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From a solution of lithium hydro­xide and (RS)-phenyl­succinic acid in water, crystals of the title compound, Li+·C10H9O{}_{4}^{\,- }, were obtained. The basic structural feature is an approximately square-planar centrosymmetric Li2O2 unit. The Li atoms in this unit are coordinated by further O atoms, yielding a distorted tetrahedral geometry around Li.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001017/hb6138sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001017/hb6138Isup2.hkl
Contains datablock I

CCDC reference: 263558

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.050
  • wR factor = 0.130
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.71 Deg.
Author Response: I happened to set a slightly to low angle in the data collection. (The crystal didn't diffract at all betond 25 degrees in 2 theta). I hope that this is acceptable since the angle appears to be close to the "limit".

Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5884 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.72 Deg. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT351_ALERT_3_C Long C-H Bond (0.96A) C6 - H6 ... 1.11 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 33.80 Deg. O4B -C4 -O4A 1.555 1.555 1.555
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: maXus (Mackay et al., 1999).

Lithium hydrogen (RS)-phenylsuccinate top
Crystal data top
Li+·C10H9O4F(000) = 416
Mr = 200.12Dx = 1.466 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 14.350 (4) Åθ = 5.2–16.0°
b = 5.3060 (9) ŵ = 0.11 mm1
c = 12.672 (5) ÅT = 200 K
β = 109.96 (2)°Irregular, colourless
V = 906.9 (5) Å30.20 × 0.10 × 0.05 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
Rint = 0.086
Radiation source: fine-focus sealed tubeθmax = 24.7°, θmin = 4.5°
φ and ω scansh = 1616
6944 measured reflectionsk = 46
1533 independent reflectionsl = 1414
1130 reflections with I > 2σ(I)
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)] = 0.050Hydrogen site location: difference Fourier map
wR(F2) = 0.130H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.5204P]
where P = (Fo2 + 2Fc2)/3
1533 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.25 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)
C10.88212 (17)0.1731 (5)0.36512 (19)0.0230 (5)
C20.78350 (16)0.2263 (5)0.2719 (2)0.0255 (6)
C30.78476 (17)0.4664 (5)0.2077 (2)0.0293 (6)
C40.8533 (2)0.4553 (5)0.1429 (2)0.0342 (6)
C50.70464 (17)0.2334 (5)0.3271 (2)0.0286 (6)
C60.63121 (18)0.0515 (6)0.3024 (2)0.0372 (7)
C70.5609 (2)0.0547 (6)0.3549 (3)0.0482 (8)
C80.5639 (2)0.2374 (7)0.4324 (3)0.0487 (9)
C90.6366 (2)0.4205 (6)0.4580 (2)0.0454 (8)
C100.70616 (19)0.4176 (6)0.4045 (2)0.0370 (7)
Li0.9935 (3)0.3086 (9)0.4232 (3)0.0299 (10)
O10.89720 (12)0.0530 (3)0.39444 (14)0.0297 (5)
O20.93943 (12)0.3503 (3)0.41067 (13)0.0277 (4)
O30.90745 (13)0.2800 (4)0.14312 (14)0.0350 (5)
O4A0.8770 (7)0.6915 (18)0.1205 (9)0.060 (3)0.35
O4B0.8348 (3)0.6400 (10)0.0683 (3)0.0424 (11)0.65
H20.76680.08220.21700.031*
H3A0.80370.61370.26300.035*
H3B0.71950.50840.15450.035*
H60.63660.07920.23590.045*
H70.50910.07610.33780.058*
H80.51790.23350.46420.058*
H90.63670.55050.52050.054*
H100.75510.55790.42190.044*
H4A0.92960.78010.10300.072*0.35
H4B0.88150.60890.03190.051*0.65
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0246 (12)0.0233 (14)0.0239 (12)0.0009 (11)0.0121 (10)0.0008 (11)
C20.0225 (12)0.0247 (15)0.0283 (12)0.0005 (10)0.0074 (10)0.0006 (11)
C30.0280 (12)0.0320 (16)0.0270 (13)0.0039 (11)0.0081 (10)0.0014 (11)
C40.0414 (15)0.0299 (16)0.0342 (15)0.0057 (14)0.0167 (12)0.0062 (13)
C50.0235 (12)0.0296 (16)0.0306 (13)0.0048 (11)0.0066 (10)0.0072 (12)
C60.0310 (13)0.0333 (17)0.0490 (17)0.0008 (13)0.0158 (12)0.0057 (14)
C70.0360 (16)0.041 (2)0.073 (2)0.0045 (14)0.0257 (15)0.0109 (17)
C80.0377 (16)0.060 (2)0.0593 (19)0.0127 (16)0.0300 (15)0.0209 (18)
C90.0412 (16)0.056 (2)0.0432 (17)0.0129 (16)0.0202 (14)0.0048 (15)
C100.0302 (13)0.0388 (18)0.0430 (15)0.0011 (13)0.0141 (12)0.0022 (14)
Li0.027 (2)0.031 (3)0.030 (2)0.0022 (18)0.0086 (16)0.0016 (19)
O10.0325 (9)0.0227 (10)0.0338 (10)0.0019 (8)0.0111 (7)0.0017 (8)
O20.0297 (9)0.0233 (10)0.0282 (9)0.0042 (8)0.0073 (7)0.0005 (8)
O30.0385 (10)0.0336 (12)0.0373 (11)0.0081 (9)0.0188 (8)0.0046 (9)
O4A0.066 (6)0.030 (5)0.110 (8)0.010 (4)0.064 (6)0.026 (6)
O4B0.059 (3)0.035 (3)0.043 (2)0.015 (2)0.0300 (19)0.0126 (19)
Geometric parameters (Å, º) top
C1—O21.253 (3)Li—O3i1.940 (4)
C1—O11.253 (3)Li—O2ii1.954 (5)
C1—C21.528 (3)Li—O2iii2.006 (4)
C2—C31.515 (4)Li—Liiv2.776 (9)
C2—C51.520 (3)O4A—O4B0.778 (9)
C3—C41.482 (3)C2—H21.0060
C4—O31.211 (3)C3—H3A1.0226
C4—O4B1.324 (5)C3—H3B0.9747
C4—O4A1.354 (10)C6—H61.1141
C5—C101.380 (4)C7—H70.9857
C5—C61.384 (4)C8—H80.8826
C6—C71.386 (4)C9—H91.0500
C7—C81.370 (4)C10—H100.9949
C8—C91.380 (4)O4A—H4A0.9773
C9—C101.385 (4)O4B—H4B0.949
Li—O11.881 (5)
O2—C1—O1124.2 (2)O2ii—Li—Liiv46.27 (14)
O2—C1—C2120.4 (2)O2iii—Li—Liiv44.73 (12)
O1—C1—C2115.2 (2)C1—O1—Li142.1 (2)
C3—C2—C5111.9 (2)C1—O2—Liv155.8 (2)
C3—C2—C1113.1 (2)C1—O2—Liiii113.90 (19)
C5—C2—C1106.73 (19)Liv—O2—Liiii88.99 (19)
C4—C3—C2113.3 (2)C4—O3—Livi138.5 (2)
O3—C4—O4B122.8 (3)C3—C2—H2108.1
O3—C4—O4A120.3 (5)C5—C2—H2107.4
O4B—C4—O4A33.8 (4)C1—C2—H2109.4
O3—C4—C3125.2 (2)C4—C3—H3A109.8
O4B—C4—C3110.9 (3)C2—C3—H3A108.9
O4A—C4—C3109.9 (5)C4—C3—H3B106.7
C10—C5—C6118.7 (2)C2—C3—H3B112.3
C10—C5—C2120.7 (2)H3A—C3—H3B105.5
C6—C5—C2120.5 (2)C5—C6—H6111.2
C5—C6—C7120.4 (3)C7—C6—H6128.3
C8—C7—C6120.2 (3)C8—C7—H7119.5
C7—C8—C9120.2 (3)C6—C7—H7120.3
C8—C9—C10119.4 (3)C7—C8—H8117.7
C5—C10—C9121.1 (3)C9—C8—H8122.1
O1—Li—O3i109.9 (2)C8—C9—H9116.5
O1—Li—O2ii114.0 (2)C10—C9—H9124.1
O3i—Li—O2ii121.2 (2)C5—C10—H10121.7
O1—Li—O2iii109.9 (2)C9—C10—H10117.1
O3i—Li—O2iii108.7 (2)O4B—O4A—H4A114.4
O2ii—Li—O2iii91.01 (19)C4—O4A—H4A139.6
O1—Li—Liiv122.2 (3)C4—O4B—H4A102.7
O3i—Li—Liiv126.7 (3)
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x, y+1, z; (iii) x+2, y, z+1; (iv) x+2, y+1, z+1; (v) x, y1, z; (vi) x+2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4a—H4a···O2vi0.981.982.918 (4)160
O4b—H4b···O1vii0.951.862.686 (4)145
Symmetry codes: (vi) x+2, y1/2, z+1/2; (vii) x, y1/2, z1/2.
 

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