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In the title compound, 2C8H12N+·C6Cl2O42−, the cation and the anion are held together by bifurcated N—H...O hydrogen bonds to give a centrosymmetric chloranilate–tri­methyl­pyridinium 1:2 unit. The 1:2 units are connected by C—H...O hydrogen bonds to form a molecular layer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025334/kp6006sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025334/kp6006Isup2.hkl
Contains datablock I

CCDC reference: 255895

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.122
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT333_ALERT_2_B Large Average Benzene C-C Dist. C1 -C3_a 1.47 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.35 PLAT335_ALERT_2_C Large Benzene C-C Range C1 -C3_a 0.16 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C3_a ... 1.54 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 4 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: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (MSC, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

(I) top
Crystal data top
2C8H12N+·C6Cl2O42Z = 1
Mr = 451.35F(000) = 236
Triclinic, P1Dx = 1.311 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4902 (9) ÅCell parameters from 25 reflections
b = 9.0205 (16) Åθ = 10.5–12.5°
c = 9.3236 (14) ŵ = 0.31 mm1
α = 115.456 (12)°T = 296 K
β = 112.034 (10)°Prism, brown
γ = 94.799 (13)°0.50 × 0.30 × 0.20 mm
V = 571.48 (18) Å3
Data collection top
Rigaku AFC-5R
diffractometer
1704 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.014
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
ω–2θ scansh = 1110
Absorption correction: ψ scan
(North et al., 1968)
k = 011
Tmin = 0.895, Tmax = 0.940l = 1210
2780 measured reflections3 standard reflections every 97 reflections
2615 independent reflections intensity decay: 0.5%
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.051P)2 + 0.175P]
where P = (Fo2 + 2Fc2)/3
2615 reflections(Δ/σ)max = 0.001
143 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

Experimental. The scan width was (1.68 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 3 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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
Cl0.97851 (9)0.90062 (9)0.12221 (8)0.0634 (2)
O10.7611 (2)0.7043 (2)0.2076 (2)0.0579 (5)
O21.2070 (3)1.2135 (2)0.4692 (2)0.0663 (5)
N0.6331 (3)0.4395 (3)0.2357 (2)0.0464 (5)
C10.8768 (3)0.8412 (3)0.3384 (3)0.0412 (5)
C20.9916 (3)0.9509 (3)0.3293 (3)0.0419 (5)
C31.1118 (3)1.1101 (3)0.4770 (3)0.0429 (5)
C40.4803 (3)0.4105 (3)0.2456 (3)0.0455 (5)
C50.4314 (3)0.2695 (3)0.2595 (3)0.0520 (6)
C60.5347 (3)0.1593 (3)0.2593 (3)0.0560 (6)
C70.6899 (4)0.1955 (4)0.2474 (4)0.0598 (7)
C80.7394 (3)0.3382 (3)0.2371 (3)0.0549 (6)
C90.3746 (3)0.5330 (3)0.2393 (4)0.0599 (7)
C100.4829 (5)0.0040 (4)0.2743 (5)0.0847 (10)
C110.9090 (4)0.3891 (4)0.2307 (5)0.0804 (9)
H10.674 (4)0.538 (4)0.240 (4)0.079 (9)*
H20.32770.24850.26910.062*
H30.76110.12250.24630.072*
H40.45330.64570.29530.090*
H50.30580.53520.30130.090*
H60.29650.49710.11720.090*
H70.36070.01870.25090.127*
H80.55670.02590.39250.127*
H90.49820.09370.18890.127*
H100.88140.38280.11820.121*
H110.97790.31250.24410.121*
H120.97600.50440.32580.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0733 (5)0.0690 (4)0.0382 (3)0.0015 (3)0.0299 (3)0.0191 (3)
O10.0672 (11)0.0474 (9)0.0398 (8)0.0093 (8)0.0225 (8)0.0125 (7)
O20.0780 (13)0.0580 (11)0.0489 (10)0.0155 (9)0.0323 (9)0.0188 (8)
N0.0471 (11)0.0403 (11)0.0424 (10)0.0022 (9)0.0198 (9)0.0154 (8)
C10.0460 (12)0.0375 (11)0.0368 (10)0.0066 (10)0.0197 (9)0.0163 (9)
C20.0486 (13)0.0441 (12)0.0324 (10)0.0066 (10)0.0217 (9)0.0170 (9)
C30.0458 (12)0.0452 (12)0.0394 (11)0.0076 (10)0.0228 (10)0.0207 (10)
C40.0416 (12)0.0468 (13)0.0366 (10)0.0039 (10)0.0155 (9)0.0152 (10)
C50.0436 (13)0.0593 (15)0.0512 (13)0.0050 (12)0.0208 (11)0.0286 (12)
C60.0552 (15)0.0554 (15)0.0538 (14)0.0085 (13)0.0198 (12)0.0300 (12)
C70.0578 (16)0.0583 (16)0.0697 (17)0.0219 (13)0.0308 (14)0.0347 (14)
C80.0510 (14)0.0575 (15)0.0517 (13)0.0111 (13)0.0274 (12)0.0210 (12)
C90.0544 (16)0.0568 (16)0.0662 (16)0.0159 (13)0.0267 (13)0.0296 (13)
C100.086 (2)0.079 (2)0.109 (3)0.0192 (18)0.043 (2)0.066 (2)
C110.068 (2)0.085 (2)0.108 (3)0.0268 (18)0.060 (2)0.047 (2)
Geometric parameters (Å, º) top
Cl—C21.739 (2)C6—C71.387 (4)
O1—C11.257 (3)C6—C101.512 (4)
O2—C31.227 (2)C7—C81.374 (4)
C1—C21.381 (3)C7—H30.93
C1—C3i1.543 (3)C8—C111.505 (3)
C2—C31.414 (3)C9—H40.96
C3—C1i1.543 (3)C9—H50.96
N—C81.338 (3)C9—H60.96
N—C41.347 (3)C10—H70.96
N—H10.91 (3)C10—H80.96
C4—C51.379 (3)C10—H90.96
C4—C91.487 (3)C11—H100.96
C5—C61.380 (4)C11—H110.96
C5—H20.93C11—H120.96
O1···N2.697 (3)O2···C4i3.327 (3)
O1···C113.260 (5)O2···C5iii3.345 (4)
O1···C9ii3.404 (3)O2···C9i3.360 (4)
O2···Ni2.880 (3)C2···C7iv3.597 (5)
C8—N—C4123.6 (2)C6—C7—H3119.7
C8—N—H1116.6 (19)N—C8—C7118.6 (2)
C4—N—H1119.5 (19)N—C8—C11117.9 (2)
O1—C1—C2125.42 (19)C7—C8—C11123.6 (3)
O1—C1—C3i116.55 (18)C4—C9—H4109.5
C2—C1—C3i118.03 (18)C4—C9—H5109.5
C1—C2—C3123.99 (18)C4—C9—H6109.5
C1—C2—Cl118.86 (16)H4—C9—H5109.5
C3—C2—Cl116.97 (15)H4—C9—H6109.5
O2—C3—C2124.79 (19)H5—C9—H6109.5
O2—C3—C1i117.33 (19)C6—C10—H7109.5
C2—C3—C1i117.87 (18)C6—C10—H8109.5
N—C4—C5118.2 (2)C6—C10—H9109.5
N—C4—C9117.4 (2)H7—C10—H8109.5
C5—C4—C9124.4 (2)H7—C10—H9109.5
C4—C5—C6120.7 (2)H8—C10—H9109.5
C4—C5—H2119.7C8—C11—H10109.5
C6—C5—H2119.7C8—C11—H11109.5
C5—C6—C7118.3 (2)C8—C11—H12109.5
C5—C6—C10121.3 (2)H10—C11—H11109.5
C7—C6—C10120.4 (3)H10—C11—H12109.5
C8—C7—C6120.6 (3)H11—C11—H12109.5
C8—C7—H3119.7
O1—C1—C2—C3175.3 (2)N—C4—C5—C61.4 (3)
C3i—C1—C2—C33.9 (4)C9—C4—C5—C6178.1 (2)
O1—C1—C2—Cl0.3 (3)C4—C5—C6—C70.9 (4)
C3i—C1—C2—Cl178.84 (17)C4—C5—C6—C10179.9 (3)
C1—C2—C3—O2175.5 (2)C5—C6—C7—C80.4 (4)
Cl—C2—C3—O20.4 (3)C10—C6—C7—C8178.8 (3)
C1—C2—C3—C1i3.9 (4)C4—N—C8—C70.7 (4)
Cl—C2—C3—C1i178.92 (17)C4—N—C8—C11178.2 (2)
C8—N—C4—C50.5 (3)C6—C7—C8—N1.2 (4)
C8—N—C4—C9179.0 (2)C6—C7—C8—C11177.7 (3)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+1, z; (iii) x+1, y+1, z; (iv) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1···O10.91 (4)1.81 (4)2.697 (3)168 (3)
N—H1···O2i0.91 (4)2.40 (3)2.880 (3)114 (2)
C5—H2···O2v0.932.553.345 (4)143
C9—H6···O1ii0.962.593.404 (3)142
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+1, z; (v) x1, y1, z.
 

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