2′-(4-Hydroxy­benzyl­idene)isonicotinohydrazide monohydrate

The bond lengths in the title compound, C₁₃H₁₁N₃O₂·H₂O indicate that the organic mol­ecule exists in the keto form. A network of O—H...O, O—H...N and N—H...O hydrogen bonds helps to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.108
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

2'-(4-Hydroxybenzylidene)isonicotinohydrazide monohydrate

Crystal data

C13H11N3O2·H2O	F(000) = 1088
Mr = 259.26	Dx = 1.404 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1634 reflections
a = 7.0488 (15) Å	θ = 2.8–23.0°
b = 12.150 (3) Å	µ = 0.10 mm^−1
c = 28.649 (6) Å	T = 294 K
V = 2453.6 (9) Å^3	Block, colourless
Z = 8	0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer	2512 independent reflections
Radiation source: fine-focus sealed tube	1253 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
ω scans	θmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→7
Tmin = 0.972, Tmax = 0.980	k = −15→10
12855 measured reflections	l = −35→35

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0456P)^2] where P = (Fo^2 + 2Fc^2)/3
2512 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.1008 (3)	0.31397 (16)	0.11697 (6)	0.0443 (5)
N2	0.1441 (3)	0.18591 (15)	0.28567 (6)	0.0354 (5)
H2B	0.122 (3)	0.2583 (19)	0.2882 (7)	0.043*
N3	0.1743 (2)	0.12898 (14)	0.32738 (6)	0.0361 (5)
O1	0.1971 (2)	0.03312 (12)	0.24276 (5)	0.0473 (5)
O2	0.2244 (3)	0.04210 (13)	0.54849 (5)	0.0521 (5)
H2	0.173 (4)	0.088 (2)	0.5675 (9)	0.078*
O3	0.0722 (3)	0.41313 (14)	0.31012 (6)	0.0497 (5)
H3A	0.157 (4)	0.458 (2)	0.3034 (9)	0.074*
H3B	−0.029 (4)	0.441 (2)	0.2958 (9)	0.074*
C1	0.1539 (3)	0.2086 (2)	0.11823 (8)	0.0447 (6)
H1	0.1799	0.1734	0.0901	0.054*
C2	0.1721 (3)	0.14913 (19)	0.15904 (7)	0.0391 (6)
H2A	0.2088	0.0756	0.1581	0.047*
C3	0.1356 (3)	0.19940 (18)	0.20131 (7)	0.0302 (5)
C4	0.0768 (3)	0.30829 (18)	0.20028 (7)	0.0394 (6)
H4	0.0485	0.3454	0.2278	0.047*
C5	0.0610 (3)	0.36058 (19)	0.15779 (8)	0.0447 (6)
H5	0.0197	0.4333	0.1577	0.054*
C6	0.1605 (3)	0.13260 (19)	0.24501 (7)	0.0330 (5)
C7	0.1403 (3)	0.18638 (19)	0.36383 (8)	0.0385 (6)
H7	0.0976	0.2582	0.3598	0.046*
C8	0.1643 (3)	0.14604 (17)	0.41136 (7)	0.0343 (5)
C9	0.2567 (3)	0.04828 (18)	0.42238 (8)	0.0409 (6)
H9	0.3065	0.0048	0.3986	0.049*
C10	0.2750 (3)	0.01506 (18)	0.46831 (7)	0.0421 (6)
H10	0.3378	−0.0502	0.4753	0.050*
C11	0.2003 (3)	0.07869 (18)	0.50399 (7)	0.0368 (6)
C12	0.1083 (3)	0.17606 (18)	0.49338 (8)	0.0417 (6)
H12	0.0576	0.2192	0.5171	0.050*
C13	0.0921 (3)	0.20893 (18)	0.44776 (8)	0.0413 (6)
H13	0.0312	0.2749	0.4410	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0543 (14)	0.0463 (13)	0.0322 (12)	−0.0040 (11)	0.0019 (9)	0.0038 (10)
N2	0.0533 (13)	0.0308 (10)	0.0223 (10)	−0.0005 (9)	−0.0015 (9)	0.0031 (9)
N3	0.0468 (12)	0.0377 (11)	0.0238 (11)	−0.0042 (9)	−0.0031 (9)	0.0065 (9)
O1	0.0690 (12)	0.0360 (9)	0.0368 (10)	0.0093 (9)	−0.0077 (8)	0.0001 (8)
O2	0.0781 (13)	0.0541 (11)	0.0241 (10)	0.0134 (9)	−0.0008 (9)	−0.0002 (8)
O3	0.0649 (13)	0.0379 (10)	0.0462 (11)	−0.0010 (9)	−0.0017 (10)	0.0064 (8)
C1	0.0513 (16)	0.0545 (17)	0.0281 (14)	−0.0002 (14)	0.0058 (11)	−0.0041 (12)
C2	0.0466 (15)	0.0403 (14)	0.0306 (13)	0.0021 (12)	0.0043 (11)	0.0005 (11)
C3	0.0290 (12)	0.0353 (13)	0.0262 (13)	−0.0037 (10)	−0.0021 (9)	0.0027 (10)
C4	0.0550 (15)	0.0375 (14)	0.0256 (13)	−0.0018 (12)	−0.0002 (11)	−0.0005 (10)
C5	0.0612 (17)	0.0362 (14)	0.0367 (15)	−0.0002 (13)	−0.0054 (12)	0.0055 (12)
C6	0.0330 (13)	0.0352 (13)	0.0308 (13)	−0.0002 (11)	−0.0015 (10)	0.0015 (11)
C7	0.0490 (15)	0.0356 (13)	0.0310 (14)	−0.0043 (12)	−0.0006 (11)	0.0044 (11)
C8	0.0437 (14)	0.0321 (12)	0.0269 (13)	−0.0032 (11)	−0.0017 (10)	0.0026 (10)
C9	0.0526 (15)	0.0442 (14)	0.0260 (13)	0.0053 (12)	0.0027 (12)	−0.0043 (11)
C10	0.0570 (17)	0.0379 (14)	0.0313 (14)	0.0106 (12)	−0.0013 (12)	0.0001 (11)
C11	0.0485 (15)	0.0388 (14)	0.0233 (13)	−0.0003 (12)	−0.0021 (11)	0.0005 (10)
C12	0.0558 (16)	0.0395 (14)	0.0297 (14)	0.0062 (12)	−0.0009 (11)	−0.0090 (11)
C13	0.0585 (15)	0.0314 (13)	0.0339 (14)	0.0051 (12)	−0.0068 (12)	0.0019 (11)

Geometric parameters (Å, º)

N1—C5	1.329 (3)	C3—C6	1.503 (3)
N1—C1	1.334 (3)	C4—C5	1.378 (3)
N2—C6	1.338 (3)	C4—H4	0.9300
N2—N3	1.397 (2)	C5—H5	0.9300
N2—H2B	0.90 (2)	C7—C8	1.457 (3)
N3—C7	1.279 (3)	C7—H7	0.9300
O1—C6	1.238 (2)	C8—C13	1.390 (3)
O2—C11	1.361 (2)	C8—C9	1.391 (3)
O2—H2	0.86 (3)	C9—C10	1.383 (3)
O3—H3A	0.83 (3)	C9—H9	0.9300
O3—H3B	0.89 (3)	C10—C11	1.386 (3)
C1—C2	1.381 (3)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.383 (3)
C2—C3	1.380 (3)	C12—C13	1.371 (3)
C2—H2A	0.9300	C12—H12	0.9300
C3—C4	1.387 (3)	C13—H13	0.9300
C5—N1—C1	116.4 (2)	O1—C6—C3	120.6 (2)
C6—N2—N3	119.46 (19)	N2—C6—C3	117.0 (2)
C6—N2—H2B	124.1 (13)	N3—C7—C8	123.9 (2)
N3—N2—H2B	116.3 (13)	N3—C7—H7	118.0
C7—N3—N2	113.58 (19)	C8—C7—H7	118.0
C11—O2—H2	109.3 (18)	C13—C8—C9	118.1 (2)
H3A—O3—H3B	103 (3)	C13—C8—C7	118.3 (2)
N1—C1—C2	123.4 (2)	C9—C8—C7	123.6 (2)
N1—C1—H1	118.3	C10—C9—C8	120.6 (2)
C2—C1—H1	118.3	C10—C9—H9	119.7
C3—C2—C1	119.6 (2)	C8—C9—H9	119.7
C3—C2—H2A	120.2	C9—C10—C11	120.2 (2)
C1—C2—H2A	120.2	C9—C10—H10	119.9
C2—C3—C4	117.3 (2)	C11—C10—H10	119.9
C2—C3—C6	118.0 (2)	O2—C11—C12	123.0 (2)
C4—C3—C6	124.61 (19)	O2—C11—C10	117.5 (2)
C5—C4—C3	118.9 (2)	C12—C11—C10	119.6 (2)
C5—C4—H4	120.6	C13—C12—C11	119.9 (2)
C3—C4—H4	120.6	C13—C12—H12	120.1
N1—C5—C4	124.3 (2)	C11—C12—H12	120.1
N1—C5—H5	117.8	C12—C13—C8	121.6 (2)
C4—C5—H5	117.8	C12—C13—H13	119.2
O1—C6—N2	122.4 (2)	C8—C13—H13	119.2
C6—N2—N3—C7	−174.90 (19)	C4—C3—C6—N2	−7.4 (3)
C5—N1—C1—C2	−1.4 (3)	N2—N3—C7—C8	−178.89 (18)
N1—C1—C2—C3	−0.4 (3)	N3—C7—C8—C13	−169.0 (2)
C1—C2—C3—C4	1.6 (3)	N3—C7—C8—C9	11.4 (3)
C1—C2—C3—C6	−178.89 (19)	C13—C8—C9—C10	0.2 (3)
C2—C3—C4—C5	−1.0 (3)	C7—C8—C9—C10	179.8 (2)
C6—C3—C4—C5	179.5 (2)	C8—C9—C10—C11	0.4 (3)
C1—N1—C5—C4	2.0 (3)	C9—C10—C11—O2	−179.4 (2)
C3—C4—C5—N1	−0.8 (4)	C9—C10—C11—C12	−0.5 (4)
N3—N2—C6—O1	1.9 (3)	O2—C11—C12—C13	178.8 (2)
N3—N2—C6—C3	−177.15 (17)	C10—C11—C12—C13	−0.1 (3)
C2—C3—C6—O1	−6.0 (3)	C11—C12—C13—C8	0.7 (3)
C4—C3—C6—O1	173.5 (2)	C9—C8—C13—C12	−0.7 (3)
C2—C3—C6—N2	173.09 (19)	C7—C8—C13—C12	179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O1^i	0.89 (3)	1.97 (3)	2.833 (2)	163 (2)
O3—H3A···N3^ii	0.83 (3)	2.49 (3)	3.212 (3)	146 (2)
O3—H3A···O1^ii	0.83 (3)	2.21 (3)	2.914 (2)	142 (2)
O2—H2···N1^iii	0.86 (3)	1.92 (3)	2.769 (2)	169 (3)
N2—H2B···O3	0.90 (2)	2.01 (2)	2.893 (3)	166.5 (19)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1/2, y+1/2, z; (iii) x, −y+1/2, z+1/2.