Literature DB >> 21587794

9-Benzyl-10-methyl-acridinium trifluoro-methane-sulfonate.

Damian Trzybiński1, Beata Zadykowicz, Karol Krzymiński, Artur Sikorski, Jerzy Błażejowski.   

Abstract

In the crystal structure of the title compound, C(21)H(18)N(+)·CF(3)OS(3) (-), the cations form inversion dimers through π-π inter-actions between the acridine ring systems. These dimers are further linked by C-H⋯π inter-actions. The cations and anions are connected by C-H⋯O, C-F⋯π and S-O⋯π inter-actions. The acridine and benzene ring systems are oriented at a dihedral angle of 76.8 (1)°with respect to each other. The acridine moieties are either parallel or inclined at an angle of 62.4 (1)° in the crystal structure.

Entities:  

Year:  2010        PMID： 21587794      PMCID： PMC3006932          DOI： 10.1107/S160053681001963X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to acridinium derivatives, see: King et al. (2007 ▶); Roda et al. (2003 ▶); Wróblewska et al. (2004 ▶); Trzybiński et al. (2010 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2007 ▶); Trzybiński et al. (2010 ▶). For inter­molecular inter­actions, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Huntress & Shaw (1948 ▶); Sikorski et al. (2007 ▶); Trzybiński et al. (2010 ▶).

