2-[(Cyclo-hex-3-en-1-ylmeth-oxy)meth-yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione.

In the title 1,2,4-triazine derivative, C(17)H(19)N(3)O(3), the heterocyclic ring is planar (r.m.s. deviation = 0.040 Å) and effectively coplanar with the adjacent phenyl ring [dihedral angle = 4.5 (2)°] but almost perpendicular to the (cyclo-hex-3-en-1-ylmeth-oxy)methyl residue [N-N-C-O torsion angle = 71.6 (5)°], so that the mol-ecule has an 'L' shape. Supra-molecular chains along [001] are formed in the crystal via N-H⋯O hydrogen bonds where the acceptor O atom is the ether O atom. The adjacent carbonyl O atom forms a complementary C-H⋯O contact resulting in the formation of a seven-membered {⋯HNCO⋯HCO} heterosynthon; the second carbonyl O atom forms an intra-molecular C-H⋯O contact. Chains are connected into a supra-molecular layer in the ac plane by π-π inter-actions [ring centroid-centroid distance = 3.488 (3) Å]. The central atom in the -CH(2)CH(2)C(H)= residue of the cyclo-hexene ring is disordered over two sites, with the major component having a site-occupancy factor of 0.51 (2).

Related literature

For the potential medicinal applications of 1,2,4-triazines, see: Ban et al. (2010 ▶); Irannejad et al. (2010 ▶); Sangshetti & Shinde (2010 ▶). For the synthesis, see: El-Brollosy (2008 ▶).

Experimental

Crystal data

C17H19N3O3

M = 313.35

Monoclinic,

a = 4.7924 (6) Å

b = 13.7083 (19) Å

c = 11.8293 (15) Å

β = 101.538 (12)°

V = 761.43 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.15 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.806, T max = 1.000

4230 measured reflections

1757 independent reflections

1158 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.133

S = 1.04

1757 reflections

212 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021198/su2425sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021198/su2425Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021198/su2425Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H19N3O3	F(000) = 332
Mr = 313.35	Dx = 1.367 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 801 reflections
a = 4.7924 (6) Å	θ = 2.3–27.5°
b = 13.7083 (19) Å	µ = 0.10 mm−1
c = 11.8293 (15) Å	T = 100 K
β = 101.538 (12)°	Plate, colourless
V = 761.43 (17) Å3	0.35 × 0.15 × 0.03 mm
Z = 2

Agilent SuperNova Dual diffractometer with an Atlas detector	1757 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1158 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.078
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scan	h = −5→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −17→17
Tmin = 0.806, Tmax = 1.000	l = −15→15
4230 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0421P)2] where P = (Fo2 + 2Fc2)/3
1757 reflections	(Δ/σ)max = 0.002
212 parameters	Δρmax = 0.24 e Å−3
4 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4970 (7)	0.7062 (3)	0.4998 (3)	0.0321 (9)
O2	1.2011 (7)	0.4812 (3)	0.5519 (3)	0.0245 (8)
O3	0.9583 (7)	0.3645 (2)	0.8023 (3)	0.0228 (8)
N1	0.8476 (9)	0.5948 (3)	0.5278 (4)	0.0205 (9)
H1	0.8696	0.6052	0.4567	0.025*
N2	0.9682 (7)	0.5123 (3)	0.7000 (3)	0.0190 (10)
N3	0.7856 (7)	0.5669 (3)	0.7480 (3)	0.0194 (9)
C1	0.4436 (9)	0.6924 (4)	0.7489 (4)	0.0201 (11)
C2	0.2789 (10)	0.7697 (4)	0.6974 (5)	0.0253 (12)
H2	0.2844	0.7872	0.6202	0.030*
C3	0.1041 (10)	0.8224 (4)	0.7579 (5)	0.0275 (13)
H3	−0.0072	0.8754	0.7221	0.033*
C4	0.0957 (11)	0.7960 (4)	0.8709 (5)	0.0244 (12)
H4	−0.0211	0.8315	0.9125	0.029*
C5	0.2553 (10)	0.7192 (4)	0.9223 (5)	0.0260 (12)
H5	0.2458	0.7011	0.9989	0.031*
C6	0.4310 (11)	0.6673 (4)	0.8634 (5)	0.0251 (12)
H6	0.5428	0.6148	0.9004	0.030*
C7	0.6321 (9)	0.6348 (4)	0.6886 (4)	0.0205 (11)
C8	0.6423 (10)	0.6503 (4)	0.5652 (4)	0.0209 (11)
C9	1.0207 (10)	0.5252 (4)	0.5896 (4)	0.0185 (11)
C10	1.1326 (10)	0.4421 (4)	0.7787 (4)	0.0217 (11)
H10A	1.2888	0.4159	0.7441	0.026*
H10B	1.2188	0.4752	0.8517	0.026*
C11	0.8986 (11)	0.2912 (4)	0.7141 (5)	0.0252 (12)
H11A	1.0778	0.2701	0.6920	0.030*
H11B	0.7715	0.3182	0.6449	0.030*
C12	0.7570 (10)	0.2050 (4)	0.7590 (4)	0.0221 (11)
H12	0.5764	0.2283	0.7801	0.027*
C13	0.6801 (13)	0.1266 (4)	0.6644 (5)	0.0376 (14)
H13A	0.5451	0.1545	0.5980	0.045*
H13B	0.8544	0.1070	0.6373	0.045*
C14	0.5488 (12)	0.0383 (4)	0.7073 (6)	0.0365 (14)
H14	0.4158	−0.0003	0.6557	0.044*
C15	0.6234 (12)	0.0133 (4)	0.8234 (6)	0.0360 (14)
H15	0.5694	−0.0490	0.8468	0.043*
C16	0.779 (5)	0.0777 (12)	0.9093 (9)	0.032 (5)	0.51 (2)
H16A	0.9165	0.0382	0.9644	0.039*	0.51 (2)
H16B	0.6429	0.1066	0.9529	0.039*	0.51 (2)
C16'	0.837 (5)	0.0637 (12)	0.9049 (10)	0.032 (5)	0.49
H16C	1.0033	0.0199	0.9266	0.039*	0.49 (2)
H16D	0.7602	0.0758	0.9753	0.039*	0.49 (2)
C17	0.9405 (10)	0.1602 (4)	0.8654 (5)	0.0253 (12)
H17A	1.1188	0.1347	0.8463	0.030*
H17B	0.9912	0.2105	0.9261	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.032 (2)	0.039 (2)	0.026 (2)	0.0098 (18)	0.0082 (17)	0.0077 (19)
O2	0.0274 (18)	0.027 (2)	0.0197 (19)	0.0025 (16)	0.0073 (16)	−0.0009 (16)
O3	0.032 (2)	0.0200 (19)	0.0175 (18)	−0.0002 (16)	0.0074 (16)	−0.0005 (15)
N1	0.028 (2)	0.021 (2)	0.014 (2)	0.0002 (18)	0.0081 (18)	0.0006 (17)
N2	0.024 (2)	0.018 (2)	0.015 (2)	0.0027 (18)	0.0042 (19)	−0.0017 (19)
N3	0.016 (2)	0.022 (2)	0.021 (2)	−0.0021 (18)	0.0038 (18)	−0.0020 (19)
C1	0.017 (2)	0.020 (3)	0.023 (3)	−0.006 (2)	0.004 (2)	−0.002 (2)
C2	0.029 (3)	0.024 (3)	0.023 (3)	−0.007 (2)	0.005 (2)	−0.002 (2)
C3	0.022 (3)	0.023 (3)	0.037 (3)	0.002 (2)	0.005 (3)	−0.002 (3)
C4	0.027 (3)	0.022 (3)	0.026 (3)	−0.003 (2)	0.011 (2)	−0.008 (2)
C5	0.025 (3)	0.029 (3)	0.025 (3)	−0.006 (2)	0.008 (2)	−0.002 (2)
C6	0.024 (3)	0.026 (3)	0.026 (3)	−0.005 (2)	0.006 (2)	−0.001 (3)
C7	0.017 (3)	0.021 (3)	0.023 (3)	−0.004 (2)	0.004 (2)	0.001 (2)
C8	0.025 (3)	0.021 (3)	0.017 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
C9	0.022 (3)	0.020 (3)	0.014 (3)	−0.005 (2)	0.004 (2)	0.000 (2)
C10	0.024 (3)	0.021 (3)	0.021 (3)	−0.005 (2)	0.005 (2)	0.002 (2)
C11	0.035 (3)	0.022 (3)	0.019 (2)	−0.001 (2)	0.005 (2)	−0.003 (2)
C12	0.021 (2)	0.021 (3)	0.024 (3)	0.003 (2)	0.004 (2)	0.001 (2)
C13	0.047 (3)	0.027 (3)	0.033 (3)	−0.004 (3)	−0.006 (3)	−0.004 (3)
C14	0.034 (3)	0.030 (3)	0.048 (4)	−0.011 (3)	0.012 (3)	−0.011 (3)
C15	0.033 (3)	0.021 (3)	0.053 (4)	−0.003 (3)	0.007 (3)	0.004 (3)
C16	0.014 (8)	0.029 (6)	0.055 (5)	0.013 (6)	0.008 (4)	0.012 (4)
C16'	0.014 (8)	0.029 (6)	0.055 (5)	0.013 (6)	0.008 (4)	0.012 (4)
C17	0.028 (3)	0.022 (3)	0.025 (3)	−0.002 (2)	0.002 (2)	0.005 (2)

O1—C8	1.207 (6)	C10—H10A	0.9900
O2—C9	1.210 (5)	C10—H10B	0.9900
O3—C10	1.415 (6)	C11—C12	1.510 (7)
O3—C11	1.435 (6)	C11—H11A	0.9900
N1—C9	1.375 (6)	C11—H11B	0.9900
N1—C8	1.385 (6)	C12—C17	1.514 (7)
N1—H1	0.8800	C12—C13	1.543 (8)
N2—N3	1.359 (5)	C12—H12	1.0000
N2—C9	1.390 (5)	C13—C14	1.499 (8)
N2—C10	1.456 (6)	C13—H13A	0.9900
N3—C7	1.301 (6)	C13—H13B	0.9900
C1—C2	1.387 (7)	C14—C15	1.390 (9)
C1—C6	1.410 (7)	C14—H14	0.9500
C1—C7	1.486 (6)	C15—C16'	1.435 (11)
C2—C3	1.406 (7)	C15—C16	1.437 (11)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.392 (7)	C16—C17	1.521 (9)
C3—H3	0.9500	C16—H16A	0.9900
C4—C5	1.371 (7)	C16—H16B	0.9900
C4—H4	0.9500	C16'—C17	1.519 (10)
C5—C6	1.391 (7)	C16'—H16C	0.9900
C5—H5	0.9500	C16'—H16D	0.9900
C6—H6	0.9500	C17—H17A	0.9900
C7—C8	1.486 (6)	C17—H17B	0.9900
C10—O3—C11	115.1 (3)	O3—C11—H11B	109.8
C9—N1—C8	127.1 (4)	C12—C11—H11B	109.8
C9—N1—H1	116.4	H11A—C11—H11B	108.3
C8—N1—H1	116.4	C11—C12—C17	112.5 (4)
N3—N2—C9	125.1 (4)	C11—C12—C13	110.4 (4)
N3—N2—C10	114.1 (4)	C17—C12—C13	109.5 (4)
C9—N2—C10	120.6 (4)	C11—C12—H12	108.1
C7—N3—N2	120.7 (4)	C17—C12—H12	108.1
C2—C1—C6	118.6 (5)	C13—C12—H12	108.1
C2—C1—C7	122.8 (4)	C14—C13—C12	111.9 (5)
C6—C1—C7	118.6 (4)	C14—C13—H13A	109.2
C1—C2—C3	120.9 (5)	C12—C13—H13A	109.2
C1—C2—H2	119.6	C14—C13—H13B	109.2
C3—C2—H2	119.6	C12—C13—H13B	109.2
C4—C3—C2	119.3 (5)	H13A—C13—H13B	107.9
C4—C3—H3	120.3	C15—C14—C13	119.4 (5)
C2—C3—H3	120.3	C15—C14—H14	120.3
C5—C4—C3	120.3 (5)	C13—C14—H14	120.3
C5—C4—H4	119.9	C14—C15—C16'	123.6 (6)
C3—C4—H4	119.9	C14—C15—C16	122.8 (6)
C4—C5—C6	120.7 (5)	C14—C15—H15	118.6
C4—C5—H5	119.6	C16'—C15—H15	115.8
C6—C5—H5	119.6	C16—C15—H15	118.6
C5—C6—C1	120.2 (5)	C15—C16—C17	116.2 (8)
C5—C6—H6	119.9	C15—C16—H16A	108.2
C1—C6—H6	119.9	C17—C16—H16A	108.2
N3—C7—C1	117.0 (4)	C15—C16—H16B	108.2
N3—C7—C8	120.4 (4)	C17—C16—H16B	108.2
C1—C7—C8	122.6 (4)	H16A—C16—H16B	107.4
O1—C8—N1	120.0 (4)	C15—C16'—C17	116.5 (8)
O1—C8—C7	126.4 (5)	C15—C16'—H16C	108.2
N1—C8—C7	113.6 (4)	C17—C16'—H16C	108.2
O2—C9—N1	123.3 (4)	C15—C16'—H16D	108.2
O2—C9—N2	124.0 (4)	C17—C16'—H16D	108.2
N1—C9—N2	112.6 (4)	H16C—C16'—H16D	107.3
O3—C10—N2	111.0 (4)	C16'—C17—C12	116.0 (7)
O3—C10—H10A	109.4	C16—C17—C12	109.6 (8)
N2—C10—H10A	109.4	C16'—C17—H17A	96.5
O3—C10—H10B	109.4	C16—C17—H17A	109.8
N2—C10—H10B	109.4	C12—C17—H17A	109.7
H10A—C10—H10B	108.0	C16'—C17—H17B	115.5
O3—C11—C12	109.3 (4)	C16—C17—H17B	109.7
O3—C11—H11A	109.8	C12—C17—H17B	109.7
C12—C11—H11A	109.8	H17A—C17—H17B	108.2
C9—N2—N3—C7	3.3 (6)	N3—N2—C9—N1	−5.5 (6)
C10—N2—N3—C7	177.7 (4)	C10—N2—C9—N1	−179.5 (4)
C6—C1—C2—C3	0.4 (7)	C11—O3—C10—N2	79.3 (5)
C7—C1—C2—C3	−179.8 (5)	N3—N2—C10—O3	71.6 (5)
C1—C2—C3—C4	−0.4 (7)	C9—N2—C10—O3	−113.8 (4)
C2—C3—C4—C5	−0.3 (8)	C10—O3—C11—C12	170.0 (4)
C3—C4—C5—C6	1.0 (8)	O3—C11—C12—C17	−59.4 (5)
C4—C5—C6—C1	−1.0 (7)	O3—C11—C12—C13	177.9 (4)
C2—C1—C6—C5	0.3 (7)	C11—C12—C13—C14	177.9 (5)
C7—C1—C6—C5	−179.5 (4)	C17—C12—C13—C14	53.4 (6)
N2—N3—C7—C1	−178.5 (4)	C12—C13—C14—C15	−29.4 (7)
N2—N3—C7—C8	3.3 (7)	C13—C14—C15—C16'	−4.5 (16)
C2—C1—C7—N3	177.0 (5)	C13—C14—C15—C16	12.3 (16)
C6—C1—C7—N3	−3.2 (6)	C14—C15—C16—C17	−19 (3)
C2—C1—C7—C8	−4.9 (7)	C16'—C15—C16—C17	79 (3)
C6—C1—C7—C8	174.9 (4)	C14—C15—C16'—C17	12 (3)
C9—N1—C8—O1	−177.0 (5)	C16—C15—C16'—C17	−79 (3)
C9—N1—C8—C7	4.6 (7)	C15—C16'—C17—C16	79 (3)
N3—C7—C8—O1	174.8 (5)	C15—C16'—C17—C12	15 (2)
C1—C7—C8—O1	−3.2 (8)	C15—C16—C17—C16'	−78 (3)
N3—C7—C8—N1	−6.9 (6)	C15—C16—C17—C12	43 (2)
C1—C7—C8—N1	175.1 (4)	C11—C12—C17—C16'	−170.4 (12)
C8—N1—C9—O2	−178.0 (5)	C13—C12—C17—C16'	−47.1 (12)
C8—N1—C9—N2	1.1 (7)	C11—C12—C17—C16	177.0 (10)
N3—N2—C9—O2	173.6 (4)	C13—C12—C17—C16	−59.8 (11)
C10—N2—C9—O2	−0.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.88	2.00	2.877 (5)	174
C2—H2···O1	0.95	2.21	2.880 (7)	127
C10—H10B···O2ii	0.99	2.46	3.352 (6)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.88	2.00	2.877 (5)	174
C2—H2⋯O1	0.95	2.21	2.880 (7)	127
C10—H10B⋯O2ii	0.99	2.46	3.352 (6)	150

Symmetry codes: (i) ; (ii) .