(2S,5S,6R)-5-(4-Methyl-phen-yl)-3-phenyl-4,8-dioxa-3-aza-tricyclo-[7.4.0.0]trideca-1(13),9,11-triene-6-carbonitrile.

In the title compound, C(24)H(20)N(2)O(2), the six-membered pyran ring adopts a half-chair conformation with one C atom deviating from the mean plane of the remaining ring atoms by 0.654 (6) Å. The five-membered isoxazole ring adopts an N-envelope conformation with the N atom displaced by 0.742 (5) Å from the mean plane formed by the remaining ring atoms. The carbonitrile side chain is almost linear, with a C-C-N angle of 178.6 (5)°. The crystal packing is stabilized by inter-molecular C-H⋯N inter-actions, through bifurcated acceptor hydrogen bonds formed between the carbonitrile N atom and two alternate C atoms in the unsubstituted benzene ring. The mol-ecular structure and crystal packing are further stabilized by intra-molecular and inter-molecular C-H⋯π inter-actions.

Related literature

For uses of benzopyran and isoxazolidine derivatives, see: Green et al. (1982 ▶); Kashiwada et al. (2001 ▶); Mullen et al. (1988 ▶). For a related structure, see: Swaminathan et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For synthetic details, see: Bakthadoss & Murugan (2010 ▶).

Experimental

Crystal data

C24H20N2O2

M = 368.42

Orthorhombic,

a = 8.9890 (16) Å

b = 9.8432 (19) Å

c = 22.084 (4) Å

V = 1954.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.976, T max = 0.980

10510 measured reflections

4476 independent reflections

2396 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.252

S = 1.00

4476 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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/S1600536811055413/pv2496sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055413/pv2496Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055413/pv2496Isup3.cml

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

C24H20N2O2	F(000) = 776
Mr = 368.42	Dx = 1.252 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4476 reflections
a = 8.9890 (16) Å	θ = 1.8–27.7°
b = 9.8432 (19) Å	µ = 0.08 mm−1
c = 22.084 (4) Å	T = 293 K
V = 1954.0 (6) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	4476 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
graphite	Rint = 0.065
ω scans	θmax = 27.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→11
Tmin = 0.976, Tmax = 0.980	k = −9→12
10510 measured reflections	l = −28→28

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.252	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1392P)2 + 0.1028P] where P = (Fo2 + 2Fc2)/3
4476 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 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	0.7119 (5)	0.2084 (4)	0.21685 (18)	0.0428 (9)
C2	0.7325 (5)	0.0754 (4)	0.2349 (2)	0.0576 (12)
H2	0.6914	0.0050	0.2123	0.069*
C3	0.8128 (6)	0.0469 (5)	0.2855 (2)	0.0655 (14)
H3	0.8273	−0.0425	0.2977	0.079*
C4	0.8728 (6)	0.1533 (5)	0.3188 (2)	0.0605 (12)
H4	0.9273	0.1352	0.3537	0.073*
C5	0.8522 (5)	0.2841 (5)	0.30056 (17)	0.0522 (11)
H5	0.8937	0.3541	0.3232	0.063*
C6	0.7705 (4)	0.3161 (4)	0.24889 (16)	0.0414 (9)
C7	0.7539 (4)	0.4578 (4)	0.22771 (15)	0.0383 (9)
H7	0.8516	0.5017	0.2259	0.046*
C8	0.6754 (4)	0.4707 (4)	0.16629 (15)	0.0402 (9)
C9	0.5624 (5)	0.3556 (4)	0.1614 (2)	0.0533 (11)
H9A	0.4902	0.3641	0.1938	0.064*
H9B	0.5097	0.3632	0.1232	0.064*
C10	0.7823 (6)	0.4613 (5)	0.11672 (17)	0.0520 (11)
C11	0.5993 (5)	0.6120 (4)	0.17064 (17)	0.0459 (10)
H11	0.4913	0.5988	0.1703	0.055*
C12	0.6383 (5)	0.7144 (4)	0.12342 (16)	0.0448 (9)
C13	0.7633 (6)	0.7942 (5)	0.12838 (19)	0.0609 (13)
H13	0.8258	0.7839	0.1616	0.073*
C14	0.7971 (7)	0.8890 (5)	0.0848 (2)	0.0728 (15)
H14	0.8806	0.9436	0.0897	0.087*
C15	0.7101 (7)	0.9044 (5)	0.0344 (2)	0.0684 (15)
C16	0.5876 (7)	0.8215 (7)	0.0288 (2)	0.0774 (17)
H16	0.5266	0.8291	−0.0051	0.093*
C17	0.5550 (6)	0.7284 (6)	0.0726 (2)	0.0710 (15)
H17	0.4727	0.6724	0.0674	0.085*
C18	0.7427 (10)	1.0141 (8)	−0.0113 (3)	0.112 (3)
H18A	0.7231	0.9804	−0.0513	0.168*
H18B	0.8453	1.0404	−0.0083	0.168*
H18C	0.6805	1.0914	−0.0035	0.168*
C19	0.7143 (5)	0.5804 (4)	0.32222 (16)	0.0457 (10)
C20	0.6470 (6)	0.5344 (6)	0.37311 (17)	0.0678 (14)
H20	0.5608	0.4825	0.3703	0.081*
C21	0.7058 (8)	0.5643 (8)	0.4288 (2)	0.088 (2)
H21	0.6590	0.5329	0.4637	0.105*
C22	0.8317 (9)	0.6392 (7)	0.4334 (2)	0.091 (2)
H22	0.8712	0.6592	0.4713	0.110*
C23	0.9005 (8)	0.6853 (6)	0.3823 (2)	0.0874 (19)
H23	0.9874	0.7361	0.3853	0.105*
C24	0.8416 (6)	0.6567 (5)	0.3261 (2)	0.0658 (14)
H24	0.8877	0.6888	0.2912	0.079*
N1	0.6521 (4)	0.5396 (3)	0.26516 (13)	0.0454 (8)
N2	0.8669 (6)	0.4523 (5)	0.07901 (16)	0.0717 (13)
O1	0.6300 (4)	0.2284 (3)	0.16486 (13)	0.0585 (8)
O2	0.6411 (4)	0.6622 (3)	0.22807 (11)	0.0539 (8)

