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In the title compound, C14H21N2+·ClO4, the planar vinamidinium chain forms a dihedral angle of 84.0 (1)° with the benzene ring. The molecular packing is stabilized by C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005574/ci6343sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005574/ci6343Isup2.hkl
Contains datablock I

CCDC reference: 224413

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.075
  • wR factor = 0.272
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.272 PLAT084_ALERT_2_C High R2 Value .................................. 0.27 PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N2 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C7 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. O2 .. 2.81 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B .. O2 .. 2.75 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B .. O3 .. 2.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O1 .. 2.71 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O2 .. 2.84 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O1 .. 2.72 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A .. O4 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O1 .. 2.93 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. O1 .. 2.82 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A .. O4 .. 2.80 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. O3 .. 2.94 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C2 .. O2 .. 3.74 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C12 .. O3 .. 3.75 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C14 .. O4 .. 3.80 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C8 .. O1 .. 3.75 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C13 .. O3 .. 3.74 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 23 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 3 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 18 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: TEXSAN; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).

1-Dimethylamino-3-dimethyliminio-1-(p-methylphenyl)prop-1-ene perchlorate top
Crystal data top
C14H21N2+·ClO4F(000) = 672
Mr = 316.78Dx = 1.279 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yabCell parameters from 23 reflections
a = 11.601 (3) Åθ = 3.5–4.4°
b = 12.409 (2) ŵ = 0.25 mm1
c = 12.664 (4) ÅT = 293 K
β = 115.501 (18)°Prism, colourless
V = 1645.4 (8) Å30.3 × 0.2 × 0.1 mm
Z = 4
Data collection top
Rigaku AFC-7S
diffractometer
Rint = 0.100
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.4°
Graphite monochromatorh = 013
ω/2θ scansk = 014
3045 measured reflectionsl = 1513
