Racemic trans-4-phen­ylperhydro­pyran-3-ol

In the title compound, C₁₁H₁₄O₂, the tetra­hydro­pyran ring adopts a ¹C₄ conformation, with the phen­yl and the hydr­oxy substituents located in equatorial positions. Hydrogen bonding occurs in the solid state between hydr­oxy groups to link two mol­ecules of (R,R)-trans-4-phen­ylperhydro­pyran-3-ol and two mol­ecules of the (S,S)-enantiomer to provide tetra­mers.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.062
• wR factor = 0.208
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.160
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.16

Alert level C
SHFSU01_ALERT_2_C  The absolute value of parameter shift to su ratio > 0.05
            Absolute value of the parameter shift to su ratio given   0.068
            Additional refinement cycles may be required.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT080_ALERT_2_C Maximum Shift/Error ............................       0.07
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT417_ALERT_2_C Short Inter D-H..H-D       H2C    ..  H4A     ..       2.10 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C11 H14 O2

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

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

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Computing details

Data collection: CAD-4 Diffractometer Control Software (Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990; Spek 2003) and ORTEP-3 for Windows (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.

trans-4-Phenyl-3-tetrahydropyranol

Crystal data

C11H14O2	F(000) = 384
Mr = 178.22	Dx = 1.236 Mg m^−3
Triclinic, P1	Melting point: 346 K
a = 9.580 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.015 (1) Å	Cell parameters from 25 reflections
c = 10.670 (2) Å	θ = 2.6–12.4°
α = 77.38 (1)°	µ = 0.08 mm^−1
β = 85.68 (2)°	T = 299 K
γ = 73.55 (1)°	Prism, colourless
V = 958.0 (4) Å^3	0.50 × 0.22 × 0.10 mm
Z = 4

Data collection

Nonius CAD-4 diffractometer	Rint = 0.160
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 4.2°
Graphite monochromator	h = −11→1
ω/2θ scans	k = −12→11
4247 measured reflections	l = −13→13
3738 independent reflections	3 standard reflections every 120 min
1776 reflections with I > 2σ(I)	intensity decay: 13.9%

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.113P)^2 + 0.3203P] where P = (Fo^2 + 2Fc^2)/3
3738 reflections	(Δ/σ)max = 0.068
241 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.32 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
C2	0.3676 (4)	0.3320 (3)	0.1975 (4)	0.0485 (8)
H2A	0.3009	0.3645	0.2645	0.058*
H2B	0.4491	0.3721	0.1944	0.058*
C3	0.4225 (3)	0.1719 (3)	0.2311 (3)	0.0375 (7)
H3	0.4954	0.1412	0.1662	0.045*
C4	0.2994 (3)	0.1027 (3)	0.2294 (3)	0.0381 (7)
H4	0.2307	0.1286	0.2986	0.046*
C5	0.2184 (4)	0.1668 (4)	0.1030 (3)	0.0477 (8)
H5A	0.2810	0.1365	0.0328	0.057*
H5B	0.1330	0.1325	0.1054	0.057*
C6	0.1726 (4)	0.3277 (4)	0.0797 (4)	0.0578 (10)
H6A	0.1230	0.3658	−0.0017	0.069*
H6B	0.1048	0.3580	0.1469	0.069*
C7	0.3541 (3)	−0.0594 (3)	0.2562 (3)	0.0386 (7)
C8	0.3338 (4)	−0.1367 (4)	0.3755 (3)	0.0500 (9)
H8	0.2845	−0.0903	0.4391	0.060*
C9	0.3864 (5)	−0.2841 (4)	0.4021 (4)	0.0659 (11)
H9	0.3724	−0.3356	0.4835	0.079*
C10	0.4590 (4)	−0.3542 (4)	0.3093 (4)	0.0645 (11)
H10	0.4934	−0.4529	0.3274	0.077*
C11	0.4802 (4)	−0.2783 (4)	0.1905 (4)	0.0601 (10)
H11	0.5297	−0.3252	0.1273	0.072*
C12	0.4281 (4)	−0.1316 (4)	0.1635 (3)	0.0495 (9)
H12	0.4430	−0.0807	0.0821	0.059*
C13	−0.1576 (4)	0.6642 (4)	0.3878 (4)	0.0633 (11)
H13A	−0.1032	0.6436	0.4661	0.076*
H13B	−0.2415	0.6269	0.4081	0.076*
C14	−0.2087 (3)	0.8237 (3)	0.3395 (3)	0.0442 (8)
H14	−0.2682	0.8440	0.2633	0.053*
C15	−0.0792 (3)	0.8846 (3)	0.3036 (3)	0.0400 (7)
H15	−0.0243	0.8658	0.3825	0.048*
C16	0.0210 (4)	0.8020 (4)	0.2112 (4)	0.0544 (9)
H16A	−0.0267	0.8233	0.1293	0.065*
H16B	0.1098	0.8317	0.1967	0.065*
C17	0.0577 (4)	0.6442 (4)	0.2649 (5)	0.0733 (13)
H17A	0.1167	0.5942	0.2026	0.088*
H17B	0.1146	0.6221	0.3419	0.088*
C18	−0.1230 (3)	1.0438 (3)	0.2552 (3)	0.0367 (7)
C19	−0.1881 (4)	1.1069 (4)	0.1370 (3)	0.0493 (8)
H19	−0.2044	1.0503	0.0843	0.059*
C20	−0.2289 (4)	1.2536 (4)	0.0968 (4)	0.0601 (10)
H20	−0.2721	1.2944	0.0172	0.072*
C21	−0.2066 (4)	1.3386 (4)	0.1725 (4)	0.0595 (10)
H21	−0.2350	1.4370	0.1450	0.071*
C22	−0.1426 (4)	1.2789 (4)	0.2886 (4)	0.0587 (10)
H22	−0.1273	1.3365	0.3407	0.070*
C23	−0.1001 (4)	1.1319 (3)	0.3292 (3)	0.0463 (8)
H23	−0.0551	1.0922	0.4082	0.056*
O1	0.2955 (3)	0.3828 (2)	0.0779 (2)	0.0566 (7)
O2	0.4926 (2)	0.1316 (2)	0.3521 (2)	0.0438 (6)
H2C	0.425 (4)	0.140 (4)	0.417 (3)	0.053*
O3	−0.0685 (3)	0.5958 (3)	0.2950 (3)	0.0810 (10)
O4	−0.2960 (3)	0.8831 (3)	0.4378 (2)	0.0559 (7)
H4A	−0.353 (4)	0.953 (5)	0.403 (4)	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0464 (18)	0.0401 (19)	0.059 (2)	−0.0115 (15)	−0.0050 (16)	−0.0090 (16)
C3	0.0375 (16)	0.0341 (17)	0.0389 (18)	−0.0084 (12)	0.0007 (13)	−0.0053 (13)
C4	0.0342 (15)	0.0366 (17)	0.0413 (18)	−0.0088 (13)	0.0014 (13)	−0.0057 (13)
C5	0.0436 (18)	0.049 (2)	0.049 (2)	−0.0146 (14)	−0.0096 (15)	−0.0024 (15)
C6	0.050 (2)	0.051 (2)	0.064 (2)	−0.0090 (16)	−0.0141 (17)	0.0053 (18)
C7	0.0366 (16)	0.0388 (18)	0.0426 (19)	−0.0143 (13)	−0.0018 (13)	−0.0076 (14)
C8	0.064 (2)	0.045 (2)	0.042 (2)	−0.0187 (16)	0.0001 (16)	−0.0069 (15)
C9	0.095 (3)	0.048 (2)	0.055 (2)	−0.029 (2)	−0.010 (2)	0.0034 (18)
C10	0.076 (3)	0.035 (2)	0.083 (3)	−0.0130 (18)	−0.022 (2)	−0.009 (2)
C11	0.065 (2)	0.050 (2)	0.066 (3)	−0.0073 (18)	−0.0044 (19)	−0.026 (2)
C12	0.056 (2)	0.046 (2)	0.047 (2)	−0.0150 (15)	0.0040 (16)	−0.0100 (16)
C13	0.056 (2)	0.037 (2)	0.095 (3)	−0.0165 (16)	−0.002 (2)	−0.0055 (19)
C14	0.0413 (17)	0.0396 (18)	0.052 (2)	−0.0101 (13)	0.0004 (15)	−0.0119 (15)
C15	0.0418 (17)	0.0336 (17)	0.0438 (18)	−0.0072 (13)	−0.0064 (14)	−0.0088 (13)
C16	0.0447 (19)	0.050 (2)	0.067 (3)	−0.0060 (15)	0.0054 (17)	−0.0224 (18)
C17	0.055 (2)	0.052 (2)	0.113 (4)	−0.0001 (18)	0.001 (2)	−0.035 (2)
C18	0.0340 (15)	0.0357 (17)	0.0380 (18)	−0.0086 (12)	0.0035 (13)	−0.0055 (13)
C19	0.0486 (19)	0.052 (2)	0.047 (2)	−0.0144 (16)	−0.0041 (15)	−0.0092 (16)
C20	0.048 (2)	0.062 (3)	0.054 (2)	−0.0064 (17)	−0.0054 (17)	0.0122 (19)
C21	0.058 (2)	0.035 (2)	0.075 (3)	−0.0101 (16)	0.011 (2)	0.0032 (19)
C22	0.074 (2)	0.041 (2)	0.067 (3)	−0.0227 (17)	0.009 (2)	−0.0174 (18)
C23	0.058 (2)	0.044 (2)	0.0385 (19)	−0.0157 (15)	−0.0005 (15)	−0.0083 (15)
O1	0.0590 (15)	0.0442 (14)	0.0606 (16)	−0.0161 (11)	−0.0118 (12)	0.0083 (11)
O2	0.0391 (12)	0.0488 (14)	0.0418 (14)	−0.0078 (10)	−0.0013 (10)	−0.0114 (10)
O3	0.0712 (19)	0.0453 (16)	0.136 (3)	−0.0162 (13)	0.0084 (18)	−0.0420 (17)
O4	0.0523 (14)	0.0467 (15)	0.0536 (16)	−0.0007 (11)	0.0081 (12)	0.0013 (12)

Geometric parameters (Å, º)

C2—O1	1.419 (4)	C13—C14	1.514 (5)
C2—C3	1.508 (4)	C13—H13A	0.9700
C2—H2A	0.9700	C13—H13B	0.9700
C2—H2B	0.9700	C14—O4	1.418 (4)
C3—O2	1.424 (4)	C14—C15	1.521 (4)
C3—C4	1.531 (4)	C14—H14	0.9800
C3—H3	0.9800	C15—C18	1.510 (4)
C4—C7	1.526 (4)	C15—C16	1.530 (4)
C4—C5	1.526 (4)	C15—H15	0.9800
C4—H4	0.9800	C16—C17	1.506 (5)
C5—C6	1.514 (5)	C16—H16A	0.9700
C5—H5A	0.9700	C16—H16B	0.9700
C5—H5B	0.9700	C17—O3	1.416 (5)
C6—O1	1.433 (4)	C17—H17A	0.9700
C6—H6A	0.9700	C17—H17B	0.9700
C6—H6B	0.9700	C18—C19	1.388 (4)
C7—C8	1.370 (4)	C18—C23	1.376 (5)
C7—C12	1.386 (4)	C19—C20	1.385 (5)
C8—C9	1.389 (5)	C19—H19	0.9300
C8—H8	0.9300	C20—C21	1.361 (6)
C9—C10	1.371 (6)	C20—H20	0.9300
C9—H9	0.9300	C21—C22	1.361 (6)
C10—C11	1.362 (6)	C21—H21	0.9300
C10—H10	0.9300	C22—C23	1.389 (5)
C11—C12	1.383 (5)	C22—H22	0.9300
C11—H11	0.9300	C23—H23	0.9300
C12—H12	0.9300	O2—H2C	0.91 (4)
C13—O3	1.420 (5)	O4—H4A	0.79 (4)
O1—C2—C3	112.9 (3)	C14—C13—H13A	109.3
O1—C2—H2A	109.0	O3—C13—H13B	109.3
C3—C2—H2A	109.0	C14—C13—H13B	109.3
O1—C2—H2B	109.0	H13A—C13—H13B	108.0
C3—C2—H2B	109.0	O4—C14—C15	111.8 (3)
H2A—C2—H2B	107.8	O4—C14—C13	107.7 (3)
O2—C3—C2	108.6 (3)	C15—C14—C13	110.5 (3)
O2—C3—C4	112.7 (2)	O4—C14—H14	109.0
C2—C3—C4	111.2 (2)	C15—C14—H14	109.0
O2—C3—H3	108.1	C13—C14—H14	109.0
C2—C3—H3	108.0	C18—C15—C16	113.9 (3)
C4—C3—H3	108.0	C18—C15—C14	113.0 (2)
C7—C4—C5	113.7 (3)	C16—C15—C14	109.0 (3)
C7—C4—C3	112.0 (2)	C18—C15—H15	106.8
C5—C4—C3	108.9 (2)	C16—C15—H15	106.8
C7—C4—H4	107.3	C14—C15—H15	106.8
C5—C4—H4	107.3	C17—C16—C15	110.8 (3)
C3—C4—H4	107.3	C17—C16—H16A	109.5
C6—C5—C4	111.0 (3)	C15—C16—H16A	109.5
C6—C5—H5A	109.5	C17—C16—H16B	109.5
C4—C5—H5A	109.4	C15—C16—H16B	109.5
C6—C5—H5B	109.4	H16A—C16—H16B	108.1
C4—C5—H5B	109.4	O3—C17—C16	112.1 (3)
H5A—C5—H5B	108.0	O3—C17—H17A	109.2
O1—C6—C5	111.3 (3)	C16—C17—H17A	109.2
O1—C6—H6A	109.4	O3—C17—H17B	109.2
C5—C6—H6A	109.4	C16—C17—H17B	109.2
O1—C6—H6B	109.4	H17A—C17—H17B	107.9
C5—C6—H6B	109.4	C19—C18—C23	117.6 (3)
H6A—C6—H6B	108.0	C19—C18—C15	122.3 (3)
C8—C7—C12	118.4 (3)	C23—C18—C15	120.1 (3)
C8—C7—C4	119.9 (3)	C18—C19—C20	120.6 (3)
C12—C7—C4	121.7 (3)	C18—C19—H19	119.7
C7—C8—C9	120.4 (3)	C20—C19—H19	119.7
C7—C8—H8	119.8	C21—C20—C19	120.7 (4)
C9—C8—H8	119.8	C21—C20—H20	119.6
C8—C9—C10	120.5 (4)	C19—C20—H20	119.6
C8—C9—H9	119.7	C22—C21—C20	119.7 (3)
C10—C9—H9	119.7	C22—C21—H21	120.2
C11—C10—C9	119.5 (4)	C20—C21—H21	120.2
C11—C10—H10	120.2	C21—C22—C23	120.0 (4)
C9—C10—H10	120.2	C21—C22—H22	120.0
C10—C11—C12	120.2 (4)	C23—C22—H22	120.0
C10—C11—H11	119.9	C22—C23—C18	121.4 (3)
C12—C11—H11	119.9	C22—C23—H23	119.3
C7—C12—C11	120.9 (3)	C18—C23—H23	119.3
C7—C12—H12	119.5	C2—O1—C6	110.5 (3)
C11—C12—H12	119.5	C3—O2—H2C	110 (2)
O3—C13—C14	111.4 (3)	C13—O3—C17	111.4 (3)
O3—C13—H13A	109.3	C14—O4—H4A	107 (3)
O1—C2—C3—O2	−179.9 (3)	O4—C14—C15—C18	−59.9 (4)
O1—C2—C3—C4	−55.3 (4)	C13—C14—C15—C18	−179.8 (3)
O2—C3—C4—C7	−60.8 (3)	O4—C14—C15—C16	172.4 (3)
C2—C3—C4—C7	176.9 (3)	C13—C14—C15—C16	52.5 (4)
O2—C3—C4—C5	172.6 (2)	C18—C15—C16—C17	−179.0 (3)
C2—C3—C4—C5	50.4 (3)	C14—C15—C16—C17	−51.7 (4)
C7—C4—C5—C6	−177.7 (3)	C15—C16—C17—O3	55.8 (5)
C3—C4—C5—C6	−52.0 (3)	C16—C15—C18—C19	54.8 (4)
C4—C5—C6—O1	58.0 (4)	C14—C15—C18—C19	−70.3 (4)
C5—C4—C7—C8	−134.2 (3)	C16—C15—C18—C23	−125.8 (3)
C3—C4—C7—C8	101.8 (3)	C14—C15—C18—C23	109.1 (3)
C5—C4—C7—C12	47.5 (4)	C23—C18—C19—C20	−0.5 (5)
C3—C4—C7—C12	−76.4 (4)	C15—C18—C19—C20	178.9 (3)
C12—C7—C8—C9	0.0 (5)	C18—C19—C20—C21	−0.3 (5)
C4—C7—C8—C9	−178.4 (3)	C19—C20—C21—C22	0.5 (6)
C7—C8—C9—C10	−0.2 (6)	C20—C21—C22—C23	0.1 (6)
C8—C9—C10—C11	0.4 (6)	C21—C22—C23—C18	−0.9 (5)
C9—C10—C11—C12	−0.4 (6)	C19—C18—C23—C22	1.1 (5)
C8—C7—C12—C11	0.1 (5)	C15—C18—C23—C22	−178.3 (3)
C4—C7—C12—C11	178.4 (3)	C3—C2—O1—C6	59.8 (4)
C10—C11—C12—C7	0.1 (6)	C5—C6—O1—C2	−60.8 (4)
O3—C13—C14—O4	−179.8 (3)	C14—C13—O3—C17	60.6 (4)
O3—C13—C14—C15	−57.5 (4)	C16—C17—O3—C13	−59.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···O4^i	0.91 (4)	1.92 (4)	2.823 (3)	168 (3)
O4—H4A···O2^ii	0.79 (4)	1.97 (4)	2.750 (3)	169 (4)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y+1, z.