N-(4-Acetyl­phenyl)­maleamic acid

The structure of the title compound, C₁₂H₁₁NO₄, comprises an essentially flat mol­ecule displaying a typical maleic acid intramolecular hydrogen bond. An intermolecular N—H...O association exists from the amide to the carboxyl­ic acid carbonyl O atom, while several C—H...O close contacts are observed around the maleamic acid O atoms.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.133
• Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.48
         From the CIF: _reflns_number_total               2227
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2421
         Completeness (_total/calc)             91.99%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

N-(4-Acetylphenyl)maleamic acid

Crystal data

C12H11NO4	Dx = 1.471 Mg m^−3
Mr = 233.22	Melting point: 471-473 K K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.5577 (3) Å	Cell parameters from 6037 reflections
b = 25.5016 (14) Å	θ = 1.0–27.5°
c = 7.4588 (5) Å	µ = 0.11 mm^−1
β = 95.134 (2)°	T = 150 K
V = 1052.90 (11) Å^3	Block, yellow
Z = 4	0.10 × 0.10 × 0.10 mm
F(000) = 488

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer	2227 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1479 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 1.6°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −32→33
Tmin = 0.989, Tmax = 0.989	l = −9→9
5131 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0649P)^2 + 0.0474P] where P = (Fo^2 + 2Fc^2)/3
2227 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	−0.4467 (3)	0.41047 (7)	−0.2537 (2)	0.0186 (5)
C2	−0.2668 (3)	0.44469 (8)	−0.1820 (3)	0.0226 (5)
H2	−0.1165	0.4315	−0.1305	0.028*
C3	−0.3105 (3)	0.49801 (8)	−0.1870 (2)	0.0223 (5)
H3	−0.1871	0.5213	−0.1400	0.028*
C4	−0.5292 (3)	0.51856 (8)	−0.2587 (2)	0.0193 (5)
C41	−0.5794 (4)	0.57600 (8)	−0.2649 (3)	0.0233 (5)
O41	−0.7774 (2)	0.59242 (6)	−0.32441 (19)	0.0333 (4)
C42	−0.3820 (4)	0.61270 (8)	−0.1972 (3)	0.0283 (5)
H41	−0.4403	0.6489	−0.2086	0.035*
H42	−0.2433	0.6082	−0.2681	0.035*
H43	−0.3329	0.6050	−0.0704	0.035*
C5	−0.7073 (3)	0.48380 (8)	−0.3280 (2)	0.0214 (5)
H5	−0.8588	0.4971	−0.3771	0.027*
C6	−0.6675 (3)	0.43068 (8)	−0.3266 (3)	0.0210 (5)
H6	−0.7907	0.4076	−0.3754	0.026*
N7	−0.4208 (3)	0.35512 (7)	−0.2567 (2)	0.0206 (4)
H7	−0.545 (4)	0.3412 (8)	−0.322 (3)	0.033 (6)*
C8	−0.2403 (3)	0.32578 (8)	−0.1804 (3)	0.0211 (5)
O81	−0.0586 (2)	0.34513 (5)	−0.0945 (2)	0.0317 (4)
C9	−0.2754 (3)	0.26828 (8)	−0.2048 (3)	0.0215 (5)
H9	−0.4190	0.2579	−0.2743	0.027*
C10	−0.1304 (3)	0.22950 (8)	−0.1414 (3)	0.0219 (5)
H10	−0.1870	0.1955	−0.1756	0.027*
C11	0.1028 (4)	0.22956 (8)	−0.0274 (3)	0.0231 (5)
O10	0.1872 (2)	0.18803 (6)	0.02896 (19)	0.0322 (4)
O11	0.2172 (2)	0.27380 (6)	0.01247 (19)	0.0290 (4)
H11	0.110 (5)	0.3087 (11)	−0.034 (3)	0.065 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0209 (11)	0.0152 (11)	0.0196 (11)	0.0005 (8)	0.0017 (8)	0.0010 (8)
C2	0.0164 (10)	0.0234 (12)	0.0273 (11)	0.0008 (9)	−0.0029 (8)	−0.0010 (9)
C3	0.0205 (11)	0.0192 (11)	0.0266 (11)	−0.0013 (9)	−0.0005 (8)	−0.0017 (9)
C4	0.0208 (11)	0.0187 (11)	0.0186 (10)	0.0011 (9)	0.0031 (8)	−0.0001 (8)
C41	0.0256 (12)	0.0219 (12)	0.0225 (11)	0.0027 (9)	0.0036 (9)	−0.0005 (9)
O41	0.0280 (9)	0.0233 (9)	0.0472 (10)	0.0054 (7)	−0.0049 (7)	0.0015 (7)
C42	0.0302 (12)	0.0189 (12)	0.0350 (13)	0.0005 (9)	−0.0008 (9)	−0.0019 (9)
C5	0.0178 (10)	0.0232 (12)	0.0225 (11)	0.0012 (9)	−0.0017 (8)	0.0017 (9)
C6	0.0181 (10)	0.0202 (12)	0.0239 (11)	−0.0013 (9)	−0.0022 (8)	0.0004 (9)
N7	0.0181 (9)	0.0171 (10)	0.0253 (10)	0.0011 (7)	−0.0050 (7)	−0.0002 (7)
C8	0.0199 (11)	0.0201 (11)	0.0231 (11)	−0.0004 (9)	0.0003 (8)	0.0000 (9)
O81	0.0261 (8)	0.0194 (8)	0.0461 (10)	0.0011 (6)	−0.0150 (7)	−0.0031 (7)
C9	0.0210 (11)	0.0193 (11)	0.0235 (11)	−0.0002 (9)	−0.0020 (8)	−0.0026 (9)
C10	0.0230 (11)	0.0202 (11)	0.0221 (11)	−0.0002 (9)	0.0002 (8)	0.0011 (9)
C11	0.0246 (12)	0.0209 (12)	0.0236 (11)	0.0005 (9)	0.0013 (8)	−0.0026 (9)
O10	0.0321 (9)	0.0199 (9)	0.0418 (10)	0.0056 (7)	−0.0124 (7)	0.0016 (7)
O11	0.0228 (8)	0.0195 (9)	0.0422 (9)	0.0000 (6)	−0.0100 (6)	−0.0004 (7)

Geometric parameters (Å, º)

C1—C6	1.396 (3)	C5—H5	0.95
C1—C2	1.397 (3)	C6—H6	0.95
C1—N7	1.419 (2)	N7—C8	1.337 (2)
C2—C3	1.381 (3)	N7—H7	0.88 (2)
C2—H2	0.95	C8—O81	1.248 (2)
C3—C4	1.386 (3)	C8—C9	1.488 (3)
C3—H3	0.95	O81—H11	1.37 (3)
C4—C5	1.393 (3)	C9—C10	1.335 (3)
C4—C41	1.491 (3)	C9—H9	0.95
C41—O41	1.223 (2)	C10—C11	1.485 (3)
C41—C42	1.495 (3)	C10—H10	0.95
C42—H41	0.98	C11—O10	1.218 (2)
C42—H42	0.98	C11—O11	1.316 (2)
C42—H43	0.98	O11—H11	1.11 (3)
C5—C6	1.372 (3)
C6—C1—C2	119.51 (18)	C6—C5—H5	119.4
C6—C1—N7	116.60 (17)	C4—C5—H5	119.4
C2—C1—N7	123.88 (17)	C5—C6—C1	120.17 (18)
C3—C2—C1	119.14 (17)	C5—C6—H6	119.9
C3—C2—H2	120.4	C1—C6—H6	119.9
C1—C2—H2	120.4	C8—N7—C1	128.53 (17)
C2—C3—C4	121.90 (18)	C8—N7—H7	121.9 (14)
C2—C3—H3	119.1	C1—N7—H7	109.6 (14)
C4—C3—H3	119.1	O81—C8—N7	122.62 (19)
C3—C4—C5	118.15 (18)	O81—C8—C9	122.93 (17)
C3—C4—C41	122.58 (18)	N7—C8—C9	114.45 (16)
C5—C4—C41	119.28 (16)	C8—O81—H11	113.6 (11)
O41—C41—C4	120.48 (18)	C10—C9—C8	128.15 (18)
O41—C41—C42	121.17 (19)	C10—C9—H9	115.9
C4—C41—C42	118.35 (17)	C8—C9—H9	115.9
C41—C42—H41	109.5	C9—C10—C11	132.10 (19)
C41—C42—H42	109.5	C9—C10—H10	114.0
H41—C42—H42	109.5	C11—C10—H10	114.0
C41—C42—H43	109.5	O10—C11—O11	120.27 (19)
H41—C42—H43	109.5	O10—C11—C10	119.09 (19)
H42—C42—H43	109.5	O11—C11—C10	120.64 (18)
C6—C5—C4	121.12 (17)	C11—O11—H11	112.5 (13)
C6—C1—C2—C3	−0.9 (3)	C2—C1—C6—C5	0.1 (3)
N7—C1—C2—C3	179.62 (17)	N7—C1—C6—C5	179.68 (16)
C1—C2—C3—C4	1.0 (3)	C6—C1—N7—C8	−172.53 (18)
C2—C3—C4—C5	−0.4 (3)	C2—C1—N7—C8	7.0 (3)
C2—C3—C4—C41	179.90 (18)	C1—N7—C8—O81	−1.5 (3)
C3—C4—C41—O41	−177.79 (17)	C1—N7—C8—C9	177.90 (17)
C5—C4—C41—O41	2.5 (3)	O81—C8—C9—C10	1.0 (3)
C3—C4—C41—C42	2.4 (3)	N7—C8—C9—C10	−178.39 (19)
C5—C4—C41—C42	−177.35 (16)	C8—C9—C10—C11	1.2 (4)
C3—C4—C5—C6	−0.4 (3)	C9—C10—C11—O10	171.9 (2)
C41—C4—C5—C6	179.34 (17)	C9—C10—C11—O11	−8.1 (3)
C4—C5—C6—C1	0.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O10^i	0.88 (2)	1.93 (2)	2.809 (2)	178 (2)
O11—H11···O81	1.11 (3)	1.37 (3)	2.465 (2)	169 (2)
C2—H2···O81	0.95	2.24	2.842 (2)	121
C6—H6···O10^i	0.95	2.54	3.289 (2)	136
C9—H9···O11^i	0.95	2.59	3.533 (2)	174

Symmetry code: (i) x−1, −y+1/2, z−1/2.