(1′S,6′S,8′S,9′R)-9′-Bromo-12′-oxa­spiro­[1,3-dioxolane-2,4′-tricyclo­[6.3.1.01,6]dodeca­ne]

Mehta, G.; Khan, T.B.

doi:10.1107/S1600536812029777

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2411-o2412

https://doi.org/10.1107/S1600536812029777

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(1′S,6′S,8′S,9′R)-9′-Bromo-12′-oxaspiro[1,3-dioxolane-2,4′-tricyclo[6.3.1.0^1,6]dodecane]

Goverdhan Mehta ^a,^b ^* and Tabrez Babu Khan ^a,^b

^aDepartment of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^bSchool of Chemistry, University of Hyderabad, Hyderabad 500 046, A.P. India
^*Correspondence e-mail: gmsc@uohyd.ernet.in, gm@orgchem.iisc.ernet.in

(Received 15 June 2012; accepted 29 June 2012; online 10 July 2012)

In an endeavor directed towards the construction of the oxabicyclic[3.2.1]octane segment present in the bioactive natural products of cortistatins and icetexanes genre, the title compound, C₁₃H₁₉BrO₃, was synthesized from (4aR,9aS)-1,3,4,4a,5,6,9,9a-octahydrospiro[benzo[7]annulene-2,2′-[1,3]dioxolane]-4a-ol via a transannular bromo-etherification protocol. The six-membered ring adopts a twist-boat conformation, while the fused cycloheptane ring adopts a chair conformation. The crystal packing is effected through two distinct intermolecular C—H⋯O hydrogen-bond patterns and molecules are arranged to define an interesting motif along the b axis.

Related literature

For the isolation and biological activity of cortistatins, see: Aoki et al. (2006 , 2007 ); Watanabe et al. (2007 ); Zhao (2010 ) and for icetexanes, see: Esquivel et al. (1995 ); Uchiyama et al. (2005 ). For synthetic approaches towards the construction of the oxabicyclic core of cortistatins, see: Zhao (2010); Hardin Narayan et al. (2010 ) and references cited therein. For their use in the treatment of blindness, see: Czako et al. (2009 ). For the construction of relevant 6/7 fused-ring systems involving ring-closing metathesis, see: Mehta & Likhite (2008 , 2009 ). For an example of the exploitation of transannular bromoetherification towards natural products synthesis, see: Mehta & Sen (2010 ); Mehta & Yaragorla (2011 ).

Experimental

Crystal data

C₁₃H₁₉BrO₃
M_r = 303.19
Monoclinic, P 2₁ /c
a = 11.0159 (3) Å
b = 12.6619 (3) Å
c = 10.2763 (2) Å
β = 117.044 (1)°
V = 1276.63 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.21 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.446, T_max = 0.644
11338 measured reflections
2368 independent reflections
1859 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.076
S = 1.02
2368 reflections
154 parameters
?
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.98	2.53	3.445 (3)	156
C1—H1⋯O1ⁱⁱ	0.98	2.57	3.471 (3)	153
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029777/ds2204sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029777/ds2204Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029777/ds2204Isup3.cml

checkCIF report

Comment top

The oxabicyclic[3,2,1]octane scaffold manifest itself in a variety of terpenoids class of natural products viz. icetexanes (Fig. 1; Esquivel et al., 1995 & Uchiyama et al., 2005) and cortistatin family (Fig. 1; Aoki et al., 2006, 2007 & Watanabe et al., 2007). In particular, cortistatin A and its structural siblings isolated in trace amounts by Kobayashi & coworkers from an Indonesian marine sponge corticium simplex were shown to possess novel architecture and exhibited potent and promising anti-angiogenic activity (Zhao, 2010) and were effective in treating blindness (Czako et al., 2009), thereby triggering interest to devise tactics for their total synthesis and diversity creation. These attributes of cortistatins encouraged us to devise a strategy to gain rapid access to the oxatricyclic ABC core present in cortistatins.

Several synthetic approaches to cortistatins have been reported utilizing ring-expansion approach, oxidative dearomatization, electrocyclization, 1,3-dipolar cycloaddition/electrocyclization cascade, transannular [4 + 3] cycloaddition, classical Michael/aldol condensation cascade cyclization as the key strategic steps to access the oxatricyclic segment (Hardin Narayan et al., 2010). However, the present strategy employs a stepwise transannular bromoetherification sequence (Mehta & Sen, 2010; Mehta & Yaragorla, 2011) on a readily accessible bicyclic compound obtained via RCM (Fig. 2; Mehta & Likhite, 2008, 2009).

A two step transannular bromoetherification protocol on 7 furnished the title compound 3 (Fig. 2) as the major product corresponding to the oxatricyclic core present in icetexanes along with a minor regioisomeric compound 4 representing the oxatricyclic segment present in cortistatins.

The title compound 3 was crystallized from ethylacetate-hexane(1:1) and the structure was solved and refined in monoclinic P2₁/c space group with one molecule of 3 in the asymmetric unit. An ORTEP diagram of 3 drawn at 30% ellipsoidal probability is depicted in Fig 3. From the packing diagram it can be seen that the centrosymmetric molecules are connected by weak C11–H11···O2 (2.53 Å, 156°) hydrogen bonds forming a dimeric motif and these dimeric units are further connected by C1–H1···O1 (2.57 Å, 153°)) hydrogen bonds, three dimensionally (Fig. 4).These two hydrogen bond patterns link the molecules to define an interesting motif along the b axis.

Related literature top

For the isolation and biological activity of cortistatins, see: Aoki et al. (2006, 2007); Watanabe et al. (2007); Zhao (2010) and for icetexanes, see: Esquivel et al. (1995); Uchiyama et al. (2005). For synthetic approaches towards the construction of the oxabicyclic core of cortistatins, see: Zhao (2010); Hardin Narayan et al. (2010) and references cited therein. For their use in the treatment of blindness, see: Czako et al. (2009). For the construction of relevant 6/7 fused-ring systems involving ring-closing metathesis, see: Mehta & Likhite (2008, 2009). For an example of the exploitation of transannular bromoetherification towards natural products synthesis, see: Mehta & Sen (2010); Mehta & Yaragorla (2011).

Experimental top

The synthesis of the title compound 3 as depicted in Fig. 2 emanates from the known 7-(prop-2-en-1-yl)-1,4-dioxaspiro[4.5]decan-8-one 5 through addition of butenylmagnesium bromide (1.5 equiv.) in THF at r.t. to furnish the desired RCM precursor 6 in decent yield. Exposure of 6 to Grubbs-1s t generation catalyst (10 mol%) in benzene at r.t. gave the bicyclic compound 7 in good yield. Finally, the stepwise transannular bromotherification on 7 was executed via bromination with pyH⁺Br₃^- (1.2 equiv.) in DCM at 0 °C followed by etherification in the presence of 10 M aq. NaOH in THF at 60 °C for 4 h to deliver 3, mp. 78–80 °C, as a colorless crystalline compound in 51% yield.

Structure description top

For the isolation and biological activity of cortistatins, see: Aoki et al. (2006, 2007); Watanabe et al. (2007); Zhao (2010) and for icetexanes, see: Esquivel et al. (1995); Uchiyama et al. (2005). For synthetic approaches towards the construction of the oxabicyclic core of cortistatins, see: Zhao (2010); Hardin Narayan et al. (2010) and references cited therein. For their use in the treatment of blindness, see: Czako et al. (2009). For the construction of relevant 6/7 fused-ring systems involving ring-closing metathesis, see: Mehta & Likhite (2008, 2009). For an example of the exploitation of transannular bromoetherification towards natural products synthesis, see: Mehta & Sen (2010); Mehta & Yaragorla (2011).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Representative example of cortistatin family (cortistatin A 1) & icetexane family (salviasperanol 2).
	Fig. 2. The synthesis of the title compound.
	Fig. 3. The molecular structure of the title compound 3, with the atom numbering scheme. Dispalcement ellipsoids for non-H atoms are drawn at 30% probability.
	Fig. 4. A packing diagram of the title compound 3, viewed along the b axis. Dotted lines indicate the C—H···O hydrogen bonds.

(1'S,6'S,8'S,9'R)-9'-Bromo-12'-oxaspiro[1,3- dioxolane-2,4'-tricyclo[6.3.1.0^1,6]dodecane] top

Crystal data top

C₁₃H₁₉BrO₃	F(000) = 624
M_r = 303.19	D_x = 1.577 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4277 reflections
a = 11.0159 (3) Å	θ = 2.6–24.2°
b = 12.6619 (3) Å	µ = 3.21 mm⁻¹
c = 10.2763 (2) Å	T = 296 K
β = 117.044 (1)°	Block, colorless
V = 1276.63 (5) Å³	0.30 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2368 independent reflections
Radiation source: fine-focus sealed tube	1859 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 25.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→12
T_min = 0.446, T_max = 0.644	k = −15→14
11338 measured reflections	l = −9→12

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0436P)² + 0.2892P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
2368 reflections	Δρ_max = 0.25 e Å⁻³
154 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints

Crystal data top

C₁₃H₁₉BrO₃	V = 1276.63 (5) Å³
M_r = 303.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0159 (3) Å	µ = 3.21 mm⁻¹
b = 12.6619 (3) Å	T = 296 K
c = 10.2763 (2) Å	0.30 × 0.20 × 0.15 mm
β = 117.044 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2368 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1859 reflections with I > 2σ(I)
T_min = 0.446, T_max = 0.644	R_int = 0.027
11338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	154 parameters
wR(F²) = 0.076	0 restraints
S = 1.02	Δρ_max = 0.25 e Å⁻³
2368 reflections	Δρ_min = −0.32 e Å⁻³

Special details top

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
Br1	0.70444 (3)	0.11259 (2)	0.71170 (3)	0.06222 (13)
O1	0.66345 (15)	0.35583 (12)	0.61783 (15)	0.0391 (4)
O2	0.7122 (2)	0.73040 (14)	0.57865 (18)	0.0640 (5)
O3	0.84162 (18)	0.72842 (13)	0.82550 (18)	0.0529 (4)
C1	0.6947 (2)	0.24005 (18)	0.8181 (2)	0.0424 (5)
H1	0.6541	0.2205	0.8820	0.051*
C11	0.6034 (2)	0.32101 (18)	0.7079 (2)	0.0404 (5)
H11	0.5125	0.2915	0.6480	0.048*
C13	0.7789 (3)	0.8290 (2)	0.7886 (3)	0.0547 (7)
H13A	0.8441	0.8848	0.8377	0.066*
H13B	0.7043	0.8344	0.8138	0.066*
C4	0.7757 (2)	0.42229 (17)	0.7136 (2)	0.0348 (5)
C2	0.8358 (2)	0.2838 (2)	0.9109 (3)	0.0479 (6)
H2A	0.8985	0.2259	0.9566	0.057*
H2B	0.8345	0.3275	0.9878	0.057*
C7	0.7737 (2)	0.66148 (18)	0.7019 (2)	0.0439 (5)
C5	0.8222 (3)	0.48727 (18)	0.6187 (3)	0.0482 (6)
H5A	0.8906	0.4482	0.6038	0.058*
H5B	0.7453	0.4997	0.5239	0.058*
C3	0.8863 (2)	0.34948 (19)	0.8204 (3)	0.0439 (5)
H3A	0.9638	0.3916	0.8854	0.053*
H3B	0.9165	0.3025	0.7663	0.053*
C9	0.7113 (2)	0.49168 (18)	0.7904 (2)	0.0371 (5)
H9	0.7779	0.5045	0.8922	0.044*
C8	0.6607 (2)	0.59613 (19)	0.7111 (3)	0.0463 (6)
H8A	0.6205	0.6371	0.7613	0.056*
H8B	0.5900	0.5822	0.6130	0.056*
C6	0.8809 (3)	0.59178 (19)	0.6909 (3)	0.0510 (6)
H6A	0.9192	0.6282	0.6350	0.061*
H6B	0.9540	0.5790	0.7881	0.061*
C12	0.7281 (3)	0.8340 (2)	0.6265 (3)	0.0637 (7)
H12A	0.6419	0.8713	0.5805	0.076*
H12B	0.7934	0.8703	0.6032	0.076*
C10	0.5940 (2)	0.4216 (2)	0.7848 (3)	0.0467 (6)
H10A	0.6061	0.4061	0.8825	0.056*
H10B	0.5065	0.4560	0.7300	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0895 (3)	0.04123 (17)	0.0633 (2)	−0.00573 (13)	0.04119 (18)	−0.00022 (12)
O1	0.0431 (9)	0.0423 (8)	0.0294 (8)	−0.0076 (7)	0.0142 (7)	−0.0022 (6)
O2	0.0890 (14)	0.0478 (10)	0.0373 (10)	−0.0019 (10)	0.0129 (10)	0.0008 (8)
O3	0.0545 (10)	0.0443 (9)	0.0425 (9)	0.0021 (8)	0.0068 (8)	−0.0056 (7)
C1	0.0489 (14)	0.0453 (13)	0.0364 (12)	−0.0032 (10)	0.0223 (11)	0.0011 (10)
C11	0.0321 (12)	0.0482 (13)	0.0380 (13)	−0.0066 (10)	0.0134 (10)	0.0023 (10)
C13	0.0602 (17)	0.0420 (14)	0.0590 (17)	−0.0012 (12)	0.0246 (14)	−0.0077 (12)
C4	0.0335 (12)	0.0383 (11)	0.0327 (12)	−0.0032 (9)	0.0153 (10)	−0.0047 (10)
C2	0.0453 (14)	0.0514 (14)	0.0364 (13)	0.0075 (11)	0.0094 (11)	0.0049 (11)
C7	0.0488 (14)	0.0384 (12)	0.0372 (13)	−0.0014 (11)	0.0132 (11)	−0.0032 (10)
C5	0.0584 (16)	0.0430 (13)	0.0569 (15)	−0.0040 (11)	0.0382 (13)	−0.0051 (11)
C3	0.0313 (12)	0.0458 (12)	0.0504 (14)	0.0011 (10)	0.0149 (11)	−0.0047 (11)
C9	0.0325 (12)	0.0443 (12)	0.0337 (12)	0.0026 (9)	0.0144 (10)	−0.0042 (10)
C8	0.0370 (12)	0.0462 (14)	0.0493 (15)	0.0067 (10)	0.0140 (11)	−0.0024 (11)
C6	0.0516 (15)	0.0453 (14)	0.0621 (16)	−0.0098 (11)	0.0311 (13)	−0.0067 (12)
C12	0.075 (2)	0.0490 (16)	0.0596 (17)	0.0066 (14)	0.0237 (15)	0.0063 (13)
C10	0.0399 (13)	0.0549 (14)	0.0508 (14)	0.0033 (11)	0.0255 (12)	0.0035 (12)

Geometric parameters (Å, º) top

Br1—C1	1.979 (2)	C2—H2B	0.9700
O1—C11	1.430 (3)	C7—C6	1.519 (3)
O1—C4	1.449 (3)	C7—C8	1.533 (4)
O2—C12	1.384 (3)	C5—C6	1.511 (3)
O2—C7	1.430 (3)	C5—H5A	0.9700
O3—C13	1.416 (3)	C5—H5B	0.9700
O3—C7	1.424 (3)	C3—H3A	0.9700
C1—C2	1.512 (3)	C3—H3B	0.9700
C1—C11	1.519 (3)	C9—C8	1.520 (3)
C1—H1	0.9800	C9—C10	1.547 (3)
C11—C10	1.528 (3)	C9—H9	0.9800
C11—H11	0.9800	C8—H8A	0.9700
C13—C12	1.498 (4)	C8—H8B	0.9700
C13—H13A	0.9700	C6—H6A	0.9700
C13—H13B	0.9700	C6—H6B	0.9700
C4—C3	1.524 (3)	C12—H12A	0.9700
C4—C5	1.531 (3)	C12—H12B	0.9700
C4—C9	1.552 (3)	C10—H10A	0.9700
C2—C3	1.529 (3)	C10—H10B	0.9700
C2—H2A	0.9700

C11—O1—C4	104.04 (15)	C4—C5—H5A	109.5
C12—O2—C7	109.37 (19)	C6—C5—H5B	109.5
C13—O3—C7	107.58 (18)	C4—C5—H5B	109.5
C2—C1—C11	111.43 (19)	H5A—C5—H5B	108.1
C2—C1—Br1	110.40 (16)	C4—C3—C2	111.99 (18)
C11—C1—Br1	108.80 (15)	C4—C3—H3A	109.2
C2—C1—H1	108.7	C2—C3—H3A	109.2
C11—C1—H1	108.7	C4—C3—H3B	109.2
Br1—C1—H1	108.7	C2—C3—H3B	109.2
O1—C11—C1	110.25 (17)	H3A—C3—H3B	107.9
O1—C11—C10	103.78 (17)	C8—C9—C10	112.51 (19)
C1—C11—C10	110.77 (19)	C8—C9—C4	111.12 (18)
O1—C11—H11	110.6	C10—C9—C4	102.94 (18)
C1—C11—H11	110.6	C8—C9—H9	110.0
C10—C11—H11	110.6	C10—C9—H9	110.0
O3—C13—C12	103.1 (2)	C4—C9—H9	110.0
O3—C13—H13A	111.2	C9—C8—C7	113.1 (2)
C12—C13—H13A	111.2	C9—C8—H8A	108.9
O3—C13—H13B	111.2	C7—C8—H8A	108.9
C12—C13—H13B	111.2	C9—C8—H8B	108.9
H13A—C13—H13B	109.1	C7—C8—H8B	108.9
O1—C4—C3	107.08 (17)	H8A—C8—H8B	107.8
O1—C4—C5	107.98 (17)	C5—C6—C7	111.8 (2)
C3—C4—C5	113.22 (18)	C5—C6—H6A	109.3
O1—C4—C9	103.17 (16)	C7—C6—H6A	109.3
C3—C4—C9	112.15 (18)	C5—C6—H6B	109.3
C5—C4—C9	112.49 (18)	C7—C6—H6B	109.3
C1—C2—C3	111.68 (18)	H6A—C6—H6B	107.9
C1—C2—H2A	109.3	O2—C12—C13	106.1 (2)
C3—C2—H2A	109.3	O2—C12—H12A	110.5
C1—C2—H2B	109.3	C13—C12—H12A	110.5
C3—C2—H2B	109.3	O2—C12—H12B	110.5
H2A—C2—H2B	107.9	C13—C12—H12B	110.5
O3—C7—O2	105.78 (18)	H12A—C12—H12B	108.7
O3—C7—C6	107.5 (2)	C11—C10—C9	104.20 (17)
O2—C7—C6	111.1 (2)	C11—C10—H10A	110.9
O3—C7—C8	112.2 (2)	C9—C10—H10A	110.9
O2—C7—C8	108.2 (2)	C11—C10—H10B	110.9
C6—C7—C8	111.80 (19)	C9—C10—H10B	110.9
C6—C5—C4	110.50 (19)	H10A—C10—H10B	108.9
C6—C5—H5A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.98	2.53	3.445 (3)	156
C1—H1···O1ⁱⁱ	0.98	2.57	3.471 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₉BrO₃
M_r	303.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.0159 (3), 12.6619 (3), 10.2763 (2)
β (°)	117.044 (1)
V (Å³)	1276.63 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.21
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.446, 0.644
No. of measured, independent and observed [I > 2σ(I)] reflections	11338, 2368, 1859
R_int	0.027

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.076, 1.02
No. of reflections	2368
No. of parameters	154
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.32

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.98	2.53	3.445 (3)	156.0
C1—H1···O1ⁱⁱ	0.98	2.57	3.471 (3)	153.3

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

Acknowledgements

TBK thanks the University Grants Commission, India for the award of Dr Kothari post-doctoral fellowship. We thank Mr Saikat Sen for his help in determining the X-ray crystal structure at the CCD facility of the Indian Institute of Science (IISc), Bangalore. GM acknowledges the research support from Eli Lilly and Jubilant-Bhartia Foundations.

References

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Volume 68| Part 8| August 2012| Pages o2411-o2412

https://doi.org/10.1107/S1600536812029777

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

(1′S,6′S,8′S,9′R)-9′-Bromo-12′-oxa­spiro­[1,3-dioxolane-2,4′-tri­cyclo­[6.3.1.01,6]dodeca­ne]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1′S,6′S,8′S,9′R)-9′-Bromo-12′-oxaspiro[1,3-dioxolane-2,4′-tricyclo[6.3.1.0^1,6]dodecane]