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

The title compound, C(17)H(16)N(2)O(6), is a decomposition product of the hypertension drug nifedipine [systematic name: dimethyl 2,6-dimethyl-4-(2-nitro-phen-yl)-1,4-dihydro-pyridine-3,5-dicarboxyl-ate]. The dihedral angle between the nitro-sophenyl ring and the pyridine ring is 67.1 (5)°.

Related literature

For the calcium antagonistic activity of compounds of the 1,4-dihydro­pyridine class, which inhibit the influx of Ca2+ ions through plasma membrane channels, see: Núnez-Vergara et al. (1994 ▶) and for their current use in the treatment of a variety of cardiovascular disorders such as angina and hypertension, see: Triggle et al. (1989 ▶); Hurwitz et al. (1991 ▶). For general background to derivatives of the dihydropyridine calcium channel blockers nifedipine [3,5-dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate] and nisoldpine [isobutyl methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate], see: Chen et al. (2010 ▶); Rowan & Holt (1996 ▶, 1997a ▶,b ▶); Schultheiss et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H16N2O6

M = 344.32

Triclinic,

a = 7.578 (4) Å

b = 8.141 (4) Å

c = 14.235 (9) Å

α = 103.32 (2)°

β = 93.75 (5)°

γ = 105.39 (3)°

V = 816.4 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.979, T max = 0.987

8658 measured reflections

3843 independent reflections

2247 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.03

3843 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku, 2005 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039626/qm2031sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039626/qm2031Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039626/qm2031Isup3.cml

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

C17H16N2O6	Z = 2
Mr = 344.32	F(000) = 360
Triclinic, P1	Dx = 1.401 Mg m−3
a = 7.578 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.141 (4) Å	Cell parameters from 2919 reflections
c = 14.235 (9) Å	θ = 1.5–28.0°
α = 103.32 (2)°	µ = 0.11 mm−1
β = 93.75 (5)°	T = 298 K
γ = 105.39 (3)°	Prism, yellow
V = 816.4 (8) Å3	0.20 × 0.18 × 0.12 mm

Rigaku Saturn724 CCD diffractometer	3843 independent reflections
Radiation source: rotating anode	2247 reflections with I > 2σ(I)
multilayer	Rint = 0.047
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 1.5°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.979, Tmax = 0.987	l = −18→17
8658 measured reflections

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(Fo2) + (0.028P)2] where P = (Fo2 + 2Fc2)/3
3843 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.29 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
O1	0.76803 (15)	0.93198 (15)	0.92024 (8)	0.0333 (3)
O2	0.84798 (13)	0.68996 (14)	0.85050 (7)	0.0240 (3)
O3	0.40716 (15)	0.78829 (15)	0.70787 (8)	0.0344 (3)
O4	0.63979 (19)	0.91761 (16)	0.64507 (10)	0.0520 (4)
O5	0.13443 (14)	0.30250 (15)	0.61801 (7)	0.0279 (3)
O6	0.18628 (14)	0.11367 (14)	0.70271 (7)	0.0259 (3)
N1	0.26875 (17)	0.55143 (17)	0.95102 (9)	0.0218 (3)
N2	0.54570 (19)	0.78817 (18)	0.66853 (9)	0.0283 (3)
C1	0.5124 (2)	0.7905 (2)	1.05399 (10)	0.0256 (4)
H1A	0.4799	0.8996	1.0549	0.038*
H1B	0.6471	0.8165	1.0651	0.038*
H1C	0.4582	0.7401	1.1054	0.038*
C2	0.4386 (2)	0.6606 (2)	0.95644 (10)	0.0200 (3)
C3	0.53855 (19)	0.65051 (19)	0.87679 (10)	0.0184 (3)
C4	0.45649 (19)	0.52477 (19)	0.78913 (10)	0.0175 (3)
C5	0.2806 (2)	0.4125 (2)	0.78490 (10)	0.0188 (3)
C6	0.1892 (2)	0.4295 (2)	0.86757 (11)	0.0200 (3)
C7	−0.0011 (2)	0.3140 (2)	0.86810 (11)	0.0278 (4)
H7A	0.0077	0.2160	0.8954	0.042*
H7B	−0.0653	0.2675	0.8013	0.042*
H7C	−0.0701	0.3832	0.9080	0.042*
C8	0.7278 (2)	0.7743 (2)	0.88633 (11)	0.0214 (3)
C9	1.0316 (2)	0.8018 (2)	0.84997 (12)	0.0297 (4)
H9A	1.0228	0.8948	0.8183	0.045*
H9B	1.1038	0.7310	0.8141	0.045*
H9C	1.0925	0.8554	0.9171	0.045*
C10	0.55534 (18)	0.50220 (19)	0.70104 (10)	0.0176 (3)
C11	0.6085 (2)	0.3487 (2)	0.67264 (10)	0.0226 (4)
H11	0.5774	0.2612	0.7077	0.027*
C12	0.7059 (2)	0.3213 (2)	0.59432 (11)	0.0267 (4)
H12	0.7401	0.2154	0.5759	0.032*
C13	0.7538 (2)	0.4482 (2)	0.54255 (11)	0.0263 (4)
H13	0.8218	0.4296	0.4893	0.032*
C14	0.7024 (2)	0.6014 (2)	0.56854 (11)	0.0237 (4)
H14	0.7342	0.6887	0.5334	0.028*
C15	0.60384 (19)	0.6254 (2)	0.64663 (10)	0.0202 (3)
C16	0.19127 (19)	0.2747 (2)	0.69257 (11)	0.0200 (3)
C17	0.1122 (2)	−0.0294 (2)	0.61593 (12)	0.0364 (4)
H17A	−0.0139	−0.0318	0.5937	0.055*
H17B	0.1105	−0.1415	0.6307	0.055*
H17C	0.1898	−0.0116	0.5646	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0287 (7)	0.0182 (6)	0.0483 (8)	0.0042 (5)	0.0079 (5)	0.0014 (6)
O2	0.0200 (6)	0.0216 (6)	0.0293 (6)	0.0058 (5)	0.0056 (5)	0.0041 (5)
O3	0.0382 (7)	0.0388 (8)	0.0381 (7)	0.0221 (6)	0.0167 (6)	0.0170 (6)
O4	0.0680 (10)	0.0273 (8)	0.0727 (10)	0.0148 (7)	0.0355 (8)	0.0278 (8)
O5	0.0279 (6)	0.0343 (7)	0.0211 (6)	0.0059 (5)	0.0023 (5)	0.0102 (5)
O6	0.0320 (6)	0.0194 (6)	0.0223 (6)	0.0061 (5)	−0.0008 (5)	0.0004 (5)
N1	0.0245 (7)	0.0220 (7)	0.0214 (7)	0.0086 (6)	0.0074 (5)	0.0072 (6)
N2	0.0376 (9)	0.0251 (8)	0.0255 (8)	0.0098 (7)	0.0069 (6)	0.0111 (7)
C1	0.0318 (9)	0.0260 (9)	0.0212 (8)	0.0119 (8)	0.0040 (7)	0.0058 (7)
C2	0.0248 (8)	0.0195 (8)	0.0188 (8)	0.0109 (7)	0.0036 (6)	0.0057 (7)
C3	0.0200 (8)	0.0168 (8)	0.0211 (8)	0.0080 (7)	0.0040 (6)	0.0065 (7)
C4	0.0205 (8)	0.0173 (8)	0.0188 (8)	0.0094 (7)	0.0062 (6)	0.0072 (7)
C5	0.0210 (8)	0.0190 (8)	0.0188 (8)	0.0077 (7)	0.0052 (6)	0.0066 (7)
C6	0.0222 (8)	0.0190 (8)	0.0217 (8)	0.0082 (7)	0.0065 (6)	0.0072 (7)
C7	0.0247 (9)	0.0281 (10)	0.0287 (9)	0.0048 (8)	0.0119 (7)	0.0045 (8)
C8	0.0248 (8)	0.0223 (9)	0.0176 (8)	0.0074 (7)	0.0039 (6)	0.0051 (7)
C9	0.0192 (8)	0.0312 (10)	0.0363 (10)	0.0029 (7)	0.0059 (7)	0.0085 (8)
C10	0.0131 (7)	0.0195 (8)	0.0170 (8)	0.0008 (6)	0.0016 (6)	0.0034 (6)
C11	0.0219 (8)	0.0213 (9)	0.0241 (9)	0.0054 (7)	0.0041 (7)	0.0055 (7)
C12	0.0244 (9)	0.0258 (9)	0.0285 (9)	0.0101 (8)	0.0054 (7)	0.0005 (8)
C13	0.0201 (8)	0.0334 (10)	0.0210 (9)	0.0047 (8)	0.0067 (6)	0.0012 (8)
C14	0.0207 (8)	0.0276 (9)	0.0194 (8)	0.0001 (7)	0.0039 (6)	0.0071 (7)
C15	0.0185 (8)	0.0193 (8)	0.0207 (8)	0.0034 (7)	0.0023 (6)	0.0036 (7)
C16	0.0142 (7)	0.0234 (9)	0.0231 (9)	0.0041 (7)	0.0080 (6)	0.0073 (7)
C17	0.0424 (11)	0.0262 (10)	0.0303 (10)	0.0072 (9)	−0.0033 (8)	−0.0074 (8)

O1—C8	1.2086 (18)	C5—C16	1.498 (2)
O2—C8	1.3392 (18)	C6—C7	1.500 (2)
O2—C9	1.4485 (18)	C7—H7A	0.9800
O3—N2	1.2218 (16)	C7—H7B	0.9800
O4—N2	1.2349 (16)	C7—H7C	0.9800
O5—C16	1.2107 (18)	C9—H9A	0.9800
O6—C16	1.3427 (19)	C9—H9B	0.9800
O6—C17	1.4481 (19)	C9—H9C	0.9800
N1—C2	1.342 (2)	C10—C15	1.393 (2)
N1—C6	1.344 (2)	C10—C11	1.394 (2)
N2—C15	1.478 (2)	C11—C12	1.385 (2)
C1—C2	1.506 (2)	C11—H11	0.9500
C1—H1A	0.9800	C12—C13	1.388 (2)
C1—H1B	0.9800	C12—H12	0.9500
C1—H1C	0.9800	C13—C14	1.381 (2)
C2—C3	1.403 (2)	C13—H13	0.9500
C3—C4	1.401 (2)	C14—C15	1.385 (2)
C3—C8	1.495 (2)	C14—H14	0.9500
C4—C5	1.390 (2)	C17—H17A	0.9800
C4—C10	1.502 (2)	C17—H17B	0.9800
C5—C6	1.402 (2)	C17—H17C	0.9800
C8—O2—C9	115.40 (13)	O2—C8—C3	111.74 (14)
C16—O6—C17	115.28 (12)	O2—C9—H9A	109.5
C2—N1—C6	120.11 (13)	O2—C9—H9B	109.5
O3—N2—O4	123.19 (15)	H9A—C9—H9B	109.5
O3—N2—C15	118.96 (13)	O2—C9—H9C	109.5
O4—N2—C15	117.85 (14)	H9A—C9—H9C	109.5
C2—C1—H1A	109.5	H9B—C9—H9C	109.5
C2—C1—H1B	109.5	C15—C10—C11	116.86 (13)
H1A—C1—H1B	109.5	C15—C10—C4	125.17 (14)
C2—C1—H1C	109.5	C11—C10—C4	117.94 (13)
H1A—C1—H1C	109.5	C12—C11—C10	121.28 (15)
H1B—C1—H1C	109.5	C12—C11—H11	119.4
N1—C2—C3	121.69 (15)	C10—C11—H11	119.4
N1—C2—C1	114.91 (13)	C11—C12—C13	120.22 (15)
C3—C2—C1	123.39 (14)	C11—C12—H12	119.9
C4—C3—C2	118.72 (14)	C13—C12—H12	119.9
C4—C3—C8	121.45 (13)	C14—C13—C12	119.93 (14)
C2—C3—C8	119.83 (14)	C14—C13—H13	120.0
C5—C4—C3	118.81 (13)	C12—C13—H13	120.0
C5—C4—C10	118.94 (14)	C13—C14—C15	118.90 (15)
C3—C4—C10	122.20 (13)	C13—C14—H14	120.5
C4—C5—C6	119.36 (14)	C15—C14—H14	120.5
C4—C5—C16	119.84 (13)	C14—C15—C10	122.80 (15)
C6—C5—C16	120.80 (14)	C14—C15—N2	116.56 (14)
N1—C6—C5	121.30 (14)	C10—C15—N2	120.61 (13)
N1—C6—C7	116.40 (13)	O5—C16—O6	123.94 (15)
C5—C6—C7	122.30 (14)	O5—C16—C5	125.59 (15)
C6—C7—H7A	109.5	O6—C16—C5	110.45 (13)
C6—C7—H7B	109.5	O6—C17—H17A	109.5
H7A—C7—H7B	109.5	O6—C17—H17B	109.5
C6—C7—H7C	109.5	H17A—C17—H17B	109.5
H7A—C7—H7C	109.5	O6—C17—H17C	109.5
H7B—C7—H7C	109.5	H17A—C17—H17C	109.5
O1—C8—O2	123.61 (15)	H17B—C17—H17C	109.5
O1—C8—C3	124.63 (14)
C6—N1—C2—C3	−0.6 (2)	C5—C4—C10—C15	115.28 (17)
C6—N1—C2—C1	−179.75 (12)	C3—C4—C10—C15	−67.4 (2)
N1—C2—C3—C4	1.1 (2)	C5—C4—C10—C11	−66.86 (18)
C1—C2—C3—C4	−179.85 (13)	C3—C4—C10—C11	110.45 (17)
N1—C2—C3—C8	−179.70 (13)	C15—C10—C11—C12	0.4 (2)
C1—C2—C3—C8	−0.7 (2)	C4—C10—C11—C12	−177.67 (14)
C2—C3—C4—C5	−1.2 (2)	C10—C11—C12—C13	0.4 (2)
C8—C3—C4—C5	179.60 (13)	C11—C12—C13—C14	−0.7 (2)
C2—C3—C4—C10	−178.56 (13)	C12—C13—C14—C15	0.2 (2)
C8—C3—C4—C10	2.3 (2)	C13—C14—C15—C10	0.6 (2)
C3—C4—C5—C6	0.9 (2)	C13—C14—C15—N2	−177.47 (13)
C10—C4—C5—C6	178.33 (13)	C11—C10—C15—C14	−0.9 (2)
C3—C4—C5—C16	−178.88 (13)	C4—C10—C15—C14	176.99 (14)
C10—C4—C5—C16	−1.5 (2)	C11—C10—C15—N2	177.12 (13)
C2—N1—C6—C5	0.3 (2)	C4—C10—C15—N2	−5.0 (2)
C2—N1—C6—C7	−179.65 (13)	O3—N2—C15—C14	152.38 (14)
C4—C5—C6—N1	−0.5 (2)	O4—N2—C15—C14	−27.0 (2)
C16—C5—C6—N1	179.35 (13)	O3—N2—C15—C10	−25.7 (2)
C4—C5—C6—C7	179.50 (13)	O4—N2—C15—C10	154.89 (15)
C16—C5—C6—C7	−0.7 (2)	C17—O6—C16—O5	1.9 (2)
C9—O2—C8—O1	−3.1 (2)	C17—O6—C16—C5	−176.59 (11)
C9—O2—C8—C3	175.45 (12)	C4—C5—C16—O5	−70.6 (2)
C4—C3—C8—O1	131.12 (17)	C6—C5—C16—O5	109.63 (18)
C2—C3—C8—O1	−48.0 (2)	C4—C5—C16—O6	107.95 (15)
C4—C3—C8—O2	−47.44 (18)	C6—C5—C16—O6	−71.86 (17)
C2—C3—C8—O2	133.40 (14)