2-{[(2-Methyl­prop-2-en-1-yl)­oxy]meth­yl}-6-phenyl-2,3,4,5-tetra­hydro-1,2,4-triazine-3,5-dione

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

doi:10.1107/S160053681105567X

organic compounds

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Volume 68| Part 2| February 2012| Page o347

doi:10.1107/S160053681105567X

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2-{[(2-Methylprop-2-en-1-yl)oxy]methyl}-6-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione

Nasser R. El-Brollosy,^a Ali A. El-Emam,^a Abdulghafoor A. Al-Turkistani ^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 in the title compound, C₁₄H₁₅N₃O₃, is approximately planar (r.m.s. deviation = 0.019 Å); the C atom at the 6-position deviates by 0.026 (2) Å from the mean plane whereas the C atom at the 2-position deviates by 0.166 (4) Å in the opposite direction. The triazine ring is oriented at 8.60 (13)° with respect to the phenyl ring. The imino group is hydrogen-bond donor to the exocyclic O atom at the 3-position of an adjacent molecule, the hydrogen bond generating an inversion dimer.

Related literature

For the synthesis and antimicrobial activity of the title compound, see: El-Brollosy (2008 ).

Experimental

Crystal data

C₁₄H₁₅N₃O₃
M_r = 273.29
Triclinic, $[P \overline 1]$
a = 4.6162 (5) Å
b = 11.7896 (14) Å
c = 12.5769 (10) Å
α = 81.588 (8)°
β = 85.836 (7)°
γ = 87.245 (9)°
V = 674.84 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.30 × 0.03 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.972, T_max = 0.997
9875 measured reflections
3088 independent reflections
1878 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.250
S = 1.01
3088 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.45 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 (1)	1.93 (1)	2.802 (3)	168 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

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/S160053681105567X/xu5422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105567X/xu5422Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681105567X/xu5422Isup3.cml

checkCIF report

Comment top

The compound (Scheme I) was synthesized for an evaluation of its antimicrobial activity (El-Brollosy, 2008). The 1,2,4-triazine ring of is planar (r.m.s. deviation 0.019 Å); the C atom at the 6-position deviates by 0.026 (2) Å from the mean plane whereas the C atom at the 2-position deviates from the mean plane by 0.166 (4) Å in the opposite direction (Fig. 1). The amino group is hydrogen-bond donor to the exocyclic O atom at the 3-position, the hydrogen bond generating a centrosymmetric dimer (Table 1, Fig. 2).

Related literature top

For the synthesis and antimicrobial activity of the title compound, 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 C₁₄H₁₅N₃O₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Dimeric hydrogen-bonded structure.

2-{[(2-Methylprop-2-en-1-yl)oxy]methyl}-6-phenyl-2,3,4,5-tetrahydro-1,2,4- triazine-3,5-dione top

