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The title compound, C12H17N3O7, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. Both virtually identical mol­ecules exhibit the expected chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005106/fl6149sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005106/fl61492sup2.hkl
Contains datablock 2

CCDC reference: 269561

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.110
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - N5 .. 5.27 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
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 28.28 From the CIF: _reflns_number_total 4157 Count of symmetry unique reflns 4160 Completeness (_total/calc) 99.93% 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
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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,3,4-Tri-O-acetyl-β-L-fucopyranosyl azide top
Crystal data top
C12H17N3O7F(000) = 664
Mr = 315.29Dx = 1.333 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ybCell parameters from 6342 reflections
a = 10.8447 (6) Åθ = 2.7–30.6°
b = 8.3527 (5) ŵ = 0.11 mm1
c = 17.443 (1) ÅT = 200 K
β = 96.257 (1)°Block, colourless
V = 1570.62 (16) Å30.46 × 0.42 × 0.40 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
4157 independent reflections
Radiation source: fine-focus sealed tube3917 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 1414
Tmin = 0.868, Tmax = 0.96k = 1111
16017 measured reflectionsl = 2323
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) = 0.110H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0699P)2 + 0.1865P]
where P = (Fo2 + 2Fc2)/3
4157 reflections(Δ/σ)max < 0.001
405 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = 0.27 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
C10.93305 (17)0.4305 (3)0.57496 (11)0.0407 (4)
H11.01100.37070.56820.049*
C20.82932 (17)0.3102 (3)0.58071 (11)0.0374 (4)
H20.85410.23270.62330.045*
C30.80075 (16)0.2201 (2)0.50531 (11)0.0356 (4)
H30.87250.14910.49740.043*
C40.77867 (16)0.3345 (2)0.43771 (10)0.0361 (4)
H40.69990.39570.43980.043*
C50.88961 (17)0.4477 (3)0.43886 (11)0.0380 (4)
H50.96610.38260.43510.046*
C60.9563 (2)0.5361 (4)0.64552 (13)0.0545 (6)
H6A0.88590.60880.64790.082*
H6B1.03200.59870.64250.082*
H6C0.96610.46920.69190.082*
C70.6714 (2)0.3614 (3)0.66307 (13)0.0481 (5)
C80.5643 (2)0.4664 (4)0.67487 (14)0.0564 (6)
H8A0.57080.50150.72880.085*
H8B0.48690.40670.66260.085*
H8C0.56460.56000.64110.085*
C90.7082 (2)0.0255 (3)0.53588 (12)0.0457 (5)
C100.5883 (3)0.1121 (4)0.53651 (15)0.0668 (8)
H10A0.54960.08190.58260.100*
H10B0.60350.22780.53700.100*
H10C0.53300.08370.49030.100*
C110.67809 (18)0.2618 (3)0.31346 (11)0.0414 (4)
C120.6924 (2)0.1568 (4)0.24589 (13)0.0578 (6)
H12A0.76080.19640.21870.087*
H12B0.61540.15770.21080.087*
H12C0.71050.04710.26370.087*
N10.87655 (17)0.5628 (3)0.37515 (10)0.0464 (4)
N20.7918 (2)0.6596 (3)0.37832 (11)0.0503 (4)
N30.7199 (3)0.7564 (4)0.37460 (16)0.0817 (8)
O10.90401 (13)0.53370 (18)0.50904 (8)0.0397 (3)
O20.71909 (12)0.3963 (2)0.59695 (8)0.0412 (3)
O30.7145 (3)0.2628 (4)0.70717 (15)0.0982 (9)
O40.69081 (12)0.1234 (2)0.50590 (8)0.0433 (3)
O50.80795 (16)0.0760 (2)0.55997 (12)0.0598 (5)
O60.77384 (13)0.24026 (19)0.36858 (8)0.0422 (3)
O70.59591 (15)0.3540 (3)0.31968 (9)0.0626 (5)
C210.41387 (18)0.1436 (3)0.92317 (11)0.0416 (4)
H210.49280.20510.93460.050*
C220.30575 (17)0.2605 (3)0.91584 (11)0.0375 (4)
H220.31720.34130.87490.045*
C230.29754 (16)0.3448 (2)0.99233 (11)0.0359 (4)
H230.37100.41681.00330.043*
C240.29594 (16)0.2255 (3)1.05760 (10)0.0357 (4)
H240.21620.16431.05270.043*
C250.40663 (17)0.1117 (3)1.05714 (10)0.0377 (4)
H250.48450.17651.06470.045*
C260.4212 (3)0.0465 (4)0.85091 (13)0.0602 (7)
H26A0.34810.02290.84210.090*
H26B0.49640.01950.85680.090*
H26C0.42380.11870.80680.090*
C270.1248 (2)0.2083 (3)0.82833 (13)0.0495 (5)
C280.0126 (2)0.1050 (4)0.81386 (14)0.0614 (7)
H28A0.02970.01670.77960.092*
H28B0.05680.16880.78960.092*
H28C0.00890.06170.86290.092*
C290.1931 (2)0.5885 (3)0.96060 (12)0.0452 (5)
C300.0707 (3)0.6710 (4)0.95600 (18)0.0709 (8)
H30A0.01690.63050.91140.106*
H30B0.08260.78650.95030.106*
H30C0.03200.65021.00320.106*
C310.24280 (19)0.2720 (3)1.18562 (11)0.0434 (4)
C320.2743 (2)0.3784 (4)1.25386 (13)0.0561 (6)
H32A0.21720.35721.29250.084*
H32B0.26690.49061.23760.084*
H32C0.35960.35711.27620.084*
N40.41111 (18)0.0085 (2)1.11835 (10)0.0470 (4)
N50.3216 (2)0.1029 (3)1.11095 (11)0.0528 (5)
N60.2492 (3)0.1971 (4)1.11125 (15)0.0801 (8)
O110.40255 (13)0.03261 (19)0.98530 (8)0.0410 (3)
O120.19169 (13)0.1727 (2)0.89577 (8)0.0432 (3)
O130.1555 (2)0.3078 (4)0.78532 (13)0.0936 (9)
O140.18610 (12)0.4389 (2)0.99016 (8)0.0433 (3)
O150.28619 (16)0.6426 (2)0.94021 (11)0.0557 (4)
O160.31026 (13)0.31544 (19)1.12799 (8)0.0413 (3)
O170.17042 (17)0.1639 (3)1.18030 (10)0.0650 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0342 (8)0.0473 (11)0.0391 (9)0.0012 (8)0.0033 (7)0.0073 (8)
C20.0325 (8)0.0438 (10)0.0348 (8)0.0012 (7)0.0011 (6)0.0055 (8)
C30.0282 (7)0.0405 (10)0.0378 (8)0.0003 (7)0.0023 (6)0.0029 (8)
C40.0315 (8)0.0416 (10)0.0349 (8)0.0045 (7)0.0024 (6)0.0001 (7)
C50.0363 (8)0.0413 (10)0.0363 (8)0.0037 (8)0.0043 (7)0.0036 (8)
C60.0549 (12)0.0646 (14)0.0415 (11)0.0188 (12)0.0065 (9)0.0035 (11)
C70.0521 (11)0.0508 (12)0.0428 (10)0.0074 (10)0.0110 (8)0.0014 (10)
C80.0497 (11)0.0739 (16)0.0473 (11)0.0044 (12)0.0125 (9)0.0141 (12)
C90.0471 (11)0.0529 (12)0.0378 (9)0.0100 (10)0.0082 (8)0.0036 (9)
C100.0634 (14)0.082 (2)0.0540 (13)0.0317 (15)0.0043 (11)0.0134 (14)
C110.0389 (9)0.0510 (11)0.0341 (9)0.0039 (9)0.0031 (7)0.0038 (8)
C120.0637 (13)0.0681 (16)0.0407 (11)0.0003 (13)0.0015 (10)0.0112 (11)
N10.0491 (9)0.0507 (10)0.0405 (8)0.0039 (8)0.0097 (7)0.0088 (8)
N20.0583 (10)0.0529 (11)0.0393 (9)0.0056 (9)0.0027 (8)0.0089 (8)
N30.0919 (18)0.0813 (18)0.0720 (15)0.0400 (16)0.0099 (13)0.0241 (15)
O10.0408 (7)0.0404 (7)0.0372 (6)0.0002 (6)0.0007 (5)0.0034 (6)
O20.0369 (6)0.0521 (8)0.0348 (6)0.0039 (6)0.0041 (5)0.0042 (6)
O30.121 (2)0.0965 (18)0.0869 (15)0.0346 (16)0.0562 (15)0.0502 (15)
O40.0335 (6)0.0507 (9)0.0451 (7)0.0065 (6)0.0022 (5)0.0034 (7)
O50.0535 (9)0.0495 (10)0.0769 (12)0.0007 (8)0.0100 (8)0.0190 (9)
O60.0401 (7)0.0479 (8)0.0379 (7)0.0068 (6)0.0011 (5)0.0060 (6)
O70.0500 (8)0.0932 (15)0.0424 (8)0.0218 (10)0.0053 (6)0.0050 (9)
C210.0408 (9)0.0487 (11)0.0358 (9)0.0048 (9)0.0063 (7)0.0021 (8)
C220.0341 (8)0.0458 (11)0.0324 (8)0.0011 (8)0.0022 (6)0.0011 (8)
C230.0299 (7)0.0418 (10)0.0357 (8)0.0001 (7)0.0017 (6)0.0010 (8)
C240.0339 (8)0.0425 (10)0.0299 (8)0.0033 (7)0.0004 (6)0.0029 (7)
C250.0372 (8)0.0422 (10)0.0326 (8)0.0000 (8)0.0009 (7)0.0004 (8)
C260.0714 (15)0.0716 (16)0.0382 (10)0.0237 (14)0.0093 (10)0.0056 (11)
C270.0492 (11)0.0590 (13)0.0379 (9)0.0007 (10)0.0054 (8)0.0001 (10)
C280.0526 (12)0.0824 (19)0.0465 (12)0.0089 (13)0.0072 (10)0.0063 (13)
C290.0470 (11)0.0518 (12)0.0359 (9)0.0116 (9)0.0002 (8)0.0003 (9)
C300.0599 (14)0.081 (2)0.0705 (16)0.0317 (15)0.0029 (12)0.0121 (16)
C310.0412 (9)0.0560 (12)0.0322 (8)0.0053 (9)0.0008 (7)0.0034 (9)
C320.0566 (12)0.0692 (16)0.0416 (11)0.0088 (12)0.0018 (9)0.0143 (11)
N40.0532 (10)0.0477 (10)0.0387 (8)0.0027 (8)0.0019 (7)0.0053 (8)
N50.0726 (13)0.0503 (11)0.0365 (9)0.0029 (10)0.0105 (8)0.0004 (8)
N60.112 (2)0.0714 (16)0.0595 (13)0.0353 (17)0.0188 (13)0.0004 (13)
O110.0464 (7)0.0418 (7)0.0346 (6)0.0021 (6)0.0036 (5)0.0018 (6)
O120.0402 (7)0.0537 (9)0.0343 (6)0.0069 (6)0.0024 (5)0.0000 (6)
O130.0953 (16)0.1029 (19)0.0727 (13)0.0326 (15)0.0360 (12)0.0425 (14)
O140.0340 (6)0.0515 (9)0.0441 (7)0.0052 (6)0.0033 (5)0.0025 (7)
O150.0570 (9)0.0481 (9)0.0631 (10)0.0061 (8)0.0112 (8)0.0079 (8)
O160.0424 (7)0.0469 (8)0.0338 (6)0.0023 (6)0.0010 (5)0.0063 (6)
O170.0667 (10)0.0877 (14)0.0422 (8)0.0248 (11)0.0139 (7)0.0066 (9)
Geometric parameters (Å, º) top
C1—O11.444 (2)C21—O111.441 (2)
C1—C61.513 (3)C21—C261.508 (3)
C1—C21.520 (3)C21—C221.521 (3)
C1—H11.0000C21—H211.0000
C2—O21.449 (2)C22—O121.448 (2)
C2—C31.518 (3)C22—C231.519 (3)
C2—H21.0000C22—H221.0000
C3—O41.441 (2)C23—O141.439 (2)
C3—C41.516 (3)C23—C241.514 (3)
C3—H31.0000C23—H231.0000
C4—O61.436 (2)C24—O161.433 (2)
C4—C51.529 (3)C24—C251.532 (3)
C4—H41.0000C24—H241.0000
C5—O11.413 (2)C25—O111.413 (2)
C5—N11.464 (3)C25—N41.463 (3)
C5—H51.0000C25—H251.0000
C6—H6A0.9800C26—H26A0.9800
C6—H6B0.9800C26—H26B0.9800
C6—H6C0.9800C26—H26C0.9800
C7—O31.187 (3)C27—O131.191 (3)
C7—O21.346 (2)C27—O121.346 (3)
C7—C81.488 (4)C27—C281.490 (4)
C8—H8A0.9800C28—H28A0.9800
C8—H8B0.9800C28—H28B0.9800
C8—H8C0.9800C28—H28C0.9800
C9—O51.194 (3)C29—O151.195 (3)
C9—O41.354 (3)C29—O141.357 (3)
C9—C101.489 (3)C29—C301.490 (3)
C10—H10A0.9800C30—H30A0.9800
C10—H10B0.9800C30—H30B0.9800
C10—H10C0.9800C30—H30C0.9800
C11—O71.192 (3)C31—O171.194 (3)
C11—O61.348 (2)C31—O161.356 (3)
C11—C121.491 (3)C31—C321.495 (3)
C12—H12A0.9800C32—H32A0.9800
C12—H12B0.9800C32—H32B0.9800
C12—H12C0.9800C32—H32C0.9800
N1—N21.230 (3)N4—N51.246 (3)
N2—N31.120 (3)N5—N61.112 (3)
O1—C1—C6107.60 (18)O11—C21—C26107.4 (2)
O1—C1—C2110.40 (14)O11—C21—C22110.38 (15)
C6—C1—C2113.00 (17)C26—C21—C22112.67 (17)
O1—C1—H1108.6O11—C21—H21108.8
C6—C1—H1108.6C26—C21—H21108.8
C2—C1—H1108.6C22—C21—H21108.8
O2—C2—C3108.70 (14)O12—C22—C23108.46 (14)
O2—C2—C1108.46 (17)O12—C22—C21108.98 (17)
C3—C2—C1110.69 (15)C23—C22—C21110.00 (15)
O2—C2—H2109.7O12—C22—H22109.8
C3—C2—H2109.7C23—C22—H22109.8
C1—C2—H2109.7C21—C22—H22109.8
O4—C3—C4107.35 (14)O14—C23—C24107.51 (14)
O4—C3—C2111.26 (14)O14—C23—C22111.06 (14)
C4—C3—C2111.19 (17)C24—C23—C22111.24 (17)
O4—C3—H3109.0O14—C23—H23109.0
C4—C3—H3109.0C24—C23—H23109.0
C2—C3—H3109.0C22—C23—H23109.0
O6—C4—C3107.19 (16)O16—C24—C23106.88 (17)
O6—C4—C5107.86 (14)O16—C24—C25108.53 (14)
C3—C4—C5108.81 (14)C23—C24—C25109.33 (14)
O6—C4—H4110.9O16—C24—H24110.7
C3—C4—H4110.9C23—C24—H24110.7
C5—C4—H4110.9C25—C24—H24110.7
O1—C5—N1108.45 (17)O11—C25—N4108.77 (17)
O1—C5—C4109.77 (14)O11—C25—C24110.24 (14)
N1—C5—C4112.65 (16)N4—C25—C24112.70 (16)
O1—C5—H5108.6O11—C25—H25108.3
N1—C5—H5108.6N4—C25—H25108.3
C4—C5—H5108.6C24—C25—H25108.3
C1—C6—H6A109.5C21—C26—H26A109.5
C1—C6—H6B109.5C21—C26—H26B109.5
H6A—C6—H6B109.5H26A—C26—H26B109.5
C1—C6—H6C109.5C21—C26—H26C109.5
H6A—C6—H6C109.5H26A—C26—H26C109.5
H6B—C6—H6C109.5H26B—C26—H26C109.5
O3—C7—O2123.0 (2)O13—C27—O12122.9 (2)
O3—C7—C8125.2 (2)O13—C27—C28125.2 (2)
O2—C7—C8111.7 (2)O12—C27—C28111.9 (2)
C7—C8—H8A109.5C27—C28—H28A109.5
C7—C8—H8B109.5C27—C28—H28B109.5
H8A—C8—H8B109.5H28A—C28—H28B109.5
C7—C8—H8C109.5C27—C28—H28C109.5
H8A—C8—H8C109.5H28A—C28—H28C109.5
H8B—C8—H8C109.5H28B—C28—H28C109.5
O5—C9—O4122.89 (19)O15—C29—O14123.0 (2)
O5—C9—C10125.7 (2)O15—C29—C30125.9 (2)
O4—C9—C10111.4 (2)O14—C29—C30111.1 (2)
C9—C10—H10A109.5C29—C30—H30A109.5
C9—C10—H10B109.5C29—C30—H30B109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
C9—C10—H10C109.5C29—C30—H30C109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
O7—C11—O6123.14 (19)O17—C31—O16123.24 (19)
O7—C11—C12126.6 (2)O17—C31—C32127.1 (2)
O6—C11—C12110.29 (19)O16—C31—C32109.6 (2)
C11—C12—H12A109.5C31—C32—H32A109.5
C11—C12—H12B109.5C31—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C11—C12—H12C109.5C31—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
N2—N1—C5114.10 (17)N5—N4—C25113.28 (17)
N3—N2—N1172.2 (3)N6—N5—N4171.7 (3)
C5—O1—C1112.36 (16)C25—O11—C21111.66 (16)
C7—O2—C2117.49 (17)C27—O12—C22117.67 (18)
C9—O4—C3115.92 (15)C29—O14—C23115.56 (15)
C11—O6—C4118.72 (16)C31—O16—C24118.57 (16)
 

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