N-(4-Chloro-phen-yl)-7-oxabicyclo-[2.2.1]hept-5-ene-2,3-dicarboximide.

In the title racemic compound, C(14)H(10)ClNO(3), which contains four stereogenic centres, the cyclo-hexane ring tends towards a boat conformation, while the tetra-hydro-furan and dihydro-furan rings adopt envelope conformations. The dihedral angle between the mean planes of the pyrrolidine-2,5-dione unit and the 4-chloro-phenyl ring is 49.0 (2)°.

Related literature

For the biological activity of 7-oxa-bicyclo­[2,2,1]hept-5-ene-2,3-dicarb­oxy­lic anhydride, see: Deng & Hu (2007 ▶). For related structures, see: Goh et al. (2008 ▶); Hart et al. (2004 ▶).

Experimental

Crystal data

C14H10ClNO3

M = 275.68

Monoclinic,

a = 10.4946 (11) Å

b = 8.2890 (8) Å

c = 14.0871 (13) Å

β = 91.538 (1)°

V = 1225.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.40 × 0.33 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.885, T max = 0.937

5907 measured reflections

2156 independent reflections

1466 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.07

2156 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047537/is2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047537/is2633Isup2.hkl

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

C14H10ClNO3	F(000) = 568
Mr = 275.68	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1615 reflections
a = 10.4946 (11) Å	θ = 2.9–24.8°
b = 8.2890 (8) Å	µ = 0.31 mm−1
c = 14.0871 (13) Å	T = 298 K
β = 91.538 (1)°	Block, light yellow
V = 1225.0 (2) Å3	0.40 × 0.33 × 0.21 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2156 independent reflections
Radiation source: fine-focus sealed tube	1466 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.885, Tmax = 0.937	k = −9→9
5907 measured reflections	l = −13→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.4264P] where P = (Fo2 + 2Fc2)/3
2156 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.33 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	1.06821 (7)	0.52842 (11)	0.16059 (6)	0.0601 (3)
N1	0.58629 (19)	0.2856 (3)	0.31440 (13)	0.0349 (5)
O1	0.66611 (17)	0.1666 (3)	0.45091 (12)	0.0482 (5)
O2	0.45183 (18)	0.3870 (3)	0.19755 (13)	0.0556 (6)
O3	0.37280 (17)	0.4471 (2)	0.44140 (13)	0.0444 (5)
C1	0.5766 (3)	0.2056 (3)	0.40149 (18)	0.0369 (6)
C2	0.4383 (2)	0.1821 (3)	0.42057 (17)	0.0361 (6)
H2	0.4176	0.0697	0.4354	0.043*
C3	0.3661 (2)	0.2439 (3)	0.33183 (17)	0.0353 (6)
H3	0.3157	0.1598	0.2994	0.042*
C4	0.4678 (2)	0.3141 (3)	0.27085 (18)	0.0369 (6)
C5	0.7041 (2)	0.3409 (3)	0.27702 (17)	0.0325 (6)
C6	0.7316 (2)	0.3134 (3)	0.18301 (17)	0.0377 (7)
H6	0.6748	0.2558	0.1442	0.045*
C7	0.8436 (2)	0.3715 (3)	0.14685 (18)	0.0397 (7)
H7	0.8623	0.3545	0.0835	0.048*
C8	0.9268 (2)	0.4544 (3)	0.2053 (2)	0.0407 (7)
C9	0.9002 (2)	0.4827 (3)	0.2991 (2)	0.0432 (7)
H9	0.9575	0.5398	0.3377	0.052*
C10	0.7882 (2)	0.4258 (3)	0.33505 (18)	0.0381 (7)
H10	0.7692	0.4445	0.3982	0.046*
C11	0.3888 (3)	0.3030 (4)	0.49633 (18)	0.0427 (7)
H11	0.4427	0.3138	0.5539	0.051*
C12	0.2531 (3)	0.2520 (4)	0.5124 (2)	0.0519 (8)
H12	0.2220	0.1981	0.5648	0.062*
C13	0.1885 (3)	0.3001 (4)	0.4365 (2)	0.0501 (8)
H13	0.1015	0.2875	0.4243	0.060*
C14	0.2830 (2)	0.3796 (3)	0.37332 (19)	0.0432 (7)
H14	0.2469	0.4559	0.3268	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0375 (4)	0.0665 (6)	0.0769 (6)	−0.0031 (4)	0.0100 (4)	0.0018 (4)
N1	0.0347 (12)	0.0361 (14)	0.0336 (12)	−0.0010 (10)	−0.0036 (9)	0.0051 (10)
O1	0.0459 (12)	0.0553 (14)	0.0429 (11)	0.0061 (10)	−0.0086 (9)	0.0132 (10)
O2	0.0503 (12)	0.0730 (16)	0.0430 (12)	0.0006 (11)	−0.0072 (9)	0.0236 (11)
O3	0.0454 (11)	0.0324 (11)	0.0551 (12)	−0.0050 (9)	−0.0040 (9)	−0.0061 (9)
C1	0.0467 (16)	0.0283 (16)	0.0354 (14)	0.0026 (13)	−0.0017 (12)	0.0011 (12)
C2	0.0396 (15)	0.0312 (15)	0.0376 (14)	−0.0008 (12)	0.0009 (12)	0.0058 (12)
C3	0.0364 (15)	0.0312 (15)	0.0380 (14)	−0.0059 (12)	−0.0040 (11)	0.0003 (12)
C4	0.0413 (16)	0.0339 (16)	0.0351 (15)	−0.0025 (13)	−0.0059 (12)	−0.0018 (13)
C5	0.0348 (14)	0.0275 (15)	0.0351 (14)	0.0032 (11)	−0.0015 (11)	0.0025 (11)
C6	0.0389 (15)	0.0378 (17)	0.0362 (15)	−0.0007 (13)	−0.0059 (12)	−0.0006 (13)
C7	0.0443 (16)	0.0386 (17)	0.0364 (15)	0.0044 (14)	0.0039 (12)	−0.0004 (13)
C8	0.0340 (15)	0.0359 (17)	0.0521 (18)	0.0043 (13)	0.0035 (13)	0.0038 (14)
C9	0.0344 (15)	0.0430 (18)	0.0516 (18)	−0.0021 (13)	−0.0069 (13)	−0.0070 (14)
C10	0.0423 (15)	0.0387 (17)	0.0330 (14)	0.0028 (13)	−0.0018 (12)	−0.0036 (12)
C11	0.0461 (17)	0.0462 (18)	0.0355 (15)	−0.0017 (14)	−0.0021 (12)	0.0004 (13)
C12	0.0538 (19)	0.050 (2)	0.0523 (18)	−0.0059 (16)	0.0158 (15)	−0.0042 (16)
C13	0.0371 (16)	0.049 (2)	0.065 (2)	−0.0053 (14)	0.0093 (15)	−0.0124 (16)
C14	0.0392 (15)	0.0390 (17)	0.0510 (17)	0.0016 (14)	−0.0083 (13)	−0.0028 (14)

