2,9-Dimethyl-7-phenyl-N-(4-methyl-phen-yl)dibenzo[b,h][1,6]naphthyridin-6-amine.

The title compound, C(31)H(25)N(3), was synthesized from 6,4',4''-trimethyl-2,4-bis-(N-phenyl-amino)-quinoline and is the first structural example containing a phenyl and phenyl-amino fragment attached to a fused dibenzo[1,6]naphthyridine moiety. The fused tetra-cyclic ring system is essentially planar [r.m.s. deviation = 0.08 (3) Å]. The phenyl ring and the phenyl-amino group are inclined by 82.68 (6) and 35.31 (5)°, respectively, to the mean plane of the fused tetra-cyclic ring system. A weak intra-molecular N-H⋯π(arene) inter-action may in part influence the conformation of the mol-ecule. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯N hydrogen bonds into centrosymmetric dimers. Additional stabilization is provided by weak C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.834 (2) and 3.898 (1) Å].

Related literature

For the biological activity of [1,6]naphthyridine derivatives, see: Ruchelman et al. (2003 ▶, 2005 ▶); Hinschberger et al. (2003 ▶); Bedard et al. (2000 ▶); Feng et al. (2008 ▶). For the synthesis of the title compound, see: Manoj & Rajendra Prasad (2009 ▶). For the crystal structures of other [1,6]naphthrydine derivatives, see: Peng et al. (2009 ▶); Sivakumar et al. (2003 ▶); Seebacher et al. (2010 ▶); Vennila et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C31H25N3

M = 439.54

Monoclinic,

a = 11.9390 (4) Å

b = 10.5595 (4) Å

c = 19.6084 (7) Å

β = 107.369 (2)°

V = 2359.31 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.982, T max = 0.986

17909 measured reflections

2938 independent reflections

2197 reflections with I > 2σ(I)

R int = 0.037

θmax = 22.1°

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.132

S = 1.07

2938 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976) ▶; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051196/lh5177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051196/lh5177Isup2.hkl

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

C31H25N3	F(000) = 928
Mr = 439.54	Dx = 1.237 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2938 reflections
a = 11.9390 (4) Å	θ = 2.2–21.2°
b = 10.5595 (4) Å	µ = 0.07 mm−1
c = 19.6084 (7) Å	T = 293 K
β = 107.369 (2)°	Prismatic, yellow
V = 2359.31 (15) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	2938 independent reflections
Radiation source: fine-focus sealed tube	2197 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω and φ scans	θmax = 22.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.982, Tmax = 0.986	k = −11→11
17909 measured reflections	l = −20→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.4411P] where P = (Fo2 + 2Fc2)/3
2938 reflections	(Δ/σ)max = 0.034
310 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 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
C2	0.21879 (18)	0.4613 (2)	0.03581 (11)	0.0434 (6)
N1	0.32355 (16)	0.27439 (18)	0.01274 (10)	0.0508 (5)
N2	0.12176 (16)	0.44039 (18)	0.12785 (10)	0.0529 (5)
C3	0.18596 (18)	0.3921 (2)	0.08942 (12)	0.0448 (6)
C4	0.22420 (18)	0.2617 (2)	0.10461 (12)	0.0448 (6)
C12	0.08099 (19)	0.5597 (2)	0.11381 (12)	0.0511 (6)
N3	0.32400 (17)	0.45075 (18)	−0.05365 (10)	0.0569 (6)
H3	0.3031	0.5288	−0.0607	0.068*
C11	0.10670 (18)	0.6366 (2)	0.06154 (12)	0.0461 (6)
C5	0.29150 (19)	0.2088 (2)	0.06518 (12)	0.0473 (6)
C1	0.29049 (18)	0.3908 (2)	−0.00132 (12)	0.0459 (6)
C10	0.18035 (18)	0.5874 (2)	0.02346 (11)	0.0448 (6)
C9	0.19467 (19)	0.1887 (2)	0.15606 (12)	0.0512 (6)
H9	0.1499	0.2250	0.1824	0.061*
C8	0.2296 (2)	0.0654 (2)	0.16883 (12)	0.0523 (6)
C17	0.21691 (19)	0.6767 (2)	−0.02498 (13)	0.0464 (6)
C23	0.38787 (19)	0.4030 (2)	−0.09768 (12)	0.0480 (6)
C16	0.0570 (2)	0.7604 (2)	0.05065 (13)	0.0546 (6)
H16	0.0741	0.8128	0.0169	0.066*
C6	0.3278 (2)	0.0832 (2)	0.07839 (13)	0.0592 (7)
H6	0.3736	0.0465	0.0528	0.071*
C14	−0.0376 (2)	0.7257 (3)	0.13967 (14)	0.0659 (7)
H14	−0.0858	0.7554	0.1657	0.079*
C13	0.0083 (2)	0.6078 (3)	0.15287 (14)	0.0666 (7)
H13	−0.0082	0.5581	0.1879	0.080*
C7	0.2968 (2)	0.0136 (2)	0.12858 (13)	0.0604 (7)
H7	0.3210	−0.0702	0.1361	0.073*
C24	0.4578 (2)	0.4875 (2)	−0.11974 (13)	0.0548 (6)
H24	0.4660	0.5699	−0.1022	0.066*
C15	−0.0144 (2)	0.8045 (2)	0.08782 (14)	0.0575 (7)
C29	0.1979 (2)	−0.0121 (3)	0.22479 (14)	0.0678 (8)
H29A	0.1430	0.0340	0.2424	0.102*
H29B	0.2674	−0.0292	0.2635	0.102*
H29C	0.1632	−0.0906	0.2042	0.102*
C22	0.1465 (2)	0.7020 (2)	−0.09377 (14)	0.0617 (7)
H22	0.0736	0.6633	−0.1112	0.074*
C28	0.3782 (2)	0.2810 (2)	−0.12414 (13)	0.0571 (7)
H28	0.3323	0.2220	−0.1094	0.069*
C27	0.4362 (2)	0.2465 (3)	−0.17227 (13)	0.0632 (7)
H27	0.4281	0.1641	−0.1898	0.076*
C26	0.5057 (2)	0.3298 (3)	−0.19527 (13)	0.0617 (7)
C25	0.5157 (2)	0.4509 (3)	−0.16770 (13)	0.0609 (7)
H25	0.5628	0.5093	−0.1818	0.073*
C18	0.3242 (2)	0.7371 (2)	−0.00024 (15)	0.0591 (7)
H18	0.3714	0.7220	0.0462	0.071*
C21	0.1851 (3)	0.7849 (3)	−0.13643 (16)	0.0780 (9)
H21	0.1380	0.8018	−0.1827	0.094*
C30	−0.0682 (2)	0.9343 (2)	0.07514 (16)	0.0744 (8)
H30A	−0.0115	0.9959	0.0999	0.112*
H30B	−0.1353	0.9375	0.0925	0.112*
H30C	−0.0921	0.9525	0.0249	0.112*
C20	0.2927 (3)	0.8426 (3)	−0.1109 (2)	0.0818 (10)
H20	0.3183	0.8980	−0.1399	0.098*
C19	0.3623 (3)	0.8190 (3)	−0.04288 (19)	0.0752 (8)
H19	0.4351	0.8582	−0.0257	0.090*
C31	0.5664 (3)	0.2936 (3)	−0.24940 (15)	0.0941 (11)
H31A	0.5255	0.3305	−0.2948	0.141*
H31B	0.5666	0.2031	−0.2539	0.141*
H31C	0.6457	0.3242	−0.2341	0.141*

