N,N,2,4,6-Penta-methyl-anilinium hexa-fluoro-phosphate.

In the crystal structure of the title salt, C11H18N(+)·PF6(-), the cation and anion are connected via an N-H⋯F hydrogen bond; weak C-H⋯F hydrogen bonding also occurs between the cations and anions.

Related literature

For the background to the title salt, see: Haertling et al. (1999 ▶); Homes et al. (2001 ▶).

Experimental

Crystal data

C11H18N+·PF6 −

M = 309.23

Monoclinic,

a = 11.466 (2) Å

b = 8.2439 (16) Å

c = 15.559 (3) Å

β = 97.82 (3)°

V = 1457.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.20 × 0.19 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer

14679 measured reflections

3340 independent reflections

1942 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.186

S = 1.03

3340 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049379/xu5658sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049379/xu5658Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049379/xu5658Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H18N+·PF6−	F(000) = 640
Mr = 309.23	Dx = 1.410 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3340 reflections
a = 11.466 (2) Å	θ = 2.7–27.5°
b = 8.2439 (16) Å	µ = 0.24 mm−1
c = 15.559 (3) Å	T = 293 K
β = 97.82 (3)°	Prism, colorless
V = 1457.0 (5) Å3	0.20 × 0.19 × 0.18 mm
Z = 4

Rigaku Mercury2 diffractometer	1942 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 13.6612 pixels mm-1	h = −14→14
CCD_Profile_fitting scans	k = −10→10
14679 measured reflections	l = −20→20
3340 independent reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0788P)2 + 0.4571P] where P = (Fo2 + 2Fc2)/3
3340 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
P1	0.32971 (7)	0.80605 (11)	0.35021 (6)	0.0588 (3)
N1	0.68536 (19)	0.8547 (3)	0.37739 (14)	0.0466 (6)
H1	0.6213	0.8201	0.4009	0.056*
F1	0.43410 (18)	0.9123 (3)	0.39786 (18)	0.1138 (9)
F2	0.2284 (2)	0.6948 (3)	0.30436 (15)	0.0956 (8)
F3	0.3564 (2)	0.8663 (3)	0.25858 (15)	0.1075 (8)
F4	0.3043 (2)	0.7382 (4)	0.44062 (14)	0.1104 (9)
F5	0.4216 (2)	0.6632 (3)	0.34402 (15)	0.0948 (7)
F6	0.2418 (2)	0.9486 (3)	0.3564 (2)	0.1270 (11)
C1	0.7884 (2)	0.7941 (3)	0.43803 (17)	0.0432 (6)
C2	0.7626 (2)	0.7091 (3)	0.51013 (18)	0.0482 (7)
C3	0.8564 (3)	0.6512 (4)	0.56766 (19)	0.0559 (8)
H3	0.8409	0.5922	0.6158	0.067*
C4	0.9722 (3)	0.6782 (4)	0.5560 (2)	0.0560 (8)
C5	0.9930 (3)	0.7638 (4)	0.4838 (2)	0.0568 (8)
H5	1.0706	0.7832	0.4757	0.068*
C6	0.9034 (2)	0.8228 (3)	0.42212 (18)	0.0487 (7)
C7	1.0726 (3)	0.6148 (4)	0.6206 (2)	0.0763 (11)
H7A	1.1392	0.5919	0.5912	0.114*
H7B	1.0484	0.5172	0.6468	0.114*
H7C	1.0940	0.6949	0.6647	0.114*
C8	0.6383 (3)	0.6771 (5)	0.5279 (2)	0.0735 (10)
H8A	0.6403	0.6149	0.5802	0.110*
H8B	0.5964	0.6177	0.4803	0.110*
H8C	0.5991	0.7784	0.5344	0.110*
C9	0.9394 (3)	0.9078 (5)	0.3437 (2)	0.0707 (10)
H9A	0.9402	0.8312	0.2973	0.106*
H9B	1.0166	0.9534	0.3584	0.106*
H9C	0.8842	0.9928	0.3256	0.106*
C10	0.6719 (3)	0.7799 (5)	0.2888 (2)	0.0751 (10)
H10A	0.7327	0.8200	0.2576	0.113*
H10B	0.5963	0.8079	0.2580	0.113*
H10C	0.6783	0.6642	0.2940	0.113*
C11	0.6748 (3)	1.0353 (4)	0.3754 (2)	0.0693 (9)
H11A	0.6797	1.0758	0.4336	0.104*
H11B	0.6005	1.0656	0.3434	0.104*
H11C	0.7375	1.0806	0.3480	0.104*

	U11	U22	U33	U12	U13	U23
P1	0.0438 (5)	0.0666 (6)	0.0658 (6)	−0.0018 (4)	0.0060 (4)	−0.0077 (4)
N1	0.0410 (12)	0.0534 (14)	0.0461 (13)	−0.0011 (10)	0.0077 (10)	0.0047 (10)
F1	0.0631 (13)	0.121 (2)	0.154 (2)	−0.0277 (14)	0.0021 (14)	−0.0462 (17)
F2	0.0882 (15)	0.1006 (17)	0.0926 (16)	−0.0308 (13)	−0.0073 (12)	−0.0137 (12)
F3	0.126 (2)	0.1015 (18)	0.0994 (18)	0.0058 (15)	0.0303 (15)	0.0358 (14)
F4	0.1209 (19)	0.148 (2)	0.0674 (15)	−0.0243 (18)	0.0314 (13)	−0.0149 (14)
F5	0.0918 (15)	0.0934 (16)	0.1004 (17)	0.0358 (13)	0.0172 (13)	0.0080 (12)
F6	0.0688 (14)	0.0922 (18)	0.222 (3)	0.0201 (13)	0.0262 (16)	−0.0326 (19)
C1	0.0427 (14)	0.0416 (15)	0.0451 (15)	0.0000 (12)	0.0057 (11)	−0.0008 (12)
C2	0.0487 (15)	0.0503 (17)	0.0466 (16)	0.0005 (13)	0.0096 (12)	0.0003 (13)
C3	0.064 (2)	0.0586 (19)	0.0435 (16)	0.0016 (15)	0.0034 (14)	0.0015 (13)
C4	0.0576 (18)	0.0516 (18)	0.0548 (18)	0.0065 (14)	−0.0069 (14)	−0.0121 (14)
C5	0.0431 (15)	0.0622 (19)	0.065 (2)	−0.0031 (14)	0.0062 (14)	−0.0076 (16)
C6	0.0448 (15)	0.0517 (17)	0.0504 (17)	−0.0029 (13)	0.0092 (12)	−0.0023 (13)
C7	0.076 (2)	0.074 (2)	0.070 (2)	0.0143 (19)	−0.0217 (18)	−0.0071 (18)
C8	0.059 (2)	0.096 (3)	0.068 (2)	−0.0054 (18)	0.0193 (16)	0.0252 (19)
C9	0.0540 (18)	0.086 (2)	0.076 (2)	−0.0051 (18)	0.0245 (16)	0.0151 (19)
C10	0.067 (2)	0.105 (3)	0.051 (2)	−0.005 (2)	−0.0001 (15)	−0.0204 (18)
C11	0.069 (2)	0.060 (2)	0.079 (2)	0.0075 (17)	0.0088 (17)	0.0133 (17)

P1—F6	1.560 (2)	C5—C6	1.394 (4)
P1—F2	1.573 (2)	C5—H5	0.9300
P1—F3	1.579 (2)	C6—C9	1.512 (4)
P1—F4	1.577 (3)	C7—H7A	0.9600
P1—F1	1.584 (2)	C7—H7B	0.9600
P1—F5	1.591 (2)	C7—H7C	0.9600
N1—C11	1.494 (4)	C8—H8A	0.9600
N1—C1	1.494 (3)	C8—H8B	0.9600
N1—C10	1.499 (4)	C8—H8C	0.9600
N1—H1	0.9100	C9—H9A	0.9600
C1—C2	1.388 (4)	C9—H9B	0.9600
C1—C6	1.394 (4)	C9—H9C	0.9600
C2—C3	1.387 (4)	C10—H10A	0.9600
C2—C8	1.512 (4)	C10—H10B	0.9600
C3—C4	1.382 (4)	C10—H10C	0.9600
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.374 (4)	C11—H11B	0.9600
C4—C7	1.515 (4)	C11—H11C	0.9600
F6—P1—F2	91.36 (14)	C6—C5—H5	118.4
F6—P1—F3	91.42 (16)	C1—C6—C5	116.4 (3)
F2—P1—F3	89.77 (14)	C1—C6—C9	126.2 (3)
F6—P1—F4	90.74 (17)	C5—C6—C9	117.4 (3)
F2—P1—F4	89.02 (14)	C4—C7—H7A	109.5
F3—P1—F4	177.55 (15)	C4—C7—H7B	109.5
F6—P1—F1	90.47 (14)	H7A—C7—H7B	109.5
F2—P1—F1	177.89 (15)	C4—C7—H7C	109.5
F3—P1—F1	91.24 (15)	H7A—C7—H7C	109.5
F4—P1—F1	89.91 (15)	H7B—C7—H7C	109.5
F6—P1—F5	178.83 (14)	C2—C8—H8A	109.5
F2—P1—F5	89.71 (14)	C2—C8—H8B	109.5
F3—P1—F5	88.11 (13)	H8A—C8—H8B	109.5
F4—P1—F5	89.76 (15)	C2—C8—H8C	109.5
F1—P1—F5	88.47 (13)	H8A—C8—H8C	109.5
C11—N1—C1	113.6 (2)	H8B—C8—H8C	109.5
C11—N1—C10	113.1 (3)	C6—C9—H9A	109.5
C1—N1—C10	114.6 (2)	C6—C9—H9B	109.5
C11—N1—H1	104.7	H9A—C9—H9B	109.5
C1—N1—H1	104.7	C6—C9—H9C	109.5
C10—N1—H1	104.7	H9A—C9—H9C	109.5
C2—C1—C6	122.7 (2)	H9B—C9—H9C	109.5
C2—C1—N1	116.2 (2)	N1—C10—H10A	109.5
C6—C1—N1	121.1 (2)	N1—C10—H10B	109.5
C1—C2—C3	117.6 (3)	H10A—C10—H10B	109.5
C1—C2—C8	123.0 (3)	N1—C10—H10C	109.5
C3—C2—C8	119.3 (3)	H10A—C10—H10C	109.5
C4—C3—C2	122.3 (3)	H10B—C10—H10C	109.5
C4—C3—H3	118.9	N1—C11—H11A	109.5
C2—C3—H3	118.9	N1—C11—H11B	109.5
C5—C4—C3	117.8 (3)	H11A—C11—H11B	109.5
C5—C4—C7	121.3 (3)	N1—C11—H11C	109.5
C3—C4—C7	120.9 (3)	H11A—C11—H11C	109.5
C4—C5—C6	123.2 (3)	H11B—C11—H11C	109.5
C4—C5—H5	118.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F1	0.91	2.27	2.979 (3)	134
C11—H11A···F4i	0.96	2.47	3.399 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯F1	0.91	2.27	2.979 (3)	134
C11—H11A⋯F4i	0.96	2.47	3.399 (4)	162

Symmetry code: (i) .