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The structure of the title compound, (C6H17N2)[SnCl2(CH3)2], shows an anion-cation contact via a hydrogen bond. The stannate anion is five-coordinate. There are two cations and two anions in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013205/bt6286sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013205/bt6286Isup2.hkl
Contains datablock I

CCDC reference: 217384

Key indicators

  • Single-crystal X-ray study
  • T = 140 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.033
  • wR factor = 0.085
  • Data-to-parameter ratio = 22.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
CELLV_02 Alert C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 13.63 Cell volume su given = 11.00 WEIGH_01 Alert C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0411P)^2^] wher Weighting scheme identified as calc PLAT_353 Alert C Long N-H Bond (0.87A) N1 - H1 = 1.02 Ang. General Notes
REFLE_01 _reflns_observed_criterion is an old dataname which has been superseded by _reflns_threshold_expression REFLG_01 _reflns_number_observed is an old dataname which has been superseded by _reflns_number_gt
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Comment top

(2-Dimethylaminoethyl)dimethylammonium dichlorotrimethyltin, (I), crystallizes in the monoclinic space group P21/c with eight molecules per unit cell. The asymmetric unit consists of two almost identical molecules. The Sn atom is five-coordinate. A hydrogen bond between the ions shows interatomic distances of N—H 0.= 951 (4) Å and Cl—H = 2.287 Å. For comparison, 2,2'-iminodipyridinium dichlorotriphenyltin shows a Cl—H bond length of 2.291 Å (Ng, 1999). The bond length and angles of (I) are in good agreement with those of bis(trimethylstannyl)ammonium dichlorotrimethyltin (Hillwig et al., 1997) and 2,2,6,6-tetramethylpiperidinium dichlorotrimethyltin (Johnson et al., 1991).

Experimental top

The title compound was isolated as a byproduct after a reaction of HCl formed in an elimination reaction with traces of chlorotrimethyltin and TMEDA. It was isolated after crystallization from toluene at 253 K as colourless needles.

Refinement top

Atoms H1* and H3* were located in a difference map and were allowed to refine freely. The methyl groups in the anion were allowed to rotate about the Sn—C bond.

Computing details top

Data collection: MSC R-AXIS-II control software; cell refinement: DENZO (Otwinowski & Minor, 1985); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1985); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of (I). Displacement ellipsoids are drawn here at the 50% probability level.
(2-Dimethylaminoethyl)dimethylammonium dichlorotrimethyltin top
Crystal data top
(C6H17N2)[SnCl2(CH3)2]F(000) = 1424
Mr = 351.91Dx = 1.423 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.480 (3) ÅCell parameters from 225 reflections
b = 12.278 (3) Åθ = 2.7–22.7°
c = 19.366 (4) ŵ = 1.86 mm1
β = 107.41 (3)°T = 140 K
V = 3285.3 (11) Å3Needle, colourless
Z = 80.3 × 0.1 × 0.1 mm
Data collection top
Rigaku R-AXIS-IIc
diffractometer
4747 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.027
Graphite monochromatorθmax = 25.4°, θmin = 2.0°
image–plate oscillation photos scansh = 1717
11409 measured reflectionsk = 1414
6025 independent reflectionsl = 2323
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.03Calculated w = 1/[σ2(Fo2) + (0.0411P)2]
where P = (Fo2 + 2Fc2)/3
6025 reflections(Δ/σ)max = 0.009
267 parametersΔρmax = 0.90 e Å3
0 restraintsΔρmin = 0.92 e Å3
Crystal data top
(C6H17N2)[SnCl2(CH3)2]V = 3285.3 (11) Å3
Mr = 351.91Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.480 (3) ŵ = 1.86 mm1
b = 12.278 (3) ÅT = 140 K
c = 19.366 (4) Å0.3 × 0.1 × 0.1 mm
β = 107.41 (3)°
Data collection top
Rigaku R-AXIS-IIc
diffractometer
4747 reflections with I > 2σ(I)
11409 measured reflectionsRint = 0.027
6025 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.90 e Å3
6025 reflectionsΔρmin = 0.92 e Å3
267 parameters
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
Sn20.014081 (19)0.556680 (19)0.251070 (14)0.03232 (9)
Cl30.03415 (7)0.55849 (8)0.39133 (5)0.0421 (2)
Cl40.01007 (7)0.55207 (7)0.11094 (5)0.0386 (2)
C40.1273 (3)0.4902 (3)0.2314 (2)0.0403 (9)
H4A0.13130.45220.27370.060*
H4B0.14030.44050.19140.060*
H4C0.17410.54800.22020.060*
C50.0282 (4)0.7292 (3)0.2528 (2)0.0624 (14)
H5A0.00240.75720.20460.094*
H5B0.09530.74850.27150.094*
H5C0.00670.75980.28330.094*
C60.1467 (3)0.4674 (3)0.2713 (2)0.0475 (10)
H6A0.17260.47700.23150.071*
H6B0.13460.39140.27660.071*
H6C0.19250.49370.31490.071*
Sn10.501915 (18)0.92434 (2)0.226317 (14)0.03468 (9)
Cl10.35102 (8)0.93494 (8)0.10841 (7)0.0548 (3)
Cl20.64762 (8)0.91704 (8)0.34484 (6)0.0548 (3)
C10.5313 (3)0.7642 (3)0.1968 (2)0.0523 (11)
H1A0.47670.73770.15900.078*
H1B0.54310.71710.23810.078*
H1C0.58740.76540.18010.078*
C20.5652 (3)1.0560 (3)0.1852 (2)0.0515 (11)
H2A0.63031.06710.21560.077*
H2B0.52801.12090.18470.077*
H2C0.56571.03940.13690.077*
C30.4076 (3)0.9478 (3)0.2907 (3)0.0567 (12)
H3A0.42561.01300.31890.085*
H3B0.41240.88660.32250.085*
H3C0.34220.95440.25990.085*
N30.1938 (2)1.2334 (2)0.08305 (17)0.0353 (7)
H1*0.254 (3)0.788 (3)0.068 (2)0.053 (12)*
C310.1171 (3)1.3175 (3)0.0753 (2)0.0459 (10)
H31A0.10231.35020.02820.069*
H31B0.13981.37250.11170.069*
H31C0.05991.28410.08100.069*
C320.2174 (3)1.1817 (3)0.1561 (2)0.0515 (11)
H32A0.26671.12760.16060.077*
H32B0.16041.14800.16200.077*
H32C0.24031.23640.19270.077*
C330.1679 (3)1.1484 (3)0.0248 (2)0.0464 (10)
H33A0.20871.08490.04000.056*
H33B0.10111.12620.01600.056*
N40.2776 (3)1.2438 (3)0.0287 (2)0.0508 (9)
C410.3548 (4)1.1639 (5)0.0235 (3)0.0865 (18)
H41A0.35521.11160.01340.130*
H41B0.41611.20060.01150.130*
H41C0.34341.12730.06910.130*
C420.2776 (4)1.3220 (3)0.0848 (3)0.0657 (14)
H42A0.34081.35390.07480.099*
H42B0.23101.37800.08580.099*
H42C0.26111.28570.13080.099*
C430.1816 (3)1.1943 (4)0.0431 (2)0.0525 (11)
H43A0.17431.13670.07860.063*
H43B0.13231.24870.06310.063*
H3*0.251 (3)1.267 (3)0.077 (2)0.046 (12)*
N10.1964 (2)0.7465 (3)0.07453 (17)0.0373 (7)
C110.1200 (3)0.8252 (3)0.0782 (2)0.0472 (10)
H11A0.09730.86360.03310.071*
H11B0.14620.87620.11660.071*
H11C0.06710.78660.08710.071*
C120.2337 (3)0.6854 (3)0.1429 (2)0.0561 (12)
H12A0.28260.63520.13890.084*
H12B0.18170.64590.15260.084*
H12C0.26100.73530.18180.084*
C130.1587 (3)0.6754 (4)0.0086 (3)0.0554 (12)
H13A0.11170.62470.01670.066*
H13B0.12600.72060.03250.066*
N20.3215 (3)0.6824 (3)0.0040 (2)0.0619 (11)
C210.3063 (4)0.7594 (5)0.0644 (3)0.0825 (17)
H21A0.25030.80320.06740.124*
H21B0.29640.71970.10870.124*
H21C0.36200.80540.05650.124*
C220.4052 (4)0.6144 (5)0.0026 (3)0.0790 (16)
H22A0.41320.56490.04230.118*
H22B0.46180.65930.01110.118*
H22C0.39620.57390.04130.118*
C230.2368 (3)0.6133 (4)0.0087 (3)0.0600 (13)
H23A0.25620.55280.02470.072*
H23B0.21240.58370.05720.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn20.03840 (16)0.02992 (14)0.02921 (15)0.00226 (10)0.01097 (11)0.00064 (10)
Cl30.0476 (6)0.0504 (6)0.0279 (5)0.0076 (4)0.0108 (4)0.0009 (4)
Cl40.0421 (6)0.0464 (5)0.0284 (5)0.0026 (4)0.0121 (4)0.0043 (4)
C40.038 (2)0.050 (2)0.034 (2)0.0006 (17)0.0138 (18)0.0020 (18)
C50.108 (4)0.028 (2)0.059 (3)0.001 (2)0.036 (3)0.002 (2)
C60.041 (2)0.064 (3)0.037 (2)0.013 (2)0.0103 (19)0.007 (2)
Sn10.03152 (15)0.03421 (15)0.03855 (16)0.00027 (10)0.01087 (12)0.00076 (11)
Cl10.0468 (6)0.0418 (5)0.0607 (7)0.0034 (4)0.0070 (5)0.0031 (5)
Cl20.0521 (7)0.0546 (6)0.0465 (6)0.0114 (5)0.0023 (5)0.0058 (5)
C10.056 (3)0.040 (2)0.058 (3)0.0089 (19)0.012 (2)0.003 (2)
C20.051 (3)0.049 (2)0.054 (3)0.0102 (19)0.017 (2)0.003 (2)
C30.054 (3)0.063 (3)0.062 (3)0.007 (2)0.030 (2)0.005 (2)
N30.0312 (18)0.0416 (17)0.0321 (17)0.0020 (14)0.0081 (14)0.0004 (14)
C310.043 (2)0.047 (2)0.044 (2)0.0075 (18)0.0065 (19)0.0032 (19)
C320.054 (3)0.052 (2)0.042 (3)0.005 (2)0.005 (2)0.015 (2)
C330.046 (3)0.046 (2)0.049 (3)0.0095 (19)0.017 (2)0.008 (2)
N40.049 (2)0.053 (2)0.056 (2)0.0063 (17)0.0239 (19)0.0067 (18)
C410.070 (4)0.094 (4)0.102 (5)0.014 (3)0.037 (4)0.045 (4)
C420.070 (3)0.057 (3)0.079 (4)0.007 (2)0.037 (3)0.013 (3)
C430.054 (3)0.065 (3)0.040 (3)0.002 (2)0.017 (2)0.008 (2)
N10.0336 (19)0.0419 (17)0.0357 (18)0.0000 (14)0.0093 (15)0.0030 (15)
C110.046 (3)0.055 (2)0.041 (2)0.0108 (19)0.013 (2)0.004 (2)
C120.049 (3)0.058 (3)0.056 (3)0.002 (2)0.006 (2)0.019 (2)
C130.045 (3)0.061 (3)0.060 (3)0.011 (2)0.014 (2)0.025 (2)
N20.064 (3)0.077 (3)0.055 (3)0.033 (2)0.034 (2)0.016 (2)
C210.086 (4)0.098 (4)0.074 (4)0.007 (3)0.039 (3)0.010 (3)
C220.071 (4)0.094 (4)0.080 (4)0.012 (3)0.036 (3)0.011 (3)
C230.060 (3)0.065 (3)0.057 (3)0.015 (2)0.022 (3)0.019 (2)
Geometric parameters (Å, º) top
Sn2—C52.127 (4)C33—C431.498 (6)
Sn2—C42.130 (4)C33—H33A0.9700
Sn2—C62.143 (4)C33—H33B0.9700
Sn2—Cl42.6311 (11)N4—C421.449 (5)
Sn2—Cl32.6441 (11)N4—C431.466 (5)
C4—H4A0.9600N4—C411.467 (6)
C4—H4B0.9600C41—H41A0.9600
C4—H4C0.9600C41—H41B0.9600
C5—H5A0.9600C41—H41C0.9600
C5—H5B0.9600C42—H42A0.9600
C5—H5C0.9600C42—H42B0.9600
C6—H6A0.9600C42—H42C0.9600
C6—H6B0.9600C43—H43A0.9700
C6—H6C0.9600C43—H43B0.9700
Sn1—C12.126 (4)N1—C121.477 (5)
Sn1—C32.126 (4)N1—C111.486 (5)
Sn1—C22.126 (4)N1—C131.508 (5)
Sn1—Cl22.6135 (15)N1—H1*1.02 (4)
Sn1—Cl12.6494 (15)C11—H11A0.9600
C1—H1A0.9600C11—H11B0.9600
C1—H1B0.9600C11—H11C0.9600
C1—H1C0.9600C12—H12A0.9600
C2—H2A0.9600C12—H12B0.9600
C2—H2B0.9600C12—H12C0.9600
C2—H2C0.9600C13—C231.482 (6)
C3—H3A0.9600C13—H13A0.9700
C3—H3B0.9600C13—H13B0.9700
C3—H3C0.9600N2—C221.445 (6)
N3—C311.491 (5)N2—C211.468 (6)
N3—C321.494 (5)N2—C231.472 (5)
N3—C331.499 (5)C21—H21A0.9600
N3—H3*0.96 (4)C21—H21B0.9600
C31—H31A0.9600C21—H21C0.9600
C31—H31B0.9600C22—H22A0.9600
C31—H31C0.9600C22—H22B0.9600
C32—H32A0.9600C22—H22C0.9600
C32—H32B0.9600C23—H23A0.9700
C32—H32C0.9600C23—H23B0.9700
C5—Sn2—C4117.85 (18)H32B—C32—H32C109.5
C5—Sn2—C6115.46 (19)C43—C33—N3109.3 (3)
C4—Sn2—C6126.68 (17)C43—C33—H33A109.8
C5—Sn2—Cl491.18 (12)N3—C33—H33A109.8
C4—Sn2—Cl489.04 (11)C43—C33—H33B109.8
C6—Sn2—Cl490.74 (12)N3—C33—H33B109.8
C5—Sn2—Cl389.69 (12)H33A—C33—H33B108.3
C4—Sn2—Cl389.50 (11)C42—N4—C43110.1 (4)
C6—Sn2—Cl389.96 (12)C42—N4—C41108.9 (4)
Cl4—Sn2—Cl3178.53 (3)C43—N4—C41113.3 (4)
Sn2—C4—H4A109.5N4—C41—H41A109.5
Sn2—C4—H4B109.5N4—C41—H41B109.5
H4A—C4—H4B109.5H41A—C41—H41B109.5
Sn2—C4—H4C109.5N4—C41—H41C109.5
H4A—C4—H4C109.5H41A—C41—H41C109.5
H4B—C4—H4C109.5H41B—C41—H41C109.5
Sn2—C5—H5A109.5N4—C42—H42A109.5
Sn2—C5—H5B109.5N4—C42—H42B109.5
H5A—C5—H5B109.5H42A—C42—H42B109.5
Sn2—C5—H5C109.5N4—C42—H42C109.5
H5A—C5—H5C109.5H42A—C42—H42C109.5
H5B—C5—H5C109.5H42B—C42—H42C109.5
Sn2—C6—H6A109.5N4—C43—C33110.8 (3)
Sn2—C6—H6B109.5N4—C43—H43A109.5
H6A—C6—H6B109.5C33—C43—H43A109.5
Sn2—C6—H6C109.5N4—C43—H43B109.5
H6A—C6—H6C109.5C33—C43—H43B109.5
H6B—C6—H6C109.5H43A—C43—H43B108.1
C1—Sn1—C3119.88 (17)C12—N1—C11111.4 (3)
C1—Sn1—C2117.36 (17)C12—N1—C13114.1 (3)
C3—Sn1—C2122.71 (17)C11—N1—C13109.3 (3)
C1—Sn1—Cl291.74 (12)C12—N1—H1*106 (2)
C3—Sn1—Cl288.91 (14)C11—N1—H1*110 (2)
C2—Sn1—Cl291.71 (13)C13—N1—H1*106 (2)
C1—Sn1—Cl189.64 (12)N1—C11—H11A109.5
C3—Sn1—Cl189.43 (14)N1—C11—H11B109.5
C2—Sn1—Cl188.66 (13)H11A—C11—H11B109.5
Cl2—Sn1—Cl1178.22 (4)N1—C11—H11C109.5
Sn1—C1—H1A109.5H11A—C11—H11C109.5
Sn1—C1—H1B109.5H11B—C11—H11C109.5
H1A—C1—H1B109.5N1—C12—H12A109.5
Sn1—C1—H1C109.5N1—C12—H12B109.5
H1A—C1—H1C109.5H12A—C12—H12B109.5
H1B—C1—H1C109.5N1—C12—H12C109.5
Sn1—C2—H2A109.5H12A—C12—H12C109.5
Sn1—C2—H2B109.5H12B—C12—H12C109.5
H2A—C2—H2B109.5C23—C13—N1112.5 (4)
Sn1—C2—H2C109.5C23—C13—H13A109.1
H2A—C2—H2C109.5N1—C13—H13A109.1
H2B—C2—H2C109.5C23—C13—H13B109.1
Sn1—C3—H3A109.5N1—C13—H13B109.1
Sn1—C3—H3B109.5H13A—C13—H13B107.8
H3A—C3—H3B109.5C22—N2—C21111.4 (4)
Sn1—C3—H3C109.5C22—N2—C23109.5 (4)
H3A—C3—H3C109.5C21—N2—C23113.4 (4)
H3B—C3—H3C109.5N2—C21—H21A109.5
C31—N3—C32110.0 (3)N2—C21—H21B109.5
C31—N3—C33113.3 (3)H21A—C21—H21B109.5
C32—N3—C33110.6 (3)N2—C21—H21C109.5
C31—N3—H3*110 (2)H21A—C21—H21C109.5
C32—N3—H3*109 (2)H21B—C21—H21C109.5
C33—N3—H3*104 (2)N2—C22—H22A109.5
N3—C31—H31A109.5N2—C22—H22B109.5
N3—C31—H31B109.5H22A—C22—H22B109.5
H31A—C31—H31B109.5N2—C22—H22C109.5
N3—C31—H31C109.5H22A—C22—H22C109.5
H31A—C31—H31C109.5H22B—C22—H22C109.5
H31B—C31—H31C109.5N2—C23—C13111.6 (4)
N3—C32—H32A109.5N2—C23—H23A109.3
N3—C32—H32B109.5C13—C23—H23A109.3
H32A—C32—H32B109.5N2—C23—H23B109.3
N3—C32—H32C109.5C13—C23—H23B109.3
H32A—C32—H32C109.5H23A—C23—H23B108.0

Experimental details

Crystal data
Chemical formula(C6H17N2)[SnCl2(CH3)2]
Mr351.91
Crystal system, space groupMonoclinic, P21/c
Temperature (K)140
a, b, c (Å)14.480 (3), 12.278 (3), 19.366 (4)
β (°) 107.41 (3)
V3)3285.3 (11)
Z8
Radiation typeMo Kα
µ (mm1)1.86
Crystal size (mm)0.3 × 0.1 × 0.1
Data collection
DiffractometerRigaku R-AXIS-IIc
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11409, 6025, 4747
Rint0.027
(sin θ/λ)max1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.085, 1.03
No. of reflections6025
No. of parameters267
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.90, 0.92

Computer programs: MSC R-AXIS-II control software, DENZO (Otwinowski & Minor, 1985), DENZO and SCALEPACK (Otwinowski & Minor, 1985), SHELXTL (Sheldrick, 1997), SHELXTL.

 

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