Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021146/dn6014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021146/dn6014Isup2.hkl |
CCDC reference: 180540
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.002 Å
- R factor = 0.056
- wR factor = 0.133
- Data-to-parameter ratio = 24.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ O1[A] H2 O1[A] PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ O5[B] H2 O5[B] PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ O6[C] H4 O6[C] PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ O7[D] H4 O7[D] PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ O4[E] H5 O4[E] PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ O1[A] O2 O1[A] PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ O5[B] O2 O5[B] PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ O6[C] O4 O6[C] PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ O7[D] O4 O7[D] PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ O4[E] O5 O4[E] PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ O1[A] O2 H2 O1[A] PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ O5[B] O2 H2 O5[B] PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ O6[C] O4 H4 O6[C] PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ O7[D] O4 H4 O7[D] PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ O4[E] O5 H5 O4[E]
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
15 Alert Level C = Please check
erythro-(2,6-Dimethoxyphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)-1,3- propanediol was synthesized following the method described by Li et al. (2000). M.p. 390–391 K (from ethyl acetate).
H atoms were refined isotropically and were constrained to the ideal geometry using an appropriate riding model. For hydroxyl groups, the O—H distances (0.84 Å) and C–O–H angles (109.5°) were kept fixed, the torsion angle was chosen to maximize the electron density. For methyl groups, the C—H distances (0.98 Å) and C—C—H angles (109.5°) were kept fixed, while the torsion angles were allowed to refine with the starting position based on the threefold averaged circular Fourier synthesis.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2001); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.
C19H24O8 | Dx = 1.344 Mg m−3 |
Mr = 380.38 | Melting point: 490–491 K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.9064 (5) Å | Cell parameters from 6618 reflections |
b = 15.6222 (6) Å | θ = 2.1–33.0° |
c = 9.9140 (4) Å | µ = 0.11 mm−1 |
β = 109.837 (1)° | T = 183 K |
V = 1880.31 (13) Å3 | Plate, colorless |
Z = 4 | 0.24 × 0.12 × 0.05 mm |
F(000) = 808 |
Siemens SMART CCD diffractometer | 6775 independent reflections |
