N-(2,6-Dichloro-phen-yl)succinamic acid.

In the crystal of the title compound, C(10)H(9)Cl(2)NO(3), the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the H atoms on the adjacent -CH(2) groups. The C=O and O-H bonds of the acid group are syn to one another. In the crystal, mol-ecules are packed into infinite chains through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For our studies of the effect of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2000 ▶, 2009 ▶). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). For packing of mol­ecules involving dimeric hydrogen-bonding associations of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C10H9Cl2NO3

M = 262.08

Monoclinic,

a = 4.713 (1) Å

b = 11.963 (3) Å

c = 20.687 (4) Å

β = 94.64 (2)°

V = 1162.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.55 mm−1

T = 293 K

0.48 × 0.06 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.779, T max = 0.978

3912 measured reflections

1965 independent reflections

1189 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.119

wR(F 2) = 0.222

S = 1.34

1965 reflections

145 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024949/sj5173sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024949/sj5173Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024949/sj5173Isup3.cml

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

C10H9Cl2NO3	F(000) = 536
Mr = 262.08	Dx = 1.497 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 777 reflections
a = 4.713 (1) Å	θ = 3.0–27.7°
b = 11.963 (3) Å	µ = 0.55 mm−1
c = 20.687 (4) Å	T = 293 K
β = 94.64 (2)°	Needle, colourless
V = 1162.5 (4) Å3	0.48 × 0.06 × 0.04 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1965 independent reflections
Radiation source: fine-focus sealed tube	1189 reflections with I > 2σ(I)
graphite	Rint = 0.052
Rotation method data acquisition using ω scans	θmax = 25.2°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→5
Tmin = 0.779, Tmax = 0.978	k = −12→14
3912 measured reflections	l = −16→24

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)] = 0.119	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222	H-atom parameters constrained
S = 1.34	w = 1/[σ2(Fo2) + (0.P)2 + 8.7677P] where P = (Fo2 + 2Fc2)/3
1965 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.57 e Å−3
18 restraints	Δρmin = −0.55 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	0.5925 (18)	0.1082 (7)	0.3449 (4)	0.028 (2)
C2	0.4791 (19)	0.1566 (8)	0.2870 (5)	0.039 (2)
C3	0.554 (2)	0.2620 (8)	0.2688 (5)	0.049 (3)
H3	0.4712	0.2925	0.2304	0.059*
C4	0.749 (3)	0.3227 (9)	0.3068 (6)	0.063 (4)
H4	0.8010	0.3938	0.2938	0.076*
C5	0.871 (2)	0.2786 (9)	0.3643 (6)	0.058 (3)
H5	1.0064	0.3186	0.3899	0.069*
C6	0.785 (2)	0.1730 (8)	0.3832 (5)	0.041 (3)
C7	0.6868 (18)	−0.0859 (7)	0.3757 (4)	0.027 (2)
C8	0.5518 (18)	−0.1883 (8)	0.4030 (5)	0.039 (2)
H8A	0.3759	−0.2043	0.3771	0.047*
H8B	0.5035	−0.1716	0.4467	0.047*
C9	0.7363 (19)	−0.2911 (7)	0.4051 (4)	0.034 (2)
H9A	0.7487	−0.3182	0.3613	0.041*
H9B	0.9269	−0.2711	0.4225	0.041*
C10	0.627 (2)	−0.3827 (8)	0.4453 (5)	0.044 (3)
N1	0.5076 (14)	0.0022 (6)	0.3650 (3)	0.0312 (18)
H1N	0.3308	−0.0076	0.3709	0.037*
O1	0.9365 (12)	−0.0820 (5)	0.3658 (3)	0.0348 (16)
O2	0.738 (2)	−0.4776 (7)	0.4371 (4)	0.095 (3)
H2O	0.6475	−0.5255	0.4551	0.114*
O3	0.460 (2)	−0.3676 (7)	0.4844 (4)	0.089 (3)
Cl1	0.2395 (6)	0.0781 (3)	0.23715 (14)	0.0625 (9)
Cl2	0.9252 (7)	0.1234 (3)	0.45814 (13)	0.0621 (9)

	U11	U22	U33	U12	U13	U23
C1	0.024 (5)	0.017 (5)	0.046 (6)	0.003 (4)	0.012 (4)	−0.001 (4)
C2	0.033 (6)	0.038 (6)	0.047 (6)	0.006 (5)	0.007 (5)	0.009 (5)
C3	0.061 (7)	0.032 (6)	0.059 (7)	0.012 (6)	0.026 (6)	0.020 (6)
C4	0.074 (9)	0.024 (6)	0.096 (10)	−0.002 (6)	0.030 (8)	0.006 (7)
C5	0.062 (8)	0.028 (6)	0.083 (9)	−0.003 (6)	0.009 (7)	−0.003 (6)
C6	0.045 (6)	0.029 (6)	0.051 (7)	0.012 (5)	0.017 (5)	0.002 (5)
C7	0.023 (5)	0.023 (5)	0.035 (5)	−0.003 (4)	0.000 (4)	0.004 (4)
C8	0.025 (5)	0.031 (6)	0.059 (7)	0.001 (4)	0.000 (5)	0.016 (5)
C9	0.032 (5)	0.030 (5)	0.042 (6)	−0.003 (4)	0.013 (4)	0.002 (4)
C10	0.048 (6)	0.022 (5)	0.065 (7)	0.021 (5)	0.025 (5)	0.015 (5)
N1	0.019 (4)	0.027 (4)	0.049 (5)	−0.003 (3)	0.010 (3)	0.014 (3)
O1	0.018 (3)	0.028 (4)	0.059 (4)	−0.001 (3)	0.011 (3)	0.005 (3)
O2	0.119 (7)	0.057 (5)	0.120 (6)	0.012 (5)	0.075 (5)	0.031 (5)
O3	0.112 (6)	0.048 (5)	0.116 (6)	0.021 (5)	0.068 (5)	0.028 (5)
Cl1	0.0596 (18)	0.063 (2)	0.0619 (19)	0.0017 (16)	−0.0145 (14)	0.0092 (15)
Cl2	0.080 (2)	0.0543 (18)	0.0492 (17)	0.0067 (16)	−0.0129 (15)	−0.0084 (15)

C1—C6	1.392 (13)	C7—N1	1.358 (10)
C1—C2	1.396 (12)	C7—C8	1.511 (12)
C1—N1	1.402 (10)	C8—C9	1.505 (12)
C2—C3	1.370 (13)	C8—H8A	0.9700
C2—Cl1	1.741 (10)	C8—H8B	0.9700
C3—C4	1.370 (15)	C9—C10	1.491 (12)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.382 (15)	C9—H9B	0.9700
C4—H4	0.9300	C10—O3	1.190 (11)
C5—C6	1.391 (14)	C10—O2	1.266 (11)
C5—H5	0.9300	N1—H1N	0.8600
C6—Cl2	1.739 (10)	O2—H2O	0.8200
C7—O1	1.212 (9)
C6—C1—C2	116.4 (8)	N1—C7—C8	114.5 (7)
C6—C1—N1	121.6 (8)	C7—C8—C9	114.4 (7)
C2—C1—N1	122.0 (8)	C7—C8—H8A	108.7
C3—C2—C1	121.9 (10)	C9—C8—H8A	108.7
C3—C2—Cl1	120.1 (8)	C7—C8—H8B	108.7
C1—C2—Cl1	118.0 (7)	C9—C8—H8B	108.7
C2—C3—C4	120.4 (11)	H8A—C8—H8B	107.6
C2—C3—H3	119.8	C10—C9—C8	113.1 (7)
C4—C3—H3	119.8	C10—C9—H9A	109.0
C3—C4—C5	120.2 (11)	C8—C9—H9A	109.0
C3—C4—H4	119.9	C10—C9—H9B	109.0
C5—C4—H4	119.9	C8—C9—H9B	109.0
C4—C5—C6	118.7 (11)	H9A—C9—H9B	107.8
C4—C5—H5	120.7	O3—C10—O2	121.9 (9)
C6—C5—H5	120.7	O3—C10—C9	123.1 (9)
C5—C6—C1	122.4 (10)	O2—C10—C9	114.9 (8)
C5—C6—Cl2	117.6 (9)	C7—N1—C1	124.2 (7)
C1—C6—Cl2	120.0 (7)	C7—N1—H1N	117.9
O1—C7—N1	122.9 (8)	C1—N1—H1N	117.9
O1—C7—C8	122.6 (8)	C10—O2—H2O	109.5
C6—C1—C2—C3	0.2 (13)	C2—C1—C6—Cl2	176.8 (7)
N1—C1—C2—C3	177.3 (8)	N1—C1—C6—Cl2	−0.4 (12)
C6—C1—C2—Cl1	179.4 (7)	O1—C7—C8—C9	−11.0 (13)
N1—C1—C2—Cl1	−3.4 (11)	N1—C7—C8—C9	170.9 (8)
C1—C2—C3—C4	1.5 (15)	C7—C8—C9—C10	167.1 (9)
Cl1—C2—C3—C4	−177.8 (8)	C8—C9—C10—O3	−18.2 (16)
C2—C3—C4—C5	−0.9 (17)	C8—C9—C10—O2	165.2 (10)
C3—C4—C5—C6	−1.3 (17)	O1—C7—N1—C1	−3.5 (14)
C4—C5—C6—C1	3.1 (15)	C8—C7—N1—C1	174.5 (8)
C4—C5—C6—Cl2	−176.2 (8)	C6—C1—N1—C7	−62.7 (12)
C2—C1—C6—C5	−2.5 (13)	C2—C1—N1—C7	120.3 (10)
N1—C1—C6—C5	−179.6 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.06	2.875 (9)	159
O2—H2O···O3ii	0.82	1.89	2.678 (11)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.06	2.875 (9)	159
O2—H2O⋯O3ii	0.82	1.89	2.678 (11)	162

Symmetry codes: (i) ; (ii) .