5,5-Bis(hydroxy-meth-yl)-2-phenyl-1,3-dioxane.

In the title compound, C(12)H(16)O(4), the 1,3-dioxane ring adopts a chair conformation; the 2-phenyl substitutent occupies an equatorial position. Adjacent mol-ecules are linked by O-H⋯O hydrogen bonds into a chain.

Related literature

For the crystal structures of similar 5-aryl-1,3-dioxanes, see: Al-Mughaid et al. (2003 ▶); Grosu et al. (1997 ▶, 1998 ▶). For applications of this class of compounds, see: Wang et al. (1994 ▶); Yuan et al. (2005 ▶).

Experimental

Crystal data

C12H16O4

M = 224.25

Orthorhombic,

a = 6.2654 (4) Å

b = 10.4593 (6) Å

c = 34.5285 (19) Å

V = 2262.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 173 (2) K

0.46 × 0.42 × 0.21 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: none

5873 measured reflections

1403 independent reflections

1340 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.184

S = 1.14

1403 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022046/wn2272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022046/wn2272Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H16O4	F000 = 960
Mr = 224.25	Dx = 1.317 Mg m−3
Orthorhombic, C2221	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 4610 reflections
a = 6.2654 (4) Å	θ = 2.4–27.0º
b = 10.4593 (6) Å	µ = 0.10 mm−1
c = 34.5285 (19) Å	T = 173 (2) K
V = 2262.7 (2) Å3	Block, colorless
Z = 8	0.46 × 0.42 × 0.21 mm

Bruker SMART 1000 diffractometer	1340 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Monochromator: graphite	θmax = 27.0º
T = 173(2) K	θmin = 2.4º
φ and ω scans	h = −7→7
Absorption correction: None	k = −13→11
5873 measured reflections	l = −24→44
1403 independent 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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.184	w = 1/[σ2(Fo2) + (0.059P)2 + 10.1519P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
1403 reflections	Δρmax = 0.25 e Å−3
145 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
O1	0.8999 (6)	0.8806 (3)	0.63367 (9)	0.0263 (8)
O2	0.7606 (6)	0.6825 (3)	0.61705 (10)	0.0271 (8)
O3	0.3975 (7)	0.9308 (4)	0.71647 (11)	0.0410 (10)
H3O	0.4584	0.9956	0.7073	0.061*
O4	0.6297 (7)	0.6260 (4)	0.71881 (12)	0.0509 (12)
H4O	0.7073	0.5941	0.7361	0.076*
C1	0.8416 (8)	0.7994 (4)	0.60313 (13)	0.0223 (10)
H1	0.7304	0.8424	0.5869	0.027*
C2	1.0363 (7)	0.7728 (4)	0.57852 (12)	0.0216 (9)
C3	1.1598 (8)	0.8734 (5)	0.56544 (13)	0.0259 (10)
H3	1.1272	0.9583	0.5732	0.031*
C4	1.3332 (8)	0.8500 (5)	0.54074 (13)	0.0283 (11)
H4	1.4162	0.9193	0.5313	0.034*
C5	1.3830 (9)	0.7266 (5)	0.53020 (14)	0.0304 (11)
H5	1.5014	0.7107	0.5137	0.036*
C6	1.2612 (9)	0.6257 (5)	0.54353 (13)	0.0289 (10)
H6	1.2966	0.5406	0.5364	0.035*
C7	1.0871 (8)	0.6485 (4)	0.56740 (12)	0.0225 (10)
H7	1.0023	0.5791	0.5762	0.027*
C8	0.7140 (9)	0.9151 (4)	0.65602 (14)	0.0266 (11)
H8A	0.6150	0.9651	0.6396	0.032*
H8B	0.7578	0.9698	0.6780	0.032*
C9	0.5640 (8)	0.7038 (5)	0.63773 (14)	0.0282 (11)
H9A	0.5098	0.6214	0.6479	0.034*
H9B	0.4556	0.7391	0.6198	0.034*
C10	0.5989 (8)	0.7970 (4)	0.67141 (12)	0.0210 (9)
C11	0.3785 (8)	0.8368 (5)	0.68698 (14)	0.0287 (11)
H11A	0.2913	0.8713	0.6655	0.034*
H11B	0.3045	0.7608	0.6975	0.034*
C12	0.7350 (8)	0.7357 (5)	0.70299 (13)	0.0300 (11)
H12A	0.8744	0.7098	0.6920	0.036*
H12B	0.7618	0.7987	0.7238	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0287 (17)	0.0241 (16)	0.0261 (15)	−0.0100 (16)	0.0061 (15)	−0.0039 (13)
O2	0.0310 (18)	0.0194 (15)	0.0310 (16)	−0.0038 (16)	0.0109 (15)	−0.0052 (13)
O3	0.045 (2)	0.039 (2)	0.039 (2)	0.001 (2)	0.011 (2)	−0.0089 (17)
O4	0.046 (2)	0.057 (3)	0.049 (2)	0.018 (2)	0.018 (2)	0.031 (2)
C1	0.027 (2)	0.020 (2)	0.020 (2)	−0.002 (2)	0.0019 (18)	0.0012 (17)
C2	0.020 (2)	0.026 (2)	0.0188 (19)	0.0006 (19)	−0.0012 (17)	−0.0025 (18)
C3	0.032 (3)	0.025 (2)	0.0204 (19)	−0.001 (2)	0.000 (2)	−0.0016 (18)
C4	0.025 (2)	0.037 (3)	0.024 (2)	−0.008 (2)	0.0047 (19)	0.000 (2)
C5	0.024 (2)	0.042 (3)	0.025 (2)	0.000 (2)	0.006 (2)	−0.006 (2)
C6	0.031 (3)	0.030 (2)	0.025 (2)	0.003 (2)	0.000 (2)	−0.0081 (19)
C7	0.030 (2)	0.016 (2)	0.0219 (19)	−0.0002 (19)	0.000 (2)	0.0024 (16)
C8	0.038 (3)	0.0165 (19)	0.025 (2)	−0.006 (2)	0.007 (2)	−0.0024 (18)
C9	0.027 (3)	0.025 (2)	0.032 (2)	−0.009 (2)	0.008 (2)	−0.0056 (19)
C10	0.023 (2)	0.0186 (19)	0.0213 (19)	0.0015 (19)	0.0029 (18)	0.0017 (16)
C11	0.023 (2)	0.033 (3)	0.031 (2)	0.006 (2)	0.000 (2)	0.000 (2)
C12	0.025 (2)	0.042 (3)	0.023 (2)	0.014 (2)	0.004 (2)	0.006 (2)

O1—C1	1.403 (5)	C5—H5	0.9500
O1—C8	1.443 (6)	C6—C7	1.388 (7)
O2—C1	1.409 (5)	C6—H6	0.9500
O2—C9	1.441 (6)	C7—H7	0.9500
O3—C11	1.421 (6)	C8—C10	1.526 (6)
O3—H3O	0.8400	C8—H8A	0.9900
O4—C12	1.432 (7)	C8—H8B	0.9900
O4—H4O	0.8399	C9—C10	1.534 (6)
C1—C2	1.512 (6)	C9—H9A	0.9900
C1—H1	1.0000	C9—H9B	0.9900
C2—C3	1.382 (7)	C10—C12	1.526 (6)
C2—C7	1.392 (6)	C10—C11	1.539 (7)
C3—C4	1.403 (7)	C11—H11A	0.9900
C3—H3	0.9500	C11—H11B	0.9900
C4—C5	1.377 (7)	C12—H12A	0.9900
C4—H4	0.9500	C12—H12B	0.9900
C5—C6	1.381 (8)
C1—O1—C8	110.1 (4)	O1—C8—H8A	109.3
C1—O2—C9	110.1 (4)	C10—C8—H8A	109.3
C11—O3—H3O	109.0	O1—C8—H8B	109.3
C12—O4—H4O	108.9	C10—C8—H8B	109.3
O1—C1—O2	111.3 (3)	H8A—C8—H8B	108.0
O1—C1—C2	108.9 (4)	O2—C9—C10	110.6 (4)
O2—C1—C2	108.8 (4)	O2—C9—H9A	109.5
O1—C1—H1	109.3	C10—C9—H9A	109.5
O2—C1—H1	109.3	O2—C9—H9B	109.5
C2—C1—H1	109.3	C10—C9—H9B	109.5
C3—C2—C7	119.5 (4)	H9A—C9—H9B	108.1
C3—C2—C1	119.7 (4)	C8—C10—C12	109.0 (4)
C7—C2—C1	120.8 (4)	C8—C10—C9	108.6 (4)
C2—C3—C4	120.0 (5)	C12—C10—C9	110.7 (4)
C2—C3—H3	120.0	C8—C10—C11	109.1 (4)
C4—C3—H3	120.0	C12—C10—C11	111.4 (4)
C5—C4—C3	120.0 (5)	C9—C10—C11	108.0 (4)
C5—C4—H4	120.0	O3—C11—C10	111.3 (4)
C3—C4—H4	120.0	O3—C11—H11A	109.4
C4—C5—C6	120.2 (5)	C10—C11—H11A	109.4
C4—C5—H5	119.9	O3—C11—H11B	109.4
C6—C5—H5	119.9	C10—C11—H11B	109.4
C5—C6—C7	120.1 (5)	H11A—C11—H11B	108.0
C5—C6—H6	120.0	O4—C12—C10	110.6 (4)
C7—C6—H6	120.0	O4—C12—H12A	109.5
C6—C7—C2	120.3 (4)	C10—C12—H12A	109.5
C6—C7—H7	119.9	O4—C12—H12B	109.5
C2—C7—H7	119.9	C10—C12—H12B	109.5
O1—C8—C10	111.4 (4)	H12A—C12—H12B	108.1
C8—O1—C1—O2	−64.2 (5)	C1—C2—C7—C6	177.4 (4)
C8—O1—C1—C2	175.9 (4)	C1—O1—C8—C10	56.9 (5)
C9—O2—C1—O1	65.2 (5)	C1—O2—C9—C10	−58.0 (5)
C9—O2—C1—C2	−174.9 (4)	O1—C8—C10—C12	70.6 (5)
O1—C1—C2—C3	−50.6 (5)	O1—C8—C10—C9	−50.1 (5)
O2—C1—C2—C3	−172.1 (4)	O1—C8—C10—C11	−167.6 (4)
O1—C1—C2—C7	132.3 (4)	O2—C9—C10—C8	50.6 (5)
O2—C1—C2—C7	10.9 (6)	O2—C9—C10—C12	−69.0 (5)
C7—C2—C3—C4	0.8 (7)	O2—C9—C10—C11	168.7 (4)
C1—C2—C3—C4	−176.2 (4)	C8—C10—C11—O3	−57.8 (5)
C2—C3—C4—C5	−1.4 (7)	C12—C10—C11—O3	62.5 (5)
C3—C4—C5—C6	0.7 (8)	C9—C10—C11—O3	−175.6 (4)
C4—C5—C6—C7	0.5 (8)	C8—C10—C12—O4	178.6 (4)
C5—C6—C7—C2	−1.0 (7)	C9—C10—C12—O4	−62.0 (5)
C3—C2—C7—C6	0.3 (7)	C11—C10—C12—O4	58.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3i	0.84	2.19	2.644 (6)	114

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3i	0.84	2.19	2.644 (6)	114

Symmetry code: (i) .