(±)-Bis(1-carb-oxy-2-phenyl-ethanaminium) hexa-fluoro-silicate(VI).

The asymmetric unit of the title fluoro-silicate salt, 2C(9)H(12)NO(2) (+)·SiF(6) (2-), consists of a phenylalaninium cation and half of a fluorosilicate anion, the Si atom being located on an inversion center. In the crystal, all of the F atoms act as hydrogen-bond acceptors and link the cations through different graph-set motifs, forming layers developing parallel to (100).

Related literature

For applications of fluoro­silicate salts, see: Katayama et al. (2001 ▶); Kalem (2004 ▶); Airoldi & De Farias (2000 ▶); Han et al. (2000 ▶); Gelmboldt (1989 ▶); Gelmboldt et al. (2007 ▶). For our previous work on hydrogen-bonding inter­actions in the crystal structures of protonated amines, see: Bouacida et al. (2005 ▶, 2007 ▶, 2009 ▶); Benslimane et al. (2007 ▶); Bouacida (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶); Janiak (2000 ▶).

Experimental

Crystal data

2C9H12NO2 +·SiF6 2−

M = 474.48

Monoclinic,

a = 11.183 (2) Å

b = 5.7531 (10) Å

c = 17.000 (4) Å

β = 105.59 (2)°

V = 1053.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.59 × 0.50 × 0.37 mm

Data collection

Nonius KappaCCD diffractometer

2412 measured reflections

2412 independent reflections

1917 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.03

2412 reflections

144 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Otwinowski & Minor, 1997 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2003 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021587/ez2295sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021587/ez2295Isup2.hkl

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

2C9H12NO2+·SiF62−	F(000) = 492
Mr = 474.48	Dx = 1.496 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4769 reflections
a = 11.183 (2) Å	θ = 5.0–27.5°
b = 5.7531 (10) Å	µ = 0.19 mm−1
c = 17.000 (4) Å	T = 295 K
β = 105.59 (2)°	Block, white
V = 1053.5 (4) Å3	0.59 × 0.50 × 0.37 mm
Z = 2

Nonius KappaCCD diffractometer	1917 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 5.0°
Detector resolution: 9 pixels mm-1	h = −14→13
CCD rotation images, thick slices scans	k = 0→7
2412 measured reflections	l = 0→22
2412 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0329P)2 + 0.2833P] where P = (Fo2 + 2Fc2)/3
2412 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
Si1	0.0000	0.5000	0.5000	0.02345 (13)
F1	0.07812 (8)	0.54094 (14)	0.43002 (5)	0.0345 (2)
F2	−0.11419 (8)	0.36774 (15)	0.42781 (5)	0.0371 (2)
F3	0.07100 (8)	0.24091 (13)	0.52540 (5)	0.0346 (2)
O1	0.17794 (11)	0.0905 (2)	0.21347 (6)	0.0403 (3)
H1	0.1700	0.0176	0.1709	0.060*
O2	0.10064 (12)	−0.23340 (19)	0.25348 (6)	0.0431 (3)
N2	0.05617 (12)	0.0158 (2)	0.37935 (7)	0.0307 (3)
H2A	−0.0126	0.0728	0.3455	0.046*
H2B	0.0661	0.0763	0.4289	0.046*
H2C	0.0499	−0.1381	0.3820	0.046*
C2	0.16410 (14)	0.0759 (2)	0.34897 (8)	0.0293 (3)
H2	0.1696	0.2449	0.3435	0.035*
C1	0.14352 (13)	−0.0392 (2)	0.26636 (8)	0.0289 (3)
C3	0.28085 (15)	−0.0161 (3)	0.41120 (9)	0.0410 (4)
H3A	0.2872	0.0580	0.4634	0.049*
H3B	0.2708	−0.1816	0.4182	0.049*
C4	0.40009 (15)	0.0225 (3)	0.38861 (9)	0.0374 (4)
C6	0.55760 (19)	−0.1169 (4)	0.32857 (12)	0.0563 (5)
H6	0.5865	−0.2308	0.2994	0.068*
C9	0.47022 (18)	0.2226 (3)	0.41237 (11)	0.0493 (4)
H9	0.4405	0.3395	0.4399	0.059*
C8	0.58322 (19)	0.2497 (4)	0.39562 (12)	0.0585 (5)
H8	0.6297	0.3835	0.4124	0.070*
C5	0.44501 (17)	−0.1453 (3)	0.34602 (11)	0.0469 (4)
H5	0.3988	−0.2791	0.3289	0.056*
C7	0.62729 (18)	0.0799 (4)	0.35423 (12)	0.0580 (5)
H7	0.7041	0.0975	0.3435	0.070*

	U11	U22	U33	U12	U13	U23
Si1	0.0314 (3)	0.0221 (2)	0.0178 (2)	−0.0039 (2)	0.00823 (19)	−0.00049 (18)
F1	0.0451 (5)	0.0334 (4)	0.0310 (4)	−0.0022 (4)	0.0206 (4)	0.0025 (3)
F2	0.0414 (5)	0.0393 (5)	0.0281 (4)	−0.0112 (4)	0.0049 (4)	−0.0044 (3)
F3	0.0472 (5)	0.0277 (4)	0.0311 (4)	0.0050 (4)	0.0141 (4)	0.0041 (3)
O1	0.0516 (7)	0.0483 (6)	0.0232 (5)	−0.0117 (5)	0.0137 (5)	−0.0002 (4)
O2	0.0606 (8)	0.0396 (6)	0.0310 (5)	−0.0123 (5)	0.0156 (5)	−0.0066 (5)
N2	0.0388 (7)	0.0284 (6)	0.0283 (6)	0.0025 (5)	0.0147 (5)	0.0024 (5)
C2	0.0359 (8)	0.0285 (7)	0.0252 (6)	−0.0043 (6)	0.0110 (6)	−0.0002 (5)
C1	0.0274 (7)	0.0352 (8)	0.0238 (6)	0.0002 (6)	0.0065 (5)	0.0010 (5)
C3	0.0388 (9)	0.0543 (10)	0.0265 (7)	−0.0026 (7)	0.0031 (6)	0.0038 (7)
C4	0.0324 (8)	0.0468 (9)	0.0280 (7)	−0.0026 (7)	−0.0003 (6)	0.0029 (6)
C6	0.0453 (11)	0.0653 (12)	0.0589 (11)	0.0071 (9)	0.0150 (9)	−0.0007 (9)
C9	0.0484 (11)	0.0497 (10)	0.0441 (9)	−0.0052 (8)	0.0027 (8)	−0.0041 (8)
C8	0.0491 (12)	0.0588 (12)	0.0586 (11)	−0.0176 (10)	−0.0009 (9)	0.0077 (10)
C5	0.0412 (10)	0.0472 (10)	0.0502 (10)	−0.0055 (8)	0.0088 (8)	−0.0044 (7)
C7	0.0349 (10)	0.0765 (14)	0.0596 (11)	−0.0056 (10)	0.0071 (9)	0.0138 (10)

Si1—F1i	1.6711 (9)	C2—H2	0.9800
Si1—F1	1.6711 (9)	C3—C4	1.500 (2)
Si1—F3i	1.6895 (8)	C3—H3A	0.9700
Si1—F3	1.6895 (8)	C3—H3B	0.9700
Si1—F2	1.6952 (8)	C4—C5	1.380 (3)
Si1—F2i	1.6952 (9)	C4—C9	1.391 (2)
O1—C1	1.3036 (17)	C6—C7	1.377 (3)
O1—H1	0.8200	C6—C5	1.379 (3)
O2—C1	1.2121 (17)	C6—H6	0.9300
N2—C2	1.4760 (18)	C9—C8	1.377 (3)
N2—H2A	0.8900	C9—H9	0.9300
N2—H2B	0.8900	C8—C7	1.371 (3)
N2—H2C	0.8900	C8—H8	0.9300
C2—C1	1.5135 (19)	C5—H5	0.9300
C2—C3	1.537 (2)	C7—H7	0.9300
F1i—Si1—F1	180.0	O2—C1—O1	125.37 (13)
F1i—Si1—F3i	90.38 (4)	O2—C1—C2	121.67 (13)
F1—Si1—F3i	89.62 (4)	O1—C1—C2	112.95 (12)
F1i—Si1—F3	89.62 (4)	C4—C3—C2	114.97 (12)
F1—Si1—F3	90.38 (4)	C4—C3—H3A	108.5
F3i—Si1—F3	180.0	C2—C3—H3A	108.5
F1i—Si1—F2	90.90 (5)	C4—C3—H3B	108.5
F1—Si1—F2	89.10 (4)	C2—C3—H3B	108.5
F3i—Si1—F2	90.00 (4)	H3A—C3—H3B	107.5
F3—Si1—F2	90.00 (4)	C5—C4—C9	118.37 (17)
F1i—Si1—F2i	89.10 (4)	C5—C4—C3	120.33 (15)
F1—Si1—F2i	90.90 (5)	C9—C4—C3	121.26 (16)
F3i—Si1—F2i	90.00 (4)	C7—C6—C5	120.05 (19)
F3—Si1—F2i	90.00 (4)	C7—C6—H6	120.0
F2—Si1—F2i	180.0	C5—C6—H6	120.0
C1—O1—H1	109.5	C8—C9—C4	120.73 (18)
C2—N2—H2A	109.5	C8—C9—H9	119.6
C2—N2—H2B	109.5	C4—C9—H9	119.6
H2A—N2—H2B	109.5	C7—C8—C9	120.13 (18)
C2—N2—H2C	109.5	C7—C8—H8	119.9
H2A—N2—H2C	109.5	C9—C8—H8	119.9
H2B—N2—H2C	109.5	C6—C5—C4	120.84 (17)
N2—C2—C1	106.69 (11)	C6—C5—H5	119.6
N2—C2—C3	107.57 (11)	C4—C5—H5	119.6
C1—C2—C3	112.16 (13)	C8—C7—C6	119.84 (19)
N2—C2—H2	110.1	C8—C7—H7	120.1
C1—C2—H2	110.1	C6—C7—H7	120.1
C3—C2—H2	110.1
N2—C2—C1—O2	−39.96 (18)	C4—C9—C8—C7	0.8 (3)
C3—C2—C1—O2	77.58 (18)	C7—C6—C5—C4	0.5 (3)
N2—C2—C1—O1	140.88 (13)	C9—C4—C5—C6	1.0 (2)
C3—C2—C1—O1	−101.58 (15)	C3—C4—C5—C6	−176.65 (15)
N2—C2—C3—C4	177.95 (13)	C9—C8—C7—C6	0.8 (3)
C1—C2—C3—C4	60.93 (18)	C5—C6—C7—C8	−1.4 (3)
C2—C3—C4—C5	−92.09 (19)	C4—C3—C2—C1	60.93 (18)
C2—C3—C4—C9	90.30 (18)	C4—C3—C2—N2	177.95 (13)
C5—C4—C9—C8	−1.7 (2)	C3—C2—C1—O1	−101.58 (15)
C3—C4—C9—C8	175.98 (15)	C3—C2—C1—O2	77.58 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···F2ii	0.82	1.84	2.6456 (14)	167
N2—H2A···O2iii	0.89	2.04	2.8511 (17)	151
N2—H2B···F3	0.89	1.88	2.7656 (15)	171
N2—H2C···F1iv	0.89	2.01	2.8549 (15)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯F2i	0.82	1.84	2.6456 (14)	167
N2—H2A⋯O2ii	0.89	2.04	2.8511 (17)	151
N2—H2B⋯F3	0.89	1.88	2.7656 (15)	171
N2—H2C⋯F1iii	0.89	2.01	2.8549 (15)	158

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