5,5',7,7'-Tetra-meth-oxy-2,2'-ethano-1,1'-spiro-biindane.

In the title compound, C(23)H(26)O(4), there is a dihedral angle of 83.7 (6)° between the two benzene rings. The five-membered rings have chair conformations.

Related literature

For related literature, see: Bandin et al. (2000 ▶); Birman et al. (1999 ▶); Lan et al. (2006 ▶); Zhu et al. (2005 ▶).

Experimental

Crystal data

C23H26O4

M = 366.44

Monoclinic,

a = 12.7089 (11) Å

b = 10.0905 (8) Å

c = 16.1664 (13) Å

β = 104.306 (2)°

V = 2008.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.33 × 0.21 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.974, T max = 0.988

9884 measured reflections

3576 independent reflections

2013 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.08

3576 reflections

249 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.10 e Å−3

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: SHELXTL (Bruker, 2004 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000652/cs2064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000652/cs2064Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H26O4	F000 = 784
Mr = 366.44	Dx = 1.212 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3576 reflections
a = 12.7089 (11) Å	θ = 1.7–25.1º
b = 10.0905 (8) Å	µ = 0.08 mm−1
c = 16.1664 (13) Å	T = 298 (2) K
β = 104.306 (2)º	Block, colourless
V = 2008.9 (3) Å3	0.33 × 0.21 × 0.15 mm
Z = 4

Bruker APEXII area-detector diffractometer	3576 independent reflections
Radiation source: fine-focus sealed tube	2013 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 298(2) K	θmax = 25.1º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −15→15
Tmin = 0.974, Tmax = 0.988	k = −12→11
9884 measured reflections	l = −11→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0439P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.101	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.13 e Å−3
3576 reflections	Δρmin = −0.10 e Å−3
249 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0095 (8)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
O1	0.01787 (11)	0.00651 (13)	0.11905 (9)	0.0934 (5)
O2	0.11557 (9)	0.45860 (11)	0.10743 (7)	0.0615 (3)
O3	0.26734 (10)	0.31122 (11)	−0.09967 (7)	0.0720 (4)
O4	0.21271 (10)	0.76096 (12)	−0.18685 (8)	0.0753 (4)
C1	0.48840 (15)	0.4601 (2)	0.18491 (13)	0.0857 (6)
H1A	0.5280	0.5093	0.1508	0.103*
H1B	0.5161	0.4837	0.2445	0.103*
C2	0.49705 (15)	0.3121 (2)	0.17181 (13)	0.0844 (6)
H2A	0.4716	0.2625	0.2145	0.101*
H2B	0.5713	0.2865	0.1743	0.101*
C3	0.42396 (14)	0.28916 (18)	0.08308 (11)	0.0666 (5)
H3	0.4621	0.3118	0.0392	0.080*
C4	0.37550 (15)	0.14983 (17)	0.06805 (12)	0.0730 (6)
H4A	0.3700	0.1214	0.0098	0.088*
H4B	0.4198	0.0866	0.1068	0.088*
C5	0.26458 (14)	0.16203 (17)	0.08514 (10)	0.0574 (5)
C6	0.19459 (17)	0.06072 (17)	0.09508 (11)	0.0671 (5)
H6	0.2143	−0.0277	0.0930	0.081*
C7	0.09506 (15)	0.09546 (18)	0.10816 (11)	0.0641 (5)
C8	0.06579 (14)	0.22698 (17)	0.11182 (10)	0.0597 (5)
H8	−0.0019	0.2483	0.1204	0.072*
C9	0.13625 (13)	0.32636 (15)	0.10281 (10)	0.0505 (4)
C10	0.23758 (13)	0.29369 (15)	0.08937 (9)	0.0496 (4)
C11	0.32709 (12)	0.38749 (16)	0.07973 (9)	0.0514 (4)
C12	0.29743 (12)	0.47861 (16)	0.00341 (10)	0.0503 (4)
C13	0.26767 (13)	0.44407 (16)	−0.08266 (10)	0.0517 (4)
C14	0.24065 (13)	0.54127 (17)	−0.14428 (10)	0.0566 (5)
H14	0.2207	0.5184	−0.2018	0.068*
C15	0.24339 (13)	0.67340 (17)	−0.11997 (11)	0.0571 (5)
C16	0.27449 (13)	0.71002 (16)	−0.03510 (12)	0.0604 (5)
H16	0.2774	0.7988	−0.0192	0.072*
C17	0.30128 (13)	0.61047 (17)	0.02569 (10)	0.0543 (4)
C18	0.33526 (15)	0.62685 (17)	0.12096 (11)	0.0685 (5)
H18A	0.2758	0.6610	0.1425	0.082*
H18B	0.3964	0.6870	0.1373	0.082*
C19	0.36713 (14)	0.48682 (17)	0.15539 (10)	0.0619 (5)
H19	0.3321	0.4665	0.2015	0.074*
C20	0.03804 (18)	−0.13115 (18)	0.11287 (13)	0.0989 (7)
H20A	0.0585	−0.1485	0.0606	0.148*
H20B	−0.0265	−0.1801	0.1135	0.148*
H20C	0.0957	−0.1578	0.1604	0.148*
C21	0.01061 (14)	0.49516 (17)	0.11711 (13)	0.0794 (6)
H21A	−0.0442	0.4600	0.0704	0.119*
H21B	0.0049	0.5900	0.1176	0.119*
H21C	0.0006	0.4600	0.1698	0.119*
C22	0.2423 (2)	0.27137 (19)	−0.18592 (13)	0.1168 (9)
H22A	0.1692	0.2970	−0.2132	0.175*
H22B	0.2491	0.1769	−0.1890	0.175*
H22C	0.2915	0.3131	−0.2143	0.175*
C23	0.22177 (17)	0.89829 (17)	−0.16809 (13)	0.0850 (6)
H23A	0.1752	0.9208	−0.1316	0.127*
H23B	0.2006	0.9480	−0.2202	0.127*
H23C	0.2956	0.9190	−0.1398	0.127*

