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Acta Cryst. (2009). E65, o911    [ doi:10.1107/S1600536809010824 ]

Dimethyl (1,1'-binaphthyl-2,2'-dioxy)diacetate

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

Abstract top

The two naphthyl fused-ring systems in the title compound, C22H26O6, are aligned at 86.7 (1)°. Weak intermolecular C-H...O hydrogen bonding is present in the crystal structure.

Related literature top

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

Experimental top

Potassium carbonate (0.55 g, 4 mmol) and 1,1'-binaphthyl-2,2'-diol (0.29 mg, 1 mmol) in acetone (10 ml) were stirred for 15 minutes. Methyl 2-chloroacetate (0.54 g, 10 mmol) was added and the mixture was stirred at 323 K for 24twenty-four hours. The solvent was removed and the residue was dissolved in a mixture of water (25 ml) and dichloromethane (25 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 recrystallized from dichloromethane (0.33 g, 80% yield).

Refinement top

The crystal did not diffract strongly. To lower the observeds:parameters ratio, the fused rings were refined as rigid naphthalenes of 1.39 Å sides.

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 Uiso(H) set to 1.2 to 1.5Ueq(C).

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
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of C26H22O6 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Dimethyl (1,1'-binaphthyl-2,2'-dioxy)diacetate top
Crystal data top
C26H22O6F(000) = 1808
Mr = 430.44Dx = 1.358 Mg m−3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 1966 reflections
a = 17.1288 (5) Åθ = 2.3–21.8°
b = 29.439 (1) ŵ = 0.10 mm−1
c = 8.3518 (3) ÅT = 123 K
V = 4211.5 (3) Å3Prism, colorless
Z = 80.27 × 0.12 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		2613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
graphiteθmax = 25.0°, θmin = 1.4°
ω scansh = −19→20
17329 measured reflectionsk = −35→34
3700 independent reflectionsl = −9→9
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.085H-atom parameters constrained
wR(F2) = 0.195 w = 1/[σ2(Fo2) + (0.05P)2 + 9P]
where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max = 0.001
3700 reflectionsΔρmax = 0.57 e Å−3
244 parametersΔρmin = −0.50 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0039 (6)
Crystal data top
C26H22O6V = 4211.5 (3) Å3
Mr = 430.44Z = 8
Orthorhombic, PccnMo Kα radiation
a = 17.1288 (5) ŵ = 0.10 mm−1
b = 29.439 (1) ÅT = 123 K
c = 8.3518 (3) Å0.27 × 0.12 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		2613 reflections with I > 2σ(I)
17329 measured reflectionsRint = 0.069
3700 independent reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.085H-atom parameters constrained
wR(F2) = 0.195Δρmax = 0.57 e Å−3
