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In the title compound, C5H12NO2+·C2F3O2, the valine mol­ecule is in a cationic state, with a protonated amino group and an uncharged carboxylic acid group. The trifluoro­acetic acid mol­ecule is deprotonated and it displays rotational disorder. Inversion-related valinium residues are linked by N—H...O hydrogen bonds into a dimer. The dimers and the trifluoro­acetate anions are alternately connected by O—H...O and N—H...O hydrogen bonds to form a layer parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026638/ci2098sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026638/ci2098Isup2.hkl
Contains datablock I

CCDC reference: 618164

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in main residue
  • R factor = 0.073
  • wR factor = 0.255
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C2
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.255 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.26 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 17.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

DL-valinium trifluoroacetate top
Crystal data top
C5H12NO2+·C2F3O2Z = 2
Mr = 231.18F(000) = 240
Triclinic, P1Dx = 1.407 Mg m3
Dm = 1.40 Mg m3
Dm measured by flotation
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7282 (6) ÅCell parameters from 1908 reflections
b = 9.0830 (4) Åθ = 2.2–25°
c = 9.2148 (7) ŵ = 0.14 mm1
α = 98.460 (1)°T = 293 K
β = 91.990 (1)°Prism, colourless
γ = 101.050 (2)°0.3 × 0.3 × 0.3 mm
V = 545.53 (7) Å3
Data collection top
Nonius MACH3 four-circle
diffractometer
887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω scansh = 17
Absorption correction: ψ scan
(North et al., 1968)
k = 1010
Tmin = 0.958, Tmax = 0.958l = 1010
2438 measured reflections3 standard reflections every 60 min
1908 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.255H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1435P)2 + 0.0816P]
where P = (Fo2 + 2Fc2)/3
1908 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.31 e Å3
42 restraintsΔρmin = 0.35 e Å3
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3319 (5)0.2778 (3)0.6599 (4)0.0673 (11)
O20.1914 (7)0.0382 (4)0.6399 (5)0.1009 (16)
C10.3335 (8)0.1457 (5)0.6754 (5)0.0545 (13)
C20.5244 (10)0.1149 (7)0.7448 (7)0.0836 (18)
F10.525 (2)0.0335 (11)0.702 (2)0.142 (6)0.438 (14)
F20.530 (2)0.131 (3)0.8882 (10)0.139 (6)0.438 (14)
F30.6968 (15)0.1856 (19)0.7066 (19)0.118 (5)0.438 (14)
F1A0.4986 (17)0.0158 (16)0.8315 (17)0.142 (5)0.562 (14)
F2A0.6218 (18)0.2393 (12)0.8371 (15)0.146 (5)0.562 (14)
F3A0.6589 (17)0.0905 (19)0.6503 (13)0.147 (5)0.562 (14)
N10.0139 (6)0.2559 (4)0.4442 (4)0.0532 (11)
H1A0.09340.26780.52610.080*
H1B0.05980.16190.42740.080*
H1C0.06820.32230.45460.080*
O30.4202 (5)0.4606 (4)0.2703 (4)0.0702 (12)
H30.49270.54440.29740.105*
O40.2392 (5)0.5328 (3)0.4553 (4)0.0620 (11)
C30.2727 (7)0.4396 (5)0.3572 (5)0.0494 (12)
C40.1414 (7)0.2821 (5)0.3184 (5)0.0514 (13)
H40.22950.20740.30700.062*
C50.0059 (8)0.2620 (6)0.1752 (6)0.0631 (14)
H50.09690.16950.17440.076*
C60.1077 (10)0.3891 (8)0.1706 (7)0.091 (2)
H6A0.18920.37110.07970.136*
H6B0.01270.48370.17750.136*
H6C0.19370.39340.25150.136*
C70.1243 (11)0.2342 (8)0.0408 (7)0.095 (2)
H7A0.03620.22210.04620.143*
H7B0.17770.14370.04240.143*
H7C0.23400.31910.04080.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.066 (2)0.0309 (18)0.097 (3)0.0113 (15)0.0108 (19)0.0159 (16)
O20.111 (4)0.040 (2)0.129 (4)0.034 (2)0.027 (3)0.010 (2)
C10.068 (3)0.035 (3)0.055 (3)0.001 (2)0.001 (2)0.008 (2)
C20.101 (5)0.069 (4)0.090 (5)0.030 (4)0.011 (4)0.024 (4)
F10.152 (9)0.102 (7)0.186 (11)0.072 (6)0.007 (7)0.014 (6)
F20.139 (9)0.180 (11)0.106 (8)0.042 (8)0.008 (6)0.042 (7)
F30.092 (7)0.127 (8)0.141 (9)0.013 (6)0.015 (6)0.055 (7)
F1A0.161 (7)0.137 (8)0.148 (9)0.021 (6)0.015 (6)0.098 (7)
F2A0.134 (7)0.134 (7)0.151 (8)0.020 (6)0.081 (6)0.004 (6)
F3A0.115 (7)0.176 (10)0.151 (8)0.038 (7)0.037 (6)0.008 (7)
N10.062 (3)0.0256 (17)0.066 (2)0.0060 (17)0.003 (2)0.0065 (16)
O30.058 (2)0.046 (2)0.090 (3)0.0131 (17)0.012 (2)0.0125 (17)
O40.071 (2)0.0302 (16)0.076 (2)0.0034 (15)0.0093 (18)0.0059 (16)
C30.046 (3)0.033 (2)0.066 (3)0.000 (2)0.000 (2)0.008 (2)
C40.054 (3)0.027 (2)0.067 (3)0.003 (2)0.002 (2)0.000 (2)
C50.059 (3)0.054 (3)0.066 (3)0.008 (3)0.006 (3)0.001 (2)
C60.091 (5)0.105 (5)0.077 (4)0.028 (4)0.014 (3)0.015 (4)
C70.112 (5)0.084 (4)0.082 (4)0.011 (4)0.015 (4)0.003 (3)
Geometric parameters (Å, º) top
O1—C11.232 (5)O3—H30.82
O2—C11.225 (6)O4—C31.203 (5)
C1—C21.507 (8)C3—C41.516 (6)
C2—F1A1.280 (8)C4—C51.545 (7)
C2—F31.300 (9)C4—H40.98
C2—F3A1.304 (8)C5—C61.507 (8)
C2—F21.306 (9)C5—C71.512 (8)
C2—F11.348 (8)C5—H50.98
C2—F2A1.351 (8)C6—H6A0.96
N1—C41.487 (6)C6—H6B0.96
N1—H1A0.89C6—H6C0.96
N1—H1B0.89C7—H7A0.96
N1—H1C0.89C7—H7B0.96
O3—C31.300 (6)C7—H7C0.96
O2—C1—O1124.9 (5)N1—C4—C3107.1 (4)
O2—C1—C2117.8 (5)N1—C4—C5110.2 (4)
O1—C1—C2117.2 (4)C3—C4—C5113.1 (4)
F1A—C2—F3A112.0 (10)N1—C4—H4108.8
F3—C2—F2108.4 (11)C3—C4—H4108.8
F3—C2—F1104.6 (11)C5—C4—H4108.8
F2—C2—F1104.3 (11)C6—C5—C7112.8 (5)
F1A—C2—F2A101.1 (9)C6—C5—C4112.9 (4)
F3A—C2—F2A103.1 (9)C7—C5—C4111.4 (5)
F1A—C2—C1115.7 (7)C6—C5—H5106.4
F3—C2—C1117.5 (7)C7—C5—H5106.4
F3A—C2—C1113.2 (7)C4—C5—H5106.4
F2—C2—C1114.0 (8)C5—C6—H6A109.5
F1—C2—C1106.9 (7)C5—C6—H6B109.5
F2A—C2—C1110.2 (6)H6A—C6—H6B109.5
C4—N1—H1A109.5C5—C6—H6C109.5
C4—N1—H1B109.5H6A—C6—H6C109.5
H1A—N1—H1B109.5H6B—C6—H6C109.5
C4—N1—H1C109.5C5—C7—H7A109.5
H1A—N1—H1C109.5C5—C7—H7B109.5
H1B—N1—H1C109.5H7A—C7—H7B109.5
C3—O3—H3109.5C5—C7—H7C109.5
O4—C3—O3125.2 (4)H7A—C7—H7C109.5
O4—C3—C4123.1 (4)H7B—C7—H7C109.5
O3—C3—C4111.7 (4)
O2—C1—C2—F1A36.9 (12)O2—C1—C2—F2A150.8 (9)
O1—C1—C2—F1A142.4 (11)O1—C1—C2—F2A28.5 (10)
O2—C1—C2—F3140.2 (12)O4—C3—C4—N115.5 (7)
O1—C1—C2—F340.4 (12)O3—C3—C4—N1165.7 (4)
O2—C1—C2—F3A94.3 (10)O4—C3—C4—C5106.1 (6)
O1—C1—C2—F3A86.4 (10)O3—C3—C4—C572.6 (5)
O2—C1—C2—F291.4 (13)N1—C4—C5—C671.4 (5)
O1—C1—C2—F287.9 (13)C3—C4—C5—C648.5 (6)
O2—C1—C2—F123.2 (11)N1—C4—C5—C7160.5 (4)
O1—C1—C2—F1157.5 (10)C3—C4—C5—C779.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O2i0.891.872.747 (5)170
N1—H1C···O4ii0.892.022.878 (5)162
O3—H3···O1iii0.821.792.607 (4)174
N1—H1A···O10.891.972.827 (5)161
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z+1.
 

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