N-(2-{[(1E)-1-(2-Hydroxy­phen­yl)ethyl­idene]amino}phen­yl)-2-methoxy­acet­amide

Mol­ecules of the title compound, C₁₇H₁₈N₂O₃, are linked by paired C—H...O hydrogen-bonding inter­actions into R₂²(8) dimers. The mol­ecule is not planar. The dihedral angle between the two benzene rings is 64.17 (7)°. The mol­ecular conformation is stabilized by intra­molecular O—H...N, N—H...N and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.098
• Data-to-parameter ratio = 18.3

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S1. Comment

Schiff bases and their biologically active complexes have been often used as chelating ligands in the coordination chemistry of transition metals as radiopharmaceuticals for cancer targeting, agrochemicals, as model systems for biological macromolecules, as catalysts and as dioxygen carriers (Ünaleroğlu et al., 2001; Li & Chang, 1991; Blower, 1998; Berkessel et al., 1997). The phenyl derivatives of Schiff bases are used as corrosion inhibitors. Schiff bases derived from aldehyde and diamines constitute one of the most relevant synthetic ligand systems with importance in asymmetric catalysis and they appear to be of importance for a broad range of transition-metal catalyzed reactions including lactide polymerization, epoxidation of olefins, hydroxylation and asymmetric ring opening of epoxides (Kovbasyuk et al., 1997; Ho et al., 1996; Topich & Bachert, 1992; Larrow et al., 1994; Jacobsen, 1993; Irie et al., 1990; Srinivasan & Kochi, 1985; Kickelbick et al., 2003). Although a series of Schiff base complexes have been studied crystallographically, there are only a very limited number of reports about the free Schiff bases in the literature (Amirnasr, Schenk, Meghdadi & Morshedi, 2006; Amirnasr, DehnoKhalaji & Falvello, 2006; Amirnasr et al., 2002; Amirnasr et al., 2001; Habibi et al., 2006). Schiff bases have antibacterial, antimalarial, antiviral and antitumor activities (Yıldız et al., 2005; Indreen et al., 2001; Jarrahpour, Motamedifar, Pakshir, Hadi & Zarei,, 2004; Jarrahpour, Motamedifar, Hadi & Zarei, 2004; Holla et al., 2005; Nawrocka et al., 2004; Lozytska et al., 2004).

In Fig. 1, the molecular conformation of the title compound was shown with the intramolecular N—H···O, N—H···N, O—H···N and C—H···O hydrogen-bond distances of 1.725 (19), 2.062 (15), 2.363 (15) and 2.34 Å, respectively. In the molecular structure all the bond distances and angles are normal. The molecular structure is not planar. The C1—C6 and C9—C14 benzene rings makes a dihedral angle of 64.17 (7) ° with each other.

The molecules of are linked by intermolecular C—H···O hydrogen bonding interactions, generating a centrosymmetric R₂²(8) dimer (Fig. 2).

Related literature

For related literature, see: Amirnasr, DehnoKhalaji & Falvello (2006); Amirnasr et al. (2001, 2002); Amirnasr, Schenk, Meghdadi & Morshedi (2006); Berkessel et al. (1997); Blower (1998); Habibi et al. (2006); Ho et al. (1996); Holla et al. (2005); Indreen et al. (2001); Irie et al. (1990); Jacobsen (1993); Jarrahpour, Motamedifar, Hadi & Zarei (2004); Jarrahpour, Motamedifar, Pakshir, Hadi & Zarei (2004); Kickelbick et al. (2003); Kovbasyuk et al. (1997); Larrow et al. (1994); Li & Chang (1991); Lozytska et al. (2004); Nawrocka et al. (2004); Srinivasan & Kochi (1985); Topich & Bachert (1992); Ünaleroğlu et al. (2001); Yıldız, Ünver, Dülger, Erdener, Ocak, Erdönmez & Durlu (2005).

S2. Experimental

Schiff base {2-[(1E)-N-(2-aminophenyl)ethanimidoyl]phenol} (0.23 g, 1.0 mmol) was transformed to N-(2-{[(1E)-1-(2-hydroxyphenyl)- ethylidene]amino}phenyl)-2-methoxyacetamide, (I), by treatment with methoxyacetyl chloride (0.13 g, 1.2 mmol) and triethylamine (0.26 g, 2.6 mmol) in dry methylene chloride (10 ml) with cooling in ice-salt bath. The reaction progress was monitored by TLC and the presence of a new compound was confirmed. The IR spectrum showed the characteristic absorption of the amide carbonyl at 1752, the C=N moiety at 1689 and the amine group at 3386 cm^-1. The ¹H-NMR spectrum showed the methoxy protons at 3.27, methyl protons at 2.29, amine protons at 3.89, aromatic protons at 6.75–7.61, and hydroxyl proton at 13.97. The ¹³C-NMR spectrum exhibited the following signals: CH₃ at 17.69, OCH₃ at 59.44, aromatic carbons at 118.31–133.68, Ph—C—N at 160.0, Ph—C—OH at 165.0, and the C=O at 174.0.The mass spectrum showed peaks at 298 (M⁺), 299 (M+1), 300 (M+2) and the base peak at 253 (C₁₅H₁₃N₂O₂).

S3. Refinement

The H atoms of the hydroxyl and amine groups were found from a difference Fourier map and refined freely. The other H atoms were located geometrically and treated as riding atoms with C—H = 0.93–0.97 Å, and with U_iso(H) = 1.2 U_eq(C) for aromatic and methelene H atoms and 1.5 U_eq(C) for methyl H atoms.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: SADABS (Sheldrick, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1994) or SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

	Fig. 1. View of the title compound (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the hydrogen bonding of the title compound. Dashed lines show hydrogen bonds. For clarity, H atoms not involved hydrogen bonding have been omitted.

N-(2-{[(1E)-1-(2-Hydroxyphenyl)ethylidene]amino}phenyl)-2-methoxyacetamide

Crystal data

C17H18N2O3	F(000) = 632
Mr = 298.33	Dx = 1.292 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 117 reflections
a = 8.4061 (8) Å	θ = 6–20°
b = 11.2568 (5) Å	µ = 0.09 mm^−1
c = 16.4145 (16) Å	T = 200 K
β = 98.988 (8)°	Prism, colourless
V = 1534.2 (2) Å^3	0.22 × 0.18 × 0.13 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	3829 independent reflections
Radiation source: fine-focus sealed tube	2752 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 9 pixels mm^-1	θmax = 28.5°, θmin = 3.6°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −15→15
Tmin = 0.981, Tmax = 0.988	l = −22→21
35768 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.3845P] where P = (Fo^2 + 2Fc^2)/3
3829 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.38697 (14)	0.26077 (9)	0.65758 (6)	0.0437 (3)
O2	0.86553 (11)	0.07956 (9)	0.42532 (6)	0.0392 (3)
O3	0.83793 (11)	0.24633 (9)	0.60472 (6)	0.0367 (3)
N1	0.36411 (12)	0.24204 (9)	0.50114 (6)	0.0265 (3)
N2	0.65482 (12)	0.14390 (9)	0.48630 (6)	0.0245 (3)
C1	0.33574 (15)	0.37372 (11)	0.64393 (8)	0.0279 (3)
C2	0.31560 (16)	0.44167 (12)	0.71259 (8)	0.0329 (4)
C3	0.26040 (18)	0.55646 (12)	0.70294 (9)	0.0385 (4)
C4	0.2252 (2)	0.60576 (14)	0.62526 (10)	0.0528 (6)
C5	0.2461 (2)	0.53965 (13)	0.55684 (9)	0.0447 (5)
C6	0.30137 (15)	0.42201 (11)	0.56370 (7)	0.0277 (3)
C7	0.31783 (15)	0.35103 (11)	0.48987 (7)	0.0271 (3)
C8	0.2818 (2)	0.40854 (13)	0.40636 (8)	0.0438 (5)
C9	0.37200 (14)	0.16073 (11)	0.43574 (7)	0.0250 (3)
C10	0.23477 (15)	0.12373 (12)	0.38351 (8)	0.0324 (4)
C11	0.24396 (16)	0.03598 (13)	0.32547 (8)	0.0346 (4)
C12	0.39076 (17)	−0.01639 (12)	0.31929 (8)	0.0317 (4)
C13	0.52882 (15)	0.01923 (11)	0.37099 (7)	0.0268 (3)
C14	0.52055 (14)	0.10719 (10)	0.42966 (7)	0.0230 (3)
C15	0.81256 (14)	0.12812 (11)	0.48183 (8)	0.0264 (3)
C16	0.92509 (15)	0.17935 (12)	0.55424 (8)	0.0323 (4)
C17	0.9274 (2)	0.27786 (17)	0.68146 (11)	0.0571 (6)
HO1	0.386 (2)	0.2308 (16)	0.6071 (12)	0.061 (5)*
H2	0.33960	0.40910	0.76520	0.0390*
HN1	0.6372 (17)	0.1835 (13)	0.5286 (9)	0.030 (4)*
H3	0.24670	0.60120	0.74900	0.0460*
H4	0.18740	0.68340	0.61900	0.0630*
H5	0.22290	0.57410	0.50480	0.0540*
H8A	0.31510	0.35680	0.36570	0.0660*
H8B	0.33900	0.48240	0.40700	0.0660*
H8C	0.16820	0.42320	0.39300	0.0660*
H10	0.13580	0.15830	0.38760	0.0390*
H11	0.15160	0.01210	0.29060	0.0410*
H12	0.39660	−0.07560	0.28030	0.0380*
H13	0.62730	−0.01580	0.36640	0.0320*
H16A	0.98160	0.11540	0.58620	0.0390*
H16B	1.00440	0.22960	0.53420	0.0390*
H17A	0.97260	0.20770	0.70920	0.0860*
H17B	0.85800	0.31640	0.71450	0.0860*
H17C	1.01260	0.33100	0.67300	0.0860*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0692 (7)	0.0355 (5)	0.0276 (5)	0.0188 (5)	0.0114 (5)	0.0043 (4)
O2	0.0296 (5)	0.0552 (6)	0.0349 (5)	0.0067 (4)	0.0116 (4)	−0.0097 (5)
O3	0.0303 (5)	0.0412 (5)	0.0378 (5)	0.0025 (4)	0.0030 (4)	−0.0139 (4)
N1	0.0239 (5)	0.0313 (6)	0.0255 (5)	0.0042 (4)	0.0076 (4)	−0.0011 (4)
N2	0.0235 (5)	0.0273 (5)	0.0239 (5)	0.0010 (4)	0.0071 (4)	−0.0042 (4)
C1	0.0280 (6)	0.0275 (6)	0.0292 (6)	0.0000 (5)	0.0077 (5)	0.0014 (5)
C2	0.0374 (7)	0.0363 (7)	0.0258 (6)	−0.0045 (6)	0.0076 (5)	−0.0015 (5)
C3	0.0500 (8)	0.0310 (7)	0.0386 (8)	−0.0077 (6)	0.0199 (6)	−0.0099 (6)
C4	0.0867 (13)	0.0264 (7)	0.0508 (9)	0.0102 (7)	0.0275 (9)	0.0020 (7)
C5	0.0708 (11)	0.0308 (7)	0.0354 (8)	0.0116 (7)	0.0176 (7)	0.0069 (6)
C6	0.0283 (6)	0.0279 (6)	0.0282 (6)	0.0009 (5)	0.0089 (5)	0.0017 (5)
C7	0.0252 (6)	0.0308 (6)	0.0265 (6)	0.0016 (5)	0.0076 (5)	0.0025 (5)
C8	0.0662 (10)	0.0382 (8)	0.0279 (7)	0.0095 (7)	0.0105 (7)	0.0051 (6)
C9	0.0274 (6)	0.0271 (6)	0.0219 (6)	0.0012 (5)	0.0079 (5)	0.0022 (5)
C10	0.0242 (6)	0.0405 (7)	0.0329 (7)	0.0016 (5)	0.0058 (5)	0.0022 (6)
C11	0.0319 (7)	0.0410 (7)	0.0295 (7)	−0.0069 (6)	0.0008 (5)	−0.0009 (6)
C12	0.0412 (7)	0.0298 (6)	0.0242 (6)	−0.0034 (6)	0.0055 (5)	−0.0030 (5)
C13	0.0317 (6)	0.0261 (6)	0.0241 (6)	0.0021 (5)	0.0092 (5)	0.0008 (5)
C14	0.0253 (6)	0.0238 (6)	0.0207 (5)	−0.0009 (5)	0.0065 (4)	0.0033 (4)
C15	0.0247 (6)	0.0267 (6)	0.0287 (6)	0.0029 (5)	0.0072 (5)	0.0028 (5)
C16	0.0247 (6)	0.0364 (7)	0.0363 (7)	0.0004 (5)	0.0061 (5)	−0.0041 (6)
C17	0.0466 (9)	0.0687 (12)	0.0525 (10)	0.0002 (8)	−0.0036 (8)	−0.0286 (9)

