3-Ethyl 5-methyl 4-(2,3-dichloro­phen­yl)-2,6-dimethyl­pyridine-3,5-dicarboxyl­ate

Luo, J.; Chen, H.; Wang, Q.-F.; Liu, H.-J.

doi:10.1107/S1600536810003235

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o538

doi:10.1107/S1600536810003235

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3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Jing Luo,^a Hui Chen,^b Qiao-Feng Wang ^b and Hai-Jing Liu ^a ^*

^aShaanXi Institute For Food And Drug Control, Zhuque Road 431, 710061 Xi-An, People's Republic of China, and ^bDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
^*Correspondence e-mail: liuhaijing1@163.com

(Received 16 December 2009; accepted 26 January 2010; online 6 February 2010)

In the title compound, C₁₈H₁₇Cl₂NO₄, an oxidation product of felodipine, the dihedral angle between the benzene and pyridine rings is 75.3 (4)°. The crystal structure is stabilized by intermolecular C—H⋯O interactions.

Related literature

For related structures, see: Baranda et al. (2004 ); Che et al. (2004 ); Won et al. (2005 ); Xu et al. (1995 ). For felodipine derivatives as calcium channel blockers with vasodilator properties, see: Ferrari et al. (2005 ); Qin et al. (1995 ); Marciniec et al. (2002 ).

Experimental

Crystal data

C₁₈H₁₇Cl₂NO₄
M_r = 382.23
Orthorhombic, P b c a
a = 14.3179 (6) Å
b = 15.5045 (7) Å
c = 16.9664 (8) Å
V = 3766.4 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.12 × 0.09 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.957, T_max = 0.971
21810 measured reflections
4268 independent reflections
2268 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.153
S = 1.00
4268 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.55	3.303 (4)	139
C16—H16C⋯O1ⁱⁱ	0.96	2.67	3.328 (5)	126
C17—H17B⋯O4ⁱⁱⁱ	0.97	2.55	3.247 (4)	129
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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 I, global. DOI: 10.1107/S1600536810003235/pk2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003235/pk2222Isup2.hkl

checkCIF report

Comment top

Felodipine is a calcium channel blocker with vasodilator properties. It is used in several commercial preparations for treatment of hypertension (Marciniec et al., 2002). It has been the subject of many analytical chemical investigations. Regulations on the purity profile of bulk drug substances require determination of levels of impurities such as the title compound, which is an oxidation product of felodipine.

The molecular structure is shown in Fig 1. The dihedral angle between the phenyl ring and the pyridine ring is 75.3 (4)°. The crystal structure is stabilized by van der Waals interactions.

Related literature top

For related structures, see: Baranda et al. (2004); Che et al. (2004); Won et al. (2005); Xu et al. (1995). For felodipine derivatives as calcium channel blockers with vasodilator properties, see: Ferrari et al. (2005); Qin et al. (1995); Marciniec et al. (2002).

Experimental top

A mixture of 5 g felodipine and 50 mL 50% sulfuric acid (50%, v/v) was heated under reflux for 30 min, then cooled to room temperature and saturated sodium hydroxide was added slowly until the solution was neutral. The mixture was then extracted with 3×100 ml CHCl₃ and the combined organic layers were dried over Na₂SO4 before solvent removal. The product was purified by chromatography on silica gel with 1:1 EtOAc / hexanes as eluent.

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 (I). Displacement ellipsoids are drawn at the 30% probability level.

3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate top

Crystal data top

C₁₈H₁₇Cl₂NO₄	F(000) = 1584
M_r = 382.23	D_x = 1.348 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2869 reflections
a = 14.3179 (6) Å	θ = 2.4–20.2°
b = 15.5045 (7) Å	µ = 0.37 mm⁻¹
c = 16.9664 (8) Å	T = 296 K
V = 3766.4 (3) Å³	Block, colorless
Z = 8	0.12 × 0.09 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	4268 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→11
T_min = 0.957, T_max = 0.971	k = −19→18
21810 measured reflections	l = −21→21

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.056P)² + 2.0434P] where P = (F_o² + 2F_c²)/3
4268 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₁₇Cl₂NO₄	V = 3766.4 (3) Å³
M_r = 382.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.3179 (6) Å	µ = 0.37 mm⁻¹
b = 15.5045 (7) Å	T = 296 K
c = 16.9664 (8) Å	0.12 × 0.09 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	4268 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2268 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.971	R_int = 0.054
21810 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.00	Δρ_max = 0.36 e Å⁻³
4268 reflections	Δρ_min = −0.26 e Å⁻³
230 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	0.6713 (2)	0.16190 (18)	0.34902 (17)	0.0502 (7)
C2	0.6979 (2)	0.08675 (19)	0.30988 (19)	0.0616 (8)
C3	0.7775 (3)	0.0859 (2)	0.2636 (2)	0.0718 (10)
H3	0.7955	0.0357	0.2378	0.086*
C4	0.8295 (2)	0.1596 (2)	0.2559 (2)	0.0715 (9)
H4	0.8832	0.1591	0.2251	0.086*
C5	0.8034 (2)	0.2339 (2)	0.29326 (18)	0.0584 (8)
H5	0.8393	0.2834	0.2872	0.070*
C6	0.72405 (18)	0.23629 (18)	0.33994 (16)	0.0462 (7)
C7	0.69755 (18)	0.31818 (17)	0.38064 (16)	0.0448 (6)
C8	0.74662 (19)	0.34553 (19)	0.44663 (16)	0.0504 (7)
C9	0.7225 (2)	0.4235 (2)	0.48194 (18)	0.0608 (8)
C10	0.6020 (2)	0.44520 (19)	0.39427 (18)	0.0542 (7)
C11	0.62486 (18)	0.37031 (18)	0.35304 (16)	0.0460 (7)
C12	0.5729 (2)	0.34657 (18)	0.28006 (18)	0.0519 (7)
C13	0.8256 (2)	0.2937 (2)	0.47870 (17)	0.0594 (8)
C14	0.5231 (2)	0.5037 (2)	0.3710 (2)	0.0731 (10)
H14A	0.4807	0.5098	0.4145	0.110*
H14B	0.4907	0.4796	0.3267	0.110*
H14C	0.5476	0.5593	0.3570	0.110*
C15	0.7767 (3)	0.4590 (3)	0.5511 (2)	0.0977 (13)
H15A	0.8121	0.5084	0.5344	0.147*
H15B	0.8183	0.4155	0.5707	0.147*
H15C	0.7340	0.4757	0.5920	0.147*
C16	0.8683 (3)	0.1748 (3)	0.5567 (3)	0.1154 (17)
H16A	0.9022	0.1437	0.5170	0.173*
H16B	0.8388	0.1347	0.5919	0.173*
H16C	0.9106	0.2107	0.5858	0.173*
C17	0.5886 (3)	0.3220 (3)	0.1420 (2)	0.0806 (11)
H17A	0.6231	0.3485	0.0992	0.097*
H17B	0.5241	0.3409	0.1383	0.097*
C18	0.5928 (3)	0.2273 (3)	0.1341 (2)	0.0997 (14)
H18A	0.6557	0.2081	0.1429	0.150*
H18B	0.5734	0.2110	0.0821	0.150*
H18C	0.5522	0.2012	0.1723	0.150*
Cl1	0.57453 (6)	0.16217 (6)	0.40985 (6)	0.0735 (3)
Cl2	0.63272 (8)	−0.00639 (6)	0.31910 (7)	0.0982 (4)
N1	0.65082 (19)	0.47100 (17)	0.45730 (15)	0.0630 (7)
O1	0.49233 (15)	0.32839 (17)	0.27743 (14)	0.0830 (8)
O2	0.62809 (14)	0.35000 (15)	0.21758 (12)	0.0665 (6)
O3	0.79723 (16)	0.22840 (16)	0.51927 (17)	0.0860 (8)
O4	0.90563 (18)	0.3137 (2)	0.47082 (18)	0.1162 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0476 (15)	0.0505 (17)	0.0526 (17)	0.0011 (14)	−0.0078 (13)	0.0058 (14)
C2	0.070 (2)	0.0493 (18)	0.065 (2)	0.0015 (16)	−0.0240 (17)	0.0022 (15)
C3	0.085 (3)	0.067 (2)	0.063 (2)	0.028 (2)	−0.0124 (19)	−0.0119 (18)
C4	0.068 (2)	0.086 (3)	0.061 (2)	0.019 (2)	0.0066 (17)	−0.0047 (19)
C5	0.0483 (17)	0.066 (2)	0.061 (2)	0.0025 (15)	0.0045 (15)	0.0006 (16)
C6	0.0410 (15)	0.0518 (16)	0.0458 (16)	0.0036 (13)	−0.0063 (12)	−0.0002 (13)
C7	0.0410 (15)	0.0482 (16)	0.0452 (16)	−0.0027 (13)	0.0025 (12)	0.0009 (12)
C8	0.0471 (15)	0.0592 (18)	0.0449 (16)	−0.0013 (14)	−0.0014 (14)	0.0008 (14)
C9	0.069 (2)	0.065 (2)	0.0484 (18)	−0.0016 (17)	−0.0028 (15)	−0.0051 (15)
C10	0.0550 (18)	0.0545 (18)	0.0532 (19)	0.0024 (14)	0.0056 (14)	0.0058 (14)
C11	0.0452 (15)	0.0486 (16)	0.0443 (16)	−0.0032 (13)	0.0005 (12)	0.0035 (13)
C12	0.0454 (17)	0.0539 (17)	0.0565 (19)	0.0012 (14)	−0.0054 (14)	0.0057 (14)
C13	0.054 (2)	0.079 (2)	0.0446 (17)	0.0017 (17)	−0.0055 (15)	−0.0050 (16)
C14	0.072 (2)	0.062 (2)	0.085 (3)	0.0173 (17)	−0.0004 (19)	−0.0003 (18)
C15	0.122 (3)	0.098 (3)	0.074 (3)	0.013 (3)	−0.034 (2)	−0.033 (2)
C16	0.099 (3)	0.072 (3)	0.175 (5)	0.014 (2)	−0.065 (3)	0.022 (3)
C17	0.088 (3)	0.103 (3)	0.051 (2)	−0.009 (2)	−0.0154 (18)	−0.0036 (19)
C18	0.113 (3)	0.103 (3)	0.083 (3)	0.000 (3)	−0.019 (2)	−0.022 (2)
Cl1	0.0591 (5)	0.0707 (6)	0.0907 (6)	−0.0108 (4)	0.0126 (4)	0.0090 (5)
Cl2	0.1146 (8)	0.0497 (5)	0.1304 (10)	−0.0090 (5)	−0.0369 (7)	0.0011 (5)
N1	0.0763 (18)	0.0573 (16)	0.0555 (17)	0.0072 (14)	−0.0004 (14)	−0.0067 (13)
O1	0.0480 (13)	0.125 (2)	0.0764 (17)	−0.0154 (14)	−0.0082 (11)	−0.0051 (15)
O2	0.0584 (13)	0.0900 (17)	0.0512 (13)	−0.0115 (11)	−0.0062 (10)	−0.0020 (11)
O3	0.0682 (15)	0.0638 (15)	0.126 (2)	−0.0021 (12)	−0.0318 (15)	0.0242 (15)
O4	0.0533 (16)	0.182 (3)	0.114 (2)	0.0082 (18)	−0.0036 (15)	0.057 (2)

Geometric parameters (Å, º) top

C1—C6	1.387 (4)	C12—O1	1.188 (3)
C1—C2	1.394 (4)	C12—O2	1.323 (3)
C1—Cl1	1.728 (3)	C13—O4	1.194 (4)
C2—C3	1.384 (5)	C13—O3	1.290 (4)
C2—Cl2	1.726 (3)	C14—H14A	0.9602
C3—C4	1.371 (5)	C14—H14B	0.9602
C3—H3	0.9300	C14—H14C	0.9602
C4—C5	1.367 (4)	C15—H15A	0.9601
C4—H4	0.9300	C15—H15B	0.9601
C5—C6	1.385 (4)	C15—H15C	0.9601
C5—H5	0.9300	C16—O3	1.459 (4)
C6—C7	1.494 (4)	C16—H16A	0.9600
C7—C11	1.398 (4)	C16—H16B	0.9600
C7—C8	1.388 (4)	C16—H16C	0.9600
C8—C9	1.393 (4)	C17—O2	1.467 (4)
C8—C13	1.490 (4)	C17—C18	1.476 (5)
C9—N1	1.331 (4)	C17—H17A	0.9700
C9—C15	1.510 (4)	C17—H17B	0.9700
C10—N1	1.339 (4)	C18—H18A	0.9600
C10—C11	1.395 (4)	C18—H18B	0.9600
C10—C14	1.501 (4)	C18—H18C	0.9600
C11—C12	1.491 (4)

