5-Amino-3-anilino-1H-pyrazole-4-carbonitrile.

In the title compound, C(10)H(9)N(5), the phenyl ring is twisted with respect to the pyrazole ring, forming a dihedral angle of 24.00 (6)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds into chains running parallel to [010] containing alternating R(2) (2)(6) and R(2) (2)(12) rings. Further inter-actions are found in the crystal, viz. N-H⋯π(phen-yl) inter-actions and weak face-to-face π-π stacking inter-actions [centroid-centroid distance = 3.8890 (6) Å] between the centroids of the pyrazole and phenyl rings are observed.

Related literature

For biological activities of pyrazoles, see: Kaushik et al. (2010 ▶); Sheikh et al. (2009 ▶); Krishnamurthy et al. (2004 ▶); Grimmett (1970 ▶). For the use of related compounds as bridging ligands, see: Lynch & McClenaghan (2005 ▶). For the synthesis of the title compound, see: Soliman et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H9N5

M = 199.22

Orthorhombic,

a = 6.3441 (1) Å

b = 11.1354 (2) Å

c = 13.7754 (3) Å

V = 973.15 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.25 × 0.17 × 0.08 mm

Data collection

Bruker Kappa APEXII DUO diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.978, T max = 0.993

32878 measured reflections

2975 independent reflections

2767 reflections with I > 2σ(I)

R int = 0.035

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.09

2975 reflections

152 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036045/tk5143sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036045/tk5143Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036045/tk5143Isup3.cml

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

C10H9N5	F(000) = 416
Mr = 199.22	Dx = 1.360 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9908 reflections
a = 6.3441 (1) Å	θ = 2.4–30.5°
b = 11.1354 (2) Å	µ = 0.09 mm−1
c = 13.7754 (3) Å	T = 90 K
V = 973.15 (3) Å3	Plate, colourless
Z = 4	0.25 × 0.17 × 0.08 mm

Bruker Kappa APEXII DUO diffractometer	2975 independent reflections
Radiation source: fine-focus sealed tube	2767 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 30.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.978, Tmax = 0.993	k = −15→15
32878 measured reflections	l = −19→19

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.1533P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2975 reflections	Δρmax = 0.32 e Å−3
152 parameters	Δρmin = −0.20 e Å−3
4 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.50345 (15)	−0.01004 (8)	0.89839 (7)	0.0142 (2)
N2	0.71282 (15)	0.15769 (8)	0.94613 (7)	0.0154 (2)
N3	0.89266 (15)	0.16812 (8)	1.00299 (7)	0.0168 (2)
N4	1.13973 (17)	0.05235 (10)	1.09010 (8)	0.0234 (3)
N5	0.84875 (15)	−0.24944 (9)	1.03572 (7)	0.0204 (3)
C1	0.40580 (18)	0.15607 (10)	0.78868 (8)	0.0173 (3)
C2	0.2548 (2)	0.20761 (11)	0.72811 (8)	0.0205 (3)
C3	0.06057 (19)	0.15345 (11)	0.71341 (8)	0.0213 (3)
C4	0.01783 (19)	0.04497 (11)	0.75945 (8)	0.0193 (3)
C5	0.16597 (18)	−0.00746 (10)	0.82040 (7)	0.0152 (3)
C6	0.36064 (16)	0.04854 (9)	0.83683 (7)	0.0130 (2)
C7	0.66942 (16)	0.04110 (9)	0.94711 (7)	0.0122 (2)
C8	0.81769 (17)	−0.02408 (9)	1.00460 (8)	0.0133 (2)
C9	0.96026 (17)	0.06332 (10)	1.03764 (8)	0.0153 (3)
C10	0.83277 (17)	−0.14847 (9)	1.02122 (7)	0.0145 (2)
H1	0.53600	0.19300	0.79700	0.0210*
H1N	0.459 (3)	−0.0771 (13)	0.9176 (12)	0.027 (4)*
H2	0.28480	0.27970	0.69700	0.0250*
H3	−0.03960	0.18910	0.67340	0.0260*
H3N	0.958 (3)	0.2358 (13)	1.0116 (14)	0.034 (5)*
H4	−0.11110	0.00720	0.74930	0.0230*
H5	0.13580	−0.08020	0.85050	0.0180*
H11	1.200 (3)	0.1170 (14)	1.1129 (13)	0.038 (5)*
H12	1.165 (3)	−0.0151 (14)	1.1162 (13)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0145 (4)	0.0093 (4)	0.0189 (4)	−0.0012 (3)	−0.0034 (4)	0.0031 (3)
N2	0.0152 (4)	0.0112 (4)	0.0197 (4)	−0.0003 (3)	−0.0030 (3)	−0.0012 (3)
N3	0.0178 (4)	0.0117 (4)	0.0208 (4)	−0.0023 (3)	−0.0038 (3)	−0.0005 (3)
N4	0.0219 (5)	0.0230 (5)	0.0253 (5)	−0.0035 (4)	−0.0095 (4)	0.0041 (4)
N5	0.0189 (5)	0.0160 (4)	0.0262 (5)	0.0023 (4)	0.0001 (4)	0.0038 (4)
C1	0.0189 (5)	0.0150 (5)	0.0179 (5)	−0.0012 (4)	−0.0018 (4)	0.0018 (4)
C2	0.0260 (6)	0.0172 (5)	0.0183 (5)	0.0030 (4)	−0.0029 (4)	0.0044 (4)
C3	0.0206 (5)	0.0250 (6)	0.0182 (5)	0.0068 (5)	−0.0037 (4)	0.0018 (4)
C4	0.0144 (5)	0.0251 (5)	0.0184 (5)	0.0007 (4)	−0.0004 (4)	−0.0010 (4)
C5	0.0134 (5)	0.0170 (4)	0.0153 (4)	−0.0011 (4)	0.0010 (4)	0.0006 (4)
C6	0.0136 (4)	0.0126 (4)	0.0129 (4)	0.0025 (4)	−0.0004 (3)	−0.0002 (3)
C7	0.0124 (4)	0.0105 (4)	0.0137 (4)	0.0007 (4)	0.0005 (4)	0.0003 (3)
C8	0.0128 (4)	0.0126 (4)	0.0145 (4)	0.0008 (3)	0.0001 (4)	0.0011 (3)
C9	0.0157 (4)	0.0155 (5)	0.0147 (4)	−0.0005 (4)	0.0002 (3)	0.0004 (4)
C10	0.0125 (4)	0.0164 (4)	0.0147 (4)	0.0011 (4)	0.0008 (3)	0.0017 (3)

N1—C6	1.4020 (14)	C2—C3	1.3868 (17)
N1—C7	1.3724 (14)	C3—C4	1.3910 (17)
N2—N3	1.3888 (14)	C4—C5	1.3889 (16)
N2—C7	1.3272 (13)	C5—C6	1.4019 (15)
N3—C9	1.3318 (14)	C7—C8	1.4279 (15)
N4—C9	1.3541 (15)	C8—C9	1.4044 (15)
N5—C10	1.1464 (14)	C8—C10	1.4072 (14)
N1—H1N	0.841 (15)	C1—H1	0.9300
N3—H3N	0.868 (16)	C2—H2	0.9300
N4—H11	0.874 (17)	C3—H3	0.9300
N4—H12	0.848 (16)	C4—H4	0.9300
C1—C2	1.3940 (16)	C5—H5	0.9300
C1—C6	1.3985 (15)
C6—N1—C7	126.77 (9)	N1—C7—N2	124.06 (9)
N3—N2—C7	104.27 (8)	N1—C7—C8	124.46 (9)
N2—N3—C9	113.17 (9)	C7—C8—C9	104.58 (9)
C6—N1—H1N	112.8 (13)	C7—C8—C10	129.45 (10)
C7—N1—H1N	118.2 (12)	C9—C8—C10	125.85 (10)
N2—N3—H3N	122.8 (12)	N3—C9—N4	122.76 (10)
C9—N3—H3N	123.9 (12)	N3—C9—C8	106.48 (9)
C9—N4—H12	117.7 (12)	N4—C9—C8	130.69 (11)
H11—N4—H12	119.7 (17)	N5—C10—C8	178.64 (11)
C9—N4—H11	119.1 (12)	C2—C1—H1	120.00
C2—C1—C6	119.71 (10)	C6—C1—H1	120.00
C1—C2—C3	121.26 (11)	C1—C2—H2	119.00
C2—C3—C4	118.97 (11)	C3—C2—H2	119.00
C3—C4—C5	120.58 (11)	C2—C3—H3	121.00
C4—C5—C6	120.45 (10)	C4—C3—H3	121.00
N1—C6—C1	123.57 (9)	C3—C4—H4	120.00
N1—C6—C5	117.39 (9)	C5—C4—H4	120.00
C1—C6—C5	119.00 (9)	C4—C5—H5	120.00
N2—C7—C8	111.48 (9)	C6—C5—H5	120.00
C7—N1—C6—C5	−159.01 (10)	C2—C3—C4—C5	0.99 (17)
C6—N1—C7—N2	3.39 (17)	C3—C4—C5—C6	0.32 (16)
C7—N1—C6—C1	23.65 (16)	C4—C5—C6—C1	−1.90 (15)
C6—N1—C7—C8	−176.20 (10)	C4—C5—C6—N1	−179.36 (10)
C7—N2—N3—C9	0.38 (12)	N1—C7—C8—C9	178.44 (10)
N3—N2—C7—C8	0.53 (12)	N2—C7—C8—C10	−177.26 (11)
N3—N2—C7—N1	−179.10 (10)	N1—C7—C8—C10	2.37 (18)
N2—N3—C9—N4	176.12 (10)	N2—C7—C8—C9	−1.19 (12)
N2—N3—C9—C8	−1.13 (13)	C7—C8—C9—N3	1.35 (12)
C6—C1—C2—C3	−0.88 (17)	C10—C8—C9—N4	0.7 (2)
C2—C1—C6—N1	179.46 (10)	C7—C8—C9—N4	−175.60 (12)
C2—C1—C6—C5	2.16 (16)	C10—C8—C9—N3	177.60 (10)
C1—C2—C3—C4	−0.71 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N5i	0.84 (2)	2.15 (2)	2.9934 (13)	179 (2)
N3—H3N···N2ii	0.87 (2)	2.09 (2)	2.8947 (13)	154 (2)
C1—H1···N2	0.93	2.37	2.9152 (15)	117
N4—H12···Cg2iii	0.85 (2)	2.51 (2)	3.2011 (12)	140 (2)

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N5i	0.84 (2)	2.15 (2)	2.9934 (13)	179 (2)
N3—H3N⋯N2ii	0.87 (2)	2.09 (2)	2.8947 (13)	154 (2)
N4—H12⋯Cg2iii	0.85 (2)	2.51 (2)	3.2011 (12)	140 (2)

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