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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 11| November 2011| Page o2965
doi:10.1107/S1600536811041894

1,3-Bis(2-chloro­phen­yl)thio­urea: a monoclinic polymorph

Chien Ing Yeoa and Edward R. T. Tiekinka*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 October 2011; accepted 11 October 2011; online 12 October 2011)

The title compound, C13H10Cl2N2S, represents a monoclinic polymorph of the previously reported ortho­rhom­bic form [Ramnathan et al. (1996[Ramnathan, A., Sivakumar, K., Subramanian, K., Janarthanan, N., Ramadas, K. & Fun, H.-K. (1996). Acta Cryst. C52, 134-136.]). Acta Cryst. C52, 134–136]. The mol­ecule is twisted with the dihedral angle between the benzene rings being 55.37 (7)°. The N—H atoms are syn to each other, which contrasts their anti disposition in the ortho­rhom­bic form. In the crystal, mol­ecules assemble into zigzag chains along the c axis via N—H⋯S hydrogen bonds. Chains are connected into layers via C—H⋯Cl inter­actions, and these stack along the a axis.

Related literature

For background to the structural chemistry of thio­carbamides, see: Ho et al. (2005[Ho, S. Y., Bettens, R. P. A., Dakternieks, D., Duthie, A. & Tiekink, E. R. T. (2005). CrystEngComm, 7, 682-689.]). For a related diaryl­thio­urea structure, see: Kuan & Tiekink (2007[Kuan, F. S. & Tiekink, E. R. T. (2007). Acta Cryst. E63, o4692.]). For the structure of the ortho­rhom­bic polymorph, see: Ramnathan et al. (1996[Ramnathan, A., Sivakumar, K., Subramanian, K., Janarthanan, N., Ramadas, K. & Fun, H.-K. (1996). Acta Cryst. C52, 134-136.]).

[Scheme 1]

Experimental

Crystal data

  • C13H10Cl2N2S

  • Mr = 297.19

  • Monoclinic, P 21 /c

  • a = 11.9999 (3) Å

  • b = 14.6811 (3) Å

  • c = 8.0806 (2) Å

  • β = 109.509 (1)°

  • V = 1341.84 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.62 mm−1

  • T = 100 K

  • 0.20 × 0.06 × 0.02 mm
Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.644, Tmax = 0.746

  • 12491 measured reflections

  • 3090 independent reflections

  • 2291 reflections with I > 2σ(I)

  • Rint = 0.052
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.090

  • S = 1.02

  • 3090 reflections

  • 169 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1n⋯S1i 0.87 (2) 2.62 (2) 3.4449 (18) 159 (2)
N2—H2n⋯S1i 0.87 (2) 2.49 (2) 3.3389 (18) 166 (2)
C13—H13⋯Cl2ii 0.95 2.79 3.660 (2) 152
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Qmol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041894/vm2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041894/vm2125Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041894/vm2125Isup3.cml

checkCIF report


Comment top

In connection with the synthesis and structural studies of thiocarbamides (Ho et al., 2005), diarylthioureas are sometimes isolated as the undesired hydrolysis by-product (Kuan & Tiekink, 2007). The title compound, (I), was isolated in crystalline form during the attempted synthesis of (C6H4Cl-o)N(H)C(═S)O-i-Pr. The structure of (I) is reported herein. A previously reported orthorhombic form of (I) exists in the literature (Ramnathan et al., 1996).

The molecular structure of (I), Fig. 1, is twisted about the central N—C bonds. With reference to the central plane through the CN2S chromophore [r.m.s. deviation = 0.0029 Å], the C2-benzene ring is almost perpendicular [dihedral angle = 85.20 (6)°] and the C8-ring is twisted [dihedral angle = 49.32 (6)°]; the dihedral angle between the benzene rings is 55.37 (7)°. The amide-H atoms are syn to each other. The syn conformation observed for the thiourea chromophore in (I) is quite distinct to that found in the orthorhombic polymorph (Ramnathan et al., 1996).

In the orthorhombic form of (I), the amide-H atoms are anti to each other. This key difference between the molecular structures in the two polymorphs is highlighted in the overlay diagram shown in Fig. 2. The anti orientation allows for the formation of eight-membered {···HNCS}2 synthons in the crystal packing in the orthorhombic polymorph. By contrast, the crystal structure of (I) features supramolecular zigzag chains along the c axis mediated by N—H···S hydrogen bonds (Table 1 and Fig. 3); the S1 atom is bifurcated. Chains assemble into layers by C—H···Cl interactions (Fig. 4) and the layers thus formed stack along the a axis (Fig. 5).

Related literature top

For background to the structural chemistry of thiocarbamides, see: Ho et al. (2005). For a related diarylthiourea structure, see: Kuan & Tiekink (2007). For the structure of the orthorhombic polymorph, see: Ramnathan et al. (1996).

Experimental top

2-Chlorophenyl isothiocyanate (2 ml) was added drop-wise to a stirred solution of NaOH (1 mol equiv.) in i-PrOH (25 ml) and stirred for 3 h. Excess HCl (50% M/v) was then added and the solution was stirred for a further 2 h. The product was then extracted with CHCl3 and left for evaporation at room temperature yielding colourless crystals after 3 days; M.pt: 394–396 K. IR (cm-1): ν(N—H) 3348; ν(C—N) 1498; ν(C═ S) 1201.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The N-bound H-atoms were located in a difference Fourier map but were refined with a distance restraint of N—H = 0.88±0.01 Å, and with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Overlay diagram of (I) (shown in blue) with the two independent molecules found in the orthorhombic polymorph (see text), shown in red and green. The central thiourea fragments have been fitted.
[Figure 3] Fig. 3. Supramolecular zigzag chain in (I) mediated by N—H···S hydrogen bonds, shown as orange dashed lines.
[Figure 4] Fig. 4. A view of the supramolecular two-dimensional array in the bc plane for (I). The N—H···S and C—H···Cl contacts are shown as orange and blue dashed lines, respectively.
[Figure 5] Fig. 5. Unit-cell contents for (I) shown in projection down the c axis, showing the stacking of supramolecular layers along the a axis. The N—H···S and C—H···Cl contacts are shown as orange and blue dashed lines, respectively.
1,3-Bis(2-chlorophenyl)thiourea top
Crystal data top
C13H10Cl2N2SF(000) = 608
Mr = 297.19Dx = 1.471 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2105 reflections
a = 11.9999 (3) Åθ = 2.3–25.4°
b = 14.6811 (3) ŵ = 0.62 mm−1
c = 8.0806 (2) ÅT = 100 K
β = 109.509 (1)°Prism, colourless
V = 1341.84 (5) Å30.20 × 0.06 × 0.02 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		3090 independent reflections
Radiation source: fine-focus sealed tube2291 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.644, Tmax = 0.746k = −19→19
12491 measured reflectionsl = −10→10
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0375P)2 + 0.4482P]
where P = (Fo2 + 2Fc2)/3
3090 reflections(Δ/σ)max < 0.001
169 parametersΔρmax = 0.35 e Å−3
2 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C13H10Cl2N2SV = 1341.84 (5) Å3
Mr = 297.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9999 (3) ŵ = 0.62 mm−1
b = 14.6811 (3) ÅT = 100 K
c = 8.0806 (2) Å0.20 × 0.06 × 0.02 mm
β = 109.509 (1)°
Data collection top
Bruker SMART APEX
diffractometer		3090 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2291 reflections with I > 2σ(I)
Tmin = 0.644, Tmax = 0.746Rint = 0.052
12491 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0382 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.35 e Å−3
3090 reflectionsΔρmin = −0.43 e Å−3
169 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl20.95110 (5)0.44450 (4)0.76829 (8)0.03177 (16)
Cl10.51862 (5)0.24151 (4)0.54764 (9)0.03412 (17)
S10.80893 (5)0.11833 (4)0.59792 (7)0.01789 (13)
N10.73545 (16)0.18714 (12)0.8464 (2)0.0200 (4)
H1N0.740 (2)0.2301 (12)0.923 (2)0.024*
N20.90127 (15)0.25343 (12)0.8279 (2)0.0189 (4)
H2N0.891 (2)0.2893 (13)0.907 (2)0.023*
C10.81669 (17)0.18925 (14)0.7647 (3)0.0171 (4)
C20.63988 (18)0.12309 (15)0.7997 (3)0.0192 (4)
C30.53473 (19)0.14084 (15)0.6660 (3)0.0223 (5)
C40.4428 (2)0.07777 (17)0.6227 (3)0.0280 (5)
H40.37080.09040.53110.034*
C50.4575 (2)−0.00316 (17)0.7142 (3)0.0290 (6)
H50.3955−0.04680.68450.035*
C60.5615 (2)−0.02114 (16)0.8484 (3)0.0274 (5)
H60.5708−0.07690.91120.033*
C70.6528 (2)0.04214 (15)0.8918 (3)0.0223 (5)
H70.72420.02980.98490.027*
C81.00456 (18)0.26531 (15)0.7822 (3)0.0190 (5)
C91.03988 (19)0.35296 (15)0.7568 (3)0.0227 (5)
C101.1449 (2)0.36828 (17)0.7252 (3)0.0292 (6)
H101.16870.42860.71040.035*
C111.2144 (2)0.2954 (2)0.7154 (3)0.0340 (6)
H111.28610.30540.69270.041*
C121.1804 (2)0.20762 (18)0.7386 (3)0.0308 (6)
H121.22840.15750.73030.037*
C131.07637 (19)0.19243 (16)0.7739 (3)0.0248 (5)
H131.05430.13210.79250.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0352 (3)0.0165 (3)0.0443 (4)−0.0053 (2)0.0142 (3)0.0001 (3)
Cl10.0332 (3)0.0314 (3)0.0386 (4)0.0093 (3)0.0131 (3)0.0113 (3)
S10.0192 (3)0.0152 (3)0.0199 (3)−0.0022 (2)0.0072 (2)−0.0024 (2)
N10.0229 (9)0.0184 (9)0.0211 (10)−0.0073 (8)0.0105 (8)−0.0070 (8)
N20.0195 (9)0.0151 (9)0.0231 (10)−0.0049 (7)0.0083 (8)−0.0045 (7)
C10.0179 (10)0.0135 (10)0.0179 (11)0.0006 (8)0.0034 (8)0.0024 (8)
C20.0181 (10)0.0202 (11)0.0229 (11)−0.0039 (9)0.0115 (9)−0.0062 (9)
C30.0243 (12)0.0221 (12)0.0242 (12)−0.0004 (9)0.0130 (9)−0.0013 (9)
C40.0197 (11)0.0412 (15)0.0239 (12)−0.0041 (10)0.0083 (9)−0.0069 (11)
C50.0287 (13)0.0330 (14)0.0307 (13)−0.0163 (11)0.0170 (11)−0.0129 (11)
C60.0358 (13)0.0212 (12)0.0312 (13)−0.0065 (10)0.0193 (11)−0.0015 (10)
C70.0228 (11)0.0225 (11)0.0232 (12)−0.0032 (9)0.0099 (9)−0.0019 (9)
C80.0161 (10)0.0221 (11)0.0176 (11)−0.0049 (9)0.0041 (8)−0.0021 (9)
C90.0234 (11)0.0225 (11)0.0206 (11)−0.0055 (9)0.0051 (9)−0.0026 (9)
C100.0287 (13)0.0324 (14)0.0274 (13)−0.0157 (11)0.0104 (10)−0.0035 (11)
C110.0210 (12)0.0528 (17)0.0298 (14)−0.0131 (12)0.0108 (10)−0.0079 (12)
C120.0210 (12)0.0378 (14)0.0325 (14)0.0013 (11)0.0075 (10)−0.0076 (11)
C130.0202 (11)0.0252 (12)0.0261 (12)−0.0016 (10)0.0037 (9)−0.0023 (10)
Geometric parameters (Å, º) top
Cl2—C91.737 (2)C5—H50.9500
Cl1—C31.736 (2)C6—C71.389 (3)
S1—C11.681 (2)C6—H60.9500
N1—C11.348 (3)C7—H70.9500
N1—C21.433 (3)C8—C91.391 (3)
N1—H1N0.871 (10)C8—C131.389 (3)
N2—C11.354 (3)C9—C101.385 (3)
N2—C81.417 (3)C10—C111.375 (4)
N2—H2N0.872 (9)C10—H100.9500
C2—C71.383 (3)C11—C121.383 (4)
C2—C31.384 (3)C11—H110.9500
C3—C41.392 (3)C12—C131.388 (3)
C4—C51.379 (3)C12—H120.9500
C4—H40.9500C13—H130.9500
C5—C61.379 (3)
C1—N1—C2122.16 (18)C7—C6—H6120.0
C1—N1—H1N116.2 (16)C2—C7—C6120.1 (2)
C2—N1—H1N121.4 (16)C2—C7—H7120.0
C1—N2—C8126.73 (18)C6—C7—H7120.0
C1—N2—H2N115.1 (15)C9—C8—C13118.7 (2)
C8—N2—H2N118.1 (15)C9—C8—N2119.22 (19)
N1—C1—N2113.90 (18)C13—C8—N2121.9 (2)
N1—C1—S1121.53 (16)C10—C9—C8121.2 (2)
N2—C1—S1124.56 (16)C10—C9—Cl2119.76 (18)
C7—C2—C3119.4 (2)C8—C9—Cl2119.03 (17)
C7—C2—N1119.08 (19)C11—C10—C9119.4 (2)
C3—C2—N1121.5 (2)C11—C10—H10120.3
C2—C3—C4120.7 (2)C9—C10—H10120.3
C2—C3—Cl1119.68 (17)C10—C11—C12120.4 (2)
C4—C3—Cl1119.65 (18)C10—C11—H11119.8
C5—C4—C3119.3 (2)C12—C11—H11119.8
C5—C4—H4120.3C11—C12—C13120.2 (2)
C3—C4—H4120.3C11—C12—H12119.9
C4—C5—C6120.4 (2)C13—C12—H12119.9
C4—C5—H5119.8C12—C13—C8120.1 (2)
C6—C5—H5119.8C12—C13—H13120.0
C5—C6—C7120.1 (2)C8—C13—H13120.0
C5—C6—H6120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···S1i0.87 (2)2.62 (2)3.4449 (18)159 (2)
N2—H2n···S1i0.87 (2)2.49 (2)3.3389 (18)166 (2)
C13—H13···Cl2ii0.952.793.660 (2)152
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC13H10Cl2N2S
Mr297.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)11.9999 (3), 14.6811 (3), 8.0806 (2)
β (°) 109.509 (1)
V (Å3)1341.84 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.62
Crystal size (mm)0.20 × 0.06 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.644, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		12491, 3090, 2291
Rint0.052
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.090, 1.02
No. of reflections3090
No. of parameters169
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.35, −0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···S1i0.873 (17)2.618 (17)3.4449 (18)158.6 (19)
N2—H2n···S1i0.868 (18)2.49 (2)3.3389 (18)166 (2)
C13—H13···Cl2ii0.952.793.660 (2)152
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2.
 

Acknowledgements

The Ministry of Higher Education, Malaysia, is thanked for the award of a research grant (RG125/10AFR).

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557–559.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationHo, S. Y., Bettens, R. P. A., Dakternieks, D., Duthie, A. & Tiekink, E. R. T. (2005). CrystEngComm, 7, 682–689.  Web of Science CSD CrossRef CAS Google Scholar
 First citationKuan, F. S. & Tiekink, E. R. T. (2007). Acta Cryst. E63, o4692.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRamnathan, A., Sivakumar, K., Subramanian, K., Janarthanan, N., Ramadas, K. & Fun, H.-K. (1996). Acta Cryst. C52, 134–136.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 11| November 2011| Page o2965
doi:10.1107/S1600536811041894
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