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The structure of potassium benzilate, K+·C14H11O3, previously determined from visually estimated intensities, has been redetermined from CCD data. The K+ ion is five-coordinate and the distribution of O atoms around the metal is a flattened square-base pyramid. Pairs of edge-sharing polyhedra join to form corrugated layers parallel to ab, which stack along the c axis. The K+ ion is in contact with the π electrons of one phenyl ring at a perpendicular distance of 3.0899 (4) Å and is displaced laterally by 0.252 Å with respect to the ring centroid. This interaction and an intramolecular hydrogen bond account for the rigidity of this ring compared to the second ring. The two intramolecular hydrogen bonds present have graph-set motif S(5). An intermolecular hydrogen bond, which also involves the hydroxyl group, has graph-set motif C12(4).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015915/cf6267sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015915/cf6267Isup2.hkl
Contains datablock I

CCDC reference: 221649

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.119
  • Data-to-parameter ratio = 17.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.54 From the CIF: _reflns_number_total 2864 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3116 Completeness (_total/calc) 91.91% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

Potassium α–Hydroxy–α–phenylbenzeneacetate top
Crystal data top
K+·C14H11O3F(000) = 552
Mr = 266.33Dx = 1.439 Mg m3
Dm = 1.428 Mg m3
Dm measured by neutral buoyancy in CHCl3/C4H10O
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3427 reflections
a = 14.1283 (15) Åθ = 1.6–28.5°
b = 9.023 (1) ŵ = 0.43 mm1
c = 10.3639 (11) ÅT = 293 K
β = 111.474 (1)°Plate, colorless
V = 1229.5 (2) Å30.50 × 0.40 × 0.30 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2864 independent reflections
Radiation source: fine-focus sealed tube2213 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 0.70 pixels mm-1θmax = 28.5°, θmin = 1.6°
φ and ω scansh = 1618
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 812
Tmin = 0.757, Tmax = 0.880l = 1313
15415 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0698P)2 + 0.0399P]
where P = (Fo2 + 2Fc2)/3
2864 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.46 e Å3
Special details top

Experimental. Siemens SMART CCD diffractometer equipped with a normal focus, 2.4 kW sealed tube X-ray source (Mo Kα radiation, λ = 0.71073 Å) operating at 30 kV and 20 mA. The data collection covered about 1.3 hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 90, 180 °) for the crystal and each exposure of 12 s covered 0.3° in ω to give a total of 1315 frames. The crystal-to-detector distance was 5.029 cm and the detector swing angle was -30°. Coverage of the unique set was over 99% complete. Crystal decay was monitored by repeating fifty frames from the initial set at the end of the data collection. The analysis of the duplicate reflections indicated that crystal decay was negligible. Unit-cell parameters were determined by a least-squares fit of 3427 reflections in the range 1.55–28.54. Absorption and other corrections were made using a multi-scan technique (SADABS; Sheldrick, 1996)

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*/Ueq
K0.03541 (3)0.03185 (5)0.81633 (4)0.04358 (16)
O10.14873 (10)0.39938 (15)1.06378 (13)0.0367 (3)
H10.1388 (19)0.329 (3)1.108 (3)0.058 (7)*
O20.07919 (10)0.28955 (14)0.79362 (12)0.0382 (3)
O30.07120 (10)0.15646 (15)0.97690 (14)0.0462 (3)
C10.10511 (13)0.26085 (17)0.89388 (17)0.0300 (4)
C20.18665 (12)0.36011 (18)0.91996 (17)0.0294 (4)
C30.28622 (13)0.27359 (19)0.88436 (18)0.0347 (4)
C40.30634 (16)0.1473 (2)0.8034 (2)0.0532 (5)
H40.25860.11290.76820.064*
C50.3969 (2)0.0714 (3)0.7741 (3)0.0743 (8)
H50.40960.01320.71910.089*
C60.46796 (18)0.1198 (4)0.8253 (3)0.0751 (8)
H60.52870.06820.80510.090*
C70.44947 (17)0.2439 (3)0.9061 (3)0.0657 (7)
H70.49740.27620.94180.079*
C80.35905 (15)0.3222 (2)0.9352 (2)0.0486 (5)
H80.34740.40760.98900.058*
C90.20387 (12)0.50445 (18)0.83704 (17)0.0301 (4)
C100.15691 (14)0.6350 (2)0.8976 (2)0.0388 (4)
H100.11500.63590.99080.047*
C110.17182 (17)0.7646 (2)0.8206 (2)0.0479 (5)
H110.14050.85170.86300.057*
C120.23233 (17)0.7654 (2)0.6825 (2)0.0483 (5)
H120.24230.85260.63150.058*
C130.27835 (15)0.6355 (2)0.6199 (2)0.0480 (5)
H130.31850.63490.52600.058*
C140.26491 (14)0.5057 (2)0.69657 (19)0.0389 (4)
H140.29690.41900.65390.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K0.0566 (3)0.0379 (3)0.0456 (3)0.01317 (18)0.0297 (2)0.00574 (18)
O10.0519 (8)0.0315 (7)0.0284 (6)0.0035 (6)0.0167 (5)0.0001 (5)
O20.0497 (7)0.0349 (7)0.0386 (7)0.0045 (5)0.0263 (6)0.0017 (5)
O30.0550 (8)0.0435 (8)0.0480 (8)0.0183 (6)0.0284 (6)0.0164 (6)
C10.0335 (8)0.0260 (8)0.0316 (8)0.0018 (6)0.0132 (7)0.0029 (7)
C20.0324 (8)0.0282 (8)0.0297 (8)0.0009 (6)0.0141 (7)0.0002 (6)
C30.0348 (9)0.0330 (9)0.0375 (9)0.0001 (7)0.0147 (7)0.0072 (7)
C40.0512 (12)0.0523 (13)0.0603 (13)0.0160 (10)0.0255 (10)0.0130 (10)
C50.0633 (15)0.0690 (17)0.0893 (19)0.0314 (13)0.0265 (14)0.0174 (15)
C60.0433 (13)0.081 (2)0.097 (2)0.0201 (12)0.0209 (13)0.0139 (16)
C70.0409 (12)0.0752 (17)0.0907 (18)0.0079 (11)0.0356 (12)0.0222 (15)
C80.0417 (10)0.0468 (12)0.0637 (13)0.0058 (9)0.0271 (9)0.0076 (10)
C90.0315 (8)0.0294 (8)0.0340 (8)0.0030 (6)0.0175 (7)0.0024 (7)
C100.0464 (10)0.0334 (10)0.0387 (9)0.0014 (8)0.0182 (8)0.0007 (8)
C110.0647 (13)0.0293 (10)0.0566 (12)0.0038 (9)0.0304 (11)0.0004 (9)
C120.0598 (12)0.0342 (10)0.0580 (12)0.0089 (9)0.0298 (10)0.0149 (9)
C130.0488 (11)0.0542 (13)0.0401 (10)0.0088 (9)0.0150 (9)0.0141 (9)
C140.0409 (10)0.0359 (10)0.0396 (10)0.0004 (8)0.0142 (8)0.0015 (8)
Geometric parameters (Å, º) top
K—O22.7937 (13)C9—C101.385 (2)
K—O32.8525 (13)C9—C141.394 (2)
K—O1i3.0031 (14)C10—C111.387 (3)
K—O3ii2.6347 (13)C11—C121.373 (3)
K—O2iii2.6414 (13)C12—C131.382 (3)
O1—C21.432 (2)C13—C141.388 (3)
O2—C11.249 (2)O1—H10.77 (2)
O2—Kiv2.6414 (13)C4—H40.930
O3—C11.247 (2)C4—H40.930
O3—Kii2.6347 (13)C5—H50.930
C1—C21.559 (2)C6—H60.930
C2—C91.530 (2)C7—H70.930
C2—C31.531 (2)C8—H80.930
C3—C41.382 (3)C10—H100.930
C3—C81.388 (3)C11—H110.930
C4—C51.384 (3)C12—H120.930
C5—C61.366 (4)C13—H130.930
C6—C71.365 (4)C13—H130.930
C7—C81.393 (3)C14—H140.930
O3ii—K—O2iii79.14 (4)C8—C3—C2119.41 (17)
O3ii—K—O2122.55 (4)C3—C4—C5120.6 (2)
O2iii—K—O2150.761 (19)C6—C5—C4120.6 (3)
O3ii—K—O376.40 (4)C7—C6—C5119.8 (2)
O2iii—K—O3146.61 (4)C6—C7—C8120.2 (2)
O2—K—O346.18 (4)C3—C8—C7120.4 (2)
O3ii—K—O376.40 (4)C10—C9—C14118.48 (16)
O2iii—K—O3146.61 (4)C10—C9—C2121.22 (15)
O2—K—O346.18 (4)C14—C9—C2120.26 (15)
O3ii—K—O1i133.57 (4)C9—C10—C11120.63 (17)
O2iii—K—O1i93.44 (4)C12—C11—C10120.66 (18)
O2—K—O1i57.60 (4)C11—C12—C13119.43 (18)
O3—K—O1i87.31 (4)C12—C13—C14120.31 (18)
O3—K—O1i87.31 (4)C13—C14—C9120.48 (18)
C2—O1—Kv146.43 (10)C2—O1—H1109.2 (19)
C1—O2—Kiv135.80 (11)Kv—O1—H175.1 (18)
C1—O2—K95.43 (10)C3—C4—H4119.7
Kiv—O2—K120.35 (4)C5—C4—H4119.7
C1—O3—Kii163.56 (11)C6—C5—H5119.7
C1—O3—K92.68 (10)C4—C5—H5119.7
Kii—O3—K103.60 (4)C7—C6—H6120.1
O3—C1—O2125.11 (16)C5—C6—H6120.1
O3—C1—O2125.11 (16)C6—C7—H7119.9
O3—C1—C2115.85 (14)C8—C7—H7119.9
O3—C1—C2115.85 (14)C3—C8—H8119.8
O2—C1—C2119.05 (14)C7—C8—H8119.8
O1—C2—C9107.22 (13)C9—C10—H10119.7
O1—C2—C9107.22 (13)C11—C10—H10119.7
O1—C2—C3109.74 (13)C12—C11—H11119.7
O1—C2—C3109.74 (13)C10—C11—H11119.7
C9—C2—C3110.83 (13)C11—C12—H12120.3
O1—C2—C1107.70 (13)C13—C12—H12120.3
O1—C2—C1107.70 (13)C12—C13—H13119.8
C9—C2—C1111.55 (13)C14—C13—H13119.8
C3—C2—C1109.71 (13)C13—C14—H14119.8
C4—C3—C8118.35 (18)C9—C14—H14119.8
C4—C3—C2122.24 (16)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y, z+2; (iii) x, y1/2, z+3/2; (iv) x, y+1/2, z+3/2; (v) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2v0.77 (2)2.09 (2)2.7986 (18)154 (2)
O1—H1···O30.77 (2)2.47 (3)2.7454 (18)103 (2)
C10—H10···O10.932.372.712 (2)101
Symmetry code: (v) x, y+1/2, z+1/2.
 

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