Di-tert-butyl (1,1′-binaphthyl-2,2′-di­oxy)diacetate

Abstract

In the crystal structure of the title compound, C₃₂H₃₄O₆, the mol­ecule is located on a twofold rotation axis. The two naphthyl fused-ring systems are aligned at 72.6 (1)°. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the crystal structure of the parent carboxylic acid, see: Wu et al. (2007 ▶).

Experimental

Crystal data

• C₃₂H₃₄O₆

• M _r = 514.59

• Monoclinic,

• a = 18.7604 (3) Å

• b = 14.3204 (3) Å

• c = 10.9997 (2) Å

• β = 110.144 (1)°

• V = 2774.37 (9) ų

• Z = 4

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 133 K

• 0.30 × 0.15 × 0.10 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: none

• 12968 measured reflections

• 3198 independent reflections

• 2514 reflections with I > 2σ(I)

• R _int = 0.035

Refinement

• R[F ² > 2σ(F ²)] = 0.043

• wR(F ²) = 0.121

• S = 1.01

• 3198 reflections

• 175 parameters

• H-atom parameters constrained

• Δρ_max = 0.30 e Å⁻³

• Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2i	0.95	2.38	3.226 (2)	149

Symmetry code: (i) .

supplementary crystallographic information

Experimental

Potassium carbonate (0.97 g, 7 mmol) and 1,1'-binaphthyl-2,2'-diol (0.57 mg, 2 mmol) in acetone (20 ml) were stirred for 15 minutes. tert-Butyl 2-bromoacetate (1.95 g, 10 mmol) was added and the mixture was stirred at 323 K for 2 h. The solvent was removed and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The two phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried and the solvent evaporated. The residue was dissolved recrysstallized from dichloromethane (0.82 mg, 80% yield).

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) plot of C32H34O6 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C32H34O6	F(000) = 1096
Mr = 514.59	Dx = 1.232 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3672 reflections
a = 18.7604 (3) Å	θ = 2.3–28.2°
b = 14.3204 (3) Å	µ = 0.08 mm−1
c = 10.9997 (2) Å	T = 133 K
β = 110.144 (1)°	Block, colorless
V = 2774.37 (9) Å3	0.30 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer	2514 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −24→24
12968 measured reflections	k = −18→18
3198 independent reflections	l = −14→14

Refinement

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0548P)2 + 1.9389P] where P = (Fo2 + 2Fc2)/3
3198 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.38962 (5)	0.53557 (7)	0.23963 (9)	0.0278 (2)
O2	0.28361 (6)	0.45195 (10)	0.03634 (11)	0.0531 (4)
O3	0.19998 (5)	0.45848 (7)	0.14254 (9)	0.0292 (2)
C1	0.49788 (7)	0.63074 (9)	0.31656 (11)	0.0219 (3)
C2	0.55167 (7)	0.68166 (9)	0.41843 (12)	0.0255 (3)
C3	0.61052 (8)	0.73495 (10)	0.39965 (14)	0.0326 (3)
H3	0.6162	0.7352	0.3171	0.039*
C4	0.65937 (10)	0.78615 (12)	0.49836 (16)	0.0441 (4)
H4	0.6980	0.8223	0.4833	0.053*
C5	0.65281 (11)	0.78558 (13)	0.62268 (16)	0.0503 (5)
H5	0.6869	0.8213	0.6908	0.060*
C6	0.59820 (10)	0.73436 (12)	0.64444 (15)	0.0437 (4)
H6	0.5948	0.7336	0.7286	0.052*
C7	0.54571 (8)	0.68154 (10)	0.54431 (13)	0.0314 (3)
C8	0.48693 (8)	0.62974 (12)	0.56391 (13)	0.0350 (3)
H8	0.4833	0.6283	0.6479	0.042*
C9	0.43514 (8)	0.58162 (11)	0.46649 (13)	0.0310 (3)
H9	0.3958	0.5474	0.4824	0.037*
C10	0.44042 (7)	0.58301 (9)	0.34153 (12)	0.0242 (3)
C11	0.32140 (7)	0.50678 (11)	0.25672 (13)	0.0291 (3)
H11A	0.2979	0.5603	0.2857	0.035*
H11B	0.3324	0.4575	0.3238	0.035*
C12	0.26778 (8)	0.46984 (10)	0.13024 (14)	0.0304 (3)
C13	0.13800 (8)	0.40721 (10)	0.04369 (14)	0.0315 (3)
C14	0.16385 (11)	0.30839 (13)	0.0342 (2)	0.0556 (5)
H14A	0.1856	0.2817	0.1213	0.083*
H14B	0.2023	0.3087	−0.0075	0.083*
H14C	0.1204	0.2706	−0.0173	0.083*
C15	0.11375 (9)	0.45879 (14)	−0.08469 (15)	0.0439 (4)
H15A	0.1028	0.5241	−0.0710	0.066*
H15B	0.0681	0.4294	−0.1451	0.066*
H15C	0.1547	0.4562	−0.1208	0.066*
C16	0.07523 (8)	0.40965 (12)	0.10104 (15)	0.0394 (4)
H16A	0.0930	0.3799	0.1865	0.059*
H16B	0.0308	0.3760	0.0440	0.059*
H16C	0.0613	0.4746	0.1097	0.059*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0218 (5)	0.0396 (6)	0.0254 (5)	−0.0038 (4)	0.0123 (4)	−0.0006 (4)
O2	0.0342 (6)	0.0883 (10)	0.0461 (7)	−0.0154 (6)	0.0255 (5)	−0.0245 (6)
O3	0.0220 (5)	0.0364 (5)	0.0321 (5)	−0.0025 (4)	0.0131 (4)	−0.0021 (4)
C1	0.0220 (6)	0.0255 (6)	0.0194 (6)	0.0059 (5)	0.0088 (5)	0.0020 (5)
C2	0.0265 (7)	0.0256 (6)	0.0225 (6)	0.0064 (5)	0.0062 (5)	−0.0007 (5)
C3	0.0345 (7)	0.0302 (7)	0.0292 (7)	−0.0021 (6)	0.0061 (6)	−0.0016 (6)
C4	0.0416 (9)	0.0373 (8)	0.0456 (9)	−0.0091 (7)	0.0050 (7)	−0.0067 (7)
C5	0.0545 (10)	0.0477 (10)	0.0339 (8)	−0.0049 (8)	−0.0037 (8)	−0.0146 (7)
C6	0.0508 (10)	0.0487 (9)	0.0261 (7)	0.0031 (8)	0.0060 (7)	−0.0089 (7)
C7	0.0340 (7)	0.0357 (7)	0.0214 (6)	0.0105 (6)	0.0054 (6)	−0.0029 (5)
C8	0.0367 (8)	0.0513 (9)	0.0199 (6)	0.0129 (7)	0.0134 (6)	0.0035 (6)
C9	0.0282 (7)	0.0447 (8)	0.0241 (7)	0.0072 (6)	0.0142 (6)	0.0064 (6)
C10	0.0218 (6)	0.0310 (7)	0.0213 (6)	0.0062 (5)	0.0094 (5)	0.0035 (5)
C11	0.0223 (6)	0.0385 (8)	0.0310 (7)	0.0016 (5)	0.0150 (6)	0.0050 (6)
C12	0.0249 (7)	0.0345 (7)	0.0359 (7)	−0.0004 (6)	0.0157 (6)	−0.0007 (6)
C13	0.0240 (6)	0.0332 (7)	0.0377 (8)	−0.0051 (6)	0.0110 (6)	−0.0043 (6)
C14	0.0443 (10)	0.0366 (9)	0.0848 (14)	−0.0032 (8)	0.0207 (10)	−0.0131 (9)
C15	0.0359 (8)	0.0621 (11)	0.0335 (8)	−0.0065 (8)	0.0118 (7)	0.0006 (7)
C16	0.0262 (7)	0.0516 (10)	0.0419 (9)	−0.0063 (7)	0.0138 (6)	0.0024 (7)

Geometric parameters (Å, °)

