Slight pyramidalization at the four N atoms leads to a twist boat conformation for the tetrazinane ring of the title compound, C
4H
8N
4O
2. In the crystal structure, the tetrazinane-3,6-dione molecules are disordered over two conformations with opposite ring puckerings, and are linked into two-dimensional sheets by N—H
O hydrogen bonding.
Supporting information
CCDC reference: 259855
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (Please check) = 0.000 Å
- R factor = 0.038
- wR factor = 0.110
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT301_ALERT_3_B Main Residue Disorder ......................... 50.00 Perc.
Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
1,5-Dimethyl-1,2,4,5-tetrazinane-3,6-dione
top
Crystal data top
C4H8N4O2 | F(000) = 304 |
Mr = 144.14 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5956 reflections |
a = 7.6861 (3) Å | θ = 1.0–27.5° |
b = 10.8182 (4) Å | µ = 0.12 mm−1 |
c = 7.8238 (3) Å | T = 150 K |
β = 91.4690 (16)° | Block, colourless |
V = 650.33 (4) Å3 | 0.27 × 0.27 × 0.18 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 1146 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.046 |
Graphite monochromator | θmax = 27.5°, θmin = 2.7° |
φ and ω scans | h = −9→9 |
6507 measured reflections | k = −14→13 |
1482 independent reflections | l = −9→10 |
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)] = 0.038 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0585P)2 + 0.0925P] where P = (Fo2 + 2Fc2)/3 |
1482 reflections | (Δ/σ)max = 0.001 |
132 parameters | Δρmax = 0.16 e Å−3 |
32 restraints | Δρmin = −0.20 e Å−3 |
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 | Occ. (<1) |
N1 | 0.9149 (3) | 0.1668 (2) | 0.2447 (3) | 0.0312 (7) | 0.729 (9) |
N2 | 0.8922 (2) | 0.05534 (19) | 0.3408 (3) | 0.0303 (5) | 0.729 (9) |
H2 | 0.963 (2) | −0.0056 (15) | 0.317 (3) | 0.036* | 0.729 (9) |
C3 | 0.72872 (15) | 0.02781 (11) | 0.38972 (16) | 0.0267 (3) | 0.729 (9) |
N4 | 0.6145 (2) | 0.12321 (16) | 0.3803 (3) | 0.0288 (5) | 0.729 (9) |
H4 | 0.516 (2) | 0.1101 (16) | 0.441 (3) | 0.035* | 0.729 (9) |
N5 | 0.6896 (3) | 0.2437 (2) | 0.3992 (3) | 0.0320 (6) | 0.729 (9) |
C6 | 0.82944 (17) | 0.26960 (11) | 0.30117 (17) | 0.0285 (3) | 0.729 (9) |
C7 | 1.0889 (7) | 0.1768 (6) | 0.1758 (12) | 0.0371 (10) | 0.729 (9) |
H7A | 1.0998 | 0.2557 | 0.1154 | 0.056* | 0.729 (9) |
H7B | 1.1081 | 0.1086 | 0.0961 | 0.056* | 0.729 (9) |
H7C | 1.1757 | 0.1729 | 0.2695 | 0.056* | 0.729 (9) |
C8 | 0.5615 (7) | 0.3397 (4) | 0.4303 (9) | 0.0338 (8) | 0.729 (9) |
H8A | 0.6199 | 0.4200 | 0.4391 | 0.051* | 0.729 (9) |
H8B | 0.5026 | 0.3221 | 0.5372 | 0.051* | 0.729 (9) |
H8C | 0.4757 | 0.3415 | 0.3355 | 0.051* | 0.729 (9) |
O9 | 0.6916 (7) | −0.0774 (3) | 0.4407 (8) | 0.0283 (9) | 0.729 (9) |
