1,5-Bis[(2-meth­oxy­eth­oxy)meth­yl]-1,5-naphthyridine-4,8(1H,5H)-dione

Wang, K.; Chen, C.; Jiang, P.; Shi, L.; Zhu, H.-J.

doi:10.1107/S1600536811054547

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o280

doi:10.1107/S1600536811054547

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1,5-Bis[(2-methoxyethoxy)methyl]-1,5-naphthyridine-4,8(1H,5H)-dione

Kunyan Wang,^a Chen Chen,^a Peng Jiang,^a Lu Shi ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 2 December 2011; accepted 19 December 2011; online 7 January 2012)

The complete molecule of the title compound, C₁₆H₂₂N₂O₆, is generated by crystallographic inversion symmetry. The conformation of the N—C—O—C fragment of the side chain is approximately gauche [torsion angle = −74.84 (17)°]. In the crystal, weak C—H⋯O interactions link the molecules.

Related literature

The background to the applications of the title compound, see: Shan et al. (2005 ). For the synthesis, see: Toshihiro et al. (2002 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₂₂N₂O₆
M_r = 338.36
Monoclinic, P 2₁ /n
a = 7.1610 (14) Å
b = 11.497 (2) Å
c = 10.734 (2) Å
β = 105.45 (3)°
V = 851.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.970, T_max = 0.990
3261 measured reflections
1549 independent reflections
1246 reflections with I > 2σ(I)
R_int = 0.047
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.140
S = 1.01
1549 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3ⁱ	0.93	2.45	3.264 (2)	147
C6—H6A⋯O1ⁱⁱ	0.93	2.58	3.397 (2)	147
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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, global. DOI: 10.1107/S1600536811054547/hb6550sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054547/hb6550Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054547/hb6550Isup3.cml

checkCIF report

Related literature top

The background to the applications of the title compound, see: Shan et al. (2005). For the synthesis, see: Toshihiro et al. (2002). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared by a method reported in literature (Toshihiro et al., 2002). Colourless blocks were obtained by dissolving it (0.5 g) in methanol (50 ml) and evaporating the solvent slowly at room temperature for about 30 d.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

1,5-Bis[(2-methoxyethoxy)methyl]-1,5-naphthyridine- 4,8(1H,5H)-dione top

Crystal data top

C₁₆H₂₂N₂O₆	F(000) = 360
M_r = 338.36	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 365 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.1610 (14) Å	Cell parameters from 25 reflections
b = 11.497 (2) Å	θ = 9–13°
c = 10.734 (2) Å	µ = 0.10 mm⁻¹
β = 105.45 (3)°	T = 293 K
V = 851.8 (3) Å³	Block, colourless
Z = 2	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1246 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.047
Graphite monochromator	θ_max = 25.3°, θ_min = 2.7°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
T_min = 0.970, T_max = 0.990	l = −12→12
3261 measured reflections	3 standard reflections every 200 reflections
1549 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.1P)² + 0.026P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1549 reflections	Δρ_max = 0.24 e Å⁻³
110 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.30 (2)

Crystal data top

C₁₆H₂₂N₂O₆	V = 851.8 (3) Å³
M_r = 338.36	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1610 (14) Å	µ = 0.10 mm⁻¹
b = 11.497 (2) Å	T = 293 K
c = 10.734 (2) Å	0.30 × 0.20 × 0.10 mm
β = 105.45 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1246 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.047
T_min = 0.970, T_max = 0.990	3 standard reflections every 200 reflections
3261 measured reflections	intensity decay: 1%
1549 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.01	Δρ_max = 0.24 e Å⁻³
1549 reflections	Δρ_min = −0.17 e Å⁻³
110 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
N1	0.03696 (18)	0.64646 (11)	0.57178 (12)	0.0421 (4)
O1	0.25472 (18)	1.00854 (10)	0.36603 (13)	0.0584 (4)
C1	0.2858 (3)	1.0712 (2)	0.2607 (2)	0.0781 (7)
H1A	0.2389	1.1492	0.2623	0.117*
H1B	0.2177	1.0341	0.1815	0.117*
H1C	0.4219	1.0729	0.2665	0.117*
O2	0.06007 (17)	0.80910 (9)	0.43882 (11)	0.0532 (4)
C5	0.1950 (2)	0.62630 (14)	0.67339 (15)	0.0479 (5)
H5A	0.2437	0.6875	0.7292	0.057*
C2	0.3185 (3)	0.89321 (17)	0.3692 (2)	0.0658 (6)
H2B	0.4581	0.8917	0.3836	0.079*
H2C	0.2603	0.8560	0.2869	0.079*
C3	0.2645 (3)	0.82888 (15)	0.4743 (2)	0.0639 (6)
H3A	0.3325	0.7551	0.4890	0.077*
H3B	0.3014	0.8736	0.5537	0.077*
O3	0.32189 (18)	0.33513 (10)	0.62397 (14)	0.0672 (5)
C4	−0.0118 (2)	0.77036 (13)	0.54011 (17)	0.0494 (5)
H4A	−0.1514	0.7797	0.5165	0.059*
H4B	0.0419	0.8177	0.6160	0.059*
C6	0.2837 (2)	0.52236 (14)	0.69674 (16)	0.0489 (5)
H6A	0.3860	0.5132	0.7704	0.059*
C7	0.2259 (2)	0.42641 (13)	0.61247 (15)	0.0449 (4)
C8	0.0437 (2)	0.44520 (12)	0.50952 (13)	0.0380 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0493 (7)	0.0351 (7)	0.0376 (7)	−0.0011 (5)	0.0041 (5)	−0.0016 (5)
O1	0.0678 (8)	0.0436 (7)	0.0690 (9)	0.0043 (5)	0.0273 (7)	0.0064 (5)
C1	0.0727 (13)	0.0781 (15)	0.0928 (16)	0.0075 (11)	0.0385 (12)	0.0289 (12)
O2	0.0602 (8)	0.0402 (6)	0.0513 (7)	−0.0052 (5)	0.0012 (6)	0.0059 (5)
C5	0.0557 (9)	0.0440 (9)	0.0374 (9)	−0.0068 (7)	0.0009 (7)	−0.0030 (6)
C2	0.0697 (11)	0.0493 (11)	0.0836 (14)	0.0087 (9)	0.0291 (10)	0.0052 (9)
C3	0.0577 (11)	0.0523 (11)	0.0756 (13)	0.0029 (8)	0.0071 (9)	0.0127 (9)
O3	0.0602 (8)	0.0429 (7)	0.0812 (10)	0.0086 (5)	−0.0114 (7)	0.0018 (6)
C4	0.0565 (9)	0.0341 (8)	0.0532 (10)	0.0014 (7)	0.0066 (7)	−0.0044 (7)
C6	0.0490 (9)	0.0464 (9)	0.0413 (9)	−0.0051 (7)	−0.0054 (7)	0.0051 (7)
C7	0.0459 (9)	0.0396 (8)	0.0446 (9)	0.0003 (7)	0.0040 (7)	0.0083 (7)
C8	0.0442 (8)	0.0341 (8)	0.0346 (8)	−0.0035 (6)	0.0086 (6)	0.0034 (6)

Geometric parameters (Å, º) top

N1—C5	1.366 (2)	C2—H2B	0.9700
N1—C8ⁱ	1.3919 (19)	C2—H2C	0.9700
N1—C4	1.4843 (19)	C3—H3A	0.9700
O1—C2	1.400 (2)	C3—H3B	0.9700
O1—C1	1.407 (2)	O3—C7	1.2426 (18)
C1—H1A	0.9600	C4—H4A	0.9700
C1—H1B	0.9600	C4—H4B	0.9700
C1—H1C	0.9600	C6—C7	1.417 (2)
O2—C4	1.394 (2)	C6—H6A	0.9300
O2—C3	1.429 (2)	C7—C8	1.484 (2)
C5—C6	1.345 (2)	C8—N1ⁱ	1.3919 (19)
C5—H5A	0.9300	C8—C8ⁱ	1.398 (3)
C2—C3	1.484 (3)

C5—N1—C8ⁱ	119.30 (13)	O2—C3—H3A	109.8
C5—N1—C4	116.10 (13)	C2—C3—H3A	109.8
C8ⁱ—N1—C4	123.37 (13)	O2—C3—H3B	109.8
C2—O1—C1	112.60 (16)	C2—C3—H3B	109.8
O1—C1—H1A	109.5	H3A—C3—H3B	108.2
O1—C1—H1B	109.5	O2—C4—N1	111.85 (13)
H1A—C1—H1B	109.5	O2—C4—H4A	109.2
O1—C1—H1C	109.5	N1—C4—H4A	109.2
H1A—C1—H1C	109.5	O2—C4—H4B	109.2
H1B—C1—H1C	109.5	N1—C4—H4B	109.2
C4—O2—C3	114.06 (14)	H4A—C4—H4B	107.9
C6—C5—N1	123.30 (15)	C5—C6—C7	121.98 (14)
C6—C5—H5A	118.3	C5—C6—H6A	119.0
N1—C5—H5A	118.3	C7—C6—H6A	119.0
O1—C2—C3	109.96 (17)	O3—C7—C6	122.30 (14)
O1—C2—H2B	109.7	O3—C7—C8	123.39 (14)
C3—C2—H2B	109.7	C6—C7—C8	114.30 (13)
O1—C2—H2C	109.7	N1ⁱ—C8—C8ⁱ	119.73 (16)
C3—C2—H2C	109.7	N1ⁱ—C8—C7	119.50 (13)
H2B—C2—H2C	108.2	C8ⁱ—C8—C7	120.73 (16)
O2—C3—C2	109.45 (16)

C8ⁱ—N1—C5—C6	2.9 (3)	N1—C5—C6—C7	3.7 (3)
C4—N1—C5—C6	−164.78 (16)	C5—C6—C7—O3	170.47 (16)
C1—O1—C2—C3	−174.45 (17)	C5—C6—C7—C8	−8.8 (2)
C4—O2—C3—C2	−167.81 (14)	O3—C7—C8—N1ⁱ	6.6 (2)
O1—C2—C3—O2	72.0 (2)	C6—C7—C8—N1ⁱ	−174.16 (14)
C3—O2—C4—N1	−74.84 (17)	O3—C7—C8—C8ⁱ	−171.19 (18)
C5—N1—C4—O2	97.84 (16)	C6—C7—C8—C8ⁱ	8.1 (2)
C8ⁱ—N1—C4—O2	−69.31 (19)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3ⁱⁱ	0.93	2.45	3.264 (2)	147
C6—H6A···O1ⁱⁱⁱ	0.93	2.58	3.397 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₂N₂O₆
M_r	338.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.1610 (14), 11.497 (2), 10.734 (2)
β (°)	105.45 (3)
V (Å³)	851.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.970, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3261, 1549, 1246
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.140, 1.01
No. of reflections	1549
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.17

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), 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
C5—H5A···O3ⁱ	0.93	2.45	3.264 (2)	147
C6—H6A···O1ⁱⁱ	0.93	2.58	3.397 (2)	147

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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