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In the title compound, C23H29N3O10S, the hexa­pyran­osyl ring adopts a chair conformation with all the substituents in equatorial positions. The mol­ecules are linked by C—H...S interactions into ribbons parallel to the a axis and two additional intermolecular C—H...O interactions provide further stability in a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025589/sj6012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025589/sj6012Isup2.hkl
Contains datablock I

CCDC reference: 255911

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.072
  • wR factor = 0.216
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 43 Perc. PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.17 Sigma PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.69 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.54 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C19 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O10B PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C23 H29 N3 O10 S
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.43 From the CIF: _reflns_number_total 6318 Count of symmetry unique reflns 3565 Completeness (_total/calc) 177.22% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2753 Fraction of Friedel pairs measured 0.772 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

4-Methoxybenzaldehyde 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazone top
Crystal data top
C23H29N3O10SDx = 1.292 Mg m3
Mr = 539.55Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6318 reflections
a = 8.7678 (5) Åθ = 1.5–27.4°
b = 17.6042 (9) ŵ = 0.17 mm1
c = 17.9730 (9) ÅT = 293 K
V = 2774.1 (3) Å3Needle, yellow
Z = 40.24 × 0.14 × 0.13 mm
F(000) = 1136
Data collection top
Siemens SMART CCD area-detector
diffractometer
6318 independent reflections
Radiation source: fine-focus sealed tube2708 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
Detector resolution: 8.33 pixels mm-1θmax = 27.4°, θmin = 1.6°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2222
Tmin = 0.960, Tmax = 0.978l = 2323
35973 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.072 w = 1/[σ2(Fo2) + (0.1011P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.216(Δ/σ)max = 0.001
S = 0.98Δρmax = 0.23 e Å3
6318 reflectionsΔρmin = 0.20 e Å3
345 parametersExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0038 (12)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2757 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.14 (15)
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
xyzUiso*/UeqOcc. (<1)
S10.96370 (16)0.38143 (9)0.06817 (9)0.0923 (5)
O11.4731 (7)0.3133 (3)0.4414 (3)0.1487 (19)
O20.9360 (4)0.12949 (17)0.04639 (18)0.0749 (8)
O31.0695 (5)0.1727 (2)0.14322 (19)0.0918 (11)
O41.0681 (4)0.00243 (19)0.01965 (19)0.0823 (10)
O50.8284 (5)0.0297 (2)0.0493 (3)0.1244 (15)
O61.1528 (4)0.0244 (2)0.1703 (2)0.0945 (11)
O71.3856 (6)0.0244 (3)0.1546 (3)0.144 (2)
O81.1897 (4)0.21454 (18)0.09354 (17)0.0735 (9)
O91.2553 (5)0.2345 (2)0.2510 (2)0.1129 (14)
O10A1.422 (3)0.2141 (16)0.3329 (8)0.148 (10)0.47 (4)
O10B1.310 (4)0.1650 (16)0.3437 (8)0.197 (12)0.53 (4)
N11.1675 (5)0.3605 (2)0.1238 (3)0.0782 (11)
N21.0978 (5)0.3907 (2)0.0632 (3)0.0856 (12)
H2A1.07990.43880.06180.103*
N31.0968 (4)0.2719 (2)0.0134 (2)0.0744 (11)
H3A1.14350.25970.05370.089*
C11.2775 (6)0.3829 (3)0.2417 (3)0.0818 (14)
C21.3510 (6)0.4362 (4)0.2872 (4)0.0956 (17)
H2B1.35300.48690.27250.115*
C31.4205 (8)0.4156 (4)0.3530 (4)0.106 (2)
H3B1.47090.45170.38170.127*
C41.4143 (8)0.3408 (4)0.3759 (4)0.109 (2)
C51.3387 (9)0.2871 (4)0.3332 (4)0.122 (2)
H5A1.33140.23710.34950.146*
C61.2736 (7)0.3086 (4)0.2656 (4)0.0999 (18)
H6A1.22660.27210.23610.120*
C71.5499 (10)0.3682 (6)0.4889 (4)0.165 (3)
H7A1.58810.34310.53250.248*
H7B1.63320.39080.46220.248*
H7C1.47900.40710.50340.248*
C81.2051 (6)0.4082 (3)0.1744 (3)0.0861 (16)
H8A1.18540.45960.16750.103*
C91.0550 (6)0.3456 (3)0.0038 (3)0.0737 (13)
C101.0674 (6)0.2135 (3)0.0402 (3)0.0696 (12)
H10B0.96950.22250.06500.084*
C111.0664 (6)0.1368 (3)0.0011 (3)0.0755 (13)
H11A1.16000.13060.02810.091*
C121.0547 (6)0.0746 (3)0.0579 (3)0.0719 (12)
H12A0.95540.07740.08280.086*
C131.1799 (6)0.0812 (3)0.1148 (3)0.0807 (14)
H13A1.27970.07350.09140.097*
C141.1718 (6)0.1588 (3)0.1505 (3)0.0799 (14)
H14A1.07240.16520.17460.096*
C150.9591 (7)0.1400 (3)0.1208 (3)0.0816 (14)
C160.8346 (7)0.1080 (4)0.1637 (3)0.111 (2)
H16A0.85300.11620.21570.167*
H16B0.74080.13220.14970.167*
H16C0.82760.05450.15400.167*
C170.9455 (8)0.0438 (3)0.0185 (4)0.0976 (17)
C180.9758 (8)0.1110 (4)0.0278 (5)0.132 (3)
H18A0.88620.14230.02950.199*
H18B1.05880.13930.00690.199*
H18C1.00200.09510.07730.199*
C191.2627 (10)0.0268 (4)0.1840 (4)0.111 (2)
C201.2114 (10)0.0806 (4)0.2431 (5)0.152 (3)
H20A1.29060.11690.25280.228*
H20B1.12120.10660.22680.228*
H20C1.18930.05280.28780.228*
C211.2962 (7)0.1706 (4)0.2063 (3)0.0975 (17)
H21A1.30750.12580.23720.117*
H21B1.39220.18010.18120.117*
C221.3030 (16)0.2386 (7)0.3205 (5)0.149 (3)
C231.2555 (13)0.3067 (7)0.3606 (5)0.198 (5)
H23A1.26020.34970.32780.297*
H23B1.32220.31490.40220.297*
H23C1.15290.30030.37810.297*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0881 (9)0.0881 (9)0.1005 (10)0.0086 (8)0.0044 (8)0.0186 (8)
O10.179 (5)0.153 (4)0.114 (4)0.010 (4)0.031 (4)0.014 (4)
O20.0684 (19)0.072 (2)0.085 (2)0.0090 (16)0.0012 (18)0.0031 (17)
O30.094 (3)0.101 (3)0.080 (2)0.008 (2)0.008 (2)0.004 (2)
O40.073 (2)0.076 (2)0.098 (2)0.0035 (18)0.0134 (19)0.0062 (18)
O50.106 (3)0.085 (3)0.182 (4)0.018 (2)0.034 (3)0.025 (3)
O60.096 (3)0.094 (3)0.094 (3)0.013 (2)0.009 (2)0.017 (2)
O70.122 (4)0.125 (4)0.186 (5)0.031 (3)0.001 (4)0.043 (4)
O80.071 (2)0.081 (2)0.0687 (19)0.0057 (17)0.0032 (17)0.0036 (17)
O90.153 (4)0.108 (3)0.078 (3)0.010 (3)0.021 (3)0.006 (2)
O10A0.134 (14)0.206 (19)0.105 (8)0.018 (13)0.032 (9)0.021 (9)
O10B0.25 (3)0.21 (2)0.133 (9)0.028 (19)0.035 (11)0.033 (10)
N10.088 (3)0.062 (3)0.085 (3)0.000 (2)0.018 (3)0.000 (3)
N20.094 (3)0.061 (2)0.101 (3)0.001 (2)0.018 (3)0.001 (3)
N30.078 (3)0.074 (3)0.071 (2)0.006 (2)0.003 (2)0.009 (2)
C10.085 (3)0.073 (4)0.087 (4)0.003 (3)0.021 (3)0.014 (3)
C20.095 (4)0.093 (4)0.099 (5)0.000 (3)0.016 (4)0.027 (4)
C30.101 (4)0.112 (5)0.106 (5)0.006 (4)0.004 (4)0.034 (4)
C40.118 (5)0.106 (6)0.104 (5)0.005 (4)0.004 (4)0.017 (4)
C50.161 (6)0.085 (5)0.119 (6)0.000 (5)0.011 (5)0.004 (4)
C60.117 (5)0.086 (4)0.097 (4)0.008 (3)0.003 (4)0.006 (3)
C70.170 (7)0.192 (9)0.134 (6)0.010 (8)0.040 (6)0.042 (7)
C80.084 (3)0.064 (3)0.110 (5)0.002 (3)0.034 (4)0.015 (3)
C90.070 (3)0.076 (3)0.075 (3)0.000 (3)0.011 (3)0.015 (3)
C100.069 (3)0.065 (3)0.074 (3)0.004 (2)0.005 (3)0.004 (2)
C110.070 (3)0.075 (3)0.082 (3)0.001 (3)0.007 (3)0.001 (3)
C120.069 (3)0.068 (3)0.078 (3)0.001 (2)0.009 (3)0.011 (3)
C130.080 (3)0.079 (3)0.083 (3)0.005 (3)0.016 (3)0.017 (3)
C140.073 (3)0.085 (4)0.082 (3)0.002 (3)0.007 (3)0.003 (3)
C150.089 (4)0.076 (3)0.080 (4)0.002 (3)0.002 (3)0.010 (3)
C160.121 (5)0.108 (5)0.104 (4)0.024 (4)0.010 (4)0.009 (4)
C170.091 (4)0.081 (4)0.121 (5)0.002 (4)0.015 (4)0.015 (3)
C180.124 (5)0.109 (5)0.164 (6)0.010 (4)0.011 (5)0.045 (5)
C190.108 (5)0.109 (5)0.117 (5)0.005 (5)0.010 (4)0.017 (4)
C200.176 (7)0.119 (5)0.161 (7)0.007 (5)0.027 (6)0.062 (5)
C210.102 (4)0.091 (4)0.100 (4)0.003 (4)0.003 (4)0.002 (3)
C220.158 (10)0.200 (13)0.088 (6)0.025 (8)0.003 (6)0.001 (7)
C230.229 (11)0.261 (12)0.105 (6)0.048 (10)0.019 (6)0.071 (7)
Geometric parameters (Å, º) top
S1—C91.646 (5)C5—H5A0.9300
O1—C41.374 (8)C6—H6A0.9300
O1—C71.455 (9)C7—H7A0.9600
O2—C151.365 (6)C7—H7B0.9600
O2—C111.432 (6)C7—H7C0.9600
O3—C151.196 (6)C8—H8A0.9300
O4—C171.348 (7)C10—C111.523 (7)
O4—C121.449 (5)C10—H10B0.9800
O5—C171.192 (6)C11—C121.501 (6)
O6—C191.342 (8)C11—H11A0.9800
O6—C131.433 (6)C12—C131.505 (7)
O7—C191.200 (8)C12—H12A0.9800
O8—C141.427 (6)C13—C141.510 (7)
O8—C101.438 (5)C13—H13A0.9800
O9—C221.320 (9)C14—C211.497 (8)
O9—C211.427 (7)C14—H14A0.9800
O10A—C221.154 (16)C15—C161.451 (8)
O10B—C221.36 (2)C16—H16A0.9600
N1—C81.281 (6)C16—H16B0.9600
N1—N21.358 (6)C16—H16C0.9600
N2—C91.383 (6)C17—C181.471 (9)
N2—H2A0.8600C18—H18A0.9600
N3—C91.359 (6)C18—H18B0.9600
N3—C101.432 (6)C18—H18C0.9600
N3—H3A0.8600C19—C201.492 (9)
C1—C61.377 (8)C20—H20A0.9600
C1—C21.402 (7)C20—H20B0.9600
C1—C81.437 (8)C20—H20C0.9600
C2—C31.379 (8)C21—H21A0.9700
C2—H2B0.9300C21—H21B0.9700
C3—C41.381 (9)C22—C231.459 (13)
C3—H3B0.9300C23—H23A0.9600
C4—C51.386 (9)C23—H23B0.9600
C5—C61.394 (9)C23—H23C0.9600
C4—O1—C7116.3 (6)C11—C12—H12A109.5
C15—O2—C11116.9 (4)C13—C12—H12A109.5
C17—O4—C12118.1 (4)O6—C13—C12107.3 (4)
C19—O6—C13118.5 (5)O6—C13—C14109.1 (4)
C14—O8—C10112.8 (3)C12—C13—C14108.9 (4)
C22—O9—C21119.8 (7)O6—C13—H13A110.5
C8—N1—N2115.3 (4)C12—C13—H13A110.5
N1—N2—C9121.1 (4)C14—C13—H13A110.5
N1—N2—H2A119.5O8—C14—C21107.7 (4)
C9—N2—H2A119.5O8—C14—C13108.2 (4)
C9—N3—C10123.5 (4)C21—C14—C13112.1 (5)
C9—N3—H3A118.3O8—C14—H14A109.6
C10—N3—H3A118.3C21—C14—H14A109.6
C6—C1—C2117.8 (6)C13—C14—H14A109.6
C6—C1—C8123.1 (5)O3—C15—O2121.1 (5)
C2—C1—C8119.1 (6)O3—C15—C16128.1 (5)
C3—C2—C1121.8 (6)O2—C15—C16110.9 (5)
C3—C2—H2B119.1C15—C16—H16A109.5
C1—C2—H2B119.1C15—C16—H16B109.5
C2—C3—C4119.2 (6)H16A—C16—H16B109.5
C2—C3—H3B120.4C15—C16—H16C109.5
C4—C3—H3B120.4H16A—C16—H16C109.5
O1—C4—C3125.2 (7)H16B—C16—H16C109.5
O1—C4—C5114.5 (7)O5—C17—O4123.6 (5)
C3—C4—C5120.3 (7)O5—C17—C18125.8 (6)
C4—C5—C6119.6 (7)O4—C17—C18110.5 (6)
C4—C5—H5A120.2C17—C18—H18A109.5
C6—C5—H5A120.2C17—C18—H18B109.5
C1—C6—C5121.3 (6)H18A—C18—H18B109.5
C1—C6—H6A119.4C17—C18—H18C109.5
C5—C6—H6A119.4H18A—C18—H18C109.5
O1—C7—H7A109.5H18B—C18—H18C109.5
O1—C7—H7B109.5O7—C19—O6122.7 (6)
H7A—C7—H7B109.5O7—C19—C20127.3 (8)
O1—C7—H7C109.5O6—C19—C20109.8 (7)
H7A—C7—H7C109.5C19—C20—H20A109.5
H7B—C7—H7C109.5C19—C20—H20B109.5
N1—C8—C1120.6 (5)H20A—C20—H20B109.5
N1—C8—H8A119.7C19—C20—H20C109.5
C1—C8—H8A119.7H20A—C20—H20C109.5
N3—C9—N2112.1 (4)H20B—C20—H20C109.5
N3—C9—S1126.6 (4)O9—C21—C14107.7 (5)
N2—C9—S1121.2 (4)O9—C21—H21A110.2
N3—C10—O8107.8 (4)C14—C21—H21A110.2
N3—C10—C11109.1 (4)O9—C21—H21B110.2
O8—C10—C11108.9 (4)C14—C21—H21B110.2
N3—C10—H10B110.3H21A—C21—H21B108.5
O8—C10—H10B110.3O10A—C22—O9116.7 (11)
C11—C10—H10B110.3O10A—C22—O10B62.9 (11)
O2—C11—C12106.6 (4)O9—C22—O10B104.6 (12)
O2—C11—C10111.0 (4)O10A—C22—C23118.1 (15)
C12—C11—C10109.5 (4)O9—C22—C23114.9 (9)
O2—C11—H11A109.9O10B—C22—C23130.1 (11)
C12—C11—H11A109.9C22—C23—H23A109.5
C10—C11—H11A109.9C22—C23—H23B109.5
O4—C12—C11108.1 (4)H23A—C23—H23B109.5
O4—C12—C13109.4 (4)C22—C23—H23C109.5
C11—C12—C13110.8 (4)H23A—C23—H23C109.5
O4—C12—H12A109.5H23B—C23—H23C109.5
C8—N1—N2—C9178.3 (4)C17—O4—C12—C11113.8 (5)
C6—C1—C2—C31.3 (8)C17—O4—C12—C13125.5 (5)
C8—C1—C2—C3179.0 (5)O2—C11—C12—O465.0 (4)
C1—C2—C3—C41.7 (9)C10—C11—C12—O4174.8 (4)
C7—O1—C4—C31.2 (10)O2—C11—C12—C13175.2 (4)
C7—O1—C4—C5178.4 (7)C10—C11—C12—C1355.0 (5)
C2—C3—C4—O1177.3 (6)C19—O6—C13—C12122.8 (5)
C2—C3—C4—C50.2 (10)C19—O6—C13—C14119.3 (6)
O1—C4—C5—C6179.7 (6)O4—C12—C13—O666.0 (5)
C3—C4—C5—C62.3 (11)C11—C12—C13—O6175.0 (4)
C2—C1—C6—C50.8 (8)O4—C12—C13—C14176.0 (4)
C8—C1—C6—C5176.7 (5)C11—C12—C13—C1456.9 (5)
C4—C5—C6—C12.7 (10)C10—O8—C14—C21174.3 (4)
N2—N1—C8—C1179.0 (4)C10—O8—C14—C1364.3 (5)
C6—C1—C8—N118.3 (8)O6—C13—C14—O8176.4 (4)
C2—C1—C8—N1164.2 (5)C12—C13—C14—O859.6 (5)
C10—N3—C9—N2179.4 (4)O6—C13—C14—C2164.9 (6)
C10—N3—C9—S10.7 (7)C12—C13—C14—C21178.3 (4)
N1—N2—C9—N32.6 (6)C11—O2—C15—O319.1 (7)
N1—N2—C9—S1177.3 (3)C11—O2—C15—C16161.7 (4)
C9—N3—C10—O885.4 (5)C12—O4—C17—O52.5 (9)
C9—N3—C10—C11156.5 (4)C12—O4—C17—C18175.3 (5)
C14—O8—C10—N3179.5 (4)C13—O6—C19—O74.1 (10)
C14—O8—C10—C1162.3 (5)C13—O6—C19—C20179.9 (5)
C15—O2—C11—C12139.2 (4)C22—O9—C21—C14150.8 (9)
C15—O2—C11—C10101.7 (5)O8—C14—C21—O977.0 (5)
N3—C10—C11—O269.4 (5)C13—C14—C21—O9164.0 (4)
O8—C10—C11—O2173.2 (3)C21—O9—C22—O10A35 (2)
N3—C10—C11—C12173.2 (4)C21—O9—C22—O10B31.8 (19)
O8—C10—C11—C1255.8 (5)C21—O9—C22—C23179.5 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···S1i0.982.773.713 (5)162
C16—H16B···S1ii0.962.853.682 (6)146
C18—H18C···O10Biii0.962.503.12 (3)123
C20—H20A···O3iv0.962.443.240 (9)140
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1/2, y+1/2, z; (iii) x+5/2, y, z1/2; (iv) x+5/2, y, z+1/2.
 

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