4-Ethoxy-anilinium hexa-fluoro-phosphate monohydrate.

In the crystal of the title compound, C(8)H(12)NO(+)·PF(6) (-)·H(2)O, inter-molecular N-H⋯F, N-H⋯O and O-H⋯F hydrogen bonds link the mol-ecules into chains along the c axis and C-H⋯π contacts further stabilize the structure. The F atoms of one of the hexa-fluoro-phosphate anions are disordered over two sets of sites with site-occupancy factors of 0.27 (3) and 0.73 (3).

Related literature

For related structures, see: Fu (2009a ▶,b ▶). The title compound was studied as part of our search for ferroelectric compounds, which usually have a phase transition.For background to phase transition materials, see: Li et al. (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C8H12NO+·PF6 −·H2O

M = 301.17

Monoclinic,

a = 17.498 (4) Å

b = 5.1236 (10) Å

c = 14.793 (3) Å

β = 111.68 (3)°

V = 1232.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.4 × 0.3 × 0.2 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.900, T max = 0.943

12124 measured reflections

2820 independent reflections

1890 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.164

S = 1.05

2820 reflections

226 parameters

235 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810018404/zq2040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018404/zq2040Isup2.hkl

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

C8H12NO+·PF6−·H2O	F(000) = 616
Mr = 301.17	Dx = 1.623 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4774 reflections
a = 17.498 (4) Å	θ = 3.1–27.7°
b = 5.1236 (10) Å	µ = 0.29 mm−1
c = 14.793 (3) Å	T = 298 K
β = 111.68 (3)°	Prism, colourless
V = 1232.4 (4) Å3	0.4 × 0.3 × 0.2 mm
Z = 4

