Chlorido[(E)-2-hydr-oxy-6-(isonicotinoyl-hydrazonometh-yl)phen-yl]mercury(II) monohydrate.

The asymmetric unit of the title compound, [Hg(C(13)H(10)N(3)O(2))Cl]·H(2)O, contains two independent mercury(II) complexes with slightly different conformations, related via a pseudo-inversion centre, and two water mol-ecules. The Hg(II) atoms show a typical linear geometry to a C atom of the benzene ring and to a Cl atom. A benzene C and the azomethine N atom chelate the Hg(II) atoms with weak intra-molecular Hg⋯N bonding distances of 2.735 (3) and 2.739 (3) Å, respectively. The resulting five-membered metallacycles are nearly coplanar with the benzene rings [dihedral angles = 0.9 (1) and 0.7 (1)°], while the pyridine rings make dihedral angles with the benzene units of 58.17 (1) and 56.58 (1)°. In the crystal structure, the Hg(II) complexes are linked by hydr-oxy donor and pyridine acceptor groups into chains along [010]. The water mol-ecules connect the complexes through inter-molecular O-H⋯O(carbon-yl) bonds in the a-axis direction, and the azomethine H atoms donate towards the water O atoms, forming a three-dimensional network of inter-molecular O-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For general background, see: Gruter et al. (1995 ▶); Soro et al. (2005 ▶); Xu et al. (2009b ▶). For related structures, see: Hao et al. (2007 ▶); Lin et al. (2002 ▶); For the synthesis of related cyclomercurated compounds, see: Xu et al. (2009a ▶).

Experimental

Crystal data

[Hg(C13H10N3O2)Cl]·H2O

M = 494.30

Monoclinic,

a = 14.5932 (16) Å

b = 14.0111 (15) Å

c = 15.3711 (17) Å

β = 104.6850 (10)°

V = 3040.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 10.31 mm−1

T = 296 K

0.37 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.113, T max = 0.179 (expected range = 0.048–0.076)

22798 measured reflections

5658 independent reflections

4683 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.046

S = 1.05

5658 reflections

381 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.83 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023824/si2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023824/si2184Isup2.hkl

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

[Hg(C13H10N3O2)Cl]·H2O	F(000) = 1856
Mr = 494.30	Dx = 2.160 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.5932 (16) Å	Cell parameters from 5064 reflections
b = 14.0111 (15) Å	θ = 2.7–28.3°
c = 15.3711 (17) Å	µ = 10.31 mm−1
β = 104.685 (1)°	T = 296 K
V = 3040.2 (6) Å3	Block, colorless
Z = 8	0.37 × 0.28 × 0.25 mm

Bruker SMART APEX CCD area-detector diffractometer	5658 independent reflections
Radiation source: fine-focus sealed tube	4683 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.113, Tmax = 0.179	k = −16→16
22798 measured reflections	l = −16→18

