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The title compound, C15H11ClN2S, has been prepared by the reaction of Lawesson's reagent with N-(2-chloro­benzoyl)-N′-(4-methyl­benzoyl)­hydrazine, under microwave irradiation and in the absence of solvent. It crystallizes with two mol­ecules per asymmetric unit and X-ray analysis reveals that the three rings in both mol­ecules are nearly coplanar. The mol­ecules form stacks, in a head-to-tail manner, with intermolecular π–π interactions. Intermolecular C—H...N hydrogen bonds are also present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009742/wn6242sup1.cif
Contains datablocks 021129a, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009742/wn6242Isup2.hkl
Contains datablock I

CCDC reference: 239290

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.058
  • wR factor = 0.126
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... N1 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 19978); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

5-(2-Chlorophenyl)-2-p-tolyl-1,3,4-thiadiazole top
Crystal data top
C15H11ClN2SF(000) = 1184
Mr = 286.77Dx = 1.388 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.968 (5) ÅCell parameters from 998 reflections
b = 14.602 (5) Åθ = 3.0–22.1°
c = 15.271 (4) ŵ = 0.42 mm1
β = 118.24 (2)°T = 293 K
V = 2744.0 (15) Å3Block, colorless
Z = 80.40 × 0.25 × 0.25 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4801 independent reflections
Radiation source: fine-focus sealed tube2142 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1016
Tmin = 0.767, Tmax = 0.901k = 1716
9474 measured reflectionsl = 186
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
4801 reflections(Δ/σ)max < 0.001
346 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. IR spectra were obtained on a Shimadzu-IR 435 spectrometer. 1H NMR spectra were recorded on a Bruker AC—P200 spectrometer with TMS as the internal standard. Elemental analysis was performed on a Yanaco MT-3 instrument. Melting points were determined with a Yanaco MP-500 apparatus and uncorrected.

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
Cl10.34759 (9)0.67047 (8)0.10227 (9)0.0778 (4)
Cl20.84191 (9)0.09952 (8)0.08796 (10)0.0840 (4)
S10.18121 (8)0.54810 (8)0.11716 (8)0.0548 (3)
S20.66900 (9)0.01735 (7)0.10105 (8)0.0544 (3)
N10.0695 (3)0.6476 (3)0.1702 (3)0.0736 (12)
N20.0306 (3)0.5597 (3)0.1639 (3)0.0713 (11)
N30.5294 (3)0.0013 (2)0.1626 (3)0.0607 (10)
N40.5708 (3)0.0848 (2)0.1666 (3)0.0657 (11)
C10.1115 (3)0.3404 (3)0.1017 (3)0.0665 (13)
H10.16840.36020.09100.080*
C20.0847 (4)0.2475 (3)0.0926 (3)0.0740 (14)
H20.12430.20640.07590.089*
C30.0011 (4)0.2152 (3)0.1078 (3)0.0692 (14)
C40.0556 (4)0.2788 (3)0.1309 (3)0.0700 (14)
H40.11320.25910.14060.084*
C50.0307 (3)0.3703 (3)0.1405 (3)0.0645 (13)
H50.07120.41090.15670.077*
C60.0544 (3)0.4028 (3)0.1263 (3)0.0458 (11)
C70.0806 (3)0.5012 (3)0.1373 (3)0.0442 (10)
C80.1481 (3)0.6533 (3)0.1471 (3)0.0448 (10)
C90.1968 (3)0.7432 (3)0.1492 (3)0.0481 (11)
C100.1515 (3)0.8198 (3)0.1713 (3)0.0656 (13)
H100.09240.81190.18280.079*
C110.1927 (4)0.9063 (3)0.1762 (4)0.0823 (15)
H110.16190.95590.19190.099*
C120.2786 (4)0.9199 (4)0.1582 (4)0.0829 (16)
H120.30600.97860.16170.099*
C130.3246 (4)0.8469 (4)0.1350 (3)0.0712 (14)
H130.38280.85620.12240.085*
C140.2836 (3)0.7587 (3)0.1305 (3)0.0533 (12)
C150.0254 (4)0.1144 (3)0.1001 (4)0.0978 (18)
H15A0.00390.09020.16520.147*
H15B0.01290.08290.07100.147*
H15C0.10220.10600.05910.147*
C160.5979 (3)0.2266 (3)0.0973 (3)0.0568 (12)
H160.65610.20980.08710.068*
C170.5683 (4)0.3173 (3)0.0901 (3)0.0652 (13)
H170.60670.36060.07460.078*
C180.4830 (4)0.3459 (3)0.1054 (3)0.0613 (12)
C190.4279 (4)0.2788 (3)0.1280 (3)0.0676 (13)
H190.37030.29590.13890.081*
C200.4557 (3)0.1880 (3)0.1346 (3)0.0606 (12)
H200.41640.14480.14930.073*
C210.5419 (3)0.1598 (3)0.1196 (3)0.0453 (11)
C220.5737 (3)0.0624 (3)0.1303 (3)0.0432 (10)
C230.6433 (3)0.0882 (3)0.1361 (3)0.0455 (10)
C240.6944 (3)0.1773 (3)0.1355 (3)0.0482 (11)
C250.6521 (3)0.2559 (3)0.1569 (3)0.0638 (13)
H250.59280.25020.16850.077*
C260.6957 (4)0.3413 (3)0.1612 (3)0.0753 (15)
H260.66640.39210.17660.090*
C270.7825 (4)0.3518 (3)0.1429 (3)0.0767 (15)
H270.81120.40970.14510.092*
C280.8264 (3)0.2767 (3)0.1213 (3)0.0671 (13)
H280.88580.28340.10980.080*
C290.7821 (3)0.1910 (3)0.1167 (3)0.0547 (12)
C300.4504 (4)0.4449 (3)0.0998 (3)0.0854 (16)
H30A0.49580.48180.08250.128*
H30B0.45870.46410.16320.128*
H30C0.37590.45190.05020.128*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0690 (8)0.0856 (10)0.1022 (10)0.0069 (7)0.0598 (8)0.0087 (8)
Cl20.0796 (9)0.0713 (9)0.1322 (12)0.0056 (7)0.0757 (9)0.0044 (8)
S10.0505 (7)0.0560 (8)0.0680 (8)0.0023 (6)0.0363 (7)0.0009 (6)
S20.0560 (7)0.0518 (7)0.0671 (8)0.0019 (6)0.0387 (7)0.0021 (6)
N10.069 (3)0.054 (3)0.127 (4)0.000 (2)0.069 (3)0.005 (2)
N20.063 (3)0.057 (3)0.116 (3)0.003 (2)0.061 (3)0.000 (2)
N30.057 (2)0.055 (3)0.086 (3)0.004 (2)0.046 (2)0.008 (2)
N40.068 (3)0.053 (3)0.098 (3)0.004 (2)0.058 (3)0.006 (2)
C10.061 (3)0.064 (4)0.081 (4)0.000 (3)0.038 (3)0.004 (3)
C20.086 (4)0.054 (4)0.082 (4)0.011 (3)0.040 (3)0.009 (3)
C30.078 (4)0.056 (3)0.052 (3)0.003 (3)0.013 (3)0.007 (3)
C40.065 (3)0.070 (4)0.078 (4)0.008 (3)0.037 (3)0.011 (3)
C50.065 (3)0.054 (3)0.081 (4)0.001 (3)0.040 (3)0.008 (3)
C60.040 (3)0.052 (3)0.040 (3)0.006 (2)0.014 (2)0.008 (2)
C70.034 (2)0.053 (3)0.044 (2)0.006 (2)0.017 (2)0.008 (2)
C80.036 (2)0.051 (3)0.045 (3)0.006 (2)0.018 (2)0.005 (2)
C90.037 (3)0.057 (3)0.045 (3)0.001 (2)0.015 (2)0.004 (2)
C100.056 (3)0.055 (3)0.085 (4)0.007 (3)0.033 (3)0.005 (3)
C110.077 (4)0.053 (4)0.114 (5)0.002 (3)0.044 (4)0.003 (3)
C120.077 (4)0.060 (4)0.095 (4)0.017 (3)0.028 (3)0.005 (3)
C130.059 (3)0.078 (4)0.073 (4)0.015 (3)0.029 (3)0.005 (3)
C140.049 (3)0.052 (3)0.051 (3)0.002 (2)0.018 (2)0.001 (2)
C150.119 (4)0.057 (4)0.091 (4)0.011 (3)0.028 (4)0.000 (3)
C160.064 (3)0.054 (3)0.062 (3)0.000 (3)0.038 (3)0.001 (3)
C170.082 (4)0.053 (3)0.074 (4)0.000 (3)0.049 (3)0.001 (3)
C180.078 (3)0.054 (3)0.051 (3)0.007 (3)0.030 (3)0.000 (3)
C190.063 (3)0.067 (4)0.080 (4)0.018 (3)0.039 (3)0.000 (3)
C200.053 (3)0.064 (3)0.074 (3)0.005 (3)0.037 (3)0.003 (3)
C210.044 (3)0.053 (3)0.034 (3)0.007 (2)0.014 (2)0.001 (2)
C220.032 (2)0.057 (3)0.037 (2)0.003 (2)0.014 (2)0.004 (2)
C230.040 (2)0.050 (3)0.041 (3)0.008 (2)0.015 (2)0.005 (2)
C240.042 (3)0.050 (3)0.040 (3)0.005 (2)0.009 (2)0.002 (2)
C250.052 (3)0.058 (3)0.074 (4)0.001 (3)0.024 (3)0.003 (3)
C260.075 (4)0.047 (3)0.090 (4)0.004 (3)0.027 (3)0.006 (3)
C270.071 (4)0.055 (3)0.092 (4)0.019 (3)0.028 (3)0.001 (3)
C280.053 (3)0.061 (3)0.079 (4)0.012 (3)0.024 (3)0.004 (3)
C290.043 (3)0.062 (3)0.056 (3)0.001 (2)0.020 (2)0.001 (2)
C300.114 (4)0.062 (3)0.087 (4)0.023 (3)0.053 (3)0.007 (3)
Geometric parameters (Å, º) top
Cl1—C141.734 (4)C12—H120.9300
Cl2—C291.738 (4)C13—C141.399 (5)
S1—C71.717 (4)C13—H130.9300
S1—C81.727 (4)C15—H15A0.9600
S2—C221.723 (4)C15—H15B0.9600
S2—C231.723 (4)C15—H15C0.9600
N1—C81.304 (4)C16—C171.377 (5)
N1—N21.380 (4)C16—C211.390 (5)
N2—C71.286 (4)C16—H160.9300
N3—C221.307 (5)C17—C181.382 (5)
N3—N41.372 (4)C17—H170.9300
N4—C231.302 (4)C18—C191.386 (6)
C1—C61.375 (5)C18—C301.507 (5)
C1—C21.397 (6)C19—C201.371 (5)
C1—H10.9300C19—H190.9300
C2—C31.376 (6)C20—C211.390 (5)
C2—H20.9300C20—H200.9300
C3—C41.371 (6)C21—C221.476 (5)
C3—C151.509 (6)C23—C241.487 (5)
C4—C51.370 (6)C24—C291.398 (5)
C4—H40.9300C24—C251.398 (5)
C5—C61.390 (5)C25—C261.375 (5)
C5—H50.9300C25—H250.9300
C6—C71.472 (5)C26—C271.375 (5)
C8—C91.472 (5)C26—H260.9300
C9—C141.390 (5)C27—C281.370 (6)
C9—C101.402 (5)C27—H270.9300
C10—C111.376 (5)C28—C291.383 (5)
C10—H100.9300C28—H280.9300
C11—C121.366 (6)C30—H30A0.9600
C11—H110.9300C30—H30B0.9600
C12—C131.375 (6)C30—H30C0.9600
C7—S1—C887.9 (2)C3—C15—H15C109.5
C22—S2—C2387.7 (2)H15A—C15—H15C109.5
C8—N1—N2113.3 (3)H15B—C15—H15C109.5
C7—N2—N1112.6 (3)C17—C16—C21120.8 (4)
C22—N3—N4112.2 (3)C17—C16—H16119.6
C23—N4—N3113.7 (3)C21—C16—H16119.6
C6—C1—C2120.5 (4)C16—C17—C18121.8 (4)
C6—C1—H1119.8C16—C17—H17119.1
C2—C1—H1119.8C18—C17—H17119.1
C3—C2—C1121.7 (4)C17—C18—C19117.0 (4)
C3—C2—H2119.1C17—C18—C30122.8 (4)
C1—C2—H2119.1C19—C18—C30120.3 (4)
C4—C3—C2116.8 (5)C20—C19—C18122.0 (4)
C4—C3—C15122.0 (5)C20—C19—H19119.0
C2—C3—C15121.2 (5)C18—C19—H19119.0
C5—C4—C3122.7 (5)C19—C20—C21120.7 (4)
C5—C4—H4118.7C19—C20—H20119.6
C3—C4—H4118.7C21—C20—H20119.6
C4—C5—C6120.6 (4)C16—C21—C20117.7 (4)
C4—C5—H5119.7C16—C21—C22121.9 (4)
C6—C5—H5119.7C20—C21—C22120.4 (4)
C1—C6—C5117.8 (4)N3—C22—C21121.9 (3)
C1—C6—C7122.2 (4)N3—C22—S2113.5 (3)
C5—C6—C7120.0 (4)C21—C22—S2124.6 (3)
N2—C7—C6122.8 (4)N4—C23—C24119.6 (4)
N2—C7—S1113.9 (3)N4—C23—S2112.9 (3)
C6—C7—S1123.3 (3)C24—C23—S2127.6 (3)
N1—C8—C9119.4 (4)C29—C24—C25116.0 (4)
N1—C8—S1112.4 (3)C29—C24—C23126.6 (4)
C9—C8—S1128.3 (3)C25—C24—C23117.3 (4)
C14—C9—C10117.2 (4)C26—C25—C24121.9 (4)
C14—C9—C8125.5 (4)C26—C25—H25119.0
C10—C9—C8117.4 (4)C24—C25—H25119.0
C11—C10—C9121.4 (4)C25—C26—C27120.2 (4)
C11—C10—H10119.3C25—C26—H26119.9
C9—C10—H10119.3C27—C26—H26119.9
C12—C11—C10120.4 (5)C28—C27—C26119.9 (4)
C12—C11—H11119.8C28—C27—H27120.1
C10—C11—H11119.8C26—C27—H27120.1
C11—C12—C13120.1 (5)C27—C28—C29119.7 (4)
C11—C12—H12119.9C27—C28—H28120.1
C13—C12—H12119.9C29—C28—H28120.1
C12—C13—C14119.8 (4)C28—C29—C24122.2 (4)
C12—C13—H13120.1C28—C29—Cl2116.8 (3)
C14—C13—H13120.1C24—C29—Cl2120.9 (3)
C9—C14—C13121.1 (4)C18—C30—H30A109.5
C9—C14—Cl1122.2 (3)C18—C30—H30B109.5
C13—C14—Cl1116.7 (4)H30A—C30—H30B109.5
C3—C15—H15A109.5C18—C30—H30C109.5
C3—C15—H15B109.5H30A—C30—H30C109.5
H15A—C15—H15B109.5H30B—C30—H30C109.5
C8—N1—N2—C70.5 (5)C12—C13—C14—Cl1179.2 (4)
C22—N3—N4—C231.2 (5)C21—C16—C17—C180.5 (7)
C6—C1—C2—C30.0 (7)C16—C17—C18—C190.3 (6)
C1—C2—C3—C40.8 (7)C16—C17—C18—C30178.9 (4)
C1—C2—C3—C15178.6 (4)C17—C18—C19—C200.3 (7)
C2—C3—C4—C51.0 (7)C30—C18—C19—C20179.4 (4)
C15—C3—C4—C5178.4 (4)C18—C19—C20—C210.6 (7)
C3—C4—C5—C60.3 (7)C17—C16—C21—C200.3 (6)
C2—C1—C6—C50.7 (6)C17—C16—C21—C22178.4 (4)
C2—C1—C6—C7179.5 (4)C19—C20—C21—C160.3 (6)
C4—C5—C6—C10.5 (6)C19—C20—C21—C22177.8 (4)
C4—C5—C6—C7179.7 (4)N4—N3—C22—C21179.9 (3)
N1—N2—C7—C6179.4 (4)N4—N3—C22—S20.7 (5)
N1—N2—C7—S10.1 (5)C16—C21—C22—N3171.8 (4)
C1—C6—C7—N2177.3 (4)C20—C21—C22—N36.3 (6)
C5—C6—C7—N22.9 (6)C16—C21—C22—S29.1 (5)
C1—C6—C7—S12.0 (6)C20—C21—C22—S2172.8 (3)
C5—C6—C7—S1177.8 (3)C23—S2—C22—N30.1 (3)
C8—S1—C7—N20.4 (3)C23—S2—C22—C21179.3 (3)
C8—S1—C7—C6179.8 (3)N3—N4—C23—C24179.5 (3)
N2—N1—C8—C9179.2 (4)N3—N4—C23—S21.1 (4)
N2—N1—C8—S10.8 (5)C22—S2—C23—N40.6 (3)
C7—S1—C8—N10.7 (3)C22—S2—C23—C24180.0 (4)
C7—S1—C8—C9179.3 (4)N4—C23—C24—C29171.7 (4)
N1—C8—C9—C14177.1 (4)S2—C23—C24—C297.7 (6)
S1—C8—C9—C142.8 (6)N4—C23—C24—C257.6 (5)
N1—C8—C9—C103.2 (6)S2—C23—C24—C25173.1 (3)
S1—C8—C9—C10176.8 (3)C29—C24—C25—C261.3 (6)
C14—C9—C10—C111.3 (7)C23—C24—C25—C26178.0 (4)
C8—C9—C10—C11179.1 (4)C24—C25—C26—C270.9 (7)
C9—C10—C11—C120.9 (7)C25—C26—C27—C280.7 (7)
C10—C11—C12—C130.0 (7)C26—C27—C28—C291.0 (7)
C11—C12—C13—C140.4 (7)C27—C28—C29—C241.4 (7)
C10—C9—C14—C130.8 (6)C27—C28—C29—Cl2179.5 (3)
C8—C9—C14—C13179.5 (4)C25—C24—C29—C281.5 (6)
C10—C9—C14—Cl1180.0 (3)C23—C24—C29—C28177.7 (4)
C8—C9—C14—Cl10.4 (6)C25—C24—C29—Cl2179.4 (3)
C12—C13—C14—C90.0 (7)C23—C24—C29—Cl21.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···N4i0.932.533.388 (8)153
C28—H28···N1ii0.932.493.303 (7)146
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1, z.
 

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