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The title compound, C15H14N2S, was prepared by the reaction of aniline with isothiocanatobenzene and 1,2-dibromo­ethane at room temperature. The thiazolidne plane forms dihedral angles with the phenyl rings of 65.46 and 42.12°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051324/sj2164sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051324/sj2164Isup2.hkl
Contains datablock I

CCDC reference: 633999

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.077
  • wR factor = 0.152
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT414_ALERT_2_B Short Intra D-H..H-X H1A .. H11A .. 1.89 Ang.
Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 200 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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, 1997); 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).

N,3-Diphenylthiazolidin-5-amine top
Crystal data top
C15H15N2SF(000) = 540
Mr = 255.35Dx = 1.295 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.742 (2) Åθ = 4–14°
b = 11.557 (2) ŵ = 0.23 mm1
c = 10.568 (2) ÅT = 293 K
β = 93.43 (3)°Block, colourless
V = 1309.6 (4) Å30.23 × 0.20 × 0.18 mm
Z = 4
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.025
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.9°
Graphite monochromatorh = 1212
ω scansk = 1213
5203 measured reflectionsl = 1112
2282 independent reflections3 standard reflections every 100 reflections
2170 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)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.33 w = 1/[σ2(Fo2) + (0.0273P)2 + 1.3498P]
where P = (Fo2 + 2Fc2)/3
2282 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.49 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
S10.72556 (9)0.07228 (9)0.23730 (10)0.0508 (3)
N10.6519 (3)0.2853 (3)0.3094 (3)0.0451 (8)
H1A0.60090.33090.34440.054*
N20.5261 (3)0.1262 (2)0.3516 (3)0.0405 (7)
C10.7829 (4)0.3185 (3)0.1326 (4)0.0503 (10)
H1B0.72650.27850.07860.060*
C20.8893 (4)0.3650 (4)0.0857 (4)0.0629 (12)
H2A0.90440.35570.00050.075*
C30.9723 (4)0.4246 (4)0.1637 (5)0.0690 (13)
H3A1.04460.45450.13210.083*
C40.9488 (4)0.4405 (4)0.2892 (5)0.0651 (12)
H4A1.00440.48240.34210.078*
C50.8425 (4)0.3938 (4)0.3365 (4)0.0543 (10)
H5A0.82670.40500.42120.065*
C60.7595 (3)0.3309 (3)0.2590 (4)0.0416 (8)
C70.6291 (3)0.1791 (3)0.3040 (3)0.0371 (8)
C80.5122 (3)0.0034 (3)0.3187 (3)0.0443 (9)
H8A0.46540.00560.23790.053*
H8B0.46880.03750.38310.053*
C90.6429 (4)0.0426 (3)0.3114 (4)0.0514 (10)
H9A0.64320.11260.26080.062*
H9B0.68000.05920.39540.062*
C100.4230 (3)0.1893 (3)0.3947 (3)0.0374 (8)
C110.4408 (4)0.2842 (3)0.4728 (3)0.0472 (9)
H11A0.52110.30920.49670.057*
C120.3386 (4)0.3421 (4)0.5154 (4)0.0589 (11)
H12A0.35090.40620.56780.071*
C130.2194 (4)0.3064 (4)0.4815 (4)0.0627 (12)
H13A0.15130.34550.51120.075*
C140.2020 (4)0.2128 (4)0.4036 (4)0.0604 (11)
H14A0.12150.18870.37920.072*
C150.3027 (3)0.1537 (4)0.3610 (4)0.0487 (10)
H15A0.28960.08930.30900.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0531 (6)0.0423 (6)0.0587 (6)0.0112 (4)0.0187 (5)0.0037 (5)
N10.0410 (17)0.0381 (18)0.057 (2)0.0013 (14)0.0136 (15)0.0050 (15)
N20.0399 (17)0.0329 (16)0.0496 (17)0.0020 (13)0.0103 (14)0.0008 (14)
C10.046 (2)0.051 (2)0.054 (2)0.0104 (18)0.0010 (18)0.0005 (19)
C20.058 (3)0.072 (3)0.061 (3)0.012 (2)0.017 (2)0.008 (2)
C30.044 (2)0.078 (3)0.085 (3)0.011 (2)0.010 (2)0.016 (3)
C40.049 (3)0.066 (3)0.079 (3)0.018 (2)0.009 (2)0.006 (2)
C50.055 (3)0.055 (3)0.052 (2)0.004 (2)0.0019 (19)0.002 (2)
C60.0366 (19)0.0361 (19)0.052 (2)0.0004 (15)0.0039 (16)0.0049 (17)
C70.0388 (19)0.038 (2)0.0351 (18)0.0035 (15)0.0038 (15)0.0019 (15)
C80.053 (2)0.034 (2)0.046 (2)0.0035 (16)0.0020 (17)0.0023 (16)
C90.065 (3)0.038 (2)0.051 (2)0.0065 (18)0.010 (2)0.0060 (17)
C100.0399 (19)0.040 (2)0.0330 (17)0.0000 (15)0.0069 (15)0.0063 (15)
C110.043 (2)0.057 (2)0.042 (2)0.0017 (18)0.0041 (17)0.0035 (18)
C120.061 (3)0.070 (3)0.046 (2)0.012 (2)0.008 (2)0.011 (2)
C130.052 (3)0.075 (3)0.063 (3)0.017 (2)0.017 (2)0.002 (2)
C140.041 (2)0.071 (3)0.070 (3)0.001 (2)0.010 (2)0.005 (2)
C150.047 (2)0.050 (2)0.049 (2)0.0033 (18)0.0059 (18)0.0017 (18)
Geometric parameters (Å, º) top
S1—C71.784 (3)C5—H5A0.9300
S1—C91.802 (4)C8—C91.507 (5)
N1—C71.252 (4)C8—H8A0.9700
N1—C61.404 (4)C8—H8B0.9700
N1—H1A0.8600C9—H9A0.9700
N2—C71.385 (4)C9—H9B0.9700
N2—C101.424 (4)C10—C111.379 (5)
N2—C81.467 (4)C10—C151.383 (5)
C1—C61.382 (5)C11—C121.383 (5)
C1—C21.382 (5)C11—H11A0.9300
C1—H1B0.9300C12—C131.373 (6)
C2—C31.364 (6)C12—H12A0.9300
C2—H2A0.9300C13—C141.366 (6)
C3—C41.377 (6)C13—H13A0.9300
C3—H3A0.9300C14—C151.377 (5)
C4—C51.383 (6)C14—H14A0.9300
C4—H4A0.9300C15—H15A0.9300
C5—C61.380 (5)
C7—S1—C991.42 (17)N2—C8—H8A110.6
C7—N1—C6121.0 (3)C9—C8—H8A110.6
C7—N1—H1A119.5N2—C8—H8B110.6
C6—N1—H1A119.5C9—C8—H8B110.6
C7—N2—C10122.9 (3)H8A—C8—H8B108.7
C7—N2—C8114.4 (3)C8—C9—S1104.3 (2)
C10—N2—C8120.1 (3)C8—C9—H9A110.9
C6—C1—C2120.6 (4)S1—C9—H9A110.9
C6—C1—H1B119.7C8—C9—H9B110.9
C2—C1—H1B119.7S1—C9—H9B110.9
C3—C2—C1120.3 (4)H9A—C9—H9B108.9
C3—C2—H2A119.9C11—C10—C15119.0 (3)
C1—C2—H2A119.9C11—C10—N2121.1 (3)
C2—C3—C4119.9 (4)C15—C10—N2119.8 (3)
C2—C3—H3A120.0C10—C11—C12119.7 (4)
C4—C3—H3A120.0C10—C11—H11A120.2
C3—C4—C5119.9 (4)C12—C11—H11A120.2
C3—C4—H4A120.0C13—C12—C11121.1 (4)
C5—C4—H4A120.0C13—C12—H12A119.5
C6—C5—C4120.6 (4)C11—C12—H12A119.5
C6—C5—H5A119.7C14—C13—C12119.1 (4)
C4—C5—H5A119.7C14—C13—H13A120.4
C5—C6—C1118.7 (3)C12—C13—H13A120.4
C5—C6—N1119.4 (3)C13—C14—C15120.6 (4)
C1—C6—N1121.9 (3)C13—C14—H14A119.7
N1—C7—N2125.1 (3)C15—C14—H14A119.7
N1—C7—S1125.4 (3)C14—C15—C10120.5 (4)
N2—C7—S1109.5 (3)C14—C15—H15A119.8
N2—C8—C9105.7 (3)C10—C15—H15A119.8
C6—C1—C2—C30.4 (7)C9—S1—C7—N213.4 (3)
C1—C2—C3—C41.3 (7)C7—N2—C8—C932.2 (4)
C2—C3—C4—C51.3 (7)C10—N2—C8—C9165.4 (3)
C3—C4—C5—C60.3 (7)N2—C8—C9—S139.2 (3)
C4—C5—C6—C12.0 (6)C7—S1—C9—C830.4 (3)
C4—C5—C6—N1179.6 (4)C7—N2—C10—C1145.9 (5)
C2—C1—C6—C52.1 (6)C8—N2—C10—C11153.2 (3)
C2—C1—C6—N1179.6 (4)C7—N2—C10—C15135.8 (4)
C7—N1—C6—C5123.1 (4)C8—N2—C10—C1525.1 (5)
C7—N1—C6—C159.4 (5)C15—C10—C11—C120.2 (5)
C6—N1—C7—N2179.6 (3)N2—C10—C11—C12178.5 (3)
C6—N1—C7—S11.0 (5)C10—C11—C12—C130.2 (6)
C10—N2—C7—N110.4 (6)C11—C12—C13—C140.5 (7)
C8—N2—C7—N1172.3 (3)C12—C13—C14—C150.9 (7)
C10—N2—C7—S1170.9 (3)C13—C14—C15—C101.0 (6)
C8—N2—C7—S19.0 (4)C11—C10—C15—C140.6 (6)
C9—S1—C7—N1165.3 (3)N2—C10—C15—C14178.9 (3)
 

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