3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-1,4-dihydro­pyridine-4-carboxylic acid

Wu, D.-H.; Hu, L.

doi:10.1107/S1600536809024945

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1748

doi:10.1107/S1600536809024945

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3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid

De-Hong Wu ^a ^* and Ling Hu ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, School of Materials Science and Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: wudehong@seu.edu.cn

(Received 13 May 2009; accepted 29 June 2009; online 4 July 2009)

The title molecule, C₁₄H₁₉NO₆, was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH₄HCO₃. In the crystal structure, the dihydropyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviation [0.325 (2) Å] from the base plane then the N atom [0.137 (2) Å]. One of the ethyl groups is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong intermolecular hydrogen bonds. N—H⋯O interactions form infinite chains in the a direction. O—H⋯O hydrogen bonds form typical carboxylic acid dimers, which link the N—H⋯O chains into a ladder-type double chain.

Related literature

For the electrophysiological activity of 1,4-dipyridine derivatives, see: Fleckenstein (1977 ); Cutshall et al. (2002 ). For their biological activity, see: Triggle et al. (1980 ); Fossheim et al. (1982 ); Heinrich et al. (2004 ); Henry (2004 ).

Experimental

Crystal data

C₁₄H₁₉NO₆
M_r = 297.30
Triclinic, $[P \overline 1]$
a = 7.445 (4) Å
b = 9.864 (5) Å
c = 11.908 (2) Å
α = 104.10 (3)°
β = 97.808 (9)°
γ = 111.658 (10)°
V = 763.2 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 K
0.36 × 0.30 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.960, T_max = 0.970
6950 measured reflections
2969 independent reflections
2241 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.197
S = 1.08
2969 reflections
199 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O5ⁱ	0.86	2.17	3.018 (2)	167
O2—H2A⋯O1ⁱⁱ	0.82	1.82	2.641 (2)	176
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z.

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809024945/kj2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024945/kj2129Isup2.hkl

checkCIF report

Comment top

The development of new methods for the synthesis of 1,4-dipyridine derivatives is a motive for the current research because of their presence in numerous natural products along with a wide spectrum of their electrophysiological activities (Fleckenstein, 1977; Cutshall et al., 2002). Pyridine 1,4-derivatives and their complexes have been studied for their fungicidal and antibacterial effects, antiviral drugs, as well as calcium antagonists (Triggle et al., 1980; Fossheim et al., 1982; Heinrich et al., 2004; Henry, 2004).

Here we report the structure of 3,5-di(ethoxycarbonyl)-1,4-dihydro-2,6-dimethylpyridine-4- carboxylic acid (Fig. 1). In the crystal structure, the dihydropyridine ring adopts a asymmetric boat-type conformation with C1 showing a signficantly larger deviation from the base plane C3/C4/C5/C6 [0.325 (2) Å] then N1 [0.137 (2) Å]. The ethyl group labeled by C9 and C10 is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong intermolecular hydrogen bonds (Table 1). Interactions of type N—H···O form infinite chains in the a-direction. The O—H···O hydrogen bonds form typical carboxylic acid dimers which link the N—H···O chains into a ladder-type double chain (Fig. 2).

Related literature top

For general background to 1,4-dipyridine derivatives, see: Fleckenstein (1977);Triggle et al. (1980); Fossheim et al. (1982); Cutshall et al. (2002); Heinrich et al. (2004); Henry (2004).

Experimental top

Glyoxylic acid (50% in water, 6 mmol), ethyl acetoacetate (12 mmol) and NH₄HCO₃ (6 mmol) were mixed in a 50 ml flask. After the mixture had been stirred for 6 h at 293 K, the crude product was obtained with yield of 65%. Single crystals suitable for X-ray structure analysis were obtained by the slow evaporation of a dimethylformamide solution in air.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. The molecular structure of the title compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids. All disorder components are shown.
	Fig. 2. The crystal packing of the title compound, viewed down the b axis, showing chains along the [100] direction. Hydrogen bonds are shown as dashed lines. The hydrogen atoms except for H1D and H2D are omitted. Only major disorder components are shown.

3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid top

Crystal data top

C₁₄H₁₉NO₆	Z = 2
M_r = 297.30	F(000) = 316
Triclinic, P1	D_x = 1.294 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.445 (4) Å	Cell parameters from 2034 reflections
b = 9.864 (5) Å	θ = 2.3–27.5°
c = 11.908 (2) Å	µ = 0.10 mm⁻¹
α = 104.10 (3)°	T = 291 K
β = 97.808 (9)°	Block, colourless
γ = 111.658 (10)°	0.36 × 0.30 × 0.28 mm
V = 763.2 (6) Å³

Data collection top

Rigaku SCXmini diffractometer	2969 independent reflections
Radiation source: fine-focus sealed tube	2241 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.960, T_max = 0.970	l = −14→14
6950 measured reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.115P)² + 0.1066P] where P = (F_o² + 2F_c²)/3
2969 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.29 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₉NO₆	γ = 111.658 (10)°
M_r = 297.30	V = 763.2 (6) Å³
Triclinic, P1	Z = 2
a = 7.445 (4) Å	Mo Kα radiation
b = 9.864 (5) Å	µ = 0.10 mm⁻¹
c = 11.908 (2) Å	T = 291 K
α = 104.10 (3)°	0.36 × 0.30 × 0.28 mm
β = 97.808 (9)°

Data collection top

Rigaku SCXmini diffractometer	2969 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2241 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.970	R_int = 0.029
6950 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	2 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 1.08	Δρ_max = 0.29 e Å⁻³
2969 reflections	Δρ_min = −0.24 e Å⁻³
199 parameters

Special details top

Experimental. 1H NMR (DMSO-d6, p.p.m.): δ 1.17 (t, J = 7.0 Hz, 6H, CH2CH3), 2.21 (s, 6H, Me), 4.07 (m, J = 7.0 Hz, 4H, CH2CH3), 4.58 (s, 1H, CH), 8.84 (s, 1H, NH), 11.89 (S, 1H, OH). 13 C NMR (DMSO-d6, p.p.m.): δ 14.72 (CH2CH3), 18.39 (CH3), 39.71 (CH in dihydropyridine ring), 59.55 (CH2), 97.68, 146.27 (quaternary C in dihydropyridine ring), 167.33 (CO), 175.02 (COOH).

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	Occ. (<1)
C1	0.5752 (3)	0.3833 (2)	0.24556 (18)	0.0403 (5)
H1A	0.4891	0.4029	0.2968	0.048*
C2	0.5338 (3)	0.4308 (2)	0.13568 (18)	0.0418 (5)
C3	0.7927 (3)	0.4825 (2)	0.31506 (19)	0.0471 (5)
C4	0.9329 (3)	0.4276 (3)	0.29898 (19)	0.0482 (5)
C5	0.6783 (3)	0.1670 (2)	0.19748 (19)	0.0447 (5)
C6	0.5295 (3)	0.2141 (2)	0.21075 (17)	0.0403 (5)
C7	1.1547 (3)	0.5129 (3)	0.3518 (3)	0.0700 (7)
H7A	1.1858	0.6168	0.3980	0.105*
H7B	1.2223	0.5136	0.2887	0.105*
H7C	1.1974	0.4627	0.4026	0.105*
C8	0.8460 (4)	0.6388 (3)	0.3946 (2)	0.0691 (7)
C9	0.7022 (9)	0.7955 (6)	0.5064 (4)	0.0796 (16)	0.742 (10)
H9A	0.8340	0.8514	0.5609	0.096*	0.742 (10)
H9B	0.6041	0.7752	0.5532	0.096*	0.742 (10)
C10	0.6670 (9)	0.8858 (5)	0.4323 (6)	0.109 (2)	0.742 (10)
H10D	0.6721	0.9802	0.4824	0.164*	0.742 (10)
H10E	0.5379	0.8281	0.3771	0.164*	0.742 (10)
H10F	0.7678	0.9085	0.3887	0.164*	0.742 (10)
C11	0.6588 (4)	0.0046 (3)	0.1497 (3)	0.0639 (7)
H11A	0.5206	−0.0659	0.1283	0.096*
H11B	0.7320	−0.0178	0.2100	0.096*
H11C	0.7114	−0.0059	0.0804	0.096*
C12	0.3169 (3)	0.1123 (2)	0.18269 (19)	0.0439 (5)
C13	0.0631 (4)	−0.1451 (3)	0.1230 (3)	0.0734 (8)
H13A	−0.0118	−0.1280	0.0588	0.088*
H13B	0.0062	−0.1315	0.1913	0.088*
C14	0.0555 (5)	−0.3023 (3)	0.0839 (4)	0.0916 (11)
H14A	−0.0808	−0.3768	0.0618	0.137*
H14B	0.1301	−0.3177	0.1482	0.137*
H14C	0.1121	−0.3142	0.0164	0.137*
C9'	0.7854 (18)	0.8432 (14)	0.4818 (12)	0.065 (4)*	0.258 (10)
H9'A	0.8895	0.8831	0.5551	0.078*	0.258 (10)
H9'B	0.8364	0.8910	0.4238	0.078*	0.258 (10)
C10'	0.5997 (16)	0.8597 (14)	0.5033 (11)	0.070 (4)*	0.258 (10)
H10A	0.6312	0.9662	0.5417	0.105*	0.258 (10)
H10B	0.5459	0.8009	0.5538	0.105*	0.258 (10)
H10C	0.5030	0.8227	0.4283	0.105*	0.258 (10)
N1	0.8729 (2)	0.2761 (2)	0.23053 (18)	0.0502 (5)
H1D	0.9620	0.2484	0.2073	0.060*
O1	0.5162 (3)	0.35326 (19)	0.03480 (14)	0.0690 (5)
O2	0.5283 (3)	0.56518 (19)	0.15897 (15)	0.0760 (6)
H2A	0.5144	0.5865	0.0969	0.114*
O3	1.0104 (4)	0.7427 (3)	0.4291 (3)	0.1314 (12)
O4	0.6867 (3)	0.6538 (2)	0.42828 (16)	0.0787 (6)
O5	0.1878 (2)	0.16074 (18)	0.18443 (16)	0.0603 (5)
O6	0.2733 (2)	−0.03741 (17)	0.15535 (18)	0.0639 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0385 (10)	0.0393 (10)	0.0487 (11)	0.0212 (8)	0.0147 (8)	0.0137 (8)
C2	0.0404 (10)	0.0340 (10)	0.0518 (12)	0.0200 (8)	0.0104 (8)	0.0091 (9)
C3	0.0447 (11)	0.0448 (11)	0.0502 (12)	0.0201 (9)	0.0089 (9)	0.0117 (9)
C4	0.0402 (11)	0.0529 (12)	0.0527 (12)	0.0210 (9)	0.0110 (9)	0.0169 (10)
C5	0.0443 (11)	0.0453 (11)	0.0554 (12)	0.0265 (9)	0.0186 (9)	0.0191 (9)
C6	0.0391 (10)	0.0404 (10)	0.0485 (11)	0.0221 (9)	0.0143 (8)	0.0159 (9)
C7	0.0421 (12)	0.0737 (17)	0.0839 (18)	0.0226 (12)	0.0055 (11)	0.0162 (14)
C8	0.0668 (16)	0.0540 (14)	0.0696 (16)	0.0268 (13)	−0.0015 (12)	−0.0009 (12)
C9	0.102 (4)	0.070 (3)	0.062 (2)	0.047 (3)	0.017 (2)	−0.004 (2)
C10	0.120 (4)	0.052 (2)	0.130 (5)	0.029 (3)	0.012 (4)	0.007 (3)
C11	0.0567 (14)	0.0494 (13)	0.0981 (19)	0.0345 (12)	0.0273 (13)	0.0212 (13)
C12	0.0423 (11)	0.0406 (11)	0.0555 (12)	0.0228 (9)	0.0169 (9)	0.0160 (9)
C13	0.0475 (13)	0.0486 (14)	0.124 (2)	0.0173 (11)	0.0306 (14)	0.0259 (15)
C14	0.0775 (19)	0.0460 (14)	0.148 (3)	0.0191 (14)	0.043 (2)	0.0279 (17)
N1	0.0374 (9)	0.0496 (10)	0.0691 (12)	0.0240 (8)	0.0191 (8)	0.0161 (9)
O1	0.1177 (15)	0.0498 (9)	0.0501 (10)	0.0486 (10)	0.0179 (9)	0.0143 (8)
O2	0.1359 (18)	0.0542 (10)	0.0573 (10)	0.0630 (12)	0.0200 (10)	0.0166 (8)
O3	0.0760 (15)	0.0632 (14)	0.184 (3)	0.0120 (12)	−0.0075 (16)	−0.0318 (16)
O4	0.0949 (14)	0.0754 (13)	0.0623 (11)	0.0545 (11)	0.0071 (10)	−0.0064 (9)
O5	0.0400 (8)	0.0500 (9)	0.0941 (13)	0.0261 (7)	0.0178 (8)	0.0163 (8)
O6	0.0432 (8)	0.0396 (8)	0.1140 (14)	0.0194 (7)	0.0259 (9)	0.0266 (9)

