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The title compound, (C10H16N)2[PdCl4], has been crystallized from acetonitrile. The asymmetric unit contains two 1-butyl-4-methyl­pyridinium cations in general positions and two halves of tetra­chloro­palladate(II) anions, with the metal atoms lying on inversion centers. The Pd atoms are four-coordinated in a slightly distorted square-planar geometry. The crystal structure is stabilized by numerous weak C—H...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013912/bt2036sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013912/bt2036Isup2.hkl
Contains datablock I

CCDC reference: 608371

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.099
  • Data-to-parameter ratio = 43.2

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C25 PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. CL11 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. CL21 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. CL21 .. 2.94 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16B .. CL12 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H20 .. CL22 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H23 .. CL11 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H23 .. CL12 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H24 .. CL11 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H26A .. CL21 .. 2.84 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H26A .. CL22 .. 2.85 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 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 11 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Bis(1-butyl-4-methylpyridinium) tetrachloropalladate(II) top
Crystal data top
(C10H16N)2[PdCl4]Z = 2
Mr = 548.68F(000) = 560
Triclinic, P1Dx = 1.462 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.710 (3) ÅCell parameters from 22310 reflections
b = 8.818 (3) Åθ = 4.8–35.0°
c = 16.354 (5) ŵ = 1.18 mm1
α = 95.54 (3)°T = 100 K
β = 94.03 (3)°Block, red–brown
γ = 90.99 (3)°0.18 × 0.15 × 0.11 mm
V = 1246.7 (7) Å3
Data collection top
Kuma KM-4 CCD
diffractometer
10839 independent reflections
Radiation source: fine-focus sealed tube8173 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 35.0°, θmin = 4.2°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 1412
Tmin = 0.819, Tmax = 0.903k = 1414
28914 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.5036P]
where P = (Fo2 + 2Fc2)/3
10839 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 2.52 e Å3
0 restraintsΔρmin = 1.32 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
Pd10.50000.50000.00000.01238 (5)
Pd20.50000.50000.50000.01214 (5)
Cl110.55327 (6)0.49695 (5)0.13945 (3)0.01732 (9)
Cl120.31709 (5)0.30693 (5)0.00210 (3)0.01813 (9)
Cl210.52687 (5)0.49036 (5)0.35986 (3)0.01676 (8)
Cl220.30175 (5)0.32022 (5)0.47753 (3)0.01771 (9)
