3,6-Dimethyl-N,N-bis-(1-phenyl-eth-yl)-1,4-dihydro-1,2,4,5-tetra-zine-1,4-dicarboxamide.

In the title mol-ecule, C(22)H(26)N(6)O(2), the central tetra-zine ring exhibits a boat conformation, and the two phenyl rings form a dihedral angle of 88.39 (6)°. In the crystal, weak N-H⋯O and C-H⋯O hydrogen bonds link mol-ecules into layers parallel to the ab plane.

Related literature

For structure–activity relationships in 1,2,4,5-tetra­zine derivatives, see: Hu et al. (2002 ▶, 2004 ▶); Rao & Hu (2005 ▶, 2006 ▶). For standard bond lengths in organic compounds, see: Allen et al. (1987 ▶). For details of the synthesis, see: Hu et al. (2004 ▶); Skorianetz & Kovats (1970 ▶, 1971 ▶); Sun et al. (2003 ▶).

Experimental

Crystal data

C22H26N6O2

M = 406.49

Monoclinic,

a = 10.4653 (15) Å

b = 8.0606 (12) Å

c = 13.711 (2) Å

β = 108.702 (1)°

V = 1095.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.37 × 0.31 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.970, T max = 0.979

8343 measured reflections

4014 independent reflections

3809 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.06

4014 reflections

276 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.09 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S160053681200133X/cv5230sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200133X/cv5230Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200133X/cv5230Isup3.cdx

Supplementary material file. DOI: 10.1107/S160053681200133X/cv5230Isup4.cml

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

C22H26N6O2	F(000) = 432
Mr = 406.49	Dx = 1.232 Mg m−3
Monoclinic, P21	Melting point = 414–416 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 10.4653 (15) Å	Cell parameters from 5504 reflections
b = 8.0606 (12) Å	θ = 3.0–28.2°
c = 13.711 (2) Å	µ = 0.08 mm−1
β = 108.702 (1)°	T = 298 K
V = 1095.5 (3) Å3	Block, colourless
Z = 2	0.37 × 0.31 × 0.26 mm

Bruker SMART CCD area-detector diffractometer	4014 independent reflections
Radiation source: fine-focus sealed tube	3809 reflections with I > 2σ(I)
graphite	Rint = 0.016
phi and ω scans	θmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.970, Tmax = 0.979	k = −9→9
8343 measured reflections	l = −16→16

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.1082P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4014 reflections	Δρmax = 0.12 e Å−3
276 parameters	Δρmin = −0.09 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.079 (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
C6	0.61215 (13)	0.43115 (19)	0.45138 (10)	0.0457 (3)
C2	0.46716 (15)	0.3828 (3)	0.42427 (14)	0.0711 (5)
H2A	0.4590	0.2892	0.4652	0.107*
H2B	0.4330	0.3540	0.3526	0.107*
H2C	0.4163	0.4742	0.4376	0.107*
C3	0.87224 (13)	0.45508 (17)	0.46277 (10)	0.0426 (3)
C4	1.00874 (16)	0.4220 (3)	0.45547 (13)	0.0663 (5)
H4A	1.0746	0.4853	0.5069	0.099*
H4B	1.0107	0.4533	0.3884	0.099*
H4C	1.0290	0.3059	0.4664	0.099*
C5	0.57571 (13)	0.67504 (18)	0.33409 (9)	0.0415 (3)
C1	0.57492 (15)	0.9210 (2)	0.23003 (11)	0.0541 (4)
H1	0.4798	0.9198	0.2263	0.065*
C7	0.6404 (2)	1.0771 (3)	0.28855 (15)	0.0829 (6)
H7A	0.7352	1.0766	0.2974	0.124*
H7B	0.6274	1.0790	0.3548	0.124*
H7C	0.5995	1.1737	0.2501	0.124*
C8	0.58090 (13)	0.92220 (18)	0.12079 (10)	0.0443 (3)
C9	0.46735 (16)	0.9574 (3)	0.03815 (13)	0.0680 (5)
H9	0.3853	0.9760	0.0492	0.082*
C10	0.47455 (17)	0.9652 (3)	−0.06069 (14)	0.0762 (6)
H10	0.3974	0.9893	−0.1155	0.091*
C11	0.59346 (17)	0.9381 (3)	−0.07856 (12)	0.0671 (5)
H11	0.5977	0.9432	−0.1452	0.080*
C12	0.70692 (17)	0.9031 (3)	0.00266 (13)	0.0667 (5)
H12	0.7885	0.8839	−0.0089	0.080*
C13	0.70020 (14)	0.8965 (2)	0.10129 (11)	0.0565 (4)
H13	0.7781	0.8741	0.1558	0.068*
C14	0.91963 (12)	0.34611 (17)	0.64199 (9)	0.0372 (3)
C15	0.92829 (13)	0.22812 (17)	0.80845 (9)	0.0400 (3)
H15	1.0155	0.2853	0.8314	0.048*
C16	0.85082 (18)	0.2769 (2)	0.88085 (12)	0.0582 (4)
H16A	0.7633	0.2259	0.8584	0.087*
H16B	0.8408	0.3953	0.8805	0.087*
H16C	0.8994	0.2403	0.9494	0.087*
C17	0.95569 (12)	0.04323 (17)	0.81019 (9)	0.0381 (3)
C18	1.08568 (15)	−0.0187 (2)	0.84585 (12)	0.0520 (4)
H18	1.1579	0.0542	0.8700	0.062*
C19	1.11002 (18)	−0.1875 (2)	0.84623 (14)	0.0625 (4)
H19	1.1980	−0.2273	0.8705	0.075*
C20	1.00479 (19)	−0.2956 (2)	0.81091 (13)	0.0660 (4)
H20	1.0208	−0.4091	0.8111	0.079*
C21	0.87547 (19)	−0.2360 (2)	0.77518 (16)	0.0734 (5)
H21	0.8038	−0.3095	0.7506	0.088*
C22	0.85099 (15)	−0.0688 (2)	0.77539 (13)	0.0582 (4)
H22	0.7626	−0.0303	0.7518	0.070*
N1	0.65789 (11)	0.55475 (16)	0.39939 (8)	0.0449 (3)
N2	0.78681 (11)	0.52904 (15)	0.38757 (8)	0.0461 (3)
N4	0.83276 (10)	0.39916 (16)	0.54557 (8)	0.0433 (3)
N5	0.69652 (11)	0.34775 (17)	0.52228 (9)	0.0489 (3)
N3	0.64017 (12)	0.77317 (17)	0.28704 (9)	0.0520 (3)
H3	0.7215	0.7495	0.2901	0.062*
N6	0.85493 (10)	0.28577 (15)	0.70385 (8)	0.0426 (3)
H6	0.7683	0.2805	0.6819	0.051*
O1	0.45662 (10)	0.68726 (15)	0.32671 (8)	0.0580 (3)
O2	1.04136 (9)	0.36545 (14)	0.66573 (7)	0.0497 (3)

	U11	U22	U33	U12	U13	U23
C6	0.0430 (7)	0.0569 (8)	0.0349 (6)	−0.0023 (6)	0.0093 (5)	0.0085 (6)
C2	0.0442 (8)	0.0935 (14)	0.0659 (10)	−0.0094 (9)	0.0040 (7)	0.0340 (10)
C3	0.0460 (7)	0.0469 (8)	0.0368 (6)	0.0050 (6)	0.0157 (6)	0.0089 (6)
C4	0.0557 (9)	0.0945 (13)	0.0574 (9)	0.0236 (9)	0.0304 (7)	0.0280 (9)
C5	0.0440 (7)	0.0486 (8)	0.0320 (6)	0.0077 (6)	0.0122 (5)	0.0025 (6)
C1	0.0555 (8)	0.0560 (9)	0.0537 (8)	0.0184 (7)	0.0216 (7)	0.0170 (7)
C7	0.1244 (17)	0.0603 (11)	0.0657 (12)	0.0200 (12)	0.0330 (12)	0.0012 (9)
C8	0.0419 (7)	0.0415 (7)	0.0478 (7)	0.0038 (6)	0.0119 (6)	0.0127 (6)
C9	0.0425 (8)	0.0951 (14)	0.0638 (10)	0.0123 (8)	0.0133 (7)	0.0306 (10)
C10	0.0515 (9)	0.1116 (17)	0.0542 (10)	0.0021 (10)	0.0010 (7)	0.0309 (10)
C11	0.0693 (10)	0.0853 (13)	0.0443 (8)	−0.0056 (10)	0.0148 (7)	0.0120 (9)
C12	0.0543 (9)	0.0927 (13)	0.0554 (9)	0.0067 (9)	0.0209 (7)	0.0111 (9)
C13	0.0400 (7)	0.0769 (11)	0.0476 (8)	0.0076 (7)	0.0071 (6)	0.0097 (8)
C14	0.0391 (7)	0.0386 (6)	0.0332 (6)	0.0035 (5)	0.0104 (5)	0.0027 (5)
C15	0.0402 (7)	0.0460 (8)	0.0304 (6)	−0.0022 (5)	0.0068 (5)	0.0044 (5)
C16	0.0776 (11)	0.0564 (9)	0.0449 (8)	0.0074 (8)	0.0254 (7)	−0.0005 (7)
C17	0.0414 (7)	0.0457 (7)	0.0261 (6)	−0.0016 (6)	0.0093 (5)	0.0034 (5)
C18	0.0437 (8)	0.0514 (8)	0.0556 (9)	−0.0002 (6)	0.0087 (6)	0.0029 (7)
C19	0.0574 (9)	0.0585 (10)	0.0672 (10)	0.0145 (8)	0.0139 (8)	0.0049 (8)
C20	0.0843 (12)	0.0439 (9)	0.0656 (11)	0.0055 (8)	0.0182 (9)	−0.0025 (8)
C21	0.0668 (11)	0.0516 (10)	0.0899 (14)	−0.0146 (9)	0.0084 (9)	−0.0079 (9)
C22	0.0436 (8)	0.0546 (10)	0.0683 (9)	−0.0037 (7)	0.0064 (7)	−0.0005 (8)
N1	0.0406 (6)	0.0557 (7)	0.0404 (6)	0.0081 (5)	0.0156 (5)	0.0130 (5)
N2	0.0447 (6)	0.0567 (7)	0.0412 (6)	0.0093 (5)	0.0198 (5)	0.0124 (5)
N4	0.0366 (5)	0.0573 (7)	0.0352 (5)	−0.0019 (5)	0.0103 (4)	0.0103 (5)
N5	0.0384 (6)	0.0635 (7)	0.0407 (6)	−0.0066 (5)	0.0069 (5)	0.0153 (6)
N3	0.0487 (7)	0.0588 (8)	0.0535 (7)	0.0166 (6)	0.0232 (6)	0.0212 (6)
N6	0.0352 (6)	0.0533 (7)	0.0366 (6)	0.0004 (5)	0.0078 (4)	0.0116 (5)
O1	0.0446 (6)	0.0702 (7)	0.0606 (7)	0.0120 (5)	0.0189 (5)	0.0167 (6)
O2	0.0371 (5)	0.0695 (7)	0.0409 (5)	0.0005 (5)	0.0104 (4)	0.0072 (5)

C6—N5	1.2752 (18)	C11—H11	0.9300
C6—N1	1.3959 (18)	C12—C13	1.377 (2)
C6—C2	1.4935 (19)	C12—H12	0.9300
C2—H2A	0.9600	C13—H13	0.9300
C2—H2B	0.9600	C14—O2	1.2195 (15)
C2—H2C	0.9600	C14—N6	1.3351 (17)
C3—N2	1.2753 (17)	C14—N4	1.4094 (16)
C3—N4	1.4013 (16)	C15—N6	1.4684 (16)
C3—C4	1.4879 (19)	C15—C17	1.516 (2)
C4—H4A	0.9600	C15—C16	1.5210 (19)
C4—H4B	0.9600	C15—H15	0.9800
C4—H4C	0.9600	C16—H16A	0.9600
C5—O1	1.2217 (16)	C16—H16B	0.9600
C5—N3	1.3326 (18)	C16—H16C	0.9600
C5—N1	1.4098 (17)	C17—C22	1.382 (2)
C1—N3	1.4678 (19)	C17—C18	1.383 (2)
C1—C8	1.519 (2)	C18—C19	1.384 (2)
C1—C7	1.531 (3)	C18—H18	0.9300
C1—H1	0.9800	C19—C20	1.366 (3)
C7—H7A	0.9600	C19—H19	0.9300
C7—H7B	0.9600	C20—C21	1.370 (3)
C7—H7C	0.9600	C20—H20	0.9300
C8—C13	1.3738 (19)	C21—C22	1.372 (3)
C8—C9	1.383 (2)	C21—H21	0.9300
C9—C10	1.383 (2)	C22—H22	0.9300
C9—H9	0.9300	N1—N2	1.4247 (15)
C10—C11	1.361 (2)	N4—N5	1.4194 (15)
C10—H10	0.9300	N3—H3	0.8600
C11—C12	1.372 (2)	N6—H6	0.8600
N5—C6—N1	119.91 (12)	C8—C13—H13	119.3
N5—C6—C2	116.88 (13)	C12—C13—H13	119.3
N1—C6—C2	123.12 (12)	O2—C14—N6	125.18 (11)
C6—C2—H2A	109.5	O2—C14—N4	121.06 (11)
C6—C2—H2B	109.5	N6—C14—N4	113.60 (11)
H2A—C2—H2B	109.5	N6—C15—C17	111.31 (11)
C6—C2—H2C	109.5	N6—C15—C16	109.54 (12)
H2A—C2—H2C	109.5	C17—C15—C16	112.43 (12)
H2B—C2—H2C	109.5	N6—C15—H15	107.8
N2—C3—N4	119.54 (12)	C17—C15—H15	107.8
N2—C3—C4	117.96 (12)	C16—C15—H15	107.8
N4—C3—C4	122.39 (12)	C15—C16—H16A	109.5
C3—C4—H4A	109.5	C15—C16—H16B	109.5
C3—C4—H4B	109.5	H16A—C16—H16B	109.5
H4A—C4—H4B	109.5	C15—C16—H16C	109.5
C3—C4—H4C	109.5	H16A—C16—H16C	109.5
H4A—C4—H4C	109.5	H16B—C16—H16C	109.5
H4B—C4—H4C	109.5	C22—C17—C18	117.87 (14)
O1—C5—N3	124.99 (12)	C22—C17—C15	120.80 (12)
O1—C5—N1	120.43 (12)	C18—C17—C15	121.32 (12)
N3—C5—N1	114.53 (11)	C17—C18—C19	121.00 (15)
N3—C1—C8	111.78 (12)	C17—C18—H18	119.5
N3—C1—C7	109.55 (13)	C19—C18—H18	119.5
C8—C1—C7	111.00 (14)	C20—C19—C18	119.98 (16)
N3—C1—H1	108.1	C20—C19—H19	120.0
C8—C1—H1	108.1	C18—C19—H19	120.0
C7—C1—H1	108.1	C19—C20—C21	119.65 (16)
C1—C7—H7A	109.5	C19—C20—H20	120.2
C1—C7—H7B	109.5	C21—C20—H20	120.2
H7A—C7—H7B	109.5	C20—C21—C22	120.49 (16)
C1—C7—H7C	109.5	C20—C21—H21	119.8
H7A—C7—H7C	109.5	C22—C21—H21	119.8
H7B—C7—H7C	109.5	C21—C22—C17	121.00 (15)
C13—C8—C9	117.85 (14)	C21—C22—H22	119.5
C13—C8—C1	121.22 (12)	C17—C22—H22	119.5
C9—C8—C1	120.85 (13)	C6—N1—C5	125.16 (11)
C10—C9—C8	120.65 (15)	C6—N1—N2	116.52 (11)
C10—C9—H9	119.7	C5—N1—N2	115.78 (10)
C8—C9—H9	119.7	C3—N2—N1	114.83 (10)
C11—C10—C9	120.62 (15)	C3—N4—C14	126.05 (11)
C11—C10—H10	119.7	C3—N4—N5	116.58 (10)
C9—C10—H10	119.7	C14—N4—N5	114.94 (10)
C10—C11—C12	119.37 (16)	C6—N5—N4	114.68 (11)
C10—C11—H11	120.3	C5—N3—C1	121.22 (12)
C12—C11—H11	120.3	C5—N3—H3	119.4
C11—C12—C13	120.10 (15)	C1—N3—H3	119.4
C11—C12—H12	119.9	C14—N6—C15	121.52 (11)
C13—C12—H12	119.9	C14—N6—H6	119.2
C8—C13—C12	121.39 (14)	C15—N6—H6	119.2
N3—C1—C8—C13	−50.2 (2)	O1—C5—N1—C6	7.0 (2)
C7—C1—C8—C13	72.40 (19)	N3—C5—N1—C6	−175.44 (14)
N3—C1—C8—C9	132.96 (16)	O1—C5—N1—N2	168.28 (13)
C7—C1—C8—C9	−104.41 (19)	N3—C5—N1—N2	−14.20 (18)
C13—C8—C9—C10	0.4 (3)	N4—C3—N2—N1	3.17 (19)
C1—C8—C9—C10	177.27 (18)	C4—C3—N2—N1	179.28 (15)
C8—C9—C10—C11	0.2 (3)	C6—N1—N2—C3	−34.68 (18)
C9—C10—C11—C12	−0.2 (3)	C5—N1—N2—C3	162.40 (13)
C10—C11—C12—C13	−0.3 (3)	N2—C3—N4—C14	−166.55 (13)
C9—C8—C13—C12	−0.8 (3)	C4—C3—N4—C14	17.5 (2)
C1—C8—C13—C12	−177.74 (17)	N2—C3—N4—N5	32.1 (2)
C11—C12—C13—C8	0.8 (3)	C4—C3—N4—N5	−143.84 (16)
N6—C15—C17—C22	−57.93 (17)	O2—C14—N4—C3	9.7 (2)
C16—C15—C17—C22	65.39 (16)	N6—C14—N4—C3	−174.56 (14)
N6—C15—C17—C18	121.65 (14)	O2—C14—N4—N5	171.31 (13)
C16—C15—C17—C18	−115.02 (15)	N6—C14—N4—N5	−12.93 (17)
C22—C17—C18—C19	0.3 (2)	N1—C6—N5—N4	3.8 (2)
C15—C17—C18—C19	−179.33 (15)	C2—C6—N5—N4	−179.63 (15)
C17—C18—C19—C20	0.1 (3)	C3—N4—N5—C6	−35.42 (19)
C18—C19—C20—C21	0.0 (3)	C14—N4—N5—C6	161.14 (13)
C19—C20—C21—C22	−0.5 (3)	O1—C5—N3—C1	7.4 (2)
C20—C21—C22—C17	0.9 (3)	N1—C5—N3—C1	−169.98 (13)
C18—C17—C22—C21	−0.7 (2)	C8—C1—N3—C5	−126.84 (15)
C15—C17—C22—C21	178.87 (16)	C7—C1—N3—C5	109.70 (17)
N5—C6—N1—C5	−167.49 (14)	O2—C14—N6—C15	−2.9 (2)
C2—C6—N1—C5	16.2 (2)	N4—C14—N6—C15	−178.49 (12)
N5—C6—N1—N2	31.4 (2)	C17—C15—N6—C14	−93.33 (15)
C2—C6—N1—N2	−144.94 (16)	C16—C15—N6—C14	141.71 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O1i	0.86	2.44	3.2497 (15)	158
N3—H3···O2ii	0.86	2.54	3.2706 (16)	144
C13—H13···O2ii	0.93	2.57	3.4701 (17)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O1i	0.86	2.44	3.2497 (15)	158
N3—H3⋯O2ii	0.86	2.54	3.2706 (16)	144
C13—H13⋯O2ii	0.93	2.57	3.4701 (17)	163

Symmetry codes: (i) ; (ii) .