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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3043.
Published online 2009 November 11. doi:  10.1107/S1600536809045899
PMCID: PMC2972003

Benzimidazolium 2-(2,4-dichloro­phen­oxy)acetate monohydrate

Abstract

In the crystal of the title hydrated mol­ecular salt, C7H7N2 +·C8H5Cl2O3·H2O, the components inter­act by way of N—H(...)O and O—H(...)O hydrogen bonds, leading to chains propagating in [100].

Related literature

For background to 2,4-dichloro­phenoxy­acetic acid, see: Lv (1998 [triangle]).

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Object name is e-65-o3043-scheme1.jpg

Experimental

Crystal data

  • C7H7N2 +·C8H5Cl2O3 ·H2O
  • M r = 357.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3043-efi1.jpg
  • a = 4.9322 (10) Å
  • b = 23.808 (5) Å
  • c = 13.931 (3) Å
  • V = 1635.9 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.42 mm−1
  • T = 293 K
  • 0.20 × 0.15 × 0.11 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 13995 measured reflections
  • 3746 independent reflections
  • 3083 reflections with I > 2σ(I)
  • R int = 0.069

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.102
  • S = 0.98
  • 3746 reflections
  • 216 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.34 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1784 Friedel pairs
  • Flack parameter: 0.04 (5)

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045899/hb5201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045899/hb5201Isup2.hkl

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

supplementary crystallographic information

Experimental

A mixture of 2,4-Dichlorophenoxyacetic acid 4.42 g (0.02 mol) and benzimidazole 2.4 g (0.02 mol) was stirred with ethanol (50 ml) at 367 K for 3 h. Colourless bars of (I) were obtained by recrystallization from acetone and ethanol (1:1) at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H and N—H distances of 0.93–0.96 and 0.86 Å, and with Uiso=1.2–1.5Ueq.

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C7H7N2+·C8H5Cl2O3·H2OF(000) = 736
Mr = 357.18Dx = 1.450 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2216 reflections
a = 4.9322 (10) Åθ = 3.4–27.5°
b = 23.808 (5) ŵ = 0.42 mm1
c = 13.931 (3) ÅT = 293 K
V = 1635.9 (6) Å3Bar, colorless
Z = 40.20 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer3083 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
graphiteθmax = 27.5°, θmin = 3.4°
ω scansh = −6→6
13995 measured reflectionsk = −30→30
3746 independent reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
3746 reflectionsΔρmax = 0.32 e Å3
216 parametersΔρmin = −0.34 e Å3
1 restraintAbsolute structure: Flack (1983), 1784 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (5)

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
Cl10.90454 (14)0.52904 (3)0.19850 (5)0.05295 (18)
Cl20.18254 (15)0.69703 (3)0.23025 (7)0.0655 (2)
O10.9973 (3)0.57283 (7)0.00727 (12)0.0399 (4)
N20.5521 (4)0.57806 (9)−0.38610 (16)0.0433 (5)
H2A0.64770.5848−0.33580.052*
O30.8577 (4)0.60800 (8)−0.23670 (12)0.0495 (5)
N10.3939 (4)0.53553 (8)−0.51242 (16)0.0424 (5)
H1A0.37160.5105−0.55630.051*
O20.6808 (3)0.53999 (7)−0.14827 (13)0.0419 (4)
C100.5471 (5)0.61429 (10)0.2019 (2)0.0429 (5)
H10A0.50200.60180.26310.051*
C150.8470 (4)0.57845 (8)−0.16206 (16)0.0316 (4)
C130.6758 (5)0.65057 (10)0.01831 (19)0.0392 (5)
H13A0.71660.6629−0.04330.047*
C10.3528 (5)0.61244 (10)−0.42408 (17)0.0378 (5)
C80.8059 (4)0.60339 (9)0.05484 (16)0.0345 (5)
C141.0646 (5)0.59077 (11)−0.08771 (18)0.0387 (5)
H14A1.23130.5724−0.10720.046*
H14B1.09830.6309−0.08670.046*
C70.5692 (5)0.53288 (10)−0.4412 (2)0.0446 (6)
H7A0.68880.5033−0.43100.054*
C110.4222 (5)0.66116 (11)0.1635 (2)0.0437 (6)
C120.4859 (5)0.67944 (11)0.0727 (2)0.0450 (6)
H12A0.40160.71120.04770.054*
C60.2510 (5)0.58563 (10)−0.50448 (18)0.0360 (5)
C90.7402 (5)0.58614 (10)0.14810 (17)0.0366 (5)
C20.2556 (6)0.66476 (10)−0.3953 (2)0.0517 (7)
H2B0.32380.6831−0.34150.062*
C4−0.0475 (6)0.66061 (14)−0.5315 (3)0.0641 (8)
H4A−0.18310.6780−0.56710.077*
C50.0468 (6)0.60888 (13)−0.5602 (2)0.0511 (7)
H5A−0.02240.5906−0.61390.061*
C30.0547 (7)0.68769 (13)−0.4503 (3)0.0673 (9)
H3A−0.01610.7225−0.43310.081*
O1W0.8508 (6)0.72439 (12)−0.1984 (3)0.0798 (9)
H1WA0.831 (9)0.696 (2)−0.219 (4)0.111 (19)*
H1WB0.995 (8)0.7405 (17)−0.194 (3)0.088 (14)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0616 (4)0.0589 (4)0.0383 (3)0.0105 (3)−0.0035 (3)0.0137 (3)
Cl20.0578 (4)0.0584 (4)0.0802 (6)0.0021 (3)0.0287 (4)−0.0082 (4)
O10.0435 (9)0.0492 (9)0.0271 (8)0.0090 (7)−0.0022 (7)0.0020 (7)
N20.0522 (12)0.0432 (11)0.0344 (11)−0.0106 (10)−0.0063 (9)0.0002 (9)
O30.0647 (12)0.0488 (10)0.0350 (9)−0.0190 (8)−0.0114 (8)0.0130 (7)
N10.0489 (11)0.0373 (10)0.0410 (12)−0.0052 (9)−0.0017 (10)−0.0081 (9)
O20.0464 (10)0.0415 (9)0.0378 (9)−0.0093 (7)−0.0024 (8)0.0054 (7)
C100.0419 (12)0.0494 (13)0.0373 (12)−0.0089 (10)0.0023 (12)−0.0011 (11)
C150.0352 (10)0.0321 (10)0.0274 (11)0.0031 (8)0.0026 (9)−0.0011 (8)
C130.0471 (12)0.0393 (11)0.0313 (12)−0.0005 (10)−0.0020 (10)0.0019 (10)
C10.0457 (12)0.0354 (11)0.0321 (12)−0.0084 (10)0.0051 (10)0.0021 (9)
C80.0356 (11)0.0380 (11)0.0300 (11)−0.0005 (9)−0.0054 (10)−0.0027 (9)
C140.0354 (12)0.0497 (13)0.0310 (11)0.0018 (10)−0.0023 (10)0.0029 (10)
C70.0502 (14)0.0363 (12)0.0474 (15)−0.0031 (10)−0.0030 (12)−0.0002 (11)
C110.0376 (12)0.0434 (13)0.0501 (15)−0.0058 (10)0.0041 (11)−0.0061 (11)
C120.0462 (13)0.0397 (12)0.0491 (16)0.0029 (10)−0.0018 (12)0.0007 (11)
C60.0377 (12)0.0382 (11)0.0322 (12)−0.0057 (9)0.0012 (9)0.0008 (9)
C90.0391 (11)0.0419 (12)0.0288 (12)−0.0036 (10)−0.0022 (10)0.0019 (9)
C20.0674 (17)0.0394 (14)0.0482 (16)−0.0074 (13)0.0174 (14)−0.0081 (12)
C40.0554 (16)0.0667 (19)0.070 (2)0.0127 (14)0.0073 (16)0.0225 (17)
C50.0493 (14)0.0633 (18)0.0409 (15)−0.0074 (13)−0.0075 (13)0.0076 (13)
C30.078 (2)0.0415 (15)0.083 (3)0.0100 (14)0.023 (2)0.0027 (16)
O1W0.0654 (16)0.0463 (13)0.128 (3)0.0020 (12)0.0147 (17)0.0039 (14)

