Download citation
Download citation
link to html
The title compound, C21H27N3S6, was synthesized by the reaction of 2,4,6-trimethyl-1,3,5-tris­(bromo­meth­yl)benzene and thia­zoline-2-thione. In the mol­ecule, two thia­zoline rings are located on one side of the central benzene plane, while the third thia­zoline ring is located on the other side of the central benzene plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603697X/at2103sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603697X/at2103Isup2.hkl
Contains datablock I

CCDC reference: 623966

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.131
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.617 1.000 Tmin(prime) and Tmax expected: 0.900 0.944 RR(prime) = 0.647 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.65
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S4 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S6 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.944 Tmax scaled 0.944 Tmin scaled 0.583
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.

2,4,6-trimethyl-1,3,5-tris(2-thiazolin-2-ylsulfanylmethyl)benzene top
Crystal data top
C21H27N3S6F(000) = 2160
Mr = 513.82Dx = 1.390 Mg m3
Monoclinic, C2/cMelting point: 421 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 19.834 (4) ÅCell parameters from 2707 reflections
b = 14.899 (3) Åθ = 2.5–24.3°
c = 16.797 (3) ŵ = 0.57 mm1
β = 98.381 (3)°T = 294 K
V = 4910.5 (15) Å3Block, colourless
Z = 80.18 × 0.14 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4341 independent reflections
Radiation source: fine-focus sealed tube2688 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2323
Tmin = 0.617, Tmax = 1.000k = 1117
12381 measured reflectionsl = 1919
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0638P)2 + 0.8708P]
where P = (Fo2 + 2Fc2)/3
4341 reflections(Δ/σ)max = 0.004
274 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

Experimental. IR (KBr, ν cm-1): 2928, 2848, 1558, 1434, 1378, 1304, 1220, 1188, 1056, 968, 918, 792, 692; 1H NMR (CDCl3): δ 2.43 (s, 9H), 3.44 (t, 6H), 4.28 (t, 6H), 4.46 (t, 6H). Analysis calculated for C21H27N3S6: C 49.12, H 5.26, N 8.19%; found: C 49.14, H 5.31, N 8.23%.

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
S10.69382 (7)0.06598 (6)0.55769 (6)0.0630 (3)
S20.70854 (6)0.05293 (6)0.41750 (5)0.0545 (3)
S30.58346 (5)0.41844 (6)0.19247 (6)0.0525 (3)
S40.47992 (5)0.56111 (6)0.14165 (6)0.0556 (3)
S50.88594 (6)0.34316 (7)0.19392 (7)0.0630 (3)
S60.99320 (6)0.44317 (7)0.12417 (7)0.0649 (3)
N10.73186 (15)0.10180 (19)0.57249 (16)0.0458 (8)
N20.47244 (14)0.3971 (2)0.08286 (18)0.0466 (8)
