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organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023281/su6143sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023281/su6143Isup2.hkl |
CCDC reference: 253026
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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+2C9H7O5− | F(000) = 1064 |
Mr = 510.45 | Dx = 1.506 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 7992 reflections |
a = 11.255 (2) Å | θ = 3.2–27.4° |
b = 14.108 (3) Å | µ = 0.12 mm−1 |
c = 14.576 (3) Å | T = 295 K |
β = 103.37 (3)° | Prism, colorless |
V = 2251.9 (8) Å3 | 0.40 × 0.28 × 0.20 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2575 independent reflections |
Radiation source: fine-focus sealed tube | 2105 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
Tmin = 0.844, Tmax = 0.977 | k = −18→18 |
10631 measured reflections | l = −18→18 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H 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 parameters | Δρmax = 0.23 e Å−3 |
2 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.6565 (2) | 0.69554 (15) | 0.56875 (16) | 0.0574 (6) | |
O2 | 0.5886 (2) | 0.54831 (14) | 0.54130 (17) | 0.0603 (6) | |
H2o | 0.5000 | 0.5000 | 0.5000 | 0.078 (16)* | |
O3 | 0.44548 (19) | 0.77155 (13) | 0.48555 (15) | 0.0520 (6) | |
O4 | 0.3539 (2) | 1.10941 (14) | 0.44733 (18) | 0.0581 (6) | |
H4o | 0.354 (4) | 1.1694 (8) | 0.441 (3) | 0.074 (12)* | |
O5 | 0.1807 (2) | 1.12313 (16) | 0.3383 (2) | 0.0710 (8) | |
N1 | 0.9161 (2) | 0.68530 (17) | 0.69609 (18) | 0.0481 (6) | |
H1n | 0.851 (2) | 0.709 (3) | 0.662 (3) | 0.094 (15)* | |
C1 | 1.0000 | 0.7393 (3) | 0.7500 | 0.0520 (11) | |
H1 | 1.0000 | 0.8052 | 0.7500 | 0.062* | |
C2 | 0.9459 (2) | 0.59206 (18) | 0.71532 (19) | 0.0380 (6) | |
C3 | 0.8899 (3) | 0.5102 (2) | 0.6781 (2) | 0.0574 (8) | |
H3 | 0.8180 | 0.5104 | 0.6314 | 0.069* | |
C4 | 0.9468 (4) | 0.4273 (2) | 0.7143 (4) | 0.0813 (13) | |
H4 | 0.9132 | 0.3697 | 0.6903 | 0.098* | |
C5 | 0.5760 (3) | 0.63918 (19) | 0.5344 (2) | 0.0444 (6) | |
C6 | 0.4526 (3) | 0.67188 (19) | 0.4782 (2) | 0.0451 (7) | |
H6a | 0.4422 | 0.6538 | 0.4126 | 0.054* | |
H6b | 0.3883 | 0.6423 | 0.5024 | 0.054* | |
C7 | 0.3508 (2) | 0.81817 (19) | 0.4274 (2) | 0.0401 (6) | |
C8 | 0.3506 (2) | 0.91610 (19) | 0.4373 (2) | 0.0410 (6) | |
H8 | 0.4111 | 0.9457 | 0.4824 | 0.049* | |
C9 | 0.2600 (2) | 0.96936 (19) | 0.3796 (2) | 0.0416 (6) | |
C10 | 0.1703 (3) | 0.9258 (2) | 0.3120 (2) | 0.0528 (8) | |
H10 | 0.1099 | 0.9618 | 0.2728 | 0.063* | |
C11 | 0.1711 (3) | 0.8284 (2) | 0.3029 (3) | 0.0588 (8) | |
H11 | 0.1109 | 0.7990 | 0.2573 | 0.071* | |
C12 | 0.2597 (3) | 0.7742 (2) | 0.3606 (2) | 0.0515 (8) | |
H12 | 0.2584 | 0.7085 | 0.3548 | 0.062* | |
C13 | 0.2603 (3) | 1.0752 (2) | 0.3861 (2) | 0.0471 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0515 (13) | 0.0407 (11) | 0.0725 (15) | 0.0122 (10) | −0.0011 (10) | 0.0032 (10) |
O2 | 0.0605 (14) | 0.0303 (10) | 0.0833 (16) | 0.0150 (9) | 0.0025 (11) | 0.0083 (10) |
O3 | 0.0491 (12) | 0.0313 (10) | 0.0678 (14) | 0.0096 (8) | −0.0025 (10) | 0.0032 (9) |
O4 | 0.0481 (12) | 0.0311 (10) | 0.0840 (16) | 0.0091 (9) | −0.0075 (11) | 0.0008 (11) |
O5 | 0.0635 (15) | 0.0411 (12) | 0.0926 (18) | 0.0177 (11) | −0.0146 (13) | 0.0096 (12) |
N1 | 0.0485 (14) | 0.0379 (12) | 0.0577 (15) | 0.0128 (11) | 0.0117 (12) | 0.0087 (11) |
C1 | 0.071 (3) | 0.0184 (16) | 0.073 (3) | 0.000 | 0.031 (2) | 0.000 |
C2 | 0.0323 (12) | 0.0341 (13) | 0.0453 (14) | 0.0024 (10) | 0.0042 (10) | 0.0007 (11) |
C3 | 0.0409 (16) | 0.0513 (18) | 0.072 (2) | −0.0105 (13) | −0.0038 (14) | −0.0133 (15) |
C4 | 0.065 (2) | 0.0297 (15) | 0.139 (4) | −0.0106 (15) | 0.003 (2) | −0.0119 (19) |
C5 | 0.0482 (16) | 0.0298 (12) | 0.0550 (16) | 0.0092 (12) | 0.0118 (13) | 0.0041 (12) |
C6 | 0.0449 (15) | 0.0301 (13) | 0.0601 (17) | 0.0059 (11) | 0.0118 (13) | 0.0063 (12) |
C7 | 0.0336 (13) | 0.0350 (13) | 0.0512 (15) | 0.0040 (10) | 0.0086 (11) | 0.0053 (11) |
C8 | 0.0362 (13) | 0.0349 (13) | 0.0499 (15) | 0.0059 (10) | 0.0057 (11) | 0.0014 (11) |
C9 | 0.0335 (13) | 0.0362 (14) | 0.0536 (16) | 0.0079 (10) | 0.0071 (11) | 0.0062 (12) |
C10 | 0.0380 (15) | 0.0444 (16) | 0.069 (2) | 0.0043 (12) | −0.0011 (13) | 0.0129 (14) |
C11 | 0.0429 (17) | 0.0563 (19) | 0.068 (2) | −0.0089 (14) | −0.0060 (14) | 0.0026 (16) |
C12 | 0.0448 (16) | 0.0354 (14) | 0.071 (2) | −0.0040 (12) | 0.0055 (14) | 0.0005 (14) |
C13 | 0.0404 (15) | 0.0334 (14) | 0.0647 (18) | 0.0077 (11) | 0.0064 (13) | 0.0075 (13) |
Geometric parameters (Å, º) top
O1—C5 | 1.222 (4) | C9—C10 | 1.382 (4) |
O2—C5 | 1.291 (3) | C9—C13 | 1.496 (4) |
O3—C7 | 1.367 (3) | C10—C11 | 1.380 (5) |
O3—C6 | 1.414 (3) | C11—C12 | 1.378 (4) |
O4—C13 | 1.305 (4) | O2—H2o | 1.242 (2) |
O5—C13 | 1.207 (3) | O4—H4o | 0.85 (1) |
N1—C1 | 1.321 (3) | N1—H1n | 0.85 (1) |
N1—C2 | 1.370 (3) | C1—H1 | 0.9300 |
C1—N1i | 1.321 (3) | C3—H3 | 0.9300 |
C2—C3 | 1.367 (4) | C4—H4 | 0.9300 |
C2—C2i | 1.391 (5) | C6—H6a | 0.9700 |
C3—C4 | 1.378 (5) | C6—H6b | 0.9700 |
C4—C4i | 1.393 (8) | C8—H8 | 0.9300 |
C5—C6 | 1.512 (4) | C10—H10 | 0.9300 |
C7—C8 | 1.389 (4) | C11—H11 | 0.9300 |
C7—C12 | 1.386 (4) | C12—H12 | 0.9300 |
C8—C9 | 1.383 (4) | ||
C6—O3—C7 | 118.8 (2) | C5—O2—H2o | 116.5 (2) |
C1—N1—C2 | 108.9 (2) | C13—O4—H4o | 108 (3) |
N1—C2—C3 | 131.4 (3) | C1—N1—H1n | 121 (3) |
C3—C2—C2i | 122.3 (2) | C2—N1—H1n | 129 (3) |
N1—C2—C2i | 106.3 (2) | N1—C1—N1i | 109.6 (3) |
C2—C3—C4 | 115.7 (3) | N1—C1—H1 | 125.2 |
C3—C4—C4i | 121.9 (2) | N1i—C1—H1 | 125.2 |
O1—C5—O2 | 123.8 (3) | C2—C3—H3 | 122.1 |
O1—C5—C6 | 121.6 (2) | C4—C3—H3 | 122.1 |
O2—C5—C6 | 114.6 (3) | C3—C4—H4 | 119.0 |
O3—C6—C5 | 108.9 (2) | C4i—C4—H4 | 119.0 |
O3—C7—C8 | 115.7 (2) | O3—C6—H6a | 109.9 |
O3—C7—C12 | 124.3 (2) | C5—C6—H6a | 109.9 |
C8—C7—C12 | 119.9 (3) | O3—C6—H6b | 109.9 |
C7—C8—C9 | 119.7 (3) | C5—C6—H6b | 109.9 |
C8—C9—C10 | 120.4 (3) | H6a—C6—H6b | 108.3 |
C10—C9—C13 | 118.7 (2) | C9—C8—H8 | 120.1 |
C8—C9—C13 | 120.9 (3) | C7—C8—H8 | 120.1 |
C9—C10—C11 | 119.4 (3) | C11—C10—H10 | 120.3 |
C7—C12—C11 | 119.6 (3) | C9—C10—H10 | 120.3 |
C10—C11—C12 | 120.9 (3) | C12—C11—H11 | 119.5 |
O5—C13—O4 | 124.2 (3) | C10—C11—H11 | 119.5 |
O4—C13—C9 | 113.7 (2) | C11—C12—H12 | 120.2 |
O5—C13—C9 | 122.1 (3) | C7—C12—H12 | 120.2 |
C2—N1—C1—N1i | 0.04 (14) | C12—C7—C8—C9 | −0.6 (4) |
C1—N1—C2—C3 | −179.2 (3) | C7—C8—C9—C10 | −0.4 (4) |
C1—N1—C2—C2i | −0.1 (4) | C7—C8—C9—C13 | −177.6 (3) |
N1—C2—C3—C4 | 179.5 (4) | C8—C9—C10—C11 | 0.6 (5) |
C2i—C2—C3—C4 | 0.5 (5) | C13—C9—C10—C11 | 177.9 (3) |
C2—C3—C4—C4i | 1.4 (8) | C9—C10—C11—C12 | 0.2 (5) |
H2O—O2—C5—O1 | −177.7 (3) | C10—C11—C12—C7 | −1.3 (5) |
H2O—O2—C5—C6 | 1.3 (4) | O3—C7—C12—C11 | −177.4 (3) |
C7—O3—C6—C5 | 168.8 (2) | C8—C7—C12—C11 | 1.5 (5) |
O1—C5—C6—O3 | −8.0 (4) | C10—C9—C13—O5 | 4.7 (5) |
O2—C5—C6—O3 | 173.0 (3) | C8—C9—C13—O5 | −178.1 (3) |
C6—O3—C7—C12 | 0.0 (4) | C10—C9—C13—O4 | −175.1 (3) |
C6—O3—C7—C8 | −178.9 (3) | C8—C9—C13—O4 | 2.1 (4) |
O3—C7—C8—C9 | 178.3 (2) |
Symmetry code: (i) −x+2, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4o···O1ii | 0.85 (1) | 1.91 (1) | 2.762 (3) | 176 (4) |
N1—H1n···O1 | 0.85 (1) | 2.30 (2) | 3.082 (3) | 152 (4) |
N1—H1n···O5ii | 0.85 (1) | 2.39 (4) | 2.914 (2) | 120 (4) |
O2—H2o···O2iii | 1.24 (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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