1-[(1R*,2R*)-1,2-Dihy­droxy-1,2-di­hydro­naph­thal­en-1-yl]ethan-1-one

Lough, A.J.; Hill, J.; Tam, W.

doi:10.1107/S2414314619006096

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 5| May 2019| x190609

https://doi.org/10.1107/S2414314619006096

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1-[(1R,2R)-1,2-Dihydroxy-1,2-dihydronaphthalen-1-yl]ethan-1-one

Alan J. Lough,^a ^* Jarvis Hill ^b and William Tam ^b

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada, and ^bDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
^*Correspondence e-mail: alan.lough@utoronto.ca

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 April 2019; accepted 1 May 2019; online 10 May 2019)

The crystal structure of the centrosymmetic title compound, C₁₂H₁₂O₃, confirms the relative stereochemistry. The 1,2-dihydrobenzene ring is in a flattened half-chair conformation. In the crystal, O—H⋯O hydrogen bonds link the molecules into layers lying parallel to (001).

Keywords: crystal structure; relative stereochemistry; hydrogen bonding; ring-opening reaction.

CCDC reference: 1913420

Structure description

In past years, our research group has investigated the effects of various C₁-substituted oxabenzonorbornadienes (OBDs) on controlling the regioselectivity of ring-opening reactions (Ballantine et al., 2009 ; Edmunds et al., 2015 , 2016 ; Raheem et al., 2014 ). Very recently, Yang et al. (2019 ) reported the first iridium-catalysed ring-opening reaction of oxa/aza benzonorbornadienes with various alcohol nucleophiles. Based upon these findings, we set out to determine the effect of C₁ substitution on controlling the regioselectivity of this reaction on unsymmetrical OBDs. The reaction of the C₁-substituted OBD (I) with water in the presence of [Ir(COD)Cl]₂ and tetrabutylammonium iodide afforded exclusively the C₂ regioisomer (II) in an 85% yield (Fig. 1). The relative stereochemistry of the diol system was determined by single-crystal X-ray analysis: of the cis or trans isomers potentially formed, only the trans stereoisomer was obtained.

Figure 1
The reaction scheme.

The molecular structure of the title compound is shown in Fig. 2. The 1,2-dihydrobenzene ring is in a flattened half-chair conformation. Atoms C3/C3/C5/C10 are essentially planar and atoms C1 and C2 deviate from this plane by −0.248 (1) and 0.149 (1) Å, respectively. In the crystal, O—H⋯O hydrogen bonds link the molecules (Table 1, Fig. 3) forming a two-dimensional network lying parallel to (001).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3	0.85 (2)	2.08 (2)	2.5970 (13)	118.2 (17)
O1—H1O⋯O3ⁱ	0.85 (2)	2.44 (2)	2.9568 (13)	119.8 (17)
O2—H2O⋯O1ⁱⁱ	0.87 (2)	1.92 (2)	2.7825 (12)	172.5 (16)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) -x+1, -y+1, -z+1.

Figure 2
The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

Figure 3
Part of the crystal structure of the title compound with hydrogen bonds shown as dashed lines.

Synthesis and crystallization

To a 100 ml round-bottom flask open to air was added tetrabutylammonium iodide (TBAI) (989 mg, 1 equiv), oxabenzonorbornadiene (I) (2.68 mmol), and [Ir(COD)Cl]₂ (36 mg, 2 mol%) dissolved in a 40 ml 2:1 dioxane:water mixture. This reaction was left to stir at 353 K for 45 min, after which it was cooled to room temperature and diluted in EtOAc (20 ml) and subsequently washed with EtOAc (3 × 15 ml). The combined organic layers were concentrated and the crude reaction mixture was purified by flash chromatography (EtOAc:hexanes 1:2) to obtain the ring-opened product II (462 mg, 2.26 mmol, 85%) as a white solid. The product was recrystallized from the mixed solvents of EtOAc:hexanes (2.5:7.5 v:v) to give product II as colourless crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₂O₃
M_r	204.22
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	150
a, b, c (Å)	10.8313 (4), 7.6180 (3), 24.1463 (8)
V (Å³)	1992.38 (13)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.80
Crystal size (mm)	0.21 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEX DUO CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.683, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	13267, 1782, 1742
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.088, 1.05
No. of reflections	1782
No. of parameters	145
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2018 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1913420

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619006096/hb4297sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619006096/hb4297Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: APEX3 (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

1-[(1R*,2R*)-1,2-Dihydroxy-1,2-dihydronaphthalen-1-yl]ethan-1-one top

Crystal data top

C₁₂H₁₂O₃	D_x = 1.362 Mg m⁻³
M_r = 204.22	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 9970 reflections
a = 10.8313 (4) Å	θ = 3.7–67.5°
b = 7.6180 (3) Å	µ = 0.80 mm⁻¹
c = 24.1463 (8) Å	T = 150 K
V = 1992.38 (13) Å³	Shard, colourless
Z = 8	0.21 × 0.18 × 0.16 mm
F(000) = 864

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	1742 reflections with I > 2σ(I)
Radiation source: Bruker ImuS with multi-layer optics	R_int = 0.022
φ and ω scans	θ_max = 67.5°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
T_min = 0.683, T_max = 0.753	k = −9→9
13267 measured reflections	l = −28→28
1782 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0445P)² + 0.8018P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1782 reflections	Δρ_max = 0.16 e Å⁻³
145 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Special details top

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. H atoms bonded to C atoms were placed in calculated positions and refined in a riding-model approximation with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl). H atoms bonded to O atoms were refined independently with an isotropic displacement parameter.

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

	x	y	z	U_iso*/U_eq
O1	0.42766 (8)	0.51398 (11)	0.41021 (3)	0.0251 (2)
H1O	0.352 (2)	0.490 (3)	0.4061 (8)	0.061 (6)*
O2	0.52984 (8)	0.27780 (12)	0.49706 (3)	0.0271 (2)
H2O	0.5500 (15)	0.340 (2)	0.5260 (8)	0.049 (5)*
O3	0.29996 (8)	0.22665 (14)	0.40191 (4)	0.0383 (3)
C1	0.49858 (10)	0.35827 (15)	0.40262 (4)	0.0199 (3)
C2	0.59229 (10)	0.35080 (14)	0.45046 (4)	0.0210 (3)
H2A	0.614906	0.474383	0.460049	0.025*
C3	0.70942 (11)	0.25496 (15)	0.43728 (5)	0.0254 (3)
H3A	0.757906	0.211344	0.467036	0.031*
C4	0.74845 (11)	0.22829 (15)	0.38585 (5)	0.0253 (3)
H4A	0.825281	0.170966	0.380112	0.030*
C5	0.67633 (11)	0.28480 (14)	0.33766 (5)	0.0217 (3)
C6	0.72385 (11)	0.27239 (16)	0.28412 (5)	0.0283 (3)
H6A	0.802888	0.221366	0.278469	0.034*
C7	0.65723 (12)	0.33359 (18)	0.23898 (5)	0.0326 (3)
H7A	0.690314	0.323634	0.202679	0.039*
C8	0.54248 (12)	0.40913 (18)	0.24702 (5)	0.0310 (3)
H8A	0.497589	0.453920	0.216316	0.037*
C9	0.49282 (11)	0.41954 (16)	0.29999 (5)	0.0248 (3)
H9A	0.413361	0.469673	0.305235	0.030*
C10	0.55839 (10)	0.35729 (14)	0.34528 (4)	0.0194 (3)
C11	0.41033 (11)	0.19854 (17)	0.40406 (4)	0.0246 (3)
C12	0.46253 (12)	0.01786 (16)	0.40624 (5)	0.0286 (3)
H12A	0.402026	−0.065651	0.391528	0.043*
H12B	0.481906	−0.012546	0.444707	0.043*
H12C	0.538021	0.012847	0.383922	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0209 (4)	0.0274 (5)	0.0270 (4)	0.0081 (4)	−0.0010 (3)	−0.0028 (3)
O2	0.0353 (5)	0.0279 (5)	0.0180 (4)	−0.0033 (4)	0.0008 (3)	0.0007 (3)
O3	0.0209 (5)	0.0464 (6)	0.0476 (6)	−0.0060 (4)	0.0021 (4)	0.0026 (4)
C1	0.0189 (5)	0.0200 (6)	0.0208 (6)	0.0022 (4)	0.0004 (4)	−0.0005 (4)
C2	0.0230 (6)	0.0207 (5)	0.0192 (5)	0.0001 (4)	−0.0007 (4)	0.0001 (4)
C3	0.0239 (6)	0.0238 (6)	0.0287 (6)	0.0040 (5)	−0.0063 (5)	0.0010 (5)
C4	0.0197 (5)	0.0221 (6)	0.0342 (6)	0.0041 (5)	−0.0001 (5)	−0.0009 (5)
C5	0.0222 (6)	0.0171 (5)	0.0258 (6)	−0.0023 (4)	0.0026 (4)	−0.0019 (4)
C6	0.0271 (6)	0.0262 (6)	0.0316 (6)	−0.0028 (5)	0.0089 (5)	−0.0049 (5)
C7	0.0383 (7)	0.0364 (7)	0.0230 (6)	−0.0114 (6)	0.0086 (5)	−0.0031 (5)
C8	0.0348 (7)	0.0368 (7)	0.0212 (6)	−0.0089 (6)	−0.0027 (5)	0.0040 (5)
C9	0.0234 (6)	0.0270 (6)	0.0242 (6)	−0.0039 (5)	−0.0017 (4)	0.0021 (5)
C10	0.0204 (5)	0.0170 (5)	0.0207 (6)	−0.0034 (4)	0.0007 (4)	−0.0005 (4)
C11	0.0240 (6)	0.0327 (7)	0.0172 (5)	−0.0052 (5)	0.0009 (4)	0.0013 (5)
C12	0.0352 (7)	0.0260 (6)	0.0246 (6)	−0.0093 (5)	−0.0022 (5)	0.0012 (5)

Geometric parameters (Å, º) top

O1—C1	1.4250 (13)	C5—C6	1.3949 (17)
O1—H1O	0.85 (2)	C5—C10	1.4038 (16)
O2—C2	1.4258 (14)	C6—C7	1.3878 (19)
O2—H2O	0.87 (2)	C6—H6A	0.9500
O3—C11	1.2157 (15)	C7—C8	1.3834 (19)
C1—C10	1.5287 (14)	C7—H7A	0.9500
C1—C2	1.5387 (15)	C8—C9	1.3898 (17)
C1—C11	1.5477 (16)	C8—H8A	0.9500
C2—C3	1.4979 (16)	C9—C10	1.3875 (16)
C2—H2A	1.0000	C9—H9A	0.9500
C3—C4	1.3273 (18)	C11—C12	1.4890 (18)
C3—H3A	0.9500	C12—H12A	0.9800
C4—C5	1.4661 (17)	C12—H12B	0.9800
C4—H4A	0.9500	C12—H12C	0.9800

C1—O1—H1O	109.2 (14)	C7—C6—H6A	119.6
C2—O2—H2O	107.7 (12)	C5—C6—H6A	119.6
O1—C1—C10	110.42 (9)	C8—C7—C6	119.78 (11)
O1—C1—C2	106.85 (9)	C8—C7—H7A	120.1
C10—C1—C2	113.59 (9)	C6—C7—H7A	120.1
O1—C1—C11	108.58 (9)	C7—C8—C9	120.04 (11)
C10—C1—C11	106.15 (9)	C7—C8—H8A	120.0
C2—C1—C11	111.19 (9)	C9—C8—H8A	120.0
O2—C2—C3	112.29 (9)	C10—C9—C8	120.51 (11)
O2—C2—C1	107.09 (9)	C10—C9—H9A	119.7
C3—C2—C1	114.66 (9)	C8—C9—H9A	119.7
O2—C2—H2A	107.5	C9—C10—C5	119.81 (10)
C3—C2—H2A	107.5	C9—C10—C1	119.68 (10)
C1—C2—H2A	107.5	C5—C10—C1	120.41 (10)
C4—C3—C2	122.89 (11)	O3—C11—C12	122.53 (12)
C4—C3—H3A	118.6	O3—C11—C1	117.90 (12)
C2—C3—H3A	118.6	C12—C11—C1	119.54 (10)
C3—C4—C5	121.86 (11)	C11—C12—H12A	109.5
C3—C4—H4A	119.1	C11—C12—H12B	109.5
C5—C4—H4A	119.1	H12A—C12—H12B	109.5
C6—C5—C10	118.94 (11)	C11—C12—H12C	109.5
C6—C5—C4	121.28 (11)	H12A—C12—H12C	109.5
C10—C5—C4	119.76 (10)	H12B—C12—H12C	109.5
C7—C6—C5	120.88 (11)

O1—C1—C2—O2	82.61 (10)	C8—C9—C10—C1	−175.77 (11)
C10—C1—C2—O2	−155.38 (9)	C6—C5—C10—C9	−1.80 (16)
C11—C1—C2—O2	−35.72 (12)	C4—C5—C10—C9	176.51 (11)
O1—C1—C2—C3	−152.09 (9)	C6—C5—C10—C1	174.58 (10)
C10—C1—C2—C3	−30.08 (13)	C4—C5—C10—C1	−7.11 (15)
C11—C1—C2—C3	89.58 (11)	O1—C1—C10—C9	−39.09 (14)
O2—C2—C3—C4	143.39 (11)	C2—C1—C10—C9	−159.09 (10)
C1—C2—C3—C4	20.86 (16)	C11—C1—C10—C9	78.42 (12)
C2—C3—C4—C5	−2.66 (18)	O1—C1—C10—C5	144.53 (10)
C3—C4—C5—C6	173.34 (11)	C2—C1—C10—C5	24.52 (14)
C3—C4—C5—C10	−4.93 (17)	C11—C1—C10—C5	−97.96 (11)
C10—C5—C6—C7	1.26 (17)	O1—C1—C11—O3	11.68 (13)
C4—C5—C6—C7	−177.03 (11)	C10—C1—C11—O3	−107.04 (12)
C5—C6—C7—C8	0.46 (19)	C2—C1—C11—O3	128.96 (11)
C6—C7—C8—C9	−1.64 (19)	O1—C1—C11—C12	−170.17 (10)
C7—C8—C9—C10	1.10 (18)	C10—C1—C11—C12	71.11 (12)
C8—C9—C10—C5	0.64 (17)	C2—C1—C11—C12	−52.88 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3	0.85 (2)	2.08 (2)	2.5970 (13)	118.2 (17)
O1—H1O···O3ⁱ	0.85 (2)	2.44 (2)	2.9568 (13)	119.8 (17)
O2—H2O···O1ⁱⁱ	0.87 (2)	1.92 (2)	2.7825 (12)	172.5 (16)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1, −y+1, −z+1.

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