Rigaku SCXmini diffractometer	2820 independent reflections
Radiation source: fine-focus sealed tube	1890 reflections with I > 2σ(I)
graphite	Rint = 0.054
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −22→22
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −6→6
Tmin = 0.900, Tmax = 0.943	l = −19→19
12124 measured 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0764P)2 + 0.6523P] where P = (Fo2 + 2Fc2)/3
2820 reflections	(Δ/σ)max = 0.003
226 parameters	Δρmax = 0.45 e Å−3
235 restraints	Δρmin = −0.48 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 > 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.15275 (14)	0.3564 (5)	0.42609 (17)	0.0414 (6)
H1A	0.1427	0.4860	0.3832	0.050*
H1B	0.1304	0.3936	0.4697	0.050*
H1C	0.1311	0.2092	0.3953	0.050*
O1	0.49349 (12)	0.2376 (5)	0.60339 (18)	0.0624 (7)
C1	0.40946 (18)	0.2556 (6)	0.5644 (2)	0.0458 (7)
C4	0.24232 (16)	0.3242 (5)	0.47587 (19)	0.0366 (6)
C3	0.29478 (19)	0.4801 (6)	0.4497 (2)	0.0515 (8)
H3A	0.2739	0.6074	0.4021	0.062*
C5	0.27196 (18)	0.1368 (7)	0.5450 (2)	0.0497 (8)
H5A	0.2360	0.0333	0.5625	0.060*
C6	0.35635 (19)	0.1007 (7)	0.5895 (2)	0.0558 (9)
H6A	0.3769	−0.0286	0.6364	0.067*
C2	0.37808 (19)	0.4465 (7)	0.4943 (3)	0.0561 (9)
H2A	0.4137	0.5527	0.4773	0.067*
C8	0.6217 (2)	0.0478 (10)	0.6954 (3)	0.0783 (12)
H8A	0.6483	−0.0935	0.7380	0.117*
H8B	0.6405	0.2108	0.7279	0.117*
H8C	0.6347	0.0396	0.6378	0.117*
C7	0.5304 (2)	0.0266 (8)	0.6678 (3)	0.0632 (10)
H7A	0.5107	−0.1390	0.6359	0.076*
H7B	0.5164	0.0372	0.7254	0.076*
O1W	0.08195 (12)	0.8613 (5)	0.44539 (16)	0.0473 (5)
H1WB	0.0467 (16)	0.843 (9)	0.3908 (11)	0.086 (15)*
H1WA	0.071 (2)	0.856 (9)	0.4948 (14)	0.086 (15)*
P1	0.11668 (4)	0.96937 (15)	0.18642 (5)	0.0396 (3)
F3	0.0519 (7)	1.103 (3)	0.2240 (8)	0.064 (2)	0.73 (3)
F5	0.1765 (9)	0.833 (3)	0.1430 (10)	0.065 (2)	0.73 (3)
F4	0.0451 (7)	0.782 (2)	0.1246 (9)	0.072 (2)	0.73 (3)
F1	0.0911 (6)	1.1714 (17)	0.0948 (6)	0.0618 (15)	0.73 (3)
F2	0.1410 (8)	0.783 (2)	0.2777 (7)	0.086 (2)	0.73 (3)
F6	0.1869 (6)	1.169 (2)	0.2477 (7)	0.0704 (18)	0.73 (3)
F6'	0.1908 (13)	1.081 (6)	0.2715 (16)	0.066 (4)	0.27 (3)
F4'	0.0396 (15)	0.830 (6)	0.1040 (17)	0.053 (4)	0.27 (3)
F2'	0.1153 (17)	0.730 (5)	0.256 (2)	0.070 (4)	0.27 (3)
F3'	0.0594 (18)	1.160 (7)	0.2229 (19)	0.056 (4)	0.27 (3)
F5'	0.184 (3)	0.796 (8)	0.164 (3)	0.062 (4)	0.27 (3)
F1'	0.1166 (18)	1.168 (5)	0.1154 (19)	0.075 (4)	0.27 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0383 (13)	0.0429 (13)	0.0428 (13)	−0.0011 (11)	0.0147 (11)	−0.0042 (11)
O1	0.0333 (11)	0.0710 (15)	0.0758 (16)	0.0024 (11)	0.0119 (11)	0.0209 (13)
C1	0.0335 (14)	0.0500 (17)	0.0516 (17)	0.0022 (13)	0.0128 (13)	0.0029 (14)
C4	0.0337 (14)	0.0378 (15)	0.0383 (14)	−0.0002 (12)	0.0132 (12)	−0.0041 (12)
C3	0.0425 (16)	0.0509 (18)	0.0603 (19)	0.0031 (14)	0.0181 (15)	0.0191 (16)
C5	0.0406 (17)	0.0564 (19)	0.0508 (17)	−0.0050 (15)	0.0153 (14)	0.0124 (15)
C6	0.0443 (18)	0.060 (2)	0.0577 (19)	0.0035 (16)	0.0128 (15)	0.0216 (17)
C2	0.0425 (17)	0.0553 (19)	0.073 (2)	−0.0024 (15)	0.0237 (16)	0.0172 (17)
C8	0.045 (2)	0.108 (3)	0.071 (3)	0.018 (2)	0.0099 (19)	0.020 (2)
C7	0.0450 (18)	0.073 (2)	0.064 (2)	0.0094 (18)	0.0113 (16)	0.0147 (19)
O1W	0.0395 (12)	0.0532 (13)	0.0448 (13)	−0.0011 (10)	0.0105 (11)	0.0014 (11)
P1	0.0366 (4)	0.0479 (5)	0.0323 (4)	0.0065 (3)	0.0103 (3)	−0.0011 (3)
F3	0.055 (3)	0.082 (6)	0.065 (3)	0.018 (3)	0.034 (2)	−0.005 (3)
F5	0.055 (3)	0.086 (4)	0.054 (5)	0.022 (2)	0.019 (4)	−0.012 (3)
F4	0.068 (3)	0.074 (4)	0.071 (5)	−0.032 (3)	0.022 (3)	−0.011 (3)
F1	0.054 (4)	0.073 (2)	0.054 (3)	0.014 (3)	0.014 (2)	0.026 (2)
F2	0.092 (6)	0.101 (5)	0.054 (3)	0.027 (4)	0.015 (3)	0.036 (3)
F6	0.057 (2)	0.078 (4)	0.066 (4)	−0.013 (3)	0.011 (2)	−0.025 (3)
F6'	0.042 (4)	0.089 (9)	0.054 (7)	0.011 (6)	0.004 (5)	−0.032 (6)
F4'	0.044 (5)	0.075 (8)	0.040 (6)	−0.004 (5)	0.015 (4)	−0.013 (6)
F2'	0.074 (10)	0.075 (7)	0.060 (8)	0.017 (6)	0.025 (6)	0.029 (6)
F3'	0.048 (6)	0.066 (9)	0.042 (6)	0.022 (6)	0.003 (5)	−0.007 (5)
F5'	0.050 (6)	0.087 (10)	0.049 (10)	0.018 (6)	0.018 (7)	−0.017 (7)
F1'	0.065 (10)	0.081 (6)	0.066 (7)	−0.007 (7)	0.010 (6)	0.035 (6)

N1—C4	1.474 (4)	C8—H8B	0.9600
N1—H1A	0.8900	C8—H8C	0.9600
N1—H1B	0.8900	C7—H7A	0.9700
N1—H1C	0.8900	C7—H7B	0.9700
O1—C1	1.370 (4)	O1W—H1WB	0.821 (10)
O1—C7	1.428 (4)	O1W—H1WA	0.82 (3)
C1—C6	1.373 (4)	P1—F1'	1.46 (2)
C1—C2	1.384 (4)	P1—F6'	1.546 (18)
C4—C5	1.358 (4)	P1—F4	1.575 (10)
C4—C3	1.376 (4)	P1—F5	1.578 (13)
C3—C2	1.371 (4)	P1—F2	1.580 (8)
C3—H3A	0.9300	P1—F3	1.590 (11)
C5—C6	1.389 (4)	P1—F6	1.598 (7)
C5—H5A	0.9300	P1—F5'	1.60 (4)
C6—H6A	0.9300	P1—F2'	1.61 (2)
C2—H2A	0.9300	P1—F4'	1.61 (3)
C8—C7	1.500 (5)	P1—F3'	1.63 (3)
C8—H8A	0.9600	P1—F1	1.632 (7)
C4—N1—H1A	109.5	F6'—P1—F3	92.8 (9)
C4—N1—H1B	109.4	F4—P1—F3	87.1 (6)
H1A—N1—H1B	109.5	F5—P1—F3	176.5 (7)
C4—N1—H1C	109.5	F2—P1—F3	87.9 (6)
H1A—N1—H1C	109.5	F1'—P1—F6	76.1 (9)
H1B—N1—H1C	109.5	F4—P1—F6	177.8 (5)
C1—O1—C7	118.8 (3)	F5—P1—F6	91.6 (8)
O1—C1—C6	125.2 (3)	F2—P1—F6	89.7 (3)
O1—C1—C2	115.5 (3)	F3—P1—F6	91.4 (6)
C6—C1—C2	119.4 (3)	F1'—P1—F5'	92.5 (15)
C5—C4—C3	120.9 (3)	F6'—P1—F5'	85.2 (18)
C5—C4—N1	119.7 (3)	F4—P1—F5'	91.5 (18)
C3—C4—N1	119.4 (3)	F2—P1—F5'	81.6 (13)
C2—C3—C4	119.5 (3)	F3—P1—F5'	169.4 (13)
C2—C3—H3A	120.2	F6—P1—F5'	90.3 (18)
C4—C3—H3A	120.2	F1'—P1—F2'	174.5 (15)
C4—C5—C6	119.6 (3)	F6'—P1—F2'	88.1 (9)
C4—C5—H5A	120.2	F4—P1—F2'	73.3 (9)
C6—C5—H5A	120.2	F5—P1—F2'	95.5 (12)
C1—C6—C5	120.1 (3)	F3—P1—F2'	85.4 (12)
C1—C6—H6A	119.9	F6—P1—F2'	108.2 (8)
C5—C6—H6A	119.9	F5'—P1—F2'	84.1 (17)
C3—C2—C1	120.4 (3)	F1'—P1—F4'	89.3 (11)
C3—C2—H2A	119.8	F6'—P1—F4'	174.7 (12)
C1—C2—H2A	119.8	F5—P1—F4'	89.5 (10)
C7—C8—H8A	109.5	F2—P1—F4'	105.3 (9)
C7—C8—H8B	109.5	F3—P1—F4'	87.1 (10)
H8A—C8—H8B	109.5	F6—P1—F4'	164.9 (9)
C7—C8—H8C	109.5	F5'—P1—F4'	94.0 (19)
H8A—C8—H8C	109.5	F2'—P1—F4'	86.7 (10)
H8B—C8—H8C	109.5	F1'—P1—F3'	89.0 (15)
O1—C7—C8	107.4 (3)	F6'—P1—F3'	86.7 (13)
O1—C7—H7A	110.2	F4—P1—F3'	96.0 (12)
C8—C7—H7A	110.2	F5—P1—F3'	169.1 (14)
O1—C7—H7B	110.2	F2—P1—F3'	94.9 (12)
C8—C7—H7B	110.2	F6—P1—F3'	82.3 (12)
H7A—C7—H7B	108.5	F5'—P1—F3'	171.8 (19)
H1WB—O1W—H1WA	122 (2)	F2'—P1—F3'	94.9 (17)
F1'—P1—F6'	96.0 (11)	F4'—P1—F3'	94.1 (14)
F1'—P1—F4	102.6 (9)	F6'—P1—F1	109.3 (11)
F6'—P1—F4	161.3 (10)	F4—P1—F1	89.4 (4)
F1'—P1—F5	80.8 (12)	F5—P1—F1	87.8 (5)
F6'—P1—F5	90.7 (10)	F2—P1—F1	177.8 (5)
F4—P1—F5	89.9 (8)	F3—P1—F1	90.3 (5)
F1'—P1—F2	164.6 (8)	F6—P1—F1	89.0 (3)
F6'—P1—F2	69.4 (10)	F5'—P1—F1	100.2 (13)
F4—P1—F2	91.9 (4)	F2'—P1—F1	162.3 (8)
F5—P1—F2	94.0 (6)	F4'—P1—F1	75.9 (10)
F1'—P1—F3	98.1 (12)	F3'—P1—F1	83.1 (11)
C7—O1—C1—C6	6.9 (5)	C2—C1—C6—C5	−0.3 (5)
C7—O1—C1—C2	−172.9 (3)	C4—C5—C6—C1	0.7 (5)
C5—C4—C3—C2	−0.2 (5)	C4—C3—C2—C1	0.7 (5)
N1—C4—C3—C2	−178.5 (3)	O1—C1—C2—C3	179.3 (3)
C3—C4—C5—C6	−0.5 (5)	C6—C1—C2—C3	−0.4 (5)
N1—C4—C5—C6	177.8 (3)	C1—O1—C7—C8	177.4 (3)
O1—C1—C6—C5	180.0 (3)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F2'	0.89	2.16	3.03 (2)	167
N1—H1A···F2	0.89	2.17	3.049 (10)	169
N1—H1B···F1i	0.89	2.22	3.066 (8)	158
N1—H1B···F1'i	0.89	2.28	3.09 (3)	152
N1—H1C···O1Wii	0.89	2.22	2.883 (3)	131
N1—H1C···F3ii	0.89	2.46	3.137 (12)	133
N1—H1C···F3'ii	0.89	2.40	3.01 (3)	126
N1—H1C···F6'ii	0.89	2.51	2.96 (2)	112
O1W—H1WB···F3'iii	0.82 (1)	2.20 (3)	2.97 (3)	156 (4)
O1W—H1WB···F3iii	0.82 (1)	2.28 (3)	3.030 (12)	152 (4)
O1W—H1WA···F4i	0.82 (3)	2.24 (2)	3.040 (12)	164 (4)
O1W—H1WA···F4'i	0.82 (3)	2.11 (3)	2.88 (2)	155 (4)
O1W—H1WA···F5i	0.82 (3)	2.48 (4)	2.951 (16)	117 (3)
C8—H8C···Cg1iv	0.96	3.16	4.023 (5)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯F2′	0.89	2.16	3.03 (2)	167
N1—H1A⋯F2	0.89	2.17	3.049 (10)	169
N1—H1B⋯F1i	0.89	2.22	3.066 (8)	158
N1—H1B⋯F1′i	0.89	2.28	3.09 (3)	152
N1—H1C⋯O1Wii	0.89	2.22	2.883 (3)	131
N1—H1C⋯F3ii	0.89	2.46	3.137 (12)	133
N1—H1C⋯F3′ii	0.89	2.40	3.01 (3)	126
N1—H1C⋯F6′ii	0.89	2.51	2.96 (2)	112
O1W—H1WB⋯F3′iii	0.82 (1)	2.20 (3)	2.97 (3)	156 (4)
O1W—H1WB⋯F3iii	0.82 (1)	2.28 (3)	3.030 (12)	152 (4)
O1W—H1WA⋯F4i	0.82 (3)	2.24 (2)	3.040 (12)	164 (4)
O1W—H1WA⋯F4′i	0.82 (3)	2.11 (3)	2.88 (2)	155 (4)
O1W—H1WA⋯F5i	0.82 (3)	2.48 (4)	2.951 (16)	117 (3)
C8—H8C⋯Cg1iv	0.96	3.16	4.023 (5)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .