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

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); 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 a similar structure, see Pierrot et al. (1984). For restrained geometry, see: Nardelli (1999).

Experimental

Crystal data

• C₁₇H₁₇ClN₂O₂

• M_r = 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) ų

• 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) T_min = 0.895, T_max = 0.952

• 2538 measured reflections

• 1452 independent reflections

• 1103 reflections with I > 2σ(I)

• R_int = 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

• Δρ_max = 0.21 e Å⁻³

• Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1^i	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); 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.

Supporting information

S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

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 U_iso(H) values were set at 1.2U_eq(C-aromatic, N) and 1.5U_eq(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 U^ij components of these atoms were restrained to approximate isotropic behavoir (Nardelli, 1999).

Computing details

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

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

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

Crystal data

C17H17ClN2O2	F(000) = 332
Mr = 316.78	Dx = 1.317 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1260 reflections
a = 17.305 (3) Å	θ = 2.7–27.6°
b = 4.8446 (6) Å	µ = 0.25 mm^−1
c = 9.726 (1) Å	T = 293 K
β = 101.58 (2)°	Rod, colourless
V = 798.79 (19) Å^3	0.46 × 0.36 × 0.20 mm
Z = 2

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	1452 independent reflections
Radiation source: fine-focus sealed tube	1103 reflections with I > 2σ(I)
Graphite monochromator	Rint = 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 = −15→20
Tmin = 0.895, Tmax = 0.952	k = −4→5
2538 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0576P)^2 + 0.3157P] where P = (Fo^2 + 2Fc^2)/3
1452 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.21 e Å^−3
16 restraints	Δρmin = −0.21 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.29114 (11)	0.0736 (4)	0.17026 (19)	0.0472 (5)
C2	0.29237 (13)	−0.1283 (5)	0.0720 (2)	0.0635 (6)
H2	0.3390	−0.2218	0.0696	0.076*
C3	0.22412 (15)	−0.1929 (6)	−0.0237 (2)	0.0764 (7)
H3	0.2255	−0.3312	−0.0895	0.092*
C4	0.15544 (13)	−0.0589 (6)	−0.0236 (2)	0.0711 (6)
C5	0.15403 (14)	0.1444 (6)	0.0728 (3)	0.0846 (8)
H5	0.1074	0.2391	0.0735	0.102*
C6	0.22151 (15)	0.2106 (5)	0.1694 (3)	0.0750 (7)
H6	0.2198	0.3496	0.2347	0.090*
C7	0.41174 (11)	−0.0321 (4)	0.34385 (18)	0.0468 (5)
C8	0.47503 (13)	0.0983 (4)	0.4538 (2)	0.0634 (6)
H8A	0.5084	0.2107	0.4071	0.076*
H8B	0.4501	0.2202	0.5110	0.076*
C9	0.0768 (8)	−0.134 (5)	−0.1191 (19)	0.169 (10)	0.50
H9A	0.0666	−0.3271	−0.1101	0.203*	0.50
H9B	0.0792	−0.0930	−0.2148	0.203*	0.50
H9C	0.0352	−0.0283	−0.0924	0.203*	0.50
Cl1	0.07114 (18)	−0.1382 (10)	−0.1455 (5)	0.1135 (11)	0.50
N1	0.35940 (10)	0.1458 (3)	0.27126 (17)	0.0535 (5)
H1N	0.3632 (13)	0.315 (3)	0.294 (2)	0.064*
O1	0.40838 (9)	−0.2812 (3)	0.32397 (15)	0.0642 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0506 (11)	0.0398 (10)	0.0471 (10)	−0.0047 (9)	0.0000 (8)	0.0038 (8)
C2	0.0569 (12)	0.0745 (15)	0.0547 (12)	0.0060 (11)	0.0009 (10)	−0.0138 (11)
C3	0.0749 (17)	0.0884 (18)	0.0576 (13)	−0.0052 (14)	−0.0061 (11)	−0.0202 (12)
C4	0.0550 (13)	0.0906 (16)	0.0607 (13)	−0.0145 (13)	−0.0048 (10)	0.0112 (10)
C5	0.0548 (14)	0.104 (2)	0.0894 (17)	0.0146 (14)	0.0000 (13)	−0.0008 (13)
C6	0.0700 (15)	0.0706 (15)	0.0775 (16)	0.0144 (13)	−0.0018 (12)	−0.0158 (12)
C7	0.0537 (11)	0.0347 (10)	0.0483 (10)	−0.0079 (8)	0.0011 (8)	0.0012 (8)
C8	0.0693 (14)	0.0389 (11)	0.0692 (13)	−0.0098 (10)	−0.0173 (11)	0.0008 (9)
C9	0.119 (11)	0.237 (18)	0.120 (12)	−0.019 (11)	−0.051 (7)	−0.022 (10)
Cl1	0.0731 (14)	0.155 (3)	0.0934 (14)	−0.0297 (16)	−0.0288 (11)	−0.0018 (14)
N1	0.0601 (10)	0.0317 (8)	0.0599 (10)	−0.0019 (7)	−0.0090 (8)	−0.0033 (7)
O1	0.0761 (11)	0.0309 (7)	0.0738 (10)	−0.0050 (6)	−0.0134 (8)	−0.0028 (6)

Geometric parameters (Å, º)

C1—C2	1.371 (3)	C6—H6	0.9300
C1—C6	1.374 (3)	C7—O1	1.222 (2)
C1—N1	1.420 (2)	C7—N1	1.344 (2)
C2—C3	1.385 (3)	C7—C8	1.507 (3)
C2—H2	0.9300	C8—C8^i	1.466 (4)
C3—C4	1.354 (3)	C8—H8A	0.9700
C3—H3	0.9300	C8—H8B	0.9700
C4—C5	1.363 (4)	C9—H9A	0.9600
C4—C9	1.529 (9)	C9—H9B	0.9600
C4—Cl1	1.728 (4)	C9—H9C	0.9600
C5—C6	1.382 (3)	N1—H1N	0.847 (15)
C5—H5	0.9300
C2—C1—C6	118.5 (2)	C5—C6—H6	119.6
C2—C1—N1	122.07 (18)	O1—C7—N1	123.02 (17)
C6—C1—N1	119.45 (18)	O1—C7—C8	122.08 (17)
C1—C2—C3	120.0 (2)	N1—C7—C8	114.89 (16)
C1—C2—H2	120.0	C8^i—C8—C7	114.7 (2)
C3—C2—H2	120.0	C8^i—C8—H8A	108.6
C4—C3—C2	121.4 (2)	C7—C8—H8A	108.6
C4—C3—H3	119.3	C8^i—C8—H8B	108.6
C2—C3—H3	119.3	C7—C8—H8B	108.6
C3—C4—C5	118.9 (2)	H8A—C8—H8B	107.6
C3—C4—C9	124.0 (9)	C4—C9—H9A	109.5
C5—C4—C9	116.9 (9)	C4—C9—H9B	109.5
C3—C4—Cl1	120.9 (3)	H9A—C9—H9B	109.5
C5—C4—Cl1	120.2 (3)	C4—C9—H9C	109.5
C9—C4—Cl1	5.7 (9)	H9A—C9—H9C	109.5
C4—C5—C6	120.4 (2)	H9B—C9—H9C	109.5
C4—C5—H5	119.8	C7—N1—C1	125.78 (16)
C6—C5—H5	119.8	C7—N1—H1N	118.4 (15)
C1—C6—C5	120.8 (2)	C1—N1—H1N	115.3 (15)
C1—C6—H6	119.6
C6—C1—C2—C3	−1.0 (3)	C2—C1—C6—C5	0.7 (4)
N1—C1—C2—C3	179.5 (2)	N1—C1—C6—C5	−179.8 (2)
C1—C2—C3—C4	0.5 (4)	C4—C5—C6—C1	0.1 (4)
C2—C3—C4—C5	0.3 (4)	O1—C7—C8—C8^i	−7.8 (4)
C2—C3—C4—C9	−175.4 (10)	N1—C7—C8—C8^i	171.6 (3)
C2—C3—C4—Cl1	179.0 (3)	O1—C7—N1—C1	4.5 (3)
C3—C4—C5—C6	−0.5 (4)	C8—C7—N1—C1	−174.84 (18)
C9—C4—C5—C6	175.4 (9)	C2—C1—N1—C7	−42.7 (3)
Cl1—C4—C5—C6	−179.3 (3)	C6—C1—N1—C7	137.8 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^ii	0.85 (2)	2.11 (2)	2.918 (2)	160 (2)

Symmetry code: (ii) x, y+1, z.