Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057741/su2020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057741/su2020Isup2.hkl |
CCDC reference: 672976
Key indicators
- Single-crystal X-ray study
- T = 161 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.082
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.36 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A .. O1 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H19B .. O3 .. 2.64 Ang. PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGB PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGB PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGA PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CGA
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field. REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 70.01 From the CIF: _reflns_number_total 3429 Count of symmetry unique reflns 1913 Completeness (_total/calc) 179.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1516 Fraction of Friedel pairs measured 0.792 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The crystal structure of the title compound, determined at room temperature, was previously reported by Noe et al. (1994). A more precise determination at 161 K is reported here. An isomorphous crystal structure has been reported by Bats et al. (2007) and the structure of a closely related molecule by Bats et al. (2001). For the libration correction, see Farrugia (1999).
Compound (I) was prepared as described by Noe et al. (1994). Thin plates were obtained by crystallization from chloroform-hexane (1:1) at low temperature.
The H atoms were located in a difference Fourier map and were refined as riding with C(sp2)—H = 0.95 Å, Csecondary—H = 0.99 Å and with Uiso(H) = 1.2Ueq(C). Friedel opposites were not merged. The absolute structure was determined from the anomalous scattering contribution of the O atoms, using 1519 Friedel pairs. The thermal motion analysis was performed with the WinGX program package (Farrugia, 1999).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C19H24O6 | F(000) = 744 |
Mr = 348.38 | Dx = 1.276 Mg m−3 |
Monoclinic, C2 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: C 2y | Cell parameters from 25 reflections |
a = 40.733 (9) Å | θ = 39–61° |
b = 5.431 (1) Å | µ = 0.78 mm−1 |
c = 8.266 (3) Å | T = 161 K |
β = 97.34 (2)° | Plate, colourless |
V = 1813.6 (8) Å3 | 0.55 × 0.50 × 0.10 mm |
Z = 4 |
Enraf–Nonius CAD4 diffractometer | 3311 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 70.0°, θmin = 2.2° |
ω scans | h = −49→48 |
Absorption correction: numerical using eight faces (SHELXTL; Sheldrick, 1996) | k = −6→6 |
Tmin = 0.690, Tmax = 0.933 | l = 0→10 |
3681 measured reflections | 3 standard reflections every 92 min |
3429 independent reflections | intensity decay: <1% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.46P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max = 0.002 |
S = 1.10 | Δρmax = 0.13 e Å−3 |
3429 reflections | Δρmin = −0.12 e Å−3 |
228 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.00125 (12) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1519 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.23 (15) |
C19H24O6 | V = 1813.6 (8) Å3 |
Mr = 348.38 | Z = 4 |
Monoclinic, C2 | Cu Kα radiation |
a = 40.733 (9) Å | µ = 0.78 mm−1 |
b = 5.431 (1) Å | T = 161 K |
c = 8.266 (3) Å | 0.55 × 0.50 × 0.10 mm |
β = 97.34 (2)° |
Enraf–Nonius CAD4 diffractometer | 3311 reflections with I > 2σ(I) |
Absorption correction: numerical using eight faces (SHELXTL; Sheldrick, 1996) | Rint = 0.028 |
Tmin = 0.690, Tmax = 0.933 | 3 standard reflections every 92 min |
3681 measured reflections | intensity decay: <1% |
3429 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.082 | Δρmax = 0.13 e Å−3 |
S = 1.10 | Δρmin = −0.12 e Å−3 |
3429 reflections | Absolute structure: Flack (1983), with 1519 Friedel pairs |
228 parameters | Absolute structure parameter: 0.23 (15) |
1 restraint |
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 | 0.41078 (2) | 0.51161 (19) | 0.28403 (11) | 0.0377 (2) | |
O2 | 0.43216 (2) | 0.4939 (2) | 0.03376 (10) | 0.0345 (2) | |
O3 | 0.48919 (2) | 0.5043 (2) | 0.12547 (10) | 0.0335 (2) | |
O4 | 0.39454 (2) | 0.04835 (18) | 0.62151 (10) | 0.0344 (2) | |
O5 | 0.45158 (2) | 0.01186 (19) | 0.70716 (10) | 0.0338 (2) | |
O6 | 0.47152 (2) | −0.0039 (2) | 0.45254 (10) | 0.0346 (2) | |
C1 | 0.35059 (3) | 0.4797 (3) | 0.20153 (15) | 0.0334 (3) | |
C2 | 0.34789 (3) | 0.2676 (3) | 0.29233 (16) | 0.0328 (3) | |
H2 | 0.3660 | 0.2173 | 0.3689 | 0.039* | |
C3 | 0.31920 (3) | 0.1275 (3) | 0.27349 (19) | 0.0439 (4) | |
H3 | 0.3179 | −0.0174 | 0.3367 | 0.053* | |
C4 | 0.29282 (4) | 0.1978 (4) | 0.1640 (2) | 0.0590 (5) | |
H4 | 0.2731 | 0.1024 | 0.1511 | 0.071* | |
C5 | 0.29506 (4) | 0.4070 (4) | 0.0732 (2) | 0.0658 (6) | |
H5 | 0.2767 | 0.4564 | −0.0023 | 0.079* | |
C6 | 0.32371 (4) | 0.5474 (4) | 0.08976 (18) | 0.0513 (4) | |
H6 | 0.3250 | 0.6903 | 0.0245 | 0.062* | |
C7 | 0.38097 (4) | 0.6406 (3) | 0.2291 (2) | 0.0441 (4) | |
H7A | 0.3837 | 0.7256 | 0.1257 | 0.053* | |
H7B | 0.3774 | 0.7683 | 0.3105 | 0.053* | |
C8 | 0.42210 (3) | 0.3591 (3) | 0.16613 (16) | 0.0337 (3) | |
H8A | 0.4042 | 0.2436 | 0.1239 | 0.040* | |
H8B | 0.4410 | 0.2604 | 0.2179 | 0.040* | |
C9 | 0.46032 (3) | 0.6437 (3) | 0.07662 (16) | 0.0347 (3) | |
H9A | 0.4640 | 0.7473 | −0.0180 | 0.042* | |
H9B | 0.4562 | 0.7547 | 0.1668 | 0.042* | |
C10 | 0.5000 | 0.3592 (4) | 0.0000 | 0.0323 (4) | |
H10 | 0.5184 | 0.2519 | 0.0475 | 0.039* | |
C11 | 0.34710 (3) | −0.1303 (3) | 0.71490 (17) | 0.0360 (3) | |
C12 | 0.33846 (4) | −0.3416 (3) | 0.62612 (18) | 0.0411 (3) | |
H12 | 0.3553 | −0.4490 | 0.5981 | 0.049* | |
C13 | 0.30536 (4) | −0.3979 (3) | 0.57764 (19) | 0.0445 (4) | |
H13 | 0.2996 | −0.5416 | 0.5148 | 0.053* | |
C14 | 0.28097 (4) | −0.2455 (3) | 0.6206 (2) | 0.0446 (4) | |
H14 | 0.2584 | −0.2843 | 0.5875 | 0.054* | |
C15 | 0.28913 (4) | −0.0370 (3) | 0.71130 (19) | 0.0463 (4) | |
H15 | 0.2722 | 0.0662 | 0.7426 | 0.056* | |
