organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021428/bt2095sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021428/bt2095Isup2.hkl |
CCDC reference: 614858
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
C21H26N2O8 | Dx = 1.205 Mg m−3 |
Mr = 434.44 | Melting point = 515–516 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 14.065 (1) Å | θ = 7–15° |
b = 30.189 (2) Å | µ = 0.09 mm−1 |
c = 5.6414 (3) Å | T = 293 K |
V = 2395.4 (3) Å3 | Prism, light brown |
Z = 4 | 0.32 × 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 scans | h = −16→16 |
5210 measured reflections | k = −35→35 |
2458 independent reflections | l = −6→6 |
1196 reflections with I > 2σ(I) | 3 standard reflections every 60 min |
Rint = 0.027 | intensity decay: 6% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H-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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O421 | 0.4565 (2) | 0.18881 (12) | 1.2053 (6) | 0.0568 (10) | |
O411 | 0.3735 (2) | 0.10437 (11) | 1.1299 (6) | 0.0564 (9) | |
O431 | 0.2309 (2) | 0.17852 (12) | 0.9050 (7) | 0.0613 (11) | |
N2 | 0.6271 (3) | 0.09534 (14) | 0.6224 (9) | 0.0600 (12) | |
N1 | 0.6425 (3) | 0.08373 (15) | 0.4124 (9) | 0.0657 (13) | |
C42 | 0.3930 (4) | 0.17930 (17) | 1.0081 (10) | 0.0536 (14) | |
H42 | 0.4080 | 0.1989 | 0.8748 | 0.064* | |
C43 | 0.2935 (3) | 0.18960 (17) | 1.0996 (10) | 0.0569 (14) | |
H43 | 0.2793 | 0.1704 | 1.2352 | 0.068* | |
C41 | 0.4044 (3) | 0.13208 (17) | 0.9329 (9) | 0.0516 (13) | |
H41 | 0.3634 | 0.1264 | 0.7957 | 0.062* | |
O441 | 0.3062 (3) | 0.26538 (14) | 0.9775 (8) | 0.0796 (12) | |
C421 | 0.5299 (4) | 0.2166 (2) | 1.1644 (12) | 0.0676 (17) | |
C4 | 0.5040 (4) | 0.11908 (18) | 0.8732 (11) | 0.0598 (14) | |
H4 | 0.5488 | 0.1190 | 0.9945 | 0.072* | |
C11 | 0.7382 (4) | 0.06972 (18) | 0.3729 (11) | 0.0605 (15) | |
O422 | 0.5428 (3) | 0.23474 (17) | 0.9783 (10) | 0.0986 (16) | |
C3 | 0.5321 (4) | 0.10777 (18) | 0.6588 (10) | 0.0602 (15) | |
H3 | 0.4894 | 0.1080 | 0.5329 | 0.072* | |
C44 | 0.2777 (4) | 0.2371 (2) | 1.1686 (12) | 0.0754 (18) | |
H44A | 0.2110 | 0.2418 | 1.2043 | 0.090* | |
H44B | 0.3144 | 0.2440 | 1.3093 | 0.090* | |
O412 | 0.2920 (4) | 0.06160 (15) | 0.8819 (10) | 0.1071 (18) | |
C15 | 0.8454 (5) | 0.0333 (2) | 0.1114 (14) | 0.084 (2) | |
H15 | 0.8561 | 0.0183 | −0.0302 | 0.100* | |
C16 | 0.7557 (4) | 0.0486 (2) | 0.1611 (13) | 0.0756 (18) | |
H16 | 0.7069 | 0.0447 | 0.0520 | 0.091* | |
C431 | 0.1524 (5) | 0.1539 (2) | 0.9560 (15) | 0.082 (2) | |
C12 | 0.8118 (4) | 0.07690 (19) | 0.5292 (11) | 0.0701 (17) | |
H12 | 0.8014 | 0.0919 | 0.6710 | 0.084* | |
C14 | 0.9188 (5) | 0.0394 (2) | 0.2633 (17) | 0.084 (2) | |
O432 | 0.1338 (4) | 0.1434 (2) | 1.1524 (11) | 0.130 (2) | |
C411 | 0.3189 (4) | 0.06925 (19) | 1.0781 (12) | 0.0665 (16) | |
C13 | 0.9007 (4) | 0.0617 (2) | 0.4726 (15) | 0.086 (2) | |
H13 | 0.9504 | 0.0664 | 0.5782 | 0.104* | |
C422 | 0.5897 (4) | 0.2220 (3) | 1.3796 (13) | 0.100 (2) | |
H42A | 0.6299 | 0.1965 | 1.3980 | 0.150* | |
H42B | 0.5495 | 0.2249 | 1.5163 | 0.150* | |
H42C | 0.6283 | 0.2481 | 1.3636 | 0.150* | |
C412 | 0.2950 (5) | 0.0436 (2) | 1.2943 (14) | 0.094 (2) | |
H41A | 0.2405 | 0.0565 | 1.3700 | 0.141* | |
H41B | 0.3480 | 0.0441 | 1.4015 | 0.141* | |
H41C | 0.2809 | 0.0135 | 1.2514 | 0.141* | |
C432 | 0.0982 (5) | 0.1432 (3) | 0.7367 (15) | 0.110 (3) | |
H43A | 0.0820 | 0.1123 | 0.7366 | 0.165* | |
H43B | 0.1365 | 0.1498 | 0.6004 | 0.165* | |
H43C | 0.0411 | 0.1606 | 0.7317 | 0.165* | |
C17 | 1.0186 (5) | 0.0230 (3) | 0.2064 (19) | 0.124 (3) | |
H17A | 1.0331 | −0.0022 | 0.3033 | 0.185* | |
H17B | 1.0637 | 0.0462 | 0.2377 | 0.185* | |
H17C | 1.0220 | 0.0148 | 0.0422 | 0.185* | |
C441 | 0.3483 (7) | 0.3025 (3) | 1.0243 (17) | 0.109 (3) | |
O442 | 0.3632 (8) | 0.3137 (3) | 1.2213 (14) | 0.211 (4) | |
C442 | 0.3767 (7) | 0.3279 (3) | 0.8163 (19) | 0.127 (3) | |
H44C | 0.3845 | 0.3584 | 0.8594 | 0.191* | |
H44D | 0.3285 | 0.3255 | 0.6964 | 0.191* | |
H44E | 0.4357 | 0.3165 | 0.7561 | 0.191* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O421 | 0.0535 (19) | 0.074 (2) | 0.043 (2) | −0.0112 (19) | −0.0024 (18) | −0.002 (2) |
O411 | 0.061 (2) | 0.061 (2) | 0.046 (2) | −0.0086 (18) | −0.001 (2) | 0.004 (2) |
O431 | 0.0529 (19) | 0.077 (2) | 0.054 (3) | 0.0004 (19) | −0.003 (2) | −0.001 (2) |
N2 | 0.059 (3) | 0.074 (3) | 0.047 (3) | 0.004 (2) | 0.004 (2) | −0.005 (3) |
N1 | 0.061 (3) | 0.084 (3) | 0.053 (3) | 0.007 (2) | 0.004 (3) | −0.002 (3) |
C42 | 0.049 (3) | 0.066 (4) | 0.045 (3) | −0.004 (3) | 0.003 (3) | −0.005 (3) |
C43 | 0.054 (3) | 0.071 (4) | 0.046 (3) | 0.003 (3) | 0.000 (3) | −0.004 (3) |
C41 | 0.054 (3) | 0.059 (3) | 0.042 (3) | 0.001 (2) | −0.005 (3) | −0.004 (3) |
O441 | 0.096 (3) | 0.068 (3) | 0.074 (3) | 0.000 (2) | −0.016 (3) | −0.004 (3) |
C421 | 0.068 (4) | 0.078 (4) | 0.057 (4) | −0.017 (3) | 0.000 (3) | 0.008 (4) |
C4 | 0.050 (3) | 0.078 (4) | 0.052 (3) | 0.004 (3) | −0.010 (3) | −0.003 (3) |
C11 | 0.059 (3) | 0.064 (3) | 0.059 (4) | 0.001 (3) | 0.007 (3) | 0.004 (3) |
O422 | 0.086 (3) | 0.133 (4) | 0.077 (3) | −0.052 (3) | −0.009 (3) | 0.024 (3) |
C3 | 0.053 (3) | 0.076 (4) | 0.052 (4) | 0.003 (3) | −0.004 (3) | −0.004 (3) |
C44 | 0.072 (4) | 0.096 (5) | 0.057 (4) | 0.009 (3) | −0.004 (4) | −0.013 (4) |
O412 | 0.154 (5) | 0.095 (3) | 0.072 (3) | −0.057 (3) | −0.016 (4) | −0.009 (3) |
C15 | 0.079 (4) | 0.086 (4) | 0.086 (5) | 0.007 (3) | 0.017 (5) | −0.022 (4) |
C16 | 0.068 (4) | 0.097 (5) | 0.062 (4) | 0.005 (3) | 0.003 (3) | −0.017 (4) |
C431 | 0.061 (4) | 0.100 (5) | 0.085 (6) | −0.012 (4) | 0.002 (4) | −0.018 (5) |
C12 | 0.064 (3) | 0.082 (4) | 0.064 (4) | −0.001 (3) | 0.002 (4) | −0.013 (3) |
C14 | 0.065 (4) | 0.072 (4) | 0.116 (7) | 0.010 (3) | 0.011 (5) | −0.001 (4) |
O432 | 0.092 (4) | 0.217 (6) | 0.082 (4) | −0.067 (4) | 0.007 (3) | 0.013 (4) |
C411 | 0.075 (4) | 0.061 (4) | 0.064 (4) | −0.011 (3) | −0.003 (4) | 0.000 (4) |
C13 | 0.061 (4) | 0.097 (5) | 0.101 (6) | 0.000 (3) | −0.008 (4) | −0.010 (5) |
C422 | 0.083 (4) | 0.150 (7) | 0.067 (5) | −0.050 (4) | −0.013 (4) | −0.003 (5) |
C412 | 0.114 (5) | 0.085 (5) | 0.083 (5) | −0.028 (4) | −0.003 (5) | 0.024 (4) |
C432 | 0.084 (5) | 0.141 (7) | 0.104 (6) | −0.020 (5) | −0.032 (5) | −0.021 (6) |
C17 | 0.073 (4) | 0.127 (6) | 0.170 (9) | 0.027 (4) | 0.028 (6) | −0.010 (7) |
C441 | 0.161 (8) | 0.084 (5) | 0.081 (6) | −0.018 (5) | −0.020 (6) | −0.016 (5) |
O442 | 0.359 (11) | 0.159 (6) | 0.115 (5) | −0.128 (7) | −0.009 (7) | −0.036 (5) |
C442 | 0.147 (7) | 0.104 (6) | 0.131 (8) | −0.016 (5) | −0.037 (7) | 0.032 (6) |
Geometric parameters (Å, º) top
O421—C421 | 1.350 (7) | C15—C16 | 1.373 (8) |
O421—C42 | 1.456 (6) | C15—H15 | 0.9300 |
O411—C411 | 1.342 (6) | C16—H16 | 0.9300 |
O411—C41 | 1.457 (6) | C431—O432 | 1.182 (9) |
O431—C431 | 1.361 (8) | C431—C432 | 1.488 (10) |
O431—C43 | 1.447 (6) | C12—C13 | 1.370 (9) |
N2—N1 | 1.254 (6) | C12—H12 | 0.9300 |
N2—C3 | 1.404 (7) | C14—C13 | 1.382 (10) |
N1—C11 | 1.427 (7) | C14—C17 | 1.522 (9) |
C42—C41 | 1.496 (7) | C411—C412 | 1.484 (9) |
C42—C43 | 1.524 (7) | C13—H13 | 0.9300 |
C42—H42 | 0.9800 | C422—H42A | 0.9600 |
C43—C44 | 1.501 (8) | C422—H42B | 0.9600 |
C43—H43 | 0.9800 | C422—H42C | 0.9600 |
C41—C4 | 1.493 (7) | C412—H41A | 0.9600 |
C41—H41 | 0.9800 | C412—H41B | 0.9600 |
O441—C441 | 1.293 (9) | C412—H41C | 0.9600 |
O441—C44 | 1.433 (8) | C432—H43A | 0.9600 |
C421—O422 | 1.198 (7) | C432—H43B | 0.9600 |
C421—C422 | 1.486 (9) | C432—H43C | 0.9600 |
C4—C3 | 1.318 (8) | C17—H17A | 0.9600 |
C4—H4 | 0.9300 | C17—H17B | 0.9600 |
C11—C16 | 1.377 (9) | C17—H17C | 0.9600 |
C11—C12 | 1.378 (8) | C441—O442 | 1.180 (10) |
C3—H3 | 0.9300 | C441—C442 | 1.458 (12) |
C44—H44A | 0.9700 | C442—H44C | 0.9600 |
C44—H44B | 0.9700 | C442—H44D | 0.9600 |
O412—C411 | 1.192 (7) | C442—H44E | 0.9600 |
C15—C14 | 1.354 (9) | ||
C421—O421—C42 | 117.4 (4) | O432—C431—O431 | 121.6 (7) |
C411—O411—C41 | 117.3 (4) | O432—C431—C432 | 127.4 (7) |
C431—O431—C43 | 117.4 (5) | O431—C431—C432 | 111.0 (7) |
N1—N2—C3 | 112.2 (5) | C13—C12—C11 | 119.0 (6) |
N2—N1—C11 | 113.1 (5) | C13—C12—H12 | 120.5 |
O421—C42—C41 | 109.8 (4) | C11—C12—H12 | 120.5 |
O421—C42—C43 | 105.3 (4) | C15—C14—C13 | 117.8 (6) |
C41—C42—C43 | 112.9 (4) | C15—C14—C17 | 121.7 (8) |
O421—C42—H42 | 109.6 | C13—C14—C17 | 120.5 (8) |
C41—C42—H42 | 109.6 | O412—C411—O411 | 122.5 (6) |
C43—C42—H42 | 109.6 | O412—C411—C412 | 126.2 (6) |
O431—C43—C44 | 109.1 (4) | O411—C411—C412 | 111.3 (6) |
O431—C43—C42 | 104.8 (4) | C12—C13—C14 | 122.1 (7) |
C44—C43—C42 | 114.7 (5) | C12—C13—H13 | 119.0 |
O431—C43—H43 | 109.4 | C14—C13—H13 | 119.0 |
C44—C43—H43 | 109.4 | C421—C422—H42A | 109.5 |
C42—C43—H43 | 109.4 | C421—C422—H42B | 109.5 |
O411—C41—C42 | 107.4 (4) | H42A—C422—H42B | 109.5 |
O411—C41—C4 | 107.5 (4) | C421—C422—H42C | 109.5 |
C42—C41—C4 | 114.5 (4) | H42A—C422—H42C | 109.5 |
O411—C41—H41 | 109.1 | H42B—C422—H42C | 109.5 |
C42—C41—H41 | 109.1 | C411—C412—H41A | 109.5 |
C4—C41—H41 | 109.1 | C411—C412—H41B | 109.5 |
C441—O441—C44 | 119.4 (6) | H41A—C412—H41B | 109.5 |
O422—C421—O421 | 123.4 (6) | C411—C412—H41C | 109.5 |
O422—C421—C422 | 125.5 (6) | H41A—C412—H41C | 109.5 |
O421—C421—C422 | 111.2 (6) | H41B—C412—H41C | 109.5 |
C3—C4—C41 | 123.8 (5) | C431—C432—H43A | 109.5 |
C3—C4—H4 | 118.1 | C431—C432—H43B | 109.5 |
C41—C4—H4 | 118.1 | H43A—C432—H43B | 109.5 |
C16—C11—C12 | 119.6 (5) | C431—C432—H43C | 109.5 |
C16—C11—N1 | 116.2 (6) | H43A—C432—H43C | 109.5 |
C12—C11—N1 | 124.2 (5) | H43B—C432—H43C | 109.5 |
C4—C3—N2 | 119.3 (5) | C14—C17—H17A | 109.5 |
C4—C3—H3 | 120.3 | C14—C17—H17B | 109.5 |
N2—C3—H3 | 120.3 | H17A—C17—H17B | 109.5 |
O441—C44—C43 | 109.5 (5) | C14—C17—H17C | 109.5 |
O441—C44—H44A | 109.8 | H17A—C17—H17C | 109.5 |
C43—C44—H44A | 109.8 | H17B—C17—H17C | 109.5 |
O441—C44—H44B | 109.8 | O442—C441—O441 | 121.4 (9) |
C43—C44—H44B | 109.8 | O442—C441—C442 | 123.9 (9) |
H44A—C44—H44B | 108.2 | O441—C441—C442 | 114.6 (8) |
C14—C15—C16 | 121.7 (7) | C441—C442—H44C | 109.5 |
C14—C15—H15 | 119.1 | C441—C442—H44D | 109.5 |
C16—C15—H15 | 119.1 | H44C—C442—H44D | 109.5 |
C15—C16—C11 | 119.9 (7) | C441—C442—H44E | 109.5 |
C15—C16—H16 | 120.1 | H44C—C442—H44E | 109.5 |
C11—C16—H16 | 120.1 | H44D—C442—H44E | 109.5 |