11-Hy-droxy-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propano-anthracen-12-one.

In the title compound, C(20)H(18)O(2), the central six-membered ring adopts a boat conformation and the terminal benzene rings make a dihedral angle of 42.66 (4)° with each other. In the crystal structure, the O-H group forms both an intra- and an inter-molecular O-H⋯O hydrogen bond; the former generates an S(5) ring and the latter leads to inversion-generated R(2) (2)(10) loops. The dimers are further linked into ribbons propagating along the a axis by C-H⋯O inter-actions, and the packing is consolidated by weak C-H⋯π inter-actions.

Related literature

For background to benzocta­mine, see: Wilhelm & Schmidt (1969 ▶); Karama et al. (2010a ▶). For further synthetic details, see: Karama et al. (2010b ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set descriptors of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H18O2

M = 290.34

Triclinic,

a = 7.60940 (1) Å

b = 9.16090 (1) Å

c = 11.1735 (2) Å

α = 84.202 (1)°

β = 85.707 (1)°

γ = 69.895 (1)°

V = 727.02 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.57 × 0.39 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.978

14851 measured reflections

5283 independent reflections

4634 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.06

5283 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033538/hb6360sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033538/hb6360Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033538/hb6360Isup3.cml

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

C20H18O2	Z = 2
Mr = 290.34	F(000) = 308
Triclinic, P1	Dx = 1.326 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.60940 (1) Å	Cell parameters from 7628 reflections
b = 9.16090 (1) Å	θ = 2.4–32.6°
c = 11.1735 (2) Å	µ = 0.08 mm−1
α = 84.202 (1)°	T = 100 K
β = 85.707 (1)°	Block, colourless
γ = 69.895 (1)°	0.57 × 0.39 × 0.27 mm
V = 727.02 (2) Å3

Bruker SMART APEXII CCD diffractometer	5283 independent reflections
Radiation source: fine-focus sealed tube	4634 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 32.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.954, Tmax = 0.978	k = −13→13
14851 measured reflections	l = −16→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.073P)2 + 0.1953P] where P = (Fo2 + 2Fc2)/3
5283 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.68817 (9)	0.54934 (8)	−0.00032 (6)	0.01745 (14)
O2	0.37722 (10)	0.68003 (9)	0.12072 (7)	0.01983 (15)
C1	0.78621 (12)	0.92873 (9)	0.16802 (8)	0.01291 (15)
C2	0.85293 (13)	1.05379 (10)	0.15089 (8)	0.01569 (16)
H2A	0.9775	1.0374	0.1203	0.019*
C3	0.73774 (14)	1.20262 (10)	0.17841 (9)	0.01855 (17)
H3A	0.7840	1.2873	0.1686	0.022*
C4	0.55436 (14)	1.22547 (10)	0.22043 (9)	0.01800 (17)
H4A	0.4745	1.3268	0.2383	0.022*
C5	0.48627 (12)	1.10130 (10)	0.23671 (8)	0.01547 (16)
H5A	0.3600	1.1192	0.2643	0.019*
C6	0.60259 (12)	0.95029 (9)	0.21274 (8)	0.01269 (15)
C7	0.54044 (11)	0.80676 (9)	0.23205 (8)	0.01258 (15)
C8	0.70206 (12)	0.66696 (9)	0.28388 (8)	0.01320 (15)
C9	0.67772 (13)	0.55204 (10)	0.36921 (8)	0.01689 (17)
H9A	0.5554	0.5601	0.4004	0.020*
C10	0.83112 (15)	0.42584 (11)	0.40902 (9)	0.02055 (18)
H10A	0.8126	0.3484	0.4668	0.025*
C11	1.01105 (14)	0.41270 (11)	0.36456 (9)	0.02113 (19)
H11A	1.1156	0.3280	0.3934	0.025*
C12	1.03761 (13)	0.52413 (10)	0.27754 (9)	0.01737 (17)
H12A	1.1602	0.5145	0.2460	0.021*
C13	0.88421 (12)	0.64985 (9)	0.23660 (8)	0.01354 (15)
C14	0.90580 (11)	0.76761 (9)	0.13675 (8)	0.01299 (15)
H14A	1.0400	0.7611	0.1273	0.016*
C15	0.84323 (12)	0.73065 (10)	0.01665 (8)	0.01417 (15)
H15A	0.8081	0.8262	−0.0392	0.017*
H15B	0.9498	0.6507	−0.0216	0.017*
C16	0.67958 (12)	0.67252 (10)	0.03665 (8)	0.01311 (15)
C17	0.50015 (12)	0.76547 (10)	0.10507 (8)	0.01383 (15)
H17A	0.4382	0.8650	0.0557	0.017*
C18	0.35765 (12)	0.83894 (10)	0.31087 (8)	0.01568 (16)
H18A	0.2566	0.9225	0.2683	0.019*
H18B	0.3227	0.7437	0.3195	0.019*
C19	0.36715 (13)	0.88655 (11)	0.43476 (8)	0.01713 (17)
H19A	0.4780	0.8350	0.4775	0.021*
C20	0.22942 (14)	0.99649 (11)	0.48766 (9)	0.02011 (18)
H20C	0.1170	1.0500	0.4471	0.024*
H20A	0.2434	1.0216	0.5660	0.024*
H1O2	0.412 (3)	0.602 (2)	0.0653 (18)	0.048 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0180 (3)	0.0167 (3)	0.0194 (3)	−0.0076 (2)	0.0007 (2)	−0.0050 (2)
O2	0.0168 (3)	0.0261 (3)	0.0222 (3)	−0.0133 (3)	0.0034 (2)	−0.0089 (3)
C1	0.0129 (3)	0.0129 (3)	0.0139 (4)	−0.0056 (3)	−0.0012 (3)	−0.0005 (3)
C2	0.0174 (4)	0.0158 (3)	0.0161 (4)	−0.0087 (3)	−0.0010 (3)	0.0000 (3)
C3	0.0244 (4)	0.0143 (3)	0.0192 (4)	−0.0094 (3)	−0.0022 (3)	0.0000 (3)
C4	0.0224 (4)	0.0121 (3)	0.0182 (4)	−0.0039 (3)	−0.0025 (3)	−0.0014 (3)
C5	0.0153 (4)	0.0143 (3)	0.0154 (4)	−0.0031 (3)	−0.0016 (3)	−0.0013 (3)
C6	0.0127 (3)	0.0126 (3)	0.0133 (3)	−0.0049 (3)	−0.0010 (3)	−0.0010 (3)
C7	0.0112 (3)	0.0139 (3)	0.0133 (4)	−0.0050 (3)	0.0005 (3)	−0.0020 (3)
C8	0.0141 (3)	0.0131 (3)	0.0132 (4)	−0.0056 (3)	−0.0005 (3)	−0.0010 (3)
C9	0.0201 (4)	0.0159 (4)	0.0157 (4)	−0.0082 (3)	0.0014 (3)	−0.0004 (3)
C10	0.0278 (5)	0.0154 (4)	0.0179 (4)	−0.0078 (3)	−0.0010 (3)	0.0029 (3)
C11	0.0235 (4)	0.0146 (4)	0.0218 (4)	−0.0022 (3)	−0.0042 (3)	0.0017 (3)
C12	0.0151 (4)	0.0157 (4)	0.0193 (4)	−0.0025 (3)	−0.0020 (3)	−0.0010 (3)
C13	0.0134 (3)	0.0128 (3)	0.0145 (4)	−0.0046 (3)	−0.0008 (3)	−0.0009 (3)
C14	0.0115 (3)	0.0134 (3)	0.0147 (4)	−0.0053 (3)	0.0007 (3)	−0.0009 (3)
C15	0.0134 (3)	0.0154 (3)	0.0150 (4)	−0.0069 (3)	0.0025 (3)	−0.0022 (3)
C16	0.0130 (3)	0.0146 (3)	0.0119 (3)	−0.0050 (3)	0.0000 (3)	−0.0010 (3)
C17	0.0116 (3)	0.0162 (3)	0.0151 (4)	−0.0062 (3)	0.0003 (3)	−0.0027 (3)
C18	0.0129 (3)	0.0197 (4)	0.0157 (4)	−0.0071 (3)	0.0017 (3)	−0.0035 (3)
C19	0.0157 (4)	0.0214 (4)	0.0156 (4)	−0.0079 (3)	0.0014 (3)	−0.0032 (3)
C20	0.0201 (4)	0.0223 (4)	0.0188 (4)	−0.0086 (3)	0.0040 (3)	−0.0044 (3)

