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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2622.
Published online 2009 October 3. doi:  10.1107/S1600536809039439
PMCID: PMC2971138

9-Benzamido­acridinium chloride

Abstract

In the title compound, C20H15N2O+·Cl, the dihedral angle between the fused-ring system and the benzene ring is 63.10 (7)°. In the crystal, N—H(...)Cl hydrogen bonds link the components and aromatic π–π stacking [shortest centroid–centroid distance = 3.6421 (12) Å] occurs.

Related literature

For background to acridine derivatives, see: Antonini (2002 [triangle]); Carvalho et al. (2005 [triangle]). For the synthesis, see: He et al. (2008 [triangle]); Chandregowda et al. (2009 [triangle]). For related structures, see: Sikorski et al. (2007 [triangle], 2008 [triangle]); Trzybiníski et al. (2009 [triangle]).

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Object name is e-65-o2622-scheme1.jpg

Experimental

Crystal data

  • C20H15N2O+·Cl
  • M r = 334.79
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2622-efi1.jpg
  • a = 8.9601 (17) Å
  • b = 9.0084 (17) Å
  • c = 10.8775 (18) Å
  • α = 79.168 (7)°
  • β = 65.855 (5)°
  • γ = 86.927 (7)°
  • V = 786.6 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 93 K
  • 0.37 × 0.33 × 0.17 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.913, T max = 0.959
  • 4772 measured reflections
  • 2955 independent reflections
  • 2538 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.069
  • S = 1.00
  • 2955 reflections
  • 225 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039439/hb5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039439/hb5083Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of the Sichuan Education Department (grant No. 2006B039).

supplementary crystallographic information

Comment

Acridine derivatives which show strong antiproliferative activities on human transformed cells, have been considered as promising agents for anticancer and antiparasitic therapy (Antonini et al., 2002) in recent years. Meanwhile Complexes containing acridine moiety are interesting in luminescence study (Carvalho et al., 2005). Therefore they attract more and more chemists' attention. Here we report the synthesis and crystal structure of the title compound (Fig. 1).

the bond lengths and angles characterizing the geometry of the acridinium moiety are typical of acridine-based derivatives (Sikorski et al., 2007, 2008). Atoms N2/C14/O1 which form dihedral angles with n1/c1/c6/c13/c12/c7 plane and c15 - c20 ring of 55.48 (1) Å and 6.82 (3) Å, respectively,are coplaner. The dihedral angle between the n1/c1/c6/c13/c12/c7 ring and c15 - c20 plane is 61.76 (6) Å.

In the crystal structure, weak Cl—H···N hydrogen bonds link the two cations and anions in ion pairs. π-π interactions between n1/c1/c6/c13/c12/c7 ring and c1-c6 ring are observed, with a Cg1···Cg2 distance of 3.6234 Å. [symmetry code: (i) –X,-1-Y,-Z] Where Cg1 and Cg2 are n1/c1/c6/c13/c12/c7 and c1-c6 centroid, respectively (Table 1).

Experimental

The title compound was prepared according to the reported procedure of He et al.. (2008) & Chandregowda et al.. (2009). Yellow chunks of (I) were obtained by recrystallization from methanol.

Refinement

H atoms were placed in calculated positions with C—H = 0.95–0.99 Å, & N—H = 0.9025–0.9390 Å and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Crystal data

C20H15N2O+·ClZ = 2
Mr = 334.79F(000) = 348
Triclinic, P1Dx = 1.413 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9601 (17) ÅCell parameters from 2420 reflections
b = 9.0084 (17) Åθ = 3.2–27.5°
c = 10.8775 (18) ŵ = 0.25 mm1
α = 79.168 (7)°T = 93 K
β = 65.855 (5)°Chunk, yellow
γ = 86.927 (7)°0.37 × 0.33 × 0.17 mm
V = 786.6 (2) Å3

Data collection

Rigaku SPIDER diffractometer2955 independent reflections
Radiation source: Rotating Anode2538 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→11
Tmin = 0.913, Tmax = 0.959k = −10→11
4772 measured reflectionsl = −12→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0136P)2 + 0.516P] where P = (Fo2 + 2Fc2)/3
2955 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

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)

xyzUiso*/Ueq
Cl10.78153 (5)0.85506 (5)−0.03376 (4)0.01909 (12)
O10.39684 (14)0.63975 (13)0.49853 (12)0.0187 (3)
N10.34182 (17)0.35116 (16)0.16256 (14)0.0143 (3)
N20.54610 (18)0.68607 (16)0.26770 (15)0.0153 (3)
C10.5768 (2)0.46569 (18)0.16353 (17)0.0139 (4)
C20.7475 (2)0.45912 (19)0.13000 (17)0.0161 (4)
H20.79880.53170.15410.019*
C30.8384 (2)0.34982 (19)0.06364 (18)0.0178 (4)
H30.95240.34690.04220.021*
C40.7652 (2)0.2403 (2)0.02605 (18)0.0185 (4)
H40.83060.1652−0.02050.022*
C50.6021 (2)0.24183 (19)0.05601 (17)0.0165 (4)
H50.55380.16870.03010.020*
C60.5053 (2)0.35355 (18)0.12623 (17)0.0142 (4)
C70.2393 (2)0.44990 (18)0.23448 (17)0.0140 (4)
C80.0696 (2)0.4369 (2)0.27045 (18)0.0176 (4)
H80.02680.35670.24780.021*
C9−0.0322 (2)0.5401 (2)0.33778 (18)0.0194 (4)
H9−0.14680.52970.36490.023*
C100.0313 (2)0.6631 (2)0.36779 (18)0.0197 (4)
H10−0.04060.73720.41060.024*
C110.1935 (2)0.67615 (19)0.33612 (18)0.0172 (4)
H110.23380.75920.35710.021*
C120.3043 (2)0.56678 (18)0.27180 (17)0.0141 (4)
C130.4735 (2)0.57227 (18)0.23643 (17)0.0139 (4)
C140.5083 (2)0.70877 (18)0.39917 (18)0.0145 (4)
C150.6172 (2)0.82148 (18)0.41153 (17)0.0139 (4)
C160.7367 (2)0.91166 (19)0.30042 (18)0.0175 (4)
H160.75280.90470.20980.021*
C170.8326 (2)1.01193 (19)0.32150 (19)0.0198 (4)
H170.91401.07350.24530.024*
C180.8099 (2)1.02228 (19)0.45330 (19)0.0187 (4)
H180.87651.09020.46740.022*
C190.6903 (2)0.93372 (19)0.56455 (19)0.0190 (4)
H190.67460.94120.65500.023*
C200.5936 (2)0.83416 (19)0.54403 (18)0.0165 (4)
H200.51090.77430.62060.020*
H1N0.298 (2)0.278 (2)0.1340 (19)0.023 (5)*
H2N0.633 (2)0.736 (2)0.197 (2)0.024 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0200 (2)0.0198 (2)0.0173 (2)−0.00404 (17)−0.00573 (19)−0.00612 (18)
O10.0190 (7)0.0196 (6)0.0160 (7)−0.0045 (5)−0.0056 (6)−0.0020 (5)
N10.0175 (8)0.0134 (7)0.0137 (8)−0.0022 (6)−0.0077 (6)−0.0023 (6)
N20.0160 (8)0.0165 (8)0.0128 (8)−0.0038 (6)−0.0040 (7)−0.0045 (6)
C10.0177 (9)0.0131 (8)0.0103 (9)−0.0006 (7)−0.0060 (7)−0.0001 (7)
C20.0183 (9)0.0165 (9)0.0147 (9)−0.0034 (7)−0.0083 (8)−0.0011 (7)
C30.0164 (10)0.0183 (9)0.0166 (10)0.0015 (7)−0.0058 (8)−0.0008 (8)
C40.0230 (10)0.0168 (9)0.0139 (9)0.0029 (7)−0.0062 (8)−0.0027 (7)
C50.0228 (10)0.0141 (9)0.0143 (9)−0.0002 (7)−0.0090 (8)−0.0029 (7)
C60.0175 (10)0.0143 (8)0.0102 (9)−0.0022 (7)−0.0061 (7)0.0010 (7)
C70.0175 (9)0.0139 (8)0.0104 (9)−0.0008 (7)−0.0061 (7)−0.0004 (7)
C80.0194 (10)0.0198 (9)0.0155 (9)−0.0030 (7)−0.0094 (8)−0.0018 (8)
C90.0144 (9)0.0277 (10)0.0166 (9)−0.0007 (8)−0.0074 (8)−0.0028 (8)
C100.0203 (10)0.0234 (10)0.0159 (10)0.0054 (8)−0.0077 (8)−0.0055 (8)
C110.0215 (10)0.0169 (9)0.0156 (9)0.0009 (7)−0.0096 (8)−0.0039 (8)
C120.0170 (9)0.0143 (8)0.0109 (9)−0.0013 (7)−0.0060 (7)−0.0007 (7)
C130.0188 (10)0.0126 (8)0.0101 (8)−0.0030 (7)−0.0064 (7)0.0004 (7)
C140.0159 (9)0.0130 (8)0.0166 (9)0.0033 (7)−0.0085 (8)−0.0040 (7)
C150.0148 (9)0.0121 (8)0.0169 (9)0.0024 (7)−0.0078 (8)−0.0045 (7)
C160.0202 (10)0.0186 (9)0.0150 (9)−0.0005 (7)−0.0070 (8)−0.0058 (8)
C170.0201 (10)0.0181 (9)0.0187 (10)−0.0039 (8)−0.0044 (8)−0.0042 (8)
C180.0200 (10)0.0164 (9)0.0238 (10)0.0003 (7)−0.0118 (8)−0.0064 (8)
C190.0261 (10)0.0183 (9)0.0171 (10)0.0026 (8)−0.0123 (8)−0.0063 (8)
C200.0205 (10)0.0141 (8)0.0150 (9)−0.0002 (7)−0.0077 (8)−0.0015 (7)

Geometric parameters (Å, °)

O1—C141.218 (2)C8—H80.9500
N1—C61.352 (2)C9—C101.419 (2)
N1—C71.354 (2)C9—H90.9500
N1—H1N0.939 (19)C10—C111.356 (2)
N2—C141.381 (2)C10—H100.9500
N2—C131.405 (2)C11—C121.425 (2)
N2—H2N0.902 (19)C11—H110.9500
C1—C131.414 (2)C12—C131.404 (2)
C1—C21.421 (2)C14—C151.505 (2)
C1—C61.425 (2)C15—C161.390 (2)
C2—C31.362 (2)C15—C201.395 (2)
C2—H20.9500C16—C171.389 (2)
C3—C41.418 (2)C16—H160.9500
C3—H30.9500C17—C181.384 (2)
C4—C51.360 (2)C17—H170.9500
C4—H40.9500C18—C191.385 (2)
C5—C61.415 (2)C18—H180.9500
C5—H50.9500C19—C201.387 (2)
C7—C81.412 (2)C19—H190.9500
C7—C121.426 (2)C20—H200.9500
C8—C91.361 (2)
C6—N1—C7123.57 (14)C11—C10—C9120.77 (16)
C6—N1—H1N117.6 (11)C11—C10—H10119.6
C7—N1—H1N118.8 (11)C9—C10—H10119.6
C14—N2—C13124.05 (15)C10—C11—C12120.82 (16)
C14—N2—H2N120.0 (12)C10—C11—H11119.6
C13—N2—H2N115.3 (12)C12—C11—H11119.6
C13—C1—C2123.94 (15)C13—C12—C11124.12 (15)
C13—C1—C6118.42 (15)C13—C12—C7118.46 (15)
C2—C1—C6117.58 (15)C11—C12—C7117.32 (15)
C3—C2—C1120.64 (16)C12—C13—N2121.44 (15)
C3—C2—H2119.7C12—C13—C1120.60 (15)
C1—C2—H2119.7N2—C13—C1117.93 (15)
C2—C3—C4120.88 (17)O1—C14—N2122.22 (15)
C2—C3—H3119.6O1—C14—C15122.34 (15)
C4—C3—H3119.6N2—C14—C15115.42 (15)
C5—C4—C3120.67 (16)C16—C15—C20119.27 (15)
C5—C4—H4119.7C16—C15—C14124.14 (15)
C3—C4—H4119.7C20—C15—C14116.59 (15)
C4—C5—C6119.29 (16)C17—C16—C15120.21 (16)
C4—C5—H5120.4C17—C16—H16119.9
C6—C5—H5120.4C15—C16—H16119.9
N1—C6—C5119.64 (15)C18—C17—C16120.14 (17)
N1—C6—C1119.40 (15)C18—C17—H17119.9
C5—C6—C1120.93 (16)C16—C17—H17119.9
N1—C7—C8119.67 (15)C17—C18—C19120.02 (16)
N1—C7—C12119.52 (15)C17—C18—H18120.0
C8—C7—C12120.81 (15)C19—C18—H18120.0
C9—C8—C7119.44 (16)C18—C19—C20120.04 (16)
C9—C8—H8120.3C18—C19—H19120.0
C7—C8—H8120.3C20—C19—H19120.0
C8—C9—C10120.61 (17)C19—C20—C15120.31 (16)
C8—C9—H9119.7C19—C20—H20119.8
C10—C9—H9119.7C15—C20—H20119.8
C13—C1—C2—C3177.69 (17)C8—C7—C12—C11−5.1 (2)
C6—C1—C2—C30.5 (3)C11—C12—C13—N22.5 (3)
C1—C2—C3—C40.2 (3)C7—C12—C13—N2178.76 (16)
C2—C3—C4—C5−0.2 (3)C11—C12—C13—C1−175.20 (17)
C3—C4—C5—C6−0.4 (3)C7—C12—C13—C11.0 (2)
C7—N1—C6—C5177.34 (16)C14—N2—C13—C1261.0 (2)
C7—N1—C6—C1−0.5 (2)C14—N2—C13—C1−121.22 (18)
C4—C5—C6—N1−176.64 (16)C2—C1—C13—C12−176.74 (16)
C4—C5—C6—C11.2 (3)C6—C1—C13—C120.4 (2)
C13—C1—C6—N1−0.7 (2)C2—C1—C13—N25.4 (3)
C2—C1—C6—N1176.61 (16)C6—C1—C13—N2−177.42 (15)
C13—C1—C6—C5−178.53 (16)C13—N2—C14—O1−7.0 (3)
C2—C1—C6—C5−1.2 (2)C13—N2—C14—C15171.42 (15)
C6—N1—C7—C8−178.65 (16)O1—C14—C15—C16−174.41 (17)
C6—N1—C7—C122.0 (3)N2—C14—C15—C167.1 (2)
N1—C7—C8—C9−177.30 (17)O1—C14—C15—C205.4 (2)
C12—C7—C8—C92.1 (3)N2—C14—C15—C20−173.03 (15)
C7—C8—C9—C102.2 (3)C20—C15—C16—C170.7 (3)
C8—C9—C10—C11−3.3 (3)C14—C15—C16—C17−179.45 (16)
C9—C10—C11—C120.1 (3)C15—C16—C17—C180.2 (3)
C10—C11—C12—C13−179.75 (17)C16—C17—C18—C19−0.7 (3)
C10—C11—C12—C74.0 (3)C17—C18—C19—C200.2 (3)
N1—C7—C12—C13−2.2 (2)C18—C19—C20—C150.6 (3)
C8—C7—C12—C13178.44 (16)C16—C15—C20—C19−1.1 (3)
N1—C7—C12—C11174.28 (15)C14—C15—C20—C19179.04 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl1i0.93 (2)2.09 (2)3.0167 (17)168 (8)
N2—H2N···Cl10.90 (2)2.37 (2)3.2139 (17)154 (4)

Symmetry codes: (i) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5083).

References

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