(E)-2-{4-[1-(Hydroxyimino)ethyl]phenyl-iminomethyl}-6-methoxyphenol mono-hydrate.

In the title compound, C(16)H(16)N(2)O(3)·H(2)O, the benzene rings are nearly coplanar with each other, forming a dihedral angle of 4.46 (3)°. There is a strong intra-molecular O-H⋯N hydrogen bond which results in a six-membered ring. In the crystal, the mol-ecules are connected into a three-dimensional network via O-H⋯O and O-H⋯N inter-molecular hydrogen bonds, forming a centrosymmetric ring along the b axis with graph-set motif R(4) (4)(10). In addition, the short distances between the centroids of six-membered rings [3.555 (1) Å], indicate the existence of π-π stacking inter-actions, which may stabilize the crystal structure.

Related literature

For background to oximes, see: Chaudhuri (2003 ▶); Dong et al. (2008 ▶, 2009 ▶); Zhao et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H16N2O3·H2O

M = 302.32

Triclinic,

a = 8.1030 (14) Å

b = 8.3273 (15) Å

c = 12.4392 (16) Å

α = 72.095 (1)°

β = 80.012 (2)°

γ = 69.454 (1)°

V = 745.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.45 × 0.33 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.987

3912 measured reflections

2586 independent reflections

1202 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.149

S = 1.02

2586 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042032/pv2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042032/pv2215Isup2.hkl

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

C16H16N2O3·H2O	Z = 2
Mr = 302.32	F(000) = 320
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Melting point = 462–464 K
a = 8.1030 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3273 (15) Å	Cell parameters from 714 reflections
c = 12.4392 (16) Å	θ = 2.7–24.1°
α = 72.095 (1)°	µ = 0.10 mm−1
β = 80.012 (2)°	T = 298 K
γ = 69.454 (1)°	Block-like, red
V = 745.9 (2) Å3	0.45 × 0.33 × 0.13 mm

Bruker SMART 1000 CCD area detector diffractometer	2586 independent reflections
Radiation source: fine-focus sealed tube	1202 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ & ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→9
Tmin = 0.957, Tmax = 0.987	k = −8→9
3912 measured reflections	l = −14→14

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.057P)2] where P = (Fo2 + 2Fc2)/3
2586 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. Yield (164.9 mg) 60.69%. m. p. 462–464 K. Anal. Calcd. for C16H18N2O4: C, 63.56; H, 6.00; N, 9.27. Found: C, 63.40; H, 5.89; N, 9.35.

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.

	x	y	z	Uiso*/Ueq
N1	0.7058 (3)	−0.0828 (3)	0.08266 (19)	0.0465 (7)
N2	0.2416 (3)	0.2204 (3)	0.49248 (18)	0.0434 (7)
O1	0.7764 (3)	−0.1760 (3)	0.00028 (16)	0.0581 (7)
H1	0.8534	−0.1382	−0.0402	0.087*
O2	0.0132 (3)	0.2394 (3)	0.66543 (16)	0.0557 (6)
H2	0.0742	0.1976	0.6145	0.084*
O3	−0.1419 (3)	0.3878 (3)	0.83000 (16)	0.0588 (7)
O4	0.0191 (3)	0.9607 (3)	0.87286 (16)	0.0640 (7)
H4A	−0.0095	1.0490	0.8152	0.077*
H4B	0.0937	0.9763	0.9057	0.077*
C1	0.5205 (4)	−0.2745 (4)	0.1335 (3)	0.0639 (10)
H1A	0.4568	−0.2300	0.0665	0.096*
H1B	0.4444	−0.3084	0.1984	0.096*
H1C	0.6208	−0.3762	0.1267	0.096*
C2	0.5816 (4)	−0.1332 (4)	0.1469 (2)	0.0410 (8)
C3	0.4953 (4)	−0.0402 (4)	0.2358 (2)	0.0398 (8)
C4	0.5415 (4)	0.0994 (5)	0.2463 (3)	0.0587 (10)
H4	0.6288	0.1356	0.1957	0.070*
C5	0.4632 (4)	0.1858 (4)	0.3285 (3)	0.0582 (10)
H5	0.4994	0.2778	0.3329	0.070*
C6	0.3319 (4)	0.1393 (4)	0.4047 (2)	0.0422 (8)
C7	0.2842 (4)	0.0012 (4)	0.3959 (2)	0.0517 (9)
H7	0.1968	−0.0342	0.4468	0.062*
C8	0.3632 (4)	−0.0859 (4)	0.3131 (2)	0.0517 (9)
H8	0.3268	−0.1780	0.3091	0.062*
C9	0.2666 (4)	0.3593 (4)	0.5021 (2)	0.0464 (8)
H9	0.3440	0.4082	0.4491	0.056*
C10	0.1800 (4)	0.4421 (4)	0.5912 (2)	0.0429 (8)
C11	0.0578 (4)	0.3787 (4)	0.6698 (2)	0.0408 (8)
C12	−0.0257 (4)	0.4610 (4)	0.7574 (2)	0.0432 (8)
C13	0.0148 (4)	0.6037 (4)	0.7638 (2)	0.0491 (8)
H13	−0.0385	0.6574	0.8220	0.059*
C14	0.1346 (4)	0.6693 (4)	0.6846 (3)	0.0589 (10)
H14	0.1598	0.7674	0.6894	0.071*
C15	0.2161 (4)	0.5905 (4)	0.5991 (3)	0.0561 (9)
H15	0.2958	0.6359	0.5461	0.067*
C16	−0.2143 (4)	0.4549 (5)	0.9261 (2)	0.0670 (11)
H16A	−0.1202	0.4480	0.9665	0.100*
H16B	−0.2844	0.3853	0.9749	0.100*
H16C	−0.2872	0.5766	0.9017	0.100*

	U11	U22	U33	U12	U13	U23
N1	0.0498 (17)	0.0535 (18)	0.0406 (14)	−0.0166 (14)	0.0027 (13)	−0.0219 (14)
N2	0.0459 (17)	0.0426 (17)	0.0378 (14)	−0.0102 (13)	0.0004 (12)	−0.0117 (13)
O1	0.0661 (16)	0.0676 (17)	0.0528 (13)	−0.0311 (13)	0.0165 (11)	−0.0330 (12)
O2	0.0715 (16)	0.0571 (15)	0.0516 (13)	−0.0332 (13)	0.0125 (11)	−0.0271 (12)
O3	0.0683 (16)	0.0705 (17)	0.0538 (14)	−0.0367 (13)	0.0183 (12)	−0.0349 (13)
O4	0.0766 (17)	0.0707 (17)	0.0532 (13)	−0.0408 (14)	0.0019 (12)	−0.0119 (12)
C1	0.068 (2)	0.067 (3)	0.071 (2)	−0.032 (2)	0.0146 (19)	−0.035 (2)
C2	0.043 (2)	0.043 (2)	0.0394 (18)	−0.0172 (17)	−0.0020 (15)	−0.0110 (15)
C3	0.041 (2)	0.041 (2)	0.0370 (17)	−0.0125 (16)	−0.0042 (14)	−0.0102 (15)
C4	0.061 (2)	0.073 (3)	0.057 (2)	−0.039 (2)	0.0220 (18)	−0.031 (2)
C5	0.054 (2)	0.074 (3)	0.065 (2)	−0.035 (2)	0.0180 (18)	−0.040 (2)
C6	0.044 (2)	0.043 (2)	0.0387 (18)	−0.0133 (17)	−0.0002 (15)	−0.0108 (16)
C7	0.055 (2)	0.048 (2)	0.0474 (19)	−0.0219 (18)	0.0168 (16)	−0.0121 (17)
C8	0.054 (2)	0.047 (2)	0.056 (2)	−0.0234 (18)	0.0096 (17)	−0.0158 (18)
C9	0.044 (2)	0.042 (2)	0.0442 (18)	−0.0100 (17)	0.0051 (15)	−0.0078 (16)
C10	0.040 (2)	0.043 (2)	0.0417 (18)	−0.0108 (17)	−0.0001 (15)	−0.0104 (16)
C11	0.047 (2)	0.038 (2)	0.0411 (18)	−0.0146 (16)	−0.0057 (15)	−0.0128 (15)
C12	0.041 (2)	0.045 (2)	0.0449 (18)	−0.0146 (17)	−0.0033 (15)	−0.0132 (16)
C13	0.052 (2)	0.047 (2)	0.053 (2)	−0.0151 (18)	−0.0034 (17)	−0.0207 (17)
C14	0.065 (2)	0.049 (2)	0.072 (2)	−0.024 (2)	−0.002 (2)	−0.025 (2)
C15	0.060 (2)	0.044 (2)	0.064 (2)	−0.0242 (19)	0.0098 (18)	−0.0135 (18)
C16	0.075 (3)	0.086 (3)	0.052 (2)	−0.034 (2)	0.0175 (18)	−0.036 (2)

N1—C2	1.281 (3)	C5—C6	1.377 (4)
N1—O1	1.398 (3)	C5—H5	0.9300
N2—C9	1.285 (3)	C6—C7	1.375 (4)
N2—C6	1.418 (3)	C7—C8	1.378 (4)
O1—H1	0.8200	C7—H7	0.9300
O2—C11	1.349 (3)	C8—H8	0.9300
O2—H2	0.8200	C9—C10	1.434 (4)
O3—C12	1.357 (3)	C9—H9	0.9300
O3—C16	1.422 (3)	C10—C11	1.388 (4)
O4—H4A	0.8500	C10—C15	1.400 (4)
O4—H4B	0.8500	C11—C12	1.412 (4)
C1—C2	1.489 (4)	C12—C13	1.367 (4)
C1—H1A	0.9600	C13—C14	1.386 (4)
C1—H1B	0.9600	C13—H13	0.9300
C1—H1C	0.9600	C14—C15	1.371 (4)
C2—C3	1.480 (4)	C14—H14	0.9300
C3—C8	1.386 (4)	C15—H15	0.9300
C3—C4	1.388 (4)	C16—H16A	0.9600
C4—C5	1.369 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C2—N1—O1	112.3 (2)	C7—C8—C3	121.9 (3)
C9—N2—C6	121.4 (3)	C7—C8—H8	119.1
N1—O1—H1	109.5	C3—C8—H8	119.1
C11—O2—H2	109.5	N2—C9—C10	122.7 (3)
C12—O3—C16	117.0 (2)	N2—C9—H9	118.6
H4A—O4—H4B	107.7	C10—C9—H9	118.6
C2—C1—H1A	109.5	C11—C10—C15	119.0 (3)
C2—C1—H1B	109.5	C11—C10—C9	120.9 (3)
H1A—C1—H1B	109.5	C15—C10—C9	120.1 (3)
C2—C1—H1C	109.5	O2—C11—C10	122.1 (3)
H1A—C1—H1C	109.5	O2—C11—C12	117.6 (3)
H1B—C1—H1C	109.5	C10—C11—C12	120.2 (3)
N1—C2—C3	116.7 (3)	O3—C12—C13	125.3 (3)
N1—C2—C1	123.0 (3)	O3—C12—C11	115.4 (3)
C3—C2—C1	120.3 (3)	C13—C12—C11	119.3 (3)
C8—C3—C4	115.9 (3)	C12—C13—C14	120.7 (3)
C8—C3—C2	122.4 (3)	C12—C13—H13	119.6
C4—C3—C2	121.8 (3)	C14—C13—H13	119.6
C5—C4—C3	122.3 (3)	C15—C14—C13	120.4 (3)
C5—C4—H4	118.9	C15—C14—H14	119.8
C3—C4—H4	118.9	C13—C14—H14	119.8
C4—C5—C6	121.3 (3)	C14—C15—C10	120.3 (3)
C4—C5—H5	119.4	C14—C15—H15	119.8
C6—C5—H5	119.4	C10—C15—H15	119.8
C7—C6—C5	117.3 (3)	O3—C16—H16A	109.5
C7—C6—N2	116.8 (3)	O3—C16—H16B	109.5
C5—C6—N2	125.9 (3)	H16A—C16—H16B	109.5
C6—C7—C8	121.3 (3)	O3—C16—H16C	109.5
C6—C7—H7	119.3	H16A—C16—H16C	109.5
C8—C7—H7	119.3	H16B—C16—H16C	109.5
O1—N1—C2—C3	−178.9 (2)	N2—C9—C10—C11	−2.6 (4)
O1—N1—C2—C1	−0.4 (4)	N2—C9—C10—C15	178.3 (3)
N1—C2—C3—C8	−177.9 (3)	C15—C10—C11—O2	178.2 (3)
C1—C2—C3—C8	3.6 (4)	C9—C10—C11—O2	−0.9 (4)
N1—C2—C3—C4	2.5 (4)	C15—C10—C11—C12	−1.2 (4)
C1—C2—C3—C4	−176.0 (3)	C9—C10—C11—C12	179.7 (3)
C8—C3—C4—C5	0.7 (5)	C16—O3—C12—C13	−6.2 (4)
C2—C3—C4—C5	−179.7 (3)	C16—O3—C12—C11	173.5 (2)
C3—C4—C5—C6	−0.8 (5)	O2—C11—C12—O3	1.0 (4)
C4—C5—C6—C7	0.8 (5)	C10—C11—C12—O3	−179.6 (2)
C4—C5—C6—N2	−179.6 (3)	O2—C11—C12—C13	−179.3 (3)
C9—N2—C6—C7	−174.4 (3)	C10—C11—C12—C13	0.1 (4)
C9—N2—C6—C5	6.0 (5)	O3—C12—C13—C14	−179.4 (3)
C5—C6—C7—C8	−0.7 (5)	C11—C12—C13—C14	0.9 (5)
N2—C6—C7—C8	179.6 (3)	C12—C13—C14—C15	−0.8 (5)
C6—C7—C8—C3	0.7 (5)	C13—C14—C15—C10	−0.4 (5)
C4—C3—C8—C7	−0.6 (5)	C11—C10—C15—C14	1.4 (5)
C2—C3—C8—C7	179.7 (3)	C9—C10—C15—C14	−179.5 (3)
C6—N2—C9—C10	−178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.84	2.656 (3)	176
O2—H2···N2	0.82	1.86	2.589 (3)	147
O4—H4A···O2ii	0.85	2.07	2.885 (3)	161
O4—H4B···N1iii	0.85	2.15	2.945 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.84	2.656 (3)	176
O2—H2⋯N2	0.82	1.86	2.589 (3)	147
O4—H4A⋯O2ii	0.85	2.07	2.885 (3)	161
O4—H4B⋯N1iii	0.85	2.15	2.945 (3)	156

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