3,5-Bis(2-hydroxy­ethyl)-4-oxahexa­cyclo­[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodeca­ne

The title mol­ecule, C₁₅H₂₀O₃, exhibits C—C bond lengths that deviate from normal values. A number of long and short C—C bonds are observed. Neighbouring mol­ecules inter­act via strong O—H...O hydrogen bonds, forming two-dimensional hydrogen-bonded sheets.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.049
• wR factor = 0.136
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL.

3,5-Bis(2-hydroxyethyl)-4- oxahexacyclo[5.4.1.0^2,6.0^3,10.0^5,9.0^8,11]dodecane

Crystal data

C15H20O3	F(000) = 536
Mr = 248.31	Dx = 1.352 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4355 reflections
a = 8.8011 (2) Å	θ = 2.3–29.7°
b = 19.8310 (4) Å	µ = 0.09 mm^−1
c = 7.0073 (1) Å	T = 173 K
β = 93.783 (1)°	Square, colourless
V = 1220.35 (4) Å^3	0.25 × 0.24 × 0.11 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2321 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 28.0°, θmin = 2.1°
φ and ω scans	h = −11→11
12806 measured reflections	k = −26→26
2942 independent reflections	l = −9→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0731P)^2 + 0.4354P] where P = (Fo^2 + 2Fc^2)/3
2942 reflections	(Δ/σ)max = 0.006
159 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.23 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
C11	0.08679 (15)	0.33644 (7)	0.72202 (19)	0.0179 (3)
C10	0.19858 (16)	0.36700 (7)	0.87720 (19)	0.0196 (3)
H10	0.2087	0.3404	0.9987	0.024*
C3	0.15670 (18)	0.44191 (7)	0.9043 (2)	0.0245 (3)
H3	0.0852	0.4512	1.0063	0.029*
C4	0.31124 (19)	0.47734 (8)	0.9293 (2)	0.0310 (4)
H4A	0.3712	0.4632	1.0470	0.037*
H4B	0.3023	0.5271	0.9251	0.037*
C5	0.37301 (17)	0.44799 (8)	0.7476 (2)	0.0264 (3)
H5	0.4787	0.4621	0.7215	0.032*
C9	0.34860 (16)	0.37126 (7)	0.7688 (2)	0.0211 (3)
H9	0.4371	0.3470	0.8341	0.025*
C8	0.29592 (15)	0.34187 (7)	0.5711 (2)	0.0187 (3)
C7	0.20257 (16)	0.40111 (7)	0.4802 (2)	0.0225 (3)
H71	0.1922	0.4037	0.3374	0.027*
C6	0.24827 (17)	0.46640 (7)	0.5911 (2)	0.0255 (3)
H6	0.2642	0.5080	0.5141	0.031*
C2	0.09865 (17)	0.46211 (7)	0.7000 (2)	0.0240 (3)
H2	0.0268	0.5011	0.6864	0.029*
C1	0.05390 (16)	0.39712 (7)	0.5874 (2)	0.0213 (3)
H1	−0.0450	0.3973	0.5084	0.026*
C12	−0.04944 (16)	0.29805 (7)	0.7844 (2)	0.0222 (3)
H12A	−0.0142	0.2570	0.8546	0.027*
H12B	−0.1131	0.2836	0.6699	0.027*
C13	−0.14481 (17)	0.34017 (8)	0.9111 (2)	0.0265 (3)
H13A	−0.0884	0.3478	1.0362	0.032*
H13B	−0.1664	0.3846	0.8508	0.032*
C14	0.41319 (17)	0.30822 (8)	0.4552 (2)	0.0238 (3)
H14A	0.3637	0.2936	0.3311	0.029*
H14B	0.4519	0.2674	0.5238	0.029*
C15	0.54663 (18)	0.35393 (8)	0.4183 (2)	0.0295 (4)
H15A	0.5081	0.3951	0.3515	0.035*
H15B	0.5978	0.3678	0.5422	0.035*
O1	0.18052 (11)	0.29321 (5)	0.61322 (14)	0.0202 (2)
O2	−0.28408 (12)	0.30596 (6)	0.93844 (16)	0.0313 (3)
H2A	−0.3108	0.3137	1.0493	0.047*
O3	0.65467 (14)	0.32159 (6)	0.30558 (18)	0.036
H3A	0.6771	0.2836	0.3526	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0161 (6)	0.0214 (6)	0.0167 (6)	0.0016 (5)	0.0046 (5)	−0.0008 (5)
C10	0.0189 (7)	0.0245 (7)	0.0156 (6)	−0.0002 (5)	0.0018 (5)	−0.0004 (5)
C3	0.0258 (7)	0.0260 (7)	0.0220 (7)	0.0013 (6)	0.0054 (6)	−0.0054 (6)
C4	0.0295 (8)	0.0310 (8)	0.0327 (9)	−0.0037 (7)	0.0032 (7)	−0.0091 (7)
C5	0.0209 (7)	0.0263 (7)	0.0325 (8)	−0.0051 (6)	0.0048 (6)	−0.0067 (6)
C9	0.0169 (6)	0.0253 (7)	0.0212 (7)	−0.0012 (5)	0.0018 (5)	−0.0022 (5)
C8	0.0167 (6)	0.0207 (6)	0.0193 (7)	−0.0014 (5)	0.0052 (5)	−0.0013 (5)
C7	0.0225 (7)	0.0269 (7)	0.0187 (7)	0.0010 (6)	0.0053 (6)	0.0026 (5)
C6	0.0276 (8)	0.0223 (7)	0.0273 (8)	0.0004 (6)	0.0076 (6)	0.0035 (6)
C2	0.0238 (7)	0.0206 (7)	0.0280 (8)	0.0043 (6)	0.0054 (6)	0.0021 (6)
C1	0.0199 (7)	0.0260 (7)	0.0183 (6)	0.0029 (5)	0.0027 (5)	0.0035 (5)
C12	0.0182 (7)	0.0253 (7)	0.0238 (7)	−0.0022 (5)	0.0057 (6)	−0.0004 (5)
C13	0.0207 (7)	0.0321 (8)	0.0277 (8)	−0.0023 (6)	0.0100 (6)	−0.0006 (6)
C14	0.0215 (7)	0.0256 (7)	0.0253 (7)	0.0004 (6)	0.0089 (6)	−0.0048 (6)
C15	0.0248 (8)	0.0322 (8)	0.0334 (9)	0.0006 (6)	0.0153 (7)	−0.0024 (6)
O1	0.0178 (5)	0.0206 (5)	0.0228 (5)	−0.0018 (4)	0.0071 (4)	−0.0040 (4)
O2	0.0201 (5)	0.0457 (7)	0.0293 (6)	−0.0057 (5)	0.0102 (5)	−0.0008 (5)
O3	0.032	0.042	0.036	0.005	0.022	0.003

Geometric parameters (Å, º)

C11—O1	1.4422 (16)	C7—C1	1.553 (2)
C11—C12	1.5090 (19)	C7—H71	1.0000
C11—C10	1.5416 (19)	C6—C2	1.567 (2)
C11—C1	1.5446 (19)	C6—H6	1.0000
C10—C3	1.545 (2)	C2—C1	1.548 (2)
C10—C9	1.568 (2)	C2—H2	1.0000
C10—H10	1.0000	C1—H1	1.0000
C3—C4	1.531 (2)	C12—C13	1.513 (2)
C3—C2	1.541 (2)	C12—H12A	0.9900
C3—H3	1.0000	C12—H12B	0.9900
C4—C5	1.532 (2)	C13—O2	1.4249 (18)
C4—H4A	0.9900	C13—H13A	0.9900
C4—H4B	0.9900	C13—H13B	0.9900
C5—C6	1.543 (2)	C14—C15	1.519 (2)
C5—C9	1.545 (2)	C14—H14A	0.9900
C5—H5	1.0000	C14—H14B	0.9900
C9—C8	1.5455 (19)	C15—O3	1.4277 (18)
C9—H9	1.0000	C15—H15A	0.9900
C8—O1	1.4456 (16)	C15—H15B	0.9900
C8—C14	1.5104 (19)	O2—H2A	0.8400
C8—C7	1.5467 (19)	O3—H3A	0.8400
C7—C6	1.549 (2)
O1—C11—C12	110.26 (11)	C1—C7—H71	117.5
O1—C11—C10	104.23 (10)	C5—C6—C7	107.92 (12)
C12—C11—C10	118.45 (11)	C5—C6—C2	102.85 (12)
O1—C11—C1	103.35 (10)	C7—C6—C2	90.01 (11)
C12—C11—C1	116.70 (12)	C5—C6—H6	117.4
C10—C11—C1	102.11 (11)	C7—C6—H6	117.4
C11—C10—C3	108.55 (11)	C2—C6—H6	117.4
C11—C10—C9	101.42 (10)	C3—C2—C1	108.34 (11)
C3—C10—C9	102.88 (11)	C3—C2—C6	103.22 (12)
C11—C10—H10	114.2	C1—C2—C6	89.47 (11)
C3—C10—H10	114.2	C3—C2—H2	117.3
C9—C10—H10	114.2	C1—C2—H2	117.3
C4—C3—C2	103.00 (13)	C6—C2—H2	117.3
C4—C3—C10	103.77 (12)	C11—C1—C2	107.82 (11)
C2—C3—C10	101.71 (11)	C11—C1—C7	101.84 (11)
C4—C3—H3	115.5	C2—C1—C7	90.57 (11)
C2—C3—H3	115.5	C11—C1—H1	117.5
C10—C3—H3	115.5	C2—C1—H1	117.5
C3—C4—C5	95.26 (12)	C7—C1—H1	117.5
C3—C4—H4A	112.7	C11—C12—C13	111.94 (12)
C5—C4—H4A	112.7	C11—C12—H12A	109.2
C3—C4—H4B	112.7	C13—C12—H12A	109.2
C5—C4—H4B	112.7	C11—C12—H12B	109.2
H4A—C4—H4B	110.2	C13—C12—H12B	109.2
C4—C5—C6	103.06 (13)	H12A—C12—H12B	107.9
C4—C5—C9	103.58 (12)	O2—C13—C12	109.35 (13)
C6—C5—C9	101.79 (11)	O2—C13—H13A	109.8
C4—C5—H5	115.5	C12—C13—H13A	109.8
C6—C5—H5	115.5	O2—C13—H13B	109.8
C9—C5—H5	115.5	C12—C13—H13B	109.8
C5—C9—C8	108.69 (12)	H13A—C13—H13B	108.3
C5—C9—C10	103.09 (11)	C8—C14—C15	113.03 (12)
C8—C9—C10	101.62 (10)	C8—C14—H14A	109.0
C5—C9—H9	114.1	C15—C14—H14A	109.0
C8—C9—H9	114.1	C8—C14—H14B	109.0
C10—C9—H9	114.1	C15—C14—H14B	109.0
O1—C8—C14	109.21 (11)	H14A—C14—H14B	107.8
O1—C8—C9	104.01 (11)	O3—C15—C14	112.13 (13)
C14—C8—C9	118.26 (12)	O3—C15—H15A	109.2
O1—C8—C7	103.29 (10)	C14—C15—H15A	109.2
C14—C8—C7	118.51 (12)	O3—C15—H15B	109.2
C9—C8—C7	101.70 (11)	C14—C15—H15B	109.2
C8—C7—C6	108.35 (11)	H15A—C15—H15B	107.9
C8—C7—C1	101.74 (11)	C11—O1—C8	98.34 (10)
C6—C7—C1	89.95 (11)	C13—O2—H2A	109.5
C8—C7—H71	117.5	C15—O3—H3A	109.5
C6—C7—H71	117.5
O1—C11—C10—C3	140.35 (11)	C1—C7—C6—C5	103.80 (12)
C12—C11—C10—C3	−96.71 (14)	C8—C7—C6—C2	−102.08 (12)
C1—C11—C10—C3	33.01 (14)	C1—C7—C6—C2	0.28 (11)
O1—C11—C10—C9	32.44 (13)	C4—C3—C2—C1	127.57 (13)
C12—C11—C10—C9	155.37 (12)	C10—C3—C2—C1	20.27 (15)
C1—C11—C10—C9	−74.91 (12)	C4—C3—C2—C6	33.67 (14)
C11—C10—C3—C4	−140.11 (12)	C10—C3—C2—C6	−73.62 (13)
C9—C10—C3—C4	−33.19 (14)	C5—C6—C2—C3	0.04 (14)
C11—C10—C3—C2	−33.42 (15)	C7—C6—C2—C3	108.44 (12)
C9—C10—C3—C2	73.50 (13)	C5—C6—C2—C1	−108.68 (12)
C2—C3—C4—C5	−53.28 (14)	C7—C6—C2—C1	−0.28 (11)
C10—C3—C4—C5	52.44 (14)	O1—C11—C1—C2	−127.07 (11)
C3—C4—C5—C6	53.38 (14)	C12—C11—C1—C2	111.75 (13)
C3—C4—C5—C9	−52.40 (14)	C10—C11—C1—C2	−19.05 (14)
C4—C5—C9—C8	140.55 (12)	O1—C11—C1—C7	−32.60 (13)
C6—C5—C9—C8	33.81 (15)	C12—C11—C1—C7	−153.78 (12)
C4—C5—C9—C10	33.28 (14)	C10—C11—C1—C7	75.43 (12)
C6—C5—C9—C10	−73.46 (13)	C3—C2—C1—C11	−0.84 (15)
C11—C10—C9—C5	112.19 (12)	C6—C2—C1—C11	102.92 (12)
C3—C10—C9—C5	−0.09 (13)	C3—C2—C1—C7	−103.48 (12)
C11—C10—C9—C8	−0.37 (13)	C6—C2—C1—C7	0.28 (11)
C3—C10—C9—C8	−112.65 (11)	C8—C7—C1—C11	0.10 (13)
C5—C9—C8—O1	−139.94 (11)	C6—C7—C1—C11	−108.64 (11)
C10—C9—C8—O1	−31.67 (13)	C8—C7—C1—C2	108.45 (11)
C5—C9—C8—C14	98.79 (15)	C6—C7—C1—C2	−0.29 (11)
C10—C9—C8—C14	−152.94 (12)	O1—C11—C12—C13	175.87 (11)
C5—C9—C8—C7	−32.87 (14)	C10—C11—C12—C13	56.00 (17)
C10—C9—C8—C7	75.41 (12)	C1—C11—C12—C13	−66.67 (16)
O1—C8—C7—C6	126.22 (11)	C11—C12—C13—O2	170.15 (12)
C14—C8—C7—C6	−112.92 (14)	O1—C8—C14—C15	−175.09 (12)
C9—C8—C7—C6	18.58 (14)	C9—C8—C14—C15	−56.52 (18)
O1—C8—C7—C1	32.32 (13)	C7—C8—C14—C15	67.12 (17)
C14—C8—C7—C1	153.18 (12)	C8—C14—C15—O3	−178.91 (13)
C9—C8—C7—C1	−75.32 (12)	C12—C11—O1—C8	178.96 (11)
C4—C5—C6—C7	−127.96 (12)	C10—C11—O1—C8	−52.90 (12)
C9—C5—C6—C7	−20.82 (15)	C1—C11—O1—C8	53.52 (12)
C4—C5—C6—C2	−33.72 (14)	C14—C8—O1—C11	179.60 (11)
C9—C5—C6—C2	73.42 (13)	C9—C8—O1—C11	52.47 (12)
C8—C7—C6—C5	1.44 (16)	C7—C8—O1—C11	−53.41 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3^i	0.84	1.85	2.6811 (16)	171
O3—H3A···O2^ii	0.84	1.90	2.7367 (17)	174

Symmetry codes: (i) x−1, y, z+1; (ii) x+1, −y+1/2, z−1/2.