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ISSN: 2056-9890

1-(4-Chloro­benzyl­­idene)-4-ethyl­thio­semicarbazide

aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: liyufeng8111@163.com

(Received 11 November 2010; accepted 16 November 2010; online 20 November 2010)

In the title compound, C10H12ClN3S, the dihedral angle between the benzene ring and the thio­urea unit is 2.35 (19)°. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R22(8) loops.

Related literature

For related structures, see: Li & Jian (2010[Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399.]); Li & Meng (2010[Li, Y.-F. & Meng, F.-Y. (2010). Acta Cryst. E66, o2685.]).

[Scheme 1]

Experimental

Crystal data
  • C10H12ClN3S

  • Mr = 241.75

  • Monoclinic, P 21 /c

  • a = 4.6769 (10) Å

  • b = 26.727 (6) Å

  • c = 9.791 (3) Å

  • β = 102.59 (3)°

  • V = 1194.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.47 mm−1

  • T = 293 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 11437 measured reflections

  • 2723 independent reflections

  • 1388 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.272

  • S = 1.09

  • 2723 reflections

  • 136 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯S1i 0.86 2.59 3.383 (4) 154
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

For related structures, see: Li & Jian (2010); Li & Meng (2010).

Experimental top

A mixture of 4-ethylthiosemicarbazide (0.1 mol) and 4-chlorobenzaldehyde (0.1 mol) was stirred in refluxing ethanol (20 mL) for 2 h to afford the title compound (0.089 mol, yield 89%). Colourless bars were obtained by recrystallization from ethanol at room temperature.

Refinement top

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances=0.97 Å, and with Uiso=1.2–1.5Ueq.

Structure description top

For related structures, see: Li & Jian (2010); Li & Meng (2010).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids.
1-(4-Chlorobenzylidene)-4-ethylthiosemicarbazide top
Crystal data top
C10H12ClN3SF(000) = 504
Mr = 241.75Dx = 1.344 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2723 reflections
a = 4.6769 (10) Åθ = 3.1–27.5°
b = 26.727 (6) ŵ = 0.47 mm1
c = 9.791 (3) ÅT = 293 K
β = 102.59 (3)°Bar, colorless
V = 1194.4 (5) Å30.22 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
1388 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
phi and ω scansh = 65
11437 measured reflectionsk = 3434
2723 independent reflectionsl = 1212
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.272H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1156P)2 + 1.1747P]
where P = (Fo2 + 2Fc2)/3
2723 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C10H12ClN3SV = 1194.4 (5) Å3
Mr = 241.75Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.6769 (10) ŵ = 0.47 mm1
b = 26.727 (6) ÅT = 293 K
c = 9.791 (3) Å0.22 × 0.20 × 0.18 mm
β = 102.59 (3)°
Data collection top
Bruker SMART CCD
diffractometer
1388 reflections with I > 2σ(I)
11437 measured reflectionsRint = 0.066
2723 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.272H-atom parameters constrained
S = 1.09Δρmax = 0.33 e Å3
2723 reflectionsΔρmin = 0.34 e Å3
136 parameters
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
S11.2104 (3)0.01352 (5)0.72223 (14)0.0738 (5)
Cl10.3450 (4)0.27875 (6)0.46099 (18)0.1022 (6)
N20.7928 (8)0.04912 (15)0.6097 (4)0.0637 (10)
H2A0.76950.03110.53540.076*
N30.6207 (8)0.09071 (14)0.6128 (4)0.0616 (10)
C50.2251 (9)0.14199 (17)0.4970 (5)0.0576 (11)
C40.4166 (10)0.09865 (18)0.5041 (5)0.0622 (11)
H4A0.39070.07650.42910.075*
N11.0195 (10)0.06662 (17)0.8346 (4)0.0789 (13)
H1A0.89850.09120.82600.095*
C100.0157 (10)0.15053 (19)0.3771 (5)0.0664 (12)
H10A0.00660.12810.30280.080*
C60.2528 (11)0.1751 (2)0.6072 (5)0.0723 (13)
H6A0.39330.16950.68890.087*
C90.1627 (11)0.1925 (2)0.3665 (5)0.0709 (13)
H9A0.30450.19830.28530.085*
C30.9998 (10)0.03689 (17)0.7250 (5)0.0602 (11)
C80.1287 (11)0.22552 (19)0.4764 (5)0.0679 (12)
C70.0731 (14)0.2164 (2)0.5967 (6)0.0836 (16)
H7A0.08980.23820.67210.100*
C21.2242 (16)0.0617 (2)0.9669 (6)0.096 (2)
H2B1.14460.03831.02470.116*
H2C1.40450.04750.95060.116*
C11.290 (2)0.1061 (3)1.0404 (9)0.130 (3)
H1B1.42870.09971.12640.196*
H1C1.11420.11991.06060.196*
H1D1.37230.12940.98510.196*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0781 (9)0.0700 (8)0.0700 (8)0.0180 (6)0.0089 (6)0.0022 (6)
Cl10.1142 (13)0.0852 (11)0.1023 (12)0.0396 (9)0.0129 (9)0.0139 (8)
N20.060 (2)0.069 (2)0.061 (2)0.0125 (19)0.0087 (17)0.0022 (18)
N30.060 (2)0.062 (2)0.063 (2)0.0073 (19)0.0145 (18)0.0012 (17)
C50.054 (2)0.062 (3)0.055 (2)0.002 (2)0.0104 (19)0.0026 (19)
C40.057 (3)0.069 (3)0.059 (3)0.008 (2)0.010 (2)0.001 (2)
N10.087 (3)0.079 (3)0.063 (3)0.025 (2)0.000 (2)0.008 (2)
C100.063 (3)0.070 (3)0.062 (3)0.002 (2)0.006 (2)0.001 (2)
C60.072 (3)0.077 (3)0.060 (3)0.014 (3)0.003 (2)0.004 (2)
C90.066 (3)0.077 (3)0.064 (3)0.009 (3)0.001 (2)0.013 (2)
C30.057 (2)0.063 (3)0.062 (3)0.006 (2)0.013 (2)0.005 (2)
C80.068 (3)0.067 (3)0.067 (3)0.011 (2)0.011 (2)0.012 (2)
C70.098 (4)0.079 (4)0.068 (3)0.025 (3)0.005 (3)0.011 (3)
C20.111 (5)0.085 (4)0.077 (4)0.012 (4)0.014 (3)0.005 (3)
C10.153 (7)0.094 (5)0.112 (6)0.002 (5)0.039 (5)0.022 (4)
Geometric parameters (Å, º) top
S1—C31.673 (5)C10—H10A0.9300
Cl1—C81.733 (5)C6—C71.379 (7)
N2—C31.357 (6)C6—H6A0.9300
N2—N31.377 (5)C9—C81.373 (7)
N2—H2A0.8600C9—H9A0.9300
N3—C41.283 (6)C8—C71.361 (7)
C5—C101.374 (6)C7—H7A0.9300
C5—C61.379 (7)C2—C11.386 (9)
C5—C41.457 (6)C2—H2B0.9700
C4—H4A0.9300C2—H2C0.9700
N1—C31.322 (6)C1—H1B0.9600
N1—C21.439 (7)C1—H1C0.9600
N1—H1A0.8600C1—H1D0.9600
C10—C91.389 (7)
C3—N2—N3119.4 (4)N1—C3—N2116.2 (4)
C3—N2—H2A120.3N1—C3—S1124.1 (4)
N3—N2—H2A120.3N2—C3—S1119.7 (4)
C4—N3—N2116.6 (4)C7—C8—C9120.3 (5)
C10—C5—C6119.3 (4)C7—C8—Cl1120.2 (4)
C10—C5—C4119.3 (4)C9—C8—Cl1119.5 (4)
C6—C5—C4121.4 (4)C8—C7—C6120.2 (5)
N3—C4—C5120.6 (4)C8—C7—H7A119.9
N3—C4—H4A119.7C6—C7—H7A119.9
C5—C4—H4A119.7C1—C2—N1114.7 (6)
C3—N1—C2126.2 (5)C1—C2—H2B108.6
C3—N1—H1A116.9N1—C2—H2B108.6
C2—N1—H1A116.9C1—C2—H2C108.6
C5—C10—C9120.2 (5)N1—C2—H2C108.6
C5—C10—H10A119.9H2B—C2—H2C107.6
C9—C10—H10A119.9C2—C1—H1B109.5
C5—C6—C7120.3 (5)C2—C1—H1C109.5
C5—C6—H6A119.9H1B—C1—H1C109.5
C7—C6—H6A119.9C2—C1—H1D109.5
C8—C9—C10119.7 (4)H1B—C1—H1D109.5
C8—C9—H9A120.2H1C—C1—H1D109.5
C10—C9—H9A120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···S1i0.862.593.383 (4)154
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC10H12ClN3S
Mr241.75
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)4.6769 (10), 26.727 (6), 9.791 (3)
β (°) 102.59 (3)
V3)1194.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.47
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11437, 2723, 1388
Rint0.066
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.272, 1.09
No. of reflections2723
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.34

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···S1i0.862.593.383 (4)154
Symmetry code: (i) x+2, y, z+1.
 

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, Y.-F. & Meng, F.-Y. (2010). Acta Cryst. E66, o2685.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
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