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The crystal structure of the title compound, C5H9N32+·2Cl, is stabilized by N—H...Cl hydrogen bonds, forming a three-dimensional network. Each chloride anion forms three hydrogen bonds with N atoms, and the hydrazine unit forms R21(5) motifs with one of the Cl anions. The aromatic ring is almost coplanar with both the N atoms of the hydrazine substituent and with one of the Cl anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020502/sj2084sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020502/sj2084Isup2.hkl
Contains datablock I

CCDC reference: 613821

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.068
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Pyridiniohydrazinium chloride top
Crystal data top
C5H9N32+·2ClF(000) = 376
Mr = 182.05Dx = 1.516 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8773 reflections
a = 7.3787 (11) Åθ = 2.4–27.9°
b = 8.5682 (9) ŵ = 0.74 mm1
c = 12.637 (2) ÅT = 296 K
β = 93.179 (12)°Plate, brown
V = 797.70 (19) Å30.58 × 0.47 × 0.31 mm
Z = 4
Data collection top
Stoe IPDS II
diffractometer
1564 independent reflections
Radiation source: fine-focus sealed tube1388 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.9°
rotation ω scansh = 89
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1010
Tmin = 0.684, Tmax = 0.826l = 1515
4066 measured reflections
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0349P)2 + 0.2627P]
where P = (Fo2 + 2Fc2)/3
1564 reflections(Δ/σ)max < 0.001
95 parametersΔρmax = 0.22 e Å3
0 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*/Ueq
C10.60144 (19)0.52183 (17)0.66215 (11)0.0286 (3)
C20.5538 (2)0.67694 (17)0.67555 (12)0.0302 (3)
H20.49030.70730.73370.036*
C30.6015 (2)0.78465 (19)0.60203 (12)0.0351 (3)
H30.56780.88850.60950.042*
C40.6998 (2)0.7402 (2)0.51635 (13)0.0420 (4)
H40.73270.81320.46650.050*
C50.7465 (2)0.5885 (2)0.50712 (13)0.0419 (4)
H50.81420.55670.45100.050*
N10.69561 (17)0.48306 (16)0.57857 (10)0.0348 (3)
H10.72480.38690.57020.042*
N20.5649 (2)0.40280 (17)0.72846 (12)0.0393 (3)
N30.45364 (19)0.43148 (16)0.81355 (11)0.0380 (3)
H3A0.44120.34400.85040.057*
H3B0.34510.46400.78840.057*
H3C0.50440.50460.85550.057*
Cl20.08968 (5)0.57196 (5)0.73078 (3)0.03771 (13)
Cl10.81741 (6)0.15165 (5)0.54009 (3)0.04181 (14)
H2A0.566 (3)0.310 (3)0.7086 (18)0.059 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0270 (7)0.0267 (7)0.0315 (7)0.0003 (6)0.0041 (6)0.0023 (6)
C20.0325 (8)0.0264 (7)0.0322 (7)0.0002 (6)0.0053 (6)0.0029 (6)
C30.0385 (8)0.0273 (8)0.0394 (8)0.0019 (7)0.0011 (6)0.0007 (6)
C40.0442 (9)0.0467 (10)0.0355 (8)0.0084 (8)0.0059 (7)0.0053 (7)
C50.0361 (9)0.0576 (11)0.0327 (8)0.0007 (8)0.0072 (7)0.0086 (7)
N10.0341 (7)0.0320 (7)0.0380 (7)0.0059 (6)0.0003 (5)0.0099 (6)
N20.0499 (9)0.0233 (7)0.0449 (8)0.0011 (6)0.0055 (6)0.0012 (6)
N30.0398 (7)0.0367 (7)0.0374 (7)0.0058 (6)0.0000 (6)0.0095 (6)
Cl20.0408 (2)0.0320 (2)0.0407 (2)0.00518 (16)0.00586 (16)0.00246 (15)
Cl10.0522 (3)0.0321 (2)0.0412 (2)0.01060 (18)0.00353 (17)0.00033 (16)
Geometric parameters (Å, º) top
C1—N11.338 (2)C5—N11.345 (2)
C1—N21.356 (2)C5—H50.9300
C1—C21.388 (2)N1—H10.8600
C2—C31.369 (2)N2—N31.410 (2)
C2—H20.9300N2—H2A0.83 (3)
C3—C41.389 (2)N3—H3A0.8900
C3—H30.9300N3—H3B0.8900
C4—C51.352 (3)N3—H3C0.8900
C4—H40.9300
N1—C1—N2115.51 (14)C4—C5—H5119.8
N1—C1—C2118.71 (14)C1—N1—C5122.67 (14)
N2—C1—C2125.76 (14)C1—N1—H1118.7
C3—C2—C1119.10 (14)C5—N1—H1118.7
C3—C2—H2120.4C1—N2—N3118.95 (14)
C1—C2—H2120.4C1—N2—H2A121.6 (16)
C2—C3—C4120.59 (15)N3—N2—H2A114.4 (16)
C2—C3—H3119.7N2—N3—H3A109.5
C4—C3—H3119.7N2—N3—H3B109.5
C5—C4—C3118.52 (16)H3A—N3—H3B109.5
C5—C4—H4120.7N2—N3—H3C109.5
C3—C4—H4120.7H3A—N3—H3C109.5
N1—C5—C4120.38 (15)H3B—N3—H3C109.5
N1—C5—H5119.8
N1—C1—C2—C31.2 (2)N2—C1—N1—C5178.24 (15)
N2—C1—C2—C3179.48 (15)C2—C1—N1—C50.2 (2)
C1—C2—C3—C41.4 (2)C4—C5—N1—C11.4 (2)
C2—C3—C4—C50.2 (3)N1—C1—N2—N3174.86 (13)
C3—C4—C5—N11.2 (3)C2—C1—N2—N36.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.862.173.0259 (14)175
N3—H3A···Cl2i0.892.553.1441 (15)125
N3—H3A···Cl1ii0.892.613.1674 (15)121
N3—H3B···Cl20.892.193.0730 (16)173
N3—H3C···Cl1iii0.892.213.0800 (15)167
N2—H2A···Cl2i0.83 (3)2.49 (3)3.1092 (15)132.6 (19)
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x1/2, y+1/2, z+1/2; (iii) x+3/2, y+1/2, z+3/2.
 

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