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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1130.
Published online 2009 April 25. doi:  10.1107/S1600536809015025
PMCID: PMC2977803

3-[(3,4-Dichloro­phen­yl)amino­carbon­yl]propionic acid

Abstract

In the title compound, C10H9Cl2NO3, inversion dimers occur due to pairs of inter­molecular O—H(...)O hydrogen bonds from the carboxyl groups forming R 2 2(8) loops. The dimers are linked into C(4) chains along the a axis by inter­molecular N—H(...)O links. A short intra­molecular C—H(...)O contact occurs in the mol­ecule.

Related literature

For a related structure, see: Shah et al. (2008 [triangle]). For background, see: Pellerito & Nagy (2002 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o1130-scheme1.jpg

Experimental

Crystal data

  • C10H9Cl2NO3
  • M r = 262.08
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1130-efi1.jpg
  • a = 4.8441 (4) Å
  • b = 10.3388 (10) Å
  • c = 22.457 (2) Å
  • β = 90.613 (3)°
  • V = 1124.62 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.57 mm−1
  • T = 296 K
  • 0.25 × 0.12 × 0.10 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.925, T max = 0.949
  • 11915 measured reflections
  • 2912 independent reflections
  • 2028 reflections with I > 3σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.182
  • S = 1.05
  • 2912 reflections
  • 172 parameters
  • Only H-atom coordinates refined
  • Δρmax = 0.89 e Å−3
  • Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015025/hb2958sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015025/hb2958Isup2.hkl

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

Acknowledgments

The authors acknowledge the the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore. S. Ali is also grateful to the PSF for financial support under project No. PSF/R&D/C–QU/Chem(270).

supplementary crystallographic information

Comment

In order to get a better insight in how the metallic species behave inside the biological systems, it is necessary to study their coordination behavior with biomolecules i.e. ligands having hetero-donor oxygen and nitrogen atoms (Pellerito & Nagy, 2002). Therefore, the title compound (I) has been prepared for the study of complexation with different metals.

The title compound is the structural isomer of 3-(3,5-dichloroanilinocarbonyl) propionic acid (Shah et al., 2008). Due to the change of chloro substitution, the packing of the title compound has been changed. In this structure there does not exist any kind of π-interaction. The dimeric nature and the linkage of the dimers in title compound is in agreement with the reported structural isomer. In (I) the C==O bond distances for carboxylate and carbonyl group have values of (C10==O2: 1.236 (3) Å) and (C7==O3: 1.214 (3) Å), and in comparison to 1.219 (3) and 1.225 (2) Å, respectively. The C—N bond distances are compareable within experimental errors. In both compounds similar intermolecular H-bonding (Table 2, Fig. 2) has been observed. The dihedral angle between the aromatic ring (C1—C6) and (C8—C10/O1/O2) have a value of 20.45 (20)°, whereas with (C1/N1/C7/O3) its value is 39.02 (16)°. The value of dihedral angle between (C8—C10/O1/O2) and (C1/N1/C7/O3) is 18.69 (18)°. There exist an intramolecular H-bond of C—H···O type and completes a six-membered heterocyclic ring adjacent to the benzene ring. There does not exist any kind of π-interactions.

Experimental

3,4-dichloroanilline (16.2 g, 0.1 mol) and succinic anhydride (10 g, 0.1 mole) were mixed in glacial acetic acid and stirred overnight. The solution was filtered and precipitated material was washed with distilled water. The acid formed was recrystallized from acetone to yield colourless blocks of (I). (Yield: 80%).

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small spheres of arbitrary radius. The dashed lines represent the intramolecular H-bonds.
Fig. 2.
The partial unit cell packing of (I) showing the dimeric nature and the linkage of dimers along the a axis.

Crystal data

C10H9Cl2NO3F(000) = 536
Mr = 262.08Dx = 1.548 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2912 reflections
a = 4.8441 (4) Åθ = 2.7–28.9°
b = 10.3388 (10) ŵ = 0.57 mm1
c = 22.457 (2) ÅT = 296 K
β = 90.613 (3)°Block, colourless
V = 1124.62 (17) Å30.25 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer2912 independent reflections
Radiation source: fine-focus sealed tube2028 reflections with I > 3σ(I)
graphiteRint = 0.028
Detector resolution: 7.5 pixels mm-1θmax = 28.9°, θmin = 2.7°
ω scansh = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −13→13
Tmin = 0.925, Tmax = 0.949l = −30→30
11915 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182Only H-atom coordinates refined
S = 1.05w = 1/[σ2(Fo2) + (0.0667P)2 + 1.6338P] where P = (Fo2 + 2Fc2)/3
2912 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = −0.84 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
Cl10.2707 (3)0.56808 (11)0.26822 (5)0.0954 (5)
Cl20.6942 (3)0.37607 (10)0.20648 (6)0.0945 (5)
O10.7844 (5)1.3991 (2)−0.01026 (13)0.0584 (9)
O20.4038 (4)1.3685 (2)0.04204 (12)0.0551 (8)
O30.9245 (4)0.9675 (2)0.08819 (12)0.0546 (8)
N10.4948 (5)0.9009 (2)0.11088 (11)0.0372 (7)
C10.5572 (5)0.7772 (3)0.13420 (12)0.0341 (8)
C20.4079 (7)0.7353 (3)0.18269 (14)0.0427 (9)
C30.4538 (8)0.6133 (3)0.20585 (14)0.0500 (10)
C40.6432 (8)0.5320 (3)0.18016 (16)0.0543 (11)
C50.7934 (8)0.5742 (3)0.13222 (18)0.0568 (11)
C60.7517 (7)0.6968 (3)0.10907 (15)0.0448 (9)
C70.6785 (5)0.9883 (3)0.09118 (12)0.0345 (8)
C80.5505 (6)1.1164 (3)0.07282 (17)0.0438 (9)
C90.7506 (6)1.2040 (3)0.04237 (17)0.0437 (9)
C100.6312 (5)1.3316 (3)0.02430 (13)0.0384 (8)
H1N0.334 (7)0.922 (3)0.1111 (15)0.0447*
H1O0.722 (9)1.470 (4)−0.0157 (19)0.0701*
H20.278 (7)0.793 (4)0.2003 (15)0.0513*
H50.939 (8)0.518 (4)0.1166 (17)0.0680*
H60.846 (7)0.722 (4)0.0777 (16)0.0537*
H8A0.489 (8)1.153 (4)0.1063 (16)0.0527*
H8B0.377 (8)1.101 (3)0.0478 (15)0.0527*
H9A0.899 (7)1.225 (4)0.0680 (16)0.0523*
H9B0.840 (7)1.164 (4)0.0077 (16)0.0523*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1600 (13)0.0566 (6)0.0704 (7)−0.0127 (7)0.0418 (7)0.0207 (5)
Cl20.1284 (11)0.0363 (5)0.1187 (10)0.0107 (6)−0.0093 (8)0.0277 (5)
O10.0476 (13)0.0356 (12)0.0924 (19)0.0084 (10)0.0234 (12)0.0257 (12)
O20.0400 (11)0.0410 (12)0.0846 (17)0.0114 (9)0.0176 (11)0.0226 (11)
O30.0251 (10)0.0418 (12)0.0969 (18)0.0059 (8)0.0058 (10)0.0219 (12)
N10.0260 (10)0.0317 (12)0.0541 (14)0.0044 (9)0.0040 (10)0.0114 (10)
C10.0337 (13)0.0263 (12)0.0423 (14)−0.0008 (10)−0.0030 (10)0.0043 (10)
C20.0540 (17)0.0294 (13)0.0449 (16)−0.0031 (12)0.0066 (13)0.0006 (12)
C30.073 (2)0.0331 (15)0.0440 (16)−0.0104 (14)0.0021 (15)0.0056 (12)
C40.072 (2)0.0276 (14)0.063 (2)0.0001 (14)−0.0119 (17)0.0098 (14)
C50.059 (2)0.0345 (16)0.077 (2)0.0123 (15)0.0027 (18)0.0006 (16)
C60.0445 (16)0.0358 (15)0.0542 (18)0.0066 (12)0.0086 (13)0.0038 (13)
C70.0279 (12)0.0302 (13)0.0455 (14)0.0028 (10)0.0029 (10)0.0078 (11)
C80.0307 (14)0.0320 (14)0.069 (2)0.0075 (11)0.0112 (13)0.0165 (14)
C90.0319 (14)0.0315 (14)0.068 (2)0.0042 (11)0.0091 (13)0.0137 (13)
C100.0305 (13)0.0305 (13)0.0543 (16)0.0010 (10)0.0021 (11)0.0090 (12)

Geometric parameters (Å, °)

Cl1—C31.730 (4)C4—C51.377 (5)
Cl2—C41.734 (3)C5—C61.384 (5)
O1—C101.286 (4)C7—C81.518 (4)
O2—C101.236 (3)C8—C91.497 (5)
O3—C71.214 (3)C9—C101.495 (4)
O1—H1O0.80 (4)C2—H20.96 (4)
N1—C11.414 (4)C5—H50.98 (4)
N1—C71.346 (4)C6—H60.88 (4)
N1—H1N0.81 (3)C8—H8A0.90 (4)
C1—C61.382 (4)C8—H8B1.02 (4)
C1—C21.383 (4)C9—H9A0.94 (4)
C2—C31.382 (4)C9—H9B0.99 (4)
C3—C41.376 (5)
C10—O1—H1O112 (3)C8—C9—C10114.0 (2)
C1—N1—C7126.1 (2)O1—C10—O2123.3 (3)
C7—N1—H1N117 (2)O1—C10—C9114.8 (2)
C1—N1—H1N116 (2)O2—C10—C9121.9 (3)
N1—C1—C6122.5 (3)C1—C2—H2119 (2)
N1—C1—C2117.6 (3)C3—C2—H2121 (2)
C2—C1—C6119.9 (3)C4—C5—H5119 (2)
C1—C2—C3119.9 (3)C6—C5—H5121 (2)
Cl1—C3—C2118.0 (3)C1—C6—H6121 (3)
C2—C3—C4120.4 (3)C5—C6—H6120 (3)
Cl1—C3—C4121.6 (3)C7—C8—H8A106 (3)
C3—C4—C5119.7 (3)C7—C8—H8B110.2 (18)
Cl2—C4—C5119.1 (3)C9—C8—H8A111 (3)
Cl2—C4—C3121.2 (3)C9—C8—H8B112.2 (19)
C4—C5—C6120.5 (3)H8A—C8—H8B104 (3)
C1—C6—C5119.7 (3)C8—C9—H9A111 (2)
O3—C7—N1123.5 (3)C8—C9—H9B114 (2)
O3—C7—C8122.6 (3)C10—C9—H9A105 (2)
N1—C7—C8113.9 (2)C10—C9—H9B109 (2)
C7—C8—C9112.8 (2)H9A—C9—H9B104 (3)
C7—N1—C1—C2140.0 (3)Cl1—C3—C4—C5−177.0 (3)
C7—N1—C1—C6−42.4 (4)C2—C3—C4—Cl2−177.3 (3)
C1—N1—C7—O34.2 (5)C2—C3—C4—C52.0 (5)
C1—N1—C7—C8−175.8 (3)Cl2—C4—C5—C6178.1 (3)
N1—C1—C2—C3177.7 (3)C3—C4—C5—C6−1.2 (6)
C6—C1—C2—C30.0 (5)C4—C5—C6—C1−0.2 (5)
N1—C1—C6—C5−176.8 (3)O3—C7—C8—C99.0 (5)
C2—C1—C6—C50.8 (5)N1—C7—C8—C9−171.0 (3)
C1—C2—C3—Cl1177.6 (2)C7—C8—C9—C10−179.4 (3)
C1—C2—C3—C4−1.4 (5)C8—C9—C10—O1−169.1 (3)
Cl1—C3—C4—Cl23.7 (5)C8—C9—C10—O211.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.81 (3)2.10 (3)2.887 (3)165 (3)
O1—H1O···O2ii0.80 (4)1.87 (4)2.665 (3)170 (4)
C6—H6···O30.88 (4)2.58 (4)2.960 (4)107 (3)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+3, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2958).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Pellerito, L. & Nagy, L. (2002). Coord. Chem. Rev.224, 111–150.
  • Shah, F. A., Tahir, M. N., Ali, S. & Kashmiri, M. A. (2008). Acta Cryst. E64, o787. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography