Methyl 6-eth­oxy-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-car­boxylate

Suresh, G.; Srinivasan, J.; Bakthadoss, M.; Aravindhan, S.

doi:10.1107/S1600536812051720

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o180

doi:10.1107/S1600536812051720

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Methyl 6-ethoxy-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carboxylate

G. Suresh,^a J. Srinivasan,^b M. Bakthadoss ^b and S. Aravindhan ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
^*Correspondence e-mail: aravindhanpresidency@gmail.com

(Received 16 December 2012; accepted 22 December 2012; online 4 January 2013)

In the title compound, C₂₀H₁₉NO₅, the dihedral angle between the mean plane of the pyran ring (which has a half-chair conformation) and the benzene ring of the chromeno ring system is 7.21 (7)°. The dihedral angle between the mean plane of the chromeno ring system and the isoxazole ring is 21.78 (6)°, while the isoxazole ring forms a dihedral angle of 72.60 (8)° with the attached phenyl ring. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R²₂(10) ring motif. These dimers are linked via C—H⋯N hydrogen bonds, forming chains along [001].

Related literature

For the biological activity of chromenopyrroles, see: Caine (1993 ), and of benzopyran and isoxazolidine derivatives, see: Lin et al. (1996 ); Hu et al. (2004 ). For uses of isoxazole derivatives, see: Baraldi et al. (1987 ); Eddington et al. (2002 ). For related structures, see: Gangadharan et al. (2011 ); Swaminathan et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₉NO₅
M_r = 353.36
Monoclinic, P 2₁ /c
a = 12.9342 (6) Å
b = 7.5591 (2) Å
c = 18.7138 (8) Å
β = 105.440 (2)°
V = 1763.63 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.976, T_max = 0.990
13064 measured reflections
4245 independent reflections
3253 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.125
S = 1.03
4245 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O4ⁱ	0.97	2.55	3.3875 (19)	145
C8—H8⋯N1ⁱⁱ	0.98	2.52	3.4269 (19)	154
Symmetry codes: (i) -x, -y+2, -z+2; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051720/su2543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051720/su2543Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051720/su2543Isup3.cml

checkCIF report

Comment top

Chromenopyrrole compounds are used in the treatment of impulsive disorders (Caine, 1993). It is well known that benzo-pyran and isoxazolidine derivatives possess interesting biological and pharmacological activities (Lin et al., 1996; Hu et al., 2004). Isoxazole and its derivatives 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). Herein we report on the synthesis and the crystal structure of the new title chromeno compound.

The molecular structure of the title molecule is illustrated in Fig. 1. In the chromeno ring system the pyran ring has a half chair conformation. Its mean plane makes a dihedral angle with the benzene ring of 7.21 (7)°. The dihedral angle between the mean plane of the chromeno ring system (fusion of benzene and pyran rings) and the isoxazole ring (O2/N1/C7-C9) is 21.78 (6)°. The isoxazole ring also forms a dihedral angle of 72.60 (8)° with the phenyl ring (C15—C20). The geometric parameters of the title molecule agree well with those reported for closely related structures (Gangadharan et al., 2011; Swaminathan et al., 2011).

In the crystal, molecules are linked via pairs of C-H···O hydrogen bonds to form inversion dimers with an R²₂(10) ring motif (Bernstein et al., 1995; Table 1 and Fig. 2). These dimers are linked via C-H···N hydrogen bonds to form chains along the c axis.

Related literature top

For the biological activity of chromenopyrroles, see: Caine (1993), and of benzopyran and isoxazolidine derivatives, see: Lin et al. (1996); Hu et al. (2004). For uses of isoxazole derivatives, see: Baraldi et al. (1987); Eddington et al. (2002). For related structures, see: Gangadharan et al. (2011); Swaminathan et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

At 283 - 293 K, NCS (4 mmol) was added pinch wise over 3 h to a solution of ((E)-methyl2-((2ethoxy-6-((E)-(hydroxyimino)methyl)phenoxy)methyl) -3-phenylacrylate (2 mmol) in CCl₄. After Et₃N (4 mmol) was added to the reaction mixture which was stirred at room temperature for 2 h. After completion of the reaction, the mixture was evaporated under reduced pressure and the resulting crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 × 15 ml). The combined organic layers were washed with brine (2 × 10 ml) and dried over anhydrous Na₂SO₄. The organic layer was evaporated and purified by column chromatography (silica gel 60–120 mesh 7% EtOAc in hexanes) to provide the desired pure title product as a colourless solid. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution in ethyl acetate.

