Adipic acid-2,6-bis-(1H-benzimidazol-2-yl)pyridine-water (1/2/4).

The asymmetric unit of the title hydrated co-crystal, 2C19H13N5·C6H10O4·4H2O, consists of one 2,6-bis-(1H-benzimidazol-2-yl)pyridine mol-ecule, half of an adipic acid mol-ecule (bis-ected by an inversion center) and two water solvates. In the crystal, N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds and π-π inter-actions [centroid-centroid distances = 3.769 (2) and 3.731 (2) Å] form a three-dimensional supra-molecular structure.

Related literature

For related structures, see: Boča et al. (2000 ▶); Chetia & Iyer (2006 ▶, 2007 ▶); Xiao et al. (2010 ▶); Freire et al. (2003 ▶); Lin et al. (2012 ▶).

Experimental

Crystal data

2C19H13N5·C6H10O4·4n class="Chemical">H2O

M = 840.90

Triclinic,

a = 9.0709 (18) Å

b = 9.6882 (19) Å

c = 12.311 (3) Å

α = 88.93 (3)°

β = 83.12 (3)°

γ = 75.14 (3)°

V = 1038.1 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.25 × 0.18 × 0.16 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

10214 measured reflections

4705 independent reflections

3555 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.163

S = 1.15

4705 reflections

368 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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: WinGX (Farrugia, 2012) ▶.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047861/bg2486sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047861/bg2486Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047861/bg2486Isup3.cml

