1-(2,3,4,6-Tetra-O-acetyl-β-d-gluco­pyranos­yl)-3-thio­ureidothio­urea monohydrate

Sun, W.; Yao, J.; Bai, L.; Wang, X.

doi:10.1107/S1600536808043833

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o242

doi:10.1107/S1600536808043833

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1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-3-thioureidothiourea monohydrate

Weidong Sun,^a Jin Yao,^b Lifei Bai ^c and Xiaoming Wang ^d ^*

^aDepartment of Chemistry, Chifeng College, Chifeng 024001, People's Republic of China, ^bCollege of Chemistry, Nanjing University, Hankou Road, Nanjing,210093, People's Republic of China, ^cJiangsu Key Laboratory of Chinese Medicine Processing, Nanjing University of Chinese Medicine, Nanjing, 210029, People's Republic of China, and ^dState Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Hankou Road, Nanjing,210093, People's Republic of China
^*Correspondence e-mail: wangxm07@nju.edu.cn

(Received 15 December 2008; accepted 24 December 2008; online 8 January 2009)

In the title compound, C₁₆H₂₄N₄O₉S₂·H₂O, the hexopyranosyl ring adopts a chair conformation (⁴C₁), and the five substituents are in equatorial positions. In the crystal structure, extensive O—H⋯O, N—H⋯S and N—H⋯O hydrogen bonding leads to the formation of a three-dimensional network.

Related literature

For cycloaddition and nucleophilic addition, see: Pearson et al. (2003 ); Reitz et al. (1989 ). For the crystal structure of glycosyl isothiosyanate, see: Jiang et al. (2003 ). For the crystal structures of glycosyl isothiosyanate methanol and ethanol derivatives, see: Zhang et al. (2001 ).

Experimental

Crystal data

C₁₆H₂₄N₄O₉S₂·H₂O
M_r = 498.53
Monoclinic, C 2
a = 22.286 (2) Å
b = 7.2005 (7) Å
c = 15.8772 (17) Å
β = 110.119 (2)°
V = 2392.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 (2) K
0.45 × 0.22 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
6322 measured reflections
3525 independent reflections
3021 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.141
S = 1.07
3525 reflections
289 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 1229 Friedel pairs
Flack parameter: −0.16 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H10⋯O5ⁱ	0.87	2.64	3.382 (11)	146
O1W—H20⋯O9ⁱⁱ	0.87	2.56	3.181 (9)	129
N1—H1A⋯S2ⁱⁱⁱ	0.86	2.62	3.400 (4)	151
N2—H2A⋯O3^iv	0.86	2.09	2.856 (5)	147
N3—H3A⋯O1W^v	0.86	2.13	2.973 (9)	167
N4—H4B⋯O1W^vi	0.86	2.43	3.244 (9)	159
N4—H4C⋯O1ⁱⁱⁱ	0.86	2.49	3.323 (5)	164
Symmetry codes: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x-1, y, z; (iii) -x+2, y, -z+1; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) x+1, y, z; (vi) x+1, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536808043833/su2088sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043833/su2088Isup2.hkl

checkCIF report

Comment top

Over the past decade, many organic chemists have been engaged in the synthesis of glycosyl isothiosyanates and its derivatives. These compound are versatile reagents in organic synthesis and easily undergo many important reactions, such as cycloaddition (Pearson et al., 2003) and nucleophilic addition (Reitz et al., 1989). Recently, the crystal structures of glycosyl isothiosyanate (Jiang et al., 2003) and the methanol and ethanol derivatives (Zhang et al., 2001) have been reported. However, other derivatives of glycosyl isothiosyanate are still rare. Here we report on the synthesis of a new thiosemicarbazide derivative of glycosyl isothiosyanate, 2,3,4,6-tetra-O-acetyl- β-D-glucopyranosyl dithiourea, (I).

The molecular structure of compound (I) is illustrated in Fig. 1. The hexopyranosyl ring adopts a chair conformation (⁴C₁), and the four substituents are in equatorial positions.

In the crystal extensive O—H···O, N—H···S and N—H···O hydrogen bonding (Table 1) leads to the formation of a three-dimensional network.

Related literature top

For cycloaddition and nucleophilic addition, see: Pearson et al. (2003); Reitz et al. (1989). For the crystal structure of glycosyl isothiosyanate, see: Jiang et al. (2003). For the crystal structures of glycosyl isothiosyanate methanol and ethanol derivatives, see: Zhang et al. (2001).

Experimental top

Compound (I) was prepared by refluxing together equimolar amounts of β-D-2,3,4,6-tetra-O- acetyl-glucopyranosyl isothiocyanate and thiosemicarbazide. After cooling to room temperature, water was added to the mixture and compound (I) was isolated as a white solid. Crystals, suitable for X-ray analysis, were grown from an ethyl acetate and acetonitrile (1:1 / v:v) solution by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecular structure of compound (I), showing the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level.

1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-3-thioureidothiourea monohydrate top

Crystal data top

C₁₆H₂₄N₄O₉S₂·H₂O	F(000) = 1048
M_r = 498.53	D_x = 1.384 Mg m⁻³
Monoclinic, C2	Melting point: not measured K
Hall symbol: C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 22.286 (2) Å	Cell parameters from 7141 reflections
b = 7.2005 (7) Å	θ = 1.4–27.7°
c = 15.8772 (17) Å	µ = 0.28 mm⁻¹
β = 110.119 (2)°	T = 293 K
V = 2392.3 (4) Å³	Block, colorless
Z = 4	0.45 × 0.22 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3021 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 25.0°, θ_min = 1.4°
ϕ scans, and ω scans	h = −25→26
6322 measured reflections	k = −8→8
3525 independent reflections	l = −18→11

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0808P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3525 reflections	Δρ_max = 0.42 e Å⁻³
289 parameters	Δρ_min = −0.27 e Å⁻³
7 restraints	Absolute structure: Flack (1983), 1229 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.16 (12)

Crystal data top

C₁₆H₂₄N₄O₉S₂·H₂O	V = 2392.3 (4) Å³
M_r = 498.53	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 22.286 (2) Å	µ = 0.28 mm⁻¹
b = 7.2005 (7) Å	T = 293 K
c = 15.8772 (17) Å	0.45 × 0.22 × 0.22 mm
β = 110.119 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3021 reflections with I > 2σ(I)
6322 measured reflections	R_int = 0.036
3525 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.141	Δρ_max = 0.42 e Å⁻³
S = 1.07	Δρ_min = −0.27 e Å⁻³
3525 reflections	Absolute structure: Flack (1983), 1229 Friedel pairs
289 parameters	Absolute structure parameter: −0.16 (12)
7 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 > 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
O1W	0.0457 (4)	0.2431 (10)	0.3624 (6)	0.193 (3)
H10	0.0696	0.2068	0.3324	0.232*
H20	0.0081	0.1989	0.3326	0.232*
S1	1.01347 (6)	0.9344 (2)	0.17559 (9)	0.0605 (4)
S2	1.09337 (7)	0.5527 (2)	0.56716 (9)	0.0720 (5)
O1	0.87014 (12)	0.9697 (4)	0.28332 (19)	0.0433 (7)
O2	0.79211 (13)	1.1140 (5)	0.37749 (19)	0.0493 (8)
O3	0.69458 (16)	1.2284 (7)	0.3502 (3)	0.0796 (12)
O4	0.69663 (12)	0.9277 (5)	0.18084 (19)	0.0467 (7)
O5	0.67103 (18)	0.7887 (8)	0.2901 (3)	0.0880 (14)
O6	0.73828 (13)	0.5785 (4)	0.14481 (18)	0.0455 (7)
O7	0.71021 (18)	0.5906 (6)	−0.0050 (2)	0.0732 (11)
O8	0.86480 (13)	0.5944 (4)	0.12682 (18)	0.0464 (7)
O9	0.9131 (2)	0.3601 (6)	0.2159 (3)	0.0902 (14)
N1	0.95480 (15)	0.7892 (5)	0.2819 (2)	0.0427 (9)
H1A	0.9581	0.7239	0.3287	0.051*
N2	1.06247 (16)	0.7629 (6)	0.3289 (2)	0.0490 (10)
H2A	1.0987	0.7961	0.3256	0.059*
N3	1.06233 (17)	0.6483 (6)	0.3986 (2)	0.0496 (10)
H3A	1.0510	0.5342	0.3874	0.060*
N4	1.0852 (2)	0.8905 (7)	0.4975 (3)	0.0695 (13)
H4B	1.0779	0.9645	0.4526	0.083*
H4C	1.0960	0.9345	0.5510	0.083*
C1	0.89174 (18)	0.8500 (6)	0.2278 (3)	0.0396 (10)
H1B	0.8940	0.9195	0.1759	0.047*
C2	0.84790 (19)	0.6840 (6)	0.1959 (3)	0.0387 (10)
H2B	0.8538	0.5977	0.2459	0.046*
C3	0.77758 (18)	0.7409 (6)	0.1562 (3)	0.0387 (10)
H3B	0.7693	0.8028	0.0983	0.046*
C4	0.76213 (18)	0.8694 (6)	0.2203 (3)	0.0396 (10)
H4A	0.7681	0.8044	0.2768	0.047*
C5	0.8067 (2)	1.0374 (6)	0.2378 (3)	0.0423 (10)
H5A	0.8048	1.0902	0.1800	0.051*
C6	0.7926 (2)	1.1884 (7)	0.2936 (3)	0.0487 (11)
H6A	0.8249	1.2848	0.3050	0.058*
H6B	0.7514	1.2436	0.2612	0.058*
C7	0.7401 (3)	1.1452 (8)	0.3977 (4)	0.0586 (13)
C8	0.7464 (4)	1.0653 (12)	0.4877 (5)	0.102 (2)
H8A	0.7080	1.0891	0.5004	0.153*
H8B	0.7820	1.1220	0.5331	0.153*
H8C	0.7532	0.9337	0.4872	0.153*
C9	0.6553 (2)	0.8752 (8)	0.2213 (4)	0.0534 (12)
C10	0.5887 (2)	0.9374 (11)	0.1689 (4)	0.0745 (16)
H10A	0.5601	0.8955	0.1984	0.112*
H10B	0.5758	0.8859	0.1096	0.112*
H10C	0.5874	1.0705	0.1653	0.112*
C11	0.7051 (2)	0.5239 (7)	0.0609 (3)	0.0499 (12)
C12	0.6616 (3)	0.3661 (9)	0.0615 (4)	0.0735 (17)
H12A	0.6389	0.3273	0.0011	0.110*
H12B	0.6316	0.4054	0.0892	0.110*
H12C	0.6864	0.2642	0.0948	0.110*
C13	0.8985 (2)	0.4365 (7)	0.1448 (3)	0.0495 (11)
C14	0.9150 (2)	0.3741 (8)	0.0673 (4)	0.0643 (14)
H14A	0.9387	0.2602	0.0819	0.096*
H14B	0.9405	0.4672	0.0523	0.096*
H14C	0.8765	0.3543	0.0170	0.096*
C15	1.00857 (19)	0.8254 (6)	0.2658 (3)	0.0418 (10)
C16	1.0796 (2)	0.7105 (7)	0.4844 (3)	0.0495 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.265 (7)	0.099 (4)	0.166 (5)	0.007 (5)	0.012 (5)	−0.014 (4)
S1	0.0520 (7)	0.0731 (9)	0.0629 (8)	0.0127 (7)	0.0280 (6)	0.0215 (7)
S2	0.0840 (10)	0.0872 (11)	0.0403 (7)	0.0242 (8)	0.0154 (6)	0.0036 (7)
O1	0.0333 (14)	0.0484 (18)	0.0460 (17)	−0.0008 (13)	0.0109 (13)	−0.0055 (14)
O2	0.0468 (17)	0.053 (2)	0.0451 (18)	0.0115 (15)	0.0115 (14)	−0.0022 (15)
O3	0.050 (2)	0.104 (3)	0.088 (3)	0.024 (2)	0.029 (2)	0.003 (3)
O4	0.0344 (14)	0.0564 (19)	0.0471 (17)	0.0005 (15)	0.0112 (13)	−0.0011 (16)
O5	0.062 (2)	0.121 (4)	0.089 (3)	−0.011 (2)	0.036 (2)	0.022 (3)
O6	0.0445 (16)	0.0522 (19)	0.0344 (15)	−0.0082 (15)	0.0066 (13)	−0.0036 (14)
O7	0.092 (3)	0.079 (3)	0.0369 (19)	−0.017 (2)	0.0069 (18)	−0.0039 (19)
O8	0.0526 (17)	0.0488 (18)	0.0352 (15)	0.0105 (16)	0.0118 (13)	−0.0008 (14)
O9	0.132 (4)	0.073 (3)	0.081 (3)	0.047 (3)	0.056 (3)	0.023 (2)
N1	0.0352 (18)	0.051 (2)	0.041 (2)	0.0027 (17)	0.0117 (15)	0.0089 (17)
N2	0.0342 (19)	0.069 (3)	0.044 (2)	0.0034 (18)	0.0148 (17)	0.008 (2)
N3	0.046 (2)	0.052 (2)	0.040 (2)	0.0041 (18)	0.0019 (17)	−0.0040 (18)
N4	0.079 (3)	0.073 (3)	0.051 (3)	−0.007 (2)	0.016 (2)	−0.015 (2)
C1	0.038 (2)	0.042 (2)	0.039 (2)	0.0045 (19)	0.0128 (18)	0.0030 (19)
C2	0.041 (2)	0.047 (2)	0.028 (2)	0.0074 (19)	0.0111 (18)	0.0022 (18)
C3	0.036 (2)	0.044 (2)	0.033 (2)	−0.001 (2)	0.0078 (17)	0.0021 (19)
C4	0.031 (2)	0.051 (3)	0.035 (2)	0.0046 (19)	0.0101 (17)	0.0036 (19)
C5	0.042 (2)	0.042 (2)	0.041 (2)	0.001 (2)	0.0108 (19)	0.000 (2)
C6	0.049 (3)	0.041 (3)	0.056 (3)	−0.004 (2)	0.017 (2)	−0.002 (2)
C7	0.059 (3)	0.057 (3)	0.065 (3)	0.003 (3)	0.028 (3)	−0.008 (3)
C8	0.145 (6)	0.096 (5)	0.087 (5)	0.033 (5)	0.068 (4)	0.017 (4)
C9	0.044 (3)	0.060 (3)	0.059 (3)	−0.012 (2)	0.021 (2)	−0.012 (3)
C10	0.041 (3)	0.103 (5)	0.080 (4)	−0.006 (3)	0.022 (3)	−0.016 (4)
C11	0.046 (3)	0.052 (3)	0.045 (3)	0.003 (2)	0.007 (2)	−0.009 (2)
C12	0.068 (3)	0.075 (4)	0.062 (3)	−0.022 (3)	0.003 (3)	−0.018 (3)
C13	0.054 (3)	0.046 (3)	0.047 (3)	0.006 (2)	0.016 (2)	0.006 (3)
C14	0.062 (3)	0.067 (4)	0.070 (3)	0.014 (3)	0.031 (3)	−0.008 (3)
C15	0.037 (2)	0.045 (3)	0.043 (2)	0.007 (2)	0.0136 (19)	−0.005 (2)
C16	0.034 (2)	0.066 (3)	0.045 (3)	0.009 (2)	0.010 (2)	−0.011 (2)

Geometric parameters (Å, º) top

O1W—H10	0.868 (10)	C1—C2	1.516 (6)
O1W—H20	0.867 (8)	C1—H1B	0.9800
S1—C15	1.669 (5)	C2—C3	1.530 (5)
S2—C16	1.684 (5)	C2—H2B	0.9800
O1—C1	1.430 (5)	C3—C4	1.501 (6)
O1—C5	1.434 (5)	C3—H3B	0.9800
O2—C7	1.324 (6)	C4—C5	1.528 (6)
O2—C6	1.439 (6)	C4—H4A	0.9800
O3—C7	1.196 (6)	C5—C6	1.503 (6)
O4—C9	1.345 (6)	C5—H5A	0.9800
O4—C4	1.439 (5)	C6—H6A	0.9700
O5—C9	1.200 (6)	C6—H6B	0.9700
O6—C11	1.342 (5)	C7—C8	1.501 (9)
O6—C3	1.435 (5)	C8—H8A	0.9600
O7—C11	1.192 (6)	C8—H8B	0.9600
O8—C13	1.338 (6)	C8—H8C	0.9600
O8—C2	1.430 (5)	C9—C10	1.500 (7)
O9—C13	1.195 (6)	C10—H10A	0.9600
N1—C15	1.335 (5)	C10—H10B	0.9600
N1—C1	1.440 (5)	C10—H10C	0.9600
N1—H1A	0.8600	C11—C12	1.496 (8)
N2—C15	1.349 (5)	C12—H12A	0.9600
N2—N3	1.382 (5)	C12—H12B	0.9600
N2—H2A	0.8600	C12—H12C	0.9600
N3—C16	1.358 (6)	C13—C14	1.471 (7)
N3—H3A	0.8600	C14—H14A	0.9600
N4—C16	1.312 (7)	C14—H14B	0.9600
N4—H4B	0.8600	C14—H14C	0.9600
N4—H4C	0.8600

H10—O1W—H20	104.6 (8)	O2—C6—C5	110.3 (4)
C1—O1—C5	112.1 (3)	O2—C6—H6A	109.6
C7—O2—C6	116.6 (4)	C5—C6—H6A	109.6
C9—O4—C4	117.9 (4)	O2—C6—H6B	109.6
C11—O6—C3	117.9 (3)	C5—C6—H6B	109.6
C13—O8—C2	119.8 (3)	H6A—C6—H6B	108.1
C15—N1—C1	125.6 (4)	O3—C7—O2	123.8 (5)
C15—N1—H1A	117.2	O3—C7—C8	124.9 (5)
C1—N1—H1A	117.2	O2—C7—C8	111.3 (5)
C15—N2—N3	123.2 (4)	C7—C8—H8A	109.5
C15—N2—H2A	118.4	C7—C8—H8B	109.5
N3—N2—H2A	118.4	H8A—C8—H8B	109.5
C16—N3—N2	121.9 (4)	C7—C8—H8C	109.5
C16—N3—H3A	119.0	H8A—C8—H8C	109.5
N2—N3—H3A	119.0	H8B—C8—H8C	109.5
C16—N4—H4B	120.0	O5—C9—O4	123.2 (5)
C16—N4—H4C	120.0	O5—C9—C10	125.6 (5)
H4B—N4—H4C	120.0	O4—C9—C10	111.2 (5)
O1—C1—N1	106.4 (3)	C9—C10—H10A	109.5
O1—C1—C2	111.5 (3)	C9—C10—H10B	109.5
N1—C1—C2	110.1 (4)	H10A—C10—H10B	109.5
O1—C1—H1B	109.6	C9—C10—H10C	109.5
N1—C1—H1B	109.6	H10A—C10—H10C	109.5
C2—C1—H1B	109.6	H10B—C10—H10C	109.5
O8—C2—C1	107.6 (3)	O7—C11—O6	124.5 (4)
O8—C2—C3	107.9 (3)	O7—C11—C12	124.8 (5)
C1—C2—C3	112.2 (3)	O6—C11—C12	110.7 (4)
O8—C2—H2B	109.7	C11—C12—H12A	109.5
C1—C2—H2B	109.7	C11—C12—H12B	109.5
C3—C2—H2B	109.7	H12A—C12—H12B	109.5
O6—C3—C4	108.4 (3)	C11—C12—H12C	109.5
O6—C3—C2	109.1 (3)	H12A—C12—H12C	109.5
C4—C3—C2	109.1 (3)	H12B—C12—H12C	109.5
O6—C3—H3B	110.1	O9—C13—O8	122.9 (4)
C4—C3—H3B	110.1	O9—C13—C14	125.8 (5)
C2—C3—H3B	110.1	O8—C13—C14	111.4 (4)
O4—C4—C3	108.7 (3)	C13—C14—H14A	109.5
O4—C4—C5	110.3 (3)	C13—C14—H14B	109.5
C3—C4—C5	109.0 (3)	H14A—C14—H14B	109.5
O4—C4—H4A	109.7	C13—C14—H14C	109.5
C3—C4—H4A	109.7	H14A—C14—H14C	109.5
C5—C4—H4A	109.7	H14B—C14—H14C	109.5
O1—C5—C6	108.5 (3)	N1—C15—N2	114.9 (4)
O1—C5—C4	106.8 (3)	N1—C15—S1	125.8 (3)
C6—C5—C4	115.2 (4)	N2—C15—S1	119.3 (3)
O1—C5—H5A	108.7	N4—C16—N3	117.6 (5)
C6—C5—H5A	108.7	N4—C16—S2	124.1 (4)
C4—C5—H5A	108.7	N3—C16—S2	118.2 (4)

