Crystal structure of tetra­ethyl 27,30-dioxo-7,12,20,25-tetra-tert-but­yl-3,16-dioxa-9,22,28,31-tetra­thia­hepta­cyclo­[21.3.1.11,5.14,8.110,14.114,18.117,21]dotriaconta-4,6,8(29),10,12,17,19,21(32),23,25-deca­ene-2,2,15,15-tetra­carboxyl­ate

Akkurt, M.; Jasinski, J.P.; Mohamed, S.K.; Omran, O.A.; Albayati, M.R.

doi:10.1107/S205698901501748X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o778-o779

doi:10.1107/S205698901501748X

Open

access

Crystal structure of tetraethyl 27,30-dioxo-7,12,20,25-tetra-tert-butyl-3,16-dioxa-9,22,28,31-tetrathiaheptacyclo[21.3.1.1^1,5.1^4,8.1^10,14.1^14,18.1^17,21]dotriaconta-4,6,8(29),10,12,17,19,21(32),23,25-decaene-2,2,15,15-tetracarboxylate

Mehmet Akkurt,^a Jerry P. Jasinski,^b Shaaban K. Mohamed,^c,^d Omran A. Omran ^e,^f and Mustafa R. Albayati ^g ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^eMedical Laboratory Department, College of Science, Majmaah University, 11932, Saudi Arabia, ^fChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^gKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Ishida, Okayama University, Japan (Received 16 September 2015; accepted 18 September 2015; online 26 September 2015)

The asymmetric unit of the title compound, C₅₄H₆₄O₁₂S₄, consists of one half of the molecule, which is located on an inversion centre. The heterocyclic six-membered ring adopts a distorted envelope conformation with the spiro C atom as the flap. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds with an R²₂(14) motif, forming a chain along the b-axis direction.

Keywords: crystal structure; calixarenes; macrocycles; hydrogen bonding.

CCDC reference: 1425819

1. Related literature

For industrial application of calixarenes, see: Shokova & Kovalev (2003 ); Stoikov et al. (2003 ). For macrocyclic reactions of calixarenes, see: Agrawal & Pancholi (2007 ); Higuchi et al. (2000 ); Omran & Antipin (2014 ).

2. Experimental

2.1. Crystal data

C₅₄H₆₄O₁₂S₄
M_r = 1033.29
Triclinic, $[P \overline 1]$
a = 10.9366 (6) Å
b = 11.7386 (5) Å
c = 12.6262 (8) Å
α = 100.018 (4)°
β = 113.884 (6)°
γ = 105.884 (4)°
V = 1348.75 (16) Å³
Z = 1
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.49 × 0.32 × 0.14 mm

2.2. Data collection

Agilent Xcalibur, Eos, Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ) T_min = 0.715, T_max = 0.967
16365 measured reflections
8908 independent reflections
6481 reflections with I > 2σ(I)
R_int = 0.036

2.3. Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.169
S = 1.07
8908 reflections
324 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26A⋯O4ⁱ	0.97	2.35	3.298 (5)	164
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1425819

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901501748X/is5424sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901501748X/is5424Isup2.hkl

checkCIF report

Comment top

The macrocyclic calixarenes have been considered to be not only as good substrats in industrial chemistry but also in research field of supramolecular chemistry (Agrawal & Pancholi, 2007; Higuchi et al., 2000; Omran & Antipin, 2014). They have also been used as sensors, catalysis and molecular recognition or ion separtion (Shokova & Kovalev, 2003; Stoikov et al., 2003). In this context and following to our on-going study we report in this study the synthesis and crystal structure of the title compound.

Figure 1 shows the title molecule which lies on a crystallographic inversion centre. The heterocyclic six-membered ring (S1/C2/C21/O2/C13/C14) adopts a distorted envelope conformation with the puckering parameters of Q_T = 0.547 (2) Å, θ = 50.6 (2)° and φ = 65.2 (3)°. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules, forming fourteen-membered rings with R₂²(14) ring motifs, into chains along the b axis (Fig. 2).

Related literature top

For industrial application of calixarenes, see: Shokova & Kovalev (2003); Stoikov et al. (2003). For macrocyclic reactions of calixarenes, see: Agrawal & Pancholi (2007); Higuchi et al. (2000); Omran & Antipin (2014).

Experimental top

A mixture of 1.5 g (2.08 mmol) thiacalexarene (TCA), 10 g sodium carbonate, 0.5 g of tetraethylammonium bromide (TEAB) and diethyl bromomalonate 3 ml (8. 02 mmol) in 50 ml benzene was heated at 373 K with stirring for 6 days. The reaction mixture was filtered off and the benzene layer was evaporated under vacuum to dryness. The solid residue was washed by hydrochloric diluted solution and extracted by methylene chloride (3 times). The methylene chloride portions were concentrated and methanol was added. Yellow color of two solid mixture products were precipitated and filtered off. The mixture was separated by fractional crystallization by using a mixture of methylene chloride / methanol (1:1 v:v) to afford the title compound as yellow crystals in 85% yield.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity. [Symmetry code: (a) 1 - x, 1 - y, 1 - z.]
	Fig. 2. The molecular packing of the title compound viewed down the a axis. H atoms not involved in the C—H···O hydrogen bonds are omitted for clarity.

Tetraethyl 27,30-dioxo-7,12,20,25-tetra-tert-butyl-3,16-dioxa-9,22,28,31-tetrathiaheptacyclo[21.3.1.1^1,5.1^4,8.1^10,14.1^14,18.1^17,21]dotriaconta-4,6,8(29),10,12,17,19,21 (32),23,25-decaene-2,2,15,15-tetracarboxylate top

Crystal data top

C₅₄H₆₄O₁₂S₄	Z = 1
M_r = 1033.29	F(000) = 548
Triclinic, P1	D_x = 1.272 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9366 (6) Å	Cell parameters from 4552 reflections
b = 11.7386 (5) Å	θ = 3.6–32.8°
c = 12.6262 (8) Å	µ = 0.24 mm⁻¹
α = 100.018 (4)°	T = 293 K
β = 113.884 (6)°	Prism, yellow
γ = 105.884 (4)°	0.49 × 0.32 × 0.14 mm
V = 1348.75 (16) Å³

Data collection top

Agilent Xcalibur, Eos, Gemini diffractometer	8908 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6481 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 16.0416 pixels mm^-1	θ_max = 32.8°, θ_min = 3.3°
ω scans	h = −14→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −16→17
T_min = 0.715, T_max = 0.967	l = −18→17
16365 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.0595P)² + 1.2423P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
8908 reflections	Δρ_max = 0.58 e Å⁻³
324 parameters	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₅₄H₆₄O₁₂S₄	γ = 105.884 (4)°
M_r = 1033.29	V = 1348.75 (16) Å³
Triclinic, P1	Z = 1
a = 10.9366 (6) Å	Mo Kα radiation
b = 11.7386 (5) Å	µ = 0.24 mm⁻¹
c = 12.6262 (8) Å	T = 293 K
α = 100.018 (4)°	0.49 × 0.32 × 0.14 mm
β = 113.884 (6)°

