Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018104/cf6119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018104/cf6119Isup2.hkl |
CCDC reference: 176043
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.142
- Data-to-parameter ratio = 17.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was prepared according to the procedure of Ayerbe et al. (1998). The reaction gave a mixture of three diastereoismers, (3a–c), in the proportions 59:29:12, which were separated by flash chromatography (ethyl acetate/hexane, 1:10). Suitable crystals were obtained by evaporation of an ethanol solution (m.p. 454–455 K). Spectroscopic analysis: IR (KBr, ν cm-1): 3328, 1722, 1535, 1381; 1H NMR (CDCl3, δ, p.p.m.): 7.31–7.14 (m, 10H), 4.96 (sb, 1H), 4.59 (d, 1H, J = 11.5 Hz), 4.33 (d, 1H, J = 11.5 Hz), 3.81 (s, 3H), 3.71 (m, 3H), 2.52 (s, 1H), 1.30 (d, 3H, J = 5.3 Hz), 1.26 (s, 3H); 13C NMR (CDCl3, δ, p.p.m.): 174.8, 137.6, 135.7, 128.6, 128.3, 128.2, 127.6, 127.5, 127.1, 112.3, 94.6, 73.7, 70.6, 70.1, 58.3, 57.0, 52.7, 17.0, 13.7; analysis, calculated for C22H26N2O5: C 66.30, H 6.59, N 7.03%; found: C 65.99, H 6.56, N 7.08%.
All H atoms were initially located in a difference Fourier map. The methyl-H atoms were then constrained to an ideal geometry with C—H distances of 0.98 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. The position of the amine-H atom was refined freely along with an isotropic displacement parameter. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.95–1.00 Å and Uiso(H) = 1.2Ueq(C).
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2001).
C22H26N2O5 | F(000) = 848 |
Mr = 398.45 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/n | Melting point: 454 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.245 (2) Å | Cell parameters from 25 reflections |
b = 8.4082 (17) Å | θ = 17.0–19.5° |
c = 26.6330 (15) Å | µ = 0.09 mm−1 |
β = 94.802 (11)° | T = 173 K |
V = 2063.1 (6) Å3 | Prism, colourless |
Z = 4 | 0.50 × 0.32 × 0.22 mm |
Rigaku AFC-5R diffractometer | Rint = 0.020 |
Radiation source: Rigaku rotating anode generator | θmax = 27.5°, θmin = 2.5° |
Graphite monochromator | h = 0→12 |
ω scans | k = 0→10 |
5348 measured reflections | l = −34→34 |
4719 independent reflections | 3 standard reflections every 150 reflections |
2920 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.4415P] where P = (Fo2 + 2Fc2)/3 |
4719 reflections | (Δ/σ)max = 0.001 |
269 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C22H26N2O5 | V = 2063.1 (6) Å3 |
Mr = 398.45 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.245 (2) Å | µ = 0.09 mm−1 |
b = 8.4082 (17) Å | T = 173 K |
c = 26.6330 (15) Å | 0.50 × 0.32 × 0.22 mm |
β = 94.802 (11)° |
Rigaku AFC-5R diffractometer | Rint = 0.020 |
5348 measured reflections | 3 standard reflections every 150 reflections |
4719 independent reflections | intensity decay: none |
2920 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.27 e Å−3 |
4719 reflections | Δρmin = −0.19 e Å−3 |
269 parameters |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.4580 (0.0094) x - 2.4899 (0.0095) y + 22.4909 (0.0142) z = 3.6175 (0.0115) * 0.0073 (0.0011) C2 * -0.0069 (0.0011) C3 * 0.0047 (0.0007) C4 * -0.0050 (0.0008) N1 - 0.6987 (0.0027) C5 |
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 | ||
O1 | 0.61730 (17) | 0.9198 (2) | 0.07951 (7) | 0.0597 (5) | |
O2 | 0.7218 (2) | 1.0383 (2) | 0.14481 (7) | 0.0721 (5) | |
O6 | 0.80889 (18) | 0.4743 (2) | 0.00001 (5) | 0.0576 (5) | |
O7 | 0.65473 (18) | 0.3568 (2) | 0.04833 (5) | 0.0572 (4) | |
O10 | 0.59975 (15) | 0.68719 (16) | 0.18720 (4) | 0.0383 (3) | |
N1 | 0.95987 (18) | 0.6213 (2) | 0.08183 (6) | 0.0397 (4) | |
H1 | 1.008 (2) | 0.591 (3) | 0.0549 (9) | 0.053 (7)* | |
N2 | 0.7077 (2) | 0.9252 (2) | 0.11587 (7) | 0.0472 (5) | |
C2 | 0.8363 (2) | 0.5196 (2) | 0.09011 (7) | 0.0378 (5) | |
H2 | 0.8698 | 0.4299 | 0.1129 | 0.045* | |
C3 | 0.7304 (2) | 0.6274 (2) | 0.11770 (7) | 0.0345 (4) | |
H3 | 0.6410 | 0.6444 | 0.0945 | 0.041* | |
C4 | 0.8129 (2) | 0.7876 (2) | 0.12326 (7) | 0.0368 (4) | |
C5 | 0.9054 (2) | 0.7839 (2) | 0.07735 (7) | 0.0357 (4) | |
H5 | 0.8390 | 0.7926 | 0.0458 | 0.043* | |
C6 | 0.7655 (2) | 0.4513 (2) | 0.04074 (7) | 0.0393 (5) | |
C8 | 0.5836 (3) | 0.2781 (3) | 0.00460 (9) | 0.0622 (7) | |
H81 | 0.5491 | 0.3579 | −0.0204 | 0.093* | |
H82 | 0.5011 | 0.2162 | 0.0147 | 0.093* | |
H83 | 0.6527 | 0.2069 | −0.0101 | 0.093* | |
C9 | 0.6837 (2) | 0.5613 (2) | 0.16744 (7) | 0.0418 (5) | |
H9 | 0.7717 | 0.5408 | 0.1910 | 0.050* | |
C11 | 0.5888 (3) | 0.6765 (3) | 0.24016 (7) | 0.0466 (5) | |
H111 | 0.6864 | 0.6868 | 0.2582 | 0.056* | |
H112 | 0.5487 | 0.5714 | 0.2485 | 0.056* | |
C12 | 0.4914 (2) | 0.8065 (2) | 0.25670 (7) | 0.0372 (4) | |
C13 | 0.4452 (3) | 0.9301 (3) | 0.22514 (8) | 0.0530 (6) | |
H13 | 0.4788 | 0.9370 | 0.1925 | 0.064* | |
C14 | 0.3502 (3) | 1.0442 (3) | 0.24071 (9) | 0.0617 (7) | |
H14 | 0.3189 | 1.1284 | 0.2186 | 0.074* | |
C15 | 0.3009 (3) | 1.0360 (3) | 0.28824 (9) | 0.0529 (6) | |
H15 | 0.2344 | 1.1129 | 0.2986 | 0.063* | |
C16 | 0.3491 (2) | 0.9151 (3) | 0.32042 (8) | 0.0456 (5) | |
H16 | 0.3176 | 0.9101 | 0.3534 | 0.055* | |
C17 | 0.4431 (2) | 0.8014 (2) | 0.30466 (7) | 0.0390 (5) | |
H17 | 0.4753 | 0.7183 | 0.3270 | 0.047* | |
C18 | 0.5942 (3) | 0.4103 (3) | 0.16107 (9) | 0.0620 (7) | |
H181 | 0.5632 | 0.3776 | 0.1938 | 0.093* | |
H182 | 0.6529 | 0.3258 | 0.1476 | 0.093* | |
H183 | 0.5086 | 0.4301 | 0.1376 | 0.093* | |
C19 | 0.9070 (2) | 0.8094 (3) | 0.17272 (7) | 0.0505 (6) | |
H191 | 0.9637 | 0.9075 | 0.1712 | 0.076* | |
H192 | 0.9729 | 0.7185 | 0.1780 | 0.076* | |
H193 | 0.8447 | 0.8160 | 0.2007 | 0.076* | |
C20 | 1.0205 (2) | 0.9107 (3) | 0.07653 (7) | 0.0389 (5) | |
C21 | 1.1639 (2) | 0.8830 (3) | 0.09425 (8) | 0.0527 (6) | |
H21 | 1.1927 | 0.7816 | 0.1073 | 0.063* | |
C22 | 1.2667 (3) | 1.0073 (4) | 0.09275 (9) | 0.0648 (8) | |
H22 | 1.3649 | 0.9891 | 0.1048 | 0.078* | |
C23 | 1.2256 (3) | 1.1538 (4) | 0.07398 (9) | 0.0617 (7) | |
H23 | 1.2957 | 1.2361 | 0.0730 | 0.074* | |
C24 | 1.0837 (3) | 1.1827 (3) | 0.05655 (9) | 0.0564 (6) | |
H24 | 1.0554 | 1.2848 | 0.0440 | 0.068* | |
C25 | 0.9824 (2) | 1.0613 (3) | 0.05753 (8) | 0.0453 (5) | |
H25 | 0.8848 | 1.0809 | 0.0450 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0434 (9) | 0.0550 (10) | 0.0800 (12) | 0.0131 (8) | 0.0009 (8) | 0.0142 (9) |
O2 | 0.1003 (14) | 0.0404 (9) | 0.0794 (12) | 0.0098 (9) | 0.0309 (11) | −0.0150 (9) |
O6 | 0.0690 (11) | 0.0699 (11) | 0.0353 (8) | −0.0160 (9) | 0.0124 (7) | −0.0108 (7) |
O7 | 0.0670 (10) | 0.0668 (11) | 0.0397 (8) | −0.0202 (9) | 0.0149 (7) | −0.0151 (8) |
O10 | 0.0506 (8) | 0.0380 (8) | 0.0277 (6) | 0.0101 (6) | 0.0112 (6) | 0.0010 (6) |
N1 | 0.0416 (9) | 0.0425 (10) | 0.0359 (9) | 0.0082 (8) | 0.0091 (7) | −0.0085 (8) |
N2 | 0.0476 (11) | 0.0389 (10) | 0.0577 (12) | 0.0060 (9) | 0.0201 (9) | −0.0013 (9) |
C2 | 0.0453 (12) | 0.0386 (11) | 0.0301 (10) | 0.0079 (9) | 0.0061 (8) | −0.0043 (8) |
C3 | 0.0423 (11) | 0.0327 (10) | 0.0289 (9) | 0.0062 (9) | 0.0062 (8) | −0.0031 (8) |
C4 | 0.0388 (10) | 0.0378 (11) | 0.0345 (10) | 0.0060 (9) | 0.0077 (8) | −0.0065 (8) |
C5 | 0.0337 (10) | 0.0422 (11) | 0.0314 (9) | 0.0046 (9) | 0.0035 (8) | −0.0049 (8) |
C6 | 0.0461 (11) | 0.0378 (11) | 0.0349 (10) | 0.0063 (9) | 0.0084 (9) | −0.0064 (8) |
C8 | 0.0658 (16) | 0.0678 (17) | 0.0539 (14) | −0.0180 (14) | 0.0102 (12) | −0.0206 (13) |
C9 | 0.0551 (12) | 0.0379 (11) | 0.0337 (10) | 0.0132 (10) | 0.0112 (9) | −0.0006 (8) |
C11 | 0.0606 (13) | 0.0521 (13) | 0.0283 (10) | 0.0170 (11) | 0.0103 (9) | 0.0044 (9) |
C12 | 0.0408 (11) | 0.0388 (11) | 0.0325 (9) | 0.0050 (9) | 0.0060 (8) | −0.0007 (8) |
C13 | 0.0650 (15) | 0.0590 (14) | 0.0369 (11) | 0.0220 (12) | 0.0158 (10) | 0.0091 (10) |
C14 | 0.0743 (17) | 0.0571 (15) | 0.0544 (14) | 0.0285 (13) | 0.0087 (12) | 0.0093 (12) |
C15 | 0.0532 (13) | 0.0499 (14) | 0.0564 (14) | 0.0149 (11) | 0.0098 (11) | −0.0116 (11) |
C16 | 0.0480 (12) | 0.0511 (13) | 0.0394 (11) | 0.0000 (11) | 0.0142 (9) | −0.0089 (10) |
C17 | 0.0450 (11) | 0.0402 (11) | 0.0323 (9) | −0.0001 (9) | 0.0062 (8) | −0.0018 (9) |
C18 | 0.097 (2) | 0.0396 (13) | 0.0540 (14) | −0.0008 (13) | 0.0354 (14) | −0.0007 (11) |
C19 | 0.0539 (13) | 0.0635 (15) | 0.0344 (10) | 0.0000 (12) | 0.0067 (9) | −0.0123 (10) |
C20 | 0.0368 (10) | 0.0506 (13) | 0.0303 (9) | −0.0016 (9) | 0.0082 (8) | −0.0114 (9) |
C21 | 0.0392 (12) | 0.0730 (16) | 0.0462 (12) | 0.0030 (12) | 0.0061 (9) | −0.0090 (12) |
C22 | 0.0342 (12) | 0.109 (2) | 0.0514 (14) | −0.0076 (14) | 0.0067 (10) | −0.0191 (15) |
C23 | 0.0632 (16) | 0.0756 (19) | 0.0500 (14) | −0.0236 (14) | 0.0257 (12) | −0.0221 (13) |
C24 | 0.0644 (16) | 0.0588 (15) | 0.0490 (13) | −0.0124 (13) | 0.0236 (11) | −0.0137 (11) |
C25 | 0.0472 (12) | 0.0476 (13) | 0.0423 (11) | −0.0032 (10) | 0.0108 (9) | −0.0063 (10) |
O1—N2 | 1.226 (2) | C12—C13 | 1.382 (3) |
O2—N2 | 1.225 (2) | C12—C17 | 1.388 (3) |
O6—C6 | 1.203 (2) | C13—C14 | 1.387 (3) |
O7—C6 | 1.325 (3) | C13—H13 | 0.950 |
O7—C8 | 1.449 (3) | C14—C15 | 1.382 (3) |
O10—C11 | 1.425 (2) | C14—H14 | 0.950 |
O10—C9 | 1.438 (2) | C15—C16 | 1.379 (3) |
N1—C5 | 1.458 (3) | C15—H15 | 0.950 |
N1—C2 | 1.459 (3) | C16—C17 | 1.381 (3) |
N1—H1 | 0.91 (2) | C16—H16 | 0.950 |
N2—C4 | 1.513 (3) | C17—H17 | 0.950 |
C2—C6 | 1.531 (3) | C18—H181 | 0.980 |
C2—C3 | 1.563 (2) | C18—H182 | 0.980 |
C2—H2 | 1.000 | C18—H183 | 0.980 |
C3—C9 | 1.531 (3) | C19—H191 | 0.980 |
C3—C4 | 1.549 (3) | C19—H192 | 0.980 |
C3—H3 | 1.000 | C19—H193 | 0.980 |
C4—C19 | 1.527 (3) | C20—C21 | 1.389 (3) |
C4—C5 | 1.550 (2) | C20—C25 | 1.398 (3) |
C5—C20 | 1.508 (3) | C21—C22 | 1.415 (4) |
C5—H5 | 1.000 | C21—H21 | 0.950 |
C8—H81 | 0.980 | C22—C23 | 1.371 (4) |
C8—H82 | 0.980 | C22—H22 | 0.950 |
C8—H83 | 0.980 | C23—C24 | 1.376 (4) |
C9—C18 | 1.518 (3) | C23—H23 | 0.950 |
C9—H9 | 1.000 | C24—C25 | 1.387 (3) |
C11—C12 | 1.506 (3) | C24—H24 | 0.950 |
C11—H111 | 0.990 | C25—H25 | 0.950 |
C11—H112 | 0.990 | ||
C6—O7—C8 | 117.12 (17) | C12—C11—H112 | 109.7 |
C11—O10—C9 | 113.63 (14) | H111—C11—H112 | 108.2 |
C5—N1—C2 | 107.02 (15) | C13—C12—C17 | 118.41 (18) |
C5—N1—H1 | 112.6 (15) | C13—C12—C11 | 122.03 (17) |
C2—N1—H1 | 113.2 (15) | C17—C12—C11 | 119.55 (18) |
O2—N2—O1 | 123.8 (2) | C12—C13—C14 | 120.6 (2) |
O2—N2—C4 | 118.6 (2) | C12—C13—H13 | 119.7 |
O1—N2—C4 | 117.55 (17) | C14—C13—H13 | 119.7 |
N1—C2—C6 | 111.97 (16) | C15—C14—C13 | 120.3 (2) |
N1—C2—C3 | 105.08 (16) | C15—C14—H14 | 119.9 |
C6—C2—C3 | 112.47 (16) | C13—C14—H14 | 119.9 |
N1—C2—H2 | 109.1 | C16—C15—C14 | 119.5 (2) |
C6—C2—H2 | 109.1 | C16—C15—H15 | 120.3 |
C3—C2—H2 | 109.1 | C14—C15—H15 | 120.3 |
C9—C3—C4 | 113.88 (15) | C15—C16—C17 | 119.98 (19) |
C9—C3—C2 | 115.41 (16) | C15—C16—H16 | 120.0 |
C2—C3—C4 | 103.10 (15) | C17—C16—H16 | 120.0 |
C9—C3—H3 | 108.0 | C16—C17—C12 | 121.2 (2) |
C4—C3—H3 | 108.0 | C16—C17—H17 | 119.4 |
C2—C3—H3 | 108.0 | C12—C17—H17 | 119.4 |
N2—C4—C19 | 109.53 (17) | C9—C18—H181 | 109.5 |
N2—C4—C3 | 110.24 (15) | C9—C18—H182 | 109.5 |
C19—C4—C3 | 115.27 (17) | H181—C18—H182 | 109.5 |
N2—C4—C5 | 107.69 (16) | C9—C18—H183 | 109.5 |
C19—C4—C5 | 111.75 (16) | H181—C18—H183 | 109.5 |
C3—C4—C5 | 101.94 (14) | H182—C18—H183 | 109.5 |
N1—C5—C20 | 115.12 (16) | C4—C19—H191 | 109.5 |
N1—C5—C4 | 99.45 (16) | C4—C19—H192 | 109.5 |
C20—C5—C4 | 115.71 (16) | H191—C19—H192 | 109.5 |
N1—C5—H5 | 108.7 | C4—C19—H193 | 109.5 |
C20—C5—H5 | 108.7 | H191—C19—H193 | 109.5 |
C4—C5—H5 | 108.7 | H192—C19—H193 | 109.5 |
O6—C6—O7 | 123.68 (19) | C21—C20—C25 | 118.7 (2) |
O6—C6—C2 | 124.3 (2) | C21—C20—C5 | 122.1 (2) |
O7—C6—C2 | 111.97 (16) | C25—C20—C5 | 119.26 (18) |
O7—C8—H81 | 109.5 | C20—C21—C22 | 119.4 (2) |
O7—C8—H82 | 109.5 | C20—C21—H21 | 120.3 |
H81—C8—H82 | 109.5 | C22—C21—H21 | 120.3 |
O7—C8—H83 | 109.5 | C23—C22—C21 | 120.5 (2) |
H81—C8—H83 | 109.5 | C23—C22—H22 | 119.8 |
H82—C8—H83 | 109.5 | C21—C22—H22 | 119.8 |
O10—C9—C18 | 110.50 (18) | C22—C23—C24 | 120.6 (2) |
O10—C9—C3 | 104.44 (15) | C22—C23—H23 | 119.7 |
C18—C9—C3 | 113.42 (17) | C24—C23—H23 | 119.7 |
O10—C9—H9 | 109.4 | C23—C24—C25 | 119.3 (3) |
C18—C9—H9 | 109.4 | C23—C24—H24 | 120.3 |
C3—C9—H9 | 109.4 | C25—C24—H24 | 120.3 |
O10—C11—C12 | 109.70 (16) | C24—C25—C20 | 121.5 (2) |
O10—C11—H111 | 109.7 | C24—C25—H25 | 119.2 |
C12—C11—H111 | 109.7 | C20—C25—H25 | 119.2 |
O10—C11—H112 | 109.7 | ||
C5—N1—C2—C6 | 93.37 (18) | C3—C2—C6—O7 | −62.9 (2) |
C5—N1—C2—C3 | −29.00 (19) | C11—O10—C9—C18 | 78.8 (2) |
N1—C2—C3—C9 | −126.00 (18) | C11—O10—C9—C3 | −158.85 (17) |
C6—C2—C3—C9 | 111.9 (2) | C4—C3—C9—O10 | 55.7 (2) |
N1—C2—C3—C4 | −1.20 (18) | C2—C3—C9—O10 | 174.69 (16) |
C6—C2—C3—C4 | −123.25 (17) | C4—C3—C9—C18 | 176.07 (18) |
O2—N2—C4—C19 | 8.5 (3) | C2—C3—C9—C18 | −64.9 (2) |
O1—N2—C4—C19 | −174.99 (18) | C9—O10—C11—C12 | −176.35 (17) |
O2—N2—C4—C3 | 136.31 (19) | O10—C11—C12—C13 | −10.6 (3) |
O1—N2—C4—C3 | −47.1 (2) | O10—C11—C12—C17 | 167.90 (18) |
O2—N2—C4—C5 | −113.3 (2) | C17—C12—C13—C14 | −1.4 (4) |
O1—N2—C4—C5 | 63.3 (2) | C11—C12—C13—C14 | 177.1 (2) |
C9—C3—C4—N2 | −91.70 (19) | C12—C13—C14—C15 | 0.3 (4) |
C2—C3—C4—N2 | 142.51 (15) | C13—C14—C15—C16 | 1.2 (4) |
C9—C3—C4—C19 | 32.9 (2) | C14—C15—C16—C17 | −1.5 (4) |
C2—C3—C4—C19 | −92.87 (18) | C15—C16—C17—C12 | 0.3 (3) |
C9—C3—C4—C5 | 154.16 (16) | C13—C12—C17—C16 | 1.2 (3) |
C2—C3—C4—C5 | 28.37 (18) | C11—C12—C17—C16 | −177.42 (19) |
C2—N1—C5—C20 | 171.08 (15) | N1—C5—C20—C21 | −19.4 (3) |
C2—N1—C5—C4 | 46.76 (17) | C4—C5—C20—C21 | 95.9 (2) |
N2—C4—C5—N1 | −161.45 (15) | N1—C5—C20—C25 | 160.85 (17) |
C19—C4—C5—N1 | 78.2 (2) | C4—C5—C20—C25 | −83.9 (2) |
C3—C4—C5—N1 | −45.43 (17) | C25—C20—C21—C22 | 0.2 (3) |
N2—C4—C5—C20 | 74.6 (2) | C5—C20—C21—C22 | −179.60 (18) |
C19—C4—C5—C20 | −45.7 (2) | C20—C21—C22—C23 | 0.0 (3) |
C3—C4—C5—C20 | −169.34 (16) | C21—C22—C23—C24 | 0.3 (4) |
C8—O7—C6—O6 | 0.1 (3) | C22—C23—C24—C25 | −0.8 (3) |
C8—O7—C6—C2 | −176.78 (19) | C23—C24—C25—C20 | 1.0 (3) |
N1—C2—C6—O6 | 2.2 (3) | C21—C20—C25—C24 | −0.7 (3) |
C3—C2—C6—O6 | 120.2 (2) | C5—C20—C25—C24 | 179.12 (18) |
N1—C2—C6—O7 | 179.00 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6 | 0.91 (2) | 2.46 (2) | 2.778 (2) | 101.1 (16) |
N1—H1···O6i | 0.91 (2) | 2.39 (2) | 3.278 (2) | 164 (2) |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H26N2O5 |
Mr | 398.45 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.245 (2), 8.4082 (17), 26.6330 (15) |
β (°) | 94.802 (11) |
V (Å3) | 2063.1 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.32 × 0.22 |
Data collection | |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5348, 4719, 2920 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.142, 1.06 |
No. of reflections | 4719 |
No. of parameters | 269 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.19 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1999), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2001).
N1—C5 | 1.458 (3) | C2—C3 | 1.563 (2) |
N1—C2 | 1.459 (3) | C3—C4 | 1.549 (3) |
N2—C4 | 1.513 (3) | C4—C5 | 1.550 (2) |
C5—N1—C2 | 107.02 (15) | C3—C4—C5 | 101.94 (14) |
N1—C2—C3 | 105.08 (16) | N1—C5—C4 | 99.45 (16) |
C2—C3—C4 | 103.10 (15) | ||
C5—N1—C2—C3 | −29.00 (19) | C2—N1—C5—C4 | 46.76 (17) |
N1—C2—C3—C4 | −1.20 (18) | C3—C4—C5—N1 | −45.43 (17) |
C2—C3—C4—C5 | 28.37 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6 | 0.91 (2) | 2.46 (2) | 2.778 (2) | 101.1 (16) |
N1—H1···O6i | 0.91 (2) | 2.39 (2) | 3.278 (2) | 164 (2) |
Symmetry code: (i) −x+2, −y+1, −z. |
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The title compound, (3c), is one of three diastereoisomeric products, (3a-c), obtained from the [3 + 2]-cycloaddition of the chiral nitroalkene (1) with the silver azomethine ylide derived from imine (2) (Ayerbe et al., 1998). Diastereoisomer (3a) could not be isolated; its absolute configuration was assumed by analogy with the compounds obtained in our previous work (Ayerbe et al., 1998). Compound (3 b) did not give crystals that were suitable for X-ray diffraction. Its relative configuration was determined by NOE experiments. The minor diastereoisomer (3c) was successfully crystallized from ethanol and fully characterized.
The puckering parameters (Cremer & Pople, 1975) for the five-membered ring are: q2 = 0.463 (2) Å and ϕ2 = 321.4 (2)°. The latter parameter is close to a value (324°) that is appropriate for an envelope conformation. The envelope flap is formed by C5, which lies 0.699 (3) Å from the plane defined by atoms N1, C2, C3 and C4. This puckering causes significant contraction of the N1—C5—C4 angle (Table 1).
The amine group of the molecule forms long, weak bifurcated hydrogen bonds with the carbonyl O atom of the ester substituent (Table 2). One interaction is intramolecular and completes a closed five-membered loop with a graph set motif of S(5) (Bernstein et al., 1995). The second is an intermolecular interaction with a neighbouring molecule, which is related to the original molecule by a centre of inversion. The intermolecular interactions thus link the molecules into hydrogen-bonded dimers which have a graph set motif of R22(10).