4-(2-Furylmethyl­ene)-2-(4-morpholino)-1-phenyl-1H-imidazol-4(5H)-one

In the title compound, C₁₈H₁₇N₃O₃, the packing of the mol­ecules in the crystal structure is mainly due to π–π and inter­molecular C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.099
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               1970
           Count of symmetry unique reflns         1988
           Completeness (_total/calc)             99.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Imidazolinones derivatives are of great importance because of their remarkable biological properties (Kiec-Kononowicz et al., 1998). In recent years, we have been engaged in the preparation of heterocyclic derivatives via the aza-Wittig reaction (Hu et al., 2004). The title compound, (I), may be used as a new precursor for obtaining bioactive molecules. The crystal structure of (I) is presented here.

Fig. 1 shows the molecular structure of (I), with the atomic numbering scheme. Selected bond lengths and angles are listed in Table 1. In the crystal structure, there are some weak intermolecular C—H···O hydrogen-bonding interactions and intermolecular π–π interactions (Fig. 2).

S2. Experimental

To a solution of iminophosphorane (1.32 g, 3 mmol) in dry dichloromethane (15 ml) was added phenyl isocyanate (3 mmol) under nitrogen at room temperature. After the reaction mixture was stood for 10 h at room temperature, the solvent was removed under reduced pressure and ether/petroleum ether (1:2, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration the solvent was removed to give carbodiimide (II), which was used directly without further purification. To the solution of (II) prepared above in dichloromethane (15 ml) was added morphiline (3 mmol). After the reaction mixture was allowed to stand for 6 h, the solution was concentrated under reduced pressure and the residue was recrystallized from dichloromethane / petroleum ether (1:4) to give the title compound (I) in yield of 85% (m.p. 491 K). Suitable crystals were obtained by vapor diffusion of ethanol and dichloromethane at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 200 MHz) 3.33 (t, 4H, NCH₂, J = 4.4 Hz), 3.64 (t, 4H, OCH₂, J = 4.9 Hz), 6.80 (s, 1H, =CH), 6.51–7.49 (m, 8H, Ar—H). MS (EI 70 eV) m/z (%): 323 (M⁺, 100), 266 (17), 189 (30), 77 (77). Elemental analysis: calculated for C₁₈H₁₇N₃O₃: C 66.86, H 5.30, N 13.00%; found: C 66.71, H 5.42, N 13.05%.

S3. Refinement

H atoms were placed at calculated positions and treated as riding atoms (C—H in the range 0.93–0.98 Å), with U_iso(H) = 1.2 (CH) or 1.5 (CH₃) times U_eq(parent atom). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size.
	Fig. 2. Packing diagram of (I), showing hydrogen-bonding associations (dashed lines) and the π–π stacking interactions.

4-(2-Furylmethylene)-2-(4-morpholino)-1-phenyl-1H-imidazol-4(5H)-one

Crystal data

C18H17N3O3	F(000) = 340
Mr = 323.35	Dx = 1.332 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2460 reflections
a = 5.5926 (12) Å	θ = 2.5–24.9°
b = 8.8449 (19) Å	µ = 0.09 mm^−1
c = 16.442 (4) Å	T = 292 K
β = 97.536 (3)°	Block, yellow
V = 806.3 (3) Å^3	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1705 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
ϕ and ω scans	h = −7→7
5883 measured reflections	k = −11→11
1970 independent reflections	l = −20→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.051P)^2] where P = (Fo^2 + 2Fc^2)/3
1970 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.2985 (5)	0.6485 (4)	0.01926 (16)	0.0565 (7)
H1	1.4335	0.6799	−0.0037	0.068*
C2	1.1596 (5)	0.5311 (4)	−0.00729 (16)	0.0598 (7)
H2	1.1780	0.4686	−0.0515	0.072*
C3	0.9796 (5)	0.5209 (4)	0.04486 (15)	0.0525 (6)
H3	0.8572	0.4491	0.0419	0.063*
C4	1.0180 (4)	0.6347 (3)	0.10002 (13)	0.0393 (5)
C5	0.9025 (4)	0.6865 (3)	0.16757 (13)	0.0382 (5)
H5	0.9514	0.7795	0.1903	0.046*
C6	0.7295 (4)	0.6122 (2)	0.20101 (13)	0.0347 (5)
C7	0.6272 (4)	0.6664 (2)	0.27454 (13)	0.0363 (5)
C8	0.4854 (4)	0.4384 (2)	0.23077 (13)	0.0344 (5)
C9	0.3839 (4)	0.5365 (3)	0.36866 (13)	0.0371 (5)
C10	0.2014 (4)	0.6297 (3)	0.38680 (15)	0.0448 (5)
H10	0.1359	0.7016	0.3491	0.054*
C11	0.1159 (5)	0.6155 (4)	0.46190 (17)	0.0600 (7)
H11	−0.0086	0.6774	0.4745	0.072*
C12	0.2154 (6)	0.5098 (4)	0.51763 (17)	0.0654 (8)
H12	0.1558	0.4992	0.5675	0.079*
C13	0.3996 (6)	0.4208 (4)	0.50041 (17)	0.0668 (8)
H13	0.4679	0.3512	0.5390	0.080*
C14	0.4871 (5)	0.4330 (3)	0.42535 (15)	0.0527 (6)
H14	0.6136	0.3721	0.4135	0.063*
C15	0.1306 (5)	0.2857 (3)	0.25833 (19)	0.0541 (7)
H15A	0.0069	0.3114	0.2135	0.065*
H15B	0.1141	0.3527	0.3040	0.065*
C16	0.1006 (7)	0.1246 (4)	0.2837 (2)	0.0732 (10)
H16A	0.2186	0.1020	0.3308	0.088*
H16B	−0.0586	0.1117	0.3000	0.088*
C17	0.4063 (5)	0.1962 (3)	0.16698 (17)	0.0531 (7)
H17A	0.5698	0.2046	0.1538	0.064*
H17B	0.2959	0.2187	0.1179	0.064*
C18	0.3623 (6)	0.0389 (3)	0.1956 (2)	0.0724 (9)
H18A	0.3794	−0.0319	0.1517	0.087*
H18B	0.4831	0.0140	0.2415	0.087*
N1	0.6287 (3)	0.4719 (2)	0.17728 (11)	0.0360 (4)
N2	0.4715 (3)	0.5496 (2)	0.29096 (11)	0.0375 (4)
N3	0.3696 (4)	0.3041 (2)	0.23243 (13)	0.0412 (5)
O1	1.2157 (3)	0.7155 (2)	0.08430 (11)	0.0491 (4)
O2	0.6680 (3)	0.77927 (18)	0.31536 (10)	0.0488 (4)
O3	0.1295 (4)	0.0226 (3)	0.21994 (14)	0.0769 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0602 (15)	0.0685 (19)	0.0458 (14)	−0.0007 (14)	0.0257 (12)	0.0032 (13)
C2	0.0722 (17)	0.0673 (19)	0.0421 (14)	−0.0020 (16)	0.0158 (12)	−0.0088 (14)
C3	0.0633 (15)	0.0531 (15)	0.0427 (13)	−0.0132 (13)	0.0126 (11)	−0.0122 (12)
C4	0.0467 (12)	0.0381 (13)	0.0335 (12)	−0.0063 (9)	0.0070 (9)	0.0050 (9)
C5	0.0507 (12)	0.0300 (11)	0.0340 (11)	−0.0071 (9)	0.0063 (9)	−0.0020 (9)
C6	0.0433 (11)	0.0304 (11)	0.0307 (10)	−0.0018 (9)	0.0061 (8)	0.0003 (9)
C7	0.0449 (12)	0.0283 (11)	0.0360 (11)	−0.0001 (8)	0.0064 (9)	0.0019 (9)
C8	0.0407 (11)	0.0290 (10)	0.0340 (11)	0.0031 (9)	0.0067 (8)	0.0006 (9)
C9	0.0395 (11)	0.0402 (12)	0.0331 (11)	−0.0031 (10)	0.0100 (8)	−0.0001 (10)
C10	0.0474 (12)	0.0434 (13)	0.0443 (13)	0.0029 (10)	0.0088 (10)	−0.0037 (11)
C11	0.0600 (15)	0.0634 (19)	0.0623 (18)	0.0033 (14)	0.0289 (13)	−0.0120 (15)
C12	0.089 (2)	0.073 (2)	0.0405 (13)	−0.0076 (17)	0.0288 (14)	0.0016 (15)
C13	0.084 (2)	0.073 (2)	0.0460 (14)	0.0101 (17)	0.0188 (14)	0.0209 (15)
C14	0.0562 (14)	0.0549 (16)	0.0495 (14)	0.0109 (13)	0.0161 (11)	0.0120 (13)
C15	0.0492 (14)	0.0556 (16)	0.0600 (16)	−0.0150 (12)	0.0169 (12)	−0.0096 (13)
C16	0.089 (2)	0.072 (2)	0.0620 (19)	−0.0421 (18)	0.0219 (16)	0.0006 (17)
C17	0.0648 (16)	0.0406 (14)	0.0575 (15)	−0.0129 (12)	0.0213 (13)	−0.0131 (12)
C18	0.086 (2)	0.0385 (15)	0.094 (2)	−0.0151 (15)	0.0140 (18)	−0.0108 (17)
N1	0.0433 (10)	0.0320 (10)	0.0339 (9)	−0.0077 (8)	0.0099 (8)	−0.0033 (8)
N2	0.0488 (10)	0.0323 (9)	0.0333 (10)	−0.0031 (8)	0.0130 (8)	−0.0025 (8)
N3	0.0472 (11)	0.0343 (11)	0.0443 (11)	−0.0092 (8)	0.0141 (8)	−0.0032 (8)
O1	0.0556 (10)	0.0481 (10)	0.0473 (10)	−0.0119 (8)	0.0206 (8)	−0.0013 (8)
O2	0.0689 (11)	0.0335 (9)	0.0459 (9)	−0.0060 (8)	0.0150 (8)	−0.0085 (8)
O3	0.0944 (15)	0.0521 (13)	0.0864 (15)	−0.0406 (12)	0.0202 (12)	−0.0074 (12)

Geometric parameters (Å, º)

C1—C2	1.335 (5)	C10—H10	0.9300
C1—O1	1.356 (3)	C11—C12	1.375 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.408 (4)	C12—C13	1.356 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.353 (4)	C13—C14	1.390 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—O1	1.369 (3)	C14—H14	0.9300
C4—C5	1.431 (3)	C15—N3	1.464 (3)
C5—C6	1.345 (3)	C15—C16	1.500 (5)
C5—H5	0.9300	C15—H15A	0.9700
C6—N1	1.397 (3)	C15—H15B	0.9700
C6—C7	1.484 (3)	C16—O3	1.408 (4)
C7—O2	1.208 (3)	C16—H16A	0.9700
C7—N2	1.401 (3)	C16—H16B	0.9700
C8—N1	1.299 (3)	C17—N3	1.473 (3)
C8—N3	1.355 (3)	C17—C18	1.499 (4)
C8—N2	1.404 (3)	C17—H17A	0.9700
C9—C10	1.375 (3)	C17—H17B	0.9700
C9—C14	1.378 (3)	C18—O3	1.419 (4)
C9—N2	1.431 (3)	C18—H18A	0.9700
C10—C11	1.387 (3)	C18—H18B	0.9700
C2—C1—O1	110.7 (2)	C14—C13—H13	119.8
C2—C1—H1	124.7	C9—C14—C13	119.2 (3)
O1—C1—H1	124.7	C9—C14—H14	120.4
C1—C2—C3	106.4 (3)	C13—C14—H14	120.4
C1—C2—H2	126.8	N3—C15—C16	109.0 (3)
C3—C2—H2	126.8	N3—C15—H15A	109.9
C4—C3—C2	107.3 (2)	C16—C15—H15A	109.9
C4—C3—H3	126.4	N3—C15—H15B	109.9
C2—C3—H3	126.4	C16—C15—H15B	109.9
C3—C4—O1	108.8 (2)	H15A—C15—H15B	108.3
C3—C4—C5	135.3 (2)	O3—C16—C15	111.9 (2)
O1—C4—C5	115.91 (19)	O3—C16—H16A	109.2
C6—C5—C4	125.6 (2)	C15—C16—H16A	109.2
C6—C5—H5	117.2	O3—C16—H16B	109.2
C4—C5—H5	117.2	C15—C16—H16B	109.2
C5—C6—N1	127.2 (2)	H16A—C16—H16B	107.9
C5—C6—C7	123.4 (2)	N3—C17—C18	109.1 (2)
N1—C6—C7	109.29 (18)	N3—C17—H17A	109.9
O2—C7—N2	125.4 (2)	C18—C17—H17A	109.9
O2—C7—C6	130.9 (2)	N3—C17—H17B	109.9
N2—C7—C6	103.55 (19)	C18—C17—H17B	109.9
N1—C8—N3	123.5 (2)	H17A—C17—H17B	108.3
N1—C8—N2	114.43 (19)	O3—C18—C17	112.1 (3)
N3—C8—N2	121.91 (19)	O3—C18—H18A	109.2
C10—C9—C14	120.5 (2)	C17—C18—H18A	109.2
C10—C9—N2	119.7 (2)	O3—C18—H18B	109.2
C14—C9—N2	119.7 (2)	C17—C18—H18B	109.2
C9—C10—C11	119.4 (2)	H18A—C18—H18B	107.9
C9—C10—H10	120.3	C8—N1—C6	105.99 (18)
C11—C10—H10	120.3	C7—N2—C8	106.70 (17)
C12—C11—C10	119.9 (3)	C7—N2—C9	121.71 (18)
C12—C11—H11	120.1	C8—N2—C9	129.03 (19)
C10—C11—H11	120.1	C8—N3—C15	124.1 (2)
C13—C12—C11	120.5 (3)	C8—N3—C17	116.15 (19)
C13—C12—H12	119.7	C15—N3—C17	111.1 (2)
C11—C12—H12	119.7	C1—O1—C4	106.8 (2)
C12—C13—C14	120.4 (3)	C16—O3—C18	110.1 (2)
C12—C13—H13	119.8
O1—C1—C2—C3	−1.1 (3)	O2—C7—N2—C8	−177.4 (2)
C1—C2—C3—C4	0.7 (3)	C6—C7—N2—C8	−0.2 (2)
C2—C3—C4—O1	−0.1 (3)	O2—C7—N2—C9	−14.1 (3)
C2—C3—C4—C5	179.7 (3)	C6—C7—N2—C9	163.18 (18)
C3—C4—C5—C6	10.4 (4)	N1—C8—N2—C7	−1.0 (2)
O1—C4—C5—C6	−169.7 (2)	N3—C8—N2—C7	175.0 (2)
C4—C5—C6—N1	0.1 (4)	N1—C8—N2—C9	−162.7 (2)
C4—C5—C6—C7	175.9 (2)	N3—C8—N2—C9	13.3 (3)
C5—C6—C7—O2	1.8 (4)	C10—C9—N2—C7	77.2 (3)
N1—C6—C7—O2	178.2 (2)	C14—C9—N2—C7	−101.3 (3)
C5—C6—C7—N2	−175.2 (2)	C10—C9—N2—C8	−123.4 (3)
N1—C6—C7—N2	1.2 (2)	C14—C9—N2—C8	58.0 (3)
C14—C9—C10—C11	−2.1 (4)	N1—C8—N3—C15	−147.2 (2)
N2—C9—C10—C11	179.4 (2)	N2—C8—N3—C15	37.1 (3)
C9—C10—C11—C12	0.6 (4)	N1—C8—N3—C17	−2.4 (3)
C10—C11—C12—C13	1.1 (5)	N2—C8—N3—C17	−178.1 (2)
C11—C12—C13—C14	−1.4 (5)	C16—C15—N3—C8	−158.1 (2)
C10—C9—C14—C13	1.9 (4)	C16—C15—N3—C17	55.6 (3)
N2—C9—C14—C13	−179.6 (3)	C18—C17—N3—C8	155.8 (2)
C12—C13—C14—C9	−0.1 (5)	C18—C17—N3—C15	−54.9 (3)
N3—C15—C16—O3	−58.0 (3)	C2—C1—O1—C4	1.0 (3)
N3—C17—C18—O3	56.3 (3)	C3—C4—O1—C1	−0.5 (3)
N3—C8—N1—C6	−174.2 (2)	C5—C4—O1—C1	179.6 (2)
N2—C8—N1—C6	1.8 (2)	C15—C16—O3—C18	59.4 (4)
C5—C6—N1—C8	174.5 (2)	C17—C18—O3—C16	−58.8 (4)
C7—C6—N1—C8	−1.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O2^i	0.97	2.55	3.345 (4)	139
C15—H15A···N1^ii	0.97	2.55	3.374 (4)	143
C5—H5···O3^iii	0.93	2.39	3.303 (3)	166

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z; (iii) x+1, y+1, z.