(E)-N'-(2,4,5-Trimethoxy-benzyl-idene)isonicotinohydrazide dihydrate.

The asymmetric unit of the title compound, C(16)H(17)N(3)O(4)·2H(2)O, contains one Schiff base mol-ecule and two water mol-ecules. The Schiff base mol-ecule exists in an E configuration with respect to the C=N double bond and is essentially planar, the dihedral angle between the benzene and pyridine rings being 5.48 (8)°. The three meth-oxy groups are also coplanar with the benzene ring [C-O-C-C torsion angles = 3.9 (2), 178.51 (15) and 0.8 (2) Å]. In the crystal structure, the water mol-ecules link the mol-ecules into a three-dimensional network via inter-molecular N-H⋯O, O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds.

Related literature

For applications of isoniazid derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶); Kahwa et al. (1986 ▶). For the preparation of the title compound, see: Lourenco et al. (2008 ▶). For related structures, see: Naveenkumar et al. (2009 ▶, 2010a ▶,b ▶); Shi (2005 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H17N3O4·2H2O

M = 351.36

Monoclinic,

a = 6.8156 (4) Å

b = 14.5648 (10) Å

c = 8.5589 (5) Å

β = 103.421 (2)°

V = 826.42 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.50 × 0.28 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.947, T max = 0.979

10676 measured reflections

2254 independent reflections

2171 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.126

S = 1.17

2254 reflections

233 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015254/kj2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015254/kj2145Isup2.hkl

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

C16H17N3O4·2H2O	F(000) = 372
Mr = 351.36	Dx = 1.412 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6099 reflections
a = 6.8156 (4) Å	θ = 3.1–37.4°
b = 14.5648 (10) Å	µ = 0.11 mm−1
c = 8.5589 (5) Å	T = 100 K
β = 103.421 (2)°	Block, yellow
V = 826.42 (9) Å3	0.50 × 0.28 × 0.19 mm
Z = 2

Bruker APEXII DUO CCD area-detector diffractometer	2254 independent reflections
Radiation source: fine-focus sealed tube	2171 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 29.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.947, Tmax = 0.979	k = −19→19
10676 measured reflections	l = −11→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.098P)2] where P = (Fo2 + 2Fc2)/3
2254 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.57 e Å−3
1 restraint	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.7986 (2)	0.81175 (12)	1.11648 (15)	0.0180 (3)
O2	0.6823 (2)	1.23398 (11)	0.79017 (15)	0.0156 (3)
O3	0.8195 (2)	1.38828 (11)	1.30523 (16)	0.0189 (3)
O4	0.89952 (19)	1.23697 (11)	1.45332 (14)	0.0162 (3)
N1	0.6308 (2)	0.59240 (13)	0.6538 (2)	0.0172 (3)
N2	0.7323 (2)	0.91163 (13)	0.90629 (17)	0.0130 (3)
N3	0.7635 (2)	0.98623 (13)	1.00977 (19)	0.0138 (3)
C1	0.7218 (3)	0.65940 (15)	0.9179 (2)	0.0171 (4)
H1A	0.7568	0.6505	1.0285	0.020*
C2	0.6821 (3)	0.58454 (16)	0.8141 (2)	0.0206 (4)
H2A	0.6917	0.5260	0.8584	0.025*
C3	0.6190 (3)	0.67728 (16)	0.5943 (2)	0.0170 (4)
H3A	0.5837	0.6841	0.4833	0.020*
C4	0.6562 (3)	0.75638 (15)	0.6879 (2)	0.0165 (4)
H4A	0.6463	0.8141	0.6403	0.020*
C5	0.7087 (2)	0.74703 (14)	0.8545 (2)	0.0118 (4)
C6	0.7510 (2)	0.82624 (14)	0.9712 (2)	0.0126 (4)
C7	0.7415 (2)	1.06540 (15)	0.9400 (2)	0.0127 (3)
H7A	0.7100	1.0685	0.8285	0.015*
C8	0.7652 (2)	1.14993 (14)	1.0336 (2)	0.0117 (3)
C9	0.7321 (2)	1.23481 (15)	0.9547 (2)	0.0122 (4)
C10	0.7488 (3)	1.31661 (14)	1.0429 (2)	0.0131 (4)
H10A	0.7242	1.3727	0.9902	0.016*
C11	0.8021 (2)	1.31332 (14)	1.2090 (2)	0.0130 (4)
C12	0.8412 (2)	1.22870 (15)	1.2901 (2)	0.0128 (4)
C13	0.8203 (2)	1.14806 (14)	1.2032 (2)	0.0116 (3)
H13A	0.8428	1.0921	1.2566	0.014*
C14	0.6607 (3)	1.32161 (15)	0.7124 (2)	0.0168 (4)
H14A	0.6469	1.3133	0.5991	0.025*
H14B	0.7777	1.3584	0.7552	0.025*
H14C	0.5430	1.3519	0.7308	0.025*
C15	0.7866 (3)	1.47619 (16)	1.2305 (2)	0.0184 (4)
H15A	0.7906	1.5225	1.3110	0.028*
H15B	0.6571	1.4771	1.1563	0.028*
H15C	0.8900	1.4882	1.1738	0.028*
C16	0.9457 (3)	1.15432 (15)	1.5425 (2)	0.0176 (4)
H16A	1.0034	1.1687	1.6531	0.026*
H16B	1.0403	1.1191	1.4999	0.026*
H16C	0.8244	1.1193	1.5348	0.026*
H1N2	0.692 (4)	0.923 (2)	0.803 (3)	0.017 (6)*
O2W	0.6218 (2)	0.96947 (12)	0.57107 (16)	0.0189 (3)
H1W2	0.7145	0.9636	0.5228	0.028*
H2W2	0.5246	0.9958	0.5113	0.028*
O1W	0.8961 (2)	0.92446 (13)	0.39361 (16)	0.0228 (3)
H1W1	0.9693	0.8884	0.4600	0.034*
H2W1	0.8554	0.8950	0.3055	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0273 (7)	0.0138 (8)	0.0110 (6)	0.0009 (5)	0.0009 (5)	0.0001 (5)
O2	0.0256 (6)	0.0115 (7)	0.0088 (6)	−0.0002 (5)	0.0017 (4)	0.0008 (5)
O3	0.0313 (7)	0.0101 (7)	0.0128 (6)	0.0004 (6)	0.0003 (5)	−0.0028 (5)
O4	0.0261 (6)	0.0122 (7)	0.0085 (5)	0.0014 (5)	0.0004 (4)	0.0006 (5)
N1	0.0194 (6)	0.0137 (9)	0.0176 (8)	−0.0008 (6)	0.0025 (5)	−0.0044 (6)
N2	0.0178 (6)	0.0097 (8)	0.0105 (6)	−0.0013 (6)	0.0016 (5)	−0.0023 (6)
N3	0.0161 (6)	0.0103 (8)	0.0143 (6)	−0.0011 (6)	0.0020 (5)	−0.0030 (6)
C1	0.0249 (8)	0.0123 (10)	0.0136 (8)	−0.0001 (7)	0.0035 (6)	0.0005 (7)
C2	0.0328 (9)	0.0099 (10)	0.0185 (9)	−0.0008 (8)	0.0045 (7)	−0.0008 (8)
C3	0.0202 (7)	0.0144 (10)	0.0148 (8)	0.0010 (7)	0.0010 (6)	−0.0023 (7)
C4	0.0214 (8)	0.0126 (10)	0.0139 (8)	0.0016 (7)	0.0008 (6)	0.0002 (7)
C5	0.0122 (6)	0.0100 (10)	0.0128 (7)	−0.0002 (6)	0.0025 (5)	−0.0016 (7)
C6	0.0132 (7)	0.0126 (10)	0.0115 (7)	−0.0002 (6)	0.0018 (5)	−0.0008 (6)
C7	0.0137 (6)	0.0121 (9)	0.0119 (7)	−0.0008 (6)	0.0024 (5)	−0.0031 (7)
C8	0.0138 (7)	0.0094 (9)	0.0118 (8)	−0.0003 (6)	0.0025 (5)	−0.0013 (6)
C9	0.0136 (7)	0.0125 (9)	0.0100 (7)	−0.0007 (7)	0.0017 (5)	−0.0017 (7)
C10	0.0169 (7)	0.0090 (9)	0.0129 (7)	−0.0001 (7)	0.0024 (6)	−0.0007 (7)
C11	0.0153 (7)	0.0098 (10)	0.0133 (8)	−0.0003 (7)	0.0020 (6)	−0.0026 (7)
C12	0.0145 (6)	0.0136 (10)	0.0095 (7)	0.0005 (7)	0.0010 (5)	−0.0003 (7)
C13	0.0126 (6)	0.0098 (9)	0.0121 (7)	−0.0006 (6)	0.0020 (5)	0.0006 (6)
C14	0.0252 (8)	0.0124 (10)	0.0123 (7)	0.0002 (7)	0.0034 (6)	0.0018 (7)
C15	0.0255 (8)	0.0096 (9)	0.0185 (8)	0.0006 (7)	0.0016 (6)	−0.0027 (7)
C16	0.0244 (8)	0.0154 (10)	0.0129 (7)	0.0018 (7)	0.0042 (6)	0.0042 (7)
O2W	0.0265 (6)	0.0172 (8)	0.0127 (6)	0.0040 (6)	0.0039 (5)	0.0029 (6)
O1W	0.0282 (7)	0.0261 (9)	0.0118 (6)	0.0080 (6)	0.0002 (5)	−0.0026 (6)

O1—C6	1.228 (2)	C7—H7A	0.9300
O2—C9	1.3700 (19)	C8—C9	1.402 (3)
O2—C14	1.431 (2)	C8—C13	1.412 (2)
O3—C11	1.356 (2)	C9—C10	1.401 (3)
O3—C15	1.426 (3)	C10—C11	1.384 (2)
O4—C12	1.366 (2)	C10—H10A	0.9300
O4—C16	1.421 (2)	C11—C12	1.410 (3)
N1—C3	1.332 (3)	C12—C13	1.380 (3)
N1—C2	1.340 (3)	C13—H13A	0.9300
N2—C6	1.356 (3)	C14—H14A	0.9600
N2—N3	1.387 (2)	C14—H14B	0.9600
N2—H1N2	0.88 (3)	C14—H14C	0.9600
N3—C7	1.291 (3)	C15—H15A	0.9600
C1—C5	1.381 (3)	C15—H15B	0.9600
C1—C2	1.393 (3)	C15—H15C	0.9600
C1—H1A	0.9300	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.392 (3)	C16—H16C	0.9600
C3—H3A	0.9300	O2W—H1W2	0.8358
C4—C5	1.394 (2)	O2W—H2W2	0.8306
C4—H4A	0.9300	O1W—H1W1	0.8468
C5—C6	1.509 (3)	O1W—H2W1	0.8562
C7—C8	1.457 (3)
C9—O2—C14	116.38 (15)	C10—C9—C8	120.44 (15)
C11—O3—C15	117.89 (14)	C11—C10—C9	119.55 (17)
C12—O4—C16	116.76 (16)	C11—C10—H10A	120.2
C3—N1—C2	116.66 (17)	C9—C10—H10A	120.2
C6—N2—N3	118.09 (14)	O3—C11—C10	124.14 (17)
C6—N2—H1N2	124 (2)	O3—C11—C12	115.12 (15)
N3—N2—H1N2	117 (2)	C10—C11—C12	120.74 (17)
C7—N3—N2	114.86 (15)	O4—C12—C13	126.55 (18)
C5—C1—C2	119.19 (17)	O4—C12—C11	113.82 (17)
C5—C1—H1A	120.4	C13—C12—C11	119.64 (15)
C2—C1—H1A	120.4	C12—C13—C8	120.47 (17)
N1—C2—C1	123.5 (2)	C12—C13—H13A	119.8
N1—C2—H2A	118.2	C8—C13—H13A	119.8
C1—C2—H2A	118.2	O2—C14—H14A	109.5
N1—C3—C4	124.15 (17)	O2—C14—H14B	109.5
N1—C3—H3A	117.9	H14A—C14—H14B	109.5
C4—C3—H3A	117.9	O2—C14—H14C	109.5
C3—C4—C5	118.48 (18)	H14A—C14—H14C	109.5
C3—C4—H4A	120.8	H14B—C14—H14C	109.5
C5—C4—H4A	120.8	O3—C15—H15A	109.5
C1—C5—C4	118.01 (17)	O3—C15—H15B	109.5
C1—C5—C6	117.48 (15)	H15A—C15—H15B	109.5
C4—C5—C6	124.52 (18)	O3—C15—H15C	109.5
O1—C6—N2	123.39 (17)	H15A—C15—H15C	109.5
O1—C6—C5	120.23 (18)	H15B—C15—H15C	109.5
N2—C6—C5	116.38 (15)	O4—C16—H16A	109.5
N3—C7—C8	120.95 (15)	O4—C16—H16B	109.5
N3—C7—H7A	119.5	H16A—C16—H16B	109.5
C8—C7—H7A	119.5	O4—C16—H16C	109.5
C9—C8—C13	119.13 (16)	H16A—C16—H16C	109.5
C9—C8—C7	119.69 (15)	H16B—C16—H16C	109.5
C13—C8—C7	121.18 (17)	H1W2—O2W—H2W2	109.2
O2—C9—C10	122.09 (17)	H1W1—O1W—H2W1	107.4
O2—C9—C8	117.47 (16)
C6—N2—N3—C7	−179.38 (14)	C13—C8—C9—O2	178.90 (14)
C3—N1—C2—C1	0.2 (3)	C7—C8—C9—O2	−1.3 (2)
C5—C1—C2—N1	−0.1 (3)	C13—C8—C9—C10	−1.5 (2)
C2—N1—C3—C4	−0.1 (3)	C7—C8—C9—C10	178.21 (15)
N1—C3—C4—C5	−0.2 (3)	O2—C9—C10—C11	−179.21 (14)
C2—C1—C5—C4	−0.1 (3)	C8—C9—C10—C11	1.3 (2)
C2—C1—C5—C6	179.42 (16)	C15—O3—C11—C10	−1.9 (2)
C3—C4—C5—C1	0.3 (3)	C15—O3—C11—C12	178.51 (15)
C3—C4—C5—C6	−179.27 (16)	C9—C10—C11—O3	−179.05 (15)
N3—N2—C6—O1	−1.7 (2)	C9—C10—C11—C12	0.5 (2)
N3—N2—C6—C5	177.93 (14)	C16—O4—C12—C13	0.8 (2)
C1—C5—C6—O1	1.3 (2)	C16—O4—C12—C11	−178.67 (14)
C4—C5—C6—O1	−179.19 (16)	O3—C11—C12—O4	−2.9 (2)
C1—C5—C6—N2	−178.42 (15)	C10—C11—C12—O4	177.57 (14)
C4—C5—C6—N2	1.1 (2)	O3—C11—C12—C13	177.65 (15)
N2—N3—C7—C8	178.65 (14)	C10—C11—C12—C13	−1.9 (2)
N3—C7—C8—C9	−177.35 (15)	O4—C12—C13—C8	−177.80 (15)
N3—C7—C8—C13	2.4 (2)	C11—C12—C13—C8	1.6 (2)
C14—O2—C9—C10	3.9 (2)	C9—C8—C13—C12	0.1 (2)
C14—O2—C9—C8	−176.53 (14)	C7—C8—C13—C12	−179.66 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2W	0.88 (3)	2.05 (3)	2.916 (2)	171 (2)
O2W—H1W2···O1W	0.84	1.93	2.748 (2)	167
O2W—H2W2···N1i	0.83	2.10	2.887 (2)	158
O1W—H1W1···O3ii	0.85	2.18	2.8913 (19)	141
O1W—H1W1···O4ii	0.85	2.43	3.204 (2)	152
O1W—H2W1···O1iii	0.86	1.99	2.834 (2)	170
C4—H4A···O2W	0.93	2.34	3.253 (3)	169
C7—H7A···O2W	0.93	2.58	3.375 (2)	143
C14—H14A···O4iii	0.96	2.60	3.281 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2W	0.88 (3)	2.05 (3)	2.916 (2)	171 (2)
O2W—H1W2⋯O1W	0.84	1.93	2.748 (2)	167
O2W—H2W2⋯N1i	0.83	2.10	2.887 (2)	158
O1W—H1W1⋯O3ii	0.85	2.18	2.8913 (19)	141
O1W—H1W1⋯O4ii	0.85	2.43	3.204 (2)	152
O1W—H2W1⋯O1iii	0.86	1.99	2.834 (2)	170
C4—H4A⋯O2W	0.93	2.34	3.253 (3)	169
C7—H7A⋯O2W	0.93	2.58	3.375 (2)	143
C14—H14A⋯O4iii	0.96	2.60	3.281 (2)	128

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