Geometric parameters (Å, º)

O1—C1	1.3499 (16)	C11—C12	1.386 (2)
O2—C15	1.2192 (16)	C12—C13	1.3857 (19)
O3—C16	1.4077 (16)	C13—C14	1.3905 (16)
O3—C17	1.408 (2)	C15—C16	1.5129 (18)
O1—HO1	0.894 (19)	C2—H2	0.9300
N1—C7	1.2916 (16)	C3—H3	0.9300
N1—C9	1.4202 (15)	C4—H4	0.9300
N2—C14	1.4076 (15)	C5—H5	0.9300
N2—C15	1.3511 (16)	C8—H8A	0.9600
N2—HN1	0.857 (15)	C8—H8B	0.9600
C1—C6	1.4122 (17)	C8—H8C	0.9600
C1—C2	1.3941 (18)	C10—H10	0.9300
C2—C3	1.3737 (19)	C11—H11	0.9300
C3—C4	1.380 (2)	C12—H12	0.9300
C4—C5	1.381 (2)	C13—H13	0.9300
C5—C6	1.4021 (19)	C16—H16A	0.9700
C6—C7	1.4760 (17)	C16—H16B	0.9700
C7—C8	1.5034 (18)	C17—H17A	0.9600
C9—C14	1.4041 (17)	C17—H17B	0.9600
C9—C10	1.3893 (18)	C17—H17C	0.9600
C10—C11	1.3829 (19)
O1···N1	2.5537 (14)	C11···H17B^viii	2.7500
O1···C12^i	3.3138 (18)	C11···H16A^i	3.0800
O1···C13^i	3.2801 (16)	C12···H17B^viii	2.8200
O2···C13	2.9119 (16)	C13···HO1^i	2.913 (18)
O2···C16^ii	3.3941 (17)	C15···H13	2.7800
O2···C10^iii	3.3193 (16)	C15···H4^vi	2.6900
O3···N2	2.5578 (14)	HO1···N1	1.725 (19)
O1···H3^iv	2.7200	HO1···C7	2.349 (19)
O1···H13^i	2.7900	HO1···C9	2.906 (19)
O1···H12^i	2.8500	HO1···C13^i	2.913 (18)
O2···H13	2.3400	HO1···H13^i	2.4600
O2···H10^iii	2.6000	H2···O2^xi	2.6100
O2···H16A^ii	2.5700	HN1···O3	2.062 (15)
O2···H2^v	2.6100	HN1···N1	2.363 (15)
O2···H4^vi	2.7800	H3···O1^xii	2.7200
O3···HN1	2.062 (15)	H3···H13^xi	2.5000
O3···H5^vi	2.7000	H4···O2^vi	2.7800
N1···O1	2.5537 (14)	H4···C15^vi	2.6900
N1···N2	2.7272 (15)	H5···C8	2.5700
N2···N1	2.7272 (15)	H5···H8B	2.2500
N2···O3	2.5578 (14)	H5···H8C	2.4900
N1···HN1	2.363 (15)	H5···O3^vi	2.7000
N1···HO1	1.725 (19)	H8A···C9	2.5000
C4···C15^vi	3.463 (2)	H8A···C10	2.7400
C8···C10	3.245 (2)	H8B···C5	2.7700
C10···C8	3.245 (2)	H8B···H5	2.2500
C10···O2^vii	3.3193 (16)	H8C···C5	2.9700
C11···C16^i	3.5595 (19)	H8C···H5	2.4900
C12···O1^i	3.3138 (18)	H10···O2^vii	2.6000
C12···C17^viii	3.555 (2)	H10···C7	3.0100
C13···O2	2.9119 (16)	H10···C8	3.0700
C13···O1^i	3.2801 (16)	H11···C2^viii	2.9600
C14···C14^i	3.3948 (16)	H12···O1^i	2.8500
C15···C4^vi	3.463 (2)	H13···O2	2.3400
C16···O2^ii	3.3941 (17)	H13···C15	2.7800
C16···C11^i	3.5595 (19)	H13···O1^i	2.7900
C17···C12^ix	3.555 (2)	H13···HO1^i	2.4600
C1···H17C^vii	2.8700	H13···C3^v	3.1000
C2···H17C^vii	2.8200	H13···H3^v	2.5000
C2···H11^ix	2.9600	H16A···H17A	2.2800
C3···H17A^x	3.0000	H16A···O2^ii	2.5700
C3···H13^xi	3.1000	H16A···C11^i	3.0800
C5···H8C	2.9700	H16B···H17C	2.5400
C5···H8B	2.7700	H17A···H16A	2.2800
C7···HO1	2.349 (19)	H17A···C3^xiii	3.0000
C7···H10	3.0100	H17B···C11^ix	2.7500
C8···H10	3.0700	H17B···C12^ix	2.8200
C8···H5	2.5700	H17C···C1^iii	2.8700
C9···HO1	2.906 (19)	H17C···C2^iii	2.8200
C9···H8A	2.5000	H17C···H16B	2.5400
C10···H8A	2.7400
C16—O3—C17	114.03 (11)	C1—C2—H2	120.00
C1—O1—HO1	104.2 (12)	C3—C2—H2	120.00
C7—N1—C9	123.54 (10)	C2—C3—H3	120.00
C14—N2—C15	128.17 (10)	C4—C3—H3	120.00
C15—N2—HN1	114.1 (10)	C3—C4—H4	120.00
C14—N2—HN1	117.7 (10)	C5—C4—H4	120.00
O1—C1—C6	122.06 (11)	C4—C5—H5	119.00
O1—C1—C2	117.29 (12)	C6—C5—H5	119.00
C2—C1—C6	120.64 (12)	C7—C8—H8A	109.00
C1—C2—C3	120.29 (12)	C7—C8—H8B	110.00
C2—C3—C4	120.31 (13)	C7—C8—H8C	109.00
C3—C4—C5	119.91 (14)	H8A—C8—H8B	109.00
C4—C5—C6	121.75 (13)	H8A—C8—H8C	109.00
C1—C6—C7	121.70 (11)	H8B—C8—H8C	109.00
C1—C6—C5	117.09 (11)	C9—C10—H10	120.00
C5—C6—C7	121.18 (11)	C11—C10—H10	120.00
N1—C7—C6	117.48 (10)	C10—C11—H11	120.00
N1—C7—C8	123.57 (11)	C12—C11—H11	120.00
C6—C7—C8	118.96 (11)	C11—C12—H12	120.00
C10—C9—C14	119.30 (11)	C13—C12—H12	120.00
N1—C9—C14	118.52 (10)	C12—C13—H13	120.00
N1—C9—C10	121.83 (11)	C14—C13—H13	120.00
C9—C10—C11	120.59 (12)	O3—C16—H16A	110.00
C10—C11—C12	120.04 (12)	O3—C16—H16B	110.00
C11—C12—C13	120.16 (12)	C15—C16—H16A	110.00
C12—C13—C14	120.17 (12)	C15—C16—H16B	110.00
C9—C14—C13	119.74 (11)	H16A—C16—H16B	108.00
N2—C14—C9	117.21 (10)	O3—C17—H17A	109.00
N2—C14—C13	123.01 (11)	O3—C17—H17B	109.00
O2—C15—N2	125.34 (12)	O3—C17—H17C	110.00
O2—C15—C16	120.72 (11)	H17A—C17—H17B	110.00
N2—C15—C16	113.94 (11)	H17A—C17—H17C	109.00
O3—C16—C15	110.34 (10)	H17B—C17—H17C	109.00
C17—O3—C16—C15	168.27 (12)	C4—C5—C6—C7	177.87 (14)
C9—N1—C7—C6	174.48 (11)	C5—C6—C7—N1	−177.62 (13)
C9—N1—C7—C8	−6.1 (2)	C1—C6—C7—C8	−179.04 (13)
C7—N1—C9—C14	121.72 (13)	C1—C6—C7—N1	0.45 (18)
C7—N1—C9—C10	−65.16 (17)	C5—C6—C7—C8	2.9 (2)
C14—N2—C15—C16	−179.91 (11)	C14—C9—C10—C11	−0.65 (19)
C14—N2—C15—O2	1.3 (2)	N1—C9—C14—C13	174.11 (11)
C15—N2—C14—C9	−163.09 (12)	N1—C9—C10—C11	−173.72 (12)
C15—N2—C14—C13	18.93 (19)	C10—C9—C14—N2	−177.24 (11)
C2—C1—C6—C7	−178.46 (12)	C10—C9—C14—C13	0.81 (18)
C2—C1—C6—C5	−0.31 (19)	N1—C9—C14—N2	−3.95 (16)
O1—C1—C6—C7	0.7 (2)	C9—C10—C11—C12	0.4 (2)
O1—C1—C6—C5	178.85 (13)	C10—C11—C12—C13	−0.2 (2)
O1—C1—C2—C3	−178.57 (13)	C11—C12—C13—C14	0.39 (19)
C6—C1—C2—C3	0.6 (2)	C12—C13—C14—N2	177.25 (11)
C1—C2—C3—C4	−0.3 (2)	C12—C13—C14—C9	−0.69 (18)
C2—C3—C4—C5	−0.3 (2)	O2—C15—C16—O3	170.90 (12)
C3—C4—C5—C6	0.6 (3)	N2—C15—C16—O3	−7.92 (15)
C4—C5—C6—C1	−0.3 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z+1; (iii) x+1, y, z; (iv) −x+1/2, y−1/2, −z+3/2; (v) x+1/2, −y+1/2, z−1/2; (vi) −x+1, −y+1, −z+1; (vii) x−1, y, z; (viii) x−1/2, −y+1/2, z−1/2; (ix) x+1/2, −y+1/2, z+1/2; (x) −x+3/2, y+1/2, −z+3/2; (xi) x−1/2, −y+1/2, z+1/2; (xii) −x+1/2, y+1/2, −z+3/2; (xiii) −x+3/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···N1	0.894 (19)	1.725 (19)	2.5537 (14)	153.1 (17)
N2—HN1···O3	0.857 (15)	2.062 (15)	2.5578 (14)	116.2 (12)
N2—HN1···N1	0.857 (15)	2.363 (15)	2.7272 (15)	106.0 (11)
C13—H13···O2	0.93	2.34	2.9119 (16)	119
C16—H16A···O2^ii	0.97	2.57	3.3941 (17)	143

Symmetry code: (ii) −x+2, −y, −z+1.