2-(4-Chloro-benzamido)-acetic acid.

In the crystal structure of the title mol-ecule, C(9)H(8)ClNO(3), adjacent mol-ecules are arranged into centrosymmetric dimers through pairs of inter-molecular O-H⋯O inter-actions. Inter-molecular N-H⋯O hydrogen bonds link the dimers into a layer parallel to the bc plane. In the layer, mol-ecules are packed in a face-to-face π-stacked arrangment, showing π-π stacking inter-actions between the benzene rings with a centroid-centroid distance of 3.6884 (8) Å.

Related literature

For crystallographic studies of benzamide derivatives, see: Donnelly et al. (2008 ▶); Mugnoli et al. (1991 ▶); Stensland et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H8ClNO3

M = 213.61

Monoclinic,

a = 10.5035 (2) Å

b = 13.2105 (4) Å

c = 7.1226 (2) Å

β = 102.203 (1)°

V = 965.98 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.36 × 0.21 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

9027 measured reflections

2365 independent reflections

1627 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.02

2365 reflections

133 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009536/is2688sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009536/is2688Isup2.hkl

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

C9H8ClNO3	F(000) = 440
Mr = 213.61	Dx = 1.469 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3071 reflections
a = 10.5035 (2) Å	θ = 2.5–26.5°
b = 13.2105 (4) Å	µ = 0.37 mm−1
c = 7.1226 (2) Å	T = 296 K
β = 102.203 (1)°	Needle, colourless
V = 965.98 (4) Å3	0.36 × 0.21 × 0.13 mm
Z = 4

Bruker APEXII CCD diffractometer	1627 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.028
graphite	θmax = 28.3°, θmin = 3.3°
φ and ω scans	h = −13→13
9027 measured reflections	k = −17→17
2365 independent reflections	l = −9→9

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.1658P] where P = (Fo2 + 2Fc2)/3
2365 reflections	(Δ/σ)max = 0.001
133 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	1.15861 (4)	0.81838 (4)	0.19567 (7)	0.0678 (2)
O1	0.65691 (11)	0.52525 (8)	0.26411 (16)	0.0518 (4)
O2	0.46720 (11)	0.64368 (9)	0.49155 (17)	0.0576 (4)
O3	0.31367 (11)	0.53263 (9)	0.37136 (17)	0.0519 (4)
N1	0.53959 (13)	0.65903 (11)	0.1375 (2)	0.0515 (5)
C1	0.88594 (15)	0.60968 (12)	0.1921 (2)	0.0457 (5)
C2	1.00353 (16)	0.65563 (13)	0.1908 (2)	0.0499 (6)
C3	1.00957 (15)	0.75964 (13)	0.1880 (2)	0.0453 (5)
C4	0.90087 (16)	0.81827 (12)	0.1838 (2)	0.0465 (5)
C5	0.78344 (15)	0.77170 (11)	0.1832 (2)	0.0423 (5)
C6	0.77497 (14)	0.66710 (11)	0.1887 (2)	0.0379 (4)
C7	0.65311 (14)	0.61215 (11)	0.2002 (2)	0.0407 (5)
C8	0.41924 (16)	0.61044 (15)	0.1527 (2)	0.0539 (6)
C9	0.40478 (14)	0.59869 (11)	0.3568 (2)	0.0411 (5)
H1	0.88100	0.53940	0.19530	0.0550*
H1N	0.538 (2)	0.7167 (13)	0.092 (3)	0.0810*
H1O	0.315 (2)	0.5241 (19)	0.487 (2)	0.1020*
H2	1.07760	0.61690	0.19170	0.0600*
H4	0.90650	0.88850	0.18130	0.0560*
H5	0.70930	0.81080	0.17910	0.0510*
H8A	0.41540	0.54410	0.09330	0.0650*
H8B	0.34680	0.65000	0.08250	0.0650*

	U11	U22	U33	U12	U13	U23
Cl1	0.0478 (3)	0.0785 (4)	0.0752 (3)	−0.0209 (2)	0.0086 (2)	−0.0017 (2)
O1	0.0541 (7)	0.0422 (7)	0.0616 (7)	0.0003 (5)	0.0180 (5)	0.0100 (5)
O2	0.0571 (8)	0.0578 (7)	0.0566 (7)	−0.0178 (6)	0.0089 (6)	−0.0106 (6)
O3	0.0439 (6)	0.0499 (7)	0.0600 (7)	−0.0122 (5)	0.0067 (5)	0.0017 (6)
N1	0.0389 (8)	0.0556 (9)	0.0604 (9)	0.0027 (6)	0.0113 (6)	0.0169 (7)
C1	0.0449 (9)	0.0391 (8)	0.0547 (9)	0.0039 (7)	0.0141 (7)	0.0045 (7)
C2	0.0392 (9)	0.0546 (10)	0.0566 (10)	0.0065 (7)	0.0119 (7)	0.0016 (7)
C3	0.0414 (9)	0.0532 (10)	0.0401 (8)	−0.0082 (7)	0.0060 (6)	−0.0003 (7)
C4	0.0524 (10)	0.0391 (8)	0.0461 (9)	−0.0040 (7)	0.0061 (7)	0.0011 (7)
C5	0.0431 (9)	0.0409 (8)	0.0425 (8)	0.0065 (6)	0.0081 (6)	0.0036 (6)
C6	0.0395 (8)	0.0407 (8)	0.0338 (7)	0.0019 (6)	0.0084 (6)	0.0048 (6)
C7	0.0435 (9)	0.0406 (9)	0.0394 (8)	0.0018 (6)	0.0117 (6)	0.0035 (6)
C8	0.0374 (9)	0.0698 (12)	0.0530 (10)	−0.0044 (8)	0.0065 (7)	−0.0001 (8)
C9	0.0300 (8)	0.0351 (8)	0.0568 (9)	0.0026 (6)	0.0062 (7)	−0.0004 (7)

Cl1—C3	1.7377 (17)	C3—C4	1.375 (2)
O1—C7	1.2325 (18)	C4—C5	1.378 (2)
O2—C9	1.1993 (19)	C5—C6	1.386 (2)
O3—C9	1.3153 (19)	C6—C7	1.489 (2)
O3—H1O	0.829 (14)	C8—C9	1.501 (2)
N1—C8	1.442 (2)	C1—H1	0.9300
N1—C7	1.334 (2)	C2—H2	0.9300
N1—H1N	0.827 (18)	C4—H4	0.9300
C1—C2	1.378 (2)	C5—H5	0.9300
C1—C6	1.387 (2)	C8—H8A	0.9700
C2—C3	1.376 (2)	C8—H8B	0.9700
C9—O3—H1O	108.0 (16)	N1—C8—C9	112.86 (13)
C7—N1—C8	120.26 (14)	O2—C9—O3	123.33 (14)
C7—N1—H1N	120.1 (15)	O2—C9—C8	125.00 (14)
C8—N1—H1N	119.6 (15)	O3—C9—C8	111.66 (13)
C2—C1—C6	120.68 (15)	C2—C1—H1	120.00
C1—C2—C3	118.96 (15)	C6—C1—H1	120.00
C2—C3—C4	121.49 (15)	C1—C2—H2	120.00
Cl1—C3—C2	119.31 (13)	C3—C2—H2	121.00
Cl1—C3—C4	119.18 (13)	C3—C4—H4	120.00
C3—C4—C5	119.17 (15)	C5—C4—H4	120.00
C4—C5—C6	120.53 (14)	C4—C5—H5	120.00
C1—C6—C5	119.16 (14)	C6—C5—H5	120.00
C1—C6—C7	117.49 (13)	N1—C8—H8A	109.00
C5—C6—C7	123.29 (14)	N1—C8—H8B	109.00
N1—C7—C6	118.25 (13)	C9—C8—H8A	109.00
O1—C7—N1	120.86 (14)	C9—C8—H8B	109.00
O1—C7—C6	120.89 (13)	H8A—C8—H8B	108.00
C8—N1—C7—C6	−177.54 (13)	C3—C4—C5—C6	0.6 (2)
C7—N1—C8—C9	67.7 (2)	C4—C5—C6—C7	176.22 (13)
C8—N1—C7—O1	3.2 (2)	C4—C5—C6—C1	−0.9 (2)
C2—C1—C6—C7	−177.03 (13)	C1—C6—C7—O1	20.2 (2)
C2—C1—C6—C5	0.3 (2)	C1—C6—C7—N1	−159.08 (14)
C6—C1—C2—C3	0.6 (2)	C5—C6—C7—O1	−156.98 (14)
C1—C2—C3—Cl1	177.54 (11)	C5—C6—C7—N1	23.8 (2)
C1—C2—C3—C4	−0.9 (2)	N1—C8—C9—O2	16.7 (2)
Cl1—C3—C4—C5	−178.18 (11)	N1—C8—C9—O3	−163.65 (14)
C2—C3—C4—C5	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.06 (2)	2.8491 (19)	160 (2)
O3—H1O···O1ii	0.83 (1)	1.85 (2)	2.6613 (16)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.06 (2)	2.8491 (19)	160 (2)
O3—H1O⋯O1ii	0.83 (1)	1.85 (2)	2.6613 (16)	165 (2)

Symmetry codes: (i) ; (ii) .