Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005404/cf6401sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005404/cf64014sup2.hkl |
CCDC reference: 269398
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2003).
C18H23NO6 | Dx = 1.282 Mg m−3 |
Mr = 349.37 | Melting point: 431 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.653 (2) Å | Cell parameters from 7664 reflections |
b = 9.780 (2) Å | θ = 3.8–26.6° |
c = 19.179 (4) Å | µ = 0.10 mm−1 |
V = 1810.6 (6) Å3 | T = 293 K |
Z = 4 | Cube, colourless |
F(000) = 744 | 0.3 × 0.3 × 0.3 mm |
Nonius KappaCDD area-detector diffractometer | 1811 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 26.6°, θmin = 3.8° |
φ scans | h = −12→12 |
13679 measured reflections | k = −12→12 |
2006 independent reflections | l = −22→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.139 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.053P] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
2006 reflections | Δρmax = 0.13 e Å−3 |
257 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.22 (6) |
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 | ||
C1 | 0.4868 (3) | 0.0482 (2) | −0.01239 (13) | 0.0546 (6) | |
H2 | 0.5728 | 0.0333 | 0.0081 | 0.063 (8)* | |
C3 | 0.4597 (3) | −0.0043 (3) | −0.07765 (15) | 0.0646 (7) | |
H4 | 0.5273 | −0.0536 | −0.1014 | 0.086 (11)* | |
C5 | 0.3305 (3) | 0.0171 (3) | −0.10766 (15) | 0.0672 (7) | |
H6 | 0.3106 | −0.0200 | −0.1512 | 0.065 (8)* | |
C7 | 0.2328 (3) | 0.0924 (3) | −0.07337 (15) | 0.0614 (6) | |
H8 | 0.1472 | 0.1080 | −0.0942 | 0.079 (10)* | |
C9 | 0.2599 (2) | 0.1458 (2) | −0.00783 (13) | 0.0532 (5) | |
H1 | 0.1926 | 0.1968 | 0.0152 | 0.060 (7)* | |
C11 | 0.3870 (2) | 0.1230 (2) | 0.02320 (11) | 0.0458 (5) | |
C12 | 0.4236 (2) | 0.1763 (2) | 0.09350 (11) | 0.0476 (5) | |
O13 | 0.5248 (2) | 0.1379 (2) | 0.12459 (10) | 0.0720 (6) | |
C14 | 0.3296 (3) | 0.2843 (3) | 0.12552 (12) | 0.0548 (6) | |
H15 | 0.3182 | 0.3595 | 0.0930 | 0.078 (10)* | |
H16 | 0.2390 | 0.2452 | 0.1345 | 0.061 (8)* | |
O17 | 0.3872 (2) | 0.33398 (17) | 0.18896 (8) | 0.0566 (5) | |
C18 | 0.3718 (2) | 0.2516 (2) | 0.24463 (10) | 0.0467 (5) | |
O19 | 0.3072 (2) | 0.1478 (2) | 0.24393 (9) | 0.0680 (6) | |
C20 | 0.4544 (2) | 0.3088 (2) | 0.30516 (10) | 0.0472 (5) | |
