Crystal structure of 1-(2,4-di-methyl-phen-yl)urea.

In the title urea derivative, C9H12N2O, the dihedral angle between the benzene ring and the mean plane of the urea group, N-C(=O)-N, is 86.6 (1)°. In the crystal, the urea O atom is involved in three N-H⋯O hydrogen bonds. Mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R (2) 2(8) ring motif. The dimers are linked by further N-H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (100).

Related literature

For general background to urea derivatives and their biological applications and properties, see: Ramalingan & Kwak (2008 ▸); Ramalingan et al. (2010 ▸); Yang et al. (2013 ▸); Safari & Gandomi-Ravandi (2014 ▸); Suzuki et al. (2013 ▸); Boulahjar et al. (2012 ▸); Zhang et al. (2014 ▸)

Experimental

Crystal data

C9H12N2O

M = 164.21

Monoclinic,

a = 14.631 (4) Å

b = 7.0633 (19) Å

c = 8.786 (2) Å

β = 93.530 (4)°

V = 906.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 292 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

8026 measured reflections

1556 independent reflections

1284 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.100

wR(F 2) = 0.349

S = 1.59

1556 reflections

119 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.87 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2001 ▸); cell refinement: SAINT (Bruker, 2001 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014027431/su5043sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027431/su5043Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027431/su5043Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014027431/su5043fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989014027431/su5043fig2.tif

A projection of the crystal packing of the title compound, along the a axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

CCDC reference: 1039538

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H12N2O	F(000) = 352
Mr = 164.21	Dx = 1.204 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.631 (4) Å	Cell parameters from 6568 reflections
b = 7.0633 (19) Å	θ = 2.8–24.6°
c = 8.786 (2) Å	µ = 0.08 mm−1
β = 93.530 (4)°	T = 292 K
V = 906.2 (4) Å3	Block, colourless
Z = 4	0.20 × 0.18 × 0.16 mm

Bruker SMART APEX CCD area-detector diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.8°
ω scans	h = −17→17
8026 measured reflections	k = −8→8
1556 independent reflections	l = −10→10
1284 reflections with I > 2σ(I)

Refinement on F2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.100	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.349	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
S = 1.59	(Δ/σ)max = 0.001
1556 reflections	Δρmax = 0.87 e Å−3
119 parameters	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.40043 (14)	0.1453 (3)	0.55423 (18)	0.0634 (8)
N1	0.32526 (19)	0.2851 (4)	0.3520 (3)	0.0709 (10)
H1	0.3186	0.2927	0.2543	0.085*
N2	0.4476 (2)	0.0982 (4)	0.3174 (3)	0.0682 (9)
H2A	0.437 (2)	0.125 (4)	0.2228 (15)	0.060 (8)*
H2B	0.4934 (19)	0.036 (5)	0.360 (4)	0.089 (11)*
C1	0.1253 (4)	0.4077 (12)	0.5679 (5)	0.1144 (17)
H1A	0.0700	0.3530	0.5912	0.137*
C2	0.1467 (3)	0.5877 (12)	0.6154 (4)	0.122 (2)
C3	0.2259 (4)	0.6656 (8)	0.5753 (5)	0.1049 (17)
H3	0.2404	0.7876	0.6085	0.126*
C4	0.2873 (2)	0.5700 (6)	0.4854 (4)	0.0794 (11)
C5	0.2652 (2)	0.3904 (5)	0.4421 (3)	0.0666 (10)
C6	0.1852 (3)	0.3106 (8)	0.4870 (4)	0.0921 (13)
H6	0.1721	0.1855	0.4606	0.111*
C7	0.0822 (4)	0.7033 (13)	0.7118 (7)	0.178 (4)
H7A	0.0806	0.6477	0.8114	0.267*
H7B	0.0216	0.7030	0.6630	0.267*
H7C	0.1040	0.8312	0.7212	0.267*
C8	0.3708 (4)	0.6517 (7)	0.4485 (7)	0.1135 (16)
H8A	0.3942	0.5853	0.3638	0.170*
H8B	0.4142	0.6433	0.5348	0.170*
H8C	0.3612	0.7822	0.4217	0.170*
C9	0.39175 (19)	0.1749 (4)	0.4154 (3)	0.0519 (8)

	U11	U22	U33	U12	U13	U23
O1	0.0806 (14)	0.0787 (15)	0.0316 (11)	0.0198 (9)	0.0094 (9)	0.0014 (7)
N1	0.0824 (18)	0.0971 (19)	0.0338 (12)	0.0270 (14)	0.0098 (11)	0.0074 (11)
N2	0.0857 (18)	0.0849 (18)	0.0353 (14)	0.0251 (13)	0.0137 (11)	0.0013 (10)
C1	0.090 (3)	0.193 (5)	0.063 (2)	0.031 (3)	0.025 (2)	0.007 (3)
C2	0.068 (2)	0.245 (7)	0.053 (2)	0.063 (3)	0.0003 (17)	−0.015 (3)
C3	0.104 (3)	0.123 (3)	0.084 (3)	0.036 (3)	−0.019 (3)	−0.036 (2)
C4	0.0685 (19)	0.105 (3)	0.064 (2)	0.0184 (17)	−0.0010 (15)	−0.0088 (16)
C5	0.0682 (19)	0.090 (2)	0.0417 (16)	0.0245 (15)	0.0069 (13)	0.0057 (13)
C6	0.086 (2)	0.128 (3)	0.064 (2)	0.018 (2)	0.0218 (17)	0.0214 (19)
C7	0.106 (4)	0.316 (9)	0.112 (4)	0.091 (5)	−0.002 (3)	−0.091 (5)
C8	0.112 (3)	0.101 (3)	0.129 (4)	−0.017 (3)	0.024 (3)	0.004 (3)
C9	0.0652 (16)	0.0572 (15)	0.0342 (14)	0.0069 (11)	0.0094 (11)	−0.0013 (9)

O1—C9	1.236 (3)	C3—C4	1.406 (6)
N1—C9	1.340 (4)	C3—H3	0.9300
N1—C5	1.428 (4)	C4—C5	1.358 (6)
N1—H1	0.8600	C4—C8	1.407 (7)
N2—C9	1.337 (4)	C5—C6	1.377 (6)
N2—H2A	0.857 (10)	C6—H6	0.9300
N2—H2B	0.863 (10)	C7—H7A	0.9600
C1—C6	1.351 (7)	C7—H7B	0.9600
C1—C2	1.368 (10)	C7—H7C	0.9600
C1—H1A	0.9300	C8—H8A	0.9600
C2—C3	1.348 (9)	C8—H8B	0.9600
C2—C7	1.541 (6)	C8—H8C	0.9600
C9—N1—C5	121.9 (2)	C6—C5—N1	120.5 (4)
C9—N1—H1	119.1	C1—C6—C5	122.2 (6)
C5—N1—H1	119.1	C1—C6—H6	118.9
C9—N2—H2A	117 (2)	C5—C6—H6	118.9
C9—N2—H2B	115 (3)	C2—C7—H7A	109.5
H2A—N2—H2B	128 (4)	C2—C7—H7B	109.5
C6—C1—C2	119.2 (6)	H7A—C7—H7B	109.5
C6—C1—H1A	120.4	C2—C7—H7C	109.5
C2—C1—H1A	120.4	H7A—C7—H7C	109.5
C3—C2—C1	119.0 (4)	H7B—C7—H7C	109.5
C3—C2—C7	119.5 (7)	C4—C8—H8A	109.5
C1—C2—C7	121.5 (6)	C4—C8—H8B	109.5
C2—C3—C4	122.7 (5)	H8A—C8—H8B	109.5
C2—C3—H3	118.7	C4—C8—H8C	109.5
C4—C3—H3	118.7	H8A—C8—H8C	109.5
C5—C4—C3	117.1 (4)	H8B—C8—H8C	109.5
C5—C4—C8	121.0 (4)	O1—C9—N2	122.5 (2)
C3—C4—C8	121.8 (4)	O1—C9—N1	122.4 (2)
C4—C5—C6	119.7 (3)	N2—C9—N1	115.1 (2)
C4—C5—N1	119.8 (3)
C6—C1—C2—C3	2.3 (7)	C8—C4—C5—N1	−2.8 (5)
C6—C1—C2—C7	−178.3 (4)	C9—N1—C5—C4	90.7 (4)
C1—C2—C3—C4	0.5 (7)	C9—N1—C5—C6	−88.6 (4)
C7—C2—C3—C4	−178.9 (4)	C2—C1—C6—C5	−4.1 (7)
C2—C3—C4—C5	−1.6 (6)	C4—C5—C6—C1	2.9 (6)
C2—C3—C4—C8	−178.1 (5)	N1—C5—C6—C1	−177.8 (3)
C3—C4—C5—C6	−0.1 (5)	C5—N1—C9—O1	6.1 (5)
C8—C4—C5—C6	176.5 (4)	C5—N1—C9—N2	−174.4 (3)
C3—C4—C5—N1	−179.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.23	2.941 (3)	140
N2—H2A···O1i	0.86 (1)	2.24 (2)	2.985 (3)	145 (3)
N2—H2B···O1ii	0.86 (1)	2.12 (1)	2.977 (3)	173 (4)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1O1i	0.86	2.23	2.941(3)	140
N2H2AO1i	0.86(1)	2.24(2)	2.985(3)	145(3)
N2H2BO1ii	0.86(1)	2.12(1)	2.977(3)	173(4)

Symmetry codes: (i) ; (ii) .