Ethyl 6-amino-5-cyano-4-isopropyl-2-methyl-4H-pyran-3-carboxyl-ate.

In the title compound, C(13)H(18)N(2)O(3), the two H atoms of the NH(2) group are engaged in hydrogen bonding with the N atom of the cyano group and with one O atom of the ethoxy-carbonyl group, building a chain parallel to the [100] direction. The N-H⋯N hydrogen bonds assemble the mol-ecules around inversion centres, forming dimers with an R(2) (2)(12) graph-set motif.

Related literature

For general background, see: Messaâd et al. (2005 ▶, 2006 ▶); Mohr et al. (1975 ▶); Ohira & Yatagai (1993 ▶); Tandon et al. (1991 ▶); Wang et al. (1996 ▶); Zamocka et al. (1992 ▶); Bloxham et al. (1994 ▶); Elagamey et al. (1993 ▶); Khafagy et al. (2002 ▶). For graph-set notation, see: Etter (1990 ▶); Bernstein et al. (1994 ▶).

Experimental

Crystal data

C13H18N2O3

M = 250.29

Triclinic,

a = 8.0856 (1) Å

b = 9.3193 (2) Å

c = 10.4563 (2) Å

α = 65.652 (1)°

β = 69.679 (1)°

γ = 76.105 (1)°

V = 668.80 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.44 × 0.36 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.959, T max = 0.982

17876 measured reflections

4664 independent reflections

3324 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.143

S = 1.05

4664 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804052X/dn2412sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804052X/dn2412Isup2.hkl

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

C13H18N2O3	Z = 2
Mr = 250.29	F(000) = 268
Triclinic, P1	Dx = 1.243 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0856 (1) Å	Cell parameters from 2132 reflections
b = 9.3193 (2) Å	θ = 2.3–21.2°
c = 10.4563 (2) Å	µ = 0.09 mm−1
α = 65.652 (1)°	T = 296 K
β = 69.679 (1)°	Prism, colourless
γ = 76.105 (1)°	0.44 × 0.36 × 0.18 mm
V = 668.80 (2) Å3

Bruker SMART CCD area-detector diffractometer	4664 independent reflections
Radiation source: sealed tube	3324 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 32.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
Tmin = 0.959, Tmax = 0.982	k = −13→12
17876 measured reflections	l = −15→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0801P)2 + 0.026P] where P = (Fo2 + 2Fc2)/3
4664 reflections	(Δ/σ)max = 0.009
167 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.36662 (8)	0.54982 (7)	0.29951 (8)	0.03977 (18)
O2	−0.23592 (10)	0.56365 (10)	0.34370 (11)	0.0559 (2)
O3	−0.12340 (9)	0.79434 (9)	0.22760 (9)	0.0463 (2)
N2	0.54618 (11)	0.33268 (10)	0.37642 (11)	0.0440 (2)
H2A	0.6161	0.3972	0.3631	0.053*
H2B	0.5773	0.2321	0.4080	0.053*
N3	0.29885 (15)	0.00436 (11)	0.48430 (13)	0.0583 (3)
C1	0.38924 (12)	0.38872 (11)	0.34801 (10)	0.0340 (2)
C2	0.26177 (12)	0.30627 (10)	0.36205 (10)	0.0341 (2)
C3	0.10119 (11)	0.39019 (10)	0.30733 (10)	0.03172 (19)
H3	−0.0020	0.3380	0.3801	0.038*
C4	0.07103 (11)	0.55961 (10)	0.29910 (10)	0.03243 (19)
C5	0.19954 (12)	0.63057 (10)	0.29517 (10)	0.0344 (2)
C6	−0.11029 (12)	0.63756 (12)	0.29492 (11)	0.0364 (2)
C7	−0.29880 (14)	0.87305 (14)	0.21657 (15)	0.0535 (3)
H7A	−0.3819	0.8524	0.3133	0.064*
H7B	−0.3409	0.8342	0.1618	0.064*
C8	−0.2844 (2)	1.04593 (17)	0.14025 (19)	0.0738 (4)
H8A	−0.2495	1.0843	0.1982	0.111*
H8B	−0.3973	1.1007	0.1264	0.111*
H8C	−0.1972	1.0644	0.0469	0.111*
C9	0.28332 (13)	0.13998 (11)	0.42860 (12)	0.0393 (2)
C10	0.19803 (15)	0.79274 (12)	0.28995 (14)	0.0471 (3)
H10A	0.0785	0.8439	0.3048	0.071*
H10B	0.2700	0.8531	0.1963	0.071*
H10C	0.2446	0.7859	0.3654	0.071*
C11	0.11157 (12)	0.38374 (12)	0.15880 (11)	0.0382 (2)
H11	0.0071	0.4499	0.1297	0.046*
C12	0.27420 (17)	0.45164 (17)	0.03829 (13)	0.0573 (3)
H12A	0.3795	0.3903	0.0639	0.086*
H12B	0.2728	0.5596	0.0266	0.086*
H12C	0.2730	0.4479	−0.0518	0.086*
C13	0.1026 (2)	0.21704 (15)	0.17254 (16)	0.0614 (3)
H13A	0.0852	0.2204	0.0850	0.092*
H13B	0.0054	0.1728	0.2548	0.092*
H13C	0.2116	0.1525	0.1865	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0361 (3)	0.0241 (3)	0.0613 (4)	−0.0051 (2)	−0.0227 (3)	−0.0092 (3)
O2	0.0355 (4)	0.0475 (5)	0.0925 (6)	−0.0084 (3)	−0.0162 (4)	−0.0320 (4)
O3	0.0353 (3)	0.0343 (4)	0.0665 (5)	0.0028 (3)	−0.0207 (3)	−0.0140 (3)
N2	0.0393 (4)	0.0292 (4)	0.0672 (6)	−0.0028 (3)	−0.0279 (4)	−0.0109 (4)
N3	0.0649 (6)	0.0298 (5)	0.0844 (8)	−0.0039 (4)	−0.0399 (6)	−0.0098 (5)
C1	0.0358 (4)	0.0255 (4)	0.0421 (5)	−0.0041 (3)	−0.0164 (4)	−0.0088 (3)
C2	0.0378 (4)	0.0246 (4)	0.0437 (5)	−0.0043 (3)	−0.0185 (4)	−0.0100 (3)
C3	0.0322 (4)	0.0248 (4)	0.0417 (4)	−0.0057 (3)	−0.0146 (3)	−0.0106 (3)
C4	0.0320 (4)	0.0264 (4)	0.0424 (5)	−0.0030 (3)	−0.0143 (3)	−0.0128 (3)
C5	0.0357 (4)	0.0258 (4)	0.0450 (5)	−0.0038 (3)	−0.0171 (4)	−0.0111 (3)
C6	0.0334 (4)	0.0343 (5)	0.0481 (5)	−0.0018 (3)	−0.0138 (4)	−0.0204 (4)
C7	0.0398 (5)	0.0505 (7)	0.0749 (8)	0.0106 (5)	−0.0261 (5)	−0.0276 (6)
C8	0.0675 (8)	0.0544 (8)	0.0838 (10)	0.0189 (6)	−0.0321 (7)	−0.0150 (7)
C9	0.0413 (5)	0.0289 (5)	0.0525 (5)	−0.0034 (4)	−0.0224 (4)	−0.0120 (4)
C10	0.0509 (5)	0.0294 (5)	0.0710 (7)	−0.0048 (4)	−0.0277 (5)	−0.0188 (5)
C11	0.0393 (5)	0.0369 (5)	0.0472 (5)	−0.0021 (4)	−0.0200 (4)	−0.0183 (4)
C12	0.0578 (7)	0.0678 (8)	0.0461 (6)	−0.0139 (6)	−0.0110 (5)	−0.0195 (6)
C13	0.0818 (9)	0.0518 (7)	0.0718 (8)	−0.0148 (6)	−0.0272 (7)	−0.0343 (6)

O1—C1	1.3599 (11)	C7—C8	1.4871 (18)
O1—C5	1.3855 (11)	C7—H7A	0.9700
O2—C6	1.2053 (11)	C7—H7B	0.9700
O3—C6	1.3308 (12)	C8—H8A	0.9600
O3—C7	1.4516 (12)	C8—H8B	0.9600
N2—C1	1.3367 (11)	C8—H8C	0.9600
N2—H2A	0.8600	C10—H10A	0.9600
N2—H2B	0.8600	C10—H10B	0.9600
N3—C9	1.1489 (13)	C10—H10C	0.9600
C1—C2	1.3625 (12)	C11—C13	1.5172 (15)
C2—C9	1.4077 (13)	C11—C12	1.5194 (15)
C2—C3	1.5113 (12)	C11—H11	0.9800
C3—C4	1.5091 (12)	C12—H12A	0.9600
C3—C11	1.5513 (13)	C12—H12B	0.9600
C3—H3	0.9800	C12—H12C	0.9600
C4—C5	1.3404 (11)	C13—H13A	0.9600
C4—C6	1.4785 (12)	C13—H13B	0.9600
C5—C10	1.4868 (13)	C13—H13C	0.9600
C1—O1—C5	119.76 (7)	C7—C8—H8A	109.5
C6—O3—C7	116.29 (8)	C7—C8—H8B	109.5
C1—N2—H2A	120.0	H8A—C8—H8B	109.5
C1—N2—H2B	120.0	C7—C8—H8C	109.5
H2A—N2—H2B	120.0	H8A—C8—H8C	109.5
N2—C1—O1	110.47 (7)	H8B—C8—H8C	109.5
N2—C1—C2	128.56 (8)	N3—C9—C2	179.11 (13)
O1—C1—C2	120.97 (8)	C5—C10—H10A	109.5
C1—C2—C9	118.33 (8)	C5—C10—H10B	109.5
C1—C2—C3	121.20 (8)	H10A—C10—H10B	109.5
C9—C2—C3	120.47 (7)	C5—C10—H10C	109.5
C4—C3—C2	109.19 (7)	H10A—C10—H10C	109.5
C4—C3—C11	110.66 (7)	H10B—C10—H10C	109.5
C2—C3—C11	114.29 (8)	C13—C11—C12	110.81 (10)
C4—C3—H3	107.5	C13—C11—C3	111.65 (9)
C2—C3—H3	107.5	C12—C11—C3	112.53 (8)
C11—C3—H3	107.5	C13—C11—H11	107.2
C5—C4—C6	124.13 (8)	C12—C11—H11	107.2
C5—C4—C3	121.99 (8)	C3—C11—H11	107.2
C6—C4—C3	113.88 (7)	C11—C12—H12A	109.5
C4—C5—O1	120.88 (8)	C11—C12—H12B	109.5
C4—C5—C10	130.87 (9)	H12A—C12—H12B	109.5
O1—C5—C10	108.23 (7)	C11—C12—H12C	109.5
O2—C6—O3	122.42 (8)	H12A—C12—H12C	109.5
O2—C6—C4	122.32 (9)	H12B—C12—H12C	109.5
O3—C6—C4	115.19 (7)	C11—C13—H13A	109.5
O3—C7—C8	107.55 (10)	C11—C13—H13B	109.5
O3—C7—H7A	110.2	H13A—C13—H13B	109.5
C8—C7—H7A	110.2	C11—C13—H13C	109.5
O3—C7—H7B	110.2	H13A—C13—H13C	109.5
C8—C7—H7B	110.2	H13B—C13—H13C	109.5
H7A—C7—H7B	108.5
C5—O1—C1—N2	−165.46 (8)	C6—C4—C5—C10	1.72 (18)
C5—O1—C1—C2	14.55 (14)	C3—C4—C5—C10	−178.70 (10)
N2—C1—C2—C9	7.28 (17)	C1—O1—C5—C4	−18.29 (14)
O1—C1—C2—C9	−172.73 (9)	C1—O1—C5—C10	160.34 (9)
N2—C1—C2—C3	−172.47 (10)	C7—O3—C6—O2	0.41 (16)
O1—C1—C2—C3	7.52 (15)	C7—O3—C6—C4	177.50 (9)
C1—C2—C3—C4	−23.01 (13)	C5—C4—C6—O2	−155.83 (11)
C9—C2—C3—C4	157.24 (9)	C3—C4—C6—O2	24.56 (14)
C1—C2—C3—C11	101.52 (11)	C5—C4—C6—O3	27.08 (14)
C9—C2—C3—C11	−78.22 (11)	C3—C4—C6—O3	−152.53 (9)
C2—C3—C4—C5	19.51 (13)	C6—O3—C7—C8	179.26 (11)
C11—C3—C4—C5	−107.12 (10)	C4—C3—C11—C13	−167.94 (8)
C2—C3—C4—C6	−160.87 (8)	C2—C3—C11—C13	68.32 (10)
C11—C3—C4—C6	72.50 (9)	C4—C3—C11—C12	66.72 (11)
C3—C4—C5—O1	−0.42 (14)	C2—C3—C11—C12	−57.03 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.08	2.9411 (11)	174
N2—H2B···N3ii	0.86	2.19	3.0269 (13)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.08	2.9411 (11)	174
N2—H2B⋯N3ii	0.86	2.19	3.0269 (13)	164

Symmetry codes: (i) ; (ii) .