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In the title compound, C4H8N22+·2NO3, the piperazinium dication has a centre of symmetry. The ions are linked by N—H...O hydrogen bonds into a chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053724/cf2077sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053724/cf2077Isup2.hkl
Contains datablock I

CCDC reference: 633641

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.090
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.768 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.17 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff et al., 1996); software used to prepare material for publication: SHELXL97.

Piperazinium dinitrate top
Crystal data top
C4H12N22+·2NO3F(000) = 448
Mr = 212.18Dx = 1.521 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 220 reflections
a = 14.6895 (3) Åθ = 3.2–28.0°
b = 5.9301 (1) ŵ = 0.14 mm1
c = 12.4018 (4) ÅT = 273 K
β = 120.956 (1)°Prism, colourless
V = 926.44 (4) Å30.30 × 0.20 × 0.06 mm
Z = 4
Data collection top
Siemens SMART 1K CCD area-detector
diffractometer
1104 independent reflections
Radiation source: fine-focus sealed tube535 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
φ and ω scansθmax = 28.0°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1917
Tmin = 0.88, Tmax = 1.00k = 77
3535 measured reflectionsl = 1615
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 0.77 w = 1/[σ2(Fo2) + (0.0417P)2]
where P = (Fo2 + 2Fc2)/3
1104 reflections(Δ/σ)max < 0.001
64 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.17 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*/Ueq
O10.54413 (10)0.5314 (2)0.14290 (12)0.0722 (4)
O20.52868 (9)0.8925 (2)0.12489 (12)0.0618 (4)
O30.38913 (9)0.6852 (2)0.04531 (13)0.0634 (4)
N10.35353 (10)0.2016 (2)0.02326 (13)0.0481 (4)
H1A0.37970.34110.02870.058*
H1D0.40410.10180.03530.058*
N20.48815 (12)0.7018 (3)0.10557 (13)0.0466 (4)
C10.32719 (13)0.1720 (3)0.12294 (16)0.0522 (5)
H1B0.38990.19980.20450.063*
H1C0.30460.01790.12180.063*
C20.25956 (12)0.1689 (3)0.10341 (15)0.0492 (5)
H2A0.23480.01460.11240.059*
H2B0.27860.19630.16650.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0746 (9)0.0526 (9)0.0794 (9)0.0217 (7)0.0325 (7)0.0134 (8)
O20.0505 (7)0.0463 (8)0.0881 (10)0.0089 (6)0.0352 (7)0.0137 (7)
O30.0455 (8)0.0508 (8)0.0927 (10)0.0077 (6)0.0347 (7)0.0103 (7)
N10.0342 (7)0.0401 (8)0.0683 (10)0.0012 (6)0.0252 (7)0.0064 (7)
N20.0520 (9)0.0430 (9)0.0506 (9)0.0014 (8)0.0306 (8)0.0031 (8)
C10.0447 (10)0.0512 (12)0.0467 (10)0.0053 (9)0.0135 (8)0.0001 (9)
C20.0459 (10)0.0501 (12)0.0504 (10)0.0018 (8)0.0241 (8)0.0064 (9)
Geometric parameters (Å, º) top
O1—N21.2329 (17)C1—C2i1.502 (2)
O2—N21.2425 (17)C1—H1B0.970
O3—N21.2513 (17)C1—H1C0.970
N1—C21.476 (2)C2—C1i1.502 (2)
N1—C11.483 (2)C2—H2A0.970
N1—H1A0.900C2—H2B0.970
N1—H1D0.900
C2—N1—C1111.67 (13)C2i—C1—H1B109.5
C2—N1—H1A109.3N1—C1—H1C109.5
C1—N1—H1A109.3C2i—C1—H1C109.5
C2—N1—H1D109.3H1B—C1—H1C108.1
C1—N1—H1D109.3N1—C2—C1i109.90 (13)
H1A—N1—H1D107.9N1—C2—H2A109.7
O1—N2—O2120.84 (15)C1i—C2—H2A109.7
O1—N2—O3120.39 (16)N1—C2—H2B109.7
O2—N2—O3118.76 (16)C1i—C2—H2B109.7
N1—C1—C2i110.78 (13)H2A—C2—H2B108.2
N1—C1—H1B109.5
Symmetry code: (i) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.902.052.9025 (17)158
N1—H1D···O2ii0.902.012.8694 (17)160
Symmetry code: (ii) x, y1, z.
 

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