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The nature of the inclusions in ten clathrate complexes of Dianin's compound have been investigated by the use of electron-density difference maps. The guest species are the first eight straight-chain carboxylic acids, formic to octanoic, a branched-chain acid (dimethylacetic acid) and trifluoroacetic acid. The point-group symmetry of the clathrate cavity, \bar 3, is satisfied by partial occupation of symmetry-related sites by two included molecules in the case of formic, acetic and trifluoroacetic acids and by a single molecule in the remainder. Hydrogen-bonding requirements in the case of formic and acetic acids are satisfied by dimer formation; in the trifluoroacetic acid complex the two acid molecules form hydrogen bonds to framework O atoms at either end of the cavity. The adoption of gauche conformations in heptanoic and octanoic acid chains shortens them sufficiently that they fit the cavity with only slight distortion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102022395/bm0059sup1.cif
Contains datablocks global, DIF, DIA, DIP, DIB, DIV, DII, DIH, DIE, DIO, DIT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIFsup2.hkl
Contains datablock DIF

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIAsup3.hkl
Contains datablock DIA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIPsup4.hkl
Contains datablock DIP

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIBsup5.hkl
Contains datablock DIB

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIIsup6.hkl
Contains datablock DII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIVsup7.hkl
Contains datablock DIV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIHsup8.hkl
Contains datablock DIH

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIEsup9.hkl
Contains datablock DIE

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIOsup10.hkl
Contains datablock DIO

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DITsup11.hkl
Contains datablock DIT

CCDC references: 205197; 205198; 205199; 205200; 205201; 205202; 205203; 205204; 205205; 205206

Computing details top

For all compounds, data collection: Stoe STADI-2; cell refinement: local; data reduction: SMALL; program(s) used to solve structure: MULTAN87; program(s) used to refine structure: SHELX76; molecular graphics: SNOOPI; software used to prepare material for publication: PLATON (Spek, 1990).

(DIF) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-formic acid top
Crystal data top
3(C18H20O2)·(CH2O2)Dx = 1.202 Mg m3
Mr = 851.01Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.19 (2) Åθ = 5–25°
c = 11.02 (1) ŵ = 0.08 mm1
V = 7056 (10) Å3T = 293 K
Z = 6Acicular, hexagonal prism, colourless
F(000) = 27360.6 × 0.2 × 0.2 mm
Data collection top
Stoe STADI-2 two-circle
diffractometer
Rint = 0.080
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ' fixed, where the angle θ' is the projection of θ on the equatorial planek = 2626
4175 measured reflectionsl = 011
1572 independent reflectionsStandard reflections: one per layer; every 20 reflections
1285 reflections with refl_observed_if_F__ > _6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.052See text
wR(F2) = 0.082 w = 1/[σ2 (F) + 0.00018F2]
S = 1.15(Δ/σ)max = 0.01
1285 reflectionsΔρmax = 0.27 e Å3
215 parametersΔρmin = 0.15 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.11790 (10)0.0542 (2)0.0210 (2)0.0662 (11)
O20.26080 (10)0.1740 (2)0.6258 (2)0.0540 (10)
C10.1600 (2)0.0723 (4)0.1105 (3)0.0467 (16)
C20.1743 (2)0.0347 (4)0.1642 (3)0.0498 (16)
C30.2152 (2)0.0538 (4)0.2555 (3)0.0481 (15)
C40.2436 (2)0.1107 (4)0.2959 (3)0.0398 (15)
C50.2292 (2)0.1475 (4)0.2377 (3)0.0449 (15)
C60.1879 (2)0.1289 (4)0.1458 (3)0.0478 (16)
C70.2871 (2)0.1296 (3)0.4010 (3)0.0391 (11)
C80.2599 (2)0.0952 (4)0.5194 (3)0.0434 (13)
C90.2249 (2)0.1139 (4)0.5936 (3)0.0438 (16)
C100.2978 (2)0.2104 (4)0.5386 (3)0.0421 (12)
C110.3122 (2)0.1925 (3)0.4314 (3)0.0398 (12)
C120.3525 (2)0.2349 (4)0.3549 (3)0.0493 (16)
C130.3768 (2)0.2925 (4)0.3816 (4)0.0551 (17)
C140.3614 (2)0.3092 (4)0.4884 (4)0.0549 (17)
C150.3222 (2)0.2680 (4)0.5669 (3)0.0520 (17)
C160.1721 (2)0.1077 (4)0.5291 (3)0.0564 (16)
C170.2087 (2)0.0831 (4)0.7150 (3)0.0606 (16)
C180.3351 (2)0.1176 (4)0.3645 (3)0.0539 (16)
C190.000000.000000.299000.3062*
O30.042700.029200.383400.2162*0.333
O40.049200.024600.321400.4698*0.333
H10.098 (3)0.014 (7)0.022 (7)0.20 (4)*
H20.1536 (2)0.0091 (4)0.1354 (3)0.080 (13)*
H30.2256 (2)0.0240 (4)0.2966 (3)0.062 (11)*
H40.2503 (2)0.1916 (4)0.2647 (3)0.077 (12)*
H50.1784 (2)0.1587 (4)0.1022 (3)0.061 (11)*
H60.2328 (2)0.0512 (4)0.4944 (3)0.053 (10)*
H70.2938 (2)0.0989 (4)0.5767 (3)0.040 (9)*
H80.3652 (2)0.2225 (4)0.2729 (3)0.054 (10)*
H90.4069 (2)0.3241 (4)0.3201 (4)0.067 (11)*
H100.3799 (2)0.3536 (4)0.5104 (4)0.068 (11)*
H110.3106 (2)0.2808 (4)0.6499 (3)0.069 (11)*
H120.1445 (2)0.0638 (4)0.5040 (3)0.097 (15)*
H130.1498 (2)0.1211 (4)0.5894 (3)0.097 (14)*
H140.1849 (2)0.1338 (4)0.4486 (3)0.099 (15)*
H150.1818 (2)0.0380 (4)0.7001 (3)0.081 (14)*
H160.2467 (2)0.0908 (4)0.7622 (3)0.098 (16)*
H170.1862 (2)0.0986 (4)0.7689 (3)0.082 (13)*
H180.3552 (2)0.1406 (4)0.2825 (3)0.070 (11)*
H190.3662 (2)0.1311 (4)0.4363 (3)0.062 (11)*
H200.3173 (2)0.0726 (4)0.3489 (3)0.098 (15)*
H210.015000.002500.206000.0071*0.333
H220.031100.029200.477100.0658*0.333
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.063 (2)0.064 (2)0.0652 (16)0.027 (2)0.0198 (15)0.0125 (16)
O20.0545 (19)0.0410 (19)0.0610 (14)0.0197 (16)0.0082 (13)0.0057 (14)
C10.043 (3)0.043 (3)0.048 (2)0.017 (2)0.002 (2)0.002 (2)
C20.058 (3)0.037 (3)0.052 (2)0.022 (3)0.004 (2)0.004 (2)
C30.056 (3)0.041 (3)0.0484 (19)0.025 (2)0.002 (2)0.003 (2)
C40.043 (3)0.032 (3)0.0434 (18)0.018 (2)0.0055 (19)0.0001 (18)
C50.047 (3)0.035 (3)0.0493 (19)0.018 (2)0.000 (2)0.001 (2)
C60.054 (3)0.042 (3)0.050 (2)0.026 (2)0.003 (2)0.002 (2)
C70.039 (2)0.034 (2)0.0479 (18)0.021 (2)0.0031 (18)0.0010 (18)
C80.045 (2)0.041 (3)0.0476 (18)0.024 (2)0.0012 (19)0.0006 (19)
C90.043 (3)0.034 (3)0.054 (2)0.019 (2)0.0005 (19)0.002 (2)
C100.035 (2)0.033 (2)0.057 (2)0.016 (2)0.002 (2)0.003 (2)
C110.036 (2)0.036 (2)0.050 (2)0.020 (2)0.0026 (19)0.0017 (19)
C120.043 (3)0.043 (3)0.056 (2)0.017 (2)0.001 (2)0.002 (2)
C130.051 (3)0.034 (3)0.068 (3)0.012 (3)0.008 (2)0.005 (2)
C140.050 (3)0.034 (3)0.078 (3)0.019 (3)0.016 (2)0.007 (2)
C150.048 (3)0.040 (3)0.072 (3)0.025 (2)0.007 (2)0.009 (2)
C160.048 (3)0.063 (3)0.064 (2)0.032 (2)0.002 (2)0.003 (2)
C170.069 (3)0.062 (3)0.055 (2)0.036 (3)0.012 (2)0.013 (2)
C180.048 (3)0.054 (3)0.067 (2)0.031 (2)0.005 (2)0.001 (2)
Geometric parameters (Å, º) top
O1—C11.401 (6)C7—C111.528 (7)
O2—C91.468 (8)C7—C181.548 (9)
O2—C101.385 (6)C8—C91.522 (9)
C1—C21.394 (9)C9—C161.534 (9)
C1—C61.388 (10)C9—C171.522 (6)
C2—C31.393 (8)C10—C111.406 (6)
C3—C41.412 (10)C10—C151.397 (10)
C4—C71.548 (7)C11—C121.406 (8)
C4—C51.399 (9)C12—C131.393 (10)
C5—C61.405 (8)C13—C141.399 (8)
C7—C81.560 (6)C14—C151.395 (9)
O1···O1i2.817 (6)O1···O1ii2.817 (6)
C9—O2—C10118.0 (3)C7—C8—C9115.9 (5)
O1—C1—C2121.3 (6)O2—C9—C8108.8 (5)
O1—C1—C6119.0 (5)C16—C9—C17110.5 (5)
C2—C1—C6119.7 (5)O2—C9—C17104.4 (4)
C1—C2—C3119.8 (6)C8—C9—C16114.9 (4)
C2—C3—C4122.2 (6)C8—C9—C17110.2 (5)
C3—C4—C5116.3 (5)O2—C9—C16107.4 (5)
C5—C4—C7123.1 (6)O2—C10—C11124.3 (6)
C3—C4—C7120.5 (5)O2—C10—C15114.5 (4)
C4—C5—C6122.1 (6)C11—C10—C15121.2 (5)
C1—C6—C5119.8 (6)C7—C11—C10121.7 (4)
C4—C7—C18108.7 (4)C10—C11—C12117.2 (5)
C11—C7—C18109.9 (5)C7—C11—C12121.0 (4)
C4—C7—C11112.0 (4)C11—C12—C13122.2 (4)
C8—C7—C18106.7 (4)C12—C13—C14119.5 (6)
C4—C7—C8111.9 (5)C13—C14—C15119.6 (6)
C8—C7—C11107.5 (4)C10—C15—C14120.4 (5)
C10—O2—C9—C840.3 (6)C4—C7—C11—C10108.3 (5)
C10—O2—C9—C1684.7 (5)C4—C7—C11—C1274.2 (7)
C10—O2—C9—C17158.0 (5)C8—C7—C11—C1015.0 (7)
C9—O2—C10—C1114.0 (8)C8—C7—C11—C12162.6 (5)
C9—O2—C10—C15168.1 (5)C18—C7—C11—C10130.8 (5)
O1—C1—C2—C3178.1 (5)C11—C7—C8—C943.8 (7)
C2—C1—C6—C51.8 (8)C18—C7—C8—C9161.7 (5)
C6—C1—C2—C32.0 (8)C18—C7—C11—C1246.8 (6)
O1—C1—C6—C5178.3 (5)C7—C8—C9—C17171.3 (5)
C1—C2—C3—C40.6 (8)C7—C8—C9—C1663.1 (7)
C2—C3—C4—C51.1 (8)C7—C8—C9—O257.4 (5)
C2—C3—C4—C7177.6 (5)O2—C10—C11—C70.5 (9)
C3—C4—C5—C61.3 (8)C15—C10—C11—C120.7 (9)
C3—C4—C7—C11179.2 (5)O2—C10—C11—C12177.1 (5)
C3—C4—C7—C1859.1 (6)C15—C10—C11—C7178.3 (5)
C5—C4—C7—C8120.2 (6)C11—C10—C15—C140.4 (9)
C5—C4—C7—C110.6 (7)O2—C10—C15—C14178.3 (5)
C5—C4—C7—C18122.3 (6)C10—C11—C12—C131.2 (9)
C3—C4—C7—C858.5 (7)C7—C11—C12—C13178.8 (5)
C7—C4—C5—C6177.4 (5)C11—C12—C13—C140.7 (9)
C4—C5—C6—C10.1 (8)C12—C13—C14—C150.3 (9)
C4—C7—C8—C979.5 (6)C13—C14—C15—C100.9 (9)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
(DIA) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-acetic acid top
Crystal data top
3(C18H20O2)·(C2H4O2)Dx = 1.216 Mg m3
Mr = 865.14Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.19 (2) Åθ = 5–22.5°
c = 11.06 (1) ŵ = 0.08 mm1
V = 7081 (10) Å3T = 293 K
Z = 6Acicular, hexagonal prism, colourless
F(000) = 27780.5 × 0.15 × 0.15 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.047
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ' fixed, where the angle θ'is the projection of θ on the equatorial planek = 2626
4483 measured reflectionsl = 011
1535 independent reflectionsStandard reflections: one per layer; every 20 reflections
1165 reflections with refl_obs_if_F_ > _6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.064See text
wR(F2) = 0.082 w = 1/[σ2(F) + 0.0002F2]
S = 1.45(Δ/σ)max = 0.002
1165 reflectionsΔρmax = 0.42 e Å3
215 parametersΔρmin = 0.38 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. Only values for the host (DIN) are listed. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1221 (2)0.0565 (4)0.0173 (4)0.0641 (19)
O20.2613 (2)0.1741 (4)0.6248 (3)0.0540 (16)
C10.1627 (2)0.0732 (5)0.1092 (4)0.045 (2)
C20.1757 (2)0.0355 (5)0.1636 (5)0.050 (2)
C30.2157 (2)0.0540 (4)0.2562 (4)0.048 (2)
C40.2438 (2)0.1106 (4)0.2973 (4)0.040 (2)
C50.2296 (2)0.1477 (4)0.2377 (4)0.044 (2)
C60.1894 (2)0.1293 (4)0.1445 (4)0.045 (2)
C70.2872 (2)0.1292 (4)0.4018 (4)0.038 (2)
C80.2594 (2)0.0944 (4)0.5181 (4)0.043 (2)
C90.2245 (2)0.1140 (4)0.5919 (4)0.043 (2)
C100.2981 (2)0.2102 (4)0.5378 (4)0.044 (2)
C110.3124 (2)0.1925 (4)0.4316 (4)0.040 (2)
C120.3528 (2)0.2351 (4)0.3571 (4)0.048 (2)
C130.3770 (3)0.2927 (6)0.3819 (5)0.055 (2)
C140.3619 (3)0.3096 (6)0.4876 (5)0.056 (2)
C150.3227 (3)0.2684 (5)0.5657 (5)0.053 (2)
C160.1721 (2)0.1082 (4)0.5282 (5)0.056 (2)
C170.2078 (3)0.0823 (6)0.7118 (4)0.059 (3)
C180.3356 (2)0.1176 (4)0.3657 (5)0.051 (2)
O30.049100.031000.379300.1509*0.333
O40.046500.024700.359700.2485*0.333
C210.005100.007400.174600.1668*0.333
C200.000800.003500.314300.2054*0.667
H10.109 (3)0.023 (7)0.008 (7)0.12 (4)*
H20.1550 (2)0.0083 (5)0.1350 (5)0.062 (16)*
H30.2258 (2)0.0242 (4)0.2978 (4)0.046 (14)*
H40.2504 (2)0.1916 (4)0.2655 (4)0.085 (19)*
H50.1799 (2)0.1591 (4)0.1009 (4)0.046 (14)*
H60.2318 (2)0.0506 (4)0.4926 (4)0.070 (17)*
H70.2930 (2)0.0975 (4)0.5755 (4)0.054 (15)*
H80.3657 (2)0.2226 (4)0.2758 (4)0.053 (14)*
H90.4072 (3)0.3242 (6)0.3204 (5)0.053 (14)*
H100.3802 (3)0.3541 (6)0.5091 (5)0.083 (19)*
H110.3114 (3)0.2812 (5)0.6488 (5)0.051 (14)*
H120.1444 (2)0.0643 (4)0.5031 (5)0.11 (2)*
H130.1498 (2)0.1216 (4)0.5884 (5)0.11 (2)*
H140.1849 (2)0.1343 (4)0.4481 (5)0.11 (2)*
H150.1805 (3)0.0375 (6)0.6953 (4)0.08 (2)*
H160.2455 (3)0.0891 (6)0.7587 (4)0.10 (2)*
H170.1856 (3)0.0979 (6)0.7664 (4)0.09 (2)*
H180.3560 (2)0.1410 (4)0.2845 (5)0.12 (2)*
H190.3664 (2)0.1310 (4)0.4379 (5)0.044 (13)*
H200.3180 (2)0.0727 (4)0.3496 (5)0.073 (18)*
H220.049100.033400.148500.4679*0.333
H230.011600.034600.137100.1907*0.333
H240.019000.026200.140900.2025*0.333
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.063 (4)0.061 (3)0.063 (3)0.027 (3)0.016 (2)0.006 (2)
O20.055 (3)0.043 (3)0.058 (2)0.020 (3)0.007 (2)0.008 (2)
C10.044 (5)0.045 (4)0.035 (3)0.015 (4)0.007 (3)0.004 (3)
C20.057 (5)0.036 (4)0.048 (3)0.017 (4)0.001 (3)0.003 (3)
C30.055 (4)0.038 (4)0.052 (3)0.025 (4)0.005 (3)0.002 (3)
C40.046 (4)0.036 (4)0.040 (3)0.022 (3)0.005 (3)0.002 (3)
C50.040 (4)0.035 (4)0.053 (3)0.015 (3)0.001 (3)0.001 (3)
C60.049 (4)0.043 (4)0.047 (3)0.025 (4)0.004 (3)0.001 (3)
C70.038 (4)0.036 (4)0.043 (3)0.021 (3)0.000 (3)0.002 (3)
C80.045 (4)0.040 (4)0.050 (3)0.026 (3)0.005 (3)0.001 (3)
C90.047 (4)0.033 (4)0.048 (3)0.020 (4)0.003 (3)0.002 (3)
C100.035 (4)0.036 (4)0.059 (3)0.017 (3)0.001 (3)0.003 (3)
C110.038 (4)0.037 (4)0.043 (3)0.018 (3)0.006 (3)0.006 (3)
C120.044 (4)0.040 (4)0.052 (3)0.015 (4)0.002 (3)0.005 (3)
C130.054 (4)0.036 (4)0.064 (4)0.015 (4)0.005 (4)0.007 (3)
C140.054 (4)0.034 (4)0.076 (4)0.019 (4)0.020 (4)0.007 (4)
C150.053 (4)0.042 (4)0.069 (4)0.028 (4)0.008 (3)0.008 (3)
C160.046 (4)0.051 (4)0.072 (4)0.026 (4)0.001 (3)0.001 (3)
C170.069 (5)0.057 (5)0.053 (3)0.033 (4)0.010 (3)0.010 (3)
C180.047 (4)0.051 (4)0.064 (3)0.031 (4)0.004 (3)0.005 (3)
Geometric parameters (Å, º) top
O1—C11.399 (9)C7—C111.537 (10)
O2—C91.473 (10)C7—C181.551 (10)
O2—C101.381 (8)C8—C91.535 (9)
C1—C21.378 (11)C9—C171.522 (8)
C1—C61.378 (11)C9—C161.525 (9)
C2—C31.392 (9)C10—C151.410 (12)
C3—C41.408 (10)C10—C111.396 (8)
C4—C51.411 (9)C11—C121.398 (9)
C4—C71.545 (8)C12—C131.389 (12)
C5—C61.400 (8)C13—C141.391 (10)
C7—C81.551 (8)C14—C151.394 (12)
O1···O1i2.903 (12)O1···O1ii2.903 (11)
C9—O2—C10117.7 (4)C7—C8—C9115.2 (5)
O1—C1—C6117.3 (7)C8—C9—C17109.1 (6)
O1—C1—C2122.0 (8)C16—C9—C17110.2 (6)
C2—C1—C6120.7 (6)O2—C9—C17104.9 (5)
C1—C2—C3119.8 (8)O2—C9—C8108.8 (5)
C2—C3—C4122.1 (6)O2—C9—C16108.1 (6)
C5—C4—C7123.6 (6)C8—C9—C16115.2 (4)
C3—C4—C5116.0 (5)O2—C10—C11124.7 (6)
C3—C4—C7120.5 (6)O2—C10—C15114.4 (5)
C4—C5—C6122.2 (6)C11—C10—C15120.9 (6)
C1—C6—C5119.3 (6)C7—C11—C12121.8 (5)
C8—C7—C18107.1 (5)C10—C11—C12116.7 (6)
C11—C7—C18109.5 (6)C7—C11—C10121.4 (5)
C8—C7—C11108.3 (4)C11—C12—C13123.4 (5)
C4—C7—C18109.1 (4)C12—C13—C14119.1 (7)
C4—C7—C8111.2 (5)C13—C14—C15119.3 (8)
C4—C7—C11111.5 (5)C10—C15—C14120.6 (6)
C10—O2—C9—C841.6 (7)C4—C7—C11—C10108.5 (6)
C10—O2—C9—C1684.2 (7)C4—C7—C11—C1274.7 (8)
C10—O2—C9—C17158.2 (7)C8—C7—C11—C1014.1 (8)
C9—O2—C10—C1115.1 (10)C8—C7—C11—C12162.6 (6)
C9—O2—C10—C15166.8 (6)C18—C7—C11—C10130.6 (6)
O1—C1—C2—C3178.8 (6)C11—C7—C8—C942.8 (7)
C2—C1—C6—C50.8 (9)C18—C7—C8—C9160.9 (5)
C6—C1—C2—C30.8 (10)C18—C7—C11—C1246.2 (7)
O1—C1—C6—C5178.8 (6)C7—C8—C9—C17171.3 (6)
C1—C2—C3—C40.1 (10)C7—C8—C9—C1664.2 (8)
C2—C3—C4—C50.9 (9)C7—C8—C9—O257.3 (6)
C2—C3—C4—C7179.0 (6)O2—C10—C11—C70.3 (10)
C3—C4—C5—C60.9 (9)C15—C10—C11—C121.4 (10)
C3—C4—C7—C11179.9 (5)O2—C10—C11—C12176.6 (6)
C3—C4—C7—C1859.0 (7)C15—C10—C11—C7178.3 (7)
C5—C4—C7—C8121.0 (6)C11—C10—C15—C140.0 (12)
C5—C4—C7—C110.0 (8)O2—C10—C15—C14178.2 (8)
C5—C4—C7—C18121.2 (6)C10—C11—C12—C132.3 (10)
C3—C4—C7—C858.9 (7)C7—C11—C12—C13179.2 (7)
C7—C4—C5—C6179.0 (5)C11—C12—C13—C141.8 (12)
C4—C5—C6—C10.1 (9)C12—C13—C14—C150.3 (13)
C4—C7—C8—C980.0 (7)C13—C14—C15—C100.6 (13)
Symmetry codes: (i) xy, x, z; (ii) y, x+y, z.
(DIP) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-propionic acid top
Crystal data top
6(C18H20O2)·(C3H6O2)Dx = 1.187 Mg m3
Mr = 1683.1Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.24 (2) Åθ = 5–22.5°
c = 10.96 (1) ŵ = 0.08 mm1
V = 7043 (10) Å3T = 293 K
Z = 3Acicular, hexagonal prism, colourless
F(000) = 27120.5 × 0.15 × 0.15 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.056
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ' fixed, where the angle θ' is the projection of θ on the equatorial plane.k = 2626
4108 measured reflectionsl = 011
1555 independent reflectionsStandard reflections: one per layer; every 20 reflections
1211 reflections with refl_observed_if_F_ > _6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.061See text
wR(F2) = 0.092 w = 1/[σ2(F) + 0.00015F2]
S = 1.23(Δ/σ)max = 0.001
1211 reflectionsΔρmax = 0.33 e Å3
215 parametersΔρmin = 0.19 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1194 (2)0.0557 (4)0.0183 (3)0.0607 (16)
O20.26100 (10)0.1745 (2)0.6256 (3)0.0516 (11)
C10.1610 (2)0.0732 (4)0.1092 (4)0.0432 (19)
C20.1747 (2)0.0356 (4)0.1639 (4)0.045 (2)
C30.2153 (2)0.0542 (4)0.2561 (4)0.0430 (19)
C40.2432 (2)0.1109 (4)0.2958 (3)0.0360 (16)
C50.2293 (2)0.1478 (4)0.2364 (4)0.041 (2)
C60.1884 (2)0.1296 (4)0.1444 (4)0.0432 (19)
C70.2869 (2)0.1294 (4)0.4008 (3)0.0362 (16)
C80.2599 (2)0.0952 (4)0.5191 (3)0.0386 (16)
C90.2247 (2)0.1140 (4)0.5935 (4)0.0417 (17)
C100.2982 (2)0.2108 (4)0.5380 (4)0.0408 (17)
C110.3125 (2)0.1927 (4)0.4313 (4)0.0384 (16)
C120.3527 (2)0.2349 (4)0.3551 (4)0.047 (2)
C130.3767 (2)0.2924 (4)0.3816 (4)0.052 (2)
C140.3612 (2)0.3090 (4)0.4875 (5)0.052 (2)
C150.3224 (2)0.2685 (4)0.5666 (4)0.0492 (19)
C160.1721 (2)0.1078 (4)0.5292 (4)0.054 (2)
C170.2092 (2)0.0832 (4)0.7162 (4)0.056 (2)
C180.3350 (2)0.1175 (4)0.3637 (4)0.0494 (19)
O30.009700.000000.167600.2249*0.167
O40.061000.051200.294300.2774*0.167
C200.008100.019000.274800.2012*0.167
C210.028900.011800.386100.2510*0.167
C220.007700.009500.501800.1605*0.167
H10.105 (4)0.019 (8)0.011 (7)0.17 (4)*
H20.1538 (2)0.0081 (4)0.1349 (4)0.044 (12)*
H30.2255 (2)0.0245 (4)0.2978 (4)0.075 (16)*
H40.2509 (2)0.1919 (4)0.2627 (4)0.062 (14)*
H50.1783 (2)0.1591 (4)0.1012 (4)0.070 (15)*
H60.2326 (2)0.0514 (4)0.4938 (3)0.058 (14)*
H70.2936 (2)0.0986 (4)0.5767 (3)0.041 (12)*
H80.3655 (2)0.2225 (4)0.2729 (4)0.069 (14)*
H90.4072 (2)0.3239 (4)0.3201 (4)0.067 (14)*
H100.3793 (2)0.3534 (4)0.5084 (5)0.072 (15)*
H110.3108 (2)0.2813 (4)0.6499 (4)0.059 (13)*
H120.1446 (2)0.0640 (4)0.5044 (4)0.092 (19)*
H130.1498 (2)0.1212 (4)0.5898 (4)0.082 (16)*
H140.1847 (2)0.1337 (4)0.4480 (4)0.13 (2)*
H150.1824 (2)0.0382 (4)0.7011 (4)0.082 (18)*
H160.2473 (2)0.0909 (4)0.7627 (4)0.11 (2)*
H170.1868 (2)0.0985 (4)0.7713 (4)0.090 (18)*
H180.3552 (2)0.1406 (4)0.2814 (4)0.067 (15)*
H190.3660 (2)0.1310 (4)0.4362 (4)0.070 (15)*
H200.3173 (2)0.0726 (4)0.3478 (4)0.068 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.060 (3)0.061 (3)0.058 (2)0.028 (3)0.018 (2)0.011 (2)
O20.053 (2)0.042 (2)0.0560 (18)0.021 (2)0.0064 (17)0.0096 (18)
C10.039 (4)0.044 (3)0.039 (3)0.015 (3)0.004 (3)0.005 (3)
C20.055 (4)0.030 (4)0.045 (3)0.017 (3)0.003 (3)0.004 (3)
C30.047 (3)0.037 (4)0.045 (3)0.021 (3)0.004 (3)0.004 (3)
C40.039 (3)0.032 (3)0.036 (2)0.017 (3)0.006 (2)0.000 (2)
C50.047 (4)0.029 (4)0.042 (2)0.016 (3)0.001 (3)0.000 (3)
C60.049 (3)0.039 (4)0.047 (3)0.026 (3)0.006 (3)0.004 (3)
C70.038 (3)0.034 (3)0.042 (2)0.022 (3)0.002 (2)0.002 (2)
C80.043 (3)0.038 (3)0.041 (2)0.025 (3)0.002 (2)0.002 (2)
C90.044 (3)0.034 (3)0.045 (3)0.018 (3)0.005 (3)0.001 (3)
C100.033 (3)0.038 (3)0.049 (3)0.016 (3)0.000 (3)0.005 (3)
C110.036 (3)0.038 (3)0.042 (2)0.019 (3)0.006 (2)0.005 (3)
C120.046 (4)0.040 (4)0.050 (3)0.017 (3)0.001 (3)0.005 (3)
C130.052 (4)0.038 (4)0.055 (3)0.015 (3)0.005 (3)0.005 (3)
C140.044 (4)0.035 (4)0.072 (3)0.016 (3)0.017 (3)0.004 (3)
C150.048 (3)0.034 (4)0.065 (3)0.020 (3)0.010 (3)0.013 (3)
C160.041 (4)0.063 (4)0.066 (3)0.031 (3)0.001 (3)0.011 (3)
C170.065 (4)0.061 (4)0.048 (3)0.035 (4)0.013 (3)0.010 (3)
C180.049 (3)0.048 (4)0.063 (3)0.033 (3)0.002 (3)0.001 (3)
Geometric parameters (Å, º) top
O1—C11.401 (8)C7—C111.539 (10)
O2—C91.479 (8)C7—C181.553 (10)
O2—C101.387 (7)C8—C91.529 (9)
C1—C21.389 (9)C9—C171.529 (7)
C1—C61.385 (10)C9—C161.528 (9)
C2—C31.393 (8)C10—C151.403 (10)
C3—C41.407 (10)C10—C111.398 (8)
C4—C51.399 (9)C11—C121.400 (9)
C4—C71.548 (7)C12—C131.393 (10)
C5—C61.397 (8)C13—C141.386 (8)
C7—C81.551 (7)C14—C151.386 (9)
O1···O1i2.847 (11)O1···O1ii2.847 (12)
C9—O2—C10118.2 (4)C7—C8—C9115.7 (5)
O1—C1—C6118.1 (6)C16—C9—C17111.0 (5)
C2—C1—C6120.2 (5)O2—C9—C16107.5 (5)
O1—C1—C2121.7 (6)O2—C9—C17104.5 (4)
C1—C2—C3120.1 (6)C8—C9—C17109.4 (5)
C2—C3—C4121.2 (6)O2—C9—C8108.6 (5)
C5—C4—C7123.5 (6)C8—C9—C16115.3 (4)
C3—C4—C7119.5 (6)O2—C10—C11124.1 (6)
C3—C4—C5116.9 (5)C11—C10—C15121.6 (6)
C4—C5—C6122.4 (6)O2—C10—C15114.2 (4)
C1—C6—C5119.1 (6)C7—C11—C10121.8 (5)
C8—C7—C18106.8 (5)C10—C11—C12116.8 (6)
C11—C7—C18109.5 (6)C7—C11—C12121.4 (5)
C8—C7—C11107.7 (4)C11—C12—C13122.2 (5)
C4—C7—C8111.7 (5)C12—C13—C14119.5 (6)
C4—C7—C11111.7 (5)C13—C14—C15120.0 (6)
C4—C7—C18109.2 (4)C10—C15—C14119.8 (5)
C10—O2—C9—C840.2 (6)C4—C7—C11—C10107.5 (6)
C10—O2—C9—C1685.1 (5)C4—C7—C11—C1274.6 (7)
C10—O2—C9—C17156.9 (5)C8—C7—C11—C1015.5 (8)
C9—O2—C10—C1114.0 (8)C8—C7—C11—C12162.4 (6)
C9—O2—C10—C15167.8 (5)C18—C7—C11—C10131.4 (6)
O1—C1—C2—C3178.4 (5)C11—C7—C8—C944.3 (7)
C2—C1—C6—C50.8 (9)C18—C7—C8—C9161.9 (5)
C6—C1—C2—C31.2 (9)C18—C7—C11—C1246.5 (7)
O1—C1—C6—C5178.9 (5)C7—C8—C9—C17170.8 (5)
C1—C2—C3—C40.0 (9)C7—C8—C9—C1663.2 (8)
C2—C3—C4—C51.6 (8)C7—C8—C9—O257.4 (6)
C2—C3—C4—C7178.4 (5)O2—C10—C11—C70.8 (10)
C3—C4—C5—C62.0 (8)C15—C10—C11—C120.8 (9)
C3—C4—C7—C11179.7 (5)O2—C10—C11—C12177.2 (5)
C3—C4—C7—C1859.0 (7)C15—C10—C11—C7178.8 (6)
C5—C4—C7—C8121.0 (6)C11—C10—C15—C140.5 (10)
C5—C4—C7—C110.3 (7)O2—C10—C15—C14178.6 (5)
C5—C4—C7—C18121.0 (6)C10—C11—C12—C131.5 (9)
C3—C4—C7—C859.0 (7)C7—C11—C12—C13179.5 (6)
C7—C4—C5—C6178.0 (5)C11—C12—C13—C140.9 (10)
C4—C5—C6—C10.9 (9)C12—C13—C14—C150.5 (10)
C4—C7—C8—C978.7 (7)C13—C14—C15—C101.1 (10)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.88 (12)1.99 (12)2.847 (11)166 (12)
Symmetry code: (i) y, x+y, z.
(DIB) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-butyric acid top
Crystal data top
6(C18H20O2)·(C4H8O2)Dx = 1.189 Mg m3
Mr = 1698.3Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.26 (2) Åθ = 5–25°
c = 11.00 (1) ŵ = 0.08 mm1
V = 7079 (10) Å3T = 293 K
Z = 3Acicular, hexagonal prism, colourless
F(000) = 27360.6 × 0.20 × 0.20 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.018
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ'fixed, where the angle θ' is the projection of θ on the equatorial planek = 2626
4683 measured reflectionsl = 011
1659 independent reflectionsStandard reflections: one per layer; every 20 reflections
1376 reflections with refl_obs_if_F_ > _6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.053See text
wR(F2) = 0.052 w = 1/[σ2(F) + 0.000097)
S = 1.08(Δ/σ)max = 0.001
1376 reflectionsΔρmax = 0.27 e Å3
215 parametersΔρmin = 0.15 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.11800 (10)0.0558 (2)0.0206 (2)0.0606 (11)
O20.26160 (10)0.1749 (2)0.6271 (2)0.0527 (10)
C10.1601 (2)0.0734 (4)0.1102 (3)0.0429 (15)
C20.1741 (2)0.0361 (4)0.1644 (3)0.0481 (15)
C30.2148 (2)0.0546 (4)0.2558 (3)0.0443 (15)
C40.24340 (10)0.1113 (2)0.2953 (3)0.0381 (11)
C50.22910 (10)0.1481 (3)0.2366 (3)0.0429 (15)
C60.1879 (2)0.1296 (4)0.1446 (3)0.0446 (15)
C70.28720 (10)0.1300 (2)0.4010 (3)0.0365 (11)
C80.26050 (10)0.0962 (2)0.5195 (3)0.0401 (11)
C90.2258 (2)0.1150 (4)0.5950 (3)0.0442 (11)
C100.29810 (10)0.2107 (2)0.5388 (3)0.0418 (11)
C110.31270 (10)0.1930 (2)0.4309 (3)0.0391 (11)
C120.3526 (2)0.2351 (4)0.3542 (3)0.0478 (15)
C130.3767 (2)0.2925 (4)0.3805 (3)0.0534 (16)
C140.3613 (2)0.3089 (4)0.4873 (3)0.0554 (17)
C150.3224 (2)0.2683 (4)0.5667 (3)0.0513 (16)
C160.1732 (2)0.1085 (4)0.5300 (3)0.0553 (16)
C170.2098 (2)0.0840 (4)0.7179 (3)0.0590 (16)
C180.3349 (2)0.1180 (4)0.3628 (3)0.0512 (16)
O30.008000.020200.210800.2575*0.167
O40.050100.059800.315800.3214*0.167
C200.011900.007700.307400.1864*0.167
C210.021400.023600.422200.0936*0.167
C220.005200.015100.533800.1029*0.167
C230.026700.017500.649000.1398*0.167
H10.103 (2)0.021 (5)0.015 (5)0.14 (3)*
H20.1532 (2)0.0077 (4)0.1356 (3)0.065 (11)*
H30.2248 (2)0.0248 (4)0.2974 (3)0.058 (10)*
H40.25040 (10)0.1920 (3)0.2630 (3)0.065 (11)*
H50.1781 (2)0.1592 (4)0.1011 (3)0.063 (11)*
H60.23300 (10)0.0524 (2)0.4946 (3)0.055 (10)*
H70.29440 (10)0.0996 (2)0.5761 (3)0.051 (9)*
H80.3651 (2)0.2227 (4)0.2719 (3)0.055 (9)*
H90.4070 (2)0.3240 (4)0.3190 (3)0.061 (10)*
H100.3796 (2)0.3533 (4)0.5085 (3)0.063 (10)*
H110.3110 (2)0.2813 (4)0.6497 (3)0.053 (9)*
H120.1460 (2)0.0648 (4)0.5052 (3)0.114 (17)*
H130.1507 (2)0.1219 (4)0.5899 (3)0.087 (13)*
H140.1860 (2)0.1345 (4)0.4491 (3)0.114 (16)*
H150.1831 (2)0.0391 (4)0.7027 (3)0.101 (16)*
H160.2478 (2)0.0918 (4)0.7650 (3)0.085 (14)*
H170.1872 (2)0.0992 (4)0.7723 (3)0.089 (13)*
H180.3546 (2)0.1409 (4)0.2804 (3)0.059 (10)*
H190.3662 (2)0.1316 (4)0.4342 (3)0.066 (11)*
H200.3171 (2)0.0732 (4)0.3472 (3)0.084 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.054 (2)0.056 (2)0.0658 (16)0.0230 (18)0.0184 (15)0.0104 (15)
O20.0498 (18)0.0403 (18)0.0638 (14)0.0193 (16)0.0073 (13)0.0078 (13)
C10.039 (3)0.040 (3)0.0460 (18)0.017 (2)0.0035 (19)0.0022 (19)
C20.054 (3)0.033 (3)0.0522 (19)0.018 (2)0.002 (2)0.004 (2)
C30.052 (3)0.034 (3)0.0477 (18)0.022 (2)0.0034 (18)0.0011 (19)
C40.040 (2)0.031 (2)0.0450 (17)0.019 (2)0.0053 (18)0.0018 (18)
C50.044 (3)0.035 (3)0.0488 (18)0.019 (2)0.0028 (19)0.0029 (19)
C60.047 (3)0.038 (3)0.0512 (19)0.023 (2)0.0008 (19)0.0013 (19)
C70.030 (2)0.033 (2)0.0487 (17)0.0173 (19)0.0013 (17)0.0009 (17)
C80.039 (2)0.037 (2)0.0496 (17)0.023 (2)0.0019 (18)0.0005 (18)
C90.040 (2)0.035 (2)0.0553 (19)0.017 (2)0.0003 (19)0.0001 (19)
C100.034 (2)0.036 (2)0.0560 (19)0.018 (2)0.0023 (19)0.0031 (19)
C110.034 (2)0.037 (2)0.0465 (18)0.018 (2)0.0059 (18)0.0007 (18)
C120.040 (3)0.040 (3)0.0540 (19)0.013 (2)0.0014 (19)0.005 (2)
C130.047 (3)0.035 (3)0.067 (2)0.012 (3)0.007 (2)0.007 (2)
C140.048 (3)0.034 (3)0.081 (3)0.018 (2)0.018 (2)0.005 (2)
C150.048 (3)0.039 (3)0.070 (2)0.024 (2)0.011 (2)0.012 (2)
C160.040 (3)0.061 (3)0.070 (2)0.029 (2)0.001 (2)0.004 (2)
C170.066 (3)0.064 (3)0.053 (2)0.037 (3)0.013 (2)0.013 (2)
C180.043 (3)0.049 (3)0.067 (2)0.027 (2)0.004 (2)0.002 (2)
Geometric parameters (Å, º) top
O1—C11.403 (6)C7—C111.532 (5)
O2—C91.466 (8)C7—C181.549 (8)
O2—C101.384 (5)C8—C91.527 (7)
C1—C61.380 (10)C9—C171.537 (6)
C1—C21.387 (9)C9—C161.531 (9)
C2—C31.392 (8)C10—C111.411 (5)
C3—C41.407 (8)C10—C151.399 (8)
C4—C71.558 (5)C11—C121.401 (7)
C4—C51.402 (5)C12—C131.391 (10)
C5—C61.405 (7)C13—C141.394 (7)
C7—C81.552 (5)C14—C151.392 (8)
O1···O1i2.824 (6)O1···O1ii2.824 (6)
C9—O2—C10117.4 (3)C7—C8—C9116.3 (3)
C2—C1—C6119.8 (5)O2—C9—C8109.0 (5)
O1—C1—C6118.3 (5)O2—C9—C17104.4 (4)
O1—C1—C2122.0 (6)C8—C9—C16114.1 (3)
C1—C2—C3120.4 (6)C8—C9—C17110.3 (5)
C2—C3—C4121.6 (6)C16—C9—C17110.8 (5)
C5—C4—C7123.4 (3)O2—C9—C16107.7 (5)
C3—C4—C7120.2 (3)C11—C10—C15120.8 (3)
C3—C4—C5116.4 (4)O2—C10—C11125.1 (3)
C4—C5—C6122.2 (5)O2—C10—C15114.0 (3)
C1—C6—C5119.5 (5)C7—C11—C10121.1 (3)
C8—C7—C18107.3 (3)C7—C11—C12121.3 (4)
C4—C7—C8112.2 (3)C10—C11—C12117.5 (4)
C4—C7—C11111.8 (3)C11—C12—C13122.2 (4)
C11—C7—C18109.7 (4)C12—C13—C14119.2 (5)
C8—C7—C11107.5 (3)C13—C14—C15120.4 (6)
C4—C7—C18108.4 (3)C10—C15—C14120.0 (4)
C10—O2—C9—C840.1 (5)C4—C7—C11—C10108.1 (3)
C10—O2—C9—C1684.2 (5)C4—C7—C11—C1273.9 (5)
C10—O2—C9—C17157.9 (4)C8—C7—C11—C1015.4 (4)
C9—O2—C10—C1114.4 (6)C8—C7—C11—C12162.6 (4)
C9—O2—C10—C15168.0 (5)C18—C7—C11—C10131.7 (3)
O1—C1—C2—C3177.9 (5)C11—C7—C8—C943.9 (4)
C2—C1—C6—C51.7 (8)C18—C7—C8—C9161.8 (4)
C6—C1—C2—C31.9 (8)C18—C7—C11—C1246.3 (5)
O1—C1—C6—C5178.2 (4)C7—C8—C9—C17171.4 (4)
C1—C2—C3—C40.7 (8)C7—C8—C9—C1663.1 (6)
C2—C3—C4—C50.7 (7)C7—C8—C9—O257.4 (4)
C2—C3—C4—C7177.9 (4)O2—C10—C11—C71.2 (5)
C3—C4—C5—C61.0 (6)C15—C10—C11—C120.6 (6)
C3—C4—C7—C11179.1 (4)O2—C10—C11—C12176.9 (4)
C3—C4—C7—C1859.9 (5)C15—C10—C11—C7178.7 (4)
C5—C4—C7—C8120.1 (4)C11—C10—C15—C140.3 (7)
C5—C4—C7—C110.7 (5)O2—C10—C15—C14178.0 (5)
C5—C4—C7—C18121.6 (4)C10—C11—C12—C131.2 (7)
C3—C4—C7—C858.3 (5)C7—C11—C12—C13179.3 (5)
C7—C4—C5—C6177.6 (4)C11—C12—C13—C140.8 (9)
C4—C5—C6—C10.2 (7)C12—C13—C14—C150.2 (9)
C4—C7—C8—C979.3 (4)C13—C14—C15—C100.7 (9)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
(DIV) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-valeric acid top
Crystal data top
6(C18H20O2)·(C5H10O2)Dx = 1.210 Mg m3
Mr = 1712.3Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.21 (2) Åθ = 5–25°
c = 10.93 (1) ŵ = 0.08 mm1
V = 7008 (10) Å3T = 293 K
Z = 3Acicular,hexagonal prism, colourless
F(000) = 27600.6 × 0.2 × 0.2 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.084
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan2θ'fixed, where the angle θ' is the peojection of θ on the equatorial plane.k = 2626
4214 measured reflectionsl = 011
1535 independent reflectionsStandard reflections: one per layer; every 20 reflections
1244 reflections with refl_obs_if_F_ > _6.0_σ(F) intensity decay: maximum 5% correted by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.070See text
wR(F2) = 0.053 w = 1/[σ2(F) + 0.000091F2]
S = 1.55(Δ/σ)max = 0.001
1244 reflectionsΔρmax = 0.40 e Å3
215 parametersΔρmin = 0.18 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1190 (2)0.0567 (4)0.0190 (3)0.0576 (15)
O20.26170 (10)0.1749 (2)0.6271 (2)0.0508 (11)
C10.1606 (2)0.0735 (4)0.1097 (3)0.0411 (16)
C20.1745 (2)0.0364 (4)0.1636 (3)0.0441 (16)
C30.2151 (2)0.0548 (4)0.2556 (3)0.0431 (16)
C40.2435 (2)0.1114 (4)0.2956 (3)0.0357 (15)
C50.2294 (2)0.1483 (4)0.2363 (3)0.0399 (16)
C60.1883 (2)0.1299 (4)0.1440 (3)0.0420 (16)
C70.2872 (2)0.1301 (4)0.4008 (3)0.0342 (16)
C80.2604 (2)0.0960 (4)0.5192 (3)0.0369 (15)
C90.2255 (2)0.1151 (4)0.5950 (3)0.0427 (16)
C100.2983 (2)0.2109 (4)0.5388 (3)0.0400 (16)
C110.3125 (2)0.1928 (4)0.4313 (3)0.0361 (16)
C120.3524 (2)0.2347 (4)0.3543 (3)0.0446 (16)
C130.3767 (2)0.2921 (4)0.3801 (4)0.0520 (17)
C140.3614 (2)0.3089 (4)0.4863 (4)0.0534 (17)
C150.3227 (2)0.2686 (4)0.5669 (4)0.0506 (17)
C160.1732 (2)0.1089 (4)0.5298 (4)0.0523 (17)
C170.2093 (2)0.0838 (4)0.7177 (4)0.058 (2)
C180.3348 (2)0.1178 (4)0.3633 (3)0.0478 (17)
O30.001400.022000.170400.1700*0.167
O40.040800.058400.274000.1827*0.167
C200.004400.005600.268500.1175*0.167
C210.023800.026200.386800.1458*0.167
C220.005100.013200.496200.1047*0.167
C230.021500.019800.614500.0906*0.167
C240.009900.017900.724300.1945*0.167
H10.106 (2)0.023 (5)0.015 (5)0.10 (3)*
H20.1533 (2)0.0075 (4)0.1351 (3)0.067 (13)*
H30.2252 (2)0.0249 (4)0.2969 (3)0.069 (13)*
H40.2508 (2)0.1924 (4)0.2630 (3)0.059 (12)*
H50.1788 (2)0.1598 (4)0.1001 (3)0.061 (13)*
H60.2329 (2)0.0521 (4)0.4940 (3)0.043 (11)*
H70.2944 (2)0.0994 (4)0.5763 (3)0.043 (11)*
H80.3648 (2)0.2220 (4)0.2717 (3)0.051 (11)*
H90.4071 (2)0.3235 (4)0.3180 (4)0.070 (13)*
H100.3798 (2)0.3535 (4)0.5073 (4)0.066 (13)*
H110.3114 (2)0.2816 (4)0.6506 (4)0.055 (12)*
H120.1456 (2)0.0650 (4)0.5051 (4)0.11 (2)*
H130.1508 (2)0.1225 (4)0.5901 (4)0.080 (15)*
H140.1860 (2)0.1348 (4)0.4483 (4)0.12 (2)*
H150.1822 (2)0.0388 (4)0.7022 (4)0.084 (16)*
H160.2472 (2)0.0910 (4)0.7649 (4)0.092 (17)*
H170.1871 (2)0.0994 (4)0.7727 (4)0.100 (17)*
H180.3548 (2)0.1408 (4)0.2806 (3)0.088 (15)*
H190.3660 (2)0.1311 (4)0.4354 (3)0.060 (12)*
H200.3167 (2)0.0729 (4)0.3473 (3)0.066 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.059 (3)0.055 (3)0.0542 (19)0.025 (2)0.0145 (18)0.0078 (18)
O20.049 (2)0.042 (2)0.0552 (16)0.0182 (19)0.0077 (15)0.0066 (16)
C10.040 (3)0.045 (3)0.034 (2)0.018 (3)0.004 (2)0.001 (2)
C20.054 (3)0.033 (3)0.043 (2)0.020 (3)0.003 (3)0.001 (3)
C30.050 (3)0.037 (3)0.044 (2)0.023 (3)0.004 (2)0.001 (2)
C40.038 (3)0.033 (3)0.0350 (19)0.017 (3)0.004 (2)0.001 (2)
C50.042 (3)0.030 (3)0.045 (2)0.016 (3)0.003 (2)0.002 (2)
C60.048 (3)0.036 (3)0.042 (2)0.021 (3)0.000 (2)0.003 (2)
C70.032 (3)0.031 (3)0.040 (2)0.016 (2)0.001 (2)0.002 (2)
C80.041 (3)0.035 (3)0.0388 (19)0.022 (3)0.004 (2)0.001 (2)
C90.041 (3)0.035 (3)0.048 (2)0.016 (3)0.000 (2)0.001 (2)
C100.035 (3)0.038 (3)0.048 (2)0.019 (3)0.001 (2)0.004 (2)
C110.034 (3)0.035 (3)0.039 (2)0.017 (2)0.005 (2)0.000 (2)
C120.042 (3)0.039 (3)0.043 (2)0.013 (3)0.005 (2)0.001 (2)
C130.051 (3)0.043 (3)0.056 (3)0.019 (3)0.008 (3)0.003 (3)
C140.048 (3)0.033 (3)0.075 (3)0.017 (3)0.018 (3)0.002 (3)
C150.050 (3)0.041 (3)0.065 (3)0.026 (3)0.011 (3)0.009 (3)
C160.041 (3)0.062 (3)0.057 (3)0.028 (3)0.000 (3)0.007 (3)
C170.067 (4)0.060 (4)0.049 (2)0.033 (3)0.014 (3)0.014 (3)
C180.044 (3)0.049 (3)0.054 (3)0.026 (3)0.002 (2)0.004 (2)
Geometric parameters (Å, º) top
O1—C11.398 (8)C7—C81.546 (7)
O2—C91.462 (8)C7—C181.546 (9)
O2—C101.381 (6)C8—C91.534 (9)
C1—C21.375 (9)C9—C161.524 (9)
C1—C61.381 (10)C9—C171.531 (7)
C2—C31.389 (8)C10—C151.399 (10)
C3—C41.404 (10)C10—C111.401 (7)
C4—C51.400 (9)C11—C121.396 (9)
C4—C71.546 (7)C12—C131.387 (10)
C5—C61.400 (8)C13—C141.386 (8)
C7—C111.524 (10)C14—C151.390 (9)
O1···O1i2.836 (11)O1···O1ii2.836 (12)
C9—O2—C10117.9 (3)C7—C8—C9115.8 (5)
O1—C1—C2122.6 (6)O2—C9—C17104.8 (4)
C2—C1—C6120.1 (5)O2—C9—C8108.7 (5)
O1—C1—C6117.3 (6)C8—C9—C17109.9 (5)
C1—C2—C3120.4 (6)C16—C9—C17110.8 (5)
C2—C3—C4121.6 (6)O2—C9—C16107.9 (5)
C3—C4—C5116.4 (5)C8—C9—C16114.3 (4)
C3—C4—C7120.2 (6)C11—C10—C15121.3 (5)
C5—C4—C7123.3 (6)O2—C10—C11124.4 (6)
C4—C5—C6122.2 (6)O2—C10—C15114.3 (4)
C1—C6—C5119.2 (6)C10—C11—C12117.2 (6)
C4—C7—C18108.7 (4)C7—C11—C12120.9 (4)
C8—C7—C11107.6 (4)C7—C11—C10121.8 (5)
C8—C7—C18106.7 (5)C11—C12—C13122.4 (5)
C11—C7—C18110.0 (6)C12—C13—C14119.3 (6)
C4—C7—C8111.8 (5)C13—C14—C15120.3 (6)
C4—C7—C11112.0 (5)C10—C15—C14119.6 (5)
C10—O2—C9—C840.6 (6)C4—C7—C11—C10107.8 (6)
C10—O2—C9—C1683.9 (5)C4—C7—C11—C1274.3 (7)
C10—O2—C9—C17158.0 (5)C8—C7—C11—C1015.4 (8)
C9—O2—C10—C1114.8 (8)C8—C7—C11—C12162.6 (6)
C9—O2—C10—C15167.5 (5)C18—C7—C11—C10131.2 (6)
O1—C1—C2—C3178.3 (5)C11—C7—C8—C943.8 (7)
C2—C1—C6—C51.7 (8)C18—C7—C8—C9161.8 (5)
C6—C1—C2—C32.1 (8)C18—C7—C11—C1246.7 (6)
O1—C1—C6—C5178.7 (5)C7—C8—C9—C17171.5 (5)
C1—C2—C3—C40.6 (8)C7—C8—C9—C1663.2 (8)
C2—C3—C4—C51.1 (8)C7—C8—C9—O257.4 (6)
C2—C3—C4—C7178.2 (5)O2—C10—C11—C71.2 (9)
C3—C4—C5—C61.5 (8)C15—C10—C11—C120.7 (9)
C3—C4—C7—C11179.2 (5)O2—C10—C11—C12176.9 (5)
C3—C4—C7—C1859.1 (7)C15—C10—C11—C7178.7 (6)
C5—C4—C7—C8120.9 (6)C11—C10—C15—C140.6 (9)
C5—C4—C7—C110.1 (7)O2—C10—C15—C14178.4 (5)
C5—C4—C7—C18121.7 (6)C10—C11—C12—C131.2 (9)
C3—C4—C7—C858.4 (7)C7—C11—C12—C13179.3 (6)
C7—C4—C5—C6177.8 (5)C11—C12—C13—C140.4 (10)
C4—C5—C6—C10.1 (8)C12—C13—C14—C150.9 (10)
C4—C7—C8—C979.5 (7)C13—C14—C15—C101.4 (9)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
(DII) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-isobutyric acid top
Crystal data top
6(C18H20O2)·(C4H8O2)Dx = 1.204 Mg m3
Mr = 1698.3Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.13 (2) Åθ = 5–25.0°
c = 10.97 (1) ŵ = 0.08 mm1
V = 6993 (10) Å3T = 293 K
Z = 3Acicular, hexagonal prism, colourless
F(000) = 27360.80 × 0.25 × 0.25 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.075
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ'fixed, where θ' is the projection of θ on the equatorial planek = 2626
4376 measured reflectionsl = 011
1594 independent reflectionsStandard reflections: one per layer; every 20 reflections
1353 reflections with refl_obs_if_F_ > _6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.066See text
wR(F2) = 0.057 w = 1/[σ2(F) + 0.001F2]
S = 1.23(Δ/σ)max = 0.002
1353 reflectionsΔρmax = 0.68 e Å3
215 parametersΔρmin = 0.28 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.11920 (10)0.0550 (3)0.0199 (3)0.0636 (13)
O20.26190 (10)0.1748 (2)0.6260 (2)0.0525 (11)
C10.1610 (2)0.0731 (4)0.1095 (3)0.0465 (16)
C20.1750 (2)0.0359 (4)0.1646 (4)0.0482 (16)
C30.2156 (2)0.0547 (4)0.2557 (4)0.0455 (16)
C40.2434 (2)0.1111 (4)0.2953 (3)0.0379 (15)
C50.2294 (2)0.1479 (4)0.2372 (3)0.0436 (16)
C60.1884 (2)0.1293 (4)0.1445 (3)0.0446 (16)
C70.2876 (2)0.1305 (4)0.4006 (3)0.0397 (16)
C80.2605 (2)0.0961 (4)0.5193 (3)0.0409 (16)
C90.2259 (2)0.1152 (4)0.5935 (3)0.0427 (16)
C100.2982 (2)0.2106 (4)0.5385 (3)0.0405 (16)
C110.3127 (2)0.1927 (4)0.4314 (3)0.0393 (16)
C120.3526 (2)0.2352 (4)0.3542 (3)0.0482 (16)
C130.3767 (2)0.2925 (4)0.3803 (4)0.0537 (17)
C140.3613 (2)0.3093 (4)0.4867 (4)0.0559 (17)
C150.3228 (2)0.2687 (4)0.5662 (4)0.0522 (17)
C160.1733 (2)0.1089 (4)0.5299 (4)0.0557 (16)
C170.2098 (2)0.0842 (4)0.7158 (4)0.060 (2)
C180.3354 (2)0.1183 (4)0.3632 (4)0.0539 (17)
O30.045700.019000.248700.2435*0.167
O40.044600.033700.304000.2586*0.167
C200.008500.013700.326100.2680*0.167
C210.014600.003600.461500.0634*0.167
C220.004100.048200.478500.2916*0.167
C230.023900.049200.538900.1376*0.167
H10.091 (4)0.013 (7)0.008 (7)0.17 (3)*
H20.1543 (2)0.0081 (4)0.1359 (4)0.054 (12)*
H30.2259 (2)0.0249 (4)0.2974 (4)0.069 (14)*
H40.2505 (2)0.1921 (4)0.2643 (3)0.070 (14)*
H50.1786 (2)0.1591 (4)0.1009 (3)0.053 (12)*
H60.2330 (2)0.0522 (4)0.4942 (3)0.046 (11)*
H70.2946 (2)0.0996 (4)0.5763 (3)0.063 (13)*
H80.3649 (2)0.2225 (4)0.2716 (3)0.058 (12)*
H90.4071 (2)0.3240 (4)0.3185 (4)0.055 (12)*
H100.3796 (2)0.3540 (4)0.5078 (4)0.063 (13)*
H110.3114 (2)0.2817 (4)0.6496 (4)0.069 (13)*
H120.1456 (2)0.0650 (4)0.5051 (4)0.099 (18)*
H130.1510 (2)0.1225 (4)0.5905 (4)0.068 (13)*
H140.1860 (2)0.1349 (4)0.4489 (4)0.090 (16)*
H150.1826 (2)0.0391 (4)0.7009 (4)0.068 (14)*
H160.2480 (2)0.0918 (4)0.7626 (4)0.070 (14)*
H170.1875 (2)0.0999 (4)0.7707 (4)0.067 (14)*
H180.3554 (2)0.1414 (4)0.2807 (4)0.087 (15)*
H190.3667 (2)0.1319 (4)0.4351 (4)0.059 (12)*
H200.3175 (2)0.0732 (4)0.3474 (4)0.079 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.058 (3)0.065 (2)0.0590 (17)0.024 (2)0.0186 (17)0.0096 (17)
O20.056 (2)0.042 (2)0.0553 (16)0.0212 (19)0.0086 (15)0.0061 (15)
C10.050 (3)0.046 (3)0.041 (2)0.022 (3)0.001 (2)0.002 (2)
C20.055 (3)0.035 (3)0.050 (2)0.019 (3)0.004 (2)0.005 (2)
C30.050 (3)0.037 (3)0.050 (2)0.022 (3)0.001 (2)0.000 (2)
C40.043 (3)0.034 (3)0.0393 (19)0.021 (2)0.007 (2)0.0028 (19)
C50.051 (3)0.034 (3)0.047 (2)0.022 (3)0.002 (2)0.001 (2)
C60.055 (3)0.039 (3)0.046 (2)0.028 (3)0.003 (2)0.001 (2)
C70.040 (3)0.038 (3)0.046 (2)0.023 (2)0.0002 (19)0.0025 (19)
C80.041 (3)0.040 (3)0.043 (2)0.021 (2)0.003 (2)0.002 (2)
C90.045 (3)0.037 (3)0.047 (2)0.021 (3)0.003 (2)0.001 (2)
C100.040 (3)0.038 (3)0.047 (2)0.022 (2)0.004 (2)0.002 (2)
C110.034 (3)0.032 (3)0.050 (2)0.015 (2)0.006 (2)0.002 (2)
C120.043 (3)0.043 (3)0.050 (2)0.015 (3)0.005 (2)0.000 (2)
C130.046 (3)0.041 (3)0.064 (3)0.014 (3)0.008 (3)0.005 (2)
C140.053 (3)0.036 (3)0.076 (3)0.020 (3)0.016 (3)0.005 (3)
C150.053 (3)0.045 (3)0.066 (3)0.030 (3)0.007 (2)0.011 (3)
C160.050 (3)0.064 (3)0.062 (2)0.035 (3)0.003 (2)0.005 (2)
C170.069 (4)0.061 (4)0.055 (2)0.035 (3)0.008 (3)0.010 (3)
C180.050 (3)0.055 (3)0.066 (3)0.033 (3)0.001 (2)0.001 (2)
Geometric parameters (Å, º) top
O1—C11.39 (5)C7—C111.51 (6)
O2—C91.45 (5)C7—C181.54 (6)
O2—C101.37 (5)C8—C91.51 (6)
C1—C21.38 (5)C9—C171.53 (6)
C1—C61.37 (5)C9—C161.52 (6)
C2—C31.38 (5)C10—C151.40 (5)
C3—C41.39 (5)C10—C111.40 (5)
C4—C51.39 (5)C11—C121.40 (5)
C4—C71.55 (6)C12—C131.38 (5)
C5—C61.40 (5)C13—C141.39 (5)
C7—C81.56 (6)C14—C151.38 (5)
O1···O1i2.83 (10)O1···O1ii2.83 (10)
C9—O2—C10117.4 (3)C7—C8—C9115.6 (5)
O1—C1—C6118.8 (5)C16—C9—C17110.4 (5)
O1—C1—C2121.6 (6)O2—C9—C17104.1 (4)
C2—C1—C6119.6 (5)O2—C9—C8109.0 (5)
C1—C2—C3120.4 (6)O2—C9—C16108.0 (5)
C2—C3—C4121.6 (6)C8—C9—C16114.9 (4)
C3—C4—C5117.0 (5)C8—C9—C17109.9 (5)
C3—C4—C7120.4 (6)O2—C10—C11124.7 (6)
C5—C4—C7122.7 (6)C11—C10—C15120.8 (5)
C4—C5—C6121.9 (6)O2—C10—C15114.4 (4)
C1—C6—C5119.6 (6)C10—C11—C12117.2 (6)
C8—C7—C18106.8 (5)C7—C11—C12121.0 (4)
C11—C7—C18110.0 (6)C7—C11—C10121.8 (5)
C4—C7—C18108.5 (4)C11—C12—C13122.4 (5)
C4—C7—C8111.5 (5)C12—C13—C14119.5 (6)
C4—C7—C11112.7 (5)C13—C14—C15120.0 (6)
C8—C7—C11107.2 (4)C10—C15—C14120.2 (5)
C10—O2—C9—C841.1 (6)C4—C7—C11—C10107.5 (6)
C10—O2—C9—C1684.4 (5)C4—C7—C11—C1273.7 (7)
C10—O2—C9—C17158.3 (5)C8—C7—C11—C1015.6 (8)
C9—O2—C10—C1115.2 (8)C8—C7—C11—C12163.2 (6)
C9—O2—C10—C15167.4 (5)C18—C7—C11—C10131.4 (6)
O1—C1—C2—C3178.2 (5)C11—C7—C8—C943.9 (7)
C2—C1—C6—C51.2 (8)C18—C7—C8—C9161.8 (5)
C6—C1—C2—C31.0 (8)C18—C7—C11—C1247.5 (7)
O1—C1—C6—C5178.1 (5)C7—C8—C9—C17171.3 (5)
C1—C2—C3—C40.3 (9)C7—C8—C9—C1663.6 (8)
C2—C3—C4—C51.4 (8)C7—C8—C9—O257.8 (6)
C2—C3—C4—C7178.2 (5)O2—C10—C11—C71.7 (9)
C3—C4—C5—C61.2 (8)C15—C10—C11—C120.1 (9)
C3—C4—C7—C11179.4 (5)O2—C10—C11—C12177.2 (5)
C3—C4—C7—C1858.6 (7)C15—C10—C11—C7179.0 (6)
C5—C4—C7—C8120.8 (6)C11—C10—C15—C140.9 (10)
C5—C4—C7—C110.2 (7)O2—C10—C15—C14178.5 (5)
C5—C4—C7—C18121.8 (6)C10—C11—C12—C130.6 (9)
C3—C4—C7—C858.8 (7)C7—C11—C12—C13179.5 (6)
C7—C4—C5—C6178.4 (5)C11—C12—C13—C140.1 (10)
C4—C5—C6—C10.0 (8)C12—C13—C14—C151.0 (9)
C4—C7—C8—C979.9 (7)C13—C14—C15—C101.5 (9)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
(DIH) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-hexanoic acid top
Crystal data top
6(C18H20O2)·(C6H12O2)Dx = 1.207 Mg m3
Mr = 1726.3Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.28 (2) Åθ = 5–25°
c = 10.98 (1) ŵ = 0.08 mm1
V = 7077 (10) Å3T = 293 K
Z = 3Acicular,hexagonal prism, colourless
F(000) = 27840.6 × 0.2 × 0.2 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.083
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ'fixed, where the angle θ' is the projection of θ on the equatorial planek = 2626
4423 measured reflectionsl = 011
1582 independent reflectionsStandard reflections: one per layer; every 20 reflections
1249 reflections with refl_obs_if_F_ > _6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.076See text
wR(F2) = 0.055 w = 1/[σ2(F) + 0.000077F2]
S = 1.14(Δ/σ)max = 0.0001
1249 reflectionsΔρmax = 0.30 e Å3
215 parametersΔρmin = 0.16 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1221 (2)0.0570 (4)0.0169 (3)0.0692 (16)
O20.26210 (10)0.1751 (2)0.6262 (2)0.0530 (11)
C10.1631 (2)0.0744 (4)0.1094 (4)0.0478 (18)
C20.1765 (2)0.0367 (4)0.1636 (4)0.052 (2)
C30.2164 (2)0.0550 (4)0.2569 (4)0.0479 (16)
C40.2445 (2)0.1116 (4)0.2964 (3)0.0402 (16)
C50.2302 (2)0.1485 (4)0.2377 (3)0.0446 (16)
C60.1898 (2)0.1300 (4)0.1452 (3)0.0476 (16)
C70.2877 (2)0.1301 (4)0.4021 (3)0.0384 (16)
C80.2606 (2)0.0959 (4)0.5196 (3)0.0433 (16)
C90.2258 (2)0.1150 (4)0.5939 (3)0.0446 (16)
C100.2989 (2)0.2112 (4)0.5385 (3)0.0436 (16)
C110.3129 (2)0.1931 (4)0.4319 (3)0.0391 (16)
C120.3527 (2)0.2352 (4)0.3554 (4)0.0477 (17)
C130.3769 (2)0.2925 (4)0.3812 (4)0.0548 (19)
C140.3616 (2)0.3092 (4)0.4876 (4)0.057 (2)
C150.3230 (2)0.2689 (4)0.5666 (4)0.0514 (17)
C160.1738 (2)0.1093 (4)0.5294 (4)0.0552 (17)
C170.2094 (2)0.0838 (4)0.7157 (4)0.062 (2)
C180.3356 (2)0.1181 (4)0.3659 (4)0.0529 (17)
O30.005800.010200.122700.1421*0.167
O40.023300.036200.240500.1745*0.167
C200.012300.003800.225500.0581*0.167
C210.013300.013500.341500.1067*0.167
C220.018400.009300.453300.0352*0.167
C230.009100.016100.569500.1171*0.167
C240.024100.014300.681000.0982*0.167
C250.004400.019400.797500.2363*0.167
H10.110 (3)0.023 (6)0.015 (7)0.17 (4)*
H20.1560 (2)0.0069 (4)0.1339 (4)0.093 (16)*
H30.2258 (2)0.0250 (4)0.2998 (4)0.069 (13)*
H40.2512 (2)0.1924 (4)0.2647 (3)0.062 (13)*
H50.1798 (2)0.1596 (4)0.1021 (3)0.060 (13)*
H60.2332 (2)0.0523 (4)0.4940 (3)0.052 (12)*
H70.2942 (2)0.0991 (4)0.5770 (3)0.041 (10)*
H80.3652 (2)0.2226 (4)0.2732 (4)0.073 (13)*
H90.4069 (2)0.3238 (4)0.3190 (4)0.068 (13)*
H100.3800 (2)0.3536 (4)0.5089 (4)0.094 (16)*
H110.3115 (2)0.2818 (4)0.6497 (4)0.080 (14)*
H120.1461 (2)0.0656 (4)0.5044 (4)0.11 (2)*
H130.1516 (2)0.1230 (4)0.5893 (4)0.074 (14)*
H140.1869 (2)0.1352 (4)0.4484 (4)0.095 (16)*
H150.1824 (2)0.0390 (4)0.7002 (4)0.077 (15)*
H160.2471 (2)0.0911 (4)0.7633 (4)0.098 (18)*
H170.1870 (2)0.0993 (4)0.7699 (4)0.106 (18)*
H180.3558 (2)0.1411 (4)0.2839 (4)0.089 (15)*
H190.3664 (2)0.1312 (4)0.4383 (4)0.065 (13)*
H200.3177 (2)0.0732 (4)0.3498 (4)0.097 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.066 (3)0.072 (3)0.061 (2)0.028 (3)0.015 (2)0.0087 (19)
O20.051 (2)0.046 (2)0.0578 (16)0.0211 (19)0.0060 (15)0.0076 (16)
C10.046 (4)0.052 (3)0.042 (2)0.022 (3)0.006 (3)0.005 (2)
C20.058 (4)0.036 (4)0.055 (3)0.018 (3)0.002 (3)0.003 (3)
C30.051 (3)0.038 (3)0.053 (2)0.021 (3)0.004 (3)0.002 (3)
C40.039 (3)0.032 (3)0.046 (2)0.015 (3)0.006 (2)0.001 (2)
C50.044 (3)0.034 (3)0.051 (2)0.016 (3)0.002 (2)0.005 (2)
C60.054 (3)0.040 (3)0.048 (2)0.023 (3)0.006 (3)0.003 (3)
C70.039 (3)0.034 (3)0.046 (2)0.021 (3)0.001 (2)0.000 (2)
C80.048 (3)0.043 (3)0.046 (2)0.028 (3)0.003 (2)0.002 (2)
C90.042 (3)0.035 (3)0.051 (2)0.015 (3)0.001 (2)0.000 (2)
C100.037 (3)0.040 (3)0.052 (2)0.018 (3)0.002 (2)0.005 (2)
C110.038 (3)0.035 (3)0.044 (2)0.018 (3)0.006 (2)0.001 (2)
C120.043 (3)0.037 (3)0.055 (3)0.014 (3)0.004 (2)0.002 (3)
C130.051 (4)0.042 (3)0.063 (3)0.017 (3)0.003 (3)0.007 (3)
C140.046 (4)0.033 (4)0.083 (3)0.014 (3)0.014 (3)0.000 (3)
C150.049 (3)0.038 (3)0.069 (3)0.023 (3)0.009 (3)0.011 (3)
C160.043 (3)0.065 (3)0.063 (3)0.031 (3)0.002 (3)0.006 (3)
C170.067 (4)0.064 (4)0.055 (3)0.033 (4)0.015 (3)0.012 (3)
C180.050 (3)0.051 (3)0.068 (3)0.033 (3)0.005 (3)0.002 (3)
Geometric parameters (Å, º) top
O1—C11.406 (8)C7—C81.547 (7)
O2—C91.473 (8)C7—C181.549 (10)
O2—C101.384 (6)C8—C91.527 (9)
C1—C21.386 (9)C9—C161.522 (9)
C1—C61.371 (10)C9—C171.527 (7)
C2—C31.393 (8)C10—C151.404 (10)
C3—C41.406 (10)C10—C111.396 (7)
C4—C51.405 (9)C11—C121.399 (9)
C4—C71.548 (7)C12—C131.388 (10)
C5—C61.395 (8)C13—C141.392 (8)
C7—C111.534 (10)C14—C151.383 (9)
O1···O1i2.911 (11)O1···O1ii2.911 (12)
C9—O2—C10118.0 (3)C7—C8—C9115.5 (5)
O1—C1—C6118.3 (6)O2—C9—C17104.8 (4)
O1—C1—C2121.3 (6)C8—C9—C16115.0 (4)
C2—C1—C6120.4 (5)C8—C9—C17109.7 (5)
C1—C2—C3119.9 (6)C16—C9—C17110.6 (5)
C2—C3—C4121.3 (6)O2—C9—C16107.4 (5)
C3—C4—C7119.8 (6)O2—C9—C8108.8 (5)
C5—C4—C7123.3 (6)O2—C10—C15114.3 (4)
C3—C4—C5116.8 (5)O2—C10—C11124.1 (6)
C4—C5—C6121.8 (6)C11—C10—C15121.6 (5)
C1—C6—C5119.7 (6)C7—C11—C12121.4 (4)
C4—C7—C11111.5 (5)C10—C11—C12116.8 (6)
C4—C7—C18108.9 (4)C7—C11—C10121.8 (5)
C8—C7—C11108.0 (4)C11—C12—C13122.6 (5)
C8—C7—C18106.6 (5)C12—C13—C14119.2 (6)
C11—C7—C18109.8 (6)C13—C14—C15120.0 (6)
C4—C7—C8111.9 (5)C10—C15—C14119.8 (5)
C10—O2—C9—C840.8 (6)C4—C7—C11—C10108.6 (6)
C10—O2—C9—C1684.3 (5)C4—C7—C11—C1273.8 (7)
C10—O2—C9—C17158.0 (5)C8—C7—C11—C1014.7 (8)
C9—O2—C10—C1114.4 (8)C8—C7—C11—C12162.9 (6)
C9—O2—C10—C15167.3 (5)C18—C7—C11—C10130.6 (6)
O1—C1—C2—C3178.6 (5)C11—C7—C8—C943.5 (7)
C2—C1—C6—C50.7 (9)C18—C7—C8—C9161.4 (5)
C6—C1—C2—C31.4 (9)C18—C7—C11—C1247.0 (7)
O1—C1—C6—C5179.2 (5)C7—C8—C9—C17171.4 (5)
C1—C2—C3—C41.2 (9)C7—C8—C9—C1663.2 (8)
C2—C3—C4—C50.3 (8)C7—C8—C9—O257.3 (6)
C2—C3—C4—C7178.8 (5)O2—C10—C11—C70.4 (9)
C3—C4—C5—C60.4 (8)C15—C10—C11—C120.9 (9)
C3—C4—C7—C11179.3 (5)O2—C10—C11—C12177.3 (5)
C3—C4—C7—C1859.4 (7)C15—C10—C11—C7178.6 (6)
C5—C4—C7—C8120.2 (6)C11—C10—C15—C140.0 (10)
C5—C4—C7—C110.9 (7)O2—C10—C15—C14178.4 (5)
C5—C4—C7—C18122.2 (6)C10—C11—C12—C131.2 (9)
C3—C4—C7—C858.2 (7)C7—C11—C12—C13178.9 (6)
C7—C4—C5—C6178.0 (5)C11—C12—C13—C140.5 (10)
C4—C5—C6—C10.2 (8)C12—C13—C14—C150.4 (10)
C4—C7—C8—C979.6 (7)C13—C14—C15—C100.7 (9)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
(DIE) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-heptanoic acid top
Crystal data top
6(C18H20O2)·(C7H14O2)Dx = 1.204 Mg m3
Mr = 1740.3Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.30 (2) Åθ = 5–25°
c = 11.07 (1) ŵ = 0.08 mm1
V = 7145 (10) Å3T = 293 K
Z = 3Acicular,hexagonal prism, colourless
F(000) = 28080.6 × 0.2 × 0.2 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.053
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ'fixed, where the angle θ' is the projection of θ on the equatorial planek = 2626
4458 measured reflectionsl = 011
1626 independent reflectionsStandard reflections: one per layer; every 20 reflections
1350 reflections with refl_obs_if_F_ > _6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.058See text
wR(F2) = 0.058 w = 1/[σ2(F) + 0.00012F2]
S = 1.28(Δ/σ)max = 0.001
1350 reflectionsΔρmax = 0.45 e Å3
215 parametersΔρmin = 0.27 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.12390 (10)0.0571 (3)0.0187 (3)0.0787 (15)
O20.26330 (10)0.1754 (2)0.6261 (2)0.0520 (11)
C10.1650 (2)0.0747 (4)0.1108 (4)0.0549 (18)
C20.1784 (2)0.0370 (4)0.1649 (4)0.0573 (19)
C30.2183 (2)0.0557 (4)0.2581 (3)0.0518 (16)
C40.2453 (2)0.1119 (4)0.2984 (3)0.0391 (15)
C50.2308 (2)0.1482 (4)0.2397 (3)0.0469 (16)
C60.1911 (2)0.1302 (4)0.1467 (3)0.0526 (16)
C70.2884 (2)0.1305 (4)0.4032 (3)0.0377 (16)
C80.2613 (2)0.0964 (4)0.5196 (3)0.0418 (16)
C90.2270 (2)0.1158 (4)0.5926 (3)0.0414 (16)
C100.2996 (2)0.2117 (4)0.5389 (3)0.0420 (16)
C110.3135 (2)0.1937 (4)0.4332 (3)0.0392 (16)
C120.3531 (2)0.2356 (4)0.3563 (3)0.0478 (16)
C130.3770 (2)0.2928 (4)0.3818 (4)0.0550 (17)
C140.3620 (2)0.3096 (4)0.4870 (4)0.0558 (17)
C150.3236 (2)0.2691 (4)0.5657 (4)0.0497 (17)
C160.1752 (2)0.1107 (4)0.5286 (4)0.0572 (17)
C170.2101 (2)0.0842 (4)0.7141 (4)0.062 (2)
C180.3365 (2)0.1189 (4)0.3683 (4)0.0544 (17)
O30.000600.016000.096100.1631*0.167
O40.041000.066900.189700.1883*0.167
C200.008900.013100.192300.1115*0.167
C210.006500.015100.314400.2211*0.167
C220.016300.026800.417300.1254*0.167
C230.017500.000100.538700.1049*0.167
C240.020500.038900.642500.1059*0.167
C250.028400.015400.762900.1235*0.167
C260.022800.043900.784100.2679*0.167
H10.128 (3)0.023 (5)0.021 (6)0.14 (3)*
H20.1581 (2)0.0065 (4)0.1353 (4)0.090 (15)*
H30.2285 (2)0.0262 (4)0.3000 (3)0.059 (12)*
H40.2509 (2)0.1920 (4)0.2680 (3)0.072 (13)*
H50.1817 (2)0.1599 (4)0.1027 (3)0.080 (14)*
H60.2338 (2)0.0527 (4)0.4946 (3)0.048 (11)*
H70.2949 (2)0.0996 (4)0.5766 (3)0.042 (10)*
H80.3655 (2)0.2231 (4)0.2745 (3)0.055 (11)*
H90.4066 (2)0.3240 (4)0.3196 (4)0.057 (11)*
H100.3805 (2)0.3540 (4)0.5082 (4)0.072 (13)*
H110.3119 (2)0.2820 (4)0.6479 (4)0.049 (10)*
H120.1475 (2)0.0672 (4)0.5030 (4)0.095 (17)*
H130.1530 (2)0.1241 (4)0.5888 (4)0.093 (15)*
H140.1882 (2)0.1369 (4)0.4488 (4)0.116 (18)*
H150.1829 (2)0.0396 (4)0.6981 (4)0.085 (15)*
H160.2476 (2)0.0911 (4)0.7614 (4)0.110 (19)*
H170.1879 (2)0.0999 (4)0.7681 (4)0.078 (14)*
H180.3568 (2)0.1419 (4)0.2869 (4)0.068 (12)*
H190.3672 (2)0.1325 (4)0.4405 (4)0.073 (13)*
H200.3189 (2)0.0741 (4)0.3529 (4)0.091 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.076 (3)0.085 (3)0.0615 (19)0.030 (2)0.018 (2)0.0116 (19)
O20.051 (2)0.044 (2)0.0561 (15)0.0201 (17)0.0072 (15)0.0067 (15)
C10.050 (4)0.059 (3)0.042 (2)0.017 (3)0.001 (3)0.000 (2)
C20.060 (4)0.039 (3)0.056 (3)0.012 (3)0.001 (3)0.011 (3)
C30.054 (3)0.043 (3)0.054 (2)0.021 (3)0.002 (2)0.001 (2)
C40.040 (3)0.033 (3)0.0387 (19)0.014 (2)0.006 (2)0.004 (2)
C50.047 (3)0.046 (3)0.046 (2)0.022 (3)0.002 (2)0.002 (2)
C60.053 (3)0.049 (3)0.051 (2)0.022 (3)0.001 (3)0.001 (2)
C70.038 (3)0.032 (3)0.045 (2)0.019 (2)0.005 (2)0.003 (2)
C80.041 (3)0.037 (3)0.052 (2)0.023 (2)0.001 (2)0.001 (2)
C90.038 (3)0.034 (3)0.047 (2)0.014 (3)0.001 (2)0.000 (2)
C100.038 (3)0.043 (3)0.046 (2)0.021 (2)0.001 (2)0.003 (2)
C110.038 (3)0.037 (3)0.043 (2)0.019 (2)0.005 (2)0.001 (2)
C120.045 (3)0.040 (3)0.050 (2)0.015 (3)0.002 (2)0.001 (2)
C130.052 (3)0.038 (3)0.065 (3)0.015 (3)0.006 (3)0.004 (3)
C140.049 (3)0.034 (3)0.082 (3)0.019 (3)0.019 (3)0.007 (3)
C150.049 (3)0.039 (3)0.065 (3)0.025 (3)0.007 (2)0.010 (3)
C160.043 (3)0.067 (3)0.065 (3)0.030 (3)0.001 (3)0.004 (3)
C170.065 (4)0.064 (4)0.055 (2)0.031 (3)0.016 (3)0.013 (3)
C180.053 (3)0.053 (3)0.066 (3)0.033 (3)0.011 (2)0.000 (3)
Geometric parameters (Å, º) top
O1—C11.411 (7)C7—C111.541 (10)
O2—C91.468 (8)C7—C81.545 (7)
O2—C101.383 (6)C8—C91.519 (9)
C1—C21.389 (9)C9—C171.539 (7)
C1—C61.372 (10)C9—C161.525 (9)
C2—C31.398 (8)C10—C111.393 (7)
C3—C41.402 (10)C10—C151.395 (10)
C4—C51.398 (9)C11—C121.402 (9)
C4—C71.546 (7)C12—C131.387 (10)
C5—C61.394 (8)C13—C141.386 (8)
C7—C181.546 (10)C14—C151.386 (9)
O1···O1i2.961 (8)O1···O1ii2.961 (7)
C9—O2—C10117.6 (3)C7—C8—C9115.3 (5)
C2—C1—C6120.7 (5)C8—C9—C17109.5 (5)
O1—C1—C6118.1 (6)C16—C9—C17110.5 (5)
O1—C1—C2121.2 (6)O2—C9—C17104.3 (4)
C1—C2—C3119.6 (6)C8—C9—C16115.2 (4)
C2—C3—C4121.4 (6)O2—C9—C16107.5 (5)
C5—C4—C7123.7 (6)O2—C9—C8109.2 (5)
C3—C4—C7119.7 (6)O2—C10—C15115.0 (4)
C3—C4—C5116.6 (5)O2—C10—C11123.9 (6)
C4—C5—C6122.6 (6)C11—C10—C15121.1 (5)
C1—C6—C5119.1 (6)C10—C11—C12117.2 (6)
C8—C7—C11107.8 (4)C7—C11—C10121.9 (5)
C11—C7—C18109.6 (6)C7—C11—C12120.8 (4)
C4—C7—C11111.6 (5)C11—C12—C13122.1 (5)
C8—C7—C18106.6 (5)C12—C13—C14119.5 (6)
C4—C7—C8111.8 (5)C13—C14—C15119.7 (6)
C4—C7—C18109.3 (4)C10—C15—C14120.4 (5)
C10—O2—C9—C842.3 (6)C4—C7—C11—C10108.8 (6)
C10—O2—C9—C1683.3 (5)C4—C7—C11—C1273.5 (7)
C10—O2—C9—C17159.3 (5)C8—C7—C11—C1014.4 (8)
C9—O2—C10—C1115.6 (8)C8—C7—C11—C12163.3 (6)
C9—O2—C10—C15166.4 (5)C18—C7—C11—C10130.0 (6)
O1—C1—C2—C3178.3 (5)C11—C7—C8—C943.0 (7)
C2—C1—C6—C50.9 (9)C18—C7—C8—C9160.6 (5)
C6—C1—C2—C30.9 (9)C18—C7—C11—C1247.7 (6)
O1—C1—C6—C5178.4 (5)C7—C8—C9—C17171.7 (5)
C1—C2—C3—C40.1 (9)C7—C8—C9—C1663.0 (8)
C2—C3—C4—C50.8 (8)C7—C8—C9—O258.0 (6)
C2—C3—C4—C7179.0 (5)O2—C10—C11—C70.9 (9)
C3—C4—C5—C60.8 (8)C15—C10—C11—C120.9 (9)
C3—C4—C7—C11179.6 (5)O2—C10—C11—C12176.9 (5)
C3—C4—C7—C1858.2 (7)C15—C10—C11—C7178.7 (6)
C5—C4—C7—C8120.2 (6)C11—C10—C15—C140.0 (10)
C5—C4—C7—C110.6 (8)O2—C10—C15—C14178.0 (5)
C5—C4—C7—C18122.0 (6)C10—C11—C12—C131.3 (9)
C3—C4—C7—C859.5 (7)C7—C11—C12—C13179.1 (6)
C7—C4—C5—C6178.9 (5)C11—C12—C13—C140.6 (10)
C4—C5—C6—C10.0 (9)C12—C13—C14—C150.4 (9)
C4—C7—C8—C980.0 (7)C13—C14—C15—C100.7 (10)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.99 (10)2.28 (9)2.961 (8)125 (7)
Symmetry code: (i) y, x+y, z.
(DIO) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-octanoic acid top
Crystal data top
6(C18H20O2)·(C8H16O2)Dx = 1.198 Mg m3
Mr = 1754.4Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.30 (2) Åθ = 5–25°
c = 11.20 (1) ŵ = 0.08 mm1
V = 7229 (10) Å3T = 293 K
Z = 3Acicular, hexagonal prism, colourless
F(000) = 28320.5 × 0.15 × 0.15 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.043
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ'fixed, where the angle θ' is the projection of θ on the equatorial planek = 2626
4242 measured reflectionsl = 011
1588 independent reflectionsStandard reflections: one per layer; every 20 reflections
1037 reflections with refl_obs_if_F_ > 6.0_σ(F) intensity decay: maximum 5% corrected by interpolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.094See text
wR(F2) = 0.085 w = 1/[σ2(F) + 0.00016F2]
S = 1.28(Δ/σ)max < 0.001
1037 reflectionsΔρmax = 0.52 e Å3
215 parametersΔρmin = 0.28 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1265 (4)0.0572 (8)0.0191 (7)0.103 (4)
O20.2637 (3)0.1757 (6)0.6255 (5)0.060 (3)
C10.1672 (5)0.0754 (11)0.1114 (10)0.074 (5)
C20.1807 (5)0.0376 (11)0.1629 (10)0.074 (5)
C30.2195 (5)0.0551 (10)0.2586 (9)0.065 (5)
C40.2466 (4)0.1117 (8)0.3016 (7)0.051 (4)
C50.2319 (4)0.1481 (9)0.2425 (8)0.058 (4)
C60.1934 (5)0.1308 (10)0.1495 (9)0.067 (5)
C70.2890 (4)0.1303 (8)0.4063 (8)0.050 (4)
C80.2612 (4)0.0967 (7)0.5205 (7)0.040 (3)
C90.2263 (4)0.1161 (8)0.5932 (8)0.048 (4)
C100.3000 (4)0.2117 (8)0.5370 (9)0.052 (4)
C110.3136 (4)0.1935 (8)0.4342 (8)0.045 (4)
C120.3531 (4)0.2356 (8)0.3585 (9)0.059 (4)
C130.3770 (4)0.2936 (8)0.3846 (10)0.063 (4)
C140.3619 (4)0.3092 (8)0.4882 (10)0.063 (5)
C150.3237 (4)0.2691 (8)0.5671 (8)0.059 (4)
C160.1757 (4)0.1112 (8)0.5278 (9)0.065 (4)
C170.2096 (5)0.0846 (10)0.7139 (8)0.066 (4)
C180.3384 (4)0.1199 (8)0.3713 (10)0.069 (4)
O30.019000.057000.170000.2914*0.167
O40.041000.035000.110000.2042*0.167
C200.006000.009000.164300.1382*0.167
C210.052000.000500.223200.2493*0.167
C220.048300.003800.359900.2712*0.167
C230.013700.033100.399200.0816*0.167
C240.017300.030700.536200.0374*0.167
C250.003700.030800.574800.2078*0.167
C260.000900.033000.711500.1134*0.167
C270.036900.012700.770400.0535*0.167
H10.144 (4)0.027 (9)0.017 (8)0.10 (4)*
H20.1613 (5)0.0055 (11)0.1312 (10)0.10 (4)*
H30.2286 (5)0.0249 (10)0.3005 (9)0.07 (3)*
H40.2515 (4)0.1917 (9)0.2707 (8)0.06 (3)*
H50.1840 (5)0.1609 (10)0.1080 (9)0.08 (3)*
H60.2336 (4)0.0529 (7)0.4961 (7)0.09 (3)*
H70.2946 (4)0.0999 (7)0.5776 (7)0.025 (19)*
H80.3654 (4)0.2229 (8)0.2777 (9)0.09 (3)*
H90.4068 (4)0.3250 (8)0.3237 (10)0.06 (3)*
H100.3804 (4)0.3537 (8)0.5086 (10)0.08 (3)*
H110.3126 (4)0.2823 (8)0.6488 (8)0.06 (3)*
H120.1475 (4)0.0675 (8)0.5033 (9)0.17 (6)*
H130.1537 (4)0.1255 (8)0.5856 (9)0.05 (3)*
H140.1894 (4)0.1369 (8)0.4482 (9)0.06 (3)*
H150.1818 (5)0.0400 (10)0.6981 (8)0.11 (4)*
H160.2471 (5)0.0909 (10)0.7597 (8)0.20 (7)*
H170.1881 (5)0.1008 (10)0.7681 (8)0.10 (4)*
H180.3584 (4)0.1428 (8)0.2906 (10)0.10 (4)*
H190.3691 (4)0.1340 (8)0.4425 (10)0.13 (5)*
H200.3215 (4)0.0752 (8)0.3566 (10)0.08 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.098 (9)0.122 (7)0.081 (5)0.048 (7)0.025 (6)0.023 (5)
O20.046 (5)0.043 (5)0.081 (4)0.014 (4)0.005 (4)0.006 (4)
C10.076 (11)0.083 (10)0.060 (7)0.037 (9)0.008 (8)0.005 (7)
C20.056 (12)0.057 (8)0.071 (7)0.000 (9)0.008 (8)0.020 (7)
C30.077 (9)0.032 (9)0.083 (7)0.024 (8)0.022 (7)0.004 (7)
C40.045 (7)0.045 (7)0.064 (6)0.023 (6)0.009 (6)0.006 (6)
C50.050 (9)0.053 (8)0.057 (6)0.016 (7)0.013 (6)0.013 (6)
C60.089 (10)0.046 (10)0.061 (7)0.031 (8)0.007 (7)0.002 (7)
C70.043 (7)0.036 (7)0.074 (6)0.023 (6)0.001 (5)0.006 (6)
C80.033 (6)0.043 (6)0.051 (5)0.025 (6)0.001 (5)0.008 (5)
C90.037 (7)0.035 (7)0.070 (6)0.017 (6)0.006 (6)0.004 (6)
C100.040 (7)0.037 (7)0.075 (7)0.016 (6)0.001 (6)0.007 (6)
C110.041 (7)0.038 (7)0.057 (6)0.020 (6)0.002 (6)0.002 (5)
C120.058 (8)0.039 (8)0.078 (7)0.022 (7)0.002 (6)0.009 (6)
C130.053 (8)0.054 (8)0.080 (7)0.025 (7)0.005 (7)0.004 (7)
C140.062 (8)0.047 (9)0.080 (7)0.028 (7)0.008 (6)0.000 (7)
C150.051 (8)0.056 (8)0.070 (7)0.026 (7)0.002 (6)0.004 (6)
C160.046 (8)0.076 (7)0.081 (7)0.037 (7)0.003 (7)0.002 (6)
C170.065 (9)0.067 (8)0.066 (6)0.032 (8)0.015 (7)0.013 (7)
C180.059 (7)0.053 (8)0.107 (8)0.038 (7)0.019 (6)0.008 (8)
Geometric parameters (Å, º) top
O1—C11.414 (18)C7—C111.54 (2)
O2—C91.470 (17)C7—C181.561 (19)
O2—C101.399 (15)C8—C91.535 (17)
C1—C61.38 (2)C9—C171.544 (15)
C1—C21.38 (2)C9—C161.509 (18)
C2—C31.41 (2)C10—C111.377 (16)
C3—C41.42 (2)C10—C151.40 (2)
C4—C71.544 (16)C11—C121.401 (18)
C4—C51.409 (18)C12—C131.41 (2)
C5—C61.384 (18)C13—C141.369 (17)
C7—C81.535 (14)C14—C151.388 (18)
O1···O1i3.03 (2)O1···O1ii3.03 (2)
C9—O2—C10117.4 (8)C7—C8—C9116.3 (10)
C2—C1—C6120.3 (14)O2—C9—C8107.8 (10)
O1—C1—C6119.8 (15)O2—C9—C17104.4 (9)
O1—C1—C2119.9 (16)C8—C9—C16114.2 (8)
C1—C2—C3119.9 (16)C8—C9—C17109.5 (11)
C2—C3—C4121.3 (14)C16—C9—C17111.9 (11)
C5—C4—C7123.8 (12)O2—C9—C16108.4 (11)
C3—C4—C7120.8 (12)C11—C10—C15123.1 (12)
C3—C4—C5115.5 (11)O2—C10—C11124.3 (12)
C4—C5—C6123.2 (13)O2—C10—C15112.5 (9)
C1—C6—C5119.8 (14)C7—C11—C10122.0 (11)
C8—C7—C18108.3 (10)C7—C11—C12121.5 (10)
C4—C7—C8111.8 (11)C10—C11—C12116.5 (13)
C4—C7—C11111.0 (10)C11—C12—C13122.0 (11)
C11—C7—C18108.8 (11)C12—C13—C14118.9 (12)
C8—C7—C11108.0 (8)C13—C14—C15121.3 (13)
C4—C7—C18108.9 (9)C10—C15—C14118.2 (10)
C10—O2—C9—C843.1 (13)C4—C7—C11—C10110.0 (13)
C10—O2—C9—C1681.0 (12)C4—C7—C11—C1272.9 (15)
C10—O2—C9—C17159.5 (11)C8—C7—C11—C1012.8 (17)
C9—O2—C10—C1117.2 (18)C8—C7—C11—C12164.3 (12)
C9—O2—C10—C15165.8 (11)C18—C7—C11—C10130.2 (12)
O1—C1—C2—C3177.2 (13)C11—C7—C8—C942.1 (14)
C2—C1—C6—C52 (2)C18—C7—C8—C9159.8 (10)
C6—C1—C2—C33 (2)C18—C7—C11—C1246.9 (14)
O1—C1—C6—C5177.9 (12)C7—C8—C9—C17170.9 (11)
C1—C2—C3—C42 (2)C7—C8—C9—C1662.6 (15)
C2—C3—C4—C50.1 (19)C7—C8—C9—O257.9 (12)
C2—C3—C4—C7179.9 (12)O2—C10—C11—C71 (2)
C3—C4—C5—C60.6 (18)C15—C10—C11—C120.0 (19)
C3—C4—C7—C11178.6 (11)O2—C10—C11—C12176.6 (12)
C3—C4—C7—C1858.9 (15)C15—C10—C11—C7177.2 (12)
C5—C4—C7—C8119.2 (13)C11—C10—C15—C141 (2)
C5—C4—C7—C111.4 (16)O2—C10—C15—C14178.1 (11)
C5—C4—C7—C18121.2 (13)C10—C11—C12—C131.2 (19)
C3—C4—C7—C860.8 (15)C7—C11—C12—C13178.4 (12)
C7—C4—C5—C6179.3 (12)C11—C12—C13—C141 (2)
C4—C5—C6—C10 (2)C12—C13—C14—C150 (2)
C4—C7—C8—C980.3 (13)C13—C14—C15—C101.0 (19)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i1.14 (14)2.54 (14)3.03 (2)104 (8)
Symmetry code: (i) y, x+y, z.
(DIT) [4-p-hydroxyphenyl-2,2,4-trimethylchroman]-trifluoroacetic acid top
Crystal data top
3(C18H20O2)·(C2F3O2)Dx = 1.287 Mg m3
Mr = 919.02Melting point: not measured K
Trigonal, R3Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -R 3Cell parameters from 15 reflections
a = 27.19 (2) Åθ = 5–22.5°
c = 11.097 (10) ŵ = 0.09 mm1
V = 7105 (10) Å3T = 293 K
Z = 6Acicular, hexagonal prism, colourless
F(000) = 29280.40 × 0.12 × 0.12 mm
Data collection top
Stoe STADI-2 two circle
diffractometer
Rint = 0.109
Radiation source: fine focus sealed tubeθmax = 22.5°, θmin = 1.5°
Graphite monochromatorh = 2626
variable ω scan 2θ' fixed, where the angle θ' is the projection of θ on the equatorial planek = 2526
4176 measured reflectionsl = 011
1521 independent reflectionsStandard reflections: one per layer; every 20 reflections
1013 reflections with refl_obs_if_F_ > _6.0_σ(F) intensity decay: maximum 5% corrected by intepolation
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.091See text
wR(F2) = 0.083 w = 1/[σ2(F) + 0.00019F2]
S = 1.81(Δ/σ)max = 0.001
1013 reflectionsΔρmax = 0.58 e Å3
215 parametersΔρmin = 0.32 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. See text

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1229 (4)0.0575 (8)0.0181 (8)0.085 (4)
O20.2624 (2)0.1751 (4)0.6242 (5)0.057 (2)
C10.1638 (4)0.0736 (8)0.1079 (8)0.057 (4)
C20.1768 (4)0.0358 (8)0.1633 (8)0.057 (4)
C30.2169 (4)0.0549 (8)0.2557 (7)0.053 (3)
C40.2446 (3)0.1116 (7)0.2969 (7)0.048 (3)
C50.2301 (4)0.1481 (8)0.2388 (7)0.047 (3)
C60.1901 (4)0.1294 (8)0.1474 (7)0.050 (4)
C70.2880 (3)0.1302 (6)0.4021 (7)0.044 (3)
C80.2609 (4)0.0962 (7)0.5196 (6)0.047 (3)
C90.2254 (4)0.1147 (8)0.5916 (7)0.048 (3)
C100.2989 (3)0.2110 (7)0.5360 (8)0.048 (3)
C110.3126 (4)0.1929 (7)0.4309 (7)0.045 (3)
C120.3523 (4)0.2351 (8)0.3559 (8)0.058 (4)
C130.3765 (4)0.2920 (8)0.3827 (8)0.058 (4)
C140.3616 (4)0.3094 (8)0.4872 (8)0.064 (4)
C150.3229 (4)0.2685 (8)0.5662 (8)0.059 (4)
C160.1733 (4)0.1087 (8)0.5292 (8)0.062 (4)
C170.2099 (4)0.0837 (8)0.7142 (7)0.067 (4)
C180.3360 (3)0.1188 (7)0.3643 (8)0.057 (3)
F10.0099 (15)0.039 (2)0.411 (3)0.275 (18)*0.333
F20.0281 (15)0.044 (2)0.239 (3)0.156 (8)*0.333
F30.0645 (15)0.037 (2)0.339 (3)0.144 (8)*0.333
O30.0166 (15)0.052 (2)0.292 (3)0.72 (9)*0.333
O40.0107 (15)0.025 (2)0.133 (3)0.34 (3)*0.333
C200.0236 (15)0.005 (2)0.242 (3)0.25 (3)*0.333
C210.0161 (15)0.011 (2)0.310 (3)0.34 (3)*0.333
H10.114 (3)0.030 (6)0.027 (6)0.00 (2)*
H20.1560 (4)0.0081 (8)0.1359 (8)0.18 (5)*
H30.2275 (4)0.0255 (8)0.2972 (7)0.07 (3)*
H40.2502 (4)0.1920 (8)0.2661 (7)0.09 (3)*
H50.1800 (4)0.1591 (8)0.1054 (7)0.06 (2)*
H60.2337 (4)0.0522 (7)0.4946 (6)0.07 (3)*
H70.2947 (4)0.0999 (7)0.5769 (6)0.05 (2)*
H80.3652 (4)0.2229 (8)0.2744 (8)0.038 (19)*
H90.4067 (4)0.3236 (8)0.3217 (8)0.04 (2)*
H100.3797 (4)0.3540 (8)0.5077 (8)0.07 (3)*
H110.3116 (4)0.2810 (8)0.6494 (8)0.07 (2)*
H120.1457 (4)0.0649 (8)0.5042 (8)0.11 (4)*
H130.1510 (4)0.1221 (8)0.5895 (8)0.06 (2)*
H140.1860 (4)0.1350 (8)0.4494 (8)0.13 (4)*
H150.1825 (4)0.0386 (8)0.7007 (7)0.14 (4)*
H160.2483 (4)0.0913 (8)0.7590 (7)0.08 (3)*
H170.1883 (4)0.0998 (8)0.7692 (7)0.08 (3)*
H180.3559 (3)0.1423 (7)0.2831 (8)0.08 (3)*
H190.3674 (3)0.1321 (7)0.4352 (8)0.05 (2)*
H200.3182 (3)0.0740 (7)0.3477 (8)0.09 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.071 (7)0.065 (6)0.111 (6)0.027 (6)0.022 (5)0.007 (5)
O20.048 (5)0.043 (4)0.074 (3)0.018 (4)0.010 (3)0.008 (3)
C10.043 (8)0.055 (7)0.070 (6)0.023 (6)0.003 (6)0.004 (5)
C20.044 (8)0.047 (7)0.071 (5)0.015 (6)0.005 (6)0.000 (5)
C30.042 (7)0.038 (6)0.079 (5)0.021 (6)0.003 (5)0.000 (5)
C40.031 (7)0.034 (6)0.074 (5)0.013 (5)0.010 (5)0.005 (5)
C50.037 (7)0.033 (6)0.069 (5)0.015 (5)0.001 (5)0.000 (5)
C60.047 (7)0.038 (7)0.066 (5)0.021 (6)0.001 (5)0.000 (5)
C70.028 (6)0.029 (6)0.075 (5)0.014 (5)0.008 (5)0.005 (5)
C80.046 (6)0.037 (6)0.065 (5)0.025 (5)0.004 (5)0.006 (5)
C90.038 (6)0.028 (6)0.074 (5)0.013 (6)0.003 (5)0.008 (5)
C100.028 (6)0.040 (6)0.080 (6)0.021 (5)0.004 (5)0.006 (5)
C110.033 (6)0.025 (6)0.071 (5)0.011 (5)0.004 (5)0.002 (5)
C120.050 (7)0.030 (7)0.087 (6)0.015 (6)0.004 (5)0.003 (6)
C130.038 (7)0.037 (6)0.086 (6)0.009 (6)0.000 (6)0.007 (5)
C140.058 (7)0.039 (8)0.096 (7)0.026 (6)0.017 (6)0.012 (6)
C150.043 (7)0.047 (7)0.091 (7)0.025 (6)0.000 (6)0.008 (6)
C160.048 (7)0.053 (7)0.092 (7)0.031 (6)0.007 (6)0.010 (6)
C170.067 (8)0.056 (8)0.072 (6)0.027 (7)0.014 (6)0.013 (6)
C180.036 (6)0.045 (6)0.090 (6)0.021 (6)0.006 (5)0.001 (6)
Geometric parameters (Å, º) top
O1—C11.391 (16)C7—C111.522 (15)
O2—C101.388 (12)C7—C181.543 (14)
O2—C91.479 (16)C8—C91.519 (17)
C1—C21.387 (18)C9—C171.544 (14)
C1—C61.386 (19)C9—C161.511 (18)
C2—C31.394 (16)C10—C111.387 (13)
C3—C41.411 (18)C10—C151.401 (18)
C4—C51.395 (17)C11—C121.391 (16)
C4—C71.554 (13)C12—C131.38 (2)
C5—C61.385 (16)C13—C141.387 (15)
C7—C81.555 (12)C14—C151.394 (17)
O1···O1i2.92 (2)O1···O1ii2.92 (2)
C9—O2—C10117.3 (7)C7—C8—C9115.8 (9)
O1—C1—C2123.0 (13)O2—C9—C17103.8 (8)
C2—C1—C6119.2 (11)C8—C9—C16116.1 (8)
O1—C1—C6117.7 (12)C8—C9—C17109.1 (10)
C1—C2—C3119.5 (12)C16—C9—C17111.1 (10)
C2—C3—C4122.4 (12)O2—C9—C8107.7 (10)
C3—C4—C7120.2 (9)O2—C9—C16108.2 (10)
C5—C4—C7123.7 (10)O2—C10—C15112.7 (8)
C3—C4—C5116.2 (9)O2—C10—C11124.6 (10)
C4—C5—C6121.8 (12)C11—C10—C15122.6 (10)
C1—C6—C5121.0 (12)C10—C11—C12116.5 (11)
C4—C7—C18108.1 (7)C7—C11—C10121.9 (9)
C8—C7—C11107.6 (7)C7—C11—C12121.6 (9)
C4—C7—C11111.1 (8)C11—C12—C13122.4 (10)
C11—C7—C18109.9 (9)C12—C13—C14120.4 (11)
C8—C7—C18107.8 (8)C13—C14—C15119.1 (13)
C4—C7—C8112.3 (8)C10—C15—C14119.0 (10)
C10—O2—C9—C842.3 (11)C4—C7—C11—C10109.3 (11)
C10—O2—C9—C1684.0 (10)C4—C7—C11—C1274.0 (13)
C10—O2—C9—C17157.9 (9)C8—C7—C11—C1014.0 (14)
C9—O2—C10—C1115.3 (15)C8—C7—C11—C12162.7 (11)
C9—O2—C10—C15167.2 (10)C18—C7—C11—C10131.1 (11)
O1—C1—C2—C3177.7 (11)C11—C7—C8—C944.1 (12)
C2—C1—C6—C51.8 (18)C18—C7—C8—C9162.5 (9)
C6—C1—C2—C31.4 (17)C18—C7—C11—C1245.6 (13)
O1—C1—C6—C5178.2 (11)C7—C8—C9—C17170.9 (9)
C1—C2—C3—C40.9 (17)C7—C8—C9—C1662.7 (14)
C2—C3—C4—C50.7 (16)C7—C8—C9—O258.8 (10)
C2—C3—C4—C7178.7 (10)O2—C10—C11—C70.1 (18)
C3—C4—C5—C61.1 (16)C15—C10—C11—C120.5 (17)
C3—C4—C7—C11179.8 (9)O2—C10—C11—C12176.7 (10)
C3—C4—C7—C1859.2 (12)C15—C10—C11—C7177.4 (10)
C5—C4—C7—C8119.7 (11)C11—C10—C15—C140.8 (18)
C5—C4—C7—C110.8 (13)O2—C10—C15—C14178.4 (10)
C5—C4—C7—C18121.5 (11)C10—C11—C12—C130.8 (18)
C3—C4—C7—C859.7 (12)C7—C11—C12—C13177.7 (11)
C7—C4—C5—C6178.3 (10)C11—C12—C13—C140 (2)
C4—C5—C6—C11.6 (17)C12—C13—C14—C151.6 (19)
C4—C7—C8—C978.4 (11)C13—C14—C15—C101.9 (18)
Symmetry codes: (i) y, x+y, z; (ii) xy, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.67 (9)2.31 (9)2.92 (2)153 (9)
Symmetry code: (i) y, x+y, z.
 

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