Crystal structure of (R)-2′-benz­yloxy-[1,1′-binaphthalen]-2-yl tri­fluoro­methane­sulfonate

Carrilho, R.M.B.; Pereira, M.M.; Maria, T.M.R.; Eusébio, M.E.S.; Rodrigues, V.H.

doi:10.1107/S1600536814019096

organic compounds

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1096-o1097

doi:10.1107/S1600536814019096

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Crystal structure of (R)-2′-benzyloxy-[1,1′-binaphthalen]-2-yl trifluoromethanesulfonate

Rui M. B. Carrilho,^a Mariette M. Pereira,^a Teresa M. R. Maria,^a M. Ermelinda S. Eusébio ^a and V. H. Rodrigues ^b ^*

^aChemistry Department, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal
^*Correspondence e-mail: vhugo@fis.uc.pt

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 August 2014; accepted 22 August 2014; online 10 September 2014)

In the title compound, C₂₈H₁₉F₃O₄S, a new 2′-benzyloxy (R)-BINOL derivative containing a trifluoromethanesulfonate group in the 2-position, the planes of the two naphthyl ring systems (r.m.s. deviations = 0.012 and 0.019 Å) are at an angle of 73.36 (2)°, and the planes of the benzyl ring and the naphthyl ring system bound to the ether O atom are at an angle of 75.67 (4)°. In the crystal, molecules are linked via C—H⋯F hydrogen bonds, forming chains propagating along [100]. The chains are linked via a weak C—F⋯π interaction and weak π–π interactions [shortest inter-centroid distance = 3.9158 (12) Å], forming a three-dimensional structure. The absolute structure of the molecule in the crystal was determined by resonant scattering [Flack parameter = 0.02 (6)].

Keywords: crystal structure; (R)-BINOL; binaphthyl; sulfonate; chiral.

CCDC reference: 1020770

1. Related literature

For the synthesis of some BINOL derivatives, see, for example: Carrilho et al. (2012 , 2014 ). For the synthesis of related binaphthyl-based trifluoromethanesulfonate derivatives, see: Zeng et al. (2011 ); Singer & Buchwald (1999 ); Meškovà et al. (2011 ); Sälinger & Brückner (2009 ); Zheng et al. (2013 ). For the use of aryl trifluoromethanesulfonate derivatives as intermediates in Buchwald–Hartwig aminations, see: Louie et al. (1997 ); Ahman & Buchwald (1997 ); Meadows et al. (2008 ). For a review of the synthesis and catalytic applications of binaphthyl-based phosphine and phosphite ligands, see: Sakai et al. (1993 ); Yan & Zhang (2006 ); Pereira et al. (2013 ).

2. Experimental

2.1. Crystal data

C₂₈H₁₉F₃O₄S
M_r = 508.49
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.3383 (4) Å
b = 12.3380 (5) Å
c = 20.5893 (8) Å
V = 2372.22 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.36 × 0.28 × 0.1 mm

2.1.2. Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.890, T_max = 1.000
42588 measured reflections
5367 independent reflections
4373 reflections with I > 2σ(I)
R_int = 0.038

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.088
S = 1.06
5367 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 )
Absolute structure parameter: 0.02 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C4/C9/C10 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯F3ⁱ	0.93	2.50	3.357 (2)	153
C28—F3⋯Cg1ⁱⁱ	1.29 (1)	3.61 (1)	4.632 (3)	136 (1)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (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: ORTEPII (Johnson, 1976 ) and Mercury (Macrae et al. 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1020770

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814019096/su2775sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019096/su2775Isup2.hkl

checkCIF report

Related literature top

For the synthesis of some BINOL derivatives, see, for example: Carrilho et al. (2012, 2014). For the synthesis of related binaphthyl-based trifluoromethanesulfonate derivatives, see: Zeng et al. (2011); Singer & Buchwald (1999); Meškovà et al. (2011); Sälinger & Brückner (2009); Zheng et al. (2013). For the use of aryl trifluoromethanesulfonate derivatives as intermediates in Buchwald–Hartwig aminations, see: Louie et al. (1997); Ahman & Buchwald (1997); Meadows et al. (2008). For a review of the synthesis and catalytic applications of binaphthyl-based phosphine and phosphite ligands, see: Sakai et al. (1993); Yan & Zhang (2006); Pereira et al. (2013).

Experimental top

The title compound was synthesized from (R)-BINOL according to an optimized two step procedure. To a solution of (R)-BINOL (5.00 g, 17 mmol), dried azeotropically with toluene, triphenylphosphine (PPh3) (4.5 g, 17 mmol) and benzyl alcohol (2.1 ml, 20 mmol), in dry THF (100 ml), diethyl azodicarboxylate (DEAD) (40% in toluene, 7.5 ml, 17 mmol) was added drop wise, at 273 K and the mixture was stirred at 298 K, for 48 h. After quenching with water, the solvent was evaporated under reduced pressure and the crude mixture was dissolved in dichloromethane (50 ml). The organic layer was washed with brine (3 × 50 ml) and water (3 × 50 ml) and dried over anhydrous Na₂SO₄. After removal of the solvent under reduced pressure, the product was isolated by column chromatography on silica gel, using a mixture of CH₂Cl₂/n-hexane (2:1) as eluent, and was further purified by recrystallization from toluene/n-hexane yielding white crystals. The intermediate product, (R)-2'-(benzyloxy)-1,1'-binaphthyl-2-ol (L), with a white crystalline aspect, was obtained in 91% yield (5.85 g, 15.5 mmol). The respective NMR data obtained are in agreement with published values [Takahashi, M. & Ogasawara, K. (1997). Tetrahedron Asymmetry, 8, 3125–3130]. Next, to a solution of (L) (2.82 g, 7.5 mmol) in anhydrous CH₂Cl₂ (15 ml), were added sequentially and drop wise, at 273 K under a nitrogen atmosphere, pyridine (1.0 ml, 12 mmol) and trifluoromethanesulfonic anhydride (triflic anhydride) (1.5 ml, 9 mmol.) The mixture, which produced a red solution, was allowed to warm to room temperature and stirred for 6 h. n-Hexane (20 ml) was then added, and the mixture was passed over a silica gel column (previously activated at 473 K). The silica gel column was washed with 40 ml of a mixture of CH₂Cl₂/n-hexane (1:1). After removal of the solvents under reduced pressure, the title compound was obtained as a white solid in 87% yield (3.30 g, 6.5 mmol). Crystals suitable for X-ray diffraction analysis were obtained after dissolution of the title compound (5 mg ml^-1) in ethyl acetate, and left for the solvent to evaporate in air at room temperature for 48 h.

Spectroscopic data for the title compound: ¹H NMR (CDCl₃, TMS, 400 MHz) δ (p.p.m.) 5.01 (s, 2H, OCH₂Ph), 6.92–6.99 (m, 3H, ArH), 7.03–7.05 (m, 3H, ArH), 7.13 (t, J=7.4 Hz, 1H, ArH), 7.19–7.27 (m, 3H, ArH), 7.29 (d, J=9.2 Hz, 1H, ArH), 7.36–7.40 (m, 1H, ArH), 7.46 (d, J=8.8 Hz, 1H, ArH), 7.73 (d,J=8.0 Hz, 1H, ArH), 7.81–7.86 (m, 2H, ArH), 7.89 (d, J=8.8 Hz, 1H, ArH). ¹³C NMR (CDCl₃, TMS, 100 MHz) δ (p.p.m.) 70.8 (OCH₂Ph), 114.7 (ArC), 116.2 (ArC), 116.8 (CF₃), 119.7 (ArC), 120.0 (ArC), 124.0 (ArC), 125.2 (ArC), 126.7 (ArC), 126.9 (ArC), 127.0 (ArC), 127.1 (ArC), 127.5 (ArC), 127.5 (ArC), 127.6 (ArC), 128.2 (ArC), 128.3 (ArC), 128.4 (ArC), 129.1 (ArC), 130.4 (ArC), 131.1 (ArC), 132.7 (ArC), 133.8 (ArC), 133.8 (ArC), 137.3 (OCH₂C_Ph), 145.8 (COTf), 154.4 (COBn). ¹⁹F NMR (CDCl₃, TFA, 376 MHz) δ (p.p.m.) -73.61 (OS(O)2CF₃). Mp: 128–131 °C.

