2,2-Dimethyl-5-[(2-nitro­anilino)methyl­idene]-1,3-dioxane-4,6-dione

He, Y.; Wu, J.; Tong, R.; Shi, J.

doi:10.1107/S1600536811014358

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1216

doi:10.1107/S1600536811014358

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2,2-Dimethyl-5-[(2-nitroanilino)methylidene]-1,3-dioxane-4,6-dione

Yu-xin He,^a Jin-wei Wu,^a Rong-sheng Tong ^b and Jian-you Shi ^b ^*

^aBioengineering College, Xihua University, Chengdu, Sichuan 610039, People's Republic of China, and ^bSichuan Academy of Medical Sciences and Sichuan Provincial People's Hospital, Chengdu, Sichuan 610072, People's Republic of China
^*Correspondence e-mail: shijianyoude@126.com

(Received 9 April 2011; accepted 16 April 2011; online 29 April 2011)

The crystal of the title compound, C₁₃H₁₂N₂O₆, contains a bifurcated intramolecular hydrogen bond between the N—H group and one of the O atoms from both the nitro group and the dioxane-4,6-dione moiety. In addition, molecules are linked by a series of intermolecular C—H⋯O secondary interactions. The dihedral angles between the benzene ring and the nitro group and the conjugated part of the dioxane-4,6-dione moiety are 19.1 (2) and 17.89 (7)°, respectively.

Related literature

The title compound is an important intermediate drug discovery. For the synthesis and structures of related antitumor precursors, see: Cassis et al. (1985 ). For related literature, see Dolomanov et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₆
M_r = 292.25
Monoclinic, P 2₁ /c
a = 6.3860 (2) Å
b = 17.3800 (5) Å
c = 11.9338 (3) Å
β = 90.622 (3)°
V = 1324.44 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 150 K
0.42 × 0.35 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.993, T_max = 1.0
9157 measured reflections
2693 independent reflections
2212 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.097
S = 1.03
2693 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5	0.88	1.97	2.6403 (16)	132
N1—H1⋯O3	0.88	2.10	2.7439 (16)	130
C7—H7⋯O4ⁱ	0.95	2.40	3.0852 (18)	129
C10—H10⋯O6ⁱⁱ	0.95	2.48	3.4219 (19)	170
C11—H11⋯O1ⁱⁱⁱ	0.95	2.53	3.4508 (18)	162
C13—H13⋯O4ⁱ	0.95	2.53	3.4445 (18)	161
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y+1, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014358/bv2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014358/bv2184Isup2.hkl

checkCIF report

Comment top

2,2-Dimethyl-5-[(2-nitrophenylamino)-methylene]-[1,3]dioxane-4,6-dione, C₁₃H₁₂N₂O₆, is a key intermediate which can be used to synthesize the 4(1H)quinolone derivatives by thermolysis, which can then be used as precursors for anti-malarial agents or anti-cancer agents. The structure contains an bifurcated intramolecular hydrogen bond between the N-H and one of the O's from both the nitro group and the dioxane-4,6-dione moiety. In addition the molecules are linked by a series of intermolecular C-H···O secondary interactions. The dihedral angles between the phenyl group and both the nitro and conjugated part of the dioxane-4,6-dione moiety are 19.1 (2)° and 17.89 (7)°, respectively.

Related literature top

Please supply related literature section.

Experimental top

A mixture of 2,2-dimethyl-1,3-dioxane-4,6-dione(1.44 g, 0.01 mol) and methylorthoformate (1.27 g, 0.012 mol) was heated to reflux for 0.5 h, then 2-nitroaniline(1.38 g, 0.01 mol) in ethanol (20 mL) was added into the above solution. The mixture was heated under reflux for another 2 h and poured into cold water then filtered to obtain a powder. Single crystals were obtained from the powder in CH₂Cl₂ and methanol after 3 days.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing the bifurcated intramolecular hydrogen bond.
	Fig. 2. Fi. 2. The packing diagram for the title compound viewed down the a axis, showing the intermolecular C—H···O interactions.

2,2-Dimethyl-5-[(2-nitroanilino)methylidene]-1,3-dioxane-4,6-dione top

Crystal data top

C₁₃H₁₂N₂O₆	F(000) = 608
M_r = 292.25	D_x = 1.466 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3956 reflections
a = 6.3860 (2) Å	θ = 2.9–29.1°
b = 17.3800 (5) Å	µ = 0.12 mm⁻¹
c = 11.9338 (3) Å	T = 150 K
β = 90.622 (3)°	Block, colourless
V = 1324.44 (7) Å³	0.42 × 0.35 × 0.25 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2693 independent reflections
Radiation source: fine-focus sealed tube	2212 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = 0→21
T_min = 0.993, T_max = 1.0	l = 0→14
9157 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0439P)² + 0.3082P] where P = (F_o² + 2F_c²)/3
2693 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₃H₁₂N₂O₆	V = 1324.44 (7) Å³
M_r = 292.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.3860 (2) Å	µ = 0.12 mm⁻¹
b = 17.3800 (5) Å	T = 150 K
c = 11.9338 (3) Å	0.42 × 0.35 × 0.25 mm
β = 90.622 (3)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2693 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2212 reflections with I > 2σ(I)
T_min = 0.993, T_max = 1.0	R_int = 0.027
9157 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
2693 reflections	Δρ_min = −0.22 e Å⁻³
192 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.38713 (16)	0.72407 (6)	0.58099 (8)	0.0262 (3)
O2	0.14846 (17)	0.64025 (6)	0.66934 (8)	0.0260 (3)
O3	0.57240 (17)	0.68777 (6)	0.43461 (9)	0.0287 (3)
O4	0.10877 (16)	0.51978 (6)	0.61477 (8)	0.0255 (3)
O5	0.7590 (2)	0.62314 (7)	0.21713 (11)	0.0434 (3)
O6	0.9663 (2)	0.55108 (8)	0.12201 (10)	0.0452 (3)
N1	0.45628 (19)	0.55433 (7)	0.32793 (9)	0.0215 (3)
H1	0.5390	0.5948	0.3241	0.026*
N2	0.7992 (2)	0.56246 (8)	0.16919 (10)	0.0302 (3)
C1	0.1846 (2)	0.71834 (8)	0.63308 (12)	0.0254 (3)
C2	0.4337 (2)	0.67221 (8)	0.49964 (11)	0.0218 (3)
C3	0.3173 (2)	0.60086 (8)	0.50100 (11)	0.0204 (3)
C4	0.1833 (2)	0.58240 (8)	0.59513 (11)	0.0211 (3)
C5	0.1985 (3)	0.76619 (10)	0.73797 (13)	0.0358 (4)
H5A	0.3132	0.7472	0.7856	0.054*
H5B	0.0664	0.7626	0.7787	0.054*
H5C	0.2249	0.8200	0.7180	0.054*
C6	0.0136 (3)	0.74320 (10)	0.55292 (13)	0.0329 (4)
H6A	0.0098	0.7084	0.4884	0.049*
H6B	0.0413	0.7958	0.5273	0.049*
H6C	−0.1215	0.7417	0.5910	0.049*
C7	0.3356 (2)	0.54685 (8)	0.41734 (12)	0.0204 (3)
H7	0.2563	0.5009	0.4240	0.025*
C8	0.4737 (2)	0.50006 (8)	0.24088 (12)	0.0216 (3)
C9	0.6411 (2)	0.50180 (8)	0.16525 (12)	0.0238 (3)
C10	0.6632 (3)	0.44616 (9)	0.08294 (12)	0.0295 (4)
H10	0.7784	0.4482	0.0333	0.035*
C11	0.5182 (3)	0.38812 (9)	0.07327 (13)	0.0323 (4)
H11	0.5328	0.3498	0.0171	0.039*
C12	0.3506 (3)	0.38574 (9)	0.14598 (14)	0.0334 (4)
H12	0.2503	0.3456	0.1394	0.040*
C13	0.3277 (2)	0.44111 (9)	0.22799 (13)	0.0283 (4)
H13	0.2105	0.4390	0.2763	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0282 (6)	0.0224 (5)	0.0279 (6)	−0.0010 (4)	−0.0001 (5)	−0.0038 (4)
O2	0.0299 (6)	0.0280 (6)	0.0201 (5)	0.0010 (5)	0.0039 (4)	−0.0033 (4)
O3	0.0266 (6)	0.0276 (6)	0.0322 (6)	−0.0059 (5)	0.0055 (5)	0.0002 (5)
O4	0.0235 (6)	0.0290 (6)	0.0239 (5)	−0.0056 (4)	0.0029 (4)	0.0009 (4)
O5	0.0497 (8)	0.0287 (6)	0.0524 (8)	−0.0103 (6)	0.0263 (6)	−0.0056 (6)
O6	0.0343 (7)	0.0534 (8)	0.0484 (8)	−0.0045 (6)	0.0235 (6)	−0.0030 (6)
N1	0.0198 (7)	0.0203 (6)	0.0245 (6)	−0.0010 (5)	0.0048 (5)	−0.0014 (5)
N2	0.0316 (8)	0.0324 (7)	0.0269 (7)	−0.0017 (6)	0.0115 (6)	0.0042 (6)
C1	0.0283 (8)	0.0248 (8)	0.0230 (7)	0.0031 (7)	0.0007 (6)	−0.0027 (6)
C2	0.0213 (8)	0.0227 (7)	0.0213 (7)	0.0017 (6)	−0.0027 (6)	0.0006 (6)
C3	0.0178 (7)	0.0214 (7)	0.0219 (7)	0.0012 (6)	0.0014 (6)	0.0000 (6)
C4	0.0172 (7)	0.0268 (8)	0.0193 (7)	0.0002 (6)	−0.0024 (6)	−0.0004 (6)
C5	0.0463 (11)	0.0336 (9)	0.0275 (8)	0.0052 (8)	−0.0038 (8)	−0.0085 (7)
C6	0.0332 (10)	0.0365 (9)	0.0289 (8)	0.0100 (7)	−0.0046 (7)	−0.0062 (7)
C7	0.0159 (7)	0.0209 (7)	0.0245 (7)	0.0001 (6)	0.0000 (6)	0.0024 (6)
C8	0.0226 (8)	0.0208 (7)	0.0214 (7)	0.0045 (6)	0.0015 (6)	0.0007 (6)
C9	0.0250 (8)	0.0245 (7)	0.0219 (7)	0.0029 (6)	0.0044 (6)	0.0039 (6)
C10	0.0344 (9)	0.0317 (9)	0.0227 (8)	0.0095 (7)	0.0068 (7)	0.0028 (6)
C11	0.0435 (10)	0.0284 (8)	0.0251 (8)	0.0078 (7)	0.0017 (7)	−0.0064 (6)
C12	0.0368 (10)	0.0286 (8)	0.0347 (9)	−0.0043 (7)	0.0009 (7)	−0.0065 (7)
C13	0.0247 (9)	0.0310 (8)	0.0294 (8)	−0.0021 (7)	0.0055 (7)	−0.0044 (6)

Geometric parameters (Å, º) top

O1—C2	1.3600 (17)	C5—H5A	0.9800
O1—C1	1.4446 (17)	C5—H5B	0.9800
O2—C4	1.3598 (17)	C5—H5C	0.9800
O2—C1	1.4438 (17)	C6—H6A	0.9800
O3—C2	1.2144 (17)	C6—H6B	0.9800
O4—C4	1.2118 (17)	C6—H6C	0.9800
O5—N2	1.2283 (17)	C7—H7	0.9500
O6—N2	1.2276 (17)	C8—C13	1.393 (2)
N1—C7	1.3292 (18)	C8—C9	1.4066 (19)
N1—C8	1.4084 (18)	C9—C10	1.387 (2)
N1—H1	0.8808	C10—C11	1.373 (2)
N2—C9	1.460 (2)	C10—H10	0.9500
C1—C5	1.505 (2)	C11—C12	1.386 (2)
C1—C6	1.507 (2)	C11—H11	0.9500
C2—C3	1.446 (2)	C12—C13	1.382 (2)
C3—C7	1.376 (2)	C12—H12	0.9500
C3—C4	1.4551 (19)	C13—H13	0.9500

C2—O1—C1	117.73 (11)	H5B—C5—H5C	109.5
C4—O2—C1	118.16 (10)	C1—C6—H6A	109.5
C7—N1—C8	125.29 (12)	C1—C6—H6B	109.5
C7—N1—H1	118.2	H6A—C6—H6B	109.5
C8—N1—H1	116.4	C1—C6—H6C	109.5
O6—N2—O5	122.62 (14)	H6A—C6—H6C	109.5
O6—N2—C9	118.24 (13)	H6B—C6—H6C	109.5
O5—N2—C9	119.12 (12)	N1—C7—C3	124.77 (14)
O2—C1—O1	109.90 (11)	N1—C7—H7	117.6
O2—C1—C5	106.16 (12)	C3—C7—H7	117.6
O1—C1—C5	105.96 (13)	C13—C8—C9	117.22 (13)
O2—C1—C6	110.05 (13)	C13—C8—N1	121.06 (13)
O1—C1—C6	110.67 (12)	C9—C8—N1	121.70 (13)
C5—C1—C6	113.91 (13)	C10—C9—C8	121.56 (14)
O3—C2—O1	118.37 (13)	C10—C9—N2	116.77 (13)
O3—C2—C3	125.22 (13)	C8—C9—N2	121.67 (13)
O1—C2—C3	116.35 (12)	C11—C10—C9	119.87 (15)
C7—C3—C2	121.94 (13)	C11—C10—H10	120.1
C7—C3—C4	117.71 (13)	C9—C10—H10	120.1
C2—C3—C4	120.28 (12)	C10—C11—C12	119.61 (14)
O4—C4—O2	118.07 (12)	C10—C11—H11	120.2
O4—C4—C3	125.65 (13)	C12—C11—H11	120.2
O2—C4—C3	116.21 (12)	C13—C12—C11	120.75 (15)
C1—C5—H5A	109.5	C13—C12—H12	119.6
C1—C5—H5B	109.5	C11—C12—H12	119.6
H5A—C5—H5B	109.5	C12—C13—C8	120.97 (14)
C1—C5—H5C	109.5	C12—C13—H13	119.5
H5A—C5—H5C	109.5	C8—C13—H13	119.5

C4—O2—C1—O1	−49.01 (16)	C2—C3—C7—N1	−0.9 (2)
C4—O2—C1—C5	−163.17 (13)	C4—C3—C7—N1	−177.98 (13)
C4—O2—C1—C6	73.12 (16)	C7—N1—C8—C13	15.3 (2)
C2—O1—C1—O2	50.40 (15)	C7—N1—C8—C9	−163.14 (14)
C2—O1—C1—C5	164.70 (12)	C13—C8—C9—C10	−1.6 (2)
C2—O1—C1—C6	−71.36 (15)	N1—C8—C9—C10	176.90 (14)
C1—O1—C2—O3	160.00 (13)	C13—C8—C9—N2	178.09 (14)
C1—O1—C2—C3	−22.41 (18)	N1—C8—C9—N2	−3.4 (2)
O3—C2—C3—C7	−8.8 (2)	O6—N2—C9—C10	−18.5 (2)
O1—C2—C3—C7	173.82 (13)	O5—N2—C9—C10	159.99 (15)
O3—C2—C3—C4	168.19 (14)	O6—N2—C9—C8	161.84 (14)
O1—C2—C3—C4	−9.2 (2)	O5—N2—C9—C8	−19.7 (2)
C1—O2—C4—O4	−163.13 (13)	C8—C9—C10—C11	0.7 (2)
C1—O2—C4—C3	19.81 (18)	N2—C9—C10—C11	−178.97 (14)
C7—C3—C4—O4	10.9 (2)	C9—C10—C11—C12	0.1 (2)
C2—C3—C4—O4	−166.25 (14)	C10—C11—C12—C13	0.0 (2)
C7—C3—C4—O2	−172.34 (13)	C11—C12—C13—C8	−1.0 (3)
C2—C3—C4—O2	10.6 (2)	C9—C8—C13—C12	1.7 (2)
C8—N1—C7—C3	−178.89 (14)	N1—C8—C13—C12	−176.80 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.88	1.97	2.6403 (16)	132
N1—H1···O3	0.88	2.10	2.7439 (16)	130
C7—H7···O4ⁱ	0.95	2.40	3.0852 (18)	129
C10—H10···O6ⁱⁱ	0.95	2.48	3.4219 (19)	170
C11—H11···O1ⁱⁱⁱ	0.95	2.53	3.4508 (18)	162
C13—H13···O4ⁱ	0.95	2.53	3.4445 (18)	161

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₆
M_r	292.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	6.3860 (2), 17.3800 (5), 11.9338 (3)
β (°)	90.622 (3)
V (Å³)	1324.44 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.42 × 0.35 × 0.25

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.993, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	9157, 2693, 2212
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.097, 1.03
No. of reflections	2693
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.88	1.97	2.6403 (16)	131.7
N1—H1···O3	0.88	2.10	2.7439 (16)	129.8
C7—H7···O4ⁱ	0.95	2.40	3.0852 (18)	128.9
C10—H10···O6ⁱⁱ	0.95	2.48	3.4219 (19)	170.1
C11—H11···O1ⁱⁱⁱ	0.95	2.53	3.4508 (18)	162.2
C13—H13···O4ⁱ	0.95	2.53	3.4445 (18)	160.6

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) −x+1, y−1/2, −z+1/2.

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection. This work was supported by the Research Fund of the Key Laboratory of TCM Biotechnology (Xihua University).

References

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