2,2-Dimethyl-5-(2-nitro­benzyl­idene)-1,3-dioxane-4,6-dione

García-Álvarez, F.; Romero, N.; Lobato-García, C.E.; Terán, J.L.; Mendoza, A.

doi:10.1107/S1600536812049677

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o50

https://doi.org/10.1107/S1600536812049677

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2,2-Dimethyl-5-(2-nitrobenzylidene)-1,3-dioxane-4,6-dione

Fernando García-Álvarez,^a Nancy Romero,^b Carlos E. Lobato-García,^b Joel L. Terán ^a and Angel Mendoza ^a ^*

^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

(Received 28 November 2012; accepted 3 December 2012; online 8 December 2012)

The asymmetric unit of the title compound, C₁₃H₁₁NO₆, 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.

Related 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 heterocyclic compounds, 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

C₁₃H₁₁NO₆
M_r = 277.23
Triclinic, $[P \overline 1]$
a = 10.0240 (4) Å
b = 10.4830 (5) Å
c = 12.4076 (5) Å
α = 105.385 (4)°
β = 94.669 (3)°
γ = 93.096 (3)°
V = 1249.03 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 130 K
0.39 × 0.22 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.968, T_max = 0.985
8703 measured reflections
4526 independent reflections
3902 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.03
4526 reflections
365 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812049677/bt6875sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

For general applications of Meldrum's acid, see: Palasz et al. (2007); Fillion et al. (2006); Mizukami et al. (1993). For the synthesis of heterocyclic compounds, 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 top

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 liquid-liquid extraction 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: 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)

Structure description top

For general applications of Meldrum's acid, see: Palasz et al. (2007); Fillion et al. (2006); Mizukami et al. (1993). For the synthesis of heterocyclic compounds, 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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: 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).

Figures top

Fig. 1. The molecular structure of title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

2,2-Dimethyl-5-(2-nitrobenzylidene)-1,3-dioxane-4,6-dione top

Crystal data top

C₁₃H₁₁NO₆	Z = 4
M_r = 277.23	F(000) = 576
Triclinic, P1	D_x = 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

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	4526 independent reflections
Graphite monochromator	3902 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.018
ω scans	θ_max = 25.3°, θ_min = 3.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −12→12
T_min = 0.968, T_max = 0.985	k = −10→12
8703 measured reflections	l = −13→14

Refinement top

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(F_o²) + (0.0397P)² + 0.3347P] where P = (F_o² + 2F_c²)/3
4526 reflections	(Δ/σ)_max < 0.001
365 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₃H₁₁NO₆	γ = 93.096 (3)°
M_r = 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)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	4526 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	3902 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.985	R_int = 0.018
8703 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
4526 reflections	Δρ_min = −0.24 e Å⁻³
365 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.968, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	8703, 4526, 3902
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

Alvim, J. Jr, Días, R. L. A., Castilhob, M. S., Olivab, G. & y Corréa, A. G. (2005). J. Braz. Chem. Soc. 16, 763–773. Google Scholar
Bigi, F., Carloni, S., Ferrari, L., Maggi, R., Mazzacani, A. & Sartori, G. (2001). Tetrahedron Lett. 42, 5203–5205. Web of Science CrossRef CAS Google Scholar
Cochard, F., Laronze, M., Sigaut, P., SAPI, J. & Laronze, J.-Y. (2004). Tetrahedron Lett. 45, 1703–1707. Web of Science CrossRef CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fillion, E. & Dumas, A.-M. (2008). J. Org. Chem. 73, 2920–2923. Web of Science CrossRef PubMed CAS Google Scholar
Fillion, E., Dumas, A. & Hogg, S. A. (2006). J. Org. Chem. 71, 9899–9902. Web of Science CSD CrossRef PubMed CAS Google Scholar
Mizukami, S., Kihara, N. & Endo, T. (1993). Tetrahedron Lett. 34, 7437–7440. CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Palasz, A., Jelska, K., Ozóg, M. & Serda, P. (2007). Monatsh. Chem. 138, 481–488. CAS Google Scholar
Scott, J. L. & Raston, C. L. (2000). Green Chem. 2, 245–247. Web of Science CrossRef CAS Google Scholar
Shaabani, A., Teimouri, M. B. & Bijanzadeh, H. R. (2004). Russ. J. Org. Chem. 40, 976–981. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X.-S., Zhang, M.-M., Jiang, H., Yaoa, C.-S. & Tua, S.-J. (2007). Tetrahedron, 63, 4439–4449. Web of Science CSD CrossRef CAS Google Scholar