1-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbon­yl]-5-methyl­indolizine-3-carbo­nitrile

Gu, W.-J.; Xie, W.-L.; Wang, T.-T.

doi:10.1107/S1600536812046727

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3399

doi:10.1107/S1600536812046727

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1-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbonyl]-5-methylindolizine-3-carbonitrile

Wei-Jin Gu,^a,^b ^* Wen-Li Xie ^a and Ting-Ting Wang ^a

^aDepartment of Applied Chemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China, and ^bKey Laboratory of Applied Photochemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China
^*Correspondence e-mail: guweijin2010@163.com

(Received 5 November 2012; accepted 13 November 2012; online 24 November 2012)

In the title molecule, 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 interactions, with a centroid–centroid distance of 3.6378 (16) Å, link molecules 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_r = 278.31
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.135
S = 1.05
2361 reflections
194 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812046727/lh5554sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812046727/lh5554Isup3.cml

checkCIF report

Comment top

Indolizines and pyrazoles are important classes of bio-active drug targets in the pharmaceutical industry, as they are the core structure of numerous biologically active compounds (Tukulula et al., 2010; James et al., 2008; Teklu et al., 2005; McDonald et al., 2006; Jagerovic et al., 2002). In our continuing studies on the synthesis and properties of heterocycles (Gu et al., 2011; Shen et al., 2008; Shen et al., 2006; Wang, et al., 2000) we have prepared (Fig. 1) and determined the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 2. The indolizine ring system is essentially planar with a maximum deviation for atom C3 of 0.013 (3)Å. The dihedral angle formed by the indolizine ring system and the pyrazole ring is 7.52 (12)°. In the crystal, weak C—H···O hydrogen bonds and π–π stacking interactions, with Cg1···Cg2ⁱ = 3.6378 (16)Å, link molecules along [001] (Fig. 3). Cg1 and Cg2 are the centroids of the N1/C5-C8 and N1/C1-C5 rings (symmetry code (i): x, 1/2-y, -1/2+z).

Related literature top

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 top

Methyl-3-cyano-5-methylindolizine-1-carboxylate was prepared through 1,3-dipolar cycloaddition according to a procedure described in the literature (Wang, et al., 2000). A suspension of N-cyano-2-methylpyridinium bromide (C₅H₄N⁺CH₃CN.Br^-) (10 mmol), ethyl acrylate (40 mmol), Et₃N (20 ml) and CrO₃ (20 mmol) in DMF (40 ml) was stirred at 363K for 4 h (monitored by TLC). The mixture was cooled to room temperature and poured into 5% aqueous HCl (150 mL). The brown powder was collected by filtration and washed with ethanol (25 mL). After drying the solid was collected 1.28 g (60%).

Methyl-3-cyano-5-methylindolizine-1-carboxylate (5 mmol) was dissolved in 6 ml of ethanol and 20 ml 80% N₂H₄.H₂O (30 mmol) was added dropwise. The solution was refluxed for 6 h and cooled to yield the product, 0.87 g (81%) as 3-cyano-5-methylindolizine-1-carbohydrazide.

3-cyano-5-methylindolizine-1-carbohydrazide (1 mmol) was dissolved in 2 ml acetic acid, then acetylacetone (2 mmol, dissolved in 2ml ethanol) was added. After stirring for 2 h, the mixture was purified by chromatography [silica gel, 20% ethyl acetate in petroleum ether (60 C90)] to yield colorless block crystals of the title compound, 0.22 g (79%). 1H-NMR (CDCl₃, 400 MHz): 2.33 (s, 3H, –CH3), 2.65 (s, 3H, –CH3), 3.06 (s, 3H, –CH3), 6.06 (s, 1H, pyrazole =CH), 6.80 (d, 1H, indolizine =CH), 7.33 (t, 1H, indolizine =CH), 8.52 (d, 1H, indolizine =CH), 8.59 (s, 1H, indolizine =CH).

Computing details top

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

Figures top

	Fig. 1. The reaction scheme.
	Fig. 2. The molecular structure of title compound. Displacement ellipsoids at the 50% probability level.
	Fig. 3. Part of the crystal structure with weak hydrogen bonds shown as dashed lines.

1-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbonyl]-5-methylindolizine- 3-carbonitrile top

Crystal data top

C₁₆H₁₄N₄O	F(000) = 584
M_r = 278.31	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0667P)² + 0.2279P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2361 reflections	Δρ_max = 0.19 e Å⁻³
194 parameters	Δρ_min = −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

Crystal data top

C₁₆H₁₄N₄O	V = 1382.4 (4) Å³
M_r = 278.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5911 (18) Å	µ = 0.09 mm⁻¹
b = 23.3760 (15) Å	T = 291 K
c = 7.5816 (12) Å	0.30 × 0.25 × 0.20 mm
β = 114.775 (3)°

Data collection top

Bruker SMART APEX diffractometer	2361 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1728 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.037
7822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.135	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
2361 reflections	Δρ_min = −0.15 e Å⁻³
194 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₄O
M_r	278.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	8.5911 (18), 23.3760 (15), 7.5816 (12)
β (°)	114.775 (3)
V (Å³)	1382.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	7822, 2361, 1728
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.135, 1.05
No. of reflections	2361
No. of parameters	194
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2.

Acknowledgements

We thank the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) for financial support.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gu, W.-J., Zhuang, J., Jiang, Y.-L. & Wang, B.-X. (2011). Acta Cryst. E67, o123. Web of Science CrossRef IUCr Journals Google Scholar
Jagerovic, N., Cano, C., Elguero, J. & Goya, P. (2002). Bioorg. Med. Chem. 10, 817–827. Web of Science CrossRef PubMed CAS Google Scholar
James, D. A., Koya, K., Li, H., Liang, G. Q., Xia, Z. Q., Ying, W. W., Wu, Y. M. & Sun, L. J. (2008). Bioorg. Med. Chem. Lett. 18, 1784–1787. Web of Science CrossRef PubMed CAS Google Scholar
McDonald, E., Workman, P. & Jones, K. (2006). Curr. Top. Med. Chem. 6, 1091–1107. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, Y.-M., Wang, B.-X., Feng, Y.-Y., Shen, Z.-Y., Shen, J., Li, C. & Hu, H.-W. (2006). Chem. J. Chin. Univ. 27, 651–653. CAS Google Scholar
Shen, Z.-Y., Wang, B.-X., Shen, J. & Hu, H.-W. (2008). Chem. J. Chin. Univ. 29, 916–918. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127–3139. Web of Science CrossRef PubMed CAS Google Scholar
Tukulula, M., Klein, R. & Kaye, P. T. (2010). Synth. Commun. 40, 2018–2028. Web of Science CrossRef CAS Google Scholar
Wang, B.-X., Hu, J.-X., Zhang, X.-C., Hu, Y.-F. & Hu, H.-W. (2000). J. Heterocycl. Chem. 37, 1533-1537. CrossRef CAS Google Scholar

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Volume 68| Part 12| December 2012| Page o3399

doi:10.1107/S1600536812046727

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[(3,5-Di­methyl-1H-pyrazol-1-yl)carbon­yl]-5-methyl­indolizine-3-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbonyl]-5-methylindolizine-3-carbonitrile