5-(4-Chloro-phen-yl)-6-isopropyl-5,6-dihydro-4H-pyrrolo-[3,4-c]isoxazole.

The title compound, C(14)H(15)ClN(2)O, contains an eight-membered 5,5-fused bicycle with two substituents. The dihedral angle between the nearly planar eight-membered ring [maximum deviation = 0.033 (2) Å] and the benzene ring is 25.0 (1)°. In the crystal structure, mol-ecules are stacked in columns along the b axis and C-H⋯π inter-actions are observed between the columns.

Related literature

For the synthesis of the title compound, see: Kim & Lee (1994 ▶). For the biological activity of isoxazoles, see: Boyd (1991 ▶); Kim et al. (1994 ▶, 1997 ▶, 1999 ▶); Lang & Lin (1984 ▶); Sutharchanadevi & Murugan (1996 ▶).

Experimental

Crystal data

C14H15ClN2O

M = 262.73

Monoclinic,

a = 15.0037 (9) Å

b = 6.2364 (4) Å

c = 15.5801 (9) Å

β = 117.238 (1)°

V = 1296.16 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 200 K

0.35 × 0.28 × 0.12 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.861, T max = 0.966

9224 measured reflections

3211 independent reflections

1907 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.117

S = 1.07

3211 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034872/is2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034872/is2594Isup2.hkl

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

C14H15ClN2O	F(000) = 552
Mr = 262.73	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2659 reflections
a = 15.0037 (9) Å	θ = 2.6–27.1°
b = 6.2364 (4) Å	µ = 0.28 mm−1
c = 15.5801 (9) Å	T = 200 K
β = 117.238 (1)°	Stick, pale yellow
V = 1296.16 (14) Å3	0.35 × 0.28 × 0.12 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube	1907 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −19→20
Tmin = 0.861, Tmax = 0.966	k = −8→8
9224 measured reflections	l = −18→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0311P)2 + 0.6269P] where P = (Fo2 + 2Fc2)/3
3211 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.44 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
Cl1	0.53029 (5)	0.72970 (11)	0.07428 (5)	0.0460 (2)
O1	0.17957 (13)	1.1528 (3)	0.45555 (12)	0.0468 (5)
N1	0.25711 (13)	0.8986 (3)	0.24578 (13)	0.0292 (4)
N2	0.17208 (15)	1.2612 (3)	0.37156 (14)	0.0400 (5)
C1	0.31613 (16)	0.8552 (4)	0.20076 (15)	0.0284 (5)
C2	0.32447 (17)	1.0003 (4)	0.13595 (16)	0.0317 (5)
H2	0.2857	1.1280	0.1193	0.038*
C3	0.38835 (17)	0.9599 (4)	0.09593 (16)	0.0341 (5)
H3	0.3940	1.0608	0.0530	0.041*
C4	0.44355 (17)	0.7739 (4)	0.11838 (16)	0.0327 (5)
C5	0.43342 (16)	0.6228 (4)	0.17806 (16)	0.0333 (5)
H5	0.4696	0.4918	0.1911	0.040*
C6	0.37017 (16)	0.6630 (4)	0.21896 (16)	0.0316 (5)
H6	0.3634	0.5586	0.2600	0.038*
C7	0.27190 (18)	0.7731 (4)	0.33222 (17)	0.0341 (5)
H7A	0.3437	0.7411	0.3738	0.041*
H7B	0.2335	0.6372	0.3140	0.041*
C8	0.23192 (17)	0.9227 (4)	0.38036 (16)	0.0322 (5)
C9	0.21539 (18)	0.9522 (4)	0.45747 (17)	0.0412 (6)
H9	0.2271	0.8481	0.5060	0.049*
C10	0.20329 (16)	1.1175 (4)	0.33080 (16)	0.0298 (5)
C11	0.21313 (16)	1.1144 (4)	0.23924 (15)	0.0279 (5)
H11	0.2625	1.2261	0.2426	0.034*
C12	0.11400 (17)	1.1478 (4)	0.14745 (16)	0.0325 (5)
H12	0.1255	1.1103	0.0909	0.039*
C13	0.0833 (2)	1.3827 (4)	0.13769 (19)	0.0464 (7)
H13A	0.0713	1.4239	0.1922	0.070*
H13B	0.0218	1.4036	0.0772	0.070*
H13C	0.1369	1.4716	0.1373	0.070*
C14	0.03096 (18)	1.0035 (4)	0.14450 (19)	0.0488 (7)
H14A	0.0132	1.0470	0.1951	0.073*
H14B	0.0542	0.8544	0.1551	0.073*
H14C	−0.0280	1.0161	0.0813	0.073*

	U11	U22	U33	U12	U13	U23
Cl1	0.0449 (4)	0.0560 (4)	0.0462 (4)	0.0075 (3)	0.0287 (3)	−0.0022 (3)
O1	0.0517 (11)	0.0585 (12)	0.0343 (10)	0.0084 (9)	0.0233 (9)	−0.0015 (9)
N1	0.0326 (10)	0.0275 (10)	0.0298 (10)	0.0036 (8)	0.0164 (8)	0.0050 (8)
N2	0.0474 (12)	0.0423 (12)	0.0348 (11)	0.0057 (10)	0.0226 (10)	0.0010 (10)
C1	0.0285 (12)	0.0294 (12)	0.0256 (12)	−0.0007 (10)	0.0109 (9)	−0.0007 (9)
C2	0.0340 (13)	0.0306 (12)	0.0314 (13)	0.0048 (10)	0.0158 (10)	0.0041 (10)
C3	0.0370 (13)	0.0362 (14)	0.0310 (13)	−0.0029 (11)	0.0172 (11)	0.0018 (10)
C4	0.0322 (12)	0.0364 (13)	0.0315 (13)	0.0016 (11)	0.0163 (10)	−0.0042 (10)
C5	0.0312 (12)	0.0306 (13)	0.0340 (13)	0.0033 (10)	0.0115 (10)	−0.0008 (10)
C6	0.0300 (12)	0.0314 (12)	0.0308 (12)	0.0003 (10)	0.0117 (10)	0.0027 (10)
C7	0.0414 (13)	0.0312 (13)	0.0331 (13)	0.0030 (11)	0.0199 (11)	0.0064 (10)
C8	0.0317 (12)	0.0369 (13)	0.0291 (12)	−0.0003 (11)	0.0148 (10)	0.0034 (10)
C9	0.0400 (14)	0.0509 (16)	0.0330 (14)	0.0066 (12)	0.0171 (11)	0.0067 (12)
C10	0.0264 (11)	0.0332 (13)	0.0294 (12)	−0.0006 (10)	0.0124 (10)	−0.0002 (10)
C11	0.0275 (11)	0.0290 (12)	0.0286 (12)	−0.0002 (10)	0.0139 (9)	0.0017 (9)
C12	0.0322 (13)	0.0359 (13)	0.0283 (12)	0.0036 (10)	0.0128 (10)	0.0030 (10)
C13	0.0456 (15)	0.0455 (16)	0.0449 (16)	0.0111 (13)	0.0180 (13)	0.0129 (13)
C14	0.0350 (14)	0.0522 (17)	0.0492 (16)	−0.0046 (13)	0.0106 (12)	0.0032 (13)

