N-(2-Chloro-phen-yl)-N'-(2-methyl-phen-yl)succinamide.

In the title compound, C(17)H(17)ClN(2)O(2), the asymmetric unit contains half a mol-ecule with a centre of symmetry at the mid-point of the central C-C bond. The conformations of the amide O atoms are anti to the methyl-ene atoms. Further, the N-H bonds in the amide fragments are anti to the ortho-chloro/methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) segment in the two halves of the mol-ecule is 62.0 (2)°. In the crystal, a series of N-H⋯O inter-molecular hydrogen bonds link the mol-ecules into column-like infinite chains along the a axis. The methyl and Cl groups are disordered with respect to the ortho positions of the benzene ring, with site-occupation factors of 0.5 each.

Related literature

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

Experimental

Crystal data

C17H17ClN2O2

M = 316.78

Monoclinic,

a = 11.541 (3) Å

b = 7.908 (2) Å

c = 8.798 (2) Å

β = 102.55 (2)°

V = 783.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.48 × 0.04 × 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 = 0.889, T max = 0.990

2598 measured reflections

1391 independent reflections

824 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.105

wR(F 2) = 0.164

S = 1.28

1391 reflections

112 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.31 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035616/vm2112sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035616/vm2112Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035616/vm2112Isup3.cml

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

C17H17ClN2O2	F(000) = 332
Mr = 316.78	Dx = 1.342 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 611 reflections
a = 11.541 (3) Å	θ = 2.6–27.9°
b = 7.908 (2) Å	µ = 0.25 mm−1
c = 8.798 (2) Å	T = 293 K
β = 102.55 (2)°	Needle, colourless
V = 783.8 (3) Å3	0.48 × 0.04 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1391 independent reflections
Radiation source: fine-focus sealed tube	824 reflections with I > 2σ(I)
graphite	Rint = 0.044
Rotation method data acquisition using ω scans	θmax = 25.2°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→13
Tmin = 0.889, Tmax = 0.990	k = −9→5
2598 measured reflections	l = −9→10

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)] = 0.105	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.28	w = 1/[σ2(Fo2) + (0.0062P)2 + 2.1127P] where P = (Fo2 + 2Fc2)/3
1391 reflections	(Δ/σ)max < 0.001
112 parameters	Δρmax = 0.26 e Å−3
9 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2685 (5)	0.4153 (7)	0.0447 (6)	0.0318 (14)
C2	0.1709 (5)	0.3763 (7)	0.1055 (6)	0.0370 (15)
C3	0.1179 (6)	0.5036 (9)	0.1745 (7)	0.0526 (18)
H3	0.0527	0.4781	0.2165	0.063*
C4	0.1595 (6)	0.6660 (9)	0.1821 (8)	0.0579 (19)
H4	0.1227	0.7495	0.2293	0.069*
C5	0.2556 (6)	0.7058 (8)	0.1202 (8)	0.0557 (19)
H5	0.2839	0.8163	0.1248	0.067*
C6	0.3099 (6)	0.5805 (8)	0.0512 (7)	0.0489 (18)
H6	0.3747	0.6071	0.0087	0.059*
C7	0.3869 (5)	0.1569 (7)	0.0508 (6)	0.0303 (13)
C8	0.4477 (5)	0.0460 (7)	−0.0481 (6)	0.0353 (14)
H8A	0.3913	−0.0357	−0.1034	0.042*
H8B	0.4743	0.1154	−0.1249	0.042*
C9	0.110 (3)	0.203 (3)	0.095 (5)	0.057 (12)	0.50
H9A	0.1531	0.1238	0.0459	0.068*	0.50
H9B	0.0301	0.2127	0.0350	0.068*	0.50
H9C	0.1083	0.1639	0.1980	0.068*	0.50
N1	0.3288 (4)	0.2897 (6)	−0.0256 (5)	0.0346 (12)
H1N	0.338 (4)	0.316 (7)	−0.116 (3)	0.041*
O1	0.3888 (3)	0.1237 (5)	0.1871 (4)	0.0410 (11)
Cl1	0.1161 (9)	0.1725 (10)	0.0927 (15)	0.057 (2)	0.50

	U11	U22	U33	U12	U13	U23
C1	0.038 (3)	0.033 (3)	0.026 (3)	0.007 (3)	0.011 (3)	0.005 (3)
C2	0.039 (4)	0.037 (4)	0.037 (4)	0.006 (3)	0.012 (3)	0.002 (3)
C3	0.052 (4)	0.062 (5)	0.050 (4)	0.021 (4)	0.025 (3)	0.002 (4)
C4	0.070 (5)	0.046 (5)	0.061 (5)	0.027 (4)	0.021 (4)	−0.005 (4)
C5	0.075 (5)	0.028 (4)	0.065 (5)	0.009 (4)	0.018 (4)	0.003 (3)
C6	0.063 (5)	0.038 (4)	0.052 (4)	0.003 (3)	0.027 (4)	0.011 (3)
C7	0.039 (3)	0.029 (3)	0.024 (3)	0.000 (3)	0.009 (3)	−0.002 (3)
C8	0.044 (4)	0.039 (3)	0.026 (3)	0.010 (3)	0.013 (3)	−0.006 (3)
C9	0.063 (15)	0.051 (13)	0.057 (14)	0.014 (8)	0.016 (9)	−0.003 (8)
N1	0.048 (3)	0.037 (3)	0.025 (3)	0.010 (2)	0.023 (2)	0.004 (2)
O1	0.065 (3)	0.041 (2)	0.023 (2)	0.017 (2)	0.021 (2)	0.0045 (19)
Cl1	0.046 (3)	0.051 (3)	0.084 (5)	−0.010 (3)	0.031 (3)	−0.008 (3)

C1—C2	1.383 (7)	C6—H6	0.9300
C1—C6	1.388 (7)	C7—O1	1.223 (6)
C1—N1	1.429 (6)	C7—N1	1.345 (7)
C2—C3	1.384 (7)	C7—C8	1.512 (7)
C2—C9	1.535 (10)	C8—C8i	1.503 (10)
C2—Cl1	1.725 (7)	C8—H8A	0.9700
C3—C4	1.367 (9)	C8—H8B	0.9700
C3—H3	0.9300	C9—H9A	0.9600
C4—C5	1.375 (8)	C9—H9B	0.9600
C4—H4	0.9300	C9—H9C	0.9600
C5—C6	1.382 (8)	N1—H1N	0.853 (19)
C5—H5	0.9300
C2—C1—C6	119.7 (5)	C1—C6—H6	119.7
C2—C1—N1	121.8 (5)	O1—C7—N1	124.0 (5)
C6—C1—N1	118.5 (5)	O1—C7—C8	121.9 (5)
C1—C2—C3	118.8 (5)	N1—C7—C8	114.1 (4)
C1—C2—C9	125.3 (16)	C8i—C8—C7	111.9 (5)
C3—C2—C9	115.8 (15)	C8i—C8—H8A	109.2
C1—C2—Cl1	120.0 (5)	C7—C8—H8A	109.2
C3—C2—Cl1	121.2 (6)	C8i—C8—H8B	109.2
C9—C2—Cl1	5.9 (18)	C7—C8—H8B	109.2
C4—C3—C2	121.4 (6)	H8A—C8—H8B	107.9
C4—C3—H3	119.3	C2—C9—H9A	109.5
C2—C3—H3	119.3	C2—C9—H9B	109.5
C3—C4—C5	120.0 (6)	H9A—C9—H9B	109.5
C3—C4—H4	120.0	C2—C9—H9C	109.5
C5—C4—H4	120.0	H9A—C9—H9C	109.5
C4—C5—C6	119.5 (6)	H9B—C9—H9C	109.5
C4—C5—H5	120.3	C7—N1—C1	124.3 (4)
C6—C5—H5	120.3	C7—N1—H1N	121 (4)
C5—C6—C1	120.5 (5)	C1—N1—H1N	114 (4)
C5—C6—H6	119.7
C6—C1—C2—C3	−1.2 (9)	C3—C4—C5—C6	−0.3 (11)
N1—C1—C2—C3	178.9 (5)	C4—C5—C6—C1	−0.3 (10)
C6—C1—C2—C9	175 (2)	C2—C1—C6—C5	1.1 (9)
N1—C1—C2—C9	−5(2)	N1—C1—C6—C5	−179.0 (6)
C6—C1—C2—Cl1	178.0 (7)	O1—C7—C8—C8i	−28.1 (9)
N1—C1—C2—Cl1	−1.9 (9)	N1—C7—C8—C8i	153.7 (6)
C1—C2—C3—C4	0.6 (10)	O1—C7—N1—C1	4.3 (9)
C9—C2—C3—C4	−176 (2)	C8—C7—N1—C1	−177.6 (5)
Cl1—C2—C3—C4	−178.7 (7)	C2—C1—N1—C7	−64.2 (8)
C2—C3—C4—C5	0.2 (11)	C6—C1—N1—C7	115.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.85 (2)	2.00 (2)	2.846 (5)	170 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.00 (2)	2.846 (5)	170 (5)

Symmetry code: (i) .