(1S,2S)-2-[(S)-2,2,2-Tri­fluoro-1-hy­droxy­eth­yl]-1-tetra­lol

Radan, K.; Cotman, A.E.; Lozinšek, M.

doi:10.1107/S2414314623002171

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 3| March 2023| x230217

https://doi.org/10.1107/S2414314623002171

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(1S,2S)-2-[(S)-2,2,2-Trifluoro-1-hydroxyethyl]-1-tetralol

Kristian Radan,^a Andrej Emanuel Cotman ^b and Matic Lozinšek ^a ^*

^aDepartment of Inorganic Chemistry and Technology, Jožef Stefan Institute, Jamova cesta 39, 1000 Ljubljana, Slovenia, and ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ljubljana, Aškerceva cesta 7, 1000 Ljubljana, Slovenia
^*Correspondence e-mail: matic.lozinsek@ijs.si

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 3 March 2023; accepted 7 March 2023; online 15 March 2023)

The crystal structure of the title enantiopure tetralol derivative {systematic name: (1S,2S)-2-[(S)-2,2,2-trifluoro-1-hydroxyethyl]-1,2,3,4-tetrahydronaphthalen-1-ol}, C₁₂H₁₃F₃O₂, synthesized by asymmetric transfer hydrogenation, was elucidated by low-temperature single-crystal X-ray diffraction. The enantiopure compound crystallizes in the Sohncke space group P2₁2₁2₁ with one molecule in the asymmetric unit and features intramolecular as well as intermolecular O—H⋯O hydrogen bonding. The absolute configuration was established from anomalous dispersion effects.

Keywords: tetralol; crystal structure; asymmetric transfer hydrogenation; trifluoromethyl group.

CCDC reference: 2246795

Structure description

Homochiral fluorinated alcohols, which are considered to be emerging structural motifs in medicinal chemistry (Cotman, 2021 ), can be obtained in high yields employing dynamic kinetic resolution (DKR) with Noyori–Ikariya asymmetric transfer hydrogenation (ATH) (Betancourt et al., 2021 ; Cotman et al. 2022 ; Molina Betancourt et al., 2022 ). When Ru^II-catalyzed DKR–ATH was applied to CF₃CO-substituted benzofused cyclic ketones, it was observed that single or double reduction occurs, yielding either diastereo- and enantiopure monoalcohols or 1,3-diols (Cotman et al., 2016 ). The crystal structure of the mono-reduced product (S)-2-[(S)-2,2,2-trifluoro-1-hydroxyethyl]-1-tetralone has been described previously (Motaln et al., 2023 ) and herein the crystal structure of the corresponding diol is presented.

(1S,2S)-2-[(S)-2,2,2-Trifluoro-1-hydroxyethyl]-1-tetralol crystallizes in the orthorhombic P2₁2₁2₁ space group with one molecule in the asymmetric unit (Fig. 1). The cyclohexanol ring adopts a half-chair conformation (Cremer & Pople, 1975 ), with the C2 atom located 0.251 (3) Å below and the C3 atom 0.497 (4) Å above the plane defined by atoms C1, C4, C5, and C10 (r.m.s.d. of 0.013 Å). This plane is essentially coplanar with the aromatic ring – the angle between the plane normals is 2.79 (9)° and the r.m.s. deviation of the plane defined by all coplanar atoms C1, C4–C10 is 0.025 Å. Tetralol derivatives with similar half-chair conformations have been reported, for example, 2,2,2-trifluoro-N-(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (CSD refcode ALUXUC; Miyazawa et al., 2016 ), (1S,2S)-7-methoxy-2-(trifluoromethyl)-1-tetralol (YEDBOC; Cotman et al., 2022), and plastically flexible (1R,2S)-2-(trifluoromethylthio)-1-tetralol (YEDCAP; Cotman et al., 2022).

Figure 1
Molecular structure of (1S,2S)-2-[(S)-2,2,2-trifluoro-1-hydroxyethyl]-1-tetralol showing the atom-labeling scheme. Thermal displacement ellipsoids are drawn at the 50% probability level and the hydrogen atoms are shown as spheres of arbitrary radius.

In the crystal of the title compound, intramolecular and intermolecular O—H⋯O hydrogen bonds with O⋯O distances of 2.854 (2) and 2.789 (2) Å, respectively, link adjacent molecules related by the 2₁ screw axis, into chains parallel to [010] (Table 1 and Figs. 2 and 3). The graph-set motifs of the hydrogen bonds are S(6) and C(6) (Etter et al., 1990 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.83 (4)	2.23 (4)	2.854 (2)	133 (3)
O2—H2⋯O1ⁱ	0.94 (4)	1.87 (4)	2.789 (2)	168 (3)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Helical hydrogen-bonded chain extending parallel to [010] that involves intermolecular and intramolecular O—H⋯O hydrogen bonds, which are indicated by blue dashed lines.

Figure 3
Molecular packing of the title compound viewed along [010]. The helical hydrogen-bonded chains are shown by blue dashed lines.

Synthesis and crystallization

The title compound was prepared from 2-trifluoroacetyl-1-tetralone (100 mg, 0.412 mmol) added to a HCO₂H/Et₃N 3:2 (0.21 ml) solution containing the active (S,S)-diphenylethylenediamine-based Ru^II catalyst with an S/C ratio of 1000:1 (Cotman et al., 2016). Upon addition of the co-solvent chlorobenzene (0.55 ml), the mixture was warmed to 60 °C and stirred for 24 h, while being continuously flushed with N₂. The resulting mixture was partitioned between EtOAc (10 ml) and H₂O (5 ml), with the organic layer later washed with H₂O (5 ml) and brine (5 ml), filtered through a bed of silica gel/Na₂SO₄, and concentrated. The crude product was recrystallized from a 5:1 mixture of petroleum ether and diethyl ether affording colorless prisms (37 mg; 36% yield; diastereomeric ratio 97:3:0:0; enantiomeric excess >99.9%). A suitable crystal was selected under a polarizing microscope and attached to a MiTeGen Dual Thickness MicroLoop using Baysilone-Paste (Bayer-Silicone, mittelviskos) as the adhesive.

Refinement

The crystal data, data collection, and structure refinement details are summarized in Table 2. The positions of the hydrogen atoms and their isotropic displacement parameter U were freely refined (Cooper et al., 2010 ). The absolute configuration was established as S,S,S for C1, C2, and C11, respectively, based on anomalous dispersion effects [Flack x = 0.06 (5); Hooft y = 0.07 (3)] (Parsons et al., 2013 ; Hooft et al., 2008 ).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₃F₃O₂
M_r	246.22
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.75558 (10), 9.02843 (10), 15.5656 (2)
V (Å³)	1089.92 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.17
Crystal size (mm)	0.08 × 0.07 × 0.06

Data collection
Diffractometer	XtaLAB Synergy-S, Dualflex, Eiger2 R CdTe 1M
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2022 )
T_min, T_max	0.886, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	38720, 2273, 2255
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.073, 1.06
No. of reflections	2273
No. of parameters	207
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.17
Absolute structure	Flack x determined using 929 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.06 (5)
Computer programs: CrysAlis PRO (Rigaku OD, 2022), OLEX2.solve (Dolomanov et al., 2009 ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009), DIAMOND (Brandenburg, 2005 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2246795

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623002171/tk4089sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623002171/tk4089Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314623002171/tk4089Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: olex2.solve (Dolomanov et al., 2009); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009), DIAMOND (Brandenburg, 2005); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009), publCIF (Westrip, 2010).

(1S,2S)-2-[(S)-2,2,2-Trifluoro-1-hydroxyethyl]-1,2,3,4-tetrahydronaphthalen-1-ol top

Crystal data top

C₁₂H₁₃F₃O₂	D_x = 1.501 Mg m⁻³
M_r = 246.22	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 29238 reflections
a = 7.75558 (10) Å	θ = 2.9–75.7°
b = 9.02843 (10) Å	µ = 1.17 mm⁻¹
c = 15.5656 (2) Å	T = 100 K
V = 1089.92 (2) Å³	Cube, colourless
Z = 4	0.08 × 0.07 × 0.06 mm
F(000) = 512

Data collection top

XtaLAB Synergy-S, Dualflex, Eiger2 R CdTe 1M diffractometer	2273 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2255 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.053
Detector resolution: 13.3333 pixels mm^-1	θ_max = 76.1°, θ_min = 5.7°
ω scans	h = −9→8
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	k = −11→11
T_min = 0.886, T_max = 1.000	l = −19→19
38720 measured reflections

Refinement top

Refinement on F²	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0325P)² + 0.4546P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.029	(Δ/σ)_max < 0.001
wR(F²) = 0.073	Δρ_max = 0.35 e Å⁻³
S = 1.06	Δρ_min = −0.17 e Å⁻³
2273 reflections	Extinction correction: SHELXL-2019/2 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
207 parameters	Extinction coefficient: 0.0016 (4)
0 restraints	Absolute structure: Flack x determined using 929 quotients [(I⁺)–(I^–)]/[(I⁺)+(I^–)] (Parsons et al., 2013)
Primary atom site location: iterative	Absolute structure parameter: 0.06 (5)
Hydrogen site location: difference Fourier map

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.

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

	x	y	z	U_iso*/U_eq
F3	0.80337 (19)	0.85568 (15)	0.60230 (9)	0.0345 (3)
F1	0.69235 (19)	0.72956 (16)	0.49867 (9)	0.0322 (3)
O2	0.49295 (19)	0.76829 (16)	0.65842 (10)	0.0237 (3)
F2	0.89287 (17)	0.63500 (16)	0.57649 (10)	0.0355 (4)
O1	0.38269 (19)	0.51110 (16)	0.74976 (9)	0.0198 (3)
C5	0.3786 (3)	0.2240 (2)	0.61093 (12)	0.0179 (4)
C1	0.3588 (2)	0.4939 (2)	0.65812 (12)	0.0171 (4)
C10	0.2838 (3)	0.3406 (2)	0.64639 (12)	0.0178 (4)
C12	0.7506 (3)	0.7194 (2)	0.57933 (14)	0.0248 (5)
C4	0.5590 (3)	0.2478 (2)	0.57692 (13)	0.0203 (4)
C11	0.6192 (3)	0.6587 (2)	0.64276 (13)	0.0201 (4)
C9	0.1166 (3)	0.3148 (2)	0.67633 (14)	0.0211 (4)
C8	0.0440 (3)	0.1739 (3)	0.67329 (14)	0.0243 (4)
C3	0.6458 (3)	0.3820 (2)	0.61755 (13)	0.0196 (4)
C7	0.1391 (3)	0.0578 (2)	0.63868 (14)	0.0239 (4)
C2	0.5296 (2)	0.5175 (2)	0.60927 (13)	0.0178 (4)
C6	0.3043 (3)	0.0827 (2)	0.60742 (13)	0.0212 (4)
H11	0.680 (4)	0.646 (3)	0.6961 (16)	0.025 (7)*
H6	0.369 (3)	−0.005 (3)	0.5850 (16)	0.024 (6)*
H9	0.055 (4)	0.395 (3)	0.6995 (17)	0.028 (7)*
H8	−0.071 (4)	0.156 (3)	0.6950 (17)	0.031 (7)*
H3A	0.666 (3)	0.359 (3)	0.6794 (16)	0.023 (6)*
H1A	0.277 (3)	0.570 (3)	0.6402 (15)	0.015 (5)*
H4A	0.553 (4)	0.266 (3)	0.5136 (17)	0.029 (7)*
H2A	0.498 (3)	0.534 (3)	0.5494 (16)	0.022 (6)*
H4B	0.623 (3)	0.155 (3)	0.5878 (17)	0.029 (7)*
H7	0.094 (4)	−0.037 (3)	0.6371 (18)	0.031 (7)*
H3B	0.757 (3)	0.401 (3)	0.5896 (17)	0.024 (6)*
H1	0.415 (4)	0.598 (4)	0.755 (2)	0.053 (10)*
H2	0.549 (5)	0.848 (4)	0.685 (2)	0.059 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F3	0.0359 (7)	0.0259 (7)	0.0418 (7)	−0.0144 (6)	0.0096 (6)	−0.0073 (6)
F1	0.0371 (7)	0.0326 (7)	0.0271 (6)	−0.0095 (6)	0.0025 (6)	0.0059 (5)
O2	0.0221 (7)	0.0175 (7)	0.0314 (8)	0.0003 (6)	0.0003 (6)	−0.0025 (6)
F2	0.0200 (6)	0.0358 (8)	0.0507 (8)	−0.0024 (6)	0.0095 (6)	0.0009 (6)
O1	0.0238 (7)	0.0168 (7)	0.0189 (7)	−0.0023 (6)	0.0006 (6)	−0.0005 (6)
C5	0.0196 (9)	0.0172 (9)	0.0170 (8)	0.0007 (8)	−0.0039 (8)	0.0016 (7)
C1	0.0167 (9)	0.0158 (8)	0.0187 (9)	0.0013 (8)	−0.0009 (7)	−0.0002 (7)
C10	0.0180 (9)	0.0169 (9)	0.0184 (8)	0.0001 (8)	−0.0029 (7)	0.0025 (7)
C12	0.0261 (11)	0.0212 (10)	0.0273 (10)	−0.0053 (8)	0.0028 (8)	−0.0042 (8)
C4	0.0203 (10)	0.0178 (9)	0.0230 (10)	0.0025 (7)	0.0034 (8)	−0.0008 (8)
C11	0.0192 (9)	0.0181 (9)	0.0230 (9)	−0.0007 (8)	0.0010 (8)	−0.0015 (8)
C9	0.0178 (9)	0.0218 (10)	0.0236 (9)	0.0006 (8)	−0.0016 (8)	0.0010 (8)
C8	0.0186 (10)	0.0270 (10)	0.0273 (10)	−0.0064 (8)	−0.0037 (8)	0.0050 (9)
C3	0.0155 (8)	0.0211 (9)	0.0222 (9)	0.0006 (7)	0.0017 (8)	−0.0002 (8)
C7	0.0262 (11)	0.0189 (10)	0.0267 (10)	−0.0067 (8)	−0.0090 (9)	0.0023 (8)
C2	0.0180 (9)	0.0163 (8)	0.0192 (9)	−0.0014 (7)	0.0001 (8)	−0.0005 (7)
C6	0.0258 (10)	0.0169 (9)	0.0207 (9)	−0.0003 (8)	−0.0053 (8)	0.0010 (8)

Geometric parameters (Å, º) top

F3—C12	1.345 (2)	C4—H4A	1.00 (3)
F1—C12	1.338 (3)	C4—H4B	0.99 (3)
O2—C11	1.413 (2)	C11—C2	1.542 (3)
O2—H2	0.94 (4)	C11—H11	0.96 (3)
F2—C12	1.342 (3)	C9—C8	1.392 (3)
O1—C1	1.447 (2)	C9—H9	0.94 (3)
O1—H1	0.83 (4)	C8—C7	1.390 (3)
C5—C10	1.398 (3)	C8—H8	0.96 (3)
C5—C4	1.511 (3)	C3—C2	1.525 (3)
C5—C6	1.401 (3)	C3—H3A	1.00 (3)
C1—C10	1.512 (3)	C3—H3B	0.98 (3)
C1—C2	1.542 (3)	C7—C6	1.389 (3)
C1—H1A	0.98 (2)	C7—H7	0.93 (3)
C10—C9	1.397 (3)	C2—H2A	0.98 (3)
C12—C11	1.522 (3)	C6—H6	1.00 (3)
C4—C3	1.524 (3)

C11—O2—H2	107 (2)	O2—C11—H11	106.0 (16)
C1—O1—H1	103 (2)	C12—C11—C2	112.35 (17)
C10—C5—C4	121.21 (17)	C12—C11—H11	105.9 (16)
C10—C5—C6	119.02 (18)	C2—C11—H11	114.5 (17)
C6—C5—C4	119.76 (18)	C10—C9—H9	117.8 (17)
O1—C1—C10	105.47 (15)	C8—C9—C10	121.10 (19)
O1—C1—C2	111.18 (15)	C8—C9—H9	121.1 (17)
O1—C1—H1A	106.8 (14)	C9—C8—H8	120.9 (17)
C10—C1—C2	113.45 (16)	C7—C8—C9	119.2 (2)
C10—C1—H1A	111.3 (14)	C7—C8—H8	119.9 (17)
C2—C1—H1A	108.5 (14)	C4—C3—C2	110.02 (16)
C5—C10—C1	122.30 (17)	C4—C3—H3A	107.8 (16)
C9—C10—C5	119.60 (18)	C4—C3—H3B	110.2 (15)
C9—C10—C1	118.03 (17)	C2—C3—H3A	110.1 (15)
F3—C12—C11	111.16 (18)	C2—C3—H3B	109.8 (15)
F1—C12—F3	106.85 (18)	H3A—C3—H3B	109 (2)
F1—C12—F2	106.60 (18)	C8—C7—H7	120.7 (17)
F1—C12—C11	114.03 (18)	C6—C7—C8	120.20 (19)
F2—C12—F3	106.17 (17)	C6—C7—H7	119.1 (17)
F2—C12—C11	111.57 (18)	C1—C2—C11	109.55 (16)
C5—C4—C3	112.12 (16)	C1—C2—H2A	105.9 (15)
C5—C4—H4A	109.0 (16)	C11—C2—H2A	108.1 (15)
C5—C4—H4B	106.6 (16)	C3—C2—C1	110.76 (16)
C3—C4—H4A	107.5 (16)	C3—C2—C11	111.62 (16)
C3—C4—H4B	112.4 (16)	C3—C2—H2A	110.7 (15)
H4A—C4—H4B	109 (2)	C5—C6—H6	121.9 (14)
O2—C11—C12	108.89 (16)	C7—C6—C5	120.86 (19)
O2—C11—C2	108.96 (16)	C7—C6—H6	117.2 (14)

F3—C12—C11—O2	47.8 (2)	C10—C1—C2—C11	−165.55 (16)
F3—C12—C11—C2	168.61 (17)	C10—C1—C2—C3	−42.0 (2)
F1—C12—C11—O2	−73.1 (2)	C10—C9—C8—C7	−0.9 (3)
F1—C12—C11—C2	47.8 (2)	C12—C11—C2—C1	−159.85 (17)
O2—C11—C2—C1	−39.1 (2)	C12—C11—C2—C3	77.1 (2)
O2—C11—C2—C3	−162.14 (16)	C4—C5—C10—C1	−4.0 (3)
F2—C12—C11—O2	166.11 (16)	C4—C5—C10—C9	179.31 (17)
F2—C12—C11—C2	−73.1 (2)	C4—C5—C6—C7	179.64 (17)
O1—C1—C10—C5	−108.6 (2)	C4—C3—C2—C1	62.5 (2)
O1—C1—C10—C9	68.1 (2)	C4—C3—C2—C11	−175.18 (16)
O1—C1—C2—C11	−46.9 (2)	C9—C8—C7—C6	−0.1 (3)
O1—C1—C2—C3	76.7 (2)	C8—C7—C6—C5	0.7 (3)
C5—C10—C9—C8	1.5 (3)	C2—C1—C10—C5	13.3 (3)
C5—C4—C3—C2	−52.3 (2)	C2—C1—C10—C9	−169.99 (17)
C1—C10—C9—C8	−175.33 (19)	C6—C5—C10—C1	175.72 (17)
C10—C5—C4—C3	23.6 (3)	C6—C5—C10—C9	−1.0 (3)
C10—C5—C6—C7	−0.1 (3)	C6—C5—C4—C3	−156.10 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.83 (4)	2.23 (4)	2.854 (2)	133 (3)
O2—H2···O1ⁱ	0.94 (4)	1.87 (4)	2.789 (2)	168 (3)

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Funding information

Funding for this research was provided by: European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant No. 950625); Jožef Stefan Institute Director's Fund; Slovenian Research Agency (grant No. P1-0208).

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