7-(4-Meth-oxy-phen-yl)-4,9-dimethyl-N-(4-methyl-phen-yl)-5,12-diaza-tetra-phen-6-amine.

In the title compound, C(32)H(27)N(3)O, the fused tetra-cycilc ring system is essentially planar [r.m.s. deviation = 0.07 (7) Å]. An intra-molecular N-H⋯π(arene) inter-action and a weak intra-molecular C-H⋯N hydrogen bond may influence the mol-ecular conformation. In the crystal, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric dimers, forming R(2) (2)(14) motifs. In addition, weak π-π stacking inter-actions with centroid-centroid distances in the range 3.578 (1)-3.739 (1) Å provide further stabilization.

Related literature

For the biological activity of naphthyridine derivatives, see: Gopalsamy et al. (2007 ▶); Kim et al. (2009 ▶); n class="Chemical">Nittoli et al. (2010 ▶); Bedard et al. (2000 ▶). For the structures of related naphthrydine derivatives, see: Peng et al. (2009 ▶); Seebacher et al . (2010) ▶; Vennila et al. (2010a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C32H27N3O

M = 469.57

Monoclinic,

a = 8.3816 (6) Å

b = 23.1651 (13) Å

c = 12.8548 (7) Å

β = 91.171 (3)°

V = 2495.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.29 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004) T min = 0.978, T max = 0.983

24206 measured reflections

6239 independent reflections

3904 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.181

S = 0.95

6239 reflections

329 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006209/lh5193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006209/lh5193Isup2.hkl

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

C32H27N3O	F(000) = 992
Mr = 469.57	Dx = 1.250 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6327 reflections
a = 8.3816 (6) Å	θ = 1.8–28.5°
b = 23.1651 (13) Å	µ = 0.08 mm−1
c = 12.8548 (7) Å	T = 293 K
β = 91.171 (3)°	Block, yellow
V = 2495.4 (3) Å3	0.29 × 0.24 × 0.23 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	6239 independent reflections
Radiation source: fine-focus sealed tube	3904 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 28.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.978, Tmax = 0.983	k = −29→30
24206 measured reflections	l = −17→16

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0992P)2 + 0.5542P] where P = (Fo2 + 2Fc2)/3
6239 reflections	(Δ/σ)max = 0.001
329 parameters	Δρmax = 0.27 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
C11	0.27001 (18)	0.47982 (7)	0.01559 (12)	0.0415 (4)
N2	0.38310 (17)	0.54757 (6)	0.14162 (11)	0.0481 (3)
C9	0.44758 (19)	0.50366 (7)	0.19420 (12)	0.0437 (4)
C8	0.43129 (19)	0.44464 (7)	0.16148 (12)	0.0419 (4)
C17	0.29497 (18)	0.37335 (7)	0.03664 (12)	0.0416 (4)
C6	0.6097 (2)	0.47172 (8)	0.34423 (13)	0.0506 (4)
C10	0.29963 (19)	0.53681 (7)	0.05320 (13)	0.0452 (4)
C12	0.33652 (18)	0.43309 (6)	0.07278 (12)	0.0411 (4)
C7	0.52499 (19)	0.40261 (7)	0.22420 (12)	0.0445 (4)
C14	0.11930 (19)	0.51950 (8)	−0.13214 (13)	0.0488 (4)
N1	0.60278 (17)	0.41521 (6)	0.30973 (11)	0.0509 (4)
C13	0.1761 (2)	0.47325 (7)	−0.07674 (13)	0.0471 (4)
H13	0.1524	0.4362	−0.1004	0.056*
C5	0.5387 (2)	0.51709 (7)	0.28813 (13)	0.0508 (4)
N3	0.53552 (18)	0.34709 (6)	0.18772 (12)	0.0527 (4)
H3	0.4677	0.3388	0.1389	0.063*
C22	0.1889 (2)	0.34023 (7)	0.09339 (13)	0.0467 (4)
H22	0.1425	0.3560	0.1520	0.056*
O1	0.1768 (2)	0.20499 (5)	−0.04304 (11)	0.0739 (4)
C20	0.2205 (2)	0.26068 (7)	−0.02185 (14)	0.0523 (4)
C16	0.2387 (2)	0.58410 (7)	−0.00458 (15)	0.0534 (4)
H16	0.2565	0.6215	0.0194	0.064*
C19	0.3250 (2)	0.29293 (7)	−0.08088 (14)	0.0548 (5)
H19	0.3705	0.2770	−0.1397	0.066*
C18	0.3608 (2)	0.34901 (7)	−0.05119 (13)	0.0493 (4)
H18	0.4302	0.3707	−0.0909	0.059*
C15	0.1548 (2)	0.57559 (8)	−0.09457 (16)	0.0551 (5)
H15	0.1195	0.6074	−0.1326	0.066*
C23	0.6376 (2)	0.30140 (7)	0.21616 (14)	0.0517 (4)
C1	0.6987 (3)	0.48302 (9)	0.43698 (15)	0.0646 (5)
C21	0.1515 (2)	0.28481 (7)	0.06463 (14)	0.0529 (4)
H21	0.0798	0.2635	0.1033	0.063*
C33	0.0213 (2)	0.51229 (9)	−0.23006 (15)	0.0622 (5)
H33A	0.0461	0.4759	−0.2616	0.093*
H33B	0.0449	0.5430	−0.2774	0.093*
H33C	−0.0900	0.5133	−0.2139	0.093*
C4	0.5588 (3)	0.57407 (9)	0.32314 (16)	0.0680 (6)
H4	0.5125	0.6045	0.2861	0.082*
C26	0.8354 (2)	0.20560 (8)	0.25512 (18)	0.0661 (5)
C28	0.7225 (3)	0.29651 (9)	0.30897 (17)	0.0732 (6)
H28	0.7150	0.3250	0.3596	0.088*
C24	0.6517 (3)	0.25781 (8)	0.14459 (18)	0.0736 (6)
H24	0.5944	0.2600	0.0820	0.088*
C25	0.7489 (3)	0.21103 (9)	0.1638 (2)	0.0809 (7)
H25	0.7562	0.1823	0.1137	0.097*
C27	0.8194 (3)	0.24844 (10)	0.3259 (2)	0.0813 (7)
H27	0.8757	0.2456	0.3888	0.098*
C29	0.7759 (3)	0.43458 (11)	0.49655 (17)	0.0853 (7)
H29A	0.8283	0.4496	0.5579	0.128*
H29B	0.8529	0.4159	0.4537	0.128*
H29C	0.6961	0.4072	0.5162	0.128*
C2	0.7139 (3)	0.53922 (11)	0.46798 (18)	0.0831 (7)
H2	0.7713	0.5473	0.5289	0.100*
C30	0.9433 (3)	0.15394 (10)	0.2742 (2)	0.0919 (8)
H30A	1.0215	0.1521	0.2208	0.138*
H30B	0.8806	0.1193	0.2731	0.138*
H30C	0.9961	0.1578	0.3408	0.138*
C3	0.6470 (3)	0.58475 (11)	0.41220 (19)	0.0859 (7)
H3A	0.6619	0.6225	0.4351	0.103*
C32	0.2335 (5)	0.18004 (10)	−0.13340 (19)	0.1118 (11)
H32A	0.2088	0.2046	−0.1917	0.168*
H32B	0.1839	0.1431	−0.1439	0.168*
H32C	0.3470	0.1752	−0.1271	0.168*

	U11	U22	U33	U12	U13	U23
C11	0.0348 (8)	0.0400 (8)	0.0498 (8)	−0.0001 (6)	0.0044 (7)	0.0023 (6)
N2	0.0441 (8)	0.0410 (7)	0.0595 (8)	−0.0014 (6)	0.0068 (7)	−0.0046 (6)
C9	0.0387 (8)	0.0436 (8)	0.0490 (9)	−0.0023 (7)	0.0078 (7)	−0.0036 (7)
C8	0.0372 (8)	0.0406 (8)	0.0480 (8)	−0.0009 (6)	0.0036 (7)	−0.0003 (6)
C17	0.0391 (8)	0.0385 (8)	0.0467 (8)	0.0003 (6)	−0.0060 (7)	0.0025 (6)
C6	0.0475 (10)	0.0572 (10)	0.0473 (9)	−0.0041 (8)	0.0044 (8)	−0.0061 (7)
C10	0.0363 (8)	0.0414 (8)	0.0582 (10)	−0.0002 (7)	0.0083 (7)	0.0000 (7)
C12	0.0359 (8)	0.0388 (8)	0.0488 (8)	0.0003 (6)	0.0045 (7)	0.0000 (6)
C7	0.0388 (8)	0.0462 (9)	0.0484 (9)	−0.0013 (7)	0.0007 (7)	0.0010 (7)
C14	0.0356 (8)	0.0539 (10)	0.0571 (10)	0.0041 (7)	0.0052 (7)	0.0107 (7)
N1	0.0479 (8)	0.0564 (9)	0.0483 (8)	−0.0009 (7)	−0.0005 (7)	−0.0016 (6)
C13	0.0409 (9)	0.0447 (9)	0.0557 (9)	0.0004 (7)	0.0028 (7)	0.0011 (7)
C5	0.0494 (10)	0.0535 (10)	0.0497 (9)	−0.0064 (8)	0.0061 (8)	−0.0097 (7)
N3	0.0519 (9)	0.0453 (8)	0.0603 (9)	0.0034 (6)	−0.0162 (7)	−0.0024 (6)
C22	0.0419 (9)	0.0458 (9)	0.0522 (9)	0.0014 (7)	−0.0011 (7)	0.0018 (7)
O1	0.1046 (12)	0.0424 (7)	0.0739 (9)	−0.0111 (7)	−0.0147 (8)	−0.0056 (6)
C20	0.0616 (11)	0.0377 (8)	0.0567 (10)	−0.0031 (7)	−0.0163 (8)	0.0017 (7)
C16	0.0444 (9)	0.0409 (9)	0.0751 (12)	0.0041 (7)	0.0066 (9)	0.0035 (8)
C19	0.0659 (12)	0.0489 (10)	0.0494 (9)	0.0032 (8)	−0.0044 (8)	−0.0061 (7)
C18	0.0534 (10)	0.0451 (9)	0.0496 (9)	−0.0033 (7)	0.0024 (8)	0.0002 (7)
C15	0.0403 (9)	0.0505 (10)	0.0746 (12)	0.0077 (8)	0.0063 (9)	0.0160 (8)
C23	0.0469 (10)	0.0455 (9)	0.0623 (10)	0.0013 (7)	−0.0075 (8)	0.0051 (8)
C1	0.0648 (13)	0.0780 (14)	0.0509 (10)	−0.0048 (10)	−0.0003 (9)	−0.0100 (9)
C21	0.0513 (10)	0.0452 (9)	0.0621 (10)	−0.0072 (8)	−0.0033 (8)	0.0074 (8)
C33	0.0490 (11)	0.0744 (13)	0.0630 (12)	0.0031 (9)	−0.0017 (9)	0.0145 (9)
C4	0.0821 (15)	0.0560 (11)	0.0660 (12)	−0.0063 (10)	0.0021 (11)	−0.0150 (9)
C26	0.0553 (12)	0.0505 (11)	0.0919 (15)	0.0047 (9)	−0.0111 (11)	0.0118 (10)
C28	0.0827 (15)	0.0653 (13)	0.0705 (13)	0.0191 (11)	−0.0235 (11)	−0.0045 (10)
C24	0.0892 (16)	0.0523 (11)	0.0778 (13)	0.0153 (10)	−0.0311 (12)	−0.0069 (10)
C25	0.0951 (18)	0.0512 (12)	0.0953 (16)	0.0183 (11)	−0.0236 (14)	−0.0100 (11)
C27	0.0821 (16)	0.0747 (14)	0.0857 (15)	0.0190 (12)	−0.0317 (13)	0.0073 (12)
C29	0.0919 (18)	0.1044 (19)	0.0587 (12)	0.0039 (14)	−0.0180 (12)	−0.0034 (12)
C2	0.0952 (19)	0.0912 (18)	0.0624 (13)	−0.0107 (14)	−0.0125 (12)	−0.0218 (12)
C30	0.0839 (17)	0.0659 (14)	0.125 (2)	0.0222 (12)	−0.0138 (15)	0.0159 (13)
C3	0.109 (2)	0.0742 (15)	0.0737 (14)	−0.0156 (14)	−0.0092 (14)	−0.0303 (12)
C32	0.209 (4)	0.0567 (14)	0.0696 (14)	−0.0158 (17)	−0.0010 (18)	−0.0162 (11)

C11—C12	1.416 (2)	C19—H19	0.9300
C11—C13	1.419 (2)	C18—H18	0.9300
C11—C10	1.426 (2)	C15—H15	0.9300
N2—C9	1.330 (2)	C23—C24	1.373 (3)
N2—C10	1.346 (2)	C23—C28	1.381 (3)
C9—C8	1.436 (2)	C1—C2	1.367 (3)
C9—C5	1.449 (2)	C1—C29	1.498 (3)
C8—C12	1.402 (2)	C21—H21	0.9300
C8—C7	1.479 (2)	C33—H33A	0.9600
C17—C18	1.386 (2)	C33—H33B	0.9600
C17—C22	1.392 (2)	C33—H33C	0.9600
C17—C12	1.498 (2)	C4—C3	1.372 (3)
C6—N1	1.383 (2)	C4—H4	0.9300
C6—C5	1.400 (3)	C26—C27	1.355 (3)
C6—C1	1.418 (3)	C26—C25	1.373 (3)
C10—C16	1.413 (2)	C26—C30	1.517 (3)
C7—N1	1.300 (2)	C28—C27	1.393 (3)
C7—N3	1.372 (2)	C28—H28	0.9300
C14—C13	1.367 (2)	C24—C25	1.375 (3)
C14—C15	1.416 (3)	C24—H24	0.9300
C14—C33	1.498 (3)	C25—H25	0.9300
C13—H13	0.9300	C27—H27	0.9300
C5—C4	1.403 (2)	C29—H29A	0.9600
N3—C23	1.405 (2)	C29—H29B	0.9600
N3—H3	0.8600	C29—H29C	0.9600
C22—C21	1.371 (2)	C2—C3	1.387 (4)
C22—H22	0.9300	C2—H2	0.9300
O1—C20	1.367 (2)	C30—H30A	0.9600
O1—C32	1.390 (3)	C30—H30B	0.9600
C20—C19	1.388 (3)	C30—H30C	0.9600
C20—C21	1.381 (3)	C3—H3A	0.9300
C16—C15	1.356 (3)	C32—H32A	0.9600
C16—H16	0.9300	C32—H32B	0.9600
C19—C18	1.385 (2)	C32—H32C	0.9600
C12—C11—C13	123.91 (14)	C24—C23—C28	117.96 (17)
C12—C11—C10	117.89 (15)	C24—C23—N3	116.10 (16)
C13—C11—C10	118.20 (14)	C28—C23—N3	125.94 (17)
C9—N2—C10	119.11 (14)	C2—C1—C6	117.7 (2)
N2—C9—C8	122.97 (15)	C2—C1—C29	121.8 (2)
N2—C9—C5	117.45 (15)	C6—C1—C29	120.41 (19)
C8—C9—C5	119.59 (15)	C22—C21—C20	119.92 (16)
C12—C8—C9	117.95 (15)	C22—C21—H21	120.0
C12—C8—C7	127.10 (14)	C20—C21—H21	120.0
C9—C8—C7	114.88 (14)	C14—C33—H33A	109.5
C18—C17—C22	118.13 (15)	C14—C33—H33B	109.5
C18—C17—C12	122.29 (14)	H33A—C33—H33B	109.5
C22—C17—C12	119.57 (14)	C14—C33—H33C	109.5
N1—C6—C5	122.05 (16)	H33A—C33—H33C	109.5
N1—C6—C1	117.53 (17)	H33B—C33—H33C	109.5
C5—C6—C1	120.34 (17)	C3—C4—C5	119.7 (2)
N2—C10—C16	118.44 (15)	C3—C4—H4	120.1
N2—C10—C11	122.79 (15)	C5—C4—H4	120.1
C16—C10—C11	118.76 (16)	C27—C26—C25	116.68 (19)
C8—C12—C11	119.12 (14)	C27—C26—C30	122.4 (2)
C8—C12—C17	123.54 (14)	C25—C26—C30	120.9 (2)
C11—C12—C17	117.28 (14)	C23—C28—C27	119.3 (2)
N1—C7—N3	117.69 (15)	C23—C28—H28	120.4
N1—C7—C8	124.38 (15)	C27—C28—H28	120.4
N3—C7—C8	117.88 (15)	C23—C24—C25	121.2 (2)
C13—C14—C15	118.26 (17)	C23—C24—H24	119.4
C13—C14—C33	121.96 (17)	C25—C24—H24	119.4
C15—C14—C33	119.78 (16)	C26—C25—C24	121.8 (2)
C7—N1—C6	120.05 (15)	C26—C25—H25	119.1
C14—C13—C11	122.22 (16)	C24—C25—H25	119.1
C14—C13—H13	118.9	C26—C27—C28	123.1 (2)
C11—C13—H13	118.9	C26—C27—H27	118.5
C6—C5—C4	119.60 (17)	C28—C27—H27	118.5
C6—C5—C9	118.62 (15)	C1—C29—H29A	109.5
C4—C5—C9	121.78 (18)	C1—C29—H29B	109.5
C7—N3—C23	131.31 (15)	H29A—C29—H29B	109.5
C7—N3—H3	114.3	C1—C29—H29C	109.5
C23—N3—H3	114.3	H29A—C29—H29C	109.5
C21—C22—C17	121.33 (16)	H29B—C29—H29C	109.5
C21—C22—H22	119.3	C1—C2—C3	122.6 (2)
C17—C22—H22	119.3	C1—C2—H2	118.7
C20—O1—C32	117.64 (18)	C3—C2—H2	118.7
O1—C20—C19	124.64 (17)	C26—C30—H30A	109.5
O1—C20—C21	115.29 (16)	C26—C30—H30B	109.5
C19—C20—C21	120.07 (15)	H30A—C30—H30B	109.5
C15—C16—C10	120.74 (16)	C26—C30—H30C	109.5
C15—C16—H16	119.6	H30A—C30—H30C	109.5
C10—C16—H16	119.6	H30B—C30—H30C	109.5
C20—C19—C18	119.30 (16)	C4—C3—C2	119.9 (2)
C20—C19—H19	120.3	C4—C3—H3A	120.0
C18—C19—H19	120.3	C2—C3—H3A	120.0
C17—C18—C19	121.22 (16)	O1—C32—H32A	109.5
C17—C18—H18	119.4	O1—C32—H32B	109.5
C19—C18—H18	119.4	H32A—C32—H32B	109.5
C16—C15—C14	121.74 (16)	O1—C32—H32C	109.5
C16—C15—H15	119.1	H32A—C32—H32C	109.5
C14—C15—H15	119.1	H32B—C32—H32C	109.5
C10—N2—C9—C8	−0.6 (2)	C8—C9—C5—C4	179.71 (16)
C10—N2—C9—C5	179.02 (13)	N1—C7—N3—C23	−12.1 (3)
N2—C9—C8—C12	−3.1 (2)	C8—C7—N3—C23	165.47 (16)
C5—C9—C8—C12	177.28 (13)	C18—C17—C22—C21	0.9 (2)
N2—C9—C8—C7	174.06 (14)	C12—C17—C22—C21	−178.05 (15)
C5—C9—C8—C7	−5.5 (2)	C32—O1—C20—C19	−4.0 (3)
C9—N2—C10—C16	−176.83 (14)	C32—O1—C20—C21	175.4 (2)
C9—N2—C10—C11	3.3 (2)	N2—C10—C16—C15	179.56 (15)
C12—C11—C10—N2	−2.1 (2)	C11—C10—C16—C15	−0.5 (2)
C13—C11—C10—N2	177.95 (14)	O1—C20—C19—C18	−179.70 (17)
C12—C11—C10—C16	177.95 (14)	C21—C20—C19—C18	0.9 (3)
C13—C11—C10—C16	−2.0 (2)	C22—C17—C18—C19	−1.3 (3)
C9—C8—C12—C11	4.1 (2)	C12—C17—C18—C19	177.59 (16)
C7—C8—C12—C11	−172.70 (14)	C20—C19—C18—C17	0.4 (3)
C9—C8—C12—C17	−173.20 (14)	C10—C16—C15—C14	2.5 (3)
C7—C8—C12—C17	10.0 (2)	C13—C14—C15—C16	−1.9 (2)
C13—C11—C12—C8	178.23 (14)	C33—C14—C15—C16	177.88 (16)
C10—C11—C12—C8	−1.7 (2)	C7—N3—C23—C24	−160.3 (2)
C13—C11—C12—C17	−4.3 (2)	C7—N3—C23—C28	20.4 (3)
C10—C11—C12—C17	175.80 (13)	N1—C6—C1—C2	176.14 (18)
C18—C17—C12—C8	−107.91 (19)	C5—C6—C1—C2	−0.9 (3)
C22—C17—C12—C8	71.0 (2)	N1—C6—C1—C29	−2.4 (3)
C18—C17—C12—C11	74.7 (2)	C5—C6—C1—C29	−179.42 (18)
C22—C17—C12—C11	−106.41 (17)	C17—C22—C21—C20	0.5 (3)
C12—C8—C7—N1	−175.40 (15)	O1—C20—C21—C22	179.22 (16)
C9—C8—C7—N1	7.7 (2)	C19—C20—C21—C22	−1.4 (3)
C12—C8—C7—N3	7.2 (2)	C6—C5—C4—C3	−0.3 (3)
C9—C8—C7—N3	−169.75 (14)	C9—C5—C4—C3	−179.60 (19)
N3—C7—N1—C6	173.38 (15)	C24—C23—C28—C27	0.7 (3)
C8—C7—N1—C6	−4.1 (2)	N3—C23—C28—C27	−180.0 (2)
C5—C6—N1—C7	−1.9 (2)	C28—C23—C24—C25	−0.9 (3)
C1—C6—N1—C7	−178.88 (16)	N3—C23—C24—C25	179.7 (2)
C15—C14—C13—C11	−0.7 (2)	C27—C26—C25—C24	0.5 (4)
C33—C14—C13—C11	179.49 (14)	C30—C26—C25—C24	−179.3 (2)
C12—C11—C13—C14	−177.29 (15)	C23—C24—C25—C26	0.3 (4)
C10—C11—C13—C14	2.6 (2)	C25—C26—C27—C28	−0.7 (4)
N1—C6—C5—C4	−175.65 (17)	C30—C26—C27—C28	179.1 (2)
C1—C6—C5—C4	1.2 (3)	C23—C28—C27—C26	0.1 (4)
N1—C6—C5—C9	3.7 (2)	C6—C1—C2—C3	−0.4 (4)
C1—C6—C5—C9	−179.45 (15)	C29—C1—C2—C3	178.1 (2)
N2—C9—C5—C6	−179.17 (14)	C5—C4—C3—C2	−0.9 (4)
C8—C9—C5—C6	0.4 (2)	C1—C2—C3—C4	1.3 (4)
N2—C9—C5—C4	0.1 (2)

Cg is the centroid of the C17–C22 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cg	0.86	2.48	3.336 (3)	176
C28—H28···N1	0.93	2.37	2.927 (3)	118
C18—H18···N2i	0.93	2.55	3.435 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cg	0.86	2.48	3.336 (3)	176
C28—H28⋯N1	0.93	2.37	2.927 (3)	118
C18—H18⋯N2i	0.93	2.55	3.435 (2)	159

Symmetry code: (i) .