Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302107X/ac6051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680302107X/ac6051Isup2.hkl |
CCDC reference: 225862
Data collection: COLLECT (Nonius, 1997-2002); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H20O5 | F(000) = 1248 |
Mr = 292.32 | Dx = 1.278 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3662 reflections |
a = 23.3022 (3) Å | θ = 1.0–27.5° |
b = 10.2248 (2) Å | µ = 0.10 mm−1 |
c = 15.0785 (3) Å | T = 120 K |
β = 122.273 (1)° | Prism, colorless |
V = 3037.60 (9) Å3 | 0.16 × 0.14 × 0.10 mm |
Z = 8 |
Nonius KappaCCD diffractometer | Rint = 0.016 |
CCD rotation images, thick slices scans | θmax = 25°, θmin = 3.2° |
5170 measured reflections | h = −27→27 |
2666 independent reflections | k = −12→12 |
2207 reflections with I > 2σ(I) | l = −17→17 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0472P)2 + 0.8048P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.033 | (Δ/σ)max < 0.001 |
wR(F2) = 0.090 | Δρmax = 0.19 e Å−3 |
S = 1.05 | Δρmin = −0.16 e Å−3 |
2666 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
271 parameters | Extinction coefficient: 0.0043 (7) |
0 restraints |
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 | ||
C13 | −0.17318 (8) | 0.34247 (15) | −0.33222 (12) | 0.0334 (3) | |
C15 | −0.05400 (8) | 0.52785 (13) | 0.08274 (13) | 0.0337 (3) | |
O20 | 0.19639 (4) | 0.32730 (9) | 0.38925 (7) | 0.0278 (2) | |
C16 | 0.11583 (7) | 0.05665 (14) | 0.00327 (12) | 0.0311 (3) | |
O19 | 0.10000 (4) | 0.14355 (9) | 0.06192 (7) | 0.0295 (2) | |
C10 | 0.08016 (7) | 0.30486 (13) | 0.18803 (10) | 0.0255 (3) | |
C7 | 0.03408 (6) | 0.18379 (12) | 0.01653 (10) | 0.0238 (3) | |
C8 | 0.02258 (6) | 0.26705 (12) | 0.08000 (9) | 0.0228 (3) | |
C6 | −0.01759 (6) | 0.14873 (12) | −0.08405 (10) | 0.0251 (3) | |
C1 | −0.19220 (6) | 0.23845 (13) | −0.28030 (10) | 0.0266 (3) | |
C9 | −0.04311 (6) | 0.31305 (12) | 0.03743 (9) | 0.0225 (3) | |
O18 | −0.05724 (4) | 0.39039 (9) | 0.09929 (7) | 0.0264 (2) | |
C12 | 0.16551 (6) | 0.22373 (12) | 0.37012 (10) | 0.0237 (3) | |
C5 | −0.08228 (6) | 0.19751 (12) | −0.12295 (9) | 0.0241 (3) | |
C4 | −0.09670 (6) | 0.28131 (12) | −0.06393 (9) | 0.0232 (3) | |
C2 | −0.21218 (7) | 0.30046 (13) | −0.20982 (10) | 0.0279 (3) | |
O17 | −0.13316 (4) | 0.15304 (8) | −0.21922 (7) | 0.0281 (2) | |
C3 | −0.16684 (6) | 0.32264 (13) | −0.10918 (10) | 0.0264 (3) | |
C11 | 0.10199 (6) | 0.19405 (13) | 0.26714 (10) | 0.0255 (3) | |
C14 | −0.24721 (8) | 0.14828 (15) | −0.36001 (12) | 0.0365 (4) | |
O21 | 0.18620 (5) | 0.12654 (9) | 0.43794 (7) | 0.0310 (3) | |
