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,
, 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
| 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 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIFsup2.hkl Contains datablock DIF |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIAsup3.hkl Contains datablock DIA |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIPsup4.hkl Contains datablock DIP |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIBsup5.hkl Contains datablock DIB |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIIsup6.hkl Contains datablock DII |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIVsup7.hkl Contains datablock DIV |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIHsup8.hkl Contains datablock DIH |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIEsup9.hkl Contains datablock DIE |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768102022395/bm0059DIOsup10.hkl Contains datablock DIO |
| 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
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 m−3 |
Mr = 851.01 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.19 (2) Å | θ = 5–25° |
c = 11.02 (1) Å | µ = 0.08 mm−1 |
V = 7056 (10) Å3 | T = 293 K |
Z = 6 | Acicular, hexagonal prism, colourless |
F(000) = 2736 | 0.6 × 0.2 × 0.2 mm |
Data collection top
Stoe STADI-2 two-circle diffractometer | Rint = 0.080 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ' fixed, where the angle θ' is the projection
of θ on the equatorial plane | k = −26→26 |
4175 measured reflections | l = 0→11 |
1572 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.052 | See text |
wR(F2) = 0.082 | w = 1/[σ2 (F) + 0.00018F2] |
S = 1.15 | (Δ/σ)max = 0.01 |
1285 reflections | Δρmax = 0.27 e Å−3 |
215 parameters | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.11790 (10) | 0.0542 (2) | 0.0210 (2) | 0.0662 (11) | |
O2 | 0.26080 (10) | 0.1740 (2) | 0.6258 (2) | 0.0540 (10) | |
C1 | 0.1600 (2) | 0.0723 (4) | 0.1105 (3) | 0.0467 (16) | |
C2 | 0.1743 (2) | 0.0347 (4) | 0.1642 (3) | 0.0498 (16) | |
C3 | 0.2152 (2) | 0.0538 (4) | 0.2555 (3) | 0.0481 (15) | |
C4 | 0.2436 (2) | 0.1107 (4) | 0.2959 (3) | 0.0398 (15) | |
C5 | 0.2292 (2) | 0.1475 (4) | 0.2377 (3) | 0.0449 (15) | |
C6 | 0.1879 (2) | 0.1289 (4) | 0.1458 (3) | 0.0478 (16) | |
C7 | 0.2871 (2) | 0.1296 (3) | 0.4010 (3) | 0.0391 (11) | |
C8 | 0.2599 (2) | 0.0952 (4) | 0.5194 (3) | 0.0434 (13) | |
C9 | 0.2249 (2) | 0.1139 (4) | 0.5936 (3) | 0.0438 (16) | |
C10 | 0.2978 (2) | 0.2104 (4) | 0.5386 (3) | 0.0421 (12) | |
C11 | 0.3122 (2) | 0.1925 (3) | 0.4314 (3) | 0.0398 (12) | |
C12 | 0.3525 (2) | 0.2349 (4) | 0.3549 (3) | 0.0493 (16) | |
C13 | 0.3768 (2) | 0.2925 (4) | 0.3816 (4) | 0.0551 (17) | |
C14 | 0.3614 (2) | 0.3092 (4) | 0.4884 (4) | 0.0549 (17) | |
C15 | 0.3222 (2) | 0.2680 (4) | 0.5669 (3) | 0.0520 (17) | |
C16 | 0.1721 (2) | 0.1077 (4) | 0.5291 (3) | 0.0564 (16) | |
C17 | 0.2087 (2) | 0.0831 (4) | 0.7150 (3) | 0.0606 (16) | |
C18 | 0.3351 (2) | 0.1176 (4) | 0.3645 (3) | 0.0539 (16) | |
C19 | 0.00000 | 0.00000 | 0.29900 | 0.3062* | |
O3 | 0.04270 | 0.02920 | 0.38340 | 0.2162* | 0.333 |
O4 | −0.04920 | −0.02460 | 0.32140 | 0.4698* | 0.333 |
H1 | 0.098 (3) | 0.014 (7) | 0.022 (7) | 0.20 (4)* | |
H2 | 0.1536 (2) | −0.0091 (4) | 0.1354 (3) | 0.080 (13)* | |
H3 | 0.2256 (2) | 0.0240 (4) | 0.2966 (3) | 0.062 (11)* | |
H4 | 0.2503 (2) | 0.1916 (4) | 0.2647 (3) | 0.077 (12)* | |
H5 | 0.1784 (2) | 0.1587 (4) | 0.1022 (3) | 0.061 (11)* | |
H6 | 0.2328 (2) | 0.0512 (4) | 0.4944 (3) | 0.053 (10)* | |
H7 | 0.2938 (2) | 0.0989 (4) | 0.5767 (3) | 0.040 (9)* | |
H8 | 0.3652 (2) | 0.2225 (4) | 0.2729 (3) | 0.054 (10)* | |
H9 | 0.4069 (2) | 0.3241 (4) | 0.3201 (4) | 0.067 (11)* | |
H10 | 0.3799 (2) | 0.3536 (4) | 0.5104 (4) | 0.068 (11)* | |
H11 | 0.3106 (2) | 0.2808 (4) | 0.6499 (3) | 0.069 (11)* | |
H12 | 0.1445 (2) | 0.0638 (4) | 0.5040 (3) | 0.097 (15)* | |
H13 | 0.1498 (2) | 0.1211 (4) | 0.5894 (3) | 0.097 (14)* | |
H14 | 0.1849 (2) | 0.1338 (4) | 0.4486 (3) | 0.099 (15)* | |
H15 | 0.1818 (2) | 0.0380 (4) | 0.7001 (3) | 0.081 (14)* | |
H16 | 0.2467 (2) | 0.0908 (4) | 0.7622 (3) | 0.098 (16)* | |
H17 | 0.1862 (2) | 0.0986 (4) | 0.7689 (3) | 0.082 (13)* | |
H18 | 0.3552 (2) | 0.1406 (4) | 0.2825 (3) | 0.070 (11)* | |
H19 | 0.3662 (2) | 0.1311 (4) | 0.4363 (3) | 0.062 (11)* | |
H20 | 0.3173 (2) | 0.0726 (4) | 0.3489 (3) | 0.098 (15)* | |
H21 | 0.01500 | 0.00250 | 0.20600 | 0.0071* | 0.333 |
H22 | 0.03110 | 0.02920 | 0.47710 | 0.0658* | 0.333 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.063 (2) | 0.064 (2) | 0.0652 (16) | 0.027 (2) | −0.0198 (15) | −0.0125 (16) |
O2 | 0.0545 (19) | 0.0410 (19) | 0.0610 (14) | 0.0197 (16) | 0.0082 (13) | −0.0057 (14) |
C1 | 0.043 (3) | 0.043 (3) | 0.048 (2) | 0.017 (2) | −0.002 (2) | −0.002 (2) |
C2 | 0.058 (3) | 0.037 (3) | 0.052 (2) | 0.022 (3) | −0.004 (2) | −0.004 (2) |
C3 | 0.056 (3) | 0.041 (3) | 0.0484 (19) | 0.025 (2) | 0.002 (2) | 0.003 (2) |
C4 | 0.043 (3) | 0.032 (3) | 0.0434 (18) | 0.018 (2) | 0.0055 (19) | −0.0001 (18) |
C5 | 0.047 (3) | 0.035 (3) | 0.0493 (19) | 0.018 (2) | 0.000 (2) | −0.001 (2) |
C6 | 0.054 (3) | 0.042 (3) | 0.050 (2) | 0.026 (2) | −0.003 (2) | 0.002 (2) |
C7 | 0.039 (2) | 0.034 (2) | 0.0479 (18) | 0.021 (2) | 0.0031 (18) | 0.0010 (18) |
C8 | 0.045 (2) | 0.041 (3) | 0.0476 (18) | 0.024 (2) | −0.0012 (19) | −0.0006 (19) |
C9 | 0.043 (3) | 0.034 (3) | 0.054 (2) | 0.019 (2) | 0.0005 (19) | −0.002 (2) |
C10 | 0.035 (2) | 0.033 (2) | 0.057 (2) | 0.016 (2) | −0.002 (2) | 0.003 (2) |
C11 | 0.036 (2) | 0.036 (2) | 0.050 (2) | 0.020 (2) | −0.0026 (19) | 0.0017 (19) |
C12 | 0.043 (3) | 0.043 (3) | 0.056 (2) | 0.017 (2) | −0.001 (2) | 0.002 (2) |
C13 | 0.051 (3) | 0.034 (3) | 0.068 (3) | 0.012 (3) | −0.008 (2) | 0.005 (2) |
C14 | 0.050 (3) | 0.034 (3) | 0.078 (3) | 0.019 (3) | −0.016 (2) | −0.007 (2) |
C15 | 0.048 (3) | 0.040 (3) | 0.072 (3) | 0.025 (2) | −0.007 (2) | −0.009 (2) |
C16 | 0.048 (3) | 0.063 (3) | 0.064 (2) | 0.032 (2) | 0.002 (2) | −0.003 (2) |
C17 | 0.069 (3) | 0.062 (3) | 0.055 (2) | 0.036 (3) | 0.012 (2) | 0.013 (2) |
C18 | 0.048 (3) | 0.054 (3) | 0.067 (2) | 0.031 (2) | 0.005 (2) | 0.001 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.401 (6) | C7—C11 | 1.528 (7) |
O2—C9 | 1.468 (8) | C7—C18 | 1.548 (9) |
O2—C10 | 1.385 (6) | C8—C9 | 1.522 (9) |
C1—C2 | 1.394 (9) | C9—C16 | 1.534 (9) |
C1—C6 | 1.388 (10) | C9—C17 | 1.522 (6) |
C2—C3 | 1.393 (8) | C10—C11 | 1.406 (6) |
C3—C4 | 1.412 (10) | C10—C15 | 1.397 (10) |
C4—C7 | 1.548 (7) | C11—C12 | 1.406 (8) |
C4—C5 | 1.399 (9) | C12—C13 | 1.393 (10) |
C5—C6 | 1.405 (8) | C13—C14 | 1.399 (8) |
C7—C8 | 1.560 (6) | C14—C15 | 1.395 (9) |
| | | |
O1···O1i | 2.817 (6) | O1···O1ii | 2.817 (6) |
| | | |
C9—O2—C10 | 118.0 (3) | C7—C8—C9 | 115.9 (5) |
O1—C1—C2 | 121.3 (6) | O2—C9—C8 | 108.8 (5) |
O1—C1—C6 | 119.0 (5) | C16—C9—C17 | 110.5 (5) |
C2—C1—C6 | 119.7 (5) | O2—C9—C17 | 104.4 (4) |
C1—C2—C3 | 119.8 (6) | C8—C9—C16 | 114.9 (4) |
C2—C3—C4 | 122.2 (6) | C8—C9—C17 | 110.2 (5) |
C3—C4—C5 | 116.3 (5) | O2—C9—C16 | 107.4 (5) |
C5—C4—C7 | 123.1 (6) | O2—C10—C11 | 124.3 (6) |
C3—C4—C7 | 120.5 (5) | O2—C10—C15 | 114.5 (4) |
C4—C5—C6 | 122.1 (6) | C11—C10—C15 | 121.2 (5) |
C1—C6—C5 | 119.8 (6) | C7—C11—C10 | 121.7 (4) |
C4—C7—C18 | 108.7 (4) | C10—C11—C12 | 117.2 (5) |
C11—C7—C18 | 109.9 (5) | C7—C11—C12 | 121.0 (4) |
C4—C7—C11 | 112.0 (4) | C11—C12—C13 | 122.2 (4) |
C8—C7—C18 | 106.7 (4) | C12—C13—C14 | 119.5 (6) |
C4—C7—C8 | 111.9 (5) | C13—C14—C15 | 119.6 (6) |
C8—C7—C11 | 107.5 (4) | C10—C15—C14 | 120.4 (5) |
| | | |
C10—O2—C9—C8 | 40.3 (6) | C4—C7—C11—C10 | 108.3 (5) |
C10—O2—C9—C16 | −84.7 (5) | C4—C7—C11—C12 | −74.2 (7) |
C10—O2—C9—C17 | 158.0 (5) | C8—C7—C11—C10 | −15.0 (7) |
C9—O2—C10—C11 | −14.0 (8) | C8—C7—C11—C12 | 162.6 (5) |
C9—O2—C10—C15 | 168.1 (5) | C18—C7—C11—C10 | −130.8 (5) |
O1—C1—C2—C3 | −178.1 (5) | C11—C7—C8—C9 | 43.8 (7) |
C2—C1—C6—C5 | −1.8 (8) | C18—C7—C8—C9 | 161.7 (5) |
C6—C1—C2—C3 | 2.0 (8) | C18—C7—C11—C12 | 46.8 (6) |
O1—C1—C6—C5 | 178.3 (5) | C7—C8—C9—C17 | −171.3 (5) |
C1—C2—C3—C4 | −0.6 (8) | C7—C8—C9—C16 | 63.1 (7) |
C2—C3—C4—C5 | −1.1 (8) | C7—C8—C9—O2 | −57.4 (5) |
C2—C3—C4—C7 | 177.6 (5) | O2—C10—C11—C7 | 0.5 (9) |
C3—C4—C5—C6 | 1.3 (8) | C15—C10—C11—C12 | 0.7 (9) |
C3—C4—C7—C11 | −179.2 (5) | O2—C10—C11—C12 | −177.1 (5) |
C3—C4—C7—C18 | 59.1 (6) | C15—C10—C11—C7 | 178.3 (5) |
C5—C4—C7—C8 | 120.2 (6) | C11—C10—C15—C14 | 0.4 (9) |
C5—C4—C7—C11 | −0.6 (7) | O2—C10—C15—C14 | 178.3 (5) |
C5—C4—C7—C18 | −122.3 (6) | C10—C11—C12—C13 | −1.2 (9) |
C3—C4—C7—C8 | −58.5 (7) | C7—C11—C12—C13 | −178.8 (5) |
C7—C4—C5—C6 | −177.4 (5) | C11—C12—C13—C14 | 0.7 (9) |
C4—C5—C6—C1 | 0.1 (8) | C12—C13—C14—C15 | 0.3 (9) |
C4—C7—C8—C9 | −79.5 (6) | C13—C14—C15—C10 | −0.9 (9) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
(DIA) [4-
p-hydroxyphenyl-2,2,4-trimethylchroman]-acetic acid
top
Crystal data top
3(C18H20O2)·(C2H4O2) | Dx = 1.216 Mg m−3 |
Mr = 865.14 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.19 (2) Å | θ = 5–22.5° |
c = 11.06 (1) Å | µ = 0.08 mm−1 |
V = 7081 (10) Å3 | T = 293 K |
Z = 6 | Acicular, hexagonal prism, colourless |
F(000) = 2778 | 0.5 × 0.15 × 0.15 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.047 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ' fixed, where the angle θ'is the projection
of θ on the equatorial plane | k = −26→26 |
4483 measured reflections | l = 0→11 |
1535 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.064 | See text |
wR(F2) = 0.082 | w = 1/[σ2(F) + 0.0002F2] |
S = 1.45 | (Δ/σ)max = 0.002 |
1165 reflections | Δρmax = 0.42 e Å−3 |
215 parameters | Δρmin = −0.38 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1221 (2) | 0.0565 (4) | 0.0173 (4) | 0.0641 (19) | |
O2 | 0.2613 (2) | 0.1741 (4) | 0.6248 (3) | 0.0540 (16) | |
C1 | 0.1627 (2) | 0.0732 (5) | 0.1092 (4) | 0.045 (2) | |
C2 | 0.1757 (2) | 0.0355 (5) | 0.1636 (5) | 0.050 (2) | |
C3 | 0.2157 (2) | 0.0540 (4) | 0.2562 (4) | 0.048 (2) | |
C4 | 0.2438 (2) | 0.1106 (4) | 0.2973 (4) | 0.040 (2) | |
C5 | 0.2296 (2) | 0.1477 (4) | 0.2377 (4) | 0.044 (2) | |
C6 | 0.1894 (2) | 0.1293 (4) | 0.1445 (4) | 0.045 (2) | |
C7 | 0.2872 (2) | 0.1292 (4) | 0.4018 (4) | 0.038 (2) | |
C8 | 0.2594 (2) | 0.0944 (4) | 0.5181 (4) | 0.043 (2) | |
C9 | 0.2245 (2) | 0.1140 (4) | 0.5919 (4) | 0.043 (2) | |
C10 | 0.2981 (2) | 0.2102 (4) | 0.5378 (4) | 0.044 (2) | |
C11 | 0.3124 (2) | 0.1925 (4) | 0.4316 (4) | 0.040 (2) | |
C12 | 0.3528 (2) | 0.2351 (4) | 0.3571 (4) | 0.048 (2) | |
C13 | 0.3770 (3) | 0.2927 (6) | 0.3819 (5) | 0.055 (2) | |
C14 | 0.3619 (3) | 0.3096 (6) | 0.4876 (5) | 0.056 (2) | |
C15 | 0.3227 (3) | 0.2684 (5) | 0.5657 (5) | 0.053 (2) | |
C16 | 0.1721 (2) | 0.1082 (4) | 0.5282 (5) | 0.056 (2) | |
C17 | 0.2078 (3) | 0.0823 (6) | 0.7118 (4) | 0.059 (3) | |
C18 | 0.3356 (2) | 0.1176 (4) | 0.3657 (5) | 0.051 (2) | |
O3 | 0.04910 | 0.03100 | 0.37930 | 0.1509* | 0.333 |
O4 | −0.04650 | −0.02470 | 0.35970 | 0.2485* | 0.333 |
C21 | 0.00510 | 0.00740 | 0.17460 | 0.1668* | 0.333 |
C20 | 0.00080 | 0.00350 | 0.31430 | 0.2054* | 0.667 |
H1 | 0.109 (3) | 0.023 (7) | 0.008 (7) | 0.12 (4)* | |
H2 | 0.1550 (2) | −0.0083 (5) | 0.1350 (5) | 0.062 (16)* | |
H3 | 0.2258 (2) | 0.0242 (4) | 0.2978 (4) | 0.046 (14)* | |
H4 | 0.2504 (2) | 0.1916 (4) | 0.2655 (4) | 0.085 (19)* | |
H5 | 0.1799 (2) | 0.1591 (4) | 0.1009 (4) | 0.046 (14)* | |
H6 | 0.2318 (2) | 0.0506 (4) | 0.4926 (4) | 0.070 (17)* | |
H7 | 0.2930 (2) | 0.0975 (4) | 0.5755 (4) | 0.054 (15)* | |
H8 | 0.3657 (2) | 0.2226 (4) | 0.2758 (4) | 0.053 (14)* | |
H9 | 0.4072 (3) | 0.3242 (6) | 0.3204 (5) | 0.053 (14)* | |
H10 | 0.3802 (3) | 0.3541 (6) | 0.5091 (5) | 0.083 (19)* | |
H11 | 0.3114 (3) | 0.2812 (5) | 0.6488 (5) | 0.051 (14)* | |
H12 | 0.1444 (2) | 0.0643 (4) | 0.5031 (5) | 0.11 (2)* | |
H13 | 0.1498 (2) | 0.1216 (4) | 0.5884 (5) | 0.11 (2)* | |
H14 | 0.1849 (2) | 0.1343 (4) | 0.4481 (5) | 0.11 (2)* | |
H15 | 0.1805 (3) | 0.0375 (6) | 0.6953 (4) | 0.08 (2)* | |
H16 | 0.2455 (3) | 0.0891 (6) | 0.7587 (4) | 0.10 (2)* | |
H17 | 0.1856 (3) | 0.0979 (6) | 0.7664 (4) | 0.09 (2)* | |
H18 | 0.3560 (2) | 0.1410 (4) | 0.2845 (5) | 0.12 (2)* | |
H19 | 0.3664 (2) | 0.1310 (4) | 0.4379 (5) | 0.044 (13)* | |
H20 | 0.3180 (2) | 0.0727 (4) | 0.3496 (5) | 0.073 (18)* | |
H22 | 0.04910 | 0.03340 | 0.14850 | 0.4679* | 0.333 |
H23 | −0.01160 | −0.03460 | 0.13710 | 0.1907* | 0.333 |
H24 | −0.01900 | 0.02620 | 0.14090 | 0.2025* | 0.333 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.063 (4) | 0.061 (3) | 0.063 (3) | 0.027 (3) | −0.016 (2) | −0.006 (2) |
O2 | 0.055 (3) | 0.043 (3) | 0.058 (2) | 0.020 (3) | 0.007 (2) | −0.008 (2) |
C1 | 0.044 (5) | 0.045 (4) | 0.035 (3) | 0.015 (4) | −0.007 (3) | −0.004 (3) |
C2 | 0.057 (5) | 0.036 (4) | 0.048 (3) | 0.017 (4) | 0.001 (3) | 0.003 (3) |
C3 | 0.055 (4) | 0.038 (4) | 0.052 (3) | 0.025 (4) | −0.005 (3) | −0.002 (3) |
C4 | 0.046 (4) | 0.036 (4) | 0.040 (3) | 0.022 (3) | 0.005 (3) | 0.002 (3) |
C5 | 0.040 (4) | 0.035 (4) | 0.053 (3) | 0.015 (3) | −0.001 (3) | −0.001 (3) |
C6 | 0.049 (4) | 0.043 (4) | 0.047 (3) | 0.025 (4) | −0.004 (3) | −0.001 (3) |
C7 | 0.038 (4) | 0.036 (4) | 0.043 (3) | 0.021 (3) | 0.000 (3) | −0.002 (3) |
C8 | 0.045 (4) | 0.040 (4) | 0.050 (3) | 0.026 (3) | −0.005 (3) | 0.001 (3) |
C9 | 0.047 (4) | 0.033 (4) | 0.048 (3) | 0.020 (4) | 0.003 (3) | −0.002 (3) |
C10 | 0.035 (4) | 0.036 (4) | 0.059 (3) | 0.017 (3) | −0.001 (3) | 0.003 (3) |
C11 | 0.038 (4) | 0.037 (4) | 0.043 (3) | 0.018 (3) | −0.006 (3) | −0.006 (3) |
C12 | 0.044 (4) | 0.040 (4) | 0.052 (3) | 0.015 (4) | 0.002 (3) | 0.005 (3) |
C13 | 0.054 (4) | 0.036 (4) | 0.064 (4) | 0.015 (4) | −0.005 (4) | 0.007 (3) |
C14 | 0.054 (4) | 0.034 (4) | 0.076 (4) | 0.019 (4) | −0.020 (4) | −0.007 (4) |
C15 | 0.053 (4) | 0.042 (4) | 0.069 (4) | 0.028 (4) | −0.008 (3) | −0.008 (3) |
C16 | 0.046 (4) | 0.051 (4) | 0.072 (4) | 0.026 (4) | −0.001 (3) | −0.001 (3) |
C17 | 0.069 (5) | 0.057 (5) | 0.053 (3) | 0.033 (4) | 0.010 (3) | 0.010 (3) |
C18 | 0.047 (4) | 0.051 (4) | 0.064 (3) | 0.031 (4) | −0.004 (3) | −0.005 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.399 (9) | C7—C11 | 1.537 (10) |
O2—C9 | 1.473 (10) | C7—C18 | 1.551 (10) |
O2—C10 | 1.381 (8) | C8—C9 | 1.535 (9) |
C1—C2 | 1.378 (11) | C9—C17 | 1.522 (8) |
C1—C6 | 1.378 (11) | C9—C16 | 1.525 (9) |
C2—C3 | 1.392 (9) | C10—C15 | 1.410 (12) |
C3—C4 | 1.408 (10) | C10—C11 | 1.396 (8) |
C4—C5 | 1.411 (9) | C11—C12 | 1.398 (9) |
C4—C7 | 1.545 (8) | C12—C13 | 1.389 (12) |
C5—C6 | 1.400 (8) | C13—C14 | 1.391 (10) |
C7—C8 | 1.551 (8) | C14—C15 | 1.394 (12) |
| | | |
O1···O1i | 2.903 (12) | O1···O1ii | 2.903 (11) |
| | | |
C9—O2—C10 | 117.7 (4) | C7—C8—C9 | 115.2 (5) |
O1—C1—C6 | 117.3 (7) | C8—C9—C17 | 109.1 (6) |
O1—C1—C2 | 122.0 (8) | C16—C9—C17 | 110.2 (6) |
C2—C1—C6 | 120.7 (6) | O2—C9—C17 | 104.9 (5) |
C1—C2—C3 | 119.8 (8) | O2—C9—C8 | 108.8 (5) |
C2—C3—C4 | 122.1 (6) | O2—C9—C16 | 108.1 (6) |
C5—C4—C7 | 123.6 (6) | C8—C9—C16 | 115.2 (4) |
C3—C4—C5 | 116.0 (5) | O2—C10—C11 | 124.7 (6) |
C3—C4—C7 | 120.5 (6) | O2—C10—C15 | 114.4 (5) |
C4—C5—C6 | 122.2 (6) | C11—C10—C15 | 120.9 (6) |
C1—C6—C5 | 119.3 (6) | C7—C11—C12 | 121.8 (5) |
C8—C7—C18 | 107.1 (5) | C10—C11—C12 | 116.7 (6) |
C11—C7—C18 | 109.5 (6) | C7—C11—C10 | 121.4 (5) |
C8—C7—C11 | 108.3 (4) | C11—C12—C13 | 123.4 (5) |
C4—C7—C18 | 109.1 (4) | C12—C13—C14 | 119.1 (7) |
C4—C7—C8 | 111.2 (5) | C13—C14—C15 | 119.3 (8) |
C4—C7—C11 | 111.5 (5) | C10—C15—C14 | 120.6 (6) |
| | | |
C10—O2—C9—C8 | 41.6 (7) | C4—C7—C11—C10 | 108.5 (6) |
C10—O2—C9—C16 | −84.2 (7) | C4—C7—C11—C12 | −74.7 (8) |
C10—O2—C9—C17 | 158.2 (7) | C8—C7—C11—C10 | −14.1 (8) |
C9—O2—C10—C11 | −15.1 (10) | C8—C7—C11—C12 | 162.6 (6) |
C9—O2—C10—C15 | 166.8 (6) | C18—C7—C11—C10 | −130.6 (6) |
O1—C1—C2—C3 | −178.8 (6) | C11—C7—C8—C9 | 42.8 (7) |
C2—C1—C6—C5 | −0.8 (9) | C18—C7—C8—C9 | 160.9 (5) |
C6—C1—C2—C3 | 0.8 (10) | C18—C7—C11—C12 | 46.2 (7) |
O1—C1—C6—C5 | 178.8 (6) | C7—C8—C9—C17 | −171.3 (6) |
C1—C2—C3—C4 | 0.1 (10) | C7—C8—C9—C16 | 64.2 (8) |
C2—C3—C4—C5 | −0.9 (9) | C7—C8—C9—O2 | −57.3 (6) |
C2—C3—C4—C7 | 179.0 (6) | O2—C10—C11—C7 | 0.3 (10) |
C3—C4—C5—C6 | 0.9 (9) | C15—C10—C11—C12 | 1.4 (10) |
C3—C4—C7—C11 | −179.9 (5) | O2—C10—C11—C12 | −176.6 (6) |
C3—C4—C7—C18 | 59.0 (7) | C15—C10—C11—C7 | 178.3 (7) |
C5—C4—C7—C8 | 121.0 (6) | C11—C10—C15—C14 | 0.0 (12) |
C5—C4—C7—C11 | 0.0 (8) | O2—C10—C15—C14 | 178.2 (8) |
C5—C4—C7—C18 | −121.2 (6) | C10—C11—C12—C13 | −2.3 (10) |
C3—C4—C7—C8 | −58.9 (7) | C7—C11—C12—C13 | −179.2 (7) |
C7—C4—C5—C6 | −179.0 (5) | C11—C12—C13—C14 | 1.8 (12) |
C4—C5—C6—C1 | −0.1 (9) | C12—C13—C14—C15 | −0.3 (13) |
C4—C7—C8—C9 | −80.0 (7) | C13—C14—C15—C10 | −0.6 (13) |
Symmetry codes: (i) x−y, 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 m−3 |
Mr = 1683.1 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.24 (2) Å | θ = 5–22.5° |
c = 10.96 (1) Å | µ = 0.08 mm−1 |
V = 7043 (10) Å3 | T = 293 K |
Z = 3 | Acicular, hexagonal prism, colourless |
F(000) = 2712 | 0.5 × 0.15 × 0.15 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.056 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ' fixed, where the angle θ' is the projection
of θ on the equatorial plane. | k = −26→26 |
4108 measured reflections | l = 0→11 |
1555 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.061 | See text |
wR(F2) = 0.092 | w = 1/[σ2(F) + 0.00015F2] |
S = 1.23 | (Δ/σ)max = 0.001 |
1211 reflections | Δρmax = 0.33 e Å−3 |
215 parameters | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1194 (2) | 0.0557 (4) | 0.0183 (3) | 0.0607 (16) | |
O2 | 0.26100 (10) | 0.1745 (2) | 0.6256 (3) | 0.0516 (11) | |
C1 | 0.1610 (2) | 0.0732 (4) | 0.1092 (4) | 0.0432 (19) | |
C2 | 0.1747 (2) | 0.0356 (4) | 0.1639 (4) | 0.045 (2) | |
C3 | 0.2153 (2) | 0.0542 (4) | 0.2561 (4) | 0.0430 (19) | |
C4 | 0.2432 (2) | 0.1109 (4) | 0.2958 (3) | 0.0360 (16) | |
C5 | 0.2293 (2) | 0.1478 (4) | 0.2364 (4) | 0.041 (2) | |
C6 | 0.1884 (2) | 0.1296 (4) | 0.1444 (4) | 0.0432 (19) | |
C7 | 0.2869 (2) | 0.1294 (4) | 0.4008 (3) | 0.0362 (16) | |
C8 | 0.2599 (2) | 0.0952 (4) | 0.5191 (3) | 0.0386 (16) | |
C9 | 0.2247 (2) | 0.1140 (4) | 0.5935 (4) | 0.0417 (17) | |
C10 | 0.2982 (2) | 0.2108 (4) | 0.5380 (4) | 0.0408 (17) | |
C11 | 0.3125 (2) | 0.1927 (4) | 0.4313 (4) | 0.0384 (16) | |
C12 | 0.3527 (2) | 0.2349 (4) | 0.3551 (4) | 0.047 (2) | |
C13 | 0.3767 (2) | 0.2924 (4) | 0.3816 (4) | 0.052 (2) | |
C14 | 0.3612 (2) | 0.3090 (4) | 0.4875 (5) | 0.052 (2) | |
C15 | 0.3224 (2) | 0.2685 (4) | 0.5666 (4) | 0.0492 (19) | |
C16 | 0.1721 (2) | 0.1078 (4) | 0.5292 (4) | 0.054 (2) | |
C17 | 0.2092 (2) | 0.0832 (4) | 0.7162 (4) | 0.056 (2) | |
C18 | 0.3350 (2) | 0.1175 (4) | 0.3637 (4) | 0.0494 (19) | |
O3 | −0.00970 | 0.00000 | 0.16760 | 0.2249* | 0.167 |
O4 | 0.06100 | 0.05120 | 0.29430 | 0.2774* | 0.167 |
C20 | 0.00810 | 0.01900 | 0.27480 | 0.2012* | 0.167 |
C21 | −0.02890 | −0.01180 | 0.38610 | 0.2510* | 0.167 |
C22 | 0.00770 | 0.00950 | 0.50180 | 0.1605* | 0.167 |
H1 | 0.105 (4) | 0.019 (8) | 0.011 (7) | 0.17 (4)* | |
H2 | 0.1538 (2) | −0.0081 (4) | 0.1349 (4) | 0.044 (12)* | |
H3 | 0.2255 (2) | 0.0245 (4) | 0.2978 (4) | 0.075 (16)* | |
H4 | 0.2509 (2) | 0.1919 (4) | 0.2627 (4) | 0.062 (14)* | |
H5 | 0.1783 (2) | 0.1591 (4) | 0.1012 (4) | 0.070 (15)* | |
H6 | 0.2326 (2) | 0.0514 (4) | 0.4938 (3) | 0.058 (14)* | |
H7 | 0.2936 (2) | 0.0986 (4) | 0.5767 (3) | 0.041 (12)* | |
H8 | 0.3655 (2) | 0.2225 (4) | 0.2729 (4) | 0.069 (14)* | |
H9 | 0.4072 (2) | 0.3239 (4) | 0.3201 (4) | 0.067 (14)* | |
H10 | 0.3793 (2) | 0.3534 (4) | 0.5084 (5) | 0.072 (15)* | |
H11 | 0.3108 (2) | 0.2813 (4) | 0.6499 (4) | 0.059 (13)* | |
H12 | 0.1446 (2) | 0.0640 (4) | 0.5044 (4) | 0.092 (19)* | |
H13 | 0.1498 (2) | 0.1212 (4) | 0.5898 (4) | 0.082 (16)* | |
H14 | 0.1847 (2) | 0.1337 (4) | 0.4480 (4) | 0.13 (2)* | |
H15 | 0.1824 (2) | 0.0382 (4) | 0.7011 (4) | 0.082 (18)* | |
H16 | 0.2473 (2) | 0.0909 (4) | 0.7627 (4) | 0.11 (2)* | |
H17 | 0.1868 (2) | 0.0985 (4) | 0.7713 (4) | 0.090 (18)* | |
H18 | 0.3552 (2) | 0.1406 (4) | 0.2814 (4) | 0.067 (15)* | |
H19 | 0.3660 (2) | 0.1310 (4) | 0.4362 (4) | 0.070 (15)* | |
H20 | 0.3173 (2) | 0.0726 (4) | 0.3478 (4) | 0.068 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.060 (3) | 0.061 (3) | 0.058 (2) | 0.028 (3) | −0.018 (2) | −0.011 (2) |
O2 | 0.053 (2) | 0.042 (2) | 0.0560 (18) | 0.021 (2) | 0.0064 (17) | −0.0096 (18) |
C1 | 0.039 (4) | 0.044 (3) | 0.039 (3) | 0.015 (3) | −0.004 (3) | −0.005 (3) |
C2 | 0.055 (4) | 0.030 (4) | 0.045 (3) | 0.017 (3) | −0.003 (3) | −0.004 (3) |
C3 | 0.047 (3) | 0.037 (4) | 0.045 (3) | 0.021 (3) | −0.004 (3) | −0.004 (3) |
C4 | 0.039 (3) | 0.032 (3) | 0.036 (2) | 0.017 (3) | 0.006 (2) | 0.000 (2) |
C5 | 0.047 (4) | 0.029 (4) | 0.042 (2) | 0.016 (3) | −0.001 (3) | 0.000 (3) |
C6 | 0.049 (3) | 0.039 (4) | 0.047 (3) | 0.026 (3) | −0.006 (3) | −0.004 (3) |
C7 | 0.038 (3) | 0.034 (3) | 0.042 (2) | 0.022 (3) | −0.002 (2) | −0.002 (2) |
C8 | 0.043 (3) | 0.038 (3) | 0.041 (2) | 0.025 (3) | −0.002 (2) | 0.002 (2) |
C9 | 0.044 (3) | 0.034 (3) | 0.045 (3) | 0.018 (3) | 0.005 (3) | −0.001 (3) |
C10 | 0.033 (3) | 0.038 (3) | 0.049 (3) | 0.016 (3) | 0.000 (3) | 0.005 (3) |
C11 | 0.036 (3) | 0.038 (3) | 0.042 (2) | 0.019 (3) | −0.006 (2) | −0.005 (3) |
C12 | 0.046 (4) | 0.040 (4) | 0.050 (3) | 0.017 (3) | −0.001 (3) | 0.005 (3) |
C13 | 0.052 (4) | 0.038 (4) | 0.055 (3) | 0.015 (3) | −0.005 (3) | 0.005 (3) |
C14 | 0.044 (4) | 0.035 (4) | 0.072 (3) | 0.016 (3) | −0.017 (3) | −0.004 (3) |
C15 | 0.048 (3) | 0.034 (4) | 0.065 (3) | 0.020 (3) | −0.010 (3) | −0.013 (3) |
C16 | 0.041 (4) | 0.063 (4) | 0.066 (3) | 0.031 (3) | −0.001 (3) | −0.011 (3) |
C17 | 0.065 (4) | 0.061 (4) | 0.048 (3) | 0.035 (4) | 0.013 (3) | 0.010 (3) |
C18 | 0.049 (3) | 0.048 (4) | 0.063 (3) | 0.033 (3) | 0.002 (3) | −0.001 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.401 (8) | C7—C11 | 1.539 (10) |
O2—C9 | 1.479 (8) | C7—C18 | 1.553 (10) |
O2—C10 | 1.387 (7) | C8—C9 | 1.529 (9) |
C1—C2 | 1.389 (9) | C9—C17 | 1.529 (7) |
C1—C6 | 1.385 (10) | C9—C16 | 1.528 (9) |
C2—C3 | 1.393 (8) | C10—C15 | 1.403 (10) |
C3—C4 | 1.407 (10) | C10—C11 | 1.398 (8) |
C4—C5 | 1.399 (9) | C11—C12 | 1.400 (9) |
C4—C7 | 1.548 (7) | C12—C13 | 1.393 (10) |
C5—C6 | 1.397 (8) | C13—C14 | 1.386 (8) |
C7—C8 | 1.551 (7) | C14—C15 | 1.386 (9) |
| | | |
O1···O1i | 2.847 (11) | O1···O1ii | 2.847 (12) |
| | | |
C9—O2—C10 | 118.2 (4) | C7—C8—C9 | 115.7 (5) |
O1—C1—C6 | 118.1 (6) | C16—C9—C17 | 111.0 (5) |
C2—C1—C6 | 120.2 (5) | O2—C9—C16 | 107.5 (5) |
O1—C1—C2 | 121.7 (6) | O2—C9—C17 | 104.5 (4) |
C1—C2—C3 | 120.1 (6) | C8—C9—C17 | 109.4 (5) |
C2—C3—C4 | 121.2 (6) | O2—C9—C8 | 108.6 (5) |
C5—C4—C7 | 123.5 (6) | C8—C9—C16 | 115.3 (4) |
C3—C4—C7 | 119.5 (6) | O2—C10—C11 | 124.1 (6) |
C3—C4—C5 | 116.9 (5) | C11—C10—C15 | 121.6 (6) |
C4—C5—C6 | 122.4 (6) | O2—C10—C15 | 114.2 (4) |
C1—C6—C5 | 119.1 (6) | C7—C11—C10 | 121.8 (5) |
C8—C7—C18 | 106.8 (5) | C10—C11—C12 | 116.8 (6) |
C11—C7—C18 | 109.5 (6) | C7—C11—C12 | 121.4 (5) |
C8—C7—C11 | 107.7 (4) | C11—C12—C13 | 122.2 (5) |
C4—C7—C8 | 111.7 (5) | C12—C13—C14 | 119.5 (6) |
C4—C7—C11 | 111.7 (5) | C13—C14—C15 | 120.0 (6) |
C4—C7—C18 | 109.2 (4) | C10—C15—C14 | 119.8 (5) |
| | | |
C10—O2—C9—C8 | 40.2 (6) | C4—C7—C11—C10 | 107.5 (6) |
C10—O2—C9—C16 | −85.1 (5) | C4—C7—C11—C12 | −74.6 (7) |
C10—O2—C9—C17 | 156.9 (5) | C8—C7—C11—C10 | −15.5 (8) |
C9—O2—C10—C11 | −14.0 (8) | C8—C7—C11—C12 | 162.4 (6) |
C9—O2—C10—C15 | 167.8 (5) | C18—C7—C11—C10 | −131.4 (6) |
O1—C1—C2—C3 | −178.4 (5) | C11—C7—C8—C9 | 44.3 (7) |
C2—C1—C6—C5 | −0.8 (9) | C18—C7—C8—C9 | 161.9 (5) |
C6—C1—C2—C3 | 1.2 (9) | C18—C7—C11—C12 | 46.5 (7) |
O1—C1—C6—C5 | 178.9 (5) | C7—C8—C9—C17 | −170.8 (5) |
C1—C2—C3—C4 | 0.0 (9) | C7—C8—C9—C16 | 63.2 (8) |
C2—C3—C4—C5 | −1.6 (8) | C7—C8—C9—O2 | −57.4 (6) |
C2—C3—C4—C7 | 178.4 (5) | O2—C10—C11—C7 | 0.8 (10) |
C3—C4—C5—C6 | 2.0 (8) | C15—C10—C11—C12 | 0.8 (9) |
C3—C4—C7—C11 | −179.7 (5) | O2—C10—C11—C12 | −177.2 (5) |
C3—C4—C7—C18 | 59.0 (7) | C15—C10—C11—C7 | 178.8 (6) |
C5—C4—C7—C8 | 121.0 (6) | C11—C10—C15—C14 | 0.5 (10) |
C5—C4—C7—C11 | 0.3 (7) | O2—C10—C15—C14 | 178.6 (5) |
C5—C4—C7—C18 | −121.0 (6) | C10—C11—C12—C13 | −1.5 (9) |
C3—C4—C7—C8 | −59.0 (7) | C7—C11—C12—C13 | −179.5 (6) |
C7—C4—C5—C6 | −178.0 (5) | C11—C12—C13—C14 | 0.9 (10) |
C4—C5—C6—C1 | −0.9 (9) | C12—C13—C14—C15 | 0.5 (10) |
C4—C7—C8—C9 | −78.7 (7) | C13—C14—C15—C10 | −1.1 (10) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 0.88 (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 m−3 |
Mr = 1698.3 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.26 (2) Å | θ = 5–25° |
c = 11.00 (1) Å | µ = 0.08 mm−1 |
V = 7079 (10) Å3 | T = 293 K |
Z = 3 | Acicular, hexagonal prism, colourless |
F(000) = 2736 | 0.6 × 0.20 × 0.20 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.018 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ'fixed, where the angle θ' is the projection
of θ on the equatorial plane | k = −26→26 |
4683 measured reflections | l = 0→11 |
1659 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.053 | See text |
wR(F2) = 0.052 | w = 1/[σ2(F) + 0.000097) |
S = 1.08 | (Δ/σ)max = 0.001 |
1376 reflections | Δρmax = 0.27 e Å−3 |
215 parameters | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.11800 (10) | 0.0558 (2) | 0.0206 (2) | 0.0606 (11) | |
O2 | 0.26160 (10) | 0.1749 (2) | 0.6271 (2) | 0.0527 (10) | |
C1 | 0.1601 (2) | 0.0734 (4) | 0.1102 (3) | 0.0429 (15) | |
C2 | 0.1741 (2) | 0.0361 (4) | 0.1644 (3) | 0.0481 (15) | |
C3 | 0.2148 (2) | 0.0546 (4) | 0.2558 (3) | 0.0443 (15) | |
C4 | 0.24340 (10) | 0.1113 (2) | 0.2953 (3) | 0.0381 (11) | |
C5 | 0.22910 (10) | 0.1481 (3) | 0.2366 (3) | 0.0429 (15) | |
C6 | 0.1879 (2) | 0.1296 (4) | 0.1446 (3) | 0.0446 (15) | |
C7 | 0.28720 (10) | 0.1300 (2) | 0.4010 (3) | 0.0365 (11) | |
C8 | 0.26050 (10) | 0.0962 (2) | 0.5195 (3) | 0.0401 (11) | |
C9 | 0.2258 (2) | 0.1150 (4) | 0.5950 (3) | 0.0442 (11) | |
C10 | 0.29810 (10) | 0.2107 (2) | 0.5388 (3) | 0.0418 (11) | |
C11 | 0.31270 (10) | 0.1930 (2) | 0.4309 (3) | 0.0391 (11) | |
C12 | 0.3526 (2) | 0.2351 (4) | 0.3542 (3) | 0.0478 (15) | |
C13 | 0.3767 (2) | 0.2925 (4) | 0.3805 (3) | 0.0534 (16) | |
C14 | 0.3613 (2) | 0.3089 (4) | 0.4873 (3) | 0.0554 (17) | |
C15 | 0.3224 (2) | 0.2683 (4) | 0.5667 (3) | 0.0513 (16) | |
C16 | 0.1732 (2) | 0.1085 (4) | 0.5300 (3) | 0.0553 (16) | |
C17 | 0.2098 (2) | 0.0840 (4) | 0.7179 (3) | 0.0590 (16) | |
C18 | 0.3349 (2) | 0.1180 (4) | 0.3628 (3) | 0.0512 (16) | |
O3 | 0.00800 | −0.02020 | 0.21080 | 0.2575* | 0.167 |
O4 | 0.05010 | 0.05980 | 0.31580 | 0.3214* | 0.167 |
C20 | 0.01190 | 0.00770 | 0.30740 | 0.1864* | 0.167 |
C21 | −0.02140 | −0.02360 | 0.42220 | 0.0936* | 0.167 |
C22 | 0.00520 | 0.01510 | 0.53380 | 0.1029* | 0.167 |
C23 | −0.02670 | −0.01750 | 0.64900 | 0.1398* | 0.167 |
H1 | 0.103 (2) | 0.021 (5) | 0.015 (5) | 0.14 (3)* | |
H2 | 0.1532 (2) | −0.0077 (4) | 0.1356 (3) | 0.065 (11)* | |
H3 | 0.2248 (2) | 0.0248 (4) | 0.2974 (3) | 0.058 (10)* | |
H4 | 0.25040 (10) | 0.1920 (3) | 0.2630 (3) | 0.065 (11)* | |
H5 | 0.1781 (2) | 0.1592 (4) | 0.1011 (3) | 0.063 (11)* | |
H6 | 0.23300 (10) | 0.0524 (2) | 0.4946 (3) | 0.055 (10)* | |
H7 | 0.29440 (10) | 0.0996 (2) | 0.5761 (3) | 0.051 (9)* | |
H8 | 0.3651 (2) | 0.2227 (4) | 0.2719 (3) | 0.055 (9)* | |
H9 | 0.4070 (2) | 0.3240 (4) | 0.3190 (3) | 0.061 (10)* | |
H10 | 0.3796 (2) | 0.3533 (4) | 0.5085 (3) | 0.063 (10)* | |
H11 | 0.3110 (2) | 0.2813 (4) | 0.6497 (3) | 0.053 (9)* | |
H12 | 0.1460 (2) | 0.0648 (4) | 0.5052 (3) | 0.114 (17)* | |
H13 | 0.1507 (2) | 0.1219 (4) | 0.5899 (3) | 0.087 (13)* | |
H14 | 0.1860 (2) | 0.1345 (4) | 0.4491 (3) | 0.114 (16)* | |
H15 | 0.1831 (2) | 0.0391 (4) | 0.7027 (3) | 0.101 (16)* | |
H16 | 0.2478 (2) | 0.0918 (4) | 0.7650 (3) | 0.085 (14)* | |
H17 | 0.1872 (2) | 0.0992 (4) | 0.7723 (3) | 0.089 (13)* | |
H18 | 0.3546 (2) | 0.1409 (4) | 0.2804 (3) | 0.059 (10)* | |
H19 | 0.3662 (2) | 0.1316 (4) | 0.4342 (3) | 0.066 (11)* | |
H20 | 0.3171 (2) | 0.0732 (4) | 0.3472 (3) | 0.084 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.054 (2) | 0.056 (2) | 0.0658 (16) | 0.0230 (18) | −0.0184 (15) | −0.0104 (15) |
O2 | 0.0498 (18) | 0.0403 (18) | 0.0638 (14) | 0.0193 (16) | 0.0073 (13) | −0.0078 (13) |
C1 | 0.039 (3) | 0.040 (3) | 0.0460 (18) | 0.017 (2) | −0.0035 (19) | −0.0022 (19) |
C2 | 0.054 (3) | 0.033 (3) | 0.0522 (19) | 0.018 (2) | −0.002 (2) | −0.004 (2) |
C3 | 0.052 (3) | 0.034 (3) | 0.0477 (18) | 0.022 (2) | −0.0034 (18) | 0.0011 (19) |
C4 | 0.040 (2) | 0.031 (2) | 0.0450 (17) | 0.019 (2) | 0.0053 (18) | 0.0018 (18) |
C5 | 0.044 (3) | 0.035 (3) | 0.0488 (18) | 0.019 (2) | −0.0028 (19) | −0.0029 (19) |
C6 | 0.047 (3) | 0.038 (3) | 0.0512 (19) | 0.023 (2) | −0.0008 (19) | 0.0013 (19) |
C7 | 0.030 (2) | 0.033 (2) | 0.0487 (17) | 0.0173 (19) | 0.0013 (17) | 0.0009 (17) |
C8 | 0.039 (2) | 0.037 (2) | 0.0496 (17) | 0.023 (2) | −0.0019 (18) | −0.0005 (18) |
C9 | 0.040 (2) | 0.035 (2) | 0.0553 (19) | 0.017 (2) | −0.0003 (19) | −0.0001 (19) |
C10 | 0.034 (2) | 0.036 (2) | 0.0560 (19) | 0.018 (2) | −0.0023 (19) | 0.0031 (19) |
C11 | 0.034 (2) | 0.037 (2) | 0.0465 (18) | 0.018 (2) | −0.0059 (18) | −0.0007 (18) |
C12 | 0.040 (3) | 0.040 (3) | 0.0540 (19) | 0.013 (2) | −0.0014 (19) | 0.005 (2) |
C13 | 0.047 (3) | 0.035 (3) | 0.067 (2) | 0.012 (3) | −0.007 (2) | 0.007 (2) |
C14 | 0.048 (3) | 0.034 (3) | 0.081 (3) | 0.018 (2) | −0.018 (2) | −0.005 (2) |
C15 | 0.048 (3) | 0.039 (3) | 0.070 (2) | 0.024 (2) | −0.011 (2) | −0.012 (2) |
C16 | 0.040 (3) | 0.061 (3) | 0.070 (2) | 0.029 (2) | 0.001 (2) | −0.004 (2) |
C17 | 0.066 (3) | 0.064 (3) | 0.053 (2) | 0.037 (3) | 0.013 (2) | 0.013 (2) |
C18 | 0.043 (3) | 0.049 (3) | 0.067 (2) | 0.027 (2) | 0.004 (2) | −0.002 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.403 (6) | C7—C11 | 1.532 (5) |
O2—C9 | 1.466 (8) | C7—C18 | 1.549 (8) |
O2—C10 | 1.384 (5) | C8—C9 | 1.527 (7) |
C1—C6 | 1.380 (10) | C9—C17 | 1.537 (6) |
C1—C2 | 1.387 (9) | C9—C16 | 1.531 (9) |
C2—C3 | 1.392 (8) | C10—C11 | 1.411 (5) |
C3—C4 | 1.407 (8) | C10—C15 | 1.399 (8) |
C4—C7 | 1.558 (5) | C11—C12 | 1.401 (7) |
C4—C5 | 1.402 (5) | C12—C13 | 1.391 (10) |
C5—C6 | 1.405 (7) | C13—C14 | 1.394 (7) |
C7—C8 | 1.552 (5) | C14—C15 | 1.392 (8) |
| | | |
O1···O1i | 2.824 (6) | O1···O1ii | 2.824 (6) |
| | | |
C9—O2—C10 | 117.4 (3) | C7—C8—C9 | 116.3 (3) |
C2—C1—C6 | 119.8 (5) | O2—C9—C8 | 109.0 (5) |
O1—C1—C6 | 118.3 (5) | O2—C9—C17 | 104.4 (4) |
O1—C1—C2 | 122.0 (6) | C8—C9—C16 | 114.1 (3) |
C1—C2—C3 | 120.4 (6) | C8—C9—C17 | 110.3 (5) |
C2—C3—C4 | 121.6 (6) | C16—C9—C17 | 110.8 (5) |
C5—C4—C7 | 123.4 (3) | O2—C9—C16 | 107.7 (5) |
C3—C4—C7 | 120.2 (3) | C11—C10—C15 | 120.8 (3) |
C3—C4—C5 | 116.4 (4) | O2—C10—C11 | 125.1 (3) |
C4—C5—C6 | 122.2 (5) | O2—C10—C15 | 114.0 (3) |
C1—C6—C5 | 119.5 (5) | C7—C11—C10 | 121.1 (3) |
C8—C7—C18 | 107.3 (3) | C7—C11—C12 | 121.3 (4) |
C4—C7—C8 | 112.2 (3) | C10—C11—C12 | 117.5 (4) |
C4—C7—C11 | 111.8 (3) | C11—C12—C13 | 122.2 (4) |
C11—C7—C18 | 109.7 (4) | C12—C13—C14 | 119.2 (5) |
C8—C7—C11 | 107.5 (3) | C13—C14—C15 | 120.4 (6) |
C4—C7—C18 | 108.4 (3) | C10—C15—C14 | 120.0 (4) |
| | | |
C10—O2—C9—C8 | 40.1 (5) | C4—C7—C11—C10 | 108.1 (3) |
C10—O2—C9—C16 | −84.2 (5) | C4—C7—C11—C12 | −73.9 (5) |
C10—O2—C9—C17 | 157.9 (4) | C8—C7—C11—C10 | −15.4 (4) |
C9—O2—C10—C11 | −14.4 (6) | C8—C7—C11—C12 | 162.6 (4) |
C9—O2—C10—C15 | 168.0 (5) | C18—C7—C11—C10 | −131.7 (3) |
O1—C1—C2—C3 | −177.9 (5) | C11—C7—C8—C9 | 43.9 (4) |
C2—C1—C6—C5 | −1.7 (8) | C18—C7—C8—C9 | 161.8 (4) |
C6—C1—C2—C3 | 1.9 (8) | C18—C7—C11—C12 | 46.3 (5) |
O1—C1—C6—C5 | 178.2 (4) | C7—C8—C9—C17 | −171.4 (4) |
C1—C2—C3—C4 | −0.7 (8) | C7—C8—C9—C16 | 63.1 (6) |
C2—C3—C4—C5 | −0.7 (7) | C7—C8—C9—O2 | −57.4 (4) |
C2—C3—C4—C7 | 177.9 (4) | O2—C10—C11—C7 | 1.2 (5) |
C3—C4—C5—C6 | 1.0 (6) | C15—C10—C11—C12 | 0.6 (6) |
C3—C4—C7—C11 | −179.1 (4) | O2—C10—C11—C12 | −176.9 (4) |
C3—C4—C7—C18 | 59.9 (5) | C15—C10—C11—C7 | 178.7 (4) |
C5—C4—C7—C8 | 120.1 (4) | C11—C10—C15—C14 | 0.3 (7) |
C5—C4—C7—C11 | −0.7 (5) | O2—C10—C15—C14 | 178.0 (5) |
C5—C4—C7—C18 | −121.6 (4) | C10—C11—C12—C13 | −1.2 (7) |
C3—C4—C7—C8 | −58.3 (5) | C7—C11—C12—C13 | −179.3 (5) |
C7—C4—C5—C6 | −177.6 (4) | C11—C12—C13—C14 | 0.8 (9) |
C4—C5—C6—C1 | 0.2 (7) | C12—C13—C14—C15 | 0.2 (9) |
C4—C7—C8—C9 | −79.3 (4) | C13—C14—C15—C10 | −0.7 (9) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
(DIV) [4-
p-hydroxyphenyl-2,2,4-trimethylchroman]-valeric acid
top
Crystal data top
6(C18H20O2)·(C5H10O2) | Dx = 1.210 Mg m−3 |
Mr = 1712.3 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.21 (2) Å | θ = 5–25° |
c = 10.93 (1) Å | µ = 0.08 mm−1 |
V = 7008 (10) Å3 | T = 293 K |
Z = 3 | Acicular,hexagonal prism, colourless |
F(000) = 2760 | 0.6 × 0.2 × 0.2 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.084 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan2θ'fixed, where the angle θ' is the peojection
of θ on the equatorial plane. | k = −26→26 |
4214 measured reflections | l = 0→11 |
1535 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.070 | See text |
wR(F2) = 0.053 | w = 1/[σ2(F) + 0.000091F2] |
S = 1.55 | (Δ/σ)max = 0.001 |
1244 reflections | Δρmax = 0.40 e Å−3 |
215 parameters | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1190 (2) | 0.0567 (4) | 0.0190 (3) | 0.0576 (15) | |
O2 | 0.26170 (10) | 0.1749 (2) | 0.6271 (2) | 0.0508 (11) | |
C1 | 0.1606 (2) | 0.0735 (4) | 0.1097 (3) | 0.0411 (16) | |
C2 | 0.1745 (2) | 0.0364 (4) | 0.1636 (3) | 0.0441 (16) | |
C3 | 0.2151 (2) | 0.0548 (4) | 0.2556 (3) | 0.0431 (16) | |
C4 | 0.2435 (2) | 0.1114 (4) | 0.2956 (3) | 0.0357 (15) | |
C5 | 0.2294 (2) | 0.1483 (4) | 0.2363 (3) | 0.0399 (16) | |
C6 | 0.1883 (2) | 0.1299 (4) | 0.1440 (3) | 0.0420 (16) | |
C7 | 0.2872 (2) | 0.1301 (4) | 0.4008 (3) | 0.0342 (16) | |
C8 | 0.2604 (2) | 0.0960 (4) | 0.5192 (3) | 0.0369 (15) | |
C9 | 0.2255 (2) | 0.1151 (4) | 0.5950 (3) | 0.0427 (16) | |
C10 | 0.2983 (2) | 0.2109 (4) | 0.5388 (3) | 0.0400 (16) | |
C11 | 0.3125 (2) | 0.1928 (4) | 0.4313 (3) | 0.0361 (16) | |
C12 | 0.3524 (2) | 0.2347 (4) | 0.3543 (3) | 0.0446 (16) | |
C13 | 0.3767 (2) | 0.2921 (4) | 0.3801 (4) | 0.0520 (17) | |
C14 | 0.3614 (2) | 0.3089 (4) | 0.4863 (4) | 0.0534 (17) | |
C15 | 0.3227 (2) | 0.2686 (4) | 0.5669 (4) | 0.0506 (17) | |
C16 | 0.1732 (2) | 0.1089 (4) | 0.5298 (4) | 0.0523 (17) | |
C17 | 0.2093 (2) | 0.0838 (4) | 0.7177 (4) | 0.058 (2) | |
C18 | 0.3348 (2) | 0.1178 (4) | 0.3633 (3) | 0.0478 (17) | |
O3 | −0.00140 | −0.02200 | 0.17040 | 0.1700* | 0.167 |
O4 | 0.04080 | 0.05840 | 0.27400 | 0.1827* | 0.167 |
C20 | 0.00440 | 0.00560 | 0.26850 | 0.1175* | 0.167 |
C21 | −0.02380 | −0.02620 | 0.38680 | 0.1458* | 0.167 |
C22 | 0.00510 | 0.01320 | 0.49620 | 0.1047* | 0.167 |
C23 | −0.02150 | −0.01980 | 0.61450 | 0.0906* | 0.167 |
C24 | 0.00990 | 0.01790 | 0.72430 | 0.1945* | 0.167 |
H1 | 0.106 (2) | 0.023 (5) | 0.015 (5) | 0.10 (3)* | |
H2 | 0.1533 (2) | −0.0075 (4) | 0.1351 (3) | 0.067 (13)* | |
H3 | 0.2252 (2) | 0.0249 (4) | 0.2969 (3) | 0.069 (13)* | |
H4 | 0.2508 (2) | 0.1924 (4) | 0.2630 (3) | 0.059 (12)* | |
H5 | 0.1788 (2) | 0.1598 (4) | 0.1001 (3) | 0.061 (13)* | |
H6 | 0.2329 (2) | 0.0521 (4) | 0.4940 (3) | 0.043 (11)* | |
H7 | 0.2944 (2) | 0.0994 (4) | 0.5763 (3) | 0.043 (11)* | |
H8 | 0.3648 (2) | 0.2220 (4) | 0.2717 (3) | 0.051 (11)* | |
H9 | 0.4071 (2) | 0.3235 (4) | 0.3180 (4) | 0.070 (13)* | |
H10 | 0.3798 (2) | 0.3535 (4) | 0.5073 (4) | 0.066 (13)* | |
H11 | 0.3114 (2) | 0.2816 (4) | 0.6506 (4) | 0.055 (12)* | |
H12 | 0.1456 (2) | 0.0650 (4) | 0.5051 (4) | 0.11 (2)* | |
H13 | 0.1508 (2) | 0.1225 (4) | 0.5901 (4) | 0.080 (15)* | |
H14 | 0.1860 (2) | 0.1348 (4) | 0.4483 (4) | 0.12 (2)* | |
H15 | 0.1822 (2) | 0.0388 (4) | 0.7022 (4) | 0.084 (16)* | |
H16 | 0.2472 (2) | 0.0910 (4) | 0.7649 (4) | 0.092 (17)* | |
H17 | 0.1871 (2) | 0.0994 (4) | 0.7727 (4) | 0.100 (17)* | |
H18 | 0.3548 (2) | 0.1408 (4) | 0.2806 (3) | 0.088 (15)* | |
H19 | 0.3660 (2) | 0.1311 (4) | 0.4354 (3) | 0.060 (12)* | |
H20 | 0.3167 (2) | 0.0729 (4) | 0.3473 (3) | 0.066 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.059 (3) | 0.055 (3) | 0.0542 (19) | 0.025 (2) | −0.0145 (18) | −0.0078 (18) |
O2 | 0.049 (2) | 0.042 (2) | 0.0552 (16) | 0.0182 (19) | 0.0077 (15) | −0.0066 (16) |
C1 | 0.040 (3) | 0.045 (3) | 0.034 (2) | 0.018 (3) | −0.004 (2) | −0.001 (2) |
C2 | 0.054 (3) | 0.033 (3) | 0.043 (2) | 0.020 (3) | −0.003 (3) | −0.001 (3) |
C3 | 0.050 (3) | 0.037 (3) | 0.044 (2) | 0.023 (3) | −0.004 (2) | −0.001 (2) |
C4 | 0.038 (3) | 0.033 (3) | 0.0350 (19) | 0.017 (3) | 0.004 (2) | 0.001 (2) |
C5 | 0.042 (3) | 0.030 (3) | 0.045 (2) | 0.016 (3) | −0.003 (2) | −0.002 (2) |
C6 | 0.048 (3) | 0.036 (3) | 0.042 (2) | 0.021 (3) | 0.000 (2) | 0.003 (2) |
C7 | 0.032 (3) | 0.031 (3) | 0.040 (2) | 0.016 (2) | 0.001 (2) | 0.002 (2) |
C8 | 0.041 (3) | 0.035 (3) | 0.0388 (19) | 0.022 (3) | −0.004 (2) | −0.001 (2) |
C9 | 0.041 (3) | 0.035 (3) | 0.048 (2) | 0.016 (3) | 0.000 (2) | 0.001 (2) |
C10 | 0.035 (3) | 0.038 (3) | 0.048 (2) | 0.019 (3) | 0.001 (2) | 0.004 (2) |
C11 | 0.034 (3) | 0.035 (3) | 0.039 (2) | 0.017 (2) | −0.005 (2) | 0.000 (2) |
C12 | 0.042 (3) | 0.039 (3) | 0.043 (2) | 0.013 (3) | −0.005 (2) | −0.001 (2) |
C13 | 0.051 (3) | 0.043 (3) | 0.056 (3) | 0.019 (3) | −0.008 (3) | 0.003 (3) |
C14 | 0.048 (3) | 0.033 (3) | 0.075 (3) | 0.017 (3) | −0.018 (3) | −0.002 (3) |
C15 | 0.050 (3) | 0.041 (3) | 0.065 (3) | 0.026 (3) | −0.011 (3) | −0.009 (3) |
C16 | 0.041 (3) | 0.062 (3) | 0.057 (3) | 0.028 (3) | 0.000 (3) | −0.007 (3) |
C17 | 0.067 (4) | 0.060 (4) | 0.049 (2) | 0.033 (3) | 0.014 (3) | 0.014 (3) |
C18 | 0.044 (3) | 0.049 (3) | 0.054 (3) | 0.026 (3) | 0.002 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.398 (8) | C7—C8 | 1.546 (7) |
O2—C9 | 1.462 (8) | C7—C18 | 1.546 (9) |
O2—C10 | 1.381 (6) | C8—C9 | 1.534 (9) |
C1—C2 | 1.375 (9) | C9—C16 | 1.524 (9) |
C1—C6 | 1.381 (10) | C9—C17 | 1.531 (7) |
C2—C3 | 1.389 (8) | C10—C15 | 1.399 (10) |
C3—C4 | 1.404 (10) | C10—C11 | 1.401 (7) |
C4—C5 | 1.400 (9) | C11—C12 | 1.396 (9) |
C4—C7 | 1.546 (7) | C12—C13 | 1.387 (10) |
C5—C6 | 1.400 (8) | C13—C14 | 1.386 (8) |
C7—C11 | 1.524 (10) | C14—C15 | 1.390 (9) |
| | | |
O1···O1i | 2.836 (11) | O1···O1ii | 2.836 (12) |
| | | |
C9—O2—C10 | 117.9 (3) | C7—C8—C9 | 115.8 (5) |
O1—C1—C2 | 122.6 (6) | O2—C9—C17 | 104.8 (4) |
C2—C1—C6 | 120.1 (5) | O2—C9—C8 | 108.7 (5) |
O1—C1—C6 | 117.3 (6) | C8—C9—C17 | 109.9 (5) |
C1—C2—C3 | 120.4 (6) | C16—C9—C17 | 110.8 (5) |
C2—C3—C4 | 121.6 (6) | O2—C9—C16 | 107.9 (5) |
C3—C4—C5 | 116.4 (5) | C8—C9—C16 | 114.3 (4) |
C3—C4—C7 | 120.2 (6) | C11—C10—C15 | 121.3 (5) |
C5—C4—C7 | 123.3 (6) | O2—C10—C11 | 124.4 (6) |
C4—C5—C6 | 122.2 (6) | O2—C10—C15 | 114.3 (4) |
C1—C6—C5 | 119.2 (6) | C10—C11—C12 | 117.2 (6) |
C4—C7—C18 | 108.7 (4) | C7—C11—C12 | 120.9 (4) |
C8—C7—C11 | 107.6 (4) | C7—C11—C10 | 121.8 (5) |
C8—C7—C18 | 106.7 (5) | C11—C12—C13 | 122.4 (5) |
C11—C7—C18 | 110.0 (6) | C12—C13—C14 | 119.3 (6) |
C4—C7—C8 | 111.8 (5) | C13—C14—C15 | 120.3 (6) |
C4—C7—C11 | 112.0 (5) | C10—C15—C14 | 119.6 (5) |
| | | |
C10—O2—C9—C8 | 40.6 (6) | C4—C7—C11—C10 | 107.8 (6) |
C10—O2—C9—C16 | −83.9 (5) | C4—C7—C11—C12 | −74.3 (7) |
C10—O2—C9—C17 | 158.0 (5) | C8—C7—C11—C10 | −15.4 (8) |
C9—O2—C10—C11 | −14.8 (8) | C8—C7—C11—C12 | 162.6 (6) |
C9—O2—C10—C15 | 167.5 (5) | C18—C7—C11—C10 | −131.2 (6) |
O1—C1—C2—C3 | −178.3 (5) | C11—C7—C8—C9 | 43.8 (7) |
C2—C1—C6—C5 | −1.7 (8) | C18—C7—C8—C9 | 161.8 (5) |
C6—C1—C2—C3 | 2.1 (8) | C18—C7—C11—C12 | 46.7 (6) |
O1—C1—C6—C5 | 178.7 (5) | C7—C8—C9—C17 | −171.5 (5) |
C1—C2—C3—C4 | −0.6 (8) | C7—C8—C9—C16 | 63.2 (8) |
C2—C3—C4—C5 | −1.1 (8) | C7—C8—C9—O2 | −57.4 (6) |
C2—C3—C4—C7 | 178.2 (5) | O2—C10—C11—C7 | 1.2 (9) |
C3—C4—C5—C6 | 1.5 (8) | C15—C10—C11—C12 | 0.7 (9) |
C3—C4—C7—C11 | −179.2 (5) | O2—C10—C11—C12 | −176.9 (5) |
C3—C4—C7—C18 | 59.1 (7) | C15—C10—C11—C7 | 178.7 (6) |
C5—C4—C7—C8 | 120.9 (6) | C11—C10—C15—C14 | 0.6 (9) |
C5—C4—C7—C11 | 0.1 (7) | O2—C10—C15—C14 | 178.4 (5) |
C5—C4—C7—C18 | −121.7 (6) | C10—C11—C12—C13 | −1.2 (9) |
C3—C4—C7—C8 | −58.4 (7) | C7—C11—C12—C13 | −179.3 (6) |
C7—C4—C5—C6 | −177.8 (5) | C11—C12—C13—C14 | 0.4 (10) |
C4—C5—C6—C1 | −0.1 (8) | C12—C13—C14—C15 | 0.9 (10) |
C4—C7—C8—C9 | −79.5 (7) | C13—C14—C15—C10 | −1.4 (9) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
(DII) [4-
p-hydroxyphenyl-2,2,4-trimethylchroman]-isobutyric acid
top
Crystal data top
6(C18H20O2)·(C4H8O2) | Dx = 1.204 Mg m−3 |
Mr = 1698.3 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.13 (2) Å | θ = 5–25.0° |
c = 10.97 (1) Å | µ = 0.08 mm−1 |
V = 6993 (10) Å3 | T = 293 K |
Z = 3 | Acicular, hexagonal prism, colourless |
F(000) = 2736 | 0.80 × 0.25 × 0.25 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.075 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ'fixed, where θ' is the projection
of θ on the equatorial plane | k = −26→26 |
4376 measured reflections | l = 0→11 |
1594 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.066 | See text |
wR(F2) = 0.057 | w = 1/[σ2(F) + 0.001F2] |
S = 1.23 | (Δ/σ)max = 0.002 |
1353 reflections | Δρmax = 0.68 e Å−3 |
215 parameters | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.11920 (10) | 0.0550 (3) | 0.0199 (3) | 0.0636 (13) | |
O2 | 0.26190 (10) | 0.1748 (2) | 0.6260 (2) | 0.0525 (11) | |
C1 | 0.1610 (2) | 0.0731 (4) | 0.1095 (3) | 0.0465 (16) | |
C2 | 0.1750 (2) | 0.0359 (4) | 0.1646 (4) | 0.0482 (16) | |
C3 | 0.2156 (2) | 0.0547 (4) | 0.2557 (4) | 0.0455 (16) | |
C4 | 0.2434 (2) | 0.1111 (4) | 0.2953 (3) | 0.0379 (15) | |
C5 | 0.2294 (2) | 0.1479 (4) | 0.2372 (3) | 0.0436 (16) | |
C6 | 0.1884 (2) | 0.1293 (4) | 0.1445 (3) | 0.0446 (16) | |
C7 | 0.2876 (2) | 0.1305 (4) | 0.4006 (3) | 0.0397 (16) | |
C8 | 0.2605 (2) | 0.0961 (4) | 0.5193 (3) | 0.0409 (16) | |
C9 | 0.2259 (2) | 0.1152 (4) | 0.5935 (3) | 0.0427 (16) | |
C10 | 0.2982 (2) | 0.2106 (4) | 0.5385 (3) | 0.0405 (16) | |
C11 | 0.3127 (2) | 0.1927 (4) | 0.4314 (3) | 0.0393 (16) | |
C12 | 0.3526 (2) | 0.2352 (4) | 0.3542 (3) | 0.0482 (16) | |
C13 | 0.3767 (2) | 0.2925 (4) | 0.3803 (4) | 0.0537 (17) | |
C14 | 0.3613 (2) | 0.3093 (4) | 0.4867 (4) | 0.0559 (17) | |
C15 | 0.3228 (2) | 0.2687 (4) | 0.5662 (4) | 0.0522 (17) | |
C16 | 0.1733 (2) | 0.1089 (4) | 0.5299 (4) | 0.0557 (16) | |
C17 | 0.2098 (2) | 0.0842 (4) | 0.7158 (4) | 0.060 (2) | |
C18 | 0.3354 (2) | 0.1183 (4) | 0.3632 (4) | 0.0539 (17) | |
O3 | −0.04570 | −0.01900 | 0.24870 | 0.2435* | 0.167 |
O4 | 0.04460 | 0.03370 | 0.30400 | 0.2586* | 0.167 |
C20 | −0.00850 | 0.01370 | 0.32610 | 0.2680* | 0.167 |
C21 | −0.01460 | −0.00360 | 0.46150 | 0.0634* | 0.167 |
C22 | 0.00410 | −0.04820 | 0.47850 | 0.2916* | 0.167 |
C23 | 0.02390 | 0.04920 | 0.53890 | 0.1376* | 0.167 |
H1 | 0.091 (4) | 0.013 (7) | 0.008 (7) | 0.17 (3)* | |
H2 | 0.1543 (2) | −0.0081 (4) | 0.1359 (4) | 0.054 (12)* | |
H3 | 0.2259 (2) | 0.0249 (4) | 0.2974 (4) | 0.069 (14)* | |
H4 | 0.2505 (2) | 0.1921 (4) | 0.2643 (3) | 0.070 (14)* | |
H5 | 0.1786 (2) | 0.1591 (4) | 0.1009 (3) | 0.053 (12)* | |
H6 | 0.2330 (2) | 0.0522 (4) | 0.4942 (3) | 0.046 (11)* | |
H7 | 0.2946 (2) | 0.0996 (4) | 0.5763 (3) | 0.063 (13)* | |
H8 | 0.3649 (2) | 0.2225 (4) | 0.2716 (3) | 0.058 (12)* | |
H9 | 0.4071 (2) | 0.3240 (4) | 0.3185 (4) | 0.055 (12)* | |
H10 | 0.3796 (2) | 0.3540 (4) | 0.5078 (4) | 0.063 (13)* | |
H11 | 0.3114 (2) | 0.2817 (4) | 0.6496 (4) | 0.069 (13)* | |
H12 | 0.1456 (2) | 0.0650 (4) | 0.5051 (4) | 0.099 (18)* | |
H13 | 0.1510 (2) | 0.1225 (4) | 0.5905 (4) | 0.068 (13)* | |
H14 | 0.1860 (2) | 0.1349 (4) | 0.4489 (4) | 0.090 (16)* | |
H15 | 0.1826 (2) | 0.0391 (4) | 0.7009 (4) | 0.068 (14)* | |
H16 | 0.2480 (2) | 0.0918 (4) | 0.7626 (4) | 0.070 (14)* | |
H17 | 0.1875 (2) | 0.0999 (4) | 0.7707 (4) | 0.067 (14)* | |
H18 | 0.3554 (2) | 0.1414 (4) | 0.2807 (4) | 0.087 (15)* | |
H19 | 0.3667 (2) | 0.1319 (4) | 0.4351 (4) | 0.059 (12)* | |
H20 | 0.3175 (2) | 0.0732 (4) | 0.3474 (4) | 0.079 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.058 (3) | 0.065 (2) | 0.0590 (17) | 0.024 (2) | −0.0186 (17) | −0.0096 (17) |
O2 | 0.056 (2) | 0.042 (2) | 0.0553 (16) | 0.0212 (19) | 0.0086 (15) | −0.0061 (15) |
C1 | 0.050 (3) | 0.046 (3) | 0.041 (2) | 0.022 (3) | −0.001 (2) | −0.002 (2) |
C2 | 0.055 (3) | 0.035 (3) | 0.050 (2) | 0.019 (3) | −0.004 (2) | −0.005 (2) |
C3 | 0.050 (3) | 0.037 (3) | 0.050 (2) | 0.022 (3) | −0.001 (2) | 0.000 (2) |
C4 | 0.043 (3) | 0.034 (3) | 0.0393 (19) | 0.021 (2) | 0.007 (2) | 0.0028 (19) |
C5 | 0.051 (3) | 0.034 (3) | 0.047 (2) | 0.022 (3) | −0.002 (2) | −0.001 (2) |
C6 | 0.055 (3) | 0.039 (3) | 0.046 (2) | 0.028 (3) | −0.003 (2) | −0.001 (2) |
C7 | 0.040 (3) | 0.038 (3) | 0.046 (2) | 0.023 (2) | −0.0002 (19) | 0.0025 (19) |
C8 | 0.041 (3) | 0.040 (3) | 0.043 (2) | 0.021 (2) | −0.003 (2) | 0.002 (2) |
C9 | 0.045 (3) | 0.037 (3) | 0.047 (2) | 0.021 (3) | 0.003 (2) | 0.001 (2) |
C10 | 0.040 (3) | 0.038 (3) | 0.047 (2) | 0.022 (2) | −0.004 (2) | −0.002 (2) |
C11 | 0.034 (3) | 0.032 (3) | 0.050 (2) | 0.015 (2) | −0.006 (2) | 0.002 (2) |
C12 | 0.043 (3) | 0.043 (3) | 0.050 (2) | 0.015 (3) | −0.005 (2) | 0.000 (2) |
C13 | 0.046 (3) | 0.041 (3) | 0.064 (3) | 0.014 (3) | −0.008 (3) | 0.005 (2) |
C14 | 0.053 (3) | 0.036 (3) | 0.076 (3) | 0.020 (3) | −0.016 (3) | −0.005 (3) |
C15 | 0.053 (3) | 0.045 (3) | 0.066 (3) | 0.030 (3) | −0.007 (2) | −0.011 (3) |
C16 | 0.050 (3) | 0.064 (3) | 0.062 (2) | 0.035 (3) | 0.003 (2) | −0.005 (2) |
C17 | 0.069 (4) | 0.061 (4) | 0.055 (2) | 0.035 (3) | 0.008 (3) | 0.010 (3) |
C18 | 0.050 (3) | 0.055 (3) | 0.066 (3) | 0.033 (3) | 0.001 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.39 (5) | C7—C11 | 1.51 (6) |
O2—C9 | 1.45 (5) | C7—C18 | 1.54 (6) |
O2—C10 | 1.37 (5) | C8—C9 | 1.51 (6) |
C1—C2 | 1.38 (5) | C9—C17 | 1.53 (6) |
C1—C6 | 1.37 (5) | C9—C16 | 1.52 (6) |
C2—C3 | 1.38 (5) | C10—C15 | 1.40 (5) |
C3—C4 | 1.39 (5) | C10—C11 | 1.40 (5) |
C4—C5 | 1.39 (5) | C11—C12 | 1.40 (5) |
C4—C7 | 1.55 (6) | C12—C13 | 1.38 (5) |
C5—C6 | 1.40 (5) | C13—C14 | 1.39 (5) |
C7—C8 | 1.56 (6) | C14—C15 | 1.38 (5) |
| | | |
O1···O1i | 2.83 (10) | O1···O1ii | 2.83 (10) |
| | | |
C9—O2—C10 | 117.4 (3) | C7—C8—C9 | 115.6 (5) |
O1—C1—C6 | 118.8 (5) | C16—C9—C17 | 110.4 (5) |
O1—C1—C2 | 121.6 (6) | O2—C9—C17 | 104.1 (4) |
C2—C1—C6 | 119.6 (5) | O2—C9—C8 | 109.0 (5) |
C1—C2—C3 | 120.4 (6) | O2—C9—C16 | 108.0 (5) |
C2—C3—C4 | 121.6 (6) | C8—C9—C16 | 114.9 (4) |
C3—C4—C5 | 117.0 (5) | C8—C9—C17 | 109.9 (5) |
C3—C4—C7 | 120.4 (6) | O2—C10—C11 | 124.7 (6) |
C5—C4—C7 | 122.7 (6) | C11—C10—C15 | 120.8 (5) |
C4—C5—C6 | 121.9 (6) | O2—C10—C15 | 114.4 (4) |
C1—C6—C5 | 119.6 (6) | C10—C11—C12 | 117.2 (6) |
C8—C7—C18 | 106.8 (5) | C7—C11—C12 | 121.0 (4) |
C11—C7—C18 | 110.0 (6) | C7—C11—C10 | 121.8 (5) |
C4—C7—C18 | 108.5 (4) | C11—C12—C13 | 122.4 (5) |
C4—C7—C8 | 111.5 (5) | C12—C13—C14 | 119.5 (6) |
C4—C7—C11 | 112.7 (5) | C13—C14—C15 | 120.0 (6) |
C8—C7—C11 | 107.2 (4) | C10—C15—C14 | 120.2 (5) |
| | | |
C10—O2—C9—C8 | 41.1 (6) | C4—C7—C11—C10 | 107.5 (6) |
C10—O2—C9—C16 | −84.4 (5) | C4—C7—C11—C12 | −73.7 (7) |
C10—O2—C9—C17 | 158.3 (5) | C8—C7—C11—C10 | −15.6 (8) |
C9—O2—C10—C11 | −15.2 (8) | C8—C7—C11—C12 | 163.2 (6) |
C9—O2—C10—C15 | 167.4 (5) | C18—C7—C11—C10 | −131.4 (6) |
O1—C1—C2—C3 | −178.2 (5) | C11—C7—C8—C9 | 43.9 (7) |
C2—C1—C6—C5 | −1.2 (8) | C18—C7—C8—C9 | 161.8 (5) |
C6—C1—C2—C3 | 1.0 (8) | C18—C7—C11—C12 | 47.5 (7) |
O1—C1—C6—C5 | 178.1 (5) | C7—C8—C9—C17 | −171.3 (5) |
C1—C2—C3—C4 | 0.3 (9) | C7—C8—C9—C16 | 63.6 (8) |
C2—C3—C4—C5 | −1.4 (8) | C7—C8—C9—O2 | −57.8 (6) |
C2—C3—C4—C7 | 178.2 (5) | O2—C10—C11—C7 | 1.7 (9) |
C3—C4—C5—C6 | 1.2 (8) | C15—C10—C11—C12 | 0.1 (9) |
C3—C4—C7—C11 | −179.4 (5) | O2—C10—C11—C12 | −177.2 (5) |
C3—C4—C7—C18 | 58.6 (7) | C15—C10—C11—C7 | 179.0 (6) |
C5—C4—C7—C8 | 120.8 (6) | C11—C10—C15—C14 | 0.9 (10) |
C5—C4—C7—C11 | 0.2 (7) | O2—C10—C15—C14 | 178.5 (5) |
C5—C4—C7—C18 | −121.8 (6) | C10—C11—C12—C13 | −0.6 (9) |
C3—C4—C7—C8 | −58.8 (7) | C7—C11—C12—C13 | −179.5 (6) |
C7—C4—C5—C6 | −178.4 (5) | C11—C12—C13—C14 | 0.1 (10) |
C4—C5—C6—C1 | 0.0 (8) | C12—C13—C14—C15 | 1.0 (9) |
C4—C7—C8—C9 | −79.9 (7) | C13—C14—C15—C10 | −1.5 (9) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
(DIH) [4-
p-hydroxyphenyl-2,2,4-trimethylchroman]-hexanoic acid
top
Crystal data top
6(C18H20O2)·(C6H12O2) | Dx = 1.207 Mg m−3 |
Mr = 1726.3 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.28 (2) Å | θ = 5–25° |
c = 10.98 (1) Å | µ = 0.08 mm−1 |
V = 7077 (10) Å3 | T = 293 K |
Z = 3 | Acicular,hexagonal prism, colourless |
F(000) = 2784 | 0.6 × 0.2 × 0.2 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.083 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ'fixed, where the angle θ' is the projection
of θ on the equatorial plane | k = −26→26 |
4423 measured reflections | l = 0→11 |
1582 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.076 | See text |
wR(F2) = 0.055 | w = 1/[σ2(F) + 0.000077F2] |
S = 1.14 | (Δ/σ)max = 0.0001 |
1249 reflections | Δρmax = 0.30 e Å−3 |
215 parameters | Δρmin = −0.16 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1221 (2) | 0.0570 (4) | 0.0169 (3) | 0.0692 (16) | |
O2 | 0.26210 (10) | 0.1751 (2) | 0.6262 (2) | 0.0530 (11) | |
C1 | 0.1631 (2) | 0.0744 (4) | 0.1094 (4) | 0.0478 (18) | |
C2 | 0.1765 (2) | 0.0367 (4) | 0.1636 (4) | 0.052 (2) | |
C3 | 0.2164 (2) | 0.0550 (4) | 0.2569 (4) | 0.0479 (16) | |
C4 | 0.2445 (2) | 0.1116 (4) | 0.2964 (3) | 0.0402 (16) | |
C5 | 0.2302 (2) | 0.1485 (4) | 0.2377 (3) | 0.0446 (16) | |
C6 | 0.1898 (2) | 0.1300 (4) | 0.1452 (3) | 0.0476 (16) | |
C7 | 0.2877 (2) | 0.1301 (4) | 0.4021 (3) | 0.0384 (16) | |
C8 | 0.2606 (2) | 0.0959 (4) | 0.5196 (3) | 0.0433 (16) | |
C9 | 0.2258 (2) | 0.1150 (4) | 0.5939 (3) | 0.0446 (16) | |
C10 | 0.2989 (2) | 0.2112 (4) | 0.5385 (3) | 0.0436 (16) | |
C11 | 0.3129 (2) | 0.1931 (4) | 0.4319 (3) | 0.0391 (16) | |
C12 | 0.3527 (2) | 0.2352 (4) | 0.3554 (4) | 0.0477 (17) | |
C13 | 0.3769 (2) | 0.2925 (4) | 0.3812 (4) | 0.0548 (19) | |
C14 | 0.3616 (2) | 0.3092 (4) | 0.4876 (4) | 0.057 (2) | |
C15 | 0.3230 (2) | 0.2689 (4) | 0.5666 (4) | 0.0514 (17) | |
C16 | 0.1738 (2) | 0.1093 (4) | 0.5294 (4) | 0.0552 (17) | |
C17 | 0.2094 (2) | 0.0838 (4) | 0.7157 (4) | 0.062 (2) | |
C18 | 0.3356 (2) | 0.1181 (4) | 0.3659 (4) | 0.0529 (17) | |
O3 | −0.00580 | 0.01020 | 0.12270 | 0.1421* | 0.167 |
O4 | 0.02330 | −0.03620 | 0.24050 | 0.1745* | 0.167 |
C20 | 0.01230 | 0.00380 | 0.22550 | 0.0581* | 0.167 |
C21 | −0.01330 | 0.01350 | 0.34150 | 0.1067* | 0.167 |
C22 | 0.01840 | 0.00930 | 0.45330 | 0.0352* | 0.167 |
C23 | −0.00910 | 0.01610 | 0.56950 | 0.1171* | 0.167 |
C24 | 0.02410 | 0.01430 | 0.68100 | 0.0982* | 0.167 |
C25 | −0.00440 | 0.01940 | 0.79750 | 0.2363* | 0.167 |
H1 | 0.110 (3) | 0.023 (6) | 0.015 (7) | 0.17 (4)* | |
H2 | 0.1560 (2) | −0.0069 (4) | 0.1339 (4) | 0.093 (16)* | |
H3 | 0.2258 (2) | 0.0250 (4) | 0.2998 (4) | 0.069 (13)* | |
H4 | 0.2512 (2) | 0.1924 (4) | 0.2647 (3) | 0.062 (13)* | |
H5 | 0.1798 (2) | 0.1596 (4) | 0.1021 (3) | 0.060 (13)* | |
H6 | 0.2332 (2) | 0.0523 (4) | 0.4940 (3) | 0.052 (12)* | |
H7 | 0.2942 (2) | 0.0991 (4) | 0.5770 (3) | 0.041 (10)* | |
H8 | 0.3652 (2) | 0.2226 (4) | 0.2732 (4) | 0.073 (13)* | |
H9 | 0.4069 (2) | 0.3238 (4) | 0.3190 (4) | 0.068 (13)* | |
H10 | 0.3800 (2) | 0.3536 (4) | 0.5089 (4) | 0.094 (16)* | |
H11 | 0.3115 (2) | 0.2818 (4) | 0.6497 (4) | 0.080 (14)* | |
H12 | 0.1461 (2) | 0.0656 (4) | 0.5044 (4) | 0.11 (2)* | |
H13 | 0.1516 (2) | 0.1230 (4) | 0.5893 (4) | 0.074 (14)* | |
H14 | 0.1869 (2) | 0.1352 (4) | 0.4484 (4) | 0.095 (16)* | |
H15 | 0.1824 (2) | 0.0390 (4) | 0.7002 (4) | 0.077 (15)* | |
H16 | 0.2471 (2) | 0.0911 (4) | 0.7633 (4) | 0.098 (18)* | |
H17 | 0.1870 (2) | 0.0993 (4) | 0.7699 (4) | 0.106 (18)* | |
H18 | 0.3558 (2) | 0.1411 (4) | 0.2839 (4) | 0.089 (15)* | |
H19 | 0.3664 (2) | 0.1312 (4) | 0.4383 (4) | 0.065 (13)* | |
H20 | 0.3177 (2) | 0.0732 (4) | 0.3498 (4) | 0.097 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.066 (3) | 0.072 (3) | 0.061 (2) | 0.028 (3) | −0.015 (2) | −0.0087 (19) |
O2 | 0.051 (2) | 0.046 (2) | 0.0578 (16) | 0.0211 (19) | 0.0060 (15) | −0.0076 (16) |
C1 | 0.046 (4) | 0.052 (3) | 0.042 (2) | 0.022 (3) | −0.006 (3) | −0.005 (2) |
C2 | 0.058 (4) | 0.036 (4) | 0.055 (3) | 0.018 (3) | −0.002 (3) | −0.003 (3) |
C3 | 0.051 (3) | 0.038 (3) | 0.053 (2) | 0.021 (3) | −0.004 (3) | −0.002 (3) |
C4 | 0.039 (3) | 0.032 (3) | 0.046 (2) | 0.015 (3) | 0.006 (2) | 0.001 (2) |
C5 | 0.044 (3) | 0.034 (3) | 0.051 (2) | 0.016 (3) | −0.002 (2) | −0.005 (2) |
C6 | 0.054 (3) | 0.040 (3) | 0.048 (2) | 0.023 (3) | −0.006 (3) | −0.003 (3) |
C7 | 0.039 (3) | 0.034 (3) | 0.046 (2) | 0.021 (3) | −0.001 (2) | 0.000 (2) |
C8 | 0.048 (3) | 0.043 (3) | 0.046 (2) | 0.028 (3) | −0.003 (2) | −0.002 (2) |
C9 | 0.042 (3) | 0.035 (3) | 0.051 (2) | 0.015 (3) | 0.001 (2) | 0.000 (2) |
C10 | 0.037 (3) | 0.040 (3) | 0.052 (2) | 0.018 (3) | 0.002 (2) | 0.005 (2) |
C11 | 0.038 (3) | 0.035 (3) | 0.044 (2) | 0.018 (3) | −0.006 (2) | −0.001 (2) |
C12 | 0.043 (3) | 0.037 (3) | 0.055 (3) | 0.014 (3) | −0.004 (2) | 0.002 (3) |
C13 | 0.051 (4) | 0.042 (3) | 0.063 (3) | 0.017 (3) | −0.003 (3) | 0.007 (3) |
C14 | 0.046 (4) | 0.033 (4) | 0.083 (3) | 0.014 (3) | −0.014 (3) | 0.000 (3) |
C15 | 0.049 (3) | 0.038 (3) | 0.069 (3) | 0.023 (3) | −0.009 (3) | −0.011 (3) |
C16 | 0.043 (3) | 0.065 (3) | 0.063 (3) | 0.031 (3) | −0.002 (3) | −0.006 (3) |
C17 | 0.067 (4) | 0.064 (4) | 0.055 (3) | 0.033 (4) | 0.015 (3) | 0.012 (3) |
C18 | 0.050 (3) | 0.051 (3) | 0.068 (3) | 0.033 (3) | 0.005 (3) | −0.002 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.406 (8) | C7—C8 | 1.547 (7) |
O2—C9 | 1.473 (8) | C7—C18 | 1.549 (10) |
O2—C10 | 1.384 (6) | C8—C9 | 1.527 (9) |
C1—C2 | 1.386 (9) | C9—C16 | 1.522 (9) |
C1—C6 | 1.371 (10) | C9—C17 | 1.527 (7) |
C2—C3 | 1.393 (8) | C10—C15 | 1.404 (10) |
C3—C4 | 1.406 (10) | C10—C11 | 1.396 (7) |
C4—C5 | 1.405 (9) | C11—C12 | 1.399 (9) |
C4—C7 | 1.548 (7) | C12—C13 | 1.388 (10) |
C5—C6 | 1.395 (8) | C13—C14 | 1.392 (8) |
C7—C11 | 1.534 (10) | C14—C15 | 1.383 (9) |
| | | |
O1···O1i | 2.911 (11) | O1···O1ii | 2.911 (12) |
| | | |
C9—O2—C10 | 118.0 (3) | C7—C8—C9 | 115.5 (5) |
O1—C1—C6 | 118.3 (6) | O2—C9—C17 | 104.8 (4) |
O1—C1—C2 | 121.3 (6) | C8—C9—C16 | 115.0 (4) |
C2—C1—C6 | 120.4 (5) | C8—C9—C17 | 109.7 (5) |
C1—C2—C3 | 119.9 (6) | C16—C9—C17 | 110.6 (5) |
C2—C3—C4 | 121.3 (6) | O2—C9—C16 | 107.4 (5) |
C3—C4—C7 | 119.8 (6) | O2—C9—C8 | 108.8 (5) |
C5—C4—C7 | 123.3 (6) | O2—C10—C15 | 114.3 (4) |
C3—C4—C5 | 116.8 (5) | O2—C10—C11 | 124.1 (6) |
C4—C5—C6 | 121.8 (6) | C11—C10—C15 | 121.6 (5) |
C1—C6—C5 | 119.7 (6) | C7—C11—C12 | 121.4 (4) |
C4—C7—C11 | 111.5 (5) | C10—C11—C12 | 116.8 (6) |
C4—C7—C18 | 108.9 (4) | C7—C11—C10 | 121.8 (5) |
C8—C7—C11 | 108.0 (4) | C11—C12—C13 | 122.6 (5) |
C8—C7—C18 | 106.6 (5) | C12—C13—C14 | 119.2 (6) |
C11—C7—C18 | 109.8 (6) | C13—C14—C15 | 120.0 (6) |
C4—C7—C8 | 111.9 (5) | C10—C15—C14 | 119.8 (5) |
| | | |
C10—O2—C9—C8 | 40.8 (6) | C4—C7—C11—C10 | 108.6 (6) |
C10—O2—C9—C16 | −84.3 (5) | C4—C7—C11—C12 | −73.8 (7) |
C10—O2—C9—C17 | 158.0 (5) | C8—C7—C11—C10 | −14.7 (8) |
C9—O2—C10—C11 | −14.4 (8) | C8—C7—C11—C12 | 162.9 (6) |
C9—O2—C10—C15 | 167.3 (5) | C18—C7—C11—C10 | −130.6 (6) |
O1—C1—C2—C3 | −178.6 (5) | C11—C7—C8—C9 | 43.5 (7) |
C2—C1—C6—C5 | −0.7 (9) | C18—C7—C8—C9 | 161.4 (5) |
C6—C1—C2—C3 | 1.4 (9) | C18—C7—C11—C12 | 47.0 (7) |
O1—C1—C6—C5 | 179.2 (5) | C7—C8—C9—C17 | −171.4 (5) |
C1—C2—C3—C4 | −1.2 (9) | C7—C8—C9—C16 | 63.2 (8) |
C2—C3—C4—C5 | 0.3 (8) | C7—C8—C9—O2 | −57.3 (6) |
C2—C3—C4—C7 | 178.8 (5) | O2—C10—C11—C7 | 0.4 (9) |
C3—C4—C5—C6 | 0.4 (8) | C15—C10—C11—C12 | 0.9 (9) |
C3—C4—C7—C11 | −179.3 (5) | O2—C10—C11—C12 | −177.3 (5) |
C3—C4—C7—C18 | 59.4 (7) | C15—C10—C11—C7 | 178.6 (6) |
C5—C4—C7—C8 | 120.2 (6) | C11—C10—C15—C14 | 0.0 (10) |
C5—C4—C7—C11 | −0.9 (7) | O2—C10—C15—C14 | 178.4 (5) |
C5—C4—C7—C18 | −122.2 (6) | C10—C11—C12—C13 | −1.2 (9) |
C3—C4—C7—C8 | −58.2 (7) | C7—C11—C12—C13 | −178.9 (6) |
C7—C4—C5—C6 | −178.0 (5) | C11—C12—C13—C14 | 0.5 (10) |
C4—C5—C6—C1 | −0.2 (8) | C12—C13—C14—C15 | 0.4 (10) |
C4—C7—C8—C9 | −79.6 (7) | C13—C14—C15—C10 | −0.7 (9) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
(DIE) [4-
p-hydroxyphenyl-2,2,4-trimethylchroman]-heptanoic acid
top
Crystal data top
6(C18H20O2)·(C7H14O2) | Dx = 1.204 Mg m−3 |
Mr = 1740.3 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.30 (2) Å | θ = 5–25° |
c = 11.07 (1) Å | µ = 0.08 mm−1 |
V = 7145 (10) Å3 | T = 293 K |
Z = 3 | Acicular,hexagonal prism, colourless |
F(000) = 2808 | 0.6 × 0.2 × 0.2 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.053 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ'fixed, where the angle θ' is the projection
of θ on the equatorial plane | k = −26→26 |
4458 measured reflections | l = 0→11 |
1626 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.058 | See text |
wR(F2) = 0.058 | w = 1/[σ2(F) + 0.00012F2] |
S = 1.28 | (Δ/σ)max = 0.001 |
1350 reflections | Δρmax = 0.45 e Å−3 |
215 parameters | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.12390 (10) | 0.0571 (3) | 0.0187 (3) | 0.0787 (15) | |
O2 | 0.26330 (10) | 0.1754 (2) | 0.6261 (2) | 0.0520 (11) | |
C1 | 0.1650 (2) | 0.0747 (4) | 0.1108 (4) | 0.0549 (18) | |
C2 | 0.1784 (2) | 0.0370 (4) | 0.1649 (4) | 0.0573 (19) | |
C3 | 0.2183 (2) | 0.0557 (4) | 0.2581 (3) | 0.0518 (16) | |
C4 | 0.2453 (2) | 0.1119 (4) | 0.2984 (3) | 0.0391 (15) | |
C5 | 0.2308 (2) | 0.1482 (4) | 0.2397 (3) | 0.0469 (16) | |
C6 | 0.1911 (2) | 0.1302 (4) | 0.1467 (3) | 0.0526 (16) | |
C7 | 0.2884 (2) | 0.1305 (4) | 0.4032 (3) | 0.0377 (16) | |
C8 | 0.2613 (2) | 0.0964 (4) | 0.5196 (3) | 0.0418 (16) | |
C9 | 0.2270 (2) | 0.1158 (4) | 0.5926 (3) | 0.0414 (16) | |
C10 | 0.2996 (2) | 0.2117 (4) | 0.5389 (3) | 0.0420 (16) | |
C11 | 0.3135 (2) | 0.1937 (4) | 0.4332 (3) | 0.0392 (16) | |
C12 | 0.3531 (2) | 0.2356 (4) | 0.3563 (3) | 0.0478 (16) | |
C13 | 0.3770 (2) | 0.2928 (4) | 0.3818 (4) | 0.0550 (17) | |
C14 | 0.3620 (2) | 0.3096 (4) | 0.4870 (4) | 0.0558 (17) | |
C15 | 0.3236 (2) | 0.2691 (4) | 0.5657 (4) | 0.0497 (17) | |
C16 | 0.1752 (2) | 0.1107 (4) | 0.5286 (4) | 0.0572 (17) | |
C17 | 0.2101 (2) | 0.0842 (4) | 0.7141 (4) | 0.062 (2) | |
C18 | 0.3365 (2) | 0.1189 (4) | 0.3683 (4) | 0.0544 (17) | |
O3 | 0.00060 | −0.01600 | 0.09610 | 0.1631* | 0.167 |
O4 | 0.04100 | 0.06690 | 0.18970 | 0.1883* | 0.167 |
C20 | 0.00890 | 0.01310 | 0.19230 | 0.1115* | 0.167 |
C21 | 0.00650 | −0.01510 | 0.31440 | 0.2211* | 0.167 |
C22 | 0.01630 | 0.02680 | 0.41730 | 0.1254* | 0.167 |
C23 | 0.01750 | −0.00010 | 0.53870 | 0.1049* | 0.167 |
C24 | 0.02050 | 0.03890 | 0.64250 | 0.1059* | 0.167 |
C25 | 0.02840 | 0.01540 | 0.76290 | 0.1235* | 0.167 |
C26 | −0.02280 | −0.04390 | 0.78410 | 0.2679* | 0.167 |
H1 | 0.128 (3) | 0.023 (5) | 0.021 (6) | 0.14 (3)* | |
H2 | 0.1581 (2) | −0.0065 (4) | 0.1353 (4) | 0.090 (15)* | |
H3 | 0.2285 (2) | 0.0262 (4) | 0.3000 (3) | 0.059 (12)* | |
H4 | 0.2509 (2) | 0.1920 (4) | 0.2680 (3) | 0.072 (13)* | |
H5 | 0.1817 (2) | 0.1599 (4) | 0.1027 (3) | 0.080 (14)* | |
H6 | 0.2338 (2) | 0.0527 (4) | 0.4946 (3) | 0.048 (11)* | |
H7 | 0.2949 (2) | 0.0996 (4) | 0.5766 (3) | 0.042 (10)* | |
H8 | 0.3655 (2) | 0.2231 (4) | 0.2745 (3) | 0.055 (11)* | |
H9 | 0.4066 (2) | 0.3240 (4) | 0.3196 (4) | 0.057 (11)* | |
H10 | 0.3805 (2) | 0.3540 (4) | 0.5082 (4) | 0.072 (13)* | |
H11 | 0.3119 (2) | 0.2820 (4) | 0.6479 (4) | 0.049 (10)* | |
H12 | 0.1475 (2) | 0.0672 (4) | 0.5030 (4) | 0.095 (17)* | |
H13 | 0.1530 (2) | 0.1241 (4) | 0.5888 (4) | 0.093 (15)* | |
H14 | 0.1882 (2) | 0.1369 (4) | 0.4488 (4) | 0.116 (18)* | |
H15 | 0.1829 (2) | 0.0396 (4) | 0.6981 (4) | 0.085 (15)* | |
H16 | 0.2476 (2) | 0.0911 (4) | 0.7614 (4) | 0.110 (19)* | |
H17 | 0.1879 (2) | 0.0999 (4) | 0.7681 (4) | 0.078 (14)* | |
H18 | 0.3568 (2) | 0.1419 (4) | 0.2869 (4) | 0.068 (12)* | |
H19 | 0.3672 (2) | 0.1325 (4) | 0.4405 (4) | 0.073 (13)* | |
H20 | 0.3189 (2) | 0.0741 (4) | 0.3529 (4) | 0.091 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.076 (3) | 0.085 (3) | 0.0615 (19) | 0.030 (2) | −0.018 (2) | −0.0116 (19) |
O2 | 0.051 (2) | 0.044 (2) | 0.0561 (15) | 0.0201 (17) | 0.0072 (15) | −0.0067 (15) |
C1 | 0.050 (4) | 0.059 (3) | 0.042 (2) | 0.017 (3) | −0.001 (3) | 0.000 (2) |
C2 | 0.060 (4) | 0.039 (3) | 0.056 (3) | 0.012 (3) | 0.001 (3) | −0.011 (3) |
C3 | 0.054 (3) | 0.043 (3) | 0.054 (2) | 0.021 (3) | 0.002 (2) | −0.001 (2) |
C4 | 0.040 (3) | 0.033 (3) | 0.0387 (19) | 0.014 (2) | 0.006 (2) | −0.004 (2) |
C5 | 0.047 (3) | 0.046 (3) | 0.046 (2) | 0.022 (3) | −0.002 (2) | −0.002 (2) |
C6 | 0.053 (3) | 0.049 (3) | 0.051 (2) | 0.022 (3) | −0.001 (3) | 0.001 (2) |
C7 | 0.038 (3) | 0.032 (3) | 0.045 (2) | 0.019 (2) | 0.005 (2) | 0.003 (2) |
C8 | 0.041 (3) | 0.037 (3) | 0.052 (2) | 0.023 (2) | 0.001 (2) | −0.001 (2) |
C9 | 0.038 (3) | 0.034 (3) | 0.047 (2) | 0.014 (3) | −0.001 (2) | 0.000 (2) |
C10 | 0.038 (3) | 0.043 (3) | 0.046 (2) | 0.021 (2) | −0.001 (2) | 0.003 (2) |
C11 | 0.038 (3) | 0.037 (3) | 0.043 (2) | 0.019 (2) | −0.005 (2) | −0.001 (2) |
C12 | 0.045 (3) | 0.040 (3) | 0.050 (2) | 0.015 (3) | −0.002 (2) | 0.001 (2) |
C13 | 0.052 (3) | 0.038 (3) | 0.065 (3) | 0.015 (3) | −0.006 (3) | 0.004 (3) |
C14 | 0.049 (3) | 0.034 (3) | 0.082 (3) | 0.019 (3) | −0.019 (3) | −0.007 (3) |
C15 | 0.049 (3) | 0.039 (3) | 0.065 (3) | 0.025 (3) | −0.007 (2) | −0.010 (3) |
C16 | 0.043 (3) | 0.067 (3) | 0.065 (3) | 0.030 (3) | −0.001 (3) | −0.004 (3) |
C17 | 0.065 (4) | 0.064 (4) | 0.055 (2) | 0.031 (3) | 0.016 (3) | 0.013 (3) |
C18 | 0.053 (3) | 0.053 (3) | 0.066 (3) | 0.033 (3) | 0.011 (2) | 0.000 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.411 (7) | C7—C11 | 1.541 (10) |
O2—C9 | 1.468 (8) | C7—C8 | 1.545 (7) |
O2—C10 | 1.383 (6) | C8—C9 | 1.519 (9) |
C1—C2 | 1.389 (9) | C9—C17 | 1.539 (7) |
C1—C6 | 1.372 (10) | C9—C16 | 1.525 (9) |
C2—C3 | 1.398 (8) | C10—C11 | 1.393 (7) |
C3—C4 | 1.402 (10) | C10—C15 | 1.395 (10) |
C4—C5 | 1.398 (9) | C11—C12 | 1.402 (9) |
C4—C7 | 1.546 (7) | C12—C13 | 1.387 (10) |
C5—C6 | 1.394 (8) | C13—C14 | 1.386 (8) |
C7—C18 | 1.546 (10) | C14—C15 | 1.386 (9) |
| | | |
O1···O1i | 2.961 (8) | O1···O1ii | 2.961 (7) |
| | | |
C9—O2—C10 | 117.6 (3) | C7—C8—C9 | 115.3 (5) |
C2—C1—C6 | 120.7 (5) | C8—C9—C17 | 109.5 (5) |
O1—C1—C6 | 118.1 (6) | C16—C9—C17 | 110.5 (5) |
O1—C1—C2 | 121.2 (6) | O2—C9—C17 | 104.3 (4) |
C1—C2—C3 | 119.6 (6) | C8—C9—C16 | 115.2 (4) |
C2—C3—C4 | 121.4 (6) | O2—C9—C16 | 107.5 (5) |
C5—C4—C7 | 123.7 (6) | O2—C9—C8 | 109.2 (5) |
C3—C4—C7 | 119.7 (6) | O2—C10—C15 | 115.0 (4) |
C3—C4—C5 | 116.6 (5) | O2—C10—C11 | 123.9 (6) |
C4—C5—C6 | 122.6 (6) | C11—C10—C15 | 121.1 (5) |
C1—C6—C5 | 119.1 (6) | C10—C11—C12 | 117.2 (6) |
C8—C7—C11 | 107.8 (4) | C7—C11—C10 | 121.9 (5) |
C11—C7—C18 | 109.6 (6) | C7—C11—C12 | 120.8 (4) |
C4—C7—C11 | 111.6 (5) | C11—C12—C13 | 122.1 (5) |
C8—C7—C18 | 106.6 (5) | C12—C13—C14 | 119.5 (6) |
C4—C7—C8 | 111.8 (5) | C13—C14—C15 | 119.7 (6) |
C4—C7—C18 | 109.3 (4) | C10—C15—C14 | 120.4 (5) |
| | | |
C10—O2—C9—C8 | 42.3 (6) | C4—C7—C11—C10 | 108.8 (6) |
C10—O2—C9—C16 | −83.3 (5) | C4—C7—C11—C12 | −73.5 (7) |
C10—O2—C9—C17 | 159.3 (5) | C8—C7—C11—C10 | −14.4 (8) |
C9—O2—C10—C11 | −15.6 (8) | C8—C7—C11—C12 | 163.3 (6) |
C9—O2—C10—C15 | 166.4 (5) | C18—C7—C11—C10 | −130.0 (6) |
O1—C1—C2—C3 | −178.3 (5) | C11—C7—C8—C9 | 43.0 (7) |
C2—C1—C6—C5 | −0.9 (9) | C18—C7—C8—C9 | 160.6 (5) |
C6—C1—C2—C3 | 0.9 (9) | C18—C7—C11—C12 | 47.7 (6) |
O1—C1—C6—C5 | 178.4 (5) | C7—C8—C9—C17 | −171.7 (5) |
C1—C2—C3—C4 | −0.1 (9) | C7—C8—C9—C16 | 63.0 (8) |
C2—C3—C4—C5 | −0.8 (8) | C7—C8—C9—O2 | −58.0 (6) |
C2—C3—C4—C7 | 179.0 (5) | O2—C10—C11—C7 | 0.9 (9) |
C3—C4—C5—C6 | 0.8 (8) | C15—C10—C11—C12 | 0.9 (9) |
C3—C4—C7—C11 | 179.6 (5) | O2—C10—C11—C12 | −176.9 (5) |
C3—C4—C7—C18 | 58.2 (7) | C15—C10—C11—C7 | 178.7 (6) |
C5—C4—C7—C8 | 120.2 (6) | C11—C10—C15—C14 | 0.0 (10) |
C5—C4—C7—C11 | −0.6 (8) | O2—C10—C15—C14 | 178.0 (5) |
C5—C4—C7—C18 | −122.0 (6) | C10—C11—C12—C13 | −1.3 (9) |
C3—C4—C7—C8 | −59.5 (7) | C7—C11—C12—C13 | −179.1 (6) |
C7—C4—C5—C6 | −178.9 (5) | C11—C12—C13—C14 | 0.6 (10) |
C4—C5—C6—C1 | 0.0 (9) | C12—C13—C14—C15 | 0.4 (9) |
C4—C7—C8—C9 | −80.0 (7) | C13—C14—C15—C10 | −0.7 (10) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 0.99 (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 m−3 |
Mr = 1754.4 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.30 (2) Å | θ = 5–25° |
c = 11.20 (1) Å | µ = 0.08 mm−1 |
V = 7229 (10) Å3 | T = 293 K |
Z = 3 | Acicular, hexagonal prism, colourless |
F(000) = 2832 | 0.5 × 0.15 × 0.15 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.043 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ'fixed, where the angle θ' is the projection
of θ on the equatorial plane | k = −26→26 |
4242 measured reflections | l = 0→11 |
1588 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.094 | See text |
wR(F2) = 0.085 | w = 1/[σ2(F) + 0.00016F2] |
S = 1.28 | (Δ/σ)max < 0.001 |
1037 reflections | Δρmax = 0.52 e Å−3 |
215 parameters | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1265 (4) | 0.0572 (8) | 0.0191 (7) | 0.103 (4) | |
O2 | 0.2637 (3) | 0.1757 (6) | 0.6255 (5) | 0.060 (3) | |
C1 | 0.1672 (5) | 0.0754 (11) | 0.1114 (10) | 0.074 (5) | |
C2 | 0.1807 (5) | 0.0376 (11) | 0.1629 (10) | 0.074 (5) | |
C3 | 0.2195 (5) | 0.0551 (10) | 0.2586 (9) | 0.065 (5) | |
C4 | 0.2466 (4) | 0.1117 (8) | 0.3016 (7) | 0.051 (4) | |
C5 | 0.2319 (4) | 0.1481 (9) | 0.2425 (8) | 0.058 (4) | |
C6 | 0.1934 (5) | 0.1308 (10) | 0.1495 (9) | 0.067 (5) | |
C7 | 0.2890 (4) | 0.1303 (8) | 0.4063 (8) | 0.050 (4) | |
C8 | 0.2612 (4) | 0.0967 (7) | 0.5205 (7) | 0.040 (3) | |
C9 | 0.2263 (4) | 0.1161 (8) | 0.5932 (8) | 0.048 (4) | |
C10 | 0.3000 (4) | 0.2117 (8) | 0.5370 (9) | 0.052 (4) | |
C11 | 0.3136 (4) | 0.1935 (8) | 0.4342 (8) | 0.045 (4) | |
C12 | 0.3531 (4) | 0.2356 (8) | 0.3585 (9) | 0.059 (4) | |
C13 | 0.3770 (4) | 0.2936 (8) | 0.3846 (10) | 0.063 (4) | |
C14 | 0.3619 (4) | 0.3092 (8) | 0.4882 (10) | 0.063 (5) | |
C15 | 0.3237 (4) | 0.2691 (8) | 0.5671 (8) | 0.059 (4) | |
C16 | 0.1757 (4) | 0.1112 (8) | 0.5278 (9) | 0.065 (4) | |
C17 | 0.2096 (5) | 0.0846 (10) | 0.7139 (8) | 0.066 (4) | |
C18 | 0.3384 (4) | 0.1199 (8) | 0.3713 (10) | 0.069 (4) | |
O3 | 0.01900 | 0.05700 | 0.17000 | 0.2914* | 0.167 |
O4 | −0.04100 | −0.03500 | 0.11000 | 0.2042* | 0.167 |
C20 | 0.00600 | 0.00900 | 0.16430 | 0.1382* | 0.167 |
C21 | 0.05200 | 0.00050 | 0.22320 | 0.2493* | 0.167 |
C22 | 0.04830 | 0.00380 | 0.35990 | 0.2712* | 0.167 |
C23 | −0.01370 | −0.03310 | 0.39920 | 0.0816* | 0.167 |
C24 | −0.01730 | −0.03070 | 0.53620 | 0.0374* | 0.167 |
C25 | 0.00370 | 0.03080 | 0.57480 | 0.2078* | 0.167 |
C26 | −0.00090 | 0.03300 | 0.71150 | 0.1134* | 0.167 |
C27 | 0.03690 | 0.01270 | 0.77040 | 0.0535* | 0.167 |
H1 | 0.144 (4) | 0.027 (9) | 0.017 (8) | 0.10 (4)* | |
H2 | 0.1613 (5) | −0.0055 (11) | 0.1312 (10) | 0.10 (4)* | |
H3 | 0.2286 (5) | 0.0249 (10) | 0.3005 (9) | 0.07 (3)* | |
H4 | 0.2515 (4) | 0.1917 (9) | 0.2707 (8) | 0.06 (3)* | |
H5 | 0.1840 (5) | 0.1609 (10) | 0.1080 (9) | 0.08 (3)* | |
H6 | 0.2336 (4) | 0.0529 (7) | 0.4961 (7) | 0.09 (3)* | |
H7 | 0.2946 (4) | 0.0999 (7) | 0.5776 (7) | 0.025 (19)* | |
H8 | 0.3654 (4) | 0.2229 (8) | 0.2777 (9) | 0.09 (3)* | |
H9 | 0.4068 (4) | 0.3250 (8) | 0.3237 (10) | 0.06 (3)* | |
H10 | 0.3804 (4) | 0.3537 (8) | 0.5086 (10) | 0.08 (3)* | |
H11 | 0.3126 (4) | 0.2823 (8) | 0.6488 (8) | 0.06 (3)* | |
H12 | 0.1475 (4) | 0.0675 (8) | 0.5033 (9) | 0.17 (6)* | |
H13 | 0.1537 (4) | 0.1255 (8) | 0.5856 (9) | 0.05 (3)* | |
H14 | 0.1894 (4) | 0.1369 (8) | 0.4482 (9) | 0.06 (3)* | |
H15 | 0.1818 (5) | 0.0400 (10) | 0.6981 (8) | 0.11 (4)* | |
H16 | 0.2471 (5) | 0.0909 (10) | 0.7597 (8) | 0.20 (7)* | |
H17 | 0.1881 (5) | 0.1008 (10) | 0.7681 (8) | 0.10 (4)* | |
H18 | 0.3584 (4) | 0.1428 (8) | 0.2906 (10) | 0.10 (4)* | |
H19 | 0.3691 (4) | 0.1340 (8) | 0.4425 (10) | 0.13 (5)* | |
H20 | 0.3215 (4) | 0.0752 (8) | 0.3566 (10) | 0.08 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.098 (9) | 0.122 (7) | 0.081 (5) | 0.048 (7) | −0.025 (6) | −0.023 (5) |
O2 | 0.046 (5) | 0.043 (5) | 0.081 (4) | 0.014 (4) | 0.005 (4) | −0.006 (4) |
C1 | 0.076 (11) | 0.083 (10) | 0.060 (7) | 0.037 (9) | 0.008 (8) | 0.005 (7) |
C2 | 0.056 (12) | 0.057 (8) | 0.071 (7) | 0.000 (9) | −0.008 (8) | −0.020 (7) |
C3 | 0.077 (9) | 0.032 (9) | 0.083 (7) | 0.024 (8) | 0.022 (7) | 0.004 (7) |
C4 | 0.045 (7) | 0.045 (7) | 0.064 (6) | 0.023 (6) | 0.009 (6) | 0.006 (6) |
C5 | 0.050 (9) | 0.053 (8) | 0.057 (6) | 0.016 (7) | −0.013 (6) | −0.013 (6) |
C6 | 0.089 (10) | 0.046 (10) | 0.061 (7) | 0.031 (8) | 0.007 (7) | 0.002 (7) |
C7 | 0.043 (7) | 0.036 (7) | 0.074 (6) | 0.023 (6) | 0.001 (5) | −0.006 (6) |
C8 | 0.033 (6) | 0.043 (6) | 0.051 (5) | 0.025 (6) | 0.001 (5) | 0.008 (5) |
C9 | 0.037 (7) | 0.035 (7) | 0.070 (6) | 0.017 (6) | 0.006 (6) | −0.004 (6) |
C10 | 0.040 (7) | 0.037 (7) | 0.075 (7) | 0.016 (6) | −0.001 (6) | 0.007 (6) |
C11 | 0.041 (7) | 0.038 (7) | 0.057 (6) | 0.020 (6) | −0.002 (6) | −0.002 (5) |
C12 | 0.058 (8) | 0.039 (8) | 0.078 (7) | 0.022 (7) | 0.002 (6) | 0.009 (6) |
C13 | 0.053 (8) | 0.054 (8) | 0.080 (7) | 0.025 (7) | −0.005 (7) | 0.004 (7) |
C14 | 0.062 (8) | 0.047 (9) | 0.080 (7) | 0.028 (7) | −0.008 (6) | 0.000 (7) |
C15 | 0.051 (8) | 0.056 (8) | 0.070 (7) | 0.026 (7) | 0.002 (6) | −0.004 (6) |
C16 | 0.046 (8) | 0.076 (7) | 0.081 (7) | 0.037 (7) | 0.003 (7) | −0.002 (6) |
C17 | 0.065 (9) | 0.067 (8) | 0.066 (6) | 0.032 (8) | 0.015 (7) | 0.013 (7) |
C18 | 0.059 (7) | 0.053 (8) | 0.107 (8) | 0.038 (7) | 0.019 (6) | 0.008 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.414 (18) | C7—C11 | 1.54 (2) |
O2—C9 | 1.470 (17) | C7—C18 | 1.561 (19) |
O2—C10 | 1.399 (15) | C8—C9 | 1.535 (17) |
C1—C6 | 1.38 (2) | C9—C17 | 1.544 (15) |
C1—C2 | 1.38 (2) | C9—C16 | 1.509 (18) |
C2—C3 | 1.41 (2) | C10—C11 | 1.377 (16) |
C3—C4 | 1.42 (2) | C10—C15 | 1.40 (2) |
C4—C7 | 1.544 (16) | C11—C12 | 1.401 (18) |
C4—C5 | 1.409 (18) | C12—C13 | 1.41 (2) |
C5—C6 | 1.384 (18) | C13—C14 | 1.369 (17) |
C7—C8 | 1.535 (14) | C14—C15 | 1.388 (18) |
| | | |
O1···O1i | 3.03 (2) | O1···O1ii | 3.03 (2) |
| | | |
C9—O2—C10 | 117.4 (8) | C7—C8—C9 | 116.3 (10) |
C2—C1—C6 | 120.3 (14) | O2—C9—C8 | 107.8 (10) |
O1—C1—C6 | 119.8 (15) | O2—C9—C17 | 104.4 (9) |
O1—C1—C2 | 119.9 (16) | C8—C9—C16 | 114.2 (8) |
C1—C2—C3 | 119.9 (16) | C8—C9—C17 | 109.5 (11) |
C2—C3—C4 | 121.3 (14) | C16—C9—C17 | 111.9 (11) |
C5—C4—C7 | 123.8 (12) | O2—C9—C16 | 108.4 (11) |
C3—C4—C7 | 120.8 (12) | C11—C10—C15 | 123.1 (12) |
C3—C4—C5 | 115.5 (11) | O2—C10—C11 | 124.3 (12) |
C4—C5—C6 | 123.2 (13) | O2—C10—C15 | 112.5 (9) |
C1—C6—C5 | 119.8 (14) | C7—C11—C10 | 122.0 (11) |
C8—C7—C18 | 108.3 (10) | C7—C11—C12 | 121.5 (10) |
C4—C7—C8 | 111.8 (11) | C10—C11—C12 | 116.5 (13) |
C4—C7—C11 | 111.0 (10) | C11—C12—C13 | 122.0 (11) |
C11—C7—C18 | 108.8 (11) | C12—C13—C14 | 118.9 (12) |
C8—C7—C11 | 108.0 (8) | C13—C14—C15 | 121.3 (13) |
C4—C7—C18 | 108.9 (9) | C10—C15—C14 | 118.2 (10) |
| | | |
C10—O2—C9—C8 | 43.1 (13) | C4—C7—C11—C10 | 110.0 (13) |
C10—O2—C9—C16 | −81.0 (12) | C4—C7—C11—C12 | −72.9 (15) |
C10—O2—C9—C17 | 159.5 (11) | C8—C7—C11—C10 | −12.8 (17) |
C9—O2—C10—C11 | −17.2 (18) | C8—C7—C11—C12 | 164.3 (12) |
C9—O2—C10—C15 | 165.8 (11) | C18—C7—C11—C10 | −130.2 (12) |
O1—C1—C2—C3 | −177.2 (13) | C11—C7—C8—C9 | 42.1 (14) |
C2—C1—C6—C5 | −2 (2) | C18—C7—C8—C9 | 159.8 (10) |
C6—C1—C2—C3 | 3 (2) | C18—C7—C11—C12 | 46.9 (14) |
O1—C1—C6—C5 | 177.9 (12) | C7—C8—C9—C17 | −170.9 (11) |
C1—C2—C3—C4 | −2 (2) | C7—C8—C9—C16 | 62.6 (15) |
C2—C3—C4—C5 | 0.1 (19) | C7—C8—C9—O2 | −57.9 (12) |
C2—C3—C4—C7 | −179.9 (12) | O2—C10—C11—C7 | 1 (2) |
C3—C4—C5—C6 | 0.6 (18) | C15—C10—C11—C12 | 0.0 (19) |
C3—C4—C7—C11 | 178.6 (11) | O2—C10—C11—C12 | −176.6 (12) |
C3—C4—C7—C18 | 58.9 (15) | C15—C10—C11—C7 | 177.2 (12) |
C5—C4—C7—C8 | 119.2 (13) | C11—C10—C15—C14 | 1 (2) |
C5—C4—C7—C11 | −1.4 (16) | O2—C10—C15—C14 | 178.1 (11) |
C5—C4—C7—C18 | −121.2 (13) | C10—C11—C12—C13 | −1.2 (19) |
C3—C4—C7—C8 | −60.8 (15) | C7—C11—C12—C13 | −178.4 (12) |
C7—C4—C5—C6 | −179.3 (12) | C11—C12—C13—C14 | 1 (2) |
C4—C5—C6—C1 | 0 (2) | C12—C13—C14—C15 | 0 (2) |
C4—C7—C8—C9 | −80.3 (13) | C13—C14—C15—C10 | −1.0 (19) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 1.14 (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 m−3 |
Mr = 919.02 | Melting point: not measured K |
Trigonal, R3 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -R 3 | Cell parameters from 15 reflections |
a = 27.19 (2) Å | θ = 5–22.5° |
c = 11.097 (10) Å | µ = 0.09 mm−1 |
V = 7105 (10) Å3 | T = 293 K |
Z = 6 | Acicular, hexagonal prism, colourless |
F(000) = 2928 | 0.40 × 0.12 × 0.12 mm |
Data collection top
Stoe STADI-2 two circle diffractometer | Rint = 0.109 |
Radiation source: fine focus sealed tube | θmax = 22.5°, θmin = 1.5° |
Graphite monochromator | h = −26→26 |
variable ω scan 2θ' fixed, where the angle θ' is the projection
of θ on the equatorial plane | k = −25→26 |
4176 measured reflections | l = 0→11 |
1521 independent reflections | Standard 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 F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.091 | See text |
wR(F2) = 0.083 | w = 1/[σ2(F) + 0.00019F2] |
S = 1.81 | (Δ/σ)max = 0.001 |
1013 reflections | Δρmax = 0.58 e Å−3 |
215 parameters | Δρmin = −0.32 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1229 (4) | 0.0575 (8) | 0.0181 (8) | 0.085 (4) | |
O2 | 0.2624 (2) | 0.1751 (4) | 0.6242 (5) | 0.057 (2) | |
C1 | 0.1638 (4) | 0.0736 (8) | 0.1079 (8) | 0.057 (4) | |
C2 | 0.1768 (4) | 0.0358 (8) | 0.1633 (8) | 0.057 (4) | |
C3 | 0.2169 (4) | 0.0549 (8) | 0.2557 (7) | 0.053 (3) | |
C4 | 0.2446 (3) | 0.1116 (7) | 0.2969 (7) | 0.048 (3) | |
C5 | 0.2301 (4) | 0.1481 (8) | 0.2388 (7) | 0.047 (3) | |
C6 | 0.1901 (4) | 0.1294 (8) | 0.1474 (7) | 0.050 (4) | |
C7 | 0.2880 (3) | 0.1302 (6) | 0.4021 (7) | 0.044 (3) | |
C8 | 0.2609 (4) | 0.0962 (7) | 0.5196 (6) | 0.047 (3) | |
C9 | 0.2254 (4) | 0.1147 (8) | 0.5916 (7) | 0.048 (3) | |
C10 | 0.2989 (3) | 0.2110 (7) | 0.5360 (8) | 0.048 (3) | |
C11 | 0.3126 (4) | 0.1929 (7) | 0.4309 (7) | 0.045 (3) | |
C12 | 0.3523 (4) | 0.2351 (8) | 0.3559 (8) | 0.058 (4) | |
C13 | 0.3765 (4) | 0.2920 (8) | 0.3827 (8) | 0.058 (4) | |
C14 | 0.3616 (4) | 0.3094 (8) | 0.4872 (8) | 0.064 (4) | |
C15 | 0.3229 (4) | 0.2685 (8) | 0.5662 (8) | 0.059 (4) | |
C16 | 0.1733 (4) | 0.1087 (8) | 0.5292 (8) | 0.062 (4) | |
C17 | 0.2099 (4) | 0.0837 (8) | 0.7142 (7) | 0.067 (4) | |
C18 | 0.3360 (3) | 0.1188 (7) | 0.3643 (8) | 0.057 (3) | |
F1 | −0.0099 (15) | −0.039 (2) | 0.411 (3) | 0.275 (18)* | 0.333 |
F2 | 0.0281 (15) | −0.044 (2) | 0.239 (3) | 0.156 (8)* | 0.333 |
F3 | 0.0645 (15) | 0.037 (2) | 0.339 (3) | 0.144 (8)* | 0.333 |
O3 | −0.0166 (15) | 0.052 (2) | 0.292 (3) | 0.72 (9)* | 0.333 |
O4 | −0.0107 (15) | 0.025 (2) | 0.133 (3) | 0.34 (3)* | 0.333 |
C20 | −0.0236 (15) | 0.005 (2) | 0.242 (3) | 0.25 (3)* | 0.333 |
C21 | 0.0161 (15) | −0.011 (2) | 0.310 (3) | 0.34 (3)* | 0.333 |
H1 | 0.114 (3) | 0.030 (6) | 0.027 (6) | 0.00 (2)* | |
H2 | 0.1560 (4) | −0.0081 (8) | 0.1359 (8) | 0.18 (5)* | |
H3 | 0.2275 (4) | 0.0255 (8) | 0.2972 (7) | 0.07 (3)* | |
H4 | 0.2502 (4) | 0.1920 (8) | 0.2661 (7) | 0.09 (3)* | |
H5 | 0.1800 (4) | 0.1591 (8) | 0.1054 (7) | 0.06 (2)* | |
H6 | 0.2337 (4) | 0.0522 (7) | 0.4946 (6) | 0.07 (3)* | |
H7 | 0.2947 (4) | 0.0999 (7) | 0.5769 (6) | 0.05 (2)* | |
H8 | 0.3652 (4) | 0.2229 (8) | 0.2744 (8) | 0.038 (19)* | |
H9 | 0.4067 (4) | 0.3236 (8) | 0.3217 (8) | 0.04 (2)* | |
H10 | 0.3797 (4) | 0.3540 (8) | 0.5077 (8) | 0.07 (3)* | |
H11 | 0.3116 (4) | 0.2810 (8) | 0.6494 (8) | 0.07 (2)* | |
H12 | 0.1457 (4) | 0.0649 (8) | 0.5042 (8) | 0.11 (4)* | |
H13 | 0.1510 (4) | 0.1221 (8) | 0.5895 (8) | 0.06 (2)* | |
H14 | 0.1860 (4) | 0.1350 (8) | 0.4494 (8) | 0.13 (4)* | |
H15 | 0.1825 (4) | 0.0386 (8) | 0.7007 (7) | 0.14 (4)* | |
H16 | 0.2483 (4) | 0.0913 (8) | 0.7590 (7) | 0.08 (3)* | |
H17 | 0.1883 (4) | 0.0998 (8) | 0.7692 (7) | 0.08 (3)* | |
H18 | 0.3559 (3) | 0.1423 (7) | 0.2831 (8) | 0.08 (3)* | |
H19 | 0.3674 (3) | 0.1321 (7) | 0.4352 (8) | 0.05 (2)* | |
H20 | 0.3182 (3) | 0.0740 (7) | 0.3477 (8) | 0.09 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.071 (7) | 0.065 (6) | 0.111 (6) | 0.027 (6) | −0.022 (5) | −0.007 (5) |
O2 | 0.048 (5) | 0.043 (4) | 0.074 (3) | 0.018 (4) | 0.010 (3) | −0.008 (3) |
C1 | 0.043 (8) | 0.055 (7) | 0.070 (6) | 0.023 (6) | −0.003 (6) | 0.004 (5) |
C2 | 0.044 (8) | 0.047 (7) | 0.071 (5) | 0.015 (6) | −0.005 (6) | 0.000 (5) |
C3 | 0.042 (7) | 0.038 (6) | 0.079 (5) | 0.021 (6) | 0.003 (5) | 0.000 (5) |
C4 | 0.031 (7) | 0.034 (6) | 0.074 (5) | 0.013 (5) | 0.010 (5) | 0.005 (5) |
C5 | 0.037 (7) | 0.033 (6) | 0.069 (5) | 0.015 (5) | −0.001 (5) | 0.000 (5) |
C6 | 0.047 (7) | 0.038 (7) | 0.066 (5) | 0.021 (6) | −0.001 (5) | 0.000 (5) |
C7 | 0.028 (6) | 0.029 (6) | 0.075 (5) | 0.014 (5) | −0.008 (5) | −0.005 (5) |
C8 | 0.046 (6) | 0.037 (6) | 0.065 (5) | 0.025 (5) | −0.004 (5) | 0.006 (5) |
C9 | 0.038 (6) | 0.028 (6) | 0.074 (5) | 0.013 (6) | 0.003 (5) | −0.008 (5) |
C10 | 0.028 (6) | 0.040 (6) | 0.080 (6) | 0.021 (5) | 0.004 (5) | 0.006 (5) |
C11 | 0.033 (6) | 0.025 (6) | 0.071 (5) | 0.011 (5) | −0.004 (5) | −0.002 (5) |
C12 | 0.050 (7) | 0.030 (7) | 0.087 (6) | 0.015 (6) | −0.004 (5) | −0.003 (6) |
C13 | 0.038 (7) | 0.037 (6) | 0.086 (6) | 0.009 (6) | 0.000 (6) | 0.007 (5) |
C14 | 0.058 (7) | 0.039 (8) | 0.096 (7) | 0.026 (6) | −0.017 (6) | −0.012 (6) |
C15 | 0.043 (7) | 0.047 (7) | 0.091 (7) | 0.025 (6) | 0.000 (6) | −0.008 (6) |
C16 | 0.048 (7) | 0.053 (7) | 0.092 (7) | 0.031 (6) | −0.007 (6) | −0.010 (6) |
C17 | 0.067 (8) | 0.056 (8) | 0.072 (6) | 0.027 (7) | 0.014 (6) | 0.013 (6) |
C18 | 0.036 (6) | 0.045 (6) | 0.090 (6) | 0.021 (6) | 0.006 (5) | 0.001 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.391 (16) | C7—C11 | 1.522 (15) |
O2—C10 | 1.388 (12) | C7—C18 | 1.543 (14) |
O2—C9 | 1.479 (16) | C8—C9 | 1.519 (17) |
C1—C2 | 1.387 (18) | C9—C17 | 1.544 (14) |
C1—C6 | 1.386 (19) | C9—C16 | 1.511 (18) |
C2—C3 | 1.394 (16) | C10—C11 | 1.387 (13) |
C3—C4 | 1.411 (18) | C10—C15 | 1.401 (18) |
C4—C5 | 1.395 (17) | C11—C12 | 1.391 (16) |
C4—C7 | 1.554 (13) | C12—C13 | 1.38 (2) |
C5—C6 | 1.385 (16) | C13—C14 | 1.387 (15) |
C7—C8 | 1.555 (12) | C14—C15 | 1.394 (17) |
| | | |
O1···O1i | 2.92 (2) | O1···O1ii | 2.92 (2) |
| | | |
C9—O2—C10 | 117.3 (7) | C7—C8—C9 | 115.8 (9) |
O1—C1—C2 | 123.0 (13) | O2—C9—C17 | 103.8 (8) |
C2—C1—C6 | 119.2 (11) | C8—C9—C16 | 116.1 (8) |
O1—C1—C6 | 117.7 (12) | C8—C9—C17 | 109.1 (10) |
C1—C2—C3 | 119.5 (12) | C16—C9—C17 | 111.1 (10) |
C2—C3—C4 | 122.4 (12) | O2—C9—C8 | 107.7 (10) |
C3—C4—C7 | 120.2 (9) | O2—C9—C16 | 108.2 (10) |
C5—C4—C7 | 123.7 (10) | O2—C10—C15 | 112.7 (8) |
C3—C4—C5 | 116.2 (9) | O2—C10—C11 | 124.6 (10) |
C4—C5—C6 | 121.8 (12) | C11—C10—C15 | 122.6 (10) |
C1—C6—C5 | 121.0 (12) | C10—C11—C12 | 116.5 (11) |
C4—C7—C18 | 108.1 (7) | C7—C11—C10 | 121.9 (9) |
C8—C7—C11 | 107.6 (7) | C7—C11—C12 | 121.6 (9) |
C4—C7—C11 | 111.1 (8) | C11—C12—C13 | 122.4 (10) |
C11—C7—C18 | 109.9 (9) | C12—C13—C14 | 120.4 (11) |
C8—C7—C18 | 107.8 (8) | C13—C14—C15 | 119.1 (13) |
C4—C7—C8 | 112.3 (8) | C10—C15—C14 | 119.0 (10) |
| | | |
C10—O2—C9—C8 | 42.3 (11) | C4—C7—C11—C10 | 109.3 (11) |
C10—O2—C9—C16 | −84.0 (10) | C4—C7—C11—C12 | −74.0 (13) |
C10—O2—C9—C17 | 157.9 (9) | C8—C7—C11—C10 | −14.0 (14) |
C9—O2—C10—C11 | −15.3 (15) | C8—C7—C11—C12 | 162.7 (11) |
C9—O2—C10—C15 | 167.2 (10) | C18—C7—C11—C10 | −131.1 (11) |
O1—C1—C2—C3 | −177.7 (11) | C11—C7—C8—C9 | 44.1 (12) |
C2—C1—C6—C5 | 1.8 (18) | C18—C7—C8—C9 | 162.5 (9) |
C6—C1—C2—C3 | −1.4 (17) | C18—C7—C11—C12 | 45.6 (13) |
O1—C1—C6—C5 | 178.2 (11) | C7—C8—C9—C17 | −170.9 (9) |
C1—C2—C3—C4 | 0.9 (17) | C7—C8—C9—C16 | 62.7 (14) |
C2—C3—C4—C5 | −0.7 (16) | C7—C8—C9—O2 | −58.8 (10) |
C2—C3—C4—C7 | 178.7 (10) | O2—C10—C11—C7 | 0.1 (18) |
C3—C4—C5—C6 | 1.1 (16) | C15—C10—C11—C12 | 0.5 (17) |
C3—C4—C7—C11 | 179.8 (9) | O2—C10—C11—C12 | −176.7 (10) |
C3—C4—C7—C18 | 59.2 (12) | C15—C10—C11—C7 | 177.4 (10) |
C5—C4—C7—C8 | 119.7 (11) | C11—C10—C15—C14 | 0.8 (18) |
C5—C4—C7—C11 | −0.8 (13) | O2—C10—C15—C14 | 178.4 (10) |
C5—C4—C7—C18 | −121.5 (11) | C10—C11—C12—C13 | −0.8 (18) |
C3—C4—C7—C8 | −59.7 (12) | C7—C11—C12—C13 | −177.7 (11) |
C7—C4—C5—C6 | −178.3 (10) | C11—C12—C13—C14 | 0 (2) |
C4—C5—C6—C1 | −1.6 (17) | C12—C13—C14—C15 | 1.6 (19) |
C4—C7—C8—C9 | −78.4 (11) | C13—C14—C15—C10 | −1.9 (18) |
Symmetry codes: (i) y, −x+y, −z; (ii) x−y, x, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1i | 0.67 (9) | 2.31 (9) | 2.92 (2) | 153 (9) |
Symmetry code: (i) y, −x+y, −z. |