Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004907/wn6087sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004907/wn6087Isup2.hkl |
CCDC reference: 183813
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å Some non-H atoms missing
- R factor = 0.038
- wR factor = 0.102
- Data-to-parameter ratio = 10.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
TYPE_017 Alert A _chemical_formula_weight is not data type numb. TYPE_027 Alert A _exptl_crystal_density_diffrn is not of type numb. TYPE_036 Alert A _exptl_absorpt_coefficient_mu is not of type numb. ABSMU_01 Alert A The ratio of given/expected absorption coefficient lies outside the range 0.90 <> 1.10 Calculated value of mu = 0.039 Value of mu given = 0.079 CHEMW_01 Alert A The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.90 <> 1.10 Calculated formula weight = 315.3909 Formula weight given = 630.7400
Alert Level C:
CHEMW_01 Alert C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C22 H19 O2 Atom count from _chemical_formula_moiety:C44 H38 O4 FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C22 H19 O2 Atom count from the _atom_site data: C44 H38 O4 CELLZ_01 From the CIF: _cell_formula_units_Z 1 From the CIF: _chemical_formula_sum C22 H19 O2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 22.00 44.00 -22.00 H 19.00 38.00 -19.00 O 2.00 4.00 -2.00 Difference between formula and atom_site contents detected. ALERT: Large difference may be due to a symmetry error - see SYMMG tests
5 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD-4 Software (Enraf Nonius, 1994); cell refinement: CAD-4 Software; data reduction: CAD-4 Software and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97.
C44H38O4 | Z = 1 |
Mr = 630.74 | F(000) = 334 |
Triclinic, P1 | Dx = 1.249 Mg m−3 |
Hall symbol: -P 1 | Melting point: 210-212° K |
a = 7.748 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.792 (3) Å | Cell parameters from 25 reflections |
c = 12.410 (5) Å | θ = 10–17° |
α = 92.51 (3)° | µ = 0.08 mm−1 |
β = 90.13 (3)° | T = 293 K |
γ = 96.91 (3)° | Prism, light yellow–green |
V = 838.4 (5) Å3 | 0.3 × 0.3 × 0.3 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.6° |
Graphite monochromator | h = −9→9 |
ω/2θ scans | k = −10→10 |
5886 measured reflections | l = −14→14 |
2943 independent reflections | 3 standard reflections every 7200 min |
2138 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | All H-atom parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0502P)2 + 0.1052P] where P = (Fo2 + 2Fc2)/3 |
2943 reflections | (Δ/σ)max < 0.001 |
274 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Experimental. To determine the structure of the title compound we measured reflective intensities on our CAD4 diffractometer. A stationary anode served as X-ray source. The incident X-ray beam was monochromated with a pyrrolithic graphite crystal. Reflection intensities were measured in an ω/2θ scan mode with a scan angle of (1.30 + 0.70 t g θ). Intensities were measured with an aperture of (2.70 + 0.4 t gθ) Backgrounds were obtained from analysis of the scan profile (Blessing et al., 1974) |
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 | 0.40049 (16) | −0.18029 (12) | 0.26682 (10) | 0.0590 (3) | |
C1 | 0.95731 (19) | 0.92495 (16) | 0.01648 (12) | 0.0397 (3) | |
C8 | 0.6903 (2) | 0.42967 (17) | 0.21031 (12) | 0.0428 (4) | |
C9 | 0.60446 (19) | 0.27249 (17) | 0.22458 (12) | 0.0426 (4) | |
C13 | 0.5712 (2) | 0.04317 (18) | 0.32676 (14) | 0.0492 (4) | |
H13 | 0.600 (2) | −0.011 (2) | 0.3893 (14) | 0.059* | |
C12 | 0.4622 (2) | −0.03157 (17) | 0.24853 (13) | 0.0458 (4) | |
C15 | 0.7614 (2) | 0.52010 (17) | 0.30800 (12) | 0.0432 (4) | |
C6 | 0.8630 (2) | 0.91000 (18) | 0.11132 (13) | 0.0468 (4) | |
H6 | 0.848 (2) | 0.999 (2) | 0.1569 (13) | 0.056* | |
C4 | 0.7957 (2) | 0.63693 (17) | 0.08225 (12) | 0.0434 (4) | |
C2 | 0.9643 (2) | 0.79104 (18) | −0.04618 (13) | 0.0511 (4) | |
H2 | 1.027 (2) | 0.793 (2) | −0.1137 (14) | 0.061* | |
C7 | 0.7162 (2) | 0.48489 (18) | 0.11187 (13) | 0.0473 (4) | |
H7 | 0.680 (2) | 0.4137 (19) | 0.0496 (14) | 0.057* | |
C3 | 0.8834 (2) | 0.65243 (19) | −0.01497 (13) | 0.0510 (4) | |
H3 | 0.891 (2) | 0.562 (2) | −0.0621 (14) | 0.061* | |
C14 | 0.6406 (2) | 0.19342 (18) | 0.31555 (13) | 0.0468 (4) | |
H14 | 0.719 (2) | 0.2442 (19) | 0.3710 (14) | 0.056* | |
C11 | 0.4214 (2) | 0.0448 (2) | 0.15928 (14) | 0.0525 (4) | |
H11 | 0.346 (2) | −0.005 (2) | 0.1034 (14) | 0.063* | |
C5 | 0.7863 (2) | 0.77102 (18) | 0.14410 (13) | 0.0487 (4) | |
H5 | 0.724 (2) | 0.7675 (19) | 0.2108 (14) | 0.058* | |
C10 | 0.4915 (2) | 0.1951 (2) | 0.14863 (14) | 0.0510 (4) | |
H10 | 0.459 (2) | 0.247 (2) | 0.0843 (14) | 0.061* | |
C20 | 0.6562 (2) | 0.57786 (19) | 0.38532 (13) | 0.0501 (4) | |
H20 | 0.529 (2) | 0.5513 (19) | 0.3796 (13) | 0.060* | |
O2 | 0.98523 (18) | 0.80877 (17) | 0.55581 (11) | 0.0779 (4) | |
C19 | 0.7256 (2) | 0.6744 (2) | 0.46991 (13) | 0.0530 (4) | |
H19 | 0.648 (2) | 0.716 (2) | 0.5208 (15) | 0.064* | |
C17 | 1.0100 (2) | 0.6498 (2) | 0.40436 (15) | 0.0584 (5) | |
H17 | 1.136 (3) | 0.676 (2) | 0.4126 (15) | 0.070* | |
C16 | 0.9396 (2) | 0.5551 (2) | 0.32123 (14) | 0.0520 (4) | |
H16 | 1.015 (2) | 0.5128 (19) | 0.2677 (14) | 0.062* | |
C18 | 0.9024 (2) | 0.71183 (19) | 0.47807 (13) | 0.0537 (4) | |
C21 | 0.3170 (3) | −0.2696 (3) | 0.1797 (2) | 0.0733 (6) | |
H21A | 0.197 (4) | −0.242 (3) | 0.161 (2) | 0.110* | |
H21B | 0.302 (3) | −0.376 (3) | 0.2054 (19) | 0.110* | |
H21C | 0.394 (3) | −0.261 (3) | 0.112 (2) | 0.110* | |
C22 | 0.8802 (4) | 0.8879 (4) | 0.6278 (2) | 0.0968 (9) | |
H22A | 0.790 (4) | 0.948 (3) | 0.583 (2) | 0.145* | |
H22B | 0.964 (4) | 0.952 (4) | 0.672 (2) | 0.145* | |
H22C | 0.814 (4) | 0.800 (4) | 0.672 (2) | 0.145* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0668 (8) | 0.0397 (6) | 0.0674 (8) | −0.0076 (6) | 0.0030 (6) | 0.0047 (5) |
C1 | 0.0428 (8) | 0.0376 (8) | 0.0399 (8) | 0.0093 (6) | 0.0005 (6) | 0.0047 (6) |
C8 | 0.0447 (9) | 0.0368 (8) | 0.0467 (9) | 0.0044 (7) | 0.0043 (7) | 0.0018 (7) |
C9 | 0.0433 (8) | 0.0393 (8) | 0.0450 (9) | 0.0036 (7) | 0.0032 (7) | 0.0031 (7) |
C13 | 0.0578 (10) | 0.0421 (9) | 0.0478 (9) | 0.0040 (8) | −0.0005 (8) | 0.0071 (7) |
C12 | 0.0455 (9) | 0.0376 (8) | 0.0531 (9) | 0.0001 (7) | 0.0063 (7) | 0.0024 (7) |
C15 | 0.0497 (9) | 0.0347 (8) | 0.0447 (9) | 0.0013 (7) | 0.0031 (7) | 0.0052 (7) |
C6 | 0.0572 (10) | 0.0354 (8) | 0.0479 (9) | 0.0070 (7) | 0.0113 (7) | −0.0002 (7) |
C4 | 0.0494 (9) | 0.0374 (8) | 0.0434 (9) | 0.0046 (7) | −0.0004 (7) | 0.0051 (7) |
C2 | 0.0724 (12) | 0.0404 (9) | 0.0406 (9) | 0.0068 (8) | 0.0133 (8) | 0.0035 (7) |
C7 | 0.0565 (10) | 0.0380 (9) | 0.0464 (9) | 0.0021 (7) | 0.0018 (7) | 0.0000 (7) |
C3 | 0.0720 (11) | 0.0382 (9) | 0.0418 (9) | 0.0042 (8) | 0.0063 (8) | −0.0015 (7) |
C14 | 0.0522 (10) | 0.0419 (9) | 0.0450 (9) | 0.0012 (7) | −0.0030 (7) | 0.0009 (7) |
C11 | 0.0504 (10) | 0.0509 (10) | 0.0529 (10) | −0.0069 (8) | −0.0061 (8) | 0.0004 (8) |
C5 | 0.0588 (10) | 0.0401 (9) | 0.0474 (9) | 0.0057 (7) | 0.0154 (8) | 0.0037 (7) |
C10 | 0.0528 (10) | 0.0506 (10) | 0.0485 (10) | −0.0009 (8) | −0.0060 (8) | 0.0089 (8) |
C20 | 0.0475 (10) | 0.0497 (10) | 0.0519 (10) | 0.0010 (8) | 0.0058 (8) | 0.0016 (8) |
O2 | 0.0716 (9) | 0.0890 (10) | 0.0707 (9) | 0.0123 (8) | −0.0162 (7) | −0.0294 (8) |
C19 | 0.0576 (11) | 0.0541 (10) | 0.0476 (10) | 0.0092 (8) | 0.0080 (8) | −0.0016 (8) |
C17 | 0.0465 (10) | 0.0636 (11) | 0.0642 (11) | 0.0059 (9) | −0.0036 (9) | −0.0054 (9) |
C16 | 0.0485 (10) | 0.0539 (10) | 0.0533 (10) | 0.0062 (8) | 0.0051 (8) | −0.0035 (8) |
C18 | 0.0599 (11) | 0.0516 (10) | 0.0488 (10) | 0.0063 (8) | −0.0072 (8) | −0.0039 (8) |
C21 | 0.0753 (14) | 0.0532 (12) | 0.0839 (15) | −0.0198 (11) | −0.0041 (12) | −0.0040 (11) |
C22 | 0.1007 (19) | 0.109 (2) | 0.0778 (17) | 0.0183 (16) | −0.0105 (14) | −0.0472 (15) |
O1—C12 | 1.3660 (19) | C7—H7 | 0.990 (17) |
O1—C21 | 1.415 (2) | C3—H3 | 0.970 (18) |
C1—C2 | 1.389 (2) | C14—H14 | 0.973 (17) |
C1—C6 | 1.390 (2) | C11—C10 | 1.379 (2) |
C1—C1i | 1.478 (3) | C11—H11 | 0.964 (18) |
C8—C7 | 1.341 (2) | C5—H5 | 0.959 (17) |
C8—C9 | 1.478 (2) | C10—H10 | 0.983 (18) |
C8—C15 | 1.487 (2) | C20—C19 | 1.386 (2) |
C9—C10 | 1.383 (2) | C20—H20 | 0.986 (18) |
C9—C14 | 1.397 (2) | O2—C18 | 1.365 (2) |
C13—C12 | 1.376 (2) | O2—C22 | 1.425 (3) |
C13—C14 | 1.378 (2) | C19—C18 | 1.372 (3) |
C13—H13 | 0.969 (18) | C19—H19 | 0.962 (18) |
C12—C11 | 1.376 (2) | C17—C16 | 1.367 (2) |
C15—C20 | 1.380 (2) | C17—C18 | 1.377 (3) |
C15—C16 | 1.386 (2) | C17—H17 | 0.98 (2) |
C6—C5 | 1.372 (2) | C16—H16 | 0.977 (17) |
C6—H6 | 0.965 (17) | C21—H21A | 1.01 (3) |
C4—C5 | 1.388 (2) | C21—H21B | 1.00 (3) |
C4—C3 | 1.390 (2) | C21—H21C | 1.03 (2) |
C4—C7 | 1.465 (2) | C22—H22A | 1.09 (3) |
C2—C3 | 1.374 (2) | C22—H22B | 0.96 (3) |
C2—H2 | 0.971 (18) | C22—H22C | 1.05 (3) |
C12—O1—C21 | 117.36 (15) | C12—C11—C10 | 119.63 (16) |
C2—C1—C6 | 116.06 (14) | C12—C11—H11 | 121.2 (11) |
C2—C1—C1i | 122.06 (17) | C10—C11—H11 | 119.1 (11) |
C6—C1—C1i | 121.87 (17) | C6—C5—C4 | 121.33 (15) |
C7—C8—C9 | 121.25 (14) | C6—C5—H5 | 118.9 (10) |
C7—C8—C15 | 120.70 (14) | C4—C5—H5 | 119.8 (10) |
C9—C8—C15 | 117.83 (13) | C11—C10—C9 | 122.14 (16) |
C10—C9—C14 | 117.04 (15) | C11—C10—H10 | 117.7 (10) |
C10—C9—C8 | 122.64 (14) | C9—C10—H10 | 120.1 (10) |
C14—C9—C8 | 120.27 (14) | C15—C20—C19 | 121.25 (16) |
C12—C13—C14 | 120.32 (16) | C15—C20—H20 | 119.3 (10) |
C12—C13—H13 | 119.3 (10) | C19—C20—H20 | 119.4 (10) |
C14—C13—H13 | 120.4 (10) | C18—O2—C22 | 117.58 (17) |
O1—C12—C11 | 124.35 (15) | C18—C19—C20 | 119.56 (16) |
O1—C12—C13 | 115.94 (15) | C18—C19—H19 | 121.2 (11) |
C11—C12—C13 | 119.70 (15) | C20—C19—H19 | 119.2 (11) |
C20—C15—C16 | 117.58 (15) | C16—C17—C18 | 119.74 (17) |
C20—C15—C8 | 122.52 (15) | C16—C17—H17 | 121.5 (11) |
C16—C15—C8 | 119.84 (14) | C18—C17—H17 | 118.7 (11) |
C5—C6—C1 | 122.51 (15) | C17—C16—C15 | 121.76 (16) |
C5—C6—H6 | 117.0 (10) | C17—C16—H16 | 120.1 (10) |
C1—C6—H6 | 120.5 (10) | C15—C16—H16 | 118.1 (10) |
C5—C4—C3 | 116.28 (15) | O2—C18—C19 | 124.84 (16) |
C5—C4—C7 | 124.29 (15) | O2—C18—C17 | 115.17 (16) |
C3—C4—C7 | 119.41 (14) | C19—C18—C17 | 119.99 (16) |
C3—C2—C1 | 121.48 (15) | O1—C21—H21A | 114.3 (14) |
C3—C2—H2 | 118.1 (10) | O1—C21—H21B | 104.4 (14) |
C1—C2—H2 | 120.4 (10) | H21A—C21—H21B | 107 (2) |
C8—C7—C4 | 128.93 (15) | O1—C21—H21C | 109.8 (14) |
C8—C7—H7 | 116.7 (10) | H21A—C21—H21C | 109 (2) |
C4—C7—H7 | 114.3 (10) | H21B—C21—H21C | 111.5 (19) |
C2—C3—C4 | 122.24 (15) | O2—C22—H22A | 110.7 (16) |
C2—C3—H3 | 118.3 (10) | O2—C22—H22B | 103.4 (18) |
C4—C3—H3 | 119.5 (10) | H22A—C22—H22B | 116 (2) |
C13—C14—C9 | 121.13 (16) | O2—C22—H22C | 103.5 (17) |
C13—C14—H14 | 119.3 (10) | H22A—C22—H22C | 112 (2) |
C9—C14—H14 | 119.5 (10) | H22B—C22—H22C | 111 (2) |
C21—O1—C12—C11 | 12.6 (2) | C7—C8—C9—C10 | −24.7 (2) |
C21—O1—C12—C13 | −167.84 (16) | C7—C8—C9—C14 | 152.94 (16) |
C22—O2—C18—C17 | 173.99 (19) | C15—C8—C9—C10 | 160.69 (15) |
C22—O2—C18—C19 | −6.1 (3) | C9—C8—C15—C16 | 111.56 (17) |
C6—C1—C1i—C2i | 1.0 (2) | C9—C8—C15—C20 | −71.5 (2) |
C6—C1—C1i—C6i | −180.00 (15) | C8—C9—C10—C11 | 175.47 (15) |
C6—C1—C2—C3 | −0.5 (2) | C10—C9—C14—C13 | 2.2 (2) |
C1i—C1—C2—C3 | −179.56 (15) | C14—C9—C10—C11 | −2.2 (2) |
C2—C1—C6—C5 | 2.4 (2) | C8—C9—C14—C13 | −175.49 (15) |
C1i—C1—C6—C5 | −178.54 (15) | C9—C10—C11—C12 | 0.8 (2) |
C2—C1—C1i—C2i | 180.00 (15) | C10—C11—C12—C13 | 0.6 (2) |
C2—C1—C1i—C6i | −1.0 (2) | C10—C11—C12—O1 | −179.81 (15) |
C1—C2—C3—C4 | −2.4 (2) | O1—C12—C13—C14 | 179.82 (15) |
C2—C3—C4—C7 | −178.38 (15) | C11—C12—C13—C14 | −0.6 (2) |
C2—C3—C4—C5 | 3.2 (2) | C12—C13—C14—C9 | −0.9 (2) |
C5—C4—C7—C8 | −31.7 (3) | C8—C15—C20—C19 | −173.49 (15) |
C3—C4—C5—C6 | −1.3 (2) | C20—C15—C16—C17 | −3.4 (2) |
C7—C4—C5—C6 | −179.63 (15) | C8—C15—C16—C17 | 173.74 (16) |
C3—C4—C7—C8 | 150.00 (17) | C16—C15—C20—C19 | 3.5 (2) |
C4—C5—C6—C1 | −1.5 (2) | C15—C16—C17—C18 | 0.6 (3) |
C4—C7—C8—C9 | 178.97 (15) | C16—C17—C18—O2 | −177.92 (16) |
C4—C7—C8—C15 | −6.5 (3) | C16—C17—C18—C19 | 2.2 (3) |
C15—C8—C9—C14 | −21.7 (2) | C17—C18—C19—C20 | −2.0 (3) |
C7—C8—C15—C16 | −63.1 (2) | O2—C18—C19—C20 | 178.11 (16) |
C7—C8—C15—C20 | 113.84 (19) | C18—C19—C20—C15 | −0.9 (3) |
Symmetry code: (i) −x+2, −y+2, −z. |
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