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The title compound, a promising new energetic material, 3,3-bis­(di­fluoro­amino­methyl)­oxetane, (F2NCH2)2C(CH2)2O or C5H8F4N2O, contains two difluoro­amine (NF2) substituents, rather uncommon energetic groups, which tend to be disordered in crystal structures. The mol­ecule occupies a special position on a twofold axis, and its two equivalent difluoro­amine groups show no signs of disorder.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027016/ya6177sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027016/ya6177Isup2.hkl
Contains datablock I

CCDC reference: 227923

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.036
  • wR factor = 0.102
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C4 = 5.30 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 2 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: SMART (Bruker,2001); cell refinement: SAINT (Bruker,2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3,3-bis(difluoroaminomethyl)oxetane top
Crystal data top
C5H8F4N2OF(000) = 384
Mr = 188.13Dx = 1.728 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2766 reflections
a = 10.3304 (13) Åθ = 2.9–28.5°
b = 10.6065 (13) ŵ = 0.19 mm1
c = 6.8638 (8) ÅT = 93 K
β = 105.931 (2)°Rounded chunk, colorless
V = 723.18 (15) Å30.70 × 0.65 × 0.60 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer
877 independent reflections
Radiation source: fine-focus sealed tube840 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 28.2°, θmin = 2.8°
Absorption correction: integration
(Wuensch & Prewitt, 1965)
h = 1213
Tmin = 0.858, Tmax = 0.919k = 1414
2995 measured reflectionsl = 88
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.102Only H-atom coordinates refined
S = 1.00 w = 1/[σ2(Fo2) + (0.0627P)2 + 0.609P]
where P = (Fo2 + 2Fc2)/3
877 reflections(Δ/σ)max = 0.002
72 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.26 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 > 2σ(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
F5A0.12220 (7)0.42556 (7)0.04368 (11)0.0225 (3)
F5B0.23894 (7)0.30290 (7)0.19704 (11)0.0214 (3)
O10.00000.01437 (11)0.25000.0202 (3)
C20.10373 (11)0.08116 (10)0.18578 (17)0.0160 (3)
H2A0.1480 (16)0.0769 (14)0.042 (3)0.019*
H2B0.1717 (17)0.0754 (13)0.262 (3)0.019*
C30.00000.18930 (13)0.25000.0125 (3)
N50.11361 (9)0.36818 (9)0.13797 (14)0.0161 (3)
C40.01238 (11)0.26786 (10)0.06953 (16)0.0138 (3)
H4A0.0654 (16)0.3128 (14)0.009 (2)0.017*
H4B0.0346 (15)0.2159 (14)0.026 (2)0.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F5A0.0229 (4)0.0209 (4)0.0261 (4)0.0036 (3)0.0110 (3)0.0075 (3)
F5B0.0110 (4)0.0238 (4)0.0284 (4)0.0008 (2)0.0035 (3)0.0017 (3)
O10.0200 (6)0.0106 (5)0.0306 (6)0.0000.0076 (5)0.000
C20.0148 (5)0.0116 (5)0.0222 (6)0.0023 (4)0.0060 (4)0.0001 (4)
C30.0105 (6)0.0106 (7)0.0172 (7)0.0000.0052 (5)0.000
N50.0141 (5)0.0155 (5)0.0206 (5)0.0007 (3)0.0076 (4)0.0025 (3)
C40.0122 (5)0.0131 (5)0.0165 (5)0.0014 (4)0.0048 (4)0.0001 (4)
Geometric parameters (Å, º) top
F5A—N51.4120 (11)C2—H2B0.987 (17)
F5B—N51.4255 (11)C3—C41.5271 (13)
O1—C21.4526 (13)N5—C41.4754 (14)
C2—C31.5488 (14)C4—H4A0.929 (16)
C2—H2A0.968 (16)C4—H4B0.931 (16)
C2i—O1—C291.54 (11)C2—C3—C2i84.45 (11)
O1—C2—C392.01 (8)F5A—N5—F5B100.85 (7)
O1—C2—H2A112.3 (9)F5A—N5—C4103.92 (8)
C3—C2—H2A114.9 (9)F5B—N5—C4104.44 (8)
O1—C2—H2B111.6 (9)N5—C4—C3110.19 (8)
C3—C2—H2B115.6 (9)N5—C4—H4A102.9 (9)
H2A—C2—H2B109.5 (14)C3—C4—H4A113.0 (9)
C4i—C3—C4113.86 (12)N5—C4—H4B111.2 (9)
C4i—C3—C2115.43 (6)C3—C4—H4B109.8 (9)
C4—C3—C2112.25 (6)H4A—C4—H4B109.7 (14)
C2i—O1—C2—C30.0F5B—N5—C4—C370.06 (10)
O1—C2—C3—C4i112.03 (8)C4i—C3—C4—N547.35 (6)
O1—C2—C3—C4115.24 (8)C2—C3—C4—N5179.15 (8)
O1—C2—C3—C2i0.0C2i—C3—C4—N584.63 (11)
F5A—N5—C4—C3175.36 (7)
Symmetry code: (i) x, y, z+1/2.
 

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