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The structure of the title compound, C42H32O6, is an important example of the functionalization of the upper rim of calix[4]arene mol­ecules. It possesses crystallographic twofold rotation symmetry and displays the calixarene cone conformation. The hydr­oxyl groups form intra­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046691/at2150sup1.cif
Contains datablocks 2, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046691/at21502sup2.hkl
Contains datablock 2

CCDC reference: 629408

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.065
  • wR factor = 0.174
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT416_ALERT_2_C Short Intra D-H..H-D H1 .. H2 .. 1.97 Ang. PLAT731_ALERT_1_C Bond Calc 0.87(5), Rep 0.863(19) ...... 2.63 su-Ra O1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.87(5), Rep 0.863(19) ...... 2.63 su-Ra O1 -H1 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.80(5), Rep 1.81(2) ...... 2.50 su-Ra H1 -O2 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 6 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

5,17-Dibenzoyl-25,26,27,28-tetrahydroxycalix[4]arene top
Crystal data top
C42H32O6F(000) = 1328
Mr = 632.68Dx = 1.319 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 896 reflections
a = 18.615 (4) Åθ = 2.4–19.4°
b = 15.609 (4) ŵ = 0.09 mm1
c = 12.220 (3) ÅT = 293 K
β = 116.187 (4)°Pillar, colourless
V = 3186.1 (13) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2819 independent reflections
Radiation source: fine-focus sealed tube1253 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 2221
Tmin = 0.983, Tmax = 0.991k = 918
6625 measured reflectionsl = 1414
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.0737P)2]
where P = (Fo2 + 2Fc2)/3
2819 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.18 e Å3
2 restraintsΔρmin = 0.18 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*/Ueq
O10.61452 (15)0.21936 (16)0.3326 (3)0.0742 (8)
O20.49643 (16)0.22187 (18)0.3994 (3)0.0750 (8)
O30.7746 (2)0.5782 (2)0.3615 (3)0.1147 (11)
C10.6587 (2)0.2909 (3)0.1571 (4)0.0770 (12)
H1A0.70210.30130.13510.092*
H1B0.65380.22950.16330.092*
C20.67922 (19)0.3318 (2)0.2804 (3)0.0615 (10)
C30.72060 (19)0.4082 (2)0.3116 (3)0.0649 (10)
H3A0.73640.43340.25680.078*
C40.73931 (19)0.4484 (2)0.4211 (4)0.0614 (10)
C50.7140 (2)0.4102 (2)0.5006 (3)0.0639 (10)
H5A0.72610.43670.57490.077*
C60.67166 (19)0.3344 (2)0.4737 (3)0.0586 (9)
C70.6449 (2)0.2963 (2)0.5640 (3)0.0733 (11)
H7A0.68440.31000.64610.088*
H7B0.64290.23440.55560.088*
C80.5631 (2)0.3286 (3)0.5467 (3)0.0648 (10)
C90.5585 (3)0.3974 (3)0.6149 (4)0.0835 (13)
H9A0.60530.42210.67300.100*
C100.4856 (3)0.4296 (3)0.5976 (4)0.0954 (14)
H10A0.48320.47560.64410.114*
C110.4164 (3)0.3938 (3)0.5117 (4)0.0860 (13)
H11A0.36730.41620.50050.103*
C120.4179 (2)0.3255 (3)0.4417 (3)0.0664 (10)
C130.4923 (2)0.2930 (3)0.4626 (3)0.0629 (10)
C140.65515 (19)0.2961 (2)0.3638 (4)0.0599 (10)
C150.7816 (2)0.5317 (3)0.4477 (4)0.0774 (11)
C160.8328 (2)0.5604 (3)0.5748 (4)0.0767 (11)
C170.8709 (2)0.5027 (3)0.6703 (4)0.0882 (13)
H17A0.86380.44410.65560.106*
C180.9189 (3)0.5319 (4)0.7862 (5)0.1055 (16)
H18A0.94400.49300.84960.127*
C190.9299 (3)0.6176 (4)0.8081 (6)0.1150 (19)
H19A0.96220.63720.88660.138*
C200.8929 (3)0.6761 (4)0.7136 (6)0.1131 (18)
H20A0.90030.73460.72870.136*
C210.8458 (3)0.6471 (3)0.5991 (5)0.0901 (14)
H21A0.82190.68630.53590.108*
H10.578 (2)0.214 (4)0.358 (5)0.16 (3)*
H20.465 (2)0.217 (3)0.3275 (19)0.095 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0588 (16)0.0505 (16)0.102 (2)0.0019 (13)0.0252 (16)0.0049 (15)
