5-(4-Chloro­phen­oxy)-3,6-diphenyl-2-thioxo-2,3-dihydro­thia­zolo[4,5-d]pyrimidin-7(6H)-one dichloro­methane hemisolvate

In the title compound, C₂₃H₁₄ClN₃O₂S₂·0.5CH₂Cl₂, the mean plane of thiazolopyrimidine fragment makes dihedral angles of 65.8 (1)°, 80.1 (1)° and 55.5 (1)° with the two attached phenyl rings and the 4-chloro­phen­yloxy fragment. The crystal packing is stabilized by weak π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.058
• wR factor = 0.170
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  C15    ..  C24     ..       3.09 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  S2      ..       3.49 Ang.

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

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

5-(4-Chlorophenoxy)-3,6-diphenyl-2-thioxo-2,3-dihydrothiazolo [4,5-d]pyrimidin-7(6H)-one dichloromethane solvate

Crystal data

C23H14ClN3O2S2·0.5(CH2Cl2)	Z = 2
Mr = 506.42	F(000) = 518
Triclinic, P1	Dx = 1.484 Mg m^−3
a = 9.5480 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1732 (9) Å	Cell parameters from 5716 reflections
c = 11.9096 (9) Å	θ = 2.3–27.8°
α = 75.307 (1)°	µ = 0.50 mm^−1
β = 77.922 (1)°	T = 292 K
γ = 68.403 (1)°	Block, colourless
V = 1133.18 (15) Å^3	0.30 × 0.20 × 0.20 mm

Data collection

Bruker Smart Apex CCD area detector diffractometer	4051 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 27.0°, θmin = 1.8°
φ and ω scans	h = −12→12
12823 measured reflections	k = −14→14
4913 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0916P)^2 + 0.4546P] where P = (Fo^2 + 2Fc^2)/3
4913 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.84 e Å^−3
12 restraints	Δρmin = −0.69 e Å^−3

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	Occ. (<1)
S1	0.72032 (10)	−0.22941 (8)	1.18805 (6)	0.0620 (2)
Cl1	1.37604 (8)	−0.03181 (9)	0.38747 (7)	0.0655 (2)
N1	0.7867 (2)	−0.0766 (2)	0.98140 (17)	0.0406 (4)
N2	0.8158 (2)	0.0842 (2)	0.81072 (18)	0.0424 (5)
N3	0.6485 (2)	0.3019 (2)	0.81424 (18)	0.0416 (5)
O1	0.4638 (2)	0.35546 (19)	0.96901 (17)	0.0546 (5)
O2	0.8200 (2)	0.25690 (18)	0.65786 (16)	0.0532 (5)
S2	0.56530 (8)	0.05687 (7)	1.11221 (6)	0.0489 (2)
C6	0.9096 (3)	−0.1825 (2)	0.9389 (2)	0.0415 (5)
C5	0.8791 (3)	−0.2847 (3)	0.9153 (3)	0.0519 (6)
H5	0.7798	−0.2850	0.9263	0.062*
C4	0.9975 (4)	−0.3860 (3)	0.8753 (3)	0.0648 (8)
H4	0.9782	−0.4548	0.8583	0.078*
C3	1.1443 (4)	−0.3861 (3)	0.8603 (3)	0.0730 (9)
H3	1.2242	−0.4553	0.8342	0.088*
C2	1.1725 (4)	−0.2837 (4)	0.8839 (4)	0.0808 (11)
H2	1.2718	−0.2839	0.8734	0.097*
C1	1.0561 (3)	−0.1810 (3)	0.9226 (3)	0.0642 (8)
H1	1.0757	−0.1114	0.9378	0.077*
C7	0.7019 (3)	−0.0940 (3)	1.0900 (2)	0.0436 (5)
C8	0.7440 (3)	0.0517 (2)	0.9183 (2)	0.0382 (5)
C9	0.6265 (3)	0.1357 (2)	0.9767 (2)	0.0413 (5)
C10	0.5674 (3)	0.2718 (2)	0.9265 (2)	0.0420 (5)
C17	0.7643 (3)	0.2072 (2)	0.7643 (2)	0.0412 (5)
C11	0.6059 (3)	0.4382 (2)	0.7550 (2)	0.0458 (6)
C12	0.5130 (4)	0.4824 (4)	0.6695 (3)	0.0668 (8)
H12	0.4738	0.4267	0.6498	0.080*
C13	0.4786 (4)	0.6132 (4)	0.6126 (3)	0.0878 (13)
H13	0.4156	0.6455	0.5541	0.105*
C14	0.5375 (5)	0.6954 (4)	0.6425 (4)	0.0885 (13)
H14	0.5184	0.7815	0.6016	0.106*
C15	0.6223 (6)	0.6503 (3)	0.7307 (4)	0.0869 (12)
H15	0.6576	0.7069	0.7531	0.104*
C16	0.6576 (4)	0.5223 (3)	0.7883 (3)	0.0660 (8)
H16	0.7161	0.4924	0.8495	0.079*
C18	0.9540 (3)	0.1804 (2)	0.5982 (2)	0.0433 (5)
C19	0.9502 (3)	0.1826 (3)	0.4830 (2)	0.0493 (6)
H19	0.8604	0.2267	0.4499	0.059*
C20	1.0807 (3)	0.1189 (3)	0.4169 (2)	0.0483 (6)
H20	1.0803	0.1198	0.3386	0.058*
C21	1.2109 (3)	0.0541 (3)	0.4683 (2)	0.0464 (6)
C22	1.2154 (3)	0.0534 (3)	0.5837 (2)	0.0557 (7)
H22	1.3053	0.0104	0.6168	0.067*
C23	1.0839 (3)	0.1180 (3)	0.6492 (2)	0.0540 (7)
H23	1.0841	0.1187	0.7270	0.065*
C24	0.9100 (6)	0.5501 (8)	0.5591 (5)	0.209 (9)	0.50
H24A	0.8445	0.5110	0.6184	0.251*	0.50
H24B	0.8806	0.6421	0.5624	0.251*	0.50
Cl2	0.8995 (4)	0.5317 (2)	0.4202 (3)	0.2277 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0785 (5)	0.0604 (5)	0.0451 (4)	−0.0289 (4)	−0.0062 (3)	0.0006 (3)
Cl1	0.0466 (4)	0.0845 (6)	0.0531 (4)	−0.0150 (4)	0.0141 (3)	−0.0192 (4)
N1	0.0387 (10)	0.0422 (11)	0.0392 (10)	−0.0131 (8)	−0.0021 (8)	−0.0080 (8)
N2	0.0389 (10)	0.0426 (11)	0.0406 (11)	−0.0117 (9)	0.0055 (8)	−0.0108 (8)
N3	0.0399 (10)	0.0404 (11)	0.0409 (11)	−0.0114 (9)	0.0031 (8)	−0.0115 (8)
O1	0.0480 (10)	0.0505 (11)	0.0566 (11)	−0.0085 (9)	0.0103 (8)	−0.0213 (9)
O2	0.0549 (11)	0.0417 (9)	0.0455 (10)	−0.0088 (8)	0.0143 (8)	−0.0063 (8)
S2	0.0509 (4)	0.0545 (4)	0.0383 (3)	−0.0200 (3)	0.0089 (3)	−0.0120 (3)
C6	0.0381 (12)	0.0420 (12)	0.0399 (12)	−0.0106 (10)	−0.0032 (9)	−0.0056 (10)
C5	0.0471 (14)	0.0489 (14)	0.0587 (16)	−0.0179 (12)	−0.0004 (12)	−0.0109 (12)
C4	0.0675 (19)	0.0472 (15)	0.073 (2)	−0.0146 (14)	0.0045 (15)	−0.0188 (14)
C3	0.0582 (19)	0.0613 (19)	0.080 (2)	0.0002 (15)	0.0022 (16)	−0.0204 (17)
C2	0.0388 (15)	0.091 (3)	0.109 (3)	−0.0108 (16)	−0.0054 (17)	−0.033 (2)
C1	0.0431 (15)	0.073 (2)	0.084 (2)	−0.0216 (14)	−0.0044 (14)	−0.0291 (17)
C7	0.0451 (13)	0.0520 (14)	0.0381 (12)	−0.0220 (11)	−0.0037 (10)	−0.0089 (10)
C8	0.0362 (11)	0.0412 (12)	0.0385 (12)	−0.0152 (10)	−0.0013 (9)	−0.0093 (9)
C9	0.0404 (12)	0.0464 (13)	0.0371 (12)	−0.0173 (10)	0.0037 (9)	−0.0108 (10)
C10	0.0368 (12)	0.0474 (13)	0.0428 (13)	−0.0151 (10)	0.0026 (10)	−0.0149 (10)
C17	0.0395 (12)	0.0426 (13)	0.0401 (12)	−0.0149 (10)	0.0043 (9)	−0.0116 (10)
C11	0.0435 (13)	0.0410 (13)	0.0419 (13)	−0.0050 (10)	0.0030 (10)	−0.0095 (10)
C12	0.0533 (17)	0.074 (2)	0.0635 (19)	−0.0105 (15)	−0.0119 (14)	−0.0102 (16)
C13	0.070 (2)	0.090 (3)	0.064 (2)	0.012 (2)	−0.0166 (17)	0.003 (2)
C14	0.108 (3)	0.0461 (18)	0.073 (2)	0.0071 (19)	0.002 (2)	−0.0073 (17)
C15	0.131 (4)	0.0464 (17)	0.077 (2)	−0.026 (2)	−0.005 (2)	−0.0123 (17)
C16	0.090 (2)	0.0502 (16)	0.0585 (18)	−0.0218 (16)	−0.0135 (16)	−0.0103 (13)
C18	0.0449 (13)	0.0394 (12)	0.0401 (12)	−0.0160 (10)	0.0102 (10)	−0.0081 (10)
C19	0.0475 (14)	0.0481 (14)	0.0414 (13)	−0.0109 (11)	−0.0028 (11)	0.0001 (11)
C20	0.0518 (14)	0.0528 (15)	0.0338 (12)	−0.0157 (12)	0.0019 (10)	−0.0060 (10)
C21	0.0429 (13)	0.0533 (14)	0.0411 (13)	−0.0203 (11)	0.0104 (10)	−0.0123 (11)
C22	0.0397 (13)	0.082 (2)	0.0443 (14)	−0.0217 (13)	−0.0004 (11)	−0.0125 (13)
C23	0.0507 (15)	0.0769 (19)	0.0398 (13)	−0.0274 (14)	0.0027 (11)	−0.0180 (13)
C24	0.212 (18)	0.173 (15)	0.251 (19)	−0.146 (15)	−0.049 (14)	0.081 (13)
Cl2	0.291 (3)	0.1237 (15)	0.260 (3)	−0.0497 (18)	−0.153 (3)	0.0429 (17)

Geometric parameters (Å, º)

S1—C7	1.637 (3)	C9—C10	1.427 (4)
Cl1—C21	1.747 (3)	C11—C12	1.367 (4)
N1—C7	1.384 (3)	C11—C16	1.377 (4)
N1—C8	1.393 (3)	C12—C13	1.392 (5)
N1—C6	1.437 (3)	C12—H12	0.9300
N2—C17	1.291 (3)	C13—C14	1.385 (6)
N2—C8	1.350 (3)	C13—H13	0.9300
N3—C17	1.371 (3)	C14—C15	1.342 (6)
N3—C10	1.425 (3)	C14—H14	0.9300
N3—C11	1.449 (3)	C15—C16	1.369 (5)
O1—C10	1.208 (3)	C15—H15	0.9300
O2—C17	1.333 (3)	C16—H16	0.9300
O2—C18	1.412 (3)	C18—C23	1.363 (4)
S2—C9	1.727 (2)	C18—C19	1.374 (4)
S2—C7	1.754 (3)	C19—C20	1.378 (4)
C6—C1	1.377 (4)	C19—H19	0.9300
C6—C5	1.382 (4)	C20—C21	1.370 (4)
C5—C4	1.375 (4)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.383 (4)
C4—C3	1.375 (5)	C22—C23	1.383 (4)
C4—H4	0.9300	C22—H22	0.9300
C3—C2	1.372 (5)	C23—H23	0.9300
C3—H3	0.9300	C24—Cl2	1.746 (4)
C2—C1	1.371 (5)	C24—Cl2^i	1.748 (5)
C2—H2	0.9300	C24—H24A	0.9700
C1—H1	0.9300	C24—H24B	0.9700
C8—C9	1.361 (3)	Cl2—C24^i	1.748 (5)
C7—N1—C8	114.3 (2)	C12—C11—N3	120.2 (3)
C7—N1—C6	122.4 (2)	C16—C11—N3	118.9 (2)
C8—N1—C6	123.28 (19)	C11—C12—C13	118.2 (4)
C17—N2—C8	113.9 (2)	C11—C12—H12	120.9
C17—N3—C10	121.9 (2)	C13—C12—H12	120.9
C17—N3—C11	120.8 (2)	C14—C13—C12	120.5 (4)
C10—N3—C11	117.35 (19)	C14—C13—H13	119.8
C17—O2—C18	120.58 (19)	C12—C13—H13	119.8
C9—S2—C7	91.45 (12)	C15—C14—C13	119.7 (3)
C1—C6—C5	120.9 (3)	C15—C14—H14	120.2
C1—C6—N1	119.6 (2)	C13—C14—H14	120.2
C5—C6—N1	119.5 (2)	C14—C15—C16	121.0 (4)
C4—C5—C6	119.1 (3)	C14—C15—H15	119.5
C4—C5—H5	120.5	C16—C15—H15	119.5
C6—C5—H5	120.5	C15—C16—C11	119.6 (3)
C3—C4—C5	120.4 (3)	C15—C16—H16	120.2
C3—C4—H4	119.8	C11—C16—H16	120.2
C5—C4—H4	119.8	C23—C18—C19	121.9 (2)
C2—C3—C4	119.7 (3)	C23—C18—O2	121.5 (2)
C2—C3—H3	120.1	C19—C18—O2	116.4 (2)
C4—C3—H3	120.1	C18—C19—C20	119.4 (2)
C1—C2—C3	120.9 (3)	C18—C19—H19	120.3
C1—C2—H2	119.5	C20—C19—H19	120.3
C3—C2—H2	119.5	C21—C20—C19	118.9 (2)
C2—C1—C6	119.0 (3)	C21—C20—H20	120.5
C2—C1—H1	120.5	C19—C20—H20	120.5
C6—C1—H1	120.5	C20—C21—C22	121.7 (2)
N1—C7—S1	128.0 (2)	C20—C21—Cl1	119.7 (2)
N1—C7—S2	109.37 (18)	C22—C21—Cl1	118.6 (2)
S1—C7—S2	122.60 (15)	C23—C22—C21	118.9 (3)
N2—C8—C9	125.8 (2)	C23—C22—H22	120.6
N2—C8—N1	121.3 (2)	C21—C22—H22	120.6
C9—C8—N1	112.9 (2)	C18—C23—C22	119.2 (2)
C8—C9—C10	121.1 (2)	C18—C23—H23	120.4
C8—C9—S2	111.95 (19)	C22—C23—H23	120.4
C10—C9—S2	126.91 (18)	Cl2—C24—Cl2^i	104.7 (2)
O1—C10—N3	121.5 (2)	Cl2—C24—H24A	110.8
O1—C10—C9	127.4 (2)	Cl2^i—C24—H24A	110.8
N3—C10—C9	111.1 (2)	Cl2—C24—H24B	110.8
N2—C17—O2	122.3 (2)	Cl2^i—C24—H24B	110.8
N2—C17—N3	126.2 (2)	H24A—C24—H24B	108.9
O2—C17—N3	111.5 (2)	C24—Cl2—C24^i	75.3 (2)
C12—C11—C16	120.9 (3)
C7—N1—C6—C1	−113.6 (3)	C8—C9—C10—N3	−0.9 (3)
C8—N1—C6—C1	65.5 (3)	S2—C9—C10—N3	178.71 (18)
C7—N1—C6—C5	66.2 (3)	C8—N2—C17—O2	−179.2 (2)
C8—N1—C6—C5	−114.7 (3)	C8—N2—C17—N3	0.2 (4)
C1—C6—C5—C4	0.2 (4)	C18—O2—C17—N2	−9.8 (4)
N1—C6—C5—C4	−179.6 (3)	C18—O2—C17—N3	170.7 (2)
C6—C5—C4—C3	0.7 (5)	C10—N3—C17—N2	−1.6 (4)
C5—C4—C3—C2	−0.9 (6)	C11—N3—C17—N2	177.1 (2)
C4—C3—C2—C1	0.2 (6)	C10—N3—C17—O2	177.8 (2)
C3—C2—C1—C6	0.6 (6)	C11—N3—C17—O2	−3.4 (3)
C5—C6—C1—C2	−0.8 (5)	C17—N3—C11—C12	81.6 (3)
N1—C6—C1—C2	179.0 (3)	C10—N3—C11—C12	−99.6 (3)
C8—N1—C7—S1	−179.34 (18)	C17—N3—C11—C16	−100.0 (3)
C6—N1—C7—S1	−0.2 (3)	C10—N3—C11—C16	78.8 (3)
C8—N1—C7—S2	−0.2 (2)	C16—C11—C12—C13	3.4 (5)
C6—N1—C7—S2	178.97 (17)	N3—C11—C12—C13	−178.2 (3)
C9—S2—C7—N1	0.11 (18)	C11—C12—C13—C14	0.0 (5)
C9—S2—C7—S1	179.31 (17)	C12—C13—C14—C15	−3.2 (6)
C17—N2—C8—C9	0.8 (4)	C13—C14—C15—C16	3.1 (7)
C17—N2—C8—N1	−179.2 (2)	C14—C15—C16—C11	0.3 (6)
C7—N1—C8—N2	−179.9 (2)	C12—C11—C16—C15	−3.6 (5)
C6—N1—C8—N2	1.0 (3)	N3—C11—C16—C15	178.0 (3)
C7—N1—C8—C9	0.2 (3)	C17—O2—C18—C23	−52.4 (4)
C6—N1—C8—C9	−179.0 (2)	C17—O2—C18—C19	133.5 (3)
N2—C8—C9—C10	−0.4 (4)	C23—C18—C19—C20	0.7 (4)
N1—C8—C9—C10	179.6 (2)	O2—C18—C19—C20	174.8 (2)
N2—C8—C9—S2	179.96 (19)	C18—C19—C20—C21	0.4 (4)
N1—C8—C9—S2	−0.1 (3)	C19—C20—C21—C22	−1.4 (4)
C7—S2—C9—C8	0.0 (2)	C19—C20—C21—Cl1	177.9 (2)
C7—S2—C9—C10	−179.7 (2)	C20—C21—C22—C23	1.3 (4)
C17—N3—C10—O1	−178.7 (2)	Cl1—C21—C22—C23	−178.1 (2)
C11—N3—C10—O1	2.5 (4)	C19—C18—C23—C22	−0.8 (4)
C17—N3—C10—C9	1.8 (3)	O2—C18—C23—C22	−174.6 (3)
C11—N3—C10—C9	−177.0 (2)	C21—C22—C23—C18	−0.1 (5)
C8—C9—C10—O1	179.7 (2)	Cl2^i—C24—Cl2—C24^i	0.0
S2—C9—C10—O1	−0.7 (4)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···Cg4	0.97	2.50	3.296 (7)	139
C24—H24B···Cg5	0.97	2.75	3.615 (8)	148