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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022699/ya6118sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022699/ya6118Isup2.hkl
Contains datablock I

CCDC reference: 203003

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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








Computing details top

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-1H-benzimidazol-2-yl)chromenium perchlorate top
Crystal data top
C18H16N3O2+·ClO4F(000) = 840
Mr = 405.79Dx = 1.520 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.6272 (17) ÅCell parameters from 24 reflections
b = 10.979 (3) Åθ = 11.0–12.0°
c = 18.788 (7) ŵ = 0.26 mm1
β = 94.71 (3)°T = 293 K
V = 1773.5 (9) Å3Complex polyhedron, red
Z = 40.4 × 0.3 × 0.2 mm
Data collection top
Siemens P3/PC
diffractometer
Rint = 0.043
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 2.5°
Graphite monochromatorh = 010
2θ/θ scansk = 013
3526 measured reflectionsl = 2222
3297 independent reflections2 standard reflections every 98 reflections
1992 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-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 reflectionsΔρmax = 0.23 e Å3
256 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.0017xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.2177 (2)0.09447 (18)0.53233 (9)0.0370 (5)
O20.4061 (3)0.2083 (2)0.38248 (11)0.0481 (6)
N10.1405 (3)0.2207 (2)0.61471 (12)0.0435 (7)
H1A0.20880.18540.64360.052*
H1B0.08450.27860.62970.052*
N20.1836 (3)0.4127 (2)0.46649 (12)0.0338 (6)
N30.0873 (3)0.3797 (2)0.58101 (12)0.0373 (6)
C20.1217 (3)0.1862 (3)0.54781 (15)0.0334 (7)
C30.0097 (3)0.2379 (3)0.49303 (14)0.0296 (6)
C40.0008 (3)0.1797 (3)0.42742 (15)0.0354 (7)
H40.07280.20660.39200.042*
C50.0930 (3)0.0197 (3)0.34432 (15)0.0402 (7)
H50.02120.04450.30750.048*
C60.1930 (3)0.0758 (3)0.33348 (15)0.0408 (7)
H60.18730.11500.28950.049*
C70.3041 (3)0.1147 (3)0.38878 (16)0.0365 (7)
C80.3112 (3)0.0554 (3)0.45627 (15)0.0373 (7)
H80.38270.07960.49330.045*
C90.0993 (3)0.0806 (3)0.41163 (14)0.0314 (6)
C100.2093 (3)0.0390 (3)0.46522 (14)0.0323 (7)
C110.0868 (3)0.3423 (3)0.51298 (15)0.0320 (6)
C120.2499 (3)0.5016 (3)0.50854 (15)0.0316 (6)
C130.3558 (3)0.5969 (3)0.49194 (17)0.0412 (7)
H130.39680.61090.44530.049*
C140.3963 (4)0.6687 (3)0.54801 (17)0.0448 (8)
H140.46610.73240.53860.054*
C150.3347 (4)0.6483 (3)0.61938 (18)0.0482 (9)
H150.36500.69860.65550.058*
C160.2299 (4)0.5545 (3)0.63627 (17)0.0469 (8)
H160.18800.54190.68290.056*
C170.1893 (3)0.4788 (3)0.57931 (15)0.0344 (7)
C180.2094 (4)0.4112 (3)0.38722 (15)0.0446 (8)
H18A0.11110.40510.36700.067*
H18B0.26060.48500.37110.067*
H18C0.27300.34260.37240.067*
C190.4059 (4)0.2701 (3)0.31384 (16)0.0519 (9)
H19A0.30540.30540.30170.078*
H19B0.48330.33310.31690.078*
H19C0.42880.21250.27770.078*
Cl0.36755 (9)0.08682 (7)0.70706 (4)0.0405 (2)
O30.3694 (3)0.1181 (2)0.63269 (11)0.0646 (7)
O40.5102 (3)0.1211 (3)0.74588 (14)0.0854 (10)
O50.3416 (4)0.0426 (2)0.71428 (14)0.0817 (9)
O60.2427 (3)0.1529 (3)0.73705 (14)0.0749 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0438 (12)0.0351 (11)0.0308 (10)0.0063 (10)0.0043 (9)0.0023 (9)
O20.0522 (15)0.0495 (14)0.0424 (13)0.0171 (11)0.0032 (11)0.0046 (11)
N10.0512 (17)0.0482 (17)0.0299 (14)0.0090 (14)0.0034 (12)0.0010 (12)
N20.0320 (13)0.0369 (14)0.0325 (13)0.0012 (12)0.0022 (10)0.0018 (12)
N30.0400 (15)0.0419 (15)0.0303 (13)0.0055 (12)0.0045 (11)0.0015 (11)
C20.0353 (17)0.0302 (16)0.0352 (16)0.0068 (13)0.0067 (13)0.0011 (13)
C30.0301 (15)0.0306 (15)0.0282 (14)0.0034 (13)0.0032 (12)0.0041 (12)
C40.0328 (16)0.0379 (17)0.0343 (16)0.0009 (14)0.0042 (13)0.0007 (13)
C50.0367 (18)0.0435 (18)0.0396 (17)0.0054 (15)0.0026 (14)0.0007 (15)
C60.0419 (18)0.0460 (18)0.0342 (16)0.0009 (16)0.0019 (13)0.0005 (15)
C70.0361 (17)0.0349 (18)0.0394 (17)0.0025 (13)0.0081 (13)0.0020 (13)
C80.0387 (18)0.0338 (17)0.0384 (17)0.0005 (13)0.0034 (13)0.0040 (13)
C90.0301 (15)0.0314 (15)0.0326 (15)0.0003 (13)0.0014 (12)0.0019 (13)
C100.0348 (16)0.0327 (16)0.0293 (15)0.0010 (13)0.0015 (12)0.0001 (12)
C110.0309 (16)0.0287 (15)0.0362 (16)0.0035 (12)0.0025 (13)0.0003 (13)
C120.0252 (15)0.0299 (15)0.0396 (16)0.0041 (12)0.0022 (12)0.0031 (13)
C130.0346 (17)0.0391 (18)0.0496 (19)0.0001 (15)0.0019 (14)0.0038 (16)
C140.0392 (19)0.0349 (17)0.061 (2)0.0076 (15)0.0099 (16)0.0079 (16)
C150.045 (2)0.046 (2)0.054 (2)0.0045 (17)0.0123 (16)0.0004 (17)
C160.056 (2)0.048 (2)0.0375 (18)0.0085 (16)0.0083 (15)0.0017 (15)
C170.0304 (16)0.0370 (16)0.0372 (16)0.0018 (14)0.0105 (12)0.0012 (14)
C180.054 (2)0.0404 (18)0.0377 (17)0.0065 (17)0.0039 (14)0.0006 (15)
C190.057 (2)0.053 (2)0.046 (2)0.0138 (18)0.0104 (17)0.0112 (17)
Cl0.0435 (4)0.0432 (4)0.0335 (4)0.0015 (4)0.0042 (3)0.0010 (4)
O30.092 (2)0.0649 (18)0.0374 (13)0.0005 (15)0.0059 (12)0.0063 (12)
O40.0526 (16)0.115 (3)0.083 (2)0.0114 (17)0.0301 (14)0.0025 (18)
O50.136 (3)0.0403 (15)0.0669 (18)0.0129 (16)0.0035 (17)0.0051 (13)
O60.0661 (17)0.089 (2)0.0726 (19)0.0169 (16)0.0220 (14)0.0212 (16)
Geometric parameters (Å, º) top
O1—C21.351 (3)C8—C101.378 (4)
O1—C101.397 (3)C8—H80.9300
O2—C71.364 (3)C9—C101.403 (4)
O2—C191.457 (3)C12—C171.410 (4)
N1—C21.310 (3)C12—C131.407 (4)
N1—H1A0.8600C13—C141.384 (4)
N1—H1B0.8600C13—H130.9300
N2—C111.392 (3)C14—C151.419 (4)
N2—C121.406 (3)C14—H140.9300
N2—C181.488 (3)C15—C161.389 (4)
N3—C111.343 (3)C15—H150.9300
N3—C171.399 (4)C16—C171.421 (4)
C2—C31.467 (4)C16—H160.9300
C3—C41.385 (4)C18—H18A0.9600
C3—C111.483 (4)C18—H18B0.9600
C4—C91.426 (4)C18—H18C0.9600
C4—H40.9300C19—H19A0.9600
C5—C61.384 (4)C19—H19B0.9600
C5—C91.427 (4)C19—H19C0.9600
C5—H50.9300Cl—O41.428 (2)
C6—C71.420 (4)Cl—O31.440 (2)
C6—H60.9300Cl—O51.446 (2)
C7—C81.422 (4)Cl—O61.450 (3)
C2—O1—C10122.2 (2)N2—C11—C3126.2 (3)
C7—O2—C19118.3 (2)N2—C12—C17105.7 (2)
C2—N1—H1A120.0N2—C12—C13132.7 (3)
C2—N1—H1B120.0C13—C12—C17121.6 (3)
H1A—N1—H1B120.0C14—C13—C12117.1 (3)
C11—N2—C12106.5 (2)C14—C13—H13121.5
C11—N2—C18130.9 (2)C12—C13—H13121.5
C12—N2—C18122.4 (2)C13—C14—C15122.1 (3)
C11—N3—C17105.5 (2)C13—C14—H14119.0
N1—C2—O1113.1 (3)C15—C14—H14119.0
N1—C2—C3125.7 (3)C16—C15—C14121.3 (3)
O1—C2—C3121.2 (2)C16—C15—H15119.4
C4—C3—C2115.5 (3)C14—C15—H15119.4
C4—C3—C11126.2 (3)C15—C16—C17117.2 (3)
C2—C3—C11118.2 (2)C15—C16—H16121.4
C3—C4—C9123.1 (3)C17—C16—H16121.4
C3—C4—H4118.4N3—C17—C12110.1 (3)
C9—C4—H4118.4N3—C17—C16129.1 (3)
C6—C5—C9120.4 (3)C12—C17—C16120.7 (3)
C6—C5—H5119.8N2—C18—H18A109.5
C9—C5—H5119.8N2—C18—H18B109.5
C5—C6—C7120.8 (3)H18A—C18—H18B109.5
C5—C6—H6119.6N2—C18—H18C109.5
C7—C6—H6119.6H18A—C18—H18C109.5
O2—C7—C8116.2 (3)H18B—C18—H18C109.5
O2—C7—C6124.4 (3)O2—C19—H19A109.5
C6—C7—C8119.4 (3)O2—C19—H19B109.5
C10—C8—C7118.1 (3)H19A—C19—H19B109.5
C10—C8—H8120.9O2—C19—H19C109.5
C7—C8—H8120.9H19A—C19—H19C109.5
C10—C9—C4118.6 (2)H19B—C19—H19C109.5
C10—C9—C5117.2 (3)O4—Cl—O3110.78 (17)
C4—C9—C5124.2 (3)O4—Cl—O5110.15 (19)
C8—C10—O1116.9 (2)O3—Cl—O5109.83 (15)
C8—C10—C9124.0 (3)O4—Cl—O6107.82 (18)
O1—C10—C9119.2 (2)O3—Cl—O6108.98 (16)
N3—C11—N2112.3 (3)O5—Cl—O6109.2 (2)
N3—C11—C3121.5 (2)
C10—O1—C2—N1175.7 (2)C17—N3—C11—N20.2 (3)
C10—O1—C2—C34.1 (4)C17—N3—C11—C3179.7 (2)
N1—C2—C3—C4174.5 (3)C12—N2—C11—N30.2 (3)
O1—C2—C3—C45.3 (4)C18—N2—C11—N3174.5 (3)
N1—C2—C3—C113.1 (4)C12—N2—C11—C3179.3 (3)
O1—C2—C3—C11177.1 (2)C18—N2—C11—C35.0 (5)
C2—C3—C4—C93.6 (4)C4—C3—C11—N3169.0 (3)
C11—C3—C4—C9179.0 (3)C2—C3—C11—N38.3 (4)
C9—C5—C6—C70.3 (5)C4—C3—C11—N211.6 (5)
C19—O2—C7—C8178.5 (3)C2—C3—C11—N2171.1 (3)
C19—O2—C7—C62.4 (4)C11—N2—C12—C170.5 (3)
C5—C6—C7—O2179.7 (3)C18—N2—C12—C17175.4 (2)
C5—C6—C7—C80.7 (4)C11—N2—C12—C13179.8 (3)
O2—C7—C8—C10179.4 (3)C18—N2—C12—C135.4 (5)
C6—C7—C8—C100.3 (4)N2—C12—C13—C14179.8 (3)
C3—C4—C9—C100.7 (4)C17—C12—C13—C141.0 (4)
C3—C4—C9—C5179.6 (3)C12—C13—C14—C150.0 (5)
C6—C5—C9—C100.3 (4)C13—C14—C15—C160.1 (5)
C6—C5—C9—C4180.0 (3)C14—C15—C16—C171.1 (5)
C7—C8—C10—O1179.2 (3)C11—N3—C17—C120.5 (3)
C7—C8—C10—C90.3 (4)C11—N3—C17—C16178.2 (3)
C2—O1—C10—C8178.6 (3)N2—C12—C17—N30.6 (3)
C2—O1—C10—C90.9 (4)C13—C12—C17—N3180.0 (3)
C4—C9—C10—C8179.6 (3)N2—C12—C17—C16178.5 (3)
C5—C9—C10—C80.7 (4)C13—C12—C17—C162.1 (4)
C4—C9—C10—O10.8 (4)C15—C16—C17—N3179.5 (3)
C5—C9—C10—O1178.9 (3)C15—C16—C17—C122.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O50.862.303.130 (4)163
N1—H1B···N30.862.012.665 (4)132
 

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