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In the approximately mirror-symmetric mol­ecule of the title compound, C18H18N4O·H2O, each benzimidazole group is essentially planar and the dihedral angle between them is 75.10 (5)°. O—H...N and C—H...O hydrogen bonds generate a centrosymmetric R44(10) cluster of two organic and two water mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019088/cf2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019088/cf2024Isup2.hkl
Contains datablock I

CCDC reference: 610728

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.101
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C12 .. 6.19 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Bis[2-(1H-benzimidazol-1-yl)ethyl] ether monohydrate top
Crystal data top
C18H18N4O·H2ODx = 1.284 Mg m3
Mr = 324.38Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 4253 reflections
a = 18.230 (3) Åθ = 2.4–25.8°
b = 9.4065 (16) ŵ = 0.09 mm1
c = 19.578 (3) ÅT = 293 K
V = 3357.2 (10) Å3Plate, colourless
Z = 80.46 × 0.34 × 0.10 mm
F(000) = 1376
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3319 independent reflections
Radiation source: fine-focus sealed tube2536 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 2.1°
ω scansh = 1522
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1111
Tmin = 0.961, Tmax = 0.991l = 2420
17849 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0436P)2 + 0.4543P]
where P = (Fo2 + 2Fc2)/3
3319 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.15 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.16613 (5)0.57575 (11)0.34219 (5)0.0554 (3)
N10.07058 (6)0.34889 (12)0.30281 (6)0.0503 (3)
N20.03898 (6)0.23259 (13)0.39807 (6)0.0554 (3)
N30.20997 (7)0.60202 (13)0.48353 (6)0.0562 (3)
N40.15284 (7)0.44652 (17)0.55207 (7)0.0675 (4)
C10.08199 (7)0.20679 (14)0.28914 (7)0.0465 (3)
C20.10645 (8)0.13668 (18)0.23108 (8)0.0628 (4)
H2B0.11900.18570.19150.075*
C30.11119 (10)0.0083 (2)0.23500 (10)0.0751 (5)
H3A0.12770.05910.19720.090*
C40.09198 (9)0.08159 (18)0.29407 (10)0.0732 (5)
H4B0.09630.18010.29480.088*
C50.06682 (8)0.01280 (16)0.35151 (9)0.0600 (4)
H5A0.05370.06300.39060.072*
C60.06177 (7)0.13511 (15)0.34888 (7)0.0471 (3)
C70.04553 (8)0.35586 (16)0.36789 (8)0.0552 (4)
H7A0.03400.44120.38930.066*
C80.09085 (9)0.46878 (16)0.25954 (8)0.0607 (4)
H8A0.05590.54530.26620.073*
H8B0.08850.43990.21200.073*
C90.16667 (9)0.52209 (17)0.27510 (7)0.0546 (4)
H9A0.20190.44530.27120.065*
H9B0.18030.59640.24320.065*
C100.23183 (8)0.64483 (16)0.36116 (7)0.0574 (4)
H10A0.24370.71860.32840.069*
H10B0.27200.57720.36240.069*
C110.22045 (10)0.70860 (17)0.43062 (9)0.0686 (5)
H11A0.26270.76660.44220.082*
H11B0.17780.77030.42930.082*
C120.14570 (8)0.5456 (2)0.50569 (8)0.0670 (5)
H12A0.10030.57500.48920.080*
C130.26440 (8)0.53302 (15)0.51928 (7)0.0485 (3)
C140.34028 (8)0.54576 (17)0.51741 (8)0.0575 (4)
H14A0.36350.61200.48960.069*
C150.37896 (9)0.45572 (19)0.55871 (8)0.0655 (4)
H15A0.42990.46070.55880.079*
C160.34446 (10)0.35711 (19)0.60047 (8)0.0666 (4)
H16A0.37290.29720.62740.080*
C170.26937 (9)0.34559 (17)0.60311 (7)0.0622 (4)
H17A0.24670.27980.63160.075*
C180.22842 (8)0.43598 (16)0.56154 (7)0.0525 (4)
O1W0.00965 (7)0.29809 (17)0.54666 (8)0.0775 (4)
H1W10.0541 (14)0.333 (2)0.5576 (10)0.105 (8)*
H2W10.0155 (14)0.262 (3)0.5045 (15)0.131 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0492 (6)0.0694 (7)0.0476 (5)0.0113 (5)0.0001 (4)0.0023 (5)
N10.0513 (7)0.0516 (7)0.0481 (7)0.0059 (5)0.0045 (5)0.0044 (5)
N20.0534 (7)0.0626 (8)0.0502 (7)0.0063 (6)0.0048 (5)0.0014 (6)
N30.0551 (8)0.0633 (8)0.0504 (7)0.0067 (6)0.0079 (6)0.0093 (6)
N40.0513 (8)0.0972 (11)0.0539 (8)0.0039 (7)0.0041 (6)0.0109 (8)
C10.0393 (7)0.0518 (8)0.0483 (8)0.0061 (6)0.0054 (6)0.0019 (6)
C20.0581 (10)0.0767 (11)0.0537 (9)0.0102 (8)0.0025 (7)0.0089 (8)
C30.0664 (11)0.0779 (12)0.0808 (13)0.0014 (9)0.0035 (9)0.0269 (10)
C40.0601 (11)0.0535 (9)0.1059 (15)0.0060 (8)0.0120 (10)0.0131 (10)
C50.0478 (9)0.0560 (9)0.0763 (11)0.0046 (7)0.0099 (8)0.0109 (8)
C60.0363 (7)0.0531 (8)0.0519 (8)0.0043 (6)0.0043 (6)0.0029 (7)
C70.0517 (9)0.0560 (9)0.0581 (9)0.0022 (7)0.0006 (7)0.0056 (8)
C80.0681 (10)0.0589 (9)0.0552 (9)0.0115 (8)0.0159 (7)0.0147 (7)
C90.0603 (9)0.0606 (9)0.0428 (8)0.0094 (7)0.0016 (6)0.0088 (7)
C100.0538 (9)0.0589 (9)0.0596 (9)0.0123 (7)0.0088 (7)0.0072 (7)
C110.0832 (12)0.0529 (9)0.0697 (11)0.0036 (8)0.0213 (9)0.0057 (8)
C120.0455 (9)0.0941 (13)0.0614 (10)0.0101 (9)0.0062 (7)0.0211 (10)
C130.0492 (8)0.0545 (8)0.0417 (7)0.0029 (6)0.0042 (6)0.0126 (6)
C140.0519 (9)0.0659 (10)0.0548 (9)0.0077 (7)0.0002 (7)0.0070 (8)
C150.0500 (9)0.0853 (12)0.0611 (10)0.0053 (8)0.0070 (7)0.0097 (9)
C160.0710 (11)0.0786 (11)0.0503 (9)0.0176 (9)0.0100 (8)0.0062 (8)
C170.0765 (12)0.0698 (10)0.0404 (8)0.0019 (8)0.0026 (7)0.0030 (7)
C180.0502 (9)0.0674 (10)0.0399 (7)0.0019 (7)0.0030 (6)0.0141 (7)
O1W0.0548 (8)0.1017 (10)0.0759 (9)0.0040 (7)0.0161 (6)0.0099 (8)
Geometric parameters (Å, º) top
O1—C91.4070 (16)C8—C91.502 (2)
O1—C101.4123 (17)C8—H8A0.970
N1—C71.3551 (18)C8—H8B0.970
N1—C11.3790 (17)C9—H9A0.970
N1—C81.4580 (18)C9—H9B0.970
N2—C71.3069 (19)C10—C111.501 (2)
N2—C61.3932 (18)C10—H10A0.970
N3—C121.357 (2)C10—H10B0.970
N3—C131.3770 (18)C11—H11A0.970
N3—C111.454 (2)C11—H11B0.970
N4—C121.308 (2)C12—H12A0.930
N4—C181.3937 (18)C13—C141.389 (2)
C1—C21.388 (2)C13—C181.396 (2)
C1—C61.3994 (18)C14—C151.367 (2)
C2—C31.369 (2)C14—H14A0.930
C2—H2B0.930C15—C161.387 (2)
C3—C41.391 (2)C15—H15A0.930
C3—H3A0.930C16—C171.374 (2)
C4—C51.376 (2)C16—H16A0.930
C4—H4B0.930C17—C181.394 (2)
C5—C61.395 (2)C17—H17A0.930
C5—H5A0.930O1W—H1W10.90 (2)
C7—H7A0.930O1W—H2W10.90 (3)
C9—O1—C10113.87 (11)C8—C9—H9A110.2
C7—N1—C1106.27 (11)O1—C9—H9B110.2
C7—N1—C8126.46 (13)C8—C9—H9B110.2
C1—N1—C8126.78 (12)H9A—C9—H9B108.5
C7—N2—C6104.13 (12)O1—C10—C11107.75 (13)
C12—N3—C13105.97 (13)O1—C10—H10A110.2
C12—N3—C11127.64 (14)C11—C10—H10A110.2
C13—N3—C11126.33 (13)O1—C10—H10B110.2
C12—N4—C18103.97 (13)C11—C10—H10B110.2
N1—C1—C2131.92 (14)H10A—C10—H10B108.5
N1—C1—C6105.38 (12)N3—C11—C10112.84 (13)
C2—C1—C6122.70 (14)N3—C11—H11A109.0
C3—C2—C1116.61 (16)C10—C11—H11A109.0
C3—C2—H2B121.7N3—C11—H11B109.0
C1—C2—H2B121.7C10—C11—H11B109.0
C2—C3—C4121.62 (16)H11A—C11—H11B107.8
C2—C3—H3A119.2N4—C12—N3114.50 (14)
C4—C3—H3A119.2N4—C12—H12A122.8
C5—C4—C3122.03 (16)N3—C12—H12A122.8
C5—C4—H4B119.0N3—C13—C14131.58 (14)
C3—C4—H4B119.0N3—C13—C18105.72 (13)
C4—C5—C6117.43 (16)C14—C13—C18122.69 (13)
C4—C5—H5A121.3C15—C14—C13116.40 (15)
C6—C5—H5A121.3C15—C14—H14A121.8
N2—C6—C5130.57 (14)C13—C14—H14A121.8
N2—C6—C1109.83 (12)C14—C15—C16121.95 (15)
C5—C6—C1119.60 (14)C14—C15—H15A119.0
N2—C7—N1114.39 (13)C16—C15—H15A119.0
N2—C7—H7A122.8C17—C16—C15121.77 (15)
N1—C7—H7A122.8C17—C16—H16A119.1
N1—C8—C9111.94 (12)C15—C16—H16A119.1
N1—C8—H8A109.2C16—C17—C18117.62 (15)
C9—C8—H8A109.2C16—C17—H17A121.2
N1—C8—H8B109.2C18—C17—H17A121.2
C9—C8—H8B109.2N4—C18—C17130.58 (15)
H8A—C8—H8B107.9N4—C18—C13109.83 (13)
O1—C9—C8107.63 (12)C17—C18—C13119.56 (14)
O1—C9—H9A110.2H1W1—O1W—H2W1104 (2)
C7—N1—C1—C2179.35 (14)C9—O1—C10—C11174.41 (12)
C8—N1—C1—C28.3 (2)C12—N3—C11—C1091.23 (18)
C7—N1—C1—C60.45 (14)C13—N3—C11—C1085.57 (17)
C8—N1—C1—C6172.83 (12)O1—C10—C11—N365.81 (16)
N1—C1—C2—C3179.73 (15)C18—N4—C12—N30.08 (17)
C6—C1—C2—C31.0 (2)C13—N3—C12—N40.22 (17)
C1—C2—C3—C40.4 (2)C11—N3—C12—N4177.10 (14)
C2—C3—C4—C50.4 (3)C12—N3—C13—C14179.33 (14)
C3—C4—C5—C60.6 (2)C11—N3—C13—C142.0 (2)
C7—N2—C6—C5179.96 (14)C12—N3—C13—C180.42 (14)
C7—N2—C6—C10.19 (14)C11—N3—C13—C18176.95 (13)
C4—C5—C6—N2179.69 (14)N3—C13—C14—C15177.67 (14)
C4—C5—C6—C10.1 (2)C18—C13—C14—C151.1 (2)
N1—C1—C6—N20.41 (14)C13—C14—C15—C160.2 (2)
C2—C1—C6—N2179.44 (12)C14—C15—C16—C170.7 (2)
N1—C1—C6—C5179.80 (12)C15—C16—C17—C180.7 (2)
C2—C1—C6—C50.8 (2)C12—N4—C18—C17177.84 (15)
C6—N2—C7—N10.11 (16)C12—N4—C18—C130.36 (16)
C1—N1—C7—N20.37 (16)C16—C17—C18—N4178.23 (14)
C8—N1—C7—N2172.78 (13)C16—C17—C18—C130.2 (2)
C7—N1—C8—C980.84 (18)N3—C13—C18—N40.49 (15)
C1—N1—C8—C990.05 (17)C14—C13—C18—N4179.52 (13)
C10—O1—C9—C8173.02 (12)N3—C13—C18—C17177.94 (12)
N1—C8—C9—O164.56 (17)C14—C13—C18—C171.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···N40.90 (2)2.10 (2)2.962 (2)161 (2)
O1W—H2W1···N20.90 (3)2.15 (3)3.021 (2)165 (3)
C12—H12A···O1Wi0.932.443.352 (2)168
Symmetry code: (i) x, y+1, z+1.
 

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