N,N′-Bis(2,6-diisopropyl­phen­yl)-3,6-di­methyl-1,2,4,5-tetra­zine-1,4-dicarboxamide

Sun, N.-B.; Rao, G.-W.; Zhang, L.-L.

doi:10.1107/S1600536812019186

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1621-o1622

doi:10.1107/S1600536812019186

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N,N′-Bis(2,6-diisopropylphenyl)-3,6-dimethyl-1,2,4,5-tetrazine-1,4-dicarboxamide

Na-Bo Sun,^a Guo-Wu Rao ^b ^* and Li-Ling Zhang ^b

^aCollege of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, People's Republic of China, and ^bCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: rgw@zjut.edu.cn

(Received 20 April 2012; accepted 29 April 2012; online 5 May 2012)

In the title molecule, C₃₀H₄₂N₆O₂, the amide-substituted N atoms of the tetrazine ring deviate from the approximate plane of the four other atoms in the ring by 0.457 (3) and 0.463 (3) Å, forming a boat conformation. The two benzene rings form a dihedral angle of 47.69 (9)°. Intramolecular N—H⋯N and weak C—H⋯O hydrogen bonds are observed.

Related literature

For chemical reactions of 1,2,4,5-tetrazine derivatives, see: Domingo et al. (2009 ); Lorincz et al. (2010 ). For their biological activity, see: Devaraj et al. (2009 ); Eremeev et al. (1978 , 1980 ); Han et al. (2010 ); Neunhoeffer (1984 ); Sauer, (1996 ). For antitumor activity of 1,2,4,5-tetrazine derivatives, see: Hu et al. (2002 , 2004 ); Rao & Hu (2005 , 2006 ). For standard bond lengths, see: Allen et al. (1987 ). For the synthesis of the title compound, see: Hu et al. (2004); Rao et al. (2012 ); Skorianetz & Kovats (1970 , 1971 ); Sun et al. (2003 ).

Experimental

Crystal data

C₃₀H₄₂N₆O₂
M_r = 518.70
Monoclinic, P 2₁ /n
a = 9.0599 (14) Å
b = 33.203 (5) Å
c = 10.8082 (17) Å
β = 112.013 (2)°
V = 3014.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.38 × 0.28 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.973, T_max = 0.986
15158 measured reflections
5304 independent reflections
3918 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.154
S = 1.05
5304 reflections
352 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2	0.86	2.18	2.588 (2)	109
N6—H6⋯N5	0.86	2.18	2.585 (2)	109
C1—H1B⋯O2	0.96	2.45	2.921 (3)	110
C2—H2B⋯O1	0.96	2.46	2.866 (3)	105

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019186/lh5460sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019186/lh5460Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019186/lh5460Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812019186/lh5460Isup4.cml

checkCIF report

Comment top

Tetrazine derivatives have high activity in chemical reactions (Domingo et al., 2009; Lorincz et al., 2010), and have been widely used in pesticides and medicines (Devaraj et al., 2009; Eremeev et al.,1978, 1980; Han et al., 2010; Neunhoeffer, 1984; Sauer, 1996). In a continuation of our studies of antitumor activities in 1,2,4,5-tetrazine derivatives (Hu et al., 2002, 2004; Rao & Hu, 2005, 2006), we have obtained a colourless crystalline compound, (I). The structure was confirmed by single-crystal X-ray diffraction.

The molecular structure of (I) is illustrated in Fig. 1. The N2═C3 [1.274 (2) Å] and N5═C6 [1.270 (2) Å] bonds are typical double bonds, and the C3—N4 [1.403 (2) Å], the N4—N5 [1.423 (2) Å], C6—N1 [1.405 (2) Å] and N1—N2 [1.424 (2) Å] bond lengths correspond to typical single bonds (Allen et al., 1987). The tetrazine ring is a 1,4-dihydro structure with the N-substituted groups at the 1,4-positions.

