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

In the title compound, C(18)H(17)Cl(2)NO(4), 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 = 382.23

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.153

S = 1.00

4268 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.26 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, global. DOI: 10.1107/S1600536810003235/pk2222sup1.cif

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

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

C18H17Cl2NO4	F(000) = 1584
Mr = 382.23	Dx = 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

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

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(Fo2) + (0.056P)2 + 2.0434P] where P = (Fo2 + 2Fc2)/3
4268 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.26 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	0.6713 (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)

	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)

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)

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

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) ; (ii) ; (iii) .