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The structure of the title compound, C
12H
11NO
4, 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.
Supporting information
CCDC reference: 189405
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, yellow |
Z = 4 | 0.10 × 0.10 × 0.10 mm |
F(000) = 488 | |
Data collection top
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 top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0649P)2 + 0.0474P] where P = (Fo2 + 2Fc2)/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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O10i | 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···O10i | 0.95 | 2.54 | 3.289 (2) | 136 |
C9—H9···O11i | 0.95 | 2.59 | 3.533 (2) | 174 |
Symmetry code: (i) x−1, −y+1/2, z−1/2. |
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