1,2,3,4,5,6-Hexa-O-acetyl-scyllo-inositol

Kant, R.; Gupta, V.K.; Kapoor, K.; Chib, R.; Shah, B.A.; Taneja, S.C.

doi:10.1107/S1600536812033600

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2594

https://doi.org/10.1107/S1600536812033600

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1,2,3,4,5,6-Hexa-O-acetyl-scyllo-inositol

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Renu Chib,^b Bhahwal A. Shah ^b and Subhash C. Taneja ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bNatural Product Microbes Division, Indian, Institute of Integrative Medicine, Canal Road, Jammu Tawi 180 001, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 6 July 2012; accepted 25 July 2012; online 28 July 2012)

The title molecule, C₁₈H₂₄O₁₂, has crystallographic 2/m symmetry with two acetate group located on a mirror plane. The H—Csp³—O—Csp² torsion angles characterizing orientation of the acetyl groups with respect to the cyclohexane ring are 0.0, 23.9 and −23.9°. The cyclohexane ring is in a chair conformation with all substituents in equatorial positions. In the crystal, molecules are connected through C—H⋯O hydrogen bonds into a chain extending along the c axis.

Related literature

For applications of the title compound, see: Kamal & Mathur (1991 ); Anonymous et al. (2001 , 2003 ). For related structures, see: Abboud et al. (1990 ).

Experimental

Crystal data

C₁₈H₂₄O₁₂
M_r = 432.37
Monoclinic, C 2/m
a = 12.901 (3) Å
b = 14.013 (3) Å
c = 5.8572 (12) Å
β = 97.33 (2)°
V = 1050.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.472, T_max = 1.000
3652 measured reflections
959 independent reflections
626 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.198
S = 1.08
959 reflections
77 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4ⁱ	0.98	2.57	3.393 (4)	141
Symmetry code: (i) x, -y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812033600/gk2511sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812033600/gk2511Isup2.hkl

checkCIF report

Comment top

Parthenium hysterophorus (Asteraceae) is an annual weed. It is commonly known as congress weed, carrot weed, star weed, feverfew etc. A decoction of the root of P. hysterophorus finds use in treatment of dysentery (Anonymous et al., 2001). Histamine (0.35%) is present in the roots of plant (Kamal & Mathur, 1991). The roots contain parthenin, caffeic, chlorogenic, p-hydroxybenzoic, p-anisic, vanilic, salicylic, gentisic, neo-chlorogenic and proto-catechuic acids (Anonymous et al., 2003). Roots of this plant were not that much explored thus making this an interesting field to carry out further studies.

In the title compound (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related structure (Abboud et al., 1990). The twist angles characterizing orientation of the acetyl group with respect to the cyclohexane ring are: H1—C1—O2—C3 = -23.9°, H2—C2—O1—C5 = 0.0°. The cyclohexyl ring is in the chair conformation. Intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains along the c axis..

Related literature top

For applications of the title compound, see: Kamal & Mathur (1991); Anonymous et al. (2001, 2003). For related structures, see: Abboud et al. (1990).

Experimental top

Dried roots (2 kg) of P. hysterophorus was crushed, water extract was prepared and lyophilized. Dry powder (5 g) obtained was treated with pyridine (50 ml) and acetic anhydride (60 ml) and was stirred at room temperature. Progress of the reaction was checked by TLC. After completion of the reaction, mixture was treated dropwise with 1.5 N aqueous HCl (50 ml) and then extracted with ethyl acetate (3x100mL). After usual workup and removal of the solvents the reaction product obtained was 8 g. Chromatographic separation of the products on a silica gel column using chloroform: methanol (99:1 to 80:20) as eluent, gave pure myo-inositol hexaacetate and later fractions gave scyllo-inositol hexaacetate as white crystals m.p. 651–653 K. Single crystal of the compound was grown by slow evaporation technique using methanol /chloroform as the solvent system.

Structure description top

For applications of the title compound, see: Kamal & Mathur (1991); Anonymous et al. (2001, 2003). For related structures, see: Abboud et al. (1990).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Symmetry operations generating the whole molecule from the asymmetric part are: 1-x, -y, 1-z and x, -y, z.
	Fig. 2. The packing arrangement of molecules viewed down the a axis. For clarity, hydrogen atoms which are not involved in hydrogen bonding have been omitted.

1,2,3,4,5,6-Hexa-O-acetyl-scyllo-inositol top

Crystal data top

C₁₈H₂₄O₁₂	F(000) = 456
M_r = 432.37	D_x = 1.367 Mg m⁻³
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 1553 reflections
a = 12.901 (3) Å	θ = 3.5–29.1°
b = 14.013 (3) Å	µ = 0.12 mm⁻¹
c = 5.8572 (12) Å	T = 293 K
β = 97.33 (2)°	Block, white
V = 1050.2 (4) Å³	0.3 × 0.2 × 0.2 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	959 independent reflections
Radiation source: fine-focus sealed tube	626 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
Detector resolution: 16.1049 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scan	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −16→16
T_min = 0.472, T_max = 1.000	l = −6→6
3652 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.198	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1032P)²P] where P = (F_o² + 2F_c²)/3
959 reflections	(Δ/σ)_max = 0.001
77 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₂₄O₁₂	V = 1050.2 (4) Å³
M_r = 432.37	Z = 2
Monoclinic, C2/m	Mo Kα radiation
a = 12.901 (3) Å	µ = 0.12 mm⁻¹
b = 14.013 (3) Å	T = 293 K
c = 5.8572 (12) Å	0.3 × 0.2 × 0.2 mm
β = 97.33 (2)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	959 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	626 reflections with I > 2σ(I)
T_min = 0.472, T_max = 1.000	R_int = 0.081
3652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.198	H-atom parameters constrained
S = 1.08	Δρ_max = 0.37 e Å⁻³
959 reflections	Δρ_min = −0.30 e Å⁻³
77 parameters

Special details top

Experimental. Absorption correction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
O1	0.3027 (2)	0.0000	0.6341 (4)	0.0412 (8)
O2	0.42280 (15)	0.16670 (15)	0.6695 (3)	0.0448 (7)
O3	0.3640 (2)	0.26466 (17)	0.3790 (4)	0.0660 (8)
O4	0.3169 (3)	0.0000	1.0179 (5)	0.0722 (12)
C1	0.4426 (2)	0.0905 (2)	0.5150 (4)	0.0373 (8)
H1	0.3991	0.0978	0.3662	0.045*
C2	0.4142 (3)	0.0000	0.6355 (6)	0.0376 (10)
H2	0.4485	0.0000	0.7947	0.045*
C3	0.3838 (2)	0.2500 (2)	0.5799 (6)	0.0483 (9)
C4	0.3714 (3)	0.3192 (3)	0.7664 (6)	0.0695 (12)
H4A	0.4360	0.3526	0.8080	0.104*
H4B	0.3527	0.2857	0.8981	0.104*
H4C	0.3174	0.3641	0.7136	0.104*
C5	0.2635 (4)	0.0000	0.8365 (8)	0.0450 (11)
C6	0.1486 (4)	0.0000	0.7967 (8)	0.0566 (13)
H6A	0.1257	0.0000	0.6342	0.085*
H6B	0.1226	0.0559	0.8650	0.085*	0.50
H6C	0.1226	−0.0559	0.8650	0.085*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0386 (16)	0.0466 (18)	0.0389 (16)	0.000	0.0071 (12)	0.000
O2	0.0514 (14)	0.0377 (13)	0.0449 (12)	0.0038 (10)	0.0042 (10)	−0.0055 (9)
O3	0.0836 (19)	0.0463 (15)	0.0667 (17)	0.0192 (14)	0.0036 (13)	0.0052 (12)
O4	0.078 (3)	0.095 (3)	0.045 (2)	0.000	0.0124 (17)	0.000
C1	0.0416 (17)	0.0317 (16)	0.0377 (16)	0.0024 (14)	0.0020 (13)	−0.0030 (12)
C2	0.040 (2)	0.034 (2)	0.038 (2)	0.000	0.0020 (16)	0.000
C3	0.0431 (18)	0.0376 (19)	0.063 (2)	0.0026 (15)	0.0026 (15)	−0.0027 (15)
C4	0.071 (2)	0.050 (2)	0.086 (3)	0.006 (2)	0.001 (2)	−0.0216 (19)
C5	0.057 (3)	0.031 (2)	0.049 (3)	0.000	0.016 (2)	0.000
C6	0.056 (3)	0.044 (3)	0.076 (3)	0.000	0.029 (2)	0.000

Geometric parameters (Å, º) top

O1—C5	1.347 (5)	C2—H2	0.9800
O1—C2	1.438 (5)	C3—C4	1.485 (4)
O2—C3	1.350 (4)	C4—H4A	0.9600
O2—C1	1.443 (3)	C4—H4B	0.9600
O3—C3	1.189 (4)	C4—H4C	0.9600
O4—C5	1.190 (5)	C5—C6	1.471 (6)
C1—C1ⁱ	1.514 (5)	C6—H6A	0.9600
C1—C2	1.519 (3)	C6—H6B	0.9600
C1—H1	0.9800	C6—H6C	0.9600
C2—C1ⁱⁱ	1.519 (3)

C5—O1—C2	118.8 (3)	O2—C3—C4	110.4 (3)
C3—O2—C1	118.8 (2)	C3—C4—H4A	109.5
O2—C1—C1ⁱ	109.09 (19)	C3—C4—H4B	109.5
O2—C1—C2	104.7 (2)	H4A—C4—H4B	109.5
C1ⁱ—C1—C2	110.6 (2)	C3—C4—H4C	109.5
O2—C1—H1	110.8	H4A—C4—H4C	109.5
C1ⁱ—C1—H1	110.8	H4B—C4—H4C	109.5
C2—C1—H1	110.8	O4—C5—O1	123.1 (4)
O1—C2—C1ⁱⁱ	107.3 (2)	O4—C5—C6	126.7 (4)
O1—C2—C1	107.3 (2)	O1—C5—C6	110.1 (4)
C1ⁱⁱ—C2—C1	113.3 (3)	C5—C6—H6A	109.5
O1—C2—H2	109.6	C5—C6—H6B	109.5
C1ⁱⁱ—C2—H2	109.6	H6A—C6—H6B	109.5
C1—C2—H2	109.6	C5—C6—H6C	109.5
O3—C3—O2	123.8 (3)	H6A—C6—H6C	109.5
O3—C3—C4	125.8 (3)	H6B—C6—H6C	109.5

C3—O2—C1—C1ⁱ	98.2 (3)	O2—C1—C2—C1ⁱⁱ	−172.6 (2)
C3—O2—C1—C2	−143.4 (3)	C1ⁱ—C1—C2—C1ⁱⁱ	−55.2 (4)
C5—O1—C2—C1ⁱⁱ	119.0 (2)	C1—O2—C3—O3	0.4 (5)
C5—O1—C2—C1	−119.0 (2)	C1—O2—C3—C4	−178.8 (2)
O2—C1—C2—O1	69.1 (3)	C2—O1—C5—O4	0.0
C1ⁱ—C1—C2—O1	−173.5 (2)	C2—O1—C5—C6	180.0

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱⁱⁱ	0.98	2.57	3.393 (4)	141

Symmetry code: (iii) x, −y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₄O₁₂
M_r	432.37
Crystal system, space group	Monoclinic, C2/m
Temperature (K)	293
a, b, c (Å)	12.901 (3), 14.013 (3), 5.8572 (12)
β (°)	97.33 (2)
V (Å³)	1050.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.472, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3652, 959, 626
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.198, 1.08
No. of reflections	959
No. of parameters	77
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.30

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱ	0.98	2.57	3.393 (4)	141

Symmetry code: (i) x, −y, z−1.

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

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Anonymous (2001). The Wealth of India (Raw Materials Series), Vol. VII p. 268. New Delhi: NISCOM. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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