organic compounds
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
of tetraethyl 27,30-dioxo-7,12,20,25-tetra-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
The 54H64O12S4, consists of one half of the molecule, which is located on an inversion centre. The heterocyclic six-membered ring adopts a distorted 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.
of the title compound, CKeywords: crystal structure; calixarenes; macrocycles; hydrogen bonding.
CCDC reference: 1425819
1. Related literature
For industrial application of ); Stoikov et al. (2003). For macrocyclic reactions of see: Agrawal & Pancholi (2007); Higuchi et al. (2000); Omran & Antipin (2014).
see: Shokova & Kovalev (20032. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2014); cell 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
10.1107/S205698901501748X/is5424sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S205698901501748X/is5424Isup2.hkl
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.
All H atoms were placed in calculated positions with C—H = 0.93–0.97 Å and refined as riding with Uiso(H) = 1.2 or 1.5Ueq (C). The (-2 5 1), (-2 5 0), (2 - 2 4), (-3 - 7 1), (-4 7 1), (1 6 0), (-5 1 2), (1 - 2 3), (-3 - 1 8), (5 - 4 3), (0 - 3 2), (-2 5 4), (1–8 3), (3 4 7), (-8 - 6 2), (5 - 10 4), (1 6 4), (7 - 3 2), (2 - 8 1), (6 0 2), (-1 - 9 4), (-5 4 8), (-7 6 12), (-8 3 0), (-3 2 8) and (-8 0 2) reflections were omitted owing to very bad agreement.
Data collection: CrysAlis PRO (Agilent, 2014); cell
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).C54H64O12S4 | Z = 1 |
Mr = 1033.29 | F(000) = 548 |
Triclinic, P1 | Dx = 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 |
Agilent Xcalibur, Eos, Gemini diffractometer | 8908 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 6481 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 32.8°, θmin = 3.3° |
ω scans | h = −14→16 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −16→17 |
Tmin = 0.715, Tmax = 0.967 | l = −18→17 |
16365 measured reflections |
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(Fo2) + (0.0595P)2 + 1.2423P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
8908 reflections | Δρmax = 0.58 e Å−3 |
324 parameters | Δρmin = −0.38 e Å−3 |
C54H64O12S4 | γ = 105.884 (4)° |
Mr = 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)° |
Agilent Xcalibur, Eos, Gemini diffractometer | 8908 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 6481 reflections with I > 2σ(I) |
Tmin = 0.715, Tmax = 0.967 | Rint = 0.036 |
16365 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.58 e Å−3 |
8908 reflections | Δρmin = −0.38 e Å−3 |
324 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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. |
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. |
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.
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 QT = 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).