In (I), atoms N2, C3, N5 and C6 are approximately planar, with the largest deviation from this plane being 0.025 (1) Å. Atoms N1 and N4 deviate from this plane by -0.457 (3) and -0.463 (3) Å, respectively. The dihedral angle between the N2/C3/N5/C6 plane and the N1/N2/C6 plane is 36.75 (21)°, and between the N2/C3/N5/C6 plane and the N4/N5/C3 plane is 37.24 (12)°. The tetrazine ring has a boat conformation. The dihedral angles between the N2/C3/N5/C6 plane and the two benzene rings are 85.42 (9) and 47.28 (8)°, respectively. And the two benzene rings form a dihedral angle of 47.69 (9)°. Intramolecular N—H···N and weak C—H···O hydrogen bonds are observed.

Related literature top

For chemical reactions of 1,2,4,5-tetrazine derivatives, see: Domingo et al. (2009); Lorincz et al. (2010). For their biological activity, see: Devaraj et al. (2009); Eremeev et al. (1978, 1980); Han et al. (2010); Neunhoeffer (1984); Sauer, (1996). For antitumor activity of 1,2,4,5-tetrazine derivatives, see: Hu et al. (2002, 2004); Rao & Hu (2005, 2006). For standard bond lengths, see: Allen et al. (1987). For the synthesis of the title compound, see: Hu et al. (2004); Rao et al. (2012); Skorianetz & Kovats (1970, 1971); Sun et al. (2003).

Experimental top

The title compound was the product of the reaction of 3,6-dimethyl-1,6-dihydro-1,2,4,5-tetrazine, bis(trichloromethyl) carbonate and 2,6-diisopropylaniline according to the procedure (Hu et al., 2004; Rao et al., 2012; Skorianetz & Kovats, 1970, 1971; Sun et al., 2003). A solution of the compound in ethanol was concentrated gradually at room temperature to afford colourless blocks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).

Figures top

Fig. 1. The molecular structure of (I), shown with 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.

N,N'-Bis(2,6-diisopropylphenyl)-3,6-dimethyl-1,2,4,5-tetrazine- 1,4-dicarboxamide top

Crystal data top

C₃₀H₄₂N₆O₂	F(000) = 1120
M_r = 518.70	D_x = 1.143 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9937 reflections
a = 9.0599 (14) Å	θ = 2.4–22.7°
b = 33.203 (5) Å	µ = 0.07 mm⁻¹
c = 10.8082 (17) Å	T = 298 K
β = 112.013 (2)°	Block, colourless
V = 3014.3 (8) Å³	0.38 × 0.28 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	5304 independent reflections
Radiation source: fine-focus sealed tube	3918 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→10
T_min = 0.973, T_max = 0.986	k = −39→26
15158 measured reflections	l = −12→10

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0755P)² + 0.6253P] where P = (F_o² + 2F_c²)/3
5304 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₃₀H₄₂N₆O₂	V = 3014.3 (8) Å³
M_r = 518.70	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0599 (14) Å	µ = 0.07 mm⁻¹
b = 33.203 (5) Å	T = 298 K
c = 10.8082 (17) Å	0.38 × 0.28 × 0.20 mm
β = 112.013 (2)°