	U11	U22	U33	U12	U13	U23
O1	0.0960 (11)	0.0534 (9)	0.1336 (13)	−0.0154 (7)	0.0338 (9)	−0.0010 (8)
O2	0.0575 (8)	0.0496 (8)	0.0802 (8)	0.0036 (6)	0.0222 (6)	−0.0009 (6)
O3	0.1176 (11)	0.0527 (8)	0.0469 (8)	0.0052 (7)	0.0223 (7)	−0.0020 (6)
O4	0.0980 (10)	0.0589 (9)	0.0687 (9)	0.0035 (7)	0.0202 (7)	0.0151 (7)
C1	0.0645 (14)	0.1059 (18)	0.0789 (15)	−0.0058 (12)	0.0033 (11)	−0.0021 (12)
C2	0.0551 (12)	0.1137 (18)	0.0815 (15)	0.0141 (11)	0.0117 (11)	0.0149 (13)
C3	0.0684 (13)	0.0810 (14)	0.0559 (12)	0.0144 (10)	0.0260 (10)	0.0110 (10)
C4	0.0853 (15)	0.0739 (14)	0.0629 (12)	0.0268 (11)	0.0244 (10)	0.0095 (10)
C5	0.0708 (13)	0.0570 (12)	0.0452 (10)	0.0114 (10)	0.0158 (9)	0.0050 (8)
C6	0.0936 (15)	0.0490 (11)	0.0570 (12)	0.0103 (11)	0.0150 (10)	0.0018 (9)
C7	0.0725 (14)	0.0558 (13)	0.0621 (12)	−0.0061 (10)	0.0130 (10)	0.0008 (9)
C8	0.0612 (12)	0.0526 (12)	0.0639 (12)	0.0025 (9)	0.0129 (9)	0.0014 (9)
C9	0.0619 (12)	0.0422 (11)	0.0453 (10)	0.0049 (9)	0.0093 (8)	0.0016 (8)
C10	0.0590 (11)	0.0530 (11)	0.0365 (9)	0.0064 (8)	0.0114 (8)	0.0041 (7)
C11	0.0552 (10)	0.0601 (11)	0.0411 (10)	0.0052 (9)	0.0160 (8)	0.0031 (8)
C12	0.0525 (10)	0.0556 (11)	0.0446 (10)	−0.0001 (8)	0.0152 (8)	0.0001 (8)
C13	0.0617 (11)	0.0474 (11)	0.0487 (11)	0.0002 (8)	0.0188 (8)	−0.0004 (8)
C14	0.0679 (12)	0.0579 (12)	0.0459 (10)	−0.0014 (9)	0.0178 (8)	0.0029 (9)
C15	0.0644 (12)	0.0541 (12)	0.0558 (12)	0.0005 (9)	0.0208 (9)	0.0129 (10)
C16	0.0721 (12)	0.0498 (11)	0.0639 (13)	−0.0045 (9)	0.0256 (10)	−0.0033 (10)
C17	0.0582 (11)	0.0578 (12)	0.0496 (11)	−0.0054 (8)	0.0183 (9)	−0.0032 (9)
C18	0.0790 (13)	0.0717 (13)	0.0561 (12)	−0.0113 (10)	0.0190 (10)	−0.0101 (9)
C19	0.0584 (12)	0.0783 (13)	0.0483 (10)	−0.0052 (10)	0.0119 (9)	−0.0031 (9)
C20	0.1240 (19)	0.0513 (14)	0.1129 (18)	−0.0128 (12)	0.0132 (15)	0.0006 (11)
C21	0.0659 (13)	0.0621 (13)	0.1158 (17)	0.0110 (10)	0.0329 (12)	−0.0006 (11)
C22	0.235 (3)	0.0622 (14)	0.0548 (14)	−0.0128 (15)	0.0381 (16)	−0.0153 (10)
C23	0.1083 (17)	0.0570 (14)	0.0975 (16)	0.0083 (11)	0.0403 (13)	0.0200 (11)

O1—C7	1.373 (2)	C10—C11	1.517 (2)
O1—C20	1.420 (2)	C11—C12	1.510 (2)
O2—C9	1.3656 (17)	C11—C19	1.566 (2)
O2—C21	1.4294 (18)	C12—C17	1.376 (2)
O3—C13	1.3682 (18)	C12—C13	1.393 (2)
O3—C22	1.410 (2)	C13—C14	1.380 (2)
O4—C15	1.3759 (19)	C14—C15	1.388 (2)
O4—C23	1.4171 (19)	C14—H14	0.9300
C1—C2	1.516 (3)	C15—C16	1.381 (2)
C1—C19	1.521 (2)	C16—C17	1.388 (2)
C1—H1A	0.9700	C16—H16	0.9300
C1—H1B	0.9700	C17—C18	1.502 (2)
C2—C3	1.522 (2)	C18—C19	1.536 (2)
C2—H2A	0.9700	C18—H18A	0.9700
C2—H2B	0.9700	C18—H18B	0.9700
C3—C4	1.530 (2)	C19—H19	0.9800
C3—C11	1.572 (2)	C20—H20A	0.9600
C3—H3	0.9800	C20—H20B	0.9600
C4—C5	1.507 (2)	C20—H20C	0.9600
C4—H4A	0.9700	C21—H21A	0.9600
C4—H4B	0.9700	C21—H21B	0.9600
C5—C10	1.378 (2)	C21—H21C	0.9600
C5—C6	1.390 (2)	C22—H22A	0.9600
C6—C7	1.378 (2)	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
C7—C8	1.383 (2)	C23—H23A	0.9600
C8—C9	1.376 (2)	C23—H23B	0.9600
C8—H8	0.9300	C23—H23C	0.9600
C9—C10	1.397 (2)
C7—O1—C20	118.91 (16)	C17—C12—C11	112.92 (14)
C9—O2—C21	117.11 (13)	C13—C12—C11	127.96 (15)
C13—O3—C22	117.84 (13)	O3—C13—C14	124.30 (15)
C15—O4—C23	117.87 (15)	O3—C13—C12	115.63 (14)
C2—C1—C19	103.52 (16)	C14—C13—C12	120.07 (15)
C2—C1—H1A	111.1	C13—C14—C15	119.61 (15)
C19—C1—H1A	111.1	C13—C14—H14	120.2
C2—C1—H1B	111.1	C15—C14—H14	120.2
C19—C1—H1B	111.1	O4—C15—C16	124.39 (16)
H1A—C1—H1B	109.0	O4—C15—C14	114.33 (16)
C1—C2—C3	103.46 (15)	C16—C15—C14	121.29 (15)
C1—C2—H2A	111.1	C15—C16—C17	118.02 (15)
C3—C2—H2A	111.1	C15—C16—H16	121.0
C1—C2—H2B	111.1	C17—C16—H16	121.0
C3—C2—H2B	111.1	C12—C17—C16	121.87 (15)
H2A—C2—H2B	109.0	C12—C17—C18	110.93 (15)
C2—C3—C4	114.65 (15)	C16—C17—C18	127.19 (16)
C2—C3—C11	103.13 (14)	C17—C18—C19	104.68 (14)
C4—C3—C11	107.07 (14)	C17—C18—H18A	110.8
C2—C3—H3	110.6	C19—C18—H18A	110.8
C4—C3—H3	110.6	C17—C18—H18B	110.8
C11—C3—H3	110.6	C19—C18—H18B	110.8
C5—C4—C3	104.71 (14)	H18A—C18—H18B	108.9
C5—C4—H4A	110.8	C1—C19—C18	115.66 (15)
C3—C4—H4A	110.8	C1—C19—C11	103.89 (14)
C5—C4—H4B	110.8	C18—C19—C11	107.47 (13)
C3—C4—H4B	110.8	C1—C19—H19	109.9
H4A—C4—H4B	108.9	C18—C19—H19	109.9
C10—C5—C6	121.93 (16)	C11—C19—H19	109.9
C10—C5—C4	110.09 (16)	O1—C20—H20A	109.5
C6—C5—C4	127.97 (16)	O1—C20—H20B	109.5
C7—C6—C5	117.93 (16)	H20A—C20—H20B	109.5
C7—C6—H6	121.0	O1—C20—H20C	109.5
C5—C6—H6	121.0	H20A—C20—H20C	109.5
O1—C7—C6	124.43 (17)	H20B—C20—H20C	109.5
O1—C7—C8	114.43 (17)	O2—C21—H21A	109.5
C6—C7—C8	121.14 (17)	O2—C21—H21B	109.5
C9—C8—C7	120.37 (16)	H21A—C21—H21B	109.5
C9—C8—H8	119.8	O2—C21—H21C	109.5
C7—C8—H8	119.8	H21A—C21—H21C	109.5
O2—C9—C8	124.55 (15)	H21B—C21—H21C	109.5
O2—C9—C10	115.87 (14)	O3—C22—H22A	109.5
C8—C9—C10	119.57 (15)	O3—C22—H22B	109.5
C5—C10—C9	119.04 (15)	H22A—C22—H22B	109.5
C5—C10—C11	113.21 (14)	O3—C22—H22C	109.5
C9—C10—C11	127.74 (14)	H22A—C22—H22C	109.5
C12—C11—C10	114.94 (13)	H22B—C22—H22C	109.5
C12—C11—C19	102.46 (13)	O4—C23—H23A	109.5
C10—C11—C19	115.23 (12)	O4—C23—H23B	109.5
C12—C11—C3	116.61 (12)	H23A—C23—H23B	109.5
C10—C11—C3	101.74 (13)	O4—C23—H23C	109.5
C19—C11—C3	106.06 (13)	H23A—C23—H23C	109.5
C17—C12—C13	119.12 (14)	H23B—C23—H23C	109.5
C19—C1—C2—C3	45.85 (18)	C10—C11—C12—C17	117.93 (15)
C1—C2—C3—C4	−153.35 (15)	C19—C11—C12—C17	−7.82 (17)
C1—C2—C3—C11	−37.33 (18)	C3—C11—C12—C17	−123.13 (16)
C2—C3—C4—C5	95.86 (17)	C10—C11—C12—C13	−61.8 (2)
C11—C3—C4—C5	−17.87 (17)	C19—C11—C12—C13	172.49 (15)
C3—C4—C5—C10	12.87 (18)	C3—C11—C12—C13	57.2 (2)
C3—C4—C5—C6	−167.74 (16)	C22—O3—C13—C14	2.9 (2)
C10—C5—C6—C7	1.0 (2)	C22—O3—C13—C12	−177.36 (17)
C4—C5—C6—C7	−178.31 (17)	C17—C12—C13—O3	179.06 (14)
C20—O1—C7—C6	−3.0 (3)	C11—C12—C13—O3	−1.3 (2)
C20—O1—C7—C8	177.41 (15)	C17—C12—C13—C14	−1.2 (2)
C5—C6—C7—O1	−179.96 (16)	C11—C12—C13—C14	178.52 (15)
C5—C6—C7—C8	−0.4 (3)	O3—C13—C14—C15	179.81 (15)
O1—C7—C8—C9	179.30 (14)	C12—C13—C14—C15	0.0 (2)
C6—C7—C8—C9	−0.3 (3)	C23—O4—C15—C16	5.2 (2)
C21—O2—C9—C8	−4.0 (2)	C23—O4—C15—C14	−174.92 (14)
C21—O2—C9—C10	177.12 (14)	C13—C14—C15—O4	−178.73 (14)
C7—C8—C9—O2	−178.43 (15)	C13—C14—C15—C16	1.1 (2)
C7—C8—C9—C10	0.4 (2)	O4—C15—C16—C17	178.73 (15)
C6—C5—C10—C9	−0.9 (2)	C14—C15—C16—C17	−1.1 (2)
C4—C5—C10—C9	178.50 (14)	C13—C12—C17—C16	1.2 (2)
C6—C5—C10—C11	178.08 (14)	C11—C12—C17—C16	−178.55 (14)
C4—C5—C10—C11	−2.48 (18)	C13—C12—C17—C18	−179.81 (14)
O2—C9—C10—C5	179.15 (13)	C11—C12—C17—C18	0.47 (19)
C8—C9—C10—C5	0.2 (2)	C15—C16—C17—C12	−0.1 (2)
O2—C9—C10—C11	0.3 (2)	C15—C16—C17—C18	−178.90 (16)
C8—C9—C10—C11	−178.65 (14)	C12—C17—C18—C19	7.32 (19)
C5—C10—C11—C12	118.32 (15)	C16—C17—C18—C19	−173.73 (16)
C9—C10—C11—C12	−62.8 (2)	C2—C1—C19—C18	−152.31 (15)
C5—C10—C11—C19	−122.85 (14)	C2—C1—C19—C11	−34.81 (18)
C9—C10—C11—C19	56.1 (2)	C17—C18—C19—C1	103.58 (17)
C5—C10—C11—C3	−8.63 (16)	C17—C18—C19—C11	−11.91 (17)
C9—C10—C11—C3	170.29 (15)	C12—C11—C19—C1	−111.14 (14)
C2—C3—C11—C12	128.93 (16)	C10—C11—C19—C1	123.31 (15)
C4—C3—C11—C12	−109.76 (16)	C3—C11—C19—C1	11.61 (17)
C2—C3—C11—C10	−105.22 (15)	C12—C11—C19—C18	11.92 (16)
C4—C3—C11—C10	16.09 (16)	C10—C11—C19—C18	−113.63 (15)
C2—C3—C11—C19	15.64 (17)	C3—C11—C19—C18	134.67 (14)
C4—C3—C11—C19	136.95 (13)