Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-de­oxy-1-thio-β-d-glucopyran­oside

Manabe, S.; Ishii, K.; Hashizume, D.; Ito, Y.

doi:10.1107/S1600536808027189

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1868

doi:10.1107/S1600536808027189

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Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside

Shino Manabe,^a ^* Kazuyuki Ishii,^a Daisuke Hashizume ^b and Yukishige Ito ^a

^aAdvanced Science Institute, RIKEN (The Institute of Physical and Chemical Research), Hirosawa, Wako, Saitama 351-0198, Japan, and ^bAdvanced Technology Support Division, RIKEN (The Institute of Physical and Chemical Research), Hirosawa, Wako, Saitama 351-0198, Japan
^*Correspondence e-mail: smanabe@riken.jp

(Received 11 August 2008; accepted 23 August 2008; online 6 September 2008)

In the crystal structure of the title compound, C₂₇H₂₇NO₅S, the pyranose ring adopts a ⁴C₁ chair conformation with puckering parameters Q = 0.639 (2) Å, θ = 174.11 (18) and φ = 256 (2)°. The presence of the 2,3-trans-oxazolidinone fixes the conformation of the pyranose ring. The phenyl group attached to the S atom and the benzyl group bonding to the N atom are each disordered over two positions with site occupancies of 0.624 (3):0.376 (3) and 0.526 (3):0.474 (3), respectively. An intermolecular O—H⋯O hydrogen bond is observed.

Related literature

For related literature, see: Benakli et al. (2001 ); Boysen et al. (2005 ); Cremer & Pople (1975 ); Crich & Vinod (2005 ); Geng et al. (2008 ); Manabe et al. (2006 ); Satoh et al. (2008 ).

Experimental

Crystal data

C₂₇H₂₇NO₅S
M_r = 477.56
Monoclinic, P 2₁
a = 13.8166 (7) Å
b = 5.7008 (3) Å
c = 15.0425 (9) Å
β = 91.494 (4)°
V = 1184.43 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 90 K
0.30 × 0.08 × 0.07 mm

Data collection

Rigaku AFC8 diffractometer with Saturn70 CCD
Absorption correction: multi-scan (MULABS; Blessing, 1995 ) T_min = 0.959, T_max = 0.998
7074 measured reflections
4965 independent reflections
3970 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.167
S = 1.03
4965 reflections
353 parameters
31 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ), 1983 Friedel pairs
Flack parameter: 0.05 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O5ⁱ	0.84	1.98	2.774 (2)	158
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear SM (Rigaku/MSC, 2005 ); cell refinement: HKL-2000 (Otwinowski & Minor, 1997 ); data reduction: HKL-2000; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027189/is2324sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027189/is2324Isup2.hkl

checkCIF report

Comment top

Recently, we and other groups reported 2,3-trans-oxazolidinone carrying novel glycosyl donors for α-selective glycosylation (Benakli et al., 2001; Boysen et al., 2005; Crich & Vinod, 2005; Manabe et al., 2006; Geng et al., 2008). Furthermore, we also found the 2,3-trans-oxazolidinone carrying pyranoses are easily anomerized via an endo-cleavage manner (Manabe et al., 2006; Satoh et al., 2008). In order to investigate the origin of the high stereosetectivity and its unique character, we are interested in the conformation of the pyranose ring with 2,3-trans-oxazolidinone group.

The pyranose ring of the title compound adapts a ⁴C₁ chair conformation. The torsion angles (O1—C1—C2—C3, C1—C2—C3—C4, C2—C3—C4—C5, C3—C4—C5—O1, C4—C5—O1—C1 and C5—O1—C1—C2; see geometric parameters table in supplementary materials) and Cremer-Pople puckering parameters (Cremer & Pople, 1975), Q = 0.639 (2) Å, θ = 174.11 (18)° and ϕ = 256 (2)°, of the ring clearly indicate the ⁴C₁ conformation.

Related literature top

For related literature, see: Benakli et al. (2001); Boysen et al. (2005); Cremer & Pople (1975); Crich & Vinod (2005); Geng et al. (2008); Manabe et al. (2006); Satoh et al. (2008).

Experimental top

The compound, (I), was prepared as described by Benakli et al. (2001). (I) was dissolved in ethyl acetate at room temperature and hexane was added. The solution was kept at room temperature in a sealed flask for a few days to give single crystals suitable for single-crystal X-ray analysis.

Computing details top

Data collection: CrystalClear SM (Rigaku/MSC, 2005); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of (I), showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. The minor parts of the disordered phenyl moieties are omitted for clarity.

Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside top

Crystal data top

C₂₇H₂₇NO₅S	F(000) = 504
M_r = 477.56	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7082 reflections
a = 13.8166 (7) Å	θ = 1.4–27.5°
b = 5.7008 (3) Å	µ = 0.18 mm⁻¹
c = 15.0425 (9) Å	T = 90 K
β = 91.494 (4)°	Needle, colourless
V = 1184.43 (11) Å³	0.30 × 0.08 × 0.07 mm
Z = 2

Data collection top

Rigaku AFC8 diffractometer with Saturn70 CCD	4965 independent reflections
Radiation source: fine-focus rotating anode	3970 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.040
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 1.4°
ω–scan	h = −17→15
Absorption correction: multi-scan (MULABS; Blessing, 1995)	k = −7→6
T_min = 0.959, T_max = 0.998	l = −19→19
7074 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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0942P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.011
4965 reflections	Δρ_max = 0.33 e Å⁻³
353 parameters	Δρ_min = −0.34 e Å⁻³
31 restraints	Absolute structure: Flack (1983), 1983 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (11)

Crystal data top

C₂₇H₂₇NO₅S	V = 1184.43 (11) Å³
M_r = 477.56	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 13.8166 (7) Å	µ = 0.18 mm⁻¹
b = 5.7008 (3) Å	T = 90 K
c = 15.0425 (9) Å	0.30 × 0.08 × 0.07 mm
β = 91.494 (4)°

Data collection top

Rigaku AFC8 diffractometer with Saturn70 CCD	4965 independent reflections
Absorption correction: multi-scan (MULABS; Blessing, 1995)	3970 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.998	R_int = 0.040
7074 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.167	Δρ_max = 0.33 e Å⁻³
S = 1.03	Δρ_min = −0.34 e Å⁻³
4965 reflections	Absolute structure: Flack (1983), 1983 Friedel pairs
353 parameters	Absolute structure parameter: 0.05 (11)
31 restraints