Data collection top

Agilent Xcalibur, Eos, Gemini diffractometer	8908 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	6481 reflections with I > 2σ(I)
T_min = 0.715, T_max = 0.967	R_int = 0.036
16365 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.07	Δρ_max = 0.58 e Å⁻³
8908 reflections	Δρ_min = −0.38 e Å⁻³
324 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	0.38215 (6)	0.57806 (5)	0.18169 (5)	0.0238 (2)
S2	0.76046 (6)	0.40179 (5)	0.44376 (5)	0.0202 (1)
O1	0.49791 (19)	0.46545 (16)	0.38746 (17)	0.0296 (5)
O2	0.42622 (17)	0.67374 (14)	0.44663 (14)	0.0215 (4)
O3	0.7778 (2)	0.76578 (19)	0.56813 (17)	0.0372 (6)
O4	0.6528 (2)	0.86471 (17)	0.62364 (16)	0.0335 (5)
O5	0.3815 (2)	0.84596 (18)	0.33706 (19)	0.0389 (6)
O6	0.6192 (2)	0.93356 (16)	0.39687 (19)	0.0357 (6)
C1	0.6629 (3)	0.7156 (2)	0.2902 (2)	0.0234 (6)
C2	0.5554 (2)	0.64613 (19)	0.32531 (19)	0.0207 (6)
C3	0.5857 (2)	0.53717 (19)	0.37028 (19)	0.0207 (6)
C4	0.7215 (2)	0.52250 (18)	0.38669 (18)	0.0181 (5)
C5	0.8098 (2)	0.59444 (19)	0.35403 (19)	0.0212 (6)
C6	0.7789 (2)	0.69103 (19)	0.30120 (19)	0.0208 (6)
C7	0.8882 (3)	0.7654 (2)	0.2675 (3)	0.0311 (7)
C8	0.9031 (5)	0.6736 (3)	0.1744 (4)	0.0612 (16)
C9	0.8420 (4)	0.8595 (3)	0.2101 (4)	0.0574 (14)
C10	1.0347 (4)	0.8317 (3)	0.3815 (4)	0.0619 (13)
C11	0.9349 (2)	0.56128 (19)	0.68011 (19)	0.0211 (6)
C12	0.8017 (2)	0.46496 (19)	0.59880 (18)	0.0188 (5)
C13	0.2968 (2)	0.58308 (18)	0.35982 (18)	0.0183 (5)
C14	0.2600 (2)	0.53000 (19)	0.23855 (19)	0.0198 (5)
C15	0.8742 (2)	0.5656 (2)	0.84102 (19)	0.0227 (6)
C16	0.9745 (2)	0.61370 (19)	0.8030 (2)	0.0215 (6)
C17	1.1205 (3)	0.7230 (2)	0.8879 (2)	0.0267 (6)
C18	1.1203 (3)	0.8358 (3)	0.8437 (3)	0.0508 (10)
C19	1.2448 (3)	0.6880 (3)	0.8872 (3)	0.0381 (8)
C20	1.1473 (3)	0.7592 (3)	1.0203 (3)	0.0459 (9)
C21	0.5354 (2)	0.73515 (19)	0.41950 (19)	0.0206 (6)
C22	0.6726 (2)	0.7896 (2)	0.5459 (2)	0.0230 (6)
C23	0.7668 (3)	0.9188 (3)	0.7497 (2)	0.0388 (8)
C24	0.7386 (4)	0.8350 (4)	0.8208 (3)	0.0584 (11)
C25	0.4997 (3)	0.8438 (2)	0.3777 (2)	0.0254 (6)
C26	0.6045 (4)	1.0460 (2)	0.3669 (3)	0.0421 (9)
C27	0.5772 (5)	1.0344 (4)	0.2411 (4)	0.0649 (16)
H1	0.64760	0.77950	0.25890	0.0280*
H5	0.89410	0.58210	0.36560	0.0250*
H8A	0.97220	0.71940	0.15320	0.0920*
H8B	0.81100	0.62980	0.10200	0.0920*
H8C	0.93540	0.61450	0.20990	0.0920*
H9A	0.83400	0.91880	0.26720	0.0860*
H9B	0.74990	0.81680	0.13740	0.0860*
H9C	0.91270	0.90270	0.18920	0.0860*
H10A	1.10450	0.87590	0.36030	0.0930*
H10B	1.06450	0.77120	0.41620	0.0930*
H10C	1.02770	0.89000	0.44030	0.0930*
H11	0.99940	0.59170	0.65170	0.0250*
H15	0.89760	0.59850	0.92240	0.0270*
H18A	1.04430	0.85990	0.84670	0.0760*
H18B	1.10450	0.81440	0.76110	0.0760*
H18C	1.21180	0.90420	0.89550	0.0760*
H19A	1.23340	0.66930	0.80590	0.0570*
H19B	1.24400	0.61590	0.91340	0.0570*
H19C	1.33510	0.75680	0.94200	0.0570*
H20A	1.13890	0.68680	1.04660	0.0690*
H20B	1.07720	0.79130	1.02490	0.0690*
H20C	1.24280	0.82220	1.07240	0.0690*
