2-(1H-Indol-3-yl)acetohydrazide.

In the title compound C(10)H(11)N(3)O, the mean plane of the indole ring system (r.m.s. deviation 0.0131 Å) subtends a dihedral angle of 87.27 (5)° to the almost planar acetohydrazide substituent (r.m.s. deviation 0.0291 Å). In the crystal, bifurcated N-H⋯(O,N) and N-H⋯N hydrogen bonds involving the pyrrole N-H grouping combine to form zigzag chains along a. Additional N-H⋯O contacts from the hydrazide N-H group augmented by C-H⋯π inter-actions link the mol-ecules into chains along the a axis. The overall effect of these contacts is a three-dimensional network structure with mol-ecules stacked along the b-axis direction.

Related literature

For the use of hydrazides in the synthesis of heterocyclic compounds, see: Narayana et al. (2005a ▶,b ▶) and in the production of pharmaceuticals, see: Liu et al. (2006 ▶). For related structures, see: Butcher et al. (2007 ▶); Hou (2009 ▶); Li & Ban (2009 ▶); Sarojini et al. (2007a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

C10H11N3O

M = 189.22

Orthorhombic,

a = 12.1599 (7) Å

b = 9.6153 (4) Å

c = 16.2345 (8) Å

V = 1898.16 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.17 × 0.14 × 0.11 mm

Data collection

Bruker APEXII CCD area detector diffractometer

8600 measured reflections

2329 independent reflections

1294 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.122

S = 1.00

2329 reflections

139 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker 2005 ▶); cell refinement: APEX2 and SAINT (Bruker 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶), publCIF (Westrip 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041694/hg5253sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041694/hg5253Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041694/hg5253Isup3.cml

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

C10H11N3O	F(000) = 800
Mr = 189.22	Dx = 1.324 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1251 reflections
a = 12.1599 (7) Å	θ = 3.0–22.1°
b = 9.6153 (4) Å	µ = 0.09 mm−1
c = 16.2345 (8) Å	T = 296 K
V = 1898.16 (16) Å3	Prism, colorless
Z = 8	0.17 × 0.14 × 0.11 mm

Bruker APEXII CCD area detector diffractometer	1294 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 28.3°, θmin = 3.0°
φ and ω scans	h = −16→14
8600 measured reflections	k = −12→12
2329 independent reflections	l = −20→21

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.1536P] where P = (Fo2 + 2Fc2)/3
2329 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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	0.51122 (13)	0.27482 (16)	0.60889 (11)	0.0549 (5)
H1N	0.5591 (17)	0.321 (2)	0.5893 (12)	0.066*
C1	0.45025 (15)	0.30809 (17)	0.67668 (12)	0.0463 (5)
C2	0.46525 (18)	0.4106 (2)	0.73576 (14)	0.0615 (6)
H2	0.5251	0.4707	0.7335	0.074*
C3	0.3892 (2)	0.4202 (2)	0.79725 (14)	0.0683 (6)
H3	0.3980	0.4878	0.8377	0.082*
C4	0.29916 (19)	0.3318 (2)	0.80094 (13)	0.0664 (6)
H4	0.2479	0.3428	0.8430	0.080*
C5	0.28434 (16)	0.22822 (19)	0.74347 (12)	0.0542 (5)
H5	0.2242	0.1687	0.7466	0.065*
C6	0.36154 (14)	0.21440 (16)	0.68030 (11)	0.0418 (4)
C7	0.37296 (14)	0.12255 (16)	0.61199 (11)	0.0437 (4)
C8	0.46342 (15)	0.16439 (18)	0.57039 (12)	0.0512 (5)
H8	0.4894	0.1235	0.5222	0.061*
C9	0.29943 (16)	0.00197 (17)	0.59225 (12)	0.0526 (5)
H9A	0.2600	−0.0243	0.6418	0.063*
H9B	0.3448	−0.0764	0.5762	0.063*
C10	0.21718 (14)	0.02925 (16)	0.52500 (11)	0.0404 (4)
O10	0.18296 (11)	0.14649 (11)	0.50855 (8)	0.0575 (4)
N2	0.18364 (13)	−0.08386 (15)	0.48613 (10)	0.0505 (4)
H2N	0.2143 (16)	−0.165 (2)	0.4996 (11)	0.061*
N3	0.09921 (17)	−0.07433 (16)	0.42677 (12)	0.0631 (5)
H3N1	0.1226 (17)	−0.128 (2)	0.3824 (13)	0.076*
H3N2	0.0381 (19)	−0.125 (2)	0.4406 (14)	0.076*

	U11	U22	U33	U12	U13	U23
N1	0.0422 (9)	0.0513 (10)	0.0711 (12)	−0.0088 (7)	0.0042 (9)	0.0060 (9)
C1	0.0431 (10)	0.0411 (9)	0.0548 (11)	−0.0031 (7)	−0.0091 (9)	0.0057 (9)
C2	0.0620 (14)	0.0526 (11)	0.0699 (15)	−0.0112 (10)	−0.0161 (12)	−0.0005 (10)
C3	0.0867 (17)	0.0570 (13)	0.0612 (14)	0.0031 (12)	−0.0161 (13)	−0.0101 (11)
C4	0.0741 (15)	0.0708 (14)	0.0542 (13)	0.0138 (12)	0.0036 (11)	0.0026 (11)
C5	0.0498 (11)	0.0527 (11)	0.0600 (12)	−0.0022 (9)	0.0011 (10)	0.0136 (10)
C6	0.0415 (9)	0.0341 (8)	0.0497 (10)	0.0006 (7)	−0.0065 (8)	0.0085 (8)
C7	0.0442 (10)	0.0335 (8)	0.0534 (11)	0.0010 (7)	−0.0056 (9)	0.0087 (8)
C8	0.0537 (11)	0.0422 (10)	0.0577 (12)	0.0064 (8)	0.0021 (10)	0.0009 (9)
C9	0.0625 (12)	0.0328 (9)	0.0624 (12)	−0.0039 (8)	−0.0095 (10)	0.0070 (8)
C10	0.0444 (10)	0.0282 (8)	0.0485 (10)	−0.0012 (7)	0.0029 (8)	0.0015 (7)
O10	0.0671 (9)	0.0300 (6)	0.0752 (9)	0.0049 (6)	−0.0198 (7)	−0.0020 (6)
N2	0.0627 (10)	0.0292 (8)	0.0594 (10)	0.0020 (7)	−0.0114 (9)	−0.0020 (7)
N3	0.0782 (13)	0.0455 (10)	0.0656 (12)	−0.0004 (8)	−0.0177 (11)	−0.0082 (8)

N1—C8	1.362 (2)	C6—C7	1.425 (2)
N1—C1	1.365 (3)	C7—C8	1.352 (2)
N1—H1N	0.80 (2)	C7—C9	1.499 (2)
C1—C2	1.387 (3)	C8—H8	0.9300
C1—C6	1.407 (2)	C9—C10	1.504 (2)
C2—C3	1.364 (3)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.388 (3)	C10—O10	1.2310 (18)
C3—H3	0.9300	C10—N2	1.322 (2)
C4—C5	1.377 (3)	N2—N3	1.411 (2)
C4—H4	0.9300	N2—H2N	0.89 (2)
C5—C6	1.397 (2)	N3—H3N1	0.93 (2)
C5—H5	0.9300	N3—H3N2	0.92 (2)
C8—N1—C1	108.72 (15)	C8—C7—C6	106.48 (15)
C8—N1—H1N	124.2 (15)	C8—C7—C9	127.50 (18)
C1—N1—H1N	125.9 (15)	C6—C7—C9	126.01 (16)
N1—C1—C2	130.74 (18)	C7—C8—N1	110.48 (17)
N1—C1—C6	107.46 (16)	C7—C8—H8	124.8
C2—C1—C6	121.79 (18)	N1—C8—H8	124.8
C3—C2—C1	117.75 (19)	C7—C9—C10	114.65 (14)
C3—C2—H2	121.1	C7—C9—H9A	108.6
C1—C2—H2	121.1	C10—C9—H9A	108.6
C2—C3—C4	121.66 (19)	C7—C9—H9B	108.6
C2—C3—H3	119.2	C10—C9—H9B	108.6
C4—C3—H3	119.2	H9A—C9—H9B	107.6
C5—C4—C3	121.2 (2)	O10—C10—N2	123.07 (16)
C5—C4—H4	119.4	O10—C10—C9	122.82 (15)
C3—C4—H4	119.4	N2—C10—C9	114.10 (14)
C4—C5—C6	118.58 (18)	C10—N2—N3	119.81 (15)
C4—C5—H5	120.7	C10—N2—H2N	118.4 (12)
C6—C5—H5	120.7	N3—N2—H2N	121.8 (12)
C5—C6—C1	119.03 (17)	N2—N3—H3N1	105.6 (13)
C5—C6—C7	134.12 (16)	N2—N3—H3N2	112.8 (15)
C1—C6—C7	106.84 (16)	H3N1—N3—H3N2	97.9 (18)
C8—N1—C1—C2	179.29 (19)	C5—C6—C7—C8	177.68 (18)
C8—N1—C1—C6	0.1 (2)	C1—C6—C7—C8	−1.15 (18)
N1—C1—C2—C3	179.47 (19)	C5—C6—C7—C9	−3.4 (3)
C6—C1—C2—C3	−1.5 (3)	C1—C6—C7—C9	177.72 (16)
C1—C2—C3—C4	−0.5 (3)	C6—C7—C8—N1	1.3 (2)
C2—C3—C4—C5	1.6 (3)	C9—C7—C8—N1	−177.58 (16)
C3—C4—C5—C6	−0.7 (3)	C1—N1—C8—C7	−0.9 (2)
C4—C5—C6—C1	−1.2 (2)	C8—C7—C9—C10	−79.8 (2)
C4—C5—C6—C7	−179.92 (18)	C6—C7—C9—C10	101.5 (2)
N1—C1—C6—C5	−178.42 (15)	C7—C9—C10—O10	−26.0 (3)
C2—C1—C6—C5	2.3 (3)	C7—C9—C10—N2	155.06 (17)
N1—C1—C6—C7	0.62 (18)	O10—C10—N2—N3	−4.6 (3)
C2—C1—C6—C7	−178.61 (16)	C9—C10—N2—N3	174.30 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O10i	0.80 (2)	2.21 (2)	2.927 (2)	149.4 (19)
N1—H1N···N3i	0.80 (2)	2.50 (2)	3.126 (2)	136.6 (19)
N2—H2N···O10ii	0.89 (2)	2.20 (2)	3.0799 (19)	166.3 (17)
C9—H9A···Cg2iii	0.97	2.73	3.644 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O10i	0.80 (2)	2.21 (2)	2.927 (2)	149.4 (19)
N1—H1N⋯N3i	0.80 (2)	2.50 (2)	3.126 (2)	136.6 (19)
N2—H2N⋯O10ii	0.89 (2)	2.20 (2)	3.0799 (19)	166.3 (17)
C9—H9A⋯Cg2iii	0.97	2.73	3.644 (2)	157

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