N,N,N'-Tris[(1H-indol-3-yl)meth-yl]ethane-1,2-di-amine.

In the title mol-ecule, C29H29N5, the indole ring systems are essentially planar, with maximum deviations of 0.020 (2), 0.023 (2) and 0.016 (2) Å. The dihedral angles formed between the mean planes of the three indole ring systems are 38.08 (7), 89.64 (8) and 58.28 (8)°. In the crystal, mol-ecules are connected by N-H⋯N hydrogen bonds, forming inversion dimers. An intra-molecular N-H⋯N hydrogen bond is also observed.

Related literature

For applications of indole compounds and for related structures, see: Shimazaki et al.(2009 ▶); Takani et al. (2006 ▶); Munjal et al. (2010 ▶); Zhu et al. (2012 ▶).

Experimental

Crystal data

C29H29N5

M = 447.57

Monoclinic,

a = 13.769 (3) Å

b = 10.832 (2) Å

c = 16.910 (3) Å

β = 106.512 (3)°

V = 2418.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.16 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.988, T max = 0.993

12582 measured reflections

4486 independent reflections

2785 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.114

S = 0.99

4486 reflections

319 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028225/lh5652sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028225/lh5652Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028225/lh5652Isup3.cml

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

C29H29N5	F(000) = 952
Mr = 447.57	Dx = 1.229 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2164 reflections
a = 13.769 (3) Å	θ = 2.4–20.2°
b = 10.832 (2) Å	µ = 0.07 mm−1
c = 16.910 (3) Å	T = 298 K
β = 106.512 (3)°	Block, colourless
V = 2418.2 (8) Å3	0.16 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	4486 independent reflections
Radiation source: fine-focus sealed tube	2785 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→16
Tmin = 0.988, Tmax = 0.993	k = −13→8
12582 measured reflections	l = −19→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.056P)2] where P = (Fo2 + 2Fc2)/3
4486 reflections	(Δ/σ)max < 0.001
319 parameters	Δρmax = 0.12 e Å−3
4 restraints	Δρmin = −0.17 e Å−3

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
C1	0.21660 (15)	0.20856 (19)	−0.00132 (12)	0.0548 (5)
H1A	0.2423	0.2468	−0.0432	0.066*
H1B	0.1526	0.1692	−0.0287	0.066*
C2	0.29084 (15)	0.11279 (19)	0.04444 (12)	0.0560 (5)
H2A	0.3045	0.0538	0.0058	0.067*
H2B	0.3542	0.1521	0.0736	0.067*
C3	0.32167 (15)	−0.0165 (2)	0.16844 (13)	0.0572 (6)
H3A	0.3782	0.0377	0.1932	0.069*
H3B	0.3475	−0.0868	0.1451	0.069*
C4	0.27550 (14)	−0.06000 (18)	0.23321 (12)	0.0490 (5)
C5	0.17503 (15)	−0.07432 (19)	0.22497 (13)	0.0569 (6)
H5	0.1234	−0.0572	0.1773	0.068*
C6	0.25247 (14)	−0.13274 (18)	0.35366 (12)	0.0496 (5)
C7	0.32704 (14)	−0.09563 (17)	0.31615 (12)	0.0488 (5)
C8	0.42825 (16)	−0.0998 (2)	0.36324 (14)	0.0646 (6)
H8	0.4796	−0.0758	0.3408	0.078*
C9	0.45039 (17)	−0.1402 (2)	0.44351 (15)	0.0749 (7)
H9	0.5176	−0.1418	0.4755	0.090*
C10	0.37555 (17)	−0.1784 (2)	0.47800 (14)	0.0685 (6)
H10	0.3934	−0.2066	0.5322	0.082*
C11	0.27581 (16)	−0.1753 (2)	0.43353 (13)	0.0599 (6)
H11	0.2253	−0.2012	0.4565	0.072*
C12	0.09756 (14)	0.35402 (19)	0.03092 (13)	0.0559 (6)
H12A	0.0811	0.3816	−0.0259	0.067*
H12B	0.0945	0.4251	0.0651	0.067*
C13	0.02160 (14)	0.26081 (19)	0.03937 (12)	0.0507 (5)
C14	−0.04813 (15)	0.2018 (2)	−0.02227 (13)	0.0579 (6)
H14	−0.0576	0.2164	−0.0782	0.069*
C15	−0.06722 (15)	0.12209 (19)	0.09287 (13)	0.0537 (5)
C16	0.01110 (14)	0.21007 (18)	0.11443 (12)	0.0499 (5)
C17	0.06024 (15)	0.2313 (2)	0.19794 (13)	0.0589 (6)
H17	0.1134	0.2874	0.2135	0.071*
C18	0.02882 (18)	0.1681 (2)	0.25622 (14)	0.0696 (7)
H18	0.0610	0.1816	0.3118	0.084*
C19	−0.05100 (19)	0.0836 (2)	0.23338 (16)	0.0726 (7)
H19	−0.0718	0.0433	0.2743	0.087*
C20	−0.09945 (17)	0.0584 (2)	0.15233 (16)	0.0670 (6)
H20	−0.1518	0.0011	0.1376	0.080*
C21	0.27573 (16)	0.40222 (19)	0.06586 (12)	0.0564 (6)
H21A	0.2544	0.4589	0.0198	0.068*
H21B	0.3398	0.3664	0.0645	0.068*
C22	0.29158 (14)	0.47297 (19)	0.14409 (12)	0.0517 (5)
C23	0.27479 (18)	0.5946 (2)	0.15314 (15)	0.0667 (6)
H23	0.2451	0.6483	0.1102	0.080*
C24	0.34721 (16)	0.5248 (2)	0.28034 (14)	0.0588 (6)
C25	0.33709 (15)	0.42618 (19)	0.22502 (12)	0.0509 (5)
C26	0.37186 (17)	0.3112 (2)	0.25615 (14)	0.0704 (6)
H26	0.3658	0.2439	0.2210	0.084*
C27	0.4153 (2)	0.2975 (3)	0.33937 (16)	0.0852 (8)
H27	0.4383	0.2201	0.3604	0.102*
C28	0.42564 (19)	0.3970 (3)	0.39261 (15)	0.0812 (8)
H28	0.4563	0.3854	0.4487	0.097*
C29	0.39172 (18)	0.5112 (3)	0.36443 (15)	0.0750 (7)
H29	0.3981	0.5778	0.4003	0.090*
N1	0.20034 (11)	0.30344 (14)	0.05540 (9)	0.0476 (4)
N2	0.24795 (13)	0.04946 (16)	0.10288 (11)	0.0525 (5)
H2	0.2211 (15)	0.1029 (17)	0.1248 (12)	0.063*
N3	0.16084 (13)	−0.11738 (18)	0.29652 (11)	0.0610 (5)
H3	0.1064 (14)	−0.135 (2)	0.3083 (13)	0.073*
N4	−0.10242 (13)	0.11849 (18)	0.00839 (12)	0.0606 (5)
H4	−0.1491 (16)	0.066 (2)	−0.0244 (12)	0.073*
N5	0.30761 (17)	0.62689 (19)	0.23432 (14)	0.0758 (6)
H5A	0.3038 (18)	0.6959 (18)	0.2547 (15)	0.091*

	U11	U22	U33	U12	U13	U23
C1	0.0607 (13)	0.0539 (13)	0.0514 (12)	−0.0051 (11)	0.0184 (10)	−0.0059 (10)
C2	0.0567 (12)	0.0555 (13)	0.0594 (13)	−0.0005 (11)	0.0226 (11)	−0.0058 (11)
C3	0.0540 (12)	0.0495 (13)	0.0697 (14)	0.0061 (10)	0.0202 (11)	0.0013 (11)
C4	0.0474 (12)	0.0402 (11)	0.0601 (13)	0.0007 (9)	0.0166 (10)	−0.0032 (10)
C5	0.0516 (13)	0.0594 (14)	0.0579 (14)	0.0006 (11)	0.0124 (10)	−0.0064 (11)
C6	0.0455 (11)	0.0448 (12)	0.0587 (13)	−0.0032 (10)	0.0153 (10)	−0.0102 (10)
C7	0.0474 (11)	0.0388 (11)	0.0602 (13)	0.0012 (9)	0.0152 (10)	−0.0040 (10)
C8	0.0466 (12)	0.0747 (16)	0.0742 (16)	0.0027 (11)	0.0198 (11)	0.0008 (13)
C9	0.0512 (13)	0.100 (2)	0.0687 (16)	0.0086 (13)	0.0087 (11)	0.0051 (14)
C10	0.0651 (15)	0.0786 (18)	0.0621 (14)	0.0072 (13)	0.0188 (12)	0.0015 (12)
C11	0.0617 (13)	0.0584 (14)	0.0629 (15)	−0.0043 (12)	0.0230 (11)	−0.0054 (11)
C12	0.0572 (13)	0.0482 (13)	0.0577 (13)	0.0010 (11)	0.0088 (10)	−0.0006 (10)
C13	0.0462 (11)	0.0469 (12)	0.0552 (13)	0.0008 (10)	0.0086 (9)	−0.0065 (10)
C14	0.0528 (12)	0.0604 (14)	0.0586 (13)	0.0011 (11)	0.0131 (10)	−0.0038 (11)
C15	0.0482 (12)	0.0524 (13)	0.0605 (14)	0.0021 (10)	0.0156 (10)	−0.0074 (11)
C16	0.0452 (11)	0.0468 (12)	0.0570 (13)	0.0059 (10)	0.0135 (9)	−0.0068 (10)
C17	0.0527 (12)	0.0605 (14)	0.0607 (14)	0.0054 (11)	0.0116 (10)	−0.0093 (11)
C18	0.0697 (15)	0.0787 (17)	0.0596 (15)	0.0148 (14)	0.0169 (12)	−0.0015 (13)
C19	0.0759 (16)	0.0734 (17)	0.0773 (18)	0.0112 (14)	0.0361 (14)	0.0081 (14)
C20	0.0600 (14)	0.0608 (15)	0.0851 (18)	0.0016 (12)	0.0287 (13)	−0.0036 (13)
C21	0.0630 (13)	0.0547 (13)	0.0535 (13)	−0.0103 (11)	0.0196 (10)	0.0005 (10)
C22	0.0518 (12)	0.0465 (13)	0.0583 (13)	−0.0074 (10)	0.0182 (10)	−0.0045 (10)
C23	0.0782 (16)	0.0544 (15)	0.0695 (16)	0.0008 (12)	0.0243 (12)	−0.0005 (12)
C24	0.0567 (13)	0.0581 (15)	0.0648 (15)	−0.0044 (12)	0.0224 (11)	−0.0143 (12)
C25	0.0513 (12)	0.0481 (13)	0.0532 (13)	−0.0072 (10)	0.0146 (10)	−0.0078 (10)
C26	0.0890 (17)	0.0563 (15)	0.0599 (15)	0.0042 (13)	0.0114 (12)	−0.0058 (12)
C27	0.102 (2)	0.0800 (19)	0.0637 (17)	0.0137 (16)	0.0079 (14)	0.0055 (14)
C28	0.0788 (17)	0.105 (2)	0.0564 (15)	0.0071 (16)	0.0134 (13)	−0.0044 (16)
C29	0.0732 (16)	0.092 (2)	0.0612 (16)	−0.0056 (15)	0.0221 (12)	−0.0276 (14)
N1	0.0498 (10)	0.0429 (10)	0.0498 (10)	−0.0044 (8)	0.0139 (8)	−0.0041 (8)
N2	0.0521 (10)	0.0478 (11)	0.0598 (11)	0.0021 (9)	0.0193 (8)	−0.0007 (9)
N3	0.0455 (10)	0.0755 (14)	0.0633 (12)	−0.0074 (10)	0.0176 (9)	−0.0044 (10)
N4	0.0521 (10)	0.0605 (12)	0.0669 (13)	−0.0107 (9)	0.0129 (9)	−0.0135 (10)
N5	0.0988 (15)	0.0515 (13)	0.0811 (16)	0.0023 (12)	0.0318 (12)	−0.0176 (12)

C1—N1	1.466 (2)	C15—N4	1.373 (3)
C1—C2	1.507 (3)	C15—C20	1.392 (3)
C1—H1A	0.9700	C15—C16	1.407 (3)
C1—H1B	0.9700	C16—C17	1.401 (3)
C2—N2	1.459 (2)	C17—C18	1.367 (3)
C2—H2A	0.9700	C17—H17	0.9300
C2—H2B	0.9700	C18—C19	1.398 (3)
C3—N2	1.459 (3)	C18—H18	0.9300
C3—C4	1.491 (3)	C19—C20	1.370 (3)
C3—H3A	0.9700	C19—H19	0.9300
C3—H3B	0.9700	C20—H20	0.9300
C4—C5	1.359 (3)	C21—N1	1.466 (2)
C4—C7	1.433 (3)	C21—C22	1.490 (3)
C5—N3	1.362 (3)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—N3	1.364 (3)	C22—C23	1.354 (3)
C6—C11	1.376 (3)	C22—C25	1.427 (3)
C6—C7	1.410 (3)	C23—N5	1.363 (3)
C7—C8	1.396 (3)	C23—H23	0.9300
C8—C9	1.375 (3)	C24—N5	1.373 (3)
C8—H8	0.9300	C24—C29	1.387 (3)
C9—C10	1.384 (3)	C24—C25	1.400 (3)
C9—H9	0.9300	C25—C26	1.383 (3)
C10—C11	1.366 (3)	C26—C27	1.372 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—H11	0.9300	C27—C28	1.385 (3)
C12—N1	1.463 (2)	C27—H27	0.9300
C12—C13	1.490 (3)	C28—C29	1.360 (3)
C12—H12A	0.9700	C28—H28	0.9300
C12—H12B	0.9700	C29—H29	0.9300
C13—C14	1.359 (3)	N2—H2	0.829 (16)
C13—C16	1.428 (3)	N3—H3	0.849 (16)
C14—N4	1.365 (3)	N4—H4	0.92 (2)
C14—H14	0.9300	N5—H5A	0.832 (17)
N1—C1—C2	110.75 (16)	C15—C16—C13	107.10 (17)
N1—C1—H1A	109.5	C18—C17—C16	118.9 (2)
C2—C1—H1A	109.5	C18—C17—H17	120.5
N1—C1—H1B	109.5	C16—C17—H17	120.5
C2—C1—H1B	109.5	C17—C18—C19	120.9 (2)
H1A—C1—H1B	108.1	C17—C18—H18	119.5
N2—C2—C1	108.99 (16)	C19—C18—H18	119.5
N2—C2—H2A	109.9	C20—C19—C18	121.9 (2)
C1—C2—H2A	109.9	C20—C19—H19	119.1
N2—C2—H2B	109.9	C18—C19—H19	119.1
C1—C2—H2B	109.9	C19—C20—C15	117.3 (2)
H2A—C2—H2B	108.3	C19—C20—H20	121.3
N2—C3—C4	111.29 (16)	C15—C20—H20	121.3
N2—C3—H3A	109.4	N1—C21—C22	113.73 (16)
C4—C3—H3A	109.4	N1—C21—H21A	108.8
N2—C3—H3B	109.4	C22—C21—H21A	108.8
C4—C3—H3B	109.4	N1—C21—H21B	108.8
H3A—C3—H3B	108.0	C22—C21—H21B	108.8
C5—C4—C7	106.02 (18)	H21A—C21—H21B	107.7
C5—C4—C3	126.51 (19)	C23—C22—C25	106.25 (18)
C7—C4—C3	127.47 (17)	C23—C22—C21	127.9 (2)
C4—C5—N3	110.30 (19)	C25—C22—C21	125.62 (18)
C4—C5—H5	124.8	C22—C23—N5	110.2 (2)
N3—C5—H5	124.8	C22—C23—H23	124.9
N3—C6—C11	130.32 (19)	N5—C23—H23	124.9
N3—C6—C7	106.97 (18)	N5—C24—C29	130.9 (2)
C11—C6—C7	122.70 (18)	N5—C24—C25	106.7 (2)
C8—C7—C6	118.10 (19)	C29—C24—C25	122.4 (2)
C8—C7—C4	134.7 (2)	C26—C25—C24	118.3 (2)
C6—C7—C4	107.20 (17)	C26—C25—C22	134.03 (19)
C9—C8—C7	118.6 (2)	C24—C25—C22	107.65 (19)
C9—C8—H8	120.7	C27—C26—C25	119.4 (2)
C7—C8—H8	120.7	C27—C26—H26	120.3
C8—C9—C10	121.9 (2)	C25—C26—H26	120.3
C8—C9—H9	119.1	C26—C27—C28	121.1 (2)
C10—C9—H9	119.1	C26—C27—H27	119.4
C11—C10—C9	120.9 (2)	C28—C27—H27	119.4
C11—C10—H10	119.6	C29—C28—C27	121.2 (2)
C9—C10—H10	119.6	C29—C28—H28	119.4
C10—C11—C6	117.8 (2)	C27—C28—H28	119.4
C10—C11—H11	121.1	C28—C29—C24	117.6 (2)
C6—C11—H11	121.1	C28—C29—H29	121.2
N1—C12—C13	111.60 (16)	C24—C29—H29	121.2
N1—C12—H12A	109.3	C12—N1—C1	113.12 (15)
C13—C12—H12A	109.3	C12—N1—C21	110.83 (16)
N1—C12—H12B	109.3	C1—N1—C21	110.86 (15)
C13—C12—H12B	109.3	C2—N2—C3	114.63 (16)
H12A—C12—H12B	108.0	C2—N2—H2	107.1 (14)
C14—C13—C16	105.83 (18)	C3—N2—H2	107.7 (15)
C14—C13—C12	127.4 (2)	C5—N3—C6	109.50 (17)
C16—C13—C12	126.69 (17)	C5—N3—H3	130.0 (15)
C13—C14—N4	111.3 (2)	C6—N3—H3	120.5 (15)
C13—C14—H14	124.3	C14—N4—C15	107.88 (18)
N4—C14—H14	124.3	C14—N4—H4	123.2 (13)
N4—C15—C20	130.3 (2)	C15—N4—H4	128.7 (13)
N4—C15—C16	107.87 (19)	C23—N5—C24	109.17 (19)
C20—C15—C16	121.8 (2)	C23—N5—H5A	127.4 (18)
C17—C16—C15	119.16 (19)	C24—N5—H5A	123.4 (18)
C17—C16—C13	133.73 (19)
N1—C1—C2—N2	63.4 (2)	C16—C15—C20—C19	−0.8 (3)
N2—C3—C4—C5	19.5 (3)	N1—C21—C22—C23	−118.0 (2)
N2—C3—C4—C7	−160.79 (18)	N1—C21—C22—C25	68.3 (3)
C7—C4—C5—N3	−0.6 (2)	C25—C22—C23—N5	0.5 (3)
C3—C4—C5—N3	179.15 (19)	C21—C22—C23—N5	−174.18 (19)
N3—C6—C7—C8	178.42 (18)	N5—C24—C25—C26	179.86 (19)
C11—C6—C7—C8	−1.6 (3)	C29—C24—C25—C26	0.8 (3)
N3—C6—C7—C4	−1.3 (2)	N5—C24—C25—C22	0.9 (2)
C11—C6—C7—C4	178.67 (18)	C29—C24—C25—C22	−178.12 (19)
C5—C4—C7—C8	−178.5 (2)	C23—C22—C25—C26	−179.6 (2)
C3—C4—C7—C8	1.8 (4)	C21—C22—C25—C26	−4.7 (4)
C5—C4—C7—C6	1.2 (2)	C23—C22—C25—C24	−0.9 (2)
C3—C4—C7—C6	−178.60 (19)	C21—C22—C25—C24	173.95 (18)
C6—C7—C8—C9	0.3 (3)	C24—C25—C26—C27	−0.4 (3)
C4—C7—C8—C9	179.8 (2)	C22—C25—C26—C27	178.2 (2)
C7—C8—C9—C10	1.1 (4)	C25—C26—C27—C28	−0.5 (4)
C8—C9—C10—C11	−1.2 (4)	C26—C27—C28—C29	1.0 (4)
C9—C10—C11—C6	−0.2 (4)	C27—C28—C29—C24	−0.5 (4)
N3—C6—C11—C10	−178.5 (2)	N5—C24—C29—C28	−179.1 (2)
C7—C6—C11—C10	1.6 (3)	C25—C24—C29—C28	−0.3 (3)
N1—C12—C13—C14	−108.4 (2)	C13—C12—N1—C1	68.4 (2)
N1—C12—C13—C16	67.8 (2)	C13—C12—N1—C21	−166.40 (16)
C16—C13—C14—N4	0.6 (2)	C2—C1—N1—C12	−147.38 (16)
C12—C13—C14—N4	177.40 (18)	C2—C1—N1—C21	87.41 (19)
N4—C15—C16—C17	−179.86 (17)	C22—C21—N1—C12	76.6 (2)
C20—C15—C16—C17	2.1 (3)	C22—C21—N1—C1	−156.94 (17)
N4—C15—C16—C13	0.5 (2)	C1—C2—N2—C3	−161.54 (17)
C20—C15—C16—C13	−177.50 (18)	C4—C3—N2—C2	170.19 (16)
C14—C13—C16—C17	179.8 (2)	C4—C5—N3—C6	−0.2 (2)
C12—C13—C16—C17	2.9 (3)	C11—C6—N3—C5	−179.0 (2)
C14—C13—C16—C15	−0.6 (2)	C7—C6—N3—C5	0.9 (2)
C12—C13—C16—C15	−177.50 (18)	C13—C14—N4—C15	−0.3 (2)
C15—C16—C17—C18	−1.7 (3)	C20—C15—N4—C14	177.6 (2)
C13—C16—C17—C18	177.8 (2)	C16—C15—N4—C14	−0.2 (2)
C16—C17—C18—C19	0.0 (3)	C22—C23—N5—C24	0.1 (3)
C17—C18—C19—C20	1.4 (3)	C29—C24—N5—C23	178.3 (2)
C18—C19—C20—C15	−1.0 (3)	C25—C24—N5—C23	−0.6 (3)
N4—C15—C20—C19	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2i	0.92 (2)	2.03 (2)	2.953 (3)	176 (2)
N2—H2···N1	0.83 (2)	2.45 (2)	2.889 (2)	114 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N2i	0.92 (2)	2.03 (2)	2.953 (3)	176 (2)
N2—H2⋯N1	0.83 (2)	2.45 (2)	2.889 (2)	114 (2)

Symmetry code: (i) .