1,6-Bis(1-benzimidazolyl)­hexane trihydrate

In the title compound, C₂₀H₂₂N₄·3H₂O, the asymmetric unit contains one half of the organic mol­ecule, the other half being related by twofold rotational symmetry. The O atom of one of the solvent water mol­ecules lies on a twofold axis. In the crystal, the molecular organization is stabilized by well-defined weak intermolecular interactions that lead to the formation of a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.155
• Data-to-parameter ratio = 15.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.105


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 1995); cell refinement: SMART; data reduction: SHELXTL (Bruker 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,6-bis(1-benzimidazolyl)hexane trihydrate

Crystal data

C20H22N4·3H2O	Dx = 1.244 Mg m^−3
Mr = 372.46	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 1646 reflections
a = 14.4368 (19) Å	θ = 2.4–27.5°
b = 16.426 (2) Å	µ = 0.09 mm^−1
c = 8.3834 (12) Å	T = 294 K
V = 1988.0 (5) Å^3	Block, colourless
Z = 4	0.20 × 0.18 × 0.16 mm
F(000) = 800

Data collection

Bruker CCD area-detector diffractometer	2120 independent reflections
Radiation source: fine-focus sealed tube	721 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.105
φ and ω scans	θmax = 26.8°, θmin = 2.5°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −18→15
Tmin = 0.983, Tmax = 0.987	k = −20→20
11751 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ^2(Fo^2) + (0.0685P)^2] where P = (Fo^2 + 2Fc^2)/3
2120 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.19 e Å^−3
3 restraints	Δρmin = −0.20 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.60971 (17)	0.07536 (14)	0.4371 (3)	0.0481 (7)
N2	0.66711 (18)	0.00600 (15)	0.6445 (3)	0.0563 (8)
C1	0.5552 (2)	0.09565 (16)	0.5667 (4)	0.0426 (7)
C2	0.4790 (2)	0.1454 (2)	0.5804 (4)	0.0596 (9)
H2	0.4544	0.1731	0.4934	0.072*
C3	0.4412 (2)	0.1517 (2)	0.7310 (5)	0.0669 (10)
H3	0.3894	0.1844	0.7461	0.080*
C4	0.4782 (3)	0.1107 (2)	0.8605 (4)	0.0688 (10)
H4	0.4517	0.1175	0.9607	0.083*
C5	0.5533 (2)	0.06041 (19)	0.8437 (4)	0.0589 (9)
H5	0.5774	0.0323	0.9306	0.071*
C6	0.5922 (2)	0.05269 (17)	0.6942 (4)	0.0462 (8)
C7	0.6731 (2)	0.02234 (19)	0.4911 (4)	0.0557 (9)
H7	0.7177	−0.0010	0.4254	0.067*
C8	0.6003 (2)	0.10721 (19)	0.2749 (3)	0.0579 (9)
H8A	0.5358	0.1038	0.2429	0.069*
H8B	0.6361	0.0734	0.2027	0.069*
C9	0.6323 (2)	0.19400 (18)	0.2594 (4)	0.0532 (9)
H9A	0.6023	0.2261	0.3416	0.064*
H9B	0.6119	0.2148	0.1570	0.064*
C10	0.7354 (2)	0.20608 (16)	0.2726 (3)	0.0493 (8)
H10A	0.7569	0.1807	0.3703	0.059*
H10B	0.7653	0.1786	0.1841	0.059*
O1W	0.17220 (19)	0.34376 (14)	0.2394 (3)	0.0789 (8)
O2W	0.2500	0.2500	0.4876 (4)	0.0740 (10)
H1O1	0.186 (3)	0.398 (2)	0.250 (6)	0.177 (14)*
H2O1	0.203 (3)	0.312 (3)	0.311 (6)	0.177 (14)*
H1O2	0.283 (3)	0.285 (3)	0.550 (5)	0.177 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0598 (17)	0.0459 (15)	0.0387 (16)	−0.0055 (13)	−0.0008 (14)	0.0015 (13)
N2	0.0693 (19)	0.0455 (16)	0.0540 (19)	0.0002 (14)	−0.0004 (15)	0.0022 (14)
C1	0.0488 (19)	0.0430 (17)	0.0361 (18)	−0.0070 (15)	−0.0004 (16)	−0.0025 (16)
C2	0.050 (2)	0.067 (2)	0.061 (2)	−0.0029 (18)	−0.0050 (19)	−0.001 (2)
C3	0.054 (2)	0.067 (2)	0.080 (3)	0.0044 (18)	0.013 (2)	−0.001 (2)
C4	0.076 (3)	0.071 (3)	0.059 (3)	−0.008 (2)	0.022 (2)	0.002 (2)
C5	0.073 (2)	0.058 (2)	0.045 (2)	−0.013 (2)	−0.0022 (19)	0.0072 (18)
C6	0.054 (2)	0.0399 (17)	0.045 (2)	−0.0047 (16)	0.0024 (17)	0.0006 (15)
C7	0.061 (2)	0.048 (2)	0.059 (3)	−0.0009 (17)	0.0100 (18)	−0.0031 (18)
C8	0.069 (2)	0.065 (2)	0.039 (2)	−0.0150 (18)	−0.0051 (17)	0.0061 (16)
C9	0.059 (2)	0.057 (2)	0.0432 (19)	−0.0057 (17)	−0.0048 (16)	0.0084 (16)
C10	0.055 (2)	0.0486 (17)	0.0444 (19)	0.0006 (16)	−0.0031 (16)	0.0014 (14)
O1W	0.102 (2)	0.0681 (17)	0.0663 (18)	0.0143 (15)	0.0000 (14)	−0.0056 (15)
O2W	0.103 (3)	0.068 (2)	0.051 (2)	−0.009 (2)	0.000	0.000

Geometric parameters (Å, º)

N1—C7	1.342 (4)	C5—H5	0.93
N1—C1	1.382 (3)	C7—H7	0.93
N1—C8	1.464 (3)	C8—C9	1.504 (4)
N2—C7	1.316 (4)	C8—H8A	0.97
N2—C6	1.390 (3)	C8—H8B	0.97
C1—C2	1.376 (4)	C9—C10	1.506 (4)
C1—C6	1.388 (4)	C9—H9A	0.97
C2—C3	1.379 (4)	C9—H9B	0.97
C2—H2	0.93	C10—C10^i	1.503 (5)
C3—C4	1.384 (4)	C10—H10A	0.97
C3—H3	0.93	C10—H10B	0.97
C4—C5	1.370 (4)	O1W—H1O1	0.92 (3)
C4—H4	0.93	O1W—H2O1	0.91 (3)
C5—C6	1.378 (4)	O2W—H1O2	0.91 (3)
C7—N1—C1	106.2 (2)	N2—C7—N1	114.6 (3)
C7—N1—C8	127.5 (3)	N2—C7—H7	122.7
C1—N1—C8	126.3 (3)	N1—C7—H7	122.7
C7—N2—C6	103.4 (3)	N1—C8—C9	113.0 (2)
C2—C1—N1	131.6 (3)	N1—C8—H8A	109.0
C2—C1—C6	123.0 (3)	C9—C8—H8A	109.0
N1—C1—C6	105.3 (3)	N1—C8—H8B	109.0
C1—C2—C3	115.9 (3)	C9—C8—H8B	109.0
C1—C2—H2	122.1	H8A—C8—H8B	107.8
C3—C2—H2	122.1	C8—C9—C10	115.0 (3)
C2—C3—C4	122.0 (3)	C8—C9—H9A	108.5
C2—C3—H3	119.0	C10—C9—H9A	108.5
C4—C3—H3	119.0	C8—C9—H9B	108.5
C5—C4—C3	121.2 (3)	C10—C9—H9B	108.5
C5—C4—H4	119.4	H9A—C9—H9B	107.5
C3—C4—H4	119.4	C10^i—C10—C9	113.8 (3)
C4—C5—C6	118.1 (3)	C10^i—C10—H10A	108.8
C4—C5—H5	121.0	C9—C10—H10A	108.8
C6—C5—H5	121.0	C10^i—C10—H10B	108.8
C5—C6—C1	119.8 (3)	C9—C10—H10B	108.8
C5—C6—N2	129.8 (3)	H10A—C10—H10B	107.7
C1—C6—N2	110.4 (3)	H1O1—O1W—H2O1	112 (5)
C7—N1—C1—C2	−178.1 (3)	N1—C1—C6—C5	179.4 (3)
C8—N1—C1—C2	3.0 (5)	C2—C1—C6—N2	178.4 (3)
C7—N1—C1—C6	0.9 (3)	N1—C1—C6—N2	−0.7 (3)
C8—N1—C1—C6	−178.0 (2)	C7—N2—C6—C5	−179.9 (3)
N1—C1—C2—C3	180.0 (3)	C7—N2—C6—C1	0.3 (3)
C6—C1—C2—C3	1.1 (4)	C6—N2—C7—N1	0.4 (3)
C1—C2—C3—C4	0.4 (5)	C1—N1—C7—N2	−0.8 (3)
C2—C3—C4—C5	−1.5 (5)	C8—N1—C7—N2	178.0 (2)
C3—C4—C5—C6	1.1 (5)	C7—N1—C8—C9	−105.7 (3)
C4—C5—C6—C1	0.3 (4)	C1—N1—C8—C9	73.0 (4)
C4—C5—C6—N2	−179.5 (3)	N1—C8—C9—C10	70.6 (3)
C2—C1—C6—C5	−1.5 (4)	C8—C9—C10—C10^i	−174.43 (18)

Symmetry code: (i) −x+3/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1O1···N2^ii	0.92 (3)	2.00 (4)	2.838 (3)	151 (4)
O2W—H1O2···O1W^iii	0.91 (5)	1.97 (4)	2.844 (4)	161 (4)
O1W—H2O1···O2W	0.91 (5)	1.92 (5)	2.822 (4)	170 (4)
C9—H9A···Cg(A)^iv	0.97	3.26	3.754 (3)	114
C10—H10B···Cg(B)^v	0.97	2.86	3.729 (3)	150

Symmetry codes: (ii) x−1/2, y+1/2, −z+1; (iii) −x+1/2, y, z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+3/2, y, z−1/2.