The asymmetric unit of the title compound, C7H7N2+·C9H7O5-, consists of one benzimidazolium cation and one 4-carboxyphenoxyacetate anion. A two-dimensional supramolecular hydrogen-bonded network structure is formed via intermolecular hydrogen bonds in the bc plane.
Supporting information
CCDC reference: 294002
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.119
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.33
PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C10 .. 2.99 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Benzimidazolium 3-carboxy-phenoxyacetate
top
Crystal data top
C9H7O5+·C7H7N2− | Z = 2 |
Mr = 314.29 | F(000) = 328 |
Triclinic, P1 | Dx = 1.423 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2371 (14) Å | Cell parameters from 6343 reflections |
b = 9.5895 (19) Å | θ = 3.2–26.2° |
c = 11.633 (2) Å | µ = 0.11 mm−1 |
α = 75.80 (3)° | T = 295 K |
β = 75.50 (3)° | Prism, colourless |
γ = 72.69 (3)° | 0.38 × 0.27 × 0.21 mm |
V = 733.4 (3) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 3099 independent reflections |
Radiation source: fine-focus sealed tube | 2263 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 10 pixels mm-1 | θmax = 26.8°, θmin = 3.0° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −12→12 |
Tmin = 0.966, Tmax = 0.978 | l = −14→14 |
6669 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.1766P] where P = (Fo2 + 2Fc2)/3 |
3099 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.28 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2963 (3) | 0.38926 (14) | 0.51727 (12) | 0.0592 (4) | |
O2 | 0.1953 (2) | 0.63741 (13) | 0.48381 (10) | 0.0426 (3) | |
O3 | 0.14871 (19) | 0.64278 (13) | 0.71980 (10) | 0.0407 (3) | |
O4 | −0.0099 (2) | 0.82520 (17) | 1.23694 (13) | 0.0626 (4) | |
O5 | 0.2097 (2) | 0.60423 (16) | 1.26497 (11) | 0.0534 (4) | |
H19 | 0.195 (4) | 0.618 (3) | 1.3374 (12) | 0.080* | |
N1 | 0.2432 (2) | 0.12506 (16) | 0.50422 (14) | 0.0425 (4) | |
H17 | 0.223 (3) | 0.2084 (16) | 0.5327 (19) | 0.064* | |
N2 | 0.2477 (2) | −0.09988 (16) | 0.49387 (13) | 0.0381 (4) | |
H18 | 0.230 (3) | −0.1919 (14) | 0.5099 (19) | 0.058* | |
C1 | 0.2468 (3) | 0.51070 (18) | 0.55053 (15) | 0.0346 (4) | |
C2 | 0.2614 (3) | 0.50543 (18) | 0.68079 (15) | 0.0366 (4) | |
H2A | 0.2122 | 0.4236 | 0.7337 | 0.044* | |
H2B | 0.3984 | 0.4885 | 0.6858 | 0.044* | |
C3 | 0.1412 (2) | 0.64986 (18) | 0.83817 (14) | 0.0323 (4) | |
C4 | 0.0177 (3) | 0.77946 (19) | 0.87702 (15) | 0.0367 (4) | |
H4 | −0.0554 | 0.8521 | 0.8250 | 0.044* | |
C5 | 0.0045 (3) | 0.79938 (19) | 0.99355 (15) | 0.0365 (4) | |
H5 | −0.0767 | 0.8861 | 1.0187 | 0.044* | |
C6 | 0.1127 (3) | 0.68975 (19) | 1.07417 (14) | 0.0337 (4) | |
C7 | 0.2314 (3) | 0.56003 (19) | 1.03527 (15) | 0.0373 (4) | |
H7 | 0.3013 | 0.4860 | 1.0881 | 0.045* | |
C8 | 0.2474 (3) | 0.53929 (19) | 0.91786 (15) | 0.0379 (4) | |
H8 | 0.3282 | 0.4524 | 0.8928 | 0.046* | |
C9 | 0.0966 (3) | 0.7146 (2) | 1.19957 (15) | 0.0379 (4) | |
C10 | 0.1977 (3) | −0.0007 (2) | 0.56533 (17) | 0.0415 (4) | |
H10 | 0.1391 | −0.0168 | 0.6466 | 0.050* | |
C11 | 0.3334 (2) | −0.03681 (18) | 0.37898 (16) | 0.0345 (4) | |
C12 | 0.4172 (3) | −0.0944 (2) | 0.27285 (18) | 0.0450 (5) | |
H12 | 0.4198 | −0.1904 | 0.2682 | 0.054* | |
C13 | 0.4960 (3) | 0.0004 (3) | 0.17501 (19) | 0.0554 (5) | |
H13 | 0.5539 | −0.0334 | 0.1027 | 0.067* | |
C14 | 0.4911 (3) | 0.1465 (3) | 0.1818 (2) | 0.0583 (6) | |
H14 | 0.5454 | 0.2062 | 0.1138 | 0.070* | |
C15 | 0.4082 (3) | 0.2029 (2) | 0.2861 (2) | 0.0511 (5) | |
H15 | 0.4043 | 0.2994 | 0.2901 | 0.061* | |
C16 | 0.3301 (3) | 0.10790 (18) | 0.38575 (17) | 0.0371 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1064 (12) | 0.0359 (7) | 0.0427 (8) | −0.0235 (8) | −0.0138 (8) | −0.0145 (6) |
O2 | 0.0736 (9) | 0.0327 (6) | 0.0273 (6) | −0.0145 (6) | −0.0164 (6) | −0.0078 (5) |
O3 | 0.0574 (8) | 0.0389 (7) | 0.0254 (6) | −0.0019 (6) | −0.0133 (5) | −0.0121 (5) |
O4 | 0.0797 (11) | 0.0605 (9) | 0.0432 (8) | 0.0081 (8) | −0.0155 (8) | −0.0298 (7) |
O5 | 0.0780 (10) | 0.0517 (8) | 0.0295 (7) | 0.0008 (7) | −0.0195 (7) | −0.0173 (6) |
N1 | 0.0539 (10) | 0.0314 (8) | 0.0471 (9) | −0.0061 (7) | −0.0141 (7) | −0.0174 (7) |
N2 | 0.0479 (9) | 0.0284 (7) | 0.0396 (8) | −0.0085 (7) | −0.0087 (7) | −0.0102 (6) |
C1 | 0.0491 (10) | 0.0323 (9) | 0.0284 (8) | −0.0179 (8) | −0.0053 (7) | −0.0092 (7) |
C2 | 0.0504 (10) | 0.0314 (9) | 0.0294 (9) | −0.0103 (8) | −0.0077 (8) | −0.0078 (7) |
C3 | 0.0374 (9) | 0.0371 (9) | 0.0247 (8) | −0.0103 (8) | −0.0064 (7) | −0.0085 (7) |
C4 | 0.0402 (9) | 0.0364 (9) | 0.0310 (9) | −0.0034 (8) | −0.0100 (7) | −0.0059 (7) |
C5 | 0.0384 (9) | 0.0353 (9) | 0.0347 (9) | −0.0036 (8) | −0.0051 (7) | −0.0132 (7) |
C6 | 0.0397 (9) | 0.0386 (9) | 0.0262 (8) | −0.0142 (8) | −0.0039 (7) | −0.0090 (7) |
C7 | 0.0481 (10) | 0.0362 (9) | 0.0263 (8) | −0.0037 (8) | −0.0132 (7) | −0.0059 (7) |
C8 | 0.0483 (10) | 0.0351 (9) | 0.0293 (9) | −0.0015 (8) | −0.0096 (8) | −0.0127 (7) |
C9 | 0.0463 (10) | 0.0420 (10) | 0.0291 (9) | −0.0129 (9) | −0.0056 (8) | −0.0126 (8) |
C10 | 0.0481 (11) | 0.0379 (10) | 0.0389 (10) | −0.0065 (8) | −0.0093 (8) | −0.0119 (8) |
C11 | 0.0356 (9) | 0.0299 (8) | 0.0396 (9) | −0.0044 (7) | −0.0115 (8) | −0.0094 (7) |
C12 | 0.0454 (11) | 0.0413 (10) | 0.0483 (11) | −0.0034 (9) | −0.0085 (9) | −0.0180 (9) |
C13 | 0.0483 (12) | 0.0710 (15) | 0.0419 (11) | −0.0069 (11) | −0.0023 (9) | −0.0175 (10) |
C14 | 0.0532 (13) | 0.0660 (14) | 0.0523 (13) | −0.0244 (11) | −0.0073 (10) | 0.0037 (11) |
C15 | 0.0564 (12) | 0.0419 (11) | 0.0596 (13) | −0.0203 (10) | −0.0166 (10) | −0.0023 (10) |
C16 | 0.0385 (9) | 0.0306 (9) | 0.0451 (10) | −0.0061 (8) | −0.0142 (8) | −0.0093 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.240 (2) | C11—C16 | 1.402 (2) |
O2—C1 | 1.277 (2) | C12—C13 | 1.386 (3) |
O3—C3 | 1.3819 (19) | C13—C14 | 1.412 (3) |
O3—C2 | 1.440 (2) | C14—C15 | 1.374 (3) |
O4—C9 | 1.217 (2) | C15—C16 | 1.398 (3) |
O5—C9 | 1.330 (2) | O5—H19 | 0.86 (2) |
N1—C10 | 1.329 (2) | N1—H17 | 0.90 (2) |
N1—C16 | 1.392 (2) | N2—H18 | 0.90 (2) |
N2—C10 | 1.326 (2) | C2—H2A | 0.9700 |
N2—C11 | 1.396 (2) | C2—H2B | 0.9700 |
C1—C2 | 1.533 (2) | C4—H4 | 0.9300 |
C3—C4 | 1.400 (2) | C5—H5 | 0.9300 |
C3—C8 | 1.401 (2) | C7—H7 | 0.9300 |
C4—C5 | 1.391 (2) | C8—H8 | 0.9300 |
C5—C6 | 1.411 (2) | C10—H10 | 0.9300 |
C6—C7 | 1.391 (2) | C12—H12 | 0.9300 |
C6—C9 | 1.506 (2) | C13—H13 | 0.9300 |
C7—C8 | 1.400 (2) | C14—H14 | 0.9300 |
C11—C12 | 1.399 (3) | C15—H15 | 0.9300 |
| | | |
C3—O3—C2 | 116.43 (13) | C15—C16—C11 | 121.61 (18) |
C10—N1—C16 | 108.70 (15) | C9—O5—H19 | 112.7 (17) |
C10—N2—C11 | 108.53 (14) | C10—N1—H17 | 126.9 (14) |
O1—C1—O2 | 125.38 (16) | C16—N1—H17 | 124.4 (14) |
O1—C1—C2 | 116.03 (15) | C10—N2—H18 | 129.7 (14) |
O2—C1—C2 | 118.49 (14) | C11—N2—H18 | 121.8 (14) |
O3—C2—C1 | 110.55 (14) | O3—C2—H2A | 109.5 |
O3—C3—C4 | 115.41 (15) | C1—C2—H2A | 109.5 |
O3—C3—C8 | 124.78 (15) | O3—C2—H2B | 109.5 |
C4—C3—C8 | 119.80 (15) | C1—C2—H2B | 109.5 |
C5—C4—C3 | 119.87 (16) | H2A—C2—H2B | 108.1 |
C4—C5—C6 | 120.89 (16) | C5—C4—H4 | 120.1 |
C7—C6—C5 | 118.63 (15) | C3—C4—H4 | 120.1 |
C7—C6—C9 | 121.59 (16) | C4—C5—H5 | 119.6 |
C5—C6—C9 | 119.78 (16) | C6—C5—H5 | 119.6 |
C6—C7—C8 | 121.01 (16) | C6—C7—H7 | 119.5 |
C7—C8—C3 | 119.78 (16) | C8—C7—H7 | 119.5 |
O4—C9—O5 | 123.53 (16) | C7—C8—H8 | 120.1 |
O4—C9—C6 | 122.94 (17) | C3—C8—H8 | 120.1 |
O5—C9—C6 | 113.53 (15) | N2—C10—H10 | 124.8 |
N2—C10—N1 | 110.35 (16) | N1—C10—H10 | 124.8 |
N2—C11—C12 | 131.85 (16) | C13—C12—H12 | 122.0 |
N2—C11—C16 | 106.26 (15) | C11—C12—H12 | 122.0 |
C12—C11—C16 | 121.86 (17) | C12—C13—H13 | 119.0 |
C13—C12—C11 | 115.98 (18) | C14—C13—H13 | 119.0 |
C12—C13—C14 | 122.0 (2) | C15—C14—H14 | 119.1 |
C15—C14—C13 | 121.9 (2) | C13—C14—H14 | 119.1 |
C14—C15—C16 | 116.63 (18) | C14—C15—H15 | 121.7 |
N1—C16—C15 | 132.21 (16) | C16—C15—H15 | 121.7 |
N1—C16—C11 | 106.16 (15) | | |
| | | |
C3—O3—C2—C1 | 176.79 (13) | C5—C6—C9—O5 | −178.49 (15) |
O1—C1—C2—O3 | −163.18 (16) | C11—N2—C10—N1 | 0.7 (2) |
O2—C1—C2—O3 | 20.3 (2) | C16—N1—C10—N2 | −0.6 (2) |
C2—O3—C3—C4 | −174.90 (14) | C10—N2—C11—C12 | 177.3 (2) |
C2—O3—C3—C8 | 5.6 (2) | C10—N2—C11—C16 | −0.52 (19) |
O3—C3—C4—C5 | −178.04 (15) | N2—C11—C12—C13 | −177.71 (18) |
C8—C3—C4—C5 | 1.5 (2) | C16—C11—C12—C13 | −0.1 (3) |
C3—C4—C5—C6 | −0.7 (3) | C11—C12—C13—C14 | −0.4 (3) |
C4—C5—C6—C7 | −0.8 (2) | C12—C13—C14—C15 | 0.2 (3) |
C4—C5—C6—C9 | 179.67 (15) | C13—C14—C15—C16 | 0.5 (3) |
C5—C6—C7—C8 | 1.4 (3) | C10—N1—C16—C15 | −178.3 (2) |
C9—C6—C7—C8 | −179.06 (16) | C10—N1—C16—C11 | 0.2 (2) |
C6—C7—C8—C3 | −0.6 (3) | C14—C15—C16—N1 | 177.45 (19) |
O3—C3—C8—C7 | 178.60 (15) | C14—C15—C16—C11 | −1.0 (3) |
C4—C3—C8—C7 | −0.9 (3) | N2—C11—C16—N1 | 0.17 (19) |
C7—C6—C9—O4 | −178.07 (18) | C12—C11—C16—N1 | −177.96 (16) |
C5—C6—C9—O4 | 1.5 (3) | N2—C11—C16—C15 | 178.94 (16) |
C7—C6—C9—O5 | 2.0 (2) | C12—C11—C16—C15 | 0.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H19···O2i | 0.86 (2) | 1.76 (3) | 2.615 (3) | 173 (3) |
N1—H17···O1 | 0.90 (2) | 1.92 (3) | 2.718 (2) | 148 (2) |
N2—H18···O2ii | 0.90 (2) | 1.83 (3) | 2.691 (3) | 159 (2) |
Symmetry codes: (i) x, y, z+1; (ii) x, y−1, z. |