2-[2-(Hydroxy­meth­yl)phen­yl]-1-(1-naphth­yl)ethanol

Khan, F.N.; Manivel, P.; Hathwar, V.R.; Krishnakumar, V.; Tyagi, R.

doi:10.1107/S1600536810000383

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o380

https://doi.org/10.1107/S1600536810000383

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2-[2-(Hydroxymethyl)phenyl]-1-(1-naphthyl)ethanol

F. Nawaz Khan,^a ^* P. Manivel,^a Venkatesha R. Hathwar,^b V. Krishnakumar ^a and Richa Tyagi ^c

^aChemistry Division, School of Advanced Science, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cChemistry Department, Hindu College, Delhi University, Delhi 110 007, India
^*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 17 December 2009; accepted 5 January 2010; online 16 January 2010)

The molecular conformation of the title compound, C₁₉H₁₈O₂, is stabilized by an intramolecular O—H—O hydrogen bond. In addition, intermolecular O—H—O interactions link the molecules into zigzag chains running along the c axis.

Related literature

For related structures, see: Gałdecki et al. (1984 ); Hoyos-Guerrero et al. (1983 ); Manivel et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₈O₂
M_r = 278.33
Monoclinic, C c
a = 16.207 (4) Å
b = 12.820 (3) Å
c = 7.7888 (18) Å
β = 111.172 (3)°
V = 1509.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.60 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.992
5447 measured reflections
1447 independent reflections
1216 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.085
S = 1.07
1447 reflections
198 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2ⁱ	0.87 (4)	1.94 (4)	2.721 (3)	148 (4)
O2—H2O⋯O1	0.94 (5)	1.79 (4)	2.721 (3)	169 (4)
Symmetry code: (i) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810000383/bt5147sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000383/bt5147Isup2.hkl

checkCIF report

Comment top

The molecular conformation of the title compound is stabilized by an intramolecular O—H—O hydrogen bond. In addition, intermolecular O—H—O interactions link the molecules to zigzag chains running along the c axis.

Related literature top

For related structures, see: Gałdecki et al. (1984); Hoyos-Guerrero et al. (1983); Manivel et al. (2009).

Experimental top

3-(naphthalen-1-yl)isocoumarin (1 eq.) was dissolved in 10 volumes of methanol, sodium borohydride (4 eq.) was added to it and stirred at 50° C under nitrogen atmosphere for 4 hrs. Then two more equivalents of NaBH₄ was further added and left overnight at 50° C for completion of the reaction. After TLC analysis, solvent methanol was removed, extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried with anhydrous Na₂SO₄, evaporated to yield the title compound, which was further purified by washing with petroleum ether. Single-crystals for the structure analysis were obtained by slow evaporation of the ethanol solution.

Structure description top

For related structures, see: Gałdecki et al. (1984); Hoyos-Guerrero et al. (1983); Manivel et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP diagram of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing diagram. The dotted lines indicate intermolecular O—H···O hydrogen bonds.

2-[2-(Hydroxymethyl)phenyl]-1-(1-naphthyl)ethanol top

Crystal data top

C₁₉H₁₈O₂	F(000) = 592
M_r = 278.33	D_x = 1.225 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2097 reflections
a = 16.207 (4) Å	θ = 2.7–26.3°
b = 12.820 (3) Å	µ = 0.08 mm⁻¹
c = 7.7888 (18) Å	T = 290 K
β = 111.172 (3)°	Needle, colorless
V = 1509.2 (6) Å³	0.60 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1447 independent reflections
Radiation source: fine-focus sealed tube	1216 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 25.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.943, T_max = 0.992	k = −15→15
5447 measured reflections	l = −9→9

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0524P)²] where P = (F_o² + 2F_c²)/3
1447 reflections	(Δ/σ)_max < 0.001
198 parameters	Δρ_max = 0.15 e Å⁻³
2 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₉H₁₈O₂	V = 1509.2 (6) Å³
M_r = 278.33	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 16.207 (4) Å	µ = 0.08 mm⁻¹
b = 12.820 (3) Å	T = 290 K
c = 7.7888 (18) Å	0.60 × 0.10 × 0.10 mm
β = 111.172 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1447 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1216 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.992	R_int = 0.039
5447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.15 e Å⁻³
1447 reflections	Δρ_min = −0.14 e Å⁻³
198 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.07843 (13)	0.13119 (13)	0.4503 (3)	0.0541 (5)
H1O	0.074 (2)	0.091 (3)	0.357 (6)	0.100 (13)*
O2	0.05537 (13)	0.04804 (13)	0.7513 (3)	0.0541 (5)
H2O	0.068 (3)	0.070 (3)	0.647 (6)	0.112 (14)*
C1	0.12467 (16)	0.27456 (16)	0.2976 (3)	0.0391 (5)
C2	0.03809 (18)	0.2984 (2)	0.2052 (4)	0.0513 (6)
H2	−0.0052	0.2669	0.2399	0.062*
C3	0.0124 (2)	0.3708 (2)	0.0562 (4)	0.0633 (8)
H3	−0.0472	0.3859	−0.0056	0.076*
C4	0.0748 (2)	0.4177 (2)	0.0047 (4)	0.0609 (8)
H4	0.0575	0.4648	−0.0926	0.073*
C5	0.2323 (3)	0.4454 (2)	0.0452 (4)	0.0681 (9)
H5	0.2157	0.4922	−0.0527	0.082*
C6	0.3193 (3)	0.4256 (2)	0.1359 (5)	0.0760 (9)
H6	0.3617	0.4597	0.1020	0.091*
C7	0.3451 (2)	0.3536 (2)	0.2810 (5)	0.0672 (8)
H7	0.4049	0.3393	0.3419	0.081*
C8	0.28404 (18)	0.30420 (19)	0.3341 (4)	0.0514 (7)
H8	0.3029	0.2566	0.4305	0.062*
C9	0.19190 (16)	0.32361 (16)	0.2457 (3)	0.0405 (5)
C10	0.16515 (18)	0.39629 (17)	0.0958 (3)	0.0476 (6)
C11	0.15080 (17)	0.19895 (15)	0.4609 (3)	0.0414 (5)
H11	0.2007	0.1563	0.4591	0.050*
C12	0.17832 (17)	0.25725 (16)	0.6467 (3)	0.0445 (6)
H12A	0.2115	0.3191	0.6400	0.053*
H12B	0.1254	0.2799	0.6668	0.053*
C13	0.23412 (17)	0.19156 (17)	0.8103 (3)	0.0415 (5)
C14	0.32550 (19)	0.1898 (2)	0.8541 (4)	0.0556 (7)
H14	0.3500	0.2320	0.7877	0.067*
C15	0.3809 (2)	0.1274 (2)	0.9933 (4)	0.0640 (8)
H15	0.4415	0.1270	1.0184	0.077*
C16	0.3454 (2)	0.0655 (2)	1.0947 (4)	0.0625 (8)
H16	0.3818	0.0223	1.1868	0.075*
C17	0.2558 (2)	0.06847 (18)	1.0582 (3)	0.0551 (7)
H17	0.2325	0.0283	1.1292	0.066*
C18	0.19887 (17)	0.13022 (15)	0.9173 (3)	0.0430 (6)
C19	0.1015 (2)	0.1264 (2)	0.8835 (4)	0.0537 (7)
H19A	0.0936	0.1123	0.9990	0.064*
H19B	0.0756	0.1940	0.8399	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0811 (13)	0.0413 (9)	0.0459 (10)	−0.0112 (9)	0.0300 (9)	−0.0034 (8)
O2	0.0705 (11)	0.0446 (9)	0.0504 (10)	−0.0041 (8)	0.0259 (9)	0.0052 (8)
C1	0.0571 (15)	0.0258 (10)	0.0338 (12)	0.0073 (10)	0.0156 (11)	−0.0023 (10)
C2	0.0587 (17)	0.0462 (14)	0.0491 (15)	0.0068 (12)	0.0194 (13)	−0.0007 (12)
C3	0.0707 (18)	0.0563 (16)	0.0486 (16)	0.0238 (15)	0.0042 (14)	0.0046 (14)
C4	0.093 (2)	0.0376 (13)	0.0428 (15)	0.0156 (15)	0.0134 (15)	0.0089 (12)
C5	0.119 (3)	0.0344 (14)	0.0600 (18)	−0.0026 (16)	0.0431 (19)	0.0079 (13)
C6	0.098 (3)	0.0610 (19)	0.084 (2)	−0.0149 (18)	0.051 (2)	0.0039 (18)
C7	0.0674 (19)	0.0587 (18)	0.081 (2)	−0.0007 (14)	0.0338 (17)	0.0029 (16)
C8	0.0678 (18)	0.0395 (13)	0.0498 (16)	0.0080 (12)	0.0248 (14)	0.0057 (12)
C9	0.0617 (16)	0.0258 (10)	0.0339 (12)	0.0059 (10)	0.0172 (11)	−0.0024 (9)
C10	0.0792 (19)	0.0254 (10)	0.0388 (14)	0.0043 (11)	0.0220 (14)	−0.0010 (10)
C11	0.0572 (14)	0.0286 (10)	0.0410 (13)	0.0049 (11)	0.0210 (11)	0.0027 (10)
C12	0.0638 (17)	0.0292 (11)	0.0421 (13)	−0.0002 (11)	0.0211 (12)	0.0019 (10)
C13	0.0595 (17)	0.0294 (11)	0.0350 (12)	−0.0003 (10)	0.0162 (11)	−0.0034 (9)
C14	0.0640 (19)	0.0554 (16)	0.0471 (15)	−0.0051 (14)	0.0197 (13)	−0.0004 (13)
C15	0.0588 (17)	0.0668 (18)	0.0540 (18)	0.0036 (14)	0.0055 (14)	−0.0052 (15)
C16	0.083 (2)	0.0468 (15)	0.0401 (15)	0.0099 (14)	0.0012 (14)	0.0023 (12)
C17	0.091 (2)	0.0349 (13)	0.0390 (14)	−0.0010 (13)	0.0228 (14)	−0.0008 (11)
C18	0.0658 (17)	0.0276 (10)	0.0372 (13)	0.0008 (10)	0.0205 (12)	−0.0053 (10)
C19	0.078 (2)	0.0406 (14)	0.0529 (16)	0.0035 (12)	0.0364 (14)	0.0016 (12)

Geometric parameters (Å, º) top

O1—C11	1.438 (3)	C8—H8	0.9300
O1—H1O	0.87 (4)	C9—C10	1.433 (3)
O2—C19	1.439 (3)	C11—C12	1.544 (3)
O2—H2O	0.94 (5)	C11—H11	0.9800
C1—C2	1.361 (3)	C12—C13	1.523 (3)
C1—C9	1.437 (3)	C12—H12A	0.9700
C1—C11	1.533 (3)	C12—H12B	0.9700
C2—C3	1.425 (4)	C13—C14	1.395 (4)
C2—H2	0.9300	C13—C18	1.408 (3)
C3—C4	1.356 (5)	C14—C15	1.386 (4)
C3—H3	0.9300	C14—H14	0.9300
C4—C10	1.404 (4)	C15—C16	1.382 (4)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.353 (5)	C16—C17	1.375 (5)
C5—C10	1.430 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.397 (3)
C6—C7	1.402 (5)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.504 (4)
C7—C8	1.358 (4)	C19—H19A	0.9700
C7—H7	0.9300	C19—H19B	0.9700
C8—C9	1.422 (4)

C11—O1—H1O	103 (3)	C1—C11—C12	111.80 (16)
C19—O2—H2O	101 (3)	O1—C11—H11	108.8
C2—C1—C9	119.7 (2)	C1—C11—H11	108.8
C2—C1—C11	120.3 (2)	C12—C11—H11	108.8
C9—C1—C11	120.0 (2)	C13—C12—C11	113.55 (17)
C1—C2—C3	121.3 (3)	C13—C12—H12A	108.9
C1—C2—H2	119.4	C11—C12—H12A	108.9
C3—C2—H2	119.4	C13—C12—H12B	108.9
C4—C3—C2	120.0 (3)	C11—C12—H12B	108.9
C4—C3—H3	120.0	H12A—C12—H12B	107.7
C2—C3—H3	120.0	C14—C13—C18	117.9 (2)
C3—C4—C10	121.1 (2)	C14—C13—C12	118.1 (2)
C3—C4—H4	119.4	C18—C13—C12	124.0 (2)
C10—C4—H4	119.4	C15—C14—C13	122.1 (3)
C6—C5—C10	121.8 (3)	C15—C14—H14	119.0
C6—C5—H5	119.1	C13—C14—H14	119.0
C10—C5—H5	119.1	C16—C15—C14	119.5 (3)
C5—C6—C7	119.7 (3)	C16—C15—H15	120.2
C5—C6—H6	120.2	C14—C15—H15	120.2
C7—C6—H6	120.2	C17—C16—C15	119.5 (3)
C8—C7—C6	120.9 (3)	C17—C16—H16	120.3
C8—C7—H7	119.5	C15—C16—H16	120.3
C6—C7—H7	119.5	C16—C17—C18	121.8 (2)
C7—C8—C9	121.6 (2)	C16—C17—H17	119.1
C7—C8—H8	119.2	C18—C17—H17	119.1
C9—C8—H8	119.2	C17—C18—C13	119.2 (2)
C8—C9—C10	117.6 (2)	C17—C18—C19	118.2 (2)
C8—C9—C1	123.9 (2)	C13—C18—C19	122.6 (2)
C10—C9—C1	118.5 (2)	O2—C19—C18	112.9 (2)
C4—C10—C5	122.2 (2)	O2—C19—H19A	109.0
C4—C10—C9	119.5 (2)	C18—C19—H19A	109.0
C5—C10—C9	118.3 (3)	O2—C19—H19B	109.0
O1—C11—C1	111.1 (2)	C18—C19—H19B	109.0
O1—C11—C12	107.45 (19)	H19A—C19—H19B	107.8

C9—C1—C2—C3	0.5 (3)	C2—C1—C11—O1	23.3 (3)
C11—C1—C2—C3	178.2 (2)	C9—C1—C11—O1	−159.00 (19)
C1—C2—C3—C4	−0.3 (4)	C2—C1—C11—C12	−96.7 (3)
C2—C3—C4—C10	0.0 (4)	C9—C1—C11—C12	81.0 (2)
C10—C5—C6—C7	1.4 (5)	O1—C11—C12—C13	78.1 (2)
C5—C6—C7—C8	−1.0 (5)	C1—C11—C12—C13	−159.79 (19)
C6—C7—C8—C9	−0.2 (4)	C11—C12—C13—C14	86.8 (3)
C7—C8—C9—C10	0.9 (3)	C11—C12—C13—C18	−91.5 (3)
C7—C8—C9—C1	−179.2 (3)	C18—C13—C14—C15	2.4 (3)
C2—C1—C9—C8	179.7 (2)	C12—C13—C14—C15	−176.0 (2)
C11—C1—C9—C8	2.1 (3)	C13—C14—C15—C16	−0.9 (4)
C2—C1—C9—C10	−0.4 (3)	C14—C15—C16—C17	−1.2 (4)
C11—C1—C9—C10	−178.10 (18)	C15—C16—C17—C18	1.9 (4)
C3—C4—C10—C5	−179.4 (3)	C16—C17—C18—C13	−0.3 (3)
C3—C4—C10—C9	0.1 (4)	C16—C17—C18—C19	178.3 (2)
C6—C5—C10—C4	178.8 (3)	C14—C13—C18—C17	−1.8 (3)
C6—C5—C10—C9	−0.7 (4)	C12—C13—C18—C17	176.5 (2)
C8—C9—C10—C4	180.0 (2)	C14—C13—C18—C19	179.7 (2)
C1—C9—C10—C4	0.2 (3)	C12—C13—C18—C19	−2.0 (3)
C8—C9—C10—C5	−0.5 (3)	C17—C18—C19—O2	−90.6 (3)
C1—C9—C10—C5	179.7 (2)	C13—C18—C19—O2	88.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.87 (4)	1.94 (4)	2.721 (3)	148 (4)
O2—H2O···O1	0.94 (5)	1.79 (4)	2.721 (3)	169 (4)

Symmetry code: (i) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O₂
M_r	278.33
Crystal system, space group	Monoclinic, Cc
Temperature (K)	290
a, b, c (Å)	16.207 (4), 12.820 (3), 7.7888 (18)
β (°)	111.172 (3)
V (Å³)	1509.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5447, 1447, 1216
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.085, 1.07
No. of reflections	1447
No. of parameters	198
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2ⁱ	0.87 (4)	1.94 (4)	2.721 (3)	148 (4)
O2—H2O···O1	0.94 (5)	1.79 (4)	2.721 (3)	169 (4)

Symmetry code: (i) x, −y, z−1/2.

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

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