2,2′-(Ethane-1,2-di­yl)bis­(2H-indazole)

The molecule of the title compound, C₁₆H₁₄N₄, lies on an inversion center. The crystal structure is built up by weak C—H...π and π–π inter­actions involving the indazole ring systems.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.040
• wR factor = 0.106
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL-Plus (Siemens, 1996); program(s) used to solve structure: SHELXTL-Plus; program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL-Plus.

2,2'-(Ethane-1,2-diyl)bis(2H-indazole)

Crystal data

C16H14N4	Dx = 1.318 Mg m^−3
Mr = 262.31	Melting point: 354 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 71 reflections
a = 9.8781 (8) Å	θ = 4.6–13.0°
b = 6.9451 (5) Å	µ = 0.08 mm^−1
c = 19.2655 (15) Å	T = 296 K
V = 1321.70 (18) Å^3	Prism, pale yellow
Z = 4	0.5 × 0.5 × 0.4 mm
F(000) = 552

Data collection

Bruker P4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.1°
Graphite monochromator	h = −13→1
2θ/ω scans	k = −9→8
4200 measured reflections	l = −1→27
1918 independent reflections	3 standard reflections every 97 reflections
1345 reflections with I > 2σ(I)	intensity decay: 2.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0444P)^2 + 0.1528P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1918 reflections	Δρmax = 0.15 e Å^−3
120 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0074 (15)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.59166 (9)	0.17432 (13)	0.44690 (5)	0.0429 (3)
N2	0.47135 (9)	0.25610 (14)	0.46334 (5)	0.0412 (2)
C3	0.36684 (12)	0.19284 (17)	0.42518 (6)	0.0449 (3)
H3	0.2765 (14)	0.238 (2)	0.4339 (6)	0.056 (4)*
C4	0.36583 (14)	−0.06083 (19)	0.32593 (6)	0.0519 (3)
H4	0.2690 (14)	−0.0517 (18)	0.3148 (7)	0.057 (4)*
C5	0.45236 (16)	−0.17964 (19)	0.29152 (7)	0.0560 (3)
H5	0.4192 (14)	−0.262 (2)	0.2551 (8)	0.065 (4)*
C6	0.59192 (15)	−0.18673 (18)	0.30804 (7)	0.0531 (3)
H6	0.6496 (15)	−0.271 (2)	0.2836 (8)	0.069 (4)*
C7	0.64706 (13)	−0.07436 (17)	0.35875 (7)	0.0474 (3)
H7	0.7423 (15)	−0.0810 (19)	0.3709 (7)	0.062 (4)*
C8	0.55941 (11)	0.05113 (15)	0.39522 (6)	0.0383 (3)
C9	0.41887 (11)	0.05751 (15)	0.37927 (6)	0.0407 (3)
C10	0.46779 (14)	0.40905 (16)	0.51469 (7)	0.0468 (3)
H10B	0.5171 (14)	0.368 (2)	0.5562 (8)	0.058 (4)*
H10A	0.3743 (15)	0.4330 (18)	0.5264 (7)	0.053 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0415 (5)	0.0408 (5)	0.0463 (5)	0.0003 (4)	0.0009 (4)	−0.0034 (4)
N2	0.0445 (5)	0.0355 (4)	0.0436 (5)	−0.0006 (4)	0.0051 (4)	−0.0009 (4)
C3	0.0401 (6)	0.0447 (6)	0.0497 (6)	0.0017 (5)	0.0024 (5)	0.0043 (5)
C4	0.0520 (7)	0.0572 (8)	0.0463 (7)	−0.0114 (6)	−0.0068 (6)	0.0019 (6)
C5	0.0740 (9)	0.0511 (7)	0.0430 (6)	−0.0149 (7)	−0.0023 (6)	−0.0067 (5)
C6	0.0671 (8)	0.0431 (7)	0.0491 (7)	0.0010 (6)	0.0096 (6)	−0.0049 (5)
C7	0.0483 (7)	0.0422 (6)	0.0518 (7)	0.0030 (5)	0.0023 (5)	−0.0013 (5)
C8	0.0433 (6)	0.0332 (5)	0.0382 (5)	−0.0022 (4)	0.0007 (5)	0.0035 (4)
C9	0.0433 (6)	0.0391 (6)	0.0396 (6)	−0.0038 (5)	−0.0005 (4)	0.0054 (4)
C10	0.0584 (8)	0.0384 (6)	0.0436 (6)	−0.0023 (5)	0.0118 (6)	−0.0034 (5)

Geometric parameters (Å, º)

N1—C8	1.3509 (14)	C5—H5	0.962 (16)
N1—N2	1.3547 (13)	C6—C7	1.3639 (18)
N2—C3	1.3413 (15)	C6—H6	0.944 (16)
N2—C10	1.4520 (15)	C7—C8	1.4151 (16)
C3—C9	1.3892 (16)	C7—H7	0.971 (15)
C3—H3	0.961 (13)	C8—C9	1.4226 (16)
C4—C5	1.3605 (19)	C10—C10^i	1.524 (2)
C4—C9	1.4163 (16)	C10—H10B	0.979 (15)
C4—H4	0.982 (14)	C10—H10A	0.965 (14)
C5—C6	1.416 (2)
C8—N1—N2	103.36 (9)	C6—C7—C8	117.63 (12)
C3—N2—N1	114.18 (9)	C6—C7—H7	122.2 (8)
C3—N2—C10	126.47 (10)	C8—C7—H7	120.1 (8)
N1—N2—C10	119.16 (10)	N1—C8—C7	127.72 (11)
N2—C3—C9	106.61 (10)	N1—C8—C9	111.68 (10)
N2—C3—H3	120.8 (8)	C7—C8—C9	120.60 (10)
C9—C3—H3	132.5 (8)	C3—C9—C4	135.87 (12)
C5—C4—C9	118.24 (12)	C3—C9—C8	104.16 (10)
C5—C4—H4	123.0 (8)	C4—C9—C8	119.97 (11)
C9—C4—H4	118.8 (8)	N2—C10—C10^i	110.09 (12)
C4—C5—C6	121.55 (12)	N2—C10—H10B	109.3 (9)
C4—C5—H5	120.1 (9)	C10^i—C10—H10B	109.8 (9)
C6—C5—H5	118.3 (9)	N2—C10—H10A	108.0 (8)
C7—C6—C5	122.01 (12)	C10^i—C10—H10A	110.1 (8)
C7—C6—H6	118.1 (9)	H10B—C10—H10A	109.5 (11)
C5—C6—H6	119.9 (9)
C8—N1—N2—C3	−0.32 (12)	N2—C3—C9—C4	−179.68 (12)
C8—N1—N2—C10	−175.71 (9)	N2—C3—C9—C8	0.12 (12)
N1—N2—C3—C9	0.12 (13)	C5—C4—C9—C3	−179.74 (13)
C10—N2—C3—C9	175.12 (10)	C5—C4—C9—C8	0.49 (17)
C9—C4—C5—C6	0.10 (19)	N1—C8—C9—C3	−0.32 (12)
C4—C5—C6—C7	−0.5 (2)	C7—C8—C9—C3	179.43 (10)
C5—C6—C7—C8	0.24 (18)	N1—C8—C9—C4	179.51 (10)
N2—N1—C8—C7	−179.35 (11)	C7—C8—C9—C4	−0.73 (16)
N2—N1—C8—C9	0.39 (11)	C3—N2—C10—C10^i	−104.20 (16)
C6—C7—C8—N1	−179.93 (11)	N1—N2—C10—C10^i	70.57 (17)
C6—C7—C8—C9	0.36 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg^ii	0.962 (16)	2.928 (15)	3.7523 (15)	144.4 (11)
C10—H10B···Cg^iii	0.979 (15)	2.868 (15)	3.6421 (14)	136.6 (10)

Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y, −z+1.