3,6-Diethyl-N,N'-bis(3-methyl­phenyl)-1,6-di­hydro-1,2,4,5-tetrazine-1,4-di­carbox­amide

The title compound, C₂₂H₂₆N₆O₂, was prepared from 3-tolyl isocyanate and 3,6-diethyl-1,6-di­hydro-s-tetrazine. The central six-membered ring has a boat conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.110
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3,6-Diethyl-N,N'-bis(3-methylphenyl)-1,6-dihydro-1,2,4,5-tetrazine- 1,4-dicarboxyamide

Crystal data

C22H26N6O2	Z = 2
Mr = 406.49	F(000) = 432
Triclinic, P1	Dx = 1.288 Mg m^−3
Hall symbol: -P 1	Melting point = 363–364 K
a = 8.425 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.357 (2) Å	Cell parameters from 25 reflections
c = 11.489 (2) Å	θ = 9.9–14.3°
α = 104.56 (2)°	µ = 0.09 mm^−1
β = 80.66 (2)°	T = 293 K
γ = 95.19 (3)°	Block, colourless
V = 1048.5 (6) Å^3	0.30 × 0.30 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	2707 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 25.2°, θmin = 1.9°
ω/2θ scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.975, Tmax = 0.983	l = −1→13
4371 measured reflections	3 standard reflections every 60 min
3762 independent reflections	intensity decay: 0.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.2187P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3762 reflections	Δρmax = 0.22 e Å^−3
276 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.07862 (17)	−0.08012 (10)	0.18620 (11)	0.0544 (3)
O2	0.41145 (15)	0.36852 (12)	0.54039 (11)	0.0550 (4)
N1	0.19904 (18)	0.04670 (12)	0.06810 (12)	0.0438 (3)
H1	0.2105	0.1225	0.0674	0.053*
N2	0.20689 (17)	0.29065 (13)	0.65972 (11)	0.0436 (3)
H2	0.1093	0.2607	0.6613	0.052*
N3	0.11635 (16)	0.12133 (11)	0.27287 (11)	0.0376 (3)
N4	0.18292 (16)	0.23501 (11)	0.25272 (11)	0.0370 (3)
N5	0.19549 (16)	0.27138 (12)	0.45707 (11)	0.0389 (3)
N6	0.04710 (15)	0.20384 (11)	0.47773 (11)	0.0363 (3)
C1	0.1928 (3)	−0.36540 (19)	−0.2120 (2)	0.0719 (6)
H1A	0.1664	−0.3955	−0.1399	0.108*
H1B	0.2716	−0.4150	−0.2683	0.108*
H1C	0.0975	−0.3682	−0.2487	0.108*
C2	0.2601 (2)	−0.23589 (16)	−0.17933 (16)	0.0491 (4)
C3	0.3876 (2)	−0.19474 (19)	−0.25334 (17)	0.0568 (5)
H3	0.4324	−0.2472	−0.3247	0.068*
C4	0.4489 (2)	−0.0761 (2)	−0.22181 (17)	0.0593 (5)
H4	0.5337	−0.0489	−0.2728	0.071*
C5	0.3858 (2)	0.00239 (18)	−0.11565 (16)	0.0508 (4)
H5	0.4288	0.0819	−0.0945	0.061*
C6	0.2581 (2)	−0.03764 (15)	−0.04054 (14)	0.0403 (4)
C7	0.1942 (2)	−0.15579 (15)	−0.07297 (15)	0.0439 (4)
H7	0.1067	−0.1820	−0.0235	0.053*
C8	0.12655 (19)	0.01979 (14)	0.17252 (14)	0.0387 (4)
C9	0.22775 (18)	0.30715 (14)	0.34718 (13)	0.0343 (3)
C10	0.01514 (18)	0.12486 (13)	0.38317 (13)	0.0336 (3)
C11	−0.1328 (2)	0.04228 (15)	0.38968 (16)	0.0440 (4)
H11A	−0.1008	−0.0392	0.3835	0.053*
H11B	−0.1864	0.0391	0.3202	0.053*
C12	−0.2512 (2)	0.0797 (2)	0.50395 (19)	0.0616 (5)
H12A	−0.1985	0.0861	0.5735	0.092*
H12B	−0.3393	0.0198	0.5038	0.092*
H12C	−0.2914	0.1572	0.5073	0.092*
C13	0.2996 (2)	0.43096 (14)	0.34029 (14)	0.0396 (4)
H13A	0.3143	0.4367	0.2563	0.048*
H13B	0.4051	0.4409	0.3661	0.048*
C14	0.1984 (3)	0.53342 (16)	0.41736 (19)	0.0588 (5)
H14A	0.0953	0.5264	0.3902	0.088*
H14B	0.2518	0.6101	0.4102	0.088*
H14C	0.1838	0.5289	0.5008	0.088*
C15	0.2810 (2)	0.31588 (14)	0.55471 (14)	0.0389 (4)
C16	0.2770 (2)	0.30965 (14)	0.76725 (14)	0.0385 (4)
C17	0.4422 (2)	0.31142 (15)	0.76542 (15)	0.0434 (4)
H17	0.5100	0.3011	0.6915	0.052*
C18	0.5082 (2)	0.32825 (15)	0.87179 (15)	0.0458 (4)
C19	0.4054 (3)	0.34149 (17)	0.98023 (16)	0.0538 (5)
H19	0.4474	0.3528	1.0525	0.065*
C20	0.2414 (3)	0.33812 (19)	0.98236 (16)	0.0577 (5)
H20	0.1737	0.3465	1.0561	0.069*
C21	0.1758 (2)	0.32243 (17)	0.87651 (15)	0.0486 (4)
H21	0.0647	0.3205	0.8788	0.058*
C22	0.6874 (2)	0.3290 (2)	0.8679 (2)	0.0661 (6)
H22A	0.7164	0.3746	0.9446	0.099*
H22B	0.7407	0.3660	0.8046	0.099*
H22C	0.7196	0.2468	0.8521	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0757 (9)	0.0349 (6)	0.0460 (7)	−0.0008 (6)	−0.0024 (6)	0.0030 (5)
O2	0.0540 (8)	0.0715 (8)	0.0417 (7)	−0.0255 (6)	−0.0168 (6)	0.0213 (6)
N1	0.0580 (9)	0.0365 (7)	0.0334 (7)	0.0033 (6)	−0.0051 (6)	0.0027 (6)
N2	0.0445 (8)	0.0554 (8)	0.0296 (7)	−0.0108 (6)	−0.0085 (6)	0.0104 (6)
N3	0.0470 (8)	0.0323 (7)	0.0313 (7)	−0.0020 (6)	−0.0063 (6)	0.0044 (5)
N4	0.0446 (8)	0.0344 (7)	0.0312 (7)	−0.0016 (6)	−0.0050 (6)	0.0077 (5)
N5	0.0440 (8)	0.0427 (7)	0.0289 (7)	−0.0117 (6)	−0.0082 (6)	0.0098 (6)
N6	0.0366 (7)	0.0385 (7)	0.0332 (7)	−0.0050 (5)	−0.0055 (5)	0.0095 (6)
C1	0.0924 (17)	0.0541 (12)	0.0596 (13)	0.0132 (11)	−0.0166 (12)	−0.0108 (10)
C2	0.0571 (11)	0.0496 (10)	0.0398 (9)	0.0178 (8)	−0.0155 (8)	−0.0014 (8)
C3	0.0584 (12)	0.0696 (13)	0.0387 (10)	0.0277 (10)	−0.0061 (9)	−0.0016 (9)
C4	0.0500 (11)	0.0814 (15)	0.0447 (10)	0.0143 (10)	0.0007 (8)	0.0131 (10)
C5	0.0507 (11)	0.0555 (11)	0.0443 (10)	0.0019 (8)	−0.0085 (8)	0.0080 (8)
C6	0.0442 (9)	0.0449 (9)	0.0311 (8)	0.0094 (7)	−0.0101 (7)	0.0022 (7)
C7	0.0476 (10)	0.0468 (10)	0.0356 (9)	0.0075 (7)	−0.0096 (7)	0.0030 (7)
C8	0.0443 (9)	0.0348 (9)	0.0356 (9)	0.0028 (7)	−0.0115 (7)	0.0017 (7)
C9	0.0361 (8)	0.0372 (8)	0.0283 (7)	0.0011 (6)	−0.0038 (6)	0.0064 (6)
C10	0.0369 (8)	0.0332 (8)	0.0325 (8)	0.0033 (6)	−0.0085 (6)	0.0088 (6)
C11	0.0426 (9)	0.0422 (9)	0.0472 (10)	−0.0059 (7)	−0.0127 (7)	0.0094 (7)
C12	0.0449 (10)	0.0732 (13)	0.0599 (12)	−0.0117 (9)	−0.0003 (9)	0.0135 (10)
C13	0.0450 (9)	0.0395 (9)	0.0319 (8)	−0.0047 (7)	−0.0013 (7)	0.0091 (7)
C14	0.0624 (12)	0.0423 (10)	0.0633 (12)	−0.0007 (9)	0.0077 (10)	0.0092 (9)
C15	0.0464 (10)	0.0384 (8)	0.0314 (8)	−0.0062 (7)	−0.0095 (7)	0.0079 (7)
C16	0.0501 (10)	0.0355 (8)	0.0292 (8)	−0.0069 (7)	−0.0082 (7)	0.0080 (6)
C17	0.0485 (10)	0.0484 (9)	0.0335 (8)	0.0022 (7)	−0.0037 (7)	0.0114 (7)
C18	0.0571 (11)	0.0423 (9)	0.0418 (9)	0.0031 (8)	−0.0140 (8)	0.0127 (7)
C19	0.0704 (13)	0.0605 (11)	0.0336 (9)	0.0012 (9)	−0.0172 (9)	0.0115 (8)
C20	0.0677 (13)	0.0738 (13)	0.0295 (9)	0.0000 (10)	−0.0023 (8)	0.0129 (9)
C21	0.0485 (10)	0.0579 (11)	0.0369 (9)	−0.0064 (8)	−0.0043 (7)	0.0113 (8)
C22	0.0597 (13)	0.0831 (15)	0.0653 (13)	0.0114 (11)	−0.0207 (10)	0.0257 (11)

Geometric parameters (Å, º)

O1—C8	1.2089 (19)	C7—H7	0.9300
O2—C15	1.210 (2)	C9—C13	1.495 (2)
N1—C8	1.349 (2)	C10—C11	1.494 (2)
N1—C6	1.417 (2)	C11—C12	1.507 (3)
N1—H1	0.8600	C11—H11A	0.9700
N2—C15	1.351 (2)	C11—H11B	0.9700
N2—C16	1.415 (2)	C12—H12A	0.9599
N2—H2	0.8600	C12—H12B	0.9599
N3—C10	1.402 (2)	C12—H12C	0.9599
N3—C8	1.4084 (19)	C13—C14	1.510 (2)
N3—N4	1.418 (2)	C13—H13A	0.9700
N4—C9	1.273 (2)	C13—H13B	0.9700
N5—C15	1.394 (2)	C14—H14A	0.9599
N5—C9	1.400 (2)	C14—H14B	0.9599
N5—N6	1.425 (2)	C14—H14C	0.9599
N6—C10	1.272 (2)	C16—C21	1.381 (2)
C1—C2	1.506 (3)	C16—C17	1.387 (3)
C1—H1A	0.9599	C17—C18	1.387 (2)
C1—H1B	0.9599	C17—H17	0.9300
C1—H1C	0.9599	C18—C19	1.380 (3)
C2—C3	1.381 (3)	C18—C22	1.503 (3)
C2—C7	1.393 (2)	C19—C20	1.375 (3)
C3—C4	1.380 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.381 (3)
C4—C5	1.376 (3)	C20—H20	0.9300
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.384 (2)	C22—H22A	0.9599
C5—H5	0.9300	C22—H22B	0.9599
C6—C7	1.383 (2)	C22—H22C	0.9599
C8—N1—C6	126.42 (14)	C12—C11—H11A	108.7
C8—N1—H1	116.8	C10—C11—H11B	108.7
C6—N1—H1	116.8	C12—C11—H11B	108.7
C15—N2—C16	125.20 (14)	H11A—C11—H11B	107.6
C15—N2—H2	117.4	C11—C12—H12A	109.5
C16—N2—H2	117.4	C11—C12—H12B	109.5
C10—N3—C8	124.34 (13)	H12A—C12—H12B	109.5
C10—N3—N4	116.4 (1)	C11—C12—H12C	109.5
C8—N3—N4	117.63 (12)	H12A—C12—H12C	109.5
C9—N4—N3	113.24 (12)	H12B—C12—H12C	109.5
C15—N5—C9	124.54 (13)	C9—C13—C14	113.56 (14)
C15—N5—N6	117.86 (12)	C9—C13—H13A	108.9
C9—N5—N6	116.4 (1)	C14—C13—H13A	108.9
C10—N6—N5	112.74 (12)	C9—C13—H13B	108.9
C2—C1—H1A	109.5	C14—C13—H13B	108.9
C2—C1—H1B	109.5	H13A—C13—H13B	107.7
H1A—C1—H1B	109.5	C13—C14—H14A	109.5
C2—C1—H1C	109.5	C13—C14—H14B	109.5
H1A—C1—H1C	109.5	H14A—C14—H14B	109.5
H1B—C1—H1C	109.5	C13—C14—H14C	109.5
C3—C2—C7	119.06 (17)	H14A—C14—H14C	109.5
C3—C2—C1	120.90 (17)	H14B—C14—H14C	109.5
C7—C2—C1	120.04 (18)	O2—C15—N2	125.75 (15)
C4—C3—C2	120.28 (17)	O2—C15—N5	120.38 (14)
C4—C3—H3	119.9	N2—C15—N5	113.84 (14)
C2—C3—H3	119.9	C21—C16—C17	119.62 (15)
C5—C4—C3	120.67 (19)	C21—C16—N2	118.20 (15)
C5—C4—H4	119.7	C17—C16—N2	122.15 (14)
C3—C4—H4	119.7	C18—C17—C16	121.17 (16)
C4—C5—C6	119.66 (18)	C18—C17—H17	119.4
C4—C5—H5	120.2	C16—C17—H17	119.4
C6—C5—H5	120.2	C19—C18—C17	118.49 (17)
C7—C6—C5	119.86 (16)	C19—C18—C22	121.09 (17)
C7—C6—N1	122.92 (16)	C17—C18—C22	120.40 (17)
C5—C6—N1	117.22 (15)	C20—C19—C18	120.57 (17)
C6—C7—C2	120.43 (17)	C20—C19—H19	119.7
C6—C7—H7	119.8	C18—C19—H19	119.7
C2—C7—H7	119.8	C19—C20—C21	120.94 (17)
O1—C8—N1	126.43 (14)	C19—C20—H20	119.5
O1—C8—N3	120.10 (15)	C21—C20—H20	119.5
N1—C8—N3	113.40 (14)	C16—C21—C20	119.21 (18)
N4—C9—N5	118.44 (13)	C16—C21—H21	120.4
N4—C9—C13	119.45 (14)	C20—C21—H21	120.4
N5—C9—C13	121.88 (13)	C18—C22—H22A	109.5
N6—C10—N3	118.82 (13)	C18—C22—H22B	109.5
N6—C10—C11	119.94 (14)	H22A—C22—H22B	109.5
N3—C10—C11	121.16 (13)	C18—C22—H22C	109.5
C10—C11—C12	114.40 (14)	H22A—C22—H22C	109.5
C10—C11—H11A	108.7	H22B—C22—H22C	109.5
C10—N3—N4—C9	40.5 (2)	N5—N6—C10—N3	−5.61 (19)
C8—N3—N4—C9	−153.41 (14)	N5—N6—C10—C11	177.53 (13)
C15—N5—N6—C10	−150.58 (15)	C8—N3—C10—N6	159.68 (15)
C9—N5—N6—C10	41.3 (2)	N4—N3—C10—N6	−35.3 (2)
C7—C2—C3—C4	0.3 (3)	C8—N3—C10—C11	−23.5 (2)
C1—C2—C3—C4	−179.52 (19)	N4—N3—C10—C11	141.52 (14)
C2—C3—C4—C5	1.0 (3)	N6—C10—C11—C12	13.0 (2)
C3—C4—C5—C6	−0.9 (3)	N3—C10—C11—C12	−163.83 (16)
C4—C5—C6—C7	−0.4 (3)	N4—C9—C13—C14	114.72 (18)
C4—C5—C6—N1	179.43 (17)	N5—C9—C13—C14	−59.8 (2)
C8—N1—C6—C7	27.9 (3)	C16—N2—C15—O2	−7.4 (3)
C8—N1—C6—C5	−151.85 (17)	C16—N2—C15—N5	170.45 (15)
C5—C6—C7—C2	1.6 (2)	C9—N5—C15—O2	−16.6 (3)
N1—C6—C7—C2	−178.18 (15)	N6—N5—C15—O2	176.30 (15)
C3—C2—C7—C6	−1.5 (3)	C9—N5—C15—N2	165.48 (14)
C1—C2—C7—C6	178.24 (17)	N6—N5—C15—N2	−1.6 (2)
C6—N1—C8—O1	−11.6 (3)	C15—N2—C16—C21	156.87 (16)
C6—N1—C8—N3	165.33 (15)	C15—N2—C16—C17	−25.4 (3)
C10—N3—C8—O1	−18.7 (2)	C21—C16—C17—C18	−1.3 (3)
N4—N3—C8—O1	176.42 (14)	N2—C16—C17—C18	−178.96 (15)
C10—N3—C8—N1	164.13 (14)	C16—C17—C18—C19	1.0 (3)
N4—N3—C8—N1	−0.7 (2)	C16—C17—C18—C22	179.55 (17)
N3—N4—C9—N5	−5.0 (2)	C17—C18—C19—C20	−0.1 (3)
N3—N4—C9—C13	−179.65 (13)	C22—C18—C19—C20	−178.63 (19)
C15—N5—C9—N4	156.59 (15)	C18—C19—C20—C21	−0.5 (3)
N6—N5—C9—N4	−36.1 (2)	C17—C16—C21—C20	0.7 (3)
C15—N5—C9—C13	−28.9 (2)	N2—C16—C21—C20	178.45 (17)
N6—N5—C9—C13	138.44 (14)	C19—C20—C21—C16	0.2 (3)