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In the title compound, C21H26N2O8, the configurations of the three chiral centres are known from the synthesis, corresponding to a D-arabino configuration. Both double bonds show the E configuration in the solid state. Packing of the mol­ecules is governed by normal van der Waals contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021428/bt2095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021428/bt2095Isup2.hkl
Contains datablock I

CCDC reference: 614858

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.046
  • wR factor = 0.166
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.77 Ratio
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.08 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C411 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C421 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C431 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C441 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
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 25.00 From the CIF: _reflns_number_total 2458 Count of symmetry unique reflns 2466 Completeness (_total/calc) 99.68% 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 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

(1E,3E)-4-(Tetra-O-acetyl-D-arabino-tetritol-1-yl)-1-(4-tolyl)-1,2-diaza- 1,3-butadiene top
Crystal data top
C21H26N2O8Dx = 1.205 Mg m3
Mr = 434.44Melting point = 515–516 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 14.065 (1) Åθ = 7–15°
b = 30.189 (2) ŵ = 0.09 mm1
c = 5.6414 (3) ÅT = 293 K
V = 2395.4 (3) Å3Prism, light brown
Z = 40.32 × 0.28 × 0.16 mm
F(000) = 920
Data collection top
Enraf–Nonius CAD-4
diffractometer
θmax = 25°, θmin = 2.5°
Non–profiled ω/2θ scansh = 1616
5210 measured reflectionsk = 3535
2458 independent reflectionsl = 66
1196 reflections with I > 2σ(I)3 standard reflections every 60 min
Rint = 0.027 intensity decay: 6%
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters not defined
S = 0.97 w = 1/[σ2(Fo2) + (0.0855P)2 + 0.3134P]
where P = (Fo2 + 2Fc2)/3
2458 reflections(Δ/σ)max = 0.009
280 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.17 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O4210.4565 (2)0.18881 (12)1.2053 (6)0.0568 (10)
O4110.3735 (2)0.10437 (11)1.1299 (6)0.0564 (9)
O4310.2309 (2)0.17852 (12)0.9050 (7)0.0613 (11)
N20.6271 (3)0.09534 (14)0.6224 (9)0.0600 (12)
N10.6425 (3)0.08373 (15)0.4124 (9)0.0657 (13)
C420.3930 (4)0.17930 (17)1.0081 (10)0.0536 (14)
H420.40800.19890.87480.064*
C430.2935 (3)0.18960 (17)1.0996 (10)0.0569 (14)
H430.27930.17041.23520.068*
C410.4044 (3)0.13208 (17)0.9329 (9)0.0516 (13)
H410.36340.12640.79570.062*
O4410.3062 (3)0.26538 (14)0.9775 (8)0.0796 (12)
C4210.5299 (4)0.2166 (2)1.1644 (12)0.0676 (17)
C40.5040 (4)0.11908 (18)0.8732 (11)0.0598 (14)
H40.54880.11900.99450.072*
C110.7382 (4)0.06972 (18)0.3729 (11)0.0605 (15)
O4220.5428 (3)0.23474 (17)0.9783 (10)0.0986 (16)
C30.5321 (4)0.10777 (18)0.6588 (10)0.0602 (15)
H30.48940.10800.53290.072*
C440.2777 (4)0.2371 (2)1.1686 (12)0.0754 (18)
H44A0.21100.24181.20430.090*
H44B0.31440.24401.30930.090*
O4120.2920 (4)0.06160 (15)0.8819 (10)0.1071 (18)
C150.8454 (5)0.0333 (2)0.1114 (14)0.084 (2)
H150.85610.01830.03020.100*
C160.7557 (4)0.0486 (2)0.1611 (13)0.0756 (18)
H160.70690.04470.05200.091*
C4310.1524 (5)0.1539 (2)0.9560 (15)0.082 (2)
C120.8118 (4)0.07690 (19)0.5292 (11)0.0701 (17)
H120.80140.09190.67100.084*
C140.9188 (5)0.0394 (2)0.2633 (17)0.084 (2)
O4320.1338 (4)0.1434 (2)1.1524 (11)0.130 (2)
C4110.3189 (4)0.06925 (19)1.0781 (12)0.0665 (16)
C130.9007 (4)0.0617 (2)0.4726 (15)0.086 (2)
H130.95040.06640.57820.104*
C4220.5897 (4)0.2220 (3)1.3796 (13)0.100 (2)
H42A0.62990.19651.39800.150*
H42B0.54950.22491.51630.150*
H42C0.62830.24811.36360.150*
C4120.2950 (5)0.0436 (2)1.2943 (14)0.094 (2)
H41A0.24050.05651.37000.141*
H41B0.34800.04411.40150.141*
H41C0.28090.01351.25140.141*
C4320.0982 (5)0.1432 (3)0.7367 (15)0.110 (3)
H43A0.08200.11230.73660.165*
H43B0.13650.14980.60040.165*
H43C0.04110.16060.73170.165*
C171.0186 (5)0.0230 (3)0.2064 (19)0.124 (3)
H17A1.03310.00220.30330.185*
H17B1.06370.04620.23770.185*
H17C1.02200.01480.04220.185*
C4410.3483 (7)0.3025 (3)1.0243 (17)0.109 (3)
O4420.3632 (8)0.3137 (3)1.2213 (14)0.211 (4)
C4420.3767 (7)0.3279 (3)0.8163 (19)0.127 (3)
H44C0.38450.35840.85940.191*
H44D0.32850.32550.69640.191*
H44E0.43570.31650.75610.191*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O4210.0535 (19)0.074 (2)0.043 (2)0.0112 (19)0.0024 (18)0.002 (2)
O4110.061 (2)0.061 (2)0.046 (2)0.0086 (18)0.001 (2)0.004 (2)
O4310.0529 (19)0.077 (2)0.054 (3)0.0004 (19)0.003 (2)0.001 (2)
N20.059 (3)0.074 (3)0.047 (3)0.004 (2)0.004 (2)0.005 (3)
N10.061 (3)0.084 (3)0.053 (3)0.007 (2)0.004 (3)0.002 (3)
C420.049 (3)0.066 (4)0.045 (3)0.004 (3)0.003 (3)0.005 (3)
C430.054 (3)0.071 (4)0.046 (3)0.003 (3)0.000 (3)0.004 (3)
C410.054 (3)0.059 (3)0.042 (3)0.001 (2)0.005 (3)0.004 (3)
O4410.096 (3)0.068 (3)0.074 (3)0.000 (2)0.016 (3)0.004 (3)
C4210.068 (4)0.078 (4)0.057 (4)0.017 (3)0.000 (3)0.008 (4)
C40.050 (3)0.078 (4)0.052 (3)0.004 (3)0.010 (3)0.003 (3)
C110.059 (3)0.064 (3)0.059 (4)0.001 (3)0.007 (3)0.004 (3)
O4220.086 (3)0.133 (4)0.077 (3)0.052 (3)0.009 (3)0.024 (3)
C30.053 (3)0.076 (4)0.052 (4)0.003 (3)0.004 (3)0.004 (3)
C440.072 (4)0.096 (5)0.057 (4)0.009 (3)0.004 (4)0.013 (4)
O4120.154 (5)0.095 (3)0.072 (3)0.057 (3)0.016 (4)0.009 (3)
C150.079 (4)0.086 (4)0.086 (5)0.007 (3)0.017 (5)0.022 (4)
C160.068 (4)0.097 (5)0.062 (4)0.005 (3)0.003 (3)0.017 (4)
C4310.061 (4)0.100 (5)0.085 (6)0.012 (4)0.002 (4)0.018 (5)
C120.064 (3)0.082 (4)0.064 (4)0.001 (3)0.002 (4)0.013 (3)
C140.065 (4)0.072 (4)0.116 (7)0.010 (3)0.011 (5)0.001 (4)
O4320.092 (4)0.217 (6)0.082 (4)0.067 (4)0.007 (3)0.013 (4)
C4110.075 (4)0.061 (4)0.064 (4)0.011 (3)0.003 (4)0.000 (4)
C130.061 (4)0.097 (5)0.101 (6)0.000 (3)0.008 (4)0.010 (5)
C4220.083 (4)0.150 (7)0.067 (5)0.050 (4)0.013 (4)0.003 (5)
C4120.114 (5)0.085 (5)0.083 (5)0.028 (4)0.003 (5)0.024 (4)
C4320.084 (5)0.141 (7)0.104 (6)0.020 (5)0.032 (5)0.021 (6)
C170.073 (4)0.127 (6)0.170 (9)0.027 (4)0.028 (6)0.010 (7)
C4410.161 (8)0.084 (5)0.081 (6)0.018 (5)0.020 (6)0.016 (5)
O4420.359 (11)0.159 (6)0.115 (5)0.128 (7)0.009 (7)0.036 (5)
C4420.147 (7)0.104 (6)0.131 (8)0.016 (5)0.037 (7)0.032 (6)
Geometric parameters (Å, º) top
O421—C4211.350 (7)C15—C161.373 (8)
O421—C421.456 (6)C15—H150.9300
O411—C4111.342 (6)C16—H160.9300
O411—C411.457 (6)C431—O4321.182 (9)
O431—C4311.361 (8)C431—C4321.488 (10)
O431—C431.447 (6)C12—C131.370 (9)
N2—N11.254 (6)C12—H120.9300
N2—C31.404 (7)C14—C131.382 (10)
N1—C111.427 (7)C14—C171.522 (9)
C42—C411.496 (7)C411—C4121.484 (9)
C42—C431.524 (7)C13—H130.9300
C42—H420.9800C422—H42A0.9600
C43—C441.501 (8)C422—H42B0.9600
C43—H430.9800C422—H42C0.9600
C41—C41.493 (7)C412—H41A0.9600
C41—H410.9800C412—H41B0.9600
O441—C4411.293 (9)C412—H41C0.9600
O441—C441.433 (8)C432—H43A0.9600
C421—O4221.198 (7)C432—H43B0.9600
C421—C4221.486 (9)C432—H43C0.9600
C4—C31.318 (8)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C11—C161.377 (9)C17—H17C0.9600
C11—C121.378 (8)C441—O4421.180 (10)
C3—H30.9300C441—C4421.458 (12)
C44—H44A0.9700C442—H44C0.9600
C44—H44B0.9700C442—H44D0.9600
O412—C4111.192 (7)C442—H44E0.9600
C15—C141.354 (9)
C421—O421—C42117.4 (4)O432—C431—O431121.6 (7)
C411—O411—C41117.3 (4)O432—C431—C432127.4 (7)
C431—O431—C43117.4 (5)O431—C431—C432111.0 (7)
N1—N2—C3112.2 (5)C13—C12—C11119.0 (6)
N2—N1—C11113.1 (5)C13—C12—H12120.5
O421—C42—C41109.8 (4)C11—C12—H12120.5
O421—C42—C43105.3 (4)C15—C14—C13117.8 (6)
C41—C42—C43112.9 (4)C15—C14—C17121.7 (8)
O421—C42—H42109.6C13—C14—C17120.5 (8)
C41—C42—H42109.6O412—C411—O411122.5 (6)
C43—C42—H42109.6O412—C411—C412126.2 (6)
O431—C43—C44109.1 (4)O411—C411—C412111.3 (6)
O431—C43—C42104.8 (4)C12—C13—C14122.1 (7)
C44—C43—C42114.7 (5)C12—C13—H13119.0
O431—C43—H43109.4C14—C13—H13119.0
C44—C43—H43109.4C421—C422—H42A109.5
C42—C43—H43109.4C421—C422—H42B109.5
O411—C41—C42107.4 (4)H42A—C422—H42B109.5
O411—C41—C4107.5 (4)C421—C422—H42C109.5
C42—C41—C4114.5 (4)H42A—C422—H42C109.5
O411—C41—H41109.1H42B—C422—H42C109.5
C42—C41—H41109.1C411—C412—H41A109.5
C4—C41—H41109.1C411—C412—H41B109.5
C441—O441—C44119.4 (6)H41A—C412—H41B109.5
O422—C421—O421123.4 (6)C411—C412—H41C109.5
O422—C421—C422125.5 (6)H41A—C412—H41C109.5
O421—C421—C422111.2 (6)H41B—C412—H41C109.5
C3—C4—C41123.8 (5)C431—C432—H43A109.5
C3—C4—H4118.1C431—C432—H43B109.5
C41—C4—H4118.1H43A—C432—H43B109.5
C16—C11—C12119.6 (5)C431—C432—H43C109.5
C16—C11—N1116.2 (6)H43A—C432—H43C109.5
C12—C11—N1124.2 (5)H43B—C432—H43C109.5
C4—C3—N2119.3 (5)C14—C17—H17A109.5
C4—C3—H3120.3C14—C17—H17B109.5
N2—C3—H3120.3H17A—C17—H17B109.5
O441—C44—C43109.5 (5)C14—C17—H17C109.5
O441—C44—H44A109.8H17A—C17—H17C109.5
C43—C44—H44A109.8H17B—C17—H17C109.5
O441—C44—H44B109.8O442—C441—O441121.4 (9)
C43—C44—H44B109.8O442—C441—C442123.9 (9)
H44A—C44—H44B108.2O441—C441—C442114.6 (8)
C14—C15—C16121.7 (7)C441—C442—H44C109.5
C14—C15—H15119.1C441—C442—H44D109.5
C16—C15—H15119.1H44C—C442—H44D109.5
C15—C16—C11119.9 (7)C441—C442—H44E109.5
C15—C16—H16120.1H44C—C442—H44E109.5
C11—C16—H16120.1H44D—C442—H44E109.5
 

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