Ethyl 4-(2,5-dioxo-2,5-di­hydro-1H-pyrrol-1-yl)­benzoate

In the title compound, C₁₃H₁₁NO₄, the dihedral angle between the benzene and male­imide rings is 41.4 (1)°. There are C—H...O hydrogen-bonded chains, running along the a and c axes.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.138
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin, 1993); software used to prepare material for publication: PLATON (Spek, 1990).

Ethyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate

Crystal data

C13H11NO4	F(000) = 512
Mr = 245.23	Dx = 1.365 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 775 reflections
a = 12.028 (6) Å	θ = 2.2–25.5°
b = 7.358 (4) Å	µ = 0.10 mm^−1
c = 13.561 (7) Å	T = 293 K
β = 96.364 (7)°	Prism, pale yellow
V = 1192.9 (11) Å^3	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2328 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
Tmin = 0.903, Tmax = 0.980	k = −9→9
8371 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	All H-atom parameters refined
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0933P)^2 + 0.1715P] where P = (Fo^2 + 2Fc^2)/3
2328 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.38443 (10)	0.3350 (2)	0.49702 (10)	0.0737 (4)
O2	0.51187 (12)	−0.0551 (3)	0.74371 (13)	0.1025 (6)
O3	−0.11005 (9)	0.0763 (2)	0.65990 (9)	0.0694 (4)
O4	−0.04247 (8)	0.10226 (16)	0.82013 (8)	0.0541 (3)
N1	0.41506 (9)	0.12811 (15)	0.62585 (8)	0.0403 (3)
C1	0.44679 (12)	0.2432 (2)	0.55179 (10)	0.0486 (4)
C2	0.56988 (13)	0.2254 (2)	0.55475 (13)	0.0594 (4)
C3	0.60637 (14)	0.1140 (3)	0.62521 (14)	0.0605 (5)
C4	0.51060 (13)	0.0471 (2)	0.67553 (12)	0.0563 (4)
C5	0.30424 (11)	0.11369 (17)	0.65244 (10)	0.0379 (3)
C6	0.21556 (12)	0.1047 (2)	0.57787 (11)	0.0451 (3)
C7	0.10794 (12)	0.0986 (2)	0.60345 (11)	0.0472 (4)
C8	0.08690 (11)	0.09822 (18)	0.70209 (11)	0.0425 (3)
C9	0.17659 (12)	0.1051 (2)	0.77632 (11)	0.0458 (4)
C10	0.28494 (12)	0.1133 (2)	0.75209 (11)	0.0444 (3)
C11	−0.03175 (12)	0.0909 (2)	0.72345 (12)	0.0469 (4)
C12	−0.15584 (12)	0.0953 (2)	0.84737 (13)	0.0535 (4)
C13	−0.14843 (16)	0.0956 (3)	0.95780 (15)	0.0651 (5)
H2	0.6094 (16)	0.294 (3)	0.5083 (14)	0.072 (5)*
H3	0.680 (2)	0.076 (3)	0.6454 (17)	0.089 (7)*
H6	0.2281 (13)	0.101 (2)	0.5105 (13)	0.048 (4)*
H7	0.0459 (16)	0.099 (2)	0.5507 (14)	0.059 (5)*
H9	0.1658 (15)	0.103 (2)	0.8425 (14)	0.062 (5)*
H10	0.3469 (15)	0.121 (2)	0.8059 (13)	0.057 (5)*
H12A	−0.1893 (15)	−0.017 (3)	0.8187 (13)	0.063 (5)*
H12B	−0.1959 (17)	0.203 (3)	0.8166 (14)	0.073 (5)*
H13A	−0.1037 (18)	−0.006 (3)	0.9867 (15)	0.081 (6)*
H13B	−0.222 (2)	0.082 (3)	0.9782 (16)	0.085 (6)*
H13C	−0.1213 (19)	0.208 (4)	0.9864 (17)	0.091 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0585 (7)	0.0896 (9)	0.0738 (8)	0.0032 (6)	0.0103 (6)	0.0366 (7)
O2	0.0682 (9)	0.1375 (14)	0.1066 (11)	0.0470 (9)	0.0304 (8)	0.0711 (11)
O3	0.0357 (6)	0.1079 (10)	0.0635 (7)	−0.0071 (6)	0.0005 (5)	0.0064 (6)
O4	0.0337 (5)	0.0721 (7)	0.0579 (7)	−0.0051 (4)	0.0117 (4)	−0.0011 (5)
N1	0.0340 (6)	0.0471 (6)	0.0403 (6)	0.0012 (4)	0.0070 (4)	0.0016 (4)
C1	0.0439 (8)	0.0536 (8)	0.0494 (8)	−0.0031 (6)	0.0103 (6)	0.0043 (6)
C2	0.0432 (8)	0.0701 (10)	0.0679 (10)	−0.0077 (7)	0.0188 (7)	0.0006 (8)
C3	0.0355 (8)	0.0826 (12)	0.0649 (10)	0.0064 (7)	0.0117 (7)	−0.0057 (8)
C4	0.0421 (8)	0.0716 (10)	0.0566 (9)	0.0174 (7)	0.0113 (6)	0.0109 (8)
C5	0.0343 (7)	0.0388 (6)	0.0410 (7)	0.0001 (5)	0.0065 (5)	−0.0003 (5)
C6	0.0426 (8)	0.0545 (8)	0.0385 (7)	−0.0044 (6)	0.0053 (6)	−0.0047 (6)
C7	0.0362 (7)	0.0578 (9)	0.0461 (8)	−0.0056 (6)	−0.0020 (6)	−0.0040 (6)
C8	0.0350 (7)	0.0433 (7)	0.0497 (8)	−0.0034 (5)	0.0066 (6)	0.0013 (5)
C9	0.0396 (8)	0.0594 (9)	0.0389 (7)	−0.0007 (6)	0.0068 (6)	0.0038 (6)
C10	0.0353 (7)	0.0584 (8)	0.0391 (7)	−0.0007 (6)	0.0023 (5)	0.0032 (6)
C11	0.0361 (8)	0.0490 (8)	0.0558 (9)	−0.0031 (6)	0.0056 (6)	0.0043 (6)
C12	0.0324 (7)	0.0584 (10)	0.0716 (10)	−0.0015 (6)	0.0141 (7)	−0.0004 (8)
C13	0.0483 (10)	0.0785 (13)	0.0722 (11)	−0.0019 (9)	0.0230 (8)	−0.0055 (9)

Geometric parameters (Å, º)

N1—C4	1.3994 (19)	C10—C9	1.380 (2)
N1—C1	1.3989 (18)	C10—H10	0.986 (18)
N1—C5	1.4230 (17)	C9—H9	0.921 (19)
O4—C11	1.334 (2)	C6—H6	0.943 (17)
O4—C12	1.4528 (18)	C1—C2	1.482 (2)
O3—C11	1.209 (2)	C3—C2	1.298 (3)
O2—C4	1.191 (2)	C3—C4	1.486 (2)
O1—C1	1.2030 (19)	C3—H3	0.94 (2)
C5—C6	1.388 (2)	C12—C13	1.490 (3)
C5—C10	1.396 (2)	C12—H12A	0.98 (2)
C7—C6	1.377 (2)	C12—H12B	1.00 (2)
C7—C8	1.389 (2)	C2—H2	0.97 (2)
C7—H7	0.974 (19)	C13—H13A	0.98 (2)
C8—C9	1.392 (2)	C13—H13C	0.96 (3)
C8—C11	1.488 (2)	C13—H13B	0.97 (2)
C4—N1—C1	109.20 (12)	O1—C1—N1	125.61 (13)
C4—N1—C5	126.06 (12)	O1—C1—C2	128.23 (14)
C1—N1—C5	124.39 (11)	N1—C1—C2	106.15 (13)
C11—O4—C12	116.32 (12)	C2—C3—C4	109.34 (15)
C6—C5—C10	120.55 (13)	C2—C3—H3	129.4 (14)
C6—C5—N1	119.01 (12)	C4—C3—H3	121.2 (14)
C10—C5—N1	120.42 (12)	O2—C4—N1	125.60 (15)
C6—C7—C8	121.29 (13)	O2—C4—C3	128.46 (15)
C6—C7—H7	118.6 (11)	N1—C4—C3	105.94 (14)
C8—C7—H7	120.0 (11)	O4—C12—C13	107.59 (13)
C7—C8—C9	119.14 (13)	O4—C12—H12A	106.5 (10)
C7—C8—C11	117.95 (13)	C13—C12—H12A	112.0 (10)
C9—C8—C11	122.91 (14)	O4—C12—H12B	106.8 (11)
O3—C11—O4	123.62 (14)	C13—C12—H12B	113.1 (11)
O3—C11—C8	123.54 (15)	H12A—C12—H12B	110.4 (16)
O4—C11—C8	112.84 (12)	C3—C2—C1	109.32 (14)
C9—C10—C5	119.55 (13)	C3—C2—H2	130.9 (12)
C9—C10—H10	118.9 (10)	C1—C2—H2	119.8 (12)
C5—C10—H10	121.6 (10)	C12—C13—H13A	111.8 (12)
C10—C9—C8	120.38 (14)	C12—C13—H13C	112.9 (14)
C10—C9—H9	118.1 (11)	H13A—C13—H13C	110.4 (19)
C8—C9—H9	121.5 (11)	C12—C13—H13B	109.5 (13)
C7—C6—C5	119.08 (13)	H13A—C13—H13B	106.7 (17)
C7—C6—H6	120.0 (10)	H13C—C13—H13B	105.1 (18)
C5—C6—H6	121.0 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3^i	0.94 (2)	2.51 (2)	3.402 (3)	158 (2)
C10—H10···O1^ii	0.98 (2)	2.61 (2)	3.426 (3)	141 (1)

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2.