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Reaction of indium(III) chloride with (E)-1-[1-(2-pyrid­yl)ethyl­idene]thio­semicarbazide afforded the title complex, [In(C8H9N4S)Cl2(C2H5OH)]. The ligand is in the enol form coordinating to the InIII atom through one S atom and two N atoms. The InIII atom is further coordinated by two Cl atoms and an ethanol mol­ecule to complete a distorted octa­hedral coordination geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006290/hy2043sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006290/hy2043Isup2.hkl
Contains datablock I

CCDC reference: 640372

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.029
  • wR factor = 0.070
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.02 Ratio
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Dichloro(ethanol-κO){(E)-1-[1-(2-pyridyl)ethylidene]thiosemicarbazonato- κ3N,N',S}indium(III) top
Crystal data top
[In(C8H9N4S)Cl2(C2H6O)]F(000) = 840
Mr = 425.04Dx = 1.851 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4444 reflections
a = 7.1651 (12) Åθ = 2.6–28.1°
b = 13.331 (2) ŵ = 2.03 mm1
c = 16.269 (3) ÅT = 298 K
β = 101.012 (2)°Plate, yellow
V = 1525.3 (4) Å30.49 × 0.37 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2832 independent reflections
Radiation source: fine-focus sealed tube2555 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 86
Tmin = 0.436, Tmax = 0.871k = 1616
7787 measured reflectionsl = 1719
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0298P)2 + 0.5409P]
where P = (Fo2 + 2Fc2)/3
2832 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.57 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
In10.41828 (3)0.213470 (16)0.199943 (12)0.02607 (10)
N10.3136 (4)0.08807 (19)0.11022 (15)0.0298 (6)
N20.4097 (3)0.27106 (17)0.06922 (15)0.0238 (5)
N30.4547 (4)0.36871 (18)0.05459 (15)0.0273 (6)
N40.5590 (4)0.51670 (19)0.11290 (16)0.0397 (7)
H4A0.55590.53960.06320.048*
H4B0.59500.55480.15570.048*
C10.2727 (5)0.0035 (2)0.1341 (2)0.0386 (8)
H10.27670.01550.19070.046*
C20.2246 (5)0.0812 (3)0.0781 (2)0.0420 (8)
H20.19720.14460.09640.050*
C30.2183 (5)0.0623 (3)0.0049 (2)0.0396 (8)
H30.18640.11330.04410.048*
C40.2593 (5)0.0325 (2)0.0305 (2)0.0330 (7)
H40.25370.04590.08700.040*
C50.3087 (4)0.1076 (2)0.02832 (18)0.0261 (7)
C60.3595 (4)0.2112 (2)0.00661 (19)0.0274 (7)
C70.3501 (6)0.2428 (3)0.0818 (2)0.0444 (9)
H7A0.25030.29120.09700.067*
H7B0.32480.18540.11790.067*
H7C0.46930.27210.08760.067*
C80.5083 (4)0.4226 (2)0.12352 (18)0.0270 (7)
C90.0112 (6)0.3574 (3)0.1402 (3)0.0558 (11)
H9A0.10680.40950.15310.067*
H9B0.08960.37220.17060.067*
C100.0663 (7)0.3582 (4)0.0507 (3)0.0785 (15)
H10A0.03250.34230.02050.118*
H10B0.11640.42360.03450.118*
H10C0.16610.30940.03820.118*
H1A0.01530.22830.18460.094*
Cl10.74400 (12)0.13897 (6)0.21217 (5)0.0371 (2)
Cl20.33949 (15)0.14450 (7)0.32404 (5)0.0484 (2)
O10.0953 (4)0.2618 (2)0.16787 (18)0.0533 (7)
S10.52113 (12)0.38835 (6)0.22825 (5)0.0329 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
In10.03058 (15)0.02651 (14)0.02118 (14)0.00244 (8)0.00506 (9)0.00242 (8)
N10.0340 (15)0.0265 (14)0.0281 (14)0.0062 (11)0.0040 (11)0.0012 (11)
N20.0249 (14)0.0207 (13)0.0259 (13)0.0022 (10)0.0050 (10)0.0010 (10)
N30.0337 (15)0.0251 (13)0.0224 (13)0.0034 (11)0.0039 (10)0.0029 (10)
N40.067 (2)0.0263 (15)0.0264 (15)0.0100 (14)0.0104 (13)0.0018 (11)
C10.047 (2)0.0320 (18)0.0366 (19)0.0081 (15)0.0065 (15)0.0057 (14)
C20.046 (2)0.0288 (18)0.053 (2)0.0079 (16)0.0149 (17)0.0031 (16)
C30.043 (2)0.0326 (18)0.044 (2)0.0063 (15)0.0093 (16)0.0110 (15)
C40.0355 (19)0.0332 (18)0.0298 (17)0.0034 (14)0.0050 (13)0.0026 (13)
C50.0239 (16)0.0267 (16)0.0273 (16)0.0002 (12)0.0036 (12)0.0016 (12)
C60.0302 (18)0.0258 (16)0.0255 (16)0.0022 (12)0.0038 (13)0.0027 (12)
C70.072 (3)0.0349 (19)0.0247 (18)0.0075 (18)0.0053 (16)0.0002 (15)
C80.0290 (17)0.0256 (16)0.0269 (16)0.0005 (12)0.0067 (12)0.0021 (12)
C90.045 (2)0.060 (3)0.063 (3)0.015 (2)0.0123 (19)0.003 (2)
C100.058 (3)0.114 (4)0.065 (3)0.029 (3)0.013 (2)0.016 (3)
Cl10.0347 (5)0.0416 (5)0.0340 (4)0.0070 (3)0.0039 (3)0.0041 (3)
Cl20.0652 (6)0.0519 (6)0.0320 (5)0.0089 (5)0.0193 (4)0.0090 (4)
O10.0329 (15)0.0562 (17)0.074 (2)0.0075 (12)0.0181 (13)0.0275 (15)
S10.0472 (5)0.0281 (4)0.0233 (4)0.0047 (3)0.0065 (3)0.0011 (3)
Geometric parameters (Å, º) top
In1—N22.251 (2)C3—C41.380 (5)
In1—N12.252 (2)C3—H30.9300
In1—O12.363 (2)C4—C51.383 (4)
In1—Cl22.3823 (9)C4—H40.9300
In1—S12.4617 (9)C5—C61.487 (4)
In1—Cl12.5091 (9)C6—C71.488 (4)
N1—C11.330 (4)C7—H7A0.9600
N1—C51.351 (4)C7—H7B0.9600
N2—C61.290 (4)C7—H7C0.9600
N2—N31.373 (3)C8—S11.749 (3)
N3—C81.326 (4)C9—O11.444 (5)
N4—C81.326 (4)C9—C101.457 (5)
N4—H4A0.8600C9—H9A0.9700
N4—H4B0.8600C9—H9B0.9700
C1—C21.379 (5)C10—H10A0.9600
C1—H10.9300C10—H10B0.9600
C2—C31.366 (5)C10—H10C0.9600
C2—H20.9300O1—H1A0.814
N2—In1—N172.24 (9)C3—C4—C5119.7 (3)
N2—In1—O181.34 (9)C3—C4—H4120.2
N1—In1—O182.44 (10)C5—C4—H4120.2
N2—In1—Cl2164.63 (7)N1—C5—C4119.9 (3)
N1—In1—Cl299.17 (7)N1—C5—C6116.8 (3)
O1—In1—Cl284.94 (7)C4—C5—C6123.3 (3)
N2—In1—S178.87 (6)N2—C6—C5115.5 (3)
N1—In1—S1151.06 (7)N2—C6—C7122.8 (3)
O1—In1—S191.65 (8)C5—C6—C7121.6 (3)
Cl2—In1—S1108.54 (3)C6—C7—H7A109.5
N2—In1—Cl193.84 (7)C6—C7—H7B109.5
N1—In1—Cl186.97 (7)H7A—C7—H7B109.5
O1—In1—Cl1169.27 (8)C6—C7—H7C109.5
Cl2—In1—Cl198.48 (3)H7A—C7—H7C109.5
S1—In1—Cl196.85 (3)H7B—C7—H7C109.5
C1—N1—C5119.9 (3)N3—C8—N4116.4 (3)
C1—N1—In1123.8 (2)N3—C8—S1129.4 (2)
C5—N1—In1116.04 (19)N4—C8—S1114.2 (2)
C6—N2—N3119.3 (2)O1—C9—C10112.0 (4)
C6—N2—In1119.22 (19)O1—C9—H9A109.2
N3—N2—In1121.50 (18)C10—C9—H9A109.2
C8—N3—N2114.0 (2)O1—C9—H9B109.2
C8—N4—H4A120.0C10—C9—H9B109.2
C8—N4—H4B120.0H9A—C9—H9B107.9
H4A—N4—H4B120.0C9—C10—H10A109.5
N1—C1—C2122.5 (3)C9—C10—H10B109.5
N1—C1—H1118.7H10A—C10—H10B109.5
C2—C1—H1118.7C9—C10—H10C109.5
C3—C2—C1118.1 (3)H10A—C10—H10C109.5
C3—C2—H2120.9H10B—C10—H10C109.5
C1—C2—H2120.9C9—O1—In1130.0 (2)
C2—C3—C4119.9 (3)C9—O1—H1A108.0
C2—C3—H3120.1In1—O1—H1A120.0
C4—C3—H3120.1C8—S1—In196.15 (10)
N2—In1—N1—C1177.9 (3)In1—N1—C5—C4175.4 (2)
O1—In1—N1—C198.8 (3)C1—N1—C5—C6178.9 (3)
Cl2—In1—N1—C115.3 (3)In1—N1—C5—C64.2 (3)
S1—In1—N1—C1178.5 (2)C3—C4—C5—N11.0 (5)
Cl1—In1—N1—C182.8 (3)C3—C4—C5—C6178.5 (3)
N2—In1—N1—C53.3 (2)N3—N2—C6—C5178.5 (3)
O1—In1—N1—C586.6 (2)In1—N2—C6—C50.8 (4)
Cl2—In1—N1—C5170.2 (2)N3—N2—C6—C70.8 (5)
S1—In1—N1—C57.0 (3)In1—N2—C6—C7179.9 (3)
Cl1—In1—N1—C591.7 (2)N1—C5—C6—N22.3 (4)
N1—In1—N2—C62.2 (2)C4—C5—C6—N2177.3 (3)
O1—In1—N2—C687.0 (2)N1—C5—C6—C7177.0 (3)
Cl2—In1—N2—C660.0 (4)C4—C5—C6—C73.4 (5)
S1—In1—N2—C6179.6 (2)N2—N3—C8—N4178.0 (3)
Cl1—In1—N2—C683.4 (2)N2—N3—C8—S12.5 (4)
N1—In1—N2—N3177.1 (2)C10—C9—O1—In1102.4 (4)
O1—In1—N2—N392.3 (2)N2—In1—O1—C955.2 (3)
Cl2—In1—N2—N3119.3 (3)N1—In1—O1—C9128.2 (3)
S1—In1—N2—N31.1 (2)Cl2—In1—O1—C9131.8 (3)
Cl1—In1—N2—N397.3 (2)S1—In1—O1—C923.3 (3)
C6—N2—N3—C8178.5 (3)Cl1—In1—O1—C9119.1 (4)
In1—N2—N3—C82.2 (3)N3—C8—S1—In11.5 (3)
C5—N1—C1—C20.1 (5)N4—C8—S1—In1179.0 (2)
In1—N1—C1—C2174.3 (3)N2—In1—S1—C80.11 (12)
N1—C1—C2—C30.3 (6)N1—In1—S1—C83.67 (19)
C1—C2—C3—C40.1 (5)O1—In1—S1—C880.95 (13)
C2—C3—C4—C50.7 (5)Cl2—In1—S1—C8166.16 (11)
C1—N1—C5—C40.6 (5)Cl1—In1—S1—C892.48 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···Cl1i0.812.393.198 (3)170
N4—H4B···Cl1ii0.862.503.349 (3)168
N4—H4A···N3iii0.862.263.109 (4)168
Symmetry codes: (i) x1, y, z; (ii) x+3/2, y+1/2, z+1/2; (iii) x+1, y+1, z.
 

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