organic compounds
2,2-Dimethyl-5-(2-nitrobenzylidene)-1,3-dioxane-4,6-dione
aCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico, and bDivisión Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, AP 24, 86690, Cuanduacán Tab., Mexico
*Correspondence e-mail: angel.mendoza.m@gmail.com
The 13H11NO6, contains two molecules in both of which the six-membered 1,3-dioxane-4,6-dione ring shows a screw-boat conformation. The dihedral angles between the best planes through the six-membered rings are 47.8 (2) and 49.8 (2)°. In the crystal, C—H⋯O interactions link the molecules, building a supramolecular sheet parallel to the c axis.
of the title compound, CRelated literature
For general applications of Meldrum's acid, see: Palasz et al. (2007); Fillion et al. (2006); Mizukami et al. (1993). For the synthesis of see: Scott & Raston (2000); Alvim et al. (2005); Fillion & Dumas (2008). For combinatorial synthesis, see: Shaabani et al. (2004); Wang et al. (2007); Cochard et al. (2004). For puckering parameters, see: Cremer & Pople (1975). For NMR data, see: Bigi et al. (2001).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812049677/bt6875sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049677/bt6875Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049677/bt6875Isup3.cml
In a balloon flask was placed 0.33 mmol of 2-nitrobenzaldehyde, 1 eq. of Meldrum's acid and 3 ml of water. The mixture was subjected to ultrasonic radiation for 37 min. The reaction product was isolated from the aqueous medium by ν max/cm-1 (neat KBr) 2925, 1737, 1640, 1600, 1525, 1350, 1380, 1290, 1200, and 725. 1H NMR (400 MHz, CDCl3): δ (p.p.m.) = 8.80 (s, 1H); 8.3 (dd, 1H); 7.77 (t, 1H); 7.6(t, 1H); 7.5(d, 1H); 1.8 (s, 6H). 13C NMR data are in good agreement with those described in the literature (Bigi et al., 2001)
3 x 10 ml. CH2Cl2 and the crude product recrystallized from CH2Cl2/Et2O (1:1) to give (I) in 72% yield. m.p 117°C. For ultrasonic radiation we employed an ultrasonic bath Cole-Parmer 08890–21. All chemicals were purchased from Sigma-Aldrich. Spectroscopic analysis:H atoms were placed in geometrical idealized positions and refined as riding on their parent atoms, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(methyl C).
The 5-arylidenes Meldrum's acid derivatives, like title compound, are versatile intermediates in organic synthesis, for example, this type of compounds were used in hetero-Diels-Alder reaction (Palasz et al. 2007; Fillion et al. 2006 and Mizukami et al. 1993), as well as in the synthesis of heterocycle compound, like γ-Butyrolactones and pyrrole derivatives (Fillion et al. 2008). Also, the 5-arylidene derivatives of Meldrum's acid possess an α, β-unsaturated carbonyl system, which is considered as a key building block in combinatorial reaction for three components synthesis (Shaabani et al. 2004 and Wang et al. 2007), alike four components reaction (Cochard et al. 2004). The title compound was obtained by a green Knoevenagel condensation of Meldrum acid with 2-nitrobenzaldehyde employing ultrasonic radiation and water as solvent.
(Scott et al. 2000 and Alvim et al. 2005);In the title compound C13 H11 N O6, the ASU contains two molecules showing a 2,2-dimethyl-1,3-dioxane-4,6-dione group opposite to o-nitrophenyl ring for each molecule. The 1,3-dioxane ring shows a screw-boat conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.4807 (14) Å, θ2 = 73.12° (17), φ2 = 300.32° (17), q2 = 0.4600 (14) Å and q3 = 0.1396 (14) Å for the six member ring O3/C5/C4/C7/O4/C6 and Q = 0.5031 (14) Å, θ2 = 103.03 (16)°, φ2 = 121.91 (16)°, q2 = 0.4901 (14) Å and q3 = -0.1135 (14) Å for the six member ring O9/C18/C17/C20/O10/C19. The C=O groups and carbon atom between them show a maximun deviation from mean plane of 0.256 Å for molecule 1 and 0.311 Å for molecule 2. The dihedral angle for p-nitrophenyl rings and C=C bond are 56.1 (2)° for molecule 1 (C2/C3/C4/C10) and 60.5 (2)° for molecule 2 (C15/C16/C17/C23). The crystal packing present six intermolecular interactions of the type C—H···O hydrogen bonds (table 1).
For general applications of Meldrum's acid, see: Palasz et al. (2007); Fillion et al. (2006); Mizukami et al. (1993). For the synthesis of
see: Scott & Raston (2000); Alvim et al. (2005); Fillion & Dumas (2008). For combinatorial synthesis, see: Shaabani et al. (2004); Wang et al. (2007); Cochard et al. (2004). For puckering parameters, see: Cremer & Pople (1975). For NMR data, see: Bigi et al. (2001).Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure of title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. |
C13H11NO6 | Z = 4 |
Mr = 277.23 | F(000) = 576 |
Triclinic, P1 | Dx = 1.474 Mg m−3 |
a = 10.0240 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4830 (5) Å | Cell parameters from 5470 reflections |
c = 12.4076 (5) Å | θ = 3.4–25.2° |
α = 105.385 (4)° | µ = 0.12 mm−1 |
β = 94.669 (3)° | T = 130 K |
γ = 93.096 (3)° | Prism, colorless |
V = 1249.03 (10) Å3 | 0.39 × 0.22 × 0.14 mm |
Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer | 4526 independent reflections |
Graphite monochromator | 3902 reflections with I > 2σ(I) |
Detector resolution: 10.4685 pixels mm-1 | Rint = 0.018 |
ω scans | θmax = 25.3°, θmin = 3.4° |
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009) | h = −12→12 |
Tmin = 0.968, Tmax = 0.985 | k = −10→12 |
8703 measured reflections | l = −13→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.3347P] where P = (Fo2 + 2Fc2)/3 |
4526 reflections | (Δ/σ)max < 0.001 |
365 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C13H11NO6 | γ = 93.096 (3)° |
Mr = 277.23 | V = 1249.03 (10) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.0240 (4) Å | Mo Kα radiation |
b = 10.4830 (5) Å | µ = 0.12 mm−1 |
c = 12.4076 (5) Å | T = 130 K |
α = 105.385 (4)° | 0.39 × 0.22 × 0.14 mm |
β = 94.669 (3)° |
Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer | 4526 independent reflections |
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009) | 3902 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.985 | Rint = 0.018 |
8703 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.22 e Å−3 |
4526 reflections | Δρmin = −0.24 e Å−3 |
365 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 | ||
O1 | 0.61144 (10) | 0.10481 (11) | 0.54216 (9) | 0.0347 (3) | |
O2 | 0.53572 (11) | 0.09437 (10) | 0.69780 (9) | 0.0351 (3) | |
O6 | 0.23911 (10) | 0.16149 (11) | 0.32752 (8) | 0.0334 (3) | |
O5 | 0.68803 (9) | 0.16562 (11) | 0.25320 (8) | 0.0293 (2) | |
O3 | 0.29864 (9) | 0.16222 (10) | 0.16040 (8) | 0.0260 (2) | |
O4 | 0.52511 (9) | 0.16412 (10) | 0.12250 (8) | 0.0255 (2) | |
N1 | 0.54108 (11) | 0.14413 (11) | 0.61912 (10) | 0.0241 (3) | |
C2 | 0.44468 (13) | 0.30112 (13) | 0.52086 (11) | 0.0203 (3) | |
C1 | 0.46117 (13) | 0.25651 (13) | 0.61755 (11) | 0.0203 (3) | |
C13 | 0.40048 (14) | 0.31165 (14) | 0.71352 (11) | 0.0240 (3) | |
H8 | 0.4137 | 0.2793 | 0.7762 | 0.029* | |
C12 | 0.32022 (14) | 0.41500 (14) | 0.71558 (12) | 0.0264 (3) | |
H9 | 0.2803 | 0.4543 | 0.7801 | 0.032* | |
C11 | 0.29991 (14) | 0.45936 (14) | 0.62034 (12) | 0.0263 (3) | |
H10 | 0.2446 | 0.5279 | 0.6207 | 0.032* | |
C10 | 0.36058 (13) | 0.40341 (14) | 0.52468 (12) | 0.0243 (3) | |
H11 | 0.345 | 0.4347 | 0.4616 | 0.029* | |
C3 | 0.51994 (13) | 0.25533 (13) | 0.42226 (11) | 0.0215 (3) | |
H7 | 0.6126 | 0.2577 | 0.4371 | 0.026* | |
C4 | 0.47179 (13) | 0.21081 (13) | 0.31422 (11) | 0.0209 (3) | |
C5 | 0.32781 (14) | 0.17904 (14) | 0.27213 (12) | 0.0241 (3) | |
C7 | 0.57212 (13) | 0.18052 (14) | 0.23029 (11) | 0.0222 (3) | |
C6 | 0.39619 (13) | 0.21135 (15) | 0.09837 (12) | 0.0243 (3) | |
C8 | 0.35526 (15) | 0.14531 (17) | −0.02350 (12) | 0.0330 (4) | |
H1 | 0.2719 | 0.1764 | −0.0458 | 0.05* | |
H2 | 0.3444 | 0.0509 | −0.0351 | 0.05* | |
H3 | 0.4233 | 0.1663 | −0.0676 | 0.05* | |
C9 | 0.40534 (15) | 0.36051 (15) | 0.12822 (13) | 0.0302 (3) | |
H4 | 0.3197 | 0.3899 | 0.1091 | 0.045* | |
H5 | 0.4716 | 0.3912 | 0.0872 | 0.045* | |
H6 | 0.4306 | 0.3957 | 0.2074 | 0.045* | |
O7 | 0.21049 (10) | 0.63351 (11) | 0.34639 (9) | 0.0367 (3) | |
O8 | 0.12315 (15) | 0.64061 (17) | 0.49838 (11) | 0.0703 (5) | |
O11 | −0.11562 (10) | 0.62735 (10) | 0.09585 (9) | 0.0305 (2) | |
O12 | 0.33877 (10) | 0.68213 (12) | 0.06066 (9) | 0.0380 (3) | |
O10 | −0.04438 (9) | 0.64388 (9) | −0.06351 (8) | 0.0235 (2) | |
O9 | 0.18763 (9) | 0.66645 (9) | −0.08312 (8) | 0.0230 (2) | |
N2 | 0.12876 (12) | 0.67424 (13) | 0.41284 (10) | 0.0297 (3) | |
C15 | 0.04065 (13) | 0.81061 (14) | 0.29236 (11) | 0.0236 (3) | |
C23 | −0.05066 (14) | 0.90041 (15) | 0.27642 (12) | 0.0282 (3) | |
H22 | −0.0497 | 0.9318 | 0.2131 | 0.034* | |
C24 | −0.14323 (14) | 0.94452 (15) | 0.35226 (13) | 0.0291 (3) | |
H21 | −0.2031 | 1.0049 | 0.3395 | 0.035* | |
C25 | −0.14677 (14) | 0.89901 (14) | 0.44700 (12) | 0.0267 (3) | |
H20 | −0.2091 | 0.9285 | 0.4978 | 0.032* | |
C26 | −0.05768 (14) | 0.80991 (14) | 0.46575 (11) | 0.0246 (3) | |
H19 | −0.0596 | 0.7782 | 0.5289 | 0.029* | |
C14 | 0.03491 (13) | 0.76803 (13) | 0.38935 (11) | 0.0218 (3) | |
C16 | 0.14020 (14) | 0.77088 (15) | 0.21051 (12) | 0.0263 (3) | |
H18 | 0.2304 | 0.7894 | 0.2375 | 0.032* | |
C17 | 0.11190 (13) | 0.71080 (14) | 0.10134 (12) | 0.0232 (3) | |
C18 | 0.22400 (14) | 0.68726 (14) | 0.02790 (12) | 0.0256 (3) | |
C20 | −0.02527 (13) | 0.65966 (13) | 0.04834 (11) | 0.0220 (3) | |
C19 | 0.05674 (13) | 0.70168 (14) | −0.11726 (11) | 0.0223 (3) | |
C21 | 0.05316 (14) | 0.85027 (14) | −0.08805 (12) | 0.0265 (3) | |
H12 | −0.0339 | 0.8722 | −0.1125 | 0.04* | |
H13 | 0.1202 | 0.8868 | −0.1249 | 0.04* | |
H14 | 0.0709 | 0.8865 | −0.0082 | 0.04* | |
C22 | 0.02837 (15) | 0.63545 (16) | −0.24028 (12) | 0.0321 (4) | |
H15 | −0.0618 | 0.6486 | −0.2651 | 0.048* | |
H16 | 0.0385 | 0.5421 | −0.2539 | 0.048* | |
H17 | 0.0902 | 0.6731 | −0.2808 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0352 (6) | 0.0324 (6) | 0.0391 (6) | 0.0151 (5) | 0.0113 (5) | 0.0096 (5) |
O2 | 0.0461 (7) | 0.0304 (6) | 0.0325 (6) | 0.0077 (5) | −0.0012 (5) | 0.0158 (5) |
O6 | 0.0196 (5) | 0.0511 (7) | 0.0312 (6) | 0.0000 (5) | 0.0079 (4) | 0.0131 (5) |
O5 | 0.0189 (5) | 0.0423 (6) | 0.0304 (6) | 0.0084 (5) | 0.0056 (4) | 0.0143 (5) |
O3 | 0.0199 (5) | 0.0345 (6) | 0.0234 (5) | −0.0002 (4) | 0.0016 (4) | 0.0084 (4) |
O4 | 0.0213 (5) | 0.0358 (6) | 0.0218 (5) | 0.0085 (4) | 0.0049 (4) | 0.0097 (4) |
N1 | 0.0233 (6) | 0.0215 (6) | 0.0259 (7) | 0.0011 (5) | −0.0038 (5) | 0.0056 (5) |
C2 | 0.0161 (6) | 0.0212 (7) | 0.0232 (7) | −0.0007 (5) | 0.0007 (5) | 0.0059 (6) |
C1 | 0.0171 (7) | 0.0173 (7) | 0.0252 (7) | −0.0004 (5) | −0.0016 (5) | 0.0050 (5) |
C13 | 0.0264 (7) | 0.0248 (7) | 0.0208 (7) | −0.0013 (6) | 0.0008 (6) | 0.0072 (6) |
C12 | 0.0267 (8) | 0.0246 (7) | 0.0262 (8) | 0.0015 (6) | 0.0084 (6) | 0.0026 (6) |
C11 | 0.0238 (7) | 0.0232 (7) | 0.0332 (8) | 0.0067 (6) | 0.0070 (6) | 0.0075 (6) |
C10 | 0.0226 (7) | 0.0270 (8) | 0.0264 (8) | 0.0038 (6) | 0.0034 (6) | 0.0121 (6) |
C3 | 0.0171 (7) | 0.0225 (7) | 0.0274 (8) | 0.0032 (6) | 0.0035 (5) | 0.0105 (6) |
C4 | 0.0188 (7) | 0.0222 (7) | 0.0244 (7) | 0.0039 (6) | 0.0047 (5) | 0.0098 (6) |
C5 | 0.0212 (7) | 0.0260 (8) | 0.0259 (8) | 0.0044 (6) | 0.0037 (6) | 0.0076 (6) |
C7 | 0.0219 (7) | 0.0232 (7) | 0.0231 (7) | 0.0028 (6) | 0.0042 (6) | 0.0084 (6) |
C6 | 0.0164 (7) | 0.0332 (8) | 0.0259 (8) | 0.0042 (6) | 0.0038 (5) | 0.0116 (6) |
C8 | 0.0300 (8) | 0.0439 (10) | 0.0249 (8) | 0.0053 (7) | 0.0005 (6) | 0.0091 (7) |
C9 | 0.0273 (8) | 0.0311 (8) | 0.0343 (9) | 0.0036 (7) | 0.0014 (6) | 0.0126 (7) |
O7 | 0.0308 (6) | 0.0402 (7) | 0.0411 (7) | 0.0121 (5) | 0.0056 (5) | 0.0124 (5) |
O8 | 0.0808 (10) | 0.1092 (13) | 0.0500 (9) | 0.0550 (10) | 0.0230 (7) | 0.0579 (9) |
O11 | 0.0240 (5) | 0.0348 (6) | 0.0374 (6) | −0.0012 (5) | 0.0082 (4) | 0.0173 (5) |
O12 | 0.0183 (5) | 0.0609 (8) | 0.0386 (6) | 0.0095 (5) | 0.0038 (4) | 0.0185 (6) |
O10 | 0.0185 (5) | 0.0263 (5) | 0.0243 (5) | −0.0002 (4) | 0.0039 (4) | 0.0045 (4) |
O9 | 0.0186 (5) | 0.0264 (5) | 0.0246 (5) | 0.0066 (4) | 0.0055 (4) | 0.0061 (4) |
N2 | 0.0281 (7) | 0.0360 (7) | 0.0262 (7) | 0.0032 (6) | −0.0032 (5) | 0.0120 (6) |
C15 | 0.0199 (7) | 0.0275 (8) | 0.0230 (7) | −0.0015 (6) | −0.0011 (5) | 0.0077 (6) |
C23 | 0.0289 (8) | 0.0315 (8) | 0.0282 (8) | 0.0021 (6) | 0.0000 (6) | 0.0158 (6) |
C24 | 0.0250 (8) | 0.0255 (8) | 0.0363 (9) | 0.0039 (6) | −0.0005 (6) | 0.0080 (6) |
C25 | 0.0214 (7) | 0.0265 (8) | 0.0289 (8) | −0.0022 (6) | 0.0031 (6) | 0.0023 (6) |
C26 | 0.0245 (7) | 0.0282 (8) | 0.0202 (7) | −0.0054 (6) | −0.0004 (5) | 0.0074 (6) |
C14 | 0.0192 (7) | 0.0234 (7) | 0.0220 (7) | −0.0007 (6) | −0.0044 (5) | 0.0069 (6) |
C16 | 0.0203 (7) | 0.0346 (8) | 0.0275 (8) | 0.0028 (6) | 0.0009 (6) | 0.0149 (6) |
C17 | 0.0190 (7) | 0.0266 (7) | 0.0279 (8) | 0.0044 (6) | 0.0049 (6) | 0.0131 (6) |
C18 | 0.0215 (8) | 0.0282 (8) | 0.0293 (8) | 0.0037 (6) | 0.0048 (6) | 0.0103 (6) |
C20 | 0.0217 (7) | 0.0189 (7) | 0.0276 (8) | 0.0058 (6) | 0.0051 (6) | 0.0084 (6) |
C19 | 0.0163 (7) | 0.0279 (8) | 0.0239 (7) | 0.0040 (6) | 0.0054 (5) | 0.0078 (6) |
C21 | 0.0263 (8) | 0.0278 (8) | 0.0285 (8) | 0.0071 (6) | 0.0073 (6) | 0.0106 (6) |
C22 | 0.0259 (8) | 0.0423 (9) | 0.0253 (8) | 0.0048 (7) | 0.0044 (6) | 0.0031 (7) |
O1—N1 | 1.2293 (15) | O7—N2 | 1.2223 (15) |
O2—N1 | 1.2263 (15) | O8—N2 | 1.2083 (16) |
O6—C5 | 1.2024 (16) | O11—C20 | 1.2009 (16) |
O5—C7 | 1.2018 (16) | O12—C18 | 1.1974 (17) |
O3—C5 | 1.3554 (17) | O10—C20 | 1.3497 (16) |
O3—C6 | 1.4464 (16) | O10—C19 | 1.4482 (16) |
O4—C7 | 1.3442 (16) | O9—C18 | 1.3521 (17) |
O4—C6 | 1.4455 (16) | O9—C19 | 1.4430 (16) |
N1—C1 | 1.4634 (17) | N2—C14 | 1.4642 (18) |
C2—C10 | 1.3928 (19) | C15—C23 | 1.388 (2) |
C2—C1 | 1.3996 (19) | C15—C14 | 1.3944 (19) |
C2—C3 | 1.4745 (18) | C15—C16 | 1.4785 (19) |
C1—C13 | 1.3830 (19) | C23—C24 | 1.385 (2) |
C13—C12 | 1.380 (2) | C23—H22 | 0.93 |
C13—H8 | 0.93 | C24—C25 | 1.383 (2) |
C12—C11 | 1.385 (2) | C24—H21 | 0.93 |
C12—H9 | 0.93 | C25—C26 | 1.377 (2) |
C11—C10 | 1.3818 (19) | C25—H20 | 0.93 |
C11—H10 | 0.93 | C26—C14 | 1.3853 (19) |
C10—H11 | 0.93 | C26—H19 | 0.93 |
C3—C4 | 1.3364 (19) | C16—C17 | 1.333 (2) |
C3—H7 | 0.93 | C16—H18 | 0.93 |
C4—C5 | 1.4831 (19) | C17—C20 | 1.4820 (19) |
C4—C7 | 1.4921 (18) | C17—C18 | 1.4938 (19) |
C6—C8 | 1.499 (2) | C19—C22 | 1.4961 (19) |
C6—C9 | 1.504 (2) | C19—C21 | 1.506 (2) |
C8—H1 | 0.96 | C21—H12 | 0.96 |
C8—H2 | 0.96 | C21—H13 | 0.96 |
C8—H3 | 0.96 | C21—H14 | 0.96 |
C9—H4 | 0.96 | C22—H15 | 0.96 |
C9—H5 | 0.96 | C22—H16 | 0.96 |
C9—H6 | 0.96 | C22—H17 | 0.96 |
C5—O3—C6 | 119.09 (10) | C20—O10—C19 | 118.89 (10) |
C7—O4—C6 | 118.75 (10) | C18—O9—C19 | 118.26 (10) |
O2—N1—O1 | 123.04 (12) | O8—N2—O7 | 122.23 (13) |
O2—N1—C1 | 118.41 (11) | O8—N2—C14 | 118.42 (12) |
O1—N1—C1 | 118.54 (11) | O7—N2—C14 | 119.35 (12) |
C10—C2—C1 | 116.46 (12) | C23—C15—C14 | 116.39 (13) |
C10—C2—C3 | 119.36 (12) | C23—C15—C16 | 119.29 (12) |
C1—C2—C3 | 123.91 (12) | C14—C15—C16 | 124.26 (13) |
C13—C1—C2 | 122.65 (12) | C24—C23—C15 | 121.82 (13) |
C13—C1—N1 | 116.92 (12) | C24—C23—H22 | 119.1 |
C2—C1—N1 | 120.40 (12) | C15—C23—H22 | 119.1 |
C12—C13—C1 | 119.50 (13) | C25—C24—C23 | 120.14 (14) |
C12—C13—H8 | 120.3 | C25—C24—H21 | 119.9 |
C1—C13—H8 | 120.3 | C23—C24—H21 | 119.9 |
C13—C12—C11 | 119.10 (13) | C26—C25—C24 | 119.73 (13) |
C13—C12—H9 | 120.5 | C26—C25—H20 | 120.1 |
C11—C12—H9 | 120.5 | C24—C25—H20 | 120.1 |
C10—C11—C12 | 121.01 (13) | C25—C26—C14 | 119.18 (13) |
C10—C11—H10 | 119.5 | C25—C26—H19 | 120.4 |
C12—C11—H10 | 119.5 | C14—C26—H19 | 120.4 |
C11—C10—C2 | 121.25 (13) | C26—C14—C15 | 122.73 (13) |
C11—C10—H11 | 119.4 | C26—C14—N2 | 117.53 (12) |
C2—C10—H11 | 119.4 | C15—C14—N2 | 119.74 (12) |
C4—C3—C2 | 128.19 (12) | C17—C16—C15 | 125.68 (13) |
C4—C3—H7 | 115.9 | C17—C16—H18 | 117.2 |
C2—C3—H7 | 115.9 | C15—C16—H18 | 117.2 |
C3—C4—C5 | 125.32 (12) | C16—C17—C20 | 123.63 (12) |
C3—C4—C7 | 116.92 (12) | C16—C17—C18 | 119.06 (12) |
C5—C4—C7 | 117.57 (12) | C20—C17—C18 | 117.25 (12) |
O6—C5—O3 | 119.04 (12) | O12—C18—O9 | 120.03 (12) |
O6—C5—C4 | 125.42 (13) | O12—C18—C17 | 124.61 (13) |
O3—C5—C4 | 115.44 (11) | O9—C18—C17 | 115.32 (11) |
O5—C7—O4 | 119.64 (12) | O11—C20—O10 | 119.26 (12) |
O5—C7—C4 | 124.14 (12) | O11—C20—C17 | 125.36 (13) |
O4—C7—C4 | 116.15 (11) | O10—C20—C17 | 115.31 (11) |
O4—C6—O3 | 109.08 (10) | O9—C19—O10 | 109.68 (10) |
O4—C6—C8 | 105.46 (11) | O9—C19—C22 | 106.65 (11) |
O3—C6—C8 | 106.45 (11) | O10—C19—C22 | 105.78 (11) |
O4—C6—C9 | 110.69 (11) | O9—C19—C21 | 110.39 (11) |
O3—C6—C9 | 110.72 (11) | O10—C19—C21 | 110.60 (11) |
C8—C6—C9 | 114.17 (12) | C22—C19—C21 | 113.56 (12) |
C6—C8—H1 | 109.5 | C19—C21—H12 | 109.5 |
C6—C8—H2 | 109.5 | C19—C21—H13 | 109.5 |
H1—C8—H2 | 109.5 | H12—C21—H13 | 109.5 |
C6—C8—H3 | 109.5 | C19—C21—H14 | 109.5 |
H1—C8—H3 | 109.5 | H12—C21—H14 | 109.5 |
H2—C8—H3 | 109.5 | H13—C21—H14 | 109.5 |
C6—C9—H4 | 109.5 | C19—C22—H15 | 109.5 |
C6—C9—H5 | 109.5 | C19—C22—H16 | 109.5 |
H4—C9—H5 | 109.5 | H15—C22—H16 | 109.5 |
C6—C9—H6 | 109.5 | C19—C22—H17 | 109.5 |
H4—C9—H6 | 109.5 | H15—C22—H17 | 109.5 |
H5—C9—H6 | 109.5 | H16—C22—H17 | 109.5 |
C10—C2—C1—C13 | −1.4 (2) | C14—C15—C23—C24 | −0.5 (2) |
C3—C2—C1—C13 | 172.63 (13) | C16—C15—C23—C24 | −177.84 (13) |
C10—C2—C1—N1 | 176.31 (11) | C15—C23—C24—C25 | −0.1 (2) |
C3—C2—C1—N1 | −9.7 (2) | C23—C24—C25—C26 | 0.2 (2) |
O2—N1—C1—C13 | 9.41 (18) | C24—C25—C26—C14 | 0.4 (2) |
O1—N1—C1—C13 | −169.89 (12) | C25—C26—C14—C15 | −1.1 (2) |
O2—N1—C1—C2 | −168.41 (12) | C25—C26—C14—N2 | 179.42 (12) |
O1—N1—C1—C2 | 12.29 (18) | C23—C15—C14—C26 | 1.2 (2) |
C2—C1—C13—C12 | −0.1 (2) | C16—C15—C14—C26 | 178.33 (13) |
N1—C1—C13—C12 | −177.85 (12) | C23—C15—C14—N2 | −179.42 (12) |
C1—C13—C12—C11 | 1.4 (2) | C16—C15—C14—N2 | −2.2 (2) |
C13—C12—C11—C10 | −1.2 (2) | O8—N2—C14—C26 | −1.8 (2) |
C12—C11—C10—C2 | −0.3 (2) | O7—N2—C14—C26 | 178.86 (13) |
C1—C2—C10—C11 | 1.6 (2) | O8—N2—C14—C15 | 178.79 (15) |
C3—C2—C10—C11 | −172.72 (13) | O7—N2—C14—C15 | −0.60 (19) |
C10—C2—C3—C4 | −56.1 (2) | C23—C15—C16—C17 | −60.5 (2) |
C1—C2—C3—C4 | 130.06 (16) | C14—C15—C16—C17 | 122.41 (16) |
C2—C3—C4—C5 | −9.8 (2) | C15—C16—C17—C20 | −7.9 (2) |
C2—C3—C4—C7 | 175.41 (13) | C15—C16—C17—C18 | 174.98 (13) |
C6—O3—C5—O6 | 166.16 (13) | C19—O9—C18—O12 | −166.58 (13) |
C6—O3—C5—C4 | −17.28 (17) | C19—O9—C18—C17 | 15.59 (17) |
C3—C4—C5—O6 | −16.9 (2) | C16—C17—C18—O12 | 22.6 (2) |
C7—C4—C5—O6 | 157.82 (14) | C20—C17—C18—O12 | −154.70 (14) |
C3—C4—C5—O3 | 166.76 (13) | C16—C17—C18—O9 | −159.71 (13) |
C7—C4—C5—O3 | −18.49 (18) | C20—C17—C18—O9 | 23.02 (18) |
C6—O4—C7—O5 | −165.93 (13) | C19—O10—C20—O11 | 170.43 (12) |
C6—O4—C7—C4 | 16.79 (17) | C19—O10—C20—C17 | −12.53 (17) |
C3—C4—C7—O5 | 16.9 (2) | C16—C17—C20—O11 | −24.8 (2) |
C5—C4—C7—O5 | −158.32 (14) | C18—C17—C20—O11 | 152.33 (14) |
C3—C4—C7—O4 | −165.97 (12) | C16—C17—C20—O10 | 158.34 (13) |
C5—C4—C7—O4 | 18.83 (18) | C18—C17—C20—O10 | −24.51 (17) |
C7—O4—C6—O3 | −50.14 (15) | C18—O9—C19—O10 | −50.65 (15) |
C7—O4—C6—C8 | −164.12 (12) | C18—O9—C19—C22 | −164.75 (12) |
C7—O4—C6—C9 | 71.93 (15) | C18—O9—C19—C21 | 71.46 (14) |
C5—O3—C6—O4 | 50.57 (15) | C20—O10—C19—O9 | 49.17 (15) |
C5—O3—C6—C8 | 163.91 (12) | C20—O10—C19—C22 | 163.83 (11) |
C5—O3—C6—C9 | −71.47 (15) | C20—O10—C19—C21 | −72.81 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H7···O5 | 0.93 | 2.43 | 2.7970 (16) | 104 |
C11—H10···O8 | 0.93 | 2.45 | 3.239 (2) | 143 |
C21—H13···O5i | 0.96 | 2.58 | 3.4188 (17) | 145 |
C16—H18···O12 | 0.93 | 2.54 | 2.8582 (18) | 100 |
C16—H18···O2ii | 0.93 | 2.55 | 3.4486 (18) | 163 |
C24—H21···O5iii | 0.93 | 2.48 | 3.3676 (19) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C13H11NO6 |
Mr | 277.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 130 |
a, b, c (Å) | 10.0240 (4), 10.4830 (5), 12.4076 (5) |
α, β, γ (°) | 105.385 (4), 94.669 (3), 93.096 (3) |
V (Å3) | 1249.03 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.39 × 0.22 × 0.14 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Atlas, Gemini) |
Absorption correction | Analytical (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.968, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8703, 4526, 3902 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.088, 1.03 |
No. of reflections | 4526 |
No. of parameters | 365 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.24 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H7···O5 | 0.93 | 2.43 | 2.7970 (16) | 104 |
C11—H10···O8 | 0.93 | 2.45 | 3.239 (2) | 143 |
C21—H13···O5i | 0.96 | 2.58 | 3.4188 (17) | 145 |
C16—H18···O12 | 0.93 | 2.54 | 2.8582 (18) | 100 |
C16—H18···O2ii | 0.93 | 2.55 | 3.4486 (18) | 163 |
C24—H21···O5iii | 0.93 | 2.48 | 3.3676 (19) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y+1, z. |
Acknowledgements
The authors acknowledge the Universidad Juárez Autónoma de Tabasco for financial support via projects UJAT-2009-C05–02 and UJAT-2011-C07–22
References
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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 5-arylidenes Meldrum's acid derivatives, like title compound, are versatile intermediates in organic synthesis, for example, this type of compounds were used in hetero-Diels-Alder reaction (Palasz et al. 2007; Fillion et al. 2006 and Mizukami et al. 1993), as well as in the synthesis of heterocycle compound, like coumarins (Scott et al. 2000 and Alvim et al. 2005); γ-Butyrolactones and pyrrole derivatives (Fillion et al. 2008). Also, the 5-arylidene derivatives of Meldrum's acid possess an α, β-unsaturated carbonyl system, which is considered as a key building block in combinatorial reaction for three components synthesis (Shaabani et al. 2004 and Wang et al. 2007), alike four components reaction (Cochard et al. 2004). The title compound was obtained by a green Knoevenagel condensation of Meldrum acid with 2-nitrobenzaldehyde employing ultrasonic radiation and water as solvent.
In the title compound C13 H11 N O6, the ASU contains two molecules showing a 2,2-dimethyl-1,3-dioxane-4,6-dione group opposite to o-nitrophenyl ring for each molecule. The 1,3-dioxane ring shows a screw-boat conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.4807 (14) Å, θ2 = 73.12° (17), φ2 = 300.32° (17), q2 = 0.4600 (14) Å and q3 = 0.1396 (14) Å for the six member ring O3/C5/C4/C7/O4/C6 and Q = 0.5031 (14) Å, θ2 = 103.03 (16)°, φ2 = 121.91 (16)°, q2 = 0.4901 (14) Å and q3 = -0.1135 (14) Å for the six member ring O9/C18/C17/C20/O10/C19. The C=O groups and carbon atom between them show a maximun deviation from mean plane of 0.256 Å for molecule 1 and 0.311 Å for molecule 2. The dihedral angle for p-nitrophenyl rings and C=C bond are 56.1 (2)° for molecule 1 (C2/C3/C4/C10) and 60.5 (2)° for molecule 2 (C15/C16/C17/C23). The crystal packing present six intermolecular interactions of the type C—H···O hydrogen bonds (table 1).