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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008991/cv6113sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008991/cv6113Isup2.hkl
Contains datablock I

CCDC reference: 189414

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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








Computing details top

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
C16H14N4F(000) = 276
Mr = 262.32Dx = 1.304 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.3350 (4) ÅCell parameters from 7750 reflections
b = 5.0304 (8) Åθ = 1.5–27.5°
c = 9.5755 (13) ŵ = 0.08 mm1
β = 104.571 (4)°T = 150 K
V = 668.29 (14) Å3Plate, red
Z = 20.22 × 0.20 × 0.02 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1533 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode902 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.5°
φ and ω scansh = 1818
Absorption correction: multi-scan
Using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995)
k = 66
Tmin = 0.982, Tmax = 0.998l = 1212
7750 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-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 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
C11.23944 (10)0.1439 (3)0.72615 (15)0.0317 (4)
C21.22475 (11)0.0572 (3)0.81728 (16)0.0352 (4)
H21.16140.09170.82660.046*
C31.30064 (11)0.2077 (3)0.89451 (17)0.0407 (4)
H31.28950.34530.95630.053*
C41.39293 (12)0.1580 (3)0.88192 (19)0.0430 (4)
H41.44550.26020.93560.056*
C51.40830 (11)0.0401 (3)0.79137 (18)0.0433 (4)
H51.47170.07430.78250.056*
C61.33194 (10)0.1902 (3)0.71300 (17)0.0376 (4)
H61.34320.32550.65000.049*
C71.15525 (9)0.3103 (3)0.64484 (16)0.0361 (4)
H7A1.13420.42840.71380.047*
H7B1.17670.42400.57440.047*
C81.07163 (10)0.1455 (3)0.56663 (16)0.0324 (4)
N90.98662 (8)0.1817 (3)0.59775 (14)0.0415 (4)
N100.91304 (9)0.0318 (3)0.52888 (14)0.0429 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0311 (8)0.0346 (8)0.0290 (8)0.0043 (6)0.0067 (6)0.0072 (6)
C20.0316 (8)0.0425 (9)0.0325 (8)0.0050 (7)0.0100 (6)0.0031 (7)
C30.0443 (9)0.0414 (9)0.0341 (9)0.0049 (7)0.0057 (7)0.0005 (7)
C40.0371 (9)0.0455 (9)0.0407 (9)0.0034 (8)0.0010 (7)0.0035 (8)
C50.0303 (8)0.0487 (10)0.0511 (10)0.0042 (7)0.0107 (8)0.0057 (8)
C60.0352 (8)0.0396 (8)0.0391 (9)0.0051 (7)0.0115 (7)0.0005 (7)
C70.0338 (8)0.0359 (8)0.0391 (9)0.0014 (7)0.0099 (7)0.0012 (7)
C80.0294 (8)0.0395 (8)0.0280 (8)0.0049 (7)0.0067 (6)0.0032 (7)
N90.0295 (7)0.0544 (8)0.0397 (8)0.0016 (6)0.0068 (6)0.0096 (6)
N100.0295 (7)0.0571 (8)0.0418 (8)0.0009 (6)0.0084 (6)0.0126 (7)
Geometric parameters (Å, º) top
C1—C61.3829 (19)C5—H50.9500
C1—C21.386 (2)C6—H60.9500
C1—C71.5134 (19)C7—C81.4943 (19)
C2—C31.378 (2)C7—H7A0.9900
C2—H20.9500C7—H7B0.9900
C3—C41.381 (2)C8—N10i1.3348 (19)
C3—H30.9500C8—N91.3377 (19)
C4—C51.375 (2)N9—N101.3288 (17)
C4—H40.9500N10—C8i1.3348 (19)
C5—C61.385 (2)
C6—C1—C2118.77 (14)C1—C6—C5120.27 (14)
C6—C1—C7121.25 (13)C1—C6—H6119.9
C2—C1—C7119.98 (12)C5—C6—H6119.9
C3—C2—C1120.94 (13)C8—C7—C1112.74 (12)
C3—C2—H2119.5C8—C7—H7A109.0
C1—C2—H2119.5C1—C7—H7A109.0
C2—C3—C4119.87 (14)C8—C7—H7B109.0
C2—C3—H3120.1C1—C7—H7B109.0
C4—C3—H3120.1H7A—C7—H7B107.8
C5—C4—C3119.69 (15)N10i—C8—N9124.03 (13)
C5—C4—H4120.2N10i—C8—C7117.67 (12)
C3—C4—H4120.2N9—C8—C7118.29 (13)
C4—C5—C6120.45 (14)N10—N9—C8117.79 (12)
C4—C5—H5119.8N9—N10—C8i118.18 (12)
C6—C5—H5119.8
C1—C7—C8—N9122.01 (15)
Symmetry code: (i) x+2, y, z+1.
 

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