2,4,6-Tri­methyl-1,3,5-tris(2-pyrimidinyl­thio­methyl)­benzene chloroform hemisolvate

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.

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


 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

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Computing details

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

Crystal data

C24H24N6S3·0.5CHCl3	Dx = 1.273 Mg m^−3
Mr = 552.36	Melting point = 468–469 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.957 (6) Å	Cell parameters from 10845 reflections
b = 9.961 (3) Å	θ = 2.4–24.7°
c = 16.335 (5) Å	µ = 0.42 mm^−1
β = 110.885 (6)°	T = 293 K
V = 2881.9 (16) Å^3	Needle, colorless
Z = 4	0.30 × 0.25 × 0.20 mm
F(000) = 1148

Data collection

Bruker CCD area-detector diffractometer	4853 independent reflections
Radiation source: fine-focus sealed tube	1832 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −22→9
Tmin = 0.884, Tmax = 0.921	k = −11→11
11025 measured reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.070	w = 1/[σ^2(Fo^2) + (0.06P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.180	(Δ/σ)max = 0.007
S = 0.93	Δρmax = 0.44 e Å^−3
4853 reflections	Δρmin = −0.27 e Å^−3
334 parameters

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)
N1	0.6959 (3)	1.1675 (5)	−0.0838 (3)	0.0573 (13)
N2	0.7597 (3)	1.3545 (6)	−0.0030 (4)	0.0779 (16)
N3	0.8589 (3)	0.4718 (6)	0.4052 (3)	0.0700 (15)
N4	0.9154 (3)	0.6083 (5)	0.5305 (4)	0.0694 (15)
N5	0.4184 (3)	0.9709 (5)	0.3376 (3)	0.0530 (12)
N6	0.4819 (3)	1.1537 (5)	0.4301 (3)	0.0522 (12)
S1	0.73209 (10)	1.16335 (16)	0.08913 (10)	0.0653 (5)
S2	0.83027 (10)	0.73296 (16)	0.39103 (12)	0.0755 (6)
S3	0.54751 (9)	1.06361 (15)	0.32728 (10)	0.0555 (5)
C1	0.6660 (3)	0.9459 (5)	0.1315 (3)	0.0462 (14)
C2	0.7199 (3)	0.8495 (6)	0.1773 (4)	0.0502 (14)
C3	0.7077 (3)	0.7775 (6)	0.2445 (4)	0.0532 (15)
C4	0.6438 (3)	0.8044 (5)	0.2672 (3)	0.0431 (13)
C5	0.5931 (3)	0.9013 (5)	0.2221 (3)	0.0425 (13)
C6	0.6040 (3)	0.9764 (5)	0.1546 (3)	0.0447 (14)
C7	0.7901 (4)	0.8256 (7)	0.1547 (5)	0.084 (2)
H7A	0.7889	0.8830	0.1070	0.127*
H7B	0.7915	0.7335	0.1380	0.127*
H7C	0.8343	0.8452	0.2049	0.127*
C8	0.6339 (3)	0.7298 (6)	0.3440 (4)	0.0647 (17)
H8A	0.5886	0.7600	0.3517	0.097*
H8B	0.6765	0.7474	0.3964	0.097*
H8C	0.6305	0.6352	0.3322	0.097*
C9	0.5508 (3)	1.0872 (6)	0.1111 (4)	0.0580 (16)
H9A	0.5116	1.0923	0.1355	0.087*
H9B	0.5287	1.0698	0.0494	0.087*
H9C	0.5777	1.1708	0.1206	0.087*
C10	0.6749 (4)	1.0157 (6)	0.0525 (4)	0.0611 (16)
H10A	0.6257	1.0406	0.0109	0.073*
H10B	0.6986	0.9553	0.0235	0.073*
C11	0.7275 (3)	1.2341 (6)	−0.0113 (4)	0.0526 (15)
C12	0.6974 (4)	1.2258 (7)	−0.1582 (4)	0.0687 (18)
H12A	0.6762	1.1821	−0.2117	0.082*
C13	0.7307 (4)	1.3502 (9)	−0.1542 (6)	0.083 (2)
H13A	0.7315	1.3915	−0.2049	0.100*
C14	0.7615 (4)	1.4098 (7)	−0.0768 (6)	0.079 (2)
H14A	0.7850	1.4926	−0.0738	0.094*
C15	0.7621 (3)	0.6686 (6)	0.2910 (4)	0.0595 (16)
H15A	0.7879	0.6354	0.2533	0.071*
H15B	0.7347	0.5945	0.3042	0.071*
C16	0.8711 (3)	0.5890 (6)	0.4464 (4)	0.0556 (15)
C17	0.8901 (4)	0.3643 (7)	0.4518 (6)	0.079 (2)
H17A	0.8817	0.2807	0.4247	0.095*
C18	0.9351 (4)	0.3731 (8)	0.5398 (5)	0.081 (2)
H18A	0.9564	0.2976	0.5729	0.097*
C19	0.9462 (4)	0.5005 (9)	0.5752 (5)	0.084 (2)
H19A	0.9772	0.5105	0.6336	0.101*
C20	0.5234 (3)	0.9298 (6)	0.2458 (3)	0.0504 (15)
H20A	0.5086	0.8496	0.2694	0.060*
H20B	0.4815	0.9572	0.1941	0.060*
C21	0.4735 (3)	1.0585 (5)	0.3674 (3)	0.0436 (13)
C22	0.3676 (3)	0.9747 (6)	0.3770 (4)	0.0617 (17)
H22A	0.3283	0.9128	0.3596	0.074*
C23	0.3700 (4)	1.0645 (6)	0.4416 (4)	0.0576 (16)
H23A	0.3339	1.0650	0.4680	0.069*
C24	0.4283 (4)	1.1523 (7)	0.4644 (4)	0.0607 (17)
H24A	0.4308	1.2160	0.5070	0.073*
C25	0.9836 (6)	0.6149 (9)	0.1359 (6)	0.044 (3)	0.50
H25A	0.9681	0.6740	0.0846	0.053*	0.50
Cl1	0.9085 (2)	0.5178 (3)	0.1320 (3)	0.1090 (16)	0.50
Cl2	1.0176 (4)	0.7115 (4)	0.2275 (2)	0.148 (2)	0.50
Cl3	1.0550 (2)	0.5069 (4)	0.1294 (4)	0.1197 (16)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.067 (3)	0.062 (3)	0.047 (3)	0.004 (3)	0.026 (3)	0.006 (3)
N2	0.092 (4)	0.061 (4)	0.093 (4)	−0.012 (3)	0.048 (4)	−0.003 (3)
N3	0.064 (4)	0.055 (4)	0.080 (4)	0.000 (3)	0.012 (3)	−0.001 (3)
N4	0.079 (4)	0.057 (4)	0.069 (4)	0.002 (3)	0.023 (3)	−0.005 (3)
N5	0.055 (3)	0.064 (3)	0.047 (3)	−0.010 (3)	0.026 (3)	0.000 (2)
N6	0.057 (3)	0.056 (3)	0.045 (3)	0.005 (2)	0.021 (3)	−0.004 (2)
S1	0.0890 (13)	0.0625 (10)	0.0526 (9)	−0.0215 (9)	0.0353 (9)	−0.0058 (8)
S2	0.0734 (12)	0.0470 (10)	0.0864 (12)	−0.0010 (9)	0.0043 (10)	−0.0088 (9)
S3	0.0570 (10)	0.0622 (10)	0.0579 (9)	−0.0088 (8)	0.0335 (8)	−0.0119 (8)
C1	0.064 (4)	0.042 (3)	0.040 (3)	−0.014 (3)	0.028 (3)	−0.009 (3)
C2	0.054 (4)	0.047 (4)	0.058 (4)	−0.002 (3)	0.030 (3)	−0.007 (3)
C3	0.047 (4)	0.051 (4)	0.060 (4)	−0.005 (3)	0.017 (3)	−0.009 (3)
C4	0.055 (4)	0.041 (3)	0.037 (3)	−0.001 (3)	0.021 (3)	−0.005 (3)
C5	0.044 (3)	0.045 (3)	0.045 (3)	−0.001 (3)	0.024 (3)	−0.010 (3)
C6	0.050 (4)	0.049 (4)	0.035 (3)	0.001 (3)	0.014 (3)	0.000 (3)
C7	0.101 (5)	0.089 (5)	0.093 (5)	0.019 (4)	0.071 (5)	−0.004 (4)
C8	0.074 (4)	0.062 (4)	0.063 (4)	−0.007 (3)	0.030 (3)	0.014 (3)
C9	0.069 (4)	0.057 (4)	0.053 (3)	0.001 (3)	0.027 (3)	0.005 (3)
C10	0.083 (5)	0.056 (4)	0.053 (3)	−0.012 (3)	0.035 (3)	−0.009 (3)
C11	0.051 (4)	0.044 (4)	0.069 (4)	−0.005 (3)	0.029 (3)	0.002 (3)
C12	0.075 (5)	0.077 (5)	0.059 (4)	0.020 (4)	0.030 (4)	0.008 (4)
C13	0.078 (5)	0.085 (6)	0.100 (6)	0.016 (4)	0.047 (5)	0.038 (5)
C14	0.102 (6)	0.058 (5)	0.092 (6)	−0.004 (4)	0.054 (5)	0.022 (4)
C15	0.063 (4)	0.052 (4)	0.066 (4)	0.003 (3)	0.025 (3)	−0.007 (3)
C16	0.050 (4)	0.047 (4)	0.067 (4)	−0.005 (3)	0.017 (3)	−0.010 (3)
C17	0.064 (5)	0.053 (5)	0.118 (7)	0.000 (4)	0.031 (5)	−0.002 (4)
C18	0.082 (6)	0.060 (5)	0.093 (6)	0.002 (4)	0.023 (5)	0.015 (4)
C19	0.073 (5)	0.079 (6)	0.090 (5)	0.000 (4)	0.017 (4)	0.006 (5)
C20	0.042 (3)	0.055 (4)	0.055 (3)	0.005 (3)	0.018 (3)	−0.002 (3)
C21	0.048 (4)	0.043 (3)	0.040 (3)	−0.004 (3)	0.016 (3)	0.000 (3)
C22	0.054 (4)	0.064 (4)	0.074 (4)	−0.002 (3)	0.032 (4)	0.016 (4)
C23	0.063 (4)	0.063 (4)	0.061 (4)	0.011 (4)	0.039 (3)	0.002 (3)
C24	0.080 (5)	0.065 (4)	0.053 (4)	0.011 (4)	0.042 (4)	0.004 (3)
C25	0.054 (7)	0.023 (5)	0.038 (6)	0.011 (5)	−0.005 (5)	0.015 (4)
Cl1	0.066 (2)	0.047 (2)	0.229 (5)	0.0116 (17)	0.070 (3)	0.023 (3)
Cl2	0.274 (6)	0.073 (3)	0.041 (2)	−0.036 (3)	−0.012 (3)	0.0050 (17)
Cl3	0.086 (3)	0.083 (3)	0.211 (5)	0.024 (2)	0.079 (3)	0.032 (3)

Geometric parameters (Å, º)

N1—C11	1.302 (7)	C1—C10	1.527 (7)
N1—C12	1.357 (7)	C2—C3	1.398 (8)
N2—C11	1.330 (7)	C2—C7	1.523 (8)
N2—C14	1.336 (8)	C3—C4	1.412 (7)
N3—C17	1.324 (8)	C3—C15	1.503 (8)
N3—C16	1.326 (7)	C4—C5	1.376 (7)
N4—C19	1.314 (8)	C4—C8	1.526 (7)
N4—C16	1.343 (7)	C5—C6	1.408 (7)
N5—C21	1.314 (7)	C5—C20	1.531 (7)
N5—C22	1.337 (7)	C6—C9	1.494 (7)
N6—C24	1.325 (7)	C12—C13	1.381 (10)
N6—C21	1.362 (6)	C13—C14	1.330 (10)
S1—C11	1.759 (6)	C17—C18	1.389 (10)
S1—C10	1.798 (6)	C18—C19	1.379 (10)
S2—C16	1.725 (6)	C22—C23	1.372 (8)
S2—C15	1.802 (6)	C23—C24	1.353 (8)
S3—C21	1.748 (6)	C25—Cl2	1.700 (10)
S3—C20	1.823 (5)	C25—Cl1	1.704 (11)
C1—C6	1.389 (7)	C25—Cl3	1.762 (11)
C1—C2	1.407 (8)
C11—N1—C12	116.5 (5)	C5—C6—C9	120.1 (5)
C11—N2—C14	116.0 (6)	C1—C10—S1	109.1 (4)
C17—N3—C16	117.3 (6)	N1—C11—N2	126.7 (6)
C19—N4—C16	116.3 (6)	N1—C11—S1	119.8 (4)
C21—N5—C22	114.7 (5)	N2—C11—S1	113.5 (5)
C24—N6—C21	114.1 (5)	N1—C12—C13	119.8 (6)
C11—S1—C10	101.2 (3)	C14—C13—C12	119.0 (7)
C16—S2—C15	102.9 (3)	C13—C14—N2	122.0 (7)
C21—S3—C20	103.1 (3)	C3—C15—S2	110.0 (4)
C6—C1—C2	121.9 (5)	N3—C16—N4	125.3 (6)
C6—C1—C10	119.2 (5)	N3—C16—S2	120.1 (5)
C2—C1—C10	118.8 (5)	N4—C16—S2	114.6 (5)
C3—C2—C1	118.4 (5)	N3—C17—C18	121.8 (7)
C3—C2—C7	120.9 (6)	C19—C18—C17	116.0 (7)
C1—C2—C7	120.7 (5)	N4—C19—C18	123.2 (7)
C2—C3—C4	120.4 (5)	C5—C20—S3	107.8 (3)
C2—C3—C15	119.4 (5)	N5—C21—N6	127.3 (5)
C4—C3—C15	120.2 (5)	N5—C21—S3	121.2 (4)
C5—C4—C3	119.6 (5)	N6—C21—S3	111.5 (4)
C5—C4—C8	121.0 (5)	N5—C22—C23	123.8 (6)
C3—C4—C8	119.4 (5)	C24—C23—C22	115.7 (5)
C4—C5—C6	121.5 (5)	N6—C24—C23	124.4 (6)
C4—C5—C20	119.8 (5)	Cl2—C25—Cl1	113.9 (7)
C6—C5—C20	118.7 (5)	Cl2—C25—Cl3	109.9 (6)
C1—C6—C5	118.1 (5)	Cl1—C25—Cl3	107.5 (5)
C1—C6—C9	121.8 (5)
C6—C1—C2—C3	3.8 (8)	C10—S1—C11—N2	173.4 (4)
C10—C1—C2—C3	−174.3 (5)	C11—N1—C12—C13	−0.8 (8)
C6—C1—C2—C7	−175.5 (5)	N1—C12—C13—C14	0.8 (10)
C10—C1—C2—C7	6.3 (8)	C12—C13—C14—N2	−1.6 (11)
C1—C2—C3—C4	−1.9 (8)	C11—N2—C14—C13	2.2 (10)
C7—C2—C3—C4	177.4 (5)	C2—C3—C15—S2	96.7 (5)
C1—C2—C3—C15	176.6 (5)	C4—C3—C15—S2	−84.8 (5)
C7—C2—C3—C15	−4.1 (8)	C16—S2—C15—C3	165.7 (4)
C2—C3—C4—C5	0.7 (8)	C17—N3—C16—N4	3.2 (9)
C15—C3—C4—C5	−177.8 (5)	C17—N3—C16—S2	−178.2 (5)
C2—C3—C4—C8	−176.7 (5)	C19—N4—C16—N3	−2.6 (9)
C15—C3—C4—C8	4.8 (7)	C19—N4—C16—S2	178.7 (5)
C3—C4—C5—C6	−1.2 (8)	C15—S2—C16—N3	12.3 (6)
C8—C4—C5—C6	176.1 (5)	C15—S2—C16—N4	−169.0 (5)
C3—C4—C5—C20	179.3 (5)	C16—N3—C17—C18	−1.2 (10)
C8—C4—C5—C20	−3.3 (7)	N3—C17—C18—C19	−1.1 (10)
C2—C1—C6—C5	−4.3 (8)	C16—N4—C19—C18	0.0 (10)
C10—C1—C6—C5	173.8 (4)	C17—C18—C19—N4	1.7 (11)
C2—C1—C6—C9	174.4 (5)	C4—C5—C20—S3	91.7 (5)
C10—C1—C6—C9	−7.4 (7)	C6—C5—C20—S3	−87.8 (5)
C4—C5—C6—C1	3.0 (7)	C21—S3—C20—C5	−166.3 (4)
C20—C5—C6—C1	−177.6 (4)	C22—N5—C21—N6	−3.0 (8)
C4—C5—C6—C9	−175.8 (5)	C22—N5—C21—S3	177.2 (4)
C20—C5—C6—C9	3.7 (7)	C24—N6—C21—N5	1.7 (8)
C6—C1—C10—S1	92.7 (5)	C24—N6—C21—S3	−178.5 (4)
C2—C1—C10—S1	−89.0 (5)	C20—S3—C21—N5	0.1 (5)
C11—S1—C10—C1	−174.9 (4)	C20—S3—C21—N6	−179.8 (4)
C12—N1—C11—N2	1.6 (9)	C21—N5—C22—C23	2.0 (8)
C12—N1—C11—S1	−177.1 (4)	N5—C22—C23—C24	0.0 (8)
C14—N2—C11—N1	−2.3 (9)	C21—N6—C24—C23	0.8 (8)
C14—N2—C11—S1	176.5 (5)	C22—C23—C24—N6	−1.5 (9)
C10—S1—C11—N1	−7.6 (5)