N,N'-Bis(3-chloro-phen-yl)succinamide.

The complete molecule of the title compound, C(16)H(14)Cl(2)N(2)O(2), is generated by crystallographic inversion symmetry. The dihedral angle between the benzene ring and the NH-C(O)-C fragment is 32.8 (1)°. In the crystal, the molecules are linked by N-H⋯O hydrogen bonds into [100] chains.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶); Saraswathi et al. (2011 ▶), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and of N-(substitutedphen­yl)-p-substituted-benzene­sulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C16H14Cl2N2O2

M = 337.19

Monoclinic,

a = 8.3412 (8) Å

b = 9.6501 (9) Å

c = 9.5485 (9) Å

β = 91.319 (9)°

V = 768.39 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.847, T max = 0.919

2574 measured reflections

1535 independent reflections

1253 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.07

1535 reflections

103 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.34 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 datablocks I, global. DOI: 10.1107/S1600536811010440/ds2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010440/ds2100Isup2.hkl

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

C16H14Cl2N2O2	F(000) = 348
Mr = 337.19	Dx = 1.457 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1492 reflections
a = 8.3412 (8) Å	θ = 3.0–28.0°
b = 9.6501 (9) Å	µ = 0.43 mm−1
c = 9.5485 (9) Å	T = 293 K
β = 91.319 (9)°	Rod, colourless
V = 768.39 (13) Å3	0.40 × 0.20 × 0.20 mm
Z = 2

Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.	1535 independent reflections
Radiation source: fine-focus sealed tube	1253 reflections with I > 2σ(I)
graphite	Rint = 0.009
Rotation method data acquisition using ω scans.	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→4
Tmin = 0.847, Tmax = 0.919	k = −12→11
2574 measured reflections	l = −10→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.3792P] where P = (Fo2 + 2Fc2)/3
1535 reflections	(Δ/σ)max = 0.002
103 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.34 e Å−3

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.01685 (8)	0.54218 (6)	0.32765 (6)	0.0639 (2)
O1	0.4067 (2)	0.17690 (15)	0.16810 (13)	0.0521 (4)
N1	0.3460 (2)	0.28337 (17)	−0.03736 (15)	0.0395 (4)
H1N	0.362 (3)	0.279 (2)	−0.1207 (17)	0.047*
C1	0.2803 (2)	0.40783 (19)	0.01300 (18)	0.0344 (4)
C2	0.1918 (2)	0.4127 (2)	0.13434 (19)	0.0382 (4)
H2	0.1761	0.3332	0.1873	0.046*
C3	0.1276 (2)	0.5375 (2)	0.1747 (2)	0.0416 (5)
C4	0.1467 (3)	0.6572 (2)	0.0987 (2)	0.0508 (5)
H4	0.1024	0.7404	0.1281	0.061*
C5	0.2335 (3)	0.6502 (2)	−0.0223 (2)	0.0520 (5)
H5	0.2469	0.7298	−0.0757	0.062*
C6	0.3006 (2)	0.5279 (2)	−0.0655 (2)	0.0429 (5)
H6	0.3595	0.5253	−0.1470	0.052*
C7	0.4051 (2)	0.17778 (18)	0.04063 (18)	0.0363 (4)
C8	0.4738 (3)	0.0598 (2)	−0.04393 (19)	0.0481 (5)
H8A	0.3934	0.0286	−0.1118	0.058*
H8B	0.5648	0.0938	−0.0953	0.058*

	U11	U22	U33	U12	U13	U23
Cl1	0.0725 (4)	0.0602 (4)	0.0602 (4)	0.0010 (3)	0.0256 (3)	−0.0182 (3)
O1	0.0881 (12)	0.0448 (8)	0.0235 (7)	0.0190 (8)	0.0080 (6)	0.0013 (6)
N1	0.0599 (10)	0.0367 (9)	0.0220 (7)	0.0081 (8)	0.0057 (7)	0.0004 (6)
C1	0.0402 (9)	0.0326 (9)	0.0304 (9)	0.0015 (8)	−0.0024 (7)	−0.0012 (7)
C2	0.0457 (11)	0.0337 (10)	0.0353 (9)	−0.0009 (8)	0.0016 (8)	−0.0019 (7)
C3	0.0413 (10)	0.0433 (11)	0.0402 (10)	0.0002 (9)	0.0023 (8)	−0.0088 (8)
C4	0.0525 (12)	0.0367 (11)	0.0631 (14)	0.0083 (9)	0.0000 (10)	−0.0066 (10)
C5	0.0604 (13)	0.0362 (11)	0.0593 (13)	0.0035 (10)	−0.0001 (10)	0.0108 (10)
C6	0.0488 (11)	0.0425 (12)	0.0376 (10)	0.0030 (9)	0.0027 (8)	0.0067 (8)
C7	0.0507 (11)	0.0329 (9)	0.0254 (8)	0.0020 (8)	0.0054 (7)	−0.0010 (7)
C8	0.0784 (15)	0.0393 (11)	0.0266 (9)	0.0136 (10)	0.0052 (9)	−0.0022 (8)

Cl1—C3	1.747 (2)	C4—C5	1.380 (3)
O1—C7	1.217 (2)	C4—H4	0.9300
N1—C7	1.349 (2)	C5—C6	1.373 (3)
N1—C1	1.409 (2)	C5—H5	0.9300
N1—H1N	0.811 (16)	C6—H6	0.9300
C1—C2	1.389 (3)	C7—C8	1.516 (3)
C1—C6	1.393 (3)	C8—C8i	1.487 (4)
C2—C3	1.377 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.375 (3)
C7—N1—C1	126.55 (15)	C6—C5—C4	121.3 (2)
C7—N1—H1N	116.0 (16)	C6—C5—H5	119.4
C1—N1—H1N	116.8 (16)	C4—C5—H5	119.4
C2—C1—C6	119.64 (18)	C5—C6—C1	119.87 (19)
C2—C1—N1	122.13 (16)	C5—C6—H6	120.1
C6—C1—N1	118.19 (17)	C1—C6—H6	120.1
C3—C2—C1	118.72 (18)	O1—C7—N1	123.58 (16)
C3—C2—H2	120.6	O1—C7—C8	122.13 (17)
C1—C2—H2	120.6	N1—C7—C8	114.28 (15)
C4—C3—C2	122.47 (19)	C8i—C8—C7	113.09 (19)
C4—C3—Cl1	119.31 (16)	C8i—C8—H8A	109.0
C2—C3—Cl1	118.22 (16)	C7—C8—H8A	109.0
C3—C4—C5	118.03 (19)	C8i—C8—H8B	109.0
C3—C4—H4	121.0	C7—C8—H8B	109.0
C5—C4—H4	121.0	H8A—C8—H8B	107.8
C7—N1—C1—C2	−35.0 (3)	C3—C4—C5—C6	−0.7 (3)
C7—N1—C1—C6	147.5 (2)	C4—C5—C6—C1	0.5 (3)
C6—C1—C2—C3	−0.7 (3)	C2—C1—C6—C5	0.2 (3)
N1—C1—C2—C3	−178.16 (17)	N1—C1—C6—C5	177.74 (19)
C1—C2—C3—C4	0.6 (3)	C1—N1—C7—O1	1.0 (3)
C1—C2—C3—Cl1	−179.87 (14)	C1—N1—C7—C8	−177.66 (19)
C2—C3—C4—C5	0.1 (3)	O1—C7—C8—C8i	5.9 (4)
Cl1—C3—C4—C5	−179.44 (17)	N1—C7—C8—C8i	−175.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.81 (2)	2.10 (2)	2.8946 (19)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.81 (2)	2.10 (2)	2.8946 (19)	166 (2)

Symmetry code: (i) .