(E)-3-Thia-1,5(1,3)-dibenzena­cyclo­undeca­phan-8-ene-6,11-dione 3,3-dioxide

Kotha, S.; Gupta, N.K.; Ansari, S.

doi:10.1107/S2414314620014649

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 11| November 2020| x201464

https://doi.org/10.1107/S2414314620014649

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(E)-3-Thia-1,5(1,3)-dibenzenacycloundecaphan-8-ene-6,11-dione 3,3-dioxide

Sambasivarao Kotha,^a ^* Naveen Kumar Gupta ^a ‡ and Saima Ansari ^a ‡

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India
^*Correspondence e-mail: srk@chem.iitb.ac.in

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 2 November 2020; accepted 5 November 2020; online 24 November 2020)

The molecular structure of the title cyclophane, C₂₀H₁₈O₄S, has two benzyl groups, a sulfone group, and two carbonyl groups adjacent to a double bond. The phenyl rings do not show intramolecular stacking.

Keywords: macrocycles; Grignard reaction; ring-closing metathesis; thiacyclophanes; crystal structure.

CCDC reference: 2040913

Structure description

Cyclophanes (Cram & Helgeson, 1966 ; Kotha et al., 2015 ) have become useful targets because of their unique structural features (Knobler et al., 1986 ). Their shapes are the main cause for their applications in supramolecular chemistry (Xu et al., 2008 ), material science (Yu et al., 2006 ) and medicinal chemistry (Lee et al., 2002 ). To this end, the synthesis of sulfur-containing cyclophanes (thiacyclophanes) has become of great interest for chemists (Nicolaou et al., 2010 ).

We have prepared novel thiacyclophanes using a simple strategy involving the Grignard reaction and ring-closing metathesis as key steps (Kotha et al., 2020 ). In this work, we present the single-crystal XRD study of the thiametacyclophane 1, which has two benzyl rings attached to an SO₂ moiety and a bridge at the meta positions of the phenyl rings containing two carbonyl functions connected by a double bond (Fig. 1a). The angles between the S atom, the ansa-bridging methylene C atom and pivot atom of the phenyl ring i.e. S1—C1—C2 [114.1 (3)°] and S1—C20—C18 [114.8 (3)°] are slightly widened compared with an sp³-hybridized carbon atom. The structure has completely out-of-plane phenyl groups with no intramolecular interaction between them, as is evident from the top view of the compound (Mitchell & Lai, 1984 ) (Fig. 1b).

Figure 1
The molecular structure of the title compound 1, (a) showing the atom-numbering scheme and (b) top view (H-atoms are omitted for clarity). Displacement ellipsoids are drawn at the 50% probability level.

With respect to intermolecular interactions, no π–π stacking between adjacent phenyl rings is observed, as is evident from the packing diagram shown in Fig. 2. The phenyl rings do not share any overlap. Intermolecular hydrogen bonding is also absent.

Figure 2
Crystal packing of the title compound viewed along the b axis. H atoms are omitted for clarity.

Synthesis and crystallization

For the synthesis of the compound 1, we started with the preparation of the dialdehyde 2 (Kotha et al., 2020). Later on, a Grignard reaction with 2 gave 3, which on further oxidation provided the sulfone 4. In an oven-dried, two-neck round-bottom flask, compound 4 (1eq., 50 mg) was dissolved in dry dichloromethane (20 ml). 1 Drop (0.1 eq.) of Ti(OⁱPr)₄ was added under an inert atmosphere and the reaction mixture was degassed by nitrogen gas. After degasification, Grubbs' second generation catalyst (5–10 mmol-%) was added, and the reaction mixture was refluxed. After completion of the reaction (TLC monitoring), the crude product was then subjected to oxidation by using pyridinium chlorochromate (2.5 eq.) at room temperature. After completion of the reaction (TLC monitoring), the product was concentrated and purified by silica gel column chromatography using petroleum ether and ethyl acetate as the eluent to afford the desired compound 1 (Fig. 3). The single crystals were obtained by recrystallization in ethyl acetate and petroleum ether (1:2).

Figure 3
Synthesis of thiametacyclophane 1.

Yield 27 mg, 58%, m.p. 186–188°C, appearance: colourless solid, R_f = 0.5 (50% EtOAc–petroleum ether), ¹H NMR 400 MHz, CDCl₃) δ 8.04 (d, J = 8.0 Hz, 2H), 7.91 (d, J = 8.0 Hz, 2H), 7.56–7.51 (m, 4H), 5.83 (t, J = 3.2 Hz, 2H), 4.08 (s, 4H), 3.59 (m, 4H) p.p.m., ¹³C NMR (100 MHz, CDCl₃) δ 197.1, 136.9, 135.4, 131.2, 130.1, 129.4, 128.7, 127.8, 57.1, 43.7 p.p.m., HRMS (ESI) m/z calculated C₂₀H₁₈O₄SK[M + K]⁺ 393.0557, found 393.0551.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₄S
M_r	354.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	8.4257 (11), 9.0522 (9), 22.237 (2)
β (°)	98.303 (12)
V (Å³)	1678.3 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.22
Crystal size (mm)	0.15 × 0.09 × 0.03

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku, 2018 )
T_min, T_max	0.921, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6670, 2942, 1671
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.165, 1.04
No. of reflections	2942
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.42
Computer programs: CrysAlis PRO (Rigaku, 2018), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2040913

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314620014649/bt4102sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620014649/bt4102Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku, 2018); cell refinement: CrysAlis PRO (Rigaku, 2018); data reduction: CrysAlis PRO (Rigaku, 2018); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(E)-3-Thia-1,5(1,3)-dibenzenacycloundecaphan-8-ene-6,11-dione 3,3-dioxide top

Crystal data top

C₂₀H₁₈O₄S	F(000) = 744
M_r = 354.40	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4257 (11) Å	Cell parameters from 1833 reflections
b = 9.0522 (9) Å	θ = 2.4–26.4°
c = 22.237 (2) Å	µ = 0.22 mm⁻¹
β = 98.303 (12)°	T = 150 K
V = 1678.3 (3) Å³	Block, colourless
Z = 4	0.14 × 0.09 × 0.03 mm

Data collection top

Rigaku Saturn724+ diffractometer	2942 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1671 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlisPro; Rigaku, 2018)	k = −7→10
T_min = 0.921, T_max = 1.000	l = −18→26
6670 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.069	H-atom parameters constrained
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.0393P)² + 0.7221P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2942 reflections	Δρ_max = 0.42 e Å⁻³
226 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. H atoms were refined using a riding model with U(H)=1.2UeqC and with Caromatic—H = 0.95?Å or Cmethylene—H = 0.99?Å.

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

	x	y	z	U_iso*/U_eq
S1	0.78574 (15)	0.72123 (11)	0.70216 (5)	0.0316 (4)
O2	0.7211 (4)	0.8626 (3)	0.68124 (14)	0.0421 (9)
O1	0.8964 (4)	0.7170 (3)	0.75787 (13)	0.0392 (9)
O3	0.1830 (4)	0.3005 (3)	0.50373 (14)	0.0475 (10)
O4	1.0566 (4)	−0.0096 (3)	0.62633 (17)	0.0515 (10)
C6	1.0134 (5)	0.2434 (4)	0.64281 (18)	0.0267 (10)
C14	0.3355 (6)	0.4516 (4)	0.57729 (19)	0.0305 (11)
C1	0.8785 (5)	0.6454 (4)	0.64184 (18)	0.0267 (11)
H1A	0.7948	0.6265	0.6067	0.032*
H1B	0.9536	0.7194	0.6291	0.032*
C8	0.9719 (6)	0.0980 (4)	0.6111 (2)	0.0325 (11)
C7	0.9243 (5)	0.3719 (4)	0.62869 (18)	0.0249 (10)
H7	0.8320	0.3692	0.5986	0.030*
C15	0.2412 (5)	0.5744 (5)	0.5605 (2)	0.0323 (11)
H15	0.1555	0.5682	0.5278	0.039*
C2	0.9693 (5)	0.5035 (4)	0.65816 (18)	0.0250 (10)
C19	0.4621 (5)	0.4625 (4)	0.62534 (18)	0.0267 (10)
H19	0.5263	0.3782	0.6372	0.032*
C4	1.1943 (5)	0.3788 (5)	0.7164 (2)	0.0347 (12)
H4	1.2863	0.3821	0.7466	0.042*
C13	0.2932 (6)	0.3062 (5)	0.5460 (2)	0.0352 (12)
C3	1.1054 (5)	0.5051 (5)	0.7015 (2)	0.0315 (11)
H3	1.1382	0.5952	0.7215	0.038*
C9	0.8348 (5)	0.0863 (5)	0.5607 (2)	0.0357 (12)
H9A	0.8362	−0.0127	0.5419	0.043*
H9B	0.8486	0.1605	0.5291	0.043*
C11	0.5455 (5)	0.1580 (4)	0.5472 (2)	0.0329 (11)
H11	0.5545	0.1882	0.5069	0.040*
C5	1.1485 (5)	0.2470 (4)	0.68701 (18)	0.0302 (11)
H5	1.2091	0.1596	0.6970	0.036*
C17	0.3971 (6)	0.7161 (4)	0.63881 (19)	0.0319 (11)
H17	0.4166	0.8070	0.6600	0.038*
C16	0.2725 (5)	0.7065 (5)	0.59171 (19)	0.0337 (12)
H16	0.2076	0.7906	0.5804	0.040*
C12	0.3844 (6)	0.1679 (4)	0.5677 (2)	0.0349 (12)
H12A	0.3985	0.1652	0.6127	0.042*
H12B	0.3200	0.0805	0.5525	0.042*
C18	0.4949 (5)	0.5959 (4)	0.65603 (19)	0.0271 (10)
C10	0.6757 (6)	0.1099 (4)	0.5816 (2)	0.0339 (12)
H10	0.6680	0.0885	0.6229	0.041*
C20	0.6247 (5)	0.6022 (4)	0.71042 (19)	0.0293 (11)
H20A	0.6675	0.5013	0.7188	0.035*
H20B	0.5760	0.6343	0.7462	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0419 (8)	0.0204 (6)	0.0310 (6)	−0.0001 (5)	0.0005 (6)	−0.0055 (5)
O2	0.054 (2)	0.0163 (14)	0.053 (2)	0.0032 (15)	−0.0005 (18)	−0.0051 (14)
O1	0.045 (2)	0.0354 (17)	0.0338 (18)	0.0011 (15)	−0.0077 (16)	−0.0115 (14)
O3	0.046 (2)	0.053 (2)	0.038 (2)	0.0074 (17)	−0.0131 (18)	−0.0068 (16)
O4	0.038 (2)	0.0275 (17)	0.085 (3)	0.0069 (16)	−0.002 (2)	−0.0016 (17)
C6	0.030 (3)	0.026 (2)	0.025 (2)	0.000 (2)	0.006 (2)	0.0027 (18)
C14	0.033 (3)	0.030 (2)	0.028 (3)	0.002 (2)	0.003 (2)	0.0018 (19)
C1	0.037 (3)	0.019 (2)	0.023 (2)	−0.003 (2)	0.002 (2)	−0.0017 (18)
C8	0.037 (3)	0.026 (2)	0.035 (3)	−0.001 (2)	0.008 (2)	−0.003 (2)
C7	0.024 (3)	0.027 (2)	0.023 (2)	0.001 (2)	0.000 (2)	0.0004 (18)
C15	0.030 (3)	0.041 (3)	0.027 (3)	0.007 (2)	0.005 (2)	0.009 (2)
C2	0.032 (3)	0.023 (2)	0.021 (2)	−0.003 (2)	0.005 (2)	0.0038 (18)
C19	0.027 (3)	0.024 (2)	0.030 (2)	0.007 (2)	0.009 (2)	0.0038 (18)
C4	0.026 (3)	0.046 (3)	0.030 (3)	−0.005 (2)	−0.001 (2)	−0.001 (2)
C13	0.036 (3)	0.044 (3)	0.026 (2)	0.006 (2)	0.003 (2)	−0.001 (2)
C3	0.032 (3)	0.028 (2)	0.034 (3)	0.000 (2)	0.004 (2)	−0.0016 (19)
C9	0.037 (3)	0.029 (2)	0.040 (3)	0.006 (2)	0.001 (2)	−0.007 (2)
C11	0.037 (3)	0.025 (2)	0.036 (3)	0.000 (2)	0.001 (2)	−0.008 (2)
C5	0.030 (3)	0.031 (2)	0.030 (2)	−0.002 (2)	0.004 (2)	0.005 (2)
C17	0.038 (3)	0.027 (2)	0.032 (3)	0.009 (2)	0.010 (2)	0.003 (2)
C16	0.036 (3)	0.031 (2)	0.034 (3)	0.012 (2)	0.004 (2)	0.014 (2)
C12	0.043 (3)	0.029 (2)	0.032 (3)	−0.005 (2)	0.001 (2)	−0.003 (2)
C18	0.028 (3)	0.027 (2)	0.028 (2)	−0.001 (2)	0.009 (2)	0.0023 (19)
C10	0.039 (3)	0.027 (2)	0.031 (3)	0.002 (2)	−0.006 (2)	−0.0037 (19)
C20	0.038 (3)	0.025 (2)	0.026 (2)	0.001 (2)	0.007 (2)	0.0033 (18)

Geometric parameters (Å, º) top

S1—O2	1.441 (3)	C4—H4	0.9500
S1—O1	1.439 (3)	C4—C3	1.380 (6)
S1—C1	1.785 (4)	C4—C5	1.388 (5)
S1—C20	1.763 (4)	C13—C12	1.511 (6)
O3—C13	1.223 (5)	C3—H3	0.9500
O4—C8	1.226 (5)	C9—H9A	0.9900
C6—C8	1.510 (5)	C9—H9B	0.9900
C6—C7	1.395 (5)	C9—C10	1.497 (6)
C6—C5	1.393 (5)	C11—H11	0.9500
C14—C15	1.386 (6)	C11—C12	1.496 (6)
C14—C19	1.400 (5)	C11—C10	1.318 (5)
C14—C13	1.507 (6)	C5—H5	0.9500
C1—H1A	0.9900	C17—H17	0.9500
C1—H1B	0.9900	C17—C16	1.375 (6)
C1—C2	1.512 (5)	C17—C18	1.385 (5)
C8—C9	1.492 (6)	C16—H16	0.9500
C7—H7	0.9500	C12—H12A	0.9900
C7—C2	1.385 (5)	C12—H12B	0.9900
C15—H15	0.9500	C18—C20	1.510 (6)
C15—C16	1.389 (6)	C10—H10	0.9500
C2—C3	1.388 (6)	C20—H20A	0.9900
C19—H19	0.9500	C20—H20B	0.9900
C19—C18	1.395 (5)

O2—S1—C1	106.56 (19)	C2—C3—H3	119.2
O2—S1—C20	108.4 (2)	C4—C3—C2	121.5 (4)
O1—S1—O2	117.98 (18)	C4—C3—H3	119.2
O1—S1—C1	109.7 (2)	C8—C9—H9A	109.0
O1—S1—C20	107.84 (19)	C8—C9—H9B	109.0
C20—S1—C1	105.7 (2)	C8—C9—C10	112.8 (4)
C7—C6—C8	122.7 (4)	H9A—C9—H9B	107.8
C5—C6—C8	117.4 (4)	C10—C9—H9A	109.0
C5—C6—C7	119.8 (4)	C10—C9—H9B	109.0
C15—C14—C19	119.5 (4)	C12—C11—H11	118.0
C15—C14—C13	119.2 (4)	C10—C11—H11	118.0
C19—C14—C13	121.2 (4)	C10—C11—C12	123.9 (4)
S1—C1—H1A	108.7	C6—C5—H5	120.2
S1—C1—H1B	108.7	C4—C5—C6	119.7 (4)
H1A—C1—H1B	107.6	C4—C5—H5	120.2
C2—C1—S1	114.1 (3)	C16—C17—H17	119.4
C2—C1—H1A	108.7	C16—C17—C18	121.3 (4)
C2—C1—H1B	108.7	C18—C17—H17	119.4
O4—C8—C6	118.5 (4)	C15—C16—H16	119.9
O4—C8—C9	120.5 (4)	C17—C16—C15	120.3 (4)
C9—C8—C6	121.0 (4)	C17—C16—H16	119.9
C6—C7—H7	119.7	C13—C12—H12A	108.9
C2—C7—C6	120.6 (4)	C13—C12—H12B	108.9
C2—C7—H7	119.7	C11—C12—C13	113.2 (4)
C14—C15—H15	120.1	C11—C12—H12A	108.9
C14—C15—C16	119.8 (4)	C11—C12—H12B	108.9
C16—C15—H15	120.1	H12A—C12—H12B	107.8
C7—C2—C1	121.5 (4)	C19—C18—C20	119.6 (4)
C7—C2—C3	118.7 (4)	C17—C18—C19	118.5 (4)
C3—C2—C1	119.8 (3)	C17—C18—C20	121.7 (4)
C14—C19—H19	119.7	C9—C10—H10	117.5
C18—C19—C14	120.6 (4)	C11—C10—C9	125.0 (4)
C18—C19—H19	119.7	C11—C10—H10	117.5
C3—C4—H4	120.2	S1—C20—H20A	108.6
C3—C4—C5	119.7 (4)	S1—C20—H20B	108.6
C5—C4—H4	120.2	C18—C20—S1	114.8 (3)
O3—C13—C14	119.6 (4)	C18—C20—H20A	108.6
O3—C13—C12	120.3 (4)	C18—C20—H20B	108.6
C14—C13—C12	120.0 (4)	H20A—C20—H20B	107.6

S1—C1—C2—C7	117.0 (4)	C7—C2—C3—C4	−1.1 (7)
S1—C1—C2—C3	−66.1 (5)	C15—C14—C19—C18	−0.6 (7)
O2—S1—C1—C2	173.6 (3)	C15—C14—C13—O3	4.7 (7)
O2—S1—C20—C18	50.0 (3)	C15—C14—C13—C12	−174.0 (4)
O1—S1—C1—C2	44.9 (4)	C19—C14—C15—C16	−0.4 (7)
O1—S1—C20—C18	178.8 (3)	C19—C14—C13—O3	−179.2 (4)
O3—C13—C12—C11	103.5 (5)	C19—C14—C13—C12	2.1 (7)
O4—C8—C9—C10	115.5 (5)	C19—C18—C20—S1	118.1 (4)
C6—C8—C9—C10	−66.8 (5)	C13—C14—C15—C16	175.8 (4)
C6—C7—C2—C1	177.5 (4)	C13—C14—C19—C18	−176.7 (4)
C6—C7—C2—C3	0.6 (6)	C3—C4—C5—C6	0.0 (7)
C14—C15—C16—C17	0.4 (7)	C5—C6—C8—O4	1.3 (6)
C14—C19—C18—C17	1.5 (6)	C5—C6—C8—C9	−176.4 (4)
C14—C19—C18—C20	175.8 (4)	C5—C6—C7—C2	0.2 (6)
C14—C13—C12—C11	−77.8 (5)	C5—C4—C3—C2	0.8 (7)
C1—S1—C20—C18	−63.9 (3)	C17—C18—C20—S1	−67.7 (5)
C1—C2—C3—C4	−178.1 (4)	C16—C17—C18—C19	−1.5 (7)
C8—C6—C7—C2	−178.5 (4)	C16—C17—C18—C20	−175.7 (4)
C8—C6—C5—C4	178.3 (4)	C12—C11—C10—C9	174.3 (4)
C8—C9—C10—C11	154.2 (4)	C18—C17—C16—C15	0.5 (7)
C7—C6—C8—O4	−180.0 (4)	C10—C11—C12—C13	139.7 (4)
C7—C6—C8—C9	2.3 (7)	C20—S1—C1—C2	−71.2 (3)
C7—C6—C5—C4	−0.5 (6)

Footnotes

‡NKG and SA contributed equally.

Acknowledgements

We thank Mr Darshan S Mhatre for his help in collecting the X-ray data and with the structure refinement.

Funding information

Funding for this research was provided by: Department of Science and Technology, Ministry of Science and Technology, India (award No. SR/S2/JCB-33/2010 to Sambasivarao Kotha); Council of Scientific and Industrial Research, India (scholarship to Naveen Kumar Gupta); University Grants Commission (scholarship to Saima Ansari).

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