1,3-Bis(1H-benzimidazol-2-yl)-2-oxapropane.

The title molecule, C(16)H(14)N(4)O, lies on a crystallographic inversion center. The -CH(2)- groups and the O atom are disordered over two sites with equal occupancy, the disorder of the O atom being symmetry imposed. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to (001) via inter-molecular N-H⋯N hydrogen bonds.

Related literature

For the applications of bis­(2-benzimidazol­yl)alkanes, see: Cai et al. (2003 ▶); Min & Suh (2000 ▶); Roderick et al. (1972 ▶). For the isostructural amine analog, see: Tarazon Navarro & McKee (2003 ▶).

Experimental

Crystal data

C16H14N4O

M = 278.31

Orthorhombic,

a = 8.2143 (4) Å

b = 9.6296 (3) Å

c = 16.8088 (7) Å

V = 1329.58 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.19 × 0.13 × 0.09 mm

Data collection

Rigaku R-AXIS Spider diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.983, T max = 0.992

11836 measured reflections

1525 independent reflections

1189 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.112

S = 1.08

1525 reflections

108 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011507/lh2795sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011507/lh2795Isup2.hkl

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

C16H14N4O	F(000) = 584
Mr = 278.31	Dx = 1.390 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1231 reflections
a = 8.2143 (4) Å	θ = 3.5–25.5°
b = 9.6296 (3) Å	µ = 0.09 mm−1
c = 16.8088 (7) Å	T = 153 K
V = 1329.58 (9) Å3	Prism, colourless
Z = 4	0.19 × 0.13 × 0.09 mm

Rigaku R-AXIS Spider diffractometer	1525 independent reflections
Radiation source: fine-focus sealed tube	1189 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.983, Tmax = 0.992	k = −12→11
11836 measured reflections	l = −20→21

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.3224P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1525 reflections	Δρmax = 0.22 e Å−3
108 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.9632 (3)	0.5599 (2)	0.53873 (12)	0.0332 (5)	0.50
N1	0.64853 (14)	0.36549 (11)	0.43694 (6)	0.0256 (3)
N2	0.71007 (14)	0.59185 (11)	0.43361 (7)	0.0254 (3)
H2N	0.770 (2)	0.675 (2)	0.4419 (10)	0.049 (5)*
C1	0.54372 (16)	0.43254 (13)	0.38456 (8)	0.0245 (3)
C2	0.41904 (18)	0.37997 (14)	0.33731 (9)	0.0329 (4)
H2A	0.3907	0.2844	0.3391	0.039*
C3	0.3378 (2)	0.47100 (16)	0.28783 (10)	0.0391 (4)
H3A	0.2525	0.4372	0.2549	0.047*
C4	0.3787 (2)	0.61227 (16)	0.28509 (9)	0.0366 (4)
H4A	0.3217	0.6717	0.2496	0.044*
C5	0.49977 (17)	0.66712 (14)	0.33267 (8)	0.0303 (3)
H5A	0.5257	0.7633	0.3319	0.036*
C6	0.58166 (16)	0.57462 (13)	0.38169 (7)	0.0237 (3)
C7	0.74397 (17)	0.46457 (12)	0.46425 (8)	0.0254 (3)
C8	0.8957 (12)	0.4403 (12)	0.5122 (5)	0.0319 (12)	0.50
H8A	0.8872	0.3484	0.5339	0.038*	0.50
H8B	0.9052	0.5059	0.5549	0.038*	0.50
C8*	0.8603 (12)	0.4441 (12)	0.5307 (5)	0.0319 (12)	0.50
H8*A	0.8049	0.4226	0.5795	0.038*	0.50
H8*B	0.9273	0.3657	0.5177	0.038*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0271 (11)	0.0310 (10)	0.0415 (11)	−0.0002 (8)	−0.0057 (9)	−0.0077 (8)
N1	0.0253 (6)	0.0221 (6)	0.0293 (6)	0.0006 (4)	0.0002 (5)	0.0014 (4)
N2	0.0249 (6)	0.0218 (6)	0.0297 (6)	−0.0011 (5)	−0.0015 (5)	0.0011 (4)
C1	0.0220 (7)	0.0231 (7)	0.0283 (7)	0.0009 (5)	0.0033 (5)	0.0007 (5)
C2	0.0314 (8)	0.0266 (7)	0.0406 (8)	−0.0031 (6)	−0.0052 (6)	−0.0021 (6)
C3	0.0342 (9)	0.0363 (8)	0.0469 (9)	−0.0002 (6)	−0.0148 (7)	−0.0009 (6)
C4	0.0346 (8)	0.0344 (8)	0.0407 (8)	0.0067 (6)	−0.0091 (7)	0.0039 (6)
C5	0.0312 (8)	0.0225 (7)	0.0372 (7)	0.0037 (5)	−0.0002 (6)	0.0016 (5)
C6	0.0208 (7)	0.0230 (6)	0.0273 (6)	0.0008 (5)	0.0010 (5)	−0.0009 (5)
C7	0.0262 (7)	0.0221 (7)	0.0279 (6)	0.0010 (5)	−0.0001 (5)	0.0012 (5)
C8	0.029 (4)	0.0320 (9)	0.034 (4)	−0.001 (2)	−0.004 (2)	0.002 (2)
C8*	0.029 (4)	0.0320 (9)	0.034 (4)	−0.001 (2)	−0.004 (2)	0.002 (2)

O1—C8*	1.405 (12)	C4—C5	1.381 (2)
O1—C8i	1.441 (7)	C4—H4A	0.9500
N1—C7	1.3175 (17)	C5—C6	1.3874 (18)
N1—C1	1.3904 (17)	C5—H5A	0.9500
N2—C7	1.3583 (16)	C7—C8*	1.483 (12)
N2—C6	1.3790 (17)	C7—C8	1.502 (12)
N2—H2N	0.953 (19)	C8—O1i	1.441 (7)
C1—C2	1.3914 (19)	C8—H8A	0.9600
C1—C6	1.4041 (19)	C8—H8B	0.9600
C2—C3	1.380 (2)	C8*—O1i	1.862 (7)
C2—H2A	0.9500	C8*—H8*A	0.9600
C3—C4	1.402 (2)	C8*—H8*B	0.9600
C3—H3A	0.9500
C8—O1—C8i	97.6 (5)	N1—C7—C8	124.6 (5)
C8*—O1—C8i	115.2 (7)	N2—C7—C8	120.9 (5)
C8—O1—C8*i	95.4 (5)	O1—C8—C7	112.6 (8)
C8*—O1—C8*i	113.1 (3)	O1i—C8—C7	110.5 (6)
C8i—O1—H8B	136.0	O1—C8—H8A	133.4
C8*i—O1—H8B	134.6	O1i—C8—H8A	106.5
C7—N1—C1	104.64 (10)	C7—C8—H8A	106.7
C7—N2—C6	106.76 (11)	O1i—C8—H8B	112.3
C7—N2—H2N	126.8 (11)	C7—C8—H8B	111.5
C6—N2—H2N	126.2 (11)	H8A—C8—H8B	109.1
N1—C1—C2	130.41 (12)	O1—C8—H8*A	93.2
N1—C1—C6	109.68 (12)	O1i—C8—H8*A	158.6
C2—C1—C6	119.88 (12)	C7—C8—H8*A	90.6
C3—C2—C1	117.95 (13)	H8A—C8—H8*A	62.0
C3—C2—H2A	121.0	H8B—C8—H8*A	60.4
C1—C2—H2A	121.0	O1—C8—H8*B	128.0
C2—C3—C4	121.35 (14)	O1i—C8—H8*B	78.4
C2—C3—H3A	119.3	C7—C8—H8*B	119.4
C4—C3—H3A	119.3	H8B—C8—H8*B	119.7
C5—C4—C3	121.63 (14)	O1—C8*—C7	110.8 (7)
C5—C4—H4A	119.2	O1—C8*—H8A	128.6
C3—C4—H4A	119.2	C7—C8*—H8A	108.8
C4—C5—C6	116.58 (13)	H8A—C8*—H8B	125.3
C4—C5—H5A	121.7	O1—C8*—H8*A	111.9
C6—C5—H5A	121.7	C7—C8*—H8*A	111.5
N2—C6—C5	132.03 (12)	O1i—C8*—H8*A	154.1
N2—C6—C1	105.38 (11)	O1—C8*—H8*B	107.5
C5—C6—C1	122.58 (13)	C7—C8*—H8*B	107.6
N1—C7—N2	113.54 (12)	H8B—C8*—H8*B	115.5
N1—C7—C8*	123.3 (5)	H8*A—C8*—H8*B	107.3
N2—C7—C8*	122.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1ii	0.953 (19)	1.951 (19)	2.8803 (16)	164.2 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N1i	0.953 (19)	1.951 (19)	2.8803 (16)	164.2 (15)

Symmetry code: (i) .