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The title compound, (6,7,9,10,12,13,15,16-octa­hydro­dibenzo[b,e]-1,4,7,10,13,16-hexa­oxacyclo­octa­decine)­potassium chloro­chromate, [K(C20H24O6)][CrClO3], is the complex formed by a K+ cation with one crown ether mol­ecule and a chloro­chromate anion. The cation is displaced from the mean plane of the ether O atoms by 0.849 (2) Å towards the anion. It forms coordination bonds with all of the O atoms of the crown ether, as well as with the disordered O and Cl atoms of the anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030151/hb6269sup1.cif
Contains datablocks global, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030151/hb6269IVsup2.hkl
Contains datablock IV

CCDC reference: 287569

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in main residue
  • R factor = 0.068
  • wR factor = 0.197
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O8 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O9 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Cr1
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.84 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for K1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

There are three possible isomers of dibenzo-18-crown-6, namely [3.3]dibenzo-18-crown-6, (I), [2.4]dibenzo-18-crown-6, (II) and [1.5]dibenzo-18-crown-6, (III), which differ in terms of the positions of the aromatic rings. With regard to the ability of these crown ether (CE) molecules to form complexes with cations and neutral guest molecules, the [1.5]dibenzo-18-crown-6 molecule, (III), is, in our opinion, the most interesting. In particular, it has the minimum distance between benzene rings of only one bridging O atom. Restricted rotation around the Car—O bonds may result in selectivity in complex formation, which was recently confirmed by us (Kotlyar, Fonari et al., 2005; Ganin et al., 2005).

We now report the crystal structure of the title complex, (IV), of [1.5]dibenzo-18-crown-6 with potassium chlorochromate (Fig. 1), obtained by mixing KCrO3Cl and CE ethyl acetate solutions in a 1:1 ratio at room temperature.

The CE molecule in (IV) possesses the crown-like conformation, which is somewhat strained due to the presence of the two benzene rings. The C1—O1 and C20—O1 bonds are geometrically non-equivalent. The C20—O1—C1—C2 torsion angle of 3.9 (7)° implies the existence of electronic conjugation between the lone pairs of the O atom and the π system of the C1–C6 ring. The C1—O1 bond has a syn-clinal conformation with respect to the C15–C20 benzene ring [C1—O1—C20—C19 = 72.1 (6)°], so the conjugation of this ring with the lone pairs of atom O1 is disrupted. Nevertheless, the C1—O1 and C20—O1 bond lengths are practically the same (Table 1). This could be caused by elongation of the C1—O1 bond due to the presence of a short C20···H2 intramolecular contact of 2.54 Å (van der Waals radius sum for C and H = 2.86 Å; Zefirov & Zorky, 1989). The C2—C1—C20—C19 pseudo-dihedral angle in (IV) of 62.3 (5)° is somewhat smaller than that in the free [1.5]dibenzo-18-crown-6 ligand (89.3°; Kotlyar, Fonari et al., 2005). Based on this fact, we can suggest that the complexation probably leads to some flattening of the Ar–O–Ar fragment.

The K+ cation is coordinated by all six O atoms of the CE molecule. The K—O(ether) bond distances are within the range 2.744 (4)–2.975 (4) Å (Table 1). The bridging O atom between the benzene rings, O1, lies opposite atom O4. The cation is shifted from the mean plane of the CE O atoms by 0.849 (2) Å toward the anion, due to the formation of bonds with the anion.

The anion is disordered over two positions [occupancy ratio 0.729 (8):0.271 (8)] as a result of rotation around the bisector of the O7—Cr1—O9 bond angle. The minor disorder component of Cl1 (marked Cl1' in Fig. 1) lies near atom O8, and consequently atom O8' lies near atom Cl1. In contrast with previously reported structures of CE complexes with potassium chlorochromate (Kotlyar, Zubatyuk, Shishkin et al., 2004; Kotlyar, Zubatyuk, Zhygalko et al., 2004; Kotlyar, Fonari et al., 2005 or Kotlyar, Zubatyuk et al., 2005?), the Cl atom of the anion also participates in the formation of complex (IV).

Experimental top

To a stirred solution of potassium chlorochromate (241 mg, 1.38 mmol) in dry ethyl acetate (10 ml) at room temperature was added a solution of [1.5]dibenzo-18-crown-6 (497 mg, 1.38 mmol) in dry ethyl acetate (7 ml). The reaction mixture was stirred for 10 min and the yellow–orange precipitate which formed was filtered off, washed with cold ethyl acetate (2 ml) and diethyl ether (2 ml), dried at reduced pressure and heated at 313 K to constant weight (yield 65%, 480 mg). Transparent yellow crystals of (IV), suitable for X-ray investigation [m.p. 417–420 K (decomposition)] were obtained by evaporation of a dichloromethane solution. Analysis, calculated for C20H24O9ClCrK: C 44.90, H 4.52, Cl 6.63, Cr 9.72%; found: C 44.99, H 4.38, Cl 6.56, Cr 9.60%. The crystals are soluble in dichloromethane, dimethyl sulfoxide, dimethyl formamide and acetone, and sparingly soluble in chloroform.

Refinement top

The disordered atoms which occupy neighbouring sites (O8' and Cl1, and O8 and Cl1') were constrained to have the same Uij components and their site occupancies were constrained to sum to unity. The Cr1—O8 and Cr1—O8' bond lengths were restrained to 1.59 (1) Å. All H atoms were placed in calculated positions and included in the refnement in the riding-model approximation, with C—H distances in the range 0.97–0.98 Å and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: P3/PC (Siemens, 1989); cell refinement: P3/PC; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of (IV), with displacement ellipsoids drawn at the 50% probability level. The minor disorder component of the anion is indicated by primed atoms.
(6,7,9,10,12,13,15,16- octahydrodibenzo[b,e][1,4,7,10,13,16] hexaoxacyclooctadecine)potassium chlorochromate top
Crystal data top
[K(C20H24O6)][CrClO3]Z = 2
Mr = 534.94F(000) = 552
Triclinic, P1Dx = 1.490 Mg m3
Hall symbol: -P 1Melting point: 417 K
a = 10.139 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.649 (4) ÅCell parameters from 24 reflections
c = 12.138 (3) Åθ = 12–16°
α = 95.34 (3)°µ = 0.81 mm1
β = 94.11 (2)°T = 295 K
γ = 113.05 (2)°Block, yellow
V = 1192.3 (7) Å30.30 × 0.20 × 0.20 mm
Data collection top
Siemens P3/PC
diffractometer
Rint = 0.069
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 1.7°
Graphite monochromatorh = 012
θ/2θ scansk = 1211
4317 measured reflectionsl = 1414
4067 independent reflections2 standard reflections every 98 reflections
2703 reflections with I > 2σ(I) intensity decay: 3%
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1033P)2 + 1.1342P]
where P = (Fo2 + 2Fc2)/3
4067 reflections(Δ/σ)max = 0.003
296 parametersΔρmax = 0.76 e Å3
2 restraintsΔρmin = 0.39 e Å3
Crystal data top
[K(C20H24O6)][CrClO3]γ = 113.05 (2)°
Mr = 534.94V = 1192.3 (7) Å3
Triclinic, P1Z = 2
a = 10.139 (3) ÅMo Kα radiation
b = 10.649 (4) ŵ = 0.81 mm1
c = 12.138 (3) ÅT = 295 K
α = 95.34 (3)°0.30 × 0.20 × 0.20 mm
β = 94.11 (2)°
Data collection top
Siemens P3/PC
diffractometer
Rint = 0.069
4317 measured reflections2 standard reflections every 98 reflections
4067 independent reflections intensity decay: 3%
2703 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0682 restraints
wR(F2) = 0.197H-atom parameters constrained
S = 1.04Δρmax = 0.76 e Å3
4067 reflectionsΔρmin = 0.39 e Å3
296 parameters
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)
Cl10.5525 (4)0.1504 (6)0.5885 (3)0.1460 (18)0.729 (8)
O80.4662 (15)0.3387 (14)0.7385 (15)0.104 (2)0.729 (8)
O8'0.607 (3)0.204 (4)0.6318 (13)0.1460 (18)0.271 (8)
Cl1'0.4607 (17)0.3847 (15)0.7242 (17)0.104 (2)0.271 (8)
Cr10.55972 (10)0.24649 (10)0.74816 (9)0.0804 (4)
K10.20725 (11)0.14150 (11)0.81423 (9)0.0561 (3)
O10.1217 (4)0.1193 (3)0.7012 (3)0.0617 (9)
O20.0312 (3)0.0115 (3)0.6384 (2)0.0515 (8)
O30.0070 (4)0.2567 (3)0.7651 (3)0.0606 (9)
O40.2200 (5)0.3702 (5)0.9467 (4)0.1040 (16)
O50.2414 (4)0.1445 (4)1.0448 (3)0.0709 (10)
O60.1958 (3)0.1054 (3)0.9163 (3)0.0594 (8)
O70.7201 (5)0.3310 (5)0.8044 (6)0.1233 (19)
O90.4772 (5)0.1297 (5)0.8221 (5)0.1136 (17)
C10.0168 (5)0.2010 (5)0.6513 (4)0.0493 (10)
C20.0745 (6)0.3412 (5)0.6371 (4)0.0656 (13)
H2A0.02110.38860.66270.079*
C30.2147 (7)0.4130 (6)0.5839 (5)0.0834 (18)
H3A0.25470.50870.57350.100*
C40.2927 (6)0.3433 (7)0.5472 (6)0.0865 (18)
H4A0.38570.39180.51120.104*
C50.2355 (5)0.2021 (6)0.5627 (4)0.0665 (14)
H5A0.28990.15570.53680.080*
C60.0977 (5)0.1282 (5)0.6167 (4)0.0478 (10)
C70.1178 (5)0.0868 (5)0.6123 (4)0.0596 (12)
H7A0.20300.05680.65120.071*
H7B0.14860.07050.53290.071*
C80.0287 (6)0.2356 (6)0.6477 (4)0.0649 (13)
H8A0.05870.26450.61140.078*
H8B0.08220.28960.62690.078*
C90.0641 (6)0.3971 (5)0.8105 (5)0.0725 (15)
H9A0.00880.43360.79840.087*
H9B0.14620.44890.77340.087*
C100.1093 (7)0.4120 (6)0.9300 (5)0.0776 (16)
H10A0.14060.50740.96190.093*
H10B0.02840.35680.96670.093*
C110.2769 (9)0.3792 (8)1.0587 (6)0.104 (2)
H11A0.26030.45041.10380.125*
H11B0.38040.40601.06220.125*
C120.2119 (7)0.2475 (8)1.1063 (5)0.091 (2)
H12A0.25270.26051.18330.109*
H12B0.10850.22031.10450.109*
C130.1984 (7)0.0204 (7)1.0887 (5)0.0880 (19)
H13A0.09390.02481.07960.106*
H13B0.23210.03741.16770.106*
C140.2589 (7)0.0697 (6)1.0304 (4)0.0787 (18)
H14A0.36290.02201.03430.094*
H14B0.23770.15231.06580.094*
C150.2535 (5)0.1726 (5)0.8458 (4)0.0537 (12)
C160.3499 (6)0.2289 (6)0.8784 (6)0.0755 (17)
H16A0.37810.22500.95360.091*
C170.4037 (6)0.2901 (7)0.7997 (7)0.089 (2)
H17A0.46750.32860.82260.107*
C180.3666 (8)0.2962 (7)0.6899 (7)0.097 (2)
H18A0.40600.33640.63770.116*
C190.2695 (7)0.2421 (6)0.6557 (5)0.0807 (17)
H19A0.24310.24580.58010.097*
C200.2119 (5)0.1826 (5)0.7335 (4)0.0577 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.121 (3)0.265 (5)0.076 (2)0.114 (3)0.0048 (16)0.010 (2)
O80.093 (3)0.089 (8)0.154 (6)0.054 (4)0.022 (3)0.039 (6)
O8'0.121 (3)0.265 (5)0.076 (2)0.114 (3)0.0048 (16)0.010 (2)
Cl1'0.093 (3)0.089 (8)0.154 (6)0.054 (4)0.022 (3)0.039 (6)
Cr10.0608 (6)0.0776 (7)0.1049 (8)0.0287 (5)0.0013 (5)0.0246 (6)
K10.0531 (6)0.0621 (6)0.0551 (6)0.0281 (5)0.0007 (5)0.0002 (5)
O10.073 (2)0.0586 (19)0.059 (2)0.0409 (18)0.0250 (17)0.0041 (15)
O20.0516 (17)0.0592 (19)0.0512 (18)0.0310 (15)0.0032 (14)0.0109 (14)
O30.077 (2)0.054 (2)0.059 (2)0.0333 (17)0.0035 (17)0.0158 (16)
O40.125 (4)0.126 (4)0.081 (3)0.086 (3)0.024 (3)0.025 (3)
O50.077 (2)0.084 (3)0.0461 (19)0.027 (2)0.0114 (17)0.0056 (18)
O60.0578 (19)0.067 (2)0.0475 (18)0.0199 (17)0.0085 (15)0.0111 (16)
O70.067 (3)0.091 (3)0.191 (6)0.018 (2)0.013 (3)0.004 (3)
O90.078 (3)0.114 (4)0.159 (5)0.038 (3)0.012 (3)0.073 (3)
C10.053 (3)0.059 (3)0.038 (2)0.026 (2)0.0011 (19)0.007 (2)
C20.084 (4)0.060 (3)0.058 (3)0.034 (3)0.004 (3)0.014 (2)
C30.083 (4)0.058 (3)0.091 (4)0.009 (3)0.009 (3)0.009 (3)
C40.052 (3)0.079 (4)0.109 (5)0.011 (3)0.006 (3)0.001 (4)
C50.051 (3)0.079 (4)0.069 (3)0.026 (3)0.003 (2)0.009 (3)
C60.054 (3)0.054 (3)0.039 (2)0.025 (2)0.0064 (19)0.0105 (19)
C70.066 (3)0.079 (4)0.051 (3)0.047 (3)0.002 (2)0.018 (2)
C80.079 (3)0.076 (4)0.057 (3)0.046 (3)0.010 (3)0.025 (3)
C90.078 (4)0.056 (3)0.088 (4)0.030 (3)0.006 (3)0.015 (3)
C100.090 (4)0.063 (3)0.087 (4)0.041 (3)0.010 (3)0.000 (3)
C110.125 (6)0.108 (6)0.081 (5)0.066 (5)0.029 (4)0.032 (4)
C120.080 (4)0.133 (6)0.050 (3)0.042 (4)0.004 (3)0.029 (4)
C130.094 (4)0.100 (5)0.048 (3)0.014 (4)0.013 (3)0.018 (3)
C140.096 (4)0.071 (4)0.049 (3)0.014 (3)0.015 (3)0.022 (3)
C150.044 (2)0.048 (3)0.063 (3)0.013 (2)0.009 (2)0.014 (2)
C160.063 (3)0.061 (3)0.094 (4)0.021 (3)0.025 (3)0.021 (3)
C170.062 (4)0.081 (4)0.130 (6)0.040 (3)0.016 (4)0.016 (4)
C180.097 (5)0.094 (5)0.126 (6)0.067 (4)0.019 (4)0.008 (4)
C190.099 (4)0.087 (4)0.074 (4)0.058 (4)0.002 (3)0.011 (3)
C200.061 (3)0.055 (3)0.062 (3)0.032 (2)0.007 (2)0.006 (2)
Geometric parameters (Å, º) top
Cr1—Cl12.088 (4)C4—H4A0.9300
Cr1—O81.617 (8)C5—C61.383 (7)
Cr1—O8'1.605 (10)C5—H5A0.9300
Cr1—Cl1'2.110 (11)C7—C81.486 (7)
Cr1—O71.581 (5)C7—H7A0.9700
Cr1—O91.597 (5)C7—H7B0.9700
K1—O12.753 (3)C8—H8A0.9700
K1—O22.899 (3)C8—H8B0.9700
K1—O32.810 (3)C9—C101.464 (8)
K1—O42.744 (4)C9—H9A0.9700
K1—O52.791 (4)C9—H9B0.9700
K1—O62.975 (4)C10—H10A0.9700
K1—O82.922 (15)C10—H10B0.9700
K1—O92.784 (5)C11—C121.489 (10)
K1—Cl1'3.197 (14)C11—H11A0.9700
C1—O11.385 (5)C11—H11B0.9700
C20—O11.388 (5)C12—H12A0.9700
O2—C61.362 (5)C12—H12B0.9700
O2—C71.439 (5)C13—C141.480 (9)
O3—C91.413 (6)C13—H13A0.9700
O3—C81.419 (6)C13—H13B0.9700
O4—C101.369 (7)C14—H14A0.9700
O4—C111.417 (8)C14—H14B0.9700
O5—C131.390 (7)C15—C201.379 (7)
O5—C121.409 (7)C15—C161.385 (7)
O6—C151.368 (6)C16—C171.368 (9)
O6—C141.434 (6)C16—H16A0.9300
C1—C21.361 (7)C17—C181.348 (10)
C1—C61.400 (6)C17—H17A0.9300
C2—C31.395 (8)C18—C191.379 (9)
C2—H2A0.9300C18—H18A0.9300
C3—C41.358 (9)C19—C201.375 (8)
C3—H3A0.9300C19—H19A0.9300
C4—C51.371 (8)
Cr1—O8—K195.8 (5)O1—C1—C6114.7 (4)
Cr1—Cl1'—K179.1 (4)C1—C2—C3119.4 (5)
O7—Cr1—O9109.4 (3)C1—C2—H2A120.3
O7—Cr1—O8'94.1 (11)C3—C2—H2A120.3
O9—Cr1—O8'119.6 (14)C4—C3—C2120.1 (5)
O7—Cr1—O8113.6 (6)C4—C3—H3A119.9
O9—Cr1—O8106.1 (6)C2—C3—H3A119.9
O8'—Cr1—O8113.8 (13)C3—C4—C5120.6 (5)
O7—Cr1—Cl1111.9 (3)C3—C4—H4A119.7
O9—Cr1—Cl1107.9 (3)C5—C4—H4A119.7
O8'—Cr1—Cl118.1 (12)C4—C5—C6120.6 (5)
O8—Cr1—Cl1107.7 (7)C4—C5—H5A119.7
O7—Cr1—Cl1'108.8 (5)C6—C5—H5A119.7
O9—Cr1—Cl1'113.9 (5)O2—C6—C5125.6 (4)
O8'—Cr1—Cl1'108.9 (13)O2—C6—C1116.1 (4)
O8—Cr1—Cl1'7.9 (9)C5—C6—C1118.3 (4)
Cl1—Cr1—Cl1'104.9 (6)O2—C7—C8108.1 (4)
O4—K1—O1164.36 (15)O2—C7—H7A110.1
O4—K1—O9110.88 (17)C8—C7—H7A110.1
O1—K1—O982.04 (14)O2—C7—H7B110.1
O4—K1—O562.08 (13)C8—C7—H7B110.1
O1—K1—O5112.23 (12)H7A—C7—H7B108.4
O9—K1—O585.03 (15)O3—C8—C7108.5 (4)
O4—K1—O360.20 (12)O3—C8—H8A110.0
O1—K1—O3111.63 (10)C7—C8—H8A110.0
O9—K1—O3154.65 (12)O3—C8—H8B110.0
O5—K1—O3107.59 (11)C7—C8—H8B110.0
O4—K1—O2118.11 (12)H8A—C8—H8B108.4
O1—K1—O254.19 (9)O3—C9—C10110.1 (4)
O9—K1—O2127.03 (15)O3—C9—H9A109.3
O5—K1—O2135.09 (11)C10—C9—H9A109.8
O3—K1—O258.15 (9)O3—C9—H9B109.9
O4—K1—O883.1 (3)C10—C9—H9B109.5
O1—K1—O8112.3 (3)H9A—C9—H9B108.2
O9—K1—O853.43 (18)O4—C10—C9109.9 (5)
O5—K1—O8111.3 (4)O4—C10—H10A109.7
O3—K1—O8101.22 (18)C9—C10—H10A109.7
O2—K1—O8113.2 (4)O4—C10—H10B109.7
O4—K1—O6119.89 (13)C9—C10—H10B109.7
O1—K1—O654.71 (9)H10A—C10—H10B108.2
O9—K1—O670.69 (12)O4—C11—C12113.0 (6)
O5—K1—O658.20 (11)O4—C11—H11A109.0
O3—K1—O6134.66 (10)C12—C11—H11A109.0
O2—K1—O699.63 (9)O4—C11—H11B109.0
O8—K1—O6124.12 (18)C12—C11—H11B109.0
O4—K1—Cl1'77.7 (4)H11A—C11—H11B107.8
O1—K1—Cl1'117.1 (4)O5—C12—C11109.7 (5)
O9—K1—Cl1'62.4 (2)O5—C12—H12A109.5
O5—K1—Cl1'114.0 (4)C11—C12—H12A109.3
O3—K1—Cl1'92.2 (2)O5—C12—H12B110.3
O2—K1—Cl1'109.2 (4)C11—C12—H12B109.9
O8—K1—Cl1'9.0 (3)H12A—C12—H12B108.1
O6—K1—Cl1'133.1 (2)O5—C13—C14109.7 (5)
O4—K1—Cr1101.85 (12)O5—C13—H13A109.7
O1—K1—Cr193.59 (9)C14—C13—H13A109.7
O9—K1—Cr126.70 (10)O5—C13—H13B109.7
O5—K1—Cr1102.81 (9)C14—C13—H13B109.7
O3—K1—Cr1128.18 (8)H13A—C13—H13B108.2
O2—K1—Cr1119.41 (8)O6—C14—C13108.8 (5)
O8—K1—Cr127.52 (15)O6—C14—H14A109.9
O6—K1—Cr197.02 (8)C13—C14—H14A109.9
Cl1'—K1—Cr136.5 (2)O6—C14—H14B109.9
C1—O1—C20118.6 (4)C13—C14—H14B109.9
C1—O1—K1125.2 (3)H14A—C14—H14B108.3
C20—O1—K1112.1 (3)O6—C15—C20116.2 (4)
C6—O2—C7116.5 (4)O6—C15—C16125.3 (5)
C6—O2—K1120.4 (2)C20—C15—C16118.5 (5)
C7—O2—K1117.1 (3)C17—C16—C15120.0 (6)
C9—O3—C8113.0 (4)C17—C16—H16A120.0
C9—O3—K1110.1 (3)C15—C16—H16A120.0
C8—O3—K1108.0 (3)C18—C17—C16121.6 (6)
C10—O4—C11116.9 (5)C18—C17—H17A119.2
C10—O4—K1118.1 (4)C16—C17—H17A119.2
C11—O4—K1113.2 (4)C17—C18—C19119.4 (7)
C13—O5—C12114.7 (5)C17—C18—H18A120.3
C13—O5—K1119.3 (3)C19—C18—H18A120.3
C12—O5—K1114.4 (4)C20—C19—C18119.9 (6)
C15—O6—C14116.9 (4)C20—C19—H19A120.0
C15—O6—K1106.2 (2)C18—C19—H19A120.0
C14—O6—K1111.5 (3)C19—C20—C15120.6 (5)
Cr1—O9—K1101.8 (2)C19—C20—O1120.9 (5)
C2—C1—O1124.4 (4)C15—C20—O1118.1 (4)
C2—C1—C6120.9 (4)
K1—O8—Cr1—O7135.5 (4)O8—K1—O5—C13134.6 (4)
K1—O8—Cr1—O915.2 (7)O6—K1—O5—C1316.8 (4)
K1—O8—Cr1—O8'118.4 (15)Cl1'—K1—O5—C13143.9 (5)
K1—O8—Cr1—Cl1100.1 (5)Cr1—K1—O5—C13107.1 (4)
K1—O8—Cr1—Cl1'170 (9)O4—K1—O5—C1214.8 (4)
K1—Cl1'—Cr1—O7137.2 (3)O1—K1—O5—C12149.1 (4)
K1—Cl1'—Cr1—O914.8 (6)O9—K1—O5—C12131.6 (4)
K1—Cl1'—Cr1—O8'121.5 (13)O3—K1—O5—C1225.9 (4)
K1—Cl1'—Cr1—O89 (8)O2—K1—O5—C1288.2 (4)
K1—Cl1'—Cr1—Cl1103.0 (3)O8—K1—O5—C1284.1 (4)
Cr1—O8—K1—O4132.9 (7)O6—K1—O5—C12158.1 (4)
Cr1—O8—K1—O150.3 (8)Cl1'—K1—O5—C1274.7 (5)
Cr1—O8—K1—O910.4 (5)Cr1—K1—O5—C12111.5 (4)
Cr1—O8—K1—O576.5 (8)O4—K1—O6—C15153.7 (3)
Cr1—O8—K1—O3169.4 (6)O1—K1—O6—C1543.8 (2)
Cr1—O8—K1—O2109.5 (7)O9—K1—O6—C1550.1 (3)
Cr1—O8—K1—O611.2 (10)O5—K1—O6—C15146.4 (3)
Cr1—O8—K1—Cl1'175 (5)O3—K1—O6—C15130.1 (3)
Cr1—Cl1'—K1—O4130.4 (6)O2—K1—O6—C1575.9 (3)
Cr1—Cl1'—K1—O155.0 (6)O8—K1—O6—C1550.9 (5)
Cr1—Cl1'—K1—O98.7 (4)Cl1'—K1—O6—C1552.1 (6)
Cr1—Cl1'—K1—O578.9 (6)Cr1—K1—O6—C1545.7 (3)
Cr1—Cl1'—K1—O3170.8 (5)O4—K1—O6—C1425.2 (4)
Cr1—Cl1'—K1—O2113.8 (5)O1—K1—O6—C14172.2 (4)
Cr1—Cl1'—K1—O84 (4)O9—K1—O6—C1478.3 (4)
Cr1—Cl1'—K1—O610.8 (9)O5—K1—O6—C1417.9 (4)
O4—K1—O1—C138.5 (6)O3—K1—O6—C14101.5 (4)
O9—K1—O1—C1174.8 (3)O2—K1—O6—C14155.7 (4)
O5—K1—O1—C1103.9 (3)O8—K1—O6—C1477.6 (6)
O3—K1—O1—C117.0 (3)Cl1'—K1—O6—C1476.4 (6)
O2—K1—O1—C126.5 (3)Cr1—K1—O6—C1482.8 (4)
O8—K1—O1—C1129.8 (4)O7—Cr1—O9—K1139.2 (3)
O6—K1—O1—C1113.3 (3)O8'—Cr1—O9—K1114.1 (11)
Cl1'—K1—O1—C1121.4 (4)O8—Cr1—O9—K116.3 (7)
Cr1—K1—O1—C1150.7 (3)Cl1—Cr1—O9—K198.9 (2)
O4—K1—O1—C20118.3 (5)Cl1'—Cr1—O9—K117.1 (7)
O9—K1—O1—C2028.4 (3)O4—K1—O9—Cr174.4 (3)
O5—K1—O1—C2052.9 (3)O1—K1—O9—Cr1114.7 (3)
O3—K1—O1—C20173.7 (3)O5—K1—O9—Cr1132.0 (3)
O2—K1—O1—C20176.7 (3)O3—K1—O9—Cr110.3 (6)
O8—K1—O1—C2073.4 (4)O2—K1—O9—Cr182.5 (3)
O6—K1—O1—C2043.5 (3)O8—K1—O9—Cr110.7 (5)
Cl1'—K1—O1—C2081.8 (4)O6—K1—O9—Cr1170.1 (3)
Cr1—K1—O1—C2052.5 (3)Cl1'—K1—O9—Cr111.6 (5)
O4—K1—O2—C6139.6 (3)K1—O1—C1—C2151.5 (4)
O1—K1—O2—C624.3 (3)C20—O1—C1—C6177.1 (4)
O9—K1—O2—C665.0 (3)K1—O1—C1—C627.5 (5)
O5—K1—O2—C662.1 (3)O1—C1—C2—C3178.9 (5)
O3—K1—O2—C6145.2 (3)C6—C1—C2—C32.2 (8)
O8—K1—O2—C6125.8 (3)C1—C2—C3—C40.4 (9)
O6—K1—O2—C68.0 (3)C2—C3—C4—C50.5 (10)
Cl1'—K1—O2—C6134.5 (4)C3—C4—C5—C60.4 (10)
Cr1—K1—O2—C695.8 (3)C7—O2—C6—C56.3 (6)
O4—K1—O2—C712.3 (3)K1—O2—C6—C5158.4 (4)
O1—K1—O2—C7176.2 (3)C7—O2—C6—C1174.6 (4)
O9—K1—O2—C7143.1 (3)K1—O2—C6—C122.6 (5)
O5—K1—O2—C789.8 (3)C4—C5—C6—O2178.7 (5)
O3—K1—O2—C76.6 (3)C4—C5—C6—C12.2 (8)
O8—K1—O2—C782.4 (4)C2—C1—C6—O2177.7 (4)
O6—K1—O2—C7143.9 (3)C2—C1—C6—C53.1 (7)
Cl1'—K1—O2—C773.7 (4)O1—C1—C6—C5177.9 (4)
Cr1—K1—O2—C7112.4 (3)C6—O2—C7—C8176.9 (4)
O4—K1—O3—C923.8 (3)K1—O2—C7—C823.9 (5)
O1—K1—O3—C9171.0 (3)C9—O3—C8—C7167.0 (4)
O9—K1—O3—C951.7 (5)K1—O3—C8—C771.0 (4)
O5—K1—O3—C965.4 (3)C8—O3—C9—C10175.4 (5)
O2—K1—O3—C9161.9 (3)K1—O3—C9—C1054.6 (5)
O8—K1—O3—C951.4 (5)C11—O4—C10—C9179.6 (6)
O6—K1—O3—C9127.8 (3)K1—O4—C10—C939.8 (6)
Cl1'—K1—O3—C950.6 (5)C10—O4—C11—C1295.3 (7)
Cr1—K1—O3—C957.6 (3)K1—O4—C11—C1247.1 (7)
O4—K1—O3—C8147.6 (3)C13—O5—C12—C11173.8 (5)
O1—K1—O3—C847.2 (3)K1—O5—C12—C1143.1 (6)
O9—K1—O3—C872.1 (5)C12—O5—C13—C14169.4 (5)
O5—K1—O3—C8170.8 (3)K1—O5—C13—C1449.4 (6)
O2—K1—O3—C838.1 (3)C15—O6—C14—C13171.2 (4)
O8—K1—O3—C872.4 (5)K1—O6—C14—C1348.7 (5)
O6—K1—O3—C8108.4 (3)C14—O6—C15—C20167.8 (4)
Cl1'—K1—O3—C873.2 (5)K1—O6—C15—C2042.6 (4)
Cr1—K1—O3—C866.2 (3)C14—O6—C15—C1611.4 (7)
O1—K1—O4—C1053.0 (7)K1—O6—C15—C16136.7 (4)
O9—K1—O4—C10162.6 (4)O6—C15—C16—C17178.0 (5)
O5—K1—O4—C10125.2 (5)C20—C15—C16—C171.2 (8)
O3—K1—O4—C109.0 (4)C15—C16—C17—C180.8 (10)
O2—K1—O4—C103.5 (5)C16—C17—C18—C191.5 (11)
O8—K1—O4—C10116.2 (5)C17—C18—C19—C200.1 (10)
O6—K1—O4—C10118.2 (4)C18—C19—C20—C152.0 (9)
Cl1'—K1—O4—C10108.8 (5)C18—C19—C20—O1175.6 (5)
Cr1—K1—O4—C10136.4 (4)O6—C15—C20—C19176.7 (5)
O1—K1—O4—C1189.0 (6)C16—C15—C20—C192.6 (8)
O9—K1—O4—C1155.4 (5)C16—C15—C20—O1176.4 (4)
O5—K1—O4—C1116.7 (5)K1—O1—C20—C19129.4 (5)
O3—K1—O4—C11150.9 (6)C1—O1—C20—C15114.1 (5)
O2—K1—O4—C11145.4 (5)K1—O1—C20—C1544.4 (5)
O8—K1—O4—C11101.9 (6)O1—C1—C6—O21.3 (6)
O6—K1—O4—C1123.7 (6)O2—C7—C8—O363.3 (5)
Cl1'—K1—O4—C11109.2 (6)O3—C9—C10—O464.3 (7)
Cr1—K1—O4—C1181.6 (5)O4—C11—C12—O561.6 (7)
O4—K1—O5—C13156.1 (5)O5—C13—C14—O665.5 (6)
O1—K1—O5—C137.8 (4)O6—C15—C20—O12.9 (6)
O9—K1—O5—C1387.1 (4)C20—O1—C1—C23.9 (7)
O3—K1—O5—C13115.4 (4)C1—O1—C20—C1972.1 (6)
O2—K1—O5—C1353.2 (5)

Experimental details

Crystal data
Chemical formula[K(C20H24O6)][CrClO3]
Mr534.94
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)10.139 (3), 10.649 (4), 12.138 (3)
α, β, γ (°)95.34 (3), 94.11 (2), 113.05 (2)
V3)1192.3 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.81
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerSiemens P3/PC
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4317, 4067, 2703
Rint0.069
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.197, 1.04
No. of reflections4067
No. of parameters296
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.76, 0.39

Computer programs: P3/PC (Siemens, 1989), P3/PC, XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
K1—O12.753 (3)K1—O82.922 (15)
K1—O22.899 (3)K1—O92.784 (5)
K1—O32.810 (3)K1—Cl1'3.197 (14)
K1—O42.744 (4)C1—O11.385 (5)
K1—O52.791 (4)C20—O11.388 (5)
K1—O62.975 (4)
C1—O1—C20118.6 (4)C10—O4—C11116.9 (5)
C6—O2—C7116.5 (4)C13—O5—C12114.7 (5)
C9—O3—C8113.0 (4)C15—O6—C14116.9 (4)
C7—O2—C6—C1174.6 (4)
 

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