Crystal structure of (Z)-1-phenyl-3-styryl-undeca-2-en-4,10-diyn-1-ol.

The mol-ecule of the title compound, C25H24O, obtained by acid-catalysed 1,3-migration of an alcohol group, is T-shaped. The planes of the two phenyl rings are inclined to one another by 81.9 (2)°. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains along [001].

Related literature

For the 1,3-migration of an alcoholic group adjacent to a vinyl group in the presence of a Lewis acid, see: Piotti & Alper (1997 ▸); Poloukhtine & Popik (2005 ▸). For catalytic cyclization of alcohols containing a number of unsaturated groups, see: Teo et al. (2014 ▸).

Experimental

Crystal data

C25H24O

M = 340.44

Trigonal,

a = 17.867 (2) Å

c = 5.3290 (6) Å

V = 1473.3 (4) Å3

Z = 3

Mo Kα radiation

μ = 0.07 mm−1

T = 103 K

0.34 × 0.04 × 0.04 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.74, T max = 1.00

14182 measured reflections

4846 independent reflections

2945 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.129

S = 0.98

4846 reflections

235 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014, PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S205698901402742X/su5038sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901402742X/su5038Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901402742X/su5038Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901402742X/su5038fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

c . DOI: 10.1107/S205698901402742X/su5038fig2.tif

A partial view along the c axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

Click here for additional data file.

. DOI: 10.1107/S205698901402742X/su5038fig3.tif

Reaction scheme.

CCDC reference: 1009363

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

C25H24O	Dx = 1.151 Mg m−3
Mr = 340.44	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P32	Cell parameters from 1285 reflections
a = 17.867 (2) Å	θ = 2.3–20.5°
c = 5.3290 (6) Å	µ = 0.07 mm−1
V = 1473.3 (4) Å3	T = 103 K
Z = 3	Needle, colourless
F(000) = 546	0.34 × 0.04 × 0.04 mm

Bruker Kappa APEXII CCD diffractometer	4846 independent reflections
Radiation source: fine-focus sealed tube	2945 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
ω and φ scan	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −23→14
Tmin = 0.74, Tmax = 1.00	k = −22→23
14182 measured reflections	l = −7→7

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3
4846 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.30859 (17)	0.59437 (17)	0.3483 (5)	0.0251 (7)
H1A	0.3463	0.6311	0.2521	0.038*
C1	0.3069 (3)	0.5136 (2)	0.3226 (7)	0.0199 (9)
H1	0.3048	0.4898	0.4940	0.024*
C2	0.2281 (2)	0.4484 (3)	0.1774 (7)	0.0197 (9)
C3	0.1897 (3)	0.3614 (3)	0.2407 (8)	0.0281 (10)
H3	0.2105	0.3441	0.3801	0.034*
C4	0.1209 (3)	0.2999 (3)	0.1007 (9)	0.0341 (12)
H4	0.0948	0.2407	0.1461	0.041*
C5	0.0899 (3)	0.3235 (3)	−0.1032 (9)	0.0333 (11)
H5	0.0434	0.2809	−0.1998	0.040*
C6	0.1275 (3)	0.4099 (3)	−0.1651 (8)	0.0305 (11)
H6	0.1060	0.4269	−0.3038	0.037*
C7	0.1962 (3)	0.4721 (3)	−0.0270 (8)	0.0272 (10)
H7	0.2216	0.5313	−0.0722	0.033*
C8	0.3878 (2)	0.5282 (2)	0.1948 (7)	0.0196 (9)
H8	0.4050	0.5639	0.0497	0.024*
C9	0.4386 (2)	0.4964 (2)	0.2634 (7)	0.0160 (8)
C10	0.5143 (2)	0.5153 (2)	0.1121 (7)	0.0171 (8)
H10	0.5253	0.5510	−0.0311	0.021*
C11	0.5691 (2)	0.4869 (2)	0.1575 (7)	0.0171 (8)
H11	0.5608	0.4552	0.3082	0.021*
C12	0.6413 (2)	0.5000 (2)	−0.0039 (7)	0.0173 (9)
C13	0.6850 (2)	0.4550 (2)	0.0458 (7)	0.0184 (9)
H13	0.6692	0.4182	0.1882	0.022*
C14	0.7511 (3)	0.4630 (3)	−0.1091 (8)	0.0220 (9)
H14	0.7805	0.4324	−0.0718	0.026*
C15	0.7739 (3)	0.5160 (3)	−0.3182 (7)	0.0245 (10)
H15	0.8184	0.5209	−0.4264	0.029*
C16	0.7321 (2)	0.5620 (3)	−0.3704 (7)	0.0231 (9)
H16	0.7482	0.5985	−0.5134	0.028*
C17	0.6665 (3)	0.5545 (3)	−0.2137 (7)	0.0204 (9)
H17	0.6385	0.5867	−0.2492	0.024*
C18	0.4152 (2)	0.4385 (3)	0.4758 (8)	0.0184 (8)
C19	0.3892 (2)	0.3880 (2)	0.6457 (7)	0.0201 (9)
C20	0.3519 (3)	0.3267 (3)	0.8553 (8)	0.0275 (10)
H20A	0.3052	0.3336	0.9313	0.033*
H20B	0.3973	0.3426	0.9844	0.033*
C21	0.3157 (3)	0.2328 (3)	0.7913 (8)	0.0310 (11)
H21A	0.2888	0.1977	0.9434	0.037*
H21B	0.3637	0.2235	0.7405	0.037*
C22	0.2484 (3)	0.2009 (3)	0.5807 (8)	0.0317 (11)
H22A	0.2021	0.2137	0.6248	0.038*
H22B	0.2760	0.2322	0.4237	0.038*
C23	0.2091 (3)	0.1044 (3)	0.5383 (9)	0.0467 (14)
H23A	0.1740	0.0881	0.3830	0.056*
H23B	0.2562	0.0913	0.5127	0.056*
C24	0.1549 (3)	0.0521 (3)	0.7450 (9)	0.0326 (11)
C25	0.1097 (3)	0.0105 (3)	0.9069 (10)	0.0431 (13)
H25	0.0727	−0.0235	1.0394	0.052*

	U11	U22	U33	U12	U13	U23
O1	0.0252 (16)	0.0188 (15)	0.0341 (17)	0.0130 (13)	0.0087 (14)	0.0019 (13)
C1	0.024 (2)	0.021 (2)	0.021 (2)	0.0159 (19)	0.0076 (18)	0.0067 (18)
C2	0.019 (2)	0.021 (2)	0.024 (2)	0.0129 (18)	0.0084 (18)	0.0036 (18)
C3	0.022 (2)	0.025 (2)	0.036 (3)	0.010 (2)	0.002 (2)	0.008 (2)
C4	0.026 (2)	0.026 (3)	0.047 (3)	0.010 (2)	0.003 (2)	0.005 (2)
C5	0.024 (2)	0.034 (3)	0.038 (3)	0.011 (2)	−0.001 (2)	−0.006 (2)
C6	0.031 (3)	0.035 (3)	0.030 (3)	0.020 (2)	−0.005 (2)	−0.002 (2)
C7	0.028 (2)	0.027 (2)	0.029 (2)	0.016 (2)	0.003 (2)	0.005 (2)
C8	0.020 (2)	0.018 (2)	0.021 (2)	0.0093 (18)	0.0026 (17)	0.0022 (17)
C9	0.016 (2)	0.0124 (19)	0.019 (2)	0.0071 (17)	−0.0012 (17)	−0.0009 (16)
C10	0.018 (2)	0.0110 (19)	0.019 (2)	0.0051 (17)	0.0007 (17)	0.0011 (16)
C11	0.019 (2)	0.015 (2)	0.017 (2)	0.0078 (18)	0.0010 (17)	0.0004 (16)
C12	0.014 (2)	0.017 (2)	0.020 (2)	0.0066 (17)	−0.0008 (17)	−0.0034 (17)
C13	0.018 (2)	0.019 (2)	0.018 (2)	0.0087 (18)	0.0014 (17)	0.0001 (17)
C14	0.021 (2)	0.025 (2)	0.024 (2)	0.0145 (19)	−0.0020 (18)	−0.0037 (19)
C15	0.019 (2)	0.031 (2)	0.023 (2)	0.012 (2)	0.0035 (18)	−0.0035 (19)
C16	0.021 (2)	0.025 (2)	0.022 (2)	0.0096 (19)	0.0035 (18)	0.0020 (19)
C17	0.017 (2)	0.021 (2)	0.025 (2)	0.0119 (18)	−0.0006 (18)	0.0014 (18)
C18	0.015 (2)	0.020 (2)	0.021 (2)	0.0094 (17)	−0.0002 (17)	−0.0042 (18)
C19	0.017 (2)	0.020 (2)	0.021 (2)	0.0073 (18)	0.0002 (18)	0.0011 (18)
C20	0.031 (3)	0.024 (2)	0.020 (2)	0.008 (2)	−0.001 (2)	0.0045 (19)
C21	0.033 (3)	0.026 (2)	0.027 (2)	0.010 (2)	0.002 (2)	0.002 (2)
C22	0.032 (3)	0.024 (2)	0.029 (3)	0.006 (2)	0.003 (2)	0.003 (2)
C23	0.055 (3)	0.028 (3)	0.039 (3)	0.007 (2)	0.006 (3)	−0.002 (2)
C24	0.033 (3)	0.019 (2)	0.043 (3)	0.010 (2)	−0.004 (2)	−0.003 (2)
C25	0.037 (3)	0.029 (3)	0.054 (4)	0.009 (2)	0.001 (3)	0.006 (3)

O1—C1	1.435 (4)	C13—C14	1.388 (5)
O1—H1A	0.8400	C13—H13	0.9500
C1—C8	1.498 (5)	C14—C15	1.385 (6)
C1—C2	1.516 (6)	C14—H14	0.9500
C1—H1	1.0000	C15—C16	1.388 (6)
C2—C3	1.390 (5)	C15—H15	0.9500
C2—C7	1.390 (5)	C16—C17	1.390 (5)
C3—C4	1.387 (6)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.378 (6)	C18—C19	1.197 (5)
C4—H4	0.9500	C19—C20	1.470 (5)
C5—C6	1.381 (6)	C20—C21	1.504 (6)
C5—H5	0.9500	C20—H20A	0.9900
C6—C7	1.385 (6)	C20—H20B	0.9900
C6—H6	0.9500	C21—C22	1.531 (6)
C7—H7	0.9500	C21—H21A	0.9900
C8—C9	1.341 (5)	C21—H21B	0.9900
C8—H8	0.9500	C22—C23	1.519 (6)
C9—C18	1.446 (5)	C22—H22A	0.9900
C9—C10	1.461 (5)	C22—H22B	0.9900
C10—C11	1.332 (5)	C23—C24	1.456 (7)
C10—H10	0.9500	C23—H23A	0.9900
C11—C12	1.467 (5)	C23—H23B	0.9900
C11—H11	0.9500	C24—C25	1.161 (6)
C12—C13	1.399 (5)	C25—H25	0.9500
C12—C17	1.401 (5)
C1—O1—H1A	109.5	C12—C13—H13	119.4
O1—C1—C8	109.5 (3)	C15—C14—C13	119.5 (4)
O1—C1—C2	111.5 (3)	C15—C14—H14	120.2
C8—C1—C2	110.3 (3)	C13—C14—H14	120.2
O1—C1—H1	108.5	C14—C15—C16	120.3 (4)
C8—C1—H1	108.5	C14—C15—H15	119.9
C2—C1—H1	108.5	C16—C15—H15	119.9
C3—C2—C7	118.8 (4)	C15—C16—C17	120.1 (4)
C3—C2—C1	119.0 (4)	C15—C16—H16	120.0
C7—C2—C1	122.0 (4)	C17—C16—H16	120.0
C2—C3—C4	120.2 (4)	C16—C17—C12	120.6 (4)
C2—C3—H3	119.9	C16—C17—H17	119.7
C4—C3—H3	119.9	C12—C17—H17	119.7
C5—C4—C3	120.9 (4)	C19—C18—C9	174.8 (4)
C5—C4—H4	119.5	C18—C19—C20	176.0 (4)
C3—C4—H4	119.5	C19—C20—C21	116.2 (4)
C4—C5—C6	119.0 (4)	C19—C20—H20A	108.2
C4—C5—H5	120.5	C21—C20—H20A	108.2
C6—C5—H5	120.5	C19—C20—H20B	108.2
C5—C6—C7	120.7 (4)	C21—C20—H20B	108.2
C5—C6—H6	119.6	H20A—C20—H20B	107.4
C7—C6—H6	119.6	C20—C21—C22	113.6 (4)
C6—C7—C2	120.4 (4)	C20—C21—H21A	108.8
C6—C7—H7	119.8	C22—C21—H21A	108.8
C2—C7—H7	119.8	C20—C21—H21B	108.8
C9—C8—C1	126.9 (3)	C22—C21—H21B	108.8
C9—C8—H8	116.5	H21A—C21—H21B	107.7
C1—C8—H8	116.5	C23—C22—C21	111.3 (4)
C8—C9—C18	120.1 (3)	C23—C22—H22A	109.4
C8—C9—C10	119.7 (3)	C21—C22—H22A	109.4
C18—C9—C10	120.0 (3)	C23—C22—H22B	109.4
C11—C10—C9	125.7 (4)	C21—C22—H22B	109.4
C11—C10—H10	117.1	H22A—C22—H22B	108.0
C9—C10—H10	117.1	C24—C23—C22	113.4 (4)
C10—C11—C12	125.9 (4)	C24—C23—H23A	108.9
C10—C11—H11	117.0	C22—C23—H23A	108.9
C12—C11—H11	117.0	C24—C23—H23B	108.9
C13—C12—C17	118.2 (3)	C22—C23—H23B	108.9
C13—C12—C11	119.7 (4)	H23A—C23—H23B	107.7
C17—C12—C11	122.1 (3)	C25—C24—C23	178.0 (5)
C14—C13—C12	121.3 (4)	C24—C25—H25	180.0
C14—C13—H13	119.4
O1—C1—C2—C3	−145.9 (3)	C8—C9—C10—C11	−179.1 (4)
C8—C1—C2—C3	92.2 (4)	C18—C9—C10—C11	−3.5 (6)
O1—C1—C2—C7	38.1 (5)	C9—C10—C11—C12	175.0 (3)
C8—C1—C2—C7	−83.8 (4)	C10—C11—C12—C13	−169.7 (4)
C7—C2—C3—C4	0.2 (6)	C10—C11—C12—C17	8.1 (6)
C1—C2—C3—C4	−175.9 (4)	C17—C12—C13—C14	−0.6 (5)
C2—C3—C4—C5	0.4 (6)	C11—C12—C13—C14	177.2 (3)
C3—C4—C5—C6	−1.0 (7)	C12—C13—C14—C15	−0.6 (6)
C4—C5—C6—C7	1.0 (7)	C13—C14—C15—C16	1.1 (6)
C5—C6—C7—C2	−0.3 (7)	C14—C15—C16—C17	−0.5 (6)
C3—C2—C7—C6	−0.2 (6)	C15—C16—C17—C12	−0.8 (6)
C1—C2—C7—C6	175.8 (4)	C13—C12—C17—C16	1.3 (5)
O1—C1—C8—C9	133.8 (4)	C11—C12—C17—C16	−176.5 (4)
C2—C1—C8—C9	−103.1 (4)	C19—C20—C21—C22	−54.5 (5)
C1—C8—C9—C18	2.6 (6)	C20—C21—C22—C23	−175.6 (4)
C1—C8—C9—C10	178.2 (3)	C21—C22—C23—C24	68.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1i	0.84	1.83	2.652 (3)	166

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1AO1i	0.84	1.83	2.652(3)	166

Symmetry code: (i) .