2-Eth­oxy­methyl-6-ethyl-2,3,4,5-tetra­hydro-1,2,4-triazine-3,5-dione

El-Brollosy, N.R.; El-Emam, A.A.; Al-Deeb, O.A.; Ng, S.W.

doi:10.1107/S1600536811055747

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o346

doi:10.1107/S1600536811055747

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2-Ethoxymethyl-6-ethyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione

Nasser R. El-Brollosy,^a Ali A. El-Emam,^a Omar A. Al-Deeb ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 December 2011; accepted 26 December 2011; online 11 January 2012)

The 1,2,4-triazine ring of the title compound, C₈H₁₃N₃O₃, is nearly planar (r.m.s. deviation = 0.019 Å). The imino group is hydrogen-bond donor to the exocyclic O atom at the 5-position of an adjacent molecule, the N—H⋯O hydrogen bond generating a chain parallel to the b axis.

Related literature

For the synthesis, see: El-Brollosy (2008 ).

Experimental

Crystal data

C₈H₁₃N₃O₃
M_r = 199.21
Monoclinic, C 2/c
a = 20.4078 (19) Å
b = 4.4343 (3) Å
c = 22.6285 (17) Å
β = 111.813 (10)°
V = 1901.1 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.35 × 0.25 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.963, T_max = 0.984
3623 measured reflections
2174 independent reflections
1739 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.06
2174 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.89 (2)	1.95 (2)	2.837 (2)	174.1 (17)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055747/xu5421sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055747/xu5421Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055747/xu5421Isup3.cml

checkCIF report

Comment top

The compound (Scheme I) was synthesized for an evaluation of its anti-microbial properties (El-Brollosy, 2008). The 1,2,4-triazine ring is planar; the C atom at the 6-position deviates by 0.155 (2) Å from the mean plane whereas the C atom at the 2-position deviates from the mean plane by 0.081 (2) Å in the opposite direction (Fig. 1). The amino group is hydrogen-bond donor to the exocyclic O atom at the 5-position, the hydrogen bond generating a linear chain parallel to the b-axis of the monoclinc unit cell (Table 1, Fig. 2).

Related literature top

For the synthesis, see: El-Brollosy (2008).

Experimental top

The compound was synthesized by using a reported method (El-Brollosy, 2008), and was recrystallized from ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₈H₁₃N₃O₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain structure.

2-Ethoxymethyl-6-ethyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione top