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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound. The C-H···O and C-H···N hydrogen bonds are shown as dashed lines (see Table 1 for details).

Methyl 6-ethoxy-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a- carboxylate top

Crystal data top

C₂₀H₁₉NO₅	F(000) = 744
M_r = 353.36	D_x = 1.331 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4245 reflections
a = 12.9342 (6) Å	θ = 2.3–28.4°
b = 7.5591 (2) Å	µ = 0.10 mm⁻¹
c = 18.7138 (8) Å	T = 298 K
β = 105.440 (2)°	Monoclinic, colourless
V = 1763.63 (12) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4245 independent reflections
Radiation source: fine-focus sealed tube	3253 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→17
T_min = 0.976, T_max = 0.990	k = −9→6
13064 measured reflections	l = −24→25

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) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0578P)² + 0.5069P] where P = (F_o² + 2F_c²)/3
4245 reflections	(Δ/σ)_max = 0.002
237 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₁₉NO₅	V = 1763.63 (12) Å³
M_r = 353.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9342 (6) Å	µ = 0.10 mm⁻¹
b = 7.5591 (2) Å	T = 298 K
c = 18.7138 (8) Å	0.25 × 0.20 × 0.10 mm
β = 105.440 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4245 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3253 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.990	R_int = 0.017
13064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
4245 reflections	Δρ_min = −0.22 e Å⁻³
237 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	0.34469 (12)	0.7365 (2)	0.84801 (8)	0.0408 (3)
H1	0.3280	0.7202	0.7969	0.049*
C2	0.44803 (13)	0.7149 (2)	0.89052 (9)	0.0497 (4)
H2	0.5013	0.6828	0.8680	0.060*
C3	0.47417 (12)	0.7405 (2)	0.96675 (9)	0.0467 (4)
H3	0.5449	0.7270	0.9945	0.056*
C4	0.39633 (11)	0.78572 (19)	1.00188 (8)	0.0365 (3)
C5	0.28961 (10)	0.80410 (17)	0.95890 (7)	0.0299 (3)
C6	0.10418 (10)	0.81790 (19)	0.95728 (7)	0.0331 (3)
H6A	0.0582	0.8683	0.9853	0.040*
H6B	0.0895	0.6921	0.9516	0.040*
C7	0.08137 (10)	0.90610 (17)	0.88085 (7)	0.0290 (3)
C8	−0.02921 (11)	0.87517 (19)	0.82484 (7)	0.0341 (3)
H8	−0.0613	0.9908	0.8088	0.041*
C9	0.15362 (10)	0.81458 (16)	0.84177 (7)	0.0291 (3)
C10	0.26470 (11)	0.78305 (17)	0.88215 (7)	0.0308 (3)
C11	0.51955 (13)	0.7982 (3)	1.12204 (9)	0.0539 (4)
H11A	0.5661	0.8839	1.1076	0.065*
H11B	0.5473	0.6806	1.1177	0.065*
C12	0.51486 (19)	0.8317 (4)	1.20010 (11)	0.0856 (7)
H12A	0.4827	0.9451	1.2029	0.128*
H12B	0.5862	0.8302	1.2326	0.128*
H12C	0.4727	0.7413	1.2149	0.128*
C13	0.10049 (11)	1.10449 (19)	0.89314 (7)	0.0338 (3)
C14	0.20504 (14)	1.3490 (2)	0.87993 (12)	0.0608 (5)
H14A	0.1388	1.4113	0.8606	0.091*
H14B	0.2550	1.3815	0.8524	0.091*
H14C	0.2342	1.3792	0.9312	0.091*
C15	−0.10961 (10)	0.76672 (18)	0.85102 (7)	0.0331 (3)
C16	−0.18456 (12)	0.8534 (2)	0.87901 (9)	0.0437 (4)
H16	−0.1854	0.9764	0.8802	0.052*
C17	−0.25822 (14)	0.7588 (3)	0.90523 (10)	0.0565 (4)
H17	−0.3079	0.8180	0.9244	0.068*
C18	−0.25809 (14)	0.5775 (3)	0.90297 (10)	0.0565 (4)
H18	−0.3081	0.5139	0.9202	0.068*
C19	−0.18410 (14)	0.4897 (2)	0.87527 (10)	0.0550 (4)
H19	−0.1840	0.3667	0.8740	0.066*
C20	−0.10973 (13)	0.5836 (2)	0.84930 (9)	0.0452 (4)
H20	−0.0598	0.5236	0.8307	0.054*
N1	0.10693 (10)	0.75033 (17)	0.77828 (6)	0.0376 (3)
O1	0.21512 (7)	0.84634 (13)	0.99612 (5)	0.0351 (2)
O2	−0.00309 (9)	0.79042 (16)	0.76155 (5)	0.0456 (3)
O3	0.41260 (8)	0.81419 (16)	1.07581 (6)	0.0473 (3)
O4	0.04263 (10)	1.19594 (15)	0.91752 (7)	0.0560 (3)
O5	0.18555 (8)	1.16068 (13)	0.87330 (6)	0.0442 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (8)	0.0401 (8)	0.0440 (7)	0.0001 (6)	0.0196 (6)	−0.0057 (6)
C2	0.0400 (8)	0.0554 (10)	0.0602 (10)	0.0050 (7)	0.0244 (7)	−0.0042 (8)
C3	0.0295 (7)	0.0533 (10)	0.0561 (9)	0.0037 (6)	0.0093 (6)	0.0042 (7)
C4	0.0342 (7)	0.0344 (8)	0.0398 (7)	−0.0005 (5)	0.0081 (6)	0.0035 (6)
C5	0.0305 (6)	0.0247 (6)	0.0359 (6)	0.0000 (5)	0.0110 (5)	0.0013 (5)
C6	0.0304 (6)	0.0377 (7)	0.0326 (6)	0.0001 (5)	0.0106 (5)	0.0037 (5)
C7	0.0292 (6)	0.0276 (7)	0.0306 (6)	−0.0009 (5)	0.0087 (5)	0.0015 (5)
C8	0.0335 (7)	0.0340 (7)	0.0331 (6)	−0.0002 (5)	0.0057 (5)	0.0031 (5)
C9	0.0353 (7)	0.0228 (6)	0.0312 (6)	−0.0029 (5)	0.0125 (5)	0.0008 (5)
C10	0.0343 (7)	0.0228 (6)	0.0368 (6)	−0.0021 (5)	0.0121 (5)	−0.0019 (5)
C11	0.0421 (9)	0.0584 (11)	0.0511 (9)	−0.0016 (7)	−0.0051 (7)	0.0071 (8)
C12	0.0797 (15)	0.118 (2)	0.0469 (10)	−0.0033 (14)	−0.0051 (10)	0.0057 (12)
C13	0.0363 (7)	0.0312 (7)	0.0323 (6)	0.0019 (5)	0.0062 (5)	−0.0006 (5)
C14	0.0486 (10)	0.0267 (8)	0.0982 (14)	−0.0065 (7)	0.0038 (9)	0.0070 (8)
C15	0.0287 (6)	0.0345 (7)	0.0333 (6)	−0.0011 (5)	0.0033 (5)	0.0003 (5)
C16	0.0376 (8)	0.0377 (8)	0.0557 (9)	−0.0017 (6)	0.0124 (7)	−0.0071 (7)
C17	0.0406 (9)	0.0671 (12)	0.0677 (11)	−0.0065 (8)	0.0247 (8)	−0.0119 (9)
C18	0.0463 (9)	0.0633 (12)	0.0616 (10)	−0.0185 (8)	0.0177 (8)	0.0046 (9)
C19	0.0575 (10)	0.0367 (9)	0.0691 (11)	−0.0102 (7)	0.0139 (9)	0.0050 (8)
C20	0.0449 (8)	0.0344 (8)	0.0581 (9)	0.0015 (6)	0.0168 (7)	−0.0015 (7)
N1	0.0399 (7)	0.0405 (7)	0.0332 (5)	−0.0065 (5)	0.0112 (5)	−0.0032 (5)
O1	0.0313 (5)	0.0444 (6)	0.0297 (4)	0.0024 (4)	0.0082 (4)	−0.0010 (4)
O2	0.0386 (5)	0.0654 (7)	0.0316 (5)	−0.0081 (5)	0.0073 (4)	−0.0052 (5)
O3	0.0377 (6)	0.0623 (7)	0.0381 (5)	0.0015 (5)	0.0036 (4)	0.0023 (5)
O4	0.0714 (8)	0.0398 (6)	0.0659 (7)	0.0076 (6)	0.0343 (6)	−0.0079 (5)
O5	0.0364 (5)	0.0245 (5)	0.0706 (7)	−0.0013 (4)	0.0123 (5)	0.0041 (4)

Geometric parameters (Å, º) top

C1—C2	1.371 (2)	C11—C12	1.500 (3)
C1—C10	1.3980 (19)	C11—H11A	0.9700
C1—H1	0.9300	C11—H11B	0.9700
C2—C3	1.389 (2)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.384 (2)	C12—H12C	0.9600
C3—H3	0.9300	C13—O4	1.1949 (17)
C4—O3	1.3600 (17)	C13—O5	1.3215 (17)
C4—C5	1.4073 (18)	C14—O5	1.4451 (19)
C5—O1	1.3685 (16)	C14—H14A	0.9600
C5—C10	1.3948 (18)	C14—H14B	0.9600
C6—O1	1.4416 (16)	C14—H14C	0.9600
C6—C7	1.5337 (17)	C15—C16	1.383 (2)
C6—H6A	0.9700	C15—C20	1.385 (2)
C6—H6B	0.9700	C16—C17	1.382 (2)
C7—C9	1.5003 (18)	C16—H16	0.9300
C7—C13	1.5273 (19)	C17—C18	1.371 (3)
C7—C8	1.5494 (17)	C17—H17	0.9300
C8—O2	1.4630 (17)	C18—C19	1.375 (3)
C8—C15	1.5049 (19)	C18—H18	0.9300
C8—H8	0.9800	C19—C20	1.384 (2)
C9—N1	1.2767 (17)	C19—H19	0.9300
C9—C10	1.4540 (18)	C20—H20	0.9300
C11—O3	1.4281 (18)	N1—O2	1.4063 (16)

C2—C1—C10	119.37 (14)	O3—C11—H11B	110.3
C2—C1—H1	120.3	C12—C11—H11B	110.3
C10—C1—H1	120.3	H11A—C11—H11B	108.6
C1—C2—C3	120.84 (14)	C11—C12—H12A	109.5
C1—C2—H2	119.6	C11—C12—H12B	109.5
C3—C2—H2	119.6	H12A—C12—H12B	109.5
C4—C3—C2	120.88 (14)	C11—C12—H12C	109.5
C4—C3—H3	119.6	H12A—C12—H12C	109.5
C2—C3—H3	119.6	H12B—C12—H12C	109.5
O3—C4—C3	125.96 (13)	O4—C13—O5	125.05 (14)
O3—C4—C5	115.37 (12)	O4—C13—C7	122.19 (13)
C3—C4—C5	118.67 (13)	O5—C13—C7	112.76 (11)
O1—C5—C10	123.36 (12)	O5—C14—H14A	109.5
O1—C5—C4	116.64 (11)	O5—C14—H14B	109.5
C10—C5—C4	119.98 (12)	H14A—C14—H14B	109.5
O1—C6—C7	108.90 (10)	O5—C14—H14C	109.5
O1—C6—H6A	109.9	H14A—C14—H14C	109.5
C7—C6—H6A	109.9	H14B—C14—H14C	109.5
O1—C6—H6B	109.9	C16—C15—C20	119.08 (14)
C7—C6—H6B	109.9	C16—C15—C8	118.66 (13)
H6A—C6—H6B	108.3	C20—C15—C8	122.25 (13)
C9—C7—C13	115.42 (11)	C17—C16—C15	120.52 (15)
C9—C7—C6	105.31 (10)	C17—C16—H16	119.7
C13—C7—C6	107.65 (11)	C15—C16—H16	119.7
C9—C7—C8	100.56 (10)	C18—C17—C16	120.00 (16)
C13—C7—C8	109.47 (10)	C18—C17—H17	120.0
C6—C7—C8	118.62 (11)	C16—C17—H17	120.0
O2—C8—C15	110.70 (11)	C17—C18—C19	120.09 (16)
O2—C8—C7	104.08 (10)	C17—C18—H18	120.0
C15—C8—C7	117.10 (10)	C19—C18—H18	120.0
O2—C8—H8	108.2	C18—C19—C20	120.22 (16)
C15—C8—H8	108.2	C18—C19—H19	119.9
C7—C8—H8	108.2	C20—C19—H19	119.9
N1—C9—C10	125.34 (12)	C19—C20—C15	120.09 (15)
N1—C9—C7	115.30 (12)	C19—C20—H20	120.0
C10—C9—C7	118.67 (11)	C15—C20—H20	120.0
C5—C10—C1	120.21 (13)	C9—N1—O2	108.97 (11)
C5—C10—C9	116.22 (11)	C5—O1—C6	116.72 (10)
C1—C10—C9	123.56 (12)	N1—O2—C8	110.62 (9)
O3—C11—C12	106.98 (16)	C4—O3—C11	117.75 (12)
O3—C11—H11A	110.3	C13—O5—C14	115.58 (13)
C12—C11—H11A	110.3

C10—C1—C2—C3	−0.6 (2)	C7—C9—C10—C1	−165.09 (13)
C1—C2—C3—C4	1.0 (3)	C9—C7—C13—O4	173.18 (13)
C2—C3—C4—O3	−179.88 (15)	C6—C7—C13—O4	−69.56 (16)
C2—C3—C4—C5	0.5 (2)	C8—C7—C13—O4	60.65 (17)
O3—C4—C5—O1	−0.61 (18)	C9—C7—C13—O5	−6.14 (16)
C3—C4—C5—O1	179.04 (13)	C6—C7—C13—O5	111.12 (12)
O3—C4—C5—C10	178.04 (12)	C8—C7—C13—O5	−118.67 (12)
C3—C4—C5—C10	−2.3 (2)	O2—C8—C15—C16	−146.00 (12)
O1—C6—C7—C9	61.42 (13)	C7—C8—C15—C16	94.96 (15)
O1—C6—C7—C13	−62.23 (13)	O2—C8—C15—C20	35.24 (17)
O1—C6—C7—C8	172.88 (11)	C7—C8—C15—C20	−83.80 (17)
C9—C7—C8—O2	−5.46 (12)	C20—C15—C16—C17	0.3 (2)
C13—C7—C8—O2	116.48 (12)	C8—C15—C16—C17	−178.49 (14)
C6—C7—C8—O2	−119.52 (12)	C15—C16—C17—C18	−0.6 (3)
C9—C7—C8—C15	117.06 (12)	C16—C17—C18—C19	0.6 (3)
C13—C7—C8—C15	−121.00 (13)	C17—C18—C19—C20	−0.2 (3)
C6—C7—C8—C15	3.00 (18)	C18—C19—C20—C15	−0.1 (2)
C13—C7—C9—N1	−115.20 (13)	C16—C15—C20—C19	0.0 (2)
C6—C7—C9—N1	126.23 (12)	C8—C15—C20—C19	178.80 (13)
C8—C7—C9—N1	2.45 (15)	C10—C9—N1—O2	172.22 (12)
C13—C7—C9—C10	73.79 (14)	C7—C9—N1—O2	1.90 (16)
C6—C7—C9—C10	−44.78 (15)	C10—C5—O1—C6	18.01 (17)
C8—C7—C9—C10	−168.57 (11)	C4—C5—O1—C6	−163.39 (12)
O1—C5—C10—C1	−178.77 (13)	C7—C6—O1—C5	−50.96 (15)
C4—C5—C10—C1	2.7 (2)	C9—N1—O2—C8	−5.87 (15)
O1—C5—C10—C9	2.05 (18)	C15—C8—O2—N1	−119.54 (12)
C4—C5—C10—C9	−176.51 (12)	C7—C8—O2—N1	7.10 (14)
C2—C1—C10—C5	−1.2 (2)	C3—C4—O3—C11	0.7 (2)
C2—C1—C10—C9	177.92 (14)	C5—C4—O3—C11	−179.68 (13)
N1—C9—C10—C5	−155.97 (13)	C12—C11—O3—C4	−178.77 (16)
C7—C9—C10—C5	14.06 (17)	O4—C13—O5—C14	−2.3 (2)
N1—C9—C10—C1	24.9 (2)	C7—C13—O5—C14	176.95 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O4ⁱ	0.97	2.55	3.3875 (19)	145
C8—H8···N1ⁱⁱ	0.98	2.52	3.4269 (19)	154

Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉NO₅
M_r	353.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.9342 (6), 7.5591 (2), 18.7138 (8)
β (°)	105.440 (2)
V (Å³)	1763.63 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.976, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	13064, 4245, 3253
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.125, 1.03
No. of reflections	4245
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.22

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O4ⁱ	0.97	2.55	3.3875 (19)	145
C8—H8···N1ⁱⁱ	0.98	2.52	3.4269 (19)	154

Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, y+1/2, −z+3/2.

Acknowledgements

GS and SA thank the UGC, India, for financial support and GS thanks the SAIF, IIT-Madras, for the instrumentation facility.

References

Baraldi, P. G., Barco, A., Benetti, S., Pollini, G. P. & Simoni, D. (1987). Synthesis, pp. 857–869. CrossRef Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 6-eth­­oxy-3-phenyl-3a,4-di­hydro-3H-chromeno[4,3-c]isoxazole-3a-car­boxylate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 6-ethoxy-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carboxylate