organic compounds
3-(Phenylcarbamoyl)acrylic acid
aTianmu College of ZheJiang A & F University, Lin'An 311300, People's Republic of China
*Correspondence e-mail: shouwenjin@yahoo.cn
In the title compound, C10H9NO3, the dihedral angle between the phenyl ring and the amide group is 10.8 (2)°. The C=O and O—H bonds of the carboxyl group adopt an anti orientation and an intramolecular O—H⋯O hydrogen bond closes an S(7) ring. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(7) chains propagating in [101]. The packing is consolidated by C—H⋯O interactions, generating sheets aligned at an angle of ca 60° with the bc plane.
Related literature
For background to carboxylic acids in supramolecular chemistry, see: Grossel et al. (2006). For a related structure, see: Jin et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); 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.
Supporting information
10.1107/S1600536812035581/hb6935sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035581/hb6935Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035581/hb6935Isup3.cml
Crystals of 3-phenylcarbamoyl-acrylic acid were formed by slow evaporation of its methanol solution at room temperature. 3-phenylcarbamoyl-acrylic acid (19.1 mg, 0.10 mmol) was dissolved in 4 ml of methanol, and 2-methylquinoline (14.3 mg, 0.1 mmol) was added to the methanol solution. The solution was then filtered into a test tube and left standing at room temperature. After about one week colorless blocks crystals were obtained.
H atoms bonded to O, and N atoms were located in a difference Fourier map and refined isotropically.
Other H atoms were positioned geometrically with C—H = 0.93 Å for aromatic, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).Fig. 1. The structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. Fig. 2. Two-dimensional sheet structure formed through hydrogen bonds. |
C10H9NO3 | Z = 4 |
Mr = 191.18 | F(000) = 400 |
Monoclinic, P21/n | Dx = 1.425 Mg m−3 |
a = 7.2396 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5918 (11) Å | µ = 0.11 mm−1 |
c = 11.7718 (15) Å | T = 298 K |
β = 99.122 (1)° | BLOCK, colorless |
V = 891.25 (18) Å3 | 0.38 × 0.36 × 0.33 mm |
Bruker SMART CCD diffractometer | 2190 independent reflections |
Radiation source: fine-focus sealed tube | 1356 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
phi and ω scans | θmax = 28.3°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
Tmin = 0.960, Tmax = 0.965 | k = −14→8 |
5497 measured reflections | l = −15→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0804P)2 + 0.0617P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2190 reflections | Δρmax = 0.20 e Å−3 |
128 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (5) |
C10H9NO3 | V = 891.25 (18) Å3 |
Mr = 191.18 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2396 (8) Å | µ = 0.11 mm−1 |
b = 10.5918 (11) Å | T = 298 K |
c = 11.7718 (15) Å | 0.38 × 0.36 × 0.33 mm |
β = 99.122 (1)° |
Bruker SMART CCD diffractometer | 2190 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1356 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.965 | Rint = 0.043 |
5497 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.20 e Å−3 |
2190 reflections | Δρmin = −0.26 e Å−3 |
128 parameters |
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 | ||
O1 | 1.0940 (2) | −0.19833 (13) | 0.83751 (12) | 0.0561 (5) | |
H1 | 1.0527 | −0.1373 | 0.7987 | 0.084* | |
N1 | 0.7880 (2) | 0.00622 (13) | 0.53533 (12) | 0.0340 (4) | |
H1A | 0.7299 | −0.0337 | 0.4767 | 0.041* | |
O2 | 1.0652 (2) | −0.40422 (14) | 0.83105 (12) | 0.0546 (4) | |
C4 | 0.8638 (3) | −0.06557 (17) | 0.62392 (15) | 0.0348 (4) | |
O3 | 0.9581 (2) | −0.02077 (13) | 0.71212 (13) | 0.0585 (5) | |
C3 | 0.8248 (3) | −0.20179 (16) | 0.60914 (15) | 0.0358 (4) | |
H3 | 0.7460 | −0.2246 | 0.5421 | 0.043* | |
C5 | 0.7910 (2) | 0.14022 (16) | 0.52529 (14) | 0.0326 (4) | |
C10 | 0.6725 (3) | 0.19311 (17) | 0.43353 (16) | 0.0401 (5) | |
H10 | 0.5983 | 0.1413 | 0.3811 | 0.048* | |
C6 | 0.9055 (3) | 0.21772 (18) | 0.60146 (16) | 0.0414 (5) | |
H6 | 0.9883 | 0.1831 | 0.6619 | 0.050* | |
C2 | 0.8880 (3) | −0.29664 (17) | 0.67949 (16) | 0.0395 (5) | |
H2 | 0.8378 | −0.3748 | 0.6554 | 0.047* | |
C1 | 1.0230 (3) | −0.30190 (18) | 0.78871 (16) | 0.0395 (5) | |
C9 | 0.6645 (3) | 0.32210 (18) | 0.41997 (17) | 0.0476 (5) | |
H9 | 0.5842 | 0.3573 | 0.3586 | 0.057* | |
C7 | 0.8946 (3) | 0.34771 (19) | 0.58618 (17) | 0.0487 (5) | |
H7 | 0.9698 | 0.4001 | 0.6374 | 0.058* | |
C8 | 0.7752 (3) | 0.39960 (19) | 0.49705 (18) | 0.0496 (6) | |
H8 | 0.7683 | 0.4868 | 0.4882 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0747 (11) | 0.0394 (9) | 0.0446 (9) | 0.0003 (7) | −0.0197 (7) | 0.0041 (6) |
N1 | 0.0425 (9) | 0.0265 (8) | 0.0302 (8) | −0.0006 (6) | −0.0026 (6) | −0.0013 (6) |
O2 | 0.0712 (11) | 0.0410 (9) | 0.0462 (9) | 0.0107 (7) | −0.0073 (7) | 0.0127 (7) |
C4 | 0.0423 (10) | 0.0309 (10) | 0.0290 (9) | 0.0009 (8) | −0.0007 (7) | −0.0001 (7) |
O3 | 0.0913 (12) | 0.0311 (8) | 0.0420 (8) | −0.0062 (7) | −0.0235 (7) | 0.0000 (6) |
C3 | 0.0426 (10) | 0.0298 (10) | 0.0324 (9) | −0.0020 (8) | −0.0023 (7) | −0.0014 (7) |
C5 | 0.0402 (10) | 0.0272 (9) | 0.0298 (9) | 0.0003 (7) | 0.0043 (7) | 0.0001 (7) |
C10 | 0.0482 (11) | 0.0320 (10) | 0.0367 (10) | −0.0003 (8) | −0.0038 (8) | 0.0016 (8) |
C6 | 0.0533 (12) | 0.0332 (11) | 0.0346 (10) | −0.0037 (8) | −0.0022 (8) | 0.0009 (8) |
C2 | 0.0492 (12) | 0.0294 (10) | 0.0375 (10) | −0.0016 (8) | −0.0006 (8) | −0.0006 (8) |
C1 | 0.0468 (12) | 0.0357 (11) | 0.0347 (10) | 0.0038 (8) | 0.0022 (8) | 0.0047 (8) |
C9 | 0.0596 (13) | 0.0371 (11) | 0.0414 (11) | 0.0067 (10) | −0.0061 (9) | 0.0071 (9) |
C7 | 0.0679 (15) | 0.0329 (11) | 0.0420 (11) | −0.0073 (10) | −0.0018 (10) | −0.0023 (9) |
C8 | 0.0715 (15) | 0.0297 (11) | 0.0459 (12) | 0.0000 (10) | 0.0041 (11) | 0.0037 (9) |
O1—C1 | 1.305 (2) | C10—C9 | 1.376 (2) |
O1—H1 | 0.8200 | C10—H10 | 0.9300 |
N1—C4 | 1.336 (2) | C6—C7 | 1.389 (3) |
N1—C5 | 1.425 (2) | C6—H6 | 0.9300 |
N1—H1A | 0.8600 | C2—C1 | 1.488 (3) |
O2—C1 | 1.212 (2) | C2—H2 | 0.9300 |
C4—O3 | 1.243 (2) | C9—C8 | 1.382 (3) |
C4—C3 | 1.475 (2) | C9—H9 | 0.9300 |
C3—C2 | 1.336 (3) | C7—C8 | 1.365 (3) |
C3—H3 | 0.9300 | C7—H7 | 0.9300 |
C5—C10 | 1.387 (3) | C8—H8 | 0.9300 |
C5—C6 | 1.389 (3) | ||
C1—O1—H1 | 109.5 | C5—C6—H6 | 120.4 |
C4—N1—C5 | 128.47 (15) | C7—C6—H6 | 120.4 |
C4—N1—H1A | 115.8 | C3—C2—C1 | 132.65 (18) |
C5—N1—H1A | 115.8 | C3—C2—H2 | 113.7 |
O3—C4—N1 | 122.54 (17) | C1—C2—H2 | 113.7 |
O3—C4—C3 | 122.77 (17) | O2—C1—O1 | 120.98 (18) |
N1—C4—C3 | 114.68 (15) | O2—C1—C2 | 118.50 (18) |
C2—C3—C4 | 128.48 (17) | O1—C1—C2 | 120.51 (16) |
C2—C3—H3 | 115.8 | C10—C9—C8 | 120.30 (19) |
C4—C3—H3 | 115.8 | C10—C9—H9 | 119.9 |
C10—C5—C6 | 119.76 (17) | C8—C9—H9 | 119.9 |
C10—C5—N1 | 116.85 (16) | C8—C7—C6 | 120.97 (19) |
C6—C5—N1 | 123.40 (16) | C8—C7—H7 | 119.5 |
C9—C10—C5 | 120.07 (18) | C6—C7—H7 | 119.5 |
C9—C10—H10 | 120.0 | C7—C8—C9 | 119.76 (19) |
C5—C10—H10 | 120.0 | C7—C8—H8 | 120.1 |
C5—C6—C7 | 119.11 (18) | C9—C8—H8 | 120.1 |
C5—N1—C4—O3 | −3.0 (3) | N1—C5—C6—C7 | −178.30 (17) |
C5—N1—C4—C3 | 176.37 (16) | C4—C3—C2—C1 | −4.5 (4) |
O3—C4—C3—C2 | −4.1 (3) | C3—C2—C1—O2 | −174.8 (2) |
N1—C4—C3—C2 | 176.5 (2) | C3—C2—C1—O1 | 5.2 (3) |
C4—N1—C5—C10 | −168.15 (18) | C5—C10—C9—C8 | 0.4 (3) |
C4—N1—C5—C6 | 12.2 (3) | C5—C6—C7—C8 | −0.8 (3) |
C6—C5—C10—C9 | −1.9 (3) | C6—C7—C8—C9 | −0.7 (3) |
N1—C5—C10—C9 | 178.43 (17) | C10—C9—C8—C7 | 0.8 (3) |
C10—C5—C6—C7 | 2.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.82 | 1.68 | 2.4947 (19) | 175 |
N1—H1A···O2i | 0.86 | 2.04 | 2.885 (2) | 169 |
C9—H9···O3ii | 0.93 | 2.51 | 3.389 (2) | 157 |
C10—H10···O2i | 0.93 | 2.58 | 3.335 (2) | 138 |
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H9NO3 |
Mr | 191.18 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 7.2396 (8), 10.5918 (11), 11.7718 (15) |
β (°) | 99.122 (1) |
V (Å3) | 891.25 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.38 × 0.36 × 0.33 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.960, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5497, 2190, 1356 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.157, 1.03 |
No. of reflections | 2190 |
No. of parameters | 128 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.26 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.82 | 1.68 | 2.4947 (19) | 175 |
N1—H1A···O2i | 0.86 | 2.04 | 2.885 (2) | 169 |
C9—H9···O3ii | 0.93 | 2.51 | 3.389 (2) | 157 |
C10—H10···O2i | 0.93 | 2.58 | 3.335 (2) | 138 |
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Acknowledgements
We gratefully acknowledge the financial support of the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the innovation project of Zhejiang A & F University.
References
Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Grossel, C. M., Dwyer, A. N., Hursthouse, M. B. & Orton, J. B. (2006). CrystEngComm, 8, 123–128. Web of Science CrossRef CAS Google Scholar
Jin, S. W., Zhang, W. B., Liu, L., Gao, H. F., Wang, D. Q., Chen, R. P. & Xu, X. L. (2010). J. Mol. Struct. 975, 128–136. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The carboxylic acid contains the important hydrogen bonding functional group for crystal engineering (Grossel et al., 2006). As an extension of our study concentrating on hydrogen bonded assembly of organic acid and organic base (Jin et al., 2010), herein we report the crystal structure of 3-phenylcarbamoyl-acrylic acid.
The single-crystal of the title compound (Fig.1) with the formula C10H9NO3 was obtained by recrystallization of 3-phenylcarbamoyl-acrylic acid and 2-methylquinoline from a methanol solution. However the 2-methylquinoline molecules do not appear in the title compound. X-ray diffraction analysis indicated that the asymmetric unit of the structure contains one molecule. The conformations of the amide oxygen and the carbonyl oxygen of the acid segments are anti to each other and the amide oxygen is anti to the H atom on the olefinic group, while the carbonyl oxygen of the acid is syn to the CH at the olefinic group. Thus there existed intramolecular O—H···O hydrogen bond producing a S11(7) ring.
The dihedral angle between the phenyl ring and the amide group in the molecule is 10.8 (2)°.
Two adjacent 3-phenylcarbamoyl-acrylic acids were joined together via the N—H···O, and CH—O interactions to form a dimer. Both carboxylic acids in the dimer were almost perpendicular with each other. In the dimer there are hydrogen-bonded ring motifs with descriptors of R21(6), and R22(8). The two ring motifs were fused together by the N—H···O hydrogen bond. The neighboring carboxylic dimers were linked together through the CH—O associations between the benzene CH and the carbonyl group with C—O distance of 3.389 Å to form one-dimensional chain. The one-dimensional chains were combined together by the interchain CH—O, and N—H···O interactions to form two-dimensional sheet extending at the direction that made a dihedral angle of ca 60° with the bc plane (Fig. 2). Two two-dimensional sheets were further held together by the intersheet C–π interactions with C···Cg distance of 3.369 Å to generate two-dimensional double sheet structure.