Radiation source: fine-focus sealed tube | 4740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 33.0°, θmin = 2.1° |
Absorption correction: empirical (using intensity measurements) (SADABS: Sheldrick, 2001) | h = −19→19 |
Tmin = 0.975, Tmax = 0.995 | k = −23→23 |
30831 measured reflections | l = −14→15 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.7831P] where P = (Fo2 + 2Fc2)/3 |
6775 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C19H24O8 | V = 1880.31 (13) Å3 |
Mr = 380.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.9064 (5) Å | µ = 0.11 mm−1 |
b = 15.6222 (6) Å | T = 183 K |
c = 9.9140 (4) Å | 0.24 × 0.12 × 0.05 mm |
β = 109.837 (1)° |
Siemens SMART CCD diffractometer | 6775 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS: Sheldrick, 2001) | 4740 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.995 | Rint = 0.047 |
30831 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.34 e Å−3 |
6775 reflections | Δρmin = −0.24 e Å−3 |
275 parameters |
Experimental. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped with a Siemens LT-2 A low temperature device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 30 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8192 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2001) based on the method of Blessing (1995). |
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 | ||
O1 | 0.54877 (8) | 0.63827 (7) | 0.06729 (12) | 0.0330 (2) | |
O2 | 0.40664 (8) | 0.57723 (7) | 0.19306 (12) | 0.0345 (2) | |
H2 | 0.4033 | 0.6232 | 0.1477 | 0.058 (6)* | |
O3 | 0.45442 (8) | 0.44457 (7) | 0.36346 (12) | 0.0317 (2) | |
O4 | 0.83034 (8) | 0.34278 (7) | 0.40170 (11) | 0.0294 (2) | |
H4 | 0.8897 | 0.3168 | 0.4136 | 0.052 (6)* | |
O5 | 0.67744 (8) | 0.27491 (6) | −0.04899 (11) | 0.0281 (2) | |
H5 | 0.7313 | 0.2510 | −0.0628 | 0.060 (6)* | |
O6 | 0.89866 (7) | 0.30589 (6) | 0.16481 (10) | 0.02377 (19) | |
O7 | 1.05699 (8) | 0.32620 (7) | 0.41792 (12) | 0.0364 (2) | |
O8 | 0.92194 (9) | 0.36156 (7) | −0.07989 (12) | 0.0362 (2) | |
C1 | 0.70832 (10) | 0.45476 (8) | 0.27173 (14) | 0.0226 (2) | |
C2 | 0.68233 (10) | 0.52561 (8) | 0.18031 (15) | 0.0242 (3) | |
H2A | 0.7327 | 0.5448 | 0.1358 | 0.030 (4)* | |
C3 | 0.58251 (11) | 0.56810 (8) | 0.15436 (14) | 0.0244 (3) | |
C4 | 0.50696 (10) | 0.54012 (9) | 0.21778 (15) | 0.0253 (3) | |
C5 | 0.53411 (11) | 0.46956 (9) | 0.30919 (15) | 0.0253 (3) | |
C6 | 0.63431 (10) | 0.42749 (8) | 0.33715 (15) | 0.0248 (3) | |
H6 | 0.6522 | 0.3801 | 0.4010 | 0.029 (4)* | |
C7 | 0.61448 (13) | 0.66333 (10) | −0.01568 (18) | 0.0350 (3) | |
H7A | 0.6858 | 0.6844 | 0.0481 | 0.037 (5)* | |
H7B | 0.5769 | 0.7089 | −0.0823 | 0.039 (5)* | |
H7C | 0.6261 | 0.6140 | −0.0700 | 0.043 (5)* | |
C8 | 0.47904 (13) | 0.37127 (10) | 0.45494 (19) | 0.0382 (4) | |
H8A | 0.4897 | 0.3214 | 0.4011 | 0.036 (5)* | |
H8B | 0.4178 | 0.3603 | 0.4900 | 0.057 (6)* | |
H8C | 0.5464 | 0.3818 | 0.5365 | 0.046 (5)* | |
C9 | 0.81179 (10) | 0.40376 (8) | 0.28820 (14) | 0.0233 (2) | |
H9 | 0.8759 | 0.4439 | 0.3129 | 0.023 (4)* | |
C10 | 0.80185 (10) | 0.35801 (8) | 0.14716 (14) | 0.0212 (2) | |
H10 | 0.7940 | 0.4015 | 0.0703 | 0.018 (3)* | |
C11 | 0.70577 (10) | 0.29601 (9) | 0.09901 (14) | 0.0243 (3) | |
H11A | 0.7253 | 0.2431 | 0.1570 | 0.028 (4)* | |
H11B | 0.6412 | 0.3220 | 0.1157 | 0.031 (4)* | |
C12 | 0.99308 (10) | 0.34949 (8) | 0.16955 (16) | 0.0267 (3) | |
C13 | 1.07755 (11) | 0.35936 (9) | 0.30110 (17) | 0.0311 (3) | |
C14 | 1.17538 (12) | 0.40017 (11) | 0.3073 (2) | 0.0430 (4) | |
H14 | 1.2326 | 0.4082 | 0.3966 | 0.048 (5)* | |
C15 | 1.18779 (13) | 0.42878 (12) | 0.1817 (2) | 0.0483 (5) | |
H15 | 1.2539 | 0.4572 | 0.1860 | 0.058 (6)* | |
C16 | 1.10646 (14) | 0.41698 (11) | 0.0503 (2) | 0.0423 (4) | |
H16 | 1.1174 | 0.4360 | −0.0349 | 0.050 (6)* | |
C17 | 1.00784 (12) | 0.37690 (9) | 0.04312 (17) | 0.0313 (3) | |
C18 | 1.14074 (15) | 0.33374 (14) | 0.5546 (2) | 0.0509 (5) | |
H18A | 1.2079 | 0.3055 | 0.5523 | 0.074 (7)* | |
H18B | 1.1160 | 0.3065 | 0.6274 | 0.074 (8)* | |
H18C | 1.1560 | 0.3944 | 0.5782 | 0.067 (7)* | |
C19 | 0.93714 (19) | 0.38356 (11) | −0.2123 (2) | 0.0476 (5) | |
H19A | 0.9569 | 0.4442 | −0.2108 | 0.050 (5)* | |
H19B | 0.8686 | 0.3730 | −0.2922 | 0.055 (6)* | |
H19C | 0.9963 | 0.3485 | −0.2245 | 0.062 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0306 (5) | 0.0316 (5) | 0.0434 (6) | 0.0078 (4) | 0.0212 (5) | 0.0123 (4) |
O2 | 0.0243 (5) | 0.0377 (6) | 0.0470 (7) | 0.0112 (4) | 0.0192 (5) | 0.0151 (5) |
O3 | 0.0247 (5) | 0.0343 (5) | 0.0436 (6) | 0.0061 (4) | 0.0212 (4) | 0.0122 (4) |
O4 | 0.0218 (5) | 0.0389 (6) | 0.0289 (5) | 0.0080 (4) | 0.0104 (4) | 0.0073 (4) |
O5 | 0.0219 (4) | 0.0298 (5) | 0.0322 (5) | 0.0001 (4) | 0.0086 (4) | −0.0058 (4) |
O6 | 0.0168 (4) | 0.0214 (4) | 0.0363 (5) | −0.0008 (3) | 0.0130 (4) | −0.0007 (4) |
O7 | 0.0225 (5) | 0.0444 (6) | 0.0390 (6) | −0.0016 (4) | 0.0060 (4) | −0.0017 (5) |
O8 | 0.0414 (6) | 0.0373 (6) | 0.0372 (6) | −0.0066 (5) | 0.0228 (5) | −0.0021 (5) |
C1 | 0.0178 (5) | 0.0251 (6) | 0.0256 (6) | 0.0000 (4) | 0.0082 (5) | −0.0029 (5) |
C2 | 0.0197 (5) | 0.0251 (6) | 0.0305 (7) | −0.0010 (5) | 0.0121 (5) | −0.0008 (5) |
C3 | 0.0230 (6) | 0.0237 (6) | 0.0283 (7) | 0.0015 (5) | 0.0110 (5) | 0.0019 (5) |
C4 | 0.0199 (6) | 0.0275 (6) | 0.0307 (7) | 0.0036 (5) | 0.0115 (5) | 0.0021 (5) |
C5 | 0.0217 (6) | 0.0279 (6) | 0.0304 (7) | 0.0007 (5) | 0.0139 (5) | 0.0017 (5) |
C6 | 0.0218 (6) | 0.0257 (6) | 0.0286 (7) | 0.0028 (5) | 0.0107 (5) | 0.0029 (5) |
C7 | 0.0372 (8) | 0.0339 (7) | 0.0413 (9) | 0.0034 (6) | 0.0230 (7) | 0.0087 (6) |
C8 | 0.0356 (8) | 0.0379 (8) | 0.0519 (10) | 0.0099 (6) | 0.0289 (8) | 0.0164 (7) |
C9 | 0.0173 (5) | 0.0262 (6) | 0.0271 (6) | 0.0004 (4) | 0.0086 (5) | −0.0001 (5) |
C10 | 0.0158 (5) | 0.0223 (5) | 0.0274 (6) | 0.0007 (4) | 0.0097 (5) | 0.0007 (5) |
C11 | 0.0180 (5) | 0.0277 (6) | 0.0285 (7) | −0.0035 (5) | 0.0097 (5) | −0.0011 (5) |
C12 | 0.0179 (5) | 0.0231 (6) | 0.0436 (8) | −0.0010 (4) | 0.0164 (6) | −0.0031 (5) |
C13 | 0.0193 (6) | 0.0301 (7) | 0.0459 (9) | −0.0004 (5) | 0.0136 (6) | −0.0044 (6) |
C14 | 0.0187 (6) | 0.0431 (9) | 0.0659 (12) | −0.0052 (6) | 0.0126 (7) | −0.0069 (8) |
C15 | 0.0248 (7) | 0.0441 (9) | 0.0845 (14) | −0.0081 (7) | 0.0296 (9) | −0.0044 (9) |
C16 | 0.0359 (8) | 0.0385 (8) | 0.0676 (12) | −0.0045 (6) | 0.0373 (9) | −0.0011 (8) |
C17 | 0.0278 (7) | 0.0273 (7) | 0.0470 (9) | −0.0012 (5) | 0.0233 (6) | −0.0047 (6) |
C18 | 0.0358 (9) | 0.0674 (13) | 0.0417 (10) | −0.0054 (8) | 0.0029 (8) | −0.0111 (9) |
C19 | 0.0769 (13) | 0.0346 (8) | 0.0451 (10) | −0.0089 (8) | 0.0387 (10) | −0.0033 (7) |
O1—C3 | 1.3717 (16) | C7—H7B | 0.9800 |
O1—C7 | 1.4222 (17) | C7—H7C | 0.9800 |
O2—C4 | 1.3628 (15) | C8—H8A | 0.9800 |
O2—H2 | 0.8400 | C8—H8B | 0.9800 |
O3—C5 | 1.3694 (15) | C8—H8C | 0.9800 |
O3—C8 | 1.4281 (18) | C9—C10 | 1.5364 (18) |
O4—C9 | 1.4312 (16) | C9—H9 | 1.0000 |
O4—H4 | 0.8400 | C10—C11 | 1.5172 (17) |
O5—C11 | 1.4252 (16) | C10—H10 | 1.0000 |
O5—H5 | 0.8400 | C11—H11A | 0.9900 |
O6—C12 | 1.3829 (15) | C11—H11B | 0.9900 |
O6—C10 | 1.4514 (14) | C12—C13 | 1.396 (2) |
O7—C13 | 1.3742 (19) | C12—C17 | 1.398 (2) |
O7—C18 | 1.423 (2) | C13—C14 | 1.397 (2) |
O8—C17 | 1.3624 (19) | C14—C15 | 1.382 (3) |
O8—C19 | 1.4334 (19) | C14—H14 | 0.9500 |
C1—C6 | 1.3911 (17) | C15—C16 | 1.380 (3) |
C1—C2 | 1.3973 (19) | C15—H15 | 0.9500 |
C1—C9 | 1.5156 (17) | C16—C17 | 1.398 (2) |
C2—C3 | 1.3935 (18) | C16—H16 | 0.9500 |
C2—H2A | 0.9500 | C18—H18A | 0.9800 |
C3—C4 | 1.3975 (18) | C18—H18B | 0.9800 |
C4—C5 | 1.3942 (19) | C18—H18C | 0.9800 |
C5—C6 | 1.3920 (18) | C19—H19A | 0.9800 |
C6—H6 | 0.9500 | C19—H19B | 0.9800 |
C7—H7A | 0.9800 | C19—H19C | 0.9800 |
C3—O1—C7 | 117.37 (11) | C10—C9—H9 | 108.8 |
C4—O2—H2 | 109.5 | O6—C10—C11 | 104.95 (10) |
C5—O3—C8 | 116.31 (10) | O6—C10—C9 | 110.40 (10) |
C9—O4—H4 | 109.5 | C11—C10—C9 | 112.97 (10) |
C11—O5—H5 | 109.5 | O6—C10—H10 | 109.5 |
C12—O6—C10 | 116.14 (9) | C11—C10—H10 | 109.5 |
