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The title compound, C17H15NOS, crystallizes in space group P\overline 1 with two independent mol­ecules in the asymmetric unit. The dihedral angles between the two benzene rings and the heterocyclic five-membered mean ring in the two independent mol­ecules are different: 35.62 (7) and 58.80 (7)° in one mol­ecule and 14.80 (12) and 60.09 (6)° in the other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002102/rn6038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002102/rn6038Isup2.hkl
Contains datablock I

CCDC reference: 264085

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.095
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(Z)-1-phenyl-2-(3-phenylthiazolidin-2-ylidene)ethanone top
Crystal data top
C17H15NOSZ = 4
Mr = 281.37F(000) = 592
Triclinic, P1Dx = 1.304 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5998 (12) ÅCell parameters from 2755 reflections
b = 10.8872 (13) Åθ = 2.4–24.8°
c = 14.4903 (18) ŵ = 0.22 mm1
α = 79.303 (2)°T = 293 K
β = 76.243 (2)°Prism, colorless
γ = 80.467 (2)°0.52 × 0.38 × 0.19 mm
V = 1433.7 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
5001 independent reflections
Radiation source: fine-focus sealed tube3811 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.871, Tmax = 0.959k = 1212
7858 measured reflectionsl = 1017
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.042P)2 + 0.2564P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5001 reflectionsΔρmax = 0.20 e Å3
362 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0143 (12)
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
S10.68744 (5)0.64203 (4)0.36344 (4)0.06226 (16)
S20.89042 (6)0.78740 (5)0.06898 (4)0.06850 (17)
N10.49204 (15)0.77544 (12)0.28037 (10)0.0517 (3)
N21.05010 (15)0.66549 (13)0.18362 (10)0.0524 (4)
O10.81155 (14)0.81511 (12)0.42354 (10)0.0682 (4)
O20.75642 (15)0.60975 (13)0.02826 (10)0.0756 (4)
C10.5677 (2)0.55992 (17)0.32419 (17)0.0724 (6)
H1A0.62080.48660.29680.087*
H1B0.49160.53270.37780.087*
C20.5054 (2)0.65275 (17)0.24992 (16)0.0677 (5)
H2A0.56900.65150.18700.081*
H2B0.41160.63350.24700.081*
C30.59426 (17)0.78811 (15)0.32763 (12)0.0484 (4)
C40.62305 (18)0.89940 (16)0.34451 (12)0.0517 (4)
H40.57080.97370.32110.062*
C50.72900 (18)0.90732 (16)0.39611 (12)0.0508 (4)
C60.74243 (18)1.03513 (16)0.41560 (12)0.0515 (4)
C70.6259 (2)1.12843 (17)0.42766 (13)0.0580 (4)
H70.53571.11330.42260.070*
C80.6422 (2)1.24334 (19)0.44708 (15)0.0719 (5)
H80.56271.30500.45580.086*
C90.7742 (3)1.2678 (2)0.45363 (17)0.0847 (7)
H90.78481.34620.46590.102*
C100.8909 (3)1.1766 (2)0.44216 (18)0.0889 (7)
H100.98091.19310.44660.107*
C110.8753 (2)1.0603 (2)0.42404 (15)0.0714 (6)
H110.95470.99820.41740.086*
C120.40616 (17)0.88070 (15)0.23832 (12)0.0470 (4)
C130.41610 (19)0.90281 (17)0.14032 (13)0.0568 (4)
H130.47880.84910.10160.068*
C140.3329 (2)1.00477 (19)0.09988 (14)0.0660 (5)
H140.33911.01900.03380.079*
C150.2413 (2)1.08516 (19)0.15617 (15)0.0673 (5)
H150.18681.15480.12840.081*
C160.2305 (2)1.06232 (18)0.25365 (15)0.0653 (5)
H160.16801.11650.29210.078*
C170.31150 (19)0.95961 (16)0.29539 (13)0.0561 (4)
H170.30220.94380.36170.067*
C181.0140 (3)0.87149 (19)0.10189 (17)0.0814 (6)
H18A1.10090.87760.05170.098*
H18B0.96910.95590.11210.098*
C191.0491 (2)0.79721 (17)0.19230 (15)0.0685 (5)
H19A1.14290.81160.19930.082*
H19B0.97670.82030.24760.082*
C200.95612 (18)0.64621 (16)0.13268 (12)0.0510 (4)
C210.91298 (19)0.53291 (17)0.13291 (12)0.0564 (4)
H210.95270.46150.16870.068*
C220.80977 (19)0.51977 (18)0.08067 (13)0.0579 (4)
C230.75626 (19)0.39420 (18)0.09455 (12)0.0572 (5)
C240.8103 (2)0.2865 (2)0.14824 (15)0.0732 (6)
H240.88770.28860.17590.088*
C250.7511 (3)0.1761 (2)0.16148 (17)0.0862 (7)
H250.78840.10420.19810.103*
C260.6372 (3)0.1719 (3)0.12072 (17)0.0885 (7)
H260.59700.09730.12980.106*
C270.5829 (3)0.2769 (3)0.06700 (17)0.0889 (7)
H270.50580.27430.03920.107*
C280.6422 (2)0.3870 (2)0.05380 (15)0.0752 (6)
H280.60480.45810.01660.090*
C291.11743 (17)0.56708 (15)0.24458 (11)0.0470 (4)
C301.09247 (18)0.57068 (17)0.34153 (12)0.0564 (4)
H301.03060.63640.36800.068*
C311.1603 (2)0.47559 (19)0.39923 (13)0.0642 (5)
H311.14320.47740.46490.077*
C321.2520 (2)0.37908 (18)0.36106 (15)0.0654 (5)
H321.29660.31530.40060.078*
C331.2780 (2)0.37655 (18)0.26433 (15)0.0656 (5)
H331.34150.31150.23800.079*
C341.2105 (2)0.47022 (17)0.20566 (13)0.0579 (5)
H341.22770.46790.14000.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0589 (3)0.0521 (3)0.0747 (3)0.0012 (2)0.0234 (2)0.0024 (2)
S20.0714 (3)0.0673 (3)0.0681 (3)0.0086 (2)0.0335 (3)0.0104 (2)
N10.0515 (8)0.0455 (8)0.0625 (9)0.0052 (6)0.0205 (7)0.0098 (7)
N20.0584 (8)0.0513 (8)0.0525 (8)0.0116 (7)0.0240 (7)0.0010 (6)
O10.0675 (8)0.0618 (8)0.0819 (9)0.0042 (7)0.0378 (7)0.0103 (7)
O20.0821 (9)0.0791 (9)0.0767 (9)0.0112 (7)0.0468 (8)0.0004 (7)
C10.0706 (12)0.0485 (11)0.0991 (16)0.0053 (9)0.0227 (11)0.0095 (10)
C20.0673 (12)0.0531 (11)0.0928 (15)0.0069 (9)0.0309 (11)0.0196 (10)
C30.0441 (9)0.0513 (10)0.0491 (9)0.0063 (7)0.0124 (7)0.0024 (8)
C40.0528 (10)0.0483 (9)0.0566 (10)0.0070 (8)0.0211 (8)0.0021 (8)
C50.0485 (9)0.0561 (10)0.0487 (10)0.0050 (8)0.0154 (8)0.0049 (8)
C60.0528 (10)0.0574 (10)0.0466 (9)0.0080 (8)0.0155 (8)0.0067 (8)
C70.0588 (11)0.0589 (11)0.0574 (11)0.0081 (9)0.0173 (9)0.0047 (9)
C80.0828 (14)0.0596 (12)0.0735 (14)0.0030 (10)0.0195 (11)0.0119 (10)
C90.1057 (18)0.0651 (13)0.0926 (17)0.0224 (13)0.0245 (14)0.0209 (12)
C100.0776 (15)0.0927 (17)0.114 (2)0.0283 (13)0.0310 (14)0.0315 (15)
C110.0582 (11)0.0788 (14)0.0874 (15)0.0093 (10)0.0257 (11)0.0247 (11)
C120.0458 (9)0.0483 (9)0.0513 (10)0.0128 (7)0.0170 (8)0.0043 (8)
C130.0574 (10)0.0635 (11)0.0531 (11)0.0150 (9)0.0137 (8)0.0092 (9)
C140.0729 (13)0.0760 (13)0.0543 (11)0.0212 (11)0.0264 (10)0.0039 (10)
C150.0678 (12)0.0629 (12)0.0755 (14)0.0112 (10)0.0358 (11)0.0074 (10)
C160.0610 (11)0.0589 (11)0.0758 (14)0.0019 (9)0.0190 (10)0.0125 (10)
C170.0597 (10)0.0588 (11)0.0510 (10)0.0047 (9)0.0172 (9)0.0071 (8)
C180.0921 (15)0.0613 (12)0.0953 (16)0.0158 (11)0.0416 (13)0.0099 (11)
C190.0801 (13)0.0550 (11)0.0778 (13)0.0203 (10)0.0324 (11)0.0019 (10)
C200.0500 (9)0.0614 (11)0.0421 (9)0.0079 (8)0.0151 (8)0.0019 (8)
C210.0602 (11)0.0607 (11)0.0540 (10)0.0098 (9)0.0254 (9)0.0040 (8)
C220.0576 (10)0.0711 (12)0.0501 (10)0.0095 (9)0.0196 (9)0.0107 (9)
C230.0576 (10)0.0747 (12)0.0452 (10)0.0149 (9)0.0130 (8)0.0156 (9)
C240.0788 (14)0.0743 (14)0.0767 (14)0.0178 (11)0.0287 (11)0.0147 (11)
C250.1076 (18)0.0743 (14)0.0817 (16)0.0241 (13)0.0226 (14)0.0107 (12)
C260.1062 (18)0.0992 (18)0.0709 (15)0.0523 (15)0.0027 (13)0.0263 (14)
C270.0863 (16)0.124 (2)0.0721 (15)0.0495 (16)0.0197 (13)0.0191 (15)
C280.0727 (13)0.0979 (16)0.0659 (13)0.0275 (12)0.0268 (11)0.0095 (11)
C290.0463 (9)0.0524 (9)0.0474 (9)0.0140 (8)0.0193 (7)0.0016 (8)
C300.0526 (10)0.0670 (11)0.0518 (11)0.0032 (9)0.0179 (8)0.0096 (9)
C310.0648 (11)0.0842 (14)0.0461 (10)0.0105 (11)0.0214 (9)0.0028 (10)
C320.0670 (12)0.0617 (12)0.0703 (13)0.0085 (10)0.0321 (10)0.0053 (10)
C330.0698 (12)0.0549 (11)0.0743 (14)0.0013 (9)0.0219 (10)0.0128 (10)
C340.0677 (11)0.0604 (11)0.0491 (10)0.0095 (9)0.0186 (9)0.0080 (9)
Geometric parameters (Å, º) top
S1—C31.7442 (16)C14—H140.9300
S1—C11.813 (2)C15—C161.370 (3)
S2—C201.7441 (17)C15—H150.9300
S2—C181.807 (2)C16—C171.380 (2)
N1—C31.360 (2)C16—H160.9300
N1—C121.425 (2)C17—H170.9300
N1—C21.460 (2)C18—C191.487 (3)
N2—C201.356 (2)C18—H18A0.9700
N2—C291.427 (2)C18—H18B0.9700
N2—C191.461 (2)C19—H19A0.9700
O1—C51.2378 (19)C19—H19B0.9700
O2—C221.241 (2)C20—C211.364 (2)
C1—C21.496 (3)C21—C221.421 (2)
C1—H1A0.9700C21—H210.9300
C1—H1B0.9700C22—C231.501 (3)
C2—H2A0.9700C23—C241.378 (3)
C2—H2B0.9700C23—C281.381 (2)
C3—C41.363 (2)C24—C251.376 (3)
C4—C51.420 (2)C24—H240.9300
C4—H40.9300C25—C261.372 (3)
C5—C61.502 (2)C25—H250.9300
C6—C71.382 (2)C26—C271.360 (3)
C6—C111.386 (2)C26—H260.9300
C7—C81.373 (3)C27—C281.372 (3)
C7—H70.9300C27—H270.9300
C8—C91.366 (3)C28—H280.9300
C8—H80.9300C29—C301.375 (2)
C9—C101.368 (3)C29—C341.377 (2)
C9—H90.9300C30—C311.382 (2)
C10—C111.377 (3)C30—H300.9300
C10—H100.9300C31—C321.365 (3)
C11—H110.9300C31—H310.9300
C12—C171.377 (2)C32—C331.369 (3)
C12—C131.378 (2)C32—H320.9300
C13—C141.379 (2)C33—C341.380 (2)
C13—H130.9300C33—H330.9300
C14—C151.369 (3)C34—H340.9300
C3—S1—C191.58 (8)C17—C16—H16119.7
C20—S2—C1891.32 (8)C12—C17—C16119.68 (17)
C3—N1—C12122.70 (13)C12—C17—H17120.2
C3—N1—C2114.95 (14)C16—C17—H17120.2
C12—N1—C2119.87 (14)C19—C18—S2105.88 (13)
C20—N2—C29123.32 (14)C19—C18—H18A110.6
C20—N2—C19114.62 (14)S2—C18—H18A110.6
C29—N2—C19120.21 (14)C19—C18—H18B110.6
C2—C1—S1105.81 (13)S2—C18—H18B110.6
C2—C1—H1A110.6H18A—C18—H18B108.7
S1—C1—H1A110.6N2—C19—C18105.49 (16)
C2—C1—H1B110.6N2—C19—H19A110.6
S1—C1—H1B110.6C18—C19—H19A110.6
H1A—C1—H1B108.7N2—C19—H19B110.6
N1—C2—C1105.52 (16)C18—C19—H19B110.6
N1—C2—H2A110.6H19A—C19—H19B108.8
C1—C2—H2A110.6N2—C20—C21125.33 (16)
N1—C2—H2B110.6N2—C20—S2111.17 (13)
C1—C2—H2B110.6C21—C20—S2123.47 (13)
H2A—C2—H2B108.8C20—C21—C22122.58 (17)
N1—C3—C4125.31 (15)C20—C21—H21118.7
N1—C3—S1111.09 (12)C22—C21—H21118.7
C4—C3—S1123.60 (13)O2—C22—C21122.47 (17)
C3—C4—C5123.11 (16)O2—C22—C23118.83 (16)
C3—C4—H4118.4C21—C22—C23118.58 (16)
C5—C4—H4118.4C24—C23—C28117.77 (19)
O1—C5—C4123.23 (16)C24—C23—C22124.21 (16)
O1—C5—C6119.17 (15)C28—C23—C22117.97 (18)
C4—C5—C6117.59 (15)C25—C24—C23120.9 (2)
C7—C6—C11118.40 (17)C25—C24—H24119.5
C7—C6—C5122.37 (15)C23—C24—H24119.5
C11—C6—C5119.22 (16)C26—C25—C24120.0 (2)
C8—C7—C6120.58 (18)C26—C25—H25120.0
C8—C7—H7119.7C24—C25—H25120.0
C6—C7—H7119.7C27—C26—C25119.9 (2)
C9—C8—C7120.5 (2)C27—C26—H26120.1
C9—C8—H8119.8C25—C26—H26120.1
C7—C8—H8119.8C26—C27—C28120.0 (2)
C8—C9—C10119.8 (2)C26—C27—H27120.0
C8—C9—H9120.1C28—C27—H27120.0
C10—C9—H9120.1C27—C28—C23121.4 (2)
C9—C10—C11120.1 (2)C27—C28—H28119.3
C9—C10—H10119.9C23—C28—H28119.3
C11—C10—H10119.9C30—C29—C34120.07 (15)
C10—C11—C6120.5 (2)C30—C29—N2120.08 (16)
C10—C11—H11119.7C34—C29—N2119.83 (15)
C6—C11—H11119.7C29—C30—C31119.29 (17)
C17—C12—C13119.72 (16)C29—C30—H30120.4
C17—C12—N1120.24 (15)C31—C30—H30120.4
C13—C12—N1120.03 (16)C32—C31—C30120.84 (18)
C12—C13—C14119.87 (18)C32—C31—H31119.6
C12—C13—H13120.1C30—C31—H31119.6
C14—C13—H13120.1C31—C32—C33119.75 (18)
C15—C14—C13120.54 (18)C31—C32—H32120.1
C15—C14—H14119.7C33—C32—H32120.1
C13—C14—H14119.7C32—C33—C34120.23 (19)
C14—C15—C16119.50 (18)C32—C33—H33119.9
C14—C15—H15120.2C34—C33—H33119.9
C16—C15—H15120.2C29—C34—C33119.81 (17)
C15—C16—C17120.66 (19)C29—C34—H34120.1
C15—C16—H16119.7C33—C34—H34120.1
C3—S1—C1—C223.58 (15)C20—S2—C18—C1924.48 (17)
C3—N1—C2—C131.8 (2)C20—N2—C19—C1832.1 (2)
C12—N1—C2—C1165.56 (15)C29—N2—C19—C18162.91 (16)
S1—C1—C2—N133.59 (19)S2—C18—C19—N234.5 (2)
C12—N1—C3—C43.1 (3)C29—N2—C20—C210.4 (3)
C2—N1—C3—C4165.15 (17)C19—N2—C20—C21164.09 (17)
C12—N1—C3—S1176.16 (12)C29—N2—C20—S2178.15 (12)
C2—N1—C3—S114.10 (19)C19—N2—C20—S213.65 (19)
C1—S1—C3—N16.36 (14)C18—S2—C20—N27.03 (15)
C1—S1—C3—C4174.38 (16)C18—S2—C20—C21175.18 (17)
N1—C3—C4—C5178.60 (16)N2—C20—C21—C22177.54 (17)
S1—C3—C4—C52.2 (2)S2—C20—C21—C220.1 (3)
C3—C4—C5—O15.8 (3)C20—C21—C22—O23.0 (3)
C3—C4—C5—C6175.76 (15)C20—C21—C22—C23172.91 (16)
O1—C5—C6—C7150.82 (17)O2—C22—C23—C24177.73 (19)
C4—C5—C6—C730.7 (2)C21—C22—C23—C246.2 (3)
O1—C5—C6—C1127.7 (2)O2—C22—C23—C284.7 (3)
C4—C5—C6—C11150.83 (17)C21—C22—C23—C28171.38 (17)
C11—C6—C7—C80.3 (3)C28—C23—C24—C250.7 (3)
C5—C6—C7—C8178.83 (16)C22—C23—C24—C25176.90 (19)
C6—C7—C8—C90.8 (3)C23—C24—C25—C260.2 (3)
C7—C8—C9—C101.0 (3)C24—C25—C26—C270.2 (4)
C8—C9—C10—C110.0 (4)C25—C26—C27—C280.1 (4)
C9—C10—C11—C61.1 (4)C26—C27—C28—C230.4 (4)
C7—C6—C11—C101.2 (3)C24—C23—C28—C270.8 (3)
C5—C6—C11—C10179.82 (19)C22—C23—C28—C27177.0 (2)
C3—N1—C12—C1764.0 (2)C20—N2—C29—C30117.98 (19)
C2—N1—C12—C17134.79 (17)C19—N2—C29—C3045.7 (2)
C3—N1—C12—C13116.95 (18)C20—N2—C29—C3463.7 (2)
C2—N1—C12—C1344.3 (2)C19—N2—C29—C34132.60 (18)
C17—C12—C13—C141.0 (2)C34—C29—C30—C310.7 (3)
N1—C12—C13—C14179.97 (15)N2—C29—C30—C31179.03 (15)
C12—C13—C14—C150.6 (3)C29—C30—C31—C320.4 (3)
C13—C14—C15—C161.3 (3)C30—C31—C32—C330.4 (3)
C14—C15—C16—C170.3 (3)C31—C32—C33—C340.9 (3)
C13—C12—C17—C161.9 (2)C30—C29—C34—C330.3 (3)
N1—C12—C17—C16179.03 (15)N2—C29—C34—C33178.56 (15)
C15—C16—C17—C121.3 (3)C32—C33—C34—C290.5 (3)
 

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