(5,6-Dihydr­oxy-2-meth­yl-1-benzofuran-3-yl) phen­yl ketone

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.

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

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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

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Computing details

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

Crystal data

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) Å^3	Block, colourless
Z = 8	0.52 × 0.31 × 0.25 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0626P)^2 + 0.7622P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O4^i	0.86 (1)	1.86 (1)	2.711 (1)	177 (2)
O2—H2o···O1^ii	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.