Diethyl 4-(4-ethoxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

Fun, H.-K.; Goh, J.H.; Reddy, B.P.; Sarveswari, S.; Vijayakumar, V.

doi:10.1107/S160053680903339X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2247-o2248

doi:10.1107/S160053680903339X

Open

access

Diethyl 4-(4-ethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a B. Palakshi Reddy,^b S. Sarveswari ^b and V. Vijayakumar ^b

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

(Received 18 August 2009; accepted 21 August 2009; online 26 August 2009)

In the title compound, C₂₁H₂₇NO₅, the dihydropyridine ring adopts a boat conformation. The ethoxyphenyl ring is oriented approximately perpendicular to the planar part of the dihydropyridine ring, making a dihedral angle of 89.45 (6)°. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, neighbouring molecules are linked into chains along the a axis by N—H⋯O hydrogen bonds and the chains are interconnected into two-dimensional networks parallel to the ab plane by C—H⋯O hydrogen bonds. The structure is further stabilized by weak C—H⋯π interactions.

Related literature

For general background to and applications of 1,4-dihydropyridine derivatives, see: Böcker & Guengerich (1986 ); Cooper et al. (1992 ); Vo et al. (1995 ); Gaudio et al. (1994 ); Gordeev et al. (1996 ); Sunkel et al. (1992 ). For ring conformations and ring puckering analysis, see: Boeyens (1978 ); Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Thenmozhi et al. (2009 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₇NO₅
M_r = 373.44
Triclinic, $[P \overline 1]$
a = 7.5557 (1) Å
b = 9.5697 (1) Å
c = 14.0553 (2) Å
α = 85.844 (1)°
β = 87.679 (1)°
γ = 81.458 (1)°
V = 1001.91 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.28 × 0.27 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.976, T_max = 0.994
20664 measured reflections
5290 independent reflections
3602 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.161
S = 1.02
5290 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 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—H1N1⋯O2ⁱ	0.85 (2)	2.18 (2)	3.0045 (19)	165 (2)
C12—H12A⋯O4ⁱⁱ	0.97	2.51	3.458 (2)	166
C20—H20A⋯O3	0.96	2.14	2.7774 (19)	122
C16—H16A⋯Cg1ⁱⁱⁱ	0.96	2.83	3.767 (2)	165
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z; (iii) -x+2, -y+1, -z+2. Cg1 is the centroid of the C1–C6 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S160053680903339X/ci2893sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903339X/ci2893Isup2.hkl

checkCIF report

Comment top

Hantzsch 1,4-dihydropyridines (1,4-DHPS) are biologically active compounds which includes various vasodilator, anti-hypertensive, bronchodilator, heptaprotective, anti-tumor, anti-mutagenic, geroprotective and anti-diabetic agents (Gaudio et al., 1994). Nifedipine, nitrendipine and nimodipine have found commercial utility as calcium channel blockers (Böcker et al., 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 of DHPs have been introduced as a neuroprotectant and cognition enhancer. 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 dihydropyridine ring adopts a boat conformation (Boeyens, 1978; Cremer & Pople, 1975) with puckering amplitude Q = 0.2994 (16) Å, θ = 73.0 (3)° and ϕ = 181.7 (3)°. Atoms C7 and N1 deviate from the C8/C9/C10/C11 plane by 0.362 (2) and 0.143 (2) Å, respectively. The C1-C6 benzene ring is perpendicular to the C8-C11 plane, making a dihedral angle of 89.45 (6)°. An intramolecular C20—H20A···O3 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). Bond lengths (Allen et al., 1987) and angles are comparable to a related structure (Thenmozhi et al., 2009).

In the crystal structure (Fig. 2), neighbouring molecules are linked into chains along the a-axis by N1—H1N1···O2 hydrogen bonds (Table 1). These chains are interconnected into two-dimensional networks parallel to the ab plane by C12—H12A···O4 hydrogen bonds. The crystal structure is further stabilized by weak C16—H16A···Cg1 interactions (Table 1).

Related literature top

For general background to and applications of 1,4-dihydropyridine derivatives, see: Böcker & Guengerich (1986); Cooper et al. (1992); Vo et al. (1995); Gaudio et al. (1994); Gordeev et al. (1996); Sunkel et al. (1992). For ring conformations and ring puckering analysis, see: Boeyens (1978); Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For a related structure, see: Thenmozhi et al. (2009). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C1–C6 benzene ring.

Experimental top

The title compound was prepared according to Hantzsch pyridine synthesis. A mixture of 4-ethoxybenzaldehyde (10 mmol), ethylacetoacetate (20 mmol) and ammonium acetate (10 mmol) were heated at 353 K for 3 h (monitored by TLC). After completion of the reaction, the mixture was cooled to room temperature and kept for 2 days to get the solid product. The solid formed was washed using diethyl ether. After washing, the solid and the liquid was collected separately and the liquid was kept for solidification. The purity of the crude product was checked through TLC and recrystallized using acetone and ether (m.p. 377–379 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 25% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Two-dimensional network parallel to the ab plane, viewed along the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

Diethyl 4-(4-ethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₂₁H₂₇NO₅	Z = 2
M_r = 373.44	F(000) = 400
Triclinic, P1	D_x = 1.238 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5557 (1) Å	Cell parameters from 5893 reflections
b = 9.5697 (1) Å	θ = 2.5–30.2°
c = 14.0553 (2) Å	µ = 0.09 mm⁻¹
α = 85.844 (1)°	T = 296 K
β = 87.679 (1)°	Plate, colourless
γ = 81.458 (1)°	0.28 × 0.27 × 0.07 mm
V = 1001.91 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5290 independent reflections
Radiation source: fine-focus sealed tube	3602 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 29.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.976, T_max = 0.994	k = −11→13
20664 measured reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0714P)² + 0.3075P] where P = (F_o² + 2F_c²)/3
5290 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₇NO₅	γ = 81.458 (1)°
M_r = 373.44	V = 1001.91 (2) Å³
Triclinic, P1	Z = 2
a = 7.5557 (1) Å	Mo Kα radiation
b = 9.5697 (1) Å	µ = 0.09 mm⁻¹
c = 14.0553 (2) Å	T = 296 K
α = 85.844 (1)°	0.28 × 0.27 × 0.07 mm
β = 87.679 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5290 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3602 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.994	R_int = 0.027
20664 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.32 e Å⁻³
5290 reflections	Δρ_min = −0.24 e Å⁻³
253 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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 > 2sigma(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	0.73624 (18)	0.59395 (15)	0.53338 (9)	0.0547 (4)
O2	1.01269 (16)	0.23542 (17)	0.96209 (10)	0.0603 (4)
O3	0.81388 (15)	0.34092 (15)	1.06441 (9)	0.0511 (3)
O4	0.5806 (2)	−0.10910 (17)	0.71435 (11)	0.0672 (4)
O5	0.85133 (17)	−0.04519 (14)	0.72123 (9)	0.0525 (3)
N1	0.41011 (18)	0.18714 (16)	0.92272 (10)	0.0402 (3)
C1	0.8807 (2)	0.28106 (19)	0.68730 (11)	0.0416 (4)
H1A	0.9720	0.2043	0.6870	0.050*
C2	0.8726 (2)	0.3840 (2)	0.61279 (12)	0.0452 (4)
H2A	0.9583	0.3761	0.5633	0.054*
C3	0.7373 (2)	0.49899 (19)	0.61149 (11)	0.0412 (4)
C4	0.6152 (2)	0.5125 (2)	0.68730 (13)	0.0479 (4)
H4A	0.5267	0.5911	0.6886	0.058*
C5	0.6254 (2)	0.40778 (19)	0.76151 (12)	0.0431 (4)
H5A	0.5421	0.4175	0.8120	0.052*
C6	0.7553 (2)	0.28953 (17)	0.76285 (10)	0.0333 (3)
C7	0.7547 (2)	0.16927 (17)	0.84131 (10)	0.0328 (3)
H7A	0.8750	0.1144	0.8434	0.039*
C8	0.7073 (2)	0.22640 (17)	0.93892 (10)	0.0330 (3)
C9	0.5348 (2)	0.24150 (17)	0.97270 (10)	0.0347 (3)
C10	0.4537 (2)	0.09203 (17)	0.85327 (11)	0.0373 (4)
C11	0.6234 (2)	0.07125 (17)	0.81710 (10)	0.0352 (3)
C12	0.5781 (3)	0.6937 (2)	0.51790 (14)	0.0552 (5)
H12A	0.5585	0.7572	0.5692	0.066*
H12B	0.4748	0.6447	0.5159	0.066*
C13	0.6041 (4)	0.7752 (3)	0.42475 (17)	0.0825 (8)
H13A	0.4990	0.8427	0.4120	0.124*
H13B	0.6242	0.7112	0.3746	0.124*
H13C	0.7056	0.8241	0.4278	0.124*
C14	0.8579 (2)	0.26575 (18)	0.98833 (11)	0.0365 (4)
C15	0.9594 (2)	0.3755 (2)	1.11817 (13)	0.0532 (5)
H15A	1.0388	0.4248	1.0765	0.064*
H15B	1.0280	0.2897	1.1461	0.064*
C16	0.8798 (3)	0.4675 (3)	1.19452 (16)	0.0695 (6)
H16A	0.9730	0.4874	1.2336	0.104*
H16B	0.7964	0.4198	1.2331	0.104*
H16C	0.8185	0.5546	1.1660	0.104*
C17	0.6761 (2)	−0.03516 (18)	0.74743 (11)	0.0411 (4)
C18	0.9092 (3)	−0.1407 (3)	0.64637 (16)	0.0676 (6)
H18A	0.8361	−0.1144	0.5909	0.081*
H18B	0.8960	−0.2370	0.6687	0.081*
C19	1.0976 (4)	−0.1317 (4)	0.6207 (2)	0.1091 (12)
H19A	1.1366	−0.1932	0.5706	0.164*
H19B	1.1694	−0.1601	0.6755	0.164*
H19C	1.1098	−0.0360	0.5993	0.164*
C20	0.4542 (2)	0.3115 (2)	1.05970 (12)	0.0461 (4)
H20A	0.5452	0.3102	1.1056	0.069*
H20B	0.3613	0.2614	1.0870	0.069*
H20C	0.4046	0.4078	1.0421	0.069*
C21	0.2974 (2)	0.0239 (2)	0.82690 (14)	0.0506 (5)
H21A	0.3381	−0.0725	0.8130	0.076*
H21B	0.2427	0.0748	0.7717	0.076*
H21C	0.2114	0.0261	0.8792	0.076*
H1N1	0.303 (3)	0.200 (2)	0.9447 (15)	0.063 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0620 (8)	0.0562 (8)	0.0433 (7)	−0.0086 (7)	0.0050 (6)	0.0103 (6)
O2	0.0287 (6)	0.0946 (11)	0.0613 (8)	−0.0088 (6)	0.0039 (5)	−0.0333 (8)
O3	0.0326 (6)	0.0773 (9)	0.0471 (7)	−0.0096 (6)	−0.0008 (5)	−0.0263 (6)
O4	0.0660 (9)	0.0695 (10)	0.0748 (10)	−0.0262 (8)	0.0099 (7)	−0.0365 (8)
O5	0.0489 (7)	0.0514 (8)	0.0592 (8)	−0.0065 (6)	0.0092 (6)	−0.0238 (6)
N1	0.0265 (7)	0.0497 (9)	0.0451 (8)	−0.0061 (6)	0.0012 (5)	−0.0090 (6)
C1	0.0363 (8)	0.0457 (10)	0.0419 (8)	−0.0037 (7)	0.0077 (7)	−0.0057 (7)
C2	0.0461 (10)	0.0515 (11)	0.0379 (8)	−0.0093 (8)	0.0135 (7)	−0.0056 (7)
C3	0.0469 (9)	0.0434 (10)	0.0352 (8)	−0.0143 (8)	0.0019 (7)	−0.0016 (7)
C4	0.0484 (10)	0.0450 (10)	0.0464 (9)	0.0020 (8)	0.0080 (8)	0.0000 (8)
C5	0.0427 (9)	0.0446 (10)	0.0394 (8)	−0.0015 (7)	0.0118 (7)	−0.0024 (7)
C6	0.0320 (7)	0.0376 (8)	0.0321 (7)	−0.0090 (6)	0.0020 (6)	−0.0075 (6)
C7	0.0282 (7)	0.0370 (8)	0.0326 (7)	−0.0019 (6)	0.0023 (5)	−0.0058 (6)
C8	0.0289 (7)	0.0381 (8)	0.0318 (7)	−0.0037 (6)	0.0001 (5)	−0.0035 (6)
C9	0.0304 (7)	0.0394 (9)	0.0340 (7)	−0.0040 (6)	−0.0003 (6)	−0.0020 (6)
C10	0.0350 (8)	0.0365 (9)	0.0407 (8)	−0.0058 (7)	−0.0051 (6)	−0.0015 (7)
C11	0.0373 (8)	0.0347 (8)	0.0333 (7)	−0.0046 (6)	−0.0018 (6)	−0.0016 (6)
C12	0.0630 (12)	0.0531 (12)	0.0514 (10)	−0.0148 (10)	−0.0137 (9)	0.0034 (9)
C13	0.108 (2)	0.0797 (17)	0.0598 (13)	−0.0203 (15)	−0.0214 (13)	0.0220 (12)
C14	0.0313 (8)	0.0452 (9)	0.0334 (7)	−0.0064 (7)	0.0008 (6)	−0.0042 (6)
C15	0.0381 (9)	0.0764 (14)	0.0486 (10)	−0.0115 (9)	−0.0083 (7)	−0.0171 (9)
C16	0.0631 (13)	0.0843 (17)	0.0649 (13)	−0.0092 (12)	−0.0098 (10)	−0.0308 (12)
C17	0.0466 (9)	0.0382 (9)	0.0387 (8)	−0.0076 (7)	0.0001 (7)	−0.0028 (7)
C18	0.0696 (14)	0.0679 (15)	0.0687 (13)	−0.0092 (11)	0.0135 (11)	−0.0369 (11)
C19	0.0758 (18)	0.135 (3)	0.128 (3)	−0.0290 (18)	0.0381 (17)	−0.086 (2)
C20	0.0338 (8)	0.0614 (12)	0.0430 (9)	−0.0055 (8)	0.0073 (7)	−0.0116 (8)
C21	0.0377 (9)	0.0557 (12)	0.0617 (11)	−0.0132 (8)	−0.0060 (8)	−0.0110 (9)

Geometric parameters (Å, º) top

O1—C3	1.373 (2)	C10—C11	1.352 (2)
O1—C12	1.428 (2)	C10—C21	1.502 (2)
O2—C14	1.2115 (18)	C11—C17	1.465 (2)
O3—C14	1.3353 (19)	C12—C13	1.496 (3)
O3—C15	1.450 (2)	C12—H12A	0.97
O4—C17	1.210 (2)	C12—H12B	0.97
O5—C17	1.351 (2)	C13—H13A	0.96
O5—C18	1.455 (2)	C13—H13B	0.96
N1—C10	1.380 (2)	C13—H13C	0.96
N1—C9	1.380 (2)	C15—C16	1.488 (3)
N1—H1N1	0.85 (2)	C15—H15A	0.97
C1—C2	1.382 (2)	C15—H15B	0.97
C1—C6	1.393 (2)	C16—H16A	0.96
C1—H1A	0.93	C16—H16B	0.96
C2—C3	1.386 (3)	C16—H16C	0.96
C2—H2A	0.93	C18—C19	1.467 (3)
C3—C4	1.382 (2)	C18—H18A	0.97
C4—C5	1.389 (2)	C18—H18B	0.97
C4—H4A	0.93	C19—H19A	0.96
C5—C6	1.383 (2)	C19—H19B	0.96
C5—H5A	0.93	C19—H19C	0.96
C6—C7	1.535 (2)	C20—H20A	0.96
C7—C8	1.523 (2)	C20—H20B	0.96
C7—C11	1.527 (2)	C20—H20C	0.96
C7—H7A	0.98	C21—H21A	0.96
C8—C9	1.360 (2)	C21—H21B	0.96
C8—C14	1.466 (2)	C21—H21C	0.96
C9—C20	1.501 (2)

C3—O1—C12	117.87 (14)	C12—C13—H13A	109.5
C14—O3—C15	117.18 (13)	C12—C13—H13B	109.5
C17—O5—C18	115.21 (15)	H13A—C13—H13B	109.5
C10—N1—C9	123.89 (13)	C12—C13—H13C	109.5
C10—N1—H1N1	118.1 (15)	H13A—C13—H13C	109.5
C9—N1—H1N1	116.6 (15)	H13B—C13—H13C	109.5
C2—C1—C6	121.53 (16)	O2—C14—O3	121.24 (15)
C2—C1—H1A	119.2	O2—C14—C8	123.23 (14)
C6—C1—H1A	119.2	O3—C14—C8	115.52 (13)
C1—C2—C3	120.26 (15)	O3—C15—C16	107.77 (15)
C1—C2—H2A	119.9	O3—C15—H15A	110.2
C3—C2—H2A	119.9	C16—C15—H15A	110.2
O1—C3—C4	124.29 (16)	O3—C15—H15B	110.2
O1—C3—C2	116.40 (14)	C16—C15—H15B	110.2
C4—C3—C2	119.31 (15)	H15A—C15—H15B	108.5
C3—C4—C5	119.52 (16)	C15—C16—H16A	109.5
C3—C4—H4A	120.2	C15—C16—H16B	109.5
C5—C4—H4A	120.2	H16A—C16—H16B	109.5
C6—C5—C4	122.26 (15)	C15—C16—H16C	109.5
C6—C5—H5A	118.9	H16A—C16—H16C	109.5
C4—C5—H5A	118.9	H16B—C16—H16C	109.5
C5—C6—C1	117.05 (15)	O4—C17—O5	120.80 (16)
C5—C6—C7	121.32 (13)	O4—C17—C11	126.77 (16)
C1—C6—C7	121.55 (14)	O5—C17—C11	112.43 (14)
C8—C7—C11	110.43 (12)	O5—C18—C19	108.76 (19)
C8—C7—C6	111.55 (12)	O5—C18—H18A	109.9
C11—C7—C6	109.65 (12)	C19—C18—H18A	109.9
C8—C7—H7A	108.4	O5—C18—H18B	109.9
C11—C7—H7A	108.4	C19—C18—H18B	109.9
C6—C7—H7A	108.4	H18A—C18—H18B	108.3
C9—C8—C14	124.96 (14)	C18—C19—H19A	109.5
C9—C8—C7	120.06 (13)	C18—C19—H19B	109.5
C14—C8—C7	114.94 (12)	H19A—C19—H19B	109.5
C8—C9—N1	118.44 (14)	C18—C19—H19C	109.5
C8—C9—C20	129.12 (15)	H19A—C19—H19C	109.5
N1—C9—C20	112.44 (13)	H19B—C19—H19C	109.5
C11—C10—N1	119.10 (15)	C9—C20—H20A	109.5
C11—C10—C21	128.03 (15)	C9—C20—H20B	109.5
N1—C10—C21	112.87 (14)	H20A—C20—H20B	109.5
C10—C11—C17	120.26 (15)	C9—C20—H20C	109.5
C10—C11—C7	119.61 (14)	H20A—C20—H20C	109.5
C17—C11—C7	119.84 (13)	H20B—C20—H20C	109.5
O1—C12—C13	107.53 (18)	C10—C21—H21A	109.5
O1—C12—H12A	110.2	C10—C21—H21B	109.5
C13—C12—H12A	110.2	H21A—C21—H21B	109.5
O1—C12—H12B	110.2	C10—C21—H21C	109.5
C13—C12—H12B	110.2	H21A—C21—H21C	109.5
H12A—C12—H12B	108.5	H21B—C21—H21C	109.5

C6—C1—C2—C3	−0.3 (3)	C9—N1—C10—C11	−14.2 (2)
C12—O1—C3—C4	−15.4 (3)	C9—N1—C10—C21	166.34 (16)
C12—O1—C3—C2	165.31 (16)	N1—C10—C11—C17	176.38 (14)
C1—C2—C3—O1	−178.08 (16)	C21—C10—C11—C17	−4.2 (3)
C1—C2—C3—C4	2.6 (3)	N1—C10—C11—C7	−9.8 (2)
O1—C3—C4—C5	178.09 (17)	C21—C10—C11—C7	169.58 (16)
C2—C3—C4—C5	−2.7 (3)	C8—C7—C11—C10	29.0 (2)
C3—C4—C5—C6	0.4 (3)	C6—C7—C11—C10	−94.32 (16)
C4—C5—C6—C1	1.9 (3)	C8—C7—C11—C17	−157.19 (13)
C4—C5—C6—C7	−174.85 (16)	C6—C7—C11—C17	79.49 (17)
C2—C1—C6—C5	−1.9 (3)	C3—O1—C12—C13	−174.91 (18)
C2—C1—C6—C7	174.78 (16)	C15—O3—C14—O2	−4.4 (3)
C5—C6—C7—C8	−40.9 (2)	C15—O3—C14—C8	176.84 (15)
C1—C6—C7—C8	142.47 (15)	C9—C8—C14—O2	170.76 (18)
C5—C6—C7—C11	81.70 (18)	C7—C8—C14—O2	−11.3 (2)
C1—C6—C7—C11	−94.88 (17)	C9—C8—C14—O3	−10.5 (2)
C11—C7—C8—C9	−28.3 (2)	C7—C8—C14—O3	167.43 (14)
C6—C7—C8—C9	93.93 (17)	C14—O3—C15—C16	175.95 (18)
C11—C7—C8—C14	153.64 (13)	C18—O5—C17—O4	4.9 (3)
C6—C7—C8—C14	−84.16 (16)	C18—O5—C17—C11	−175.20 (16)
C14—C8—C9—N1	−173.78 (15)	C10—C11—C17—O4	2.0 (3)
C7—C8—C9—N1	8.3 (2)	C7—C11—C17—O4	−171.78 (17)
C14—C8—C9—C20	6.4 (3)	C10—C11—C17—O5	−177.96 (15)
C7—C8—C9—C20	−171.48 (16)	C7—C11—C17—O5	8.3 (2)
C10—N1—C9—C8	14.9 (2)	C17—O5—C18—C19	175.6 (2)
C10—N1—C9—C20	−165.23 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.85 (2)	2.18 (2)	3.0045 (19)	165 (2)
C12—H12A···O4ⁱⁱ	0.97	2.51	3.458 (2)	166
C20—H20A···O3	0.96	2.14	2.7774 (19)	122
C16—H16A···Cg1ⁱⁱⁱ	0.96	2.83	3.767 (2)	165

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₇NO₅
M_r	373.44
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5557 (1), 9.5697 (1), 14.0553 (2)
α, β, γ (°)	85.844 (1), 87.679 (1), 81.458 (1)
V (Å³)	1001.91 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.27 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.976, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	20664, 5290, 3602
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.161, 1.02
No. of reflections	5290
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.85 (2)	2.18 (2)	3.0045 (19)	165 (2)
C12—H12A···O4ⁱⁱ	0.97	2.51	3.458 (2)	166
C20—H20A···O3	0.96	2.14	2.7774 (19)	122
C16—H16A···Cg1ⁱⁱⁱ	0.96	2.83	3.767 (2)	165

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. VV is grateful to DST–India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Böcker, R. H. & Guengerich, F. P. (1986). J. Med. Chem. 29, 1596–1603. PubMed Web of Science Google Scholar
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cooper, K., Fray, M. J., Parry, M. J., Richardson, K. & Steele, J. (1992). J. Med. Chem. 35, 3115–3129. CrossRef PubMed CAS Web of Science Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Gaudio, A. C., Korolkovas, A. & Takahata, Y. (1994). J. Pharm. Sci. 84, 1110–1115. CrossRef Web of Science Google Scholar
Gordeev, M. F., Patel, D. V. & Gordon, E. M. (1996). J. Org. Chem. 61, 924–928. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sunkel, C. E., de Casa-Juana, M. F., Santos, L., Garcia, A. G., Artalejo, C. R., Villarroya, M., González-Morales, M. A., López, M. G., Cillero, J., Alonso, S. & Priego, J. G. (1992). J. Med. Chem. 35, 2407–2414. CrossRef PubMed CAS Web of Science Google Scholar
Thenmozhi, M., Kavitha, T., Satyanarayana, V. S. V., Vijayakumar, V. & Ponnuswamy, M. N. (2009). Acta Cryst. E65, o1921–o1922. Web of Science CSD CrossRef IUCr Journals Google Scholar
Vo, D., Matowe, W. C., Ramesh, M., Iqbal, N., Wolowyk, M. W., Howlett, S. E. & Knaus, E. E. (1995). J. Med. Chem. 38, 2851–2859. CrossRef CAS PubMed Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2247-o2248

doi:10.1107/S160053680903339X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Di­ethyl 4-(4-eth­oxy­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Diethyl 4-(4-ethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate