(Z)-2-[2-(Cyano­imino)-1,3-thia­zolidin-1-yl]-1,3-diphenyl­prop-2-en-1-one

In the title compound, C₁₉H₁₅N₃OS, the 2-(cyano­imino)thia­zolidine unit is approximately planar and makes dihedral angles of 63.74 (13) and 68.56 (15)° with the plane of the benzoyl C atoms and the benzylidene phenyl ring, respectively. In the crystal structure, a weak inter­molecular C—H...O inter­action is observed.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.044
• wR factor = 0.108
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C15     ..       5.39 su
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               2864
           Count of symmetry unique reflns         1575
           Completeness (_total/calc)            181.84%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1289
           Fraction of Friedel pairs measured     0.818
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         19

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

Thiazolidine derivatives are reported to possess various biological activities and physiological activities, such as antihypertensive, vasodilator, antiulcer, insecticidal and herbicidal activities (Shiokawa et al., 1990; Ezer et al., 1984; Ogawa, 2000; Müller et al., 2002; Schmuck et al., 2003). They are becoming more and more important in the development of medicines and agriculture. (Honda et al., 2006; Yoneda et al., 2001; Klein, 2001; Oliver et al., 2005). In order to investigate novel biological compounds containing the 2-cyanoiminothiazolidine group, we designed and synthesized the title compound, (I).

Figure 1 shows the molecular structure of (I), which contains three planar rings: the phenyl ring (p1: C1—C6), the 1,3-thiazolidine ring (p2: S1/C18/N1/C16/C17), and the other phenyl ring (p3: C10—C15). The dihedral angles between p1 and p2, and between p3 and p2 are 64.9 (2) and 67.73 (18)°, respectively. The molecules are linked by intermolecular C—H···O hydrogen bonds (Fig. 2).

Related literature

For related literature, see: Ezer et al. (1984); Honda et al. (2006); Klein (2001); Liu et al. (2006); Müller et al. (2002); Ogawa (2000); Oliver et al. (2005); Schmuck et al. (2003); Shiokawa et al. (1990); Yoneda et al. (2001).

S2. Experimental

To a stirred solution of 3-[(2-oxo-2-phenylethyl)thiazolidin-2-ylideneamino] formonitrile (2.45 g, 10 mmol; Liu et al., 2006), benzaldehyde (1.27 g, 12 mmol) and anhydrous toluene (30 ml) were added a few drops of piperidine at room temperature under nitrogen. The mixture was heated to reflux for 5 h. The solvent was evaporated under reduced pressure and the residue was then purified by column chromatography on silica gel (200–300 mesh), with petroleum ether/ethyl acetate (4:1 v/v) as eluent. The resulting yellow solid was recrystallized from petroleum ether/ethyl acetate (2:3 v/v) to give yellow crystals (yield 76%).

S3. Refinement

The displacement parameters of atoms C12, C13 and C14 were restrained to behave approximately isotropic. The phenyl ring of C10—C15 was constrained as a hexagon with the C—C bonds of 1.39 Å. H atoms were placed in calculated positions (C—H = 0.93 or 0.97 Å) and were refined as riding, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound. Dashed lines indicate C—H···O hydrogen-bond interactions.

(Z)-2-[2-(Cyanoimino)-1,3-thiazolidin-1-yl]-1,3-diphenylprop-2-en-1-one

Crystal data

C19H15N3OS	F(000) = 348
Mr = 333.40	Dx = 1.324 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1300 reflections
a = 9.927 (4) Å	θ = 3.2–22.7°
b = 8.389 (4) Å	µ = 0.20 mm^−1
c = 10.883 (5) Å	T = 294 K
β = 112.660 (8)°	Monoclinic, yellow
V = 836.3 (7) Å^3	0.20 × 0.18 × 0.12 mm
Z = 2

Data collection

Bruker SMART 1000 diffractometer	2864 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
Tmin = 0.966, Tmax = 0.976	k = −9→9
4284 measured reflections	l = −11→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.0872P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.003
2864 reflections	Δρmax = 0.23 e Å^−3
205 parameters	Δρmin = −0.19 e Å^−3
19 restraints	Absolute structure: Flack (1983), 1288 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.93482 (9)	0.39396 (12)	0.89044 (9)	0.0501 (3)
O1	0.3637 (2)	0.3867 (4)	0.4751 (2)	0.0626 (7)
N1	0.7396 (3)	0.3105 (3)	0.6658 (3)	0.0377 (7)
N2	0.7006 (3)	0.5630 (4)	0.7268 (3)	0.0431 (8)
N3	0.7699 (3)	0.7903 (4)	0.8818 (3)	0.0588 (9)
C1	0.3495 (4)	0.3343 (5)	0.7246 (4)	0.0657 (12)
H1	0.2937	0.4191	0.6762	0.079*
C2	0.3285 (5)	0.2780 (7)	0.8354 (5)	0.0810 (15)
H2	0.2601	0.3266	0.8622	0.097*
C3	0.4074 (6)	0.1520 (7)	0.9055 (5)	0.0781 (14)
H3	0.3928	0.1151	0.9801	0.094*
C4	0.5074 (5)	0.0796 (6)	0.8668 (5)	0.0676 (12)
H4	0.5593	−0.0083	0.9134	0.081*
C5	0.5313 (4)	0.1379 (4)	0.7574 (4)	0.0507 (10)
H5	0.6016	0.0900	0.7326	0.061*
C6	0.4531 (4)	0.2649 (4)	0.6854 (4)	0.0428 (9)
C7	0.4669 (4)	0.3283 (4)	0.5640 (4)	0.0438 (9)
C8	0.6097 (3)	0.3175 (4)	0.5481 (3)	0.0374 (8)
C9	0.6117 (4)	0.3133 (5)	0.4264 (3)	0.0450 (9)
H9	0.5201	0.3063	0.3578	0.054*
C10	0.7333 (2)	0.3179 (3)	0.3828 (3)	0.0506 (9)
C11	0.7150 (3)	0.2416 (4)	0.2640 (3)	0.0704 (13)
H11	0.6264	0.1932	0.2141	0.085*
C12	0.8290 (4)	0.2376 (4)	0.2199 (3)	0.0958 (17)
H12	0.8167	0.1865	0.1404	0.115*
C13	0.9614 (3)	0.3099 (5)	0.2945 (4)	0.1010 (17)
H13	1.0377	0.3073	0.2649	0.121*
C14	0.9797 (2)	0.3863 (5)	0.4132 (3)	0.0951 (16)
H14	1.0683	0.4347	0.4631	0.114*
C15	0.8657 (3)	0.3903 (4)	0.4574 (2)	0.0708 (12)
H15	0.8780	0.4414	0.5368	0.085*
C16	0.8452 (4)	0.1804 (4)	0.6972 (4)	0.0471 (9)
H16A	0.9097	0.1940	0.6499	0.057*
H16B	0.7955	0.0788	0.6718	0.057*
C17	0.9300 (4)	0.1865 (5)	0.8442 (4)	0.0575 (11)
H17A	1.0281	0.1461	0.8664	0.069*
H17B	0.8826	0.1230	0.8905	0.069*
C18	0.7760 (4)	0.4323 (4)	0.7513 (3)	0.0372 (9)
C19	0.7429 (4)	0.6805 (4)	0.8146 (4)	0.0427 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0462 (5)	0.0512 (6)	0.0383 (5)	0.0047 (5)	0.0000 (4)	−0.0010 (5)
O1	0.0382 (13)	0.0832 (19)	0.0553 (15)	0.0111 (16)	0.0056 (12)	0.0101 (18)
N1	0.0321 (16)	0.0376 (16)	0.0376 (17)	0.0036 (14)	0.0070 (13)	−0.0046 (15)
N2	0.0376 (17)	0.0407 (19)	0.0430 (19)	0.0016 (15)	0.0067 (14)	−0.0083 (14)
N3	0.058 (2)	0.056 (2)	0.054 (2)	0.0010 (18)	0.0134 (16)	−0.0140 (19)
C1	0.058 (3)	0.075 (3)	0.064 (3)	0.012 (2)	0.023 (2)	−0.006 (2)
C2	0.075 (3)	0.110 (4)	0.071 (3)	0.004 (3)	0.044 (3)	−0.018 (3)
C3	0.092 (4)	0.096 (4)	0.057 (3)	−0.005 (3)	0.042 (3)	−0.004 (3)
C4	0.081 (3)	0.063 (3)	0.066 (3)	−0.002 (2)	0.036 (3)	0.004 (2)
C5	0.052 (2)	0.050 (2)	0.054 (3)	−0.0039 (19)	0.024 (2)	−0.004 (2)
C6	0.035 (2)	0.045 (2)	0.046 (2)	−0.0003 (16)	0.0124 (17)	−0.0078 (18)
C7	0.040 (2)	0.042 (2)	0.043 (2)	−0.0030 (17)	0.0091 (17)	−0.0049 (19)
C8	0.0347 (19)	0.0334 (19)	0.035 (2)	−0.0047 (16)	0.0037 (15)	−0.0018 (17)
C9	0.040 (2)	0.047 (2)	0.038 (2)	−0.0022 (17)	0.0038 (16)	0.0017 (18)
C10	0.047 (2)	0.053 (2)	0.047 (2)	0.002 (2)	0.0137 (18)	0.013 (2)
C11	0.076 (3)	0.073 (3)	0.072 (3)	−0.007 (2)	0.039 (3)	−0.011 (3)
C12	0.116 (4)	0.094 (3)	0.101 (3)	0.004 (3)	0.068 (3)	−0.011 (3)
C13	0.093 (3)	0.105 (3)	0.124 (4)	0.007 (3)	0.064 (3)	0.018 (3)
C14	0.070 (3)	0.113 (3)	0.100 (3)	−0.018 (3)	0.030 (2)	0.032 (3)
C15	0.057 (2)	0.097 (3)	0.056 (2)	−0.027 (3)	0.019 (2)	0.006 (3)
C16	0.043 (2)	0.040 (2)	0.051 (2)	0.0080 (17)	0.0091 (18)	−0.0014 (19)
C17	0.052 (3)	0.050 (2)	0.055 (2)	0.009 (2)	0.003 (2)	0.003 (2)
C18	0.0340 (19)	0.042 (2)	0.0357 (19)	0.0011 (15)	0.0129 (15)	0.0002 (16)
C19	0.037 (2)	0.043 (2)	0.043 (2)	0.0045 (17)	0.0097 (17)	0.003 (2)

Geometric parameters (Å, º)

S1—C18	1.744 (3)	C7—C8	1.495 (5)
S1—C17	1.807 (4)	C8—C9	1.333 (5)
O1—C7	1.209 (4)	C9—C10	1.458 (4)
N1—C18	1.335 (4)	C9—H9	0.9300
N1—C8	1.426 (4)	C10—C11	1.3900
N1—C16	1.460 (4)	C10—C15	1.3900
N2—C18	1.296 (4)	C11—C12	1.3900
N2—C19	1.323 (5)	C11—H11	0.9300
N3—C19	1.142 (4)	C12—C13	1.3900
C1—C2	1.384 (6)	C12—H12	0.9300
C1—C6	1.384 (5)	C13—C14	1.3900
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.361 (7)	C14—C15	1.3900
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.361 (6)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.495 (5)
C4—C5	1.390 (5)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C6	1.373 (5)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—C7	1.479 (5)
C18—S1—C17	91.03 (18)	C11—C10—C9	117.5 (2)
C18—N1—C8	120.2 (3)	C15—C10—C9	122.4 (2)
C18—N1—C16	115.6 (3)	C10—C11—C12	120.0
C8—N1—C16	124.1 (3)	C10—C11—H11	120.0
C18—N2—C19	118.9 (3)	C12—C11—H11	120.0
C2—C1—C6	120.3 (4)	C13—C12—C11	120.0
C2—C1—H1	119.9	C13—C12—H12	120.0
C6—C1—H1	119.9	C11—C12—H12	120.0
C3—C2—C1	120.4 (5)	C12—C13—C14	120.0
C3—C2—H2	119.8	C12—C13—H13	120.0
C1—C2—H2	119.8	C14—C13—H13	120.0
C2—C3—C4	120.3 (5)	C15—C14—C13	120.0
C2—C3—H3	119.9	C15—C14—H14	120.0
C4—C3—H3	119.9	C13—C14—H14	120.0
C3—C4—C5	119.6 (5)	C14—C15—C10	120.0
C3—C4—H4	120.2	C14—C15—H15	120.0
C5—C4—H4	120.2	C10—C15—H15	120.0
C6—C5—C4	121.1 (4)	N1—C16—C17	106.4 (3)
C6—C5—H5	119.5	N1—C16—H16A	110.4
C4—C5—H5	119.5	C17—C16—H16A	110.4
C5—C6—C1	118.3 (4)	N1—C16—H16B	110.4
C5—C6—C7	124.2 (3)	C17—C16—H16B	110.4
C1—C6—C7	117.4 (4)	H16A—C16—H16B	108.6
O1—C7—C6	121.3 (3)	C16—C17—S1	105.9 (3)
O1—C7—C8	118.7 (3)	C16—C17—H17A	110.6
C6—C7—C8	120.0 (3)	S1—C17—H17A	110.6
C9—C8—N1	122.5 (3)	C16—C17—H17B	110.6
C9—C8—C7	119.7 (3)	S1—C17—H17B	110.6
N1—C8—C7	117.9 (3)	H17A—C17—H17B	108.7
C8—C9—C10	130.9 (3)	N2—C18—N1	121.6 (3)
C8—C9—H9	114.6	N2—C18—S1	126.3 (3)
C10—C9—H9	114.6	N1—C18—S1	112.1 (2)
C11—C10—C15	120.0	N3—C19—N2	173.7 (4)
C6—C1—C2—C3	−1.3 (7)	C8—C9—C10—C11	151.0 (4)
C1—C2—C3—C4	−0.2 (8)	C8—C9—C10—C15	−26.8 (5)
C2—C3—C4—C5	1.7 (8)	C15—C10—C11—C12	0.0
C3—C4—C5—C6	−1.7 (7)	C9—C10—C11—C12	−177.8 (3)
C4—C5—C6—C1	0.2 (6)	C10—C11—C12—C13	0.0
C4—C5—C6—C7	−176.7 (4)	C11—C12—C13—C14	0.0
C2—C1—C6—C5	1.3 (6)	C12—C13—C14—C15	0.0
C2—C1—C6—C7	178.4 (4)	C13—C14—C15—C10	0.0
C5—C6—C7—O1	147.8 (4)	C11—C10—C15—C14	0.0
C1—C6—C7—O1	−29.1 (5)	C9—C10—C15—C14	177.7 (3)
C5—C6—C7—C8	−30.7 (5)	C18—N1—C16—C17	25.0 (4)
C1—C6—C7—C8	152.4 (3)	C8—N1—C16—C17	−159.2 (3)
C18—N1—C8—C9	117.7 (4)	N1—C16—C17—S1	−30.8 (4)
C16—N1—C8—C9	−57.9 (5)	C18—S1—C17—C16	24.4 (3)
C18—N1—C8—C7	−62.8 (4)	C19—N2—C18—N1	−179.2 (3)
C16—N1—C8—C7	121.6 (4)	C19—N2—C18—S1	−1.4 (5)
O1—C7—C8—C9	−25.1 (5)	C8—N1—C18—N2	−4.2 (5)
C6—C7—C8—C9	153.4 (3)	C16—N1—C18—N2	171.8 (3)
O1—C7—C8—N1	155.4 (4)	C8—N1—C18—S1	177.7 (2)
C6—C7—C8—N1	−26.0 (4)	C16—N1—C18—S1	−6.4 (4)
N1—C8—C9—C10	−7.0 (6)	C17—S1—C18—N2	170.8 (3)
C7—C8—C9—C10	173.5 (4)	C17—S1—C18—N1	−11.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1^i	0.97	2.39	3.300 (5)	156

Symmetry code: (i) −x+1, y−1/2, −z+1.