3-[3-(2-Pyrid-yl)-1H-pyrazol-1-yl]propan-amide.

In the title compound, C(11)H(12)N(4)O, the pyrazole and pyridine rings are nearly coplanar [dihedral angle = 1.87 (5)°]. Adjacent mol-ecules are linked by N-H⋯N and N-H⋯O hydrogen bonds into a linear chain running along the c axis.

Related literature

For the chemistry of 3-(2-pyrid­yl)pyrazoles, see: Ruben et al. (2004 ▶); Steel (2005 ▶).

Experimental

Crystal data

C11H12N4O

M = 216.25

Triclinic,

a = 7.7446 (15) Å

b = 8.3517 (17) Å

c = 8.4804 (17) Å

α = 97.99 (3)°

β = 98.95 (3)°

γ = 90.40 (3)°

V = 536.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.58 × 0.55 × 0.27 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.947, T max = 0.972

5019 measured reflections

2410 independent reflections

1937 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.139

S = 1.12

2410 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.28 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/S1600536809019060/ng2581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019060/ng2581Isup2.hkl

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

C11H12N4O	Z = 2
Mr = 216.25	F(000) = 228
Triclinic, P1	Dx = 1.339 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7446 (15) Å	Cell parameters from 5019 reflections
b = 8.3517 (17) Å	θ = 3.2–27.4°
c = 8.4804 (17) Å	µ = 0.09 mm−1
α = 97.99 (3)°	T = 293 K
β = 98.95 (3)°	Block, colorless
γ = 90.40 (3)°	0.58 × 0.55 × 0.27 mm
V = 536.4 (2) Å3

Rigaku R-AXIS RAPID diffractometer	2410 independent reflections
Radiation source: fine-focus sealed tube	1937 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 0 pixels mm-1	θmax = 27.4°, θmin = 3.2°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.947, Tmax = 0.972	l = −10→10
5019 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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0807P)2 + 0.0265P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2410 reflections	Δρmax = 0.37 e Å−3
146 parameters	Δρmin = −0.28 e Å−3
0 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: 0.038 (11)

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
N1	0.41230 (16)	0.30020 (14)	0.39463 (14)	0.0502 (3)
H1A	0.5037	0.3623	0.4058	0.060*
H1B	0.4039	0.2110	0.3293	0.060*
O1	0.28772 (12)	0.46829 (11)	0.57395 (12)	0.0495 (3)
C1	0.28366 (17)	0.34222 (15)	0.47849 (14)	0.0391 (3)
C2	0.13022 (19)	0.22241 (18)	0.44677 (16)	0.0509 (4)
H2A	0.0683	0.2257	0.3387	0.061*
H2B	0.1748	0.1145	0.4503	0.061*
C3	0.00195 (18)	0.25207 (18)	0.56416 (17)	0.0477 (4)
H3A	−0.0373	0.3623	0.5664	0.057*
H3B	−0.0994	0.1801	0.5266	0.057*
N2	0.07610 (14)	0.22676 (13)	0.72718 (13)	0.0403 (3)
C4	0.0879 (2)	0.33312 (17)	0.86282 (18)	0.0500 (4)
H4A	0.0518	0.4395	0.8703	0.060*
C5	0.1622 (2)	0.25694 (17)	0.98736 (17)	0.0496 (4)
H5A	0.1874	0.2996	1.0959	0.060*
C6	0.19232 (15)	0.09985 (15)	0.91577 (15)	0.0367 (3)
N3	0.13956 (14)	0.08220 (13)	0.75618 (13)	0.0401 (3)
C7	0.26942 (15)	−0.03550 (14)	0.99317 (15)	0.0368 (3)
C8	0.28816 (18)	−0.18581 (16)	0.90392 (18)	0.0457 (3)
H8A	0.2547	−0.2021	0.7926	0.055*
C9	0.3569 (2)	−0.30988 (17)	0.9829 (2)	0.0555 (4)
H9A	0.3706	−0.4110	0.9253	0.067*
C10	0.4054 (2)	−0.28298 (19)	1.1479 (2)	0.0576 (4)
H10A	0.4498	−0.3655	1.2041	0.069*
C11	0.3862 (2)	−0.13031 (19)	1.22693 (19)	0.0538 (4)
H11A	0.4210	−0.1116	1.3381	0.065*
N4	0.32045 (15)	−0.00708 (14)	1.15354 (14)	0.0451 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0535 (7)	0.0437 (6)	0.0500 (7)	−0.0114 (5)	0.0099 (5)	−0.0069 (5)
O1	0.0528 (6)	0.0395 (5)	0.0531 (6)	−0.0070 (4)	0.0085 (5)	−0.0038 (4)
C1	0.0461 (7)	0.0361 (6)	0.0327 (6)	−0.0044 (5)	−0.0025 (5)	0.0070 (5)
C2	0.0590 (9)	0.0539 (8)	0.0366 (7)	−0.0193 (7)	0.0031 (6)	0.0012 (6)
C3	0.0437 (7)	0.0515 (8)	0.0466 (8)	−0.0067 (6)	−0.0011 (6)	0.0121 (6)
N2	0.0428 (6)	0.0378 (6)	0.0409 (6)	0.0012 (4)	0.0078 (4)	0.0057 (4)
C4	0.0662 (9)	0.0374 (7)	0.0486 (8)	0.0102 (6)	0.0171 (7)	0.0040 (6)
C5	0.0715 (9)	0.0410 (7)	0.0364 (7)	0.0097 (6)	0.0124 (6)	0.0007 (5)
C6	0.0361 (6)	0.0354 (6)	0.0389 (7)	−0.0020 (5)	0.0092 (5)	0.0028 (5)
N3	0.0408 (6)	0.0356 (5)	0.0421 (6)	−0.0008 (4)	0.0037 (4)	0.0019 (4)
C7	0.0326 (6)	0.0358 (6)	0.0418 (7)	−0.0022 (5)	0.0071 (5)	0.0031 (5)
C8	0.0439 (7)	0.0412 (7)	0.0479 (8)	0.0025 (5)	0.0031 (6)	−0.0025 (6)
C9	0.0539 (8)	0.0384 (7)	0.0704 (10)	0.0086 (6)	0.0045 (7)	−0.0001 (7)
C10	0.0580 (9)	0.0467 (8)	0.0698 (11)	0.0122 (7)	0.0072 (7)	0.0175 (7)
C11	0.0603 (9)	0.0545 (8)	0.0469 (8)	0.0079 (7)	0.0048 (6)	0.0120 (7)
N4	0.0515 (7)	0.0417 (6)	0.0417 (6)	0.0033 (5)	0.0072 (5)	0.0041 (5)

N1—C1	1.3332 (18)	C5—C6	1.4040 (18)
N1—H1A	0.8600	C5—H5A	0.9300
N1—H1B	0.8600	C6—N3	1.3386 (16)
O1—C1	1.2328 (16)	C6—C7	1.4693 (18)
C1—C2	1.5150 (18)	C7—N4	1.3431 (18)
C2—C3	1.511 (2)	C7—C8	1.3938 (19)
C2—H2A	0.9700	C8—C9	1.377 (2)
C2—H2B	0.9700	C8—H8A	0.9300
C3—N2	1.4566 (18)	C9—C10	1.378 (2)
C3—H3A	0.9700	C9—H9A	0.9300
C3—H3B	0.9700	C10—C11	1.376 (2)
N2—C4	1.3427 (19)	C10—H10A	0.9300
N2—N3	1.3464 (16)	C11—N4	1.3389 (19)
C4—C5	1.362 (2)	C11—H11A	0.9300
C4—H4A	0.9300
C1—N1—H1A	120.0	C4—C5—C6	104.82 (13)
C1—N1—H1B	120.0	C4—C5—H5A	127.6
H1A—N1—H1B	120.0	C6—C5—H5A	127.6
O1—C1—N1	123.19 (12)	N3—C6—C5	110.81 (12)
O1—C1—C2	122.26 (12)	N3—C6—C7	120.56 (11)
N1—C1—C2	114.55 (11)	C5—C6—C7	128.63 (12)
C3—C2—C1	114.53 (11)	C6—N3—N2	104.84 (10)
C3—C2—H2A	108.6	N4—C7—C8	121.89 (13)
C1—C2—H2A	108.6	N4—C7—C6	116.74 (11)
C3—C2—H2B	108.6	C8—C7—C6	121.38 (12)
C1—C2—H2B	108.6	C9—C8—C7	119.08 (14)
H2A—C2—H2B	107.6	C9—C8—H8A	120.5
N2—C3—C2	112.93 (12)	C7—C8—H8A	120.5
N2—C3—H3A	109.0	C8—C9—C10	119.41 (14)
C2—C3—H3A	109.0	C8—C9—H9A	120.3
N2—C3—H3B	109.0	C10—C9—H9A	120.3
C2—C3—H3B	109.0	C11—C10—C9	118.01 (15)
H3A—C3—H3B	107.8	C11—C10—H10A	121.0
C4—N2—N3	111.95 (11)	C9—C10—H10A	121.0
C4—N2—C3	127.56 (12)	N4—C11—C10	123.96 (15)
N3—N2—C3	120.47 (11)	N4—C11—H11A	118.0
N2—C4—C5	107.59 (13)	C10—C11—H11A	118.0
N2—C4—H4A	126.2	C11—N4—C7	117.61 (12)
C5—C4—H4A	126.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.11	2.968 (2)	175
N1—H1B···N4ii	0.86	2.21	3.055 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.11	2.968 (2)	175
N1—H1B⋯N4ii	0.86	2.21	3.055 (2)	167

Symmetry codes: (i) ; (ii) .