[(1S,2S,3R,4R)-3-Hydr­oxy-4,7,7-tri­methyl­bicyclo­[2.2.1]heptan-2-yl]methyl[(E)-3-(trimethyl­silyl)prop-2-enyl]selen­onium bromide

Wang, H.-Y.; Zhang, Q.; Li, Y.-Z.; Gui, Y.; Huang, Z.-Z.

doi:10.1107/S1600536808016863

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1245

doi:10.1107/S1600536808016863

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[(1S,2S,3R,4R)-3-Hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]methyl[(E)-3-(trimethylsilyl)prop-2-enyl]selenonium bromide

Hai-Yang Wang,^a Qiang Zhang,^a Yi-Zhi Li,^b Yuan Gui ^a and Zhi-Zhen Huang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China, and ^bState Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China
^*Correspondence e-mail: llyyjz@nju.edu.cn

(Received 23 May 2008; accepted 3 June 2008; online 7 June 2008)

The title compound, a selenonium bromide, C₁₇H₃₃OSeSi⁺·Br⁻, was obtained from the reaction of enantiomerically pure 4,7,7-trimethyl-2-methylselanylbicyclo[2.2.1]heptan-3-ol and (3-bromopropenyl)trimethylsilane in acetone. Due to the chiral bicyclic substituent, the crystal structure is not centrosymmetric and has no symmetry plane, with four chiral C atoms in the cation. The asymmetric unit contains one selenonium cation and one bromide anion. C–H⋯Br and O–H⋯Br hydrogen bonds link the ions, forming a one-dimensional R-helical chain-like supramolecular structure.

Related literature

For related literature, see: Li et al. (2005 ); Goodridge et al. (1988 ); Reich et al. (1975 ); Ye et al. (2002 ).

Experimental

Crystal data

C₁₇H₃₃OSeSi⁺·Br⁻
M_r = 440.39
Monoclinic, P 2₁
a = 7.555 (2) Å
b = 10.023 (2) Å
c = 14.423 (3) Å
β = 101.29 (3)°
V = 1071.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 3.67 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.35, T_max = 0.41
4460 measured reflections
3374 independent reflections
1732 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.102
S = 1.07
3374 reflections
170 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.74 e Å⁻³
Absolute structure: Flack (1983 ), 1140 Friedel pairs
Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯Br1	0.87 (8)	2.28 (8)	3.143 (5)	175 (7)
C5—H5⋯Br1ⁱ	0.98	2.88	3.827 (5)	164
C11—H11C⋯Br1ⁱⁱ	0.96	2.94	3.874 (7)	165
C12—H12B⋯Br1ⁱ	0.97	2.97	3.855 (5)	152
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) x, y-1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016863/im2070sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016863/im2070Isup2.hkl

checkCIF report

Comment top

Recently, an efficient asymmetric synthesis of cyclopropanes via camphor-derived sulfonium ylides was reported (Ye et al., 2002). Thus, we expected that camphor-derived selenonium ylides could be used in the highly enantioselective synthesis of cyclopropanes, epoxides and aziridines. First, the camphor-derived selenide (1) was prepared from commercially available D-camphor according to a literature method (Reich et al., 1975; Goodridge et al., 1988, and Li et al., 2005). Then compound (1) was reacted with (3-bromo-propenyl)-trimethylsilane (3) to give the selenonium salt (2). We performed the X-ray crystallographic analysis of (2) in order to elucidate the conformation and configuration.

The structural analysis shows that the selenonium ion of the title compound, (2) (Fig. 1), is not centrosymmetric and has no symmetry plane, showing the four chiral C atoms, C4, C5, C6, and C7, with the R, R, S, and S configuration preserved from the enatiomerically pure starting compound (1). The asymmetric unit contains one selenonium salt cation, and one bromide ion. In the crystal packing, the Br atom plays an important role, acting as a bridge linking neighboring molecules via C–H···Br and O–H···Br hydrogen bonds (O1—H1D···Br1, C5—H5···Br1ⁱⁱ, C11—H11c···Br1ⁱ, and C12—H12B···Br1ⁱⁱ; symmetry code i: x,-1 + y,z; ii: 1 - x,-1/2 + y, -z), forming a one dimensional R-helical chains-like structure along [010] axis (Fig. 2).

Related literature top

For related literature, see: Li et al. (2005); Goodridge et al. (1988); Reich et al. (1975); Ye et al. (2002)

Experimental top

A solution of 4,7,7-trimethyl-2-methylselanyl-bicyclo[2.2.1]heptan-3-ol (1) (2.4 g, 9.7 mmol) and (3-bromo-propenyl)-trimethylsilane (3) (1.9 g, 9.7 mmol) in acetone (5 mL) was stirred at 273 K. The solid was collected and washed with ethyl ether to afford the selenonium salt (2) in 91% yield. Single crystals of (2) were obtained by slow evaporation from 10 mL of a methanolic solution containing 50 mg (2).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : View of the title compound, showing the labelling of the non-H atoms and 30% probability ellipsoids. H atoms have been omitted for clarity, except for H1D which is involved in hydrogen bonding.
	Fig. 2. : A view of the onedimensional R-helical chains along the [010] axis. H atoms have been omitted for clarity, except for H1D, H5, H11c, and H12B which are involved in hydrogen bonding.
	Fig. 3. : Reaction scheme.

[(1S,2S,3R,4R)-3-Hydroxy-4,7,7- trimethylbicyclo[2.2.1]hept-2-yl]methyl[(E)-3-(trimethylsilyl)prop-2- enyl]selenonium bromide top

Crystal data top

C₁₇H₃₃OSeSi⁺·Br⁻	F(000) = 452
M_r = 440.39	D_x = 1.366 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 895 reflections
a = 7.555 (2) Å	θ = 2.1–24.5°
b = 10.023 (2) Å	µ = 3.67 mm⁻¹
c = 14.423 (3) Å	T = 291 K
β = 101.29 (3)°	Bloc, colourless
V = 1071.0 (4) Å³	0.30 × 0.26 × 0.24 mm
Z = 2

Data collection top

Bruker SMART Apex CCD diffractometer	3374 independent reflections
Radiation source: sealed tube	1732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
phi and ω scans	θ_max = 26.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.35, T_max = 0.41	k = 0→12
4460 measured reflections	l = 0→17

Refinement top

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.046P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3374 reflections	Δρ_max = 0.64 e Å⁻³
170 parameters	Δρ_min = −0.74 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1140 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

C₁₇H₃₃OSeSi⁺·Br⁻	V = 1071.0 (4) Å³
M_r = 440.39	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.555 (2) Å	µ = 3.67 mm⁻¹
b = 10.023 (2) Å	T = 291 K
c = 14.423 (3) Å	0.30 × 0.26 × 0.24 mm
β = 101.29 (3)°

Data collection top

Bruker SMART Apex CCD diffractometer	3374 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1732 reflections with I > 2σ(I)
T_min = 0.35, T_max = 0.41	R_int = 0.035
4460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	Δρ_max = 0.64 e Å⁻³
S = 1.07	Δρ_min = −0.74 e Å⁻³
3374 reflections	Absolute structure: Flack (1983), 1140 Friedel pairs
170 parameters	Absolute structure parameter: 0.01 (2)
1 restraint

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	0.32321 (7)	1.05851 (10)	0.09364 (5)	0.0584 (2)
C1	0.6248 (8)	0.4347 (6)	0.3285 (4)	0.0404 (14)
H1A	0.6335	0.3442	0.3079	0.061*
H1B	0.5363	0.4400	0.3679	0.061*
H1C	0.7399	0.4630	0.3637	0.061*
C2	0.7389 (6)	0.5504 (10)	0.2095 (4)	0.0425 (13)
H2A	0.8154	0.6083	0.2529	0.064*
H2B	0.7085	0.5928	0.1488	0.064*
H2C	0.8013	0.4683	0.2036	0.064*
C3	0.5706 (8)	0.5219 (6)	0.2454 (5)	0.0498 (18)
C4	0.4232 (11)	0.4559 (8)	0.1682 (5)	0.0445 (19)
H4	0.4615	0.3724	0.1428	0.053*
C5	0.3867 (6)	0.5695 (8)	0.0960 (4)	0.0361 (12)
H5	0.4822	0.5710	0.0588	0.043*
C6	0.3996 (9)	0.6917 (8)	0.1552 (5)	0.0398 (16)
H6	0.4963	0.7496	0.1422	0.048*
C7	0.4459 (9)	0.6398 (7)	0.2553 (4)	0.0473 (15)
C8	0.2804 (6)	0.5707 (9)	0.2761 (4)	0.0406 (14)
H8A	0.1744	0.6264	0.2578	0.049*
H8B	0.2955	0.5499	0.3428	0.049*
C9	0.2627 (8)	0.4411 (7)	0.2161 (5)	0.0460 (15)
H9A	0.2728	0.3619	0.2555	0.055*
H9B	0.1499	0.4384	0.1704	0.055*
C10	0.5215 (9)	0.7500 (7)	0.3273 (5)	0.047
H10A	0.6407	0.7741	0.3196	0.071*
H10B	0.5262	0.7175	0.3903	0.071*
H10C	0.4444	0.8269	0.3166	0.071*
C11	0.2014 (9)	0.3828 (7)	−0.0510 (5)	0.043
H11A	0.3020	0.3955	−0.0816	0.064*
H11B	0.0971	0.3576	−0.0970	0.064*
H11C	0.2294	0.3137	−0.0043	0.064*
C12	0.2030 (8)	0.6908 (7)	−0.0809 (4)	0.0415 (15)
H12A	0.1683	0.7780	−0.0614	0.050*
H12B	0.3310	0.6926	−0.0820	0.050*
C13	0.0925 (8)	0.6561 (7)	−0.1810 (4)	0.0430 (15)
H13	−0.0322	0.6663	−0.1918	0.052*
C14	0.1643 (8)	0.6141 (6)	−0.2502 (4)	0.0385 (13)
H14	0.2893	0.6068	−0.2395	0.046*
C15	−0.0572 (9)	0.3993 (7)	−0.3683 (5)	0.047
H15A	−0.1696	0.4027	−0.3468	0.071*
H15B	0.0262	0.3436	−0.3267	0.071*
H15C	−0.0771	0.3631	−0.4311	0.071*
C16	−0.1393 (8)	0.6949 (7)	−0.4057 (5)	0.041
H16A	−0.2022	0.6764	−0.4689	0.061*
H16B	−0.0837	0.7813	−0.4039	0.061*
H16C	−0.2231	0.6937	−0.3636	0.061*
C17	0.1943 (7)	0.5796 (7)	−0.4543 (4)	0.049
H17A	0.2631	0.4987	−0.4522	0.073*
H17B	0.2746	0.6536	−0.4372	0.073*
H17C	0.1259	0.5926	−0.5171	0.073*
O1	0.2297 (6)	0.7626 (5)	0.1376 (3)	0.0473 (11)
H1D	0.248 (10)	0.845 (8)	0.125 (5)	0.057*
Se1	0.15165 (6)	0.54982 (7)	0.01059 (4)	0.04094 (15)
Si1	0.03564 (18)	0.5673 (2)	−0.36882 (11)	0.0395 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0503 (3)	0.0494 (4)	0.0775 (5)	−0.0034 (4)	0.0172 (3)	−0.0074 (5)
C1	0.043 (3)	0.043 (4)	0.040 (3)	0.000 (3)	0.020 (3)	0.000 (3)
C2	0.031 (2)	0.049 (3)	0.043 (3)	−0.012 (4)	−0.0060 (19)	−0.021 (5)
C3	0.038 (3)	0.046 (4)	0.053 (4)	−0.019 (3)	−0.020 (3)	0.003 (3)
C4	0.059 (4)	0.038 (4)	0.034 (4)	−0.005 (3)	0.004 (3)	0.008 (3)
C5	0.035 (2)	0.037 (3)	0.035 (3)	0.019 (3)	0.0062 (18)	0.005 (3)
C6	0.034 (3)	0.048 (4)	0.040 (4)	−0.005 (3)	0.013 (3)	0.003 (3)
C7	0.052 (3)	0.047 (3)	0.037 (4)	0.001 (3)	−0.003 (3)	0.006 (3)
C8	0.042 (2)	0.049 (4)	0.035 (3)	0.016 (3)	0.017 (2)	−0.009 (3)
C9	0.034 (3)	0.046 (4)	0.055 (4)	−0.004 (3)	0.004 (3)	0.005 (3)
C10	0.049	0.049	0.049	0.000	0.021	0.000
C11	0.044	0.044	0.044	0.000	0.018	0.000
C12	0.039 (3)	0.051 (4)	0.036 (3)	0.020 (3)	0.012 (3)	0.009 (3)
C13	0.045 (3)	0.048 (4)	0.033 (3)	0.005 (3)	0.002 (3)	0.014 (3)
C14	0.044 (3)	0.044 (3)	0.029 (3)	−0.004 (2)	0.012 (2)	−0.002 (3)
C15	0.049	0.049	0.049	0.000	0.021	0.000
C16	0.043	0.043	0.043	0.000	0.020	0.000
C17	0.050	0.050	0.050	0.000	0.020	0.000
O1	0.046 (2)	0.049 (3)	0.038 (2)	−0.010 (2)	−0.0126 (19)	0.003 (2)
Se1	0.0358 (2)	0.0516 (3)	0.0339 (3)	0.0028 (4)	0.00292 (19)	0.0086 (4)
Si1	0.0420 (7)	0.0402 (9)	0.0380 (8)	0.0077 (9)	0.0119 (6)	−0.0030 (10)

Geometric parameters (Å, º) top

Br1—O1	3.143 (5)	C10—H10B	0.9600
C1—C3	1.475 (9)	C10—H10C	0.9600
C1—H1A	0.9600	C11—Se1	1.965 (7)
C1—H1B	0.9600	C11—H11A	0.9600
C1—H1C	0.9600	C11—H11B	0.9600
C2—C3	1.492 (8)	C11—H11C	0.9600
C2—H2A	0.9600	C12—C13	1.560 (9)
C2—H2B	0.9600	C12—Se1	2.022 (6)
C2—H2C	0.9600	C12—H12A	0.9700
C3—C7	1.535 (9)	C12—H12B	0.9700
C3—C4	1.559 (9)	C13—C14	1.295 (8)
C4—C9	1.515 (10)	C13—H13	0.9300
C4—C5	1.531 (10)	C14—Si1	1.855 (6)
C4—H4	0.9800	C14—H14	0.9300
C5—C6	1.484 (10)	C15—Si1	1.825 (7)
C5—Se1	1.963 (5)	C15—H15A	0.9600
C5—H5	0.9800	C15—H15B	0.9600
C6—O1	1.446 (8)	C15—H15C	0.9600
C6—C7	1.510 (9)	C16—Si1	1.842 (7)
C6—H6	0.9800	C16—H16A	0.9600
C7—C8	1.510 (9)	C16—H16B	0.9600
C7—C10	1.546 (9)	C16—H16C	0.9600
C8—C9	1.552 (10)	C17—Si1	1.884 (5)
C8—H8A	0.9700	C17—H17A	0.9600
C8—H8B	0.9700	C17—H17B	0.9600
C9—H9A	0.9700	C17—H17C	0.9600
C9—H9B	0.9700	O1—H1D	0.87 (8)
C10—H10A	0.9600

C3—C1—H1A	109.5	C7—C10—H10A	109.5
C3—C1—H1B	109.5	C7—C10—H10B	109.5
H1A—C1—H1B	109.5	H10A—C10—H10B	109.5
C3—C1—H1C	109.5	C7—C10—H10C	109.5
H1A—C1—H1C	109.5	H10A—C10—H10C	109.5
H1B—C1—H1C	109.5	H10B—C10—H10C	109.5
C3—C2—H2A	109.5	Se1—C11—H11A	109.5
C3—C2—H2B	109.5	Se1—C11—H11B	109.5
H2A—C2—H2B	109.5	H11A—C11—H11B	109.5
C3—C2—H2C	109.5	Se1—C11—H11C	109.5
H2A—C2—H2C	109.5	H11A—C11—H11C	109.5
H2B—C2—H2C	109.5	H11B—C11—H11C	109.5
C1—C3—C2	106.0 (5)	C13—C12—Se1	108.2 (4)
C1—C3—C7	117.3 (6)	C13—C12—H12A	110.1
C2—C3—C7	117.8 (6)	Se1—C12—H12A	110.1
C1—C3—C4	112.0 (5)	C13—C12—H12B	110.1
C2—C3—C4	111.8 (6)	Se1—C12—H12B	110.1
C7—C3—C4	91.6 (5)	H12A—C12—H12B	108.4
C9—C4—C5	109.2 (6)	C14—C13—C12	123.8 (5)
C9—C4—C3	103.9 (6)	C14—C13—H13	118.1
C5—C4—C3	100.3 (5)	C12—C13—H13	118.1
C9—C4—H4	114.0	C13—C14—Si1	124.7 (5)
C5—C4—H4	114.0	C13—C14—H14	117.6
C3—C4—H4	114.0	Si1—C14—H14	117.6
C6—C5—C4	103.8 (5)	Si1—C15—H15A	109.5
C6—C5—Se1	113.2 (4)	Si1—C15—H15B	109.5
C4—C5—Se1	111.9 (5)	H15A—C15—H15B	109.5
C6—C5—H5	109.3	Si1—C15—H15C	109.5
C4—C5—H5	109.3	H15A—C15—H15C	109.5
Se1—C5—H5	109.3	H15B—C15—H15C	109.5
O1—C6—C5	110.4 (5)	Si1—C16—H16A	109.5
O1—C6—C7	111.6 (5)	Si1—C16—H16B	109.5
C5—C6—C7	104.1 (6)	H16A—C16—H16B	109.5
O1—C6—H6	110.2	Si1—C16—H16C	109.5
C5—C6—H6	110.2	H16A—C16—H16C	109.5
C7—C6—H6	110.2	H16B—C16—H16C	109.5
C6—C7—C8	107.5 (5)	Si1—C17—H17A	109.5
C6—C7—C3	102.0 (5)	Si1—C17—H17B	109.5
C8—C7—C3	102.2 (5)	H17A—C17—H17B	109.5
C6—C7—C10	112.5 (6)	Si1—C17—H17C	109.5
C8—C7—C10	114.0 (6)	H17A—C17—H17C	109.5
C3—C7—C10	117.4 (5)	H17B—C17—H17C	109.5
C7—C8—C9	105.0 (5)	C6—O1—Br1	105.8 (4)
C7—C8—H8A	110.8	C6—O1—H1D	109 (5)
C9—C8—H8A	110.8	C5—Se1—C11	98.0 (3)
C7—C8—H8B	110.8	C5—Se1—C12	94.2 (3)
C9—C8—H8B	110.8	C11—Se1—C12	102.9 (3)
H8A—C8—H8B	108.8	C15—Si1—C16	112.8 (3)
C4—C9—C8	100.5 (5)	C15—Si1—C14	111.2 (3)
C4—C9—H9A	111.7	C16—Si1—C14	107.9 (3)
C8—C9—H9A	111.7	C15—Si1—C17	110.9 (3)
C4—C9—H9B	111.7	C16—Si1—C17	106.1 (3)
C8—C9—H9B	111.7	C14—Si1—C17	107.6 (3)
H9A—C9—H9B	109.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Br1	0.87 (8)	2.28 (8)	3.143 (5)	175 (7)
C5—H5···Br1ⁱ	0.98	2.88	3.827 (5)	164
C11—H11C···Br1ⁱⁱ	0.96	2.94	3.874 (7)	165
C12—H12B···Br1ⁱ	0.97	2.97	3.855 (5)	152

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

Experimental details

Crystal data
Chemical formula	C₁₇H₃₃OSeSi⁺·Br⁻
M_r	440.39
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	7.555 (2), 10.023 (2), 14.423 (3)
β (°)	101.29 (3)
V (Å³)	1071.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.67
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART Apex CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.35, 0.41
No. of measured, independent and observed [I > 2σ(I)] reflections	4460, 3374, 1732
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.102, 1.07
No. of reflections	3374
No. of parameters	170
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)	0.64, −0.74
Absolute structure	Flack (1983), 1140 Friedel pairs
Absolute structure parameter	0.01 (2)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Br1	0.87 (8)	2.28 (8)	3.143 (5)	175 (7)
C5—H5···Br1ⁱ	0.98	2.88	3.827 (5)	163.5
C11—H11C···Br1ⁱⁱ	0.96	2.94	3.874 (7)	164.5
C12—H12B···Br1ⁱ	0.97	2.97	3.855 (5)	152.0

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

Acknowledgements

We thank the National Natural Science Foundation of China for its financial support of projects 20332050 and 20572042

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goodridge, R. J., Hambley, T. W., Hayes, R. K. & Ridley, D. D. (1988). J. Org. Chem. 53, 2881–2889. CSD CrossRef CAS Google Scholar
Li, X. L., Wang, Y. & Huang, Z. Z. (2005). Aust. J. Chem. 58, 749–752. Web of Science CrossRef CAS Google Scholar
Reich, H. J., Renga, J. M. & Reich, I. J. (1975). J. Am. Chem. Soc. 97, 5434–5447. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ye, S., Huang, Z. Z., Xia, C. A., Tang, Y. & Dai, L. X. (2002). J. Am. Chem. Soc. 124, 2432–2433. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 64| Part 7| July 2008| Page o1245

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

[(1S,2S,3R,4R)-3-Hydr­­oxy-4,7,7-tri­methyl­bi­cyclo­[2.2.1]heptan-2-yl]methyl[(E)-3-(tri­methyl­silyl)prop-2-enyl]selen­onium bromide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[(1S,2S,3R,4R)-3-Hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]methyl[(E)-3-(trimethylsilyl)prop-2-enyl]selenonium bromide