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N,N′-Bis(3-chloro­phen­yl)succinamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 16 March 2011; accepted 20 March 2011; online 26 March 2011)

The complete molecule of the title compound, C16H14Cl2N2O2, is generated by crystallographic inversion symmetry. The dihedral angle between the benzene ring and the NH—C(O)—C fragment is 32.8 (1)°. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds into [100] chains.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000[Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791-800.]); Saraswathi et al. (2011[Saraswathi, B. S., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o607.]), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.]) and of N-(substitutedphen­yl)-p-substituted-benzene­sulfonamides, see: Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14Cl2N2O2

  • Mr = 337.19

  • Monoclinic, P 21 /c

  • a = 8.3412 (8) Å

  • b = 9.6501 (9) Å

  • c = 9.5485 (9) Å

  • β = 91.319 (9)°

  • V = 768.39 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 293 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.847, Tmax = 0.919

  • 2574 measured reflections

  • 1535 independent reflections

  • 1253 reflections with I > 2σ(I)

  • Rint = 0.009

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.105

  • S = 1.07

  • 1535 reflections

  • 103 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.81 (2) 2.10 (2) 2.8946 (19) 166 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The amide and sulfonamide moieties are important constituents of many biologically significant compounds. As a part of studying the substituent effects on the structures of this class of compounds(Gowda et al., 2000, 2005, 2007; Saraswathi et al., 2011), in the present work, the structure of N,N-bis(3-chlorophenyl)-succinamide (I) has been determined (Fig.1). The conformations of N—H and C=O bonds in the C—NH—C(O)—C segments are anti to each other and the amide O atoms are anti to the H atoms attached to the adjacent C atoms. Further, conformations of the N—H bonds in the amide fragments are anti to the meta-chloro groups in the adjacent benzene rings, similar to the anti conformations observed with respect to the ortho-methyl groups in N,N-bis(2-methylphenyl)- succinamide (II) (Saraswathi et al., 2011). The dihedral angle between the benzene ring and the NH—C(O)—CH2 segment in the two halves of the molecule is 32.8 (1)°, compared to the value of 62.1 (2)° in (II).

Further, C1—N1—C7—C8 and C1a—N1a—C7a—C8a segments in (I) are nearly linear and so also the C1—N1—C7—O1 and C1a—N1a—C7a—O1a segments, similar to those observed in (II). The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are -35.0 (3)° and 147.5 (2)°, in contrast to the values of -64.0 (4)° and 117.6 (3)° in (II).

The packing of molecules in the crystal linked by of N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2000); Saraswathi et al. (2011), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-(substitutedphenyl)-p-substituted-benzenesulfonamides, see: Gowda et al. (2005).

Experimental top

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with 3-chloroaniline (0.01 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for 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 unreacted 3-chloroaniline. The resultant solid N-(3-chlorophenyl)-succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. The compound was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

The N-(3-chlorophenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of 3-chloroaniline at room temperature with constant stirring. The resultant mixture was stirred for 4 h, kept aside for additional 6 h for completion of the reaction and poured slowly into crushed ice with constant stirring. It was kept aside for a day. The resultant solid, N,N-bis(3-chlorophenyl)- succinamide was filtered under suction, washed thoroughly with water, dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from a mixture of acetone and chloroform. The purity of the compound was checked by elemental analysis, and characterized by its infrared and NMR spectra.

Rod like colorless single crystals used in the X-ray diffraction studies were were grown in a mixture of acetone and chloroform at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to the distance N—H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93Å and the methylene C—H = 0.97 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N,N'-Bis(3-chlorophenyl)butanediamide top
Crystal data top
C16H14Cl2N2O2F(000) = 348
Mr = 337.19Dx = 1.457 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1492 reflections
a = 8.3412 (8) Åθ = 3.0–28.0°
b = 9.6501 (9) ŵ = 0.43 mm1
c = 9.5485 (9) ÅT = 293 K
β = 91.319 (9)°Rod, colourless
V = 768.39 (13) Å30.40 × 0.20 × 0.20 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.1535 independent reflections
Radiation source: fine-focus sealed tube1253 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.009
Rotation method data acquisition using ω scans.θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 104
Tmin = 0.847, Tmax = 0.919k = 1211
2574 measured reflectionsl = 1011
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.3792P]
where P = (Fo2 + 2Fc2)/3
1535 reflections(Δ/σ)max = 0.002
103 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = 0.34 e Å3
Crystal data top
C16H14Cl2N2O2V = 768.39 (13) Å3
Mr = 337.19Z = 2
Monoclinic, P21/cMo Kα radiation
a = 8.3412 (8) ŵ = 0.43 mm1
b = 9.6501 (9) ÅT = 293 K
c = 9.5485 (9) Å0.40 × 0.20 × 0.20 mm
β = 91.319 (9)°
Data collection top
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.1535 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1253 reflections with I > 2σ(I)
Tmin = 0.847, Tmax = 0.919Rint = 0.009
2574 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.25 e Å3
1535 reflectionsΔρmin = 0.34 e Å3
103 parameters
Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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) top
xyzUiso*/Ueq
Cl10.01685 (8)0.54218 (6)0.32765 (6)0.0639 (2)
O10.4067 (2)0.17690 (15)0.16810 (13)0.0521 (4)
N10.3460 (2)0.28337 (17)0.03736 (15)0.0395 (4)
H1N0.362 (3)0.279 (2)0.1207 (17)0.047*
C10.2803 (2)0.40783 (19)0.01300 (18)0.0344 (4)
C20.1918 (2)0.4127 (2)0.13434 (19)0.0382 (4)
H20.17610.33320.18730.046*
C30.1276 (2)0.5375 (2)0.1747 (2)0.0416 (5)
C40.1467 (3)0.6572 (2)0.0987 (2)0.0508 (5)
H40.10240.74040.12810.061*
C50.2335 (3)0.6502 (2)0.0223 (2)0.0520 (5)
H50.24690.72980.07570.062*
C60.3006 (2)0.5279 (2)0.0655 (2)0.0429 (5)
H60.35950.52530.14700.052*
C70.4051 (2)0.17778 (18)0.04063 (18)0.0363 (4)
C80.4738 (3)0.0598 (2)0.04393 (19)0.0481 (5)
H8A0.39340.02860.11180.058*
H8B0.56480.09380.09530.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0725 (4)0.0602 (4)0.0602 (4)0.0010 (3)0.0256 (3)0.0182 (3)
O10.0881 (12)0.0448 (8)0.0235 (7)0.0190 (8)0.0080 (6)0.0013 (6)
N10.0599 (10)0.0367 (9)0.0220 (7)0.0081 (8)0.0057 (7)0.0004 (6)
C10.0402 (9)0.0326 (9)0.0304 (9)0.0015 (8)0.0024 (7)0.0012 (7)
C20.0457 (11)0.0337 (10)0.0353 (9)0.0009 (8)0.0016 (8)0.0019 (7)
C30.0413 (10)0.0433 (11)0.0402 (10)0.0002 (9)0.0023 (8)0.0088 (8)
C40.0525 (12)0.0367 (11)0.0631 (14)0.0083 (9)0.0000 (10)0.0066 (10)
C50.0604 (13)0.0362 (11)0.0593 (13)0.0035 (10)0.0001 (10)0.0108 (10)
C60.0488 (11)0.0425 (12)0.0376 (10)0.0030 (9)0.0027 (8)0.0067 (8)
C70.0507 (11)0.0329 (9)0.0254 (8)0.0020 (8)0.0054 (7)0.0010 (7)
C80.0784 (15)0.0393 (11)0.0266 (9)0.0136 (10)0.0052 (9)0.0022 (8)
Geometric parameters (Å, º) top
Cl1—C31.747 (2)C4—C51.380 (3)
O1—C71.217 (2)C4—H40.9300
N1—C71.349 (2)C5—C61.373 (3)
N1—C11.409 (2)C5—H50.9300
N1—H1N0.811 (16)C6—H60.9300
C1—C21.389 (3)C7—C81.516 (3)
C1—C61.393 (3)C8—C8i1.487 (4)
C2—C31.377 (3)C8—H8A0.9700
C2—H20.9300C8—H8B0.9700
C3—C41.375 (3)
C7—N1—C1126.55 (15)C6—C5—C4121.3 (2)
C7—N1—H1N116.0 (16)C6—C5—H5119.4
C1—N1—H1N116.8 (16)C4—C5—H5119.4
C2—C1—C6119.64 (18)C5—C6—C1119.87 (19)
C2—C1—N1122.13 (16)C5—C6—H6120.1
C6—C1—N1118.19 (17)C1—C6—H6120.1
C3—C2—C1118.72 (18)O1—C7—N1123.58 (16)
C3—C2—H2120.6O1—C7—C8122.13 (17)
C1—C2—H2120.6N1—C7—C8114.28 (15)
C4—C3—C2122.47 (19)C8i—C8—C7113.09 (19)
C4—C3—Cl1119.31 (16)C8i—C8—H8A109.0
C2—C3—Cl1118.22 (16)C7—C8—H8A109.0
C3—C4—C5118.03 (19)C8i—C8—H8B109.0
C3—C4—H4121.0C7—C8—H8B109.0
C5—C4—H4121.0H8A—C8—H8B107.8
C7—N1—C1—C235.0 (3)C3—C4—C5—C60.7 (3)
C7—N1—C1—C6147.5 (2)C4—C5—C6—C10.5 (3)
C6—C1—C2—C30.7 (3)C2—C1—C6—C50.2 (3)
N1—C1—C2—C3178.16 (17)N1—C1—C6—C5177.74 (19)
C1—C2—C3—C40.6 (3)C1—N1—C7—O11.0 (3)
C1—C2—C3—Cl1179.87 (14)C1—N1—C7—C8177.66 (19)
C2—C3—C4—C50.1 (3)O1—C7—C8—C8i5.9 (4)
Cl1—C3—C4—C5179.44 (17)N1—C7—C8—C8i175.4 (2)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1ii0.81 (2)2.10 (2)2.8946 (19)166 (2)
Symmetry code: (ii) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H14Cl2N2O2
Mr337.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.3412 (8), 9.6501 (9), 9.5485 (9)
β (°) 91.319 (9)
V3)768.39 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.43
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.847, 0.919
No. of measured, independent and
observed [I > 2σ(I)] reflections
2574, 1535, 1253
Rint0.009
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.105, 1.07
No. of reflections1535
No. of parameters103
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.811 (16)2.103 (17)2.8946 (19)166 (2)
Symmetry code: (i) x, y+1/2, z1/2.
 

Acknowledgements

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

References

First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791–800.  CAS Google Scholar
First citationGowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106–112.  CAS Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSaraswathi, B. S., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o607.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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