N,N'-Bis(4-chloro-phen-yl)maleamide.

In the crystal of the title compound, C(16)H(12)Cl(2)N(2)O(2), the two C=O groups are anti to each other, while one of them is syn and the other is anti to their adjacent C-H bonds. The two benzene rings are oriented at an inter-planar angle of 56.4 (1)°, while the dihedral angles between the central amide group (N-C-C-C-C-N) and these rings are 3.6 (1) and 54.1 (1)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into infinite chains along the a axis.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶, 2011 ▶) and on the structures of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C16H12Cl2N2O2

M = 335.18

Monoclinic,

a = 9.2397 (7) Å

b = 13.0154 (8) Å

c = 13.1239 (9) Å

β = 107.916 (9)°

V = 1501.73 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.44 × 0.44 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.830, T max = 0.872

6063 measured reflections

3065 independent reflections

2523 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.06

3065 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 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/S1600536811017636/bq2300sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017636/bq2300Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017636/bq2300Isup3.cml

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

C16H12Cl2N2O2	F(000) = 688
Mr = 335.18	Dx = 1.482 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3188 reflections
a = 9.2397 (7) Å	θ = 2.8–27.9°
b = 13.0154 (8) Å	µ = 0.44 mm−1
c = 13.1239 (9) Å	T = 293 K
β = 107.916 (9)°	Prism, dark grey
V = 1501.73 (18) Å3	0.44 × 0.44 × 0.32 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3065 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
graphite	Rint = 0.011
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→10
Tmin = 0.830, Tmax = 0.872	k = −14→16
6063 measured reflections	l = −16→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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.3163P] where P = (Fo2 + 2Fc2)/3
3065 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.24 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
Cl1	1.02985 (5)	−0.18771 (4)	0.07433 (4)	0.05576 (15)
Cl2	0.34374 (6)	0.72529 (3)	−0.01488 (4)	0.06130 (16)
O1	0.49648 (15)	0.13865 (8)	0.14544 (12)	0.0566 (4)
O2	0.10969 (14)	0.32142 (8)	0.19093 (9)	0.0449 (3)
N1	0.49484 (15)	−0.03027 (10)	0.18426 (11)	0.0380 (3)
H1N	0.4540 (19)	−0.0748 (13)	0.2131 (13)	0.046*
N2	0.30826 (16)	0.29745 (10)	0.12704 (11)	0.0393 (3)
H2N	0.3780 (18)	0.2545 (14)	0.1250 (14)	0.047*
C1	0.62405 (17)	−0.06341 (11)	0.15703 (12)	0.0349 (3)
C2	0.7035 (2)	−0.00167 (13)	0.10578 (14)	0.0479 (4)
H2	0.6734	0.0660	0.0888	0.057*
C3	0.8268 (2)	−0.04074 (14)	0.08021 (14)	0.0479 (4)
H3	0.8799	0.0007	0.0462	0.057*
C4	0.87128 (18)	−0.14080 (13)	0.10489 (12)	0.0399 (4)
C5	0.79395 (19)	−0.20323 (12)	0.15518 (13)	0.0430 (4)
H5	0.8240	−0.2711	0.1711	0.052*
C6	0.67118 (18)	−0.16405 (11)	0.18174 (13)	0.0391 (3)
H6	0.6196	−0.2057	0.2166	0.047*
C7	0.43672 (17)	0.06548 (11)	0.17594 (12)	0.0367 (3)
C8	0.29546 (19)	0.07352 (12)	0.20689 (13)	0.0410 (4)
H8	0.2649	0.0130	0.2319	0.049*
C9	0.20588 (19)	0.15430 (12)	0.20424 (13)	0.0423 (4)
H9	0.1231	0.1380	0.2274	0.051*
C10	0.20609 (17)	0.26486 (11)	0.17309 (11)	0.0346 (3)
C11	0.31503 (17)	0.40084 (11)	0.09296 (12)	0.0346 (3)
C12	0.44804 (17)	0.45625 (12)	0.13303 (12)	0.0369 (3)
H12	0.5318	0.4261	0.1825	0.044*
C13	0.45728 (18)	0.55621 (12)	0.10004 (12)	0.0386 (3)
H13	0.5469	0.5935	0.1267	0.046*
C14	0.33194 (18)	0.59989 (11)	0.02710 (12)	0.0371 (3)
C15	0.19922 (18)	0.54565 (13)	−0.01497 (13)	0.0432 (4)
H15	0.1160	0.5759	−0.0649	0.052*
C16	0.19120 (19)	0.44518 (12)	0.01807 (13)	0.0421 (4)
H16	0.1024	0.4075	−0.0102	0.051*

	U11	U22	U33	U12	U13	U23
Cl1	0.0450 (2)	0.0601 (3)	0.0653 (3)	0.0114 (2)	0.0217 (2)	−0.0056 (2)
Cl2	0.0756 (3)	0.0331 (2)	0.0800 (3)	0.0011 (2)	0.0311 (3)	0.0178 (2)
O1	0.0608 (8)	0.0259 (6)	0.1020 (10)	0.0056 (5)	0.0528 (7)	0.0123 (6)
O2	0.0515 (7)	0.0384 (6)	0.0541 (7)	0.0094 (5)	0.0300 (5)	0.0004 (5)
N1	0.0443 (7)	0.0262 (6)	0.0500 (7)	0.0015 (5)	0.0242 (6)	0.0079 (5)
N2	0.0467 (8)	0.0271 (6)	0.0530 (8)	0.0088 (6)	0.0282 (6)	0.0076 (6)
C1	0.0381 (8)	0.0284 (7)	0.0394 (8)	0.0016 (6)	0.0139 (6)	0.0004 (6)
C2	0.0580 (10)	0.0334 (8)	0.0624 (10)	0.0103 (8)	0.0336 (9)	0.0138 (8)
C3	0.0537 (10)	0.0436 (9)	0.0549 (10)	0.0034 (8)	0.0293 (8)	0.0084 (8)
C4	0.0377 (8)	0.0421 (9)	0.0393 (8)	0.0044 (7)	0.0108 (6)	−0.0068 (7)
C5	0.0449 (9)	0.0310 (8)	0.0511 (9)	0.0061 (7)	0.0116 (7)	−0.0008 (7)
C6	0.0435 (8)	0.0282 (7)	0.0463 (8)	−0.0024 (6)	0.0147 (7)	0.0022 (6)
C7	0.0425 (8)	0.0262 (7)	0.0460 (8)	0.0014 (6)	0.0206 (7)	0.0033 (6)
C8	0.0500 (9)	0.0293 (7)	0.0523 (9)	0.0001 (7)	0.0285 (8)	0.0075 (7)
C9	0.0490 (9)	0.0373 (8)	0.0515 (9)	0.0015 (7)	0.0315 (8)	0.0064 (7)
C10	0.0415 (8)	0.0313 (7)	0.0353 (7)	0.0034 (6)	0.0180 (6)	−0.0005 (6)
C11	0.0433 (8)	0.0271 (7)	0.0403 (8)	0.0060 (6)	0.0231 (6)	0.0030 (6)
C12	0.0389 (8)	0.0381 (8)	0.0364 (8)	0.0076 (7)	0.0154 (6)	0.0060 (6)
C13	0.0417 (8)	0.0358 (8)	0.0421 (8)	−0.0028 (7)	0.0183 (7)	−0.0009 (6)
C14	0.0489 (9)	0.0269 (7)	0.0430 (8)	0.0043 (6)	0.0252 (7)	0.0052 (6)
C15	0.0414 (8)	0.0396 (9)	0.0486 (9)	0.0087 (7)	0.0140 (7)	0.0113 (7)
C16	0.0386 (8)	0.0350 (8)	0.0525 (9)	−0.0001 (7)	0.0136 (7)	0.0040 (7)