C6—C1—C2	119.6 (3)	O4—C13—O3	124.5 (3)
C6—C1—Cl1	120.1 (2)	O4—C13—C8	123.2 (3)
C2—C1—Cl1	120.4 (2)	O3—C13—C8	112.2 (3)
C3—C2—C1	120.2 (3)	C10—C14—H14A	109.5
C3—C2—Cl2	119.2 (3)	C10—C14—H14B	109.5
C1—C2—Cl2	120.6 (3)	H14A—C14—H14B	109.5
C4—C3—C2	119.6 (3)	C10—C14—H14C	109.5
C4—C3—H3	120.2	H14A—C14—H14C	109.5
C2—C3—H3	120.2	H14B—C14—H14C	109.5
C3—C4—C5	120.6 (3)	C9—C15—H15A	109.5
C3—C4—H4	119.7	C9—C15—H15B	109.5
C5—C4—H4	119.7	H15A—C15—H15B	109.5
C4—C5—C6	120.8 (3)	C9—C15—H15C	109.5
C4—C5—H5	119.6	H15A—C15—H15C	109.5
C6—C5—H5	119.6	H15B—C15—H15C	109.5
C5—C6—C1	119.2 (3)	O3—C16—H16A	109.5
C5—C6—C7	119.7 (3)	O3—C16—H16B	109.5
C1—C6—C7	121.1 (2)	H16A—C16—H16B	109.5
C11—C7—C8	118.1 (3)	O3—C16—H16C	109.5
C11—C7—C6	121.7 (2)	H16A—C16—H16C	109.5
C8—C7—C6	120.2 (2)	H16B—C16—H16C	109.5
C9—C8—C7	119.1 (3)	O2—C17—C18	110.9 (3)
C9—C8—C13	119.9 (3)	O2—C17—H17A	109.5
C7—C8—C13	120.9 (3)	C18—C17—H17A	109.5
N1—C9—C8	122.4 (3)	O2—C17—H17B	109.5
N1—C9—C15	116.0 (3)	C18—C17—H17B	109.4
C8—C9—C15	121.5 (3)	H17A—C17—H17B	108.0
N1—C10—C11	121.8 (3)	C17—C18—H18A	109.5
N1—C10—C14	114.9 (3)	C17—C18—H18B	109.5
C11—C10—C14	123.3 (3)	H18A—C18—H18B	109.5
C7—C11—C10	119.2 (3)	C17—C18—H18C	109.5
C7—C11—C12	120.5 (3)	H18A—C18—H18C	109.5
C10—C11—C12	120.3 (3)	H18B—C18—H18C	109.5
O1—C12—O2	124.0 (3)	C9—N1—C10	119.3 (3)
O1—C12—C11	125.1 (3)	C12—O2—C17	117.3 (2)
O2—C12—C11	110.9 (2)	C13—O3—C16	117.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.55	3.303 (4)	139
C16—H16C···O1ⁱⁱ	0.96	2.67	3.328 (5)	126
C17—H17B···O4ⁱⁱⁱ	0.97	2.55	3.247 (4)	129

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇Cl₂NO₄
M_r	382.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	14.3179 (6), 15.5045 (7), 16.9664 (8)
V (Å³)	3766.4 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.12 × 0.09 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.957, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	21810, 4268, 2268
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.153, 1.00
No. of reflections	4268
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.26

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
C5—H5···O1ⁱ	0.93	2.55	3.303 (4)	138.5
C16—H16C···O1ⁱⁱ	0.96	2.67000	3.328 (5)	126.00
C17—H17B···O4ⁱⁱⁱ	0.97	2.55	3.247 (4)	129.00

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

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

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Volume 66| Part 3| March 2010| Page o538

doi:10.1107/S1600536810003235

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

3-Ethyl 5-methyl 4-(2,3-di­chloro­phen­yl)-2,6-di­methyl­pyridine-3,5-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate