Diethyl 9,10-di­hydro-9,10-ethano­anthracene-11,12-trans-di­carboxyl­ate

The title compound, C₂₂H₂₂O₄, is the product of the Diels-Alder reaction of anthracene with fumaric acid diethyl ester. The molecular C₂ symmetry is nearly fulfilled in the crystal. Only the terminal torsion angles about the O-CH₂ groups show significant differences.

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

;

Crystal data

C22H22O4	F(000) = 744
Mr = 350.40	Dx = 1.267 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.8786 (7) Å	Cell parameters from 510 reflections
b = 18.417 (1) Å	θ = 1–20°
c = 12.758 (1) Å	µ = 0.09 mm^−1
β = 96.971 (5)°	T = 173 K
V = 1837.5 (2) Å^3	Block, colourless
Z = 4	0.70 × 0.50 × 0.50 mm

Data collection

Siemens CCD three-circle diffractometer	4656 independent reflections
Radiation source: fine-focus sealed tube	4052 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 29.6°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.942, Tmax = 0.958	k = −22→25
34998 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 0.9045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4656 reflections	Δρmax = 0.55 e Å^−3
236 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0147 (16)

Special details

Experimental. ;

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.38111 (16)	0.59519 (7)	0.13420 (9)	0.0240 (3)
H1	0.3211	0.5675	0.0732	0.029*
C2	0.43939 (16)	0.66933 (7)	0.10161 (9)	0.0242 (2)
C3	0.41512 (17)	0.69909 (8)	0.00107 (10)	0.0297 (3)
H3	0.3542	0.6729	−0.0557	0.036*
C4	0.48097 (19)	0.76782 (8)	−0.01596 (12)	0.0357 (3)
H4	0.4668	0.7881	−0.0849	0.043*
C5	0.56684 (19)	0.80667 (8)	0.06711 (12)	0.0361 (3)
H5	0.6092	0.8539	0.0551	0.043*
C6	0.59141 (18)	0.77681 (7)	0.16847 (11)	0.0313 (3)
H6	0.6508	0.8034	0.2254	0.038*
C7	0.52841 (16)	0.70808 (7)	0.18522 (10)	0.0250 (3)
C8	0.54884 (16)	0.66680 (7)	0.28887 (9)	0.0245 (3)
H8	0.6175	0.6946	0.3466	0.029*
C9	0.63006 (16)	0.59444 (7)	0.26816 (10)	0.0249 (3)
C10	0.78081 (17)	0.56647 (8)	0.32041 (11)	0.0314 (3)
H10	0.8405	0.5918	0.3784	0.038*
C11	0.84345 (19)	0.50087 (8)	0.28677 (13)	0.0370 (3)
H11	0.9475	0.4817	0.3212	0.044*
C12	0.75461 (19)	0.46345 (8)	0.20331 (12)	0.0363 (3)
H12	0.7992	0.4191	0.1803	0.044*
C13	0.60059 (18)	0.49010 (7)	0.15270 (11)	0.0306 (3)
H13	0.5384	0.4635	0.0969	0.037*
C14	0.53918 (16)	0.55603 (7)	0.18489 (10)	0.0248 (3)
C15	0.26295 (16)	0.60938 (7)	0.22189 (9)	0.0250 (3)
H15	0.2269	0.5614	0.2484	0.030*
C16	0.36417 (16)	0.65043 (7)	0.31507 (9)	0.0242 (3)
H16	0.3058	0.6980	0.3228	0.029*
C51	0.10326 (17)	0.65088 (8)	0.17813 (10)	0.0305 (3)
O51	0.04149 (14)	0.70085 (7)	0.22068 (9)	0.0466 (3)
O52	0.03809 (13)	0.62427 (7)	0.08508 (8)	0.0409 (3)
C53	−0.1162 (2)	0.65981 (13)	0.03503 (13)	0.0552 (5)
H53A	−0.2131	0.6497	0.0756	0.066*
H53B	−0.0986	0.7130	0.0335	0.066*
C54	−0.1541 (3)	0.63215 (17)	−0.07192 (17)	0.0811 (9)
H54A	−0.2564	0.6563	−0.1070	0.122*
H54B	−0.1743	0.5797	−0.0696	0.122*
H54C	−0.0571	0.6418	−0.1113	0.122*
C61	0.36465 (17)	0.60932 (7)	0.41834 (10)	0.0269 (3)
O61	0.26785 (15)	0.56111 (6)	0.43353 (8)	0.0416 (3)
O62	0.48275 (14)	0.63583 (6)	0.49145 (8)	0.0386 (3)
C63	0.4992 (2)	0.60234 (11)	0.59578 (12)	0.0467 (4)
H63A	0.4739	0.5498	0.5894	0.056*
H63B	0.4176	0.6248	0.6394	0.056*
C64	0.6758 (3)	0.61366 (12)	0.64529 (14)	0.0547 (5)
H64A	0.6902	0.5917	0.7158	0.082*
H64B	0.6995	0.6658	0.6513	0.082*
H64C	0.7554	0.5910	0.6018	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0256 (6)	0.0248 (6)	0.0215 (5)	0.0004 (4)	0.0027 (4)	−0.0013 (4)
C2	0.0233 (6)	0.0259 (6)	0.0241 (5)	0.0034 (4)	0.0061 (4)	0.0006 (4)
C3	0.0305 (7)	0.0346 (7)	0.0247 (6)	0.0072 (5)	0.0061 (5)	0.0034 (5)
C4	0.0380 (7)	0.0381 (7)	0.0330 (7)	0.0095 (6)	0.0126 (6)	0.0129 (6)
C5	0.0383 (8)	0.0280 (7)	0.0447 (8)	0.0021 (5)	0.0159 (6)	0.0089 (6)
C6	0.0327 (7)	0.0265 (6)	0.0362 (7)	−0.0014 (5)	0.0099 (5)	−0.0003 (5)
C7	0.0247 (6)	0.0256 (6)	0.0255 (6)	0.0013 (5)	0.0066 (4)	0.0008 (4)
C8	0.0257 (6)	0.0261 (6)	0.0217 (5)	−0.0034 (5)	0.0027 (4)	−0.0010 (4)
C9	0.0254 (6)	0.0261 (6)	0.0239 (5)	−0.0013 (5)	0.0055 (5)	0.0032 (4)
C10	0.0268 (6)	0.0354 (7)	0.0312 (6)	−0.0031 (5)	0.0007 (5)	0.0067 (5)
C11	0.0284 (7)	0.0377 (8)	0.0448 (8)	0.0056 (6)	0.0039 (6)	0.0130 (6)
C12	0.0382 (8)	0.0288 (7)	0.0435 (8)	0.0088 (6)	0.0111 (6)	0.0054 (6)
C13	0.0355 (7)	0.0264 (6)	0.0306 (6)	0.0018 (5)	0.0070 (5)	0.0010 (5)
C14	0.0258 (6)	0.0249 (6)	0.0242 (5)	0.0004 (5)	0.0055 (5)	0.0023 (4)
C15	0.0251 (6)	0.0281 (6)	0.0221 (5)	−0.0022 (5)	0.0037 (4)	−0.0008 (4)
C16	0.0260 (6)	0.0263 (6)	0.0207 (5)	0.0004 (5)	0.0041 (4)	−0.0005 (4)
C51	0.0243 (6)	0.0435 (8)	0.0242 (6)	−0.0007 (5)	0.0056 (5)	−0.0006 (5)
O51	0.0389 (6)	0.0605 (8)	0.0391 (6)	0.0175 (5)	−0.0004 (5)	−0.0109 (5)
O52	0.0257 (5)	0.0651 (7)	0.0304 (5)	0.0070 (5)	−0.0023 (4)	−0.0115 (5)
C53	0.0289 (8)	0.0993 (15)	0.0356 (8)	0.0193 (9)	−0.0038 (6)	−0.0097 (9)
C54	0.0559 (12)	0.137 (2)	0.0459 (11)	0.0379 (14)	−0.0131 (9)	−0.0235 (13)
C61	0.0279 (6)	0.0314 (6)	0.0223 (5)	0.0022 (5)	0.0064 (5)	−0.0002 (5)
O61	0.0510 (7)	0.0448 (6)	0.0294 (5)	−0.0144 (5)	0.0061 (4)	0.0047 (4)
O62	0.0374 (6)	0.0547 (7)	0.0225 (5)	−0.0114 (5)	−0.0009 (4)	0.0068 (4)
C63	0.0413 (8)	0.0735 (12)	0.0247 (7)	−0.0029 (8)	0.0010 (6)	0.0151 (7)
C64	0.0564 (11)	0.0637 (12)	0.0396 (9)	−0.0084 (9)	−0.0120 (8)	0.0080 (8)