N30.94744 (16)0.2847 (2)0.0716 (2)0.0549 (9)
C10.78181 (16)0.2022 (2)0.28660 (19)0.0337 (8)
C20.72376 (17)0.1998 (2)0.32444 (18)0.0332 (8)
C30.66077 (16)0.2285 (2)0.28342 (19)0.0340 (8)
C40.65764 (16)0.2655 (2)0.20628 (18)0.0308 (8)
C50.71609 (16)0.27203 (19)0.16963 (18)0.0296 (7)
C60.77811 (16)0.23680 (19)0.20862 (19)0.0310 (8)
C70.7290 (2)0.1711 (2)0.41155 (19)0.0456 (10)
H7A0.69770.20620.43830.055*
H7B0.77490.18180.43880.055*
C80.71419 (17)0.0407 (2)0.5216 (2)0.0365 (8)
C90.7002 (3)0.0212 (3)0.6572 (2)0.0735 (14)
H9A0.65530.01450.67290.088*
H9B0.72700.06060.69540.088*
C100.7342 (2)0.0682 (3)0.6549 (2)0.0617 (12)
H10A0.71200.11110.68590.074*
H10B0.78140.06310.67970.074*
C110.5968 (2)0.2195 (3)0.3222 (3)0.0675 (12)
H11A0.60770.19030.37340.101*
H11B0.56380.18440.28810.101*
H11C0.57850.27800.32960.101*
C120.59059 (17)0.3011 (2)0.1631 (2)0.0448 (9)
H12A0.55290.26660.17810.054*
H12B0.58950.29660.10530.054*
C130.50721 (16)0.4488 (2)0.1322 (2)0.0367 (8)
C140.41131 (19)0.4432 (3)0.0434 (2)0.0609 (12)
H14A0.37140.41670.06120.073*
H14B0.40750.43430.01430.073*
C150.4124 (2)0.5419 (3)0.0610 (2)0.0645 (13)
H15A0.36920.56060.07620.077*
H15B0.42010.57560.01380.077*
C160.7126 (2)0.3174 (2)0.08881 (19)0.0509 (10)
H16A0.69150.27780.04740.076*
H16B0.75790.33190.07900.076*
H16C0.68620.37150.08860.076*
C170.83996 (17)0.2393 (2)0.1661 (2)0.0435 (9)
H17A0.82620.23710.10830.052*
H17B0.86900.18810.18180.052*
C180.94160 (18)0.3453 (2)0.1237 (2)0.0453 (9)
C191.0421 (2)0.3851 (3)0.0573 (3)0.0715 (13)
H19A1.05530.42580.01730.086*
H19B1.08290.35880.08720.086*
C200.9956 (2)0.3138 (3)0.0185 (3)0.0741 (14)
H20A0.97060.33670.03130.089*
H20B1.02240.26280.00540.089*
C210.84907 (19)0.1667 (3)0.3297 (3)0.0660 (12)
H21A0.85920.19470.38150.099*
H21B0.88470.17990.29850.099*
H21C0.84590.10290.33640.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1153 (10)0.0300 (6)0.0468 (6)0.0103 (5)0.0226 (6)0.0024 (4)
S20.0998 (9)0.0298 (5)0.0331 (5)0.0092 (5)0.0075 (5)0.0012 (4)
S30.0438 (6)0.0412 (6)0.0651 (7)0.0154 (4)0.0169 (5)0.0047 (5)
S40.0505 (6)0.0423 (6)0.0670 (7)0.0149 (5)0.0148 (5)0.0022 (5)
S50.0649 (7)0.0534 (7)0.0783 (8)0.0199 (5)0.0363 (6)0.0188 (6)
S60.0622 (7)0.0555 (7)0.0795 (8)0.0203 (5)0.0185 (6)0.0015 (6)
N10.069 (2)0.0341 (18)0.0348 (17)0.0069 (15)0.0077 (15)0.0038 (14)
N20.0373 (18)0.0464 (19)0.0529 (19)0.0081 (14)0.0046 (15)0.0054 (15)
N30.050 (2)0.054 (2)0.065 (2)0.0100 (16)0.0232 (17)0.0072 (18)
C10.033 (2)0.0266 (19)0.0388 (19)0.0003 (15)0.0025 (16)0.0002 (15)
C20.049 (2)0.0208 (18)0.0292 (18)0.0027 (15)0.0026 (16)0.0019 (13)
C30.040 (2)0.0243 (18)0.0405 (19)0.0042 (15)0.0158 (16)0.0006 (15)
