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In the title compound, C10HI2N2+·2CI, the naphthalene-1,5-diammonium ion lies on an inversion center; the asymmetric unit contains half of the cation and one Cl anion. The structure can be described as consisting of alternating layers of C10HI2N2+ and CI ions perpendicular to the a axis. The structure contains N—H...Cl hydrogen bonds, which build up a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043868/dn2077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043868/dn2077Isup2.hkl
Contains datablock I

CCDC reference: 627493

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.036
  • wR factor = 0.083
  • Data-to-parameter ratio = 22.7

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Computing details top

Data collection: Collect (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

(I) top
Crystal data top
C10H12N22+·2ClF(000) = 240
Mr = 231.12Dx = 1.454 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4491 reflections
a = 8.5766 (4) Åθ = 1.0–30.0°
b = 5.1650 (4) ŵ = 0.58 mm1
c = 12.2001 (7) ÅT = 173 K
β = 102.394 (1)°Needle, white
V = 527.85 (6) Å30.45 × 0.05 × 0.03 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
1265 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Detector resolution: 9 pixels mm-1θmax = 29.9°, θmin = 2.4°
φ scansh = 1211
4124 measured reflectionsk = 77
1523 independent reflectionsl = 1612
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0161P)2 + 0.2248P]
where P = (Fo2 + 2Fc2)/3
1523 reflections(Δ/σ)max < 0.001
67 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.27 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.44779 (5)0.21431 (7)0.35441 (3)0.02071 (13)
N10.34394 (15)0.2116 (2)0.08241 (11)0.0184 (3)
C10.08397 (17)0.0054 (3)0.00288 (13)0.0148 (3)
C20.17249 (17)0.1932 (3)0.07625 (13)0.0156 (3)
C30.10277 (19)0.3564 (3)0.13922 (13)0.0189 (3)
C40.06309 (19)0.3425 (3)0.13258 (13)0.0197 (3)
C50.15455 (19)0.1658 (3)0.06337 (13)0.0185 (3)
H10.26390.15810.05980.022*
H20.11080.45410.17550.024*
H30.16440.47650.18640.023*
H40.36150.23720.01390.035 (6)*
H50.3910.06530.11050.035 (5)*
H60.38380.34350.12650.045 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0229 (2)0.0219 (2)0.0170 (2)0.00300 (14)0.00343 (15)0.00044 (14)
N10.0157 (6)0.0213 (7)0.0174 (7)0.0035 (5)0.0021 (5)0.0014 (5)
C10.0154 (7)0.0150 (7)0.0140 (7)0.0002 (5)0.0030 (6)0.0026 (5)
C20.0138 (7)0.0175 (7)0.0150 (7)0.0015 (5)0.0019 (6)0.0025 (6)
C30.0214 (8)0.0176 (7)0.0163 (8)0.0030 (6)0.0012 (6)0.0013 (6)
C40.0221 (8)0.0186 (8)0.0192 (8)0.0025 (6)0.0059 (6)0.0018 (6)
C50.0158 (7)0.0205 (8)0.0194 (8)0.0002 (6)0.0041 (6)0.0008 (6)
Geometric parameters (Å, º) top
N1—C21.4593 (19)C3—C41.409 (2)
N1—H40.89C3—H30.93
N1—H50.89C4—C51.370 (2)
N1—H60.89C4—H20.93
C1—C1i1.428 (3)C5—C1i1.418 (2)
C1—C21.424 (2)C5—H10.93
C3—C21.362 (2)
C2—N1—H4109.5C1—C2—N1118.18 (13)
C2—N1—H5109.5C2—C3—C4119.74 (14)
H4—N1—H5109.5C2—C3—H3120.1
C2—N1—H6109.5C4—C3—H3120.1
H4—N1—H6109.5C5—C4—C3120.44 (15)
H5—N1—H6109.5C5—C4—H2119.8
C5i—C1—C2123.22 (14)C3—C4—H2119.8
C5i—C1—C1i119.81 (17)C4—C5—C1i120.58 (14)
C2—C1—C1i116.97 (17)C4—C5—H1119.7
C3—C2—C1122.47 (14)C1i—C5—H1119.7
C3—C2—N1119.34 (13)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N(1)—H(4)···Cl(1)ii0.892.243.1210 (14)171
N(1)—H(5)···Cl(1)iii0.892.263.1291 (12)164
N(1)—H(6)···Cl(1)0.892.803.2460 (14)113
N(1)—H(6)···Cl(1)iv0.892.383.1521 (12)145
Symmetry codes: (ii) x, y+1/2, z1/2; (iii) x+1, y1/2, z+1/2; (iv) x+1, y+1/2, z+1/2.
 

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