(3,6-Dimethyl-1,2,4,5-tetra-zine-1,4-di-yl)bis-[(morpholin-4-yl)methanone].

In the title mol-ecule, C(14)H(22)N(6)O(4), the amide-substituted N atoms of the tetra-zine ring deviate from the approximate plane of the four other atoms in the ring by 0.160 (2) and 0.243 (2) Å, forming a slight boat conformation. The morpholine rings are in chair conformations.

Related literature

For chemical reactions of 1,2,4,5-tetra­zine derivatives, see: Domingo et al. (2009 ▶); Lorincz et al. (2010 ▶). For their bio­logical activities, see: Devaraj et al. (2009 ▶); Eremeev et al. (1978 ▶, 1980 ▶); Han et al. (2010 ▶); Neunhoeffer (1984 ▶); Sauer (1996 ▶). For anti-n class="Disease">tumor activity of 1,2,4,5-tetra­zine derivatives, see: Hu et al. (2002 ▶, 2004 ▶); Rao & Hu, (2005 ▶, 2006 ▶). For details of the synthesis, see: Hu et al. (2004 ▶); Skorianetz & Kováts (1970 ▶, 1971 ▶); Sun et al. (2003 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H22N6O4

M = 338.38

Monoclinic,

a = 15.285 (3) Å

b = 6.5977 (14) Å

c = 16.729 (4) Å

β = 106.576 (3)°

V = 1617.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.55 × 0.42 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.944, T max = 0.971

9248 measured reflections

3714 independent reflections

2908 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.03

3714 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004849/lh5412sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812004849/lh5412Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004849/lh5412Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812004849/lh5412Isup4.cml

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

C14H22N6O4	F(000) = 720
Mr = 338.38	Dx = 1.390 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6920 reflections
a = 15.285 (3) Å	θ = 2.9–28.2°
b = 6.5977 (14) Å	µ = 0.10 mm−1
c = 16.729 (4) Å	T = 298 K
β = 106.576 (3)°	Block, yellow
V = 1617.0 (6) Å3	0.55 × 0.42 × 0.28 mm
Z = 4

Bruker SMART CCD diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	2908 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→20
Tmin = 0.944, Tmax = 0.971	k = −8→8
9248 measured reflections	l = −18→21

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0823P)2 + 0.2523P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3714 reflections	Δρmax = 0.27 e Å−3
220 parameters	Δρmin = −0.27 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: 0.036 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N2	0.68618 (8)	0.70860 (18)	0.11259 (7)	0.0374 (3)
N4	0.59388 (8)	0.60296 (19)	0.19430 (7)	0.0409 (3)
N5	0.55633 (9)	0.43942 (18)	0.13981 (8)	0.0450 (3)
N1	0.66936 (9)	0.51243 (19)	0.07644 (8)	0.0456 (3)
O4	0.49306 (9)	0.2853 (2)	0.41742 (7)	0.0586 (3)
O3	0.74085 (9)	0.7091 (2)	−0.18200 (7)	0.0620 (4)
N6	0.53166 (9)	0.5633 (2)	0.30490 (8)	0.0444 (3)
C6	0.59824 (9)	0.3973 (2)	0.08605 (8)	0.0359 (3)
N3	0.75197 (8)	0.57709 (19)	−0.01932 (7)	0.0416 (3)
O1	0.75909 (9)	0.27148 (18)	0.04345 (9)	0.0643 (4)
C3	0.64652 (9)	0.7449 (2)	0.16842 (8)	0.0333 (3)
O2	0.48046 (10)	0.8161 (2)	0.21322 (9)	0.0764 (5)
C4	0.72971 (10)	0.4435 (2)	0.03193 (8)	0.0397 (3)
C5	0.52962 (10)	0.6716 (2)	0.23773 (9)	0.0415 (3)
C11	0.59485 (10)	0.3983 (2)	0.33971 (10)	0.0461 (4)
H11A	0.6405	0.4442	0.3895	0.055*
H11B	0.6258	0.3549	0.2994	0.055*
C12	0.54193 (11)	0.2249 (3)	0.36082 (10)	0.0492 (4)
H12A	0.4994	0.1738	0.3101	0.059*
H12B	0.5836	0.1161	0.3854	0.059*
C7	0.82145 (11)	0.5206 (3)	−0.06011 (10)	0.0490 (4)
H7A	0.8456	0.3874	−0.0413	0.059*
H7B	0.8714	0.6170	−0.0455	0.059*
C10	0.70416 (11)	0.7647 (2)	−0.05175 (9)	0.0461 (4)
H10A	0.7453	0.8788	−0.0350	0.055*
H10B	0.6533	0.7839	−0.0287	0.055*
C14	0.47410 (12)	0.6227 (3)	0.35760 (11)	0.0531 (4)
H14A	0.4279	0.7179	0.3278	0.064*
H14B	0.5111	0.6889	0.4076	0.064*
C1	0.66582 (12)	0.9416 (3)	0.21394 (11)	0.0535 (4)
H1A	0.6875	0.9164	0.2728	0.080*
H1B	0.6109	1.0208	0.2020	0.080*
H1C	0.7115	1.0143	0.1963	0.080*
C13	0.42906 (12)	0.4385 (3)	0.38095 (11)	0.0548 (4)
H13A	0.3958	0.4774	0.4200	0.066*
H13B	0.3854	0.3847	0.3315	0.066*
C2	0.56523 (12)	0.2236 (3)	0.02845 (12)	0.0594 (5)
H2A	0.5571	0.2667	−0.0280	0.089*
H2B	0.5081	0.1761	0.0345	0.089*
H2C	0.6093	0.1159	0.0418	0.089*
C9	0.66960 (12)	0.7561 (3)	−0.14556 (10)	0.0588 (5)
H9A	0.6222	0.6540	−0.1618	0.071*
H9B	0.6429	0.8858	−0.1666	0.071*
C8	0.77950 (13)	0.5188 (3)	−0.15316 (10)	0.0581 (5)
H8A	0.8259	0.4854	−0.1803	0.070*
H8B	0.7326	0.4153	−0.1678	0.070*

	U11	U22	U33	U12	U13	U23
N2	0.0443 (6)	0.0343 (6)	0.0378 (6)	−0.0095 (5)	0.0183 (5)	−0.0074 (5)
N4	0.0480 (7)	0.0397 (7)	0.0428 (6)	−0.0052 (5)	0.0255 (5)	−0.0037 (5)
N5	0.0469 (7)	0.0330 (6)	0.0625 (8)	−0.0085 (5)	0.0278 (6)	−0.0075 (5)
N1	0.0601 (8)	0.0379 (7)	0.0506 (7)	−0.0152 (6)	0.0346 (6)	−0.0145 (5)
O4	0.0659 (7)	0.0694 (8)	0.0489 (6)	0.0032 (6)	0.0302 (6)	0.0145 (6)
O3	0.0741 (8)	0.0787 (9)	0.0390 (6)	0.0023 (7)	0.0255 (6)	0.0062 (6)
N6	0.0515 (7)	0.0449 (7)	0.0471 (7)	0.0098 (6)	0.0306 (6)	0.0054 (5)
C6	0.0375 (7)	0.0288 (7)	0.0417 (7)	−0.0002 (5)	0.0119 (6)	−0.0014 (5)
N3	0.0471 (7)	0.0461 (7)	0.0390 (6)	0.0091 (5)	0.0239 (5)	0.0036 (5)
O1	0.0768 (8)	0.0459 (7)	0.0819 (9)	0.0174 (6)	0.0417 (7)	0.0147 (6)
C3	0.0353 (6)	0.0348 (7)	0.0297 (6)	−0.0013 (5)	0.0089 (5)	−0.0013 (5)
O2	0.0777 (9)	0.0787 (9)	0.0906 (10)	0.0378 (8)	0.0525 (8)	0.0386 (8)
C4	0.0438 (7)	0.0405 (8)	0.0376 (7)	0.0007 (6)	0.0163 (6)	−0.0037 (6)
C5	0.0431 (7)	0.0416 (8)	0.0456 (8)	0.0033 (6)	0.0221 (6)	0.0017 (6)
C11	0.0434 (8)	0.0514 (9)	0.0468 (8)	0.0064 (7)	0.0182 (6)	0.0062 (7)
C12	0.0541 (9)	0.0496 (9)	0.0457 (8)	0.0062 (7)	0.0173 (7)	0.0079 (7)
C7	0.0487 (8)	0.0588 (10)	0.0483 (8)	0.0086 (7)	0.0278 (7)	0.0008 (7)
C10	0.0564 (9)	0.0445 (8)	0.0424 (8)	0.0095 (7)	0.0223 (7)	0.0053 (6)
C14	0.0653 (10)	0.0531 (10)	0.0544 (9)	0.0064 (8)	0.0386 (8)	−0.0022 (7)
C1	0.0623 (10)	0.0481 (9)	0.0552 (9)	−0.0113 (8)	0.0248 (8)	−0.0196 (7)
C13	0.0541 (9)	0.0674 (11)	0.0531 (9)	0.0012 (8)	0.0316 (8)	0.0028 (8)
C2	0.0529 (9)	0.0473 (9)	0.0776 (12)	−0.0106 (7)	0.0179 (9)	−0.0261 (8)
C9	0.0598 (10)	0.0707 (12)	0.0452 (9)	0.0083 (9)	0.0138 (8)	0.0096 (8)
C8	0.0704 (11)	0.0663 (11)	0.0470 (9)	−0.0035 (9)	0.0318 (8)	−0.0119 (8)

N2—C3	1.2730 (17)	C11—H11B	0.9700
N2—N1	1.4207 (16)	C12—H12A	0.9700
N4—C3	1.3821 (17)	C12—H12B	0.9700
N4—N5	1.4235 (17)	C7—C8	1.505 (2)
N4—C5	1.4509 (17)	C7—H7A	0.9700
N5—C6	1.2748 (18)	C7—H7B	0.9700
N1—C6	1.3728 (17)	C10—C9	1.507 (2)
N1—C4	1.4155 (17)	C10—H10A	0.9700
O4—C13	1.418 (2)	C10—H10B	0.9700
O4—C12	1.4201 (19)	C14—C13	1.502 (2)
O3—C8	1.413 (2)	C14—H14A	0.9700
O3—C9	1.426 (2)	C14—H14B	0.9700
N6—C5	1.3245 (19)	C1—H1A	0.9600
N6—C11	1.4620 (19)	C1—H1B	0.9600
N6—C14	1.4653 (17)	C1—H1C	0.9600
C6—C2	1.490 (2)	C13—H13A	0.9700
N3—C4	1.3392 (18)	C13—H13B	0.9700
N3—C10	1.4609 (19)	C2—H2A	0.9600
N3—C7	1.4650 (17)	C2—H2B	0.9600
O1—C4	1.2158 (18)	C2—H2C	0.9600
C3—C1	1.4911 (19)	C9—H9A	0.9700
O2—C5	1.2104 (19)	C9—H9B	0.9700
C11—C12	1.500 (2)	C8—H8A	0.9700
C11—H11A	0.9700	C8—H8B	0.9700
C3—N2—N1	114.67 (11)	C8—C7—H7B	109.8
C3—N4—N5	118.51 (11)	H7A—C7—H7B	108.2
C3—N4—C5	118.88 (12)	N3—C10—C9	110.14 (13)
N5—N4—C5	110.52 (11)	N3—C10—H10A	109.6
C6—N5—N4	115.15 (11)	C9—C10—H10A	109.6
C6—N1—C4	122.73 (12)	N3—C10—H10B	109.6
C6—N1—N2	120.49 (11)	C9—C10—H10B	109.6
C4—N1—N2	116.78 (11)	H10A—C10—H10B	108.1
C13—O4—C12	110.04 (12)	N6—C14—C13	109.79 (13)
C8—O3—C9	110.07 (13)	N6—C14—H14A	109.7
C5—N6—C11	126.36 (12)	C13—C14—H14A	109.7
C5—N6—C14	119.56 (13)	N6—C14—H14B	109.7
C11—N6—C14	113.66 (12)	C13—C14—H14B	109.7
N5—C6—N1	122.43 (12)	H14A—C14—H14B	108.2
N5—C6—C2	118.58 (13)	C3—C1—H1A	109.5
N1—C6—C2	118.90 (13)	C3—C1—H1B	109.5
C4—N3—C10	127.14 (12)	H1A—C1—H1B	109.5
C4—N3—C7	118.76 (13)	C3—C1—H1C	109.5
C10—N3—C7	113.26 (12)	H1A—C1—H1C	109.5
N2—C3—N4	122.96 (12)	H1B—C1—H1C	109.5
N2—C3—C1	118.17 (12)	O4—C13—C14	112.17 (14)
N4—C3—C1	118.54 (12)	O4—C13—H13A	109.2
O1—C4—N3	124.47 (13)	C14—C13—H13A	109.2
O1—C4—N1	118.89 (13)	O4—C13—H13B	109.2
N3—C4—N1	116.62 (13)	C14—C13—H13B	109.2
O2—C5—N6	125.04 (13)	H13A—C13—H13B	107.9
O2—C5—N4	121.32 (13)	C6—C2—H2A	109.5
N6—C5—N4	113.63 (12)	C6—C2—H2B	109.5
N6—C11—C12	108.81 (12)	H2A—C2—H2B	109.5
N6—C11—H11A	109.9	C6—C2—H2C	109.5
C12—C11—H11A	109.9	H2A—C2—H2C	109.5
N6—C11—H11B	109.9	H2B—C2—H2C	109.5
C12—C11—H11B	109.9	O3—C9—C10	111.70 (14)
H11A—C11—H11B	108.3	O3—C9—H9A	109.3
O4—C12—C11	111.39 (14)	C10—C9—H9A	109.3
O4—C12—H12A	109.4	O3—C9—H9B	109.3
C11—C12—H12A	109.4	C10—C9—H9B	109.3
O4—C12—H12B	109.4	H9A—C9—H9B	107.9
C11—C12—H12B	109.4	O3—C8—C7	111.07 (14)
H12A—C12—H12B	108.0	O3—C8—H8A	109.4
N3—C7—C8	109.40 (13)	C7—C8—H8A	109.4
N3—C7—H7A	109.8	O3—C8—H8B	109.4
C8—C7—H7A	109.8	C7—C8—H8B	109.4
N3—C7—H7B	109.8	H8A—C8—H8B	108.0
C3—N4—N5—C6	23.26 (19)	C11—N6—C5—O2	−174.99 (17)
C5—N4—N5—C6	165.46 (12)	C14—N6—C5—O2	−2.9 (3)
C3—N2—N1—C6	16.02 (19)	C11—N6—C5—N4	4.4 (2)
C3—N2—N1—C4	−163.17 (13)	C14—N6—C5—N4	176.51 (13)
N4—N5—C6—N1	−5.6 (2)	C3—N4—C5—O2	44.9 (2)
N4—N5—C6—C2	177.96 (14)	N5—N4—C5—O2	−97.15 (18)
C4—N1—C6—N5	164.79 (14)	C3—N4—C5—N6	−134.55 (14)
N2—N1—C6—N5	−14.4 (2)	N5—N4—C5—N6	83.42 (15)
C4—N1—C6—C2	−18.8 (2)	C5—N6—C11—C12	−134.69 (16)
N2—N1—C6—C2	162.09 (14)	C14—N6—C11—C12	52.82 (18)
N1—N2—C3—N4	2.27 (19)	C13—O4—C12—C11	61.50 (17)
N1—N2—C3—C1	175.66 (13)	N6—C11—C12—O4	−57.44 (17)
N5—N4—C3—N2	−22.2 (2)	C4—N3—C7—C8	117.84 (16)
C5—N4—C3—N2	−161.22 (13)	C10—N3—C7—C8	−52.37 (18)
N5—N4—C3—C1	164.45 (13)	C4—N3—C10—C9	−118.42 (16)
C5—N4—C3—C1	25.42 (19)	C7—N3—C10—C9	50.80 (18)
C10—N3—C4—O1	163.86 (16)	C5—N6—C14—C13	135.96 (16)
C7—N3—C4—O1	−4.8 (2)	C11—N6—C14—C13	−50.99 (19)
C10—N3—C4—N1	−17.6 (2)	C12—O4—C13—C14	−59.39 (18)
C7—N3—C4—N1	173.67 (13)	N6—C14—C13—O4	53.49 (19)
C6—N1—C4—O1	−44.3 (2)	C8—O3—C9—C10	59.94 (19)
N2—N1—C4—O1	134.89 (16)	N3—C10—C9—O3	−53.83 (19)
C6—N1—C4—N3	137.12 (15)	C9—O3—C8—C7	−61.71 (18)
N2—N1—C4—N3	−43.71 (18)	N3—C7—C8—O3	57.37 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2	0.97	2.37	2.758 (2)	103
C1—H1B···O2	0.96	2.46	2.949 (2)	111
C2—H2C···O1	0.96	2.50	2.919 (2)	106
C7—H7A···O1	0.97	2.33	2.748 (2)	105
C10—H10B···N1	0.97	2.47	2.881 (2)	105
C10—H10B···N2	0.97	2.33	2.8640 (19)	114
C11—H11B···N4	0.97	2.35	2.7787 (19)	106