Aqua-bis[N'-(2-hydroxy-benzyl-idene)isonicotinohydrazide-κN]silver(I) nitrate.

In the title compound, [Ag(C(13)H(11)N(3)O(2))(2)(H(2)O)]NO(3), two N atoms from two pyridine rings of two N'-(2-hydroxy-benzyl-idene)isonicotinohydrazide ligands coordinate to the Ag(I) atom, forming a nearly linear geometry with an N-Ag-N angle of 171.63 (6)°; a water O atom is located at the apical site, completing the T-shaped coordination. The crystal structure is stabilized by extensive O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonding.

Related literature

For factors affecting the coordination geometry of silver, see: Dong et al. (2004 ▶); n class="Chemical">Niu et al. (2009a ▶); Sumby & Hardie (2005 ▶); Abu-Youssef et al. (2007 ▶). For related structures, see: Li et al. (2006 ▶); Näther & Beck (2004 ▶); Niu et al. (2009b ▶).

Experimental

Crystal data

[Ag(C13H11N3O2)2(H2O)]n class="Chemical">NO3

M = 670.39

Monoclinic,

a = 11.7194 (6) Å

b = 12.6459 (6) Å

c = 18.5719 (9) Å

β = 104.738 (1)°

V = 2661.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.82 mm−1

T = 120 K

0.55 × 0.45 × 0.30 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.686, T max = 0.791

26832 measured reflections

6427 independent reflections

5518 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.07

6427 reflections

403 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.04 e Å−3

Δρmin = −0.57 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT-Plus; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005027/pv2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005027/pv2256Isup2.hkl

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

[Ag(C13H11N3O2)2(H2O)]NO3	F(000) = 1360
Mr = 670.39	Dx = 1.673 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 530 reflections
a = 11.7194 (6) Å	θ = 3–28°
b = 12.6459 (6) Å	µ = 0.82 mm−1
c = 18.5719 (9) Å	T = 120 K
β = 104.738 (1)°	Prism, colourless
V = 2661.8 (2) Å3	0.55 × 0.45 × 0.30 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	6427 independent reflections
Radiation source: normal-focus sealed tube	5518 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −15→15
Tmin = 0.686, Tmax = 0.791	k = −16→16
26832 measured reflections	l = −24→24

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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0415P)2 + 1.2646P] where P = (Fo2 + 2Fc2)/3
6427 reflections	(Δ/σ)max = 0.002
403 parameters	Δρmax = 1.04 e Å−3
0 restraints	Δρmin = −0.57 e Å−3

Geometry. 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.

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 > 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.