Experimental

Crystal data

C21H18N+·CF3O3S− M = 433.44 Monoclinic, a = 14.6211 (7) Å b = 8.2514 (2) Å c = 17.2900 (8) Å β = 107.707 (5)° V = 1987.12 (15) Å3 Z = 4 Mo Kα radiation μ = 0.22 mm−1 T = 295 K 0.41 × 0.25 × 0.08 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.953, T max = 0.988 16520 measured reflections 3528 independent reflections 2191 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.153 S = 1.06 3528 reflections 272 parameters H-atom parameters constrained Δρmax = 0.37 e Å−3 Δρmin = −0.28 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001963X/om2343sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681001963X/om2343Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H18N+·CF3O3S−F(000) = 896
Mr = 433.44Dx = 1.449 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5587 reflections
a = 14.6211 (7) Åθ = 3.2–29.2°
b = 8.2514 (2) ŵ = 0.22 mm−1
c = 17.2900 (8) ÅT = 295 K
β = 107.707 (5)°Plate, light-orange
V = 1987.12 (15) Å30.41 × 0.25 × 0.08 mm
Z = 4
Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer3528 independent reflections
Radiation source: Enhanced (Mo) X-ray Source2191 reflections with I > 2σ(I)
graphiteRint = 0.048
Detector resolution: 10.4002 pixels mm-1θmax = 25.1°, θmin = 3.3°
ω scansh = −17→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −9→9
Tmin = 0.953, Tmax = 0.988l = −20→20
16520 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0814P)2 + 0.218P] where P = (Fo2 + 2Fc2)/3
3528 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
xyzUiso*/Ueq
C11.0142 (2)0.2164 (4)0.5705 (2)0.0680 (10)
H11.03410.18380.62450.082*
C21.0692 (3)0.1812 (4)0.5215 (3)0.0870 (13)
H21.12670.12510.54190.104*
C31.0384 (4)0.2302 (5)0.4410 (3)0.0919 (14)
H31.07600.20370.40810.110*
C40.9568 (3)0.3141 (4)0.4080 (3)0.0793 (11)
H40.93950.34510.35380.095*
C50.6717 (3)0.5685 (3)0.4389 (2)0.0616 (9)
H50.65660.61030.38660.074*
C60.6130 (3)0.5955 (4)0.4840 (3)0.0703 (10)
H60.55720.65540.46200.084*
C70.6331 (2)0.5369 (4)0.5617 (2)0.0641 (9)
H70.59030.55510.59110.077*
C80.7146 (2)0.4531 (3)0.59546 (18)0.0515 (8)
H80.72750.41550.64840.062*
C90.8675 (2)0.3374 (3)0.58718 (16)0.0416 (7)
N100.8163 (2)0.4426 (3)0.42625 (14)0.0545 (7)
C110.9266 (2)0.3027 (3)0.53895 (18)0.0490 (8)
C120.8982 (2)0.3545 (3)0.45600 (19)0.0536 (8)
C130.7815 (2)0.4203 (3)0.55233 (15)0.0411 (7)
C140.7575 (2)0.4760 (3)0.47112 (18)0.0486 (8)
C150.8974 (2)0.2879 (3)0.67532 (17)0.0514 (8)
H15A0.86410.35590.70390.062*
H15B0.96570.30760.69870.062*
C160.8769 (2)0.1104 (3)0.68912 (16)0.0450 (7)
C170.7896 (2)0.0396 (3)0.64921 (19)0.0565 (8)
H170.74310.09910.61110.068*
C180.7708 (2)−0.1185 (4)0.6653 (2)0.0623 (9)
H180.7117−0.16450.63830.075*
C190.8388 (3)−0.2080 (4)0.72059 (19)0.0661 (10)
H190.8256−0.31410.73200.079*
C200.9259 (3)−0.1408 (4)0.7590 (2)0.0739 (11)
H200.9730−0.20220.79540.089*
C210.9445 (3)0.0179 (4)0.74392 (18)0.0627 (9)
H211.00380.06310.77130.075*
C220.7881 (3)0.4991 (6)0.3401 (2)0.0921 (13)
H22A0.77890.61440.33830.138*
H22B0.72940.44700.30980.138*
H22C0.83790.47210.31670.138*
S230.84575 (6)0.55745 (8)0.14455 (5)0.0509 (3)
O240.8608 (2)0.4008 (3)0.17948 (15)0.0869 (8)
O250.87049 (18)0.6881 (3)0.20097 (14)0.0771 (7)
O260.75711 (18)0.5802 (3)0.08205 (16)0.0925 (8)
C270.9326 (2)0.5715 (3)0.09040 (19)0.0553 (8)
F281.01928 (18)0.5412 (4)0.13525 (16)0.1322 (11)
F290.9156 (2)0.4660 (3)0.03015 (15)0.1090 (9)
F300.9335 (2)0.7119 (3)0.05685 (18)0.1184 (9)
U11U22U33U12U13U23
C10.051 (2)0.0523 (17)0.102 (3)−0.0032 (16)0.025 (2)−0.0051 (18)
C20.062 (3)0.061 (2)0.147 (4)−0.0002 (18)0.045 (3)−0.014 (3)
C30.098 (4)0.074 (3)0.133 (4)−0.020 (2)0.078 (3)−0.035 (3)
C40.094 (3)0.070 (2)0.092 (3)−0.021 (2)0.055 (3)−0.021 (2)
C50.063 (2)0.0494 (17)0.058 (2)−0.0072 (16)−0.0032 (18)0.0132 (15)
C60.058 (2)0.0511 (18)0.092 (3)0.0070 (16)0.007 (2)−0.0005 (19)
C70.055 (2)0.0556 (18)0.082 (3)0.0044 (16)0.0208 (19)−0.0152 (18)
C80.057 (2)0.0479 (16)0.0494 (17)−0.0042 (15)0.0155 (16)−0.0066 (13)
C90.0406 (17)0.0361 (14)0.0437 (16)−0.0092 (12)0.0063 (14)−0.0046 (12)
N100.0601 (18)0.0573 (14)0.0459 (14)−0.0176 (13)0.0158 (13)0.0010 (12)
C110.0440 (18)0.0397 (14)0.065 (2)−0.0079 (13)0.0191 (16)−0.0050 (14)
C120.061 (2)0.0460 (16)0.064 (2)−0.0236 (15)0.0350 (18)−0.0155 (15)
C130.0463 (17)0.0345 (13)0.0397 (15)−0.0065 (12)0.0091 (13)−0.0031 (12)
C140.054 (2)0.0409 (15)0.0485 (18)−0.0132 (13)0.0121 (16)0.0005 (13)
C150.0536 (19)0.0475 (16)0.0480 (17)−0.0013 (13)0.0078 (15)0.0024 (13)
C160.0483 (18)0.0450 (15)0.0387 (15)−0.0019 (13)0.0088 (14)−0.0037 (12)
C170.0489 (19)0.0520 (17)0.0626 (19)−0.0003 (14)0.0081 (16)−0.0030 (15)
C180.061 (2)0.0570 (19)0.069 (2)−0.0097 (16)0.0209 (18)−0.0068 (17)
C190.101 (3)0.0482 (17)0.055 (2)−0.0102 (19)0.032 (2)−0.0009 (16)
C200.095 (3)0.058 (2)0.053 (2)0.004 (2)−0.0001 (19)0.0128 (16)
C210.068 (2)0.0598 (19)0.0486 (18)−0.0066 (16)0.0000 (17)0.0059 (15)
C220.095 (3)0.134 (3)0.046 (2)−0.025 (3)0.020 (2)0.017 (2)
S230.0509 (5)0.0466 (4)0.0560 (5)−0.0018 (3)0.0174 (4)−0.0017 (3)
O240.131 (2)0.0614 (14)0.0900 (17)0.0137 (14)0.0658 (17)0.0192 (13)
O250.0813 (18)0.0706 (14)0.0855 (16)−0.0086 (12)0.0343 (14)−0.0294 (13)
O260.0492 (15)0.114 (2)0.1010 (19)−0.0060 (14)0.0025 (14)−0.0007 (16)
C270.058 (2)0.0492 (17)0.060 (2)0.0005 (15)0.0213 (17)0.0023 (15)
F280.0559 (15)0.234 (3)0.1091 (19)0.0300 (17)0.0292 (14)0.015 (2)
F290.159 (3)0.0953 (15)0.1012 (17)−0.0266 (15)0.0826 (17)−0.0321 (13)
F300.156 (2)0.0668 (13)0.172 (2)0.0008 (14)0.108 (2)0.0329 (14)
C1—C21.364 (5)C13—C141.416 (4)
C1—C111.421 (4)C15—C161.528 (4)
C1—H10.9300C15—H15A0.9700
C2—C31.387 (6)C15—H15B0.9700
C2—H20.9300C16—C211.374 (4)
C3—C41.346 (6)C16—C171.382 (4)
C3—H30.9300C17—C181.378 (4)
C4—C121.403 (5)C17—H170.9300
C4—H40.9300C18—C191.367 (4)
C5—C61.342 (5)C18—H180.9300
C5—C141.428 (4)C19—C201.363 (5)
C5—H50.9300C19—H190.9300
C6—C71.372 (5)C20—C211.378 (4)
C6—H60.9300C20—H200.9300
C7—C81.348 (4)C21—H210.9300
C7—H70.9300C22—H22A0.9600
C8—C131.425 (4)C22—H22B0.9600
C8—H80.9300C22—H22C0.9600
C9—C131.396 (4)S23—O241.415 (2)
C9—C111.402 (4)S23—O251.425 (2)
C9—C151.508 (4)S23—O261.425 (2)
N10—C141.350 (4)S23—C271.796 (3)
N10—C121.361 (4)C27—F281.293 (4)
N10—C221.495 (4)C27—F301.297 (3)
C11—C121.432 (4)C27—F291.322 (3)
C2—C1—C11120.1 (4)C9—C15—C16114.0 (2)
C2—C1—H1120.0C9—C15—H15A108.8
C11—C1—H1120.0C16—C15—H15A108.8
C1—C2—C3119.2 (4)C9—C15—H15B108.8
C1—C2—H2120.4C16—C15—H15B108.8
C3—C2—H2120.4H15A—C15—H15B107.7
C4—C3—C2123.4 (4)C21—C16—C17118.1 (3)
C4—C3—H3118.3C21—C16—C15120.4 (3)
C2—C3—H3118.3C17—C16—C15121.5 (2)
C3—C4—C12119.6 (4)C18—C17—C16120.6 (3)
C3—C4—H4120.2C18—C17—H17119.7
C12—C4—H4120.2C16—C17—H17119.7
C6—C5—C14120.2 (3)C19—C18—C17120.4 (3)
C6—C5—H5119.9C19—C18—H18119.8
C14—C5—H5119.9C17—C18—H18119.8
C5—C6—C7121.7 (3)C20—C19—C18119.6 (3)
C5—C6—H6119.2C20—C19—H19120.2
C7—C6—H6119.2C18—C19—H19120.2
C8—C7—C6120.2 (4)C19—C20—C21120.3 (3)
C8—C7—H7119.9C19—C20—H20119.9
C6—C7—H7119.9C21—C20—H20119.9
C7—C8—C13121.9 (3)C16—C21—C20121.1 (3)
C7—C8—H8119.1C16—C21—H21119.5
C13—C8—H8119.1C20—C21—H21119.5
C13—C9—C11118.7 (3)N10—C22—H22A109.5
C13—C9—C15121.0 (3)N10—C22—H22B109.5
C11—C9—C15120.2 (3)H22A—C22—H22B109.5
C14—N10—C12122.2 (3)N10—C22—H22C109.5
C14—N10—C22118.6 (3)H22A—C22—H22C109.5
C12—N10—C22119.2 (3)H22B—C22—H22C109.5
C9—C11—C1121.4 (3)O24—S23—O25115.13 (15)
C9—C11—C12119.4 (3)O24—S23—O26115.57 (17)
C1—C11—C12119.2 (3)O25—S23—O26113.74 (15)
N10—C12—C4122.0 (3)O24—S23—C27103.79 (14)
N10—C12—C11119.5 (3)O25—S23—C27103.62 (15)
C4—C12—C11118.5 (3)O26—S23—C27102.73 (16)
C9—C13—C14120.4 (3)F28—C27—F30107.4 (3)
C9—C13—C8122.6 (2)F28—C27—F29105.1 (3)
C14—C13—C8117.0 (3)F30—C27—F29105.1 (3)
N10—C14—C13119.6 (3)F28—C27—S23113.2 (2)
N10—C14—C5121.5 (3)F30—C27—S23113.3 (2)
C13—C14—C5118.9 (3)F29—C27—S23112.0 (2)
C11—C1—C2—C3−0.2 (5)C12—N10—C14—C5−179.9 (2)
C1—C2—C3—C41.2 (6)C22—N10—C14—C5−2.4 (4)
C2—C3—C4—C12−0.6 (6)C9—C13—C14—N102.8 (4)
C14—C5—C6—C70.4 (5)C8—C13—C14—N10−177.3 (2)
C5—C6—C7—C81.6 (5)C9—C13—C14—C5−176.4 (2)
C6—C7—C8—C13−0.9 (4)C8—C13—C14—C53.5 (4)
C13—C9—C11—C1−179.0 (2)C6—C5—C14—N10177.8 (3)
C15—C9—C11—C12.0 (4)C6—C5—C14—C13−3.0 (4)
C13—C9—C11—C120.7 (4)C13—C9—C15—C1699.8 (3)
C15—C9—C11—C12−178.3 (2)C11—C9—C15—C16−81.1 (3)
C2—C1—C11—C9178.5 (3)C9—C15—C16—C21136.1 (3)
C2—C1—C11—C12−1.2 (4)C9—C15—C16—C17−45.8 (4)
C14—N10—C12—C4177.2 (3)C21—C16—C17—C181.1 (5)
C22—N10—C12—C4−0.4 (4)C15—C16—C17—C18−177.0 (3)
C14—N10—C12—C11−3.7 (4)C16—C17—C18—C19−0.5 (5)
C22—N10—C12—C11178.8 (3)C17—C18—C19—C20−1.0 (5)
C3—C4—C12—N10178.3 (3)C18—C19—C20—C211.9 (5)
C3—C4—C12—C11−0.9 (5)C17—C16—C21—C20−0.2 (5)
C9—C11—C12—N102.8 (4)C15—C16—C21—C20177.9 (3)
C1—C11—C12—N10−177.5 (2)C19—C20—C21—C16−1.3 (5)
C9—C11—C12—C4−178.0 (3)O24—S23—C27—F28−54.1 (3)
C1—C11—C12—C41.7 (4)O25—S23—C27—F2866.5 (3)
C11—C9—C13—C14−3.5 (4)O26—S23—C27—F28−174.8 (3)
C15—C9—C13—C14175.5 (2)O24—S23—C27—F30−176.8 (3)
C11—C9—C13—C8176.6 (2)O25—S23—C27—F30−56.1 (3)
C15—C9—C13—C8−4.4 (4)O26—S23—C27—F3062.5 (3)
C7—C8—C13—C9178.3 (2)O24—S23—C27—F2964.6 (3)
C7—C8—C13—C14−1.7 (4)O25—S23—C27—F29−174.8 (2)
C12—N10—C14—C130.9 (4)O26—S23—C27—F29−56.2 (2)
C22—N10—C14—C13178.5 (3)
Cg4 is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O26i0.932.493.398 (5)167
C3—H3···Cg4ii0.932.743.630 (5)161
C15—H15B···O25iii0.972.493.423 (4)160
C22—H22B···O25iv0.962.563.386 (5)144
C22—H22C···O240.962.563.361 (5)141
XIJI···JX···JX–I···J
C27F30Cg3v3.115 (3)4.233 (3)143.0 (2)
S23O26Cg1v3.085 (3)4.167 (2)131.4 (2)
IJCgI···CgJDihedral angleCgI_PerpCgI_Offset
12iii3.806 (2)2.11 (15)3.575 (2)1.306 (2)
21iii3.806 (2)2.11 (15)3.530 (2)1.423 (2)
22iii3.886 (2)0.02 (15)3.563 (2)1.551 (2)
Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C16–C21 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯O26i0.932.493.398 (5)167
C3—H3⋯Cg4ii0.932.743.630 (5)161
C15—H15B⋯O25iii0.972.493.423 (4)160
C22—H22B⋯O25iv0.962.563.386 (5)144
C22—H22C⋯O240.962.563.361 (5)141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Table 2

C–F⋯π and S–O⋯π inter­actions (Å,°)

Cg1 and Cg3 are the centroids of the C9/N10/C11–C14 and C5–C8/C13/C14 rings, respectively.

XIJI⋯JX⋯JX–I⋯J
C27F30Cg3v3.115 (3)4.233 (3)143.0 (2)
S23O26Cg1v3.085 (3)4.167 (2)131.4 (2)

Symmetry code: (v) –x + , y + , –z + .

Table 3

π–π inter­actions (Å, °)

Cg1 and Cg2 are the centroids of the C9/N10/C11–C14 and C1–C4/C11/C12 rings, respectively. CgI⋯CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI_Perp is the perpendicular distance of CgI from ring J. CgI_Offset is the distance between CgI and perpendicular projection of CgJ on ring I.

IJCgI⋯CgJDihedral angleCgI_PerpCgI_Offset
12iii3.806 (2)2.11 (15)3.575 (2)1.306 (2)
21iii3.806 (2)2.11 (15)3.530 (2)1.423 (2)
22iii3.886 (2)0.02 (15)3.563 (2)1.551 (2)

Symmetry code: (iii) –x + 2, –y + 1, –z + 1.

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2.  Flow injection analysis of H2O2 in natural waters using acridinium ester chemiluminescence: method development and optimization using a kinetic model.

Authors:  D Whitney King; William J Cooper; Steven A Rusak; Barrie M Peake; James J Kiddle; Daniel W O'Sullivan; Megan L Melamed; Chris R Morgan; Stephen M Theberge
Journal:  Anal Chem       Date:  2007-04-25       Impact factor: 6.986

3.  4-Benzyl-2,6-dimethylpyridine, 1-benzylisoquinoline, 9-benzylacridine, and certain relatives.

Authors:  E H HUNTRESS; E N SHAW
Journal:  J Org Chem       Date:  1948-09       Impact factor: 4.354

4.  Experimental electron density study of the supramolecular aggregation between 4,4'-dipyridyl-N,N'-dioxide and 1,4-diiodotetrafluorobenzene at 90 K.

Authors:  Riccardo Bianchi; Alessandra Forni; Tullio Pilati
Journal:  Acta Crystallogr B       Date:  2004-09-15

5.  Origin of chemiluminescence accompanying the reaction of the 9-cyano-10-methylacridinium cation with hydrogen peroxide.

Authors:  A Wróblewska; O M Huta; S V Midyanyj; I O Patsay; J Rak; J Błazejowski
Journal:  J Org Chem       Date:  2004-03-05       Impact factor: 4.354

6.  9-(2-Ethyl-phenoxy-carbon-yl)-10-methyl-acridinium trifluoro-methane-sulfonate.

Authors:  Damian Trzybiński; Karol Krzymiński; Artur Sikorski; Piotr Malecha; Jerzy Błażejowski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-13

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  7 in total
  1 in total

1.  9-Phenyl-10H-acridinium trifluoro-methane-sulfonate.

Authors:  Damian Trzybiński; Beata Zadykowicz; Karol Krzymiński; Artur Sikorski; Jerzy Błażejowski
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-20
  1 in total

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