rac-3-(4-Chloro-phen-yl)-3a,4-di-hydro-3H-chromeno[4,3-c]isoxazole-3a-carbo-nitrile.

The title compound, C17H11ClN2O2, which contains two stereogenic C atoms, crystallizes in a centrosymmetric space group as a racemate. The pyran ring and the isoxazole ring adopt sofa and twisted conformations, respectively. The dihedral angle between the benzene ring and the mean plane through the near coplanar atoms of the pyran ring is 4.17 (5)°. The mol-ecular conformation features a weak C-H⋯O contact. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules, forming chains along the a-axis direction.

Related literature

For the biological activity of isoxazole derivatives, see: Mullen et al. (1988 ▶); Eddington et al. (2002 ▶); Kashiwada et al. (2001 ▶); Caine (1993 ▶). For a related structure, see: Paramasivam et al. (2012 ▶). For conformational analysis and pukering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H11ClN2O2

M = 310.73

Monoclinic,

a = 6.7891 (2) Å

b = 13.9921 (3) Å

c = 15.1788 (3) Å

β = 101.175 (1)°

V = 1414.55 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.28 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 = 0.921, T max = 0.946

13620 measured reflections

3541 independent reflections

2865 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.132

S = 1.00

3541 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.37 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/S1600536813009653/kp2448sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009653/kp2448Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009653/kp2448Isup3.cml

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

C17H11ClN2O2	F(000) = 640
Mr = 310.73	Monoclinic
Monoclinic, P21/c	Dx = 1.459 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.7891 (2) Å	Cell parameters from 3541 reflections
b = 13.9921 (3) Å	θ = 2.0–28.4°
c = 15.1788 (3) Å	µ = 0.28 mm−1
β = 101.175 (1)°	T = 298 K
V = 1414.55 (6) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker SMART APEXII area-detector diffractometer	3541 independent reflections
Radiation source: fine-focus sealed tube	2865 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→8
Tmin = 0.921, Tmax = 0.946	k = −18→11
13620 measured reflections	l = −20→20

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) = 0.132	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0796P)2 + 0.2931P] where P = (Fo2 + 2Fc2)/3
3541 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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	0.7698 (2)	0.37043 (10)	0.51654 (9)	0.0382 (3)
C2	0.7964 (3)	0.34701 (12)	0.60681 (10)	0.0497 (4)
H2	0.6880	0.3473	0.6360	0.060*
C3	0.9865 (3)	0.32316 (13)	0.65285 (10)	0.0565 (4)
H3	1.0052	0.3066	0.7132	0.068*
C4	1.1478 (3)	0.32362 (12)	0.61050 (11)	0.0551 (4)
H4	1.2747	0.3077	0.6424	0.066*
C5	1.1226 (2)	0.34766 (11)	0.52083 (11)	0.0457 (3)
H5	1.2326	0.3483	0.4926	0.055*
C6	0.9322 (2)	0.37097 (9)	0.47255 (9)	0.0360 (3)
C7	0.89137 (18)	0.39271 (10)	0.37728 (9)	0.0350 (3)
C8	0.67441 (18)	0.39375 (10)	0.32830 (8)	0.0330 (3)
C9	0.5486 (2)	0.43971 (11)	0.38997 (9)	0.0402 (3)
H9A	0.5883	0.5059	0.4008	0.048*
H9B	0.4079	0.4384	0.3613	0.048*
C10	0.6106 (2)	0.29492 (11)	0.30501 (8)	0.0383 (3)
C11	0.7019 (2)	0.45257 (10)	0.24579 (9)	0.0382 (3)
H11	0.6890	0.5206	0.2592	0.046*
C12	0.5619 (2)	0.42986 (10)	0.15911 (8)	0.0369 (3)
C13	0.6257 (3)	0.38630 (11)	0.08816 (10)	0.0459 (3)
H13	0.7603	0.3701	0.0933	0.055*
C14	0.4913 (3)	0.36634 (11)	0.00910 (11)	0.0533 (4)
H14	0.5353	0.3378	−0.0390	0.064*
C15	0.2925 (3)	0.38934 (12)	0.00299 (10)	0.0509 (4)
C16	0.2244 (3)	0.43228 (14)	0.07288 (11)	0.0553 (4)
H16	0.0891	0.4470	0.0679	0.066*
C17	0.3603 (2)	0.45313 (13)	0.15060 (10)	0.0490 (4)
H17	0.3162	0.4832	0.1979	0.059*
N1	1.01637 (18)	0.41374 (11)	0.32770 (8)	0.0479 (3)
N2	0.5647 (2)	0.21792 (11)	0.28725 (9)	0.0577 (4)
O1	0.90826 (15)	0.43321 (10)	0.23971 (7)	0.0530 (3)
O2	0.57595 (15)	0.38915 (8)	0.47380 (7)	0.0463 (3)
Cl1	0.12337 (10)	0.36499 (4)	−0.09593 (3)	0.0808 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0393 (7)	0.0430 (7)	0.0311 (6)	−0.0037 (5)	0.0038 (5)	−0.0036 (5)
C2	0.0611 (10)	0.0557 (9)	0.0320 (7)	−0.0063 (7)	0.0085 (6)	−0.0012 (6)
C3	0.0750 (12)	0.0552 (10)	0.0329 (7)	−0.0091 (8)	−0.0050 (7)	0.0026 (6)
C4	0.0534 (9)	0.0536 (9)	0.0478 (8)	−0.0034 (7)	−0.0161 (7)	0.0026 (7)
C5	0.0364 (7)	0.0490 (8)	0.0469 (8)	−0.0039 (6)	−0.0034 (6)	−0.0004 (6)
C6	0.0344 (6)	0.0382 (7)	0.0330 (6)	−0.0043 (5)	0.0005 (5)	−0.0019 (5)
C7	0.0275 (6)	0.0414 (7)	0.0353 (6)	−0.0025 (5)	0.0041 (5)	−0.0016 (5)
C8	0.0282 (6)	0.0424 (7)	0.0279 (5)	−0.0019 (5)	0.0040 (4)	−0.0002 (5)
C9	0.0333 (6)	0.0547 (8)	0.0323 (6)	0.0039 (6)	0.0059 (5)	−0.0008 (6)
C10	0.0384 (7)	0.0481 (8)	0.0273 (5)	−0.0052 (6)	0.0040 (5)	0.0014 (5)
C11	0.0353 (7)	0.0451 (7)	0.0343 (6)	−0.0034 (5)	0.0073 (5)	0.0030 (5)
C12	0.0418 (7)	0.0389 (7)	0.0298 (6)	−0.0008 (5)	0.0064 (5)	0.0056 (5)
C13	0.0528 (9)	0.0471 (8)	0.0391 (7)	0.0062 (6)	0.0120 (6)	0.0014 (6)
C14	0.0770 (12)	0.0459 (9)	0.0366 (7)	0.0024 (8)	0.0102 (7)	−0.0040 (6)
C15	0.0699 (11)	0.0439 (8)	0.0331 (7)	−0.0089 (7)	−0.0049 (7)	0.0075 (6)
C16	0.0475 (9)	0.0734 (11)	0.0413 (8)	0.0023 (8)	−0.0009 (6)	0.0090 (7)
C17	0.0445 (8)	0.0679 (10)	0.0334 (7)	0.0071 (7)	0.0049 (6)	0.0014 (6)
N1	0.0330 (6)	0.0693 (9)	0.0407 (6)	−0.0043 (6)	0.0055 (5)	0.0062 (6)
N2	0.0748 (10)	0.0515 (8)	0.0436 (7)	−0.0157 (7)	0.0038 (7)	−0.0009 (6)
O1	0.0353 (5)	0.0865 (9)	0.0387 (5)	−0.0052 (5)	0.0106 (4)	0.0121 (5)
O2	0.0362 (5)	0.0721 (7)	0.0316 (5)	0.0020 (5)	0.0095 (4)	0.0032 (4)
Cl1	0.1073 (5)	0.0743 (4)	0.0450 (3)	−0.0153 (3)	−0.0245 (3)	0.0034 (2)

C1—O2	1.3750 (17)	C9—H9A	0.9700
C1—C2	1.3863 (19)	C9—H9B	0.9700
C1—C6	1.396 (2)	C10—N2	1.139 (2)
C2—C3	1.384 (3)	C11—O1	1.4477 (17)
C2—H2	0.9300	C11—C12	1.5001 (18)
C3—C4	1.373 (3)	C11—H11	0.9800
C3—H3	0.9300	C12—C13	1.378 (2)
C4—C5	1.380 (2)	C12—C17	1.388 (2)
C4—H4	0.9300	C13—C14	1.388 (2)
C5—C6	1.3953 (19)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.373 (3)
C6—C7	1.4509 (18)	C14—H14	0.9300
C7—N1	1.2731 (18)	C15—C16	1.375 (3)
C7—C8	1.5160 (17)	C15—Cl1	1.7380 (16)
C8—C10	1.4716 (19)	C16—C17	1.381 (2)
C8—C9	1.5264 (18)	C16—H16	0.9300
C8—C11	1.5398 (18)	C17—H17	0.9300
C9—O2	1.4361 (17)	N1—O1	1.4202 (16)
O2—C1—C2	116.15 (13)	C8—C9—H9B	109.6
O2—C1—C6	123.10 (12)	H9A—C9—H9B	108.1
C2—C1—C6	120.71 (14)	N2—C10—C8	178.78 (16)
C3—C2—C1	119.08 (15)	O1—C11—C12	111.15 (11)
C3—C2—H2	120.5	O1—C11—C8	102.89 (10)
C1—C2—H2	120.5	C12—C11—C8	116.37 (11)
C4—C3—C2	120.85 (15)	O1—C11—H11	108.7
C4—C3—H3	119.6	C12—C11—H11	108.7
C2—C3—H3	119.6	C8—C11—H11	108.7
C3—C4—C5	120.35 (15)	C13—C12—C17	118.99 (13)
C3—C4—H4	119.8	C13—C12—C11	122.50 (13)
C5—C4—H4	119.8	C17—C12—C11	118.51 (12)
C4—C5—C6	119.99 (15)	C12—C13—C14	120.73 (15)
C4—C5—H5	120.0	C12—C13—H13	119.6
C6—C5—H5	120.0	C14—C13—H13	119.6
C1—C6—C5	119.01 (13)	C15—C14—C13	118.96 (15)
C1—C6—C7	117.50 (12)	C15—C14—H14	120.5
C5—C6—C7	123.45 (13)	C13—C14—H14	120.5
N1—C7—C6	128.10 (12)	C14—C15—C16	121.56 (15)
N1—C7—C8	113.80 (12)	C14—C15—Cl1	119.25 (13)
C6—C7—C8	118.09 (11)	C16—C15—Cl1	119.19 (15)
C10—C8—C7	108.77 (11)	C15—C16—C17	118.86 (16)
C10—C8—C9	111.69 (11)	C15—C16—H16	120.6
C7—C8—C9	108.02 (10)	C17—C16—H16	120.6
C10—C8—C11	112.54 (11)	C16—C17—C12	120.89 (15)
C7—C8—C11	98.32 (10)	C16—C17—H17	119.6
C9—C8—C11	116.36 (12)	C12—C17—H17	119.6
O2—C9—C8	110.13 (11)	C7—N1—O1	108.55 (11)
O2—C9—H9A	109.6	N1—O1—C11	107.83 (10)
C8—C9—H9A	109.6	C1—O2—C9	117.36 (11)
O2—C9—H9B	109.6
O2—C1—C2—C3	177.14 (15)	C9—C8—C11—O1	141.41 (12)
C6—C1—C2—C3	−0.6 (2)	C10—C8—C11—C12	33.88 (17)
C1—C2—C3—C4	0.8 (3)	C7—C8—C11—C12	148.26 (12)
C2—C3—C4—C5	−0.2 (3)	C9—C8—C11—C12	−96.82 (15)
C3—C4—C5—C6	−0.5 (3)	O1—C11—C12—C13	6.67 (19)
O2—C1—C6—C5	−177.67 (13)	C8—C11—C12—C13	−110.64 (16)
C2—C1—C6—C5	−0.1 (2)	O1—C11—C12—C17	−173.80 (13)
O2—C1—C6—C7	0.2 (2)	C8—C11—C12—C17	68.89 (18)
C2—C1—C6—C7	177.75 (13)	C17—C12—C13—C14	0.4 (2)
C4—C5—C6—C1	0.6 (2)	C11—C12—C13—C14	179.89 (14)
C4—C5—C6—C7	−177.06 (14)	C12—C13—C14—C15	−1.0 (2)
C1—C6—C7—N1	166.36 (15)	C13—C14—C15—C16	0.6 (3)
C5—C6—C7—N1	−15.9 (2)	C13—C14—C15—Cl1	179.77 (12)
C1—C6—C7—C8	−11.99 (18)	C14—C15—C16—C17	0.5 (3)
C5—C6—C7—C8	165.74 (13)	Cl1—C15—C16—C17	−178.73 (13)
N1—C7—C8—C10	99.59 (14)	C15—C16—C17—C12	−1.1 (3)
C6—C7—C8—C10	−81.84 (14)	C13—C12—C17—C16	0.7 (2)
N1—C7—C8—C9	−139.02 (14)	C11—C12—C17—C16	−178.84 (15)
C6—C7—C8—C9	39.55 (16)	C6—C7—N1—O1	−177.66 (13)
N1—C7—C8—C11	−17.73 (16)	C8—C7—N1—O1	0.74 (18)
C6—C7—C8—C11	160.85 (12)	C7—N1—O1—C11	18.43 (17)
C10—C8—C9—O2	63.03 (14)	C12—C11—O1—N1	−153.97 (12)
C7—C8—C9—O2	−56.54 (15)	C8—C11—O1—N1	−28.73 (14)
C11—C8—C9—O2	−165.87 (11)	C2—C1—O2—C9	162.27 (13)
C10—C8—C11—O1	−87.89 (13)	C6—C1—O2—C9	−20.0 (2)
C7—C8—C11—O1	26.48 (13)	C8—C9—O2—C1	48.97 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.42	2.7733 (19)	102
C5—H5···O2i	0.93	2.47	3.3422 (19)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.42	2.7733 (19)	102
C5—H5⋯O2i	0.93	2.47	3.3422 (19)	156

Symmetry code: (i) .