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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o674.
Published online 2008 March 5. doi:  10.1107/S1600536808005916
PMCID: PMC2960975

Bis(benzimidazolium) naphthalene-1,5-disulfonate trihydrate

Abstract

The title compound, 2C7H7N2 +·C10H6O6S2 2−·3H2O, consists of two crystallographically independent benzimidazolium cations, two independent naphthalene-1,5-disulfonate dianions (both generated by inversion) and three water mol­ecules. These components construct an infinite three-dimensional framework in the crystal structure via O—H(...)O and N—H(...)O hydrogen bonds.

Related literature

For related literature, see: Wang & Wei (2007 [triangle]).

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Object name is e-64-0o674-scheme1.jpg

Experimental

Crystal data

  • 2C7H7N2 +·C10H6O6S2 2−·3H2O
  • M r = 578.61
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o674-efi1.jpg
  • a = 8.372 (4) Å
  • b = 9.889 (5) Å
  • c = 17.044 (8) Å
  • α = 80.914 (8)°
  • β = 87.557 (9)°
  • γ = 73.641 (8)°
  • V = 1337.0 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 296 (2) K
  • 0.15 × 0.12 × 0.04 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.962, T max = 0.990
  • 6891 measured reflections
  • 4670 independent reflections
  • 3494 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.110
  • S = 1.06
  • 4670 reflections
  • 392 parameters
  • 37 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005916/hb2700sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005916/hb2700Isup2.hkl

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

supplementary crystallographic information

Comment

This work continues our previous synthetic and structural studies of supramolecular interactions in aromatic molecular salts and adducts (Wang & Wei, 2007). Herein we report the structure of the title salt, (I).

The title compound (I) contains two independent benzimidazolium cations, two naphthalene-1,5-disulfonate dianions and three water molecules (Fig. 1). Each of the dianions occupies a special position on an inversion centre. Therefore, the asymmetric unit of the crystal structure is composed of two half naphthalene-1,5-disulfonate dianions, two benzimidazolium cations and three water molecules.

These ions and molecules are finally organized into an infinite three-dimensional framework through N—H···O and O—H···O hydrogen bonds (Fig. 2 and Table 1).

Experimental

A 5-ml ethanol solution of benzimidazole (1.00 mmol, 0.118 g) was added to an aqueous solution (25 ml) of naphthalene-1,5-disulfonic acid (0.50 mmol, 0.15 g). The mixture was stirred for 10 minutes at 373 K. The solution was filtered, and the filtrate was allowed to stand at room temperature. After several days, colourless blocks of (I) were recovered.

Refinement

The H atoms bonded to N and O were located in a difference map and refined with distance restraints [N—H = 0.90 (1) Å, water O—H = 0.85 (1)Å and H···H = 1.34 (1) Å]; their Uiso values were freely refined.

The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. Unlabeled atoms in the C8 anion are related to labeled atoms by (1 - x, 1 - y, 1 - z). Unlabeled ...
Fig. 2.
The crystal packing of (I). Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in hydrogen bonds are omitted.

Crystal data

2C7H7N2+·C10H6O6S22–·3H2OZ = 2
Mr = 578.61F000 = 604
Triclinic, P1Dx = 1.437 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.372 (4) ÅCell parameters from 3010 reflections
b = 9.889 (5) Åθ = 2.5–28.2º
c = 17.044 (8) ŵ = 0.26 mm1
α = 80.914 (8)ºT = 296 (2) K
β = 87.557 (9)ºBlock, colourless
γ = 73.641 (8)º0.15 × 0.12 × 0.04 mm
V = 1337.0 (11) Å3

Data collection

Bruker SMART APEX CCD diffractometer4670 independent reflections
Radiation source: fine-focus sealed tube3494 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 296(2) Kθmax = 25.0º
ω scansθmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −9→6
Tmin = 0.962, Tmax = 0.990k = −11→10
6891 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.0559P)2 + 0.0198P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
4670 reflectionsΔρmax = 0.30 e Å3
392 parametersΔρmin = −0.33 e Å3
37 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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 (Å2)

xyzUiso*/Ueq
S10.75176 (8)0.65881 (6)0.37087 (4)0.04129 (19)
S20.39100 (7)0.25493 (6)0.14588 (3)0.03710 (17)
N10.8368 (3)0.0653 (2)1.09595 (14)0.0502 (6)
H1A0.794 (4)−0.007 (2)1.1155 (19)0.098 (12)*
N20.9885 (3)0.2131 (2)1.08427 (15)0.0505 (6)
H2A1.065 (3)0.253 (3)1.0965 (18)0.082 (11)*
N30.0749 (3)0.7339 (2)0.48285 (14)0.0460 (5)
H3A0.032 (3)0.670 (2)0.4660 (15)0.063 (9)*
N40.1689 (3)0.8418 (2)0.56460 (12)0.0432 (5)
H4A0.192 (3)0.865 (3)0.6108 (9)0.056 (8)*
O10.7659 (2)0.65613 (18)0.28505 (10)0.0554 (5)
O20.6945 (2)0.80262 (17)0.39064 (11)0.0571 (5)
O30.9056 (2)0.57458 (17)0.41288 (10)0.0473 (4)
O40.21223 (19)0.33257 (17)0.14166 (10)0.0457 (4)
O50.4281 (2)0.13448 (16)0.10230 (10)0.0490 (5)
O60.4518 (2)0.21705 (18)0.22760 (10)0.0545 (5)
O70.6702 (3)0.8721 (2)0.15255 (12)0.0636 (6)
H7A0.695 (3)0.822 (3)0.1982 (9)0.072 (5)*
H7B0.575 (2)0.928 (3)0.1601 (16)0.096 (14)*
O80.7493 (3)0.0547 (2)0.30528 (12)0.0573 (5)
H8A0.733 (3)−0.0213 (17)0.3299 (15)0.067 (5)*
H8B0.657 (2)0.102 (3)0.283 (2)0.130 (17)*
O90.0253 (4)0.6345 (3)0.73328 (16)0.0971 (8)
H9A−0.066 (2)0.618 (3)0.719 (2)0.081 (5)*
H9B0.089 (3)0.5484 (16)0.743 (2)0.101 (6)*
C10.9359 (3)0.1177 (3)1.13375 (17)0.0546 (7)
H10.96410.09121.18730.065*
C20.8228 (3)0.1305 (2)1.01695 (16)0.0421 (6)
C30.7326 (3)0.1173 (3)0.95341 (18)0.0548 (7)
H30.66750.05410.95850.066*
C40.7446 (4)0.2034 (3)0.88195 (18)0.0619 (8)
H40.68610.19750.83800.074*
C50.8424 (4)0.2990 (3)0.87418 (18)0.0626 (8)
H50.84680.35470.82520.075*
C60.9320 (3)0.3128 (3)0.93678 (17)0.0532 (7)
H60.99670.37630.93140.064*
C70.9205 (3)0.2262 (2)1.00908 (16)0.0428 (6)
C80.4007 (3)0.4475 (3)0.37232 (15)0.0514 (7)
H80.34770.41860.33380.062*
C90.5171 (3)0.5243 (3)0.34934 (15)0.0455 (6)
H90.54100.54520.29570.055*
C100.5963 (3)0.5689 (2)0.40503 (13)0.0360 (5)
C110.5595 (3)0.5398 (2)0.48859 (13)0.0348 (5)
C120.6357 (3)0.5851 (3)0.54888 (14)0.0442 (6)
H120.71140.63780.53460.053*
C130.0892 (3)0.7450 (3)0.55844 (16)0.0478 (7)
H130.04930.69270.60110.057*
C140.1487 (3)0.8290 (2)0.43592 (14)0.0392 (6)
C150.1657 (3)0.8615 (3)0.35337 (16)0.0541 (7)
H150.12640.81540.31810.065*
C160.2444 (4)0.9660 (3)0.32755 (17)0.0620 (8)
H160.25840.99070.27330.074*
C170.3036 (3)1.0360 (3)0.38033 (18)0.0578 (8)
H170.35521.10600.36010.069*
C180.2877 (3)1.0043 (3)0.46113 (16)0.0477 (6)
H180.32741.05070.49600.057*
C190.2086 (3)0.8982 (2)0.48839 (14)0.0369 (6)
C200.6767 (3)0.5287 (2)0.11047 (14)0.0394 (6)
H200.74860.55480.14140.047*
C210.6018 (3)0.4208 (2)0.14309 (13)0.0357 (5)
H210.62490.37640.19530.043*
C220.4946 (3)0.3809 (2)0.09785 (13)0.0308 (5)
C230.4614 (3)0.4453 (2)0.01605 (12)0.0288 (5)
C240.3560 (3)0.4050 (2)−0.03388 (13)0.0353 (5)
H240.30840.3323−0.01390.042*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0484 (4)0.0338 (3)0.0428 (4)−0.0151 (3)−0.0003 (3)−0.0022 (3)
S20.0385 (4)0.0360 (3)0.0376 (3)−0.0162 (3)0.0002 (3)0.0027 (3)
N10.0443 (13)0.0410 (13)0.0639 (16)−0.0139 (11)0.0030 (11)−0.0011 (11)
N20.0383 (13)0.0498 (14)0.0660 (16)−0.0161 (11)−0.0060 (11)−0.0082 (12)
N30.0469 (13)0.0372 (12)0.0571 (15)−0.0157 (10)−0.0011 (11)−0.0087 (11)
N40.0488 (13)0.0396 (12)0.0397 (13)−0.0117 (10)−0.0042 (10)−0.0018 (10)
O10.0689 (13)0.0589 (12)0.0399 (10)−0.0246 (10)0.0042 (9)−0.0003 (9)
O20.0714 (13)0.0312 (9)0.0693 (13)−0.0159 (9)0.0042 (10)−0.0072 (9)
O30.0444 (10)0.0422 (10)0.0567 (11)−0.0170 (8)−0.0044 (8)−0.0020 (8)
O40.0346 (10)0.0478 (10)0.0541 (11)−0.0140 (8)0.0058 (8)−0.0033 (8)
O50.0555 (11)0.0317 (9)0.0634 (12)−0.0180 (8)0.0009 (9)−0.0069 (8)
O60.0642 (12)0.0609 (12)0.0395 (10)−0.0306 (10)−0.0067 (9)0.0153 (8)
O70.0655 (15)0.0497 (13)0.0740 (15)−0.0202 (12)−0.0078 (11)0.0045 (10)
O80.0676 (14)0.0493 (12)0.0582 (13)−0.0246 (11)−0.0130 (11)0.0009 (10)
O90.109 (2)0.0876 (17)0.0720 (16)0.0001 (16)0.0210 (16)−0.0007 (14)
C10.0467 (17)0.0544 (17)0.0579 (18)−0.0094 (14)−0.0031 (14)−0.0022 (14)
C20.0341 (14)0.0358 (14)0.0562 (17)−0.0083 (11)0.0035 (12)−0.0099 (12)
C30.0445 (16)0.0523 (17)0.074 (2)−0.0178 (13)0.0072 (14)−0.0234 (15)
C40.0578 (19)0.069 (2)0.061 (2)−0.0145 (16)−0.0041 (15)−0.0214 (16)
C50.065 (2)0.0580 (19)0.0579 (19)−0.0107 (16)0.0059 (16)−0.0032 (15)
C60.0507 (17)0.0434 (15)0.0679 (19)−0.0184 (13)0.0076 (15)−0.0078 (14)
C70.0331 (14)0.0369 (14)0.0585 (17)−0.0084 (11)0.0032 (12)−0.0112 (12)
C80.0587 (17)0.0617 (17)0.0434 (16)−0.0275 (15)−0.0076 (13)−0.0147 (13)
C90.0541 (16)0.0511 (15)0.0341 (13)−0.0175 (13)−0.0024 (12)−0.0087 (12)
C100.0384 (14)0.0325 (12)0.0363 (13)−0.0083 (10)−0.0013 (11)−0.0054 (10)
C110.0360 (13)0.0296 (12)0.0400 (13)−0.0095 (10)−0.0027 (10)−0.0074 (10)
C120.0474 (15)0.0487 (15)0.0441 (15)−0.0229 (13)−0.0004 (12)−0.0118 (12)
C130.0498 (16)0.0364 (14)0.0532 (17)−0.0104 (12)0.0041 (13)0.0014 (12)
C140.0350 (13)0.0358 (13)0.0450 (15)−0.0080 (11)0.0009 (11)−0.0047 (11)
C150.0566 (18)0.0572 (17)0.0471 (16)−0.0108 (14)−0.0004 (13)−0.0130 (13)
C160.067 (2)0.068 (2)0.0452 (17)−0.0154 (17)0.0105 (15)−0.0002 (15)
C170.0546 (18)0.0537 (17)0.0628 (19)−0.0193 (15)0.0120 (15)0.0027 (15)
C180.0410 (15)0.0443 (15)0.0606 (18)−0.0165 (12)0.0006 (13)−0.0074 (13)
C190.0326 (13)0.0336 (13)0.0413 (14)−0.0058 (11)−0.0028 (11)−0.0020 (11)
C200.0410 (14)0.0432 (14)0.0399 (14)−0.0193 (12)−0.0071 (11)−0.0076 (11)
C210.0407 (14)0.0372 (13)0.0294 (12)−0.0121 (11)−0.0022 (10)−0.0030 (10)
C220.0314 (12)0.0278 (12)0.0329 (12)−0.0079 (10)0.0016 (10)−0.0045 (9)
C230.0276 (12)0.0273 (12)0.0319 (12)−0.0078 (9)0.0037 (10)−0.0062 (10)
C240.0381 (13)0.0343 (13)0.0379 (13)−0.0185 (11)−0.0001 (10)−0.0030 (10)

