Buy article online - an online subscription or single-article purchase is required to access this article.
In trans-3,6-dibenzyl-1,2,4,5-tetrazine, C16H14N4, with crystallographic inversion symmetry, there is an angle of 84.73 (4)° between the phenyl and tetrazine planes. Close contacts between H atoms on each phenyl group with phenyl rings in adjacent molecules (3.353 and 3.382 Å) give rise to weak layers parallel to the bc plane, but there are no intermolecular π interactions.
Supporting information
CCDC reference: 189414
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.052
- wR factor = 0.141
- Data-to-parameter ratio = 16.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
trans-3,6-Dibenzyl-1,2,4,5-tetrazine
top
Crystal data top
C16H14N4 | F(000) = 276 |
Mr = 262.32 | Dx = 1.304 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.3350 (4) Å | Cell parameters from 7750 reflections |
b = 5.0304 (8) Å | θ = 1.5–27.5° |
c = 9.5755 (13) Å | µ = 0.08 mm−1 |
β = 104.571 (4)° | T = 150 K |
V = 668.29 (14) Å3 | Plate, red |
Z = 2 | 0.22 × 0.20 × 0.02 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 1533 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 902 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 1.5° |
φ and ω scans | h = −18→18 |
Absorption correction: multi-scan Using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995) | k = −6→6 |
Tmin = 0.982, Tmax = 0.998 | l = −12→12 |
7750 measured reflections | |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0808P)2] where P = (Fo2 + 2Fc2)/3 |
1533 reflections | (Δ/σ)max = 0.002 |
91 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Special details top
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the
entire data set is used to refine the cell, which is indexed from all observed
reflections in a 10 degree phi range. |
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. Hydrogen atoms were placed on calculated positions and allowed to ride on the
adjacent carbon atom during refinement. Isotropic displacement parameters were
constrained to be 1.3 times the U(eq) of the adjacent carbon atom. 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 | 1.23944 (10) | 0.1439 (3) | 0.72615 (15) | 0.0317 (4) | |
C2 | 1.22475 (11) | −0.0572 (3) | 0.81728 (16) | 0.0352 (4) | |
H2 | 1.1614 | −0.0917 | 0.8266 | 0.046* | |
C3 | 1.30064 (11) | −0.2077 (3) | 0.89451 (17) | 0.0407 (4) | |
H3 | 1.2895 | −0.3453 | 0.9563 | 0.053* | |
C4 | 1.39293 (12) | −0.1580 (3) | 0.88192 (19) | 0.0430 (4) | |
H4 | 1.4455 | −0.2602 | 0.9356 | 0.056* | |
C5 | 1.40830 (11) | 0.0401 (3) | 0.79137 (18) | 0.0433 (4) | |
H5 | 1.4717 | 0.0743 | 0.7825 | 0.056* | |
C6 | 1.33194 (10) | 0.1902 (3) | 0.71300 (17) | 0.0376 (4) | |
H6 | 1.3432 | 0.3255 | 0.6500 | 0.049* | |
C7 | 1.15525 (9) | 0.3103 (3) | 0.64484 (16) | 0.0361 (4) | |
H7A | 1.1342 | 0.4284 | 0.7138 | 0.047* | |
H7B | 1.1767 | 0.4240 | 0.5744 | 0.047* | |
C8 | 1.07163 (10) | 0.1455 (3) | 0.56663 (16) | 0.0324 (4) | |
N9 | 0.98662 (8) | 0.1817 (3) | 0.59775 (14) | 0.0415 (4) | |
N10 | 0.91304 (9) | 0.0318 (3) | 0.52888 (14) | 0.0429 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0311 (8) | 0.0346 (8) | 0.0290 (8) | −0.0043 (6) | 0.0067 (6) | −0.0072 (6) |
C2 | 0.0316 (8) | 0.0425 (9) | 0.0325 (8) | −0.0050 (7) | 0.0100 (6) | −0.0031 (7) |
C3 | 0.0443 (9) | 0.0414 (9) | 0.0341 (9) | −0.0049 (7) | 0.0057 (7) | −0.0005 (7) |
C4 | 0.0371 (9) | 0.0455 (9) | 0.0407 (9) | 0.0034 (8) | −0.0010 (7) | −0.0035 (8) |
C5 | 0.0303 (8) | 0.0487 (10) | 0.0511 (10) | −0.0042 (7) | 0.0107 (8) | −0.0057 (8) |
C6 | 0.0352 (8) | 0.0396 (8) | 0.0391 (9) | −0.0051 (7) | 0.0115 (7) | 0.0005 (7) |
C7 | 0.0338 (8) | 0.0359 (8) | 0.0391 (9) | −0.0014 (7) | 0.0099 (7) | −0.0012 (7) |
C8 | 0.0294 (8) | 0.0395 (8) | 0.0280 (8) | 0.0049 (7) | 0.0067 (6) | 0.0032 (7) |
N9 | 0.0295 (7) | 0.0544 (8) | 0.0397 (8) | 0.0016 (6) | 0.0068 (6) | −0.0096 (6) |
N10 | 0.0295 (7) | 0.0571 (8) | 0.0418 (8) | −0.0009 (6) | 0.0084 (6) | −0.0126 (7) |
Geometric parameters (Å, º) top
C1—C6 | 1.3829 (19) | C5—H5 | 0.9500 |
C1—C2 | 1.386 (2) | C6—H6 | 0.9500 |
C1—C7 | 1.5134 (19) | C7—C8 | 1.4943 (19) |
C2—C3 | 1.378 (2) | C7—H7A | 0.9900 |
C2—H2 | 0.9500 | C7—H7B | 0.9900 |
C3—C4 | 1.381 (2) | C8—N10i | 1.3348 (19) |
C3—H3 | 0.9500 | C8—N9 | 1.3377 (19) |
C4—C5 | 1.375 (2) | N9—N10 | 1.3288 (17) |
C4—H4 | 0.9500 | N10—C8i | 1.3348 (19) |
C5—C6 | 1.385 (2) | | |
| | | |
C6—C1—C2 | 118.77 (14) | C1—C6—C5 | 120.27 (14) |
C6—C1—C7 | 121.25 (13) | C1—C6—H6 | 119.9 |
C2—C1—C7 | 119.98 (12) | C5—C6—H6 | 119.9 |
C3—C2—C1 | 120.94 (13) | C8—C7—C1 | 112.74 (12) |
C3—C2—H2 | 119.5 | C8—C7—H7A | 109.0 |
C1—C2—H2 | 119.5 | C1—C7—H7A | 109.0 |
C2—C3—C4 | 119.87 (14) | C8—C7—H7B | 109.0 |
C2—C3—H3 | 120.1 | C1—C7—H7B | 109.0 |
C4—C3—H3 | 120.1 | H7A—C7—H7B | 107.8 |
C5—C4—C3 | 119.69 (15) | N10i—C8—N9 | 124.03 (13) |
C5—C4—H4 | 120.2 | N10i—C8—C7 | 117.67 (12) |
C3—C4—H4 | 120.2 | N9—C8—C7 | 118.29 (13) |
C4—C5—C6 | 120.45 (14) | N10—N9—C8 | 117.79 (12) |
C4—C5—H5 | 119.8 | N9—N10—C8i | 118.18 (12) |
C6—C5—H5 | 119.8 | | |
| | | |
C1—C7—C8—N9 | 122.01 (15) | | |
Symmetry code: (i) −x+2, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.