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In the title compound, C15H32O2, one of the terminal hydroxyl groups has a gauche conformation with respect to the hydro­carbon skeleton, while the other is trans. The mol­ecules lie parallel to the longest axis and form layers similar to those of the smectic A structure 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006272/de1141sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006272/de1141Isup2.hkl
Contains datablock I

CCDC reference: 147678

Comment top

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.

Experimental top

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).

Refinement top

All H atoms including hydroxyl H atoms were fixed in idealized positions.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. An ORTEPII (Johnson, 1976) view of the title molecule showing the crystallographic numbering scheme. Displacement ellipsoids are drawn at 50% probability level.
[Figure 2] Fig. 2. The projection of the crystal structure along c axis. Dotted lines indicate the hydrogen bond.
(I) top
Crystal data top
C15H32O2F(000) = 552.00
Mr = 244.42Dx = 1.041 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 7.177 (2) Åθ = 35.4–38.9°
b = 42.670 (2) ŵ = 0.51 mm1
c = 5.090 (2) ÅT = 296 K
V = 1559.0 (8) Å3Plate, colorless
Z = 40.6 × 0.3 × 0.03 mm
Data collection top
Rigaku AFC5R
diffractometer
1165 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.029
Graphite monochromatorθmax = 70.6°, θmin = 3.1°
ω–2θ scansh = 28
Absorption correction: ψ scans
(North et al., 1968)
k = 052
Tmin = 0.917, Tmax = 0.999l = 16
2756 measured reflections3 standard reflections every 150 reflections
1734 independent reflections intensity decay: 8.8%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.049H-atom parameters not refined
wR(F2) = 0.058w = 1/[σ2(Fo) + 0.00063|Fo|2]
S = 1.39(Δ/σ)max = 0.0004
1165 reflectionsΔρmax = 0.14 e Å3
154 parametersΔρmin = 0.32 e Å3
Crystal data top
C15H32O2V = 1559.0 (8) Å3
Mr = 244.42Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.177 (2) ŵ = 0.51 mm1
b = 42.670 (2) ÅT = 296 K
c = 5.090 (2) Å0.6 × 0.3 × 0.03 mm
Data collection top
Rigaku AFC5R
diffractometer
1165 reflections with I > 2σ(I)
Absorption correction: ψ scans
(North et al., 1968)
Rint = 0.029
Tmin = 0.917, Tmax = 0.9993 standard reflections every 150 reflections
2756 measured reflections intensity decay: 8.8%
1734 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.058H-atom parameters not refined
S = 1.39Δρmax = 0.14 e Å3
1165 reflectionsΔρmin = 0.32 e Å3
154 parameters
Special details top

Experimental. none

Geometry. none

Refinement. None

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0512 (3)0.22520 (4)0.1427 (4)0.0606 (6)
O20.0664 (3)0.22004 (4)0.5714 (4)0.0695 (6)
C10.0060 (5)0.22223 (6)0.4089 (6)0.0626 (9)
C20.0504 (5)0.19158 (6)0.5280 (6)0.0568 (8)
C30.0357 (4)0.16284 (5)0.4024 (5)0.0476 (7)
C40.0368 (4)0.13240 (5)0.5153 (5)0.0476 (7)
C50.0433 (4)0.10311 (5)0.3926 (5)0.0465 (7)
C60.0365 (4)0.07296 (5)0.5044 (5)0.0466 (7)
C70.0420 (4)0.04327 (5)0.3837 (6)0.0468 (7)
C80.0387 (4)0.01350 (6)0.4976 (5)0.0457 (6)
C90.0410 (4)0.01640 (5)0.3817 (5)0.0463 (6)
C100.0395 (4)0.04607 (5)0.4997 (5)0.0454 (7)
C110.0407 (4)0.07614 (5)0.3889 (6)0.0469 (7)
C120.0410 (4)0.10549 (5)0.5116 (6)0.0467 (7)
C130.0379 (4)0.13611 (5)0.4082 (5)0.0464 (7)
C140.0478 (4)0.16465 (5)0.5374 (6)0.0495 (7)
C150.0265 (4)0.19535 (5)0.4382 (6)0.0534 (8)
H1a0.13580.22400.41900.0758*
H1b0.05010.23890.51110.0758*
H1o0.18710.22380.13280.0721*
H2a0.02280.19150.71010.0657*
H2b0.18590.18950.51080.0657*
H2o0.02230.23990.51270.0770*
H3a0.01250.16300.21670.0573*
H3b0.16800.16360.42830.0573*
H4a0.01120.13190.69870.0568*
H4b0.16960.13180.49130.0568*
H5a0.02090.10350.20800.0545*
H5b0.17510.10290.42150.0545*
H6a0.01520.07250.68810.0561*
H6b0.16850.07300.47340.0561*
H7a0.02070.04370.20110.0551*
H7b0.17350.04320.41650.0551*
H8a0.01960.01340.68110.0545*
H8b0.16980.01350.46200.0545*
H9a0.02150.01660.19920.0547*
H9b0.17240.01670.41720.0547*
H10a0.02280.04600.68350.0545*
H10b0.17140.04640.46220.0545*
H11a0.02320.07700.20450.0566*
H11b0.17320.07640.42380.0566*
H12a0.02360.10460.69640.0558*
H12b0.17340.10530.47680.0558*
H13a0.01730.13740.22230.0565*
H13b0.16940.13640.43860.0565*
H14a0.02840.16310.72340.0587*
H14b0.18040.16410.50700.0587*
H15a0.15980.19670.47390.0646*
H15b0.01090.19720.25310.0646*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.083 (1)0.0398 (9)0.059 (1)0.0062 (10)0.003 (1)0.0059 (9)
O20.089 (1)0.0340 (8)0.086 (2)0.0033 (10)0.025 (2)0.0008 (9)
C10.085 (2)0.038 (1)0.066 (2)0.003 (1)0.006 (2)0.009 (1)
C20.081 (2)0.044 (1)0.045 (1)0.004 (1)0.005 (2)0.004 (1)
C30.057 (2)0.037 (1)0.050 (1)0.002 (1)0.002 (2)0.000 (1)
C40.053 (2)0.039 (1)0.050 (1)0.000 (1)0.003 (2)0.004 (1)
C50.051 (2)0.036 (1)0.053 (1)0.002 (1)0.000 (2)0.003 (1)
C60.049 (2)0.037 (1)0.053 (2)0.001 (1)0.000 (2)0.005 (1)
C70.049 (2)0.036 (1)0.055 (1)0.000 (1)0.003 (2)0.001 (1)
C80.048 (1)0.037 (1)0.052 (1)0.000 (1)0.000 (1)0.003 (1)
C90.049 (1)0.038 (1)0.053 (1)0.002 (1)0.004 (2)0.001 (1)
C100.048 (1)0.036 (1)0.052 (1)0.001 (1)0.006 (2)0.002 (1)
C110.049 (2)0.038 (1)0.054 (1)0.000 (1)0.004 (2)0.001 (1)
C120.049 (1)0.035 (1)0.056 (1)0.001 (1)0.002 (2)0.000 (1)
C130.049 (2)0.038 (1)0.053 (2)0.001 (1)0.002 (2)0.002 (1)
C140.054 (2)0.037 (1)0.058 (2)0.001 (1)0.000 (2)0.003 (1)
C150.059 (2)0.037 (1)0.064 (2)0.002 (1)0.003 (2)0.000 (1)
Geometric parameters (Å, º) top
O1—C11.422 (4)C7—C81.512 (3)
O2—C151.419 (3)C8—C91.517 (3)
C1—C21.497 (4)C9—C101.516 (3)
C2—C31.515 (3)C10—C111.515 (3)
C3—C41.513 (3)C11—C121.517 (3)
C4—C51.511 (3)C12—C131.519 (3)
C5—C61.519 (3)C13—C141.514 (3)
C6—C71.516 (3)C14—C151.502 (3)
O1—C1—C2112.7 (2)C8—C9—C10113.8 (2)
C1—C2—C3115.2 (3)C9—C10—C11114.5 (2)
C2—C3—C4113.2 (2)C10—C11—C12113.5 (2)
C3—C4—C5115.0 (2)C11—C12—C13115.0 (2)
C4—C5—C6113.7 (2)C12—C13—C14112.9 (2)
C5—C6—C7114.6 (2)C13—C14—C15114.3 (2)
C6—C7—C8113.8 (2)O2—C15—C14108.6 (2)
C7—C8—C9114.4 (2)
O1—C1—C2—C363.2 (4)O2—C15—C14—C13179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O1i0.951.772.713 (2)172
O1—H1o···O2ii0.981.802.777 (3)173
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x1/2, y, z1/2.

Experimental details

Crystal data
Chemical formulaC15H32O2
Mr244.42
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)7.177 (2), 42.670 (2), 5.090 (2)
V3)1559.0 (8)
Z4
Radiation typeCu Kα
µ (mm1)0.51
Crystal size (mm)0.6 × 0.3 × 0.03
Data collection
DiffractometerRigaku AFC5R
diffractometer
Absorption correctionψ scans
(North et al., 1968)
Tmin, Tmax0.917, 0.999
No. of measured, independent and
observed [I > 2σ(I)] reflections
2756, 1734, 1165
Rint0.029
(sin θ/λ)max1)0.612
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.058, 1.39
No. of reflections1165
No. of parameters154
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)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.

Selected geometric parameters (Å, º) top
O1—C11.422 (4)C7—C81.512 (3)
O2—C151.419 (3)C8—C91.517 (3)
C1—C21.497 (4)C9—C101.516 (3)
C2—C31.515 (3)C10—C111.515 (3)
C3—C41.513 (3)C11—C121.517 (3)
C4—C51.511 (3)C12—C131.519 (3)
C5—C61.519 (3)C13—C141.514 (3)
C6—C71.516 (3)C14—C151.502 (3)
O1—C1—C2112.7 (2)C8—C9—C10113.8 (2)
C1—C2—C3115.2 (3)C9—C10—C11114.5 (2)
C2—C3—C4113.2 (2)C10—C11—C12113.5 (2)
C3—C4—C5115.0 (2)C11—C12—C13115.0 (2)
C4—C5—C6113.7 (2)C12—C13—C14112.9 (2)
C5—C6—C7114.6 (2)C13—C14—C15114.3 (2)
C6—C7—C8113.8 (2)O2—C15—C14108.6 (2)
C7—C8—C9114.4 (2)
O1—C1—C2—C363.2 (4)O2—C15—C14—C13179.2 (2)
 

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