1-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbon-yl]-5-methyl-indolizine-3-carbo-nitrile.

In the title mol-ecule, C16H14N4O, the indolizine ring system is essentially planar, with a maximum deviation of 0.013 (3) Å, and forms a dihedral angle of 7.52 (12)° with the pyrazole ring. In the crystal, weak C-H⋯O hydrogen bonds and π-π stacking inter-actions, with a centroid-centroid distance of 3.6378 (16) Å, link mol-ecules along [001].

Related literature

For biological applications of indolizines and pyrazoles, see: Tukulula et al. (2010 ▶); James et al. (2008 ▶); Teklu et al. (2005 ▶); McDonald et al. (2006 ▶); Jagerovic et al. (2002 ▶). For background and the synthesis of related hetrocycles, see: Gu et al. (2011 ▶); Shen et al. (2006 ▶, 2008 ▶); Wang, et al. (2000 ▶).

Experimental

Crystal data

C16H14N4O

M = 278.31

Monoclinic,

a = 8.5911 (18) Å

b = 23.3760 (15) Å

c = 7.5816 (12) Å

β = 114.775 (3)°

V = 1382.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.974, T max = 0.983

7822 measured reflections

2361 independent reflections

1728 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 1.05

2361 reflections

194 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812046727/lh5554sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046727/lh5554Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046727/lh5554Isup3.cml

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

C16H14N4O	F(000) = 584
Mr = 278.31	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1864 reflections
a = 8.5911 (18) Å	θ = 2.1–23.1°
b = 23.3760 (15) Å	µ = 0.09 mm−1
c = 7.5816 (12) Å	T = 291 K
β = 114.775 (3)°	Block, colorless
V = 1382.4 (4) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	2361 independent reflections
Radiation source: sealed tube	1728 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.974, Tmax = 0.983	k = −27→27
7822 measured reflections	l = −8→7

