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The cation of the title compound, C26H28N42+.2 Cl·4H2O, is centrosymmetric while the two Cl anions are each located on a twofold rotation axis. Hydrogen-bonding and π–π stacking inter­actions help to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011774/xu2204sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011774/xu2204Isup2.hkl
Contains datablock I

CCDC reference: 643139

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.120
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,2'-[3,3'-Dimethylbiphenyl-4,4'-diylbis(iminomethylene)]dipyridinium dichloride tetrahydrate top
Crystal data top
C26H28N42+·2Cl·4H2OF(000) = 1144
Mr = 539.49Dx = 1.277 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3113 reflections
a = 16.9526 (18) Åθ = 1.9–25.0°
b = 13.5920 (14) ŵ = 0.27 mm1
c = 12.3297 (18) ÅT = 294 K
β = 99.087 (8)°Prism, light yellow
V = 2805.4 (6) Å30.23 × 0.18 × 0.15 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer
2515 independent reflections
Radiation source: fine-focus sealed tube2011 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1920
Tmin = 0.921, Tmax = 0.961k = 1616
14917 measured reflectionsl = 1414
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0634P)2 + 1.0651P]
where P = (Fo2 + 2Fc2)/3
2515 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.24 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.

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
Cl10.50000.50789 (6)0.25000.0706 (3)
Cl20.00000.36762 (5)0.25000.0697 (3)
N10.15605 (10)0.52981 (12)0.27565 (12)0.0570 (4)
H1A0.10560.51900.27020.068*
N20.30775 (10)0.54721 (13)0.51192 (13)0.0573 (4)
H20.34140.50980.48650.069*
O1W0.41379 (9)0.42469 (12)0.43758 (13)0.0763 (5)
H1E0.44790.44860.39230.092*
H1F0.44280.38530.47450.092*
O2W0.52903 (11)0.31458 (12)0.59388 (14)0.0805 (5)
H2E0.52660.36020.64600.097*
H2F0.51320.26450.62800.097*
C10.15665 (10)0.69236 (12)0.03840 (13)0.0394 (4)
H10.11980.71770.01870.047*
C20.23665 (9)0.71838 (11)0.04299 (12)0.0349 (4)
C30.28902 (11)0.68093 (13)0.13193 (14)0.0460 (4)
H30.34290.69750.13980.055*
C40.26312 (11)0.61987 (14)0.20868 (14)0.0478 (4)
H40.29990.59670.26710.057*
C50.18348 (10)0.59230 (12)0.20065 (13)0.0417 (4)
C60.12875 (10)0.63131 (12)0.11333 (13)0.0428 (4)
C70.04124 (12)0.6071 (2)0.10085 (18)0.0742 (7)
H7A0.03450.53700.10290.111*
H7B0.01450.63210.03190.111*
H7C0.01880.63670.15980.111*
C80.20971 (13)0.48277 (14)0.36212 (15)0.0564 (5)
H8A0.25770.46300.33420.068*
H8B0.18450.42390.38510.068*
C90.23250 (11)0.54906 (14)0.46021 (14)0.0493 (5)
C100.17997 (13)0.60997 (18)0.50172 (17)0.0651 (6)
H100.12720.61390.46690.078*
C110.20475 (15)0.66542 (18)0.59464 (19)0.0731 (6)
H110.16860.70570.62290.088*
C120.28234 (15)0.66113 (18)0.64502 (19)0.0706 (6)
H120.29980.69850.70740.085*
C130.33349 (14)0.60118 (19)0.60214 (18)0.0725 (6)
H130.38660.59730.63530.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0783 (6)0.0749 (5)0.0598 (4)0.0000.0144 (4)0.000
Cl20.0690 (5)0.0507 (4)0.0876 (6)0.0000.0070 (4)0.000
N10.0511 (10)0.0721 (11)0.0466 (8)0.0136 (8)0.0043 (7)0.0200 (8)
N20.0503 (10)0.0708 (11)0.0517 (9)0.0126 (8)0.0103 (8)0.0091 (8)
O1W0.0650 (10)0.0779 (10)0.0922 (11)0.0149 (8)0.0311 (8)0.0180 (9)
O2W0.0951 (13)0.0729 (10)0.0759 (10)0.0016 (9)0.0208 (9)0.0031 (8)
C10.0394 (9)0.0443 (9)0.0342 (8)0.0002 (7)0.0046 (7)0.0031 (7)
C20.0374 (9)0.0363 (8)0.0315 (7)0.0012 (7)0.0067 (6)0.0025 (6)
C30.0365 (9)0.0607 (11)0.0403 (9)0.0058 (8)0.0042 (7)0.0073 (8)
C40.0424 (10)0.0616 (11)0.0376 (9)0.0012 (8)0.0007 (7)0.0116 (8)
C50.0468 (10)0.0448 (9)0.0341 (8)0.0040 (7)0.0083 (7)0.0022 (7)
C60.0399 (9)0.0504 (10)0.0382 (8)0.0063 (7)0.0069 (7)0.0021 (7)
C70.0467 (12)0.1106 (19)0.0631 (13)0.0178 (12)0.0014 (10)0.0302 (12)
C80.0660 (13)0.0578 (11)0.0461 (10)0.0037 (10)0.0105 (9)0.0155 (9)
C90.0485 (11)0.0580 (11)0.0424 (9)0.0033 (9)0.0102 (8)0.0181 (8)
C100.0473 (12)0.0845 (15)0.0633 (13)0.0123 (10)0.0080 (10)0.0070 (11)
C110.0727 (16)0.0805 (15)0.0692 (14)0.0180 (12)0.0210 (12)0.0034 (12)
C120.0761 (16)0.0774 (14)0.0569 (12)0.0060 (12)0.0064 (11)0.0028 (11)
C130.0597 (14)0.0901 (17)0.0627 (13)0.0086 (12)0.0055 (11)0.0017 (12)
Geometric parameters (Å, º) top
N1—C51.389 (2)C4—H40.9300
N1—C81.437 (2)C5—C61.409 (2)
N1—H1A0.8600C6—C71.504 (3)
N2—C91.333 (2)C7—H7A0.9600
N2—C131.346 (3)C7—H7B0.9600
N2—H20.8600C7—H7C0.9600
O1W—H1E0.9239C8—C91.509 (3)
O1W—H1F0.8158C8—H8A0.9700
O2W—H2E0.8986C8—H8B0.9700
O2W—H2F0.8651C9—C101.373 (3)
C1—C61.380 (2)C10—C111.380 (3)
C1—C21.394 (2)C10—H100.9300
C1—H10.9300C11—C121.364 (3)
C2—C31.394 (2)C11—H110.9300
C2—C2i1.490 (3)C12—C131.357 (3)
C3—C41.381 (2)C12—H120.9300
C3—H30.9300C13—H130.9300
C4—C51.390 (2)
C5—N1—C8121.78 (16)C6—C7—H7B109.5
C5—N1—H1A119.1H7A—C7—H7B109.5
C8—N1—H1A119.1C6—C7—H7C109.5
C9—N2—C13123.07 (18)H7A—C7—H7C109.5
C9—N2—H2118.5H7B—C7—H7C109.5
C13—N2—H2118.5N1—C8—C9112.39 (16)
H1E—O1W—H1F100.8N1—C8—H8A109.1
H2E—O2W—H2F98.2C9—C8—H8A109.1
C6—C1—C2124.02 (15)N1—C8—H8B109.1
C6—C1—H1118.0C9—C8—H8B109.1
C2—C1—H1118.0H8A—C8—H8B107.9
C3—C2—C1115.73 (14)N2—C9—C10117.46 (19)
C3—C2—C2i122.91 (18)N2—C9—C8118.47 (17)
C1—C2—C2i121.36 (17)C10—C9—C8124.05 (19)
C4—C3—C2121.77 (16)C9—C10—C11120.6 (2)
C4—C3—H3119.1C9—C10—H10119.7
C2—C3—H3119.1C11—C10—H10119.7
C3—C4—C5121.57 (16)C12—C11—C10120.0 (2)
C3—C4—H4119.2C12—C11—H11120.0
C5—C4—H4119.2C10—C11—H11120.0
N1—C5—C4122.76 (15)C13—C12—C11118.5 (2)
N1—C5—C6119.31 (15)C13—C12—H12120.7
C4—C5—C6117.91 (15)C11—C12—H12120.7
C1—C6—C5118.94 (15)N2—C13—C12120.4 (2)
C1—C6—C7120.01 (16)N2—C13—H13119.8
C5—C6—C7121.05 (15)C12—C13—H13119.8
C6—C7—H7A109.5
C6—C1—C2—C31.9 (2)N1—C5—C6—C70.6 (3)
C6—C1—C2—C2i177.64 (18)C4—C5—C6—C7178.36 (19)
C1—C2—C3—C41.6 (2)C5—N1—C8—C982.5 (2)
C2i—C2—C3—C4177.90 (18)C13—N2—C9—C100.6 (3)
C2—C3—C4—C50.3 (3)C13—N2—C9—C8177.89 (18)
C8—N1—C5—C45.2 (3)N1—C8—C9—N2140.48 (17)
C8—N1—C5—C6175.90 (17)N1—C8—C9—C1041.2 (2)
C3—C4—C5—N1178.97 (17)N2—C9—C10—C111.1 (3)
C3—C4—C5—C62.1 (3)C8—C9—C10—C11177.28 (19)
C2—C1—C6—C50.2 (3)C9—C10—C11—C121.0 (4)
C2—C1—C6—C7179.61 (18)C10—C11—C12—C130.4 (4)
N1—C5—C6—C1179.20 (16)C9—N2—C13—C120.0 (3)
C4—C5—C6—C11.9 (2)C11—C12—C13—N20.1 (4)
Symmetry code: (i) x+1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl20.862.713.4196 (18)140
N2—H2···O1W0.861.862.714 (2)177
O1W—H1E···Cl10.922.243.1355 (17)164
O1W—H1F···O2W0.822.132.929 (2)166
O2W—H2E···Cl1ii0.902.293.1732 (18)167
O2W—H2F···Cl2iii0.862.383.2217 (18)166
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+1/2, y+1/2, z+1.
 

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