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In the title compound, C18H21NO4, the mol­ecules form dimers by means of a pair of N—H...O hydrogen bonds. The 2(1H)-pyridone ring displays a screw–boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001624/na6197sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001624/na6197Isup2.hkl
Contains datablock I

CCDC reference: 204715

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.067
  • wR factor = 0.219
  • Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
SHFSU_01 Alert B The absolute value of parameter shift to su ratio > 0.10 Absolute value of the parameter shift to su ratio given 0.110 Additional refinement cycles may be required.
Yellow Alert Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.620 Test value = 0.600 DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54184 REFLT_03 From the CIF: _diffrn_reflns_theta_max 69.11 From the CIF: _reflns_number_total 2962 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3172 Completeness (_total/calc) 93.38% Alert C: < 95% complete WEIGH_01 Alert C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc' Weighting scheme identified as calc PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(33) - C(34) = 1.41 Ang.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
6 Alert Level C = Please check

Comment top

A wide variety of compounds containing the 2(1H)-pyridone ring are found in nature and in some cases they diplay useful biological properties (Overman et al., 1980). 2(1H)-Pyridones are very close in structure to the 1,4-dihidropyridines, which have been used as effective drugs in the treatment of cardiovascular diseases. In a previous work, we have reported a general procedure (Verdecia et al., 1996) for the synthesis of novel o-chloroformyl-substituted ethyl 1,4-dihydropyridine-5-carboxylates from the corresponding 3,4-dihydropyridone (Goldmann & Stoltefuss, 1991). The reaction proceeds through a mechanism involving several steps and one of the intermediate formed in the reaction is the title compound, (I).

The 2(1H)-pyridone ring of (I) has a screw–boat conformation, with puckering parameters (Cremer & Pople, 1975) Q = 0.280 (2) Å, θ = 109.5 (4)° and ϕ = 339.1 (5)°, with the axis through C2—C3, for N1—C1—C2—C3—C4—C5—C6. The dihedral angle between the least-squares planes of the phenyl ring and the pyridone moiety is 86.0 (1)°. The mean Csp2—Csp2 bond length within this ring is 1.434 (1) Å. An N—H···O hydrogen bond holds the molecules together in a dimeric association (Table 2).

Experimental top

The title compund was prepared by stirring a solution of 5-ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydro-2(1H)-pyridone (10 mmol) in anhydrous N,N-dimethylformamide (40 mmol), and phosphorus oxychloride (40 mmol) in dry chloroform (50 ml). After stirring at room temperature for 18 h, 20 ml of anhydrous ethanol was added. After 0.5 h, a white solid had precipitated and was filtered off. Further purification was accomplished by recrystallization from methanol (yield 68%; m.p. 746–747 K). IR (KBr, cm−1): 3202 (NH), 1697 (CO), 1674 (CO), 1637 (CC); 1H NMR (DMSO-δ6, p.p.m.): 9.68 (s, 1H, NH), 7.36 (s, 1H, CH), 7.31–7.11 (m, 5H, Ph), 4.89 (s, 1H, H-4), 4.13 (q, 2H, CH2), 3.96 (q, 2H, CH2), 2.29 (s, 3H, CH3), 1.22 (t, 3H, CH3), 1.06 (t, 3H, CH3); 13C NMR (DMSO-δ6, p.p.m.): 171.4 (C2), 169.7 (COO), 161.2 (CH), 152.2 (C6), 149.5 (C1'), 133.4 (C2', C6'), 131.9 (C3', C5'), 131.4 (C4'), 114.5 (C3), 109.2 (C5), 75.3 (CH2), 64.5 (CH2), 43.4 (C4), 23.5 (CH3), 20.5 (CH3), 19.3 (CH3); MS: m/Z (intensity%): 315 (M+, 64), 286 (60), 270 (31), 238 (65), 210 (100), 182 (44). Crystals suitable for X-ray analysis were obtained by slow evaporation from methanol.

Refinement top

H atoms were calculated geometrically and included in the refinement, but were restrained to ride on their parent atoms. The isotropic displacement parameters of the H atoms were fixed at 1.3Ueq of their parent atoms.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 1990), PARST (Nardelli, 1995) and PARSTCIF (Nardelli, 1991).

