(E)-4-Meth-oxy-N'-[(pyridin-4-yl)methyl-idene]benzohydrazide monohydrate.

In the title compound, C(14)H(13)N(3)O(2)·H(2)O, the azomethine double bond adopts an E conformation and the N-N=C-C torsion angle is 178.37 (19)°. The dihedral angle between the benzene and pyridine rings is 5.58 (12)° and the C atom of the meth-oxy group is roughly coplanar with its attached ring [deviation = 0.157 (3) Å]. In the crystal, the components are linked by O-H⋯O, O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds, forming (001) sheets. The water O atom accepts one N-H⋯O and two C-H⋯O inter-actions from the adjacent organic mol-ecule.

Related literature

For the biological activity of benzohydraazides, see: Bayrak et al. (2009 ▶). For the crystal structures of related benzohydrazides, see: Taha et al. (2012) ▶; Fun et al. (2011 ▶); Lu et al. (2009 ▶); Zhang (2009a ▶,b ▶).

Experimental

Crystal data

C14H13N3O2·H2O

M = 273.29

Monoclinic,

a = 6.6878 (5) Å

b = 7.0420 (5) Å

c = 29.249 (2) Å

β = 94.233 (2)°

V = 1373.74 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.20 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.981, T max = 0.991

7767 measured reflections

2560 independent reflections

1548 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.146

S = 1.03

2560 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034988/hb6930sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034988/hb6930Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034988/hb6930Isup3.cml

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

C14H13N3O2·H2O	F(000) = 576
Mr = 273.29	Dx = 1.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6878 (5) Å	Cell parameters from 1112 reflections
b = 7.0420 (5) Å	θ = 2.8–22.8°
c = 29.249 (2) Å	µ = 0.10 mm−1
β = 94.233 (2)°	T = 273 K
V = 1373.74 (17) Å3	Block, colourless
Z = 4	0.20 × 0.17 × 0.10 mm

Bruker SMART APEX CCD diffractometer	2560 independent reflections
Radiation source: fine-focus sealed tube	1548 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scan	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.981, Tmax = 0.991	k = −7→8
7767 measured reflections	l = −35→35

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3
2560 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.20 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	0.0974 (2)	0.3345 (3)	0.05572 (5)	0.0607 (6)
O2	0.6325 (2)	0.1818 (3)	−0.10876 (5)	0.0590 (5)
N1	0.3945 (3)	0.3260 (3)	0.09758 (6)	0.0446 (5)
H1A	0.5220	0.3083	0.0985	0.053*
N2	0.3018 (3)	0.3646 (3)	0.13646 (6)	0.0436 (5)
N3	0.1587 (4)	0.5223 (4)	0.29858 (7)	0.0662 (7)
C1	0.5874 (3)	0.2320 (3)	0.01504 (7)	0.0413 (6)
H1B	0.6640	0.2206	0.0428	0.050*
C2	0.6754 (3)	0.1988 (3)	−0.02547 (7)	0.0424 (6)
H2A	0.8102	0.1659	−0.0250	0.051*
C3	0.5623 (3)	0.2146 (3)	−0.06665 (7)	0.0424 (6)
C4	0.3619 (3)	0.2658 (4)	−0.06705 (8)	0.0513 (7)
H4A	0.2858	0.2773	−0.0948	0.062*
C5	0.2756 (3)	0.2993 (3)	−0.02691 (8)	0.0462 (6)
H5A	0.1412	0.3340	−0.0277	0.055*
C6	0.3867 (3)	0.2821 (3)	0.01516 (7)	0.0380 (5)
C7	0.2800 (3)	0.3160 (3)	0.05702 (7)	0.0411 (6)
C8	0.4126 (4)	0.3827 (4)	0.17334 (7)	0.0469 (6)
H8A	0.5506	0.3663	0.1732	0.056*
C9	0.3230 (3)	0.4292 (3)	0.21603 (7)	0.0429 (6)
C10	0.4319 (4)	0.4088 (4)	0.25789 (8)	0.0544 (7)
H10A	0.5630	0.3639	0.2592	0.065*
C11	0.3438 (5)	0.4556 (4)	0.29754 (9)	0.0650 (8)
H11A	0.4189	0.4395	0.3253	0.078*
C12	0.0554 (4)	0.5413 (4)	0.25821 (9)	0.0580 (7)
H12A	−0.0747	0.5880	0.2580	0.070*
C13	0.1279 (4)	0.4965 (4)	0.21676 (8)	0.0499 (6)
H13A	0.0476	0.5110	0.1896	0.060*
C14	0.8422 (4)	0.1550 (5)	−0.11117 (9)	0.0640 (8)
H14A	0.8706	0.1333	−0.1424	0.096*
H14B	0.8852	0.0473	−0.0929	0.096*
H14C	0.9124	0.2663	−0.0998	0.096*
O1W	0.8218 (2)	0.2877 (3)	0.12291 (5)	0.0657 (6)
H1	0.9224	0.2994	0.1078	0.098*
H2	0.8700	0.2103	0.1461	0.098*

