Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010378/sj6065sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010378/sj6065Isup2.hkl |
CCDC reference: 272111
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C21H14O4 | F(000) = 688 |
Mr = 330.32 | Dx = 1.419 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4328 reflections |
a = 10.5756 (6) Å | θ = 2.9–25.1° |
b = 10.5907 (6) Å | µ = 0.10 mm−1 |
c = 14.4795 (8) Å | T = 293 K |
β = 107.548 (1)° | Block, colourless |
V = 1546.28 (15) Å3 | 0.47 × 0.45 × 0.23 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2918 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.022 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 2.4° |
Tmin = 0.963, Tmax = 0.987 | h = −13→13 |
10025 measured reflections | k = −13→10 |
3717 independent reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0789P)2 + 0.1717P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.31 e Å−3 |
3717 reflections | Δρmin = −0.22 e Å−3 |
226 parameters |
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 | ||
O1 | 0.77165 (13) | 0.81851 (10) | 0.18396 (8) | 0.0638 (3) | |
O2 | 0.98001 (10) | 0.54251 (11) | 0.21628 (8) | 0.0550 (3) | |
O3 | 0.62251 (11) | 0.36982 (10) | 0.29165 (8) | 0.0521 (3) | |
O4 | 0.65758 (9) | 0.60111 (8) | 0.09972 (6) | 0.0396 (2) | |
C1 | 0.64455 (14) | 0.49214 (14) | 0.32260 (10) | 0.0452 (3) | |
C2 | 0.60597 (16) | 0.52300 (18) | 0.40357 (11) | 0.0591 (4) | |
H2A | 0.5621 | 0.464 | 0.4304 | 0.071* | |
C3 | 0.63294 (19) | 0.6407 (2) | 0.44343 (12) | 0.0671 (5) | |
H3A | 0.6071 | 0.662 | 0.4974 | 0.081* | |
C4 | 0.69841 (18) | 0.72797 (18) | 0.40370 (12) | 0.0636 (5) | |
H4A | 0.7175 | 0.8074 | 0.4319 | 0.076* | |
C5 | 0.73619 (15) | 0.69906 (15) | 0.32222 (10) | 0.0500 (4) | |
C6 | 0.81599 (18) | 0.78986 (15) | 0.28536 (12) | 0.0579 (4) | |
H6A | 0.8572 | 0.8592 | 0.3289 | 0.069* | |
C7 | 0.88910 (16) | 0.74344 (14) | 0.21995 (11) | 0.0531 (4) | |
H7A | 0.974 | 0.7841 | 0.2245 | 0.064* | |
C8 | 0.88024 (13) | 0.60379 (13) | 0.20363 (9) | 0.0409 (3) | |
C9 | 0.74192 (12) | 0.54395 (12) | 0.18732 (8) | 0.0345 (3) | |
C10 | 0.70572 (13) | 0.57914 (13) | 0.27833 (9) | 0.0399 (3) | |
C11 | 0.74153 (11) | 0.40225 (12) | 0.17420 (9) | 0.0348 (3) | |
C12 | 0.79392 (12) | 0.34325 (12) | 0.10356 (9) | 0.0369 (3) | |
C13 | 0.83876 (14) | 0.41179 (14) | 0.03513 (10) | 0.0444 (3) | |
H13A | 0.8317 | 0.4994 | 0.0332 | 0.053* | |
C14 | 0.89218 (16) | 0.35140 (18) | −0.02810 (12) | 0.0581 (4) | |
H14A | 0.9194 | 0.3984 | −0.0729 | 0.07* | |
C15 | 0.90629 (18) | 0.21989 (19) | −0.02609 (13) | 0.0656 (5) | |
H15A | 0.9467 | 0.1801 | −0.0671 | 0.079* | |
C16 | 0.86032 (17) | 0.15047 (16) | 0.03646 (13) | 0.0581 (4) | |
H16A | 0.869 | 0.0631 | 0.0373 | 0.07* | |
C17 | 0.79968 (13) | 0.20915 (13) | 0.09999 (10) | 0.0434 (3) | |
C18 | 0.74296 (15) | 0.13634 (14) | 0.15959 (11) | 0.0500 (4) | |
H18A | 0.7464 | 0.0487 | 0.1573 | 0.06* | |
C19 | 0.68406 (15) | 0.19230 (14) | 0.21952 (12) | 0.0503 (4) | |
H19A | 0.6434 | 0.1436 | 0.2559 | 0.06* | |
C20 | 0.68437 (13) | 0.32559 (13) | 0.22677 (10) | 0.0414 (3) | |
C21 | 0.52142 (14) | 0.60914 (17) | 0.09210 (11) | 0.0555 (4) | |
H21A | 0.4744 | 0.6485 | 0.0318 | 0.083* | |
H21B | 0.5106 | 0.6586 | 0.1448 | 0.083* | |
H21C | 0.4868 | 0.5258 | 0.0945 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0886 (9) | 0.0331 (6) | 0.0608 (7) | −0.0007 (5) | 0.0090 (6) | 0.0016 (5) |
O2 | 0.0379 (5) | 0.0572 (7) | 0.0671 (7) | −0.0044 (4) | 0.0114 (4) | −0.0093 (5) |
O3 | 0.0591 (6) | 0.0465 (6) | 0.0607 (6) | −0.0047 (5) | 0.0332 (5) | 0.0029 (5) |
O4 | 0.0409 (5) | 0.0380 (5) | 0.0371 (4) | 0.0035 (4) | 0.0073 (3) | 0.0043 (4) |
C1 | 0.0447 (7) | 0.0492 (8) | 0.0430 (7) | 0.0063 (6) | 0.0151 (6) | 0.0033 (6) |
C2 | 0.0591 (9) | 0.0749 (11) | 0.0500 (8) | 0.0127 (8) | 0.0265 (7) | 0.0067 (8) |
C3 | 0.0718 (11) | 0.0853 (13) | 0.0474 (8) | 0.0181 (10) | 0.0228 (8) | −0.0082 (8) |
C4 | 0.0729 (11) | 0.0627 (11) | 0.0501 (8) | 0.0115 (8) | 0.0107 (8) | −0.0191 (8) |
C5 | 0.0548 (8) | 0.0456 (8) | 0.0440 (7) | 0.0054 (6) | 0.0063 (6) | −0.0078 (6) |
C6 | 0.0744 (10) | 0.0368 (8) | 0.0539 (8) | −0.0047 (7) | 0.0065 (7) | −0.0104 (6) |
C7 | 0.0599 (9) | 0.0373 (8) | 0.0569 (8) | −0.0130 (7) | 0.0097 (7) | −0.0019 (6) |
C8 | 0.0427 (7) | 0.0393 (7) | 0.0386 (6) | −0.0069 (5) | 0.0092 (5) | −0.0011 (5) |
C9 | 0.0361 (6) | 0.0309 (6) | 0.0352 (6) | 0.0003 (5) | 0.0088 (4) | 0.0014 (4) |
C10 | 0.0422 (6) | 0.0396 (7) | 0.0359 (6) | 0.0042 (5) | 0.0088 (5) | −0.0007 (5) |
C11 | 0.0334 (6) | 0.0308 (6) | 0.0382 (6) | −0.0010 (4) | 0.0079 (5) | 0.0011 (5) |
C12 | 0.0327 (6) | 0.0345 (6) | 0.0403 (6) | −0.0019 (5) | 0.0064 (5) | −0.0026 (5) |
C13 | 0.0453 (7) | 0.0450 (8) | 0.0433 (7) | −0.0042 (6) | 0.0138 (5) | −0.0026 (6) |
C14 | 0.0577 (9) | 0.0704 (11) | 0.0512 (8) | −0.0083 (8) | 0.0241 (7) | −0.0099 (7) |
C15 | 0.0664 (10) | 0.0699 (12) | 0.0676 (10) | −0.0018 (9) | 0.0308 (9) | −0.0245 (9) |
C16 | 0.0573 (9) | 0.0445 (8) | 0.0690 (10) | 0.0018 (7) | 0.0138 (7) | −0.0198 (7) |
C17 | 0.0387 (6) | 0.0366 (7) | 0.0495 (7) | −0.0005 (5) | 0.0050 (5) | −0.0058 (5) |
C18 | 0.0528 (8) | 0.0285 (6) | 0.0632 (9) | −0.0039 (6) | 0.0089 (7) | −0.0005 (6) |
C19 | 0.0533 (8) | 0.0369 (7) | 0.0612 (9) | −0.0083 (6) | 0.0178 (7) | 0.0075 (6) |
C20 | 0.0409 (6) | 0.0382 (7) | 0.0454 (7) | −0.0018 (5) | 0.0137 (5) | 0.0021 (5) |
C21 | 0.0420 (7) | 0.0672 (11) | 0.0517 (8) | 0.0099 (7) | 0.0057 (6) | 0.0010 (7) |
O1—C6 | 1.433 (2) | C9—C11 | 1.5126 (17) |
O1—C7 | 1.434 (2) | C9—C10 | 1.5251 (17) |
O2—C8 | 1.2049 (17) | C11—C20 | 1.3716 (18) |
O3—C1 | 1.3676 (18) | C11—C12 | 1.4441 (18) |
O3—C20 | 1.3786 (17) | C12—C13 | 1.4201 (19) |
O4—C21 | 1.4131 (17) | C12—C17 | 1.4230 (19) |
O4—C9 | 1.4452 (14) | C13—C14 | 1.371 (2) |
C1—C10 | 1.389 (2) | C13—H13A | 0.93 |
C1—C2 | 1.391 (2) | C14—C15 | 1.400 (3) |
C2—C3 | 1.367 (3) | C14—H14A | 0.93 |
C2—H2A | 0.93 | C15—C16 | 1.365 (3) |
C3—C4 | 1.380 (3) | C15—H15A | 0.93 |
C3—H3A | 0.93 | C16—C17 | 1.414 (2) |
C4—C5 | 1.389 (2) | C16—H16A | 0.93 |
C4—H4A | 0.93 | C17—C18 | 1.418 (2) |
C5—C10 | 1.413 (2) | C18—C19 | 1.349 (2) |
C5—C6 | 1.481 (2) | C18—H18A | 0.93 |
C6—C7 | 1.476 (2) | C19—C20 | 1.415 (2) |
C6—H6A | 0.98 | C19—H19A | 0.93 |
C7—C8 | 1.496 (2) | C21—H21A | 0.96 |
C7—H7A | 0.98 | C21—H21B | 0.96 |
C8—C9 | 1.5456 (17) | C21—H21C | 0.96 |
C6—O1—C7 | 61.97 (11) | C1—C10—C5 | 117.61 (13) |
C1—O3—C20 | 118.43 (11) | C1—C10—C9 | 120.66 (12) |
C21—O4—C9 | 116.01 (10) | C5—C10—C9 | 121.70 (12) |
O3—C1—C10 | 122.30 (12) | C20—C11—C12 | 117.67 (12) |
O3—C1—C2 | 115.74 (14) | C20—C11—C9 | 120.17 (11) |
C10—C1—C2 | 121.93 (15) | C12—C11—C9 | 122.08 (11) |
C3—C2—C1 | 119.54 (17) | C13—C12—C17 | 117.25 (12) |
C3—C2—H2A | 120.2 | C13—C12—C11 | 123.58 (12) |
C1—C2—H2A | 120.2 | C17—C12—C11 | 119.16 (12) |
C2—C3—C4 | 120.12 (15) | C14—C13—C12 | 121.27 (14) |
C2—C3—H3A | 119.9 | C14—C13—H13A | 119.4 |
C4—C3—H3A | 119.9 | C12—C13—H13A | 119.4 |
C3—C4—C5 | 121.01 (16) | C13—C14—C15 | 120.88 (16) |
C3—C4—H4A | 119.5 | C13—C14—H14A | 119.6 |
C5—C4—H4A | 119.5 | C15—C14—H14A | 119.6 |
C4—C5—C10 | 119.68 (15) | C16—C15—C14 | 119.51 (15) |
C4—C5—C6 | 120.26 (14) | C16—C15—H15A | 120.2 |
C10—C5—C6 | 119.93 (13) | C14—C15—H15A | 120.2 |
O1—C6—C7 | 59.06 (11) | C15—C16—C17 | 121.14 (15) |
O1—C6—C5 | 117.44 (13) | C15—C16—H16A | 119.4 |
C7—C6—C5 | 118.73 (13) | C17—C16—H16A | 119.4 |
O1—C6—H6A | 116.4 | C16—C17—C18 | 120.99 (14) |
C7—C6—H6A | 116.4 | C16—C17—C12 | 119.67 (14) |
C5—C6—H6A | 116.4 | C18—C17—C12 | 119.34 (13) |
O1—C7—C6 | 58.97 (10) | C19—C18—C17 | 120.98 (13) |
O1—C7—C8 | 118.98 (12) | C19—C18—H18A | 119.5 |
C6—C7—C8 | 114.25 (13) | C17—C18—H18A | 119.5 |
O1—C7—H7A | 117.2 | C18—C19—C20 | 119.66 (13) |
C6—C7—H7A | 117.2 | C18—C19—H19A | 120.2 |
C8—C7—H7A | 117.2 | C20—C19—H19A | 120.2 |
O2—C8—C7 | 119.88 (12) | C11—C20—O3 | 123.79 (12) |
O2—C8—C9 | 123.19 (12) | C11—C20—C19 | 122.73 (13) |
C7—C8—C9 | 116.15 (12) | O3—C20—C19 | 113.48 (12) |
O4—C9—C11 | 109.13 (9) | O4—C21—H21A | 109.5 |
O4—C9—C10 | 113.99 (10) | O4—C21—H21B | 109.5 |
C11—C9—C10 | 111.04 (10) | H21A—C21—H21B | 109.5 |
O4—C9—C8 | 105.52 (9) | O4—C21—H21C | 109.5 |
C11—C9—C8 | 113.12 (10) | H21A—C21—H21C | 109.5 |
C10—C9—C8 | 103.91 (10) | H21B—C21—H21C | 109.5 |
C20—O3—C1—C10 | 12.27 (19) | O4—C9—C10—C1 | 106.68 (13) |
C20—O3—C1—C2 | −165.57 (13) | C11—C9—C10—C1 | −17.08 (16) |
O3—C1—C2—C3 | 175.39 (14) | C8—C9—C10—C1 | −138.99 (12) |
C10—C1—C2—C3 | −2.5 (2) | O4—C9—C10—C5 | −75.19 (15) |
C1—C2—C3—C4 | −0.2 (3) | C11—C9—C10—C5 | 161.06 (12) |
C2—C3—C4—C5 | 1.0 (3) | C8—C9—C10—C5 | 39.14 (15) |
C3—C4—C5—C10 | 0.9 (2) | O4—C9—C11—C20 | −112.43 (12) |
C3—C4—C5—C6 | −174.94 (15) | C10—C9—C11—C20 | 14.06 (16) |
C7—O1—C6—C5 | −108.67 (15) | C8—C9—C11—C20 | 130.44 (12) |
C4—C5—C6—O1 | −130.95 (16) | O4—C9—C11—C12 | 64.28 (14) |
C10—C5—C6—O1 | 53.2 (2) | C10—C9—C11—C12 | −169.23 (10) |
C4—C5—C6—C7 | 161.15 (14) | C8—C9—C11—C12 | −52.85 (15) |
C10—C5—C6—C7 | −14.7 (2) | C20—C11—C12—C13 | 170.93 (12) |
C6—O1—C7—C8 | 102.39 (15) | C9—C11—C12—C13 | −5.86 (18) |
C5—C6—C7—O1 | 106.50 (15) | C20—C11—C12—C17 | −7.94 (17) |
O1—C6—C7—C8 | −110.44 (14) | C9—C11—C12—C17 | 175.27 (11) |
C5—C6—C7—C8 | −3.9 (2) | C17—C12—C13—C14 | −3.54 (19) |
O1—C7—C8—O2 | 165.86 (13) | C11—C12—C13—C14 | 177.57 (13) |
C6—C7—C8—O2 | −127.52 (15) | C12—C13—C14—C15 | −1.1 (2) |
O1—C7—C8—C9 | −23.89 (18) | C13—C14—C15—C16 | 3.2 (3) |
C6—C7—C8—C9 | 42.73 (17) | C14—C15—C16—C17 | −0.6 (3) |
C21—O4—C9—C11 | 86.08 (13) | C15—C16—C17—C18 | 175.13 (15) |
C21—O4—C9—C10 | −38.70 (15) | C15—C16—C17—C12 | −4.1 (2) |
C21—O4—C9—C8 | −152.07 (12) | C13—C12—C17—C16 | 6.05 (19) |
O2—C8—C9—O4 | −127.70 (13) | C11—C12—C17—C16 | −175.01 (12) |
C7—C8—C9—O4 | 62.40 (13) | C13—C12—C17—C18 | −173.23 (12) |
O2—C8—C9—C11 | −8.47 (17) | C11—C12—C17—C18 | 5.72 (18) |
C7—C8—C9—C11 | −178.36 (11) | C16—C17—C18—C19 | −179.39 (14) |
O2—C8—C9—C10 | 112.06 (14) | C12—C17—C18—C19 | −0.1 (2) |
C7—C8—C9—C10 | −57.83 (14) | C17—C18—C19—C20 | −3.1 (2) |
O3—C1—C10—C5 | −173.50 (13) | C12—C11—C20—O3 | −175.40 (12) |
C2—C1—C10—C5 | 4.2 (2) | C9—C11—C20—O3 | 1.45 (19) |
O3—C1—C10—C9 | 4.7 (2) | C12—C11—C20—C19 | 4.88 (19) |
C2—C1—C10—C9 | −177.58 (13) | C9—C11—C20—C19 | −178.27 (12) |
C4—C5—C10—C1 | −3.4 (2) | C1—O3—C20—C11 | −15.67 (19) |
C6—C5—C10—C1 | 172.46 (13) | C1—O3—C20—C19 | 164.07 (12) |
C4—C5—C10—C9 | 178.44 (13) | C18—C19—C20—C11 | 0.7 (2) |
C6—C5—C10—C9 | −5.7 (2) | C18—C19—C20—O3 | −179.09 (13) |