5-Methyl 3-(2-methyl­prop-3-yl) 2,6-di­methyl-4-(2-nitro­sophen­yl)pyridine-3,5-dicarboxyl­ate

Chen, H.; Qu, D.; Wang, Q.-F.; Jiang, R.

doi:10.1107/S1600536810005088

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o619

doi:10.1107/S1600536810005088

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5-Methyl 3-(2-methylprop-3-yl) 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate

Hui Chen,^a Ding Qu,^a Qiao-Feng Wang ^a and Ru Jiang ^a ^*

^aSchool of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
^*Correspondence e-mail: jiangru@fmmu.edu.cn

(Received 26 January 2010; accepted 8 February 2010; online 13 February 2010)

In the title compound, C₂₀H₂₂N₂O₅, a photo-degradation product of the hypertension drug nisoldipine, the dihedral angle between the nitrosophenyl ring and the pyridine ring is 75.7 (3)°. In the crystal structure, weak C—H⋯O hydrogen bonds help to establish the packing.

Related literature

For general background to nisoldipine derivatives, see: Marciniec et al. (2002 ).

Experimental

Crystal data

C₂₀H₂₂N₂O₅
M_r = 370.40
Triclinic, $[P \overline 1]$
a = 7.1831 (4) Å
b = 9.7819 (6) Å
c = 15.0245 (9) Å
α = 89.488 (3)°
β = 81.201 (3)°
γ = 70.625 (3)°
V = 983.19 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.42 × 0.28 × 0.22 mm

Data collection

Bruker APEX II CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.963, T_max = 0.980
5353 measured reflections
3623 independent reflections
2500 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.311
S = 1.01
3623 reflections
250 parameters
H-atom parameters not refined
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O1ⁱ	0.96	2.39	3.344 (5)	172
C14—H14B⋯O4ⁱⁱ	0.96	2.52	3.472 (5)	174
Symmetry codes: (i) x+1, y-1, z; (ii) -x+1, -y, -z+1.

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 datablocks global, I. DOI: 10.1107/S1600536810005088/hb5320sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005088/hb5320Isup2.hkl

checkCIF report

Comment top

Nisoldipine has been the subject of many analytical chemical investigations due to the commercial preparations for treatment of hypertension (Marciniec et al., 2002). Here, we describe the synthesis and structural characterization of the title compound.

The molecular structure of the title compound is shown in Fig. 1. In this structure, the dihedral angle between the nitrosophenyl ring and the pyridine ring is 75.7 (3)°. Weak C—H···O hydrogen bonding between the cations and anions leads to a consolidation of the structure.

Related literature top

For general background to nisoldipine derivatives, see: Marciniec et al. (2002).

Experimental top

A solution of nisoldipine (10 mmol) in 50 ml acetone was exposed to sunlight for 5 h at ambient temperature. To the mixture was added 50 ml water, followed by filtration. The crude product was purified by flash chromatography on silica gel (1:1 ethyl acetate/hexane). Anal. C₂₀H₂₂N₂O₅: C, 64.79; H, 5.94; N, 7.56. Found: C, 64.65; H, 5.82; N, 7.50 %. Colourless blocks of (I) were recrystallised from ethanol.

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. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level; H atoms are given as spheres of arbitrary radius.

5-Methyl 3-(2-methylprop-3-yl) 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate top

Crystal data top

C₂₀H₂₂N₂O₅	Z = 2
M_r = 370.40	F(000) = 392
Triclinic, P1	D_x = 1.251 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1831 (4) Å	Cell parameters from 1617 reflections
b = 9.7819 (6) Å	θ = 2.2–24.3°
c = 15.0245 (9) Å	µ = 0.09 mm⁻¹
α = 89.488 (3)°	T = 296 K
β = 81.201 (3)°	Block, colourless
γ = 70.625 (3)°	0.42 × 0.28 × 0.22 mm
V = 983.19 (10) Å³

Data collection top

Bruker APEX II CCD diffractometer	3623 independent reflections
Radiation source: fine-focus sealed tube	2500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.963, T_max = 0.980	k = −11→11
5353 measured reflections	l = −15→18

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.311	H-atom parameters not refined
S = 1.01	w = 1/[σ²(F_o²) + (0.240P)²] where P = (F_o² + 2F_c²)/3
3623 reflections	(Δ/σ)_max < 0.001
250 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O₅	γ = 70.625 (3)°
M_r = 370.40	V = 983.19 (10) Å³
Triclinic, P1	Z = 2
a = 7.1831 (4) Å	Mo Kα radiation
b = 9.7819 (6) Å	µ = 0.09 mm⁻¹
c = 15.0245 (9) Å	T = 296 K
α = 89.488 (3)°	0.42 × 0.28 × 0.22 mm
β = 81.201 (3)°

Data collection top

Bruker APEX II CCD diffractometer	3623 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2500 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.980	R_int = 0.015
5353 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.311	H-atom parameters not refined
S = 1.01	Δρ_max = 0.81 e Å⁻³
3623 reflections	Δρ_min = −0.29 e Å⁻³
250 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 > 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	0.6145 (4)	0.4193 (3)	0.3529 (2)	0.0509 (7)
C2	0.7137 (5)	0.5026 (4)	0.3888 (2)	0.0619 (8)
H2	0.6424	0.5893	0.4215	0.074*
C3	0.9183 (5)	0.4525 (4)	0.3742 (2)	0.0686 (10)
H3	0.9872	0.5068	0.3963	0.082*
C4	1.0230 (5)	0.3236 (4)	0.3276 (2)	0.0655 (9)
H4	1.1620	0.2908	0.3190	0.079*
C5	0.9240 (4)	0.2413 (4)	0.2931 (2)	0.0597 (8)
H5	0.9969	0.1538	0.2615	0.072*
C6	0.7173 (4)	0.2887 (3)	0.30541 (18)	0.0471 (7)
C7	0.6111 (4)	0.2014 (3)	0.26614 (18)	0.0486 (7)
C8	0.5973 (4)	0.0750 (3)	0.30544 (19)	0.0493 (7)
C9	0.5000 (5)	−0.0045 (3)	0.2660 (2)	0.0573 (8)
C10	0.4346 (5)	0.1561 (4)	0.1519 (2)	0.0624 (8)
C11	0.5245 (5)	0.2442 (3)	0.1897 (2)	0.0589 (8)
C12	0.6737 (4)	0.0337 (3)	0.3918 (2)	0.0527 (7)
C13	0.8802 (7)	−0.1539 (4)	0.4692 (3)	0.0913 (13)
H13A	0.8912	−0.0762	0.5043	0.137*
H13B	1.0089	−0.2278	0.4550	0.137*
H13C	0.7878	−0.1942	0.5030	0.137*
C14	0.4632 (7)	−0.1378 (4)	0.3078 (3)	0.0812 (11)
H14A	0.3521	−0.1524	0.2859	0.122*
H14B	0.4338	−0.1233	0.3722	0.122*
H14C	0.5803	−0.2214	0.2915	0.122*
C15	0.3426 (7)	0.1944 (5)	0.0689 (3)	0.0908 (13)
H15A	0.3202	0.1112	0.0453	0.136*
H15B	0.4307	0.2246	0.0246	0.136*
H15C	0.2174	0.2720	0.0831	0.136*
C16	0.5224 (5)	0.3875 (4)	0.1491 (2)	0.0652 (9)
C17	0.3105 (6)	0.6240 (4)	0.1237 (3)	0.0798 (11)
H17A	0.3503	0.6115	0.0589	0.096*
H17B	0.3922	0.6714	0.1479	0.096*
C18	0.0950 (7)	0.7135 (4)	0.1464 (3)	0.0862 (12)
H18	0.0635	0.7300	0.2120	0.103*
C19	−0.0422 (8)	0.6433 (6)	0.1188 (4)	0.1166 (18)
H19A	−0.0070	0.6179	0.0554	0.175*
H19B	−0.1771	0.7092	0.1313	0.175*
H19C	−0.0314	0.5573	0.1519	0.175*
C20	0.0630 (9)	0.8621 (5)	0.1047 (4)	0.1198 (18)
H20A	0.1012	0.8489	0.0404	0.180*
H20B	0.1431	0.9096	0.1287	0.180*
H20C	−0.0755	0.9207	0.1188	0.180*
N1	0.4005 (4)	0.4598 (3)	0.36627 (18)	0.0646 (8)
N2	0.4221 (4)	0.0355 (3)	0.19043 (18)	0.0635 (7)
O1	0.3121 (4)	0.5800 (3)	0.4003 (2)	0.0954 (10)
O2	0.3373 (4)	0.4833 (3)	0.16329 (17)	0.0769 (8)
O3	0.6613 (4)	0.4107 (3)	0.1127 (2)	0.0913 (9)
O4	0.6244 (4)	0.1108 (2)	0.45823 (15)	0.0714 (7)
O5	0.8089 (4)	−0.0987 (2)	0.38649 (16)	0.0771 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0461 (15)	0.0539 (16)	0.0569 (16)	−0.0199 (13)	−0.0133 (12)	0.0081 (13)
C2	0.069 (2)	0.0572 (18)	0.0674 (19)	−0.0264 (15)	−0.0207 (16)	0.0038 (14)
C3	0.067 (2)	0.082 (2)	0.076 (2)	−0.0430 (18)	−0.0258 (17)	0.0156 (18)
C4	0.0428 (16)	0.083 (2)	0.078 (2)	−0.0264 (16)	−0.0173 (15)	0.0088 (18)
C5	0.0468 (16)	0.0646 (19)	0.0653 (18)	−0.0144 (14)	−0.0108 (14)	0.0018 (14)
C6	0.0467 (15)	0.0532 (16)	0.0468 (14)	−0.0213 (12)	−0.0142 (12)	0.0114 (12)
C7	0.0434 (14)	0.0519 (16)	0.0500 (15)	−0.0143 (12)	−0.0095 (12)	0.0033 (12)
C8	0.0463 (15)	0.0454 (15)	0.0526 (15)	−0.0094 (12)	−0.0104 (12)	0.0016 (12)
C9	0.0680 (19)	0.0475 (16)	0.0566 (17)	−0.0188 (14)	−0.0123 (14)	0.0018 (13)
C10	0.069 (2)	0.067 (2)	0.0594 (18)	−0.0290 (16)	−0.0223 (15)	0.0063 (15)
C11	0.0603 (18)	0.0646 (19)	0.0587 (17)	−0.0262 (15)	−0.0180 (14)	0.0102 (14)
C12	0.0525 (16)	0.0487 (16)	0.0580 (17)	−0.0183 (13)	−0.0093 (13)	0.0062 (13)
C13	0.102 (3)	0.075 (2)	0.086 (3)	−0.001 (2)	−0.046 (2)	0.018 (2)
C14	0.118 (3)	0.066 (2)	0.078 (2)	−0.048 (2)	−0.032 (2)	0.0136 (17)
C15	0.135 (4)	0.091 (3)	0.074 (2)	−0.057 (3)	−0.056 (2)	0.020 (2)
C16	0.069 (2)	0.084 (2)	0.0529 (17)	−0.0330 (19)	−0.0217 (16)	0.0143 (16)
C17	0.096 (3)	0.069 (2)	0.081 (2)	−0.030 (2)	−0.027 (2)	0.0173 (18)
C18	0.094 (3)	0.067 (2)	0.093 (3)	−0.015 (2)	−0.030 (2)	0.0032 (19)
C19	0.104 (4)	0.104 (4)	0.146 (5)	−0.031 (3)	−0.043 (3)	0.018 (3)
C20	0.139 (5)	0.073 (3)	0.144 (5)	−0.022 (3)	−0.041 (4)	0.015 (3)
N1	0.0495 (15)	0.0658 (17)	0.0748 (17)	−0.0131 (12)	−0.0125 (13)	−0.0023 (14)
N2	0.0762 (18)	0.0596 (16)	0.0632 (16)	−0.0274 (13)	−0.0253 (13)	0.0026 (12)
O1	0.0593 (15)	0.0809 (18)	0.132 (2)	−0.0068 (13)	−0.0088 (16)	−0.0327 (17)
O2	0.0765 (17)	0.0701 (15)	0.0836 (17)	−0.0239 (13)	−0.0133 (13)	0.0226 (12)
O3	0.0819 (18)	0.114 (2)	0.0919 (19)	−0.0493 (16)	−0.0209 (15)	0.0420 (17)
O4	0.0996 (19)	0.0565 (14)	0.0532 (13)	−0.0172 (12)	−0.0177 (12)	0.0036 (10)
O5	0.0776 (16)	0.0629 (14)	0.0695 (14)	0.0105 (12)	−0.0246 (12)	0.0006 (11)

