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The title compound was prepared by the reaction of [butane-2,3-dione bis­(4-methyl­thio­semicarbazonato)]zinc(II) with pyridine. The ZnII atom is five-coordinate in a pseudo-square-pyramidal geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015019234/pj2023sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015019234/pj2023Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989015019234/pj2023sup3.pdf
Supplementary material

CCDC reference: 1430734

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.074
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level C PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.090 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 16 Report
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 65 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: (CrysAlis PRO; Agilent, 2014); cell refinement: (CrysAlis PRO; Agilent, 2014); data reduction: (CrysAlis PRO; Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

[Butane-2,3-dione bis(4-methylthiosemicarbazonato)-κ4S,N1,N1',S'](pyridine-κN)zinc(II) top
Crystal data top
[Zn(C8H14N6S2)(C5H5N)]F(000) = 832
Mr = 402.84Dx = 1.535 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 10.1466 (2) ÅCell parameters from 6492 reflections
b = 13.9076 (3) Åθ = 4.8–73.0°
c = 12.7775 (3) ŵ = 4.27 mm1
β = 104.756 (2)°T = 150 K
V = 1743.64 (7) Å3Needle, clear yellow
Z = 40.26 × 0.04 × 0.02 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Atlas detector
3445 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source3020 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.041
Detector resolution: 5.2031 pixels mm-1θmax = 73.6°, θmin = 4.8°
ω scansh = 712
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1617
Tmin = 0.775, Tmax = 1.000l = 1515
12050 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.032P)2 + 1.1359P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3445 reflectionsΔρmax = 0.36 e Å3
212 parametersΔρmin = 0.42 e Å3
0 restraints
Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Zn10.30020 (3)0.73515 (2)0.47000 (2)0.01926 (9)
S10.44685 (5)0.79566 (4)0.36852 (4)0.02284 (12)
S20.14259 (6)0.85069 (4)0.50133 (4)0.02449 (13)
N10.68465 (19)0.71828 (14)0.37359 (15)0.0248 (4)
H10.68130.76000.32330.030*
N20.59011 (19)0.65189 (13)0.50031 (15)0.0235 (4)
N30.47831 (18)0.65526 (13)0.54215 (14)0.0203 (4)
N40.26884 (18)0.68075 (13)0.61711 (14)0.0213 (4)
N50.15519 (18)0.70523 (13)0.65027 (14)0.0215 (4)
N60.02309 (19)0.80647 (14)0.62535 (15)0.0257 (4)
H60.04110.77580.67850.031*
N70.17142 (18)0.64416 (13)0.35929 (14)0.0213 (4)
C10.8028 (2)0.65595 (18)0.4039 (2)0.0301 (5)
H1A0.86620.67250.36240.045*
H1B0.77480.59030.38980.045*
H1C0.84570.66380.47960.045*
C20.5800 (2)0.71402 (15)0.42040 (17)0.0214 (4)
C30.4771 (2)0.60479 (15)0.62697 (16)0.0211 (4)
C40.5913 (3)0.54130 (19)0.6841 (2)0.0344 (6)
H4A0.56470.47520.67120.052*
H4B0.61270.55420.76040.052*
H4C0.67000.55370.65750.052*
C50.3557 (2)0.61910 (15)0.66955 (16)0.0200 (4)
C60.3438 (2)0.56830 (17)0.76987 (17)0.0251 (4)
H6A0.40860.59470.83140.038*
H6B0.36180.50100.76390.038*
H6C0.25330.57660.77880.038*
C70.0907 (2)0.78126 (15)0.59668 (17)0.0215 (4)
C80.1183 (2)0.88087 (17)0.57441 (18)0.0269 (5)
H8A0.16950.85910.50460.040*
H8B0.06890.93810.56620.040*
H8C0.17940.89460.61880.040*
C90.1317 (2)0.67116 (17)0.25522 (18)0.0264 (5)
H90.16500.72870.23500.032*
C100.0434 (2)0.61722 (18)0.17651 (19)0.0313 (5)
H100.01770.63810.10500.038*
C110.0057 (2)0.53150 (17)0.2068 (2)0.0301 (5)
H110.06520.49370.15580.036*
C120.0346 (2)0.50294 (17)0.3136 (2)0.0301 (5)
H120.00300.44550.33560.036*
C130.1226 (2)0.56104 (16)0.38725 (18)0.0247 (4)
H130.14920.54170.45920.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01595 (15)0.02595 (15)0.01686 (14)0.00116 (10)0.00599 (10)0.00201 (10)
S10.0201 (3)0.0283 (3)0.0226 (2)0.00170 (19)0.0101 (2)0.00528 (19)
S20.0234 (3)0.0268 (3)0.0264 (3)0.0057 (2)0.0122 (2)0.0057 (2)
N10.0194 (9)0.0345 (10)0.0227 (9)0.0000 (7)0.0097 (7)0.0049 (7)
N20.0193 (9)0.0316 (10)0.0219 (8)0.0020 (7)0.0095 (7)0.0024 (7)
N30.0158 (9)0.0268 (9)0.0191 (8)0.0023 (7)0.0060 (7)0.0020 (7)
N40.0202 (9)0.0270 (9)0.0186 (8)0.0011 (7)0.0081 (7)0.0002 (7)
N50.0149 (9)0.0318 (9)0.0201 (8)0.0022 (7)0.0088 (7)0.0010 (7)
N60.0182 (9)0.0365 (10)0.0246 (9)0.0064 (8)0.0098 (7)0.0051 (8)
N70.0159 (9)0.0259 (9)0.0221 (8)0.0001 (7)0.0050 (7)0.0005 (7)
C10.0169 (11)0.0405 (13)0.0358 (12)0.0037 (9)0.0118 (9)0.0010 (10)
C20.0176 (10)0.0268 (10)0.0209 (10)0.0029 (8)0.0069 (8)0.0028 (8)
C30.0178 (10)0.0270 (10)0.0192 (9)0.0017 (8)0.0060 (8)0.0019 (8)
C40.0292 (13)0.0448 (14)0.0331 (12)0.0165 (11)0.0149 (10)0.0157 (11)
C50.0179 (10)0.0257 (10)0.0165 (9)0.0013 (8)0.0047 (8)0.0002 (8)
C60.0185 (11)0.0355 (12)0.0210 (10)0.0003 (9)0.0047 (8)0.0051 (9)
C70.0183 (11)0.0295 (11)0.0171 (9)0.0006 (8)0.0055 (8)0.0036 (8)
C80.0209 (11)0.0346 (12)0.0263 (11)0.0062 (9)0.0077 (9)0.0014 (9)
C90.0230 (12)0.0300 (11)0.0247 (11)0.0010 (9)0.0034 (9)0.0025 (9)
C100.0255 (12)0.0408 (13)0.0242 (11)0.0011 (10)0.0004 (9)0.0004 (9)
C110.0203 (11)0.0334 (12)0.0346 (12)0.0013 (9)0.0032 (9)0.0096 (10)
C120.0240 (12)0.0258 (11)0.0410 (13)0.0018 (9)0.0094 (10)0.0021 (10)
C130.0197 (11)0.0274 (11)0.0280 (11)0.0017 (9)0.0080 (8)0.0037 (9)
Geometric parameters (Å, º) top
Zn1—S12.3635 (6)C1—H1C0.9600
Zn1—S22.3718 (6)C3—C41.491 (3)
Zn1—N32.1218 (18)C3—C51.482 (3)
Zn1—N42.1241 (17)C4—H4A0.9600
Zn1—N72.0900 (18)C4—H4B0.9600
S1—C21.760 (2)C4—H4C0.9600
S2—C71.738 (2)C5—C61.495 (3)
N1—H10.8600C6—H6A0.9600
N1—C11.450 (3)C6—H6B0.9600
N1—C21.347 (3)C6—H6C0.9600
N2—N31.372 (3)C8—H8A0.9600
N2—C21.321 (3)C8—H8B0.9600
N3—C31.294 (3)C8—H8C0.9600
N4—N51.369 (2)C9—H90.9300
N4—C51.288 (3)C9—C101.385 (3)
N5—C71.337 (3)C10—H100.9300
N6—H60.8600C10—C111.385 (4)
N6—C71.344 (3)C11—H110.9300
N6—C81.452 (3)C11—C121.379 (4)
N7—C91.341 (3)C12—H120.9300
N7—C131.341 (3)C12—C131.382 (3)
C1—H1A0.9600C13—H130.9300
C1—H1B0.9600
S1—Zn1—S2113.40 (2)C5—C3—C4120.98 (18)
N3—Zn1—S180.75 (5)C3—C4—H4A109.5
N3—Zn1—S2144.85 (5)C3—C4—H4B109.5
N3—Zn1—N474.45 (7)C3—C4—H4C109.5
N4—Zn1—S1150.39 (5)H4A—C4—H4B109.5
N4—Zn1—S280.36 (5)H4A—C4—H4C109.5
N7—Zn1—S1102.52 (5)H4B—C4—H4C109.5
N7—Zn1—S2101.09 (5)N4—C5—C3114.89 (18)
N7—Zn1—N3107.07 (7)N4—C5—C6124.51 (19)
N7—Zn1—N4100.05 (7)C3—C5—C6120.51 (18)
C2—S1—Zn195.38 (7)C5—C6—H6A109.5
C7—S2—Zn194.57 (7)C5—C6—H6B109.5
C1—N1—H1118.4C5—C6—H6C109.5
C2—N1—H1118.4H6A—C6—H6B109.5
C2—N1—C1123.16 (19)H6A—C6—H6C109.5
C2—N2—N3111.67 (18)H6B—C6—H6C109.5
N2—N3—Zn1123.07 (13)N5—C7—S2127.03 (16)
C3—N3—Zn1117.35 (14)N5—C7—N6114.16 (19)
C3—N3—N2119.53 (18)N6—C7—S2118.75 (17)
N5—N4—Zn1120.87 (13)N6—C8—H8A109.5
C5—N4—Zn1117.43 (14)N6—C8—H8B109.5
C5—N4—N5121.53 (18)N6—C8—H8C109.5
C7—N5—N4112.29 (17)H8A—C8—H8B109.5
C7—N6—H6117.1H8A—C8—H8C109.5
C7—N6—C8125.71 (19)H8B—C8—H8C109.5
C8—N6—H6117.1N7—C9—H9118.5
C9—N7—Zn1118.66 (15)N7—C9—C10122.9 (2)
C13—N7—Zn1123.45 (15)C10—C9—H9118.5
C13—N7—C9117.86 (19)C9—C10—H10120.8
N1—C1—H1A109.5C11—C10—C9118.4 (2)
N1—C1—H1B109.5C11—C10—H10120.8
N1—C1—H1C109.5C10—C11—H11120.4
H1A—C1—H1B109.5C12—C11—C10119.1 (2)
H1A—C1—H1C109.5C12—C11—H11120.4
H1B—C1—H1C109.5C11—C12—H12120.6
N1—C2—S1114.89 (16)C11—C12—C13118.9 (2)
N2—C2—S1127.89 (17)C13—C12—H12120.6
N2—C2—N1117.2 (2)N7—C13—C12122.8 (2)
N3—C3—C4124.0 (2)N7—C13—H13118.6
N3—C3—C5114.89 (18)C12—C13—H13118.6
Zn1—S1—C2—N1173.89 (15)N4—N5—C7—N6178.74 (18)
Zn1—S1—C2—N27.9 (2)N5—N4—C5—C3176.54 (18)
Zn1—S2—C7—N517.1 (2)N5—N4—C5—C60.1 (3)
Zn1—S2—C7—N6165.88 (16)N7—C9—C10—C110.1 (4)
Zn1—N3—C3—C4177.10 (18)C1—N1—C2—S1179.04 (17)
Zn1—N3—C3—C56.8 (2)C1—N1—C2—N22.6 (3)
Zn1—N4—N5—C715.4 (2)C2—N2—N3—Zn18.8 (2)
Zn1—N4—C5—C38.2 (2)C2—N2—N3—C3174.17 (19)
Zn1—N4—C5—C6175.37 (16)C4—C3—C5—N4175.3 (2)
Zn1—N7—C9—C10178.02 (18)C4—C3—C5—C61.3 (3)
Zn1—N7—C13—C12178.17 (17)C5—N4—N5—C7169.43 (19)
N2—N3—C3—C40.1 (3)C8—N6—C7—S27.9 (3)
N2—N3—C3—C5175.95 (18)C8—N6—C7—N5174.7 (2)
N3—N2—C2—S11.0 (3)C9—N7—C13—C120.2 (3)
N3—N2—C2—N1179.17 (18)C9—C10—C11—C120.0 (4)
N3—C3—C5—N40.9 (3)C10—C11—C12—C130.2 (3)
N3—C3—C5—C6177.50 (19)C11—C12—C13—N70.4 (3)
N4—N5—C7—S24.1 (3)C13—N7—C9—C100.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N5i0.862.212.988 (3)150
N6—H6···S1ii0.862.653.500 (2)167
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (ii) x3/2, y+1/2, z1/2.
 

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