Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016829/ww6097sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016829/ww6097Isup2.hkl |
CCDC reference: 222844
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.059
- wR factor = 0.114
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .. 49 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) . 2.63 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .. S1 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .. S3 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .. S4 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .. S5 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .. S6' PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .. S6 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .. C16 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .. C18 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .. C21' PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .. C21 PLAT301_ALERT_3_C Main Residue Disorder ....................... 15.00 Perc. PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue ? PLAT322_ALERT_2_C Check Hybridisation of S4 in Main Residue ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang.. 6 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety .... C14 PLAT413_ALERT_2_C Short Inter XH3 .. XHn : H10B .. H24B = 2.11 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF .... 7.00 Deg. C21 -S5 -C21' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 19 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 15 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
2,4,6-Trimethyl-1,3,5-tris(bromomethyl)benzene was prepared according to a reported method (van der Made & van der Made, 1993). The title compound was synthesized according to a reported procedure (Zhang et al., 2003) by the reaction of 2,4,6-trimethyl-1,3,5-tris(bromomethyl)benzene and potassium 4-methylthiazolylthiolate in EtOH at 323–333 K; yield 87.4%; m.p. 388–389 K; IR (KBr) 3111 (w), 2960 (w), 2916 (w), 1527 (ms), 1414 (s), 1414 (s), 1372 (ms), 1289 (s), 1032 (versus), 723 (w), 706 (ms) cm−1; 1H NMR (CDCl3) δ 6.81 (3H, s), 4.49 (6H, s), 2.49 (9H, s), 2.45 (9H, s) p.p.m.; elemental analysis calculated for C24H27N3S6 C 52.40, H 4.90, N 7.63%; found C 52.40, H 4.88, N 7.47%. The single crystals of (I), suitable for X-ray analysis, were obtained by slow diffusion of acetone into the chloroform solution of (I).
In the disorderd thiazolyl ring, the bonds S6—C21, S6–22, S6'-C21', S6'-C22' were restrained to 1.71 (1) Å and the angles C21—S6—C22, C21'-S6'-C22' to 89 (1)°; other C—C and C—N bond parameters were restrained to appropriate values. The primed atoms have occupancy 0.53 (3) and the unprimed 0.47 (3).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997); 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.
Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level. |
C24H27N3S6 | F(000) = 1152 |
Mr = 549.91 | Dx = 1.343 Mg m−3 |
Monoclinic, P21/n | Melting point = 388–389 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.216 (4) Å | Cell parameters from 992 reflections |
b = 17.801 (5) Å | θ = 2.5–21.4° |
c = 12.528 (4) Å | µ = 0.52 mm−1 |
β = 93.420 (6)° | T = 293 K |
V = 2719.4 (15) Å3 | Prism, colorless |
Z = 4 | 0.25 × 0.20 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 4780 independent reflections |
Radiation source: fine-focus sealed tube | 2335 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→13 |
Tmin = 0.880, Tmax = 0.927 | k = −17→21 |
12608 measured reflections | l = −10→14 |
Refinement on F2 | 252 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.0343P)2 + 0.7831P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max = 0.003 |
S = 1.00 | Δρmax = 0.25 e Å−3 |
4772 reflections | Δρmin = −0.19 e Å−3 |
360 parameters |
C24H27N3S6 | V = 2719.4 (15) Å3 |
Mr = 549.91 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.216 (4) Å | µ = 0.52 mm−1 |
b = 17.801 (5) Å | T = 293 K |
c = 12.528 (4) Å | 0.25 × 0.20 × 0.15 mm |
β = 93.420 (6)° |
Bruker SMART CCD area-detector diffractometer | 4780 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2335 reflections with I > 2σ(I) |
Tmin = 0.880, Tmax = 0.927 | Rint = 0.069 |
12608 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 252 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.25 e Å−3 |
4772 reflections | Δρmin = −0.19 e Å−3 |
360 parameters |
Experimental. The corresponding bond distances and angles of the disorderd thiazolyl ring S6'-C21'-C22'-C23'-N3'-C24' were restrained to that of S6—C21—C22—C23—N3—C24. i.e. the bond lengths S6—C21, S6–22, S6'-C21', S6'-C22' are restrained to 1.71 (1) Å, and the angles C21—S6—C22, C21'-S6'-C22' are restrained to 89 (1)°, other C—C and C—N bond parameters are restrained to appropriate values. |
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 > 2σ(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.58944 (9) | 0.04420 (6) | 0.72001 (10) | 0.0737 (4) | |
S2 | 0.38138 (9) | 0.11800 (7) | 0.78092 (10) | 0.0697 (4) | |
S3 | 0.89432 (12) | −0.22489 (6) | 0.57718 (9) | 0.0802 (4) | |
S4 | 0.87887 (13) | −0.38177 (7) | 0.49189 (14) | 0.1094 (5) | |
S5 | 1.07953 (10) | 0.01463 (6) | 0.89455 (9) | 0.0730 (4) | |
S6 | 1.2236 (12) | 0.0415 (6) | 1.0833 (12) | 0.092 (3) | 0.47 (3) |
C21 | 1.167 (2) | 0.0760 (10) | 0.9661 (14) | 0.047 (5) | 0.47 (3) |
C22 | 1.2816 (17) | 0.1276 (9) | 1.1064 (14) | 0.084 (6) | 0.47 (3) |
H22 | 1.3261 | 0.1399 | 1.1667 | 0.101* | 0.47 (3) |
C23 | 1.2551 (16) | 0.1748 (8) | 1.0272 (14) | 0.063 (6) | 0.47 (3) |
N3 | 1.188 (3) | 0.1450 (11) | 0.9446 (14) | 0.051 (6) | 0.47 (3) |
C24 | 1.290 (2) | 0.2560 (9) | 1.018 (2) | 0.090 (9) | 0.47 (3) |
H24A | 1.3399 | 0.2687 | 1.0774 | 0.135* | 0.47 (3) |
H24B | 1.2269 | 0.2880 | 1.0178 | 0.135* | 0.47 (3) |
H24C | 1.3261 | 0.2629 | 0.9525 | 0.135* | 0.47 (3) |
S6' | 1.1851 (12) | 0.0650 (9) | 1.1088 (7) | 0.089 (3) | 0.53 (3) |
C21' | 1.154 (2) | 0.0802 (9) | 0.9754 (12) | 0.052 (5) | 0.53 (3) |
C22' | 1.2543 (15) | 0.1484 (10) | 1.1150 (12) | 0.076 (5) | 0.53 (3) |
H22A | 1.2900 | 0.1682 | 1.1763 | 0.092* | 0.53 (3) |
C23' | 1.2495 (13) | 0.1812 (6) | 1.0192 (13) | 0.053 (5) | 0.53 (3) |
N3' | 1.192 (2) | 0.1422 (9) | 0.9379 (13) | 0.050 (5) | 0.53 (3) |
C24' | 1.3007 (19) | 0.2557 (7) | 0.9911 (18) | 0.069 (5) | 0.53 (3) |
H24D | 1.3365 | 0.2773 | 1.0541 | 0.103* | 0.53 (3) |
H24E | 1.2445 | 0.2892 | 0.9630 | 0.103* | 0.53 (3) |
H24F | 1.3534 | 0.2478 | 0.9384 | 0.103* | 0.53 (3) |
N1 | 0.5027 (3) | 0.17344 (19) | 0.6409 (3) | 0.0618 (10) | |
N2 | 0.9259 (3) | −0.27008 (19) | 0.3751 (3) | 0.0674 (10) | |
C1 | 0.7899 (3) | 0.0318 (2) | 0.6336 (3) | 0.0470 (10) | |
C2 | 0.8783 (3) | 0.0609 (2) | 0.6969 (3) | 0.0469 (10) | |
C3 | 0.9793 (3) | 0.0248 (2) | 0.6980 (3) | 0.0442 (9) | |
C4 | 0.9924 (3) | −0.0414 (2) | 0.6398 (3) | 0.0468 (10) | |
C5 | 0.9029 (3) | −0.0700 (2) | 0.5779 (3) | 0.0494 (10) | |
C6 | 0.8012 (3) | −0.0347 (2) | 0.5771 (3) | 0.0513 (10) | |
C7 | 0.7034 (3) | −0.0687 (2) | 0.5134 (4) | 0.0808 (14) | |
H7A | 0.6371 | −0.0552 | 0.5461 | 0.121* | |
H7B | 0.7105 | −0.1224 | 0.5126 | 0.121* | |
H7C | 0.7010 | −0.0500 | 0.4415 | 0.121* | |
C8 | 1.1015 (3) | −0.0820 (2) | 0.6446 (3) | 0.0711 (13) | |
H8A | 1.0892 | −0.1352 | 0.6403 | 0.107* | |
H8B | 1.1417 | −0.0702 | 0.7106 | 0.107* | |
H8C | 1.1429 | −0.0663 | 0.5857 | 0.107* | |
C9 | 0.8637 (3) | 0.1293 (2) | 0.7669 (3) | 0.0690 (13) | |
H9A | 0.9000 | 0.1716 | 0.7373 | 0.103* | |
H9B | 0.8949 | 0.1195 | 0.8377 | 0.103* | |
H9C | 0.7870 | 0.1401 | 0.7701 | 0.103* | |
C10 | 0.6835 (3) | 0.0744 (2) | 0.6222 (3) | 0.0615 (12) | |
H10A | 0.6500 | 0.0666 | 0.5509 | 0.074* | |
H10B | 0.6980 | 0.1277 | 0.6311 | 0.074* | |
C11 | 0.4942 (3) | 0.1174 (2) | 0.7055 (3) | 0.0546 (11) | |
C12 | 0.3422 (4) | 0.2001 (2) | 0.7194 (4) | 0.0697 (13) | |
H12 | 0.2786 | 0.2264 | 0.7326 | 0.084* | |
