3-(3,5-Dimethyl-1H-pyrazol-1-yl)propanamide.

In the crystal of the title compound, C(8)H(13)N(3)O, mol-ecules are linked by inter-molecular N-H⋯N and N-H⋯O hydrogen bonds into a three-dimensional network. Additional stabilization is provided by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the potential applications of hemilabile ligands containing substituted pyrazole groups, see: Pal et al. (2005 ▶); Shaw et al. (2004 ▶). For the design of various pyrazole ligands with special structural properties to fulfill the specific stereochemical requirement of a particular metal-binding site, see: Mukherjee (2000 ▶); Paul et al. (2004 ▶);

Experimental

Crystal data

C8H13N3O

M = 167.21

Orthorhombic,

a = 14.452 (5) Å

b = 33.390 (7) Å

c = 7.4354 (15) Å

V = 3588.0 (16) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.47 × 0.37 × 0.36 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.963, T max = 0.970

4623 measured reflections

1067 independent reflections

890 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.093

S = 1.14

1067 reflections

112 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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 datablocks global, I. DOI: 10.1107/S160053680903342X/lh2847sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903342X/lh2847Isup2.hkl

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

C8H13N3O	F(000) = 1440
Mr = 167.21	Dx = 1.238 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 4623 reflections
a = 14.452 (5) Å	θ = 3.1–27.5°
b = 33.390 (7) Å	µ = 0.09 mm−1
c = 7.4354 (15) Å	T = 298 K
V = 3588.0 (16) Å3	Block, colorless
Z = 16	0.47 × 0.37 × 0.36 mm

Rigaku R-AXIS RAPID diffractometer	1067 independent reflections
Radiation source: fine-focus sealed tube	890 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −17→18
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −43→43
Tmin = 0.963, Tmax = 0.970	l = −9→8
4623 measured reflections

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-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0446P)2 + 1.8694P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
1067 reflections	Δρmax = 0.14 e Å−3
112 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXTL'(Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0108 (8)

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	0.02008 (12)	0.12376 (4)	0.3335 (3)	0.0530 (5)
N1	−0.08464 (14)	0.07777 (6)	0.2532 (4)	0.0530 (6)
H1A	−0.1185	0.0952	0.1991	0.064*
H1B	−0.1013	0.0530	0.2556	0.064*
N2	0.15555 (13)	0.04420 (5)	0.1786 (2)	0.0364 (5)
N3	0.12698 (13)	0.00771 (5)	0.1195 (3)	0.0413 (5)
C1	−0.00707 (15)	0.08880 (6)	0.3326 (3)	0.0380 (5)
C2	0.04624 (16)	0.05620 (6)	0.4265 (3)	0.0435 (6)
H2A	0.0163	0.0307	0.4032	0.052*
H2B	0.0441	0.0609	0.5551	0.052*
C3	0.14666 (15)	0.05349 (7)	0.3680 (3)	0.0391 (5)
H3B	0.1771	0.0788	0.3924	0.047*
H3A	0.1775	0.0329	0.4379	0.047*
C4	0.2226 (2)	0.10885 (7)	0.0702 (5)	0.0622 (8)
H4B	0.2746	0.1082	0.1504	0.093*
H4C	0.1747	0.1253	0.1210	0.093*
H4A	0.2414	0.1198	−0.0434	0.093*
C5	0.18687 (15)	0.06742 (6)	0.0435 (3)	0.0422 (5)
C6	0.17798 (19)	0.04516 (8)	−0.1109 (4)	0.0505 (6)
H6A	0.1938	0.0529	−0.2270	0.061*
C7	0.14038 (16)	0.00856 (7)	−0.0582 (3)	0.0438 (6)
C8	0.1147 (2)	−0.02660 (9)	−0.1705 (5)	0.0628 (8)
H8A	0.1465	−0.0499	−0.1274	0.094*
H8B	0.1319	−0.0217	−0.2932	0.094*
H8C	0.0491	−0.0309	−0.1634	0.094*