C40.034 (2)0.0221 (18)0.0354 (19)0.0041 (14)0.0025 (15)0.0003 (14)
C50.037 (2)0.0212 (17)0.0304 (17)0.0014 (14)0.0038 (15)0.0004 (13)
C60.0334 (19)0.0237 (18)0.0377 (19)0.0007 (14)0.0110 (15)0.0038 (14)
C70.069 (3)0.031 (2)0.035 (2)0.0005 (17)0.0034 (18)0.0026 (15)
C80.043 (2)0.030 (2)0.037 (2)0.0047 (16)0.0098 (16)0.0075 (16)
C90.133 (4)0.048 (3)0.045 (3)0.004 (3)0.030 (3)0.008 (2)
C100.099 (3)0.049 (3)0.038 (2)0.014 (2)0.013 (2)0.0009 (18)
C110.057 (3)0.076 (3)0.076 (3)0.016 (2)0.033 (2)0.022 (2)
C120.036 (2)0.037 (2)0.058 (2)0.0057 (16)0.0063 (17)0.0021 (17)
C130.0316 (19)0.039 (2)0.039 (2)0.0063 (16)0.0045 (16)0.0047 (16)
C140.042 (2)0.071 (3)0.063 (3)0.011 (2)0.017 (2)0.014 (2)
C150.052 (3)0.073 (3)0.062 (3)0.024 (2)0.016 (2)0.004 (2)
C160.071 (3)0.047 (2)0.034 (2)0.003 (2)0.0090 (19)0.0112 (17)
C170.041 (2)0.036 (2)0.056 (2)0.0016 (16)0.0162 (18)0.0057 (17)
C180.037 (2)0.042 (2)0.057 (2)0.0011 (17)0.0063 (18)0.0077 (19)
C190.055 (3)0.073 (3)0.091 (3)0.005 (2)0.028 (3)0.012 (3)
C200.068 (3)0.084 (4)0.078 (3)0.014 (3)0.035 (3)0.020 (3)
C210.051 (3)0.060 (3)0.081 (3)0.009 (2)0.012 (2)0.024 (2)
Geometric parameters (Å, º) top
S1—C81.769 (3)C7—H7A0.9700
S1—C91.787 (4)C7—H7B0.9700
S2—C81.745 (3)C9—C101.497 (5)
S2—C71.812 (3)C9—H9A0.9700
S3—C131.753 (3)C9—H9B0.9700
S3—C121.827 (3)C10—H10A0.9700
S4—C131.772 (3)C10—H10B0.9700
S4—C151.784 (4)C11—H11A0.9600
S5—C181.730 (4)C11—H11B0.9600
S5—C171.822 (3)C11—H11C0.9600
S6—C181.780 (4)C12—H12A0.9700
S6—C191.808 (4)C12—H12B0.9700
N1—C81.263 (4)C14—C151.499 (5)
N1—C101.465 (4)C14—H14A0.9700
N2—C131.261 (4)C14—H14B0.9700
N2—C141.465 (4)C15—H15A0.9700
N3—C181.275 (4)C15—H15B0.9700
N3—C201.465 (5)C16—H16A0.9600
C1—C21.394 (4)C16—H16B0.9600
C1—C61.399 (4)C16—H16C0.9600
C1—C211.518 (4)C17—H17A0.9700
C2—C31.402 (4)C17—H17B0.9700
C2—C71.514 (4)C19—C201.493 (5)
C3—C41.401 (4)C19—H19A0.9700
C3—C111.513 (5)C19—H19B0.9700
C4—C51.393 (4)C20—H20A0.9700
C4—C121.515 (4)C20—H20B0.9700
C5—C61.408 (4)C21—H21A0.9600
C5—C161.509 (4)C21—H21B0.9600
C6—C171.507 (4)C21—H21C0.9600
C8—S1—C989.81 (17)C4—C12—S3107.7 (2)
C8—S2—C7100.04 (15)C4—C12—H12A110.2
C13—S3—C12100.70 (15)S3—C12—H12A110.2
C13—S4—C1589.16 (17)C4—C12—H12B110.2
C18—S5—C17100.73 (17)S3—C12—H12B110.2
C18—S6—C1988.00 (19)H12A—C12—H12B108.5
C8—N1—C10111.1 (3)N2—C13—S3124.4 (3)
C13—N2—C14110.4 (3)N2—C13—S4119.4 (3)
C18—N3—C20109.9 (3)S3—C13—S4116.18 (19)
C2—C1—C6120.1 (3)N2—C14—C15112.5 (3)
C2—C1—C21120.0 (3)N2—C14—H14A109.1
C6—C1—C21119.8 (3)C15—C14—H14A109.1
C1—C2—C3120.3 (3)N2—C14—H14B109.1
C1—C2—C7120.2 (3)C15—C14—H14B109.1
C3—C2—C7119.5 (3)H14A—C14—H14B107.8
C4—C3—C2119.4 (3)C14—C15—S4107.1 (3)
C4—C3—C11120.4 (3)C14—C15—H15A110.3
C2—C3—C11120.3 (3)S4—C15—H15A110.3
C5—C4—C3120.6 (3)C14—C15—H15B110.3
C5—C4—C12119.6 (3)S4—C15—H15B110.3
C3—C4—C12119.9 (3)H15A—C15—H15B108.5
C4—C5—C6119.7 (3)C5—C16—H16A109.5
C4—C5—C16119.8 (3)C5—C16—H16B109.5
C6—C5—C16120.5 (3)H16A—C16—H16B109.5
C1—C6—C5119.7 (3)C5—C16—H16C109.5
C1—C6—C17121.2 (3)H16A—C16—H16C109.5
C5—C6—C17119.1 (3)H16B—C16—H16C109.5
C2—C7—S2110.1 (2)C6—C17—S5108.1 (2)
C2—C7—H7A109.6C6—C17—H17A110.1
S2—C7—H7A109.6S5—C17—H17A110.1
C2—C7—H7B109.6C6—C17—H17B110.1
S2—C7—H7B109.6S5—C17—H17B110.1
H7A—C7—H7B108.2H17A—C17—H17B108.4
N1—C8—S2125.0 (3)N3—C18—S5125.9 (3)
N1—C8—S1118.1 (3)N3—C18—S6118.3 (3)
S2—C8—S1116.9 (2)S5—C18—S6115.8 (2)
C10—C9—S1106.2 (3)C20—C19—S6105.0 (3)
C10—C9—H9A110.5C20—C19—H19A110.7
S1—C9—H9A110.5S6—C19—H19A110.7
C10—C9—H9B110.5C20—C19—H19B110.7
S1—C9—H9B110.5S6—C19—H19B110.7
H9A—C9—H9B108.7H19A—C19—H19B108.8
N1—C10—C9112.1 (3)N3—C20—C19111.1 (3)
N1—C10—H10A109.2N3—C20—H20A109.4
C9—C10—H10A109.2C19—C20—H20A109.4
N1—C10—H10B109.2N3—C20—H20B109.4
C9—C10—H10B109.2C19—C20—H20B109.4
H10A—C10—H10B107.9H20A—C20—H20B108.0
C3—C11—H11A109.5C1—C21—H21A109.5
C3—C11—H11B109.5C1—C21—H21B109.5
H11A—C11—H11B109.5H21A—C21—H21B109.5
C3—C11—H11C109.5C1—C21—H21C109.5
H11A—C11—H11C109.5H21A—C21—H21C109.5
H11B—C11—H11C109.5H21B—C21—H21C109.5
C6—C1—C2—C32.7 (5)C7—S2—C8—S1177.0 (2)
C21—C1—C2—C3176.8 (3)C9—S1—C8—N17.2 (3)
C6—C1—C2—C7174.0 (3)C9—S1—C8—S2173.1 (2)
C21—C1—C2—C76.5 (5)C8—S1—C9—C1013.4 (3)
C1—C2—C3—C44.6 (5)C8—N1—C10—C913.3 (5)
C7—C2—C3—C4172.1 (3)S1—C9—C10—N117.6 (5)
C1—C2—C3—C11175.5 (3)C5—C4—C12—S390.3 (3)
C7—C2—C3—C117.8 (5)C3—C4—C12—S388.0 (3)
C2—C3—C4—C51.5 (4)C13—S3—C12—C4176.1 (2)
C11—C3—C4—C5178.5 (3)C14—N2—C13—S3179.1 (3)
C2—C3—C4—C12176.8 (3)C14—N2—C13—S42.2 (4)
C11—C3—C4—C123.2 (5)C12—S3—C13—N21.3 (4)
C3—C4—C5—C63.4 (4)C12—S3—C13—S4180.0 (2)
C12—C4—C5—C6178.3 (3)C15—S4—C13—N24.5 (3)
C3—C4—C5—C16176.1 (3)C15—S4—C13—S3174.2 (2)
C12—C4—C5—C162.2 (4)C13—N2—C14—C159.7 (5)
C2—C1—C6—C52.2 (5)N2—C14—C15—S412.5 (4)
C21—C1—C6—C5178.2 (3)C13—S4—C15—C149.2 (3)
C2—C1—C6—C17179.4 (3)C1—C6—C17—S586.9 (3)
C21—C1—C6—C170.1 (5)C5—C6—C17—S591.5 (3)
C4—C5—C6—C15.3 (4)C18—S5—C17—C6167.1 (2)
C16—C5—C6—C1174.3 (3)C20—N3—C18—S5175.2 (3)
C4—C5—C6—C17176.3 (3)C20—N3—C18—S63.2 (4)
C16—C5—C6—C174.1 (4)C17—S5—C18—N33.3 (4)
C1—C2—C7—S295.9 (3)C17—S5—C18—S6175.2 (2)
C3—C2—C7—S287.4 (3)C19—S6—C18—N312.3 (3)
C8—S2—C7—C2177.1 (3)C19—S6—C18—S5169.1 (2)
C10—N1—C8—S2177.4 (3)C18—S6—C19—C2022.2 (3)
C10—N1—C8—S12.3 (4)C18—N3—C20—C1921.7 (5)
C7—S2—C8—N13.3 (4)S6—C19—C20—N329.2 (4)
 

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