N-[Bis(dimethyl­amino)­methyl­idene]-2-[(triphenyl­meth­yl)sulfan­yl]ethanaminium hexa­fluoro­phosphate

Neuba, A.; Flörke, U.; Henkel, G.

doi:10.1107/S1600536811014929

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1238-o1239

doi:10.1107/S1600536811014929

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N-[Bis(dimethylamino)methylidene]-2-[(triphenylmethyl)sulfanyl]ethanaminium hexafluorophosphate

Adam Neuba,^a Ulrich Flörke ^a ^* and Gerald Henkel ^a

^aDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: ulrich.floerke@upb.de

(Received 30 March 2011; accepted 20 April 2011; online 29 April 2011)

The molecular structure of the title compound, C₂₆H₃₂N₃S⁺·PF₆⁻, shows a protonated guanidyl group bridged by an ethylene linker with a tritylsulfanyl unit. The guanidinium (gua) unit displays charge delocalization over the three N—C_gua bonds. The N—C—C—S group shows a folded nonplanar conformation with a torsion angle of 158.4 (1)°. In the crystal, the cation and anion are linked by an N—H⋯F interaction.

Related literature

For the synthesis, see: Herres-Pawlis et al. (2005 ). For related structures, see: Flörke et al. (2006 ); Neuba et al. (2007c ); Pruszynski et al. (1992 ). For related chemistry literature, see: Börner et al. (2007 , 2009 ); Galezowski et al. (1994 ); Harmjanz (1997 ); Herres et al. (2005 ); Herres-Pawlis et al. (2009 ); Neuba (2009 ); Neuba et al. (2007a ,b , 2008a ,b , 2010 , 2011 ); Peters et al. (2008 ); Pohl et al. (2000 ); Raab et al. (2003 ); Schneider (2000 ); Waden (1999 ); Wittman (1999 ); Wittmann et al. (2001 ).

Experimental

Crystal data

C₂₆H₃₂N₃S⁺·PF₆⁻
M_r = 563.58
Triclinic, $[P \overline 1]$
a = 9.0111 (14) Å
b = 9.1376 (15) Å
c = 17.564 (3) Å
α = 96.532 (3)°
β = 100.225 (4)°
γ = 108.053 (3)°
V = 1331.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 120 K
0.33 × 0.30 × 0.26 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.924, T_max = 0.939
11922 measured reflections
6281 independent reflections
4547 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.104
S = 0.96
6281 reflections
338 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯F6ⁱ	0.88	2.13	2.949 (2)	155
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014929/bt5504sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014929/bt5504Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811014929/bt5504Isup3.cml

checkCIF report

Comment top

The synthesis and characterization of novel molecules containing nitrogen and sulfur as donor functions and their application in synthesis of sulfur copper complexes is important for biomimetic copper–sulfur chemistry. In search of multifunctional ligands we have extended our studies to guanidyl-type systems with N-donor functions. The first derivative, the ligand bis(tetramethyl-guanidino)propylene as well as amine guanidine hybrids and their complexes with Cu, Fe, Ni, Ag, Mn, Co and Zn have recently been investigated (Harmjanz, 1997; Waden, 1999; Pohl et al., 2000; Schneider, 2000; Wittmann et al., 2001; Herres-Pawlis et al., 2005, 2009; Herres et al., 2005; Neuba et al., 2008a,b, 2010; Börner et al. 2007, 2009). We have now developed several sulfur guanidine hybrids based on aminothiophenol and cysteamine (Neuba et al., 2007a,b,c; Neuba, 2009). The synthesized sulfur guanidine compounds possess aliphatic and aromatic thioethers or disulfide groups and were used in the synthesis of copper thiolate complexes to mimic active centres like the CuA in cytochrome-c oxidase and N₂O-reductase (Neuba et al., 2011). The title compound (I) is the protonated variant of 1,1,3,3-Tetramethyl-2-[2-(tritylsulfanyl)-ethyl]guanidine (C₂₆H₃₁N₃) (Neuba et al., 2007c). Both compounds possess a folded non-planar conformation with torsion angles of the S—C—C—N group of 66.04 (15) in C₂₆H₃₁N₃ and 158.36 (13)° in I. Compared to C₂₆H₃₂N₃ with localized N═C_gua double bond (N═C_gua: 1.281 (2), N—C_gua: 1.399 (2) and 1.292 (2) Å) the respective double bond in I is clearly delocalized over the guanidine unit (N═C_gua: 1.341 (2), N—C_gua: 1.3938 (2) and 1.333 (2) Å). Several variants of protonated bis(tetramethyl-guanidino)propylene (Flörke et al., 2006) show similar N—C (1.326 (7)–1.341 (6) Å) and N—C_gua bond lengths (1.331 (2)–1.343 (3) Å). In bis(tetramethylguanidino)biphenyl (Pruszynski et al., 1992), with a protonated imine N atom, strong delocalization is also observed among the three C—N bonds, which are in the range of 1.31 (1)-1.34 (1) Å. Further protonated guanidine units show comparable N—C_gua– and N═C_gua geometries (Herres-Pawlis et al., 2005; Herres et al., 2005; Wittman, 1999; Peters et al., 2008, Galezowski et al., 1994, Raab et al., 2003).