Computing details top

Data collection: APEX2 (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: ORTEPII (Johnson, 1976) and Mercury (Macrae et al. 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. The C-H···F hydrogen bonds are shown as dashed lines (see Table 1 for details).

(R)-2'-Benzyloxy-[1,1'-binaphthalen]-2-yl trifluoromethanesulfonate top

Crystal data top

C₂₈H₁₉F₃O₄S	F(000) = 1048
M_r = 508.49	D_x = 1.424 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6182 reflections
a = 9.3383 (4) Å	θ = 2.6–22.2°
b = 12.3380 (5) Å	µ = 0.19 mm⁻¹
c = 20.5893 (8) Å	T = 293 K
V = 2372.22 (17) Å³	Prismatic, colourless
Z = 4	0.36 × 0.28 × 0.1 mm

Data collection top

Bruker APEXII diffractometer	5367 independent reflections
Radiation source: fine-focus sealed tube	4373 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→12
T_min = 0.890, T_max = 1.000	k = −15→15
42588 measured reflections	l = −26→26

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0437P)² + 0.1954P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.088	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.18 e Å⁻³
5367 reflections	Δρ_min = −0.24 e Å⁻³
326 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0058 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (6)

Crystal data top

C₂₈H₁₉F₃O₄S	V = 2372.22 (17) Å³
M_r = 508.49	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.3383 (4) Å	µ = 0.19 mm⁻¹
b = 12.3380 (5) Å	T = 293 K
c = 20.5893 (8) Å	0.36 × 0.28 × 0.1 mm

Data collection top

Bruker APEXII diffractometer	5367 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4373 reflections with I > 2σ(I)
T_min = 0.890, T_max = 1.000	R_int = 0.038
42588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.18 e Å⁻³
S = 1.06	Δρ_min = −0.24 e Å⁻³
5367 reflections	Absolute structure: Flack (1983)
326 parameters	Absolute structure parameter: 0.02 (6)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.71125 (5)	0.03924 (4)	0.94675 (2)	0.04816 (14)
O1	0.62251 (12)	0.04090 (10)	1.01056 (5)	0.0417 (3)
O2	0.74153 (18)	−0.06979 (12)	0.93075 (8)	0.0706 (4)
O3	0.81614 (18)	0.12109 (14)	0.94647 (8)	0.0759 (5)
C28	0.5709 (3)	0.08085 (18)	0.89039 (11)	0.0641 (6)
F1	0.46451 (16)	0.01259 (12)	0.89093 (7)	0.0829 (4)
F2	0.6254 (2)	0.08254 (15)	0.83119 (7)	0.1095 (6)
F3	0.5251 (2)	0.17688 (12)	0.90464 (9)	0.1210 (8)
C1	0.66233 (18)	0.11054 (13)	1.06373 (8)	0.0381 (4)
C2	0.5916 (2)	0.20964 (15)	1.06794 (9)	0.0471 (5)
H2	0.5246	0.2301	1.0368	0.056*
C3	0.6231 (2)	0.27570 (16)	1.11882 (10)	0.0533 (5)
H3	0.5767	0.3421	1.1227	0.064*
C4	0.7249 (2)	0.24510 (14)	1.16576 (9)	0.0462 (4)
C5	0.7608 (3)	0.31324 (17)	1.21878 (11)	0.0633 (6)
H5	0.7165	0.3804	1.2229	0.076*
C6	0.8584 (3)	0.2820 (2)	1.26350 (11)	0.0705 (7)
H6	0.8812	0.3281	1.2977	0.085*
C7	0.9252 (3)	0.18142 (19)	1.25880 (10)	0.0664 (6)
H7	0.9915	0.1607	1.2901	0.080*
C8	0.8943 (2)	0.11300 (17)	1.20867 (9)	0.0520 (5)
H8	0.9400	0.0462	1.2061	0.062*
C9	0.7933 (2)	0.14259 (14)	1.16045 (8)	0.0405 (4)
C10	0.76185 (18)	0.07382 (13)	1.10677 (8)	0.0362 (4)
C11	0.83484 (18)	−0.03262 (14)	1.09688 (8)	0.0361 (4)
C12	0.97941 (18)	−0.03635 (14)	1.07440 (8)	0.0368 (4)
C13	1.0607 (2)	0.05821 (15)	1.06183 (9)	0.0473 (4)
H13	1.0190	0.1260	1.0674	0.057*
C14	1.1994 (2)	0.05104 (18)	1.04172 (10)	0.0588 (5)
H14	1.2512	0.1140	1.0337	0.071*
C15	1.2648 (2)	−0.05005 (19)	1.03296 (10)	0.0604 (5)
H15	1.3602	−0.0538	1.0203	0.072*
C16	1.1901 (2)	−0.14184 (17)	1.04285 (9)	0.0500 (5)
H16	1.2341	−0.2085	1.0361	0.060*
C17	1.04466 (19)	−0.13834 (14)	1.06346 (8)	0.0396 (4)
C18	0.9652 (2)	−0.23321 (15)	1.07409 (9)	0.0447 (4)
H18	1.0073	−0.3002	1.0661	0.054*
C19	0.8274 (2)	−0.22913 (14)	1.09589 (9)	0.0438 (4)
H19	0.7767	−0.2929	1.1031	0.053*
C20	0.76214 (18)	−0.12812 (13)	1.10741 (8)	0.0374 (4)
O4	0.62534 (13)	−0.11801 (10)	1.13046 (7)	0.0486 (3)
C21	0.5362 (2)	−0.21227 (16)	1.13402 (10)	0.0506 (5)
H21A	0.5492	−0.2543	1.0946	0.061*
H21B	0.4370	−0.1892	1.1354	0.061*
C22	0.56468 (19)	−0.28464 (15)	1.19158 (9)	0.0432 (4)
C23	0.4871 (2)	−0.37900 (17)	1.19706 (11)	0.0568 (5)
H23	0.4214	−0.3971	1.1649	0.068*
C24	0.5055 (3)	−0.44718 (18)	1.24960 (12)	0.0673 (6)
H24	0.4516	−0.5103	1.2529	0.081*
C25	0.6022 (3)	−0.42192 (19)	1.29639 (11)	0.0657 (6)
H25	0.6146	−0.4678	1.3318	0.079*
C26	0.6814 (3)	−0.32918 (19)	1.29156 (11)	0.0654 (6)
H26	0.7486	−0.3125	1.3233	0.079*
C27	0.6614 (2)	−0.25998 (17)	1.23930 (10)	0.0543 (5)
H27	0.7141	−0.1962	1.2366	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0493 (3)	0.0501 (3)	0.0450 (2)	−0.0092 (2)	0.0044 (2)	−0.0009 (2)
O1	0.0400 (6)	0.0445 (7)	0.0407 (6)	−0.0051 (6)	−0.0015 (5)	0.0028 (6)
O2	0.0793 (10)	0.0590 (9)	0.0736 (10)	0.0117 (8)	0.0072 (8)	−0.0157 (7)
O3	0.0716 (10)	0.0955 (12)	0.0607 (9)	−0.0437 (9)	0.0134 (8)	−0.0032 (8)
C28	0.0933 (17)	0.0476 (12)	0.0513 (12)	−0.0119 (13)	−0.0123 (12)	0.0061 (10)
F1	0.0779 (9)	0.0843 (10)	0.0867 (9)	−0.0169 (8)	−0.0295 (8)	0.0098 (8)
F2	0.1557 (16)	0.1263 (13)	0.0465 (8)	−0.0335 (13)	−0.0093 (9)	0.0187 (8)
F3	0.193 (2)	0.0576 (9)	0.1125 (13)	0.0383 (11)	−0.0741 (14)	−0.0055 (8)
C1	0.0384 (9)	0.0354 (9)	0.0407 (9)	0.0003 (7)	0.0022 (7)	−0.0006 (7)
C2	0.0448 (10)	0.0429 (10)	0.0536 (11)	0.0117 (9)	−0.0018 (9)	0.0086 (9)
C3	0.0568 (12)	0.0395 (11)	0.0636 (13)	0.0160 (9)	0.0064 (10)	−0.0011 (10)
C4	0.0508 (11)	0.0397 (10)	0.0483 (10)	0.0018 (9)	0.0113 (9)	−0.0030 (8)
C5	0.0801 (16)	0.0489 (12)	0.0609 (13)	0.0017 (11)	0.0130 (12)	−0.0143 (10)
C6	0.0911 (18)	0.0670 (15)	0.0535 (13)	−0.0082 (13)	0.0002 (13)	−0.0184 (11)
C7	0.0761 (16)	0.0744 (15)	0.0486 (12)	0.0002 (13)	−0.0097 (11)	−0.0050 (11)
C8	0.0565 (12)	0.0530 (12)	0.0463 (11)	0.0045 (10)	−0.0041 (9)	−0.0009 (9)
C9	0.0447 (10)	0.0388 (9)	0.0380 (9)	−0.0007 (9)	0.0049 (8)	0.0005 (7)
C10	0.0365 (9)	0.0327 (9)	0.0393 (9)	0.0019 (7)	0.0046 (7)	0.0041 (7)
C11	0.0399 (9)	0.0331 (9)	0.0353 (8)	0.0036 (8)	−0.0011 (7)	0.0023 (7)
C12	0.0389 (9)	0.0370 (9)	0.0345 (8)	0.0014 (8)	−0.0021 (7)	0.0011 (7)
C13	0.0462 (10)	0.0406 (10)	0.0552 (11)	−0.0012 (8)	0.0039 (9)	0.0038 (9)
C14	0.0498 (11)	0.0572 (13)	0.0693 (13)	−0.0108 (11)	0.0071 (10)	0.0057 (10)
C15	0.0407 (10)	0.0726 (15)	0.0679 (13)	0.0028 (11)	0.0122 (9)	0.0018 (11)
C16	0.0450 (11)	0.0527 (12)	0.0524 (11)	0.0110 (9)	0.0071 (9)	−0.0003 (9)
C17	0.0437 (10)	0.0406 (10)	0.0344 (9)	0.0073 (8)	−0.0009 (7)	0.0004 (7)
C18	0.0529 (11)	0.0366 (10)	0.0444 (10)	0.0082 (9)	0.0008 (8)	−0.0018 (8)
C19	0.0525 (11)	0.0326 (10)	0.0463 (10)	−0.0011 (8)	0.0007 (8)	0.0026 (8)
C20	0.0372 (9)	0.0352 (9)	0.0398 (9)	0.0027 (7)	0.0010 (7)	0.0048 (7)
O4	0.0422 (7)	0.0387 (7)	0.0651 (8)	−0.0009 (6)	0.0113 (6)	0.0073 (6)
C21	0.0425 (10)	0.0474 (11)	0.0618 (12)	−0.0080 (9)	−0.0027 (9)	0.0084 (9)
C22	0.0368 (10)	0.0425 (10)	0.0502 (10)	−0.0028 (8)	0.0053 (8)	0.0012 (8)
C23	0.0567 (13)	0.0494 (12)	0.0643 (13)	−0.0165 (10)	0.0002 (10)	0.0014 (10)
C24	0.0769 (15)	0.0464 (12)	0.0785 (15)	−0.0107 (12)	0.0119 (13)	0.0092 (12)
C25	0.0802 (16)	0.0589 (14)	0.0580 (13)	0.0100 (13)	0.0094 (12)	0.0137 (11)
C26	0.0714 (15)	0.0728 (15)	0.0520 (12)	−0.0009 (13)	−0.0048 (11)	0.0065 (11)
C27	0.0580 (12)	0.0529 (12)	0.0521 (11)	−0.0130 (10)	−0.0019 (10)	0.0029 (9)

Geometric parameters (Å, º) top

S1—O3	1.4069 (15)	C13—C14	1.362 (3)
S1—O2	1.4136 (15)	C13—H13	0.9300
S1—O1	1.5535 (12)	C14—C15	1.400 (3)
S1—C28	1.824 (2)	C14—H14	0.9300
O1—C1	1.440 (2)	C15—C16	1.346 (3)
C28—F3	1.293 (3)	C15—H15	0.9300
C28—F1	1.302 (3)	C16—C17	1.423 (3)
C28—F2	1.321 (3)	C16—H16	0.9300
C1—C10	1.362 (2)	C17—C18	1.403 (3)
C1—C2	1.393 (2)	C18—C19	1.363 (3)
C2—C3	1.360 (3)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.407 (2)
C3—C4	1.407 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—O4	1.368 (2)
C4—C5	1.418 (3)	O4—C21	1.432 (2)
C4—C9	1.421 (2)	C21—C22	1.508 (3)
C5—C6	1.352 (3)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—C7	1.392 (3)	C22—C27	1.369 (3)
C6—H6	0.9300	C22—C23	1.376 (3)
C7—C8	1.364 (3)	C23—C24	1.381 (3)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.417 (3)	C24—C25	1.357 (3)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.424 (2)	C25—C26	1.366 (3)
C10—C11	1.493 (2)	C25—H25	0.9300
C11—C20	1.377 (2)	C26—C27	1.386 (3)
C11—C12	1.428 (2)	C26—H26	0.9300
C12—C13	1.416 (3)	C27—H27	0.9300
C12—C17	1.416 (2)