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

2C19H13N5·C6H10O4·4H2O	Z = 1
Mr = 840.90	F(000) = 442
Triclinic, P1	Dx = 1.345 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0709 (18) Å	Cell parameters from 25 reflections
b = 9.6882 (19) Å	θ = 4–14°
c = 12.311 (3) Å	µ = 0.10 mm−1
α = 88.93 (3)°	T = 295 K
β = 83.12 (3)°	Block, yellow
γ = 75.14 (3)°	0.25 × 0.18 × 0.16 mm
V = 1038.1 (4) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 3.0°
Graphite monochromator	h = −11→11
ω scans	k = −12→12
10214 measured reflections	l = −15→15
4705 independent reflections	3 standard reflections every 100 reflections
3555 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.1P)2 + 0.0268P] where P = (Fo2 + 2Fc2)/3
4705 reflections	(Δ/σ)max < 0.001
368 parameters	Δρmax = 0.36 e Å−3
7 restraints	Δρmin = −0.19 e Å−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
N1	0.13159 (14)	0.33800 (13)	−0.15941 (10)	0.0488 (3)
N2	0.11534 (14)	0.56273 (13)	−0.10937 (10)	0.0469 (3)
H4	0.142 (2)	0.632 (2)	−0.0672 (17)	0.070 (5)*
N3	0.30720 (13)	0.47411 (12)	0.04908 (9)	0.0425 (3)
N4	0.35862 (15)	0.69020 (12)	0.16663 (10)	0.0461 (3)
H5	0.296 (2)	0.718 (2)	0.1169 (17)	0.071 (6)*
N5	0.51881 (14)	0.53946 (12)	0.26517 (10)	0.0467 (3)
C1	0.03749 (17)	0.43165 (17)	−0.22421 (12)	0.0502 (3)
C2	−0.0392 (2)	0.4018 (2)	−0.30889 (15)	0.0660 (5)
H2B	−0.029 (3)	0.302 (3)	−0.331 (2)	0.108 (9)*
C3	−0.1263 (2)	0.5167 (3)	−0.36062 (17)	0.0737 (5)
H3B	−0.177 (2)	0.500 (2)	−0.4221 (17)	0.075 (6)*
C4	−0.1367 (2)	0.6559 (3)	−0.32926 (17)	0.0738 (6)
H4B	−0.203 (2)	0.737 (2)	−0.3704 (18)	0.083 (6)*
C5	−0.0618 (2)	0.6887 (2)	−0.24504 (16)	0.0625 (4)
H5B	−0.071 (2)	0.784 (2)	−0.2255 (17)	0.072 (6)*
C6	0.02658 (16)	0.57252 (17)	−0.19362 (12)	0.0495 (4)
C7	0.17580 (15)	0.42054 (14)	−0.09313 (11)	0.0436 (3)
C8	0.28186 (15)	0.37145 (14)	−0.01174 (11)	0.0423 (3)
C9	0.35464 (18)	0.22746 (15)	−0.00130 (13)	0.0500 (4)
H9A	0.3296 (19)	0.1624 (19)	−0.0465 (15)	0.053 (4)*
C10	0.45920 (19)	0.18978 (15)	0.07321 (13)	0.0533 (4)
H10A	0.517 (2)	0.086 (2)	0.0801 (15)	0.064 (5)*
C11	0.48672 (19)	0.29346 (15)	0.13676 (13)	0.0496 (4)
H11A	0.553 (2)	0.2771 (19)	0.1892 (15)	0.058 (5)*
C12	0.40660 (15)	0.43502 (14)	0.12290 (11)	0.0423 (3)
C13	0.42912 (15)	0.55179 (14)	0.18674 (11)	0.0424 (3)
C14	0.50736 (17)	0.67897 (15)	0.29760 (12)	0.0461 (3)
C15	0.5824 (2)	0.72962 (19)	0.37449 (15)	0.0590 (4)
H15A	0.653 (3)	0.659 (2)	0.4172 (19)	0.085 (6)*
C16	0.5557 (2)	0.8759 (2)	0.38559 (16)	0.0678 (5)
H16A	0.607 (2)	0.915 (2)	0.4359 (18)	0.080 (6)*
C17	0.4553 (2)	0.96933 (19)	0.32354 (16)	0.0686 (5)
H17A	0.442 (2)	1.074 (2)	0.3320 (17)	0.080 (6)*
C18	0.3784 (2)	0.92146 (17)	0.24903 (14)	0.0588 (4)
H18A	0.308 (2)	0.984 (2)	0.2049 (17)	0.072 (6)*
C19	0.40766 (17)	0.77399 (15)	0.23620 (12)	0.0465 (3)
O1	0.67965 (16)	0.37143 (12)	0.40769 (11)	0.0688 (4)
H1	0.630 (2)	0.411 (2)	0.3538 (14)	0.084 (7)*
O2	0.74254 (17)	0.17221 (13)	0.30895 (11)	0.0732 (4)
C20	0.75243 (17)	0.23700 (16)	0.38907 (13)	0.0491 (3)
C21	0.8489 (2)	0.17588 (17)	0.47764 (14)	0.0538 (4)
H21A	0.784 (3)	0.179 (2)	0.5432 (19)	0.079 (6)*
H21B	0.915 (2)	0.250 (2)	0.4912 (16)	0.073 (6)*
C22	0.9496 (2)	0.02613 (17)	0.45481 (14)	0.0543 (4)
H22A	0.883 (2)	−0.040 (2)	0.4464 (16)	0.069 (5)*
H22B	1.019 (2)	0.022 (2)	0.3830 (17)	0.071 (5)*
O1W	0.14244 (18)	0.04491 (14)	0.85092 (11)	0.0742 (4)
O2W	0.14234 (16)	0.82851 (14)	0.01294 (13)	0.0751 (4)
H1WA	0.153 (3)	0.1282 (13)	0.8350 (18)	0.102 (8)*
H1WB	0.172 (3)	−0.0080 (19)	0.7943 (13)	0.093 (8)*
H2WB	0.064 (3)	0.870 (3)	0.058 (2)	0.152 (13)*
H2WA	0.151 (3)	0.896 (2)	−0.0326 (18)	0.126 (10)*

