organic compounds
The molecules of the title compound, C16H12O4, are linked by hydrogen bonds involving the two hydroxy and carbonyl O atoms, forming a three-dimensional network.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008408/bt6628sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008408/bt6628Isup2.hkl |
CCDC reference: 270245
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(5,6-Dihydroxy-2-methyl-1-benzofuran-3-yl) phenyl ketone top
Crystal data top
C16H12O4 | F(000) = 1120 |
Mr = 268.26 | Dx = 1.435 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 909 reflections |
a = 6.7936 (9) Å | θ = 1.9–27.1° |
b = 16.988 (2) Å | µ = 0.10 mm−1 |
c = 21.515 (3) Å | T = 295 K |
V = 2483.0 (6) Å3 | Block, colourless |
Z = 8 | 0.52 × 0.31 × 0.25 mm |
Data collection top
Bruker SMART area-detector diffractometer | 2165 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 27.1°, θmin = 1.9° |
φ and ω scans | h = −8→8 |
13857 measured reflections | k = −21→20 |
2725 independent reflections | l = −24→27 |
Refinement top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0626P)2 + 0.7622P] where P = (Fo2 + 2Fc2)/3 |
2725 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.22 e Å−3 |
2 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.0129 (2) | 0.4664 (1) | 0.6593 (1) | 0.0468 (3) | |
O2 | 0.2995 (2) | 0.4271 (1) | 0.7328 (1) | 0.0494 (3) | |
O3 | 0.6807 (2) | 0.3537 (1) | 0.5505 (1) | 0.0438 (3) | |
O4 | 0.2235 (2) | 0.4623 (1) | 0.4252 (1) | 0.0476 (3) | |
C1 | 0.1975 (2) | 0.4334 (1) | 0.5670 (1) | 0.0361 (3) | |
C2 | 0.1795 (2) | 0.4393 (1) | 0.6306 (1) | 0.0352 (3) | |
C3 | 0.3345 (2) | 0.4172 (1) | 0.6705 (1) | 0.0365 (3) | |
C4 | 0.5068 (2) | 0.3867 (1) | 0.6470 (1) | 0.0391 (3) | |
C5 | 0.5201 (2) | 0.3812 (1) | 0.5831 (1) | 0.0365 (3) | |
C6 | 0.3731 (2) | 0.4041 (1) | 0.5425 (1) | 0.0336 (3) | |
C7 | 0.4488 (2) | 0.3881 (1) | 0.4807 (1) | 0.0359 (3) | |
C8 | 0.6346 (2) | 0.3586 (1) | 0.4886 (1) | 0.0400 (3) | |
C9 | 0.7978 (2) | 0.3358 (1) | 0.4464 (1) | 0.0556 (4) | |
C10 | 0.3469 (2) | 0.4092 (1) | 0.4232 (1) | 0.0355 (3) | |
C11 | 0.3861 (2) | 0.3668 (1) | 0.3642 (1) | 0.0355 (3) | |
C12 | 0.3751 (2) | 0.4071 (1) | 0.3082 (1) | 0.0394 (3) | |
C13 | 0.4031 (2) | 0.3682 (1) | 0.2527 (1) | 0.0478 (4) | |
C14 | 0.4391 (2) | 0.2886 (1) | 0.2525 (1) | 0.0546 (4) | |
C15 | 0.4484 (3) | 0.2475 (1) | 0.3077 (1) | 0.0547 (4) | |
C16 | 0.4224 (2) | 0.2862 (1) | 0.3635 (1) | 0.0455 (4) | |
H1o | −0.063 (3) | 0.488 (1) | 0.632 (1) | 0.073 (6)* | |
H2o | 0.407 (2) | 0.431 (1) | 0.753 (1) | 0.087 (8)* | |
H1 | 0.0950 | 0.4485 | 0.5410 | 0.043* | |
H4 | 0.6090 | 0.3706 | 0.6728 | 0.047* | |
H9a | 0.9191 | 0.3576 | 0.4615 | 0.083* | |
H9b | 0.7719 | 0.3556 | 0.4055 | 0.083* | |
H9c | 0.8079 | 0.2795 | 0.4450 | 0.083* | |
H12 | 0.3486 | 0.4608 | 0.3081 | 0.047* | |
H13 | 0.3976 | 0.3958 | 0.2154 | 0.057* | |
H14 | 0.4573 | 0.2623 | 0.2150 | 0.065* | |
H15 | 0.4723 | 0.1936 | 0.3072 | 0.066* | |
H16 | 0.4292 | 0.2583 | 0.4007 | 0.055* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0438 (6) | 0.0668 (7) | 0.0299 (5) | 0.0180 (5) | 0.0026 (4) | 0.0026 (5) |
O2 | 0.0539 (7) | 0.0675 (7) | 0.0267 (5) | 0.0082 (6) | −0.0036 (5) | 0.0011 (4) |
O3 | 0.0361 (5) | 0.0550 (6) | 0.0401 (5) | 0.0115 (5) | −0.0018 (4) | 0.0026 (5) |
O4 | 0.0506 (6) | 0.0582 (7) | 0.0340 (5) | 0.0205 (5) | 0.0005 (4) | 0.0025 (4) |
C1 | 0.0343 (7) | 0.0434 (7) | 0.0307 (7) | 0.0059 (6) | −0.0037 (5) | 0.0031 (5) |
C2 | 0.0361 (7) | 0.0389 (7) | 0.0307 (7) | 0.0030 (6) | 0.0009 (5) | 0.0019 (5) |
C3 | 0.0439 (8) | 0.0384 (7) | 0.0272 (6) | 0.0007 (6) | −0.0035 (5) | 0.0030 (5) |
C4 | 0.0393 (7) | 0.0435 (8) | 0.0346 (7) | 0.0039 (6) | −0.0087 (6) | 0.0050 (6) |
C5 | 0.0335 (7) | 0.0391 (7) | 0.0368 (7) | 0.0043 (6) | −0.0010 (5) | 0.0026 (6) |
C6 | 0.0360 (7) | 0.0359 (7) | 0.0290 (6) | 0.0028 (5) | −0.0015 (5) | 0.0031 (5) |
C7 | 0.0370 (7) | 0.0388 (7) | 0.0319 (7) | 0.0049 (6) | 0.0021 (5) | 0.0015 (5) |
C8 | 0.0393 (8) | 0.0443 (8) | 0.0366 (7) | 0.0048 (6) | 0.0007 (6) | 0.0019 (6) |
C9 | 0.0409 (9) | 0.0753 (12) | 0.0508 (9) | 0.0125 (8) | 0.0061 (7) | −0.0031 (8) |
C10 | 0.0342 (7) | 0.0392 (7) | 0.0332 (7) | 0.0023 (6) | 0.0030 (5) | 0.0039 (5) |
C11 | 0.0319 (7) | 0.0399 (7) | 0.0346 (7) | −0.0005 (6) | 0.0013 (5) | 0.0003 (5) |
C12 | 0.0387 (7) | 0.0429 (7) | 0.0365 (7) | 0.0019 (6) | 0.0016 (6) | 0.0011 (6) |
C13 | 0.0449 (8) | 0.0635 (10) | 0.0351 (7) | −0.0003 (7) | 0.0031 (6) | −0.0029 (7) |
C14 | 0.0457 (9) | 0.0672 (10) | 0.0508 (9) | 0.0000 (8) | 0.0014 (7) | −0.0237 (8) |
C15 | 0.0514 (9) | 0.0422 (8) | 0.0706 (11) | 0.0000 (7) | −0.0018 (8) | −0.0155 (8) |
C16 | 0.0469 (9) | 0.0394 (8) | 0.0504 (9) | −0.0022 (7) | −0.0013 (7) | 0.0024 (6) |
Geometric parameters (Å, º) top
O1—C2 | 1.369 (2) | C11—C16 | 1.392 (2) |
O2—C3 | 1.372 (2) | C12—C13 | 1.378 (2) |
O3—C8 | 1.370 (2) | C13—C14 | 1.375 (2) |
O3—C5 | 1.379 (2) | C14—C15 | 1.377 (3) |
O4—C10 | 1.233 (2) | C15—C16 | 1.381 (2) |
C1—C2 | 1.379 (2) | O1—H1o | 0.86 (1) |
C1—C6 | 1.396 (2) | O2—H2o | 0.85 (1) |
C2—C3 | 1.409 (2) | C1—H1 | 0.93 |
C3—C4 | 1.376 (2) | C4—H4 | 0.93 |
C4—C5 | 1.381 (2) | C9—H9a | 0.96 |
C5—C6 | 1.382 (2) | C9—H9b | 0.96 |
C6—C7 | 1.451 (2) | C9—H9c | 0.96 |
C7—C8 | 1.368 (2) | C12—H12 | 0.93 |
C7—C10 | 1.463 (2) | C13—H13 | 0.93 |
C8—C9 | 1.484 (2) | C14—H14 | 0.93 |
C10—C11 | 1.483 (2) | C15—H15 | 0.93 |
C11—C12 | 1.389 (2) | C16—H16 | 0.93 |
C8—O3—C5 | 107.0 (1) | C13—C12—C11 | 120.6 (1) |
C2—C1—C6 | 118.5 (1) | C14—C13—C12 | 119.9 (2) |
O1—C2—C1 | 123.1 (1) | C13—C14—C15 | 120.3 (2) |
O1—C2—C3 | 115.7 (1) | C14—C15—C16 | 120.2 (2) |
C1—C2—C3 | 121.2 (1) | C15—C16—C11 | 120.0 (2) |
O2—C3—C4 | 123.5 (1) | C2—O1—H1o | 110 (1) |
O2—C3—C2 | 115.6 (1) | C3—O2—H2o | 111 (2) |
C4—C3—C2 | 120.9 (1) | C2—C1—H1 | 120.8 |
C3—C4—C5 | 116.5 (1) | C6—C1—H1 | 120.8 |
O3—C5—C4 | 125.5 (1) | C3—C4—H4 | 121.8 |
O3—C5—C6 | 110.2 (1) | C5—C4—H4 | 121.8 |
C4—C5—C6 | 124.3 (1) | C8—C9—H9a | 109.5 |
C5—C6—C1 | 118.6 (1) | C8—C9—H9b | 109.5 |
C5—C6—C7 | 105.7 (1) | H9a—C9—H9b | 109.5 |
C1—C6—C7 | 135.7 (1) | C8—C9—H9c | 109.5 |
C8—C7—C6 | 106.3 (1) | H9a—C9—H9c | 109.5 |
C8—C7—C10 | 129.2 (1) | H9b—C9—H9c | 109.5 |
C6—C7—C10 | 124.1 (1) | C13—C12—H12 | 119.7 |
C7—C8—O3 | 110.8 (1) | C11—C12—H12 | 119.7 |
C7—C8—C9 | 135.1 (1) | C14—C13—H13 | 120.1 |
O3—C8—C9 | 114.0 (1) | C12—C13—H13 | 120.1 |
O4—C10—C7 | 118.2 (1) | C13—C14—H14 | 119.8 |
O4—C10—C11 | 120.5 (1) | C15—C14—H14 | 119.8 |
C7—C10—C11 | 121.3 (1) | C14—C15—H15 | 119.9 |
C12—C11—C16 | 119.1 (1) | C16—C15—H15 | 119.9 |
C12—C11—C10 | 119.6 (1) | C15—C16—H16 | 120.0 |
C16—C11—C10 | 121.3 (1) | C11—C16—H16 | 120.0 |
C6—C1—C2—O1 | −179.3 (1) | C6—C7—C8—O3 | 1.0 (2) |
C6—C1—C2—C3 | 0.5 (2) | C10—C7—C8—O3 | 174.3 (1) |
O1—C2—C3—O2 | −1.2 (2) | C6—C7—C8—C9 | −174.8 (2) |
C1—C2—C3—O2 | 179.0 (1) | C10—C7—C8—C9 | −1.4 (3) |
O1—C2—C3—C4 | 177.9 (1) | C5—O3—C8—C7 | −0.3 (2) |
C1—C2—C3—C4 | −1.9 (2) | C5—O3—C8—C9 | 176.4 (1) |
O2—C3—C4—C5 | −179.3 (1) | C8—C7—C10—O4 | −150.1 (2) |
C2—C3—C4—C5 | 1.6 (2) | C6—C7—C10—O4 | 22.2 (2) |
C8—O3—C5—C4 | −179.5 (1) | C8—C7—C10—C11 | 31.5 (2) |
C8—O3—C5—C6 | −0.5 (2) | C6—C7—C10—C11 | −156.2 (1) |
C3—C4—C5—O3 | 178.8 (1) | O4—C10—C11—C12 | 34.4 (2) |
C3—C4—C5—C6 | −0.1 (2) | C7—C10—C11—C12 | −147.2 (1) |
O3—C5—C6—C1 | 179.7 (1) | O4—C10—C11—C16 | −141.7 (2) |
C4—C5—C6—C1 | −1.3 (2) | C7—C10—C11—C16 | 36.7 (2) |
O3—C5—C6—C7 | 1.03 (16) | C16—C11—C12—C13 | −1.1 (2) |
C4—C5—C6—C7 | −179.9 (1) | C10—C11—C12—C13 | −177.3 (1) |
C2—C1—C6—C5 | 1.0 (2) | C11—C12—C13—C14 | 1.0 (2) |
C2—C1—C6—C7 | 179.2 (2) | C12—C13—C14—C15 | −0.3 (2) |
C5—C6—C7—C8 | −1.2 (2) | C13—C14—C15—C16 | −0.3 (3) |
C1—C6—C7—C8 | −179.5 (2) | C14—C15—C16—C11 | 0.2 (2) |
C5—C6—C7—C10 | −175.0 (1) | C12—C11—C16—C15 | 0.5 (2) |
C1—C6—C7—C10 | 6.7 (3) | C10—C11—C16—C15 | 176.7 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O4i | 0.86 (1) | 1.86 (1) | 2.711 (1) | 177 (2) |
O2—H2o···O1ii | 0.85 (1) | 2.11 (2) | 2.817 (2) | 141 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1/2, y, −z+3/2. |