organic compounds
1,3,5-Tri-p-tolylpentane-1,5-diol
aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bPostgraduate Research Department of Chemistry, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, cDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamilnadu, India, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: thiruvalluvar.a@gmail.com
In the title compound, C26H30O2, the central benzene ring forms dihedral angles of 14.85 (15) and 28.17 (14)° with the terminal benzene rings. The dihedral angle between the terminal benzene rings is 32.14 (13)°. The crystal packing exhibits two strong intermolecular O—H⋯O hydrogen bonds, forming directed four-membered co-operative rings. A region of disordered electron density, most probably disordered ethyl acetate solvent molecules, occupying voids of ca 519 Å3 for an electron count of 59, was treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during The structure was refined as an [absolute structure parameter = −0.3 (4)].
CCDC reference: 979742
Related literature
For the procedure adopted to reduce 1,3,5-tris(p-tolyl)pentane-1,5-dione, see: Paul et al. (2012). For a less green reported synthesis of the starting diketone, 1,3,5-tris(p-tolyl)pentane-1,5-dione, see: Yang et al. (2005). For applications of related compounds, see: Sundberg & Faergemann (2008). For the crystal structures of related compounds, see: Ha & Young (2009); Barrett et al. (2000). For details of the use of the SQUEEZE and CAVITY routines in PLATON, see: Spek (2009). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 and PLATON.
Supporting information
CCDC reference: 979742
10.1107/S160053681400018X/su2686sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400018X/su2686Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400018X/su2686Isup3.cdx
Supporting information file. DOI: 10.1107/S160053681400018X/su2686Isup4.cml
To a stirred solution of 1,3,5-tris(p-tolyl)pentane-1,5-dione (0.4 g, 1.0 mmol) in methanol, sodium borohydride (0.08 g, 2.2 mmol) was added in portions in ambient conditions. After the completion of the reaction, the mixture was poured onto crushed ice and filtered off. The organic layer was dried over anhydrous sodium sulfate. The diastereomeric mixtures were separated by
using a mixture of petroleum ether and ethyl acetate (80:20) as The isolated compound was recrystallized in ethyl acetate to obtain colourless plate-like crystal of the title compound in good yield [0.344 g; 86%].All H-atoms were positioned geometrically and allowed to ride on their parent atoms: O-H = 0.84 Å, C—H = 0.95, 0.99, 1.00 and 0.98 Å for CH(aromatic), CH2, CH and CH3 H atoms, respectively, with Uiso(H) = 1.5Ueq(C-methyl and O) and = 1.2Ueq(C) for other H atoms. The disordered solvent molecules occupy ca. 14.3% of the unit-cell volume. This region of disordered electron density, probably disordered ethyl acetate solvent molecules, was treated with the SQUEEZE routine in PLATON (Spek, 2009), and the solvent-free model was employed for the final refinement.
The synthesis of the title compound has been achieved by the sodium borohydride reduction of the corresponding 1,5-diketone by a method reported recently (Paul et al. 2012). The starting diketone, 1,3,5-tris-(p-tolyl)pentane-1,5-dione, was prepared by a greener route slightly deviating from the reported one (Yang et al. 2005). Though, the separation of the diastereomeric mixture posed problems, it was possible to get one diastereomer in pure form. This acyclic pentane-1,5-diol can be employed for the generation of
like tetrahydropyran. Generally, pentane-1,5-diol derivatives are found to be more valuable than several other diols in connection with drug delivery-enhancing potency, pharmaceutical and cosmetic properties, antimicrobial spectrum and toxicity (Sundberg & Faergemann, 2008). The related compounds whose structures have been solved by X-ray are 2,2,3,3,4,4-hexafluoropentane-1,5-diol (Ha et al. 2009) and 3-methylenepentane-1,5-diols (Barrett et al. 2000).In the title molecule, Fig. 1, the pentane-1,5-diol unit (C1—C5/O1/O5) forms a regular zigzag pattern with torsion angles C1—C2—C3—C4 = 178.8 (2)° and C2—C3—C4—C5 = -177.4 (2)°, with the two diol groups pointing in opposite directions. The central benzene ring (C31-C36) forms dihedral angles of 14.85 (15) and 28.17 (14)° with the two terminal benzene rings (C11-C16 and C51-C56, respectively). The dihedral angle between the two terminal benzene rings is 32.14 (13)°. The C—C, Car—Car and C—O bond lengths are within their normal ranges (Allen et al., 1987).
In the crystal, there are two strong O-H···O hydrogen bonds (Table 1), forming directed 4-membered cooperative O—H···O—H···O—H···O—H rings (Fig. 2). There are large void channels in the
(Fig. 3) containing residual electron density with high disorder.For the procedure adopted to reduce 1,3,5-tris(p-tolyl)pentane-1,5-dione, see: Paul et al. (2012). For a less green reported synthesis of the starting diketone, 1,3,5-tris(p-tolyl)pentane-1,5-dione, see: Yang et al. (2005). For applications of related compounds, see: Sundberg & Faergemann (2008). For the crystal structures of related compounds, see: Ha & Young (2009); Barrett et al. (2000). For details of the use of the SQUEEZE and CAVITY routines in PLATON, see: Spek (2009). For bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).C26H30O2 | Dx = 0.994 Mg m−3 |
Mr = 374.50 | Melting point: 373(2) K |
Trigonal, P3121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 31 2" | Cell parameters from 10976 reflections |
a = 14.6205 (5) Å | θ = 3.2–30.9° |
c = 20.2672 (6) Å | µ = 0.06 mm−1 |
V = 3751.9 (3) Å3 | T = 123 K |
Z = 6 | Plate, colourless |
F(000) = 1212 | 0.98 × 0.66 × 0.17 mm |
Agilent Xcalibur Ruby Gemini diffractometer | 7200 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5765 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 30.9°, θmin = 3.2° |
ω scans | h = −20→18 |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), using a multifaceted crystal model (Clark & Reid, 1995)] | k = −13→19 |
Tmin = 0.957, Tmax = 0.990 | l = −28→26 |
35176 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.193 | w = 1/[σ2(Fo2) + (0.1162P)2 + 0.2294P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
7200 reflections | Δρmax = 0.32 e Å−3 |
258 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack parameter determined using 2073 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.3 (4) |
C26H30O2 | Z = 6 |
Mr = 374.50 | Mo Kα radiation |
Trigonal, P3121 | µ = 0.06 mm−1 |
a = 14.6205 (5) Å | T = 123 K |
c = 20.2672 (6) Å | 0.98 × 0.66 × 0.17 mm |
V = 3751.9 (3) Å3 |
Agilent Xcalibur Ruby Gemini diffractometer | 7200 independent reflections |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), using a multifaceted crystal model (Clark & Reid, 1995)] | 5765 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.990 | Rint = 0.034 |
35176 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.193 | Δρmax = 0.32 e Å−3 |
S = 1.08 | Δρmin = −0.24 e Å−3 |
7200 reflections | Absolute structure: Flack parameter determined using 2073 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
258 parameters | Absolute structure parameter: −0.3 (4) |
0 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.55511 (15) | 0.01657 (13) | 0.24921 (8) | 0.0403 (5) | |
O5 | 0.53998 (13) | 0.37108 (12) | 0.01023 (8) | 0.0342 (4) | |
C1 | 0.5100 (2) | 0.00501 (17) | 0.18436 (10) | 0.0318 (6) | |
C2 | 0.54021 (19) | 0.11650 (16) | 0.16162 (10) | 0.0317 (6) | |
C3 | 0.49968 (18) | 0.12147 (16) | 0.09253 (11) | 0.0300 (5) | |
C4 | 0.53487 (19) | 0.23812 (17) | 0.07835 (11) | 0.0319 (6) | |
C5 | 0.49703 (18) | 0.25811 (17) | 0.01230 (10) | 0.0302 (5) | |
C11 | 0.5478 (2) | −0.04987 (17) | 0.13833 (11) | 0.0339 (6) | |
C12 | 0.6544 (2) | −0.0129 (2) | 0.12939 (15) | 0.0483 (8) | |
C13 | 0.6873 (3) | −0.0652 (3) | 0.08777 (17) | 0.0600 (10) | |
C14 | 0.6155 (3) | −0.1550 (2) | 0.05386 (15) | 0.0557 (8) | |
C15 | 0.5101 (3) | −0.1911 (2) | 0.06246 (14) | 0.0498 (8) | |
C16 | 0.4758 (2) | −0.13936 (19) | 0.10424 (12) | 0.0404 (7) | |
C17 | 0.6518 (4) | −0.2152 (3) | 0.0109 (2) | 0.0859 (15) | |
C31 | 0.38070 (19) | 0.04976 (17) | 0.08632 (11) | 0.0322 (6) | |
C32 | 0.3383 (2) | −0.02456 (19) | 0.03540 (12) | 0.0397 (7) | |
C33 | 0.2302 (3) | −0.0923 (2) | 0.03095 (16) | 0.0539 (9) | |
C34 | 0.1600 (2) | −0.0889 (3) | 0.07530 (16) | 0.0571 (9) | |
C35 | 0.2037 (3) | −0.0131 (3) | 0.12548 (17) | 0.0622 (10) | |
C36 | 0.3115 (2) | 0.0543 (2) | 0.13062 (14) | 0.0481 (8) | |
C37 | 0.0412 (3) | −0.1620 (4) | 0.0702 (2) | 0.0889 (16) | |
C51 | 0.53006 (17) | 0.22032 (16) | −0.04816 (10) | 0.0292 (5) | |
C52 | 0.6275 (2) | 0.2274 (2) | −0.05428 (13) | 0.0433 (7) | |
C53 | 0.6561 (2) | 0.1949 (2) | −0.11143 (15) | 0.0492 (8) | |
C54 | 0.5862 (3) | 0.1539 (2) | −0.16445 (13) | 0.0468 (8) | |
C55 | 0.4884 (3) | 0.1454 (2) | −0.15807 (12) | 0.0451 (8) | |
C56 | 0.46012 (19) | 0.17721 (18) | −0.10069 (12) | 0.0354 (6) | |
C57 | 0.6178 (3) | 0.1197 (3) | −0.22690 (16) | 0.0670 (11) | |
H1 | 0.43133 | −0.03813 | 0.18794 | 0.0382* | |
H1A | 0.52364 | −0.04149 | 0.26918 | 0.0605* | |
H2A | 0.61815 | 0.16084 | 0.16195 | 0.0380* | |
H2B | 0.51202 | 0.14717 | 0.19375 | 0.0380* | |
H3 | 0.53468 | 0.09783 | 0.05974 | 0.0360* | |
H4A | 0.50846 | 0.26475 | 0.11424 | 0.0382* | |
H4B | 0.61299 | 0.27957 | 0.07938 | 0.0382* | |
H5 | 0.41821 | 0.22284 | 0.01313 | 0.0363* | |
H5A | 0.51238 | 0.38632 | −0.02110 | 0.0513* | |
H12 | 0.70497 | 0.04879 | 0.15198 | 0.0580* | |
H13 | 0.76073 | −0.03920 | 0.08220 | 0.0720* | |
H15 | 0.45977 | −0.25238 | 0.03949 | 0.0598* | |
H16 | 0.40227 | −0.16546 | 0.10955 | 0.0485* | |
H17A | 0.59274 | −0.26614 | −0.01624 | 0.1289* | |
H17B | 0.67692 | −0.25282 | 0.03889 | 0.1289* | |
H17C | 0.70936 | −0.16569 | −0.01775 | 0.1289* | |
H32 | 0.38386 | −0.02867 | 0.00364 | 0.0476* | |
H33 | 0.20335 | −0.14266 | −0.00376 | 0.0647* | |
H35 | 0.15810 | −0.00787 | 0.15675 | 0.0745* | |
H36 | 0.33833 | 0.10473 | 0.16531 | 0.0577* | |
H37A | 0.01162 | −0.13200 | 0.03937 | 0.1333* | |
H37B | 0.00906 | −0.16974 | 0.11381 | 0.1333* | |
H37C | 0.02635 | −0.23137 | 0.05424 | 0.1333* | |
H52 | 0.67616 | 0.25504 | −0.01868 | 0.0519* | |
H53 | 0.72368 | 0.20062 | −0.11431 | 0.0590* | |
H55 | 0.43948 | 0.11734 | −0.19350 | 0.0542* | |
H56 | 0.39173 | 0.16933 | −0.09732 | 0.0425* | |
H57A | 0.69271 | 0.14053 | −0.22448 | 0.1001* | |
H57B | 0.60609 | 0.15363 | −0.26511 | 0.1001* | |
H57C | 0.57511 | 0.04281 | −0.23148 | 0.1001* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0659 (10) | 0.0270 (7) | 0.0187 (7) | 0.0162 (7) | −0.0097 (7) | 0.0014 (6) |
O5 | 0.0541 (8) | 0.0381 (7) | 0.0228 (7) | 0.0324 (5) | 0.0016 (6) | 0.0036 (6) |
C1 | 0.0456 (11) | 0.0261 (9) | 0.0183 (9) | 0.0138 (8) | −0.0049 (8) | 0.0008 (8) |
C2 | 0.0488 (11) | 0.0275 (9) | 0.0201 (9) | 0.0200 (7) | −0.0071 (8) | −0.0015 (8) |
C3 | 0.0446 (10) | 0.0301 (9) | 0.0172 (9) | 0.0201 (7) | −0.0031 (8) | −0.0016 (7) |
C4 | 0.0493 (11) | 0.0324 (9) | 0.0173 (9) | 0.0229 (8) | −0.0018 (8) | 0.0010 (8) |
C5 | 0.0408 (10) | 0.0349 (9) | 0.0200 (9) | 0.0227 (7) | 0.0022 (8) | 0.0040 (8) |
C11 | 0.0524 (12) | 0.0316 (9) | 0.0208 (10) | 0.0233 (8) | −0.0057 (9) | 0.0030 (8) |
C12 | 0.0599 (14) | 0.0438 (12) | 0.0459 (15) | 0.0294 (10) | −0.0116 (12) | 0.0005 (11) |
C13 | 0.0758 (17) | 0.0673 (15) | 0.0563 (19) | 0.0503 (12) | 0.0013 (15) | 0.0070 (14) |
C14 | 0.1000 (17) | 0.0589 (12) | 0.0368 (14) | 0.0612 (10) | 0.0034 (13) | 0.0063 (11) |
C15 | 0.0887 (17) | 0.0421 (11) | 0.0316 (12) | 0.0424 (10) | −0.0113 (12) | −0.0054 (10) |
C16 | 0.0628 (13) | 0.0343 (10) | 0.0281 (11) | 0.0272 (9) | −0.0091 (10) | −0.0010 (9) |
C17 | 0.135 (3) | 0.0825 (18) | 0.079 (3) | 0.0834 (15) | 0.012 (2) | −0.0041 (19) |
C31 | 0.0447 (10) | 0.0322 (9) | 0.0206 (10) | 0.0198 (8) | −0.0021 (8) | 0.0023 (8) |
C32 | 0.0535 (13) | 0.0381 (10) | 0.0250 (11) | 0.0210 (9) | −0.0023 (10) | −0.0008 (9) |
C33 | 0.0650 (17) | 0.0467 (14) | 0.0375 (15) | 0.0186 (12) | −0.0141 (13) | −0.0031 (11) |
C34 | 0.0486 (15) | 0.0633 (18) | 0.0431 (15) | 0.0157 (13) | −0.0014 (12) | 0.0070 (14) |
C35 | 0.0505 (15) | 0.081 (2) | 0.0465 (17) | 0.0265 (14) | 0.0079 (13) | 0.0019 (16) |
C36 | 0.0528 (14) | 0.0574 (14) | 0.0322 (13) | 0.0262 (11) | −0.0015 (11) | −0.0078 (12) |
C37 | 0.057 (2) | 0.095 (3) | 0.076 (3) | 0.009 (2) | −0.0101 (19) | 0.001 (2) |
C51 | 0.0420 (10) | 0.0292 (8) | 0.0196 (9) | 0.0201 (7) | 0.0035 (8) | 0.0036 (7) |
C52 | 0.0462 (12) | 0.0551 (13) | 0.0317 (12) | 0.0277 (10) | −0.0022 (10) | −0.0068 (11) |
C53 | 0.0489 (12) | 0.0564 (14) | 0.0455 (15) | 0.0287 (10) | 0.0068 (11) | −0.0089 (12) |
C54 | 0.0685 (15) | 0.0443 (12) | 0.0270 (12) | 0.0278 (11) | 0.0097 (11) | −0.0023 (10) |
C55 | 0.0658 (16) | 0.0429 (12) | 0.0218 (11) | 0.0235 (11) | −0.0053 (11) | −0.0040 (9) |
C56 | 0.0425 (11) | 0.0367 (10) | 0.0281 (11) | 0.0206 (8) | −0.0003 (9) | 0.0012 (9) |
C57 | 0.090 (2) | 0.0742 (19) | 0.0391 (16) | 0.0428 (15) | 0.0168 (15) | −0.0107 (14) |
O1—C1 | 1.442 (3) | C54—C57 | 1.515 (5) |
O5—C5 | 1.445 (3) | C55—C56 | 1.390 (4) |
O1—H1A | 0.8400 | C1—H1 | 1.0000 |
O5—H5A | 0.8400 | C2—H2A | 0.9900 |
C1—C11 | 1.504 (4) | C2—H2B | 0.9900 |
C1—C2 | 1.531 (3) | C3—H3 | 1.0000 |
C2—C3 | 1.536 (3) | C4—H4A | 0.9900 |
C3—C4 | 1.542 (3) | C4—H4B | 0.9900 |
C3—C31 | 1.522 (4) | C5—H5 | 1.0000 |
C4—C5 | 1.531 (3) | C12—H12 | 0.9500 |
C5—C51 | 1.519 (3) | C13—H13 | 0.9500 |
C11—C16 | 1.386 (3) | C15—H15 | 0.9500 |
C11—C12 | 1.383 (4) | C16—H16 | 0.9500 |
C12—C13 | 1.377 (5) | C17—H17A | 0.9800 |
C13—C14 | 1.386 (5) | C17—H17B | 0.9800 |
C14—C17 | 1.511 (6) | C17—H17C | 0.9800 |
C14—C15 | 1.368 (6) | C32—H32 | 0.9500 |
C15—C16 | 1.386 (5) | C33—H33 | 0.9500 |
C31—C32 | 1.399 (3) | C35—H35 | 0.9500 |
C31—C36 | 1.379 (4) | C36—H36 | 0.9500 |
C32—C33 | 1.386 (5) | C37—H37A | 0.9800 |
C33—C34 | 1.384 (5) | C37—H37B | 0.9800 |
C34—C35 | 1.401 (5) | C37—H37C | 0.9800 |
C34—C37 | 1.521 (6) | C52—H52 | 0.9500 |
C35—C36 | 1.383 (5) | C53—H53 | 0.9500 |
C51—C56 | 1.390 (3) | C55—H55 | 0.9500 |
C51—C52 | 1.381 (4) | C56—H56 | 0.9500 |
C52—C53 | 1.393 (4) | C57—H57A | 0.9800 |
C53—C54 | 1.395 (4) | C57—H57B | 0.9800 |
C54—C55 | 1.378 (7) | C57—H57C | 0.9800 |
C1—O1—H1A | 109.00 | C4—C3—H3 | 108.00 |
C5—O5—H5A | 109.00 | C31—C3—H3 | 108.00 |
C2—C1—C11 | 113.19 (19) | C3—C4—H4A | 109.00 |
O1—C1—C2 | 106.14 (17) | C3—C4—H4B | 109.00 |
O1—C1—C11 | 111.1 (2) | C5—C4—H4A | 109.00 |
C1—C2—C3 | 114.33 (17) | C5—C4—H4B | 109.00 |
C2—C3—C31 | 112.19 (19) | H4A—C4—H4B | 108.00 |
C4—C3—C31 | 112.4 (2) | O5—C5—H5 | 109.00 |
C2—C3—C4 | 107.39 (17) | C4—C5—H5 | 109.00 |
C3—C4—C5 | 114.92 (18) | C51—C5—H5 | 109.00 |
O5—C5—C51 | 110.92 (17) | C11—C12—H12 | 120.00 |
O5—C5—C4 | 104.57 (17) | C13—C12—H12 | 120.00 |
C4—C5—C51 | 115.1 (2) | C12—C13—H13 | 119.00 |
C12—C11—C16 | 118.7 (3) | C14—C13—H13 | 119.00 |
C1—C11—C12 | 121.0 (2) | C14—C15—H15 | 120.00 |
C1—C11—C16 | 120.3 (3) | C16—C15—H15 | 120.00 |
C11—C12—C13 | 120.1 (3) | C11—C16—H16 | 120.00 |
C12—C13—C14 | 121.4 (4) | C15—C16—H16 | 120.00 |
C15—C14—C17 | 120.3 (3) | C14—C17—H17A | 109.00 |
C13—C14—C15 | 118.4 (3) | C14—C17—H17B | 109.00 |
C13—C14—C17 | 121.2 (4) | C14—C17—H17C | 109.00 |
C14—C15—C16 | 120.9 (3) | H17A—C17—H17B | 109.00 |
C11—C16—C15 | 120.6 (3) | H17A—C17—H17C | 110.00 |
C3—C31—C36 | 121.8 (2) | H17B—C17—H17C | 109.00 |
C3—C31—C32 | 120.4 (2) | C31—C32—H32 | 120.00 |
C32—C31—C36 | 117.8 (3) | C33—C32—H32 | 120.00 |
C31—C32—C33 | 120.5 (3) | C32—C33—H33 | 119.00 |
C32—C33—C34 | 122.2 (3) | C34—C33—H33 | 119.00 |
C35—C34—C37 | 120.9 (3) | C34—C35—H35 | 119.00 |
C33—C34—C37 | 122.5 (3) | C36—C35—H35 | 119.00 |
C33—C34—C35 | 116.5 (3) | C31—C36—H36 | 119.00 |
C34—C35—C36 | 121.7 (4) | C35—C36—H36 | 119.00 |
C31—C36—C35 | 121.3 (3) | C34—C37—H37A | 109.00 |
C52—C51—C56 | 117.6 (2) | C34—C37—H37B | 109.00 |
C5—C51—C52 | 123.3 (2) | C34—C37—H37C | 110.00 |
C5—C51—C56 | 119.2 (2) | H37A—C37—H37B | 109.00 |
C51—C52—C53 | 121.6 (3) | H37A—C37—H37C | 110.00 |
C52—C53—C54 | 120.4 (3) | H37B—C37—H37C | 109.00 |
C53—C54—C57 | 120.4 (4) | C51—C52—H52 | 119.00 |
C53—C54—C55 | 118.1 (3) | C53—C52—H52 | 119.00 |
C55—C54—C57 | 121.5 (3) | C52—C53—H53 | 120.00 |
C54—C55—C56 | 121.1 (3) | C54—C53—H53 | 120.00 |
C51—C56—C55 | 121.2 (3) | C54—C55—H55 | 119.00 |
O1—C1—H1 | 109.00 | C56—C55—H55 | 119.00 |
C2—C1—H1 | 109.00 | C51—C56—H56 | 119.00 |
C11—C1—H1 | 109.00 | C55—C56—H56 | 119.00 |
C1—C2—H2A | 109.00 | C54—C57—H57A | 109.00 |
C1—C2—H2B | 109.00 | C54—C57—H57B | 109.00 |
C3—C2—H2A | 109.00 | C54—C57—H57C | 109.00 |
C3—C2—H2B | 109.00 | H57A—C57—H57B | 109.00 |
H2A—C2—H2B | 108.00 | H57A—C57—H57C | 109.00 |
C2—C3—H3 | 108.00 | H57B—C57—H57C | 109.00 |
O1—C1—C2—C3 | 179.7 (2) | C12—C13—C14—C15 | 0.1 (5) |
C11—C1—C2—C3 | 57.6 (3) | C12—C13—C14—C17 | −176.9 (3) |
O1—C1—C11—C12 | −53.8 (3) | C13—C14—C15—C16 | −0.2 (5) |
O1—C1—C11—C16 | 125.8 (2) | C17—C14—C15—C16 | 176.9 (3) |
C2—C1—C11—C12 | 65.4 (3) | C14—C15—C16—C11 | −0.1 (4) |
C2—C1—C11—C16 | −115.0 (3) | C3—C31—C32—C33 | 177.9 (2) |
C1—C2—C3—C4 | 178.8 (2) | C36—C31—C32—C33 | −1.2 (4) |
C1—C2—C3—C31 | 54.8 (3) | C3—C31—C36—C35 | −178.3 (3) |
C2—C3—C4—C5 | −177.4 (2) | C32—C31—C36—C35 | 0.7 (4) |
C31—C3—C4—C5 | −53.5 (3) | C31—C32—C33—C34 | 0.9 (5) |
C2—C3—C31—C32 | −126.6 (2) | C32—C33—C34—C35 | −0.1 (5) |
C2—C3—C31—C36 | 52.4 (3) | C32—C33—C34—C37 | 179.2 (3) |
C4—C3—C31—C32 | 112.3 (3) | C33—C34—C35—C36 | −0.4 (5) |
C4—C3—C31—C36 | −68.7 (3) | C37—C34—C35—C36 | −179.7 (4) |
C3—C4—C5—O5 | −179.6 (2) | C34—C35—C36—C31 | 0.1 (5) |
C3—C4—C5—C51 | −57.6 (3) | C5—C51—C52—C53 | −177.9 (2) |
O5—C5—C51—C52 | 80.7 (3) | C56—C51—C52—C53 | 1.4 (4) |
O5—C5—C51—C56 | −98.7 (2) | C5—C51—C56—C55 | 177.4 (2) |
C4—C5—C51—C52 | −37.8 (3) | C52—C51—C56—C55 | −1.9 (3) |
C4—C5—C51—C56 | 142.9 (2) | C51—C52—C53—C54 | 0.0 (4) |
C1—C11—C12—C13 | 179.0 (3) | C52—C53—C54—C55 | −0.9 (4) |
C16—C11—C12—C13 | −0.6 (4) | C52—C53—C54—C57 | 179.3 (3) |
C1—C11—C16—C15 | −179.1 (2) | C53—C54—C55—C56 | 0.4 (4) |
C12—C11—C16—C15 | 0.5 (4) | C57—C54—C55—C56 | −179.8 (3) |
C11—C12—C13—C14 | 0.3 (5) | C54—C55—C56—C51 | 1.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O5i | 0.84 | 1.95 | 2.786 (3) | 174 |
O5—H5A···O1ii | 0.84 | 1.89 | 2.716 (3) | 170 |
Symmetry codes: (i) −x+1, −x+y, −z+1/3; (ii) −x+y+1, −x+1, z−1/3. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O5i | 0.84 | 1.95 | 2.786 (3) | 174 |
O5—H5A···O1ii | 0.84 | 1.89 | 2.716 (3) | 170 |
Symmetry codes: (i) −x+1, −x+y, −z+1/3; (ii) −x+y+1, −x+1, z−1/3. |
Acknowledgements
RJB acknowledges the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer.
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The synthesis of the title compound has been achieved by the sodium borohydride reduction of the corresponding 1,5-diketone by a method reported recently (Paul et al. 2012). The starting diketone, 1,3,5-tris-(p-tolyl)pentane-1,5-dione, was prepared by a greener route slightly deviating from the reported one (Yang et al. 2005). Though, the separation of the diastereomeric mixture posed problems, it was possible to get one diastereomer in pure form. This acyclic pentane-1,5-diol can be employed for the generation of heterocyclic compounds like tetrahydropyran. Generally, pentane-1,5-diol derivatives are found to be more valuable than several other diols in connection with drug delivery-enhancing potency, pharmaceutical and cosmetic properties, antimicrobial spectrum and toxicity (Sundberg & Faergemann, 2008). The related compounds whose structures have been solved by X-ray diffraction analysis are 2,2,3,3,4,4-hexafluoropentane-1,5-diol (Ha et al. 2009) and 3-methylenepentane-1,5-diols (Barrett et al. 2000).
In the title molecule, Fig. 1, the pentane-1,5-diol unit (C1—C5/O1/O5) forms a regular zigzag pattern with torsion angles C1—C2—C3—C4 = 178.8 (2)° and C2—C3—C4—C5 = -177.4 (2)°, with the two diol groups pointing in opposite directions. The central benzene ring (C31-C36) forms dihedral angles of 14.85 (15) and 28.17 (14)° with the two terminal benzene rings (C11-C16 and C51-C56, respectively). The dihedral angle between the two terminal benzene rings is 32.14 (13)°. The C—C, Car—Car and C—O bond lengths are within their normal ranges (Allen et al., 1987).
In the crystal, there are two strong O-H···O hydrogen bonds (Table 1), forming directed 4-membered cooperative O—H···O—H···O—H···O—H rings (Fig. 2). There are large void channels in the crystal structure (Fig. 3) containing residual electron density with high disorder.