3,4-O-Isopropyl­idene-2,7-di-O-p-tolyl­sulfonyl-α-l-xylo-3-heptulo-3,6-furan­osononitrile

Ma, L.; Li, Y.-F.; Meng, X.-B.; Li, Z.-J.

doi:10.1107/S1600536809032565

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2437

doi:10.1107/S1600536809032565

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3,4-O-Isopropylidene-2,7-di-O-p-tolylsulfonyl-α-L-xylo-3-heptulo-3,6-furanosononitrile

Liang Ma,^a Yun-Feng Li,^a ^* Xiang-Bao Meng ^a and Zhong-Jun Li ^b

^aDepartment of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, People's Republic of China, and ^bState Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, People's Republic of China
^*Correspondence e-mail: zjli@bjmu.edu.cn

(Received 7 April 2009; accepted 17 August 2009; online 12 September 2009)

In the title compound, C₂₄H₂₇NO₁₀S₂, derived from L-sorbofuranose, the fused five-membered rings display envelope conformations. The two tosylate branches are in equatorial positions with respect to the furanose ring, while the hydroxy group is in the axial position. In the crystal structure, the hydroxy group is involved in intermolecular O—H⋯O hydrogen bonds, linking molecules in chains along [100].

Related literature

For details of the synthesis, see: Bianchi et al. (2001 ); Georges & Fraser-Reid (1984 ); Sharma et al. (2003 ); Szarek et al. (1997 ).

Experimental

Crystal data

C₂₄H₂₇NO₁₀S₂
M_r = 553.59
Monoclinic, P 2₁
a = 5.6342 (11) Å
b = 28.771 (6) Å
c = 8.3226 (17) Å
β = 103.00 (3)°
V = 1314.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 113 K
0.16 × 0.12 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.960, T_max = 0.980
8980 measured reflections
4781 independent reflections
4228 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.127
S = 1.05
4781 reflections
339 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.51 e Å⁻³
Absolute structure: Flack (1983 ), 1570 Friedel pairs
Flack parameter: 0.07 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4ⁱ	0.82	2.03	2.844 (3)	169
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: 10.1107/S1600536809032565/bh2226sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032565/bh2226Isup2.hkl

checkCIF report

Comment top

The skeleton of the title compound is a derivative of L-sorbofuranose and consists of two tosyl, a cyano and a bridged ring. Both five-membered rings display an envelope conformation. The hydroxy group lies in axial bond of the furanose ring. The two tosylate branches lie in equatorial bonds of the five-membered furanose ring. The synthesis has been adapted from published procedures (Bianchi et al., 2001; Georges & Fraser-Reid, 1984; Sharma et al., 2003; Szarek et al., 1997).

Related literature top

For details of the synthesis, see: Bianchi et al. (2001); Georges & Fraser-Reid (1984); Sharma et al. (2003); Szarek et al. (1997).

Experimental top

The title compound was synthesized from the original compound 2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose and the procedures are as follows: 2,3:4,6-di-O-isopropylidene-α-L-xylo-hexos-2-ulofuranose (obtained from the oxidization of 2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose) was dissolved in HOAc (80%), followed by addition of NaCN, and after stirred at room temperature for 24 h., 3,4:5,7-di-O-isopropylidene-α-L-xylo-3-heptulo-3,6-furanosononititrile was formed. The reaction mixture was then directly heated at 323 K for 12 h. to remove 4,6-isopropylidene, yielding 3,4-O-isopropylidene-α-L-xylo-3-heptulo-3,6-furanosononititrile as a white solid after concentration in vacuo and subsequent column chromatography (petroleum-ethyl acetate 1:1). Finally 3,4-O-isopropylidene-α-L-xylo-3-heptulo-3,6-furanosononititrile was dissolved in pyridine followed by addition of tosyl chloride, and the reaction mixture was stirred at room temperature for 12 h., to obtain the title compound (55% yield over four steps), which was crystallized from petroleum-ethyl acetate (4:1). After a week at room temperature colourless block-like crystals were obtained.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. A view of the title molecule, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size.

