1-Methyl-3-(2-methyl-phen-yl)-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c][1,2]oxazole-3a-carbonitrile.

In the title compound, C(19)H(18)N(2)O(2), the five-membered isoxazole ring adopts an envelope conformation and the deviation of the N atom from the mean plane of the isoxazole ring is -0.3256 (11) Å. The pyran ring adopts a half-chair conformation. The isoxazole ring forms dihedral angles of 44.07 (7) and 84.23 (7)° with the pyran and methyl-benzene rings, respectively. The mol-ecular structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For the synthesis of the title compound, see: Bakthadoss & Murugan (2010 ▶). For the biological and pharmacological activities of isoxazole derivatives, see: Hu et al. (2004 ▶); Lin et al. (1996 ▶); Rozman et al. (2002 ▶). For a related structure, see: Swaminathan et al. (2011 ▶). For puckering amplitudes, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H18N2O2

M = 306.35

Monoclinic,

a = 11.0120 (4) Å

b = 13.0368 (4) Å

c = 11.1977 (3) Å

β = 97.836 (2)°

V = 1592.54 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

23069 measured reflections

5936 independent reflections

3084 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.148

S = 1.01

5936 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009378/pv2397sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009378/pv2397Isup2.hkl

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

C19H18N2O2	F(000) = 648
Mr = 306.35	Dx = 1.278 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 5936 reflections
a = 11.0120 (4) Å	θ = 1.0–25°
b = 13.0368 (4) Å	µ = 0.08 mm−1
c = 11.1977 (3) Å	T = 293 K
β = 97.836 (2)°	Block, colourless
V = 1592.54 (9) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3084 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 33.1°, θmin = 2.4°
ω scans	h = −15→16
23069 measured reflections	k = −18→19
5936 independent reflections	l = −14→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0684P)2 + 0.0556P] where P = (Fo2 + 2Fc2)/3
5936 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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	0.38107 (11)	0.12807 (10)	0.10789 (11)	0.0446 (3)
C2	0.43271 (13)	0.21739 (11)	0.15852 (13)	0.0582 (4)
H2	0.4706	0.2178	0.2380	0.070*
C3	0.42782 (15)	0.30530 (12)	0.09094 (15)	0.0654 (4)
H3	0.4635	0.3652	0.1245	0.078*
C4	0.37052 (14)	0.30563 (12)	−0.02619 (15)	0.0640 (4)
H4	0.3685	0.3653	−0.0720	0.077*
C5	0.31626 (13)	0.21749 (10)	−0.07520 (13)	0.0536 (3)
H5	0.2754	0.2187	−0.1535	0.064*
C6	0.32143 (11)	0.12627 (9)	−0.00950 (10)	0.0425 (3)
C7	0.25834 (11)	0.03122 (9)	−0.06218 (10)	0.0407 (3)
H7	0.1745	0.0473	−0.0987	0.049*
C8	0.25759 (10)	−0.05625 (9)	0.02964 (10)	0.0396 (3)
C9	0.37624 (12)	−0.05094 (10)	0.11822 (11)	0.0458 (3)
H9A	0.3776	−0.1068	0.1756	0.055*
H9B	0.4458	−0.0593	0.0744	0.055*
C10	0.25780 (11)	−0.15460 (10)	−0.05147 (10)	0.0448 (3)
H10	0.3344	−0.1923	−0.0288	0.054*
C11	0.15148 (11)	−0.22621 (9)	−0.04883 (10)	0.0430 (3)
C12	0.03836 (12)	−0.19982 (11)	−0.11130 (12)	0.0528 (3)
H12	0.0313	−0.1411	−0.1589	0.063*
C13	−0.06361 (13)	−0.25916 (12)	−0.10388 (13)	0.0577 (4)
H13	−0.1390	−0.2407	−0.1462	0.069*
C14	−0.05336 (13)	−0.34544 (11)	−0.03398 (13)	0.0571 (4)
H14	−0.1221	−0.3854	−0.0278	0.069*
C15	0.05804 (14)	−0.37299 (10)	0.02683 (12)	0.0544 (3)
H15	0.0638	−0.4322	0.0735	0.065*
C16	0.16284 (12)	−0.31509 (10)	0.02085 (10)	0.0458 (3)
C17	0.28229 (15)	−0.35091 (13)	0.08907 (14)	0.0714 (4)
H17A	0.3372	−0.3698	0.0331	0.107*
H17B	0.2679	−0.4092	0.1376	0.107*
H17C	0.3181	−0.2966	0.1400	0.107*
C18	0.31258 (15)	0.02789 (12)	−0.26883 (11)	0.0624 (4)
H18A	0.3441	−0.0171	−0.3251	0.094*
H18B	0.3574	0.0912	−0.2641	0.094*
H18C	0.2275	0.0413	−0.2953	0.094*
C19	0.15272 (11)	−0.05003 (9)	0.09694 (11)	0.0439 (3)
N1	0.32585 (9)	−0.02011 (8)	−0.15097 (8)	0.0464 (3)
N2	0.07493 (11)	−0.04521 (10)	0.15340 (10)	0.0598 (3)
O1	0.38708 (8)	0.04332 (7)	0.18095 (7)	0.0501 (2)
O2	0.25538 (9)	−0.11520 (7)	−0.17000 (7)	0.0540 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0477 (6)	0.0468 (7)	0.0411 (6)	−0.0039 (5)	0.0120 (5)	−0.0003 (5)
C2	0.0646 (8)	0.0602 (9)	0.0508 (7)	−0.0107 (7)	0.0116 (6)	−0.0100 (7)
C3	0.0768 (10)	0.0492 (9)	0.0737 (10)	−0.0142 (7)	0.0224 (8)	−0.0106 (8)
C4	0.0764 (10)	0.0434 (8)	0.0756 (10)	−0.0011 (7)	0.0229 (8)	0.0065 (7)
C5	0.0592 (8)	0.0497 (8)	0.0530 (7)	0.0026 (6)	0.0116 (6)	0.0084 (6)
C6	0.0446 (6)	0.0427 (7)	0.0416 (6)	0.0008 (5)	0.0116 (5)	0.0013 (5)
C7	0.0426 (6)	0.0460 (7)	0.0341 (5)	−0.0010 (5)	0.0071 (4)	0.0045 (5)
C8	0.0436 (6)	0.0430 (7)	0.0332 (5)	−0.0024 (5)	0.0089 (4)	0.0016 (5)
C9	0.0518 (7)	0.0487 (7)	0.0370 (6)	−0.0009 (6)	0.0060 (5)	0.0052 (5)
C10	0.0519 (7)	0.0451 (7)	0.0392 (6)	0.0005 (5)	0.0128 (5)	−0.0001 (5)
C11	0.0529 (7)	0.0397 (7)	0.0379 (5)	−0.0008 (5)	0.0121 (5)	−0.0041 (5)
C12	0.0604 (8)	0.0440 (7)	0.0544 (7)	0.0017 (6)	0.0087 (6)	0.0031 (6)
C13	0.0516 (7)	0.0597 (9)	0.0617 (8)	−0.0006 (6)	0.0072 (6)	−0.0070 (7)
C14	0.0609 (8)	0.0535 (8)	0.0600 (8)	−0.0130 (7)	0.0192 (7)	−0.0093 (7)
C15	0.0768 (9)	0.0427 (7)	0.0461 (7)	−0.0094 (6)	0.0168 (6)	−0.0025 (6)
C16	0.0623 (8)	0.0398 (7)	0.0360 (6)	−0.0005 (6)	0.0098 (5)	−0.0036 (5)
C17	0.0772 (10)	0.0690 (11)	0.0641 (9)	−0.0002 (8)	−0.0049 (8)	0.0154 (8)
C18	0.0810 (10)	0.0714 (10)	0.0372 (6)	−0.0130 (8)	0.0161 (6)	0.0050 (6)
C19	0.0513 (7)	0.0423 (7)	0.0394 (6)	−0.0030 (5)	0.0102 (5)	0.0016 (5)
N1	0.0557 (6)	0.0498 (6)	0.0361 (5)	−0.0091 (5)	0.0146 (4)	0.0002 (4)
N2	0.0639 (7)	0.0652 (8)	0.0551 (7)	0.0023 (6)	0.0249 (6)	0.0060 (6)
O1	0.0622 (5)	0.0532 (6)	0.0340 (4)	−0.0076 (4)	0.0040 (4)	0.0004 (4)
O2	0.0737 (6)	0.0535 (6)	0.0374 (4)	−0.0161 (4)	0.0166 (4)	−0.0045 (4)

C1—O1	1.3710 (14)	C10—C11	1.5008 (17)
C1—C2	1.3830 (18)	C10—H10	0.9800
C1—C6	1.3872 (17)	C11—C12	1.3864 (18)
C2—C3	1.370 (2)	C11—C16	1.3928 (17)
C2—H2	0.9300	C12—C13	1.3754 (19)
C3—C4	1.376 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.366 (2)
C4—C5	1.374 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.367 (2)
C5—C6	1.3954 (17)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.3882 (18)
C6—C7	1.5015 (17)	C15—H15	0.9300
C7—N1	1.4800 (15)	C16—C17	1.5027 (19)
C7—C8	1.5363 (16)	C17—H17A	0.9600
C7—H7	0.9800	C17—H17B	0.9600
C8—C19	1.4647 (16)	C17—H17C	0.9600
C8—C9	1.5305 (16)	C18—N1	1.4498 (16)
C8—C10	1.5715 (17)	C18—H18A	0.9600
C9—O1	1.4124 (15)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700	C19—N2	1.1336 (16)
C10—O2	1.4201 (14)	N1—O2	1.4626 (13)
O1—C1—C2	116.76 (11)	O2—C10—H10	109.2
O1—C1—C6	122.00 (11)	C11—C10—H10	109.2
C2—C1—C6	121.18 (12)	C8—C10—H10	109.2
C3—C2—C1	119.65 (14)	C12—C11—C16	119.67 (11)
C3—C2—H2	120.2	C12—C11—C10	119.03 (11)
C1—C2—H2	120.2	C16—C11—C10	121.18 (11)
C2—C3—C4	120.50 (14)	C13—C12—C11	120.98 (13)
C2—C3—H3	119.8	C13—C12—H12	119.5
C4—C3—H3	119.8	C11—C12—H12	119.5
C5—C4—C3	119.73 (14)	C14—C13—C12	119.56 (13)
C5—C4—H4	120.1	C14—C13—H13	120.2
C3—C4—H4	120.1	C12—C13—H13	120.2
C4—C5—C6	121.18 (13)	C13—C14—C15	120.00 (13)
C4—C5—H5	119.4	C13—C14—H14	120.0
C6—C5—H5	119.4	C15—C14—H14	120.0
C1—C6—C5	117.72 (12)	C14—C15—C16	121.90 (13)
C1—C6—C7	121.34 (11)	C14—C15—H15	119.1
C5—C6—C7	120.85 (11)	C16—C15—H15	119.1
N1—C7—C6	112.90 (9)	C15—C16—C11	117.88 (12)
N1—C7—C8	99.38 (9)	C15—C16—C17	118.83 (12)
C6—C7—C8	113.21 (9)	C11—C16—C17	123.28 (12)
N1—C7—H7	110.3	C16—C17—H17A	109.5
C6—C7—H7	110.3	C16—C17—H17B	109.5
C8—C7—H7	110.3	H17A—C17—H17B	109.5
C19—C8—C9	109.11 (9)	C16—C17—H17C	109.5
C19—C8—C7	112.33 (9)	H17A—C17—H17C	109.5
C9—C8—C7	108.55 (9)	H17B—C17—H17C	109.5
C19—C8—C10	113.95 (9)	N1—C18—H18A	109.5
C9—C8—C10	110.06 (10)	N1—C18—H18B	109.5
C7—C8—C10	102.61 (9)	H18A—C18—H18B	109.5
O1—C9—C8	111.62 (10)	N1—C18—H18C	109.5
O1—C9—H9A	109.3	H18A—C18—H18C	109.5
C8—C9—H9A	109.3	H18B—C18—H18C	109.5
O1—C9—H9B	109.3	N2—C19—C8	177.11 (13)
C8—C9—H9B	109.3	C18—N1—O2	104.33 (9)
H9A—C9—H9B	108.0	C18—N1—C7	114.76 (11)
O2—C10—C11	109.16 (10)	O2—N1—C7	100.14 (8)
O2—C10—C8	104.11 (9)	C1—O1—C9	114.23 (9)
C11—C10—C8	115.69 (9)	C10—O2—N1	103.20 (8)
O1—C1—C2—C3	−178.84 (12)	C9—C8—C10—C11	123.40 (11)
C6—C1—C2—C3	−1.6 (2)	C7—C8—C10—C11	−121.21 (11)
C1—C2—C3—C4	0.9 (2)	O2—C10—C11—C12	−41.16 (15)
C2—C3—C4—C5	0.9 (2)	C8—C10—C11—C12	75.80 (14)
C3—C4—C5—C6	−2.0 (2)	O2—C10—C11—C16	142.76 (11)
O1—C1—C6—C5	177.60 (11)	C8—C10—C11—C16	−100.28 (13)
C2—C1—C6—C5	0.56 (18)	C16—C11—C12—C13	1.17 (19)
O1—C1—C6—C7	0.98 (18)	C10—C11—C12—C13	−174.97 (12)
C2—C1—C6—C7	−176.06 (11)	C11—C12—C13—C14	0.0 (2)
C4—C5—C6—C1	1.29 (19)	C12—C13—C14—C15	−0.8 (2)
C4—C5—C6—C7	177.93 (12)	C13—C14—C15—C16	0.5 (2)
C1—C6—C7—N1	−106.66 (12)	C14—C15—C16—C11	0.60 (19)
C5—C6—C7—N1	76.83 (14)	C14—C15—C16—C17	−179.31 (13)
C1—C6—C7—C8	5.29 (16)	C12—C11—C16—C15	−1.42 (17)
C5—C6—C7—C8	−171.23 (10)	C10—C11—C16—C15	174.63 (11)
N1—C7—C8—C19	−152.86 (9)	C12—C11—C16—C17	178.48 (13)
C6—C7—C8—C19	87.13 (12)	C10—C11—C16—C17	−5.46 (18)
N1—C7—C8—C9	86.40 (10)	C6—C7—N1—C18	−77.73 (13)
C6—C7—C8—C9	−33.60 (13)	C8—C7—N1—C18	162.04 (10)
N1—C7—C8—C10	−30.08 (10)	C6—C7—N1—O2	171.21 (9)
C6—C7—C8—C10	−150.08 (10)	C8—C7—N1—O2	50.98 (10)
C19—C8—C9—O1	−62.50 (12)	C2—C1—O1—C9	−157.77 (11)
C7—C8—C9—O1	60.20 (12)	C6—C1—O1—C9	25.06 (16)
C10—C8—C9—O1	171.77 (9)	C8—C9—O1—C1	−56.41 (13)
C19—C8—C10—O2	120.23 (10)	C11—C10—O2—N1	157.42 (9)
C9—C8—C10—O2	−116.84 (10)	C8—C10—O2—N1	33.34 (11)
C7—C8—C10—O2	−1.45 (11)	C18—N1—O2—C10	−173.44 (10)
C19—C8—C10—C11	0.47 (15)	C7—N1—O2—C10	−54.44 (11)

Cg1 is the centroid of the phenyl ring C11–C16.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···Cg1i	0.96	2.99	3.6831 (16)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯Cg1i	0.96	2.99	3.6831 (16)	130

Symmetry code: (i) .