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

Mustafa, A.; Shah, M.R.; Khatoon, M.; Ng, S.W.

doi:10.1107/S1600536809010836

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o912

doi:10.1107/S1600536809010836

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

Asra Mustafa,^a Muhammad Raza Shah,^a Maimoona Khatoon ^a and Seik Weng Ng ^b ^*

^aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 March 2009; accepted 24 March 2009; online 28 March 2009)

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, C 2/c
a = 18.7604 (3) Å
b = 14.3204 (3) Å
c = 10.9997 (2) Å
β = 110.144 (1)°
V = 2774.37 (9) Å³
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[F² > 2σ(F²)] = 0.043
wR(F²) = 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

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) $[x, -y+1, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010836/xu2499sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010836/xu2499Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of C₃₂H₃₄O₆ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₃₂H₃₄O₆	F(000) = 1096
M_r = 514.59	D_x = 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 top

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

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0548P)² + 1.9389P] where P = (F_o² + 2F_c²)/3
3198 reflections	(Δ/σ)_max = 0.001
175 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₂H₃₄O₆	V = 2774.37 (9) Å³
M_r = 514.59	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.7604 (3) Å	µ = 0.08 mm⁻¹
b = 14.3204 (3) Å	T = 133 K
c = 10.9997 (2) Å	0.30 × 0.15 × 0.10 mm
β = 110.144 (1)°

Data collection top

Bruker SMART APEX diffractometer	2514 reflections with I > 2σ(I)
12968 measured reflections	R_int = 0.035
3198 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
3198 reflections	Δρ_min = −0.20 e Å⁻³
175 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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 code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₂H₃₄O₆
M_r	514.59
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	133
a, b, c (Å)	18.7604 (3), 14.3204 (3), 10.9997 (2)
β (°)	110.144 (1)
V (Å³)	2774.37 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12968, 3198, 2514
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.121, 1.01
No. of reflections	3198
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z+1/2.

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

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