1-Methyl-3-p-tolyl-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile.

In the title compound, C(19)H(18)N(2)O(2), the dihedral angle between the mean planes of the fused chromeno and isoxazole units is 43.71 (7)°. The isoxazole and pyran rings exhibit envelope and half chair conformations, respectively. The crystal packing is stabilized by inter-molecular C-H⋯π inter-actions.

Related literature

For uses of chromeno derivatives, see: Carlson (1993 ▶); Sokoloff et al. (1990 ▶) and for uses of isoxazole derivatives, see: Kozikowski (1984 ▶); Howe & Shelton (1990 ▶). For a related structure, see: Gangadharan et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For bond-length and bond-angle distortions, see: Rybarczyk-Pirek et al. (2002 ▶); Allen et al. (1987 ▶); Raju et al. (2002 ▶); For the synthesis of isoxazolidines, see: Bakthadoss & Murugan (2010 ▶).

Experimental

Crystal data

C19H18N2O2

M = 306.35

Monoclinic,

a = 8.5344 (3) Å

b = 7.6980 (3) Å

c = 24.6017 (8) Å

β = 98.234 (2)°

V = 1599.62 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

16796 measured reflections

3606 independent reflections

2571 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.04

3606 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 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 datablock(s) global, I. DOI: 10.1107/S1600536811021829/rk2276sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021829/rk2276Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021829/rk2276Isup3.cml

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

C19H18N2O2	F(000) = 648
Mr = 306.35	Dx = 1.272 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3606 reflections
a = 8.5344 (3) Å	θ = 1.0–27.4°
b = 7.6980 (3) Å	µ = 0.08 mm−1
c = 24.6017 (8) Å	T = 295 K
β = 98.234 (2)°	Block, colourless
V = 1599.62 (10) Å3	0.30 × 0.25 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2571 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 27.4°, θmin = 2.4°
ω–scans	h = −10→11
16796 measured reflections	k = −9→9
3606 independent reflections	l = −31→31

