organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-(4-Chloro­phenyl)-N′-(4-methyl­phen­yl)succinamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 5 August 2011; accepted 12 August 2011; online 27 August 2011)

The asymmetric unit of the title compound, C17H17ClN2O2, contains one half-mol­ecule with a center of symmetry at the mid-point of the central C—C bond. The dihedral angle between the benzene ring and the adjacent NH—C(O)—CH2 group is 39.9 (1)°. The methyl and Cl groups are disordered with respect to the para-positions of the benzene ring, with site-occupation factors of 0.5 each. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into chains parallel to the baxis.

Related literature

For our studies on the effects of substituents on the structures of N-(ar­yl)-amides, see: Arjunan et al. (2004[Arjunan, V., Mohan, S., Subramanian, S. & Gowda, B. T. (2004). Spectrochim. Acta Part A, 60, 1141-1159.]); Bhat & Gowda (2000[Bhat, D. K. & Gowda, B. T. (2000). J. Indian Chem. Soc. 77, 279-284.]); Saraswathi et al. (2011[Saraswathi, B. S., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2077.]), on N-(ar­yl)-methane­sulfon­amides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.]) and on aryl­sulfonamides, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Kožíšek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.]). For a similar structure, see Pierrot et al. (1984[Pierrot, M., Baldy, A., Maire, J. C., Mehrotra, R. C., Kapoor, T. S. & Bachlas, B. P. (1984). Acta Cryst. C40, 1931-1934.]). For restrained geometry, see: Nardelli (1999[Nardelli, M. (1999). J. Appl. Cryst. 32, 563-571.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17ClN2O2

  • Mr = 316.78

  • Monoclinic, P 21 /c

  • a = 17.305 (3) Å

  • b = 4.8446 (6) Å

  • c = 9.726 (1) Å

  • β = 101.58 (2)°

  • V = 798.79 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 293 K

  • 0.46 × 0.36 × 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 = 0.895, Tmax = 0.952

  • 2538 measured reflections

  • 1452 independent reflections

  • 1103 reflections with I > 2σ(I)

  • Rint = 0.009

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.131

  • S = 1.03

  • 1452 reflections

  • 112 parameters

  • 16 restraints

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.85 (2) 2.11 (2) 2.918 (2) 160 (2)
Symmetry code: (i) x, y+1, z.

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 part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Bhat & Gowda, 2000; Saraswathi et al., 2011), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and arylsulfonamides(Gowda et al., 2003), in the present work, the structure of N-(4-Chlorophenyl),N-(4-methylphenyl)-succinamide (I) has been determined (Fig.1). The asymmetric unit of (I) contains half a molecule with a center of symmetry at the mid-point of the central C—C bond, similar to that obseved in bis(2-chlorophenylaminocarbonylmethyl)disulfide (II)(Pierrot et al., 1984), N-(3-Chlorophenyl),N-(3-methylphenyl)- succinamide (III) (Saraswathi et al., 2011)

The conformations of the amide O atoms are anti to the H atoms attached to the adjacent C atoms.

The dihedral angle between the benzene ring and the NH—C(O)—CH2 segment in the two halves of the molecule is 39.9 (1)°, compared to the value of 43.5 (1)° in (III).

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 studies on the effects of substituents on the structures of N-(aryl)-amides, see: Arjunan et al. (2004); Bhat & Gowda (2000); Saraswathi et al. (2011), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on arylsulfonamides, see: Gowda et al. (2003). For similar structures, see Pierrot et al. (1984). For restrained geometry, see: Nardelli (1999).

Experimental top

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with 4-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 4-chloroaniline. The resultant solid N-(4-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-(4-chlorophenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of 4-methylaniline 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-(4-chlorophenyl), N-(4-methylphenyl)-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 toluene (3:1 v/v). The compound was characterized by its infrared and NMR spectra.

Rod like colorless single crystals used in X-ray diffraction studies were grown in a mixture of acetone and toluene (3:1 v/v) 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 = 0.93 Å, methyl C—H = 0.97 Å, and the methylene C—H = 0.97 Å.

All H atoms were refined with isotropic displacement parameters. The Uiso(H) values were set at 1.2Ueq(C-aromatic, N) and 1.5Ueq(C-methyl).

C9 and CL1 are disordered and were refined using a split model. The corresponding site-occupation factors were fixed to 0.50:0.50. The bond lenghts C4–C9 were restrained to 1.54 (1) Å and C4–CL1 to 1.74 (1) Å, respectivily. The Uij components of these atoms were restrained to approximate isotropic behavoir (Nardelli, 1999).