	U11	U22	U33	U12	U13	U23
C2	0.0396 (12)	0.0431 (14)	0.0481 (14)	0.0009 (10)	0.0139 (11)	−0.0022 (11)
N1	0.0549 (12)	0.0442 (13)	0.0578 (13)	0.0076 (9)	0.0240 (10)	0.0019 (10)
N2	0.0570 (12)	0.0496 (13)	0.0591 (13)	0.0049 (10)	0.0277 (10)	0.0003 (10)
C3	0.0415 (13)	0.0463 (14)	0.0475 (14)	0.0003 (10)	0.0149 (11)	−0.0041 (11)
C4	0.0427 (13)	0.0444 (14)	0.0461 (14)	−0.0006 (10)	0.0115 (11)	−0.0010 (11)
C12	0.0506 (14)	0.0493 (16)	0.0578 (15)	0.0032 (12)	0.0228 (12)	−0.0040 (13)
N3	0.0722 (14)	0.0440 (12)	0.0677 (14)	0.0125 (10)	0.0410 (12)	0.0060 (10)
C11	0.0436 (13)	0.0410 (14)	0.0549 (15)	0.0023 (10)	0.0165 (11)	−0.0046 (11)
C5	0.0470 (13)	0.0435 (15)	0.0508 (14)	0.0027 (11)	0.0138 (11)	−0.0007 (12)
C1	0.0434 (13)	0.0448 (15)	0.0507 (15)	0.0025 (11)	0.0158 (11)	−0.0020 (12)
C10	0.0422 (13)	0.0435 (15)	0.0485 (14)	0.0001 (10)	0.0133 (11)	−0.0023 (11)
C9	0.0489 (14)	0.0526 (17)	0.0526 (15)	0.0011 (11)	0.0158 (12)	−0.0003 (12)
C8	0.0520 (14)	0.0495 (16)	0.0509 (15)	−0.0005 (12)	0.0088 (12)	0.0042 (12)
C17	0.0485 (14)	0.0387 (14)	0.0565 (16)	0.0069 (11)	0.0225 (12)	0.0006 (12)
C23	0.0508 (14)	0.0473 (15)	0.0492 (14)	0.0090 (11)	0.0198 (12)	0.0027 (12)
C16	0.0553 (14)	0.0475 (15)	0.0620 (16)	0.0045 (11)	0.0189 (13)	−0.0021 (12)
C6	0.0664 (16)	0.0510 (17)	0.0650 (17)	0.0116 (13)	0.0266 (14)	0.0006 (13)
C14	0.0642 (16)	0.0645 (19)	0.080 (2)	0.0080 (14)	0.0376 (15)	−0.0138 (15)
C13	0.0743 (18)	0.0638 (19)	0.0756 (18)	0.0079 (14)	0.0437 (15)	−0.0024 (15)
C7	0.0693 (17)	0.0465 (16)	0.0641 (18)	0.0089 (12)	0.0178 (14)	0.0072 (13)
C24	0.0616 (15)	0.0505 (16)	0.0568 (16)	0.0037 (12)	0.0244 (13)	0.0030 (12)
C15	0.0507 (14)	0.0545 (16)	0.0683 (17)	0.0057 (12)	0.0193 (13)	−0.0115 (14)
C29	0.0722 (18)	0.0643 (18)	0.0665 (18)	−0.0023 (13)	0.0200 (14)	0.0124 (14)
C22	0.0666 (16)	0.0567 (17)	0.0641 (18)	0.0094 (13)	0.0230 (15)	0.0042 (14)
C28	0.0601 (15)	0.0553 (17)	0.0623 (16)	0.0010 (12)	0.0280 (13)	−0.0026 (13)
C27	0.0730 (17)	0.0601 (17)	0.0597 (17)	0.0098 (14)	0.0248 (14)	−0.0055 (13)
C26	0.0681 (17)	0.071 (2)	0.0508 (16)	0.0211 (14)	0.0254 (13)	0.0070 (14)
C25	0.0569 (15)	0.073 (2)	0.0594 (16)	0.0070 (13)	0.0274 (13)	0.0154 (15)
C18	0.0631 (16)	0.0503 (16)	0.0694 (17)	−0.0022 (13)	0.0282 (14)	−0.0012 (13)
C21	0.111 (3)	0.070 (2)	0.0632 (19)	0.0262 (19)	0.0413 (18)	0.0143 (16)
C30	0.0693 (17)	0.0624 (18)	0.091 (2)	0.0197 (14)	0.0233 (15)	−0.0106 (16)
C20	0.118 (3)	0.0528 (19)	0.105 (3)	0.0048 (18)	0.079 (2)	0.0082 (18)
C19	0.084 (2)	0.0567 (19)	0.101 (3)	−0.0073 (15)	0.052 (2)	−0.0060 (18)
C31	0.115 (3)	0.111 (3)	0.076 (2)	0.033 (2)	0.058 (2)	0.0119 (19)

C2—C10	1.406 (3)	C14—C15	1.403 (3)
C2—C3	1.428 (3)	C14—H14	0.9300
C2—C1	1.480 (3)	C13—H13	0.9300
N1—C1	1.295 (3)	C7—H7	0.9300
N1—C5	1.385 (3)	C24—C25	1.379 (3)
N2—C3	1.327 (3)	C24—H24	0.9300
N2—C12	1.349 (3)	C15—C30	1.503 (3)
C3—C4	1.453 (3)	C29—H29A	0.9600
C4—C5	1.388 (3)	C29—H29B	0.9600
C4—C9	1.396 (3)	C29—H29C	0.9600
C12—C11	1.411 (3)	C22—C21	1.381 (4)
C12—C13	1.412 (3)	C22—H22	0.9300
N3—C1	1.364 (3)	C28—C27	1.376 (3)
N3—C23	1.405 (3)	C28—H28	0.9300
N3—H3	0.8600	C27—C26	1.374 (4)
C11—C10	1.412 (3)	C27—H27	0.9300
C11—C16	1.424 (3)	C26—C25	1.380 (4)
C5—C6	1.396 (3)	C26—C31	1.502 (3)
C10—C17	1.493 (3)	C25—H25	0.9300
C9—C8	1.368 (3)	C18—C19	1.371 (4)
C9—H9	0.9300	C18—H18	0.9300
C8—C7	1.394 (3)	C21—C20	1.374 (4)
C8—C29	1.505 (3)	C21—H21	0.9300
C17—C18	1.383 (3)	C30—H30A	0.9600
C17—C22	1.386 (3)	C30—H30B	0.9600
C23—C24	1.377 (3)	C30—H30C	0.9600
C23—C28	1.381 (3)	C20—C19	1.367 (4)
C16—C15	1.359 (3)	C20—H20	0.9300
C16—H16	0.9300	C19—H19	0.9300
C6—C7	1.365 (3)	C31—H31A	0.9600
C6—H6	0.9300	C31—H31B	0.9600
C14—C13	1.354 (3)	C31—H31C	0.9600
C10—C2—C3	117.67 (19)	C6—C7—H7	119.2
C10—C2—C1	126.8 (2)	C8—C7—H7	119.2
C3—C2—C1	115.5 (2)	C23—C24—C25	120.4 (2)
C1—N1—C5	119.88 (18)	C23—C24—H24	119.8
C3—N2—C12	118.52 (19)	C25—C24—H24	119.8
N2—C3—C2	123.6 (2)	C16—C15—C14	118.5 (2)
N2—C3—C4	116.57 (19)	C16—C15—C30	121.9 (2)
C2—C3—C4	119.82 (18)	C14—C15—C30	119.6 (2)
C5—C4—C9	119.6 (2)	C8—C29—H29A	109.5
C5—C4—C3	117.8 (2)	C8—C29—H29B	109.5
C9—C4—C3	122.7 (2)	H29A—C29—H29B	109.5
N2—C12—C11	122.84 (19)	C8—C29—H29C	109.5
N2—C12—C13	117.9 (2)	H29A—C29—H29C	109.5
C11—C12—C13	119.3 (2)	H29B—C29—H29C	109.5
C1—N3—C23	129.1 (2)	C21—C22—C17	119.8 (3)
C1—N3—H3	115.4	C21—C22—H22	120.1
C23—N3—H3	115.4	C17—C22—H22	120.1
C10—C11—C12	118.5 (2)	C27—C28—C23	120.1 (2)
C10—C11—C16	123.7 (2)	C27—C28—H28	119.9
C12—C11—C16	117.8 (2)	C23—C28—H28	119.9
N1—C5—C4	123.1 (2)	C28—C27—C26	122.2 (3)
N1—C5—C6	118.3 (2)	C28—C27—H27	118.9
C4—C5—C6	118.6 (2)	C26—C27—H27	118.9
N1—C1—N3	117.50 (19)	C27—C26—C25	117.1 (2)
N1—C1—C2	123.9 (2)	C27—C26—C31	122.4 (3)
N3—C1—C2	118.6 (2)	C25—C26—C31	120.6 (3)
C2—C10—C11	118.7 (2)	C24—C25—C26	121.7 (2)
C2—C10—C17	124.41 (19)	C24—C25—H25	119.2
C11—C10—C17	116.81 (19)	C26—C25—H25	119.2
C8—C9—C4	122.0 (2)	C19—C18—C17	121.2 (3)
C8—C9—H9	119.0	C19—C18—H18	119.4
C4—C9—H9	119.0	C17—C18—H18	119.4
C9—C8—C7	117.7 (2)	C20—C21—C22	120.3 (3)
C9—C8—C29	121.5 (2)	C20—C21—H21	119.9
C7—C8—C29	120.8 (2)	C22—C21—H21	119.9
C18—C17—C22	118.8 (2)	C15—C30—H30A	109.5
C18—C17—C10	119.0 (2)	C15—C30—H30B	109.5
C22—C17—C10	122.3 (2)	H30A—C30—H30B	109.5
C24—C23—C28	118.5 (2)	C15—C30—H30C	109.5
C24—C23—N3	116.8 (2)	H30A—C30—H30C	109.5
C28—C23—N3	124.4 (2)	H30B—C30—H30C	109.5
C15—C16—C11	122.3 (2)	C19—C20—C21	120.3 (3)
C15—C16—H16	118.9	C19—C20—H20	119.8
C11—C16—H16	118.9	C21—C20—H20	119.8
C7—C6—C5	120.6 (2)	C20—C19—C18	119.6 (3)
C7—C6—H6	119.7	C20—C19—H19	120.2
C5—C6—H6	119.7	C18—C19—H19	120.2
C13—C14—C15	121.8 (2)	C26—C31—H31A	109.5
C13—C14—H14	119.1	C26—C31—H31B	109.5
C15—C14—H14	119.1	H31A—C31—H31B	109.5
C14—C13—C12	120.4 (2)	C26—C31—H31C	109.5
C14—C13—H13	119.8	H31A—C31—H31C	109.5
C12—C13—H13	119.8	H31B—C31—H31C	109.5
C6—C7—C8	121.6 (2)
C12—N2—C3—C2	2.8 (3)	C4—C9—C8—C7	0.2 (3)
C12—N2—C3—C4	−177.8 (2)	C4—C9—C8—C29	179.5 (2)
C10—C2—C3—N2	−0.1 (3)	C2—C10—C17—C18	−80.6 (3)
C1—C2—C3—N2	−179.91 (19)	C11—C10—C17—C18	96.2 (3)
C10—C2—C3—C4	−179.53 (19)	C2—C10—C17—C22	100.0 (3)
C1—C2—C3—C4	0.6 (3)	C11—C10—C17—C22	−83.2 (3)
N2—C3—C4—C5	180.0 (2)	C1—N3—C23—C24	−149.1 (2)
C2—C3—C4—C5	−0.5 (3)	C1—N3—C23—C28	36.0 (4)
N2—C3—C4—C9	0.8 (3)	C10—C11—C16—C15	179.4 (2)
C2—C3—C4—C9	−179.7 (2)	C12—C11—C16—C15	−1.0 (3)
C3—N2—C12—C11	−2.0 (3)	N1—C5—C6—C7	−178.8 (2)
C3—N2—C12—C13	177.1 (2)	C4—C5—C6—C7	0.6 (4)
N2—C12—C11—C10	−1.4 (3)	C15—C14—C13—C12	−0.5 (4)
C13—C12—C11—C10	179.5 (2)	N2—C12—C13—C14	−178.3 (2)
N2—C12—C11—C16	179.0 (2)	C11—C12—C13—C14	0.9 (4)
C13—C12—C11—C16	−0.1 (3)	C5—C6—C7—C8	−0.9 (4)
C1—N1—C5—C4	0.0 (3)	C9—C8—C7—C6	0.4 (4)
C1—N1—C5—C6	179.4 (2)	C29—C8—C7—C6	−178.9 (2)
C9—C4—C5—N1	179.4 (2)	C28—C23—C24—C25	0.6 (3)
C3—C4—C5—N1	0.2 (3)	N3—C23—C24—C25	−174.7 (2)
C9—C4—C5—C6	0.0 (3)	C11—C16—C15—C14	1.4 (4)
C3—C4—C5—C6	−179.2 (2)	C11—C16—C15—C30	−178.9 (2)
C5—N1—C1—N3	−179.7 (2)	C13—C14—C15—C16	−0.6 (4)
C5—N1—C1—C2	0.1 (3)	C13—C14—C15—C30	179.7 (2)
C23—N3—C1—N1	2.3 (4)	C18—C17—C22—C21	1.0 (3)
C23—N3—C1—C2	−177.5 (2)	C10—C17—C22—C21	−179.6 (2)
C10—C2—C1—N1	179.7 (2)	C24—C23—C28—C27	−0.9 (4)
C3—C2—C1—N1	−0.5 (3)	N3—C23—C28—C27	173.9 (2)
C10—C2—C1—N3	−0.4 (3)	C23—C28—C27—C26	0.5 (4)
C3—C2—C1—N3	179.37 (19)	C28—C27—C26—C25	0.3 (4)
C3—C2—C10—C11	−3.4 (3)	C28—C27—C26—C31	−178.2 (2)
C1—C2—C10—C11	176.4 (2)	C23—C24—C25—C26	0.2 (4)
C3—C2—C10—C17	173.4 (2)	C27—C26—C25—C24	−0.7 (4)
C1—C2—C10—C17	−6.8 (4)	C31—C26—C25—C24	177.8 (2)
C12—C11—C10—C2	4.1 (3)	C22—C17—C18—C19	−1.2 (4)
C16—C11—C10—C2	−176.3 (2)	C10—C17—C18—C19	179.3 (2)
C12—C11—C10—C17	−172.9 (2)	C17—C22—C21—C20	−0.2 (4)
C16—C11—C10—C17	6.6 (3)	C22—C21—C20—C19	−0.3 (4)
C5—C4—C9—C8	−0.4 (3)	C21—C20—C19—C18	0.1 (4)
C3—C4—C9—C8	178.8 (2)	C17—C18—C19—C20	0.7 (4)

Cg1 and Cg2 are the centroids of the C17–C22 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cg1	0.86	2.51	3.364 (3)	174
C18—H18···Cg2i	0.93	2.62	3.495 (3)	156
C29—H29B···Cg2ii	0.96	2.90	3.622 (3)	133
C22—H22···N2iii	0.93	2.51	3.419 (3)	166
C28—H28···N1	0.93	2.49	2.946 (3)	110

Cg(I)	Cg(J)	Centroid-to-Centroid
Cg(2)	Cg(4i)	3.834 (2)
Cg(3)	Cg(3i)	3.898 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C17–C22 and C23–C28 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cg1	0.86	2.51	3.364 (3)	174
C18—H18⋯Cg2i	0.93	2.62	3.495 (3)	156
C29—H29B⋯Cg2ii	0.96	2.90	3.622 (3)	133
C22—H22⋯N2iii	0.93	2.51	3.419 (3)	166

Symmetry codes: (i) ; (ii) ; (iii) .