1,1'-(Phenyl-methyl-ene)dinaphthalen-2-ol.

In the title compound, C(27)H(20)O(2), the phenyl ring is oriented with respect to the naphthalene ring systems at 57.87 (6) and 85.12 (6)°. The two naphthalene ring systems make a dihedral angle of 70.10 (4)°. In the mol-ecule, the hy-droxy groups are involved in a strong intra-molecular O-H⋯O hydrogen bond. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds occur. A weak C-H⋯π inter-action is also observed in the crystal.

Related literature

For the structures and ferroelectric properties of related compounds, see: Devi & Bhuyan (2004 ▶); Fu, Zhang, Cai, Ge et al. (2011 ▶); Fu, Zhang, Cai, Zhang, Ge, Xiong & Huang (2011 ▶); Fu, Zhang, Cai, Zhang, Ge, Xiong, Huang & Nakamura (2011 ▶); Fu et al. (2007 ▶, 2008 ▶, 2009 ▶); Fu & Xiong (2008 ▶).

Experimental

Crystal data

C27H20O2

M = 376.43

Monoclinic,

a = 12.066 (2) Å

b = 8.6178 (17) Å

c = 21.386 (6) Å

β = 122.02 (2)°

V = 1885.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.10 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury2 (2 × 2 bin mode) diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

19010 measured reflections

4317 independent reflections

2997 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.142

S = 1.06

4317 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004163/xu5462sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004163/xu5462Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004163/xu5462Isup3.cml

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

C27H20O2	F(000) = 792
Mr = 376.43	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4317 reflections
a = 12.066 (2) Å	θ = 3.1–27.5°
b = 8.6178 (17) Å	µ = 0.08 mm−1
c = 21.386 (6) Å	T = 298 K
β = 122.02 (2)°	Block, colourless
V = 1885.4 (7) Å3	0.10 × 0.03 × 0.03 mm
Z = 4

Rigaku Mercury2 (2x2 bin mode) diffractometer	4317 independent reflections
Radiation source: fine-focus sealed tube	2997 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD profile fitting scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.910, Tmax = 1.000	l = −27→27
19010 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0564P)2 + 0.4682P] where P = (Fo2 + 2Fc2)/3
4317 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.19967 (17)	0.11950 (19)	0.93766 (9)	0.0305 (4)
C2	0.30035 (19)	0.1805 (2)	0.93322 (11)	0.0368 (4)
C3	0.2816 (2)	0.2632 (2)	0.87169 (12)	0.0482 (5)
H3	0.3531	0.3020	0.8713	0.058*
C4	0.1591 (2)	0.2861 (3)	0.81308 (12)	0.0514 (6)
H4	0.1466	0.3437	0.7731	0.062*
C5	0.0501 (2)	0.2236 (2)	0.81202 (10)	0.0419 (5)
C6	−0.0781 (3)	0.2448 (3)	0.75021 (12)	0.0569 (6)
H6	−0.0903	0.3033	0.7105	0.068*
C7	−0.1830 (2)	0.1820 (3)	0.74762 (11)	0.0568 (6)
H7	−0.2667	0.1999	0.7072	0.068*
C8	−0.1651 (2)	0.0898 (3)	0.80619 (11)	0.0466 (5)
H8	−0.2370	0.0435	0.8036	0.056*
C9	−0.04327 (19)	0.0671 (2)	0.86700 (10)	0.0389 (5)
H9	−0.0340	0.0049	0.9050	0.047*
C10	0.06952 (18)	0.1356 (2)	0.87383 (9)	0.0327 (4)
C11	0.22543 (16)	0.03527 (19)	1.00723 (9)	0.0283 (4)
H11	0.1378	0.0207	0.9986	0.034*
C12	0.29752 (17)	0.1300 (2)	1.07956 (9)	0.0302 (4)
C13	0.42859 (17)	0.1136 (2)	1.13304 (10)	0.0354 (4)
C14	0.4834 (2)	0.1812 (2)	1.20371 (10)	0.0444 (5)
H14	0.5711	0.1644	1.2392	0.053*
C15	0.4102 (2)	0.2700 (2)	1.22052 (11)	0.0444 (5)
H15	0.4473	0.3108	1.2678	0.053*
C16	0.27814 (19)	0.3010 (2)	1.16688 (10)	0.0361 (4)
C17	0.2019 (2)	0.3980 (2)	1.18281 (12)	0.0465 (5)
H17	0.2396	0.4418	1.2295	0.056*
C18	0.0746 (2)	0.4288 (3)	1.13131 (12)	0.0507 (6)
H18	0.0254	0.4918	1.1429	0.061*
C19	0.0184 (2)	0.3647 (2)	1.06077 (12)	0.0437 (5)
H19	−0.0684	0.3866	1.0253	0.052*
C20	0.08900 (18)	0.2701 (2)	1.04312 (10)	0.0347 (4)
H20	0.0494	0.2297	0.9957	0.042*
C21	0.22122 (17)	0.23241 (19)	1.09552 (9)	0.0303 (4)
C22	0.27635 (16)	−0.1314 (2)	1.01420 (9)	0.0294 (4)
C23	0.28219 (18)	−0.2027 (2)	0.95793 (10)	0.0351 (4)
H23	0.2620	−0.1463	0.9161	0.042*
C24	0.3181 (2)	−0.3583 (2)	0.96341 (12)	0.0453 (5)
H24	0.3204	−0.4050	0.9249	0.054*
C25	0.3501 (2)	−0.4432 (2)	1.02521 (12)	0.0484 (5)
H25	0.3753	−0.5465	1.0290	0.058*
C26	0.3445 (2)	−0.3740 (2)	1.08149 (12)	0.0475 (5)
H26	0.3658	−0.4307	1.1234	0.057*
C27	0.3074 (2)	−0.2203 (2)	1.07578 (10)	0.0402 (5)
H27	0.3031	−0.1752	1.1140	0.048*
O1	0.42620 (13)	0.15738 (17)	0.99198 (8)	0.0499 (4)
H1	0.4672	0.1320	0.9670	0.075*
O2	0.51565 (12)	0.02732 (16)	1.12482 (7)	0.0460 (4)
H2	0.4961	0.0568	1.0819	0.069*

	U11	U22	U33	U12	U13	U23
C1	0.0414 (10)	0.0237 (8)	0.0308 (9)	0.0014 (7)	0.0222 (8)	−0.0012 (7)
C2	0.0456 (11)	0.0305 (9)	0.0414 (11)	0.0003 (8)	0.0279 (10)	−0.0019 (8)
C3	0.0693 (15)	0.0397 (12)	0.0542 (13)	−0.0073 (10)	0.0454 (13)	−0.0003 (10)
C4	0.0827 (17)	0.0401 (12)	0.0431 (12)	0.0011 (11)	0.0412 (13)	0.0074 (10)
C5	0.0634 (13)	0.0340 (10)	0.0317 (10)	0.0081 (9)	0.0274 (10)	0.0015 (8)
C6	0.0753 (17)	0.0580 (15)	0.0297 (11)	0.0189 (13)	0.0226 (12)	0.0096 (10)
C7	0.0533 (14)	0.0715 (16)	0.0290 (11)	0.0184 (12)	0.0105 (10)	−0.0018 (11)
C8	0.0426 (11)	0.0582 (13)	0.0333 (11)	0.0039 (10)	0.0162 (9)	−0.0108 (10)
C9	0.0433 (11)	0.0429 (11)	0.0280 (9)	0.0030 (9)	0.0173 (9)	−0.0009 (8)
C10	0.0443 (11)	0.0271 (9)	0.0275 (9)	0.0066 (8)	0.0196 (8)	−0.0015 (7)
C11	0.0296 (9)	0.0277 (9)	0.0277 (9)	−0.0001 (7)	0.0152 (8)	0.0000 (7)
C12	0.0355 (10)	0.0264 (9)	0.0287 (9)	−0.0024 (7)	0.0170 (8)	−0.0004 (7)
C13	0.0334 (10)	0.0337 (10)	0.0351 (10)	−0.0006 (8)	0.0155 (8)	−0.0007 (8)
C14	0.0385 (11)	0.0471 (12)	0.0332 (10)	−0.0039 (9)	0.0093 (9)	−0.0028 (9)
C15	0.0515 (13)	0.0429 (12)	0.0295 (10)	−0.0084 (9)	0.0152 (10)	−0.0102 (9)
C16	0.0487 (11)	0.0281 (9)	0.0334 (10)	−0.0058 (8)	0.0231 (9)	−0.0035 (8)
C17	0.0659 (15)	0.0395 (11)	0.0441 (12)	−0.0063 (10)	0.0360 (11)	−0.0115 (9)
C18	0.0610 (14)	0.0445 (12)	0.0611 (14)	0.0049 (10)	0.0421 (13)	−0.0086 (11)
C19	0.0437 (11)	0.0408 (11)	0.0500 (12)	0.0047 (9)	0.0271 (10)	0.0020 (10)
C20	0.0392 (10)	0.0316 (9)	0.0333 (10)	0.0015 (8)	0.0193 (9)	0.0012 (8)
C21	0.0373 (10)	0.0252 (9)	0.0307 (9)	−0.0029 (7)	0.0196 (8)	0.0006 (7)
C22	0.0288 (9)	0.0277 (9)	0.0289 (9)	−0.0015 (7)	0.0133 (7)	−0.0014 (7)
C23	0.0395 (10)	0.0323 (10)	0.0331 (9)	−0.0019 (8)	0.0189 (8)	−0.0029 (8)
C24	0.0576 (13)	0.0359 (11)	0.0475 (12)	−0.0006 (9)	0.0315 (11)	−0.0102 (9)
C25	0.0534 (13)	0.0270 (10)	0.0588 (14)	0.0034 (9)	0.0256 (11)	−0.0006 (10)
C26	0.0599 (14)	0.0343 (11)	0.0427 (12)	0.0020 (10)	0.0233 (11)	0.0090 (9)
C27	0.0543 (12)	0.0340 (10)	0.0333 (10)	−0.0010 (9)	0.0239 (10)	−0.0001 (8)
O1	0.0423 (8)	0.0567 (9)	0.0561 (9)	−0.0003 (7)	0.0299 (7)	0.0031 (8)
O2	0.0362 (7)	0.0510 (9)	0.0452 (8)	0.0079 (6)	0.0179 (7)	−0.0002 (7)

C1—C2	1.373 (3)	C14—H14	0.9300
C1—C10	1.441 (2)	C15—C16	1.410 (3)
C1—C11	1.532 (2)	C15—H15	0.9300
C2—O1	1.379 (2)	C16—C17	1.411 (3)
C2—C3	1.405 (3)	C16—C21	1.428 (2)
C3—C4	1.353 (3)	C17—C18	1.360 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.410 (3)	C18—C19	1.399 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.416 (3)	C19—C20	1.369 (3)
C5—C10	1.432 (3)	C19—H19	0.9300
C6—C7	1.351 (3)	C20—C21	1.418 (3)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.400 (3)	C22—C23	1.386 (2)
C7—H7	0.9300	C22—C27	1.392 (2)
C8—C9	1.365 (3)	C23—C24	1.395 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.418 (3)	C24—C25	1.375 (3)
C9—H9	0.9300	C24—H24	0.9300
C11—C22	1.538 (2)	C25—C26	1.377 (3)
C11—C12	1.546 (2)	C25—H25	0.9300
C11—H11	0.9800	C26—C27	1.383 (3)
C12—C13	1.383 (3)	C26—H26	0.9300
C12—C21	1.441 (2)	C27—H27	0.9300
C13—O2	1.372 (2)	O1—H1	0.9272
C13—C14	1.415 (3)	O2—H2	0.8564
C14—C15	1.353 (3)
C2—C1—C10	117.24 (16)	C15—C14—H14	119.5
C2—C1—C11	121.17 (16)	C13—C14—H14	119.5
C10—C1—C11	121.58 (15)	C14—C15—C16	120.43 (18)
C1—C2—O1	117.96 (17)	C14—C15—H15	119.8
C1—C2—C3	123.37 (19)	C16—C15—H15	119.8
O1—C2—C3	118.66 (17)	C15—C16—C17	121.06 (18)
C4—C3—C2	119.7 (2)	C15—C16—C21	119.10 (17)
C4—C3—H3	120.1	C17—C16—C21	119.83 (19)
C2—C3—H3	120.1	C18—C17—C16	121.39 (19)
C3—C4—C5	120.69 (19)	C18—C17—H17	119.3
C3—C4—H4	119.7	C16—C17—H17	119.3
C5—C4—H4	119.7	C17—C18—C19	119.35 (19)
C4—C5—C6	120.9 (2)	C17—C18—H18	120.3
C4—C5—C10	119.55 (19)	C19—C18—H18	120.3
C6—C5—C10	119.6 (2)	C20—C19—C18	121.0 (2)
C7—C6—C5	121.5 (2)	C20—C19—H19	119.5
C7—C6—H6	119.2	C18—C19—H19	119.5
C5—C6—H6	119.2	C19—C20—C21	121.51 (18)
C6—C7—C8	119.6 (2)	C19—C20—H20	119.2
C6—C7—H7	120.2	C21—C20—H20	119.2
C8—C7—H7	120.2	C20—C21—C16	116.85 (17)
C9—C8—C7	120.7 (2)	C20—C21—C12	123.08 (16)
C9—C8—H8	119.6	C16—C21—C12	120.08 (17)
C7—C8—H8	119.6	C23—C22—C27	117.70 (17)
C8—C9—C10	121.91 (19)	C23—C22—C11	122.13 (16)
C8—C9—H9	119.0	C27—C22—C11	119.94 (16)
C10—C9—H9	119.0	C22—C23—C24	120.67 (18)
C9—C10—C5	116.57 (17)	C22—C23—H23	119.7
C9—C10—C1	124.20 (16)	C24—C23—H23	119.7
C5—C10—C1	119.23 (17)	C25—C24—C23	120.60 (19)
C1—C11—C22	113.67 (14)	C25—C24—H24	119.7
C1—C11—C12	115.99 (14)	C23—C24—H24	119.7
C22—C11—C12	114.36 (14)	C24—C25—C26	119.39 (19)
C1—C11—H11	103.6	C24—C25—H25	120.3
C22—C11—H11	103.6	C26—C25—H25	120.3
C12—C11—H11	103.6	C25—C26—C27	120.10 (19)
C13—C12—C21	117.47 (16)	C25—C26—H26	120.0
C13—C12—C11	124.31 (16)	C27—C26—H26	120.0
C21—C12—C11	117.99 (15)	C26—C27—C22	121.53 (18)
O2—C13—C12	124.56 (17)	C26—C27—H27	119.2
O2—C13—C14	113.82 (16)	C22—C27—H27	119.2
C12—C13—C14	121.56 (18)	C2—O1—H1	100.1
C15—C14—C13	121.02 (18)	C13—O2—H2	100.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.93	2.49	3.335 (2)	151
O2—H2···O1	0.86	1.85	2.691 (2)	165
C19—H19···Cgii	0.93	2.71	3.478 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C22–C27 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.93	2.49	3.335 (2)	151
O2—H2⋯O1	0.86	1.85	2.691 (2)	165
C19—H19⋯Cgii	0.93	2.71	3.478 (3)	140

Symmetry codes: (i) ; (ii) .