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0197P)2 + 1.3364P] where P = (Fo2 + 2Fc2)/3
5658 reflections	(Δ/σ)max = 0.002
381 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.83 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)are estimated using the full covariance matrix. The cell e.s.d.'s are takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused when they are defined by crystal symmetry. An approximate (isotropic)treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
Hg1	0.909422 (9)	0.795528 (10)	0.140566 (10)	0.03271 (5)
Hg2	0.088755 (10)	0.667392 (10)	0.363229 (10)	0.03354 (5)
Cl1	1.06292 (6)	0.74039 (8)	0.15848 (7)	0.0482 (3)
Cl2	−0.06489 (7)	0.72341 (8)	0.34424 (7)	0.0485 (3)
O1	0.85291 (17)	1.00819 (18)	0.13735 (19)	0.0444 (7)
H1	0.8409	1.0641	0.1231	0.067*
O2	0.91602 (18)	0.54581 (19)	0.0795 (2)	0.0539 (8)
O3	0.14451 (18)	0.45504 (17)	0.3573 (2)	0.0473 (7)
H3	0.1565	0.3987	0.3693	0.071*
O4	0.08053 (18)	0.91980 (18)	0.4187 (2)	0.0494 (7)
N1	0.7764 (2)	0.6537 (2)	0.1123 (2)	0.0339 (7)
N2	0.7733 (2)	0.55515 (19)	0.11402 (19)	0.0338 (7)
H2D	0.7253	0.5255	0.1239	0.041*
N3	0.8374 (2)	0.2013 (2)	0.1131 (2)	0.0397 (8)
N4	0.2225 (2)	0.8089 (2)	0.3911 (2)	0.0362 (7)
N5	0.2266 (2)	0.9077 (2)	0.39086 (19)	0.0352 (7)
H5D	0.2760	0.9368	0.3836	0.042*
N6	0.1645 (2)	1.2624 (2)	0.3851 (2)	0.0397 (8)
C1	0.7779 (2)	0.8579 (2)	0.1197 (2)	0.0279 (8)
C2	0.7707 (3)	0.9568 (3)	0.1195 (2)	0.0349 (8)
C3	0.6823 (3)	1.0005 (3)	0.1066 (3)	0.0431 (10)
H3A	0.6779	1.0667	0.1076	0.052*
C4	0.6011 (3)	0.9454 (3)	0.0924 (3)	0.0495 (11)
H4	0.5422	0.9746	0.0830	0.059*
C5	0.6075 (3)	0.8465 (3)	0.0920 (3)	0.0411 (9)
H5	0.5528	0.8097	0.0830	0.049*
C6	0.6953 (2)	0.8023 (2)	0.1051 (2)	0.0313 (8)
C7	0.6986 (3)	0.6972 (2)	0.1046 (2)	0.0331 (8)
H7	0.6430	0.6625	0.0986	0.040*
C8	0.8484 (3)	0.5069 (2)	0.0996 (2)	0.0351 (9)
C9	0.8433 (2)	0.4003 (2)	0.1063 (2)	0.0302 (8)
C10	0.8804 (2)	0.3447 (2)	0.0486 (3)	0.0361 (9)
H10	0.9089	0.3731	0.0075	0.043*
C11	0.8744 (2)	0.2467 (3)	0.0532 (3)	0.0379 (9)
H11	0.8973	0.2102	0.0127	0.046*
C12	0.8025 (3)	0.2558 (3)	0.1688 (3)	0.0416 (9)
H12	0.7760	0.2254	0.2104	0.050*
C13	0.8035 (3)	0.3542 (3)	0.1680 (3)	0.0393 (9)
H13	0.7782	0.3890	0.2079	0.047*
C14	0.2197 (2)	0.6052 (2)	0.3792 (2)	0.0291 (8)
C15	0.3026 (3)	0.6602 (2)	0.3951 (2)	0.0324 (8)
C16	0.3903 (3)	0.6153 (3)	0.4047 (3)	0.0446 (10)
H16	0.4453	0.6518	0.4149	0.054*
C17	0.3955 (3)	0.5171 (3)	0.3992 (3)	0.0510 (11)
H17	0.4540	0.4876	0.4057	0.061*
C18	0.3143 (3)	0.4625 (3)	0.3840 (3)	0.0447 (10)
H18	0.3180	0.3965	0.3798	0.054*
C19	0.2271 (3)	0.5063 (3)	0.3751 (2)	0.0350 (9)
C20	0.3007 (3)	0.7648 (3)	0.3986 (2)	0.0361 (9)
H20	0.3568	0.7992	0.4063	0.043*
C21	0.1510 (2)	0.9574 (3)	0.4023 (2)	0.0352 (8)
C22	0.1583 (2)	1.0639 (2)	0.3948 (2)	0.0305 (8)
C23	0.1992 (3)	1.1083 (3)	0.3340 (2)	0.0381 (9)
H23	0.2259	1.0727	0.2955	0.046*
C24	0.1997 (3)	1.2072 (2)	0.3315 (3)	0.0392 (9)
H24	0.2265	1.2367	0.2896	0.047*
C25	0.1267 (3)	1.2190 (3)	0.4458 (3)	0.0386 (9)
H25	0.1036	1.2567	0.4854	0.046*
C26	0.1205 (2)	1.1212 (3)	0.4521 (2)	0.0372 (9)
H26	0.0919	1.0936	0.4935	0.045*
O5	0.89687 (19)	0.9980 (2)	0.33618 (19)	0.0566 (8)
H1W	0.9471	0.9752	0.3683	0.085*
H2W	0.9002	1.0018	0.2829	0.085*
O6	0.10303 (19)	0.4671 (2)	0.1547 (2)	0.0618 (8)
H3W	0.0890	0.4581	0.2031	0.093*
H4W	0.0571	0.4882	0.1161	0.093*

	U11	U22	U33	U12	U13	U23
Hg1	0.03055 (8)	0.02692 (10)	0.04319 (9)	0.00303 (6)	0.01399 (6)	0.00319 (6)
Hg2	0.03092 (8)	0.02783 (10)	0.04418 (9)	0.00243 (6)	0.01377 (6)	0.00243 (6)
Cl1	0.0326 (5)	0.0563 (7)	0.0615 (7)	0.0070 (4)	0.0225 (5)	0.0088 (5)
Cl2	0.0337 (5)	0.0583 (7)	0.0585 (7)	0.0064 (4)	0.0213 (5)	0.0088 (5)
O1	0.0416 (15)	0.0241 (15)	0.0673 (19)	−0.0017 (11)	0.0136 (14)	0.0059 (13)
O2	0.0427 (16)	0.0345 (16)	0.092 (2)	−0.0030 (12)	0.0304 (16)	0.0051 (15)
O3	0.0496 (17)	0.0181 (14)	0.074 (2)	0.0002 (12)	0.0163 (14)	0.0048 (14)
O4	0.0429 (16)	0.0295 (16)	0.081 (2)	−0.0021 (12)	0.0254 (15)	0.0056 (14)
N1	0.0407 (18)	0.0175 (16)	0.0423 (18)	0.0007 (13)	0.0085 (15)	0.0004 (13)
N2	0.0329 (16)	0.0204 (17)	0.0505 (19)	−0.0019 (12)	0.0151 (14)	−0.0009 (13)
N3	0.045 (2)	0.026 (2)	0.047 (2)	0.0007 (13)	0.0098 (16)	0.0011 (14)
N4	0.0443 (19)	0.0212 (17)	0.0430 (19)	−0.0063 (14)	0.0108 (15)	−0.0037 (14)
N5	0.0349 (17)	0.0217 (17)	0.0505 (19)	−0.0045 (13)	0.0135 (14)	−0.0018 (14)
N6	0.0408 (18)	0.0281 (19)	0.050 (2)	0.0005 (14)	0.0120 (16)	0.0004 (15)
C1	0.0333 (19)	0.0218 (19)	0.0300 (19)	0.0068 (14)	0.0103 (15)	0.0038 (14)
C2	0.040 (2)	0.028 (2)	0.037 (2)	0.0015 (16)	0.0096 (17)	0.0025 (16)
C3	0.048 (2)	0.025 (2)	0.057 (3)	0.0112 (18)	0.014 (2)	0.0000 (18)
C4	0.042 (2)	0.041 (3)	0.063 (3)	0.0197 (19)	0.010 (2)	0.004 (2)
C5	0.032 (2)	0.035 (2)	0.054 (3)	−0.0009 (16)	0.0046 (18)	0.0005 (18)
C6	0.036 (2)	0.025 (2)	0.034 (2)	0.0047 (15)	0.0097 (16)	−0.0003 (15)
C7	0.037 (2)	0.025 (2)	0.038 (2)	−0.0028 (15)	0.0117 (17)	−0.0013 (16)
C8	0.036 (2)	0.024 (2)	0.044 (2)	−0.0021 (16)	0.0075 (17)	0.0039 (16)
C9	0.0301 (18)	0.021 (2)	0.037 (2)	0.0014 (14)	0.0052 (15)	0.0032 (15)
C10	0.037 (2)	0.029 (2)	0.044 (2)	−0.0006 (16)	0.0154 (18)	0.0009 (17)
C11	0.039 (2)	0.030 (2)	0.046 (2)	0.0082 (16)	0.0132 (18)	−0.0025 (18)
C12	0.049 (2)	0.037 (3)	0.042 (2)	−0.0021 (18)	0.0186 (19)	0.0061 (19)
C13	0.052 (2)	0.024 (2)	0.044 (2)	0.0024 (17)	0.0164 (19)	−0.0021 (17)
C14	0.0347 (19)	0.023 (2)	0.0320 (19)	0.0054 (14)	0.0118 (16)	0.0031 (15)
C15	0.038 (2)	0.026 (2)	0.033 (2)	0.0030 (15)	0.0092 (17)	0.0014 (15)
C16	0.034 (2)	0.040 (3)	0.057 (3)	0.0023 (17)	0.0062 (19)	−0.0017 (19)
C17	0.038 (2)	0.041 (3)	0.070 (3)	0.0165 (18)	0.006 (2)	0.005 (2)
C18	0.048 (2)	0.026 (2)	0.058 (3)	0.0120 (18)	0.009 (2)	0.0042 (18)
C19	0.041 (2)	0.023 (2)	0.040 (2)	−0.0009 (16)	0.0077 (17)	0.0044 (16)
C20	0.034 (2)	0.028 (2)	0.046 (2)	−0.0025 (16)	0.0108 (17)	−0.0024 (17)
C21	0.031 (2)	0.032 (2)	0.041 (2)	−0.0013 (16)	0.0066 (17)	−0.0004 (17)
C22	0.0282 (18)	0.023 (2)	0.039 (2)	0.0017 (14)	0.0065 (16)	0.0007 (16)
C23	0.047 (2)	0.034 (2)	0.037 (2)	0.0030 (17)	0.0175 (18)	−0.0026 (17)
C24	0.050 (2)	0.026 (2)	0.046 (2)	−0.0040 (16)	0.0194 (19)	0.0040 (17)
C25	0.040 (2)	0.030 (2)	0.048 (2)	0.0069 (16)	0.0135 (19)	−0.0033 (17)
C26	0.034 (2)	0.040 (2)	0.041 (2)	0.0041 (16)	0.0151 (17)	0.0042 (17)
O5	0.0477 (17)	0.068 (2)	0.0577 (19)	0.0121 (15)	0.0196 (15)	0.0016 (15)
O6	0.0449 (17)	0.072 (2)	0.071 (2)	0.0108 (15)	0.0201 (16)	−0.0060 (17)

Hg1—C1	2.059 (3)	C8—C9	1.501 (5)
Hg1—Cl1	2.3189 (9)	C9—C13	1.390 (5)
Hg2—C14	2.058 (3)	C9—C10	1.389 (5)
Hg2—Cl2	2.3231 (10)	C10—C11	1.379 (5)
O1—C2	1.366 (4)	C10—H10	0.9300
O1—H1	0.8200	C11—H11	0.9300
O2—C8	1.233 (4)	C12—C13	1.379 (5)
O3—C19	1.369 (4)	C12—H12	0.9300
O3—H3	0.8200	C13—H13	0.9300
O4—C21	1.237 (4)	C14—C19	1.391 (5)
N1—C7	1.268 (4)	C14—C15	1.402 (5)
N1—N2	1.382 (4)	C15—C16	1.400 (5)
N2—C8	1.354 (4)	C15—C20	1.468 (5)
N2—H2D	0.8600	C16—C17	1.383 (5)
N3—C12	1.340 (5)	C16—H16	0.9300
N3—C11	1.341 (5)	C17—C18	1.379 (5)
N4—C20	1.277 (4)	C17—H17	0.9300
N4—N5	1.386 (4)	C18—C19	1.389 (5)
N5—C21	1.353 (4)	C18—H18	0.9300
N5—H5D	0.8600	C20—H20	0.9300
N6—C24	1.323 (4)	C21—C22	1.502 (5)
N6—C25	1.345 (4)	C22—C23	1.379 (5)
C1—C2	1.388 (5)	C22—C26	1.402 (5)
C1—C6	1.405 (5)	C23—C24	1.387 (5)
C2—C3	1.397 (5)	C23—H23	0.9300
C3—C4	1.384 (5)	C24—H24	0.9300
C3—H3A	0.9300	C25—C26	1.378 (5)
C4—C5	1.389 (5)	C25—H25	0.9300
C4—H4	0.9300	C26—H26	0.9300
C5—C6	1.392 (5)	O5—H1W	0.8363
C5—H5	0.9300	O5—H2W	0.8344
C6—C7	1.473 (5)	O6—H3W	0.8298
C7—H7	0.9300	O6—H4W	0.8293
C1—Hg1—Cl1	173.85 (10)	N3—C12—C13	123.8 (3)
C14—Hg2—Cl2	174.67 (10)	N3—C12—H12	118.1
C2—O1—H1	109.5	C13—C12—H12	118.1
C19—O3—H3	109.5	C12—C13—C9	118.5 (3)
C7—N1—N2	116.7 (3)	C12—C13—H13	120.7
C8—N2—N1	117.6 (3)	C9—C13—H13	120.7
C8—N2—H2D	121.2	C19—C14—C15	118.8 (3)
N1—N2—H2D	121.2	C19—C14—Hg2	119.7 (3)
C12—N3—C11	117.0 (3)	C15—C14—Hg2	121.4 (2)
C20—N4—N5	116.5 (3)	C16—C15—C14	119.8 (3)
C21—N5—N4	118.5 (3)	C16—C15—C20	118.0 (3)
C21—N5—H5D	120.7	C14—C15—C20	122.2 (3)
N4—N5—H5D	120.7	C17—C16—C15	120.2 (4)
C24—N6—C25	117.4 (3)	C17—C16—H16	119.9
C2—C1—C6	119.5 (3)	C15—C16—H16	119.9
C2—C1—Hg1	119.4 (3)	C18—C17—C16	120.2 (4)
C6—C1—Hg1	121.1 (2)	C18—C17—H17	119.9
