rac-Methyl 3-(2-meth-oxy-phen-yl)-3a,4-di-hydro-3H-chromeno[4,3-c]isoxazole-3a-carboxyl-ate.

The title compound, C19H17NO5, comprising two stereogenic C atoms of the same configuration, crystallizes in a centrosymmetric space group as a racemate. The pyran ring adopts a half-chair conformation, while the isoxazole ring adopts an envelope conformation with the C atom bonded to the meth-oxy-phenyl group as the flap. The dihedral angle between the mean plane of the pyran ring and the adjacent benzene ring is 5.86 (5)°. In the crystal, mol-ecules are linked by a weak C-H⋯O hydrogen bond, forming a chain along the a axis.

Related literature

For the biological activity of isoxazole and benzpyran derivatives, see: Winn et al. (1976 ▶); Rozman et al. (2002 ▶); Caine (1993 ▶). For conformational analysis and puckering parameters, see: Cremer & Pople, (1975 ▶). For a related structure, see: Paramasivam et al. (2012 ▶).

Experimental

Crystal data

C19H17NO5

M = 339.34

Triclinic,

a = 9.4804 (4) Å

b = 9.6401 (4) Å

c = 10.7013 (5) Å

α = 81.308 (2)°

β = 67.801 (2)°

γ = 69.085 (2)°

V = 845.71 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.971, T max = 0.981

12631 measured reflections

3462 independent reflections

3012 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 1.04

3462 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 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 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008635/is5259sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008635/is5259Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008635/is5259Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H17NO5	Z = 2
Mr = 339.34	F(000) = 356
Triclinic, P1	Triclinic
Hall symbol: -P 1	Dx = 1.333 Mg m−3
a = 9.4804 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6401 (4) Å	Cell parameters from 3462 reflections
c = 10.7013 (5) Å	θ = 2.1–26.4°
α = 81.308 (2)°	µ = 0.10 mm−1
β = 67.801 (2)°	T = 298 K
γ = 69.085 (2)°	Block, colourless
V = 845.71 (6) Å3	0.30 × 0.25 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	3462 independent reflections
Radiation source: fine-focus sealed tube	3012 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.971, Tmax = 0.981	k = −11→12
12631 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.182P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3462 reflections	Δρmax = 0.22 e Å−3
229 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.093 (6)

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.

	x	y	z	Uiso*/Ueq
C1	0.76808 (16)	0.07314 (16)	0.63411 (13)	0.0495 (3)
C2	0.7901 (2)	−0.0399 (2)	0.55433 (17)	0.0684 (5)
H2	0.8490	−0.1376	0.5680	0.082*
C3	0.7231 (2)	−0.0043 (3)	0.4548 (2)	0.0868 (7)
H3	0.7355	−0.0791	0.4021	0.104*
C4	0.6378 (3)	0.1410 (3)	0.4322 (2)	0.0881 (6)
H4	0.5961	0.1633	0.3630	0.106*
C5	0.6143 (2)	0.2526 (2)	0.51121 (16)	0.0660 (4)
H5	0.5564	0.3500	0.4957	0.079*
C6	0.67764 (16)	0.21950 (16)	0.61527 (13)	0.0471 (3)
C7	0.65159 (14)	0.32946 (14)	0.70800 (12)	0.0408 (3)
C8	0.70310 (13)	0.27662 (13)	0.82869 (12)	0.0364 (3)
C9	0.86085 (15)	0.14797 (14)	0.78248 (14)	0.0441 (3)
H9A	0.9423	0.1821	0.7119	0.053*
H9B	0.8986	0.1103	0.8575	0.053*
C10	0.57037 (15)	0.22930 (13)	0.94184 (12)	0.0402 (3)
C11	0.5050 (2)	0.09585 (19)	1.14593 (15)	0.0660 (4)
H11A	0.4436	0.1773	1.2068	0.099*
H11B	0.5573	0.0116	1.1917	0.099*
H11C	0.4343	0.0707	1.1153	0.099*
C12	0.70663 (14)	0.42463 (13)	0.86467 (12)	0.0385 (3)
H12	0.6616	0.4354	0.9629	0.046*
C13	0.87197 (14)	0.44101 (14)	0.81075 (13)	0.0410 (3)
C14	0.92427 (19)	0.51937 (18)	0.69297 (15)	0.0559 (4)
H14	0.8557	0.5657	0.6447	0.067*
C15	1.0783 (2)	0.5294 (2)	0.64626 (18)	0.0781 (5)
H15	1.1132	0.5817	0.5667	0.094*
C16	1.1786 (2)	0.4619 (3)	0.7180 (2)	0.0845 (6)
H16	1.2815	0.4692	0.6866	0.101*
C17	1.12966 (19)	0.3833 (2)	0.8361 (2)	0.0708 (5)
H17	1.1990	0.3378	0.8837	0.085*
C18	0.97535 (16)	0.37288 (15)	0.88296 (15)	0.0493 (3)
C19	1.0138 (3)	0.2223 (2)	1.0745 (2)	0.0877 (6)
H19A	1.1042	0.1442	1.0219	0.132*
H19B	0.9531	0.1807	1.1551	0.132*
H19C	1.0517	0.2909	1.0983	0.132*
N1	0.59522 (14)	0.47046 (13)	0.69528 (12)	0.0500 (3)
O1	0.83574 (12)	0.03193 (10)	0.73258 (10)	0.0533 (3)
O2	0.59926 (11)	0.53548 (10)	0.80421 (10)	0.0503 (3)
O3	0.43272 (12)	0.27371 (14)	0.94996 (11)	0.0638 (3)
O4	0.62574 (12)	0.13826 (11)	1.03084 (10)	0.0543 (3)
O5	0.91320 (14)	0.29842 (12)	0.99727 (11)	0.0631 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0439 (7)	0.0600 (8)	0.0443 (7)	−0.0261 (6)	−0.0036 (6)	−0.0086 (6)
C2	0.0591 (9)	0.0735 (10)	0.0691 (10)	−0.0301 (8)	−0.0017 (8)	−0.0262 (8)
C3	0.0716 (12)	0.1236 (18)	0.0755 (12)	−0.0442 (13)	−0.0075 (10)	−0.0495 (12)
C4	0.0765 (13)	0.137 (2)	0.0656 (11)	−0.0388 (13)	−0.0267 (10)	−0.0296 (12)
C5	0.0616 (10)	0.0929 (12)	0.0524 (8)	−0.0310 (9)	−0.0235 (7)	−0.0032 (8)
C6	0.0423 (7)	0.0615 (8)	0.0412 (6)	−0.0252 (6)	−0.0105 (5)	−0.0016 (6)
C7	0.0331 (6)	0.0483 (7)	0.0433 (6)	−0.0173 (5)	−0.0140 (5)	0.0041 (5)
C8	0.0310 (6)	0.0381 (6)	0.0404 (6)	−0.0124 (5)	−0.0122 (5)	0.0005 (5)
C9	0.0371 (6)	0.0408 (6)	0.0520 (7)	−0.0090 (5)	−0.0155 (5)	−0.0037 (5)
C10	0.0419 (7)	0.0419 (6)	0.0416 (6)	−0.0195 (5)	−0.0139 (5)	−0.0018 (5)
C11	0.0900 (12)	0.0707 (10)	0.0456 (8)	−0.0495 (9)	−0.0156 (8)	0.0110 (7)
C12	0.0333 (6)	0.0377 (6)	0.0448 (6)	−0.0116 (5)	−0.0146 (5)	0.0010 (5)
C13	0.0363 (6)	0.0436 (6)	0.0462 (6)	−0.0167 (5)	−0.0138 (5)	−0.0025 (5)
C14	0.0581 (9)	0.0685 (9)	0.0499 (7)	−0.0350 (7)	−0.0172 (7)	0.0043 (7)
C15	0.0699 (11)	0.1101 (15)	0.0617 (10)	−0.0595 (11)	−0.0034 (9)	−0.0006 (9)
C16	0.0441 (9)	0.1152 (16)	0.0962 (14)	−0.0423 (10)	−0.0056 (9)	−0.0179 (12)
C17	0.0447 (8)	0.0802 (11)	0.0975 (13)	−0.0169 (8)	−0.0346 (9)	−0.0135 (10)
C18	0.0436 (7)	0.0501 (7)	0.0605 (8)	−0.0152 (6)	−0.0242 (6)	−0.0034 (6)
C19	0.1082 (16)	0.0698 (11)	0.0944 (14)	−0.0083 (11)	−0.0694 (13)	0.0104 (10)
N1	0.0463 (6)	0.0503 (6)	0.0596 (7)	−0.0170 (5)	−0.0276 (5)	0.0080 (5)
O1	0.0579 (6)	0.0407 (5)	0.0587 (6)	−0.0131 (4)	−0.0190 (5)	−0.0054 (4)
O2	0.0451 (5)	0.0388 (5)	0.0712 (6)	−0.0086 (4)	−0.0302 (5)	0.0000 (4)
O3	0.0389 (5)	0.0922 (8)	0.0632 (6)	−0.0304 (5)	−0.0169 (5)	0.0098 (6)
O4	0.0582 (6)	0.0577 (6)	0.0492 (5)	−0.0273 (5)	−0.0190 (5)	0.0140 (4)
O5	0.0719 (7)	0.0639 (6)	0.0685 (7)	−0.0266 (6)	−0.0434 (6)	0.0168 (5)

C1—O1	1.3718 (17)	C11—H11A	0.9600
C1—C2	1.394 (2)	C11—H11B	0.9600
C1—C6	1.395 (2)	C11—H11C	0.9600
C2—C3	1.379 (3)	C12—O2	1.4521 (15)
C2—H2	0.9300	C12—C13	1.5102 (16)
C3—C4	1.382 (3)	C12—H12	0.9800
C3—H3	0.9300	C13—C14	1.3829 (19)
C4—C5	1.372 (3)	C13—C18	1.3959 (18)
C4—H4	0.9300	C14—C15	1.388 (2)
C5—C6	1.402 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.370 (3)
C6—C7	1.4544 (19)	C15—H15	0.9300
C7—N1	1.2775 (17)	C16—C17	1.380 (3)
C7—C8	1.5053 (16)	C16—H16	0.9300
C8—C9	1.5237 (16)	C17—C18	1.392 (2)
C8—C10	1.5327 (16)	C17—H17	0.9300
C8—C12	1.5476 (16)	C18—O5	1.3604 (18)
C9—O1	1.4352 (16)	C19—O5	1.4296 (19)
C9—H9A	0.9700	C19—H19A	0.9600
C9—H9B	0.9700	C19—H19B	0.9600
C10—O3	1.1918 (15)	C19—H19C	0.9600
C10—O4	1.3225 (15)	N1—O2	1.4229 (15)
C11—O4	1.4531 (17)
O1—C1—C2	116.64 (14)	O4—C11—H11C	109.5
O1—C1—C6	122.61 (12)	H11A—C11—H11C	109.5
C2—C1—C6	120.73 (15)	H11B—C11—H11C	109.5
C3—C2—C1	118.83 (18)	O2—C12—C13	110.92 (10)
C3—C2—H2	120.6	O2—C12—C8	102.91 (9)
C1—C2—H2	120.6	C13—C12—C8	114.29 (10)
C2—C3—C4	120.97 (17)	O2—C12—H12	109.5
C2—C3—H3	119.5	C13—C12—H12	109.5
C4—C3—H3	119.5	C8—C12—H12	109.5
C5—C4—C3	120.49 (18)	C14—C13—C18	119.30 (12)
C5—C4—H4	119.8	C14—C13—C12	122.56 (12)
C3—C4—H4	119.8	C18—C13—C12	118.14 (11)
C4—C5—C6	119.91 (19)	C13—C14—C15	120.48 (16)
C4—C5—H5	120.0	C13—C14—H14	119.8
C6—C5—H5	120.0	C15—C14—H14	119.8
C1—C6—C5	119.02 (14)	C16—C15—C14	119.62 (16)
C1—C6—C7	117.43 (12)	C16—C15—H15	120.2
C5—C6—C7	123.53 (14)	C14—C15—H15	120.2
N1—C7—C6	126.69 (12)	C15—C16—C17	121.24 (15)
N1—C7—C8	114.75 (11)	C15—C16—H16	119.4
C6—C7—C8	118.48 (11)	C17—C16—H16	119.4
C7—C8—C9	106.98 (10)	C16—C17—C18	119.23 (16)
C7—C8—C10	109.18 (9)	C16—C17—H17	120.4
C9—C8—C10	112.00 (10)	C18—C17—H17	120.4
C7—C8—C12	99.03 (9)	O5—C18—C17	124.89 (14)
C9—C8—C12	118.65 (10)	O5—C18—C13	114.98 (12)
C10—C8—C12	109.87 (9)	C17—C18—C13	120.13 (15)
O1—C9—C8	109.50 (10)	O5—C19—H19A	109.5
O1—C9—H9A	109.8	O5—C19—H19B	109.5
C8—C9—H9A	109.8	H19A—C19—H19B	109.5
O1—C9—H9B	109.8	O5—C19—H19C	109.5
C8—C9—H9B	109.8	H19A—C19—H19C	109.5
H9A—C9—H9B	108.2	H19B—C19—H19C	109.5
O3—C10—O4	124.43 (12)	C7—N1—O2	107.98 (10)
O3—C10—C8	123.42 (12)	C1—O1—C9	116.02 (10)
O4—C10—C8	112.11 (10)	N1—O2—C12	108.84 (9)
O4—C11—H11A	109.5	C10—O4—C11	115.35 (12)
O4—C11—H11B	109.5	C18—O5—C19	118.13 (14)
H11A—C11—H11B	109.5
O1—C1—C2—C3	179.39 (14)	C10—C8—C12—O2	−91.49 (11)
C6—C1—C2—C3	1.0 (2)	C7—C8—C12—C13	−97.56 (11)
C1—C2—C3—C4	1.1 (3)	C9—C8—C12—C13	17.51 (15)
C2—C3—C4—C5	−1.8 (3)	C10—C8—C12—C13	148.16 (10)
C3—C4—C5—C6	0.3 (3)	O2—C12—C13—C14	−17.90 (17)
O1—C1—C6—C5	179.24 (12)	C8—C12—C13—C14	97.88 (15)
C2—C1—C6—C5	−2.5 (2)	O2—C12—C13—C18	162.62 (11)
O1—C1—C6—C7	−2.07 (18)	C8—C12—C13—C18	−81.60 (14)
C2—C1—C6—C7	176.20 (12)	C18—C13—C14—C15	0.5 (2)
C4—C5—C6—C1	1.8 (2)	C12—C13—C14—C15	−178.98 (14)
C4—C5—C6—C7	−176.77 (15)	C13—C14—C15—C16	−0.4 (3)
C1—C6—C7—N1	168.16 (12)	C14—C15—C16—C17	0.3 (3)
C5—C6—C7—N1	−13.2 (2)	C15—C16—C17—C18	−0.1 (3)
C1—C6—C7—C8	−8.22 (17)	C16—C17—C18—O5	179.75 (16)
C5—C6—C7—C8	170.40 (12)	C16—C17—C18—C13	0.2 (2)
N1—C7—C8—C9	−138.72 (11)	C14—C13—C18—O5	−179.97 (12)
C6—C7—C8—C9	38.09 (14)	C12—C13—C18—O5	−0.47 (18)
N1—C7—C8—C10	99.88 (12)	C14—C13—C18—C17	−0.4 (2)
C6—C7—C8—C10	−83.31 (13)	C12—C13—C18—C17	179.12 (13)
N1—C7—C8—C12	−14.94 (13)	C6—C7—N1—O2	−176.52 (11)
C6—C7—C8—C12	161.87 (10)	C8—C7—N1—O2	−0.02 (14)
C7—C8—C9—O1	−59.44 (13)	C2—C1—O1—C9	159.71 (12)
C10—C8—C9—O1	60.16 (13)	C6—C1—O1—C9	−21.95 (17)
C12—C8—C9—O1	−170.16 (10)	C8—C9—O1—C1	53.68 (14)
C7—C8—C10—O3	−23.21 (17)	C7—N1—O2—C12	16.69 (13)
C9—C8—C10—O3	−141.51 (13)	C13—C12—O2—N1	97.46 (11)
C12—C8—C10—O3	84.40 (15)	C8—C12—O2—N1	−25.18 (12)
C7—C8—C10—O4	158.97 (10)	O3—C10—O4—C11	−1.54 (19)
C9—C8—C10—O4	40.67 (14)	C8—C10—O4—C11	176.26 (11)
C12—C8—C10—O4	−93.43 (12)	C17—C18—O5—C19	−1.3 (2)
C7—C8—C12—O2	22.79 (11)	C13—C18—O5—C19	178.27 (14)
C9—C8—C12—O2	137.86 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O3i	0.93	2.42	3.3084 (19)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O3i	0.93	2.42	3.3084 (19)	159

Symmetry code: (i) .