2,2'-(Propane-1,3-di-yl)bis-(2H-indazole).

The title mol-ecule, C(17)H(16)N(4), is a bis-indazole crystallized in the rare 2H-tautomeric form. Indazole heterocycles are connected by a propane C(3) chain, and the mol-ecule is placed on a general position, in contrast to the analogous compound with a central C(2) ethane bridge, which was previously found to be placed on an inversion center in the same space group. In the title mol-ecule, indazole rings make a dihedral angle of 60.11 (7)°, and the bridging alkyl chain displays a trans conformation, resulting in a W-shaped mol-ecule. In the crystal, mol-ecules inter-act weakly through π-π contacts between inversion-related pyrazole rings, with a centroid-centroid separation of 3.746 (2) Å.

Related literature

For the synthesis of 2H-indazoles, see: Wu et al. (2010 ▶). For studies of 1H←→2H tautomerism in indazoles, see: Alkorta & Elguero (2005 ▶); Yu et al. (2006 ▶). For 2H-indazole X-ray structures, see: Saczewski et al. (2001 ▶); Rodríguez de Barbarín et al. (2006 ▶); Ramos Silva et al. (2008 ▶); Hurtado et al. (2009 ▶); Zhou et al. (2010 ▶); Long et al. (2011 ▶).

Experimental

Crystal data

C17H16N4

M = 276.34

Orthorhombic,

a = 8.182 (2) Å

b = 10.549 (4) Å

c = 34.179 (9) Å

V = 2950.1 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.60 × 0.40 × 0.18 mm

Data collection

Siemens P4 diffractometer

8195 measured reflections

2621 independent reflections

1607 reflections with I > 2σ(I)

R int = 0.042

3 standard reflections every 97 reflections intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.162

S = 1.10

2621 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029011/aa2015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029011/aa2015Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029011/aa2015Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811029011/aa2015Isup4.cml

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

C17H16N4	Dx = 1.244 Mg m−3
Mr = 276.34	Melting point: 389 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 77 reflections
a = 8.182 (2) Å	θ = 4.6–12.4°
b = 10.549 (4) Å	µ = 0.08 mm−1
c = 34.179 (9) Å	T = 298 K
V = 2950.1 (16) Å3	Prism, yellow
Z = 8	0.60 × 0.40 × 0.18 mm
F(000) = 1168

Siemens P4 diffractometer	Rint = 0.042
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2.4°
graphite	h = −9→8
ω scans	k = −12→12
8195 measured reflections	l = −40→40
2621 independent reflections	3 standard reflections every 97 reflections
1607 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0659P)2 + 0.9616P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2621 reflections	Δρmax = 0.20 e Å−3
191 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0159 (17)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
N1	0.3628 (3)	0.67210 (17)	0.33910 (5)	0.0640 (6)
N2	0.2422 (2)	0.75293 (17)	0.34924 (5)	0.0563 (5)
C1	0.2608 (3)	0.8690 (2)	0.33476 (6)	0.0622 (7)
H1A	0.1914	0.9378	0.3385	0.075*
C2	0.4896 (4)	0.9559 (3)	0.29004 (7)	0.0773 (8)
H2A	0.4529	1.0390	0.2876	0.093*
C3	0.6261 (5)	0.9172 (3)	0.27178 (8)	0.0902 (10)
H3A	0.6828	0.9744	0.2561	0.108*
C4	0.6856 (4)	0.7935 (4)	0.27562 (9)	0.0986 (11)
H4A	0.7815	0.7708	0.2628	0.118*
C5	0.6062 (4)	0.7056 (3)	0.29769 (8)	0.0847 (9)
H5A	0.6463	0.6235	0.3002	0.102*
C6	0.4614 (3)	0.7431 (2)	0.31655 (6)	0.0610 (7)
C7	0.4032 (3)	0.8675 (2)	0.31308 (6)	0.0604 (7)
C8	0.1158 (3)	0.7097 (2)	0.37586 (6)	0.0639 (7)
H8A	0.0822	0.6247	0.3686	0.077*
H8B	0.0214	0.7649	0.3737	0.077*
C9	0.1757 (3)	0.7094 (2)	0.41760 (7)	0.0646 (7)
H9A	0.2737	0.6582	0.4195	0.078*
H9B	0.2031	0.7952	0.4254	0.078*
C10	0.0474 (3)	0.6575 (3)	0.44453 (6)	0.0671 (7)
H10B	−0.0458	0.7143	0.4447	0.080*
H10C	0.0109	0.5760	0.4348	0.080*
N11	0.2399 (2)	0.56892 (18)	0.49101 (5)	0.0611 (6)
N12	0.1075 (2)	0.64232 (18)	0.48438 (5)	0.0571 (5)
C11	0.0399 (3)	0.6887 (2)	0.51674 (7)	0.0615 (7)
H11B	−0.0516	0.7409	0.5181	0.074*
C12	0.1239 (4)	0.6545 (2)	0.58912 (7)	0.0696 (7)
H12B	0.0444	0.7040	0.6012	0.083*
C13	0.2351 (3)	0.5902 (3)	0.61062 (7)	0.0699 (7)
H13B	0.2306	0.5947	0.6378	0.084*
C14	0.3567 (3)	0.5170 (2)	0.59287 (8)	0.0707 (7)
H14C	0.4308	0.4737	0.6086	0.085*
C15	0.3702 (3)	0.5070 (2)	0.55328 (7)	0.0683 (7)
H15B	0.4538	0.4603	0.5418	0.082*
C16	0.2530 (3)	0.5701 (2)	0.53037 (6)	0.0533 (6)
C17	0.1312 (3)	0.6448 (2)	0.54797 (7)	0.0555 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0772 (15)	0.0555 (11)	0.0593 (11)	0.0036 (11)	0.0102 (11)	0.0011 (9)
N2	0.0647 (13)	0.0543 (10)	0.0499 (10)	0.0009 (10)	0.0040 (10)	0.0007 (8)
C1	0.0780 (18)	0.0525 (13)	0.0560 (13)	0.0050 (12)	−0.0062 (14)	0.0031 (10)
C2	0.107 (2)	0.0695 (16)	0.0558 (14)	−0.0202 (17)	−0.0037 (16)	0.0056 (12)
C3	0.113 (3)	0.095 (2)	0.0633 (17)	−0.036 (2)	0.0138 (18)	0.0004 (15)
C4	0.100 (3)	0.118 (3)	0.0780 (19)	−0.011 (2)	0.0320 (18)	−0.0046 (19)
C5	0.095 (2)	0.0832 (19)	0.0754 (17)	0.0069 (18)	0.0252 (17)	−0.0047 (15)
C6	0.0760 (17)	0.0596 (14)	0.0474 (12)	−0.0041 (13)	0.0039 (12)	−0.0038 (10)
C7	0.0796 (18)	0.0570 (13)	0.0447 (12)	−0.0064 (13)	−0.0031 (12)	0.0003 (10)
C8	0.0633 (16)	0.0713 (15)	0.0572 (13)	−0.0018 (13)	0.0053 (12)	0.0041 (11)
C9	0.0662 (17)	0.0707 (15)	0.0570 (13)	−0.0090 (13)	0.0045 (12)	0.0051 (12)
C10	0.0665 (17)	0.0764 (16)	0.0583 (14)	−0.0086 (14)	0.0020 (13)	0.0044 (12)
N11	0.0601 (13)	0.0607 (12)	0.0626 (11)	0.0070 (10)	0.0088 (10)	0.0013 (9)
N12	0.0542 (12)	0.0595 (11)	0.0576 (11)	0.0007 (10)	0.0071 (10)	0.0047 (9)
C11	0.0608 (16)	0.0610 (14)	0.0628 (15)	0.0081 (12)	0.0103 (12)	0.0004 (11)
C12	0.0737 (18)	0.0719 (16)	0.0631 (15)	0.0076 (15)	0.0085 (14)	−0.0050 (12)
C13	0.0792 (19)	0.0731 (16)	0.0574 (13)	0.0005 (16)	−0.0023 (14)	0.0011 (12)
C14	0.0732 (19)	0.0667 (15)	0.0724 (16)	0.0059 (14)	−0.0063 (14)	0.0087 (13)
C15	0.0687 (17)	0.0639 (14)	0.0724 (16)	0.0098 (13)	0.0054 (14)	0.0012 (12)
C16	0.0535 (14)	0.0470 (11)	0.0593 (13)	−0.0014 (11)	0.0061 (11)	0.0023 (10)
C17	0.0570 (15)	0.0505 (12)	0.0590 (13)	0.0018 (11)	0.0072 (12)	0.0015 (10)

N1—C6	1.343 (3)	C9—H9A	0.9700
N1—N2	1.350 (3)	C9—H9B	0.9700
N2—C1	1.329 (3)	C10—N12	1.457 (3)
N2—C8	1.451 (3)	C10—H10B	0.9700
C1—C7	1.381 (4)	C10—H10C	0.9700
C1—H1A	0.9300	N11—C16	1.350 (3)
C2—C3	1.343 (4)	N11—N12	1.351 (3)
C2—C7	1.410 (3)	N12—C11	1.330 (3)
C2—H2A	0.9300	C11—C17	1.383 (3)
C3—C4	1.400 (5)	C11—H11B	0.9300
C3—H3A	0.9300	C12—C13	1.353 (4)
C4—C5	1.360 (4)	C12—C17	1.411 (3)
C4—H4A	0.9300	C12—H12B	0.9300
C5—C6	1.406 (4)	C13—C14	1.398 (4)
C5—H5A	0.9300	C13—H13B	0.9300
C6—C7	1.401 (3)	C14—C15	1.362 (4)
C8—C9	1.509 (3)	C14—H14C	0.9300
C8—H8A	0.9700	C15—C16	1.405 (3)
C8—H8B	0.9700	C15—H15B	0.9300
C9—C10	1.499 (3)	C16—C17	1.406 (3)
C6—N1—N2	103.55 (18)	C10—C9—H9B	109.5
C1—N2—N1	113.7 (2)	C8—C9—H9B	109.5
C1—N2—C8	127.2 (2)	H9A—C9—H9B	108.1
N1—N2—C8	118.95 (18)	N12—C10—C9	112.2 (2)
N2—C1—C7	106.6 (2)	N12—C10—H10B	109.2
N2—C1—H1A	126.7	C9—C10—H10B	109.2
C7—C1—H1A	126.7	N12—C10—H10C	109.2
C3—C2—C7	118.4 (3)	C9—C10—H10C	109.2
C3—C2—H2A	120.8	H10B—C10—H10C	107.9
C7—C2—H2A	120.8	C16—N11—N12	103.05 (18)
C2—C3—C4	121.9 (3)	C11—N12—N11	113.89 (19)
C2—C3—H3A	119.0	C11—N12—C10	126.6 (2)
C4—C3—H3A	119.0	N11—N12—C10	119.37 (19)
C5—C4—C3	121.5 (3)	N12—C11—C17	107.1 (2)
C5—C4—H4A	119.3	N12—C11—H11B	126.5
C3—C4—H4A	119.3	C17—C11—H11B	126.5
C4—C5—C6	117.7 (3)	C13—C12—C17	118.5 (2)
C4—C5—H5A	121.1	C13—C12—H12B	120.8
C6—C5—H5A	121.1	C17—C12—H12B	120.8
N1—C6—C7	111.5 (2)	C12—C13—C14	121.4 (2)
N1—C6—C5	127.7 (2)	C12—C13—H13B	119.3
C7—C6—C5	120.7 (2)	C14—C13—H13B	119.3
C1—C7—C6	104.6 (2)	C15—C14—C13	122.1 (2)
C1—C7—C2	135.6 (3)	C15—C14—H14C	118.9
C6—C7—C2	119.8 (3)	C13—C14—H14C	118.9
N2—C8—C9	111.3 (2)	C14—C15—C16	117.5 (2)
N2—C8—H8A	109.4	C14—C15—H15B	121.2
C9—C8—H8A	109.4	C16—C15—H15B	121.2
N2—C8—H8B	109.4	N11—C16—C15	127.3 (2)
C9—C8—H8B	109.4	N11—C16—C17	112.0 (2)
H8A—C8—H8B	108.0	C15—C16—C17	120.7 (2)
C10—C9—C8	110.7 (2)	C11—C17—C16	103.9 (2)
C10—C9—H9A	109.5	C11—C17—C12	136.2 (2)
C8—C9—H9A	109.5	C16—C17—C12	119.8 (2)
C6—N1—N2—C1	−0.6 (2)	C8—C9—C10—N12	173.5 (2)
C6—N1—N2—C8	−176.64 (19)	C16—N11—N12—C11	0.5 (3)
N1—N2—C1—C7	0.3 (3)	C16—N11—N12—C10	−176.1 (2)
C8—N2—C1—C7	176.0 (2)	C9—C10—N12—C11	126.4 (3)
C7—C2—C3—C4	−1.2 (4)	C9—C10—N12—N11	−57.4 (3)
C2—C3—C4—C5	1.0 (5)	N11—N12—C11—C17	0.0 (3)
C3—C4—C5—C6	0.2 (5)	C10—N12—C11—C17	176.3 (2)
N2—N1—C6—C7	0.6 (3)	C17—C12—C13—C14	1.0 (4)
N2—N1—C6—C5	−179.3 (2)	C12—C13—C14—C15	0.3 (4)
C4—C5—C6—N1	178.9 (3)	C13—C14—C15—C16	−2.1 (4)
C4—C5—C6—C7	−1.0 (4)	N12—N11—C16—C15	179.2 (2)
N2—C1—C7—C6	0.1 (2)	N12—N11—C16—C17	−0.8 (2)
N2—C1—C7—C2	178.5 (3)	C14—C15—C16—N11	−177.3 (2)
N1—C6—C7—C1	−0.5 (3)	C14—C15—C16—C17	2.7 (4)
C5—C6—C7—C1	179.5 (2)	N12—C11—C17—C16	−0.5 (3)
N1—C6—C7—C2	−179.2 (2)	N12—C11—C17—C12	−177.6 (3)
C5—C6—C7—C2	0.8 (4)	N11—C16—C17—C11	0.8 (3)
C3—C2—C7—C1	−177.9 (3)	C15—C16—C17—C11	−179.2 (2)
C3—C2—C7—C6	0.4 (4)	N11—C16—C17—C12	178.5 (2)
C1—N2—C8—C9	−97.6 (3)	C15—C16—C17—C12	−1.5 (3)
N1—N2—C8—C9	77.9 (3)	C13—C12—C17—C11	176.4 (3)
N2—C8—C9—C10	−176.7 (2)	C13—C12—C17—C16	−0.4 (4)