Cl1—C4	1.749 (2)	C7—H7A	0.9900
O1—C9	1.356 (3)	C7—H7B	0.9900
O1—N2	1.431 (2)	C8—C9	1.346 (3)
N1—C1	1.385 (3)	C8—C10	1.398 (3)
N1—C11	1.482 (3)	C9—H9	0.9500
N1—C7	1.484 (3)	C10—C11	1.500 (3)
N2—C10	1.303 (3)	C11—C12	1.534 (3)
C1—C6	1.401 (3)	C11—H11	1.0000
C1—C2	1.403 (3)	C12—C14	1.521 (3)
C2—C3	1.385 (3)	C12—C13	1.522 (3)
C2—H2	0.9500	C12—H12	1.0000
C3—C4	1.374 (3)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.380 (3)	C13—H13C	0.9800
C5—C6	1.387 (3)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C6—H6	0.9500	C14—H14C	0.9800
C7—C8	1.485 (3)
C9—O1—N2	108.68 (17)	C10—C8—C7	111.13 (19)
C1—N1—C11	120.72 (17)	C8—C9—O1	109.8 (2)
C1—N1—C7	119.44 (18)	C8—C9—H9	125.1
C11—N1—C7	114.75 (16)	O1—C9—H9	125.1
C10—N2—O1	103.03 (18)	N2—C10—C8	114.6 (2)
N1—C1—C6	120.6 (2)	N2—C10—C11	133.3 (2)
N1—C1—C2	121.8 (2)	C8—C10—C11	112.02 (19)
C6—C1—C2	117.59 (19)	N1—C11—C10	100.43 (17)
C3—C2—C1	121.0 (2)	N1—C11—C12	113.51 (18)
C3—C2—H2	119.5	C10—C11—C12	114.16 (17)
C1—C2—H2	119.5	N1—C11—H11	109.5
C4—C3—C2	120.0 (2)	C10—C11—H11	109.5
C4—C3—H3	120.0	C12—C11—H11	109.5
C2—C3—H3	120.0	C14—C12—C13	111.1 (2)
C3—C4—C5	120.6 (2)	C14—C12—C11	112.28 (19)
C3—C4—Cl1	120.21 (18)	C13—C12—C11	110.13 (19)
C5—C4—Cl1	119.21 (18)	C14—C12—H12	107.7
C4—C5—C6	119.7 (2)	C13—C12—H12	107.7
C4—C5—H5	120.1	C11—C12—H12	107.7
C6—C5—H5	120.1	C12—C13—H13A	109.5
C5—C6—C1	121.0 (2)	C12—C13—H13B	109.5
C5—C6—H6	119.5	H13A—C13—H13B	109.5
C1—C6—H6	119.5	C12—C13—H13C	109.5
N1—C7—C8	101.51 (17)	H13A—C13—H13C	109.5
N1—C7—H7A	111.5	H13B—C13—H13C	109.5
C8—C7—H7A	111.5	C12—C14—H14A	109.5
N1—C7—H7B	111.5	C12—C14—H14B	109.5
C8—C7—H7B	111.5	H14A—C14—H14B	109.5
H7A—C7—H7B	109.3	C12—C14—H14C	109.5
C9—C8—C10	103.8 (2)	H14A—C14—H14C	109.5
C9—C8—C7	145.0 (2)	H14B—C14—H14C	109.5
C9—O1—N2—C10	0.3 (2)	C7—C8—C9—O1	175.2 (3)
C11—N1—C1—C6	170.09 (19)	N2—O1—C9—C8	0.1 (3)
C7—N1—C1—C6	16.6 (3)	O1—N2—C10—C8	−0.5 (3)
C11—N1—C1—C2	−9.7 (3)	O1—N2—C10—C11	177.8 (2)
C7—N1—C1—C2	−163.2 (2)	C9—C8—C10—N2	0.6 (3)
N1—C1—C2—C3	176.2 (2)	C7—C8—C10—N2	−176.7 (2)
C6—C1—C2—C3	−3.7 (3)	C9—C8—C10—C11	−178.10 (19)
C1—C2—C3—C4	1.0 (3)	C7—C8—C10—C11	4.6 (3)
C2—C3—C4—C5	2.2 (3)	C1—N1—C11—C10	−153.36 (19)
C2—C3—C4—Cl1	−175.91 (18)	C7—N1—C11—C10	1.3 (2)
C3—C4—C5—C6	−2.7 (3)	C1—N1—C11—C12	84.4 (2)
Cl1—C4—C5—C6	175.43 (17)	C7—N1—C11—C12	−121.0 (2)
C4—C5—C6—C1	0.0 (3)	N2—C10—C11—N1	178.2 (2)
N1—C1—C6—C5	−176.7 (2)	C8—C10—C11—N1	−3.5 (2)
C2—C1—C6—C5	3.2 (3)	N2—C10—C11—C12	−60.0 (3)
C1—N1—C7—C8	156.14 (19)	C8—C10—C11—C12	118.3 (2)
C11—N1—C7—C8	1.2 (2)	N1—C11—C12—C14	65.4 (2)
N1—C7—C8—C9	−178.9 (3)	C10—C11—C12—C14	−48.9 (3)
N1—C7—C8—C10	−3.4 (2)	N1—C11—C12—C13	−170.28 (18)
C10—C8—C9—O1	−0.4 (3)	C10—C11—C12—C13	75.4 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1i	0.95	2.65	3.405 (3)	136
C9—H9···Cg1ii	0.95	2.62	3.392 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.95	2.65	3.405 (3)	136
C9—H9⋯Cg1ii	0.95	2.62	3.392 (3)	138

Symmetry codes: (i) ; (ii) .