C16 | 0.32216 (4) | 0.0226 (3) | 0.75710 (18) | 0.0409 (3) | |
H16 | 0.3278 | 0.1687 | 0.8176 | 0.049* | |
C17 | 0.38279 (4) | −0.0641 (3) | 0.76078 (17) | 0.0443 (4) | |
H17A | 0.3851 | 0.0520 | 0.8539 | 0.053* | |
H17B | 0.3959 | −0.2136 | 0.7934 | 0.053* | |
C18 | 0.42479 (3) | 0.1719 (3) | 0.65835 (16) | 0.0341 (3) | |
H18A | 0.4229 | 0.2918 | 0.7469 | 0.041* | |
H18B | 0.4295 | 0.2653 | 0.5611 | 0.041* | |
C19 | 0.46035 (3) | −0.1411 (3) | 0.58093 (17) | 0.0351 (3) | |
H19A | 0.4409 | −0.2407 | 0.5366 | 0.042* | |
H19B | 0.4781 | −0.2557 | 0.6266 | 0.042* | |
C20 | 0.5000 | 0.1404 (4) | 0.5000 | 0.0335 (4) | |
H20 | 0.4959 | 0.2478 | 0.5921 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0374 (5) | 0.0430 (5) | 0.0336 (5) | −0.0069 (5) | 0.0086 (4) | −0.0066 (5) |
O2 | 0.0294 (4) | 0.0461 (6) | 0.0278 (4) | 0.0032 (4) | 0.0029 (3) | −0.0015 (4) |
O3 | 0.0292 (4) | 0.0439 (5) | 0.0270 (4) | −0.0025 (4) | 0.0019 (3) | −0.0004 (4) |
O4 | 0.0287 (4) | 0.0461 (6) | 0.0280 (4) | −0.0014 (4) | 0.0025 (3) | 0.0040 (4) |
O5 | 0.0301 (4) | 0.0414 (5) | 0.0286 (4) | −0.0020 (4) | −0.0015 (3) | 0.0011 (4) |
O6 | 0.0320 (5) | 0.0424 (5) | 0.0285 (4) | 0.0012 (4) | 0.0000 (3) | −0.0009 (4) |
C1 | 0.0348 (6) | 0.0359 (7) | 0.0312 (6) | 0.0089 (6) | 0.0110 (5) | −0.0002 (6) |
C2 | 0.0293 (6) | 0.0344 (7) | 0.0346 (7) | 0.0019 (5) | 0.0036 (5) | −0.0003 (6) |
C3 | 0.0391 (7) | 0.0485 (8) | 0.0461 (8) | −0.0071 (7) | 0.0131 (6) | −0.0122 (7) |
C4 | 0.0305 (8) | 0.0827 (14) | 0.0630 (11) | −0.0010 (8) | 0.0033 (7) | −0.0340 (11) |
C5 | 0.0425 (9) | 0.1012 (17) | 0.0484 (10) | 0.0295 (10) | −0.0145 (7) | −0.0238 (10) |
C6 | 0.0613 (10) | 0.0583 (10) | 0.0336 (7) | 0.0280 (8) | 0.0039 (7) | 0.0018 (7) |
C7 | 0.0484 (8) | 0.0314 (7) | 0.0570 (9) | 0.0029 (7) | 0.0238 (7) | 0.0013 (7) |
C8 | 0.0290 (6) | 0.0370 (7) | 0.0349 (7) | 0.0005 (6) | 0.0040 (5) | −0.0006 (6) |
C9 | 0.0349 (7) | 0.0350 (7) | 0.0351 (7) | 0.0010 (6) | 0.0083 (5) | 0.0014 (6) |
C10 | 0.0275 (8) | 0.0358 (10) | 0.0330 (9) | 0.000 | 0.0017 (7) | 0.000 |
C11 | 0.0363 (7) | 0.0425 (7) | 0.0304 (7) | −0.0006 (6) | 0.0088 (5) | 0.0070 (6) |
C12 | 0.0398 (7) | 0.0411 (8) | 0.0441 (8) | 0.0051 (7) | 0.0114 (6) | −0.0011 (7) |
C13 | 0.0477 (8) | 0.0374 (8) | 0.0492 (8) | −0.0047 (6) | 0.0095 (6) | −0.0039 (7) |
C14 | 0.0359 (7) | 0.0483 (8) | 0.0511 (9) | −0.0052 (7) | 0.0108 (6) | 0.0035 (7) |
C15 | 0.0418 (8) | 0.0453 (9) | 0.0541 (9) | 0.0085 (7) | 0.0145 (7) | −0.0002 (7) |
C16 | 0.0466 (8) | 0.0345 (7) | 0.0426 (7) | −0.0004 (7) | 0.0092 (6) | −0.0019 (6) |
C17 | 0.0417 (8) | 0.0610 (10) | 0.0299 (7) | −0.0068 (7) | 0.0029 (6) | 0.0093 (7) |
C18 | 0.0328 (6) | 0.0351 (7) | 0.0343 (7) | 0.0007 (6) | 0.0041 (5) | 0.0005 (6) |
C19 | 0.0310 (6) | 0.0357 (7) | 0.0377 (7) | −0.0011 (5) | 0.0012 (5) | −0.0002 (6) |
C20 | 0.0332 (9) | 0.0321 (9) | 0.0350 (9) | 0.000 | 0.0033 (7) | 0.000 |
O1—C8 | 1.4013 (16) | C8—H8B | 0.9900 |
O1—C7 | 1.4247 (18) | C9—H9A | 0.9900 |
O2—C9 | 1.4141 (16) | C9—H9B | 0.9900 |
O2—C8 | 1.4198 (16) | C10—O3i | 1.4165 (15) |
