1-Methyl-3-(2-methyl­phen­yl)-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c][1,2]oxazole-3a-carbonitrile

Swaminathan, K.; Sethusankar, K.; Murugan, G.; Bakthadoss, M.

doi:10.1107/S1600536811009378

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o905

doi:10.1107/S1600536811009378

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1-Methyl-3-(2-methylphenyl)-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c][1,2]oxazole-3a-carbonitrile

K. Swaminathan,^a K. Sethusankar,^a ^* G. Murugan ^b and M. Bakthadoss ^b

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 7 March 2011; accepted 11 March 2011; online 19 March 2011)

In the title compound, C₁₉H₁₈N₂O₂, 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 methylbenzene rings, respectively. The molecular structure is stabilized by weak C—H⋯π interactions.

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_r = 306.35
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.148
S = 1.01
5936 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound is an angularly substituted fused tricyclic chromenoisoxazolidine framework, synthesized using Baylis-Hillman derivatives through in situ formation of nitrones followed by an intramolecular (3 + 2) dipolar cycloaddition reaction sequence (Bakthadoss & Murugan, 2010). It is well known that benzopyran and isoxazolidine derivatives possess interesting biological and pharmacological activities (Lin et al., 1996; Hu et al., 2004). Leflunomide is an isoxazole drug used for the treatment of rheumatoid arthritis (Rozman et al., 2002).

The title compound (Fig. 1) comprises a chromenoisoxazole ring system attached to a methylbenzene ring and a carbonitrile group. The isoxazole ring (N1/O2/C7/C8/C10) adopts an N1 envelope conformation with N1 -0.3256 (11) Å out of the plane formed by the rest of the ring atoms. The isoxazole ring is inclined at 84.23 (7)° with respect to the mean-plane formed by methylbenzene ring (C11—C16). The pyran ring (O1/C1/C6-C9) adopts a half-chair conformation with puckering amplitudes (Cremer & Pople, 1975): Q = 0.4852 (13) Å, θ = 127.2 (2)° and ϕ = 107.9 (2)°. The title compound exhibits structural similarities with a reported structure (Swaminathan et al., 2011). The molecular structure of the title compound is stabilized by rather weak C18—H18B···π interactions involving the centroid (Cg1) of phenyl ring C11–C16 (Table 1).

Related literature top

For synthetic aspects, see: Bakthadoss et al. (2010). For 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 top

A mixture of (E)-2-((2-formylphenoxy) methyl) -3-o-tolylacrylonitrile (1.0 mmol), N-methylhydroxylamine hydrochloride (1.1 mmol), pyridine (0.24 ml, 3 mmol) and ethanol (5 ml) were placed in a round bottom flask and refluxed for 6 h. After completion of the reaction as indicated by TLC, the reaction mixture was concentrated under reduced pressure. The crude product was diluted with water (10 ml) and dil HCl (5 ml) and extracted with ethylacetate (20 ml). The organic layer was washed with brine solution (10 ml) and concetrated. The crude product was purified by column chromatography to provide the pure title compound, as a colourless solid. Crystals of the title compound were grown from its solution in methanol by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are drawn as small spheres of arbitary radius.

1-Methyl-3-(2-methylphenyl)-3,3a,4,9b-tetrahydro-1H- chromeno[4,3-c][1,2]oxazole-3a-carbonitrile top

Crystal data top

C₁₉H₁₈N₂O₂	F(000) = 648
M_r = 306.35	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0684P)² + 0.0556P] where P = (F_o² + 2F_c²)/3
5936 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₁₈N₂O₂	V = 1592.54 (9) Å³
M_r = 306.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0120 (4) Å	µ = 0.08 mm⁻¹
b = 13.0368 (4) Å	T = 293 K
c = 11.1977 (3) Å	0.30 × 0.25 × 0.20 mm
β = 97.836 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3084 reflections with I > 2σ(I)
23069 measured reflections	R_int = 0.035
5936 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
5936 reflections	Δρ_min = −0.21 e Å⁻³
210 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) −x+1/2, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₂O₂
M_r	306.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.0120 (4), 13.0368 (4), 11.1977 (3)
β (°)	97.836 (2)
V (Å³)	1592.54 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23069, 5936, 3084
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.769

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.148, 1.01
No. of reflections	5936
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) −x+1/2, y+1/2, −z−1/2.

Acknowledgements

K. Swaminathan and K. Sethusankar thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection.

References

Bakthadoss, M. & Murugan, G. (2010). Eur. J. Org. Chem. pp. 5825–5830. Web of Science CSD CrossRef Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hu, H., Harrison, T. J. & Wilson, P. D. (2004). J. Org. Chem. 69, 3782–3786. Web of Science CrossRef PubMed CAS Google Scholar
Lin, G. N., Lu, C. M., Lin, H. C., Fang, S. C., Shieh, B. J., Hsu, M. F., Wang, J. P., Ko, F. N. & Teng, C. M. (1996). J. Nat. Prod. 59, 834–838. CrossRef CAS PubMed Web of Science Google Scholar
Rozman, B., Praprotnik, S., Logar, D., Tomsic, M., Hojnik, M., Kos-Golja, M., Accetto, R. & Dolenc, P. (2002). Ann. Rheum. Dis. 61, 567–569. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o799. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 4| April 2011| Page o905

doi:10.1107/S1600536811009378

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Methyl-3-(2-methyl­phen­yl)-3,3a,4,9b-tetra­hydro-1H-chromeno[4,3-c][1,2]oxazole-3a-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Methyl-3-(2-methylphenyl)-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c][1,2]oxazole-3a-carbonitrile