From a solution of lithium hydroxide and (
RS)-phenylsuccinic acid in water, crystals of the title compound, Li
+·C
10H
9O
, were obtained. The basic structural feature is an approximately square-planar centrosymmetric Li
2O
2 unit. The Li atoms in this unit are coordinated by further O atoms, yielding a distorted tetrahedral geometry around Li.
Supporting information
CCDC reference: 263558
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (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
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+·C10H9O4− | F(000) = 416 |
Mr = 200.12 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 14.350 (4) Å | θ = 5.2–16.0° |
b = 5.3060 (9) Å | µ = 0.11 mm−1 |
c = 12.672 (5) Å | T = 200 K |
β = 109.96 (2)° | Irregular, colourless |
V = 906.9 (5) Å3 | 0.20 × 0.10 × 0.05 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | Rint = 0.086 |
Radiation source: fine-focus sealed tube | θmax = 24.7°, θmin = 4.5° |
φ and ω scans | h = −16→16 |
6944 measured reflections | k = −4→6 |
1533 independent reflections | l = −14→14 |
1130 reflections with I > 2σ(I) | |
Refinement top
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: difference Fourier map |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.88212 (17) | −0.1731 (5) | 0.36512 (19) | 0.0230 (5) | |
C2 | 0.78350 (16) | −0.2263 (5) | 0.2719 (2) | 0.0255 (6) | |
C3 | 0.78476 (17) | −0.4664 (5) | 0.2077 (2) | 0.0293 (6) | |
C4 | 0.8533 (2) | −0.4553 (5) | 0.1429 (2) | 0.0342 (6) | |
C5 | 0.70464 (17) | −0.2334 (5) | 0.3271 (2) | 0.0286 (6) | |
C6 | 0.63121 (18) | −0.0515 (6) | 0.3024 (2) | 0.0372 (7) | |
C7 | 0.5609 (2) | −0.0547 (6) | 0.3549 (3) | 0.0482 (8) | |
C8 | 0.5639 (2) | −0.2374 (7) | 0.4324 (3) | 0.0487 (9) | |
C9 | 0.6366 (2) | −0.4205 (6) | 0.4580 (2) | 0.0454 (8) | |
C10 | 0.70616 (19) | −0.4176 (6) | 0.4045 (2) | 0.0370 (7) | |
Li | 0.9935 (3) | 0.3086 (9) | 0.4232 (3) | 0.0299 (10) | |
O1 | 0.89720 (12) | 0.0530 (3) | 0.39444 (14) | 0.0297 (5) | |
O2 | 0.93943 (12) | −0.3503 (3) | 0.41067 (13) | 0.0277 (4) | |
O3 | 0.90745 (13) | −0.2800 (4) | 0.14312 (14) | 0.0350 (5) | |
O4A | 0.8770 (7) | −0.6915 (18) | 0.1205 (9) | 0.060 (3) | 0.35 |
O4B | 0.8348 (3) | −0.6400 (10) | 0.0683 (3) | 0.0424 (11) | 0.65 |
H2 | 0.7668 | −0.0822 | 0.2170 | 0.031* | |
H3A | 0.8037 | −0.6137 | 0.2630 | 0.035* | |
H3B | 0.7195 | −0.5084 | 0.1545 | 0.035* | |
H6 | 0.6366 | 0.0792 | 0.2359 | 0.045* | |
H7 | 0.5091 | 0.0761 | 0.3378 | 0.058* | |
H8 | 0.5179 | −0.2335 | 0.4642 | 0.058* | |
H9 | 0.6367 | −0.5505 | 0.5205 | 0.054* | |
H10 | 0.7551 | −0.5579 | 0.4219 | 0.044* | |
H4A | 0.9296 | −0.7801 | 0.1030 | 0.072* | 0.35 |
H4B | 0.8815 | −0.6089 | 0.0319 | 0.051* | 0.65 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0246 (12) | 0.0233 (14) | 0.0239 (12) | −0.0009 (11) | 0.0121 (10) | 0.0008 (11) |
C2 | 0.0225 (12) | 0.0247 (15) | 0.0283 (12) | 0.0005 (10) | 0.0074 (10) | 0.0006 (11) |
C3 | 0.0280 (12) | 0.0320 (16) | 0.0270 (13) | −0.0039 (11) | 0.0081 (10) | −0.0014 (11) |
C4 | 0.0414 (15) | 0.0299 (16) | 0.0342 (15) | −0.0057 (14) | 0.0167 (12) | −0.0062 (13) |
C5 | 0.0235 (12) | 0.0296 (16) | 0.0306 (13) | −0.0048 (11) | 0.0066 (10) | −0.0072 (12) |
C6 | 0.0310 (13) | 0.0333 (17) | 0.0490 (17) | 0.0008 (13) | 0.0158 (12) | −0.0057 (14) |
C7 | 0.0360 (16) | 0.041 (2) | 0.073 (2) | 0.0045 (14) | 0.0257 (15) | −0.0109 (17) |
C8 | 0.0377 (16) | 0.060 (2) | 0.0593 (19) | −0.0127 (16) | 0.0300 (15) | −0.0209 (18) |
C9 | 0.0412 (16) | 0.056 (2) | 0.0432 (17) | −0.0129 (16) | 0.0202 (14) | −0.0048 (15) |
C10 | 0.0302 (13) | 0.0388 (18) | 0.0430 (15) | −0.0011 (13) | 0.0141 (12) | −0.0022 (14) |
Li | 0.027 (2) | 0.031 (3) | 0.030 (2) | 0.0022 (18) | 0.0086 (16) | 0.0016 (19) |
O1 | 0.0325 (9) | 0.0227 (10) | 0.0338 (10) | −0.0019 (8) | 0.0111 (7) | −0.0017 (8) |
O2 | 0.0297 (9) | 0.0233 (10) | 0.0282 (9) | 0.0042 (8) | 0.0073 (7) | 0.0005 (8) |
O3 | 0.0385 (10) | 0.0336 (12) | 0.0373 (11) | −0.0081 (9) | 0.0188 (8) | −0.0046 (9) |
O4A | 0.066 (6) | 0.030 (5) | 0.110 (8) | −0.010 (4) | 0.064 (6) | −0.026 (6) |
O4B | 0.059 (3) | 0.035 (3) | 0.043 (2) | −0.015 (2) | 0.0300 (19) | −0.0126 (19) |
Geometric parameters (Å, º) top
C1—O2 | 1.253 (3) | Li—O3i | 1.940 (4) |
C1—O1 | 1.253 (3) | Li—O2ii | 1.954 (5) |
C1—C2 | 1.528 (3) | Li—O2iii | 2.006 (4) |
C2—C3 | 1.515 (4) | Li—Liiv | 2.776 (9) |
C2—C5 | 1.520 (3) | O4A—O4B | 0.778 (9) |
C3—C4 | 1.482 (3) | C2—H2 | 1.0060 |
C4—O3 | 1.211 (3) | C3—H3A | 1.0226 |
C4—O4B | 1.324 (5) | C3—H3B | 0.9747 |
C4—O4A | 1.354 (10) | C6—H6 | 1.1141 |
C5—C10 | 1.380 (4) | C7—H7 | 0.9857 |
C5—C6 | 1.384 (4) | C8—H8 | 0.8826 |
C6—C7 | 1.386 (4) | C9—H9 | 1.0500 |
C7—C8 | 1.370 (4) | C10—H10 | 0.9949 |
C8—C9 | 1.380 (4) | O4A—H4A | 0.9773 |
C9—C10 | 1.385 (4) | O4B—H4B | 0.949 |
Li—O1 | 1.881 (5) | | |
| | | |
O2—C1—O1 | 124.2 (2) | O2ii—Li—Liiv | 46.27 (14) |
O2—C1—C2 | 120.4 (2) | O2iii—Li—Liiv | 44.73 (12) |
O1—C1—C2 | 115.2 (2) | C1—O1—Li | 142.1 (2) |
C3—C2—C5 | 111.9 (2) | C1—O2—Liv | 155.8 (2) |
C3—C2—C1 | 113.1 (2) | C1—O2—Liiii | 113.90 (19) |
C5—C2—C1 | 106.73 (19) | Liv—O2—Liiii | 88.99 (19) |
C4—C3—C2 | 113.3 (2) | C4—O3—Livi | 138.5 (2) |
O3—C4—O4B | 122.8 (3) | C3—C2—H2 | 108.1 |
O3—C4—O4A | 120.3 (5) | C5—C2—H2 | 107.4 |
O4B—C4—O4A | 33.8 (4) | C1—C2—H2 | 109.4 |
O3—C4—C3 | 125.2 (2) | C4—C3—H3A | 109.8 |
O4B—C4—C3 | 110.9 (3) | C2—C3—H3A | 108.9 |
O4A—C4—C3 | 109.9 (5) | C4—C3—H3B | 106.7 |
C10—C5—C6 | 118.7 (2) | C2—C3—H3B | 112.3 |
C10—C5—C2 | 120.7 (2) | H3A—C3—H3B | 105.5 |
C6—C5—C2 | 120.5 (2) | C5—C6—H6 | 111.2 |
C5—C6—C7 | 120.4 (3) | C7—C6—H6 | 128.3 |
C8—C7—C6 | 120.2 (3) | C8—C7—H7 | 119.5 |
C7—C8—C9 | 120.2 (3) | C6—C7—H7 | 120.3 |
C8—C9—C10 | 119.4 (3) | C7—C8—H8 | 117.7 |
C5—C10—C9 | 121.1 (3) | C9—C8—H8 | 122.1 |
O1—Li—O3i | 109.9 (2) | C8—C9—H9 | 116.5 |
O1—Li—O2ii | 114.0 (2) | C10—C9—H9 | 124.1 |
O3i—Li—O2ii | 121.2 (2) | C5—C10—H10 | 121.7 |
O1—Li—O2iii | 109.9 (2) | C9—C10—H10 | 117.1 |
O3i—Li—O2iii | 108.7 (2) | O4B—O4A—H4A | 114.4 |
O2ii—Li—O2iii | 91.01 (19) | C4—O4A—H4A | 139.6 |
O1—Li—Liiv | 122.2 (3) | C4—O4B—H4A | 102.7 |
O3i—Li—Liiv | 126.7 (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, y−1, z; (vi) −x+2, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4a—H4a···O2vi | 0.98 | 1.98 | 2.918 (4) | 160 |
O4b—H4b···O1vii | 0.95 | 1.86 | 2.686 (4) | 145 |
Symmetry codes: (vi) −x+2, y−1/2, −z+1/2; (vii) x, −y−1/2, z−1/2. |