organic compounds
The structure of the title compound, CH9N52+·2Cl−, has been determined. Strong N—HCl bonds are present, leading to a complex pattern of hydrogen-bonded rings.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302840X/rn6008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680302840X/rn6008Isup2.hkl |
CCDC reference: 232159
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+·2Cl− | F(000) = 336.000 |
Mr = 162.02 | Dx = 1.627 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 21 reflections |
a = 4.503 (2) Å | θ = 10–12° |
b = 21.234 (8) Å | µ = 0.89 mm−1 |
c = 6.936 (2) Å | T = 293 K |
β = 94.36 (3)° | Prism, colourless |
V = 661.3 (4) Å3 | 0.40 × 0.10 × 0.10 mm |
Z = 4 |
Data collection top
Siemens P3 4-circle diffractometer | Rint = 0.03 |
Graphite monochromator | θmax = 30.0°, θmin = 1.9° |
ω scans | h = −6→6 |
Absorption correction: ψ scan Platon (Spek, 1990) | k = −29→25 |
Tmin = 0.874, Tmax = 0.912 | l = 0→9 |
3211 measured reflections | 2 standard reflections every 0 reflections |
1840 independent reflections | intensity decay: 6.0% |
1404 reflections with I > 2σ(I) |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | H-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 reflections | Δρmax = 0.70 e Å−3 |
73 parameters | Δρmin = −0.39 e Å−3 |
0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.05069 (18) | 0.20793 (4) | 0.53939 (12) | 0.0302 | |
Cl2 | 0.81842 (19) | 0.04282 (4) | 1.28699 (12) | 0.0305 | |
N3 | 0.1977 (6) | 0.08878 (14) | 0.9372 (4) | 0.0309 | |
N4 | 0.4223 (7) | 0.17770 (14) | 1.1748 (4) | 0.0337 | |
N5 | 0.5227 (7) | 0.17040 (13) | 0.9888 (4) | 0.0304 | |
C6 | 0.4137 (7) | 0.12442 (15) | 0.8830 (4) | 0.0244 | |
N7 | 0.5385 (6) | 0.11292 (14) | 0.7148 (4) | 0.0271 | |
N8 | 0.3505 (6) | 0.08904 (13) | 0.5597 (4) | 0.0268 | |
H11 | 0.6121 (7) | 0.20611 (13) | 0.9485 (4) | 0.0500* | |
H12 | 0.1457 (6) | 0.09957 (14) | 1.0497 (4) | 0.0500* | |
H13 | 0.1565 (6) | 0.05325 (14) | 0.8817 (4) | 0.0500* | |
H14 | 0.6606 (6) | 0.14576 (14) | 0.6828 (4) | 0.0500* | |
H15 | 0.2294 (6) | 0.11352 (13) | 0.5075 (4) | 0.0500* | |
H16 | 0.2694 (6) | 0.04764 (13) | 0.5930 (4) | 0.0500* | |
H17 | 0.4535 (6) | 0.08205 (13) | 0.4625 (4) | 0.0500* | |
H9 | 0.2992 | 0.2096 | 1.1840 | 0.0500* | |
H10 | 0.5867 | 0.1893 | 1.2780 | 0.0500* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0294 (4) | 0.0271 (4) | 0.0346 (4) | −0.0008 (3) | 0.0058 (3) | 0.0010 (3) |
Cl2 | 0.0361 (4) | 0.0274 (4) | 0.0291 (4) | −0.0016 (3) | 0.0100 (3) | 0.0001 (3) |
N3 | 0.0339 (15) | 0.0343 (15) | 0.0254 (14) | −0.0125 (13) | 0.0084 (11) | −0.0023 (11) |
N4 | 0.0402 (16) | 0.0326 (15) | 0.0282 (14) | 0.0043 (13) | 0.0029 (12) | −0.0055 (12) |
N5 | 0.0352 (15) | 0.0260 (14) | 0.0299 (14) | −0.0062 (12) | 0.0022 (12) | 0.0006 (11) |
C6 | 0.0233 (15) | 0.0263 (15) | 0.0235 (14) | −0.0005 (12) | 0.0020 (11) | 0.0025 (11) |
N7 | 0.0230 (12) | 0.0334 (14) | 0.0255 (13) | −0.0076 (12) | 0.006 (1) | −0.0001 (11) |
N8 | 0.0300 (14) | 0.0291 (14) | 0.0217 (13) | 0.0003 (11) | 0.0047 (11) | 0.001 (1) |
Geometric parameters (Å, º) top
N3—H13 | 0.861 | N5—C6 | 1.299 (4) |
N3—H12 | 0.863 | C6—N7 | 1.351 (4) |
N3—C6 | 1.313 (4) | N7—H14 | 0.925 |
N4—H10 | 1.011 | N7—N8 | 1.412 (4) |
N4—H9 | 0.868 | N8—H17 | 0.860 |
N4—N5 | 1.414 (4) | N8—H16 | 0.986 |
N5—H11 | 0.912 | N8—H15 | 0.818 |
H13—N3—H12 | 124.962 | N5—C6—N3 | 122.2 (3) |
H13—N3—C6 | 121.248 | H14—N7—N8 | 114.932 |
H12—N3—C6 | 111.485 | H14—N7—C6 | 111.179 |
H10—N4—H9 | 100.005 | N8—N7—C6 | 117.1 (3) |
H10—N4—N5 | 113.647 | H17—N8—H16 | 105.161 |
H9—N4—N5 | 113.143 | H17—N8—H15 | 98.302 |
H11—N5—C6 | 127.689 | H16—N8—H15 | 115.081 |
H11—N5—N4 | 111.836 | H17—N8—N7 | 109.374 |
C6—N5—N4 | 118.1 (3) | H16—N8—N7 | 110.705 |
N7—C6—N5 | 117.3 (3) | H15—N8—N7 | 116.765 |
N7—C6—N3 | 120.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H9···Cl1i | 0.88 | 2.51 | 3.318 (3) | 152 |
N4—H10···Cl1ii | 1.02 | 2.38 | 3.395 (3) | 174 |
N5—H11···Cl1iii | 0.91 | 2.43 | 3.223 (3) | 146 |
N3—H12···Cl2iv | 0.86 | 2.59 | 3.223 (3) | 131 |
N3—H12···N4 | 0.86 | 2.21 | 2.655 (4) | 112 |
N3—H13···Cl2v | 0.86 | 2.36 | 3.196 (3) | 164 |
N7—H14···Cl1vi | 0.93 | 2.15 | 3.052 (3) | 165 |
N8—H15···Cl1 | 0.82 | 2.39 | 3.101 (3) | 146 |
N8—H15···Cl2vii | 0.82 | 2.75 | 3.097 (3) | 107 |
N8—H16···Cl2v | 0.99 | 2.14 | 3.110 (3) | 167 |
N8—H17···Cl2viii | 0.86 | 2.28 | 3.096 (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) x−1, y, z; (v) −x+1, −y, −z+2; (vi) x+1, y, z; (vii) x−1, y, z−1; (viii) x, y, z−1. |