Data collection top

Bruker SMART CCD diffractometer	5304 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3918 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.986	R_int = 0.029
15158 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
5304 reflections	Δρ_min = −0.22 e Å⁻³
352 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.4285 (2)	0.09149 (5)	0.40846 (15)	0.0630 (5)
O2	0.43830 (19)	0.24162 (4)	0.01245 (15)	0.0601 (5)
N1	0.4915 (2)	0.12554 (5)	0.25237 (15)	0.0409 (4)
N2	0.4850 (2)	0.12384 (5)	0.11873 (15)	0.0423 (4)
N3	0.3522 (2)	0.06577 (5)	0.19903 (17)	0.0458 (4)
H3	0.3448	0.0704	0.1186	0.055*
N4	0.5403 (2)	0.19120 (5)	0.16262 (15)	0.0444 (4)
N5	0.6465 (2)	0.18257 (5)	0.29506 (16)	0.0448 (4)
N6	0.6382 (2)	0.25574 (5)	0.21099 (16)	0.0435 (4)
H6	0.7105	0.2450	0.2793	0.052*
C1	0.5118 (3)	0.16145 (7)	−0.0599 (2)	0.0554 (6)
H1A	0.6140	0.1715	−0.0529	0.083*
H1B	0.4301	0.1796	−0.1130	0.083*
H1C	0.4947	0.1354	−0.1013	0.083*
C2	0.7190 (3)	0.13600 (7)	0.4748 (2)	0.0549 (6)
H2A	0.7613	0.1098	0.4696	0.082*
H2B	0.6580	0.1347	0.5306	0.082*
H2C	0.8050	0.1548	0.5121	0.082*
C3	0.5067 (2)	0.15814 (6)	0.07548 (19)	0.0394 (5)
C4	0.4247 (2)	0.09282 (6)	0.2953 (2)	0.0430 (5)
C5	0.5345 (2)	0.23148 (6)	0.1203 (2)	0.0435 (5)
C6	0.6150 (2)	0.14950 (6)	0.33887 (19)	0.0403 (5)
C7	0.2869 (3)	0.02908 (6)	0.2285 (2)	0.0441 (5)
C8	0.3805 (3)	−0.00559 (6)	0.2557 (2)	0.0506 (6)
C9	0.3178 (3)	−0.04044 (7)	0.2882 (2)	0.0628 (7)
H9	0.3786	−0.0639	0.3084	0.075*
C10	0.1687 (3)	−0.04073 (8)	0.2906 (3)	0.0681 (7)
H10	0.1285	−0.0644	0.3121	0.082*
C11	0.0774 (3)	−0.00655 (8)	0.2619 (2)	0.0650 (7)
H11	−0.0245	−0.0075	0.2635	0.078*
C12	0.1332 (3)	0.02956 (7)	0.2302 (2)	0.0519 (6)
C13	0.6338 (2)	0.29878 (6)	0.19910 (19)	0.0376 (5)
C14	0.6868 (2)	0.31737 (6)	0.10760 (19)	0.0407 (5)
C15	0.6880 (3)	0.35907 (6)	0.1049 (2)	0.0480 (5)
H15	0.7230	0.3722	0.0449	0.058*
C16	0.6386 (3)	0.38145 (6)	0.1892 (2)	0.0518 (6)
H16	0.6401	0.4094	0.1857	0.062*
C17	0.5867 (3)	0.36249 (7)	0.2788 (2)	0.0516 (6)
H17	0.5540	0.3779	0.3358	0.062*
C18	0.5826 (2)	0.32085 (6)	0.2854 (2)	0.0433 (5)
C19	0.0314 (3)	0.06713 (8)	0.1971 (3)	0.0684 (7)
H19	0.1005	0.0899	0.1982	0.082*