O1—C2—C1	117.6 (3)	C16—C17—H17	119.9
O1—C2—C3	122.0 (3)	C17—C18—C19	119.9 (4)
C1—C2—C3	120.3 (3)	C17—C18—H18	120.0
C4—C3—C2	120.0 (4)	C19—C18—H18	120.0
C4—C3—H3A	120.0	O3—C19—C18	121.7 (3)
C2—C3—H3A	120.0	O3—C19—C14	117.2 (3)
C3—C4—C5	120.2 (3)	C18—C19—C14	121.0 (3)
C3—C4—H4	119.9	N4—C20—C15	120.3 (3)
C5—C4—H4	119.9	N4—C20—H20	119.9
C4—C5—C6	120.2 (3)	C15—C20—H20	119.9
C4—C5—H5	119.9	O4—C21—N5	123.6 (3)
C6—C5—H5	119.9	O4—C21—C22	121.2 (3)
C5—C6—C1	119.8 (3)	N5—C21—C22	115.2 (3)
C5—C6—C7	118.3 (3)	C23—C22—C26	118.4 (3)
C1—C6—C7	121.9 (3)	C23—C22—C21	123.4 (3)
N1—C7—C6	120.6 (3)	C26—C22—C21	118.3 (3)
N1—C7—H7	119.7	C22—C23—C24	118.3 (3)
C6—C7—H7	119.7	C22—C23—H23	120.8
O2—C8—N2	123.6 (3)	C24—C23—H23	120.8
O2—C8—C9	121.0 (3)	N6—C24—C23	124.1 (3)
N2—C8—C9	115.4 (3)	N6—C24—H24	117.9
C13—C9—C10	118.2 (3)	C23—C24—H24	117.9
C13—C9—C8	123.1 (3)	N6—C25—C26	122.9 (3)
C10—C9—C8	118.7 (3)	N6—C25—H25	118.6
C11—C10—C9	119.1 (3)	C26—C25—H25	118.6
C11—C10—H10	120.5	C25—C26—C22	118.8 (3)
C9—C10—H10	120.5	C25—C26—H26	120.6
N3—C11—C10	123.3 (3)	C22—C26—H26	120.6
N3—C11—H11	118.4	H1W—O5—H2W	110.1
C10—C11—H11	118.4	H3W—O6—H4W	111.0
C7—N1—N2—C8	163.9 (3)	C8—C9—C13—C12	−179.9 (3)
C20—N4—N5—C21	−166.2 (3)	Cl2—Hg2—C14—C19	2.9 (12)
Cl1—Hg1—C1—C2	−23.9 (11)	Cl2—Hg2—C14—C15	−176.6 (8)
Cl1—Hg1—C1—C6	155.6 (7)	C19—C14—C15—C16	1.2 (5)
C6—C1—C2—O1	177.6 (3)	Hg2—C14—C15—C16	−179.3 (3)
Hg1—C1—C2—O1	−2.8 (4)	C19—C14—C15—C20	178.7 (3)
C6—C1—C2—C3	1.2 (5)	Hg2—C14—C15—C20	−1.8 (5)
Hg1—C1—C2—C3	−179.2 (3)	C14—C15—C16—C17	−0.4 (6)
O1—C2—C3—C4	−177.4 (4)	C20—C15—C16—C17	−178.0 (4)
C1—C2—C3—C4	−1.1 (6)	C15—C16—C17—C18	0.1 (6)
C2—C3—C4—C5	0.8 (6)	C16—C17—C18—C19	−0.6 (6)
C3—C4—C5—C6	−0.6 (6)	C17—C18—C19—O3	178.0 (4)
C4—C5—C6—C1	0.8 (6)	C17—C18—C19—C14	1.4 (6)
C4—C5—C6—C7	179.7 (3)	C15—C14—C19—O3	−178.5 (3)
C2—C1—C6—C5	−1.1 (5)	Hg2—C14—C19—O3	2.1 (4)
Hg1—C1—C6—C5	179.4 (3)	C15—C14—C19—C18	−1.7 (5)
C2—C1—C6—C7	−179.9 (3)	Hg2—C14—C19—C18	178.8 (3)
Hg1—C1—C6—C7	0.5 (5)	N5—N4—C20—C15	−177.1 (3)
N2—N1—C7—C6	178.0 (3)	C16—C15—C20—N4	−179.3 (4)
C5—C6—C7—N1	176.9 (3)	C14—C15—C20—N4	3.2 (5)
C1—C6—C7—N1	−4.2 (5)	N4—N5—C21—O4	4.8 (5)
N1—N2—C8—O2	−4.8 (5)	N4—N5—C21—C22	−175.9 (3)
N1—N2—C8—C9	177.4 (3)	O4—C21—C22—C23	−143.1 (4)
O2—C8—C9—C13	145.8 (4)	N5—C21—C22—C23	37.6 (5)
N2—C8—C9—C13	−36.3 (5)	O4—C21—C22—C26	36.2 (5)
O2—C8—C9—C10	−33.8 (5)	N5—C21—C22—C26	−143.1 (3)
N2—C8—C9—C10	144.1 (3)	C26—C22—C23—C24	−1.0 (5)
C13—C9—C10—C11	1.5 (5)	C21—C22—C23—C24	178.3 (3)
C8—C9—C10—C11	−178.9 (3)	C25—N6—C24—C23	0.5 (6)
C12—N3—C11—C10	2.0 (5)	C22—C23—C24—N6	1.1 (6)
C9—C10—C11—N3	−2.5 (5)	C24—N6—C25—C26	−2.2 (5)
C11—N3—C12—C13	−0.6 (5)	N6—C25—C26—C22	2.3 (5)
N3—C12—C13—C9	−0.2 (6)	C23—C22—C26—C25	−0.6 (5)
C10—C9—C13—C12	−0.3 (5)	C21—C22—C26—C25	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H4W···O2i	0.83	2.15	2.898 (4)	150
O6—H3W···O3	0.83	2.30	3.023 (4)	146
O5—H2W···O1	0.83	2.17	2.963 (4)	159
O5—H1W···O4ii	0.84	2.06	2.876 (4)	166
N5—H5D···O6iii	0.86	2.04	2.872 (4)	162
N2—H2D···O5iv	0.86	2.06	2.890 (4)	161
O3—H3···N6v	0.82	1.92	2.737 (4)	171
O1—H1···N3vi	0.82	1.93	2.733 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H4W⋯O2i	0.83	2.15	2.898 (4)	150
O6—H3W⋯O3	0.83	2.30	3.023 (4)	146
O5—H2W⋯O1	0.83	2.17	2.963 (4)	159
O5—H1W⋯O4ii	0.84	2.06	2.876 (4)	166
N5—H5D⋯O6iii	0.86	2.04	2.872 (4)	162
N2—H2D⋯O5iv	0.86	2.06	2.890 (4)	161
O3—H3⋯N6v	0.82	1.92	2.737 (4)	171
O1—H1⋯N3vi	0.82	1.93	2.733 (4)	167

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