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The crystal structure of the title compound, C22H24N2O10S, has been determined by X-ray diffraction. The molecule contains a sugar ring and a planar substituted heterocyclic ring linked, unusually, by an S atom. The sugar ring is in the normal chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014734/hg6044sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014734/hg6044Isup2.hkl
Contains datablock I

CCDC reference: 248825

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.046
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT162_ALERT_4_C Missing or Zero su (esd) on y-coordinate for ... S PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C12
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 27.44 From the CIF: _reflns_number_total 4988 Count of symmetry unique reflns 2979 Completeness (_total/calc) 167.44% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2009 Fraction of Friedel pairs measured 0.674 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare, 1994); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1999); molecular graphics: ORTEPIII (Johnson, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

(I) top
Crystal data top
C22H24N2O10SF(000) = 532.00
Mr = 508.50Dx = 1.398 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ybCell parameters from 3903 reflections
a = 11.50 (2) Åθ = 3.1–27.5°
b = 7.35 (1) ŵ = 0.19 mm1
c = 14.30 (2) ÅT = 173 K
β = 92.42 (2)°Block, colorless
V = 1208 (3) Å30.35 × 0.20 × 0.15 mm
Z = 2
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
4441 reflections with F2 > 2σ(F2)
Detector resolution: 14.63 pixels mm-1Rint = 0.021
ω scansθmax = 27.4°
Absorption correction: multi-scan
(Jacobson, 1998)
h = 1414
Tmin = 0.897, Tmax = 0.972k = 79
9357 measured reflectionsl = 1812
4988 independent reflections
Refinement top
Refinement on F w = 1/[σ2(Fo) + 0.00063|Fo|2]
R[F2 > 2σ(F2)] = 0.036(Δ/σ)max = 0.003
wR(F2) = 0.046Δρmax = 0.22 e Å3
S = 1.06Δρmin = 0.18 e Å3
4971 reflectionsAbsolute structure: Flack (1983)
315 parametersAbsolute structure parameter: 0.028 (6)
H-atom parameters not refined
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.12808 (5)0.55800.80704 (4)0.0308 (1)
O10.2824 (1)0.3359 (2)0.73653 (9)0.0256 (4)
O20.3607 (1)0.0649 (3)0.60502 (9)0.0320 (4)
O30.5201 (1)0.0962 (3)0.5706 (1)0.0493 (5)
O40.4886 (1)0.0149 (2)0.81296 (9)0.0251 (4)
O50.4128 (1)0.2852 (2)0.7688 (1)0.0431 (5)
O60.2964 (1)0.0413 (2)0.94629 (9)0.0243 (4)
O70.4612 (1)0.0495 (2)1.0375 (1)0.0364 (4)
O80.2028 (1)0.3082 (2)0.98238 (9)0.0245 (4)
O90.0112 (1)0.2438 (3)0.9617 (1)0.0380 (4)
O100.0380 (1)0.2569 (2)0.72297 (10)0.0267 (4)
N10.0947 (2)0.4530 (3)0.7688 (1)0.0386 (6)
N20.1523 (2)0.3070 (3)0.7223 (1)0.0383 (6)
C10.2479 (2)0.4014 (3)0.8249 (1)0.0240 (5)
C20.2256 (2)0.2418 (3)0.8902 (1)0.0220 (5)
C30.3332 (2)0.1215 (3)0.8995 (1)0.0213 (5)
C40.3764 (2)0.0733 (3)0.8026 (1)0.0214 (5)
C50.3925 (2)0.2444 (3)0.7447 (1)0.0242 (5)
C60.4331 (2)0.2049 (3)0.6476 (1)0.0313 (6)
C70.4152 (2)0.0831 (3)0.5713 (1)0.0346 (6)
C80.3300 (2)0.2229 (4)0.5379 (2)0.0554 (9)
C90.4959 (2)0.1946 (3)0.7917 (1)0.0273 (5)
C100.6192 (2)0.2570 (4)0.8016 (2)0.0379 (6)
C110.3665 (2)0.1102 (3)1.0165 (1)0.0240 (5)
C120.3083 (2)0.2669 (3)1.0611 (2)0.0335 (6)
C130.0899 (2)0.2997 (3)1.0107 (1)0.0263 (5)
C140.0830 (2)0.3658 (3)1.1091 (1)0.0306 (6)
C150.0147 (2)0.4171 (3)0.7665 (1)0.0282 (5)
C160.0718 (2)0.1952 (3)0.6979 (1)0.0266 (5)
C170.0828 (2)0.0217 (3)0.6496 (1)0.0253 (5)
C180.1935 (2)0.0379 (4)0.6192 (1)0.0329 (6)
C190.2052 (2)0.2001 (4)0.5718 (2)0.0422 (7)
C200.1091 (2)0.3055 (4)0.5551 (2)0.0441 (7)
C210.0008 (2)0.2482 (4)0.5862 (2)0.0400 (7)
C220.0144 (2)0.0844 (3)0.6334 (1)0.0322 (6)
H10.31280.46980.85240.0288*
H20.15980.17130.86590.0264*
H30.39410.18210.93660.0256*
H40.32120.00720.77050.0258*
H50.44870.32300.77700.0290*
H60.51340.16400.65160.0375*
H70.42740.31460.60990.0375*
H80.28360.26130.58950.0662*
H90.27940.17190.48870.0662*
H100.37120.32680.51380.0662*
H110.62330.38540.78650.0454*
H120.66620.18830.75930.0454*
H130.64820.23790.86550.0454*
H140.23570.22671.08640.0401*
H150.29250.36101.01470.0401*
H160.35880.31511.11120.0401*
H170.13230.29091.15020.0367*
H180.10920.49111.11290.0367*
H190.00320.35841.12810.0367*
H200.26160.03460.63140.0396*
H210.28190.24080.54980.0505*
H220.11820.41970.52160.0526*
H230.06830.32300.57500.0480*
H240.09130.04410.65480.0386*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0310 (3)0.0212 (3)0.0399 (3)0.0022 (2)0.0027 (2)0.0015 (2)
O10.0269 (7)0.0265 (8)0.0234 (7)0.0022 (6)0.0011 (5)0.0012 (6)
O20.0279 (7)0.0428 (9)0.0253 (7)0.0070 (7)0.0009 (5)0.0058 (7)
O30.0261 (8)0.057 (1)0.066 (1)0.0055 (8)0.0084 (8)0.0167 (9)
O40.0186 (7)0.0261 (8)0.0306 (7)0.0012 (6)0.0000 (5)0.0039 (6)
O50.0372 (9)0.0242 (9)0.067 (1)0.0066 (7)0.0029 (8)0.0003 (8)
O60.0232 (7)0.0252 (8)0.0244 (7)0.0041 (6)0.0011 (5)0.0069 (6)
O70.0273 (8)0.0363 (10)0.0447 (9)0.0013 (7)0.0099 (6)0.0090 (7)
O80.0206 (7)0.0302 (8)0.0230 (7)0.0045 (6)0.0028 (5)0.0034 (6)
O90.0244 (7)0.047 (1)0.0425 (9)0.0080 (7)0.0032 (6)0.0057 (8)
O100.0218 (7)0.0286 (8)0.0295 (7)0.0010 (6)0.0015 (5)0.0013 (6)
N10.0292 (10)0.036 (1)0.050 (1)0.0041 (9)0.0002 (8)0.0073 (9)
N20.0263 (9)0.040 (1)0.049 (1)0.0022 (9)0.0013 (8)0.0035 (9)
C10.0237 (10)0.023 (1)0.0250 (9)0.0027 (8)0.0007 (7)0.0004 (8)
C20.0206 (9)0.024 (1)0.0215 (9)0.0017 (8)0.0003 (7)0.0030 (8)
C30.0219 (9)0.021 (1)0.0210 (9)0.0040 (7)0.0022 (7)0.0030 (7)
C40.0189 (8)0.0206 (10)0.0246 (9)0.0023 (8)0.0001 (7)0.0023 (8)
C50.0214 (9)0.027 (1)0.0241 (9)0.0037 (8)0.0006 (7)0.0007 (8)
C60.032 (1)0.036 (1)0.027 (1)0.0005 (10)0.0057 (8)0.0024 (9)
C70.032 (1)0.046 (2)0.026 (1)0.008 (1)0.0054 (8)0.0071 (9)
C80.032 (1)0.070 (2)0.064 (2)0.005 (1)0.002 (1)0.038 (2)
C90.029 (1)0.024 (1)0.030 (1)0.0012 (9)0.0056 (8)0.0047 (8)
C100.031 (1)0.035 (1)0.049 (1)0.0072 (10)0.0072 (10)0.006 (1)
C110.026 (1)0.022 (1)0.0233 (9)0.0059 (8)0.0007 (7)0.0004 (7)
C120.035 (1)0.031 (1)0.034 (1)0.0007 (10)0.0008 (9)0.0119 (9)
C130.0247 (10)0.022 (1)0.032 (1)0.0016 (8)0.0058 (8)0.0037 (8)
C140.035 (1)0.027 (1)0.030 (1)0.0003 (9)0.0097 (9)0.0042 (9)
C150.030 (1)0.025 (1)0.029 (1)0.0042 (9)0.0008 (8)0.0007 (8)
C160.0196 (9)0.036 (1)0.0241 (9)0.0019 (9)0.0029 (7)0.0048 (8)
C170.0233 (9)0.034 (1)0.0188 (8)0.0016 (8)0.0006 (7)0.0041 (8)
C180.024 (1)0.044 (1)0.031 (1)0.0001 (10)0.0025 (8)0.001 (1)
C190.032 (1)0.053 (2)0.041 (1)0.009 (1)0.0048 (10)0.008 (1)
C200.043 (1)0.051 (2)0.039 (1)0.008 (1)0.006 (1)0.018 (1)
C210.032 (1)0.042 (1)0.047 (1)0.000 (1)0.0099 (10)0.009 (1)
C220.0230 (10)0.041 (1)0.033 (1)0.0049 (9)0.0026 (8)0.0013 (9)
Geometric parameters (Å, º) top
S—C11.805 (4)C17—C181.398 (4)
S—C151.745 (4)C17—C221.390 (4)
O1—C11.424 (3)C18—C191.375 (5)
O1—C51.434 (4)C19—C201.379 (4)
O2—C61.442 (4)C20—C211.387 (4)
O2—C71.354 (4)C21—C221.386 (4)
O3—C71.211 (3)C1—H10.9694
O4—C41.446 (4)C2—H20.9694
O4—C91.359 (4)C3—H30.9690
O5—C91.199 (3)C4—H40.9691
O6—C31.443 (4)C5—H50.9693
O6—C111.359 (3)C6—H60.9705
O7—C111.203 (3)C6—H70.9706
O8—C21.440 (3)C8—H80.9706
O8—C131.378 (3)C8—H90.9693
O9—C131.194 (3)C8—H100.9697
O10—C151.364 (3)C10—H110.9697
O10—C161.375 (3)C10—H120.9699
N1—N21.413 (4)C10—H130.9696
N1—C151.287 (4)C12—H140.9699
N2—C161.297 (4)C12—H150.9703
C1—C21.528 (4)C12—H160.9700
C2—C31.522 (4)C14—H170.9705
C3—C41.533 (4)C14—H180.9698
C4—C51.521 (4)C14—H190.9695
C5—C61.512 (3)C18—H200.9692
C7—C81.485 (4)C19—H210.9711
C9—C101.491 (4)C20—H220.9699
C11—C121.489 (4)C21—H230.9700
C13—C141.494 (3)C22—H240.9698
C16—C171.453 (4)
S···O83.196 (6)C11···O43.358 (6)
S···O93.505 (6)C12···O4x3.416 (7)
S···C133.520 (6)C13···S3.520 (6)
S···C14i3.563 (7)C14···Svi3.563 (7)
S···H19i2.8518C14···O9i3.135 (6)
O1···O22.908 (6)C15···O93.070 (6)
O1···O5ii3.187 (6)C15···C21ii3.562 (7)
O1···O102.869 (5)C18···O3xii3.365 (6)
O2···O12.908 (6)C18···C8vii3.546 (7)
O3···C18iii3.365 (6)C19···O3xii3.249 (6)
O3···C19iii3.249 (6)C20···C22xi3.592 (7)
O3···C93.267 (6)C21···C15v3.562 (7)
O4···C12iv3.416 (7)C22···C20vii3.592 (7)
O4···O62.986 (5)C4···H13.0950
O4···C113.358 (6)C8···H20xi3.0816
O5···O1v3.187 (6)C10···H17x2.9325
O5···C1v3.110 (6)C12···H18v3.0163
O5···C73.192 (6)C15···H22.8051
O6···O42.986 (5)C18···H12xii2.8481
O6···O82.841 (5)C22···H22vii2.8331
O7···C10iv3.309 (7)H1···O5ii2.4719
O8···S3.196 (6)H1···C43.0950
O8···O62.841 (5)H1···H32.5885
O9···C153.070 (6)H1···H52.2162
O9···C14vi3.135 (6)H2···O92.2975
O9···S3.505 (6)H2···O102.5087
O10···O12.869 (5)H2···C152.8051
O10···C23.154 (6)H3···O72.3411
O10···N22.219 (5)H3···H12.5885
O2···H42.4855H3···O7iv2.5973
O2···H21vii2.7555H4···O22.4855
O3···H10viii2.6585H4···O52.2995
O3···H21iii2.5416H5···O5ii2.9108
O3···H20iii2.7925H5···H12.2162
O3···H62.2389H6···O32.2389
O3···H7ix2.7547H6···O42.6815
O4···H62.6815H7···O3viii2.7547
O4···H16iv2.5003H8···O52.9139
O5···H1v2.4719H8···H232.5171
O5···H5v2.9108H10···O3ix2.6585
O5···H82.9139H10···H20xi2.5916
O5···H42.2995H12···C18iii2.8481
O7···H3x2.5973H13···O8x2.7328
O7···H32.3411H13···H17x2.5524
O8···H15ii2.6738H14···H18v2.5707
O8···H13iv2.7328H14···O9vi2.9012
O9···H22.2975H14···N2vi2.9472
O9···H14i2.9012H15···O8v2.6738
O9···H18vi2.5259H16···O4x2.5003
O10···H22.5087H17···N1vi2.7819
O10···H242.5042H17···C10iv2.9325
N1···O102.218 (5)H17···H13iv2.5524
N2···O102.219 (5)H18···C12ii3.0163
N1···H17i2.7819H18···H14ii2.5707
N2···H202.6721H18···O9i2.5259
N2···H14i2.9472H19···Svi2.8518
C1···O5ii3.110 (6)H20···O3xii2.7925
C2···O103.154 (6)H20···N22.6721
C4···C73.548 (7)H20···C8vii3.0816
C7···C93.350 (6)H20···H10vii2.5916
C7···O53.192 (6)H21···O3xii2.5416
C7···C43.548 (7)H21···O2xi2.7555
C8···C18xi3.546 (7)H22···C22xi2.8331
C9···C73.350 (6)H23···H82.5171
C9···O33.267 (6)H24···O102.5042
C10···O7x3.309 (7)
C1—S—C15102.93 (10)C2—C1—H1107.25
C1—O1—C5111.37 (13)O8—C2—H2109.86
C6—O2—C7117.12 (15)C1—C2—H2109.88
C4—O4—C9118.44 (16)C3—C2—H2109.89
C3—O6—C11118.37 (15)O6—C3—H3110.28
C2—O8—C13117.65 (14)C2—C3—H3110.30
C15—O10—C16102.00 (15)C4—C3—H3110.29
N2—N1—C15105.76 (19)O4—C4—H4109.79
N1—N2—C16106.4 (2)C3—C4—H4109.78
S—C1—O1109.24 (12)C5—C4—H4109.83
S—C1—C2115.42 (16)O1—C5—H5109.14
O1—C1—C2110.06 (17)C4—C5—H5109.11
O8—C2—C1109.94 (16)C6—C5—H5109.06
O8—C2—C3107.20 (13)O2—C6—H6109.56
C1—C2—C3110.04 (18)O2—C6—H7109.51
O6—C3—C2105.60 (17)C5—C6—H6109.60
O6—C3—C4109.88 (17)C5—C6—H7109.54
C2—C3—C4110.40 (14)H6—C6—H7109.38
O4—C4—C3109.44 (14)C7—C8—H8109.46
O4—C4—C5107.33 (17)C7—C8—H9109.49
C3—C4—C5110.64 (17)C7—C8—H10109.49
O1—C5—C4107.74 (17)H8—C8—H9109.38
O1—C5—C6108.73 (15)H8—C8—H10109.50
C4—C5—C6112.99 (17)H9—C8—H10109.51
O2—C6—C5109.25 (17)C9—C10—H11109.46
O2—C7—O3122.9 (2)C9—C10—H12109.47
O2—C7—C8111.19 (19)C9—C10—H13109.44
O3—C7—C8125.9 (2)H11—C10—H12109.52
O4—C9—O5123.0 (2)H11—C10—H13109.43
O4—C9—C10110.19 (19)H12—C10—H13109.50
O5—C9—C10126.8 (2)C11—C12—H14109.49
O6—C11—O7123.28 (18)C11—C12—H15109.45
O6—C11—C12109.96 (19)C11—C12—H16109.45
O7—C11—C12126.75 (19)H14—C12—H15109.45
O8—C13—O9122.93 (15)H14—C12—H16109.49
O8—C13—C14110.51 (17)H15—C12—H16109.49
O9—C13—C14126.6 (2)C13—C14—H17109.45
S—C15—O10120.37 (16)C13—C14—H18109.44
S—C15—N1125.96 (17)C13—C14—H19109.53
O10—C15—N1113.56 (19)H17—C14—H18109.43
O10—C16—N2112.28 (19)H17—C14—H19109.52
O10—C16—C17118.29 (19)H18—C14—H19109.46
N2—C16—C17129.4 (2)C17—C18—H20120.25
C16—C17—C18118.9 (2)C19—C18—H20120.16
C16—C17—C22121.1 (2)C18—C19—H21119.69
C18—C17—C22120.0 (2)C20—C19—H21119.64
C17—C18—C19119.6 (2)C19—C20—H22120.08
C18—C19—C20120.7 (2)C21—C20—H22119.92
C19—C20—C21120.0 (3)C20—C21—H23119.97
C20—C21—C22120.2 (2)C22—C21—H23119.88
C17—C22—C21119.6 (2)C17—C22—H24120.33
S—C1—H1107.26C21—C22—H24120.11
O1—C1—H1107.26
S—C1—O1—C5166.9 (1)N2—C16—C17—C183.4 (3)
S—C1—C2—O861.8 (2)N2—C16—C17—C22176.8 (2)
S—C1—C2—C3179.7 (1)C1—O1—C5—C466.0 (2)
S—C15—O10—C16176.6 (1)C1—O1—C5—C6171.1 (2)
S—C15—N1—N2175.6 (2)C1—C2—O8—C13106.8 (2)
O1—C1—S—C1568.6 (1)C1—C2—C3—C450.2 (2)
O1—C1—C2—O8174.0 (1)C2—O8—C13—C14177.4 (2)
O1—C1—C2—C356.1 (2)C2—C1—S—C1556.1 (2)
O1—C5—C4—O4178.2 (1)C2—C1—O1—C565.3 (2)
O1—C5—C4—C358.8 (2)C2—C3—O6—C11135.8 (2)
O1—C5—C6—O270.7 (2)C2—C3—C4—C552.4 (2)
O2—C6—C5—C449.0 (2)C3—O6—C11—C12174.8 (2)
O3—C7—O2—C64.5 (3)C3—C2—O8—C13133.5 (2)
O4—C4—C3—O673.2 (2)C3—C4—O4—C9110.7 (2)
O4—C4—C3—C2170.6 (2)C3—C4—C5—C6179.0 (2)
O4—C4—C5—C661.6 (2)C4—O4—C9—C10176.8 (2)
O5—C9—O4—C43.4 (3)C4—C3—O6—C11105.1 (2)
O6—C3—C2—O871.5 (2)C5—C4—O4—C9129.1 (2)
O6—C3—C2—C1168.9 (1)C5—C6—O2—C7126.2 (2)
O6—C3—C4—C5168.6 (1)C6—O2—C7—C8174.6 (2)
O7—C11—O6—C35.2 (3)C15—O10—C16—C17179.2 (2)
O8—C2—C3—C4169.7 (1)C15—N1—N2—C161.2 (2)
O9—C13—O8—C21.7 (3)C16—C17—C18—C19178.7 (2)
O10—C15—S—C125.0 (2)C16—C17—C22—C21179.3 (2)
O10—C15—N1—N20.6 (2)C17—C18—C19—C200.9 (4)
O10—C16—N2—N11.3 (2)C17—C22—C21—C200.3 (3)
O10—C16—C17—C18176.5 (2)C18—C17—C22—C210.5 (3)
O10—C16—C17—C223.3 (3)C18—C19—C20—C210.0 (4)
N1—N2—C16—C17178.8 (2)C19—C18—C17—C221.1 (3)
N1—C15—S—C1159.0 (2)C19—C20—C21—C220.6 (4)
N1—C15—O10—C160.1 (2)C19—C20—C21—C220.6 (4)
N2—C16—O10—C150.9 (2)
Symmetry codes: (i) x, y+1/2, z+2; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x+1, y+1/2, z+2; (v) x, y1, z; (vi) x, y1/2, z+2; (vii) x, y+1/2, z+1; (viii) x+1, y+1/2, z+1; (ix) x+1, y1/2, z+1; (x) x+1, y1/2, z+2; (xi) x, y1/2, z+1; (xii) x1, y, z.
 

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