O1—C16	1.2198 (10)	C10—C11	1.3903 (14)
O2—C17	1.4034 (10)	C10—H10A	0.9500
O2—H1O2	0.948 (19)	C11—C12	1.3929 (13)
C1—C2	1.3957 (11)	C11—H11A	0.9500
C1—C6	1.4023 (11)	C12—C13	1.3955 (12)
C1—C14	1.5039 (11)	C12—H12A	0.9500
C2—C3	1.3945 (13)	C13—C14	1.5122 (12)
C2—H2A	0.9500	C14—C15	1.5622 (12)
C3—C4	1.3901 (14)	C14—H14A	1.0000
C3—H3A	0.9500	C15—C16	1.5081 (12)
C4—C5	1.3946 (12)	C15—H15A	0.9900
C4—H4A	0.9500	C15—H15B	0.9900
C5—C6	1.4024 (12)	C16—C17	1.5329 (12)
C5—H5A	0.9500	C17—H17A	1.0000
C6—C7	1.5342 (11)	C18—C19	1.5069 (13)
C7—C8	1.5369 (12)	C18—H18A	0.9900
C7—C18	1.5441 (12)	C18—H18B	0.9900
C7—C17	1.5822 (12)	C19—C20	1.3281 (13)
C8—C9	1.3988 (12)	C19—H19A	0.9500
C8—C13	1.4081 (12)	C20—H20C	0.9500
C9—C10	1.3939 (13)	C20—H20A	0.9500
C9—H9A	0.9500
C17—O2—H1O2	109.6 (11)	C11—C12—H12A	120.0
C2—C1—C6	120.78 (8)	C13—C12—H12A	120.0
C2—C1—C14	121.59 (8)	C12—C13—C8	120.62 (8)
C6—C1—C14	117.62 (7)	C12—C13—C14	121.59 (8)
C3—C2—C1	120.39 (8)	C8—C13—C14	117.74 (7)
C3—C2—H2A	119.8	C1—C14—C13	109.28 (7)
C1—C2—H2A	119.8	C1—C14—C15	110.01 (7)
C4—C3—C2	119.14 (8)	C13—C14—C15	109.10 (7)
C4—C3—H3A	120.4	C1—C14—H14A	109.5
C2—C3—H3A	120.4	C13—C14—H14A	109.5
C3—C4—C5	120.75 (8)	C15—C14—H14A	109.5
C3—C4—H4A	119.6	C16—C15—C14	112.12 (7)
C5—C4—H4A	119.6	C16—C15—H15A	109.2
C4—C5—C6	120.56 (8)	C14—C15—H15A	109.2
C4—C5—H5A	119.7	C16—C15—H15B	109.2
C6—C5—H5A	119.7	C14—C15—H15B	109.2
C5—C6—C1	118.33 (7)	H15A—C15—H15B	107.9
C5—C6—C7	123.79 (7)	O1—C16—C15	120.54 (8)
C1—C6—C7	117.88 (7)	O1—C16—C17	118.56 (8)
C6—C7—C8	109.17 (7)	C15—C16—C17	120.90 (7)
C6—C7—C18	111.72 (7)	O2—C17—C16	109.59 (7)
C8—C7—C18	112.73 (7)	O2—C17—C7	109.46 (7)
C6—C7—C17	108.29 (7)	C16—C17—C7	112.40 (7)
C8—C7—C17	107.27 (6)	O2—C17—H17A	108.4
C18—C7—C17	107.46 (7)	C16—C17—H17A	108.4
C9—C8—C13	118.50 (8)	C7—C17—H17A	108.4
C9—C8—C7	124.06 (8)	C19—C18—C7	115.09 (7)
C13—C8—C7	117.33 (7)	C19—C18—H18A	108.5
C10—C9—C8	120.67 (8)	C7—C18—H18A	108.5
C10—C9—H9A	119.7	C19—C18—H18B	108.5
C8—C9—H9A	119.7	C7—C18—H18B	108.5
C11—C10—C9	120.33 (8)	H18A—C18—H18B	107.5
C11—C10—H10A	119.8	C20—C19—C18	123.72 (9)
C9—C10—H10A	119.8	C20—C19—H19A	118.1
C10—C11—C12	119.80 (8)	C18—C19—H19A	118.1
C10—C11—H11A	120.1	C19—C20—H20C	120.0
C12—C11—H11A	120.1	C19—C20—H20A	120.0
C11—C12—C13	120.02 (9)	H20C—C20—H20A	120.0
C6—C1—C2—C3	0.18 (13)	C9—C8—C13—C12	−2.45 (13)
C14—C1—C2—C3	178.71 (8)	C7—C8—C13—C12	−178.77 (8)
C1—C2—C3—C4	−1.48 (14)	C9—C8—C13—C14	174.81 (8)
C2—C3—C4—C5	0.90 (14)	C7—C8—C13—C14	−1.50 (11)
C3—C4—C5—C6	1.00 (14)	C2—C1—C14—C13	136.26 (8)
C4—C5—C6—C1	−2.27 (13)	C6—C1—C14—C13	−45.17 (10)
C4—C5—C6—C7	178.01 (8)	C2—C1—C14—C15	−103.98 (9)
C2—C1—C6—C5	1.69 (13)	C6—C1—C14—C15	74.60 (9)
C14—C1—C6—C5	−176.90 (8)	C12—C13—C14—C1	−138.29 (8)
C2—C1—C6—C7	−178.58 (8)	C8—C13—C14—C1	44.47 (10)
C14—C1—C6—C7	2.83 (11)	C12—C13—C14—C15	101.38 (9)
C5—C6—C7—C8	−140.45 (8)	C8—C13—C14—C15	−75.85 (9)
C1—C6—C7—C8	39.84 (10)	C1—C14—C15—C16	−83.63 (8)
C5—C6—C7—C18	−15.07 (11)	C13—C14—C15—C16	36.24 (9)
C1—C6—C7—C18	165.21 (8)	C14—C15—C16—O1	−125.97 (9)
C5—C6—C7—C17	103.08 (9)	C14—C15—C16—C17	53.24 (10)
C1—C6—C7—C17	−76.64 (9)	O1—C16—C17—O2	4.54 (11)
C6—C7—C8—C9	143.59 (8)	C15—C16—C17—O2	−174.69 (7)
C18—C7—C8—C9	18.81 (12)	O1—C16—C17—C7	126.48 (8)
C17—C7—C8—C9	−99.29 (9)	C15—C16—C17—C7	−52.74 (10)
C6—C7—C8—C13	−40.32 (10)	C6—C7—C17—O2	−156.87 (7)
C18—C7—C8—C13	−165.10 (7)	C8—C7—C17—O2	85.43 (8)
C17—C7—C8—C13	76.81 (9)	C18—C7—C17—O2	−36.03 (9)
C13—C8—C9—C10	1.83 (13)	C6—C7—C17—C16	81.11 (8)
C7—C8—C9—C10	177.88 (8)	C8—C7—C17—C16	−36.59 (9)
C8—C9—C10—C11	0.19 (15)	C18—C7—C17—C16	−158.05 (7)
C9—C10—C11—C12	−1.64 (15)	C6—C7—C18—C19	−59.15 (10)
C10—C11—C12—C13	1.02 (15)	C8—C7—C18—C19	64.23 (10)
C11—C12—C13—C8	1.05 (14)	C17—C7—C18—C19	−177.80 (7)
C11—C12—C13—C14	−176.11 (8)	C7—C18—C19—C20	139.88 (9)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.948 (18)	2.08 (2)	2.600 (2)	113 (2)
O2—H1O2···O1i	0.948 (18)	2.01 (2)	2.8041 (10)	140 (2)
C14—H14A···O2ii	1.00	2.41	3.3909 (12)	166
C17—H17A···Cg1iii	1.00	2.92	3.6542 (10)	131
C20—H20A···Cg1iv	0.95	2.79	3.6357 (11)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.948 (18)	2.08 (2)	2.600 (2)	113 (2)
O2—H1O2⋯O1i	0.948 (18)	2.01 (2)	2.8041 (10)	140 (2)
C14—H14A⋯O2ii	1.00	2.41	3.3909 (12)	166
C17—H17A⋯Cg1iii	1.00	2.92	3.6542 (10)	131
C20—H20A⋯Cg1iv	0.95	2.79	3.6357 (11)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .