(E)-N′-[(Furan-2-yl)methyl­ene]-2-hydroxy-2,2-diphenyl­acetohydrazide monohydrate

Khanfar, M.A.; Abu-Safieh, K.A.; Al-Far, R.; Ali, B.F.; Maichle-Moessmer, C.

doi:10.1107/S1600536807044443

(E)-N′-[(Furan-2-yl)methylene]-2-hydroxy-2,2-diphenylacetohydrazide monohydrate

M. A. Khanfar, K. A. Abu-Safieh, R. Al-Far, B. F. Ali and C. Maichle-Moessmer

In the structure of the title compound, C₁₉H₁₆N₂O₃·H₂O, the configuration with respect to the C=N double bond is trans. The molecules form layers parallel to the ac plane, linked to each other by water molecules and OH groups, which are extended along the b axis involving the NH groups of adjacent molecules via N—H

OH₂ interactions, thus resulting in sheets of molecules. In addition, there are edge-to-face and offset face-to-face interactions between phenyl rings of adjacent molecules along both the a and b axes [C

C distances in the range 3.9–4.1 Å]. The extremely strong hydrogen bonds and phenyl–phenyl interactions contribute greatly to stabilizing the three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044443/pv2031sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044443/pv2031Isup2.hkl Contains datablock I

CCDC reference: 663782

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Key indicators

Single-crystal X-ray study
T = 213 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.123
Data-to-parameter ratio = 11.1

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Alert level G
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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Comment top

Schiff base hydrazones derived from the condensation of aromatic carbaldehydes and hydrazides are of interest owing to their biological activities and applications (Sun et al., 2006; Gup & Kirkan, 2005; Ganjali et al., 2006; Getautis et al., 2006). They have been also used as multidentate ligands for complexation with metal ions (Kuriakose et al., 2007). On the other hand, research in the field of supramolecular complexes containing metal ions and aroylhdrazones is of a considerable interest due to their possible applications as molecule-based metals and magnets, optical and thermal switches, and probes for DNA structurs (Owen & Wenbin, 2002; Tobin, 1990). The crystal structure of the title compound is reported here.

The asymmetric unit of the title compound comprises an organic moiety and a water of solvation (Fig. 1). Bond distances and angles, are within normal ranges (Allen et al., 1987), and in accordance with those reported for similar compounds (Yathirajan et al., 2007; Mathew et al., 2007; Sun et al., 2007). The existance of organic moiety in the title compound in the expected keto form is evident from the C6—O2 bond length, and the C5=N1 bond length confirms the double bond character. The C6–N2 bond length is typical for an intermediate between a single and a double bond, suggesting some degree of delocalization in the hydrazide.

The molecules are packed efficiently in a layer motif running parallel to the c axis, Fig. 2. In this arrangement, the molecules are linked to each other by water molecules that involve in multihydrogen bonding with the organic moiety. Its two H atoms engage each in binding to one O and one N atoms simultyaneouly (Fig. 1) as O—H···N, O—H···O and O—H···O, forming a double bifurcated hydrogen bonds. The water molecules further interact with the OH groups from the next organic molecule parallel to c axis (Fig. 2). These hydrogen bonds are extremely strong (Table 1) as is evident by relatively short D···A distances and D—H···A angles. There is a strong intramolecular interaction N2—H2A···O3 in the structure. In addition to the hydrogen bonding, molecules within layers exhibit via phenyl···phenyl (Ph···Ph) interactions (Dance 1996) in an edge-to-face ef motif (C—H···π; C12—H12···C17, C18 (x, 1/2 - y, 1/2 + z) of the order of 2.969 and 2.978 Å, respectively). The Ph···Ph interactions, using the diphenyl groups, between each layer and the adjacent one parallel to the a axis also exist comprising both offset-to-face (off) and edge-to-face (ef) motifs (C···C distances in the range 3.9 - 4.1 Å), Fig. 2.

Ph···Ph interactions together with the extremely strong hydrogen bonds contribute greatly in stabilization of a three-dimensional network.

