Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001940/dn6016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001940/dn6016Isup2.hkl |
CCDC reference: 182598
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.006 Å
- R factor = 0.032
- wR factor = 0.058
- Data-to-parameter ratio = 7.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.97 From the CIF: _reflns_number_total 2861 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3243 Completeness (_total/calc) 88.22% Alert B: < 90% complete (theta max?)
Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.723 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.97 From the CIF: _reflns_number_total 2861 From the CIF: _diffrn_reflns_limit_ max hkl 10. 11. 30. From the CIF: _diffrn_reflns_limit_ min hkl -10. -9. -34. TEST1: Expected hkl limits for theta max Calculated maximum hkl 11. 12. 36. Calculated minimum hkl -11. -12. -36. ALERT: Expected hkl max differ from CIF values REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.97 From the CIF: _reflns_number_total 2861 Count of symmetry unique reflns 3243 Completeness (_total/calc) 88.22% 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
1 Alert Level B = Potential problem
1 Alert Level C = Please check
(II) and (IV) were prepared as described for the D-enantiomers (Dix et al., 2001) Analysis of (IV), found: C 49.34, H 7.59, N 13.18%; calculated: C 49.20, H 7.31, N 13.24%. [α]D -291° (cl, CHCl3). Crystals from ethyl acetate/hexane.
Because of the lack of any significant anomalous dispersion effects, the absolute conformation cannot be determined from the diffraction experiment. Friedel pairs have been merged prior to refinement. All H atoms were introduced at calculated positions as riding atoms (C—H = 0.97–0.98 Å, using AFIX 37 for CH3, AFIX 43 for aromatic CH and AFIX 13 for CH), with a displacement parameter equal to 1.2 (CH) or 1.5(CH3) times that of the parent atom.
Data collection: MADNES (Pflugrath & Messerschmidt, 1990); cell refinement: MADNES; data reduction: MADNES; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON92 (Spek, 1992) and PLATON92 (Spek, 1992); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of one of the independent molecules of (IV), showing 50% probability displacement ellipsoids. |
C13H23N3O6 | Dx = 1.298 Mg m−3 |
Mr = 317.34 | Melting point = 88–89 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 250 reflections |
a = 10.065 (4) Å | θ = 2.1–25.0° |
b = 10.512 (16) Å | µ = 0.10 mm−1 |
c = 30.696 (10) Å | T = 150 K |
V = 3248 (5) Å3 | Block, colourless |
Z = 8 | 0.32 × 0.18 × 0.10 mm |
F(000) = 1360 |
Enraf-Nonius FAST system diffractometer | 1724 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR591 rotating anode | Rint = 0.073 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
see exptl_special_details scans | h = −10→10 |
11775 measured reflections | k = −9→11 |
2861 independent reflections | l = −34→30 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.058 | H-atom parameters constrained |
S = 0.72 | w = 1/[σ2(Fo2) + (0.0051P)2] where P = (Fo2 + 2Fc2)/3 |
2861 reflections | (Δ/σ)max = 0.027 |
409 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C13H23N3O6 | V = 3248 (5) Å3 |
Mr = 317.34 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 10.065 (4) Å | µ = 0.10 mm−1 |
b = 10.512 (16) Å | T = 150 K |
c = 30.696 (10) Å | 0.32 × 0.18 × 0.10 mm |
Enraf-Nonius FAST system diffractometer | 1724 reflections with I > 2σ(I) |
11775 measured reflections | Rint = 0.073 |
2861 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.058 | H-atom parameters constrained |
S = 0.72 | Δρmax = 0.14 e Å−3 |
2861 reflections | Δρmin = −0.15 e Å−3 |
409 parameters |
Experimental. Cell measurement and data collection using a FAST area detector system, details in Darr, Drake,Hursthouse and Malik, Inorg. Chem. 1993, 32, 5704. The data were collected by the EPSRC National X-Ray Crystallography Service(Professor M. Hursthouse) on their, now defunct, Nonius FAST diffractometer, while they were at Cardiff. They had set the instrument to theta = 25 °, setting error reduced this to 24.97 °. |
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. |
x | y | z | Uiso*/Ueq | ||
C1A | 0.0398 (4) | 0.5407 (3) | 0.20823 (13) | 0.0341 (11) | |
H1A | −0.0566 | 0.5257 | 0.2022 | 0.044* | |
O1A | 0.1111 (3) | 0.4259 (2) | 0.20226 (8) | 0.0364 (7) | |
C2A | 0.0583 (4) | 0.5759 (3) | 0.25646 (12) | 0.0270 (10) | |
H2A | 0.0034 | 0.6535 | 0.2621 | 0.035* | |
C3A | 0.2012 (4) | 0.6119 (3) | 0.26443 (12) | 0.0238 (10) | |
H3A | 0.2590 | 0.5360 | 0.2591 | 0.031* | |
O3A | 0.2157 (2) | 0.6518 (2) | 0.30893 (8) | 0.0268 (6) | |
C4A | 0.2411 (4) | 0.7167 (3) | 0.23397 (13) | 0.0240 (10) | |
H4A | 0.1843 | 0.7931 | 0.2395 | 0.031* | |
O4A | 0.3774 (3) | 0.7486 (2) | 0.24179 (8) | 0.0289 (7) | |
C5A | 0.2245 (4) | 0.6745 (3) | 0.18700 (13) | 0.0296 (10) | |
H5A | 0.2835 | 0.5999 | 0.1811 | 0.039* | |
O5A | 0.0876 (3) | 0.6385 (2) | 0.18049 (8) | 0.0338 (7) | |
C6A | 0.2530 (4) | 0.7788 (3) | 0.15447 (13) | 0.0430 (12) | |
H6A1 | 0.2340 | 0.7479 | 0.1250 | 0.056* | |
H6A2 | 0.3467 | 0.8034 | 0.1565 | 0.056* | |
H6A3 | 0.1968 | 0.8526 | 0.1608 | 0.056* | |
C7A | 0.0778 (5) | 0.3650 (4) | 0.16192 (14) | 0.0624 (15) | |
H7A1 | −0.0187 | 0.3546 | 0.1600 | 0.081* | |
H7A2 | 0.1206 | 0.2814 | 0.1606 | 0.081* | |
H7A3 | 0.1089 | 0.4175 | 0.1376 | 0.081* | |
N11A | 0.0057 (4) | 0.4734 (3) | 0.28472 (11) | 0.0383 (9) | |
N12A | 0.0863 (4) | 0.3844 (4) | 0.29113 (12) | 0.0427 (10) | |
N13A | 0.1521 (4) | 0.2985 (3) | 0.30025 (15) | 0.0665 (14) | |
C14A | 0.3525 (4) | 0.6849 (3) | 0.31841 (13) | 0.0306 (11) | |
O14A | 0.4356 (3) | 0.5802 (2) | 0.31104 (9) | 0.0355 (7) | |
C15A | 0.4140 (4) | 0.4712 (3) | 0.33933 (14) | 0.0507 (13) | |
H15A | 0.4595 | 0.4850 | 0.3672 | 0.066* | |
H15B | 0.4494 | 0.3945 | 0.3254 | 0.066* | |
H15C | 0.3186 | 0.4605 | 0.3445 | 0.066* | |
C16A | 0.3507 (4) | 0.7283 (3) | 0.36519 (11) | 0.0351 (11) | |
H16A | 0.3087 | 0.6629 | 0.3833 | 0.046* | |
H16B | 0.3003 | 0.8077 | 0.3675 | 0.046* | |
H16C | 0.4420 | 0.7424 | 0.3752 | 0.046* | |
C17A | 0.4024 (4) | 0.7873 (3) | 0.28585 (12) | 0.0286 (10) | |
O17A | 0.3261 (2) | 0.8975 (2) | 0.29593 (9) | 0.0343 (7) | |
C18A | 0.3519 (5) | 1.0064 (3) | 0.26991 (14) | 0.0487 (13) | |
H18A | 0.4422 | 1.0370 | 0.2757 | 0.063* | |
H18B | 0.2879 | 1.0734 | 0.2771 | 0.063* | |
H18C | 0.3435 | 0.9839 | 0.2391 | 0.063* | |
C19A | 0.5502 (4) | 0.8097 (3) | 0.28831 (13) | 0.0361 (11) | |
H19A | 0.5770 | 0.8683 | 0.2651 | 0.047* | |
H19B | 0.5971 | 0.7287 | 0.2848 | 0.047* | |
H19C | 0.5726 | 0.8468 | 0.3167 | 0.047* | |
C1B | 0.2397 (5) | 0.7960 (4) | −0.04450 (13) | 0.0357 (11) | |
H1B | 0.2619 | 0.7050 | −0.0506 | 0.046* | |
O1B | 0.3564 (3) | 0.8691 (2) | −0.04779 (9) | 0.0416 (8) | |
C2B | 0.1932 (4) | 0.8076 (3) | 0.00278 (12) | 0.0263 (10) | |
H2B | 0.1130 | 0.7522 | 0.0059 | 0.034* | |
C3B | 0.1481 (4) | 0.9436 (3) | 0.01098 (12) | 0.0267 (10) | |
H3B | 0.2251 | 1.0029 | 0.0076 | 0.035* | |
O3B | 0.0965 (2) | 0.9526 (2) | 0.05450 (8) | 0.0277 (7) | |
C4B | 0.0421 (4) | 0.9775 (3) | −0.02095 (13) | 0.0290 (11) | |
H4B | −0.0364 | 0.9206 | −0.0165 | 0.038* | |
O4B | 0.0033 (3) | 1.1076 (2) | −0.01350 (9) | 0.0327 (7) | |
C5B | 0.0916 (4) | 0.9638 (3) | −0.06753 (12) | 0.0343 (11) | |
H5B | 0.1653 | 1.0257 | −0.0730 | 0.045* | |
O5B | 0.1400 (3) | 0.8349 (2) | −0.07305 (8) | 0.0405 (8) | |
C6B | −0.0179 (5) | 0.9828 (4) | −0.10106 (13) | 0.0480 (13) | |
H6B1 | 0.0185 | 0.9705 | −0.1304 | 0.062* | |
H6B2 | −0.0537 | 1.0692 | −0.0985 | 0.062* | |
H6B3 | −0.0890 | 0.9209 | −0.0959 | 0.062* | |
C7B | 0.4261 (5) | 0.8501 (4) | −0.08829 (13) | 0.0587 (14) | |
H7B1 | 0.4457 | 0.7594 | −0.0920 | 0.076* | |
H7B2 | 0.5093 | 0.8985 | −0.0879 | 0.076* | |
H7B3 | 0.3705 | 0.8794 | −0.1125 | 0.076* | |
N11B | 0.2933 (4) | 0.7597 (3) | 0.03366 (11) | 0.0348 (10) | |
N12B | 0.3825 (4) | 0.8366 (3) | 0.04247 (11) | 0.0372 (10) | |
N13B | 0.4718 (4) | 0.8972 (3) | 0.05397 (13) | 0.0518 (11) | |
C14B | 0.0498 (4) | 1.0773 (3) | 0.06461 (13) | 0.0303 (11) | |
O14B | 0.1544 (3) | 1.1658 (2) | 0.06267 (9) | 0.0384 (8) | |
C15B | 0.2679 (4) | 1.1405 (4) | 0.09004 (14) | 0.0477 (13) | |
H15D | 0.2492 | 1.1693 | 0.1198 | 0.062* | |
H15E | 0.3455 | 1.1861 | 0.0787 | 0.062* | |
H15F | 0.2862 | 1.0489 | 0.0902 | 0.062* | |
C16B | −0.0121 (4) | 1.0656 (3) | 0.10942 (12) | 0.0390 (12) | |
H16D | 0.0548 | 1.0351 | 0.1301 | 0.051* | |
H16E | −0.0862 | 1.0052 | 0.1083 | 0.051* | |
H16F | −0.0449 | 1.1490 | 0.1188 | 0.051* | |
C17B | −0.0511 (4) | 1.1240 (3) | 0.02886 (14) | 0.0338 (11) | |
O17B | −0.1647 (3) | 1.0467 (2) | 0.03528 (9) | 0.0385 (8) | |
C18B | −0.2718 (4) | 1.0732 (4) | 0.00631 (15) | 0.0577 (15) | |
H18D | −0.3093 | 1.1569 | 0.0131 | 0.075* | |
H18E | −0.3406 | 1.0080 | 0.0096 | 0.075* | |
H18F | −0.2391 | 1.0730 | −0.0238 | 0.075* | |
C19B | −0.0830 (4) | 1.2656 (3) | 0.03333 (14) | 0.0431 (13) | |
H19D | −0.1355 | 1.2935 | 0.0082 | 0.056* | |
H19E | 0.0000 | 1.3143 | 0.0345 | 0.056* | |
H19F | −0.1337 | 1.2799 | 0.0601 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.031 (3) | 0.038 (3) | 0.033 (3) | −0.005 (2) | 0.002 (2) | −0.005 (2) |
O1A | 0.047 (2) | 0.0307 (16) | 0.0311 (18) | 0.0026 (13) | −0.0013 (16) | −0.0123 (13) |
C2A | 0.031 (3) | 0.030 (2) | 0.020 (2) | −0.0025 (19) | 0.002 (2) | −0.0035 (18) |
C3A | 0.026 (3) | 0.026 (2) | 0.019 (2) | 0.0006 (18) | −0.001 (2) | −0.0068 (18) |
O3A | 0.0250 (18) | 0.0323 (14) | 0.0232 (17) | −0.0047 (12) | −0.0028 (14) | −0.0020 (12) |
C4A | 0.021 (3) | 0.028 (2) | 0.023 (2) | 0.0004 (18) | 0.000 (2) | 0.0013 (19) |
O4A | 0.0255 (18) | 0.0384 (15) | 0.0228 (17) | −0.0025 (13) | −0.0001 (14) | −0.0065 (13) |
C5A | 0.026 (3) | 0.030 (2) | 0.033 (3) | 0.001 (2) | −0.003 (2) | 0.000 (2) |
O5A | 0.0293 (19) | 0.0425 (17) | 0.0296 (18) | 0.0021 (14) | −0.0044 (15) | −0.0004 (13) |
C6A | 0.043 (3) | 0.059 (3) | 0.027 (3) | 0.002 (2) | 0.002 (2) | 0.004 (2) |
C7A | 0.076 (4) | 0.058 (3) | 0.053 (4) | −0.002 (3) | −0.005 (3) | −0.034 (3) |
N11A | 0.036 (2) | 0.039 (2) | 0.040 (3) | −0.0089 (19) | −0.002 (2) | −0.0003 (18) |
N12A | 0.040 (3) | 0.045 (3) | 0.043 (3) | −0.018 (2) | 0.003 (2) | 0.003 (2) |
N13A | 0.063 (3) | 0.045 (2) | 0.092 (4) | −0.009 (2) | −0.006 (3) | 0.022 (2) |
C14A | 0.024 (3) | 0.034 (2) | 0.034 (3) | 0.002 (2) | −0.003 (2) | −0.004 (2) |
O14A | 0.0307 (19) | 0.0412 (17) | 0.0345 (19) | 0.0038 (13) | −0.0030 (15) | 0.0004 (14) |
C15A | 0.054 (3) | 0.048 (3) | 0.050 (3) | 0.003 (2) | −0.008 (3) | 0.013 (2) |
C16A | 0.040 (3) | 0.045 (2) | 0.020 (3) | −0.012 (2) | −0.005 (2) | 0.000 (2) |
C17A | 0.027 (3) | 0.036 (2) | 0.022 (3) | −0.003 (2) | 0.003 (2) | −0.0033 (19) |
O17A | 0.0399 (19) | 0.0265 (15) | 0.0366 (19) | −0.0002 (13) | 0.0112 (16) | −0.0024 (14) |
C18A | 0.067 (4) | 0.027 (2) | 0.052 (3) | −0.009 (2) | 0.012 (3) | −0.002 (2) |
C19A | 0.029 (3) | 0.046 (2) | 0.033 (3) | −0.006 (2) | 0.007 (2) | −0.007 (2) |
C1B | 0.048 (3) | 0.032 (2) | 0.027 (3) | 0.004 (2) | 0.003 (3) | 0.001 (2) |
O1B | 0.049 (2) | 0.0420 (17) | 0.0336 (19) | −0.0019 (16) | 0.0181 (17) | −0.0024 (14) |
C2B | 0.029 (3) | 0.024 (2) | 0.026 (3) | −0.0001 (18) | 0.002 (2) | −0.0015 (18) |
C3B | 0.036 (3) | 0.023 (2) | 0.021 (3) | −0.0029 (19) | 0.001 (2) | 0.0046 (18) |
O3B | 0.0357 (18) | 0.0260 (15) | 0.0214 (16) | 0.0057 (12) | 0.0031 (15) | −0.0010 (12) |
C4B | 0.035 (3) | 0.021 (2) | 0.031 (3) | −0.0023 (19) | −0.003 (2) | 0.0021 (18) |
O4B | 0.0394 (19) | 0.0280 (15) | 0.0309 (19) | 0.0026 (13) | 0.0007 (15) | 0.0066 (12) |
C5B | 0.045 (3) | 0.031 (2) | 0.028 (3) | −0.004 (2) | −0.001 (2) | 0.0061 (19) |
O5B | 0.066 (2) | 0.0344 (17) | 0.0212 (18) | −0.0049 (16) | −0.0056 (17) | −0.0014 (13) |
C6B | 0.066 (4) | 0.046 (3) | 0.032 (3) | −0.015 (2) | −0.014 (3) | 0.008 (2) |
C7B | 0.075 (4) | 0.065 (3) | 0.036 (3) | 0.005 (3) | 0.024 (3) | 0.003 (2) |
N11B | 0.040 (3) | 0.030 (2) | 0.034 (2) | 0.0043 (18) | 0.005 (2) | −0.0008 (17) |
N12B | 0.040 (3) | 0.043 (2) | 0.029 (2) | 0.017 (2) | 0.001 (2) | −0.0016 (19) |
N13B | 0.043 (3) | 0.060 (3) | 0.052 (3) | 0.007 (2) | −0.012 (2) | −0.002 (2) |
C14B | 0.028 (3) | 0.025 (2) | 0.038 (3) | 0.002 (2) | 0.002 (2) | −0.002 (2) |
O14B | 0.0315 (19) | 0.0291 (16) | 0.055 (2) | −0.0027 (14) | −0.0022 (17) | −0.0022 (14) |
C15B | 0.040 (3) | 0.055 (3) | 0.048 (3) | 0.006 (2) | −0.011 (3) | −0.015 (2) |
C16B | 0.045 (3) | 0.042 (3) | 0.031 (3) | 0.011 (2) | 0.006 (2) | −0.005 (2) |
C17B | 0.035 (3) | 0.031 (2) | 0.036 (3) | 0.002 (2) | 0.009 (2) | 0.007 (2) |
O17B | 0.0254 (19) | 0.0363 (16) | 0.054 (2) | −0.0024 (14) | −0.0008 (16) | 0.0140 (15) |
C18B | 0.029 (3) | 0.063 (3) | 0.082 (4) | −0.003 (2) | −0.016 (3) | 0.019 (3) |
C19B | 0.045 (3) | 0.030 (2) | 0.054 (3) | 0.009 (2) | 0.007 (3) | 0.005 (2) |
C1A—O1A | 1.416 (4) | C1B—O5B | 1.394 (5) |
C1A—O5A | 1.419 (4) | C1B—O1B | 1.407 (5) |
C1A—C2A | 1.537 (5) | C1B—C2B | 1.530 (5) |
O1A—C7A | 1.434 (4) | O1B—C7B | 1.441 (4) |
C2A—N11A | 1.481 (5) | C2B—N11B | 1.472 (5) |
C2A—C3A | 1.507 (5) | C2B—C3B | 1.521 (5) |
C3A—O3A | 1.436 (4) | C3B—O3B | 1.436 (4) |
C3A—C4A | 1.500 (5) | C3B—C4B | 1.492 (5) |
O3A—C14A | 1.449 (4) | O3B—C14B | 1.426 (4) |
C4A—O4A | 1.432 (4) | C4B—O4B | 1.441 (4) |
C4A—C5A | 1.518 (5) | C4B—C5B | 1.521 (5) |
O4A—C17A | 1.435 (4) | O4B—C17B | 1.421 (4) |
C5A—O5A | 1.443 (4) | C5B—O5B | 1.450 (4) |
C5A—C6A | 1.510 (5) | C5B—C6B | 1.521 (5) |
N11A—N12A | 1.254 (5) | N11B—N12B | 1.238 (4) |
N12A—N13A | 1.154 (4) | N12B—N13B | 1.157 (5) |
C14A—O14A | 1.400 (4) | C14B—O14B | 1.406 (4) |
C14A—C16A | 1.507 (5) | C14B—C16B | 1.515 (5) |
C14A—C17A | 1.553 (5) | C14B—C17B | 1.574 (5) |
O14A—C15A | 1.454 (4) | O14B—C15B | 1.443 (4) |
C17A—O17A | 1.423 (4) | C17B—O17B | 1.416 (4) |
C17A—C19A | 1.509 (5) | C17B—C19B | 1.530 (5) |
O17A—C18A | 1.420 (4) | O17B—C18B | 1.425 (4) |
O1A—C1A—O5A | 111.6 (3) | O5B—C1B—O1B | 113.3 (3) |
O1A—C1A—C2A | 105.5 (3) | O5B—C1B—C2B | 110.7 (3) |
O5A—C1A—C2A | 111.3 (3) | O1B—C1B—C2B | 106.3 (3) |
C1A—O1A—C7A | 111.9 (3) | C1B—O1B—C7B | 113.1 (3) |
N11A—C2A—C3A | 115.4 (3) | N11B—C2B—C3B | 114.8 (3) |
N11A—C2A—C1A | 110.2 (3) | N11B—C2B—C1B | 112.0 (3) |
C3A—C2A—C1A | 109.4 (3) | C3B—C2B—C1B | 108.9 (3) |
O3A—C3A—C4A | 110.5 (3) | O3B—C3B—C4B | 109.7 (3) |
O3A—C3A—C2A | 109.0 (3) | O3B—C3B—C2B | 108.9 (3) |
C4A—C3A—C2A | 109.8 (3) | C4B—C3B—C2B | 109.2 (3) |
C3A—O3A—C14A | 111.0 (3) | C14B—O3B—C3B | 112.5 (3) |
O4A—C4A—C3A | 108.9 (3) | O4B—C4B—C3B | 108.4 (3) |
O4A—C4A—C5A | 109.4 (3) | O4B—C4B—C5B | 109.1 (3) |
C3A—C4A—C5A | 110.4 (3) | C3B—C4B—C5B | 111.1 (3) |
C4A—O4A—C17A | 113.1 (3) | C17B—O4B—C4B | 111.3 (3) |
O5A—C5A—C6A | 106.3 (3) | O5B—C5B—C4B | 107.9 (3) |
O5A—C5A—C4A | 108.3 (3) | O5B—C5B—C6B | 106.7 (3) |
C6A—C5A—C4A | 113.3 (3) | C4B—C5B—C6B | 112.7 (4) |
C1A—O5A—C5A | 115.5 (3) | C1B—O5B—C5B | 116.2 (3) |
N12A—N11A—C2A | 113.8 (3) | N12B—N11B—C2B | 114.4 (3) |
N13A—N12A—N11A | 173.2 (5) | N13B—N12B—N11B | 171.7 (4) |
O14A—C14A—O3A | 110.3 (3) | O14B—C14B—O3B | 110.6 (3) |
O14A—C14A—C16A | 113.5 (3) | O14B—C14B—C16B | 113.6 (3) |
O3A—C14A—C16A | 104.7 (3) | O3B—C14B—C16B | 105.0 (3) |
O14A—C14A—C17A | 104.3 (3) | O14B—C14B—C17B | 104.3 (3) |
O3A—C14A—C17A | 110.1 (3) | O3B—C14B—C17B | 110.3 (3) |
C16A—C14A—C17A | 114.0 (3) | C16B—C14B—C17B | 113.1 (3) |
C14A—O14A—C15A | 115.7 (3) | C14B—O14B—C15B | 116.5 (3) |
O17A—C17A—O4A | 110.0 (3) | O17B—C17B—O4B | 111.7 (3) |
O17A—C17A—C19A | 113.2 (3) | O17B—C17B—C19B | 112.1 (3) |
O4A—C17A—C19A | 105.3 (3) | O4B—C17B—C19B | 106.3 (3) |
O17A—C17A—C14A | 104.5 (3) | O17B—C17B—C14B | 104.2 (3) |
O4A—C17A—C14A | 110.7 (3) | O4B—C17B—C14B | 110.6 (3) |
C19A—C17A—C14A | 113.3 (3) | C19B—C17B—C14B | 112.1 (3) |
C18A—O17A—C17A | 115.8 (3) | C17B—O17B—C18B | 114.3 (3) |
Experimental details
Crystal data | |
Chemical formula | C13H23N3O6 |
Mr | 317.34 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 10.065 (4), 10.512 (16), 30.696 (10) |
V (Å3) | 3248 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.32 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Enraf-Nonius FAST system diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11775, 2861, 1724 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.058, 0.72 |
No. of reflections | 2861 |
No. of parameters | 409 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 |
Computer programs: MADNES (Pflugrath & Messerschmidt, 1990), MADNES, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLUTON92 (Spek, 1992) and PLATON92 (Spek, 1992), SHELXL97.
There are two, essentially identical, independent molecules in the asymmetric unit of the title compound, (IV). The structure of one of these molecules is shown in Fig. 1. There are no unusual bond lengths or angles. Comparison with the structure of (III) (Barnes et al., 2002) shows that the original conformation is preserved at all centers except for inversion of the configuration at the reaction centre C2. In the absence of a heavy atom, the absolute conformation of (IV) could not be determined but the alternate assumption that the entire conformation had reversed apart from C2 is untenable.