2-(4-Chloro­phen­yl)-3-[5-(4-methoxy­phen­yl)-1,3,4-thia­diazol-2-yl]thia­zolidin-4-one

In the title compound, C₁₈H₁₄ClN₃O₂S₂, the thia­zolidine ring adopts an envelope conformation. There are inter­molecular C—H...O inter­actions, forming centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.052
• wR factor = 0.137
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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
   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
   1 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

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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.

2-(4-Chlorophenyl)-3-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]thiazolidin- 4-one

Crystal data

C18H14ClN3O2S2	F(000) = 832
Mr = 403.89	Dx = 1.496 Mg m^−3
Monoclinic, P21/n	Melting point = 473–474 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.4380 (13) Å	Cell parameters from 25 reflections
b = 31.803 (6) Å	θ = 10–12°
c = 9.2650 (19) Å	µ = 0.46 mm^−1
β = 109.08 (3)°	T = 293 K
V = 1792.8 (6) Å^3	Block, yellow
Z = 4	0.40 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2453 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 26.0°, θmin = 1.3°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→39
Tmin = 0.836, Tmax = 0.873	l = −11→10
3816 measured reflections	3 standard reflections every 200 reflections
3505 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)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 2.3P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3505 reflections	Δρmax = 0.47 e Å^−3
235 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (4)

Special details

Experimental. Spectroscopic analysis, ¹H NMR (CDCl₃, δ, p.p.m.): 7.84–7.79(d, 2H),7.37–7.32(m, 2H), 7.03–7.00 (t, 2H), 6.95–6.93 (d, 2H), 6.96 (s,1H),4.11–4.06(d, 1H), 3.87 (s,1H),3.83 (s, 3H).

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
Cl	0.7348 (3)	0.24799 (4)	−0.00829 (14)	0.0753 (4)
S1	0.31512 (14)	0.05189 (3)	0.41703 (10)	0.0355 (2)
S2	0.91017 (18)	0.16660 (4)	0.70437 (12)	0.0515 (3)
O1	−0.1718 (4)	−0.10762 (8)	−0.0496 (3)	0.0438 (6)
O2	0.3529 (4)	0.11141 (9)	0.6334 (3)	0.0524 (7)
N1	0.5600 (5)	0.03143 (10)	0.2587 (4)	0.0417 (7)
N2	0.6628 (5)	0.06572 (10)	0.3465 (4)	0.0425 (8)
N3	0.6289 (4)	0.11312 (9)	0.5302 (3)	0.0331 (6)
C1	−0.3652 (6)	−0.11969 (13)	−0.0178 (5)	0.0500 (10)
H1B	−0.4397	−0.1414	−0.0875	0.075*
H1C	−0.4604	−0.0958	−0.0294	0.075*
H1D	−0.3259	−0.1300	0.0850	0.075*
C2	−0.0436 (5)	−0.07679 (11)	0.0396 (4)	0.0340 (8)
C3	0.1322 (6)	−0.06375 (11)	−0.0042 (4)	0.0376 (8)
H3A	0.1565	−0.0759	−0.0886	0.045*
C4	0.2714 (6)	−0.03271 (11)	0.0772 (4)	0.0388 (8)
H4A	0.3897	−0.0242	0.0477	0.047*
C5	0.2365 (5)	−0.01394 (10)	0.2036 (4)	0.0324 (7)
C6	0.0588 (6)	−0.02738 (11)	0.2445 (4)	0.0394 (8)
H6A	0.0324	−0.0149	0.3276	0.047*
C7	−0.0807 (6)	−0.05884 (11)	0.1648 (4)	0.0401 (9)
H7A	−0.1977	−0.0677	0.1951	0.048*
C8	0.3789 (5)	0.02072 (11)	0.2826 (4)	0.0332 (8)
C9	0.5540 (5)	0.07890 (11)	0.4323 (4)	0.0317 (7)
C10	0.5270 (6)	0.12574 (12)	0.6318 (4)	0.0398 (9)
C11	0.6550 (7)	0.15904 (14)	0.7385 (5)	0.0546 (11)
H11A	0.6820	0.1504	0.8435	0.065*
H11B	0.5724	0.1851	0.7213	0.065*
C12	0.8306 (6)	0.13461 (11)	0.5297 (4)	0.0364 (8)
H12A	0.9452	0.1137	0.5366	0.044*
C13	0.7991 (5)	0.16178 (11)	0.3899 (4)	0.0337 (8)
C14	0.9333 (6)	0.15665 (11)	0.3021 (4)	0.0404 (9)
H14A	1.0379	0.1353	0.3256	0.048*
C15	0.9140 (7)	0.18305 (13)	0.1786 (4)	0.0467 (10)
H15A	1.0054	0.1796	0.1197	0.056*
C16	0.7582 (7)	0.21416 (12)	0.1451 (4)	0.0460 (9)
C17	0.6198 (7)	0.21933 (13)	0.2277 (5)	0.0529 (11)
H17A	0.5127	0.2402	0.2019	0.063*
C18	0.6409 (7)	0.19318 (12)	0.3502 (5)	0.0484 (10)
H18A	0.5474	0.1966	0.4074	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1176 (11)	0.0552 (7)	0.0551 (7)	−0.0093 (7)	0.0309 (7)	0.0163 (6)
S1	0.0329 (5)	0.0361 (5)	0.0403 (5)	−0.0052 (4)	0.0159 (4)	−0.0029 (4)
S2	0.0544 (6)	0.0545 (7)	0.0407 (5)	−0.0209 (5)	0.0089 (5)	−0.0064 (5)
O1	0.0395 (14)	0.0487 (16)	0.0453 (15)	−0.0098 (12)	0.0170 (12)	−0.0110 (12)
O2	0.0450 (16)	0.067 (2)	0.0527 (17)	−0.0122 (14)	0.0260 (14)	−0.0126 (14)
N1	0.0423 (18)	0.0380 (17)	0.0512 (19)	−0.0078 (14)	0.0241 (15)	−0.0061 (14)
N2	0.0402 (18)	0.0404 (18)	0.0517 (19)	−0.0093 (14)	0.0215 (15)	−0.0086 (15)
N3	0.0319 (15)	0.0322 (16)	0.0347 (15)	−0.0053 (12)	0.0103 (12)	−0.0031 (12)
C1	0.039 (2)	0.055 (3)	0.054 (2)	−0.0145 (19)	0.0122 (19)	−0.008 (2)
C2	0.0331 (18)	0.0305 (19)	0.0370 (19)	0.0015 (14)	0.0094 (15)	0.0037 (15)
C3	0.038 (2)	0.038 (2)	0.041 (2)	0.0016 (16)	0.0188 (16)	−0.0061 (16)
C4	0.038 (2)	0.040 (2)	0.045 (2)	−0.0023 (16)	0.0224 (17)	−0.0001 (17)
C5	0.0334 (18)	0.0254 (17)	0.0390 (19)	0.0014 (14)	0.0127 (15)	0.0049 (14)
C6	0.046 (2)	0.039 (2)	0.0381 (19)	−0.0053 (17)	0.0202 (17)	−0.0035 (16)
C7	0.042 (2)	0.042 (2)	0.043 (2)	−0.0068 (17)	0.0224 (17)	0.0000 (17)
C8	0.0340 (18)	0.0321 (19)	0.0342 (18)	0.0009 (15)	0.0120 (15)	0.0018 (15)
C9	0.0286 (17)	0.0340 (19)	0.0331 (18)	−0.0016 (14)	0.0108 (14)	0.0012 (15)
C10	0.041 (2)	0.047 (2)	0.0324 (19)	0.0020 (17)	0.0128 (16)	0.0007 (16)
C11	0.059 (3)	0.057 (3)	0.049 (2)	−0.007 (2)	0.019 (2)	−0.014 (2)
C12	0.0330 (18)	0.0332 (19)	0.041 (2)	−0.0050 (15)	0.0100 (16)	0.0011 (16)
C13	0.0326 (18)	0.0312 (19)	0.0368 (18)	−0.0062 (14)	0.0108 (15)	−0.0015 (15)
C14	0.038 (2)	0.038 (2)	0.046 (2)	0.0024 (16)	0.0153 (17)	−0.0012 (17)
C15	0.050 (2)	0.055 (3)	0.041 (2)	−0.0059 (19)	0.0221 (19)	−0.0009 (18)
C16	0.065 (3)	0.032 (2)	0.040 (2)	−0.0082 (19)	0.0152 (19)	0.0016 (16)
C17	0.068 (3)	0.037 (2)	0.057 (3)	0.017 (2)	0.024 (2)	0.0108 (19)
C18	0.056 (2)	0.045 (2)	0.054 (2)	0.0145 (19)	0.031 (2)	0.0089 (19)

Geometric parameters (Å, º)

Cl—C16	1.749 (4)	C4—H4A	0.930
S1—C9	1.726 (3)	C5—C6	1.385 (5)
S1—C8	1.743 (3)	C5—C8	1.467 (5)
S2—C11	1.788 (4)	C6—C7	1.385 (5)
S2—C12	1.837 (4)	C6—H6A	0.930
O1—C2	1.371 (4)	C7—H7A	0.930
O1—C1	1.423 (4)	C10—C11	1.499 (5)
O2—C10	1.215 (4)	C11—H11A	0.970
N1—C8	1.301 (4)	C11—H11B	0.970
N1—N2	1.392 (4)	C12—C13	1.514 (5)
N2—C9	1.289 (4)	C12—H12A	0.980
N3—C10	1.371 (4)	C13—C14	1.376 (5)
N3—C9	1.398 (4)	C13—C18	1.387 (5)
N3—C12	1.469 (4)	C14—C15	1.392 (5)
C1—H1B	0.960	C14—H14A	0.930
C1—H1C	0.960	C15—C16	1.370 (6)
C1—H1D	0.960	C15—H15A	0.930
C2—C7	1.382 (5)	C16—C17	1.362 (6)
C2—C3	1.385 (5)	C17—C18	1.377 (5)
C3—C4	1.380 (5)	C17—H17A	0.930
C3—H3A	0.930	C18—H18A	0.930
C4—C5	1.396 (5)
C9—S1—C8	85.97 (16)	N2—C9—S1	115.9 (3)
C11—S2—C12	94.24 (17)	N3—C9—S1	123.3 (2)
C2—O1—C1	117.6 (3)	O2—C10—N3	123.3 (3)
C8—N1—N2	112.7 (3)	O2—C10—C11	124.6 (3)
C9—N2—N1	111.4 (3)	N3—C10—C11	112.1 (3)
C10—N3—C9	122.2 (3)	C10—C11—S2	108.5 (3)
C10—N3—C12	119.2 (3)	C10—C11—H11A	110.0
C9—N3—C12	118.5 (3)	S2—C11—H11A	110.0
O1—C1—H1B	109.5	C10—C11—H11B	110.0
O1—C1—H1C	109.5	S2—C11—H11B	110.0
H1B—C1—H1C	109.5	H11A—C11—H11B	108.4
O1—C1—H1D	109.5	N3—C12—C13	113.4 (3)
H1B—C1—H1D	109.5	N3—C12—S2	104.3 (2)
H1C—C1—H1D	109.5	C13—C12—S2	111.0 (2)
O1—C2—C7	124.5 (3)	N3—C12—H12A	109.3
O1—C2—C3	115.2 (3)	C13—C12—H12A	109.3
C7—C2—C3	120.3 (3)	S2—C12—H12A	109.3
C4—C3—C2	120.0 (3)	C14—C13—C18	118.5 (3)
C4—C3—H3A	120.0	C14—C13—C12	120.2 (3)
C2—C3—H3A	120.0	C18—C13—C12	121.3 (3)
C3—C4—C5	120.7 (3)	C13—C14—C15	120.7 (3)
C3—C4—H4A	119.6	C13—C14—H14A	119.7
C5—C4—H4A	119.6	C15—C14—H14A	119.7
C6—C5—C4	118.1 (3)	C16—C15—C14	118.9 (4)
C6—C5—C8	122.2 (3)	C16—C15—H15A	120.5
C4—C5—C8	119.6 (3)	C14—C15—H15A	120.5
C5—C6—C7	121.8 (3)	C17—C16—C15	121.6 (4)