	U11	U22	U33	U12	U13	U23
O1	0.0548 (10)	0.0323 (7)	0.0719 (13)	−0.0018 (6)	−0.0196 (10)	−0.0002 (8)
N1	0.0488 (10)	0.0381 (9)	0.0720 (16)	−0.0038 (8)	−0.0163 (12)	0.0039 (11)
N2	0.0386 (10)	0.0338 (10)	0.0369 (10)	0.0008 (7)	−0.0009 (9)	−0.0020 (8)
N3	0.0410 (10)	0.0342 (9)	0.0486 (12)	0.0007 (7)	−0.0011 (10)	−0.0057 (8)
C1	0.0391 (11)	0.0335 (9)	0.0415 (12)	0.0025 (8)	0.0025 (10)	−0.0037 (9)
C2	0.0473 (13)	0.0385 (11)	0.0447 (13)	0.0024 (9)	0.0045 (11)	0.0049 (10)
C3	0.0419 (12)	0.0367 (10)	0.0387 (12)	0.0061 (9)	−0.0027 (11)	−0.0005 (9)
C4	0.0787 (19)	0.0442 (13)	0.0636 (18)	−0.0134 (12)	0.0057 (17)	0.0057 (13)
C5	0.0425 (11)	0.0419 (10)	0.0422 (13)	−0.0005 (9)	0.0004 (12)	0.0018 (10)
C6	0.0521 (14)	0.0604 (16)	0.0390 (12)	−0.0001 (11)	0.0008 (12)	0.0009 (11)
C7	0.0365 (11)	0.0509 (14)	0.0441 (13)	0.0051 (9)	−0.0047 (11)	−0.0113 (11)
C8	0.0568 (15)	0.0671 (16)	0.0645 (19)	0.0018 (12)	−0.0065 (15)	−0.0243 (15)

O1—C1	1.232 (2)	C3—H3A	0.9700
N1—C1	1.320 (3)	C4—C5	1.490 (3)
N1—H1A	0.8598	C4—H4B	0.9600
N1—H1B	0.8603	C4—H4C	0.9600
N2—C5	1.347 (3)	C4—H4A	0.9600
N2—N3	1.359 (3)	C5—C6	1.373 (4)
N2—C3	1.448 (3)	C6—C7	1.394 (4)
N3—C7	1.335 (3)	C6—H6A	0.9300
C1—C2	1.505 (3)	C7—C8	1.488 (4)
C2—C3	1.518 (3)	C8—H8A	0.9600
C2—H2A	0.9700	C8—H8B	0.9600
C2—H2B	0.9700	C8—H8C	0.9600
C3—H3B	0.9700
C1—N1—H1A	120.2	C5—C4—H4B	109.5
C1—N1—H1B	119.8	C5—C4—H4C	109.5
H1A—N1—H1B	120.0	H4B—C4—H4C	109.5
C5—N2—N3	112.13 (18)	C5—C4—H4A	109.5
C5—N2—C3	129.18 (18)	H4B—C4—H4A	109.5
N3—N2—C3	118.66 (18)	H4C—C4—H4A	109.5
C7—N3—N2	104.88 (19)	N2—C5—C6	106.28 (19)
O1—C1—N1	122.5 (2)	N2—C5—C4	123.4 (2)
O1—C1—C2	121.3 (2)	C6—C5—C4	130.3 (2)
N1—C1—C2	116.14 (18)	C5—C6—C7	106.0 (2)
C1—C2—C3	113.56 (19)	C5—C6—H6A	127.0
C1—C2—H2A	108.9	C7—C6—H6A	127.0
C3—C2—H2A	108.9	N3—C7—C6	110.7 (2)
C1—C2—H2B	108.9	N3—C7—C8	120.2 (2)
C3—C2—H2B	108.9	C6—C7—C8	129.1 (3)
H2A—C2—H2B	107.7	C7—C8—H8A	109.5
N2—C3—C2	112.11 (19)	C7—C8—H8B	109.5
N2—C3—H3B	109.2	H8A—C8—H8B	109.5
C2—C3—H3B	109.2	C7—C8—H8C	109.5
N2—C3—H3A	109.2	H8A—C8—H8C	109.5
C2—C3—H3A	109.2	H8B—C8—H8C	109.5
H3B—C3—H3A	107.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.10	2.936 (3)	164
N1—H1B···N3ii	0.86	2.30	3.084 (3)	152
C3—H3B···O1iii	0.97	2.52	3.413 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.10	2.936 (3)	164
N1—H1B⋯N3ii	0.86	2.30	3.084 (3)	152
C3—H3B⋯O1iii	0.97	2.52	3.413 (3)	154

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