meso-4,5-Diphenyl-imidazolidin-2-one.

The crystal structure determination of the title compound, C(15)H(14)N(2)O, confirms the cis relationship between the phenyl groups at the 4- and 5-positions on the imidazolidine ring. The dihedral angle between the two phenyl rings is 48.14 (6)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into centrosymmetric dimers. These dimers are, in turn, linked into a two-dimensional network via weak N-H⋯π(arene) inter-actions and π-π stacking inter-actions with centroid-centroid distances of 3.6937 (11) Å.

Related literature

For the first synthesis of this compound, see: Biniecki & Moll (1974 ▶). For the synthesis of the trans-isomers, see: Sankhavasi et al. (1991 ▶). For the crystal structure of the (R,R)-isomer, see: Siegler & Long (2006 ▶). For the synthesis of the precursor, see: Proskurnina et al. (2002 ▶). For applications of related enanti­opure compounds, see: Sankhavasi et al. (1991 ▶); Isobe et al. (1998 ▶); Lou et al. (2004 ▶). For potential applications of the title compound, see: Porosa & Viirre (2009 ▶).

Experimental

Crystal data

C15H14N2O

M = 238.28

Triclinic,

a = 6.3539 (4) Å

b = 8.6159 (4) Å

c = 11.3211 (7) Å

α = 86.147 (3)°

β = 76.094 (3)°

γ = 82.718 (3)°

V = 596.32 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.20 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.873, T max = 0.995

6535 measured reflections

2685 independent reflections

1771 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.156

S = 1.03

2685 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046133/sj2668sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046133/sj2668Isup2.hkl

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

C15H14N2O	Z = 2
Mr = 238.28	F(000) = 252
Triclinic, P1	Dx = 1.327 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3539 (4) Å	Cell parameters from 6535 reflections
b = 8.6159 (4) Å	θ = 3.0–27.5°
c = 11.3211 (7) Å	µ = 0.09 mm−1
α = 86.147 (3)°	T = 150 K
β = 76.094 (3)°	Plate, colourless
γ = 82.718 (3)°	0.20 × 0.20 × 0.08 mm
V = 596.32 (6) Å3

Nonius KappaCCD diffractometer	2685 independent reflections
Radiation source: fine-focus sealed tube	1771 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.873, Tmax = 0.995	l = −12→14
6535 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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0787P)2 + 0.1078P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2685 reflections	Δρmax = 0.25 e Å−3
172 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXTL (Version 6.1; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (9)

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	0.5277 (2)	0.41749 (16)	0.65182 (13)	0.0402 (4)
N1	0.2254 (3)	0.55213 (18)	0.59441 (15)	0.0298 (4)
N2	0.2105 (3)	0.50802 (19)	0.79050 (15)	0.0310 (4)
C1	0.0274 (3)	0.6470 (2)	0.65473 (17)	0.0264 (4)
H1A	−0.0938	0.6328	0.6156	0.032*
C2	0.3394 (3)	0.4852 (2)	0.67556 (18)	0.0308 (5)
C3	−0.0134 (3)	0.5630 (2)	0.78442 (17)	0.0283 (5)
H3A	−0.0926	0.4701	0.7831	0.034*
C4	0.0525 (3)	0.8203 (2)	0.65330 (16)	0.0243 (4)
C5	0.2551 (3)	0.8742 (2)	0.63592 (17)	0.0288 (5)
H5A	0.3829	0.8014	0.6267	0.035*
C6	0.2724 (3)	1.0331 (2)	0.63194 (18)	0.0315 (5)
H6A	0.4118	1.0687	0.6195	0.038*
C7	0.0879 (3)	1.1399 (2)	0.64589 (18)	0.0318 (5)
H7A	0.1004	1.2489	0.6430	0.038*
C8	−0.1151 (3)	1.0882 (2)	0.66414 (17)	0.0317 (5)
H8A	−0.2426	1.1614	0.6741	0.038*
C9	−0.1316 (3)	0.9287 (2)	0.66781 (17)	0.0278 (5)
H9A	−0.2713	0.8934	0.6805	0.033*
C10	−0.1371 (3)	0.6618 (2)	0.88918 (16)	0.0259 (4)
C11	−0.0311 (3)	0.7520 (2)	0.94856 (17)	0.0297 (5)
H11A	0.1228	0.7514	0.9233	0.036*
C12	−0.1480 (3)	0.8430 (2)	1.04446 (18)	0.0338 (5)
H12A	−0.0735	0.9030	1.0852	0.041*
C13	−0.3712 (3)	0.8468 (2)	1.08089 (18)	0.0339 (5)
H13A	−0.4510	0.9103	1.1459	0.041*
C14	−0.4787 (3)	0.7580 (2)	1.02265 (19)	0.0364 (5)
H14A	−0.6328	0.7603	1.0479	0.044*
C15	−0.3626 (3)	0.6652 (2)	0.92714 (17)	0.0307 (5)
H15A	−0.4376	0.6039	0.8878	0.037*
H2N	0.248 (3)	0.441 (3)	0.846 (2)	0.035 (6)*
H1N	0.297 (3)	0.569 (2)	0.514 (2)	0.040 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0377 (9)	0.0356 (8)	0.0365 (9)	0.0126 (7)	0.0019 (7)	0.0053 (6)
N1	0.0339 (10)	0.0250 (8)	0.0261 (9)	0.0018 (7)	−0.0011 (7)	−0.0002 (7)
N2	0.0309 (10)	0.0292 (9)	0.0270 (9)	0.0048 (7)	−0.0014 (7)	0.0069 (7)
C1	0.0257 (10)	0.0249 (9)	0.0265 (10)	−0.0011 (8)	−0.0025 (8)	−0.0022 (8)
C2	0.0338 (12)	0.0231 (10)	0.0314 (11)	0.0017 (8)	−0.0030 (9)	0.0025 (8)
C3	0.0265 (10)	0.0236 (9)	0.0324 (10)	−0.0035 (8)	−0.0019 (8)	0.0000 (8)
C4	0.0262 (10)	0.0269 (10)	0.0189 (9)	−0.0010 (8)	−0.0048 (7)	0.0006 (7)
C5	0.0279 (11)	0.0279 (10)	0.0299 (10)	−0.0008 (8)	−0.0070 (8)	0.0013 (8)
C6	0.0328 (11)	0.0335 (11)	0.0296 (11)	−0.0088 (9)	−0.0077 (9)	0.0003 (8)
C7	0.0420 (12)	0.0253 (10)	0.0270 (10)	−0.0048 (9)	−0.0056 (9)	−0.0015 (8)
C8	0.0334 (12)	0.0284 (10)	0.0292 (11)	0.0047 (9)	−0.0041 (9)	0.0001 (8)
C9	0.0245 (10)	0.0302 (10)	0.0275 (10)	−0.0021 (8)	−0.0047 (8)	0.0006 (8)
C10	0.0262 (10)	0.0227 (9)	0.0259 (10)	−0.0024 (8)	−0.0026 (8)	0.0057 (7)
C11	0.0269 (10)	0.0310 (10)	0.0296 (10)	−0.0081 (8)	−0.0017 (8)	0.0013 (8)
C12	0.0444 (13)	0.0292 (10)	0.0277 (11)	−0.0119 (9)	−0.0045 (9)	0.0012 (8)
C13	0.0402 (13)	0.0303 (11)	0.0258 (10)	0.0024 (9)	−0.0009 (9)	0.0001 (8)
C14	0.0262 (11)	0.0460 (13)	0.0326 (11)	0.0013 (9)	−0.0024 (9)	0.0032 (10)
C15	0.0288 (11)	0.0336 (11)	0.0288 (10)	−0.0052 (8)	−0.0047 (8)	−0.0001 (8)

O1—C2	1.238 (2)	C6—H6A	0.9500
N1—C2	1.358 (3)	C7—C8	1.382 (3)
N1—C1	1.456 (2)	C7—H7A	0.9500
N1—H1N	0.93 (2)	C8—C9	1.389 (3)
N2—C2	1.373 (3)	C8—H8A	0.9500
N2—C3	1.458 (3)	C9—H9A	0.9500
N2—H2N	0.87 (2)	C10—C11	1.389 (3)
C1—C4	1.520 (2)	C10—C15	1.391 (3)
C1—C3	1.571 (3)	C11—C12	1.387 (3)
C1—H1A	1.0000	C11—H11A	0.9500
C3—C10	1.506 (3)	C12—C13	1.375 (3)
C3—H3A	1.0000	C12—H12A	0.9500
C4—C9	1.386 (3)	C13—C14	1.380 (3)
C4—C5	1.389 (3)	C13—H13A	0.9500
C5—C6	1.384 (3)	C14—C15	1.392 (3)
C5—H5A	0.9500	C14—H14A	0.9500
C6—C7	1.379 (3)	C15—H15A	0.9500
C2—N1—C1	111.46 (16)	C5—C6—H6A	119.9
C2—N1—H1N	119.9 (13)	C6—C7—C8	119.96 (17)
C1—N1—H1N	123.4 (13)	C6—C7—H7A	120.0
C2—N2—C3	110.27 (16)	C8—C7—H7A	120.0
C2—N2—H2N	113.6 (14)	C7—C8—C9	119.57 (18)
C3—N2—H2N	124.9 (14)	C7—C8—H8A	120.2
N1—C1—C4	113.60 (15)	C9—C8—H8A	120.2
N1—C1—C3	99.73 (14)	C4—C9—C8	121.04 (17)
C4—C1—C3	114.88 (14)	C4—C9—H9A	119.5
N1—C1—H1A	109.4	C8—C9—H9A	119.5
C4—C1—H1A	109.4	C11—C10—C15	118.79 (18)
C3—C1—H1A	109.4	C11—C10—C3	121.43 (17)
O1—C2—N1	126.79 (18)	C15—C10—C3	119.77 (17)
O1—C2—N2	125.27 (18)	C12—C11—C10	120.59 (18)
N1—C2—N2	107.93 (17)	C12—C11—H11A	119.7
N2—C3—C10	113.62 (16)	C10—C11—H11A	119.7
N2—C3—C1	100.24 (14)	C13—C12—C11	120.32 (19)
C10—C3—C1	116.28 (14)	C13—C12—H12A	119.8
N2—C3—H3A	108.8	C11—C12—H12A	119.8
C10—C3—H3A	108.8	C12—C13—C14	119.72 (19)
C1—C3—H3A	108.8	C12—C13—H13A	120.1
C9—C4—C5	118.61 (16)	C14—C13—H13A	120.1
C9—C4—C1	119.26 (16)	C13—C14—C15	120.36 (19)
C5—C4—C1	122.12 (16)	C13—C14—H14A	119.8
C6—C5—C4	120.56 (18)	C15—C14—H14A	119.8
C6—C5—H5A	119.7	C10—C15—C14	120.20 (18)
C4—C5—H5A	119.7	C10—C15—H15A	119.9
C7—C6—C5	120.26 (18)	C14—C15—H15A	119.9
C7—C6—H6A	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.93 (2)	1.94 (2)	2.864 (2)	173 (2)
N2—H2N···Cg1ii	0.87 (2)	2.46 (2)	3.322 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.93 (2)	1.94 (2)	2.864 (2)	173 (2)
N2—H2N⋯Cg1ii	0.87 (2)	2.46 (2)	3.322 (2)	165 (2)

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C4–C9 ring.