5-Amino-1-(4-nitro-phen-yl)-1H-pyrazole-3-carbonitrile.

The title compound, C(10)H(7)N(5)O(2), was synthesized by the reaction of 4-nitro-aniline and 2,3-dicyano-propionic acid ethyl ester. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network.

Related literature

N-pyrazole derivatives are of great inter­est because of their chemical and pharmaceutical properties, see: Cheng et al. (2008 ▶). They also exhibit diverse biological activity such as insecticidal (Zhao et al., 2010 ▶) and anti­fungal activities (Liu et al., 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H7N5O2

M = 229.21

Monoclinic,

a = 3.7685 (2) Å

b = 27.3441 (17) Å

c = 10.1294 (8) Å

β = 96.20 (3)°

V = 1037.70 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.30 × 0.10 mm

Data collection

Enaf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.968, T max = 0.989

2148 measured reflections

951 independent reflections

856 reflections with I > 2σ(I)

R int = 0.071

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.123

S = 1.00

951 reflections

155 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052147/hg5146sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052147/hg5146Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052147/hg5146Isup3.cml

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

C10H7N5O2	F(000) = 472
Mr = 229.21	Dx = 1.467 Mg m−3
Monoclinic, Cc	Melting point = 498–501 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 3.7685 (2) Å	Cell parameters from 25 reflections
b = 27.3441 (17) Å	θ = 9–13°
c = 10.1294 (8) Å	µ = 0.11 mm−1
β = 96.20 (3)°	T = 293 K
V = 1037.70 (12) Å3	Block, yellow
Z = 4	0.30 × 0.30 × 0.10 mm

Enaf–Nonius CAD-4 diffractometer	856 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
graphite	θmax = 25.4°, θmin = 2.5°
ω/2θ scans	h = 0→4
Absorption correction: ψ scan (North et al., 1968)	k = −32→32
Tmin = 0.968, Tmax = 0.989	l = −12→12
2148 measured reflections	3 standard reflections every 200 reflections
951 independent reflections	intensity decay: 1%

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.093P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
951 reflections	Δρmax = 0.26 e Å−3
155 parameters	Δρmin = −0.31 e Å−3
2 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: 0.017 (6)

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
C1	0.6000 (9)	0.14112 (13)	0.7685 (3)	0.0345 (8)
H1A	0.6497	0.1737	0.7890	0.041*
N1	0.7783 (9)	0.01800 (13)	0.9127 (4)	0.0495 (9)
O1	0.9593 (11)	0.02857 (14)	1.0134 (4)	0.0782 (13)
N2	0.2632 (8)	0.16762 (10)	0.5653 (3)	0.0343 (7)
C2	0.7254 (10)	0.10486 (14)	0.8562 (4)	0.0370 (8)
H2A	0.8616	0.1124	0.9357	0.044*
O2	0.6973 (13)	−0.02441 (11)	0.8819 (4)	0.0763 (12)
C3	0.6406 (9)	0.05648 (13)	0.8214 (3)	0.0347 (8)
N3	0.1670 (9)	0.21026 (11)	0.6233 (3)	0.0362 (7)
C4	0.4432 (9)	0.04433 (12)	0.7061 (4)	0.0361 (8)
H4A	0.3940	0.0117	0.6858	0.043*
N4	0.2620 (12)	0.13064 (12)	0.3498 (3)	0.0517 (9)
H4B	0.3581	0.1043	0.3834	0.062*
H4C	0.2109	0.1331	0.2652	0.062*
C5	0.3155 (9)	0.08073 (14)	0.6189 (3)	0.0353 (8)
H5A	0.1748	0.0731	0.5405	0.042*
N5	−0.2189 (12)	0.32149 (13)	0.5701 (4)	0.0571 (10)
C6	0.4020 (9)	0.12921 (12)	0.6510 (4)	0.0316 (7)
C7	0.1906 (10)	0.16856 (13)	0.4306 (4)	0.0367 (8)
C8	0.0411 (12)	0.21334 (14)	0.3985 (4)	0.0412 (8)
H8A	−0.0359	0.2255	0.3146	0.049*
C9	0.0310 (9)	0.23653 (12)	0.5213 (4)	0.0347 (8)
C10	−0.1059 (10)	0.28392 (14)	0.5470 (4)	0.0411 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0409 (17)	0.0288 (16)	0.0351 (16)	−0.0030 (14)	0.0102 (15)	−0.0032 (14)
N1	0.050 (2)	0.0475 (19)	0.053 (2)	0.0072 (16)	0.0127 (18)	0.0160 (16)
O1	0.094 (3)	0.070 (2)	0.065 (2)	0.005 (2)	−0.021 (2)	0.0227 (19)
N2	0.0461 (16)	0.0256 (14)	0.0317 (14)	0.0020 (13)	0.0072 (12)	0.0000 (12)
C2	0.0424 (18)	0.0389 (18)	0.0305 (16)	0.0005 (16)	0.0073 (14)	0.0026 (14)
O2	0.111 (3)	0.0379 (17)	0.079 (2)	0.0041 (19)	0.010 (2)	0.0194 (16)
C3	0.0330 (17)	0.0337 (17)	0.0394 (17)	0.0046 (15)	0.0129 (15)	0.0066 (15)
N3	0.0488 (17)	0.0255 (14)	0.0357 (15)	0.0032 (12)	0.0108 (13)	−0.0018 (10)
C4	0.0400 (19)	0.0275 (17)	0.0427 (18)	0.0031 (14)	0.0135 (16)	0.0008 (14)
N4	0.090 (3)	0.0352 (16)	0.0300 (14)	0.0101 (17)	0.0084 (16)	−0.0028 (12)
C5	0.0416 (19)	0.0306 (18)	0.0340 (17)	−0.0001 (14)	0.0053 (15)	−0.0029 (12)
N5	0.080 (3)	0.0384 (18)	0.055 (2)	0.0178 (19)	0.0208 (19)	0.0037 (16)
C6	0.0351 (16)	0.0261 (15)	0.0360 (17)	0.0022 (14)	0.0145 (14)	0.0033 (13)
C7	0.0441 (19)	0.0337 (17)	0.0332 (16)	−0.0010 (15)	0.0091 (15)	0.0011 (14)
C8	0.050 (2)	0.0407 (18)	0.0330 (17)	0.0015 (16)	0.0047 (15)	0.0086 (14)
C9	0.0379 (18)	0.0289 (17)	0.0383 (17)	0.0014 (15)	0.0090 (14)	0.0023 (13)
C10	0.049 (2)	0.036 (2)	0.0410 (19)	0.0059 (17)	0.0150 (17)	0.0075 (15)

C1—C6	1.374 (5)	C4—C5	1.382 (5)
C1—C2	1.381 (5)	C4—H4A	0.9300
C1—H1A	0.9300	N4—C7	1.366 (5)
N1—O1	1.199 (5)	N4—H4B	0.8600
N1—O2	1.231 (5)	N4—H4C	0.8600
N1—C3	1.459 (5)	C5—C6	1.395 (5)
N2—C7	1.363 (5)	C5—H5A	0.9300
N2—N3	1.371 (4)	N5—C10	1.146 (5)
N2—C6	1.425 (4)	C7—C8	1.372 (5)
C2—C3	1.397 (5)	C8—C9	1.400 (5)
C2—H2A	0.9300	C8—H8A	0.9300
C3—C4	1.357 (5)	C9—C10	1.429 (5)
N3—C9	1.316 (5)
C6—C1—C2	120.2 (3)	C7—N4—H4B	120.0
C6—C1—H1A	119.9	C7—N4—H4C	120.0
C2—C1—H1A	119.9	H4B—N4—H4C	120.0
O1—N1—O2	123.1 (4)	C4—C5—C6	118.6 (3)
O1—N1—C3	119.7 (4)	C4—C5—H5A	120.7
O2—N1—C3	117.2 (4)	C6—C5—H5A	120.7
C7—N2—N3	112.3 (3)	C1—C6—C5	121.2 (3)
C7—N2—C6	130.1 (3)	C1—C6—N2	118.8 (3)
N3—N2—C6	117.6 (3)	C5—C6—N2	119.8 (3)
C1—C2—C3	117.7 (3)	N2—C7—N4	123.7 (3)
C1—C2—H2A	121.2	N2—C7—C8	106.7 (3)
C3—C2—H2A	121.2	N4—C7—C8	129.6 (4)
C4—C3—C2	122.6 (3)	C7—C8—C9	104.1 (3)
C4—C3—N1	119.6 (3)	C7—C8—H8A	128.0
C2—C3—N1	117.8 (3)	C9—C8—H8A	128.0
C9—N3—N2	103.1 (3)	N3—C9—C8	113.9 (3)
C3—C4—C5	119.6 (3)	N3—C9—C10	118.0 (3)
C3—C4—H4A	120.2	C8—C9—C10	128.2 (3)
C5—C4—H4A	120.2	N5—C10—C9	178.4 (4)
C6—C1—C2—C3	−0.6 (5)	C4—C5—C6—N2	−177.7 (3)
C1—C2—C3—C4	0.1 (5)	C7—N2—C6—C1	150.6 (4)
C1—C2—C3—N1	178.9 (3)	N3—N2—C6—C1	−33.0 (5)
O1—N1—C3—C4	178.4 (4)	C7—N2—C6—C5	−33.7 (6)
O2—N1—C3—C4	−2.3 (5)	N3—N2—C6—C5	142.6 (3)
O1—N1—C3—C2	−0.4 (5)	N3—N2—C7—N4	179.8 (4)
O2—N1—C3—C2	178.9 (4)	C6—N2—C7—N4	−3.7 (6)
C7—N2—N3—C9	0.8 (4)	N3—N2—C7—C8	−0.1 (4)
C6—N2—N3—C9	−176.1 (3)	C6—N2—C7—C8	176.4 (4)
C2—C3—C4—C5	−0.7 (5)	N2—C7—C8—C9	−0.7 (4)
N1—C3—C4—C5	−179.4 (3)	N4—C7—C8—C9	179.4 (4)
C3—C4—C5—C6	1.6 (5)	N2—N3—C9—C8	−1.3 (4)
C2—C1—C6—C5	1.6 (5)	N2—N3—C9—C10	178.7 (3)
C2—C1—C6—N2	177.2 (3)	C7—C8—C9—N3	1.3 (5)
C4—C5—C6—C1	−2.1 (5)	C7—C8—C9—C10	−178.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O2i	0.86	2.53	3.335 (5)	156.
C4—H4A···O1ii	0.93	2.52	3.216 (5)	132.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O2i	0.86	2.53	3.335 (5)	156
C4—H4A⋯O1ii	0.93	2.52	3.216 (5)	132

Symmetry codes: (i) ; (ii) .