Biphenyl-2,2′-diyl diacetate

Hu, C.-H.; Chen, J.; Quan, J.-C; Wang, J.-T

doi:10.1107/S1600536808035113

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2248

doi:10.1107/S1600536808035113

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Biphenyl-2,2′-diyl diacetate

Chen-Hui Hu,^a Jing Chen,^a ^* Ji-Cai Quan ^a and Jin-Tang Wang ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: cj1908@126.com

(Received 27 October 2008; accepted 28 October 2008; online 8 November 2008)

In the title compound, C₁₆H₁₄O₄, a derivative of 2,2′-biphenol, the benzene rings are oriented at a dihedral angle of 58.32 (3)°.

Related literature

For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₄O₄
M_r = 270.27
Monoclinic, P 2₁ /n
a = 8.8380 (18) Å
b = 18.204 (4) Å
c = 8.9620 (18) Å
β = 108.75 (3)°
V = 1365.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.972, T_max = 0.991
2643 measured reflections
2478 independent reflections
1645 reflections with I > 2σ(I)
R_int = 0.026
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.156
S = 1.00
2478 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035113/hk2562sup1.cif

Structure factors: contains datablock x. DOI: 10.1107/S1600536808035113/hk2562Isup2.hkl

checkCIF report

Comment top

Some derivatives of andrographolide are important chemical materials. We report herein the crystal structure of the title compound.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C3-C8) and B (C9-C14) are, of course, planar and the dihedral angle between them is A/B = 58.32 (3)°.

Related literature top

For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 2,2'-biphenol (10 g) was dissolved in acetic anhydride (50 ml) at room temperature. After the reaction completed, it was extracted with ethyl acetate, washed with saturated salt water and dryed with sodium sulfate. The product was filtrated, and the organic layer was concentrated. Crystals suitable for X-ray analysis were obtained from ethyl acetate (10 ml) at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids drawn at the 30% probability level.

Biphenyl-2,2'-diyl diacetate top

Crystal data top

C₁₆H₁₄O₄	F(000) = 568
M_r = 270.27	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.8380 (18) Å	θ = 9–14°
b = 18.204 (4) Å	µ = 0.10 mm⁻¹
c = 8.9620 (18) Å	T = 294 K
β = 108.75 (3)°	Block, colorless
V = 1365.3 (5) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1645 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 25.3°, θ_min = 2.2°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→21
T_min = 0.972, T_max = 0.991	l = −10→10
2643 measured reflections	3 standard reflections every 120 min
2478 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.04P)² + 2.02P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2478 reflections	Δρ_max = 0.23 e Å⁻³
184 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (3)

Crystal data top

C₁₆H₁₄O₄	V = 1365.3 (5) Å³
M_r = 270.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.8380 (18) Å	µ = 0.10 mm⁻¹
b = 18.204 (4) Å	T = 294 K
c = 8.9620 (18) Å	0.30 × 0.20 × 0.10 mm
β = 108.75 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1645 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.026
T_min = 0.972, T_max = 0.991	3 standard reflections every 120 min
2643 measured reflections	intensity decay: 1%
2478 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
2478 reflections	Δρ_min = −0.27 e Å⁻³
184 parameters

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
O1	0.0543 (3)	0.18629 (18)	0.4765 (3)	0.0742 (8)
O2	0.0736 (3)	0.22040 (12)	0.7226 (3)	0.0486 (6)
O3	0.2528 (3)	0.08431 (13)	0.7691 (2)	0.0468 (6)
O4	0.1896 (4)	−0.03274 (15)	0.7923 (3)	0.0762 (9)
C1	0.2647 (5)	0.2666 (2)	0.6182 (5)	0.0750 (13)
H1A	0.2874	0.2719	0.5209	0.113*
H1B	0.3539	0.2437	0.6952	0.113*
H1C	0.2463	0.3142	0.6553	0.113*
C2	0.1200 (5)	0.2203 (2)	0.5920 (5)	0.0544 (9)
C3	−0.0585 (4)	0.17726 (18)	0.7219 (4)	0.0438 (8)
C4	−0.2080 (4)	0.1915 (2)	0.6172 (4)	0.0576 (10)
H4A	−0.2217	0.2269	0.5392	0.069*
C5	−0.3376 (4)	0.1522 (2)	0.6297 (5)	0.0649 (11)
H5A	−0.4391	0.1613	0.5596	0.078*
C6	−0.3171 (5)	0.1001 (2)	0.7448 (5)	0.0656 (11)
H6A	−0.4047	0.0738	0.7520	0.079*
C7	−0.1664 (4)	0.0864 (2)	0.8507 (4)	0.0522 (9)
H7A	−0.1541	0.0511	0.9287	0.063*
C8	−0.0327 (4)	0.12500 (18)	0.8416 (4)	0.0406 (8)
C9	0.1255 (4)	0.11569 (17)	0.9635 (4)	0.0395 (7)
C10	0.1422 (4)	0.12691 (18)	1.1210 (4)	0.0466 (8)
H10A	0.0525	0.1371	1.1502	0.056*
C11	0.2908 (4)	0.1231 (2)	1.2353 (4)	0.0546 (9)
H11A	0.3003	0.1321	1.3401	0.065*
C12	0.4247 (4)	0.1062 (2)	1.1957 (4)	0.0547 (9)
H12A	0.5242	0.1039	1.2732	0.066*
C13	0.4108 (4)	0.09252 (19)	1.0405 (4)	0.0512 (9)
H13A	0.5005	0.0806	1.0126	0.061*
C14	0.2620 (4)	0.09669 (17)	0.9267 (4)	0.0418 (8)
C15	0.2136 (4)	0.0154 (2)	0.7134 (4)	0.0475 (8)
C16	0.2087 (5)	0.0091 (2)	0.5468 (4)	0.0636 (11)
H16A	0.1746	−0.0395	0.5088	0.095*
H16B	0.3134	0.0180	0.5400	0.095*
H16C	0.1351	0.0445	0.4839	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0705 (19)	0.099 (2)	0.0555 (17)	−0.0022 (17)	0.0229 (14)	−0.0038 (16)
O2	0.0470 (13)	0.0506 (14)	0.0484 (13)	−0.0043 (11)	0.0156 (11)	0.0034 (11)
O3	0.0520 (14)	0.0505 (14)	0.0426 (13)	0.0022 (11)	0.0217 (11)	−0.0004 (11)
O4	0.117 (3)	0.0578 (17)	0.0618 (17)	−0.0175 (17)	0.0403 (17)	−0.0039 (14)
C1	0.069 (3)	0.081 (3)	0.083 (3)	−0.009 (2)	0.034 (2)	0.013 (2)
C2	0.056 (2)	0.056 (2)	0.050 (2)	0.0067 (18)	0.0175 (18)	0.0116 (18)
C3	0.0397 (18)	0.0448 (19)	0.0473 (19)	0.0003 (15)	0.0147 (15)	−0.0042 (15)
C4	0.054 (2)	0.063 (2)	0.051 (2)	0.0104 (19)	0.0100 (18)	−0.0078 (18)
C5	0.040 (2)	0.085 (3)	0.064 (3)	0.009 (2)	0.0099 (18)	−0.016 (2)
C6	0.047 (2)	0.085 (3)	0.071 (3)	−0.012 (2)	0.026 (2)	−0.025 (2)
C7	0.048 (2)	0.060 (2)	0.054 (2)	−0.0084 (17)	0.0233 (17)	−0.0084 (17)
C8	0.0348 (17)	0.0478 (19)	0.0421 (18)	0.0007 (14)	0.0163 (14)	−0.0056 (15)
C9	0.0432 (18)	0.0389 (18)	0.0394 (17)	−0.0009 (14)	0.0172 (14)	0.0023 (14)
C10	0.0465 (19)	0.053 (2)	0.0437 (19)	0.0001 (16)	0.0189 (16)	−0.0018 (15)
C11	0.064 (2)	0.060 (2)	0.0405 (19)	0.0014 (19)	0.0183 (18)	−0.0020 (17)
C12	0.046 (2)	0.063 (2)	0.050 (2)	0.0075 (17)	0.0078 (17)	0.0027 (17)
C13	0.0414 (19)	0.059 (2)	0.055 (2)	0.0038 (16)	0.0175 (16)	0.0047 (17)
C14	0.0463 (19)	0.0433 (18)	0.0383 (17)	0.0032 (15)	0.0168 (15)	0.0020 (14)
C15	0.0423 (19)	0.054 (2)	0.048 (2)	0.0024 (16)	0.0171 (16)	−0.0055 (17)
C16	0.072 (3)	0.077 (3)	0.047 (2)	0.010 (2)	0.0257 (19)	−0.0065 (19)

Geometric parameters (Å, º) top

O1—C2	1.185 (4)	C7—C8	1.400 (4)
O2—C2	1.359 (4)	C7—H7A	0.9300
O2—C3	1.406 (4)	C8—C9	1.482 (4)
O3—C15	1.353 (4)	C9—C10	1.386 (4)
O3—C14	1.406 (4)	C9—C14	1.393 (4)
O4—C15	1.187 (4)	C10—C11	1.383 (5)
C1—C2	1.487 (5)	C10—H10A	0.9300
C1—H1A	0.9600	C11—C12	1.376 (5)
C1—H1B	0.9600	C11—H11A	0.9300
C1—H1C	0.9600	C12—C13	1.379 (5)
C3—C4	1.377 (5)	C12—H12A	0.9300
C3—C8	1.396 (4)	C13—C14	1.384 (5)
C4—C5	1.385 (6)	C13—H13A	0.9300
C4—H4A	0.9300	C15—C16	1.484 (5)
C5—C6	1.370 (6)	C16—H16A	0.9600
C5—H5A	0.9300	C16—H16B	0.9600
C6—C7	1.387 (5)	C16—H16C	0.9600
C6—H6A	0.9300