C13 | 0.4142 (4) | 0.2216 (2) | 0.6503 (4) | 0.0656 (12) | |
C14 | 0.4099 (4) | 0.2905 (3) | 0.5811 (4) | 0.1088 (19) | |
H14A | 0.4074 | 0.2759 | 0.5072 | 0.163* | |
H14B | 0.4741 | 0.3206 | 0.5973 | 0.163* | |
H14C | 0.3456 | 0.3192 | 0.5945 | 0.163* | |
C15 | 0.9189 (3) | −0.13771 (19) | 0.5068 (3) | 0.0620 (12) | |
H15A | 0.9932 | −0.1377 | 0.4834 | 0.074* | |
H15B | 0.8689 | −0.1344 | 0.4438 | 0.074* | |
C16 | 0.9039 (4) | −0.2878 (2) | 0.4713 (4) | 0.0675 (13) | |
C17 | 0.8996 (5) | −0.3966 (3) | 0.3602 (5) | 0.110 (2) | |
H17 | 0.8946 | −0.4434 | 0.3273 | 0.132* | |
C18 | 0.9241 (4) | −0.3330 (3) | 0.3096 (5) | 0.0823 (15) | |
C19 | 0.9500 (5) | −0.3251 (3) | 0.1959 (4) | 0.117 (2) | |
H19A | 0.9079 | −0.2846 | 0.1638 | 0.175* | |
H19B | 0.9322 | −0.3709 | 0.1585 | 0.175* | |
H19C | 1.0268 | −0.3146 | 0.1919 | 0.175* | |
C20 | 1.0758 (3) | 0.0581 (2) | 0.7634 (3) | 0.0566 (11) | |
H20A | 1.0671 | 0.1120 | 0.7697 | 0.068* | |
H20B | 1.1435 | 0.0481 | 0.7293 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0582 (8) | 0.0782 (8) | 0.0866 (9) | 0.0139 (6) | 0.0210 (7) | 0.0264 (7) |
S2 | 0.0516 (7) | 0.0878 (9) | 0.0703 (8) | 0.0050 (6) | 0.0096 (6) | −0.0024 (7) |
S3 | 0.1171 (11) | 0.0646 (8) | 0.0590 (8) | −0.0089 (7) | 0.0061 (7) | −0.0015 (6) |
S4 | 0.1386 (14) | 0.0576 (9) | 0.1305 (15) | −0.0007 (8) | −0.0041 (11) | 0.0015 (8) |
S5 | 0.0888 (9) | 0.0709 (8) | 0.0571 (8) | −0.0337 (7) | −0.0151 (7) | 0.0128 (6) |
S6 | 0.097 (5) | 0.092 (4) | 0.080 (4) | −0.016 (3) | −0.049 (3) | 0.023 (3) |
C21 | 0.041 (10) | 0.061 (11) | 0.040 (9) | −0.008 (9) | 0.009 (8) | −0.002 (9) |
C22 | 0.075 (10) | 0.106 (11) | 0.067 (9) | −0.019 (9) | −0.034 (8) | 0.016 (8) |
C23 | 0.061 (11) | 0.071 (11) | 0.056 (11) | −0.010 (10) | −0.012 (10) | −0.008 (10) |
N3 | 0.056 (11) | 0.061 (11) | 0.034 (9) | 0.007 (10) | −0.007 (9) | −0.010 (9) |
C24 | 0.120 (17) | 0.099 (14) | 0.049 (12) | 0.014 (11) | −0.009 (10) | 0.010 (10) |
S6' | 0.098 (5) | 0.108 (5) | 0.058 (3) | −0.050 (4) | −0.026 (3) | 0.032 (3) |
C21' | 0.034 (8) | 0.065 (10) | 0.055 (10) | −0.011 (7) | −0.009 (8) | 0.010 (8) |
C22' | 0.071 (9) | 0.088 (9) | 0.066 (8) | −0.039 (8) | −0.029 (7) | 0.008 (7) |
C23' | 0.045 (9) | 0.061 (9) | 0.052 (9) | −0.003 (8) | 0.009 (8) | −0.005 (8) |
N3' | 0.056 (10) | 0.043 (9) | 0.053 (10) | −0.013 (8) | 0.007 (8) | −0.002 (8) |
C24' | 0.097 (11) | 0.057 (8) | 0.054 (11) | −0.037 (8) | 0.014 (8) | −0.036 (6) |
N1 | 0.055 (2) | 0.062 (2) | 0.068 (3) | 0.006 (2) | 0.0016 (19) | 0.003 (2) |
N2 | 0.076 (3) | 0.061 (2) | 0.063 (3) | 0.0150 (19) | −0.014 (2) | −0.015 (2) |
C1 | 0.043 (3) | 0.057 (3) | 0.042 (2) | −0.002 (2) | 0.009 (2) | 0.008 (2) |
C2 | 0.059 (3) | 0.046 (2) | 0.037 (2) | −0.006 (2) | 0.009 (2) | −0.0013 (19) |
C3 | 0.045 (3) | 0.051 (2) | 0.038 (2) | −0.008 (2) | 0.0060 (19) | 0.0013 (19) |
C4 | 0.048 (3) | 0.052 (3) | 0.042 (2) | 0.000 (2) | 0.010 (2) | 0.002 (2) |
C5 | 0.060 (3) | 0.051 (2) | 0.038 (2) | −0.007 (2) | 0.009 (2) | −0.002 (2) |
C6 | 0.048 (3) | 0.064 (3) | 0.042 (3) | −0.011 (2) | 0.001 (2) | 0.000 (2) |
C7 | 0.067 (3) | 0.100 (4) | 0.072 (3) | −0.013 (3) | −0.016 (3) | −0.020 (3) |
C8 | 0.064 (3) | 0.074 (3) | 0.076 (3) | 0.012 (2) | 0.007 (3) | −0.005 (2) |
C9 | 0.080 (3) | 0.062 (3) | 0.066 (3) | 0.005 (2) | 0.008 (3) | −0.008 (2) |
C10 | 0.050 (3) | 0.073 (3) | 0.062 (3) | 0.005 (2) | 0.010 (2) | 0.012 (2) |
C11 | 0.045 (3) | 0.065 (3) | 0.053 (3) | 0.001 (2) | 0.001 (2) | −0.002 (2) |
C12 | 0.055 (3) | 0.081 (3) | 0.072 (3) | 0.012 (3) | −0.004 (3) | −0.021 (3) |
C13 | 0.067 (4) | 0.058 (3) | 0.070 (3) | 0.010 (3) | −0.010 (3) | −0.011 (3) |
C14 | 0.121 (5) | 0.074 (4) | 0.132 (5) | 0.027 (3) | 0.009 (4) | 0.016 (3) |
C15 | 0.077 (3) | 0.062 (3) | 0.047 (3) | 0.000 (2) | 0.002 (2) | −0.005 (2) |
C16 | 0.073 (3) | 0.055 (3) | 0.072 (3) | 0.002 (2) | −0.012 (3) | −0.007 (3) |
C17 | 0.134 (5) | 0.074 (4) | 0.120 (5) | 0.013 (3) | −0.018 (4) | −0.035 (4) |
C18 | 0.081 (4) | 0.075 (4) | 0.087 (4) | 0.018 (3) | −0.026 (3) | −0.024 (3) |
C19 | 0.138 (5) | 0.126 (5) | 0.083 (5) | 0.043 (4) | −0.021 (4) | −0.040 (4) |
C20 | 0.061 (3) | 0.058 (3) | 0.050 (3) | −0.012 (2) | 0.000 (2) | 0.005 (2) |
S1—C11 | 1.748 (4) | C1—C10 | 1.503 (5) |
S1—C10 | 1.811 (4) | C2—C3 | 1.392 (5) |
S2—C12 | 1.708 (5) | C2—C9 | 1.518 (5) |
S2—C11 | 1.717 (4) | C3—C4 | 1.398 (5) |
S3—C16 | 1.745 (5) | C3—C20 | 1.516 (5) |
S3—C15 | 1.819 (4) | C4—C5 | 1.398 (5) |
S4—C17 | 1.705 (6) | C4—C8 | 1.515 (5) |
S4—C16 | 1.724 (4) | C5—C6 | 1.392 (5) |
S5—C21 | 1.736 (10) | C5—C15 | 1.518 (5) |
S5—C21' | 1.763 (9) | C6—C7 | 1.521 (5) |
S5—C20 | 1.814 (4) | C7—H7A | 0.9600 |
S6—C21 | 1.702 (12) | C7—H7B | 0.9600 |
S6—C22 | 1.706 (11) | C7—H7C | 0.9600 |
C21—N3 | 1.286 (10) | C8—H8A | 0.9600 |
C22—C23 | 1.325 (12) | C8—H8B | 0.9600 |
C22—H22 | 0.9300 | C8—H8C | 0.9600 |
C23—N3 | 1.389 (10) | C9—H9A | 0.9600 |
C23—C24 | 1.516 (8) | C9—H9B | 0.9600 |
C24—H24A | 0.9600 | C9—H9C | 0.9600 |
C24—H24B | 0.9600 | C10—H10A | 0.9700 |
C24—H24C | 0.9600 | C10—H10B | 0.9700 |
S6'—C22' | 1.707 (9) | C12—C13 | 1.326 (6) |
S6'—C21' | 1.713 (10) | C12—H12 | 0.9300 |
C21'—N3' | 1.296 (9) | C13—C14 | 1.502 (6) |
C22'—C23' | 1.332 (10) | C14—H14A | 0.9600 |
C22'—H22A | 0.9300 | C14—H14B | 0.9600 |
C23'—N3' | 1.388 (9) | C14—H14C | 0.9600 |
C23'—C24' | 1.517 (8) | C15—H15A | 0.9700 |
C24'—H24D | 0.9600 | C15—H15B | 0.9700 |
C24'—H24E | 0.9600 | C17—C18 | 1.341 (6) |
C24'—H24F | 0.9600 | C17—H17 | 0.9300 |
N1—C11 | 1.293 (4) | C18—C19 | 1.483 (7) |
N1—C13 | 1.391 (5) | C19—H19A | 0.9600 |
N2—C16 | 1.289 (5) | C19—H19B | 0.9600 |
N2—C18 | 1.388 (5) | C19—H19C | 0.9600 |
C1—C6 | 1.392 (5) | C20—H20A | 0.9700 |
C1—C2 | 1.399 (5) | C20—H20B | 0.9700 |
C11—S1—C10 | 98.84 (19) | C4—C8—H8A | 109.5 |
C12—S2—C11 | 88.3 (2) | C4—C8—H8B | 109.5 |
C16—S3—C15 | 99.1 (2) | H8A—C8—H8B | 109.5 |
C17—S4—C16 | 88.1 (3) | C4—C8—H8C | 109.5 |
C21—S5—C21' | 7 (2) | H8A—C8—H8C | 109.5 |
C21—S5—C20 | 100.4 (5) | H8B—C8—H8C | 109.5 |
C21'—S5—C20 | 102.8 (4) | C2—C9—H9A | 109.5 |
C21—S6—C22 | 88.1 (6) | C2—C9—H9B | 109.5 |
N3—C21—S6 | 116.6 (7) | H9A—C9—H9B | 109.5 |
N3—C21—S5 | 128.1 (11) | C2—C9—H9C | 109.5 |
S6—C21—S5 | 115.2 (8) | H9A—C9—H9C | 109.5 |
C23—C22—S6 | 111.2 (8) | H9B—C9—H9C | 109.5 |
C23—C22—H22 | 124.4 | C1—C10—S1 | 111.4 (3) |
S6—C22—H22 | 124.4 | C1—C10—H10A | 109.3 |
C22—C23—N3 | 115.1 (8) | S1—C10—H10A | 109.3 |
C22—C23—C24 | 127.2 (10) | C1—C10—H10B | 109.3 |
N3—C23—C24 | 117.7 (10) | S1—C10—H10B | 109.3 |
C21—N3—C23 | 109.0 (8) | H10A—C10—H10B | 108.0 |
C22'—S6'—C21' | 89.3 (5) | N1—C11—S2 | 115.9 (3) |
N3'—C21'—S6' | 115.1 (7) | N1—C11—S1 | 124.2 (3) |
N3'—C21'—S5 | 122.7 (9) | S2—C11—S1 | 119.9 (3) |
S6'—C21'—S5 | 122.2 (7) | C13—C12—S2 | 111.2 (3) |
C23'—C22'—S6' | 110.2 (7) | C13—C12—H12 | 124.4 |
C23'—C22'—H22A | 124.9 | S2—C12—H12 | 124.4 |
S6'—C22'—H22A | 124.9 | C12—C13—N1 | 115.3 (4) |
C22'—C23'—N3' | 115.8 (7) | C12—C13—C14 | 127.7 (4) |
C22'—C23'—C24' | 126.6 (9) | N1—C13—C14 | 117.0 (5) |
N3'—C23'—C24' | 117.6 (8) | C13—C14—H14A | 109.5 |
C21'—N3'—C23' | 109.7 (7) | C13—C14—H14B | 109.5 |
C23'—C24'—H24D | 109.5 | H14A—C14—H14B | 109.5 |
C23'—C24'—H24E | 109.5 | C13—C14—H14C | 109.5 |
H24D—C24'—H24E | 109.5 | H14A—C14—H14C | 109.5 |
C23'—C24'—H24F | 109.5 | H14B—C14—H14C | 109.5 |
H24D—C24'—H24F | 109.5 | C5—C15—S3 | 111.2 (3) |
H24E—C24'—H24F | 109.5 | C5—C15—H15A | 109.4 |
C11—N1—C13 | 109.3 (4) | S3—C15—H15A | 109.4 |
C16—N2—C18 | 111.1 (4) | C5—C15—H15B | 109.4 |
C6—C1—C2 | 120.4 (4) | S3—C15—H15B | 109.4 |
C6—C1—C10 | 119.4 (4) | H15A—C15—H15B | 108.0 |
C2—C1—C10 | 120.1 (4) | N2—C16—S4 | 115.2 (3) |
C3—C2—C1 | 119.3 (3) | N2—C16—S3 | 125.6 (3) |
C3—C2—C9 | 120.0 (4) | S4—C16—S3 | 119.2 (3) |
C1—C2—C9 | 120.7 (4) | C18—C17—S4 | 112.1 (4) |
C2—C3—C4 | 120.8 (3) | C18—C17—H17 | 123.9 |
C2—C3—C20 | 119.1 (3) | S4—C17—H17 | 123.9 |
C4—C3—C20 | 120.1 (4) | C17—C18—N2 | 113.4 (5) |
C5—C4—C3 | 119.1 (4) | C17—C18—C19 | 126.9 (5) |
C5—C4—C8 | 120.3 (3) | N2—C18—C19 | 119.7 (5) |
C3—C4—C8 | 120.6 (4) | C18—C19—H19A | 109.5 |
C6—C5—C4 | 120.5 (3) | C18—C19—H19B | 109.5 |
C6—C5—C15 | 120.0 (4) | H19A—C19—H19B | 109.5 |
C4—C5—C15 | 119.4 (4) | C18—C19—H19C | 109.5 |
C1—C6—C5 | 119.7 (3) | H19A—C19—H19C | 109.5 |
C1—C6—C7 | 120.5 (4) | H19B—C19—H19C | 109.5 |
C5—C6—C7 | 119.8 (4) | C3—C20—S5 | 107.4 (2) |
C6—C7—H7A | 109.5 | C3—C20—H20A | 110.2 |
C6—C7—H7B | 109.5 | S5—C20—H20A | 110.2 |
H7A—C7—H7B | 109.5 | C3—C20—H20B | 110.2 |
C6—C7—H7C | 109.5 | S5—C20—H20B | 110.2 |
H7A—C7—H7C | 109.5 | H20A—C20—H20B | 108.5 |
H7B—C7—H7C | 109.5 | ||
C22—S6—C21—N3 | 0.02 (17) | C8—C4—C5—C15 | −6.1 (5) |
C22—S6—C21—S5 | −176 (2) | C2—C1—C6—C5 | −4.2 (5) |
C21'—S5—C21—N3 | −89 (8) | C10—C1—C6—C5 | 172.9 (3) |
C20—S5—C21—N3 | 22.8 (14) | C2—C1—C6—C7 | 176.5 (4) |
C21'—S5—C21—S6 | 87 (7) | C10—C1—C6—C7 | −6.5 (5) |
C20—S5—C21—S6 | −161.7 (16) | C4—C5—C6—C1 | 3.6 (6) |
C21—S6—C22—C23 | 0.03 (16) | C15—C5—C6—C1 | −173.3 (3) |
S6—C22—C23—N3 | −0.1 (3) | C4—C5—C6—C7 | −177.1 (4) |
S6—C22—C23—C24 | −179.9 (3) | C15—C5—C6—C7 | 6.1 (5) |
S6—C21—N3—C23 | −0.1 (3) | C6—C1—C10—S1 | 89.9 (4) |
S5—C21—N3—C23 | 175 (3) | C2—C1—C10—S1 | −93.0 (4) |
C22—C23—N3—C21 | 0.1 (4) | C11—S1—C10—C1 | 166.6 (3) |
C24—C23—N3—C21 | 179.9 (3) | C13—N1—C11—S2 | 0.2 (4) |
C22'—S6'—C21'—N3' | 0.02 (17) | C13—N1—C11—S1 | −179.3 (3) |
C22'—S6'—C21'—S5 | 178 (2) | C12—S2—C11—N1 | 0.5 (3) |
C21—S5—C21'—N3' | 70 (7) | C12—S2—C11—S1 | 179.9 (3) |
C20—S5—C21'—N3' | 0.0 (11) | C10—S1—C11—N1 | −1.1 (4) |
C21—S5—C21'—S6' | −108 (8) | C10—S1—C11—S2 | 179.5 (2) |
C20—S5—C21'—S6' | −178.2 (16) | C11—S2—C12—C13 | −1.0 (3) |
C21'—S6'—C22'—C23' | 0.05 (15) | S2—C12—C13—N1 | 1.3 (5) |
S6'—C22'—C23'—N3' | −0.1 (3) | S2—C12—C13—C14 | −179.6 (4) |
S6'—C22'—C23'—C24' | −179.9 (3) | C11—N1—C13—C12 | −1.0 (5) |
S6'—C21'—N3'—C23' | −0.1 (3) | C11—N1—C13—C14 | 179.9 (4) |
S5—C21'—N3'—C23' | −178 (2) | C6—C5—C15—S3 | −92.4 (4) |
C22'—C23'—N3'—C21' | 0.1 (4) | C4—C5—C15—S3 | 90.7 (4) |
C24'—C23'—N3'—C21' | 179.9 (3) | C16—S3—C15—C5 | 173.7 (3) |
C6—C1—C2—C3 | 3.5 (5) | C18—N2—C16—S4 | −0.1 (5) |
C10—C1—C2—C3 | −173.5 (3) | C18—N2—C16—S3 | −178.2 (3) |
C6—C1—C2—C9 | −174.2 (3) | C17—S4—C16—N2 | −0.2 (4) |
C10—C1—C2—C9 | 8.8 (5) | C17—S4—C16—S3 | 178.1 (3) |
C1—C2—C3—C4 | −2.3 (5) | C15—S3—C16—N2 | 1.7 (5) |
C9—C2—C3—C4 | 175.5 (3) | C15—S3—C16—S4 | −176.3 (3) |
C1—C2—C3—C20 | 177.8 (3) | C16—S4—C17—C18 | 0.4 (4) |
C9—C2—C3—C20 | −4.5 (5) | S4—C17—C18—N2 | −0.6 (6) |
C2—C3—C4—C5 | 1.6 (5) | S4—C17—C18—C19 | 178.2 (4) |
C20—C3—C4—C5 | −178.4 (3) | C16—N2—C18—C17 | 0.4 (6) |
C2—C3—C4—C8 | −177.7 (3) | C16—N2—C18—C19 | −178.5 (4) |
C20—C3—C4—C8 | 2.2 (5) | C2—C3—C20—S5 | 92.4 (4) |
C3—C4—C5—C6 | −2.3 (5) | C4—C3—C20—S5 | −87.6 (4) |
C8—C4—C5—C6 | 177.1 (4) | C21—S5—C20—C3 | −164.4 (11) |
C3—C4—C5—C15 | 174.6 (3) | C21'—S5—C20—C3 | −157.9 (10) |
Experimental details
Crystal data | |
Chemical formula | C24H27N3S6 |
Mr | 549.91 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 12.216 (4), 17.801 (5), 12.528 (4) |
β (°) | 93.420 (6) |
V (Å3) | 2719.4 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.25 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.880, 0.927 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12608, 4780, 2335 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.114, 1.00 |
No. of reflections | 4772 |
No. of parameters | 360 |
No. of restraints | 252 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.19 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.
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We were presently involved in the synthesis of the multithiazoles, because thiazole and its derivatives are of considerable interest due to the fact that they exhibit remarkable bioactivities (Tian et al., 1996; Sasaki, 1994, 1996) and act as potential donors to transition metals for the generation of one-, two- and three-dimensional coordination networks (Liu et al., 2001; Sun et al., 1997; Fisher et al., 1985). Thus, we were prompted to explore new compounds containing two or more thiazolyl groups using different linkages. The selection of the linkages is crucial; the existing functions of linkages and the availability of the starting materials from commercial sources are two aspects of primary consideration. Herein we report the synthesis and the structure of a new flexible ligand containing three thiazolyl groups, namely 2,4,6-trimethyl-1,3,5-tris(4-methylthiazol-2-ylsulfanylmethyl)benzene, (I).
As shown in Fig. 1, the tripodal arrangement of all 4-methylthiazol-2-ylsulfanyl groups gives a conformation with all S atoms ready for facile coordination with a metal ion. The methyl and methylene groups bonded to the benzene ring are nearly coplanar with the benzene plane, with the largest deviation of 0.1504 (8) Å for atom C10. Similar situations have been found between the methyl groups and the bonded thiazole rings in the 4-methylthiazol-2-yl groups. Three exocyclic S atoms (viz. S1, S3 and S5) are approximately equidistant from the benzene ring, forming an angle of 2.2 (9)° between plane defined as S1/S3/S5 and the benzene plane.