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In the title compound, C8H14N22+·2Cl, the cation possesses a crystallographically imposed center of symmetry. The crystal packing is stabilized by inter­molecular N—H...Cl hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002619/cv2183sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002619/cv2183Isup2.hkl
Contains datablock I

CCDC reference: 636858

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.092
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2006) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

(p-Phenylenedimethylene)diammonium dichloride top
Crystal data top
C8H14N22+·2ClZ = 1
Mr = 209.12F(000) = 110
Triclinic, P1The final unit cell was obtained from the xyz centroids of 1454 reflections after integration using the SAINTPLUS software package (Bruker, 2000).
Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the finalatomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
Hall symbol: -P 1Dx = 1.405 Mg m3
a = 4.3496 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 5.809 (1) ÅCell parameters from 1454 reflections
c = 10.197 (2) Åθ = 3.6–29.2°
α = 101.836 (3)°µ = 0.61 mm1
β = 99.727 (3)°T = 100 K
γ = 93.800 (3)°Platelet, colourless
V = 247.18 (8) Å30.17 × 0.08 × 0.03 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
986 independent reflections
Radiation source: fine focus sealed Siemens Mo tube881 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.046
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.6°
φ and ω scansh = 55
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
k = 77
Tmin = 0.900, Tmax = 0.982l = 1212
1835 measured reflections
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.092All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0368P)2 + 0.28P]
where P = (Fo2 + 2Fc2)/3
986 reflections(Δ/σ)max < 0.001
83 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N0.5288 (5)0.1941 (3)0.8760 (2)0.0158 (6)
C10.2753 (5)0.1648 (4)0.7529 (2)0.0176 (7)
C20.3960 (5)0.0804 (4)0.6224 (2)0.0144 (6)
C30.5593 (5)0.2376 (4)0.5657 (2)0.0159 (6)
C40.3367 (5)0.1577 (4)0.5556 (2)0.0162 (6)
Cl0.15450 (13)0.29407 (9)0.12289 (5)0.0178 (2)
H10.108 (6)0.050 (5)0.761 (3)0.016 (6)*
H1'0.201 (7)0.320 (5)0.758 (3)0.025 (7)*
H30.599 (6)0.394 (5)0.612 (3)0.016 (6)*
H40.224 (6)0.268 (5)0.595 (3)0.018 (6)*
H50.669 (7)0.323 (5)0.884 (3)0.019 (7)*
H5'0.623 (6)0.057 (5)0.873 (3)0.015 (6)*
H5"0.433 (8)0.229 (6)0.951 (4)0.035 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0197 (10)0.0149 (10)0.0132 (10)0.0042 (8)0.0050 (8)0.0016 (8)
C10.0161 (12)0.0197 (12)0.0179 (12)0.0046 (9)0.0056 (9)0.0036 (9)
C20.0157 (11)0.0154 (10)0.0113 (10)0.0050 (8)0.0009 (8)0.0012 (8)
C30.0181 (11)0.0125 (10)0.0165 (12)0.0030 (8)0.0030 (9)0.0016 (9)
C40.0171 (11)0.0153 (11)0.0168 (11)0.0019 (8)0.0030 (9)0.0047 (9)
Cl0.0215 (3)0.0153 (3)0.0166 (3)0.0035 (2)0.0049 (2)0.0021 (2)
Geometric parameters (Å, º) top
N—C11.497 (3)C2—C41.397 (3)
N—H5"0.93 (4)C3—C4i1.390 (3)
N—H50.92 (3)C1—H10.98 (3)
N—H5'0.92 (3)C1—H1'0.97 (3)
C1—C21.513 (3)C3—H30.92 (3)
C2—C31.394 (3)C4—H40.97 (3)
Cl···Ni3.235 (2)C4···C2vi3.496 (3)
Cl···Nii3.190 (2)C3···H1'x3.08 (3)
Cl···Niii3.199 (2)C4···H3xi3.03 (3)
Cl···Niv3.310 (2)H1···H42.38 (4)
Cl···H1'v2.98 (3)H1···H5'ix2.56 (4)
Cl···H1vi2.80 (3)H1···Clvi2.80 (3)
Cl···H5'i2.32 (3)H1'···C3ix3.08 (3)
Cl···H5'iv3.14 (3)H1'···Clv2.98 (3)
Cl···H5"iii2.28 (4)H1'···H32.54 (4)
Cl···H5ii2.32 (3)H3···C4xii3.03 (3)
Cl···H5iv2.98 (3)H3···H1'2.54 (4)
Cl···H3ii2.92 (3)H3···Clii2.92 (3)
N···Clvii3.199 (2)H4···H12.38 (4)
N···Clviii3.310 (2)H5···Clviii2.98 (3)
N···Cli3.235 (2)H5···Clii2.32 (3)
N···Clii3.190 (2)H5'···Cli2.32 (3)
C1···C3ix3.467 (3)H5'···H1x2.56 (4)
C2···C4vi3.496 (3)H5'···Clviii3.14 (3)
C3···C1x3.467 (3)H5"···Clvii2.28 (4)
C1—N—H5'109.4 (18)C2—C4—C3i120.5 (2)
C1—N—H5"107 (2)N—C1—H1107.8 (17)
H5—N—H5'113 (3)N—C1—H1'104.9 (18)
H5—N—H5"105 (3)C2—C1—H1110.1 (17)
H5'—N—H5"112 (3)C2—C1—H1'111.9 (18)
C1—N—H5111.4 (18)H1—C1—H1'110 (2)
N—C1—C2111.66 (18)C2—C3—H3118.1 (18)
C1—C2—C3121.1 (2)C4i—C3—H3121.7 (18)
C1—C2—C4119.7 (2)C2—C4—H4119.5 (17)
C3—C2—C4119.27 (19)C3i—C4—H4120.0 (17)
C2—C3—C4i120.3 (2)
N—C1—C2—C380.4 (3)C1—C2—C4—C3i178.8 (2)
N—C1—C2—C4101.2 (2)C3—C2—C4—C3i0.4 (3)
C1—C2—C3—C4i178.8 (2)C2—C3—C4i—C2i0.4 (3)
C4—C2—C3—C4i0.4 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y, z1; (iv) x1, y, z1; (v) x, y+1, z+1; (vi) x, y, z+1; (vii) x, y, z+1; (viii) x+1, y, z+1; (ix) x1, y, z; (x) x+1, y, z; (xi) x, y1, z; (xii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H5···Clii0.92 (3)2.32 (3)3.190 (2)158 (3)
N—H5···Cli0.92 (3)2.32 (3)3.235 (2)176 (2)
N—H5"···Clvii0.93 (4)2.28 (4)3.199 (2)175 (4)
C1—H1···Clvi0.98 (3)2.80 (3)3.705 (2)154 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (vi) x, y, z+1; (vii) x, y, z+1.
 

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