Cl1—C8	1.740 (3)	C5—C6	1.382 (3)
N1—C4	1.392 (3)	C6—C7	1.380 (3)
N1—C1	1.400 (3)	C6—H6	0.9300
N1—C5	1.432 (3)	C7—C8	1.369 (4)
O1—C1	1.199 (3)	C7—H7	0.9300
O2—C4	1.204 (3)	C8—C9	1.378 (4)
O3—C11	1.431 (3)	C9—C10	1.376 (4)
O3—C14	1.440 (3)	C9—H9	0.9300
C1—C2	1.496 (4)	C10—H10	0.9300
C2—C3	1.533 (3)	C11—C12	1.508 (4)
C2—C11	1.563 (4)	C11—H11	0.9800
C2—H2	0.9800	C12—C13	1.313 (4)
C3—C4	1.505 (4)	C12—H12	0.9300
C3—C14	1.547 (4)	C13—C14	1.503 (4)
C3—H3	0.9800	C13—H13	0.9300
C5—C10	1.380 (3)	C14—H14	0.9800
C4—N1—C1	112.4 (2)	C8—C7—H7	120.4
C4—N1—C5	123.6 (2)	C6—C7—H7	120.4
C1—N1—C5	123.9 (2)	C7—C8—C9	121.3 (2)
C11—O3—C14	95.76 (19)	C7—C8—Cl1	119.7 (2)
O1—C1—N1	124.2 (2)	C9—C8—Cl1	118.9 (2)
O1—C1—C2	127.6 (2)	C10—C9—C8	119.5 (3)
N1—C1—C2	108.2 (2)	C10—C9—H9	120.3
C1—C2—C3	105.7 (2)	C8—C9—H9	120.3
C1—C2—C11	112.4 (2)	C9—C10—C5	119.7 (2)
C3—C2—C11	100.1 (2)	C9—C10—H10	120.1
C1—C2—H2	112.6	C5—C10—H10	120.1
C3—C2—H2	112.6	O3—C11—C12	102.6 (2)
C11—C2—H2	112.6	O3—C11—C2	101.68 (19)
C4—C3—C2	104.6 (2)	C12—C11—C2	104.8 (2)
C4—C3—C14	110.5 (2)	O3—C11—H11	115.3
C2—C3—C14	101.9 (2)	C12—C11—H11	115.3
C4—C3—H3	113.0	C2—C11—H11	115.3
C2—C3—H3	113.0	C13—C12—C11	105.2 (3)
C14—C3—H3	113.0	C13—C12—H12	127.4
O2—C4—N1	124.4 (2)	C11—C12—H12	127.4
O2—C4—C3	126.8 (2)	C12—C13—C14	106.3 (3)
N1—C4—C3	108.8 (2)	C12—C13—H13	126.9
C10—C5—C6	120.3 (2)	C14—C13—H13	126.9
C10—C5—N1	119.4 (2)	O3—C14—C13	101.9 (2)
C6—C5—N1	120.3 (2)	O3—C14—C3	99.7 (2)
C7—C6—C5	119.9 (2)	C13—C14—C3	107.0 (2)
C7—C6—H6	120.1	O3—C14—H14	115.4
C5—C6—H6	120.1	C13—C14—H14	115.4
C8—C7—C6	119.3 (2)	C3—C14—H14	115.4
C4—N1—C1—O1	179.0 (3)	C5—C6—C7—C8	0.8 (4)
C5—N1—C1—O1	−4.8 (4)	C6—C7—C8—C9	−0.8 (4)
C4—N1—C1—C2	−1.9 (3)	C6—C7—C8—Cl1	−179.9 (2)
C5—N1—C1—C2	174.3 (2)	C7—C8—C9—C10	0.4 (4)
O1—C1—C2—C3	−176.4 (3)	Cl1—C8—C9—C10	179.5 (2)
N1—C1—C2—C3	4.5 (3)	C8—C9—C10—C5	0.2 (4)
O1—C1—C2—C11	75.3 (4)	C6—C5—C10—C9	−0.2 (4)
N1—C1—C2—C11	−103.8 (2)	N1—C5—C10—C9	−178.5 (2)
C1—C2—C3—C4	−5.3 (3)	C14—O3—C11—C12	−49.2 (2)
C11—C2—C3—C4	111.7 (2)	C14—O3—C11—C2	59.1 (2)
C1—C2—C3—C14	−120.4 (2)	C1—C2—C11—O3	78.3 (2)
C11—C2—C3—C14	−3.5 (2)	C3—C2—C11—O3	−33.5 (2)
C1—N1—C4—O2	176.7 (3)	C1—C2—C11—C12	−175.1 (2)
C5—N1—C4—O2	0.4 (4)	C3—C2—C11—C12	73.1 (2)
C1—N1—C4—C3	−1.6 (3)	O3—C11—C12—C13	31.7 (3)
C5—N1—C4—C3	−177.9 (2)	C2—C11—C12—C13	−74.2 (3)
C2—C3—C4—O2	−173.9 (3)	C11—C12—C13—C14	0.3 (3)
C14—C3—C4—O2	−65.0 (4)	C11—O3—C14—C13	49.1 (2)
C2—C3—C4—N1	4.3 (3)	C11—O3—C14—C3	−60.8 (2)
C14—C3—C4—N1	113.3 (2)	C12—C13—C14—O3	−31.9 (3)
C4—N1—C5—C10	128.6 (3)	C12—C13—C14—C3	72.3 (3)
C1—N1—C5—C10	−47.3 (4)	C4—C3—C14—O3	−71.6 (2)
C4—N1—C5—C6	−49.7 (4)	C2—C3—C14—O3	39.1 (2)
C1—N1—C5—C6	134.5 (3)	C4—C3—C14—C13	−177.4 (2)
C10—C5—C6—C7	−0.2 (4)	C2—C3—C14—C13	−66.7 (3)
N1—C5—C6—C7	178.0 (2)