Dimethyl 1,4-dihydro-4-(4-methoxy­phen­yl)-2,6-dimethyl­pyridine-3,5-dicarboxyl­ate

Loh, W.-S.; Fun, H.-K.; Reddy, B.P.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536810004940

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o587-o588

doi:10.1107/S1600536810004940

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Dimethyl 1,4-dihydro-4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Wan-Sin Loh,^a ‡ Hoong-Kun Fun,^a ^*§ B. Palakshi Reddy,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 29 January 2010; accepted 8 February 2010; online 13 February 2010)

In the title compound, C₁₈H₂₁NO₅, the dihydropyridine ring adopts a flattened-boat conformation and its planar part forms a dihedral angle of 84.60 (2)° with the benzene ring. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds result in the formation of zigzag layers parallel to (001). These layers are interconnected via C—H⋯π interactions.

Related literature

For the synthesis, see: Rathore et al. (2009 ). For general background and applications of 1,4-dihydropyridine derivatives, see: Bocker & Guengerich (1986 ); Cooper et al. (1992 ); Gaudio et al. (1994 ); Gordeev et al. (1996 ); Sunkel et al. (1992 ); Vo et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Fun et al. (2009a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₂₁NO₅
M_r = 331.36
Triclinic, $[P \overline 1]$
a = 7.4106 (3) Å
b = 9.5715 (5) Å
c = 11.7771 (6) Å
α = 83.029 (1)°
β = 83.834 (1)°
γ = 77.424 (1)°
V = 806.46 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.35 × 0.34 × 0.24 mm

Data collection

Bruker SMART APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.966, T_max = 0.976
19600 measured reflections
4664 independent reflections
4319 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.110
S = 1.05
4664 reflections
226 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O4ⁱ	0.87 (2)	2.23 (2)	3.0906 (10)	169 (1)
C14—H14A⋯O1ⁱⁱ	0.96	2.54	3.4631 (13)	162
C18—H18B⋯O4ⁱ	0.96	2.56	3.4558 (12)	156
C12—H12B⋯Cg1ⁱⁱⁱ	0.96	2.79	3.6549 (11)	151
Symmetry codes: (i) x+1, y, z; (ii) x+1, y-1, z; (iii) -x+1, -y+1, -z.

Data collection: APEX DUO (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004940/ci5029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004940/ci5029Isup2.hkl

checkCIF report

Comment top

Hantzsch 1,4-dihydropyridines (1,4-DHPS) are biologically active compounds which include various vasodilator, antihypertensive, bronchodilator, heptaprotective, antitumor, antimutagenic, geroprotective and antidiabetic agents (Gaudio et al., 1994). Nifedipine, nitrendipine and nimodipine have been used commercially as calcium channel blockers (Bocker & Guengerich, 1986; Gordeev et al., 1996). For the treatment of congestive heart failure a number of DHP calcium antagonists have been introduced (Sunkel et al., 1992; Vo et al., 1995). Some DHPs have also been introduced as neuroprotectant and cognition enhancers. In addition, a number of DHPs with platelet anti-aggregatory activity have also been discovered (Cooper et al., 1992).

In the title compound (Fig. 1), the 1,4-dihydropyridine ring (C7–C11/N1) adopts a flattened-boat conformation with puckering parameter Q = 0.2368 (9) Å; Θ = 72.8 (2)° and ϕ = 186.1 (2)° (Cremer & Pople, 1975). The C8–C11 plane forms a dihedral angle of 84.60 (2)° with the C1–C6 benzene ring. Bond lengths (Allen et al., 1987) and angles are within the normal range and are comparable to those in closely related structures (Fun et al., 2009a,b).

In the crystal packing (Fig. 2), intermolecular N1—H1N1···O4 and C18—H18B···O4 hydrogen bonds (Table 1) link pairs of neighbouring molecules to form chains along the [100] direction; the chains contain R₂¹(6) ring motifs (Bernstein et al., 1995). Intermolecular C14—H14A···O1 hydrogen bonds further interconnect these chains together to form zigzag layers parallel to the (001). The crystal structure is further stabilized by C—H···π interactions involving the C1–C6 benzene ring (centroid Cg1).

Related literature top

For the synthesis, see: Rathore et al. (2009). For general background and applications of 1,4-dihydropyridine derivatives, see: Bocker & Guengerich (1986); Cooper et al. (1992); Gaudio et al. (1994); Gordeev et al. (1996); Sunkel et al. (1992); Vo et al. (1995). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2009a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Dimethyl 1,4-dihydro-2,6-dimethyl-4-(4-methoxyphenyl)-3,5-pyridine dicarboxylate was prepared according to the Hantzsch pyridine synthesis (Rathore et al., 2009). A mixture of 4-methoxybenzaldehyde (10.0 mmol), methylacetoacetate (20.0 mmol) and ammonium acetate (10.0 mmol) was heated at 353 K for 2 h (monitored by TLC). After the completion of the reaction, the mixture was cooled to room temperature and it was kept for 24 h to get a solid product. The solid formed was washed using diethyl ether. The washed solid was collected separately and the liquid kept for solidification. The purity of the crude product was checked through TLC and recrystallized using acetone and ether.

Computing details top

Data collection: APEX DUO (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the c axis, showing R¹₂(6) ring motifs. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Dimethyl 1,4-dihydro-4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate top

Crystal data top

C₁₈H₂₁NO₅	Z = 2
M_r = 331.36	F(000) = 352
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4106 (3) Å	Cell parameters from 9874 reflections
b = 9.5715 (5) Å	θ = 2.8–37.5°
c = 11.7771 (6) Å	µ = 0.10 mm⁻¹
α = 83.029 (1)°	T = 100 K
β = 83.834 (1)°	Block, colourless
γ = 77.424 (1)°	0.35 × 0.34 × 0.24 mm
V = 806.46 (7) Å³

Data collection top

Bruker SMART APEX DUO CCD area-detector diffractometer	4664 independent reflections
Radiation source: fine-focus sealed tube	4319 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.966, T_max = 0.976	k = −13→13
19600 measured reflections	l = −15→16

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0628P)² + 0.2437P] where P = (F_o² + 2F_c²)/3
4664 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₂₁NO₅	γ = 77.424 (1)°
M_r = 331.36	V = 806.46 (7) Å³
Triclinic, P1	Z = 2
a = 7.4106 (3) Å	Mo Kα radiation
b = 9.5715 (5) Å	µ = 0.10 mm⁻¹
c = 11.7771 (6) Å	T = 100 K
α = 83.029 (1)°	0.35 × 0.34 × 0.24 mm
β = 83.834 (1)°

Data collection top

Bruker SMART APEX DUO CCD area-detector diffractometer	4664 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4319 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.976	R_int = 0.019
19600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.48 e Å⁻³
4664 reflections	Δρ_min = −0.22 e Å⁻³
226 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.19666 (9)	0.64176 (7)	0.02070 (6)	0.01872 (14)
O2	0.45751 (9)	−0.03547 (8)	0.19907 (6)	0.02053 (15)
O3	0.76827 (9)	−0.08374 (7)	0.16829 (6)	0.01754 (14)
O4	0.13686 (9)	0.26414 (7)	0.49736 (6)	0.01760 (14)
O5	0.29405 (9)	0.35204 (8)	0.61485 (6)	0.01934 (14)
N1	0.78947 (10)	0.17746 (8)	0.42720 (6)	0.01437 (14)
C1	0.22940 (12)	0.30263 (9)	0.19929 (7)	0.01528 (16)
H1A	0.1636	0.2291	0.2132	0.018*
C2	0.17064 (12)	0.41859 (9)	0.11955 (7)	0.01588 (16)
H2A	0.0667	0.4221	0.0806	0.019*
C3	0.26760 (11)	0.52967 (9)	0.09799 (7)	0.01404 (16)
C4	0.42555 (12)	0.52171 (9)	0.15453 (8)	0.01685 (17)
H4A	0.4930	0.5942	0.1393	0.020*
C5	0.48191 (12)	0.40434 (9)	0.23414 (8)	0.01621 (17)
H5A	0.5875	0.3997	0.2718	0.019*
C6	0.38473 (11)	0.29392 (9)	0.25892 (7)	0.01226 (15)
C7	0.44663 (11)	0.16962 (9)	0.34963 (7)	0.01211 (15)
H7A	0.3513	0.1114	0.3631	0.015*
C8	0.62773 (11)	0.07428 (8)	0.30836 (7)	0.01266 (15)
C9	0.79129 (11)	0.08547 (9)	0.34450 (7)	0.01310 (15)
C10	0.63106 (11)	0.23953 (9)	0.49133 (7)	0.01351 (15)
C11	0.46306 (11)	0.22785 (9)	0.46145 (7)	0.01275 (15)
C12	0.28140 (14)	0.76387 (10)	0.00644 (9)	0.02215 (19)
H12A	0.2151	0.8376	−0.0455	0.033*
H12B	0.4079	0.7363	−0.0243	0.033*
H12C	0.2782	0.7998	0.0794	0.033*
C13	0.60706 (12)	−0.01947 (9)	0.22266 (7)	0.01414 (16)
C14	0.74903 (14)	−0.16612 (11)	0.07708 (9)	0.02279 (19)
H14A	0.8698	−0.2091	0.0444	0.034*
H14B	0.6814	−0.1038	0.0188	0.034*
H14C	0.6831	−0.2403	0.1073	0.034*
C15	0.28484 (11)	0.28084 (9)	0.52454 (7)	0.01380 (16)
C16	0.11938 (13)	0.41561 (11)	0.67270 (8)	0.02036 (18)
H16A	0.1416	0.4659	0.7338	0.031*
H16B	0.0540	0.3414	0.7037	0.031*
H16C	0.0462	0.4819	0.6191	0.031*
C17	0.98251 (11)	0.00466 (9)	0.30817 (8)	0.01614 (16)
H17A	0.9862	−0.0969	0.3206	0.024*
H17B	1.0712	0.0281	0.3526	0.024*
H17C	1.0122	0.0312	0.2282	0.024*
C18	0.67039 (12)	0.31346 (10)	0.58865 (8)	0.01716 (17)
H18A	0.5985	0.4101	0.5848	0.026*
H18B	0.8000	0.3156	0.5830	0.026*
H18C	0.6379	0.2619	0.6604	0.026*
H1N1	0.895 (2)	0.1892 (17)	0.4467 (13)	0.030 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0186 (3)	0.0164 (3)	0.0206 (3)	−0.0040 (2)	−0.0063 (2)	0.0048 (2)
O2	0.0147 (3)	0.0233 (3)	0.0262 (3)	−0.0051 (2)	−0.0037 (2)	−0.0088 (3)
O3	0.0143 (3)	0.0177 (3)	0.0218 (3)	−0.0029 (2)	−0.0008 (2)	−0.0080 (2)
O4	0.0111 (3)	0.0237 (3)	0.0187 (3)	−0.0042 (2)	−0.0016 (2)	−0.0036 (2)
O5	0.0127 (3)	0.0272 (3)	0.0193 (3)	−0.0035 (2)	0.0003 (2)	−0.0099 (3)
N1	0.0095 (3)	0.0180 (3)	0.0168 (3)	−0.0037 (2)	−0.0026 (2)	−0.0036 (3)
C1	0.0140 (4)	0.0160 (4)	0.0171 (4)	−0.0055 (3)	−0.0041 (3)	0.0002 (3)
C2	0.0139 (4)	0.0177 (4)	0.0168 (4)	−0.0039 (3)	−0.0055 (3)	0.0001 (3)
C3	0.0140 (3)	0.0141 (3)	0.0131 (3)	−0.0013 (3)	−0.0014 (3)	−0.0005 (3)
C4	0.0166 (4)	0.0161 (4)	0.0192 (4)	−0.0068 (3)	−0.0043 (3)	0.0015 (3)
C5	0.0140 (4)	0.0178 (4)	0.0182 (4)	−0.0056 (3)	−0.0057 (3)	0.0009 (3)
C6	0.0111 (3)	0.0132 (3)	0.0125 (3)	−0.0021 (3)	−0.0014 (3)	−0.0017 (3)
C7	0.0098 (3)	0.0135 (3)	0.0133 (3)	−0.0027 (3)	−0.0021 (3)	−0.0010 (3)
C8	0.0117 (3)	0.0119 (3)	0.0144 (3)	−0.0025 (3)	−0.0016 (3)	−0.0010 (3)
C9	0.0120 (3)	0.0126 (3)	0.0146 (3)	−0.0029 (3)	−0.0010 (3)	−0.0003 (3)
C10	0.0124 (4)	0.0148 (3)	0.0134 (3)	−0.0028 (3)	−0.0021 (3)	−0.0006 (3)
C11	0.0109 (3)	0.0146 (3)	0.0128 (3)	−0.0028 (3)	−0.0012 (3)	−0.0010 (3)
C12	0.0258 (5)	0.0168 (4)	0.0238 (4)	−0.0066 (3)	−0.0043 (3)	0.0043 (3)
C13	0.0141 (4)	0.0123 (3)	0.0161 (4)	−0.0030 (3)	−0.0017 (3)	−0.0006 (3)
C14	0.0205 (4)	0.0232 (4)	0.0270 (5)	−0.0042 (3)	−0.0016 (3)	−0.0131 (4)
C15	0.0131 (3)	0.0148 (3)	0.0132 (3)	−0.0028 (3)	−0.0013 (3)	0.0000 (3)
C16	0.0149 (4)	0.0243 (4)	0.0218 (4)	−0.0022 (3)	0.0021 (3)	−0.0087 (3)
C17	0.0101 (3)	0.0161 (4)	0.0223 (4)	−0.0023 (3)	−0.0014 (3)	−0.0030 (3)
C18	0.0132 (4)	0.0221 (4)	0.0178 (4)	−0.0038 (3)	−0.0037 (3)	−0.0059 (3)

Geometric parameters (Å, º) top

O1—C3	1.3697 (10)	C7—C8	1.5180 (11)
O1—C12	1.4276 (11)	C7—H7A	0.98
O2—C13	1.2163 (10)	C8—C9	1.3565 (11)
O3—C13	1.3516 (10)	C8—C13	1.4698 (11)
O3—C14	1.4433 (11)	C9—C17	1.5040 (11)
O4—C15	1.2226 (10)	C10—C11	1.3603 (11)
O5—C15	1.3461 (10)	C10—C18	1.5026 (11)
O5—C16	1.4416 (11)	C11—C15	1.4637 (11)
N1—C10	1.3843 (10)	C12—H12A	0.96
N1—C9	1.3872 (11)	C12—H12B	0.96
N1—H1N1	0.871 (16)	C12—H12C	0.96
C1—C2	1.3885 (11)	C14—H14A	0.96
C1—C6	1.3938 (11)	C14—H14B	0.96
C1—H1A	0.93	C14—H14C	0.96
C2—C3	1.3925 (12)	C16—H16A	0.96
C2—H2A	0.93	C16—H16B	0.96
C3—C4	1.3912 (12)	C16—H16C	0.96
C4—C5	1.3928 (11)	C17—H17A	0.96
C4—H4A	0.93	C17—H17B	0.96
C5—C6	1.3901 (11)	C17—H17C	0.96
C5—H5A	0.93	C18—H18A	0.96
C6—C7	1.5252 (11)	C18—H18B	0.96
C7—C11	1.5172 (11)	C18—H18C	0.96

C3—O1—C12	116.97 (7)	C10—C11—C15	124.91 (8)
C13—O3—C14	115.18 (7)	C10—C11—C7	120.70 (7)
C15—O5—C16	116.31 (7)	C15—C11—C7	114.13 (7)
C10—N1—C9	124.03 (7)	O1—C12—H12A	109.5
C10—N1—H1N1	116.8 (10)	O1—C12—H12B	109.5
C9—N1—H1N1	118.7 (10)	H12A—C12—H12B	109.5
C2—C1—C6	121.53 (8)	O1—C12—H12C	109.5
C2—C1—H1A	119.2	H12A—C12—H12C	109.5
C6—C1—H1A	119.2	H12B—C12—H12C	109.5
C1—C2—C3	119.85 (8)	O2—C13—O3	121.96 (8)
C1—C2—H2A	120.1	O2—C13—C8	123.36 (8)
C3—C2—H2A	120.1	O3—C13—C8	114.65 (7)
O1—C3—C4	124.45 (8)	O3—C14—H14A	109.5
O1—C3—C2	115.92 (7)	O3—C14—H14B	109.5
C4—C3—C2	119.63 (8)	H14A—C14—H14B	109.5
C3—C4—C5	119.49 (8)	O3—C14—H14C	109.5
C3—C4—H4A	120.3	H14A—C14—H14C	109.5
C5—C4—H4A	120.3	H14B—C14—H14C	109.5
C6—C5—C4	121.82 (8)	O4—C15—O5	121.67 (8)
C6—C5—H5A	119.1	O4—C15—C11	123.13 (8)
C4—C5—H5A	119.1	O5—C15—C11	115.20 (7)
C5—C6—C1	117.64 (7)	O5—C16—H16A	109.5
C5—C6—C7	120.39 (7)	O5—C16—H16B	109.5
C1—C6—C7	121.96 (7)	H16A—C16—H16B	109.5
C11—C7—C8	111.44 (6)	O5—C16—H16C	109.5
C11—C7—C6	109.82 (6)	H16A—C16—H16C	109.5
C8—C7—C6	110.88 (6)	H16B—C16—H16C	109.5
C11—C7—H7A	108.2	C9—C17—H17A	109.5
C8—C7—H7A	108.2	C9—C17—H17B	109.5
C6—C7—H7A	108.2	H17A—C17—H17B	109.5
C9—C8—C13	125.21 (7)	C9—C17—H17C	109.5
C9—C8—C7	120.89 (7)	H17A—C17—H17C	109.5
C13—C8—C7	113.77 (7)	H17B—C17—H17C	109.5
C8—C9—N1	118.88 (7)	C10—C18—H18A	109.5
C8—C9—C17	127.61 (8)	C10—C18—H18B	109.5
N1—C9—C17	113.47 (7)	H18A—C18—H18B	109.5
C11—C10—N1	118.71 (7)	C10—C18—H18C	109.5
C11—C10—C18	127.85 (8)	H18A—C18—H18C	109.5
N1—C10—C18	113.43 (7)	H18B—C18—H18C	109.5

C6—C1—C2—C3	−0.14 (13)	C10—N1—C9—C8	12.37 (12)
C12—O1—C3—C4	−6.29 (13)	C10—N1—C9—C17	−165.74 (7)
C12—O1—C3—C2	173.39 (8)	C9—N1—C10—C11	−10.00 (12)
C1—C2—C3—O1	−178.08 (8)	C9—N1—C10—C18	169.89 (7)
C1—C2—C3—C4	1.62 (13)	N1—C10—C11—C15	176.50 (7)
O1—C3—C4—C5	178.06 (8)	C18—C10—C11—C15	−3.38 (14)
C2—C3—C4—C5	−1.60 (13)	N1—C10—C11—C7	−9.74 (12)
C3—C4—C5—C6	0.12 (14)	C18—C10—C11—C7	170.39 (8)
C4—C5—C6—C1	1.32 (13)	C8—C7—C11—C10	24.10 (10)
C4—C5—C6—C7	−177.87 (8)	C6—C7—C11—C10	−99.17 (9)
C2—C1—C6—C5	−1.31 (13)	C8—C7—C11—C15	−161.50 (7)
C2—C1—C6—C7	177.87 (8)	C6—C7—C11—C15	75.23 (8)
C5—C6—C7—C11	53.55 (10)	C14—O3—C13—O2	2.95 (12)
C1—C6—C7—C11	−125.60 (8)	C14—O3—C13—C8	−174.88 (7)
C5—C6—C7—C8	−70.05 (10)	C9—C8—C13—O2	173.87 (8)
C1—C6—C7—C8	110.80 (9)	C7—C8—C13—O2	−10.26 (12)
C11—C7—C8—C9	−21.76 (10)	C9—C8—C13—O3	−8.34 (12)
C6—C7—C8—C9	100.90 (9)	C7—C8—C13—O3	167.53 (7)
C11—C7—C8—C13	162.17 (7)	C16—O5—C15—O4	−4.05 (12)
C6—C7—C8—C13	−75.16 (8)	C16—O5—C15—C11	175.05 (7)
C13—C8—C9—N1	−179.23 (7)	C10—C11—C15—O4	−177.44 (8)
C7—C8—C9—N1	5.17 (12)	C7—C11—C15—O4	8.43 (11)
C13—C8—C9—C17	−1.42 (14)	C10—C11—C15—O5	3.48 (12)
C7—C8—C9—C17	−177.01 (8)	C7—C11—C15—O5	−170.65 (7)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4ⁱ	0.87 (2)	2.23 (2)	3.0906 (10)	169 (1)
C14—H14A···O1ⁱⁱ	0.96	2.54	3.4631 (13)	162
C18—H18B···O4ⁱ	0.96	2.56	3.4558 (12)	156
C12—H12B···Cg1ⁱⁱⁱ	0.96	2.79	3.6549 (11)	151

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁NO₅
M_r	331.36
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.4106 (3), 9.5715 (5), 11.7771 (6)
α, β, γ (°)	83.029 (1), 83.834 (1), 77.424 (1)
V (Å³)	806.46 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.34 × 0.24

Data collection
Diffractometer	Bruker SMART APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.966, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	19600, 4664, 4319
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.110, 1.05
No. of reflections	4664
No. of parameters	226
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.22

Computer programs: APEX DUO (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4ⁱ	0.87 (2)	2.23 (2)	3.0906 (10)	169 (1)
C14—H14A···O1ⁱⁱ	0.96	2.54	3.4631 (13)	162
C18—H18B···O4ⁱ	0.96	2.56	3.4558 (12)	156
C12—H12B···Cg1ⁱⁱⁱ	0.96	2.79	3.6549 (11)	151

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

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

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Volume 66| Part 3| March 2010| Pages o587-o588

doi:10.1107/S1600536810004940

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

Di­methyl 1,4-di­hydro-4-(4-meth­oxy­phen­yl)-2,6-di­methyl­pyridine-3,5-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Dimethyl 1,4-dihydro-4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate