3-Isobutyl 5-methyl 2,6-dimethyl-4-(2-nitro­phen­yl)pyridine-3,5-dicarboxyl­ate

Chen, H.; Luo, J.; Jing, L.-L.; Jiang, R.

doi:10.1107/S1600536809051988

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o86

doi:10.1107/S1600536809051988

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3-Isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate

Hui Chen,^a Jing Luo,^b Lin-Lin Jing ^a and Ru Jiang ^a ^*

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032, Xi-An, People's Republic of China, and ^bDepartment of Shannxi Institute for Food and Drug Control, Zhuque Road 431,710061 Xi-An, People's Republic of China
^*Correspondence e-mail: jiangru@fmmu.edu.cn

(Received 19 November 2009; accepted 3 December 2009; online 9 December 2009)

The title nitrophenyl pyridine compound, C₂₀H₂₂N₂O₆ was synthesized as a degradation product of the hypertension medication nisoldipine. The dihedral angle between the nitro-substituted phenyl ring and the pyridine ring is 75.5 (4)°. There are a number of C—H⋯O interactions between symmetry-related molecules>.

Related literature

For the preparation of the title compound see: Agbaba et al. (2004 ); Waldo & Correa (2001 ); Valentina et al. (2000 ). A derivative of the title compound, nisoldipine, has been evaluated as a calcium channel blocker with vasodilator properties, see: Ferrari et al. (2005 ); Marciniec et al. (2002 ); Kazda et al. (1980 ).

Experimental

Crystal data

C₂₀H₂₂N₂O₆
M_r = 386.40
Monoclinic, P 2₁ /c
a = 8.4222 (9) Å
b = 16.5850 (16) Å
c = 14.5011 (15) Å
β = 102.748 (2)°
V = 1975.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.989, T_max = 0.992
10199 measured reflections
3683 independent reflections
2718 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.154
S = 1.01
3683 reflections
259 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O4ⁱ	0.96	2.57	3.303 (3)	134
C13—H13B⋯O1ⁱⁱ	0.96	2.48	3.395 (3)	160
C14—H14B⋯O6ⁱⁱⁱ	0.96	2.52	3.221 (3)	130
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+2, -y, -z+2; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536809051988/pk2213sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051988/pk2213Isup2.hkl

checkCIF report

Comment top

Nisoldipine is a calcium channel blocker with vasodilator properties (Marciniec et al. 2002). It is used in several commercial preparations for treatment of hypertension (Kazda et al. 1980). It has been the subject of many analytical chemical investigations. Synthetic conditions result in side-reactions and formation of 1,4-dihydropyridines. This compound is a degradation product of nisoldipine.

The molecular structure is shown in Fig 1. The dihedral angle between the planes of phenyl and the pyridyl rings is 75.5 (4)°. There are a number of C—H···O interactions between symmetry-related molecules.

Related literature top

For the preparation of the title compound see: Agbaba et al. (2004); Waldo & Correa (2001); Valentina et al. (2000). A derivative of the title compound, nisoldipine, has been evaluated as a calcium channel blocker with vasodilator properties, see: Ferrari et al. (2005); Marciniec et al. (2002); Kazda et al. (1980).

Experimental top

A solution of nisoldipine (10 mmol) in 50 mL anhydrous ethanol was exposed to sunlight for 10 h at ambient temperature. 50 mL of water was added to the mixture and it was then filtered. The crude product was purified by flash chromatography (40/60 ethyl acetate/ether).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

3-Isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate top

Crystal data top

C₂₀H₂₂N₂O₆	F(000) = 816
M_r = 386.40	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3360 reflections
a = 8.4222 (9) Å	θ = 2.5–25.3°
b = 16.5850 (16) Å	µ = 0.10 mm⁻¹
c = 14.5011 (15) Å	T = 296 K
β = 102.748 (2)°	Block, colorless
V = 1975.6 (4) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3683 independent reflections
Radiation source: fine-focus sealed tube	2718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
T_min = 0.989, T_max = 0.992	k = −20→16
10199 measured reflections	l = −17→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.090P)² + 0.3869P] where P = (F_o² + 2F_c²)/3
3683 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O₆	V = 1975.6 (4) Å³
M_r = 386.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4222 (9) Å	µ = 0.10 mm⁻¹
b = 16.5850 (16) Å	T = 296 K
c = 14.5011 (15) Å	0.12 × 0.10 × 0.08 mm
β = 102.748 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3683 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2718 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.992	R_int = 0.020
10199 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	Δρ_max = 0.28 e Å⁻³
3683 reflections	Δρ_min = −0.21 e Å⁻³
259 parameters

Special details top

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.

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 > σ(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
C1	0.6743 (2)	0.17497 (11)	0.80315 (14)	0.0478 (5)
C2	0.5729 (3)	0.17694 (15)	0.71437 (18)	0.0685 (7)
H2	0.4764	0.1476	0.7020	0.082*
C3	0.6151 (4)	0.22258 (17)	0.64421 (17)	0.0765 (8)
H3	0.5462	0.2250	0.5846	0.092*
C4	0.7583 (3)	0.26433 (15)	0.66227 (16)	0.0700 (7)
H4	0.7877	0.2944	0.6145	0.084*
C5	0.8585 (3)	0.26212 (12)	0.75035 (15)	0.0546 (5)
H5	0.9559	0.2907	0.7614	0.066*
C6	0.8188 (2)	0.21826 (11)	0.82405 (13)	0.0412 (4)
C7	0.9348 (2)	0.22295 (10)	0.91819 (12)	0.0376 (4)
C8	1.0480 (2)	0.16259 (10)	0.95138 (13)	0.0403 (4)
C9	1.1657 (2)	0.17571 (11)	1.03476 (14)	0.0443 (5)
C10	1.0622 (2)	0.30249 (11)	1.05295 (14)	0.0457 (5)
C11	0.9444 (2)	0.29486 (10)	0.96861 (13)	0.0396 (4)
C12	1.0756 (3)	0.37681 (14)	1.11321 (18)	0.0692 (7)
H12A	1.1441	0.3659	1.1741	0.104*
H12B	0.9693	0.3923	1.1206	0.104*
H12C	1.1219	0.4198	1.0834	0.104*
C13	1.2955 (3)	0.11554 (13)	1.07470 (17)	0.0617 (6)
H13A	1.3734	0.1132	1.0354	0.093*
H13B	1.2471	0.0634	1.0768	0.093*
H13C	1.3492	0.1315	1.1375	0.093*
C14	1.1842 (3)	−0.01320 (15)	0.8348 (2)	0.0854 (9)
H14A	1.1540	−0.0537	0.8750	0.128*
H14B	1.2928	−0.0234	0.8272	0.128*
H14C	1.1102	−0.0147	0.7741	0.128*
C15	0.5685 (2)	0.41210 (14)	0.8841 (2)	0.0660 (6)
H15A	0.5611	0.4127	0.8164	0.079*
H15B	0.6066	0.4646	0.9092	0.079*
C16	0.4058 (3)	0.39528 (15)	0.90375 (19)	0.0657 (6)
H16	0.4179	0.3963	0.9725	0.079*
C17	0.2888 (3)	0.46254 (19)	0.8627 (2)	0.0936 (9)
H17A	0.3328	0.5134	0.8878	0.140*
H17B	0.1859	0.4537	0.8792	0.140*
H17C	0.2738	0.4630	0.7951	0.140*
C18	0.3416 (3)	0.31309 (17)	0.8696 (2)	0.0772 (7)
H18A	0.3292	0.3100	0.8023	0.116*
H18B	0.2380	0.3046	0.8853	0.116*
H18C	0.4167	0.2724	0.8994	0.116*
C19	1.0395 (2)	0.08501 (11)	0.89873 (15)	0.0471 (5)
C20	0.8372 (2)	0.36417 (11)	0.93117 (14)	0.0445 (4)
N1	0.62323 (19)	0.12682 (11)	0.87582 (15)	0.0588 (5)
N2	1.16919 (19)	0.24420 (10)	1.08444 (12)	0.0492 (4)
O1	0.9204 (2)	0.04564 (10)	0.87632 (16)	0.0907 (7)
O2	1.17751 (19)	0.06580 (9)	0.87727 (13)	0.0710 (5)
O3	0.68230 (15)	0.34992 (8)	0.92811 (11)	0.0558 (4)
O4	0.88648 (19)	0.42597 (9)	0.90518 (15)	0.0768 (5)
O5	0.6685 (2)	0.14682 (11)	0.95800 (12)	0.0725 (5)
O6	0.5362 (2)	0.06843 (12)	0.85059 (16)	0.0947 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0388 (10)	0.0479 (11)	0.0536 (11)	0.0019 (8)	0.0038 (8)	−0.0091 (9)
C2	0.0533 (13)	0.0721 (15)	0.0683 (16)	0.0055 (11)	−0.0123 (11)	−0.0226 (13)
C3	0.092 (2)	0.0798 (17)	0.0451 (13)	0.0281 (15)	−0.0131 (12)	−0.0107 (12)
C4	0.0932 (19)	0.0689 (15)	0.0452 (13)	0.0206 (14)	0.0095 (12)	0.0037 (11)
C5	0.0598 (13)	0.0534 (12)	0.0503 (12)	0.0046 (9)	0.0114 (10)	0.0032 (9)
C6	0.0401 (9)	0.0398 (9)	0.0419 (10)	0.0058 (7)	0.0055 (8)	−0.0032 (8)
C7	0.0324 (9)	0.0385 (9)	0.0416 (10)	−0.0045 (7)	0.0076 (7)	0.0009 (7)
C8	0.0373 (9)	0.0349 (9)	0.0481 (10)	−0.0035 (7)	0.0079 (8)	0.0025 (8)
C9	0.0385 (9)	0.0405 (10)	0.0516 (11)	−0.0036 (7)	0.0048 (8)	0.0042 (8)
C10	0.0406 (10)	0.0438 (10)	0.0505 (11)	−0.0046 (8)	0.0050 (8)	−0.0062 (9)
C11	0.0322 (9)	0.0383 (9)	0.0489 (10)	−0.0028 (7)	0.0100 (8)	−0.0006 (8)
C12	0.0661 (14)	0.0570 (14)	0.0759 (16)	−0.0003 (11)	−0.0032 (12)	−0.0225 (12)
C13	0.0572 (13)	0.0538 (13)	0.0644 (14)	0.0057 (10)	−0.0074 (10)	0.0045 (10)
C14	0.0797 (17)	0.0593 (15)	0.121 (2)	0.0004 (13)	0.0313 (16)	−0.0361 (15)
C15	0.0462 (12)	0.0578 (13)	0.0916 (17)	0.0121 (10)	0.0101 (11)	0.0198 (12)
C16	0.0487 (12)	0.0741 (15)	0.0734 (15)	0.0114 (11)	0.0116 (11)	0.0161 (12)
C17	0.0564 (15)	0.098 (2)	0.124 (3)	0.0277 (14)	0.0160 (15)	0.0310 (19)
C18	0.0513 (13)	0.0931 (19)	0.0862 (18)	−0.0068 (13)	0.0130 (12)	0.0095 (15)
C19	0.0409 (10)	0.0378 (10)	0.0592 (12)	−0.0002 (8)	0.0035 (9)	0.0003 (9)
C20	0.0402 (10)	0.0391 (10)	0.0533 (11)	−0.0018 (8)	0.0084 (8)	−0.0020 (8)
N1	0.0403 (9)	0.0596 (11)	0.0751 (13)	−0.0099 (8)	0.0099 (9)	−0.0080 (10)
N2	0.0433 (9)	0.0479 (9)	0.0512 (10)	−0.0021 (7)	−0.0010 (7)	−0.0025 (7)
O1	0.0535 (9)	0.0594 (10)	0.1577 (19)	−0.0133 (8)	0.0201 (11)	−0.0422 (11)
O2	0.0602 (9)	0.0568 (9)	0.1024 (13)	−0.0086 (7)	0.0317 (9)	−0.0292 (8)
O3	0.0370 (7)	0.0486 (8)	0.0804 (10)	0.0036 (6)	0.0101 (7)	0.0143 (7)
O4	0.0538 (9)	0.0472 (9)	0.1299 (16)	0.0000 (7)	0.0214 (9)	0.0233 (9)
O5	0.0717 (11)	0.0852 (12)	0.0627 (11)	−0.0205 (9)	0.0197 (8)	−0.0001 (9)
O6	0.0713 (11)	0.0836 (13)	0.1256 (17)	−0.0391 (10)	0.0141 (11)	−0.0118 (11)

Geometric parameters (Å, º) top

C1—C2	1.379 (3)	C13—H13B	0.9600
C1—C6	1.388 (3)	C13—H13C	0.9600
C1—N1	1.460 (3)	C14—O2	1.454 (3)
C2—C3	1.376 (4)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.365 (4)	C14—H14C	0.9600
C3—H3	0.9300	C15—O3	1.456 (2)
C4—C5	1.367 (3)	C15—C16	1.486 (3)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.393 (3)	C15—H15B	0.9700
C5—H5	0.9300	C16—C18	1.509 (4)
C6—C7	1.495 (2)	C16—C17	1.521 (3)
C7—C11	1.392 (2)	C16—H16	0.9800
C7—C8	1.393 (2)	C17—H17A	0.9600
C8—C9	1.401 (3)	C17—H17B	0.9600
C8—C19	1.490 (3)	C17—H17C	0.9600
C9—N2	1.342 (2)	C18—H18A	0.9600
C9—C13	1.499 (3)	C18—H18B	0.9600
C10—N2	1.332 (2)	C18—H18C	0.9600
C10—C11	1.400 (3)	C19—O1	1.181 (2)
C10—C12	1.501 (3)	C19—O2	1.307 (2)
C11—C20	1.488 (3)	C20—O4	1.197 (2)
C12—H12A	0.9600	C20—O3	1.317 (2)
C12—H12B	0.9600	N1—O6	1.221 (2)
C12—H12C	0.9600	N1—O5	1.214 (2)
C13—H13A	0.9600

C2—C1—C6	121.6 (2)	H13B—C13—H13C	109.5
C2—C1—N1	117.79 (19)	O2—C14—H14A	109.5
C6—C1—N1	120.59 (17)	O2—C14—H14B	109.5
C3—C2—C1	119.7 (2)	H14A—C14—H14B	109.5
C3—C2—H2	120.2	O2—C14—H14C	109.5
C1—C2—H2	120.2	H14A—C14—H14C	109.5
C4—C3—C2	119.9 (2)	H14B—C14—H14C	109.5
C4—C3—H3	120.0	O3—C15—C16	109.20 (18)
C2—C3—H3	120.0	O3—C15—H15A	109.8
C3—C4—C5	120.2 (2)	C16—C15—H15A	109.8
C3—C4—H4	119.9	O3—C15—H15B	109.8
C5—C4—H4	119.9	C16—C15—H15B	109.8
C4—C5—C6	121.8 (2)	H15A—C15—H15B	108.3
C4—C5—H5	119.1	C15—C16—C18	112.7 (2)
C6—C5—H5	119.1	C15—C16—C17	109.4 (2)
C1—C6—C5	116.75 (18)	C18—C16—C17	112.3 (2)
C1—C6—C7	126.24 (17)	C15—C16—H16	107.4
C5—C6—C7	117.00 (17)	C18—C16—H16	107.4
C11—C7—C8	118.55 (16)	C17—C16—H16	107.4
C11—C7—C6	118.36 (15)	C16—C17—H17A	109.5
C8—C7—C6	122.52 (15)	C16—C17—H17B	109.5
C7—C8—C9	119.11 (16)	H17A—C17—H17B	109.5
C7—C8—C19	119.47 (16)	C16—C17—H17C	109.5
C9—C8—C19	121.41 (16)	H17A—C17—H17C	109.5
N2—C9—C8	121.50 (16)	H17B—C17—H17C	109.5
N2—C9—C13	115.35 (17)	C16—C18—H18A	109.5
C8—C9—C13	123.15 (17)	C16—C18—H18B	109.5
N2—C10—C11	121.95 (17)	H18A—C18—H18B	109.5
N2—C10—C12	116.00 (17)	C16—C18—H18C	109.5
C11—C10—C12	122.05 (17)	H18A—C18—H18C	109.5
C7—C11—C10	118.98 (16)	H18B—C18—H18C	109.5
C7—C11—C20	120.65 (16)	O1—C19—O2	123.08 (19)
C10—C11—C20	120.30 (16)	O1—C19—C8	124.05 (19)
C10—C12—H12A	109.5	O2—C19—C8	112.84 (16)
C10—C12—H12B	109.5	O4—C20—O3	123.53 (18)
H12A—C12—H12B	109.5	O4—C20—C11	123.49 (17)
C10—C12—H12C	109.5	O3—C20—C11	112.97 (15)
H12A—C12—H12C	109.5	O6—N1—O5	123.3 (2)
H12B—C12—H12C	109.5	O6—N1—C1	118.1 (2)
C9—C13—H13A	109.5	O5—N1—C1	118.68 (17)
C9—C13—H13B	109.5	C10—N2—C9	119.82 (16)
H13A—C13—H13B	109.5	C19—O2—C14	116.10 (18)
C9—C13—H13C	109.5	C20—O3—C15	116.05 (15)
H13A—C13—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O4ⁱ	0.96	2.57	3.303 (3)	134
C13—H13B···O1ⁱⁱ	0.96	2.48	3.395 (3)	160
C14—H14B···O6ⁱⁱⁱ	0.96	2.52	3.221 (3)	130

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₂O₆
M_r	386.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.4222 (9), 16.5850 (16), 14.5011 (15)
β (°)	102.748 (2)
V (Å³)	1975.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.989, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	10199, 3683, 2718
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.154, 1.01
No. of reflections	3683
No. of parameters	259
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O4ⁱ	0.96	2.57	3.303 (3)	134
C13—H13B···O1ⁱⁱ	0.96	2.48	3.395 (3)	160
C14—H14B···O6ⁱⁱⁱ	0.96	2.52	3.221 (3)	130

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

Acknowledgements

We thank the Natural Science Foundation of China (Nos. 30901883, 20972189) for financial support.

References

Agbaba, D., Vucicevic, K. & Marinkovic, V. (2004). Chromatographia, 60, 223–227. Web of Science CrossRef CAS Google Scholar
Bruker (2001). SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ferrari, M., Ghezzi, M., Alberelli, C. & &Ambrosini, L. (2005). US Patent 2005/0240022 A1. Google Scholar
Kazda, S., Garhoff, B., Meyer, H., Schlossmann, K., Stoepel, K., Towart, R., Vater, W. & Wehinger, E. (1980). Arzneim. Forsch. Drug Res. 30, 2144–2162. CAS Google Scholar
Marciniec, B., Jaroszkiewicz, E. & Ogrodowczyk, M. (2002). Int. J. Pharm. 233, 207–215. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Valentina, M., Danica, A., Katarina, K. R., Jozef, C. & &Dobrila, Z. S. (2000). Farmaco, 55, 128–133. Web of Science PubMed Google Scholar
Waldo, H. & Correa, J. L. S. (2001). Green Chem. 3, 296–301. Google Scholar

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Volume 66| Part 1| January 2010| Page o86

doi:10.1107/S1600536809051988

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Iso­butyl 5-methyl 2,6-di­methyl-4-(2-nitro­phen­yl)pyridine-3,5-di­carboxyl­ate

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Experimental

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Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate