1,3,5-Tri-p-tolyl-pentane-1,5-diol.

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 inter-molecular O-H⋯O hydrogen bonds, forming directed four-membered co-operative rings. A region of disordered electron density, most probably disordered ethyl acetate solvent mol-ecules, occupying voids of ca 519 Å(3) 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 refinement. The structure was refined as an inversion twin [absolute structure parameter = -0.3 (4)].

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

C26H30O2

M = 374.50

Trigonal,

a = 14.6205 (5) Å

c = 20.2672 (6) Å

V = 3751.9 (3) Å3

Z = 6

Mo Kα radiation

μ = 0.06 mm−1

T = 123 K

0.98 × 0.66 × 0.17 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), using a multifaceted crystal model (Clark & Reid, 1995 ▶)] T min = 0.957, T max = 0.990

35176 measured reflections

7200 independent reflections

5765 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.193

S = 1.08

7200 reflections

258 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack parameter determined using 2073 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: −0.3 (4)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400018X/su2686sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400018X/su2686Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400018X/su2686Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400018X/su2686Isup4.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .