (9)
C13—H13	0.9500	O1W—H2W	0.829 (9)
S2—C20	1.6799 (14)	O2W—H4W	0.845 (9)
O2—C14	1.3562 (18)	O2W—H3W	0.842 (9)
C1—O1—H1O	109.1 (13)	C20—N6—C19	133.48 (12)
C7—N1—C6	133.34 (12)	C20—N6—H6N	111.9 (11)
C7—N1—H1N	112.4 (11)	C19—N6—H6N	114.6 (11)
C6—N1—H1N	114.2 (11)	N8—N7—C20	117.62 (11)
N3—N2—C7	117.93 (11)	N8—N7—H7N	123.7 (11)
N3—N2—H2N	123.7 (11)	C20—N7—H7N	117.2 (11)
C7—N2—H2N	118.4 (11)	C21—N8—N7	120.02 (12)
C8—N3—N2	120.36 (12)	C24—N9—C25	116.48 (13)
C11—N4—C12	116.55 (13)	C26—N10—C23	116.37 (13)
C10—N5—C13	116.46 (13)	O2—C14—C15	124.21 (13)
O1—C1—C2	123.55 (13)	O2—C14—C19	115.96 (12)
O1—C1—C6	116.29 (12)	C15—C14—C19	119.83 (14)
C2—C1—C6	120.16 (13)	C14—C15—C16	120.11 (14)
C1—C2—C3	120.07 (14)	C14—C15—H15	119.9
C1—C2—H2	120.0	C16—C15—H15	119.9
C3—C2—H2	120.0	C17—C16—C15	119.82 (14)
C4—C3—C2	119.96 (14)	C17—C16—H16	120.1
C4—C3—H3	120.0	C15—C16—H16	120.1
C2—C3—H3	120.0	C16—C17—C18	120.92 (15)
C3—C4—C5	120.61 (14)	C16—C17—H17	119.5
C3—C4—H4	119.7	C18—C17—H17	119.5
C5—C4—H4	119.7	C19—C18—C17	119.41 (14)
C6—C5—C4	119.63 (13)	C19—C18—H18	120.3
C6—C5—H5	120.2	C17—C18—H18	120.3
C4—C5—H5	120.2	C18—C19—N6	126.65 (13)
C5—C6—C1	119.56 (13)	C18—C19—C14	119.91 (13)
C5—C6—N1	127.05 (13)	N6—C19—C14	113.44 (12)
C1—C6—N1	113.39 (12)	N6—C20—N7	113.11 (12)
N1—C7—N2	113.40 (12)	N6—C20—S2	128.34 (11)
N1—C7—S1	127.44 (11)	N7—C20—S2	118.52 (10)
N2—C7—S1	119.15 (10)	N8—C21—C23	113.87 (12)
N3—C8—C10	114.04 (12)	N8—C21—C22	127.09 (13)
N3—C8—C9	126.55 (13)	C23—C21—C22	119.03 (12)
C10—C8—C9	119.37 (12)	C21—C22—H22A	109.5
C8—C9—H9A	109.5	C21—C22—H22B	109.5
C8—C9—H9B	109.5	H22A—C22—H22B	109.5
H9A—C9—H9B	109.5	C21—C22—H22C	109.5
C8—C9—H9C	109.5	H22A—C22—H22C	109.5
H9A—C9—H9C	109.5	H22B—C22—H22C	109.5
H9B—C9—H9C	109.5	N10—C23—C24	121.20 (13)
N5—C10—C11	121.07 (13)	N10—C23—C21	116.94 (12)
N5—C10—C8	117.13 (12)	C24—C23—C21	121.86 (13)
C11—C10—C8	121.77 (13)	N9—C24—C23	121.95 (14)
N4—C11—C10	122.14 (13)	N9—C24—H24	119.0
N4—C11—H11	118.9	C23—C24—H24	119.0
C10—C11—H11	118.9	N9—C25—C26	121.75 (14)
N4—C12—C13	121.38 (14)	N9—C25—H25	119.1
N4—C12—H12	119.3	C26—C25—H25	119.1
C13—C12—H12	119.3	N10—C26—C25	122.24 (14)
N5—C13—C12	122.38 (14)	N10—C26—H26	118.9
N5—C13—H13	118.8	C25—C26—H26	118.9
C12—C13—H13	118.8	H1W—O1W—H2W	109.0 (16)
C14—O2—H2O	111.0 (14)	H4W—O2W—H3W	110.5 (16)
C7—N2—N3—C8	179.84 (13)	C20—N7—N8—C21	−179.19 (13)
O1—C1—C2—C3	−179.12 (13)	O2—C14—C15—C16	−179.93 (14)
C6—C1—C2—C3	0.9 (2)	C19—C14—C15—C16	−0.3 (2)
C1—C2—C3—C4	−0.1 (2)	C14—C15—C16—C17	0.6 (2)
C2—C3—C4—C5	−0.6 (2)	C15—C16—C17—C18	−0.1 (2)
C3—C4—C5—C6	0.4 (2)	C16—C17—C18—C19	−0.6 (2)
C4—C5—C6—C1	0.4 (2)	C17—C18—C19—N6	179.92 (14)
C4—C5—C6—N1	179.51 (14)	C17—C18—C19—C14	0.8 (2)
O1—C1—C6—C5	178.95 (13)	C20—N6—C19—C18	5.0 (3)
C2—C1—C6—C5	−1.1 (2)	C20—N6—C19—C14	−175.84 (15)
O1—C1—C6—N1	−0.25 (18)	O2—C14—C19—C18	179.25 (13)
C2—C1—C6—N1	179.70 (13)	C15—C14—C19—C18	−0.4 (2)
C7—N1—C6—C5	−2.7 (3)	O2—C14—C19—N6	0.05 (18)
C7—N1—C6—C1	176.41 (15)	C15—C14—C19—N6	−179.61 (13)
C6—N1—C7—N2	−179.14 (14)	C19—N6—C20—N7	176.62 (14)
C6—N1—C7—S1	0.5 (2)	C19—N6—C20—S2	−1.4 (2)
N3—N2—C7—N1	1.30 (19)	N8—N7—C20—N6	0.04 (18)
N3—N2—C7—S1	−178.38 (10)	N8—N7—C20—S2	178.23 (10)
N2—N3—C8—C10	177.27 (12)	N7—N8—C21—C23	−178.68 (12)
N2—N3—C8—C9	−0.6 (2)	N7—N8—C21—C22	0.9 (2)
C13—N5—C10—C11	−0.9 (2)	C26—N10—C23—C24	0.7 (2)
C13—N5—C10—C8	177.13 (13)	C26—N10—C23—C21	−178.17 (13)
N3—C8—C10—N5	−172.44 (13)	N8—C21—C23—N10	170.53 (13)
C9—C8—C10—N5	5.6 (2)	C22—C21—C23—N10	−9.1 (2)
N3—C8—C10—C11	5.6 (2)	N8—C21—C23—C24	−8.3 (2)
C9—C8—C10—C11	−176.37 (13)	C22—C21—C23—C24	172.12 (14)
C12—N4—C11—C10	0.2 (2)	C25—N9—C24—C23	−0.3 (2)
N5—C10—C11—N4	0.4 (2)	N10—C23—C24—N9	−0.1 (2)
C8—C10—C11—N4	−177.57 (13)	C21—C23—C24—N9	178.71 (14)
C11—N4—C12—C13	−0.3 (2)	C24—N9—C25—C26	0.0 (2)
C10—N5—C13—C12	0.9 (2)	C23—N10—C26—C25	−0.9 (2)
N4—C12—C13—N5	−0.2 (2)	N9—C25—C26—N10	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
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···O2wi	0.833 (13)	1.826 (14)	2.6481 (16)	168.9 (17)
O1w—H1w···N9ii	0.844 (13)	1.962 (12)	2.7958 (17)	169 (2)
O1w—H2w···S2iii	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···S2iv	0.871 (10)	2.667 (10)	3.4802 (12)	155.9 (14)
N7—H7n···S1v	0.874 (10)	2.579 (10)	3.4508 (12)	175.6 (15)
C16—H16···N5vi	0.95	2.58	3.517 (2)	172
C22—H22a···S1v	0.98	2.79	3.4454 (16)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1	0.88 (1)	2.11 (2)	2.5720 (15)	112 (1)
N1—H1n⋯N3	0.88 (1)	2.04 (2)	2.5435 (18)	116 (1)
N6—H6n⋯O2	0.87 (1)	2.11 (2)	2.5676 (15)	112 (1)
N6—H6n⋯N8	0.87 (1)	2.02 (2)	2.5358 (17)	117 (1)
O1—H1o⋯O1w	0.83 (1)	1.86 (1)	2.6820 (15)	170 (2)
O2—H2o⋯O2wi	0.83 (1)	1.83 (1)	2.6481 (16)	169 (2)
O1w—H1w⋯N9ii	0.84 (1)	1.96 (1)	2.7958 (17)	169 (2)
O1w—H2w⋯S2iii	0.83 (2)	2.82 (2)	3.4648 (13)	136 (2)
O2w—H3w⋯N4	0.84 (1)	2.02 (1)	2.8547 (17)	171 (2)
O2w—H4w⋯O1w	0.85 (2)	2.00 (2)	2.8357 (18)	169 (2)
N2—H2n⋯S2iv	0.87 (1)	2.67 (1)	3.4802 (12)	156 (1)
N7—H7n⋯S1v	0.87 (1)	2.58 (1)	3.4508 (12)	176 (2)
C16—H16⋯N5vi	0.95	2.58	3.517 (2)	172
C22—H22a⋯S1v	0.98	2.79	3.4454 (16)	125

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .