N-(4-Chloro-phenyl)-N'-(4-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 symmetry at the mid-point of the central C-C bond. The dihedral angle between the benzene ring and the adjacent NH-C(O)-CH(2) 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, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules 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 = 316.78

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 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

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/S1600536811032740/ds2134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032740/ds2134Isup2.hkl

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

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) Å3	0.46 × 0.36 × 0.20 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	1452 independent reflections
Radiation source: fine-focus sealed tube	1103 reflections with I > 2σ(I)
graphite	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 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H 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 parameters	Δρmax = 0.21 e Å−3
16 restraints	Δρmin = −0.21 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	0.29114 (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)

	U11	U22	U33	U12	U13	U23
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)

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—C8i	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	C8i—C8—C7	114.7 (2)
C3—C2—H2	120.0	C8i—C8—H8A	108.6
C4—C3—C2	121.4 (2)	C7—C8—H8A	108.6
C4—C3—H3	119.3	C8i—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—C8i	−7.8 (4)
C2—C3—C4—C9	−175.4 (10)	N1—C7—C8—C8i	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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.85 (2)	2.11 (2)	2.918 (2)	160 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.11 (2)	2.918 (2)	160 (2)

Symmetry code: (i) .