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.223P] where P = (Fo2 + 2Fc2)/3
3606 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.22956 (16)	0.74379 (19)	0.22503 (6)	0.0473 (3)
C2	0.20315 (19)	0.8782 (2)	0.25995 (6)	0.0580 (4)
H2	0.2518	0.8771	0.2963	0.070*
C3	0.1058 (2)	1.0123 (2)	0.24110 (8)	0.0655 (5)
H3	0.0882	1.1022	0.2647	0.079*
C4	0.0333 (2)	1.0157 (2)	0.18741 (8)	0.0661 (5)
H4	−0.0330	1.1073	0.1747	0.079*
C5	0.05999 (17)	0.8817 (2)	0.15272 (7)	0.0559 (4)
H5	0.0123	0.8851	0.1163	0.067*
C6	0.15635 (15)	0.74186 (18)	0.17079 (5)	0.0436 (3)
C7	0.19011 (15)	0.60029 (18)	0.13206 (5)	0.0437 (3)
H7	0.2107	0.6513	0.0973	0.052*
C8	0.33071 (16)	0.48679 (18)	0.15615 (5)	0.0442 (3)
C9	0.32444 (19)	0.4600 (2)	0.21731 (6)	0.0540 (4)
H9A	0.2260	0.4026	0.2219	0.065*
H9B	0.4110	0.3849	0.2326	0.065*
C10	0.29378 (17)	0.3102 (2)	0.12512 (6)	0.0527 (4)
H10	0.2751	0.2212	0.1519	0.063*
C11	−0.07140 (19)	0.5205 (3)	0.08314 (8)	0.0816 (6)
H11A	−0.0377	0.5647	0.0502	0.122*
H11B	−0.1272	0.6096	0.0998	0.122*
H11C	−0.1402	0.4227	0.0743	0.122*
C12	0.41716 (17)	0.24478 (18)	0.09254 (6)	0.0474 (3)
C13	0.43199 (19)	0.3076 (2)	0.04099 (6)	0.0570 (4)
H13	0.3610	0.3903	0.0246	0.068*
C14	0.5515 (2)	0.2484 (2)	0.01362 (6)	0.0594 (4)
H14	0.5591	0.2913	−0.0212	0.071*
C15	0.65985 (18)	0.1273 (2)	0.03664 (6)	0.0540 (4)
C16	0.64196 (19)	0.0627 (2)	0.08744 (7)	0.0602 (4)
H16	0.7124	−0.0210	0.1036	0.072*
C17	0.52204 (19)	0.1192 (2)	0.11499 (6)	0.0564 (4)
H17	0.5117	0.0722	0.1491	0.068*
C18	0.7938 (2)	0.0675 (3)	0.00727 (8)	0.0795 (6)
H18A	0.7638	0.0806	−0.0316	0.119*
H18B	0.8165	−0.0525	0.0157	0.119*
H18C	0.8862	0.1362	0.0191	0.119*
C19	0.47926 (17)	0.57010 (19)	0.14768 (6)	0.0469 (3)
N1	0.06659 (14)	0.46627 (17)	0.12132 (5)	0.0582 (4)
N2	0.59187 (16)	0.64169 (19)	0.14207 (6)	0.0678 (4)
O1	0.33511 (13)	0.61910 (14)	0.24647 (4)	0.0597 (3)
O2	0.14917 (12)	0.34224 (16)	0.08996 (5)	0.0686 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0414 (8)	0.0510 (8)	0.0507 (8)	−0.0054 (6)	0.0103 (6)	−0.0034 (6)
C2	0.0541 (9)	0.0643 (10)	0.0576 (9)	−0.0120 (8)	0.0154 (7)	−0.0173 (8)
C3	0.0567 (10)	0.0600 (10)	0.0846 (12)	−0.0077 (8)	0.0269 (9)	−0.0238 (9)
C4	0.0535 (9)	0.0552 (10)	0.0924 (13)	0.0099 (8)	0.0198 (9)	−0.0044 (9)
C5	0.0453 (8)	0.0591 (10)	0.0635 (9)	0.0059 (7)	0.0086 (7)	−0.0008 (7)
C6	0.0345 (7)	0.0484 (8)	0.0494 (7)	−0.0031 (6)	0.0114 (5)	−0.0031 (6)
C7	0.0363 (7)	0.0498 (8)	0.0451 (7)	0.0003 (6)	0.0063 (5)	−0.0022 (6)
C8	0.0403 (7)	0.0442 (8)	0.0485 (7)	0.0010 (6)	0.0077 (6)	−0.0006 (6)
C9	0.0603 (9)	0.0506 (9)	0.0511 (8)	0.0042 (7)	0.0078 (7)	0.0046 (7)
C10	0.0504 (9)	0.0462 (8)	0.0630 (9)	−0.0033 (7)	0.0137 (7)	−0.0057 (7)
C11	0.0406 (9)	0.1028 (15)	0.0972 (13)	0.0017 (9)	−0.0049 (8)	−0.0387 (12)
C12	0.0488 (8)	0.0407 (8)	0.0528 (8)	−0.0017 (6)	0.0076 (6)	−0.0052 (6)
C13	0.0638 (10)	0.0455 (8)	0.0614 (9)	0.0078 (7)	0.0084 (7)	0.0074 (7)
C14	0.0741 (11)	0.0536 (9)	0.0529 (8)	−0.0037 (8)	0.0173 (8)	0.0015 (7)
C15	0.0541 (9)	0.0487 (9)	0.0603 (9)	−0.0047 (7)	0.0122 (7)	−0.0128 (7)
C16	0.0563 (9)	0.0580 (10)	0.0644 (10)	0.0141 (8)	0.0026 (7)	−0.0008 (8)
C17	0.0637 (10)	0.0576 (9)	0.0474 (8)	0.0064 (8)	0.0057 (7)	0.0036 (7)
C18	0.0744 (12)	0.0772 (13)	0.0927 (13)	−0.0026 (10)	0.0327 (10)	−0.0224 (10)
C19	0.0395 (8)	0.0453 (8)	0.0549 (8)	0.0063 (7)	0.0038 (6)	0.0034 (6)
N1	0.0395 (7)	0.0621 (8)	0.0736 (8)	−0.0039 (6)	0.0095 (6)	−0.0215 (7)
N2	0.0468 (8)	0.0640 (9)	0.0923 (10)	−0.0020 (7)	0.0093 (7)	0.0111 (8)
O1	0.0649 (7)	0.0651 (7)	0.0462 (5)	0.0059 (6)	−0.0022 (5)	−0.0047 (5)
O2	0.0461 (6)	0.0732 (8)	0.0851 (8)	−0.0001 (6)	0.0041 (5)	−0.0351 (6)

C1—O1	1.3692 (18)	C10—C12	1.4989 (19)
C1—C2	1.384 (2)	C10—H10	0.9800
C1—C6	1.3901 (19)	C11—N1	1.458 (2)
C2—C3	1.364 (2)	C11—H11A	0.9600
C2—H2	0.9300	C11—H11B	0.9600
C3—C4	1.376 (2)	C11—H11C	0.9600
C3—H3	0.9300	C12—C17	1.378 (2)
C4—C5	1.378 (2)	C12—C13	1.380 (2)
C4—H4	0.9300	C13—C14	1.378 (2)
C5—C6	1.389 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.377 (2)
C6—C7	1.5025 (19)	C14—H14	0.9300
C7—N1	1.4716 (18)	C15—C16	1.374 (2)
C7—C8	1.5332 (19)	C15—C18	1.509 (2)
C7—H7	0.9800	C16—C17	1.376 (2)
C8—C19	1.462 (2)	C16—H16	0.9300
C8—C9	1.5272 (19)	C17—H17	0.9300
C8—C10	1.569 (2)	C18—H18A	0.9600
C9—O1	1.4155 (18)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700	C19—N2	1.1333 (18)
C10—O2	1.4235 (18)	N1—O2	1.4694 (16)
O1—C1—C2	116.22 (13)	O2—C10—H10	108.6
O1—C1—C6	122.86 (13)	C12—C10—H10	108.6
C2—C1—C6	120.87 (14)	C8—C10—H10	108.6
C3—C2—C1	120.02 (15)	N1—C11—H11A	109.5
C3—C2—H2	120.0	N1—C11—H11B	109.5
C1—C2—H2	120.0	H11A—C11—H11B	109.5
C2—C3—C4	120.58 (15)	N1—C11—H11C	109.5
C2—C3—H3	119.7	H11A—C11—H11C	109.5
C4—C3—H3	119.7	H11B—C11—H11C	109.5
C3—C4—C5	119.26 (16)	C17—C12—C13	118.32 (14)
C3—C4—H4	120.4	C17—C12—C10	119.16 (13)
C5—C4—H4	120.4	C13—C12—C10	122.51 (14)
C4—C5—C6	121.65 (15)	C14—C13—C12	120.32 (15)
C4—C5—H5	119.2	C14—C13—H13	119.8
C6—C5—H5	119.2	C12—C13—H13	119.8
C5—C6—C1	117.59 (13)	C15—C14—C13	121.60 (14)
C5—C6—C7	121.19 (12)	C15—C14—H14	119.2
C1—C6—C7	121.06 (13)	C13—C14—H14	119.2
N1—C7—C6	115.14 (11)	C16—C15—C14	117.62 (14)
N1—C7—C8	99.83 (11)	C16—C15—C18	121.05 (16)
C6—C7—C8	112.25 (11)	C14—C15—C18	121.33 (16)
N1—C7—H7	109.7	C15—C16—C17	121.40 (15)
C6—C7—H7	109.7	C15—C16—H16	119.3
C8—C7—H7	109.7	C17—C16—H16	119.3
C19—C8—C9	110.68 (12)	C16—C17—C12	120.70 (14)
C19—C8—C7	109.97 (11)	C16—C17—H17	119.7
C9—C8—C7	108.78 (11)	C12—C17—H17	119.7
C19—C8—C10	115.37 (12)	C15—C18—H18A	109.5
C9—C8—C10	109.25 (12)	C15—C18—H18B	109.5
C7—C8—C10	102.36 (11)	H18A—C18—H18B	109.5
