Di-tert-butyl (1,1'-binaphthyl-2,2'-di-oxy)diacetate.

In the crystal structure of the title compound, C(32)H(34)O(6), the mol-ecule 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 = 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) 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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.01

3198 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −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 ▶).

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

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

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

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

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 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

	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*

	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)

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)

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

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) .