N-(4-Chloro-phen-yl)succinamic acid.

In the title compound, C(10)H(10)ClNO(3), the conformation of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and further, they are anti to the H atoms of their adjacent -CH(2) groups. The C=O and O-H bonds of the acid group are in the syn position relative to each other. In the crystal, mol-ecules are packed into infinite chains through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For our study of the effect of ring and side-chain substitution on the solid-state geometry of anilides, see: Gowda et al. (2009 ▶). For the modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). The packing of mol­ecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C10H10ClNO3

M = 227.64

Monoclinic,

a = 15.908 (1) Å

b = 4.8778 (4) Å

c = 14.286 (1) Å

β = 109.787 (6)°

V = 1043.09 (13) Å3

Z = 4

Cu Kα radiation

μ = 3.16 mm−1

T = 299 K

0.55 × 0.43 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.265, T max = 0.623

3006 measured reflections

1837 independent reflections

1643 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.121

S = 1.04

1837 reflections

143 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902649X/bv2121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902649X/bv2121Isup2.hkl

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

C10H10ClNO3	F(000) = 472
Mr = 227.64	Dx = 1.450 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 15.908 (1) Å	θ = 6.6–18.1°
b = 4.8778 (4) Å	µ = 3.16 mm−1
c = 14.286 (1) Å	T = 299 K
β = 109.787 (6)°	Prism, colourless
V = 1043.09 (13) Å3	0.55 × 0.43 × 0.15 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1643 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 67.0°, θmin = 3.0°
ω/2θ scans	h = −18→18
Absorption correction: ψ scan (North et al., 1968)	k = 0→5
Tmin = 0.265, Tmax = 0.623	l = −17→8
3006 measured reflections	3 standard reflections every 120 min
1837 independent reflections	intensity decay: 1.0%

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.4605P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.004
1837 reflections	Δρmax = 0.30 e Å−3
143 parameters	Δρmin = −0.26 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: 0.0090 (10)

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
C1	0.71205 (12)	0.4065 (4)	0.91702 (13)	0.0401 (4)
C2	0.72512 (14)	0.5563 (4)	0.84114 (15)	0.0508 (5)
H2	0.7675	0.6958	0.8560	0.061*
C3	0.67546 (16)	0.4998 (5)	0.74299 (15)	0.0572 (6)
H3	0.6834	0.6028	0.6919	0.069*
C4	0.61449 (13)	0.2907 (5)	0.72194 (14)	0.0498 (5)
C5	0.60089 (14)	0.1398 (5)	0.79657 (15)	0.0524 (5)
H5	0.5591	−0.0013	0.7813	0.063*
C6	0.64971 (14)	0.1987 (4)	0.89477 (15)	0.0478 (5)
H6	0.6404	0.0981	0.9457	0.057*
C7	0.79738 (13)	0.3002 (4)	1.09135 (13)	0.0410 (4)
C8	0.83960 (13)	0.4299 (4)	1.19225 (13)	0.0439 (5)
H8A	0.8661	0.6037	1.1844	0.053*
H8B	0.7936	0.4669	1.2210	0.053*
C9	0.91033 (14)	0.2509 (4)	1.26240 (14)	0.0453 (5)
H9A	0.8848	0.0720	1.2655	0.054*
H9B	0.9584	0.2261	1.2358	0.054*
C10	0.94834 (12)	0.3632 (4)	1.36527 (14)	0.0422 (4)
N1	0.76140 (12)	0.4779 (3)	1.01677 (11)	0.0448 (4)
H1N	0.7718 (15)	0.641 (4)	1.0297 (17)	0.054*
O1	0.79464 (12)	0.0511 (3)	1.08006 (11)	0.0594 (5)
O2	1.01272 (13)	0.2126 (4)	1.42350 (12)	0.0704 (6)
H2O	1.032 (2)	0.281 (6)	1.481 (2)	0.084*
O3	0.92375 (12)	0.5735 (4)	1.39202 (10)	0.0695 (5)
Cl1	0.55277 (5)	0.21449 (18)	0.59903 (4)	0.0831 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0446 (9)	0.0350 (10)	0.0343 (9)	0.0029 (8)	0.0052 (7)	−0.0037 (7)
C2	0.0572 (12)	0.0453 (12)	0.0449 (11)	−0.0117 (10)	0.0109 (9)	−0.0018 (9)
C3	0.0683 (13)	0.0631 (14)	0.0383 (10)	−0.0065 (11)	0.0158 (9)	0.0009 (10)
C4	0.0457 (10)	0.0640 (14)	0.0353 (10)	0.0035 (10)	0.0081 (8)	−0.0096 (9)
C5	0.0463 (10)	0.0561 (13)	0.0480 (11)	−0.0113 (10)	0.0071 (9)	−0.0092 (10)
C6	0.0508 (11)	0.0496 (12)	0.0382 (10)	−0.0095 (9)	0.0089 (8)	−0.0018 (8)
C7	0.0493 (10)	0.0305 (10)	0.0361 (9)	−0.0018 (8)	0.0053 (8)	−0.0045 (7)
C8	0.0554 (11)	0.0318 (10)	0.0348 (9)	0.0005 (8)	0.0024 (8)	−0.0044 (7)
C9	0.0522 (11)	0.0385 (10)	0.0370 (10)	0.0028 (8)	0.0045 (8)	−0.0046 (8)
C10	0.0461 (10)	0.0382 (10)	0.0367 (9)	0.0020 (8)	0.0068 (8)	0.0002 (8)
N1	0.0583 (10)	0.0279 (8)	0.0369 (8)	−0.0039 (7)	0.0011 (7)	−0.0042 (6)
O1	0.0879 (11)	0.0271 (8)	0.0449 (8)	−0.0005 (7)	−0.0014 (7)	−0.0053 (6)
O2	0.0840 (12)	0.0641 (11)	0.0407 (8)	0.0300 (9)	−0.0082 (8)	−0.0093 (7)
O3	0.0830 (11)	0.0628 (11)	0.0412 (8)	0.0300 (9)	−0.0070 (7)	−0.0147 (7)
Cl1	0.0851 (5)	0.1153 (7)	0.0360 (3)	−0.0133 (4)	0.0037 (3)	−0.0179 (3)

C1—C6	1.378 (3)	C7—N1	1.342 (2)
C1—C2	1.380 (3)	C7—C8	1.508 (2)
C1—N1	1.418 (2)	C8—C9	1.506 (3)
C2—C3	1.384 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.369 (3)	C9—C10	1.491 (3)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.372 (3)	C9—H9B	0.9700
C4—Cl1	1.7373 (19)	C10—O3	1.205 (2)
C5—C6	1.384 (3)	C10—O2	1.305 (2)
C5—H5	0.9300	N1—H1N	0.819 (17)
C6—H6	0.9300	O2—H2O	0.85 (3)
C7—O1	1.225 (2)
C6—C1—C2	119.75 (18)	N1—C7—C8	114.84 (15)
C6—C1—N1	121.52 (18)	C9—C8—C7	112.54 (16)
C2—C1—N1	118.68 (18)	C9—C8—H8A	109.1
C1—C2—C3	120.3 (2)	C7—C8—H8A	109.1
C1—C2—H2	119.9	C9—C8—H8B	109.1
C3—C2—H2	119.9	C7—C8—H8B	109.1
C4—C3—C2	119.3 (2)	H8A—C8—H8B	107.8
C4—C3—H3	120.3	C10—C9—C8	113.89 (16)
C2—C3—H3	120.3	C10—C9—H9A	108.8
C3—C4—C5	121.03 (19)	C8—C9—H9A	108.8
C3—C4—Cl1	119.83 (17)	C10—C9—H9B	108.8
C5—C4—Cl1	119.14 (17)	C8—C9—H9B	108.8
C4—C5—C6	119.6 (2)	H9A—C9—H9B	107.7
C4—C5—H5	120.2	O3—C10—O2	123.09 (18)
C6—C5—H5	120.2	O3—C10—C9	123.94 (17)
C1—C6—C5	119.98 (19)	O2—C10—C9	112.96 (17)
C1—C6—H6	120.0	C7—N1—C1	125.55 (16)
C5—C6—H6	120.0	C7—N1—H1N	116.6 (17)
O1—C7—N1	123.35 (17)	C1—N1—H1N	117.8 (17)
O1—C7—C8	121.79 (17)	C10—O2—H2O	110 (2)
C6—C1—C2—C3	0.4 (3)	O1—C7—C8—C9	26.2 (3)
N1—C1—C2—C3	−177.3 (2)	N1—C7—C8—C9	−155.58 (18)
C1—C2—C3—C4	−1.2 (4)	C7—C8—C9—C10	−175.40 (17)
C2—C3—C4—C5	1.1 (4)	C8—C9—C10—O3	2.1 (3)
C2—C3—C4—Cl1	−179.15 (18)	C8—C9—C10—O2	−176.62 (19)
C3—C4—C5—C6	−0.2 (3)	O1—C7—N1—C1	3.3 (3)
Cl1—C4—C5—C6	180.00 (17)	C8—C7—N1—C1	−174.84 (18)
C2—C1—C6—C5	0.4 (3)	C6—C1—N1—C7	42.0 (3)
N1—C1—C6—C5	178.14 (19)	C2—C1—N1—C7	−140.3 (2)
C4—C5—C6—C1	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (2)	2.12 (2)	2.931 (2)	173 (2)
O2—H2O···O3ii	0.85 (3)	1.85 (3)	2.693 (2)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.819 (17)	2.117 (17)	2.931 (2)	173 (2)
O2—H2O⋯O3ii	0.85 (3)	1.85 (3)	2.693 (2)	179 (3)

Symmetry codes: (i) ; (ii) .