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

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

doi:10.1107/S1600536811009731

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o942

doi:10.1107/S1600536811009731

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1-Methyl-3-(naphthalen-1-yl)-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, R.K.M. 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 7 March 2011; accepted 15 March 2011; online 23 March 2011)

In the title compound, C₂₂H₁₈N₂O₂, 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 interactions.

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_r = 342.38
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.176
S = 1.03
4684 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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

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/S1600536811009731/pv2398sup1.cif

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

checkCIF report

Comment top

Isoxazole and its derivates are key intermediates for the preparation of products which mimic natural compounds (Baraldi et al., 1987). They have been shown to possess anticonvulsant activity (Eddington et al., 2002). Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993).

In the title compound (Fig. 1), the isoxazole rings adopts an N1-envelope conformation; N1 lies 1.3291 (14) Å from the mean plane formed by the rest of the ring atoms. The dihedral angle between the isoxazole and chromeno moiety is 43.74 (8)°. The dihedral angle between the isoxazole and naphthalene ring system is 58.82 (8)°, indicating a bisectional orientation. The pyran ring (O1/C1/C6-C9) adopts a half-chair conformation with puckering amplitudes (Cremer & Pople, 1975): Q = 0.480 (2) Å, θ = 129.2 (2)° and ϕ = 101.2 (2)°. The title compound exhibits structural similarities with other reported structures (Swaminathan et al., 2011a,b). The molecular structure is stabilized by C–H···π interactions (C11–H11C···Cg4 where Cg4 is the centroid of the six membered ring defined by the atoms C12–C17) (Table 1).

Related literature top

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 related literature, see: Bakthadoss & Murugan (2010).

Experimental top

A mixture of (E)-2-((2-formylnaphthalen-3-yloxy) -3-phenylacrylonitrile (1 mmol), N-methylhydroxyamine hydrochloride (1.1 mmol), pyridine (0.24 mL, 3 mmol) and ethanol (5 mL) was 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 title compound as 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: 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 title compound showing 30% probability displacement ellipsoids.

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

Crystal data top

C₂₂H₁₈N₂O₂	F(000) = 720
M_r = 342.38	D_x = 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

Data collection top

Bruker APEXII CCD area-detector diffractometer	2767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 29.6°, θ_min = 2.3°
ω and ϕ scans	h = −13→14
19983 measured reflections	k = −17→13
4684 independent reflections	l = −17→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0917P)²] where P = (F_o² + 2F_c²)/3
4684 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₂H₁₈N₂O₂	V = 1707.9 (16) Å³
M_r = 342.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.622 (6) Å	µ = 0.09 mm⁻¹
b = 12.969 (7) Å	T = 293 K
c = 12.423 (7) Å	0.30 × 0.25 × 0.20 mm
β = 93.64 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2767 reflections with I > 2σ(I)
19983 measured reflections	R_int = 0.054
4684 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
4684 reflections	Δρ_min = −0.31 e Å⁻³
236 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	0.14265 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₂
M_r	342.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.622 (6), 12.969 (7), 12.423 (7)
β (°)	93.64 (3)
V (Å³)	1707.9 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19983, 4684, 2767
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.176, 1.03
No. of reflections	4684
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.31

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

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) x, −y−1/2, z−1/2.

Acknowledgements

RG and KS are grateful to Dr Babu Varghese, SAIF, IIT, Madras, for help with the data collection.

References

Bakthadoss, M. & Murugan, G. (2010). Eur. J. Org. Chem. pp. 5825–5830. Web of Science CSD CrossRef Google Scholar
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Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Caine, B. (1993). Science, 260, 1814–1816. CrossRef CAS PubMed Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Eddington, N. D., Cox, D. S., Roberts, R. R., Butcher, R. J., Edafiogho, I. O., Stables, J. P., Cooke, N., Goodwin, A. M., Smith, C. A. & Scott, K. R. (2002). Eur. J. Chem. 37, 635–648. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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. (2011a). Acta Cryst. E67, o799. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 67| Part 4| April 2011| Page o942

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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