Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C13H20N4O8·2H2O, i.e. (I)·2H2O, shows no unusual features. The structure contains two mol­ecules of water of crystallization. The absolute configuration was not determined but was known from the starting materials.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011148/qa0376sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011148/qa0376Isup2.hkl
Contains datablock I

CCDC reference: 150752

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

N-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)- N-[β-D-glucopyranosyl]acetamide top
Crystal data top
C13H20N4O8·2H2ODx = 1.476 Mg m3
Mr = 396.36Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 2711 reflections
a = 7.0911 (1) Åθ = 3.0–30.4°
b = 12.2566 (2) ŵ = 0.13 mm1
c = 20.5272 (4) ÅT = 150 K
V = 1784.08 (5) Å3Lath, colourless
Z = 40.33 × 0.15 × 0.13 mm
F(000) = 840
Data collection top
KappaCCD
diffractometer
2711 independent reflections
Radiation source: fine-focus sealed X-ray tube2482 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scans with κ offsetsθmax = 29.0°, θmin = 3.0°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
h = 89
Tmin = 0.960, Tmax = 0.984k = 1617
12217 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.5011P]
where P = (Fo2 + 2Fc2)/3
2711 reflections(Δ/σ)max = 0.002
251 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.26 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2557 (3)0.83857 (13)0.36395 (8)0.0211 (3)
C20.4044 (3)0.83439 (15)0.40642 (9)0.0216 (4)
O20.4258 (3)0.90595 (13)0.44752 (7)0.0304 (4)
N30.5212 (3)0.74556 (13)0.40075 (8)0.0223 (4)
C310.6717 (4)0.7303 (2)0.44874 (11)0.0369 (6)
C40.5047 (3)0.66756 (15)0.35094 (9)0.0190 (4)
O40.6188 (2)0.59105 (12)0.34947 (7)0.0258 (3)
C50.3556 (3)0.68341 (14)0.30588 (8)0.0169 (3)
N50.3328 (2)0.60508 (12)0.25488 (7)0.0155 (3)
C510.2248 (3)0.51423 (15)0.26416 (9)0.0175 (4)
O510.2130 (2)0.44259 (11)0.22191 (7)0.0234 (3)
C520.1187 (3)0.50595 (16)0.32728 (9)0.0226 (4)
C60.2296 (3)0.76787 (14)0.31287 (9)0.0179 (4)
N60.0784 (3)0.78246 (14)0.27545 (8)0.0232 (4)
C1'0.4273 (3)0.62427 (14)0.19300 (9)0.0161 (3)
O1'0.3373 (2)0.71746 (11)0.16572 (6)0.0175 (3)
C2'0.6390 (3)0.64300 (15)0.20138 (9)0.0170 (4)
O2'0.9189 (2)0.69698 (12)0.14294 (7)0.0204 (3)
C3'0.7228 (3)0.67343 (15)0.13599 (9)0.0172 (4)
O3'0.7273 (2)0.54648 (11)0.22410 (7)0.0230 (3)
C4'0.6213 (3)0.77240 (15)0.10866 (8)0.0173 (4)
O4'0.6982 (2)0.80319 (13)0.04755 (7)0.0248 (3)
C5'0.4104 (3)0.74893 (15)0.10338 (8)0.0163 (3)
C51'0.3006 (3)0.84889 (16)0.08171 (9)0.0201 (4)
O5'0.1210 (2)0.82418 (13)0.05444 (7)0.0249 (3)
O60.0444 (2)0.49349 (12)0.10685 (7)0.0260 (3)
O70.7411 (3)0.01448 (14)0.00626 (8)0.0348 (4)
H10.17100.89010.36980.025*
H31A0.78930.76140.43190.055*
H31B0.68920.65220.45700.055*
H31C0.63730.76710.48940.055*
H52A0.05960.43390.33050.034*
H52B0.02100.56250.32880.034*
H52C0.20610.51610.36380.034*
H6A0.00070.83600.28390.028*
H6B0.05740.73860.24230.028*
H1'0.40660.56010.16380.019*
H2'0.66070.70350.23320.020*
H2'A0.98210.64080.13440.087 (14)*
H3'0.70710.61080.10520.021*
H3'A0.70890.54000.26430.028*
H4'0.63910.83440.13970.021*
H4'A0.66300.75880.01890.030*
H5'0.38950.68840.07150.020*
H51A0.28260.89760.11970.024*
H51B0.37610.88900.04900.024*
H5'A0.05470.79190.08230.030*
H6WA0.12090.47250.14220.031*
H6WB0.11360.49230.06380.031*
H7A0.85970.02190.00690.042*
H7B0.75940.04200.02350.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0232 (8)0.0193 (7)0.0209 (7)0.0039 (7)0.0006 (7)0.0039 (6)
C20.0244 (9)0.0197 (8)0.0208 (8)0.0019 (8)0.0010 (8)0.0008 (7)
O20.0352 (9)0.0271 (7)0.0289 (7)0.0002 (7)0.0051 (7)0.0111 (6)
N30.0252 (9)0.0214 (8)0.0203 (7)0.0020 (7)0.0047 (7)0.0025 (6)
C310.0389 (13)0.0378 (12)0.0341 (11)0.0092 (11)0.0177 (11)0.0049 (10)
C40.0208 (9)0.0186 (8)0.0176 (8)0.0011 (7)0.0006 (7)0.0012 (7)
O40.0284 (8)0.0253 (7)0.0238 (6)0.0098 (6)0.0036 (6)0.0007 (6)
C50.0187 (9)0.0159 (8)0.0160 (7)0.0005 (7)0.0001 (7)0.0002 (6)
N50.0164 (7)0.0139 (6)0.0162 (6)0.0010 (6)0.0011 (6)0.0003 (5)
C510.0159 (8)0.0185 (8)0.0181 (7)0.0009 (7)0.0013 (7)0.0044 (7)
O510.0279 (8)0.0192 (6)0.0230 (6)0.0077 (6)0.0009 (6)0.0009 (5)
C520.0224 (9)0.0229 (9)0.0224 (8)0.0015 (8)0.0038 (8)0.0038 (7)
C60.0191 (9)0.0177 (8)0.0170 (7)0.0006 (7)0.0018 (7)0.0007 (7)
N60.0227 (8)0.0225 (8)0.0243 (8)0.0078 (7)0.0038 (7)0.0061 (6)
C1'0.0157 (8)0.0156 (8)0.0169 (8)0.0003 (7)0.0013 (7)0.0008 (6)
O1'0.0152 (6)0.0200 (6)0.0171 (5)0.0022 (5)0.0019 (5)0.0042 (5)
C2'0.0148 (8)0.0167 (8)0.0194 (8)0.0017 (7)0.0013 (7)0.0003 (7)
O2'0.0124 (6)0.0232 (7)0.0257 (6)0.0001 (5)0.0012 (6)0.0003 (6)
C3'0.0142 (8)0.0185 (8)0.0188 (7)0.0016 (7)0.0004 (7)0.0010 (7)
O3'0.0227 (7)0.0229 (7)0.0233 (6)0.0072 (6)0.0026 (6)0.0061 (5)
C4'0.0167 (9)0.0192 (8)0.0160 (7)0.0024 (7)0.0022 (7)0.0007 (6)
O4'0.0208 (7)0.0328 (8)0.0207 (6)0.0043 (6)0.0042 (6)0.0066 (6)
C5'0.0162 (8)0.0179 (8)0.0149 (7)0.0019 (7)0.0008 (7)0.0010 (6)
C51'0.0170 (9)0.0193 (8)0.0240 (8)0.0010 (7)0.0009 (8)0.0040 (7)
O5'0.0163 (7)0.0283 (7)0.0301 (7)0.0013 (6)0.0031 (6)0.0064 (6)
O60.0236 (7)0.0284 (7)0.0261 (6)0.0002 (6)0.0010 (6)0.0010 (6)
O70.0333 (9)0.0391 (9)0.0319 (8)0.0070 (8)0.0033 (7)0.0075 (7)
Geometric parameters (Å, º) top
N1—C21.369 (3)C1'—C2'1.528 (3)
N1—C61.373 (2)C1'—H1'1.0000
N1—H10.8800O1'—C5'1.434 (2)
C2—O21.226 (2)C2'—O3'1.417 (2)
C2—N31.373 (3)C2'—C3'1.515 (3)
N3—C41.405 (2)C2'—H2'1.0000
N3—C311.464 (3)O2'—C3'1.428 (2)
C31—H31A0.9800O2'—H2'A0.8400
C31—H31B0.9800C3'—C4'1.518 (3)
C31—H31C0.9800C3'—H3'1.0000
C4—O41.239 (2)O3'—H3'A0.8400
C4—C51.418 (3)C4'—O4'1.419 (2)
C5—C61.375 (2)C4'—C5'1.527 (3)
C5—N51.430 (2)C4'—H4'1.0000
N5—C511.365 (2)O4'—H4'A0.8400
N5—C1'1.455 (2)C5'—C51'1.518 (3)
C51—O511.237 (2)C5'—H5'1.0000
C51—C521.502 (3)C51'—O5'1.423 (2)
C52—H52A0.9800C51'—H51A0.9900
C52—H52B0.9800C51'—H51B0.9900
C52—H52C0.9800O5'—H5'A0.8400
C6—N61.331 (3)O6—H6WA0.9419
N6—H6A0.8800O6—H6WB1.0109
N6—H6B0.8800O7—H7A0.8882
C1'—O1'1.423 (2)O7—H7B0.7883
C2—N1—C6124.52 (17)N5—C1'—C2'112.22 (15)
C2—N1—H1117.7O1'—C1'—H1'109.2
C6—N1—H1117.7N5—C1'—H1'109.2
O2—C2—N1120.46 (19)C2'—C1'—H1'109.2
O2—C2—N3123.41 (19)C1'—O1'—C5'113.89 (14)
N1—C2—N3116.11 (16)O3'—C2'—C3'108.89 (15)
C2—N3—C4123.45 (17)O3'—C2'—C1'110.21 (15)
C2—N3—C31118.93 (17)C3'—C2'—C1'108.82 (15)
C4—N3—C31117.62 (17)O3'—C2'—H2'109.6
N3—C31—H31A109.5C3'—C2'—H2'109.6
N3—C31—H31B109.5C1'—C2'—H2'109.6
H31A—C31—H31B109.5C3'—O2'—H2'A109.5
N3—C31—H31C109.5O2'—C3'—C2'110.09 (15)
H31A—C31—H31C109.5O2'—C3'—C4'109.71 (15)
H31B—C31—H31C109.5C2'—C3'—C4'109.77 (15)
O4—C4—N3118.57 (17)O2'—C3'—H3'109.1
O4—C4—C5125.08 (17)C2'—C3'—H3'109.1
N3—C4—C5116.34 (17)C4'—C3'—H3'109.1
C6—C5—C4121.30 (17)C2'—O3'—H3'A109.5
C6—C5—N5120.55 (16)O4'—C4'—C3'110.92 (15)
C4—C5—N5118.05 (16)O4'—C4'—C5'111.33 (15)
C51—N5—C5120.62 (15)C3'—C4'—C5'109.89 (15)
C51—N5—C1'120.79 (15)O4'—C4'—H4'108.2
C5—N5—C1'118.59 (14)C3'—C4'—H4'108.2
O51—C51—N5121.30 (17)C5'—C4'—H4'108.2
O51—C51—C52121.52 (18)C4'—O4'—H4'A109.5
N5—C51—C52117.18 (16)O1'—C5'—C51'107.06 (15)
C51—C52—H52A109.5O1'—C5'—C4'109.97 (15)
C51—C52—H52B109.5C51'—C5'—C4'111.78 (15)
H52A—C52—H52B109.5O1'—C5'—H5'109.3
C51—C52—H52C109.5C51'—C5'—H5'109.3
H52A—C52—H52C109.5C4'—C5'—H5'109.3
H52B—C52—H52C109.5O5'—C51'—C5'113.71 (16)
N6—C6—N1117.69 (17)O5'—C51'—H51A108.8
N6—C6—C5124.36 (17)C5'—C51'—H51A108.8
N1—C6—C5117.86 (17)O5'—C51'—H51B108.8
C6—N6—H6A120.0C5'—C51'—H51B108.8
C6—N6—H6B120.0H51A—C51'—H51B107.7
H6A—N6—H6B120.0C51'—O5'—H5'A109.5
O1'—C1'—N5105.46 (14)H6WA—O6—H6WB113.0
O1'—C1'—C2'111.36 (14)H7A—O7—H7B94.0
C6—N1—C2—O2173.96 (19)N5—C5—C6—N1178.06 (16)
C6—N1—C2—N37.5 (3)C51—N5—C1'—O1'112.87 (17)
O2—C2—N3—C4175.41 (19)C5—N5—C1'—O1'67.23 (19)
N1—C2—N3—C46.1 (3)C51—N5—C1'—C2'125.72 (17)
O2—C2—N3—C314.5 (3)C5—N5—C1'—C2'54.2 (2)
N1—C2—N3—C31173.97 (19)N5—C1'—O1'—C5'179.34 (14)
C2—N3—C4—O4178.96 (18)C2'—C1'—O1'—C5'58.68 (19)
C31—N3—C4—O41.0 (3)O1'—C1'—C2'—O3'175.74 (13)
C2—N3—C4—C51.2 (3)N5—C1'—C2'—O3'66.29 (19)
C31—N3—C4—C5178.92 (18)O1'—C1'—C2'—C3'56.40 (18)
O4—C4—C5—C6176.88 (19)N5—C1'—C2'—C3'174.37 (14)
N3—C4—C5—C63.0 (3)O3'—C2'—C3'—O2'62.83 (19)
O4—C4—C5—N50.6 (3)C1'—C2'—C3'—O2'177.00 (15)
N3—C4—C5—N5179.30 (16)O3'—C2'—C3'—C4'176.30 (14)
C6—C5—N5—C5188.2 (2)C1'—C2'—C3'—C4'56.13 (19)
C4—C5—N5—C5188.2 (2)O2'—C3'—C4'—O4'58.44 (19)
C6—C5—N5—C1'91.9 (2)C2'—C3'—C4'—O4'179.53 (15)
C4—C5—N5—C1'91.7 (2)O2'—C3'—C4'—C5'178.03 (14)
C5—N5—C51—O51175.57 (17)C2'—C3'—C4'—C5'56.94 (19)
C1'—N5—C51—O514.3 (3)C1'—O1'—C5'—C51'179.70 (14)
C5—N5—C51—C525.4 (3)C1'—O1'—C5'—C4'58.08 (18)
C1'—N5—C51—C52174.66 (16)O4'—C4'—C5'—O1'179.65 (14)
C2—N1—C6—N6179.68 (18)C3'—C4'—C5'—O1'56.36 (18)
C2—N1—C6—C53.7 (3)O4'—C4'—C5'—C51'61.59 (19)
C4—C5—C6—N6174.52 (18)C3'—C4'—C5'—C51'175.12 (15)
N5—C5—C6—N61.7 (3)O1'—C5'—C51'—O5'80.28 (18)
C4—C5—C6—N11.8 (3)C4'—C5'—C51'—O5'159.24 (15)
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds