(E)-3-Amino-4-(2-phenyl-hydrazinyl-idene)-1H-pyrazol-5(4H)-one.

The mol-ecule of the title compound, C(9)H(9)N(5)O, is essentially planar (r.m.s. deviation of all atoms = 0.02 Å) except for the NH(2) H atoms. An intra-molecular hydrazinyl-idene-carbonyl N-H⋯O=C hydrogen bond is present. In the crystal, mol-ecules are connected via N-H⋯N/O hydrogen bonds, forming thick layers parallel to (100).

Related literature

The synthesis, chemistry and biological/medical activity of related compounds is described in: Elgemeie (2003 ▶); Elgemeie & El-Aziz (2002 ▶); Elgemeie & Sood (2003 ▶, 2006 ▶); Elgemeie et al. (2001 ▶, 2007 ▶, 2008 ▶, 2009 ▶).

Experimental

Crystal data

C9H9N5O

M = 203.21

Monoclinic,

a = 6.7380 (2) Å

b = 13.4310 (4) Å

c = 10.4563 (3) Å

β = 103.094 (3)°

V = 921.67 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.86 mm−1

T = 100 K

0.15 × 0.10 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.668, T max = 1.000

26682 measured reflections

1914 independent reflections

1807 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 1.05

1914 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050854/gg2105sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050854/gg2105Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050854/gg2105Isup3.cml

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

C9H9N5O	F(000) = 424
Mr = 203.21	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Melting point: 518 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 6.7380 (2) Å	Cell parameters from 18413 reflections
b = 13.4310 (4) Å	θ = 3.3–75.6°
c = 10.4563 (3) Å	µ = 0.86 mm−1
β = 103.094 (3)°	T = 100 K
V = 921.67 (5) Å3	Tablet, orange-brown
Z = 4	0.15 × 0.10 × 0.03 mm

Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer	1914 independent reflections
Radiation source: Nova (Cu) X-ray Source	1807 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.3543 pixels mm-1	θmax = 75.8°, θmin = 5.5°
ω–scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −16→16
Tmin = 0.668, Tmax = 1.000	l = −13→13
26682 measured 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.2869P] where P = (Fo2 + 2Fc2)/3
1914 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.26 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)- 6.7047 (0.0004) x + 0.5009 (0.0024) y + 3.2946 (0.0013) z = 0.2057 (0.0017)* -0.0265 (0.0007) O1 * -0.0015 (0.0008) N1 * 0.0248 (0.0008) N2 * 0.0064 (0.0007) N3 * -0.0035 (0.0008) N4 * 0.0047 (0.0008) N5 * 0.0127 (0.0009) C3 * -0.0173 (0.0009) C4 * -0.0155 (0.0009) C5 * 0.0096 (0.0009) C11 * 0.0334 (0.0009) C12 * 0.0207 (0.0009) C13 * -0.0104 (0.0009) C14 * -0.0239 (0.0009) C15 * -0.0136 (0.0009) C16 0.3618 (0.0145) H03A 0.2676 (0.0152) H03BRms deviation of fitted atoms = 0.0175

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	0.09284 (11)	0.44649 (5)	0.17545 (7)	0.02234 (19)
N1	0.06030 (14)	0.60858 (6)	0.09217 (8)	0.0210 (2)
H01	0.008 (2)	0.5972 (11)	0.0053 (16)	0.036 (4)*
N2	0.08679 (13)	0.70841 (6)	0.13887 (8)	0.0210 (2)
C3	0.15061 (15)	0.70044 (7)	0.26628 (10)	0.0188 (2)
C4	0.16773 (15)	0.59729 (7)	0.30772 (10)	0.0182 (2)
C5	0.10365 (15)	0.53946 (8)	0.18664 (9)	0.0190 (2)
N3	0.19896 (14)	0.77858 (7)	0.35089 (9)	0.0230 (2)
H03B	0.202 (2)	0.7633 (12)	0.4385 (16)	0.041 (4)*
H03A	0.135 (2)	0.8364 (12)	0.3206 (15)	0.036 (4)*
N4	0.22316 (12)	0.56774 (6)	0.42917 (8)	0.0180 (2)
N5	0.22648 (13)	0.47167 (6)	0.45303 (8)	0.0193 (2)
H05	0.189 (2)	0.4280 (12)	0.3870 (15)	0.034 (4)*
C11	0.28700 (14)	0.43692 (8)	0.58298 (10)	0.0190 (2)
C12	0.28637 (16)	0.33470 (8)	0.60446 (11)	0.0229 (2)
H12	0.2442	0.2901	0.5329	0.028*
C13	0.34813 (16)	0.29858 (8)	0.73178 (11)	0.0268 (3)
H13	0.3487	0.2289	0.7473	0.032*
C14	0.40897 (16)	0.36360 (9)	0.83626 (11)	0.0283 (3)
H14	0.4516	0.3386	0.9232	0.034*
C15	0.40732 (17)	0.46548 (9)	0.81331 (10)	0.0271 (3)
H15	0.4484	0.5099	0.8851	0.033*
C16	0.34645 (16)	0.50330 (8)	0.68682 (10)	0.0223 (2)
H16	0.3454	0.5730	0.6715	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0293 (4)	0.0182 (4)	0.0181 (4)	−0.0032 (3)	0.0024 (3)	−0.0003 (3)
N1	0.0273 (5)	0.0194 (4)	0.0149 (4)	−0.0021 (3)	0.0018 (3)	0.0002 (3)
N2	0.0249 (4)	0.0182 (4)	0.0193 (4)	−0.0005 (3)	0.0038 (3)	0.0006 (3)
C3	0.0188 (5)	0.0190 (5)	0.0189 (5)	0.0015 (4)	0.0045 (4)	0.0008 (4)
C4	0.0188 (5)	0.0189 (5)	0.0166 (5)	0.0006 (4)	0.0036 (4)	−0.0002 (4)
C5	0.0199 (5)	0.0205 (5)	0.0164 (5)	−0.0012 (4)	0.0038 (4)	0.0008 (4)
N3	0.0310 (5)	0.0173 (4)	0.0199 (4)	0.0032 (4)	0.0042 (4)	−0.0004 (3)
N4	0.0190 (4)	0.0179 (4)	0.0172 (4)	0.0019 (3)	0.0042 (3)	0.0012 (3)
N5	0.0237 (4)	0.0178 (4)	0.0155 (4)	0.0001 (3)	0.0028 (3)	−0.0002 (3)
C11	0.0170 (4)	0.0228 (5)	0.0170 (5)	0.0015 (4)	0.0039 (4)	0.0034 (4)
C12	0.0216 (5)	0.0225 (5)	0.0246 (5)	0.0002 (4)	0.0049 (4)	0.0016 (4)
C13	0.0229 (5)	0.0262 (6)	0.0316 (6)	0.0021 (4)	0.0071 (4)	0.0107 (4)
C14	0.0239 (5)	0.0384 (7)	0.0220 (5)	0.0025 (5)	0.0040 (4)	0.0111 (5)
C15	0.0272 (5)	0.0360 (6)	0.0175 (5)	−0.0002 (5)	0.0034 (4)	0.0008 (4)
C16	0.0238 (5)	0.0242 (5)	0.0188 (5)	0.0006 (4)	0.0045 (4)	0.0010 (4)

O1—C5	1.2548 (13)	C13—C14	1.3861 (17)
N1—C5	1.3387 (13)	C14—C15	1.3890 (17)
N1—N2	1.4242 (12)	C15—C16	1.3891 (15)
N2—C3	1.3083 (13)	N1—H01	0.909 (16)
C3—N3	1.3637 (13)	N3—H03B	0.934 (17)
C3—C4	1.4484 (13)	N3—H03A	0.908 (16)
C4—N4	1.3019 (13)	N5—H05	0.897 (16)
C4—C5	1.4645 (13)	C12—H12	0.9500
N4—N5	1.3134 (12)	C13—H13	0.9500
N5—C11	1.4069 (13)	C14—H14	0.9500
C11—C12	1.3914 (15)	C15—H15	0.9500
C11—C16	1.3918 (15)	C16—H16	0.9500
C12—C13	1.3892 (15)
C5—N1—N2	114.23 (8)	C14—C15—C16	120.92 (10)
C3—N2—N1	105.00 (8)	C15—C16—C11	118.64 (10)
N2—C3—N3	124.94 (9)	C5—N1—H01	126.2 (10)
N2—C3—C4	111.62 (9)	N2—N1—H01	119.4 (10)
N3—C3—C4	123.43 (9)	C3—N3—H03B	114.5 (10)
N4—C4—C3	124.69 (9)	C3—N3—H03A	114.0 (9)
N4—C4—C5	130.16 (9)	H03B—N3—H03A	115.7 (14)
C3—C4—C5	105.11 (8)	N4—N5—H05	120.4 (10)
O1—C5—N1	128.54 (9)	C11—N5—H05	119.7 (10)
O1—C5—C4	127.43 (9)	C13—C12—H12	120.4
N1—C5—C4	104.03 (9)	C11—C12—H12	120.4
C4—N4—N5	118.26 (9)	C14—C13—H13	119.8
N4—N5—C11	119.87 (8)	C12—C13—H13	119.8
C12—C11—C16	121.13 (9)	C13—C14—H14	120.2
C12—C11—N5	118.19 (9)	C15—C14—H14	120.2
C16—C11—N5	120.67 (9)	C14—C15—H15	119.5
C13—C12—C11	119.21 (10)	C16—C15—H15	119.5
C14—C13—C12	120.42 (10)	C15—C16—H16	120.7
C13—C14—C15	119.68 (10)	C11—C16—H16	120.7
C5—N1—N2—C3	0.65 (12)	C3—C4—N4—N5	178.06 (9)
N1—N2—C3—N3	178.81 (9)	C5—C4—N4—N5	0.52 (16)
N1—N2—C3—C4	−0.17 (11)	C4—N4—N5—C11	179.53 (9)
N2—C3—C4—N4	−178.34 (9)	N4—N5—C11—C12	179.30 (8)
N3—C3—C4—N4	2.66 (16)	N4—N5—C11—C16	−0.93 (14)
N2—C3—C4—C5	−0.29 (12)	C16—C11—C12—C13	−0.62 (15)
N3—C3—C4—C5	−179.29 (9)	N5—C11—C12—C13	179.15 (9)
N2—N1—C5—O1	179.27 (9)	C11—C12—C13—C14	0.23 (16)
N2—N1—C5—C4	−0.81 (11)	C12—C13—C14—C15	0.24 (16)
N4—C4—C5—O1	−1.54 (18)	C13—C14—C15—C16	−0.33 (17)
C3—C4—C5—O1	−179.44 (10)	C14—C15—C16—C11	−0.05 (16)
N4—C4—C5—N1	178.55 (10)	C12—C11—C16—C15	0.53 (15)
C3—C4—C5—N1	0.65 (10)	N5—C11—C16—C15	−179.24 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1i	0.909 (16)	1.949 (16)	2.8521 (11)	172.0 (14)
N3—H03B···N2ii	0.934 (17)	2.424 (16)	3.2711 (12)	150.8 (13)
N3—H03A···O1iii	0.908 (16)	2.141 (15)	2.9635 (11)	150.2 (13)
N3—H03B···N1ii	0.934 (17)	2.674 (16)	3.2562 (13)	121.1 (12)
N5—H05···O1	0.897 (16)	2.174 (16)	2.8575 (11)	132.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯O1i	0.909 (16)	1.949 (16)	2.8521 (11)	172.0 (14)
N3—H03B⋯N2ii	0.934 (17)	2.424 (16)	3.2711 (12)	150.8 (13)
N3—H03A⋯O1iii	0.908 (16)	2.141 (15)	2.9635 (11)	150.2 (13)
N5—H05⋯O1	0.897 (16)	2.174 (16)	2.8575 (11)	132.5 (13)

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