	U11	U22	U33	U12	U13	U23
N1	0.0533 (7)	0.0439 (7)	0.0461 (7)	−0.0062 (5)	−0.0072 (5)	−0.0025 (5)
N2	0.0474 (6)	0.0400 (6)	0.0505 (7)	−0.0060 (5)	−0.0065 (5)	0.0026 (5)
N3	0.0460 (6)	0.0359 (5)	0.0420 (6)	−0.0054 (5)	−0.0027 (5)	0.0022 (4)
N4	0.0533 (7)	0.0361 (6)	0.0453 (7)	−0.0042 (5)	−0.0081 (5)	0.0051 (5)
N5	0.0524 (7)	0.0387 (6)	0.0450 (6)	−0.0034 (5)	−0.0080 (5)	−0.0001 (5)
C1	0.0489 (8)	0.0545 (8)	0.0434 (8)	−0.0071 (7)	−0.0036 (6)	−0.0008 (6)
C2	0.0642 (10)	0.0800 (13)	0.0525 (10)	−0.0130 (9)	−0.0134 (8)	−0.0017 (9)
C3	0.0645 (11)	0.0970 (15)	0.0574 (11)	−0.0116 (10)	−0.0188 (9)	0.0053 (10)
C4	0.0572 (10)	0.0880 (14)	0.0688 (12)	−0.0038 (10)	−0.0142 (9)	0.0243 (11)
C5	0.0539 (9)	0.0595 (10)	0.0681 (11)	−0.0048 (8)	−0.0074 (8)	0.0158 (8)
C6	0.0429 (7)	0.0524 (8)	0.0491 (8)	−0.0068 (6)	−0.0025 (6)	0.0079 (6)
C7	0.0452 (7)	0.0374 (7)	0.0438 (7)	−0.0047 (6)	−0.0005 (6)	0.0003 (5)
C8	0.0449 (7)	0.0379 (7)	0.0403 (7)	−0.0060 (6)	−0.0005 (5)	0.0001 (5)
C9	0.0589 (8)	0.0353 (7)	0.0522 (8)	−0.0058 (6)	−0.0058 (7)	−0.0029 (6)
C10	0.0638 (9)	0.0345 (7)	0.0552 (9)	−0.0002 (7)	−0.0097 (7)	0.0018 (6)
C11	0.0568 (8)	0.0379 (7)	0.0498 (8)	−0.0027 (6)	−0.0110 (7)	0.0047 (6)
C12	0.0461 (7)	0.0363 (6)	0.0410 (7)	−0.0056 (6)	−0.0025 (5)	0.0021 (5)
C13	0.0451 (7)	0.0354 (6)	0.0424 (7)	−0.0034 (5)	−0.0038 (5)	0.0042 (5)
C14	0.0520 (8)	0.0401 (7)	0.0423 (7)	−0.0064 (6)	−0.0018 (6)	−0.0031 (6)
C15	0.0625 (9)	0.0558 (9)	0.0554 (9)	−0.0064 (8)	−0.0111 (7)	−0.0087 (7)
C16	0.0759 (11)	0.0624 (10)	0.0662 (11)	−0.0187 (9)	−0.0073 (9)	−0.0187 (9)
C17	0.0898 (13)	0.0429 (8)	0.0714 (12)	−0.0168 (9)	−0.0015 (10)	−0.0101 (8)
C18	0.0761 (11)	0.0375 (7)	0.0587 (10)	−0.0090 (7)	−0.0035 (8)	0.0002 (7)
C19	0.0543 (8)	0.0387 (7)	0.0430 (7)	−0.0078 (6)	−0.0006 (6)	0.0009 (6)
O1	0.0873 (9)	0.0462 (6)	0.0612 (7)	0.0133 (6)	−0.0288 (7)	−0.0021 (5)
O2	0.0936 (9)	0.0482 (6)	0.0773 (8)	0.0008 (6)	−0.0494 (7)	−0.0055 (6)
C20	0.0528 (8)	0.0410 (7)	0.0520 (8)	−0.0055 (6)	−0.0152 (6)	0.0062 (6)
C21	0.0598 (9)	0.0492 (8)	0.0475 (9)	−0.0009 (7)	−0.0154 (7)	0.0048 (6)
C22	0.0600 (9)	0.0463 (8)	0.0543 (9)	−0.0033 (7)	−0.0209 (8)	0.0062 (7)
O1W	0.1059 (10)	0.0511 (7)	0.0632 (8)	−0.0195 (7)	−0.0014 (7)	−0.0007 (6)
O2W	0.0710 (8)	0.0589 (7)	0.0809 (10)	0.0058 (6)	−0.0037 (7)	0.0200 (7)

