Dimethyl 1,8-bis­(4-methyl­phen­yl)-11-oxatri­cyclo­[6.2.1.02,7]undeca-2,4,6,9-tetra­ene-9,10-di­carboxyl­ate

Balakrishnan, B.; Nandakumar, M.; Seshadri, P.R.; Mohanakrishnan, A.K.

doi:10.1107/S1600536813013305

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o951

doi:10.1107/S1600536813013305

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Dimethyl 1,8-bis(4-methylphenyl)-11-oxatricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylate

B. Balakrishnan,^a Meganathan Nandakumar,^b P. R. Seshadri ^c ^* and Arasambattu K. Mohanakrishnan ^b

^aDepartment of Physics, P.T. Lee Chengalvaraya Naicker College of Engineering and Technology, Kancheepuram 631 502, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cPostgraduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 1 May 2013; accepted 14 May 2013; online 25 May 2013)

The title compound, C₂₈H₂₄O₅, consists of a fused tricyclic system containing two five-membered rings and one six-membered ring. The five-membered rings both exhibit an envelope conformation with the O atom at the flap, whereas the six-membered ring adopts a boat conformation. The dihedral angle between the 4-methylphenyl rings at the 1,8-positions is 76.4 (1)°. In the crystal, molecules are stacked in columns along the a axis through C—H⋯O interactions.

Related literature

For background to Diels–Alder reactions, see: Denmark & Thorarensen (1996 ). For related structures, see: Bailey et al. (1995 ); Balakrishnan et al. (2013 ); Takahashi et al. (2003 ). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₈H₂₄O₅
M_r = 440.47
Monoclinic, P 2₁ /c
a = 8.9018 (4) Å
b = 25.6357 (8) Å
c = 11.0961 (4) Å
β = 113.369 (1)°
V = 2324.46 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.975, T_max = 0.983
29434 measured reflections
6904 independent reflections
4338 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.170
S = 1.03
6904 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13C⋯O3ⁱ	0.96	2.56	3.461 (3)	157
C28—H28B⋯O3ⁱⁱ	0.96	2.52	3.478 (3)	173
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013305/is5270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013305/is5270Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013305/is5270Isup3.cml

checkCIF report

Comment top

The Diels-Alder reaction is among the most powerful C—C bond forming process and one of the most widely used and studied transformation in organic chemistry. The isobenzofuran have found extensive use as reactive diene in intra and inter molecular Diels-Alder reactions for the rapid construction of poly cyclic ring (Denmark & Thorarensen, 1996).

The title compound, C₂₈H₂₄O₅, comprises a fused tricyclic system and two 4-methylphenyl rings attached to this system (Fig. 1). The tricyclic system consists of two 5-membered rings and one aromatic ring. In addition, two carboxylate units are attached to the tricyclic system. Geometrical parameters agree well with reported structures (Bailey et al., 1995; Takahashi et al., 2003; Balakrishnan et al., 2013). The 5-membered ring C1/C2/C7/C8/O1 adopts an envelope conformation with atom O1 displaced by -0.772 Å from the mean plane of the other ring atoms C1/C2/C7/C8. The puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983) are q₂ = 0.530 (1) Å, ϕ = 143.5 (2)°, Δ_S(O1) = 0.004 (1)° and Δ₂(O1) = 0.319 (1)°. The second 5-membered ring C1/C23/C26/C8/O1 also adopts an envelope conformation with atom O1 displaced by -0.776 Å from the mean plane of the other ring atoms C1/C23/C26/C8. The puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983) are q₂ = 0.556 (1) Å, ϕ = -33.2 (2)°, Δ_S(O1) = 0.022 (1)° and Δ₂(O1) = 0.323 (1)°. The six membered ring C1/C2/C7/C8/C26/C23 adopts a boat conformation with puckering parameter q₂ = 0.999 (1) Å, θ = 90.4 (1)° and ϕ = 1.1 (1)°.

The dihedral angle between the mean planes of the rings C1/C2/C7/C8/O1 and C1/C23/C26/C8/O1 is 72.5 (1)°. The mean plane of the tricyclic system makes dihedral angles of 31.4 (1) and 69.9 (1)°, respectively, with the 4-methylphenyl rings. The dihedral angle between the terminal 4-methylphenyl rings is 76.4 (1). The carboxylate ligand at the C26 carbon atom lies practically in the plane of the C26/C8/O1/C1 five ring [C23—C26—C27—O5 torsion angle = -7.1 (2)°], while that at the C23 carbon atom is turned out of this plane [C26—C23—C24—O3 torsion angle = 72.0 (2)°]. Centrosymmetric dimers are formed by C—H···O hydrogen bond.

Related literature top

For background to Diels–Alder reactions, see: Denmark & Thorarensen (1996). For related structures, see: Bailey et al. (1995); Balakrishnan et al. (2013); Takahashi et al. (2003). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

Diels-Alder reaction of 1,3-di-p-tolylbenzo[c]furan (1.0 g, 3.36 mmol) in dry DCM was added DMAD (0.53 g, 3.69 mmol) and the reaction mixture was stirred for 0.5 h at room temperature under nitrogen atmosphere. The solvent was removed and solid was washed with methanol to give compound as colourless solid. Yield: 1.07 g (80%). M.P.: 116 °C. This adduct was crystallized from CHCl₃/CH₃OH (3:1) by the slow evaporation method.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

Dimethyl 1,8-bis(4-methylphenyl)-11-oxatricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylate top

Crystal data top

C₂₈H₂₄O₅	Z = 4
M_r = 440.47	F(000) = 928
Monoclinic, P2₁/c	D_x = 1.259 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9018 (4) Å	θ = 2.2–30.2°
b = 25.6357 (8) Å	µ = 0.09 mm⁻¹
c = 11.0961 (4) Å	T = 293 K
β = 113.369 (1)°	Black, colourless
V = 2324.46 (15) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	6904 independent reflections
Radiation source: fine-focus sealed tube	4338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scan	θ_max = 30.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.975, T_max = 0.983	k = −36→34
29434 measured reflections	l = −15→15

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.0787P)² + 0.4566P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6904 reflections	Δρ_max = 0.30 e Å⁻³
299 parameters	Δρ_min = −0.17 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: 0.0071 (14)

Crystal data top

C₂₈H₂₄O₅	V = 2324.46 (15) Å³
M_r = 440.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9018 (4) Å	µ = 0.09 mm⁻¹
b = 25.6357 (8) Å	T = 293 K
c = 11.0961 (4) Å	0.30 × 0.20 × 0.20 mm
β = 113.369 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6904 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4338 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.034
29434 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
6904 reflections	Δρ_min = −0.17 e Å⁻³
299 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
C8	0.77122 (19)	0.06795 (6)	0.26149 (15)	0.0371 (3)
C7	0.8610 (2)	0.10788 (6)	0.36867 (16)	0.0398 (3)
C6	0.9676 (2)	0.10415 (7)	0.49831 (16)	0.0465 (4)
H6	0.9919	0.0721	0.5411	0.056*
C5	1.0378 (2)	0.15018 (8)	0.56286 (18)	0.0537 (5)
H5	1.1099	0.1488	0.6506	0.064*
C4	1.0032 (2)	0.19756 (8)	0.5002 (2)	0.0549 (5)
H4	1.0505	0.2277	0.5465	0.066*
C3	0.8982 (2)	0.20119 (7)	0.36820 (18)	0.0479 (4)
H3	0.8759	0.2332	0.3252	0.057*
C2	0.82902 (19)	0.15609 (6)	0.30388 (16)	0.0391 (3)
C1	0.71914 (19)	0.14347 (6)	0.15944 (15)	0.0380 (3)
C16	0.60917 (19)	0.18477 (6)	0.07505 (16)	0.0409 (4)
C22	0.6743 (2)	0.22872 (7)	0.0416 (2)	0.0570 (5)
H22	0.7873	0.2329	0.0737	0.068*
C21	0.5732 (3)	0.26660 (8)	−0.0392 (2)	0.0621 (5)
H21	0.6193	0.2957	−0.0613	0.075*
C19	0.4047 (2)	0.26197 (8)	−0.08750 (18)	0.0559 (5)
C20	0.2962 (3)	0.30280 (11)	−0.1783 (2)	0.0864 (8)
H20A	0.1836	0.2934	−0.2025	0.130*
H20C	0.3191	0.3051	−0.2557	0.130*
H20B	0.3169	0.3360	−0.1345	0.130*
C18	0.3410 (2)	0.21909 (8)	−0.0500 (2)	0.0580 (5)
H18	0.2281	0.2158	−0.0792	0.070*
C17	0.4401 (2)	0.18069 (7)	0.03012 (18)	0.0499 (4)
H17	0.3935	0.1521	0.0539	0.060*
C9	0.7112 (2)	0.01647 (6)	0.28848 (16)	0.0420 (4)
C10	0.6997 (2)	0.00459 (8)	0.40519 (19)	0.0574 (5)
H10	0.7347	0.0286	0.4735	0.069*
C11	0.6362 (3)	−0.04307 (10)	0.4220 (2)	0.0726 (6)
H11	0.6310	−0.0506	0.5022	0.087*
C12	0.5807 (2)	−0.07938 (8)	0.3224 (2)	0.0665 (6)
C13	0.5158 (3)	−0.13196 (10)	0.3413 (3)	0.1046 (11)
H13A	0.5200	−0.1343	0.4289	0.157*
H13B	0.5816	−0.1591	0.3276	0.157*
H13C	0.4046	−0.1358	0.2794	0.157*
C14	0.5881 (3)	−0.06670 (8)	0.2050 (2)	0.0650 (5)
H14	0.5488	−0.0902	0.1356	0.078*
C15	0.6529 (2)	−0.01967 (7)	0.1876 (2)	0.0554 (5)
H15	0.6574	−0.0122	0.1071	0.066*
C26	0.87077 (18)	0.06868 (6)	0.17415 (14)	0.0363 (3)
C27	1.0114 (2)	0.03366 (6)	0.19642 (16)	0.0407 (4)
C28	1.2486 (2)	0.02100 (9)	0.1527 (2)	0.0694 (6)
H28A	1.2993	0.0355	0.0984	0.104*
H28B	1.2249	−0.0152	0.1315	0.104*
H28C	1.3214	0.0243	0.2434	0.104*
C23	0.83616 (18)	0.11356 (6)	0.10885 (14)	0.0359 (3)
C24	0.91045 (19)	0.13555 (6)	0.02149 (15)	0.0380 (3)
C25	0.9345 (4)	0.12516 (10)	−0.1798 (2)	0.0781 (7)
H25A	0.8917	0.1039	−0.2573	0.117*
H25B	1.0511	0.1209	−0.1384	0.117*
H25C	0.9091	0.1611	−0.2033	0.117*
O1	0.63095 (13)	0.09913 (4)	0.17856 (11)	0.0401 (3)
O4	1.0475 (2)	−0.00215 (6)	0.27114 (16)	0.0750 (5)
O5	1.09867 (17)	0.04857 (6)	0.13005 (15)	0.0648 (4)
O2	0.99992 (17)	0.17240 (5)	0.04755 (13)	0.0595 (4)
O3	0.86178 (17)	0.10946 (5)	−0.08975 (12)	0.0566 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0394 (8)	0.0369 (8)	0.0392 (8)	0.0058 (6)	0.0199 (7)	0.0033 (6)
C7	0.0438 (8)	0.0403 (8)	0.0424 (8)	0.0035 (7)	0.0246 (7)	−0.0017 (6)
C6	0.0512 (10)	0.0517 (10)	0.0426 (9)	0.0039 (8)	0.0250 (8)	0.0009 (7)
C5	0.0534 (10)	0.0666 (12)	0.0443 (9)	−0.0025 (9)	0.0227 (8)	−0.0100 (9)
C4	0.0575 (11)	0.0533 (11)	0.0607 (11)	−0.0079 (9)	0.0307 (9)	−0.0196 (9)
C3	0.0523 (10)	0.0391 (8)	0.0613 (11)	0.0028 (7)	0.0321 (9)	−0.0042 (8)
C2	0.0403 (8)	0.0382 (8)	0.0464 (8)	0.0055 (6)	0.0252 (7)	−0.0011 (6)
C1	0.0376 (8)	0.0360 (8)	0.0465 (8)	0.0027 (6)	0.0230 (7)	0.0026 (6)
C16	0.0398 (8)	0.0394 (8)	0.0484 (9)	0.0075 (6)	0.0228 (7)	0.0041 (7)
C22	0.0434 (9)	0.0532 (11)	0.0804 (13)	0.0116 (8)	0.0308 (9)	0.0201 (10)
C21	0.0627 (12)	0.0557 (11)	0.0822 (14)	0.0194 (9)	0.0438 (11)	0.0275 (10)
C19	0.0558 (11)	0.0655 (12)	0.0493 (10)	0.0225 (9)	0.0239 (9)	0.0141 (9)
C20	0.0793 (16)	0.1036 (19)	0.0741 (15)	0.0402 (15)	0.0280 (13)	0.0407 (14)
C18	0.0397 (9)	0.0655 (12)	0.0632 (12)	0.0108 (9)	0.0146 (9)	0.0046 (10)
C17	0.0450 (9)	0.0467 (9)	0.0602 (11)	0.0031 (7)	0.0230 (8)	0.0026 (8)
C9	0.0424 (8)	0.0381 (8)	0.0486 (9)	0.0040 (7)	0.0214 (7)	0.0058 (7)
C10	0.0621 (12)	0.0612 (11)	0.0511 (10)	−0.0081 (9)	0.0248 (9)	0.0072 (9)
C11	0.0665 (13)	0.0842 (16)	0.0634 (13)	−0.0132 (12)	0.0219 (11)	0.0292 (12)
C12	0.0456 (10)	0.0532 (11)	0.0907 (16)	−0.0019 (9)	0.0164 (10)	0.0258 (11)
C13	0.0777 (17)	0.0762 (16)	0.138 (3)	−0.0227 (14)	0.0192 (17)	0.0424 (17)
C14	0.0620 (12)	0.0479 (10)	0.0832 (15)	−0.0097 (9)	0.0268 (11)	−0.0047 (10)
C15	0.0648 (12)	0.0475 (10)	0.0594 (11)	−0.0070 (9)	0.0306 (10)	−0.0042 (8)
C26	0.0387 (8)	0.0355 (7)	0.0377 (7)	0.0030 (6)	0.0183 (6)	−0.0014 (6)
C27	0.0432 (9)	0.0404 (8)	0.0387 (8)	0.0068 (7)	0.0165 (7)	−0.0037 (7)
C28	0.0493 (11)	0.0777 (14)	0.0899 (16)	0.0173 (10)	0.0368 (11)	−0.0038 (12)
C23	0.0345 (7)	0.0376 (8)	0.0376 (8)	0.0012 (6)	0.0163 (6)	−0.0017 (6)
C24	0.0364 (8)	0.0394 (8)	0.0402 (8)	0.0020 (6)	0.0171 (6)	0.0003 (6)
C25	0.1121 (19)	0.0845 (15)	0.0655 (13)	−0.0214 (14)	0.0648 (14)	−0.0108 (12)
O1	0.0375 (6)	0.0379 (6)	0.0494 (6)	0.0030 (4)	0.0218 (5)	0.0054 (5)
O4	0.0805 (10)	0.0741 (9)	0.0850 (10)	0.0389 (8)	0.0484 (9)	0.0360 (8)
O5	0.0582 (8)	0.0647 (8)	0.0903 (10)	0.0230 (7)	0.0495 (8)	0.0212 (7)
O2	0.0621 (8)	0.0579 (8)	0.0655 (8)	−0.0220 (7)	0.0329 (7)	−0.0116 (6)
O3	0.0732 (9)	0.0604 (8)	0.0466 (7)	−0.0216 (7)	0.0349 (6)	−0.0126 (6)

Geometric parameters (Å, º) top

C8—O1	1.4607 (18)	C17—H17	0.9300
C8—C9	1.498 (2)	C9—C10	1.373 (2)
C8—C7	1.532 (2)	C9—C15	1.386 (3)
C8—C26	1.551 (2)	C10—C11	1.390 (3)
C7—C6	1.377 (2)	C10—H10	0.9300
C7—C2	1.401 (2)	C11—C12	1.378 (3)
C6—C5	1.393 (3)	C11—H11	0.9300
C6—H6	0.9300	C12—C14	1.369 (3)
C5—C4	1.372 (3)	C12—C13	1.514 (3)
C5—H5	0.9300	C13—H13A	0.9600
C4—C3	1.393 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C3—C2	1.370 (2)	C14—C15	1.383 (3)
C3—H3	0.9300	C14—H14	0.9300
C2—C1	1.545 (2)	C15—H15	0.9300
C1—O1	1.4441 (18)	C26—C23	1.329 (2)
C1—C16	1.493 (2)	C26—C27	1.480 (2)
C1—C23	1.566 (2)	C27—O4	1.192 (2)
C16—C22	1.384 (2)	C27—O5	1.321 (2)
C16—C17	1.389 (2)	C28—O5	1.441 (2)
C22—C21	1.384 (3)	C28—H28A	0.9600
C22—H22	0.9300	C28—H28B	0.9600
C21—C19	1.383 (3)	C28—H28C	0.9600
C21—H21	0.9300	C23—C24	1.484 (2)
C19—C18	1.375 (3)	C24—O2	1.1948 (19)
C19—C20	1.507 (3)	C24—O3	1.3170 (19)
C20—H20A	0.9600	C25—O3	1.447 (2)
C20—H20C	0.9600	C25—H25A	0.9600
C20—H20B	0.9600	C25—H25B	0.9600
C18—C17	1.384 (3)	C25—H25C	0.9600
C18—H18	0.9300

O1—C8—C9	108.93 (12)	C16—C17—H17	120.0
O1—C8—C7	100.11 (11)	C10—C9—C15	118.01 (16)
C9—C8—C7	123.44 (13)	C10—C9—C8	123.36 (16)
O1—C8—C26	99.05 (11)	C15—C9—C8	118.46 (15)
C9—C8—C26	118.25 (12)	C9—C10—C11	120.5 (2)
C7—C8—C26	103.04 (12)	C9—C10—H10	119.7
C6—C7—C2	120.85 (15)	C11—C10—H10	119.7
C6—C7—C8	134.08 (15)	C12—C11—C10	121.4 (2)
C2—C7—C8	104.71 (13)	C12—C11—H11	119.3
C7—C6—C5	117.45 (17)	C10—C11—H11	119.3
C7—C6—H6	121.3	C14—C12—C11	117.75 (18)
C5—C6—H6	121.3	C14—C12—C13	120.6 (2)
C4—C5—C6	121.63 (18)	C11—C12—C13	121.7 (2)
C4—C5—H5	119.2	C12—C13—H13A	109.5
C6—C5—H5	119.2	C12—C13—H13B	109.5
C5—C4—C3	120.92 (17)	H13A—C13—H13B	109.5
C5—C4—H4	119.5	C12—C13—H13C	109.5
C3—C4—H4	119.5	H13A—C13—H13C	109.5
C2—C3—C4	117.82 (17)	H13B—C13—H13C	109.5
C2—C3—H3	121.1	C12—C14—C15	121.3 (2)
C4—C3—H3	121.1	C12—C14—H14	119.3
C3—C2—C7	121.29 (16)	C15—C14—H14	119.3
C3—C2—C1	133.32 (15)	C14—C15—C9	120.90 (19)
C7—C2—C1	105.29 (13)	C14—C15—H15	119.6
O1—C1—C16	113.01 (12)	C9—C15—H15	119.6
O1—C1—C2	99.77 (12)	C23—C26—C27	127.89 (14)
C16—C1—C2	119.34 (13)	C23—C26—C8	106.55 (12)
O1—C1—C23	98.34 (11)	C27—C26—C8	122.93 (13)
C16—C1—C23	119.10 (13)	O4—C27—O5	123.69 (15)
C2—C1—C23	103.71 (12)	O4—C27—C26	124.04 (16)
C22—C16—C17	118.35 (16)	O5—C27—C26	112.14 (14)
C22—C16—C1	120.35 (15)	O5—C28—H28A	109.5
C17—C16—C1	121.29 (15)	O5—C28—H28B	109.5
C16—C22—C21	120.69 (18)	H28A—C28—H28B	109.5
C16—C22—H22	119.7	O5—C28—H28C	109.5
C21—C22—H22	119.7	H28A—C28—H28C	109.5
C19—C21—C22	121.19 (18)	H28B—C28—H28C	109.5
C19—C21—H21	119.4	C26—C23—C24	128.15 (14)
C22—C21—H21	119.4	C26—C23—C1	105.77 (12)
C18—C19—C21	117.71 (17)	C24—C23—C1	125.47 (13)
C18—C19—C20	121.7 (2)	O2—C24—O3	124.63 (15)
C21—C19—C20	120.6 (2)	O2—C24—C23	124.68 (14)
C19—C20—H20A	109.5	O3—C24—C23	110.67 (13)
C19—C20—H20C	109.5	O3—C25—H25A	109.5
H20A—C20—H20C	109.5	O3—C25—H25B	109.5
C19—C20—H20B	109.5	H25A—C25—H25B	109.5
H20A—C20—H20B	109.5	O3—C25—H25C	109.5
H20C—C20—H20B	109.5	H25A—C25—H25C	109.5
C19—C18—C17	121.92 (18)	H25B—C25—H25C	109.5
C19—C18—H18	119.0	C1—O1—C8	98.32 (11)
C17—C18—H18	119.0	C27—O5—C28	117.97 (15)
C18—C17—C16	120.06 (17)	C24—O3—C25	115.78 (15)
C18—C17—H17	120.0

O1—C8—C7—C6	154.22 (17)	C15—C9—C10—C11	2.0 (3)
C9—C8—C7—C6	33.4 (3)	C8—C9—C10—C11	177.15 (18)
C26—C8—C7—C6	−103.93 (19)	C9—C10—C11—C12	−1.0 (3)
O1—C8—C7—C2	−32.90 (14)	C10—C11—C12—C14	−0.9 (3)
C9—C8—C7—C2	−153.74 (14)	C10—C11—C12—C13	178.2 (2)
C26—C8—C7—C2	68.95 (14)	C11—C12—C14—C15	1.7 (3)
C2—C7—C6—C5	2.0 (2)	C13—C12—C14—C15	−177.4 (2)
C8—C7—C6—C5	173.92 (16)	C12—C14—C15—C9	−0.6 (3)
C7—C6—C5—C4	−0.3 (3)	C10—C9—C15—C14	−1.3 (3)
C6—C5—C4—C3	−1.2 (3)	C8—C9—C15—C14	−176.61 (17)
C5—C4—C3—C2	1.0 (3)	O1—C8—C26—C23	30.30 (15)
C4—C3—C2—C7	0.7 (2)	C9—C8—C26—C23	147.58 (14)
C4—C3—C2—C1	−175.06 (16)	C7—C8—C26—C23	−72.38 (15)
C6—C7—C2—C3	−2.2 (2)	O1—C8—C26—C27	−166.84 (13)
C8—C7—C2—C3	−176.24 (14)	C9—C8—C26—C27	−49.6 (2)
C6—C7—C2—C1	174.58 (14)	C7—C8—C26—C27	90.48 (16)
C8—C7—C2—C1	0.54 (15)	C23—C26—C27—O4	168.97 (18)
C3—C2—C1—O1	−151.42 (17)	C8—C26—C27—O4	9.9 (3)
C7—C2—C1—O1	32.37 (14)	C23—C26—C27—O5	−7.1 (2)
C3—C2—C1—C16	−27.9 (2)	C8—C26—C27—O5	−166.12 (14)
C7—C2—C1—C16	155.86 (13)	C27—C26—C23—C24	12.2 (3)
C3—C2—C1—C23	107.43 (19)	C8—C26—C23—C24	173.96 (14)
C7—C2—C1—C23	−68.79 (14)	C27—C26—C23—C1	−159.09 (15)
O1—C1—C16—C22	−176.73 (15)	C8—C26—C23—C1	2.64 (16)
C2—C1—C16—C22	66.5 (2)	O1—C1—C23—C26	−35.12 (15)
C23—C1—C16—C22	−62.1 (2)	C16—C1—C23—C26	−157.38 (14)
O1—C1—C16—C17	4.4 (2)	C2—C1—C23—C26	67.14 (15)
C2—C1—C16—C17	−112.39 (18)	O1—C1—C23—C24	153.27 (14)
C23—C1—C16—C17	119.00 (17)	C16—C1—C23—C24	31.0 (2)
C17—C16—C22—C21	−2.6 (3)	C2—C1—C23—C24	−104.47 (16)
C1—C16—C22—C21	178.46 (18)	C26—C23—C24—O2	−109.2 (2)
C16—C22—C21—C19	0.7 (3)	C1—C23—C24—O2	60.5 (2)
C22—C21—C19—C18	1.6 (3)	C26—C23—C24—O3	72.0 (2)
C22—C21—C19—C20	−178.3 (2)	C1—C23—C24—O3	−118.32 (16)
C21—C19—C18—C17	−1.9 (3)	C16—C1—O1—C8	179.75 (12)
C20—C19—C18—C17	178.0 (2)	C2—C1—O1—C8	−52.41 (12)
C19—C18—C17—C16	0.0 (3)	C23—C1—O1—C8	53.15 (12)
C22—C16—C17—C18	2.3 (3)	C9—C8—O1—C1	−176.06 (12)
C1—C16—C17—C18	−178.81 (16)	C7—C8—O1—C1	53.18 (12)
O1—C8—C9—C10	−102.59 (18)	C26—C8—O1—C1	−51.92 (12)
C7—C8—C9—C10	14.1 (2)	O4—C27—O5—C28	−2.1 (3)
C26—C8—C9—C10	145.51 (17)	C26—C27—O5—C28	173.95 (16)
O1—C8—C9—C15	72.50 (18)	O2—C24—O3—C25	5.0 (3)
C7—C8—C9—C15	−170.83 (15)	C23—C24—O3—C25	−176.13 (17)
C26—C8—C9—C15	−39.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O3ⁱ	0.96	2.56	3.461 (3)	157
C28—H28B···O3ⁱⁱ	0.96	2.52	3.478 (3)	173

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄O₅
M_r	440.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.9018 (4), 25.6357 (8), 11.0961 (4)
β (°)	113.369 (1)
V (Å³)	2324.46 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	29434, 6904, 4338
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.170, 1.03
No. of reflections	6904
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.17

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O3ⁱ	0.96	2.56	3.461 (3)	157
C28—H28B···O3ⁱⁱ	0.96	2.52	3.478 (3)	173

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z.

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

Bailey, J. H., Coulter, C. V., Pratt, A. J. & Robinson, W. T. (1995). J. Chem. Soc. Perkin Trans. 1, pp. 589–592. CrossRef Web of Science Google Scholar
Balakrishnan, B., Nandakumar, M., Seshadri, P. R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o323. CSD CrossRef IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Denmark, S. E. & Thorarensen, A. (1996). Chem. Rev. 96, 137–166. CrossRef PubMed CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takahashi, I., Tsuzuki, M., Kitajima, H., Hetanaka, M., Maeda, S., Yamano, A., Ohta, T. & Hosoi, S. (2003). Anal. Sci. 19, 973–974. Web of Science CSD CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­methyl 1,8-bis­­(4-methyl­phen­yl)-11-oxatri­cyclo­[6.2.1.02,7]undeca-2,4,6,9-tetra­ene-9,10-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Dimethyl 1,8-bis(4-methylphenyl)-11-oxatricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylate