Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026819/is6009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026819/is6009Isup2.hkl |
CCDC reference: 259091
Data collection: local software; cell refinement: local software; data reduction: local software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL97.
C16H14O4 | F(000) = 284 |
Mr = 270.27 | Dx = 1.349 Mg m−3 |
Monoclinic, P21 | Melting point: 370 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71069 Å |
a = 6.215 (7) Å | Cell parameters from 35 reflections |
b = 7.491 (7) Å | θ = 4.4–10.6° |
c = 14.461 (15) Å | µ = 0.10 mm−1 |
β = 98.68 (8)° | T = 95 K |
V = 665.5 (12) Å3 | Needle, colorless |
Z = 2 | 0.42 × 0.25 × 0.12 mm |
Stoe diffractometer | Rint = 0.087 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.9° |
Graphite monochromator | h = −7→7 |
ω scans | k = −3→8 |
1612 measured reflections | l = −1→17 |
1270 independent reflections | 3 standard reflections every 100 reflections |
943 reflections with I > 2σ(I) | intensity decay: 0.1% |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.1091P] where P = (Fo2 + 2Fc2)/3 |
1270 reflections | (Δ/σ)max < 0.001 |
175 parameters | Δρmax = 0.28 e Å−3 |
1 restraint | Δρmin = −0.28 e Å−3 |
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. The non-hydrogen atoms were refined with anisotropic displacement parameters. The C atoms of the phenyl rings were fitted to a regular hexagon with C—C distances of 1.39 Å (AFIX 66 of SHELXL97). The H atoms of the phenyl rings were put at the external bisector of the C—C—C angle at a C—H distance of 0.95 Å and common isotropic displacement parameters were refined for the H atoms of the same phenyl group (AFIX 43 of SHELXL97). The H-atoms H3 and H92 were put at the external bisector of the C—C—C angle at a C—H distance of 0.95 Å (AFIX 43 of SHELXL97). The H-atoms bonded to C8 were refined with an idealized geometry with approximately tetrahedral angles and C—H distances of 0.99 Å (AFIX 23 of SHELXL97). The H-atoms bonded to C3 and C8 were refined with a common isotropic displacement parameter. The individual isotropic displacement parameter of H92 was free to refine. The H-atoms bonded to C93 were refined with common isotropic displacement parameters and idealized geometry with the H-atoms in the C9—C92—C93 plane, angles of 120°, and C—H distances of 0.95 Å (AFIX 93 of SHELXL97). The H-atoms of the methyl group were refined with one common isotropic displacement parameter and idealized geometry with tetrahedral angles, enabling rotation around the X—C bond, and C—H distances of 0.98 Å (AFIX 137 of SHELXL97). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.3240 (6) | 0.3111 (7) | 0.7857 (3) | 0.0168 (11) | |
C2 | 0.1557 (10) | 0.3580 (9) | 0.8335 (4) | 0.0139 (15) | |
C3 | −0.0286 (9) | 0.4063 (10) | 0.7776 (4) | 0.0173 (15) | |
H3 | −0.1612 | 0.4396 | 0.7980 | 0.015 (10)* | |
C4 | 0.0084 (9) | 0.3990 (9) | 0.6818 (4) | 0.0124 (14) | |
O4 | −0.1047 (6) | 0.4382 (7) | 0.6077 (3) | 0.0191 (11) | |
C5 | 0.2496 (10) | 0.3299 (10) | 0.6881 (4) | 0.0143 (14) | |
C6 | 0.3834 (9) | 0.4642 (10) | 0.6422 (4) | 0.0156 (15) | |
O6 | 0.4724 (7) | 0.5938 (7) | 0.6773 (3) | 0.0212 (12) | |
O7 | 0.3816 (6) | 0.4185 (7) | 0.5531 (3) | 0.0199 (12) | |
C8 | 0.2756 (10) | 0.2424 (10) | 0.5343 (5) | 0.0157 (15) | |
H81 | 0.3600 | 0.1669 | 0.4965 | 0.015 (10)* | |
H82 | 0.1262 | 0.2568 | 0.5000 | 0.015 (10)* | |
C9 | 0.2700 (9) | 0.1581 (10) | 0.6303 (4) | 0.0134 (15) | |
C21 | 0.2012 (6) | 0.3355 (6) | 0.93493 (19) | 0.0152 (14) | |
C22 | 0.0536 (5) | 0.4003 (6) | 0.9900 (2) | 0.0211 (16) | |
H22 | −0.0757 | 0.4581 | 0.9616 | 0.027 (9)* | |
C23 | 0.0953 (6) | 0.3805 (7) | 1.0866 (2) | 0.0242 (18) | |
H23 | −0.0056 | 0.4248 | 1.1243 | 0.027 (9)* | |
C24 | 0.2845 (7) | 0.2960 (8) | 1.12818 (19) | 0.0222 (17) | |
H24 | 0.3130 | 0.2825 | 1.1942 | 0.027 (9)* | |
C25 | 0.4321 (5) | 0.2312 (7) | 1.0731 (3) | 0.0227 (17) | |
H25 | 0.5615 | 0.1734 | 1.1015 | 0.027 (9)* | |
C26 | 0.3904 (6) | 0.2509 (6) | 0.9765 (2) | 0.0199 (16) | |
H26 | 0.4913 | 0.2066 | 0.9388 | 0.027 (9)* | |
C91 | 0.4927 (10) | 0.0702 (11) | 0.6664 (5) | 0.0212 (17) | |
H911 | 0.4991 | 0.0388 | 0.7325 | 0.031 (12)* | |
H912 | 0.6101 | 0.1542 | 0.6594 | 0.031 (12)* | |
H913 | 0.5096 | −0.0380 | 0.6300 | 0.031 (12)* | |
C92 | 0.0759 (10) | 0.0367 (10) | 0.6315 (5) | 0.0174 (16) | |
H92 | −0.0573 | 0.0699 | 0.5943 | 0.03 (2)* | |
C93 | 0.0785 (11) | −0.1152 (10) | 0.6815 (4) | 0.0190 (16) | |
H931 | 0.2088 | −0.1526 | 0.7195 | 0.030 (14)* | |
H932 | −0.0501 | −0.1848 | 0.6788 | 0.030 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.013 (2) | 0.026 (3) | 0.013 (2) | 0.003 (2) | 0.0068 (17) | 0.003 (2) |
C2 | 0.020 (3) | 0.006 (4) | 0.019 (3) | 0.000 (3) | 0.010 (3) | −0.002 (3) |
C3 | 0.019 (3) | 0.019 (4) | 0.016 (3) | 0.002 (3) | 0.013 (3) | −0.003 (3) |
C4 | 0.017 (3) | 0.006 (3) | 0.013 (3) | −0.001 (3) | −0.003 (3) | −0.002 (3) |
O4 | 0.020 (2) | 0.023 (3) | 0.016 (2) | 0.006 (2) | 0.0053 (18) | −0.003 (2) |
C5 | 0.021 (3) | 0.016 (4) | 0.006 (3) | −0.004 (3) | 0.004 (2) | −0.003 (3) |
C6 | 0.017 (3) | 0.014 (4) | 0.014 (4) | −0.002 (3) | −0.002 (3) | −0.003 (3) |
O6 | 0.020 (2) | 0.021 (3) | 0.023 (3) | −0.001 (2) | 0.007 (2) | −0.006 (2) |
O7 | 0.020 (2) | 0.024 (3) | 0.019 (3) | −0.007 (2) | 0.0118 (18) | 0.000 (2) |
C8 | 0.017 (3) | 0.018 (4) | 0.014 (3) | −0.003 (3) | 0.008 (3) | −0.002 (3) |
C9 | 0.013 (3) | 0.018 (4) | 0.010 (3) | 0.005 (3) | 0.005 (2) | −0.003 (3) |
C21 | 0.016 (3) | 0.013 (4) | 0.018 (3) | −0.006 (3) | 0.008 (3) | −0.004 (3) |
C22 | 0.023 (3) | 0.021 (4) | 0.020 (4) | 0.002 (3) | 0.005 (3) | 0.001 (4) |
C23 | 0.032 (3) | 0.028 (5) | 0.015 (4) | 0.000 (4) | 0.010 (3) | −0.008 (3) |
C24 | 0.038 (4) | 0.021 (5) | 0.007 (3) | −0.004 (3) | 0.000 (3) | −0.002 (3) |
C25 | 0.025 (3) | 0.021 (4) | 0.022 (4) | 0.001 (3) | 0.003 (3) | 0.002 (3) |
C26 | 0.023 (3) | 0.019 (4) | 0.019 (4) | −0.004 (3) | 0.010 (3) | −0.002 (3) |
C91 | 0.019 (3) | 0.027 (5) | 0.018 (4) | 0.001 (3) | 0.005 (3) | −0.011 (3) |
C92 | 0.017 (3) | 0.018 (4) | 0.018 (4) | 0.006 (3) | 0.008 (3) | −0.002 (3) |
C93 | 0.026 (3) | 0.016 (4) | 0.017 (4) | −0.004 (3) | 0.011 (3) | −0.003 (3) |
O1—C2 | 1.383 (7) | C21—C22 | 1.3900 |
O1—C5 | 1.424 (7) | C21—C26 | 1.3900 |
C2—C3 | 1.348 (9) | C22—C23 | 1.3900 |
C2—C21 | 1.462 (7) | C22—H22 | 0.9500 |
C3—C4 | 1.439 (8) | C23—C24 | 1.3900 |
C3—H3 | 0.9500 | C23—H23 | 0.9500 |
C4—O4 | 1.225 (7) | C24—C25 | 1.3900 |
C4—C5 | 1.576 (8) | C24—H24 | 0.9500 |
C5—C6 | 1.521 (9) | C25—C26 | 1.3900 |
C5—C9 | 1.551 (9) | C25—H25 | 0.9500 |
C6—O6 | 1.193 (8) | C26—H26 | 0.9500 |
C6—O7 | 1.331 (8) | C91—H911 | 0.9800 |
O7—C8 | 1.482 (9) | C91—H912 | 0.9800 |
C8—C9 | 1.530 (9) | C91—H913 | 0.9800 |
C8—H81 | 0.9900 | C92—C93 | 1.347 (10) |
C8—H82 | 0.9900 | C92—H92 | 0.9500 |
C9—C91 | 1.550 (8) | C93—H931 | 0.9500 |
C9—C92 | 1.513 (9) | C93—H932 | 0.9500 |
C2—O1—C5 | 108.2 (5) | C91—C9—C5 | 108.2 (5) |
C3—C2—O1 | 114.0 (5) | C22—C21—C26 | 120.0 |
C3—C2—C21 | 130.6 (5) | C22—C21—C2 | 119.4 (3) |
O1—C2—C21 | 115.2 (5) | C26—C21—C2 | 120.6 (3) |
C2—C3—C4 | 108.8 (5) | C21—C22—C23 | 120.0 |
C2—C3—H3 | 125.6 | C21—C22—H22 | 120.0 |
C4—C3—H3 | 125.6 | C23—C22—H22 | 120.0 |
O4—C4—C3 | 132.7 (6) | C24—C23—C22 | 120.0 |
O4—C4—C5 | 123.0 (5) | C24—C23—H23 | 120.0 |
C3—C4—C5 | 104.2 (5) | C22—C23—H23 | 120.0 |
O1—C5—C6 | 112.4 (5) | C23—C24—C25 | 120.0 |
O1—C5—C9 | 114.3 (6) | C23—C24—H24 | 120.0 |
C6—C5—C9 | 102.6 (5) | C25—C24—H24 | 120.0 |
O1—C5—C4 | 104.7 (4) | C26—C25—C24 | 120.0 |
C6—C5—C4 | 109.6 (6) | C26—C25—H25 | 120.0 |
C9—C5—C4 | 113.3 (5) | C24—C25—H25 | 120.0 |
O6—C6—O7 | 123.9 (6) | C25—C26—C21 | 120.0 |
O6—C6—C5 | 126.9 (6) | C25—C26—H26 | 120.0 |
O7—C6—C5 | 109.1 (5) | C21—C26—H26 | 120.0 |
C6—O7—C8 | 110.2 (5) | C9—C91—H911 | 109.5 |
O7—C8—C9 | 105.7 (5) | C9—C91—H912 | 109.5 |
O7—C8—H81 | 110.6 | H911—C91—H912 | 109.5 |
C9—C8—H81 | 110.6 | C9—C91—H913 | 109.5 |
O7—C8—H82 | 110.6 | H911—C91—H913 | 109.5 |
C9—C8—H82 | 110.6 | H912—C91—H913 | 109.5 |
H81—C8—H82 | 108.7 | C93—C92—C9 | 124.7 (6) |
C92—C9—C8 | 112.7 (5) | C93—C92—H92 | 117.7 |
C92—C9—C91 | 114.4 (6) | C9—C92—H92 | 117.7 |
C8—C9—C91 | 109.8 (5) | C92—C93—H931 | 120.0 |
C92—C9—C5 | 111.3 (5) | C92—C93—H932 | 120.0 |
C8—C9—C5 | 99.3 (5) | H931—C93—H932 | 120.0 |
C5—O1—C2—C3 | 0.5 (8) | O7—C8—C9—C5 | 31.3 (5) |
C5—O1—C2—C21 | 176.4 (5) | O1—C5—C9—C92 | 84.6 (6) |
O1—C2—C3—C4 | −1.7 (8) | C6—C5—C9—C92 | −153.4 (5) |
C21—C2—C3—C4 | −176.8 (6) | C4—C5—C9—C92 | −35.3 (7) |
C2—C3—C4—O4 | −176.0 (7) | O1—C5—C9—C8 | −156.5 (5) |
C2—C3—C4—C5 | 2.0 (8) | C6—C5—C9—C8 | −34.5 (6) |
C2—O1—C5—C6 | 119.7 (6) | C4—C5—C9—C8 | 83.6 (6) |
C2—O1—C5—C9 | −123.8 (5) | O1—C5—C9—C91 | −41.9 (7) |
C2—O1—C5—C4 | 0.8 (7) | C6—C5—C9—C91 | 80.1 (6) |
O4—C4—C5—O1 | 176.6 (6) | C4—C5—C9—C91 | −161.8 (5) |
C3—C4—C5—O1 | −1.7 (7) | C3—C2—C21—C22 | −13.2 (9) |
O4—C4—C5—C6 | 55.8 (8) | O1—C2—C21—C22 | 171.8 (4) |
C3—C4—C5—C6 | −122.5 (6) | C3—C2—C21—C26 | 167.2 (6) |
O4—C4—C5—C9 | −58.2 (9) | O1—C2—C21—C26 | −7.9 (7) |
C3—C4—C5—C9 | 123.5 (6) | C26—C21—C22—C23 | 0.0 |
O1—C5—C6—O6 | −31.2 (9) | C2—C21—C22—C23 | −179.7 (5) |
C9—C5—C6—O6 | −154.5 (6) | C21—C22—C23—C24 | 0.0 |
C4—C5—C6—O6 | 84.8 (7) | C22—C23—C24—C25 | 0.0 |
O1—C5—C6—O7 | 150.8 (5) | C23—C24—C25—C26 | 0.0 |
C9—C5—C6—O7 | 27.5 (7) | C24—C25—C26—C21 | 0.0 |
C4—C5—C6—O7 | −93.1 (6) | C22—C21—C26—C25 | 0.0 |
O6—C6—O7—C8 | 174.6 (6) | C2—C21—C26—C25 | 179.7 (5) |
C5—C6—O7—C8 | −7.4 (7) | C8—C9—C92—C93 | 144.3 (6) |
C6—O7—C8—C9 | −16.2 (6) | C91—C9—C92—C93 | 17.9 (9) |
O7—C8—C9—C92 | 149.1 (5) | C5—C9—C92—C93 | −105.2 (7) |
O7—C8—C9—C91 | −82.0 (6) |