N-Nitro-1H-pyrrole-2-carboxamide.

In the title compound, C(5)H(5)N(3)O(3), the nitro group is twisted with respect to the amide group, with C-N-N-O torsion angles of 29.0 (2) and -153.66 (14)°. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming supra-molecular chains along the a axis. These chains stack in parallel and form distinct layer motifs in the (001) plane.

Related literature

For applications of pyrrole derivatives as anti­microbials, see: Mohamed et al. (2009 ▶). For the structures of similar pyrrole derivatives, see: Zeng et al. (2007 ▶, 2010 ▶); Wang et al. (2010 ▶); Ferreira et al. (2002 ▶). For the synthesis of N,N′-dinitro­urea (DNU), see: Goede et al. (2001 ▶).

Experimental

Crystal data

C5H5N3O3

M = 155.12

Orthorhombic,

a = 9.988 (3) Å

b = 6.4547 (17) Å

c = 19.184 (6) Å

V = 1236.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.14 mm−1

T = 133 K

0.47 × 0.43 × 0.20 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

8849 measured reflections

1402 independent reflections

1214 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.106

S = 1.00

1402 reflections

108 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002455/fj2382sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002455/fj2382Isup2.hkl

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

C5H5N3O3	F(000) = 640
Mr = 155.12	Dx = 1.666 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3166 reflections
a = 9.988 (3) Å	θ = 3.2–27.5°
b = 6.4547 (17) Å	µ = 0.14 mm−1
c = 19.184 (6) Å	T = 133 K
V = 1236.8 (6) Å3	Platelet, colourless
Z = 8	0.47 × 0.43 × 0.20 mm

Rigaku AFC10/Saturn724+ diffractometer	1214 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.034
graphite	θmax = 27.5°, θmin = 3.9°
Detector resolution: 28.5714 pixels mm-1	h = −12→12
φ and ω scans	k = −8→8
8849 measured reflections	l = −24→24
1402 independent reflections

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) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.536P] where P = (Fo2 + 2Fc2)/3
1402 reflections	(Δ/σ)max < 0.001
108 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.15 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
O1	0.17512 (12)	0.34028 (18)	0.50500 (5)	0.0219 (3)
O2	0.27334 (11)	0.3909 (2)	0.37665 (6)	0.0256 (3)
O3	0.45611 (12)	0.21230 (19)	0.36431 (6)	0.0255 (3)
N1	0.25340 (14)	0.3489 (2)	0.64493 (7)	0.0207 (3)
N2	0.39562 (13)	0.3045 (2)	0.47037 (7)	0.0182 (3)
N3	0.37143 (13)	0.3012 (2)	0.39910 (7)	0.0178 (3)
C1	0.31849 (18)	0.3310 (3)	0.70652 (8)	0.0235 (4)
H1	0.2800	0.3496	0.7514	0.028*
C2	0.44956 (17)	0.2815 (3)	0.69312 (8)	0.0240 (4)
H2	0.5173	0.2581	0.7270	0.029*
C3	0.46594 (16)	0.2715 (2)	0.62056 (8)	0.0198 (4)
H3	0.5464	0.2417	0.5962	0.024*
C4	0.34176 (15)	0.3137 (2)	0.59132 (8)	0.0160 (3)
C5	0.29335 (15)	0.3204 (2)	0.52027 (8)	0.0158 (3)
H1N	0.169 (3)	0.380 (4)	0.6375 (12)	0.049 (7)*
H2N	0.474 (2)	0.250 (3)	0.4794 (11)	0.032 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0140 (6)	0.0339 (7)	0.0177 (5)	−0.0002 (5)	−0.0004 (4)	0.0003 (5)
O2	0.0181 (6)	0.0398 (7)	0.0188 (6)	0.0049 (5)	−0.0022 (4)	0.0071 (5)
O3	0.0198 (6)	0.0381 (7)	0.0187 (6)	0.0050 (5)	0.0027 (5)	−0.0052 (5)
N1	0.0164 (7)	0.0276 (7)	0.0180 (6)	0.0021 (6)	0.0007 (5)	0.0002 (6)
N2	0.0132 (6)	0.0281 (7)	0.0133 (6)	0.0016 (5)	−0.0022 (5)	0.0011 (5)
N3	0.0153 (6)	0.0241 (7)	0.0141 (6)	−0.0022 (5)	0.0004 (5)	0.0013 (5)
C1	0.0273 (9)	0.0286 (9)	0.0145 (7)	−0.0002 (7)	0.0011 (6)	0.0000 (6)
C2	0.0223 (8)	0.0315 (9)	0.0183 (8)	−0.0013 (7)	−0.0053 (6)	0.0015 (6)
C3	0.0146 (7)	0.0257 (8)	0.0191 (8)	−0.0008 (6)	−0.0001 (6)	0.0010 (6)
C4	0.0147 (7)	0.0176 (7)	0.0158 (7)	−0.0013 (6)	0.0003 (6)	−0.0001 (5)
C5	0.0148 (7)	0.0164 (7)	0.0163 (7)	−0.0011 (6)	−0.0002 (5)	−0.0002 (6)

O1—C5	1.2234 (19)	N2—H2N	0.88 (2)
O2—N3	1.2167 (17)	C1—C2	1.372 (2)
O3—N3	1.2206 (17)	C1—H1	0.9500
N1—C1	1.354 (2)	C2—C3	1.403 (2)
N1—C4	1.374 (2)	C2—H2	0.9500
N1—H1N	0.88 (3)	C3—C4	1.388 (2)
N2—N3	1.3886 (18)	C3—H3	0.9500
N2—C5	1.404 (2)	C4—C5	1.447 (2)
C1—N1—C4	109.32 (14)	C1—C2—C3	107.93 (15)
C1—N1—H1N	128.4 (16)	C1—C2—H2	126.0
C4—N1—H1N	122.3 (16)	C3—C2—H2	126.0
N3—N2—C5	123.09 (13)	C4—C3—C2	106.72 (14)
N3—N2—H2N	110.2 (14)	C4—C3—H3	126.6
C5—N2—H2N	123.1 (14)	C2—C3—H3	126.6
O2—N3—O3	126.02 (14)	N1—C4—C3	107.68 (13)
O2—N3—N2	118.77 (13)	N1—C4—C5	119.04 (14)
O3—N3—N2	115.15 (13)	C3—C4—C5	133.25 (14)
N1—C1—C2	108.33 (14)	O1—C5—N2	123.14 (14)
N1—C1—H1	125.8	O1—C5—C4	123.46 (14)
C2—C1—H1	125.8	N2—C5—C4	113.39 (13)
C5—N2—N3—O2	29.0 (2)	C2—C3—C4—C5	−177.88 (16)
C5—N2—N3—O3	−153.66 (14)	N3—N2—C5—O1	−2.7 (2)
C4—N1—C1—C2	−0.71 (19)	N3—N2—C5—C4	177.98 (13)
N1—C1—C2—C3	0.9 (2)	N1—C4—C5—O1	−5.8 (2)
C1—C2—C3—C4	−0.67 (19)	C3—C4—C5—O1	172.13 (17)
C1—N1—C4—C3	0.28 (18)	N1—C4—C5—N2	173.46 (13)
C1—N1—C4—C5	178.72 (14)	C3—C4—C5—N2	−8.6 (3)
C2—C3—C4—N1	0.24 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.88 (3)	2.21 (3)	3.001 (2)	150 (2)
N2—H2N···O1ii	0.88 (2)	2.11 (2)	2.982 (2)	171.5 (19)
C3—H3···O1ii	0.95	2.39	3.269 (2)	154
C3—H3···O2ii	0.95	2.48	3.245 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.88 (3)	2.21 (3)	3.001 (2)	150 (2)
N2—H2N⋯O1ii	0.88 (2)	2.11 (2)	2.982 (2)	171.5 (19)
C3—H3⋯O1ii	0.95	2.39	3.269 (2)	154
C3—H3⋯O2ii	0.95	2.48	3.245 (2)	138

Symmetry codes: (i) ; (ii) .