The crystal packing exhibits N1—H···F6(-x + 1, -y + 1, -z + 1) intermolecular interaction from cation to anion with H···F = 2.127 Å.

Related literature top

For synthesis, see: Herres-Pawlis et al. (2005). For related structures, see: Flörke et al. (2006); Neuba et al. (2007c); Pruszynski et al. (1992). For related literature, see: Börner et al. (2007, 2009); Galezowski et al. (1994); Harmjanz (1997); Herres et al. (2005); Herres-Pawlis et al. (2009); Neuba (2009); Neuba et al. (2007a,b, 2008a,b, 2010, 2011); Peters et al. (2008); Pohl et al. (2000); Raab et al. (2003); Schneider (2000); Waden (1999); Wittman (1999); Wittmann et al. (2001).

Experimental top

Preparation of the title compound: 1,1,3,3-Tetramethyl-2-[2-(tritylsulfanyl)-ethyl]guanidine (C₂₆H₃₁N₃) (417 mg, 1 mmol) was added to a solution of [Cu(MeCN)₄]PF₆ (373 mg, 1 mmol) in acetonitrile (aqueous, 15 ml); the mixture was stirred for 15 min at room temperature and then refluxed for further 15 min and filtered off. Colourless crystals were obtained using the vapour pressure equalization method with this solution in the presence of diethylether.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

Fig. 1. Molecular structure with displacement ellipsoids drawn at the 50% probability level. H atoms omitted for clarity.

N-[Bis(dimethylamino)methylidene]- 2-[(triphenylmethyl)sulfanyl]ethanaminium hexafluorophosphate top

Crystal data top

C₂₆H₃₂N₃S⁺·PF₆⁻	Z = 2
M_r = 563.58	F(000) = 588
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0111 (14) Å	Cell parameters from 786 reflections
b = 9.1376 (15) Å	θ = 2.4–27.9°
c = 17.564 (3) Å	µ = 0.25 mm⁻¹
α = 96.532 (3)°	T = 120 K
β = 100.225 (4)°	Block, colourless
γ = 108.053 (3)°	0.33 × 0.30 × 0.26 mm
V = 1331.0 (4) Å³

Data collection top

Bruker SMART APEX diffractometer	6281 independent reflections
Radiation source: sealed tube	4547 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→10
T_min = 0.924, T_max = 0.939	k = −12→11
11922 measured reflections	l = −23→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.104	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0445P)²] where P = (F_o² + 2F_c²)/3
6281 reflections	(Δ/σ)_max < 0.001
338 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₆H₃₂N₃S⁺·PF₆⁻	γ = 108.053 (3)°
M_r = 563.58	V = 1331.0 (4) Å³
Triclinic, P1	Z = 2
a = 9.0111 (14) Å	Mo Kα radiation
b = 9.1376 (15) Å	µ = 0.25 mm⁻¹
c = 17.564 (3) Å	T = 120 K
α = 96.532 (3)°	0.33 × 0.30 × 0.26 mm
β = 100.225 (4)°

Data collection top

Bruker SMART APEX diffractometer	6281 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4547 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.939	R_int = 0.060
11922 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 0.96	Δρ_max = 0.38 e Å⁻³
6281 reflections	Δρ_min = −0.42 e Å⁻³
338 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 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

	x	y	z	U_iso*/U_eq
S1	0.77994 (6)	0.61888 (5)	0.29140 (3)	0.02002 (12)
N1	0.6327 (2)	0.89606 (18)	0.43688 (9)	0.0242 (4)
H1A	0.6289	0.8850	0.4857	0.029*
N2	0.7383 (2)	1.16512 (18)	0.47245 (9)	0.0253 (4)
N3	0.5695 (2)	1.05179 (18)	0.34970 (9)	0.0252 (4)
C1	0.6470 (2)	1.0380 (2)	0.41911 (10)	0.0211 (4)
C2	0.7029 (3)	1.3121 (2)	0.47981 (13)	0.0378 (6)
H2A	0.7840	1.3922	0.4625	0.057*
H2B	0.7042	1.3471	0.5348	0.057*
H2C	0.5969	1.2948	0.4470	0.057*
C3	0.8710 (3)	1.1626 (3)	0.53285 (12)	0.0338 (5)
H3A	0.8341	1.1432	0.5812	0.051*
H3B	0.9578	1.2636	0.5434	0.051*
H3C	0.9102	1.0792	0.5145	0.051*
C4	0.6343 (3)	1.1837 (3)	0.31065 (13)	0.0407 (6)
H4A	0.5737	1.2556	0.3145	0.061*
H4B	0.6252	1.1443	0.2551	0.061*
H4C	0.7473	1.2390	0.3362	0.061*
C5	0.4191 (3)	0.9342 (3)	0.30549 (12)	0.0350 (5)
H5A	0.4396	0.8717	0.2619	0.052*
H5B	0.3447	0.9862	0.2845	0.052*
H5C	0.3720	0.8657	0.3403	0.052*
C6	0.6227 (2)	0.7568 (2)	0.38190 (11)	0.0245 (4)
H6A	0.5129	0.7109	0.3485	0.029*
H6B	0.6430	0.6775	0.4124	0.029*
C7	0.7419 (2)	0.7943 (2)	0.32952 (11)	0.0207 (4)
H7A	0.8437	0.8738	0.3601	0.025*
H7B	0.6989	0.8384	0.2852	0.025*
C8	0.7037 (2)	0.5855 (2)	0.18294 (10)	0.0173 (4)
C11	0.6980 (2)	0.4160 (2)	0.15696 (10)	0.0177 (4)
C12	0.8390 (2)	0.3816 (2)	0.17641 (11)	0.0226 (4)
H12A	0.9333	0.4611	0.2068	0.027*
C13	0.8442 (2)	0.2340 (2)	0.15229 (12)	0.0269 (4)
H13A	0.9412	0.2127	0.1664	0.032*
C14	0.7079 (3)	0.1177 (2)	0.10767 (11)	0.0270 (5)
H14A	0.7109	0.0164	0.0906	0.032*
C15	0.5672 (3)	0.1497 (2)	0.08807 (11)	0.0266 (4)
H15A	0.4732	0.0697	0.0578	0.032*
C16	0.5622 (2)	0.2984 (2)	0.11234 (11)	0.0220 (4)
H16A	0.4649	0.3192	0.0982	0.026*
C21	0.5359 (2)	0.5994 (2)	0.16573 (10)	0.0172 (4)
C22	0.4204 (2)	0.5180 (2)	0.20308 (10)	0.0206 (4)
H22A	0.4475	0.4567	0.2399	0.025*
C23	0.2669 (2)	0.5248 (2)	0.18760 (11)	0.0230 (4)
H23A	0.1900	0.4685	0.2138	0.028*
C24	0.2246 (2)	0.6135 (2)	0.13396 (11)	0.0237 (4)
H24A	0.1192	0.6181	0.1233	0.028*
C25	0.3372 (2)	0.6948 (2)	0.09638 (11)	0.0235 (4)
H25A	0.3092	0.7558	0.0596	0.028*
C26	0.4920 (2)	0.6881 (2)	0.11204 (11)	0.0208 (4)
H26A	0.5686	0.7448	0.0858	0.025*
C31	0.8208 (2)	0.6940 (2)	0.14281 (10)	0.0183 (4)
C32	0.8071 (2)	0.6503 (2)	0.06202 (11)	0.0231 (4)
H32A	0.7257	0.5565	0.0338	0.028*
C33	0.9100 (2)	0.7415 (2)	0.02285 (11)	0.0268 (4)
H33A	0.8989	0.7100	−0.0319	0.032*
C34	1.0294 (2)	0.8785 (2)	0.06290 (12)	0.0259 (4)
H34A	1.1011	0.9406	0.0361	0.031*
C35	1.0432 (2)	0.9240 (2)	0.14238 (12)	0.0252 (4)
H35A	1.1240	1.0185	0.1701	0.030*
C36	0.9401 (2)	0.8329 (2)	0.18186 (11)	0.0216 (4)
H36A	0.9512	0.8658	0.2365	0.026*
P1	0.19146 (7)	0.27386 (6)	0.37421 (3)	0.02543 (13)
F1	0.02793 (18)	0.13314 (18)	0.35865 (10)	0.0699 (5)
F2	0.20703 (19)	0.22909 (16)	0.28687 (7)	0.0526 (4)
F3	0.35707 (17)	0.41217 (16)	0.39103 (9)	0.0547 (4)
F4	0.10033 (18)	0.38923 (16)	0.34893 (8)	0.0531 (4)
F5	0.18070 (19)	0.31694 (17)	0.46304 (8)	0.0524 (4)
F6	0.28644 (18)	0.15713 (16)	0.40077 (7)	0.0472 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0229 (3)	0.0197 (2)	0.0182 (2)	0.0101 (2)	0.00173 (19)	0.00234 (17)
N1	0.0361 (10)	0.0218 (8)	0.0170 (8)	0.0095 (8)	0.0118 (7)	0.0047 (6)
N2	0.0275 (10)	0.0227 (8)	0.0245 (9)	0.0083 (7)	0.0052 (7)	0.0003 (7)
N3	0.0312 (10)	0.0246 (9)	0.0219 (8)	0.0126 (8)	0.0058 (7)	0.0043 (7)
C1	0.0222 (11)	0.0251 (10)	0.0198 (9)	0.0107 (8)	0.0100 (8)	0.0032 (8)
C2	0.0447 (15)	0.0216 (11)	0.0446 (14)	0.0110 (10)	0.0088 (11)	−0.0019 (9)
C3	0.0299 (12)	0.0375 (12)	0.0279 (11)	0.0083 (10)	0.0006 (10)	−0.0007 (9)
C4	0.0584 (17)	0.0377 (13)	0.0347 (12)	0.0214 (12)	0.0157 (12)	0.0186 (10)
C5	0.0346 (13)	0.0395 (13)	0.0291 (11)	0.0195 (11)	−0.0029 (10)	−0.0047 (9)
C6	0.0339 (12)	0.0191 (9)	0.0225 (10)	0.0103 (9)	0.0093 (9)	0.0031 (7)
C7	0.0222 (10)	0.0161 (9)	0.0232 (10)	0.0066 (8)	0.0045 (8)	0.0026 (7)
C8	0.0179 (10)	0.0160 (9)	0.0159 (9)	0.0045 (8)	0.0018 (7)	0.0019 (7)
C11	0.0207 (10)	0.0170 (9)	0.0168 (9)	0.0068 (8)	0.0064 (8)	0.0045 (7)
C12	0.0195 (10)	0.0198 (9)	0.0273 (10)	0.0057 (8)	0.0054 (8)	0.0022 (8)
C13	0.0281 (12)	0.0250 (10)	0.0328 (11)	0.0137 (9)	0.0100 (9)	0.0067 (8)
C14	0.0374 (13)	0.0169 (9)	0.0292 (11)	0.0108 (9)	0.0122 (10)	0.0018 (8)
C15	0.0295 (12)	0.0208 (10)	0.0234 (10)	0.0012 (9)	0.0066 (9)	−0.0008 (8)
C16	0.0215 (11)	0.0224 (10)	0.0204 (9)	0.0069 (8)	0.0026 (8)	0.0020 (7)
C21	0.0168 (10)	0.0149 (8)	0.0173 (9)	0.0054 (7)	−0.0001 (7)	−0.0014 (7)
C22	0.0227 (11)	0.0200 (9)	0.0211 (10)	0.0091 (8)	0.0044 (8)	0.0065 (7)
C23	0.0192 (10)	0.0227 (10)	0.0270 (10)	0.0055 (8)	0.0068 (8)	0.0061 (8)
C24	0.0173 (10)	0.0258 (10)	0.0287 (11)	0.0100 (8)	0.0033 (8)	0.0033 (8)
C25	0.0248 (11)	0.0229 (10)	0.0250 (10)	0.0115 (9)	0.0029 (9)	0.0077 (8)
C26	0.0210 (10)	0.0191 (9)	0.0230 (10)	0.0070 (8)	0.0052 (8)	0.0057 (7)
C31	0.0173 (10)	0.0179 (9)	0.0228 (9)	0.0094 (8)	0.0046 (8)	0.0052 (7)
C32	0.0210 (10)	0.0216 (9)	0.0246 (10)	0.0057 (8)	0.0023 (8)	0.0044 (8)
C33	0.0290 (12)	0.0313 (11)	0.0226 (10)	0.0114 (10)	0.0068 (9)	0.0098 (8)
C34	0.0246 (11)	0.0262 (10)	0.0336 (11)	0.0122 (9)	0.0110 (9)	0.0155 (9)
C35	0.0190 (10)	0.0175 (9)	0.0375 (12)	0.0047 (8)	0.0041 (9)	0.0061 (8)
C36	0.0197 (10)	0.0200 (9)	0.0253 (10)	0.0078 (8)	0.0044 (8)	0.0033 (8)
P1	0.0307 (3)	0.0207 (3)	0.0231 (3)	0.0066 (2)	0.0047 (2)	0.0047 (2)
F1	0.0451 (10)	0.0428 (9)	0.0994 (13)	−0.0102 (7)	0.0113 (9)	0.0027 (9)
F2	0.0916 (12)	0.0495 (9)	0.0248 (7)	0.0340 (9)	0.0148 (7)	0.0079 (6)
F3	0.0403 (9)	0.0380 (8)	0.0720 (10)	−0.0026 (7)	0.0121 (8)	0.0015 (7)
F4	0.0661 (11)	0.0509 (9)	0.0512 (9)	0.0377 (8)	0.0019 (8)	0.0112 (7)
F5	0.0803 (11)	0.0580 (9)	0.0337 (7)	0.0362 (9)	0.0256 (7)	0.0098 (6)
F6	0.0765 (11)	0.0483 (8)	0.0350 (7)	0.0411 (8)	0.0162 (7)	0.0173 (6)

Geometric parameters (Å, º) top

S1—C7	1.8202 (17)	C13—C14	1.383 (3)
S1—C8	1.8620 (18)	C13—H13A	0.9500
N1—C1	1.341 (2)	C14—C15	1.381 (3)
N1—C6	1.476 (2)	C14—H14A	0.9500
N1—H1A	0.8800	C15—C16	1.394 (2)
N2—C1	1.338 (2)	C15—H15A	0.9500
N2—C3	1.459 (3)	C16—H16A	0.9500
N2—C2	1.470 (2)	C21—C22	1.393 (3)
N3—C1	1.333 (2)	C21—C26	1.394 (2)
N3—C5	1.459 (3)	C22—C23	1.384 (3)
N3—C4	1.469 (3)	C22—H22A	0.9500
C2—H2A	0.9800	C23—C24	1.388 (3)
C2—H2B	0.9800	C23—H23A	0.9500
C2—H2C	0.9800	C24—C25	1.378 (3)
C3—H3A	0.9800	C24—H24A	0.9500
C3—H3B	0.9800	C25—C26	1.395 (3)
C3—H3C	0.9800	C25—H25A	0.9500
C4—H4A	0.9800	C26—H26A	0.9500
C4—H4B	0.9800	C31—C36	1.390 (2)
C4—H4C	0.9800	C31—C32	1.402 (2)
C5—H5A	0.9800	C32—C33	1.381 (3)
C5—H5B	0.9800	C32—H32A	0.9500
C5—H5C	0.9800	C33—C34	1.384 (3)
C6—C7	1.521 (3)	C33—H33A	0.9500
C6—H6A	0.9900	C34—C35	1.383 (3)
C6—H6B	0.9900	C34—H34A	0.9500
C7—H7A	0.9900	C35—C36	1.385 (3)
C7—H7B	0.9900	C35—H35A	0.9500
C8—C21	1.537 (2)	C36—H36A	0.9500
C8—C31	1.538 (2)	P1—F4	1.5801 (13)
C8—C11	1.546 (2)	P1—F3	1.5814 (14)
C11—C16	1.386 (3)	P1—F1	1.5819 (15)
C11—C12	1.396 (3)	P1—F2	1.5842 (13)
C12—C13	1.385 (2)	P1—F5	1.5924 (13)
C12—H12A	0.9500	P1—F6	1.6202 (13)

C7—S1—C8	105.13 (8)	C14—C13—H13A	120.1
C1—N1—C6	125.84 (15)	C12—C13—H13A	120.1
C1—N1—H1A	117.1	C15—C14—C13	119.59 (17)
C6—N1—H1A	117.1	C15—C14—H14A	120.2
C1—N2—C3	122.00 (16)	C13—C14—H14A	120.2
C1—N2—C2	122.76 (17)	C14—C15—C16	120.53 (18)
C3—N2—C2	114.95 (16)	C14—C15—H15A	119.7
C1—N3—C5	122.70 (17)	C16—C15—H15A	119.7
C1—N3—C4	121.96 (18)	C11—C16—C15	120.46 (18)
C5—N3—C4	115.28 (17)	C11—C16—H16A	119.8
N3—C1—N2	120.65 (17)	C15—C16—H16A	119.8
N3—C1—N1	120.34 (17)	C22—C21—C26	117.89 (17)
N2—C1—N1	119.01 (17)	C22—C21—C8	119.67 (15)
N2—C2—H2A	109.5	C26—C21—C8	122.42 (17)
N2—C2—H2B	109.5	C23—C22—C21	121.25 (17)
H2A—C2—H2B	109.5	C23—C22—H22A	119.4
N2—C2—H2C	109.5	C21—C22—H22A	119.4
H2A—C2—H2C	109.5	C22—C23—C24	120.33 (18)
H2B—C2—H2C	109.5	C22—C23—H23A	119.8
N2—C3—H3A	109.5	C24—C23—H23A	119.8
N2—C3—H3B	109.5	C25—C24—C23	119.29 (18)
H3A—C3—H3B	109.5	C25—C24—H24A	120.4
N2—C3—H3C	109.5	C23—C24—H24A	120.4
H3A—C3—H3C	109.5	C24—C25—C26	120.40 (17)
H3B—C3—H3C	109.5	C24—C25—H25A	119.8
N3—C4—H4A	109.5	C26—C25—H25A	119.8
N3—C4—H4B	109.5	C21—C26—C25	120.84 (18)
H4A—C4—H4B	109.5	C21—C26—H26A	119.6
N3—C4—H4C	109.5	C25—C26—H26A	119.6
H4A—C4—H4C	109.5	C36—C31—C32	117.81 (17)
H4B—C4—H4C	109.5	C36—C31—C8	123.97 (16)
N3—C5—H5A	109.5	C32—C31—C8	118.22 (16)
N3—C5—H5B	109.5	C33—C32—C31	121.00 (18)
H5A—C5—H5B	109.5	C33—C32—H32A	119.5
N3—C5—H5C	109.5	C31—C32—H32A	119.5
H5A—C5—H5C	109.5	C32—C33—C34	120.39 (18)
H5B—C5—H5C	109.5	C32—C33—H33A	119.8
N1—C6—C7	112.59 (15)	C34—C33—H33A	119.8
N1—C6—H6A	109.1	C35—C34—C33	119.25 (18)
C7—C6—H6A	109.1	C35—C34—H34A	120.4
N1—C6—H6B	109.1	C33—C34—H34A	120.4
C7—C6—H6B	109.1	C34—C35—C36	120.53 (18)
H6A—C6—H6B	107.8	C34—C35—H35A	119.7
C6—C7—S1	110.58 (12)	C36—C35—H35A	119.7
C6—C7—H7A	109.5	C35—C36—C31	121.02 (18)
S1—C7—H7A	109.5	C35—C36—H36A	119.5
C6—C7—H7B	109.5	C31—C36—H36A	119.5
S1—C7—H7B	109.5	F4—P1—F3	90.03 (8)
H7A—C7—H7B	108.1	F4—P1—F1	91.33 (9)
C21—C8—C31	112.93 (14)	F3—P1—F1	178.58 (9)
C21—C8—C11	111.65 (14)	F4—P1—F2	91.47 (8)
C31—C8—C11	108.14 (14)	F3—P1—F2	89.85 (8)
C21—C8—S1	108.93 (12)	F1—P1—F2	90.54 (9)
C31—C8—S1	112.31 (12)	F4—P1—F5	90.31 (8)
C11—C8—S1	102.41 (11)	F3—P1—F5	89.46 (8)
C16—C11—C12	118.30 (16)	F1—P1—F5	90.11 (9)
C16—C11—C8	123.45 (16)	F2—P1—F5	178.08 (8)
C12—C11—C8	118.19 (16)	F4—P1—F6	179.38 (9)
C13—C12—C11	121.31 (18)	F3—P1—F6	89.43 (8)
C13—C12—H12A	119.3	F1—P1—F6	89.21 (9)
C11—C12—H12A	119.3	F2—P1—F6	88.82 (7)
C14—C13—C12	119.82 (18)	F5—P1—F6	89.39 (7)

C5—N3—C1—N2	−150.95 (18)	C14—C15—C16—C11	−0.4 (3)
C4—N3—C1—N2	32.1 (3)	C31—C8—C21—C22	−174.76 (15)
C5—N3—C1—N1	28.1 (3)	C11—C8—C21—C22	63.1 (2)
C4—N3—C1—N1	−148.85 (18)	S1—C8—C21—C22	−49.25 (19)
C3—N2—C1—N3	−154.99 (18)	C31—C8—C21—C26	6.9 (2)
C2—N2—C1—N3	31.5 (3)	C11—C8—C21—C26	−115.21 (18)
C3—N2—C1—N1	25.9 (3)	S1—C8—C21—C26	132.42 (15)
C2—N2—C1—N1	−147.63 (19)	C26—C21—C22—C23	0.0 (3)
C6—N1—C1—N3	37.8 (3)	C8—C21—C22—C23	−178.44 (16)
C6—N1—C1—N2	−143.12 (19)	C21—C22—C23—C24	0.1 (3)
C1—N1—C6—C7	43.2 (3)	C22—C23—C24—C25	−0.1 (3)
N1—C6—C7—S1	158.36 (13)	C23—C24—C25—C26	0.0 (3)
C8—S1—C7—C6	115.92 (14)	C22—C21—C26—C25	0.0 (3)
C7—S1—C8—C21	−47.42 (14)	C8—C21—C26—C25	178.32 (16)
C7—S1—C8—C31	78.45 (13)	C24—C25—C26—C21	0.1 (3)
C7—S1—C8—C11	−165.77 (12)	C21—C8—C31—C36	103.47 (19)
C21—C8—C11—C16	9.8 (2)	C11—C8—C31—C36	−132.46 (17)
C31—C8—C11—C16	−115.03 (19)	S1—C8—C31—C36	−20.2 (2)
S1—C8—C11—C16	126.21 (16)	C21—C8—C31—C32	−76.83 (19)
C21—C8—C11—C12	−173.28 (15)	C11—C8—C31—C32	47.2 (2)
C31—C8—C11—C12	61.9 (2)	S1—C8—C31—C32	159.51 (14)
S1—C8—C11—C12	−56.87 (18)	C36—C31—C32—C33	0.7 (3)
C16—C11—C12—C13	−0.3 (3)	C8—C31—C32—C33	−179.02 (16)
C8—C11—C12—C13	−177.34 (17)	C31—C32—C33—C34	0.1 (3)
C11—C12—C13—C14	0.4 (3)	C32—C33—C34—C35	−0.8 (3)
C12—C13—C14—C15	−0.5 (3)	C33—C34—C35—C36	0.8 (3)
C13—C14—C15—C16	0.5 (3)	C34—C35—C36—C31	0.0 (3)
C12—C11—C16—C15	0.3 (3)	C32—C31—C36—C35	−0.7 (3)
C8—C11—C16—C15	177.21 (17)	C8—C31—C36—C35	178.97 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F6ⁱ	0.88	2.13	2.949 (2)	155

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₂N₃S⁺·PF₆⁻
M_r	563.58
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	9.0111 (14), 9.1376 (15), 17.564 (3)
α, β, γ (°)	96.532 (3), 100.225 (4), 108.053 (3)
V (Å³)	1331.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.33 × 0.30 × 0.26

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.924, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	11922, 6281, 4547
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.104, 0.96
No. of reflections	6281
No. of parameters	338
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.42

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F6ⁱ	0.8800	2.1300	2.949 (2)	155.00

Symmetry code: (i) −x+1, −y+1, −z+1.

References

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1238-o1239

doi:10.1107/S1600536811014929

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[Bis(di­methyl­amino)­methyl­­idene]-2-[(tri­phenyl­meth­yl)sulfan­yl]ethanaminium hexa­fluoro­phosphate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N-[Bis(dimethylamino)methylidene]-2-[(triphenylmethyl)sulfanyl]ethanaminium hexafluorophosphate