H15A | −0.0075 (8) | 0.5516 (15) | 0.0955 (12) | 0.043 (4)* | |
H13B | −0.1350 (9) | 0.3943 (16) | −0.2781 (13) | 0.046 (4)* | |
H13C | −0.2115 (9) | 0.4033 (16) | −0.3742 (13) | 0.048 (4)* | |
H13A | −0.1610 (8) | 0.3016 (16) | −0.3807 (13) | 0.044 (4)* | |
H15C | −0.0874 (9) | 0.5523 (16) | 0.0104 (14) | 0.048 (5)* | |
H16C | 0.1074 (7) | 0.0998 (15) | −0.0635 (13) | 0.039 (4)* | |
H10B | 0.1197 (8) | 0.3351 (14) | 0.1849 (11) | 0.033 (4)* | |
H15B | −0.0607 (8) | 0.5762 (17) | 0.1354 (13) | 0.051 (5)* | |
H16B | 0.1651 (9) | 0.0324 (16) | 0.0529 (12) | 0.045 (4)* | |
H10A | 0.0662 (7) | 0.3796 (14) | 0.2119 (11) | 0.029 (4)* | |
H6 | −0.0088 (7) | 0.0894 (14) | −0.1260 (11) | 0.027 (3)* | |
H16A | 0.0867 (7) | −0.0216 (15) | −0.0184 (11) | 0.032 (4)* | |
H14B | −0.2889 (9) | 0.1962 (16) | −0.4113 (14) | 0.049 (4)* | |
H2 | −0.2618 (8) | 0.3299 (14) | −0.2456 (12) | 0.036 (4)* | |
H14A | −0.2314 (8) | 0.1021 (16) | −0.4013 (13) | 0.046 (4)* | |
H3 | −0.1779 (7) | 0.3663 (14) | −0.0630 (12) | 0.034 (4)* | |
H21 | 0.2319 (10) | 0.1540 (19) | 0.5044 (16) | 0.071 (6)* | |
H11B | 0.1105 (7) | 0.1106 (15) | 0.2426 (11) | 0.037 (4)* | |
H11A | 0.0669 (8) | 0.1733 (14) | 0.2818 (11) | 0.037 (4)* | |
H14C | −0.2578 (9) | 0.0818 (18) | −0.3218 (13) | 0.055 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C13 | 0.0360 (8) | 0.0343 (8) | 0.0309 (8) | −0.0002 (7) | 0.0185 (7) | 0.0030 (7) |
C15 | 0.0415 (9) | 0.0255 (7) | 0.0368 (8) | 0.0071 (6) | 0.0227 (7) | −0.0003 (6) |
O20 | 0.0253 (5) | 0.0259 (5) | 0.0261 (5) | −0.0027 (4) | 0.0096 (4) | 0.0019 (4) |
C16 | 0.0290 (8) | 0.0293 (8) | 0.0369 (8) | 0.0038 (6) | 0.0189 (7) | −0.0045 (6) |
O19 | 0.0224 (5) | 0.0316 (5) | 0.0309 (5) | 0.0049 (4) | 0.0118 (4) | −0.0041 (4) |
C10 | 0.0250 (7) | 0.0239 (7) | 0.0250 (7) | 0.0004 (5) | 0.0116 (6) | −0.0006 (5) |
C7 | 0.0220 (6) | 0.0213 (6) | 0.0264 (7) | 0.0020 (5) | 0.0119 (6) | 0.0018 (5) |
C8 | 0.0237 (7) | 0.0210 (6) | 0.0222 (7) | 0.0000 (5) | 0.0112 (6) | 0.0011 (5) |
C6 | 0.0268 (7) | 0.0217 (7) | 0.0263 (7) | 0.0012 (5) | 0.0139 (6) | −0.0018 (5) |
C1 | 0.0218 (6) | 0.0264 (7) | 0.0244 (7) | 0.0013 (5) | 0.0075 (6) | 0.0019 (5) |
C9 | 0.0272 (7) | 0.0205 (6) | 0.0233 (7) | 0.0013 (5) | 0.0158 (6) | 0.0016 (5) |
O18 | 0.0305 (5) | 0.0274 (5) | 0.0254 (5) | 0.0030 (4) | 0.0177 (4) | 0.0002 (4) |
C12 | 0.0236 (6) | 0.0259 (7) | 0.0247 (7) | 0.0020 (5) | 0.0149 (6) | 0.0013 (5) |
C5 | 0.0246 (7) | 0.0219 (6) | 0.0218 (6) | −0.0012 (5) | 0.0097 (6) | 0.0004 (5) |
C4 | 0.0226 (7) | 0.0221 (7) | 0.0249 (7) | 0.0000 (5) | 0.0127 (6) | 0.0032 (5) |
C2 | 0.0224 (7) | 0.0301 (7) | 0.0293 (7) | 0.0011 (6) | 0.0126 (6) | 0.0038 (6) |
O17 | 0.0242 (5) | 0.0265 (5) | 0.0240 (5) | 0.0021 (4) | 0.0064 (4) | −0.0027 (4) |
C3 | 0.0248 (7) | 0.0283 (7) | 0.0278 (7) | 0.0025 (5) | 0.0151 (6) | 0.0028 (6) |
C11 | 0.0236 (7) | 0.0260 (7) | 0.0249 (7) | −0.0021 (5) | 0.0115 (6) | −0.0005 (5) |
C14 | 0.0274 (8) | 0.0342 (8) | 0.0320 (8) | −0.0024 (6) | 0.0053 (7) | −0.0027 (7) |
O21 | 0.0317 (5) | 0.0276 (5) | 0.0242 (5) | −0.0041 (4) | 0.0086 (4) | 0.0043 (4) |
C13—C1 | 1.5202 (18) | C6—C5 | 1.3859 (18) |
C13—H13B | 0.982 (17) | C6—H6 | 0.974 (14) |
C13—H13C | 0.991 (17) | C1—O17 | 1.4664 (15) |
C13—H13A | 1.005 (17) | C1—C2 | 1.5089 (18) |
C15—O18 | 1.4365 (16) | C1—C14 | 1.5140 (19) |
C15—H15A | 1.024 (16) | C9—O18 | 1.3899 (14) |
C15—H15C | 0.976 (18) | C9—C4 | 1.4009 (17) |
C15—H15B | 1.016 (18) | C12—O21 | 1.3188 (15) |
O20—C12 | 1.2252 (15) | C12—C11 | 1.4965 (17) |
C16—O19 | 1.4338 (15) | C5—O17 | 1.3717 (15) |
C16—H16C | 1.018 (16) | C5—C4 | 1.3995 (17) |
C16—H16B | 1.011 (17) | C4—C3 | 1.4575 (17) |
C16—H16A | 0.985 (15) | C2—C3 | 1.3261 (19) |
O19—C7 | 1.3692 (15) | C2—H2 | 1.025 (16) |
C10—C8 | 1.5063 (17) | C3—H3 | 0.971 (15) |
C10—C11 | 1.5223 (18) | C11—H11B | 0.991 (15) |
C10—H10B | 0.996 (15) | C11—H11A | 0.978 (16) |
C10—H10A | 0.972 (14) | C14—H14B | 0.990 (18) |
C7—C6 | 1.3886 (18) | C14—H14A | 0.994 (17) |
C7—C8 | 1.4095 (17) | C14—H14C | 1.004 (18) |
C8—C9 | 1.3882 (17) | O21—H21 | 1.04 (2) |
C1—C13—H13B | 109.5 (9) | O17—C1—C13 | 107.84 (10) |
C1—C13—H13C | 110.9 (9) | C2—C1—C13 | 110.68 (11) |
H13B—C13—H13C | 107.5 (14) | C14—C1—C13 | 111.91 (12) |
C1—C13—H13A | 110.9 (9) | C8—C9—O18 | 118.70 (10) |
H13B—C13—H13A | 110.3 (13) | C8—C9—C4 | 123.13 (11) |
H13C—C13—H13A | 107.7 (13) | O18—C9—C4 | 118.12 (10) |
O18—C15—H15A | 110.4 (9) | C9—O18—C15 | 112.76 (9) |
O18—C15—H15C | 111.2 (10) | O20—C12—O21 | 122.90 (11) |
H15A—C15—H15C | 106.3 (13) | O20—C12—C11 | 123.42 (11) |
O18—C15—H15B | 107.2 (9) | O21—C12—C11 | 113.66 (11) |
H15A—C15—H15B | 109.1 (12) | O17—C5—C6 | 117.31 (11) |
H15C—C15—H15B | 112.7 (13) | O17—C5—C4 | 120.69 (11) |
O19—C16—H16C | 111.4 (8) | C6—C5—C4 | 121.83 (12) |
O19—C16—H16B | 105.1 (9) | C5—C4—C9 | 117.31 (11) |
H16C—C16—H16B | 112.4 (12) | C5—C4—C3 | 118.03 (11) |
O19—C16—H16A | 110.5 (8) | C9—C4—C3 | 124.54 (11) |
H16C—C16—H16A | 106.8 (12) | C3—C2—C1 | 121.39 (12) |
H16B—C16—H16A | 110.8 (13) | C3—C2—H2 | 122.5 (8) |
C7—O19—C16 | 117.86 (10) | C1—C2—H2 | 116.0 (8) |
C8—C10—C11 | 112.85 (11) | C5—O17—C1 | 117.27 (9) |
C8—C10—H10B | 109.9 (8) | C2—C3—C4 | 119.69 (12) |
C11—C10—H10B | 109.7 (8) | C2—C3—H3 | 123.0 (9) |
C8—C10—H10A | 108.7 (8) | C4—C3—H3 | 117.3 (9) |
C11—C10—H10A | 109.4 (8) | C12—C11—C10 | 113.18 (11) |
H10B—C10—H10A | 106.0 (11) | C12—C11—H11B | 106.2 (8) |
O19—C7—C6 | 123.74 (11) | C10—C11—H11B | 113.4 (8) |
O19—C7—C8 | 114.30 (11) | C12—C11—H11A | 107.1 (9) |
C6—C7—C8 | 121.95 (11) | C10—C11—H11A | 111.6 (9) |
C9—C8—C7 | 116.95 (11) | H11B—C11—H11A | 104.8 (12) |
C9—C8—C10 | 122.60 (11) | C1—C14—H14B | 112.4 (10) |
C7—C8—C10 | 120.45 (11) | C1—C14—H14A | 110.3 (9) |
C5—C6—C7 | 118.83 (12) | H14B—C14—H14A | 106.4 (13) |
C5—C6—H6 | 120.5 (8) | C1—C14—H14C | 108.7 (10) |
C7—C6—H6 | 120.6 (8) | H14B—C14—H14C | 110.1 (14) |
O17—C1—C2 | 110.29 (10) | H14A—C14—H14C | 108.9 (13) |
O17—C1—C14 | 104.40 (11) | C12—O21—H21 | 107.8 (11) |
C2—C1—C14 | 111.48 (11) | ||
C16—O19—C7—C6 | −2.23 (18) | O18—C9—C4—C5 | −176.57 (10) |
C16—O19—C7—C8 | 178.91 (11) | C8—C9—C4—C3 | 176.88 (11) |
O19—C7—C8—C9 | 178.85 (10) | O18—C9—C4—C3 | −0.69 (18) |
C6—C7—C8—C9 | −0.03 (18) | O17—C1—C2—C3 | 28.36 (16) |
O19—C7—C8—C10 | −0.03 (16) | C14—C1—C2—C3 | 143.85 (14) |
C6—C7—C8—C10 | −178.91 (11) | C13—C1—C2—C3 | −90.90 (15) |
C11—C10—C8—C9 | 107.22 (14) | C6—C5—O17—C1 | −154.61 (11) |
C11—C10—C8—C7 | −73.97 (15) | C4—C5—O17—C1 | 29.92 (16) |
O19—C7—C6—C5 | −178.64 (11) | C2—C1—O17—C5 | −41.33 (14) |
C8—C7—C6—C5 | 0.14 (19) | C14—C1—O17—C5 | −161.20 (11) |
C7—C8—C9—O18 | 177.00 (10) | C13—C1—O17—C5 | 79.63 (13) |
C10—C8—C9—O18 | −4.15 (17) | C1—C2—C3—C4 | −2.76 (19) |
C7—C8—C9—C4 | −0.56 (18) | C5—C4—C3—C2 | −12.07 (18) |
C10—C8—C9—C4 | 178.29 (11) | C9—C4—C3—C2 | 172.08 (12) |
C8—C9—O18—C15 | 95.58 (13) | O20—C12—C11—C10 | 0.79 (17) |
C4—C9—O18—C15 | −86.74 (14) | O21—C12—C11—C10 | −177.71 (10) |
C7—C6—C5—O17 | −175.07 (10) | C8—C10—C11—C12 | 171.40 (10) |
C7—C6—C5—C4 | 0.33 (19) | O17—C2—C3—C4 | 12.76 (13) |
O17—C5—C4—C9 | 174.38 (10) | C2—C3—C4—C5 | −12.07 (18) |
C6—C5—C4—C9 | −0.87 (18) | C3—C4—C5—C6 | −177.03 (11) |
O17—C5—C4—C3 | −1.78 (17) | C4—C5—C6—C7 | 0.33 (19) |
C6—C5—C4—C3 | −177.03 (11) | C5—C6—C7—C8 | 0.14 (19) |
C8—C9—C4—C5 | 1.00 (18) | C6—C7—C8—C9 | −0.03 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O21—H21···O20i | 1.04 (2) | 1.59 (2) | 2.6238 (12) | 171.1 (17) |
C16—H16B···O21ii | 1.011 (17) | 2.607 (15) | 2.9820 (16) | 101.8 (10) |
C15—H15A···CgBziii | 1.024 (16) | 2.814 (16) | 3.5534 (15) | 129.4 (11) |
C16—H16A···CgBziv | 0.985 (15) | 2.756 (15) | 3.6568 (15) | 152.2 (11) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) x, −y, z−1/2; (iii) −x, −y+1, −z; (iv) −x, −y, −z. |