Figures top
[Figure 1] Fig. 1. Plot showing the atomic numbering scheme in (I). Displacement ellipsoids are drawn at 50% probability level for non-H atoms.
Ethyl 5-ethoxymethylene-2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3- carboxylate top
Crystal data top
C18H21NO4F(000) = 1344
Mr = 315.36Dx = 1.230 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
a = 22.652 (1) ÅCell parameters from 40 reflections
b = 10.5508 (3) Åθ = 10.8–27.9°
c = 15.7162 (7) ŵ = 0.71 mm1
β = 114.921 (4)°T = 293 K
V = 3406.4 (3) Å3Prism, colourless
Z = 80.60 × 0.40 × 0.40 mm
Data collection top
Siemens P4 four-circle
diffractometer
Rint = 0.030
ω/2θ scansθmax = 69.1°
Absorption correction: ψ scan
(North et al., 1968)
h = 127
Tmin = 0.565, Tmax = 0.753k = 112
7611 measured reflectionsl = 1917
2962 independent reflections3 standard reflections every 100 reflections
2690 reflections with F2 > 2σ(F2) intensity decay: 0.0%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: fullCalculated' w = 1/[σ2(Fo2) + (0.1525P)2 + 3.0912P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.067(Δ/σ)max = 0.110
wR(F2) = 0.219Δρmax = 0.62 e Å3
S = 0.98Δρmin = 0.39 e Å3
2962 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin((2θ)]-1/4
212 parametersExtinction coefficient: 0.0018 (3)
Crystal data top
C18H21NO4V = 3406.4 (3) Å3
Mr = 315.36Z = 8
Monoclinic, C2/cCu Kα radiation
a = 22.652 (1) ŵ = 0.71 mm1
b = 10.5508 (3) ÅT = 293 K
c = 15.7162 (7) Å0.60 × 0.40 × 0.40 mm
β = 114.921 (4)°
Data collection top
Siemens P4 four-circle
diffractometer
2690 reflections with F2 > 2σ(F2)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.030
Tmin = 0.565, Tmax = 0.7533 standard reflections every 100 reflections
7611 measured reflections intensity decay: 0.0%
2962 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.219(Δ/σ)max = 0.110
S = 0.98Δρmax = 0.62 e Å3
2962 reflectionsΔρmin = 0.39 e Å3
212 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.04183 (9)0.4236 (2)0.11740 (10)0.0497 (7)*
C20.00800 (10)0.3230 (2)0.0642 (2)0.0458 (8)*
O210.02680 (9)0.3385 (2)0.02010 (10)0.0600 (7)*
C30.01580 (10)0.2040 (2)0.11450 (10)0.0418 (7)*
C310.02890 (10)0.1150 (2)0.0729 (2)0.0468 (8)*
O320.02744 (8)0.0026 (2)0.11370 (10)0.0567 (7)*
C330.0839 (2)0.0762 (3)0.0651 (2)0.0790 (10)*
C340.0779 (3)0.1899 (4)0.1154 (3)0.120 (3)*
C40.07280 (10)0.1869 (2)0.20980 (10)0.0406 (8)*
C1'0.12890 (10)0.1215 (2)0.19700 (10)0.0426 (8)*
C2'0.13090 (10)0.0103 (2)0.1940 (2)0.0574 (9)*
C3'0.1789 (2)0.0711 (3)0.1768 (2)0.0720 (10)*
C4'0.22530 (10)0.0025 (3)0.1627 (2)0.0750 (10)*
C5'0.22430 (10)0.1273 (3)0.1663 (2)0.0700 (10)*
C6'0.17630 (10)0.1893 (2)0.1833 (2)0.0550 (10)*
C50.09230 (10)0.3116 (2)0.26190 (10)0.0410 (8)*
C510.13120 (10)0.2965 (2)0.3636 (2)0.0447 (8)*
O520.15067 (9)0.1948 (2)0.39910 (10)0.0612 (7)*
O530.14382 (9)0.4028 (2)0.41410 (10)0.0619 (7)*
C540.1836 (2)0.3895 (3)0.5142 (2)0.0730 (10)*
C550.1992 (3)0.5173 (4)0.5544 (2)0.127 (2)*
