(E)-N'-(4-Meth-oxy-benzyl-idene)pyridine-3-carbohydrazide dihydrate.

In the title compound, C14H13N3O2·2H2O, the hydrazone mol-ecule adopts an E conformation with respect to the C=N bond. The dihedral angle between the benzene and pyridine rings is 8.55 (10)°. The methyl-idene-hydrazide [-C(=O)-N-N=C-] fragment is essentially planar, with a maximum deviation of 0.0375 (13) Å. The mean planes of the benzene and pyridine rings make dihedral angles of 2.71 (14) and 11.25 (13)°, respectively, with mean plane of the methyl-idene-hydrazide fragment. In the crystal, the benzohydrazide and water mol-ecules are linked by N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds into a three-dimensional network.

Related literature

For the biological activity of benzohydrazides, see: Hai-Yun (2011 ▶); Havanur et al. (2010 ▶); Parashar et al. (2009 ▶). For details of the ability of benzohydrazone compounds to inhibit cell growth and DNA synthesis, see: Ambwani et al. (2011 ▶); Despaigne et al. (2010 ▶); Havanur et al. (2010 ▶). For background to the use of benzohydrazides as catalysts, see: Seleem et al. (2011 ▶); Singh & Raghav (2011 ▶). For related structures, see: Ahmad et al. (2010 ▶); Hu & Liu (2012 ▶); Shi & Li (2012 ▶).

Experimental

Crystal data

C14H13N3O2·2H2O

M = 291.31

Monoclinic,

a = 7.6534 (6) Å

b = 16.3503 (11) Å

c = 11.4887 (6) Å

β = 96.889 (2)°

V = 1427.26 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.970, T max = 0.980

11391 measured reflections

3449 independent reflections

2050 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.155

S = 0.93

3449 reflections

206 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017406/sj5336sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017406/sj5336Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017406/sj5336Isup3.cml

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

C14H13N3O2·2H2O	F(000) = 616
Mr = 291.31	Dx = 1.356 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2772 reflections
a = 7.6534 (6) Å	θ = 5.0–49.6°
b = 16.3503 (11) Å	µ = 0.10 mm−1
c = 11.4887 (6) Å	T = 296 K
β = 96.889 (2)°	Block, colorless
V = 1427.26 (17) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3449 independent reflections
Radiation source: fine-focus sealed tube	2050 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 28.2°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→10
Tmin = 0.970, Tmax = 0.980	k = −21→21
11391 measured reflections	l = −13→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0961P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max = 0.001
3449 reflections	Δρmax = 0.21 e Å−3
206 parameters	Δρmin = −0.17 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

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
O1W	−0.21558 (17)	0.92875 (9)	0.70457 (12)	0.0661 (4)
O1	0.21045 (18)	1.39338 (7)	0.86316 (12)	0.0652 (4)
O2W	0.4378 (2)	1.01711 (9)	1.14079 (13)	0.0670 (4)
N1	0.15479 (18)	1.00258 (8)	0.89482 (11)	0.0459 (4)
N2	0.09417 (18)	0.92297 (7)	0.87676 (11)	0.0449 (4)
H2N2	0.0061	0.9121	0.8253	0.054*
N3	0.1583 (2)	0.63790 (8)	0.97900 (12)	0.0530 (4)
O2	0.29733 (18)	0.87747 (7)	1.01980 (11)	0.0688 (5)
C1	0.3384 (3)	1.42723 (12)	0.9485 (2)	0.0717 (6)
H1A	0.3071	1.4158	1.0253	0.108*
H1B	0.3438	1.4853	0.9375	0.108*
H1C	0.4512	1.4035	0.9408	0.108*
C2	0.1867 (2)	1.31049 (10)	0.86152 (14)	0.0470 (4)
C3	0.2804 (2)	1.25610 (10)	0.93809 (15)	0.0477 (4)
H3	0.3671	1.2753	0.9952	0.057*
C4	0.2445 (2)	1.17334 (10)	0.92929 (14)	0.0460 (4)
H4	0.3080	1.1372	0.9806	0.055*
C5	0.1152 (2)	1.14332 (9)	0.84510 (13)	0.0413 (4)
C8	0.0684 (2)	1.05745 (10)	0.83445 (14)	0.0450 (4)
H8	−0.0278	1.0421	0.7818	0.054*
C9	0.1777 (2)	0.86340 (9)	0.94232 (13)	0.0422 (4)
C10	0.1187 (2)	0.77765 (9)	0.91597 (13)	0.0384 (4)
C14	0.1898 (2)	0.71787 (10)	0.99233 (13)	0.0467 (4)
H14	0.2650	0.7345	1.0577	0.056*
C13	0.0525 (2)	0.61574 (10)	0.88326 (15)	0.0520 (5)
H13	0.0303	0.5603	0.8708	0.062*
C6	0.0240 (2)	1.19971 (10)	0.76869 (14)	0.0482 (4)
H6	−0.0629	1.1809	0.7114	0.058*
C7	0.0592 (2)	1.28169 (10)	0.77585 (15)	0.0509 (4)
H7	−0.0022	1.3178	0.7234	0.061*
C12	−0.0253 (2)	0.67021 (10)	0.80237 (15)	0.0519 (5)
H12	−0.0988	0.6519	0.7373	0.062*
C11	0.0072 (2)	0.75257 (9)	0.81904 (14)	0.0456 (4)
H11	−0.0452	0.7907	0.7658	0.055*
H1O1	−0.266 (2)	0.9158 (11)	0.6408 (10)	0.068*
H2O1	−0.291 (2)	0.9418 (13)	0.7474 (13)	0.068*
H2O2	0.389 (3)	0.9826 (11)	1.0949 (17)	0.077 (7)*
H1O2	0.544 (2)	1.021 (2)	1.134 (3)	0.149 (15)*

	U11	U22	U33	U12	U13	U23
O1W	0.0546 (9)	0.0784 (9)	0.0607 (9)	−0.0029 (7)	−0.0121 (7)	−0.0218 (7)
O1	0.0764 (10)	0.0408 (7)	0.0760 (9)	−0.0070 (6)	−0.0009 (8)	0.0042 (6)
O2W	0.0648 (10)	0.0722 (9)	0.0623 (9)	−0.0155 (8)	0.0000 (8)	−0.0202 (7)
N1	0.0494 (8)	0.0396 (7)	0.0464 (8)	−0.0076 (6)	−0.0043 (7)	−0.0017 (6)
N2	0.0468 (8)	0.0403 (7)	0.0440 (8)	−0.0064 (6)	−0.0088 (6)	−0.0030 (6)
N3	0.0636 (10)	0.0439 (8)	0.0487 (8)	−0.0001 (7)	−0.0054 (7)	0.0017 (6)
O2	0.0731 (9)	0.0519 (7)	0.0702 (9)	−0.0125 (6)	−0.0370 (8)	0.0024 (6)
C1	0.0695 (14)	0.0482 (10)	0.0957 (16)	−0.0127 (9)	0.0025 (12)	−0.0117 (10)
C2	0.0523 (10)	0.0401 (9)	0.0497 (9)	−0.0011 (7)	0.0111 (8)	−0.0009 (7)
C3	0.0489 (10)	0.0472 (9)	0.0450 (9)	−0.0052 (7)	−0.0023 (8)	−0.0042 (7)
C4	0.0500 (10)	0.0418 (9)	0.0439 (9)	0.0017 (7)	−0.0030 (8)	0.0007 (7)
C5	0.0427 (9)	0.0420 (8)	0.0386 (8)	−0.0005 (7)	0.0022 (7)	−0.0033 (6)
C8	0.0447 (9)	0.0457 (9)	0.0420 (9)	−0.0029 (7)	−0.0049 (7)	−0.0037 (7)
C9	0.0428 (9)	0.0436 (9)	0.0383 (8)	−0.0055 (7)	−0.0026 (7)	−0.0010 (6)
C10	0.0380 (8)	0.0421 (8)	0.0343 (8)	−0.0016 (7)	0.0009 (7)	−0.0026 (6)
C14	0.0518 (10)	0.0479 (9)	0.0375 (9)	−0.0021 (8)	−0.0068 (8)	−0.0020 (7)
C13	0.0578 (11)	0.0413 (9)	0.0546 (10)	−0.0017 (8)	−0.0021 (9)	−0.0064 (7)
C6	0.0478 (10)	0.0500 (10)	0.0441 (9)	0.0022 (8)	−0.0062 (8)	−0.0028 (7)
C7	0.0554 (11)	0.0477 (9)	0.0480 (9)	0.0074 (8)	−0.0003 (8)	0.0046 (7)
C12	0.0555 (11)	0.0484 (9)	0.0478 (9)	−0.0034 (8)	−0.0100 (8)	−0.0096 (8)
C11	0.0486 (10)	0.0442 (9)	0.0412 (9)	0.0013 (7)	−0.0068 (8)	0.0003 (7)

O1W—H1O1	0.814 (9)	C3—H3	0.9300
O1W—H2O1	0.828 (9)	C4—C5	1.388 (2)
O1—C2	1.3672 (19)	C4—H4	0.9300
O1—C1	1.413 (2)	C5—C6	1.400 (2)
O2W—H2O2	0.830 (15)	C5—C8	1.450 (2)
O2W—H1O2	0.828 (17)	C8—H8	0.9300
N1—C8	1.270 (2)	C9—C10	1.493 (2)
N1—N2	1.3890 (17)	C10—C11	1.382 (2)
N2—C9	1.3451 (19)	C10—C14	1.381 (2)
N2—H2N2	0.8600	C14—H14	0.9300
N3—C14	1.335 (2)	C13—C12	1.370 (2)
N3—C13	1.335 (2)	C13—H13	0.9300
O2—C9	1.2199 (18)	C6—C7	1.368 (2)
C1—H1A	0.9600	C6—H6	0.9300
C1—H1B	0.9600	C7—H7	0.9300
C1—H1C	0.9600	C12—C11	1.379 (2)
C2—C7	1.383 (2)	C12—H12	0.9300
C2—C3	1.388 (2)	C11—H11	0.9300
C3—C4	1.382 (2)
H1O1—O1W—H2O1	108.4 (17)	N1—C8—H8	119.0
C2—O1—C1	118.54 (14)	C5—C8—H8	119.0
H2O2—O2W—H1O2	111 (2)	O2—C9—N2	122.46 (14)
C8—N1—N2	115.97 (13)	O2—C9—C10	120.50 (14)
C9—N2—N1	117.85 (12)	N2—C9—C10	117.04 (13)
C9—N2—H2N2	121.1	C11—C10—C14	117.41 (14)
N1—N2—H2N2	121.1	C11—C10—C9	125.79 (14)
C14—N3—C13	116.33 (13)	C14—C10—C9	116.70 (13)
O1—C1—H1A	109.5	N3—C14—C10	124.64 (14)
O1—C1—H1B	109.5	N3—C14—H14	117.7
H1A—C1—H1B	109.5	C10—C14—H14	117.7
O1—C1—H1C	109.5	N3—C13—C12	123.60 (15)
H1A—C1—H1C	109.5	N3—C13—H13	118.2
H1B—C1—H1C	109.5	C12—C13—H13	118.2
O1—C2—C7	115.38 (14)	C7—C6—C5	121.87 (14)
O1—C2—C3	124.65 (14)	C7—C6—H6	119.1
C7—C2—C3	119.97 (14)	C5—C6—H6	119.1
C4—C3—C2	119.85 (14)	C6—C7—C2	119.58 (15)
C4—C3—H3	120.1	C6—C7—H7	120.2
C2—C3—H3	120.1	C2—C7—H7	120.2
C3—C4—C5	121.08 (14)	C13—C12—C11	118.95 (14)
C3—C4—H4	119.5	C13—C12—H12	120.5
C5—C4—H4	119.5	C11—C12—H12	120.5
C4—C5—C6	117.64 (14)	C12—C11—C10	119.05 (14)
C4—C5—C8	123.31 (14)	C12—C11—H11	120.5
C6—C5—C8	119.04 (13)	C10—C11—H11	120.5
N1—C8—C5	122.07 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N2···O1W	0.86	2.08	2.9013 (17)	161
O1W—H1O1···N3i	0.81 (1)	2.08 (1)	2.8697 (18)	166 (2)
O1W—H2O1···O2Wii	0.83 (1)	1.93 (1)	2.749 (2)	171 (2)
O2W—H1O2···N1iii	0.83 (2)	2.40 (2)	3.209 (2)	166 (3)
O2W—H2O2···O2	0.83 (2)	2.01 (2)	2.8182 (17)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N2⋯O1W	0.86	2.08	2.9013 (17)	161
O1W—H1O1⋯N3i	0.81 (1)	2.08 (1)	2.8697 (18)	166 (2)
O1W—H2O1⋯O2W ii	0.83 (1)	1.93 (1)	2.749 (2)	171 (2)
O2W—H1O2⋯N1iii	0.83 (2)	2.40 (2)	3.209 (2)	166 (3)
O2W—H2O2⋯O2	0.83 (2)	2.01 (2)	2.8182 (17)	164 (2)

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