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 the title compound, showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level. symmetry code: (i) -x + 1, -y, -z + 1.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(4-Chlorophenyl)-N'-(4-methylphenyl)succinamide top
Crystal data top
C17H17ClN2O2F(000) = 332
Mr = 316.78Dx = 1.317 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1260 reflections
a = 17.305 (3) Åθ = 2.7–27.6°
b = 4.8446 (6) ŵ = 0.25 mm1
c = 9.726 (1) ÅT = 293 K
β = 101.58 (2)°Rod, colourless
V = 798.79 (19) Å30.46 × 0.36 × 0.20 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
1452 independent reflections
Radiation source: fine-focus sealed tube1103 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.009
Rotation method data acquisition using ω scans.θmax = 25.4°, θmin = 3.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1520
Tmin = 0.895, Tmax = 0.952k = 45
2538 measured reflectionsl = 1111
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0576P)2 + 0.3157P]
where P = (Fo2 + 2Fc2)/3
1452 reflections(Δ/σ)max < 0.001
112 parametersΔρmax = 0.21 e Å3
16 restraintsΔρmin = 0.21 e Å3
Crystal data top
C17H17ClN2O2V = 798.79 (19) Å3
Mr = 316.78Z = 2
Monoclinic, P21/cMo Kα radiation
a = 17.305 (3) ŵ = 0.25 mm1
b = 4.8446 (6) ÅT = 293 K
c = 9.726 (1) Å0.46 × 0.36 × 0.20 mm
β = 101.58 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
1452 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1103 reflections with I > 2σ(I)
Tmin = 0.895, Tmax = 0.952Rint = 0.009
2538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04816 restraints
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.21 e Å3
1452 reflectionsΔρmin = 0.21 e Å3
112 parameters
Special details top

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*/UeqOcc. (<1)
C10.29114 (11)0.0736 (4)0.17026 (19)0.0472 (5)
C20.29237 (13)0.1283 (5)0.0720 (2)0.0635 (6)
H20.33900.22180.06960.076*
C30.22412 (15)0.1929 (6)0.0237 (2)0.0764 (7)
H30.22550.33120.08950.092*
C40.15544 (13)0.0589 (6)0.0236 (2)0.0711 (6)
C50.15403 (14)0.1444 (6)0.0728 (3)0.0846 (8)
H50.10740.23910.07350.102*
C60.22151 (15)0.2106 (5)0.1694 (3)0.0750 (7)
H60.21980.34960.23470.090*
C70.41174 (11)0.0321 (4)0.34385 (18)0.0468 (5)
C80.47503 (13)0.0983 (4)0.4538 (2)0.0634 (6)
H8A0.50840.21070.40710.076*
H8B0.45010.22020.51100.076*
C90.0768 (8)0.134 (5)0.1191 (19)0.169 (10)0.50
H9A0.06660.32710.11010.203*0.50
H9B0.07920.09300.21480.203*0.50
H9C0.03520.02830.09240.203*0.50
Cl10.07114 (18)0.1382 (10)0.1455 (5)0.1135 (11)0.50
N10.35940 (10)0.1458 (3)0.27126 (17)0.0535 (5)
H1N0.3632 (13)0.315 (3)0.294 (2)0.064*
O10.40838 (9)0.2812 (3)0.32397 (15)0.0642 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0506 (11)0.0398 (10)0.0471 (10)0.0047 (9)0.0000 (8)0.0038 (8)
C20.0569 (12)0.0745 (15)0.0547 (12)0.0060 (11)0.0009 (10)0.0138 (11)
C30.0749 (17)0.0884 (18)0.0576 (13)0.0052 (14)0.0061 (11)0.0202 (12)
C40.0550 (13)0.0906 (16)0.0607 (13)0.0145 (13)0.0048 (10)0.0112 (10)
C50.0548 (14)0.104 (2)0.0894 (17)0.0146 (14)0.0000 (13)0.0008 (13)
C60.0700 (15)0.0706 (15)0.0775 (16)0.0144 (13)0.0018 (12)0.0158 (12)
C70.0537 (11)0.0347 (10)0.0483 (10)0.0079 (8)0.0011 (8)0.0012 (8)
C80.0693 (14)0.0389 (11)0.0692 (13)0.0098 (10)0.0173 (11)0.0008 (9)
C90.119 (11)0.237 (18)0.120 (12)0.019 (11)0.051 (7)0.022 (10)
Cl10.0731 (14)0.155 (3)0.0934 (14)0.0297 (16)0.0288 (11)0.0018 (14)
N10.0601 (10)0.0317 (8)0.0599 (10)0.0019 (7)0.0090 (8)0.0033 (7)
O10.0761 (11)0.0309 (7)0.0738 (10)0.0050 (6)0.0134 (8)0.0028 (6)
Geometric parameters (Å, º) top
C1—C21.371 (3)C6—H60.9300
C1—C61.374 (3)C7—O11.222 (2)
C1—N11.420 (2)C7—N11.344 (2)
C2—C31.385 (3)C7—C81.507 (3)
C2—H20.9300C8—C8i1.466 (4)
C3—C41.354 (3)C8—H8A0.9700
C3—H30.9300C8—H8B0.9700
C4—C51.363 (4)C9—H9A0.9600
C4—C91.529 (9)C9—H9B0.9600
C4—Cl11.728 (4)C9—H9C0.9600
C5—C61.382 (3)N1—H1N0.847 (15)
C5—H50.9300
C2—C1—C6118.5 (2)C5—C6—H6119.6
C2—C1—N1122.07 (18)O1—C7—N1123.02 (17)
C6—C1—N1119.45 (18)O1—C7—C8122.08 (17)
C1—C2—C3120.0 (2)N1—C7—C8114.89 (16)
C1—C2—H2120.0C8i—C8—C7114.7 (2)
C3—C2—H2120.0C8i—C8—H8A108.6
C4—C3—C2121.4 (2)C7—C8—H8A108.6
C4—C3—H3119.3C8i—C8—H8B108.6
C2—C3—H3119.3C7—C8—H8B108.6
C3—C4—C5118.9 (2)H8A—C8—H8B107.6
C3—C4—C9124.0 (9)C4—C9—H9A109.5
C5—C4—C9116.9 (9)C4—C9—H9B109.5
C3—C4—Cl1120.9 (3)H9A—C9—H9B109.5
C5—C4—Cl1120.2 (3)C4—C9—H9C109.5
C9—C4—Cl15.7 (9)H9A—C9—H9C109.5
C4—C5—C6120.4 (2)H9B—C9—H9C109.5
C4—C5—H5119.8C7—N1—C1125.78 (16)
C6—C5—H5119.8C7—N1—H1N118.4 (15)
C1—C6—C5120.8 (2)C1—N1—H1N115.3 (15)
C1—C6—H6119.6
C6—C1—C2—C31.0 (3)C2—C1—C6—C50.7 (4)
N1—C1—C2—C3179.5 (2)N1—C1—C6—C5179.8 (2)
C1—C2—C3—C40.5 (4)C4—C5—C6—C10.1 (4)
C2—C3—C4—C50.3 (4)O1—C7—C8—C8i7.8 (4)
C2—C3—C4—C9175.4 (10)N1—C7—C8—C8i171.6 (3)
C2—C3—C4—Cl1179.0 (3)O1—C7—N1—C14.5 (3)
C3—C4—C5—C60.5 (4)C8—C7—N1—C1174.84 (18)
C9—C4—C5—C6175.4 (9)C2—C1—N1—C742.7 (3)
Cl1—C4—C5—C6179.3 (3)C6—C1—N1—C7137.8 (2)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1ii0.85 (2)2.11 (2)2.918 (2)160 (2)
Symmetry code: (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H17ClN2O2
Mr316.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)17.305 (3), 4.8446 (6), 9.726 (1)
β (°) 101.58 (2)
V3)798.79 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.46 × 0.36 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.895, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
2538, 1452, 1103
Rint0.009
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.131, 1.03
No. of reflections1452
No. of parameters112
No. of restraints16
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (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···O1i0.847 (15)2.105 (17)2.918 (2)160 (2)
Symmetry code: (i) x, y+1, z.
 

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 citationArjunan, V., Mohan, S., Subramanian, S. & Gowda, B. T. (2004). Spectrochim. Acta Part A, 60, 1141–1159.  CrossRef CAS Google Scholar
First citationBhat, D. K. & Gowda, B. T. (2000). J. Indian Chem. Soc. 77, 279–284.  CAS Google Scholar
First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Jyothi, K., Kožíšek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656–660.  CAS Google Scholar
First citationNardelli, M. (1999). J. Appl. Cryst. 32, 563–571.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationPierrot, M., Baldy, A., Maire, J. C., Mehrotra, R. C., Kapoor, T. S. & Bachlas, B. P. (1984). Acta Cryst. C40, 1931–1934.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSaraswathi, B. S., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2077.  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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