Crystal data top

C₈H₁₃N₃O₃	F(000) = 848
M_r = 199.21	D_x = 1.392 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1592 reflections
a = 20.4078 (19) Å	θ = 2.3–27.5°
b = 4.4343 (3) Å	µ = 0.11 mm⁻¹
c = 22.6285 (17) Å	T = 100 K
β = 111.813 (10)°	Prism, colorless
V = 1901.1 (3) Å³	0.35 × 0.25 × 0.15 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2174 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1739 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.4°
ω scan	h = −26→26
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→5
T_min = 0.963, T_max = 0.984	l = −15→29
3623 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0432P)² + 1.2698P] where P = (F_o² + 2F_c²)/3
2174 reflections	(Δ/σ)_max = 0.001
131 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₈H₁₃N₃O₃	V = 1901.1 (3) Å³
M_r = 199.21	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.4078 (19) Å	µ = 0.11 mm⁻¹
b = 4.4343 (3) Å	T = 100 K
c = 22.6285 (17) Å	0.35 × 0.25 × 0.15 mm
β = 111.813 (10)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2174 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1739 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.984	R_int = 0.023
3623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.31 e Å⁻³
2174 reflections	Δρ_min = −0.28 e Å⁻³
131 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.73492 (5)	0.9252 (3)	0.68461 (5)	0.0201 (3)
O2	0.58065 (6)	0.2354 (3)	0.70746 (5)	0.0214 (3)
O3	0.42473 (5)	0.6126 (2)	0.59416 (5)	0.0172 (3)
N1	0.65902 (7)	0.5753 (3)	0.69639 (6)	0.0152 (3)
N2	0.56241 (6)	0.7358 (3)	0.57988 (6)	0.0138 (3)
N3	0.54722 (6)	0.5285 (3)	0.61778 (5)	0.0144 (3)
C1	0.67786 (7)	0.7953 (3)	0.66355 (7)	0.0141 (3)
C2	0.62375 (7)	0.8617 (3)	0.59987 (6)	0.0130 (3)
C3	0.64247 (8)	1.0709 (3)	0.55670 (7)	0.0159 (3)
H3A	0.6664	1.2510	0.5810	0.019*
H3B	0.5987	1.1387	0.5221	0.019*
C4	0.69101 (8)	0.9188 (4)	0.52750 (7)	0.0197 (3)
H4A	0.7019	1.0617	0.4994	0.030*
H4B	0.6672	0.7418	0.5029	0.030*
H4C	0.7349	0.8559	0.5616	0.030*
C5	0.59417 (8)	0.4319 (3)	0.67624 (7)	0.0152 (3)
C6	0.47519 (8)	0.4069 (3)	0.59096 (7)	0.0167 (3)
H6A	0.4642	0.3508	0.5459	0.020*
H6B	0.4726	0.2216	0.6144	0.020*
C7	0.42810 (8)	0.6726 (4)	0.65804 (7)	0.0200 (3)
H7A	0.4709	0.7914	0.6818	0.024*
H7B	0.4300	0.4809	0.6810	0.024*
C8	0.36268 (9)	0.8478 (4)	0.65258 (8)	0.0252 (4)
H8A	0.3635	0.8925	0.6953	0.038*
H8B	0.3207	0.7277	0.6292	0.038*
H8C	0.3614	1.0369	0.6298	0.038*
H1	0.6913 (10)	0.515 (4)	0.7331 (9)	0.024 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0179 (6)	0.0261 (6)	0.0138 (5)	−0.0056 (5)	0.0028 (4)	−0.0018 (4)
O2	0.0237 (6)	0.0226 (6)	0.0166 (5)	−0.0020 (5)	0.0059 (4)	0.0063 (5)
O3	0.0153 (5)	0.0246 (6)	0.0112 (5)	0.0001 (5)	0.0043 (4)	−0.0008 (4)
N1	0.0148 (6)	0.0179 (7)	0.0095 (6)	0.0019 (5)	0.0007 (5)	0.0013 (5)
N2	0.0168 (6)	0.0133 (6)	0.0118 (6)	0.0010 (5)	0.0059 (5)	0.0008 (5)
N3	0.0141 (6)	0.0171 (6)	0.0102 (6)	−0.0017 (5)	0.0026 (5)	0.0019 (5)
C1	0.0146 (7)	0.0161 (7)	0.0115 (7)	0.0006 (6)	0.0047 (5)	−0.0019 (6)
C2	0.0153 (7)	0.0126 (7)	0.0110 (7)	0.0019 (6)	0.0048 (5)	−0.0006 (6)
C3	0.0183 (7)	0.0149 (7)	0.0138 (7)	−0.0010 (6)	0.0049 (6)	0.0006 (6)
C4	0.0205 (8)	0.0245 (8)	0.0153 (7)	−0.0030 (7)	0.0081 (6)	−0.0011 (6)
C5	0.0171 (7)	0.0163 (7)	0.0121 (7)	0.0027 (6)	0.0054 (6)	0.0001 (6)
C6	0.0159 (7)	0.0188 (8)	0.0141 (7)	−0.0035 (6)	0.0039 (6)	−0.0015 (6)
C7	0.0246 (8)	0.0243 (8)	0.0118 (7)	−0.0063 (7)	0.0075 (6)	−0.0017 (6)
C8	0.0254 (9)	0.0310 (9)	0.0226 (8)	−0.0068 (8)	0.0127 (7)	−0.0089 (7)

Geometric parameters (Å, º) top

O1—C1	1.2256 (18)	C3—H3A	0.9900
O2—C5	1.2164 (18)	C3—H3B	0.9900
O3—C6	1.3974 (18)	C4—H4A	0.9800
O3—C7	1.4461 (17)	C4—H4B	0.9800
N1—C1	1.3654 (19)	C4—H4C	0.9800
N1—C5	1.3839 (19)	C6—H6A	0.9900
N1—H1	0.889 (19)	C6—H6B	0.9900
N2—C2	1.2894 (19)	C7—C8	1.509 (2)
N2—N3	1.3688 (16)	C7—H7A	0.9900
N3—C5	1.3821 (18)	C7—H7B	0.9900
N3—C6	1.4686 (19)	C8—H8A	0.9800
C1—C2	1.4832 (19)	C8—H8B	0.9800
C2—C3	1.496 (2)	C8—H8C	0.9800
C3—C4	1.536 (2)

C6—O3—C7	114.18 (11)	H4A—C4—H4C	109.5
C1—N1—C5	125.26 (13)	H4B—C4—H4C	109.5
C1—N1—H1	117.7 (12)	O2—C5—N3	123.49 (14)
C5—N1—H1	117.0 (12)	O2—C5—N1	122.24 (13)
C2—N2—N3	119.17 (12)	N3—C5—N1	114.26 (13)
N2—N3—C5	124.75 (12)	O3—C6—N3	112.50 (12)
N2—N3—C6	114.37 (11)	O3—C6—H6A	109.1
C5—N3—C6	120.88 (12)	N3—C6—H6A	109.1
O1—C1—N1	122.90 (13)	O3—C6—H6B	109.1
O1—C1—C2	122.78 (13)	N3—C6—H6B	109.1
N1—C1—C2	114.33 (12)	H6A—C6—H6B	107.8
N2—C2—C1	122.02 (13)	O3—C7—C8	107.51 (12)
N2—C2—C3	119.31 (12)	O3—C7—H7A	110.2
C1—C2—C3	118.61 (13)	C8—C7—H7A	110.2
C2—C3—C4	111.76 (12)	O3—C7—H7B	110.2
C2—C3—H3A	109.3	C8—C7—H7B	110.2
C4—C3—H3A	109.3	H7A—C7—H7B	108.5
C2—C3—H3B	109.3	C7—C8—H8A	109.5
C4—C3—H3B	109.3	C7—C8—H8B	109.5
H3A—C3—H3B	107.9	H8A—C8—H8B	109.5
C3—C4—H4A	109.5	C7—C8—H8C	109.5
C3—C4—H4B	109.5	H8A—C8—H8C	109.5
H4A—C4—H4B	109.5	H8B—C8—H8C	109.5
C3—C4—H4C	109.5

C2—N2—N3—C5	−2.5 (2)	C1—C2—C3—C4	74.86 (17)
C2—N2—N3—C6	178.28 (12)	N2—N3—C5—O2	−175.83 (13)
C5—N1—C1—O1	176.71 (14)	C6—N3—C5—O2	3.3 (2)
C5—N1—C1—C2	−4.0 (2)	N2—N3—C5—N1	3.3 (2)
N3—N2—C2—C1	−1.8 (2)	C6—N3—C5—N1	−177.56 (12)
N3—N2—C2—C3	175.47 (12)	C1—N1—C5—O2	179.42 (14)
O1—C1—C2—N2	−175.88 (14)	C1—N1—C5—N3	0.3 (2)
N1—C1—C2—N2	4.8 (2)	C7—O3—C6—N3	−68.72 (15)
O1—C1—C2—C3	6.9 (2)	N2—N3—C6—O3	−74.79 (15)
N1—C1—C2—C3	−172.48 (12)	C5—N3—C6—O3	106.00 (15)
N2—C2—C3—C4	−102.47 (16)	C6—O3—C7—C8	−169.27 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (2)	1.95 (2)	2.837 (2)	174.1 (17)

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

Experimental details

Crystal data
Chemical formula	C₈H₁₃N₃O₃
M_r	199.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	20.4078 (19), 4.4343 (3), 22.6285 (17)
β (°)	111.813 (10)
V (Å³)	1901.1 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.963, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3623, 2174, 1739
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.06
No. of reflections	2174
No. of parameters	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (2)	1.95 (2)	2.837 (2)	174.1 (17)

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

Acknowledgements

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, and the University of Malaya for supporting this study.

References

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