1-Hy-droxy-11H-benzo[b]fluoren-11-one.

The title compound, C(17)H(10)O(2), is nearly planar, the maximum atomic deviation being 0.053 (2) Å. In the mol-ecule, an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inversion-related mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds, forming dimers. π-π stacking is observed in the crystal structure, the closest centroid-centroid distance being 3.7846 (16) Å.

Related literature

For the spectroscopy and preparation of the title compound, see: Aquino et al. (2005 ▶); Tang et al. (2011 ▶). For applications of proton-transfer dyes, see: Chen & Pang (2009 ▶, 2010 ▶); Chuang et al. (2011 ▶); Han et al. (2010 ▶); Ito et al. (2011 ▶); Jung et al. (2009 ▶); Lim et al. (2011 ▶). For related structures, see: Chen et al. (2011a ▶,b ▶); Li et al. (2007 ▶); Saeed & Bolte (2007 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H10O2

M = 246.25

Monoclinic,

a = 12.474 (2) Å

b = 6.4401 (12) Å

c = 15.601 (3) Å

β = 109.188 (3)°

V = 1183.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 297 K

0.42 × 0.22 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

6331 measured reflections

2310 independent reflections

1322 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.153

S = 1.03

2310 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104760X/xu5365sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104760X/xu5365Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104760X/xu5365Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H10O2	F(000) = 512
Mr = 246.25	Dx = 1.382 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 1918 reflections
a = 12.474 (2) Å	θ = 2.7–24.7°
b = 6.4401 (12) Å	µ = 0.09 mm−1
c = 15.601 (3) Å	T = 297 K
β = 109.188 (3)°	Parallelepiped, yellow
V = 1183.6 (4) Å3	0.42 × 0.22 × 0.12 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	1322 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.087
graphite	θmax = 26.0°, θmin = 1.7°
φ and ω scans	h = −14→15
6331 measured reflections	k = −7→7
2310 independent reflections	l = −19→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.2285P] where P = (Fo2 + 2Fc2)/3
2310 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 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.

	x	y	z	Uiso*/Ueq
O1	0.66186 (16)	−0.4250 (3)	0.11797 (12)	0.0730 (6)
O2	0.88146 (17)	−0.3141 (4)	0.24218 (14)	0.0836 (6)
H2A	0.816 (3)	−0.412 (6)	0.194 (3)	0.147 (15)*
C1	0.6346 (2)	−0.2548 (4)	0.14017 (15)	0.0515 (6)
C2	0.52192 (19)	−0.1511 (3)	0.10894 (14)	0.0466 (6)
C3	0.4220 (2)	−0.2150 (4)	0.04737 (15)	0.0527 (6)
H3A	0.4171	−0.3429	0.0187	0.063*
C4	0.3259 (2)	−0.0847 (4)	0.02760 (14)	0.0505 (6)
C5	0.2190 (2)	−0.1414 (5)	−0.03430 (16)	0.0656 (7)
H5A	0.2111	−0.2688	−0.0638	0.079*
C6	0.1281 (2)	−0.0144 (6)	−0.05160 (18)	0.0764 (9)
H6A	0.0587	−0.0549	−0.0928	0.092*
C7	0.1378 (2)	0.1778 (6)	−0.00777 (19)	0.0774 (9)
H7A	0.0747	0.2637	−0.0195	0.093*
C8	0.2396 (2)	0.2395 (4)	0.05214 (17)	0.0655 (7)
H8A	0.2452	0.3682	0.0803	0.079*
C9	0.33640 (19)	0.1115 (4)	0.07200 (14)	0.0516 (6)
C10	0.4427 (2)	0.1731 (4)	0.13508 (15)	0.0538 (6)
H10A	0.4497	0.3015	0.1637	0.065*
C11	0.53325 (19)	0.0456 (3)	0.15340 (14)	0.0478 (6)
C12	0.65335 (19)	0.0694 (4)	0.21356 (13)	0.0485 (6)
C13	0.7106 (2)	0.2252 (4)	0.26996 (16)	0.0631 (7)
H13A	0.6733	0.3451	0.2778	0.076*
C14	0.8266 (2)	0.1985 (5)	0.31532 (18)	0.0714 (8)
H14A	0.8664	0.3039	0.3533	0.086*
C15	0.8842 (2)	0.0228 (5)	0.30603 (18)	0.0714 (8)
H15A	0.9617	0.0115	0.3366	0.086*
C16	0.8262 (2)	−0.1378 (4)	0.25083 (16)	0.0602 (7)
C17	0.71100 (19)	−0.1116 (4)	0.20486 (14)	0.0490 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0818 (13)	0.0622 (12)	0.0679 (12)	0.0176 (10)	0.0151 (10)	−0.0086 (9)
O2	0.0615 (12)	0.1010 (16)	0.0844 (14)	0.0228 (12)	0.0186 (10)	0.0023 (12)
C1	0.0613 (15)	0.0508 (14)	0.0419 (12)	0.0043 (12)	0.0163 (11)	0.0011 (10)
C2	0.0527 (14)	0.0471 (13)	0.0392 (11)	0.0003 (11)	0.0140 (10)	−0.0014 (10)
C3	0.0620 (15)	0.0513 (14)	0.0431 (12)	0.0013 (12)	0.0151 (11)	−0.0029 (10)
C4	0.0537 (14)	0.0595 (15)	0.0379 (11)	0.0019 (11)	0.0146 (10)	0.0028 (10)
C5	0.0568 (16)	0.0860 (19)	0.0495 (14)	−0.0037 (15)	0.0114 (12)	0.0012 (13)
C6	0.0502 (16)	0.116 (3)	0.0570 (16)	0.0029 (17)	0.0098 (13)	0.0123 (17)
C7	0.0581 (18)	0.108 (3)	0.0659 (18)	0.0236 (17)	0.0205 (14)	0.0195 (18)
C8	0.0675 (18)	0.0757 (18)	0.0571 (15)	0.0177 (14)	0.0256 (14)	0.0093 (13)
C9	0.0511 (14)	0.0645 (16)	0.0410 (12)	0.0086 (12)	0.0174 (11)	0.0086 (11)
C10	0.0636 (16)	0.0537 (14)	0.0463 (13)	0.0024 (13)	0.0211 (11)	−0.0014 (11)
C11	0.0539 (14)	0.0511 (14)	0.0402 (12)	0.0016 (11)	0.0177 (10)	0.0006 (10)
C12	0.0541 (14)	0.0552 (14)	0.0371 (11)	−0.0062 (11)	0.0161 (10)	0.0012 (10)
C13	0.0717 (19)	0.0627 (16)	0.0529 (14)	−0.0096 (14)	0.0176 (13)	−0.0059 (12)
C14	0.0688 (19)	0.080 (2)	0.0587 (16)	−0.0256 (16)	0.0121 (14)	−0.0024 (14)
C15	0.0489 (15)	0.101 (2)	0.0588 (16)	−0.0135 (16)	0.0096 (12)	0.0049 (16)
C16	0.0574 (16)	0.0745 (18)	0.0506 (14)	0.0049 (14)	0.0202 (12)	0.0085 (13)
C17	0.0492 (14)	0.0589 (15)	0.0384 (11)	−0.0019 (11)	0.0137 (10)	0.0009 (10)

O1—C1	1.231 (3)	C7—H7A	0.9300
O2—C16	1.358 (3)	C8—C9	1.409 (3)
O2—H2A	1.11 (4)	C8—H8A	0.9300
C1—C17	1.465 (3)	C9—C10	1.423 (3)
C1—C2	1.486 (3)	C10—C11	1.349 (3)
C2—C3	1.364 (3)	C10—H10A	0.9300
C2—C11	1.429 (3)	C11—C12	1.492 (3)
C3—C4	1.412 (3)	C12—C13	1.370 (3)
C3—H3A	0.9300	C12—C17	1.400 (3)
C4—C5	1.413 (3)	C13—C14	1.397 (4)
C4—C9	1.426 (3)	C13—H13A	0.9300
C5—C6	1.352 (4)	C14—C15	1.374 (4)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.399 (4)	C15—C16	1.387 (4)
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.365 (4)	C16—C17	1.390 (3)
C16—O2—H2A	105 (2)	C10—C9—C4	119.9 (2)
O1—C1—C17	125.3 (2)	C8—C9—C4	118.4 (2)
O1—C1—C2	128.8 (2)	C11—C10—C9	120.1 (2)
C17—C1—C2	105.9 (2)	C11—C10—H10A	119.9
C3—C2—C11	122.1 (2)	C9—C10—H10A	119.9
C3—C2—C1	130.0 (2)	C10—C11—C2	119.6 (2)
C11—C2—C1	107.90 (19)	C10—C11—C12	132.0 (2)
C2—C3—C4	119.3 (2)	C2—C11—C12	108.37 (19)
C2—C3—H3A	120.4	C13—C12—C17	119.8 (2)
C4—C3—H3A	120.4	C13—C12—C11	133.1 (2)
C3—C4—C5	122.5 (2)	C17—C12—C11	107.16 (19)
C3—C4—C9	119.0 (2)	C12—C13—C14	118.0 (3)
C5—C4—C9	118.5 (2)	C12—C13—H13A	121.0
C6—C5—C4	121.4 (3)	C14—C13—H13A	121.0
C6—C5—H5A	119.3	C15—C14—C13	122.6 (3)
C4—C5—H5A	119.3	C15—C14—H14A	118.7
C5—C6—C7	120.3 (3)	C13—C14—H14A	118.7
C5—C6—H6A	119.8	C14—C15—C16	119.7 (2)
C7—C6—H6A	119.8	C14—C15—H15A	120.2
C8—C7—C6	120.3 (3)	C16—C15—H15A	120.2
C8—C7—H7A	119.9	O2—C16—C17	121.5 (2)
C6—C7—H7A	119.9	O2—C16—C15	120.5 (2)
C7—C8—C9	121.1 (3)	C17—C16—C15	118.0 (3)
C7—C8—H8A	119.4	C16—C17—C12	121.9 (2)
C9—C8—H8A	119.4	C16—C17—C1	127.4 (2)
C10—C9—C8	121.7 (2)	C12—C17—C1	110.7 (2)
O1—C1—C2—C3	−1.4 (4)	C3—C2—C11—C12	−178.2 (2)
C17—C1—C2—C3	178.4 (2)	C1—C2—C11—C12	−0.1 (2)
O1—C1—C2—C11	−179.3 (2)	C10—C11—C12—C13	0.7 (4)
C17—C1—C2—C11	0.5 (2)	C2—C11—C12—C13	179.2 (2)
C11—C2—C3—C4	−1.0 (3)	C10—C11—C12—C17	−179.0 (2)
C1—C2—C3—C4	−178.6 (2)	C2—C11—C12—C17	−0.5 (2)
C2—C3—C4—C5	−179.0 (2)	C17—C12—C13—C14	1.7 (3)
C2—C3—C4—C9	0.7 (3)	C11—C12—C13—C14	−178.0 (2)
C3—C4—C5—C6	179.5 (2)	C12—C13—C14—C15	−0.6 (4)
C9—C4—C5—C6	−0.1 (3)	C13—C14—C15—C16	−1.0 (4)
C4—C5—C6—C7	−0.3 (4)	C14—C15—C16—O2	−178.8 (2)
C5—C6—C7—C8	0.7 (4)	C14—C15—C16—C17	1.5 (4)
C6—C7—C8—C9	−0.7 (4)	O2—C16—C17—C12	179.8 (2)
C7—C8—C9—C10	−179.3 (2)	C15—C16—C17—C12	−0.5 (3)
C7—C8—C9—C4	0.3 (4)	O2—C16—C17—C1	−2.8 (4)
C3—C4—C9—C10	0.0 (3)	C15—C16—C17—C1	176.9 (2)
C5—C4—C9—C10	179.7 (2)	C13—C12—C17—C16	−1.2 (3)
C3—C4—C9—C8	−179.6 (2)	C11—C12—C17—C16	178.5 (2)
C5—C4—C9—C8	0.1 (3)	C13—C12—C17—C1	−178.9 (2)
C8—C9—C10—C11	179.1 (2)	C11—C12—C17—C1	0.8 (2)
C4—C9—C10—C11	−0.4 (3)	O1—C1—C17—C16	1.4 (4)
C9—C10—C11—C2	0.2 (3)	C2—C1—C17—C16	−178.4 (2)
C9—C10—C11—C12	178.5 (2)	O1—C1—C17—C12	179.0 (2)
C3—C2—C11—C10	0.6 (3)	C2—C1—C17—C12	−0.8 (2)
C1—C2—C11—C10	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	1.11 (4)	1.90 (4)	2.877 (3)	145 (3)
C3—H3A···O1i	0.93	2.52	3.369 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	1.11 (4)	1.90 (4)	2.877 (3)	145 (3)
C3—H3A⋯O1i	0.93	2.52	3.369 (3)	151

Symmetry code: (i) .