rac-6-Eth­oxy-3,3a,4,9b-tetra­hydro-1,3-diphenyl-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile

Paramasivam, S.; Srinivasan, J.; Seshadri, P.R.; Bakthadoss, M.

doi:10.1107/S160053681201906X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1660

doi:10.1107/S160053681201906X

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rac-6-Ethoxy-3,3a,4,9b-tetrahydro-1,3-diphenyl-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile

S. Paramasivam,^a J. Srinivasan,^b P. R. Seshadri ^a ^* and M. Bakthadoss ^b

^aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 20 April 2012; accepted 27 April 2012; online 5 May 2012)

The title compound, C₂₅H₂₂N₂O₃, with three stereogenic centres, crystallizes in a centrosymmetric space group as a racemate. The pyran ring adopts a sofa conformation and the five-membered isoxazole ring exhibits an envelope conformation. The dihedral angle between the benzene ring and the mean plane through the near coplanar atoms of the pyran ring is 10.54 (9)°. In the crystal, no significant intermolecular interactions are observed.

Related literature

For the biological activity of the title compound, see: Rozman et al. (2002 ); Winn et al. (1976 ). For N-atom hybridization, see: Beddoes et al. (1986 ). For conformational analysis and puckering parameters, see: Cremer & Pople, (1975 ). For related structures, see: Kanchanadevi et al. (2011 ); Swaminathan et al. (2012 ).

Experimental

Crystal data

C₂₅H₂₂N₂O₃
M_r = 398.45
Monoclinic, P 2₁ /c
a = 15.2994 (9) Å
b = 7.5421 (5) Å
c = 18.7248 (12) Å
β = 107.596 (4)°
V = 2059.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
18432 measured reflections
5109 independent reflections
2805 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.164
S = 1.04
5109 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681201906X/kp2408sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201906X/kp2408Isup3.hkl

Supporting information file. DOI: 10.1107/S160053681201906X/kp2408Isup3.cml

checkCIF report

Comment top

Isoxazole derivative is used for the treatment of rheumatoid arthritis (Rozman et al., 2002) whereas benzopyran derivatives exhibit anti-depressant activities (Winn et al., 1976). On this grounds, the title compound was chosen for X-ray structure analysis (Fig.1).

The pyran ring (O1/C1/C6—C9) adopts a sofa conformation with the puckering parameters (Cremer & Pople, 1975) being q₂=0.426 (1) Å, q₃=0.291 (1) Å, Q_T=0.516 (1) Å and the five-membered isoxazole ring (N1/O2/C7/C8/C11) adopts an envelope conformation with puckering parameters (Cremer & Pople, 1975) being q₂=0.521 (19) Å and Φ₂=219.3 (2)°. The dihedral angle between the pyran and the benzene rings (C1—C6) is 7.68 (5)°. Also the dihedral angle between the chromeno ring (fusion of benzene and pyran rings) and isoxazole ring is 40.31 (5)°.

In the chromenoisoxazole moiety, the dihedral angle between the benzene and isoxazole ring is 36.41 (5)° and the dihedral angle between the pyran and isoxazole ring is 42.56 (6)°.

The sum of the bond angles around N1 [321.17 (39)°] indicates sp³ hybridization (Beddoes et al.,1986).

The geometric parameters of the title compound (Fig. 1) agree well with the reported similar structures (Kanchanadevi et al., 2011; Swaminathan et al., 2012).

The molecular structure is stabilized by C— H··· N intramolecular interaction and the crystal packing is stabilised by C— H··· O and C— H··· N hydrogen bonds (Table 1).

Related literature top

For the biological activity of the title compound, see: Rozman et al. (2002); Winn et al. (1976). For N-atom hybridization, see: Beddoes et al. (1986). For conformational analysis and pukering parameters, see: Cremer & Pople, (1975). For related structures, see: Kanchanadevi et al. (2011); Swaminathan et al. (2012).

Experimental top

A mixture of (E)-2-((2-ethoxy-6-formylphenoxy)methyl)-3-phenylacrylonitrile (2 mmol, 0.61 g) and N-phenylhydroxylamine (3 mmol, 0.33 g) in ethanol (10 mL) was refluxed for 6 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (15 mL) and extracted with ethyl acetate (3 × 15 mL). The combined organic layer was washed with brine (3 × 15 mL) and dried over anhydrous Na₂SO₄, solvent was removed under reduced pressure. The crude mass was purified by column chromatography on silica gel (Acme 100–200 mesh), using ethyl acetate-hexane (1:9) to afford the pure compound as a colourless solid in 76% yield.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.

rac-6-Ethoxy-3,3a,4,9b-tetrahydro-1,3-diphenyl-1H- chromeno[4,3-c]isoxazole-3a-carbonitrile top

Crystal data top

C₂₅H₂₂N₂O₃	F(000) = 840
M_r = 398.45	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5109 reflections
a = 15.2994 (9) Å	θ = 1.4–28.3°
b = 7.5421 (5) Å	µ = 0.09 mm⁻¹
c = 18.7248 (12) Å	T = 298 K
β = 107.596 (4)°	Block, colourless
V = 2059.6 (2) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	2805 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 28.3°, θ_min = 1.4°
ω and ϕ scans	h = −20→20
18432 measured reflections	k = −10→10
5109 independent reflections	l = −20→24