H23A	0.77040	1.00060	0.78550	0.0460*
H23B	0.85940	0.92930	0.75290	0.0460*
H24A	0.81310	0.87190	0.90470	0.0870*
H24B	0.73800	0.75500	0.78670	0.0870*
H24C	0.64640	0.82430	0.81680	0.0870*
H26A	0.52530	1.05910	0.37660	0.0510*
H26B	0.69250	1.11830	0.42330	0.0510*
H27A	0.56900	1.10930	0.22420	0.0980*
H27B	0.48880	0.96410	0.18510	0.0980*
H27C	0.65590	1.02200	0.23160	0.0980*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0226 (3)	0.0322 (3)	0.0206 (2)	0.0101 (2)	0.0132 (2)	0.0111 (2)
S2	0.0258 (3)	0.0211 (2)	0.0220 (2)	0.0135 (2)	0.0152 (2)	0.0090 (2)
O1	0.0275 (9)	0.0328 (8)	0.0439 (10)	0.0162 (7)	0.0236 (8)	0.0235 (7)
O2	0.0186 (7)	0.0234 (7)	0.0220 (7)	0.0053 (6)	0.0113 (6)	0.0066 (6)
O3	0.0275 (9)	0.0493 (11)	0.0312 (9)	0.0218 (8)	0.0096 (8)	0.0042 (8)
O4	0.0275 (9)	0.0360 (9)	0.0298 (9)	0.0157 (7)	0.0094 (7)	−0.0006 (7)
O5	0.0309 (10)	0.0413 (10)	0.0516 (12)	0.0237 (8)	0.0174 (9)	0.0208 (9)
O6	0.0345 (10)	0.0260 (8)	0.0558 (12)	0.0153 (7)	0.0238 (9)	0.0225 (8)
C1	0.0257 (11)	0.0233 (10)	0.0301 (11)	0.0105 (8)	0.0183 (9)	0.0143 (8)
C2	0.0197 (10)	0.0225 (9)	0.0244 (10)	0.0099 (8)	0.0123 (8)	0.0106 (8)
C3	0.0223 (10)	0.0222 (9)	0.0248 (10)	0.0113 (8)	0.0146 (8)	0.0113 (8)
C4	0.0204 (9)	0.0182 (8)	0.0208 (9)	0.0092 (7)	0.0130 (8)	0.0072 (7)
C5	0.0213 (10)	0.0233 (9)	0.0254 (10)	0.0104 (8)	0.0151 (8)	0.0092 (8)
C6	0.0219 (10)	0.0208 (9)	0.0235 (10)	0.0067 (7)	0.0146 (8)	0.0088 (7)
C7	0.0292 (12)	0.0331 (12)	0.0461 (14)	0.0133 (10)	0.0268 (11)	0.0227 (11)
C8	0.087 (3)	0.065 (2)	0.083 (3)	0.038 (2)	0.074 (2)	0.0424 (19)
C9	0.0498 (19)	0.066 (2)	0.099 (3)	0.0315 (16)	0.053 (2)	0.064 (2)
C10	0.0328 (17)	0.056 (2)	0.080 (3)	−0.0015 (14)	0.0203 (17)	0.0304 (18)
C11	0.0205 (10)	0.0255 (10)	0.0250 (10)	0.0122 (8)	0.0141 (8)	0.0119 (8)
C12	0.0199 (9)	0.0231 (9)	0.0188 (9)	0.0120 (7)	0.0103 (8)	0.0104 (7)
C13	0.0182 (9)	0.0205 (9)	0.0206 (9)	0.0104 (7)	0.0103 (8)	0.0092 (7)
C14	0.0189 (10)	0.0249 (9)	0.0210 (9)	0.0106 (8)	0.0117 (8)	0.0106 (7)
C15	0.0227 (10)	0.0277 (10)	0.0199 (9)	0.0118 (8)	0.0105 (8)	0.0084 (8)
C16	0.0191 (10)	0.0221 (9)	0.0241 (10)	0.0091 (8)	0.0101 (8)	0.0076 (8)
C17	0.0194 (10)	0.0289 (11)	0.0273 (11)	0.0068 (8)	0.0102 (9)	0.0051 (8)
C18	0.0352 (16)	0.0312 (13)	0.069 (2)	0.0051 (11)	0.0135 (15)	0.0188 (14)
C19	0.0202 (12)	0.0452 (15)	0.0366 (14)	0.0085 (10)	0.0095 (10)	0.0018 (11)
C20	0.0297 (14)	0.0549 (18)	0.0319 (14)	0.0008 (12)	0.0132 (12)	−0.0052 (12)
C21	0.0189 (10)	0.0215 (9)	0.0245 (10)	0.0092 (7)	0.0111 (8)	0.0100 (8)
C22	0.0228 (10)	0.0218 (9)	0.0261 (10)	0.0098 (8)	0.0117 (9)	0.0094 (8)
C23	0.0336 (14)	0.0396 (14)	0.0291 (12)	0.0133 (11)	0.0083 (11)	−0.0026 (10)
C24	0.061 (2)	0.072 (2)	0.0471 (19)	0.0313 (19)	0.0247 (17)	0.0234 (17)
C25	0.0264 (11)	0.0260 (10)	0.0295 (11)	0.0143 (9)	0.0149 (9)	0.0109 (8)
C26	0.0486 (17)	0.0243 (11)	0.0596 (18)	0.0177 (11)	0.0259 (15)	0.0214 (12)
C27	0.090 (3)	0.064 (2)	0.085 (3)	0.046 (2)	0.060 (3)	0.052 (2)

Geometric parameters (Å, º) top

S1—C2	1.844 (2)	C21—C25	1.548 (3)
S1—C14	1.767 (2)	C23—C24	1.495 (5)
S2—C4	1.774 (2)	C26—C27	1.466 (6)
S2—C12	1.784 (2)	C1—H1	0.9300
O1—C3	1.211 (3)	C5—H5	0.9300
O2—C13	1.360 (3)	C8—H8A	0.9600
O2—C21	1.417 (3)	C8—H8B	0.9600
O3—C22	1.193 (3)	C8—H8C	0.9600
O4—C22	1.328 (3)	C9—H9A	0.9600
O4—C23	1.449 (3)	C9—H9B	0.9600
O5—C25	1.192 (4)	C9—H9C	0.9600
O6—C25	1.334 (4)	C10—H10A	0.9600
O6—C26	1.467 (3)	C10—H10B	0.9600
C1—C2	1.506 (4)	C10—H10C	0.9600
C1—C6	1.336 (4)	C11—H11	0.9300
C2—C3	1.549 (3)	C15—H15	0.9300
C2—C21	1.568 (3)	C18—H18A	0.9600
C3—C4	1.477 (3)	C18—H18B	0.9600
C4—C5	1.347 (3)	C18—H18C	0.9600
C5—C6	1.461 (3)	C19—H19A	0.9600
C6—C7	1.530 (4)	C19—H19B	0.9600
C7—C8	1.543 (6)	C19—H19C	0.9600
C7—C9	1.513 (5)	C20—H20A	0.9600
C7—C10	1.518 (6)	C20—H20B	0.9600
C11—C12	1.392 (3)	C20—H20C	0.9600
C11—C16	1.397 (3)	C23—H23A	0.9700
C12—C13ⁱ	1.406 (3)	C23—H23B	0.9700
C13—C14	1.388 (3)	C24—H24A	0.9600
C14—C15ⁱ	1.391 (3)	C24—H24B	0.9600
C15—C16	1.391 (3)	C24—H24C	0.9600
C16—C17	1.536 (4)	C26—H26A	0.9700
C17—C18	1.524 (4)	C26—H26B	0.9700
C17—C19	1.527 (5)	C27—H27A	0.9600
C17—C20	1.533 (4)	C27—H27B	0.9600
C21—C22	1.545 (3)	C27—H27C	0.9600

C2—S1—C14	100.38 (10)	C4—C5—H5	119.00
C4—S2—C12	100.21 (10)	C6—C5—H5	119.00
C13—O2—C21	122.89 (17)	C7—C8—H8A	109.00
C22—O4—C23	117.2 (2)	C7—C8—H8B	110.00
C25—O6—C26	117.2 (3)	C7—C8—H8C	109.00
C2—C1—C6	124.0 (2)	H8A—C8—H8B	109.00
S1—C2—C1	104.10 (15)	H8A—C8—H8C	109.00
S1—C2—C3	107.77 (15)	H8B—C8—H8C	109.00
S1—C2—C21	106.81 (16)	C7—C9—H9A	109.00
C1—C2—C3	114.2 (2)	C7—C9—H9B	110.00
C1—C2—C21	112.76 (19)	C7—C9—H9C	109.00
C3—C2—C21	110.56 (17)	H9A—C9—H9B	109.00
O1—C3—C2	120.2 (2)	H9A—C9—H9C	109.00
O1—C3—C4	122.2 (2)	H9B—C9—H9C	109.00
C2—C3—C4	117.6 (2)	C7—C10—H10A	110.00
S2—C4—C3	117.90 (16)	C7—C10—H10B	109.00
S2—C4—C5	120.84 (19)	C7—C10—H10C	109.00
C3—C4—C5	121.2 (2)	H10A—C10—H10B	110.00
C4—C5—C6	122.9 (2)	H10A—C10—H10C	109.00
C1—C6—C5	119.7 (2)	H10B—C10—H10C	109.00
C1—C6—C7	122.8 (2)	C12—C11—H11	119.00
C5—C6—C7	117.4 (2)	C16—C11—H11	119.00
C6—C7—C8	108.9 (2)	C16—C15—H15	119.00
C6—C7—C9	112.4 (3)	C14ⁱ—C15—H15	119.00
C6—C7—C10	109.2 (3)	C17—C18—H18A	109.00
C8—C7—C9	108.0 (3)	C17—C18—H18B	110.00
C8—C7—C10	108.3 (3)	C17—C18—H18C	109.00
C9—C7—C10	110.0 (3)	H18A—C18—H18B	109.00
C12—C11—C16	122.0 (2)	H18A—C18—H18C	109.00
S2—C12—C11	119.17 (18)	H18B—C18—H18C	110.00
S2—C12—C13ⁱ	120.95 (16)	C17—C19—H19A	109.00
C11—C12—C13ⁱ	119.87 (19)	C17—C19—H19B	109.00
O2—C13—C14	125.4 (2)	C17—C19—H19C	109.00
O2—C13—C12ⁱ	115.73 (18)	H19A—C19—H19B	110.00
C12ⁱ—C13—C14	118.7 (2)	H19A—C19—H19C	110.00
S1—C14—C13	121.56 (18)	H19B—C19—H19C	109.00
S1—C14—C15ⁱ	118.17 (16)	C17—C20—H20A	110.00
C13—C14—C15ⁱ	120.3 (2)	C17—C20—H20B	109.00
C14ⁱ—C15—C16	122.2 (2)	C17—C20—H20C	109.00
C11—C16—C15	116.9 (2)	H20A—C20—H20B	110.00
C11—C16—C17	120.0 (2)	H20A—C20—H20C	109.00
C15—C16—C17	123.1 (2)	H20B—C20—H20C	109.00
C16—C17—C18	108.9 (2)	O4—C23—H23A	110.00
C16—C17—C19	110.7 (2)	O4—C23—H23B	110.00
C16—C17—C20	111.3 (2)	C24—C23—H23A	110.00
C18—C17—C19	109.2 (3)	C24—C23—H23B	110.00
C18—C17—C20	108.8 (2)	H23A—C23—H23B	108.00
C19—C17—C20	107.8 (2)	C23—C24—H24A	110.00
O2—C21—C2	114.06 (18)	C23—C24—H24B	110.00
O2—C21—C22	102.53 (17)	C23—C24—H24C	109.00
O2—C21—C25	106.9 (2)	H24A—C24—H24B	110.00
C2—C21—C22	110.37 (19)	H24A—C24—H24C	109.00
C2—C21—C25	113.09 (18)	H24B—C24—H24C	109.00
C22—C21—C25	109.30 (18)	O6—C26—H26A	109.00
O3—C22—O4	126.5 (2)	O6—C26—H26B	109.00
O3—C22—C21	124.4 (2)	C27—C26—H26A	109.00
O4—C22—C21	109.1 (2)	C27—C26—H26B	109.00
O4—C23—C24	109.6 (3)	H26A—C26—H26B	108.00
O5—C25—O6	125.9 (2)	C26—C27—H27A	109.00
O5—C25—C21	123.6 (2)	C26—C27—H27B	109.00
O6—C25—C21	110.5 (3)	C26—C27—H27C	109.00
O6—C26—C27	111.2 (3)	H27A—C27—H27B	109.00
C2—C1—H1	118.00	H27A—C27—H27C	109.00
C6—C1—H1	118.00	H27B—C27—H27C	109.00

C14—S1—C2—C21	−48.10 (17)	C3—C4—C5—C6	0.2 (3)
C2—S1—C14—C13	22.1 (2)	S2—C4—C5—C6	177.04 (16)
C2—S1—C14—C15ⁱ	−156.25 (19)	C4—C5—C6—C7	−179.6 (2)
C14—S1—C2—C1	−167.61 (17)	C4—C5—C6—C1	3.9 (3)
C14—S1—C2—C3	70.72 (17)	C5—C6—C7—C10	−59.5 (3)
C12—S2—C4—C5	111.75 (19)	C1—C6—C7—C8	−125.1 (3)
C4—S2—C12—C13ⁱ	105.5 (2)	C1—C6—C7—C10	116.9 (3)
C12—S2—C4—C3	−71.32 (18)	C5—C6—C7—C9	178.2 (3)
C4—S2—C12—C11	−76.0 (2)	C5—C6—C7—C8	58.5 (3)
C13—O2—C21—C25	84.7 (2)	C1—C6—C7—C9	−5.4 (4)
C13—O2—C21—C2	−41.1 (3)	C16—C11—C12—S2	−179.19 (18)
C13—O2—C21—C22	−160.4 (2)	C16—C11—C12—C13ⁱ	−0.6 (4)
C21—O2—C13—C14	7.0 (3)	C12—C11—C16—C15	−0.3 (3)
C21—O2—C13—C12ⁱ	−177.6 (2)	C12—C11—C16—C17	−177.8 (2)
C23—O4—C22—O3	−3.3 (4)	S2—C12—C13ⁱ—O2ⁱ	−3.9 (3)
C22—O4—C23—C24	−90.8 (3)	C11—C12—C13ⁱ—C14ⁱ	2.0 (3)
C23—O4—C22—C21	176.2 (2)	S2—C12—C13ⁱ—C14ⁱ	−179.51 (18)
C25—O6—C26—C27	−92.1 (4)	C11—C12—C13ⁱ—O2ⁱ	177.6 (2)
C26—O6—C25—C21	−177.4 (2)	O2—C13—C14—S1	−0.7 (3)
C26—O6—C25—O5	0.9 (4)	C12ⁱ—C13—C14—C15ⁱ	2.4 (3)
C6—C1—C2—C21	124.4 (2)	C12ⁱ—C13—C14—S1	−175.92 (17)
C6—C1—C2—C3	−2.9 (3)	O2—C13—C14—C15ⁱ	177.6 (2)
C2—C1—C6—C7	−178.5 (2)	S1—C14—C15ⁱ—C16ⁱ	176.83 (19)
C2—C1—C6—C5	−2.2 (3)	C13—C14—C15ⁱ—C16ⁱ	−1.6 (4)
C6—C1—C2—S1	−120.2 (2)	C14ⁱ—C15—C16—C11	−0.2 (4)
C1—C2—C21—O2	175.07 (19)	C14ⁱ—C15—C16—C17	177.3 (2)
C1—C2—C3—O1	−171.4 (2)	C15—C16—C17—C20	7.1 (4)
S1—C2—C3—C4	121.69 (18)	C15—C16—C17—C18	−112.9 (3)
C1—C2—C3—C4	6.6 (3)	C15—C16—C17—C19	127.0 (3)
S1—C2—C21—C22	176.10 (15)	C11—C16—C17—C19	−55.6 (3)
S1—C2—C21—C25	−61.1 (2)	C11—C16—C17—C20	−175.5 (2)
S1—C2—C3—O1	−56.3 (2)	C11—C16—C17—C18	64.5 (3)
C3—C2—C21—C25	−178.1 (2)	C2—C21—C22—O4	179.86 (19)
C21—C2—C3—C4	−121.9 (2)	C25—C21—C22—O3	−125.7 (3)
C1—C2—C21—C22	−70.1 (2)	C2—C21—C25—O5	103.3 (3)
S1—C2—C21—O2	61.3 (2)	C2—C21—C25—O6	−78.3 (2)
C3—C2—C21—C22	59.1 (2)	C22—C21—C25—O5	−133.3 (2)
C1—C2—C21—C25	52.7 (3)	C22—C21—C25—O6	45.1 (3)
C3—C2—C21—O2	−55.7 (2)	C25—C21—C22—O4	54.9 (3)
C21—C2—C3—O1	60.2 (3)	O2—C21—C25—O5	−23.0 (3)
C2—C3—C4—C5	−5.5 (3)	O2—C21—C25—O6	155.34 (19)
C2—C3—C4—S2	177.62 (15)	O2—C21—C22—O3	121.2 (3)
O1—C3—C4—C5	172.4 (2)	O2—C21—C22—O4	−58.3 (2)
O1—C3—C4—S2	−4.5 (3)	C2—C21—C22—O3	−0.7 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26A···O4ⁱⁱ	0.97	2.35	3.298 (5)	164

Symmetry code: (ii) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26A···O4ⁱ	0.97	2.35	3.298 (5)	164

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

OAO would like to acknowledge support from the Deanship of Scientific Research, Majmaah University, for funding this work under project No. 1. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Agrawal, Y. K. & Pancholi, J. P. (2007). Indian. J. Chem. Sect. A, 46, 1377–1382. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Higuchi, Y., Narita, M., Niimi, T., Ogawa, N., Hamada, F., Kumagai, H., Iki, N., Miyano, S. & Kabuto, C. (2000). Tetrahedron, 56, 4659–4666. CSD CrossRef CAS Google Scholar
Omran, A. O. & Antipin, I. S. (2014). J. Incl Phenom. Macrocycl Chem. 78, 121–126. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shokova, E. A. & Kovalev, V. V. (2003). Russ. J. Org. Chem. 39, 1–28. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoikov, I. I., Omran, O. A., Solovieva, S. E., Latypov, S. K., Enikeev, K. M., Gubaidullin, A. T., Antipin, I. S. & Konovalov, A. I. (2003). Tetrahedron, 59, 1469–1476. CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o778-o779

doi:10.1107/S205698901501748X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Crystal structure of tetra­ethyl 27,30-dioxo-7,12,20,25-tetra-tert-but­yl-3,16-dioxa-9,22,28,31-tetra­thia­hepta­cyclo­[21.3.1.11,5.14,8.110,14.114,18.117,21]dotriaconta-4,6,8(29),10,12,17,19,21(32),23,25-deca­ene-2,2,15,15-tetra­carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of tetraethyl 27,30-dioxo-7,12,20,25-tetra-tert-butyl-3,16-dioxa-9,22,28,31-tetrathiaheptacyclo[21.3.1.1^1,5.1^4,8.1^10,14.1^14,18.1^17,21]dotriaconta-4,6,8(29),10,12,17,19,21(32),23,25-decaene-2,2,15,15-tetracarboxylate