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In the crystal structure of the title compound, C8H7Cl2N3S, the Schiff base is approximately planar. An intra­molecular N—H...S hydrogen bond stabilizes the mol­ecular structure. The mol­ecules are linked by N—H...S and N—H...Cl hydrogen bonds, forming a chain along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036865/at2094sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036865/at2094Isup2.hkl
Contains datablock I

CCDC reference: 623962

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.027
  • wR factor = 0.072
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 5.64 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. CL1 .. 2.95 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

(E)-1-(2,4-Dichlorobenzylidene)thiosemicarbazide top
Crystal data top
C8H7Cl2N3SZ = 2
Mr = 248.13F(000) = 252
Triclinic, P1Dx = 1.611 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 7.8840 (12) ÅCell parameters from 1824 reflections
b = 8.1407 (13) Åθ = 2.6–27.8°
c = 8.3101 (14) ŵ = 0.80 mm1
α = 100.603 (8)°T = 113 K
β = 101.290 (8)°Block, colourless
γ = 93.550 (9)°0.22 × 0.18 × 0.16 mm
V = 511.44 (14) Å3
Data collection top
Rigaku Saturn
diffractometer
2411 independent reflections
Radiation source: rotating anode1860 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.032
Detector resolution: 7.31 pixels mm-1θmax = 27.8°, θmin = 2.6°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.844, Tmax = 0.883l = 1010
6307 measured reflections
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)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0392P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
2411 reflectionsΔρmax = 0.32 e Å3
141 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.058 (6)
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
Cl10.27717 (6)0.04297 (5)0.51954 (5)0.02956 (15)
Cl20.44450 (5)0.23381 (5)0.01707 (4)0.01858 (12)
S10.04947 (5)0.77161 (4)1.09708 (5)0.01505 (12)
N10.12433 (18)0.86165 (17)0.82603 (18)0.0185 (3)
N20.13221 (16)0.58437 (15)0.83655 (15)0.0132 (3)
N30.18089 (15)0.55800 (16)0.68523 (15)0.0143 (3)
C10.10287 (18)0.73955 (18)0.90792 (18)0.0129 (3)
C20.20699 (19)0.40743 (19)0.62849 (18)0.0139 (3)
H20.18910.32240.68960.017*
C30.26414 (18)0.36426 (18)0.47057 (18)0.0126 (3)
C40.30179 (19)0.20260 (18)0.40910 (18)0.0151 (3)
C50.35839 (18)0.16003 (18)0.26126 (18)0.0154 (3)
H50.38290.04860.22240.018*
C60.37824 (18)0.28415 (19)0.17159 (18)0.0140 (3)
C70.34232 (19)0.44700 (19)0.22689 (18)0.0152 (3)
H70.35650.53090.16350.018*
C80.28602 (18)0.48579 (18)0.37445 (18)0.0150 (3)
H80.26140.59740.41230.018*
H10.091 (2)0.957 (2)0.859 (2)0.030 (5)*
H30.145 (2)0.833 (2)0.732 (2)0.030 (6)*
H40.104 (2)0.504 (2)0.868 (2)0.027 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0584 (3)0.0157 (2)0.0238 (2)0.00910 (19)0.0236 (2)0.00963 (17)
Cl20.0195 (2)0.0245 (2)0.0142 (2)0.00306 (16)0.00847 (15)0.00480 (15)
S10.0213 (2)0.01092 (19)0.0143 (2)0.00307 (15)0.00673 (16)0.00227 (14)
N10.0276 (8)0.0126 (7)0.0205 (8)0.0064 (6)0.0129 (6)0.0068 (6)
N20.0179 (7)0.0110 (7)0.0125 (6)0.0011 (5)0.0065 (5)0.0035 (5)
N30.0133 (6)0.0173 (6)0.0126 (6)0.0008 (5)0.0047 (5)0.0021 (5)
C10.0085 (7)0.0132 (7)0.0155 (8)0.0012 (6)0.0001 (6)0.0023 (6)
C20.0145 (7)0.0148 (7)0.0127 (7)0.0014 (6)0.0026 (6)0.0036 (6)
C30.0100 (7)0.0157 (7)0.0118 (7)0.0005 (6)0.0017 (6)0.0026 (6)
C40.0172 (8)0.0150 (8)0.0146 (8)0.0012 (6)0.0035 (6)0.0069 (6)
C50.0165 (8)0.0144 (8)0.0152 (8)0.0027 (6)0.0042 (6)0.0018 (6)
C60.0097 (7)0.0221 (8)0.0102 (7)0.0005 (6)0.0023 (6)0.0038 (6)
C70.0152 (7)0.0172 (8)0.0146 (8)0.0006 (6)0.0034 (6)0.0064 (6)
C80.0151 (8)0.0138 (7)0.0161 (8)0.0028 (6)0.0026 (6)0.0035 (6)
Geometric parameters (Å, º) top
Cl1—C41.7453 (14)C2—H20.9500
Cl2—C61.7348 (15)C3—C41.393 (2)
S1—C11.6847 (15)C3—C81.404 (2)
N1—C11.3239 (19)C4—C51.381 (2)
N1—H10.846 (19)C5—C61.380 (2)
N1—H30.826 (18)C5—H50.9500
N2—C11.3474 (18)C6—C71.386 (2)
N2—N31.3691 (16)C7—C81.374 (2)
N2—H40.783 (17)C7—H70.9500
N3—C21.2742 (19)C8—H80.9500
C2—C31.4595 (19)
C1—N1—H1119.6 (13)C5—C4—C3122.90 (13)
C1—N1—H3116.1 (12)C5—C4—Cl1117.01 (11)
H1—N1—H3122.2 (16)C3—C4—Cl1120.09 (11)
C1—N2—N3120.08 (12)C6—C5—C4118.00 (14)
C1—N2—H4122.1 (14)C6—C5—H5121.0
N3—N2—H4116.6 (14)C4—C5—H5121.0
C2—N3—N2115.49 (12)C5—C6—C7121.47 (13)
N1—C1—N2117.12 (13)C5—C6—Cl2119.17 (12)
N1—C1—S1123.20 (12)C7—C6—Cl2119.34 (11)
N2—C1—S1119.63 (11)C8—C7—C6119.28 (14)
N3—C2—C3120.68 (13)C8—C7—H7120.4
N3—C2—H2119.7C6—C7—H7120.4
C3—C2—H2119.7C7—C8—C3121.49 (14)
C4—C3—C8116.86 (13)C7—C8—H8119.3
C4—C3—C2122.09 (13)C3—C8—H8119.3
C8—C3—C2121.04 (13)
C1—N2—N3—C2179.46 (13)C3—C4—C5—C60.1 (2)
N3—N2—C1—N10.4 (2)Cl1—C4—C5—C6179.79 (11)
N3—N2—C1—S1177.99 (10)C4—C5—C6—C70.2 (2)
N2—N3—C2—C3178.28 (12)C4—C5—C6—Cl2178.58 (11)
N3—C2—C3—C4176.88 (14)C5—C6—C7—C80.1 (2)
N3—C2—C3—C82.2 (2)Cl2—C6—C7—C8178.52 (11)
C8—C3—C4—C50.1 (2)C6—C7—C8—C30.0 (2)
C2—C3—C4—C5179.04 (13)C4—C3—C8—C70.1 (2)
C8—C3—C4—Cl1179.63 (11)C2—C3—C8—C7178.99 (13)
C2—C3—C4—Cl11.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.846 (19)2.534 (19)3.3685 (15)169.0 (16)
N1—H3···Cl1ii0.826 (18)2.955 (17)3.5331 (15)128.9 (15)
N2—H4···S1iii0.783 (17)2.574 (17)3.3372 (14)165.1 (17)
Symmetry codes: (i) x, y+2, z+2; (ii) x, y+1, z; (iii) x, y+1, z+2.
 

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