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 > 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	Occ. (<1)
S1	0.34405 (4)	0.61596 (13)	0.35271 (4)	0.03602 (14)
O1	0.16119 (10)	0.6528 (3)	0.30101 (9)	0.0265 (3)
O2	0.07008 (11)	0.0779 (3)	0.44133 (9)	0.0280 (4)
O3	−0.06858 (11)	0.3322 (3)	0.31331 (10)	0.0294 (4)
H3O	−0.1054	0.3031	0.3555	0.035*
O4	0.05569 (11)	0.9160 (3)	0.17927 (9)	0.0272 (4)
O5	0.16411 (12)	−0.1618 (3)	0.52679 (10)	0.0333 (4)
N1	0.22987 (13)	0.1425 (3)	0.44686 (11)	0.0266 (4)
C1	0.23048 (16)	0.4742 (4)	0.32615 (15)	0.0268 (5)
H1	0.2383	0.3602	0.2763	0.032*
C2	0.18671 (15)	0.3529 (4)	0.40565 (13)	0.0245 (5)
H2	0.1728	0.4714	0.4526	0.029*
C3	0.09332 (16)	0.2431 (4)	0.37230 (13)	0.0254 (5)
H3	0.1076	0.1517	0.3174	0.030*
C4	0.01933 (15)	0.4275 (4)	0.34745 (13)	0.0247 (5)
H4	0.0072	0.5329	0.3991	0.030*
C5	0.06745 (15)	0.5641 (4)	0.27204 (13)	0.0240 (5)
H5	0.0760	0.4565	0.2203	0.029*
C6	0.00733 (16)	0.7723 (4)	0.24210 (14)	0.0259 (5)
H61	−0.0544	0.7155	0.2149	0.031*
H62	−0.0084	0.8683	0.2946	0.031*
C7	0.15701 (17)	0.0048 (4)	0.47591 (14)	0.0293 (5)
C8A	0.39021 (14)	0.6625 (6)	0.24481 (13)	0.0433 (7)	0.624 (3)
C9A	0.3372 (2)	0.7700 (7)	0.17667 (14)	0.0450 (10)	0.624 (3)
H9A	0.2725	0.8185	0.1862	0.054*	0.624 (3)
C10A	0.37834 (16)	0.8070 (8)	0.09447 (18)	0.0571 (11)	0.624 (3)
H10A	0.3428	0.8712	0.0453	0.068*	0.624 (3)
C11A	0.47501 (18)	0.7437 (8)	0.0892 (2)	0.0800 (12)	0.624 (3)
H11A	0.5053	0.7669	0.0339	0.096*	0.624 (3)
C12A	0.5310 (2)	0.6490 (10)	0.15830 (17)	0.094 (2)	0.624 (3)
H12A	0.5972	0.6115	0.1502	0.113*	0.624 (3)
C13A	0.48825 (16)	0.6104 (10)	0.2395 (2)	0.0628 (13)	0.624 (3)
H13A	0.5243	0.5510	0.2892	0.075*	0.624 (3)
C8B	0.3898 (2)	0.6505 (5)	0.24391 (14)	0.0433 (7)	0.376 (3)
C9B	0.3554 (3)	0.8270 (7)	0.18792 (19)	0.0450 (10)	0.376 (3)
H9B	0.3031	0.9236	0.2052	0.054*	0.376 (3)
C10B	0.3982 (3)	0.8608 (9)	0.1063 (2)	0.0571 (11)	0.376 (3)
H10B	0.3778	0.9961	0.0740	0.068*	0.376 (3)
C11B	0.4669 (4)	0.7218 (6)	0.0659 (3)	0.0800 (12)	0.376 (3)
H11B	0.4979	0.7616	0.0124	0.096*	0.376 (3)
C12B	0.4845 (4)	0.5173 (8)	0.1138 (2)	0.094 (2)	0.376 (3)
H12B	0.5231	0.3964	0.0896	0.113*	0.376 (3)
C13B	0.4453 (3)	0.4903 (8)	0.1974 (2)	0.0628 (13)	0.376 (3)
H13B	0.4580	0.3449	0.2263	0.075*	0.376 (3)
C14	0.323625 (11)	0.13833 (2)	0.49395 (2)	0.0290 (5)
H141	0.3748	0.1717	0.4509	0.035*
H142	0.3350	−0.0217	0.5175	0.035*
C15A	0.333196 (11)	0.31100 (2)	0.56988 (2)	0.0311 (5)	0.526 (3)
C16A	0.410308 (11)	0.46761 (2)	0.56994 (2)	0.0464 (11)	0.526 (3)
H16A	0.4574	0.4574	0.5252	0.056*	0.526 (3)
C17A	0.4187 (2)	0.6396 (6)	0.63559 (18)	0.0654 (15)	0.526 (3)
H17A	0.4742	0.7381	0.6368	0.078*	0.526 (3)
C18A	0.34885 (18)	0.6723 (6)	0.6995 (2)	0.0455 (12)	0.526 (3)
H18A	0.3538	0.7955	0.7419	0.055*	0.526 (3)
C19A	0.2716 (2)	0.5160 (5)	0.6983 (2)	0.0371 (7)	0.526 (3)
H19A	0.2237	0.5283	0.7422	0.045*	0.526 (3)
C20A	0.2633 (2)	0.3421 (6)	0.63375 (17)	0.0306 (5)	0.526 (3)
H20A	0.2084	0.2417	0.6332	0.037*	0.526 (3)
C15B	0.33272 (2)	0.30995 (3)	0.57017 (3)	0.0311 (5)	0.474 (3)
C16B	0.42307 (17)	0.4031 (7)	0.5928 (2)	0.0464 (11)	0.474 (3)
H16B	0.4764	0.3710	0.5561	0.056*	0.474 (3)
C17B	0.4369 (2)	0.5420 (9)	0.6679 (2)	0.0654 (15)	0.474 (3)
H17B	0.4978	0.6131	0.6812	0.078*	0.474 (3)
C18B	0.35861 (16)	0.5736 (9)	0.7230 (3)	0.0455 (12)	0.474 (3)
H18B	0.3673	0.6613	0.7763	0.055*	0.474 (3)
C19B	0.2680 (2)	0.4799 (6)	0.7020 (2)	0.0371 (7)	0.474 (3)
H19B	0.2147	0.5114	0.7388	0.045*	0.474 (3)
C20B	0.25570 (19)	0.3397 (8)	0.62686 (19)	0.0306 (5)	0.474 (3)
H20B	0.1954	0.2652	0.6144	0.037*	0.474 (3)
C21	0.0574 (2)	0.8149 (4)	0.09276 (14)	0.0355 (6)
H211	−0.0091	0.8092	0.0667	0.043*
H212	0.0824	0.6525	0.0967	0.043*
C22	0.12116 (17)	0.9594 (4)	0.03426 (14)	0.0297 (5)
C23	0.13491 (18)	0.8889 (5)	−0.05315 (14)	0.0359 (6)
H23	0.1038	0.7511	−0.0749	0.043*
C24	0.1933 (2)	1.0167 (5)	−0.10881 (16)	0.0434 (7)
H24	0.2033	0.9649	−0.1679	0.052*
C25	0.2369 (2)	1.2195 (6)	−0.07797 (18)	0.0572 (9)
H25	0.2758	1.3094	−0.1164	0.069*
C26	0.2243 (2)	1.2937 (6)	0.0092 (2)	0.0610 (9)
H26	0.2543	1.4335	0.0304	0.073*
C27	0.1669 (2)	1.1598 (5)	0.06496 (15)	0.0405 (7)
H27	0.1592	1.2074	0.1249	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0211 (2)	0.0387 (3)	0.0481 (3)	−0.0025 (3)	−0.0012 (2)	0.0103 (3)
O1	0.0172 (6)	0.0286 (7)	0.0336 (7)	−0.0016 (6)	0.0000 (6)	0.0039 (6)
O2	0.0292 (7)	0.0257 (8)	0.0292 (7)	−0.0036 (6)	0.0067 (6)	0.0029 (6)
O3	0.0201 (7)	0.0382 (8)	0.0299 (7)	−0.0081 (7)	0.0018 (6)	−0.0026 (7)
O4	0.0296 (8)	0.0303 (7)	0.0216 (6)	−0.0015 (7)	0.0019 (6)	−0.0008 (6)
O5	0.0404 (9)	0.0290 (8)	0.0311 (7)	0.0043 (7)	0.0105 (7)	0.0035 (6)
N1	0.0280 (9)	0.0252 (8)	0.0268 (8)	0.0022 (8)	0.0026 (7)	0.0008 (7)
C1	0.0191 (10)	0.0263 (10)	0.0350 (11)	0.0010 (9)	0.0003 (9)	0.0046 (9)
C2	0.0233 (10)	0.0238 (10)	0.0264 (9)	−0.0009 (9)	0.0026 (8)	−0.0017 (8)
C3	0.0256 (10)	0.0274 (10)	0.0235 (9)	−0.0059 (9)	0.0064 (8)	−0.0023 (8)
C4	0.0214 (10)	0.0303 (10)	0.0224 (9)	−0.0066 (9)	0.0024 (8)	−0.0031 (8)
C5	0.0201 (9)	0.0282 (11)	0.0238 (9)	−0.0028 (8)	0.0004 (8)	−0.0008 (8)
C6	0.0203 (10)	0.0303 (11)	0.0270 (10)	−0.0034 (9)	0.0003 (9)	0.0005 (8)
C7	0.0348 (12)	0.0273 (10)	0.0263 (10)	0.0019 (10)	0.0079 (9)	−0.0019 (8)
C8A	0.0235 (11)	0.0399 (13)	0.0672 (15)	0.0004 (11)	0.0129 (11)	0.0111 (12)
C9A	0.0326 (17)	0.060 (2)	0.0426 (15)	−0.0028 (18)	0.0067 (14)	−0.0048 (16)
C10A	0.059 (2)	0.069 (3)	0.0444 (16)	−0.024 (2)	0.0153 (17)	−0.0122 (18)
C11A	0.085 (2)	0.078 (2)	0.080 (2)	−0.016 (2)	0.0654 (18)	−0.004 (2)
C12A	0.044 (2)	0.116 (5)	0.125 (4)	0.012 (3)	0.049 (2)	0.001 (4)
C13A	0.0211 (17)	0.092 (3)	0.076 (3)	0.001 (2)	0.0054 (17)	0.002 (3)
C8B	0.0235 (11)	0.0399 (13)	0.0672 (15)	0.0004 (11)	0.0129 (11)	0.0111 (12)
C9B	0.0326 (17)	0.060 (2)	0.0426 (15)	−0.0028 (18)	0.0067 (14)	−0.0048 (16)
C10B	0.059 (2)	0.069 (3)	0.0444 (16)	−0.024 (2)	0.0153 (17)	−0.0122 (18)
C11B	0.085 (2)	0.078 (2)	0.080 (2)	−0.016 (2)	0.0654 (18)	−0.004 (2)
C12B	0.044 (2)	0.116 (5)	0.125 (4)	0.012 (3)	0.049 (2)	0.001 (4)
C13B	0.0211 (17)	0.092 (3)	0.076 (3)	0.001 (2)	0.0054 (17)	0.002 (3)
C14	0.0238 (9)	0.0316 (11)	0.0317 (10)	0.0071 (10)	0.0045 (8)	0.0026 (10)
C15A	0.0252 (11)	0.0408 (12)	0.0271 (10)	0.0066 (10)	−0.0008 (9)	0.0045 (9)
C16A	0.0222 (14)	0.095 (3)	0.0218 (16)	−0.0046 (18)	−0.0064 (13)	−0.003 (2)
C17A	0.0294 (17)	0.134 (4)	0.033 (2)	−0.021 (2)	−0.0030 (17)	−0.025 (2)
C18A	0.0459 (18)	0.061 (3)	0.0296 (17)	−0.009 (2)	0.0044 (15)	−0.0054 (18)
C19A	0.0285 (12)	0.0524 (17)	0.0306 (11)	−0.0031 (12)	0.0037 (10)	−0.0021 (11)
C20A	0.0249 (11)	0.0373 (12)	0.0296 (11)	0.0044 (10)	−0.0006 (10)	0.0028 (10)
C15B	0.0252 (11)	0.0408 (12)	0.0271 (10)	0.0066 (10)	−0.0008 (9)	0.0045 (9)
C16B	0.0222 (14)	0.095 (3)	0.0218 (16)	−0.0046 (18)	−0.0064 (13)	−0.003 (2)
C17B	0.0294 (17)	0.134 (4)	0.033 (2)	−0.021 (2)	−0.0030 (17)	−0.025 (2)
C18B	0.0459 (18)	0.061 (3)	0.0296 (17)	−0.009 (2)	0.0044 (15)	−0.0054 (18)
C19B	0.0285 (12)	0.0524 (17)	0.0306 (11)	−0.0031 (12)	0.0037 (10)	−0.0021 (11)
C20B	0.0249 (11)	0.0373 (12)	0.0296 (11)	0.0044 (10)	−0.0006 (10)	0.0028 (10)
C21	0.0492 (14)	0.0344 (11)	0.0231 (10)	−0.0067 (11)	0.0037 (10)	−0.0035 (9)
C22	0.0289 (11)	0.0328 (11)	0.0275 (10)	0.0072 (10)	0.0006 (9)	0.0023 (9)
C23	0.0359 (12)	0.0443 (13)	0.0275 (10)	0.0135 (11)	0.0000 (10)	0.0008 (10)
C24	0.0365 (13)	0.0675 (16)	0.0263 (11)	0.0197 (13)	0.0039 (10)	0.0069 (11)
C25	0.0511 (17)	0.087 (2)	0.0340 (13)	−0.0145 (17)	0.0034 (13)	0.0172 (14)
C26	0.068 (2)	0.0681 (19)	0.0474 (15)	−0.0265 (17)	0.0064 (15)	0.0103 (14)
C27	0.0449 (14)	0.0462 (14)	0.0305 (11)	−0.0062 (12)	0.0009 (11)	0.0041 (11)

