(E)-N'-(1,3-Benzodioxol-5-ylmethyl-ene)nicotinohydrazide monohydrate.

In the title compound, C(14)H(11)N(3)O(3)·H(2)O, the planar [maximum deviation 0.135 (1) Å] 1,3-benzodioxole ring system is oriented at a dihedral angle of 13.93 (7)° with respect to the pyridine ring. Extensive inter-molecular N-H⋯O, O-H⋯O, O-H⋯N and weak C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of Schiff base compounds, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C14H11N3O3·H2O

M = 287.28

Monoclinic,

a = 8.6414 (2) Å

b = 12.0874 (2) Å

c = 13.4464 (3) Å

β = 103.161 (1)°

V = 1367.61 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.26 × 0.21 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.974, T max = 0.982

19494 measured reflections

2691 independent reflections

1839 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.04

2691 reflections

199 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034503/xu2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034503/xu2599Isup2.hkl

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

C14H11N3O3·H2O	F(000) = 600
Mr = 287.28	Dx = 1.395 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2884 reflections
a = 8.6414 (2) Å	θ = 2.3–26.0°
b = 12.0874 (2) Å	µ = 0.11 mm−1
c = 13.4464 (3) Å	T = 293 K
β = 103.161 (1)°	Block, colourless
V = 1367.61 (5) Å3	0.26 × 0.21 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2691 independent reflections
Radiation source: fine-focus sealed tube	1839 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
Tmin = 0.974, Tmax = 0.982	k = −14→14
19494 measured reflections	l = −16→16

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.0682P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.010
2691 reflections	Δρmax = 0.15 e Å−3
199 parameters	Δρmin = −0.13 e Å−3
3 restraints	Extinction correction: SHELXTL (Version 5.1; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (14)

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	0.25573 (14)	0.30595 (11)	0.16863 (10)	0.0528 (4)
C7	0.46242 (17)	0.23623 (12)	0.09399 (11)	0.0469 (4)
O3	0.08396 (13)	0.45982 (9)	0.23857 (10)	0.0702 (4)
C10	−0.09502 (16)	0.32960 (12)	0.28168 (11)	0.0442 (4)
O2	0.84690 (15)	0.27321 (11)	−0.03215 (11)	0.0807 (4)
N2	0.12618 (14)	0.27993 (10)	0.20830 (10)	0.0516 (4)
H2A	0.0972	0.2122	0.2116	0.062*
C2	0.65230 (18)	0.34247 (13)	0.03595 (12)	0.0522 (4)
N3	−0.33050 (15)	0.39773 (11)	0.32710 (11)	0.0596 (4)
O1	0.73361 (16)	0.43293 (10)	0.01301 (11)	0.0842 (5)
C6	0.53331 (19)	0.14169 (13)	0.06740 (13)	0.0544 (4)
H6A	0.4908	0.0732	0.0781	0.065*
C8	0.32492 (19)	0.22390 (13)	0.13835 (12)	0.0530 (4)
H8A	0.2860	0.1532	0.1449	0.064*
C11	−0.12747 (19)	0.22473 (13)	0.31162 (13)	0.0523 (4)
H11A	−0.0606	0.1659	0.3059	0.063*
C5	0.66608 (19)	0.14538 (13)	0.02518 (13)	0.0576 (5)
H5A	0.7142	0.0814	0.0084	0.069*
C13	−0.35719 (19)	0.29587 (15)	0.35623 (13)	0.0607 (5)
H13A	−0.4466	0.2835	0.3822	0.073*
C4	0.72117 (19)	0.24715 (14)	0.00991 (13)	0.0530 (4)
C9	0.04620 (17)	0.36199 (12)	0.24153 (12)	0.0489 (4)
C1	0.52308 (19)	0.34048 (12)	0.07778 (12)	0.0520 (4)
H1B	0.4771	0.4053	0.0948	0.062*
C12	−0.26006 (19)	0.20836 (14)	0.34996 (13)	0.0606 (5)
H12A	−0.2834	0.1384	0.3714	0.073*
C14	−0.20100 (18)	0.41282 (13)	0.29066 (12)	0.0523 (4)
H14A	−0.1805	0.4837	0.2700	0.063*
C3	0.8597 (2)	0.38998 (17)	−0.02752 (16)	0.0772 (6)
H3B	0.8535	0.4197	−0.0953	0.093*
H3C	0.9612	0.4112	0.0157	0.093*
O4	−0.59280 (17)	0.54330 (10)	0.28071 (14)	0.0854 (5)
H4A	−0.5119 (16)	0.5021 (15)	0.2985 (18)	0.112 (8)*
H4B	−0.6745 (16)	0.5040 (15)	0.2633 (16)	0.102 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0450 (7)	0.0537 (8)	0.0663 (9)	−0.0044 (6)	0.0260 (7)	−0.0009 (7)
C7	0.0436 (8)	0.0483 (9)	0.0525 (9)	−0.0015 (7)	0.0187 (7)	−0.0012 (7)
O3	0.0679 (8)	0.0461 (7)	0.1111 (10)	−0.0071 (5)	0.0505 (7)	−0.0048 (6)
C10	0.0375 (8)	0.0476 (9)	0.0491 (9)	−0.0033 (6)	0.0135 (7)	−0.0031 (7)
O2	0.0748 (9)	0.0758 (9)	0.1108 (11)	−0.0141 (7)	0.0614 (8)	−0.0153 (7)
N2	0.0440 (7)	0.0454 (7)	0.0729 (9)	−0.0049 (6)	0.0294 (7)	−0.0021 (6)
C2	0.0550 (10)	0.0463 (9)	0.0600 (10)	−0.0091 (7)	0.0234 (8)	−0.0017 (7)
N3	0.0461 (8)	0.0603 (9)	0.0782 (10)	0.0029 (7)	0.0260 (7)	−0.0028 (7)
O1	0.0930 (10)	0.0566 (8)	0.1237 (11)	−0.0162 (7)	0.0675 (9)	−0.0050 (7)
C6	0.0545 (10)	0.0448 (9)	0.0698 (11)	−0.0030 (7)	0.0262 (8)	−0.0015 (8)
C8	0.0500 (9)	0.0483 (9)	0.0663 (11)	−0.0057 (7)	0.0249 (8)	−0.0030 (8)
C11	0.0499 (9)	0.0474 (9)	0.0645 (10)	0.0006 (7)	0.0235 (8)	0.0002 (8)
C5	0.0563 (10)	0.0476 (10)	0.0754 (12)	0.0023 (7)	0.0286 (9)	−0.0088 (8)
C13	0.0483 (10)	0.0688 (11)	0.0733 (12)	−0.0067 (8)	0.0312 (9)	−0.0040 (9)
C4	0.0455 (9)	0.0601 (10)	0.0597 (10)	−0.0035 (7)	0.0252 (8)	−0.0067 (8)
C9	0.0448 (9)	0.0466 (9)	0.0593 (10)	−0.0027 (7)	0.0200 (8)	0.0003 (7)
C1	0.0540 (9)	0.0454 (9)	0.0621 (10)	0.0009 (7)	0.0245 (8)	−0.0062 (7)
C12	0.0624 (11)	0.0522 (10)	0.0754 (12)	−0.0086 (8)	0.0329 (10)	0.0020 (8)
C14	0.0472 (9)	0.0467 (9)	0.0672 (10)	0.0015 (7)	0.0216 (8)	0.0019 (8)
C3	0.0742 (13)	0.0751 (13)	0.0953 (15)	−0.0113 (11)	0.0461 (11)	0.0042 (11)
O4	0.0518 (8)	0.0474 (7)	0.1622 (15)	0.0012 (6)	0.0353 (9)	0.0012 (8)

N1—C8	1.2719 (19)	O1—C3	1.423 (2)
N1—N2	1.3815 (16)	C6—C5	1.392 (2)
C7—C6	1.382 (2)	C6—H6A	0.9300
C7—C1	1.401 (2)	C8—H8A	0.9300
C7—C8	1.453 (2)	C11—C12	1.374 (2)
O3—C9	1.2299 (17)	C11—H11A	0.9300
C10—C11	1.378 (2)	C5—C4	1.351 (2)
C10—C14	1.384 (2)	C5—H5A	0.9300
C10—C9	1.4946 (19)	C13—C12	1.365 (2)
O2—C4	1.3709 (18)	C13—H13A	0.9300
O2—C3	1.416 (2)	C1—H1B	0.9300
N2—C9	1.3423 (18)	C12—H12A	0.9300
N2—H2A	0.8600	C14—H14A	0.9300
C2—C1	1.360 (2)	C3—H3B	0.9700
C2—O1	1.3723 (18)	C3—H3C	0.9700
C2—C4	1.378 (2)	O4—H4A	0.848 (9)
N3—C13	1.328 (2)	O4—H4B	0.839 (9)
N3—C14	1.3324 (19)
C8—N1—N2	115.31 (13)	C6—C5—H5A	121.9
C6—C7—C1	120.01 (14)	N3—C13—C12	123.35 (15)
C6—C7—C8	118.26 (13)	N3—C13—H13A	118.3
C1—C7—C8	121.73 (14)	C12—C13—H13A	118.3
C11—C10—C14	117.41 (13)	C5—C4—O2	127.70 (15)
C11—C10—C9	125.71 (14)	C5—C4—C2	122.33 (14)
C14—C10—C9	116.88 (13)	O2—C4—C2	109.96 (14)
C4—O2—C3	105.81 (12)	O3—C9—N2	122.63 (13)
C9—N2—N1	118.97 (12)	O3—C9—C10	120.53 (13)
C9—N2—H2A	120.5	N2—C9—C10	116.83 (13)
N1—N2—H2A	120.5	C2—C1—C7	116.86 (14)
C1—C2—O1	128.15 (14)	C2—C1—H1B	121.6
C1—C2—C4	122.21 (14)	C7—C1—H1B	121.6
O1—C2—C4	109.64 (13)	C13—C12—C11	119.27 (16)
C13—N3—C14	116.88 (14)	C13—C12—H12A	120.4
C2—O1—C3	105.75 (13)	C11—C12—H12A	120.4
C7—C6—C5	122.29 (14)	N3—C14—C10	124.09 (15)
C7—C6—H6A	118.9	N3—C14—H14A	118.0
C5—C6—H6A	118.9	C10—C14—H14A	118.0
N1—C8—C7	122.63 (15)	O2—C3—O1	108.74 (13)
N1—C8—H8A	118.7	O2—C3—H3B	109.9
C7—C8—H8A	118.7	O1—C3—H3B	109.9
C12—C11—C10	118.99 (15)	O2—C3—H3C	109.9
C12—C11—H11A	120.5	O1—C3—H3C	109.9
C10—C11—H11A	120.5	H3B—C3—H3C	108.3
C4—C5—C6	116.29 (14)	H4A—O4—H4B	109.5 (18)
C4—C5—H5A	121.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4i	0.86	2.04	2.8819 (17)	164
O4—H4A···N3	0.85 (1)	1.98 (2)	2.825 (2)	174 (2)
O4—H4B···O3ii	0.84 (1)	2.11 (2)	2.9019 (19)	158 (2)
C3—H3B···O3iii	0.97	2.57	3.495 (2)	160
C8—H8A···O4i	0.93	2.51	3.312 (2)	144
C11—H11A···O4i	0.93	2.45	3.324 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.86	2.04	2.8819 (17)	164
O4—H4A⋯N3	0.848 (9)	1.980 (17)	2.825 (2)	174 (2)
O4—H4B⋯O3ii	0.839 (9)	2.106 (15)	2.9019 (19)	158.2 (16)
C3—H3B⋯O3iii	0.97	2.57	3.495 (2)	160
C8—H8A⋯O4i	0.93	2.51	3.312 (2)	144
C11—H11A⋯O4i	0.93	2.45	3.324 (2)	156

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