	U11	U22	U33	U12	U13	U23
O1	0.0361 (10)	0.1027 (16)	0.0440 (10)	0.0027 (10)	0.0085 (7)	0.0049 (9)
O2	0.0496 (10)	0.0914 (15)	0.0373 (9)	−0.0042 (10)	0.0115 (8)	−0.0133 (9)
N1	0.0347 (10)	0.0645 (15)	0.0357 (11)	0.0026 (10)	0.0104 (8)	0.0015 (9)
N2	0.0415 (11)	0.0552 (13)	0.0352 (11)	0.0018 (10)	0.0111 (9)	0.0016 (9)
N3	0.0749 (17)	0.0805 (18)	0.0450 (14)	−0.0011 (14)	0.0167 (12)	−0.0098 (12)
C1	0.0384 (13)	0.0493 (15)	0.0358 (12)	0.0007 (11)	0.0012 (10)	0.0032 (10)
C2	0.0360 (13)	0.0508 (16)	0.0410 (13)	0.0012 (11)	0.0057 (10)	−0.0028 (11)
C3	0.0419 (13)	0.0485 (15)	0.0378 (13)	−0.0085 (11)	0.0102 (10)	−0.0054 (11)
C4	0.0428 (14)	0.075 (2)	0.0359 (14)	−0.0049 (13)	−0.0009 (10)	−0.0017 (12)
C5	0.0340 (13)	0.0624 (18)	0.0424 (14)	−0.0034 (12)	0.0034 (10)	0.0007 (12)
C6	0.0378 (12)	0.0403 (14)	0.0366 (12)	−0.0053 (11)	0.0068 (9)	0.0025 (10)
C7	0.0370 (13)	0.0488 (16)	0.0379 (13)	−0.0027 (11)	0.0057 (10)	0.0049 (11)
C8	0.0394 (13)	0.0605 (17)	0.0416 (14)	0.0046 (12)	0.0084 (11)	0.0005 (12)
C9	0.0454 (14)	0.0469 (16)	0.0370 (13)	−0.0016 (12)	0.0074 (10)	0.0001 (11)
C10	0.0537 (15)	0.0636 (19)	0.0456 (15)	0.0042 (14)	0.0016 (11)	−0.0006 (13)
C11	0.081 (2)	0.077 (2)	0.0368 (15)	0.0004 (17)	0.0010 (13)	−0.0006 (13)
C12	0.0553 (16)	0.0642 (19)	0.0560 (17)	−0.0004 (14)	0.0137 (13)	−0.0108 (14)
C13	0.0504 (15)	0.0574 (17)	0.0423 (14)	0.0025 (13)	0.0059 (11)	−0.0048 (12)
C14	0.0565 (17)	0.087 (2)	0.0516 (16)	0.0062 (16)	0.0226 (13)	−0.0059 (14)
O1W	0.0371 (9)	0.1143 (17)	0.0465 (10)	0.0079 (10)	0.0095 (7)	0.0166 (10)