O3—C9 | 1.4136 (16) | C10—H10 | 0.9900 |
O3—C10 | 1.4167 (15) | C10—H10i | 0.9900 |
O4—C18 | 1.4018 (16) | C11—C12 | 1.383 (2) |
O4—C17 | 1.4380 (16) | C11—C16 | 1.391 (2) |
O5—C18 | 1.4130 (16) | C11—C17 | 1.498 (2) |
O5—C19 | 1.4149 (17) | C12—C13 | 1.391 (2) |
O6—C20 | 1.4135 (15) | C12—H12 | 0.9500 |
O6—C19 | 1.4184 (17) | C13—C14 | 1.374 (2) |
C1—C2 | 1.387 (2) | C13—H13 | 0.9500 |
C1—C6 | 1.389 (2) | C14—C15 | 1.375 (2) |
C1—C7 | 1.509 (2) | C14—H14 | 0.9500 |
C2—C3 | 1.3865 (19) | C15—C16 | 1.389 (2) |
C2—H2 | 0.9500 | C15—H15 | 0.9500 |
C3—C4 | 1.367 (2) | C16—H16 | 0.9500 |
C3—H3 | 0.9500 | C17—H17A | 0.9900 |
C4—C5 | 1.371 (3) | C17—H17B | 0.9900 |
C4—H4 | 0.9500 | C18—H18A | 0.9900 |
C5—C6 | 1.386 (3) | C18—H18B | 0.9900 |
C5—H5 | 0.9500 | C19—H19A | 0.9900 |
C6—H6 | 0.9500 | C19—H19B | 0.9900 |
C7—H7A | 0.9900 | C20—O6ii | 1.4135 (15) |
C7—H7B | 0.9900 | C20—H20 | 0.9900 |
C8—H8A | 0.9900 | C20—H20ii | 0.9900 |
C8—O1—C7 | 114.31 (10) | O3i—C10—H10i | 109.1 |
C9—O2—C8 | 114.11 (9) | O3—C10—H10i | 109.1 |
C9—O3—C10 | 114.45 (8) | H10—C10—H10i | 107.9 |
C18—O4—C17 | 113.74 (10) | C12—C11—C16 | 118.94 (13) |
C18—O5—C19 | 114.16 (10) | C12—C11—C17 | 120.43 (14) |
C20—O6—C19 | 114.45 (8) | C16—C11—C17 | 120.61 (14) |
C2—C1—C6 | 118.02 (14) | C11—C12—C13 | 120.46 (14) |
C2—C1—C7 | 121.31 (12) | C11—C12—H12 | 119.8 |
C6—C1—C7 | 120.58 (14) | C13—C12—H12 | 119.8 |
C3—C2—C1 | 121.25 (13) | C14—C13—C12 | 119.96 (15) |
C3—C2—H2 | 119.4 | C14—C13—H13 | 120.0 |
C1—C2—H2 | 119.4 | C12—C13—H13 | 120.0 |
C4—C3—C2 | 120.07 (17) | C13—C14—C15 | 120.30 (14) |
C4—C3—H3 | 120.0 | C13—C14—H14 | 119.8 |
C2—C3—H3 | 120.0 | C15—C14—H14 | 119.8 |
C3—C4—C5 | 119.47 (17) | C14—C15—C16 | 119.93 (14) |
C3—C4—H4 | 120.3 | C14—C15—H15 | 120.0 |
C5—C4—H4 | 120.3 | C16—C15—H15 | 120.0 |
C4—C5—C6 | 121.05 (15) | C15—C16—C11 | 120.38 (14) |
C4—C5—H5 | 119.5 | C15—C16—H16 | 119.8 |
C6—C5—H5 | 119.5 | C11—C16—H16 | 119.8 |
C5—C6—C1 | 120.14 (16) | O4—C17—C11 | 108.10 (11) |
C5—C6—H6 | 119.9 | O4—C17—H17A | 110.1 |
C1—C6—H6 | 119.9 | C11—C17—H17A | 110.1 |
O1—C7—C1 | 114.37 (12) | O4—C17—H17B | 110.1 |
O1—C7—H7A | 108.7 | C11—C17—H17B | 110.1 |
C1—C7—H7A | 108.7 | H17A—C17—H17B | 108.4 |
O1—C7—H7B | 108.7 | O4—C18—O5 | 113.14 (11) |
C1—C7—H7B | 108.7 | O4—C18—H18A | 109.0 |
H7A—C7—H7B | 107.6 | O5—C18—H18A | 109.0 |
O1—C8—O2 | 112.58 (12) | O4—C18—H18B | 109.0 |
O1—C8—H8A | 109.1 | O5—C18—H18B | 109.0 |
O2—C8—H8A | 109.1 | H18A—C18—H18B | 107.8 |
O1—C8—H8B | 109.1 | O5—C19—O6 | 112.23 (12) |
O2—C8—H8B | 109.1 | O5—C19—H19A | 109.2 |
H8A—C8—H8B | 107.8 | O6—C19—H19A | 109.2 |
O3—C9—O2 | 112.45 (12) | O5—C19—H19B | 109.2 |
O3—C9—H9A | 109.1 | O6—C19—H19B | 109.2 |
O2—C9—H9A | 109.1 | H19A—C19—H19B | 107.9 |
O3—C9—H9B | 109.1 | O6—C20—O6ii | 112.66 (16) |
O2—C9—H9B | 109.1 | O6—C20—H20 | 109.1 |
H9A—C9—H9B | 107.8 | O6ii—C20—H20 | 109.1 |
O3i—C10—O3 | 112.41 (16) | O6—C20—H20ii | 109.1 |
O3i—C10—H10 | 109.1 | O6ii—C20—H20ii | 109.1 |
O3—C10—H10 | 109.1 | H20—C20—H20ii | 107.8 |
C6—C1—C2—C3 | −0.5 (2) | C16—C11—C12—C13 | 1.0 (2) |
C7—C1—C2—C3 | 176.24 (13) | C17—C11—C12—C13 | −177.30 (14) |
C1—C2—C3—C4 | −0.1 (2) | C11—C12—C13—C14 | −1.2 (2) |
C2—C3—C4—C5 | 0.2 (2) | C12—C13—C14—C15 | 0.1 (2) |
C3—C4—C5—C6 | 0.4 (3) | C13—C14—C15—C16 | 1.2 (2) |
C4—C5—C6—C1 | −1.0 (2) | C14—C15—C16—C11 | −1.4 (2) |
C2—C1—C6—C5 | 1.0 (2) | C12—C11—C16—C15 | 0.3 (2) |
C7—C1—C6—C5 | −175.69 (14) | C17—C11—C16—C15 | 178.64 (13) |
C8—O1—C7—C1 | 70.25 (15) | C18—O4—C17—C11 | 165.43 (12) |
C2—C1—C7—O1 | 30.25 (18) | C12—C11—C17—O4 | 80.05 (17) |
C6—C1—C7—O1 | −153.13 (13) | C16—C11—C17—O4 | −98.27 (16) |
C7—O1—C8—O2 | 66.21 (14) | C17—O4—C18—O5 | 67.37 (14) |
C9—O2—C8—O1 | 66.01 (14) | C19—O5—C18—O4 | 68.74 (14) |
C10—O3—C9—O2 | 65.90 (13) | C18—O5—C19—O6 | 63.10 (13) |
C8—O2—C9—O3 | 66.15 (13) | C20—O6—C19—O5 | 60.80 (14) |
C9—O3—C10—O3i | 66.17 (9) | C19—O6—C20—O6ii | 66.99 (9) |
Symmetry codes: (i) −x+1, y, −z; (ii) −x+1, y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4 | 0.95 | 2.44 | 3.333 (2) | 158 |
C8—H8B···O6 | 0.99 | 2.60 | 3.511 (2) | 153 |
C10—H10···O5ii | 0.99 | 2.58 | 3.477 (2) | 150 |
C18—H18A···O2iii | 0.99 | 2.60 | 3.541 (2) | 160 |
C19—H19A···O1iv | 0.99 | 2.65 | 3.520 (2) | 147 |
C19—H19B···O3v | 0.99 | 2.64 | 3.542 (2) | 152 |
C3—H3···CgB | 0.95 | 2.92 | 3.715 | 143 |
C6—H6···CgBvi | 0.95 | 3.00 | 3.745 | 136 |
C13—H13···CgAiv | 0.95 | 3.07 | 3.704 | 126 |
C16—H16···CgAiii | 0.95 | 3.19 | 3.913 | 134 |
Symmetry codes: (ii) −x+1, y, −z+1; (iii) x, y, z+1; (iv) x, y−1, z; (v) −x+1, y−1, −z+1; (vi) x, y+1, z−1. |
Experimental details
Crystal data | |
Chemical formula | C19H24O6 |
Mr | 348.38 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 161 |
a, b, c (Å) | 40.733 (9), 5.431 (1), 8.266 (3) |
β (°) | 97.34 (2) |
V (Å3) | 1813.6 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.78 |
Crystal size (mm) | 0.55 × 0.50 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD4 diffractometer |
Absorption correction | Numerical using eight faces (SHELXTL; Sheldrick, 1996) |
Tmin, Tmax | 0.690, 0.933 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3681, 3429, 3311 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.082, 1.10 |
No. of reflections | 3429 |
No. of parameters | 228 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.12 |
Absolute structure | Flack (1983), with 1519 Friedel pairs |
Absolute structure parameter | 0.23 (15) |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4 | 0.95 | 2.44 | 3.333 (2) | 158 |
C8—H8B···O6 | 0.99 | 2.60 | 3.511 (2) | 153 |
C10—H10···O5i | 0.99 | 2.58 | 3.477 (2) | 150 |
C18—H18A···O2ii | 0.99 | 2.60 | 3.541 (2) | 160 |
C19—H19A···O1iii | 0.99 | 2.65 | 3.520 (2) | 147 |
C19—H19B···O3iv | 0.99 | 2.64 | 3.542 (2) | 152 |
C3—H3···CgB | 0.95 | 2.92 | 3.715 | 143 |
C6—H6···CgBv | 0.95 | 3.00 | 3.745 | 136 |
C13—H13···CgAiii | 0.95 | 3.07 | 3.704 | 126 |
C16—H16···CgAii | 0.95 | 3.19 | 3.913 | 134 |
Symmetry codes: (i) −x+1, y, −z+1; (ii) x, y, z+1; (iii) x, y−1, z; (iv) −x+1, y−1, −z+1; (v) x, y+1, z−1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The crystal structure of (I) was previously determined at room temperature (Noe et al., 1994). A small but significant alternation of the C—O bond lengths was reported, which was not understood at that time. To clearify this point a redetermination of (I) at low temperature has now been undertaken. Crystals of (I) undergo a reversible phase transition at approximately 140 K, accompanied by a splitting of the reflection profiles in the low temperature phase. The measurements of (I) were performed at 161 K, which is well above the phase transition temperature.
The structure of (I) is isomorphous with the crystal structure of 1,17-diphenyl-2,4,6,8,10,12,14,16-octaoxaheptadecane (Bats et al., 2007). The compound has two crystallographically independent molecules (Fig. 1), each displaying crystallographic twofold symmetry with the axis passing through the central CH2 group. The two independent molecules have different orientations of the terminal benzyl groups. The phenyl group of molecule A is synperiplanar with the C7—O1 bond. The phenyl group of molecule B is almost perpendicular to the C17—O4 bond.
In the roomtemperature determination of (I) we observed a systematic C—O bond length variation. This effect is not observed in the present low temperature structure determination. Reprocessing of the room temperature data of (I) showed this bond length variation to result from using an inappropriate weighting scheme in a polar space group.
The C—O bond lengths in the central section of each helix is almost constant. An average C—O bond length of 1.416 Å is observed in the regions C8—C8(1 - x,y,-z) and C18—C18(1 - x,y,1 - z). The polyoxymethylene helices (without the benzyl groups) behave as rigid bodies with rather large librational motion along the helix axis [46 (3)°2 for molecule A and 41 (3)°2 for molecule B], but with almost no librational motion about axes perpendicular to the molecular axis. The average C—O bond length, corrected for librational motion, is 1.421 Å. Values of 1.420 Å and 1.419 Å have been observed in the structures of the related compounds 1,15-diphenyl-heptaoxapentadecane (Bats et al., 2001) and 1,13-diphenyl-hexaoxaheptadecane (Bats et al., 2007).
The C—O—C bond angles in (I) range between 113.74 (10)° and 114.45 (8)° and are almost constant with an average value of 114.20°. The O—C—O angles range between 112.23 (12)° and 113.14 (11)° with a average values of 112.58°. The C—O—C—O torsion angles vary between 60.80 (14)° and 68.74 (14)° with an average value of 65.74°. Almost constant torsion angles, corresponding to an undisturbed helix, are found in molecule A. The helix of molecule B is slightly bend, resulting in deviations of the C—O—C—O torsion angles by up to 4° from their average value.
The crystal packing of (I) is stabilized by a number of intermolecular C—H···O and C—H···π(phenyl) interactions. It is similar to the crystal packing of the isomorphous compound reported by Bats et al. (2007).