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The molecule of the title compound, C
16H
14N
4, 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
CCDC reference: 629456
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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(2
H-indazole)
top
Crystal data top
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) Å3 | Prism, pale yellow |
Z = 4 | 0.5 × 0.5 × 0.4 mm |
F(000) = 552 | |
Data collection top
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 top
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)] = 0.040 | All 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 reflections | Δρmax = 0.15 e Å−3 |
120 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C10i | 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—C10i | 110.09 (12) |
C4—C5—C6 | 121.55 (12) | N2—C10—H10B | 109.3 (9) |
C4—C5—H5 | 120.1 (9) | C10i—C10—H10B | 109.8 (9) |
C6—C5—H5 | 118.3 (9) | N2—C10—H10A | 108.0 (8) |
C7—C6—C5 | 122.01 (12) | C10i—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—C10i | −104.20 (16) |
C6—C7—C8—N1 | −179.93 (11) | N1—N2—C10—C10i | 70.57 (17) |
C6—C7—C8—C9 | 0.36 (16) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cgii | 0.962 (16) | 2.928 (15) | 3.7523 (15) | 144.4 (11) |
C10—H10B···Cgiii | 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. |
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