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The title compound, C21H24N+·PF6, crystallizes in centrosymmetric hydrogen-bonded clusters consisting of two cations and two anions, via weak aromatic C—H...F inter­actions. The isoquinolinium and dimethyl­phen­yl moieties are not coplanar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015461/lh6431sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015461/lh6431Isup2.hkl
Contains datablock I

CCDC reference: 274589

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.124
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.800 0.970 Tmin' and Tmax expected: 0.960 0.978 RR' = 0.840 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.84 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2-(2,4-Dimethylphenyl)-4-isopropyl-1-methylisoquinolinium hexafluorophosphate top
Crystal data top
C21H24N+·PF6Z = 2
Mr = 435.38F(000) = 452
Triclinic, P1Dx = 1.438 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7413 (4) ÅCell parameters from 9057 reflections
b = 9.0199 (5) Åθ = 1.6–26.0°
c = 12.8984 (5) ŵ = 0.20 mm1
α = 93.027 (3)°T = 150 K
β = 98.039 (3)°Block, colorless
γ = 90.032 (2)°0.2 × 0.14 × 0.11 mm
V = 1005.55 (8) Å3
Data collection top
Nonius KappaCCD
diffractometer
3931 independent reflections
Radiation source: rotating anode2547 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
φ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(MULABS; Blessing, 1995)
h = 1010
Tmin = 0.80, Tmax = 0.97k = 119
9057 measured reflectionsl = 1515
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0614P)2]
where P = (Fo2 + 2Fc2)/3
3931 reflections(Δ/σ)max < 0.001
267 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.39 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.

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
N10.7398 (2)0.19973 (19)0.21239 (12)0.0255 (4)
C10.7161 (2)0.3402 (2)0.24498 (16)0.0250 (5)
C20.7577 (2)0.1596 (2)0.10963 (15)0.0261 (5)
H20.77580.05830.09160.031*
C30.7503 (2)0.2585 (2)0.03376 (15)0.0254 (5)
C40.7184 (2)0.4101 (2)0.06239 (16)0.0254 (5)
C50.7006 (2)0.5211 (2)0.01133 (16)0.0293 (5)
H50.71360.49710.08220.035*
C60.6647 (3)0.6637 (2)0.01877 (17)0.0326 (6)
H60.65340.73760.03150.039*
C70.6447 (3)0.7016 (2)0.12216 (18)0.0345 (6)
H70.61830.80040.14150.041*
C80.6628 (3)0.5972 (2)0.19602 (17)0.0315 (5)
H80.65030.62420.26650.038*
C90.7000 (2)0.4495 (2)0.16788 (15)0.0260 (5)
C100.7091 (3)0.3787 (2)0.35801 (15)0.0311 (5)
H10A0.60330.40620.36730.047*
H10B0.77900.46240.38180.047*
H10C0.74050.29280.39920.047*
C110.7803 (3)0.2110 (2)0.07635 (16)0.0293 (5)
H110.70760.26730.12650.035*
C120.9443 (3)0.2552 (3)0.09061 (18)0.0381 (6)
H12A0.95860.36240.07550.057*
H12B0.96090.23010.16300.057*
H12C1.01860.20170.04240.057*
C130.7511 (3)0.0456 (2)0.10427 (17)0.0403 (6)
H13A0.82990.01240.06290.060*
H13B0.75620.02520.17910.060*
H13C0.64860.01810.08880.060*
C140.7434 (3)0.0770 (2)0.28295 (15)0.0257 (5)
C150.6049 (3)0.0304 (2)0.31146 (15)0.0293 (5)
H150.51140.08000.28860.035*
C160.6052 (3)0.0907 (2)0.37443 (16)0.0298 (5)
C170.7465 (3)0.1574 (2)0.40701 (15)0.0305 (5)
H170.74810.23810.45160.037*
C180.8845 (3)0.1113 (2)0.37740 (16)0.0291 (5)
C190.8822 (3)0.0088 (2)0.31349 (16)0.0286 (5)
H190.97470.04290.29140.034*
C200.4570 (3)0.1500 (3)0.40369 (19)0.0429 (6)
H20A0.38360.06850.40800.064*
H20B0.47790.19460.47180.064*
H20C0.41290.22530.35030.064*
C211.0336 (3)0.1899 (3)0.41287 (19)0.0417 (6)
H21A1.02280.24400.47540.063*
H21B1.11750.11670.42960.063*
H21C1.05730.25990.35670.063*
P10.21525 (7)0.35336 (7)0.29855 (4)0.03268 (19)
F10.10178 (17)0.29938 (18)0.19547 (11)0.0586 (5)
F20.32959 (17)0.40467 (16)0.40121 (10)0.0496 (4)
F30.35977 (15)0.32403 (15)0.23584 (10)0.0429 (4)
F40.2065 (2)0.51925 (16)0.26214 (11)0.0593 (5)
F50.07178 (18)0.37904 (19)0.36042 (12)0.0614 (5)
F60.22752 (18)0.18553 (15)0.33422 (11)0.0504 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0275 (10)0.0249 (10)0.0246 (9)0.0002 (8)0.0043 (8)0.0048 (7)
C10.0207 (12)0.0277 (12)0.0266 (11)0.0016 (9)0.0033 (9)0.0012 (9)
C20.0290 (12)0.0256 (12)0.0238 (11)0.0038 (9)0.0038 (9)0.0003 (9)
C30.0220 (12)0.0282 (12)0.0257 (11)0.0007 (9)0.0014 (9)0.0037 (9)
C40.0216 (11)0.0263 (12)0.0284 (11)0.0025 (9)0.0038 (9)0.0036 (9)
C50.0271 (12)0.0317 (13)0.0290 (12)0.0011 (10)0.0019 (10)0.0075 (9)
C60.0340 (14)0.0253 (13)0.0388 (13)0.0011 (10)0.0044 (11)0.0070 (10)
C70.0328 (13)0.0239 (12)0.0467 (14)0.0004 (10)0.0058 (11)0.0003 (10)
C80.0331 (13)0.0277 (13)0.0332 (12)0.0015 (10)0.0040 (10)0.0021 (10)
C90.0223 (12)0.0264 (12)0.0291 (11)0.0027 (9)0.0024 (9)0.0034 (9)
C100.0315 (13)0.0332 (14)0.0287 (12)0.0018 (10)0.0038 (10)0.0030 (10)
C110.0341 (13)0.0295 (13)0.0247 (11)0.0037 (10)0.0040 (10)0.0051 (9)
C120.0373 (15)0.0450 (15)0.0351 (13)0.0065 (11)0.0129 (11)0.0092 (11)
C130.0547 (17)0.0354 (14)0.0300 (12)0.0042 (12)0.0045 (12)0.0012 (10)
C140.0312 (13)0.0250 (12)0.0212 (11)0.0003 (9)0.0030 (9)0.0056 (9)
C150.0308 (13)0.0321 (13)0.0251 (11)0.0029 (10)0.0045 (10)0.0022 (9)
C160.0367 (13)0.0295 (13)0.0248 (11)0.0025 (10)0.0103 (10)0.0004 (9)
C170.0453 (15)0.0270 (13)0.0194 (11)0.0007 (10)0.0037 (10)0.0042 (9)
C180.0339 (14)0.0291 (13)0.0239 (11)0.0021 (10)0.0025 (10)0.0003 (9)
C190.0306 (13)0.0303 (12)0.0255 (11)0.0010 (10)0.0056 (10)0.0034 (9)
C200.0432 (16)0.0438 (16)0.0447 (14)0.0037 (12)0.0142 (12)0.0068 (12)
C210.0433 (16)0.0406 (15)0.0403 (14)0.0084 (12)0.0000 (12)0.0088 (11)
P10.0306 (4)0.0372 (4)0.0315 (3)0.0011 (3)0.0059 (3)0.0085 (3)
F10.0438 (9)0.0843 (12)0.0436 (9)0.0061 (8)0.0080 (7)0.0030 (8)
F20.0538 (10)0.0583 (10)0.0351 (8)0.0113 (7)0.0009 (7)0.0011 (7)
F30.0377 (8)0.0554 (9)0.0384 (7)0.0074 (7)0.0116 (6)0.0109 (6)
F40.0879 (13)0.0386 (9)0.0565 (9)0.0182 (8)0.0217 (9)0.0195 (7)
F50.0448 (10)0.0859 (13)0.0599 (10)0.0130 (8)0.0268 (8)0.0128 (9)
F60.0670 (11)0.0379 (9)0.0490 (8)0.0037 (7)0.0136 (8)0.0129 (6)
Geometric parameters (Å, º) top
N1—C11.339 (3)C12—H12C0.9800
N1—C21.385 (3)C13—H13A0.9800
N1—C141.467 (2)C13—H13B0.9800
C1—C91.430 (3)C13—H13C0.9800
C1—C101.490 (3)C14—C191.378 (3)
C2—C31.354 (3)C14—C151.385 (3)
C2—H20.9500C15—C161.395 (3)
C3—C41.435 (3)C15—H150.9500
C3—C111.520 (3)C16—C171.394 (3)
C4—C51.411 (3)C16—C201.505 (3)
C4—C91.419 (3)C17—C181.386 (3)
C5—C61.373 (3)C17—H170.9500
C5—H50.9500C18—C191.394 (3)
C6—C71.394 (3)C18—C211.509 (3)
C6—H60.9500C19—H190.9500
C7—C81.368 (3)C20—H20A0.9800
C7—H70.9500C20—H20B0.9800
C8—C91.412 (3)C20—H20C0.9800
C8—H80.9500C21—H21A0.9800
C10—H10A0.9800C21—H21B0.9800
C10—H10B0.9800C21—H21C0.9800
C10—H10C0.9800P1—F51.5887 (16)
C11—C121.526 (3)P1—F41.5906 (15)
C11—C131.529 (3)P1—F21.5910 (14)
C11—H111.0000P1—F11.5972 (14)
C12—H12A0.9800P1—F61.6045 (14)
C12—H12B0.9800P1—F31.6075 (15)
C1—N1—C2122.57 (17)H13A—C13—H13B109.5
C1—N1—C14121.90 (17)C11—C13—H13C109.5
C2—N1—C14115.50 (16)H13A—C13—H13C109.5
N1—C1—C9117.52 (18)H13B—C13—H13C109.5
N1—C1—C10120.27 (18)C19—C14—C15123.03 (19)
C9—C1—C10122.21 (19)C19—C14—N1118.85 (19)
C3—C2—N1122.87 (19)C15—C14—N1118.04 (17)
C3—C2—H2118.6C14—C15—C16118.8 (2)
N1—C2—H2118.6C14—C15—H15120.6
C2—C3—C4117.42 (19)C16—C15—H15120.6
C2—C3—C11120.97 (19)C17—C16—C15118.0 (2)
C4—C3—C11121.58 (18)C17—C16—C20121.2 (2)
C5—C4—C9118.59 (19)C15—C16—C20120.9 (2)
C5—C4—C3122.29 (19)C18—C17—C16123.1 (2)
C9—C4—C3119.09 (18)C18—C17—H17118.5
C6—C5—C4120.3 (2)C16—C17—H17118.5
C6—C5—H5119.8C17—C18—C19118.4 (2)
C4—C5—H5119.8C17—C18—C21120.8 (2)
C5—C6—C7120.9 (2)C19—C18—C21120.8 (2)
C5—C6—H6119.6C14—C19—C18118.8 (2)
C7—C6—H6119.6C14—C19—H19120.6
C8—C7—C6120.4 (2)C18—C19—H19120.6
C8—C7—H7119.8C16—C20—H20A109.5
C6—C7—H7119.8C16—C20—H20B109.5
C7—C8—C9120.3 (2)H20A—C20—H20B109.5
C7—C8—H8119.9C16—C20—H20C109.5
C9—C8—H8119.9H20A—C20—H20C109.5
C8—C9—C4119.53 (18)H20B—C20—H20C109.5
C8—C9—C1120.06 (19)C18—C21—H21A109.5
C4—C9—C1120.40 (19)C18—C21—H21B109.5
C1—C10—H10A109.5H21A—C21—H21B109.5
C1—C10—H10B109.5C18—C21—H21C109.5
H10A—C10—H10B109.5H21A—C21—H21C109.5
C1—C10—H10C109.5H21B—C21—H21C109.5
H10A—C10—H10C109.5F5—P1—F491.42 (9)
H10B—C10—H10C109.5F5—P1—F290.10 (8)
C3—C11—C12109.73 (17)F4—P1—F290.45 (8)
C3—C11—C13113.52 (18)F5—P1—F190.36 (9)
C12—C11—C13110.95 (19)F4—P1—F190.31 (9)
C3—C11—H11107.5F2—P1—F1179.10 (9)
C12—C11—H11107.5F5—P1—F689.83 (9)
C13—C11—H11107.5F4—P1—F6178.74 (9)
C11—C12—H12A109.5F2—P1—F689.39 (8)
C11—C12—H12B109.5F1—P1—F689.83 (8)
H12A—C12—H12B109.5F5—P1—F3178.91 (9)
C11—C12—H12C109.5F4—P1—F389.59 (8)
H12A—C12—H12C109.5F2—P1—F390.31 (8)
H12B—C12—H12C109.5F1—P1—F389.22 (8)
C11—C13—H13A109.5F6—P1—F389.17 (8)
C11—C13—H13B109.5
C2—N1—C1—C93.8 (3)C10—C1—C9—C85.7 (3)
C14—N1—C1—C9174.17 (18)N1—C1—C9—C43.8 (3)
C2—N1—C1—C10175.55 (19)C10—C1—C9—C4175.5 (2)
C14—N1—C1—C106.5 (3)C2—C3—C11—C12100.7 (2)
C1—N1—C2—C31.0 (3)C4—C3—C11—C1277.2 (2)
C14—N1—C2—C3177.05 (19)C2—C3—C11—C1324.1 (3)
N1—C2—C3—C41.7 (3)C4—C3—C11—C13157.99 (19)
N1—C2—C3—C11176.26 (19)C1—N1—C14—C19110.0 (2)
C2—C3—C4—C5176.8 (2)C2—N1—C14—C1972.0 (2)
C11—C3—C4—C55.2 (3)C1—N1—C14—C1573.3 (3)
C2—C3—C4—C91.5 (3)C2—N1—C14—C15104.8 (2)
C11—C3—C4—C9176.47 (19)C19—C14—C15—C160.3 (3)
C9—C4—C5—C60.6 (3)N1—C14—C15—C16176.97 (17)
C3—C4—C5—C6177.7 (2)C14—C15—C16—C171.1 (3)
C4—C5—C6—C70.2 (3)C14—C15—C16—C20177.31 (19)
C5—C6—C7—C81.0 (4)C15—C16—C17—C181.8 (3)
C6—C7—C8—C90.8 (3)C20—C16—C17—C18176.56 (19)
C7—C8—C9—C40.0 (3)C16—C17—C18—C191.1 (3)
C7—C8—C9—C1178.9 (2)C16—C17—C18—C21178.5 (2)
C5—C4—C9—C80.8 (3)C15—C14—C19—C181.0 (3)
C3—C4—C9—C8177.61 (19)N1—C14—C19—C18177.66 (18)
C5—C4—C9—C1179.61 (18)C17—C18—C19—C140.3 (3)
C3—C4—C9—C11.3 (3)C21—C18—C19—C14180.0 (2)
N1—C1—C9—C8175.01 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F4i0.952.513.445 (2)167
C19—H19···F6ii0.952.533.384 (3)149
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
 

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