4-(2-Amino-phen-yl)-10-oxa-4-aza-tricyclo-[5.2.1.0]dec-8-ene-3,5-dione.

In the title compound, C(14)H(12)N(2)O(3), the essentially planar pyrrole ring [maximum deviation = 0.037 (4) Å] and the benzene ring form a dihedral angle of 69.5 (2)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect mol-ecules into chains along [001]. Additional stabilization is provided by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the pharmacological applications of 7-oxabicyclo­[2.2.1]hept-5-ene-2,3-dicarb­oxy­lic anhydride and its derivatives, see: Deng & Hu (2007 ▶); Hart et al. (2004 ▶). For related structures, see: Li (2010a ▶,b ▶); Goh et al. (2008 ▶).

Experimental

Crystal data

C14H12N2O3

M = 256.26

Orthorhombic,

a = 10.4457 (11) Å

b = 8.8245 (9) Å

c = 13.2114 (15) Å

V = 1217.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.38 × 0.33 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.963, T max = 0.980

5021 measured reflections

1131 independent reflections

827 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.084

S = 1.01

1131 reflections

173 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100362X/lh5200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100362X/lh5200Isup2.hkl

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

C14H12N2O3	F(000) = 536
Mr = 256.26	Dx = 1.398 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 975 reflections
a = 10.4457 (11) Å	θ = 3.1–20.1°
b = 8.8245 (9) Å	µ = 0.10 mm−1
c = 13.2114 (15) Å	T = 298 K
V = 1217.8 (2) Å3	Block, pale yellow
Z = 4	0.38 × 0.33 × 0.20 mm

Bruker SMART CCD diffractometer	1131 independent reflections
Radiation source: fine-focus sealed tube	827 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→11
Tmin = 0.963, Tmax = 0.980	k = −10→10
5021 measured reflections	l = −15→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0348P)2] where P = (Fo2 + 2Fc2)/3
1131 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.12 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
N1	0.0406 (3)	0.1444 (3)	0.0863 (2)	0.0401 (7)
N2	0.2069 (3)	0.1868 (4)	0.2520 (3)	0.0729 (11)
H2A	0.2110	0.1054	0.2164	0.087*
H2B	0.2577	0.1992	0.3025	0.087*
O1	−0.0454 (3)	−0.0189 (3)	0.20351 (18)	0.0680 (9)
O2	0.1232 (3)	0.2521 (3)	−0.0577 (2)	0.0671 (9)
O3	0.2418 (2)	−0.1090 (3)	0.03190 (19)	0.0562 (7)
C1	−0.0025 (4)	0.0040 (4)	0.1192 (3)	0.0467 (9)
C2	0.0207 (4)	−0.1091 (4)	0.0363 (3)	0.0476 (9)
H2	−0.0560	−0.1684	0.0201	0.057*
C3	0.0677 (3)	−0.0159 (4)	−0.0536 (3)	0.0469 (10)
H3	0.0115	−0.0229	−0.1128	0.056*
C4	0.0818 (3)	0.1439 (5)	−0.0139 (3)	0.0462 (10)
C5	0.0363 (4)	0.2805 (4)	0.1474 (3)	0.0442 (9)
C6	0.1193 (4)	0.2968 (4)	0.2282 (3)	0.0490 (10)
C7	0.1108 (5)	0.4281 (5)	0.2857 (3)	0.0709 (14)
H7	0.1657	0.4417	0.3404	0.085*
C8	0.0224 (6)	0.5379 (5)	0.2631 (4)	0.0818 (16)
H8	0.0173	0.6247	0.3029	0.098*
C9	−0.0598 (5)	0.5204 (5)	0.1810 (4)	0.0783 (14)
H9	−0.1187	0.5958	0.1652	0.094*
C10	−0.0533 (4)	0.3914 (5)	0.1239 (3)	0.0588 (11)
H10	−0.1087	0.3780	0.0695	0.071*
C11	0.1408 (4)	−0.2123 (4)	0.0576 (3)	0.0555 (11)
H11	0.1455	−0.2562	0.1256	0.067*
C12	0.1452 (4)	−0.3243 (5)	−0.0286 (3)	0.0640 (12)
H12	0.1251	−0.4269	−0.0259	0.077*
C13	0.1827 (4)	−0.2477 (5)	−0.1075 (3)	0.0629 (13)
H13	0.1946	−0.2846	−0.1728	0.075*
C14	0.2030 (4)	−0.0868 (4)	−0.0717 (3)	0.0548 (11)
H14	0.2615	−0.0259	−0.1130	0.066*

	U11	U22	U33	U12	U13	U23
N1	0.0467 (17)	0.0387 (18)	0.0349 (15)	−0.0027 (15)	0.0028 (13)	0.0024 (14)
N2	0.076 (3)	0.068 (2)	0.075 (3)	−0.004 (2)	−0.025 (2)	0.004 (2)
O1	0.094 (2)	0.066 (2)	0.0437 (16)	−0.0215 (16)	0.0186 (16)	0.0025 (14)
O2	0.093 (2)	0.0526 (19)	0.0561 (17)	−0.0006 (16)	0.0217 (16)	0.0131 (14)
O3	0.0502 (17)	0.0539 (16)	0.0644 (17)	−0.0025 (15)	−0.0137 (14)	−0.0007 (13)
C1	0.051 (2)	0.049 (2)	0.040 (2)	−0.008 (2)	−0.0003 (18)	−0.0011 (17)
C2	0.052 (2)	0.048 (2)	0.0433 (19)	−0.009 (2)	0.0000 (18)	−0.0039 (19)
C3	0.051 (2)	0.051 (2)	0.038 (2)	0.005 (2)	−0.0063 (17)	0.0006 (18)
C4	0.047 (2)	0.050 (3)	0.042 (2)	0.006 (2)	0.0011 (18)	0.009 (2)
C5	0.046 (2)	0.042 (2)	0.045 (2)	0.002 (2)	0.0095 (18)	0.0005 (18)
C6	0.053 (3)	0.049 (2)	0.045 (2)	−0.004 (2)	0.0000 (19)	−0.0003 (19)
C7	0.086 (4)	0.065 (3)	0.062 (3)	−0.027 (3)	0.014 (2)	−0.019 (2)
C8	0.095 (4)	0.053 (3)	0.097 (4)	−0.012 (3)	0.049 (3)	−0.028 (3)
C9	0.068 (4)	0.051 (3)	0.115 (4)	0.016 (3)	0.027 (3)	0.003 (3)
C10	0.055 (3)	0.047 (2)	0.075 (3)	0.003 (2)	0.008 (2)	0.004 (2)
C11	0.067 (3)	0.050 (2)	0.050 (2)	−0.003 (2)	−0.006 (2)	0.0055 (18)
C12	0.076 (3)	0.046 (3)	0.070 (3)	0.005 (2)	0.001 (2)	−0.008 (2)
C13	0.069 (3)	0.061 (3)	0.059 (3)	0.014 (2)	0.002 (2)	−0.013 (2)
C14	0.056 (3)	0.061 (3)	0.047 (2)	0.006 (2)	0.0046 (19)	0.003 (2)

N1—C1	1.388 (4)	C5—C6	1.383 (5)
N1—C4	1.392 (4)	C5—C10	1.390 (5)
N1—C5	1.447 (4)	C6—C7	1.388 (5)
N2—C6	1.370 (5)	C7—C8	1.372 (7)
N2—H2A	0.8600	C7—H7	0.9300
N2—H2B	0.8600	C8—C9	1.392 (7)
O1—C1	1.217 (4)	C8—H8	0.9300
O2—C4	1.198 (4)	C9—C10	1.367 (6)
O3—C11	1.434 (4)	C9—H9	0.9300
O3—C14	1.440 (4)	C10—H10	0.9300
C1—C2	1.502 (5)	C11—C12	1.508 (5)
C2—C3	1.525 (5)	C11—H11	0.9800
C2—C11	1.576 (5)	C12—C13	1.303 (6)
C2—H2	0.9800	C12—H12	0.9300
C3—C4	1.512 (5)	C13—C14	1.512 (5)
C3—C14	1.564 (5)	C13—H13	0.9300
C3—H3	0.9800	C14—H14	0.9800
C1—N1—C4	113.3 (3)	C8—C7—C6	120.9 (5)
C1—N1—C5	123.8 (3)	C8—C7—H7	119.5
C4—N1—C5	122.9 (3)	C6—C7—H7	119.5
C6—N2—H2A	120.0	C7—C8—C9	120.4 (4)
C6—N2—H2B	120.0	C7—C8—H8	119.8
H2A—N2—H2B	120.0	C9—C8—H8	119.8
C11—O3—C14	96.0 (3)	C10—C9—C8	119.5 (4)
O1—C1—N1	123.6 (3)	C10—C9—H9	120.3
O1—C1—C2	128.1 (4)	C8—C9—H9	120.3
N1—C1—C2	108.2 (3)	C9—C10—C5	119.8 (4)
C1—C2—C3	105.2 (3)	C9—C10—H10	120.1
C1—C2—C11	112.4 (3)	C5—C10—H10	120.1
C3—C2—C11	101.2 (3)	O3—C11—C12	102.5 (3)
C1—C2—H2	112.4	O3—C11—C2	100.2 (3)
C3—C2—H2	112.4	C12—C11—C2	105.5 (3)
C11—C2—H2	112.4	O3—C11—H11	115.6
C4—C3—C2	105.3 (3)	C12—C11—H11	115.6
C4—C3—C14	109.8 (3)	C2—C11—H11	115.6
C2—C3—C14	101.2 (3)	C13—C12—C11	105.9 (4)
C4—C3—H3	113.2	C13—C12—H12	127.1
C2—C3—H3	113.2	C11—C12—H12	127.1
C14—C3—H3	113.2	C12—C13—C14	106.1 (4)
O2—C4—N1	124.7 (4)	C12—C13—H13	126.9
O2—C4—C3	127.7 (4)	C14—C13—H13	126.9
N1—C4—C3	107.6 (3)	O3—C14—C13	102.1 (3)
C6—C5—C10	121.4 (3)	O3—C14—C3	99.4 (3)
C6—C5—N1	119.9 (3)	C13—C14—C3	107.3 (3)
C10—C5—N1	118.7 (3)	O3—C14—H14	115.4
N2—C6—C5	121.4 (3)	C13—C14—H14	115.4
N2—C6—C7	120.6 (4)	C3—C14—H14	115.4
C5—C6—C7	118.0 (4)
C4—N1—C1—O1	−178.2 (4)	C10—C5—C6—C7	0.0 (5)
C5—N1—C1—O1	−1.7 (5)	N1—C5—C6—C7	−179.1 (3)
C4—N1—C1—C2	4.9 (4)	N2—C6—C7—C8	−179.2 (4)
C5—N1—C1—C2	−178.6 (3)	C5—C6—C7—C8	0.1 (6)
O1—C1—C2—C3	176.8 (4)	C6—C7—C8—C9	−0.7 (7)
N1—C1—C2—C3	−6.4 (4)	C7—C8—C9—C10	1.1 (7)
O1—C1—C2—C11	−73.9 (5)	C8—C9—C10—C5	−0.9 (6)
N1—C1—C2—C11	102.8 (3)	C6—C5—C10—C9	0.4 (6)
C1—C2—C3—C4	5.6 (4)	N1—C5—C10—C9	179.5 (3)
C11—C2—C3—C4	−111.6 (3)	C14—O3—C11—C12	48.6 (3)
C1—C2—C3—C14	119.9 (3)	C14—O3—C11—C2	−59.9 (3)
C11—C2—C3—C14	2.7 (3)	C1—C2—C11—O3	−77.4 (3)
C1—N1—C4—O2	−179.7 (4)	C3—C2—C11—O3	34.3 (3)
C5—N1—C4—O2	3.7 (6)	C1—C2—C11—C12	176.5 (3)
C1—N1—C4—C3	−1.1 (4)	C3—C2—C11—C12	−71.8 (4)
C5—N1—C4—C3	−177.7 (3)	O3—C11—C12—C13	−31.7 (4)
C2—C3—C4—O2	175.5 (4)	C2—C11—C12—C13	72.7 (4)
C14—C3—C4—O2	67.3 (5)	C11—C12—C13—C14	0.3 (5)
C2—C3—C4—N1	−3.0 (4)	C11—O3—C14—C13	−48.3 (3)
C14—C3—C4—N1	−111.2 (3)	C11—O3—C14—C3	61.8 (3)
C1—N1—C5—C6	72.1 (4)	C12—C13—C14—O3	31.1 (4)
C4—N1—C5—C6	−111.7 (4)	C12—C13—C14—C3	−72.9 (4)
C1—N1—C5—C10	−107.0 (4)	C4—C3—C14—O3	72.1 (3)
C4—N1—C5—C10	69.2 (5)	C2—C3—C14—O3	−38.9 (3)
C10—C5—C6—N2	179.4 (3)	C4—C3—C14—C13	178.0 (3)
N1—C5—C6—N2	0.3 (5)	C2—C3—C14—C13	67.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2i	0.86	2.28	3.131 (5)	174
C3—H3···O1ii	0.98	2.48	3.232 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2i	0.86	2.28	3.131 (5)	174
C3—H3⋯O1ii	0.98	2.48	3.232 (5)	133

Symmetry codes: (i) ; (ii) .