6-Meth­oxy-2-phenyl-4,4a,6,7,8,8a-hexa­hydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diyl bis­(4-methyl­benzene-1-sulfonate)

Wardell, J.L.; Tiekink, E.R.T.

doi:10.1107/S1600536812006186

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o758

doi:10.1107/S1600536812006186

Open

access

6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diyl bis(4-methylbenzene-1-sulfonate)

James L. Wardell ^a ‡ and Edward R. T. Tiekink ^b ^*

^aCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Avenida Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 February 2012; accepted 12 February 2012; online 17 February 2012)

In the title α-D-glucopyranoside derivative, C₂₈H₃₀O₁₀S₂, each heterocyclic ring adopts a chair conformation. In the trisubstituted ring, the methoxy and one sulfonate group occupy axial positions, whereas the second sulfonate group occupies an axial position. The phenyl group on the other ring is in an equatorial position. In the crystal, supramolecular chains propagating along [100] are formed through C—H⋯O and C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Brown et al. (1995 ); Whistler (1962 ). For the ¹³C NMR spectrum, see: Sugiyama et al. (1978 ).

Experimental

Crystal data

C₂₈H₃₀O₁₀S₂
M_r = 590.64
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.7031 (16) Å
b = 17.020 (5) Å
c = 28.084 (8) Å
V = 2726.0 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.20 × 0.01 × 0.01 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ) T_min = 0.747, T_max = 1.000
25991 measured reflections
6262 independent reflections
5326 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.147
S = 1.18
6262 reflections
364 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ), with 2656 Friedel pairs
Flack parameter: 0.21 (11)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C23–C28 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O7ⁱ	1.00	2.59	3.548 (5)	162
C8—H8B⋯O1ⁱ	0.98	2.50	3.325 (6)	142
C10—H10⋯O7ⁱ	0.95	2.47	3.023 (6)	117
C20—H20⋯Cg1ⁱ	0.95	2.79	3.479 (5)	130
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006186/hb6633sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006186/hb6633Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006186/hb6633Isup3.cml

checkCIF report

Comment top

The title compound was prepared initially as a precursor for a series of 2-metallated derivatives of methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranosides (Brown et al., 1995).

In (I), Fig. 1, both heterocyclic rings adopt a chair conformation. With respect to the fused heterocyclic rings, the phenyl and S2-sulfonate groups are approximately co-planar but, the S1-sulfonate group lies to one side, and the methoxy group to the other. In the O1-ring, the O4 and O5 substituents occupy axial positions whereas the O5 substituent is equatorial. In the O2-ring, the phenyl group is in an equatorial position.

In the crystal, C—H···O and C—H···π interactions link translationally related molecules into a supramolecular chain along [100], Fig. 2 and Table 1. Chains pack with no specific intermolecular interactions between them, Fig. 3.

Related literature top

For the synthesis of the title compound, see: Brown et al. (1995); Whistler (1962). For the ¹³C NMR spectrum, see: Sugiyama et al. (1978).

Experimental top

The title compound was obtained from methyl 4,6-O-benzylidene-α-D-glucopyranoside and p-toluenesulfonyl chloride using a published procedure (Brown et al., 1995; Whistler, 1962), m.p. 426–428 K. The ¹³C NMR spectrum was identical with that published (Sugiyama et al., 1978).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the linear supramolecular chain along [100] in (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively. H atoms not involved in the supramolecular interactions have been omitted for clarity.
	Fig. 3. A view in projection down the a axis of the packing of supramolecular chains in (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively. One supramolecular chain has been highlighted in space-filling mode.

6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydro-2H- pyrano[3,2-d][1,3]dioxine-7,8-diyl bis(4-methylbenzene-1-sulfonate) top

Crystal data top

C₂₈H₃₀O₁₀S₂	F(000) = 1240
M_r = 590.64	D_x = 1.439 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9688 reflections
a = 5.7031 (16) Å	θ = 2.4–31.4°
b = 17.020 (5) Å	µ = 0.25 mm⁻¹
c = 28.084 (8) Å	T = 100 K
V = 2726.0 (14) Å³	Needle, colourless
Z = 4	0.20 × 0.01 × 0.01 mm

Data collection top

Rigaku Saturn724+ diffractometer	6262 independent reflections
Radiation source: Rotating Anode	5326 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.103
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
profile data from ω–scans	h = −7→5
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −22→22
T_min = 0.747, T_max = 1.000	l = −36→36
25991 measured reflections

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)] = 0.082	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0335P)² + 1.481P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max < 0.001
6262 reflections	Δρ_max = 0.30 e Å⁻³
364 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 2656 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.21 (11)

Crystal data top

C₂₈H₃₀O₁₀S₂	V = 2726.0 (14) Å³
M_r = 590.64	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.7031 (16) Å	µ = 0.25 mm⁻¹
b = 17.020 (5) Å	T = 100 K
c = 28.084 (8) Å	0.20 × 0.01 × 0.01 mm

Data collection top

Rigaku Saturn724+ diffractometer	6262 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	5326 reflections with I > 2σ(I)
T_min = 0.747, T_max = 1.000	R_int = 0.103
25991 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.147	Δρ_max = 0.30 e Å⁻³
S = 1.18	Δρ_min = −0.38 e Å⁻³
6262 reflections	Absolute structure: Flack (1983), with 2656 Friedel pairs
364 parameters	Absolute structure parameter: 0.21 (11)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.5416 (2)	−0.05008 (7)	0.71777 (4)	0.0194 (3)
S2	0.0901 (2)	0.09753 (6)	0.59013 (4)	0.0214 (3)
O1	0.4150 (6)	−0.20508 (16)	0.61006 (9)	0.0164 (7)
O2	0.4498 (5)	−0.05358 (16)	0.51713 (9)	0.0162 (6)
O3	0.5946 (6)	−0.17301 (16)	0.48707 (10)	0.0186 (7)
O4	0.0148 (5)	−0.18698 (16)	0.62785 (10)	0.0158 (7)
O5	0.5053 (5)	−0.06571 (16)	0.66275 (10)	0.0168 (7)
O6	0.4090 (6)	−0.10660 (18)	0.74447 (10)	0.0245 (8)
O7	0.7922 (5)	−0.04735 (18)	0.72221 (11)	0.0232 (7)
O8	0.3017 (6)	0.03820 (16)	0.59950 (10)	0.0187 (7)
O9	−0.1278 (6)	0.05763 (18)	0.59845 (12)	0.0277 (8)
O10	0.1498 (7)	0.16567 (17)	0.61702 (12)	0.0306 (9)
C1	0.2469 (8)	−0.1719 (2)	0.64186 (15)	0.0156 (9)
H1	0.2724	−0.1942	0.6744	0.019*
C2	0.2700 (8)	−0.0829 (2)	0.64421 (15)	0.0154 (9)
H2	0.1466	−0.0600	0.6653	0.019*
C3	0.2614 (8)	−0.0455 (2)	0.59468 (15)	0.0161 (9)
H3	0.1050	−0.0551	0.5797	0.019*
C4	0.4517 (8)	−0.0828 (2)	0.56520 (14)	0.0149 (9)
H4	0.6079	−0.0725	0.5801	0.018*
C5	0.6340 (8)	−0.0903 (2)	0.49103 (15)	0.0167 (9)
H5	0.7864	−0.0810	0.5077	0.020*
C6	0.5940 (9)	−0.2098 (2)	0.53331 (14)	0.0190 (10)
H6A	0.7491	−0.2034	0.5486	0.023*
H6B	0.5617	−0.2667	0.5300	0.023*
C7	0.4060 (8)	−0.1715 (2)	0.56347 (14)	0.0150 (9)
H7	0.2486	−0.1816	0.5490	0.018*
C8	−0.0436 (9)	−0.2694 (2)	0.63036 (16)	0.0232 (11)
H8A	0.0214	−0.2967	0.6026	0.035*
H8B	−0.2144	−0.2756	0.6307	0.035*
H8C	0.0226	−0.2920	0.6595	0.035*
C9	0.4247 (8)	0.0431 (3)	0.72699 (14)	0.0184 (9)
C10	0.2123 (9)	0.0499 (3)	0.75107 (16)	0.0222 (10)
H10	0.1389	0.0047	0.7643	0.027*
C11	0.1086 (10)	0.1235 (3)	0.75561 (17)	0.0270 (11)
H11	−0.0389	0.1282	0.7711	0.032*
C12	0.2174 (9)	0.1902 (3)	0.73783 (16)	0.0240 (11)
C13	0.4373 (9)	0.1825 (3)	0.71563 (17)	0.0266 (11)
H13	0.5174	0.2281	0.7049	0.032*
C14	0.5373 (9)	0.1099 (2)	0.70937 (15)	0.0217 (10)
H14	0.6827	0.1052	0.6931	0.026*
C15	0.1022 (11)	0.2697 (3)	0.74185 (19)	0.0381 (14)
H15A	−0.0680	0.2638	0.7385	0.057*
H15B	0.1614	0.3042	0.7166	0.057*
H15C	0.1383	0.2926	0.7730	0.057*
C16	0.1142 (9)	0.1205 (2)	0.52932 (15)	0.0184 (10)
C17	0.3093 (9)	0.1617 (2)	0.51311 (17)	0.0212 (10)
H17	0.4347	0.1732	0.5342	0.025*
C18	0.3201 (9)	0.1857 (2)	0.46615 (17)	0.0227 (11)
H18	0.4541	0.2133	0.4550	0.027*
C19	0.1355 (10)	0.1698 (2)	0.43491 (16)	0.0246 (11)
C20	−0.0548 (9)	0.1276 (3)	0.45155 (17)	0.0267 (11)
H20	−0.1796	0.1157	0.4303	0.032*
C21	−0.0680 (9)	0.1023 (2)	0.49803 (16)	0.0221 (10)
H21	−0.1995	0.0729	0.5087	0.027*
C22	0.1410 (11)	0.2005 (3)	0.38427 (18)	0.0373 (14)
H22A	0.0745	0.1610	0.3628	0.056*
H22B	0.3034	0.2114	0.3750	0.056*
H22C	0.0485	0.2489	0.3822	0.056*
C23	0.6480 (8)	−0.0578 (2)	0.44167 (14)	0.0161 (9)
C24	0.4715 (8)	−0.0126 (2)	0.42182 (15)	0.0199 (10)
H24	0.3351	−0.0008	0.4399	0.024*
C25	0.4936 (9)	0.0159 (3)	0.37499 (16)	0.0244 (11)
H25	0.3720	0.0469	0.3615	0.029*
C26	0.6925 (9)	−0.0012 (3)	0.34847 (17)	0.0269 (12)
H26	0.7071	0.0181	0.3169	0.032*
C27	0.8701 (9)	−0.0465 (3)	0.36821 (16)	0.0238 (10)
H27	1.0055	−0.0589	0.3500	0.029*
C28	0.8494 (8)	−0.0738 (2)	0.41477 (15)	0.0188 (10)
H28	0.9731	−0.1036	0.4284	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0230 (7)	0.0209 (5)	0.0143 (5)	−0.0029 (5)	−0.0011 (5)	−0.0003 (4)
S2	0.0258 (7)	0.0170 (5)	0.0214 (6)	0.0064 (5)	0.0024 (5)	−0.0009 (4)
O1	0.0212 (18)	0.0168 (14)	0.0112 (14)	0.0029 (14)	0.0029 (14)	0.0018 (11)
O2	0.0199 (17)	0.0173 (14)	0.0115 (13)	0.0039 (13)	0.0027 (13)	0.0018 (12)
O3	0.0251 (19)	0.0163 (14)	0.0146 (14)	0.0010 (14)	0.0036 (14)	−0.0011 (12)
O4	0.0112 (17)	0.0146 (14)	0.0216 (15)	−0.0015 (12)	−0.0001 (13)	−0.0007 (12)
O5	0.0167 (18)	0.0201 (15)	0.0136 (14)	−0.0015 (13)	−0.0009 (13)	−0.0051 (12)
O6	0.031 (2)	0.0244 (16)	0.0183 (16)	−0.0072 (16)	0.0004 (16)	0.0053 (13)
O7	0.0188 (18)	0.0279 (17)	0.0228 (17)	−0.0025 (15)	−0.0030 (15)	−0.0024 (15)
O8	0.0248 (18)	0.0114 (13)	0.0200 (16)	0.0011 (13)	0.0006 (14)	−0.0017 (12)
O9	0.0199 (19)	0.0273 (17)	0.036 (2)	0.0041 (15)	0.0104 (16)	0.0071 (15)
O10	0.045 (2)	0.0181 (16)	0.0287 (18)	0.0070 (16)	−0.0013 (18)	−0.0059 (14)
C1	0.014 (2)	0.020 (2)	0.013 (2)	−0.0005 (18)	0.0020 (18)	−0.0021 (17)
C2	0.013 (2)	0.019 (2)	0.014 (2)	−0.0028 (18)	0.0025 (18)	−0.0013 (17)
C3	0.022 (3)	0.0128 (19)	0.014 (2)	−0.0015 (18)	−0.0005 (19)	−0.0025 (17)
C4	0.018 (2)	0.0164 (19)	0.0107 (19)	0.0029 (18)	0.0004 (18)	0.0026 (15)
C5	0.016 (3)	0.0163 (19)	0.018 (2)	0.0004 (18)	0.0011 (19)	0.0013 (17)
C6	0.027 (3)	0.0151 (19)	0.015 (2)	0.001 (2)	0.001 (2)	0.0022 (17)
C7	0.015 (2)	0.0171 (19)	0.0131 (19)	0.0035 (18)	−0.0048 (19)	−0.0006 (16)
C8	0.029 (3)	0.017 (2)	0.024 (2)	−0.003 (2)	−0.001 (2)	0.0026 (18)
C9	0.022 (3)	0.023 (2)	0.0101 (19)	−0.003 (2)	−0.0036 (19)	−0.0075 (17)
C10	0.025 (3)	0.021 (2)	0.021 (2)	−0.008 (2)	0.001 (2)	−0.0062 (19)
C11	0.021 (3)	0.033 (3)	0.027 (3)	−0.006 (2)	0.005 (2)	−0.013 (2)
C12	0.030 (3)	0.025 (2)	0.018 (2)	−0.002 (2)	−0.002 (2)	−0.011 (2)
C13	0.032 (3)	0.023 (2)	0.025 (2)	−0.007 (2)	0.000 (3)	0.002 (2)
C14	0.029 (3)	0.023 (2)	0.014 (2)	−0.004 (2)	0.008 (2)	−0.0013 (17)
C15	0.043 (4)	0.027 (3)	0.043 (3)	0.000 (3)	0.008 (3)	−0.006 (2)
C16	0.020 (3)	0.0128 (19)	0.022 (2)	0.0045 (18)	−0.001 (2)	0.0017 (17)
C17	0.020 (3)	0.014 (2)	0.030 (3)	−0.0032 (19)	−0.007 (2)	−0.0016 (19)
C18	0.026 (3)	0.013 (2)	0.029 (3)	−0.004 (2)	−0.001 (2)	0.0024 (18)
C19	0.033 (3)	0.018 (2)	0.023 (2)	0.007 (2)	−0.001 (2)	0.0048 (19)
C20	0.025 (3)	0.026 (2)	0.029 (3)	0.001 (2)	−0.011 (2)	0.002 (2)
C21	0.025 (3)	0.0129 (19)	0.028 (2)	−0.004 (2)	0.000 (2)	−0.0001 (18)
C22	0.051 (4)	0.029 (3)	0.032 (3)	0.016 (3)	−0.005 (3)	0.005 (2)
C23	0.020 (3)	0.0150 (19)	0.014 (2)	0.0004 (18)	0.0030 (19)	0.0003 (17)
C24	0.018 (3)	0.023 (2)	0.018 (2)	−0.0002 (19)	0.004 (2)	0.0030 (17)
C25	0.028 (3)	0.027 (2)	0.018 (2)	−0.004 (2)	−0.005 (2)	0.0035 (19)
C26	0.032 (3)	0.030 (2)	0.019 (2)	−0.014 (2)	−0.004 (2)	0.004 (2)
C27	0.021 (3)	0.034 (3)	0.017 (2)	−0.002 (2)	0.004 (2)	−0.002 (2)
C28	0.019 (3)	0.021 (2)	0.016 (2)	−0.0050 (19)	0.001 (2)	0.0023 (17)

