3-(3-Chloro-phen-yl)-1-methyl-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile.

In the title compound, C(18)H(15)ClN(2)O(2), the five-membered isoxazole ring adopts an envelope conformation [the deviation of the N atom is 0.3154 (15) Å] and the six-membered pyran ring adopts a half-chair conformation. The mean plane through all atoms of the isoxazole ring forms dihedral angles of 47.98 (8)° with the mean plane of the chromene ring system and 75.10 (9)° with the chloro-benzene ring.

Related literature

For the synthesis of tricyclic chromenoisoxazolidines, see: Bakthadoss & Murugan (2010 ▶). For uses of isoxazole derivatives, see: Loh et al. (2010 ▶); Winn et al. (1976 ▶). For a related structure, see: Gunasekaran et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H15ClN2O2

M = 326.77

Monoclinic,

a = 10.0141 (4) Å

b = 9.2358 (3) Å

c = 17.5945 (6) Å

β = 102.354 (2)°

V = 1589.60 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.928, T max = 0.952

20534 measured reflections

4926 independent reflections

3390 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.151

S = 1.04

4926 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007495/rk2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007495/rk2265Isup2.hkl

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

C18H15ClN2O2	F(000) = 680
Mr = 326.77	Dx = 1.365 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4926 reflections
a = 10.0141 (4) Å	θ = 1.0–25.0°
b = 9.2358 (3) Å	µ = 0.25 mm−1
c = 17.5945 (6) Å	T = 295 K
β = 102.354 (2)°	Block, colourless
V = 1589.60 (10) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4926 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 30.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.928, Tmax = 0.952	k = −13→12
20534 measured reflections	l = −25→25

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) = 0.151	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.525P] where P = (Fo2 + 2Fc2)/3
4926 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.71130 (16)	0.55309 (17)	0.60426 (9)	0.0414 (3)
C2	0.7392 (2)	0.5485 (2)	0.53022 (11)	0.0558 (5)
H2	0.6764	0.5081	0.4890	0.067*
C3	0.8604 (2)	0.6042 (3)	0.51838 (13)	0.0661 (6)
H3	0.8786	0.6031	0.4687	0.079*
C4	0.9552 (2)	0.6618 (3)	0.57932 (14)	0.0666 (6)
H4	1.0375	0.6980	0.5710	0.080*
C5	0.92754 (19)	0.6654 (2)	0.65242 (12)	0.0527 (4)
H5	0.9924	0.7029	0.6936	0.063*
C6	0.80402 (15)	0.61383 (17)	0.66604 (9)	0.0391 (3)
C7	0.77527 (14)	0.61740 (15)	0.74613 (8)	0.0347 (3)
H7	0.8576	0.5912	0.7847	0.042*
C8	0.65603 (14)	0.51912 (15)	0.75457 (8)	0.0345 (3)
C9	0.54349 (15)	0.53043 (18)	0.68020 (9)	0.0400 (3)
H9A	0.4677	0.4683	0.6851	0.048*
H9B	0.5100	0.6292	0.6743	0.048*
C10	0.60629 (16)	0.58987 (17)	0.82461 (9)	0.0392 (3)
H10	0.5095	0.6157	0.8079	0.047*
C11	0.62489 (15)	0.49933 (17)	0.89708 (9)	0.0382 (3)
C12	0.74430 (16)	0.50552 (19)	0.95373 (10)	0.0435 (4)
H12	0.8145	0.5681	0.9483	0.052*
C13	0.75772 (19)	0.4174 (2)	1.01837 (10)	0.0503 (4)
C14	0.6564 (2)	0.3247 (2)	1.02857 (12)	0.0584 (5)
H14	0.6676	0.2664	1.0726	0.070*
C15	0.5385 (2)	0.3195 (2)	0.97269 (12)	0.0621 (5)
H15	0.4687	0.2569	0.9788	0.075*
C16	0.52159 (19)	0.4062 (2)	0.90713 (11)	0.0512 (4)
H16	0.4406	0.4020	0.8697	0.061*
C17	0.8261 (2)	0.86941 (19)	0.78734 (11)	0.0531 (4)
H17A	0.7878	0.9520	0.8080	0.080*
H17B	0.8582	0.8975	0.7418	0.080*
H17C	0.9010	0.8321	0.8257	0.080*
C18	0.69897 (16)	0.36725 (17)	0.76710 (10)	0.0405 (3)
N1	0.72137 (14)	0.75768 (14)	0.76661 (7)	0.0396 (3)
N2	0.72938 (17)	0.24949 (17)	0.77403 (11)	0.0618 (4)
O1	0.59142 (12)	0.48990 (13)	0.61273 (7)	0.0470 (3)
O2	0.68515 (14)	0.71908 (12)	0.84078 (7)	0.0481 (3)
Cl1	0.90798 (6)	0.42666 (9)	1.08998 (4)	0.0900 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0467 (8)	0.0382 (8)	0.0375 (8)	0.0095 (6)	0.0049 (6)	−0.0010 (6)
C2	0.0680 (12)	0.0572 (11)	0.0404 (9)	0.0170 (9)	0.0079 (8)	−0.0024 (8)
C3	0.0852 (14)	0.0674 (13)	0.0533 (11)	0.0204 (11)	0.0318 (11)	0.0081 (10)
C4	0.0685 (12)	0.0649 (13)	0.0749 (14)	0.0032 (10)	0.0344 (11)	0.0058 (11)
C5	0.0475 (9)	0.0522 (10)	0.0595 (11)	−0.0014 (8)	0.0142 (8)	−0.0013 (8)
C6	0.0402 (7)	0.0350 (7)	0.0406 (8)	0.0046 (6)	0.0055 (6)	0.0011 (6)
C7	0.0346 (6)	0.0300 (7)	0.0355 (7)	0.0006 (5)	−0.0015 (5)	−0.0001 (5)
C8	0.0353 (7)	0.0285 (6)	0.0369 (7)	0.0029 (5)	0.0016 (5)	−0.0002 (5)
C9	0.0341 (7)	0.0415 (8)	0.0406 (8)	0.0013 (6)	−0.0007 (6)	−0.0047 (6)
C10	0.0401 (7)	0.0358 (7)	0.0402 (8)	0.0050 (6)	0.0053 (6)	−0.0013 (6)
C11	0.0402 (7)	0.0351 (7)	0.0404 (8)	0.0004 (6)	0.0111 (6)	−0.0026 (6)
C12	0.0395 (7)	0.0456 (9)	0.0454 (8)	−0.0006 (7)	0.0091 (6)	0.0074 (7)
C13	0.0550 (10)	0.0499 (10)	0.0453 (9)	0.0078 (8)	0.0091 (7)	0.0076 (7)
C14	0.0899 (14)	0.0380 (9)	0.0523 (10)	−0.0021 (9)	0.0262 (10)	0.0051 (8)
C15	0.0824 (14)	0.0455 (10)	0.0662 (12)	−0.0269 (10)	0.0331 (11)	−0.0089 (9)
C16	0.0518 (9)	0.0503 (10)	0.0517 (10)	−0.0143 (8)	0.0119 (8)	−0.0137 (8)
C17	0.0676 (11)	0.0342 (8)	0.0540 (10)	−0.0085 (8)	0.0052 (8)	−0.0031 (7)
C18	0.0404 (7)	0.0326 (7)	0.0471 (8)	0.0010 (6)	0.0061 (6)	0.0004 (6)
N1	0.0513 (7)	0.0293 (6)	0.0360 (6)	0.0008 (5)	0.0045 (5)	0.0011 (5)
N2	0.0636 (10)	0.0364 (8)	0.0845 (12)	0.0068 (7)	0.0135 (9)	0.0031 (8)
O1	0.0452 (6)	0.0517 (7)	0.0392 (6)	−0.0014 (5)	−0.0016 (5)	−0.0116 (5)
O2	0.0751 (8)	0.0314 (6)	0.0395 (6)	−0.0028 (5)	0.0158 (5)	−0.0031 (4)
Cl1	0.0704 (4)	0.1252 (6)	0.0635 (4)	0.0115 (4)	−0.0098 (3)	0.0284 (3)

C1—O1	1.371 (2)	C10—O2	1.4257 (19)
C1—C6	1.388 (2)	C10—C11	1.503 (2)
C1—C2	1.390 (2)	C10—H10	0.9800
C2—C3	1.375 (3)	C11—C12	1.384 (2)
C2—H2	0.9300	C11—C16	1.385 (2)
C3—C4	1.378 (3)	C12—C13	1.381 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.373 (3)	C13—C14	1.369 (3)
C4—H4	0.9300	C13—Cl1	1.7459 (19)
C5—C6	1.393 (2)	C14—C15	1.366 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.498 (2)	C15—C16	1.385 (3)
C7—N1	1.4775 (19)	C15—H15	0.9300
C7—C8	1.532 (2)	C16—H16	0.9300
C7—H7	0.9800	C17—N1	1.461 (2)
C8—C18	1.470 (2)	C17—H17A	0.9600
C8—C9	1.537 (2)	C17—H17B	0.9600
C8—C10	1.567 (2)	C17—H17C	0.9600
C9—O1	1.423 (2)	C18—N2	1.129 (2)
C9—H9A	0.9700	N1—O2	1.4711 (17)
C9—H9B	0.9700
O1—C1—C6	122.77 (14)	O2—C10—C11	109.49 (12)
O1—C1—C2	116.42 (15)	O2—C10—C8	104.48 (12)
C6—C1—C2	120.75 (17)	C11—C10—C8	115.63 (12)
C3—C2—C1	119.44 (19)	O2—C10—H10	109.0
C3—C2—H2	120.3	C11—C10—H10	109.0
C1—C2—H2	120.3	C8—C10—H10	109.0
C2—C3—C4	120.68 (19)	C12—C11—C16	119.17 (16)
C2—C3—H3	119.7	C12—C11—C10	121.27 (14)
C4—C3—H3	119.7	C16—C11—C10	119.56 (15)
C5—C4—C3	119.7 (2)	C13—C12—C11	119.03 (16)
C5—C4—H4	120.2	C13—C12—H12	120.5
C3—C4—H4	120.2	C11—C12—H12	120.5
C4—C5—C6	121.15 (19)	C14—C13—C12	122.17 (17)
C4—C5—H5	119.4	C14—C13—Cl1	118.99 (15)
C6—C5—H5	119.4	C12—C13—Cl1	118.84 (14)
C1—C6—C5	118.25 (16)	C15—C14—C13	118.59 (17)
C1—C6—C7	120.97 (14)	C15—C14—H14	120.7
C5—C6—C7	120.71 (15)	C13—C14—H14	120.7
N1—C7—C6	113.74 (12)	C14—C15—C16	120.76 (17)
N1—C7—C8	99.38 (11)	C14—C15—H15	119.6
C6—C7—C8	112.88 (12)	C16—C15—H15	119.6
N1—C7—H7	110.1	C15—C16—C11	120.27 (17)
C6—C7—H7	110.1	C15—C16—H16	119.9
C8—C7—H7	110.1	C11—C16—H16	119.9
C18—C8—C7	111.76 (12)	N1—C17—H17A	109.5
C18—C8—C9	109.29 (12)	N1—C17—H17B	109.5
C7—C8—C9	108.78 (12)	H17A—C17—H17B	109.5
C18—C8—C10	114.32 (13)	N1—C17—H17C	109.5
C7—C8—C10	102.39 (11)	H17A—C17—H17C	109.5
C9—C8—C10	110.04 (12)	H17B—C17—H17C	109.5
O1—C9—C8	112.07 (12)	N2—C18—C8	177.46 (19)
O1—C9—H9A	109.2	C17—N1—O2	104.46 (12)
C8—C9—H9A	109.2	C17—N1—C7	113.60 (13)
O1—C9—H9B	109.2	O2—N1—C7	100.14 (10)
C8—C9—H9B	109.2	C1—O1—C9	115.99 (12)
H9A—C9—H9B	107.9	C10—O2—N1	104.90 (11)
O1—C1—C2—C3	−177.20 (17)	C7—C8—C10—C11	−114.23 (14)
C6—C1—C2—C3	0.3 (3)	C9—C8—C10—C11	130.25 (14)
C1—C2—C3—C4	1.3 (3)	O2—C10—C11—C12	−28.6 (2)
C2—C3—C4—C5	−0.9 (3)	C8—C10—C11—C12	89.10 (18)
C3—C4—C5—C6	−1.0 (3)	O2—C10—C11—C16	152.35 (14)
O1—C1—C6—C5	175.18 (15)	C8—C10—C11—C16	−89.99 (18)
C2—C1—C6—C5	−2.2 (2)	C16—C11—C12—C13	0.7 (2)
O1—C1—C6—C7	−1.9 (2)	C10—C11—C12—C13	−178.38 (15)
C2—C1—C6—C7	−179.23 (15)	C11—C12—C13—C14	−0.4 (3)
C4—C5—C6—C1	2.5 (3)	C11—C12—C13—Cl1	−179.51 (13)
C4—C5—C6—C7	179.59 (17)	C12—C13—C14—C15	0.1 (3)
C1—C6—C7—N1	−98.81 (17)	Cl1—C13—C14—C15	179.19 (15)
C5—C6—C7—N1	84.21 (18)	C13—C14—C15—C16	−0.1 (3)
C1—C6—C7—C8	13.4 (2)	C14—C15—C16—C11	0.4 (3)
C5—C6—C7—C8	−163.53 (14)	C12—C11—C16—C15	−0.7 (3)
N1—C7—C8—C18	−158.11 (12)	C10—C11—C16—C15	178.42 (16)
C6—C7—C8—C18	81.06 (15)	C6—C7—N1—C17	−77.41 (16)
N1—C7—C8—C9	81.13 (13)	C8—C7—N1—C17	162.38 (12)
C6—C7—C8—C9	−39.70 (16)	C6—C7—N1—O2	171.80 (12)
N1—C7—C8—C10	−35.30 (13)	C8—C7—N1—O2	51.59 (12)
C6—C7—C8—C10	−156.14 (12)	C6—C1—O1—C9	20.4 (2)
C18—C8—C9—O1	−63.51 (17)	C2—C1—O1—C9	−162.18 (15)
C7—C8—C9—O1	58.76 (16)	C8—C9—O1—C1	−49.34 (18)
C10—C8—C9—O1	170.19 (12)	C11—C10—O2—N1	150.44 (12)
C18—C8—C10—O2	127.25 (13)	C8—C10—O2—N1	26.01 (14)
C7—C8—C10—O2	6.19 (14)	C17—N1—O2—C10	−167.72 (13)
C9—C8—C10—O2	−109.34 (13)	C7—N1—O2—C10	−49.94 (13)
C18—C8—C10—C11	6.83 (18)