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The title compound, C15H15N3S, was prepared by the reaction of acetophenone and hydrazine with phenyl­isothio­cyanate. In the mol­ecule, all bond lengths and angles are within normal ranges. The two phen­yl rings make a dihedral angle of 61.6 (2)°. The crystal packing is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019070/cv6531sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019070/cv6531Isup2.hkl
Contains datablock I

CCDC reference: 277242

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.054
  • wR factor = 0.169
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Alert level B PLAT414_ALERT_2_B Short Intra D-H..H-X H2B .. H8A .. 1.88 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-phenyl-1-(1-phenylethylidene)thiosemicarbazide top
Crystal data top
C15H15N3SZ = 2
Mr = 269.36F(000) = 284
Triclinic, P1Dx = 1.277 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9250 (12) ÅCell parameters from 25 reflections
b = 10.514 (2) Åθ = 4–26°
c = 11.567 (2) ŵ = 0.22 mm1
α = 103.54 (3)°T = 295 K
β = 91.10 (3)°Block, colourless
γ = 90.19 (3)°0.25 × 0.20 × 0.18 mm
V = 700.4 (2) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.032
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 1.8°
Graphite monochromatorh = 07
ω scansk = 1212
3302 measured reflectionsl = 1313
3014 independent reflections3 standard reflections every 100 reflections
1352 reflections with I > 2σ(I) intensity decay: none
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0732P)2]
where P = (Fo2 + 2Fc2)/3
3014 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
S10.46358 (16)0.10038 (10)0.64428 (9)0.0540 (4)
N10.0233 (5)0.1552 (3)0.6569 (2)0.0430 (7)
N20.1643 (5)0.0762 (3)0.6197 (3)0.0471 (8)
N30.0738 (5)0.0272 (3)0.7657 (3)0.0499 (8)
C10.2982 (7)0.4517 (3)0.6286 (4)0.0649 (12)
H1B0.19570.47990.57830.078*
C20.4770 (8)0.5318 (4)0.6770 (5)0.0770 (14)
H2A0.49440.61290.65900.092*
C30.6299 (7)0.4918 (4)0.7521 (4)0.0746 (14)
H3A0.75010.54600.78550.090*
C40.6037 (7)0.3718 (4)0.7773 (3)0.0687 (12)
H4A0.70650.34450.82810.082*
C50.4256 (6)0.2910 (4)0.7277 (3)0.0506 (10)
H5A0.41110.20910.74450.061*
C60.2675 (5)0.3305 (3)0.6530 (3)0.0403 (8)
C70.0696 (5)0.2451 (3)0.6032 (3)0.0406 (8)
C80.0639 (6)0.2717 (4)0.5001 (3)0.0551 (10)
H8A0.18500.20920.47950.083*
H8B0.03270.26470.43330.083*
H8C0.12480.35840.52170.083*
C90.2227 (5)0.0143 (3)0.6804 (3)0.0419 (9)
C100.0896 (6)0.1126 (3)0.8445 (3)0.0429 (9)
C110.0908 (6)0.1922 (4)0.8548 (3)0.0550 (10)
H11A0.21640.19290.80760.066*
C120.0853 (7)0.2709 (4)0.9351 (4)0.0645 (12)
H12A0.20700.32460.94160.077*
C130.0994 (7)0.2700 (4)1.0053 (3)0.0608 (11)
H13A0.10260.32221.06000.073*
C140.2794 (7)0.1913 (4)0.9939 (3)0.0628 (11)
H14A0.40590.19221.04010.075*
C150.2754 (6)0.1109 (4)0.9149 (3)0.0546 (10)
H15A0.39640.05640.90930.066*
H3B0.042 (6)0.022 (3)0.769 (3)0.053 (11)*
H2B0.244 (6)0.085 (4)0.569 (3)0.057 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0418 (5)0.0627 (7)0.0637 (7)0.0198 (5)0.0127 (5)0.0290 (5)
N10.0351 (16)0.0451 (17)0.0508 (18)0.0086 (13)0.0054 (14)0.0159 (14)
N20.0396 (18)0.055 (2)0.052 (2)0.0110 (15)0.0083 (16)0.0256 (17)
N30.0429 (18)0.058 (2)0.056 (2)0.0194 (16)0.0115 (15)0.0273 (16)
C10.056 (3)0.050 (2)0.094 (3)0.011 (2)0.017 (2)0.028 (2)
C20.069 (3)0.048 (3)0.114 (4)0.019 (2)0.004 (3)0.021 (3)
C30.058 (3)0.075 (3)0.075 (3)0.029 (2)0.001 (2)0.014 (3)
C40.055 (3)0.097 (3)0.056 (3)0.019 (2)0.012 (2)0.024 (2)
C50.047 (2)0.059 (2)0.050 (2)0.0109 (19)0.0064 (18)0.0231 (19)
C60.0368 (19)0.041 (2)0.044 (2)0.0054 (16)0.0007 (16)0.0126 (17)
C70.0363 (19)0.044 (2)0.044 (2)0.0011 (16)0.0020 (16)0.0167 (17)
C80.049 (2)0.063 (2)0.061 (2)0.0088 (19)0.008 (2)0.031 (2)
C90.038 (2)0.042 (2)0.046 (2)0.0045 (16)0.0026 (17)0.0134 (17)
C100.041 (2)0.049 (2)0.038 (2)0.0141 (17)0.0078 (16)0.0118 (17)
C110.041 (2)0.079 (3)0.052 (2)0.008 (2)0.0032 (18)0.028 (2)
C120.052 (2)0.085 (3)0.066 (3)0.001 (2)0.010 (2)0.039 (2)
C130.062 (3)0.079 (3)0.051 (2)0.014 (2)0.012 (2)0.035 (2)
C140.052 (2)0.095 (3)0.047 (2)0.009 (2)0.003 (2)0.028 (2)
C150.048 (2)0.068 (3)0.051 (2)0.0035 (19)0.003 (2)0.020 (2)
Geometric parameters (Å, º) top
S1—C91.680 (3)C5—H5A0.9300
N1—C71.279 (4)C6—C71.496 (4)
N1—N21.385 (4)C7—C81.499 (4)
N2—C91.356 (4)C8—H8A0.9600
N2—H2B0.77 (4)C8—H8B0.9600
N3—C91.343 (4)C8—H8C0.9600
N3—C101.425 (4)C10—C151.379 (5)
N3—H3B0.85 (3)C10—C111.381 (5)
C1—C21.377 (5)C11—C121.381 (5)
C1—C61.381 (4)C11—H11A0.9300
C1—H1B0.9300C12—C131.374 (5)
C2—C31.377 (6)C12—H12A0.9300
C2—H2A0.9300C13—C141.375 (5)
C3—C41.369 (5)C13—H13A0.9300
C3—H3A0.9300C14—C151.384 (5)
C4—C51.381 (5)C14—H14A0.9300
C4—H4A0.9300C15—H15A0.9300
C5—C61.392 (5)
C7—N1—N2118.9 (3)C7—C8—H8A109.5
C9—N2—N1119.4 (3)C7—C8—H8B109.5
C9—N2—H2B118 (3)H8A—C8—H8B109.5
N1—N2—H2B123 (3)C7—C8—H8C109.5
C9—N3—C10127.5 (3)H8A—C8—H8C109.5
C9—N3—H3B112 (2)H8B—C8—H8C109.5
C10—N3—H3B120 (2)N3—C9—N2114.6 (3)
C2—C1—C6121.6 (4)N3—C9—S1125.7 (3)
C2—C1—H1B119.2N2—C9—S1119.7 (3)
C6—C1—H1B119.2C15—C10—C11120.0 (3)
C1—C2—C3120.0 (4)C15—C10—N3121.0 (3)
C1—C2—H2A120.0C11—C10—N3118.8 (3)
C3—C2—H2A120.0C10—C11—C12120.1 (4)
C4—C3—C2119.6 (4)C10—C11—H11A119.9
C4—C3—H3A120.2C12—C11—H11A119.9
C2—C3—H3A120.2C13—C12—C11120.2 (4)
C3—C4—C5120.4 (4)C13—C12—H12A119.9
C3—C4—H4A119.8C11—C12—H12A119.9
C5—C4—H4A119.8C12—C13—C14119.4 (4)
C4—C5—C6120.8 (3)C12—C13—H13A120.3
C4—C5—H5A119.6C14—C13—H13A120.3
C6—C5—H5A119.6C13—C14—C15121.1 (4)
C1—C6—C5117.6 (3)C13—C14—H14A119.5
C1—C6—C7121.5 (3)C15—C14—H14A119.5
C5—C6—C7120.8 (3)C10—C15—C14119.1 (4)
N1—C7—C6115.4 (3)C10—C15—H15A120.4
N1—C7—C8124.7 (3)C14—C15—H15A120.4
C6—C7—C8119.8 (3)
C7—N1—N2—C9176.1 (3)C10—N3—C9—N2179.3 (3)
C6—C1—C2—C30.3 (7)C10—N3—C9—S11.6 (6)
C1—C2—C3—C40.5 (7)N1—N2—C9—N36.8 (5)
C2—C3—C4—C50.1 (6)N1—N2—C9—S1174.1 (2)
C3—C4—C5—C61.1 (6)C9—N3—C10—C1554.9 (5)
C2—C1—C6—C50.6 (6)C9—N3—C10—C11128.9 (4)
C2—C1—C6—C7178.2 (3)C15—C10—C11—C120.4 (6)
C4—C5—C6—C11.3 (5)N3—C10—C11—C12176.6 (3)
C4—C5—C6—C7177.6 (3)C10—C11—C12—C130.2 (6)
N2—N1—C7—C6176.9 (3)C11—C12—C13—C140.7 (6)
N2—N1—C7—C80.8 (5)C12—C13—C14—C151.5 (6)
C1—C6—C7—N1160.9 (3)C11—C10—C15—C141.1 (5)
C5—C6—C7—N117.9 (5)N3—C10—C15—C14177.2 (3)
C1—C6—C7—C816.9 (5)C13—C14—C15—C101.6 (6)
C5—C6—C7—C8164.3 (3)
 

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