Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006272/de1141sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006272/de1141Isup2.hkl |
CCDC reference: 147678
According to the conventional method, the title compound was synthesized from commercially available pentadecanedioic acid (Tokyo Kasei Kogyo Co., Ltd.) by esterification and reduction with LiAlH4. The single-crystal used for analysis was grown by very slow evaporation from a solution with a mixed solvent of methanol, ethyl acetate and n-heptane (1:1:3).
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
C15H32O2 | F(000) = 552.00 |
Mr = 244.42 | Dx = 1.041 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 7.177 (2) Å | θ = 35.4–38.9° |
b = 42.670 (2) Å | µ = 0.51 mm−1 |
c = 5.090 (2) Å | T = 296 K |
V = 1559.0 (8) Å3 | Plate, colorless |
Z = 4 | 0.6 × 0.3 × 0.03 mm |
Rigaku AFC5R diffractometer | 1165 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.029 |
Graphite monochromator | θmax = 70.6°, θmin = 3.1° |
ω–2θ scans | h = −2→8 |
Absorption correction: ψ scans (North et al., 1968) | k = 0→52 |
Tmin = 0.917, Tmax = 0.999 | l = −1→6 |
2756 measured reflections | 3 standard reflections every 150 reflections |
1734 independent reflections | intensity decay: 8.8% |
Refinement on F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters not refined |
wR(F2) = 0.058 | w = 1/[σ2(Fo) + 0.00063|Fo|2] |
S = 1.39 | (Δ/σ)max = 0.0004 |
1165 reflections | Δρmax = 0.14 e Å−3 |
154 parameters | Δρmin = −0.32 e Å−3 |
C15H32O2 | V = 1559.0 (8) Å3 |
Mr = 244.42 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.177 (2) Å | µ = 0.51 mm−1 |
b = 42.670 (2) Å | T = 296 K |
c = 5.090 (2) Å | 0.6 × 0.3 × 0.03 mm |
Rigaku AFC5R diffractometer | 1165 reflections with I > 2σ(I) |
Absorption correction: ψ scans (North et al., 1968) | Rint = 0.029 |
Tmin = 0.917, Tmax = 0.999 | 3 standard reflections every 150 reflections |
2756 measured reflections | intensity decay: 8.8% |
1734 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.058 | H-atom parameters not refined |
S = 1.39 | Δρmax = 0.14 e Å−3 |
1165 reflections | Δρmin = −0.32 e Å−3 |
154 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0512 (3) | 0.22520 (4) | 0.1427 (4) | 0.0606 (6) | |
O2 | −0.0664 (3) | −0.22004 (4) | 0.5714 (4) | 0.0695 (6) | |
C1 | 0.0060 (5) | 0.22223 (6) | 0.4089 (6) | 0.0626 (9) | |
C2 | −0.0504 (5) | 0.19158 (6) | 0.5280 (6) | 0.0568 (8) | |
C3 | 0.0357 (4) | 0.16284 (5) | 0.4024 (5) | 0.0476 (7) | |
C4 | −0.0368 (4) | 0.13240 (5) | 0.5153 (5) | 0.0476 (7) | |
C5 | 0.0433 (4) | 0.10311 (5) | 0.3926 (5) | 0.0465 (7) | |
C6 | −0.0365 (4) | 0.07296 (5) | 0.5044 (5) | 0.0466 (7) | |
C7 | 0.0420 (4) | 0.04327 (5) | 0.3837 (6) | 0.0468 (7) | |
C8 | −0.0387 (4) | 0.01350 (6) | 0.4976 (5) | 0.0457 (6) | |
C9 | 0.0410 (4) | −0.01640 (5) | 0.3817 (5) | 0.0463 (6) | |
C10 | −0.0395 (4) | −0.04607 (5) | 0.4997 (5) | 0.0454 (7) | |
C11 | 0.0407 (4) | −0.07614 (5) | 0.3889 (6) | 0.0469 (7) | |
C12 | −0.0410 (4) | −0.10549 (5) | 0.5116 (6) | 0.0467 (7) | |
C13 | 0.0379 (4) | −0.13611 (5) | 0.4082 (5) | 0.0464 (7) | |
C14 | −0.0478 (4) | −0.16465 (5) | 0.5374 (6) | 0.0495 (7) | |
C15 | 0.0265 (4) | −0.19535 (5) | 0.4382 (6) | 0.0534 (8) | |
H1a | 0.1358 | 0.2240 | 0.4190 | 0.0758* | |
H1b | −0.0501 | 0.2389 | 0.5111 | 0.0758* | |
H1o | −0.1871 | 0.2238 | 0.1328 | 0.0721* | |
H2a | −0.0228 | 0.1915 | 0.7101 | 0.0657* | |
H2b | −0.1859 | 0.1895 | 0.5108 | 0.0657* | |
H2o | −0.0223 | −0.2399 | 0.5127 | 0.0770* | |
H3a | 0.0125 | 0.1630 | 0.2167 | 0.0573* | |
H3b | 0.1680 | 0.1636 | 0.4283 | 0.0573* | |
H4a | −0.0112 | 0.1319 | 0.6987 | 0.0568* | |
H4b | −0.1696 | 0.1318 | 0.4913 | 0.0568* | |
H5a | 0.0209 | 0.1035 | 0.2080 | 0.0545* | |
H5b | 0.1751 | 0.1029 | 0.4215 | 0.0545* | |
H6a | −0.0152 | 0.0725 | 0.6881 | 0.0561* | |
H6b | −0.1685 | 0.0730 | 0.4734 | 0.0561* | |
H7a | 0.0207 | 0.0437 | 0.2011 | 0.0551* | |
H7b | 0.1735 | 0.0432 | 0.4165 | 0.0551* | |
H8a | −0.0196 | 0.0134 | 0.6811 | 0.0545* | |
H8b | −0.1698 | 0.0135 | 0.4620 | 0.0545* | |
H9a | 0.0215 | −0.0166 | 0.1992 | 0.0547* | |
H9b | 0.1724 | −0.0167 | 0.4172 | 0.0547* | |
H10a | −0.0228 | −0.0460 | 0.6835 | 0.0545* | |
H10b | −0.1714 | −0.0464 | 0.4622 | 0.0545* | |
H11a | 0.0232 | −0.0770 | 0.2045 | 0.0566* | |
H11b | 0.1732 | −0.0764 | 0.4238 | 0.0566* | |
H12a | −0.0236 | −0.1046 | 0.6964 | 0.0558* | |
H12b | −0.1734 | −0.1053 | 0.4768 | 0.0558* | |
H13a | 0.0173 | −0.1374 | 0.2223 | 0.0565* | |
H13b | 0.1694 | −0.1364 | 0.4386 | 0.0565* | |
H14a | −0.0284 | −0.1631 | 0.7234 | 0.0587* | |
H14b | −0.1804 | −0.1641 | 0.5070 | 0.0587* | |
H15a | 0.1598 | −0.1967 | 0.4739 | 0.0646* | |
H15b | 0.0109 | −0.1972 | 0.2531 | 0.0646* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.083 (1) | 0.0398 (9) | 0.059 (1) | −0.0062 (10) | −0.003 (1) | 0.0059 (9) |
O2 | 0.089 (1) | 0.0340 (8) | 0.086 (2) | 0.0033 (10) | 0.025 (2) | −0.0008 (9) |
C1 | 0.085 (2) | 0.038 (1) | 0.066 (2) | −0.003 (1) | −0.006 (2) | −0.009 (1) |
C2 | 0.081 (2) | 0.044 (1) | 0.045 (1) | 0.004 (1) | 0.005 (2) | −0.004 (1) |
C3 | 0.057 (2) | 0.037 (1) | 0.050 (1) | 0.002 (1) | 0.002 (2) | 0.000 (1) |
C4 | 0.053 (2) | 0.039 (1) | 0.050 (1) | 0.000 (1) | 0.003 (2) | 0.004 (1) |
C5 | 0.051 (2) | 0.036 (1) | 0.053 (1) | 0.002 (1) | 0.000 (2) | 0.003 (1) |
C6 | 0.049 (2) | 0.037 (1) | 0.053 (2) | 0.001 (1) | 0.000 (2) | 0.005 (1) |
C7 | 0.049 (2) | 0.036 (1) | 0.055 (1) | 0.000 (1) | 0.003 (2) | 0.001 (1) |
C8 | 0.048 (1) | 0.037 (1) | 0.052 (1) | 0.000 (1) | 0.000 (1) | 0.003 (1) |
C9 | 0.049 (1) | 0.038 (1) | 0.053 (1) | 0.002 (1) | 0.004 (2) | 0.001 (1) |
C10 | 0.048 (1) | 0.036 (1) | 0.052 (1) | −0.001 (1) | 0.006 (2) | 0.002 (1) |
C11 | 0.049 (2) | 0.038 (1) | 0.054 (1) | 0.000 (1) | 0.004 (2) | 0.001 (1) |
C12 | 0.049 (1) | 0.035 (1) | 0.056 (1) | 0.001 (1) | 0.002 (2) | 0.000 (1) |
C13 | 0.049 (2) | 0.038 (1) | 0.053 (2) | 0.001 (1) | 0.002 (2) | −0.002 (1) |
C14 | 0.054 (2) | 0.037 (1) | 0.058 (2) | 0.001 (1) | 0.000 (2) | −0.003 (1) |
C15 | 0.059 (2) | 0.037 (1) | 0.064 (2) | 0.002 (1) | 0.003 (2) | 0.000 (1) |
O1—C1 | 1.422 (4) | C7—C8 | 1.512 (3) |
O2—C15 | 1.419 (3) | C8—C9 | 1.517 (3) |
C1—C2 | 1.497 (4) | C9—C10 | 1.516 (3) |
C2—C3 | 1.515 (3) | C10—C11 | 1.515 (3) |
C3—C4 | 1.513 (3) | C11—C12 | 1.517 (3) |
C4—C5 | 1.511 (3) | C12—C13 | 1.519 (3) |
C5—C6 | 1.519 (3) | C13—C14 | 1.514 (3) |
C6—C7 | 1.516 (3) | C14—C15 | 1.502 (3) |
O1—C1—C2 | 112.7 (2) | C8—C9—C10 | 113.8 (2) |
C1—C2—C3 | 115.2 (3) | C9—C10—C11 | 114.5 (2) |
C2—C3—C4 | 113.2 (2) | C10—C11—C12 | 113.5 (2) |
C3—C4—C5 | 115.0 (2) | C11—C12—C13 | 115.0 (2) |
C4—C5—C6 | 113.7 (2) | C12—C13—C14 | 112.9 (2) |
C5—C6—C7 | 114.6 (2) | C13—C14—C15 | 114.3 (2) |
C6—C7—C8 | 113.8 (2) | O2—C15—C14 | 108.6 (2) |
C7—C8—C9 | 114.4 (2) | ||
O1—C1—C2—C3 | 63.2 (4) | O2—C15—C14—C13 | −179.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···O1i | 0.95 | 1.77 | 2.713 (2) | 172 |
O1—H1o···O2ii | 0.98 | 1.80 | 2.777 (3) | 173 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x−1/2, −y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H32O2 |
Mr | 244.42 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 7.177 (2), 42.670 (2), 5.090 (2) |
V (Å3) | 1559.0 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.51 |
Crystal size (mm) | 0.6 × 0.3 × 0.03 |
Data collection | |
Diffractometer | Rigaku AFC5R diffractometer |
Absorption correction | ψ scans (North et al., 1968) |
Tmin, Tmax | 0.917, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2756, 1734, 1165 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.612 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.058, 1.39 |
No. of reflections | 1165 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.14, −0.32 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SAPI91 (Fan, 1991), TEXSAN.
O1—C1 | 1.422 (4) | C7—C8 | 1.512 (3) |
O2—C15 | 1.419 (3) | C8—C9 | 1.517 (3) |
C1—C2 | 1.497 (4) | C9—C10 | 1.516 (3) |
C2—C3 | 1.515 (3) | C10—C11 | 1.515 (3) |
C3—C4 | 1.513 (3) | C11—C12 | 1.517 (3) |
C4—C5 | 1.511 (3) | C12—C13 | 1.519 (3) |
C5—C6 | 1.519 (3) | C13—C14 | 1.514 (3) |
C6—C7 | 1.516 (3) | C14—C15 | 1.502 (3) |
O1—C1—C2 | 112.7 (2) | C8—C9—C10 | 113.8 (2) |
C1—C2—C3 | 115.2 (3) | C9—C10—C11 | 114.5 (2) |
C2—C3—C4 | 113.2 (2) | C10—C11—C12 | 113.5 (2) |
C3—C4—C5 | 115.0 (2) | C11—C12—C13 | 115.0 (2) |
C4—C5—C6 | 113.7 (2) | C12—C13—C14 | 112.9 (2) |
C5—C6—C7 | 114.6 (2) | C13—C14—C15 | 114.3 (2) |
C6—C7—C8 | 113.8 (2) | O2—C15—C14 | 108.6 (2) |
C7—C8—C9 | 114.4 (2) | ||
O1—C1—C2—C3 | 63.2 (4) | O2—C15—C14—C13 | −179.2 (2) |
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Normal long-chain compounds have attracted attention as a basic model of polymers, as they have a very simple chemical structure whose molecular skeleton is a straight hydrocarbon chain. In addition, these compounds have a layer structure similar to the smectic one of liquid crystals, and could therefore be regarded as the model compound of liquid crystals. Many researchers have studied crystal structures of normal long-chain compounds, for example, n-alkanes (Müller, 1928), α-monosubstituted n-alkanes such as n-higher alcohols (e.g. Watanabe, 1961; Seto, 1962). Recently some of the present authors reported phase-transition phenomena of normal long-chain α,ω-alkanediols from C13 to C24 with another researcher (Ogawa & Nakamura, 1999). Crystal structures of six α,ω-alkanediols, 1,10-decanediol (Nakamura & Sato, 1999a), 1,11-undecanediol (Nakamura et al., 1999), 1,12-dodecanediol (Nakamura & Setodoi, 1997), 1,13-tridecanediol (Nakamura et al., 1997), 1,14-tetradecanediol (Nakamura & Sato, 1999b) and 1,16-hexadecanediol (Nakamura & Yamamoto, 1994) have also been reported.
The molecular structure of 1,15-pentadecanediol, (I), is shown in Fig. 1. Essential structural parameters and shape of the molecule are quite similar to those of other homologues with an odd number of C atoms already reported, except the lattice parameter of the b axis. The terminal C1—O1 bond is gauche conformation with respect to the skeleton [O1—C1—C2—C3 torsion angle is 63.2 (4)°], whereas the other terminal C15—O2 bond is trans [O2—C15—C14—C13 torsion angle is −179.2 (2)°]. The molecules lie parallel to the b axis making layers formed with a thickness of b/2. The molecules are arranged in an anti-parallel fashion along the a axis in these layers, as can be seen in Fig. 2. This packing is very similar to the smectic A structure of liquid crystals. In this structure, the molecules form two different types of hydrogen bond, that is interlayer and intralayer hydrogen bonds. These features are already found in the homologues with an odd number of C atoms. The interlayer and intralayer hydrogen-bond distances O1—O2 are 2.713 (2) and 2.777 (3) Å long, respectively. The values of the hydrogen-bond distance are in good agreement with those of 1,11-undecanediol [2.710 (2) and 2.775 (3) Å long] and 1,13-tridecanediol [2.713 (2) and 2.776 (4) Å long]. \sch
It was reported in our previous papers that the molecular and crystal structures of the homologues with an even number of C atoms (1,10-decanediol, 1,12-dodecanediol, 1,14-tetradecanediol and 1,16-hexadecanediol) are different from those of the homologues with an odd number of C atoms. The hydrocarbon skeleton had the all-trans conformation, and both terminal C—O bonds also showed the trans conformation. The centrosymmetric molecules are arranged in a zigzag manner to make a herringbone motif. The structure could be regarded as a model structure of the smectic C liquid crystals. 1,12-Dibromododecane (Kuple et al., 1981), 1,16-dibromohexadecane (Kobayashi et al., 1995) and 1,18-dibromooctadecane (Nakamura et al., 1993) also showed the herringbone motif. In these structures, only interlayer hydrogen bonds are formed.