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

Zhao, Y.; Hibbs, D.E.; Groundwater, P.W.; Wassef, A.

doi:10.1107/S160053681202750X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2536

https://doi.org/10.1107/S160053681202750X

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

Yiliang Zhao,^a ^* David E. Hibbs,^a Paul W. Groundwater ^a and Abram Wassef ^a

^aFaculty of Pharmacy, The University of Sydney, NSW 2006, Australia
^*Correspondence e-mail: yiliang.zhao@sydney.edu.au

(Received 31 May 2012; accepted 18 June 2012; online 25 July 2012)

The title compound, C₂₁H₂₆N₂O₅, was unexpectedly obtained as a by-product in the reaction of ethyl acetoacetate, 4-acetamidobenzaldehyde and urea under microwave irradiation. The dihydropyridine ring assumes a flattened boat conformation. Intermolecular N—H⋯O and weak C—H⋯O hydrogen bonding occurs in the crystal.

Related literature

For the Biginelli dihydropyrimidone and Hantzsch dihydropyridine syntheses, see: Kappe & Stadler (2004 ); Kumar & Maurya (2008 ). For the microwave synthesis and melting point of 4-(3-acetamidophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, see: Mobinikhaledi & Foroughifar (2006 ).

Experimental

Crystal data

C₂₁H₂₆N₂O₅
M_r = 386.44
Monoclinic, P 2₁ /n
a = 11.3359 (7) Å
b = 12.1934 (7) Å
c = 15.3262 (9) Å
β = 109.745 (1)°
V = 1993.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.2 × 0.2 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.976, T_max = 0.988
15313 measured reflections
4593 independent reflections
3602 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.05
4593 reflections
266 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.892 (19)	2.022 (19)	2.8946 (17)	165.5 (16)
N2—H2⋯O3ⁱⁱ	0.866 (19)	2.074 (19)	2.9383 (17)	175.4 (16)
C6—H6A⋯O1ⁱⁱⁱ	0.98	2.52	3.370 (2)	145
C13—H13A⋯O1^iv	0.98	2.38	3.337 (2)	165
Symmetry codes: (i) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681202750X/xu5556sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202750X/xu5556Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681202750X/xu5556Isup3.cml

checkCIF report

Comment top

The bond lengths and angles in the title compound are as expected. The maximum deviation from the mean plane of the central ring is 0.188 (1) A for C1. The C8 and C11 carboxylate side chains are essentially planar, with a maximum deviation of 0.077 A for C10. These groups are set at 11.64 (8)° and 25.65 (4)° to the central ring plane respectively.

Related literature top

For the Biginelli dihydropyrimidone and Hantzsch dihydropyridine syntheses, see: Kappe & Stadler (2004); Kumar & Maurya (2008). For the microwave synthesis and melting point of 4-(3-acetamidophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, see: Mobinikhaledi & Foroughifar (2006).

Experimental top

A mixture of 4-acetamidobenzaldehyde (163 mg, 1 mmol), ethyl acetoacetate (130 mg, 1 mmol) and urea (60 mg, 1 mmol) was stirred for 2 h at 403 K under microwave irradiation. After completion of the reaction, TLC showed the presence of two main products, which were separated using silica chromatography, eluting with dichloromthane/methanol to give diethyl 4-acetamidophenyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (120 mg, 31%, mp 254–256°C), and ethyl 4-(3-acetamidophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (72 mg, 23%, mp 284–286°C).

Structure description top

For the Biginelli dihydropyrimidone and Hantzsch dihydropyridine syntheses, see: Kappe & Stadler (2004); Kumar & Maurya (2008). For the microwave synthesis and melting point of 4-(3-acetamidophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, see: Mobinikhaledi & Foroughifar (2006).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids for non-H atoms.

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

Crystal data top

C₂₁H₂₆N₂O₅	D_x = 1.287 Mg m⁻³
M_r = 386.44	Melting point: 256 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.3359 (7) Å	Cell parameters from 15313 reflections
b = 12.1934 (7) Å	θ = 2.0–28.3°
c = 15.3262 (9) Å	µ = 0.09 mm⁻¹
β = 109.745 (1)°	T = 150 K
V = 1993.9 (2) Å³	Block, clear colourless
Z = 4	0.2 × 0.2 × 0.15 mm
F(000) = 824

Data collection top

Bruker APEXII CCD area-detector diffractometer	4593 independent reflections
Radiation source: sealed tube	3602 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 8 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ω and φ scans	h = −15→14
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −15→14
T_min = 0.976, T_max = 0.988	l = −18→19
15313 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0575P)² + 0.5603P] where P = (F_o² + 2F_c²)/3
4593 reflections	(Δ/σ)_max < 0.001
266 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₂₆N₂O₅	V = 1993.9 (2) Å³
M_r = 386.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.3359 (7) Å	µ = 0.09 mm⁻¹
b = 12.1934 (7) Å	T = 150 K
c = 15.3262 (9) Å	0.2 × 0.2 × 0.15 mm
β = 109.745 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4593 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3602 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.988	R_int = 0.027
15313 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.28 e Å⁻³
4593 reflections	Δρ_min = −0.20 e Å⁻³
266 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
O5	0.66512 (9)	0.67514 (10)	0.46869 (8)	0.0399 (3)
O2	0.05682 (10)	0.56346 (9)	0.19250 (8)	0.0364 (3)
N1	−0.12494 (11)	0.70015 (10)	0.40319 (9)	0.0314 (3)
H1	−0.1795 (16)	0.6891 (14)	0.4328 (12)	0.037 (5)*
O3	0.03829 (10)	0.94192 (9)	0.23298 (7)	0.0334 (3)
O4	−0.04968 (10)	1.01757 (8)	0.32887 (7)	0.0345 (3)
C13	−0.10344 (19)	1.20435 (14)	0.33222 (14)	0.0474 (4)
H13A	−0.1056	1.2765	0.3036	0.071*
H13B	−0.0550	1.2090	0.3985	0.071*
H13C	−0.1891	1.1807	0.3241	0.071*
N2	0.53871 (11)	0.64292 (10)	0.55364 (9)	0.0285 (3)
H2	0.5381 (15)	0.6217 (14)	0.6074 (13)	0.037 (5)*
C1	0.03998 (12)	0.72957 (11)	0.30406 (10)	0.0249 (3)
H1A	0.0423	0.7441	0.2404	0.030*
C2	−0.03113 (12)	0.62288 (12)	0.30116 (10)	0.0281 (3)
O1	−0.05548 (11)	0.44057 (10)	0.23947 (9)	0.0455 (3)
C3	−0.10251 (13)	0.61059 (12)	0.35593 (11)	0.0304 (3)
C4	−0.10146 (12)	0.80695 (12)	0.38358 (10)	0.0274 (3)
C20	0.65040 (13)	0.64295 (12)	0.54023 (10)	0.0291 (3)
C17	0.41948 (12)	0.67243 (11)	0.48949 (10)	0.0259 (3)
C18	0.39430 (13)	0.67984 (14)	0.39484 (11)	0.0334 (3)
H18	0.4597	0.6700	0.3699	0.040*
C19	0.27293 (13)	0.70175 (13)	0.33631 (10)	0.0312 (3)
H19	0.2568	0.7066	0.2714	0.037*
C14	0.17503 (12)	0.71665 (11)	0.36981 (10)	0.0248 (3)
C8	−0.01382 (13)	0.53303 (13)	0.24354 (10)	0.0318 (3)
C9	0.08124 (17)	0.47931 (15)	0.13380 (12)	0.0435 (4)
H9A	0.0033	0.4608	0.0825	0.052*
H9B	0.1134	0.4120	0.1702	0.052*
C10	0.17680 (18)	0.52463 (18)	0.09623 (14)	0.0540 (5)
H10A	0.1950	0.4704	0.0553	0.081*
H10B	0.2538	0.5415	0.1476	0.081*
H10C	0.1443	0.5917	0.0611	0.081*
C6	−0.16499 (14)	0.89009 (13)	0.42459 (11)	0.0348 (3)
H6A	−0.2245	0.9327	0.3747	0.052*
H6B	−0.1021	0.9394	0.4654	0.052*
H6C	−0.2099	0.8525	0.4604	0.052*
C5	−0.02787 (12)	0.82421 (11)	0.33070 (9)	0.0251 (3)
C16	0.32309 (13)	0.69036 (14)	0.52466 (10)	0.0336 (3)
H16	0.3397	0.6877	0.5897	0.040*
C15	0.20282 (13)	0.71204 (14)	0.46516 (10)	0.0339 (3)
H15	0.1378	0.7240	0.4902	0.041*
C21	0.75834 (14)	0.59981 (14)	0.61983 (11)	0.0377 (4)
H21A	0.7863	0.5297	0.6023	0.057*
H21B	0.7316	0.5889	0.6737	0.057*
H21C	0.8275	0.6526	0.6354	0.057*
C11	−0.00926 (12)	0.93072 (12)	0.29325 (10)	0.0263 (3)
C12	−0.04350 (15)	1.12340 (12)	0.28729 (12)	0.0353 (3)
H12A	−0.0888	1.1209	0.2196	0.042*
H12B	0.0448	1.1440	0.2980	0.042*
C7	−0.16252 (16)	0.50641 (13)	0.37219 (13)	0.0410 (4)
H7A	−0.0973	0.4542	0.4058	0.062*
H7B	−0.2130	0.4747	0.3125	0.062*
H7C	−0.2165	0.5223	0.4089	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0260 (5)	0.0586 (8)	0.0404 (6)	0.0018 (5)	0.0182 (5)	0.0136 (5)
O2	0.0400 (6)	0.0352 (6)	0.0377 (6)	0.0008 (5)	0.0181 (5)	−0.0058 (5)
N1	0.0273 (6)	0.0348 (7)	0.0380 (7)	0.0011 (5)	0.0188 (5)	0.0062 (5)
O3	0.0403 (6)	0.0334 (6)	0.0346 (6)	−0.0017 (4)	0.0234 (5)	−0.0011 (4)
O4	0.0455 (6)	0.0290 (6)	0.0376 (6)	0.0042 (4)	0.0255 (5)	0.0030 (4)
C13	0.0610 (11)	0.0339 (9)	0.0562 (11)	0.0067 (8)	0.0315 (9)	0.0010 (8)
N2	0.0233 (6)	0.0373 (7)	0.0277 (6)	0.0016 (5)	0.0125 (5)	0.0060 (5)
C1	0.0226 (6)	0.0274 (7)	0.0273 (7)	0.0024 (5)	0.0117 (5)	0.0016 (5)
C2	0.0241 (6)	0.0275 (7)	0.0326 (8)	0.0015 (5)	0.0096 (6)	0.0035 (6)
O1	0.0494 (7)	0.0350 (7)	0.0528 (8)	−0.0080 (5)	0.0181 (6)	−0.0071 (5)
C3	0.0246 (7)	0.0304 (8)	0.0364 (8)	0.0011 (6)	0.0106 (6)	0.0051 (6)
C4	0.0222 (6)	0.0315 (8)	0.0299 (7)	0.0035 (5)	0.0109 (5)	0.0038 (6)
C20	0.0247 (7)	0.0307 (7)	0.0343 (8)	−0.0003 (5)	0.0132 (6)	0.0021 (6)
C17	0.0226 (6)	0.0274 (7)	0.0301 (7)	0.0009 (5)	0.0120 (5)	0.0031 (6)
C18	0.0255 (7)	0.0487 (9)	0.0314 (8)	0.0036 (6)	0.0168 (6)	0.0028 (7)
C19	0.0279 (7)	0.0427 (9)	0.0265 (7)	0.0022 (6)	0.0138 (6)	0.0036 (6)
C14	0.0236 (6)	0.0238 (7)	0.0297 (7)	0.0005 (5)	0.0125 (5)	0.0014 (5)
C8	0.0275 (7)	0.0323 (8)	0.0325 (8)	0.0005 (6)	0.0059 (6)	0.0007 (6)
C9	0.0536 (10)	0.0402 (9)	0.0345 (9)	0.0071 (8)	0.0122 (8)	−0.0084 (7)
C10	0.0478 (10)	0.0692 (13)	0.0484 (11)	0.0072 (9)	0.0207 (9)	−0.0147 (10)
C6	0.0343 (8)	0.0382 (9)	0.0394 (9)	0.0051 (6)	0.0224 (7)	0.0031 (7)
C5	0.0211 (6)	0.0281 (7)	0.0276 (7)	0.0022 (5)	0.0102 (5)	0.0016 (5)
C16	0.0284 (7)	0.0504 (10)	0.0258 (7)	0.0036 (6)	0.0145 (6)	0.0031 (6)
C15	0.0250 (7)	0.0510 (10)	0.0316 (8)	0.0053 (6)	0.0172 (6)	0.0013 (7)
C21	0.0269 (7)	0.0478 (10)	0.0389 (9)	0.0038 (6)	0.0117 (6)	0.0054 (7)
C11	0.0231 (6)	0.0310 (7)	0.0256 (7)	0.0009 (5)	0.0095 (5)	−0.0014 (6)
C12	0.0414 (8)	0.0292 (8)	0.0405 (9)	0.0000 (6)	0.0207 (7)	0.0028 (7)
C7	0.0382 (8)	0.0350 (9)	0.0555 (10)	−0.0041 (7)	0.0233 (8)	0.0058 (8)

Geometric parameters (Å, º) top

O5—C20	1.2278 (18)	C17—C16	1.3894 (19)
O2—C8	1.3469 (19)	C18—H18	0.9500
O2—C9	1.4515 (19)	C18—C19	1.391 (2)
N1—H1	0.893 (18)	C19—H19	0.9500
N1—C3	1.381 (2)	C19—C14	1.3833 (19)
N1—C4	1.3824 (19)	C14—C15	1.388 (2)
O3—C11	1.2244 (17)	C9—H9A	0.9900
O4—C11	1.3410 (17)	C9—H9B	0.9900
O4—C12	1.4513 (18)	C9—C10	1.494 (3)
C13—H13A	0.9800	C10—H10A	0.9800
C13—H13B	0.9800	C10—H10B	0.9800
C13—H13C	0.9800	C10—H10C	0.9800
C13—C12	1.492 (2)	C6—H6A	0.9800
N2—H2	0.867 (18)	C6—H6B	0.9800
N2—C20	1.3495 (18)	C6—H6C	0.9800
N2—C17	1.4230 (18)	C5—C11	1.464 (2)
C1—H1A	1.0000	C16—H16	0.9500
C1—C2	1.5231 (19)	C16—C15	1.386 (2)
C1—C14	1.5303 (18)	C15—H15	0.9500
C1—C5	1.5173 (18)	C21—H21A	0.9800
C2—C3	1.357 (2)	C21—H21B	0.9800
C2—C8	1.461 (2)	C21—H21C	0.9800
O1—C8	1.2157 (19)	C12—H12A	0.9900
C3—C7	1.501 (2)	C12—H12B	0.9900
C4—C6	1.499 (2)	C7—H7A	0.9800
C4—C5	1.3615 (19)	C7—H7B	0.9800
C20—C21	1.501 (2)	C7—H7C	0.9800
C17—C18	1.384 (2)

C8—O2—C9	116.13 (13)	O2—C9—H9B	110.3
C3—N1—H1	115.4 (11)	O2—C9—C10	107.00 (15)
C3—N1—C4	123.22 (12)	H9A—C9—H9B	108.6
C4—N1—H1	118.1 (11)	C10—C9—H9A	110.3
C11—O4—C12	116.72 (11)	C10—C9—H9B	110.3
H13A—C13—H13B	109.5	C9—C10—H10A	109.5
H13A—C13—H13C	109.5	C9—C10—H10B	109.5
H13B—C13—H13C	109.5	C9—C10—H10C	109.5
C12—C13—H13A	109.5	H10A—C10—H10B	109.5
C12—C13—H13B	109.5	H10A—C10—H10C	109.5
C12—C13—H13C	109.5	H10B—C10—H10C	109.5
C20—N2—H2	117.1 (11)	C4—C6—H6A	109.5
C20—N2—C17	128.01 (13)	C4—C6—H6B	109.5
C17—N2—H2	114.9 (11)	C4—C6—H6C	109.5
C2—C1—H1A	108.1	H6A—C6—H6B	109.5
C2—C1—C14	109.46 (11)	H6A—C6—H6C	109.5
C14—C1—H1A	108.1	H6B—C6—H6C	109.5
C5—C1—H1A	108.1	C4—C5—C1	120.71 (12)
C5—C1—C2	110.25 (11)	C4—C5—C11	124.68 (13)
C5—C1—C14	112.73 (11)	C11—C5—C1	114.59 (11)
C3—C2—C1	119.78 (13)	C17—C16—H16	119.9
C3—C2—C8	121.40 (13)	C15—C16—C17	120.17 (13)
C8—C2—C1	118.69 (12)	C15—C16—H16	119.9
N1—C3—C7	114.09 (13)	C14—C15—H15	119.2
C2—C3—N1	119.42 (13)	C16—C15—C14	121.56 (13)
C2—C3—C7	126.49 (14)	C16—C15—H15	119.2
N1—C4—C6	113.00 (12)	C20—C21—H21A	109.5
C5—C4—N1	118.48 (13)	C20—C21—H21B	109.5
C5—C4—C6	128.51 (13)	C20—C21—H21C	109.5
O5—C20—N2	123.61 (13)	H21A—C21—H21B	109.5
O5—C20—C21	121.22 (13)	H21A—C21—H21C	109.5
N2—C20—C21	115.17 (13)	H21B—C21—H21C	109.5
C18—C17—N2	123.52 (12)	O3—C11—O4	121.14 (13)
C18—C17—C16	119.06 (13)	O3—C11—C5	123.59 (13)
C16—C17—N2	117.37 (13)	O4—C11—C5	115.26 (12)
C17—C18—H18	120.1	O4—C12—C13	106.77 (13)
C17—C18—C19	119.83 (13)	O4—C12—H12A	110.4
C19—C18—H18	120.1	O4—C12—H12B	110.4
C18—C19—H19	119.0	C13—C12—H12A	110.4
C14—C19—C18	121.91 (13)	C13—C12—H12B	110.4
C14—C19—H19	119.0	H12A—C12—H12B	108.6
C19—C14—C1	121.24 (12)	C3—C7—H7A	109.5
C19—C14—C15	117.40 (13)	C3—C7—H7B	109.5
C15—C14—C1	121.21 (12)	C3—C7—H7C	109.5
O2—C8—C2	111.84 (13)	H7A—C7—H7B	109.5
O1—C8—O2	121.51 (14)	H7A—C7—H7C	109.5
O1—C8—C2	126.65 (15)	H7B—C7—H7C	109.5
O2—C9—H9A	110.3

C5—C1—C2—C3	−28.32 (18)	C9—O2—C8—C2	179.07 (12)
C14—C1—C2—C3	96.23 (15)	C3—C2—C8—O1	−2.2 (2)
C5—C1—C2—C8	155.75 (12)	C1—C2—C8—O1	173.71 (14)
C14—C1—C2—C8	−79.70 (15)	C3—C2—C8—O2	178.01 (13)
C8—C2—C3—N1	−174.57 (13)	C1—C2—C8—O2	−6.13 (18)
C1—C2—C3—N1	9.6 (2)	C8—O2—C9—C10	−170.92 (13)
C8—C2—C3—C7	5.6 (2)	N1—C4—C5—C11	170.85 (13)
C1—C2—C3—C7	−170.23 (14)	C6—C4—C5—C11	−8.3 (2)
C4—N1—C3—C2	14.1 (2)	N1—C4—C5—C1	−7.6 (2)
C4—N1—C3—C7	−166.00 (13)	C6—C4—C5—C1	173.31 (14)
C3—N1—C4—C5	−15.2 (2)	C2—C1—C5—C4	27.40 (18)
C3—N1—C4—C6	164.06 (13)	C14—C1—C5—C4	−95.25 (15)
C17—N2—C20—O5	3.8 (3)	C2—C1—C5—C11	−151.16 (12)
C17—N2—C20—C21	−175.95 (14)	C14—C1—C5—C11	86.19 (14)
C20—N2—C17—C18	17.1 (2)	C18—C17—C16—C15	1.9 (2)
C20—N2—C17—C16	−165.46 (15)	N2—C17—C16—C15	−175.64 (15)
C16—C17—C18—C19	−1.9 (2)	C17—C16—C15—C14	−0.1 (3)
N2—C17—C18—C19	175.51 (14)	C19—C14—C15—C16	−1.8 (2)
C17—C18—C19—C14	0.0 (2)	C1—C14—C15—C16	174.01 (14)
C18—C19—C14—C15	1.8 (2)	C12—O4—C11—O3	4.8 (2)
C18—C19—C14—C1	−173.97 (14)	C12—O4—C11—C5	−174.40 (12)
C5—C1—C14—C19	−133.47 (14)	C4—C5—C11—O3	−166.46 (14)
C2—C1—C14—C19	103.43 (15)	C1—C5—C11—O3	12.0 (2)
C5—C1—C14—C15	50.92 (18)	C4—C5—C11—O4	12.8 (2)
C2—C1—C14—C15	−72.17 (17)	C1—C5—C11—O4	−168.74 (11)
C9—O2—C8—O1	−0.8 (2)	C11—O4—C12—C13	175.03 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.892 (19)	2.022 (19)	2.8946 (17)	165.5 (16)
N2—H2···O3ⁱⁱ	0.866 (19)	2.074 (19)	2.9383 (17)	175.4 (16)
C6—H6A···O1ⁱⁱⁱ	0.98	2.52	3.370 (2)	145
C13—H13A···O1^iv	0.98	2.38	3.337 (2)	165

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x−1/2, y+1/2, −z+1/2; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆N₂O₅
M_r	386.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	11.3359 (7), 12.1934 (7), 15.3262 (9)
β (°)	109.745 (1)
V (Å³)	1993.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.2 × 0.2 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.976, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	15313, 4593, 3602
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.120, 1.05
No. of reflections	4593
No. of parameters	266
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.892 (19)	2.022 (19)	2.8946 (17)	165.5 (16)
N2—H2···O3ⁱⁱ	0.866 (19)	2.074 (19)	2.9383 (17)	175.4 (16)
C6—H6A···O1ⁱⁱⁱ	0.98	2.52	3.370 (2)	145
C13—H13A···O1^iv	0.98	2.38	3.337 (2)	165

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x−1/2, y+1/2, −z+1/2; (iv) x, y+1, z.

Acknowledgements

The authors would like to thank the Clive and Vera Ramaciotti Foundation for a generous equipment gift, and the National Health and Medical Research Council for funding.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kappe, C. O. & Stadler, A. (2004). Org. React. 63, 1–23. CAS Google Scholar
Kumar, A. & Maurya, R. A. (2008). Synlett, pp. 883–885. Web of Science CrossRef Google Scholar
Mobinikhaledi, A. & Foroughifar, N. (2006). Phosphorus Sulfur Silicon Relat. Elem. 181, 2653–2658. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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