3,6-Bis(4-chloro-phen-yl)-N,N-bis-(1-phenyl-eth-yl)-1,2,4,5-tetra-zine-1,4-di-carboxamide.

In the title mol-ecule, C(32)H(28)Cl(2)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 0.468 (3) and 0.484 (3) Å, forming a boat conformation. The dihedral angle between the two phenyl rings is 67.0 (1)° and that between the two chloro-substituted benzene rings is 73.8 (1)°. Two intra-molecular N-H⋯N 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 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 standard bond lengths, see: Allen et al. (1987 ▶). For the synthesis of the title compound, see: Abdel-rahman et al. (1968 ▶); Hu et al. (2004 ▶); Rao & Hu (2006 ▶).

Experimental

Crystal data

C32H28Cl2N6O2

M = 599.50

Orthorhombic,

a = 9.715 (2) Å

b = 14.725 (3) Å

c = 21.159 (5) Å

V = 3027.0 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.23 × 0.19 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.944, T max = 0.970

19445 measured reflections

7314 independent reflections

4680 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 1.01

7314 reflections

380 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), with 3185 Friedel pairs

Flack parameter: 0.03 (5)

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/S1600536812003765/lh5409sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812003765/lh5409Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003765/lh5409Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812003765/lh5409Isup4.cml

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

C32H28Cl2N6O2	F(000) = 1248
Mr = 599.50	Dx = 1.316 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4171 reflections
a = 9.715 (2) Å	θ = 2.5–21.5°
b = 14.725 (3) Å	µ = 0.25 mm−1
c = 21.159 (5) Å	T = 298 K
V = 3027.0 (12) Å3	Block, yellow
Z = 4	0.23 × 0.19 × 0.12 mm

Bruker SMART CCD diffractometer	7314 independent reflections
Radiation source: fine-focus sealed tube	4680 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→12
Tmin = 0.944, Tmax = 0.970	k = −19→17
19445 measured reflections	l = −27→23

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0431P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.13 e Å−3
7314 reflections	Δρmin = −0.15 e Å−3
380 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0032 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 3185 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.03 (5)

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
Cl1	0.97748 (8)	0.65714 (4)	0.24050 (3)	0.0762 (2)
Cl2	1.29647 (10)	1.51972 (5)	0.14950 (5)	0.1031 (3)
O1	1.00558 (16)	0.89564 (10)	0.01136 (7)	0.0586 (4)
N2	1.06405 (18)	1.12227 (11)	0.05805 (8)	0.0481 (4)
C9	0.9347 (2)	0.92381 (13)	0.13933 (9)	0.0413 (4)
N1	0.99625 (16)	1.03724 (10)	0.05423 (7)	0.0456 (4)
C12	0.9598 (2)	0.76006 (14)	0.20118 (10)	0.0504 (5)
N4	0.85399 (17)	1.15911 (11)	0.10225 (8)	0.0458 (4)
C14	0.8196 (2)	0.87854 (15)	0.16048 (10)	0.0499 (5)
H14	0.7329	0.9036	0.1539	0.060*
N5	0.84906 (17)	1.07490 (11)	0.13578 (8)	0.0470 (4)
C6	0.92133 (19)	1.01363 (13)	0.10807 (9)	0.0422 (5)
C3	0.9867 (2)	1.18387 (13)	0.08194 (9)	0.0443 (5)
C15	1.0540 (2)	0.97121 (14)	0.01349 (9)	0.0464 (5)
C13	0.8316 (2)	0.79653 (15)	0.19127 (11)	0.0542 (6)
H13	0.7535	0.7661	0.2052	0.065*
O2	0.73843 (16)	1.29115 (10)	0.08359 (8)	0.0599 (4)
C16	0.7439 (2)	1.21948 (15)	0.11254 (10)	0.0496 (5)
C11	1.0759 (2)	0.80464 (16)	0.18125 (11)	0.0594 (6)
H11	1.1625	0.7800	0.1886	0.071*
C21	1.3807 (2)	0.92538 (15)	−0.03766 (10)	0.0486 (5)
C10	1.0625 (2)	0.88628 (15)	0.15023 (11)	0.0536 (6)
H10	1.1409	0.9166	0.1364	0.064*
C2	1.1644 (2)	1.29943 (15)	0.05976 (11)	0.0595 (6)
H2	1.1902	1.2655	0.0246	0.071*
C1	1.0499 (2)	1.27347 (13)	0.09516 (9)	0.0467 (5)
C7	1.0867 (3)	1.40218 (15)	0.16293 (11)	0.0608 (6)
H7	1.0604	1.4374	0.1973	0.073*
C22	1.4427 (3)	0.84197 (17)	−0.04630 (11)	0.0667 (7)
H22	1.3939	0.7953	−0.0657	0.080*
C27	0.5366 (2)	1.26970 (15)	0.23883 (11)	0.0546 (6)
C8	1.0115 (2)	1.32642 (13)	0.14618 (10)	0.0515 (5)
H8	0.9339	1.3108	0.1695	0.062*
N3	1.15792 (19)	1.00173 (12)	−0.02169 (9)	0.0609 (5)
H3	1.1793	1.0584	−0.0200	0.073*
C28	0.5385 (2)	1.20923 (16)	0.28849 (12)	0.0659 (7)
H28	0.5316	1.1474	0.2800	0.079*
N6	0.6510 (2)	1.18814 (14)	0.15343 (10)	0.0700 (6)
H6	0.6655	1.1360	0.1705	0.084*
C25	1.5885 (3)	0.9750 (2)	0.01361 (13)	0.0771 (8)
H25	1.6371	1.0200	0.0349	0.093*
C26	1.4546 (3)	0.99204 (16)	−0.00713 (12)	0.0654 (6)
H26	1.4150	1.0487	−0.0003	0.078*
C18	0.5259 (2)	1.23737 (17)	0.17096 (12)	0.0665 (7)
H18	0.5190	1.2910	0.1438	0.080*
C17	1.2367 (2)	0.94135 (14)	−0.06312 (10)	0.0515 (5)
H17	1.1894	0.8826	−0.0643	0.062*
C19	1.2379 (3)	0.97911 (17)	−0.12969 (12)	0.0685 (7)
H19A	1.1450	0.9886	−0.1437	0.103*
H19B	1.2829	0.9369	−0.1574	0.103*
H19C	1.2866	1.0358	−0.1302	0.103*
C5	1.2012 (3)	1.42479 (15)	0.12797 (13)	0.0647 (7)
C24	1.6486 (3)	0.8930 (2)	0.00299 (13)	0.0769 (8)
H24	1.7387	0.8823	0.0159	0.092*
C31	0.5579 (3)	1.3885 (2)	0.3163 (2)	0.0925 (10)
H31	0.5638	1.4501	0.3257	0.111*
C23	1.5758 (3)	0.8270 (2)	−0.02661 (13)	0.0766 (8)
H23	1.6164	0.7708	−0.0337	0.092*
C4	1.2394 (3)	1.37479 (17)	0.07648 (13)	0.0691 (7)
H4	1.3159	1.3917	0.0528	0.083*
C29	0.5502 (3)	1.2375 (2)	0.35034 (14)	0.0809 (8)
H29	0.5510	1.1951	0.3829	0.097*
C32	0.5464 (3)	1.36083 (17)	0.25330 (15)	0.0758 (8)
H32	0.5453	1.4039	0.2211	0.091*
C20	0.3998 (3)	1.1790 (2)	0.15957 (15)	0.0967 (10)
H20A	0.3969	1.1610	0.1160	0.145*
H20B	0.3185	1.2131	0.1696	0.145*
H20C	0.4042	1.1260	0.1859	0.145*
C30	0.5606 (3)	1.3271 (3)	0.36354 (15)	0.0865 (9)
H30	0.5695	1.3464	0.4052	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.1065 (5)	0.0540 (3)	0.0681 (4)	−0.0008 (4)	−0.0168 (4)	0.0070 (3)
Cl2	0.1104 (6)	0.0705 (5)	0.1283 (7)	−0.0315 (4)	−0.0333 (5)	−0.0013 (4)
O1	0.0634 (9)	0.0497 (8)	0.0625 (10)	−0.0088 (8)	0.0160 (8)	−0.0093 (7)
N2	0.0526 (10)	0.0440 (9)	0.0476 (10)	−0.0026 (9)	0.0097 (8)	−0.0061 (8)
C9	0.0368 (11)	0.0460 (11)	0.0410 (11)	0.0013 (9)	0.0029 (9)	−0.0042 (9)
N1	0.0480 (9)	0.0437 (9)	0.0450 (9)	−0.0011 (8)	0.0108 (8)	−0.0067 (7)
C12	0.0618 (15)	0.0495 (11)	0.0400 (12)	−0.0001 (11)	−0.0077 (11)	−0.0031 (9)
N4	0.0481 (10)	0.0448 (9)	0.0445 (10)	0.0062 (8)	0.0053 (8)	−0.0007 (8)
C14	0.0379 (11)	0.0606 (13)	0.0512 (13)	0.0000 (10)	0.0023 (10)	0.0009 (11)
N5	0.0456 (10)	0.0499 (10)	0.0454 (10)	0.0041 (8)	0.0043 (8)	−0.0036 (8)
C6	0.0336 (10)	0.0502 (12)	0.0429 (11)	0.0003 (9)	0.0001 (9)	−0.0064 (9)
C3	0.0518 (12)	0.0451 (11)	0.0360 (10)	0.0044 (10)	0.0010 (9)	−0.0016 (9)
C15	0.0469 (12)	0.0487 (12)	0.0436 (12)	0.0032 (10)	0.0036 (10)	−0.0060 (9)
C13	0.0486 (13)	0.0627 (14)	0.0512 (13)	−0.0106 (11)	0.0032 (11)	0.0041 (11)
O2	0.0657 (10)	0.0547 (9)	0.0594 (10)	0.0113 (8)	−0.0077 (8)	−0.0019 (8)
C16	0.0518 (13)	0.0567 (13)	0.0404 (12)	0.0115 (11)	−0.0057 (10)	−0.0122 (10)
C11	0.0486 (13)	0.0668 (15)	0.0627 (15)	0.0100 (12)	−0.0052 (11)	0.0035 (12)
C21	0.0541 (13)	0.0506 (13)	0.0411 (12)	−0.0066 (11)	0.0122 (10)	−0.0053 (10)
C10	0.0368 (12)	0.0618 (13)	0.0622 (15)	−0.0017 (11)	0.0019 (10)	0.0066 (11)
C2	0.0738 (16)	0.0514 (13)	0.0533 (14)	−0.0008 (12)	0.0101 (12)	0.0003 (11)
C1	0.0554 (13)	0.0428 (11)	0.0418 (11)	0.0040 (10)	−0.0035 (10)	0.0010 (9)
C7	0.0797 (18)	0.0516 (14)	0.0510 (14)	0.0029 (13)	−0.0144 (13)	−0.0077 (10)
C22	0.0734 (17)	0.0642 (15)	0.0624 (15)	0.0048 (14)	0.0004 (13)	−0.0212 (12)
C27	0.0377 (12)	0.0559 (13)	0.0701 (15)	0.0103 (10)	0.0135 (11)	0.0005 (11)
C8	0.0596 (13)	0.0488 (12)	0.0461 (12)	0.0036 (11)	−0.0039 (10)	−0.0023 (10)
N3	0.0633 (12)	0.0470 (10)	0.0723 (13)	−0.0071 (9)	0.0300 (10)	−0.0172 (9)
C28	0.0610 (16)	0.0641 (15)	0.0725 (17)	0.0094 (13)	0.0017 (13)	0.0014 (13)
N6	0.0674 (13)	0.0775 (14)	0.0650 (13)	0.0332 (11)	0.0242 (10)	0.0116 (11)
C25	0.0812 (19)	0.0749 (19)	0.0752 (19)	−0.0292 (16)	−0.0165 (15)	0.0101 (15)
C26	0.0781 (17)	0.0501 (13)	0.0680 (16)	−0.0139 (13)	−0.0007 (14)	−0.0001 (11)
C18	0.0570 (14)	0.0773 (16)	0.0650 (16)	0.0278 (13)	0.0072 (12)	0.0059 (12)
C17	0.0533 (13)	0.0464 (12)	0.0548 (14)	−0.0051 (10)	0.0149 (11)	−0.0131 (10)
C19	0.0650 (16)	0.0838 (17)	0.0566 (16)	0.0082 (14)	0.0041 (12)	−0.0089 (13)
C5	0.0740 (17)	0.0475 (13)	0.0727 (18)	−0.0043 (12)	−0.0169 (14)	0.0068 (13)
C24	0.0664 (17)	0.100 (2)	0.0646 (18)	−0.0030 (17)	−0.0029 (14)	0.0123 (16)
C31	0.0721 (19)	0.0754 (19)	0.130 (3)	0.0021 (16)	0.014 (2)	−0.036 (2)
C23	0.0709 (18)	0.0835 (19)	0.0755 (18)	0.0180 (16)	−0.0007 (14)	−0.0117 (15)
C4	0.0699 (16)	0.0597 (15)	0.0776 (19)	−0.0072 (13)	0.0082 (14)	0.0135 (13)
C29	0.0678 (17)	0.102 (2)	0.0729 (19)	0.0139 (17)	0.0053 (15)	0.0014 (17)
C32	0.0687 (17)	0.0626 (16)	0.096 (2)	0.0111 (13)	0.0218 (16)	0.0081 (15)
C20	0.0718 (18)	0.127 (3)	0.091 (2)	0.0209 (19)	−0.0122 (16)	−0.032 (2)
C30	0.0590 (16)	0.119 (3)	0.082 (2)	0.0147 (19)	0.0102 (15)	−0.026 (2)

Cl1—C12	1.737 (2)	C22—H22	0.9300
Cl2—C5	1.737 (3)	C27—C28	1.378 (3)
O1—C15	1.209 (2)	C27—C32	1.380 (3)
N2—C3	1.282 (2)	C27—C18	1.516 (3)
N2—N1	1.417 (2)	C8—H8	0.9300
C9—C14	1.376 (3)	N3—C17	1.465 (3)
C9—C10	1.379 (3)	N3—H3	0.8600
C9—C6	1.485 (3)	C28—C29	1.378 (4)
N1—C6	1.396 (2)	C28—H28	0.9300
N1—C15	1.415 (2)	N6—C18	1.463 (3)
C12—C11	1.371 (3)	N6—H6	0.8600
C12—C13	1.373 (3)	C25—C24	1.359 (4)
N4—C3	1.407 (3)	C25—C26	1.396 (4)
N4—C16	1.408 (3)	C25—H25	0.9300
N4—N5	1.429 (2)	C26—H26	0.9300
C14—C13	1.377 (3)	C18—C20	1.516 (4)
C14—H14	0.9300	C18—H18	0.9800
N5—C6	1.285 (2)	C17—C19	1.514 (3)
C3—C1	1.482 (3)	C17—H17	0.9800
C15—N3	1.332 (3)	C19—H19A	0.9600
C13—H13	0.9300	C19—H19B	0.9600
O2—C16	1.221 (2)	C19—H19C	0.9600
C16—N6	1.332 (3)	C5—C4	1.366 (4)
C11—C10	1.376 (3)	C24—C23	1.355 (4)
C11—H11	0.9300	C24—H24	0.9300
C21—C26	1.377 (3)	C31—C30	1.348 (4)
C21—C22	1.380 (3)	C31—C32	1.399 (4)
C21—C17	1.517 (3)	C31—H31	0.9300
C10—H10	0.9300	C23—H23	0.9300
C2—C4	1.374 (3)	C4—H4	0.9300
C2—C1	1.395 (3)	C29—C30	1.352 (4)
C2—H2	0.9300	C29—H29	0.9300
C1—C8	1.383 (3)	C32—H32	0.9300
C7—C5	1.377 (4)	C20—H20A	0.9600
C7—C8	1.380 (3)	C20—H20B	0.9600
C7—H7	0.9300	C20—H20C	0.9600
C22—C23	1.376 (4)	C30—H30	0.9300
C3—N2—N1	112.04 (16)	C17—N3—H3	119.1
C14—C9—C10	118.89 (18)	C27—C28—C29	122.0 (2)
C14—C9—C6	120.35 (18)	C27—C28—H28	119.0
C10—C9—C6	120.69 (18)	C29—C28—H28	119.0
C6—N1—C15	122.19 (16)	C16—N6—C18	123.7 (2)
C6—N1—N2	114.56 (15)	C16—N6—H6	118.1
C15—N1—N2	117.23 (15)	C18—N6—H6	118.1
C11—C12—C13	120.78 (19)	C24—C25—C26	120.5 (3)
C11—C12—Cl1	118.95 (17)	C24—C25—H25	119.7
C13—C12—Cl1	120.26 (18)	C26—C25—H25	119.7
C3—N4—C16	125.43 (17)	C21—C26—C25	120.3 (2)
C3—N4—N5	114.03 (15)	C21—C26—H26	119.8
C16—N4—N5	116.47 (16)	C25—C26—H26	119.8
C9—C14—C13	120.7 (2)	N6—C18—C20	110.5 (2)
C9—C14—H14	119.7	N6—C18—C27	109.80 (19)
C13—C14—H14	119.7	C20—C18—C27	112.6 (2)
C6—N5—N4	111.37 (16)	N6—C18—H18	107.9
N5—C6—N1	118.85 (17)	C20—C18—H18	107.9
N5—C6—C9	118.05 (18)	C27—C18—H18	107.9
N1—C6—C9	122.67 (16)	N3—C17—C19	109.74 (19)
N2—C3—N4	118.31 (17)	N3—C17—C21	111.32 (18)
N2—C3—C1	117.47 (18)	C19—C17—C21	112.34 (18)
N4—C3—C1	123.57 (18)	N3—C17—H17	107.7
O1—C15—N3	125.77 (19)	C19—C17—H17	107.7
O1—C15—N1	120.04 (18)	C21—C17—H17	107.7
N3—C15—N1	114.14 (18)	C17—C19—H19A	109.5
C12—C13—C14	119.5 (2)	C17—C19—H19B	109.5
C12—C13—H13	120.3	H19A—C19—H19B	109.5
C14—C13—H13	120.3	C17—C19—H19C	109.5
O2—C16—N6	126.6 (2)	H19A—C19—H19C	109.5
O2—C16—N4	120.1 (2)	H19B—C19—H19C	109.5
N6—C16—N4	113.33 (19)	C4—C5—C7	121.2 (2)
C12—C11—C10	119.2 (2)	C4—C5—Cl2	119.9 (2)
C12—C11—H11	120.4	C7—C5—Cl2	119.0 (2)
C10—C11—H11	120.4	C23—C24—C25	119.3 (3)
C26—C21—C22	118.0 (2)	C23—C24—H24	120.4
C26—C21—C17	122.4 (2)	C25—C24—H24	120.4
C22—C21—C17	119.5 (2)	C30—C31—C32	120.8 (3)
C11—C10—C9	121.0 (2)	C30—C31—H31	119.6
C11—C10—H10	119.5	C32—C31—H31	119.6
C9—C10—H10	119.5	C24—C23—C22	121.0 (3)
C4—C2—C1	120.4 (2)	C24—C23—H23	119.5
C4—C2—H2	119.8	C22—C23—H23	119.5
C1—C2—H2	119.8	C5—C4—C2	119.8 (2)
C8—C1—C2	118.7 (2)	C5—C4—H4	120.1
C8—C1—C3	122.51 (19)	C2—C4—H4	120.1
C2—C1—C3	118.25 (19)	C30—C29—C28	119.8 (3)
C5—C7—C8	119.0 (2)	C30—C29—H29	120.1
C5—C7—H7	120.5	C28—C29—H29	120.1
C8—C7—H7	120.5	C27—C32—C31	120.0 (3)
C23—C22—C21	120.8 (2)	C27—C32—H32	120.0
C23—C22—H22	119.6	C31—C32—H32	120.0
C21—C22—H22	119.6	C18—C20—H20A	109.5
C28—C27—C32	117.3 (2)	C18—C20—H20B	109.5
C28—C27—C18	121.4 (2)	H20A—C20—H20B	109.5
C32—C27—C18	121.3 (2)	C18—C20—H20C	109.5
C7—C8—C1	120.9 (2)	H20A—C20—H20C	109.5
C7—C8—H8	119.6	H20B—C20—H20C	109.5
C1—C8—H8	119.6	C31—C30—C29	120.0 (3)
C15—N3—C17	121.72 (18)	C31—C30—H30	120.0
C15—N3—H3	119.1	C29—C30—H30	120.0
C3—N2—N1—C6	−43.9 (2)	N2—C3—C1—C2	25.8 (3)
C3—N2—N1—C15	162.73 (18)	N4—C3—C1—C2	−163.65 (19)
C10—C9—C14—C13	−0.9 (3)	C26—C21—C22—C23	−1.9 (3)
C6—C9—C14—C13	−177.96 (19)	C17—C21—C22—C23	176.6 (2)
C3—N4—N5—C6	−44.5 (2)	C5—C7—C8—C1	0.1 (3)
C16—N4—N5—C6	156.90 (17)	C2—C1—C8—C7	−1.7 (3)
N4—N5—C6—N1	3.2 (2)	C3—C1—C8—C7	169.61 (19)
N4—N5—C6—C9	175.90 (16)	O1—C15—N3—C17	−7.2 (4)
C15—N1—C6—N5	−166.24 (18)	N1—C15—N3—C17	175.42 (19)
N2—N1—C6—N5	41.9 (2)	C32—C27—C28—C29	−0.3 (4)
C15—N1—C6—C9	21.4 (3)	C18—C27—C28—C29	179.0 (2)
N2—N1—C6—C9	−130.45 (18)	O2—C16—N6—C18	−1.1 (4)
C14—C9—C6—N5	50.0 (3)	N4—C16—N6—C18	−178.7 (2)
C10—C9—C6—N5	−127.1 (2)	C22—C21—C26—C25	0.7 (3)
C14—C9—C6—N1	−137.6 (2)	C17—C21—C26—C25	−177.9 (2)
C10—C9—C6—N1	45.3 (3)	C24—C25—C26—C21	1.1 (4)
N1—N2—C3—N4	2.3 (2)	C16—N6—C18—C20	124.9 (3)
N1—N2—C3—C1	173.40 (16)	C16—N6—C18—C27	−110.3 (3)
C16—N4—C3—N2	−161.03 (18)	C28—C27—C18—N6	−67.0 (3)
N5—N4—C3—N2	42.6 (2)	C32—C27—C18—N6	112.3 (3)
C16—N4—C3—C1	28.5 (3)	C28—C27—C18—C20	56.6 (3)
N5—N4—C3—C1	−127.88 (18)	C32—C27—C18—C20	−124.1 (3)
C6—N1—C15—O1	24.2 (3)	C15—N3—C17—C19	126.1 (2)
N2—N1—C15—O1	175.37 (18)	C15—N3—C17—C21	−108.9 (2)
C6—N1—C15—N3	−158.24 (18)	C26—C21—C17—N3	−36.0 (3)
N2—N1—C15—N3	−7.0 (3)	C22—C21—C17—N3	145.54 (19)
C11—C12—C13—C14	0.5 (3)	C26—C21—C17—C19	87.6 (2)
Cl1—C12—C13—C14	179.46 (16)	C22—C21—C17—C19	−90.9 (2)
C9—C14—C13—C12	0.4 (3)	C8—C7—C5—C4	1.4 (4)
C3—N4—C16—O2	27.1 (3)	C8—C7—C5—Cl2	−179.52 (17)
N5—N4—C16—O2	−177.10 (18)	C26—C25—C24—C23	−1.7 (4)
C3—N4—C16—N6	−155.15 (19)	C25—C24—C23—C22	0.4 (4)
N5—N4—C16—N6	0.7 (2)	C21—C22—C23—C24	1.5 (4)
C13—C12—C11—C10	−0.9 (3)	C7—C5—C4—C2	−1.4 (4)
Cl1—C12—C11—C10	−179.83 (17)	Cl2—C5—C4—C2	179.60 (18)
C12—C11—C10—C9	0.4 (3)	C1—C2—C4—C5	−0.3 (4)
C14—C9—C10—C11	0.5 (3)	C27—C28—C29—C30	−0.1 (4)
C6—C9—C10—C11	177.59 (19)	C28—C27—C32—C31	0.1 (4)
C4—C2—C1—C8	1.7 (3)	C18—C27—C32—C31	−179.2 (2)
C4—C2—C1—C3	−169.9 (2)	C30—C31—C32—C27	0.4 (4)
N2—C3—C1—C8	−145.6 (2)	C32—C31—C30—C29	−0.9 (5)
N4—C3—C1—C8	25.0 (3)	C28—C29—C30—C31	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.86	2.21	2.613 (2)	109
N6—H6···N5	0.86	2.13	2.573 (2)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2	0.86	2.21	2.613 (2)	109
N6—H6⋯N5	0.86	2.13	2.573 (2)	112