O1—C7	1.226 (2)	C5—H5A	0.9300
O2—C3	1.370 (3)	C6—C7	1.481 (3)
O2—C14	1.422 (3)	C8—C9	1.462 (3)
N1—N2	1.362 (2)	C8—H8A	0.9300
N1—C7	1.365 (3)	C9—C10	1.385 (3)
N1—H1A	0.8600	C9—C13	1.390 (3)
N2—C8	1.269 (3)	C10—C11	1.379 (3)
N3—C11	1.326 (3)	C10—H10A	0.9300
N3—C12	1.330 (3)	C11—H11A	0.9300
C1—C2	1.382 (3)	C12—C13	1.375 (3)
C1—C6	1.388 (3)	C12—H12A	0.9300
C1—H1B	0.9300	C13—H13A	0.9300
C2—C3	1.379 (3)	C14—H14A	0.9600
C2—H2A	0.9300	C14—H14B	0.9600
C3—C4	1.387 (3)	C14—H14C	0.9600
C4—C5	1.367 (3)	O1W—H1	0.8361
C4—H4A	0.9300	O1W—H2	0.9098
C5—C6	1.395 (3)
C3—O2—C14	118.14 (18)	N1—C7—C6	116.9 (2)
N2—N1—C7	118.33 (18)	N2—C8—C9	119.9 (2)
N2—N1—H1A	120.8	N2—C8—H8A	120.1
C7—N1—H1A	120.8	C9—C8—H8A	120.1
C8—N2—N1	117.12 (19)	C10—C9—C13	117.0 (2)
C11—N3—C12	116.1 (2)	C10—C9—C8	120.7 (2)
C2—C1—C6	121.2 (2)	C13—C9—C8	122.3 (2)
C2—C1—H1B	119.4	C11—C10—C9	119.3 (2)
C6—C1—H1B	119.4	C11—C10—H10A	120.3
C3—C2—C1	119.6 (2)	C9—C10—H10A	120.3
C3—C2—H2A	120.2	N3—C11—C10	124.1 (3)
C1—C2—H2A	120.2	N3—C11—H11A	117.9
O2—C3—C2	124.7 (2)	C10—C11—H11A	117.9
O2—C3—C4	115.6 (2)	N3—C12—C13	124.5 (3)
C2—C3—C4	119.7 (2)	N3—C12—H12A	117.8
C5—C4—C3	120.5 (2)	C13—C12—H12A	117.8
C5—C4—H4A	119.8	C12—C13—C9	119.0 (2)
C3—C4—H4A	119.8	C12—C13—H13A	120.5
C4—C5—C6	120.8 (2)	C9—C13—H13A	120.5
C4—C5—H5A	119.6	O2—C14—H14A	109.5
C6—C5—H5A	119.6	O2—C14—H14B	109.5
C1—C6—C5	118.2 (2)	H14A—C14—H14B	109.5
C1—C6—C7	124.6 (2)	O2—C14—H14C	109.5
C5—C6—C7	117.2 (2)	H14A—C14—H14C	109.5
O1—C7—N1	121.0 (2)	H14B—C14—H14C	109.5
O1—C7—C6	122.1 (2)	H1—O1W—H2	101.5
C7—N1—N2—C8	−176.5 (2)	C1—C6—C7—O1	−169.8 (2)
C6—C1—C2—C3	−0.3 (3)	C5—C6—C7—O1	9.2 (3)
C14—O2—C3—C2	−9.1 (3)	C1—C6—C7—N1	10.1 (3)
C14—O2—C3—C4	171.4 (2)	C5—C6—C7—N1	−170.9 (2)
C1—C2—C3—O2	−178.8 (2)	N1—N2—C8—C9	178.37 (19)
C1—C2—C3—C4	0.7 (4)	N2—C8—C9—C10	165.7 (2)
O2—C3—C4—C5	179.1 (2)	N2—C8—C9—C13	−14.8 (4)
C2—C3—C4—C5	−0.4 (4)	C13—C9—C10—C11	−0.2 (4)
C3—C4—C5—C6	−0.3 (4)	C8—C9—C10—C11	179.4 (2)
C2—C1—C6—C5	−0.4 (3)	C12—N3—C11—C10	0.8 (4)
C2—C1—C6—C7	178.6 (2)	C9—C10—C11—N3	−0.7 (4)
C4—C5—C6—C1	0.7 (4)	C11—N3—C12—C13	0.1 (4)
C4—C5—C6—C7	−178.4 (2)	N3—C12—C13—C9	−1.0 (4)
N2—N1—C7—O1	−2.6 (3)	C10—C9—C13—C12	1.0 (4)
N2—N1—C7—C6	177.42 (18)	C8—C9—C13—C12	−178.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···O1i	0.84	2.00	2.811 (2)	162
O1W—H2···N3ii	0.91	2.11	2.956 (3)	154
N1—H1A···O1W	0.86	2.08	2.911 (2)	161
C1—H1B···O1W	0.93	2.54	3.440 (3)	162
C8—H8A···O1W	0.93	2.48	3.272 (3)	143
C11—H11A···O2iii	0.93	2.47	3.375 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯O1i	0.84	2.00	2.811 (2)	162
O1W—H2⋯N3ii	0.91	2.11	2.956 (3)	154
N1—H1A⋯O1W	0.86	2.08	2.911 (2)	161
C1—H1B⋯O1W	0.93	2.54	3.440 (3)	162
C8—H8A⋯O1W	0.93	2.48	3.272 (3)	143
C11—H11A⋯O2iii	0.93	2.47	3.375 (3)	165

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