2-Phenyl-3-{5-[3-(trifluoro­meth­yl)phen­yl]-1,3,4-thia­diazol-2-yl}­thia­zolidin-4-one

The title compound, C₁₈H₁₂F₃N₃OS₂, was synthesized by the reaction of [(Z)-1-phenyl­methyl­idene]{5-[3-(trifluoro­meth­yl)phen­yl]-1,3,4-thia­diazol-2-­yl}amine and mercaptoacetic acid. In the structure there are intra­molecular C—H...S and C—H...N and inter­molecular C—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.131
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.20 Sigma
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      13.00 Deg.
              F3'  -C18  -F3      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      17.10 Deg.
              F2'  -C18  -F2      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.90 Deg.
              F1'  -C18  -F1      1.555   1.555   1.555

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
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius,1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

3-{5-[3-(Trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}- 2-phenylthiazolidin-4-one

Crystal data

C18H12F3N3OS2	Z = 2
Mr = 407.43	F(000) = 416
Triclinic, P1	Dx = 1.557 Mg m^−3
Hall symbol: -P 1	Melting point = 452–453 K
a = 7.5370 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.538 (2) Å	Cell parameters from 25 reflections
c = 11.380 (2) Å	θ = 10–12°
α = 79.86 (3)°	µ = 0.35 mm^−1
β = 78.03 (3)°	T = 293 K
γ = 84.70 (3)°	Block, colorless
V = 868.9 (3) Å^3	0.40 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2823 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.872, Tmax = 0.902	l = −13→14
3679 measured reflections	3 standard reflections every 200 reflections
3405 independent reflections	intensity decay: none

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3405 reflections	Δρmax = 0.33 e Å^−3
272 parameters	Δρmin = −0.32 e Å^−3
36 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0016 (5)

Special details

Experimental. Spectroscopic analysis, ¹H NMR (CDCl₃, δ, p.p.m.): 8.20–7.26(m, 9H), 6.76(s, 1H), 4.20–3.88(m, 2H).

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	Occ. (<1)
S1	0.42686 (8)	0.68681 (7)	0.48054 (6)	0.0549 (2)
S2	0.24768 (6)	0.46681 (5)	0.13863 (4)	0.03953 (17)
F1	−0.422 (2)	−0.0008 (12)	0.176 (2)	0.095 (4)	0.53 (6)
F2	−0.539 (3)	0.1814 (19)	0.2305 (18)	0.087 (4)	0.53 (6)
F3	−0.546 (3)	0.144 (3)	0.055 (2)	0.105 (5)	0.53 (6)
F2'	−0.517 (3)	0.150 (3)	0.2483 (17)	0.081 (4)	0.47 (6)
F1'	−0.420 (2)	0.0073 (13)	0.142 (2)	0.077 (3)	0.47 (6)
F3'	−0.564 (2)	0.1659 (19)	0.0680 (19)	0.079 (3)	0.47 (6)
O	0.5429 (2)	0.58159 (18)	0.16410 (15)	0.0591 (5)
N1	0.2961 (2)	0.60499 (16)	0.31335 (14)	0.0377 (4)
N2	0.0151 (2)	0.52331 (17)	0.32498 (15)	0.0417 (4)
N3	−0.0724 (2)	0.44841 (17)	0.26988 (15)	0.0419 (4)
C1	0.0389 (4)	0.9932 (2)	0.3088 (2)	0.0602 (6)
H1A	0.0779	1.0641	0.2510	0.072*
C2	−0.1331 (4)	0.9974 (2)	0.3783 (2)	0.0564 (6)
H2B	−0.2100	1.0712	0.3686	0.068*
C3	−0.1902 (3)	0.8919 (3)	0.4621 (2)	0.0587 (6)
H3B	−0.3064	0.8941	0.5097	0.070*
C4	−0.0760 (3)	0.7819 (2)	0.4764 (2)	0.0486 (5)
H4A	−0.1166	0.7104	0.5328	0.058*
C5	0.0983 (3)	0.77758 (18)	0.40725 (17)	0.0365 (4)
C6	0.1547 (3)	0.8848 (2)	0.3240 (2)	0.0497 (5)
H6A	0.2718	0.8841	0.2776	0.060*
C7	0.2238 (3)	0.65840 (19)	0.42685 (18)	0.0378 (4)
H7A	0.1563	0.5922	0.4864	0.045*
C8	0.5735 (3)	0.6818 (2)	0.3341 (2)	0.0530 (6)
H8A	0.6012	0.7687	0.2936	0.064*
H8B	0.6866	0.6333	0.3442	0.064*
C9	0.4763 (3)	0.6180 (2)	0.2594 (2)	0.0435 (5)
C10	0.1825 (3)	0.53877 (17)	0.26751 (17)	0.0342 (4)
C11	0.0295 (2)	0.41173 (18)	0.17300 (17)	0.0351 (4)
C12	−0.0348 (3)	0.32625 (18)	0.10279 (17)	0.0362 (4)
C13	−0.2046 (3)	0.27643 (19)	0.14750 (18)	0.0387 (4)
H13A	−0.2779	0.3009	0.2172	0.046*
C14	−0.2636 (3)	0.1900 (2)	0.08725 (19)	0.0416 (5)
C15	−0.1572 (3)	0.1552 (2)	−0.0186 (2)	0.0517 (6)
H15A	−0.1976	0.0965	−0.0580	0.062*
C16	0.0075 (3)	0.2076 (2)	−0.0648 (2)	0.0543 (6)
H16A	0.0774	0.1863	−0.1369	0.065*
C17	0.0707 (3)	0.2927 (2)	−0.00421 (19)	0.0443 (5)
H17A	0.1834	0.3271	−0.0352	0.053*
C18	−0.4411 (3)	0.1295 (2)	0.1371 (2)	0.0547 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0428 (3)	0.0746 (4)	0.0542 (4)	0.0023 (3)	−0.0150 (3)	−0.0251 (3)
S2	0.0317 (3)	0.0458 (3)	0.0405 (3)	−0.0058 (2)	0.0027 (2)	−0.0152 (2)
F1	0.070 (4)	0.068 (4)	0.131 (9)	−0.029 (3)	−0.014 (4)	0.035 (5)
F2	0.060 (4)	0.083 (5)	0.110 (8)	−0.027 (3)	0.021 (4)	−0.028 (4)
F3	0.064 (7)	0.156 (10)	0.112 (6)	−0.034 (6)	−0.042 (5)	−0.021 (6)
F2'	0.066 (6)	0.119 (10)	0.059 (4)	−0.049 (6)	0.016 (3)	−0.031 (5)
F1'	0.076 (4)	0.037 (4)	0.109 (8)	−0.019 (3)	0.001 (4)	−0.005 (4)
F3'	0.044 (3)	0.098 (5)	0.093 (6)	−0.006 (3)	−0.025 (4)	0.002 (5)
O	0.0365 (8)	0.0846 (12)	0.0563 (10)	−0.0123 (8)	0.0086 (7)	−0.0285 (9)
N1	0.0317 (8)	0.0413 (9)	0.0392 (9)	−0.0064 (7)	0.0013 (7)	−0.0119 (7)
N2	0.0369 (9)	0.0474 (10)	0.0396 (9)	−0.0117 (7)	0.0035 (7)	−0.0120 (7)
N3	0.0357 (9)	0.0484 (10)	0.0415 (9)	−0.0112 (7)	0.0009 (7)	−0.0126 (7)
C1	0.0736 (17)	0.0476 (13)	0.0578 (14)	0.0009 (12)	−0.0134 (13)	−0.0054 (11)
C2	0.0632 (15)	0.0514 (13)	0.0613 (14)	0.0133 (11)	−0.0249 (12)	−0.0207 (11)
C3	0.0386 (12)	0.0733 (16)	0.0676 (15)	0.0061 (11)	−0.0080 (11)	−0.0280 (13)
C4	0.0392 (11)	0.0516 (13)	0.0531 (13)	−0.0068 (9)	−0.0006 (9)	−0.0112 (10)
C5	0.0360 (10)	0.0404 (10)	0.0355 (10)	−0.0053 (8)	−0.0038 (8)	−0.0143 (8)
C6	0.0495 (12)	0.0470 (12)	0.0492 (12)	−0.0044 (10)	−0.0009 (10)	−0.0080 (10)
C7	0.0370 (10)	0.0402 (10)	0.0365 (10)	−0.0058 (8)	−0.0026 (8)	−0.0110 (8)
C8	0.0337 (11)	0.0645 (14)	0.0633 (14)	−0.0070 (10)	−0.0053 (10)	−0.0200 (12)
C9	0.0321 (10)	0.0479 (12)	0.0489 (12)	−0.0053 (9)	0.0001 (9)	−0.0113 (9)
C10	0.0323 (9)	0.0331 (9)	0.0352 (10)	−0.0030 (7)	−0.0008 (7)	−0.0063 (8)
C11	0.0326 (9)	0.0344 (9)	0.0365 (10)	−0.0052 (7)	−0.0020 (8)	−0.0046 (8)
C12	0.0371 (10)	0.0347 (10)	0.0357 (10)	−0.0028 (8)	−0.0065 (8)	−0.0031 (8)
C13	0.0382 (10)	0.0396 (10)	0.0378 (10)	−0.0045 (8)	−0.0044 (8)	−0.0071 (8)
C14	0.0390 (11)	0.0405 (11)	0.0457 (11)	−0.0056 (8)	−0.0095 (9)	−0.0051 (9)
C15	0.0557 (14)	0.0521 (13)	0.0531 (13)	−0.0086 (10)	−0.0119 (11)	−0.0202 (10)
C16	0.0547 (14)	0.0634 (15)	0.0465 (12)	−0.0063 (11)	−0.0006 (10)	−0.0233 (11)
C17	0.0381 (11)	0.0502 (12)	0.0431 (11)	−0.0056 (9)	−0.0015 (9)	−0.0096 (9)
C18	0.0473 (13)	0.0567 (15)	0.0624 (15)	−0.0141 (11)	−0.0112 (11)	−0.0096 (12)

Geometric parameters (Å, º)

S1—C8	1.805 (2)	C3—H3B	0.9300
S1—C7	1.828 (2)	C4—C5	1.385 (3)
S2—C10	1.7295 (19)	C4—H4A	0.9300
S2—C11	1.7385 (19)	C5—C6	1.378 (3)
F1—C18	1.371 (14)	C5—C7	1.514 (3)
F2—C18	1.334 (16)	C6—H6A	0.9300
F3—C18	1.327 (18)	C7—H7A	0.9800
F2'—C18	1.323 (15)	C8—C9	1.504 (3)
F1'—C18	1.275 (12)	C8—H8A	0.9700
F3'—C18	1.326 (17)	C8—H8B	0.9700
O—C9	1.208 (3)	C11—C12	1.476 (3)
N1—C9	1.378 (2)	C12—C13	1.390 (3)
N1—C10	1.385 (3)	C12—C17	1.392 (3)
N1—C7	1.480 (2)	C13—C14	1.385 (3)
N2—C10	1.305 (2)	C13—H13A	0.9300
N2—N3	1.376 (2)	C14—C15	1.389 (3)
N3—C11	1.303 (2)	C14—C18	1.494 (3)
C1—C2	1.373 (4)	C15—C16	1.370 (3)
C1—C6	1.380 (3)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.392 (3)
C2—C3	1.370 (4)	C16—H16A	0.9300
C2—H2B	0.9300	C17—H17A	0.9300
C3—C4	1.385 (3)
C8—S1—C7	93.43 (10)	N3—C11—C12	122.10 (17)
C10—S2—C11	85.90 (9)	N3—C11—S2	114.17 (15)
C9—N1—C10	122.03 (17)	C12—C11—S2	123.67 (14)
C9—N1—C7	119.02 (17)	C13—C12—C17	119.75 (19)
C10—N1—C7	118.90 (15)	C13—C12—C11	118.24 (18)
C10—N2—N3	111.35 (16)	C17—C12—C11	122.00 (18)
C11—N3—N2	113.12 (16)	C14—C13—C12	119.37 (19)
C2—C1—C6	120.7 (2)	C14—C13—H13A	120.3
C2—C1—H1A	119.7	C12—C13—H13A	120.3
C6—C1—H1A	119.7	C13—C14—C15	120.8 (2)
C3—C2—C1	119.3 (2)	C13—C14—C18	120.4 (2)
C3—C2—H2B	120.4	C15—C14—C18	118.8 (2)
C1—C2—H2B	120.4	C16—C15—C14	119.8 (2)
C2—C3—C4	120.4 (2)	C16—C15—H15A	120.1
C2—C3—H3B	119.8	C14—C15—H15A	120.1
C4—C3—H3B	119.8	C15—C16—C17	120.3 (2)
C3—C4—C5	120.5 (2)	C15—C16—H16A	119.9
C3—C4—H4A	119.7	C17—C16—H16A	119.9
C5—C4—H4A	119.7	C16—C17—C12	120.0 (2)
C6—C5—C4	118.5 (2)	C16—C17—H17A	120.0
C6—C5—C7	121.53 (18)	C12—C17—H17A	120.0
C4—C5—C7	119.95 (18)	F1'—C18—F2'	106.4 (11)
C5—C6—C1	120.6 (2)	F1'—C18—F3'	104.5 (13)
C5—C6—H6A	119.7	F2'—C18—F3'	107.1 (14)
C1—C6—H6A	119.7	F1'—C18—F3	93.5 (12)
N1—C7—C5	112.51 (16)	F2'—C18—F3	118.0 (12)
N1—C7—S1	104.07 (13)	F3'—C18—F3	13 (2)
C5—C7—S1	113.96 (13)	F1'—C18—F2	120.7 (10)
N1—C7—H7A	108.7	F2'—C18—F2	17.1 (16)
C5—C7—H7A	108.7	F3'—C18—F2	93.3 (13)
S1—C7—H7A	108.7	F3—C18—F2	105.5 (13)
C9—C8—S1	108.04 (15)	F1'—C18—F1	15.9 (13)
C9—C8—H8A	110.1	F2'—C18—F1	91.6 (10)
S1—C8—H8A	110.1	F3'—C18—F1	115.4 (11)
C9—C8—H8B	110.1	F3—C18—F1	106.0 (11)
S1—C8—H8B	110.1	F2—C18—F1	106.9 (10)
H8A—C8—H8B	108.4	F1'—C18—C14	110.4 (8)
O—C9—N1	122.7 (2)	F2'—C18—C14	114.2 (8)
O—C9—C8	126.02 (19)	F3'—C18—C14	113.6 (8)
N1—C9—C8	111.29 (18)	F3—C18—C14	112.0 (8)
N2—C10—N1	119.94 (17)	F2—C18—C14	112.9 (8)
N2—C10—S2	115.44 (15)	F1—C18—C14	113.0 (7)
N1—C10—S2	124.57 (14)
C10—N2—N3—C11	−0.9 (2)	C11—S2—C10—N2	−1.31 (16)
C6—C1—C2—C3	−0.9 (4)	C11—S2—C10—N1	176.22 (18)
C1—C2—C3—C4	−0.2 (4)	N2—N3—C11—C12	177.43 (17)
C2—C3—C4—C5	0.8 (4)	N2—N3—C11—S2	−0.1 (2)
C3—C4—C5—C6	−0.2 (3)	C10—S2—C11—N3	0.78 (15)
C3—C4—C5—C7	177.9 (2)	C10—S2—C11—C12	−176.74 (17)
C4—C5—C6—C1	−0.9 (3)	N3—C11—C12—C13	−4.8 (3)
C7—C5—C6—C1	−179.0 (2)	S2—C11—C12—C13	172.50 (14)
C2—C1—C6—C5	1.5 (4)	N3—C11—C12—C17	176.54 (19)
C9—N1—C7—C5	108.2 (2)	S2—C11—C12—C17	−6.1 (3)
C10—N1—C7—C5	−74.5 (2)	C17—C12—C13—C14	2.5 (3)
C9—N1—C7—S1	−15.7 (2)	C11—C12—C13—C14	−176.20 (18)
C10—N1—C7—S1	161.67 (14)	C12—C13—C14—C15	−1.6 (3)
C6—C5—C7—N1	−56.8 (2)	C12—C13—C14—C18	176.66 (19)
C4—C5—C7—N1	125.1 (2)	C13—C14—C15—C16	−0.5 (3)
C6—C5—C7—S1	61.3 (2)	C18—C14—C15—C16	−178.8 (2)
C4—C5—C7—S1	−116.75 (19)	C14—C15—C16—C17	1.8 (4)
C8—S1—C7—N1	18.23 (14)	C15—C16—C17—C12	−1.0 (4)
C8—S1—C7—C5	−104.67 (16)	C13—C12—C17—C16	−1.2 (3)
C7—S1—C8—C9	−17.55 (17)	C11—C12—C17—C16	177.4 (2)
C10—N1—C9—O	5.9 (3)	C13—C14—C18—F1'	−129.6 (13)
C7—N1—C9—O	−176.9 (2)	C15—C14—C18—F1'	48.7 (13)
C10—N1—C9—C8	−174.12 (18)	C13—C14—C18—F2'	−9.7 (17)
C7—N1—C9—C8	3.1 (3)	C15—C14—C18—F2'	168.6 (16)
S1—C8—C9—O	−168.5 (2)	C13—C14—C18—F3'	113.5 (12)
S1—C8—C9—N1	11.5 (2)	C15—C14—C18—F3'	−68.2 (12)
N3—N2—C10—N1	−176.15 (16)	C13—C14—C18—F3	127.7 (15)
N3—N2—C10—S2	1.5 (2)	C15—C14—C18—F3	−54.0 (15)
C9—N1—C10—N2	176.58 (18)	C13—C14—C18—F2	8.9 (12)
C7—N1—C10—N2	−0.7 (3)	C15—C14—C18—F2	−172.8 (12)
C9—N1—C10—S2	−0.9 (3)	C13—C14—C18—F1	−112.6 (12)
C7—N1—C10—S2	−178.09 (14)	C15—C14—C18—F1	65.7 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···N2^i	0.97	2.62	3.573 (3)	168
C13—H13A···N3	0.93	2.52	2.831 (3)	100
C17—H17A···S2	0.93	2.81	3.192 (2)	106

Symmetry code: (i) x+1, y, z.