2,6-Bis(1H-benzimidazol--2-yl)pyridine methanol trisolvate.

In the title compound, C(19)H(13)N(5)·3CH(4)O, the 2,6-bis-(2-benzimidazol-yl)pyridine mol-ecule is essentially planar with an r.m.s. deviation for all non-H atoms of 0.185 Å. The crystal structure is stabilized by inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds and weak π⋯π stacking inter-actions with centroid-centroid distances of 3.6675 (16) and 3.6891 (15) Å. The atoms of one of the methanol solvent molecules are disordered over two sites with refined occupancies of 0.606(8) and 0.394(8).

Related literature

For the crystal structures of the mono- and sesquihydrate analogs of 2,6-bis­(2-benzimidazol­yl)pyridine, see: Freire et al. (2003 ▶). For the synthesis of 2,6-bis­(2-benzimidazol­yl)pyridine, see: Addison & Burke (1981 ▶).

Experimental

Crystal data

C19H13N5·3CH4O

M = 407.47

Monoclinic,

a = 11.2686 (9) Å

b = 15.0928 (13) Å

c = 13.0679 (11) Å

β = 107.391 (2)°

V = 2120.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.18 × 0.14 × 0.11 mm

Data collection

Rigaku R-AXIS Spider diffractometer

Absorption correction: multi-scan (Higashi, 1995 ▶) T min = 0.984, T max = 0.990

17035 measured reflections

3945 independent reflections

2527 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.236

S = 1.04

3945 reflections

307 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.40 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012574/lh2799sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012574/lh2799Isup2.hkl

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

C19H13N5·3CH4O	F(000) = 864
Mr = 407.47	Dx = 1.276 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3945 reflections
a = 11.2686 (9) Å	θ = 3.2–25.5°
b = 15.0928 (13) Å	µ = 0.09 mm−1
c = 13.0679 (11) Å	T = 153 K
β = 107.391 (2)°	Block, colorless
V = 2120.9 (3) Å3	0.18 × 0.14 × 0.11 mm
Z = 4

Rigaku R-AXIS Spider diffractometer	3945 independent reflections
Radiation source: fine-focus sealed tube	2527 reflections with I > 2σ(I)
graphite	Rint = 0.071
φ and ω scans	θmax = 25.5°, θmin = 3.2°
Absorption correction: multi-scan (Higashi, 1995)	h = −13→11
Tmin = 0.984, Tmax = 0.990	k = −18→18
17035 measured reflections	l = −15→15

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)] = 0.077	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.236	w = 1/[σ2(Fo2) + (0.1505P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
3945 reflections	Δρmax = 0.39 e Å−3
307 parameters	Δρmin = −0.40 e Å−3
2 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (6)

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	Occ. (<1)
O1	0.20534 (18)	0.61337 (13)	0.36351 (15)	0.0631 (6)
H1	0.2509	0.6582	0.3816	0.076*
O2	0.65988 (19)	0.23950 (14)	0.57774 (17)	0.0704 (6)
H2	0.6009	0.2626	0.5299	0.084*
N1	0.11042 (19)	0.58598 (15)	0.54657 (17)	0.0477 (6)
N2	0.0754 (2)	0.53929 (15)	0.69788 (17)	0.0517 (6)
N3	0.3694 (2)	0.46017 (15)	0.38227 (18)	0.0510 (6)
N4	0.4825 (2)	0.33787 (15)	0.43304 (18)	0.0536 (6)
N5	0.27120 (19)	0.45211 (14)	0.54781 (16)	0.0492 (6)
C1	0.0280 (2)	0.64631 (18)	0.5671 (2)	0.0498 (7)
C2	−0.0274 (2)	0.72243 (19)	0.5148 (2)	0.0558 (7)
H2A	−0.0109	0.7432	0.4518	0.067*
C3	−0.1076 (3)	0.7667 (2)	0.5589 (2)	0.0609 (8)
H3	−0.1476	0.8191	0.5254	0.073*
C4	−0.1313 (3)	0.7359 (2)	0.6519 (2)	0.0615 (8)
H4	−0.1875	0.7680	0.6795	0.074*
C5	−0.0761 (2)	0.6613 (2)	0.7043 (2)	0.0558 (7)
H5	−0.0930	0.6411	0.7674	0.067*
C6	0.0060 (2)	0.61602 (18)	0.6613 (2)	0.0500 (7)
C7	0.1350 (2)	0.52423 (17)	0.6263 (2)	0.0479 (6)
C8	0.2211 (2)	0.45155 (17)	0.62863 (19)	0.0467 (7)
C9	0.2477 (2)	0.38735 (18)	0.7084 (2)	0.0513 (7)
H9	0.2096	0.3888	0.7641	0.062*
C10	0.3312 (2)	0.32126 (18)	0.7045 (2)	0.0536 (7)
H10	0.3520	0.2767	0.7582	0.064*
C11	0.3837 (2)	0.32049 (18)	0.6221 (2)	0.0529 (7)
H11	0.4411	0.2755	0.6181	0.063*
C12	0.3512 (2)	0.38721 (17)	0.5444 (2)	0.0471 (7)
C13	0.4022 (2)	0.39322 (17)	0.4542 (2)	0.0480 (7)
C14	0.5051 (2)	0.37188 (19)	0.3421 (2)	0.0539 (7)
C15	0.5848 (3)	0.3422 (2)	0.2854 (2)	0.0656 (8)
H15	0.6334	0.2901	0.3066	0.079*
C16	0.5905 (3)	0.3906 (2)	0.1981 (3)	0.0695 (9)
H16	0.6442	0.3717	0.1584	0.083*
C17	0.5188 (3)	0.4674 (2)	0.1662 (2)	0.0713 (9)
H17	0.5244	0.4990	0.1049	0.086*
C18	0.4406 (3)	0.4980 (2)	0.2211 (2)	0.0616 (8)
H18	0.3930	0.5504	0.1999	0.074*
C19	0.4344 (2)	0.44882 (18)	0.3089 (2)	0.0531 (7)
C20	0.1118 (3)	0.6305 (3)	0.2645 (3)	0.0789 (10)
H20A	0.0453	0.6661	0.2780	0.095*
H20B	0.0773	0.5742	0.2312	0.095*
H20C	0.1484	0.6628	0.2163	0.095*
C21	0.7174 (4)	0.1739 (3)	0.5314 (4)	0.0958 (12)
H21A	0.7639	0.2025	0.4879	0.115*
H21B	0.6536	0.1350	0.4858	0.115*
H21C	0.7745	0.1389	0.5883	0.115*
O3	0.1278 (5)	0.5658 (3)	0.9743 (4)	0.094 (2)	0.606 (8)
H3A	0.1412	0.5425	1.0350	0.112*	0.606 (8)
C22	0.2186 (8)	0.5366 (7)	0.9269 (9)	0.0521 (19)	0.606 (8)
H22A	0.2730	0.5862	0.9227	0.062*	0.606 (8)
H22B	0.1774	0.5142	0.8547	0.062*	0.606 (8)
H22C	0.2681	0.4892	0.9707	0.062*	0.606 (8)
O3'	0.0859 (9)	0.4916 (6)	0.8986 (6)	0.118 (4)	0.394 (8)
H3'	0.0325	0.5092	0.9272	0.141*	0.394 (8)
C22'	0.1816 (12)	0.5468 (13)	0.9232 (18)	0.078 (5)	0.394 (8)
H22D	0.1522	0.6072	0.9022	0.094*	0.394 (8)
H22E	0.2405	0.5293	0.8848	0.094*	0.394 (8)
H22F	0.2230	0.5449	1.0006	0.094*	0.394 (8)
H1N	0.144 (3)	0.589 (2)	0.4954 (17)	0.075 (10)*
H3N	0.316 (3)	0.5018 (17)	0.380 (3)	0.095 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.0689 (13)	0.0565 (13)	0.0638 (13)	0.0040 (9)	0.0197 (10)	0.0078 (9)
O2	0.0655 (13)	0.0665 (14)	0.0811 (15)	0.0113 (10)	0.0249 (11)	0.0109 (11)
N1	0.0473 (12)	0.0518 (13)	0.0463 (12)	0.0027 (10)	0.0175 (10)	0.0002 (10)
N2	0.0524 (12)	0.0558 (14)	0.0479 (12)	−0.0030 (10)	0.0164 (10)	−0.0030 (10)
N3	0.0535 (13)	0.0505 (14)	0.0516 (13)	−0.0013 (10)	0.0196 (10)	−0.0001 (10)
N4	0.0559 (13)	0.0514 (14)	0.0553 (13)	−0.0005 (10)	0.0194 (10)	−0.0041 (10)
N5	0.0515 (12)	0.0491 (13)	0.0443 (12)	−0.0018 (10)	0.0104 (10)	−0.0040 (9)
C1	0.0490 (14)	0.0486 (15)	0.0505 (14)	−0.0026 (12)	0.0130 (11)	−0.0065 (12)
C2	0.0579 (15)	0.0553 (17)	0.0534 (15)	0.0034 (13)	0.0154 (13)	0.0005 (13)
C3	0.0564 (16)	0.0600 (18)	0.0634 (17)	0.0060 (13)	0.0134 (14)	−0.0076 (14)
C4	0.0529 (15)	0.067 (2)	0.0655 (18)	0.0034 (14)	0.0188 (14)	−0.0138 (15)
C5	0.0523 (15)	0.0639 (19)	0.0538 (15)	−0.0056 (13)	0.0195 (12)	−0.0095 (13)
C6	0.0464 (13)	0.0524 (16)	0.0508 (14)	−0.0025 (12)	0.0140 (11)	−0.0058 (12)
C7	0.0495 (14)	0.0462 (15)	0.0470 (14)	−0.0030 (11)	0.0130 (11)	−0.0019 (11)
C8	0.0474 (14)	0.0469 (15)	0.0446 (13)	−0.0029 (11)	0.0119 (11)	−0.0032 (11)
C9	0.0551 (15)	0.0542 (17)	0.0440 (14)	−0.0031 (12)	0.0136 (12)	0.0031 (11)
C10	0.0587 (16)	0.0499 (16)	0.0518 (15)	0.0000 (12)	0.0159 (13)	0.0066 (12)
C11	0.0517 (15)	0.0486 (16)	0.0548 (15)	0.0031 (12)	0.0106 (12)	0.0008 (12)
C12	0.0474 (14)	0.0437 (15)	0.0480 (14)	−0.0022 (11)	0.0108 (11)	−0.0047 (11)
C13	0.0478 (14)	0.0440 (15)	0.0515 (14)	−0.0022 (11)	0.0140 (11)	−0.0038 (11)
C14	0.0536 (15)	0.0539 (17)	0.0570 (16)	−0.0096 (12)	0.0211 (13)	−0.0116 (13)
C15	0.0624 (17)	0.068 (2)	0.0706 (19)	−0.0118 (15)	0.0260 (15)	−0.0182 (16)
C16	0.0716 (19)	0.076 (2)	0.070 (2)	−0.0209 (17)	0.0358 (16)	−0.0247 (17)
C17	0.081 (2)	0.082 (2)	0.0552 (17)	−0.0275 (18)	0.0271 (16)	−0.0105 (16)
C18	0.0663 (17)	0.0607 (19)	0.0588 (16)	−0.0094 (14)	0.0202 (14)	−0.0025 (14)
C19	0.0548 (15)	0.0552 (17)	0.0486 (15)	−0.0087 (12)	0.0145 (12)	−0.0072 (12)
C20	0.073 (2)	0.091 (3)	0.070 (2)	−0.0099 (18)	0.0166 (17)	0.0182 (18)
C21	0.087 (2)	0.073 (3)	0.131 (3)	0.0229 (19)	0.037 (2)	0.005 (2)
O3	0.106 (4)	0.102 (4)	0.070 (3)	−0.012 (3)	0.021 (3)	0.001 (2)
C22	0.024 (4)	0.086 (5)	0.050 (3)	0.011 (3)	0.016 (4)	0.010 (3)
O3'	0.130 (8)	0.127 (7)	0.088 (5)	−0.044 (6)	0.020 (5)	0.001 (5)
C22'	0.021 (7)	0.147 (13)	0.070 (7)	0.039 (7)	0.019 (6)	0.000 (6)

O1—C20	1.427 (3)	C10—H10	0.9500
O1—H1	0.8400	C11—C12	1.399 (4)
O2—C21	1.415 (4)	C11—H11	0.9500
O2—H2	0.8400	C12—C13	1.460 (4)
N1—C7	1.363 (3)	C14—C15	1.398 (4)
N1—C1	1.383 (3)	C14—C19	1.402 (4)
N1—H1N	0.866 (10)	C15—C16	1.372 (5)
N2—C7	1.324 (3)	C15—H15	0.9500
N2—C6	1.399 (3)	C16—C17	1.404 (5)
N3—C13	1.354 (3)	C16—H16	0.9500
N3—C19	1.381 (4)	C17—C18	1.372 (4)
N3—H3N	0.863 (10)	C17—H17	0.9500
N4—C13	1.321 (3)	C18—C19	1.385 (4)
N4—C14	1.386 (4)	C18—H18	0.9500
N5—C8	1.338 (3)	C20—H20A	0.9800
N5—C12	1.341 (3)	C20—H20B	0.9800
C1—C2	1.386 (4)	C20—H20C	0.9800
C1—C6	1.402 (4)	C21—H21A	0.9800
C2—C3	1.381 (4)	C21—H21B	0.9800
C2—H2A	0.9500	C21—H21C	0.9800
C3—C4	1.398 (4)	O3—C22	1.414 (10)
C3—H3	0.9500	O3—H3A	0.8400
C4—C5	1.367 (4)	C22—H22A	0.9800
C4—H4	0.9500	C22—H22B	0.9800
C5—C6	1.397 (4)	C22—H22C	0.9800
C5—H5	0.9500	O3'—C22'	1.324 (19)
C7—C8	1.459 (4)	O3'—H3'	0.8400
C8—C9	1.389 (3)	C22'—H22D	0.9800
C9—C10	1.383 (4)	C22'—H22E	0.9800
C9—H9	0.9500	C22'—H22F	0.9800
C10—C11	1.374 (4)
C20—O1—H1	109.5	N5—C12—C11	122.3 (3)
C21—O2—H2	109.5	N5—C12—C13	114.4 (2)
C7—N1—C1	107.3 (2)	C11—C12—C13	123.4 (2)
C7—N1—H1N	126 (2)	N4—C13—N3	112.8 (2)
C1—N1—H1N	126 (2)	N4—C13—C12	126.1 (2)
C7—N2—C6	104.5 (2)	N3—C13—C12	121.0 (2)
C13—N3—C19	107.4 (2)	N4—C14—C15	130.3 (3)
C13—N3—H3N	128 (3)	N4—C14—C19	109.9 (2)
C19—N3—H3N	125 (3)	C15—C14—C19	119.8 (3)
C13—N4—C14	105.0 (2)	C16—C15—C14	117.8 (3)
C8—N5—C12	117.9 (2)	C16—C15—H15	121.1
N1—C1—C2	132.8 (3)	C14—C15—H15	121.1
N1—C1—C6	105.1 (2)	C15—C16—C17	121.4 (3)
C2—C1—C6	122.1 (3)	C15—C16—H16	119.3
C3—C2—C1	116.7 (3)	C17—C16—H16	119.3
C3—C2—H2A	121.6	C18—C17—C16	121.7 (3)
C1—C2—H2A	121.6	C18—C17—H17	119.1
C2—C3—C4	121.4 (3)	C16—C17—H17	119.1
C2—C3—H3	119.3	C17—C18—C19	116.9 (3)
C4—C3—H3	119.3	C17—C18—H18	121.6
C5—C4—C3	122.2 (3)	C19—C18—H18	121.6
C5—C4—H4	118.9	N3—C19—C18	132.6 (3)
C3—C4—H4	118.9	N3—C19—C14	104.9 (2)
C4—C5—C6	117.3 (3)	C18—C19—C14	122.4 (3)
C4—C5—H5	121.4	O1—C20—H20A	109.5
C6—C5—H5	121.4	O1—C20—H20B	109.5
C5—C6—N2	129.6 (3)	H20A—C20—H20B	109.5
C5—C6—C1	120.4 (3)	O1—C20—H20C	109.5
N2—C6—C1	110.1 (2)	H20A—C20—H20C	109.5
N2—C7—N1	113.1 (2)	H20B—C20—H20C	109.5
N2—C7—C8	126.1 (2)	O2—C21—H21A	109.5
N1—C7—C8	120.8 (2)	O2—C21—H21B	109.5
N5—C8—C9	123.3 (2)	H21A—C21—H21B	109.5
N5—C8—C7	114.4 (2)	O2—C21—H21C	109.5
C9—C8—C7	122.2 (2)	H21A—C21—H21C	109.5
C10—C9—C8	118.2 (3)	H21B—C21—H21C	109.5
C10—C9—H9	120.9	C22'—O3'—H3'	109.5
C8—C9—H9	120.9	O3'—C22'—H22D	109.5
C11—C10—C9	119.5 (2)	O3'—C22'—H22E	109.5
C11—C10—H10	120.3	H22D—C22'—H22E	109.5
C9—C10—H10	120.3	O3'—C22'—H22F	109.5
C10—C11—C12	118.8 (2)	H22D—C22'—H22F	109.5
C10—C11—H11	120.6	H22E—C22'—H22F	109.5
C12—C11—H11	120.6
C7—N1—C1—C2	179.1 (3)	C9—C10—C11—C12	0.2 (4)
C7—N1—C1—C6	−0.4 (3)	C8—N5—C12—C11	−0.5 (3)
N1—C1—C2—C3	179.4 (3)	C8—N5—C12—C13	−179.5 (2)
C6—C1—C2—C3	−1.1 (4)	C10—C11—C12—N5	0.4 (4)
C1—C2—C3—C4	0.1 (4)	C10—C11—C12—C13	179.4 (2)
C2—C3—C4—C5	0.4 (4)	C14—N4—C13—N3	1.0 (3)
C3—C4—C5—C6	0.0 (4)	C14—N4—C13—C12	−178.6 (2)
C4—C5—C6—N2	179.5 (2)	C19—N3—C13—N4	−0.9 (3)
C4—C5—C6—C1	−1.0 (4)	C19—N3—C13—C12	178.7 (2)
C7—N2—C6—C5	178.7 (3)	N5—C12—C13—N4	179.9 (2)
C7—N2—C6—C1	−0.9 (3)	C11—C12—C13—N4	0.8 (4)
N1—C1—C6—C5	−178.8 (2)	N5—C12—C13—N3	0.3 (3)
C2—C1—C6—C5	1.6 (4)	C11—C12—C13—N3	−178.7 (2)
N1—C1—C6—N2	0.8 (3)	C13—N4—C14—C15	178.1 (3)
C2—C1—C6—N2	−178.8 (2)	C13—N4—C14—C19	−0.7 (3)
C6—N2—C7—N1	0.6 (3)	N4—C14—C15—C16	−178.7 (3)
C6—N2—C7—C8	179.5 (2)	C19—C14—C15—C16	0.1 (4)
C1—N1—C7—N2	−0.1 (3)	C14—C15—C16—C17	−0.2 (4)
C1—N1—C7—C8	−179.1 (2)	C15—C16—C17—C18	0.6 (5)
C12—N5—C8—C9	−0.1 (3)	C16—C17—C18—C19	−0.9 (4)
C12—N5—C8—C7	−179.9 (2)	C13—N3—C19—C18	−177.7 (3)
N2—C7—C8—N5	−178.7 (2)	C13—N3—C19—C14	0.4 (3)
N1—C7—C8—N5	0.1 (3)	C17—C18—C19—N3	178.6 (3)
N2—C7—C8—C9	1.5 (4)	C17—C18—C19—C14	0.8 (4)
N1—C7—C8—C9	−179.7 (2)	N4—C14—C19—N3	0.2 (3)
N5—C8—C9—C10	0.7 (4)	C15—C14—C19—N3	−178.7 (2)
C7—C8—C9—C10	−179.6 (2)	N4—C14—C19—C18	178.6 (2)
C8—C9—C10—C11	−0.7 (4)	C15—C14—C19—C18	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.83	2.670 (3)	176
O2—H2···N4	0.84	1.91	2.741 (3)	168
N1—H1N···O1	0.87 (1)	2.07 (1)	2.927 (3)	171 (3)
N3—H3N···O1	0.86 (1)	2.07 (1)	2.925 (3)	171 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.83	2.670 (3)	176
O2—H2⋯N4	0.84	1.91	2.741 (3)	168
N1—H1N⋯O1	0.866 (10)	2.069 (12)	2.927 (3)	171 (3)
N3—H3N⋯O1	0.863 (10)	2.069 (12)	2.925 (3)	171 (4)

Symmetry code: (i) .