Geometric parameters (Å, º) top

C1—C6	1.510 (3)	C10—H10E	0.9600
C1—C2	1.524 (3)	C10—H10F	0.9600
C1—C3	1.528 (3)	C11—H11A	0.9600
C1—H1A	0.9800	C11—H11B	0.9600
C2—O1	1.217 (3)	C11—H11C	0.9600
C2—O2	1.304 (2)	C12—O5	1.222 (2)
C3—C4	1.357 (3)	C12—O6	1.332 (2)
C3—C8	1.472 (3)	C13—O6	1.462 (3)
C4—N1	1.383 (3)	C13—C14	1.483 (4)
C4—C7	1.505 (3)	C13—H13A	0.9700
C5—C6	1.363 (3)	C13—H13B	0.9700
C5—N1	1.378 (3)	C14—H14A	0.9600
C5—C11	1.508 (3)	C14—H14B	0.9600
C6—C12	1.465 (3)	C14—H14C	0.9600
C7—H7A	0.9600	C9'—C10'	1.499 (15)
C7—H7B	0.9600	C9'—O4	1.649 (12)
C7—H7C	0.9600	C9'—H9'A	0.9700
C8—O3	1.204 (3)	C9'—H9'B	0.9700
C8—O4	1.348 (3)	C10'—H10A	0.9600
C9—O4	1.432 (4)	C10'—H10B	0.9600
C9—C10	1.461 (8)	C10'—H10C	0.9600
C9—H9A	0.9700	N1—H1D	0.8600
C9—H9B	0.9700	O2—H2A	0.8200
C10—H10D	0.9600

C6—C1—C2	111.10 (16)	H10E—C10—H10F	109.5
C6—C1—C3	111.42 (16)	C5—C11—H11A	109.5
C2—C1—C3	108.83 (16)	C5—C11—H11B	109.5
C6—C1—H1A	108.5	H11A—C11—H11B	109.5
C2—C1—H1A	108.5	C5—C11—H11C	109.5
C3—C1—H1A	108.5	H11A—C11—H11C	109.5
O1—C2—O2	122.4 (2)	H11B—C11—H11C	109.5
O1—C2—C1	122.99 (17)	O5—C12—O6	122.05 (19)
O2—C2—C1	114.51 (17)	O5—C12—C6	122.53 (19)
C4—C3—C8	121.5 (2)	O6—C12—C6	115.42 (17)
C4—C3—C1	119.72 (19)	O6—C13—C14	106.9 (2)
C8—C3—C1	118.72 (19)	O6—C13—H13A	110.3
C3—C4—N1	119.07 (18)	C14—C13—H13A	110.3
C3—C4—C7	127.0 (2)	O6—C13—H13B	110.3
N1—C4—C7	113.86 (19)	C14—C13—H13B	110.3
C6—C5—N1	118.93 (18)	H13A—C13—H13B	108.6
C6—C5—C11	127.8 (2)	C13—C14—H14A	109.5
N1—C5—C11	113.28 (17)	C13—C14—H14B	109.5
C5—C6—C12	125.35 (19)	H14A—C14—H14B	109.5
C5—C6—C1	120.07 (18)	C13—C14—H14C	109.5
C12—C6—C1	114.31 (16)	H14A—C14—H14C	109.5
C4—C7—H7A	109.5	H14B—C14—H14C	109.5
C4—C7—H7B	109.5	C10'—C9'—O4	97.3 (9)
H7A—C7—H7B	109.5	C10'—C9'—H9'A	112.3
C4—C7—H7C	109.5	O4—C9'—H9'A	112.3
H7A—C7—H7C	109.5	C10'—C9'—H9'B	112.3
H7B—C7—H7C	109.5	O4—C9'—H9'B	112.3
O3—C8—O4	122.4 (3)	H9'A—C9'—H9'B	109.9
O3—C8—C3	125.8 (3)	C9'—C10'—H10A	109.5
O4—C8—C3	111.8 (2)	C9'—C10'—H10B	109.5
O4—C9—C10	107.7 (4)	H10A—C10'—H10B	109.5
O4—C9—H9A	110.2	C9'—C10'—H10C	109.5
C10—C9—H9A	110.2	H10A—C10'—H10C	109.5
O4—C9—H9B	110.2	H10B—C10'—H10C	109.5
C10—C9—H9B	110.2	C5—N1—C4	123.75 (16)
H9A—C9—H9B	108.5	C5—N1—H1D	118.1
C9—C10—H10D	109.5	C4—N1—H1D	118.1
C9—C10—H10E	109.5	C2—O2—H2A	109.5
H10D—C10—H10E	109.5	C8—O4—C9	121.9 (3)
C9—C10—H10F	109.5	C8—O4—C9'	97.6 (5)
H10D—C10—H10F	109.5	C12—O6—C13	117.96 (17)

C6—C1—C2—O1	−17.2 (3)	C1—C3—C8—O3	−158.8 (3)
C3—C1—C2—O1	105.9 (2)	C4—C3—C8—O4	−160.1 (2)
C6—C1—C2—O2	166.01 (18)	C1—C3—C8—O4	22.5 (3)
C3—C1—C2—O2	−70.9 (2)	C5—C6—C12—O5	−172.2 (2)
C6—C1—C3—C4	25.8 (3)	C1—C6—C12—O5	1.8 (3)
C2—C1—C3—C4	−97.1 (2)	C5—C6—C12—O6	8.0 (3)
C6—C1—C3—C8	−156.7 (2)	C1—C6—C12—O6	−177.98 (17)
C2—C1—C3—C8	80.4 (2)	C6—C5—N1—C4	13.9 (3)
C8—C3—C4—N1	175.1 (2)	C11—C5—N1—C4	−166.0 (2)
C1—C3—C4—N1	−7.5 (3)	C3—C4—N1—C5	−14.1 (3)
C8—C3—C4—C7	−2.6 (4)	C7—C4—N1—C5	163.9 (2)
C1—C3—C4—C7	174.8 (2)	O3—C8—O4—C9	0.8 (5)
N1—C5—C6—C12	−178.35 (18)	C3—C8—O4—C9	179.6 (3)
C11—C5—C6—C12	1.5 (4)	O3—C8—O4—C9'	15.3 (6)
N1—C5—C6—C1	8.0 (3)	C3—C8—O4—C9'	−165.9 (5)
C11—C5—C6—C1	−172.2 (2)	C10—C9—O4—C8	89.7 (5)
C2—C1—C6—C5	95.5 (2)	C10'—C9'—O4—C8	172.6 (8)
C3—C1—C6—C5	−26.0 (3)	O5—C12—O6—C13	2.0 (3)
C2—C1—C6—C12	−78.8 (2)	C6—C12—O6—C13	−178.2 (2)
C3—C1—C6—C12	159.62 (17)	C14—C13—O6—C12	173.7 (2)
C4—C3—C8—O3	18.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O5ⁱ	0.86	2.17	3.018 (2)	167
O2—H2A···O1ⁱⁱ	0.82	1.82	2.641 (2)	176

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉NO₆
M_r	297.30
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.445 (4), 9.864 (5), 11.908 (2)
α, β, γ (°)	104.10 (3), 97.808 (9), 111.658 (10)
V (Å³)	763.2 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.30 × 0.28

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.960, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	6950, 2969, 2241
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.197, 1.08
No. of reflections	2969
No. of parameters	199
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: CrystalClear (Rigaku, 2005), 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
N1—H1D···O5ⁱ	0.86	2.17	3.018 (2)	166.8
O2—H2A···O1ⁱⁱ	0.82	1.82	2.641 (2)	175.9

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

Acknowledgements

The authors thank Jiangsu Planned Projects for Postdoctoral Research Funds (grant No. 0802003B) and Professor Dr Rengen Xiong.

References

Cutshall, N. S., Kucera, K. A., Ursion, R., Latham, J. & Ihle, N. C. (2002). Bioorg. Med. Chem. Lett. 12, 1517–1520. Web of Science CrossRef PubMed CAS Google Scholar
Fleckenstein, A. (1977). Annu. Rev. Pharmacol. Toxicol. 17, 149–166. CrossRef CAS PubMed Web of Science Google Scholar
Fossheim, R., Svarteng, K., Mostad, A., Roemming, C., Shefter, E. & Triggle, D. J. (1982). J. Med. Chem. 25, 126–131. CSD CrossRef CAS PubMed Web of Science Google Scholar
Heinrich, T., Burschka, C., Warneck, J. & Tacke, R. (2004). Organometallics, 23, 361–366. Web of Science CSD CrossRef CAS Google Scholar
Henry, G. D. (2004). Tetrahedron, 60, 6043–6061. Web of Science CrossRef CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Triggle, A. M., Shefter, E. & Triggle, D. J. (1980). J. Med. Chem. 23, 1442–1445. CrossRef CAS PubMed Web of Science Google Scholar

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Volume 65| Part 8| August 2009| Page o1748

doi:10.1107/S1600536809024945

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

3,5-Bis(eth­oxy­carbon­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-4-carboxylic acid

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid