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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3029
https://doi.org/10.1107/S1600536812038196

4-(Cyclo­propane­carboxamido)­benzoic acid

Zhong-Qiang Sun,a Zhen-Ya Dinga and Zhi-Yu Shaoa*

aCollege of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China
*Correspondence e-mail: zyshao@dhu.edu.cn

(Received 9 July 2012; accepted 6 September 2012; online 29 September 2012)

In the title compound, C11H11NO3, the dihedral angle between the benzene ring and the cyclo­propane ring is 63.2 (1)°. In the crystal, mol­ecules are linked through classical cyclic carb­oxy­lic acid O—H⋯O hydrogen-bond inter­actions [graph set R22(8)] giving centrosymmetric dimers which are extended along the b-axis direction through amide N—H⋯O hydrogen-bond inter­actions, giving one-dimensional ribbon structures. Weak C—H⋯O inter­actions are also present in the structure.

Related literature

For general background to the biological activity of similar substituted benzoic acids, see: Gediya et al. (2008[Gediya, L. K., Belosay, A., Khandelwal, A. & Purushottamachar, P. (2008). Bioorg. Med. Chem. 16, 3352-3360.]). For applications of analogs of the title compound, see: Sobotka et al. (1991[Sobotka, W., Nawrot, J. & Konopinska, D. (1991). Mater. Sesji Naukowej Instytutu Ochrony Roslin, 30, 11-14.]); Chernoivanov et al. (1993[Chernoivanov, V. A. (1993). Zh. Org. Khim. II, 29, 2148-2152.], 1997[Chernoivanov, V. A. (1997). Mol. Cryst. Liq. Cryst. A, 297, 239-245.]). For graph-set analysis, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data

  • C11H11NO3

  • Mr = 205.21

  • Monoclinic, P 21 /n

  • a = 13.2429 (14) Å

  • b = 4.7704 (5) Å

  • c = 16.7983 (18) Å

  • β = 111.227 (2)°

  • V = 989.21 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.31 × 0.21 × 0.17 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.789, Tmax = 1.000

  • 5558 measured reflections

  • 1934 independent reflections

  • 1682 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.119

  • S = 1.05

  • 1934 reflections

  • 145 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.827 (18) 2.144 (19) 2.9273 (16) 158.2 (16)
O3—H3⋯O2ii 0.87 (2) 1.80 (2) 2.6685 (15) 173 (3)
C2—H2⋯O1i 0.98 2.37 3.2034 (18) 142
C3—H3B⋯O2iii 0.97 2.54 3.350 (2) 141
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y, -z; (iii) -x+1, -y, -z.

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: sAINT (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038196/zs2222sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038196/zs2222Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038196/zs2222Isup3.cml

checkCIF report


Comment top

The title compound, C11H11NO3, has been of great interest for many years because it has different biological activities and been used as a ligand in the synthesis of various Cathepsin-S reversible inhibitor compounds (Gediya et al., 2008). In order to obtain a new potentially active histone deacetylase inhibitor, the title compound was synthesized and its crystal structure is reported here. In this molecule (Fig. 1), the dihedral angle between the benzene ring and the cyclopropane ring is 63.2 (1)°. In the crystal, molecules are linked through classic cyclic carboxylic acid O—H···O hydrogen-bonding interactions [graph set R22(8) (Etter et al., 1990)] giving centrosymmetric dimers which are extended along b through amide N—H···O hydrogen-bonding interactions (Table 1), giving one-dimensional ribbon structures (Fig. 2). Present also in the structure are weak C—H···O interactions to both amide and carboxyl O-acceptors.

Related literature top

For general background to the biological activity of similar substituted benzoic acids, see: Gediya et al. (2008). For applications of analogs of the title compound, see: Sobotka et al. (1991); Chernoivanov et al. (1993, 1997). For graph-set analysis, see: Etter et al. (1990).

Experimental top

Cyclopropanecarboxylic acid (500mg, 5.8 mmol) and N, N'- carbonyldiimidazole (1.035 g, 6.38 mmol) were dissolved in acetonitrile (5ml) and the solotion was stirred for 0.5h, then added dropwise into 5 ml of an acetonitrile solution of 4-aminobenzoic acid (1.59 g, 11.6 mmol). This solution was then added dropwise to 5 ml of a trifluoroacetic acid solution in acetonitrile (727 mg, 6.38 mmol) which was stirred for 1h. The resulting mixture was dried, then diluted with ethyl acetate, washed with water, then dried in vacuo. The residue was purified by colunm chromatography (CH3OH/CH2Cl2, 5/95). Crystals suitable for X-ray diffraction were grown in a dilute CH3OH/CH2Cl2 solution at room temperature by slow evaporation.

Refinement top

Hydrogen atoms on O and N were located in a difference-Fourier map and both coordinates and isotropic displacement parameters were refined. Other H-atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C—H = 0.93 Å (aromatic) or 0.97 or 0.98 Å (aliphatic) and Uiso(H) = 1.2Ueq(C).

Structure description top

The title compound, C11H11NO3, has been of great interest for many years because it has different biological activities and been used as a ligand in the synthesis of various Cathepsin-S reversible inhibitor compounds (Gediya et al., 2008). In order to obtain a new potentially active histone deacetylase inhibitor, the title compound was synthesized and its crystal structure is reported here. In this molecule (Fig. 1), the dihedral angle between the benzene ring and the cyclopropane ring is 63.2 (1)°. In the crystal, molecules are linked through classic cyclic carboxylic acid O—H···O hydrogen-bonding interactions [graph set R22(8) (Etter et al., 1990)] giving centrosymmetric dimers which are extended along b through amide N—H···O hydrogen-bonding interactions (Table 1), giving one-dimensional ribbon structures (Fig. 2). Present also in the structure are weak C—H···O interactions to both amide and carboxyl O-acceptors.

For general background to the biological activity of similar substituted benzoic acids, see: Gediya et al. (2008). For applications of analogs of the title compound, see: Sobotka et al. (1991); Chernoivanov et al. (1993, 1997). For graph-set analysis, see: Etter et al. (1990).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: sAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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
[Figure 1] Fig. 1. A view of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. The structure of the infinite one-dimensional ribbon structures, with hydrogen bonds shown as dashed lines.
4-(Cyclopropanecarboxamido)benzoic acid top
Crystal data top
C11H11NO3F(000) = 432
Mr = 205.21Dx = 1.378 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2486 reflections
a = 13.2429 (14) Åθ = 4.9–56.1°
b = 4.7704 (5) ŵ = 0.10 mm−1
c = 16.7983 (18) ÅT = 293 K
β = 111.227 (2)°Prismatic, colorless
V = 989.21 (18) Å30.31 × 0.21 × 0.17 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		1934 independent reflections
Radiation source: fine-focus sealed tube1682 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		h = −16→16
Tmin = 0.789, Tmax = 1.000k = −5→5
5558 measured reflectionsl = −20→15
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)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0639P)2 + 0.2147P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1934 reflectionsΔρmax = 0.15 e Å−3
145 parametersΔρmin = −0.20 e Å−3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (4)
Crystal data top
C11H11NO3V = 989.21 (18) Å3
Mr = 205.21Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.2429 (14) ŵ = 0.10 mm−1
b = 4.7704 (5) ÅT = 293 K
c = 16.7983 (18) Å0.31 × 0.21 × 0.17 mm
β = 111.227 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		1934 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		1682 reflections with I > 2σ(I)
Tmin = 0.789, Tmax = 1.000Rint = 0.022
5558 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.15 e Å−3
1934 reflectionsΔρmin = −0.20 e Å−3
145 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N10.56625 (9)0.5748 (2)0.15289 (8)0.0404 (3)
O10.49517 (9)0.1514 (2)0.16147 (9)0.0605 (4)
O20.87070 (9)−0.0148 (3)−0.01839 (8)0.0707 (4)
O30.98671 (9)0.2842 (3)0.06937 (8)0.0647 (4)
C10.49424 (11)0.4057 (3)0.16928 (9)0.0394 (3)
C20.41426 (12)0.5484 (3)0.19760 (11)0.0498 (4)
H20.42170.75200.20530.060*
C30.30111 (13)0.4331 (4)0.16602 (12)0.0649 (5)
H3A0.24180.56560.15330.078*
H3B0.28620.27070.12880.078*
C40.36945 (14)0.3933 (4)0.25499 (11)0.0591 (5)
H4A0.39690.20610.27300.071*
H4B0.35240.50100.29750.071*
C50.64690 (10)0.4785 (3)0.12217 (8)0.0361 (3)
C60.75069 (11)0.5867 (3)0.15619 (10)0.0466 (4)
H60.76710.72350.19840.056*
C70.83018 (11)0.4915 (3)0.12747 (9)0.0479 (4)
H70.89980.56490.15050.058*
C80.80668 (10)0.2874 (3)0.06466 (9)0.0407 (3)
C90.70189 (11)0.1846 (3)0.02946 (9)0.0471 (4)
H90.68500.0505−0.01360.057*
C100.62238 (11)0.2803 (3)0.05789 (9)0.0449 (4)
H100.55220.21110.03370.054*
C110.89105 (11)0.1726 (3)0.03496 (9)0.0447 (4)
H10.5640 (13)0.744 (4)0.1630 (10)0.049 (5)*
H31.0297 (19)0.200 (5)0.0483 (16)0.110 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0449 (6)0.0271 (6)0.0596 (7)0.0002 (5)0.0314 (6)−0.0046 (5)
O10.0739 (8)0.0284 (5)0.1042 (9)0.0011 (5)0.0621 (7)−0.0012 (5)
O20.0470 (6)0.0924 (10)0.0813 (8)−0.0001 (6)0.0334 (6)−0.0349 (7)
O30.0408 (6)0.0872 (9)0.0737 (8)−0.0002 (6)0.0300 (6)−0.0204 (7)
C10.0437 (7)0.0293 (7)0.0531 (8)0.0010 (5)0.0270 (6)−0.0004 (5)
C20.0569 (9)0.0321 (7)0.0781 (11)−0.0027 (6)0.0457 (8)−0.0058 (7)
C30.0451 (8)0.0789 (12)0.0805 (12)0.0013 (8)0.0345 (8)−0.0126 (10)
C40.0635 (10)0.0607 (10)0.0722 (11)−0.0040 (8)0.0474 (9)−0.0034 (8)
C50.0384 (7)0.0319 (6)0.0445 (7)0.0036 (5)0.0226 (6)0.0031 (5)
C60.0456 (8)0.0478 (8)0.0527 (8)−0.0067 (6)0.0252 (6)−0.0136 (6)
C70.0357 (7)0.0583 (9)0.0534 (8)−0.0053 (6)0.0204 (6)−0.0091 (7)
C80.0385 (7)0.0473 (8)0.0413 (7)0.0064 (6)0.0206 (6)0.0030 (6)
C90.0435 (7)0.0532 (9)0.0499 (8)−0.0001 (6)0.0231 (6)−0.0135 (7)
C100.0349 (7)0.0503 (8)0.0524 (8)−0.0026 (6)0.0193 (6)−0.0098 (6)
C110.0391 (7)0.0559 (9)0.0434 (7)0.0063 (6)0.0199 (6)0.0008 (7)
Geometric parameters (Å, º) top
N1—C11.3515 (17)C4—H4A0.9700
N1—C51.4202 (16)C4—H4B0.9700
N1—H10.827 (18)C5—C101.3827 (19)
O1—C11.2208 (17)C5—C61.3832 (19)
O2—C111.2249 (19)C6—C71.3839 (19)
O3—C111.3007 (18)C6—H60.9300
O3—H30.870 (17)C7—C81.386 (2)
C1—C21.4753 (18)C7—H70.9300
C2—C41.498 (2)C8—C91.386 (2)
C2—C31.501 (2)C8—C111.4834 (18)
C2—H20.9800C9—C101.3817 (19)
C3—C41.452 (3)C9—H90.9300
C3—H3A0.9700C10—H100.9300
C3—H3B0.9700
C1—N1—C5124.04 (11)C2—C4—H4B117.7
C1—N1—H1117.4 (11)H4A—C4—H4B114.8
C5—N1—H1118.6 (11)C10—C5—C6119.67 (12)
C11—O3—H3107.8 (18)C10—C5—N1120.68 (12)
O1—C1—N1122.42 (12)C6—C5—N1119.65 (12)
O1—C1—C2121.98 (12)C5—C6—C7120.07 (13)
N1—C1—C2115.59 (12)C5—C6—H6120.0
C1—C2—C4118.53 (13)C7—C6—H6120.0
C1—C2—C3117.27 (13)C6—C7—C8120.44 (13)
C4—C2—C357.93 (11)C6—C7—H7119.8
C1—C2—H2116.7C8—C7—H7119.8
C4—C2—H2116.7C7—C8—C9119.16 (12)
C3—C2—H2116.7C7—C8—C11121.77 (13)
C4—C3—C260.91 (11)C9—C8—C11119.06 (13)
C4—C3—H3A117.7C10—C9—C8120.42 (13)
C2—C3—H3A117.7C10—C9—H9119.8
C4—C3—H3B117.7C8—C9—H9119.8
C2—C3—H3B117.7C9—C10—C5120.19 (13)
H3A—C3—H3B114.8C9—C10—H10119.9
C3—C4—C261.15 (11)C5—C10—H10119.9
C3—C4—H4A117.7O2—C11—O3123.00 (13)
C2—C4—H4A117.7O2—C11—C8121.50 (13)
C3—C4—H4B117.7O3—C11—C8115.50 (13)
C5—N1—C1—O12.5 (2)C5—C6—C7—C8−0.1 (2)
C5—N1—C1—C2−177.69 (12)C6—C7—C8—C91.6 (2)
O1—C1—C2—C428.8 (2)C6—C7—C8—C11−177.50 (14)
N1—C1—C2—C4−150.99 (15)C7—C8—C9—C10−1.3 (2)
O1—C1—C2—C3−37.6 (2)C11—C8—C9—C10177.75 (13)
N1—C1—C2—C3142.56 (15)C8—C9—C10—C5−0.4 (2)
C1—C2—C3—C4108.12 (16)C6—C5—C10—C91.9 (2)
C1—C2—C4—C3−105.96 (17)N1—C5—C10—C9−178.93 (14)
C1—N1—C5—C1043.3 (2)C7—C8—C11—O2177.35 (16)
C1—N1—C5—C6−137.46 (15)C9—C8—C11—O2−1.7 (2)
C10—C5—C6—C7−1.6 (2)C7—C8—C11—O3−2.6 (2)
N1—C5—C6—C7179.14 (13)C9—C8—C11—O3178.37 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.827 (18)2.144 (19)2.9273 (16)158.2 (16)
O3—H3···O2ii0.87 (2)1.80 (2)2.6685 (15)173 (3)
C2—H2···O1i0.982.373.2034 (18)142
C3—H3B···O2iii0.972.543.350 (2)141
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y, −z; (iii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formulaC11H11NO3
Mr205.21
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)13.2429 (14), 4.7704 (5), 16.7983 (18)
β (°) 111.227 (2)
V (Å3)989.21 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.31 × 0.21 × 0.17
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.789, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		5558, 1934, 1682
Rint0.022
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.119, 1.05
No. of reflections1934
No. of parameters145
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.20

Computer programs: SMART (Bruker, 2003), sAINT (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.827 (18)2.144 (19)2.9273 (16)158.2 (16)
O3—H3···O2ii0.870 (17)1.803 (17)2.6685 (15)173 (3)
C2—H2···O1i0.982.373.2034 (18)142
C3—H3B···O2iii0.972.543.350 (2)141
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y, −z; (iii) −x+1, −y, −z.
 

Acknowledgements

This work was supported by the Fundamental Research Funds for the Central Universities.

References

First citationBruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChernoivanov, V. A. (1993). Zh. Org. Khim. II, 29, 2148-2152.  Google Scholar
 First citationChernoivanov, V. A. (1997). Mol. Cryst. Liq. Cryst. A, 297, 239-245.  CrossRef CAS Google Scholar
 First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationGediya, L. K., Belosay, A., Khandelwal, A. & Purushottamachar, P. (2008). Bioorg. Med. Chem. 16, 3352–3360.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSobotka, W., Nawrot, J. & Konopinska, D. (1991). Mater. Sesji Naukowej Instytutu Ochrony Roslin, 30, 11–14.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3029
https://doi.org/10.1107/S1600536812038196
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