Geometric parameters (Å, º) top

C1—C2	1.405 (4)	C13—H13A	0.9600
C1—N1	1.436 (4)	C13—H13B	0.9600
C1—C6	1.384 (4)	C13—H13C	0.9600
C2—C3	1.369 (5)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.368 (5)	C14—H14C	0.9600
C3—H3	0.9300	C15—H15A	0.9601
C4—C5	1.387 (5)	C15—H15B	0.9601
C4—H4	0.9300	C15—H15C	0.9601
C5—C6	1.383 (4)	C16—O3	1.152 (4)
C5—H5	0.9300	C16—O2	1.335 (4)
C6—C7	1.496 (4)	C17—O2	1.458 (4)
C7—C11	1.386 (4)	C17—C18	1.491 (6)
C7—C8	1.392 (4)	C17—H17A	0.9700
C8—C9	1.393 (4)	C17—H17B	0.9700
C8—C12	1.487 (4)	C18—C19	1.481 (7)
C9—N2	1.340 (4)	C18—C20	1.538 (6)
C9—C14	1.525 (4)	C18—H18	0.9800
C10—N2	1.333 (4)	C19—H19A	0.9600
C10—C11	1.404 (4)	C19—H19B	0.9600
C10—C15	1.487 (4)	C19—H19C	0.9600
C11—C16	1.520 (4)	C20—H20A	0.9600
C12—O4	1.191 (4)	C20—H20B	0.9600
C12—O5	1.331 (4)	C20—H20C	0.9600
C13—O5	1.448 (4)	N1—O1	1.210 (4)

C2—C1—N1	122.6 (3)	C9—C14—H14B	109.5
C2—C1—C6	122.0 (3)	H14A—C14—H14B	109.5
N1—C1—C6	115.3 (2)	C9—C14—H14C	109.5
C3—C2—C1	118.0 (3)	H14A—C14—H14C	109.5
C3—C2—H2	121.0	H14B—C14—H14C	109.5
C1—C2—H2	121.0	C10—C15—H15A	109.5
C2—C3—C4	120.9 (3)	C10—C15—H15B	109.5
C2—C3—H3	119.6	H15A—C15—H15B	109.5
C4—C3—H3	119.5	C10—C15—H15C	109.4
C3—C4—C5	120.7 (3)	H15A—C15—H15C	109.5
C3—C4—H4	119.8	H15B—C15—H15C	109.5
C5—C4—H4	119.6	O3—C16—O2	125.0 (3)
C6—C5—C4	120.3 (3)	O3—C16—C11	124.8 (3)
C6—C5—H5	119.9	O2—C16—C11	110.2 (3)
C4—C5—H5	119.8	O2—C17—C18	107.9 (3)
C5—C6—C1	118.1 (3)	O2—C17—H17A	110.2
C5—C6—C7	120.1 (3)	C18—C17—H17A	110.2
C1—C6—C7	121.8 (2)	O2—C17—H17B	110.1
C11—C7—C8	118.4 (3)	C18—C17—H17B	110.0
C11—C7—C6	120.8 (3)	H17A—C17—H17B	108.5
C8—C7—C6	120.8 (2)	C19—C18—C17	113.8 (4)
C9—C8—C7	119.0 (3)	C19—C18—C20	111.3 (4)
C9—C8—C12	121.5 (3)	C17—C18—C20	108.8 (4)
C7—C8—C12	119.3 (2)	C19—C18—H18	107.5
N2—C9—C8	122.1 (3)	C17—C18—H18	107.6
N2—C9—C14	114.9 (3)	C20—C18—H18	107.6
C8—C9—C14	122.9 (3)	C18—C19—H19A	109.4
N2—C10—C11	121.4 (3)	C18—C19—H19B	109.5
N2—C10—C15	116.5 (3)	H19A—C19—H19B	109.5
C11—C10—C15	122.1 (3)	C18—C19—H19C	109.6
C7—C11—C10	119.4 (3)	H19A—C19—H19C	109.5
C7—C11—C16	119.9 (3)	H19B—C19—H19C	109.5
C10—C11—C16	120.7 (3)	C18—C20—H20A	109.4
O4—C12—O5	123.1 (3)	C18—C20—H20B	109.3
O4—C12—C8	124.3 (3)	H20A—C20—H20B	109.5
O5—C12—C8	112.5 (2)	C18—C20—H20C	109.7
O5—C13—H13A	109.5	H20A—C20—H20C	109.5
O5—C13—H13B	109.5	H20B—C20—H20C	109.5
H13A—C13—H13B	109.5	O1—N1—C1	114.7 (3)
O5—C13—H13C	109.4	C10—N2—C9	119.6 (3)
H13A—C13—H13C	109.5	C16—O2—C17	116.4 (3)
H13B—C13—H13C	109.5	C12—O5—C13	116.7 (3)
C9—C14—H14A	109.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O1ⁱ	0.96	2.39	3.344 (5)	172
C14—H14B···O4ⁱⁱ	0.96	2.52	3.472 (5)	174

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₂O₅
M_r	370.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.1831 (4), 9.7819 (6), 15.0245 (9)
α, β, γ (°)	89.488 (3), 81.201 (3), 70.625 (3)
V (Å³)	983.19 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.42 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEX II CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.963, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5353, 3623, 2500
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.311, 1.01
No. of reflections	3623
No. of parameters	250
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.29

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
C13—H13B···O1ⁱ	0.96	2.39	3.344 (5)	172
C14—H14B···O4ⁱⁱ	0.96	2.52	3.472 (5)	174

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

Acknowledgements

We thank the Natural Science Foundation of China (Nos. 30901883, 20972189, 30600163), the Natural Science Foundation of Shannxi Province (No. 2008C274) and the Administration Traditional Chinese Medicine Foundation of Shannxi Province (No. jc46, zy16) for financial support.

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. 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

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Volume 66| Part 3| March 2010| Page o619

doi:10.1107/S1600536810005088

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

5-Methyl 3-(2-methyl­prop-3-yl) 2,6-di­methyl-4-(2-nitro­sophen­yl)pyridine-3,5-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-Methyl 3-(2-methylprop-3-yl) 2,6-dimethyl-4-(2-nitrosophenyl)pyridine-3,5-dicarboxylate