3,4-O-Isopropylidene-2,7-di-O-p-tolylsulfonyl- α-L-xylo-3-heptulo-3,6-furanosononitrile top

Crystal data top

C₂₄H₂₇NO₁₀S₂	F(000) = 580
M_r = 553.59	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3787 reflections
a = 5.6342 (11) Å	θ = 1.5–27.5°
b = 28.771 (6) Å	µ = 0.26 mm⁻¹
c = 8.3226 (17) Å	T = 113 K
β = 103.00 (3)°	Block, colourless
V = 1314.5 (5) Å³	0.16 × 0.12 × 0.08 mm
Z = 2

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4781 independent reflections
Radiation source: rotating anode	4228 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.5°
ω and ϕ scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −37→36
T_min = 0.960, T_max = 0.980	l = −8→10
8980 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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0656P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4781 reflections	Δρ_max = 0.31 e Å⁻³
339 parameters	Δρ_min = −0.51 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1570 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (7)

Crystal data top

C₂₄H₂₇NO₁₀S₂	V = 1314.5 (5) Å³
M_r = 553.59	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.6342 (11) Å	µ = 0.26 mm⁻¹
b = 28.771 (6) Å	T = 113 K
c = 8.3226 (17) Å	0.16 × 0.12 × 0.08 mm
β = 103.00 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4781 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	4228 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.980	R_int = 0.039
8980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.127	Δρ_max = 0.31 e Å⁻³
S = 1.05	Δρ_min = −0.51 e Å⁻³
4781 reflections	Absolute structure: Flack (1983), 1570 Friedel pairs
339 parameters	Absolute structure parameter: 0.07 (7)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	−0.32882 (13)	0.19945 (2)	0.07345 (11)	0.01793 (18)
S2	−0.17570 (13)	0.48019 (2)	0.32977 (11)	0.01893 (18)
N1	0.2652 (6)	0.26412 (11)	0.3805 (5)	0.0315 (7)
O1	−0.4314 (4)	0.48295 (9)	0.3207 (3)	0.0262 (6)
O2	−0.0775 (4)	0.49967 (8)	0.2009 (3)	0.0252 (6)
O3	−0.1224 (4)	0.42629 (8)	0.3418 (3)	0.0210 (5)
O4	−0.0948 (4)	0.34836 (7)	0.1318 (3)	0.0196 (5)
O5	0.4380 (4)	0.35399 (8)	0.2068 (3)	0.0244 (5)
H5	0.5668	0.3487	0.1801	0.037*
O6	0.0421 (4)	0.35979 (9)	−0.2024 (3)	0.0267 (6)
O7	−0.2485 (4)	0.31572 (8)	−0.1269 (3)	0.0206 (5)
O8	−0.2598 (4)	0.25334 (7)	0.1007 (3)	0.0196 (5)
O9	−0.2258 (4)	0.18218 (8)	−0.0567 (3)	0.0232 (5)
O10	−0.5865 (4)	0.19956 (9)	0.0566 (3)	0.0232 (5)
