4-(Cyclo-propane-carboxamido)-benzoic acid.

In the title compound, C(11)H(11)NO(3), the dihedral angle between the benzene ring and the cyclo-propane ring is 63.2 (1)°. In the crystal, mol-ecules are linked through classical cyclic carb-oxy-lic acid O-H⋯O hydrogen-bond inter-actions [graph set R(2) (2)(8)] giving centrosymmetric dimers which are extended along the b-axis direction through amide N-H⋯O hydrogen-bond inter-actions, giving one-dimensional ribbon structures. Weak C-H⋯O inter-actions 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 ▶). 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

Crystal data

C11H11NO3

M = 205.21

Monoclinic,

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 ▶) T min = 0.789, T max = 1.000

5558 measured reflections

1934 independent reflections

1682 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 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

Data collection: SMART (Bruker, 2003 ▶); cell refinement: sAINT (Bruker, 2003 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038196/zs2222sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038196/zs2222Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038196/zs2222Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H11NO3	F(000) = 432
Mr = 205.21	Dx = 1.378 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2486 reflections
a = 13.2429 (14) Å	θ = 4.9–56.1°
b = 4.7704 (5) Å	µ = 0.10 mm−1
c = 16.7983 (18) Å	T = 293 K
β = 111.227 (2)°	Prismatic, colorless
V = 989.21 (18) Å3	0.31 × 0.21 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1934 independent reflections
Radiation source: fine-focus sealed tube	1682 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −16→16
Tmin = 0.789, Tmax = 1.000	k = −5→5
5558 measured reflections	l = −20→15

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)] = 0.041	H 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 reflections	Δρmax = 0.15 e Å−3
145 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (4)

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.

	x	y	z	Uiso*/Ueq
N1	0.56625 (9)	0.5748 (2)	0.15289 (8)	0.0404 (3)
O1	0.49517 (9)	0.1514 (2)	0.16147 (9)	0.0605 (4)
O2	0.87070 (9)	−0.0148 (3)	−0.01839 (8)	0.0707 (4)
O3	0.98671 (9)	0.2842 (3)	0.06937 (8)	0.0647 (4)
C1	0.49424 (11)	0.4057 (3)	0.16928 (9)	0.0394 (3)
C2	0.41426 (12)	0.5484 (3)	0.19760 (11)	0.0498 (4)
H2	0.4217	0.7520	0.2053	0.060*
C3	0.30111 (13)	0.4331 (4)	0.16602 (12)	0.0649 (5)
H3A	0.2418	0.5656	0.1533	0.078*
H3B	0.2862	0.2707	0.1288	0.078*
C4	0.36945 (14)	0.3933 (4)	0.25499 (11)	0.0591 (5)
H4A	0.3969	0.2061	0.2730	0.071*
H4B	0.3524	0.5010	0.2975	0.071*
C5	0.64690 (10)	0.4785 (3)	0.12217 (8)	0.0361 (3)
C6	0.75069 (11)	0.5867 (3)	0.15619 (10)	0.0466 (4)
H6	0.7671	0.7235	0.1984	0.056*
C7	0.83018 (11)	0.4915 (3)	0.12747 (9)	0.0479 (4)
H7	0.8998	0.5649	0.1505	0.058*
C8	0.80668 (10)	0.2874 (3)	0.06466 (9)	0.0407 (3)
C9	0.70189 (11)	0.1846 (3)	0.02946 (9)	0.0471 (4)
H9	0.6850	0.0505	−0.0136	0.057*
C10	0.62238 (11)	0.2803 (3)	0.05789 (9)	0.0449 (4)
H10	0.5522	0.2111	0.0337	0.054*
C11	0.89105 (11)	0.1726 (3)	0.03496 (9)	0.0447 (4)
H1	0.5640 (13)	0.744 (4)	0.1630 (10)	0.049 (5)*
H3	1.0297 (19)	0.200 (5)	0.0483 (16)	0.110 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0449 (6)	0.0271 (6)	0.0596 (7)	0.0002 (5)	0.0314 (6)	−0.0046 (5)
O1	0.0739 (8)	0.0284 (5)	0.1042 (9)	0.0011 (5)	0.0621 (7)	−0.0012 (5)
O2	0.0470 (6)	0.0924 (10)	0.0813 (8)	−0.0001 (6)	0.0334 (6)	−0.0349 (7)
O3	0.0408 (6)	0.0872 (9)	0.0737 (8)	−0.0002 (6)	0.0300 (6)	−0.0204 (7)
C1	0.0437 (7)	0.0293 (7)	0.0531 (8)	0.0010 (5)	0.0270 (6)	−0.0004 (5)
C2	0.0569 (9)	0.0321 (7)	0.0781 (11)	−0.0027 (6)	0.0457 (8)	−0.0058 (7)
C3	0.0451 (8)	0.0789 (12)	0.0805 (12)	0.0013 (8)	0.0345 (8)	−0.0126 (10)
C4	0.0635 (10)	0.0607 (10)	0.0722 (11)	−0.0040 (8)	0.0474 (9)	−0.0034 (8)
C5	0.0384 (7)	0.0319 (6)	0.0445 (7)	0.0036 (5)	0.0226 (6)	0.0031 (5)
C6	0.0456 (8)	0.0478 (8)	0.0527 (8)	−0.0067 (6)	0.0252 (6)	−0.0136 (6)
C7	0.0357 (7)	0.0583 (9)	0.0534 (8)	−0.0053 (6)	0.0204 (6)	−0.0091 (7)
C8	0.0385 (7)	0.0473 (8)	0.0413 (7)	0.0064 (6)	0.0206 (6)	0.0030 (6)
C9	0.0435 (7)	0.0532 (9)	0.0499 (8)	−0.0001 (6)	0.0231 (6)	−0.0135 (7)
C10	0.0349 (7)	0.0503 (8)	0.0524 (8)	−0.0026 (6)	0.0193 (6)	−0.0098 (6)
C11	0.0391 (7)	0.0559 (9)	0.0434 (7)	0.0063 (6)	0.0199 (6)	0.0008 (7)

N1—C1	1.3515 (17)	C4—H4A	0.9700
N1—C5	1.4202 (16)	C4—H4B	0.9700
N1—H1	0.827 (18)	C5—C10	1.3827 (19)
O1—C1	1.2208 (17)	C5—C6	1.3832 (19)
O2—C11	1.2249 (19)	C6—C7	1.3839 (19)
O3—C11	1.3007 (18)	C6—H6	0.9300
O3—H3	0.870 (17)	C7—C8	1.386 (2)
C1—C2	1.4753 (18)	C7—H7	0.9300
C2—C4	1.498 (2)	C8—C9	1.386 (2)
C2—C3	1.501 (2)	C8—C11	1.4834 (18)
C2—H2	0.9800	C9—C10	1.3817 (19)
C3—C4	1.452 (3)	C9—H9	0.9300
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700
C1—N1—C5	124.04 (11)	C2—C4—H4B	117.7
C1—N1—H1	117.4 (11)	H4A—C4—H4B	114.8
C5—N1—H1	118.6 (11)	C10—C5—C6	119.67 (12)
C11—O3—H3	107.8 (18)	C10—C5—N1	120.68 (12)
O1—C1—N1	122.42 (12)	C6—C5—N1	119.65 (12)
O1—C1—C2	121.98 (12)	C5—C6—C7	120.07 (13)
N1—C1—C2	115.59 (12)	C5—C6—H6	120.0
C1—C2—C4	118.53 (13)	C7—C6—H6	120.0
C1—C2—C3	117.27 (13)	C6—C7—C8	120.44 (13)
C4—C2—C3	57.93 (11)	C6—C7—H7	119.8
C1—C2—H2	116.7	C8—C7—H7	119.8
C4—C2—H2	116.7	C7—C8—C9	119.16 (12)
C3—C2—H2	116.7	C7—C8—C11	121.77 (13)
C4—C3—C2	60.91 (11)	C9—C8—C11	119.06 (13)
C4—C3—H3A	117.7	C10—C9—C8	120.42 (13)
C2—C3—H3A	117.7	C10—C9—H9	119.8
C4—C3—H3B	117.7	C8—C9—H9	119.8
C2—C3—H3B	117.7	C9—C10—C5	120.19 (13)
H3A—C3—H3B	114.8	C9—C10—H10	119.9
C3—C4—C2	61.15 (11)	C5—C10—H10	119.9
C3—C4—H4A	117.7	O2—C11—O3	123.00 (13)
C2—C4—H4A	117.7	O2—C11—C8	121.50 (13)
C3—C4—H4B	117.7	O3—C11—C8	115.50 (13)
C5—N1—C1—O1	2.5 (2)	C5—C6—C7—C8	−0.1 (2)
C5—N1—C1—C2	−177.69 (12)	C6—C7—C8—C9	1.6 (2)
O1—C1—C2—C4	28.8 (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—C10	177.75 (13)
N1—C1—C2—C3	142.56 (15)	C8—C9—C10—C5	−0.4 (2)
C1—C2—C3—C4	108.12 (16)	C6—C5—C10—C9	1.9 (2)
C1—C2—C4—C3	−105.96 (17)	N1—C5—C10—C9	−178.93 (14)
C1—N1—C5—C10	43.3 (2)	C7—C8—C11—O2	177.35 (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—C7	179.14 (13)	C9—C8—C11—O3	178.37 (13)

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

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) ; (ii) ; (iii) .