Crystal data top

C₁₄H₁₅N₃O₃	Z = 2
M_r = 273.29	F(000) = 288
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6162 (5) Å	Cell parameters from 1917 reflections
b = 11.7896 (14) Å	θ = 2.6–27.5°
c = 12.5769 (10) Å	µ = 0.10 mm⁻¹
α = 81.588 (8)°	T = 100 K
β = 85.836 (7)°	Prism, colorless
γ = 87.245 (9)°	0.30 × 0.03 × 0.03 mm
V = 674.84 (12) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3088 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1878 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.086
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.6°
ω scan	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −15→15
T_min = 0.972, T_max = 0.997	l = −16→16
9875 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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.250	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.1384P)²] where P = (F_o² + 2F_c²)/3
3088 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.53 e Å⁻³
1 restraint	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₄H₁₅N₃O₃	γ = 87.245 (9)°
M_r = 273.29	V = 674.84 (12) Å³
Triclinic, P1	Z = 2
a = 4.6162 (5) Å	Mo Kα radiation
b = 11.7896 (14) Å	µ = 0.10 mm⁻¹
c = 12.5769 (10) Å	T = 100 K
α = 81.588 (8)°	0.30 × 0.03 × 0.03 mm
β = 85.836 (7)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3088 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1878 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.997	R_int = 0.086
9875 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	1 restraint
wR(F²) = 0.250	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.53 e Å⁻³
3088 reflections	Δρ_min = −0.45 e Å⁻³
186 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.5220 (4)	0.40726 (17)	0.61847 (14)	0.0268 (5)
O2	−0.1301 (4)	0.7060 (2)	0.55343 (15)	0.0370 (6)
O3	0.0363 (4)	0.24966 (17)	0.82369 (14)	0.0261 (5)
N1	0.1946 (5)	0.5578 (2)	0.58770 (16)	0.0224 (6)
H1	0.277 (7)	0.580 (3)	0.5224 (14)	0.062 (12)*
N2	0.1685 (5)	0.4378 (2)	0.74966 (16)	0.0219 (5)
N3	−0.0574 (4)	0.5017 (2)	0.78892 (16)	0.0216 (5)
C1	0.3099 (6)	0.4641 (2)	0.6493 (2)	0.0227 (6)
C2	−0.0396 (6)	0.6266 (3)	0.6174 (2)	0.0248 (6)
C3	−0.1586 (5)	0.5929 (2)	0.73057 (19)	0.0207 (6)
C4	−0.3984 (5)	0.6607 (2)	0.7819 (2)	0.0217 (6)
C5	−0.5471 (6)	0.7527 (2)	0.7267 (2)	0.0257 (6)
H5	−0.5003	0.7749	0.6520	0.031*
C6	−0.7664 (6)	0.8135 (3)	0.7801 (2)	0.0305 (7)
H6	−0.8691	0.8762	0.7415	0.037*
C7	−0.8330 (6)	0.7822 (3)	0.8889 (2)	0.0292 (7)
H7	−0.9804	0.8239	0.9252	0.035*
C8	−0.6862 (6)	0.6905 (3)	0.9448 (2)	0.0299 (7)
H8	−0.7345	0.6689	1.0195	0.036*
C9	−0.4675 (6)	0.6294 (3)	0.8926 (2)	0.0263 (7)
H9	−0.3655	0.5668	0.9318	0.032*
C10	0.2431 (6)	0.3324 (3)	0.8212 (2)	0.0248 (6)
H10A	0.4350	0.3013	0.7963	0.030*
H10B	0.2581	0.3506	0.8950	0.030*
C11	0.0328 (6)	0.2037 (3)	0.7240 (2)	0.0266 (7)
H11A	0.2318	0.1769	0.7022	0.032*
H11B	−0.0311	0.2649	0.6670	0.032*
C12	−0.1666 (6)	0.1064 (3)	0.7350 (2)	0.0297 (7)
C13	−0.2911 (7)	0.0595 (3)	0.8283 (2)	0.0357 (8)
H13A	−0.2548	0.0879	0.8928	0.043*
H13B	−0.4166	−0.0025	0.8307	0.043*
C14	−0.2130 (7)	0.0672 (3)	0.6292 (2)	0.0375 (8)
H14A	−0.3299	−0.0013	0.6420	0.056*
H14B	−0.0245	0.0489	0.5934	0.056*
H14C	−0.3148	0.1284	0.5833	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0280 (11)	0.0367 (12)	0.0136 (9)	0.0045 (9)	0.0047 (8)	−0.0017 (8)
O2	0.0420 (12)	0.0492 (15)	0.0141 (10)	0.0119 (11)	0.0064 (8)	0.0055 (9)
O3	0.0328 (11)	0.0321 (12)	0.0121 (9)	0.0010 (9)	0.0050 (7)	−0.0025 (8)
N1	0.0264 (12)	0.0306 (14)	0.0083 (10)	−0.0017 (10)	0.0040 (9)	0.0015 (10)
N2	0.0275 (12)	0.0259 (13)	0.0108 (10)	0.0025 (10)	0.0039 (9)	−0.0007 (9)
N3	0.0249 (12)	0.0287 (13)	0.0108 (10)	0.0010 (10)	0.0027 (8)	−0.0042 (9)
C1	0.0241 (14)	0.0313 (16)	0.0126 (12)	−0.0017 (12)	0.0007 (10)	−0.0040 (11)
C2	0.0284 (14)	0.0340 (17)	0.0106 (12)	0.0002 (12)	0.0005 (10)	0.0000 (11)
C3	0.0235 (14)	0.0255 (15)	0.0122 (12)	−0.0018 (11)	0.0011 (10)	−0.0003 (10)
C4	0.0203 (13)	0.0283 (16)	0.0165 (12)	−0.0005 (11)	0.0025 (10)	−0.0058 (11)
C5	0.0323 (15)	0.0263 (15)	0.0168 (13)	−0.0006 (12)	0.0022 (11)	0.0006 (11)
C6	0.0307 (16)	0.0345 (18)	0.0260 (15)	0.0010 (14)	−0.0010 (12)	−0.0046 (13)
C7	0.0299 (15)	0.0323 (17)	0.0266 (14)	−0.0006 (13)	0.0038 (12)	−0.0107 (13)
C8	0.0314 (16)	0.0422 (19)	0.0161 (13)	0.0044 (14)	0.0045 (11)	−0.0086 (13)
C9	0.0257 (14)	0.0360 (17)	0.0155 (13)	0.0053 (13)	0.0019 (10)	−0.0024 (12)
C10	0.0289 (14)	0.0339 (17)	0.0104 (11)	0.0030 (12)	−0.0002 (10)	−0.0009 (11)
C11	0.0333 (15)	0.0326 (17)	0.0128 (12)	0.0060 (13)	0.0015 (11)	−0.0037 (12)
C12	0.0353 (16)	0.0298 (17)	0.0223 (14)	0.0072 (13)	0.0012 (12)	−0.0024 (12)
C13	0.0461 (18)	0.0342 (18)	0.0258 (15)	−0.0044 (15)	0.0058 (13)	−0.0038 (13)
C14	0.0500 (19)	0.0383 (19)	0.0240 (15)	−0.0034 (16)	0.0003 (13)	−0.0045 (14)

Geometric parameters (Å, º) top

O1—C1	1.230 (3)	C6—H6	0.9500
O2—C2	1.220 (3)	C7—C8	1.378 (4)
O3—C10	1.393 (3)	C7—H7	0.9500
O3—C11	1.438 (3)	C8—C9	1.393 (4)
N1—C1	1.362 (4)	C8—H8	0.9500
N1—C2	1.383 (4)	C9—H9	0.9500
N1—H1	0.888 (10)	C10—H10A	0.9900
N2—N3	1.362 (3)	C10—H10B	0.9900
N2—C1	1.379 (3)	C11—C12	1.490 (4)
N2—C10	1.466 (3)	C11—H11A	0.9900
N3—C3	1.297 (4)	C11—H11B	0.9900
C2—C3	1.493 (3)	C12—C13	1.325 (4)
C3—C4	1.498 (3)	C12—C14	1.503 (4)
C4—C5	1.381 (4)	C13—H13A	0.9500
C4—C9	1.405 (4)	C13—H13B	0.9500
C5—C6	1.401 (4)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C6—C7	1.380 (4)	C14—H14C	0.9800

C10—O3—C11	113.35 (19)	C7—C8—H8	119.7
C1—N1—C2	126.5 (2)	C9—C8—H8	119.7
C1—N1—H1	119 (3)	C8—C9—C4	119.7 (3)
C2—N1—H1	115 (3)	C8—C9—H9	120.1
N3—N2—C1	124.4 (2)	C4—C9—H9	120.1
N3—N2—C10	114.3 (2)	O3—C10—N2	111.8 (2)
C1—N2—C10	121.2 (2)	O3—C10—H10A	109.3
C3—N3—N2	120.6 (2)	N2—C10—H10A	109.3
O1—C1—N1	123.2 (2)	O3—C10—H10B	109.3
O1—C1—N2	122.5 (3)	N2—C10—H10B	109.3
N1—C1—N2	114.2 (2)	H10A—C10—H10B	107.9
O2—C2—N1	120.4 (2)	O3—C11—C12	111.1 (2)
O2—C2—C3	126.1 (3)	O3—C11—H11A	109.4
N1—C2—C3	113.5 (2)	C12—C11—H11A	109.4
N3—C3—C2	120.7 (2)	O3—C11—H11B	109.4
N3—C3—C4	117.0 (2)	C12—C11—H11B	109.4
C2—C3—C4	122.4 (3)	H11A—C11—H11B	108.0
C5—C4—C9	119.2 (2)	C13—C12—C11	123.4 (3)
C5—C4—C3	123.4 (2)	C13—C12—C14	123.5 (3)
C9—C4—C3	117.3 (2)	C11—C12—C14	113.1 (2)
C4—C5—C6	120.5 (2)	C12—C13—H13A	120.0
C4—C5—H5	119.8	C12—C13—H13B	120.0
C6—C5—H5	119.8	H13A—C13—H13B	120.0
C7—C6—C5	119.9 (3)	C12—C14—H14A	109.5
C7—C6—H6	120.0	C12—C14—H14B	109.5
C5—C6—H6	120.0	H14A—C14—H14B	109.5
C8—C7—C6	120.1 (3)	C12—C14—H14C	109.5
C8—C7—H7	119.9	H14A—C14—H14C	109.5
C6—C7—H7	119.9	H14B—C14—H14C	109.5
C7—C8—C9	120.5 (3)

C1—N2—N3—C3	1.5 (4)	C2—C3—C4—C5	6.4 (4)
C10—N2—N3—C3	−175.2 (2)	N3—C3—C4—C9	8.3 (4)
C2—N1—C1—O1	−178.9 (2)	C2—C3—C4—C9	−172.1 (2)
C2—N1—C1—N2	1.1 (4)	C9—C4—C5—C6	−0.6 (4)
N3—N2—C1—O1	176.5 (2)	C3—C4—C5—C6	−179.1 (2)
C10—N2—C1—O1	−7.1 (4)	C4—C5—C6—C7	0.6 (4)
N3—N2—C1—N1	−3.5 (4)	C5—C6—C7—C8	−0.6 (4)
C10—N2—C1—N1	172.9 (2)	C6—C7—C8—C9	0.7 (4)
C1—N1—C2—O2	−177.2 (2)	C7—C8—C9—C4	−0.7 (4)
C1—N1—C2—C3	2.8 (4)	C5—C4—C9—C8	0.7 (4)
N2—N3—C3—C2	3.0 (4)	C3—C4—C9—C8	179.2 (2)
N2—N3—C3—C4	−177.40 (19)	C11—O3—C10—N2	68.7 (3)
O2—C2—C3—N3	175.1 (3)	N3—N2—C10—O3	72.8 (2)
N1—C2—C3—N3	−4.9 (4)	C1—N2—C10—O3	−104.0 (3)
O2—C2—C3—C4	−4.5 (4)	C10—O3—C11—C12	173.3 (2)
N1—C2—C3—C4	175.5 (2)	O3—C11—C12—C13	−8.5 (4)
N3—C3—C4—C5	−173.3 (2)	O3—C11—C12—C14	171.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (1)	1.93 (1)	2.802 (3)	168 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃O₃
M_r	273.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	4.6162 (5), 11.7896 (14), 12.5769 (10)
α, β, γ (°)	81.588 (8), 85.836 (7), 87.245 (9)
V (Å³)	674.84 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.03 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.972, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	9875, 3088, 1878
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.250, 1.01
No. of reflections	3088
No. of parameters	186
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.45

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 (1)	1.93 (1)	2.802 (3)	168 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

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

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
El-Brollosy, N. R. (2008). Monatsh. Chem. 139, 1483–1490. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

2-{[(2-Methyl­prop-2-en-1-yl)­­oxy]meth­yl}-6-phenyl-2,3,4,5-tetra­hydro-1,2,4-triazine-3,5-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{[(2-Methylprop-2-en-1-yl)oxy]methyl}-6-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5-dione