O1—C10	1.3749 (16)	C8—C9	1.360 (2)
O1—C11	1.4174 (15)	C8—H8	0.9500
O2—C12	1.1966 (17)	C9—C10	1.4118 (17)
O3—C12	1.3347 (15)	C9—H9	0.9500
O3—C13	1.4842 (16)	C11—C12	1.504 (2)
C1—C10	1.3815 (17)	C11—H11A	0.9900
C1—C2	1.4237 (18)	C11—H11B	0.9900
C1—C1i	1.494 (2)	C13—C14	1.511 (2)
C2—C3	1.415 (2)	C13—C16	1.5158 (19)
C2—C7	1.4270 (18)	C13—C15	1.518 (2)
C3—C4	1.368 (2)	C14—H14A	0.9800
C3—H3	0.9500	C14—H14B	0.9800
C4—C5	1.415 (2)	C14—H14C	0.9800
C4—H4	0.9500	C15—H15A	0.9800
C5—C6	1.347 (3)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
C6—C7	1.417 (2)	C16—H16A	0.9800
C6—H6	0.9500	C16—H16B	0.9800
C7—C8	1.406 (2)	C16—H16C	0.9800
C10—O1—C11	116.08 (10)	O1—C11—H11A	109.9
C12—O3—C13	121.30 (11)	C12—C11—H11A	109.9
C10—C1—C2	119.15 (11)	O1—C11—H11B	109.9
C10—C1—C1i	120.24 (12)	C12—C11—H11B	109.9
C2—C1—C1i	120.60 (12)	H11A—C11—H11B	108.3
C3—C2—C1	122.59 (12)	O2—C12—O3	126.15 (14)
C3—C2—C7	117.92 (13)	O2—C12—C11	126.00 (13)
C1—C2—C7	119.47 (12)	O3—C12—C11	107.83 (11)
C4—C3—C2	121.09 (14)	O3—C13—C14	108.95 (12)
C4—C3—H3	119.5	O3—C13—C16	102.04 (11)
C2—C3—H3	119.5	C14—C13—C16	111.35 (14)
C3—C4—C5	120.45 (16)	O3—C13—C15	110.43 (12)
C3—C4—H4	119.8	C14—C13—C15	113.09 (15)
C5—C4—H4	119.8	C16—C13—C15	110.43 (13)
C6—C5—C4	119.97 (15)	C13—C14—H14A	109.5
C6—C5—H5	120.0	C13—C14—H14B	109.5
C4—C5—H5	120.0	H14A—C14—H14B	109.5
C5—C6—C7	121.34 (15)	C13—C14—H14C	109.5
C5—C6—H6	119.3	H14A—C14—H14C	109.5
C7—C6—H6	119.3	H14B—C14—H14C	109.5
C8—C7—C6	122.29 (13)	C13—C15—H15A	109.5
C8—C7—C2	118.50 (13)	C13—C15—H15B	109.5
C6—C7—C2	119.20 (14)	H15A—C15—H15B	109.5
C9—C8—C7	122.11 (12)	C13—C15—H15C	109.5
C9—C8—H8	118.9	H15A—C15—H15C	109.5
C7—C8—H8	118.9	H15B—C15—H15C	109.5
C8—C9—C10	119.30 (13)	C13—C16—H16A	109.5
C8—C9—H9	120.3	C13—C16—H16B	109.5
C10—C9—H9	120.3	H16A—C16—H16B	109.5
O1—C10—C1	116.85 (10)	C13—C16—H16C	109.5
O1—C10—C9	121.70 (12)	H16A—C16—H16C	109.5
C1—C10—C9	121.44 (12)	H16B—C16—H16C	109.5
O1—C11—C12	109.05 (10)
C10—C1—C2—C3	−177.72 (12)	C7—C8—C9—C10	0.3 (2)
C1i—C1—C2—C3	0.71 (18)	C11—O1—C10—C1	−164.92 (11)
C10—C1—C2—C7	0.70 (18)	C11—O1—C10—C9	16.29 (18)
C1i—C1—C2—C7	179.14 (11)	C2—C1—C10—O1	179.49 (11)
C1—C2—C3—C4	177.29 (13)	C1i—C1—C10—O1	1.05 (16)
C7—C2—C3—C4	−1.2 (2)	C2—C1—C10—C9	−1.72 (19)
C2—C3—C4—C5	1.1 (2)	C1i—C1—C10—C9	179.83 (11)
C3—C4—C5—C6	0.0 (3)	C8—C9—C10—O1	179.96 (12)
C4—C5—C6—C7	−1.0 (3)	C8—C9—C10—C1	1.2 (2)
C5—C6—C7—C8	−178.13 (16)	C10—O1—C11—C12	171.26 (11)
C5—C6—C7—C2	0.9 (2)	C13—O3—C12—O2	9.7 (2)
C3—C2—C7—C8	179.26 (13)	C13—O3—C12—C11	−168.85 (11)
C1—C2—C7—C8	0.76 (19)	O1—C11—C12—O2	12.1 (2)
C3—C2—C7—C6	0.2 (2)	O1—C11—C12—O3	−169.43 (11)
C1—C2—C7—C6	−178.34 (13)	C12—O3—C13—C14	60.23 (17)
C6—C7—C8—C9	177.77 (14)	C12—O3—C13—C16	178.05 (13)
C2—C7—C8—C9	−1.3 (2)	C12—O3—C13—C15	−64.54 (16)

Symmetry codes: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2ii	0.95	2.38	3.226 (2)	149

Symmetry codes: (ii) x, −y+1, z+1/2.