N'-[(E)-3-Indol-3-ylmethyl-ene]isonicotino-hydrazide monohydrate.

Crystals of the title compound, C(15)H(12)N(4)O·H(2)O, were obtained from a condensation reaction of isonicotinylhydrazine and 3-indolylformaldehyde. The mol-ecule assumes an E configuration, with the isonicotinoylhydrazine and indole units located on the opposite sites of the C=N double bond. In the mol-ecular structure the pyridine ring is twisted with respect to the indole ring system, forming a dihedral angle of 44.72 (7)°. Extensive classical N-H⋯N, N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonding and weak C-H⋯O inter-actions are present in the crystal structure.

Related literature

For the applications of hydrazone derivatives in biology, see: Okabe et al. (1993 ▶). For general background to this work, see: Shan et al. (2003 ▶); Qiang et al. (2007 ▶). For the corresponding (E)-3-indolylformaldehyde isonicotinoylhydrazone methanol solvate, see: Tai et al. (2003 ▶), and (E)-3-indolylformaldehyde isonicotinoylhydrazone ethanol solvate, see: Jing et al. (2006 ▶).

Experimental

Crystal data

C15H12N4O·H2O

M = 282.30

Monoclinic,

a = 7.1984 (11) Å

b = 25.327 (4) Å

c = 7.9811 (16) Å

β = 104.062 (12)°

V = 1411.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.40 × 0.32 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

9235 measured reflections

2504 independent reflections

1575 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.161

S = 1.07

2504 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027329/xu2554sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027329/xu2554Isup2.hkl

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

C15H12N4O·H2O	F(000) = 592
Mr = 282.30	Dx = 1.328 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3236 reflections
a = 7.1984 (11) Å	θ = 2.8–25.0°
b = 25.327 (4) Å	µ = 0.09 mm−1
c = 7.9811 (16) Å	T = 294 K
β = 104.062 (12)°	Prism, colorless
V = 1411.5 (4) Å3	0.40 × 0.32 × 0.28 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	1575 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 25.2°, θmin = 2.8°
Detector resolution: 10.0 pixels mm-1	h = −8→8
ω scans	k = −30→28
9235 measured reflections	l = −9→9
2504 independent reflections

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)] = 0.055	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0753P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2504 reflections	Δρmax = 0.18 e Å−3
191 parameters	Δρmin = −0.20 e Å−3
0 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: 0.022 (4)

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	0.0721 (3)	0.27145 (8)	0.4661 (3)	0.0532 (6)
H1N	0.0189	0.2388	0.4518	0.080*
N2	0.2051 (3)	0.44265 (8)	0.6709 (3)	0.0557 (6)
N3	0.1479 (3)	0.48641 (8)	0.7552 (3)	0.0567 (6)
H3N	0.0249	0.4904	0.7553	0.085*
N4	0.0958 (3)	0.66448 (8)	1.0414 (3)	0.0585 (6)
O1	0.4458 (3)	0.52331 (7)	0.8055 (3)	0.0778 (7)
O1W	0.2725 (3)	0.51295 (8)	0.3543 (3)	0.0717 (6)
H1A	0.3680	0.5059	0.3000	0.108*
H2A	0.2989	0.4927	0.4490	0.108*
C1	0.0052 (4)	0.31058 (10)	0.5519 (3)	0.0524 (7)
H1	−0.1042	0.3081	0.5940	0.063*
C2	0.1222 (4)	0.35481 (10)	0.5685 (3)	0.0485 (7)
C3	0.4346 (4)	0.36807 (10)	0.4582 (3)	0.0520 (7)
H3	0.4625	0.4023	0.4989	0.062*
C4	0.5486 (4)	0.34271 (11)	0.3671 (4)	0.0603 (8)
H4	0.6518	0.3606	0.3429	0.072*
C5	0.5118 (4)	0.29032 (12)	0.3099 (4)	0.0630 (8)
H5	0.5931	0.2741	0.2511	0.076*
C6	0.3582 (4)	0.26257 (10)	0.3389 (3)	0.0546 (7)
H6	0.3348	0.2278	0.3019	0.066*
C7	0.2390 (4)	0.28874 (9)	0.4262 (3)	0.0469 (6)
C8	0.2756 (3)	0.34103 (9)	0.4881 (3)	0.0444 (6)
C9	0.0874 (4)	0.40330 (10)	0.6509 (3)	0.0511 (7)
H9	−0.0232	0.4063	0.6909	0.061*
C10	0.2762 (4)	0.52496 (10)	0.8150 (4)	0.0539 (7)
C11	0.2053 (4)	0.57134 (9)	0.8990 (3)	0.0483 (7)
C12	0.0156 (4)	0.58804 (10)	0.8584 (3)	0.0587 (8)
H12	−0.0785	0.5685	0.7835	0.070*
C13	−0.0314 (4)	0.63452 (10)	0.9316 (4)	0.0611 (8)
H13	−0.1585	0.6454	0.9026	0.073*
C14	0.2765 (4)	0.64680 (11)	1.0837 (4)	0.0629 (8)
H14	0.3666	0.6662	1.1632	0.076*
C15	0.3374 (4)	0.60145 (10)	1.0164 (4)	0.0590 (8)
H15	0.4652	0.5913	1.0493	0.071*

	U11	U22	U33	U12	U13	U23
N1	0.0506 (13)	0.0365 (12)	0.0698 (15)	−0.0060 (10)	0.0094 (11)	−0.0002 (11)
N2	0.0574 (14)	0.0399 (13)	0.0711 (15)	0.0061 (11)	0.0184 (12)	−0.0088 (11)
N3	0.0554 (13)	0.0399 (13)	0.0771 (16)	0.0050 (11)	0.0207 (12)	−0.0113 (11)
N4	0.0716 (16)	0.0416 (13)	0.0618 (14)	0.0087 (12)	0.0153 (12)	−0.0015 (11)
O1	0.0638 (14)	0.0592 (13)	0.1204 (18)	−0.0004 (11)	0.0418 (13)	−0.0204 (12)
O1W	0.0577 (12)	0.0756 (14)	0.0845 (14)	0.0109 (10)	0.0221 (11)	−0.0006 (11)
C1	0.0469 (15)	0.0442 (15)	0.0663 (17)	0.0017 (13)	0.0139 (13)	0.0062 (13)
C2	0.0488 (15)	0.0374 (14)	0.0575 (16)	0.0058 (12)	0.0093 (13)	0.0040 (12)
C3	0.0542 (16)	0.0382 (14)	0.0616 (17)	−0.0011 (13)	0.0099 (14)	0.0032 (12)
C4	0.0524 (16)	0.0555 (18)	0.0711 (19)	0.0016 (14)	0.0111 (15)	0.0059 (15)
C5	0.0606 (18)	0.0628 (18)	0.0662 (19)	0.0130 (16)	0.0165 (15)	−0.0018 (15)
C6	0.0597 (17)	0.0408 (15)	0.0580 (17)	0.0048 (13)	0.0039 (14)	−0.0042 (12)
C7	0.0464 (15)	0.0369 (14)	0.0524 (15)	0.0020 (12)	0.0021 (12)	−0.0006 (12)
C8	0.0454 (14)	0.0339 (14)	0.0491 (14)	0.0025 (12)	0.0021 (12)	0.0007 (11)
C9	0.0558 (16)	0.0411 (15)	0.0587 (16)	0.0054 (13)	0.0185 (13)	0.0041 (12)
C10	0.0569 (18)	0.0396 (15)	0.0677 (18)	0.0069 (13)	0.0203 (14)	0.0001 (13)
C11	0.0552 (16)	0.0371 (14)	0.0564 (16)	0.0041 (12)	0.0206 (13)	0.0036 (12)
C12	0.0615 (18)	0.0461 (15)	0.0633 (17)	0.0100 (14)	0.0048 (14)	−0.0080 (13)
C13	0.0632 (18)	0.0543 (17)	0.0625 (18)	0.0154 (15)	0.0088 (15)	−0.0032 (14)
C14	0.0634 (19)	0.0478 (17)	0.076 (2)	−0.0035 (15)	0.0131 (16)	−0.0070 (14)
C15	0.0500 (16)	0.0466 (16)	0.081 (2)	0.0017 (13)	0.0165 (15)	−0.0072 (14)

N1—C1	1.358 (3)	C3—H3	0.9300
N1—C7	1.387 (3)	C4—C5	1.407 (4)
N1—H1N	0.9057	C4—H4	0.9300
N2—C9	1.293 (3)	C5—C6	1.376 (4)
N2—N3	1.409 (3)	C5—H5	0.9300
N3—C10	1.349 (3)	C6—C7	1.397 (3)
N3—H3N	0.8916	C6—H6	0.9300
N4—C13	1.338 (3)	C7—C8	1.416 (3)
N4—C14	1.339 (3)	C9—H9	0.9300
O1—C10	1.242 (3)	C10—C11	1.502 (3)
O1W—H1A	0.9147	C11—C15	1.389 (3)
O1W—H2A	0.8945	C11—C12	1.391 (4)
C1—C2	1.388 (3)	C12—C13	1.392 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C9	1.444 (3)	C13—H13	0.9300
C2—C8	1.449 (3)	C14—C15	1.384 (4)
C3—C4	1.380 (4)	C14—H14	0.9300
C3—C8	1.403 (3)	C15—H15	0.9300
C1—N1—C7	108.6 (2)	N1—C7—C6	129.5 (2)
C1—N1—H1N	122.6	N1—C7—C8	108.3 (2)
C7—N1—H1N	128.5	C6—C7—C8	122.2 (2)
C9—N2—N3	114.0 (2)	C3—C8—C7	119.2 (2)
C10—N3—N2	118.9 (2)	C3—C8—C2	134.4 (2)
C10—N3—H3N	120.8	C7—C8—C2	106.4 (2)
N2—N3—H3N	119.7	N2—C9—C2	122.1 (2)
C13—N4—C14	116.3 (2)	N2—C9—H9	119.0
H1A—O1W—H2A	105.0	C2—C9—H9	119.0
N1—C1—C2	110.9 (2)	O1—C10—N3	123.6 (2)
N1—C1—H1	124.6	O1—C10—C11	119.9 (2)
C2—C1—H1	124.6	N3—C10—C11	116.5 (2)
C1—C2—C9	124.2 (2)	C15—C11—C12	117.6 (2)
C1—C2—C8	105.9 (2)	C15—C11—C10	118.6 (2)
C9—C2—C8	130.0 (2)	C12—C11—C10	123.7 (2)
C4—C3—C8	118.4 (2)	C11—C12—C13	119.0 (3)
C4—C3—H3	120.8	C11—C12—H12	120.5
C8—C3—H3	120.8	C13—C12—H12	120.5
C3—C4—C5	121.4 (3)	N4—C13—C12	123.9 (3)
C3—C4—H4	119.3	N4—C13—H13	118.1
C5—C4—H4	119.3	C12—C13—H13	118.1
C6—C5—C4	121.5 (3)	N4—C14—C15	124.0 (3)
C6—C5—H5	119.3	N4—C14—H14	118.0
C4—C5—H5	119.3	C15—C14—H14	118.0
C5—C6—C7	117.2 (2)	C14—C15—C11	119.2 (3)
C5—C6—H6	121.4	C14—C15—H15	120.4
C7—C6—H6	121.4	C11—C15—H15	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4i	0.91	2.06	2.961 (3)	171
N3—H3N···O1Wii	0.89	2.11	2.939 (3)	155
O1W—H1A···O1iii	0.91	1.90	2.800 (3)	168
O1W—H2A···N2	0.89	2.40	3.223 (3)	152
C12—H12···O1Wii	0.93	2.58	3.466 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N4i	0.91	2.06	2.961 (3)	171
N3—H3N⋯O1Wii	0.89	2.11	2.939 (3)	155
O1W—H1A⋯O1iii	0.91	1.90	2.800 (3)	168
O1W—H2A⋯N2	0.89	2.40	3.223 (3)	152
C12—H12⋯O1Wii	0.93	2.58	3.466 (3)	159

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