1-(3-Phenyl-prop-yl)urea.

In the crystal of the title compound, C(10)H(14)N(2)O, double supra-molecular layers of PhCH(2)CH(2)CH(2)NHC(O)NH(2) are formed parallel to the bc plane by inter-molecular N-H⋯O hydrogen bonding, with R(2) (2)(8) and R(2) (1)(6) motifs in the b- and c-axis directions, respectively. The mean plane of the C(ar)-C-C group makes a dihedral angle of 84.8 (2)° with the benzene ring.

Related literature

For related structural information see Bernstein et al. (1995 ▶). For background chemistry, see: Gray et al. (2005 ▶); Hua & Woollins (2009 ▶); Renodon-Cornière et al. (2002 ▶).

Experimental

Crystal data

C10H14N2O

M = 178.23

Monoclinic,

a = 17.002 (4) Å

b = 6.4953 (15) Å

c = 9.171 (2) Å

β = 91.401 (8)°

V = 1012.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 93 K

0.25 × 0.04 × 0.03 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 ▶) T min = 0.981, T max = 0.998

6696 measured reflections

2126 independent reflections

1360 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.144

S = 1.03

2126 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038501/bt5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038501/bt5070Isup2.hkl

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

C10H14N2O	F(000) = 384
Mr = 178.23	Dx = 1.169 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.002 (4) Å	Cell parameters from 2697 reflections
b = 6.4953 (15) Å	θ = 2.4–28.1°
c = 9.171 (2) Å	µ = 0.08 mm−1
β = 91.401 (8)°	T = 93 K
V = 1012.5 (4) Å3	Platelet, colorless
Z = 4	0.25 × 0.04 × 0.03 mm

Rigaku Mercury CCD diffractometer	2126 independent reflections
Radiation source: rotating anode	1360 reflections with I > 2σ(I)
confocal	Rint = 0.038
Detector resolution: 0.83 pixels mm-1	θmax = 28.5°, θmin = 3.4°
ω scans	h = −16→20
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)	k = −8→7
Tmin = 0.981, Tmax = 0.998	l = −9→11
6696 measured reflections

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2126 reflections	Δρmax = 0.23 e Å−3
122 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (5)

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
O1	0.56839 (7)	1.2854 (2)	0.55596 (11)	0.0367 (4)
N2	0.61033 (9)	1.1114 (2)	0.35832 (16)	0.0321 (4)
C5	0.81085 (11)	0.5672 (3)	0.32854 (16)	0.0325 (5)
N1	0.54532 (10)	1.4186 (3)	0.33030 (14)	0.0401 (5)
H1A	0.5219	1.5274	0.3665	0.048*
H1B	0.5499	1.4060	0.2353	0.048*
C2	0.64786 (11)	0.9469 (3)	0.44128 (17)	0.0342 (5)
H2A	0.6075	0.8490	0.4749	0.041*
H2B	0.6756	1.0048	0.5282	0.041*
C10	0.79059 (12)	0.3888 (3)	0.25485 (18)	0.0396 (5)
H10	0.7413	0.3258	0.2721	0.047*
C6	0.88327 (12)	0.6552 (3)	0.3003 (2)	0.0451 (6)
H6	0.8987	0.7777	0.3497	0.054*
C3	0.70581 (11)	0.8358 (3)	0.34725 (18)	0.0338 (5)
H3A	0.7425	0.9378	0.3063	0.041*
H3B	0.6768	0.7703	0.2646	0.041*
C4	0.75349 (11)	0.6713 (3)	0.42853 (18)	0.0354 (5)
H4A	0.7828	0.7353	0.5114	0.042*
H4B	0.7174	0.5671	0.4684	0.042*
C9	0.84088 (13)	0.3000 (3)	0.1561 (2)	0.0457 (6)
H9	0.8259	0.1765	0.1074	0.055*
C8	0.91183 (13)	0.3890 (4)	0.1284 (2)	0.0475 (6)
H8	0.9459	0.3288	0.0598	0.057*
C7	0.93348 (13)	0.5670 (4)	0.2009 (2)	0.0533 (6)
H7	0.9828	0.6294	0.1828	0.064*
C1	0.57407 (10)	1.2717 (3)	0.42002 (17)	0.0305 (5)
H2	0.6095 (11)	1.110 (3)	0.264 (2)	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0480 (9)	0.0409 (8)	0.0211 (7)	0.0078 (6)	0.0029 (5)	−0.0016 (5)
N2	0.0408 (10)	0.0356 (9)	0.0199 (8)	0.0082 (7)	0.0011 (6)	−0.0016 (6)
C5	0.0355 (11)	0.0340 (11)	0.0280 (9)	0.0034 (8)	0.0013 (7)	0.0026 (7)
N1	0.0575 (12)	0.0397 (10)	0.0232 (8)	0.0145 (8)	0.0041 (7)	−0.0004 (6)
C2	0.0405 (12)	0.0357 (11)	0.0264 (9)	0.0050 (8)	0.0023 (7)	0.0009 (7)
C10	0.0426 (13)	0.0348 (11)	0.0415 (11)	−0.0006 (9)	0.0055 (8)	−0.0006 (8)
C6	0.0402 (13)	0.0472 (13)	0.0480 (12)	−0.0050 (10)	0.0030 (9)	−0.0113 (9)
C3	0.0385 (12)	0.0351 (11)	0.0281 (10)	0.0043 (8)	0.0043 (7)	−0.0005 (7)
C4	0.0397 (12)	0.0363 (11)	0.0303 (10)	0.0037 (8)	0.0008 (8)	0.0013 (7)
C9	0.0541 (14)	0.0392 (12)	0.0440 (12)	0.0029 (10)	0.0029 (9)	−0.0079 (9)
C8	0.0447 (14)	0.0572 (15)	0.0408 (12)	0.0130 (11)	0.0071 (9)	−0.0058 (10)
C7	0.0388 (13)	0.0659 (16)	0.0557 (13)	−0.0033 (11)	0.0092 (10)	−0.0079 (11)
C1	0.0327 (11)	0.0361 (11)	0.0228 (10)	0.0010 (8)	0.0022 (7)	0.0001 (7)

O1—C1	1.2559 (18)	C10—H10	0.9500
N2—C1	1.342 (2)	C6—C7	1.387 (3)
N2—C2	1.450 (2)	C6—H6	0.9500
N2—H2	0.863 (18)	C3—C4	1.525 (2)
C5—C10	1.380 (3)	C3—H3A	0.9900
C5—C6	1.388 (3)	C3—H3B	0.9900
C5—C4	1.514 (3)	C4—H4A	0.9900
N1—C1	1.344 (2)	C4—H4B	0.9900
N1—H1A	0.8800	C9—C8	1.367 (3)
N1—H1B	0.8800	C9—H9	0.9500
C2—C3	1.509 (2)	C8—C7	1.379 (3)
C2—H2A	0.9900	C8—H8	0.9500
C2—H2B	0.9900	C7—H7	0.9500
C10—C9	1.386 (3)
C1—N2—C2	123.43 (14)	C4—C3—H3A	108.8
C1—N2—H2	115.5 (12)	C2—C3—H3B	108.8
C2—N2—H2	121.1 (12)	C4—C3—H3B	108.8
C10—C5—C6	117.78 (17)	H3A—C3—H3B	107.7
C10—C5—C4	120.97 (17)	C5—C4—C3	111.07 (14)
C6—C5—C4	121.11 (17)	C5—C4—H4A	109.4
C1—N1—H1A	120.0	C3—C4—H4A	109.4
C1—N1—H1B	120.0	C5—C4—H4B	109.4
H1A—N1—H1B	120.0	C3—C4—H4B	109.4
N2—C2—C3	109.73 (13)	H4A—C4—H4B	108.0
N2—C2—H2A	109.7	C8—C9—C10	120.42 (19)
C3—C2—H2A	109.7	C8—C9—H9	119.8
N2—C2—H2B	109.7	C10—C9—H9	119.8
C3—C2—H2B	109.7	C9—C8—C7	119.43 (18)
H2A—C2—H2B	108.2	C9—C8—H8	120.3
C5—C10—C9	121.23 (19)	C7—C8—H8	120.3
C5—C10—H10	119.4	C8—C7—C6	120.1 (2)
C9—C10—H10	119.4	C8—C7—H7	120.0
C7—C6—C5	121.1 (2)	C6—C7—H7	120.0
C7—C6—H6	119.5	O1—C1—N2	121.38 (15)
C5—C6—H6	119.5	O1—C1—N1	121.44 (16)
C2—C3—C4	113.74 (14)	N2—C1—N1	117.17 (14)
C2—C3—H3A	108.8
C1—N2—C2—C3	−160.22 (17)	C2—C3—C4—C5	−179.52 (16)
C6—C5—C10—C9	0.2 (3)	C5—C10—C9—C8	−0.6 (3)
C4—C5—C10—C9	175.84 (17)	C10—C9—C8—C7	0.8 (3)
C10—C5—C6—C7	0.2 (3)	C9—C8—C7—C6	−0.4 (3)
C4—C5—C6—C7	−175.50 (18)	C5—C6—C7—C8	0.0 (3)
N2—C2—C3—C4	175.12 (15)	C2—N2—C1—O1	−2.2 (3)
C10—C5—C4—C3	−92.9 (2)	C2—N2—C1—N1	176.63 (16)
C6—C5—C4—C3	82.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.88	2.10	2.936 (2)	159
N1—H1B···O1ii	0.88	2.09	2.8788 (19)	148
N2—H2···O1ii	0.863 (18)	2.127 (19)	2.9240 (19)	153.2 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	2.10	2.936 (2)	159
N1—H1B⋯O1ii	0.88	2.09	2.8788 (19)	148
N2—H2⋯O1ii	0.863 (18)	2.127 (19)	2.9240 (19)	153.2 (17)

Symmetry codes: (i) ; (ii) .