H21 | 0.4719 | 0.4066 | 0.2982 | 0.046 (6)* | |
C22 | 0.5910 (3) | 0.2319 (3) | 0.31411 (12) | 0.0603 (6) | |
H23 | 0.5824 | 0.1380 | 0.2985 | 0.081 (10)* | |
H24 | 0.6648 | 0.2759 | 0.2882 | 0.097 (12)* | |
C25 | 0.6184 (2) | 0.2384 (3) | 0.39200 (12) | 0.0525 (6) | |
H26 | 0.6554 | 0.3286 | 0.4042 | 0.041 (6)* | |
O27 | 0.7136 (2) | 0.1362 (2) | 0.41147 (11) | 0.0756 (7) | |
H27 | 0.724 (5) | 0.139 (5) | 0.459 (3) | 0.112 (14)* | |
C28 | 0.4754 (2) | 0.2214 (2) | 0.42329 (11) | 0.0512 (5) | |
H29 | 0.4524 | 0.1256 | 0.4292 | 0.070 (8)* | |
H30 | 0.4688 | 0.2671 | 0.4681 | 0.067 (8)* | |
N31 | 0.38526 (19) | 0.2859 (2) | 0.37192 (9) | 0.0491 (5) | |
C32 | 0.2633 (2) | 0.3437 (2) | 0.38851 (10) | 0.0496 (5) | |
O33 | 0.21212 (19) | 0.3396 (2) | 0.44657 (9) | 0.0679 (6) | |
O34 | 0.20672 (17) | 0.4024 (2) | 0.33270 (9) | 0.0619 (5) | |
C35 | 0.0774 (2) | 0.4815 (3) | 0.33630 (14) | 0.0567 (6) | |
C36 | −0.0411 (3) | 0.3930 (4) | 0.3582 (2) | 0.0909 (11) | |
H37 | −0.1265 | 0.4414 | 0.3513 | 0.150* | |
H38 | −0.0314 | 0.3698 | 0.4066 | 0.150* | |
H39 | −0.0415 | 0.3109 | 0.3307 | 0.150* | |
C40 | 0.0970 (5) | 0.5977 (4) | 0.3858 (3) | 0.132 (2) | |
H41 | 0.0087 | 0.6374 | 0.3966 | 0.150* | |
H42 | 0.1555 | 0.6655 | 0.3647 | 0.150* | |
H43 | 0.1395 | 0.5648 | 0.4278 | 0.150* | |
C44 | 0.0606 (5) | 0.5244 (6) | 0.2609 (3) | 0.1201 (18) | |
H45 | −0.0200 | 0.5813 | 0.2565 | 0.150* | |
H46 | 0.0501 | 0.4447 | 0.2322 | 0.150* | |
H47 | 0.1410 | 0.5746 | 0.2464 | 0.150* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0557 (12) | 0.0550 (11) | 0.0531 (12) | 0.0078 (10) | −0.0005 (10) | 0.0024 (9) |
C3 | 0.0763 (16) | 0.0583 (13) | 0.0592 (15) | 0.0082 (12) | 0.0055 (12) | −0.0110 (10) |
C5 | 0.0861 (19) | 0.0591 (13) | 0.0563 (14) | −0.0056 (13) | −0.0123 (12) | −0.0130 (11) |
C7 | 0.0610 (13) | 0.0612 (12) | 0.0620 (14) | −0.0038 (11) | −0.0147 (11) | −0.0021 (11) |
C9 | 0.0491 (10) | 0.0559 (11) | 0.0546 (12) | −0.0004 (9) | −0.0047 (9) | 0.0002 (9) |
C11 | 0.0511 (10) | 0.0423 (9) | 0.0440 (10) | −0.0037 (8) | 0.0004 (8) | 0.0033 (7) |
C12 | 0.0462 (10) | 0.0527 (11) | 0.0439 (10) | −0.0016 (9) | −0.0023 (8) | 0.0086 (8) |
O13 | 0.0608 (10) | 0.0991 (14) | 0.0560 (10) | 0.0187 (10) | −0.0154 (8) | −0.0042 (10) |
C14 | 0.0641 (14) | 0.0610 (12) | 0.0392 (10) | 0.0083 (11) | −0.0107 (9) | −0.0002 (9) |
O17 | 0.0713 (10) | 0.0587 (9) | 0.0398 (8) | −0.0011 (8) | −0.0072 (7) | 0.0012 (6) |
C18 | 0.0435 (10) | 0.0589 (11) | 0.0379 (10) | 0.0000 (9) | 0.0036 (8) | −0.0002 (8) |
O19 | 0.0703 (11) | 0.0841 (12) | 0.0495 (9) | −0.0277 (11) | −0.0014 (8) | 0.0032 (8) |
C20 | 0.0453 (10) | 0.0582 (11) | 0.0379 (10) | 0.0003 (9) | 0.0025 (8) | −0.0027 (8) |
C22 | 0.0454 (11) | 0.0868 (17) | 0.0486 (13) | 0.0108 (11) | −0.0005 (9) | −0.0080 (11) |
C25 | 0.0439 (10) | 0.0649 (12) | 0.0487 (12) | 0.0051 (10) | −0.0087 (8) | −0.0098 (9) |
O27 | 0.0672 (11) | 0.1005 (15) | 0.0591 (11) | 0.0347 (12) | −0.0172 (9) | −0.0169 (10) |
C28 | 0.0529 (11) | 0.0594 (11) | 0.0414 (11) | 0.0026 (10) | −0.0050 (9) | 0.0009 (9) |
N31 | 0.0450 (9) | 0.0646 (10) | 0.0376 (9) | 0.0061 (8) | 0.0006 (7) | −0.0005 (7) |
C32 | 0.0462 (10) | 0.0645 (12) | 0.0381 (11) | 0.0009 (10) | 0.0014 (8) | −0.0053 (8) |
O33 | 0.0542 (9) | 0.1065 (14) | 0.0429 (9) | 0.0074 (10) | 0.0096 (7) | −0.0018 (9) |
O34 | 0.0480 (8) | 0.0910 (13) | 0.0467 (9) | 0.0198 (9) | 0.0030 (7) | 0.0023 (8) |
C35 | 0.0384 (10) | 0.0593 (12) | 0.0723 (15) | 0.0027 (10) | −0.0013 (10) | −0.0030 (11) |
C36 | 0.0527 (14) | 0.092 (2) | 0.128 (3) | −0.0134 (15) | −0.0049 (17) | 0.006 (2) |
C40 | 0.090 (2) | 0.078 (2) | 0.226 (6) | 0.018 (2) | −0.040 (3) | −0.066 (3) |
C44 | 0.072 (2) | 0.174 (4) | 0.114 (3) | 0.043 (3) | 0.002 (2) | 0.061 (3) |
C1—C3 | 1.378 (4) | C22—H24 | 0.970 |
C1—C11 | 1.389 (3) | C25—O27 | 1.408 (3) |
C1—H2 | 0.930 | C25—C28 | 1.514 (3) |
C3—C5 | 1.389 (4) | C25—H26 | 0.980 |
C3—H4 | 0.930 | O27—H27 | 0.92 (5) |
C5—C7 | 1.366 (4) | C28—N31 | 1.458 (3) |
C5—H6 | 0.930 | C28—H29 | 0.970 |
C7—C9 | 1.386 (4) | C28—H30 | 0.970 |
C7—H8 | 0.930 | N31—C32 | 1.344 (3) |
C9—C11 | 1.383 (3) | C32—O33 | 1.219 (3) |
C9—H1 | 0.930 | C32—O34 | 1.332 (3) |
C11—C12 | 1.488 (3) | O34—C35 | 1.470 (3) |
C12—O13 | 1.204 (3) | C35—C40 | 1.492 (5) |
C12—C14 | 1.522 (3) | C35—C36 | 1.495 (4) |
C14—O17 | 1.423 (3) | C35—C44 | 1.514 (5) |
C14—H15 | 0.970 | C36—H37 | 0.960 |
C14—H16 | 0.970 | C36—H38 | 0.960 |
O17—C18 | 1.346 (3) | C36—H39 | 0.960 |
C18—O19 | 1.191 (3) | C40—H41 | 0.960 |
C18—C20 | 1.516 (3) | C40—H42 | 0.960 |
C20—N31 | 1.461 (3) | C40—H43 | 0.960 |
C20—C22 | 1.527 (3) | C44—H45 | 0.960 |
C20—H21 | 0.980 | C44—H46 | 0.960 |
C22—C25 | 1.518 (3) | C44—H47 | 0.960 |
C22—H23 | 0.970 | ||
C3—C1—C11 | 120.8 (2) | O27—C25—C22 | 110.2 (2) |
C3—C1—H2 | 119.6 | C28—C25—C22 | 103.10 (17) |
C11—C1—H2 | 119.6 | O27—C25—H26 | 109.7 |
C1—C3—C5 | 119.3 (2) | C28—C25—H26 | 109.7 |
C1—C3—H4 | 120.3 | C22—C25—H26 | 109.7 |
C5—C3—H4 | 120.3 | C25—O27—H27 | 108 (3) |
C7—C5—C3 | 120.1 (2) | N31—C28—C25 | 103.22 (17) |
C7—C5—H6 | 119.9 | N31—C28—H29 | 111.1 |
C3—C5—H6 | 119.9 | C25—C28—H29 | 111.1 |
C5—C7—C9 | 120.6 (2) | N31—C28—H30 | 111.1 |
C5—C7—H8 | 119.7 | C25—C28—H30 | 111.1 |
C9—C7—H8 | 119.7 | H29—C28—H30 | 109.1 |
C11—C9—C7 | 119.8 (2) | C32—N31—C28 | 123.00 (18) |
C11—C9—H1 | 120.1 | C32—N31—C20 | 122.89 (18) |
C7—C9—H1 | 120.1 | C28—N31—C20 | 112.69 (17) |
C9—C11—C1 | 119.3 (2) | O33—C32—O34 | 125.6 (2) |
C9—C11—C12 | 123.0 (2) | O33—C32—N31 | 123.9 (2) |
C1—C11—C12 | 117.7 (2) | O34—C32—N31 | 110.52 (18) |
O13—C12—C11 | 122.1 (2) | C32—O34—C35 | 122.51 (18) |
O13—C12—C14 | 120.0 (2) | O34—C35—C40 | 108.8 (2) |
C11—C12—C14 | 117.84 (18) | O34—C35—C36 | 111.0 (2) |
O17—C14—C12 | 110.41 (19) | C40—C35—C36 | 111.1 (4) |
O17—C14—H15 | 109.6 | O34—C35—C44 | 101.1 (2) |
C12—C14—H15 | 109.6 | C40—C35—C44 | 114.2 (4) |
O17—C14—H16 | 109.6 | C36—C35—C44 | 110.3 (3) |
C12—C14—H16 | 109.6 | C35—C36—H37 | 109.5 |
H15—C14—H16 | 108.1 | C35—C36—H38 | 109.5 |
C18—O17—C14 | 115.52 (18) | H37—C36—H38 | 109.5 |
O19—C18—O17 | 123.97 (19) | C35—C36—H39 | 109.5 |
O19—C18—C20 | 126.78 (19) | H37—C36—H39 | 109.5 |
O17—C18—C20 | 109.18 (18) | H38—C36—H39 | 109.5 |
N31—C20—C18 | 111.97 (18) | C35—C40—H41 | 109.5 |
N31—C20—C22 | 102.73 (17) | C35—C40—H42 | 109.5 |
C18—C20—C22 | 110.99 (17) | H41—C40—H42 | 109.5 |
N31—C20—H21 | 110.3 | C35—C40—H43 | 109.5 |
C18—C20—H21 | 110.3 | H41—C40—H43 | 109.5 |
C22—C20—H21 | 110.3 | H42—C40—H43 | 109.5 |
C25—C22—C20 | 103.90 (18) | C35—C44—H45 | 109.5 |
C25—C22—H23 | 111.0 | C35—C44—H46 | 109.5 |
C20—C22—H23 | 111.0 | H45—C44—H46 | 109.5 |
C25—C22—H24 | 111.0 | C35—C44—H47 | 109.5 |
C20—C22—H24 | 111.0 | H45—C44—H47 | 109.5 |
H23—C22—H24 | 109.0 | H46—C44—H47 | 109.5 |
O27—C25—C28 | 114.3 (2) |