Geometric parameters (Å, º)

C1—C14	1.5145 (17)	C13—C14	1.3874 (18)
C1—C2	1.5149 (17)	C13—H13	0.9500
C1—C15	1.5619 (17)	C15—C51	1.5193 (18)
C1—H1	1.0000	C15—C16	1.5461 (17)
C2—C3	1.3866 (17)	C15—H15	1.0000
C2—C7	1.3991 (17)	C16—C61	1.5191 (17)
C3—C4	1.395 (2)	C16—H16	1.0000
C3—H3	0.9500	C51—O51	1.2012 (18)
C4—C5	1.385 (2)	C51—O52	1.3286 (16)
C4—H4	0.9500	O52—C53	1.4580 (19)
C5—C6	1.397 (2)	C53—C54	1.453 (3)
C5—H5	0.9500	C53—H53A	0.9900
C6—C7	1.3857 (18)	C53—H53B	0.9900
C6—H6	0.9500	C54—H54A	0.9800
C7—C8	1.5169 (17)	C54—H54B	0.9800
C8—C9	1.5153 (17)	C54—H54C	0.9800
C8—C16	1.5613 (17)	C61—O61	1.2013 (17)
C8—H8	1.0000	C61—O62	1.3280 (16)
C9—C10	1.3885 (18)	O62—C63	1.4584 (17)
C9—C14	1.3991 (17)	C63—C64	1.472 (2)
C10—C11	1.392 (2)	C63—H63A	0.9900
C10—H10	0.9500	C63—H63B	0.9900
C11—C12	1.385 (2)	C64—H64A	0.9800
C11—H11	0.9500	C64—H64B	0.9800
C12—C13	1.393 (2)	C64—H64C	0.9800
C12—H12	0.9500
C14—C1—C2	106.59 (10)	C13—C14—C1	126.05 (12)
C14—C1—C15	107.73 (10)	C9—C14—C1	113.70 (11)
C2—C1—C15	105.82 (10)	C51—C15—C16	111.31 (11)
C14—C1—H1	112.1	C51—C15—C1	111.10 (10)
C2—C1—H1	112.1	C16—C15—C1	109.63 (10)
C15—C1—H1	112.1	C51—C15—H15	108.2
C3—C2—C7	120.25 (12)	C16—C15—H15	108.2
C3—C2—C1	126.71 (12)	C1—C15—H15	108.2
C7—C2—C1	113.02 (10)	C61—C16—C15	111.71 (10)
C2—C3—C4	119.38 (13)	C61—C16—C8	112.18 (10)
C2—C3—H3	120.3	C15—C16—C8	109.69 (10)
C4—C3—H3	120.3	C61—C16—H16	107.7
C5—C4—C3	120.38 (13)	C15—C16—H16	107.7
C5—C4—H4	119.8	C8—C16—H16	107.7
C3—C4—H4	119.8	O51—C51—O52	123.55 (13)
C4—C5—C6	120.32 (13)	O51—C51—C15	125.61 (12)
C4—C5—H5	119.8	O52—C51—C15	110.84 (12)
C6—C5—H5	119.8	C51—O52—C53	115.91 (12)
C7—C6—C5	119.37 (13)	C54—C53—O52	108.61 (15)
C7—C6—H6	120.3	C54—C53—H53A	110.0
C5—C6—H6	120.3	O52—C53—H53A	110.0
C6—C7—C2	120.27 (12)	C54—C53—H53B	110.0
C6—C7—C8	126.18 (12)	O52—C53—H53B	110.0
C2—C7—C8	113.54 (11)	H53A—C53—H53B	108.3
C9—C8—C7	106.93 (10)	C53—C54—H54A	109.5
C9—C8—C16	106.96 (10)	C53—C54—H54B	109.5
C7—C8—C16	106.28 (10)	H54A—C54—H54B	109.5
C9—C8—H8	112.1	C53—C54—H54C	109.5
C7—C8—H8	112.1	H54A—C54—H54C	109.5
C16—C8—H8	112.1	H54B—C54—H54C	109.5
C10—C9—C14	120.40 (12)	O61—C61—O62	124.25 (12)
C10—C9—C8	126.67 (12)	O61—C61—C16	124.99 (12)
C14—C9—C8	112.90 (11)	O62—C61—C16	110.71 (11)
C9—C10—C11	119.24 (13)	C61—O62—C63	117.56 (12)
C9—C10—H10	120.4	O62—C63—C64	107.85 (14)
C11—C10—H10	120.4	O62—C63—H63A	110.1
C12—C11—C10	120.26 (13)	C64—C63—H63A	110.1
C12—C11—H11	119.9	O62—C63—H63B	110.1
C10—C11—H11	119.9	C64—C63—H63B	110.1
C11—C12—C13	120.76 (13)	H63A—C63—H63B	108.4
C11—C12—H12	119.6	C63—C64—H64A	109.5
C13—C12—H12	119.6	C63—C64—H64B	109.5
C14—C13—C12	119.13 (13)	H64A—C64—H64B	109.5
C14—C13—H13	120.4	C63—C64—H64C	109.5
C12—C13—H13	120.4	H64A—C64—H64C	109.5
C13—C14—C9	120.17 (12)	H64B—C64—H64C	109.5
C14—C1—C2—C3	123.71 (13)	C10—C9—C14—C1	−178.07 (11)
C15—C1—C2—C3	−121.78 (13)	C8—C9—C14—C1	0.13 (15)
C14—C1—C2—C7	−55.12 (13)	C2—C1—C14—C13	−122.06 (13)
C15—C1—C2—C7	59.39 (13)	C15—C1—C14—C13	124.74 (13)
C7—C2—C3—C4	0.30 (19)	C2—C1—C14—C9	54.75 (13)
C1—C2—C3—C4	−178.45 (12)	C15—C1—C14—C9	−58.45 (13)
C2—C3—C4—C5	−1.3 (2)	C14—C1—C15—C51	178.15 (10)
C3—C4—C5—C6	1.3 (2)	C2—C1—C15—C51	64.43 (13)
C4—C5—C6—C7	−0.3 (2)	C14—C1—C15—C16	54.70 (13)
C5—C6—C7—C2	−0.7 (2)	C2—C1—C15—C16	−59.02 (12)
C5—C6—C7—C8	177.83 (12)	C51—C15—C16—C61	113.84 (12)
C3—C2—C7—C6	0.70 (19)	C1—C15—C16—C61	−122.84 (11)
C1—C2—C7—C6	179.61 (11)	C51—C15—C16—C8	−121.13 (11)
C3—C2—C7—C8	−178.01 (11)	C1—C15—C16—C8	2.20 (14)
C1—C2—C7—C8	0.91 (15)	C9—C8—C16—C61	66.45 (12)
C6—C7—C8—C9	−124.54 (13)	C7—C8—C16—C61	−179.59 (10)
C2—C7—C8—C9	54.08 (14)	C9—C8—C16—C15	−58.32 (12)
C6—C7—C8—C16	121.47 (13)	C7—C8—C16—C15	55.65 (13)
C2—C7—C8—C16	−59.91 (13)	C16—C15—C51—O51	−14.2 (2)
C7—C8—C9—C10	123.60 (13)	C1—C15—C51—O51	−136.67 (15)
C16—C8—C9—C10	−122.87 (13)	C16—C15—C51—O52	166.16 (11)
C7—C8—C9—C14	−54.46 (13)	C1—C15—C51—O52	43.68 (15)
C16—C8—C9—C14	59.06 (13)	O51—C51—O52—C53	0.3 (2)
C14—C9—C10—C11	2.06 (19)	C15—C51—O52—C53	179.97 (14)
C8—C9—C10—C11	−175.87 (12)	C51—O52—C53—C54	171.00 (19)
C9—C10—C11—C12	−1.1 (2)	C15—C16—C61—O61	−17.07 (19)
C10—C11—C12—C13	−0.9 (2)	C8—C16—C61—O61	−140.71 (14)
C11—C12—C13—C14	1.9 (2)	C15—C16—C61—O62	165.42 (11)
C12—C13—C14—C9	−0.94 (19)	C8—C16—C61—O62	41.78 (15)
C12—C13—C14—C1	175.69 (12)	O61—C61—O62—C63	2.2 (2)
C10—C9—C14—C13	−1.05 (19)	C16—C61—O62—C63	179.73 (13)
C8—C9—C14—C13	177.15 (11)	C61—O62—C63—C64	153.80 (15)