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) = 0.164	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0749P)² + 0.2385P] where P = (F_o² + 2F_c²)/3
5109 reflections	(Δ/σ)_max = 0.008
271 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₅H₂₂N₂O₃	V = 2059.6 (2) Å³
M_r = 398.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.2994 (9) Å	µ = 0.09 mm⁻¹
b = 7.5421 (5) Å	T = 298 K
c = 18.7248 (12) Å	0.20 × 0.15 × 0.10 mm
β = 107.596 (4)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	2805 reflections with I > 2σ(I)
18432 measured reflections	R_int = 0.029
5109 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
5109 reflections	Δρ_min = −0.18 e Å⁻³
271 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
O1	0.74167 (9)	0.45965 (16)	0.72376 (7)	0.0602 (4)
O2	0.88519 (9)	−0.03937 (17)	0.68806 (7)	0.0612 (4)
O3	0.59365 (9)	0.65386 (17)	0.67710 (8)	0.0672 (4)
N1	0.81401 (10)	0.0634 (2)	0.63282 (8)	0.0543 (4)
C7	0.74962 (12)	0.0946 (2)	0.67721 (10)	0.0476 (4)
H7	0.7257	−0.0189	0.6887	0.057*
C8	0.81684 (12)	0.1717 (2)	0.74828 (10)	0.0514 (5)
C1	0.67024 (13)	0.3889 (2)	0.66889 (10)	0.0502 (4)
C6	0.67181 (12)	0.2174 (2)	0.64144 (9)	0.0483 (4)
C12	0.94613 (12)	−0.0419 (3)	0.82161 (11)	0.0556 (5)
C11	0.90766 (13)	0.0711 (3)	0.75323 (11)	0.0561 (5)
H11	0.9542	0.1573	0.7500	0.067*
C20	0.77892 (12)	−0.0486 (3)	0.56829 (11)	0.0548 (5)
C9	0.82649 (14)	0.3691 (2)	0.73450 (11)	0.0600 (5)
H9A	0.8727	0.4202	0.7770	0.072*
H9B	0.8466	0.3845	0.6905	0.072*
C2	0.59079 (13)	0.4927 (2)	0.64301 (10)	0.0542 (5)
C5	0.59528 (13)	0.1560 (3)	0.58543 (10)	0.0568 (5)
H5	0.5957	0.0426	0.5660	0.068*
C17	1.02141 (13)	0.0150 (3)	0.87856 (12)	0.0701 (6)
H17	1.0493	0.1221	0.8738	0.084*
C10	0.78370 (14)	0.1491 (3)	0.81384 (11)	0.0583 (5)
C3	0.51685 (14)	0.4285 (3)	0.58771 (11)	0.0620 (5)
H3	0.4646	0.4981	0.5695	0.074*
C18	0.50900 (15)	0.7498 (3)	0.66297 (12)	0.0695 (6)
H18A	0.4604	0.6702	0.6658	0.083*
H18B	0.4922	0.8014	0.6132	0.083*
C21	0.75973 (14)	0.0310 (3)	0.49899 (12)	0.0689 (6)
H21	0.7702	0.1517	0.4956	0.083*
C4	0.51968 (14)	0.2608 (3)	0.55889 (11)	0.0645 (5)
H4	0.4695	0.2189	0.5209	0.077*
N2	0.75559 (15)	0.1391 (3)	0.86341 (11)	0.0825 (6)
C13	0.90569 (15)	−0.2018 (3)	0.83037 (13)	0.0706 (6)
H13	0.8547	−0.2422	0.7928	0.085*
C24	0.72930 (16)	−0.3275 (3)	0.50900 (16)	0.0823 (7)
H24	0.7191	−0.4485	0.5120	0.099*
C25	0.76250 (14)	−0.2284 (3)	0.57391 (13)	0.0674 (6)
H25	0.7736	−0.2816	0.6206	0.081*
C14	0.94057 (18)	−0.3005 (3)	0.89414 (14)	0.0833 (7)
H14	0.9130	−0.4073	0.8997	0.100*
C23	0.71127 (16)	−0.2466 (4)	0.43976 (15)	0.0866 (8)
H23	0.6897	−0.3139	0.3964	0.104*
C22	0.72498 (16)	−0.0680 (4)	0.43459 (13)	0.0818 (7)
H22	0.7109	−0.0137	0.3879	0.098*
C19	0.52145 (18)	0.8905 (3)	0.71959 (13)	0.0847 (7)
H19A	0.4654	0.9562	0.7107	0.127*
H19B	0.5696	0.9688	0.7164	0.127*
H19C	0.5374	0.8383	0.7686	0.127*
C15	1.01620 (18)	−0.2420 (4)	0.94988 (14)	0.0872 (7)
H15	1.0403	−0.3102	0.9927	0.105*
C16	1.05552 (16)	−0.0852 (4)	0.94225 (14)	0.0865 (7)
H16	1.1060	−0.0449	0.9804	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0672 (8)	0.0368 (7)	0.0725 (8)	0.0015 (7)	0.0151 (7)	−0.0087 (6)
O2	0.0582 (7)	0.0561 (8)	0.0708 (8)	0.0089 (7)	0.0220 (6)	−0.0094 (7)
O3	0.0757 (9)	0.0444 (8)	0.0851 (9)	0.0107 (7)	0.0299 (7)	−0.0058 (7)
N1	0.0549 (9)	0.0488 (9)	0.0627 (9)	−0.0006 (8)	0.0231 (7)	−0.0060 (8)
C7	0.0520 (10)	0.0342 (9)	0.0616 (10)	−0.0033 (8)	0.0244 (8)	−0.0045 (8)
C8	0.0555 (10)	0.0395 (10)	0.0610 (10)	0.0004 (9)	0.0204 (8)	−0.0017 (8)
C1	0.0605 (11)	0.0397 (10)	0.0534 (10)	−0.0001 (9)	0.0218 (9)	−0.0007 (8)
C6	0.0554 (10)	0.0399 (10)	0.0545 (10)	−0.0027 (9)	0.0240 (8)	−0.0013 (8)
C12	0.0487 (10)	0.0470 (11)	0.0731 (12)	0.0038 (9)	0.0214 (9)	−0.0080 (10)
C11	0.0546 (11)	0.0458 (11)	0.0710 (12)	−0.0044 (9)	0.0238 (9)	−0.0098 (10)
C20	0.0519 (10)	0.0526 (12)	0.0648 (11)	0.0029 (9)	0.0251 (9)	−0.0079 (10)
C9	0.0638 (12)	0.0409 (11)	0.0730 (12)	−0.0069 (10)	0.0176 (10)	−0.0079 (9)
C2	0.0712 (12)	0.0392 (10)	0.0593 (10)	0.0030 (10)	0.0305 (10)	0.0009 (9)
C5	0.0623 (12)	0.0500 (11)	0.0601 (11)	−0.0002 (10)	0.0215 (9)	−0.0089 (9)
C17	0.0510 (11)	0.0743 (15)	0.0850 (15)	0.0001 (11)	0.0207 (11)	−0.0111 (13)
C10	0.0663 (12)	0.0445 (11)	0.0633 (12)	0.0067 (10)	0.0185 (10)	−0.0027 (10)
C3	0.0659 (12)	0.0612 (13)	0.0592 (11)	0.0117 (11)	0.0195 (10)	0.0024 (10)
C18	0.0842 (15)	0.0556 (13)	0.0758 (13)	0.0181 (12)	0.0346 (11)	0.0065 (11)
C21	0.0695 (13)	0.0741 (15)	0.0702 (13)	−0.0071 (12)	0.0318 (11)	−0.0062 (12)
C4	0.0642 (12)	0.0679 (14)	0.0581 (11)	0.0047 (11)	0.0135 (9)	−0.0080 (10)
N2	0.1075 (15)	0.0767 (14)	0.0739 (12)	0.0162 (12)	0.0432 (11)	0.0031 (10)
C13	0.0691 (13)	0.0496 (13)	0.0844 (15)	0.0020 (11)	0.0100 (11)	−0.0020 (11)
C24	0.0709 (14)	0.0604 (14)	0.1057 (19)	0.0073 (12)	0.0118 (13)	−0.0213 (14)
C25	0.0668 (13)	0.0516 (12)	0.0803 (13)	0.0061 (11)	0.0170 (10)	−0.0087 (11)
C14	0.0882 (17)	0.0614 (14)	0.0978 (17)	0.0092 (13)	0.0241 (14)	0.0120 (13)
C23	0.0663 (14)	0.105 (2)	0.0869 (18)	0.0002 (15)	0.0207 (12)	−0.0399 (17)
C22	0.0761 (15)	0.105 (2)	0.0679 (14)	−0.0043 (15)	0.0270 (11)	−0.0103 (14)
C19	0.1040 (18)	0.0717 (15)	0.0895 (16)	0.0167 (14)	0.0460 (14)	−0.0053 (13)
C15	0.0762 (16)	0.093 (2)	0.0865 (17)	0.0249 (16)	0.0158 (13)	0.0133 (15)
C16	0.0588 (13)	0.110 (2)	0.0824 (16)	0.0111 (15)	0.0096 (12)	−0.0049 (16)