S = 1.23Δρmin = −0.50 e Å−3
3700 reflectionsAbsolute structure: ?
244 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.49537 (14)0.44569 (9)0.6224 (3)0.0253 (7)
O20.41229 (16)0.50497 (10)0.9571 (4)0.0349 (8)
O30.43431 (17)0.43116 (9)0.9055 (4)0.0334 (7)
O40.56053 (15)0.38327 (10)0.2796 (4)0.0331 (7)
O50.75115 (16)0.41527 (10)0.1635 (4)0.0367 (8)
O60.67299 (16)0.44878 (10)0.3437 (4)0.0351 (8)
C10.44243 (9)0.38011 (6)0.4970 (3)0.0247 (9)
C20.43217 (11)0.42447 (6)0.5501 (3)0.0232 (9)
C30.36353 (12)0.44760 (5)0.5150 (3)0.0260 (9)
H30.35650.47790.55120.031*
C40.30515 (10)0.42638 (5)0.4268 (3)0.0293 (10)
H40.25820.44220.40280.035*
C50.31541 (8)0.38203 (5)0.3738 (2)0.0289 (10)
C60.38405 (8)0.35890 (5)0.4089 (2)0.0267 (9)
C70.39431 (11)0.31454 (5)0.3558 (3)0.0370 (11)
H70.44120.29870.37980.044*
C80.33593 (14)0.29333 (6)0.2677 (3)0.0478 (13)
H80.34290.26300.23140.057*
C90.26729 (13)0.31646 (7)0.2326 (3)0.0453 (13)
H90.22740.30200.17230.054*
C100.25703 (10)0.36081 (7)0.2856 (3)0.0366 (11)
H100.21010.37660.26160.044*
C110.52100 (10)0.35656 (7)0.5345 (2)0.0251 (9)
C120.57926 (12)0.36020 (7)0.4193 (2)0.0278 (10)
C130.65175 (11)0.34032 (8)0.4455 (2)0.0334 (11)
H130.69160.34280.36680.040*
C140.66599 (9)0.31681 (7)0.5869 (3)0.0342 (11)
H140.71550.30320.60480.041*
C150.60774 (9)0.31317 (5)0.7020 (2)0.0304 (10)
C160.53524 (8)0.33305 (5)0.6758 (2)0.0281 (10)
C170.47698 (10)0.32941 (8)0.7910 (2)0.0365 (11)
H170.42740.34300.77310.044*
C180.49122 (14)0.30589 (8)0.9323 (2)0.0446 (13)
H180.45140.30341.01100.054*
C190.56372 (15)0.28602 (8)0.9585 (2)0.0493 (14)
H190.57340.26991.05510.059*
C200.62197 (12)0.28966 (7)0.8434 (2)0.0426 (12)
H200.67150.27610.86130.051*
C210.4810 (2)0.48465 (13)0.7182 (5)0.0251 (9)
H21A0.45020.50670.65470.030*
H21B0.53160.49910.74440.030*
C220.4379 (2)0.47498 (14)0.8724 (5)0.0277 (10)
C230.4005 (3)0.41876 (16)1.0604 (5)0.0378 (11)
H23A0.38380.38691.05770.057*
H23B0.35530.43821.08250.057*
H23C0.43970.42291.14470.057*
C240.6217 (2)0.39136 (15)0.1669 (5)0.0312 (10)
H24A0.59970.40560.06940.037*
H24B0.64570.36210.13580.037*
C250.6833 (2)0.42214 (14)0.2373 (5)0.0279 (10)
C260.8161 (3)0.44240 (17)0.2228 (6)0.0441 (13)
H26A0.80580.47460.20200.066*
H26B0.86420.43330.16810.066*
H26C0.82190.43760.33830.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0193 (13)0.0271 (15)0.0295 (17)0.0006 (11)0.0016 (12)−0.0053 (13)
O20.0353 (16)0.0398 (17)0.0297 (18)0.0082 (14)0.0038 (14)−0.0048 (15)
O30.0429 (17)0.0302 (16)0.0271 (17)−0.0061 (13)0.0034 (14)0.0016 (14)
O40.0216 (14)0.0433 (18)0.0346 (18)0.0013 (12)0.0041 (13)0.0074 (15)
O50.0238 (14)0.0423 (17)0.044 (2)−0.0057 (13)0.0102 (14)−0.0114 (16)
O60.0338 (16)0.0358 (17)0.0356 (18)0.0062 (13)0.0020 (14)−0.0068 (16)