O1—C9—C8	111.94 (12)	C15—C18—H18C	109.5
O1—C9—H9A	109.2	H18A—C18—H18C	109.5
C8—C9—H9A	109.2	H18B—C18—H18C	109.5
O1—C9—H9B	109.2	N2—C19—C8	176.76 (16)
C8—C9—H9B	109.2	C11—N1—O2	104.57 (12)
H9A—C9—H9B	107.9	C11—N1—C7	114.00 (14)
O2—C10—C12	110.34 (12)	O2—N1—C7	99.48 (10)
O2—C10—C8	104.01 (11)	C1—O1—C9	114.86 (11)
C12—C10—C8	116.36 (12)	C10—O2—N1	103.46 (10)
O1—C1—C2—C3	176.76 (13)	C9—C8—C10—C12	−123.06 (14)
C6—C1—C2—C3	−0.8 (2)	C7—C8—C10—C12	121.75 (13)
C1—C2—C3—C4	−0.1 (2)	O2—C10—C12—C17	−142.83 (14)
C2—C3—C4—C5	0.0 (2)	C8—C10—C12—C17	99.01 (16)
C3—C4—C5—C6	1.0 (2)	O2—C10—C12—C13	38.3 (2)
C4—C5—C6—C1	−1.9 (2)	C8—C10—C12—C13	−79.82 (18)
C4—C5—C6—C7	−177.41 (14)	C17—C12—C13—C14	−1.5 (2)
O1—C1—C6—C5	−175.61 (13)	C10—C12—C13—C14	177.30 (14)
C2—C1—C6—C5	1.8 (2)	C12—C13—C14—C15	−0.6 (3)
O1—C1—C6—C7	−0.1 (2)	C13—C14—C15—C16	2.0 (2)
C2—C1—C6—C7	177.32 (13)	C13—C14—C15—C18	−177.88 (15)
C5—C6—C7—N1	−81.82 (17)	C14—C15—C16—C17	−1.3 (2)
C1—C6—C7—N1	102.86 (15)	C18—C15—C16—C17	178.64 (16)
C5—C6—C7—C8	164.86 (13)	C15—C16—C17—C12	−0.9 (3)
C1—C6—C7—C8	−10.46 (18)	C13—C12—C17—C16	2.3 (2)
N1—C7—C8—C19	154.67 (11)	C10—C12—C17—C16	−176.59 (14)
C6—C7—C8—C19	−82.87 (14)	C6—C7—N1—C11	77.26 (16)
N1—C7—C8—C9	−83.97 (13)	C8—C7—N1—C11	−162.35 (12)
C6—C7—C8—C9	38.50 (15)	C6—C7—N1—O2	−172.04 (11)
N1—C7—C8—C10	31.56 (12)	C8—C7—N1—O2	−51.65 (12)
C6—C7—C8—C10	154.02 (11)	C2—C1—O1—C9	161.37 (13)
C19—C8—C9—O1	60.05 (16)	C6—C1—O1—C9	−21.07 (19)
C7—C8—C9—O1	−60.88 (15)	C8—C9—O1—C1	52.08 (17)
C10—C8—C9—O1	−171.86 (12)	C12—C10—O2—N1	−157.88 (11)
C19—C8—C10—O2	−119.20 (13)	C8—C10—O2—N1	−32.38 (14)
C9—C8—C10—O2	115.38 (13)	C11—N1—O2—C10	172.10 (14)
C7—C8—C10—O2	0.19 (14)	C7—N1—O2—C10	54.09 (13)
C19—C8—C10—C12	2.36 (18)

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···C4i	0.98	2.84	3.662 (2)	143
C3—H3···Cg3ii	0.93	2.99	3.8075 (18)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg3i	0.93	2.99	3.8075 (18)	147

Symmetry code: (i) .