Tris[2-(2H-indazol-2-yl)eth-yl]amine.

The title tertiary amine, C(27)H(27)N(7), a potential tripodal ligand for coordination chemistry, crystallizes with the central N atom located on a threefold axis of a trigonal cell. The gauche conformation of the N(amime)-CH(2)-CH(2)-N(indazole) chain [torsion angle = -64.2 (2)°] places the pendant 2H-indazole heterocycles surrounding the symmetry axis, affording a claw-like shaped mol-ecule. Two symmetry-related indazole planes in the mol-ecule make an acute angle of 60.39 (4)°. The lone pair of the tertiary N atom is located inside the cavity, and should thus be inactive (as a ligand). In the crystal, neither significant π-π nor C-H⋯π inter-actions between molecules are found.

Related literature

For the pharmacological properties of indazoles, see: Cerecetto et al. (2005 ▶); Ryu et al. (2001 ▶); Teixeira et al. (2009 ▶). For isomerism in indazoles, see: Teixeira et al. (2006 ▶); Alkorta & Elguero (2005 ▶). For structures of related bis-(2H-indazoles), see: Rodríguez de Barbarín et al. (2006 ▶); Ovalle et al. (2011 ▶). For the structure of the precursor used in the synthesis of the title compound, see: McKee et al. (2006 ▶).

Experimental

Crystal data

C27H27N7

M = 449.56

Trigonal,

a = 13.7314 (15) Å

c = 22.235 (3) Å

V = 3630.8 (8) Å3

Z = 6

Mo Kα radiation

μ = 0.08 mm−1

T = 130 K

0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini diffractometer

Absorption correction: multi-scan [CrysAlis PRO (Oxford Diffraction, 2009 ▶); based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.509, T max = 1.000

2900 measured reflections

1404 independent reflections

852 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.131

S = 0.96

1404 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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, global. DOI: 10.1107/S1600536812022027/lr2063sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022027/lr2063Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022027/lr2063Isup3.cml

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

C27H27N7	Dx = 1.234 Mg m−3
Mr = 449.56	Melting point: 445 K
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3	Cell parameters from 1214 reflections
a = 13.7314 (15) Å	θ = 3.5–29.5°
c = 22.235 (3) Å	µ = 0.08 mm−1
V = 3630.8 (8) Å3	T = 130 K
Z = 6	Plate, orange
F(000) = 1428	0.40 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur Atlas Gemini diffractometer	1404 independent reflections
Radiation source: Enhance (Mo) X-ray Source	852 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 10.4685 pixels mm-1	θmax = 25.3°, θmin = 3.6°
ω scans	h = −16→11
Absorption correction: multi-scan [CrysAlis PRO (Oxford Diffraction, 2009); based on expressions derived by Clark & Reid (1995)]	k = −11→16
Tmin = 0.509, Tmax = 1.000	l = −18→26
2900 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0792P)2] where P = (Fo2 + 2Fc2)/3
1404 reflections	(Δ/σ)max < 0.001
103 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
N1	0.06603 (12)	0.53619 (12)	0.91972 (8)	0.0708 (5)
N2	0.14166 (12)	0.50358 (11)	0.93250 (7)	0.0667 (5)
N3	0.3333	0.6667	1.01076 (10)	0.0624 (7)
C1	0.19002 (14)	0.48969 (15)	0.88423 (10)	0.0724 (6)
H1A	0.2435	0.4671	0.8839	0.087*
C2	0.16242 (17)	0.51736 (19)	0.77209 (10)	0.0881 (7)
H2A	0.2129	0.4981	0.7558	0.106*
C3	0.1031 (2)	0.54814 (19)	0.73614 (11)	0.0956 (8)
H3A	0.1128	0.5501	0.6947	0.115*
C4	0.0267 (2)	0.57740 (17)	0.76090 (12)	0.0932 (8)
H4A	−0.0127	0.5990	0.7353	0.112*
C5	0.00892 (17)	0.57496 (15)	0.82125 (12)	0.0822 (6)
H5A	−0.0423	0.5938	0.8369	0.099*
C6	0.06970 (13)	0.54348 (13)	0.85902 (10)	0.0625 (5)
C7	0.14644 (13)	0.51492 (14)	0.83448 (9)	0.0647 (5)
C8	0.15877 (17)	0.48420 (16)	0.99499 (9)	0.0802 (6)
H8A	0.2021	0.4460	0.9963	0.096*
H8B	0.0863	0.4351	1.0133	0.096*
C9	0.21862 (15)	0.59058 (16)	1.03092 (8)	0.0771 (6)
H9A	0.1761	0.6295	1.0287	0.093*
H9B	0.2206	0.5714	1.0727	0.093*

	U11	U22	U33	U12	U13	U23
N1	0.0597 (10)	0.0648 (9)	0.0921 (13)	0.0343 (8)	0.0033 (8)	0.0052 (8)
N2	0.0544 (9)	0.0587 (9)	0.0845 (12)	0.0265 (7)	−0.0009 (8)	0.0072 (7)
N3	0.0626 (10)	0.0626 (10)	0.0621 (16)	0.0313 (5)	0.000	0.000
C1	0.0472 (10)	0.0709 (12)	0.0993 (16)	0.0298 (9)	0.0048 (10)	0.0007 (10)
C2	0.0654 (13)	0.0928 (16)	0.0912 (17)	0.0283 (11)	−0.0011 (11)	−0.0138 (12)
C3	0.0872 (16)	0.0865 (16)	0.0829 (17)	0.0209 (13)	−0.0145 (13)	−0.0056 (12)
C4	0.0903 (16)	0.0622 (13)	0.110 (2)	0.0255 (12)	−0.0399 (14)	−0.0024 (12)
C5	0.0740 (13)	0.0594 (12)	0.1138 (19)	0.0338 (10)	−0.0214 (12)	−0.0076 (11)
C6	0.0464 (10)	0.0429 (9)	0.0907 (15)	0.0168 (8)	−0.0048 (9)	0.0011 (8)
C7	0.0417 (9)	0.0580 (11)	0.0835 (14)	0.0168 (8)	−0.0031 (9)	−0.0060 (9)
C8	0.0712 (13)	0.0675 (13)	0.0906 (15)	0.0262 (10)	−0.0005 (10)	0.0155 (10)
C9	0.0736 (13)	0.0812 (14)	0.0715 (14)	0.0349 (11)	0.0126 (10)	0.0132 (10)

N1—N2	1.351 (2)	C3—C4	1.410 (3)
N1—C6	1.353 (2)	C3—H3A	0.9300
N2—C1	1.325 (2)	C4—C5	1.361 (3)
N2—C8	1.456 (2)	C4—H4A	0.9300
N3—C9i	1.4588 (19)	C5—C6	1.396 (3)
N3—C9	1.4588 (19)	C5—H5A	0.9300
N3—C9ii	1.4588 (19)	C6—C7	1.405 (2)
C1—C7	1.382 (3)	C8—C9	1.499 (3)
C1—H1A	0.9300	C8—H8A	0.9700
C2—C3	1.351 (3)	C8—H8B	0.9700
C2—C7	1.402 (3)	C9—H9A	0.9700
C2—H2A	0.9300	C9—H9B	0.9700
N2—N1—C6	103.18 (13)	C4—C5—H5A	120.9
C1—N2—N1	113.64 (15)	C6—C5—H5A	120.9
C1—N2—C8	127.49 (17)	N1—C6—C5	128.11 (18)
N1—N2—C8	118.84 (15)	N1—C6—C7	111.85 (16)
C9i—N3—C9	110.99 (10)	C5—C6—C7	120.0 (2)
C9i—N3—C9ii	110.99 (11)	C1—C7—C2	135.71 (19)
C9—N3—C9ii	110.99 (11)	C1—C7—C6	103.79 (18)
N2—C1—C7	107.54 (17)	C2—C7—C6	120.51 (18)
N2—C1—H1A	126.2	N2—C8—C9	112.99 (15)
C7—C1—H1A	126.2	N2—C8—H8A	109.0
C3—C2—C7	118.8 (2)	C9—C8—H8A	109.0
C3—C2—H2A	120.6	N2—C8—H8B	109.0
C7—C2—H2A	120.6	C9—C8—H8B	109.0
C2—C3—C4	120.6 (2)	H8A—C8—H8B	107.8
C2—C3—H3A	119.7	N3—C9—C8	113.80 (16)
C4—C3—H3A	119.7	N3—C9—H9A	108.8
C5—C4—C3	121.9 (2)	C8—C9—H9A	108.8
C5—C4—H4A	119.1	N3—C9—H9B	108.8
C3—C4—H4A	119.1	C8—C9—H9B	108.8
C4—C5—C6	118.2 (2)	H9A—C9—H9B	107.7
C6—N1—N2—C1	−0.53 (18)	N2—C1—C7—C6	−0.23 (18)
C6—N1—N2—C8	−178.56 (14)	C3—C2—C7—C1	−179.5 (2)
N1—N2—C1—C7	0.49 (19)	C3—C2—C7—C6	0.3 (3)
C8—N2—C1—C7	178.32 (15)	N1—C6—C7—C1	−0.10 (18)
C7—C2—C3—C4	0.1 (3)	C5—C6—C7—C1	179.66 (15)
C2—C3—C4—C5	−0.6 (3)	N1—C6—C7—C2	−179.97 (14)
C3—C4—C5—C6	0.7 (3)	C5—C6—C7—C2	−0.2 (2)
N2—N1—C6—C5	−179.36 (16)	C1—N2—C8—C9	111.2 (2)
N2—N1—C6—C7	0.37 (18)	N1—N2—C8—C9	−71.1 (2)
C4—C5—C6—N1	179.45 (17)	C9i—N3—C9—C8	159.04 (17)
C4—C5—C6—C7	−0.3 (2)	C9ii—N3—C9—C8	−77.0 (3)
N2—C1—C7—C2	179.62 (19)	N2—C8—C9—N3	−64.2 (2)