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ISSN: 2056-9890

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

aMicroscale Science Institute, Biology Department, Weifang University, Weifang 261061, People's Republic of China, and bMicrosale Science Institute, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: ffjian2008@163.com

(Received 29 October 2009; accepted 2 November 2009; online 11 November 2009)

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[Lv, F. T. (1998). Chem. Agent. 20, 179.]).

[Scheme 1]

Experimental

Crystal data
  • C7H7N2+·C8H5Cl2O3·H2O

  • Mr = 357.18

  • Orthorhombic, P n a 21

  • 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)

  • Rint = 0.069

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1784 Friedel pairs

  • Flack parameter: 0.04 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O2i 0.86 1.78 2.636 (3) 179
N2—H2A⋯O3 0.86 1.81 2.667 (3) 172
O1W—H1WA⋯O3 0.74 (5) 2.11 (5) 2.822 (4) 160 (5)
O1W—H1WB⋯O1Wii 0.81 (4) 1.95 (4) 2.751 (4) 173 (4)
Symmetry codes: (i) [-x+1, -y+1, z-{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
Benzimidazolium 2-(2,4-dichlorophenoxy)acetate monohydrate top
Crystal data top
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 top
Bruker SMART CCD
diffractometer
3083 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Graphite monochromatorθmax = 27.5°, θmin = 3.4°
ω scansh = 66
13995 measured reflectionsk = 3030
3746 independent reflectionsl = 1818
Refinement top
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) = 0.102 w = 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 methodsAbsolute structure parameter: 0.04 (5)
Crystal data top
C7H7N2+·C8H5Cl2O3·H2OV = 1635.9 (6) Å3
Mr = 357.18Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 4.9322 (10) ŵ = 0.42 mm1
b = 23.808 (5) ÅT = 293 K
c = 13.931 (3) Å0.20 × 0.15 × 0.11 mm
Data collection top
Bruker SMART CCD
diffractometer
3083 reflections with I > 2σ(I)
13995 measured reflectionsRint = 0.069
3746 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102Δρmax = 0.32 e Å3
S = 0.98Δρmin = 0.34 e Å3
3746 reflectionsAbsolute structure: Flack (1983), 1784 Friedel pairs
216 parametersAbsolute structure parameter: 0.04 (5)
1 restraint
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
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)
H2A0.64770.58480.33580.052*
O30.8577 (4)0.60800 (8)0.23670 (12)0.0495 (5)
N10.3939 (4)0.53553 (8)0.51242 (16)0.0424 (5)
H1A0.37160.51050.55630.051*
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)
H13A0.71660.66290.04330.047*
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)
H14A1.23130.57240.10720.046*
H14B1.09830.63090.08670.046*
C70.5692 (5)0.53288 (10)0.4412 (2)0.0446 (6)
H7A0.68880.50330.43100.054*
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)
H2B0.32380.68310.34150.062*
C40.0475 (6)0.66061 (14)0.5315 (3)0.0641 (8)
H4A0.18310.67800.56710.077*
C50.0468 (6)0.60888 (13)0.5602 (2)0.0511 (7)
H5A0.02240.59060.61390.061*
C30.0547 (7)0.68769 (13)0.4503 (3)0.0673 (9)
H3A0.01610.72250.43310.081*
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) top
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, º) top
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, º) top
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, z1/2; (ii) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC7H7N2+·C8H5Cl2O3·H2O
Mr357.18
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)293
a, b, c (Å)4.9322 (10), 23.808 (5), 13.931 (3)
V3)1635.9 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.42
Crystal size (mm)0.20 × 0.15 × 0.11
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13995, 3746, 3083
Rint0.069
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.102, 0.98
No. of reflections3746
No. of parameters216
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.34
Absolute structureFlack (1983), 1784 Friedel pairs
Absolute structure parameter0.04 (5)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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, z1/2; (ii) x+1/2, y+3/2, z.
 

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationLv, F. T. (1998). Chem. Agent. 20, 179.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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