Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040141/cv2129sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040141/cv2129Isup2.hkl |
CCDC reference: 291413
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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H22O5 | F(000) = 632 |
Mr = 294.34 | Dx = 1.271 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 11.0158 (11) Å | Cell parameters from 23 reflections |
b = 11.4856 (9) Å | θ = 8–16.4° |
c = 12.9229 (17) Å | µ = 0.77 mm−1 |
β = 109.823 (9)° | T = 293 K |
V = 1538.2 (3) Å3 | Plate, light yellow |
Z = 4 | 0.36 × 0.25 × 0.08 mm |
Enraf–Nonius CAD-4 diffractometer | θmax = 76.6°, θmin = 4.3° |
non–profiled ω/2θ scans | h = −13→13 |
3384 measured reflections | k = −14→0 |
3236 independent reflections | l = 0→16 |
2685 reflections with I > 2σ(I) | 3 standard reflections every 120 min |
Rint = 0.025 | intensity decay: 6% |
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0754P)2 + 0.4441P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.048 | (Δ/σ)max < 0.001 |
wR(F2) = 0.147 | Δρmax = 0.38 e Å−3 |
S = 1.03 | Δρmin = −0.19 e Å−3 |
3236 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
279 parameters | Extinction coefficient: 0.0049 (7) |
0 restraints |
Experimental. 1H NMR and 13 C NMR spectra were recorded on Bruker AV 300 MHz, and IR spectrum was recorded on FT—IR ABB Bomem MB 102. IR (KBr): ν 2919, 2905, 2853, 1754, 1739, 1715, 1456, 1435 cm-1. IR (C2Cl4): ν 2908, 2852, 1765, 1745, 1714, 1452, 1435. IR (CH2Cl2): ν 1759, 1738, 1708, 1436. 1H NMR (CDCl3, 300 MHz): δ 1.68 (d, J = 12.5 Hz, 3H), 1.77 (d, J = 12.5 Hz, 3H), 1.80–1.88 (m, 6H), 2.07 (bs, 3H), 3.78 (s, 6H), 4.98 (s, 1H). 1H NMR (DMSO, 300 MHz): 1.63–1.68 (m, 6H), 1.72–1.74 (m, 6H), 1.98 (bs, 3H), 3.67 (s, 6H), 5.51 (s, 1H). 13C NMR (CDCl3, 75 MHz): 27.41, 35.99, 37.27, 47.61, 52.91, 58.39, 164.97, 202.75. |
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. |
x | y | z | Uiso*/Ueq | ||
C1A | 0.2746 (2) | 0.9097 (2) | 0.1234 (2) | 0.0709 (6) | |
C1B | 0.6051 (3) | 1.3447 (2) | 0.0241 (2) | 0.0718 (6) | |
C2A | 0.47300 (16) | 1.01045 (15) | 0.18463 (13) | 0.0480 (4) | |
C2B | 0.54324 (16) | 1.18233 (15) | 0.10431 (13) | 0.0489 (4) | |
C3 | 0.58019 (15) | 1.05971 (14) | 0.14881 (13) | 0.0437 (4) | |
C4 | 0.70804 (16) | 1.05394 (14) | 0.24579 (12) | 0.0460 (4) | |
C5 | 0.78800 (14) | 0.94408 (13) | 0.25748 (12) | 0.0411 (3) | |
C6 | 0.85854 (18) | 0.95186 (16) | 0.17242 (16) | 0.0533 (4) | |
C7 | 0.70634 (17) | 0.83267 (14) | 0.23380 (16) | 0.0492 (4) | |
C8 | 0.8889 (2) | 0.93753 (19) | 0.37310 (16) | 0.0629 (5) | |
C9 | 0.94495 (19) | 0.84474 (19) | 0.18337 (18) | 0.0639 (5) | |
C10 | 0.8635 (2) | 0.73563 (18) | 0.16109 (18) | 0.0621 (5) | |
C11 | 0.7931 (2) | 0.72604 (16) | 0.24412 (17) | 0.0570 (5) | |
C12 | 0.8903 (3) | 0.72017 (19) | 0.36027 (18) | 0.0715 (6) | |
C13 | 0.9741 (2) | 0.8296 (2) | 0.38260 (18) | 0.0749 (7) | |
C14 | 1.0436 (2) | 0.8394 (2) | 0.2985 (2) | 0.0798 (7) | |
H1A* | 0.224 (4) | 0.973 (4) | 0.140 (3) | 0.149 (14)* | |
H1A' | 0.220 (3) | 0.873 (2) | 0.054 (2) | 0.092 (8)* | |
H1A | 0.300 (3) | 0.851 (3) | 0.173 (3) | 0.109 (10)* | |
H1B' | 0.532 (3) | 1.342 (3) | −0.039 (3) | 0.117 (11)* | |
H1B | 0.599 (3) | 1.399 (3) | 0.075 (3) | 0.125 (12)* | |
H1B* | 0.684 (3) | 1.365 (3) | 0.010 (3) | 0.119 (11)* | |
H3 | 0.5874 (17) | 1.0124 (16) | 0.0906 (15) | 0.046 (4)* | |
H6A | 0.790 (2) | 0.9581 (17) | 0.0942 (18) | 0.059 (5)* | |
H6B | 0.910 (2) | 1.024 (2) | 0.1860 (19) | 0.074 (6)* | |
H7A | 0.659 (2) | 0.8263 (19) | 0.2864 (18) | 0.068 (6)* | |
H7B | 0.643 (2) | 0.8328 (19) | 0.1584 (19) | 0.064 (6)* | |
H8A | 0.941 (2) | 1.014 (2) | 0.3899 (19) | 0.073 (6)* | |
H8B | 0.8418 (19) | 0.9336 (17) | 0.4245 (18) | 0.059 (6)* | |
H9 | 0.991 (2) | 0.8528 (19) | 0.1276 (19) | 0.073 (6)* | |
H10A | 0.803 (2) | 0.739 (2) | 0.088 (2) | 0.070 (6)* | |
H10B | 0.920 (2) | 0.663 (2) | 0.167 (2) | 0.081 (7)* | |
H11 | 0.740 (2) | 0.656 (2) | 0.2267 (19) | 0.075 (7)* | |
H12A | 0.844 (2) | 0.715 (2) | 0.413 (2) | 0.082 (7)* | |
H12B | 0.943 (2) | 0.650 (2) | 0.369 (2) | 0.083 (7)* | |
H13 | 1.038 (3) | 0.828 (2) | 0.454 (2) | 0.100 (9)* | |
H14A | 1.097 (2) | 0.909 (2) | 0.312 (2) | 0.076 (7)* | |
H14B | 1.102 (2) | 0.769 (2) | 0.305 (2) | 0.081 (7)* | |
O1A | 0.38412 (12) | 0.95893 (12) | 0.10115 (10) | 0.0583 (4) | |
O1B | 0.63474 (13) | 1.23158 (11) | 0.07644 (11) | 0.0594 (4) | |
O2A | 0.46905 (15) | 1.01790 (15) | 0.27537 (11) | 0.0734 (4) | |
O2B | 0.44016 (16) | 1.22377 (15) | 0.09022 (18) | 0.0925 (6) | |
O3 | 0.74092 (15) | 1.13528 (12) | 0.30795 (11) | 0.0726 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0696 (13) | 0.0654 (13) | 0.0845 (16) | −0.0163 (11) | 0.0352 (12) | 0.0024 (12) |
C1B | 0.0872 (17) | 0.0588 (12) | 0.0686 (13) | 0.0008 (11) | 0.0253 (13) | 0.0174 (10) |
C2A | 0.0547 (9) | 0.0475 (8) | 0.0439 (8) | 0.0066 (7) | 0.0194 (7) | 0.0013 (7) |
C2B | 0.0489 (9) | 0.0529 (9) | 0.0448 (8) | 0.0077 (7) | 0.0158 (7) | 0.0022 (7) |
C3 | 0.0477 (8) | 0.0451 (8) | 0.0379 (7) | 0.0045 (6) | 0.0141 (6) | −0.0037 (6) |
C4 | 0.0528 (9) | 0.0438 (8) | 0.0385 (7) | 0.0015 (7) | 0.0114 (6) | −0.0037 (6) |
C5 | 0.0430 (8) | 0.0401 (8) | 0.0378 (7) | 0.0005 (6) | 0.0108 (6) | −0.0022 (6) |
C6 | 0.0520 (9) | 0.0539 (10) | 0.0587 (10) | −0.0036 (8) | 0.0247 (8) | 0.0049 (8) |
C7 | 0.0501 (9) | 0.0423 (8) | 0.0595 (10) | −0.0009 (7) | 0.0244 (8) | 0.0004 (7) |
C8 | 0.0697 (12) | 0.0620 (12) | 0.0438 (9) | 0.0151 (9) | 0.0021 (9) | −0.0068 (8) |
C9 | 0.0551 (10) | 0.0745 (13) | 0.0731 (12) | 0.0082 (9) | 0.0361 (10) | 0.0030 (10) |
C10 | 0.0710 (12) | 0.0579 (11) | 0.0595 (11) | 0.0146 (9) | 0.0251 (10) | −0.0069 (9) |
C11 | 0.0663 (11) | 0.0410 (9) | 0.0674 (11) | 0.0032 (8) | 0.0274 (9) | 0.0013 (8) |
C12 | 0.0960 (16) | 0.0589 (12) | 0.0619 (12) | 0.0297 (11) | 0.0297 (11) | 0.0156 (9) |
C13 | 0.0754 (13) | 0.0748 (14) | 0.0534 (11) | 0.0276 (11) | −0.0058 (10) | −0.0038 (10) |
C14 | 0.0462 (11) | 0.0823 (16) | 0.1020 (18) | 0.0114 (11) | 0.0136 (11) | −0.0083 (13) |
O1A | 0.0574 (7) | 0.0663 (8) | 0.0532 (7) | −0.0118 (6) | 0.0213 (6) | −0.0028 (6) |
O1B | 0.0603 (7) | 0.0531 (7) | 0.0680 (8) | 0.0041 (6) | 0.0262 (6) | 0.0092 (6) |
O2A | 0.0834 (10) | 0.0947 (11) | 0.0510 (7) | −0.0063 (8) | 0.0344 (7) | −0.0052 (7) |
O2B | 0.0728 (10) | 0.0812 (11) | 0.1372 (16) | 0.0318 (8) | 0.0537 (10) | 0.0417 (10) |
O3 | 0.0888 (10) | 0.0489 (7) | 0.0589 (8) | 0.0116 (7) | −0.0027 (7) | −0.0177 (6) |
C1A—H1A* | 0.98 (4) | C8—H8A | 1.02 (3) |
C1A—H1A' | 0.99 (3) | C9—C14 | 1.517 (3) |
C1A—H1A | 0.91 (3) | C9—H9 | 1.01 (2) |
C1B—H1B* | 0.98 (4) | C10—C9 | 1.511 (3) |
C1B—H1B | 0.93 (4) | C10—C11 | 1.527 (3) |
C1B—H1B' | 0.93 (4) | C10—H10A | 0.95 (2) |
C2B—O2B | 1.187 (2) | C10—H10B | 1.03 (3) |
C3—C2A | 1.516 (2) | C11—C12 | 1.521 (3) |
C3—C2B | 1.524 (2) | C11—H11 | 0.98 (2) |
C3—C4 | 1.537 (2) | C12—C13 | 1.528 (4) |
C3—H3 | 0.953 (19) | C12—H12A | 0.98 (3) |
C4—C5 | 1.517 (2) | C12—H12B | 0.98 (3) |
C5—C8 | 1.532 (2) | C13—H13 | 0.96 (3) |
C5—C6 | 1.549 (2) | C14—C13 | 1.530 (4) |
C6—C9 | 1.532 (3) | C14—H14B | 1.02 (3) |
C6—H6A | 1.04 (2) | C14—H14A | 0.98 (3) |
C6—H6B | 0.99 (2) | O1A—C1A | 1.447 (2) |
C7—C5 | 1.534 (2) | O1A—C2A | 1.325 (2) |
C7—C11 | 1.531 (2) | O1B—C1B | 1.450 (2) |
C7—H7B | 0.99 (2) | O1B—C2B | 1.308 (2) |
C7—H7A | 0.99 (2) | O2A—C2A | 1.191 (2) |
C8—C13 | 1.535 (3) | O3—C4 | 1.205 (2) |
C8—H8B | 0.97 (2) | ||
H1A*—C1A—H1A' | 107 (3) | C9—C14—H14A | 109.2 (14) |
H1A*—C1A—H1A | 117 (3) | C10—C11—C7 | 109.40 (15) |
H1A'—C1A—H1A | 106 (3) | C10—C11—H11 | 107.9 (14) |
H1B—C1B—H1B' | 114 (3) | C10—C9—C14 | 109.55 (19) |
H1B*—C1B—H1B | 105 (3) | C10—C9—C6 | 109.78 (16) |
H1B*—C1B—H1B' | 114 (3) | C10—C9—H9 | 110.2 (13) |
H6A—C6—H6B | 107.3 (17) | C11—C12—C13 | 109.15 (17) |
H7B—C7—H7A | 108.5 (17) | C11—C12—H12A | 109.4 (15) |
H8B—C8—H8A | 106.4 (18) | C11—C7—C5 | 110.08 (14) |
H10A—C10—H10B | 107.9 (19) | C11—C7—H7B | 107.3 (13) |
H12A—C12—H12B | 108 (2) | C11—C7—H7A | 109.9 (13) |
H14B—C14—H14A | 108.0 (19) | C11—C10—H10A | 110.4 (14) |
C2A—O1A—C1A | 116.62 (16) | C11—C10—H10B | 109.0 (13) |
C2A—C3—C2B | 108.92 (13) | C12—C13—C14 | 110.00 (19) |
C2A—C3—C4 | 109.16 (13) | C12—C13—C8 | 109.6 (2) |
C2A—C3—H3 | 108.1 (11) | C12—C13—H13 | 111.5 (17) |
C2B—C3—C4 | 113.67 (13) | C12—C11—C10 | 109.95 (18) |
C2B—O1B—C1B | 116.31 (17) | C12—C11—C7 | 109.33 (16) |
C2B—C3—H3 | 108.2 (11) | C12—C11—H11 | 110.9 (14) |
C4—C3—H3 | 108.7 (11) | C13—C12—H12A | 110.1 (15) |
C4—C5—C8 | 110.04 (13) | C11—C12—H12B | 110.0 (15) |
C4—C5—C7 | 113.11 (13) | C13—C12—H12B | 110.7 (15) |
C4—C5—C6 | 107.19 (13) | C13—C8—H8B | 111.2 (12) |
C5—C8—H8A | 109.4 (13) | C13—C8—H8A | 112.9 (13) |
C5—C8—C13 | 109.84 (15) | C13—C14—H14B | 109.7 (14) |
C5—C8—H8B | 106.9 (12) | C13—C14—H14A | 110.5 (14) |
C5—C6—H6B | 108.7 (14) | C14—C9—C6 | 109.80 (18) |
C5—C4—C3 | 117.25 (12) | C14—C9—H9 | 109.8 (13) |
C5—C7—H7B | 111.5 (13) | C14—C13—H13 | 107.9 (17) |
C5—C7—H7A | 109.6 (13) | C14—C13—C8 | 108.9 (2) |
C5—C6—H6A | 108.9 (12) | O1A—C2A—C3 | 110.79 (13) |
C6—C9—H9 | 107.6 (13) | O1A—C1A—H1A* | 109 (2) |
C7—C5—C6 | 107.93 (13) | O1A—C1A—H1A' | 106.3 (16) |
C7—C11—H11 | 109.4 (14) | O1A—C1A—H1A | 110 (2) |
C8—C13—H13 | 108.9 (17) | O1B—C1B—H1B* | 103 (2) |
C8—C5—C7 | 109.63 (15) | O1B—C1B—H1B | 109 (2) |
C8—C5—C6 | 108.82 (15) | O1B—C1B—H1B' | 111 (2) |
C9—C14—C13 | 109.59 (17) | O1B—C2B—C3 | 111.81 (14) |
C9—C6—C5 | 109.49 (14) | O2A—C2A—O1A | 124.75 (17) |
C9—C6—H6A | 111.5 (11) | O2A—C2A—C3 | 124.46 (16) |
C9—C6—H6B | 110.9 (13) | O2B—C2B—O1B | 124.79 (17) |
C9—C10—C11 | 109.65 (16) | O2B—C2B—C3 | 123.22 (17) |
C9—C10—H10A | 109.2 (14) | O3—C4—C5 | 123.06 (15) |
C9—C10—H10B | 110.7 (13) | O3—C4—C3 | 119.69 (15) |
C9—C14—H14B | 109.8 (14) | ||
O3—C4—C3—C2a | −90.9 (2) | C4—C3—C2a—O1a | −147.9 (1) |
O3—C4—C3—C2b | 30.9 (2) | C4—C3—C2b—O1b | 55.3 (2) |
C4—C3—C2a—O2a | 32.6 (2) | C5—C4—C3—C2a | 89.7 (2) |
C4—C3—C2b—O2b | −129.5 (2) | C5—C4—C3—C2b | −148.5 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1a—H1a···O3i | 0.91 (3) | 2.54 (3) | 3.294 (3) | 140 (3) |
C1b—H1b···O2aii | 0.93 (4) | 2.67 (4) | 3.574 (4) | 164 (3) |
C7—H7a···O2bi | 0.99 (2) | 2.51 (3) | 3.439 (3) | 156 (2) |
C3—H3···O1aiii | 0.95 (2) | 2.62 (2) | 3.391 (2) | 138 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z. |