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In the molecular structure of the title compound, C21H44O2, the hydrocarbon skeleton has an all-trans conformation. One of the terminal hydroxyl groups is also trans with respect to the skeleton, while the other is gauche. In the crystal structure, the molecules lie parallel to the b axis, forming layers with a thickness of b/2. The packing is similar to that in the smectic A phase of liquid crystals. These features are similar to those of the homologues with an odd number of C atoms, but different from those with an even number.
Supporting information
CCDC reference: 153917
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
C21H44O2 | Dx = 1.029 Mg m−3 |
Mr = 328.58 | Cu Kα radiation, λ = 1.5418 Å |
Orthorhombic, P212121 | Cell parameters from 24 reflections |
a = 7.247 (4) Å | θ = 9.2–13.9° |
b = 57.940 (3) Å | µ = 0.48 mm−1 |
c = 5.048 (4) Å | T = 296 K |
V = 2119 (1) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.50 × 0.05 mm |
F(000) = 744 | |
Data collection top
Rigaku AFC-5R diffractometer | 1583 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.022 |
Graphite monochromator | θmax = 70.6°, θmin = 3.1° |
ω scans | h = −2→8 |
Absorption correction: ψ scans (North et al., 1968) | k = 0→70 |
Tmin = 0.825, Tmax = 0.999 | l = −1→6 |
3723 measured reflections | 3 standard reflections every 150 reflections |
2355 independent reflections | intensity decay: 4% |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo) + 0.00106|Fo|2] |
S = 1.67 | (Δ/σ)max < 0.001 |
1583 reflections | Δρmax = 0.11 e Å−3 |
208 parameters | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. none |
Geometry. none # O···O details from PLATON (Spek, 1998) # O1···O2i 2.778 (5) Å i =
-5/2 - x,-y,1/2 + z # O2···O1ii 2.717 (4) Å ii= -2 -
x,1/2 + y,-3/2 - z |
Refinement. None |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −1.0589 (4) | −0.23208 (3) | −0.6415 (4) | 0.0747 (6) | |
O2 | −1.0627 (4) | 0.22760 (3) | −1.0705 (5) | 0.0836 (7) | |
C1 | −0.9982 (6) | −0.22978 (4) | −0.9085 (7) | 0.083 (1) | |
C2 | −1.0545 (6) | −0.20709 (4) | −1.0268 (6) | 0.0715 (9) | |
C3 | −0.9661 (5) | −0.18604 (4) | −0.8983 (6) | 0.0595 (8) | |
C4 | −1.0384 (5) | −0.16364 (4) | −1.0119 (6) | 0.0584 (8) | |
C5 | −0.9575 (5) | −0.14210 (4) | −0.8880 (6) | 0.0549 (7) | |
C6 | −1.0361 (5) | −0.11986 (4) | −0.9999 (6) | 0.0559 (8) | |
C7 | −0.9568 (5) | −0.09813 (4) | −0.8779 (6) | 0.0553 (7) | |
C8 | −1.0377 (5) | −0.07600 (4) | −0.9907 (6) | 0.0550 (7) | |
C9 | −0.9586 (4) | −0.05416 (4) | −0.8718 (6) | 0.0537 (7) | |
C10 | −1.0396 (5) | −0.03217 (4) | −0.9865 (6) | 0.0558 (7) | |
C11 | −0.9597 (4) | −0.01026 (4) | −0.8692 (6) | 0.0546 (7) | |
C12 | −1.0395 (4) | 0.01170 (4) | −0.9854 (6) | 0.0541 (7) | |
C13 | −0.9600 (4) | 0.03370 (4) | −0.8694 (6) | 0.0550 (7) | |
C14 | −1.0403 (5) | 0.05562 (4) | −0.9876 (6) | 0.0548 (7) | |
C15 | −0.9608 (5) | 0.07764 (4) | −0.8736 (6) | 0.0555 (7) | |
C16 | −1.0401 (5) | 0.09944 (4) | −0.9947 (6) | 0.0545 (7) | |
C17 | −0.9596 (5) | 0.12167 (4) | −0.8839 (6) | 0.0556 (7) | |
C18 | −1.0404 (5) | 0.14326 (4) | −1.0082 (6) | 0.0564 (7) | |
C19 | −0.9612 (5) | 0.16574 (4) | −0.9042 (6) | 0.0574 (8) | |
C20 | −1.0465 (5) | 0.18680 (4) | −1.0349 (6) | 0.0598 (8) | |
C21 | −0.9723 (5) | 0.20936 (4) | −0.9359 (6) | 0.0653 (9) | |
H1A | −0.8715 | −0.2311 | −0.9209 | 0.0903* | |
H1B | −1.0560 | −0.2417 | −1.0173 | 0.0903* | |
H1O | −1.1937 | −0.2308 | −0.6318 | 0.0898* | |
H2A | −1.0255 | −0.2070 | −1.2098 | 0.0847* | |
H2B | −1.1875 | −0.2056 | −1.0095 | 0.0847* | |
H2O | −1.0137 | 0.2420 | −1.0100 | 0.0948* | |
H3A | −0.9945 | −0.1862 | −0.7134 | 0.0679* | |
H3B | −0.8387 | −0.1867 | −0.9240 | 0.0679* | |
H4A | −1.0101 | −0.1634 | −1.1957 | 0.0701* | |
H4B | −1.1693 | −0.1633 | −0.9902 | 0.0701* | |
H5A | −0.9851 | −0.1424 | −0.7020 | 0.0648* | |
H5B | −0.8296 | −0.1420 | −0.9131 | 0.0648* | |
H6A | −1.0114 | −0.1196 | −1.1843 | 0.0675* | |
H6B | −1.1669 | −0.1199 | −0.9732 | 0.0675* | |
H7A | −0.9847 | −0.0984 | −0.6920 | 0.0650* | |
H7B | −0.8291 | −0.0980 | −0.9031 | 0.0650* | |
H8A | −1.0115 | −0.0758 | −1.1750 | 0.0648* | |
H8B | −1.1667 | −0.0761 | −0.9634 | 0.0648* | |
H9A | −0.9861 | −0.0542 | −0.6867 | 0.0631* | |
H9B | −0.8310 | −0.0539 | −0.8985 | 0.0631* | |
H10A | −1.0156 | −0.0320 | −1.1708 | 0.0658* | |
H10B | −1.1689 | −0.0321 | −0.9565 | 0.0658* | |
H11A | −0.9855 | −0.0101 | −0.6835 | 0.0644* | |
H11B | −0.8311 | −0.0102 | −0.8962 | 0.0644* | |
H12A | −1.0141 | 0.0117 | −1.1698 | 0.0628* | |
H12B | −1.1682 | 0.0117 | −0.9566 | 0.0628* | |
H13A | −0.9843 | 0.0338 | −0.6832 | 0.0658* | |
H13B | −0.8302 | 0.0337 | −0.8965 | 0.0658* | |
H14A | −1.0151 | 0.0555 | −1.1716 | 0.0639* | |
H14B | −1.1684 | 0.0556 | −0.9573 | 0.0639* | |
H15A | −0.9851 | 0.0780 | −0.6874 | 0.0663* | |
H15B | −0.8304 | 0.0777 | −0.8998 | 0.0663* | |
H16A | −1.0151 | 0.0991 | −1.1790 | 0.0642* | |
H16B | −1.1683 | 0.0996 | −0.9644 | 0.0642* | |
H17A | −0.9824 | 0.1223 | −0.6969 | 0.0666* | |
H17B | −0.8287 | 0.1218 | −0.9107 | 0.0666* | |
H18A | −1.0158 | 0.1426 | −1.1934 | 0.0654* | |
H18B | −1.1685 | 0.1433 | −0.9783 | 0.0654* | |
H19A | −0.9837 | 0.1666 | −0.7168 | 0.0704* | |
H19B | −0.8309 | 0.1660 | −0.9318 | 0.0704* | |
H20A | −1.0242 | 0.1857 | −1.2213 | 0.0706* | |
H20B | −1.1756 | 0.1865 | −1.0043 | 0.0706* | |
H21A | −0.8405 | 0.2101 | −0.9723 | 0.0802* | |
H21B | −0.9891 | 0.2107 | −0.7512 | 0.0802* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.110 (2) | 0.0454 (8) | 0.068 (1) | 0.005 (1) | 0.005 (2) | 0.0058 (9) |
O2 | 0.114 (2) | 0.0375 (8) | 0.099 (2) | −0.002 (1) | −0.026 (2) | 0.0017 (9) |
C1 | 0.138 (4) | 0.042 (1) | 0.070 (2) | 0.002 (2) | 0.012 (2) | −0.008 (1) |
C2 | 0.113 (3) | 0.046 (1) | 0.056 (1) | −0.005 (2) | −0.004 (2) | −0.002 (1) |
C3 | 0.080 (2) | 0.040 (1) | 0.059 (1) | −0.001 (1) | 0.001 (2) | 0.000 (1) |
C4 | 0.077 (2) | 0.042 (1) | 0.056 (1) | 0.000 (1) | −0.003 (2) | 0.003 (1) |
C5 | 0.064 (2) | 0.040 (1) | 0.061 (1) | −0.001 (1) | 0.000 (2) | 0.001 (1) |
C6 | 0.068 (2) | 0.041 (1) | 0.059 (1) | 0.000 (1) | −0.001 (2) | 0.003 (1) |
C7 | 0.067 (2) | 0.039 (1) | 0.060 (1) | −0.002 (1) | 0.000 (2) | 0.001 (1) |
C8 | 0.065 (2) | 0.040 (1) | 0.060 (1) | 0.001 (1) | −0.003 (2) | 0.003 (1) |
C9 | 0.062 (2) | 0.039 (1) | 0.060 (1) | −0.002 (1) | −0.002 (2) | 0.002 (1) |
C10 | 0.068 (2) | 0.039 (1) | 0.061 (1) | 0.001 (1) | −0.002 (2) | 0.002 (1) |
C11 | 0.064 (2) | 0.039 (1) | 0.061 (1) | −0.002 (1) | −0.002 (2) | 0.001 (1) |
C12 | 0.064 (2) | 0.038 (1) | 0.060 (1) | 0.001 (1) | −0.003 (2) | 0.001 (1) |
C13 | 0.065 (2) | 0.040 (1) | 0.061 (1) | −0.002 (1) | −0.001 (2) | 0.001 (1) |
C14 | 0.065 (2) | 0.038 (1) | 0.060 (1) | 0.000 (1) | 0.000 (2) | 0.001 (1) |
C15 | 0.066 (2) | 0.039 (1) | 0.061 (1) | −0.001 (1) | −0.002 (2) | −0.001 (1) |
C16 | 0.064 (2) | 0.040 (1) | 0.060 (2) | 0.001 (1) | −0.002 (2) | −0.002 (1) |
C17 | 0.067 (2) | 0.040 (1) | 0.060 (1) | 0.000 (1) | −0.003 (2) | −0.003 (1) |
C18 | 0.069 (2) | 0.039 (1) | 0.061 (1) | 0.003 (1) | −0.003 (2) | −0.001 (1) |
C19 | 0.069 (2) | 0.041 (1) | 0.062 (2) | 0.000 (1) | −0.003 (2) | −0.003 (1) |
C20 | 0.073 (2) | 0.040 (1) | 0.067 (2) | 0.001 (1) | −0.002 (2) | −0.001 (1) |
C21 | 0.082 (3) | 0.039 (1) | 0.075 (2) | 0.002 (1) | −0.001 (2) | 0.000 (1) |
Geometric parameters (Å, º) top
O1—C1 | 1.424 (4) | C10—C11 | 1.516 (4) |
O2—C21 | 1.417 (3) | C11—C12 | 1.516 (3) |
C1—C2 | 1.501 (4) | C12—C13 | 1.516 (3) |
C2—C3 | 1.523 (4) | C13—C14 | 1.519 (3) |
C3—C4 | 1.513 (3) | C14—C15 | 1.513 (3) |
C4—C5 | 1.514 (4) | C15—C16 | 1.516 (3) |
C5—C6 | 1.518 (3) | C16—C17 | 1.520 (3) |
C6—C7 | 1.515 (3) | C17—C18 | 1.517 (3) |
C7—C8 | 1.521 (3) | C18—C19 | 1.517 (3) |
C8—C9 | 1.513 (3) | C19—C20 | 1.519 (4) |
C9—C10 | 1.518 (3) | C20—C21 | 1.499 (3) |
| | | |
O1—C1—C2 | 112.0 (3) | C11—C12—C13 | 114.2 (2) |
C1—C2—C3 | 114.7 (3) | C12—C13—C14 | 113.9 (2) |
C2—C3—C4 | 112.3 (3) | C13—C14—C15 | 114.2 (3) |
C3—C4—C5 | 114.6 (3) | C14—C15—C16 | 113.9 (3) |
C4—C5—C6 | 113.6 (3) | C15—C16—C17 | 114.3 (3) |
C5—C6—C7 | 114.3 (3) | C16—C17—C18 | 113.5 (3) |
C6—C7—C8 | 113.7 (3) | C17—C18—C19 | 114.8 (3) |
C7—C8—C9 | 114.2 (3) | C18—C19—C20 | 112.7 (3) |
C8—C9—C10 | 113.8 (3) | C19—C20—C21 | 114.2 (3) |
C9—C10—C11 | 113.9 (2) | O2—C21—C20 | 108.9 (3) |
C10—C11—C12 | 113.9 (2) | | |
| | | |
O1—C1—C2—C3 | 65.1 (5) | O2—C21—C20—C19 | −179.6 (3) |
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