	x	y	z	Uiso*/Ueq
Ag1	0.775957 (12)	0.740141 (11)	0.273949 (7)	0.02310 (6)
O1	0.34784 (12)	0.58945 (10)	−0.05478 (8)	0.0300 (3)
O2	0.13029 (13)	0.62068 (10)	−0.23755 (8)	0.0270 (3)
H2O	0.174 (2)	0.642 (2)	−0.1962 (14)	0.039 (7)*
O3	1.18823 (12)	0.93761 (10)	0.59595 (8)	0.0296 (3)
O4	1.41552 (13)	0.91337 (11)	0.78672 (8)	0.0281 (3)
H4O	1.373 (2)	0.8915 (19)	0.7484 (14)	0.036 (7)*
N1	0.64148 (14)	0.72810 (12)	0.17184 (8)	0.0205 (3)
N2	0.31651 (14)	0.76550 (12)	−0.06954 (8)	0.0187 (3)
H2N	0.3355 (19)	0.827 (2)	−0.0542 (12)	0.026 (6)*
N3	0.23344 (14)	0.74841 (11)	−0.13455 (9)	0.0184 (3)
N4	0.91745 (13)	0.77455 (12)	0.37111 (8)	0.0196 (3)
N5	1.23864 (14)	0.76411 (12)	0.61217 (9)	0.0187 (3)
H5N	1.239 (2)	0.700 (2)	0.5912 (15)	0.045 (7)*
N6	1.31761 (13)	0.78524 (12)	0.67872 (8)	0.0197 (3)
C2	0.59564 (16)	0.63071 (15)	0.14847 (10)	0.0246 (4)
H2A	0.6244	0.5710	0.1787	0.030*
C3	0.50945 (16)	0.61508 (14)	0.08293 (10)	0.0235 (4)
H3A	0.4807	0.5460	0.0687	0.028*
C4	0.46537 (15)	0.70135 (14)	0.03811 (9)	0.0194 (3)
C5	0.51035 (16)	0.80089 (14)	0.06191 (10)	0.0216 (3)
H5A	0.4820	0.8618	0.0329	0.026*
C6	0.59588 (16)	0.81041 (15)	0.12748 (10)	0.0229 (4)
H6A	0.6248	0.8792	0.1426	0.027*
C7	0.37251 (15)	0.67941 (14)	−0.03274 (10)	0.0200 (3)
C8	0.17347 (15)	0.82700 (14)	−0.16895 (9)	0.0194 (3)
H8A	0.1879	0.8968	−0.1499	0.023*
C9	0.08375 (15)	0.80705 (14)	−0.23707 (10)	0.0200 (3)
C10	0.06388 (16)	0.70525 (15)	−0.26912 (10)	0.0210 (3)
C11	−0.02388 (17)	0.68925 (17)	−0.33365 (10)	0.0273 (4)
H11A	−0.0355	0.6209	−0.3555	0.033*
C12	−0.09495 (17)	0.77244 (17)	−0.36661 (11)	0.0280 (4)
H12A	−0.1553	0.7608	−0.4109	0.034*
C13	−0.07862 (17)	0.87339 (17)	−0.33525 (10)	0.0281 (4)
H13A	−0.1282	0.9302	−0.3575	0.034*
C14	0.01051 (16)	0.88956 (15)	−0.27153 (10)	0.0241 (4)
H14A	0.0224	0.9584	−0.2506	0.029*
C16	0.96229 (16)	0.87207 (14)	0.38692 (10)	0.0234 (4)
H16A	0.9344	0.9272	0.3522	0.028*
C17	1.04701 (16)	0.89570 (14)	0.45134 (10)	0.0231 (4)
H19B	1.0772	0.9655	0.4602	0.028*
C18	1.08769 (15)	0.81621 (14)	0.50305 (9)	0.0194 (3)
C19	1.04189 (16)	0.71489 (15)	0.48736 (10)	0.0207 (3)
H19A	1.0678	0.6587	0.5215	0.025*
C20	0.95837 (16)	0.69751 (14)	0.42146 (10)	0.0211 (3)
H20A	0.9280	0.6280	0.4109	0.025*
C21	1.17579 (15)	0.84614 (14)	0.57436 (9)	0.0200 (3)
C22	1.38215 (15)	0.70897 (14)	0.71241 (10)	0.0200 (3)
H22A	1.3736	0.6401	0.6913	0.024*
C23	1.46765 (16)	0.72811 (14)	0.78232 (10)	0.0209 (3)
C24	1.48193 (16)	0.82865 (15)	0.81647 (10)	0.0224 (4)
C25	1.56702 (17)	0.84345 (16)	0.88292 (10)	0.0279 (4)
H25A	1.5760	0.9109	0.9062	0.033*
C26	1.63897 (18)	0.76048 (17)	0.91552 (11)	0.0303 (4)
H26A	1.6972	0.7718	0.9608	0.036*
C27	1.62699 (17)	0.66057 (17)	0.88272 (11)	0.0309 (4)
H27A	1.6768	0.6040	0.9052	0.037*
C28	1.54123 (17)	0.64503 (16)	0.81680 (10)	0.0264 (4)
H28A	1.5320	0.5769	0.7945	0.032*
N7	0.23978 (14)	0.99376 (11)	−0.00096 (8)	0.0240 (3)
O5	0.14711 (16)	1.04260 (14)	−0.02193 (9)	0.0520 (5)
O6	0.31228 (13)	0.98880 (11)	−0.03995 (8)	0.0314 (3)
O7	0.26376 (13)	0.94629 (10)	0.06137 (7)	0.0284 (3)
O1W	0.76685 (14)	0.54006 (11)	0.30562 (9)	0.0308 (3)
H1W	0.759 (2)	0.519 (2)	0.3471 (15)	0.039 (7)*
H2W	0.801 (3)	0.496 (2)	0.2897 (16)	0.055 (9)*

	U11	U22	U33	U12	U13	U23
Ag1	0.01855 (9)	0.03073 (9)	0.01712 (8)	0.00154 (5)	−0.00076 (6)	0.00185 (5)
O1	0.0320 (7)	0.0221 (7)	0.0302 (7)	0.0029 (5)	−0.0025 (6)	−0.0047 (5)
O2	0.0318 (7)	0.0214 (6)	0.0253 (7)	−0.0001 (5)	0.0029 (6)	−0.0062 (5)
O3	0.0332 (7)	0.0218 (7)	0.0290 (7)	0.0022 (5)	−0.0009 (6)	−0.0058 (5)
O4	0.0323 (7)	0.0235 (7)	0.0249 (7)	−0.0031 (5)	0.0005 (6)	−0.0050 (5)
N1	0.0221 (8)	0.0266 (8)	0.0132 (7)	0.0085 (6)	0.0052 (6)	0.0035 (6)
N2	0.0184 (7)	0.0197 (7)	0.0154 (7)	−0.0004 (5)	−0.0008 (6)	−0.0019 (5)
N3	0.0173 (7)	0.0232 (7)	0.0146 (7)	−0.0013 (5)	0.0037 (6)	−0.0008 (5)
N4	0.0150 (7)	0.0264 (8)	0.0164 (7)	0.0022 (6)	0.0021 (6)	0.0014 (6)
N5	0.0191 (7)	0.0195 (7)	0.0159 (7)	−0.0015 (5)	0.0013 (6)	−0.0021 (5)
N6	0.0180 (7)	0.0246 (7)	0.0152 (7)	−0.0021 (6)	0.0020 (6)	−0.0019 (6)
C2	0.0235 (9)	0.0239 (9)	0.0252 (9)	0.0064 (7)	0.0039 (7)	0.0050 (7)
C3	0.0244 (9)	0.0212 (8)	0.0238 (9)	0.0037 (7)	0.0040 (7)	0.0011 (7)
C4	0.0196 (8)	0.0206 (8)	0.0185 (8)	0.0033 (6)	0.0057 (7)	0.0011 (6)
C5	0.0213 (9)	0.0209 (9)	0.0219 (9)	0.0012 (7)	0.0038 (7)	0.0013 (7)
C6	0.0219 (9)	0.0231 (9)	0.0223 (9)	−0.0023 (7)	0.0029 (7)	0.0010 (7)
C7	0.0171 (8)	0.0233 (8)	0.0190 (8)	0.0028 (6)	0.0037 (6)	−0.0002 (6)
C8	0.0198 (8)	0.0198 (8)	0.0178 (8)	−0.0020 (6)	0.0034 (6)	−0.0018 (6)
C9	0.0202 (8)	0.0222 (8)	0.0183 (8)	−0.0035 (7)	0.0057 (7)	−0.0006 (6)
C10	0.0201 (8)	0.0241 (9)	0.0200 (8)	−0.0031 (7)	0.0071 (7)	−0.0011 (7)
C11	0.0253 (9)	0.0357 (11)	0.0205 (9)	−0.0067 (8)	0.0054 (7)	−0.0057 (8)
C12	0.0178 (9)	0.0488 (12)	0.0149 (8)	−0.0055 (8)	−0.0005 (7)	0.0011 (8)
C13	0.0230 (9)	0.0377 (11)	0.0226 (9)	0.0023 (8)	0.0039 (7)	0.0087 (8)
C14	0.0269 (9)	0.0248 (9)	0.0206 (9)	−0.0011 (7)	0.0062 (7)	0.0024 (7)
C16	0.0252 (9)	0.0213 (8)	0.0234 (9)	0.0046 (7)	0.0059 (7)	0.0044 (7)
C17	0.0263 (9)	0.0190 (8)	0.0237 (9)	0.0006 (7)	0.0054 (7)	−0.0001 (7)
C18	0.0192 (8)	0.0207 (8)	0.0189 (8)	0.0020 (6)	0.0060 (7)	−0.0010 (6)
C19	0.0197 (8)	0.0217 (8)	0.0197 (8)	−0.0001 (7)	0.0034 (7)	0.0030 (7)
C20	0.0222 (8)	0.0200 (8)	0.0188 (8)	−0.0012 (7)	0.0014 (7)	0.0012 (6)
C21	0.0196 (8)	0.0213 (8)	0.0192 (8)	0.0003 (6)	0.0053 (7)	−0.0006 (6)
C22	0.0214 (8)	0.0198 (8)	0.0183 (8)	−0.0023 (7)	0.0040 (7)	−0.0009 (6)
C23	0.0191 (8)	0.0260 (9)	0.0174 (8)	−0.0034 (7)	0.0042 (7)	0.0009 (7)
C24	0.0203 (8)	0.0262 (9)	0.0208 (8)	−0.0057 (7)	0.0056 (7)	0.0002 (7)
C25	0.0262 (10)	0.0348 (10)	0.0219 (9)	−0.0109 (8)	0.0046 (7)	−0.0032 (8)
C26	0.0202 (9)	0.0496 (13)	0.0180 (9)	−0.0098 (8)	−0.0006 (7)	0.0044 (8)
C27	0.0241 (10)	0.0411 (11)	0.0261 (10)	0.0006 (8)	0.0036 (8)	0.0104 (8)
C28	0.0261 (9)	0.0283 (9)	0.0242 (9)	0.0001 (7)	0.0052 (7)	0.0046 (7)
N7	0.0332 (8)	0.0160 (7)	0.0185 (7)	0.0010 (6)	−0.0012 (6)	−0.0018 (5)
O5	0.0536 (11)	0.0551 (11)	0.0430 (9)	0.0335 (9)	0.0045 (8)	0.0096 (8)
O6	0.0413 (8)	0.0264 (7)	0.0276 (7)	−0.0055 (6)	0.0108 (6)	−0.0014 (5)
O7	0.0404 (8)	0.0210 (6)	0.0192 (6)	−0.0051 (6)	−0.0007 (6)	0.0023 (5)
O1W	0.0431 (9)	0.0238 (7)	0.0281 (8)	0.0042 (6)	0.0138 (7)	0.0015 (6)

