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The title compound, C2H8N+·NO3, is composed of discrete cations and anions which are connected by classical N—H...O hydrogen bonds. Geometric parameters are in the usual ranges.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054839/at2464sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054839/at2464Isup2.hkl
Contains datablock I

CCDC reference: 674082

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](O-N) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.087
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.23 Sigma
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.29 From the CIF: _reflns_number_total 557 Count of symmetry unique reflns 558 Completeness (_total/calc) 99.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Poly(pyrazol-1-yl)borates ("scorpionates") are among the most important ligands in transition metal chemistry and were invented by Trofimenko more than 30 years ago (Trofimenko, 1993). Recently, we have extended our studies to ditopic scorpionates with meta- and para-phenylene backbones. Our studies have shown that the synthesis of scorpionates can conveniently be achieved by reaction of bis(dimethylamino)arylboranes and pyrazole or pyrazole derivatives in the presence of bases (Bieller et al., 2005; Zhang et al., 2004). In attempting to synthesize a zinc complex with the [C6F5Bpz3] ligand (pz = pyrazolyl) from C6F5B(NMe2)2 (Me = CH3) and [Znpz4(NO3)2] (Vitze et al., 2006) we obtained the title compound, H2NMe2NO3, as a by-product. Single crystals of H2NMe2NO3 were obtained from a mixture of tetrahydrofuran/hexane at ambient temperature.

The title compound is composed of discrete cations and anions (Fig. 1) which are connected by classical N—H···O hydrogen bonds. Two of the nitrate O atoms accept two hydrogen bonds, whereas the third one just accepts one (Fig. 2). Geometric parameters are in the usual ranges.

Related literature top

For related literature, see: Bieller et al. (2005); Flack (1983); Trofimenko (1993); Vitze et al. (2006); Zhang et al. (2004).

Experimental top

A mixture of C6F5B(NMe2)2 (0.266 g) and [Znpz4(NO3)2] (Vitze et al., 2006) in 6 ml tetrahydrofuran and 6 ml NEt3 was refluxed for 1 h. After removal of the solvent in vacuo the residue was extracted with tetrahydrofuran. Layering with hexane led to the deposition of crystals of H2NMe2NO3 at ambient temperature.

Refinement top

All H atoms could be located by difference Fourier synthesis. They were refined with fixed individual displacement parameters [Uiso(H) = 1.2 Ueq(N) or Uiso(H) = 1.5 Ueq(C)] using a riding model with N—H = 0.92 Å or C—H = 0.98 Å, respectively. In the absence of anomalous scatterers, the Flack (1983) parameter is meaningless and therefore, Friedel pairs had been merged prior to refinement.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound with view onto the ab plane. Hydrogen bonds are drawn as dashed lines.
Dimethylammonium nitrate top
Crystal data top
C2H8N+·NO3F(000) = 232
Mr = 108.10Dx = 1.291 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3599 reflections
a = 9.9552 (18) Åθ = 4.1–25.4°
b = 9.7684 (12) ŵ = 0.12 mm1
c = 5.7191 (7) ÅT = 173 K
V = 556.16 (14) Å3Plate, colourless
Z = 40.37 × 0.17 × 0.08 mm
Data collection top
STOE IPDS II two-circle-
diffractometer
492 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.081
Graphite monochromatorθmax = 25.3°, θmin = 4.1°
ω scansh = 1110
4065 measured reflectionsk = 1110
557 independent reflectionsl = 66
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0532P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
557 reflectionsΔρmax = 0.14 e Å3
65 parametersΔρmin = 0.12 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.042 (13)
Crystal data top
C2H8N+·NO3V = 556.16 (14) Å3
Mr = 108.10Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 9.9552 (18) ŵ = 0.12 mm1
b = 9.7684 (12) ÅT = 173 K
c = 5.7191 (7) Å0.37 × 0.17 × 0.08 mm
Data collection top
STOE IPDS II two-circle-
diffractometer
492 reflections with I > 2σ(I)
4065 measured reflectionsRint = 0.081
557 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0361 restraint
wR(F2) = 0.087H-atom parameters constrained
S = 1.07Δρmax = 0.14 e Å3
557 reflectionsΔρmin = 0.12 e Å3
65 parameters
Special details top

Experimental. ;

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
N10.4727 (2)0.2067 (2)0.4304 (4)0.0357 (5)
O10.52001 (19)0.1106 (2)0.3073 (4)0.0427 (6)
O20.5451 (2)0.2631 (2)0.5812 (4)0.0460 (6)
O30.3538 (2)0.2435 (2)0.3993 (5)0.0614 (8)
C10.3170 (4)0.5648 (3)0.5141 (6)0.0487 (8)
H1A0.27220.58970.36760.073*
H1B0.39910.51330.47930.073*
H1C0.34010.64810.60070.073*
N20.2255 (2)0.4789 (2)0.6577 (4)0.0348 (6)
H2A0.20210.40220.57360.042*
H2B0.14820.52740.68790.042*
C20.2866 (3)0.4355 (3)0.8836 (5)0.0452 (7)
H2C0.22210.37940.97080.068*
H2D0.30990.51660.97580.068*
H2E0.36790.38190.85270.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0295 (11)0.0322 (12)0.0452 (13)0.0013 (9)0.0008 (12)0.0014 (11)
O10.0356 (11)0.0484 (13)0.0440 (10)0.0081 (9)0.0035 (9)0.0096 (10)
O20.0388 (11)0.0438 (12)0.0556 (14)0.0041 (9)0.0129 (10)0.0129 (10)
O30.0350 (12)0.0566 (15)0.0927 (19)0.0132 (9)0.0180 (13)0.0332 (14)
C10.0600 (19)0.0417 (16)0.0444 (17)0.0017 (15)0.0152 (15)0.0015 (14)
N20.0331 (11)0.0348 (12)0.0364 (12)0.0030 (9)0.0031 (10)0.0093 (10)
C20.0510 (17)0.0467 (17)0.0379 (16)0.0021 (14)0.0003 (13)0.0014 (13)
Geometric parameters (Å, º) top
N1—O31.249 (3)N2—C21.489 (4)
N1—O21.252 (3)N2—H2A0.9200
N1—O11.264 (3)N2—H2B0.9200
C1—N21.487 (4)C2—H2C0.9800
C1—H1A0.9800C2—H2D0.9800
C1—H1B0.9800C2—H2E0.9800
C1—H1C0.9800
O3—N1—O2121.1 (3)C2—N2—H2A109.0
O3—N1—O1119.2 (2)C1—N2—H2B109.0
O2—N1—O1119.7 (2)C2—N2—H2B109.0
N2—C1—H1A109.5H2A—N2—H2B107.8
N2—C1—H1B109.5N2—C2—H2C109.5
H1A—C1—H1B109.5N2—C2—H2D109.5
N2—C1—H1C109.5H2C—C2—H2D109.5
H1A—C1—H1C109.5N2—C2—H2E109.5
H1B—C1—H1C109.5H2C—C2—H2E109.5
C1—N2—C2112.9 (2)H2D—C2—H2E109.5
C1—N2—H2A109.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.922.383.018 (3)126
N2—H2B···O1i0.921.982.892 (3)169
N2—H2B···O3i0.922.433.035 (3)123
N2—H2A···O1ii0.922.372.994 (3)125
N2—H2A···O2ii0.922.253.000 (3)139
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC2H8N+·NO3
Mr108.10
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)173
a, b, c (Å)9.9552 (18), 9.7684 (12), 5.7191 (7)
V3)556.16 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.37 × 0.17 × 0.08
Data collection
DiffractometerSTOE IPDS II two-circle-
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4065, 557, 492
Rint0.081
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.087, 1.07
No. of reflections557
No. of parameters65
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.12

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.922.383.018 (3)126.0
N2—H2B···O1i0.921.982.892 (3)169.2
N2—H2B···O3i0.922.433.035 (3)123.2
N2—H2A···O1ii0.922.372.994 (3)124.9
N2—H2A···O2ii0.922.253.000 (3)138.6
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z.
 

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