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The title compound, C24H24N6S3·0.5CHCl3 (TPSB·0.5CHCl3), crystallizes with one molecule of TPSB and half a solvent mol­ecule of CHCl3 in the asymmetric unit. The three 2-pyrimidinyl­thio­methyl groups attached to the central benzene ring adopt a cis,cis,cis conformation. The mol­ecule of TPSB is analogous to a `three-legged stool', and the dihedral angles between each of the three `legs' (2-pyrimidinyl rings) and the central benzene ring are 87.0 (5), 78.2 (3) and 97.1 (6)°, respectively, while the angles between the three `legs' are 41.1 (3), 91.3 (5) and 49.5 (7)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012680/ww6017sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012680/ww6017Isup2.hkl
Contains datablock I

CCDC reference: 193775

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.070
  • wR factor = 0.180
  • Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 50.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Bruker,1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,3,5-Tris(2-pyrimidinylthiomethyl)-2,4,6-Trimethylbenzene top
Crystal data top
C24H24N6S3·0.5CHCl3Dx = 1.273 Mg m3
Mr = 552.36Melting point = 468–469 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.957 (6) ÅCell parameters from 10845 reflections
b = 9.961 (3) Åθ = 2.4–24.7°
c = 16.335 (5) ŵ = 0.42 mm1
β = 110.885 (6)°T = 293 K
V = 2881.9 (16) Å3Needle, colorless
Z = 40.30 × 0.25 × 0.20 mm
F(000) = 1148
Data collection top
Bruker CCD area-detector
diffractometer
4853 independent reflections
Radiation source: fine-focus sealed tube1832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
φ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 229
Tmin = 0.884, Tmax = 0.921k = 1111
11025 measured reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.070 w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.180(Δ/σ)max = 0.007
S = 0.93Δρmax = 0.44 e Å3
4853 reflectionsΔρmin = 0.27 e Å3
334 parameters
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*/UeqOcc. (<1)
N10.6959 (3)1.1675 (5)0.0838 (3)0.0573 (13)
N20.7597 (3)1.3545 (6)0.0030 (4)0.0779 (16)
N30.8589 (3)0.4718 (6)0.4052 (3)0.0700 (15)
N40.9154 (3)0.6083 (5)0.5305 (4)0.0694 (15)
N50.4184 (3)0.9709 (5)0.3376 (3)0.0530 (12)
N60.4819 (3)1.1537 (5)0.4301 (3)0.0522 (12)
S10.73209 (10)1.16335 (16)0.08913 (10)0.0653 (5)
S20.83027 (10)0.73296 (16)0.39103 (12)0.0755 (6)
S30.54751 (9)1.06361 (15)0.32728 (10)0.0555 (5)
C10.6660 (3)0.9459 (5)0.1315 (3)0.0462 (14)
C20.7199 (3)0.8495 (6)0.1773 (4)0.0502 (14)
C30.7077 (3)0.7775 (6)0.2445 (4)0.0532 (15)
C40.6438 (3)0.8044 (5)0.2672 (3)0.0431 (13)
C50.5931 (3)0.9013 (5)0.2221 (3)0.0425 (13)
C60.6040 (3)0.9764 (5)0.1546 (3)0.0447 (14)
C70.7901 (4)0.8256 (7)0.1547 (5)0.084 (2)
H7A0.78890.88300.10700.127*
H7B0.79150.73350.13800.127*
H7C0.83430.84520.20490.127*
C80.6339 (3)0.7298 (6)0.3440 (4)0.0647 (17)
H8A0.58860.76000.35170.097*
H8B0.67650.74740.39640.097*
H8C0.63050.63520.33220.097*
C90.5508 (3)1.0872 (6)0.1111 (4)0.0580 (16)
H9A0.51161.09230.13550.087*
H9B0.52871.06980.04940.087*
H9C0.57771.17080.12060.087*
C100.6749 (4)1.0157 (6)0.0525 (4)0.0611 (16)
H10A0.62571.04060.01090.073*
H10B0.69860.95530.02350.073*
C110.7275 (3)1.2341 (6)0.0113 (4)0.0526 (15)
C120.6974 (4)1.2258 (7)0.1582 (4)0.0687 (18)
H12A0.67621.18210.21170.082*
C130.7307 (4)1.3502 (9)0.1542 (6)0.083 (2)
H13A0.73151.39150.20490.100*
C140.7615 (4)1.4098 (7)0.0768 (6)0.079 (2)
H14A0.78501.49260.07380.094*
C150.7621 (3)0.6686 (6)0.2910 (4)0.0595 (16)
H15A0.78790.63540.25330.071*
H15B0.73470.59450.30420.071*
C160.8711 (3)0.5890 (6)0.4464 (4)0.0556 (15)
C170.8901 (4)0.3643 (7)0.4518 (6)0.079 (2)
H17A0.88170.28070.42470.095*
C180.9351 (4)0.3731 (8)0.5398 (5)0.081 (2)
H18A0.95640.29760.57290.097*
C190.9462 (4)0.5005 (9)0.5752 (5)0.084 (2)
H19A0.97720.51050.63360.101*
C200.5234 (3)0.9298 (6)0.2458 (3)0.0504 (15)
H20A0.50860.84960.26940.060*
H20B0.48150.95720.19410.060*
C210.4735 (3)1.0585 (5)0.3674 (3)0.0436 (13)
C220.3676 (3)0.9747 (6)0.3770 (4)0.0617 (17)
H22A0.32830.91280.35960.074*
C230.3700 (4)1.0645 (6)0.4416 (4)0.0576 (16)
H23A0.33391.06500.46800.069*
C240.4283 (4)1.1523 (7)0.4644 (4)0.0607 (17)
H24A0.43081.21600.50700.073*
C250.9836 (6)0.6149 (9)0.1359 (6)0.044 (3)0.50
H25A0.96810.67400.08460.053*0.50
Cl10.9085 (2)0.5178 (3)0.1320 (3)0.1090 (16)0.50
Cl21.0176 (4)0.7115 (4)0.2275 (2)0.148 (2)0.50
Cl31.0550 (2)0.5069 (4)0.1294 (4)0.1197 (16)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.067 (3)0.062 (3)0.047 (3)0.004 (3)0.026 (3)0.006 (3)
N20.092 (4)0.061 (4)0.093 (4)0.012 (3)0.048 (4)0.003 (3)
N30.064 (4)0.055 (4)0.080 (4)0.000 (3)0.012 (3)0.001 (3)
N40.079 (4)0.057 (4)0.069 (4)0.002 (3)0.023 (3)0.005 (3)
N50.055 (3)0.064 (3)0.047 (3)0.010 (3)0.026 (3)0.000 (2)
N60.057 (3)0.056 (3)0.045 (3)0.005 (2)0.021 (3)0.004 (2)
S10.0890 (13)0.0625 (10)0.0526 (9)0.0215 (9)0.0353 (9)0.0058 (8)
S20.0734 (12)0.0470 (10)0.0864 (12)0.0010 (9)0.0043 (10)0.0088 (9)
S30.0570 (10)0.0622 (10)0.0579 (9)0.0088 (8)0.0335 (8)0.0119 (8)
C10.064 (4)0.042 (3)0.040 (3)0.014 (3)0.028 (3)0.009 (3)
C20.054 (4)0.047 (4)0.058 (4)0.002 (3)0.030 (3)0.007 (3)
C30.047 (4)0.051 (4)0.060 (4)0.005 (3)0.017 (3)0.009 (3)
C40.055 (4)0.041 (3)0.037 (3)0.001 (3)0.021 (3)0.005 (3)
C50.044 (3)0.045 (3)0.045 (3)0.001 (3)0.024 (3)0.010 (3)
C60.050 (4)0.049 (4)0.035 (3)0.001 (3)0.014 (3)0.000 (3)
C70.101 (5)0.089 (5)0.093 (5)0.019 (4)0.071 (5)0.004 (4)
C80.074 (4)0.062 (4)0.063 (4)0.007 (3)0.030 (3)0.014 (3)
C90.069 (4)0.057 (4)0.053 (3)0.001 (3)0.027 (3)0.005 (3)
C100.083 (5)0.056 (4)0.053 (3)0.012 (3)0.035 (3)0.009 (3)
C110.051 (4)0.044 (4)0.069 (4)0.005 (3)0.029 (3)0.002 (3)
C120.075 (5)0.077 (5)0.059 (4)0.020 (4)0.030 (4)0.008 (4)
C130.078 (5)0.085 (6)0.100 (6)0.016 (4)0.047 (5)0.038 (5)
C140.102 (6)0.058 (5)0.092 (6)0.004 (4)0.054 (5)0.022 (4)
C150.063 (4)0.052 (4)0.066 (4)0.003 (3)0.025 (3)0.007 (3)
C160.050 (4)0.047 (4)0.067 (4)0.005 (3)0.017 (3)0.010 (3)
C170.064 (5)0.053 (5)0.118 (7)0.000 (4)0.031 (5)0.002 (4)
C180.082 (6)0.060 (5)0.093 (6)0.002 (4)0.023 (5)0.015 (4)
C190.073 (5)0.079 (6)0.090 (5)0.000 (4)0.017 (4)0.006 (5)
C200.042 (3)0.055 (4)0.055 (3)0.005 (3)0.018 (3)0.002 (3)
C210.048 (4)0.043 (3)0.040 (3)0.004 (3)0.016 (3)0.000 (3)
C220.054 (4)0.064 (4)0.074 (4)0.002 (3)0.032 (4)0.016 (4)
C230.063 (4)0.063 (4)0.061 (4)0.011 (4)0.039 (3)0.002 (3)
C240.080 (5)0.065 (4)0.053 (4)0.011 (4)0.042 (4)0.004 (3)
C250.054 (7)0.023 (5)0.038 (6)0.011 (5)0.005 (5)0.015 (4)
Cl10.066 (2)0.047 (2)0.229 (5)0.0116 (17)0.070 (3)0.023 (3)
Cl20.274 (6)0.073 (3)0.041 (2)0.036 (3)0.012 (3)0.0050 (17)
Cl30.086 (3)0.083 (3)0.211 (5)0.024 (2)0.079 (3)0.032 (3)
Geometric parameters (Å, º) top
N1—C111.302 (7)C1—C101.527 (7)
N1—C121.357 (7)C2—C31.398 (8)
N2—C111.330 (7)C2—C71.523 (8)
N2—C141.336 (8)C3—C41.412 (7)
N3—C171.324 (8)C3—C151.503 (8)
N3—C161.326 (7)C4—C51.376 (7)
N4—C191.314 (8)C4—C81.526 (7)
N4—C161.343 (7)C5—C61.408 (7)
N5—C211.314 (7)C5—C201.531 (7)
N5—C221.337 (7)C6—C91.494 (7)
N6—C241.325 (7)C12—C131.381 (10)
N6—C211.362 (6)C13—C141.330 (10)
S1—C111.759 (6)C17—C181.389 (10)
S1—C101.798 (6)C18—C191.379 (10)
S2—C161.725 (6)C22—C231.372 (8)
S2—C151.802 (6)C23—C241.353 (8)
S3—C211.748 (6)C25—Cl21.700 (10)
S3—C201.823 (5)C25—Cl11.704 (11)
C1—C61.389 (7)C25—Cl31.762 (11)
C1—C21.407 (8)
C11—N1—C12116.5 (5)C5—C6—C9120.1 (5)
C11—N2—C14116.0 (6)C1—C10—S1109.1 (4)
C17—N3—C16117.3 (6)N1—C11—N2126.7 (6)
C19—N4—C16116.3 (6)N1—C11—S1119.8 (4)
C21—N5—C22114.7 (5)N2—C11—S1113.5 (5)
C24—N6—C21114.1 (5)N1—C12—C13119.8 (6)
C11—S1—C10101.2 (3)C14—C13—C12119.0 (7)
C16—S2—C15102.9 (3)C13—C14—N2122.0 (7)
C21—S3—C20103.1 (3)C3—C15—S2110.0 (4)
C6—C1—C2121.9 (5)N3—C16—N4125.3 (6)
C6—C1—C10119.2 (5)N3—C16—S2120.1 (5)
C2—C1—C10118.8 (5)N4—C16—S2114.6 (5)
C3—C2—C1118.4 (5)N3—C17—C18121.8 (7)
C3—C2—C7120.9 (6)C19—C18—C17116.0 (7)
C1—C2—C7120.7 (5)N4—C19—C18123.2 (7)
C2—C3—C4120.4 (5)C5—C20—S3107.8 (3)
C2—C3—C15119.4 (5)N5—C21—N6127.3 (5)
C4—C3—C15120.2 (5)N5—C21—S3121.2 (4)
C5—C4—C3119.6 (5)N6—C21—S3111.5 (4)
C5—C4—C8121.0 (5)N5—C22—C23123.8 (6)
C3—C4—C8119.4 (5)C24—C23—C22115.7 (5)
C4—C5—C6121.5 (5)N6—C24—C23124.4 (6)
C4—C5—C20119.8 (5)Cl2—C25—Cl1113.9 (7)
C6—C5—C20118.7 (5)Cl2—C25—Cl3109.9 (6)
C1—C6—C5118.1 (5)Cl1—C25—Cl3107.5 (5)
C1—C6—C9121.8 (5)
C6—C1—C2—C33.8 (8)C10—S1—C11—N2173.4 (4)
C10—C1—C2—C3174.3 (5)C11—N1—C12—C130.8 (8)
C6—C1—C2—C7175.5 (5)N1—C12—C13—C140.8 (10)
C10—C1—C2—C76.3 (8)C12—C13—C14—N21.6 (11)
C1—C2—C3—C41.9 (8)C11—N2—C14—C132.2 (10)
C7—C2—C3—C4177.4 (5)C2—C3—C15—S296.7 (5)
C1—C2—C3—C15176.6 (5)C4—C3—C15—S284.8 (5)
C7—C2—C3—C154.1 (8)C16—S2—C15—C3165.7 (4)
C2—C3—C4—C50.7 (8)C17—N3—C16—N43.2 (9)
C15—C3—C4—C5177.8 (5)C17—N3—C16—S2178.2 (5)
C2—C3—C4—C8176.7 (5)C19—N4—C16—N32.6 (9)
C15—C3—C4—C84.8 (7)C19—N4—C16—S2178.7 (5)
C3—C4—C5—C61.2 (8)C15—S2—C16—N312.3 (6)
C8—C4—C5—C6176.1 (5)C15—S2—C16—N4169.0 (5)
C3—C4—C5—C20179.3 (5)C16—N3—C17—C181.2 (10)
C8—C4—C5—C203.3 (7)N3—C17—C18—C191.1 (10)
C2—C1—C6—C54.3 (8)C16—N4—C19—C180.0 (10)
C10—C1—C6—C5173.8 (4)C17—C18—C19—N41.7 (11)
C2—C1—C6—C9174.4 (5)C4—C5—C20—S391.7 (5)
C10—C1—C6—C97.4 (7)C6—C5—C20—S387.8 (5)
C4—C5—C6—C13.0 (7)C21—S3—C20—C5166.3 (4)
C20—C5—C6—C1177.6 (4)C22—N5—C21—N63.0 (8)
C4—C5—C6—C9175.8 (5)C22—N5—C21—S3177.2 (4)
C20—C5—C6—C93.7 (7)C24—N6—C21—N51.7 (8)
C6—C1—C10—S192.7 (5)C24—N6—C21—S3178.5 (4)
C2—C1—C10—S189.0 (5)C20—S3—C21—N50.1 (5)
C11—S1—C10—C1174.9 (4)C20—S3—C21—N6179.8 (4)
C12—N1—C11—N21.6 (9)C21—N5—C22—C232.0 (8)
C12—N1—C11—S1177.1 (4)N5—C22—C23—C240.0 (8)
C14—N2—C11—N12.3 (9)C21—N6—C24—C230.8 (8)
C14—N2—C11—S1176.5 (5)C22—C23—C24—N61.5 (9)
C10—S1—C11—N17.6 (5)
 

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