1H-Pyrrole-2-carbohydrazide.

The title compound, C(5)H(7)N(3)O, was obtained by the reaction of ethyl 1H-pyrrol-2-carboxyl-ate and hydrazide hydrate. In the crystal, mol-ecules are linked via inter-molecular N-H⋯N and N-H⋯O hydrogen bonds, forming a supra-molecular grid.

Related literature

For background to pyrrole derivatives and their biological activity, see: Joshi et al. (2008 ▶); Demirayak et al. (1999 ▶); Halazy & Magnus (1984 ▶); Bijev (2006 ▶); Sbardella et al. (2004 ▶).

Experimental

Crystal data

C5H7N3O

M = 125.14

Orthorhombic,

a = 9.9789 (16) Å

b = 8.5633 (14) Å

c = 13.657 (2) Å

V = 1167.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.31 × 0.28 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.968, T max = 0.983

5327 measured reflections

1043 independent reflections

758 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.146

S = 1.04

1043 reflections

90 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002650/fy2001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002650/fy2001Isup2.hkl

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

C5H7N3O	Dx = 1.424 Mg m−3
Mr = 125.14	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 990 reflections
a = 9.9789 (16) Å	θ = 3.0–22.4°
b = 8.5633 (14) Å	µ = 0.11 mm−1
c = 13.657 (2) Å	T = 296 K
V = 1167.0 (3) Å3	Block, colourless
Z = 8	0.31 × 0.28 × 0.16 mm
F(000) = 528

Bruker APEXII CCD diffractometer	1043 independent reflections
Radiation source: fine-focus sealed tube	758 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.968, Tmax = 0.983	k = −6→10
5327 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0957P)2] where P = (Fo2 + 2Fc2)/3
1043 reflections	(Δ/σ)max < 0.001
90 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 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	0.55417 (12)	0.04787 (18)	0.64606 (11)	0.0469 (5)
H1	0.6352	0.0752	0.6332	0.056*
N2	0.34109 (14)	0.28224 (17)	0.48978 (11)	0.0495 (5)
H2	0.2667	0.2414	0.5087	0.059*
N3	0.33807 (16)	0.3955 (2)	0.41573 (15)	0.0551 (5)
O1	0.56366 (11)	0.29286 (15)	0.50912 (10)	0.0538 (5)
C1	0.5178 (2)	−0.0654 (2)	0.71020 (14)	0.0523 (5)
H1A	0.5761	−0.1266	0.7470	0.063*
C2	0.3816 (2)	−0.0744 (2)	0.71164 (14)	0.0544 (6)
H2A	0.3304	−0.1421	0.7495	0.065*
C3	0.33310 (17)	0.0371 (2)	0.64571 (14)	0.0510 (6)
H3	0.2435	0.0573	0.6318	0.061*
C4	0.44238 (15)	0.1116 (2)	0.60516 (13)	0.0418 (5)
C5	0.45432 (16)	0.2352 (2)	0.53214 (13)	0.0423 (5)
H3A	0.394 (3)	0.359 (3)	0.3665 (19)	0.086 (8)*
H3B	0.380 (3)	0.483 (3)	0.4387 (19)	0.095 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0320 (8)	0.0562 (10)	0.0526 (10)	−0.0009 (7)	0.0010 (6)	0.0026 (8)
N2	0.0285 (8)	0.0569 (10)	0.0631 (10)	−0.0010 (6)	0.0003 (6)	0.0119 (8)
N3	0.0383 (10)	0.0595 (12)	0.0674 (12)	−0.0003 (8)	−0.0021 (8)	0.0121 (10)
O1	0.0304 (8)	0.0574 (9)	0.0737 (10)	−0.0019 (5)	0.0016 (6)	0.0054 (7)
C1	0.0483 (11)	0.0604 (12)	0.0481 (11)	0.0021 (9)	−0.0002 (8)	0.0056 (10)
C2	0.0455 (12)	0.0631 (13)	0.0545 (12)	−0.0060 (9)	0.0063 (9)	0.0041 (10)
C3	0.0357 (10)	0.0618 (12)	0.0554 (12)	−0.0037 (9)	0.0001 (8)	−0.0008 (10)
C4	0.0336 (9)	0.0469 (11)	0.0447 (10)	−0.0001 (7)	−0.0003 (7)	−0.0048 (8)
C5	0.0319 (10)	0.0452 (10)	0.0497 (11)	0.0003 (8)	0.0005 (7)	−0.0091 (9)

N1—C1	1.356 (2)	O1—C5	1.2380 (18)
N1—C4	1.362 (2)	C1—C2	1.361 (3)
N1—H1	0.8600	C1—H1A	0.9300
N2—C5	1.332 (2)	C2—C3	1.399 (3)
N2—N3	1.402 (2)	C2—H2A	0.9300
N2—H2	0.8600	C3—C4	1.380 (2)
N3—H3A	0.93 (3)	C3—H3	0.9300
N3—H3B	0.91 (3)	C4—C5	1.459 (3)
C1—N1—C4	109.41 (15)	C1—C2—C3	107.33 (17)
C1—N1—H1	125.3	C1—C2—H2A	126.3
C4—N1—H1	125.3	C3—C2—H2A	126.3
C5—N2—N3	122.74 (15)	C4—C3—C2	107.48 (16)
C5—N2—H2	118.6	C4—C3—H3	126.3
N3—N2—H2	118.6	C2—C3—H3	126.3
N2—N3—H3A	106.1 (15)	N1—C4—C3	107.30 (17)
N2—N3—H3B	108.1 (17)	N1—C4—C5	120.28 (14)
H3A—N3—H3B	104 (2)	C3—C4—C5	132.42 (15)
N1—C1—C2	108.47 (17)	O1—C5—N2	121.13 (18)
N1—C1—H1A	125.8	O1—C5—C4	122.32 (15)
C2—C1—H1A	125.8	N2—C5—C4	116.54 (15)
C4—N1—C1—C2	−0.5 (2)	N3—N2—C5—O1	1.6 (3)
N1—C1—C2—C3	0.2 (2)	N3—N2—C5—C4	−177.42 (17)
C1—C2—C3—C4	0.2 (2)	N1—C4—C5—O1	−4.4 (3)
C1—N1—C4—C3	0.6 (2)	C3—C4—C5—O1	175.93 (18)
C1—N1—C4—C5	−179.09 (15)	N1—C4—C5—N2	174.58 (16)
C2—C3—C4—N1	−0.5 (2)	C3—C4—C5—N2	−5.1 (3)
C2—C3—C4—C5	179.19 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.86	2.15	2.996 (2)	169
N2—H2···O1ii	0.86	2.06	2.8422 (19)	151
N3—H3B···O1iii	0.91 (3)	2.12 (3)	3.023 (3)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.86	2.15	2.996 (2)	169
N2—H2⋯O1ii	0.86	2.06	2.8422 (19)	151
N3—H3B⋯O1iii	0.91 (3)	2.12 (3)	3.023 (3)	168 (2)

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