N-(3-Chloro-phen-yl)succinamic acid.

In the title compound, C(10)H(10)ClNO(3), the N-H and C=O bonds in the amide segment are trans to each other. In the crystal structure, the mol-ecules are linked 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 substitutions on the structures of anilides and for related structures, see: Gowda et al. (2009 ▶; 2010 ▶); Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C10H10ClNO3

M = 227.64

Orthorhombic,

a = 10.0308 (8) Å

b = 11.1810 (9) Å

c = 19.036 (2) Å

V = 2135.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.34 mm−1

T = 299 K

0.24 × 0.20 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.922, T max = 0.980

8200 measured reflections

2184 independent reflections

1137 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.152

S = 1.02

2184 reflections

142 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">reduction: CrysAlis RED; 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/S1600536810008949/bt5210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008949/bt5210Isup2.hkl

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

C10H10ClNO3	F(000) = 944
Mr = 227.64	Dx = 1.416 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2016 reflections
a = 10.0308 (8) Å	θ = 2.7–27.7°
b = 11.1810 (9) Å	µ = 0.34 mm−1
c = 19.036 (2) Å	T = 299 K
V = 2135.0 (3) Å3	Plate, colourless
Z = 8	0.24 × 0.20 × 0.06 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2184 independent reflections
Radiation source: fine-focus sealed tube	1137 reflections with I > 2σ(I)
graphite	Rint = 0.045
Rotation method data acquisition using ω and φ scans.	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→12
Tmin = 0.922, Tmax = 0.980	k = −12→13
8200 measured reflections	l = −22→23

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0603P)2 + 1.1737P] where P = (Fo2 + 2Fc2)/3
2184 reflections	(Δ/σ)max = 0.012
142 parameters	Δρmax = 0.30 e Å−3
2 restraints	Δρmin = −0.39 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 > 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
Cl1	0.25030 (11)	0.71276 (10)	0.20800 (6)	0.0858 (4)
O1	−0.0249 (2)	0.23883 (19)	0.02471 (13)	0.0655 (7)
O2	0.1845 (3)	0.0367 (2)	−0.03891 (14)	0.0673 (7)
O3	0.0091 (3)	−0.0318 (2)	−0.09646 (13)	0.0651 (7)
H3O	0.033 (5)	−0.097 (2)	−0.081 (2)	0.098*
N1	0.1200 (3)	0.3941 (2)	0.03276 (15)	0.0539 (8)
H1N	0.181 (3)	0.431 (3)	0.0101 (16)	0.065*
C1	0.0900 (3)	0.4445 (3)	0.09884 (18)	0.0484 (8)
C2	0.1706 (4)	0.5390 (3)	0.12010 (18)	0.0523 (9)
H2	0.2395	0.5654	0.0913	0.063*
C3	0.1482 (4)	0.5930 (3)	0.1835 (2)	0.0574 (10)
C4	0.0471 (5)	0.5568 (4)	0.2270 (2)	0.0714 (12)
H4	0.0329	0.5943	0.2700	0.086*
C5	−0.0325 (5)	0.4644 (4)	0.2058 (2)	0.0741 (12)
H5	−0.1015	0.4393	0.2349	0.089*
C6	−0.0129 (4)	0.4072 (3)	0.1420 (2)	0.0627 (10)
H6	−0.0682	0.3446	0.1284	0.075*
C7	0.0649 (3)	0.2997 (3)	−0.00050 (19)	0.0480 (8)
C8	0.1239 (3)	0.2756 (3)	−0.07174 (17)	0.0519 (9)
H8A	0.2183	0.2590	−0.0664	0.062*
H8B	0.1151	0.3468	−0.1004	0.062*
C9	0.0587 (4)	0.1716 (3)	−0.10939 (18)	0.0566 (9)
H9A	−0.0373	0.1824	−0.1086	0.068*
H9B	0.0870	0.1716	−0.1581	0.068*
C10	0.0920 (4)	0.0530 (3)	−0.07727 (17)	0.0444 (8)

	U11	U22	U33	U12	U13	U23
Cl1	0.0739 (7)	0.0821 (8)	0.1014 (9)	0.0073 (6)	−0.0183 (7)	−0.0295 (6)
O1	0.0610 (15)	0.0445 (13)	0.091 (2)	−0.0112 (12)	0.0190 (14)	0.0046 (12)
O2	0.0650 (17)	0.0477 (14)	0.0894 (19)	0.0055 (13)	−0.0291 (16)	0.0059 (13)
O3	0.0739 (18)	0.0504 (14)	0.0712 (17)	−0.0174 (15)	−0.0159 (14)	0.0058 (13)
N1	0.0531 (18)	0.0452 (16)	0.063 (2)	−0.0146 (14)	0.0162 (15)	−0.0029 (14)
C1	0.049 (2)	0.0408 (18)	0.055 (2)	0.0040 (16)	0.0087 (18)	0.0059 (16)
C2	0.045 (2)	0.054 (2)	0.058 (2)	0.0041 (18)	0.0071 (17)	0.0025 (17)
C3	0.053 (2)	0.057 (2)	0.062 (2)	0.0130 (18)	−0.009 (2)	0.0002 (19)
C4	0.088 (3)	0.075 (3)	0.052 (3)	0.019 (3)	0.008 (2)	0.004 (2)
C5	0.083 (3)	0.074 (3)	0.066 (3)	0.007 (3)	0.032 (2)	0.018 (2)
C6	0.060 (2)	0.054 (2)	0.074 (3)	−0.0032 (19)	0.018 (2)	0.0106 (19)
C7	0.0447 (18)	0.0346 (16)	0.065 (2)	0.0046 (15)	0.0048 (19)	0.0118 (16)
C8	0.056 (2)	0.0356 (17)	0.064 (2)	0.0035 (16)	0.0013 (19)	0.0076 (16)
C9	0.065 (2)	0.0490 (19)	0.056 (2)	0.0029 (18)	−0.0134 (19)	0.0037 (17)
C10	0.047 (2)	0.0430 (19)	0.0430 (19)	0.0012 (16)	0.0024 (17)	−0.0039 (15)

Cl1—C3	1.749 (4)	C4—C5	1.366 (6)
O1—C7	1.226 (4)	C4—H4	0.9300
O2—C10	1.195 (4)	C5—C6	1.388 (5)
O3—C10	1.313 (4)	C5—H5	0.9300
O3—H3O	0.820 (19)	C6—H6	0.9300
N1—C7	1.349 (4)	C7—C8	1.504 (5)
N1—C1	1.411 (4)	C8—C9	1.515 (4)
N1—H1N	0.853 (18)	C8—H8A	0.9700
C1—C6	1.384 (5)	C8—H8B	0.9700
C1—C2	1.391 (5)	C9—C10	1.498 (4)
C2—C3	1.369 (5)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.371 (5)
C10—O3—H3O	111 (3)	C1—C6—H6	120.4
C7—N1—C1	130.1 (3)	C5—C6—H6	120.4
C7—N1—H1N	116 (2)	O1—C7—N1	123.5 (3)
C1—N1—H1N	114 (2)	O1—C7—C8	122.8 (3)
C6—C1—C2	119.4 (3)	N1—C7—C8	113.7 (3)
C6—C1—N1	124.6 (3)	C7—C8—C9	113.2 (3)
C2—C1—N1	116.0 (3)	C7—C8—H8A	108.9
C3—C2—C1	119.8 (3)	C9—C8—H8A	108.9
C3—C2—H2	120.1	C7—C8—H8B	108.9
C1—C2—H2	120.1	C9—C8—H8B	108.9
C2—C3—C4	121.6 (4)	H8A—C8—H8B	107.7
C2—C3—Cl1	118.5 (3)	C10—C9—C8	112.9 (3)
C4—C3—Cl1	119.9 (3)	C10—C9—H9A	109.0
C5—C4—C3	118.5 (4)	C8—C9—H9A	109.0
C5—C4—H4	120.7	C10—C9—H9B	109.0
C3—C4—H4	120.7	C8—C9—H9B	109.0
C4—C5—C6	121.7 (4)	H9A—C9—H9B	107.8
C4—C5—H5	119.2	O2—C10—O3	123.5 (3)
C6—C5—H5	119.2	O2—C10—C9	123.9 (3)
C1—C6—C5	119.1 (4)	O3—C10—C9	112.6 (3)
C7—N1—C1—C6	−4.0 (6)	N1—C1—C6—C5	−179.8 (3)
C7—N1—C1—C2	176.7 (3)	C4—C5—C6—C1	0.2 (6)
C6—C1—C2—C3	0.6 (5)	C1—N1—C7—O1	−1.2 (5)
N1—C1—C2—C3	179.9 (3)	C1—N1—C7—C8	178.9 (3)
C1—C2—C3—C4	−0.4 (5)	O1—C7—C8—C9	1.7 (4)
C1—C2—C3—Cl1	−179.2 (3)	N1—C7—C8—C9	−178.4 (3)
C2—C3—C4—C5	0.0 (6)	C7—C8—C9—C10	−71.0 (4)
Cl1—C3—C4—C5	178.8 (3)	C8—C9—C10—O2	−18.4 (5)
C3—C4—C5—C6	0.1 (6)	C8—C9—C10—O3	162.3 (3)
C2—C1—C6—C5	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1i	0.82 (2)	1.92 (2)	2.693 (3)	158 (5)
N1—H1N···O2ii	0.85 (2)	2.02 (2)	2.872 (4)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O1i	0.82 (2)	1.92 (2)	2.693 (3)	158 (5)
N1—H1N⋯O2ii	0.85 (2)	2.02 (2)	2.872 (4)	173 (3)

Symmetry codes: (i) ; (ii) .