Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Reaction of di-2-pyridyl ketone N4-ethyl­thio­semicarbazone with SnPh2Cl2 resulted in the formation of the title complex salt, namely 2-[(ethyl­amino­thio­yl­hydrazono)(2-pyridyl)­methyl]­pyridinium tetra­chloro­di­phenyl­stannate(IV), (C14H16N5S)2[SnCl4(C6H5)2]. The Sn atom is not coordin­ated directly by the nitro­gen base, but one of the pyridines of dipyridylketone is protonated, forming the cation. The Sn atom of the anion lies on an inversion center; thus, the two phenyl groups are trans to each other, with an Sn—C distance of 2.1424 (14) Å. The Sn—Cl distances are 2.5541 (4) and 2.6066 (4) Å. The N—H groups form hydrogen bonds to Cl atoms of the anion and the cation contains an intramolecular N—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015508/lh6238sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015508/lh6238Isup2.hkl
Contains datablock I

CCDC reference: 248695

Key indicators

  • Single-crystal X-ray study
  • T = 102 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.066
  • Data-to-parameter ratio = 31.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.50 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - C1 .. 5.26 su
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 2 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

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2-[(ethylaminothioylhydrazono)(2-pyridyl)methyl]pyridinium tetrachlorodiphenylstannate(IV) top
Crystal data top
2C14H16N5S+·C12H10Cl4Sn2Z = 1
Mr = 987.45F(000) = 502
Triclinic, P1Dx = 1.537 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4878 (10) ÅCell parameters from 7524 reflections
b = 12.009 (2) Åθ = 2.5–33.7°
c = 13.585 (2) ŵ = 0.99 mm1
α = 110.872 (9)°T = 102 K
β = 102.803 (7)°Fragment, yellow
γ = 100.404 (7)°0.35 × 0.30 × 0.20 mm
V = 1066.9 (3) Å3
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
8420 independent reflections
Radiation source: fine-focus sealed tube7364 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scans with κ offsetsθmax = 33.7°, θmin = 2.8°
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor 1997)
h = 1111
Tmin = 0.696, Tmax = 0.820k = 1818
34148 measured reflectionsl = 2120
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.0222P)2 + 0.6943P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
8420 reflectionsΔρmax = 0.87 e Å3
270 parametersΔρmin = 0.82 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0072 (7)
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
Sn10.00000.50000.00000.01112 (4)
Cl10.25764 (5)0.42032 (3)0.08791 (3)0.01529 (6)
Cl20.23999 (5)0.60871 (3)0.07324 (3)0.01528 (6)
S10.52760 (5)0.16520 (3)0.35629 (3)0.01867 (7)
N10.66877 (17)0.63291 (11)0.23120 (10)0.0135 (2)
H1N0.689 (3)0.5640 (18)0.2019 (16)0.016*
N20.7484 (2)0.58289 (12)0.57396 (10)0.0186 (2)
N30.64295 (17)0.47978 (11)0.33260 (10)0.0136 (2)
N40.64409 (18)0.39372 (11)0.37465 (10)0.0150 (2)
H4N0.660 (3)0.4163 (18)0.4447 (17)0.018*
N50.5342 (2)0.24590 (12)0.19616 (11)0.0203 (2)
H5N0.556 (3)0.310 (2)0.1784 (17)0.024*
C10.08042 (19)0.66536 (13)0.14971 (11)0.0143 (2)
C20.1180 (2)0.65826 (15)0.25217 (11)0.0180 (3)
H20.11580.58050.25570.022*
C30.1587 (2)0.76431 (17)0.34945 (13)0.0246 (3)
H30.18580.75880.41900.030*
C40.1598 (2)0.87768 (17)0.34480 (14)0.0290 (4)
H40.18400.94950.41090.035*
C50.1254 (2)0.88641 (15)0.24325 (15)0.0263 (3)
H50.12880.96460.24020.032*
C60.0860 (2)0.78074 (14)0.14605 (13)0.0190 (3)
H60.06270.78710.07690.023*
C70.70636 (19)0.59739 (13)0.39836 (11)0.0132 (2)
C80.67596 (19)0.67788 (12)0.33909 (11)0.0124 (2)
C90.6409 (2)0.79181 (13)0.38432 (12)0.0164 (2)
H90.64490.82600.45980.020*
C100.6000 (2)0.85575 (14)0.31859 (13)0.0193 (3)
H100.57670.93420.34930.023*
C110.5930 (2)0.80512 (15)0.20838 (13)0.0198 (3)
H110.56460.84810.16290.024*
C120.6278 (2)0.69140 (14)0.16563 (12)0.0170 (3)
H120.62270.65490.09010.020*
C130.7985 (2)0.65333 (13)0.52051 (11)0.0142 (2)
C140.9350 (2)0.76891 (14)0.57500 (12)0.0172 (3)
H140.96780.81620.53520.021*
C151.0227 (2)0.81401 (15)0.68870 (12)0.0210 (3)
H151.11760.89200.72760.025*
C160.9692 (2)0.74321 (16)0.74418 (12)0.0239 (3)
H161.02540.77200.82190.029*
C170.8316 (3)0.62918 (15)0.68343 (12)0.0228 (3)
H170.79450.58130.72190.027*
C180.5668 (2)0.27008 (13)0.30260 (12)0.0150 (2)
C190.4663 (2)0.12212 (15)0.10593 (13)0.0237 (3)
H19A0.50290.06190.13490.028*
H19B0.52960.12160.04910.028*
C200.2530 (3)0.08137 (19)0.05264 (18)0.0375 (5)
H20A0.18960.07740.10760.056*
H20B0.21490.00100.00880.056*
H20C0.21580.14110.02450.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01193 (6)0.01205 (6)0.00996 (6)0.00373 (4)0.00358 (4)0.00497 (4)
Cl10.01471 (14)0.01932 (15)0.01437 (13)0.00740 (12)0.00393 (11)0.00890 (12)
Cl20.01641 (14)0.01547 (15)0.01631 (14)0.00384 (11)0.00793 (12)0.00784 (12)
S10.02202 (17)0.01413 (16)0.02352 (17)0.00539 (13)0.00830 (14)0.01101 (14)
N10.0148 (5)0.0131 (5)0.0128 (5)0.0044 (4)0.0042 (4)0.0056 (4)
N20.0280 (6)0.0169 (6)0.0135 (5)0.0088 (5)0.0080 (5)0.0072 (4)
N30.0165 (5)0.0115 (5)0.0144 (5)0.0041 (4)0.0064 (4)0.0062 (4)
N40.0211 (6)0.0115 (5)0.0128 (5)0.0037 (4)0.0055 (4)0.0058 (4)
N50.0306 (7)0.0118 (5)0.0158 (5)0.0042 (5)0.0060 (5)0.0041 (4)
C10.0120 (5)0.0150 (6)0.0149 (6)0.0038 (5)0.0037 (5)0.0052 (5)
C20.0158 (6)0.0215 (7)0.0128 (6)0.0038 (5)0.0033 (5)0.0045 (5)
C30.0175 (7)0.0329 (9)0.0134 (6)0.0034 (6)0.0035 (5)0.0009 (6)
C40.0199 (7)0.0245 (8)0.0242 (7)0.0016 (6)0.0049 (6)0.0071 (6)
C50.0206 (7)0.0139 (7)0.0350 (9)0.0036 (6)0.0060 (6)0.0018 (6)
C60.0168 (6)0.0148 (6)0.0228 (7)0.0035 (5)0.0044 (5)0.0063 (5)
C70.0155 (6)0.0133 (6)0.0122 (5)0.0043 (5)0.0053 (4)0.0061 (5)
C80.0129 (5)0.0119 (5)0.0126 (5)0.0036 (4)0.0044 (4)0.0052 (4)
C90.0180 (6)0.0140 (6)0.0175 (6)0.0054 (5)0.0062 (5)0.0060 (5)
C100.0201 (7)0.0142 (6)0.0259 (7)0.0068 (5)0.0074 (6)0.0099 (6)
C110.0203 (7)0.0199 (7)0.0230 (7)0.0069 (6)0.0052 (5)0.0135 (6)
C120.0164 (6)0.0198 (7)0.0164 (6)0.0047 (5)0.0045 (5)0.0098 (5)
C130.0164 (6)0.0138 (6)0.0127 (5)0.0059 (5)0.0048 (5)0.0048 (5)
C140.0156 (6)0.0181 (6)0.0150 (6)0.0044 (5)0.0045 (5)0.0041 (5)
C150.0172 (6)0.0224 (7)0.0159 (6)0.0061 (6)0.0013 (5)0.0016 (5)
C160.0285 (8)0.0287 (8)0.0125 (6)0.0160 (7)0.0031 (6)0.0044 (6)
C170.0362 (9)0.0230 (7)0.0146 (6)0.0153 (7)0.0096 (6)0.0093 (6)
C180.0164 (6)0.0128 (6)0.0174 (6)0.0052 (5)0.0060 (5)0.0070 (5)
C190.0288 (8)0.0156 (7)0.0198 (7)0.0049 (6)0.0060 (6)0.0014 (5)
C200.0285 (9)0.0270 (9)0.0375 (10)0.0065 (7)0.0003 (8)0.0019 (8)
Geometric parameters (Å, º) top
Sn1—C1i2.1424 (14)C5—C61.393 (2)
Sn1—C12.1424 (14)C5—H50.9500
Sn1—Cl1i2.5541 (4)C6—H60.9500
Sn1—Cl12.5541 (4)C7—C81.4789 (19)
Sn1—Cl2i2.6066 (4)C7—C131.4872 (19)
Sn1—Cl22.6066 (4)C8—C91.3857 (19)
S1—C181.6794 (15)C9—C101.390 (2)
N1—C121.3356 (18)C9—H90.9500
N1—C81.3541 (17)C10—C111.385 (2)
N1—H1N0.840 (19)C10—H100.9500
N2—C171.3356 (19)C11—C121.379 (2)
N2—C131.3518 (19)C11—H110.9500
N3—C71.2996 (18)C12—H120.9500
N3—N41.3476 (16)C13—C141.393 (2)
N4—C181.3786 (18)C14—C151.391 (2)
N4—H4N0.86 (2)C14—H140.9500
N5—C181.3243 (19)C15—C161.385 (2)
N5—C191.457 (2)C15—H150.9500
N5—H5N0.88 (2)C16—C171.388 (3)
C1—C21.394 (2)C16—H160.9500
C1—C61.398 (2)C17—H170.9500
C2—C31.394 (2)C19—C201.506 (3)
C2—H20.9500C19—H19A0.9900
C3—C41.384 (3)C19—H19B0.9900
C3—H30.9500C20—H20A0.9800
C4—C51.391 (3)C20—H20B0.9800
C4—H40.9500C20—H20C0.9800
C1i—Sn1—C1180.0C8—C7—C13120.26 (12)
C1i—Sn1—Cl1i90.82 (4)N1—C8—C9118.06 (12)
C1—Sn1—Cl1i89.18 (4)N1—C8—C7117.48 (11)
C1i—Sn1—Cl189.18 (4)C9—C8—C7124.29 (12)
C1—Sn1—Cl190.82 (4)C8—C9—C10119.60 (13)
Cl1i—Sn1—Cl1180.0C8—C9—H9120.2
C1i—Sn1—Cl2i90.56 (4)C10—C9—H9120.2
C1—Sn1—Cl2i89.44 (4)C11—C10—C9120.01 (14)
Cl1i—Sn1—Cl2i90.515 (15)C11—C10—H10120.0
Cl1—Sn1—Cl2i89.484 (15)C9—C10—H10120.0
C1i—Sn1—Cl289.44 (4)C12—C11—C10119.05 (14)
C1—Sn1—Cl290.56 (4)C12—C11—H11120.5
Cl1i—Sn1—Cl289.486 (15)C10—C11—H11120.5
Cl1—Sn1—Cl290.516 (15)N1—C12—C11119.50 (13)
Cl2i—Sn1—Cl2179.999 (1)N1—C12—H12120.2
C12—N1—C8123.76 (12)C11—C12—H12120.2
C12—N1—H1N116.4 (13)N2—C13—C14122.40 (13)
C8—N1—H1N119.8 (13)N2—C13—C7116.02 (12)
C17—N2—C13117.60 (14)C14—C13—C7121.51 (13)
C7—N3—N4120.13 (12)C15—C14—C13118.93 (14)
N3—N4—C18118.33 (12)C15—C14—H14120.5
N3—N4—H4N119.0 (13)C13—C14—H14120.5
C18—N4—H4N120.0 (13)C16—C15—C14118.87 (15)
C18—N5—C19125.27 (13)C16—C15—H15120.6
C18—N5—H5N117.5 (14)C14—C15—H15120.6
C19—N5—H5N117.2 (14)C15—C16—C17118.40 (14)
C2—C1—C6118.97 (13)C15—C16—H16120.8
C2—C1—Sn1120.23 (11)C17—C16—H16120.8
C6—C1—Sn1120.70 (11)N2—C17—C16123.77 (15)
C3—C2—C1120.59 (15)N2—C17—H17118.1
C3—C2—H2119.7C16—C17—H17118.1
C1—C2—H2119.7N5—C18—N4115.55 (13)
C4—C3—C2120.03 (16)N5—C18—S1126.28 (11)
C4—C3—H3120.0N4—C18—S1118.15 (11)
C2—C3—H3120.0N5—C19—C20112.51 (14)
C3—C4—C5119.95 (15)N5—C19—H19A109.1
C3—C4—H4120.0C20—C19—H19A109.1
C5—C4—H4120.0N5—C19—H19B109.1
C4—C5—C6120.09 (16)C20—C19—H19B109.1
C4—C5—H5120.0H19A—C19—H19B107.8
C6—C5—H5120.0C19—C20—H20A109.5
C5—C6—C1120.34 (15)C19—C20—H20B109.5
C5—C6—H6119.8H20A—C20—H20B109.5
C1—C6—H6119.8C19—C20—H20C109.5
N3—C7—C8112.66 (12)H20A—C20—H20C109.5
N3—C7—C13127.07 (12)H20B—C20—H20C109.5
C7—N3—N4—C18176.81 (13)C13—C7—C8—C931.7 (2)
Cl1i—Sn1—C1—C2136.51 (11)N1—C8—C9—C100.0 (2)
Cl1—Sn1—C1—C243.49 (11)C7—C8—C9—C10175.13 (14)
Cl2i—Sn1—C1—C245.99 (11)C8—C9—C10—C110.4 (2)
Cl2—Sn1—C1—C2134.01 (11)C9—C10—C11—C120.2 (2)
Cl1i—Sn1—C1—C640.00 (11)C8—N1—C12—C111.0 (2)
Cl1—Sn1—C1—C6140.00 (11)C10—C11—C12—N10.5 (2)
Cl2i—Sn1—C1—C6130.52 (11)C17—N2—C13—C141.6 (2)
Cl2—Sn1—C1—C649.48 (11)C17—N2—C13—C7178.59 (13)
C6—C1—C2—C30.6 (2)N3—C7—C13—N227.3 (2)
Sn1—C1—C2—C3175.98 (11)C8—C7—C13—N2151.78 (13)
C1—C2—C3—C40.8 (2)N3—C7—C13—C14149.66 (14)
C2—C3—C4—C51.8 (2)C8—C7—C13—C1431.21 (19)
C3—C4—C5—C61.4 (3)N2—C13—C14—C150.3 (2)
C4—C5—C6—C10.1 (2)C7—C13—C14—C15177.11 (13)
C2—C1—C6—C51.0 (2)C13—C14—C15—C160.9 (2)
Sn1—C1—C6—C5175.52 (11)C14—C15—C16—C170.8 (2)
N4—N3—C7—C8174.09 (12)C13—N2—C17—C161.8 (2)
N4—N3—C7—C135.1 (2)C15—C16—C17—N20.6 (2)
C12—N1—C8—C90.8 (2)C19—N5—C18—N4175.39 (14)
C12—N1—C8—C7174.71 (13)C19—N5—C18—S13.2 (2)
N3—C7—C8—N127.67 (17)N3—N4—C18—N513.49 (19)
C13—C7—C8—N1153.09 (12)N3—N4—C18—S1167.80 (10)
N3—C7—C8—C9147.51 (14)C18—N5—C19—C2095.9 (2)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl2ii0.840 (19)2.421 (19)3.2279 (13)161.4 (17)
N4—H4N···N20.86 (2)2.01 (2)2.6723 (18)133.0 (17)
N5—H5N···Cl2ii0.88 (2)2.60 (2)3.3103 (15)138.7 (17)
Symmetry code: (ii) x+1, y+1, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds