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In the triclinic crystalline phase of the title compound, C22H18NO2+·CF3O3S, the mean planes of the acridine ring systems lie parallel to each other. The benzene rings are also parallel. However, the acridine system and benzene ring in each cation are inclined at an angle of 28.5 (1)°, and the acridine system and carboxyl group are at an angle of 87.8 (2)° to each other. The structure is stabilized by C—H...O and C—H...π hydrogen bonds and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002340/ac6227sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002340/ac6227Isup2.hkl
Contains datablock I

CCDC reference: 298354

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.067
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT480_ALERT_4_B Long H...A H-Bond Reported H6 .. CG3 .. 3.36 Ang. PLAT480_ALERT_4_B Long H...A H-Bond Reported H21 .. CG3 .. 3.38 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S26 - O27 .. 6.56 su PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S26 - O28 .. 5.77 su PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S26 - C30 .. 5.47 su PLAT412_ALERT_2_C Short Intra XH3 .. XHn H4 .. H25C .. 1.82 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C6 .. C6 .. 3.18 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. CG4 .. 3.08 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; 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 and PLATON (Spek, 2003).

10-Methyl-9-(2-methylphenoxycarbonyl)acridinium trifluoromethanesulfonate top
Crystal data top
C22H18NO2+·CF3O3SZ = 2
Mr = 477.45F(000) = 492
Triclinic, P1Dx = 1.527 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.160 (2) ÅCell parameters from 5975 reflections
b = 10.558 (2) Åθ = 3.1–25.0°
c = 11.060 (2) ŵ = 0.22 mm1
α = 80.35 (3)°T = 100 K
β = 87.87 (3)°Needle, pale yellow
γ = 80.03 (3)°0.30 × 0.15 × 0.10 mm
V = 1038.5 (4) Å3
Data collection top
Kuma KM-4-CCD κ-geometry
diffractometer
2437 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 25.0°, θmin = 3.1°
ω scansh = 910
6626 measured reflectionsk = 1112
3564 independent reflectionsl = 1312
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0245P)2]
where P = (Fo2 + 2Fc2)/3
3564 reflections(Δ/σ)max < 0.001
300 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.31 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1863 (2)0.99908 (18)0.03961 (19)0.0171 (5)
H10.19051.07890.06700.020*
C20.1941 (2)0.99397 (18)0.08144 (19)0.0173 (5)
H20.20351.07000.13880.021*
C30.1884 (2)0.87546 (18)0.12311 (19)0.0196 (5)
H30.19430.87300.20860.024*
C40.1746 (2)0.76458 (19)0.04336 (18)0.0184 (5)
H40.17000.68630.07360.022*
C50.1632 (2)0.53996 (19)0.37890 (19)0.0202 (5)
H50.17270.45830.35150.024*
C60.1566 (2)0.5451 (2)0.5011 (2)0.0233 (5)
H60.16480.46600.55780.028*
C70.1378 (2)0.66492 (19)0.5464 (2)0.0232 (5)
H70.12680.66670.63190.028*
C80.1359 (2)0.77690 (19)0.46552 (18)0.0197 (5)
H80.12580.85730.49540.024*
C90.1629 (2)0.88846 (18)0.25279 (18)0.0154 (5)
N100.16051 (16)0.65533 (14)0.16876 (15)0.0157 (4)
C110.1716 (2)0.88606 (18)0.12721 (18)0.0149 (5)
C120.1671 (2)0.76625 (18)0.08407 (18)0.0140 (5)
C130.1488 (2)0.77680 (18)0.33759 (18)0.0157 (5)
C140.1560 (2)0.65632 (18)0.29237 (19)0.0170 (5)
C150.1769 (2)1.01267 (19)0.29875 (17)0.0166 (5)
O160.32269 (14)1.01472 (12)0.30869 (12)0.0194 (3)
O170.07683 (15)1.09417 (13)0.32196 (13)0.0241 (4)
C180.3684 (2)1.12662 (18)0.34204 (19)0.0192 (5)
C190.3583 (2)1.14740 (19)0.46204 (19)0.0202 (5)
C200.4221 (2)1.25166 (19)0.4882 (2)0.0250 (5)
H200.41741.27050.56940.030*
C210.4915 (2)1.3270 (2)0.3972 (2)0.0260 (5)
H210.53421.39660.41710.031*
C220.4999 (2)1.30342 (19)0.2782 (2)0.0254 (5)
H220.54781.35630.21670.031*
C230.4377 (2)1.20130 (19)0.2490 (2)0.0230 (5)
H230.44251.18300.16760.028*
C240.2861 (2)1.06340 (19)0.56189 (19)0.0263 (5)
H24A0.31431.07900.64200.040*
H24B0.31890.97140.55520.040*
H24C0.17821.08500.55350.040*
C250.1626 (2)0.53008 (17)0.12404 (19)0.0220 (5)
H25A0.09380.48060.17340.033*
H25B0.26300.47930.13120.033*
H25C0.13230.54760.03800.033*
S260.23257 (6)0.36221 (5)0.84983 (5)0.01791 (14)
O270.17644 (15)0.31158 (12)0.96862 (12)0.0213 (3)
O280.21171 (15)0.50317 (12)0.82054 (12)0.0229 (4)
O290.20178 (14)0.29779 (12)0.75065 (12)0.0225 (4)
C300.4331 (2)0.3167 (2)0.8671 (2)0.0231 (5)
F310.47393 (13)0.18848 (11)0.89992 (12)0.0391 (4)
F320.48232 (13)0.37370 (12)0.95377 (11)0.0359 (3)
F330.50550 (13)0.35291 (12)0.76367 (11)0.0342 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0159 (11)0.0117 (11)0.0238 (13)0.0026 (9)0.0000 (9)0.0031 (9)
C20.0176 (12)0.0149 (11)0.0176 (13)0.0023 (9)0.0003 (9)0.0024 (9)
C30.0191 (12)0.0231 (12)0.0166 (12)0.0024 (10)0.0013 (9)0.0041 (10)
C40.0173 (12)0.0177 (12)0.0211 (13)0.0035 (9)0.0015 (9)0.0049 (10)
C50.0180 (12)0.0169 (12)0.0253 (14)0.0045 (9)0.0007 (10)0.0002 (10)
C60.0176 (12)0.0238 (13)0.0250 (14)0.0037 (10)0.0014 (10)0.0062 (10)
C70.0183 (12)0.0299 (13)0.0198 (13)0.0039 (10)0.0013 (9)0.0004 (10)
C80.0180 (12)0.0208 (12)0.0200 (13)0.0032 (9)0.0010 (9)0.0031 (10)
C90.0102 (11)0.0160 (11)0.0201 (13)0.0011 (9)0.0001 (9)0.0047 (9)
N100.0160 (10)0.0115 (9)0.0195 (11)0.0028 (7)0.0007 (8)0.0021 (8)
C110.0092 (11)0.0150 (11)0.0194 (12)0.0012 (8)0.0013 (9)0.0030 (9)
C120.0091 (11)0.0149 (11)0.0172 (12)0.0011 (8)0.0009 (9)0.0012 (9)
C130.0106 (11)0.0202 (12)0.0162 (12)0.0016 (9)0.0000 (9)0.0039 (9)
C140.0118 (11)0.0194 (12)0.0194 (13)0.0035 (9)0.0003 (9)0.0013 (9)
C150.0221 (13)0.0198 (12)0.0075 (11)0.0044 (10)0.0022 (9)0.0002 (9)
O160.0170 (8)0.0192 (8)0.0245 (9)0.0043 (6)0.0002 (6)0.0096 (6)
O170.0207 (9)0.0223 (8)0.0300 (9)0.0021 (7)0.0019 (7)0.0116 (7)
C180.0158 (12)0.0183 (11)0.0247 (13)0.0016 (9)0.0043 (9)0.0076 (10)
C190.0184 (12)0.0210 (12)0.0203 (13)0.0009 (9)0.0007 (9)0.0052 (10)
C200.0233 (13)0.0268 (13)0.0253 (13)0.0034 (10)0.0052 (10)0.0124 (11)
C210.0184 (13)0.0224 (12)0.0382 (15)0.0005 (10)0.0048 (11)0.0098 (11)
C220.0205 (13)0.0203 (12)0.0348 (15)0.0030 (10)0.0002 (10)0.0029 (10)
C230.0183 (12)0.0239 (13)0.0264 (13)0.0015 (10)0.0007 (10)0.0054 (10)
C240.0294 (14)0.0293 (13)0.0206 (13)0.0028 (10)0.0009 (10)0.0071 (10)
C250.0300 (13)0.0156 (12)0.0224 (13)0.0055 (10)0.0004 (10)0.0070 (9)
S260.0183 (3)0.0150 (3)0.0205 (3)0.0030 (2)0.0008 (2)0.0026 (2)
O270.0254 (8)0.0183 (8)0.0190 (8)0.0050 (6)0.0058 (7)0.0002 (6)
O280.0325 (9)0.0099 (8)0.0246 (9)0.0016 (6)0.0002 (7)0.0001 (6)
O290.0262 (9)0.0223 (8)0.0216 (8)0.0063 (7)0.0039 (7)0.0078 (7)
C300.0252 (13)0.0225 (13)0.0241 (14)0.0079 (10)0.0002 (11)0.0071 (10)
F310.0269 (8)0.0249 (8)0.0603 (10)0.0065 (6)0.0058 (7)0.0025 (7)
F320.0293 (8)0.0492 (8)0.0337 (8)0.0114 (6)0.0092 (6)0.0129 (7)
F330.0247 (7)0.0499 (8)0.0313 (8)0.0148 (6)0.0090 (6)0.0095 (6)
Geometric parameters (Å, º) top
C1—C21.348 (3)C15—O171.196 (2)
C1—C111.428 (2)O16—C181.427 (2)
C1—H10.9500C18—C191.378 (3)
C2—C31.414 (3)C18—C231.392 (3)
C2—H20.9500C19—C201.407 (3)
C3—C41.364 (3)C19—C241.504 (3)
C3—H30.9500C20—C211.382 (3)
C4—C121.411 (3)C20—H200.9500
C4—H40.9500C21—C221.376 (3)
C5—C61.360 (3)C21—H210.9500
C5—C141.418 (3)C22—C231.391 (3)
C5—H50.9500C22—H220.9500
C6—C71.418 (3)C23—H230.9500
C6—H60.9500C24—H24A0.9800
C7—C81.356 (3)C24—H24B0.9800
C7—H70.9500C24—H24C0.9800
C8—C131.416 (3)C25—H25A0.9800
C8—H80.9500C25—H25B0.9800
C9—C111.392 (3)C25—H25C0.9800
C9—C131.400 (2)S26—O291.4438 (13)
C9—C151.511 (3)S26—O271.4442 (13)
N10—C141.368 (2)S26—O281.4494 (13)
N10—C121.380 (2)S26—C301.825 (2)
N10—C251.484 (2)C30—F311.332 (2)
C11—C121.432 (2)C30—F331.334 (2)
C13—C141.433 (3)C30—F321.343 (2)
C15—O161.348 (2)
C2—C1—C11120.89 (18)C9—C15—O17126.14 (18)
C2—C1—H1119.6C15—O16—C18119.35 (15)
C11—C1—H1119.6C19—C18—C23123.81 (19)
C1—C2—C3119.98 (18)C19—C18—O16120.66 (17)
C1—C2—H2120.0C23—C18—O16115.10 (18)
C3—C2—H2120.0C18—C19—C20116.30 (19)
C4—C3—C2121.5 (2)C18—C19—C24122.96 (18)
C4—C3—H3119.2C20—C19—C24120.74 (19)
C2—C3—H3119.2C21—C20—C19120.8 (2)
C3—C4—C12119.97 (18)C21—C20—H20119.6
C3—C4—H4120.0C19—C20—H20119.6
C12—C4—H4120.0C22—C21—C20121.4 (2)
C6—C5—C14120.10 (19)C22—C21—H21119.3
C6—C5—H5119.9C20—C21—H21119.3
C14—C5—H5119.9C21—C22—C23119.3 (2)
C5—C6—C7122.01 (19)C21—C22—H22120.3
C5—C6—H6119.0C23—C22—H22120.3
C7—C6—H6119.0C22—C23—C18118.3 (2)
C8—C7—C6118.8 (2)C22—C23—H23120.8
C8—C7—H7120.6C18—C23—H23120.8
C6—C7—H7120.6C19—C24—H24A109.5
C7—C8—C13121.51 (19)C19—C24—H24B109.5
C7—C8—H8119.2H24A—C24—H24B109.5
C13—C8—H8119.2C19—C24—H24C109.5
C11—C9—C13121.52 (17)H24A—C24—H24C109.5
C11—C9—C15119.13 (16)H24B—C24—H24C109.5
C13—C9—C15119.27 (18)N10—C25—H25A109.5
C14—N10—C12122.27 (16)N10—C25—H25B109.5
C14—N10—C25118.96 (15)H25A—C25—H25B109.5
C12—N10—C25118.75 (16)N10—C25—H25C109.5
C9—C11—C1122.17 (17)H25A—C25—H25C109.5
C9—C11—C12119.15 (17)H25B—C25—H25C109.5
C1—C11—C12118.68 (18)O29—S26—O27115.28 (8)
N10—C12—C4122.19 (17)O29—S26—O28114.83 (8)
N10—C12—C11118.83 (17)O27—S26—O28114.98 (8)
C4—C12—C11118.94 (17)O29—S26—C30103.24 (9)
C9—C13—C8122.84 (18)O27—S26—C30103.17 (9)
C9—C13—C14117.96 (18)O28—S26—C30102.86 (9)
C8—C13—C14119.11 (17)F31—C30—F33107.69 (17)
N10—C14—C5121.85 (17)F31—C30—F32107.10 (17)
N10—C14—C13119.95 (17)F33—C30—F32106.79 (15)
C5—C14—C13118.17 (19)F31—C30—S26111.75 (13)
O17—C15—O16126.38 (18)F33—C30—S26112.04 (14)
C9—C15—O16107.48 (17)F32—C30—S26111.20 (14)
C11—C1—C2—C30.2 (3)C6—C5—C14—C132.9 (3)
C1—C2—C3—C40.2 (3)C9—C13—C14—N106.8 (3)
C2—C3—C4—C120.6 (3)C8—C13—C14—N10176.55 (17)
C14—C5—C6—C72.0 (3)C9—C13—C14—C5171.09 (17)
C5—C6—C7—C84.3 (3)C8—C13—C14—C55.6 (3)
C6—C7—C8—C131.5 (3)C11—C9—C15—O1795.4 (2)
C13—C9—C11—C1179.90 (18)C13—C9—C15—O1787.7 (2)
C15—C9—C11—C13.1 (3)C11—C9—C15—O1684.6 (2)
C13—C9—C11—C120.5 (3)C13—C9—C15—O1692.3 (2)
C15—C9—C11—C12176.33 (17)O17—C15—O16—C184.5 (3)
C2—C1—C11—C9179.84 (19)C9—C15—O16—C18175.48 (15)
C2—C1—C11—C120.7 (3)C15—O16—C18—C1977.0 (2)
C14—N10—C12—C4178.80 (18)C15—O16—C18—C23110.11 (19)
C25—N10—C12—C40.5 (3)C23—C18—C19—C200.5 (3)
C14—N10—C12—C111.0 (3)O16—C18—C19—C20172.72 (17)
C25—N10—C12—C11177.33 (16)C23—C18—C19—C24178.42 (19)
C3—C4—C12—N10176.74 (17)O16—C18—C19—C246.2 (3)
C3—C4—C12—C111.1 (3)C18—C19—C20—C210.5 (3)
C9—C11—C12—N102.7 (3)C24—C19—C20—C21178.47 (19)
C1—C11—C12—N10176.79 (16)C19—C20—C21—C220.3 (3)
C9—C11—C12—C4179.40 (18)C20—C21—C22—C230.2 (3)
C1—C11—C12—C41.1 (3)C21—C22—C23—C180.2 (3)
C11—C9—C13—C8178.38 (18)C19—C18—C23—C220.4 (3)
C15—C9—C13—C84.8 (3)O16—C18—C23—C22172.97 (17)
C11—C9—C13—C145.1 (3)O29—S26—C30—F3162.96 (16)
C15—C9—C13—C14171.67 (17)O27—S26—C30—F3157.41 (16)
C7—C8—C13—C9173.09 (18)O28—S26—C30—F31177.29 (14)
C7—C8—C13—C143.4 (3)O29—S26—C30—F3357.99 (15)
C12—N10—C14—C5173.96 (17)O27—S26—C30—F33178.36 (13)
C25—N10—C14—C54.3 (3)O28—S26—C30—F3361.75 (15)
C12—N10—C14—C133.8 (3)O29—S26—C30—F32177.41 (13)
C25—N10—C14—C13177.87 (16)O27—S26—C30—F3262.22 (15)
C6—C5—C14—N10179.23 (18)O28—S26—C30—F3257.66 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O27i0.952.503.247 (2)136
C2—H2···O29i0.952.503.435 (2)166
C4—H4···O28ii0.952.393.322 (2)165
C6—H6···O290.952.533.450 (3)163
C7—H7···O280.952.533.253 (3)133
C25—H25C···O28ii0.982.583.423 (3)144
C5—H5···Cg4iii0.953.083.773 (2)132
C6—H6···Cg3iv0.953.363.822 (2)112
C21—H21···Cg3v0.953.383.954 (2)121
C24—H24B···Cg4v0.982.873.649 (2)137
Symmetry codes: (i) x, y+1, z1; (ii) x, y, z1; (iii) x, y1, z; (iv) x, y+1, z+1; (v) x+1, y+2, z+1.
ππ interactions (Å, °) in (I); Cg represents the centroid of the C1–C4/C12/C11 ring (Fig. 1) top
CgICgJCg···CgDihedral angleInterplanar distanceOffset
22vi3.789 (2)0.03.361 (2)1.634 (2)
Notes: Cg···Cg is the distance between ring centroids. The dihedral angle is that between the planes of the rings CgI and CgJ. The interplanar distance is the perpendicular distance of CgI from ring J. The offset is the perpendicular distance of ring I from ring J. Symmetry code: (vi) -x, 2-y, -z.
 

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