2-Methyl-4-phenyl­buta-2,3-dien-1-ol

The crystal structure of the title compound, C₁₁H₁₂O, a substrate for gold-catalysed cyclo­isomerization reactions [Hoffmann-Röder & Krause (2001). Org. Lett. 3, 2537–2538], contains two mol­ecules in the asymmetric unit. There are two inter­molecular O—H ... O hydrogen bonds in the crystal structure and a chain of mol­ecules is formed along the c axis via these hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.039
• wR factor = 0.084
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         32 Perc.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         11

Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C11 H12 O

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.45
           From the CIF: _reflns_number_total               1832
           Count of symmetry unique reflns         1867
           Completeness (_total/calc)             98.13%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).

2-Methyl-4-phenylbuta-2,3-dien-1-ol

Crystal data

C11H12O	F(000) = 688
Mr = 160.21	Dx = 1.138 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 17261 reflections
a = 24.379 (6) Å	θ = 3.1–25.1°
b = 9.601 (2) Å	µ = 0.07 mm^−1
c = 7.991 (3) Å	T = 173 K
V = 1870.4 (9) Å^3	Needle, colourless
Z = 8	0.15 × 0.08 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 25.5°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −29→29
341 frames via ω–rotation (Δω=1°) and two times 80 s per frame (four sets at different κ–angles) scans	k = −11→11
17261 measured reflections	l = −9→9
1832 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 1.00	w = [exp(4.2(sinθ/λ)^2)]/[σ^2(Fo^2)]
1832 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.11 e Å^−3
1 restraint	Δρmin = −0.11 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.01022 (16)	−0.6427 (4)	−0.0840 (6)	0.0752 (12)
H1	0.0239	−0.6100	0.0041	0.113*
O1'	0.04989 (14)	−0.4811 (3)	0.1676 (6)	0.0680 (11)
H1'	0.0278	−0.4302	0.2204	0.102*
C1	0.1463 (3)	−0.4429 (7)	−0.3628 (10)	0.0604 (19)
C2	0.1491 (3)	−0.3067 (8)	−0.4280 (9)	0.073 (3)
H2	0.1221	−0.2768	−0.5058	0.088*
C3	0.1901 (3)	−0.2160 (7)	−0.3816 (12)	0.080 (3)
H3	0.1916	−0.1257	−0.4298	0.096*
C4	0.2292 (3)	−0.2557 (9)	−0.2649 (11)	0.082 (3)
H4	0.2570	−0.1921	−0.2318	0.098*
C5	0.2277 (3)	−0.3879 (9)	−0.1968 (9)	0.075 (3)
H5	0.2545	−0.4160	−0.1172	0.090*
C6	0.1859 (3)	−0.4808 (8)	−0.2469 (9)	0.070 (2)
H6	0.1850	−0.5716	−0.2000	0.084*
C7	0.1015 (3)	−0.5389 (7)	−0.4103 (10)	0.069 (2)
H7	0.0794	−0.5126	−0.5030	0.083*
C8	0.0895 (3)	−0.6551 (7)	−0.3376 (11)	0.063 (2)
C9	0.0756 (3)	−0.7686 (8)	−0.2635 (9)	0.063 (2)
C10	0.0343 (3)	−0.7743 (6)	−0.1191 (10)	0.075 (2)
H10A	0.0050	−0.8415	−0.1474	0.090*