C60.07680 (10)0.4228 (2)0.2147 (2)0.0443 (8)*
C610.09320 (10)0.5550 (2)0.2530 (2)0.0640 (10)*
H10.04150.4930.08850.06*
H310.0620.13120.0140.056*
H33A0.12290.03140.05910.095*
H33B0.08780.09530.00260.095*
H34A0.03550.22570.13180.18*
H34B0.11060.24890.07720.18*
H34C0.08350.17250.17150.18*
H40.05860.13020.24690.049*
H2'0.09970.05790.20370.069*
H3'0.17970.15920.17480.086*
H4'0.25730.04360.15060.09*
H5'0.2560.17410.15740.084*
H6'0.17610.27740.18550.066*
H54A0.22320.34370.52510.088*
H54B0.160.34290.54320.088*
H55A0.23080.51170.61840.153*
H55B0.16040.55690.5520.153*
H55C0.21660.56670.5190.153*
H61A0.10050.60750.20840.095*
H61B0.13180.55320.31080.095*
H61C0.05780.58880.26410.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0500 (10)0.0430 (10)0.0420 (10)0.0014 (8)0.0049 (8)0.0041 (7)
C20.0390 (10)0.0490 (10)0.0380 (10)0.0027 (9)0.0062 (9)0.0015 (9)
O210.0620 (10)0.0553 (9)0.0401 (8)0.0021 (8)0.0010 (7)0.0049 (7)
C30.0330 (10)0.0450 (10)0.0390 (10)0.0009 (9)0.0070 (8)0.0009 (8)
C310.0410 (10)0.0500 (10)0.0390 (10)0.0010 (10)0.0064 (9)0.0021 (9)
O320.0510 (10)0.0540 (10)0.0475 (9)0.0142 (8)0.0034 (7)0.0008 (7)
C330.083 (2)0.071 (2)0.063 (2)0.036 (2)0.0090 (10)0.0040 (10)
C340.167 (5)0.087 (3)0.091 (3)0.054 (3)0.038 (3)0.002 (2)
C40.0340 (10)0.0430 (10)0.0360 (10)0.0022 (8)0.0069 (8)0.0017 (8)
C1'0.0360 (10)0.0450 (10)0.0350 (10)0.0058 (9)0.0032 (8)0.0019 (8)
C2'0.055 (2)0.0460 (10)0.0580 (10)0.0060 (10)0.0110 (10)0.0020 (10)
C3'0.070 (2)0.057 (2)0.068 (2)0.0240 (10)0.0090 (10)0.0050 (10)
C4'0.054 (2)0.089 (2)0.072 (2)0.026 (2)0.0160 (10)0.011 (2)
C5'0.047 (2)0.085 (2)0.077 (2)0.0050 (10)0.0250 (10)0.005 (2)
C6'0.0430 (10)0.0550 (10)0.0620 (10)0.0010 (10)0.0180 (10)0.0030 (10)
C50.0310 (10)0.0470 (10)0.0380 (10)0.0014 (8)0.0085 (9)0.0016 (8)
C510.0330 (10)0.0540 (10)0.0400 (10)0.0000 (9)0.0085 (9)0.0013 (9)
O520.0590 (10)0.0580 (10)0.0456 (9)0.0050 (8)0.0023 (8)0.0063 (7)
O530.0680 (10)0.0610 (10)0.0378 (8)0.0027 (9)0.0044 (7)0.0066 (7)
C540.077 (2)0.079 (2)0.0380 (10)0.004 (2)0.0000 (10)0.0050 (10)
C550.171 (4)0.102 (3)0.054 (2)0.007 (3)0.006 (2)0.025 (2)
C60.0340 (10)0.0460 (10)0.0430 (10)0.0018 (9)0.0065 (9)0.0029 (8)
C610.061 (2)0.0450 (10)0.0580 (10)0.0070 (10)0.0000 (10)0.0060 (10)
Geometric parameters (Å, º) top
O21—C21.234 (3)C33—C341.411 (5)
O32—C311.342 (3)C54—C551.468 (5)
O32—C331.445 (4)C2'—H2'0.93
O52—C511.204 (3)C3'—H3'0.93
O53—C511.333 (3)C4—H40.98
O53—C541.453 (3)C4'—H4'0.93
N1—C21.368 (3)C5'—H5'0.93
N1—C61.394 (3)C6'—H6'0.93
N1—H10.86C31—H310.93
C1'—C2'1.393 (3)C33—H33A0.97
C1'—C6'1.380 (4)C33—H33B0.97
C1'—C41.531 (3)C34—H34A0.96
C2—C31.454 (3)C34—H34B0.96
C2'—C3'1.385 (5)C34—H34C0.96
C3—C41.522 (3)C54—H54A0.97
C3—C311.332 (3)C54—H54B0.97
C3'—C4'1.369 (5)C55—H55A0.96
C4—C51.514 (3)C55—H55B0.96
C4'—C5'1.371 (4)C55—H55C0.96
C5—C511.473 (3)C61—H61A0.96
C5—C61.353 (3)C61—H61B0.96
C5'—C6'1.388 (4)C61—H61C0.96
C6—C611.502 (3)
C31—O32—C33114.7 (2)C3—C4—H4108
C51—O53—C54116.3 (2)C5—C4—H4108
C2—N1—C6125.4 (2)C3'—C4'—H4'120
C6—N1—H1117C5'—C4'—H4'120
C2—N1—H1117C4'—C5'—H5'120
C4—C1'—C6'122.0 (2)C6'—C5'—H5'120
C2'—C1'—C6'118.3 (2)C1'—C6'—H6'120
C2'—C1'—C4119.6 (2)C5'—C6'—H6'120
O21—C2—N1119.6 (2)O32—C31—H31119
O21—C2—C3125.0 (2)C3—C31—H31119
N1—C2—C3115.4 (2)O32—C33—H33A110
C1'—C2'—C3'120.6 (3)O32—C33—H33B110
C4—C3—C31123.6 (2)C34—C33—H33A110
C2—C3—C4119.7 (2)C34—C33—H33B110
C2—C3—C31116.7 (2)H33A—C33—H33B108
C2'—C3'—C4'120.5 (3)C33—C34—H34A110
C3—C4—C5111.2 (2)C33—C34—H34B110
C1'—C4—C3109.3 (2)C33—C34—H34C110
C1'—C4—C5113.2 (2)H34A—C34—H34B110
C3'—C4'—C5'119.6 (3)H34A—C34—H34C110
C6—C5—C51126.0 (2)H34B—C34—H34C109
C4—C5—C51113.4 (2)O53—C54—H54A110
C4—C5—C6120.5 (2)O53—C54—H54B110
C4'—C5'—C6'120.5 (3)C55—C54—H54A110
C5—C6—C61128.5 (2)C55—C54—H54B110
N1—C6—C5120.2 (2)H54A—C54—H54B108
N1—C6—C61111.3 (2)C54—C55—H55A110
C1'—C6'—C5'120.6 (2)C54—C55—H55B109
O32—C31—C3121.9 (2)C54—C55—H55C109
O32—C33—C34109.8 (3)H55A—C55—H55B110
O52—C51—O53122.0 (2)H55A—C55—H55C110
O52—C51—C5122.3 (2)H55B—C55—H55C110
O53—C51—C5115.8 (2)C6—C61—H61A110
O53—C54—C55107.7 (2)C6—C61—H61B110
C1'—C2'—H2'120C6—C61—H61C110
C3'—C2'—H2'120H61A—C61—H61B110
C2'—C3'—H3'120H61A—C61—H61C110
C4'—C3'—H3'120H61B—C61—H61C110
C1'—C4—H4108
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O21i0.862.032.885 (3)171
C31—H31···O210.932.462.785 (3)100
C61—H61B···O530.962.202.803 (3)119
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC18H21NO4
Mr315.36
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)22.652 (1), 10.5508 (3), 15.7162 (7)
β (°) 114.921 (4)
V3)3406.4 (3)
Z8
Radiation typeCu Kα
µ (mm1)0.71
Crystal size (mm)0.60 × 0.40 × 0.40
Data collection
DiffractometerSiemens P4 four-circle
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.565, 0.753
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
7611, 2962, 2690
Rint0.030
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.219, 0.98
No. of reflections2962
No. of parameters212
No. of restraints?
H-atom treatmentH-atom parameters constrained
(Δ/σ)max0.110
Δρmax, Δρmin (e Å3)0.62, 0.39

Computer programs: XSCANS (Siemens, 1996), XSCANS, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PLATON (Spek, 1990), PARST (Nardelli, 1995) and PARSTCIF (Nardelli, 1991).

Selected geometric parameters (Å, º) top
O21—C21.234 (3)O53—C511.333 (3)
O32—C311.342 (3)O53—C541.453 (3)
O32—C331.445 (4)N1—C21.368 (3)
O52—C511.204 (3)N1—C61.394 (3)
C31—O32—C33114.7 (2)N1—C6—C61111.3 (2)
C51—O53—C54116.3 (2)O32—C31—C3121.9 (2)
C2—N1—C6125.4 (2)O32—C33—C34109.8 (3)
O21—C2—N1119.6 (2)O52—C51—O53122.0 (2)
O21—C2—C3125.0 (2)O52—C51—C5122.3 (2)
N1—C2—C3115.4 (2)O53—C51—C5115.8 (2)
N1—C6—C5120.2 (2)O53—C54—C55107.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O21i0.862.032.885 (3)171
C31—H31···O210.932.462.785 (3)100
C61—H61B···O530.962.202.803 (3)119
Symmetry code: (i) x, y+1, z.
 

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