Related literature top

For general backgroud, see: Sun et al. (2006); Gup & Kirkan (2005); Ganjali et al. (2006); Getautis et al. (2006); Kuriakose et al. (2007); Owen & Wenbin (2002); Tobin (1990). For related literature, see: (Allen et al. (1987); Yathirajan et al. (2007); Mathew et al. (2007); Sun et al. (2007); Dance (1996).

Experimental top

For the preparation of the title compound, a mixture of 2-hydroxy-2,2-diphenylacetohydrazide (240 mg, 1 mmol) and furan-2-carbaldehyde (110 mg, 1.1 mmol) dissolved in propanol (25 ml), was refluxed with stirring for 3 h. The resulting mixture was filtered off and allowed to stand undisturbed at room temperature. The title compound crystallized out during few days as colourless plates. Crystals were filtered off, washed with 20 ml cold methanol then 10 ml diethylether, and dried under vacuum (yield: 89%). Solid; mp 451–452 K; Spectroscopic analysis: IR (KBr, ν cm^-1): 3280; νNH, 1667; νC=O, 1625; νC=N; ¹H NMR (300 MHz, DMSO, δ, p.p.m.): 3.50 (s, OH); 9.9 (s, CONH); 9.30 (s,CH=); 7.10 - 7.40 (m, ArH); 7.70–7.90 (m, R); EIMS: m/z = 320 (M+).

Structure description top

Ph···Ph interactions together with the extremely strong hydrogen bonds contribute greatly in stabilization of a three-dimensional network.

Computing details top

Data collection: CAD-4 (Enraf–Nonius, 1994); cell refinement: SET4 and CELDIM (Enraf–Nonius, 1994); data reduction: HELENA (Spek, 1996) and PLATON (Spek, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound showing the layers of molecules; hydrogen atoms not involved in hydrogen bonding were omitted for clarity. Hydrogen bonds and Ph···Ph interactions are shown with dashed and solid lines, respectively.

(E)—N'-[(furan-2-yl)methylene]-2-hydroxy-2,2- diphenylacetohydrazide monohydrate top

Crystal data top

C₁₉H₁₆N₂O₃·H₂O	F(000) = 712
M_r = 338.35	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.6339 (17) Å	θ = 2.1–27.4°
b = 10.857 (2) Å	µ = 0.10 mm⁻¹
c = 14.5207 (12) Å	T = 213 K
β = 91.819 (10)°	Plate, colorless
V = 1675.6 (4) Å³	0.55 × 0.50 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1981 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 26.1°, θ_min = 3.1°
ω scans	h = −1→13
Absorption correction: ψ scan (program; reference?)	k = 0→13
T_min = 0.937, T_max = 0.985	l = −17→17
3847 measured reflections	3 standard reflections every 400 reflections
3293 independent reflections	intensity decay: 3.0%

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.0534P)² + 0.0604P] where P = (F_o² + 2F_c²)/3
3293 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₃·H₂O	V = 1675.6 (4) Å³
M_r = 338.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6339 (17) Å	µ = 0.10 mm⁻¹
b = 10.857 (2) Å	T = 213 K
c = 14.5207 (12) Å	0.55 × 0.50 × 0.20 mm
β = 91.819 (10)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1981 reflections with I > 2σ(I)
Absorption correction: ψ scan (program; reference?)	R_int = 0.054
T_min = 0.937, T_max = 0.985	3 standard reflections every 400 reflections
3847 measured reflections	intensity decay: 3.0%
3293 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.123	All H-atom parameters refined
S = 1.01	Δρ_max = 0.17 e Å⁻³
3293 reflections	Δρ_min = −0.20 e Å⁻³
298 parameters

Special details top

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 taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.1720 (2)	0.2889 (2)	0.13010 (15)	0.0332 (5)
O1	1.14268 (15)	0.18466 (15)	0.07977 (11)	0.0413 (4)
C4	1.2148 (3)	0.1898 (3)	0.00285 (17)	0.0436 (6)
H4	1.201 (2)	0.116 (3)	−0.0400 (18)	0.058 (8)*
C3	1.2863 (3)	0.2907 (3)	0.00473 (17)	0.0444 (6)
H3	1.346 (2)	0.316 (2)	−0.0402 (19)	0.058 (8)*
C2	1.2589 (2)	0.3555 (3)	0.08660 (18)	0.0413 (6)
H2	1.288 (2)	0.432 (3)	0.1031 (18)	0.053 (8)*
C5	1.1047 (2)	0.3121 (2)	0.21232 (16)	0.0346 (5)
H5	1.124 (2)	0.390 (2)	0.2423 (15)	0.038 (6)*
N1	1.02022 (17)	0.23747 (18)	0.23979 (12)	0.0347 (5)
N2	0.95604 (18)	0.2774 (2)	0.31553 (13)	0.0341 (5)
H2A	0.978 (2)	0.347 (2)	0.3437 (16)	0.037 (7)*
O2	0.81756 (15)	0.11956 (15)	0.30338 (11)	0.0408 (4)
C6	0.8530 (2)	0.2155 (2)	0.34018 (14)	0.0311 (5)
C7	0.7808 (2)	0.2756 (2)	0.41943 (15)	0.0330 (5)
O3	0.85302 (15)	0.38056 (15)	0.44913 (12)	0.0368 (4)
H3A	0.851 (3)	0.390 (3)	0.512 (2)	0.084 (11)*
C8	0.7711 (2)	0.1843 (2)	0.49953 (14)	0.0336 (5)
C9	0.8780 (3)	0.1208 (2)	0.52946 (17)	0.0413 (6)
H9	0.955 (2)	0.130 (2)	0.4964 (17)	0.049 (7)*
C10	0.8751 (3)	0.0443 (2)	0.60630 (17)	0.0472 (7)
H10	0.953 (3)	−0.001 (3)	0.6239 (18)	0.055 (8)*
C11	0.7665 (3)	0.0320 (3)	0.65384 (18)	0.0526 (8)
H11	0.762 (2)	−0.023 (2)	0.708 (2)	0.061 (8)*
C12	0.6610 (3)	0.0944 (3)	0.6250 (2)	0.0588 (8)
H12	0.584 (3)	0.088 (3)	0.652 (2)	0.070 (9)*
C13	0.6619 (3)	0.1708 (3)	0.54799 (18)	0.0480 (7)
H13	0.586 (2)	0.213 (2)	0.5267 (18)	0.053 (8)*
C14	0.6519 (2)	0.3186 (2)	0.38027 (14)	0.0331 (5)
C19	0.5693 (2)	0.2389 (3)	0.33438 (17)	0.0425 (6)
H19	0.593 (2)	0.155 (3)	0.3246 (18)	0.048 (8)*
C18	0.4533 (3)	0.2802 (3)	0.30040 (19)	0.0504 (7)
H18	0.400 (3)	0.226 (2)	0.2699 (18)	0.054 (8)*
C17	0.4181 (3)	0.4014 (3)	0.31322 (19)	0.0520 (8)
H17	0.340 (3)	0.429 (3)	0.2918 (18)	0.059 (8)*
C16	0.4982 (3)	0.4808 (3)	0.3585 (2)	0.0538 (7)
H16	0.474 (3)	0.568 (3)	0.3693 (19)	0.063 (8)*
C15	0.6151 (3)	0.4395 (3)	0.39158 (18)	0.0456 (7)
H15	0.669 (3)	0.496 (2)	0.4232 (19)	0.055 (8)*
O4	0.9139 (2)	0.03785 (18)	0.12617 (13)	0.0501 (5)
H4"	0.892 (4)	0.079 (4)	0.174 (3)	0.137 (18)*
H4'	0.997 (4)	0.071 (4)	0.116 (3)	0.123 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0347 (13)	0.0348 (13)	0.0300 (12)	0.0010 (11)	0.0006 (10)	−0.0048 (11)
O1	0.0487 (10)	0.0379 (9)	0.0380 (9)	−0.0019 (8)	0.0098 (8)	−0.0047 (8)
C4	0.0563 (16)	0.0442 (15)	0.0309 (13)	0.0065 (14)	0.0097 (12)	−0.0021 (12)
C3	0.0478 (15)	0.0518 (17)	0.0343 (13)	0.0051 (14)	0.0122 (12)	0.0069 (13)
C2	0.0453 (16)	0.0393 (15)	0.0398 (15)	−0.0069 (12)	0.0072 (12)	−0.0003 (12)
C5	0.0348 (13)	0.0373 (14)	0.0318 (12)	−0.0024 (12)	0.0018 (10)	−0.0052 (11)
N1	0.0372 (11)	0.0400 (11)	0.0270 (10)	0.0027 (9)	0.0053 (8)	−0.0032 (9)
N2	0.0386 (11)	0.0366 (11)	0.0276 (10)	−0.0036 (10)	0.0070 (8)	−0.0069 (9)
O2	0.0500 (10)	0.0373 (10)	0.0357 (9)	−0.0073 (8)	0.0091 (8)	−0.0073 (8)
C6	0.0359 (13)	0.0333 (13)	0.0241 (11)	−0.0002 (11)	−0.0002 (9)	0.0003 (10)
C7	0.0370 (13)	0.0336 (13)	0.0284 (12)	−0.0031 (11)	0.0011 (10)	−0.0039 (10)
O3	0.0439 (10)	0.0381 (9)	0.0285 (9)	−0.0079 (8)	0.0031 (8)	−0.0063 (8)
C8	0.0405 (13)	0.0373 (13)	0.0230 (11)	−0.0031 (11)	0.0017 (10)	−0.0040 (10)
C9	0.0421 (15)	0.0484 (16)	0.0332 (13)	−0.0046 (13)	−0.0023 (12)	−0.0016 (12)
C10	0.0601 (18)	0.0457 (16)	0.0353 (14)	−0.0015 (15)	−0.0073 (13)	0.0006 (12)
C11	0.081 (2)	0.0479 (17)	0.0291 (14)	−0.0066 (16)	0.0059 (14)	0.0025 (13)
C12	0.065 (2)	0.069 (2)	0.0439 (17)	−0.0013 (17)	0.0223 (15)	0.0081 (15)
C13	0.0477 (16)	0.0589 (18)	0.0380 (14)	0.0064 (14)	0.0117 (13)	0.0048 (13)
C14	0.0365 (12)	0.0414 (14)	0.0216 (11)	−0.0010 (11)	0.0056 (10)	0.0013 (10)
C19	0.0415 (15)	0.0479 (17)	0.0380 (14)	−0.0075 (13)	−0.0017 (11)	0.0000 (12)
C18	0.0396 (15)	0.069 (2)	0.0418 (15)	−0.0119 (15)	−0.0047 (12)	0.0025 (15)
C17	0.0400 (16)	0.077 (2)	0.0396 (15)	0.0099 (16)	0.0021 (13)	0.0074 (15)
C16	0.0537 (18)	0.057 (2)	0.0507 (16)	0.0158 (15)	0.0037 (14)	−0.0042 (15)
C15	0.0490 (16)	0.0456 (16)	0.0421 (14)	0.0016 (14)	−0.0013 (13)	−0.0090 (13)
O4	0.0717 (14)	0.0477 (12)	0.0309 (10)	−0.0153 (10)	0.0000 (9)	−0.0013 (9)

Geometric parameters (Å, º) top

C1—C2	1.347 (3)	C9—C10	1.392 (4)
C1—O1	1.377 (3)	C9—H9	0.97 (3)
C1—C5	1.434 (3)	C10—C11	1.370 (4)
O1—C4	1.376 (3)	C10—H10	0.99 (3)
C4—C3	1.333 (4)	C11—C12	1.365 (4)
C4—H4	1.02 (3)	C11—H11	0.98 (3)
C3—C2	1.420 (4)	C12—C13	1.393 (4)
C3—H3	0.96 (3)	C12—H12	0.92 (3)
C2—H2	0.91 (3)	C13—H13	0.97 (3)
C5—N1	1.282 (3)	C14—C15	1.381 (3)
C5—H5	0.97 (2)	C14—C19	1.389 (3)
N1—N2	1.382 (3)	C19—C18	1.388 (4)
N2—C6	1.343 (3)	C19—H19	0.95 (3)
N2—H2A	0.89 (2)	C18—C17	1.381 (4)
O2—C6	1.225 (3)	C18—H18	0.92 (3)
C6—C7	1.548 (3)	C17—C16	1.366 (4)
C7—O3	1.433 (3)	C17—H17	0.93 (3)
C7—C8	1.534 (3)	C16—C15	1.392 (4)
C7—C14	1.539 (3)	C16—H16	1.00 (3)
O3—H3A	0.92 (3)	C15—H15	0.94 (3)
C8—C13	1.384 (3)	O4—H4"	0.86 (5)
C8—C9	1.388 (3)	O4—H4'	0.97 (5)

C2—C1—O1	109.8 (2)	C8—C9—H9	119.6 (15)
C2—C1—C5	131.6 (2)	C10—C9—H9	119.8 (15)
O1—C1—C5	118.4 (2)	C11—C10—C9	120.2 (3)
C4—O1—C1	105.93 (19)	C11—C10—H10	122.2 (15)
C3—C4—O1	110.4 (2)	C9—C10—H10	117.7 (16)
C3—C4—H4	136.8 (15)	C12—C11—C10	119.6 (3)
O1—C4—H4	112.8 (15)	C12—C11—H11	118.8 (16)
C4—C3—C2	107.0 (2)	C10—C11—H11	121.5 (16)
C4—C3—H3	127.2 (16)	C11—C12—C13	121.0 (3)
C2—C3—H3	125.8 (16)	C11—C12—H12	124.2 (19)
C1—C2—C3	106.8 (2)	C13—C12—H12	114.7 (19)
C1—C2—H2	126.6 (17)	C8—C13—C12	119.9 (3)
C3—C2—H2	126.3 (17)	C8—C13—H13	119.2 (16)
N1—C5—C1	121.4 (2)	C12—C13—H13	120.9 (16)
N1—C5—H5	123.4 (14)	C15—C14—C19	118.2 (2)
C1—C5—H5	115.0 (14)	C15—C14—C7	119.8 (2)
C5—N1—N2	114.69 (19)	C19—C14—C7	122.0 (2)
C6—N2—N1	118.8 (2)	C18—C19—C14	120.7 (3)
C6—N2—H2A	120.6 (16)	C18—C19—H19	119.2 (16)
N1—N2—H2A	120.3 (16)	C14—C19—H19	120.1 (16)
O2—C6—N2	123.5 (2)	C17—C18—C19	120.1 (3)
O2—C6—C7	122.0 (2)	C17—C18—H18	120.7 (17)
N2—C6—C7	114.5 (2)	C19—C18—H18	119.2 (17)
O3—C7—C8	109.50 (17)	C16—C17—C18	119.9 (3)
O3—C7—C14	109.42 (18)	C16—C17—H17	119.7 (17)
C8—C7—C14	113.30 (18)	C18—C17—H17	120.4 (17)
O3—C7—C6	106.54 (18)	C17—C16—C15	120.0 (3)
C8—C7—C6	109.77 (18)	C17—C16—H16	120.9 (16)
C14—C7—C6	108.08 (17)	C15—C16—H16	119.2 (16)
C7—O3—H3A	111 (2)	C14—C15—C16	121.2 (3)
C13—C8—C9	118.7 (2)	C14—C15—H15	120.0 (16)
C13—C8—C7	122.1 (2)	C16—C15—H15	118.8 (16)
C9—C8—C7	119.0 (2)	H4"—O4—H4'	102 (4)
C8—C9—C10	120.6 (3)

C2—C1—O1—C4	−0.3 (3)	C6—C7—C8—C9	47.0 (3)
C5—C1—O1—C4	176.3 (2)	C13—C8—C9—C10	0.5 (4)
C1—O1—C4—C3	0.5 (3)	C7—C8—C9—C10	175.1 (2)
O1—C4—C3—C2	−0.5 (3)	C8—C9—C10—C11	−0.6 (4)
O1—C1—C2—C3	0.0 (3)	C9—C10—C11—C12	0.5 (4)
C5—C1—C2—C3	−176.0 (2)	C10—C11—C12—C13	−0.1 (4)
C4—C3—C2—C1	0.4 (3)	C9—C8—C13—C12	−0.1 (4)
C2—C1—C5—N1	176.7 (3)	C7—C8—C13—C12	−174.6 (2)
O1—C1—C5—N1	1.0 (3)	C11—C12—C13—C8	−0.1 (4)
C1—C5—N1—N2	−174.7 (2)	O3—C7—C14—C15	−10.3 (3)
C5—N1—N2—C6	169.5 (2)	C8—C7—C14—C15	112.2 (2)
N1—N2—C6—O2	5.7 (3)	C6—C7—C14—C15	−125.9 (2)
N1—N2—C6—C7	−174.00 (18)	O3—C7—C14—C19	170.6 (2)
O2—C6—C7—O3	176.32 (19)	C8—C7—C14—C19	−66.9 (3)
N2—C6—C7—O3	−4.0 (3)	C6—C7—C14—C19	55.0 (3)
O2—C6—C7—C8	57.9 (3)	C15—C14—C19—C18	0.4 (4)
N2—C6—C7—C8	−122.5 (2)	C7—C14—C19—C18	179.5 (2)
O2—C6—C7—C14	−66.2 (3)	C14—C19—C18—C17	−1.0 (4)
N2—C6—C7—C14	113.5 (2)	C19—C18—C17—C16	0.7 (4)
O3—C7—C8—C13	104.8 (2)	C18—C17—C16—C15	0.1 (4)
C14—C7—C8—C13	−17.6 (3)	C19—C14—C15—C16	0.4 (4)
C6—C7—C8—C13	−138.6 (2)	C7—C14—C15—C16	−178.8 (2)
O3—C7—C8—C9	−69.7 (3)	C17—C16—C15—C14	−0.6 (4)
C14—C7—C8—C9	167.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.89 (2)	2.40 (2)	3.248 (3)	159 (2)
O3—H3A···O4ⁱⁱ	0.92 (3)	1.94 (3)	2.776 (2)	151 (3)
O4—H4′′···O2	0.86 (5)	2.11 (5)	2.937 (3)	161 (4)
O4—H4′′···N1	0.86 (5)	2.38 (5)	2.929 (3)	122 (4)
O4—H4′···O1	0.97 (5)	2.07 (5)	3.003 (3)	163 (4)
O4—H4′···N1	0.97 (5)	2.56 (5)	2.929 (3)	103 (4)
N2—H2A···O3	0.89 (2)	2.09 (2)	2.521 (3)	109 (2)

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₃·H₂O
M_r	338.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	213
a, b, c (Å)	10.6339 (17), 10.857 (2), 14.5207 (12)
β (°)	91.819 (10)
V (Å³)	1675.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.55 × 0.50 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (program; reference?)
T_min, T_max	0.937, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	3847, 3293, 1981
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.123, 1.01
No. of reflections	3293
No. of parameters	298
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: CAD-4 (Enraf–Nonius, 1994), SET4 and CELDIM (Enraf–Nonius, 1994), HELENA (Spek, 1996) and PLATON (Spek, 2003), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), PLATON (Spek, 2003), XCIF in SHELXTL (Sheldrick, 1997b).