N,N'-Bis(2,6-diisopropyl-phen-yl)-3,6-di-methyl-1,2,4,5-tetra-zine-1,4-dicarboxamide.

In the title mol-ecule, C(30)H(42)N(6)O(2), the amide-substituted N atoms of the tetra-zine ring deviate from the approximate plane of the four other atoms in the ring by 0.457 (3) and 0.463 (3) Å, forming a boat conformation. The two benzene rings form a dihedral angle of 47.69 (9)°. Intra-molecular 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 = 518.70

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.154

S = 1.05

5304 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 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/S1600536812019186/lh5460sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812019186/lh5460Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812019186/lh5460Isup4.cml

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

C30H42N6O2	F(000) = 1120
Mr = 518.70	Dx = 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

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

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(Fo2) + (0.0755P)2 + 0.6253P] where P = (Fo2 + 2Fc2)/3
5304 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 e Å−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
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*

	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)

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)

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

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