Cl1—C4	1.7440 (16)	C5—H5	0.9300
Cl2—C14	1.7367 (15)	C6—H6	0.9300
O1—C7	1.2280 (18)	C7—C8	1.485 (2)
O2—C10	1.2322 (18)	C8—C9	1.332 (2)
N1—C7	1.3481 (19)	C8—H8	0.9300
N1—C1	1.4149 (19)	C9—C10	1.496 (2)
N1—H1N	0.843 (14)	C9—H9	0.9300
N2—C10	1.3369 (19)	C11—C12	1.382 (2)
N2—C11	1.4255 (19)	C11—C16	1.384 (2)
N2—H2N	0.860 (14)	C12—C13	1.382 (2)
C1—C6	1.387 (2)	C12—H12	0.9300
C1—C2	1.393 (2)	C13—C14	1.378 (2)
C2—C3	1.380 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.375 (2)
C3—C4	1.374 (2)	C15—C16	1.387 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.377 (2)	C16—H16	0.9300
C5—C6	1.383 (2)
C7—N1—C1	127.41 (13)	C9—C8—C7	129.78 (14)
C7—N1—H1N	116.8 (13)	C9—C8—H8	115.1
C1—N1—H1N	115.7 (13)	C7—C8—H8	115.1
C10—N2—C11	123.13 (13)	C8—C9—C10	135.51 (14)
C10—N2—H2N	116.6 (13)	C8—C9—H9	112.2
C11—N2—H2N	119.9 (13)	C10—C9—H9	112.2
C6—C1—C2	118.92 (14)	O2—C10—N2	123.26 (14)
C6—C1—N1	117.23 (13)	O2—C10—C9	117.45 (13)
C2—C1—N1	123.84 (14)	N2—C10—C9	119.29 (13)
C3—C2—C1	120.13 (15)	C12—C11—C16	119.78 (14)
C3—C2—H2	119.9	C12—C11—N2	119.54 (14)
C1—C2—H2	119.9	C16—C11—N2	120.66 (14)
C4—C3—C2	120.08 (16)	C11—C12—C13	120.37 (14)
C4—C3—H3	120.0	C11—C12—H12	119.8
C2—C3—H3	120.0	C13—C12—H12	119.8
C3—C4—C5	120.71 (15)	C14—C13—C12	119.10 (15)
C3—C4—Cl1	119.28 (13)	C14—C13—H13	120.5
C5—C4—Cl1	120.00 (13)	C12—C13—H13	120.5
C4—C5—C6	119.34 (15)	C15—C14—C13	121.49 (14)
C4—C5—H5	120.3	C15—C14—Cl2	119.37 (12)
C6—C5—H5	120.3	C13—C14—Cl2	119.12 (12)
C5—C6—C1	120.82 (15)	C14—C15—C16	119.04 (15)
C5—C6—H6	119.6	C14—C15—H15	120.5
C1—C6—H6	119.6	C16—C15—H15	120.5
O1—C7—N1	122.38 (14)	C11—C16—C15	120.21 (15)
O1—C7—C8	123.75 (14)	C11—C16—H16	119.9
N1—C7—C8	113.87 (13)	C15—C16—H16	119.9
C7—N1—C1—C6	174.16 (15)	C11—N2—C10—O2	−0.6 (3)
C7—N1—C1—C2	−7.0 (3)	C11—N2—C10—C9	178.80 (14)
C6—C1—C2—C3	0.1 (3)	C8—C9—C10—O2	−173.19 (19)
N1—C1—C2—C3	−178.74 (16)	C8—C9—C10—N2	7.4 (3)
C1—C2—C3—C4	0.2 (3)	C10—N2—C11—C12	122.66 (17)
C2—C3—C4—C5	0.0 (3)	C10—N2—C11—C16	−59.1 (2)
C2—C3—C4—Cl1	−178.68 (14)	C16—C11—C12—C13	1.0 (2)
C3—C4—C5—C6	−0.6 (2)	N2—C11—C12—C13	179.29 (13)
Cl1—C4—C5—C6	178.10 (12)	C11—C12—C13—C14	0.3 (2)
C4—C5—C6—C1	0.9 (2)	C12—C13—C14—C15	−1.3 (2)
C2—C1—C6—C5	−0.7 (2)	C12—C13—C14—Cl2	−179.70 (11)
N1—C1—C6—C5	178.25 (14)	C13—C14—C15—C16	0.9 (2)
C1—N1—C7—O1	−2.6 (3)	Cl2—C14—C15—C16	179.31 (12)
C1—N1—C7—C8	177.38 (14)	C12—C11—C16—C15	−1.4 (2)
O1—C7—C8—C9	3.0 (3)	N2—C11—C16—C15	−179.66 (14)
N1—C7—C8—C9	−176.98 (17)	C14—C15—C16—C11	0.5 (2)
C7—C8—C9—C10	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (1)	2.05 (2)	2.8836 (16)	169.(2)
N2—H2N···O1	0.86 (1)	1.83 (2)	2.6639 (17)	162.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (1)	2.05 (2)	2.8836 (16)	169 (2)
N2—H2N⋯O1	0.86 (1)	1.83 (2)	2.6639 (17)	162 (2)

Symmetry code: (i) .