organic compounds
of 2-methoxy-2-[(4-methoxyphenyl)sulfanyl]-1-phenylethanone
aDepartmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, bInstituto de Química, Universidade de São Paulo, 05508-000 São Paulo, SP, Brazil, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: ignez@ufscar.br
In the title β-thiocarbonyl compound, C16H16O3S, the adjacent methoxy and carbonyl O atoms are [the O—C—C—O torsion angle is 19.8 (4)°] and are separated by 2.582 (3) Å. The dihedral angle between the rings is 40.11 (16)°, and the methoxy group is coplanar with the benzene ring to which it is connected [the C—C—O—C torsion angle is 179.1 (3)°]. The most notable feature of the crystal packing is the formation of methine and methyl C—H⋯O(carbonyl) interactions that lead to a supramolecular chain with a zigzag topology along the c axis. Chains pack with no specific intermolecular interactions between them.
Keywords: crystal structure; C—H⋯O interactions; β-thiocarbonyl; conformation.
CCDC reference: 1416521
1. Related literature
For background to the present structural study, see: Vinhato et al. (2013); Zukerman-Schpector et al. (2008, 2015); Olivato et al. (2013); Distefano et al. (1996). For the structure of the methyl derivative, see: Zukerman-Schpector et al. (2015). For synthetic procedures, see: Ali & McDermott (2002); Zoretic & Soja (1976).
2. Experimental
2.1. Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: Marvinsketch (ChemAxon, 2010) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1416521
https://doi.org/10.1107/S2056989015014565/hg5455sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014565/hg5455Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015014565/hg5455Isup3.cml
As part of our on-going research into the conformational and electronic interactions of β-thio-carbonyl, β-bis-thio-carbonyl and β-thio-β-oxa-carbonyl compounds, e.g. N,N-diethyl-2-[(4'-substituted)phenylthio]acetamides, 1-methyl-3-phenylsulfonyl-2-piperidone, 3,3-bis[(4'-substituted)phenylsulfanyl]-1-methyl-2-piperidones, 2-alkylthio-2-alkylsulfinyl-acetophenones, 2-alkylthio-2-phenylsulfonyl-acetophenones, 2-alkylsulfinyl-2-alkylsulfonyl-acetophenones and 2-methoxy-2-[(4'-methylphenyl)sulfanyl]-1-phenylethan-1-one, utilizing spectroscopic, theoretical and X-ray diffraction methods (Distefano et al., 1996; Zukerman-Schpector et al., 2008; Olivato et al., 2013; Vinhato et al., 2013; Zukerman-Schpector et al., 2015) the title compound was synthesized and its determined.
4'-Methoxythiophenol (5.0 g, 36 mmol) was reacted with bromine (1.1 ml, 20 mmol) in dichloromethane (250 ml) on an hydrated silica gel support (25 g of SiO2 and 12 ml of water) to give 4'-methoxyphenyl disulfide (4.0 g, yield = 80%). A white solid was obtained after filtration and evaporation without further purification (Ali & McDermott, 2002). A solution of 2-methoxy acetophenone (0.80 ml, 5.81 mmol, Sigma-Aldrich) in THF (20 ml), was added drop-wise to a cooled (195 K) solution of diisopropylamine (0.90 ml, 6.39 mmol) and butyllithium (4.30 ml, 5.81 mmol) in THF (30 ml). After 30 minutes, a solution of 4'-methoxyphenyl disulfide (1.780 g, 6.39 mmol) with hexamethylphosphoramide (HMPA) (1.0 ml, 5.81 mmol) dissolved in THF (20 ml) was added drop-wise to the enolate solution (Zoretic & Soja, 1976). After stirring for 3 h, water (50 ml) was added at room temperature and extraction with dichloromethane was performed. The organic layer was then treated with ν(C=O) 1695 (CCl4). 1H NMR (CDCl3, 500 MHz, δ p.p.m.): 3.68 (s, 3H), 3.78 (s, 3H), 5.76 (s, 1H), 6.80–6.82 (m, 2H), 7.24–7.26 (m, 2H), 7.43–7.46 (m, 2H), 7.56–7.59 (m, 1H), 7.94–7.95 (m, 2H). Analysis for C16H16O3S: calculated (%): C 66.64, H 5.59; found (%): C 66.52, H 5.53. High-Resolution MS calculated (M+): 288.0820; found (M+): 288.0821.
of ammonium chloride until neutral pH, and then dried over anhydrous magnesium sulfate. A brown oil was obtained after evaporation of the solvent. Purification through flash with toluene was used to remove the non-polar reactant (disulfide) then acetone to give a mixture of both acetophenones (product and reactant). Crystallization was performed by vapour diffusion of n-hexane into a chloroform solution held at 283 K to give pure product (0.3 g, yield = 40%). Suitable crystals for X-ray diffraction were obtained by same pathway; m.pt: 393.5-394.2 K. IR (cm-1):As part of our on-going research into the conformational and electronic interactions of β-thio-carbonyl, β-bis-thio-carbonyl and β-thio-β-oxa-carbonyl compounds, e.g. N,N-diethyl-2-[(4'-substituted)phenylthio]acetamides, 1-methyl-3-phenylsulfonyl-2-piperidone, 3,3-bis[(4'-substituted)phenylsulfanyl]-1-methyl-2-piperidones, 2-alkylthio-2-alkylsulfinyl-acetophenones, 2-alkylthio-2-phenylsulfonyl-acetophenones, 2-alkylsulfinyl-2-alkylsulfonyl-acetophenones and 2-methoxy-2-[(4'-methylphenyl)sulfanyl]-1-phenylethan-1-one, utilizing spectroscopic, theoretical and X-ray diffraction methods (Distefano et al., 1996; Zukerman-Schpector et al., 2008; Olivato et al., 2013; Vinhato et al., 2013; Zukerman-Schpector et al., 2015) the title compound was synthesized and its determined.
For background to the present structural study, see: Vinhato et al. (2013); Zukerman-Schpector et al. (2008, 2015); Olivato et al. (2013); Distefano et al. (1996). For the structure of the methyl derivative, see: Zukerman-Schpector et al. (2015). For synthetic procedures, see: Ali & McDermott (2002); Zoretic & Soja (1976).
4'-Methoxythiophenol (5.0 g, 36 mmol) was reacted with bromine (1.1 ml, 20 mmol) in dichloromethane (250 ml) on an hydrated silica gel support (25 g of SiO2 and 12 ml of water) to give 4'-methoxyphenyl disulfide (4.0 g, yield = 80%). A white solid was obtained after filtration and evaporation without further purification (Ali & McDermott, 2002). A solution of 2-methoxy acetophenone (0.80 ml, 5.81 mmol, Sigma-Aldrich) in THF (20 ml), was added drop-wise to a cooled (195 K) solution of diisopropylamine (0.90 ml, 6.39 mmol) and butyllithium (4.30 ml, 5.81 mmol) in THF (30 ml). After 30 minutes, a solution of 4'-methoxyphenyl disulfide (1.780 g, 6.39 mmol) with hexamethylphosphoramide (HMPA) (1.0 ml, 5.81 mmol) dissolved in THF (20 ml) was added drop-wise to the enolate solution (Zoretic & Soja, 1976). After stirring for 3 h, water (50 ml) was added at room temperature and extraction with dichloromethane was performed. The organic layer was then treated with ν(C=O) 1695 (CCl4). 1H NMR (CDCl3, 500 MHz, δ p.p.m.): 3.68 (s, 3H), 3.78 (s, 3H), 5.76 (s, 1H), 6.80–6.82 (m, 2H), 7.24–7.26 (m, 2H), 7.43–7.46 (m, 2H), 7.56–7.59 (m, 1H), 7.94–7.95 (m, 2H). Analysis for C16H16O3S: calculated (%): C 66.64, H 5.59; found (%): C 66.52, H 5.53. High-Resolution MS calculated (M+): 288.0820; found (M+): 288.0821.
of ammonium chloride until neutral pH, and then dried over anhydrous magnesium sulfate. A brown oil was obtained after evaporation of the solvent. Purification through flash with toluene was used to remove the non-polar reactant (disulfide) then acetone to give a mixture of both acetophenones (product and reactant). Crystallization was performed by vapour diffusion of n-hexane into a chloroform solution held at 283 K to give pure product (0.3 g, yield = 40%). Suitable crystals for X-ray diffraction were obtained by same pathway; m.pt: 393.5-394.2 K. IR (cm-1): detailsCarbon-bound H-atoms were placed in calculated positions (C—H = 0.93–0.98 Å) and were included in the
in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C).Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: Marvinsketch (ChemAxon, 2010) and publCIF (Westrip, 2010).C16H16O3S | Dx = 1.327 Mg m−3 |
Mr = 288.35 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 2745 reflections |
a = 18.769 (3) Å | θ = 2.2–25.1° |
b = 7.643 (1) Å | µ = 0.23 mm−1 |
c = 10.0578 (16) Å | T = 296 K |
V = 1442.8 (4) Å3 | Irregular, colourless |
Z = 4 | 0.37 × 0.16 × 0.09 mm |
F(000) = 608 |
Bruker APEXII CCD diffractometer | 1627 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 25.4°, θmin = 2.2° |
Tmin = 0.618, Tmax = 0.745 | h = −22→22 |
6725 measured reflections | k = −8→9 |
1935 independent reflections | l = −7→12 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0337P)2 + 0.2623P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.076 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.12 e Å−3 |
1935 reflections | Δρmin = −0.14 e Å−3 |
183 parameters | Absolute structure: Flack x determined using 418 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.09 (4) |
C16H16O3S | V = 1442.8 (4) Å3 |
Mr = 288.35 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 18.769 (3) Å | µ = 0.23 mm−1 |
b = 7.643 (1) Å | T = 296 K |
c = 10.0578 (16) Å | 0.37 × 0.16 × 0.09 mm |
Bruker APEXII CCD diffractometer | 1935 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1627 reflections with I > 2σ(I) |
Tmin = 0.618, Tmax = 0.745 | Rint = 0.026 |
6725 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.076 | Δρmax = 0.12 e Å−3 |
S = 1.04 | Δρmin = −0.14 e Å−3 |
1935 reflections | Absolute structure: Flack x determined using 418 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
183 parameters | Absolute structure parameter: 0.09 (4) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.56536 (5) | 0.23724 (10) | 0.74255 (12) | 0.0585 (3) | |
O1 | 0.53351 (13) | 0.6345 (3) | 0.9109 (3) | 0.0608 (6) | |
O2 | 0.44516 (10) | 0.4243 (3) | 0.7959 (3) | 0.0588 (6) | |
O3 | 0.67048 (13) | 0.2149 (3) | 1.2961 (3) | 0.0702 (8) | |
C1 | 0.7294 (2) | 0.8300 (5) | 0.6168 (5) | 0.0670 (11) | |
H1 | 0.7687 | 0.8842 | 0.5784 | 0.080* | |
C2 | 0.70618 (18) | 0.8808 (4) | 0.7391 (5) | 0.0707 (11) | |
H2 | 0.7294 | 0.9710 | 0.7834 | 0.085* | |
C3 | 0.64887 (17) | 0.8002 (4) | 0.7975 (4) | 0.0566 (9) | |
H3 | 0.6338 | 0.8355 | 0.8814 | 0.068* | |
C4 | 0.61332 (15) | 0.6666 (4) | 0.7325 (4) | 0.0441 (7) | |
C5 | 0.63593 (19) | 0.6186 (5) | 0.6074 (4) | 0.0587 (9) | |
H5 | 0.6117 | 0.5320 | 0.5608 | 0.070* | |
C6 | 0.6949 (2) | 0.6995 (5) | 0.5506 (4) | 0.0696 (11) | |
H6 | 0.7108 | 0.6644 | 0.4672 | 0.083* | |
C7 | 0.55159 (15) | 0.5857 (4) | 0.8007 (3) | 0.0439 (7) | |
C8 | 0.51146 (15) | 0.4382 (3) | 0.7343 (4) | 0.0455 (7) | |
H8 | 0.5041 | 0.4685 | 0.6407 | 0.055* | |
C9 | 0.3949 (2) | 0.3296 (5) | 0.7185 (4) | 0.0718 (12) | |
H9A | 0.4129 | 0.2143 | 0.7012 | 0.108* | |
H9B | 0.3871 | 0.3894 | 0.6358 | 0.108* | |
H9C | 0.3507 | 0.3213 | 0.7663 | 0.108* | |
C10 | 0.59396 (18) | 0.2334 (4) | 0.9103 (4) | 0.0448 (8) | |
C11 | 0.55035 (17) | 0.1718 (4) | 1.0103 (4) | 0.0474 (8) | |
H11 | 0.5045 | 0.1348 | 0.9897 | 0.057* | |
C12 | 0.57361 (17) | 0.1641 (4) | 1.1405 (4) | 0.0493 (9) | |
H12 | 0.5434 | 0.1230 | 1.2068 | 0.059* | |
C13 | 0.64116 (18) | 0.2170 (4) | 1.1714 (4) | 0.0491 (9) | |
C14 | 0.68553 (18) | 0.2783 (4) | 1.0714 (4) | 0.0610 (10) | |
H14 | 0.7316 | 0.3143 | 1.0919 | 0.073* | |
C15 | 0.66189 (18) | 0.2860 (4) | 0.9429 (4) | 0.0550 (9) | |
H15 | 0.6921 | 0.3273 | 0.8767 | 0.066* | |
C16 | 0.6275 (2) | 0.1561 (6) | 1.4024 (4) | 0.0749 (11) | |
H16A | 0.6538 | 0.1639 | 1.4841 | 0.112* | |
H16B | 0.6138 | 0.0367 | 1.3871 | 0.112* | |
H16C | 0.5856 | 0.2277 | 1.4083 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0873 (6) | 0.0513 (4) | 0.0370 (5) | 0.0083 (4) | −0.0003 (5) | −0.0065 (5) |
O1 | 0.0732 (14) | 0.0705 (15) | 0.0387 (16) | 0.0031 (13) | 0.0019 (12) | −0.0129 (13) |
O2 | 0.0561 (13) | 0.0760 (15) | 0.0444 (16) | −0.0089 (11) | 0.0015 (13) | −0.0003 (13) |
O3 | 0.0628 (15) | 0.0992 (19) | 0.0486 (18) | 0.0162 (14) | −0.0127 (15) | 0.0049 (15) |
C1 | 0.056 (2) | 0.067 (2) | 0.078 (4) | −0.0075 (19) | −0.006 (2) | 0.015 (2) |
C2 | 0.061 (2) | 0.061 (2) | 0.090 (4) | −0.0085 (17) | −0.010 (3) | −0.010 (3) |
C3 | 0.061 (2) | 0.0537 (18) | 0.055 (3) | 0.0065 (17) | −0.007 (2) | −0.0090 (18) |
C4 | 0.0491 (16) | 0.0415 (14) | 0.042 (2) | 0.0075 (13) | −0.0069 (16) | −0.0003 (17) |
C5 | 0.073 (2) | 0.064 (2) | 0.039 (2) | −0.0115 (18) | −0.0002 (19) | −0.0035 (18) |
C6 | 0.075 (2) | 0.083 (3) | 0.051 (3) | −0.001 (2) | 0.009 (2) | 0.008 (2) |
C7 | 0.0561 (17) | 0.0455 (16) | 0.030 (2) | 0.0080 (14) | −0.0052 (17) | 0.0020 (15) |
C8 | 0.0552 (17) | 0.0530 (16) | 0.0282 (17) | −0.0006 (14) | −0.0009 (16) | 0.0002 (18) |
C9 | 0.070 (2) | 0.081 (2) | 0.065 (3) | −0.020 (2) | −0.009 (2) | 0.002 (2) |
C10 | 0.0572 (19) | 0.0356 (16) | 0.041 (2) | 0.0100 (14) | 0.0040 (16) | −0.0001 (15) |
C11 | 0.0507 (18) | 0.0478 (18) | 0.044 (2) | −0.0021 (14) | 0.0007 (16) | 0.0018 (16) |
C12 | 0.0536 (19) | 0.0496 (19) | 0.045 (2) | 0.0071 (15) | 0.0068 (16) | 0.0041 (16) |
C13 | 0.053 (2) | 0.055 (2) | 0.040 (2) | 0.0139 (16) | −0.0016 (18) | 0.0033 (16) |
C14 | 0.0455 (18) | 0.075 (2) | 0.063 (3) | 0.0020 (17) | −0.004 (2) | 0.008 (2) |
C15 | 0.055 (2) | 0.060 (2) | 0.050 (3) | 0.0023 (17) | 0.0125 (19) | 0.0059 (18) |
C16 | 0.083 (2) | 0.103 (3) | 0.039 (3) | 0.027 (3) | −0.001 (2) | 0.005 (2) |
S1—C10 | 1.771 (4) | C7—C8 | 1.511 (4) |
S1—C8 | 1.841 (3) | C8—H8 | 0.9800 |
O1—C7 | 1.217 (4) | C9—H9A | 0.9600 |
O2—C8 | 1.394 (3) | C9—H9B | 0.9600 |
O2—C9 | 1.421 (4) | C9—H9C | 0.9600 |
O3—C13 | 1.370 (4) | C10—C15 | 1.376 (5) |
O3—C16 | 1.413 (5) | C10—C11 | 1.380 (5) |
C1—C2 | 1.361 (6) | C11—C12 | 1.381 (5) |
C1—C6 | 1.363 (6) | C11—H11 | 0.9300 |
C1—H1 | 0.9300 | C12—C13 | 1.367 (5) |
C2—C3 | 1.372 (5) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.387 (5) |
C3—C4 | 1.384 (4) | C14—C15 | 1.368 (6) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.377 (5) | C15—H15 | 0.9300 |
C4—C7 | 1.482 (4) | C16—H16A | 0.9600 |
C5—C6 | 1.390 (5) | C16—H16B | 0.9600 |
C5—H5 | 0.9300 | C16—H16C | 0.9600 |
C6—H6 | 0.9300 | ||
C10—S1—C8 | 102.90 (15) | O2—C9—H9A | 109.5 |
C8—O2—C9 | 112.8 (3) | O2—C9—H9B | 109.5 |
C13—O3—C16 | 117.8 (3) | H9A—C9—H9B | 109.5 |
C2—C1—C6 | 119.8 (4) | O2—C9—H9C | 109.5 |
C2—C1—H1 | 120.1 | H9A—C9—H9C | 109.5 |
C6—C1—H1 | 120.1 | H9B—C9—H9C | 109.5 |
C1—C2—C3 | 120.7 (4) | C15—C10—C11 | 118.4 (3) |
C1—C2—H2 | 119.7 | C15—C10—S1 | 120.2 (3) |
C3—C2—H2 | 119.7 | C11—C10—S1 | 121.4 (3) |
C2—C3—C4 | 120.4 (4) | C10—C11—C12 | 121.2 (3) |
C2—C3—H3 | 119.8 | C10—C11—H11 | 119.4 |
C4—C3—H3 | 119.8 | C12—C11—H11 | 119.4 |
C5—C4—C3 | 118.6 (3) | C13—C12—C11 | 119.8 (3) |
C5—C4—C7 | 123.6 (3) | C13—C12—H12 | 120.1 |
C3—C4—C7 | 117.8 (3) | C11—C12—H12 | 120.1 |
C4—C5—C6 | 120.2 (4) | C12—C13—O3 | 125.3 (3) |
C4—C5—H5 | 119.9 | C12—C13—C14 | 119.5 (4) |
C6—C5—H5 | 119.9 | O3—C13—C14 | 115.2 (3) |
C1—C6—C5 | 120.2 (4) | C15—C14—C13 | 120.3 (4) |
C1—C6—H6 | 119.9 | C15—C14—H14 | 119.8 |
C5—C6—H6 | 119.9 | C13—C14—H14 | 119.8 |
O1—C7—C4 | 120.8 (3) | C14—C15—C10 | 120.8 (3) |
O1—C7—C8 | 119.4 (3) | C14—C15—H15 | 119.6 |
C4—C7—C8 | 119.8 (3) | C10—C15—H15 | 119.6 |
O2—C8—C7 | 107.8 (2) | O3—C16—H16A | 109.5 |
O2—C8—S1 | 114.0 (2) | O3—C16—H16B | 109.5 |
C7—C8—S1 | 109.2 (2) | H16A—C16—H16B | 109.5 |
O2—C8—H8 | 108.6 | O3—C16—H16C | 109.5 |
C7—C8—H8 | 108.6 | H16A—C16—H16C | 109.5 |
S1—C8—H8 | 108.6 | H16B—C16—H16C | 109.5 |
C6—C1—C2—C3 | 0.9 (6) | C4—C7—C8—S1 | 74.1 (3) |
C1—C2—C3—C4 | −0.5 (5) | C10—S1—C8—O2 | −74.0 (3) |
C2—C3—C4—C5 | −1.1 (5) | C10—S1—C8—C7 | 46.6 (3) |
C2—C3—C4—C7 | −179.6 (3) | C8—S1—C10—C15 | −101.2 (3) |
C3—C4—C5—C6 | 2.2 (5) | C8—S1—C10—C11 | 81.4 (3) |
C7—C4—C5—C6 | −179.3 (3) | C15—C10—C11—C12 | 0.6 (4) |
C2—C1—C6—C5 | 0.2 (6) | S1—C10—C11—C12 | 178.0 (2) |
C4—C5—C6—C1 | −1.9 (6) | C10—C11—C12—C13 | −0.5 (5) |
C5—C4—C7—O1 | −179.3 (3) | C11—C12—C13—O3 | −179.7 (3) |
C3—C4—C7—O1 | −0.8 (4) | C11—C12—C13—C14 | 0.2 (5) |
C5—C4—C7—C8 | 2.1 (4) | C16—O3—C13—C12 | −1.1 (5) |
C3—C4—C7—C8 | −179.4 (3) | C16—O3—C13—C14 | 179.1 (3) |
C9—O2—C8—C7 | 161.9 (3) | C12—C13—C14—C15 | 0.1 (5) |
C9—O2—C8—S1 | −76.7 (3) | O3—C13—C14—C15 | 179.9 (3) |
O1—C7—C8—O2 | 19.8 (4) | C13—C14—C15—C10 | 0.0 (5) |
C4—C7—C8—O2 | −161.5 (2) | C11—C10—C15—C14 | −0.3 (5) |
O1—C7—C8—S1 | −104.5 (3) | S1—C10—C15—C14 | −177.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.98 | 2.54 | 3.406 (5) | 147 |
C16—H16C···O1ii | 0.96 | 2.47 | 3.421 (5) | 170 |
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) −x+1, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.98 | 2.54 | 3.406 (5) | 147 |
C16—H16C···O1ii | 0.96 | 2.47 | 3.421 (5) | 170 |
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) −x+1, −y+1, z+1/2. |
Acknowledgements
We thank Professor Regina H. A. Santos from IQSC–USP for the X-ray data collection. The Brazilian agencies CNPq (306121/2013-2 to IC; 301180/2013-0 to PRO), FAPESP and CAPES are acknowledged for support.
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