9,17-Dioxa-1,3-di­thia­tetra­cyclo­[18.2.2.2^23,24.1²⁵]­heptacosa-5,7,11,13,15-(25),18,20,23,26-nonene

The title compound, C₂₃H₂₂O₂S₂, consists of an m-xyl­ene moiety symmetrically linked by phenoxymethyl groups, which are bridged by a methanedi­thiol unit. The two benzene rings at the dithio end of the molecule are almost perpendicular to each other [87.1 (1)°]. The crystal packing is stabilized by C—H...π and weak π...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.127
• Data-to-parameter ratio = 23.8

checkCIF/PLATON results

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Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

9, 17-Dioxa-1,3-dithiatetracyclo[18. 2. 2. 2^{23, 24}. 1²⁵] heptacosan-5, 7, 11,13, 15 (25), 18, 20, 23, 26 nonene

Crystal data

C23H22O2S2	Z = 2
Mr = 394.53	F(000) = 416
Triclinic, P1	Dx = 1.306 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.995 (5) Å	Cell parameters from 25 reflections
b = 10.372 (7) Å	θ = 1.8–12.6°
c = 10.508 (5) Å	µ = 0.28 mm^−1
α = 101.84 (5)°	T = 293 K
β = 91.14 (5)°	Block, colourless
γ = 109.01 (5)°	0.46 × 0.29 × 0.28 mm
V = 1003.5 (10) Å^3

Data collection

Enraf Nonius FR590 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.0°
Graphite monochromator	h = −14→13
non–profiled w/2θ scans	k = 0→14
6133 measured reflections	l = −14→14
5832 independent reflections	3 standard reflections every 200 reflections
3032 reflections with I > 2σ(I)	intensity decay: 3%

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0631P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5832 reflections	Δρmax = 0.21 e Å^−3
245 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.070 (4)

Special details

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
S1	−0.37039 (5)	−0.18755 (6)	0.59690 (6)	0.06067 (18)
S2	−0.21438 (6)	−0.38690 (6)	0.52576 (5)	0.05563 (17)
O1	0.08204 (13)	0.39596 (13)	0.97943 (12)	0.0515 (3)
O2	0.42171 (14)	0.02889 (15)	0.82650 (17)	0.0660 (4)
C1	0.33671 (18)	0.33670 (19)	0.93297 (18)	0.0441 (4)
H1	0.2881	0.3051	1.0013	0.053*
C2	0.43220 (18)	0.27419 (19)	0.87843 (18)	0.0437 (4)
C3	0.50688 (19)	0.3252 (2)	0.77861 (19)	0.0510 (5)
H3	0.5712	0.2850	0.7402	0.061*
C4	0.4858 (2)	0.4351 (2)	0.7366 (2)	0.0547 (5)
H4	0.5376	0.4701	0.6713	0.066*
C5	0.3879 (2)	0.4939 (2)	0.79078 (19)	0.0509 (5)
H5	0.3736	0.5672	0.7608	0.061*
C6	0.31161 (18)	0.44420 (18)	0.88901 (18)	0.0429 (4)
C7	0.2003 (2)	0.5014 (2)	0.9476 (2)	0.0535 (5)
H7A	0.2430	0.5730	1.0260	0.064*
H7B	0.1672	0.5450	0.8861	0.064*
C8	−0.01096 (18)	0.30194 (19)	0.87890 (17)	0.0423 (4)
C9	−0.0037 (2)	0.3030 (2)	0.74767 (18)	0.0496 (5)
H9	0.0700	0.3705	0.7209	0.060*
C10	−0.1075 (2)	0.2025 (2)	0.65635 (18)	0.0514 (5)
H10	−0.1023	0.2042	0.5684	0.062*
C11	−0.21866 (18)	0.0995 (2)	0.69210 (17)	0.0438 (4)
C12	−0.22253 (19)	0.1004 (2)	0.82433 (18)	0.0471 (4)
H12	−0.2955	0.0324	0.8513	0.057*
C13	−0.12109 (19)	0.1994 (2)	0.91630 (17)	0.0453 (4)
H13	−0.1264	0.1976	1.0042	0.054*
C14	−0.3349 (2)	−0.0058 (2)	0.5931 (2)	0.0569 (5)
H14A	−0.3098	0.0063	0.5065	0.068*
H14B	−0.4220	0.0153	0.6066	0.068*
C15	−0.22261 (19)	−0.2196 (2)	0.51659 (19)	0.0513 (5)
H15A	−0.2325	−0.2152	0.4257	0.062*
H15B	−0.1348	−0.1473	0.5574	0.062*
C16	−0.1411 (2)	−0.3537 (2)	0.69394 (19)	0.0580 (5)
H16A	−0.2039	−0.3215	0.7516	0.070*
H16B	−0.1392	−0.4411	0.7121	0.070*
C17	0.0065 (2)	−0.2474 (2)	0.72490 (18)	0.0478 (5)
C18	0.1248 (2)	−0.2841 (2)	0.6884 (2)	0.0525 (5)
H18	0.1121	−0.3740	0.6407	0.063*
C19	0.2608 (2)	−0.1888 (2)	0.7222 (2)	0.0528 (5)
H19	0.3386	−0.2152	0.6971	0.063*
C20	0.28187 (19)	−0.0548 (2)	0.7930 (2)	0.0496 (5)
C21	0.1649 (2)	−0.0150 (2)	0.8249 (2)	0.0563 (5)
H21	0.1771	0.0760	0.8691	0.068*
C22	0.0292 (2)	−0.1125 (2)	0.7901 (2)	0.0532 (5)
H22	−0.0488	−0.0852	0.8119	0.064*
C23	0.4525 (2)	0.1549 (2)	0.9260 (2)	0.0580 (5)
H23A	0.5501	0.1827	0.9628	0.070*
H23B	0.3916	0.1356	0.9954	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0414 (3)	0.0625 (4)	0.0653 (4)	0.0087 (2)	0.0102 (2)	0.0002 (3)
S2	0.0542 (3)	0.0573 (3)	0.0473 (3)	0.0124 (3)	0.0042 (2)	0.0047 (2)
O1	0.0454 (7)	0.0561 (8)	0.0477 (8)	0.0186 (6)	0.0019 (6)	−0.0024 (6)
O2	0.0366 (7)	0.0482 (8)	0.1132 (13)	0.0165 (6)	0.0125 (8)	0.0137 (8)
C1	0.0375 (9)	0.0441 (10)	0.0467 (11)	0.0096 (8)	0.0044 (8)	0.0082 (8)
C2	0.0331 (9)	0.0408 (10)	0.0523 (11)	0.0089 (8)	−0.0015 (8)	0.0058 (8)
C3	0.0360 (9)	0.0537 (12)	0.0555 (12)	0.0107 (9)	0.0056 (8)	0.0028 (10)
C4	0.0446 (10)	0.0589 (13)	0.0508 (11)	0.0030 (10)	0.0051 (9)	0.0147 (10)
C5	0.0481 (11)	0.0407 (10)	0.0580 (12)	0.0070 (9)	−0.0066 (9)	0.0123 (9)
C6	0.0377 (9)	0.0347 (9)	0.0479 (10)	0.0069 (7)	−0.0035 (8)	0.0002 (8)
C7	0.0473 (11)	0.0411 (11)	0.0654 (13)	0.0151 (9)	−0.0018 (9)	−0.0025 (9)
C8	0.0378 (9)	0.0475 (10)	0.0440 (10)	0.0213 (8)	0.0043 (7)	0.0045 (8)
C9	0.0433 (10)	0.0585 (12)	0.0467 (11)	0.0141 (9)	0.0101 (8)	0.0150 (9)
C10	0.0504 (11)	0.0681 (13)	0.0388 (10)	0.0217 (10)	0.0059 (8)	0.0161 (9)
C11	0.0367 (9)	0.0547 (11)	0.0432 (10)	0.0208 (8)	0.0018 (8)	0.0095 (9)
C12	0.0398 (10)	0.0536 (11)	0.0502 (11)	0.0164 (9)	0.0087 (8)	0.0152 (9)
C13	0.0483 (10)	0.0553 (12)	0.0372 (9)	0.0235 (9)	0.0085 (8)	0.0104 (9)
C14	0.0425 (10)	0.0708 (14)	0.0557 (12)	0.0215 (10)	−0.0033 (9)	0.0069 (11)
C15	0.0418 (10)	0.0607 (13)	0.0460 (11)	0.0119 (9)	0.0064 (8)	0.0086 (9)
C16	0.0497 (11)	0.0672 (14)	0.0489 (11)	0.0055 (10)	0.0019 (9)	0.0189 (10)
C17	0.0460 (10)	0.0531 (12)	0.0452 (10)	0.0136 (9)	0.0042 (8)	0.0184 (9)
C18	0.0567 (12)	0.0465 (11)	0.0566 (12)	0.0191 (10)	0.0088 (9)	0.0133 (9)
C19	0.0490 (11)	0.0500 (12)	0.0701 (13)	0.0262 (9)	0.0157 (10)	0.0202 (10)
C20	0.0368 (9)	0.0454 (11)	0.0723 (14)	0.0160 (8)	0.0088 (9)	0.0223 (10)
C21	0.0444 (11)	0.0468 (11)	0.0808 (15)	0.0199 (9)	0.0069 (10)	0.0134 (11)
C22	0.0398 (10)	0.0599 (13)	0.0672 (13)	0.0229 (9)	0.0094 (9)	0.0197 (11)
C23	0.0435 (11)	0.0531 (12)	0.0794 (15)	0.0189 (10)	0.0002 (10)	0.0158 (11)

Geometric parameters (Å, º)

S1—C15	1.805 (2)	C10—C11	1.387 (3)
S1—C14	1.810 (3)	C10—H10	0.9300
S2—C15	1.786 (2)	C11—C12	1.389 (3)
S2—C16	1.820 (2)	C11—C14	1.511 (3)
O1—C8	1.370 (2)	C12—C13	1.375 (3)
O1—C7	1.425 (2)	C12—H12	0.9300
O2—C20	1.377 (2)	C13—H13	0.9300
O2—C23	1.435 (3)	C14—H14A	0.9700
C1—C6	1.382 (3)	C14—H14B	0.9700
C1—C2	1.390 (2)	C15—H15A	0.9700
C1—H1	0.9300	C15—H15B	0.9700
C2—C3	1.393 (3)	C16—C17	1.508 (3)
C2—C23	1.495 (3)	C16—H16A	0.9700
C3—C4	1.377 (3)	C16—H16B	0.9700
C3—H3	0.9300	C17—C22	1.368 (3)
C4—C5	1.386 (3)	C17—C18	1.394 (3)
C4—H4	0.9300	C18—C19	1.382 (3)
C5—C6	1.381 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.381 (3)
C6—C7	1.509 (3)	C19—H19	0.9300
C7—H7A	0.9700	C20—C21	1.387 (3)
C7—H7B	0.9700	C21—C22	1.389 (3)
C8—C9	1.384 (3)	C21—H21	0.9300
C8—C13	1.387 (3)	C22—H22	0.9300
C9—C10	1.389 (3)	C23—H23A	0.9700
C9—H9	0.9300	C23—H23B	0.9700
C15—S1—C14	100.7 (1)	C12—C13—H13	119.8
C15—S2—C16	101.7 (1)	C8—C13—H13	119.8
C8—O1—C7	118.0 (2)	C11—C14—S1	115.7 (1)
C20—O2—C23	118.4 (2)	C11—C14—H14A	108.3
C6—C1—C2	122.1 (2)	S1—C14—H14A	108.3
C6—C1—H1	118.9	C11—C14—H14B	108.3
C2—C1—H1	118.9	S1—C14—H14B	108.3
C1—C2—C3	118.2 (2)	H14A—C14—H14B	107.4
C1—C2—C23	120.4 (2)	S2—C15—S1	111.2 (1)
C3—C2—C23	121.4 (2)	S2—C15—H15A	109.4
C4—C3—C2	120.2 (2)	S1—C15—H15A	109.4
C4—C3—H3	119.9	S2—C15—H15B	109.4
C2—C3—H3	119.9	S1—C15—H15B	109.4
C3—C4—C5	120.6 (2)	H15A—C15—H15B	108.0
C3—C4—H4	119.7	C17—C16—S2	114.2 (1)
C5—C4—H4	119.7	C17—C16—H16A	108.7
C6—C5—C4	120.4 (2)	S2—C16—H16A	108.7
C6—C5—H5	119.8	C17—C16—H16B	108.7
C4—C5—H5	119.8	S2—C16—H16B	108.7
C5—C6—C1	118.6 (2)	H16A—C16—H16B	107.6
C5—C6—C7	122.2 (2)	C22—C17—C18	117.8 (2)
C1—C6—C7	119.2 (2)	C22—C17—C16	121.5 (2)
O1—C7—C6	112.5 (2)	C18—C17—C16	120.8 (2)
O1—C7—H7A	109.1	C19—C18—C17	120.9 (2)
C6—C7—H7A	109.1	C19—C18—H18	119.5
O1—C7—H7B	109.1	C17—C18—H18	119.5
C6—C7—H7B	109.1	C18—C19—C20	120.4 (2)
H7A—C7—H7B	107.8	C18—C19—H19	119.8
O1—C8—C9	125.7 (2)	C20—C19—H19	119.8
O1—C8—C13	115.1 (2)	O2—C20—C19	115.4 (2)
C9—C8—C13	119.2 (2)	O2—C20—C21	125.4 (2)
C8—C9—C10	119.4 (2)	C19—C20—C21	119.2 (2)
C8—C9—H9	120.3	C20—C21—C22	119.3 (2)
C10—C9—H9	120.3	C20—C21—H21	120.3
C11—C10—C9	122.1 (2)	C22—C21—H21	120.3
C11—C10—H10	118.9	C17—C22—C21	122.2 (2)
C9—C10—H10	118.9	C17—C22—H22	118.9
C10—C11—C12	117.2 (2)	C21—C22—H22	118.9
C10—C11—C14	121.9 (2)	O2—C23—C2	113.9 (2)
C12—C11—C14	120.9 (2)	O2—C23—H23A	108.8
C13—C12—C11	121.6 (2)	C2—C23—H23A	108.8
C13—C12—H12	119.2	O2—C23—H23B	108.8
C11—C12—H12	119.2	C2—C23—H23B	108.8
C12—C13—C8	120.5 (2)	H23A—C23—H23B	107.7
C6—C1—C2—C3	1.7 (3)	C9—C8—C13—C12	−0.4 (3)
C6—C1—C2—C23	−177.9 (2)	C10—C11—C14—S1	128.6 (2)
C1—C2—C3—C4	0.2 (3)	C12—C11—C14—S1	−54.2 (2)
C23—C2—C3—C4	179.9 (2)	C11—C14—S1—C15	−77.0 (2)
C2—C3—C4—C5	−1.5 (3)	S1—C15—S2—C16	−76.3 (1)
C3—C4—C5—C6	0.9 (3)	S2—C15—S1—C14	171.8 (1)
C4—C5—C6—C1	1.0 (3)	C17—C16—S2—C15	−63.1 (2)
C4—C5—C6—C7	−177.8 (2)	S2—C16—C17—C22	101.7 (2)
C2—C1—C6—C5	−2.3 (3)	S2—C16—C17—C18	−78.8 (2)
C2—C1—C6—C7	176.5 (2)	C22—C17—C18—C19	2.8 (3)
C6—C7—O1—C8	−72.7 (2)	C16—C17—C18—C19	−176.8 (2)
C5—C6—C7—O1	143.5 (2)	C17—C18—C19—C20	−0.1 (3)
C1—C6—C7—O1	−35.3 (2)	C23—O2—C20—C19	−164.6 (2)
C7—O1—C8—C9	−2.7 (3)	C23—O2—C20—C21	15.2 (3)
C7—O1—C8—C13	178.0 (2)	C18—C19—C20—O2	177.0 (2)
O1—C8—C9—C10	−178.6 (2)	C18—C19—C20—C21	−2.8 (3)
C13—C8—C9—C10	0.6 (3)	O2—C20—C21—C22	−176.9 (2)
C8—C9—C10—C11	−0.4 (3)	C19—C20—C21—C22	2.9 (3)
C9—C10—C11—C12	0.0 (3)	C18—C17—C22—C21	−2.7 (3)
C9—C10—C11—C14	177.2 (2)	C16—C17—C22—C21	176.9 (2)
C10—C11—C12—C13	0.3 (3)	C20—C21—C22—C17	−0.1 (3)
C14—C11—C12—C13	−177.0 (2)	C2—C23—O2—C20	−80.5 (2)
C11—C12—C13—C8	−0.1 (3)	C1—C2—C23—O2	120.9 (2)
O1—C8—C13—C12	179.0 (2)	C3—C2—C23—O2	−58.7 (2)