1-Methyl-3-(naphthalen-1-yl)-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile.

In the title compound, C(22)H(18)N(2)O(2), the pyran ring of the chromene unit is fused with an isoxazole ring, which adopts an N-envelope conformation with the N atom lying 1.3291 (14) Å from the mean plane of the remaining ring atoms [maximum deviation = 0.341 (2) Å]. The dihedral angle between the isoxazole and chromene units is 43.74 (8)° and that between the iosxazole ring and the naphthalene ring system is 58.82 (8)°. In the crystal, the molecules are linked by weak C-H⋯π inter-actions.

Related literature

For uses of isoxazole derivatives, see: Baraldi et al. (1987 ▶); Eddington et al. (2002 ▶); Caine (1993 ▶). For related structures, see: Swaminathan et al. (2011a ▶,b ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For the synthesis of isoxazolidines, see: Bakthadoss & Murugan (2010 ▶).

Experimental

Crystal data

C22H18N2O2

M = 342.38

Monoclinic,

a = 10.622 (6) Å

b = 12.969 (7) Å

c = 12.423 (7) Å

β = 93.64 (3)°

V = 1707.9 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

19983 measured reflections

4684 independent reflections

2767 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.176

S = 1.03

4684 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.31 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/S1600536811009731/pv2398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009731/pv2398Isup2.hkl

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

C22H18N2O2	F(000) = 720
Mr = 342.38	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4684 reflections
a = 10.622 (6) Å	θ = 1.0–25.0°
b = 12.969 (7) Å	µ = 0.09 mm−1
c = 12.423 (7) Å	T = 293 K
β = 93.64 (3)°	Block, colourless
V = 1707.9 (16) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
graphite	θmax = 29.6°, θmin = 2.3°
ω and φ scans	h = −13→14
19983 measured reflections	k = −17→13
4684 independent reflections	l = −17→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0917P)2] where P = (Fo2 + 2Fc2)/3
4684 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.31 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	0.14265 (14)	0.10109 (13)	0.82608 (15)	0.0435 (4)
C2	0.09651 (16)	0.01485 (15)	0.77009 (18)	0.0565 (5)
H2	0.0678	0.0207	0.6981	0.068*
C3	0.09339 (19)	−0.07866 (16)	0.8210 (2)	0.0711 (7)
H3	0.0634	−0.1364	0.7831	0.085*
C4	0.1342 (2)	−0.08753 (16)	0.9273 (2)	0.0764 (7)
H4	0.1317	−0.1510	0.9619	0.092*
C5	0.17889 (19)	−0.00189 (15)	0.98249 (19)	0.0634 (5)
H5	0.2053	−0.0082	1.0550	0.076*
C6	0.18571 (15)	0.09400 (13)	0.93287 (14)	0.0445 (4)
C7	0.23100 (15)	0.18759 (13)	0.99341 (13)	0.0423 (4)
H7	0.1947	0.1897	1.0640	0.051*
C8	0.20434 (14)	0.28953 (12)	0.93319 (12)	0.0378 (4)
C9	0.22192 (14)	0.27038 (13)	0.81394 (12)	0.0392 (4)
H9A	0.2069	0.3340	0.7741	0.047*
H9B	0.3082	0.2492	0.8051	0.047*
C10	0.30763 (15)	0.36307 (13)	0.98762 (13)	0.0429 (4)
H10	0.2653	0.4150	1.0298	0.051*
C11	0.4298 (2)	0.12639 (17)	1.08402 (16)	0.0642 (5)
H11A	0.5172	0.1446	1.0957	0.096*
H11B	0.4231	0.0572	1.0567	0.096*
H11C	0.3896	0.1307	1.1509	0.096*
C12	0.39286 (14)	0.41856 (12)	0.91194 (13)	0.0401 (4)
C13	0.51461 (16)	0.38596 (14)	0.90491 (16)	0.0503 (4)
H13	0.5434	0.3293	0.9452	0.060*
C14	0.59706 (16)	0.43657 (15)	0.83792 (19)	0.0583 (5)
H14	0.6797	0.4135	0.8349	0.070*
C15	0.55729 (17)	0.51739 (15)	0.77876 (18)	0.0571 (5)
H15	0.6122	0.5493	0.7338	0.069*
C16	0.43293 (16)	0.55539 (13)	0.78330 (15)	0.0478 (4)
C17	0.34944 (14)	0.50587 (12)	0.85222 (14)	0.0407 (4)
C18	0.22757 (16)	0.54867 (14)	0.85861 (17)	0.0520 (5)
H18	0.1719	0.5188	0.9043	0.062*
C19	0.19061 (18)	0.63210 (15)	0.7997 (2)	0.0651 (6)
H19	0.1107	0.6598	0.8066	0.078*
C20	0.2715 (2)	0.67751 (17)	0.7281 (2)	0.0702 (6)
H20	0.2438	0.7329	0.6854	0.084*
C21	0.3899 (2)	0.64047 (16)	0.72136 (19)	0.0632 (5)
H21	0.4437	0.6718	0.6750	0.076*
C22	0.07561 (16)	0.32612 (14)	0.94773 (14)	0.0465 (4)
N1	0.36917 (13)	0.19627 (11)	1.00702 (11)	0.0466 (4)
N2	−0.02444 (16)	0.35439 (15)	0.95782 (16)	0.0724 (5)
O1	0.13851 (10)	0.19321 (9)	0.77127 (9)	0.0466 (3)
O2	0.37728 (12)	0.29730 (9)	1.05968 (9)	0.0549 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0362 (8)	0.0388 (10)	0.0562 (10)	−0.0010 (7)	0.0092 (7)	−0.0039 (8)
C2	0.0412 (9)	0.0505 (12)	0.0780 (13)	−0.0054 (8)	0.0061 (8)	−0.0154 (10)
C3	0.0565 (12)	0.0434 (13)	0.114 (2)	−0.0055 (9)	0.0087 (12)	−0.0151 (13)
C4	0.0777 (14)	0.0374 (12)	0.115 (2)	−0.0021 (10)	0.0170 (14)	0.0093 (13)
C5	0.0695 (12)	0.0467 (12)	0.0752 (14)	0.0013 (10)	0.0127 (10)	0.0105 (10)
C6	0.0466 (9)	0.0365 (9)	0.0517 (10)	0.0020 (7)	0.0135 (7)	0.0023 (8)
C7	0.0519 (9)	0.0399 (10)	0.0359 (8)	0.0053 (7)	0.0096 (6)	0.0038 (7)
C8	0.0444 (8)	0.0361 (9)	0.0336 (7)	0.0011 (7)	0.0071 (6)	−0.0016 (6)
C9	0.0431 (8)	0.0393 (9)	0.0354 (8)	−0.0055 (7)	0.0042 (6)	−0.0016 (7)
C10	0.0529 (9)	0.0391 (9)	0.0362 (8)	0.0040 (7)	−0.0003 (7)	−0.0069 (7)
C11	0.0750 (13)	0.0671 (14)	0.0495 (10)	0.0200 (11)	−0.0032 (9)	0.0119 (10)
C12	0.0416 (8)	0.0352 (9)	0.0432 (8)	−0.0020 (7)	−0.0001 (6)	−0.0135 (7)
C13	0.0460 (9)	0.0395 (10)	0.0642 (11)	0.0005 (8)	−0.0052 (8)	−0.0161 (9)
C14	0.0360 (9)	0.0490 (12)	0.0904 (15)	−0.0050 (8)	0.0080 (9)	−0.0267 (11)
C15	0.0482 (10)	0.0473 (11)	0.0779 (14)	−0.0165 (9)	0.0190 (9)	−0.0205 (10)
C16	0.0469 (9)	0.0389 (10)	0.0581 (10)	−0.0141 (8)	0.0074 (7)	−0.0119 (8)
C17	0.0406 (8)	0.0335 (9)	0.0481 (9)	−0.0050 (7)	0.0029 (7)	−0.0130 (7)
C18	0.0459 (9)	0.0388 (10)	0.0722 (12)	−0.0047 (8)	0.0100 (8)	0.0003 (9)
C19	0.0521 (11)	0.0408 (11)	0.1023 (18)	0.0000 (9)	0.0031 (10)	0.0085 (11)
C20	0.0728 (13)	0.0424 (12)	0.0946 (17)	−0.0101 (10)	−0.0002 (11)	0.0163 (12)
C21	0.0678 (12)	0.0468 (12)	0.0761 (14)	−0.0185 (10)	0.0128 (10)	0.0061 (10)
C22	0.0514 (10)	0.0411 (10)	0.0484 (9)	0.0018 (8)	0.0144 (7)	0.0042 (8)
N1	0.0569 (8)	0.0431 (8)	0.0391 (7)	0.0073 (7)	−0.0033 (6)	−0.0012 (6)
N2	0.0580 (10)	0.0734 (13)	0.0884 (14)	0.0138 (9)	0.0257 (9)	0.0095 (10)
O1	0.0499 (7)	0.0446 (7)	0.0446 (6)	−0.0111 (5)	−0.0027 (5)	−0.0023 (5)
O2	0.0737 (8)	0.0497 (8)	0.0392 (6)	0.0062 (6)	−0.0134 (6)	−0.0071 (6)

C1—O1	1.374 (2)	C11—N1	1.440 (2)
C1—C6	1.379 (3)	C11—H11A	0.9600
C1—C2	1.390 (3)	C11—H11B	0.9600
C2—C3	1.369 (3)	C11—H11C	0.9600
C2—H2	0.9300	C12—C13	1.369 (2)
C3—C4	1.369 (4)	C12—C17	1.415 (2)
C3—H3	0.9300	C13—C14	1.408 (3)
C4—C5	1.374 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.333 (3)
C5—C6	1.392 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.414 (3)
C6—C7	1.491 (2)	C15—H15	0.9300
C7—N1	1.471 (2)	C16—C21	1.405 (3)
C7—C8	1.537 (2)	C16—C17	1.424 (2)
C7—H7	0.9800	C17—C18	1.415 (2)
C8—C22	1.469 (2)	C18—C19	1.351 (3)
C8—C9	1.525 (2)	C18—H18	0.9300
C8—C10	1.574 (2)	C19—C20	1.405 (3)
C9—O1	1.4171 (19)	C19—H19	0.9300
C9—H9A	0.9700	C20—C21	1.354 (3)
C9—H9B	0.9700	C20—H20	0.9300
C10—O2	1.411 (2)	C21—H21	0.9300
C10—C12	1.526 (2)	C22—N2	1.139 (2)
C10—H10	0.9800	N1—O2	1.4647 (19)
O1—C1—C6	122.21 (16)	N1—C11—H11A	109.5
O1—C1—C2	116.89 (17)	N1—C11—H11B	109.5
C6—C1—C2	120.85 (18)	H11A—C11—H11B	109.5
C3—C2—C1	120.0 (2)	N1—C11—H11C	109.5
C3—C2—H2	120.0	H11A—C11—H11C	109.5
C1—C2—H2	120.0	H11B—C11—H11C	109.5
C2—C3—C4	120.3 (2)	C13—C12—C17	119.45 (16)
C2—C3—H3	119.8	C13—C12—C10	119.56 (16)
C4—C3—H3	119.8	C17—C12—C10	120.94 (14)
C3—C4—C5	119.5 (2)	C12—C13—C14	121.28 (18)
C3—C4—H4	120.3	C12—C13—H13	119.4
C5—C4—H4	120.3	C14—C13—H13	119.4
C4—C5—C6	121.8 (2)	C15—C14—C13	120.33 (17)
C4—C5—H5	119.1	C15—C14—H14	119.8
C6—C5—H5	119.1	C13—C14—H14	119.8
C1—C6—C5	117.54 (18)	C14—C15—C16	121.06 (18)
C1—C6—C7	120.50 (15)	C14—C15—H15	119.5
C5—C6—C7	121.87 (17)	C16—C15—H15	119.5
N1—C7—C6	114.07 (13)	C21—C16—C15	121.58 (17)
N1—C7—C8	98.15 (12)	C21—C16—C17	119.37 (16)
C6—C7—C8	114.28 (14)	C15—C16—C17	119.05 (18)
N1—C7—H7	109.9	C12—C17—C18	123.59 (15)
C6—C7—H7	109.9	C12—C17—C16	118.78 (15)
C8—C7—H7	109.9	C18—C17—C16	117.61 (16)
C22—C8—C9	110.13 (13)	C19—C18—C17	121.28 (17)
C22—C8—C7	111.24 (13)	C19—C18—H18	119.4
C9—C8—C7	107.62 (13)	C17—C18—H18	119.4
C22—C8—C10	112.35 (14)	C18—C19—C20	120.70 (19)
C9—C8—C10	113.02 (13)	C18—C19—H19	119.7
C7—C8—C10	102.15 (13)	C20—C19—H19	119.7
O1—C9—C8	111.48 (12)	C21—C20—C19	119.9 (2)
O1—C9—H9A	109.3	C21—C20—H20	120.1
C8—C9—H9A	109.3	C19—C20—H20	120.1
O1—C9—H9B	109.3	C20—C21—C16	121.04 (18)
C8—C9—H9B	109.3	C20—C21—H21	119.5
H9A—C9—H9B	108.0	C16—C21—H21	119.5
O2—C10—C12	111.60 (14)	N2—C22—C8	179.3 (2)
O2—C10—C8	103.26 (14)	C11—N1—O2	104.78 (14)
C12—C10—C8	116.47 (13)	C11—N1—C7	115.42 (15)
O2—C10—H10	108.4	O2—N1—C7	98.62 (12)
C12—C10—H10	108.4	C1—O1—C9	115.41 (13)
C8—C10—H10	108.4	C10—O2—N1	104.11 (11)
O1—C1—C2—C3	−177.56 (15)	C8—C10—C12—C17	77.62 (19)
C6—C1—C2—C3	0.0 (3)	C17—C12—C13—C14	−1.1 (2)
C1—C2—C3—C4	0.8 (3)	C10—C12—C13—C14	−178.53 (15)
C2—C3—C4—C5	−0.3 (3)	C12—C13—C14—C15	−0.6 (3)
C3—C4—C5—C6	−0.9 (3)	C13—C14—C15—C16	1.2 (3)
O1—C1—C6—C5	176.25 (14)	C14—C15—C16—C21	−179.99 (18)
C2—C1—C6—C5	−1.2 (2)	C14—C15—C16—C17	−0.2 (3)
O1—C1—C6—C7	−0.5 (2)	C13—C12—C17—C18	−176.50 (16)
C2—C1—C6—C7	−177.92 (15)	C10—C12—C17—C18	0.9 (2)
C4—C5—C6—C1	1.7 (3)	C13—C12—C17—C16	2.1 (2)
C4—C5—C6—C7	178.34 (18)	C10—C12—C17—C16	179.54 (14)
C1—C6—C7—N1	−102.19 (17)	C21—C16—C17—C12	178.31 (16)
C5—C6—C7—N1	81.2 (2)	C15—C16—C17—C12	−1.5 (2)
C1—C6—C7—C8	9.6 (2)	C21—C16—C17—C18	−3.0 (2)
C5—C6—C7—C8	−166.94 (15)	C15—C16—C17—C18	177.18 (16)
N1—C7—C8—C22	−155.46 (13)	C12—C17—C18—C19	−179.89 (18)
C6—C7—C8—C22	83.44 (17)	C16—C17—C18—C19	1.5 (3)
N1—C7—C8—C9	83.82 (14)	C17—C18—C19—C20	1.5 (3)
C6—C7—C8—C9	−37.28 (17)	C18—C19—C20—C21	−3.0 (4)
N1—C7—C8—C10	−35.39 (14)	C19—C20—C21—C16	1.4 (3)
C6—C7—C8—C10	−156.49 (13)	C15—C16—C21—C20	−178.6 (2)
C22—C8—C9—O1	−61.53 (18)	C17—C16—C21—C20	1.6 (3)
C7—C8—C9—O1	59.89 (17)	C6—C7—N1—C11	−73.38 (19)
C10—C8—C9—O1	171.90 (13)	C8—C7—N1—C11	165.36 (14)
C22—C8—C10—O2	122.56 (14)	C6—C7—N1—O2	175.66 (12)
C9—C8—C10—O2	−112.06 (14)	C8—C7—N1—O2	54.40 (13)
C7—C8—C10—O2	3.27 (15)	C6—C1—O1—C9	23.1 (2)
C22—C8—C10—C12	−114.77 (15)	C2—C1—O1—C9	−159.34 (14)
C9—C8—C10—C12	10.62 (19)	C8—C9—O1—C1	−53.94 (18)
C7—C8—C10—C12	125.94 (14)	C12—C10—O2—N1	−94.92 (14)
O2—C10—C12—C13	13.2 (2)	C8—C10—O2—N1	30.93 (15)
C8—C10—C12—C13	−104.98 (17)	C11—N1—O2—C10	−174.85 (14)
O2—C10—C12—C17	−164.17 (13)	C7—N1—O2—C10	−55.57 (15)

Cg4 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···Cg4i	0.96	2.84	3.477 (2)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11C⋯Cg4i	0.96	2.84	3.477 (2)	125

Symmetry code: (i) .