C5—C6—H6A	119.1	C17—C16—Cl	119.0 (3)
C7—C6—H6A	119.1	C15—C16—Cl	119.4 (3)
C2—C7—C6	119.1 (3)	C16—C17—C18	118.9 (4)
C2—C7—H7A	120.5	C16—C17—H17A	120.5
C6—C7—H7A	120.5	C18—C17—H17A	120.5
N1—C8—C5	124.1 (3)	C17—C18—C13	121.3 (4)
N1—C8—S1	114.0 (3)	C17—C18—H18A	119.3
C5—C8—S1	121.9 (2)	C13—C18—H18A	119.3
N2—C9—N3	120.8 (3)
C8—N1—N2—C9	0.2 (4)	C8—S1—C9—N3	−179.9 (3)
C1—O1—C2—C7	4.9 (5)	C9—N3—C10—O2	−8.2 (6)
C1—O1—C2—C3	−174.8 (3)	C12—N3—C10—O2	175.3 (4)
O1—C2—C3—C4	179.7 (3)	C9—N3—C10—C11	172.0 (3)
C7—C2—C3—C4	0.0 (5)	C12—N3—C10—C11	−4.5 (5)
C2—C3—C4—C5	−0.4 (5)	O2—C10—C11—S2	174.9 (3)
C3—C4—C5—C6	0.0 (5)	N3—C10—C11—S2	−5.3 (4)
C3—C4—C5—C8	−176.3 (3)	C12—S2—C11—C10	10.2 (3)
C4—C5—C6—C7	0.7 (5)	C10—N3—C12—C13	−109.4 (3)
C8—C5—C6—C7	177.0 (3)	C9—N3—C12—C13	74.0 (4)
O1—C2—C7—C6	−178.9 (3)	C10—N3—C12—S2	11.5 (4)
C3—C2—C7—C6	0.7 (5)	C9—N3—C12—S2	−165.1 (2)
C5—C6—C7—C2	−1.1 (6)	C11—S2—C12—N3	−11.8 (3)
N2—N1—C8—C5	179.1 (3)	C11—S2—C12—C13	110.6 (3)
N2—N1—C8—S1	−0.1 (4)	N3—C12—C13—C14	−126.7 (3)
C6—C5—C8—N1	172.5 (3)	S2—C12—C13—C14	116.3 (3)
C4—C5—C8—N1	−11.3 (5)	N3—C12—C13—C18	55.6 (5)
C6—C5—C8—S1	−8.4 (5)	S2—C12—C13—C18	−61.4 (4)
C4—C5—C8—S1	167.8 (3)	C18—C13—C14—C15	1.5 (5)
C9—S1—C8—N1	−0.1 (3)	C12—C13—C14—C15	−176.3 (3)
C9—S1—C8—C5	−179.3 (3)	C13—C14—C15—C16	−0.4 (6)
N1—N2—C9—N3	179.8 (3)	C14—C15—C16—C17	−1.2 (6)
N1—N2—C9—S1	−0.3 (4)	C14—C15—C16—Cl	179.1 (3)
C10—N3—C9—N2	−174.6 (3)	C15—C16—C17—C18	1.5 (7)
C12—N3—C9—N2	1.9 (5)	Cl—C16—C17—C18	−178.8 (3)
C10—N3—C9—S1	5.6 (5)	C16—C17—C18—C13	−0.3 (7)
C12—N3—C9—S1	−177.9 (2)	C14—C13—C18—C17	−1.2 (6)
C8—S1—C9—N2	0.2 (3)	C12—C13—C18—C17	176.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O2^i	0.93	2.55	3.392 (8)	151

Symmetry code: (i) −x, −y, −z+1.