Geometric parameters (Å, º) top

S1—O7	1.435 (3)	C10—C11	1.392 (6)
S1—O6	1.435 (3)	C10—H10	0.9500
S1—O5	1.581 (3)	C11—C12	1.386 (7)
S1—C9	1.740 (4)	C11—H11	0.9500
S2—O10	1.425 (3)	C12—C13	1.406 (7)
S2—O9	1.435 (3)	C12—C15	1.508 (6)
S2—O8	1.595 (3)	C13—C14	1.372 (6)
S2—C16	1.757 (4)	C13—H13	0.9500
O1—C1	1.427 (5)	C14—H14	0.9500
O1—C7	1.429 (4)	C15—H15A	0.9800
O2—C5	1.426 (5)	C15—H15B	0.9800
O2—C4	1.439 (4)	C15—H15C	0.9800
O3—C5	1.429 (5)	C16—C17	1.392 (6)
O3—C6	1.442 (5)	C16—C21	1.396 (6)
O4—C1	1.404 (5)	C17—C18	1.382 (6)
O4—C8	1.444 (5)	C17—H17	0.9500
O5—C2	1.469 (5)	C18—C19	1.397 (7)
O8—C3	1.449 (4)	C18—H18	0.9500
C1—C2	1.522 (5)	C19—C20	1.383 (7)
C1—H1	1.0000	C19—C22	1.515 (6)
C2—C3	1.531 (6)	C20—C21	1.377 (6)
C2—H2	1.0000	C20—H20	0.9500
C3—C4	1.505 (6)	C21—H21	0.9500
C3—H3	1.0000	C22—H22A	0.9800
C4—C7	1.532 (5)	C22—H22B	0.9800
C4—H4	1.0000	C22—H22C	0.9800
C5—C23	1.495 (5)	C23—C24	1.384 (6)
C5—H5	1.0000	C23—C28	1.402 (6)
C6—C7	1.514 (6)	C24—C25	1.407 (6)
C6—H6A	0.9900	C24—H24	0.9500
C6—H6B	0.9900	C25—C26	1.388 (7)
C7—H7	1.0000	C25—H25	0.9500
C8—H8A	0.9800	C26—C27	1.389 (7)
C8—H8B	0.9800	C26—H26	0.9500
C8—H8C	0.9800	C27—C28	1.393 (6)
C9—C10	1.392 (6)	C27—H27	0.9500
C9—C14	1.397 (6)	C28—H28	0.9500

O7—S1—O6	120.1 (2)	C10—C9—C14	120.3 (4)
O7—S1—O5	102.74 (18)	C10—C9—S1	118.8 (4)
O6—S1—O5	109.21 (18)	C14—C9—S1	120.9 (4)
O7—S1—C9	109.8 (2)	C9—C10—C11	119.3 (4)
O6—S1—C9	109.3 (2)	C9—C10—H10	120.4
O5—S1—C9	104.40 (18)	C11—C10—H10	120.4
O10—S2—O9	120.4 (2)	C12—C11—C10	120.9 (5)
O10—S2—O8	104.30 (19)	C12—C11—H11	119.5
O9—S2—O8	109.19 (17)	C10—C11—H11	119.5
O10—S2—C16	108.4 (2)	C11—C12—C13	118.9 (5)
O9—S2—C16	109.3 (2)	C11—C12—C15	120.8 (5)
O8—S2—C16	103.98 (19)	C13—C12—C15	120.3 (5)
C1—O1—C7	113.0 (3)	C14—C13—C12	120.7 (4)
C5—O2—C4	109.0 (3)	C14—C13—H13	119.6
C5—O3—C6	111.0 (3)	C12—C13—H13	119.6
C1—O4—C8	112.4 (3)	C13—C14—C9	119.8 (4)
C2—O5—S1	120.0 (3)	C13—C14—H14	120.1
C3—O8—S2	119.1 (3)	C9—C14—H14	120.1
O4—C1—O1	112.7 (3)	C12—C15—H15A	109.5
O4—C1—C2	106.0 (3)	C12—C15—H15B	109.5
O1—C1—C2	111.3 (3)	H15A—C15—H15B	109.5
O4—C1—H1	108.9	C12—C15—H15C	109.5
O1—C1—H1	108.9	H15A—C15—H15C	109.5
C2—C1—H1	108.9	H15B—C15—H15C	109.5
O5—C2—C1	107.0 (3)	C17—C16—C21	120.1 (4)
O5—C2—C3	105.6 (3)	C17—C16—S2	119.5 (4)
C1—C2—C3	111.9 (3)	C21—C16—S2	120.3 (4)
O5—C2—H2	110.7	C18—C17—C16	119.8 (5)
C1—C2—H2	110.7	C18—C17—H17	120.1
C3—C2—H2	110.7	C16—C17—H17	120.1
O8—C3—C4	110.6 (3)	C17—C18—C19	120.5 (5)
O8—C3—C2	108.6 (3)	C17—C18—H18	119.7
C4—C3—C2	107.5 (3)	C19—C18—H18	119.7
O8—C3—H3	110.0	C20—C19—C18	118.7 (4)
C4—C3—H3	110.0	C20—C19—C22	120.8 (5)
C2—C3—H3	110.0	C18—C19—C22	120.5 (5)
O2—C4—C3	111.4 (3)	C21—C20—C19	121.7 (5)
O2—C4—C7	108.0 (3)	C21—C20—H20	119.1
C3—C4—C7	108.1 (4)	C19—C20—H20	119.1
O2—C4—H4	109.8	C20—C21—C16	119.1 (4)
C3—C4—H4	109.8	C20—C21—H21	120.4
C7—C4—H4	109.8	C16—C21—H21	120.4
O2—C5—O3	110.9 (3)	C19—C22—H22A	109.5
O2—C5—C23	110.7 (3)	C19—C22—H22B	109.5
O3—C5—C23	107.5 (3)	H22A—C22—H22B	109.5
O2—C5—H5	109.2	C19—C22—H22C	109.5
O3—C5—H5	109.2	H22A—C22—H22C	109.5
C23—C5—H5	109.2	H22B—C22—H22C	109.5
O3—C6—C7	108.6 (3)	C24—C23—C28	119.2 (4)
O3—C6—H6A	110.0	C24—C23—C5	122.7 (4)
C7—C6—H6A	110.0	C28—C23—C5	118.1 (4)
O3—C6—H6B	110.0	C23—C24—C25	120.2 (4)
C7—C6—H6B	110.0	C23—C24—H24	119.9
H6A—C6—H6B	108.4	C25—C24—H24	119.9
O1—C7—C6	108.3 (3)	C26—C25—C24	120.1 (5)
O1—C7—C4	111.0 (3)	C26—C25—H25	119.9
C6—C7—C4	108.8 (4)	C24—C25—H25	119.9
O1—C7—H7	109.6	C25—C26—C27	119.9 (4)
C6—C7—H7	109.6	C25—C26—H26	120.1
C4—C7—H7	109.6	C27—C26—H26	120.1
O4—C8—H8A	109.5	C26—C27—C28	119.9 (5)
O4—C8—H8B	109.5	C26—C27—H27	120.1
H8A—C8—H8B	109.5	C28—C27—H27	120.1
O4—C8—H8C	109.5	C27—C28—C23	120.7 (4)
H8A—C8—H8C	109.5	C27—C28—H28	119.7
H8B—C8—H8C	109.5	C23—C28—H28	119.7

O7—S1—O5—C2	171.9 (3)	O5—S1—C9—C10	107.5 (3)
O6—S1—O5—C2	43.4 (3)	O7—S1—C9—C14	39.0 (4)
C9—S1—O5—C2	−73.4 (3)	O6—S1—C9—C14	172.7 (4)
O10—S2—O8—C3	155.0 (3)	O5—S1—C9—C14	−70.6 (4)
O9—S2—O8—C3	25.1 (3)	C14—C9—C10—C11	2.7 (7)
C16—S2—O8—C3	−91.5 (3)	S1—C9—C10—C11	−175.3 (4)
C8—O4—C1—O1	66.1 (4)	C9—C10—C11—C12	−2.0 (7)
C8—O4—C1—C2	−172.0 (3)	C10—C11—C12—C13	−1.0 (7)
C7—O1—C1—O4	64.3 (4)	C10—C11—C12—C15	178.7 (5)
C7—O1—C1—C2	−54.6 (5)	C11—C12—C13—C14	3.4 (7)
S1—O5—C2—C1	−95.2 (3)	C15—C12—C13—C14	−176.2 (5)
S1—O5—C2—C3	145.5 (3)	C12—C13—C14—C9	−2.7 (7)
O4—C1—C2—O5	175.3 (3)	C10—C9—C14—C13	−0.4 (7)
O1—C1—C2—O5	−61.9 (4)	S1—C9—C14—C13	177.7 (4)
O4—C1—C2—C3	−69.6 (4)	O10—S2—C16—C17	45.1 (4)
O1—C1—C2—C3	53.2 (5)	O9—S2—C16—C17	178.1 (3)
S2—O8—C3—C4	132.3 (3)	O8—S2—C16—C17	−65.4 (4)
S2—O8—C3—C2	−109.9 (3)	O10—S2—C16—C21	−130.6 (4)
O5—C2—C3—O8	−59.8 (4)	O9—S2—C16—C21	2.4 (4)
C1—C2—C3—O8	−175.8 (3)	O8—S2—C16—C21	118.9 (3)
O5—C2—C3—C4	59.9 (4)	C21—C16—C17—C18	1.2 (6)
C1—C2—C3—C4	−56.1 (5)	S2—C16—C17—C18	−174.5 (3)
C5—O2—C4—C3	179.6 (3)	C16—C17—C18—C19	0.7 (7)
C5—O2—C4—C7	−61.9 (4)	C17—C18—C19—C20	−1.8 (7)
O8—C3—C4—O2	−64.2 (4)	C17—C18—C19—C22	176.3 (4)
C2—C3—C4—O2	177.4 (3)	C18—C19—C20—C21	1.1 (7)
O8—C3—C4—C7	177.3 (3)	C22—C19—C20—C21	−176.9 (4)
C2—C3—C4—C7	58.8 (4)	C19—C20—C21—C16	0.7 (7)
C4—O2—C5—O3	64.4 (4)	C17—C16—C21—C20	−1.8 (6)
C4—O2—C5—C23	−176.4 (3)	S2—C16—C21—C20	173.8 (3)
C6—O3—C5—O2	−62.6 (5)	O2—C5—C23—C24	−13.9 (6)
C6—O3—C5—C23	176.3 (4)	O3—C5—C23—C24	107.3 (4)
C5—O3—C6—C7	57.9 (5)	O2—C5—C23—C28	165.9 (4)
C1—O1—C7—C6	178.9 (3)	O3—C5—C23—C28	−72.9 (5)
C1—O1—C7—C4	59.6 (5)	C28—C23—C24—C25	0.8 (6)
O3—C6—C7—O1	−176.8 (3)	C5—C23—C24—C25	−179.4 (4)
O3—C6—C7—C4	−56.0 (4)	C23—C24—C25—C26	0.0 (7)
O2—C4—C7—O1	177.6 (3)	C24—C25—C26—C27	0.0 (7)
C3—C4—C7—O1	−61.7 (5)	C25—C26—C27—C28	−0.8 (7)
O2—C4—C7—C6	58.5 (4)	C26—C27—C28—C23	1.7 (7)
C3—C4—C7—C6	179.2 (3)	C24—C23—C28—C27	−1.6 (6)
O7—S1—C9—C10	−143.0 (3)	C5—C23—C28—C27	178.6 (4)
O6—S1—C9—C10	−9.3 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C23–C28 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O7ⁱ	1.00	2.59	3.548 (5)	162
C8—H8B···O1ⁱ	0.98	2.50	3.325 (6)	142
C10—H10···O7ⁱ	0.95	2.47	3.023 (6)	117
C20—H20···Cg1ⁱ	0.95	2.79	3.479 (5)	130

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₈H₃₀O₁₀S₂
M_r	590.64
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.7031 (16), 17.020 (5), 28.084 (8)
V (Å³)	2726.0 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.20 × 0.01 × 0.01

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2011)
T_min, T_max	0.747, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	25991, 6262, 5326
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.147, 1.18
No. of reflections	6262
No. of parameters	364
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.38
Absolute structure	Flack (1983), with 2656 Friedel pairs
Absolute structure parameter	0.21 (11)

Computer programs: CrystalClear-SM Expert (Rigaku, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C23–C28 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O7ⁱ	1.00	2.59	3.548 (5)	162
C8—H8B···O1ⁱ	0.98	2.50	3.325 (6)	142
C10—H10···O7ⁱ	0.95	2.47	3.023 (6)	117
C20—H20···Cg1ⁱ	0.95	2.79	3.479 (5)	130

Symmetry code: (i) x−1, y, z.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there are gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Brown, M. A., Cox, P. J., Howie, R. A., Melvin, O. A., Taylor, O. J. & Wardell, J. L. (1995). J. Organomet. Chem. 498, 275–282. CSD CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sugiyama, H., Yamasaki, T., Senda, Y., Ishiyama, J., Matsuda, K. & Seto, S. (1978). Bull. Chem. Soc. Jpn, 51, 3659–3660. CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Whistler, R. (1962). Methods in Carbohydrate Chemistry, Vol. 1, pp. 308–351. New York: Academic Press. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o758

doi:10.1107/S1600536812006186

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

6-Meth­­oxy-2-phenyl-4,4a,6,7,8,8a-hexa­hydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diyl bis­­(4-methyl­benzene-1-sulfonate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diyl bis(4-methylbenzene-1-sulfonate)