2,4,5-Tri-2-furyl-1H-imidazole.

In the crystal of the title compound, C(15)H(10)N(2)O(3), the molecules are linked together by inter-molecular N-H⋯N hydrogen bonds into chains along the c axis. The crystal structure also shows weak inter-molecular C-H⋯π hydrogen bonds. The three furanyl rings bonded to the imidazole core are not coplanar with the latter; the dihedral angles between the furanyl and imidazole ring planes are 29.3 (2), 19.4 (2), and 4.8 (2)°.

Related literature

For background to imidazole derivatives, see: Ho et al. (2003 ▶); Lambardino et al. (1974 ▶); Bao et al. (2003 ▶); Fürstner et al. (2000 ▶); Sundberg et al. (1996 ▶).

Experimental

Crystal data

C15H10N2O3

M = 266.25

Monoclinic,

a = 9.3940 (19) Å

b = 17.146 (3) Å

c = 9.1484 (18) Å

β = 116.29 (3)°

V = 1321.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.26 × 0.24 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.975, T max = 0.989

6430 measured reflections

1514 independent reflections

1089 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.04

1514 reflections

185 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049514/om2298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049514/om2298Isup2.hkl

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

C15H10N2O3	Z = 4
Mr = 266.25	F(000) = 552
Monoclinic, Cc	Dx = 1.339 Mg m−3
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3940 (19) Å	θ = 3.4–27.5°
b = 17.146 (3) Å	µ = 0.10 mm−1
c = 9.1484 (18) Å	T = 295 K
β = 116.29 (3)°	Block, yellow
V = 1321.1 (5) Å3	0.26 × 0.24 × 0.12 mm

Rigaku R-AXIS RAPID diffractometer	1514 independent reflections
Radiation source: fine-focus sealed tube	1089 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.975, Tmax = 0.989	k = −22→22
6430 measured reflections	l = −11→10

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0752P)2] where P = (Fo2 + 2Fc2)/3
1514 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.13 e Å−3
2 restraints	Δρmin = −0.14 e Å−3

Experimental. (See detailed section in the paper)

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	0.2149 (4)	0.03841 (17)	0.1765 (4)	0.0969 (10)
O2	0.2353 (3)	0.22150 (13)	−0.1681 (3)	0.0785 (7)
O3	0.7630 (4)	−0.05039 (19)	−0.0235 (3)	0.0887 (8)
N1	0.4736 (3)	0.01826 (14)	0.1105 (3)	0.0514 (6)
H1A	0.484 (5)	−0.016 (2)	0.199 (5)	0.071 (10)*
N2	0.5145 (3)	0.06255 (15)	−0.0952 (3)	0.0523 (6)
C1	0.1128 (7)	0.0677 (3)	0.2310 (8)	0.1106 (17)
H1	0.0680	0.0389	0.2862	0.133*
C2	0.0868 (6)	0.1396 (3)	0.1967 (6)	0.0962 (14)
H2	0.0198	0.1716	0.2203	0.115*
C3	0.1802 (6)	0.1624 (3)	0.1147 (5)	0.0918 (13)
H3	0.1872	0.2118	0.0767	0.110*
C4	0.2547 (4)	0.09777 (18)	0.1044 (4)	0.0558 (7)
C5	0.3664 (3)	0.07872 (16)	0.0416 (3)	0.0488 (6)
C6	0.3936 (3)	0.10452 (16)	−0.0868 (3)	0.0499 (7)
C7	0.3183 (3)	0.16580 (17)	−0.2043 (4)	0.0564 (7)
C8	0.3121 (5)	0.1808 (2)	−0.3509 (4)	0.0832 (11)
H8	0.3586	0.1518	−0.4043	0.100*
C9	0.2190 (5)	0.2505 (3)	−0.4089 (6)	0.0884 (13)
H9	0.1935	0.2754	−0.5077	0.106*
C10	0.1770 (5)	0.2724 (2)	−0.2969 (6)	0.0882 (14)
H10	0.1162	0.3162	−0.3035	0.106*
C11	0.5600 (3)	0.01121 (16)	0.0265 (3)	0.0492 (6)
C12	0.6862 (4)	−0.04443 (19)	0.0694 (4)	0.0588 (8)
C13	0.7492 (5)	−0.0938 (2)	0.1934 (5)	0.0807 (12)
H13	0.7166	−0.1013	0.2747	0.097*
C14	0.8742 (5)	−0.1329 (3)	0.1795 (7)	0.0974 (14)
H14	0.9409	−0.1704	0.2501	0.117*
C15	0.8781 (6)	−0.1061 (3)	0.0482 (7)	0.1003 (15)
H15	0.9489	−0.1224	0.0086	0.120*

	U11	U22	U33	U12	U13	U23
O1	0.102 (2)	0.0895 (19)	0.136 (3)	0.0189 (17)	0.085 (2)	0.0234 (17)
O2	0.0788 (15)	0.0619 (14)	0.0816 (15)	0.0195 (13)	0.0236 (12)	0.0141 (12)
O3	0.0850 (18)	0.111 (2)	0.0780 (15)	0.0260 (16)	0.0436 (14)	0.0038 (15)
N1	0.0502 (13)	0.0540 (13)	0.0454 (12)	0.0098 (11)	0.0170 (10)	0.0059 (10)
N2	0.0473 (12)	0.0571 (14)	0.0476 (12)	−0.0017 (12)	0.0165 (10)	−0.0001 (10)
C1	0.104 (4)	0.124 (4)	0.142 (4)	0.027 (3)	0.089 (4)	0.017 (3)
C2	0.084 (3)	0.118 (4)	0.098 (3)	0.045 (3)	0.051 (2)	0.009 (3)
C3	0.108 (3)	0.077 (2)	0.095 (3)	0.029 (2)	0.049 (2)	0.002 (2)
C4	0.0501 (16)	0.0563 (17)	0.0575 (16)	0.0085 (14)	0.0208 (13)	0.0027 (13)
C5	0.0430 (13)	0.0484 (14)	0.0467 (14)	0.0027 (12)	0.0123 (10)	−0.0007 (11)
C6	0.0469 (14)	0.0453 (15)	0.0464 (14)	−0.0003 (12)	0.0107 (11)	−0.0005 (11)
C7	0.0481 (16)	0.0486 (15)	0.0588 (16)	−0.0060 (13)	0.0111 (12)	0.0037 (12)
C8	0.093 (3)	0.079 (2)	0.072 (2)	0.010 (2)	0.032 (2)	0.0216 (19)
C9	0.084 (3)	0.078 (2)	0.079 (2)	0.001 (2)	0.014 (2)	0.035 (2)
C10	0.073 (2)	0.067 (2)	0.096 (3)	0.0108 (19)	0.011 (2)	0.030 (2)
C11	0.0473 (14)	0.0504 (15)	0.0454 (13)	0.0050 (13)	0.0164 (11)	−0.0010 (12)
C12	0.0528 (17)	0.0630 (18)	0.0578 (16)	0.0080 (14)	0.0222 (14)	−0.0051 (14)
C13	0.086 (3)	0.078 (2)	0.087 (2)	0.037 (2)	0.047 (2)	0.026 (2)
C14	0.080 (3)	0.087 (3)	0.111 (3)	0.039 (2)	0.029 (2)	0.016 (3)
C15	0.072 (2)	0.111 (3)	0.117 (4)	0.031 (3)	0.042 (3)	−0.018 (3)

O1—C4	1.352 (4)	C4—C5	1.440 (4)
O1—C1	1.358 (5)	C5—C6	1.381 (4)
O2—C7	1.363 (4)	C6—C7	1.444 (4)
O2—C10	1.370 (4)	C7—C8	1.341 (5)
O3—C12	1.340 (4)	C8—C9	1.437 (6)
O3—C15	1.373 (6)	C8—H8	0.9300
N1—C11	1.349 (4)	C9—C10	1.306 (7)
N1—C5	1.387 (4)	C9—H9	0.9300
N1—H1A	0.96 (4)	C10—H10	0.9300
N2—C11	1.332 (4)	C11—C12	1.434 (4)
N2—C6	1.375 (4)	C12—C13	1.326 (5)
C1—C2	1.269 (7)	C13—C14	1.406 (6)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.438 (7)	C14—C15	1.302 (7)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.336 (5)	C15—H15	0.9300
C3—H3	0.9300
C4—O1—C1	107.1 (3)	C8—C7—C6	132.3 (3)
C7—O2—C10	106.9 (3)	O2—C7—C6	118.2 (3)
C12—O3—C15	106.3 (4)	C7—C8—C9	106.2 (4)
C11—N1—C5	107.9 (2)	C7—C8—H8	126.9
C11—N1—H1A	124 (2)	C9—C8—H8	126.9
C5—N1—H1A	128 (2)	C10—C9—C8	107.2 (3)
C11—N2—C6	105.5 (2)	C10—C9—H9	126.4
C2—C1—O1	111.0 (4)	C8—C9—H9	126.4
C2—C1—H1	124.5	C9—C10—O2	110.3 (4)
O1—C1—H1	124.5	C9—C10—H10	124.8
C1—C2—C3	107.4 (4)	O2—C10—H10	124.8
C1—C2—H2	126.3	N2—C11—N1	111.4 (2)
C3—C2—H2	126.3	N2—C11—C12	126.1 (3)
C4—C3—C2	105.7 (4)	N1—C11—C12	122.5 (2)
C4—C3—H3	127.1	C13—C12—O3	109.4 (3)
C2—C3—H3	127.1	C13—C12—C11	131.3 (3)
C3—C4—O1	108.9 (3)	O3—C12—C11	119.3 (3)
C3—C4—C5	135.5 (3)	C12—C13—C14	107.5 (4)
O1—C4—C5	115.6 (3)	C12—C13—H13	126.2
C6—C5—N1	104.8 (3)	C14—C13—H13	126.2
C6—C5—C4	135.2 (3)	C15—C14—C13	106.3 (4)
N1—C5—C4	119.9 (3)	C15—C14—H14	126.8
N2—C6—C5	110.4 (2)	C13—C14—H14	126.8
N2—C6—C7	118.9 (3)	C14—C15—O3	110.4 (4)
C5—C6—C7	130.7 (3)	C14—C15—H15	124.8
C8—C7—O2	109.4 (3)	O3—C15—H15	124.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.97 (3)	1.94 (3)	2.899 (3)	167 (2)
C10—H10···Cgii	0.93	2.81 (1)	3.6031 (31)	144 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.97 (3)	1.94 (3)	2.899 (3)	167 (2)
C10—H10⋯Cg ii	0.93	2.81	3.6031 (31)	144

Symmetry codes: (i) ; (ii) . Cg is the centroid of the N1/C5/C6/N2/C11 ring.