N,N'-Bis(2-chloro-phen-yl)succinamide.

There is one half-mol-ecule in the asymmetric unit of the title compound, C(16)H(14)Cl(2)N(2)O(2), with a center of symmetry at the mid-point of the central C-C bond. The N-H and C=O bonds in the C-NH-C(O)-C fragment are anti to each other and the amide O atom is anti to the H atoms attached to the adjacent C atoms. However, the conformation of the N-H bond in the amide fragments is syn to the ortho-chloro groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) fragment is 47.0 (2)°. In the crystal, a series of N-H⋯O inter-molecular hydrogen bonds link the mol-ecules into chains along the b axis.

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 ▶) and on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶). For a similar structure, see Pierrot et al. (1984 ▶).

Experimental

Crystal data

C16H14Cl2N2O2

M = 337.19

Monoclinic,

a = 4.820 (2) Å

b = 11.445 (3) Å

c = 14.242 (4) Å

β = 98.10 (3)°

V = 777.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.44 × 0.08 × 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 = 0.835, T max = 0.983

2501 measured reflections

1563 independent reflections

900 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.139

S = 1.16

1563 reflections

103 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.22 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/S1600536811013407/fl2341sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013407/fl2341Isup2.hkl

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

C16H14Cl2N2O2	F(000) = 348
Mr = 337.19	Dx = 1.440 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 475 reflections
a = 4.820 (2) Å	θ = 2.9–27.8°
b = 11.445 (3) Å	µ = 0.43 mm−1
c = 14.242 (4) Å	T = 293 K
β = 98.10 (3)°	Needle, colourless
V = 777.8 (4) Å3	0.44 × 0.08 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1563 independent reflections
Radiation source: fine-focus sealed tube	900 reflections with I > 2σ(I)
graphite	Rint = 0.038
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→5
Tmin = 0.835, Tmax = 0.983	k = −10→14
2501 measured reflections	l = −17→6

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0376P)2 + 0.5594P] where P = (Fo2 + 2Fc2)/3
1563 reflections	(Δ/σ)max = 0.002
103 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) 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
C1	−0.0199 (7)	0.1565 (3)	0.8739 (3)	0.0360 (10)
C2	0.0563 (7)	0.1162 (3)	0.7889 (3)	0.0372 (10)
C3	−0.0371 (9)	0.0099 (4)	0.7516 (3)	0.0486 (11)
H3	0.0193	−0.0164	0.6955	0.058*
C4	−0.2122 (9)	−0.0569 (4)	0.7966 (4)	0.0584 (13)
H4	−0.2760	−0.1283	0.7710	0.070*
C5	−0.2940 (10)	−0.0188 (4)	0.8796 (4)	0.0596 (13)
H5	−0.4151	−0.0639	0.9099	0.072*
C6	−0.1964 (9)	0.0869 (4)	0.9185 (3)	0.0490 (11)
H6	−0.2504	0.1114	0.9755	0.059*
C7	−0.0733 (8)	0.3461 (4)	0.9476 (3)	0.0392 (10)
C8	0.0844 (9)	0.4520 (4)	0.9871 (4)	0.0621 (14)
H8A	0.2115	0.4287	1.0430	0.075*
H8B	0.1977	0.4799	0.9406	0.075*
N1	0.0847 (6)	0.2633 (3)	0.9133 (2)	0.0392 (9)
H1N	0.251 (5)	0.287 (3)	0.909 (3)	0.047*
O1	−0.3255 (5)	0.3362 (2)	0.9469 (2)	0.0506 (9)
Cl1	0.2688 (2)	0.20113 (11)	0.72809 (8)	0.0586 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0217 (18)	0.040 (2)	0.045 (2)	0.0046 (18)	−0.0007 (18)	−0.002 (2)
C2	0.028 (2)	0.037 (2)	0.046 (3)	0.0015 (19)	0.0026 (18)	−0.006 (2)
C3	0.041 (2)	0.050 (3)	0.052 (3)	0.004 (2)	−0.002 (2)	−0.016 (2)
C4	0.046 (3)	0.039 (3)	0.088 (4)	−0.006 (2)	0.002 (3)	−0.014 (3)
C5	0.052 (3)	0.047 (3)	0.081 (4)	−0.013 (2)	0.012 (3)	0.002 (3)
C6	0.043 (3)	0.051 (3)	0.054 (3)	−0.002 (2)	0.012 (2)	−0.001 (2)
C7	0.025 (2)	0.049 (3)	0.043 (2)	−0.0019 (19)	0.0035 (18)	−0.010 (2)
C8	0.030 (2)	0.061 (3)	0.096 (4)	−0.005 (2)	0.013 (2)	−0.040 (3)
N1	0.0212 (17)	0.035 (2)	0.063 (2)	−0.0055 (16)	0.0102 (17)	−0.0159 (17)
O1	0.0202 (14)	0.0527 (19)	0.079 (2)	−0.0032 (13)	0.0082 (14)	−0.0217 (16)
Cl1	0.0566 (7)	0.0597 (7)	0.0648 (8)	−0.0032 (7)	0.0266 (6)	−0.0035 (7)

C1—C6	1.384 (5)	C5—H5	0.9300
C1—C2	1.393 (5)	C6—H6	0.9300
C1—N1	1.408 (5)	C7—O1	1.220 (4)
C2—C3	1.377 (5)	C7—N1	1.350 (5)
C2—Cl1	1.730 (4)	C7—C8	1.498 (5)
C3—C4	1.364 (6)	C8—C8i	1.445 (8)
C3—H3	0.9300	C8—H8A	0.9700
C4—C5	1.369 (6)	C8—H8B	0.9700
C4—H4	0.9300	N1—H1N	0.857 (19)
C5—C6	1.384 (6)
C6—C1—C2	117.6 (4)	C5—C6—C1	121.0 (4)
C6—C1—N1	121.7 (4)	C5—C6—H6	119.5
C2—C1—N1	120.7 (4)	C1—C6—H6	119.5
C3—C2—C1	121.1 (4)	O1—C7—N1	123.0 (4)
C3—C2—Cl1	119.2 (3)	O1—C7—C8	122.1 (4)
C1—C2—Cl1	119.7 (3)	N1—C7—C8	115.0 (3)
C4—C3—C2	120.3 (4)	C8i—C8—C7	115.9 (4)
C4—C3—H3	119.9	C8i—C8—H8A	108.3
C2—C3—H3	119.9	C7—C8—H8A	108.3
C3—C4—C5	120.0 (4)	C8i—C8—H8B	108.3
C3—C4—H4	120.0	C7—C8—H8B	108.3
C5—C4—H4	120.0	H8A—C8—H8B	107.4
C4—C5—C6	120.1 (4)	C7—N1—C1	124.4 (3)
C4—C5—H5	120.0	C7—N1—H1N	113 (3)
C6—C5—H5	120.0	C1—N1—H1N	122 (3)
C6—C1—C2—C3	−1.1 (6)	C2—C1—C6—C5	−0.2 (6)
N1—C1—C2—C3	177.7 (4)	N1—C1—C6—C5	−178.9 (4)
C6—C1—C2—Cl1	178.3 (3)	O1—C7—C8—C8i	−7.8 (9)
N1—C1—C2—Cl1	−3.0 (5)	N1—C7—C8—C8i	172.2 (5)
C1—C2—C3—C4	1.4 (6)	O1—C7—N1—C1	−0.6 (7)
Cl1—C2—C3—C4	−177.9 (3)	C8—C7—N1—C1	179.3 (4)
C2—C3—C4—C5	−0.5 (7)	C6—C1—N1—C7	−47.6 (6)
C3—C4—C5—C6	−0.8 (7)	C2—C1—N1—C7	133.7 (4)
C4—C5—C6—C1	1.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.86 (2)	2.11 (2)	2.936 (4)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (2)	2.11 (2)	2.936 (4)	161 (3)

Symmetry code: (i) .