Geometric parameters (Å, °)

Cl1—C91.731 (2)C1—C61.384 (3)
Cl2—C111.729 (3)C1—C21.394 (3)
O1—C81.364 (3)C8—C91.401 (3)
O1—C141.429 (3)C14—H14A0.9700
N2—C71.324 (3)C14—H14B0.9700
N2—C11.384 (3)C7—H7A0.9300
N2—H2A0.8600C11—C121.375 (4)
O3—C151.257 (3)C12—H12A0.9300
N1—C71.318 (3)C6—C51.387 (4)
N1—C61.390 (3)C2—C31.366 (4)
N1—H1A0.8600C2—H2B0.9300
O2—C151.244 (3)C4—C51.376 (4)
C10—C111.383 (4)C4—C31.396 (5)
C10—C91.385 (3)C4—H4A0.9300
C10—H10A0.9300C5—H5A0.9300
C15—C141.520 (3)C3—H3A0.9300
C13—C121.387 (3)O1W—H1WA0.73 (5)
C13—C81.390 (3)O1W—H1WB0.81 (4)
C13—H13A0.9300
C8—O1—C14116.82 (18)N1—C7—N2110.9 (2)
C7—N2—C1107.7 (2)N1—C7—H7A124.6
C7—N2—H2A126.2N2—C7—H7A124.6
C1—N2—H2A126.2C12—C11—C10120.7 (3)
C7—N1—C6108.3 (2)C12—C11—Cl2119.7 (2)
C7—N1—H1A125.9C10—C11—Cl2119.7 (2)
C6—N1—H1A125.9C11—C12—C13120.0 (2)
C11—C10—C9119.2 (3)C11—C12—H12A120.0
C11—C10—H10A120.4C13—C12—H12A120.0
C9—C10—H10A120.4C1—C6—C5122.2 (2)
O2—C15—O3124.6 (2)C1—C6—N1106.0 (2)
O2—C15—C14120.1 (2)C5—C6—N1131.8 (2)
O3—C15—C14115.25 (19)C10—C9—C8121.3 (2)
C12—C13—C8120.8 (2)C10—C9—Cl1118.83 (19)
C12—C13—H13A119.6C8—C9—Cl1119.89 (18)
C8—C13—H13A119.6C3—C2—C1116.4 (3)
N2—C1—C6107.1 (2)C3—C2—H2B121.8
N2—C1—C2131.5 (2)C1—C2—H2B121.8
C6—C1—C2121.4 (2)C5—C4—C3121.8 (3)
O1—C8—C13124.9 (2)C5—C4—H4A119.1
O1—C8—C9117.0 (2)C3—C4—H4A119.1
C13—C8—C9118.0 (2)C4—C5—C6116.1 (3)
O1—C14—C15114.17 (19)C4—C5—H5A122.0
O1—C14—H14A108.7C6—C5—H5A122.0
C15—C14—H14A108.7C2—C3—C4122.1 (3)
O1—C14—H14B108.7C2—C3—H3A118.9
C15—C14—H14B108.7C4—C3—H3A118.9
H14A—C14—H14B107.6H1WA—O1W—H1WB126 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.861.782.636 (3)179
N2—H2A···O30.861.812.667 (3)172
O1W—H1WA···O30.74 (5)2.11 (5)2.822 (4)160 (5)
O1W—H1WB···O1Wii0.81 (4)1.95 (4)2.751 (4)173 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5201).

References

  • Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Lv, F. T. (1998). Chem. Agent. 20, 179.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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