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The structure of the title compound, CH9N52+·2Cl, has been determined. Strong N—H...Cl bonds are present, leading to a complex pattern of hydrogen-bonded rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302840X/rn6008sup1.cif
Contains datablocks CRYSTALS, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302840X/rn6008Isup2.hkl
Contains datablock I

CCDC reference: 232159

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](N-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.090
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT353_ALERT_3_C Long N-H Bond (0.87A) N4 - H10 = 1.02 Ang. PLAT701_ALERT_1_C Bond Calc 1.408(4), Rep 1.414(4), Dev.. 1.50 Sigma N4 -N5 1.555 1.555
Author Response: The hydrogen atom was clearly found by a difference Fourier synthesis at the specified distance from N4. Placing it geometrically gave a significant worse agreement factor. Moreover, from the presence of two Cl ions it is clear that the di-aminoguanidinium ion should be protonated to give a formal charge of 2+. Assigning the positive density in the difference Fourier map to a proton was the only possibility to get an overall neutral charge, although it may be a bit displaced.
PLAT721_ALERT_1_C Bond    Calc     0.88065, Rep     0.86800, Dev.        0.01 Ang.
              N4   -H9      1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl

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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: P3 (Siemens, 1993); cell refinement: P3; data reduction: XDISK in P3; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: Mercury (CCDC, 2002) and PLATON (Spek, 2003); software used to prepare material for publication: CRYSTALS.

(I) top
Crystal data top
CH9N52+·2ClF(000) = 336.000
Mr = 162.02Dx = 1.627 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 21 reflections
a = 4.503 (2) Åθ = 10–12°
b = 21.234 (8) ŵ = 0.89 mm1
c = 6.936 (2) ÅT = 293 K
β = 94.36 (3)°Prism, colourless
V = 661.3 (4) Å30.40 × 0.10 × 0.10 mm
Z = 4
Data collection top
Siemens P3 4-circle
diffractometer
Rint = 0.03
Graphite monochromatorθmax = 30.0°, θmin = 1.9°
ω scansh = 66
Absorption correction: ψ scan
Platon (Spek, 1990)
k = 2925
Tmin = 0.874, Tmax = 0.912l = 09
3211 measured reflections2 standard reflections every 0 reflections
1840 independent reflections intensity decay: 6.0%
1404 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.090 %TMethod, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982). ηfilβreak [weight] = $1.0/[A_0T_0(x) + A_1T_1(x) ··· + A_{n-1}]T_{n-1}(x)]$
where A$_i$ are the Chebychev coefficients listed below and $x$ = F$_{µathrm{ }}$/F$_{µathrm{max}}.$ηfilβreak Method = Robust Weighting (Prince, 1982).ηfilβreak W = [weight] * [1-(Δelta F/6σigma F)$2$]$2$.ηfilβreak A$_{0-2}$ are 10.8, 13.7, and 4.14, respectively.
S = 1.00(Δ/σ)max = 0.001
1404 reflectionsΔρmax = 0.70 e Å3
73 parametersΔρmin = 0.39 e Å3
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.05069 (18)0.20793 (4)0.53939 (12)0.0302
Cl20.81842 (19)0.04282 (4)1.28699 (12)0.0305
N30.1977 (6)0.08878 (14)0.9372 (4)0.0309
N40.4223 (7)0.17770 (14)1.1748 (4)0.0337
N50.5227 (7)0.17040 (13)0.9888 (4)0.0304
C60.4137 (7)0.12442 (15)0.8830 (4)0.0244
N70.5385 (6)0.11292 (14)0.7148 (4)0.0271
N80.3505 (6)0.08904 (13)0.5597 (4)0.0268
H110.6121 (7)0.20611 (13)0.9485 (4)0.0500*
H120.1457 (6)0.09957 (14)1.0497 (4)0.0500*
H130.1565 (6)0.05325 (14)0.8817 (4)0.0500*
H140.6606 (6)0.14576 (14)0.6828 (4)0.0500*
H150.2294 (6)0.11352 (13)0.5075 (4)0.0500*
H160.2694 (6)0.04764 (13)0.5930 (4)0.0500*
H170.4535 (6)0.08205 (13)0.4625 (4)0.0500*
H90.29920.20961.18400.0500*
H100.58670.18931.27800.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0294 (4)0.0271 (4)0.0346 (4)0.0008 (3)0.0058 (3)0.0010 (3)
Cl20.0361 (4)0.0274 (4)0.0291 (4)0.0016 (3)0.0100 (3)0.0001 (3)
N30.0339 (15)0.0343 (15)0.0254 (14)0.0125 (13)0.0084 (11)0.0023 (11)
N40.0402 (16)0.0326 (15)0.0282 (14)0.0043 (13)0.0029 (12)0.0055 (12)
N50.0352 (15)0.0260 (14)0.0299 (14)0.0062 (12)0.0022 (12)0.0006 (11)
C60.0233 (15)0.0263 (15)0.0235 (14)0.0005 (12)0.0020 (11)0.0025 (11)
N70.0230 (12)0.0334 (14)0.0255 (13)0.0076 (12)0.006 (1)0.0001 (11)
N80.0300 (14)0.0291 (14)0.0217 (13)0.0003 (11)0.0047 (11)0.001 (1)
Geometric parameters (Å, º) top
N3—H130.861N5—C61.299 (4)
N3—H120.863C6—N71.351 (4)
N3—C61.313 (4)N7—H140.925
N4—H101.011N7—N81.412 (4)
N4—H90.868N8—H170.860
N4—N51.414 (4)N8—H160.986
N5—H110.912N8—H150.818
H13—N3—H12124.962N5—C6—N3122.2 (3)
H13—N3—C6121.248H14—N7—N8114.932
H12—N3—C6111.485H14—N7—C6111.179
H10—N4—H9100.005N8—N7—C6117.1 (3)
H10—N4—N5113.647H17—N8—H16105.161
H9—N4—N5113.143H17—N8—H1598.302
H11—N5—C6127.689H16—N8—H15115.081
H11—N5—N4111.836H17—N8—N7109.374
C6—N5—N4118.1 (3)H16—N8—N7110.705
N7—C6—N5117.3 (3)H15—N8—N7116.765
N7—C6—N3120.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H9···Cl1i0.882.513.318 (3)152
N4—H10···Cl1ii1.022.383.395 (3)174
N5—H11···Cl1iii0.912.433.223 (3)146
N3—H12···Cl2iv0.862.593.223 (3)131
N3—H12···N40.862.212.655 (4)112
N3—H13···Cl2v0.862.363.196 (3)164
N7—H14···Cl1vi0.932.153.052 (3)165
N8—H15···Cl10.822.393.101 (3)146
N8—H15···Cl2vii0.822.753.097 (3)107
N8—H16···Cl2v0.992.143.110 (3)167
N8—H17···Cl2viii0.862.283.096 (3)160
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x1, y, z; (v) x+1, y, z+2; (vi) x+1, y, z; (vii) x1, y, z1; (viii) x, y, z1.
 

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