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The title compound, C14H19NO10, forms strong hydrogen bonds via amido groups in the [100] direction; soft C—H...O bonds also act to give chains along both [100] and [001], which combine to form a two-dimensional layer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003562/cf6155sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003562/cf6155Isup2.hkl
Contains datablock I

CCDC reference: 183810

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.093
  • Data-to-parameter ratio = 9.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.764 0.992 Tmin' and Tmax expected: 0.969 0.976 RR' = 0.775 Please check that your absorption correction is appropriate. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 2217 Count of symmetry unique reflns 2232 Completeness (_total/calc) 99.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEPIII for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2000) and SHELXL97.

1,2,3,4-tetra-acetyl-alpha-D-glucuronamide top
Crystal data top
C14H19NO10Dx = 1.430 Mg m3
Mr = 361.30Melting point = 365–366 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 5.5811 (2) ÅCell parameters from 9393 reflections
b = 16.9550 (6) Åθ = 2.9–27.5°
c = 17.7323 (6) ŵ = 0.12 mm1
V = 1677.96 (10) Å3T = 120 K
Z = 4Block, colourless
F(000) = 7600.25 × 0.20 × 0.20 mm
Data collection top
Nonius KappaCCD detector
diffractometer
2217 independent reflections
Radiation source: fine-focus sealed tube1926 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
h = 77
Tmin = 0.764, Tmax = 0.992k = 1921
10467 measured reflectionsl = 2222
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0584P)2 + 0.1398P]
where P = (Fo2 + 2Fc2)/3
2217 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.24 e Å3
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*/Ueq
O50.0564 (3)1.04864 (8)0.14352 (8)0.0195 (3)
C10.1298 (4)0.98603 (12)0.19046 (11)0.0198 (4)
H10.01110.96640.21980.024*
O10.3096 (3)1.01304 (9)0.24170 (8)0.0220 (3)
C70.2257 (4)1.05514 (13)0.30218 (12)0.0245 (5)
O70.0160 (3)1.06349 (10)0.31475 (9)0.0323 (4)
C80.4264 (5)1.08823 (15)0.34718 (13)0.0324 (6)
H8A0.38041.09020.40050.049*
H8B0.46301.14160.32940.049*
H8C0.56831.05470.34130.049*
C20.2334 (4)0.91835 (12)0.14366 (11)0.0193 (4)
H20.09880.89000.11810.023*
O20.3600 (3)0.86324 (9)0.19146 (8)0.0238 (3)
C90.2227 (5)0.80986 (13)0.22860 (12)0.0255 (5)
O80.0088 (3)0.80580 (11)0.22082 (9)0.0351 (4)
C100.3728 (5)0.76043 (14)0.28026 (13)0.0355 (6)
H10A0.30620.70700.28290.053*
H10B0.37340.78390.33080.053*
H10C0.53720.75800.26100.053*
C30.4123 (4)0.94516 (12)0.08413 (11)0.0181 (4)
H30.57230.95550.10750.022*
O30.4277 (3)0.88084 (8)0.03011 (8)0.0200 (3)
C110.6455 (4)0.86169 (12)0.00183 (11)0.0200 (4)
O90.8293 (3)0.89291 (10)0.02056 (9)0.0291 (4)
C120.6241 (5)0.79711 (13)0.05536 (12)0.0268 (5)
H12A0.55210.75050.03180.040*
H12B0.78350.78370.07460.040*
H12C0.52250.81490.09710.040*
C40.3236 (4)1.01771 (11)0.04228 (11)0.0175 (4)
H40.18381.00370.00970.021*
O40.5189 (3)1.04521 (8)0.00333 (7)0.0183 (3)
C130.4614 (4)1.07868 (13)0.07107 (11)0.0192 (4)
O100.2600 (3)1.08249 (9)0.09427 (8)0.0251 (4)
C140.6795 (4)1.10887 (14)0.11025 (12)0.0248 (5)
H14A0.70231.16470.09790.037*
H14B0.65971.10300.16490.037*
H14C0.81981.07870.09370.037*
C50.2503 (4)1.08038 (12)0.10023 (11)0.0185 (4)
H50.38891.09090.13460.022*
C60.1751 (4)1.15714 (12)0.06316 (12)0.0202 (4)
N10.0594 (4)1.16937 (12)0.05512 (11)0.0240 (4)
H1A0.169 (5)1.1319 (17)0.0703 (16)0.041 (8)*
H1B0.116 (5)1.2086 (19)0.0295 (17)0.047 (8)*
O60.3343 (3)1.20229 (9)0.04220 (9)0.0271 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0167 (7)0.0228 (7)0.0189 (6)0.0005 (6)0.0032 (6)0.0034 (6)
C10.0177 (10)0.0224 (10)0.0192 (9)0.0009 (9)0.0006 (9)0.0024 (8)
O10.0188 (8)0.0282 (7)0.0190 (7)0.0007 (7)0.0000 (6)0.0013 (6)
C70.0256 (12)0.0269 (11)0.0210 (10)0.0011 (10)0.0017 (9)0.0006 (9)
O70.0232 (9)0.0419 (10)0.0318 (8)0.0031 (8)0.0030 (8)0.0069 (7)
C80.0309 (13)0.0391 (13)0.0271 (11)0.0080 (11)0.0010 (10)0.0056 (10)
C20.0190 (10)0.0208 (10)0.0181 (9)0.0010 (8)0.0001 (8)0.0033 (8)
O20.0249 (8)0.0235 (7)0.0231 (7)0.0009 (7)0.0003 (7)0.0071 (6)
C90.0372 (14)0.0197 (11)0.0197 (10)0.0004 (10)0.0068 (10)0.0001 (8)
O80.0335 (10)0.0362 (9)0.0356 (9)0.0068 (8)0.0083 (8)0.0078 (8)
C100.0499 (16)0.0284 (12)0.0281 (11)0.0066 (12)0.0041 (13)0.0091 (10)
C30.0182 (10)0.0181 (10)0.0178 (9)0.0002 (9)0.0003 (8)0.0025 (7)
O30.0198 (7)0.0189 (7)0.0212 (7)0.0016 (6)0.0026 (6)0.0031 (6)
C110.0196 (10)0.0223 (10)0.0181 (9)0.0050 (9)0.0012 (9)0.0037 (8)
O90.0173 (8)0.0403 (9)0.0295 (8)0.0013 (7)0.0007 (7)0.0031 (7)
C120.0308 (12)0.0243 (10)0.0252 (11)0.0036 (11)0.0023 (10)0.0014 (9)
C40.0147 (10)0.0197 (9)0.0180 (9)0.0023 (8)0.0025 (8)0.0011 (8)
O40.0145 (7)0.0224 (7)0.0179 (6)0.0021 (6)0.0013 (6)0.0032 (6)
C130.0203 (11)0.0197 (10)0.0175 (9)0.0012 (9)0.0006 (9)0.0002 (8)
O100.0181 (8)0.0342 (9)0.0230 (8)0.0009 (7)0.0035 (6)0.0059 (7)
C140.0208 (11)0.0324 (11)0.0213 (10)0.0055 (10)0.0012 (9)0.0047 (9)
C50.0163 (10)0.0212 (10)0.0179 (9)0.0022 (9)0.0023 (8)0.0006 (8)
C60.0238 (11)0.0173 (10)0.0194 (9)0.0013 (9)0.0005 (9)0.0011 (8)
N10.0227 (10)0.0213 (9)0.0279 (10)0.0022 (8)0.0002 (8)0.0056 (8)
O60.0271 (9)0.0207 (7)0.0333 (8)0.0030 (7)0.0008 (7)0.0032 (7)
Geometric parameters (Å, º) top
O5—C11.410 (2)C3—H31.000
O5—C51.432 (2)O3—C111.355 (2)
C1—O11.429 (2)C11—O91.201 (3)
C1—C21.530 (3)C11—C121.497 (3)
C1—H11.000C12—H12A0.980
O1—C71.371 (3)C12—H12B0.980
C7—O71.200 (3)C12—H12C0.980
C7—C81.485 (3)C4—O41.435 (2)
C8—H8A0.980C4—C51.534 (3)
C8—H8B0.980C4—H41.000
C8—H8C0.980O4—C131.367 (2)
C2—O21.446 (2)C13—O101.198 (3)
C2—C31.522 (3)C13—C141.492 (3)
C2—H21.000C14—H14A0.980
O2—C91.356 (3)C14—H14B0.980
C9—O81.204 (3)C14—H14C0.980
C9—C101.498 (3)C5—C61.517 (3)
C10—H10A0.980C5—H51.000
C10—H10B0.980C6—O61.231 (3)
C10—H10C0.980C6—N11.332 (3)
C3—O31.454 (2)N1—H1A0.92 (3)
C3—C41.519 (3)N1—H1B0.87 (3)
C1—O5—C5112.31 (16)C11—O3—C3118.47 (16)
O5—C1—O1109.78 (15)O9—C11—O3123.95 (18)
O5—C1—C2110.76 (15)O9—C11—C12125.3 (2)
O1—C1—C2108.65 (17)O3—C11—C12110.74 (19)
O5—C1—H1109.2C11—C12—H12A109.5
O1—C1—H1109.2C11—C12—H12B109.5
C2—C1—H1109.2H12A—C12—H12B109.5
C7—O1—C1115.11 (15)C11—C12—H12C109.5
O7—C7—O1122.7 (2)H12A—C12—H12C109.5
O7—C7—C8126.3 (2)H12B—C12—H12C109.5
O1—C7—C8111.06 (19)O4—C4—C3106.92 (16)
C7—C8—H8A109.5O4—C4—C5110.79 (15)
C7—C8—H8B109.5C3—C4—C5108.70 (15)
H8A—C8—H8B109.5O4—C4—H4110.1
C7—C8—H8C109.5C3—C4—H4110.1
H8A—C8—H8C109.5C5—C4—H4110.1
H8B—C8—H8C109.5C13—O4—C4116.86 (16)
O2—C2—C3106.22 (17)O10—C13—O4122.98 (19)
O2—C2—C1110.57 (15)O10—C13—C14125.93 (18)
C3—C2—C1113.58 (17)O4—C13—C14111.09 (18)
O2—C2—H2108.8C13—C14—H14A109.5
C3—C2—H2108.8C13—C14—H14B109.5
C1—C2—H2108.8H14A—C14—H14B109.5
C9—O2—C2116.10 (18)C13—C14—H14C109.5
O8—C9—O2122.9 (2)H14A—C14—H14C109.5
O8—C9—C10126.4 (2)H14B—C14—H14C109.5
O2—C9—C10110.7 (2)O5—C5—C6110.20 (17)
C9—C10—H10A109.5O5—C5—C4107.48 (15)
C9—C10—H10B109.5C6—C5—C4112.21 (16)
H10A—C10—H10B109.5O5—C5—H5109.0
C9—C10—H10C109.5C6—C5—H5109.0
H10A—C10—H10C109.5C4—C5—H5109.0
H10B—C10—H10C109.5O6—C6—N1125.5 (2)
O3—C3—C4107.74 (15)O6—C6—C5117.67 (19)
O3—C3—C2105.76 (16)N1—C6—C5116.85 (19)
C4—C3—C2111.53 (17)C6—N1—H1A120.9 (18)
O3—C3—H3110.6C6—N1—H1B122 (2)
C4—C3—H3110.6H1A—N1—H1B116 (3)
C2—C3—H3110.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O6i0.87 (3)1.99 (3)2.840 (3)165 (3)
C2—H2···O9ii1.002.293.168 (3)146
C8—H8C···O7iii0.982.553.366 (3)141
C12—H12C···O7iv0.982.603.392 (3)138
C14—H14A···O6v0.982.573.529 (3)166
C14—H14C···O10iii0.982.463.283 (3)142
N1—H1A···O50.92 (3)2.29 (3)2.658 (2)103 (2)
C3—H3···O91.002.362.734 (3)101
C4—H4···O101.002.322.682 (2)100
C5—H5···O11.002.362.776 (2)104
Symmetry codes: (i) x1/2, y+5/2, z; (ii) x1, y, z; (iii) x+1, y, z; (iv) x+1/2, y+2, z1/2; (v) x+1/2, y+5/2, z.
 

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