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

The carbonyl unit of the title compound, C(13)H(10)Cl(2)N(2)O, lies on a twofold rotation axis. The ring is aligned at 51.6 (1)° with respect to the N-C(=O)-N fragment. The two -NH- fragments of one mol-ecule form hydrogen bonds [2.845 (2) Å] to the C=O fragment of an adjacent mol-ecule, giving rise to the formation of a linear hydrogen-bonded chain.

Related literature

For isostructural N,N′-bis­(4-bromo­phen­yl)urea, see: Lin et al. (2004 ▶). N,N′-Bis-(4-chloro­phen­yl)urea has been isolated as a co-crystal with a phthalazinium chloride; see: Wamhoff et al. (1994 ▶). For the self-condensation of 4-chloro­phenyl isocyanate to yield the title symmetrical urea, see: Fu et al. (2007 ▶); Jimenez Blanco et al. (1999 ▶).

Experimental

Crystal data

C13H10Cl2N2O

M = 281.13

Monoclinic,

a = 27.093 (3) Å

b = 4.5768 (5) Å

c = 9.901 (1) Å

β = 96.389 (2)°

V = 1220.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 100 (2) K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.862, T max = 0.950

3703 measured reflections

1386 independent reflections

1210 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.096

S = 1.11

1386 reflections

87 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011069/tk2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011069/tk2256Isup2.hkl

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

C13H10Cl2N2O	F000 = 576
Mr = 281.13	Dx = 1.530 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1510 reflections
a = 27.093 (3) Å	θ = 3.0–28.2º
b = 4.5768 (5) Å	µ = 0.52 mm−1
c = 9.901 (1) Å	T = 100 (2) K
β = 96.389 (2)º	Block, colorless
V = 1220.1 (2) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEXII diffractometer	1386 independent reflections
Radiation source: fine-focus sealed tube	1210 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −34→27
Tmin = 0.862, Tmax = 0.950	k = −5→5
3703 measured reflections	l = −10→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0445P)2 + 1.607P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1386 reflections	Δρmax = 0.31 e Å−3
87 parameters	Δρmin = −0.29 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Cl1	0.293344 (15)	0.99597 (10)	0.33207 (4)	0.02417 (17)
O1	0.5000	0.9101 (4)	0.7500	0.0163 (4)
N1	0.46380 (5)	0.4789 (3)	0.67795 (15)	0.0149 (3)
H1	0.4640 (8)	0.292 (2)	0.691 (2)	0.024 (5)*
C1	0.5000	0.6399 (5)	0.7500	0.0130 (4)
C2	0.42311 (6)	0.6073 (3)	0.59591 (15)	0.0131 (3)
C3	0.43093 (6)	0.8150 (4)	0.49760 (16)	0.0152 (3)
H3	0.4638	0.8730	0.4854	0.018*
C4	0.39102 (6)	0.9373 (4)	0.41754 (17)	0.0175 (4)
H4	0.3963	1.0823	0.3520	0.021*
C5	0.34334 (6)	0.8455 (4)	0.43438 (16)	0.0162 (3)
C6	0.33491 (6)	0.6357 (4)	0.52957 (17)	0.0183 (4)
H6	0.3021	0.5729	0.5391	0.022*
C7	0.37498 (6)	0.5180 (4)	0.61096 (17)	0.0176 (4)
H7	0.3695	0.3754	0.6774	0.021*

	U11	U22	U33	U12	U13	U23
Cl1	0.0159 (2)	0.0299 (3)	0.0249 (3)	0.00200 (17)	−0.00584 (17)	0.00510 (17)
O1	0.0173 (8)	0.0094 (8)	0.0207 (8)	0.000	−0.0037 (6)	0.000
N1	0.0146 (7)	0.0082 (6)	0.0208 (7)	−0.0002 (5)	−0.0028 (6)	0.0007 (5)
C1	0.0128 (10)	0.0123 (11)	0.0141 (10)	0.000	0.0025 (8)	0.000
C2	0.0141 (7)	0.0104 (7)	0.0142 (7)	0.0001 (6)	−0.0006 (6)	−0.0027 (6)
C3	0.0124 (7)	0.0162 (8)	0.0167 (8)	−0.0028 (6)	0.0004 (6)	−0.0013 (6)
C4	0.0184 (8)	0.0178 (8)	0.0159 (8)	−0.0013 (6)	−0.0001 (6)	0.0016 (6)
C5	0.0138 (8)	0.0189 (8)	0.0152 (8)	0.0018 (6)	−0.0023 (6)	−0.0017 (6)
C6	0.0118 (8)	0.0233 (9)	0.0199 (8)	−0.0016 (6)	0.0024 (6)	−0.0009 (7)
C7	0.0176 (8)	0.0174 (8)	0.0178 (8)	−0.0019 (6)	0.0026 (6)	0.0026 (6)

Cl1—C5	1.741 (2)	C3—C4	1.386 (2)
O1—C1	1.237 (3)	C3—H3	0.9500
N1—C1	1.363 (2)	C4—C5	1.386 (2)
N1—C2	1.422 (2)	C4—H4	0.9500
N1—H1	0.87 (1)	C5—C6	1.382 (2)
C1—N1i	1.363 (2)	C6—C7	1.387 (2)
C2—C7	1.390 (2)	C6—H6	0.9500
C2—C3	1.393 (2)	C7—H7	0.9500
C1—N1—C2	122.9 (1)	C5—C4—C3	119.2 (2)
C1—N1—H1	118 (1)	C5—C4—H4	120.4
C2—N1—H1	119 (1)	C3—C4—H4	120.4
O1—C1—N1	122.7 (1)	C4—C5—C6	121.3 (2)
O1—C1—N1i	122.7 (1)	C4—C5—Cl1	119.0 (1)
N1—C1—N1i	114.6 (2)	C6—C5—Cl1	119.65 (13)
C7—C2—C3	119.5 (2)	C7—C6—C5	119.21 (15)
C7—C2—N1	119.6 (1)	C7—C6—H6	120.4
C3—C2—N1	120.8 (1)	C5—C6—H6	120.4
C4—C3—C2	120.4 (2)	C6—C7—C2	120.42 (15)
C4—C3—H3	119.8	C6—C7—H7	119.8
C2—C3—H3	119.8	C2—C7—H7	119.8
C2—N1—C1—O1	0.4 (2)	C3—C4—C5—C6	0.3 (3)
C2—N1—C1—N1i	−179.6 (2)	C3—C4—C5—Cl1	−179.1 (1)
C1—N1—C2—C7	−129.4 (2)	C4—C5—C6—C7	0.9 (3)
C1—N1—C2—C3	52.6 (2)	Cl1—C5—C6—C7	−179.8 (1)
C7—C2—C3—C4	1.6 (2)	C5—C6—C7—C2	−0.8 (3)
N1—C2—C3—C4	179.6 (2)	C3—C2—C7—C6	−0.5 (2)
C2—C3—C4—C5	−1.5 (2)	N1—C2—C7—C6	−178.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ii	0.87 (1)	2.05 (1)	2.845 (2)	152 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (1)	2.05 (1)	2.845 (2)	152 (2)

Symmetry code: (i) .