C13—O7—C18 | 118.03 (13) | C9—C10—H10 | 109.5 |
C17—O8—C19 | 117.06 (13) | O5—C11—C10 | 111.61 (10) |
C6—C1—C2 | 119.56 (11) | O5—C11—H11A | 109.3 |
C6—C1—C9 | 120.54 (12) | C10—C11—H11A | 109.3 |
C2—C1—C9 | 119.67 (11) | O5—C11—H11B | 109.3 |
C3—C2—C1 | 120.03 (12) | C10—C11—H11B | 109.3 |
C3—C2—H2A | 120.0 | H11A—C11—H11B | 108.0 |
C1—C2—H2A | 120.0 | O6—C12—C13 | 119.08 (13) |
O1—C3—C2 | 124.96 (12) | O6—C12—C17 | 120.48 (13) |
O1—C3—C4 | 114.34 (11) | C13—C12—C17 | 120.22 (12) |
C2—C3—C4 | 120.70 (12) | O7—C13—C14 | 124.42 (15) |
O2—C4—C3 | 123.46 (12) | O7—C13—C12 | 115.65 (12) |
O2—C4—C5 | 117.85 (11) | C14—C13—C12 | 119.93 (15) |
C3—C4—C5 | 118.68 (12) | C15—C14—C13 | 119.17 (16) |
O3—C5—C6 | 123.92 (12) | C15—C14—H14 | 120.4 |
O3—C5—C4 | 115.09 (11) | C13—C14—H14 | 120.4 |
C6—C5—C4 | 120.95 (12) | C14—C15—C16 | 121.56 (14) |
C5—C6—C1 | 120.07 (12) | C14—C15—H15 | 119.2 |
C5—C6—H6 | 120.0 | C16—C15—H15 | 119.2 |
C1—C6—H6 | 120.0 | C17—C16—C15 | 119.70 (16) |
O1—C7—H7A | 109.5 | C17—C16—H16 | 120.2 |
O1—C7—H7B | 109.5 | C15—C16—H16 | 120.2 |
H7A—C7—H7B | 109.5 | O8—C17—C12 | 115.58 (12) |
O1—C7—H7C | 109.5 | O8—C17—C16 | 125.06 (15) |
H7A—C7—H7C | 109.5 | C12—C17—C16 | 119.36 (15) |
H7B—C7—H7C | 109.5 | O7—C18—H18A | 109.5 |
O3—C8—H8A | 109.5 | O7—C18—H18B | 109.5 |
O3—C8—H8B | 109.5 | H18A—C18—H18B | 109.5 |
H8A—C8—H8B | 109.5 | O7—C18—H18C | 109.5 |
O3—C8—H8C | 109.5 | H18A—C18—H18C | 109.5 |
H8A—C8—H8C | 109.5 | H18B—C18—H18C | 109.5 |
H8B—C8—H8C | 109.5 | O8—C19—H19A | 109.5 |
O4—C9—C1 | 109.92 (10) | O8—C19—H19B | 109.5 |
O4—C9—C10 | 110.24 (10) | H19A—C19—H19B | 109.5 |
C1—C9—C10 | 110.37 (10) | O8—C19—H19C | 109.5 |
O4—C9—H9 | 108.8 | H19A—C19—H19C | 109.5 |
C1—C9—H9 | 108.8 | H19B—C19—H19C | 109.5 |
C6—C1—C2—C3 | −0.5 (2) | O4—C9—C10—O6 | −55.65 (12) |
C9—C1—C2—C3 | 174.11 (12) | C1—C9—C10—O6 | −177.27 (10) |
C7—O1—C3—C2 | 7.8 (2) | O4—C9—C10—C11 | 61.52 (13) |
C7—O1—C3—C4 | −171.80 (13) | C1—C9—C10—C11 | −60.10 (14) |
C1—C2—C3—O1 | 179.75 (13) | O6—C10—C11—O5 | −77.72 (13) |
C1—C2—C3—C4 | −0.7 (2) | C9—C10—C11—O5 | 161.94 (10) |
O1—C3—C4—O2 | 1.8 (2) | C10—O6—C12—C13 | 105.07 (14) |
C2—C3—C4—O2 | −177.84 (13) | C10—O6—C12—C17 | −80.35 (15) |
O1—C3—C4—C5 | −179.48 (12) | C18—O7—C13—C14 | 0.0 (2) |
C2—C3—C4—C5 | 0.9 (2) | C18—O7—C13—C12 | 179.40 (14) |
C8—O3—C5—C6 | 0.7 (2) | O6—C12—C13—O7 | −2.05 (18) |
C8—O3—C5—C4 | 178.66 (13) | C17—C12—C13—O7 | −176.63 (12) |
O2—C4—C5—O3 | 0.73 (19) | O6—C12—C13—C14 | 177.42 (13) |
C3—C4—C5—O3 | −178.07 (12) | C17—C12—C13—C14 | 2.8 (2) |
O2—C4—C5—C6 | 178.79 (13) | O7—C13—C14—C15 | 178.14 (15) |
C3—C4—C5—C6 | 0.0 (2) | C12—C13—C14—C15 | −1.3 (2) |
