Crystal structure of bis­(4-allyl-2-meth­oxy­phen­yl) terephthalate

Kang, S.K.; Han, B.H.

doi:10.1107/S1600536814021229

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 10| October 2014| Page o1138

doi:10.1107/S1600536814021229

Open

access

Crystal structure of bis(4-allyl-2-methoxyphenyl) terephthalate

Sung Kwon Kang ^a ^* and Byung Hee Han ^a

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
^*Correspondence e-mail: skkang@cnu.ac.kr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 23 September 2014; accepted 24 September 2014; online 30 September 2014)

The asymmetric unit of the title compound, C₂₈H₂₆O₆, contains one half-molecule, with the complete molecule generated by a crystallographic inversion center. The central terephthalate and methoxybenzene rings are approximately perpendicular, making a dihedral angle of 80.31 (5)°. No specific directional contacts are noted in the crystal packing. The terminal vinyl group is disordered over two orientations with an occupancy ratio of 0.796 (4):0.204 (4).

Keywords: crystal structure; terephthalate; tyrosinase inhibitors.

CCDC reference: 1025706

1. Related literature

For general background to tyrosinase, see: Ha et al. (2007 ). For the development of tyrosinase inhibitors, see: Battaini et al. (2000 ); Thanigaimalai et al. (2010 ); Cabanes et al. (1994 ). For the structures of related compounds, see: Choi et al. (2011 , 2012 ).

2. Experimental

2.1. Crystal data

C₂₈H₂₆O₆
M_r = 458.49
Triclinic, $[P \overline 1]$
a = 7.8853 (2) Å
b = 9.0404 (3) Å
c = 9.4801 (3) Å
α = 70.660 (4)°
β = 73.817 (3)°
γ = 75.145 (2)°
V = 602.28 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.15 × 0.14 × 0.12 mm

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
21083 measured reflections
3008 independent reflections
1909 reflections with I > 2σ(I)
R_int = 0.050

2.3. Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.173
S = 1.09
3008 reflections
161 parameters
H-atom parameters not refined
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1025706

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814021229/tk5342sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814021229/tk5342Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814021229/tk5342Isup3.cml

checkCIF report

Synthesis and crystallization top

Terephthaloyl chloride and 4-allyl-2-methoxyphenol were purchased from Sigma Chemical Co. Solvents used for organic synthesis were redistilled before used. All other chemicals and solvents were of analytical grade and used without further purification. The title compound was prepared from the reaction of terephthaloyl chloride (0.203 g, 1 mmol) and 4-allyl-2-methoxyphenol (0.378 g, 2.3 mmol) in triethylamine (8 ml) as a solvent. After stirring for 8 h at 333 K under nitrogen, the reaction mixture was quenched with water and extracted with ethyl acetate. After drying over anhydrous calcium chloride, the solvent was removed by rotary evaporation. The crude product was purified by column chromatography on silica gel using dichloromethane: ethylacetate (2:1,v/v) as an eluent. The solution was evaporated to give the product of 0.32 g (70%). Crystals were obtained by slow evaporation from its solution in ethyl alcohol at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93-0.97 Å, and with U_iso(H) = 1.5U_eq(C) for methyl, and 1.2U_eq(C) for all other H atoms. The vinyl group is disordered over two positions with an occupancy ratio of 0.796 (4):0.204 (4).

Related literature top

For general background to tyrosinase, see: Ha et al. (2007). For the development of tyrosinase inhibitors, see: Battaini et al. (2000); Thanigaimalai et al. (2010); Cabanes et al. (1994). For the structures of related compounds, see: Choi et al. (2011, 2012).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. Only major components of the disordered vinyl group are shown. Unlabeled atoms are related by -x, -y, 1-z]

Crystal structure of bis(4-allyl-2-methoxyphenyl) terephthalate top

Crystal data top

C₂₈H₂₆O₆	Z = 1
M_r = 458.49	F(000) = 242
Triclinic, P1	D_x = 1.264 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8853 (2) Å	Cell parameters from 5115 reflections
b = 9.0404 (3) Å	θ = 2.3–26.7°
c = 9.4801 (3) Å	µ = 0.09 mm⁻¹
α = 70.660 (4)°	T = 296 K
β = 73.817 (3)°	Block, colourless
γ = 75.145 (2)°	0.15 × 0.14 × 0.12 mm
V = 602.28 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	R_int = 0.050
Radiation source: fine-focus sealed tube	θ_max = 28.4°, θ_min = 2.3°
ϕ and ω scans	h = −10→10
21083 measured reflections	k = −12→12
3008 independent reflections	l = −12→12
1909 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters not refined
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.0939P)² + 0.0172P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3008 reflections	Δρ_max = 0.28 e Å⁻³
161 parameters	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₈H₂₆O₆	γ = 75.145 (2)°
M_r = 458.49	V = 602.28 (4) Å³
Triclinic, P1	Z = 1
a = 7.8853 (2) Å	Mo Kα radiation
b = 9.0404 (3) Å	µ = 0.09 mm⁻¹
c = 9.4801 (3) Å	T = 296 K
α = 70.660 (4)°	0.15 × 0.14 × 0.12 mm
β = 73.817 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1909 reflections with I > 2σ(I)
21083 measured reflections	R_int = 0.050
3008 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.173	H-atom parameters not refined
S = 1.09	Δρ_max = 0.28 e Å⁻³
3008 reflections	Δρ_min = −0.28 e Å⁻³
161 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.13052 (18)	0.06171 (17)	0.37786 (16)	0.0472 (4)
C2	0.17983 (19)	−0.04861 (19)	0.50781 (18)	0.0573 (4)
H2	0.3002	−0.0812	0.5133	0.069*
C3	−0.04832 (19)	0.10990 (19)	0.37058 (17)	0.0571 (4)
H3	−0.0808	0.1842	0.2832	0.068*
C4	0.26416 (18)	0.13439 (17)	0.24324 (17)	0.0495 (4)
O5	0.22778 (14)	0.22924 (14)	0.12885 (12)	0.0638 (3)
O6	0.43403 (13)	0.08074 (13)	0.26489 (12)	0.0605 (3)
C7	0.56778 (19)	0.15655 (18)	0.15091 (17)	0.0528 (4)
C8	0.58804 (18)	0.30400 (19)	0.15298 (16)	0.0510 (4)
C9	0.72527 (19)	0.37414 (19)	0.04596 (17)	0.0533 (4)
H9	0.74	0.4734	0.0448	0.064*
C10	0.8414 (2)	0.2986 (2)	−0.05965 (17)	0.0563 (4)
C11	0.8181 (2)	0.1522 (2)	−0.0585 (2)	0.0629 (4)
H11	0.8951	0.1007	−0.1287	0.075*
C12	0.6796 (2)	0.0814 (2)	0.04764 (19)	0.0606 (4)
H12	0.6634	−0.0171	0.048	0.073*
O13	0.47003 (14)	0.36676 (15)	0.26266 (13)	0.0671 (4)
C14	0.5024 (3)	0.5069 (3)	0.2795 (2)	0.0772 (5)
H14A	0.4104	0.5401	0.3594	0.116*
H14B	0.5013	0.5901	0.1852	0.116*
H14C	0.6174	0.4852	0.3054	0.116*
C15	0.9940 (3)	0.3774 (3)	−0.1702 (2)	0.0793 (6)
H15A	0.9572	0.4919	−0.1881	0.095*
H15B	1.0958	0.345	−0.1214	0.095*
C16	1.0537 (4)	0.3429 (5)	−0.3182 (3)	0.1076 (12)	0.796 (4)
H16	0.9698	0.3704	−0.379	0.129*	0.796 (4)
C17	1.2197 (6)	0.2748 (5)	−0.3724 (4)	0.0998 (13)	0.796 (4)
H17A	1.3071	0.2457	−0.3147	0.12*	0.796 (4)
H17B	1.2481	0.2565	−0.4679	0.12*	0.796 (4)
C16A	1.1284 (19)	0.308 (2)	−0.2471 (13)	0.1076 (12)	0.204 (4)
H16A	1.2244	0.2457	−0.2032	0.129*	0.204 (4)
C17A	1.131 (2)	0.328 (2)	−0.4139 (18)	0.0998 (13)	0.204 (4)
H17C	1.0342	0.3905	−0.4567	0.12*	0.204 (4)
H17D	1.2291	0.2776	−0.4728	0.12*	0.204 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (7)	0.0501 (8)	0.0454 (7)	−0.0193 (6)	−0.0051 (6)	−0.0048 (6)
C2	0.0388 (7)	0.0652 (9)	0.0570 (9)	−0.0165 (7)	−0.0099 (6)	0.0022 (7)
C3	0.0470 (8)	0.0636 (9)	0.0493 (8)	−0.0173 (7)	−0.0112 (6)	0.0050 (7)
C4	0.0437 (7)	0.0533 (8)	0.0483 (8)	−0.0176 (6)	−0.0061 (6)	−0.0064 (6)
O5	0.0527 (6)	0.0754 (7)	0.0511 (6)	−0.0245 (5)	−0.0099 (5)	0.0068 (5)
O6	0.0411 (5)	0.0664 (7)	0.0572 (6)	−0.0207 (5)	−0.0047 (5)	0.0078 (5)
C7	0.0397 (7)	0.0609 (9)	0.0469 (8)	−0.0186 (6)	−0.0056 (6)	0.0033 (7)
C8	0.0408 (7)	0.0666 (9)	0.0430 (7)	−0.0167 (6)	−0.0059 (6)	−0.0093 (7)
C9	0.0468 (8)	0.0635 (9)	0.0487 (8)	−0.0217 (7)	−0.0058 (6)	−0.0091 (7)
C10	0.0442 (8)	0.0669 (10)	0.0509 (8)	−0.0198 (7)	−0.0012 (6)	−0.0078 (7)
C11	0.0493 (8)	0.0692 (10)	0.0624 (10)	−0.0157 (7)	0.0028 (7)	−0.0169 (8)
C12	0.0504 (8)	0.0576 (9)	0.0676 (10)	−0.0171 (7)	−0.0050 (7)	−0.0102 (8)
O13	0.0565 (7)	0.0899 (9)	0.0554 (7)	−0.0283 (6)	0.0073 (5)	−0.0253 (6)
C14	0.0706 (12)	0.1002 (14)	0.0715 (12)	−0.0233 (10)	−0.0042 (9)	−0.0409 (11)
C15	0.0622 (11)	0.0902 (13)	0.0771 (12)	−0.0381 (9)	0.0212 (9)	−0.0240 (10)
C16	0.104 (2)	0.185 (3)	0.0448 (15)	−0.100 (2)	0.0031 (13)	−0.0068 (17)
C17	0.112 (3)	0.115 (3)	0.074 (2)	−0.060 (2)	0.0317 (19)	−0.041 (2)
C16A	0.104 (2)	0.185 (3)	0.0448 (15)	−0.100 (2)	0.0031 (13)	−0.0068 (17)
C17A	0.112 (3)	0.115 (3)	0.074 (2)	−0.060 (2)	0.0317 (19)	−0.041 (2)

Geometric parameters (Å, º) top

C1—C3	1.379 (2)	C11—H11	0.93
C1—C2	1.385 (2)	C12—H12	0.93
C1—C4	1.4903 (18)	O13—C14	1.421 (2)
C2—C3ⁱ	1.3844 (19)	C14—H14A	0.96
C2—H2	0.93	C14—H14B	0.96
C3—C2ⁱ	1.3844 (19)	C14—H14C	0.96
C3—H3	0.93	C15—C16A	1.257 (15)
C4—O5	1.1937 (17)	C15—C16	1.461 (4)
C4—O6	1.3512 (17)	C15—H15A	0.97
O6—C7	1.4123 (15)	C15—H15B	0.97
C7—C12	1.360 (2)	C16—C17	1.333 (5)
C7—C8	1.390 (2)	C16—H16	0.93
C8—O13	1.3600 (18)	C17—H17A	0.93
C8—C9	1.3843 (18)	C17—H17B	0.93
C9—C10	1.388 (2)	C16A—C17A	1.53 (2)
C9—H9	0.93	C16A—H16A	0.93
C10—C11	1.378 (2)	C17A—H17C	0.93
C10—C15	1.5154 (19)	C17A—H17D	0.93
C11—C12	1.391 (2)

C3—C1—C2	119.99 (12)	C7—C12—H12	120.1
C3—C1—C4	117.51 (13)	C11—C12—H12	120.1
C2—C1—C4	122.49 (13)	C8—O13—C14	117.13 (12)
C3ⁱ—C2—C1	119.41 (14)	O13—C14—H14A	109.5
C3ⁱ—C2—H2	120.3	O13—C14—H14B	109.5
C1—C2—H2	120.3	H14A—C14—H14B	109.5
C1—C3—C2ⁱ	120.59 (14)	O13—C14—H14C	109.5
C1—C3—H3	119.7	H14A—C14—H14C	109.5
C2ⁱ—C3—H3	119.7	H14B—C14—H14C	109.5
O5—C4—O6	123.12 (12)	C16A—C15—C10	124.7 (6)
O5—C4—C1	124.73 (13)	C16—C15—C10	116.08 (18)
O6—C4—C1	112.14 (12)	C16—C15—H15A	108.3
C4—O6—C7	116.11 (11)	C10—C15—H15A	108.3
C12—C7—C8	121.45 (13)	C16—C15—H15B	108.3
C12—C7—O6	120.02 (14)	C10—C15—H15B	108.3
C8—C7—O6	118.43 (14)	H15A—C15—H15B	107.4
O13—C8—C9	125.43 (14)	C17—C16—C15	124.7 (4)
O13—C8—C7	116.30 (12)	C17—C16—H16	117.6
C9—C8—C7	118.27 (14)	C15—C16—H16	117.6
C8—C9—C10	121.04 (15)	C16—C17—H17A	120
C8—C9—H9	119.5	C16—C17—H17B	120
C10—C9—H9	119.5	H17A—C17—H17B	120
C11—C10—C9	119.29 (14)	C15—C16A—C17A	118.7 (15)
C11—C10—C15	121.73 (15)	C15—C16A—H16A	120.7
C9—C10—C15	118.95 (15)	C17A—C16A—H16A	120.7
C10—C11—C12	120.13 (16)	C16A—C17A—H17C	120
C10—C11—H11	119.9	C16A—C17A—H17D	120
C12—C11—H11	119.9	H17C—C17A—H17D	120
C7—C12—C11	119.82 (16)

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₆O₆
M_r	458.49
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.8853 (2), 9.0404 (3), 9.4801 (3)
α, β, γ (°)	70.660 (4), 73.817 (3), 75.145 (2)
V (Å³)	602.28 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21083, 3008, 1909
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.173, 1.09
No. of reflections	3008
No. of parameters	161
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.28

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS2013 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Acknowledgements

This work was supported by a research fund from Chungnam National University.

References

Battaini, G., Monzani, E., Casella, L., Santagostini, L. & Pagliarin, R. (2000). J. Biol. Inorg. Chem. 5, 262–268. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cabanes, J., Chazarra, S. & Garcia-Carmona, F. (1994). J. Pharm. Pharmacol. 46, 982–985. CrossRef CAS PubMed Google Scholar
Choi, H., Shim, Y. S., Han, B. H., Kang, S. K. & Sung, C. K. (2011). Acta Cryst. E67, o2865. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H., Shim, Y. S., Han, B. H., Kang, S. K. & Sung, C. K. (2012). Acta Cryst. E68, o966. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ha, Y. M., Chung, S. W., Song, S. H., Lee, H. J., Suh, H. & Chung, H. Y. (2007). Biol. Pharm. Bull. 30, 1711–1715. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thanigaimalai, P., Hoang, T. A., Lee, K. C., Bang, S. C., Sharma, V. K., Yun, C. Y., Roh, E., Hwang, B. Y., Kim, Y. & Jung, S. H. (2010). Bioorg. Med. Chem. Lett. 20, 2991–2993. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 10| October 2014| Page o1138

doi:10.1107/S1600536814021229

Open

access