N-(3-Chloro-phen-yl)-N'-(3-methyl-phen-yl)succinamide.

The asymmetric unit of the title compound, C(17)H(17)ClN(2)O(2), contains one half-mol-ecule with a center of inversion at the mid-point of the central C-C bond. The amide N-H group is anti to the meta-chloro/methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) segment is 43.5 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis. The methyl group and the Cl atom occupy the same position and were treated in a disorder model with site-occupation factors of 0.5 each.

Related literature

For our studies on the effects of substituents on the structures of N-(ar­yl)-n class="Chemical">amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2007 ▶); Saraswathi et al. (2011 ▶) and on the structures of N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶). For similar structures, see: Pierrot et al. (1984 ▶). For restrained geometry, see: Nardelli (1999 ▶).

Experimental

Crystal data

C17H17ClN2O2

M = 316.78

Triclinic,

a = 4.840 (1) Å

b = 5.560 (1) Å

c = 14.752 (3) Å

α = 93.47 (2)°

β = 91.39 (2)°

γ = 97.71 (2)°

V = 392.46 (13) Å3

Z = 1

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.44 × 0.20 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.897, T max = 0.980

2451 measured reflections

1567 independent reflections

1249 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.130

S = 0.99

1567 reflections

110 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 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/S1600536811028121/wm2508sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028121/wm2508Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028121/wm2508Isup3.cml

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

C17H17ClN2O2	Z = 1
Mr = 316.78	F(000) = 166
Triclinic, P1	Dx = 1.340 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.840 (1) Å	Cell parameters from 1094 reflections
b = 5.560 (1) Å	θ = 2.8–27.7°
c = 14.752 (3) Å	µ = 0.25 mm−1
α = 93.47 (2)°	T = 293 K
β = 91.39 (2)°	Prism, colourless
γ = 97.71 (2)°	0.44 × 0.20 × 0.08 mm
V = 392.46 (13) Å3

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	1567 independent reflections
Radiation source: fine-focus sealed tube	1249 reflections with I > 2σ(I)
graphite	Rint = 0.010
Rotation method data acquisition using ω scans	θmax = 26.3°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→5
Tmin = 0.897, Tmax = 0.980	k = −6→6
2451 measured reflections	l = −18→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.2642P] where P = (Fo2 + 2Fc2)/3
1567 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.17 e Å−3
14 restraints	Δρmin = −0.17 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)
O1	0.2418 (3)	0.7102 (3)	−0.09593 (13)	0.0651 (6)
N1	−0.2109 (3)	0.5789 (3)	−0.13211 (12)	0.0417 (5)
H1	−0.3807	0.5949	−0.1204	0.050*
C1	−0.1722 (4)	0.4107 (4)	−0.20578 (14)	0.0384 (5)
C2	0.0217 (4)	0.4712 (4)	−0.27063 (14)	0.0445 (5)
H2	0.1310	0.6226	−0.2657	0.053*
C3	0.0541 (5)	0.3084 (5)	−0.34254 (15)	0.0520 (6)
C4	−0.1059 (6)	0.0831 (5)	−0.34971 (18)	0.0630 (7)
H4A	−0.0831	−0.0283	−0.3977	0.076*
C5	−0.2988 (6)	0.0250 (5)	−0.2854 (2)	0.0659 (7)
H5A	−0.4070	−0.1269	−0.2904	0.079*
C6	−0.3364 (5)	0.1866 (4)	−0.21353 (16)	0.0502 (6)
H6	−0.4703	0.1453	−0.1709	0.060*
C7	−0.0058 (4)	0.7190 (4)	−0.08329 (14)	0.0414 (5)
C8	−0.0999 (4)	0.8842 (4)	−0.00851 (15)	0.0441 (5)
H8A	−0.1160	0.7990	0.0470	0.053*
H8B	−0.2828	0.9240	−0.0249	0.053*
C9	0.251 (3)	0.364 (4)	−0.4221 (10)	0.155 (8)	0.50
H9A	0.3567	0.5224	−0.4105	0.185*	0.50
H9B	0.1426	0.3602	−0.4776	0.185*	0.50
H9C	0.3763	0.2442	−0.4274	0.185*	0.50
Cl1	0.2883 (5)	0.3904 (5)	−0.42162 (12)	0.0742 (6)	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0252 (8)	0.0862 (13)	0.0794 (12)	0.0103 (7)	0.0031 (7)	−0.0380 (10)
N1	0.0249 (8)	0.0507 (11)	0.0484 (10)	0.0059 (7)	0.0052 (7)	−0.0101 (8)
C1	0.0295 (9)	0.0447 (12)	0.0415 (11)	0.0094 (8)	−0.0013 (8)	−0.0030 (9)
C2	0.0366 (11)	0.0497 (13)	0.0457 (12)	0.0028 (9)	0.0031 (9)	−0.0039 (9)
C3	0.0458 (12)	0.0695 (16)	0.0415 (12)	0.0152 (11)	0.0031 (10)	−0.0051 (11)
C4	0.0707 (17)	0.0637 (17)	0.0532 (14)	0.0147 (13)	0.0009 (12)	−0.0188 (12)
C5	0.0738 (18)	0.0468 (14)	0.0717 (17)	−0.0039 (12)	−0.0025 (14)	−0.0111 (12)
C6	0.0462 (12)	0.0493 (13)	0.0526 (13)	−0.0017 (10)	0.0059 (10)	−0.0003 (10)
C7	0.0283 (10)	0.0485 (12)	0.0471 (12)	0.0073 (8)	0.0046 (8)	−0.0065 (10)
C8	0.0302 (10)	0.0550 (13)	0.0458 (11)	0.0071 (9)	0.0048 (8)	−0.0114 (10)
C9	0.149 (9)	0.162 (9)	0.152 (9)	0.019 (5)	0.009 (5)	0.006 (5)
Cl1	0.0639 (9)	0.1109 (15)	0.0466 (7)	0.0093 (9)	0.0242 (7)	−0.0080 (8)

O1—C7	1.224 (2)	C4—H4A	0.9300
N1—C7	1.342 (3)	C5—C6	1.380 (3)
N1—C1	1.423 (3)	C5—H5A	0.9300
N1—H1	0.8591	C6—H6	0.9300
C1—C6	1.382 (3)	C7—C8	1.510 (3)
C1—C2	1.381 (3)	C8—C8i	1.507 (4)
C2—C3	1.378 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.379 (4)	C9—H9A	0.9600
C3—Cl1	1.686 (3)	C9—H9B	0.9600
C3—C9	1.550 (9)	C9—H9C	0.9600
C4—C5	1.369 (4)
C7—N1—C1	125.39 (16)	C6—C5—H5A	119.2
C7—N1—H1	118.5	C5—C6—C1	119.0 (2)
C1—N1—H1	116.1	C5—C6—H6	120.5
C6—C1—C2	119.8 (2)	C1—C6—H6	120.5
C6—C1—N1	119.33 (19)	O1—C7—N1	122.90 (18)
C2—C1—N1	120.85 (19)	O1—C7—C8	121.54 (18)
C3—C2—C1	120.4 (2)	N1—C7—C8	115.51 (16)
C3—C2—H2	119.8	C7—C8—C8i	112.1 (2)
C1—C2—H2	119.8	C7—C8—H8A	109.2
C2—C3—C4	120.0 (2)	C8i—C8—H8A	109.2
C2—C3—Cl1	119.1 (2)	C7—C8—H8B	109.2
C4—C3—Cl1	120.9 (2)	C8i—C8—H8B	109.2
C2—C3—C9	124.4 (7)	H8A—C8—H8B	107.9
C4—C3—C9	115.4 (7)	C3—C9—H9A	109.5
Cl1—C3—C9	5.9 (7)	C3—C9—H9B	109.5
C5—C4—C3	119.2 (2)	H9A—C9—H9B	109.5
C5—C4—H4A	120.4	C3—C9—H9C	109.5
C3—C4—H4A	120.4	H9A—C9—H9C	109.5
C4—C5—C6	121.6 (2)	H9B—C9—H9C	109.5
C4—C5—H5A	119.2
C7—N1—C1—C6	138.7 (2)	C9—C3—C4—C5	−175.8 (9)
C7—N1—C1—C2	−43.0 (3)	C3—C4—C5—C6	−0.1 (4)
C6—C1—C2—C3	−0.6 (3)	C4—C5—C6—C1	−1.0 (4)
N1—C1—C2—C3	−178.9 (2)	C2—C1—C6—C5	1.3 (3)
C1—C2—C3—C4	−0.5 (4)	N1—C1—C6—C5	179.6 (2)
C1—C2—C3—Cl1	178.8 (2)	C1—N1—C7—O1	−2.4 (4)
C1—C2—C3—C9	175.8 (9)	C1—N1—C7—C8	179.8 (2)
C2—C3—C4—C5	0.8 (4)	O1—C7—C8—C8i	32.9 (4)
Cl1—C3—C4—C5	−178.4 (2)	N1—C7—C8—C8i	−149.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ii	0.86	2.05	2.894 (2)	168.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.05	2.894 (2)	168

Symmetry code: (i) .