C20	0.5466 (3)	−0.00640 (7)	0.2537 (2)	0.0585 (6)
H20	0.5678	0.0203	0.2253	0.070*
C21	0.5165 (3)	0.30030 (8)	0.3790 (2)	0.0559 (6)
H21	0.5600	0.2729	0.3944	0.067*
C22	0.7482 (3)	0.29395 (7)	0.0170 (2)	0.0551 (6)
H22	0.7259	0.2654	0.0244	0.066*
C23	−0.0464 (5)	0.07606 (12)	0.2968 (4)	0.1242 (14)
H23A	−0.0918	0.1026	0.2809	0.186*
H23B	0.0322	0.0746	0.3858	0.186*
H23C	−0.1287	0.0567	0.2865	0.186*
C24	−0.0932 (6)	0.06421 (15)	0.0601 (4)	0.161 (2)
H24A	−0.1517	0.0890	0.0380	0.241*
H24B	−0.1645	0.0425	0.0569	0.241*
H24C	−0.0435	0.0592	−0.0028	0.241*
C25	0.6701 (4)	−0.01415 (13)	0.3899 (3)	0.1023 (12)
H25A	0.7742	−0.0130	0.3860	0.153*
H25B	0.6535	−0.0403	0.4200	0.153*
H25C	0.6619	0.0059	0.4509	0.153*
C26	0.5627 (4)	−0.03696 (12)	0.1547 (3)	0.1049 (12)
H26A	0.6654	−0.0342	0.1490	0.157*
H26B	0.4812	−0.0323	0.0685	0.157*
H26C	0.5516	−0.0637	0.1842	0.157*
C27	0.3390 (3)	0.29666 (12)	0.3105 (3)	0.0984 (11)
H27A	0.2963	0.2835	0.3689	0.148*
H27B	0.3142	0.2812	0.2303	0.148*
H27C	0.2931	0.3230	0.2886	0.148*
C28	0.5620 (5)	0.32021 (13)	0.5130 (3)	0.1210 (14)
H28A	0.5167	0.3055	0.5666	0.182*
H28B	0.5226	0.3473	0.5015	0.182*
H28C	0.6758	0.3205	0.5566	0.182*
C29	0.6639 (6)	0.30637 (12)	−0.1280 (3)	0.1413 (19)
H29A	0.7050	0.2910	−0.1832	0.212*
H29B	0.6818	0.3345	−0.1374	0.212*
H29C	0.5518	0.3015	−0.1551	0.212*
C30	0.9261 (4)	0.29894 (13)	0.0624 (4)	0.1227 (15)
H30A	0.9769	0.2860	0.1472	0.184*
H30B	0.9522	0.3271	0.0708	0.184*
H30C	0.9624	0.2869	−0.0019	0.184*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0907 (13)	0.0552 (10)	0.0486 (10)	−0.0230 (9)	0.0324 (9)	−0.0020 (7)
O2	0.0637 (10)	0.0441 (9)	0.0530 (10)	−0.0064 (7)	−0.0004 (8)	0.0117 (7)
N1	0.0535 (10)	0.0331 (9)	0.0360 (9)	−0.0093 (8)	0.0167 (8)	0.0007 (7)
N2	0.0519 (10)	0.0366 (10)	0.0377 (9)	−0.0061 (8)	0.0160 (8)	−0.0002 (7)
N3	0.0583 (11)	0.0367 (10)	0.0427 (10)	−0.0117 (8)	0.0194 (8)	0.0012 (8)
N4	0.0533 (10)	0.0331 (9)	0.0368 (9)	−0.0080 (8)	0.0056 (8)	0.0046 (7)
N5	0.0497 (10)	0.0364 (10)	0.0389 (9)	−0.0066 (8)	0.0058 (8)	0.0025 (7)
N6	0.0484 (10)	0.0311 (9)	0.0439 (10)	−0.0047 (8)	0.0092 (8)	0.0049 (7)
C1	0.0665 (15)	0.0546 (14)	0.0455 (12)	−0.0111 (12)	0.0216 (11)	0.0033 (10)
