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The title compound, C19H23N2+·ClO4-, also known as LDS 698, contains almost parallel pyridyl and phenyl ring systems and an in-plane di­methyl­amino group. The extended pyridyl amino­ethyl group is nearly perpendicular to the dimethyl­amino group. The mol­ecules stack along the a axis, with the ring systems oblique to this axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802019013/om6113sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802019013/om6113Isup2.hkl
Contains datablock I

CCDC reference: 200780

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.046
  • wR factor = 0.159
  • Data-to-parameter ratio = 15.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 44.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1998); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.

2-{4-[4-(Dimethylamino)phenyl]-1,3-butadienyl}-1-ethylpyridinium perchlorate top
Crystal data top
C19H23N2+·ClO4Z = 2
Mr = 378.84F(000) = 400
Triclinic, P1Dx = 1.349 Mg m3
a = 7.8213 (14) ÅMo Kα radiation, λ = 0.71069 Å
b = 11.1055 (13) ÅCell parameters from 20 reflections
c = 11.494 (2) Åθ = 6.1–9.4°
α = 90.003 (18)°µ = 0.23 mm1
β = 106.098 (15)°T = 296 K
γ = 102.960 (14)°Prism, dark purple
V = 932.8 (3) Å30.50 × 0.50 × 0.20 mm
Data collection top
Rigaku AFC-6S
diffractometer
1835 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
2θ/ω scansh = 109
Absorption correction: ψ scan
(North et al., 1968)
k = 014
Tmin = 0.893, Tmax = 0.955l = 1414
4516 measured reflections3 standard reflections every 150 reflections
4297 independent reflections intensity decay: 0.5%
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0668P)2 + 0.0636P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.004
4297 reflectionsΔρmax = 0.23 e Å3
277 parametersΔρmin = 0.23 e Å3
20 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.030 (4)
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*/UeqOcc. (<1)
Cl10.73521 (11)0.69972 (7)0.26333 (6)0.0548 (3)
O10.735 (2)0.6051 (6)0.1800 (8)0.100 (5)0.57 (5)
O20.6076 (14)0.6526 (12)0.3291 (10)0.084 (4)0.57 (5)
O30.9133 (7)0.740 (2)0.3456 (8)0.093 (4)0.57 (5)
O40.684 (3)0.8014 (11)0.1986 (9)0.083 (3)0.57 (5)
O1A0.5954 (14)0.6724 (19)0.3230 (11)0.092 (5)0.43 (5)
O2A0.9080 (11)0.705 (2)0.3488 (9)0.078 (4)0.43 (5)
O3A0.701 (3)0.6057 (7)0.1702 (8)0.060 (4)0.43 (5)
O4A0.736 (4)0.8161 (7)0.2113 (11)0.107 (6)0.43 (5)
N10.5277 (3)0.2720 (2)0.3203 (2)0.0448 (6)
N191.1781 (4)0.3155 (2)1.0413 (2)0.0574 (7)
C20.5792 (4)0.1624 (2)0.3257 (2)0.0395 (7)
C30.5465 (4)0.0963 (3)0.2151 (3)0.0485 (7)
H3A0.57800.02040.21500.058*
C40.4695 (4)0.1408 (3)0.1071 (3)0.0570 (9)
H4A0.44860.09530.03460.068*
C50.4230 (4)0.2534 (3)0.1063 (3)0.0582 (9)
H5A0.37100.28480.03340.070*
C60.4540 (4)0.3173 (3)0.2128 (3)0.0554 (8)
H6A0.42440.39390.21270.066*
C70.5522 (4)0.3495 (3)0.4330 (3)0.0580 (9)
H7A0.51320.29650.49240.070*
H7B0.47480.40810.41380.070*
C80.7467 (5)0.4189 (3)0.4869 (3)0.0739 (11)
H8A0.75710.46430.56060.111*
H8B0.78340.47550.43040.111*
H8C0.82430.36150.50420.111*
C90.6598 (4)0.1188 (3)0.4412 (2)0.0454 (7)
H9A0.66580.16600.50970.055*
C100.7268 (4)0.0184 (3)0.4606 (3)0.0433 (7)
H10A0.72200.03020.39340.052*
C110.8051 (4)0.0194 (3)0.5775 (3)0.0444 (7)
H11A0.81200.03000.64470.053*
C120.8694 (4)0.1215 (3)0.5967 (2)0.0430 (7)
H12A0.86060.16900.52770.052*
C130.9512 (4)0.1674 (2)0.7118 (2)0.0387 (6)
C140.9943 (4)0.2833 (2)0.7153 (3)0.0421 (7)
H14A0.97140.32870.64240.051*
C151.0688 (4)0.3329 (3)0.8216 (3)0.0446 (7)
H15A1.09540.41020.81910.053*
C161.1054 (4)0.2678 (3)0.9341 (3)0.0416 (7)
C171.0645 (4)0.1507 (3)0.9312 (3)0.0470 (7)
H17A1.08750.10481.00380.056*
C180.9915 (4)0.1027 (3)0.8237 (3)0.0459 (7)
H18A0.96810.02430.82560.055*
C201.2431 (4)0.4280 (3)1.0443 (3)0.0618 (9)
H20A1.34130.41611.00740.093*
H20B1.14490.49461.00050.093*
H20C1.28640.44781.12700.093*
C211.2025 (5)0.2510 (4)1.1565 (3)0.0750 (11)
H21A1.08880.23331.15860.113*
H21B1.29370.17491.16570.113*
H21C1.24130.30211.22140.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0621 (5)0.0580 (5)0.0418 (4)0.0116 (4)0.0127 (4)0.0029 (4)
O10.098 (7)0.086 (7)0.106 (8)0.025 (5)0.009 (5)0.052 (6)
O20.090 (8)0.093 (6)0.084 (7)0.022 (5)0.048 (6)0.037 (5)
O30.063 (5)0.120 (8)0.078 (6)0.004 (3)0.003 (4)0.038 (5)
O40.117 (7)0.051 (4)0.088 (5)0.023 (4)0.036 (4)0.013 (4)
O1A0.057 (8)0.181 (15)0.052 (7)0.045 (8)0.024 (6)0.010 (8)
O2A0.060 (6)0.099 (9)0.058 (6)0.011 (4)0.006 (5)0.002 (5)
O3A0.073 (6)0.062 (7)0.045 (6)0.022 (4)0.013 (4)0.008 (5)
O4A0.132 (11)0.065 (7)0.105 (9)0.013 (6)0.011 (7)0.028 (6)
N10.0428 (14)0.0454 (15)0.0472 (14)0.0103 (11)0.0143 (11)0.0081 (12)
N190.0671 (18)0.0583 (17)0.0493 (15)0.0262 (14)0.0111 (13)0.0117 (13)
C20.0397 (16)0.0366 (16)0.0445 (16)0.0058 (13)0.0179 (13)0.0071 (13)
C30.0554 (19)0.0420 (16)0.0492 (18)0.0095 (14)0.0182 (15)0.0018 (14)
C40.055 (2)0.071 (2)0.0389 (16)0.0043 (17)0.0124 (15)0.0011 (16)
C50.054 (2)0.069 (2)0.0484 (19)0.0099 (18)0.0125 (16)0.0226 (18)
C60.0531 (19)0.056 (2)0.058 (2)0.0178 (16)0.0129 (16)0.0191 (17)
C70.066 (2)0.053 (2)0.060 (2)0.0255 (17)0.0170 (17)0.0041 (16)
C80.079 (3)0.053 (2)0.082 (3)0.0128 (19)0.012 (2)0.0070 (19)
C90.0582 (19)0.0421 (17)0.0365 (15)0.0123 (14)0.0140 (13)0.0065 (13)
C100.0429 (16)0.0450 (17)0.0432 (16)0.0075 (14)0.0164 (13)0.0090 (14)
C110.0452 (17)0.0436 (17)0.0441 (16)0.0073 (14)0.0147 (13)0.0059 (14)
C120.0422 (16)0.0457 (17)0.0412 (15)0.0077 (14)0.0137 (13)0.0030 (13)
C130.0375 (15)0.0380 (16)0.0420 (15)0.0072 (13)0.0149 (13)0.0033 (13)
C140.0462 (17)0.0384 (16)0.0415 (15)0.0079 (13)0.0139 (13)0.0023 (13)
C150.0481 (17)0.0327 (15)0.0563 (18)0.0116 (13)0.0186 (14)0.0027 (14)
C160.0406 (16)0.0396 (16)0.0456 (16)0.0093 (13)0.0141 (13)0.0090 (13)
C170.0553 (19)0.0475 (18)0.0409 (16)0.0158 (15)0.0151 (14)0.0008 (14)
C180.0547 (18)0.0392 (16)0.0498 (17)0.0193 (14)0.0180 (15)0.0055 (14)
C200.057 (2)0.056 (2)0.069 (2)0.0198 (17)0.0078 (17)0.0213 (18)
C210.092 (3)0.094 (3)0.0460 (19)0.037 (2)0.0168 (19)0.0131 (19)
Geometric parameters (Å, º) top
Cl1—O11.423 (2)C8—H8B0.9600
Cl1—O2A1.423 (2)C8—H8C0.9600
Cl1—O31.423 (2)C9—C101.329 (4)
Cl1—O3A1.423 (2)C9—H9A0.9300
Cl1—O1A1.423 (2)C10—C111.419 (4)
Cl1—O21.423 (2)C10—H10A0.9300
Cl1—O4A1.423 (2)C11—C121.336 (4)
Cl1—O41.424 (2)C11—H11A0.9300
N1—C61.359 (4)C12—C131.448 (4)
N1—C21.361 (3)C12—H12A0.9300
N1—C71.498 (4)C13—C181.394 (4)
N19—C161.367 (4)C13—C141.400 (4)
N19—C201.447 (4)C14—C151.372 (4)
N19—C211.449 (4)C14—H14A0.9300
C2—C31.399 (4)C15—C161.407 (4)
C2—C91.438 (4)C15—H15A0.9300
C3—C41.366 (4)C16—C171.405 (4)
C3—H3A0.9300C17—C181.373 (4)
C4—C51.377 (4)C17—H17A0.9300
C4—H4A0.9300C18—H18A0.9300
C5—C61.349 (4)C20—H20A0.9600
C5—H5A0.9300C20—H20B0.9600
C6—H6A0.9300C20—H20C0.9600
C7—C81.498 (4)C21—H21A0.9600
C7—H7A0.9700C21—H21B0.9600
C7—H7B0.9700C21—H21C0.9600
C8—H8A0.9600
O1—Cl1—O3109.51 (9)H8B—C8—H8C109.5
O2A—Cl1—O3A109.51 (9)C10—C9—C2127.0 (3)
O2A—Cl1—O1A109.49 (9)C10—C9—H9A116.5
O3A—Cl1—O1A109.49 (9)C2—C9—H9A116.5
O1—Cl1—O2109.50 (9)C9—C10—C11124.1 (3)
O3—Cl1—O2109.48 (9)C9—C10—H10A117.9
O2A—Cl1—O4A109.49 (9)C11—C10—H10A117.9
O3A—Cl1—O4A109.44 (9)C12—C11—C10124.0 (3)
O1A—Cl1—O4A109.42 (9)C12—C11—H11A118.0
O1—Cl1—O4109.46 (9)C10—C11—H11A118.0
O3—Cl1—O4109.48 (9)C11—C12—C13127.9 (3)
O2—Cl1—O4109.40 (9)C11—C12—H12A116.0
C6—N1—C2121.8 (3)C13—C12—H12A116.0
C6—N1—C7116.7 (3)C18—C13—C14116.0 (3)
C2—N1—C7121.5 (2)C18—C13—C12123.9 (3)
C16—N19—C20121.5 (3)C14—C13—C12120.1 (3)
C16—N19—C21120.9 (3)C15—C14—C13122.9 (3)
C20—N19—C21117.5 (3)C15—C14—H14A118.6
N1—C2—C3116.7 (2)C13—C14—H14A118.6
N1—C2—C9120.1 (3)C14—C15—C16120.6 (3)
C3—C2—C9123.2 (3)C14—C15—H15A119.7
C4—C3—C2121.5 (3)C16—C15—H15A119.7
C4—C3—H3A119.3N19—C16—C17121.4 (3)
C2—C3—H3A119.3N19—C16—C15121.8 (3)
C3—C4—C5119.7 (3)C17—C16—C15116.8 (3)
C3—C4—H4A120.2C18—C17—C16121.5 (3)
C5—C4—H4A120.2C18—C17—H17A119.3
C6—C5—C4119.0 (3)C16—C17—H17A119.3
C6—C5—H5A120.5C17—C18—C13122.2 (3)
C4—C5—H5A120.5C17—C18—H18A118.9
C5—C6—N1121.3 (3)C13—C18—H18A118.9
C5—C6—H6A119.4N19—C20—H20A109.5
N1—C6—H6A119.4N19—C20—H20B109.5
N1—C7—C8112.3 (3)H20A—C20—H20B109.5
N1—C7—H7A109.1N19—C20—H20C109.5
C8—C7—H7A109.1H20A—C20—H20C109.5
N1—C7—H7B109.1H20B—C20—H20C109.5
C8—C7—H7B109.1N19—C21—H21A109.5
H7A—C7—H7B107.9N19—C21—H21B109.5
C7—C8—H8A109.5H21A—C21—H21B109.5
C7—C8—H8B109.5N19—C21—H21C109.5
H8A—C8—H8B109.5H21A—C21—H21C109.5
C7—C8—H8C109.5H21B—C21—H21C109.5
H8A—C8—H8C109.5
C6—N1—C2—C32.2 (4)C10—C11—C12—C13180.0 (3)
C7—N1—C2—C3178.7 (3)C11—C12—C13—C186.4 (5)
C6—N1—C2—C9178.8 (3)C11—C12—C13—C14173.4 (3)
C7—N1—C2—C90.3 (4)C18—C13—C14—C151.1 (4)
N1—C2—C3—C41.0 (4)C12—C13—C14—C15178.8 (2)
C9—C2—C3—C4180.0 (3)C13—C14—C15—C160.2 (4)
C2—C3—C4—C50.2 (5)C20—N19—C16—C17171.5 (3)
C3—C4—C5—C60.3 (5)C21—N19—C16—C174.8 (4)
C4—C5—C6—N10.9 (5)C20—N19—C16—C158.1 (4)
C2—N1—C6—C52.2 (4)C21—N19—C16—C15175.6 (3)
C7—N1—C6—C5178.6 (3)C14—C15—C16—N19179.4 (3)
C6—N1—C7—C8102.3 (3)C14—C15—C16—C170.9 (4)
C2—N1—C7—C876.9 (3)N19—C16—C17—C18180.0 (3)
N1—C2—C9—C10175.5 (3)C15—C16—C17—C180.4 (4)
C3—C2—C9—C105.5 (5)C16—C17—C18—C131.0 (5)
C2—C9—C10—C11179.9 (3)C14—C13—C18—C171.7 (4)
C9—C10—C11—C12178.8 (3)C12—C13—C18—C17178.2 (3)
 

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