Ag1—N1	2.1406 (16)	C10—C11	1.381 (3)
Ag1—N4	2.1616 (15)	C11—C12	1.384 (3)
Ag1—O1W	2.6059 (14)	C11—H11A	0.9500
O1—C7	1.219 (2)	C12—C13	1.396 (3)
O2—C10	1.364 (2)	C12—H12A	0.9500
O2—H2O	0.85 (3)	C13—C14	1.380 (3)
O3—C21	1.221 (2)	C13—H13A	0.9500
O4—C24	1.356 (2)	C14—H14A	0.9500
O4—H4O	0.81 (3)	C16—C17	1.379 (3)
N1—C6	1.350 (2)	C16—H16A	0.9500
N1—C2	1.369 (2)	C17—C18	1.388 (2)
N2—N3	1.362 (2)	C17—H19B	0.9500
N2—C7	1.362 (2)	C18—C19	1.391 (3)
N2—H2N	0.83 (2)	C18—C21	1.506 (2)
N3—C8	1.289 (2)	C19—C20	1.377 (2)
N4—C16	1.343 (2)	C19—H19A	0.9500
N4—C20	1.351 (2)	C20—H20A	0.9500
N5—C21	1.360 (2)	C22—C23	1.444 (3)
N5—N6	1.369 (2)	C22—H22A	0.9500
N5—H5N	0.90 (3)	C23—C28	1.406 (3)
N6—C22	1.286 (2)	C23—C24	1.412 (3)
C2—C3	1.384 (3)	C24—C25	1.388 (3)
C2—H2A	0.9500	C25—C26	1.385 (3)
C3—C4	1.390 (2)	C25—H25A	0.9500
C3—H3A	0.9500	C26—C27	1.394 (3)
C4—C5	1.393 (3)	C26—H26A	0.9500
C4—C7	1.505 (2)	C27—C28	1.386 (3)
C5—C6	1.372 (2)	C27—H27A	0.9500
C5—H5A	0.9500	C28—H28A	0.9500
C6—H6A	0.9500	N7—O5	1.224 (2)
C8—C9	1.447 (2)	N7—O6	1.250 (2)
C8—H8A	0.9500	N7—O7	1.2705 (19)
C9—C14	1.398 (2)	O1W—H1W	0.84 (3)
C9—C10	1.412 (3)	O1W—H2W	0.79 (3)
N1—Ag1—N4	171.63 (6)	C13—C12—H12A	119.8
N1—Ag1—O1W	93.88 (5)	C14—C13—C12	119.12 (18)
N4—Ag1—O1W	94.23 (5)	C14—C13—H13A	120.4
C10—O2—H2O	106.6 (17)	C12—C13—H13A	120.4
C24—O4—H4O	104.5 (18)	C13—C14—C9	121.63 (18)
C6—N1—C2	115.94 (16)	C13—C14—H14A	119.2
C6—N1—Ag1	125.00 (13)	C9—C14—H14A	119.2
C2—N1—Ag1	119.07 (11)	N4—C16—C17	122.94 (16)
N3—N2—C7	117.57 (15)	N4—C16—H16A	118.5
N3—N2—H2N	121.2 (15)	C17—C16—H16A	118.5
C7—N2—H2N	121.1 (15)	C16—C17—C18	119.21 (17)
C8—N3—N2	119.60 (14)	C16—C17—H19B	120.4
C16—N4—C20	117.42 (16)	C18—C17—H19B	120.4
C16—N4—Ag1	122.79 (12)	C17—C18—C19	118.41 (16)
C20—N4—Ag1	119.63 (12)	C17—C18—C21	117.67 (16)
C21—N5—N6	118.07 (15)	C19—C18—C21	123.88 (16)
C21—N5—H5N	121.6 (17)	C20—C19—C18	118.85 (17)
N6—N5—H5N	119.4 (17)	C20—C19—H19A	120.6
C22—N6—N5	118.16 (15)	C18—C19—H19A	120.6
N1—C2—C3	123.16 (16)	N4—C20—C19	123.17 (17)
N1—C2—H2A	118.4	N4—C20—H20A	118.4
C3—C2—H2A	118.4	C19—C20—H20A	118.4
C2—C3—C4	119.45 (17)	O3—C21—N5	123.33 (16)
C2—C3—H3A	120.3	O3—C21—C18	121.66 (16)
C4—C3—H3A	120.3	N5—C21—C18	115.00 (15)
C3—C4—C5	117.81 (17)	N6—C22—C23	119.96 (16)
C3—C4—C7	117.06 (16)	N6—C22—H22A	120.0
C5—C4—C7	125.13 (16)	C23—C22—H22A	120.0
C6—C5—C4	119.55 (17)	C28—C23—C24	118.66 (17)
C6—C5—H5A	120.2	C28—C23—C22	119.27 (17)
C4—C5—H5A	120.2	C24—C23—C22	122.05 (17)
N1—C6—C5	124.09 (17)	O4—C24—C25	117.62 (17)
N1—C6—H6A	118.0	O4—C24—C23	122.56 (16)
C5—C6—H6A	118.0	C25—C24—C23	119.82 (18)
O1—C7—N2	122.33 (16)	C26—C25—C24	120.42 (19)
O1—C7—C4	121.53 (16)	C26—C25—H25A	119.8
N2—C7—C4	116.13 (15)	C24—C25—H25A	119.8
N3—C8—C9	118.84 (16)	C25—C26—C27	120.87 (19)
N3—C8—H8A	120.6	C25—C26—H26A	119.6
C9—C8—H8A	120.6	C27—C26—H26A	119.6
C14—C9—C10	118.10 (16)	C28—C27—C26	118.96 (19)
C14—C9—C8	119.67 (16)	C28—C27—H27A	120.5
C10—C9—C8	122.18 (16)	C26—C27—H27A	120.5
O2—C10—C11	118.38 (17)	C27—C28—C23	121.28 (19)
O2—C10—C9	121.24 (16)	C27—C28—H28A	119.4
C11—C10—C9	120.38 (18)	C23—C28—H28A	119.4
C10—C11—C12	120.25 (19)	O5—N7—O6	121.33 (16)
C10—C11—H11A	119.9	O5—N7—O7	120.08 (17)
C12—C11—H11A	119.9	O6—N7—O7	118.59 (15)
C11—C12—C13	120.50 (18)	H1W—O1W—H2W	108 (3)
C11—C12—H12A	119.8
O1W—Ag1—N1—C6	175.36 (14)	C12—C13—C14—C9	−0.9 (3)
O1W—Ag1—N1—C2	−4.07 (14)	C10—C9—C14—C13	−0.3 (3)
O1W—Ag1—N4—C16	−178.91 (14)	C8—C9—C14—C13	−177.92 (17)
O1W—Ag1—N4—C20	−3.61 (14)	C20—N4—C16—C17	0.1 (3)
C7—N2—N3—C8	175.98 (16)	Ag1—N4—C16—C17	175.52 (14)
C21—N5—N6—C22	−175.93 (16)	N4—C16—C17—C18	−0.7 (3)
C6—N1—C2—C3	1.2 (3)	C16—C17—C18—C19	0.6 (3)
Ag1—N1—C2—C3	−179.31 (14)	C16—C17—C18—C21	−177.08 (16)
N1—C2—C3—C4	−0.5 (3)	C17—C18—C19—C20	0.0 (3)
C2—C3—C4—C5	−0.3 (3)	C21—C18—C19—C20	177.56 (17)
C2—C3—C4—C7	179.53 (16)	C16—N4—C20—C19	0.6 (3)
C3—C4—C5—C6	0.4 (3)	Ag1—N4—C20—C19	−174.99 (14)
C7—C4—C5—C6	−179.42 (17)	C18—C19—C20—N4	−0.6 (3)
C2—N1—C6—C5	−1.1 (3)	N6—N5—C21—O3	1.7 (3)
Ag1—N1—C6—C5	179.44 (14)	N6—N5—C21—C18	−177.92 (14)
C4—C5—C6—N1	0.3 (3)	C17—C18—C21—O3	19.3 (3)
N3—N2—C7—O1	−2.5 (3)	C19—C18—C21—O3	−158.27 (18)
N3—N2—C7—C4	178.87 (15)	C17—C18—C21—N5	−161.04 (16)
C3—C4—C7—O1	−9.2 (3)	C19—C18—C21—N5	21.4 (2)
C5—C4—C7—O1	170.63 (17)	N5—N6—C22—C23	179.24 (16)
C3—C4—C7—N2	169.47 (16)	N6—C22—C23—C28	−177.15 (17)
C5—C4—C7—N2	−10.7 (3)	N6—C22—C23—C24	1.2 (3)
N2—N3—C8—C9	−178.63 (15)	C28—C23—C24—O4	179.40 (17)
N3—C8—C9—C14	174.16 (16)	C22—C23—C24—O4	1.0 (3)
N3—C8—C9—C10	−3.3 (3)	C28—C23—C24—C25	−0.3 (3)
C14—C9—C10—O2	−178.56 (16)	C22—C23—C24—C25	−178.70 (17)
C8—C9—C10—O2	−1.0 (3)	O4—C24—C25—C26	−178.97 (17)
C14—C9—C10—C11	1.5 (3)	C23—C24—C25—C26	0.8 (3)
C8—C9—C10—C11	179.04 (17)	C24—C25—C26—C27	−0.4 (3)
O2—C10—C11—C12	178.61 (16)	C25—C26—C27—C28	−0.3 (3)
C9—C10—C11—C12	−1.5 (3)	C26—C27—C28—C23	0.8 (3)
C10—C11—C12—C13	0.2 (3)	C24—C23—C28—C27	−0.4 (3)
C11—C12—C13—C14	1.0 (3)	C22—C23—C28—C27	177.98 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7i	0.84 (3)	2.01 (3)	2.844 (2)	171 (3)
O1W—H2W···O2ii	0.79 (3)	2.04 (3)	2.821 (2)	172 (3)
N2—H2N···O6	0.84 (3)	2.09 (3)	2.880 (2)	157 (2)
N5—H5N···O7iii	0.90 (3)	1.97 (3)	2.863 (2)	169 (2)
O2—H2O···N3	0.85 (3)	1.79 (3)	2.560 (2)	150 (2)
O4—H4O···N6	0.81 (2)	1.86 (2)	2.607 (2)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O7i	0.84 (3)	2.01 (3)	2.844 (2)	171 (3)
O1W—H2W⋯O2ii	0.79 (3)	2.04 (3)	2.821 (2)	172 (3)
N2—H2N⋯O6	0.84 (3)	2.09 (3)	2.880 (2)	157 (2)
N5—H5N⋯O7iii	0.90 (3)	1.97 (3)	2.863 (2)	169 (2)
O2—H2O⋯N3	0.85 (3)	1.79 (3)	2.560 (2)	150 (2)
O4—H4O⋯N6	0.81 (2)	1.86 (2)	2.607 (2)	153 (2)

Symmetry codes: (i) ; (ii) ; (iii) .