In the title compound, C18H16N3O2+·ClO4-, the almost planar cation contains bicyclic chromenone and benzimidazole moieties, which are rotated slightly relative to each other. The positive charge of the cation is located on the pyrilium ring and causes noticeable aromatization of the O-C and C-C bonds. One of the H atoms of the amino group is involved in an intramolecular hydrogen bond which closes the six-membered pseudo-ring in the cation. The second H atom of the amino group participates in a hydrogen bond with one of the O atoms of the perchlorate anion.
Supporting information
CCDC reference: 203003
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.099
- Data-to-parameter ratio = 12.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK and XPREP (Siemens, 1991); program(s) used to solve structure: SHELXS (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999).
2-Amino-7-methoxy-3-(1-methyl-1
H-benzimidazol-2-yl)chromenium perchlorate
top
Crystal data top
C18H16N3O2+·ClO4− | F(000) = 840 |
Mr = 405.79 | Dx = 1.520 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6272 (17) Å | Cell parameters from 24 reflections |
b = 10.979 (3) Å | θ = 11.0–12.0° |
c = 18.788 (7) Å | µ = 0.26 mm−1 |
β = 94.71 (3)° | T = 293 K |
V = 1773.5 (9) Å3 | Complex polyhedron, red |
Z = 4 | 0.4 × 0.3 × 0.2 mm |
Data collection top
Siemens P3/PC diffractometer | Rint = 0.043 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 2.5° |
Graphite monochromator | h = 0→10 |
2θ/θ scans | k = 0→13 |
3526 measured reflections | l = −22→22 |
3297 independent reflections | 2 standard reflections every 98 reflections |
1992 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3297 reflections | Δρmax = 0.23 e Å−3 |
256 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.0017xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0017 (5) |
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 | 0.2177 (2) | 0.09447 (18) | 0.53233 (9) | 0.0370 (5) | |
O2 | 0.4061 (3) | −0.2083 (2) | 0.38248 (11) | 0.0481 (6) | |
N1 | 0.1405 (3) | 0.2207 (2) | 0.61471 (12) | 0.0435 (7) | |
H1A | 0.2088 | 0.1854 | 0.6436 | 0.052* | |
H1B | 0.0845 | 0.2786 | 0.6297 | 0.052* | |
N2 | −0.1836 (3) | 0.4127 (2) | 0.46649 (12) | 0.0338 (6) | |
N3 | −0.0873 (3) | 0.3797 (2) | 0.58101 (12) | 0.0373 (6) | |
C2 | 0.1217 (3) | 0.1862 (3) | 0.54781 (15) | 0.0334 (7) | |
C3 | 0.0097 (3) | 0.2379 (3) | 0.49303 (14) | 0.0296 (6) | |
C4 | 0.0008 (3) | 0.1797 (3) | 0.42742 (15) | 0.0354 (7) | |
H4 | −0.0728 | 0.2066 | 0.3920 | 0.042* | |
C5 | 0.0930 (3) | 0.0197 (3) | 0.34432 (15) | 0.0402 (7) | |
H5 | 0.0212 | 0.0445 | 0.3075 | 0.048* | |
C6 | 0.1930 (3) | −0.0758 (3) | 0.33348 (15) | 0.0408 (7) | |
H6 | 0.1873 | −0.1150 | 0.2895 | 0.049* | |
C7 | 0.3041 (3) | −0.1147 (3) | 0.38878 (16) | 0.0365 (7) | |
C8 | 0.3112 (3) | −0.0554 (3) | 0.45627 (15) | 0.0373 (7) | |
H8 | 0.3827 | −0.0796 | 0.4933 | 0.045* | |
C9 | 0.0993 (3) | 0.0806 (3) | 0.41163 (14) | 0.0314 (6) | |
C10 | 0.2093 (3) | 0.0390 (3) | 0.46522 (14) | 0.0323 (7) | |
C11 | −0.0868 (3) | 0.3423 (3) | 0.51298 (15) | 0.0320 (6) | |
C12 | −0.2499 (3) | 0.5016 (3) | 0.50854 (15) | 0.0316 (6) | |
C13 | −0.3558 (3) | 0.5969 (3) | 0.49194 (17) | 0.0412 (7) | |
H13 | −0.3968 | 0.6109 | 0.4453 | 0.049* | |
C14 | −0.3963 (4) | 0.6687 (3) | 0.54801 (17) | 0.0448 (8) | |
H14 | −0.4661 | 0.7324 | 0.5386 | 0.054* | |
C15 | −0.3347 (4) | 0.6483 (3) | 0.61938 (18) | 0.0482 (9) | |
H15 | −0.3650 | 0.6986 | 0.6555 | 0.058* | |
C16 | −0.2299 (4) | 0.5545 (3) | 0.63627 (17) | 0.0469 (8) | |
H16 | −0.1880 | 0.5419 | 0.6829 | 0.056* | |
C17 | −0.1893 (3) | 0.4788 (3) | 0.57931 (15) | 0.0344 (7) | |
C18 | −0.2094 (4) | 0.4112 (3) | 0.38722 (15) | 0.0446 (8) | |
H18A | −0.1111 | 0.4051 | 0.3670 | 0.067* | |
H18B | −0.2606 | 0.4850 | 0.3711 | 0.067* | |
H18C | −0.2730 | 0.3426 | 0.3724 | 0.067* | |
C19 | 0.4059 (4) | −0.2701 (3) | 0.31384 (16) | 0.0519 (9) | |
H19A | 0.3054 | −0.3054 | 0.3017 | 0.078* | |
H19B | 0.4833 | −0.3331 | 0.3169 | 0.078* | |
H19C | 0.4288 | −0.2125 | 0.2777 | 0.078* | |
Cl | 0.36755 (9) | −0.08682 (7) | 0.70706 (4) | 0.0405 (2) | |
O3 | 0.3694 (3) | −0.1181 (2) | 0.63269 (11) | 0.0646 (7) | |
O4 | 0.5102 (3) | −0.1211 (3) | 0.74588 (14) | 0.0854 (10) | |
O5 | 0.3416 (4) | 0.0426 (2) | 0.71428 (14) | 0.0817 (9) | |
O6 | 0.2427 (3) | −0.1529 (3) | 0.73705 (14) | 0.0749 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0438 (12) | 0.0351 (11) | 0.0308 (10) | 0.0063 (10) | −0.0043 (9) | −0.0023 (9) |
O2 | 0.0522 (15) | 0.0495 (14) | 0.0424 (13) | 0.0171 (11) | 0.0032 (11) | −0.0046 (11) |
N1 | 0.0512 (17) | 0.0482 (17) | 0.0299 (14) | 0.0090 (14) | −0.0034 (12) | −0.0010 (12) |
N2 | 0.0320 (13) | 0.0369 (14) | 0.0325 (13) | −0.0012 (12) | 0.0022 (10) | 0.0018 (12) |
N3 | 0.0400 (15) | 0.0419 (15) | 0.0303 (13) | 0.0055 (12) | 0.0045 (11) | −0.0015 (11) |
C2 | 0.0353 (17) | 0.0302 (16) | 0.0352 (16) | −0.0068 (13) | 0.0067 (13) | 0.0011 (13) |
C3 | 0.0301 (15) | 0.0306 (15) | 0.0282 (14) | −0.0034 (13) | 0.0032 (12) | 0.0041 (12) |
C4 | 0.0328 (16) | 0.0379 (17) | 0.0343 (16) | 0.0009 (14) | −0.0042 (13) | −0.0007 (13) |
C5 | 0.0367 (18) | 0.0435 (18) | 0.0396 (17) | 0.0054 (15) | −0.0026 (14) | −0.0007 (15) |
C6 | 0.0419 (18) | 0.0460 (18) | 0.0342 (16) | −0.0009 (16) | 0.0019 (13) | 0.0005 (15) |
C7 | 0.0361 (17) | 0.0349 (18) | 0.0394 (17) | 0.0025 (13) | 0.0081 (13) | 0.0020 (13) |
C8 | 0.0387 (18) | 0.0338 (17) | 0.0384 (17) | 0.0005 (13) | −0.0034 (13) | 0.0040 (13) |
C9 | 0.0301 (15) | 0.0314 (15) | 0.0326 (15) | −0.0003 (13) | 0.0014 (12) | −0.0019 (13) |
C10 | 0.0348 (16) | 0.0327 (16) | 0.0293 (15) | −0.0010 (13) | 0.0015 (12) | −0.0001 (12) |
C11 | 0.0309 (16) | 0.0287 (15) | 0.0362 (16) | −0.0035 (12) | 0.0025 (13) | 0.0003 (13) |
C12 | 0.0252 (15) | 0.0299 (15) | 0.0396 (16) | −0.0041 (12) | 0.0022 (12) | 0.0031 (13) |
C13 | 0.0346 (17) | 0.0391 (18) | 0.0496 (19) | 0.0001 (15) | 0.0019 (14) | 0.0038 (16) |
C14 | 0.0392 (19) | 0.0349 (17) | 0.061 (2) | 0.0076 (15) | 0.0099 (16) | 0.0079 (16) |
C15 | 0.045 (2) | 0.046 (2) | 0.054 (2) | 0.0045 (17) | 0.0123 (16) | −0.0004 (17) |
C16 | 0.056 (2) | 0.048 (2) | 0.0375 (18) | 0.0085 (16) | 0.0083 (15) | 0.0017 (15) |
C17 | 0.0304 (16) | 0.0370 (16) | 0.0372 (16) | 0.0018 (14) | 0.0105 (12) | 0.0012 (14) |
C18 | 0.054 (2) | 0.0404 (18) | 0.0377 (17) | 0.0065 (17) | −0.0039 (14) | 0.0006 (15) |
C19 | 0.057 (2) | 0.053 (2) | 0.046 (2) | 0.0138 (18) | 0.0104 (17) | −0.0112 (17) |
Cl | 0.0435 (4) | 0.0432 (4) | 0.0335 (4) | −0.0015 (4) | −0.0042 (3) | 0.0010 (4) |
O3 | 0.092 (2) | 0.0649 (18) | 0.0374 (13) | −0.0005 (15) | 0.0059 (12) | −0.0063 (12) |
O4 | 0.0526 (16) | 0.115 (3) | 0.083 (2) | 0.0114 (17) | −0.0301 (14) | −0.0025 (18) |
O5 | 0.136 (3) | 0.0403 (15) | 0.0669 (18) | 0.0129 (16) | −0.0035 (17) | −0.0051 (13) |
O6 | 0.0661 (17) | 0.089 (2) | 0.0726 (19) | −0.0169 (16) | 0.0220 (14) | 0.0212 (16) |
Geometric parameters (Å, º) top
O1—C2 | 1.351 (3) | C8—C10 | 1.378 (4) |
O1—C10 | 1.397 (3) | C8—H8 | 0.9300 |
O2—C7 | 1.364 (3) | C9—C10 | 1.403 (4) |
O2—C19 | 1.457 (3) | C12—C17 | 1.410 (4) |
N1—C2 | 1.310 (3) | C12—C13 | 1.407 (4) |
N1—H1A | 0.8600 | C13—C14 | 1.384 (4) |
N1—H1B | 0.8600 | C13—H13 | 0.9300 |
N2—C11 | 1.392 (3) | C14—C15 | 1.419 (4) |
N2—C12 | 1.406 (3) | C14—H14 | 0.9300 |
N2—C18 | 1.488 (3) | C15—C16 | 1.389 (4) |
N3—C11 | 1.343 (3) | C15—H15 | 0.9300 |
N3—C17 | 1.399 (4) | C16—C17 | 1.421 (4) |
C2—C3 | 1.467 (4) | C16—H16 | 0.9300 |
C3—C4 | 1.385 (4) | C18—H18A | 0.9600 |
C3—C11 | 1.483 (4) | C18—H18B | 0.9600 |
C4—C9 | 1.426 (4) | C18—H18C | 0.9600 |
C4—H4 | 0.9300 | C19—H19A | 0.9600 |
C5—C6 | 1.384 (4) | C19—H19B | 0.9600 |
C5—C9 | 1.427 (4) | C19—H19C | 0.9600 |
C5—H5 | 0.9300 | Cl—O4 | 1.428 (2) |
C6—C7 | 1.420 (4) | Cl—O3 | 1.440 (2) |
C6—H6 | 0.9300 | Cl—O5 | 1.446 (2) |
C7—C8 | 1.422 (4) | Cl—O6 | 1.450 (3) |
| | | |
C2—O1—C10 | 122.2 (2) | N2—C11—C3 | 126.2 (3) |
C7—O2—C19 | 118.3 (2) | N2—C12—C17 | 105.7 (2) |
C2—N1—H1A | 120.0 | N2—C12—C13 | 132.7 (3) |
C2—N1—H1B | 120.0 | C13—C12—C17 | 121.6 (3) |
H1A—N1—H1B | 120.0 | C14—C13—C12 | 117.1 (3) |
C11—N2—C12 | 106.5 (2) | C14—C13—H13 | 121.5 |
C11—N2—C18 | 130.9 (2) | C12—C13—H13 | 121.5 |
C12—N2—C18 | 122.4 (2) | C13—C14—C15 | 122.1 (3) |
C11—N3—C17 | 105.5 (2) | C13—C14—H14 | 119.0 |
N1—C2—O1 | 113.1 (3) | C15—C14—H14 | 119.0 |
N1—C2—C3 | 125.7 (3) | C16—C15—C14 | 121.3 (3) |
O1—C2—C3 | 121.2 (2) | C16—C15—H15 | 119.4 |
C4—C3—C2 | 115.5 (3) | C14—C15—H15 | 119.4 |
C4—C3—C11 | 126.2 (3) | C15—C16—C17 | 117.2 (3) |
C2—C3—C11 | 118.2 (2) | C15—C16—H16 | 121.4 |
C3—C4—C9 | 123.1 (3) | C17—C16—H16 | 121.4 |
C3—C4—H4 | 118.4 | N3—C17—C12 | 110.1 (3) |
C9—C4—H4 | 118.4 | N3—C17—C16 | 129.1 (3) |
C6—C5—C9 | 120.4 (3) | C12—C17—C16 | 120.7 (3) |
C6—C5—H5 | 119.8 | N2—C18—H18A | 109.5 |
C9—C5—H5 | 119.8 | N2—C18—H18B | 109.5 |
C5—C6—C7 | 120.8 (3) | H18A—C18—H18B | 109.5 |
C5—C6—H6 | 119.6 | N2—C18—H18C | 109.5 |
C7—C6—H6 | 119.6 | H18A—C18—H18C | 109.5 |
O2—C7—C8 | 116.2 (3) | H18B—C18—H18C | 109.5 |
O2—C7—C6 | 124.4 (3) | O2—C19—H19A | 109.5 |
C6—C7—C8 | 119.4 (3) | O2—C19—H19B | 109.5 |
C10—C8—C7 | 118.1 (3) | H19A—C19—H19B | 109.5 |
C10—C8—H8 | 120.9 | O2—C19—H19C | 109.5 |
C7—C8—H8 | 120.9 | H19A—C19—H19C | 109.5 |
C10—C9—C4 | 118.6 (2) | H19B—C19—H19C | 109.5 |
C10—C9—C5 | 117.2 (3) | O4—Cl—O3 | 110.78 (17) |
C4—C9—C5 | 124.2 (3) | O4—Cl—O5 | 110.15 (19) |
C8—C10—O1 | 116.9 (2) | O3—Cl—O5 | 109.83 (15) |
C8—C10—C9 | 124.0 (3) | O4—Cl—O6 | 107.82 (18) |
O1—C10—C9 | 119.2 (2) | O3—Cl—O6 | 108.98 (16) |
N3—C11—N2 | 112.3 (3) | O5—Cl—O6 | 109.2 (2) |
N3—C11—C3 | 121.5 (2) | | |
| | | |
C10—O1—C2—N1 | 175.7 (2) | C17—N3—C11—N2 | 0.2 (3) |
C10—O1—C2—C3 | −4.1 (4) | C17—N3—C11—C3 | 179.7 (2) |
N1—C2—C3—C4 | −174.5 (3) | C12—N2—C11—N3 | 0.2 (3) |
O1—C2—C3—C4 | 5.3 (4) | C18—N2—C11—N3 | 174.5 (3) |
N1—C2—C3—C11 | 3.1 (4) | C12—N2—C11—C3 | −179.3 (3) |
O1—C2—C3—C11 | −177.1 (2) | C18—N2—C11—C3 | −5.0 (5) |
C2—C3—C4—C9 | −3.6 (4) | C4—C3—C11—N3 | 169.0 (3) |
C11—C3—C4—C9 | 179.0 (3) | C2—C3—C11—N3 | −8.3 (4) |
C9—C5—C6—C7 | −0.3 (5) | C4—C3—C11—N2 | −11.6 (5) |
C19—O2—C7—C8 | −178.5 (3) | C2—C3—C11—N2 | 171.1 (3) |
C19—O2—C7—C6 | 2.4 (4) | C11—N2—C12—C17 | −0.5 (3) |
C5—C6—C7—O2 | 179.7 (3) | C18—N2—C12—C17 | −175.4 (2) |
C5—C6—C7—C8 | 0.7 (4) | C11—N2—C12—C13 | −179.8 (3) |
O2—C7—C8—C10 | −179.4 (3) | C18—N2—C12—C13 | 5.4 (5) |
C6—C7—C8—C10 | −0.3 (4) | N2—C12—C13—C14 | −179.8 (3) |
C3—C4—C9—C10 | 0.7 (4) | C17—C12—C13—C14 | 1.0 (4) |
C3—C4—C9—C5 | −179.6 (3) | C12—C13—C14—C15 | 0.0 (5) |
C6—C5—C9—C10 | −0.3 (4) | C13—C14—C15—C16 | 0.1 (5) |
C6—C5—C9—C4 | 180.0 (3) | C14—C15—C16—C17 | −1.1 (5) |
C7—C8—C10—O1 | 179.2 (3) | C11—N3—C17—C12 | −0.5 (3) |
C7—C8—C10—C9 | −0.3 (4) | C11—N3—C17—C16 | −178.2 (3) |
C2—O1—C10—C8 | −178.6 (3) | N2—C12—C17—N3 | 0.6 (3) |
C2—O1—C10—C9 | 0.9 (4) | C13—C12—C17—N3 | 180.0 (3) |
C4—C9—C10—C8 | −179.6 (3) | N2—C12—C17—C16 | 178.5 (3) |
C5—C9—C10—C8 | 0.7 (4) | C13—C12—C17—C16 | −2.1 (4) |
C4—C9—C10—O1 | 0.8 (4) | C15—C16—C17—N3 | 179.5 (3) |
C5—C9—C10—O1 | −178.9 (3) | C15—C16—C17—C12 | 2.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O5 | 0.86 | 2.30 | 3.130 (4) | 163 |
N1—H1B···N3 | 0.86 | 2.01 | 2.665 (4) | 132 |