Geometric parameters (Å, º) top

O1—C1	1.362 (2)	C17—C16	1.375 (3)
O1—C9	1.426 (2)	C17—H17	0.9300
O2—C11	1.431 (2)	C10—N2	1.137 (2)
O2—N1	1.4748 (19)	C3—C4	1.381 (3)
O3—C2	1.368 (2)	C3—H3	0.9300
O3—C18	1.437 (2)	C18—C19	1.471 (3)
N1—C20	1.438 (2)	C18—H18A	0.9700
N1—C7	1.487 (2)	C18—H18B	0.9700
C7—C6	1.497 (2)	C21—C22	1.381 (3)
C7—C8	1.529 (2)	C21—H21	0.9300
C7—H7	0.9800	C4—H4	0.9300
C8—C10	1.473 (3)	C13—C14	1.371 (3)
C8—C9	1.526 (3)	C13—H13	0.9300
C8—C11	1.561 (3)	C24—C23	1.383 (4)
C1—C6	1.395 (2)	C24—C25	1.386 (3)
C1—C2	1.403 (3)	C24—H24	0.9300
C6—C5	1.394 (2)	C25—H25	0.9300
C12—C17	1.380 (3)	C14—C15	1.376 (3)
C12—C13	1.388 (3)	C14—H14	0.9300
C12—C11	1.502 (3)	C23—C22	1.371 (4)
C11—H11	0.9800	C23—H23	0.9300
C20—C21	1.378 (3)	C22—H22	0.9300
C20—C25	1.389 (3)	C19—H19A	0.9600
C9—H9A	0.9700	C19—H19B	0.9600
C9—H9B	0.9700	C19—H19C	0.9600
C2—C3	1.370 (3)	C15—C16	1.354 (4)
C5—C4	1.365 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300

