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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045120/bx2032sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045120/bx2032Isup2.hkl
Contains datablock I

CCDC reference: 629456

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

No syntax errors found


No errors found in this datablock

Computing details top

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) top
Crystal data top
C16H14N4Dx = 1.318 Mg m3
Mr = 262.31Melting point: 354 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 71 reflections
a = 9.8781 (8) Åθ = 4.6–13.0°
b = 6.9451 (5) ŵ = 0.08 mm1
c = 19.2655 (15) ÅT = 296 K
V = 1321.70 (18) Å3Prism, pale yellow
Z = 40.5 × 0.5 × 0.4 mm
F(000) = 552
Data collection top
Bruker P4
diffractometer
Rint = 0.024
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 2.1°
Graphite monochromatorh = 131
2θ/ω scansk = 98
4200 measured reflectionsl = 127
1918 independent reflections3 standard reflections every 97 reflections
1345 reflections with I > 2σ(I) intensity decay: 2.9%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0444P)2 + 0.1528P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1918 reflectionsΔρmax = 0.15 e Å3
120 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0074 (15)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.59166 (9)0.17432 (13)0.44690 (5)0.0429 (3)
N20.47135 (9)0.25610 (14)0.46334 (5)0.0412 (2)
C30.36684 (12)0.19284 (17)0.42518 (6)0.0449 (3)
H30.2765 (14)0.238 (2)0.4339 (6)0.056 (4)*
C40.36583 (14)0.06083 (19)0.32593 (6)0.0519 (3)
H40.2690 (14)0.0517 (18)0.3148 (7)0.057 (4)*
C50.45236 (16)0.17964 (19)0.29152 (7)0.0560 (3)
H50.4192 (14)0.262 (2)0.2551 (8)0.065 (4)*
C60.59192 (15)0.18673 (18)0.30804 (7)0.0531 (3)
H60.6496 (15)0.271 (2)0.2836 (8)0.069 (4)*
C70.64706 (13)0.07436 (17)0.35875 (7)0.0474 (3)
H70.7423 (15)0.0810 (19)0.3709 (7)0.062 (4)*
C80.55941 (11)0.05113 (15)0.39522 (6)0.0383 (3)
C90.41887 (11)0.05751 (15)0.37927 (6)0.0407 (3)
C100.46779 (14)0.40905 (16)0.51469 (7)0.0468 (3)
H10B0.5171 (14)0.368 (2)0.5562 (8)0.058 (4)*
H10A0.3743 (15)0.4330 (18)0.5264 (7)0.053 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0415 (5)0.0408 (5)0.0463 (5)0.0003 (4)0.0009 (4)0.0034 (4)
N20.0445 (5)0.0355 (4)0.0436 (5)0.0006 (4)0.0051 (4)0.0009 (4)
C30.0401 (6)0.0447 (6)0.0497 (6)0.0017 (5)0.0024 (5)0.0043 (5)
C40.0520 (7)0.0572 (8)0.0463 (7)0.0114 (6)0.0068 (6)0.0019 (6)
C50.0740 (9)0.0511 (7)0.0430 (6)0.0149 (7)0.0023 (6)0.0067 (5)
C60.0671 (8)0.0431 (7)0.0491 (7)0.0010 (6)0.0096 (6)0.0049 (5)
C70.0483 (7)0.0422 (6)0.0518 (7)0.0030 (5)0.0023 (5)0.0013 (5)
C80.0433 (6)0.0332 (5)0.0382 (5)0.0022 (4)0.0007 (5)0.0035 (4)
C90.0433 (6)0.0391 (6)0.0396 (6)0.0038 (5)0.0005 (4)0.0054 (4)
C100.0584 (8)0.0384 (6)0.0436 (6)0.0023 (5)0.0118 (6)0.0034 (5)
Geometric parameters (Å, º) top
N1—C81.3509 (14)C5—H50.962 (16)
N1—N21.3547 (13)C6—C71.3639 (18)
N2—C31.3413 (15)C6—H60.944 (16)
N2—C101.4520 (15)C7—C81.4151 (16)
C3—C91.3892 (16)C7—H70.971 (15)
C3—H30.961 (13)C8—C91.4226 (16)
C4—C51.3605 (19)C10—C10i1.524 (2)
C4—C91.4163 (16)C10—H10B0.979 (15)
C4—H40.982 (14)C10—H10A0.965 (14)
C5—C61.416 (2)
C8—N1—N2103.36 (9)C6—C7—C8117.63 (12)
C3—N2—N1114.18 (9)C6—C7—H7122.2 (8)
C3—N2—C10126.47 (10)C8—C7—H7120.1 (8)
N1—N2—C10119.16 (10)N1—C8—C7127.72 (11)
N2—C3—C9106.61 (10)N1—C8—C9111.68 (10)
N2—C3—H3120.8 (8)C7—C8—C9120.60 (10)
C9—C3—H3132.5 (8)C3—C9—C4135.87 (12)
C5—C4—C9118.24 (12)C3—C9—C8104.16 (10)
C5—C4—H4123.0 (8)C4—C9—C8119.97 (11)
C9—C4—H4118.8 (8)N2—C10—C10i110.09 (12)
C4—C5—C6121.55 (12)N2—C10—H10B109.3 (9)
C4—C5—H5120.1 (9)C10i—C10—H10B109.8 (9)
C6—C5—H5118.3 (9)N2—C10—H10A108.0 (8)
C7—C6—C5122.01 (12)C10i—C10—H10A110.1 (8)
C7—C6—H6118.1 (9)H10B—C10—H10A109.5 (11)
C5—C6—H6119.9 (9)
C8—N1—N2—C30.32 (12)N2—C3—C9—C4179.68 (12)
C8—N1—N2—C10175.71 (9)N2—C3—C9—C80.12 (12)
N1—N2—C3—C90.12 (13)C5—C4—C9—C3179.74 (13)
C10—N2—C3—C9175.12 (10)C5—C4—C9—C80.49 (17)
C9—C4—C5—C60.10 (19)N1—C8—C9—C30.32 (12)
C4—C5—C6—C70.5 (2)C7—C8—C9—C3179.43 (10)
C5—C6—C7—C80.24 (18)N1—C8—C9—C4179.51 (10)
N2—N1—C8—C7179.35 (11)C7—C8—C9—C40.73 (16)
N2—N1—C8—C90.39 (11)C3—N2—C10—C10i104.20 (16)
C6—C7—C8—N1179.93 (11)N1—N2—C10—C10i70.57 (17)
C6—C7—C8—C90.36 (16)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···Cgii0.962 (16)2.928 (15)3.7523 (15)144.4 (11)
C10—H10B···Cgiii0.979 (15)2.868 (15)3.6421 (14)136.6 (10)
Symmetry codes: (ii) x+1, y1/2, z+1/2; (iii) x+1, y, z+1.
 

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