N1—C7	1.3166 (19)	C11—C12	1.3957 (19)
N1—C1	1.388 (2)	C11—H11A	0.917 (19)
N2—C7	1.3664 (17)	C12—C13	1.459 (2)
N2—C6	1.375 (2)	C14—C15	1.394 (2)
N2—H4	0.95 (2)	C14—C19	1.395 (2)
N3—C8	1.3375 (18)	C15—C16	1.381 (3)
N3—C12	1.3381 (19)	C15—H15A	1.00 (2)
N4—C13	1.3617 (17)	C16—C17	1.397 (3)
N4—C19	1.376 (2)	C16—H16A	0.96 (2)
N4—H5	0.88 (2)	C17—C18	1.370 (3)
N5—C13	1.3201 (18)	C17—H17A	1.00 (2)
N5—C14	1.3911 (18)	C18—C19	1.393 (2)
C1—C2	1.394 (2)	C18—H18A	0.98 (2)
C1—C6	1.398 (2)	O1—C20	1.3109 (19)
C2—C3	1.383 (3)	O1—H1	0.873 (10)
C2—H2B	0.99 (3)	O2—C20	1.203 (2)
C3—C4	1.386 (3)	C20—C21	1.498 (2)
C3—H3B	0.97 (2)	C21—C22	1.514 (2)
C4—C5	1.388 (3)	C21—H21A	0.94 (2)
C4—H4B	1.03 (2)	C21—H21B	1.07 (2)
C5—C6	1.394 (2)	C22—C22i	1.522 (3)
C5—H5B	0.94 (2)	C22—H22A	1.001 (19)
C7—C8	1.461 (2)	C22—H22B	1.02 (2)
C8—C9	1.3927 (19)	O1W—H1WA	0.854 (10)
C9—C10	1.376 (2)	O1W—H1WB	0.848 (9)
C9—H9A	0.935 (18)	O2W—H2WB	0.860 (10)
C10—C11	1.374 (2)	O2W—H2WA	0.865 (10)
C10—H10A	1.012 (18)
C7—N1—C1	104.88 (12)	N3—C12—C11	122.93 (14)
C7—N2—C6	106.77 (13)	N3—C12—C13	115.23 (12)
C7—N2—H4	120.0 (12)	C11—C12—C13	121.82 (14)
C6—N2—H4	133.2 (12)	N5—C13—N4	112.69 (13)
C8—N3—C12	117.85 (12)	N5—C13—C12	126.24 (12)
C13—N4—C19	107.10 (13)	N4—C13—C12	121.05 (13)
C13—N4—H5	125.1 (13)	N5—C14—C15	129.82 (15)
C19—N4—H5	127.8 (13)	N5—C14—C19	109.63 (13)
C13—N5—C14	105.00 (12)	C15—C14—C19	120.50 (15)
N1—C1—C2	129.23 (17)	C16—C15—C14	117.41 (17)
N1—C1—C6	109.80 (14)	C16—C15—H15A	124.0 (13)
C2—C1—C6	120.96 (16)	C14—C15—H15A	118.6 (13)
C3—C2—C1	117.3 (2)	C15—C16—C17	121.28 (17)
C3—C2—H2B	122.5 (16)	C15—C16—H16A	120.3 (13)
C1—C2—H2B	120.2 (16)	C17—C16—H16A	118.4 (13)
C2—C3—C4	121.2 (2)	C18—C17—C16	122.09 (16)
C2—C3—H3B	119.3 (13)	C18—C17—H17A	119.2 (12)
C4—C3—H3B	119.5 (13)	C16—C17—H17A	118.7 (12)
C3—C4—C5	122.70 (18)	C17—C18—C19	116.66 (17)
C3—C4—H4B	117.8 (13)	C17—C18—H18A	123.8 (12)