H10B	0.0531	−0.8087	−0.0173	0.090*
C11	0.0960 (3)	−0.9133 (6)	−0.3159 (11)	0.088 (3)
H11A	0.0656	−0.9666	−0.3638	0.132*
H11B	0.1105	−0.9624	−0.2178	0.132*
H11C	0.1252	−0.9034	−0.3996	0.132*
C1'	0.1446 (3)	0.0675 (7)	0.1558 (11)	0.063 (2)
C2'	0.1458 (3)	0.1997 (8)	0.2218 (9)	0.073 (3)
H2'	0.1179	0.2293	0.2970	0.087*
C3'	0.1883 (3)	0.2906 (8)	0.1776 (12)	0.084 (3)
H3'	0.1892	0.3827	0.2209	0.101*
C4'	0.2288 (3)	0.2451 (10)	0.0708 (11)	0.080 (3)
H4'	0.2581	0.3057	0.0412	0.096*
C5'	0.2271 (3)	0.1123 (10)	0.0070 (9)	0.076 (3)
H5'	0.2554	0.0824	−0.0663	0.091*
C6'	0.1856 (3)	0.0220 (7)	0.0466 (9)	0.065 (2)
H6'	0.1847	−0.0693	0.0009	0.078*
C7'	0.0984 (3)	−0.0256 (7)	0.1990 (10)	0.073 (2)
H7'	0.0766	−0.0007	0.2929	0.088*
C8'	0.0845 (3)	−0.1437 (8)	0.1159 (11)	0.072 (2)
C9'	0.0702 (3)	−0.2593 (8)	0.0383 (10)	0.073 (3)
C10'	0.0922 (3)	−0.3971 (6)	0.0973 (10)	0.071 (2)
H10C	0.1091	−0.4468	0.0018	0.085*
H10D	0.1211	−0.3810	0.1824	0.085*
C11'	0.0305 (3)	−0.2568 (7)	−0.1073 (9)	0.081 (2)
H11D	0.0151	−0.1630	−0.1190	0.121*
H11E	0.0008	−0.3235	−0.0868	0.121*
H11F	0.0499	−0.2823	−0.2103	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.073 (3)	0.081 (3)	0.071 (3)	0.003 (2)	0.002 (2)	−0.008 (3)
O1'	0.063 (2)	0.068 (3)	0.073 (3)	0.001 (2)	0.013 (2)	−0.001 (2)
C1	0.055 (4)	0.065 (5)	0.062 (6)	0.006 (4)	0.009 (5)	0.004 (5)
C2	0.062 (5)	0.079 (6)	0.078 (7)	0.013 (4)	0.008 (4)	0.011 (5)
C3	0.080 (6)	0.059 (5)	0.100 (8)	−0.008 (5)	0.021 (6)	−0.003 (5)
C4	0.066 (6)	0.077 (8)	0.102 (9)	−0.013 (5)	0.003 (5)	−0.011 (5)
C5	0.067 (6)	0.079 (8)	0.078 (7)	0.005 (5)	−0.002 (4)	−0.012 (5)
C6	0.054 (5)	0.085 (6)	0.072 (6)	0.007 (5)	0.003 (4)	0.011 (5)
C7	0.049 (4)	0.072 (5)	0.086 (7)	0.007 (4)	−0.009 (4)	0.001 (5)
C8	0.062 (4)	0.059 (5)	0.067 (6)	−0.003 (4)	−0.008 (4)	0.003 (5)
C9	0.058 (5)	0.077 (6)	0.055 (6)	−0.003 (4)	−0.014 (4)	−0.001 (4)
C10	0.067 (5)	0.066 (5)	0.091 (7)	−0.006 (4)	−0.014 (5)	−0.008 (5)
C11	0.092 (5)	0.067 (5)	0.105 (7)	0.010 (4)	−0.026 (6)	−0.002 (5)
C1'	0.059 (5)	0.057 (5)	0.075 (6)	−0.010 (4)	−0.012 (5)	0.009 (5)
C2'	0.071 (5)	0.055 (5)	0.092 (8)	0.000 (4)	−0.014 (4)	0.000 (5)
C3'	0.095 (7)	0.063 (6)	0.094 (8)	0.009 (5)	−0.037 (6)	−0.018 (6)
C4'	0.079 (6)	0.076 (7)	0.084 (8)	−0.013 (5)	−0.018 (5)	0.010 (5)
C5'	0.067 (6)	0.075 (7)	0.085 (7)	−0.003 (5)	−0.007 (4)	−0.003 (5)
C6'	0.074 (6)	0.052 (5)	0.069 (6)	0.002 (5)	−0.012 (4)	0.013 (4)
C7'	0.071 (5)	0.074 (5)	0.076 (7)	0.008 (5)	0.001 (4)	0.001 (5)
C8'	0.059 (5)	0.083 (5)	0.074 (6)	0.014 (5)	0.004 (5)	0.005 (5)
C9'	0.060 (5)	0.069 (6)	0.088 (8)	−0.012 (4)	0.017 (4)	−0.004 (5)
C10'	0.065 (5)	0.067 (5)	0.081 (6)	0.005 (4)	−0.006 (5)	−0.005 (4)
C11'	0.062 (5)	0.107 (6)	0.072 (7)	−0.011 (4)	0.002 (5)	−0.011 (6)

Geometric parameters (Å, º)

O1—C10	1.421 (6)	C11—H11B	0.9800
O1—H1	0.8400	C11—H11C	0.9800
O1'—C10'	1.425 (7)	C1'—C2'	1.375 (9)
O1'—H1'	0.8400	C1'—C6'	1.397 (8)
C1—C6	1.387 (8)	C1'—C7'	1.478 (8)
C1—C2	1.410 (8)	C2'—C3'	1.400 (9)
C1—C7	1.479 (8)	C2'—H2'	0.9500
C2—C3	1.376 (8)	C3'—C4'	1.377 (10)
C2—H2	0.9500	C3'—H3'	0.9500
C3—C4	1.387 (10)	C4'—C5'	1.374 (11)
C3—H3	0.9500	C4'—H4'	0.9500
C4—C5	1.381 (10)	C5'—C6'	1.371 (8)
C4—H4	0.9500	C5'—H5'	0.9500
C5—C6	1.411 (9)	C6'—H6'	0.9500
C5—H5	0.9500	C7'—C8'	1.357 (9)
C6—H6	0.9500	C7'—H7'	0.9500
C7—C8	1.291 (9)	C8'—C9'	1.318 (10)
C7—H7	0.9500	C9'—C10'	1.504 (9)
C8—C9	1.285 (9)	C9'—C11'	1.513 (9)
C9—C10	1.533 (9)	C10'—H10C	0.9900
C9—C11	1.535 (8)	C10'—H10D	0.9900
C10—H10A	0.9900	C11'—H11D	0.9800
C10—H10B	0.9900	C11'—H11E	0.9800
C11—H11A	0.9800	C11'—H11F	0.9800
C10—O1—H1	109.5	H11B—C11—H11C	109.5
C10'—O1'—H1'	109.5	C2'—C1'—C6'	120.9 (6)
C6—C1—C2	117.1 (7)	C2'—C1'—C7'	119.0 (8)
C6—C1—C7	121.5 (7)	C6'—C1'—C7'	120.1 (7)
C2—C1—C7	121.3 (7)	C1'—C2'—C3'	119.6 (8)
C3—C2—C1	121.5 (8)	C1'—C2'—H2'	120.2
C3—C2—H2	119.2	C3'—C2'—H2'	120.2
C1—C2—H2	119.2	C4'—C3'—C2'	119.3 (8)
C2—C3—C4	120.4 (8)	C4'—C3'—H3'	120.3
C2—C3—H3	119.8	C2'—C3'—H3'	120.3
C4—C3—H3	119.8	C5'—C4'—C3'	120.2 (8)
C5—C4—C3	120.0 (8)	C5'—C4'—H4'	119.9
C5—C4—H4	120.0	C3'—C4'—H4'	119.9
C3—C4—H4	120.0	C6'—C5'—C4'	121.6 (8)
C4—C5—C6	119.2 (7)	C6'—C5'—H5'	119.2
C4—C5—H5	120.4	C4'—C5'—H5'	119.2
C6—C5—H5	120.4	C5'—C6'—C1'	118.4 (7)
C1—C6—C5	121.8 (7)	C5'—C6'—H6'	120.8
C1—C6—H6	119.1	C1'—C6'—H6'	120.8
C5—C6—H6	119.1	C8'—C7'—C1'	125.5 (8)
C8—C7—C1	126.2 (7)	C8'—C7'—H7'	117.2
C8—C7—H7	116.9	C1'—C7'—H7'	117.2
C1—C7—H7	116.9	C9'—C8'—C7'	178.6 (8)
C9—C8—C7	177.5 (8)	C8'—C9'—C10'	119.8 (8)
C8—C9—C10	123.4 (7)	C8'—C9'—C11'	121.2 (7)
C8—C9—C11	123.8 (8)	C10'—C9'—C11'	118.9 (7)
C10—C9—C11	112.7 (6)	O1'—C10'—C9'	111.2 (5)
O1—C10—C9	112.8 (6)	O1'—C10'—H10C	109.4
O1—C10—H10A	109.0	C9'—C10'—H10C	109.4
C9—C10—H10A	109.0	O1'—C10'—H10D	109.4
O1—C10—H10B	109.0	C9'—C10'—H10D	109.4
C9—C10—H10B	109.0	H10C—C10'—H10D	108.0
H10A—C10—H10B	107.8	C9'—C11'—H11D	109.5
C9—C11—H11A	109.5	C9'—C11'—H11E	109.5
C9—C11—H11B	109.5	H11D—C11'—H11E	109.5
H11A—C11—H11B	109.5	C9'—C11'—H11F	109.5
C9—C11—H11C	109.5	H11D—C11'—H11F	109.5
H11A—C11—H11C	109.5	H11E—C11'—H11F	109.5
C6—C1—C2—C3	1.4 (11)	C6'—C1'—C2'—C3'	0.8 (11)
C7—C1—C2—C3	178.6 (7)	C7'—C1'—C2'—C3'	−177.9 (6)
C1—C2—C3—C4	−1.7 (12)	C1'—C2'—C3'—C4'	−1.2 (12)
C2—C3—C4—C5	1.2 (11)	C2'—C3'—C4'—C5'	0.7 (12)
C3—C4—C5—C6	−0.3 (11)	C3'—C4'—C5'—C6'	0.1 (12)
C2—C1—C6—C5	−0.5 (10)	C4'—C5'—C6'—C1'	−0.5 (11)
C7—C1—C6—C5	−177.8 (7)	C2'—C1'—C6'—C5'	0.1 (11)
C4—C5—C6—C1	0.0 (11)	C7'—C1'—C6'—C5'	178.7 (6)
C6—C1—C7—C8	10.0 (12)	C2'—C1'—C7'—C8'	163.6 (7)
C2—C1—C7—C8	−167.1 (8)	C6'—C1'—C7'—C8'	−15.1 (12)
C8—C9—C10—O1	4.2 (10)	C8'—C9'—C10'—O1'	112.0 (7)
C11—C9—C10—O1	−172.7 (5)	C11'—C9'—C10'—O1'	−66.4 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1′	0.84	1.91	2.717 (6)	162
O1′—H1′···O1^i	0.84	1.95	2.739 (6)	157

Symmetry code: (i) −x, −y−1, z+1/2.