O3—S1—O2	122.88 (11)	C14—C13—C12	120.78 (18)
O3—S1—O1	111.42 (8)	C14—C13—H13	119.6
O2—S1—O1	108.45 (9)	C12—C13—H13	119.6
O3—S1—C28	107.20 (11)	C13—C14—C15	120.76 (19)
O2—S1—C28	105.27 (11)	C13—C14—H14	119.6
O1—S1—C28	98.69 (10)	C15—C14—H14	119.6
C1—O1—S1	120.87 (10)	C16—C15—C14	120.26 (17)
F3—C28—F1	109.8 (2)	C16—C15—H15	119.9
F3—C28—F2	108.80 (19)	C14—C15—H15	119.9
F1—C28—F2	108.19 (19)	C15—C16—C17	120.95 (18)
F3—C28—S1	110.54 (16)	C15—C16—H16	119.5
F1—C28—S1	111.13 (14)	C17—C16—H16	119.5
F2—C28—S1	108.3 (2)	C18—C17—C12	119.26 (16)
C10—C1—C2	125.14 (16)	C18—C17—C16	121.73 (16)
C10—C1—O1	118.18 (14)	C12—C17—C16	119.00 (17)
C2—C1—O1	116.65 (15)	C19—C18—C17	121.32 (17)
C3—C2—C1	118.13 (17)	C19—C18—H18	119.3
C3—C2—H2	120.9	C17—C18—H18	119.3
C1—C2—H2	120.9	C18—C19—C20	119.78 (17)
C2—C3—C4	120.98 (17)	C18—C19—H19	120.1
C2—C3—H3	119.5	C20—C19—H19	120.1
C4—C3—H3	119.5	O4—C20—C11	115.90 (14)
C3—C4—C5	121.96 (18)	O4—C20—C19	122.91 (15)
C3—C4—C9	119.32 (17)	C11—C20—C19	121.18 (16)
C5—C4—C9	118.71 (19)	C20—O4—C21	119.09 (14)
C6—C5—C4	121.0 (2)	O4—C21—C22	114.75 (16)
C6—C5—H5	119.5	O4—C21—H21A	108.6
C4—C5—H5	119.5	C22—C21—H21A	108.6
C5—C6—C7	120.6 (2)	O4—C21—H21B	108.6
C5—C6—H6	119.7	C22—C21—H21B	108.6
C7—C6—H6	119.7	H21A—C21—H21B	107.6
C8—C7—C6	120.6 (2)	C27—C22—C23	118.46 (18)
C8—C7—H7	119.7	C27—C22—C21	123.30 (17)
C6—C7—H7	119.7	C23—C22—C21	118.22 (17)
C7—C8—C9	120.77 (19)	C22—C23—C24	121.0 (2)
C7—C8—H8	119.6	C22—C23—H23	119.5
C9—C8—H8	119.6	C24—C23—H23	119.5
C8—C9—C4	118.34 (16)	C25—C24—C23	119.9 (2)
C8—C9—C10	121.85 (16)	C25—C24—H24	120.0
C4—C9—C10	119.80 (16)	C23—C24—H24	120.0
C1—C10—C9	116.60 (15)	C24—C25—C26	120.1 (2)
C1—C10—C11	121.02 (15)	C24—C25—H25	120.0
C9—C10—C11	122.37 (15)	C26—C25—H25	120.0
C20—C11—C12	119.31 (16)	C25—C26—C27	120.0 (2)
C20—C11—C10	120.39 (14)	C25—C26—H26	120.0
C12—C11—C10	120.27 (16)	C27—C26—H26	120.0
C13—C12—C17	118.19 (15)	C22—C27—C26	120.6 (2)
C13—C12—C11	122.66 (16)	C22—C27—H27	119.7
C17—C12—C11	119.15 (16)	C26—C27—H27	119.7

O3—S1—O1—C1	−7.53 (15)	C1—C10—C11—C12	104.50 (19)
O2—S1—O1—C1	130.68 (13)	C9—C10—C11—C12	−74.6 (2)
C28—S1—O1—C1	−119.94 (13)	C20—C11—C12—C13	179.35 (16)
O3—S1—C28—F3	−53.6 (2)	C10—C11—C12—C13	1.3 (2)
O2—S1—C28—F3	174.03 (18)	C20—C11—C12—C17	0.0 (2)
O1—S1—C28—F3	62.1 (2)	C10—C11—C12—C17	−178.01 (14)
O3—S1—C28—F1	−175.81 (17)	C17—C12—C13—C14	−2.0 (3)
O2—S1—C28—F1	51.9 (2)	C11—C12—C13—C14	178.62 (18)
O1—S1—C28—F1	−60.08 (18)	C12—C13—C14—C15	0.0 (3)
O3—S1—C28—F2	65.48 (18)	C13—C14—C15—C16	1.6 (3)
O2—S1—C28—F2	−66.86 (17)	C14—C15—C16—C17	−1.2 (3)
O1—S1—C28—F2	−178.79 (15)	C13—C12—C17—C18	−178.51 (17)
S1—O1—C1—C10	−85.42 (17)	C11—C12—C17—C18	0.9 (2)
S1—O1—C1—C2	96.53 (17)	C13—C12—C17—C16	2.4 (2)
C10—C1—C2—C3	−0.1 (3)	C11—C12—C17—C16	−178.21 (16)
O1—C1—C2—C3	177.79 (17)	C15—C16—C17—C18	−179.92 (19)
C1—C2—C3—C4	0.3 (3)	C15—C16—C17—C12	−0.9 (3)
C2—C3—C4—C5	179.2 (2)	C12—C17—C18—C19	−1.2 (3)
C2—C3—C4—C9	−1.3 (3)	C16—C17—C18—C19	177.82 (18)
C3—C4—C5—C6	179.7 (2)	C17—C18—C19—C20	0.7 (3)
C9—C4—C5—C6	0.2 (3)	C12—C11—C20—O4	178.43 (15)
C4—C5—C6—C7	−0.6 (4)	C10—C11—C20—O4	−3.6 (2)
C5—C6—C7—C8	0.6 (4)	C12—C11—C20—C19	−0.5 (2)
C6—C7—C8—C9	−0.2 (4)	C10—C11—C20—C19	177.46 (16)
C7—C8—C9—C4	−0.2 (3)	C18—C19—C20—O4	−178.70 (16)
C7—C8—C9—C10	178.4 (2)	C18—C19—C20—C11	0.2 (3)
C3—C4—C9—C8	−179.31 (18)	C11—C20—O4—C21	171.35 (15)
C5—C4—C9—C8	0.2 (3)	C19—C20—O4—C21	−9.7 (2)
C3—C4—C9—C10	2.1 (3)	C20—O4—C21—C22	79.1 (2)
C5—C4—C9—C10	−178.42 (17)	O4—C21—C22—C27	3.9 (3)
C2—C1—C10—C9	0.9 (3)	O4—C21—C22—C23	−177.56 (17)
O1—C1—C10—C9	−177.00 (14)	C27—C22—C23—C24	0.4 (3)
C2—C1—C10—C11	−178.24 (16)	C21—C22—C23—C24	−178.2 (2)
O1—C1—C10—C11	3.9 (2)	C22—C23—C24—C25	−0.7 (4)
C8—C9—C10—C1	179.60 (17)	C23—C24—C25—C26	0.0 (4)
C4—C9—C10—C1	−1.8 (2)	C24—C25—C26—C27	0.9 (4)
C8—C9—C10—C11	−1.3 (3)	C23—C22—C27—C26	0.6 (3)
C4—C9—C10—C11	177.27 (16)	C21—C22—C27—C26	179.1 (2)
C1—C10—C11—C20	−73.5 (2)	C25—C26—C27—C22	−1.3 (3)
C9—C10—C11—C20	107.46 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1-C4/C9/C10 ring

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···F3ⁱ	0.93	2.50	3.357 (2)	153
C28—F3···Cg1ⁱⁱ	1.29 (1)	3.61 (1)	4.632 (3)	136 (1)

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1-C4/C9/C10 ring

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···F3ⁱ	0.93	2.50	3.357 (2)	153
C28—F3···Cg1ⁱⁱ	1.293 (3)	3.613 (2)	4.632 (3)	136.0 (2)

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

Acknowledgements

This work was supported by funds from FEDER via the COMPETE (Programa Operacional Factores de Competitividade) programme and by the FCT (Fundação para a Ciência e a Tecnologia) (project PEst-C/FIS/UI0036/2011).

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Volume 70| Part 10| October 2014| Pages o1096-o1097

doi:10.1107/S1600536814019096

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (R)-2′-benz­yl­oxy-[1,1′-binaphthalen]-2-yl tri­fluoro­methane­sulfonate

1. Related literature

2. Experimental

2.1. Crystal data

2.1.2. Data collection

2.1.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (R)-2′-benzyloxy-[1,1′-binaphthalen]-2-yl trifluoromethanesulfonate