Download citation
Download citation
link to html
In the title compound, C23H14ClN3O2S2·C6H5ClO, the mean plane of the thia­zolopyrimidine fragment makes dihedral angles of 64.26 (11), 77.70 (10) and 49.70 (18)° with the two attached phenyl rings and the 4-chloro­phen­oxy fragment. The crystal packing is stabilized by inter­molecular O—H...O and intra­molecular C—H...N hydrogen bonds, as well as by weak π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052615/wn2100sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052615/wn2100Isup2.hkl
Contains datablock I

CCDC reference: 634070

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.140
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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 top

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 4-chlorophenol solvate top
Crystal data top
C23H14ClN3O2S2·C6H5ClOZ = 2
Mr = 592.49F(000) = 608
Triclinic, P1Dx = 1.434 Mg m3
a = 10.1348 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.5389 (13) ÅCell parameters from 3766 reflections
c = 13.6575 (15) Åθ = 2.2–27.8°
α = 113.048 (2)°µ = 0.43 mm1
β = 95.896 (2)°T = 292 K
γ = 105.972 (2)°Block, colourless
V = 1372.4 (3) Å30.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4250 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 26.0°, θmin = 1.7°
φ and ω scansh = 128
7829 measured reflectionsk = 1412
5302 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0761P)2]
where P = (Fo2 + 2Fc2)/3
5302 reflections(Δ/σ)max = 0.001
356 parametersΔρmax = 0.35 e Å3
1 restraintΔρmin = 0.45 e Å3
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
S20.19892 (7)1.05543 (6)1.07799 (5)0.05180 (18)
Cl10.16603 (7)1.15170 (6)0.35219 (5)0.05797 (19)
S10.14058 (8)1.31175 (6)1.16484 (5)0.0607 (2)
Cl20.33952 (10)0.65670 (10)0.40319 (8)0.0971 (3)
O20.20147 (17)0.86939 (14)0.62438 (12)0.0485 (4)
N20.17898 (18)1.02628 (17)0.78372 (14)0.0409 (4)
N30.23295 (18)0.83517 (16)0.77446 (14)0.0407 (4)
C170.2037 (2)0.9164 (2)0.73104 (17)0.0399 (4)
N10.15915 (18)1.17214 (16)0.95743 (14)0.0418 (4)
O10.26890 (19)0.79254 (15)0.92294 (13)0.0577 (4)
C80.1828 (2)1.0568 (2)0.88960 (17)0.0402 (4)
C180.1879 (2)0.9443 (2)0.56643 (16)0.0395 (5)
C200.0916 (2)0.9365 (2)0.39652 (17)0.0432 (5)
H200.03190.89030.32670.052*
C210.1728 (2)1.0698 (2)0.43530 (17)0.0421 (5)
C90.2077 (2)0.9834 (2)0.94257 (17)0.0443 (5)
C220.2593 (2)1.1406 (2)0.53921 (17)0.0437 (5)
H220.31231.23080.56430.052*
C190.1000 (2)0.8726 (2)0.46232 (17)0.0439 (5)
H190.04720.78230.43700.053*
C60.1422 (2)1.2689 (2)0.91985 (17)0.0437 (5)
C230.2677 (2)1.0784 (2)0.60584 (17)0.0424 (5)
H230.32591.12560.67620.051*
C100.2382 (2)0.8647 (2)0.88544 (17)0.0439 (5)
C110.2714 (2)0.7205 (2)0.70932 (17)0.0432 (5)
C70.1628 (2)1.1874 (2)1.06322 (18)0.0454 (5)
C140.3483 (4)0.5086 (3)0.5871 (2)0.0695 (8)
H140.37440.43710.54460.083*
C160.1681 (3)0.6027 (2)0.6344 (2)0.0577 (6)
H160.07330.59470.62540.069*
C280.4172 (3)0.9327 (3)0.2913 (2)0.0614 (6)
H280.43341.02420.31890.074*
C290.3922 (3)0.8685 (3)0.3568 (2)0.0624 (7)
H290.39040.91670.42920.075*
C120.4108 (3)0.7322 (2)0.7251 (2)0.0553 (6)
H120.47930.81170.77700.066*
C10.2524 (3)1.3344 (3)0.8879 (2)0.0653 (7)
H10.33731.31820.89220.078*
C50.0170 (3)1.2932 (2)0.9143 (2)0.0571 (6)
H50.05711.24820.93550.069*
C270.4180 (2)0.8595 (2)0.1834 (2)0.0548 (6)
C260.3946 (3)0.7242 (3)0.1419 (2)0.0633 (7)
H260.39460.67570.06920.076*
C150.2087 (4)0.4961 (2)0.5726 (2)0.0704 (8)
H150.14070.41590.52130.084*
C240.3699 (3)0.7338 (3)0.3166 (2)0.0605 (6)
C20.2342 (4)1.4245 (3)0.8494 (3)0.0848 (9)
H20.30691.46850.82650.102*
C130.4494 (3)0.6244 (3)0.6628 (3)0.0708 (8)
H130.54390.63130.67290.085*
C30.1106 (4)1.4495 (3)0.8447 (3)0.0842 (10)
H30.09981.51100.81920.101*
C40.0023 (4)1.3848 (3)0.8772 (3)0.0766 (8)
H40.08161.40280.87410.092*
C250.3709 (3)0.6600 (3)0.2099 (2)0.0692 (7)
H250.35610.56870.18330.083*
O30.4481 (2)0.9279 (2)0.12121 (19)0.0788 (6)
H3A0.413 (5)0.880 (3)0.0550 (11)0.145 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0777 (4)0.0483 (3)0.0374 (3)0.0255 (3)0.0180 (3)0.0231 (2)
Cl10.0773 (4)0.0627 (4)0.0472 (3)0.0260 (3)0.0167 (3)0.0355 (3)
S10.0915 (5)0.0509 (4)0.0438 (3)0.0307 (3)0.0273 (3)0.0179 (3)
Cl20.1132 (7)0.1155 (7)0.0947 (6)0.0395 (5)0.0438 (5)0.0730 (6)
O20.0767 (10)0.0463 (8)0.0375 (8)0.0338 (8)0.0207 (7)0.0230 (7)
N20.0551 (10)0.0400 (9)0.0366 (9)0.0231 (8)0.0152 (8)0.0201 (7)
N30.0532 (10)0.0367 (9)0.0381 (9)0.0186 (8)0.0107 (8)0.0201 (8)
C170.0482 (11)0.0396 (10)0.0383 (11)0.0182 (9)0.0127 (9)0.0207 (9)
N10.0543 (10)0.0388 (9)0.0372 (9)0.0195 (8)0.0154 (8)0.0180 (7)
O10.0910 (12)0.0493 (9)0.0465 (9)0.0328 (8)0.0130 (8)0.0294 (8)
C80.0474 (11)0.0364 (10)0.0377 (11)0.0144 (9)0.0112 (9)0.0170 (9)
C180.0495 (12)0.0464 (11)0.0365 (10)0.0273 (9)0.0181 (9)0.0229 (9)
C200.0498 (12)0.0483 (12)0.0316 (10)0.0187 (9)0.0105 (9)0.0161 (9)
C210.0503 (12)0.0484 (12)0.0412 (11)0.0254 (10)0.0185 (9)0.0256 (10)
C90.0578 (13)0.0431 (11)0.0355 (11)0.0182 (10)0.0122 (9)0.0198 (9)
C220.0487 (12)0.0425 (11)0.0431 (12)0.0142 (9)0.0134 (9)0.0223 (9)
C190.0517 (12)0.0399 (11)0.0404 (11)0.0187 (9)0.0148 (9)0.0149 (9)
C60.0600 (13)0.0371 (10)0.0381 (11)0.0200 (9)0.0168 (9)0.0172 (9)
C230.0446 (11)0.0458 (11)0.0373 (11)0.0180 (9)0.0081 (9)0.0177 (9)
C100.0559 (13)0.0384 (11)0.0391 (11)0.0152 (9)0.0101 (9)0.0196 (9)
C110.0617 (14)0.0343 (10)0.0401 (11)0.0198 (9)0.0138 (10)0.0201 (9)
C70.0543 (13)0.0422 (11)0.0412 (11)0.0148 (9)0.0163 (9)0.0199 (9)
C140.108 (2)0.0500 (15)0.0765 (19)0.0433 (15)0.0446 (17)0.0368 (14)
C160.0672 (15)0.0438 (13)0.0572 (15)0.0157 (11)0.0119 (12)0.0202 (11)
C280.0560 (14)0.0596 (15)0.0695 (17)0.0266 (12)0.0113 (12)0.0256 (13)
C290.0531 (14)0.0753 (17)0.0594 (16)0.0269 (12)0.0196 (12)0.0253 (14)
C120.0597 (15)0.0469 (13)0.0632 (15)0.0222 (11)0.0164 (12)0.0251 (12)
C10.0805 (18)0.0556 (14)0.0756 (18)0.0279 (13)0.0371 (15)0.0370 (14)
C50.0663 (15)0.0523 (13)0.0574 (15)0.0273 (12)0.0161 (12)0.0238 (12)
C270.0485 (13)0.0582 (14)0.0563 (14)0.0167 (11)0.0030 (11)0.0273 (12)
C260.0692 (16)0.0601 (15)0.0490 (14)0.0158 (12)0.0092 (12)0.0181 (12)
C150.103 (2)0.0389 (13)0.0620 (17)0.0190 (13)0.0189 (15)0.0185 (12)
C240.0570 (15)0.0722 (17)0.0625 (16)0.0230 (12)0.0192 (12)0.0378 (14)
C20.129 (3)0.0631 (18)0.083 (2)0.0315 (18)0.051 (2)0.0478 (17)
C130.0803 (18)0.0656 (17)0.089 (2)0.0422 (15)0.0370 (16)0.0411 (16)
C30.146 (3)0.0599 (17)0.0658 (19)0.051 (2)0.0288 (19)0.0354 (15)
C40.099 (2)0.0672 (17)0.0721 (19)0.0479 (16)0.0100 (16)0.0288 (15)
C250.0768 (18)0.0552 (15)0.0718 (18)0.0158 (13)0.0234 (14)0.0274 (14)
O30.0941 (15)0.0707 (13)0.0658 (13)0.0159 (11)0.0032 (11)0.0365 (11)
Geometric parameters (Å, º) top
S2—C91.729 (2)C11—C161.378 (3)
S2—C71.739 (2)C14—C131.361 (4)
Cl1—C211.745 (2)C14—C151.367 (4)
S1—C71.649 (2)C14—H140.9300
Cl2—C241.741 (3)C16—C151.390 (4)
O2—C171.336 (2)C16—H160.9300
O2—C181.404 (2)C28—C291.370 (4)
N2—C171.299 (3)C28—C271.384 (4)
N2—C81.341 (3)C28—H280.9300
N3—C171.367 (2)C29—C241.372 (4)
N3—C101.409 (3)C29—H290.9300
N3—C111.458 (3)C12—C131.390 (3)
N1—C71.381 (3)C12—H120.9300
N1—C81.394 (3)C1—C21.381 (4)
N1—C61.441 (3)C1—H10.9300
O1—C101.224 (2)C5—C41.373 (4)
C8—C91.365 (3)C5—H50.9300
C18—C231.381 (3)C27—O31.371 (3)
C18—C191.383 (3)C27—C261.376 (3)
C20—C191.377 (3)C26—C251.399 (4)
C20—C211.378 (3)C26—H260.9300
C20—H200.9300C15—H150.9300
C21—C221.376 (3)C24—C251.373 (4)
C9—C101.423 (3)C2—C31.361 (5)
C22—C231.370 (3)C2—H20.9300
C22—H220.9300C13—H130.9300
C19—H190.9300C3—C41.367 (5)
C6—C51.374 (3)C3—H30.9300
C6—C11.380 (3)C4—H40.9300
C23—H230.9300C25—H250.9300
C11—C121.368 (3)O3—H3A0.827 (9)
C9—S2—C791.45 (10)C13—C14—H14119.6
C17—O2—C18121.33 (15)C15—C14—H14119.6
C17—N2—C8113.87 (17)C11—C16—C15118.6 (2)
C17—N3—C10121.56 (17)C11—C16—H16120.7
C17—N3—C11120.76 (17)C15—C16—H16120.7
C10—N3—C11117.49 (16)C29—C28—C27119.2 (2)
N2—C17—O2121.99 (17)C29—C28—H28120.4
N2—C17—N3125.90 (19)C27—C28—H28120.4
O2—C17—N3112.11 (16)C28—C29—C24120.5 (3)
C7—N1—C8113.81 (17)C28—C29—H29119.7
C7—N1—C6124.39 (17)C24—C29—H29119.7
C8—N1—C6121.68 (17)C11—C12—C13119.5 (2)
N2—C8—C9126.23 (19)C11—C12—H12120.3
N2—C8—N1120.83 (18)C13—C12—H12120.3
C9—C8—N1112.93 (18)C6—C1—C2118.6 (3)
C23—C18—C19121.53 (19)C6—C1—H1120.7
C23—C18—O2122.35 (18)C2—C1—H1120.7
C19—C18—O2115.82 (18)C4—C5—C6119.3 (3)
C19—C20—C21119.21 (19)C4—C5—H5120.3
C19—C20—H20120.4C6—C5—H5120.3
C21—C20—H20120.4O3—C27—C26121.6 (2)
C22—C21—C20121.15 (19)O3—C27—C28117.6 (2)
C22—C21—Cl1118.97 (17)C26—C27—C28120.8 (2)
C20—C21—Cl1119.88 (16)C27—C26—C25119.6 (3)
C8—C9—C10119.83 (19)C27—C26—H26120.2
C8—C9—S2111.64 (16)C25—C26—H26120.2
C10—C9—S2128.53 (16)C14—C15—C16120.2 (3)
C23—C22—C21120.2 (2)C14—C15—H15119.9
C23—C22—H22119.9C16—C15—H15119.9
C21—C22—H22119.9C29—C24—C25121.0 (2)
C20—C19—C18119.23 (19)C29—C24—Cl2118.9 (2)
C20—C19—H19120.4C25—C24—Cl2120.1 (2)
C18—C19—H19120.4C3—C2—C1120.5 (3)
C5—C6—C1120.9 (2)C3—C2—H2119.7
C5—C6—N1120.2 (2)C1—C2—H2119.7
C1—C6—N1119.0 (2)C14—C13—C12119.7 (3)
C22—C23—C18118.67 (19)C14—C13—H13120.1
C22—C23—H23120.7C12—C13—H13120.1
C18—C23—H23120.7C2—C3—C4120.4 (3)
O1—C10—N3120.16 (19)C2—C3—H3119.8
O1—C10—C9127.3 (2)C4—C3—H3119.8
N3—C10—C9112.56 (17)C3—C4—C5120.2 (3)
C12—C11—C16121.2 (2)C3—C4—H4119.9
C12—C11—N3118.74 (19)C5—C4—H4119.9
C16—C11—N3120.1 (2)C24—C25—C26118.9 (3)
N1—C7—S1126.88 (16)C24—C25—H25120.5
N1—C7—S2110.15 (15)C26—C25—H25120.5
S1—C7—S2122.95 (13)C27—O3—H3A113 (3)
C13—C14—C15120.8 (2)
C8—N2—C17—O2178.71 (18)C8—C9—C10—O1176.4 (2)
C8—N2—C17—N30.6 (3)S2—C9—C10—O12.6 (4)
C18—O2—C17—N27.3 (3)C8—C9—C10—N32.3 (3)
C18—O2—C17—N3173.33 (17)S2—C9—C10—N3178.69 (16)
C10—N3—C17—N20.4 (3)C17—N3—C11—C12101.0 (2)
C11—N3—C17—N2174.46 (19)C10—N3—C11—C1274.1 (3)
C10—N3—C17—O2178.94 (17)C17—N3—C11—C1679.7 (3)
C11—N3—C17—O26.2 (3)C10—N3—C11—C16105.2 (2)
C17—N2—C8—C90.9 (3)C8—N1—C7—S1179.51 (16)
C17—N2—C8—N1179.66 (18)C6—N1—C7—S13.5 (3)
C7—N1—C8—N2178.30 (18)C8—N1—C7—S20.8 (2)
C6—N1—C8—N25.6 (3)C6—N1—C7—S2175.22 (16)
C7—N1—C8—C91.2 (3)C9—S2—C7—N10.14 (16)
C6—N1—C8—C9174.90 (18)C9—S2—C7—S1178.93 (16)
C17—O2—C18—C2347.2 (3)C12—C11—C16—C151.6 (4)
C17—O2—C18—C19139.1 (2)N3—C11—C16—C15179.1 (2)
C19—C20—C21—C221.5 (3)C27—C28—C29—C240.7 (4)
C19—C20—C21—Cl1178.82 (16)C16—C11—C12—C131.4 (4)
N2—C8—C9—C102.5 (3)N3—C11—C12—C13179.3 (2)
N1—C8—C9—C10178.05 (19)C5—C6—C1—C20.4 (4)
N2—C8—C9—S2178.40 (17)N1—C6—C1—C2178.4 (2)
N1—C8—C9—S21.1 (2)C1—C6—C5—C40.5 (4)
C7—S2—C9—C80.54 (17)N1—C6—C5—C4179.3 (2)
C7—S2—C9—C10178.5 (2)C29—C28—C27—O3177.8 (2)
C20—C21—C22—C230.9 (3)C29—C28—C27—C260.2 (4)
Cl1—C21—C22—C23179.38 (16)O3—C27—C26—C25177.0 (2)
C21—C20—C19—C181.1 (3)C28—C27—C26—C250.5 (4)
C23—C18—C19—C200.1 (3)C13—C14—C15—C160.9 (4)
O2—C18—C19—C20173.95 (18)C11—C16—C15—C140.4 (4)
C7—N1—C6—C567.2 (3)C28—C29—C24—C250.5 (4)
C8—N1—C6—C5117.1 (2)C28—C29—C24—Cl2179.65 (19)
C7—N1—C6—C1114.0 (3)C6—C1—C2—C31.0 (5)
C8—N1—C6—C161.7 (3)C15—C14—C13—C121.2 (4)
C21—C22—C23—C180.1 (3)C11—C12—C13—C140.0 (4)
C19—C18—C23—C220.4 (3)C1—C2—C3—C40.6 (5)
O2—C18—C23—C22172.98 (18)C2—C3—C4—C50.4 (5)
C17—N3—C10—O1177.74 (19)C6—C5—C4—C30.9 (4)
C11—N3—C10—O12.7 (3)C29—C24—C25—C260.3 (4)
C17—N3—C10—C91.1 (3)Cl2—C24—C25—C26179.6 (2)
C11—N3—C10—C9176.11 (18)C27—C26—C25—C240.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N20.932.552.893 (3)102
O3—H3A···O1i0.83 (1)1.90 (2)2.681 (3)156 (4)
Symmetry code: (i) x, y, z1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds