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The title compound, C13H30N3+·Cl-, is a phase-transfer catalyst. The geometry at the central C atom of the guanidinium cation, which lies on a twofold rotation axis, is almost ideal trigonal planar, with N-C-N angles of 119.8 (2) and 120.08 (11)°. The chloride anion also lies on a twofold rotation axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028364/hg2047sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028364/hg2047Isup2.hkl
Contains datablock I

CCDC reference: 618967

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.139
  • Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.

Hexaethylguanidinium chloride top
Crystal data top
C13H30N3+·ClF(000) = 584
Mr = 262.86Dx = 1.077 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 7.3110 (15) Åθ = 10–14°
b = 16.274 (3) ŵ = 0.22 mm1
c = 13.802 (3) ÅT = 293 K
β = 97.77 (3)°Block, white
V = 1627.1 (6) Å30.40 × 0.20 × 0.20 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1191 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 26.0°, θmin = 2.5°
ω/2θ scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 020
Tmin = 0.916, Tmax = 0.957l = 1616
1710 measured reflections3 standard reflections every 200 reflections
1582 independent reflections intensity decay: none
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.07P)2 + 0.96P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1582 reflectionsΔρmax = 0.28 e Å3
80 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (2)
Special details top

Experimental. Spectroscopic analysis, 1H NMR (CDCl3, δ, p.p.m.): 1.5 (t, 3H), 1.4 (t, 1H), 2.9 (q, 1H), 3.2 (m, 1 H), 3.6 (m, 1H).

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
Cl0.00000.29804 (7)0.75000.0777 (4)
N10.50000.21906 (13)0.75000.0360 (5)
N20.4707 (2)0.34241 (9)0.66536 (11)0.0353 (4)
C10.50000.30115 (15)0.75000.0310 (6)
C20.6623 (4)0.37726 (17)0.5362 (2)0.0705 (8)
H2A0.70900.35520.47990.106*
H2B0.76370.39280.58440.106*
H2C0.58750.42460.51750.106*
C30.2620 (3)0.11004 (15)0.7258 (2)0.0676 (7)
H3A0.18180.08130.67630.101*
H3B0.18950.13720.76920.101*
H3C0.34420.07160.76210.101*
C40.2071 (3)0.41784 (16)0.57329 (17)0.0570 (6)
H4A0.14110.46890.57150.085*
H4B0.12430.37340.58160.085*
H4C0.25740.41070.51310.085*
C50.5470 (3)0.31281 (13)0.57880 (15)0.0486 (6)
H5A0.44640.29640.52940.058*
H5B0.62260.26470.59640.058*
C60.3727 (3)0.17285 (13)0.67829 (16)0.0468 (5)
H6A0.44300.14520.63320.056*
H6B0.28890.21100.64090.056*
C70.3624 (3)0.41870 (12)0.65798 (14)0.0413 (5)
H7A0.44370.46460.65000.050*
H7B0.31080.42700.71840.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0511 (5)0.0848 (7)0.1008 (8)0.0000.0235 (5)0.000
N10.0369 (12)0.0322 (11)0.0381 (12)0.0000.0022 (9)0.000
N20.0362 (8)0.0346 (8)0.0350 (8)0.0016 (6)0.0043 (6)0.0021 (7)
C10.0225 (11)0.0326 (13)0.0376 (14)0.0000.0037 (10)0.000
C20.0666 (16)0.0807 (18)0.0701 (17)0.0052 (14)0.0311 (14)0.0197 (14)
C30.0617 (15)0.0540 (14)0.0862 (19)0.0210 (12)0.0070 (13)0.0011 (13)
C40.0445 (12)0.0632 (15)0.0588 (14)0.0041 (10)0.0090 (10)0.0093 (11)
C50.0574 (13)0.0510 (12)0.0395 (11)0.0046 (10)0.0140 (9)0.0023 (9)
C60.0500 (12)0.0391 (11)0.0499 (12)0.0072 (9)0.0016 (9)0.0057 (9)
C70.0393 (11)0.0362 (10)0.0465 (11)0.0036 (8)0.0015 (8)0.0045 (8)
Geometric parameters (Å, º) top
N1—C11.336 (3)C3—H3B0.9600
N1—C61.470 (2)C3—H3C0.9600
N2—C11.3393 (19)C4—C71.516 (3)
N2—C51.467 (2)C4—H4A0.9600
N2—C71.469 (2)C4—H4B0.9600
C1—N2i1.3393 (19)C4—H4C0.9600
C2—C51.514 (3)C5—H5A0.9700
C2—H2A0.9600C5—H5B0.9700
C2—H2B0.9600C6—H6A0.9700
C2—H2C0.9600C6—H6B0.9700
C3—C61.507 (3)C7—H7A0.9700
C3—H3A0.9600C7—H7B0.9700
C1—N1—C6120.76 (11)H4A—C4—H4B109.5
C6—N1—C6i118.5 (2)C7—C4—H4C109.5
C1—N2—C5120.81 (15)H4A—C4—H4C109.5
C1—N2—C7120.37 (15)H4B—C4—H4C109.5
C5—N2—C7118.82 (15)N2—C5—C2112.45 (18)
N1—C1—N2i120.09 (11)N2—C5—H5A109.1
N1—C1—N2120.08 (11)C2—C5—H5A109.1
N2i—C1—N2119.8 (2)N2—C5—H5B109.1
C5—C2—H2A109.5C2—C5—H5B109.1
C5—C2—H2B109.5H5A—C5—H5B107.8
H2A—C2—H2B109.5N1—C6—C3112.48 (17)
C5—C2—H2C109.5N1—C6—H6A109.1
H2A—C2—H2C109.5C3—C6—H6A109.1
H2B—C2—H2C109.5N1—C6—H6B109.1
C6—C3—H3A109.5C3—C6—H6B109.1
C6—C3—H3B109.5H6A—C6—H6B107.8
H3A—C3—H3B109.5N2—C7—C4112.72 (17)
C6—C3—H3C109.5N2—C7—H7A109.0
H3A—C3—H3C109.5C4—C7—H7A109.0
H3B—C3—H3C109.5N2—C7—H7B109.0
C7—C4—H4A109.5C4—C7—H7B109.0
C7—C4—H4B109.5H7A—C7—H7B107.8
C6—N1—C1—N2i143.71 (13)C1—N2—C5—C2125.3 (2)
C6i—N1—C1—N2i36.29 (13)C7—N2—C5—C254.2 (3)
C6—N1—C1—N236.29 (13)C1—N1—C6—C3127.42 (15)
C5—N2—C1—N138.05 (18)C6i—N1—C6—C352.58 (15)
C7—N2—C1—N1142.47 (12)C1—N2—C7—C4127.80 (18)
C5—N2—C1—N2i141.95 (18)C5—N2—C7—C452.7 (2)
C7—N2—C1—N2i37.53 (12)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···N10.972.522.872 (2)101
C6—H6B···N20.972.522.863 (3)101
C7—H7B···N2i0.972.522.858 (3)101
Symmetry code: (i) x+1, y, z+3/2.
 

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