2890 independent reflections3 standard reflections every 150 reflections
1649 reflections with I > 2σ(I) intensity decay: 10.4%
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)] = 0.075H-atom parameters constrained
wR(F2) = 0.272 w = 1/[σ2(Fo2) + (0.1546P)2 + 0.6164P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2890 reflectionsΔρmax = 0.42 e Å3
196 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (6)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.12016 (11)0.05315 (10)0.30803 (11)0.0833 (5)
O10.0698 (4)0.0370 (4)0.1861 (3)0.1204 (17)
O20.2334 (4)0.0085 (4)0.3626 (4)0.1298 (19)
O30.0295 (5)0.0235 (6)0.3464 (6)0.184 (3)
O40.1529 (5)0.1619 (4)0.3401 (6)0.167 (3)
N10.5578 (3)0.2068 (3)0.5990 (3)0.0693 (11)
N20.3312 (3)0.0200 (3)0.7511 (4)0.0757 (14)
C10.5356 (3)0.1663 (3)0.6848 (4)0.0613 (13)
C20.4400 (4)0.0893 (3)0.6651 (4)0.0640 (14)
C30.4172 (4)0.0519 (3)0.7572 (4)0.0691 (14)
C40.6177 (4)0.2060 (3)0.8052 (4)0.0632 (14)
C50.7372 (4)0.1592 (4)0.8715 (4)0.0729 (16)
C60.8126 (4)0.1988 (4)0.9822 (4)0.0818 (16)
C70.7739 (4)0.2824 (4)1.0295 (4)0.0761 (17)
C80.6550 (5)0.3270 (4)0.9645 (4)0.0853 (19)
C90.5787 (4)0.2888 (3)0.8544 (4)0.0807 (16)
C100.4834 (5)0.1744 (4)0.4761 (4)0.0838 (17)
C110.6599 (5)0.2837 (5)0.6178 (5)0.102 (2)
C120.2501 (5)0.0764 (4)0.6451 (5)0.092 (2)
C130.3169 (6)0.0492 (5)0.8578 (6)0.115 (3)
C140.8576 (6)0.3232 (5)1.1513 (5)0.109 (2)
H20.391740.063340.589920.0766*
H30.467710.080410.830710.0828*
H50.765570.101980.841400.0877*
H60.892000.167541.025730.0982*
H80.626420.383380.995370.1023*
H90.498800.319610.812250.0967*
H10A0.508580.217490.426570.1255*
H10B0.499200.099780.467130.1255*
H10C0.394100.184810.454490.1255*
H11A0.723660.250240.599540.1520*
H11B0.625390.345250.568200.1520*
H11C0.697740.306280.698170.1520*
H12A0.171020.095010.647710.1378*
H12B0.233210.030920.578770.1378*
H12C0.292230.140920.638440.1378*
H13A0.229380.040200.844130.1719*
H13B0.341660.123020.877440.1719*
H13C0.370290.003510.921140.1719*
H14A0.930110.276571.187800.1631*
H14B0.886240.394861.146550.1631*
H14C0.809530.324151.196930.1631*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0656 (7)0.0799 (9)0.0978 (10)0.0038 (5)0.0289 (6)0.0203 (6)
O10.135 (3)0.121 (3)0.078 (3)0.008 (3)0.020 (2)0.015 (2)
O20.106 (3)0.121 (3)0.136 (4)0.034 (3)0.027 (3)0.004 (3)
O30.127 (4)0.257 (7)0.202 (6)0.056 (4)0.102 (4)0.034 (5)
O40.146 (4)0.095 (3)0.225 (6)0.011 (3)0.048 (4)0.073 (4)
N10.061 (2)0.0560 (19)0.086 (2)0.0113 (15)0.0271 (18)0.0038 (17)
N20.067 (2)0.0590 (19)0.101 (3)0.0014 (18)0.036 (2)0.0135 (19)
C10.054 (2)0.0411 (18)0.083 (3)0.0051 (16)0.024 (2)0.0024 (18)
C20.053 (2)0.048 (2)0.084 (3)0.0023 (16)0.023 (2)0.0006 (19)
C30.057 (2)0.053 (2)0.091 (3)0.0040 (19)0.026 (2)0.009 (2)
C40.053 (2)0.049 (2)0.084 (3)0.0035 (16)0.026 (2)0.0010 (19)
C50.057 (2)0.066 (3)0.089 (3)0.0056 (19)0.025 (2)0.005 (2)
C60.055 (2)0.085 (3)0.092 (3)0.002 (2)0.019 (2)0.004 (3)
C70.074 (3)0.070 (3)0.079 (3)0.018 (2)0.028 (2)0.005 (2)
C80.081 (3)0.067 (3)0.097 (4)0.002 (2)0.028 (3)0.016 (2)
C90.066 (3)0.061 (2)0.098 (3)0.009 (2)0.019 (2)0.006 (2)
C100.083 (3)0.084 (3)0.075 (3)0.019 (3)0.025 (3)0.004 (2)
C110.099 (4)0.097 (4)0.100 (4)0.049 (3)0.034 (3)0.002 (3)
C120.082 (3)0.064 (3)0.132 (5)0.020 (2)0.048 (3)0.009 (3)
C130.103 (4)0.118 (5)0.134 (5)0.016 (3)0.061 (4)0.034 (4)
C140.099 (4)0.113 (4)0.093 (4)0.033 (3)0.021 (3)0.022 (3)
Geometric parameters (Å, º) top
Cl—O11.410 (4)C3—H30.9303
Cl—O21.417 (5)C5—H50.9305
Cl—O31.385 (7)C6—H60.9304
Cl—O41.413 (5)C8—H80.9294
N1—C11.319 (6)C9—H90.9296
N1—C101.474 (6)C10—H10A0.9604
N1—C111.459 (7)C10—H10B0.9601
N2—C31.316 (6)C10—H10C0.9595
N2—C121.446 (7)C11—H11A0.9593
N2—C131.476 (8)C11—H11B0.9600
C1—C21.402 (6)C11—H11C0.9604
C1—C41.491 (6)C12—H12A0.9603
C2—C31.383 (7)C12—H12B0.9596
C4—C51.401 (7)C12—H12C0.9605
C4—C91.375 (6)C13—H13A0.9602
C5—C61.384 (7)C13—H13B0.9602
C6—C71.367 (7)C13—H13C0.9595
C7—C81.382 (7)C14—H14A0.9598
C7—C141.513 (7)C14—H14B0.9602
C8—C91.375 (7)C14—H14C0.9605
C2—H20.9299
O3···C12i3.356 (9)H2···O22.8112
O4···C12ii3.416 (7)H2···C102.5352
O1···H9iii2.8152H2···C122.6803
O1···H5iv2.7048H2···H10B2.4178
O1···H6v2.7196H2···H10C2.2923
O2···H12B2.7526H2···H12B2.1323
O2···H5iv2.8366H3···C42.4586
O2···H22.8112H3···C53.0994
O3···H12Ai2.5207H3···C92.8464
O4···H10C2.5532H3···H13C2.1881
O4···H14Av2.8518H5···O1iv2.7048
O4···H12Cii2.5134H5···O2iv2.8366
O4···H10Avi2.7966H6···O1x2.7196
C2···C11vi3.424 (8)H6···H14A2.3361
C3···C93.418 (6)H9···O1ii2.8152
C3···C11vi3.413 (8)H10A···H11A2.5462
C5···C113.322 (8)H10A···H11B2.3396
C6···C13vii3.526 (9)H10A···O4viii2.7966
C7···C13vii3.580 (8)H10B···C22.8734
C9···C33.418 (6)H10B···H22.4178
C9···C113.507 (8)H10C···O42.5532
C11···C2viii3.424 (8)H10C···C22.7530
C11···C93.507 (8)H10C···H22.2923
C11···C3viii3.413 (8)H11A···H10A2.5462
C11···C53.322 (8)H11A···C2viii3.0263
C12···O3i3.356 (9)H11B···H10A2.3396
C12···O4iii3.416 (7)H11B···H12Bviii2.5974
C13···C6vii3.526 (9)H11C···C42.3090
C13···C7vii3.580 (8)H11C···C52.7375
C2···H10B2.8734H11C···C92.8673
C2···H12B2.6301H11C···C3viii2.9153
C2···H11Avi3.0263H12A···H13A2.3787
C2···H10C2.7530H12A···O3i2.5207
C3···H14Bix2.8442H12B···O22.7526
C3···H11Cvi2.9153H12B···C22.6301
C4···H32.4586H12B···H22.1323
C4···H11C2.3090H12B···H11Bvi2.5974
C5···H11C2.7375H12C···O4iii2.5134
C5···H33.0994H13A···H12A2.3787
C7···H13Bvii2.9083H13B···C7vii2.9083
C9···H32.8464H13C···H32.1881
C9···H11C2.8673H14A···O4x2.8518
C10···H22.5352H14A···H62.3361
C12···H22.6803H14B···C3xi2.8442
O1—Cl—O2108.5 (3)C7—C8—H8119.76
O1—Cl—O3109.1 (4)C9—C8—H8119.71
O1—Cl—O4112.6 (4)C4—C9—H9119.23
O2—Cl—O3111.7 (4)C8—C9—H9119.21
O2—Cl—O4107.3 (3)N1—C10—H10A109.47
O3—Cl—O4107.7 (4)N1—C10—H10B109.46
C1—N1—C10122.2 (4)N1—C10—H10C109.51
C1—N1—C11123.2 (4)H10A—C10—H10B109.42
C10—N1—C11114.6 (4)H10A—C10—H10C109.47
C3—N2—C12123.8 (4)H10B—C10—H10C109.50
C3—N2—C13119.6 (5)N1—C11—H11A109.50
C12—N2—C13116.5 (4)N1—C11—H11B109.46
N1—C1—C2122.2 (4)N1—C11—H11C109.41
N1—C1—C4116.8 (4)H11A—C11—H11B109.53
C2—C1—C4121.0 (4)H11A—C11—H11C109.49
C1—C2—C3120.2 (4)H11B—C11—H11C109.44
N2—C3—C2126.4 (4)N2—C12—H12A109.51
C1—C4—C5120.5 (4)N2—C12—H12B109.52
C1—C4—C9121.3 (4)N2—C12—H12C109.44
C5—C4—C9118.2 (4)H12A—C12—H12B109.48
C4—C5—C6119.4 (4)H12A—C12—H12C109.41
C5—C6—C7122.0 (5)H12B—C12—H12C109.47
C6—C7—C8118.4 (4)N2—C13—H13A109.47
C6—C7—C14120.9 (5)N2—C13—H13B109.42
C8—C7—C14120.8 (5)N2—C13—H13C109.50
C7—C8—C9120.5 (5)H13A—C13—H13B109.44
C4—C9—C8121.6 (5)H13A—C13—H13C109.50
C1—C2—H2119.97H13B—C13—H13C109.49
C3—C2—H2119.86C7—C14—H14A109.51
N2—C3—H3116.85C7—C14—H14B109.49
C2—C3—H3116.72C7—C14—H14C109.48
C4—C5—H5120.28H14A—C14—H14B109.47
C6—C5—H5120.33H14A—C14—H14C109.46
C5—C6—H6119.00H14B—C14—H14C109.42
C7—C6—H6119.01
C10—N1—C1—C20.3 (6)C1—C2—C3—N2179.8 (4)
C11—N1—C1—C2177.5 (4)C1—C4—C5—C6178.8 (4)
C10—N1—C1—C4180.0 (4)C5—C4—C9—C81.4 (7)
C11—N1—C1—C42.3 (6)C1—C4—C9—C8178.8 (4)
C12—N2—C3—C23.6 (7)C9—C4—C5—C61.4 (7)
C13—N2—C3—C2178.4 (5)C4—C5—C6—C70.2 (8)
N1—C1—C4—C995.5 (5)C5—C6—C7—C80.9 (8)
C2—C1—C4—C595.1 (6)C5—C6—C7—C14179.3 (5)
N1—C1—C4—C584.7 (5)C14—C7—C8—C9179.2 (5)
C2—C1—C4—C984.7 (5)C6—C7—C8—C90.9 (8)
N1—C1—C2—C3177.7 (4)C7—C8—C9—C40.3 (8)
C4—C1—C2—C32.5 (6)
Symmetry codes: (i) x, y, z+1; (ii) x+1/2, y+1/2, z+1; (iii) x+1/2, y1/2, z+1; (iv) x+1, y, z+1; (v) x1, y, z1; (vi) x1/2, y+1/2, z; (vii) x+1, y, z+2; (viii) x+1/2, y+1/2, z; (ix) x+3/2, y1/2, z+2; (x) x+1, y, z+1; (xi) x+3/2, y+1/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.813.740 (6)177
C10—H10C···O40.962.553.465 (9)159
C12—H12B···O20.962.753.599 (9)147
C12—H12B···O30.962.953.750 (8)141
C5—H5···O1iv0.932.713.589 (7)159
C5—H5···O2iv0.932.843.643 (8)146
C6—H6···O1x0.932.723.601 (6)158
C14—H14A···O4x0.962.853.796 (8)168
C8—H8···O1xii0.932.933.754 (8)148
C9—H9···O1ii0.932.823.458 (6)127
C10—H10A···O4viii0.962.803.725 (10)163
C13—H13A···O3i0.962.943.740 (8)142
C12—H12A···O3i0.962.523.356 (9)145
C12—H12C···O4iii0.962.513.416 (7)156
Symmetry codes: (i) x, y, z+1; (ii) x+1/2, y+1/2, z+1; (iii) x+1/2, y1/2, z+1; (iv) x+1, y, z+1; (viii) x+1/2, y+1/2, z; (x) x+1, y, z+1; (xii) x+1/2, y+1/2, z+1.
 

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