3-Isobutyl 5-methyl 2,6-dimethyl-4-(2-nitro-phen-yl)pyridine-3,5-dicarboxyl-ate.

The title nitro-phenyl pyridine compound, C(20)H(22)N(2)O(6) 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 inter-actions between symmetry-related mol-ecules>.

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 = 386.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.154

S = 1.01

3683 reflections

259 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H22N2O6	F(000) = 816
Mr = 386.40	Dx = 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

Bruker APEXII CCD diffractometer	3683 independent reflections
Radiation source: fine-focus sealed tube	2718 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
Tmin = 0.989, Tmax = 0.992	k = −20→16
10199 measured reflections	l = −17→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.090P)2 + 0.3869P] where P = (Fo2 + 2Fc2)/3
3683 reflections	(Δ/σ)max < 0.001
259 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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

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

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) ; (ii) ; (iii) .