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

Gangadharan, R.; Sethusankar, K.; Murugan, G.; Bakthadoss, M.

doi:10.1107/S1600536811021829

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1695

doi:10.1107/S1600536811021829

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

Rajeswari Gangadharan,^a K. Sethusankar,^b ^* Gandhi Murugan ^c and Manickam Bakthadoss ^c

^aDepartment of Physics, Ethiraj College for Women (Autonomous), Chennai 600 008, India, ^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 13 May 2011; accepted 6 June 2011; online 18 June 2011)

In the title compound, C₁₉H₁₈N₂O₂, 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 intermolecular C—H⋯π interactions.

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_r = 306.35
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.04
3606 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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

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/S1600536811021829/rk2276sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811021829/rk2276Isup3.cml

checkCIF report

Comment top

Chromenopyrroles are used in the treatment of Parkinsons disease (Carlson, 1993) and memory disorders(Sokoloff et al., 1990). Isoxazoline derivatives have been shown to be efficient precursors for many synthetic intermediates including γ-amino alchols and β-hydroxy ketones (Kozikowski, 1984). Spiroisoxazolines display interesting biological properties such as herbicidal, plant growth regulators and antitumour activities (Howe & Shelton, 1990). These observations prompted us to synthesize the title compound with fused chromeno and isoxazole rings (Bakthadoss & Murugan, 2010).

In the title molecule (Fig 1), the fused benzene and pyran rings forming the chromeno system are inclined to one another at a dihedral angle of 4.47 (7)° between the best planes of the rings. The six membered pyran ring adopts a half chair conformation with puckering amplitude Q= 0.4782 (15)Å, θ = 50.93 (17)° and ϕ = 278.3 (2)° (Cremer & Pople, 1975). In the pyran ring the C—C bond distances vary from a minimum of 1.3901 (19)Å to a maximum of 1.5332 (19)Å in comparison with a typical aromatic bond length of 1.384 (13)Å (Allen et al., 1987). This could be attributed to the presence of the heteroatom O1 in the cyclic system and also to the fusion of the pyran and isoxazole ring systems (Rybarczyk-Pirek et al., 2002).

The fusion between the isoxazole and the pyran rings at C7 and C8 is in cis-form. The dihedral angle between the fused chromeno and the isoxazole moieties is 43.71 (7)°.

The isoxazole ring adopts an envelope conformation at N1 with puckering parameters q2 = 0.5179 (14)Å and ϕ2 = 217.11 (16)° (Cremer & Pople,1975). In the isoxazole ring, enlargement of bond lengths and bond angles are observed at the points of linkages of substituents and fusion to the pyran ring (Raju et al., 2002).

The phenyl ring (C12–C17) substituent is almost perpendicular to the five membered isoxazole ring, the dihedral angle between them being 81.26 (8)°. The geometric parameters of the title compound agree well with reported structure (Gangadharan et al., 2011).

The crystal packing is stabilized by C—H···C and C—H···π interactions (C3—H···Cg3, where Cg3 is the centroid of the six membered ring defined by atoms C1–C6). The symmetry codes are: (i) x, y-1, z; (ii) -x, 1/2+y, 1/2-z. The packing view of the title compound shown in Fig. 2.

Related literature top

For the uses of chromeno derivatives, see: Carlson (1993); Sokoloff et al. (1990) and for the 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 distorsions, see: Rybarczyk-Pirek et al. (2002); Allen et al. (1987); Raju et al. (2002); For the synthesis of isoxazolidines, see: Bakthadoss & Murugan (2010).

Experimental top

A mixture of compound (E)-2-((2-formylphenoxy)methyl)-3-p-tolylacylonitrile (1 mmol) with 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), dilute HCl (5 ml) and extracted with ethylacetate (20 ml). The organic layer was washed with brine solution (10 ml) and concentrated. The crude product was purified by column chromatography to provide the pure desired product as colourless solid.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (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 presented as small spheres of arbitary radius.
	Fig. 2. Formation of C—H···C intermolecular bonding in the title compound.

1-Methyl-3-p-tolyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c] isoxazole-3a-carbonitrile top

Crystal data top

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

Data collection top

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

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0533P)² + 0.223P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₉H₁₈N₂O₂	V = 1599.62 (10) Å³
M_r = 306.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5344 (3) Å	µ = 0.08 mm⁻¹
b = 7.6980 (3) Å	T = 295 K
c = 24.6017 (8) Å	0.30 × 0.25 × 0.25 mm
β = 98.234 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2571 reflections with I > 2σ(I)
16796 measured reflections	R_int = 0.030
3606 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
3606 reflections	Δρ_min = −0.14 e Å⁻³
210 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₂O₂
M_r	306.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.5344 (3), 7.6980 (3), 24.6017 (8)
β (°)	98.234 (2)
V (Å³)	1599.62 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16796, 3606, 2571
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.04
No. of reflections	3606
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

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

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

Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2.

Acknowledgements

RG and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Rybarczyk-Pirek, A. J., Małecka, M., Grabowski, S. J. & Nawrot-Modranka, J. (2002). Acta Cryst. C58, o405–o406. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 7| July 2011| Page o1695

doi:10.1107/S1600536811021829

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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