	U11	U22	U33	U12	U13	U23
C1	0.037 (2)	0.033 (2)	0.059 (2)	0.0030 (18)	0.0031 (18)	0.0012 (18)
C2	0.045 (3)	0.030 (2)	0.098 (3)	0.002 (2)	0.007 (3)	0.000 (2)
C3	0.051 (3)	0.041 (3)	0.105 (4)	0.006 (2)	0.014 (3)	0.023 (3)
C4	0.053 (3)	0.054 (3)	0.074 (3)	0.019 (3)	0.000 (2)	0.015 (2)
C5	0.053 (3)	0.046 (2)	0.057 (2)	0.007 (2)	−0.003 (2)	0.003 (2)
C6	0.034 (2)	0.039 (2)	0.0515 (19)	0.0039 (18)	0.0058 (16)	0.0040 (17)
C7	0.036 (2)	0.035 (2)	0.0440 (18)	0.0044 (17)	0.0030 (16)	−0.0010 (17)
C8	0.034 (2)	0.039 (2)	0.0475 (19)	0.0019 (18)	0.0014 (16)	0.0024 (17)
C9	0.048 (3)	0.045 (3)	0.067 (3)	−0.005 (2)	−0.008 (2)	−0.002 (2)
C10	0.066 (3)	0.048 (2)	0.0419 (19)	0.007 (2)	0.002 (2)	0.0000 (19)
C11	0.038 (2)	0.049 (2)	0.051 (2)	0.0084 (19)	−0.0003 (17)	0.0013 (19)
C12	0.041 (3)	0.044 (2)	0.0493 (19)	0.006 (2)	0.0000 (18)	0.0058 (18)
C13	0.060 (3)	0.057 (3)	0.065 (3)	0.002 (3)	−0.011 (2)	0.015 (2)
C14	0.067 (4)	0.057 (3)	0.095 (4)	−0.006 (3)	0.003 (3)	0.019 (3)
C15	0.082 (4)	0.059 (3)	0.064 (3)	0.023 (3)	0.010 (3)	0.020 (3)
C16	0.077 (4)	0.096 (5)	0.059 (3)	0.011 (4)	−0.011 (3)	0.024 (3)
C17	0.066 (4)	0.077 (4)	0.070 (3)	−0.008 (3)	−0.022 (2)	0.012 (3)
C18	0.126 (7)	0.102 (5)	0.108 (4)	0.023 (5)	0.016 (4)	0.055 (4)
C19	0.053 (3)	0.039 (2)	0.046 (2)	0.009 (2)	0.0059 (18)	0.0024 (18)
C20	0.062 (3)	0.091 (4)	0.050 (2)	0.001 (3)	0.009 (2)	0.007 (3)
C21	0.100 (5)	0.116 (6)	0.048 (3)	0.003 (5)	0.009 (3)	0.000 (3)
C22	0.135 (7)	0.083 (4)	0.056 (3)	−0.002 (5)	−0.016 (3)	−0.018 (3)
C23	0.117 (5)	0.068 (4)	0.077 (3)	−0.033 (4)	−0.016 (3)	−0.011 (3)
C24	0.085 (4)	0.052 (3)	0.061 (2)	−0.018 (3)	−0.001 (3)	−0.004 (2)
N1	0.046 (2)	0.0425 (19)	0.0473 (16)	0.0103 (18)	0.0050 (15)	0.0043 (15)
N2	0.076 (3)	0.083 (3)	0.056 (2)	0.017 (3)	0.009 (2)	0.003 (2)
O1	0.065 (2)	0.0405 (17)	0.0696 (18)	−0.0055 (16)	−0.0100 (16)	−0.0047 (14)
O2	0.067 (2)	0.0478 (17)	0.0469 (13)	0.0153 (17)	0.0043 (14)	0.0060 (13)

C1—C6	1.379 (5)	C12—C13	1.376 (6)
C1—O1	1.378 (5)	C13—C14	1.373 (6)
C1—C2	1.381 (5)	C13—H13	0.9300
C2—C3	1.360 (7)	C14—C15	1.369 (7)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.388 (7)	C15—C16	1.376 (8)
C3—H3	0.9300	C15—C18	1.507 (7)
C4—C5	1.362 (6)	C16—C17	1.364 (7)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.393 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.478 (5)	C18—H18B	0.9600
C7—N1	1.473 (5)	C18—H18C	0.9600
C7—C8	1.534 (5)	C19—C20	1.354 (6)
C7—H7	0.9800	C19—C24	1.371 (7)
C8—C10	1.459 (6)	C19—N1	1.436 (5)
C8—C9	1.526 (6)	C20—C21	1.371 (7)
C8—C11	1.553 (6)	C20—H20	0.9300
C9—O1	1.394 (5)	C21—C22	1.355 (10)
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C22—C23	1.365 (8)
C10—N2	1.131 (6)	C22—H22	0.9300
C11—O2	1.412 (5)	C23—C24	1.377 (7)
C11—C12	1.492 (5)	C23—H23	0.9300
C11—H11	0.9800	C24—H24	0.9300
C12—C17	1.357 (6)	N1—O2	1.461 (4)
C6—C1—O1	121.4 (3)	C13—C12—C11	121.5 (4)
C6—C1—C2	122.0 (4)	C12—C13—C14	120.8 (4)
O1—C1—C2	116.6 (4)	C12—C13—H13	119.6
C3—C2—C1	120.3 (4)	C14—C13—H13	119.6
C3—C2—H2	119.9	C15—C14—C13	121.2 (5)
C1—C2—H2	119.9	C15—C14—H14	119.4
C2—C3—C4	119.1 (4)	C13—C14—H14	119.4
C2—C3—H3	120.5	C14—C15—C16	117.7 (5)
C4—C3—H3	120.5	C14—C15—C18	120.9 (6)
C5—C4—C3	120.2 (4)	C16—C15—C18	121.3 (6)
C5—C4—H4	119.9	C17—C16—C15	120.4 (5)
C3—C4—H4	119.9	C17—C16—H16	119.8
C4—C5—C6	121.9 (4)	C15—C16—H16	119.8
C4—C5—H5	119.1	C12—C17—C16	122.5 (5)
C6—C5—H5	119.1	C12—C17—H17	118.8
C1—C6—C5	116.6 (4)	C16—C17—H17	118.8
C1—C6—C7	121.6 (3)	C15—C18—H18A	109.5
C5—C6—C7	121.7 (4)	C15—C18—H18B	109.5
N1—C7—C6	113.6 (3)	H18A—C18—H18B	109.5
N1—C7—C8	99.5 (3)	C15—C18—H18C	109.5
C6—C7—C8	113.8 (3)	H18A—C18—H18C	109.5
N1—C7—H7	109.8	H18B—C18—H18C	109.5
C6—C7—H7	109.8	C20—C19—C24	120.2 (4)
C8—C7—H7	109.8	C20—C19—N1	117.5 (4)
C10—C8—C9	109.8 (4)	C24—C19—N1	122.2 (4)
C10—C8—C7	110.8 (3)	C19—C20—C21	120.1 (6)
C9—C8—C7	107.9 (3)	C19—C20—H20	120.0
C10—C8—C11	113.1 (3)	C21—C20—H20	120.0
C9—C8—C11	112.1 (3)	C22—C21—C20	120.4 (5)
C7—C8—C11	102.8 (3)	C22—C21—H21	119.8
O1—C9—C8	111.9 (4)	C20—C21—H21	119.8
O1—C9—H9A	109.2	C23—C22—C21	119.8 (5)
C8—C9—H9A	109.2	C23—C22—H22	120.1
O1—C9—H9B	109.2	C21—C22—H22	120.1
C8—C9—H9B	109.2	C22—C23—C24	120.2 (6)
H9A—C9—H9B	107.9	C22—C23—H23	119.9
N2—C10—C8	178.6 (5)	C24—C23—H23	119.9
O2—C11—C12	109.2 (3)	C19—C24—C23	119.3 (5)
O2—C11—C8	104.6 (3)	C19—C24—H24	120.3
C12—C11—C8	117.3 (3)	C23—C24—H24	120.3
O2—C11—H11	108.5	C19—N1—O2	106.7 (3)
C12—C11—H11	108.5	C19—N1—C7	113.8 (3)
C8—C11—H11	108.5	O2—N1—C7	100.3 (3)
C17—C12—C13	117.3 (4)	C1—O1—C9	114.0 (3)
C17—C12—C11	121.2 (4)	C11—O2—N1	103.5 (3)
C6—C1—C2—C3	−0.1 (7)	C17—C12—C13—C14	3.3 (7)
O1—C1—C2—C3	179.6 (4)	C11—C12—C13—C14	−179.4 (5)
C1—C2—C3—C4	0.3 (7)	C12—C13—C14—C15	−1.8 (8)
C2—C3—C4—C5	−0.5 (8)	C13—C14—C15—C16	−0.1 (8)
C3—C4—C5—C6	0.4 (8)	C13—C14—C15—C18	176.3 (5)
O1—C1—C6—C5	−179.6 (3)	C14—C15—C16—C17	0.5 (9)
C2—C1—C6—C5	0.1 (6)	C18—C15—C16—C17	−176.0 (6)
O1—C1—C6—C7	−2.6 (6)	C13—C12—C17—C16	−3.0 (8)
C2—C1—C6—C7	177.1 (4)	C11—C12—C17—C16	179.7 (5)
C4—C5—C6—C1	−0.2 (6)	C15—C16—C17—C12	1.2 (9)
C4—C5—C6—C7	−177.2 (4)	C24—C19—C20—C21	0.2 (8)
C1—C6—C7—N1	109.5 (4)	N1—C19—C20—C21	176.7 (5)
C5—C6—C7—N1	−73.6 (5)	C19—C20—C21—C22	−0.3 (10)
C1—C6—C7—C8	−3.5 (5)	C20—C21—C22—C23	0.0 (11)
C5—C6—C7—C8	173.4 (3)	C21—C22—C23—C24	0.5 (10)
N1—C7—C8—C10	150.9 (3)	C20—C19—C24—C23	0.3 (8)
C6—C7—C8—C10	−87.8 (4)	N1—C19—C24—C23	−176.0 (5)
N1—C7—C8—C9	−88.8 (4)	C22—C23—C24—C19	−0.7 (9)
C6—C7—C8—C9	32.4 (4)	C20—C19—N1—O2	132.9 (4)
N1—C7—C8—C11	29.8 (4)	C24—C19—N1—O2	−50.7 (5)
C6—C7—C8—C11	151.0 (3)	C20—C19—N1—C7	−117.4 (4)
C10—C8—C9—O1	60.6 (4)	C24—C19—N1—C7	59.0 (5)
C7—C8—C9—O1	−60.3 (4)	C6—C7—N1—C19	75.1 (4)
C11—C8—C9—O1	−172.8 (3)	C8—C7—N1—C19	−163.5 (3)
C10—C8—C11—O2	−118.3 (4)	C6—C7—N1—O2	−171.3 (3)
C9—C8—C11—O2	116.9 (4)	C8—C7—N1—O2	−49.9 (3)
C7—C8—C11—O2	1.3 (4)	C6—C1—O1—C9	−24.7 (5)
C10—C8—C11—C12	2.8 (5)	C2—C1—O1—C9	155.6 (4)
C9—C8—C11—C12	−122.0 (4)	C8—C9—O1—C1	57.2 (5)
C7—C8—C11—C12	122.4 (4)	C12—C11—O2—N1	−158.9 (3)
O2—C11—C12—C17	−147.9 (4)	C8—C11—O2—N1	−32.6 (4)
C8—C11—C12—C17	93.4 (5)	C19—N1—O2—C11	172.2 (3)
O2—C11—C12—C13	34.9 (5)	C7—N1—O2—C11	53.3 (4)
C8—C11—C12—C13	−83.8 (5)

Cg1 and Cg2 are the centroids of the C19–C24 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1	0.93	2.99	3.701 (5)	134
C20—H20···Cg2i	0.93	2.95	3.803 (6)	153
C21—H21···N2ii	0.93	2.56	3.385 (6)	148
C23—H23···N2iii	0.93	2.62	3.466 (7)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19–C24 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1	0.93	2.99	3.701 (5)	134
C20—H20⋯Cg2i	0.93	2.95	3.803 (6)	153
C21—H21⋯N2ii	0.93	2.56	3.385 (6)	148
C23—H23⋯N2iii	0.93	2.62	3.466 (7)	151

Symmetry codes: (i) ; (ii) ; (iii) .