C2	0.0591 (14)	0.0503 (13)	0.0451 (13)	−0.0012 (11)	0.0079 (10)	0.0064 (10)
C3	0.0403 (11)	0.0351 (11)	0.0401 (11)	−0.0057 (9)	0.0119 (9)	0.0019 (9)
C4	0.0500 (12)	0.0354 (11)	0.0453 (12)	−0.0022 (9)	0.0197 (10)	0.0041 (9)
C5	0.0455 (12)	0.0361 (11)	0.0447 (12)	−0.0050 (9)	0.0122 (10)	0.0053 (9)
C6	0.0453 (11)	0.0333 (11)	0.0397 (11)	−0.0028 (9)	0.0130 (9)	0.0014 (9)
C7	0.0515 (13)	0.0359 (11)	0.0423 (11)	−0.0139 (10)	0.0146 (10)	−0.0008 (9)
C8	0.0575 (14)	0.0415 (12)	0.0492 (13)	−0.0113 (11)	0.0159 (10)	0.0008 (10)
C9	0.0733 (18)	0.0395 (13)	0.0695 (16)	−0.0113 (12)	0.0198 (13)	0.0071 (11)
C10	0.0767 (19)	0.0516 (16)	0.0702 (17)	−0.0283 (14)	0.0210 (14)	0.0079 (12)
C11	0.0538 (14)	0.0732 (18)	0.0658 (16)	−0.0249 (14)	0.0200 (12)	0.0025 (13)
C12	0.0498 (13)	0.0547 (14)	0.0485 (13)	−0.0134 (11)	0.0151 (10)	−0.0016 (10)
C13	0.0372 (10)	0.0303 (10)	0.0420 (11)	−0.0039 (8)	0.0109 (9)	0.0016 (8)
C14	0.0436 (11)	0.0369 (11)	0.0405 (11)	−0.0039 (9)	0.0145 (9)	0.0018 (9)
C15	0.0536 (13)	0.0393 (12)	0.0529 (13)	−0.0037 (10)	0.0220 (10)	0.0080 (10)
C16	0.0532 (13)	0.0313 (11)	0.0684 (15)	−0.0022 (10)	0.0201 (11)	0.0027 (10)
C17	0.0533 (13)	0.0421 (13)	0.0603 (14)	0.0061 (10)	0.0225 (11)	−0.0027 (11)
C18	0.0370 (11)	0.0458 (12)	0.0453 (12)	0.0015 (9)	0.0133 (9)	0.0042 (9)
C19	0.0544 (15)	0.0691 (17)	0.0824 (19)	−0.0005 (13)	0.0263 (13)	0.0042 (14)
C20	0.0624 (15)	0.0440 (13)	0.0693 (16)	−0.0008 (11)	0.0247 (12)	0.0060 (11)
C21	0.0591 (14)	0.0615 (15)	0.0561 (14)	0.0047 (11)	0.0320 (12)	0.0100 (11)
C22	0.0736 (16)	0.0491 (13)	0.0507 (13)	−0.0040 (12)	0.0324 (12)	−0.0005 (10)
C23	0.149 (4)	0.111 (3)	0.135 (3)	0.018 (3)	0.079 (3)	−0.018 (2)
C24	0.176 (4)	0.157 (4)	0.087 (3)	0.081 (4)	−0.022 (3)	−0.010 (3)
C25	0.0665 (19)	0.168 (4)	0.067 (2)	−0.019 (2)	0.0188 (15)	−0.009 (2)
C26	0.085 (2)	0.139 (3)	0.088 (2)	0.010 (2)	0.0287 (18)	−0.029 (2)
C27	0.0706 (19)	0.142 (3)	0.094 (2)	−0.0177 (19)	0.0439 (17)	0.028 (2)
C28	0.150 (3)	0.166 (4)	0.0577 (19)	−0.048 (3)	0.052 (2)	−0.009 (2)
C29	0.260 (6)	0.115 (3)	0.0521 (18)	0.059 (3)	0.063 (3)	0.0101 (19)
C30	0.090 (2)	0.136 (3)	0.176 (4)	−0.023 (2)	0.089 (3)	−0.070 (3)