C15—N2—N3—C16	−107.9 (5)	C1—O1—C5—C6	−169.4 (3)
C5—O1—C1—N1	−178.7 (3)	C1—O1—C5—C4	65.9 (4)
C5—O1—C1—C2	−58.6 (4)	O4—C4—C5—O1	175.5 (3)
C15—N1—C1—O1	−116.8 (4)	C3—C4—C5—O1	−65.3 (4)
C15—N1—C1—C2	122.3 (5)	O4—C4—C5—C6	54.9 (5)
C13—O8—C2—C1	103.9 (4)	C3—C4—C5—C6	174.1 (4)
C13—O8—C2—C3	−134.9 (4)	C7—O2—C6—C5	−125.6 (4)
O1—C1—C2—O8	168.0 (3)	O1—C5—C6—O2	−64.5 (4)
N1—C1—C2—O8	−74.2 (4)	C4—C5—C6—O2	55.1 (5)
O1—C1—C2—C3	49.5 (4)	C6—O2—C7—O3	0.8 (7)
N1—C1—C2—C3	167.3 (3)	C6—O2—C7—C8	−178.4 (5)
C11—O6—C3—C4	129.2 (4)	C4—O4—C9—O5	2.9 (7)
C11—O6—C3—C2	−112.1 (4)	C4—O4—C9—C10	−176.6 (4)
O8—C2—C3—O6	73.5 (4)	C3—O6—C11—O7	7.1 (7)
C1—C2—C3—O6	−168.1 (3)	C3—O6—C11—C12	−173.9 (4)
O8—C2—C3—C4	−168.2 (3)	C2—O8—C13—O9	3.6 (7)
C1—C2—C3—C4	−49.9 (4)	C2—O8—C13—C14	−175.8 (4)
C9—O4—C4—C3	115.1 (4)	C1—N1—C15—N2	176.3 (4)
C9—O4—C4—C5	−125.6 (4)	C1—N1—C15—S1	−5.0 (7)
O6—C3—C4—O4	−63.5 (4)	N3—N2—C15—N1	8.6 (6)
C2—C3—C4—O4	177.8 (3)	N3—N2—C15—S1	−170.2 (3)
O6—C3—C4—C5	176.4 (3)	N2—N3—C16—N4	12.4 (7)
C2—C3—C4—C5	57.7 (4)	N2—N3—C16—S2	−166.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H10···O5ⁱ	0.868 (10)	2.637 (4)	3.382 (11)	144.5 (5)
O1W—H20···O9ⁱⁱ	0.867 (8)	2.563 (4)	3.181 (9)	129.1 (5)
N1—H1A···S2ⁱⁱⁱ	0.86	2.62	3.400 (4)	151
N2—H2A···O3^iv	0.86	2.09	2.856 (5)	147
N3—H3A···O1W^v	0.86	2.13	2.973 (9)	167
N4—H4B···O1W^vi	0.86	2.43	3.244 (9)	159
N4—H4C···O1ⁱⁱⁱ	0.86	2.49	3.323 (5)	164

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₄N₄O₉S₂·H₂O
M_r	498.53
Crystal system, space group	Monoclinic, C2
Temperature (K)	293
a, b, c (Å)	22.286 (2), 7.2005 (7), 15.8772 (17)
β (°)	110.119 (2)
V (Å³)	2392.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.45 × 0.22 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6322, 3525, 3021
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.141, 1.07
No. of reflections	3525
No. of parameters	289
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.27
Absolute structure	Flack (1983), 1229 Friedel pairs
Absolute structure parameter	−0.16 (12)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
O1W—H10···O5ⁱ	0.868 (10)	2.637 (4)	3.382 (11)	144.5 (5)
O1W—H20···O9ⁱⁱ	0.867 (8)	2.563 (4)	3.181 (9)	129.1 (5)
N1—H1A···S2ⁱⁱⁱ	0.86	2.62	3.400 (4)	151
N2—H2A···O3^iv	0.86	2.09	2.856 (5)	147
N3—H3A···O1W^v	0.86	2.13	2.973 (9)	167
N4—H4B···O1W^vi	0.86	2.43	3.244 (9)	159
N4—H4C···O1ⁱⁱⁱ	0.86	2.49	3.323 (5)	164

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

Acknowledgements

The project was supported by the National Natural Science Foundation of China (No. 30701041) and the Scientific Research Project of Inner Mongolia Autonomous Region Colleges and Universities (No. NJZY08149).

References

Bruker (2007). SMART and SAINT. 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
Jiang, F. F., Wen, L. R., Li, X. M., Zhang, S. S. & Jiao, K. (2003). Chem. J. Chin. Univ. 24, 58–60. Google Scholar
Pearson, M. S. M., Robin, A., Bourgougnon, N., Meslin, J. C. & Deniaud, D. (2003). J. Org. Chem. 68, 8583–8587. Web of Science CrossRef PubMed CAS Google Scholar
Reitz, A. B., Tuman, R. W., Marchione, C. S., Jordan, A. D., Bowden, C. R. & Maryanoff, B. E. (1989). J. Med. Chem. 32, 2110–2116. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, S.-S., Wang, Z.-W., Li, M., Jiao, K., Razak, I. A., Shanmuga Sundara Raj, S. & Fun, H.-K. (2001). Acta Cryst. C57, 566–568. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 2| February 2009| Page o242

doi:10.1107/S1600536808043833

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

1-(2,3,4,6-Tetra-O-acetyl-β-D-gluco­pyranos­yl)-3-thio­ureido­thio­urea monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-3-thioureidothiourea monohydrate