1,1'-(Propane-1,3-di-yl)bis-(3-phenyl-urea).

The title compound, C(17)H(20)N(4)O(2), has crystallographic inversion symmetry. In the crystal structure, inter-molecular hydrogen bonding between adjacent urea groups gives rise to infinite polymeric chains diagonally across the bc plane. With a centroid-centroid distance of 3.295 (2) Å, π-π stacking is present in the crystal along the same plane.

Related literature

For applications of ureas, see: Park et al. (2011 ▶); Ahmed et al. (2011 ▶); Sharma et al. (2010 ▶); Vos et al. (2010 ▶); Dawn et al. (2011 ▶). For related structures, see: Koevoets et al. (2005 ▶).

Experimental

Crystal data

C17H20N4O2

M = 312.37

Monoclinic,

a = 33.811 (7) Å

b = 4.598 (1) Å

c = 9.891 (2) Å

β = 98.957 (4)°

V = 1518.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.50 × 0.21 × 0.02 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 2007 ▶)T min = 0.955, T max = 0.998

1930 measured reflections

1930 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.05

1930 reflections

114 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035343/hg5067sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035343/hg5067Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035343/hg5067Isup3.cml

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

C17H20N4O2	F(000) = 664
Mr = 312.37	Dx = 1.366 Mg m−3
Monoclinic, C2/c	Melting point: 504 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 33.811 (7) Å	Cell parameters from 1930 reflections
b = 4.598 (1) Å	θ = 2.4–28.5°
c = 9.891 (2) Å	µ = 0.09 mm−1
β = 98.957 (4)°	T = 173 K
V = 1518.9 (6) Å3	Plate, colourless
Z = 4	0.50 × 0.21 × 0.02 mm

Bruker Kappa DUO APEXII diffractometer	1930 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
graphite	Rint = 0.042
0.5° φ scans and ω scans	θmax = 28.5°, θmin = 2.4°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2007)	h = −44→44
Tmin = 0.955, Tmax = 0.998	k = 0→6
1930 measured reflections	l = 0→13

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 = 1.05	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.4485P] where P = (Fo2 + 2Fc2)/3
1930 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.19 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	Occ. (<1)
O1	0.42150 (2)	0.94129 (16)	0.45600 (10)	0.0258 (2)
N1	0.39232 (3)	0.5132 (2)	0.37683 (12)	0.0243 (2)
H1N	0.3915 (4)	0.335 (4)	0.3917 (18)	0.035 (4)*
N2	0.44667 (3)	0.5183 (2)	0.54828 (11)	0.0228 (2)
H2N	0.4448 (5)	0.331 (4)	0.5513 (17)	0.039 (5)*
C1	0.36029 (3)	0.6418 (2)	0.28699 (11)	0.0204 (2)
C2	0.36739 (3)	0.8527 (3)	0.19350 (13)	0.0243 (2)
H2	0.3940	0.9150	0.1897	0.029*
C3	0.33567 (4)	0.9726 (3)	0.10557 (14)	0.0285 (3)
H3	0.3405	1.1188	0.0423	0.034*
C4	0.29688 (4)	0.8801 (3)	0.10954 (14)	0.0297 (3)
H4	0.2752	0.9631	0.0494	0.036*
C5	0.28992 (4)	0.6679 (3)	0.20069 (14)	0.0303 (3)
H5	0.2633	0.6025	0.2023	0.036*
C6	0.32140 (4)	0.5478 (3)	0.29065 (14)	0.0267 (3)
H6	0.3164	0.4026	0.3541	0.032*
C7	0.42011 (3)	0.6716 (2)	0.46010 (12)	0.0194 (2)
C8	0.47434 (3)	0.6748 (2)	0.64875 (13)	0.0247 (3)
H8A	0.4590	0.8079	0.6998	0.030*
H8B	0.4921	0.7951	0.6007	0.030*
C9	0.5000	0.4779 (3)	0.7500	0.0195 (3)
H9B	0.4829	0.3523	0.7980	0.023*	0.50
H9A	0.5171	0.3523	0.7020	0.023*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0313 (4)	0.0117 (4)	0.0306 (4)	0.0004 (3)	−0.0070 (4)	−0.0002 (3)
N1	0.0283 (4)	0.0126 (4)	0.0281 (5)	−0.0010 (4)	−0.0078 (4)	0.0011 (4)
N2	0.0262 (4)	0.0130 (4)	0.0260 (5)	−0.0007 (3)	−0.0057 (4)	0.0003 (4)
C1	0.0240 (5)	0.0158 (5)	0.0195 (5)	0.0011 (4)	−0.0025 (4)	−0.0027 (4)
C2	0.0259 (5)	0.0235 (5)	0.0228 (6)	−0.0003 (4)	0.0018 (4)	0.0003 (5)
C3	0.0366 (6)	0.0261 (6)	0.0215 (5)	0.0016 (5)	0.0008 (5)	0.0045 (5)
C4	0.0295 (6)	0.0282 (6)	0.0277 (6)	0.0056 (5)	−0.0073 (5)	−0.0024 (5)
C5	0.0239 (5)	0.0311 (6)	0.0343 (7)	−0.0022 (4)	−0.0010 (5)	−0.0025 (5)
C6	0.0291 (5)	0.0237 (5)	0.0256 (6)	−0.0042 (4)	−0.0005 (5)	0.0014 (5)
C7	0.0225 (5)	0.0149 (4)	0.0201 (5)	0.0004 (4)	0.0006 (4)	−0.0007 (4)
C8	0.0273 (5)	0.0148 (5)	0.0280 (6)	−0.0005 (4)	−0.0086 (5)	−0.0002 (4)
C9	0.0205 (6)	0.0147 (6)	0.0216 (7)	0.000	−0.0023 (6)	0.000

O1—C7	1.2416 (13)	C3—H3	0.9500
N1—C7	1.3607 (14)	C4—C5	1.373 (2)
N1—C1	1.4187 (14)	C4—H4	0.9500
N1—H1N	0.833 (19)	C5—C6	1.3909 (17)
N2—C7	1.3492 (14)	C5—H5	0.9500
N2—C8	1.4463 (14)	C6—H6	0.9500
N2—H2N	0.862 (19)	C8—C9	1.5180 (14)
C1—C2	1.3866 (17)	C8—H8A	0.9900
C1—C6	1.3898 (17)	C8—H8B	0.9900
C2—C3	1.3857 (16)	C9—C8i	1.5180 (14)
C2—H2	0.9500	C9—H9B	0.9900
C3—C4	1.3850 (19)	C9—H9A	0.9900
C7—N1—C1	122.95 (9)	C6—C5—H5	119.7
C7—N1—H1N	117.3 (11)	C1—C6—C5	119.51 (13)
C1—N1—H1N	118.5 (11)	C1—C6—H6	120.2
C7—N2—C8	118.57 (9)	C5—C6—H6	120.2
C7—N2—H2N	119.8 (11)	O1—C7—N2	121.22 (10)
C8—N2—H2N	121.1 (11)	O1—C7—N1	122.76 (10)
C2—C1—C6	119.85 (11)	N2—C7—N1	116.02 (9)
C2—C1—N1	120.98 (11)	N2—C8—C9	113.49 (9)
C6—C1—N1	119.15 (11)	N2—C8—H8A	108.9
C3—C2—C1	119.95 (11)	C9—C8—H8A	108.9
C3—C2—H2	120.0	N2—C8—H8B	108.9
C1—C2—H2	120.0	C9—C8—H8B	108.9
C4—C3—C2	120.25 (13)	H8A—C8—H8B	107.7
C4—C3—H3	119.9	C8i—C9—C8	106.78 (12)
C2—C3—H3	119.9	C8i—C9—H9B	110.4
C5—C4—C3	119.78 (11)	C8—C9—H9B	110.4
C5—C4—H4	120.1	C8i—C9—H9A	110.4
C3—C4—H4	120.1	C8—C9—H9A	110.4
C4—C5—C6	120.65 (12)	H9B—C9—H9A	108.6
C4—C5—H5	119.7
C7—N1—C1—C2	53.70 (18)	N1—C1—C6—C5	−178.50 (11)
C7—N1—C1—C6	−128.16 (14)	C4—C5—C6—C1	−0.7 (2)
C6—C1—C2—C3	1.05 (18)	C8—N2—C7—O1	6.54 (18)
N1—C1—C2—C3	179.18 (11)	C8—N2—C7—N1	−173.82 (12)
C1—C2—C3—C4	−0.77 (19)	C1—N1—C7—O1	−6.0 (2)
C2—C3—C4—C5	−0.2 (2)	C1—N1—C7—N2	174.39 (12)
C3—C4—C5—C6	1.0 (2)	C7—N2—C8—C9	174.67 (10)
C2—C1—C6—C5	−0.34 (19)	N2—C8—C9—C8i	−177.37 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.834 (18)	2.124 (18)	2.8742 (14)	149.7 (13)
N2—H2N···O1ii	0.864 (18)	2.119 (18)	2.8904 (14)	148.4 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.834 (18)	2.124 (18)	2.8742 (14)	149.7 (13)
N2—H2N⋯O1i	0.864 (18)	2.119 (18)	2.8904 (14)	148.4 (15)

Symmetry code: (i) .