N-(2-Chloro-phen-yl)succinamic acid.

The conformations of the N-H and C=O bonds in the amide segment of the structure of the title compound {systematic name: 3-[(2-chloro-phen-yl)amino-carbon-yl]propionic acid}, C(10)H(10)ClNO(3), are trans to each other, while the conformation of the amide H atom is syn to the ortho-chloro group in the benzene ring. Further, the conformations of the amide O atom and the carbonyl O atom of the ester segment are also trans to the H atoms attached to the adjacent C atoms. In the crystal structure, mol-ecules are packed into infinite chains through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For general background see: Gowda, Kozisek et al. (2007 ▶); Gowda, Svoboda et al. (2007 ▶); Gowda et al. (2008 ▶); Jones et al. (1990 ▶); Wan et al. (2006 ▶).

Experimental

Crystal data

C10H10ClNO3

M = 227.64

Monoclinic,

a = 4.9056 (5) Å

b = 11.126 (1) Å

c = 18.677 (2) Å

β = 94.92 (1)°

V = 1015.63 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 299 (2) K

0.50 × 0.35 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.840, T max = 0.899

6644 measured reflections

2065 independent reflections

1585 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.126

S = 1.08

2065 reflections

142 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002979/xu2474sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002979/xu2474Isup2.hkl

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

C10H10ClNO3	F(000) = 472
Mr = 227.64	Dx = 1.489 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2963 reflections
a = 4.9056 (5) Å	θ = 2.2–28.0°
b = 11.126 (1) Å	µ = 0.36 mm−1
c = 18.677 (2) Å	T = 299 K
β = 94.92 (1)°	Rod, colourless
V = 1015.63 (18) Å3	0.50 × 0.35 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2065 independent reflections
Radiation source: fine-focus sealed tube	1585 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −6→6
Tmin = 0.840, Tmax = 0.899	k = −13→13
6644 measured reflections	l = −23→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.3374P] where P = (Fo2 + 2Fc2)/3
2065 reflections	(Δ/σ)max = 0.013
142 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.21 e Å−3

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	−0.0798 (3)	0.18091 (17)	0.84736 (10)	0.0321 (4)
C2	0.0342 (4)	0.22834 (17)	0.78777 (10)	0.0344 (4)
C3	−0.0244 (4)	0.34392 (19)	0.76422 (12)	0.0443 (5)
H3	0.0569	0.3749	0.7250	0.053*
C4	−0.2039 (5)	0.4129 (2)	0.79921 (14)	0.0511 (6)
H4	−0.2443	0.4907	0.7835	0.061*
C5	−0.3238 (4)	0.36726 (19)	0.85722 (13)	0.0486 (6)
H5	−0.4482	0.4137	0.8800	0.058*
C6	−0.2601 (4)	0.25260 (19)	0.88184 (11)	0.0401 (5)
H6	−0.3387	0.2232	0.9219	0.048*
C7	−0.1818 (4)	−0.01912 (17)	0.89519 (10)	0.0337 (4)
C8	−0.0514 (4)	−0.13863 (18)	0.91553 (12)	0.0421 (5)
H8A	0.0103	−0.1762	0.8729	0.051*
H8B	0.1076	−0.1253	0.9491	0.051*
C9	−0.2446 (4)	−0.2219 (2)	0.94887 (14)	0.0507 (6)
H9A	−0.4053	−0.2326	0.9154	0.061*
H9B	−0.3036	−0.1838	0.9916	0.061*
C10	−0.1304 (4)	−0.34338 (18)	0.96916 (11)	0.0392 (5)
N1	−0.0075 (3)	0.06395 (15)	0.87205 (9)	0.0369 (4)
H1N	0.165 (3)	0.042 (2)	0.8730 (12)	0.044*
O1	−0.4257 (3)	−0.00054 (13)	0.89803 (9)	0.0479 (4)
O2	−0.2733 (3)	−0.40550 (16)	1.00881 (11)	0.0614 (5)
H2O	−0.201 (6)	−0.469 (2)	1.0217 (15)	0.074*
O3	0.0897 (3)	−0.37797 (14)	0.94783 (10)	0.0559 (5)
Cl1	0.25199 (11)	0.14183 (5)	0.74014 (3)	0.0493 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0253 (8)	0.0311 (9)	0.0396 (10)	−0.0008 (7)	0.0003 (7)	0.0032 (8)
C2	0.0285 (9)	0.0339 (10)	0.0410 (10)	−0.0015 (8)	0.0040 (8)	0.0008 (8)
C3	0.0442 (12)	0.0387 (11)	0.0505 (12)	−0.0035 (9)	0.0066 (9)	0.0119 (9)
C4	0.0496 (13)	0.0318 (11)	0.0715 (15)	0.0065 (9)	0.0036 (11)	0.0102 (11)
C5	0.0405 (12)	0.0387 (12)	0.0673 (15)	0.0077 (9)	0.0080 (10)	−0.0066 (10)
C6	0.0366 (10)	0.0419 (11)	0.0426 (10)	0.0020 (9)	0.0088 (8)	0.0008 (9)
C7	0.0285 (9)	0.0357 (10)	0.0374 (10)	0.0009 (8)	0.0047 (7)	0.0075 (8)
C8	0.0321 (10)	0.0372 (11)	0.0583 (13)	0.0034 (8)	0.0105 (9)	0.0143 (10)
C9	0.0361 (11)	0.0423 (12)	0.0748 (15)	0.0018 (9)	0.0106 (10)	0.0231 (11)
C10	0.0317 (10)	0.0382 (11)	0.0477 (11)	−0.0020 (8)	0.0034 (8)	0.0095 (9)
N1	0.0248 (7)	0.0341 (9)	0.0524 (10)	0.0042 (7)	0.0069 (7)	0.0105 (8)
O1	0.0256 (7)	0.0444 (8)	0.0743 (11)	0.0026 (6)	0.0084 (6)	0.0169 (8)
O2	0.0516 (10)	0.0441 (9)	0.0918 (13)	0.0046 (7)	0.0255 (9)	0.0298 (9)
O3	0.0512 (9)	0.0477 (9)	0.0719 (11)	0.0098 (7)	0.0228 (8)	0.0196 (8)
Cl1	0.0475 (3)	0.0468 (3)	0.0566 (4)	0.0016 (2)	0.0224 (2)	−0.0006 (2)

C1—C6	1.390 (3)	C7—N1	1.355 (2)
C1—C2	1.392 (3)	C7—C8	1.510 (3)
C1—N1	1.416 (2)	C8—C9	1.498 (3)
C2—C3	1.381 (3)	C8—H8A	0.9700
C2—Cl1	1.7385 (19)	C8—H8B	0.9700
C3—C4	1.375 (3)	C9—C10	1.500 (3)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.373 (3)	C9—H9B	0.9700
C4—H4	0.9300	C10—O3	1.243 (2)
C5—C6	1.383 (3)	C10—O2	1.267 (2)
C5—H5	0.9300	N1—H1N	0.877 (16)
C6—H6	0.9300	O2—H2O	0.814 (18)
C7—O1	1.220 (2)
C6—C1—C2	117.93 (17)	N1—C7—C8	114.57 (15)
C6—C1—N1	121.89 (17)	C9—C8—C7	112.30 (16)
C2—C1—N1	120.17 (17)	C9—C8—H8A	109.1
C3—C2—C1	121.38 (18)	C7—C8—H8A	109.1
C3—C2—Cl1	118.22 (15)	C9—C8—H8B	109.1
C1—C2—Cl1	120.40 (15)	C7—C8—H8B	109.1
C4—C3—C2	119.5 (2)	H8A—C8—H8B	107.9
C4—C3—H3	120.2	C8—C9—C10	115.23 (17)
C2—C3—H3	120.2	C8—C9—H9A	108.5
C5—C4—C3	120.3 (2)	C10—C9—H9A	108.5
C5—C4—H4	119.9	C8—C9—H9B	108.5
C3—C4—H4	119.9	C10—C9—H9B	108.5
C4—C5—C6	120.23 (19)	H9A—C9—H9B	107.5
C4—C5—H5	119.9	O3—C10—O2	123.9 (2)
C6—C5—H5	119.9	O3—C10—C9	120.93 (18)
C5—C6—C1	120.66 (19)	O2—C10—C9	115.21 (18)
C5—C6—H6	119.7	C7—N1—C1	125.72 (15)
C1—C6—H6	119.7	C7—N1—H1N	115.9 (15)
O1—C7—N1	123.12 (18)	C1—N1—H1N	118.4 (15)
O1—C7—C8	122.29 (17)	C10—O2—H2O	113 (2)
C6—C1—C2—C3	1.4 (3)	N1—C1—C6—C5	178.97 (19)
N1—C1—C2—C3	−177.44 (18)	O1—C7—C8—C9	−8.3 (3)
C6—C1—C2—Cl1	−177.74 (14)	N1—C7—C8—C9	173.18 (19)
N1—C1—C2—Cl1	3.5 (3)	C7—C8—C9—C10	178.86 (19)
C1—C2—C3—C4	−1.5 (3)	C8—C9—C10—O3	−12.2 (3)
Cl1—C2—C3—C4	177.60 (17)	C8—C9—C10—O2	167.7 (2)
C2—C3—C4—C5	0.1 (3)	O1—C7—N1—C1	−1.0 (3)
C3—C4—C5—C6	1.4 (4)	C8—C7—N1—C1	177.49 (18)
C4—C5—C6—C1	−1.6 (3)	C6—C1—N1—C7	42.4 (3)
C2—C1—C6—C5	0.2 (3)	C2—C1—N1—C7	−138.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.88 (2)	2.08 (2)	2.943 (2)	168 (2)
O2—H2O···O3ii	0.81 (2)	1.87 (2)	2.673 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.877 (16)	2.079 (17)	2.943 (2)	168 (2)
O2—H2O⋯O3ii	0.814 (18)	1.866 (18)	2.673 (2)	171 (3)

Symmetry codes: (i) ; (ii) .