C1—O1—C9	114.04 (14)	C16—C17—H17	119.7
C11—O2—N1	103.20 (12)	C12—C17—H17	119.7
C2—O3—C18	117.52 (16)	N2—C10—C8	176.6 (2)
C20—N1—O2	106.84 (13)	C2—C3—C4	120.16 (19)
C20—N1—C7	114.86 (14)	C2—C3—H3	119.9
O2—N1—C7	99.47 (12)	C4—C3—H3	119.9
N1—C7—C6	114.78 (14)	O3—C18—C19	108.52 (18)
N1—C7—C8	99.30 (13)	O3—C18—H18A	110.0
C6—C7—C8	112.86 (14)	C19—C18—H18A	110.0
N1—C7—H7	109.8	O3—C18—H18B	110.0
C6—C7—H7	109.8	C19—C18—H18B	110.0
C8—C7—H7	109.8	H18A—C18—H18B	108.4
C10—C8—C9	109.21 (15)	C20—C21—C22	120.2 (2)
C10—C8—C7	111.77 (15)	C20—C21—H21	119.9
C9—C8—C7	107.33 (15)	C22—C21—H21	119.9
C10—C8—C11	114.76 (15)	C5—C4—C3	120.78 (19)
C9—C8—C11	110.76 (15)	C5—C4—H4	119.6
C7—C8—C11	102.66 (14)	C3—C4—H4	119.6
O1—C1—C6	122.82 (16)	C14—C13—C12	120.3 (2)
O1—C1—C2	117.10 (16)	C14—C13—H13	119.8
C6—C1—C2	119.98 (17)	C12—C13—H13	119.8
C5—C6—C1	118.78 (17)	C23—C24—C25	120.0 (2)
C5—C6—C7	120.29 (16)	C23—C24—H24	120.0
C1—C6—C7	120.58 (16)	C25—C24—H24	120.0
C17—C12—C13	118.5 (2)	C24—C25—C20	119.1 (2)
C17—C12—C11	120.17 (19)	C24—C25—H25	120.4
C13—C12—C11	121.32 (18)	C20—C25—H25	120.4
O2—C11—C12	109.16 (15)	C13—C14—C15	120.2 (2)
O2—C11—C8	104.61 (14)	C13—C14—H14	119.9
C12—C11—C8	116.01 (15)	C15—C14—H14	119.9
O2—C11—H11	108.9	C22—C23—C24	120.5 (2)
C12—C11—H11	108.9	C22—C23—H23	119.7
C8—C11—H11	108.9	C24—C23—H23	119.7
C21—C20—C25	120.29 (19)	C23—C22—C21	119.7 (2)
C21—C20—N1	117.04 (18)	C23—C22—H22	120.1
C25—C20—N1	122.65 (18)	C21—C22—H22	120.1
O1—C9—C8	111.13 (15)	C18—C19—H19A	109.5
O1—C9—H9A	109.4	C18—C19—H19B	109.5
C8—C9—H9A	109.4	H19A—C19—H19B	109.5
O1—C9—H9B	109.4	C18—C19—H19C	109.5
C8—C9—H9B	109.4	H19A—C19—H19C	109.5
H9A—C9—H9B	108.0	H19B—C19—H19C	109.5
O3—C2—C3	124.70 (18)	C16—C15—C14	119.9 (2)
O3—C2—C1	115.63 (17)	C16—C15—H15	120.0
C3—C2—C1	119.67 (17)	C14—C15—H15	120.0
C4—C5—C6	120.53 (18)	C15—C16—C17	120.5 (2)
C4—C5—H5	119.7	C15—C16—H16	119.7
C6—C5—H5	119.7	C17—C16—H16	119.7
C16—C17—C12	120.6 (2)

C11—O2—N1—C20	−172.76 (14)	O2—N1—C20—C25	40.8 (2)
C11—O2—N1—C7	−53.05 (15)	C7—N1—C20—C25	−68.5 (2)
C20—N1—C7—C6	−73.56 (19)	C1—O1—C9—C8	−54.2 (2)
O2—N1—C7—C6	172.81 (13)	C10—C8—C9—O1	−57.5 (2)
C20—N1—C7—C8	165.83 (15)	C7—C8—C9—O1	63.88 (19)
O2—N1—C7—C8	52.20 (14)	C11—C8—C9—O1	175.21 (14)
N1—C7—C8—C10	−156.53 (15)	C18—O3—C2—C3	10.7 (3)
C6—C7—C8—C10	81.46 (18)	C18—O3—C2—C1	−168.42 (16)
N1—C7—C8—C9	83.74 (16)	O1—C1—C2—O3	−1.0 (2)
C6—C7—C8—C9	−38.3 (2)	C6—C1—C2—O3	175.48 (15)
N1—C7—C8—C11	−33.04 (16)	O1—C1—C2—C3	179.81 (16)
C6—C7—C8—C11	−155.05 (14)	C6—C1—C2—C3	−3.7 (3)
C9—O1—C1—C6	18.2 (2)	C1—C6—C5—C4	−1.1 (3)
C9—O1—C1—C2	−165.40 (15)	C7—C6—C5—C4	172.18 (17)
O1—C1—C6—C5	179.70 (16)	C13—C12—C17—C16	0.3 (3)
C2—C1—C6—C5	3.4 (3)	C11—C12—C17—C16	178.19 (19)
O1—C1—C6—C7	6.5 (3)	O3—C2—C3—C4	−177.50 (18)
C2—C1—C6—C7	−169.83 (15)	C1—C2—C3—C4	1.6 (3)
N1—C7—C6—C5	80.0 (2)	C2—O3—C18—C19	164.34 (17)
C8—C7—C6—C5	−167.23 (16)	C25—C20—C21—C22	−0.7 (3)
N1—C7—C6—C1	−106.92 (18)	N1—C20—C21—C22	−179.33 (18)
C8—C7—C6—C1	5.9 (2)	C6—C5—C4—C3	−1.0 (3)
N1—O2—C11—C12	155.50 (14)	C2—C3—C4—C5	0.8 (3)
N1—O2—C11—C8	30.73 (17)	C17—C12—C13—C14	−0.4 (3)
C17—C12—C11—O2	137.73 (18)	C11—C12—C13—C14	−178.3 (2)
C13—C12—C11—O2	−44.4 (2)	C23—C24—C25—C20	−1.2 (3)
C17—C12—C11—C8	−104.5 (2)	C21—C20—C25—C24	2.0 (3)
C13—C12—C11—C8	73.4 (2)	N1—C20—C25—C24	−179.50 (18)
C10—C8—C11—O2	123.37 (17)	C12—C13—C14—C15	−0.2 (4)
C9—C8—C11—O2	−112.41 (17)	C25—C24—C23—C22	−0.7 (4)
C7—C8—C11—O2	1.90 (18)	C24—C23—C22—C21	2.0 (4)
C10—C8—C11—C12	3.1 (2)	C20—C21—C22—C23	−1.3 (3)
C9—C8—C11—C12	127.29 (17)	C13—C14—C15—C16	1.0 (4)
C7—C8—C11—C12	−118.40 (17)	C14—C15—C16—C17	−1.1 (4)
O2—N1—C20—C21	−140.65 (17)	C12—C17—C16—C15	0.5 (3)
C7—N1—C20—C21	110.10 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···N1	0.97	2.64	2.960 (2)	100
C25—H25···O1ⁱ	0.93	2.89	3.748 (3)	154
C23—H23···N2ⁱⁱ	0.93	2.79	3.443 (3)	128

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂N₂O₃
M_r	398.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.2994 (9), 7.5421 (5), 18.7248 (12)
β (°)	107.596 (4)
V (Å³)	2059.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18432, 5109, 2805
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.164, 1.04
No. of reflections	5109
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···N1	0.97	2.64	2.960 (2)	99.7
C25—H25···O1ⁱ	0.93	2.89	3.748 (3)	154.2
C23—H23···N2ⁱⁱ	0.93	2.79	3.443 (3)	128.0

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

Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797. CSD CrossRef Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., 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
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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., Srinivasan, J. & Bakthadoss, M. (2012). Acta Cryst. E68, o283–o284. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Winn, M., Arendsen, D., Dodge, P., Dren, A., Dunnigan, D., Hallas, R., Hwang, K., Kyncl, J., Lee, Y. H., Plotnikoff, N., Young Zaugg, H., Dalzell, H. & Razdan, R. K. (1976). J. Med. Chem. 19, 461–471. CrossRef CAS PubMed Web of Science Google Scholar

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Volume 68| Part 6| June 2012| Page o1660

doi:10.1107/S160053681201906X

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

rac-6-Eth­­oxy-3,3a,4,9b-tetra­hydro-1,3-di­phenyl-1H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-6-Ethoxy-3,3a,4,9b-tetrahydro-1,3-diphenyl-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile