N'-(2-Hydr-oxy-3-methoxy-benzyl-idene)-1,3-benzodioxole-5-carbohydrazide monohydrate.

Single crystals of the title compound, C(16)H(14)N(2)O(5)·H(2)O, were obtained from a condensation reaction of 1,3-benzodioxole-5-carbohydrazide and 3-methoxy-salicylaldehyde in a 95% ethanol solution. The asymmetric unit consists of a Schiff base mol-ecule, which assumes an E configuration with respect to the C=N bond, and a water mol-ecule of crystallization. The dihedral angle between the two substituted benzene rings is 12.7 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For the biological properties of hydrazones, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Okabe et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2008 ▶); Qu et al. (2008 ▶); Shan et al. (2008 ▶); Yehye et al. (2008 ▶).

Experimental

Crystal data

C16H14N2O5·H2O

M = 332.31

Orthorhombic,

a = 4.792 (2) Å

b = 12.916 (3) Å

c = 24.002 (6) Å

V = 1485.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 (2) K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.977

8595 measured reflections

1907 independent reflections

1639 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.076

S = 1.05

1907 reflections

228 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536808040117/sj2559sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040117/sj2559Isup2.hkl

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

C16H14N2O5·H2O	F(000) = 696
Mr = 332.31	Dx = 1.486 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3222 reflections
a = 4.792 (2) Å	θ = 2.4–25.6°
b = 12.916 (3) Å	µ = 0.12 mm−1
c = 24.002 (6) Å	T = 298 K
V = 1485.6 (7) Å3	Cut from needle, colorless
Z = 4	0.23 × 0.20 × 0.20 mm

Bruker SMART 1K CCD area-detector diffractometer	1907 independent reflections
Radiation source: fine-focus sealed tube	1639 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.974, Tmax = 0.977	k = −16→13
8595 measured reflections	l = −30→28

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.1335P] where P = (Fo2 + 2Fc2)/3
1907 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.13 e Å−3
4 restraints	Δρmin = −0.13 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 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
O1	0.9802 (3)	0.80320 (10)	0.83305 (6)	0.0447 (4)
H1	0.8775	0.8121	0.8061	0.067*
O2	0.3794 (4)	0.78499 (11)	0.69933 (6)	0.0563 (5)
O3	1.3470 (3)	0.79317 (11)	0.91162 (6)	0.0489 (4)
O4	−0.3191 (4)	0.81446 (12)	0.53841 (6)	0.0599 (5)
O5	−0.3991 (3)	0.98897 (11)	0.52200 (6)	0.0490 (4)
O6	0.4857 (4)	0.67908 (12)	0.79533 (6)	0.0528 (4)
N1	0.7019 (4)	0.92306 (13)	0.75678 (6)	0.0368 (4)
N2	0.5153 (4)	0.95059 (13)	0.71517 (7)	0.0374 (4)
C1	1.0510 (4)	0.98797 (15)	0.82015 (7)	0.0349 (4)
C2	1.1069 (4)	0.89400 (14)	0.84647 (8)	0.0330 (4)
C3	1.3082 (4)	0.88967 (15)	0.88912 (8)	0.0360 (4)
C4	1.4481 (5)	0.97831 (16)	0.90522 (8)	0.0415 (5)
H4	1.5789	0.9754	0.9338	0.050*
C5	1.3937 (5)	1.07197 (16)	0.87871 (8)	0.0449 (5)
H5	1.4897	1.1314	0.8893	0.054*
C6	1.1978 (5)	1.07680 (15)	0.83680 (8)	0.0418 (5)
H6	1.1624	1.1397	0.8193	0.050*
C7	0.8453 (5)	0.99888 (16)	0.77596 (8)	0.0388 (5)
H7	0.8163	1.0643	0.7608	0.047*
C8	0.3608 (5)	0.87806 (15)	0.68878 (7)	0.0371 (5)
C9	0.1638 (5)	0.91647 (14)	0.64528 (7)	0.0330 (4)
C10	0.0244 (5)	0.84061 (15)	0.61392 (8)	0.0383 (5)
H10	0.0559	0.7705	0.6200	0.046*
C11	−0.1597 (5)	0.87353 (15)	0.57404 (8)	0.0385 (5)
C12	−0.2088 (5)	0.97742 (15)	0.56457 (7)	0.0359 (4)
C13	−0.0799 (5)	1.05292 (15)	0.59480 (8)	0.0412 (5)
H13	−0.1162	1.1227	0.5885	0.049*
C14	0.1088 (5)	1.02087 (15)	0.63555 (8)	0.0386 (5)
H14	0.2004	1.0705	0.6568	0.046*
C15	−0.4686 (6)	0.88603 (18)	0.50433 (8)	0.0497 (6)
H15A	−0.6678	0.8746	0.5080	0.060*
H15B	−0.4179	0.8765	0.4655	0.060*
C16	1.5697 (5)	0.78022 (19)	0.95022 (9)	0.0522 (6)
H16A	1.5365	0.8226	0.9824	0.078*
H16B	1.7421	0.8005	0.9330	0.078*
H16C	1.5806	0.7089	0.9613	0.078*
H2	0.499 (7)	1.0186 (9)	0.7078 (10)	0.080*
H6A	0.474 (6)	0.7133 (18)	0.7649 (6)	0.080*
H6B	0.366 (5)	0.706 (2)	0.8170 (8)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0460 (9)	0.0381 (8)	0.0500 (9)	−0.0062 (7)	−0.0165 (7)	−0.0011 (7)
O2	0.0772 (12)	0.0351 (8)	0.0567 (9)	0.0061 (9)	−0.0217 (9)	0.0055 (7)
O3	0.0506 (10)	0.0414 (8)	0.0548 (8)	−0.0064 (8)	−0.0222 (8)	0.0105 (7)
O4	0.0706 (12)	0.0453 (8)	0.0638 (10)	0.0007 (9)	−0.0276 (10)	−0.0127 (8)
O5	0.0524 (10)	0.0516 (9)	0.0430 (8)	0.0055 (8)	−0.0141 (8)	−0.0009 (7)
O6	0.0684 (12)	0.0394 (8)	0.0505 (9)	0.0050 (9)	−0.0110 (9)	0.0016 (7)
N1	0.0366 (9)	0.0429 (9)	0.0308 (8)	0.0065 (8)	−0.0034 (8)	0.0020 (7)
N2	0.0394 (10)	0.0373 (9)	0.0356 (8)	0.0034 (8)	−0.0070 (8)	0.0044 (7)
C1	0.0326 (11)	0.0389 (10)	0.0333 (9)	0.0042 (9)	0.0022 (8)	−0.0020 (8)
C2	0.0319 (10)	0.0339 (9)	0.0332 (9)	−0.0007 (9)	−0.0005 (8)	−0.0039 (8)
C3	0.0357 (11)	0.0380 (10)	0.0344 (9)	−0.0002 (10)	−0.0025 (9)	0.0003 (8)
C4	0.0389 (12)	0.0462 (11)	0.0393 (10)	−0.0042 (10)	−0.0058 (10)	−0.0047 (9)
C5	0.0442 (13)	0.0380 (11)	0.0525 (12)	−0.0065 (10)	−0.0029 (11)	−0.0063 (9)
C6	0.0450 (13)	0.0335 (10)	0.0469 (11)	0.0031 (10)	0.0012 (11)	0.0001 (9)
C7	0.0418 (12)	0.0381 (10)	0.0365 (10)	0.0068 (11)	−0.0019 (9)	0.0038 (8)
C8	0.0424 (12)	0.0366 (10)	0.0323 (10)	0.0055 (10)	0.0005 (9)	0.0019 (8)
C9	0.0356 (11)	0.0333 (9)	0.0302 (9)	0.0016 (9)	0.0021 (8)	0.0020 (7)
C10	0.0446 (12)	0.0325 (10)	0.0377 (10)	0.0031 (10)	−0.0014 (10)	0.0007 (8)
C11	0.0419 (13)	0.0376 (10)	0.0360 (10)	−0.0013 (10)	−0.0009 (9)	−0.0064 (8)
C12	0.0357 (11)	0.0438 (11)	0.0283 (9)	0.0039 (9)	0.0002 (9)	0.0030 (8)
C13	0.0508 (13)	0.0314 (10)	0.0414 (10)	0.0050 (10)	−0.0056 (10)	0.0021 (9)
C14	0.0442 (12)	0.0345 (10)	0.0372 (10)	−0.0001 (9)	−0.0066 (10)	−0.0010 (8)
C15	0.0480 (14)	0.0602 (14)	0.0410 (11)	−0.0083 (13)	−0.0079 (11)	0.0006 (10)
C16	0.0456 (13)	0.0630 (14)	0.0478 (12)	−0.0021 (12)	−0.0128 (11)	0.0145 (11)

O1—C2	1.359 (2)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.377 (3)
O2—C8	1.232 (2)	C5—H5	0.9300
O3—C3	1.371 (2)	C6—H6	0.9300
O3—C16	1.423 (2)	C7—H7	0.9300
O4—C11	1.377 (2)	C8—C9	1.492 (3)
O4—C15	1.427 (3)	C9—C14	1.394 (3)
O5—C12	1.378 (2)	C9—C10	1.405 (3)
O5—C15	1.435 (3)	C10—C11	1.369 (3)
O6—H6A	0.857 (10)	C10—H10	0.9300
O6—H6B	0.848 (10)	C11—C12	1.381 (3)
N1—C7	1.282 (3)	C12—C13	1.363 (3)
N1—N2	1.387 (2)	C13—C14	1.395 (3)
N2—C8	1.352 (3)	C13—H13	0.9300
N2—H2	0.899 (10)	C14—H14	0.9300
C1—C2	1.394 (3)	C15—H15A	0.9700
C1—C6	1.404 (3)	C15—H15B	0.9700
C1—C7	1.455 (3)	C16—H16A	0.9600
C2—C3	1.408 (3)	C16—H16B	0.9600
C3—C4	1.382 (3)	C16—H16C	0.9600
C4—C5	1.392 (3)
C2—O1—H1	109.5	N2—C8—C9	116.35 (16)
C3—O3—C16	117.72 (17)	C14—C9—C10	119.66 (18)
C11—O4—C15	105.99 (16)	C14—C9—C8	123.96 (18)
C12—O5—C15	105.81 (15)	C10—C9—C8	116.36 (17)
H6A—O6—H6B	105.5 (19)	C11—C10—C9	117.68 (18)
C7—N1—N2	114.10 (16)	C11—C10—H10	121.2
C8—N2—N1	120.86 (16)	C9—C10—H10	121.2
C8—N2—H2	122.6 (19)	C10—C11—O4	128.26 (18)
N1—N2—H2	116.6 (19)	C10—C11—C12	121.75 (19)
C2—C1—C6	119.08 (18)	O4—C11—C12	109.99 (18)
C2—C1—C7	123.01 (19)	C13—C12—O5	128.10 (17)
C6—C1—C7	117.90 (18)	C13—C12—C11	122.03 (18)
O1—C2—C1	123.91 (17)	O5—C12—C11	109.86 (17)
O1—C2—C3	116.37 (16)	C12—C13—C14	117.03 (17)
C1—C2—C3	119.72 (17)	C12—C13—H13	121.5
O3—C3—C4	125.24 (18)	C14—C13—H13	121.5
O3—C3—C2	114.56 (17)	C9—C14—C13	121.83 (18)
C4—C3—C2	120.20 (18)	C9—C14—H14	119.1
C3—C4—C5	120.09 (19)	C13—C14—H14	119.1
C3—C4—H4	120.0	O4—C15—O5	108.32 (17)
C5—C4—H4	120.0	O4—C15—H15A	110.0
C6—C5—C4	120.1 (2)	O5—C15—H15A	110.0
C6—C5—H5	120.0	O4—C15—H15B	110.0
C4—C5—H5	120.0	O5—C15—H15B	110.0
C5—C6—C1	120.83 (19)	H15A—C15—H15B	108.4
C5—C6—H6	119.6	O3—C16—H16A	109.5
C1—C6—H6	119.6	O3—C16—H16B	109.5
N1—C7—C1	123.44 (18)	H16A—C16—H16B	109.5
N1—C7—H7	118.3	O3—C16—H16C	109.5
C1—C7—H7	118.3	H16A—C16—H16C	109.5
O2—C8—N2	122.73 (19)	H16B—C16—H16C	109.5
O2—C8—C9	120.92 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.04	2.743 (2)	143
O1—H1···O6	0.82	2.56	3.001 (2)	115
N2—H2···O6i	0.90 (1)	2.08 (1)	2.962 (2)	168 (3)
O6—H6A···O2	0.86 (1)	1.88 (1)	2.728 (2)	170 (3)
O6—H6B···O1ii	0.85 (1)	2.27 (2)	3.043 (2)	152 (2)
O6—H6B···O3ii	0.85 (1)	2.54 (2)	3.226 (2)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	2.04	2.743 (2)	143
O1—H1⋯O6	0.82	2.56	3.001 (2)	115
N2—H2⋯O6i	0.899 (10)	2.075 (11)	2.962 (2)	168 (3)
O6—H6A⋯O2	0.857 (10)	1.880 (12)	2.728 (2)	170 (3)
O6—H6B⋯O1ii	0.848 (10)	2.269 (16)	3.043 (2)	152 (2)
O6—H6B⋯O3ii	0.848 (10)	2.538 (19)	3.226 (2)	139 (2)

Symmetry codes: (i) ; (ii) .