6-Methyl-N-(2-methyl-phen-yl)-3-phenyl-1,6-dihydro-1,2,4,5-tetra-zine-1-carbox-amide.

In the title compound, C(17)H(16)N(5)O, the central tetra-zine ring adopts an unsymmetrical boat conformation with the two C atoms as flagpoles. This compound can be considered as having homoaromaticity. The crystal structure is stabilized by inter-molecular C-H⋯O inter-actions between a benzene H atom and the carbonyl O atom.

Related literature

For related literature, see: Hu et al. (2004 ▶, 2005 ▶); Jennison et al. (1986 ▶); Sauer (1996 ▶); Stam et al. (1982 ▶); Xu et al. (2006 ▶).

Experimental

Crystal data

C17H16N5O

M = 306.35

Monoclinic,

a = 13.941 (6) Å

b = 5.675 (2) Å

c = 20.614 (8) Å

β = 102.055 (6)°

V = 1594.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 291 (2) K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.995

6815 measured reflections

3116 independent reflections

1882 reflections with I > 2σ(I)

R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.193

S = 0.94

3116 reflections

226 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020199/lx2060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020199/lx2060Isup2.hkl

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

C17H16N5O	F000 = 644
Mr = 306.35	Dx = 1.276 Mg m−3
Monoclinic, P21/c	Melting point = 378–380 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 13.941 (6) Å	Cell parameters from 742 reflections
b = 5.675 (2) Å	θ = 3.2–24.8º
c = 20.614 (8) Å	µ = 0.08 mm−1
β = 102.055 (6)º	T = 291 (2) K
V = 1594.9 (11) Å3	Prism, red
Z = 4	0.12 × 0.10 × 0.06 mm

Bruker SMART APEX CCD area-detector diffractometer	3116 independent reflections
Radiation source: fine-focus sealed tube	1882 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.084
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 1.5º
φ and ω scans	h = −17→8
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −6→7
Tmin = 0.980, Tmax = 0.995	l = −25→25
6815 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.072	w = 1/[σ2(Fo2) + (0.1133P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.193	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.54 e Å−3
3116 reflections	Δρmin = −0.31 e Å−3
226 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (5)
Secondary atom site location: difference Fourier map

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
O	0.79549 (13)	0.2358 (3)	0.73526 (8)	0.0685 (5)
N1	0.82379 (14)	0.4541 (3)	0.64939 (9)	0.0552 (5)
N2	0.79315 (13)	0.5181 (3)	0.58485 (9)	0.0522 (5)
N3	0.88534 (17)	0.8632 (4)	0.61618 (12)	0.0685 (6)
N4	0.91853 (17)	0.7948 (4)	0.67409 (12)	0.0724 (6)
N5	0.68918 (15)	0.2115 (4)	0.63448 (10)	0.0598 (6)
H5N	0.6759 (17)	0.282 (4)	0.5967 (12)	0.054 (6)*
C1	0.91906 (18)	0.5354 (4)	0.68427 (11)	0.0587 (6)
C2	0.83633 (17)	0.7032 (4)	0.56768 (11)	0.0526 (6)
C3	0.82173 (17)	0.7755 (4)	0.49788 (12)	0.0542 (6)
C4	0.77371 (19)	0.6256 (5)	0.44798 (12)	0.0644 (7)
H4	0.7490	0.4824	0.4592	0.077*
C5	0.7624 (2)	0.6873 (6)	0.38197 (14)	0.0813 (9)
H5	0.7307	0.5853	0.3491	0.098*
C6	0.7975 (2)	0.8971 (6)	0.36496 (16)	0.0825 (9)
H6	0.7889	0.9392	0.3205	0.099*
C7	0.8452 (3)	1.0452 (6)	0.41287 (18)	0.0876 (10)
H7	0.8701	1.1870	0.4009	0.105*
C8	0.8571 (2)	0.9862 (5)	0.47985 (15)	0.0788 (8)
H8	0.8889	1.0897	0.5123	0.095*
C9	0.76906 (18)	0.2904 (4)	0.67787 (11)	0.0535 (6)
C10	0.61865 (18)	0.0506 (4)	0.64801 (11)	0.0559 (6)
C11	0.6437 (2)	−0.1223 (5)	0.69669 (13)	0.0724 (8)
H11	0.7077	−0.1329	0.7210	0.087*
C12	0.5740 (3)	−0.2762 (6)	0.70856 (15)	0.0883 (10)
H12	0.5905	−0.3910	0.7412	0.106*
C13	0.4807 (3)	−0.2619 (6)	0.67292 (18)	0.0928 (11)
H13	0.4330	−0.3646	0.6817	0.111*
C14	0.4564 (2)	−0.0944 (6)	0.62345 (16)	0.0817 (9)
H14	0.3926	−0.0891	0.5987	0.098*
C15	0.52429 (19)	0.0652 (4)	0.60974 (12)	0.0601 (7)
C16	1.00241 (18)	0.4238 (5)	0.65920 (13)	0.0658 (7)
H16A	1.0013	0.2564	0.6656	0.099*
H16B	1.0636	0.4865	0.6832	0.099*
H16C	0.9955	0.4575	0.6128	0.099*
C17	0.4969 (3)	0.2482 (6)	0.55605 (17)	0.0790 (8)
H17A	0.431 (3)	0.232 (5)	0.5290 (16)	0.102 (10)*
H17B	0.543 (2)	0.223 (5)	0.5212 (15)	0.092 (9)*
H17C	0.511 (3)	0.408 (7)	0.5726 (16)	0.107 (11)*

	U11	U22	U33	U12	U13	U23
O	0.0755 (12)	0.0808 (13)	0.0475 (10)	−0.0050 (9)	0.0090 (8)	0.0014 (7)
N1	0.0491 (11)	0.0653 (12)	0.0486 (10)	−0.0056 (10)	0.0039 (8)	0.0001 (8)
N2	0.0469 (11)	0.0556 (11)	0.0529 (11)	−0.0018 (9)	0.0077 (8)	0.0026 (8)
N3	0.0682 (14)	0.0511 (12)	0.0823 (15)	−0.0009 (10)	0.0067 (12)	−0.0101 (10)
N4	0.0740 (15)	0.0636 (14)	0.0742 (15)	−0.0012 (11)	0.0030 (12)	−0.0181 (11)
N5	0.0537 (12)	0.0737 (14)	0.0501 (12)	−0.0109 (10)	0.0064 (10)	0.0102 (9)
C1	0.0521 (15)	0.0578 (14)	0.0616 (14)	−0.0068 (12)	0.0015 (11)	−0.0095 (10)
C2	0.0488 (13)	0.0424 (12)	0.0658 (14)	0.0002 (11)	0.0098 (11)	−0.0017 (9)
C3	0.0427 (13)	0.0485 (13)	0.0722 (15)	0.0022 (10)	0.0137 (11)	0.0085 (10)
C4	0.0610 (16)	0.0681 (16)	0.0637 (15)	−0.0068 (13)	0.0123 (12)	0.0116 (11)
C5	0.0763 (19)	0.101 (2)	0.0649 (16)	−0.0060 (17)	0.0117 (14)	0.0133 (14)
C6	0.0736 (19)	0.095 (2)	0.0832 (19)	0.0109 (18)	0.0271 (16)	0.0321 (17)
C7	0.094 (2)	0.0653 (19)	0.115 (3)	−0.0012 (17)	0.047 (2)	0.0308 (17)
C8	0.084 (2)	0.0583 (17)	0.098 (2)	−0.0070 (15)	0.0271 (16)	0.0097 (14)
C9	0.0520 (14)	0.0604 (14)	0.0484 (13)	0.0014 (11)	0.0111 (11)	−0.0033 (10)
C10	0.0597 (15)	0.0570 (14)	0.0548 (13)	−0.0092 (12)	0.0210 (11)	−0.0027 (10)
C11	0.0846 (19)	0.0703 (17)	0.0646 (15)	−0.0100 (15)	0.0209 (14)	0.0082 (12)
C12	0.119 (3)	0.080 (2)	0.0732 (18)	−0.028 (2)	0.035 (2)	0.0027 (14)
C13	0.106 (3)	0.089 (2)	0.097 (2)	−0.042 (2)	0.053 (2)	−0.0174 (18)
C14	0.0644 (18)	0.090 (2)	0.096 (2)	−0.0193 (16)	0.0277 (16)	−0.0261 (17)
C15	0.0571 (16)	0.0621 (15)	0.0645 (14)	−0.0049 (12)	0.0205 (12)	−0.0115 (11)
C16	0.0513 (15)	0.0635 (16)	0.0779 (16)	−0.0031 (12)	0.0029 (12)	0.0007 (11)
C17	0.064 (2)	0.078 (2)	0.087 (2)	0.0031 (17)	−0.0032 (17)	−0.0037 (16)

O—C9	1.204 (3)	C7—C8	1.397 (4)
N1—N2	1.359 (3)	C7—H7	0.9300
N1—C9	1.406 (3)	C8—H8	0.9300
N1—C1	1.447 (3)	C10—C15	1.388 (4)
N2—C2	1.296 (3)	C10—C11	1.395 (4)
N3—N4	1.249 (3)	C11—C12	1.366 (4)
N3—C2	1.416 (3)	C11—H11	0.9300
N4—C1	1.487 (3)	C12—C13	1.356 (5)
N5—C9	1.351 (3)	C12—H12	0.9300
N5—C10	1.412 (3)	C13—C14	1.383 (5)
N5—H5N	0.86 (2)	C13—H13	0.9300
C1—C16	1.506 (3)	C14—C15	1.381 (4)
C2—C3	1.469 (3)	C14—H14	0.9300
C3—C8	1.374 (4)	C15—C17	1.508 (4)
C3—C4	1.394 (4)	C16—H16A	0.9600
C4—C5	1.382 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.361 (4)	C17—H17A	0.98 (4)
C5—H5	0.9300	C17—H17B	1.07 (3)
C6—C7	1.360 (5)	C17—H17C	0.97 (4)
C6—H6	0.9300
N2—N1—C9	119.9 (2)	O—C9—N5	127.3 (2)
N2—N1—C1	118.0 (2)	O—C9—N1	119.9 (2)
C9—N1—C1	121.7 (2)	N5—C9—N1	112.8 (2)
C2—N2—N1	114.5 (2)	C15—C10—C11	121.1 (2)
N4—N3—C2	120.2 (2)	C15—C10—N5	117.7 (2)
N3—N4—C1	115.6 (2)	C11—C10—N5	121.1 (2)
C9—N5—C10	126.5 (2)	C12—C11—C10	119.9 (3)
C9—N5—H5N	115.8 (16)	C12—C11—H11	120.1
C10—N5—H5N	117.0 (16)	C10—C11—H11	120.1
N1—C1—N4	105.6 (2)	C13—C12—C11	120.2 (3)
N1—C1—C16	112.9 (2)	C13—C12—H12	119.9
N4—C1—C16	110.4 (2)	C11—C12—H12	119.9
N2—C2—N3	120.7 (2)	C12—C13—C14	120.0 (3)
N2—C2—C3	121.1 (2)	C12—C13—H13	120.0
N3—C2—C3	117.4 (2)	C14—C13—H13	120.0
C8—C3—C4	118.4 (2)	C15—C14—C13	122.0 (3)
C8—C3—C2	121.6 (2)	C15—C14—H14	119.0
C4—C3—C2	120.0 (2)	C13—C14—H14	119.0
C5—C4—C3	120.7 (2)	C14—C15—C10	116.9 (2)
C5—C4—H4	119.7	C14—C15—C17	121.5 (3)
C3—C4—H4	119.7	C10—C15—C17	121.5 (2)
C6—C5—C4	120.2 (3)	C1—C16—H16A	109.5
C6—C5—H5	119.9	C1—C16—H16B	109.5
C4—C5—H5	119.9	H16A—C16—H16B	109.5
C7—C6—C5	120.1 (3)	C1—C16—H16C	109.5
C7—C6—H6	120.0	H16A—C16—H16C	109.5
C5—C6—H6	120.0	H16B—C16—H16C	109.5
C6—C7—C8	120.6 (3)	C15—C17—H17A	114.5 (19)
C6—C7—H7	119.7	C15—C17—H17B	107.6 (16)
C8—C7—H7	119.7	H17A—C17—H17B	104 (2)
C3—C8—C7	120.1 (3)	C15—C17—H17C	112.6 (19)
C3—C8—H8	120.0	H17A—C17—H17C	113 (3)
C7—C8—H8	120.0	H17B—C17—H17C	105 (3)
C9—N1—N2—C2	166.3 (2)	C4—C3—C8—C7	−0.5 (4)
C1—N1—N2—C2	−21.5 (3)	C2—C3—C8—C7	177.5 (3)
C2—N3—N4—C1	10.6 (3)	C6—C7—C8—C3	1.0 (5)
N2—N1—C1—N4	52.3 (3)	C10—N5—C9—O	1.3 (4)
C9—N1—C1—N4	−135.5 (2)	C10—N5—C9—N1	−178.6 (2)
N2—N1—C1—C16	−68.4 (3)	N2—N1—C9—O	−179.1 (2)
C9—N1—C1—C16	103.7 (2)	C1—N1—C9—O	8.9 (3)
N3—N4—C1—N1	−45.4 (3)	N2—N1—C9—N5	0.8 (3)
N3—N4—C1—C16	77.0 (3)	C1—N1—C9—N5	−171.2 (2)
N1—N2—C2—N3	−19.4 (3)	C9—N5—C10—C15	152.7 (2)
N1—N2—C2—C3	171.32 (19)	C9—N5—C10—C11	−29.4 (4)
N4—N3—C2—N2	25.8 (3)	C15—C10—C11—C12	−2.0 (4)
N4—N3—C2—C3	−164.6 (2)	N5—C10—C11—C12	−179.8 (2)
N2—C2—C3—C8	171.8 (2)	C10—C11—C12—C13	0.3 (4)
N3—C2—C3—C8	2.2 (3)	C11—C12—C13—C14	1.4 (5)
N2—C2—C3—C4	−10.2 (4)	C12—C13—C14—C15	−1.6 (5)
N3—C2—C3—C4	−179.8 (2)	C13—C14—C15—C10	0.0 (4)
C8—C3—C4—C5	0.3 (4)	C13—C14—C15—C17	−179.5 (3)
C2—C3—C4—C5	−177.7 (2)	C11—C10—C15—C14	1.8 (3)
C3—C4—C5—C6	−0.5 (4)	N5—C10—C15—C14	179.7 (2)
C4—C5—C6—C7	1.0 (5)	C11—C10—C15—C17	−178.7 (3)
C5—C6—C7—C8	−1.2 (5)	N5—C10—C15—C17	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Oi	0.93	2.56	3.385 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Oi	0.93	2.56	3.385 (3)	148

Symmetry code: (i) .