Geometric parameters (Å, º) top

O1—C4	1.211 (2)	C16—C17	1.377 (3)
O2—C5	1.212 (2)	C16—H16	0.9300
N1—C6	1.405 (2)	C17—C18	1.386 (3)
N1—C4	1.405 (2)	C17—H17	0.9300
N1—N2	1.424 (2)	C18—C21	1.517 (3)
N2—C3	1.274 (2)	C19—C24	1.492 (4)
N3—C4	1.345 (3)	C19—C23	1.521 (4)
N3—C7	1.441 (2)	C19—H19	0.9800
N3—H3	0.8600	C20—C25	1.500 (4)
N4—C3	1.403 (2)	C20—C26	1.521 (4)
N4—C5	1.408 (2)	C20—H20	0.9800
N4—N5	1.423 (2)	C21—C27	1.502 (4)
N5—C6	1.270 (2)	C21—C28	1.502 (4)
N6—C5	1.342 (3)	C21—H21	0.9800
N6—C13	1.434 (2)	C22—C30	1.508 (4)
N6—H6	0.8600	C22—C29	1.521 (4)
C1—C3	1.486 (3)	C22—H22	0.9800
C1—H1A	0.9600	C23—H23A	0.9600
C1—H1B	0.9600	C23—H23B	0.9600
C1—H1C	0.9600	C23—H23C	0.9600
C2—C6	1.487 (3)	C24—H24A	0.9600
C2—H2A	0.9600	C24—H24B	0.9600
C2—H2B	0.9600	C24—H24C	0.9600
C2—H2C	0.9600	C25—H25A	0.9600
C7—C8	1.394 (3)	C25—H25B	0.9600
C7—C12	1.400 (3)	C25—H25C	0.9600
C8—C9	1.390 (3)	C26—H26A	0.9600
C8—C20	1.514 (3)	C26—H26B	0.9600
C9—C10	1.361 (4)	C26—H26C	0.9600
C9—H9	0.9300	C27—H27A	0.9600
C10—C11	1.370 (4)	C27—H27B	0.9600
C10—H10	0.9300	C27—H27C	0.9600
C11—C12	1.393 (3)	C28—H28A	0.9600
C11—H11	0.9300	C28—H28B	0.9600
C12—C19	1.512 (3)	C28—H28C	0.9600
C13—C14	1.395 (3)	C29—H29A	0.9600
C13—C18	1.395 (3)	C29—H29B	0.9600
C14—C15	1.385 (3)	C29—H29C	0.9600
C14—C22	1.511 (3)	C30—H30A	0.9600
C15—C16	1.374 (3)	C30—H30B	0.9600
C15—H15	0.9300	C30—H30C	0.9600

C6—N1—C4	123.52 (16)	C13—C18—C21	121.51 (19)
C6—N1—N2	114.68 (15)	C24—C19—C12	110.4 (2)
C4—N1—N2	116.42 (15)	C24—C19—C23	109.7 (3)
C3—N2—N1	112.52 (16)	C12—C19—C23	113.4 (3)
C4—N3—C7	121.03 (17)	C24—C19—H19	107.7
C4—N3—H3	119.5	C12—C19—H19	107.7
C7—N3—H3	119.5	C23—C19—H19	107.7
C3—N4—C5	123.54 (16)	C25—C20—C8	111.7 (2)
C3—N4—N5	114.38 (16)	C25—C20—C26	110.1 (3)
C5—N4—N5	116.55 (15)	C8—C20—C26	112.3 (2)
C6—N5—N4	112.80 (16)	C25—C20—H20	107.5
C5—N6—C13	122.97 (16)	C8—C20—H20	107.5
C5—N6—H6	118.5	C26—C20—H20	107.5
C13—N6—H6	118.5	C27—C21—C28	111.5 (3)
C3—C1—H1A	109.5	C27—C21—C18	108.96 (19)
C3—C1—H1B	109.5	C28—C21—C18	114.2 (2)
H1A—C1—H1B	109.5	C27—C21—H21	107.3
C3—C1—H1C	109.5	C28—C21—H21	107.3
H1A—C1—H1C	109.5	C18—C21—H21	107.3
H1B—C1—H1C	109.5	C30—C22—C14	109.9 (2)
C6—C2—H2A	109.5	C30—C22—C29	111.6 (3)
C6—C2—H2B	109.5	C14—C22—C29	111.3 (2)
H2A—C2—H2B	109.5	C30—C22—H22	107.9
C6—C2—H2C	109.5	C14—C22—H22	107.9
H2A—C2—H2C	109.5	C29—C22—H22	107.9
H2B—C2—H2C	109.5	C19—C23—H23A	109.5
N2—C3—N4	118.53 (17)	C19—C23—H23B	109.5
N2—C3—C1	119.58 (18)	H23A—C23—H23B	109.5
N4—C3—C1	121.60 (17)	C19—C23—H23C	109.5
O1—C4—N3	125.31 (19)	H23A—C23—H23C	109.5
O1—C4—N1	120.60 (18)	H23B—C23—H23C	109.5
N3—C4—N1	114.00 (18)	C19—C24—H24A	109.5
O2—C5—N6	126.14 (19)	C19—C24—H24B	109.5
O2—C5—N4	120.12 (18)	H24A—C24—H24B	109.5
N6—C5—N4	113.69 (17)	C19—C24—H24C	109.5
N5—C6—N1	118.39 (17)	H24A—C24—H24C	109.5
N5—C6—C2	118.78 (18)	H24B—C24—H24C	109.5
N1—C6—C2	122.60 (17)	C20—C25—H25A	109.5
C8—C7—C12	122.39 (19)	C20—C25—H25B	109.5
C8—C7—N3	118.50 (19)	H25A—C25—H25B	109.5
C12—C7—N3	119.11 (19)	C20—C25—H25C	109.5
C9—C8—C7	117.9 (2)	H25A—C25—H25C	109.5
C9—C8—C20	119.4 (2)	H25B—C25—H25C	109.5
C7—C8—C20	122.74 (19)	C20—C26—H26A	109.5
C10—C9—C8	120.9 (2)	C20—C26—H26B	109.5
C10—C9—H9	119.6	H26A—C26—H26B	109.5
C8—C9—H9	119.6	C20—C26—H26C	109.5
C9—C10—C11	120.6 (2)	H26A—C26—H26C	109.5
C9—C10—H10	119.7	H26B—C26—H26C	109.5
C11—C10—H10	119.7	C21—C27—H27A	109.5
C10—C11—C12	121.7 (2)	C21—C27—H27B	109.5
C10—C11—H11	119.2	H27A—C27—H27B	109.5
C12—C11—H11	119.2	C21—C27—H27C	109.5
C11—C12—C7	116.6 (2)	H27A—C27—H27C	109.5
C11—C12—C19	121.5 (2)	H27B—C27—H27C	109.5
C7—C12—C19	121.8 (2)	C21—C28—H28A	109.5
C14—C13—C18	122.05 (18)	C21—C28—H28B	109.5
C14—C13—N6	119.95 (17)	H28A—C28—H28B	109.5
C18—C13—N6	117.94 (17)	C21—C28—H28C	109.5
C15—C14—C13	117.70 (19)	H28A—C28—H28C	109.5
C15—C14—C22	119.55 (18)	H28B—C28—H28C	109.5
C13—C14—C22	122.70 (18)	C22—C29—H29A	109.5
C16—C15—C14	121.3 (2)	C22—C29—H29B	109.5
C16—C15—H15	119.3	H29A—C29—H29B	109.5
C14—C15—H15	119.3	C22—C29—H29C	109.5
C15—C16—C17	120.0 (2)	H29A—C29—H29C	109.5
C15—C16—H16	120.0	H29B—C29—H29C	109.5
C17—C16—H16	120.0	C22—C30—H30A	109.5
C16—C17—C18	121.0 (2)	C22—C30—H30B	109.5
C16—C17—H17	119.5	H30A—C30—H30B	109.5
C18—C17—H17	119.5	C22—C30—H30C	109.5
C17—C18—C13	117.86 (19)	H30A—C30—H30C	109.5
C17—C18—C21	120.6 (2)	H30B—C30—H30C	109.5

C6—N1—N2—C3	−42.8 (2)	C10—C11—C12—C7	0.4 (3)
C4—N1—N2—C3	162.07 (18)	C10—C11—C12—C19	179.4 (2)
C3—N4—N5—C6	−43.5 (2)	C8—C7—C12—C11	0.5 (3)
C5—N4—N5—C6	161.71 (19)	N3—C7—C12—C11	−178.75 (19)
N1—N2—C3—N4	2.9 (3)	C8—C7—C12—C19	−178.5 (2)
N1—N2—C3—C1	176.89 (17)	N3—C7—C12—C19	2.3 (3)
C5—N4—C3—N2	−166.59 (19)	C5—N6—C13—C14	−74.7 (3)
N5—N4—C3—N2	40.6 (3)	C5—N6—C13—C18	108.2 (2)
C5—N4—C3—C1	19.6 (3)	C18—C13—C14—C15	0.3 (3)
N5—N4—C3—C1	−133.2 (2)	N6—C13—C14—C15	−176.64 (17)
C7—N3—C4—O1	−7.7 (3)	C18—C13—C14—C22	177.70 (19)
C7—N3—C4—N1	175.78 (18)	N6—C13—C14—C22	0.8 (3)
C6—N1—C4—O1	25.7 (3)	C13—C14—C15—C16	−0.1 (3)
N2—N1—C4—O1	178.37 (19)	C22—C14—C15—C16	−177.6 (2)
C6—N1—C4—N3	−157.65 (18)	C14—C15—C16—C17	0.1 (3)
N2—N1—C4—N3	−5.0 (3)	C15—C16—C17—C18	−0.3 (3)
C13—N6—C5—O2	8.8 (3)	C16—C17—C18—C13	0.5 (3)
C13—N6—C5—N4	−168.69 (17)	C16—C17—C18—C21	−176.5 (2)
C3—N4—C5—O2	33.3 (3)	C14—C13—C18—C17	−0.5 (3)
N5—N4—C5—O2	−174.45 (19)	N6—C13—C18—C17	176.52 (18)
C3—N4—C5—N6	−149.00 (19)	C14—C13—C18—C21	176.49 (18)
N5—N4—C5—N6	3.2 (3)	N6—C13—C18—C21	−6.5 (3)
N4—N5—C6—N1	3.7 (3)	C11—C12—C19—C24	−75.3 (4)
N4—N5—C6—C2	178.32 (18)	C7—C12—C19—C24	103.7 (3)
C4—N1—C6—N5	−166.90 (19)	C11—C12—C19—C23	48.3 (4)
N2—N1—C6—N5	40.0 (3)	C7—C12—C19—C23	−132.8 (3)
C4—N1—C6—C2	18.7 (3)	C9—C8—C20—C25	−64.7 (3)
N2—N1—C6—C2	−134.4 (2)	C7—C8—C20—C25	114.2 (3)
C4—N3—C7—C8	−94.6 (2)	C9—C8—C20—C26	59.5 (3)
C4—N3—C7—C12	84.7 (2)	C7—C8—C20—C26	−121.6 (3)
C12—C7—C8—C9	−1.3 (3)	C17—C18—C21—C27	85.4 (3)
N3—C7—C8—C9	177.98 (19)	C13—C18—C21—C27	−91.5 (3)
C12—C7—C8—C20	179.8 (2)	C17—C18—C21—C28	−40.1 (3)
N3—C7—C8—C20	−0.9 (3)	C13—C18—C21—C28	143.1 (3)
C7—C8—C9—C10	1.2 (3)	C15—C14—C22—C30	69.4 (3)
C20—C8—C9—C10	−179.9 (2)	C13—C14—C22—C30	−107.9 (3)
C8—C9—C10—C11	−0.3 (4)	C15—C14—C22—C29	−54.8 (3)
C9—C10—C11—C12	−0.5 (4)	C13—C14—C22—C29	127.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.86	2.18	2.588 (2)	109
N6—H6···N5	0.86	2.18	2.585 (2)	109
C1—H1B···O2	0.96	2.45	2.921 (3)	110
C2—H2B···O1	0.96	2.46	2.866 (3)	105

Experimental details

Crystal data
Chemical formula	C₃₀H₄₂N₆O₂
M_r	518.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.0599 (14), 33.203 (5), 10.8082 (17)
β (°)	112.013 (2)
V (Å³)	3014.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.38 × 0.28 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.973, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	15158, 5304, 3918
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.154, 1.05
No. of reflections	5304
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.86	2.18	2.588 (2)	108.7
N6—H6···N5	0.86	2.18	2.585 (2)	108.9
C1—H1B···O2	0.96	2.45	2.921 (3)	109.9
C2—H2B···O1	0.96	2.46	2.866 (3)	105.0

Acknowledgements

The authors are grateful to the Natural Science Foundation of Zhejiang Province (No. Y2090985) and the Program of Education Department of Zhejiang Province of China (Y200803060) for financial support.

References

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Volume 68| Part 6| June 2012| Pages o1621-o1622

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

N,N′-Bis(2,6-diiso­propyl­phen­yl)-3,6-di­methyl-1,2,4,5-tetra­zine-1,4-dicarboxamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

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organic compounds

N,N′-Bis(2,6-diisopropylphenyl)-3,6-dimethyl-1,2,4,5-tetrazine-1,4-dicarboxamide