N100.5608 (2)0.03945 (19)0.17362 (10)0.0187 (3)
C100.5545 (2)0.1105 (2)0.18625 (13)0.0207 (4)
H100.58870.18450.14590.025*
C110.4991 (3)0.1563 (2)0.25676 (13)0.0218 (4)
H110.49600.26150.26490.026*
C120.4470 (2)0.0487 (2)0.31679 (13)0.0211 (4)
C130.4542 (3)0.1044 (2)0.30204 (13)0.0230 (4)
H130.41910.18030.34120.028*
C140.5122 (3)0.1460 (2)0.23074 (13)0.0223 (4)
H140.51800.25070.22170.027*
C150.3865 (3)0.0977 (3)0.39388 (15)0.0307 (5)
H15A0.46600.15300.42330.046*
H15B0.29540.16440.37960.046*
H15C0.35830.00770.42910.046*
C160.6275 (3)0.0888 (2)0.09898 (12)0.0220 (4)
H16A0.56340.16960.07730.026*
H16B0.62480.00140.05600.026*
C170.7924 (3)0.1488 (3)0.11639 (14)0.0261 (4)
H17A0.82740.18680.06570.031*
H17B0.79390.23640.15910.031*
C180.9061 (3)0.0327 (3)0.14502 (16)0.0293 (5)
H18A0.89800.05950.10520.035*
H18B0.87840.00270.19900.035*
C191.0735 (3)0.0935 (4)0.15335 (19)0.0422 (7)
H19A1.10590.11160.09890.063*
H19B1.14030.01850.17720.063*
H19C1.08080.18930.18930.063*
N200.00894 (19)0.5087 (2)0.31236 (10)0.0190 (3)
C200.1409 (2)0.5029 (3)0.29500 (13)0.0222 (4)
H200.21500.46480.33270.027*
C210.1857 (2)0.5522 (3)0.22285 (14)0.0236 (4)
H210.29090.54810.21110.028*
C220.0783 (2)0.6080 (2)0.16674 (13)0.0208 (4)
C230.0743 (2)0.6131 (3)0.18684 (13)0.0232 (4)
H230.15040.65170.15040.028*
C240.1152 (2)0.5623 (3)0.25949 (13)0.0234 (4)
H240.21980.56510.27240.028*
C250.1250 (3)0.6590 (3)0.08688 (14)0.0275 (4)
H25A0.16970.57350.05460.041*
H25B0.03440.69410.05570.041*
H25C0.20140.74260.09820.041*
C260.0576 (2)0.4386 (3)0.38560 (12)0.0221 (4)
H26A0.15270.48660.40420.026*
H26B0.02380.45590.43110.026*
C270.0864 (3)0.2701 (3)0.36409 (13)0.0244 (4)
H27A0.00910.22380.34510.029*
H27B0.16670.25450.31790.029*
C280.1375 (3)0.1886 (3)0.43595 (15)0.0315 (5)
H28A0.24020.22440.45040.038*
H28B0.06410.21380.48460.038*
C290.1450 (3)0.0164 (3)0.41395 (18)0.0385 (6)
H29A0.04380.01870.39870.058*
H29B0.22140.00890.36750.058*
H29C0.17470.03390.46160.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01328 (9)0.01129 (8)0.01248 (8)0.00079 (6)0.00137 (6)0.00023 (6)
Pd20.01148 (9)0.01208 (8)0.01270 (8)0.00048 (6)0.00051 (6)0.00058 (6)
Cl110.0233 (2)0.01607 (19)0.01254 (18)0.00004 (15)0.00081 (15)0.00154 (14)
Cl120.0177 (2)0.01607 (19)0.0203 (2)0.00343 (15)0.00228 (15)0.00057 (15)
Cl210.0172 (2)0.0204 (2)0.01269 (18)0.00074 (15)0.00102 (14)0.00196 (15)
Cl220.0155 (2)0.0170 (2)0.0202 (2)0.00332 (15)0.00197 (15)0.00081 (15)
N100.0231 (8)0.0156 (7)0.0176 (7)0.0024 (6)0.0022 (6)0.0017 (6)
C100.0274 (10)0.0125 (8)0.0219 (9)0.0016 (7)0.0031 (7)0.0004 (7)
C110.0280 (10)0.0136 (8)0.0242 (9)0.0014 (7)0.0049 (8)0.0022 (7)
C120.0247 (10)0.0173 (9)0.0217 (9)0.0010 (7)0.0045 (7)0.0019 (7)
C130.0310 (11)0.0151 (9)0.0233 (10)0.0029 (7)0.0074 (8)0.0004 (7)
C140.0282 (10)0.0147 (8)0.0240 (10)0.0018 (7)0.0040 (8)0.0010 (7)
C150.0436 (14)0.0232 (10)0.0271 (11)0.0014 (9)0.0141 (10)0.0042 (9)
C160.0331 (11)0.0180 (9)0.0158 (8)0.0038 (8)0.0028 (7)0.0039 (7)
C170.0352 (12)0.0214 (10)0.0225 (10)0.0029 (8)0.0075 (8)0.0030 (8)
C180.0269 (11)0.0264 (11)0.0344 (12)0.0018 (9)0.0057 (9)0.0001 (9)
C190.0293 (13)0.0463 (16)0.0495 (17)0.0106 (11)0.0097 (11)0.0061 (13)
N200.0152 (7)0.0234 (8)0.0182 (7)0.0016 (6)0.0005 (6)0.0020 (6)
C200.0135 (8)0.0274 (10)0.0257 (10)0.0016 (7)0.0007 (7)0.0040 (8)
C210.0145 (9)0.0277 (10)0.0294 (10)0.0016 (7)0.0035 (7)0.0058 (8)
C220.0205 (9)0.0199 (9)0.0228 (9)0.0017 (7)0.0045 (7)0.0034 (7)
C230.0177 (9)0.0297 (11)0.0232 (10)0.0030 (8)0.0009 (7)0.0080 (8)
C240.0159 (9)0.0314 (11)0.0235 (10)0.0035 (8)0.0005 (7)0.0068 (8)
C250.0277 (11)0.0294 (11)0.0271 (11)0.0037 (9)0.0084 (8)0.0069 (9)
C260.0203 (9)0.0306 (11)0.0156 (8)0.0037 (8)0.0012 (7)0.0032 (7)
C270.0241 (10)0.0306 (11)0.0189 (9)0.0013 (8)0.0010 (7)0.0055 (8)
C280.0301 (12)0.0399 (14)0.0274 (11)0.0026 (10)0.0064 (9)0.0145 (10)
C290.0360 (14)0.0386 (14)0.0435 (15)0.0057 (11)0.0020 (11)0.0195 (12)
Geometric parameters (Å, º) top
Pd1—Cl112.2979 (8)C18—H18B0.9900
Pd1—Cl11i2.2979 (8)C19—H19A0.9800
Pd1—Cl122.3158 (9)C19—H19B0.9800
Pd1—Cl12i2.3158 (9)C19—H19C0.9800
Pd2—Cl212.3136 (8)N20—C201.355 (3)
Pd2—Cl21ii2.3136 (8)N20—C241.345 (3)
Pd2—Cl222.3095 (9)N20—C261.484 (3)
Pd2—Cl22ii2.3095 (9)C20—C211.375 (3)
N10—C101.358 (3)C20—H200.9500
N10—C141.355 (3)C21—C221.394 (3)
N10—C161.486 (3)C21—H210.9500
C10—C111.374 (3)C22—C231.391 (3)
C10—H100.9500C22—C251.502 (3)
C11—C121.402 (3)C23—C241.377 (3)
C11—H110.9500C23—H230.9500
C12—C131.395 (3)C24—H240.9500
C12—C151.498 (3)C25—H25A0.9800
C13—C141.381 (3)C25—H25B0.9800
C13—H130.9500C25—H25C0.9800
C14—H140.9500C26—C271.507 (3)
C15—H15A0.9800C26—H26A0.9900
C15—H15B0.9800C26—H26B0.9900
C15—H15C0.9800C27—C281.523 (3)
C16—C171.521 (3)C27—H27A0.9900
C16—H16A0.9900C27—H27B0.9900
C16—H16B0.9900C28—C291.526 (4)
C17—C181.520 (3)C28—H28A0.9900
C17—H17A0.9900C28—H28B0.9900
C17—H17B0.9900C29—H29A0.9800
C18—C191.536 (4)C29—H29B0.9800
C18—H18A0.9900C29—H29C0.9800
Cl11—Pd1—Cl11i180.0C18—C19—H19A109.5
Cl11—Pd1—Cl12i90.29 (3)C18—C19—H19B109.5
Cl11i—Pd1—Cl12i89.71 (3)H19A—C19—H19B109.5
Cl11—Pd1—Cl1289.71 (3)C18—C19—H19C109.5
Cl11i—Pd1—Cl1290.29 (3)H19A—C19—H19C109.5
Cl12i—Pd1—Cl12180.0H19B—C19—H19C109.5
Cl22ii—Pd2—Cl22180.0C20—N20—C24120.6 (2)
Cl22ii—Pd2—Cl2189.47 (3)C20—N20—C26119.1 (2)
Cl22—Pd2—Cl2190.53 (3)C24—N20—C26119.9 (2)
Cl22ii—Pd2—Cl21ii90.53 (3)N20—C20—C21120.1 (2)
Cl22—Pd2—Cl21ii89.47 (3)N20—C20—H20119.9
Cl21—Pd2—Cl21ii180.0C21—C20—H20119.9
C10—N10—C14120.2 (2)C20—C21—C22120.7 (2)
C10—N10—C16120.5 (2)C20—C21—H21119.7
C14—N10—C16119.3 (2)C22—C21—H21119.7
N10—C10—C11120.8 (2)C23—C22—C21117.6 (2)
N10—C10—H10119.6C23—C22—C25121.1 (2)
C11—C10—H10119.6C21—C22—C25121.2 (2)
C10—C11—C12120.4 (2)C24—C23—C22120.1 (2)
C10—C11—H11119.8C24—C23—H23119.9
C12—C11—H11119.8C22—C23—H23119.9
C13—C12—C11117.6 (2)N20—C24—C23120.9 (2)
C13—C12—C15121.6 (2)N20—C24—H24119.6
C11—C12—C15120.8 (2)C23—C24—H24119.6
C14—C13—C12120.2 (2)C22—C25—H25A109.5
C14—C13—H13119.9C22—C25—H25B109.5
C12—C13—H13119.9H25A—C25—H25B109.5
N10—C14—C13120.8 (2)C22—C25—H25C109.5
N10—C14—H14119.6H25A—C25—H25C109.5
C13—C14—H14119.6H25B—C25—H25C109.5
C12—C15—H15A109.5N20—C26—C27109.6 (2)
C12—C15—H15B109.5N20—C26—H26A109.7
H15A—C15—H15B109.5C27—C26—H26A109.7
C12—C15—H15C109.5N20—C26—H26B109.7
H15A—C15—H15C109.5C27—C26—H26B109.7
H15B—C15—H15C109.5H26A—C26—H26B108.2
N10—C16—C17112.4 (2)C26—C27—C28113.2 (2)
N10—C16—H16A109.1C26—C27—H27A108.9
C17—C16—H16A109.1C28—C27—H27A108.9
N10—C16—H16B109.1C26—C27—H27B108.9
C17—C16—H16B109.1C28—C27—H27B108.9
H16A—C16—H16B107.9H27A—C27—H27B107.7
C18—C17—C16114.8 (2)C27—C28—C29110.8 (2)
C18—C17—H17A108.6C27—C28—H28A109.5
C16—C17—H17A108.6C29—C28—H28A109.5
C18—C17—H17B108.6C27—C28—H28B109.5
C16—C17—H17B108.6C29—C28—H28B109.5
H17A—C17—H17B107.5H28A—C28—H28B108.1
C17—C18—C19112.9 (2)C28—C29—H29A109.5
C17—C18—H18A109.0C28—C29—H29B109.5
C19—C18—H18A109.0H29A—C29—H29B109.5
C17—C18—H18B109.0C28—C29—H29C109.5
C19—C18—H18B109.0H29A—C29—H29C109.5
H18A—C18—H18B107.8H29B—C29—H29C109.5
C14—N10—C10—C110.0 (3)C24—N20—C20—C210.1 (3)
C16—N10—C10—C11177.2 (2)C26—N20—C20—C21173.0 (2)
N10—C10—C11—C120.4 (3)N20—C20—C21—C220.2 (3)
C10—C11—C12—C130.1 (3)C20—C21—C22—C230.5 (3)
C10—C11—C12—C15180.0 (2)C20—C21—C22—C25178.6 (2)
C11—C12—C13—C140.5 (3)C21—C22—C23—C240.8 (3)
C15—C12—C13—C14179.3 (2)C25—C22—C23—C24178.4 (2)
C10—N10—C14—C130.6 (3)C20—N20—C24—C230.3 (3)
C16—N10—C14—C13177.9 (2)C26—N20—C24—C23173.2 (2)
C12—C13—C14—N100.9 (3)C22—C23—C24—N200.7 (3)
C14—N10—C16—C1777.4 (2)C24—N20—C26—C2789.8 (2)
C10—N10—C16—C1799.8 (2)C20—N20—C26—C2783.2 (2)
N10—C16—C17—C1862.5 (2)N20—C26—C27—C28179.9 (2)
C16—C17—C18—C19174.2 (2)C26—C27—C28—C29172.8 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···CL11iii0.952.813.472 (3)127
C10—H10···CL12iv0.952.743.642 (3)159
C11—H11···CL11iii0.952.893.507 (3)124
C11—H11···CL21iii0.952.813.687 (3)154
C13—H13···CL210.952.863.478 (3)124
C13—H13···CL220.952.723.632 (3)162
C14—H14···CL110.952.693.586 (3)158
C14—H14···CL210.952.943.522 (3)121
C16—H16A···CL120.992.753.699 (3)160
C16—H16B···CL12iv0.992.863.768 (3)153
C20—H20···CL210.952.723.461 (3)135
C20—H20···CL220.952.863.727 (3)153
C21—H21···CL110.952.673.590 (3)164
C23—H23···CL11v0.952.893.399 (3)115
C23—H23···CL12vi0.952.853.751 (3)158
C24—H24···CL11v0.952.853.384 (3)117
C24—H24···CL21v0.952.823.697 (3)155
C25—H25A···CL120.982.803.746 (3)165
C26—H26A···CL21v0.992.843.656 (3)141
C26—H26A···CL22vii0.992.853.736 (3)149
C26—H26B···CL220.992.813.592 (3)137
Symmetry codes: (iii) x, y1, z; (iv) x+1, y, z; (v) x1, y, z; (vi) x, y+1, z; (vii) x, y+1, z+1.
 

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