C1	−0.0181 (6)	0.50230 (11)	0.5188 (5)	0.0199 (7)
C2	−0.1140 (7)	0.49476 (12)	0.6580 (5)	0.0283 (9)
H2	−0.2577	0.4781	0.6489	0.034*
C3	0.0070 (7)	0.51242 (13)	0.8098 (5)	0.0313 (9)
H3	−0.0570	0.5076	0.9021	0.038*
C4	0.2236 (7)	0.53735 (12)	0.8252 (6)	0.0300 (9)
C5	0.3154 (6)	0.54421 (13)	0.6857 (6)	0.0309 (9)
H5A	0.4591	0.5609	0.6944	0.037*
C6	0.1973 (6)	0.52669 (12)	0.5336 (5)	0.0245 (8)
H6	0.2627	0.5313	0.4417	0.029*
C7	0.3506 (8)	0.55689 (15)	0.9890 (6)	0.0409 (11)
H7A	0.5230	0.5576	0.9960	0.061*
H7B	0.3171	0.5377	1.0757	0.061*
H7C	0.2932	0.5879	1.0000	0.061*
C8	0.1045 (5)	0.40951 (11)	0.3035 (5)	0.0219 (8)
H8A	0.1761	0.3855	0.3814	0.026*
H8B	0.2201	0.4349	0.3119	0.026*
C9	0.0493 (5)	0.39035 (10)	0.1331 (5)	0.0188 (7)
H9	−0.0421	0.4132	0.0560	0.023*
C10	0.2720 (5)	0.37409 (11)	0.0732 (5)	0.0201 (7)
H10	0.3464	0.3996	0.0237	0.024*
C11	0.1613 (5)	0.33768 (11)	−0.0543 (4)	0.0203 (7)
H11	0.2793	0.3142	−0.0711	0.024*
C12	−0.1785 (6)	0.33503 (13)	−0.2688 (5)	0.0234 (7)
C13	−0.0521 (5)	0.31694 (10)	0.0094 (5)	0.0176 (7)
C14	−0.3723 (7)	0.36825 (15)	−0.3504 (5)	0.0363 (10)
H14A	−0.3906	0.3922	−0.2737	0.054*
H14B	−0.5236	0.3519	−0.3856	0.054*
H14C	−0.3271	0.3820	−0.4443	0.054*
C15	−0.1348 (8)	0.29602 (17)	−0.3803 (6)	0.0454 (12)
H15A	−0.0884	0.3088	−0.4753	0.068*
H15B	−0.2813	0.2782	−0.4149	0.068*
H15C	−0.0068	0.2763	−0.3216	0.068*
C16	−0.0202 (5)	0.26825 (11)	0.0850 (4)	0.0177 (7)
H16	0.0402	0.2471	0.0109	0.021*
C17	0.1446 (6)	0.26673 (11)	0.2511 (5)	0.0227 (7)
C18	−0.1844 (5)	0.17379 (10)	0.2592 (4)	0.0159 (6)
C19	0.0301 (6)	0.14921 (11)	0.2676 (5)	0.0222 (7)
H19	0.0925	0.1446	0.1745	0.027*
C20	0.1489 (6)	0.13163 (11)	0.4215 (5)	0.0252 (8)
H20	0.2918	0.1147	0.4297	0.030*
C21	0.0598 (6)	0.13870 (11)	0.5629 (5)	0.0240 (8)
C22	−0.1557 (6)	0.16375 (12)	0.5487 (5)	0.0258 (8)
H22	−0.2179	0.1687	0.6418	0.031*
C23	−0.2790 (6)	0.18142 (11)	0.3976 (5)	0.0212 (7)
H23	−0.4226	0.1981	0.3891	0.025*
C24	0.1933 (8)	0.12001 (14)	0.7275 (5)	0.0345 (10)
H24A	0.3418	0.1054	0.7159	0.052*
H24B	0.0928	0.0976	0.7662	0.052*
H24C	0.2304	0.1451	0.8052	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0172 (3)	0.0193 (3)	0.0174 (5)	−0.0009 (3)	0.0043 (3)	−0.0008 (3)
S2	0.0184 (4)	0.0219 (4)	0.0171 (5)	−0.0002 (3)	0.0051 (3)	−0.0031 (3)
N1	0.0297 (15)	0.0327 (16)	0.030 (2)	0.0054 (13)	0.0026 (15)	0.0022 (15)
O1	0.0184 (10)	0.0325 (13)	0.0280 (16)	0.0019 (10)	0.0060 (11)	−0.0039 (12)
O2	0.0333 (13)	0.0257 (11)	0.0195 (15)	0.0003 (10)	0.0122 (12)	0.0025 (11)
O3	0.0190 (10)	0.0209 (11)	0.0250 (15)	−0.0015 (9)	0.0092 (10)	−0.0048 (10)
O4	0.0154 (10)	0.0175 (10)	0.0292 (15)	−0.0021 (8)	0.0120 (10)	−0.0044 (10)
O5	0.0133 (10)	0.0336 (13)	0.0263 (15)	0.0013 (9)	0.0044 (10)	−0.0012 (11)
O6	0.0279 (12)	0.0332 (12)	0.0208 (15)	−0.0061 (10)	0.0095 (12)	0.0024 (11)
O7	0.0162 (10)	0.0277 (12)	0.0160 (14)	−0.0020 (9)	−0.0004 (10)	0.0049 (10)
O8	0.0144 (9)	0.0201 (10)	0.0253 (15)	0.0019 (9)	0.0063 (10)	0.0009 (10)
O9	0.0295 (12)	0.0239 (11)	0.0186 (14)	−0.0007 (10)	0.0107 (11)	−0.0050 (10)
O10	0.0142 (9)	0.0299 (11)	0.0238 (15)	−0.0014 (9)	0.0009 (10)	0.0019 (12)
C1	0.0204 (14)	0.0194 (14)	0.021 (2)	0.0003 (12)	0.0069 (15)	−0.0031 (14)
C2	0.0321 (18)	0.0293 (17)	0.025 (2)	−0.0092 (14)	0.0108 (18)	0.0008 (16)
C3	0.041 (2)	0.0345 (19)	0.020 (2)	−0.0061 (16)	0.0082 (18)	0.0003 (16)
C4	0.036 (2)	0.0228 (16)	0.031 (3)	0.0041 (14)	0.0057 (18)	−0.0008 (16)
C5	0.0225 (17)	0.0346 (19)	0.035 (3)	−0.0055 (15)	0.0051 (17)	−0.0051 (18)
C6	0.0235 (16)	0.0269 (16)	0.026 (2)	−0.0009 (13)	0.0120 (16)	−0.0033 (15)
C7	0.050 (2)	0.036 (2)	0.032 (3)	0.0001 (18)	−0.001 (2)	−0.005 (2)
C8	0.0146 (13)	0.0243 (16)	0.028 (2)	0.0017 (12)	0.0065 (14)	−0.0043 (15)
C9	0.0149 (13)	0.0161 (13)	0.026 (2)	−0.0016 (11)	0.0054 (14)	−0.0006 (13)
C10	0.0150 (13)	0.0256 (15)	0.020 (2)	−0.0014 (12)	0.0055 (14)	−0.0026 (14)
C11	0.0156 (14)	0.0270 (15)	0.020 (2)	−0.0012 (12)	0.0070 (14)	−0.0046 (14)
C12	0.0213 (15)	0.0362 (18)	0.0130 (19)	−0.0070 (14)	0.0048 (14)	−0.0006 (15)
C13	0.0138 (13)	0.0168 (14)	0.022 (2)	0.0024 (11)	0.0030 (13)	−0.0015 (14)
C14	0.0342 (19)	0.043 (2)	0.029 (3)	−0.0029 (17)	0.0004 (19)	0.0153 (19)
C15	0.039 (2)	0.062 (3)	0.040 (3)	−0.011 (2)	0.018 (2)	−0.026 (2)
C16	0.0134 (13)	0.0208 (14)	0.0194 (19)	−0.0005 (11)	0.0047 (13)	−0.0009 (13)
C17	0.0215 (15)	0.0241 (15)	0.024 (2)	0.0028 (13)	0.0083 (16)	0.0011 (14)
C18	0.0181 (14)	0.0180 (14)	0.0123 (18)	−0.0009 (11)	0.0049 (14)	−0.0020 (12)
C19	0.0217 (15)	0.0247 (15)	0.021 (2)	0.0018 (13)	0.0055 (15)	0.0009 (14)
C20	0.0202 (15)	0.0239 (16)	0.030 (2)	0.0010 (13)	0.0032 (16)	0.0024 (15)
C21	0.0273 (17)	0.0215 (15)	0.018 (2)	−0.0019 (13)	−0.0061 (16)	0.0020 (14)
C22	0.0336 (19)	0.0255 (16)	0.020 (2)	0.0025 (14)	0.0090 (17)	0.0019 (15)
C23	0.0256 (16)	0.0247 (15)	0.0153 (19)	0.0011 (13)	0.0087 (15)	0.0014 (14)
C24	0.041 (2)	0.0337 (19)	0.021 (2)	−0.0005 (16)	−0.0092 (19)	0.0051 (18)

Geometric parameters (Å, º) top

S1—O10	1.427 (2)	C8—H8A	0.9700
S1—O9	1.428 (2)	C8—H8B	0.9700
S1—O8	1.602 (2)	C9—C10	1.524 (4)
S1—C18	1.741 (4)	C9—H9	0.9800
S2—O2	1.427 (3)	C10—C11	1.521 (4)
S2—O1	1.428 (2)	C10—H10	0.9800
S2—O3	1.578 (2)	C11—C13	1.539 (4)
S2—C1	1.743 (4)	C11—H11	0.9800
N1—C17	1.139 (5)	C12—C14	1.494 (5)
O3—C8	1.467 (3)	C12—C15	1.512 (5)
O4—C13	1.423 (4)	C13—C16	1.530 (4)
O4—C9	1.454 (3)	C14—H14A	0.9600
O5—C10	1.406 (4)	C14—H14B	0.9600
O5—H5	0.8200	C14—H14C	0.9600
O6—C11	1.415 (4)	C15—H15A	0.9600
O6—C12	1.431 (4)	C15—H15B	0.9600
O7—C13	1.396 (4)	C15—H15C	0.9600
O7—C12	1.438 (4)	C16—C17	1.483 (5)
O8—C16	1.450 (3)	C16—H16	0.9800
C1—C6	1.383 (4)	C18—C19	1.388 (4)
C1—C2	1.401 (5)	C18—C23	1.391 (5)
C2—C3	1.390 (6)	C19—C20	1.399 (5)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.396 (5)	C20—C21	1.394 (5)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.388 (6)	C21—C22	1.394 (5)
C4—C7	1.499 (6)	C21—C24	1.506 (5)
C5—C6	1.386 (6)	C22—C23	1.389 (5)
C5—H5A	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—H23	0.9300
C7—H7A	0.9600	C24—H24A	0.9600
C7—H7B	0.9600	C24—H24B	0.9600
C7—H7C	0.9600	C24—H24C	0.9600
C8—C9	1.488 (5)

O10—S1—O9	120.29 (15)	O6—C11—C13	102.7 (2)
O10—S1—O8	102.76 (13)	C10—C11—C13	104.9 (3)
O9—S1—O8	108.47 (13)	O6—C11—H11	112.9
O10—S1—C18	110.50 (14)	C10—C11—H11	112.9
O9—S1—C18	109.72 (15)	C13—C11—H11	112.9
O8—S1—C18	103.57 (14)	O6—C12—O7	104.5 (3)
O2—S2—O1	119.71 (16)	O6—C12—C14	109.8 (3)
O2—S2—O3	109.48 (13)	O7—C12—C14	108.2 (3)
O1—S2—O3	103.49 (13)	O6—C12—C15	111.1 (3)
O2—S2—C1	109.25 (16)	O7—C12—C15	109.3 (3)
O1—S2—C1	109.28 (16)	C14—C12—C15	113.5 (4)
O3—S2—C1	104.48 (15)	O7—C13—O4	111.5 (2)
C8—O3—S2	118.17 (19)	O7—C13—C16	108.0 (2)
C13—O4—C9	110.4 (2)	O4—C13—C16	108.1 (3)
C10—O5—H5	109.5	O7—C13—C11	105.6 (3)
C11—O6—C12	108.3 (3)	O4—C13—C11	105.7 (2)
C13—O7—C12	110.1 (2)	C16—C13—C11	117.9 (2)
C16—O8—S1	118.35 (17)	C12—C14—H14A	109.5
C6—C1—C2	119.9 (4)	C12—C14—H14B	109.5
C6—C1—S2	121.6 (3)	H14A—C14—H14B	109.5
C2—C1—S2	118.5 (3)	C12—C14—H14C	109.5
C3—C2—C1	119.6 (3)	H14A—C14—H14C	109.5
C3—C2—H2	120.2	H14B—C14—H14C	109.5
C1—C2—H2	120.2	C12—C15—H15A	109.5
C2—C3—C4	120.8 (4)	C12—C15—H15B	109.5
C2—C3—H3	119.6	H15A—C15—H15B	109.5
C4—C3—H3	119.6	C12—C15—H15C	109.5
C5—C4—C3	118.6 (4)	H15A—C15—H15C	109.5
C5—C4—C7	121.1 (4)	H15B—C15—H15C	109.5
C3—C4—C7	120.4 (4)	O8—C16—C17	107.9 (3)
C6—C5—C4	121.3 (3)	O8—C16—C13	106.4 (2)
C6—C5—H5A	119.3	C17—C16—C13	113.7 (3)
C4—C5—H5A	119.3	O8—C16—H16	109.6
C1—C6—C5	119.8 (3)	C17—C16—H16	109.6
C1—C6—H6	120.1	C13—C16—H16	109.6
C5—C6—H6	120.1	N1—C17—C16	177.1 (4)
C4—C7—H7A	109.5	C19—C18—C23	122.0 (3)
C4—C7—H7B	109.5	C19—C18—S1	119.2 (3)
H7A—C7—H7B	109.5	C23—C18—S1	118.6 (2)
C4—C7—H7C	109.5	C18—C19—C20	117.5 (3)
H7A—C7—H7C	109.5	C18—C19—H19	121.2
H7B—C7—H7C	109.5	C20—C19—H19	121.2
O3—C8—C9	108.9 (3)	C21—C20—C19	122.1 (3)
O3—C8—H8A	109.9	C21—C20—H20	119.0
C9—C8—H8A	109.9	C19—C20—H20	119.0
O3—C8—H8B	109.9	C22—C21—C20	118.4 (3)
C9—C8—H8B	109.9	C22—C21—C24	120.6 (4)
H8A—C8—H8B	108.3	C20—C21—C24	121.0 (3)
O4—C9—C8	108.1 (3)	C23—C22—C21	120.9 (4)
O4—C9—C10	104.0 (2)	C23—C22—H22	119.5
C8—C9—C10	114.5 (3)	C21—C22—H22	119.5
O4—C9—H9	110.0	C22—C23—C18	119.0 (3)
C8—C9—H9	110.0	C22—C23—H23	120.5
C10—C9—H9	110.0	C18—C23—H23	120.5
O5—C10—C11	111.3 (3)	C21—C24—H24A	109.5
O5—C10—C9	108.5 (3)	C21—C24—H24B	109.5
C11—C10—C9	101.6 (2)	H24A—C24—H24B	109.5
O5—C10—H10	111.6	C21—C24—H24C	109.5
C11—C10—H10	111.6	H24A—C24—H24C	109.5
C9—C10—H10	111.6	H24B—C24—H24C	109.5
O6—C11—C10	109.7 (3)

O2—S2—O3—C8	33.2 (3)	C13—O7—C12—O6	−16.2 (3)
O1—S2—O3—C8	161.9 (3)	C13—O7—C12—C14	−133.2 (3)
C1—S2—O3—C8	−83.7 (3)	C13—O7—C12—C15	102.7 (3)
O10—S1—O8—C16	−166.0 (2)	C12—O7—C13—O4	112.8 (3)
O9—S1—O8—C16	−37.6 (3)	C12—O7—C13—C16	−128.6 (3)
C18—S1—O8—C16	78.9 (3)	C12—O7—C13—C11	−1.6 (3)
O2—S2—C1—C6	−12.2 (3)	C9—O4—C13—O7	−105.8 (3)
O1—S2—C1—C6	−144.9 (3)	C9—O4—C13—C16	135.5 (3)
O3—S2—C1—C6	104.8 (3)	C9—O4—C13—C11	8.4 (3)
O2—S2—C1—C2	168.0 (3)	O6—C11—C13—O7	18.8 (3)
O1—S2—C1—C2	35.3 (3)	C10—C11—C13—O7	133.5 (3)
O3—S2—C1—C2	−75.0 (3)	O6—C11—C13—O4	−99.5 (3)
C6—C1—C2—C3	0.8 (5)	C10—C11—C13—O4	15.2 (3)
S2—C1—C2—C3	−179.4 (3)	O6—C11—C13—C16	139.6 (3)
C1—C2—C3—C4	−0.3 (6)	C10—C11—C13—C16	−105.7 (3)
C2—C3—C4—C5	0.1 (6)	S1—O8—C16—C17	−92.6 (3)
C2—C3—C4—C7	179.0 (4)	S1—O8—C16—C13	145.0 (2)
C3—C4—C5—C6	−0.3 (6)	O7—C13—C16—O8	−48.4 (3)
C7—C4—C5—C6	−179.2 (4)	O4—C13—C16—O8	72.5 (3)
C2—C1—C6—C5	−1.0 (5)	C11—C13—C16—O8	−167.8 (3)
S2—C1—C6—C5	179.2 (3)	O7—C13—C16—C17	−167.0 (3)
C4—C5—C6—C1	0.8 (6)	O4—C13—C16—C17	−46.2 (3)
S2—O3—C8—C9	−100.7 (3)	C11—C13—C16—C17	73.5 (4)
C13—O4—C9—C8	−150.7 (2)	O10—S1—C18—C19	147.6 (3)
C13—O4—C9—C10	−28.7 (3)	O9—S1—C18—C19	12.7 (3)
O3—C8—C9—O4	−67.9 (3)	O8—S1—C18—C19	−103.0 (3)
O3—C8—C9—C10	176.7 (3)	O10—S1—C18—C23	−36.9 (3)
O4—C9—C10—O5	−81.1 (3)	O9—S1—C18—C23	−171.8 (2)
C8—C9—C10—O5	36.6 (4)	O8—S1—C18—C23	72.5 (3)
O4—C9—C10—C11	36.3 (3)	C23—C18—C19—C20	0.7 (5)
C8—C9—C10—C11	154.0 (3)	S1—C18—C19—C20	176.0 (2)
C12—O6—C11—C10	−140.6 (3)	C18—C19—C20—C21	−0.9 (5)
C12—O6—C11—C13	−29.4 (3)	C19—C20—C21—C22	0.6 (5)
O5—C10—C11—O6	−166.2 (2)	C19—C20—C21—C24	−179.1 (3)
C9—C10—C11—O6	78.4 (3)	C20—C21—C22—C23	−0.2 (5)
O5—C10—C11—C13	84.1 (3)	C24—C21—C22—C23	179.5 (3)
C9—C10—C11—C13	−31.3 (3)	C21—C22—C23—C18	0.0 (5)
C11—O6—C12—O7	29.1 (3)	C19—C18—C23—C22	−0.3 (5)
C11—O6—C12—C14	145.0 (3)	S1—C18—C23—C22	−175.7 (3)
C11—O6—C12—C15	−88.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4ⁱ	0.82	2.03	2.844 (3)	169

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₇NO₁₀S₂
M_r	553.59
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	5.6342 (11), 28.771 (6), 8.3226 (17)
β (°)	103.00 (3)
V (Å³)	1314.5 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.16 × 0.12 × 0.08

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.960, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	8980, 4781, 4228
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.127, 1.05
No. of reflections	4781
No. of parameters	339
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.51
Absolute structure	Flack (1983), 1570 Friedel pairs
Absolute structure parameter	0.07 (7)

Computer programs: CrystalClear (Rigaku, 2005), 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
O5—H5···O4ⁱ	0.82	2.03	2.844 (3)	168.7

Symmetry code: (i) x+1, y, z.

Acknowledgements

We acknowledge financial support from the National Natural Science Foundation of China.

References

Bianchi, P., Roda, G., Riva, S., Danieli, B., Zabelinskaja-Mackova, A. & Griengl, H. (2001). Tetrahedron, 57, 2213–2220. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Georges, M. & Fraser-Reid, B. (1984). Carbohydr. Res. 127, 162–164. CrossRef CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sharma, G. V. M., Begum, A., Reddy, K. R., Sankar, A. R. & Kunwar, A. C. (2003). Tetrahedron Asymmetry, 14, 3899–3905. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szarek, M. A., Wu, X. F. & Szarek, W. A. (1997). Carbohydr. Res. 299, 165–170. CrossRef CAS Web of Science Google Scholar

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Volume 65| Part 10| October 2009| Page o2437

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

3,4-O-Iso­propyl­­idene-2,7-di-O-p-tolyl­sulfonyl-α-L-xylo-3-heptulo-3,6-furan­osono­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,4-O-Isopropylidene-2,7-di-O-p-tolylsulfonyl-α-L-xylo-3-heptulo-3,6-furanosononitrile