Geometric parameters (Å, °)

S1—O21.4558 (18)C5—H50.9300
S1—O11.4663 (19)C6—C71.402 (4)
S1—O31.4665 (18)C6—H60.9300
S1—C101.802 (2)C8—C12i1.373 (3)
S2—O51.4555 (18)C8—C91.404 (3)
S2—O61.4586 (18)C8—H80.9300
S2—O41.4761 (18)C9—C101.373 (3)
S2—C221.789 (2)C9—H90.9300
N1—C11.329 (3)C10—C111.445 (3)
N1—C21.393 (3)C11—C121.423 (3)
N1—H1A0.898 (10)C11—C11i1.442 (4)
N2—C11.322 (3)C12—C8i1.373 (3)
N2—C71.397 (3)C12—H120.9300
N2—H2A0.887 (18)C13—H130.9300
N3—C131.323 (3)C14—C191.394 (3)
N3—C141.398 (3)C14—C151.403 (3)
N3—H3A0.895 (10)C15—C161.382 (4)
N4—C131.330 (3)C15—H150.9300
N4—C191.396 (3)C16—C171.401 (4)
N4—H4A0.899 (10)C16—H160.9300
O7—H7A0.853 (10)C17—C181.373 (4)
O7—H7B0.852 (10)C17—H170.9300
O8—H8A0.844 (10)C18—C191.402 (3)
O8—H8B0.847 (10)C18—H180.9300
O9—H9A0.871 (10)C20—C24ii1.367 (3)
O9—H9B0.863 (10)C20—C211.414 (3)
C1—H10.9300C20—H200.9300
C2—C31.389 (4)C21—C221.382 (3)
C2—C71.403 (3)C21—H210.9300
C3—C41.389 (4)C22—C231.442 (3)
C3—H30.9300C23—C241.425 (3)
C4—C51.403 (4)C23—C23ii1.436 (4)
C4—H40.9300C24—C20ii1.367 (3)
C5—C61.375 (4)C24—H240.9300
O2—S1—O1113.02 (11)C9—C8—H8119.7
O2—S1—O3112.36 (11)C10—C9—C8120.8 (2)
O1—S1—O3111.76 (11)C10—C9—H9119.6
O2—S1—C10107.58 (11)C8—C9—H9119.6
O1—S1—C10105.71 (11)C9—C10—C11120.7 (2)
O3—S1—C10105.83 (10)C9—C10—S1117.92 (18)
O5—S2—O6113.58 (11)C11—C10—S1121.33 (17)
O5—S2—O4111.49 (10)C12—C11—C11i118.8 (3)
O6—S2—O4111.78 (11)C12—C11—C10123.3 (2)
O5—S2—C22108.32 (10)C11i—C11—C10117.9 (3)
O6—S2—C22106.06 (10)C8i—C12—C11121.2 (2)
O4—S2—C22105.02 (10)C8i—C12—H12119.4
C1—N1—C2108.7 (2)C11—C12—H12119.4
C1—N1—H1A127 (2)N3—C13—N4110.2 (2)
C2—N1—H1A124 (2)N3—C13—H13124.9
C1—N2—C7109.1 (2)N4—C13—H13124.9
C1—N2—H2A124 (2)C19—C14—N3106.2 (2)
C7—N2—H2A126 (2)C19—C14—C15121.6 (2)
C13—N3—C14108.8 (2)N3—C14—C15132.2 (2)
C13—N3—H3A124.4 (18)C16—C15—C14116.0 (3)
C14—N3—H3A126.6 (18)C16—C15—H15122.0
C13—N4—C19108.6 (2)C14—C15—H15122.0
C13—N4—H4A124.5 (17)C15—C16—C17122.3 (3)
C19—N4—H4A126.9 (17)C15—C16—H16118.9
H7A—O7—H7B103.0 (15)C17—C16—H16118.9
H8A—O8—H8B105.6 (15)C18—C17—C16121.9 (3)
H9A—O9—H9B100.1 (14)C18—C17—H17119.1
N2—C1—N1110.2 (3)C16—C17—H17119.1
N2—C1—H1124.9C17—C18—C19116.6 (3)
N1—C1—H1124.9C17—C18—H18121.7
C3—C2—N1132.0 (2)C19—C18—H18121.7
C3—C2—C7121.6 (2)C14—C19—N4106.3 (2)
N1—C2—C7106.4 (2)C14—C19—C18121.6 (2)
C4—C3—C2116.5 (3)N4—C19—C18132.1 (2)
C4—C3—H3121.8C24ii—C20—C21120.5 (2)
C2—C3—H3121.8C24ii—C20—H20119.7
C3—C4—C5121.9 (3)C21—C20—H20119.7
C3—C4—H4119.1C22—C21—C20120.4 (2)
C5—C4—H4119.1C22—C21—H21119.8
C6—C5—C4122.0 (3)C20—C21—H21119.8
C6—C5—H5119.0C21—C22—C23120.6 (2)
C4—C5—H5119.0C21—C22—S2117.66 (17)
C5—C6—C7116.4 (3)C23—C22—S2121.65 (16)
C5—C6—H6121.8C24—C23—C23ii118.9 (2)
C7—C6—H6121.8C24—C23—C22122.86 (19)
N2—C7—C6132.7 (2)C23ii—C23—C22118.2 (2)
N2—C7—C2105.7 (2)C20ii—C24—C23121.3 (2)
C6—C7—C2121.6 (3)C20ii—C24—H24119.3
C12i—C8—C9120.6 (2)C23—C24—H24119.3
C12i—C8—H8119.7

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O7iii0.898 (10)1.820 (12)2.708 (3)170 (3)
N2—H2A···O4iv0.887 (18)1.885 (19)2.762 (3)170 (3)
N3—H3A···O3v0.895 (10)1.937 (12)2.812 (3)166 (2)
N4—H4A···O8i0.899 (10)1.883 (11)2.771 (3)169 (2)
O7—H7B···O5vi0.852 (10)2.169 (19)2.839 (3)135 (2)
O8—H8A···O2vii0.844 (10)1.982 (10)2.826 (3)178 (3)
O7—H7A···O10.853 (10)1.999 (12)2.823 (3)162 (3)
O8—H8B···O60.847 (10)1.963 (10)2.809 (3)176 (3)
O9—H9B···O1i0.863 (10)2.157 (18)2.970 (3)157 (3)

Symmetry codes: (iii) x, y−1, z+1; (iv) x+1, y, z+1; (v) x−1, y, z; (i) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2700).

References

  • Bruker (2001). SAINT-Plus, SMART and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Wang, Z.-L. & Wei, L.-H. (2007). Acta Cryst. E63, o1448–o1449.

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