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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-(4-Chloro­benzo­yl)-3-(2,4,6-tri­chloro­phen­yl)thio­urea hemihydrate

aDepartment of Chemistry, Quaid-i-Azam University Islamabad, 45320-Pakistan, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: aminbadshah@yahoo.com

(Received 2 December 2008; accepted 6 December 2008; online 17 December 2008)

The asymmetric unit of the title compound, C14H8Cl4N2OS·0.5H2O, contains two independent mol­ecules with different conformations with respect to the aromatic ring planes, and one water mol­ecule. The bond lengths and angles are typical of thio­urea compounds of this class. The mol­ecule exists in the solid state in its thione form with typical thio­urea C—S and C—O bonds lengths, as well as shortened C—N bonds. The dihedral angles between the two aromatic planes are 66.93 (8) and 60.44 (9)° in the two independent mol­ecules. An intra­molecular N—H⋯O hydrogen bond stabilizes the mol­ecular conformation and the crystal packing is characterized by N—H⋯O, O—H⋯S and O—H⋯Cl hydrogen bonds.

Related literature

For background and related structures, see: Khawar Rauf et al. (2006a[Khawar Rauf, M., Badshah, A., Bolte, M. & Zaeem Akhtar, M. (2006a). Acta Cryst. E62, o1849-o1850.],b[Khawar Rauf, M., Badshah, A. & Bolte, M. (2006b). Acta Cryst. E62, o1859-o1860.],c[Khawar Rauf, M., Badshah, A. & Bolte, M. (2006c). Acta Cryst. E62, o2221-o2222.],d[Khawar Rauf, M., Badshah, A. & Bolte, M. (2006d). Acta Cryst. E62, o2444-o2445.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8Cl4N2OS·0.5H2O

  • Mr = 403.09

  • Monoclinic, P 21 /c

  • a = 16.1428 (9) Å

  • b = 13.7340 (7) Å

  • c = 16.2850 (9) Å

  • β = 112.216 (4)°

  • V = 3342.4 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.84 mm−1

  • T = 173 (2) K

  • 0.38 × 0.37 × 0.35 mm

Data collection
  • STOE IPDS II two-circle-diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.741, Tmax = 0.758

  • 23391 measured reflections

  • 7172 independent reflections

  • 5964 reflections with I > 2σ(I)

  • Rint = 0.068

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.125

  • S = 1.02

  • 7172 reflections

  • 428 parameters

  • 7 restraints

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

  • Δρmax = 0.94 e Å−3

  • Δρmin = −0.60 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1W 0.866 (10) 2.211 (17) 2.997 (3) 151 (3)
N2—H2⋯O1 0.873 (10) 1.97 (2) 2.627 (2) 131 (3)
N2—H2⋯O1Ai 0.873 (10) 2.26 (2) 2.931 (3) 133 (2)
N1A—H1A⋯O1W 0.874 (10) 1.964 (13) 2.816 (3) 164 (3)
N2A—H2A⋯O1A 0.877 (10) 1.98 (3) 2.637 (3) 130 (3)
N2A—H2A⋯O1ii 0.877 (10) 2.31 (2) 3.001 (3) 136 (3)
O1W—H1WA⋯S1A 0.855 (10) 2.67 (3) 3.215 (2) 123 (3)
O1W—H1WA⋯Cl3iii 0.855 (10) 2.84 (3) 3.388 (2) 123 (3)
O1W—H1WB⋯S1 0.855 (10) 2.36 (2) 3.091 (2) 144 (3)
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) -x, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Khawar Rauf et al., 2006a, 2006b, 2006c, 2006d). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the two independent molecules is given in Fig. 1.The water molecule links the molecules through OW—H···S and N—H···OW hydrogen bonds. Bond lengths and angles, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al.,2006b).The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths.The thiocarbonyl and carbonyl groups are almost coplanar. An intramolecular N—H···O hydrogen bond is present, forming a six membered ring commonly observed in this class of compounds (Khawar Rauf et al., 2006a). The the crystal packing is stabilized by intermolecular N—H···O, O—H···S and O—H···Cl hydrogen bonds (Table 1).

Related literature top

For background and related structures, see: Khawar Rauf et al. (2006a,b,c,d). For a description of the Cambridge Structural Databasde, see: Allen (2002).

Experimental top

Freshly prepared 4-chlorobenzoyl isothiocyanate (2.0 g, 10 mmol) was stirred in acetone (40 ml) for 15 minutes. Neat 3,5-dichloroaniline (1.62 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ 1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 85%. Full spectroscopic and physical characterization will be reported elsewhere.

Refinement top

Hydrogen atoms bonded to C were included in calculated positions and refined as riding on their parent C atom with C—H = 0.95 Å Uiso(H) = 1.2Ueq(C). The H atoms bonded to N were refined with the N—H distances restrained to 0.88 (1) Å. The water H atoms were refined with the O—H distances restrained to 0.83 (1)Å and the H···H distances restrained to 1.40 (5)Å and with Uiso(H) = 1.2Ueq(O).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing the atom numbering scheme. Intra- and intermolecular hydrogen bonds are shown as dash lines. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I).
1-(4-Chlorobenzoyl)-3-(2,4,6-trichlorophenyl)thiourea hemihydrate top
Crystal data top
C14H8Cl4N2OS·0.5H2OF(000) = 1624
Mr = 403.09Dx = 1.602 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 21741 reflections
a = 16.1428 (9) Åθ = 2.2–27.1°
b = 13.7340 (7) ŵ = 0.84 mm1
c = 16.2850 (9) ÅT = 173 K
β = 112.216 (4)°Block, colourless
V = 3342.4 (3) Å30.38 × 0.37 × 0.35 mm
Z = 8
Data collection top
STOE IPDS II two-circle-
diffractometer
7172 independent reflections
Radiation source: fine-focus sealed tube5964 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
ω scansθmax = 26.9°, θmin = 2.1°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1720
Tmin = 0.741, Tmax = 0.758k = 1717
23391 measured reflectionsl = 2020
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0647P)2 + 1.5427P]
where P = (Fo2 + 2Fc2)/3
7172 reflections(Δ/σ)max = 0.001
428 parametersΔρmax = 0.94 e Å3
7 restraintsΔρmin = 0.60 e Å3
Crystal data top
C14H8Cl4N2OS·0.5H2OV = 3342.4 (3) Å3
Mr = 403.09Z = 8
Monoclinic, P21/cMo Kα radiation
a = 16.1428 (9) ŵ = 0.84 mm1
b = 13.7340 (7) ÅT = 173 K
c = 16.2850 (9) Å0.38 × 0.37 × 0.35 mm
β = 112.216 (4)°
Data collection top
STOE IPDS II two-circle-
diffractometer
7172 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
5964 reflections with I > 2σ(I)
Tmin = 0.741, Tmax = 0.758Rint = 0.068
23391 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0457 restraints
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.94 e Å3
7172 reflectionsΔρmin = 0.60 e Å3
428 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
C10.37638 (14)0.52532 (16)0.57504 (15)0.0302 (5)
O10.38255 (10)0.53995 (13)0.50312 (11)0.0357 (4)
N10.29511 (12)0.50614 (15)0.58141 (13)0.0324 (4)
H10.2955 (19)0.497 (2)0.6343 (10)0.041 (8)*
C20.21054 (14)0.50210 (17)0.51379 (15)0.0325 (5)
N20.20766 (12)0.52155 (15)0.43208 (13)0.0332 (4)
H20.2559 (13)0.537 (2)0.4227 (19)0.045 (8)*
S10.12057 (4)0.47441 (6)0.53583 (4)0.04717 (18)
Cl10.71014 (4)0.55572 (5)0.90337 (4)0.04341 (16)
Cl20.15939 (5)0.34487 (6)0.31698 (6)0.0673 (2)
Cl30.13692 (5)0.54231 (9)0.12131 (5)0.0773 (3)
Cl40.11099 (5)0.71115 (5)0.40822 (5)0.05120 (18)
C110.45662 (14)0.52864 (16)0.65923 (15)0.0295 (4)
C120.45243 (15)0.53432 (17)0.74359 (15)0.0333 (5)
H120.39600.53320.74920.040*
C130.53058 (16)0.54156 (18)0.81928 (15)0.0355 (5)
H130.52780.54540.87640.043*
C140.61249 (15)0.54311 (17)0.80970 (15)0.0337 (5)
C150.61818 (15)0.53658 (18)0.72711 (16)0.0359 (5)
H150.67480.53740.72190.043*
C160.54017 (15)0.52882 (17)0.65206 (15)0.0332 (5)
H160.54360.52360.59530.040*
C210.12477 (14)0.52657 (18)0.35815 (15)0.0335 (5)
C220.09467 (16)0.44876 (19)0.29937 (18)0.0406 (6)
C230.01410 (17)0.4524 (2)0.22662 (18)0.0473 (7)
H230.00590.39860.18740.057*
C240.03568 (16)0.5362 (2)0.21313 (18)0.0492 (7)
C250.00886 (16)0.6165 (2)0.26850 (18)0.0461 (6)
H250.04470.67350.25770.055*
C260.07260 (15)0.61070 (19)0.34072 (16)0.0371 (5)
C1A0.24641 (14)0.78726 (17)0.78708 (15)0.0314 (5)
O1A0.28145 (10)0.86354 (12)0.82401 (11)0.0359 (4)
N1A0.27773 (12)0.69679 (15)0.82106 (13)0.0328 (4)
H1A0.2541 (18)0.6458 (14)0.7884 (16)0.044 (8)*
C2A0.34638 (14)0.67443 (17)0.90195 (15)0.0313 (5)
N2A0.38814 (13)0.75109 (15)0.95146 (13)0.0344 (4)
H2A0.374 (2)0.8114 (10)0.934 (2)0.052 (9)*
S1A0.37231 (4)0.55898 (5)0.93165 (4)0.03769 (15)
Cl1A0.07853 (4)0.81919 (6)0.45000 (5)0.05347 (19)
Cl2A0.57143 (5)0.76385 (6)0.94715 (5)0.05124 (18)
Cl3A0.68978 (5)0.70470 (5)1.29886 (5)0.0547 (2)
Cl4A0.33577 (4)0.72377 (6)1.10872 (5)0.04826 (17)
C11A0.16642 (14)0.78908 (17)0.70221 (15)0.0313 (5)
C12A0.10421 (16)0.71386 (19)0.67392 (17)0.0386 (5)
H12A0.11360.65570.70790.046*
C13A0.02828 (16)0.7229 (2)0.59643 (17)0.0419 (6)
H13A0.01440.67170.57780.050*
C14A0.01600 (15)0.8069 (2)0.54725 (16)0.0387 (5)
C15A0.07758 (16)0.8833 (2)0.57343 (17)0.0425 (6)
H15A0.06860.94050.53840.051*
C16A0.15197 (15)0.87407 (18)0.65141 (16)0.0369 (5)
H16A0.19370.92610.67060.044*
C21A0.45990 (15)0.73872 (17)1.03485 (15)0.0332 (5)
C22A0.54822 (16)0.74224 (18)1.04103 (16)0.0357 (5)
C23A0.61967 (16)0.72962 (18)1.12165 (18)0.0405 (6)
H23A0.67960.73041.12480.049*
C24A0.60090 (17)0.71594 (18)1.19714 (17)0.0401 (6)
C25A0.51466 (17)0.71352 (18)1.19431 (16)0.0389 (5)
H25A0.50320.70421.24690.047*
C26A0.44472 (15)0.72506 (17)1.11274 (16)0.0346 (5)
O1W0.23342 (15)0.51628 (16)0.73321 (13)0.0524 (5)
H1WA0.250 (2)0.487 (2)0.7831 (12)0.063*
H1WB0.1870 (15)0.495 (2)0.6911 (16)0.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0239 (10)0.0309 (11)0.0321 (11)0.0011 (8)0.0063 (8)0.0005 (9)
O10.0247 (7)0.0512 (10)0.0287 (8)0.0024 (7)0.0073 (6)0.0029 (7)
N10.0257 (9)0.0420 (11)0.0255 (9)0.0055 (8)0.0054 (7)0.0023 (8)
C20.0249 (10)0.0349 (11)0.0321 (11)0.0035 (9)0.0045 (8)0.0004 (9)
N20.0203 (8)0.0445 (11)0.0294 (10)0.0007 (8)0.0033 (7)0.0021 (8)
S10.0294 (3)0.0704 (5)0.0407 (3)0.0145 (3)0.0121 (3)0.0018 (3)
Cl10.0274 (3)0.0557 (4)0.0352 (3)0.0004 (2)0.0016 (2)0.0011 (3)
Cl20.0476 (4)0.0498 (4)0.0882 (6)0.0034 (3)0.0070 (4)0.0203 (4)
Cl30.0285 (3)0.1409 (9)0.0451 (4)0.0121 (4)0.0059 (3)0.0145 (5)
Cl40.0482 (4)0.0483 (4)0.0538 (4)0.0070 (3)0.0156 (3)0.0073 (3)
C110.0243 (10)0.0318 (11)0.0283 (11)0.0001 (8)0.0051 (8)0.0008 (9)
C120.0244 (10)0.0415 (12)0.0309 (11)0.0046 (9)0.0069 (8)0.0018 (10)
C130.0325 (11)0.0442 (13)0.0266 (11)0.0031 (10)0.0074 (9)0.0009 (10)
C140.0266 (10)0.0337 (11)0.0328 (12)0.0005 (9)0.0022 (9)0.0001 (9)
C150.0239 (10)0.0450 (13)0.0357 (12)0.0045 (9)0.0076 (9)0.0004 (10)
C160.0266 (10)0.0403 (12)0.0310 (11)0.0042 (9)0.0091 (9)0.0000 (9)
C210.0193 (9)0.0481 (13)0.0278 (11)0.0036 (9)0.0030 (8)0.0015 (10)
C220.0274 (11)0.0459 (14)0.0442 (14)0.0050 (10)0.0088 (10)0.0036 (11)
C230.0320 (12)0.0644 (18)0.0400 (14)0.0158 (12)0.0072 (10)0.0089 (13)
C240.0245 (11)0.079 (2)0.0371 (13)0.0095 (12)0.0043 (10)0.0078 (13)
C250.0254 (11)0.0633 (17)0.0447 (14)0.0073 (11)0.0078 (10)0.0131 (13)
C260.0259 (10)0.0467 (14)0.0363 (12)0.0020 (10)0.0090 (9)0.0027 (11)
C1A0.0234 (10)0.0387 (12)0.0305 (11)0.0002 (9)0.0084 (8)0.0006 (9)
O1A0.0302 (8)0.0364 (9)0.0341 (8)0.0032 (7)0.0043 (6)0.0006 (7)
N1A0.0277 (9)0.0350 (10)0.0300 (10)0.0005 (8)0.0045 (7)0.0024 (8)
C2A0.0239 (10)0.0400 (12)0.0288 (11)0.0017 (9)0.0084 (8)0.0006 (9)
N2A0.0297 (9)0.0375 (11)0.0272 (9)0.0005 (8)0.0008 (8)0.0005 (8)
S1A0.0343 (3)0.0375 (3)0.0342 (3)0.0004 (2)0.0049 (2)0.0024 (2)
Cl1A0.0317 (3)0.0725 (5)0.0405 (3)0.0089 (3)0.0041 (2)0.0019 (3)
Cl2A0.0459 (4)0.0694 (5)0.0421 (3)0.0076 (3)0.0207 (3)0.0047 (3)
Cl3A0.0466 (4)0.0533 (4)0.0410 (4)0.0015 (3)0.0098 (3)0.0064 (3)
Cl4A0.0348 (3)0.0623 (4)0.0491 (4)0.0024 (3)0.0173 (3)0.0007 (3)
C11A0.0233 (10)0.0395 (12)0.0289 (11)0.0003 (9)0.0073 (8)0.0008 (9)
C12A0.0285 (11)0.0437 (13)0.0362 (12)0.0029 (10)0.0037 (9)0.0037 (10)
C13A0.0290 (11)0.0490 (14)0.0396 (13)0.0052 (10)0.0038 (10)0.0033 (11)
C14A0.0254 (10)0.0526 (15)0.0326 (12)0.0073 (10)0.0049 (9)0.0016 (11)
C15A0.0351 (12)0.0481 (14)0.0400 (13)0.0070 (11)0.0094 (10)0.0071 (11)
C16A0.0275 (10)0.0403 (13)0.0383 (12)0.0005 (9)0.0073 (9)0.0012 (10)
C21A0.0288 (11)0.0338 (11)0.0303 (11)0.0003 (9)0.0035 (9)0.0011 (9)
C22A0.0314 (11)0.0377 (12)0.0339 (12)0.0021 (9)0.0077 (9)0.0026 (10)
C23A0.0273 (11)0.0412 (13)0.0454 (14)0.0015 (9)0.0052 (10)0.0031 (11)
C24A0.0385 (13)0.0328 (12)0.0359 (12)0.0004 (10)0.0009 (10)0.0013 (10)
C25A0.0428 (13)0.0375 (13)0.0311 (12)0.0013 (10)0.0078 (10)0.0023 (10)
C26A0.0282 (11)0.0373 (12)0.0335 (12)0.0003 (9)0.0064 (9)0.0008 (10)
O1W0.0528 (12)0.0601 (13)0.0406 (11)0.0075 (10)0.0133 (9)0.0067 (9)
Geometric parameters (Å, º) top
C1—O11.229 (3)C1A—N1A1.376 (3)
C1—N11.380 (3)C1A—C11A1.493 (3)
C1—C111.489 (3)N1A—C2A1.398 (3)
N1—C21.394 (3)N1A—H1A0.874 (10)
N1—H10.866 (10)C2A—N2A1.342 (3)
C2—N21.341 (3)C2A—S1A1.664 (2)
C2—S11.666 (2)N2A—C21A1.423 (3)
N2—C211.424 (3)N2A—H2A0.877 (10)
N2—H20.873 (10)Cl1A—C14A1.743 (2)
Cl1—C141.739 (2)Cl2A—C22A1.732 (3)
Cl2—C221.727 (3)Cl3A—C24A1.741 (2)
Cl3—C241.751 (3)Cl4A—C26A1.735 (2)
Cl4—C261.726 (3)C11A—C12A1.392 (3)
C11—C161.397 (3)C11A—C16A1.398 (3)
C11—C121.403 (3)C12A—C13A1.393 (3)
C12—C131.395 (3)C12A—H12A0.9500
C12—H120.9500C13A—C14A1.376 (4)
C13—C141.389 (3)C13A—H13A0.9500
C13—H130.9500C14A—C15A1.396 (4)
C14—C151.385 (3)C15A—C16A1.385 (3)
C15—C161.388 (3)C15A—H15A0.9500
C15—H150.9500C16A—H16A0.9500
C16—H160.9500C21A—C26A1.393 (3)
C21—C221.394 (4)C21A—C22A1.392 (3)
C21—C261.394 (3)C22A—C23A1.392 (3)
C22—C231.390 (4)C23A—C24A1.386 (4)
C23—C241.372 (4)C23A—H23A0.9500
C23—H230.9500C24A—C25A1.376 (4)
C24—C251.386 (4)C25A—C26A1.389 (3)
C25—C261.396 (3)C25A—H25A0.9500
C25—H250.9500O1W—H1WA0.855 (10)
C1A—O1A1.234 (3)O1W—H1WB0.855 (10)
O1—C1—N1121.66 (19)O1A—C1A—C11A120.9 (2)
O1—C1—C11121.1 (2)N1A—C1A—C11A116.4 (2)
N1—C1—C11117.2 (2)C1A—N1A—C2A128.1 (2)
C1—N1—C2128.6 (2)C1A—N1A—H1A118.0 (19)
C1—N1—H1116.8 (19)C2A—N1A—H1A113.9 (19)
C2—N1—H1114.6 (19)N2A—C2A—N1A115.6 (2)
N2—C2—N1115.6 (2)N2A—C2A—S1A123.96 (17)
N2—C2—S1123.59 (16)N1A—C2A—S1A120.39 (17)
N1—C2—S1120.80 (18)C2A—N2A—C21A121.5 (2)
C2—N2—C21121.19 (19)C2A—N2A—H2A122 (2)
C2—N2—H2121 (2)C21A—N2A—H2A116 (2)
C21—N2—H2117 (2)C12A—C11A—C16A119.0 (2)
C16—C11—C12119.2 (2)C12A—C11A—C1A123.9 (2)
C16—C11—C1117.0 (2)C16A—C11A—C1A117.0 (2)
C12—C11—C1123.8 (2)C11A—C12A—C13A120.8 (2)
C13—C12—C11120.5 (2)C11A—C12A—H12A119.6
C13—C12—H12119.8C13A—C12A—H12A119.6
C11—C12—H12119.8C14A—C13A—C12A119.1 (2)
C14—C13—C12118.9 (2)C14A—C13A—H13A120.5
C14—C13—H13120.6C12A—C13A—H13A120.5
C12—C13—H13120.6C13A—C14A—C15A121.5 (2)
C15—C14—C13121.6 (2)C13A—C14A—Cl1A119.6 (2)
C15—C14—Cl1119.17 (18)C15A—C14A—Cl1A118.9 (2)
C13—C14—Cl1119.25 (19)C16A—C15A—C14A118.8 (2)
C14—C15—C16119.3 (2)C16A—C15A—H15A120.6
C14—C15—H15120.4C14A—C15A—H15A120.6
C16—C15—H15120.4C15A—C16A—C11A120.8 (2)
C15—C16—C11120.6 (2)C15A—C16A—H16A119.6
C15—C16—H16119.7C11A—C16A—H16A119.6
C11—C16—H16119.7C26A—C21A—C22A117.8 (2)
C22—C21—C26117.9 (2)C26A—C21A—N2A121.7 (2)
C22—C21—N2121.1 (2)C22A—C21A—N2A120.5 (2)
C26—C21—N2121.0 (2)C21A—C22A—C23A121.6 (2)
C23—C22—C21121.9 (3)C21A—C22A—Cl2A119.99 (18)
C23—C22—Cl2118.9 (2)C23A—C22A—Cl2A118.4 (2)
C21—C22—Cl2119.17 (18)C24A—C23A—C22A118.2 (2)
C24—C23—C22118.0 (3)C24A—C23A—H23A120.9
C24—C23—H23121.0C22A—C23A—H23A120.9
C22—C23—H23121.0C25A—C24A—C23A122.1 (2)
C23—C24—C25122.9 (2)C25A—C24A—Cl3A119.3 (2)
C23—C24—Cl3118.6 (2)C23A—C24A—Cl3A118.6 (2)
C25—C24—Cl3118.6 (2)C24A—C25A—C26A118.4 (2)
C24—C25—C26117.8 (3)C24A—C25A—H25A120.8
C24—C25—H25121.1C26A—C25A—H25A120.8
C26—C25—H25121.1C25A—C26A—C21A121.8 (2)
C21—C26—C25121.5 (2)C25A—C26A—Cl4A118.7 (2)
C21—C26—Cl4119.26 (17)C21A—C26A—Cl4A119.46 (17)
C25—C26—Cl4119.2 (2)H1WA—O1W—H1WB118 (3)
O1A—C1A—N1A122.7 (2)
O1—C1—N1—C21.6 (4)O1A—C1A—N1A—C2A5.1 (4)
C11—C1—N1—C2177.8 (2)C11A—C1A—N1A—C2A174.6 (2)
C1—N1—C2—N21.6 (4)C1A—N1A—C2A—N2A1.7 (3)
C1—N1—C2—S1178.25 (19)C1A—N1A—C2A—S1A178.52 (19)
N1—C2—N2—C21175.6 (2)N1A—C2A—N2A—C21A179.3 (2)
S1—C2—N2—C214.6 (3)S1A—C2A—N2A—C21A0.4 (3)
O1—C1—C11—C1612.9 (3)O1A—C1A—C11A—C12A155.0 (2)
N1—C1—C11—C16167.7 (2)N1A—C1A—C11A—C12A24.7 (3)
O1—C1—C11—C12165.2 (2)O1A—C1A—C11A—C16A21.6 (3)
N1—C1—C11—C1214.1 (3)N1A—C1A—C11A—C16A158.7 (2)
C16—C11—C12—C131.0 (4)C16A—C11A—C12A—C13A0.3 (4)
C1—C11—C12—C13177.1 (2)C1A—C11A—C12A—C13A176.2 (2)
C11—C12—C13—C140.0 (4)C11A—C12A—C13A—C14A0.9 (4)
C12—C13—C14—C150.7 (4)C12A—C13A—C14A—C15A0.3 (4)
C12—C13—C14—Cl1178.12 (19)C12A—C13A—C14A—Cl1A179.9 (2)
C13—C14—C15—C160.3 (4)C13A—C14A—C15A—C16A0.9 (4)
Cl1—C14—C15—C16178.50 (19)Cl1A—C14A—C15A—C16A179.0 (2)
C14—C15—C16—C110.7 (4)C14A—C15A—C16A—C11A1.4 (4)
C12—C11—C16—C151.4 (4)C12A—C11A—C16A—C15A0.8 (4)
C1—C11—C16—C15176.9 (2)C1A—C11A—C16A—C15A177.6 (2)
C2—N2—C21—C22100.5 (3)C2A—N2A—C21A—C26A85.7 (3)
C2—N2—C21—C2681.6 (3)C2A—N2A—C21A—C22A95.8 (3)
C26—C21—C22—C231.8 (4)C26A—C21A—C22A—C23A2.0 (4)
N2—C21—C22—C23179.8 (2)N2A—C21A—C22A—C23A179.5 (2)
C26—C21—C22—Cl2177.95 (19)C26A—C21A—C22A—Cl2A177.46 (18)
N2—C21—C22—Cl20.0 (3)N2A—C21A—C22A—Cl2A1.1 (3)
C21—C22—C23—C240.7 (4)C21A—C22A—C23A—C24A1.8 (4)
Cl2—C22—C23—C24179.1 (2)Cl2A—C22A—C23A—C24A177.66 (19)
C22—C23—C24—C250.2 (4)C22A—C23A—C24A—C25A0.7 (4)
C22—C23—C24—Cl3179.5 (2)C22A—C23A—C24A—Cl3A177.60 (19)
C23—C24—C25—C260.1 (4)C23A—C24A—C25A—C26A0.1 (4)
Cl3—C24—C25—C26179.2 (2)Cl3A—C24A—C25A—C26A178.41 (19)
C22—C21—C26—C252.1 (4)C24A—C25A—C26A—C21A0.1 (4)
N2—C21—C26—C25179.9 (2)C24A—C25A—C26A—Cl4A179.14 (19)
C22—C21—C26—Cl4176.13 (19)C22A—C21A—C26A—C25A1.1 (4)
N2—C21—C26—Cl41.8 (3)N2A—C21A—C26A—C25A179.6 (2)
C24—C25—C26—C211.3 (4)C22A—C21A—C26A—Cl4A178.12 (18)
C24—C25—C26—Cl4176.9 (2)N2A—C21A—C26A—Cl4A0.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1W0.87 (1)2.21 (2)2.997 (3)151 (3)
N2—H2···O10.87 (1)1.97 (2)2.627 (2)131 (3)
N2—H2···O1Ai0.87 (1)2.26 (2)2.931 (3)133 (2)
N1A—H1A···O1W0.87 (1)1.96 (1)2.816 (3)164 (3)
N2A—H2A···O1A0.88 (1)1.98 (3)2.637 (3)130 (3)
N2A—H2A···O1ii0.88 (1)2.31 (2)3.001 (3)136 (3)
O1W—H1WA···S1A0.86 (1)2.67 (3)3.215 (2)123 (3)
O1W—H1WA···Cl3iii0.86 (1)2.84 (3)3.388 (2)123 (3)
O1W—H1WB···S10.86 (1)2.36 (2)3.091 (2)144 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2; (iii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC14H8Cl4N2OS·0.5H2O
Mr403.09
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)16.1428 (9), 13.7340 (7), 16.2850 (9)
β (°) 112.216 (4)
V3)3342.4 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.84
Crystal size (mm)0.38 × 0.37 × 0.35
Data collection
DiffractometerSTOE IPDS II two-circle-
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.741, 0.758
No. of measured, independent and
observed [I > 2σ(I)] reflections
23391, 7172, 5964
Rint0.068
(sin θ/λ)max1)0.637
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.125, 1.02
No. of reflections7172
No. of parameters428
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.94, 0.60

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1W0.866 (10)2.211 (17)2.997 (3)151 (3)
N2—H2···O10.873 (10)1.97 (2)2.627 (2)131 (3)
N2—H2···O1Ai0.873 (10)2.26 (2)2.931 (3)133 (2)
N1A—H1A···O1W0.874 (10)1.964 (13)2.816 (3)164 (3)
N2A—H2A···O1A0.877 (10)1.98 (3)2.637 (3)130 (3)
N2A—H2A···O1ii0.877 (10)2.31 (2)3.001 (3)136 (3)
O1W—H1WA···S1A0.855 (10)2.67 (3)3.215 (2)123 (3)
O1W—H1WA···Cl3iii0.855 (10)2.84 (3)3.388 (2)123 (3)
O1W—H1WB···S10.855 (10)2.36 (2)3.091 (2)144 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2; (iii) x, y+1, z+1.
 

Acknowledgements

MKR is grateful to the HEC-Pakistan for financial support for the PhD program under scholarship No. ILC–0363104.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationKhawar Rauf, M., Badshah, A. & Bolte, M. (2006b). Acta Cryst. E62, o1859–o1860.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKhawar Rauf, M., Badshah, A. & Bolte, M. (2006c). Acta Cryst. E62, o2221–o2222.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKhawar Rauf, M., Badshah, A. & Bolte, M. (2006d). Acta Cryst. E62, o2444–o2445.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKhawar Rauf, M., Badshah, A., Bolte, M. & Zaeem Akhtar, M. (2006a). Acta Cryst. E62, o1849–o1850.  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
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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