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Slight pyramidalization at the four N atoms leads to a twist boat conformation for the tetrazinane ring of the title compound, C4H8N4O2. 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030557/rz6023sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030557/rz6023Isup2.hkl
Contains datablock I

CCDC reference: 259855

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](Please check) = 0.000 Å
  • R factor = 0.038
  • wR factor = 0.110
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

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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

Computing details top

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
C4H8N4O2F(000) = 304
Mr = 144.14Dx = 1.472 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5956 reflections
a = 7.6861 (3) Åθ = 1.0–27.5°
b = 10.8182 (4) ŵ = 0.12 mm1
c = 7.8238 (3) ÅT = 150 K
β = 91.4690 (16)°Block, colourless
V = 650.33 (4) Å30.27 × 0.27 × 0.18 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1146 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.046
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
φ and ω scansh = 99
6507 measured reflectionsk = 1413
1482 independent reflectionsl = 910
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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.110H-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 parametersΔρmax = 0.16 e Å3
32 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/UeqOcc. (<1)
N10.9149 (3)0.1668 (2)0.2447 (3)0.0312 (7)0.729 (9)
N20.8922 (2)0.05534 (19)0.3408 (3)0.0303 (5)0.729 (9)
H20.963 (2)0.0056 (15)0.317 (3)0.036*0.729 (9)
C30.72872 (15)0.02781 (11)0.38972 (16)0.0267 (3)0.729 (9)
N40.6145 (2)0.12321 (16)0.3803 (3)0.0288 (5)0.729 (9)
H40.516 (2)0.1101 (16)0.441 (3)0.035*0.729 (9)
N50.6896 (3)0.2437 (2)0.3992 (3)0.0320 (6)0.729 (9)
C60.82944 (17)0.26960 (11)0.30117 (17)0.0285 (3)0.729 (9)
C71.0889 (7)0.1768 (6)0.1758 (12)0.0371 (10)0.729 (9)
H7A1.09980.25570.11540.056*0.729 (9)
H7B1.10810.10860.09610.056*0.729 (9)
H7C1.17570.17290.26950.056*0.729 (9)
C80.5615 (7)0.3397 (4)0.4303 (9)0.0338 (8)0.729 (9)
H8A0.61990.42000.43910.051*0.729 (9)
H8B0.50260.32210.53720.051*0.729 (9)
H8C0.47570.34150.33550.051*0.729 (9)
O90.6916 (7)0.0774 (3)0.4407 (8)0.0283 (9)0.729 (9)
O100.8716 (9)0.3756 (3)0.2614 (9)0.0357 (11)0.729 (9)
N1B0.9361 (9)0.1715 (6)0.2909 (12)0.0312 (7)0.271 (9)
N2B0.8561 (8)0.0531 (6)0.2825 (8)0.0303 (5)0.271 (9)
H2B0.934 (4)0.0095 (19)0.262 (6)0.036*0.271 (9)
C3B0.72872 (15)0.02781 (11)0.38972 (16)0.0267 (3)0.271 (9)
N4B0.6426 (7)0.1328 (5)0.4453 (7)0.0288 (5)0.271 (9)
H4B0.541 (4)0.117 (2)0.493 (6)0.035*0.271 (9)
N5B0.6597 (8)0.2434 (6)0.3465 (10)0.0320 (6)0.271 (9)
C6B0.82944 (17)0.26960 (11)0.30117 (17)0.0285 (3)0.271 (9)
C7B1.097 (2)0.1774 (17)0.195 (4)0.0371 (10)0.271 (9)
H7D1.13900.26290.19260.056*0.271 (9)
H7E1.07380.14890.07730.056*0.271 (9)
H7F1.18520.12440.24960.056*0.271 (9)
C8B0.552 (2)0.3440 (12)0.409 (3)0.0338 (8)0.271 (9)
H8D0.55620.41380.32940.051*0.271 (9)
H8E0.59550.37010.52200.051*0.271 (9)
H8F0.43140.31540.41730.051*0.271 (9)
O9B0.673 (2)0.0775 (9)0.415 (2)0.0283 (9)0.271 (9)
O10B0.883 (3)0.3769 (9)0.290 (3)0.0357 (11)0.271 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0271 (9)0.0244 (6)0.0427 (19)0.0003 (5)0.0102 (10)0.0096 (8)
N20.0279 (10)0.0202 (6)0.0435 (14)0.0017 (7)0.0118 (9)0.0052 (9)
C30.0255 (6)0.0238 (6)0.0308 (7)0.0011 (5)0.0032 (5)0.0005 (5)
N40.0227 (8)0.0232 (7)0.0407 (13)0.0003 (6)0.0070 (8)0.0048 (8)
N50.0324 (10)0.0184 (6)0.0457 (17)0.0005 (6)0.0134 (9)0.0011 (9)
C60.0308 (6)0.0236 (6)0.0311 (7)0.0015 (5)0.0045 (5)0.0021 (5)
C70.0296 (9)0.0318 (7)0.051 (3)0.0004 (6)0.0133 (13)0.0077 (9)
C80.0352 (9)0.0260 (8)0.041 (2)0.0060 (6)0.0074 (13)0.0008 (8)
O90.0250 (14)0.0216 (5)0.039 (2)0.0013 (5)0.0050 (13)0.0031 (6)
O100.0417 (11)0.0227 (5)0.043 (3)0.0039 (4)0.0113 (15)0.0037 (7)
N1B0.0271 (9)0.0244 (6)0.0427 (19)0.0003 (5)0.0102 (10)0.0096 (8)
N2B0.0279 (10)0.0202 (6)0.0435 (14)0.0017 (7)0.0118 (9)0.0052 (9)
C3B0.0255 (6)0.0238 (6)0.0308 (7)0.0011 (5)0.0032 (5)0.0005 (5)
N4B0.0227 (8)0.0232 (7)0.0407 (13)0.0003 (6)0.0070 (8)0.0048 (8)
N5B0.0324 (10)0.0184 (6)0.0457 (17)0.0005 (6)0.0134 (9)0.0011 (9)
C6B0.0308 (6)0.0236 (6)0.0311 (7)0.0015 (5)0.0045 (5)0.0021 (5)
C7B0.0296 (9)0.0318 (7)0.051 (3)0.0004 (6)0.0133 (13)0.0077 (9)
C8B0.0352 (9)0.0260 (8)0.041 (2)0.0060 (6)0.0074 (13)0.0008 (8)
O9B0.0250 (14)0.0216 (5)0.039 (2)0.0013 (5)0.0050 (13)0.0031 (6)
O10B0.0417 (11)0.0227 (5)0.043 (3)0.0039 (4)0.0113 (15)0.0037 (7)
Geometric parameters (Å, º) top
N1—N21.434 (3)C8—H8A0.9800
N1—C71.459 (3)C8—H8B0.9800
N2—C31.356 (2)C8—H8C0.9800
C3—N41.356 (2)N1B—N2B1.422 (7)
C3—O91.242 (3)N1B—C7B1.465 (7)
N4—N51.432 (2)N2B—H2B0.921 (16)
N5—C61.365 (2)N4B—N5B1.433 (6)
N5—C81.456 (3)N4B—H4B0.886 (16)
C6—N11.370 (3)N5B—C8B1.459 (7)
C6—O101.234 (3)C7B—H7D0.9800
N2—H20.880 (14)C7B—H7E0.9800
N4—H40.916 (14)C7B—H7F0.9800
C7—H7A0.9800C8B—H8D0.9800
C7—H7B0.9800C8B—H8E0.9800
C7—H7C0.9800C8B—H8F0.9800
C6—N1—N2116.6 (2)N5—N4—H4115.1 (12)
C6—N1—C7120.7 (3)N2B—N1B—C7B112.6 (9)
N2—N1—C7112.4 (3)N1B—N2B—H2B112.8 (18)
N1—N2—C3117.30 (18)N5B—N4B—H4B118.6 (19)
N2—C3—N4114.89 (14)N4B—N5B—C8B112.4 (8)
N2—C3—O9120.9 (3)N1B—C7B—H7D109.5
N4—C3—O9124.2 (3)N1B—C7B—H7E109.5
C3—N4—N5115.38 (17)H7D—C7B—H7E109.5
N4—N5—C6116.72 (19)N1B—C7B—H7F109.5
N4—N5—C8113.2 (3)H7D—C7B—H7F109.5
C6—N5—C8119.6 (3)H7E—C7B—H7F109.5
N5—C6—N1113.93 (16)N5B—C8B—H8D109.5
N5—C6—O10123.2 (3)N5B—C8B—H8E109.5
N1—C6—O10122.8 (3)H8D—C8B—H8E109.5
C3—N2—H2118.7 (12)N5B—C8B—H8F109.5
N1—N2—H2115.8 (12)H8D—C8B—H8F109.5
C3—N4—H4113.4 (11)H8E—C8B—H8F109.5
C6—N1—N2—C343.8 (3)N4—N5—C6—O10155.8 (4)
C7—N1—N2—C3170.7 (4)C8—N5—C6—O1013.4 (6)
N1—N2—C3—O9164.8 (4)N4—N5—C6—N121.6 (2)
N1—N2—C3—N416.1 (2)C8—N5—C6—N1164.0 (4)
O9—C3—N4—N5151.4 (4)N2—N1—C6—O10160.3 (4)
N2—C3—N4—N527.8 (2)C7—N1—C6—O1017.9 (7)
C3—N4—N5—C649.5 (3)N2—N1—C6—N522.3 (3)
C3—N4—N5—C8165.8 (3)C7—N1—C6—N5164.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10i0.88 (1)1.92 (2)2.791 (4)172 (2)
N4—H4···O9ii0.92 (1)1.90 (2)2.813 (6)177 (2)
N2—H2···O10Bi0.88 (1)1.94 (2)2.802 (11)166 (2)
N4—H4···O9Bii0.92 (1)1.89 (2)2.805 (16)174 (2)
N2B—H2B···O10i0.92 (2)1.96 (2)2.867 (8)170 (4)
N2B—H2B···O10Bi0.92 (2)1.92 (2)2.835 (13)172 (2)
N4B—H4B···O9ii0.89 (2)1.93 (2)2.805 (8)171 (5)
N4B—H4B···O9Bii0.89 (2)1.87 (2)2.750 (16)177 (4)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y, z+1.
 

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