C2—O2—C3	118.4 (3)	C7—C8—C9	120.9 (3)
C15—O3—C14	116.4 (3)	C10—C9—C14	117.4 (3)
C2—C1—H1A	109.5	C10—C9—C8	120.0 (3)
C2—C1—H1B	109.5	C14—C9—C8	122.5 (3)
H1A—C1—H1B	109.5	C11—C10—C9	120.8 (3)
C2—C1—H1C	109.5	C11—C10—H10A	119.6
H1A—C1—H1C	109.5	C9—C10—H10A	119.6
H1B—C1—H1C	109.5	C12—C11—C10	120.7 (3)
O1—C2—O2	123.7 (4)	C12—C11—H11A	119.7
O1—C2—C1	126.1 (4)	C10—C11—H11A	119.7
O2—C2—C1	110.2 (3)	C11—C12—C13	119.7 (3)
C4—C3—C8	122.4 (3)	C11—C12—H12A	120.1
C4—C3—O2	120.8 (3)	C13—C12—H12A	120.1
C8—C3—O2	116.6 (3)	C12—C13—C14	119.3 (3)
C3—C4—C5	119.0 (4)	C12—C13—H13A	120.4
C3—C4—H4A	120.5	C14—C13—H13A	120.4
C5—C4—H4A	120.5	C13—C14—C9	122.0 (3)
C6—C5—C4	120.4 (4)	C13—C14—O3	117.8 (3)
C6—C5—H5A	119.8	C9—C14—O3	120.2 (3)
C4—C5—H5A	119.8	O4—C15—O3	122.6 (3)
C5—C6—C7	120.3 (4)	O4—C15—C16	126.0 (4)
C5—C6—H6A	119.8	O3—C15—C16	111.4 (3)
C7—C6—H6A	119.8	C15—C16—H16A	109.5
C6—C7—C8	120.8 (4)	C15—C16—H16B	109.5
C6—C7—H7A	119.6	H16A—C16—H16B	109.5
C8—C7—H7A	119.6	C15—C16—H16C	109.5
C3—C8—C7	117.0 (3)	H16A—C16—H16C	109.5
C3—C8—C9	121.8 (3)	H16B—C16—H16C	109.5

C3—O2—C2—O1	0.7 (5)	C3—C8—C9—C14	−60.2 (4)
C3—O2—C2—C1	−177.8 (3)	C7—C8—C9—C14	126.0 (3)
C2—O2—C3—C4	−63.2 (4)	C14—C9—C10—C11	3.4 (5)
C2—O2—C3—C8	122.9 (3)	C8—C9—C10—C11	−175.8 (3)
C8—C3—C4—C5	−0.5 (5)	C9—C10—C11—C12	−1.8 (5)
O2—C3—C4—C5	−174.1 (3)	C10—C11—C12—C13	−0.2 (6)
C3—C4—C5—C6	0.1 (6)	C11—C12—C13—C14	0.5 (5)
C4—C5—C6—C7	0.4 (6)	C12—C13—C14—C9	1.2 (5)
C5—C6—C7—C8	−0.4 (6)	C12—C13—C14—O3	178.4 (3)
C4—C3—C8—C7	0.6 (5)	C10—C9—C14—C13	−3.1 (5)
O2—C3—C8—C7	174.3 (3)	C8—C9—C14—C13	176.0 (3)
C4—C3—C8—C9	−173.5 (3)	C10—C9—C14—O3	179.8 (3)
O2—C3—C8—C9	0.3 (4)	C8—C9—C14—O3	−1.1 (5)
C6—C7—C8—C3	−0.1 (5)	C15—O3—C14—C13	96.1 (4)
C6—C7—C8—C9	174.0 (3)	C15—O3—C14—C9	−86.7 (4)
C3—C8—C9—C10	118.9 (3)	C14—O3—C15—O4	−0.8 (5)
C7—C8—C9—C10	−54.9 (4)	C14—O3—C15—C16	−179.6 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₄
M_r	270.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	8.8380 (18), 18.204 (4), 8.9620 (18)
β (°)	108.75 (3)
V (Å³)	1365.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.972, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	2643, 2478, 1645
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.156, 1.00
No. of reflections	2478
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.27

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar