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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008408/bt6628sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008408/bt6628Isup2.hkl
Contains datablock I

CCDC reference: 270245

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.114
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT737_ALERT_1_C D...A Calc 2.711(3), Rep 2.7110(10) ...... 3.00 su-Rat O1 -O4 1.555 5.566
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

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
C16H12O4F(000) = 1120
Mr = 268.26Dx = 1.435 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 909 reflections
a = 6.7936 (9) Åθ = 1.9–27.1°
b = 16.988 (2) ŵ = 0.10 mm1
c = 21.515 (3) ÅT = 295 K
V = 2483.0 (6) Å3Block, colourless
Z = 80.52 × 0.31 × 0.25 mm
Data collection top
Bruker SMART area-detector
diffractometer
2165 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 27.1°, θmin = 1.9°
φ and ω scansh = 88
13857 measured reflectionsk = 2120
2725 independent reflectionsl = 2427
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H 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 parametersΔρmax = 0.22 e Å3
2 restraintsΔρmin = 0.18 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0129 (2)0.4664 (1)0.6593 (1)0.0468 (3)
O20.2995 (2)0.4271 (1)0.7328 (1)0.0494 (3)
O30.6807 (2)0.3537 (1)0.5505 (1)0.0438 (3)
O40.2235 (2)0.4623 (1)0.4252 (1)0.0476 (3)
C10.1975 (2)0.4334 (1)0.5670 (1)0.0361 (3)
C20.1795 (2)0.4393 (1)0.6306 (1)0.0352 (3)
C30.3345 (2)0.4172 (1)0.6705 (1)0.0365 (3)
C40.5068 (2)0.3867 (1)0.6470 (1)0.0391 (3)
C50.5201 (2)0.3812 (1)0.5831 (1)0.0365 (3)
C60.3731 (2)0.4041 (1)0.5425 (1)0.0336 (3)
C70.4488 (2)0.3881 (1)0.4807 (1)0.0359 (3)
C80.6346 (2)0.3586 (1)0.4886 (1)0.0400 (3)
C90.7978 (2)0.3358 (1)0.4464 (1)0.0556 (4)
C100.3469 (2)0.4092 (1)0.4232 (1)0.0355 (3)
C110.3861 (2)0.3668 (1)0.3642 (1)0.0355 (3)
C120.3751 (2)0.4071 (1)0.3082 (1)0.0394 (3)
C130.4031 (2)0.3682 (1)0.2527 (1)0.0478 (4)
C140.4391 (2)0.2886 (1)0.2525 (1)0.0546 (4)
C150.4484 (3)0.2475 (1)0.3077 (1)0.0547 (4)
C160.4224 (2)0.2862 (1)0.3635 (1)0.0455 (4)
H1o0.063 (3)0.488 (1)0.632 (1)0.073 (6)*
H2o0.407 (2)0.431 (1)0.753 (1)0.087 (8)*
H10.09500.44850.54100.043*
H40.60900.37060.67280.047*
H9a0.91910.35760.46150.083*
H9b0.77190.35560.40550.083*
H9c0.80790.27950.44500.083*
H120.34860.46080.30810.047*
H130.39760.39580.21540.057*
H140.45730.26230.21500.065*
H150.47230.19360.30720.066*
H160.42920.25830.40070.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0438 (6)0.0668 (7)0.0299 (5)0.0180 (5)0.0026 (4)0.0026 (5)
O20.0539 (7)0.0675 (7)0.0267 (5)0.0082 (6)0.0036 (5)0.0011 (4)
O30.0361 (5)0.0550 (6)0.0401 (5)0.0115 (5)0.0018 (4)0.0026 (5)
O40.0506 (6)0.0582 (7)0.0340 (5)0.0205 (5)0.0005 (4)0.0025 (4)
C10.0343 (7)0.0434 (7)0.0307 (7)0.0059 (6)0.0037 (5)0.0031 (5)
C20.0361 (7)0.0389 (7)0.0307 (7)0.0030 (6)0.0009 (5)0.0019 (5)
C30.0439 (8)0.0384 (7)0.0272 (6)0.0007 (6)0.0035 (5)0.0030 (5)
C40.0393 (7)0.0435 (8)0.0346 (7)0.0039 (6)0.0087 (6)0.0050 (6)
C50.0335 (7)0.0391 (7)0.0368 (7)0.0043 (6)0.0010 (5)0.0026 (6)
C60.0360 (7)0.0359 (7)0.0290 (6)0.0028 (5)0.0015 (5)0.0031 (5)
C70.0370 (7)0.0388 (7)0.0319 (7)0.0049 (6)0.0021 (5)0.0015 (5)
C80.0393 (8)0.0443 (8)0.0366 (7)0.0048 (6)0.0007 (6)0.0019 (6)
C90.0409 (9)0.0753 (12)0.0508 (9)0.0125 (8)0.0061 (7)0.0031 (8)
C100.0342 (7)0.0392 (7)0.0332 (7)0.0023 (6)0.0030 (5)0.0039 (5)
C110.0319 (7)0.0399 (7)0.0346 (7)0.0005 (6)0.0013 (5)0.0003 (5)
C120.0387 (7)0.0429 (7)0.0365 (7)0.0019 (6)0.0016 (6)0.0011 (6)
C130.0449 (8)0.0635 (10)0.0351 (7)0.0003 (7)0.0031 (6)0.0029 (7)
C140.0457 (9)0.0672 (10)0.0508 (9)0.0000 (8)0.0014 (7)0.0237 (8)
C150.0514 (9)0.0422 (8)0.0706 (11)0.0000 (7)0.0018 (8)0.0155 (8)
C160.0469 (9)0.0394 (8)0.0504 (9)0.0022 (7)0.0013 (7)0.0024 (6)
Geometric parameters (Å, º) top
O1—C21.369 (2)C11—C161.392 (2)
O2—C31.372 (2)C12—C131.378 (2)
O3—C81.370 (2)C13—C141.375 (2)
O3—C51.379 (2)C14—C151.377 (3)
O4—C101.233 (2)C15—C161.381 (2)
C1—C21.379 (2)O1—H1o0.86 (1)
C1—C61.396 (2)O2—H2o0.85 (1)
C2—C31.409 (2)C1—H10.93
C3—C41.376 (2)C4—H40.93
C4—C51.381 (2)C9—H9a0.96
C5—C61.382 (2)C9—H9b0.96
C6—C71.451 (2)C9—H9c0.96
C7—C81.368 (2)C12—H120.93
C7—C101.463 (2)C13—H130.93
C8—C91.484 (2)C14—H140.93
C10—C111.483 (2)C15—H150.93
C11—C121.389 (2)C16—H160.93
C8—O3—C5107.0 (1)C13—C12—C11120.6 (1)
C2—C1—C6118.5 (1)C14—C13—C12119.9 (2)
O1—C2—C1123.1 (1)C13—C14—C15120.3 (2)
O1—C2—C3115.7 (1)C14—C15—C16120.2 (2)
C1—C2—C3121.2 (1)C15—C16—C11120.0 (2)
O2—C3—C4123.5 (1)C2—O1—H1o110 (1)
O2—C3—C2115.6 (1)C3—O2—H2o111 (2)
C4—C3—C2120.9 (1)C2—C1—H1120.8
C3—C4—C5116.5 (1)C6—C1—H1120.8
O3—C5—C4125.5 (1)C3—C4—H4121.8
O3—C5—C6110.2 (1)C5—C4—H4121.8
C4—C5—C6124.3 (1)C8—C9—H9a109.5
C5—C6—C1118.6 (1)C8—C9—H9b109.5
C5—C6—C7105.7 (1)H9a—C9—H9b109.5
C1—C6—C7135.7 (1)C8—C9—H9c109.5
C8—C7—C6106.3 (1)H9a—C9—H9c109.5
C8—C7—C10129.2 (1)H9b—C9—H9c109.5
C6—C7—C10124.1 (1)C13—C12—H12119.7
C7—C8—O3110.8 (1)C11—C12—H12119.7
C7—C8—C9135.1 (1)C14—C13—H13120.1
O3—C8—C9114.0 (1)C12—C13—H13120.1
O4—C10—C7118.2 (1)C13—C14—H14119.8
O4—C10—C11120.5 (1)C15—C14—H14119.8
C7—C10—C11121.3 (1)C14—C15—H15119.9
C12—C11—C16119.1 (1)C16—C15—H15119.9
C12—C11—C10119.6 (1)C15—C16—H16120.0
C16—C11—C10121.3 (1)C11—C16—H16120.0
C6—C1—C2—O1179.3 (1)C6—C7—C8—O31.0 (2)
C6—C1—C2—C30.5 (2)C10—C7—C8—O3174.3 (1)
O1—C2—C3—O21.2 (2)C6—C7—C8—C9174.8 (2)
C1—C2—C3—O2179.0 (1)C10—C7—C8—C91.4 (3)
O1—C2—C3—C4177.9 (1)C5—O3—C8—C70.3 (2)
C1—C2—C3—C41.9 (2)C5—O3—C8—C9176.4 (1)
O2—C3—C4—C5179.3 (1)C8—C7—C10—O4150.1 (2)
C2—C3—C4—C51.6 (2)C6—C7—C10—O422.2 (2)
C8—O3—C5—C4179.5 (1)C8—C7—C10—C1131.5 (2)
C8—O3—C5—C60.5 (2)C6—C7—C10—C11156.2 (1)
C3—C4—C5—O3178.8 (1)O4—C10—C11—C1234.4 (2)
C3—C4—C5—C60.1 (2)C7—C10—C11—C12147.2 (1)
O3—C5—C6—C1179.7 (1)O4—C10—C11—C16141.7 (2)
C4—C5—C6—C11.3 (2)C7—C10—C11—C1636.7 (2)
O3—C5—C6—C71.03 (16)C16—C11—C12—C131.1 (2)
C4—C5—C6—C7179.9 (1)C10—C11—C12—C13177.3 (1)
C2—C1—C6—C51.0 (2)C11—C12—C13—C141.0 (2)
C2—C1—C6—C7179.2 (2)C12—C13—C14—C150.3 (2)
C5—C6—C7—C81.2 (2)C13—C14—C15—C160.3 (3)
C1—C6—C7—C8179.5 (2)C14—C15—C16—C110.2 (2)
C5—C6—C7—C10175.0 (1)C12—C11—C16—C150.5 (2)
C1—C6—C7—C106.7 (3)C10—C11—C16—C15176.7 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O4i0.86 (1)1.86 (1)2.711 (1)177 (2)
O2—H2o···O1ii0.85 (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.
 

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