organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 10 August 2012; accepted 13 August 2012; online 23 August 2012)

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[Grossel, C. M., Dwyer, A. N., Hursthouse, M. B. & Orton, J. B. (2006). CrystEngComm, 8, 123-128.]). For a related structure, see: Jin et al. (2010[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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9NO3

  • Mr = 191.18

  • Monoclinic, P 21 /n

  • a = 7.2396 (8) Å

  • b = 10.5918 (11) Å

  • c = 11.7718 (15) Å

  • β = 99.122 (1)°

  • V = 891.25 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 298 K

  • 0.38 × 0.36 × 0.33 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.965

  • 5497 measured reflections

  • 2190 independent reflections

  • 1356 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.157

  • S = 1.03

  • 2190 reflections

  • 128 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

For background to carboxylic acids in supramolecular chemistry, see: Grossel et al. (2006). For a related structure, see: Jin et al. (2010).

Experimental top

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.

Refinement top

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).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: 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).

Figures top
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.
3-(Phenylcarbamoyl)acrylic acid top
Crystal data top
C10H9NO3Z = 4
Mr = 191.18F(000) = 400
Monoclinic, P21/nDx = 1.425 Mg m3
a = 7.2396 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.5918 (11) ŵ = 0.11 mm1
c = 11.7718 (15) ÅT = 298 K
β = 99.122 (1)°BLOCK, colorless
V = 891.25 (18) Å30.38 × 0.36 × 0.33 mm
Data collection top
Bruker SMART CCD
diffractometer
2190 independent reflections
Radiation source: fine-focus sealed tube1356 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
phi and ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 99
Tmin = 0.960, Tmax = 0.965k = 148
5497 measured reflectionsl = 1514
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-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 reflectionsΔρmax = 0.20 e Å3
128 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (5)
Crystal data top
C10H9NO3V = 891.25 (18) Å3
Mr = 191.18Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.2396 (8) ŵ = 0.11 mm1
b = 10.5918 (11) ÅT = 298 K
c = 11.7718 (15) Å0.38 × 0.36 × 0.33 mm
β = 99.122 (1)°
Data collection top
Bruker SMART CCD
diffractometer
2190 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1356 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.965Rint = 0.043
5497 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 1.03Δρmax = 0.20 e Å3
2190 reflectionsΔρmin = 0.26 e Å3
128 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O11.0940 (2)0.19833 (13)0.83751 (12)0.0561 (5)
H11.05270.13730.79870.084*
N10.7880 (2)0.00622 (13)0.53533 (12)0.0340 (4)
H1A0.72990.03370.47670.041*
O21.0652 (2)0.40422 (14)0.83105 (12)0.0546 (4)
C40.8638 (3)0.06557 (17)0.62392 (15)0.0348 (4)
O30.9581 (2)0.02077 (13)0.71212 (13)0.0585 (5)
C30.8248 (3)0.20179 (16)0.60914 (15)0.0358 (4)
H30.74600.22460.54210.043*
C50.7910 (2)0.14022 (16)0.52529 (14)0.0326 (4)
C100.6725 (3)0.19311 (17)0.43353 (16)0.0401 (5)
H100.59830.14130.38110.048*
C60.9055 (3)0.21772 (18)0.60146 (16)0.0414 (5)
H60.98830.18310.66190.050*
C20.8880 (3)0.29664 (17)0.67949 (16)0.0395 (5)
H20.83780.37480.65540.047*
C11.0230 (3)0.30190 (18)0.78871 (16)0.0395 (5)
C90.6645 (3)0.32210 (18)0.41997 (17)0.0476 (5)
H90.58420.35730.35860.057*
C70.8946 (3)0.34771 (19)0.58618 (17)0.0487 (5)
H70.96980.40010.63740.058*
C80.7752 (3)0.39960 (19)0.49705 (18)0.0496 (6)
H80.76830.48680.48820.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0747 (11)0.0394 (9)0.0446 (9)0.0003 (7)0.0197 (7)0.0041 (6)
N10.0425 (9)0.0265 (8)0.0302 (8)0.0006 (6)0.0026 (6)0.0013 (6)
O20.0712 (11)0.0410 (9)0.0462 (9)0.0107 (7)0.0073 (7)0.0127 (7)
C40.0423 (10)0.0309 (10)0.0290 (9)0.0009 (8)0.0007 (7)0.0001 (7)
O30.0913 (12)0.0311 (8)0.0420 (8)0.0062 (7)0.0235 (7)0.0000 (6)
C30.0426 (10)0.0298 (10)0.0324 (9)0.0020 (8)0.0023 (7)0.0014 (7)
C50.0402 (10)0.0272 (9)0.0298 (9)0.0003 (7)0.0043 (7)0.0001 (7)
C100.0482 (11)0.0320 (10)0.0367 (10)0.0003 (8)0.0038 (8)0.0016 (8)
C60.0533 (12)0.0332 (11)0.0346 (10)0.0037 (8)0.0022 (8)0.0009 (8)
C20.0492 (12)0.0294 (10)0.0375 (10)0.0016 (8)0.0006 (8)0.0006 (8)
C10.0468 (12)0.0357 (11)0.0347 (10)0.0038 (8)0.0022 (8)0.0047 (8)
C90.0596 (13)0.0371 (11)0.0414 (11)0.0067 (10)0.0061 (9)0.0071 (9)
C70.0679 (15)0.0329 (11)0.0420 (11)0.0073 (10)0.0018 (10)0.0023 (9)
C80.0715 (15)0.0297 (11)0.0459 (12)0.0000 (10)0.0041 (11)0.0037 (9)
Geometric parameters (Å, º) top
O1—C11.305 (2)C10—C91.376 (2)
O1—H10.8200C10—H100.9300
N1—C41.336 (2)C6—C71.389 (3)
N1—C51.425 (2)C6—H60.9300
N1—H1A0.8600C2—C11.488 (3)
O2—C11.212 (2)C2—H20.9300
C4—O31.243 (2)C9—C81.382 (3)
C4—C31.475 (2)C9—H90.9300
C3—C21.336 (3)C7—C81.365 (3)
C3—H30.9300C7—H70.9300
C5—C101.387 (3)C8—H80.9300
C5—C61.389 (3)
C1—O1—H1109.5C5—C6—H6120.4
C4—N1—C5128.47 (15)C7—C6—H6120.4
C4—N1—H1A115.8C3—C2—C1132.65 (18)
C5—N1—H1A115.8C3—C2—H2113.7
O3—C4—N1122.54 (17)C1—C2—H2113.7
O3—C4—C3122.77 (17)O2—C1—O1120.98 (18)
N1—C4—C3114.68 (15)O2—C1—C2118.50 (18)
C2—C3—C4128.48 (17)O1—C1—C2120.51 (16)
C2—C3—H3115.8C10—C9—C8120.30 (19)
C4—C3—H3115.8C10—C9—H9119.9
C10—C5—C6119.76 (17)C8—C9—H9119.9
C10—C5—N1116.85 (16)C8—C7—C6120.97 (19)
C6—C5—N1123.40 (16)C8—C7—H7119.5
C9—C10—C5120.07 (18)C6—C7—H7119.5
C9—C10—H10120.0C7—C8—C9119.76 (19)
C5—C10—H10120.0C7—C8—H8120.1
C5—C6—C7119.11 (18)C9—C8—H8120.1
C5—N1—C4—O33.0 (3)N1—C5—C6—C7178.30 (17)
C5—N1—C4—C3176.37 (16)C4—C3—C2—C14.5 (4)
O3—C4—C3—C24.1 (3)C3—C2—C1—O2174.8 (2)
N1—C4—C3—C2176.5 (2)C3—C2—C1—O15.2 (3)
C4—N1—C5—C10168.15 (18)C5—C10—C9—C80.4 (3)
C4—N1—C5—C612.2 (3)C5—C6—C7—C80.8 (3)
C6—C5—C10—C91.9 (3)C6—C7—C8—C90.7 (3)
N1—C5—C10—C9178.43 (17)C10—C9—C8—C70.8 (3)
C10—C5—C6—C72.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.821.682.4947 (19)175
N1—H1A···O2i0.862.042.885 (2)169
C9—H9···O3ii0.932.513.389 (2)157
C10—H10···O2i0.932.583.335 (2)138
Symmetry codes: (i) x1/2, y1/2, z1/2; (ii) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC10H9NO3
Mr191.18
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.2396 (8), 10.5918 (11), 11.7718 (15)
β (°) 99.122 (1)
V3)891.25 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.38 × 0.36 × 0.33
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.960, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
5497, 2190, 1356
Rint0.043
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.157, 1.03
No. of reflections2190
No. of parameters128
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.26

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.821.682.4947 (19)175
N1—H1A···O2i0.862.042.885 (2)169
C9—H9···O3ii0.932.513.389 (2)157
C10—H10···O2i0.932.583.335 (2)138
Symmetry codes: (i) x1/2, y1/2, z1/2; (ii) x1/2, y+1/2, z1/2.
 

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

First citationBruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationGrossel, C. M., Dwyer, A. N., Hursthouse, M. B. & Orton, J. B. (2006). CrystEngComm, 8, 123–128.  Web of Science CrossRef CAS
First citationJin, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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