Propyl-ammonium 4,4,4-trifluoro-1-(naphthalen-2-yl)butane-1,3-dionate.

The title salt, C(3)H(10)N(+)·C(14)H(8)F(3)O(2) (-), constitutes the first organic crystal containing a residue of 4,4,4-trifluoro-1-(naphthalen-2-yl)butane-1,3-dione. The terminal -CF(3) group is disordered over two locations [occupancy ratio = 0.830 (7):0.170 (7)]. Bond delocalization involving the two carbonyl groups and the α-carbon was observed. The crystal packing is mediated by several supra-molecular inter-actions, namely charged-assisted N-H⋯O hydrogen bonds, C-H⋯F and C-F⋯F short contacts and C-H⋯π inter-actions.

Related literature

For general background to β-diketonates, see: Binnemans (2005 ▶); Bruno, Coelho et al. (2008 ▶); Bruno, Ferreira et al. (2008 ▶); Gago et al. (2005 ▶); Vigato et al. (2009 ▶). For coordination compounds having a naphtho­yltrifluoro­acetonate anion, see: Marandi et al. (2009 ▶); Ishida et al. (2007 ▶); Akhbari & Morsali (2007 ▶); Bruno et al. (2009 ▶); Fernandes et al. (2005 ▶, 2006 ▶); Lunstroot et al. (2009 ▶). For materials containing naphtho­yltrifluoro­acetonate, see: Bruno, Coelho et al. (2008 ▶); Bruno, Ferreira et al. (2008 ▶); Gago et al. (2005 ▶). For standard bond lengths determined by X-ray and neutron diffraction, see: Allen et al. (1987 ▶). For a description of the graph-set notation of hydrogen-bonded aggregates, see: Grell et al. (1999 ▶).

Experimental

Crystal data

C3H10N+·C14H8F3O2 −

M = 325.32

Monoclinic,

a = 16.1038 (11) Å

b = 5.7008 (4) Å

c = 17.2621 (11) Å

β = 91.497 (4)°

V = 1584.20 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 150 K

0.16 × 0.07 × 0.05 mm

Data collection

Bruker X8 KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.982, T max = 0.994

21307 measured reflections

2883 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.117

S = 1.06

2883 reflections

246 parameters

42 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048318/tk5018sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048318/tk5018Isup2.hkl

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

C3H10N+·C14H8F3O2−	F(000) = 680
Mr = 325.32	Dx = 1.364 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4047 reflections
a = 16.1038 (11) Å	θ = 2.4–24.3°
b = 5.7008 (4) Å	µ = 0.11 mm−1
c = 17.2621 (11) Å	T = 150 K
β = 91.497 (4)°	Needle, colourless
V = 1584.20 (19) Å3	0.16 × 0.07 × 0.05 mm
Z = 4

Bruker X8 KappaCCD APEXII diffractometer	2883 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
graphite	Rint = 0.068
ω and φ scans	θmax = 25.4°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −19→19
Tmin = 0.982, Tmax = 0.994	k = −6→6
21307 measured reflections	l = −20→20

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0422P)2 + 1.0164P] where P = (Fo2 + 2Fc2)/3
2883 reflections	(Δ/σ)max = 0.004
246 parameters	Δρmax = 0.20 e Å−3
42 restraints	Δρmin = −0.21 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	Occ. (<1)
O1	−0.17996 (9)	−0.2046 (3)	0.67034 (9)	0.0292 (4)
O2	−0.11872 (9)	0.1894 (3)	0.76308 (9)	0.0290 (4)
C1	−0.08668 (15)	−0.3303 (5)	0.57660 (14)	0.0303 (6)
C2	−0.10632 (14)	−0.1814 (4)	0.64723 (13)	0.0248 (6)
C3	−0.04273 (14)	−0.0443 (5)	0.67711 (14)	0.0281 (6)
H3	0.0101	−0.0584	0.6544	0.034*
C4	−0.05040 (14)	0.1161 (4)	0.73921 (13)	0.0243 (6)
C5	0.02702 (13)	0.2027 (4)	0.77986 (13)	0.0237 (5)
C6	0.02518 (14)	0.4157 (4)	0.82202 (14)	0.0277 (6)
H6	−0.0245	0.5056	0.8219	0.033*
C7	0.09322 (14)	0.4941 (5)	0.86279 (14)	0.0286 (6)
H7	0.0904	0.6381	0.8903	0.034*
C8	0.16822 (14)	0.3635 (4)	0.86470 (13)	0.0233 (6)
C9	0.17081 (13)	0.1478 (4)	0.82323 (13)	0.0209 (5)
C10	0.09915 (13)	0.0741 (4)	0.78071 (13)	0.0231 (5)
H10	0.1010	−0.0679	0.7520	0.028*
C11	0.24530 (14)	0.0163 (4)	0.82469 (14)	0.0266 (6)
H11	0.2476	−0.1278	0.7972	0.032*
C12	0.31392 (15)	0.0937 (5)	0.86504 (14)	0.0305 (6)
H12	0.3636	0.0039	0.8652	0.037*
C13	0.31131 (15)	0.3064 (5)	0.90644 (14)	0.0312 (6)
H13	0.3592	0.3585	0.9347	0.037*
C14	0.24057 (14)	0.4381 (5)	0.90631 (14)	0.0277 (6)
H14	0.2398	0.5813	0.9344	0.033*
F1	−0.1330 (2)	−0.2618 (5)	0.51583 (13)	0.0712 (12)	0.830 (7)
F2	−0.1071 (3)	−0.5535 (4)	0.58622 (18)	0.0660 (12)	0.830 (7)
F3	−0.01008 (15)	−0.3235 (8)	0.5544 (2)	0.0829 (16)	0.830 (7)
F1'	−0.0653 (12)	−0.226 (2)	0.5185 (7)	0.059 (5)	0.170 (7)
F2'	−0.1435 (9)	−0.464 (4)	0.5531 (10)	0.069 (5)	0.170 (7)
F3'	−0.0244 (9)	−0.480 (2)	0.5937 (7)	0.052 (5)	0.170 (7)
N1	0.74144 (12)	0.3443 (4)	0.67812 (11)	0.0252 (5)
H1X	0.7588 (12)	0.495 (2)	0.6613 (12)	0.038*
H1Y	0.7898 (9)	0.262 (3)	0.6976 (12)	0.038*
H1Z	0.7049 (10)	0.363 (4)	0.7203 (10)	0.038*
C15	0.69841 (15)	0.2055 (5)	0.61567 (14)	0.0306 (6)
H15A	0.6813	0.0525	0.6372	0.037*
H15B	0.7380	0.1743	0.5740	0.037*
C16	0.62297 (15)	0.3274 (5)	0.58129 (15)	0.0313 (6)
H16A	0.5845	0.3637	0.6235	0.038*
H16B	0.5940	0.2182	0.5451	0.038*
C17	0.64185 (18)	0.5528 (5)	0.53828 (16)	0.0413 (7)
H17A	0.6681	0.6653	0.5742	0.062*
H17B	0.5901	0.6194	0.5168	0.062*
H17C	0.6796	0.5190	0.4961	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0236 (9)	0.0286 (11)	0.0355 (10)	−0.0029 (8)	0.0063 (7)	−0.0031 (8)
O2	0.0247 (9)	0.0283 (11)	0.0341 (10)	0.0026 (8)	0.0030 (7)	−0.0044 (8)
C1	0.0254 (13)	0.0346 (18)	0.0307 (15)	−0.0062 (13)	0.0011 (11)	−0.0036 (13)
C2	0.0257 (13)	0.0239 (15)	0.0249 (12)	0.0036 (11)	0.0002 (10)	0.0027 (11)
C3	0.0218 (12)	0.0341 (16)	0.0285 (13)	−0.0013 (11)	0.0034 (10)	−0.0056 (12)
C4	0.0237 (12)	0.0230 (14)	0.0265 (13)	−0.0008 (11)	0.0022 (10)	0.0047 (11)
C5	0.0239 (12)	0.0223 (14)	0.0250 (12)	−0.0019 (11)	0.0028 (9)	−0.0010 (11)
C6	0.0252 (13)	0.0220 (15)	0.0359 (14)	0.0042 (11)	0.0024 (10)	−0.0025 (12)
C7	0.0334 (14)	0.0187 (14)	0.0336 (14)	0.0018 (11)	0.0005 (11)	−0.0059 (11)
C8	0.0274 (13)	0.0191 (14)	0.0234 (12)	−0.0018 (10)	0.0025 (10)	0.0001 (11)
C9	0.0246 (12)	0.0162 (14)	0.0222 (12)	−0.0022 (10)	0.0027 (9)	0.0024 (10)
C10	0.0282 (13)	0.0169 (14)	0.0243 (13)	−0.0018 (10)	0.0032 (10)	−0.0015 (11)
C11	0.0288 (13)	0.0216 (15)	0.0295 (13)	0.0030 (11)	0.0035 (10)	0.0004 (11)
C12	0.0243 (13)	0.0336 (17)	0.0337 (14)	0.0021 (11)	0.0013 (11)	0.0048 (13)
C13	0.0275 (13)	0.0354 (17)	0.0305 (14)	−0.0042 (12)	−0.0018 (10)	0.0014 (13)
C14	0.0319 (14)	0.0218 (15)	0.0295 (13)	−0.0039 (11)	0.0013 (10)	−0.0015 (12)
F1	0.105 (3)	0.072 (2)	0.0346 (13)	0.0386 (19)	−0.0269 (14)	−0.0150 (13)
F2	0.120 (3)	0.0212 (15)	0.0590 (18)	0.0016 (15)	0.0397 (18)	−0.0044 (12)
F3	0.0352 (13)	0.128 (4)	0.087 (2)	−0.0328 (17)	0.0303 (14)	−0.079 (3)
F1'	0.090 (10)	0.048 (7)	0.040 (6)	0.008 (7)	0.025 (6)	0.011 (5)
F2'	0.054 (7)	0.082 (10)	0.071 (8)	−0.035 (7)	0.018 (6)	−0.045 (7)
F3'	0.061 (8)	0.047 (7)	0.046 (6)	0.035 (6)	−0.010 (5)	−0.021 (5)
N1	0.0243 (10)	0.0228 (12)	0.0287 (11)	0.0008 (9)	0.0026 (9)	0.0017 (10)
C15	0.0380 (14)	0.0206 (15)	0.0331 (14)	−0.0017 (12)	−0.0006 (11)	−0.0032 (12)
C16	0.0358 (14)	0.0258 (16)	0.0320 (14)	−0.0041 (12)	−0.0034 (11)	−0.0015 (12)
C17	0.0560 (18)	0.0306 (17)	0.0368 (16)	0.0005 (14)	−0.0052 (13)	0.0049 (13)

O1—C2	1.268 (3)	C9—C10	1.415 (3)
O2—C4	1.256 (3)	C10—H10	0.9500
C2—C3	1.377 (3)	C11—C12	1.364 (3)
C3—C4	1.417 (3)	C11—H11	0.9500
C1—F1'	1.223 (11)	C12—C13	1.408 (4)
C1—F2'	1.252 (12)	C12—H12	0.9500
C1—F3	1.302 (3)	C13—C14	1.364 (3)
C1—F2	1.325 (4)	C13—H13	0.9500
C1—F1	1.329 (3)	C14—H14	0.9500
C1—F3'	1.344 (10)	N1—C15	1.493 (3)
C1—C2	1.526 (3)	N1—H1X	0.952 (9)
C3—H3	0.9500	N1—H1Y	0.962 (9)
C4—C5	1.498 (3)	N1—H1Z	0.953 (9)
C5—C10	1.373 (3)	C15—C16	1.508 (3)
C5—C6	1.416 (3)	C15—H15A	0.9900
C6—C7	1.362 (3)	C15—H15B	0.9900
C6—H6	0.9500	C16—C17	1.518 (4)
C7—C8	1.418 (3)	C16—H16A	0.9900
C7—H7	0.9500	C16—H16B	0.9900
C8—C14	1.418 (3)	C17—H17A	0.9800
C8—C9	1.424 (3)	C17—H17B	0.9800
C9—C11	1.414 (3)	C17—H17C	0.9800
F1'—C1—F2'	104.5 (10)	C11—C9—C8	119.0 (2)
F1'—C1—F3	57.0 (8)	C10—C9—C8	118.9 (2)
F2'—C1—F3	127.9 (6)	C5—C10—C9	121.7 (2)
F1'—C1—F2	130.2 (6)	C5—C10—H10	119.2
F3—C1—F2	107.8 (3)	C9—C10—H10	119.2
F1'—C1—F1	51.3 (9)	C12—C11—C9	120.9 (2)
F2'—C1—F1	62.2 (11)	C12—C11—H11	119.6
F3—C1—F1	106.0 (3)	C9—C11—H11	119.6
F2—C1—F1	104.2 (3)	C11—C12—C13	120.2 (2)
F1'—C1—F3'	105.3 (9)	C11—C12—H12	119.9
F2'—C1—F3'	102.5 (11)	C13—C12—H12	119.9
F3—C1—F3'	51.4 (7)	C14—C13—C12	120.6 (2)
F2—C1—F3'	63.1 (7)	C14—C13—H13	119.7
F1—C1—F3'	139.4 (5)	C12—C13—H13	119.7
F1'—C1—C2	117.0 (6)	C13—C14—C8	120.7 (2)
F2'—C1—C2	115.7 (6)	C13—C14—H14	119.6
F3—C1—C2	115.8 (2)	C8—C14—H14	119.6
F2—C1—C2	112.1 (2)	C15—N1—H1X	113.1 (14)
F1—C1—C2	110.1 (2)	C15—N1—H1Y	110.5 (14)
F3'—C1—C2	110.3 (5)	H1X—N1—H1Y	107.8 (12)
O1—C2—C3	129.3 (2)	C15—N1—H1Z	109.1 (14)
O1—C2—C1	114.1 (2)	H1X—N1—H1Z	108.8 (13)
C3—C2—C1	116.6 (2)	H1Y—N1—H1Z	107.3 (12)
C2—C3—C4	124.8 (2)	N1—C15—C16	113.2 (2)
C2—C3—H3	117.6	N1—C15—H15A	108.9
C4—C3—H3	117.6	C16—C15—H15A	108.9
O2—C4—C3	123.9 (2)	N1—C15—H15B	108.9
O2—C4—C5	117.5 (2)	C16—C15—H15B	108.9
C3—C4—C5	118.6 (2)	H15A—C15—H15B	107.7
C10—C5—C6	118.8 (2)	C15—C16—C17	114.4 (2)
C10—C5—C4	121.5 (2)	C15—C16—H16A	108.7
C6—C5—C4	119.6 (2)	C17—C16—H16A	108.7
C7—C6—C5	121.3 (2)	C15—C16—H16B	108.7
C7—C6—H6	119.4	C17—C16—H16B	108.7
C5—C6—H6	119.4	H16A—C16—H16B	107.6
C6—C7—C8	120.8 (2)	C16—C17—H17A	109.5
C6—C7—H7	119.6	C16—C17—H17B	109.5
C8—C7—H7	119.6	H17A—C17—H17B	109.5
C14—C8—C7	122.8 (2)	C16—C17—H17C	109.5
C14—C8—C9	118.6 (2)	H17A—C17—H17C	109.5
C7—C8—C9	118.5 (2)	H17B—C17—H17C	109.5
C11—C9—C10	122.1 (2)
F1'—C1—C2—O1	120.2 (11)	C4—C5—C6—C7	176.8 (2)
F2'—C1—C2—O1	−3.6 (13)	C5—C6—C7—C8	−0.4 (4)
F3—C1—C2—O1	−175.4 (3)	C6—C7—C8—C14	−180.0 (2)
F2—C1—C2—O1	−51.1 (4)	C6—C7—C8—C9	−0.2 (3)
F1—C1—C2—O1	64.4 (3)	C14—C8—C9—C11	−0.3 (3)
F3'—C1—C2—O1	−119.5 (9)	C7—C8—C9—C11	180.0 (2)
F1'—C1—C2—C3	−60.3 (11)	C14—C8—C9—C10	−179.1 (2)
F2'—C1—C2—C3	175.8 (13)	C7—C8—C9—C10	1.1 (3)
F3—C1—C2—C3	4.0 (4)	C6—C5—C10—C9	0.8 (3)
F2—C1—C2—C3	128.3 (3)	C4—C5—C10—C9	−175.8 (2)
F1—C1—C2—C3	−116.2 (3)	C11—C9—C10—C5	179.8 (2)
F3'—C1—C2—C3	60.0 (9)	C8—C9—C10—C5	−1.4 (3)
O1—C2—C3—C4	−4.8 (4)	C10—C9—C11—C12	178.8 (2)
C1—C2—C3—C4	175.9 (2)	C8—C9—C11—C12	0.0 (3)
C2—C3—C4—O2	−16.0 (4)	C9—C11—C12—C13	0.4 (4)
C2—C3—C4—C5	163.2 (2)	C11—C12—C13—C14	−0.4 (4)
O2—C4—C5—C10	154.1 (2)	C12—C13—C14—C8	0.1 (4)
C3—C4—C5—C10	−25.2 (3)	C7—C8—C14—C13	180.0 (2)
O2—C4—C5—C6	−22.4 (3)	C9—C8—C14—C13	0.2 (3)
C3—C4—C5—C6	158.2 (2)	N1—C15—C16—C17	65.1 (3)
C10—C5—C6—C7	0.1 (4)

Cg is the centroid of the C8–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
Strong hydrogen bonds—···..	.	.	.	.
N1—H1X···O1i	0.95 (1)	1.98 (1)	2.871 (3)	155 (2)
N1—H1Y···O2ii	0.96 (1)	1.88 (1)	2.798 (3)	159 (2)
N1—H1Z···O1iii	0.95 (1)	1.98 (1)	2.835 (2)	148.(2)
N1—H1Z···O2iii	0.95 (1)	2.34 (2)	2.985 (3)	124.(1)
C—H···F contacts—···..	.	.	.	.
C14—H14···F1iv	0.95	2.66	3.305 (4)	126
C13—H13···F1iv	0.95	2.69	3.320 (4)	124
C13—H13···F3iii	0.95	2.64	3.337 (4)	130
C—H···π contacts—···..	.	.	.	.
C11—H11···Cgv	0.95	2.93	3.677 (3)	136
C17—H17C···Cgvi	0.98	2.87	3.786 (3)	157
F···F contact—···..	.	.	.	.
C1—F3···F3vii	1.302 (3)	2.778 (6)	3.409 (4)	107.8 (2)

Table 1

Selected bond lengths (Å)

O1—C2	1.268 (3)
O2—C4	1.256 (3)
C2—C3	1.377 (3)
C3—C4	1.417 (3)

Table 2

Selected short distance supra­molecular inter­actions (Å, °)

Cg is the centroid of the C8–C14 ring.

A—B⋯C	A—B	B⋯C	A⋯C	A—B⋯C
Strong hydrogen bonds
N1—H1X⋯O1i	0.95 (1)	1.98 (1)	2.871 (3)	155 (2)
N1—H1Y⋯O2ii	0.96 (1)	1.88 (1)	2.798 (3)	159 (2)
N1—H1Z⋯O1iii	0.95 (1)	1.98 (1)	2.835 (2)	148 (2)
N1—H1Z⋯O2iii	0.95 (1)	2.34 (2)	2.985 (3)	124 (1)
C—H⋯F contacts
C14—H14⋯F1iv	0.95	2.66	3.305 (4)	126
C13—H13⋯F1iv	0.95	2.69	3.320 (4)	124
C13—H13⋯F3iii	0.95	2.64	3.337 (4)	130
C—H⋯π contacts
C11—H11⋯Cgv	0.95	2.93	3.677 (3)	136
C17—H17C⋯Cgvi	0.98	2.87	3.786 (3)	157
F⋯F contact
C1—F3⋯F3vii	1.30 (1)	2.78 (1)	3.409 (4)	108 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .