In the title compound, C7H7N2+·C8H4NO6−, the partially overlapped arrangement and the shorter face-to-face distance of 3.457 (4) Å indicate π–π stacking between parallel benzimidazolium cations, whereas the longer face-to-face distance of 3.649 (6) Å suggests normal van der Waals contacts between parallel benzene rings of neighbouring nitroterephthalate anions.
Supporting information
CCDC reference: 293813
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.048
- wR factor = 0.146
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT213_ALERT_2_C Atom O1 has ADP max/min Ratio ............. 3.10 prolat
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.38
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
4 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Benzimidazolium hydrogen nitroterephthalate
top
Crystal data top
C7H7N2+·C8H4NO6− | Z = 2 |
Mr = 329.27 | F(000) = 340 |
Triclinic, P1 | Dx = 1.493 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.445 (6) Å | Cell parameters from 6302 reflections |
b = 9.076 (4) Å | θ = 2.8–25.0° |
c = 9.755 (4) Å | µ = 0.12 mm−1 |
α = 98.051 (2)° | T = 295 K |
β = 91.905 (2)° | Block, colorless |
γ = 97.891 (2)° | 0.36 × 0.30 × 0.24 mm |
V = 732.3 (7) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2593 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
Detector resolution: 10.00 pixels mm-1 | h = −10→10 |
ω scans | k = −11→11 |
7282 measured reflections | l = −12→12 |
3323 independent 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) = 0.146 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0827P)2 + 0.1449P] where P = (Fo2 + 2Fc2)/3 |
3323 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.29 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 | |
N1 | 0.26149 (19) | −0.01741 (16) | 0.51277 (15) | 0.0427 (4) | |
H1 | 0.2876 | −0.1115 | 0.4880 | 0.064* | |
N2 | 0.17873 (18) | 0.38693 (15) | 0.13198 (14) | 0.0389 (3) | |
N3 | 0.2483 (2) | 0.21803 (17) | 0.50719 (16) | 0.0474 (4) | |
H3 | 0.2646 | 0.3015 | 0.4778 | 0.071* | |
O1 | 0.3040 (3) | 0.46138 (16) | 0.39020 (14) | 0.0837 (6) | |
O2 | 0.34926 (18) | 0.70257 (14) | 0.47214 (11) | 0.0461 (3) | |
O3 | 0.45482 (19) | 0.85105 (14) | −0.20937 (12) | 0.0515 (4) | |
O4 | 0.33632 (18) | 0.61705 (14) | −0.28250 (11) | 0.0514 (4) | |
H4A | 0.3500 | 0.6518 | −0.3715 | 0.077* | |
O5 | 0.0462 (2) | 0.39581 (18) | 0.1715 (2) | 0.0803 (6) | |
O6 | 0.2278 (2) | 0.27049 (15) | 0.0980 (2) | 0.0764 (5) | |
C2 | 0.3078 (2) | 0.0994 (2) | 0.44974 (19) | 0.0479 (4) | |
H2 | 0.3734 | 0.0980 | 0.3750 | 0.058* | |
C4 | 0.0672 (2) | 0.2606 (2) | 0.7067 (2) | 0.0495 (5) | |
H4 | 0.0608 | 0.3615 | 0.7036 | 0.059* | |
C5 | −0.0105 (3) | 0.1844 (3) | 0.8021 (2) | 0.0566 (5) | |
H5 | −0.0698 | 0.2354 | 0.8667 | 0.068* | |
C6 | −0.0033 (3) | 0.0321 (3) | 0.8051 (2) | 0.0559 (5) | |
H6 | −0.0594 | −0.0157 | 0.8708 | 0.067* | |
C7 | 0.0839 (2) | −0.0495 (2) | 0.71424 (19) | 0.0464 (4) | |
H7 | 0.0884 | −0.1508 | 0.7169 | 0.056* | |
C8 | 0.1651 (2) | 0.02747 (18) | 0.61788 (17) | 0.0367 (4) | |
C9 | 0.1565 (2) | 0.17870 (18) | 0.61449 (17) | 0.0386 (4) | |
C11 | 0.3314 (2) | 0.59369 (18) | 0.37617 (15) | 0.0356 (4) | |
C12 | 0.34878 (19) | 0.62790 (16) | 0.22947 (14) | 0.0296 (3) | |
C13 | 0.4375 (2) | 0.76037 (17) | 0.20298 (15) | 0.0348 (4) | |
H13 | 0.4864 | 0.8295 | 0.2768 | 0.042* | |
C14 | 0.4548 (2) | 0.79168 (18) | 0.06902 (15) | 0.0360 (4) | |
H14 | 0.5146 | 0.8813 | 0.0536 | 0.043* | |
C15 | 0.38303 (19) | 0.68951 (17) | −0.04251 (14) | 0.0311 (3) | |
C16 | 0.29692 (19) | 0.55516 (17) | −0.01966 (14) | 0.0325 (3) | |
H16 | 0.2509 | 0.4847 | −0.0936 | 0.039* | |
C17 | 0.28060 (19) | 0.52764 (16) | 0.11549 (15) | 0.0301 (3) | |
C18 | 0.3970 (2) | 0.72854 (18) | −0.18666 (15) | 0.0361 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0542 (9) | 0.0338 (7) | 0.0405 (8) | 0.0041 (6) | 0.0057 (6) | 0.0085 (6) |
N2 | 0.0504 (9) | 0.0319 (7) | 0.0335 (7) | −0.0010 (6) | 0.0069 (6) | 0.0071 (5) |
N3 | 0.0603 (10) | 0.0337 (7) | 0.0489 (9) | −0.0028 (7) | 0.0002 (7) | 0.0186 (6) |
O1 | 0.178 (2) | 0.0372 (8) | 0.0332 (7) | −0.0085 (9) | 0.0056 (9) | 0.0177 (6) |
O2 | 0.0809 (9) | 0.0393 (6) | 0.0191 (5) | 0.0095 (6) | 0.0048 (5) | 0.0061 (5) |
O3 | 0.0843 (10) | 0.0408 (7) | 0.0289 (6) | −0.0032 (6) | 0.0081 (6) | 0.0144 (5) |
O4 | 0.0858 (10) | 0.0454 (7) | 0.0193 (5) | −0.0057 (6) | 0.0033 (5) | 0.0070 (5) |
O5 | 0.0592 (10) | 0.0558 (9) | 0.1295 (16) | −0.0001 (7) | 0.0396 (10) | 0.0260 (10) |
O6 | 0.0948 (13) | 0.0289 (7) | 0.1056 (13) | 0.0037 (7) | 0.0415 (10) | 0.0067 (7) |
C2 | 0.0549 (11) | 0.0486 (10) | 0.0407 (9) | 0.0004 (8) | 0.0060 (8) | 0.0143 (8) |
C4 | 0.0528 (11) | 0.0384 (9) | 0.0551 (11) | 0.0094 (8) | −0.0077 (8) | −0.0010 (8) |
C5 | 0.0518 (12) | 0.0666 (13) | 0.0491 (11) | 0.0108 (10) | 0.0035 (9) | −0.0024 (9) |
C6 | 0.0537 (12) | 0.0675 (13) | 0.0473 (11) | 0.0008 (10) | 0.0092 (9) | 0.0175 (9) |
C7 | 0.0533 (11) | 0.0390 (9) | 0.0473 (10) | −0.0029 (8) | 0.0018 (8) | 0.0168 (8) |
C8 | 0.0418 (9) | 0.0310 (8) | 0.0364 (8) | 0.0005 (6) | −0.0023 (6) | 0.0078 (6) |
C9 | 0.0439 (9) | 0.0307 (8) | 0.0399 (9) | −0.0021 (6) | −0.0054 (7) | 0.0089 (6) |
C11 | 0.0527 (10) | 0.0329 (8) | 0.0226 (7) | 0.0048 (7) | 0.0045 (6) | 0.0100 (6) |
C12 | 0.0409 (8) | 0.0294 (7) | 0.0196 (6) | 0.0058 (6) | 0.0029 (5) | 0.0062 (5) |
C13 | 0.0474 (9) | 0.0320 (8) | 0.0226 (7) | −0.0023 (6) | −0.0007 (6) | 0.0041 (6) |
C14 | 0.0493 (9) | 0.0315 (8) | 0.0263 (7) | −0.0031 (6) | 0.0043 (6) | 0.0093 (6) |
C15 | 0.0416 (8) | 0.0329 (8) | 0.0202 (7) | 0.0051 (6) | 0.0042 (5) | 0.0085 (6) |
C16 | 0.0434 (9) | 0.0321 (8) | 0.0210 (7) | 0.0030 (6) | 0.0016 (6) | 0.0031 (6) |
C17 | 0.0387 (8) | 0.0265 (7) | 0.0256 (7) | 0.0022 (6) | 0.0049 (6) | 0.0072 (5) |
C18 | 0.0500 (10) | 0.0379 (8) | 0.0220 (7) | 0.0060 (7) | 0.0056 (6) | 0.0093 (6) |
Geometric parameters (Å, º) top
N1—C2 | 1.319 (2) | C5—C6 | 1.397 (3) |
N1—C8 | 1.382 (2) | C5—H5 | 0.9300 |
N1—H1 | 0.9129 | C6—C7 | 1.372 (3) |
N2—O6 | 1.196 (2) | C6—H6 | 0.9300 |
N2—O5 | 1.205 (2) | C7—C8 | 1.392 (2) |
N2—C17 | 1.470 (2) | C7—H7 | 0.9300 |
N3—C2 | 1.313 (3) | C8—C9 | 1.389 (2) |
N3—C9 | 1.381 (2) | C11—C12 | 1.5138 (19) |
N3—H3 | 0.8423 | C12—C17 | 1.388 (2) |
O1—C11 | 1.219 (2) | C12—C13 | 1.388 (2) |
O2—C11 | 1.252 (2) | C13—C14 | 1.384 (2) |
O3—C18 | 1.204 (2) | C13—H13 | 0.9300 |
O4—C18 | 1.312 (2) | C14—C15 | 1.389 (2) |
O4—H4A | 0.9701 | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.382 (2) |
C4—C5 | 1.367 (3) | C15—C18 | 1.502 (2) |
C4—C9 | 1.393 (3) | C16—C17 | 1.384 (2) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
| | | |
C2—N1—C8 | 108.14 (15) | N3—C9—C8 | 105.92 (15) |
C2—N1—H1 | 124.8 | N3—C9—C4 | 132.06 (17) |
C8—N1—H1 | 127.0 | C8—C9—C4 | 122.01 (17) |
O6—N2—O5 | 123.77 (16) | O1—C11—O2 | 125.78 (14) |
O6—N2—C17 | 118.54 (15) | O1—C11—C12 | 116.63 (14) |
O5—N2—C17 | 117.54 (14) | O2—C11—C12 | 117.58 (14) |
C2—N3—C9 | 108.79 (15) | C17—C12—C13 | 116.94 (13) |
C2—N3—H3 | 122.5 | C17—C12—C11 | 121.93 (14) |
C9—N3—H3 | 128.7 | C13—C12—C11 | 121.12 (13) |
C18—O4—H4A | 107.3 | C14—C13—C12 | 121.36 (14) |
N3—C2—N1 | 110.55 (17) | C14—C13—H13 | 119.3 |
N3—C2—H2 | 124.7 | C12—C13—H13 | 119.3 |
N1—C2—H2 | 124.7 | C13—C14—C15 | 120.10 (14) |
C5—C4—C9 | 116.40 (18) | C13—C14—H14 | 119.9 |
C5—C4—H4 | 121.8 | C15—C14—H14 | 119.9 |
C9—C4—H4 | 121.8 | C16—C15—C14 | 119.89 (13) |
C4—C5—C6 | 121.77 (19) | C16—C15—C18 | 120.79 (13) |
C4—C5—H5 | 119.1 | C14—C15—C18 | 119.31 (14) |
C6—C5—H5 | 119.1 | C15—C16—C17 | 118.65 (13) |
C7—C6—C5 | 122.19 (18) | C15—C16—H16 | 120.7 |
C7—C6—H6 | 118.9 | C17—C16—H16 | 120.7 |
C5—C6—H6 | 118.9 | C16—C17—C12 | 123.04 (14) |
C6—C7—C8 | 116.51 (18) | C16—C17—N2 | 115.50 (13) |
C6—C7—H7 | 121.7 | C12—C17—N2 | 121.40 (13) |
C8—C7—H7 | 121.7 | O3—C18—O4 | 124.56 (14) |
N1—C8—C9 | 106.60 (15) | O3—C18—C15 | 122.61 (14) |
N1—C8—C7 | 132.28 (16) | O4—C18—C15 | 112.80 (14) |
C9—C8—C7 | 121.12 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.91 | 1.82 | 2.724 (3) | 170 |
N3—H3···O1 | 0.84 | 1.78 | 2.619 (3) | 171 |
O4—H4A···O2ii | 0.97 | 1.65 | 2.619 (2) | 173 |
Symmetry codes: (i) x, y−1, z; (ii) x, y, z−1. |