O3—C5—C6—C1 | 176.78 (13) | C13—C14—C15—C16 | −0.9 (3) |
C4—C5—C6—C1 | −1.1 (2) | C14—C15—C16—C17 | 1.4 (3) |
C2—C1—C6—C5 | 1.3 (2) | C19—O8—C17—C12 | −175.89 (13) |
C9—C1—C6—C5 | −173.20 (12) | C19—O8—C17—C16 | 4.1 (2) |
C6—C1—C9—O4 | −14.03 (17) | O6—C12—C17—O8 | 3.22 (18) |
C2—C1—C9—O4 | 171.45 (11) | C13—C12—C17—O8 | 177.73 (12) |
C6—C1—C9—C10 | 107.78 (14) | O6—C12—C17—C16 | −176.75 (12) |
C2—C1—C9—C10 | −66.74 (15) | C13—C12—C17—C16 | −2.2 (2) |
C12—O6—C10—C11 | 162.71 (11) | C15—C16—C17—O8 | −179.85 (15) |
C12—O6—C10—C9 | −75.26 (13) | C15—C16—C17—C12 | 0.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1[a] | 0.84 | 2.29 | 2.7168 (14) | 112 |
O2—H2···O5[b]i | 0.84 | 1.97 | 2.7388 (14) | 152 |
O4—H4···O6[c] | 0.84 | 2.51 | 2.8339 (13) | 104 |
O4—H4···O7[d] | 0.84 | 2.15 | 2.8863 (14) | 146 |
O5—H5···O4[e]ii | 0.84 | 2.05 | 2.8580 (14) | 161 |
C6—H6···O4 | 0.95 | 2.37 | 2.7319 (16) | 102 |
C6—H6···O5iii | 0.95 | 2.47 | 3.3401 (16) | 152 |
C11—H11B···O1i | 0.99 | 2.58 | 3.2998 (16) | 129 |
C15—H15···O3iv | 0.95 | 2.60 | 3.308 (2) | 132 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C19H24O8 |
Mr | 380.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 183 |
a, b, c (Å) | 12.9064 (5), 15.6222 (6), 9.9140 (4) |
β (°) | 109.837 (1) |
V (Å3) | 1880.31 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.24 × 0.12 × 0.05 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS: Sheldrick, 2001) |
Tmin, Tmax | 0.975, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30831, 6775, 4740 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.767 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.133, 1.04 |
No. of reflections | 6775 |
No. of parameters | 275 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.24 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT and SADABS (Sheldrick, 2001), SHELXTL (Bruker, 1997), SHELXTL, DIAMOND (Brandenburg, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1[a] | 0.84 | 2.29 | 2.7168 (14) | 112.0 |
O2—H2···O5[b]i | 0.84 | 1.97 | 2.7388 (14) | 151.5 |
O4—H4···O6[c] | 0.84 | 2.51 | 2.8339 (13) | 103.8 |
O4—H4···O7[d] | 0.84 | 2.15 | 2.8863 (14) | 146.3 |
O5—H5···O4[e]ii | 0.84 | 2.05 | 2.8580 (14) | 160.7 |
C6—H6···O4 | 0.95 | 2.37 | 2.7319 (16) | 102.1 |
C6—H6···O5iii | 0.95 | 2.47 | 3.3401 (16) | 152.0 |
C11—H11B···O1i | 0.99 | 2.58 | 3.2998 (16) | 129.3 |
C15—H15···O3iv | 0.95 | 2.60 | 3.308 (2) | 131.9 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x+1, y, z. |
Crystal structures of erythro forms (1) and (2) of model compounds, representative of structural elements in lignin of the syringylglycerol β-syringyl ether type, have been described previously (Stomberg & Lundquist, 1989; Langer & Lundquist, 2001). The conformations of the compounds differed considerably. The torsion angle between the 1-aryl and the 2-aryloxy groups was for instance -71.0 (4)° in (1) and 178.58 (7)° in (2). The conformational differences were attributed to the different hydrogen-bonding patterns (Langer & Lundquist, 2001). To obtain a better basis for judging which factors govern the conformation of syringylglycerol β-syringyl ethers we have now determined the crystal structure of a third model compound representative of such ethers, erythro-2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)-1,3- propanediol, (3). This compound adopts a conformation in which the bulky aromatic groups are distant from each other. The torsion angle C9–C10–O6–C12 is -75.26 (13)° and the torsion angle C1–C9–C10–O6 is -177.27 (10)°. This leads to a C1—C12 distance of 4.4458 (17) Å. Corresponding data for (2) are -89.24 (9)°, 178.58 (7)° and 4.5030 (13) Å. The angle between the aromatic ring planes is 57.27 (5)° in (3) and 76.00 (3)° in (2). It is obvious that (2) and (3) adopt similar conformations. Nevertheless, the hydrogen-bonding patterns of (2) and (3) are different.
Both structures exhibit intramolecular hydrogen bonds of approximately the same strength, but in (2), they are formed by the hydroxyl H atom in the methylol group and the O atoms in a methoxy group and the phenoxy group (Langer & Lundquist, 2001), while in (3), they are formed by H(O4) and the atoms O6 and O7 (Fig. 1 and Table 1). The phenolic H(O2) atom, which is lacking in (2), forms an intramolecular hydrogen bond with O1 as acceptor. H(O2) also takes part in intermolecular hydrogen bonds. Assignment of the hydrogen-bond descriptors using program PLUTO (Motherwell et al., 1999) in terms of the graph-set theory (Bernstein et al., 1995) has been carried out. For this purpose, we use symbols of type Xa,d(n), where X is the pattern descriptor, a is the number of acceptors, d is the number of donors and n is the number of atoms comprising the pattern. For (3), there are on the first-level of intermolecular contacts a chain C1,1(6) formed by hydrogen bonds of type [e] (Fig. 2 and Table 1) and a ring R2,2(20), formed by hydrogen bonds of type [b] (Fig. 3). On the second-level of graph-set descriptors, chains C2,2(10) and C2,2(16) were identified, both formed by hydrogen bonds of [b] and [e] type. The structure of (2) exhibits (apart from intramolecular contacts) just one first-level descriptor, a chain C1,1(6) with the benzylic oxygen as donor and the oxygen in the methylol groups as acceptor (Langer & Lundquist, 2001).