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The anion in the structure of the title compound, C7H7N2+·H+·2C9H7O5-, has a CO2H unit on the aromatic ring. Two anions are linked through an `acid H' atom (which lies on a center of inversion) to give a monoanionic entity. Adjacent entities are linked into a linear chain through hydrogen bonding involving the CO2H units. The chains are connected into a layer structure through the benzimidazolium cations, which possess C2 symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023281/su6143sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023281/su6143Isup2.hkl
Contains datablock I

CCDC reference: 253026

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.069
  • wR factor = 0.196
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT355_ALERT_3_A Long O-H Bond (0.82A) O2 - H2O ... 1.24 Ang.
Author Response: The significance of the "acid hydrogen" is discussed in the text.

Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O2 - H2O ... ? PLAT432_ALERT_2_B Short Inter X...Y Contact O5 .. C1 .. 2.89 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.844 0.977 Tmin' and Tmax expected: 0.953 0.977 RR' = 0.885 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.41 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat N1 -H1N 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat N1 -H1N 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat N1 -H1N 1.555 1.555 PLAT751_ALERT_4_C Bond Calc 1.24245, Rep 1.242(2) ...... Senseless su O2 -H2O 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 116.46, Rep 116.5(2) ...... Senseless su C5 -O2 -H2O 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc -177.67, Rep -177.7(3) ...... Senseless su H2O -O2 -C5 -O1 1.555 1.555 1.555 1.555 PLAT753_ALERT_4_C Torsion Calc 1.34, Rep 1.3(4) ...... Senseless su H2O -O2 -C5 -C6 1.555 1.555 1.555 1.555 PLAT755_ALERT_4_C D-H Calc 1.24245, Rep 1.242(2) ...... Senseless su O2 -H2O 1.555 1.555 PLAT756_ALERT_4_C H...A Calc 1.24245, Rep 1.242(2) ...... Senseless su H2O -O2 1.555 5.666
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C25 H22 N2 O10 Atom count from _chemical_formula_moiety:C16 H16 N2 O5
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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 hydrogen bis(3-carboxyphenoxyacetate) top
Crystal data top
C7H7N2+·H+2C9H7O5F(000) = 1064
Mr = 510.45Dx = 1.506 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7992 reflections
a = 11.255 (2) Åθ = 3.2–27.4°
b = 14.108 (3) ŵ = 0.12 mm1
c = 14.576 (3) ÅT = 295 K
β = 103.37 (3)°Prism, colorless
V = 2251.9 (8) Å30.40 × 0.28 × 0.20 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2575 independent reflections
Radiation source: fine-focus sealed tube2105 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1414
Tmin = 0.844, Tmax = 0.977k = 1818
10631 measured reflectionsl = 1818
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H atoms treated by a mixture of independent and constrained refinement
S = 1.18 w = 1/[σ2(Fo2) + (0.0715P)2 + 3.922P]
where P = (Fo2 + 2Fc2)/3
2575 reflections(Δ/σ)max = 0.001
177 parametersΔρmax = 0.23 e Å3
2 restraintsΔρmin = 0.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6565 (2)0.69554 (15)0.56875 (16)0.0574 (6)
O20.5886 (2)0.54831 (14)0.54130 (17)0.0603 (6)
H2o0.50000.50000.50000.078 (16)*
O30.44548 (19)0.77155 (13)0.48555 (15)0.0520 (6)
O40.3539 (2)1.10941 (14)0.44733 (18)0.0581 (6)
H4o0.354 (4)1.1694 (8)0.441 (3)0.074 (12)*
O50.1807 (2)1.12313 (16)0.3383 (2)0.0710 (8)
N10.9161 (2)0.68530 (17)0.69609 (18)0.0481 (6)
H1n0.851 (2)0.709 (3)0.662 (3)0.094 (15)*
C11.00000.7393 (3)0.75000.0520 (11)
H11.00000.80520.75000.062*
C20.9459 (2)0.59206 (18)0.71532 (19)0.0380 (6)
C30.8899 (3)0.5102 (2)0.6781 (2)0.0574 (8)
H30.81800.51040.63140.069*
C40.9468 (4)0.4273 (2)0.7143 (4)0.0813 (13)
H40.91320.36970.69030.098*
C50.5760 (3)0.63918 (19)0.5344 (2)0.0444 (6)
C60.4526 (3)0.67188 (19)0.4782 (2)0.0451 (7)
H6a0.44220.65380.41260.054*
H6b0.38830.64230.50240.054*
C70.3508 (2)0.81817 (19)0.4274 (2)0.0401 (6)
C80.3506 (2)0.91610 (19)0.4373 (2)0.0410 (6)
H80.41110.94570.48240.049*
C90.2600 (2)0.96936 (19)0.3796 (2)0.0416 (6)
C100.1703 (3)0.9258 (2)0.3120 (2)0.0528 (8)
H100.10990.96180.27280.063*
C110.1711 (3)0.8284 (2)0.3029 (3)0.0588 (8)
H110.11090.79900.25730.071*
C120.2597 (3)0.7742 (2)0.3606 (2)0.0515 (8)
H120.25840.70850.35480.062*
C130.2603 (3)1.0752 (2)0.3861 (2)0.0471 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0515 (13)0.0407 (11)0.0725 (15)0.0122 (10)0.0011 (10)0.0032 (10)
O20.0605 (14)0.0303 (10)0.0833 (16)0.0150 (9)0.0025 (11)0.0083 (10)
O30.0491 (12)0.0313 (10)0.0678 (14)0.0096 (8)0.0025 (10)0.0032 (9)
O40.0481 (12)0.0311 (10)0.0840 (16)0.0091 (9)0.0075 (11)0.0008 (11)
O50.0635 (15)0.0411 (12)0.0926 (18)0.0177 (11)0.0146 (13)0.0096 (12)
N10.0485 (14)0.0379 (12)0.0577 (15)0.0128 (11)0.0117 (12)0.0087 (11)
C10.071 (3)0.0184 (16)0.073 (3)0.0000.031 (2)0.000
C20.0323 (12)0.0341 (13)0.0453 (14)0.0024 (10)0.0042 (10)0.0007 (11)
C30.0409 (16)0.0513 (18)0.072 (2)0.0105 (13)0.0038 (14)0.0133 (15)
C40.065 (2)0.0297 (15)0.139 (4)0.0106 (15)0.003 (2)0.0119 (19)
C50.0482 (16)0.0298 (12)0.0550 (16)0.0092 (12)0.0118 (13)0.0041 (12)
C60.0449 (15)0.0301 (13)0.0601 (17)0.0059 (11)0.0118 (13)0.0063 (12)
C70.0336 (13)0.0350 (13)0.0512 (15)0.0040 (10)0.0086 (11)0.0053 (11)
C80.0362 (13)0.0349 (13)0.0499 (15)0.0059 (10)0.0057 (11)0.0014 (11)
C90.0335 (13)0.0362 (14)0.0536 (16)0.0079 (10)0.0071 (11)0.0062 (12)
C100.0380 (15)0.0444 (16)0.069 (2)0.0043 (12)0.0011 (13)0.0129 (14)
C110.0429 (17)0.0563 (19)0.068 (2)0.0089 (14)0.0060 (14)0.0026 (16)
C120.0448 (16)0.0354 (14)0.071 (2)0.0040 (12)0.0055 (14)0.0005 (14)
C130.0404 (15)0.0334 (14)0.0647 (18)0.0077 (11)0.0064 (13)0.0075 (13)
Geometric parameters (Å, º) top
O1—C51.222 (4)C9—C101.382 (4)
O2—C51.291 (3)C9—C131.496 (4)
O3—C71.367 (3)C10—C111.380 (5)
O3—C61.414 (3)C11—C121.378 (4)
O4—C131.305 (4)O2—H2o1.242 (2)
O5—C131.207 (3)O4—H4o0.85 (1)
N1—C11.321 (3)N1—H1n0.85 (1)
N1—C21.370 (3)C1—H10.9300
C1—N1i1.321 (3)C3—H30.9300
C2—C31.367 (4)C4—H40.9300
C2—C2i1.391 (5)C6—H6a0.9700
C3—C41.378 (5)C6—H6b0.9700
C4—C4i1.393 (8)C8—H80.9300
C5—C61.512 (4)C10—H100.9300
C7—C81.389 (4)C11—H110.9300
C7—C121.386 (4)C12—H120.9300
C8—C91.383 (4)
C6—O3—C7118.8 (2)C5—O2—H2o116.5 (2)
C1—N1—C2108.9 (2)C13—O4—H4o108 (3)
N1—C2—C3131.4 (3)C1—N1—H1n121 (3)
C3—C2—C2i122.3 (2)C2—N1—H1n129 (3)
N1—C2—C2i106.3 (2)N1—C1—N1i109.6 (3)
C2—C3—C4115.7 (3)N1—C1—H1125.2
C3—C4—C4i121.9 (2)N1i—C1—H1125.2
O1—C5—O2123.8 (3)C2—C3—H3122.1
O1—C5—C6121.6 (2)C4—C3—H3122.1
O2—C5—C6114.6 (3)C3—C4—H4119.0
O3—C6—C5108.9 (2)C4i—C4—H4119.0
O3—C7—C8115.7 (2)O3—C6—H6a109.9
O3—C7—C12124.3 (2)C5—C6—H6a109.9
C8—C7—C12119.9 (3)O3—C6—H6b109.9
C7—C8—C9119.7 (3)C5—C6—H6b109.9
C8—C9—C10120.4 (3)H6a—C6—H6b108.3
C10—C9—C13118.7 (2)C9—C8—H8120.1
C8—C9—C13120.9 (3)C7—C8—H8120.1
C9—C10—C11119.4 (3)C11—C10—H10120.3
C7—C12—C11119.6 (3)C9—C10—H10120.3
C10—C11—C12120.9 (3)C12—C11—H11119.5
O5—C13—O4124.2 (3)C10—C11—H11119.5
O4—C13—C9113.7 (2)C11—C12—H12120.2
O5—C13—C9122.1 (3)C7—C12—H12120.2
C2—N1—C1—N1i0.04 (14)C12—C7—C8—C90.6 (4)
C1—N1—C2—C3179.2 (3)C7—C8—C9—C100.4 (4)
C1—N1—C2—C2i0.1 (4)C7—C8—C9—C13177.6 (3)
N1—C2—C3—C4179.5 (4)C8—C9—C10—C110.6 (5)
C2i—C2—C3—C40.5 (5)C13—C9—C10—C11177.9 (3)
C2—C3—C4—C4i1.4 (8)C9—C10—C11—C120.2 (5)
H2O—O2—C5—O1177.7 (3)C10—C11—C12—C71.3 (5)
H2O—O2—C5—C61.3 (4)O3—C7—C12—C11177.4 (3)
C7—O3—C6—C5168.8 (2)C8—C7—C12—C111.5 (5)
O1—C5—C6—O38.0 (4)C10—C9—C13—O54.7 (5)
O2—C5—C6—O3173.0 (3)C8—C9—C13—O5178.1 (3)
C6—O3—C7—C120.0 (4)C10—C9—C13—O4175.1 (3)
C6—O3—C7—C8178.9 (3)C8—C9—C13—O42.1 (4)
O3—C7—C8—C9178.3 (2)
Symmetry code: (i) x+2, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4o···O1ii0.85 (1)1.91 (1)2.762 (3)176 (4)
N1—H1n···O10.85 (1)2.30 (2)3.082 (3)152 (4)
N1—H1n···O5ii0.85 (1)2.39 (4)2.914 (2)120 (4)
O2—H2o···O2iii1.24 (1)1.24 (1)2.484 (2)180
Symmetry codes: (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1.
 

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