Crystal structure of 1-hy­droxy-2,2,6,6-tetra­methyl­piperidin-1-ium tri­fluoro­methane­sulfonate

Godemann, C.; Spannenberg, A.; Beweries, T.

doi:10.1107/S2056989015020897

organic compounds

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Volume 71| Part 12| December 2015| Page o921

https://doi.org/10.1107/S2056989015020897

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Crystal structure of 1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium trifluoromethanesulfonate

Christian Godemann,^a Anke Spannenberg ^a and Torsten Beweries ^a ^*

^aLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
^*Correspondence e-mail: torsten.beweries@catalysis.de

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 26 October 2015; accepted 4 November 2015; online 7 November 2015)

In the cation of the title salt, C₉H₂₀NO⁺·CF₃O₃S⁻, the six-membered heterocyclic ring displays a chair conformation. In the crystal, centrosymmetric pairs of cations and anions are linked by N—H⋯O and O—H⋯O hydrogen bonds to form rings with a R₄⁴(14) graph-set motif.

Keywords: crystal structure; TEMPO; ammonium salt; triflate; hydrogen bonding.

CCDC reference: 1435030

1. Related literature

For molecular structures and discussions of related compounds, see: Jaitner & Wurst (1997 ); Spirk et al. (2010 ); Ananchenko et al. (2006 ); Percino et al. (2016 ). For the molecular structure of the neutral TEMPO-H compound, see: Mader et al. (2007 ); Giffin et al. (2011 ).

2. Experimental

2.1. Crystal data

C₉H₂₀NO⁺·CF₃O₃S⁻
M_r = 307.33
Triclinic, $[P \overline 1]$
a = 8.2824 (2) Å
b = 8.7656 (2) Å
c = 10.5703 (3) Å
α = 79.5417 (7)°
β = 76.5159 (7)°
γ = 75.5022 (6)°
V = 716.28 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 150 K
0.55 × 0.38 × 0.34 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.83, T_max = 0.86
22933 measured reflections
3452 independent reflections
3039 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.05
3452 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4	0.84 (2)	1.78 (2)	2.6163 (14)	177 (2)
N1—H1B⋯O3ⁱ	0.875 (16)	1.991 (16)	2.8385 (14)	163.0 (14)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1435030

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015020897/rz5176sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020897/rz5176Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015020897/rz5176Isup3.cml

checkCIF report

Synthesis and crystallization top

An equimolar mixture of the titanocene(IV) triflate complex [(SiMe₂C₅Me₄)₂Ti(H₂O)(OH)(OTf)] (Godemann & Beweries, unpublished results) and 2,2,6,6-tetramethyl-1-hydroxypiperidine (TEMPO-H) in toluene was cooled to -78°C. After two weeks, the formation of colourless crystals of the title compound could be observed on slow evaporation of the solvent. Alternatively, layering a toluene solution of the same titanocene compound and TEMPO-H with n-hexane also resulted in the formation of colourless crystals of the title compound.

Refinement top

The H1A and H1B atoms were found from a difference Fourier map and refined freely. All other H atoms were placed in idealized positions with d(C—H) = 0.99 Å (CH₂), 0.98 Å (CH₃) and refined using a riding model with U_iso(H) fixed at 1.2 U_eq(C) for CH₂ and 1.5 U_eq(C) for CH₃. A rotating model was used for the methyl groups.

Related literature top

For molecular structures and discussions of related compounds, see: Jaitner & Wurst (1997); Spirk et al. (2010); Ananchenko et al. (2006); Percino et al. (2016). For the molecular structure of the neutral TEMPO-H compound, see: Mader et al. (2007); Giffin et al. (2011).

Structure description top

For molecular structures and discussions of related compounds, see: Jaitner & Wurst (1997); Spirk et al. (2010); Ananchenko et al. (2006); Percino et al. (2016). For the molecular structure of the neutral TEMPO-H compound, see: Mader et al. (2007); Giffin et al. (2011).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The hydrogen-bonding network (dashed lines) linking centrosymmetric pairs of cations and anions in the title compound. C-bound hydrogen atoms are omitted for clarity. Displacement ellipsoids are drawn at the 30% probability level.

1-Hydroxy-2,2,6,6-tetramethylpiperidin-1-ium trifluoromethanesulfonate top

Crystal data top

C₉H₂₀NO⁺·CF₃O₃S⁻	Z = 2
M_r = 307.33	F(000) = 324
Triclinic, P1	D_x = 1.425 Mg m⁻³
a = 8.2824 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7656 (2) Å	Cell parameters from 9968 reflections
c = 10.5703 (3) Å	θ = 2.6–28.9°
α = 79.5417 (7)°	µ = 0.27 mm⁻¹
β = 76.5159 (7)°	T = 150 K
γ = 75.5022 (6)°	Prism, colourless
V = 716.28 (3) Å³	0.55 × 0.38 × 0.34 mm

Data collection top

Bruker APEXII CCD diffractometer	3452 independent reflections
Radiation source: fine-focus sealed tube	3039 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	R_int = 0.020
φ and ω scans	θ_max = 28.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
T_min = 0.83, T_max = 0.86	k = −11→11
22933 measured reflections	l = −13→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0476P)² + 0.2597P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3452 reflections	Δρ_max = 0.32 e Å⁻³
184 parameters	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₉H₂₀NO⁺·CF₃O₃S⁻	γ = 75.5022 (6)°
M_r = 307.33	V = 716.28 (3) Å³
Triclinic, P1	Z = 2
a = 8.2824 (2) Å	Mo Kα radiation
b = 8.7656 (2) Å	µ = 0.27 mm⁻¹
c = 10.5703 (3) Å	T = 150 K
α = 79.5417 (7)°	0.55 × 0.38 × 0.34 mm
β = 76.5159 (7)°

Data collection top

Bruker APEXII CCD diffractometer	3452 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	3039 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.86	R_int = 0.020
22933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.32 e Å⁻³
3452 reflections	Δρ_min = −0.28 e Å⁻³
184 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.96872 (15)	0.80108 (15)	0.28534 (12)	0.0251 (3)
C2	0.96590 (19)	0.86192 (17)	0.14106 (13)	0.0371 (3)
H2A	0.8640	0.9487	0.1352	0.045*
H2B	1.0673	0.9072	0.1019	0.045*
C3	0.9637 (2)	0.7356 (2)	0.06137 (14)	0.0503 (5)
H3A	1.0691	0.6517	0.0611	0.060*
H3B	0.9595	0.7834	−0.0305	0.060*
C4	0.8101 (2)	0.66311 (19)	0.11958 (15)	0.0456 (4)
H4A	0.8100	0.5820	0.0655	0.055*
H4B	0.7057	0.7472	0.1151	0.055*
C5	0.80421 (17)	0.58576 (15)	0.26184 (13)	0.0287 (3)
C6	1.13968 (18)	0.69450 (19)	0.30494 (17)	0.0396 (3)
H6A	1.2234	0.7600	0.2937	0.059*
H6B	1.1782	0.6194	0.2402	0.059*
H6C	1.1273	0.6356	0.3936	0.059*
C7	0.92379 (19)	0.93950 (17)	0.36579 (16)	0.0360 (3)
H7A	0.9328	0.8983	0.4571	0.054*
H7B	0.8072	0.9985	0.3625	0.054*
H7C	1.0026	1.0105	0.3294	0.054*
C8	0.6305 (2)	0.5497 (2)	0.3250 (2)	0.0511 (5)
H8A	0.6018	0.4827	0.2724	0.077*
H8B	0.5446	0.6494	0.3293	0.077*
H8C	0.6334	0.4938	0.4138	0.077*
C9	0.94213 (19)	0.43502 (16)	0.27559 (15)	0.0343 (3)
H9A	0.9560	0.4085	0.3671	0.051*
H9B	1.0498	0.4523	0.2192	0.051*
H9C	0.9093	0.3473	0.2493	0.051*
C10	0.48030 (17)	0.77783 (16)	0.86989 (13)	0.0301 (3)
F1	0.32733 (11)	0.76163 (11)	0.86237 (9)	0.0403 (2)
F2	0.57731 (13)	0.63247 (11)	0.88758 (10)	0.0488 (3)
F3	0.46049 (15)	0.84651 (13)	0.97606 (9)	0.0522 (3)
N1	0.82282 (12)	0.71302 (11)	0.33670 (9)	0.0180 (2)
O1	0.82554 (13)	0.64554 (11)	0.46877 (8)	0.0285 (2)
O2	0.74038 (13)	0.88719 (14)	0.74267 (14)	0.0495 (3)
O3	0.45998 (13)	1.04716 (11)	0.72367 (10)	0.0352 (2)
O4	0.56749 (14)	0.80767 (14)	0.61969 (10)	0.0425 (3)
S1	0.57433 (4)	0.89340 (4)	0.72262 (3)	0.02752 (10)
H1A	0.745 (3)	0.700 (2)	0.516 (2)	0.050 (5)*
H1B	0.730 (2)	0.7873 (18)	0.3356 (15)	0.025 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0187 (6)	0.0249 (6)	0.0285 (6)	−0.0058 (4)	−0.0015 (5)	0.0019 (5)
C2	0.0327 (7)	0.0331 (7)	0.0270 (6)	0.0054 (6)	0.0074 (5)	0.0086 (5)
C3	0.0644 (11)	0.0464 (9)	0.0167 (6)	0.0215 (8)	0.0011 (6)	−0.0030 (6)
C4	0.0617 (10)	0.0393 (8)	0.0359 (8)	0.0188 (7)	−0.0286 (7)	−0.0221 (6)
C5	0.0290 (6)	0.0228 (6)	0.0368 (7)	0.0021 (5)	−0.0114 (5)	−0.0145 (5)
C6	0.0203 (6)	0.0402 (8)	0.0531 (9)	−0.0038 (6)	−0.0086 (6)	0.0050 (7)
C7	0.0354 (7)	0.0303 (7)	0.0484 (8)	−0.0133 (6)	−0.0121 (6)	−0.0068 (6)
C8	0.0323 (8)	0.0330 (8)	0.0957 (15)	−0.0088 (6)	−0.0148 (8)	−0.0230 (8)
C9	0.0393 (8)	0.0223 (6)	0.0381 (7)	0.0055 (5)	−0.0090 (6)	−0.0112 (5)
C10	0.0286 (7)	0.0293 (6)	0.0315 (7)	−0.0007 (5)	−0.0078 (5)	−0.0068 (5)
F1	0.0280 (4)	0.0431 (5)	0.0489 (5)	−0.0120 (4)	0.0008 (4)	−0.0084 (4)
F2	0.0473 (6)	0.0309 (5)	0.0588 (6)	0.0034 (4)	−0.0127 (4)	0.0043 (4)
F3	0.0693 (7)	0.0580 (6)	0.0319 (5)	−0.0098 (5)	−0.0128 (4)	−0.0148 (4)
N1	0.0177 (5)	0.0180 (4)	0.0160 (4)	−0.0009 (4)	−0.0013 (3)	−0.0031 (3)
O1	0.0368 (5)	0.0252 (4)	0.0151 (4)	0.0002 (4)	0.0018 (4)	−0.0004 (3)
O2	0.0206 (5)	0.0412 (6)	0.0850 (9)	−0.0062 (4)	−0.0104 (5)	−0.0052 (6)
O3	0.0290 (5)	0.0264 (5)	0.0432 (6)	0.0058 (4)	−0.0055 (4)	−0.0057 (4)
O4	0.0435 (6)	0.0459 (6)	0.0332 (5)	−0.0042 (5)	0.0055 (4)	−0.0172 (5)
S1	0.01852 (16)	0.02389 (17)	0.03577 (18)	0.00056 (11)	−0.00008 (12)	−0.00683 (12)

Geometric parameters (Å, º) top

C1—C6	1.5247 (18)	C7—H7A	0.9800
C1—C2	1.5251 (18)	C7—H7B	0.9800
C1—C7	1.5279 (19)	C7—H7C	0.9800
C1—N1	1.5362 (15)	C8—H8A	0.9800
C2—C3	1.514 (2)	C8—H8B	0.9800
C2—H2A	0.9900	C8—H8C	0.9800
C2—H2B	0.9900	C9—H9A	0.9800
C3—C4	1.516 (3)	C9—H9B	0.9800
C3—H3A	0.9900	C9—H9C	0.9800
C3—H3B	0.9900	C10—F3	1.3262 (16)
C4—C5	1.528 (2)	C10—F1	1.3314 (16)
C4—H4A	0.9900	C10—F2	1.3323 (16)
C4—H4B	0.9900	C10—S1	1.8202 (15)
C5—C8	1.522 (2)	N1—O1	1.4168 (12)
C5—C9	1.5244 (17)	N1—H1B	0.875 (16)
C5—N1	1.5354 (15)	O1—H1A	0.84 (2)
C6—H6A	0.9800	O2—S1	1.4260 (11)
C6—H6B	0.9800	O3—S1	1.4406 (9)
C6—H6C	0.9800	O4—S1	1.4486 (11)

C6—C1—C2	112.20 (11)	C1—C7—H7B	109.5
C6—C1—C7	110.16 (12)	H7A—C7—H7B	109.5
C2—C1—C7	110.70 (11)	C1—C7—H7C	109.5
C6—C1—N1	111.77 (10)	H7A—C7—H7C	109.5
C2—C1—N1	106.75 (11)	H7B—C7—H7C	109.5
C7—C1—N1	104.98 (10)	C5—C8—H8A	109.5
C3—C2—C1	113.88 (12)	C5—C8—H8B	109.5
C3—C2—H2A	108.8	H8A—C8—H8B	109.5
C1—C2—H2A	108.8	C5—C8—H8C	109.5
C3—C2—H2B	108.8	H8A—C8—H8C	109.5
C1—C2—H2B	108.8	H8B—C8—H8C	109.5
H2A—C2—H2B	107.7	C5—C9—H9A	109.5
C2—C3—C4	109.99 (11)	C5—C9—H9B	109.5
C2—C3—H3A	109.7	H9A—C9—H9B	109.5
C4—C3—H3A	109.7	C5—C9—H9C	109.5
C2—C3—H3B	109.7	H9A—C9—H9C	109.5
C4—C3—H3B	109.7	H9B—C9—H9C	109.5
H3A—C3—H3B	108.2	F3—C10—F1	107.06 (11)
C3—C4—C5	113.93 (13)	F3—C10—F2	108.19 (12)
C3—C4—H4A	108.8	F1—C10—F2	107.48 (11)
C5—C4—H4A	108.8	F3—C10—S1	111.63 (10)
C3—C4—H4B	108.8	F1—C10—S1	111.42 (9)
C5—C4—H4B	108.8	F2—C10—S1	110.87 (10)
H4A—C4—H4B	107.7	O1—N1—C5	108.32 (9)
C8—C5—C9	109.71 (12)	O1—N1—C1	109.24 (9)
C8—C5—C4	111.57 (14)	C5—N1—C1	120.28 (9)
C9—C5—C4	112.76 (11)	O1—N1—H1B	108.1 (10)
C8—C5—N1	105.18 (11)	C5—N1—H1B	105.5 (10)
C9—C5—N1	111.54 (10)	C1—N1—H1B	104.8 (10)
C4—C5—N1	105.78 (11)	N1—O1—H1A	107.7 (13)
C1—C6—H6A	109.5	O2—S1—O3	115.62 (7)
C1—C6—H6B	109.5	O2—S1—O4	115.69 (7)
H6A—C6—H6B	109.5	O3—S1—O4	113.73 (7)
C1—C6—H6C	109.5	O2—S1—C10	103.77 (7)
H6A—C6—H6C	109.5	O3—S1—C10	103.23 (6)
H6B—C6—H6C	109.5	O4—S1—C10	102.32 (7)
C1—C7—H7A	109.5

C6—C1—C2—C3	71.46 (16)	C2—C1—N1—O1	176.56 (9)
C7—C1—C2—C3	−165.02 (13)	C7—C1—N1—O1	−65.88 (12)
N1—C1—C2—C3	−51.30 (15)	C6—C1—N1—C5	−72.58 (14)
C1—C2—C3—C4	58.13 (16)	C2—C1—N1—C5	50.45 (13)
C2—C3—C4—C5	−59.31 (16)	C7—C1—N1—C5	168.01 (10)
C3—C4—C5—C8	166.79 (12)	F3—C10—S1—O2	65.11 (11)
C3—C4—C5—C9	−69.21 (15)	F1—C10—S1—O2	−175.25 (9)
C3—C4—C5—N1	52.95 (14)	F2—C10—S1—O2	−55.59 (12)
C8—C5—N1—O1	64.27 (13)	F3—C10—S1—O3	−55.88 (11)
C9—C5—N1—O1	−54.59 (13)	F1—C10—S1—O3	63.76 (10)
C4—C5—N1—O1	−177.53 (10)	F2—C10—S1—O3	−176.58 (10)
C8—C5—N1—C1	−169.19 (12)	F3—C10—S1—O4	−174.21 (10)
C9—C5—N1—C1	71.95 (14)	F1—C10—S1—O4	−54.57 (11)
C4—C5—N1—C1	−50.99 (14)	F2—C10—S1—O4	65.09 (11)
C6—C1—N1—O1	53.53 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4	0.84 (2)	1.78 (2)	2.6163 (14)	177 (2)
N1—H1B···O3ⁱ	0.875 (16)	1.991 (16)	2.8385 (14)	163.0 (14)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4	0.84 (2)	1.78 (2)	2.6163 (14)	177 (2)
N1—H1B···O3ⁱ	0.875 (16)	1.991 (16)	2.8385 (14)	163.0 (14)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

Financial support by the BMBF (project `Light2Hydrogen') is gratefully acknowledged.

References

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Volume 71| Part 12| December 2015| Page o921

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

Crystal structure of 1-hy­dr­oxy-2,2,6,6-tetra­methyl­piperidin-1-ium tri­fluoro­methane­sulfonate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium trifluoromethanesulfonate