C5—C4—H4B	119.5 (13)	C19—C18—H18A	119.6 (12)
C4—C5—C6	115.93 (19)	N4—C19—C18	132.36 (15)
C4—C5—H5B	121.0 (13)	N4—C19—C14	105.57 (12)
C6—C5—H5B	123.1 (13)	C18—C19—C14	122.03 (15)
N2—C6—C5	132.52 (16)	C20—O1—H1	113.3 (16)
N2—C6—C1	105.55 (13)	O2—C20—O1	123.00 (14)
C5—C6—C1	121.93 (17)	O2—C20—C21	124.71 (14)
N1—C7—N2	112.99 (13)	O1—C20—C21	112.28 (14)
N1—C7—C8	125.67 (12)	C20—C21—C22	114.80 (14)
N2—C7—C8	121.32 (13)	C20—C21—H21A	108.3 (13)
N3—C8—C9	122.74 (14)	C22—C21—H21A	110.4 (13)
N3—C8—C7	115.52 (12)	C20—C21—H21B	106.6 (10)
C9—C8—C7	121.71 (13)	C22—C21—H21B	111.9 (11)
C10—C9—C8	118.51 (14)	H21A—C21—H21B	104.2 (17)
C10—C9—H9A	124.2 (11)	C21—C22—C22i	111.97 (18)
C8—C9—H9A	117.3 (11)	C21—C22—H22A	109.3 (11)
C11—C10—C9	119.71 (13)	C22i—C22—H22A	109.8 (11)
C11—C10—H10A	120.1 (10)	C21—C22—H22B	110.5 (11)
C9—C10—H10A	120.2 (10)	C22i—C22—H22B	108.1 (11)
C10—C11—C12	118.22 (14)	H22A—C22—H22B	107.0 (15)
C10—C11—H11A	125.1 (11)	H1WA—O1W—H1WB	108.7 (18)
C12—C11—H11A	116.6 (11)	H2WB—O2W—H2WA	102.4 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H4···O2W	0.95 (2)	2.16 (2)	3.084 (2)	163.3 (18)
N4—H5···O2W	0.88 (2)	2.08 (2)	2.945 (2)	167.6 (18)
O1—H1···N5	0.87 (1)	1.83 (1)	2.6731 (19)	163 (2)
O1W—H1WA···N1ii	0.85 (1)	1.99 (1)	2.8169 (18)	162 (2)
O1W—H1WB···O2iii	0.85 (1)	1.99 (1)	2.815 (2)	165 (2)
O2W—H2WB···O1Wiv	0.86 (1)	2.05 (1)	2.898 (2)	170 (3)
O2W—H2WA···O1Wv	0.87 (1)	2.01 (1)	2.867 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H4⋯O2W	0.95 (2)	2.16 (2)	3.084 (2)	163.3 (18)
N4—H5⋯O2W	0.88 (2)	2.08 (2)	2.945 (2)	167.6 (18)
O1—H1⋯N5	0.87 (1)	1.83 (1)	2.6731 (19)	163 (2)
O1W—H1WA⋯N1i	0.85 (1)	1.99 (1)	2.8169 (18)	162 (2)
O1W—H1WB⋯O2ii	0.85 (1)	1.99 (1)	2.815 (2)	165 (2)
O2W—H2WB⋯O1W iii	0.86 (1)	2.05 (1)	2.898 (2)	170 (3)
O2W—H2WA⋯O1W iv	0.87 (1)	2.01 (1)	2.867 (2)	171 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .