3-Amino-1-phenyl-4-(propan-2-yl-idene)pyrazol-5(4H)-one.

In the title mol-ecule, C(12)H(13)N(3)O, the phenyl and the pyrazole rings make a dihedral angle of 7.5 (2)°. Inter-molecular N-H⋯O hydrogen bonds involving the amino group link the mol-ecules into a three-dimensional framework.

Related literature

For a related structure, see: Wang et al. (2003 ▶). For applications of pyrazolone derivatives, see: Hodnett et al. (1972 ▶).

Experimental

Crystal data

C12H13N3O

M = 215.25

Orthorhombic,

a = 22.557 (8) Å

b = 26.291 (9) Å

c = 7.528 (3) Å

V = 4465 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 273 (2) K

0.15 × 0.12 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.987, T max = 0.993

7064 measured reflections

1448 independent reflections

960 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.138

S = 1.03

1448 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063234/ci2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063234/ci2526Isup2.hkl

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

C12H13N3O	F000 = 1824
Mr = 215.25	Dx = 1.281 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 1182 reflections
a = 22.557 (8) Å	θ = 3.0–21.1º
b = 26.291 (9) Å	µ = 0.09 mm−1
c = 7.528 (3) Å	T = 273 (2) K
V = 4465 (3) Å3	Block, orange
Z = 16	0.15 × 0.12 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	1448 independent reflections
Radiation source: sealed tube	960 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 273(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −30→30
Tmin = 0.987, Tmax = 0.993	k = −35→35
7064 measured reflections	l = −10→10

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0788P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
1448 reflections	Δρmax = 0.15 e Å−3
147 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.42250 (10)	0.19174 (8)	0.4851 (4)	0.0682 (8)
N1	0.48595 (11)	0.12402 (8)	0.4474 (4)	0.0491 (7)
N2	0.48444 (12)	0.07007 (8)	0.4631 (4)	0.0527 (7)
N3	0.41722 (12)	0.00919 (9)	0.5431 (5)	0.0677 (9)
H3A	0.4432	−0.0143	0.5262	0.081*
H3B	0.3821	0.0013	0.5779	0.081*
C1	0.43317 (14)	0.14594 (11)	0.4913 (5)	0.0493 (8)
C2	0.39362 (13)	0.10311 (10)	0.5399 (5)	0.0461 (8)
C3	0.43167 (14)	0.05839 (10)	0.5153 (5)	0.0484 (8)
C4	0.33718 (14)	0.10759 (11)	0.5946 (5)	0.0496 (8)
C5	0.30732 (16)	0.15770 (12)	0.6224 (6)	0.0622 (10)
H5A	0.3365	0.1842	0.6240	0.093*
H5B	0.2865	0.1573	0.7335	0.093*
H5C	0.2798	0.1637	0.5275	0.093*
C6	0.29806 (16)	0.06265 (13)	0.6325 (7)	0.0685 (12)
H6A	0.2930	0.0431	0.5260	0.103*
H6B	0.2601	0.0743	0.6733	0.103*
H6C	0.3161	0.0419	0.7224	0.103*
C7	0.53990 (13)	0.14704 (11)	0.3951 (5)	0.0471 (7)
C8	0.58725 (15)	0.11694 (14)	0.3435 (5)	0.0605 (9)
H8	0.5833	0.0817	0.3398	0.073*
C9	0.64021 (17)	0.13950 (15)	0.2978 (6)	0.0740 (12)
H9	0.6719	0.1192	0.2633	0.089*
C10	0.64711 (18)	0.19102 (16)	0.3021 (7)	0.0776 (12)
H10	0.6831	0.2058	0.2707	0.093*
C11	0.60048 (16)	0.22050 (14)	0.3530 (7)	0.0731 (12)
H11	0.6049	0.2557	0.3554	0.088*
C12	0.54684 (16)	0.19944 (13)	0.4011 (6)	0.0605 (10)
H12	0.5156	0.2201	0.4371	0.073*

	U11	U22	U33	U12	U13	U23
O1	0.0507 (13)	0.0357 (12)	0.118 (2)	0.0070 (9)	0.0051 (14)	0.0085 (12)
N1	0.0397 (14)	0.0350 (12)	0.0728 (19)	0.0038 (10)	−0.0001 (12)	0.0076 (13)
N2	0.0485 (15)	0.0354 (12)	0.074 (2)	0.0030 (11)	0.0015 (14)	0.0035 (13)
N3	0.0574 (17)	0.0351 (14)	0.111 (3)	0.0070 (12)	0.0143 (18)	0.0088 (15)
C1	0.0438 (17)	0.0390 (16)	0.065 (2)	0.0028 (12)	−0.0009 (16)	0.0060 (14)
C2	0.0464 (17)	0.0345 (14)	0.057 (2)	0.0027 (13)	−0.0045 (15)	0.0042 (14)
C3	0.0477 (18)	0.0341 (15)	0.063 (2)	0.0035 (12)	0.0000 (16)	0.0032 (14)
C4	0.0442 (18)	0.0455 (17)	0.059 (2)	0.0041 (13)	0.0001 (15)	0.0060 (14)
C5	0.053 (2)	0.053 (2)	0.081 (3)	0.0102 (15)	0.006 (2)	0.0052 (18)
C6	0.051 (2)	0.055 (2)	0.099 (3)	−0.0012 (15)	0.012 (2)	0.012 (2)
C7	0.0413 (17)	0.0493 (17)	0.0508 (19)	0.0001 (13)	−0.0011 (15)	0.0080 (16)
C8	0.056 (2)	0.0558 (19)	0.070 (3)	0.0046 (16)	0.0082 (19)	0.0041 (17)
C9	0.052 (2)	0.081 (3)	0.090 (3)	0.004 (2)	0.023 (2)	0.008 (2)
C10	0.053 (2)	0.082 (3)	0.098 (3)	−0.0153 (19)	0.016 (2)	0.009 (2)
C11	0.061 (2)	0.057 (2)	0.101 (3)	−0.0129 (17)	0.006 (2)	0.009 (2)
C12	0.052 (2)	0.0498 (19)	0.080 (3)	0.0001 (14)	0.0046 (18)	0.0082 (18)

O1—C1	1.229 (3)	C5—H5C	0.96
N1—C1	1.363 (4)	C6—H6A	0.96
N1—C7	1.415 (4)	C6—H6B	0.96
N1—N2	1.424 (3)	C6—H6C	0.96
N2—C3	1.290 (4)	C7—C8	1.385 (5)
N3—C3	1.350 (4)	C7—C12	1.387 (4)
N3—H3A	0.86	C8—C9	1.377 (5)
N3—H3B	0.86	C8—H8	0.93
C1—C2	1.482 (4)	C9—C10	1.364 (5)
C2—C4	1.343 (4)	C9—H9	0.93
C2—C3	1.468 (4)	C10—C11	1.362 (6)
C4—C5	1.494 (4)	C10—H10	0.93
C4—C6	1.502 (5)	C11—C12	1.379 (5)
C5—H5A	0.96	C11—H11	0.93
C5—H5B	0.96	C12—H12	0.93
C1—N1—C7	129.6 (2)	C4—C6—H6A	109.5
C1—N1—N2	112.3 (2)	C4—C6—H6B	109.5
C7—N1—N2	118.0 (2)	H6A—C6—H6B	109.5
C3—N2—N1	106.5 (2)	C4—C6—H6C	109.5
C3—N3—H3A	120.0	H6A—C6—H6C	109.5
C3—N3—H3B	120.0	H6B—C6—H6C	109.5
H3A—N3—H3B	120.0	C8—C7—C12	119.3 (3)
O1—C1—N1	125.2 (3)	C8—C7—N1	119.8 (3)
O1—C1—C2	129.5 (3)	C12—C7—N1	120.8 (3)
N1—C1—C2	105.3 (2)	C9—C8—C7	119.5 (3)
C4—C2—C3	131.6 (3)	C9—C8—H8	120.2
C4—C2—C1	125.4 (3)	C7—C8—H8	120.2
C3—C2—C1	103.0 (3)	C10—C9—C8	121.4 (3)
N2—C3—N3	119.9 (3)	C10—C9—H9	119.3
N2—C3—C2	112.8 (2)	C8—C9—H9	119.3
N3—C3—C2	127.3 (3)	C11—C10—C9	118.9 (3)
C2—C4—C5	123.2 (3)	C11—C10—H10	120.5
C2—C4—C6	123.1 (3)	C9—C10—H10	120.5
C5—C4—C6	113.7 (3)	C10—C11—C12	121.5 (4)
C4—C5—H5A	109.5	C10—C11—H11	119.2
C4—C5—H5B	109.5	C12—C11—H11	119.2
H5A—C5—H5B	109.5	C11—C12—C7	119.3 (3)
C4—C5—H5C	109.5	C11—C12—H12	120.4
H5A—C5—H5C	109.5	C7—C12—H12	120.4
H5B—C5—H5C	109.5
C1—N1—N2—C3	0.2 (4)	C3—C2—C4—C5	175.8 (4)
C7—N1—N2—C3	178.7 (3)	C1—C2—C4—C5	−3.1 (5)
C7—N1—C1—O1	3.4 (6)	C3—C2—C4—C6	−4.6 (6)
N2—N1—C1—O1	−178.3 (3)	C1—C2—C4—C6	176.5 (4)
C7—N1—C1—C2	−178.3 (3)	C1—N1—C7—C8	−175.2 (4)
N2—N1—C1—C2	0.0 (4)	N2—N1—C7—C8	6.5 (5)
O1—C1—C2—C4	−2.8 (6)	C1—N1—C7—C12	7.3 (6)
N1—C1—C2—C4	179.0 (3)	N2—N1—C7—C12	−171.0 (3)
O1—C1—C2—C3	178.0 (4)	C12—C7—C8—C9	−0.5 (6)
N1—C1—C2—C3	−0.2 (4)	N1—C7—C8—C9	−178.1 (4)
N1—N2—C3—N3	−179.5 (3)	C7—C8—C9—C10	0.0 (7)
N1—N2—C3—C2	−0.3 (4)	C8—C9—C10—C11	0.1 (8)
C4—C2—C3—N2	−178.8 (4)	C9—C10—C11—C12	0.4 (8)
C1—C2—C3—N2	0.3 (4)	C10—C11—C12—C7	−0.9 (7)
C4—C2—C3—N3	0.3 (6)	C8—C7—C12—C11	1.0 (6)
C1—C2—C3—N3	179.4 (3)	N1—C7—C12—C11	178.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2i	0.86	2.25	3.105 (3)	174
N3—H3B···O1ii	0.86	2.32	3.054 (3)	144
C5—H5A···O1	0.96	2.20	2.935 (5)	131
C12—H12···O1	0.93	2.26	2.882 (4)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N2i	0.86	2.25	3.105 (3)	174
N3—H3B⋯O1ii	0.86	2.32	3.054 (3)	144
C5—H5A⋯O1	0.96	2.20	2.935 (5)	131
C12—H12⋯O1	0.93	2.26	2.882 (4)	124

Symmetry codes: (i) ; (ii) .