C10.022 (2)0.025 (2)0.027 (2)0.0001 (16)0.0015 (17)0.0037 (19)
C20.0209 (19)0.028 (2)0.020 (2)−0.0054 (16)0.0017 (17)0.0017 (18)
C30.023 (2)0.029 (2)0.025 (2)0.0010 (17)0.0026 (17)0.0002 (19)
C40.020 (2)0.036 (2)0.031 (2)0.0028 (17)0.0018 (18)0.009 (2)
C50.022 (2)0.036 (2)0.029 (2)−0.0070 (17)−0.0004 (18)0.009 (2)
C60.026 (2)0.027 (2)0.027 (2)−0.0061 (16)0.0037 (18)0.0028 (19)
C70.031 (2)0.035 (2)0.045 (3)−0.0047 (19)−0.005 (2)0.002 (2)
C80.045 (3)0.033 (3)0.065 (4)−0.015 (2)−0.005 (3)0.000 (3)
C90.038 (3)0.045 (3)0.053 (3)−0.021 (2)−0.011 (2)0.004 (3)
C100.025 (2)0.043 (3)0.043 (3)−0.0110 (19)−0.002 (2)0.012 (2)
C110.023 (2)0.022 (2)0.030 (2)−0.0037 (16)−0.0040 (18)−0.0036 (19)
C120.025 (2)0.024 (2)0.034 (3)−0.0029 (16)−0.0050 (19)−0.001 (2)
C130.022 (2)0.029 (2)0.049 (3)−0.0001 (17)0.000 (2)−0.006 (2)
C140.025 (2)0.021 (2)0.056 (3)0.0032 (17)−0.011 (2)−0.003 (2)
C150.031 (2)0.020 (2)0.041 (3)0.0019 (17)−0.012 (2)−0.003 (2)
C160.029 (2)0.021 (2)0.034 (3)−0.0037 (16)−0.0042 (19)0.000 (2)
C170.040 (3)0.028 (2)0.042 (3)0.0017 (19)−0.003 (2)0.005 (2)
C180.056 (3)0.035 (3)0.043 (3)0.002 (2)0.002 (2)0.011 (2)
C190.069 (4)0.028 (2)0.051 (3)0.003 (2)−0.020 (3)0.008 (2)
C200.043 (3)0.027 (2)0.058 (3)0.005 (2)−0.015 (3)−0.005 (2)
C210.026 (2)0.022 (2)0.027 (2)−0.0015 (16)0.0001 (18)−0.0026 (18)
C220.023 (2)0.034 (2)0.026 (2)0.0006 (17)−0.0042 (18)−0.001 (2)
C230.039 (3)0.044 (3)0.030 (3)−0.010 (2)0.000 (2)0.006 (2)
C240.026 (2)0.036 (2)0.032 (3)0.0001 (17)0.0076 (19)−0.002 (2)
C250.030 (2)0.025 (2)0.029 (2)0.0056 (17)0.0039 (19)0.003 (2)
C260.032 (2)0.053 (3)0.046 (3)−0.011 (2)0.002 (2)−0.007 (3)
Geometric parameters (Å, °) top
O1—C21.388 (3)C11—C161.3900
O1—C211.420 (5)C12—C131.3900
O2—C221.213 (5)C13—C141.3900
O3—C221.321 (5)C13—H130.9500
O3—C231.464 (5)C14—C151.3900
O4—C121.388 (3)C14—H140.9500
O4—C241.428 (5)C15—C161.3900
O5—C251.330 (5)C15—C201.3900
O5—C261.456 (5)C16—C171.3900
O6—C251.199 (5)C17—C181.3900
C1—C21.3900C17—H170.9500
C1—C61.3900C18—C191.3900
C2—C31.3900C18—H180.9500
C3—C41.3900C19—C201.3900
C3—H30.9500C19—H190.9500
C4—C51.3900C20—H200.9500
C4—H40.9500C21—C221.511 (6)
C5—C61.3900C21—H21A0.9900
C5—C101.3900C21—H21B0.9900
C6—C71.3900C23—H23A0.9800
C7—C81.3900C23—H23B0.9800
C7—H70.9500C23—H23C0.9800
C8—C91.3900C24—C251.511 (6)
C8—H80.9500C24—H24A0.9900
C9—C101.3900C24—H24B0.9900
C9—H90.9500C26—H26A0.9800
C10—H100.9500C26—H26B0.9800
C11—C121.3900C26—H26C0.9800
C2—O1—C21118.3 (2)C17—C16—C15120.0
C22—O3—C23116.5 (3)C17—C16—C11120.0
C12—O4—C24117.8 (3)C15—C16—C11120.0
C25—O5—C26115.2 (3)C16—C17—C18120.0
C2—C1—C6120.0C16—C17—H17120.0
O1—C2—C1117.57 (16)C18—C17—H17120.0
O1—C2—C3122.06 (16)C19—C18—C17120.0
C1—C2—C3120.0C19—C18—H18120.0
C4—C3—C2120.0C17—C18—H18120.0
C4—C3—H3120.0C18—C19—C20120.0
C2—C3—H3120.0C18—C19—H19120.0
C3—C4—C5120.0C20—C19—H19120.0
C3—C4—H4120.0C19—C20—C15120.0
C5—C4—H4120.0C19—C20—H20120.0
C6—C5—C4120.0C15—C20—H20120.0
C6—C5—C10120.0O1—C21—C22114.4 (3)
C4—C5—C10120.0O1—C21—H21A108.7
C7—C6—C5120.0C22—C21—H21A108.7
C7—C6—C1120.0O1—C21—H21B108.7
C5—C6—C1120.0C22—C21—H21B108.7
C8—C7—C6120.0H21A—C21—H21B107.6
C8—C7—H7120.0O2—C22—O3124.9 (4)
C6—C7—H7120.0O2—C22—C21122.4 (4)
C7—C8—C9120.0O3—C22—C21112.6 (3)
C7—C8—H8120.0O3—C23—H23A109.5
C9—C8—H8120.0O3—C23—H23B109.5
C10—C9—C8120.0H23A—C23—H23B109.5
C10—C9—H9120.0O3—C23—H23C109.5
C8—C9—H9120.0H23A—C23—H23C109.5
C9—C10—C5120.0H23B—C23—H23C109.5
C9—C10—H10120.0O4—C24—C25110.9 (4)
C5—C10—H10120.0O4—C24—H24A109.5
C12—C11—C16120.0C25—C24—H24A109.5
O4—C12—C13123.01 (16)O4—C24—H24B109.5
O4—C12—C11116.98 (16)C25—C24—H24B109.5
C13—C12—C11120.0H24A—C24—H24B108.0
C12—C13—C14120.0O6—C25—O5124.9 (4)
C12—C13—H13120.0O6—C25—C24125.3 (4)
C14—C13—H13120.0O5—C25—C24109.8 (4)
C15—C14—C13120.0O5—C26—H26A109.5
C15—C14—H14120.0O5—C26—H26B109.5
C13—C14—H14120.0H26A—C26—H26B109.5
C14—C15—C16120.0O5—C26—H26C109.5
C14—C15—C20120.0H26A—C26—H26C109.5
C16—C15—C20120.0H26B—C26—H26C109.5
C21—O1—C2—C1−161.7 (2)C11—C12—C13—C140.0
C21—O1—C2—C325.3 (4)C12—C13—C14—C150.0
C6—C1—C2—O1−173.2 (2)C13—C14—C15—C160.0
C6—C1—C2—C30.0C13—C14—C15—C20180.0
O1—C2—C3—C4172.9 (2)C14—C15—C16—C17180.0
C1—C2—C3—C40.0C20—C15—C16—C170.0
C2—C3—C4—C50.0C14—C15—C16—C110.0
C3—C4—C5—C60.0C20—C15—C16—C11180.0
C3—C4—C5—C10180.0C12—C11—C16—C17180.0
C4—C5—C6—C7180.0C12—C11—C16—C150.0
C10—C5—C6—C70.0C15—C16—C17—C180.0
C4—C5—C6—C10.0C11—C16—C17—C18180.0
C10—C5—C6—C1180.0C16—C17—C18—C190.0
C2—C1—C6—C7180.0C17—C18—C19—C200.0
C2—C1—C6—C50.0C18—C19—C20—C150.0
C5—C6—C7—C80.0C14—C15—C20—C19180.0
C1—C6—C7—C8180.0C16—C15—C20—C190.0
C6—C7—C8—C90.0C2—O1—C21—C2268.8 (4)
C7—C8—C9—C100.0C23—O3—C22—O2−3.5 (6)
C8—C9—C10—C50.0C23—O3—C22—C21174.1 (3)
C6—C5—C10—C90.0O1—C21—C22—O2−170.2 (4)
C4—C5—C10—C9180.0O1—C21—C22—O312.1 (5)
C24—O4—C12—C13−7.6 (4)C12—O4—C24—C25−64.1 (4)
C24—O4—C12—C11173.8 (2)C26—O5—C25—O61.1 (6)
C16—C11—C12—O4178.6 (2)C26—O5—C25—C24−178.8 (4)
C16—C11—C12—C130.0O4—C24—C25—O6−24.5 (6)
O4—C12—C13—C14−178.5 (2)O4—C24—C25—O5155.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O6i0.952.383.330 (3)174
C21—H21A···O6i0.992.483.326 (5)143
C26—H26B···O1ii0.982.463.338 (6)149
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O6i0.952.383.330 (3)174
C21—H21A···O6i0.992.483.326 (5)143
C26—H26B···O1ii0.982.463.338 (6)149
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y, z−1/2.
Acknowledgements top

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

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.

Wu, Y.-M., Cao, G.-Q., Qian, M.-Y. & Zhu, H.-J. (2007). Acta Cryst. E63, o3446.