1,3-Bis(2-furyl­methyl­idene)-3,4,5,6-tetra­hydro­pyrimidin-2(1H)-one

The title compound, C₁₄H₁₄N₂O₃, possesses C_s symmetry, with the central CH₂ and C=O atoms of the tetra­hydro­pyrimidin-2-one group lying on the mirror plane. The mol­ecule is bow-shaped, with two symmetry-related intramolecular C—H...O hydrogen bonds. In the crystal structure, the mol­ecules stack along the a axis and there are no short intermolecular contacts.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.169
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C5      ..      13.12 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C6      ..       8.75 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C7      ..       9.65 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         N1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C6
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.18 Ratio

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,3-Bis(2-furylmethylidene)-3,4,5,6-tetrahydropyrimidin-2(1H)-one

Crystal data

C14H14N2O3	F(000) = 544
Mr = 258.27	Dx = 1.370 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 812 reflections
a = 7.725 (5) Å	θ = 2.3–18.4°
b = 15.670 (9) Å	µ = 0.10 mm^−1
c = 10.342 (6) Å	T = 298 K
V = 1251.9 (13) Å^3	Block, yellow
Z = 4	0.37 × 0.33 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1151 independent reflections
Radiation source: fine-focus sealed tube	619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.965, Tmax = 0.990	k = −18→14
5987 measured reflections	l = −12→11

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0945P)^2] where P = (Fo^2 + 2Fc^2)/3
1151 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.45 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
O1	0.1189 (3)	0.55038 (14)	0.62677 (19)	0.0705 (8)
O2	0.0260 (4)	0.2500	0.5553 (3)	0.0631 (9)
N1	0.0807 (4)	0.33142 (19)	0.7431 (3)	0.0700 (9)
C1	0.1322 (4)	0.48779 (18)	0.7192 (3)	0.0505 (8)
C2	0.1845 (4)	0.52480 (19)	0.8304 (3)	0.0604 (9)
H2	0.2052	0.4970	0.9084	0.073*
C3	0.2021 (4)	0.6124 (2)	0.8075 (3)	0.0669 (10)
H3	0.2361	0.6537	0.8669	0.080*
C4	0.1607 (5)	0.6249 (2)	0.6849 (3)	0.0747 (11)
H4	0.1604	0.6778	0.6441	0.090*
C5	0.0953 (4)	0.40400 (18)	0.6729 (3)	0.0498 (8)
H5	0.0793	0.3986	0.5841	0.060*
C6	0.0572 (5)	0.2500	0.6721 (4)	0.0458 (10)
C7	0.0948 (4)	0.32988 (18)	0.8888 (3)	0.0518 (8)
H7A	0.2158	0.3340	0.9132	0.062*
H7B	0.0351	0.3791	0.9240	0.062*
C8	0.0188 (5)	0.2500	0.9463 (4)	0.0544 (12)
H8A	0.0391	0.2500	1.0389	0.065*
H8B	−0.1054	0.2500	0.9324	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.111 (2)	0.0512 (14)	0.0488 (14)	−0.0096 (13)	0.0028 (12)	0.0038 (10)
O2	0.090 (2)	0.0562 (19)	0.0433 (18)	0.000	−0.0174 (16)	0.000
N1	0.069 (2)	0.076 (2)	0.0646 (19)	0.0043 (15)	−0.0003 (14)	−0.0030 (15)
C1	0.061 (2)	0.0470 (18)	0.0437 (17)	0.0024 (15)	0.0011 (14)	0.0033 (14)
C2	0.076 (2)	0.052 (2)	0.053 (2)	0.0040 (17)	−0.0060 (17)	0.0000 (15)
C3	0.083 (3)	0.056 (2)	0.062 (2)	−0.0029 (18)	0.0042 (19)	−0.0102 (17)
C4	0.109 (3)	0.048 (2)	0.067 (2)	−0.0127 (19)	0.013 (2)	−0.0002 (18)
C5	0.062 (2)	0.0475 (19)	0.0397 (17)	−0.0019 (14)	−0.0029 (14)	0.0053 (14)
C6	0.052 (3)	0.043 (3)	0.042 (2)	0.000	−0.003 (2)	0.000
C7	0.063 (2)	0.0540 (19)	0.0384 (16)	0.0052 (15)	0.0000 (14)	−0.0033 (13)
C8	0.060 (3)	0.063 (3)	0.041 (2)	0.000	0.002 (2)	0.000

Geometric parameters (Å, º)

O1—C4	1.352 (4)	C3—H3	0.9300
O1—C1	1.374 (3)	C4—H4	0.9300
O2—C6	1.232 (4)	C5—H5	0.9300
N1—C5	1.354 (4)	C6—N1^i	1.483 (4)
N1—C6	1.483 (4)	C7—C8	1.505 (3)
N1—C7	1.511 (4)	C7—H7A	0.9700
C1—C2	1.350 (4)	C7—H7B	0.9700
C1—C5	1.427 (4)	C8—C7^i	1.505 (3)
C2—C3	1.400 (4)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.323 (4)
C4—O1—C1	106.8 (3)	N1—C5—H5	116.2
C5—N1—C6	117.9 (3)	C1—C5—H5	116.2
C5—N1—C7	122.8 (3)	O2—C6—N1	120.61 (18)
C6—N1—C7	119.2 (3)	O2—C6—N1^i	120.61 (18)
C2—C1—O1	108.0 (3)	N1—C6—N1^i	118.7 (4)
C2—C1—C5	137.9 (3)	C8—C7—N1	112.3 (3)
O1—C1—C5	114.1 (3)	C8—C7—H7A	109.1
C1—C2—C3	107.8 (3)	N1—C7—H7A	109.1
C1—C2—H2	126.1	C8—C7—H7B	109.1
C3—C2—H2	126.1	N1—C7—H7B	109.1
C4—C3—C2	106.5 (3)	H7A—C7—H7B	107.9
C4—C3—H3	126.8	C7^i—C8—C7	112.5 (3)
C2—C3—H3	126.8	C7^i—C8—H8A	109.1
C3—C4—O1	110.9 (3)	C7—C8—H8A	109.1
C3—C4—H4	124.6	C7^i—C8—H8B	109.1
O1—C4—H4	124.6	C7—C8—H8B	109.1
N1—C5—C1	127.6 (3)	H8A—C8—H8B	107.8

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.38	2.755 (4)	104