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In the title compound, alternatively named 5,5′-diphenyl-2,2′-methyleneditetrazole, C
15H
12N
8, the dihedral angles between the tetrazole and benzene rings in the two 5-phenyltetrazole fragments are 2.45 (6) and 10.01 (9)°. There is weak intermolecular C—H
N hydrogen bonding involving the H atoms of the methylene groups, which is responsible for the formation of two-membered aggregates. C—H
π interactions in the crystal structure are discussed.
Supporting information
CCDC reference: 192967
To prepare the title compound, a solution of 5-phenyltetrazole (0.06 mol),
diiodomethane (0.03 mol) and triethylamine (0.06 mol) in dimethylformamide (50 ml) was agitated at 373 K for 20 h. The solution was cooled to room
temperature and flushed with water (1 l). The oil which formed was left to
crystallize for several hours. The precipitate was filtered, washed with water
and vacuum dried. Crystals of (I) suitable for single-crystal X-ray analysis
were grown by slow evaporation from an ethyl acetate solution (yield 59%; m.p.
463–465 K, decomposition, uncorrected). Spectroscopic analysis: 1H NMR (100 MHz, d6-DMSO, δ, p.p.m.): 7.50–7.68 (m, 6H, C6H5), 7.88 (s, 2H,
CH2), 8.0–8.21 (m, 4H, C6H5).
H-atom positions were found from the difference Fourier map and all associated
parameters were refined freely [C—H = 0.95 (2)–1.01 (2) Å].
Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
Bis(5-phenyltetrazol-2-yl)methane
top
Crystal data top
C15H12N8 | F(000) = 632 |
Mr = 304.33 | Dx = 1.397 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
a = 11.053 (2) Å | Cell parameters from 25 reflections |
b = 7.409 (2) Å | θ = 17.5–21.8° |
c = 17.956 (4) Å | µ = 0.09 mm−1 |
β = 100.16 (2)° | T = 293 K |
V = 1447.4 (6) Å3 | Prism, colourless |
Z = 4 | 0.50 × 0.45 × 0.40 mm |
Data collection top
Nicolet R3m four-circle diffractometer | Rint = 0.015 |
Radiation source: fine-focus sealed tube | θmax = 30.1°, θmin = 2.3° |
Graphite monochromator | h = 0→15 |
ω/2θ scans | k = 0→10 |
4606 measured reflections | l = −25→24 |
4258 independent reflections | 3 standard reflections every 100 reflections |
3025 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.126 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0693P)2 + 0.0755P] where P = (Fo2 + 2Fc2)/3 |
4258 reflections | (Δ/σ)max < 0.001 |
256 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C15H12N8 | V = 1447.4 (6) Å3 |
Mr = 304.33 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.053 (2) Å | µ = 0.09 mm−1 |
b = 7.409 (2) Å | T = 293 K |
c = 17.956 (4) Å | 0.50 × 0.45 × 0.40 mm |
β = 100.16 (2)° | |
Data collection top
Nicolet R3m four-circle diffractometer | Rint = 0.015 |
4606 measured reflections | 3 standard reflections every 100 reflections |
4258 independent reflections | intensity decay: none |
3025 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.126 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.19 e Å−3 |
4258 reflections | Δρmin = −0.21 e Å−3 |
256 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.12733 (11) | 0.45902 (17) | −0.09593 (8) | 0.0477 (3) | |
H1A | 0.1173 (12) | 0.518 (2) | −0.1466 (8) | 0.053 (4)* | |
H1B | 0.1127 (13) | 0.542 (2) | −0.0542 (9) | 0.057 (4)* | |
N1A | 0.31064 (9) | 0.35311 (14) | −0.01017 (5) | 0.0437 (2) | |
N2A | 0.25352 (9) | 0.39768 (14) | −0.07944 (5) | 0.0435 (2) | |
N3A | 0.32068 (10) | 0.37400 (16) | −0.13275 (6) | 0.0519 (3) | |
N4A | 0.42708 (10) | 0.31252 (16) | −0.09787 (6) | 0.0516 (3) | |
C5A | 0.41962 (10) | 0.30024 (15) | −0.02336 (6) | 0.0402 (2) | |
C6A | 0.52024 (10) | 0.23768 (15) | 0.03519 (7) | 0.0415 (2) | |
C7A | 0.50769 (12) | 0.2363 (2) | 0.11072 (7) | 0.0512 (3) | |
H7A | 0.4346 (15) | 0.278 (2) | 0.1254 (9) | 0.062 (4)* | |
C8A | 0.60299 (14) | 0.1781 (2) | 0.16584 (8) | 0.0595 (3) | |
H8A | 0.5926 (15) | 0.185 (2) | 0.2179 (10) | 0.065 (4)* | |
C9A | 0.71158 (13) | 0.1187 (2) | 0.14608 (9) | 0.0584 (3) | |
H9A | 0.7806 (16) | 0.070 (2) | 0.1858 (10) | 0.076 (5)* | |
C10A | 0.72538 (12) | 0.1201 (2) | 0.07121 (9) | 0.0565 (3) | |
H10A | 0.8000 (15) | 0.081 (2) | 0.0555 (9) | 0.071 (5)* | |
C11A | 0.63074 (12) | 0.17982 (17) | 0.01598 (8) | 0.0491 (3) | |
H11A | 0.6419 (15) | 0.184 (2) | −0.0358 (10) | 0.067 (5)* | |
N1B | 0.03684 (9) | 0.17582 (13) | −0.14913 (5) | 0.0428 (2) | |
N2B | 0.04398 (9) | 0.30665 (13) | −0.09793 (5) | 0.0427 (2) | |
N3B | −0.02780 (11) | 0.28286 (16) | −0.04728 (6) | 0.0531 (3) | |
N4B | −0.08581 (11) | 0.13010 (16) | −0.06540 (6) | 0.0531 (3) | |
C5B | −0.04471 (9) | 0.06613 (16) | −0.12719 (6) | 0.0397 (2) | |
C6B | −0.08221 (9) | −0.10783 (16) | −0.16309 (6) | 0.0397 (2) | |
C7B | −0.04800 (11) | −0.15581 (18) | −0.23142 (7) | 0.0458 (3) | |
H7B | −0.0021 (13) | −0.075 (2) | −0.2564 (9) | 0.059 (4)* | |
C8B | −0.08235 (12) | −0.32230 (19) | −0.26353 (7) | 0.0528 (3) | |
H8B | −0.0555 (15) | −0.356 (2) | −0.3121 (9) | 0.066 (4)* | |
C9B | −0.15069 (12) | −0.4402 (2) | −0.22802 (8) | 0.0538 (3) | |
H9B | −0.1710 (15) | −0.556 (2) | −0.2488 (10) | 0.075 (5)* | |
C10B | −0.18588 (12) | −0.39208 (19) | −0.16055 (8) | 0.0522 (3) | |
H10B | −0.2349 (15) | −0.471 (2) | −0.1343 (9) | 0.070 (5)* | |
C11B | −0.15178 (11) | −0.22668 (18) | −0.12797 (7) | 0.0458 (3) | |
H11B | −0.1763 (12) | −0.1904 (19) | −0.0810 (8) | 0.050 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0459 (6) | 0.0418 (6) | 0.0534 (7) | 0.0008 (5) | 0.0027 (5) | −0.0002 (5) |
N1A | 0.0429 (5) | 0.0460 (5) | 0.0419 (5) | −0.0017 (4) | 0.0068 (4) | 0.0000 (4) |
N2A | 0.0446 (5) | 0.0434 (5) | 0.0418 (5) | −0.0029 (4) | 0.0058 (4) | −0.0002 (4) |
N3A | 0.0537 (6) | 0.0587 (6) | 0.0439 (5) | −0.0031 (5) | 0.0105 (4) | 0.0011 (5) |
N4A | 0.0494 (6) | 0.0613 (7) | 0.0459 (5) | −0.0016 (5) | 0.0129 (4) | −0.0004 (5) |
C5A | 0.0422 (6) | 0.0364 (5) | 0.0434 (5) | −0.0054 (4) | 0.0112 (4) | −0.0016 (4) |
C6A | 0.0400 (5) | 0.0362 (5) | 0.0485 (6) | −0.0039 (4) | 0.0086 (4) | −0.0005 (4) |
C7A | 0.0456 (6) | 0.0580 (7) | 0.0516 (7) | 0.0026 (6) | 0.0127 (5) | 0.0030 (6) |
C8A | 0.0613 (8) | 0.0669 (9) | 0.0499 (7) | 0.0007 (7) | 0.0091 (6) | 0.0081 (6) |
C9A | 0.0500 (7) | 0.0572 (8) | 0.0648 (8) | 0.0010 (6) | 0.0008 (6) | 0.0099 (6) |
C10A | 0.0432 (6) | 0.0555 (8) | 0.0712 (9) | 0.0033 (6) | 0.0112 (6) | 0.0026 (6) |
C11A | 0.0464 (6) | 0.0486 (7) | 0.0540 (7) | −0.0013 (5) | 0.0132 (5) | −0.0019 (5) |
N1B | 0.0413 (5) | 0.0447 (5) | 0.0428 (5) | −0.0008 (4) | 0.0087 (4) | −0.0023 (4) |
N2B | 0.0407 (5) | 0.0432 (5) | 0.0434 (5) | 0.0027 (4) | 0.0054 (4) | −0.0023 (4) |
N3B | 0.0567 (6) | 0.0559 (6) | 0.0488 (6) | 0.0000 (5) | 0.0147 (5) | −0.0071 (5) |
N4B | 0.0570 (6) | 0.0570 (6) | 0.0489 (6) | −0.0049 (5) | 0.0197 (5) | −0.0072 (5) |
C5B | 0.0346 (5) | 0.0463 (6) | 0.0379 (5) | 0.0032 (4) | 0.0054 (4) | 0.0027 (4) |
C6B | 0.0326 (5) | 0.0460 (6) | 0.0395 (5) | 0.0008 (4) | 0.0030 (4) | 0.0018 (4) |
C7B | 0.0414 (6) | 0.0535 (7) | 0.0428 (6) | −0.0014 (5) | 0.0085 (5) | 0.0007 (5) |
C8B | 0.0504 (7) | 0.0606 (8) | 0.0466 (6) | 0.0002 (6) | 0.0065 (5) | −0.0091 (6) |
C9B | 0.0460 (6) | 0.0518 (7) | 0.0592 (8) | −0.0037 (5) | −0.0028 (5) | −0.0075 (6) |
C10B | 0.0425 (6) | 0.0528 (7) | 0.0592 (7) | −0.0071 (5) | 0.0033 (5) | 0.0065 (6) |
C11B | 0.0408 (5) | 0.0543 (7) | 0.0423 (6) | −0.0017 (5) | 0.0077 (4) | 0.0040 (5) |
Geometric parameters (Å, º) top
C1—N2A | 1.4470 (16) | C10A—H10A | 0.961 (16) |
C1—N2B | 1.4535 (16) | C11A—H11A | 0.959 (17) |
C1—H1A | 0.997 (15) | N1B—C5B | 1.3242 (15) |
C1—H1B | 1.003 (15) | N1B—N2B | 1.3287 (13) |
N1A—C5A | 1.3271 (15) | N2B—N3B | 1.3200 (15) |
N1A—N2A | 1.3333 (14) | N3B—N4B | 1.3131 (16) |
N2A—N3A | 1.3223 (14) | N4B—C5B | 1.3564 (15) |
N3A—N4A | 1.3127 (16) | C5B—C6B | 1.4677 (16) |
N4A—C5A | 1.3579 (15) | C6B—C11B | 1.3913 (16) |
C5A—C6A | 1.4645 (17) | C6B—C7B | 1.3922 (16) |
C6A—C7A | 1.3873 (17) | C7B—C8B | 1.3860 (19) |
C6A—C11A | 1.3939 (17) | C7B—H7B | 0.949 (15) |
C7A—C8A | 1.3812 (19) | C8B—C9B | 1.382 (2) |
C7A—H7A | 0.945 (16) | C8B—H8B | 1.001 (16) |
C8A—C9A | 1.382 (2) | C9B—C10B | 1.383 (2) |
C8A—H8A | 0.964 (16) | C9B—H9B | 0.946 (18) |
C9A—C10A | 1.379 (2) | C10B—C11B | 1.3813 (19) |
C9A—H9A | 1.014 (19) | C10B—H10B | 0.973 (17) |
C10A—C11A | 1.3812 (19) | C11B—H11B | 0.968 (14) |
| | | |
N2A—C1—N2B | 110.18 (10) | C10A—C11A—C6A | 120.43 (13) |
N2A—C1—H1A | 105.8 (8) | C10A—C11A—H11A | 119.6 (10) |
N2B—C1—H1A | 110.4 (8) | C6A—C11A—H11A | 119.9 (10) |
N2A—C1—H1B | 108.4 (9) | C5B—N1B—N2B | 101.67 (9) |
N2B—C1—H1B | 108.0 (8) | N3B—N2B—N1B | 114.19 (10) |
H1A—C1—H1B | 114.0 (12) | N3B—N2B—C1 | 122.82 (10) |
C5A—N1A—N2A | 101.65 (10) | N1B—N2B—C1 | 122.94 (10) |
N3A—N2A—N1A | 114.11 (10) | N4B—N3B—N2B | 105.72 (10) |
N3A—N2A—C1 | 122.51 (10) | N3B—N4B—C5B | 106.53 (10) |
N1A—N2A—C1 | 123.32 (10) | N1B—C5B—N4B | 111.88 (11) |
N4A—N3A—N2A | 105.71 (10) | N1B—C5B—C6B | 124.23 (10) |
N3A—N4A—C5A | 106.75 (10) | N4B—C5B—C6B | 123.83 (10) |
N1A—C5A—N4A | 111.77 (10) | C11B—C6B—C7B | 119.71 (11) |
N1A—C5A—C6A | 124.30 (10) | C11B—C6B—C5B | 119.51 (10) |
N4A—C5A—C6A | 123.92 (10) | C7B—C6B—C5B | 120.78 (10) |
C7A—C6A—C11A | 118.86 (12) | C8B—C7B—C6B | 119.79 (12) |
C7A—C6A—C5A | 120.66 (11) | C8B—C7B—H7B | 119.8 (9) |
C11A—C6A—C5A | 120.48 (11) | C6B—C7B—H7B | 120.4 (9) |
C8A—C7A—C6A | 120.51 (12) | C9B—C8B—C7B | 120.16 (12) |
C8A—C7A—H7A | 119.0 (10) | C9B—C8B—H8B | 121.1 (10) |
C6A—C7A—H7A | 120.5 (10) | C7B—C8B—H8B | 118.7 (10) |
C7A—C8A—C9A | 120.16 (14) | C8B—C9B—C10B | 120.16 (13) |
C7A—C8A—H8A | 118.2 (10) | C8B—C9B—H9B | 120.1 (10) |
C9A—C8A—H8A | 121.6 (10) | C10B—C9B—H9B | 119.7 (10) |
C10A—C9A—C8A | 119.88 (13) | C11B—C10B—C9B | 120.12 (12) |
C10A—C9A—H9A | 119.3 (9) | C11B—C10B—H10B | 117.4 (10) |
C8A—C9A—H9A | 120.8 (9) | C9B—C10B—H10B | 122.5 (10) |
C9A—C10A—C11A | 120.14 (13) | C10B—C11B—C6B | 120.06 (12) |
C9A—C10A—H10A | 122.1 (10) | C10B—C11B—H11B | 121.2 (8) |
C11A—C10A—H10A | 117.7 (10) | C6B—C11B—H11B | 118.7 (8) |
| | | |
C5A—N1A—N2A—N3A | 0.36 (13) | C5B—N1B—N2B—N3B | −0.21 (13) |
C5A—N1A—N2A—C1 | 177.73 (10) | C5B—N1B—N2B—C1 | 177.35 (10) |
N2B—C1—N2A—N3A | 99.30 (13) | N2A—C1—N2B—N3B | 112.74 (13) |
N2B—C1—N2A—N1A | −77.85 (14) | N2A—C1—N2B—N1B | −64.61 (14) |
N1A—N2A—N3A—N4A | −0.46 (14) | N1B—N2B—N3B—N4B | −0.23 (14) |
C1—N2A—N3A—N4A | −177.85 (11) | C1—N2B—N3B—N4B | −177.79 (11) |
N2A—N3A—N4A—C5A | 0.35 (14) | N2B—N3B—N4B—C5B | 0.56 (14) |
N2A—N1A—C5A—N4A | −0.12 (13) | N2B—N1B—C5B—N4B | 0.58 (13) |
N2A—N1A—C5A—C6A | 179.37 (10) | N2B—N1B—C5B—C6B | −176.81 (10) |
N3A—N4A—C5A—N1A | −0.15 (14) | N3B—N4B—C5B—N1B | −0.75 (14) |
N3A—N4A—C5A—C6A | −179.64 (11) | N3B—N4B—C5B—C6B | 176.65 (10) |
N1A—C5A—C6A—C7A | −2.31 (18) | N1B—C5B—C6B—C11B | 168.85 (11) |
N4A—C5A—C6A—C7A | 177.13 (12) | N4B—C5B—C6B—C11B | −8.23 (17) |
N1A—C5A—C6A—C11A | 178.22 (11) | N1B—C5B—C6B—C7B | −10.54 (17) |
N4A—C5A—C6A—C11A | −2.35 (17) | N4B—C5B—C6B—C7B | 172.38 (11) |
C11A—C6A—C7A—C8A | −0.2 (2) | C11B—C6B—C7B—C8B | −0.69 (17) |
C5A—C6A—C7A—C8A | −179.67 (12) | C5B—C6B—C7B—C8B | 178.70 (11) |
C6A—C7A—C8A—C9A | −0.7 (2) | C6B—C7B—C8B—C9B | 0.21 (19) |
C7A—C8A—C9A—C10A | 0.9 (2) | C7B—C8B—C9B—C10B | 0.5 (2) |
C8A—C9A—C10A—C11A | −0.3 (2) | C8B—C9B—C10B—C11B | −0.7 (2) |
C9A—C10A—C11A—C6A | −0.6 (2) | C9B—C10B—C11B—C6B | 0.18 (19) |
C7A—C6A—C11A—C10A | 0.80 (19) | C7B—C6B—C11B—C10B | 0.49 (17) |
C5A—C6A—C11A—C10A | −179.71 (12) | C5B—C6B—C11B—C10B | −178.90 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···N3Bi | 1.003 (15) | 2.548 (15) | 3.5324 (18) | 166.9 (12) |
C10A—H10A···CgTzii | 0.961 (16) | 3.116 (16) | 3.9153 (18) | 141.6 (12) |
C9B—H9B···CgBziii | 0.946 (18) | 2.877 (16) | 3.6548 (18) | 140.1 (13) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z; (iii) −x−1/2, y−1/2, −z−1/2. |
Experimental details
Crystal data |
Chemical formula | C15H12N8 |
Mr | 304.33 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.053 (2), 7.409 (2), 17.956 (4) |
β (°) | 100.16 (2) |
V (Å3) | 1447.4 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.45 × 0.40 |
|
Data collection |
Diffractometer | Nicolet R3m four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4606, 4258, 3025 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.705 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.126, 1.04 |
No. of reflections | 4258 |
No. of parameters | 256 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.19, −0.21 |
Selected geometric parameters (Å, º) topC1—N2A | 1.4470 (16) | C5A—C6A | 1.4645 (17) |
C1—N2B | 1.4535 (16) | N1B—C5B | 1.3242 (15) |
N1A—C5A | 1.3271 (15) | N1B—N2B | 1.3287 (13) |
N1A—N2A | 1.3333 (14) | N2B—N3B | 1.3200 (15) |
N2A—N3A | 1.3223 (14) | N3B—N4B | 1.3131 (16) |
N3A—N4A | 1.3127 (16) | N4B—C5B | 1.3564 (15) |
N4A—C5A | 1.3579 (15) | C5B—C6B | 1.4677 (16) |
| | | |
N2A—C1—N2B | 110.18 (10) | C5B—N1B—N2B | 101.67 (9) |
C5A—N1A—N2A | 101.65 (10) | N3B—N2B—N1B | 114.19 (10) |
N3A—N2A—N1A | 114.11 (10) | N4B—N3B—N2B | 105.72 (10) |
N4A—N3A—N2A | 105.71 (10) | N3B—N4B—C5B | 106.53 (10) |
N3A—N4A—C5A | 106.75 (10) | N1B—C5B—N4B | 111.88 (11) |
N1A—C5A—N4A | 111.77 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···N3Bi | 1.003 (15) | 2.548 (15) | 3.5324 (18) | 166.9 (12) |
C10A—H10A···CgTzii | 0.961 (16) | 3.116 (16) | 3.9153 (18) | 141.6 (12) |
C9B—H9B···CgBziii | 0.946 (18) | 2.877 (16) | 3.6548 (18) | 140.1 (13) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z; (iii) −x−1/2, y−1/2, −z−1/2. |
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In recent years, binuclear tetrazoles have been of great interest, owing to their potential effectiveness as chelating agents and also due to their potential for use as starting materials for the synthesis of some organometallic structures with important physical properties (Saalfrank et al., 1995, 1996; Lyakhov et al., 2001, and references therein). Of special interest are tetrazole compounds with activated methylene groups, which are very promising in fine organic synthesis (Dashkovskaya et al., 1990; Brekhov et al., 1992). In the light of this interest, we have prepared the title compound, (I), and present its crystal structure here. \sch
The molecule of (I) (Fig. 1) contains two 5-phenyltetrazole fragments, denoted A and B. The geometrical parameters of the tetrazole rings of the 5-phenyltetrazole fragments in the molecule of (I) are very similar (Table 1); corresponding bond distances and angles of the rings fall within the 3σ range. The tetrazole ring geometry is typical for 2,5-substituted tetrazoles (Cambridge Structural Database; Version 5.22 of October 2001; Allen & Kennard, 1993), with the following main features. The tetrazole rings are planar, to within 0.0016 (7) and 0.0027 (7) Å for fragments A and B, respectively. The N3—N4 bond is the shortest in the ring, while the N4—C5 bond is essentially larger than N1—C5. All the bond distances of the tetrazole rings, with the exception of N4—C5, lie within the narrow range of 1.3127 (16)–1.3333 (14) Å (fragment A) and 1.3131 (16)–1.3287 (13) Å (fragment B). This is indicative of more aromatic character of the ring in 2,5-substituted tetrazoles in comparison with 1-, 5- and 1,5-substituted tetrazoles.
The benzene rings in (I) are planar to within 0.0038 (11) and 0.0030 (9) Å for 5-phenyltetrazole fragments A and B, respectively. The bond distances and angles are consistent with those observed previously for the ring (Cambridge Structural Database; Version 5.22 of October 2001; Allen & Kennard, 1993).
The benzene and tetrazole rings in (I) were found to be non-coplanar in the 5-phenyltetrazole fragments, the dihedral angles between the rings being 2.45 (6) and 10.01 (9)° for fragments A and B, respectively.
With regard to the packing structure, the following features may be noted (Spek, 1999). There are no classical hydrogen bonds in the structure of (I), but weak intermolecular C1—H1B···N3Bi hydrogen bonds may be revealed [Table 2; symmetry code: (i) -x, 1 - y, -z]. These bonds are responsible for the formation of two-membered aggregates (Fig. 2).
Two types of intermolecular C—H···π interactions may be detected in the structure of (I) (Fig. 3 and Table 2). The first type corresponds to the interactions between atom H10A of one molecule and the B tetrazole π-ring of a second molecule at (1 - x, -y, -z). These interactions are characterized by the angle C10A—H10A···CgTz = 141.6 (12)° and the distance H10A···CgTz = 3.116 (16) Å (CgTz denotes the centroid of the tetrazole ring). These interactions form two-membered entities, as shown in Fig. 3.
Atom H9B of one molecule and the B benzene π-ring of another molecule at (-1/2 - x, y - 1/2, -1/2 - z) are involved in C—H···π interactions of the second type. These interactions are characterized by the angle C9B—H9B···CgBz = 140.1 (13)° and the distance H9B···CgBz = 2.877 (16) Å (CgBz denotes the centroid of the benzene ring). These interactions form chains extended along the b axis and link together the two-membered entities mentioned above, to form layers which are connected by C—H···N hydrogen bonds (Figs. 2 and 3).
As can be seen from Fig. 3, the crystal structure of (I) is also an object for investigations of πbenzene···πtetrazole stacking interactions.