1-(3-Chloro-phen-yl)-3-(4-nitro-phen-yl)urea.

In the title compound, C(13)H(10)ClN(3)O(3), prepared by the reaction of 1-chloro-3-isocyanato-benzene with 4-nitro-benzenamine, the two substituent benzene rings are roughly coplanar [inter-ring dihedral angle = 8.70 (7)°]. In the crystal, mol-ecules make cyclic inter-molecular associations through two urea-nitro N-H⋯O hydrogen bonds, forming a chain structure [give chain direction] in which there are also weak inter-molecular C-H⋯Cl inter-actions. The urea O atom has only intra-molecular aromatic ring C-H⋯O associations.

Related literature

For the bioactivity of urea derivatives, see: Wang et al. (2001 ▶); Song et al. (2008 ▶); Yip et al. (1986 ▶); Liu et al. (2005 ▶).

Experimental

Crystal data

C13H10ClN3O3

M = 291.69

Monoclinic,

a = 8.3410 (13) Å

b = 12.5410 (18) Å

c = 12.1120 (16) Å

β = 99.866 (5)°

V = 1248.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 113 K

0.24 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ▶) T min = 0.928, T max = 0.939

15672 measured reflections

2964 independent reflections

2396 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.04

2964 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040201/zs2070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040201/zs2070Isup2.hkl

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

C13H10ClN3O3	F(000) = 600
Mr = 291.69	Dx = 1.552 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 4351 reflections
a = 8.3410 (13) Å	θ = 1.6–27.9°
b = 12.5410 (18) Å	µ = 0.32 mm−1
c = 12.1120 (16) Å	T = 113 K
β = 99.866 (5)°	Prism, colorless
V = 1248.2 (3) Å3	0.24 × 0.22 × 0.20 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	2964 independent reflections
Radiation source: rotating anode	2396 reflections with I > 2σ(I)
multilayer	Rint = 0.041
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −16→16
Tmin = 0.928, Tmax = 0.939	l = −15→15
15672 measured reflections

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) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0589P)2] where P = (Fo2 + 2Fc2)/3
2964 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.24 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
Cl1	0.22721 (4)	0.01383 (3)	0.53821 (3)	0.02970 (12)
O1	0.31522 (10)	0.39764 (6)	0.45111 (7)	0.0187 (2)
O2	0.55192 (10)	0.80112 (7)	0.13369 (7)	0.0218 (2)
O3	0.49009 (10)	0.93629 (7)	0.22967 (7)	0.0221 (2)
N1	0.17484 (13)	0.41897 (8)	0.59747 (9)	0.0177 (2)
N2	0.23742 (12)	0.56468 (8)	0.50077 (9)	0.0171 (2)
N3	0.49071 (11)	0.83930 (8)	0.21073 (8)	0.0173 (2)
C1	0.24839 (13)	0.45459 (9)	0.51100 (10)	0.0152 (2)
C2	0.15298 (14)	0.31274 (9)	0.62949 (10)	0.0153 (2)
C3	0.20047 (14)	0.22475 (9)	0.57217 (10)	0.0175 (3)
H3	0.2525	0.2338	0.5089	0.021*
C4	0.16951 (15)	0.12397 (9)	0.61013 (10)	0.0191 (3)
C5	0.09396 (15)	0.10706 (10)	0.70225 (10)	0.0205 (3)
H5	0.0743	0.0369	0.7262	0.025*
C6	0.04799 (14)	0.19542 (10)	0.75831 (10)	0.0198 (3)
H6	−0.0042	0.1858	0.8215	0.024*
C7	0.07749 (14)	0.29736 (9)	0.72298 (10)	0.0175 (3)
H7	0.0463	0.3573	0.7624	0.021*
C8	0.29852 (14)	0.62892 (9)	0.42460 (10)	0.0151 (2)
C9	0.34844 (14)	0.59016 (9)	0.32687 (10)	0.0177 (3)
H9	0.3407	0.5162	0.3096	0.021*
C10	0.40879 (14)	0.66018 (10)	0.25622 (10)	0.0178 (3)
H10	0.4434	0.6348	0.1903	0.021*
C11	0.41844 (14)	0.76771 (9)	0.28220 (10)	0.0157 (2)
C12	0.36528 (14)	0.80862 (9)	0.37613 (10)	0.0174 (3)
H12	0.3702	0.8830	0.3913	0.021*
C13	0.30537 (14)	0.73906 (10)	0.44672 (10)	0.0174 (3)
H13	0.2681	0.7657	0.5113	0.021*
H1	0.1324 (18)	0.4614 (13)	0.6334 (14)	0.035 (5)*
H2	0.1933 (16)	0.5948 (12)	0.5489 (12)	0.024 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0455 (2)	0.01399 (17)	0.0309 (2)	0.00282 (13)	0.01006 (16)	−0.00398 (12)
O1	0.0246 (5)	0.0139 (4)	0.0200 (4)	0.0023 (3)	0.0111 (4)	−0.0004 (3)
O2	0.0264 (5)	0.0220 (5)	0.0196 (4)	−0.0022 (4)	0.0115 (4)	0.0009 (4)
O3	0.0290 (5)	0.0128 (4)	0.0259 (5)	−0.0023 (3)	0.0089 (4)	0.0026 (3)
N1	0.0245 (6)	0.0118 (5)	0.0195 (5)	0.0016 (4)	0.0114 (4)	−0.0003 (4)
N2	0.0244 (6)	0.0115 (5)	0.0182 (5)	0.0011 (4)	0.0120 (4)	−0.0003 (4)
N3	0.0171 (5)	0.0172 (5)	0.0178 (5)	−0.0014 (4)	0.0035 (4)	0.0030 (4)
C1	0.0159 (6)	0.0137 (5)	0.0164 (5)	−0.0012 (4)	0.0037 (4)	0.0008 (4)
C2	0.0151 (6)	0.0132 (5)	0.0173 (6)	−0.0008 (4)	0.0019 (5)	0.0017 (4)
C3	0.0191 (6)	0.0168 (6)	0.0171 (6)	0.0007 (5)	0.0042 (5)	0.0000 (5)
C4	0.0220 (6)	0.0141 (6)	0.0202 (6)	0.0015 (5)	0.0011 (5)	−0.0023 (5)
C5	0.0235 (6)	0.0147 (6)	0.0228 (6)	−0.0032 (5)	0.0020 (5)	0.0037 (5)
C6	0.0197 (6)	0.0209 (6)	0.0192 (6)	−0.0023 (5)	0.0045 (5)	0.0043 (5)
C7	0.0187 (6)	0.0165 (6)	0.0179 (6)	0.0004 (5)	0.0050 (5)	0.0009 (4)
C8	0.0147 (6)	0.0142 (6)	0.0171 (5)	−0.0001 (4)	0.0046 (4)	0.0016 (4)
C9	0.0223 (6)	0.0137 (5)	0.0181 (6)	−0.0004 (5)	0.0067 (5)	−0.0010 (4)
C10	0.0208 (6)	0.0168 (6)	0.0172 (6)	0.0012 (5)	0.0072 (5)	−0.0006 (5)
C11	0.0160 (6)	0.0150 (6)	0.0168 (6)	−0.0009 (4)	0.0049 (5)	0.0034 (4)
C12	0.0205 (6)	0.0132 (5)	0.0194 (6)	−0.0001 (4)	0.0056 (5)	0.0000 (4)
C13	0.0212 (6)	0.0148 (6)	0.0176 (6)	0.0010 (5)	0.0076 (5)	−0.0010 (4)

Cl1—C4	1.7441 (12)	C5—C6	1.3876 (17)
O1—C1	1.2187 (14)	C5—H5	0.9500
O2—N3	1.2345 (13)	C6—C7	1.3835 (16)
O3—N3	1.2380 (13)	C6—H6	0.9500
N1—C1	1.3759 (15)	C7—H7	0.9500
N1—C2	1.4080 (14)	C8—C13	1.4064 (16)
N1—H1	0.806 (16)	C8—C9	1.4070 (15)
N2—C8	1.3860 (15)	C9—C10	1.3800 (16)
N2—C1	1.3879 (15)	C9—H9	0.9500
N2—H2	0.832 (14)	C10—C11	1.3840 (17)
N3—C11	1.4483 (14)	C10—H10	0.9500
C2—C3	1.3968 (16)	C11—C12	1.3882 (16)
C2—C7	1.4001 (16)	C12—C13	1.3741 (16)
C3—C4	1.3842 (16)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3885 (16)
C1—N1—C2	127.77 (10)	C7—C6—C5	120.52 (11)
C1—N1—H1	119.4 (12)	C7—C6—H6	119.7
C2—N1—H1	112.7 (12)	C5—C6—H6	119.7
C8—N2—C1	127.69 (10)	C6—C7—C2	120.39 (11)
C8—N2—H2	117.4 (10)	C6—C7—H7	119.8
C1—N2—H2	114.8 (10)	C2—C7—H7	119.8
O2—N3—O3	122.45 (10)	N2—C8—C13	116.84 (10)
O2—N3—C11	118.67 (10)	N2—C8—C9	123.70 (11)
O3—N3—C11	118.88 (10)	C13—C8—C9	119.44 (11)
O1—C1—N1	124.88 (11)	C10—C9—C8	119.59 (11)
O1—C1—N2	124.04 (11)	C10—C9—H9	120.2
N1—C1—N2	111.08 (10)	C8—C9—H9	120.2
C3—C2—C7	119.89 (11)	C9—C10—C11	119.48 (11)
C3—C2—N1	123.33 (11)	C9—C10—H10	120.3
C7—C2—N1	116.78 (10)	C11—C10—H10	120.3
C4—C3—C2	118.12 (11)	C10—C11—C12	122.16 (11)
C4—C3—H3	120.9	C10—C11—N3	118.82 (10)
C2—C3—H3	120.9	C12—C11—N3	119.00 (11)
C3—C4—C5	122.85 (11)	C13—C12—C11	118.46 (11)
C3—C4—Cl1	118.29 (9)	C13—C12—H12	120.8
C5—C4—Cl1	118.85 (10)	C11—C12—H12	120.8
C6—C5—C4	118.22 (11)	C12—C13—C8	120.81 (11)
C6—C5—H5	120.9	C12—C13—H13	119.6
C4—C5—H5	120.9	C8—C13—H13	119.6
C2—N1—C1—O1	−4.21 (19)	C1—N2—C8—C13	−165.69 (11)
C2—N1—C1—N2	176.06 (11)	C1—N2—C8—C9	16.15 (18)
C8—N2—C1—O1	−0.55 (19)	N2—C8—C9—C10	−179.59 (11)
C8—N2—C1—N1	179.19 (11)	C13—C8—C9—C10	2.29 (17)
C1—N1—C2—C3	−2.48 (19)	C8—C9—C10—C11	−0.37 (17)
C1—N1—C2—C7	178.39 (11)	C9—C10—C11—C12	−1.71 (18)
C7—C2—C3—C4	0.46 (17)	C9—C10—C11—N3	176.47 (10)
N1—C2—C3—C4	−178.64 (11)	O2—N3—C11—C10	−5.16 (16)
C2—C3—C4—C5	−0.09 (18)	O3—N3—C11—C10	175.45 (10)
C2—C3—C4—Cl1	179.53 (9)	O2—N3—C11—C12	173.09 (10)
C3—C4—C5—C6	−0.06 (19)	O3—N3—C11—C12	−6.30 (16)
Cl1—C4—C5—C6	−179.68 (9)	C10—C11—C12—C13	1.80 (17)
C4—C5—C6—C7	−0.16 (18)	N3—C11—C12—C13	−176.39 (10)
C5—C6—C7—C2	0.54 (17)	C11—C12—C13—C8	0.20 (17)
C3—C2—C7—C6	−0.69 (17)	N2—C8—C13—C12	179.54 (10)
N1—C2—C7—C6	178.47 (11)	C9—C8—C13—C12	−2.22 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.807 (16)	2.211 (16)	3.0131 (14)	172.8 (16)
N2—H2···O2i	0.832 (14)	2.136 (14)	2.9448 (14)	164.1 (14)
C3—H3···O1	0.95	2.26	2.8720 (15)	121
C9—H9···O1	0.95	2.31	2.8833 (15)	118
C12—H12···Cl1ii	0.95	2.83	3.5465 (13)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.807 (16)	2.211 (16)	3.0131 (14)	172.8 (16)
N2—H2⋯O2i	0.832 (14)	2.136 (14)	2.9448 (14)	164.1 (14)
C3—H3⋯O1	0.95	2.26	2.8720 (15)	121
C9—H9⋯O1	0.95	2.31	2.8833 (15)	118
C12—H12⋯Cl1ii	0.95	2.83	3.5465 (13)	133

Symmetry codes: (i) ; (ii) .