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.2279P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2361 reflections	Δρmax = 0.19 e Å−3
194 parameters	Δρmin = −0.15 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: 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
C1	0.4078 (3)	0.16105 (9)	0.6276 (3)	0.0539 (6)
C2	0.5673 (3)	0.16955 (11)	0.7688 (3)	0.0674 (7)
H2	0.6342	0.1380	0.8292	0.081*
C3	0.6350 (3)	0.22472 (11)	0.8269 (4)	0.0706 (7)
H3	0.7458	0.2291	0.9227	0.085*
C4	0.5393 (3)	0.27142 (10)	0.7437 (3)	0.0610 (6)
H4	0.5835	0.3079	0.7834	0.073*
C5	0.3740 (3)	0.26454 (9)	0.5980 (3)	0.0494 (5)
C6	0.2428 (2)	0.30329 (9)	0.4823 (3)	0.0473 (5)
C7	0.1052 (3)	0.27046 (9)	0.3576 (3)	0.0502 (5)
H7	0.0023	0.2849	0.2655	0.060*
C8	0.1454 (2)	0.21350 (7)	0.3920 (3)	0.0495 (5)
C9	0.0408 (3)	0.16786 (8)	0.2894 (3)	0.0572 (6)
C10	0.3329 (3)	0.10310 (10)	0.5630 (4)	0.0698 (7)
H10A	0.4101	0.0746	0.6440	0.105*
H10B	0.3150	0.0971	0.4305	0.105*
H10C	0.2253	0.1003	0.5727	0.105*
C11	0.2680 (3)	0.36492 (10)	0.5125 (3)	0.0553 (6)
C12	0.1506 (3)	0.46295 (9)	0.3983 (3)	0.0514 (5)
C13	0.0074 (3)	0.48077 (9)	0.2476 (3)	0.0565 (6)
H13	−0.0256	0.5186	0.2140	0.068*
C14	−0.0831 (3)	0.43187 (9)	0.1502 (3)	0.0524 (5)
C15	−0.2500 (3)	0.42892 (10)	−0.0234 (4)	0.0673 (7)
H15A	−0.2309	0.4329	−0.1389	0.101*
H15B	−0.3232	0.4592	−0.0178	0.101*
H15C	−0.3035	0.3927	−0.0256	0.101*
C16	0.2889 (3)	0.49760 (11)	0.5473 (4)	0.0703 (7)
H16A	0.2630	0.5375	0.5222	0.105*
H16B	0.3963	0.4894	0.5418	0.105*
H16C	0.2966	0.4882	0.6740	0.105*
N1	0.3117 (2)	0.20945 (7)	0.5412 (2)	0.0481 (5)
N2	−0.0540 (3)	0.13371 (9)	0.1932 (3)	0.0792 (7)
N3	0.1439 (2)	0.40334 (7)	0.3880 (3)	0.0505 (5)
N4	−0.0015 (2)	0.38486 (7)	0.2341 (3)	0.0543 (5)
O1	0.3936 (2)	0.38496 (7)	0.6446 (3)	0.0837 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0572 (14)	0.0536 (13)	0.0514 (13)	0.0122 (10)	0.0232 (12)	0.0077 (10)
C2	0.0593 (15)	0.0719 (17)	0.0605 (16)	0.0190 (12)	0.0147 (14)	0.0098 (12)
C3	0.0499 (14)	0.0874 (19)	0.0578 (16)	0.0108 (13)	0.0061 (12)	0.0002 (13)
C4	0.0555 (14)	0.0631 (14)	0.0525 (14)	0.0036 (11)	0.0108 (12)	−0.0049 (11)
C5	0.0492 (13)	0.0542 (13)	0.0434 (13)	0.0025 (10)	0.0179 (11)	−0.0012 (9)
C6	0.0466 (12)	0.0495 (12)	0.0415 (12)	0.0015 (9)	0.0141 (10)	−0.0008 (9)
C7	0.0452 (12)	0.0535 (13)	0.0452 (12)	0.0017 (9)	0.0125 (10)	0.0023 (10)
C8	0.0473 (12)	0.0498 (13)	0.0480 (13)	0.0019 (9)	0.0165 (11)	0.0023 (9)
C9	0.0535 (14)	0.0513 (13)	0.0578 (15)	−0.0016 (11)	0.0145 (12)	0.0037 (11)
C10	0.0733 (16)	0.0571 (15)	0.0756 (18)	0.0125 (12)	0.0280 (14)	0.0122 (12)
C11	0.0493 (13)	0.0569 (14)	0.0483 (13)	−0.0009 (10)	0.0092 (12)	−0.0052 (10)
C12	0.0494 (13)	0.0480 (12)	0.0565 (13)	−0.0065 (10)	0.0220 (11)	−0.0069 (10)
C13	0.0534 (13)	0.0433 (12)	0.0677 (15)	0.0006 (10)	0.0205 (12)	0.0015 (10)
C14	0.0503 (12)	0.0483 (12)	0.0548 (14)	0.0005 (10)	0.0183 (11)	0.0023 (10)
C15	0.0541 (14)	0.0627 (15)	0.0688 (16)	0.0000 (11)	0.0096 (13)	0.0040 (12)
C16	0.0640 (15)	0.0585 (15)	0.0795 (18)	−0.0122 (11)	0.0213 (14)	−0.0131 (12)
N1	0.0475 (10)	0.0517 (10)	0.0441 (11)	0.0068 (8)	0.0181 (9)	0.0030 (8)
N2	0.0789 (15)	0.0564 (13)	0.0822 (16)	−0.0097 (11)	0.0141 (13)	0.0027 (11)
N3	0.0496 (10)	0.0445 (10)	0.0497 (11)	−0.0015 (8)	0.0134 (9)	−0.0016 (8)
N4	0.0490 (10)	0.0487 (10)	0.0510 (11)	−0.0034 (8)	0.0071 (9)	−0.0007 (8)
O1	0.0668 (11)	0.0636 (10)	0.0771 (12)	−0.0006 (9)	−0.0126 (10)	−0.0156 (9)

C1—C2	1.354 (3)	C10—H10B	0.9600
C1—N1	1.392 (3)	C10—H10C	0.9600
C1—C10	1.492 (3)	C11—O1	1.217 (3)
C2—C3	1.407 (3)	C11—N3	1.411 (3)
C2—H2	0.9300	C12—C13	1.347 (3)
C3—C4	1.353 (3)	C12—N3	1.395 (3)
C3—H3	0.9300	C12—C16	1.490 (3)
C4—C5	1.396 (3)	C13—C14	1.405 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—N1	1.392 (3)	C14—N4	1.315 (3)
C5—C6	1.426 (3)	C14—C15	1.487 (3)
C6—C7	1.394 (3)	C15—H15A	0.9600
C6—C11	1.460 (3)	C15—H15B	0.9600
C7—C8	1.373 (3)	C15—H15C	0.9600
C7—H7	0.9300	C16—H16A	0.9600
C8—C9	1.4017 (10)	C16—H16B	0.9600
C8—N1	1.405 (3)	C16—H16C	0.9600
C9—N2	1.156 (2)	N3—N4	1.374 (2)
C10—H10A	0.9600
C2—C1—N1	117.2 (2)	O1—C11—N3	117.8 (2)
C2—C1—C10	123.2 (2)	O1—C11—C6	122.1 (2)
N1—C1—C10	119.6 (2)	N3—C11—C6	120.15 (19)
C1—C2—C3	122.0 (2)	C13—C12—N3	105.07 (18)
C1—C2—H2	119.0	C13—C12—C16	129.0 (2)
C3—C2—H2	119.0	N3—C12—C16	125.9 (2)
C4—C3—C2	120.2 (2)	C12—C13—C14	107.56 (19)
C4—C3—H3	119.9	C12—C13—H13	126.2
C2—C3—H3	119.9	C14—C13—H13	126.2
C3—C4—C5	119.6 (2)	N4—C14—C13	111.09 (19)
C3—C4—H4	120.2	N4—C14—C15	120.68 (19)
C5—C4—H4	120.2	C13—C14—C15	128.2 (2)
N1—C5—C4	118.9 (2)	C14—C15—H15A	109.5
N1—C5—C6	107.16 (18)	C14—C15—H15B	109.5
C4—C5—C6	133.9 (2)	H15A—C15—H15B	109.5
C7—C6—C5	107.14 (19)	C14—C15—H15C	109.5
C7—C6—C11	132.6 (2)	H15A—C15—H15C	109.5
C5—C6—C11	120.22 (19)	H15B—C15—H15C	109.5
C8—C7—C6	109.30 (19)	C12—C16—H16A	109.5
C8—C7—H7	125.3	C12—C16—H16B	109.5
C6—C7—H7	125.3	H16A—C16—H16B	109.5
C7—C8—C9	125.51 (19)	C12—C16—H16C	109.5
C7—C8—N1	107.97 (16)	H16A—C16—H16C	109.5
C9—C8—N1	126.47 (18)	H16B—C16—H16C	109.5
N2—C9—C8	174.1 (2)	C1—N1—C5	122.08 (18)
C1—C10—H10A	109.5	C1—N1—C8	129.49 (17)
C1—C10—H10B	109.5	C5—N1—C8	108.43 (16)
H10A—C10—H10B	109.5	N4—N3—C12	111.28 (17)
C1—C10—H10C	109.5	N4—N3—C11	122.09 (16)
H10A—C10—H10C	109.5	C12—N3—C11	126.62 (18)
H10B—C10—H10C	109.5	C14—N4—N3	105.00 (16)
N1—C1—C2—C3	−0.1 (3)	C10—C1—N1—C5	178.91 (19)
C10—C1—C2—C3	179.9 (2)	C2—C1—N1—C8	179.34 (19)
C1—C2—C3—C4	1.1 (4)	C10—C1—N1—C8	−0.7 (3)
C2—C3—C4—C5	−0.9 (4)	C4—C5—N1—C1	1.2 (3)
C3—C4—C5—N1	−0.2 (3)	C6—C5—N1—C1	−179.24 (16)
C3—C4—C5—C6	−179.6 (2)	C4—C5—N1—C8	−179.07 (17)
N1—C5—C6—C7	−0.5 (2)	C6—C5—N1—C8	0.5 (2)
C4—C5—C6—C7	178.9 (2)	C7—C8—N1—C1	179.42 (18)
N1—C5—C6—C11	178.04 (17)	C9—C8—N1—C1	−3.2 (3)
C4—C5—C6—C11	−2.5 (3)	C7—C8—N1—C5	−0.2 (2)
C5—C6—C7—C8	0.4 (2)	C9—C8—N1—C5	177.15 (19)
C11—C6—C7—C8	−177.9 (2)	C13—C12—N3—N4	−0.3 (2)
C6—C7—C8—C9	−177.50 (19)	C16—C12—N3—N4	179.45 (18)
C6—C7—C8—N1	−0.1 (2)	C13—C12—N3—C11	178.35 (18)
C7—C6—C11—O1	172.3 (2)	C16—C12—N3—C11	−1.9 (3)
C5—C6—C11—O1	−5.8 (3)	O1—C11—N3—N4	179.5 (2)
C7—C6—C11—N3	−6.9 (3)	C6—C11—N3—N4	−1.2 (3)
C5—C6—C11—N3	175.01 (17)	O1—C11—N3—C12	1.0 (3)
N3—C12—C13—C14	0.3 (2)	C6—C11—N3—C12	−179.75 (18)
C16—C12—C13—C14	−179.5 (2)	C13—C14—N4—N3	0.0 (2)
C12—C13—C14—N4	−0.2 (3)	C15—C14—N4—N3	−179.36 (18)
C12—C13—C14—C15	179.1 (2)	C12—N3—N4—C14	0.2 (2)
C2—C1—N1—C5	−1.0 (3)	C11—N3—N4—C14	−178.54 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1i	0.96	2.56	3.435 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1i	0.96	2.56	3.435 (4)	151

Symmetry code: (i) .