organic compounds
E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2-one
of (3aBioMat-Departmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, bInstituto de Química, Universidade Estadual de Campinas, CP 6154, 13083-970 Campinas, SP, Brazil, cDepartmento de Qímica, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: ignez@ufscar.br
In the title compound, C17H14N2O6, the conformation about the C=C double bond [1.345 (2) Å] is E, with the ketone moiety almost coplanar [C—C—C—C torsion angle = 9.5 (2)°] along with the phenyl ring [C—C—C—C = 5.9 (2)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The 4-nitro moiety is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 4.2 (2)°], whereas the one in the ortho position is twisted [O—N—C—C = 138.28 (13)°]. The molecules associate via C—H⋯O interactions, involving both O atoms from the 2-nitro group, to form a helical supramolecular chain along [010]. Nitro–nitro N⋯O interactions [2.8461 (19) Å] connect the chains into layers that stack along [001].
Keywords: crystal structure; hydrogen bonding; N⋯O interactions.
CCDC reference: 1020026
1. Related literature
For background to biotransformations mediated by Saccharomyces cerevisiae, see: Rodrigues et al. (2004); de Paula et al. (2013). For a related structure, see: Zukerman-Schpector et al. (2014). For interactions between nitro groups, see: Daszkiewicz (2013).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1020026
10.1107/S1600536814018819/hg5406sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018819/hg5406Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018819/hg5406Isup3.cml
In the context of the study of biotransformation reactions mediated by Saccharomyces cerevisiae, such as the bio-reduction of α-haloketones and enones (Rodrigues et al., 2004), the title compound, (3E)-3-(2,4-dinitrophenoxymethyl)-4-phenylbut-3-en-2- one, (I), as well as its 4-nitrophenylmethyl analogue, i.e. (3E)-3-(4-nitrophenoxymethyl)-4-phenylbut-3-en-2-one, (II), (Zukerman-Schpector et al. 2014), were synthesised to be used as substrates in order to compare their behaviour with that of the 3-halomethyl-4-phenyl-3-buten-2-ones analogues (de Paula et al., 2013). Herein, the determination and spectroscopic details of (I) are described.
In (I), the conformation about the C═C double bond [1.345 (2) Å] is E. The ketone moiety almost co-planar [C11–C8–C9–C10 torsion angle = 9.5 (2) °] with the double bond but the phenyl ring is twisted [C8–C11–C12–C17 = -150.23 (16)°]. The aromatic rings are almost perpendicular to each other [dihedral angle = 86.66 (7)°]. The p-nitro moiety is approximately co-planar with the benzene ring to which it is attached [O3–N1–C4–C5 = -175.29 (14) °] while the the one in the o-position is twisted [O5–N2–C2–C3 = -40.76 (17)°].
Fig. 2 shows and overlay diagram of (I) and the inverted molecule of (II) (Zukerman-Schpector et al. 2014). Clearly, the two molecules adopt very similar conformations.
In the crystal packing, molecules associate via C—H···O interactions, whereby the O atoms of the o-nitro group interact with H derived from a benzene or a phenyl ring, leading to a supramolecular helical chain along [0 1 0]; Fig. 2. There also N···O5 interactions [2.8461 (19) Å], i.e. nitro···nitro interactions (Daszkiewicz, 2013), that link the chains into a layer. Layers stack along [0 0 1] without specific intermolecular interactions between them, Fig. 3.
Potassium carbonate (232 mg, 2.4 mmol) and 2,4-dinitrophenol (368 mg, 2 mmol) were added to a solution of 4-nitrophenol (1.53 g, 11 mmol) and 3-bromomethyl-4-phenyl-3-buten-2-one (478 mg, 2 mmol) in dry acetone (4 mL). The reaction mixture was stirred for 16 hours and the filtered. The solvent was evaporated and the residue was purified by δ 2.52 (3H, s), 5.12 (2H, s), 7.41 (d, 1H, J = 9.2 Hz), 7.43-7.56 (5H, m), 7.99 (1H, s), 8.42 (dd, 1H, J = 2.8, 9.2 Hz), 8.72 (d, 1H, J = 2.8 Hz). 13C NMR (CD2Cl2, 150 MHz): δ 26.2, 64.7, 116.1, 122.3, 129.5, 129.7, 130.2, 130.8, 134.5, 134.6, 139.8, 140.9, 148.1, 157.0, 198.4.
(hexane/EtOAc, 80:20) to afford the product as a colourless solid in 75% yield. The product was recrystallized by slow evaporation of a 2:1 dichloromethane/hexane mixture. M.pt: 442.2–442.8 K. 1H NMR (CD2Cl2, 400 MHz):Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).C17H14N2O6 | F(000) = 712 |
Mr = 342.30 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6161 reflections |
a = 12.8459 (6) Å | θ = 2.9–25.3° |
b = 7.6983 (4) Å | µ = 0.11 mm−1 |
c = 19.4283 (8) Å | T = 290 K |
β = 122.254 (2)° | Irregular, colourless |
V = 1624.82 (14) Å3 | 0.66 × 0.45 × 0.28 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 2957 independent reflections |
Radiation source: fine-focus sealed tube | 2630 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω and ϕ scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→15 |
Tmin = 0.699, Tmax = 0.745 | k = −7→9 |
10435 measured reflections | l = −23→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.047P)2 + 0.4196P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2957 reflections | Δρmax = 0.20 e Å−3 |
228 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0323 (19) |
C17H14N2O6 | V = 1624.82 (14) Å3 |
Mr = 342.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.8459 (6) Å | µ = 0.11 mm−1 |
b = 7.6983 (4) Å | T = 290 K |
c = 19.4283 (8) Å | 0.66 × 0.45 × 0.28 mm |
β = 122.254 (2)° |
Bruker Kappa APEXII CCD diffractometer | 2957 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2630 reflections with I > 2σ(I) |
Tmin = 0.699, Tmax = 0.745 | Rint = 0.019 |
10435 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.20 e Å−3 |
2957 reflections | Δρmin = −0.21 e Å−3 |
228 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.93401 (11) | 0.15407 (17) | 0.37127 (8) | 0.0384 (3) | |
C2 | 0.99377 (11) | 0.00425 (16) | 0.36899 (7) | 0.0364 (3) | |
C3 | 1.08837 (11) | 0.01022 (18) | 0.35523 (8) | 0.0409 (3) | |
H3 | 1.1239 | −0.0912 | 0.3510 | 0.049* | |
C4 | 1.12866 (12) | 0.17061 (19) | 0.34788 (8) | 0.0436 (3) | |
C5 | 1.07599 (14) | 0.3221 (2) | 0.35327 (9) | 0.0509 (4) | |
H5 | 1.1062 | 0.4292 | 0.3496 | 0.061* | |
C6 | 0.97836 (14) | 0.31403 (18) | 0.36410 (10) | 0.0494 (4) | |
H6 | 0.9418 | 0.4161 | 0.3666 | 0.059* | |
C7 | 0.76361 (13) | 0.28733 (18) | 0.36901 (10) | 0.0463 (3) | |
H7A | 0.7331 | 0.3422 | 0.3167 | 0.056* | |
H7B | 0.8140 | 0.3705 | 0.4115 | 0.056* | |
C8 | 0.65850 (12) | 0.22873 (19) | 0.37591 (9) | 0.0437 (3) | |
C9 | 0.68382 (13) | 0.2244 (2) | 0.46004 (9) | 0.0503 (4) | |
C10 | 0.58981 (16) | 0.1491 (3) | 0.47503 (11) | 0.0656 (5) | |
H10A | 0.6229 | 0.1458 | 0.5325 | 0.098* | |
H10B | 0.5694 | 0.0334 | 0.4534 | 0.098* | |
H10C | 0.5171 | 0.2199 | 0.4488 | 0.098* | |
C11 | 0.54588 (13) | 0.18897 (19) | 0.31208 (9) | 0.0464 (3) | |
H11 | 0.4877 | 0.1628 | 0.3251 | 0.056* | |
C12 | 0.50092 (13) | 0.18058 (18) | 0.22527 (9) | 0.0447 (3) | |
C13 | 0.57329 (14) | 0.1286 (2) | 0.19522 (9) | 0.0502 (4) | |
H13 | 0.6557 | 0.1012 | 0.2312 | 0.060* | |
C14 | 0.52360 (15) | 0.1174 (2) | 0.11257 (10) | 0.0568 (4) | |
H14 | 0.5729 | 0.0830 | 0.0933 | 0.068* | |
C15 | 0.40169 (16) | 0.1568 (2) | 0.05828 (10) | 0.0596 (4) | |
H15 | 0.3690 | 0.1496 | 0.0026 | 0.071* | |
C16 | 0.32823 (15) | 0.2069 (2) | 0.08653 (10) | 0.0613 (4) | |
H16 | 0.2458 | 0.2337 | 0.0500 | 0.074* | |
C17 | 0.37725 (14) | 0.2172 (2) | 0.16927 (10) | 0.0539 (4) | |
H17 | 0.3268 | 0.2492 | 0.1880 | 0.065* | |
N1 | 1.22919 (11) | 0.1784 (2) | 0.33327 (8) | 0.0572 (4) | |
N2 | 0.95589 (10) | −0.16711 (15) | 0.38003 (7) | 0.0443 (3) | |
O1 | 0.83551 (8) | 0.13359 (12) | 0.37729 (6) | 0.0459 (3) | |
O2 | 0.78088 (11) | 0.27977 (19) | 0.51669 (7) | 0.0716 (4) | |
O3 | 1.26869 (11) | 0.0420 (2) | 0.32347 (8) | 0.0767 (4) | |
O4 | 1.26880 (12) | 0.32170 (19) | 0.33128 (9) | 0.0825 (4) | |
O5 | 0.95090 (13) | −0.28306 (15) | 0.33557 (8) | 0.0716 (4) | |
O6 | 0.93475 (11) | −0.18635 (15) | 0.43354 (8) | 0.0673 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0332 (6) | 0.0384 (7) | 0.0442 (7) | −0.0002 (5) | 0.0209 (6) | 0.0030 (5) |
C2 | 0.0316 (6) | 0.0352 (7) | 0.0391 (6) | −0.0014 (5) | 0.0167 (5) | 0.0027 (5) |
C3 | 0.0341 (6) | 0.0469 (8) | 0.0400 (7) | 0.0039 (6) | 0.0187 (6) | 0.0018 (6) |
C4 | 0.0338 (6) | 0.0564 (9) | 0.0412 (7) | −0.0039 (6) | 0.0204 (6) | 0.0042 (6) |
C5 | 0.0478 (8) | 0.0461 (8) | 0.0605 (9) | −0.0090 (6) | 0.0301 (7) | 0.0067 (7) |
C6 | 0.0496 (8) | 0.0357 (7) | 0.0681 (10) | 0.0009 (6) | 0.0349 (8) | 0.0041 (7) |
C7 | 0.0426 (7) | 0.0407 (8) | 0.0599 (9) | 0.0080 (6) | 0.0302 (7) | 0.0032 (6) |
C8 | 0.0405 (7) | 0.0443 (8) | 0.0518 (8) | 0.0104 (6) | 0.0284 (6) | 0.0041 (6) |
C9 | 0.0443 (8) | 0.0550 (9) | 0.0509 (8) | 0.0158 (7) | 0.0248 (7) | 0.0081 (7) |
C10 | 0.0647 (10) | 0.0875 (13) | 0.0582 (10) | 0.0071 (9) | 0.0419 (9) | 0.0055 (9) |
C11 | 0.0418 (7) | 0.0524 (8) | 0.0542 (8) | 0.0061 (6) | 0.0318 (7) | 0.0013 (6) |
C12 | 0.0436 (7) | 0.0443 (8) | 0.0517 (8) | 0.0024 (6) | 0.0291 (7) | 0.0003 (6) |
C13 | 0.0470 (8) | 0.0546 (9) | 0.0541 (8) | 0.0103 (7) | 0.0304 (7) | 0.0040 (7) |
C14 | 0.0668 (10) | 0.0592 (10) | 0.0597 (9) | 0.0106 (8) | 0.0440 (8) | 0.0052 (8) |
C15 | 0.0666 (10) | 0.0640 (11) | 0.0492 (9) | 0.0053 (8) | 0.0317 (8) | 0.0051 (7) |
C16 | 0.0463 (8) | 0.0755 (12) | 0.0553 (9) | 0.0049 (8) | 0.0226 (7) | 0.0018 (8) |
C17 | 0.0418 (7) | 0.0650 (10) | 0.0591 (9) | 0.0018 (7) | 0.0298 (7) | −0.0040 (7) |
N1 | 0.0398 (7) | 0.0847 (11) | 0.0497 (7) | −0.0076 (7) | 0.0256 (6) | 0.0055 (7) |
N2 | 0.0342 (6) | 0.0364 (6) | 0.0536 (7) | 0.0010 (5) | 0.0177 (5) | 0.0058 (5) |
O1 | 0.0380 (5) | 0.0394 (5) | 0.0685 (6) | 0.0048 (4) | 0.0339 (5) | 0.0072 (4) |
O2 | 0.0542 (7) | 0.0928 (10) | 0.0513 (7) | 0.0044 (6) | 0.0170 (6) | 0.0071 (6) |
O3 | 0.0611 (7) | 0.0984 (10) | 0.0919 (9) | 0.0169 (7) | 0.0550 (7) | 0.0151 (8) |
O4 | 0.0699 (8) | 0.0988 (11) | 0.0971 (10) | −0.0359 (7) | 0.0567 (8) | −0.0084 (8) |
O5 | 0.0896 (9) | 0.0395 (6) | 0.0671 (8) | −0.0070 (6) | 0.0294 (7) | −0.0080 (5) |
O6 | 0.0747 (8) | 0.0542 (7) | 0.0984 (9) | 0.0033 (6) | 0.0632 (8) | 0.0199 (6) |
C1—O1 | 1.3405 (15) | C10—H10A | 0.9600 |
C1—C6 | 1.3947 (18) | C10—H10B | 0.9600 |
C1—C2 | 1.3993 (18) | C10—H10C | 0.9600 |
C2—C3 | 1.3773 (17) | C11—C12 | 1.464 (2) |
C2—N2 | 1.4610 (16) | C11—H11 | 0.9300 |
C3—C4 | 1.375 (2) | C12—C17 | 1.394 (2) |
C3—H3 | 0.9300 | C12—C13 | 1.3945 (19) |
C4—C5 | 1.380 (2) | C13—C14 | 1.378 (2) |
C4—N1 | 1.4638 (17) | C13—H13 | 0.9300 |
C5—C6 | 1.379 (2) | C14—C15 | 1.376 (2) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | C15—C16 | 1.376 (2) |
C7—O1 | 1.4565 (16) | C15—H15 | 0.9300 |
C7—C8 | 1.4959 (19) | C16—C17 | 1.381 (2) |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | C17—H17 | 0.9300 |
C8—C11 | 1.345 (2) | N1—O4 | 1.2242 (18) |
C8—C9 | 1.487 (2) | N1—O3 | 1.2242 (19) |
C9—O2 | 1.2176 (19) | N2—O6 | 1.2156 (16) |
C9—C10 | 1.502 (2) | N2—O5 | 1.2198 (16) |
O1—C1—C6 | 124.58 (12) | H10A—C10—H10B | 109.5 |
O1—C1—C2 | 117.72 (11) | C9—C10—H10C | 109.5 |
C6—C1—C2 | 117.66 (12) | H10A—C10—H10C | 109.5 |
C3—C2—C1 | 122.31 (12) | H10B—C10—H10C | 109.5 |
C3—C2—N2 | 117.14 (11) | C8—C11—C12 | 129.87 (13) |
C1—C2—N2 | 120.55 (11) | C8—C11—H11 | 115.1 |
C4—C3—C2 | 118.04 (12) | C12—C11—H11 | 115.1 |
C4—C3—H3 | 121.0 | C17—C12—C13 | 117.91 (13) |
C2—C3—H3 | 121.0 | C17—C12—C11 | 118.36 (12) |
C3—C4—C5 | 121.58 (12) | C13—C12—C11 | 123.63 (13) |
C3—C4—N1 | 118.47 (13) | C14—C13—C12 | 120.53 (14) |
C5—C4—N1 | 119.95 (13) | C14—C13—H13 | 119.7 |
C6—C5—C4 | 119.75 (13) | C12—C13—H13 | 119.7 |
C6—C5—H5 | 120.1 | C15—C14—C13 | 120.61 (14) |
C4—C5—H5 | 120.1 | C15—C14—H14 | 119.7 |
C5—C6—C1 | 120.54 (13) | C13—C14—H14 | 119.7 |
C5—C6—H6 | 119.7 | C16—C15—C14 | 119.88 (15) |
C1—C6—H6 | 119.7 | C16—C15—H15 | 120.1 |
O1—C7—C8 | 107.14 (11) | C14—C15—H15 | 120.1 |
O1—C7—H7A | 110.3 | C15—C16—C17 | 119.79 (15) |
C8—C7—H7A | 110.3 | C15—C16—H16 | 120.1 |
O1—C7—H7B | 110.3 | C17—C16—H16 | 120.1 |
C8—C7—H7B | 110.3 | C16—C17—C12 | 121.26 (14) |
H7A—C7—H7B | 108.5 | C16—C17—H17 | 119.4 |
C11—C8—C9 | 120.33 (12) | C12—C17—H17 | 119.4 |
C11—C8—C7 | 124.35 (13) | O4—N1—O3 | 123.64 (13) |
C9—C8—C7 | 115.26 (13) | O4—N1—C4 | 117.88 (15) |
O2—C9—C8 | 120.24 (14) | O3—N1—C4 | 118.49 (13) |
O2—C9—C10 | 120.09 (14) | O6—N2—O5 | 124.41 (13) |
C8—C9—C10 | 119.67 (14) | O6—N2—C2 | 118.65 (12) |
C9—C10—H10A | 109.5 | O5—N2—C2 | 116.90 (12) |
C9—C10—H10B | 109.5 | C1—O1—C7 | 117.86 (10) |
O1—C1—C2—C3 | 173.75 (11) | C8—C11—C12—C17 | −150.23 (16) |
C6—C1—C2—C3 | −3.9 (2) | C8—C11—C12—C13 | 33.5 (2) |
O1—C1—C2—N2 | −5.24 (18) | C17—C12—C13—C14 | 1.2 (2) |
C6—C1—C2—N2 | 177.08 (12) | C11—C12—C13—C14 | 177.53 (15) |
C1—C2—C3—C4 | 3.50 (19) | C12—C13—C14—C15 | −0.2 (3) |
N2—C2—C3—C4 | −177.48 (11) | C13—C14—C15—C16 | −0.4 (3) |
C2—C3—C4—C5 | −0.6 (2) | C14—C15—C16—C17 | −0.1 (3) |
C2—C3—C4—N1 | 179.98 (11) | C15—C16—C17—C12 | 1.1 (3) |
C3—C4—C5—C6 | −1.8 (2) | C13—C12—C17—C16 | −1.7 (2) |
N1—C4—C5—C6 | 177.66 (13) | C11—C12—C17—C16 | −178.17 (15) |
C4—C5—C6—C1 | 1.3 (2) | C3—C4—N1—O4 | −176.08 (13) |
O1—C1—C6—C5 | −176.05 (13) | C5—C4—N1—O4 | 4.5 (2) |
C2—C1—C6—C5 | 1.5 (2) | C3—C4—N1—O3 | 4.2 (2) |
O1—C7—C8—C11 | −94.16 (16) | C5—C4—N1—O3 | −175.29 (14) |
O1—C7—C8—C9 | 88.75 (14) | C3—C2—N2—O6 | 137.34 (13) |
C11—C8—C9—O2 | −171.36 (15) | C1—C2—N2—O6 | −43.62 (17) |
C7—C8—C9—O2 | 5.9 (2) | C3—C2—N2—O5 | −40.76 (17) |
C11—C8—C9—C10 | 9.5 (2) | C1—C2—N2—O5 | 138.28 (13) |
C7—C8—C9—C10 | −173.26 (13) | C6—C1—O1—C7 | 5.4 (2) |
C9—C8—C11—C12 | −178.44 (14) | C2—C1—O1—C7 | −172.16 (12) |
C7—C8—C11—C12 | 4.6 (2) | C8—C7—O1—C1 | 178.57 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O5i | 0.93 | 2.41 | 3.1375 (18) | 135 |
C16—H16···O6ii | 0.93 | 2.58 | 3.292 (3) | 134 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O5i | 0.93 | 2.41 | 3.1375 (18) | 135 |
C16—H16···O6ii | 0.93 | 2.58 | 3.292 (3) | 134 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y+1/2, −z+1/2. |
Acknowledgements
We thank Professor Regina H. A. Santos from IQSC–USP for the data collection. The Brazilian agencies CNPq (306121/2013-1 to IC), CAPES (808/2009 to IC) and FAPESP (2012/22524-9 to SHM) are acknowledged for financial support.
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