O10 | 0.8716 (9) | 0.3756 (3) | 0.2614 (9) | 0.0357 (11) | 0.729 (9) |
N1B | 0.9361 (9) | 0.1715 (6) | 0.2909 (12) | 0.0312 (7) | 0.271 (9) |
N2B | 0.8561 (8) | 0.0531 (6) | 0.2825 (8) | 0.0303 (5) | 0.271 (9) |
H2B | 0.934 (4) | −0.0095 (19) | 0.262 (6) | 0.036* | 0.271 (9) |
C3B | 0.72872 (15) | 0.02781 (11) | 0.38972 (16) | 0.0267 (3) | 0.271 (9) |
N4B | 0.6426 (7) | 0.1328 (5) | 0.4453 (7) | 0.0288 (5) | 0.271 (9) |
H4B | 0.541 (4) | 0.117 (2) | 0.493 (6) | 0.035* | 0.271 (9) |
N5B | 0.6597 (8) | 0.2434 (6) | 0.3465 (10) | 0.0320 (6) | 0.271 (9) |
C6B | 0.82944 (17) | 0.26960 (11) | 0.30117 (17) | 0.0285 (3) | 0.271 (9) |
C7B | 1.097 (2) | 0.1774 (17) | 0.195 (4) | 0.0371 (10) | 0.271 (9) |
H7D | 1.1390 | 0.2629 | 0.1926 | 0.056* | 0.271 (9) |
H7E | 1.0738 | 0.1489 | 0.0773 | 0.056* | 0.271 (9) |
H7F | 1.1852 | 0.1244 | 0.2496 | 0.056* | 0.271 (9) |
C8B | 0.552 (2) | 0.3440 (12) | 0.409 (3) | 0.0338 (8) | 0.271 (9) |
H8D | 0.5562 | 0.4138 | 0.3294 | 0.051* | 0.271 (9) |
H8E | 0.5955 | 0.3701 | 0.5220 | 0.051* | 0.271 (9) |
H8F | 0.4314 | 0.3154 | 0.4173 | 0.051* | 0.271 (9) |
O9B | 0.673 (2) | −0.0775 (9) | 0.415 (2) | 0.0283 (9) | 0.271 (9) |
O10B | 0.883 (3) | 0.3769 (9) | 0.290 (3) | 0.0357 (11) | 0.271 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0271 (9) | 0.0244 (6) | 0.0427 (19) | 0.0003 (5) | 0.0102 (10) | 0.0096 (8) |
N2 | 0.0279 (10) | 0.0202 (6) | 0.0435 (14) | 0.0017 (7) | 0.0118 (9) | 0.0052 (9) |
C3 | 0.0255 (6) | 0.0238 (6) | 0.0308 (7) | −0.0011 (5) | 0.0032 (5) | 0.0005 (5) |
N4 | 0.0227 (8) | 0.0232 (7) | 0.0407 (13) | −0.0003 (6) | 0.0070 (8) | 0.0048 (8) |
N5 | 0.0324 (10) | 0.0184 (6) | 0.0457 (17) | 0.0005 (6) | 0.0134 (9) | 0.0011 (9) |
C6 | 0.0308 (6) | 0.0236 (6) | 0.0311 (7) | −0.0015 (5) | 0.0045 (5) | 0.0021 (5) |
C7 | 0.0296 (9) | 0.0318 (7) | 0.051 (3) | −0.0004 (6) | 0.0133 (13) | 0.0077 (9) |
C8 | 0.0352 (9) | 0.0260 (8) | 0.041 (2) | 0.0060 (6) | 0.0074 (13) | 0.0008 (8) |
O9 | 0.0250 (14) | 0.0216 (5) | 0.039 (2) | −0.0013 (5) | 0.0050 (13) | 0.0031 (6) |
O10 | 0.0417 (11) | 0.0227 (5) | 0.043 (3) | −0.0039 (4) | 0.0113 (15) | 0.0037 (7) |
N1B | 0.0271 (9) | 0.0244 (6) | 0.0427 (19) | 0.0003 (5) | 0.0102 (10) | 0.0096 (8) |
N2B | 0.0279 (10) | 0.0202 (6) | 0.0435 (14) | 0.0017 (7) | 0.0118 (9) | 0.0052 (9) |
C3B | 0.0255 (6) | 0.0238 (6) | 0.0308 (7) | −0.0011 (5) | 0.0032 (5) | 0.0005 (5) |
N4B | 0.0227 (8) | 0.0232 (7) | 0.0407 (13) | −0.0003 (6) | 0.0070 (8) | 0.0048 (8) |
N5B | 0.0324 (10) | 0.0184 (6) | 0.0457 (17) | 0.0005 (6) | 0.0134 (9) | 0.0011 (9) |
C6B | 0.0308 (6) | 0.0236 (6) | 0.0311 (7) | −0.0015 (5) | 0.0045 (5) | 0.0021 (5) |
C7B | 0.0296 (9) | 0.0318 (7) | 0.051 (3) | −0.0004 (6) | 0.0133 (13) | 0.0077 (9) |
C8B | 0.0352 (9) | 0.0260 (8) | 0.041 (2) | 0.0060 (6) | 0.0074 (13) | 0.0008 (8) |
O9B | 0.0250 (14) | 0.0216 (5) | 0.039 (2) | −0.0013 (5) | 0.0050 (13) | 0.0031 (6) |
O10B | 0.0417 (11) | 0.0227 (5) | 0.043 (3) | −0.0039 (4) | 0.0113 (15) | 0.0037 (7) |
Geometric parameters (Å, º) top
N1—N2 | 1.434 (3) | C8—H8A | 0.9800 |
N1—C7 | 1.459 (3) | C8—H8B | 0.9800 |
N2—C3 | 1.356 (2) | C8—H8C | 0.9800 |
C3—N4 | 1.356 (2) | N1B—N2B | 1.422 (7) |
C3—O9 | 1.242 (3) | N1B—C7B | 1.465 (7) |
N4—N5 | 1.432 (2) | N2B—H2B | 0.921 (16) |
N5—C6 | 1.365 (2) | N4B—N5B | 1.433 (6) |
N5—C8 | 1.456 (3) | N4B—H4B | 0.886 (16) |
C6—N1 | 1.370 (3) | N5B—C8B | 1.459 (7) |
C6—O10 | 1.234 (3) | C7B—H7D | 0.9800 |
N2—H2 | 0.880 (14) | C7B—H7E | 0.9800 |
N4—H4 | 0.916 (14) | C7B—H7F | 0.9800 |
C7—H7A | 0.9800 | C8B—H8D | 0.9800 |
C7—H7B | 0.9800 | C8B—H8E | 0.9800 |
C7—H7C | 0.9800 | C8B—H8F | 0.9800 |
| | | |
C6—N1—N2 | 116.6 (2) | N5—N4—H4 | 115.1 (12) |
C6—N1—C7 | 120.7 (3) | N2B—N1B—C7B | 112.6 (9) |
N2—N1—C7 | 112.4 (3) | N1B—N2B—H2B | 112.8 (18) |
N1—N2—C3 | 117.30 (18) | N5B—N4B—H4B | 118.6 (19) |
N2—C3—N4 | 114.89 (14) | N4B—N5B—C8B | 112.4 (8) |
N2—C3—O9 | 120.9 (3) | N1B—C7B—H7D | 109.5 |
N4—C3—O9 | 124.2 (3) | N1B—C7B—H7E | 109.5 |
C3—N4—N5 | 115.38 (17) | H7D—C7B—H7E | 109.5 |
N4—N5—C6 | 116.72 (19) | N1B—C7B—H7F | 109.5 |
N4—N5—C8 | 113.2 (3) | H7D—C7B—H7F | 109.5 |
C6—N5—C8 | 119.6 (3) | H7E—C7B—H7F | 109.5 |
N5—C6—N1 | 113.93 (16) | N5B—C8B—H8D | 109.5 |
N5—C6—O10 | 123.2 (3) | N5B—C8B—H8E | 109.5 |
N1—C6—O10 | 122.8 (3) | H8D—C8B—H8E | 109.5 |
C3—N2—H2 | 118.7 (12) | N5B—C8B—H8F | 109.5 |
N1—N2—H2 | 115.8 (12) | H8D—C8B—H8F | 109.5 |
C3—N4—H4 | 113.4 (11) | H8E—C8B—H8F | 109.5 |
| | | |
C6—N1—N2—C3 | 43.8 (3) | N4—N5—C6—O10 | 155.8 (4) |
C7—N1—N2—C3 | −170.7 (4) | C8—N5—C6—O10 | 13.4 (6) |
N1—N2—C3—O9 | 164.8 (4) | N4—N5—C6—N1 | −21.6 (2) |
N1—N2—C3—N4 | −16.1 (2) | C8—N5—C6—N1 | −164.0 (4) |
O9—C3—N4—N5 | 151.4 (4) | N2—N1—C6—O10 | 160.3 (4) |
N2—C3—N4—N5 | −27.8 (2) | C7—N1—C6—O10 | 17.9 (7) |
C3—N4—N5—C6 | 49.5 (3) | N2—N1—C6—N5 | −22.3 (3) |
C3—N4—N5—C8 | −165.8 (3) | C7—N1—C6—N5 | −164.7 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O10i | 0.88 (1) | 1.92 (2) | 2.791 (4) | 172 (2) |
N4—H4···O9ii | 0.92 (1) | 1.90 (2) | 2.813 (6) | 177 (2) |
N2—H2···O10Bi | 0.88 (1) | 1.94 (2) | 2.802 (11) | 166 (2) |
N4—H4···O9Bii | 0.92 (1) | 1.89 (2) | 2.805 (16) | 174 (2) |
N2B—H2B···O10i | 0.92 (2) | 1.96 (2) | 2.867 (8) | 170 (4) |
N2B—H2B···O10Bi | 0.92 (2) | 1.92 (2) | 2.835 (13) | 172 (2) |
N4B—H4B···O9ii | 0.89 (2) | 1.93 (2) | 2.805 (8) | 171 (5) |
N4B—H4B···O9Bii | 0.89 (2) | 1.87 (2) | 2.750 (16) | 177 (4) |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, −y, −z+1. |