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Acta Crystallogr Sect E Struct Rep OnlineActa Cryst. EActa Crystallographica Section E: Structure Reports Online1600-5368International Union of Crystallography sj517310.1107/S1600536811024949ACSEBHS1600536811024949Organic Papers
               N-(2,6-Dichloro­phen­yl)succinamic acid C10H9Cl2NO3Saraswathi B. S. aForo Sabine bGowda B. Thimme a*a Department of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, Indiab Institute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, GermanyCorrespondence e-mail: nguyenkaren@example.org 8 2011 02 7 2011 02 7 2011 67 Pt 8 e110800o1880 o1880 22 6 2011 25 6 2011 © Saraswathi et al. 20112011This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.A full version of this article is available from Crystallography Journals Online.In the crystal of the title compound, C10H9Cl2NO3, 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 –CH2 groups. The C=O and O—H bonds of the acid group are syn to one another. In the crystal, mol­ecules are packed into infinite chains through inter­molecular O—H⋯O and N—H⋯O hydrogen bonds.
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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 ▶, 2009a ▶,b
             ▶). 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
                           r = 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.

Supplementary Material
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
            

 Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5173).

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic 
information

Comment 
The amide moiety is an important constituent of many biologically important
compounds. As part of our studies into the substituent effects on the
structures and other aspects of this class of compounds (Bhat & Gowda,
2000;
Gowda et al., 2000, 2009a,b), in
the present work, the crystal
structure of N-(2,6-dichlorophenyl)-succinamic acid (I) has been
determined (Fig. 1). The conformation of the amide O atom and the carbonyl O
atom of the acid segment are anti to each other and are also
anti to the H atoms attached to the adjacent C atoms (Fig.1). Further,
C=O and O—H bonds of the acid group are syn to each other, similar to
that observed in N-(2-chlorophenyl)-succinamic acid (Gowda et
al., 2009a) and N-(2,6-dimethylphenyl)-succinamic
acid
(Gowda et al., 2009b).

In the structure, the intermolecular O—H···O and N—H···O hydrogen bonds
pack the molecules into infinite chains (Table 1, Fig.2).

The modes of interlinking carboxylic acids by hydrogen bonds is described
elsewhere (Leiserowitz, 1976). The packing of molecules involving
dimeric
hydrogen bonded association of each carboxyl group with a centrosymmetrically
related neighbor has also been observed (Jagannathan et al.,
1994).


Experimental 
A solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated
dropwise with the solution of 2,6-dichloroaniline (0.01 mole) also in toluene
(20 ml) with constant stirring. The resulting mixture was stirred for about
one hour and set aside for an additional hour at room temperature for
completion of the reaction. The mixture was then treated with dilute
hydrochloric acid to remove the unreacted 2,6-dichloroaniline. The resultant
title compound was filtered under suction and washed thoroughly with water to
remove the unreacted succinic anhydride and succinic acid. It was
recrystallized to constant melting point from ethanol. The purity of the
compound was checked and characterized by its infrared and NMR spectra.

Colorless needle like single crystals used in X-ray diffraction studies were
grown in ethanolic solution by slow evaporation at room temperature.


Refinement 
The H atoms were positioned with idealized geometry using a riding model with
the aromatic C—H = 0.93 Å, methylene C—H = 0.97 Å, N—H = 0.86 Å
and O—H = 0.82 Å, and were refined with isotropic displacement parameters
(set to 1.2 times of the Ueq of the parent atom).

The crystals available for X-ray analysis were of rather poor quality and weak
scatterers at high theta value with very low intensity, resulting in
relatively high R values. The crystal has 37.1% weak reflections.

Figures
Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.

Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Crystal data
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		
Data collection
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
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	
Special details
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.	
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
	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)		
Atomic displacement parameters (Å2)
	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)	
Geometric parameters (Å, °)
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)			
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) x−1, y, z; (ii) −x+1, −y−1, −z+1.

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) .
==== Refs
References
Bhat, D. K. & Gowda, B. T. (2000). J. Indian Chem. Soc. 
               77, 279–284.
Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009a). Acta Cryst. E65, o399.
Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o466.
Gowda, B. T., Kumar, B. H. A. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 721–728.
Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 
               24, 75–78.
Leiserowitz, L. (1976). Acta Cryst. B32, 775–802.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.


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