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

In the title mol-ecule, C(18)H(18)N(4)O, the dihedral angle between the mean planes of the two benzimidazole ring systems is 61.5 (1)°.

Related literature

For biological applications of benzimidazoles and bis-benzimidazoles, see: Horton et al. (2003 ▶); Holland & Tolman (2000 ▶). For related structures, see: Chen et al. (2009 ▶); Wu et al. (2009 ▶).

Experimental

Crystal data

C18H18N4O

M = 306.36

Monoclinic,

a = 6.634 (6) Å

b = 16.217 (15) Å

c = 14.457 (13) Å

β = 101.102 (10)°

V = 1526 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.26 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.982

10239 measured reflections

2668 independent reflections

1846 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.169

S = 1.05

2668 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536811017922/lh5249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017922/lh5249Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017922/lh5249Isup3.cml

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

C18H18N4O	F(000) = 648
Mr = 306.36	Dx = 1.333 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1941 reflections
a = 6.634 (6) Å	θ = 2.5–23.0°
b = 16.217 (15) Å	µ = 0.09 mm−1
c = 14.457 (13) Å	T = 296 K
β = 101.102 (10)°	Block, white
V = 1526 (2) Å3	0.26 × 0.24 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	2668 independent reflections
Radiation source: fine-focus sealed tube	1846 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.978, Tmax = 0.982	k = −17→19
10239 measured reflections	l = −17→17

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.169	w = 1/[σ2(Fo2) + (0.062P)2 + 1.2125P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2668 reflections	Δρmax = 0.19 e Å−3
210 parameters	Δρmin = −0.19 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: 0.0025 (4)

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	0.1874 (3)	0.23663 (13)	0.39791 (14)	0.0471 (6)
N3	0.4241 (4)	0.11107 (15)	0.52270 (17)	0.0410 (6)
N1	0.2920 (4)	0.23299 (15)	0.19655 (17)	0.0439 (6)
C11	0.2170 (4)	0.12133 (18)	0.5023 (2)	0.0407 (7)
N2	−0.0371 (4)	0.19270 (17)	0.16948 (18)	0.0489 (7)
C12	0.2789 (5)	0.05940 (18)	0.6348 (2)	0.0427 (7)
C8	0.2615 (5)	0.18872 (19)	0.1131 (2)	0.0437 (8)
N4	0.1227 (4)	0.09232 (16)	0.56732 (18)	0.0467 (7)
C17	0.4691 (5)	0.07179 (18)	0.6089 (2)	0.0410 (7)
C3	0.0574 (5)	0.1645 (2)	0.0974 (2)	0.0463 (8)
C2	0.1090 (5)	0.23293 (19)	0.2256 (2)	0.0424 (7)
C16	0.6514 (5)	0.0441 (2)	0.6624 (2)	0.0524 (9)
H16	0.7768	0.0531	0.6444	0.063*
C18	0.5751 (5)	0.1358 (2)	0.4666 (2)	0.0505 (8)
H18A	0.5239	0.1228	0.4015	0.076*
H18B	0.7014	0.1067	0.4882	0.076*
H18C	0.5990	0.1940	0.4731	0.076*
C13	0.2710 (6)	0.0182 (2)	0.7183 (2)	0.0553 (9)
H13	0.1466	0.0102	0.7377	0.066*
C10	0.1078 (5)	0.1576 (2)	0.4120 (2)	0.0482 (8)
H10A	0.1235	0.1217	0.3602	0.058*
H10B	−0.0376	0.1620	0.4129	0.058*
C15	0.6381 (6)	0.0023 (2)	0.7440 (2)	0.0610 (10)
H15	0.7574	−0.0179	0.7818	0.073*
C1	0.0810 (5)	0.2749 (2)	0.3144 (2)	0.0494 (8)
H1A	0.1279	0.3315	0.3132	0.059*
H1B	−0.0643	0.2763	0.3162	0.059*
C4	−0.0213 (6)	0.1176 (2)	0.0180 (2)	0.0612 (10)
H4A	−0.1579	0.1007	0.0055	0.073*
C7	0.3946 (6)	0.1688 (2)	0.0531 (2)	0.0550 (9)
H7	0.5310	0.1858	0.0645	0.066*
C5	0.1093 (7)	0.0971 (2)	−0.0410 (2)	0.0675 (11)
H5	0.0601	0.0654	−0.0942	0.081*
C9	0.4856 (5)	0.2688 (2)	0.2415 (3)	0.0614 (10)
H9A	0.4693	0.2959	0.2986	0.092*
H9B	0.5290	0.3082	0.1998	0.092*
H9C	0.5871	0.2261	0.2559	0.092*
C6	0.3114 (7)	0.1222 (2)	−0.0240 (2)	0.0657 (11)
H6	0.3943	0.1070	−0.0662	0.079*
C14	0.4501 (6)	−0.0104 (2)	0.7712 (2)	0.0616 (10)
H14	0.4465	−0.0391	0.8266	0.074*

	U11	U22	U33	U12	U13	U23
O1	0.0496 (12)	0.0464 (13)	0.0446 (12)	−0.0009 (10)	0.0075 (10)	0.0015 (10)
N3	0.0392 (14)	0.0429 (14)	0.0424 (14)	−0.0022 (11)	0.0119 (11)	−0.0009 (11)
N1	0.0427 (15)	0.0459 (15)	0.0439 (15)	−0.0012 (12)	0.0102 (11)	0.0036 (12)
C11	0.0399 (17)	0.0407 (17)	0.0426 (17)	−0.0002 (14)	0.0106 (13)	−0.0045 (14)
N2	0.0466 (16)	0.0534 (17)	0.0468 (15)	0.0040 (13)	0.0090 (12)	0.0063 (13)
C12	0.0520 (19)	0.0372 (17)	0.0407 (17)	0.0057 (14)	0.0134 (14)	−0.0051 (13)
C8	0.053 (2)	0.0408 (18)	0.0398 (17)	0.0079 (15)	0.0153 (14)	0.0134 (14)
N4	0.0443 (15)	0.0505 (16)	0.0479 (15)	0.0059 (12)	0.0151 (12)	0.0048 (12)
C17	0.0447 (17)	0.0352 (17)	0.0423 (17)	0.0015 (14)	0.0063 (13)	−0.0076 (13)
C3	0.0506 (19)	0.0472 (19)	0.0399 (17)	0.0044 (15)	0.0057 (14)	0.0075 (14)
C2	0.0401 (17)	0.0438 (18)	0.0433 (17)	0.0076 (14)	0.0075 (14)	0.0079 (14)
C16	0.0474 (19)	0.048 (2)	0.058 (2)	0.0011 (15)	0.0009 (15)	−0.0067 (16)
C18	0.0440 (18)	0.053 (2)	0.059 (2)	−0.0054 (16)	0.0199 (15)	−0.0034 (16)
C13	0.066 (2)	0.054 (2)	0.050 (2)	0.0105 (17)	0.0214 (17)	0.0032 (16)
C10	0.0456 (18)	0.054 (2)	0.0453 (18)	−0.0070 (16)	0.0084 (14)	0.0050 (15)
C15	0.070 (2)	0.048 (2)	0.057 (2)	0.0137 (18)	−0.0074 (18)	−0.0001 (17)
C1	0.055 (2)	0.0468 (19)	0.0469 (18)	0.0086 (16)	0.0113 (15)	0.0040 (15)
C4	0.072 (2)	0.055 (2)	0.052 (2)	−0.0047 (19)	0.0003 (18)	0.0031 (17)
C7	0.065 (2)	0.052 (2)	0.052 (2)	0.0065 (17)	0.0228 (17)	0.0138 (17)
C5	0.102 (3)	0.059 (2)	0.042 (2)	0.002 (2)	0.014 (2)	−0.0020 (17)
C9	0.051 (2)	0.070 (2)	0.065 (2)	−0.0092 (18)	0.0124 (17)	0.0022 (19)
C6	0.095 (3)	0.060 (2)	0.050 (2)	0.014 (2)	0.032 (2)	0.0097 (18)
C14	0.089 (3)	0.049 (2)	0.0462 (19)	0.014 (2)	0.0103 (19)	0.0023 (16)

O1—C10	1.416 (4)	C18—H18A	0.9600
O1—C1	1.419 (4)	C18—H18B	0.9600
N3—C11	1.359 (4)	C18—H18C	0.9600
N3—C17	1.380 (4)	C13—C14	1.364 (5)
N3—C18	1.461 (4)	C13—H13	0.9300
N1—C2	1.359 (4)	C10—H10A	0.9700
N1—C8	1.385 (4)	C10—H10B	0.9700
N1—C9	1.445 (4)	C15—C14	1.394 (5)
C11—N4	1.313 (4)	C15—H15	0.9300
C11—C10	1.486 (4)	C1—H1A	0.9700
N2—C2	1.311 (4)	C1—H1B	0.9700
N2—C3	1.392 (4)	C4—C5	1.369 (5)
C12—N4	1.386 (4)	C4—H4A	0.9300
C12—C13	1.390 (4)	C7—C6	1.372 (5)
C12—C17	1.398 (4)	C7—H7	0.9300
C8—C3	1.386 (4)	C5—C6	1.377 (5)
C8—C7	1.389 (4)	C5—H5	0.9300
C17—C16	1.380 (4)	C9—H9A	0.9600
C3—C4	1.393 (5)	C9—H9B	0.9600
C2—C1	1.497 (4)	C9—H9C	0.9600
C16—C15	1.378 (5)	C6—H6	0.9300
C16—H16	0.9300	C14—H14	0.9300
C10—O1—C1	112.4 (2)	C12—C13—H13	120.8
C11—N3—C17	106.7 (2)	O1—C10—C11	110.6 (2)
C11—N3—C18	128.2 (3)	O1—C10—H10A	109.5
C17—N3—C18	125.1 (3)	C11—C10—H10A	109.5
C2—N1—C8	106.2 (2)	O1—C10—H10B	109.5
C2—N1—C9	129.1 (3)	C11—C10—H10B	109.5
C8—N1—C9	124.6 (3)	H10A—C10—H10B	108.1
N4—C11—N3	113.7 (3)	C16—C15—C14	121.5 (3)
N4—C11—C10	123.5 (3)	C16—C15—H15	119.2
N3—C11—C10	122.7 (3)	C14—C15—H15	119.2
C2—N2—C3	103.9 (3)	O1—C1—C2	114.0 (3)
N4—C12—C13	130.4 (3)	O1—C1—H1A	108.7
N4—C12—C17	110.3 (3)	C2—C1—H1A	108.7
C13—C12—C17	119.3 (3)	O1—C1—H1B	108.7
N1—C8—C3	105.2 (3)	C2—C1—H1B	108.7
N1—C8—C7	131.3 (3)	H1A—C1—H1B	107.6
C3—C8—C7	123.4 (3)	C5—C4—C3	117.7 (4)
C11—N4—C12	104.3 (3)	C5—C4—H4A	121.2
N3—C17—C16	132.2 (3)	C3—C4—H4A	121.2
N3—C17—C12	105.0 (3)	C6—C7—C8	115.5 (3)
C16—C17—C12	122.8 (3)	C6—C7—H7	122.3
C8—C3—N2	110.6 (3)	C8—C7—H7	122.3
C8—C3—C4	119.2 (3)	C4—C5—C6	121.9 (4)
N2—C3—C4	130.2 (3)	C4—C5—H5	119.0
N2—C2—N1	114.1 (3)	C6—C5—H5	119.0
N2—C2—C1	123.9 (3)	N1—C9—H9A	109.5
N1—C2—C1	122.0 (3)	N1—C9—H9B	109.5
C15—C16—C17	116.6 (3)	H9A—C9—H9B	109.5
C15—C16—H16	121.7	N1—C9—H9C	109.5
C17—C16—H16	121.7	H9A—C9—H9C	109.5
N3—C18—H18A	109.5	H9B—C9—H9C	109.5
N3—C18—H18B	109.5	C7—C6—C5	122.3 (3)
H18A—C18—H18B	109.5	C7—C6—H6	118.9
N3—C18—H18C	109.5	C5—C6—H6	118.9
H18A—C18—H18C	109.5	C13—C14—C15	121.4 (3)
H18B—C18—H18C	109.5	C13—C14—H14	119.3
C14—C13—C12	118.4 (3)	C15—C14—H14	119.3
C14—C13—H13	120.8