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In the crystal structure of the title compound, C16H16N42+·2C l·6H2O, the 2,2′-(p-phenyl­enediimino)­dipyrid­inium cation has inversion symmetry. The chloride ions and water mol­ecules are linked via O—H...O and O—H...Cl hydrogen bonds into an infinite two-dimensional network parallel to the (001) plane. The cations, as fourfold hydrogen-bond donors, connect neighbouring [Cl·(H2O)3] anionic networks into polymeric three-dimensional hydrogen-bonded assemblies.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026687/kp2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026687/kp2032Isup2.hkl
Contains datablock I

CCDC reference: 618256

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.101
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 5 Cl
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2000); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97.

2,2'-(p-Phenylenediimino)dipyridinium dichloride hexahydrate top
Crystal data top
C16H16N42+·2Cl·6H2OZ = 1
Mr = 443.32F(000) = 234
Triclinic, P1Dx = 1.326 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 8.287 (1) ÅCell parameters from 3148 reflections
b = 8.3104 (10) Åθ = 4–50°
c = 9.1906 (12) ŵ = 0.33 mm1
α = 65.572 (12)°T = 170 K
β = 89.03 (1)°Block, colourless
γ = 75.472 (10)°0.40 × 0.40 × 0.40 mm
V = 555.14 (14) Å3
Data collection top
Kuma KM4CCD κ-geometry
diffractometer
1757 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
ω scansh = 99
3011 measured reflectionsk = 89
1942 independent reflectionsl = 710
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Only H-atom displacement parameters refined
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0572P)2 + 0.1307P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1942 reflectionsΔρmax = 0.21 e Å3
142 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.064 (10)
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
Cl10.47095 (6)0.69261 (6)0.37170 (5)0.0521 (2)
O1W0.91574 (17)0.76384 (19)0.24879 (17)0.0567 (4)
H1WA0.85210.80090.30850.064 (7)*
H1WB1.01510.71910.29460.081 (8)*
O2W0.74753 (17)0.8964 (2)0.45752 (18)0.0625 (4)
H2WA0.66960.84910.50160.085 (9)*
H2WB0.69871.01010.42330.084 (8)*
O3W1.2306 (2)0.6093 (3)0.4144 (2)0.0921 (6)
H3WA1.30520.53680.38920.103 (10)*
H3WB1.27830.65730.46070.100 (10)*
N10.84355 (16)0.51561 (18)0.15843 (16)0.0378 (3)
H10.84210.61140.18110.050 (5)*
N20.63319 (18)0.68630 (18)0.05458 (17)0.0419 (4)
H20.58900.68650.14340.051 (5)*
C20.74674 (19)0.5294 (2)0.03585 (19)0.0358 (4)
C30.7710 (2)0.3748 (2)0.0016 (2)0.0442 (4)
H30.70520.38730.08930.043 (5)*
C40.8864 (3)0.2162 (2)0.0954 (2)0.0528 (5)
H40.90270.11490.06670.076 (7)*
C50.9808 (2)0.2050 (3)0.2259 (2)0.0561 (5)
H51.06630.09670.29140.066 (6)*
C60.9575 (2)0.3561 (2)0.2536 (2)0.0469 (4)
H61.01500.36330.33960.051 (5)*
C70.57099 (18)0.8438 (2)0.02286 (19)0.0346 (4)
C80.5463 (2)1.0151 (2)0.14945 (18)0.0381 (4)
H80.57951.02690.25320.041 (5)*
C90.5243 (2)0.8280 (2)0.12679 (19)0.0385 (4)
H90.53750.70990.21480.042 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0556 (3)0.0532 (3)0.0520 (3)0.0122 (2)0.0034 (2)0.0279 (2)
O1W0.0517 (8)0.0581 (8)0.0702 (9)0.0110 (6)0.0024 (7)0.0387 (7)
O2W0.0499 (8)0.0557 (9)0.0730 (10)0.0029 (7)0.0018 (7)0.0249 (7)
O3W0.0505 (9)0.1292 (16)0.1248 (16)0.0013 (9)0.0109 (9)0.0943 (14)
N10.0353 (7)0.0325 (7)0.0443 (7)0.0067 (5)0.0032 (6)0.0163 (6)
N20.0464 (8)0.0365 (7)0.0424 (8)0.0011 (6)0.0048 (6)0.0217 (6)
C20.0351 (8)0.0335 (8)0.0399 (8)0.0094 (6)0.0088 (6)0.0167 (7)
C30.0495 (10)0.0386 (9)0.0510 (10)0.0140 (7)0.0119 (8)0.0243 (8)
C40.0598 (12)0.0336 (9)0.0659 (12)0.0100 (8)0.0212 (9)0.0240 (8)
C50.0505 (11)0.0381 (10)0.0617 (12)0.0004 (8)0.0085 (9)0.0108 (9)
C60.0375 (9)0.0441 (10)0.0483 (10)0.0033 (7)0.0013 (7)0.0133 (8)
C70.0305 (7)0.0335 (8)0.0396 (8)0.0031 (6)0.0026 (6)0.0182 (7)
C80.0395 (8)0.0402 (9)0.0314 (8)0.0049 (7)0.0010 (6)0.0152 (7)
C90.0412 (9)0.0319 (8)0.0354 (8)0.0055 (6)0.0012 (6)0.0099 (6)
Geometric parameters (Å, º) top
O1W—H1WA0.8500C3—C41.361 (3)
O1W—H1WB0.8500C3—H30.9600
O2W—H2WA0.8500C4—C51.401 (3)
O2W—H2WB0.8500C4—H40.9600
O3W—H3WA0.8500C5—C61.349 (3)
O3W—H3WB0.8500C5—H50.9600
N1—C21.343 (2)C6—H60.9600
N1—C61.362 (2)C7—C91.384 (2)
N1—H10.8999C7—C81.384 (2)
N2—C21.338 (2)C8—C9i1.387 (2)
N2—C71.4264 (19)C8—H80.9600
N2—H20.9001C9—C8i1.387 (2)
C2—C31.411 (2)C9—H90.9600
H1WA—O1W—H1WB108.7C5—C4—H4121.8
H2WA—O2W—H2WB101.2C6—C5—C4118.49 (17)
H3WA—O3W—H3WB108.9C6—C5—H5119.0
C2—N1—C6122.08 (15)C4—C5—H5122.4
C2—N1—H1123.0C5—C6—N1121.01 (17)
C6—N1—H1114.8C5—C6—H6125.3
C2—N2—C7128.24 (13)N1—C6—H6113.7
C2—N2—H2113.6C9—C7—C8120.19 (14)
C7—N2—H2118.1C9—C7—N2121.54 (14)
N2—C2—N1121.28 (14)C8—C7—N2118.09 (14)
N2—C2—C3120.54 (15)C7—C8—C9i120.17 (14)
N1—C2—C3118.15 (15)C7—C8—H8120.6
C4—C3—C2119.70 (17)C9i—C8—H8119.3
C4—C3—H3122.5C7—C9—C8i119.64 (15)
C2—C3—H3117.7C7—C9—H9121.1
C3—C4—C5120.49 (16)C8i—C9—H9119.3
C3—C4—H4117.7
C7—N2—C2—N113.8 (3)C4—C5—C6—N10.8 (3)
C7—N2—C2—C3168.02 (16)C2—N1—C6—C51.6 (3)
C6—N1—C2—N2178.72 (15)C2—N2—C7—C945.1 (2)
C6—N1—C2—C33.0 (2)C2—N2—C7—C8139.67 (17)
N2—C2—C3—C4179.64 (16)C9—C7—C8—C9i0.4 (3)
N1—C2—C3—C42.1 (2)N2—C7—C8—C9i175.73 (14)
C2—C3—C4—C50.2 (3)C8—C7—C9—C8i0.4 (3)
C3—C4—C5—C61.6 (3)N2—C7—C9—C8i175.56 (14)
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O2W0.851.942.779 (2)168
O1W—H1WB···O3W0.851.912.759 (2)175
O2W—H2WA···Cl1ii0.852.353.1957 (17)175
O2W—H2WB···Cl1i0.852.373.2067 (16)168
O3W—H3WA···Cl1iii0.852.363.1986 (17)169
O3W—H3WB···Cl1iv0.852.393.2036 (17)161
N1—H1···O1W0.901.852.7121 (18)160
N2—H2···Cl10.902.313.2056 (15)179
Symmetry codes: (i) x+1, y+2, z; (ii) x, y, z+1; (iii) x+2, y+1, z; (iv) x+1, y, z+1.
 

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