Geometric parameters (Å, º) top

S1—C8A	1.7791 (19)	C11B—H11B	0.9500
S1—C8B	1.781 (2)	C12B—C13B	1.390 (3)
S1—C1	1.801 (2)	C12B—H12B	0.9500
O1—C1	1.441 (3)	C13B—H13B	0.9500
O1—C5	1.447 (2)	C14—C15B	1.5099 (4)
O2—C7	1.362 (3)	C14—C15A	1.5110 (4)
O2—C3	1.444 (2)	C14—H141	0.9900
O3—C4	1.415 (3)	C14—H142	0.9900
O3—H3O	0.8400	C15A—C16A	1.3900 (2)
O4—C21	1.424 (3)	C15A—C20A	1.391 (2)
O4—C6	1.430 (3)	C16A—C17A	1.394 (2)
O5—C7	1.222 (3)	C16A—H16A	0.9500
N1—C7	1.358 (3)	C17A—C18A	1.393 (3)
N1—C14	1.4604 (18)	C17A—H17A	0.9500
N1—C2	1.470 (3)	C18A—C19A	1.390 (3)
C1—C2	1.520 (3)	C18A—H18A	0.9500
C1—H1	1.0000	C19A—C20A	1.390 (3)
C2—C3	1.508 (3)	C19A—H19A	0.9500
C2—H2	1.0000	C20A—H20A	0.9500
C3—C4	1.507 (3)	C15B—C16B	1.391 (2)
C3—H3	1.0000	C15B—C20B	1.391 (2)
C4—C5	1.541 (3)	C16B—C17B	1.389 (3)
C4—H4	1.0000	C16B—H16B	0.9500
C5—C6	1.511 (3)	C17B—C18B	1.391 (3)
C5—H5	1.0000	C17B—H17B	0.9500
C6—H61	0.9900	C18B—C19B	1.390 (3)
C6—H62	0.9900	C18B—H18B	0.9500
C8A—C9A	1.387 (2)	C19B—C20B	1.390 (3)
C8A—C13A	1.391 (2)	C19B—H19B	0.9500
C9A—C10A	1.390 (2)	C20B—H20B	0.9500
C9A—H9A	0.9500	C21—C22	1.507 (3)
C10A—C11A	1.388 (2)	C21—H211	0.9900
C10A—H10A	0.9500	C21—H212	0.9900
C11A—C12A	1.388 (3)	C22—C27	1.379 (3)
C11A—H11A	0.9500	C22—C23	1.393 (3)
C12A—C13A	1.388 (3)	C23—C24	1.385 (4)
C12A—H12A	0.9500	C23—H23	0.9500
C13A—H13A	0.9500	C24—C25	1.379 (4)
C8B—C9B	1.388 (3)	C24—H24	0.9500
C8B—C13B	1.393 (3)	C25—C26	1.393 (4)
C9B—C10B	1.390 (3)	C25—H25	0.9500
C9B—H9B	0.9500	C26—C27	1.397 (4)
C10B—C11B	1.389 (3)	C26—H26	0.9500
C10B—H10B	0.9500	C27—H27	0.9500
C11B—C12B	1.389 (3)

C8A—S1—C1	101.28 (11)	C9B—C10B—H10B	115.9
C8B—S1—C1	100.03 (13)	C10B—C11B—C12B	111.4 (4)
C1—O1—C5	114.53 (15)	C10B—C11B—H11B	124.3
C7—O2—C3	105.30 (16)	C12B—C11B—H11B	124.3
C4—O3—H3O	109.5	C11B—C12B—C13B	119.7 (4)
C21—O4—C6	113.05 (17)	C11B—C12B—H12B	120.2
C7—N1—C14	119.35 (15)	C13B—C12B—H12B	120.2
C7—N1—C2	108.16 (17)	C12B—C13B—C8B	127.9 (4)
C14—N1—C2	124.26 (15)	C12B—C13B—H13B	116.1
O1—C1—C2	104.63 (16)	C8B—C13B—H13B	116.1
O1—C1—S1	108.08 (14)	N1—C14—C15B	114.39 (7)
C2—C1—S1	113.07 (15)	N1—C14—C15A	114.53 (7)
O1—C1—H1	110.3	N1—C14—H141	108.6
C2—C1—H1	110.3	N1—C14—H142	108.6
S1—C1—H1	110.3	C16A—C15A—C20A	117.64 (13)
N1—C2—C3	97.80 (16)	C16A—C15A—C14	118.1
N1—C2—C1	122.53 (17)	C20A—C15A—C14	123.79 (12)
C3—C2—C1	106.35 (17)	C15A—C16A—C17A	120.10 (12)
N1—C2—H2	109.7	C15A—C16A—H16A	119.9
C3—C2—H2	109.7	C17A—C16A—H16A	119.9
C1—C2—H2	109.7	C18A—C17A—C16A	122.5 (3)
O2—C3—C4	118.12 (17)	C18A—C17A—H17A	118.8
O2—C3—C2	103.64 (16)	C16A—C17A—H17A	118.8
C4—C3—C2	111.22 (17)	C19A—C18A—C17A	116.8 (3)
O2—C3—H3	107.8	C19A—C18A—H18A	121.6
C4—C3—H3	107.8	C17A—C18A—H18A	121.6
C2—C3—H3	107.8	C18A—C19A—C20A	121.1 (3)
O3—C4—C3	113.12 (17)	C18A—C19A—H19A	119.5
O3—C4—C5	108.03 (16)	C20A—C19A—H19A	119.5
C3—C4—C5	103.43 (16)	C19A—C20A—C15A	121.8 (3)
O3—C4—H4	110.7	C19A—C20A—H20A	119.1
C3—C4—H4	110.7	C15A—C20A—H20A	119.1
C5—C4—H4	110.7	C16B—C15B—C20B	119.96 (18)
O1—C5—C6	107.21 (16)	C16B—C15B—C14	119.31 (13)
O1—C5—C4	110.79 (16)	C20B—C15B—C14	119.65 (14)
C6—C5—C4	111.84 (17)	C17B—C16B—C15B	121.4 (2)
O1—C5—H5	109.0	C17B—C16B—H16B	119.3
C6—C5—H5	109.0	C15B—C16B—H16B	119.3
C4—C5—H5	109.0	C16B—C17B—C18B	117.7 (3)
O4—C6—C5	112.61 (17)	C16B—C17B—H17B	121.1
O4—C6—H61	109.1	C18B—C17B—H17B	121.1
C5—C6—H61	109.1	C19B—C18B—C17B	121.6 (3)
O4—C6—H62	109.1	C19B—C18B—H18B	119.2
C5—C6—H62	109.1	C17B—C18B—H18B	119.2
H61—C6—H62	107.8	C18B—C19B—C20B	119.7 (3)
O5—C7—N1	127.1 (2)	C18B—C19B—H19B	120.1
O5—C7—O2	122.2 (2)	C20B—C19B—H19B	120.1
N1—C7—O2	110.73 (18)	C19B—C20B—C15B	119.3 (3)
C9A—C8A—C13A	123.2 (2)	C19B—C20B—H20B	120.4
C9A—C8A—S1	123.05 (17)	C15B—C20B—H20B	120.4
C13A—C8A—S1	113.15 (17)	O4—C21—C22	109.66 (19)
C8A—C9A—C10A	120.3 (3)	O4—C21—H211	109.7
C8A—C9A—H9A	119.9	C22—C21—H211	109.7
C10A—C9A—H9A	119.9	O4—C21—H212	109.7
C11A—C10A—C9A	115.3 (3)	C22—C21—H212	109.7
C11A—C10A—H10A	122.4	H211—C21—H212	108.2
C9A—C10A—H10A	122.4	C27—C22—C23	118.9 (2)
C12A—C11A—C10A	125.3 (3)	C27—C22—C21	121.8 (2)
C12A—C11A—H11A	117.4	C23—C22—C21	119.3 (2)
C10A—C11A—H11A	117.4	C24—C23—C22	121.0 (2)
C11A—C12A—C13A	118.6 (3)	C24—C23—H23	119.5
C11A—C12A—H12A	120.7	C22—C23—H23	119.5
C13A—C12A—H12A	120.7	C25—C24—C23	119.6 (2)
C12A—C13A—C8A	117.0 (3)	C25—C24—H24	120.2
C12A—C13A—H13A	121.5	C23—C24—H24	120.2
C8A—C13A—H13A	121.5	C24—C25—C26	120.5 (3)
C9B—C8B—C13B	110.8 (3)	C24—C25—H25	119.8
C9B—C8B—S1	120.9 (2)	C26—C25—H25	119.8
C13B—C8B—S1	127.1 (2)	C25—C26—C27	119.1 (3)
C8B—C9B—C10B	119.3 (3)	C25—C26—H26	120.4
C8B—C9B—H9B	120.3	C27—C26—H26	120.4
C10B—C9B—H9B	120.3	C22—C27—C26	120.9 (2)
C11B—C10B—C9B	128.2 (4)	C22—C27—H27	119.5
C11B—C10B—H10B	115.9	C26—C27—H27	119.5

O1—C1—C2—C3	63.0 (2)	C9A—C8A—C13A—C12A	−6.4 (7)
C1—C2—C3—C4	−68.1 (2)	S1—C8A—C13A—C12A	−178.0 (4)
C2—C3—C4—C5	61.6 (2)	C1—S1—C8B—C9B	77.6 (3)
C3—C4—C5—O1	−55.9 (2)	C1—S1—C8B—C13B	−88.4 (4)
C4—C5—O1—C1	61.9 (2)	C13B—C8B—C9B—C10B	−17.1 (6)
C5—O1—C1—C2	−63.1 (2)	S1—C8B—C9B—C10B	174.8 (3)
C5—O1—C1—S1	176.16 (12)	C8B—C9B—C10B—C11B	8.0 (7)
C8A—S1—C1—O1	−80.49 (16)	C9B—C10B—C11B—C12B	6.1 (8)
C8B—S1—C1—O1	−82.40 (16)	C10B—C11B—C12B—C13B	−8.8 (7)
C8A—S1—C1—C2	164.18 (16)	C11B—C12B—C13B—C8B	−2.0 (8)
C8B—S1—C1—C2	162.27 (16)	C9B—C8B—C13B—C12B	15.3 (7)
C7—N1—C2—C3	−30.61 (19)	S1—C8B—C13B—C12B	−177.6 (4)
C14—N1—C2—C3	−178.55 (14)	C7—N1—C14—C15B	−88.23 (17)
C7—N1—C2—C1	−145.7 (2)	C2—N1—C14—C15B	56.42 (17)
C14—N1—C2—C1	66.3 (2)	C7—N1—C14—C15A	−88.61 (17)
O1—C1—C2—N1	173.76 (17)	C2—N1—C14—C15A	56.03 (17)
S1—C1—C2—N1	−68.9 (2)	N1—C14—C15A—C16A	−125.37 (8)
S1—C1—C2—C3	−179.65 (14)	N1—C14—C15A—C20A	46.43 (19)
C7—O2—C3—C4	−154.83 (18)	C20A—C15A—C16A—C17A	3.7 (2)
C7—O2—C3—C2	−31.33 (19)	C14—C15A—C16A—C17A	176.01 (17)
N1—C2—C3—O2	36.67 (17)	C15A—C16A—C17A—C18A	−4.1 (4)
C1—C2—C3—O2	163.95 (15)	C16A—C17A—C18A—C19A	3.4 (5)
N1—C2—C3—C4	164.59 (15)	C17A—C18A—C19A—C20A	−2.5 (5)
O2—C3—C4—O3	−62.1 (2)	C18A—C19A—C20A—C15A	2.4 (5)
C2—C3—C4—O3	178.25 (15)	C16A—C15A—C20A—C19A	−2.9 (4)
O2—C3—C4—C5	−178.73 (16)	C14—C15A—C20A—C19A	−174.7 (2)
C1—O1—C5—C6	−175.85 (16)	N1—C14—C15B—C16B	−150.3 (2)
O3—C4—C5—O1	−176.08 (15)	N1—C14—C15B—C20B	41.6 (2)
O3—C4—C5—C6	64.4 (2)	C20B—C15B—C16B—C17B	−5.1 (5)
C3—C4—C5—C6	−175.48 (17)	C14—C15B—C16B—C17B	−173.2 (3)
C21—O4—C6—C5	75.1 (2)	C15B—C16B—C17B—C18B	3.8 (6)
O1—C5—C6—O4	51.8 (2)	C16B—C17B—C18B—C19B	−3.1 (7)
C4—C5—C6—O4	173.44 (16)	C17B—C18B—C19B—C20B	3.7 (7)
C14—N1—C7—O5	−16.3 (3)	C18B—C19B—C20B—C15B	−4.8 (6)
C2—N1—C7—O5	−166.1 (2)	C16B—C15B—C20B—C19B	5.5 (5)
C14—N1—C7—O2	162.90 (14)	C14—C15B—C20B—C19B	173.5 (3)
C2—N1—C7—O2	13.1 (2)	C6—O4—C21—C22	−172.10 (18)
C3—O2—C7—O5	−168.81 (19)	O4—C21—C22—C27	−1.1 (3)
C3—O2—C7—N1	12.0 (2)	O4—C21—C22—C23	178.6 (2)
C1—S1—C8A—C9A	51.4 (3)	C27—C22—C23—C24	0.0 (4)
C1—S1—C8A—C13A	−136.9 (3)	C21—C22—C23—C24	−179.7 (2)
C13A—C8A—C9A—C10A	7.4 (6)	C22—C23—C24—C25	−1.4 (4)
S1—C8A—C9A—C10A	178.2 (3)	C23—C24—C25—C26	1.4 (5)
C8A—C9A—C10A—C11A	−4.0 (6)	C24—C25—C26—C27	0.0 (5)
C9A—C10A—C11A—C12A	0.1 (7)	C23—C22—C27—C26	1.5 (4)
C10A—C11A—C12A—C13A	0.8 (8)	C21—C22—C27—C26	−178.8 (3)
C11A—C12A—C13A—C8A	2.2 (8)	C25—C26—C27—C22	−1.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5ⁱ	0.84	1.98	2.774 (2)	158

Symmetry code: (i) −x, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₇NO₅S
M_r	477.56
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	90
a, b, c (Å)	13.8166 (7), 5.7008 (3), 15.0425 (9)
β (°)	91.494 (4)
V (Å³)	1184.43 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.08 × 0.07

Data collection
Diffractometer	Rigaku AFC8 diffractometer with Saturn70 CCD
Absorption correction	Multi-scan (MULABS; Blessing, 1995)
T_min, T_max	0.959, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	7074, 4965, 3970
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.167, 1.03
No. of reflections	4965
No. of parameters	353
No. of restraints	31
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34
Absolute structure	Flack (1983), 1983 Friedel pairs
Absolute structure parameter	0.05 (11)

Computer programs: CrystalClear SM (Rigaku/MSC, 2005), HKL-2000 (Otwinowski & Minor, 1997), HKL-2000, SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5ⁱ	0.84	1.98	2.774 (2)	158.0

Symmetry code: (i) −x, y+1/2, −z+1.

Acknowledgements

SM acknowledges an Incentive Research Grant from RIKEN and Grants-in Aid for Scientific Research for Scientific Research (C) from the Japan Society for the Promotion of Science (grant No. 19590032).

References

Benakli, K., Zha, C. & Kerns, R. J. (2001). J. Am. Chem. Soc. 123, 9461–9462. Web of Science CrossRef PubMed CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Boysen, M., Gemma, E., Lahmann, M. & Oscarson, S. (2005). Chem. Commun. pp. 3044–3046. Web of Science CrossRef Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cremer, D. & Pople, A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Crich, D. & Vinod, A. U. (2005). J. Org. Chem. 70, 1291–1296. Web of Science CrossRef PubMed CAS 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
Geng, Y., Zhang, L.-H. & Ye, X.-S. (2008). Tetrahedron, 64, 4949–4958. Web of Science CrossRef CAS Google Scholar
Manabe, S., Ishii, K. & Ito, Y. (2006). J. Am. Chem. Soc. 128, 10666–10667. Web of Science CrossRef PubMed CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rigaku/MSC (2005). CrystalClear SM. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Satoh, H., Hutter, J., Luthi, H.-P., Manabe, S., Ishii, K. & Ito, Y. (2008). In preparation. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

Phenyl 2-amino-N,6-O-di­benzyl-2,3-N,O-carbonyl-2-de­­oxy-1-thio-β-D-gluco­pyran­oside

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside