Benzyl 5-hy­droxy-4-oxapenta­cyclo­[5.4.1.02,6.03,10.08,11]dodecane-3-carboxyl­ate

Karpoormath, R.; Naicker, T.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536811009020

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o877

doi:10.1107/S1600536811009020

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Benzyl 5-hydroxy-4-oxapentacyclo[5.4.1.0^2,6.0^3,10.0^8,11]dodecane-3-carboxylate

Rajshekhar Karpoormath,^a Tricia Naicker,^b Thavendran Govender,^b Hendrik G. Kruger ^a and Glenn E. M. Maguire ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, and ^bSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 16 February 2011; accepted 9 March 2011; online 12 March 2011)

The title compound, C₁₉H₁₈O₄, exhibits a long C—C bond [1.575 (2) Å] in the cage structure. In the crystal, pairs of O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. C—H⋯O interactions also occur.

Related literature

For examples of PCU cage structures that exhibit C—C bond lengths that deviate from the normal value, see: Flippen-Anderson et al. (1991); Linden et al. (2005 ). For similar structures, see: Kruger et al. (2005 , 2006 ); Karpoormath et al. (2010 ).

Experimental

Crystal data

C₁₉H₁₈O₄
M_r = 310.33
Monoclinic, P 2₁ /c
a = 6.5254 (2) Å
b = 12.8995 (2) Å
c = 16.9772 (5) Å
β = 95.243 (1)°
V = 1423.07 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.34 × 0.22 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer
6925 measured reflections
3540 independent reflections
2930 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.119
S = 1.06
3540 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.97 (2)	1.91 (2)	2.8561 (16)	164 (2)
C3—H3⋯O1ⁱⁱ	1.00	2.46	3.3716 (18)	151
C10—H10⋯O3ⁱⁱⁱ	1.00	2.41	3.3840 (19)	163
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, z; (iii) x+1, y, z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009020/is2678sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009020/is2678Isup2.hkl

checkCIF report

Comment top

We have reported the single-crystal X-ray structure of a range of pentacycloundecane (PCU) derivatives. More recently this included an ether diol (Kruger et al., 2005), a mono-ketone ethyl acetate (Kruger et al., 2006) and a mono-ketone diester (Karpoormath et al., 2010). The tile compound is the first example of a PCU derivative X-ray structure report containing an ether, ester and primary alcohol functional groups (Fig. 1). In the crystal, the ether oxygen hydrogen bonds to the primary alcohol group of its nearest neighbour (O1—H1···O2). This arrangement forms centrosymmetric dimers (Fig. 2).

Related literature top

For examples of PCU cage structures which exhibit C—C bond lengths that deviate from the normal value, see: Flippen-Anderson et al. (1991); Linden et al. (2005). For similar structures, see: Kruger et al. (2005, 2006); Karpoormath et al. (2010).

Experimental top

A mixture of 5-hydroxy-4 oxahexacyclo[5.4.0.0^2,6.0^3,10.0^5,9]dodecane-3-carboxylic acid (1 g, 4.5 mmol), benzyl bromide (6 ml, 4.95 mmol) and K₂CO₃ (1.86 g, 13.5 mmol) in DMF (5 ml), was heated to 120 °C and stirred for 5 h. The reaction mixture is cooled to room temperature and diluted with 50 ml of water and stirred further for 10 min. The resulting aqueous reaction mixture was then extracted with dichloromethane (25 ml × 2). The organic layer was dried with anhydrous Na₂SO₄, filtered, and concentrated under vacuum. Chromatography with hexane–EtOAc (5:1) afforded products a colourless oil (1.1 g, 79%). Crystallization of the product was carried out by dissolving the pure compound in 2 ml solvent mixture of ethyl acetate and hexane (1:5) and storing the solution at 18 °C (m.p. 397–398 K).

¹H NMR (CDCl₃, 400 MHz) δ p.p.m.: 1.55 (1.0H, d, J=10.69 Hz), 1.89 (1.0H, d, J=10.65 Hz), 2.59–2.67 (4.0H, m,), 2.73–2.77 (2.0H, m), 2.97–3.06 (2.0H, m), 4.20 (1.0H, s), 5.19 (2.0H, q, J=11.55 Hz), 7.28–7.33 (5.0H, m).

¹³C NMR (CDCl₃, 100 MHz) δ p.p.m.: 31.12, 42.10, 42.78, 43.44, 43.52, 46.66, 47.50, 49.88, 57.16, 59.31, 66.82, 89.89, 119.00, 128.24, 128.46, 128.75, 135.77, 171.32, 207.32.

IR (neat) V_max cm^-1: 3430.37, 2961.81, 1739.32, 1453.93, 1336.94, 1267.97, 1199.80, 1137.26, 1091.29, 1078.22, 902.84, 734.29, 692.33, 542.17 cm^-1.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the numbering scheme with ellipsoid probability of 50%.
	Fig. 2. Projection viewed along the [110] with ellipsoid probability of 40%. Only the hydrogen atoms involved in hydrogen bonds are shown. Other hydrogen atoms are omitted for clarity. The hydrogen bonds are shown as dotted lines.

Benzyl 5-hydroxy-4-oxapentacyclo[5.4.1.0^2,6.0^3,10.0^8,11]dodecane-3-carboxylate top

Crystal data top

C₁₉H₁₈O₄	F(000) = 656
M_r = 310.33	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6932 reflections
a = 6.5254 (2) Å	θ = 2.4–28.3°
b = 12.8995 (2) Å	µ = 0.10 mm⁻¹
c = 16.9772 (5) Å	T = 173 K
β = 95.243 (1)°	Block, colourless
V = 1423.07 (6) Å³	0.34 × 0.22 × 0.16 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2930 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 28.3°, θ_min = 3.1°
1.2° ϕ and ω scans	h = −8→8
6925 measured reflections	k = −17→17
3540 independent reflections	l = −22→22

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0463P)² + 0.932P] where P = (F_o² + 2F_c²)/3
3540 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.47 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₁₈O₄	V = 1423.07 (6) Å³
M_r = 310.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.5254 (2) Å	µ = 0.10 mm⁻¹
b = 12.8995 (2) Å	T = 173 K
c = 16.9772 (5) Å	0.34 × 0.22 × 0.16 mm
β = 95.243 (1)°

Data collection top

Nonius KappaCCD diffractometer	2930 reflections with I > 2σ(I)
6925 measured reflections	R_int = 0.018
3540 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.47 e Å⁻³
3540 reflections	Δρ_min = −0.24 e Å⁻³
212 parameters

Special details top

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 35 mm; combination of ϕ and ω scans of 1.2°, 30 s per °, 2 iterations.

X-ray single-crystal intensity data were collected on a Nonius Kappa-CCD diffractometer using graphite monochromated Mo K_α radiation (l = 0.71073 Å). Temperature was controlled by an Oxford Cryostream cooling system (Oxford Cryostat). The strategy for the data collections was evaluated using the Bruker Nonius "Collect" program (Nonius, 2000). Data were scaled and reduced using DENZO-SMN software (Otwinowski & Minor, 1997). The structure was solved by direct methods and refined employing full-matrix least-squares with the program SHELXL97 (Sheldrick, 2008) refining on F². The molecular graphics were rendered using OLEX2 (Dolomove et al., 2009). All non-hydrogen atoms were refined anisotropically.

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.74558 (16)	0.46393 (9)	0.05935 (6)	0.0284 (3)
H1	0.695 (4)	0.448 (2)	0.0053 (8)	0.073 (8)*
O2	0.45389 (15)	0.54964 (8)	0.09726 (6)	0.0223 (2)
O3	0.06298 (17)	0.60878 (9)	0.22148 (6)	0.0297 (3)
O4	0.10540 (16)	0.65377 (8)	0.09589 (6)	0.0260 (2)
C1	0.5554 (3)	0.33580 (14)	0.29940 (9)	0.0311 (4)
H1A	0.6449	0.3717	0.3411	0.037*
H1B	0.5203	0.2656	0.3174	0.037*
C2	0.2721 (2)	0.33660 (12)	0.19839 (9)	0.0279 (3)
H2	0.1596	0.2865	0.2073	0.034*
C3	0.2365 (2)	0.41085 (12)	0.12688 (9)	0.0246 (3)
H3	0.1021	0.4065	0.0937	0.029*
C4	0.3155 (2)	0.52032 (11)	0.15444 (8)	0.0208 (3)
C5	0.4540 (2)	0.49471 (12)	0.23047 (9)	0.0244 (3)
H5	0.4826	0.5553	0.2666	0.029*
C6	0.3646 (2)	0.39964 (13)	0.27044 (9)	0.0276 (3)
H6	0.2680	0.4154	0.3113	0.033*
C7	0.4690 (2)	0.29226 (12)	0.16299 (9)	0.0278 (3)
H7	0.4703	0.2164	0.1510	0.033*
C8	0.4308 (2)	0.36722 (12)	0.09197 (9)	0.0250 (3)
H8	0.4127	0.3363	0.0378	0.030*
C9	0.5850 (2)	0.45678 (11)	0.10606 (8)	0.0213 (3)
C10	0.6490 (2)	0.45031 (12)	0.19510 (8)	0.0241 (3)
H10	0.7798	0.4876	0.2125	0.029*
C11	0.6469 (2)	0.33477 (13)	0.21925 (9)	0.0284 (3)
H11	0.7810	0.2975	0.2183	0.034*
C12	0.1500 (2)	0.59911 (11)	0.16209 (8)	0.0226 (3)
C13	−0.0640 (2)	0.72567 (13)	0.09816 (9)	0.0286 (3)
H13A	−0.0465	0.7671	0.1474	0.034*
H13B	−0.1952	0.6870	0.0976	0.034*
C14	−0.0697 (2)	0.79630 (12)	0.02758 (9)	0.0250 (3)
C15	0.0895 (3)	0.80217 (13)	−0.02124 (10)	0.0309 (4)
H15	0.2077	0.7596	−0.0111	0.037*
C16	0.0759 (3)	0.87050 (14)	−0.08503 (10)	0.0350 (4)
H16	0.1843	0.8737	−0.1187	0.042*
C17	−0.0945 (3)	0.93378 (14)	−0.09964 (10)	0.0347 (4)
H17	−0.1025	0.9807	−0.1429	0.042*
C18	−0.2529 (3)	0.92858 (13)	−0.05118 (10)	0.0336 (4)
H18	−0.3697	0.9722	−0.0610	0.040*
C19	−0.2416 (3)	0.85979 (13)	0.01181 (10)	0.0296 (3)
H19	−0.3520	0.8559	0.0445	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0213 (5)	0.0420 (7)	0.0227 (5)	0.0026 (5)	0.0060 (4)	0.0028 (5)
O2	0.0218 (5)	0.0248 (5)	0.0209 (5)	0.0011 (4)	0.0052 (4)	0.0030 (4)
O3	0.0329 (6)	0.0344 (6)	0.0232 (5)	0.0061 (5)	0.0094 (4)	0.0017 (4)
O4	0.0295 (6)	0.0265 (5)	0.0225 (5)	0.0075 (4)	0.0054 (4)	0.0035 (4)
C1	0.0347 (8)	0.0332 (9)	0.0252 (8)	0.0010 (7)	0.0016 (6)	0.0059 (6)
C2	0.0250 (7)	0.0262 (8)	0.0328 (8)	−0.0035 (6)	0.0032 (6)	0.0046 (6)
C3	0.0198 (7)	0.0242 (7)	0.0294 (8)	−0.0018 (6)	0.0010 (6)	−0.0003 (6)
C4	0.0203 (6)	0.0243 (7)	0.0183 (6)	−0.0006 (5)	0.0045 (5)	0.0019 (5)
C5	0.0253 (7)	0.0283 (8)	0.0197 (7)	0.0000 (6)	0.0020 (5)	−0.0005 (6)
C6	0.0307 (8)	0.0303 (8)	0.0227 (7)	0.0045 (6)	0.0071 (6)	0.0054 (6)
C7	0.0303 (8)	0.0230 (7)	0.0304 (8)	0.0009 (6)	0.0042 (6)	0.0002 (6)
C8	0.0230 (7)	0.0248 (7)	0.0269 (7)	0.0018 (6)	−0.0002 (6)	−0.0027 (6)
C9	0.0188 (6)	0.0254 (7)	0.0200 (7)	0.0020 (5)	0.0025 (5)	0.0013 (5)
C10	0.0206 (7)	0.0309 (8)	0.0205 (7)	−0.0015 (6)	0.0005 (5)	0.0013 (6)
C11	0.0253 (7)	0.0331 (8)	0.0263 (8)	0.0033 (6)	−0.0002 (6)	0.0058 (6)
C12	0.0240 (7)	0.0227 (7)	0.0211 (7)	−0.0022 (5)	0.0021 (5)	0.0004 (5)
C13	0.0293 (8)	0.0292 (8)	0.0278 (8)	0.0089 (6)	0.0061 (6)	0.0030 (6)
C14	0.0298 (8)	0.0223 (7)	0.0224 (7)	0.0014 (6)	0.0001 (6)	−0.0028 (6)
C15	0.0325 (8)	0.0296 (8)	0.0310 (8)	0.0041 (7)	0.0047 (7)	0.0038 (6)
C16	0.0420 (10)	0.0348 (9)	0.0290 (8)	0.0017 (7)	0.0077 (7)	0.0036 (7)
C17	0.0498 (10)	0.0285 (8)	0.0250 (8)	0.0022 (7)	−0.0008 (7)	0.0035 (6)
C18	0.0402 (9)	0.0291 (8)	0.0305 (8)	0.0082 (7)	−0.0030 (7)	0.0000 (7)
C19	0.0318 (8)	0.0291 (8)	0.0277 (8)	0.0048 (6)	0.0024 (6)	−0.0019 (6)

Geometric parameters (Å, º) top

O1—C9	1.3740 (17)	C7—C11	1.536 (2)
O1—H1	0.969 (10)	C7—C8	1.548 (2)
O2—C4	1.4355 (16)	C7—H7	1.0000
O2—C9	1.4715 (17)	C8—C9	1.536 (2)
O3—C12	1.2081 (18)	C8—H8	1.0000
O4—C12	1.3362 (18)	C9—C10	1.533 (2)
O4—C13	1.4463 (18)	C10—C11	1.546 (2)
C1—C11	1.535 (2)	C10—H10	1.0000
C1—C6	1.536 (2)	C11—H11	1.0000
C1—H1A	0.9900	C13—C14	1.503 (2)
C1—H1B	0.9900	C13—H13A	0.9900
C2—C6	1.545 (2)	C13—H13B	0.9900
C2—C3	1.547 (2)	C14—C15	1.389 (2)
C2—C7	1.575 (2)	C14—C19	1.395 (2)
C2—H2	1.0000	C15—C16	1.393 (2)
C3—C8	1.553 (2)	C15—H15	0.9500
C3—C4	1.560 (2)	C16—C17	1.384 (3)
C3—H3	1.0000	C16—H16	0.9500
C4—C12	1.497 (2)	C17—C18	1.380 (3)
C4—C5	1.542 (2)	C17—H17	0.9500
C5—C6	1.542 (2)	C18—C19	1.386 (2)
C5—C10	1.565 (2)	C18—H18	0.9500
C5—H5	1.0000	C19—H19	0.9500
C6—H6	1.0000

C9—O1—H1	108.6 (16)	C9—C8—H8	117.7
C4—O2—C9	96.46 (10)	C7—C8—H8	117.7
C12—O4—C13	115.11 (11)	C3—C8—H8	117.7
C11—C1—C6	95.19 (12)	O1—C9—O2	110.72 (11)
C11—C1—H1A	112.7	O1—C9—C10	114.78 (12)
C6—C1—H1A	112.7	O2—C9—C10	104.35 (11)
C11—C1—H1B	112.7	O1—C9—C8	118.94 (12)
C6—C1—H1B	112.7	O2—C9—C8	103.29 (11)
H1A—C1—H1B	110.2	C10—C9—C8	103.19 (12)
C6—C2—C3	108.38 (13)	C9—C10—C11	107.80 (12)
C6—C2—C7	102.71 (12)	C9—C10—C5	101.56 (11)
C3—C2—C7	89.69 (11)	C11—C10—C5	102.95 (12)
C6—C2—H2	117.3	C9—C10—H10	114.4
C3—C2—H2	117.3	C11—C10—H10	114.4
C7—C2—H2	117.3	C5—C10—H10	114.4
C2—C3—C8	90.34 (11)	C1—C11—C7	102.77 (13)
C2—C3—C4	107.64 (12)	C1—C11—C10	103.90 (13)
C8—C3—C4	100.58 (11)	C7—C11—C10	101.75 (12)
C2—C3—H3	118.0	C1—C11—H11	115.5
C8—C3—H3	118.0	C7—C11—H11	115.5
C4—C3—H3	118.0	C10—C11—H11	115.5
O2—C4—C12	112.52 (11)	O3—C12—O4	124.37 (14)
O2—C4—C5	105.42 (11)	O3—C12—C4	122.71 (13)
C12—C4—C5	116.41 (12)	O4—C12—C4	112.88 (12)
O2—C4—C3	104.28 (11)	O4—C13—C14	109.31 (12)
C12—C4—C3	114.78 (12)	O4—C13—H13A	109.8
C5—C4—C3	102.09 (12)	C14—C13—H13A	109.8
C6—C5—C4	108.82 (12)	O4—C13—H13B	109.8
C6—C5—C10	103.38 (12)	C14—C13—H13B	109.8
C4—C5—C10	101.08 (11)	H13A—C13—H13B	108.3
C6—C5—H5	114.1	C15—C14—C19	119.06 (15)
C4—C5—H5	114.1	C15—C14—C13	122.93 (14)
C10—C5—H5	114.1	C19—C14—C13	118.01 (14)
C1—C6—C5	103.84 (12)	C14—C15—C16	120.05 (16)
C1—C6—C2	102.58 (13)	C14—C15—H15	120.0
C5—C6—C2	101.90 (12)	C16—C15—H15	120.0
C1—C6—H6	115.5	C17—C16—C15	120.37 (16)
C5—C6—H6	115.5	C17—C16—H16	119.8
C2—C6—H6	115.5	C15—C16—H16	119.8
C11—C7—C8	108.68 (13)	C18—C17—C16	119.86 (16)
C11—C7—C2	103.28 (12)	C18—C17—H17	120.1
C8—C7—C2	89.51 (11)	C16—C17—H17	120.1
C11—C7—H7	117.1	C17—C18—C19	120.08 (16)
C8—C7—H7	117.1	C17—C18—H18	120.0
C2—C7—H7	117.1	C19—C18—H18	120.0
C9—C8—C7	106.97 (12)	C18—C19—C14	120.57 (16)
C9—C8—C3	102.35 (11)	C18—C19—H19	119.7
C7—C8—C3	90.47 (11)	C14—C19—H19	119.7

C6—C2—C3—C8	103.26 (13)	C3—C8—C9—O1	−156.62 (12)
C7—C2—C3—C8	−0.05 (11)	C7—C8—C9—O2	−127.86 (12)
C6—C2—C3—C4	2.05 (16)	C3—C8—C9—O2	−33.53 (13)
C7—C2—C3—C4	−101.26 (12)	C7—C8—C9—C10	−19.38 (14)
C9—O2—C4—C12	−179.39 (12)	C3—C8—C9—C10	74.95 (13)
C9—O2—C4—C5	52.74 (13)	O1—C9—C10—C11	−97.66 (15)
C9—O2—C4—C3	−54.38 (12)	O2—C9—C10—C11	140.99 (12)
C2—C3—C4—O2	127.36 (12)	C8—C9—C10—C11	33.31 (14)
C8—C3—C4—O2	33.59 (13)	O1—C9—C10—C5	154.53 (13)
C2—C3—C4—C12	−109.09 (14)	O2—C9—C10—C5	33.17 (14)
C8—C3—C4—C12	157.15 (12)	C8—C9—C10—C5	−74.51 (13)
C2—C3—C4—C5	17.78 (14)	C6—C5—C10—C9	111.60 (13)
C8—C3—C4—C5	−75.99 (13)	C4—C5—C10—C9	−1.00 (14)
O2—C4—C5—C6	−140.89 (12)	C6—C5—C10—C11	0.06 (14)
C12—C4—C5—C6	93.62 (15)	C4—C5—C10—C11	−112.55 (12)
C3—C4—C5—C6	−32.18 (14)	C6—C1—C11—C7	−53.88 (14)
O2—C4—C5—C10	−32.49 (14)	C6—C1—C11—C10	51.86 (14)
C12—C4—C5—C10	−157.98 (12)	C8—C7—C11—C1	127.80 (13)
C3—C4—C5—C10	76.22 (13)	C2—C7—C11—C1	33.76 (15)
C11—C1—C6—C5	−51.77 (14)	C8—C7—C11—C10	20.41 (15)
C11—C1—C6—C2	54.05 (14)	C2—C7—C11—C10	−73.63 (14)
C4—C5—C6—C1	139.75 (13)	C9—C10—C11—C1	−139.89 (12)
C10—C5—C6—C1	32.92 (14)	C5—C10—C11—C1	−33.04 (14)
C4—C5—C6—C2	33.42 (15)	C9—C10—C11—C7	−33.39 (15)
C10—C5—C6—C2	−73.42 (13)	C5—C10—C11—C7	73.46 (13)
C3—C2—C6—C1	−128.27 (13)	C13—O4—C12—O3	−2.0 (2)
C7—C2—C6—C1	−34.31 (14)	C13—O4—C12—C4	175.61 (12)
C3—C2—C6—C5	−20.96 (15)	O2—C4—C12—O3	−154.75 (14)
C7—C2—C6—C5	73.00 (14)	C5—C4—C12—O3	−32.9 (2)
C6—C2—C7—C11	0.35 (15)	C3—C4—C12—O3	86.21 (18)
C3—C2—C7—C11	109.13 (12)	O2—C4—C12—O4	27.56 (17)
C6—C2—C7—C8	−108.74 (12)	C5—C4—C12—O4	149.38 (13)
C3—C2—C7—C8	0.05 (11)	C3—C4—C12—O4	−91.48 (15)
C11—C7—C8—C9	−0.84 (16)	C12—O4—C13—C14	168.61 (13)
C2—C7—C8—C9	103.02 (12)	O4—C13—C14—C15	−11.6 (2)
C11—C7—C8—C3	−103.91 (13)	O4—C13—C14—C19	169.54 (13)
C2—C7—C8—C3	−0.05 (11)	C19—C14—C15—C16	−0.2 (2)
C2—C3—C8—C9	−107.44 (12)	C13—C14—C15—C16	−178.99 (16)
C4—C3—C8—C9	0.58 (14)	C14—C15—C16—C17	0.8 (3)
C2—C3—C8—C7	0.05 (12)	C15—C16—C17—C18	−0.6 (3)
C4—C3—C8—C7	108.07 (12)	C16—C17—C18—C19	−0.3 (3)
C4—O2—C9—O1	−177.16 (11)	C17—C18—C19—C14	0.9 (3)
C4—O2—C9—C10	−53.15 (12)	C15—C14—C19—C18	−0.6 (2)
C4—O2—C9—C8	54.46 (12)	C13—C14—C19—C18	178.21 (15)
C7—C8—C9—O1	109.05 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.97 (2)	1.91 (2)	2.8561 (16)	164 (2)
C3—H3···O1ⁱⁱ	1.00	2.46	3.3716 (18)	151
C10—H10···O3ⁱⁱⁱ	1.00	2.41	3.3840 (19)	163

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O₄
M_r	310.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.5254 (2), 12.8995 (2), 16.9772 (5)
β (°)	95.243 (1)
V (Å³)	1423.07 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.22 × 0.16

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6925, 3540, 2930
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.119, 1.06
No. of reflections	3540
No. of parameters	212
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.24

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.972 (15)	1.910 (17)	2.8561 (16)	164 (2)
C3—H3···O1ⁱⁱ	1.00	2.46	3.3716 (18)	151
C10—H10···O3ⁱⁱⁱ	1.00	2.41	3.3840 (19)	163

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

Acknowledgements

The authors would like to thank Dr Hong Su from the University of Capetown for the data collection and structure refinement.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flippen-Anderson, J. L., George, C., Gilardi, R., Zajac, W. W., Walters, T. R., Marchand, A., Dave, P. R. & Arney, B. E. (1991). Acta Cryst. C47, 813–817. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Karpoormath, R., Govender, T., Govender, P., Kruger, H. G. & Maguire, G. E. M. (2010). Acta Cryst. E66, o2607–o2608. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kruger, H. G., Rademeyer, M. & Ramdhani, R. (2005). Acta Cryst. E61, o3968–o3970. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kruger, H. G., Rademeyer, M. & Ramdhani, R. (2006). Acta Cryst. E62, o268–o270. Web of Science CSD CrossRef IUCr Journals Google Scholar
Linden, A., Romański, J., Mlostoń, G. & Heimgartner, H. (2005). Acta Cryst. C61, o221–o226. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Benzyl 5-hy­dr­oxy-4-oxa­penta­cyclo­[5.4.1.02,6.03,10.08,11]do­decane-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Benzyl 5-hydroxy-4-oxapentacyclo[5.4.1.0^2,6.0^3,10.0^8,11]dodecane-3-carboxylate