O20.0639 (18)0.0621 (19)0.081 (2)0.0024 (14)0.0159 (17)0.0075 (17)
O30.149 (3)0.091 (2)0.102 (2)0.027 (2)0.053 (2)0.003 (2)
C10.059 (2)0.077 (3)0.096 (3)0.010 (2)0.036 (2)0.026 (3)
C20.043 (2)0.060 (2)0.074 (3)0.0026 (18)0.0195 (19)0.013 (2)
C30.053 (2)0.069 (3)0.071 (3)0.0035 (19)0.025 (2)0.007 (2)
C40.055 (2)0.055 (2)0.069 (2)0.0048 (18)0.022 (2)0.006 (2)
C50.056 (2)0.060 (3)0.061 (2)0.0046 (19)0.0124 (19)0.006 (2)
C60.044 (2)0.051 (2)0.064 (2)0.0042 (18)0.0086 (18)0.005 (2)
C70.066 (2)0.066 (3)0.064 (2)0.004 (2)0.007 (2)0.013 (2)
C80.067 (3)0.064 (3)0.057 (2)0.008 (2)0.021 (2)0.022 (2)
C90.087 (3)0.092 (4)0.062 (3)0.002 (3)0.025 (2)0.006 (3)
C100.112 (4)0.107 (4)0.074 (3)0.011 (3)0.048 (3)0.001 (3)
C110.086 (3)0.099 (4)0.079 (3)0.015 (3)0.041 (3)0.014 (3)
C120.063 (3)0.069 (3)0.067 (2)0.005 (2)0.028 (2)0.022 (2)
C130.065 (3)0.056 (2)0.061 (2)0.004 (2)0.021 (2)0.018 (2)
C140.041 (2)0.046 (2)0.079 (3)0.0020 (17)0.0142 (19)0.004 (2)
C150.077 (3)0.071 (3)0.084 (3)0.007 (2)0.036 (2)0.004 (3)
C160.070 (3)0.076 (3)0.086 (3)0.016 (2)0.036 (2)0.015 (3)
C170.073 (3)0.087 (3)0.092 (3)0.012 (2)0.025 (3)0.022 (3)
C180.080 (3)0.122 (5)0.099 (4)0.019 (3)0.025 (3)0.029 (3)
C190.105 (4)0.135 (5)0.108 (4)0.040 (4)0.050 (4)0.052 (4)
C200.123 (5)0.101 (4)0.134 (5)0.039 (4)0.074 (4)0.061 (4)
C210.104 (4)0.067 (3)0.115 (4)0.020 (3)0.063 (3)0.023 (3)
Geometric parameters (Å, º) top
O1—C141.378 (4)C8—C131.381 (5)
O1—H10.863 (19)C8—C91.385 (5)
O2—C131.373 (4)C9—C101.373 (6)
O2—H20.817 (19)C9—H9A0.9300
O3—C151.238 (4)C10—C111.372 (6)
C1—C12i1.505 (5)C10—H10A0.9300
C1—C21.522 (5)C11—C121.374 (5)
C1—H1A0.9700C11—H11A0.9300
C1—H1B0.9700C12—C131.388 (5)
C2—C31.378 (5)C12—C1i1.505 (5)
C2—C141.397 (5)C15—C161.488 (5)
C3—C41.376 (5)C16—C211.383 (5)
C3—H3A0.9300C16—C171.396 (5)
C4—C51.388 (5)C17—C181.376 (5)
C4—C151.479 (5)C17—H17A0.9300
C5—C61.379 (5)C18—C191.363 (6)
C5—H5A0.9300C18—H18A0.9300
C6—C141.376 (5)C19—C201.393 (7)
C6—C71.517 (5)C19—H19A0.9300
C7—C81.527 (5)C20—C211.360 (6)
C7—H7A0.9700C20—H20A0.9300
C7—H7B0.9700C21—H21A0.9300
C14—O1—H1114 (4)C11—C10—H10A120.0
C13—O2—H2120 (3)C9—C10—H10A120.0
C12i—C1—C2112.2 (3)C10—C11—C12121.4 (4)
C12i—C1—H1A109.2C10—C11—H11A119.3
C2—C1—H1A109.2C12—C11—H11A119.3
C12i—C1—H1B109.2C11—C12—C13117.5 (4)
C2—C1—H1B109.2C11—C12—C1i120.3 (4)
H1A—C1—H1B107.9C13—C12—C1i122.1 (4)
C3—C2—C14117.6 (4)O2—C13—C8118.1 (4)
C3—C2—C1120.2 (4)O2—C13—C12119.4 (4)
C14—C2—C1122.2 (3)C8—C13—C12122.5 (4)
C4—C3—C2122.3 (4)C6—C14—O1120.4 (4)
C4—C3—H3A118.8C6—C14—C2122.2 (3)
C2—C3—H3A118.8O1—C14—C2117.3 (4)
C3—C4—C5117.8 (3)O3—C15—C4118.9 (4)
C3—C4—C15119.8 (4)O3—C15—C16119.3 (4)
C5—C4—C15122.4 (4)C4—C15—C16121.8 (4)
C6—C5—C4122.5 (4)C21—C16—C17118.4 (4)
C6—C5—H5A118.8C21—C16—C15119.3 (4)
C4—C5—H5A118.8C17—C16—C15122.2 (4)
C14—C6—C5117.6 (4)C18—C17—C16120.4 (4)
C14—C6—C7122.4 (3)C18—C17—H17A119.8
C5—C6—C7120.0 (4)C16—C17—H17A119.8
C6—C7—C8113.4 (3)C19—C18—C17120.0 (5)
C6—C7—H7A108.9C19—C18—H18A120.0
C8—C7—H7A108.9C17—C18—H18A120.0
C6—C7—H7B108.9C18—C19—C20120.3 (5)
C8—C7—H7B108.9C18—C19—H19A119.8
H7A—C7—H7B107.7C20—C19—H19A119.8
C13—C8—C9117.9 (4)C21—C20—C19119.5 (5)
C13—C8—C7122.4 (4)C21—C20—H20A120.2
C9—C8—C7119.7 (4)C19—C20—H20A120.2
C10—C9—C8120.7 (4)C20—C21—C16121.3 (5)
C10—C9—H9A119.7C20—C21—H21A119.4
C8—C9—H9A119.7C16—C21—H21A119.4
C11—C10—C9120.0 (5)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O1ii0.932.583.478 (5)163
O2—H2···O1i0.82 (2)1.86 (2)2.672 (4)171 (4)
O1—H1···O20.86 (2)1.81 (2)2.662 (4)169 (6)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+3/2, y+1/2, z+1.
 

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