Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801005116/cv6014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801005116/cv6014Isup2.hkl |
CCDC reference: 162834
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.061
- wR factor = 0.142
- Data-to-parameter ratio = 14.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_320 Alert C Check Hybridisation of S(8) in main residue ? PLAT_320 Alert C Check Hybridisation of S(20) in main residue ? PLAT_320 Alert C Check Hybridisation of S(35) in main residue ? PLAT_320 Alert C Check Hybridisation of S(47) in main residue ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check
The preparation of (I) followed the general procedure previously reported by Cho, Park, Hwang et al. (1999). The details will be reported elsewhere.
All H atoms were placed in calculated positions [C—Hmethylene = 0.97 Å and C—Haromatic = 0.93 Å], with Uiso constrained to be 1.2 times the equivalent isotropic displacement parameter of the attached C atom. The highest peak and the deepest hole in the final difference density map are at 0.81 Å from H40 and 0.96 Å from S35, respectively.
Data collection: CAD-4 EXPRESS (Enraf-Nonious, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H16N4O3S4 | F(000) = 1824 |
Mr = 440.57 | Dx = 1.475 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 16.827 (2) Å | Cell parameters from 25 reflections |
b = 14.1071 (16) Å | θ = 11.3–12.7° |
c = 16.760 (4) Å | µ = 0.50 mm−1 |
β = 93.950 (16)° | T = 293 K |
V = 3969.0 (12) Å3 | Plate, light brown |
Z = 8 | 0.50 × 0.43 × 0.13 mm |
Enraf-Nonious CAD4 diffractometer | 3946 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
non–profiled ω/2θ scans | h = 0→19 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→16 |
Tmin = 0.779, Tmax = 0.936 | l = −19→19 |
7087 measured reflections | 3 standard reflections every 300 min |
6845 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0505P)2 + 1.381P] where P = (Fo2 + 2Fc2)/3 |
6845 reflections | (Δ/σ)max < 0.001 |
481 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C16H16N4O3S4 | V = 3969.0 (12) Å3 |
Mr = 440.57 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.827 (2) Å | µ = 0.50 mm−1 |
b = 14.1071 (16) Å | T = 293 K |
c = 16.760 (4) Å | 0.50 × 0.43 × 0.13 mm |
β = 93.950 (16)° |
Enraf-Nonious CAD4 diffractometer | 3946 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.028 |
Tmin = 0.779, Tmax = 0.936 | 3 standard reflections every 300 min |
7087 measured reflections | intensity decay: none |
6845 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.95 e Å−3 |
6845 reflections | Δρmin = −0.27 e Å−3 |
481 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9779 (3) | 0.8437 (4) | 0.3458 (3) | 0.0558 (14) | |
H1A | 0.9569 | 0.8534 | 0.3976 | 0.067* | |
H1B | 1.0309 | 0.8710 | 0.3475 | 0.067* | |
C2 | 0.9832 (3) | 0.7395 (4) | 0.3298 (3) | 0.0569 (14) | |
H2A | 0.9945 | 0.7286 | 0.2745 | 0.068* | |
H2B | 1.0257 | 0.7115 | 0.3640 | 0.068* | |
O3 | 0.90958 (18) | 0.6985 (2) | 0.34540 (18) | 0.0503 (9) | |
C4 | 0.9014 (3) | 0.6031 (3) | 0.3213 (3) | 0.0527 (14) | |
H4A | 0.9403 | 0.5639 | 0.3513 | 0.063* | |
H4B | 0.9096 | 0.5970 | 0.2648 | 0.063* | |
C5 | 0.8184 (3) | 0.5731 (3) | 0.3375 (3) | 0.0544 (14) | |
H5A | 0.8109 | 0.5068 | 0.3234 | 0.065* | |
H5B | 0.8108 | 0.5800 | 0.3940 | 0.065* | |
N6 | 0.7600 (2) | 0.6306 (3) | 0.2911 (2) | 0.0452 (10) | |
C7 | 0.7144 (3) | 0.6972 (4) | 0.3227 (3) | 0.0529 (14) | |
S8 | 0.66391 (8) | 0.75875 (11) | 0.24110 (8) | 0.0623 (4) | |
C9 | 0.7106 (3) | 0.6848 (3) | 0.1758 (3) | 0.0412 (12) | |
S10 | 0.69014 (8) | 0.70025 (10) | 0.07307 (7) | 0.0559 (4) | |
C11 | 0.7601 (3) | 0.6182 (3) | 0.0326 (3) | 0.0507 (13) | |
H11A | 0.7506 | 0.5554 | 0.0536 | 0.061* | |
H11B | 0.7497 | 0.6155 | −0.0250 | 0.061* | |
C12 | 0.8464 (3) | 0.6430 (3) | 0.0510 (2) | 0.0402 (12) | |
C13 | 0.8998 (3) | 0.5740 (4) | 0.0772 (3) | 0.0649 (16) | |
H13 | 0.8823 | 0.5122 | 0.0842 | 0.078* | |
C14 | 0.9785 (4) | 0.5957 (4) | 0.0930 (4) | 0.0775 (19) | |
H14 | 1.0144 | 0.5485 | 0.1098 | 0.093* | |
C15 | 1.0049 (3) | 0.6879 (4) | 0.0842 (3) | 0.0651 (16) | |
H15 | 1.0581 | 0.7025 | 0.0970 | 0.078* | |
C16 | 0.9533 (3) | 0.7575 (3) | 0.0568 (2) | 0.0415 (12) | |
C17 | 0.9845 (3) | 0.8556 (3) | 0.0443 (3) | 0.0496 (13) | |
H17A | 1.0015 | 0.8599 | −0.0097 | 0.059* | |
H17B | 1.0312 | 0.8651 | 0.0807 | 0.059* | |
S18 | 0.91533 (8) | 0.95059 (9) | 0.05893 (7) | 0.0503 (4) | |
C19 | 0.9015 (3) | 0.9344 (3) | 0.1604 (3) | 0.0409 (12) | |
S20 | 0.81373 (9) | 0.96650 (12) | 0.20013 (9) | 0.0764 (5) | |
C21 | 0.8530 (4) | 0.9240 (4) | 0.2954 (3) | 0.0609 (15) | |
N22 | 0.9270 (3) | 0.8918 (3) | 0.2847 (2) | 0.0479 (11) | |
N23 | 0.9545 (2) | 0.8971 (3) | 0.2091 (2) | 0.0467 (10) | |
N24 | 0.7585 (2) | 0.6232 (3) | 0.2083 (2) | 0.0428 (10) | |
O25 | 0.7076 (2) | 0.7125 (3) | 0.3933 (2) | 0.0750 (12) | |
O26 | 0.8193 (3) | 0.9255 (3) | 0.3567 (2) | 0.0982 (15) | |
C27 | 0.8746 (3) | 0.7340 (3) | 0.0394 (2) | 0.0413 (12) | |
H27 | 0.8394 | 0.7803 | 0.0192 | 0.050* | |
C28 | 0.4713 (3) | 0.8310 (4) | 0.1179 (3) | 0.0570 (14) | |
H28A | 0.4569 | 0.8472 | 0.1713 | 0.068* | |
H28B | 0.5286 | 0.8383 | 0.1166 | 0.068* | |
C29 | 0.4492 (3) | 0.7300 (4) | 0.1004 (3) | 0.0624 (15) | |
H29A | 0.4591 | 0.7144 | 0.0455 | 0.075* | |
H29B | 0.4808 | 0.6879 | 0.1356 | 0.075* | |
O30 | 0.3676 (2) | 0.7192 (3) | 0.1124 (2) | 0.0624 (10) | |
C31 | 0.3376 (4) | 0.6275 (4) | 0.0969 (3) | 0.0685 (17) | |
H31A | 0.3566 | 0.5844 | 0.1391 | 0.082* | |
H31B | 0.3551 | 0.6042 | 0.0465 | 0.082* | |
C32 | 0.2481 (3) | 0.6335 (4) | 0.0932 (3) | 0.0639 (16) | |
H32A | 0.2254 | 0.5706 | 0.0860 | 0.077* | |
H32B | 0.2312 | 0.6594 | 0.1429 | 0.077* | |
N33 | 0.2202 (2) | 0.6938 (3) | 0.0269 (2) | 0.0513 (11) | |
C34 | 0.2022 (3) | 0.7869 (4) | 0.0352 (3) | 0.0506 (13) | |
S35 | 0.18850 (9) | 0.83401 (10) | −0.06286 (8) | 0.0603 (4) | |
C36 | 0.2051 (3) | 0.7236 (4) | −0.1019 (3) | 0.0445 (12) | |
S37 | 0.19962 (8) | 0.70638 (11) | −0.20473 (8) | 0.0589 (4) | |
C38 | 0.27612 (19) | 0.6185 (2) | −0.21458 (17) | 0.0544 (14) | |
H38A | 0.2607 | 0.5611 | −0.1878 | 0.065* | |
H38B | 0.2786 | 0.6037 | −0.2709 | 0.065* | |
C39 | 0.35807 (19) | 0.6468 (2) | −0.18132 (17) | 0.0472 (13) | |
C40 | 0.40722 (19) | 0.5802 (2) | −0.14189 (17) | 0.0678 (16) | |
H40 | 0.3894 | 0.5187 | −0.1341 | 0.081* | |
C41 | 0.4820 (4) | 0.6070 (5) | −0.1149 (4) | 0.0787 (18) | |
H41 | 0.5152 | 0.5621 | −0.0891 | 0.094* | |
C42 | 0.5109 (3) | 0.6974 (5) | −0.1240 (3) | 0.0677 (17) | |
H42 | 0.5621 | 0.7138 | −0.1042 | 0.081* | |
C43 | 0.4614 (3) | 0.7636 (4) | −0.1636 (3) | 0.0526 (14) | |
C44 | 0.4913 (3) | 0.8626 (4) | −0.1757 (3) | 0.0659 (16) | |
H44A | 0.5099 | 0.8670 | −0.2291 | 0.079* | |
H44B | 0.5366 | 0.8736 | −0.1380 | 0.079* | |
S45 | 0.41895 (9) | 0.95576 (10) | −0.16392 (8) | 0.0656 (4) | |
C46 | 0.4096 (3) | 0.9471 (4) | −0.0612 (3) | 0.0480 (13) | |
S47 | 0.34723 (8) | 1.02134 (10) | −0.01205 (8) | 0.0576 (4) | |
C48 | 0.3789 (3) | 0.9635 (4) | 0.0796 (3) | 0.0504 (13) | |
N49 | 0.4318 (2) | 0.8954 (3) | 0.0607 (2) | 0.0474 (10) | |
N50 | 0.4498 (2) | 0.8871 (3) | −0.0177 (2) | 0.0472 (10) | |
N51 | 0.2217 (2) | 0.6583 (3) | −0.0495 (2) | 0.0495 (11) | |
O52 | 0.1957 (2) | 0.8305 (3) | 0.0971 (2) | 0.0716 (11) | |
O53 | 0.3582 (2) | 0.9832 (3) | 0.1449 (2) | 0.0656 (10) | |
C54 | 0.3866 (3) | 0.7372 (4) | −0.1920 (3) | 0.0477 (13) | |
H54 | 0.3540 | 0.7815 | −0.2192 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.059 (3) | 0.067 (4) | 0.040 (3) | −0.016 (3) | −0.002 (3) | 0.011 (3) |
C2 | 0.048 (3) | 0.064 (4) | 0.058 (3) | 0.000 (3) | −0.006 (3) | 0.015 (3) |
O3 | 0.046 (2) | 0.046 (2) | 0.059 (2) | −0.0066 (17) | 0.0049 (17) | −0.0053 (17) |
C4 | 0.063 (4) | 0.039 (3) | 0.055 (3) | 0.010 (3) | −0.007 (3) | 0.001 (3) |
C5 | 0.073 (4) | 0.043 (3) | 0.044 (3) | −0.013 (3) | −0.017 (3) | 0.010 (2) |
N6 | 0.049 (3) | 0.053 (3) | 0.032 (2) | −0.013 (2) | −0.0006 (19) | 0.006 (2) |
C7 | 0.046 (3) | 0.076 (4) | 0.037 (3) | −0.008 (3) | 0.008 (2) | −0.002 (3) |
S8 | 0.0586 (9) | 0.0836 (11) | 0.0453 (8) | 0.0157 (8) | 0.0077 (7) | −0.0027 (7) |
C9 | 0.040 (3) | 0.049 (3) | 0.035 (3) | −0.008 (2) | 0.004 (2) | 0.002 (2) |
S10 | 0.0572 (8) | 0.0766 (10) | 0.0335 (7) | 0.0077 (8) | 0.0004 (6) | 0.0090 (7) |
C11 | 0.061 (3) | 0.057 (3) | 0.034 (3) | −0.009 (3) | 0.005 (2) | −0.002 (2) |
C12 | 0.051 (3) | 0.044 (3) | 0.026 (2) | 0.003 (3) | 0.009 (2) | 0.003 (2) |
C13 | 0.069 (4) | 0.040 (3) | 0.088 (4) | −0.002 (3) | 0.020 (3) | 0.007 (3) |
C14 | 0.067 (4) | 0.044 (4) | 0.121 (6) | 0.012 (3) | 0.008 (4) | 0.025 (4) |
C15 | 0.051 (3) | 0.062 (4) | 0.083 (4) | −0.002 (3) | 0.009 (3) | 0.010 (3) |
C16 | 0.054 (3) | 0.041 (3) | 0.031 (3) | 0.005 (3) | 0.013 (2) | 0.001 (2) |
C17 | 0.064 (3) | 0.047 (3) | 0.040 (3) | −0.002 (3) | 0.017 (2) | 0.002 (2) |
S18 | 0.0730 (9) | 0.0403 (7) | 0.0388 (7) | 0.0019 (7) | 0.0124 (6) | 0.0069 (6) |
C19 | 0.048 (3) | 0.035 (3) | 0.041 (3) | −0.005 (2) | 0.011 (2) | −0.002 (2) |
S20 | 0.0772 (11) | 0.0910 (12) | 0.0645 (10) | 0.0343 (9) | 0.0289 (8) | 0.0283 (9) |
C21 | 0.085 (4) | 0.050 (4) | 0.051 (3) | 0.017 (3) | 0.027 (3) | 0.004 (3) |
N22 | 0.069 (3) | 0.042 (3) | 0.033 (2) | −0.005 (2) | 0.003 (2) | 0.0022 (19) |
N23 | 0.052 (3) | 0.053 (3) | 0.036 (2) | −0.004 (2) | 0.011 (2) | 0.000 (2) |
N24 | 0.052 (3) | 0.048 (3) | 0.028 (2) | −0.006 (2) | 0.0004 (18) | 0.0014 (19) |
O25 | 0.076 (3) | 0.112 (3) | 0.037 (2) | −0.002 (2) | 0.0075 (19) | −0.009 (2) |
O26 | 0.141 (4) | 0.096 (3) | 0.065 (3) | 0.045 (3) | 0.062 (3) | 0.018 (2) |
C27 | 0.057 (3) | 0.037 (3) | 0.031 (3) | 0.009 (3) | 0.009 (2) | 0.005 (2) |
C28 | 0.060 (4) | 0.067 (4) | 0.043 (3) | −0.001 (3) | 0.004 (3) | 0.004 (3) |
C29 | 0.070 (4) | 0.067 (4) | 0.050 (3) | 0.014 (3) | 0.003 (3) | 0.009 (3) |
O30 | 0.076 (3) | 0.055 (2) | 0.056 (2) | −0.004 (2) | 0.007 (2) | −0.0089 (18) |
C31 | 0.104 (5) | 0.049 (4) | 0.052 (3) | 0.005 (4) | −0.006 (3) | 0.006 (3) |
C32 | 0.093 (5) | 0.057 (4) | 0.043 (3) | −0.019 (3) | 0.014 (3) | 0.007 (3) |
N33 | 0.069 (3) | 0.048 (3) | 0.037 (2) | −0.007 (2) | 0.008 (2) | −0.005 (2) |
C34 | 0.047 (3) | 0.059 (4) | 0.045 (3) | 0.002 (3) | 0.006 (2) | −0.010 (3) |
S35 | 0.0699 (10) | 0.0512 (9) | 0.0586 (9) | 0.0087 (8) | −0.0046 (7) | −0.0067 (7) |
C36 | 0.037 (3) | 0.055 (3) | 0.041 (3) | −0.012 (3) | 0.004 (2) | −0.003 (3) |
S37 | 0.0575 (9) | 0.0796 (10) | 0.0396 (7) | −0.0021 (8) | 0.0028 (6) | −0.0057 (7) |
C38 | 0.061 (4) | 0.059 (3) | 0.045 (3) | −0.015 (3) | 0.014 (3) | −0.016 (3) |
C39 | 0.056 (3) | 0.050 (3) | 0.037 (3) | 0.002 (3) | 0.011 (2) | −0.011 (2) |
C40 | 0.070 (4) | 0.065 (4) | 0.070 (4) | −0.001 (3) | 0.020 (3) | −0.005 (3) |
C41 | 0.079 (5) | 0.074 (5) | 0.084 (5) | 0.015 (4) | 0.009 (4) | 0.003 (4) |
C42 | 0.045 (3) | 0.098 (5) | 0.061 (4) | −0.001 (4) | 0.009 (3) | −0.014 (4) |
C43 | 0.056 (4) | 0.061 (4) | 0.041 (3) | −0.008 (3) | 0.010 (3) | −0.016 (3) |
C44 | 0.071 (4) | 0.080 (4) | 0.048 (3) | −0.018 (3) | 0.020 (3) | −0.018 (3) |
S45 | 0.0924 (11) | 0.0623 (10) | 0.0416 (8) | −0.0188 (9) | 0.0023 (7) | 0.0044 (7) |
C46 | 0.048 (3) | 0.052 (3) | 0.044 (3) | −0.011 (3) | −0.003 (2) | −0.002 (3) |
S47 | 0.0565 (9) | 0.0534 (9) | 0.0629 (9) | 0.0022 (7) | 0.0037 (7) | 0.0059 (7) |
C48 | 0.048 (3) | 0.050 (3) | 0.053 (3) | −0.015 (3) | 0.007 (3) | −0.001 (3) |
N49 | 0.050 (3) | 0.052 (3) | 0.040 (2) | 0.005 (2) | 0.004 (2) | 0.000 (2) |
N50 | 0.048 (3) | 0.057 (3) | 0.037 (2) | −0.003 (2) | 0.0082 (19) | −0.001 (2) |
N51 | 0.062 (3) | 0.048 (3) | 0.040 (2) | −0.008 (2) | 0.011 (2) | −0.011 (2) |
O52 | 0.081 (3) | 0.076 (3) | 0.058 (2) | 0.006 (2) | 0.006 (2) | −0.032 (2) |
O53 | 0.073 (3) | 0.070 (3) | 0.057 (2) | −0.002 (2) | 0.027 (2) | −0.006 (2) |
C54 | 0.056 (3) | 0.053 (3) | 0.035 (3) | −0.004 (3) | 0.011 (2) | −0.005 (2) |
C1—N22 | 1.456 (6) | C28—N49 | 1.449 (6) |
C1—C2 | 1.497 (7) | C28—C29 | 1.498 (7) |
C1—H1A | 0.9700 | C28—H28A | 0.9700 |
C1—H1B | 0.9700 | C28—H28B | 0.9700 |
C2—O3 | 1.409 (5) | C29—O30 | 1.411 (6) |
C2—H2A | 0.9700 | C29—H29A | 0.9700 |
C2—H2B | 0.9700 | C29—H29B | 0.9700 |
O3—C4 | 1.409 (5) | O30—C31 | 1.407 (6) |
C4—C5 | 1.501 (6) | C31—C32 | 1.505 (7) |
C4—H4A | 0.9700 | C31—H31A | 0.9700 |
C4—H4B | 0.9700 | C31—H31B | 0.9700 |
C5—N6 | 1.458 (5) | C32—N33 | 1.450 (6) |
C5—H5A | 0.9700 | C32—H32A | 0.9700 |
C5—H5B | 0.9700 | C32—H32B | 0.9700 |
N6—C7 | 1.344 (6) | N33—C34 | 1.357 (6) |
N6—N24 | 1.390 (5) | N33—N51 | 1.376 (5) |
C7—O25 | 1.216 (5) | C34—O52 | 1.218 (5) |
C7—S8 | 1.785 (5) | C34—S35 | 1.773 (5) |
S8—C9 | 1.738 (5) | S35—C36 | 1.720 (5) |
C9—N24 | 1.281 (5) | C36—N51 | 1.290 (6) |
C9—S10 | 1.746 (5) | C36—S37 | 1.736 (5) |
S10—C11 | 1.815 (5) | S37—C38 | 1.803 (4) |
C11—C12 | 1.504 (6) | C38—C39 | 1.5049 |
C11—H11A | 0.9700 | C38—H38A | 0.9700 |
C11—H11B | 0.9700 | C38—H38B | 0.9700 |
C12—C13 | 1.376 (6) | C39—C54 | 1.379 (5) |
C12—C27 | 1.388 (6) | C39—C40 | 1.3882 |
C13—C14 | 1.366 (7) | C40—C41 | 1.362 (7) |
C13—H13 | 0.9300 | C40—H40 | 0.9300 |
C14—C15 | 1.384 (7) | C41—C42 | 1.378 (8) |
C14—H14 | 0.9300 | C41—H41 | 0.9300 |
C15—C16 | 1.369 (6) | C42—C43 | 1.389 (7) |
C15—H15 | 0.9300 | C42—H42 | 0.9300 |
C16—C27 | 1.377 (6) | C43—C54 | 1.367 (6) |
C16—C17 | 1.500 (6) | C43—C44 | 1.503 (7) |
C17—S18 | 1.802 (5) | C44—S45 | 1.811 (5) |
C17—H17A | 0.9700 | C44—H44A | 0.9700 |
C17—H17B | 0.9700 | C44—H44B | 0.9700 |
S18—C19 | 1.747 (5) | S45—C46 | 1.743 (5) |
C19—N23 | 1.279 (5) | C46—N50 | 1.280 (6) |
C19—S20 | 1.723 (5) | C46—S47 | 1.731 (5) |
S20—C21 | 1.790 (5) | S47—C48 | 1.788 (5) |
C21—O26 | 1.207 (5) | C48—O53 | 1.203 (5) |
C21—N22 | 1.349 (6) | C48—N49 | 1.361 (6) |
N22—N23 | 1.382 (5) | N49—N50 | 1.375 (5) |
C27—H27 | 0.9300 | C54—H54 | 0.9300 |
N22—C1—C2 | 111.8 (4) | N49—C28—C29 | 111.7 (4) |
N22—C1—H1A | 109.2 | N49—C28—H28A | 109.3 |
C2—C1—H1A | 109.2 | C29—C28—H28A | 109.3 |
N22—C1—H1B | 109.2 | N49—C28—H28B | 109.3 |
C2—C1—H1B | 109.2 | C29—C28—H28B | 109.3 |
H1A—C1—H1B | 107.9 | H28A—C28—H28B | 107.9 |
O3—C2—C1 | 107.8 (4) | O30—C29—C28 | 107.8 (4) |
O3—C2—H2A | 110.1 | O30—C29—H29A | 110.1 |
C1—C2—H2A | 110.1 | C28—C29—H29A | 110.1 |
O3—C2—H2B | 110.1 | O30—C29—H29B | 110.1 |
C1—C2—H2B | 110.1 | C28—C29—H29B | 110.1 |
H2A—C2—H2B | 108.5 | H29A—C29—H29B | 108.5 |
C4—O3—C2 | 114.1 (4) | C31—O30—C29 | 114.4 (4) |
O3—C4—C5 | 106.9 (4) | O30—C31—C32 | 107.5 (5) |
O3—C4—H4A | 110.3 | O30—C31—H31A | 110.2 |
C5—C4—H4A | 110.3 | C32—C31—H31A | 110.2 |
O3—C4—H4B | 110.3 | O30—C31—H31B | 110.2 |
C5—C4—H4B | 110.3 | C32—C31—H31B | 110.2 |
H4A—C4—H4B | 108.6 | H31A—C31—H31B | 108.5 |
N6—C5—C4 | 110.3 (4) | N33—C32—C31 | 109.6 (4) |
N6—C5—H5A | 109.6 | N33—C32—H32A | 109.8 |
C4—C5—H5A | 109.6 | C31—C32—H32A | 109.8 |
N6—C5—H5B | 109.6 | N33—C32—H32B | 109.8 |
C4—C5—H5B | 109.6 | C31—C32—H32B | 109.8 |
H5A—C5—H5B | 108.1 | H32A—C32—H32B | 108.2 |
C7—N6—N24 | 118.3 (4) | C34—N33—N51 | 117.7 (4) |
C7—N6—C5 | 124.1 (4) | C34—N33—C32 | 123.5 (4) |
N24—N6—C5 | 117.2 (4) | N51—N33—C32 | 118.2 (4) |
O25—C7—N6 | 127.0 (5) | O52—C34—N33 | 127.6 (5) |
O25—C7—S8 | 125.9 (5) | O52—C34—S35 | 125.9 (4) |
N6—C7—S8 | 107.0 (3) | N33—C34—S35 | 106.5 (4) |
C9—S8—C7 | 88.7 (2) | C36—S35—C34 | 89.9 (2) |
N24—C9—S8 | 116.0 (3) | N51—C36—S35 | 114.9 (3) |
N24—C9—S10 | 125.4 (4) | N51—C36—S37 | 124.8 (4) |
S8—C9—S10 | 118.6 (3) | S35—C36—S37 | 120.3 (3) |
C9—S10—C11 | 101.5 (2) | C36—S37—C38 | 101.4 (2) |
C12—C11—S10 | 114.7 (3) | C39—C38—S37 | 115.22 (11) |
C12—C11—H11A | 108.6 | C39—C38—H38A | 108.5 |
S10—C11—H11A | 108.6 | S37—C38—H38A | 108.5 |
C12—C11—H11B | 108.6 | C39—C38—H38B | 108.5 |
S10—C11—H11B | 108.6 | S37—C38—H38B | 108.5 |
H11A—C11—H11B | 107.6 | H38A—C38—H38B | 107.5 |
C13—C12—C27 | 118.4 (5) | C54—C39—C40 | 119.1 (3) |
C13—C12—C11 | 120.1 (5) | C54—C39—C38 | 121.0 (3) |
C27—C12—C11 | 121.4 (4) | C40—C39—C38 | 119.9 |
C14—C13—C12 | 120.5 (5) | C41—C40—C39 | 118.5 (3) |
C14—C13—H13 | 119.8 | C41—C40—H40 | 120.8 |
C12—C13—H13 | 119.8 | C39—C40—H40 | 120.8 |
C13—C14—C15 | 120.2 (5) | C40—C41—C42 | 123.1 (6) |
C13—C14—H14 | 119.9 | C40—C41—H41 | 118.5 |
C15—C14—H14 | 119.9 | C42—C41—H41 | 118.5 |
C16—C15—C14 | 120.6 (5) | C41—C42—C43 | 118.1 (5) |
C16—C15—H15 | 119.7 | C41—C42—H42 | 120.9 |
C14—C15—H15 | 119.7 | C43—C42—H42 | 120.9 |
C15—C16—C27 | 118.4 (5) | C54—C43—C42 | 119.4 (5) |
C15—C16—C17 | 119.3 (5) | C54—C43—C44 | 121.0 (5) |
C27—C16—C17 | 122.2 (4) | C42—C43—C44 | 119.6 (5) |
C16—C17—S18 | 115.6 (3) | C43—C44—S45 | 115.2 (4) |
C16—C17—H17A | 108.4 | C43—C44—H44A | 108.5 |
S18—C17—H17A | 108.4 | S45—C44—H44A | 108.5 |
C16—C17—H17B | 108.4 | C43—C44—H44B | 108.5 |
S18—C17—H17B | 108.4 | S45—C44—H44B | 108.5 |
H17A—C17—H17B | 107.5 | H44A—C44—H44B | 107.5 |
C19—S18—C17 | 99.5 (2) | C46—S45—C44 | 99.4 (2) |
N23—C19—S20 | 116.1 (3) | N50—C46—S47 | 116.3 (4) |
N23—C19—S18 | 122.8 (4) | N50—C46—S45 | 121.9 (4) |
S20—C19—S18 | 121.1 (3) | S47—C46—S45 | 121.8 (3) |
C19—S20—C21 | 89.0 (2) | C46—S47—C48 | 88.8 (2) |
O26—C21—N22 | 127.7 (5) | O53—C48—N49 | 127.5 (5) |
O26—C21—S20 | 125.9 (5) | O53—C48—S47 | 126.0 (4) |
N22—C21—S20 | 106.4 (4) | N49—C48—S47 | 106.4 (4) |
C21—N22—N23 | 118.3 (4) | C48—N49—N50 | 118.3 (4) |
C21—N22—C1 | 124.6 (4) | C48—N49—C28 | 124.5 (4) |
N23—N22—C1 | 116.9 (4) | N50—N49—C28 | 117.2 (4) |
C19—N23—N22 | 110.2 (4) | C46—N50—N49 | 110.2 (4) |
C9—N24—N6 | 109.9 (4) | C36—N51—N33 | 110.9 (4) |
C16—C27—C12 | 121.8 (4) | C43—C54—C39 | 121.8 (5) |
C16—C27—H27 | 119.1 | C43—C54—H54 | 119.1 |
C12—C27—H27 | 119.1 | C39—C54—H54 | 119.1 |
N22—C1—C2—O3 | −72.0 (5) | N49—C28—C29—O30 | −66.1 (5) |
C1—C2—O3—C4 | 170.8 (4) | C28—C29—O30—C31 | 179.0 (4) |
C2—O3—C4—C5 | −176.5 (4) | C29—O30—C31—C32 | −166.6 (4) |
O3—C4—C5—N6 | 61.3 (5) | O30—C31—C32—N33 | 63.2 (5) |
C4—C5—N6—C7 | −108.2 (5) | C31—C32—N33—C34 | −97.0 (6) |
C4—C5—N6—N24 | 64.2 (5) | C31—C32—N33—N51 | 74.5 (5) |
N24—N6—C7—O25 | 178.7 (5) | N51—N33—C34—O52 | 177.7 (5) |
C5—N6—C7—O25 | −9.0 (8) | C32—N33—C34—O52 | −10.8 (8) |
N24—N6—C7—S8 | −0.5 (5) | N51—N33—C34—S35 | −1.6 (5) |
C5—N6—C7—S8 | 171.8 (3) | C32—N33—C34—S35 | 169.9 (4) |
O25—C7—S8—C9 | −178.5 (5) | O52—C34—S35—C36 | −177.5 (5) |
N6—C7—S8—C9 | 0.7 (3) | N33—C34—S35—C36 | 1.9 (4) |
C7—S8—C9—N24 | −1.0 (4) | C34—S35—C36—N51 | −1.9 (4) |
C7—S8—C9—S10 | 179.6 (3) | C34—S35—C36—S37 | 178.4 (3) |
N24—C9—S10—C11 | −5.6 (5) | N51—C36—S37—C38 | −34.6 (4) |
S8—C9—S10—C11 | 173.7 (3) | S35—C36—S37—C38 | 145.1 (3) |
C9—S10—C11—C12 | −64.9 (4) | C36—S37—C38—C39 | −57.73 (18) |
S10—C11—C12—C13 | 134.3 (4) | S37—C38—C39—C54 | −40.8 (2) |
S10—C11—C12—C27 | −48.2 (5) | S37—C38—C39—C40 | 141.63 (11) |
C27—C12—C13—C14 | 1.5 (8) | C54—C39—C40—C41 | 0.2 (3) |
C11—C12—C13—C14 | 179.1 (5) | C38—C39—C40—C41 | 177.7 (3) |
C12—C13—C14—C15 | 1.1 (9) | C39—C40—C41—C42 | 0.9 (7) |
C13—C14—C15—C16 | −2.4 (9) | C40—C41—C42—C43 | −1.0 (8) |
C14—C15—C16—C27 | 0.8 (8) | C41—C42—C43—C54 | 0.0 (8) |
C14—C15—C16—C17 | −177.2 (5) | C41—C42—C43—C44 | −179.1 (5) |
C15—C16—C17—S18 | −149.4 (4) | C54—C43—C44—S45 | 40.0 (6) |
C27—C16—C17—S18 | 32.6 (6) | C42—C43—C44—S45 | −140.8 (4) |
C16—C17—S18—C19 | 63.3 (4) | C43—C44—S45—C46 | 68.8 (4) |
C17—S18—C19—N23 | 27.4 (4) | C44—S45—C46—N50 | 1.1 (5) |
C17—S18—C19—S20 | −151.5 (3) | C44—S45—C46—S47 | 179.3 (3) |
N23—C19—S20—C21 | −0.1 (4) | N50—C46—S47—C48 | −0.5 (4) |
S18—C19—S20—C21 | 178.8 (3) | S45—C46—S47—C48 | −178.8 (3) |
C19—S20—C21—O26 | 179.5 (6) | C46—S47—C48—O53 | 178.0 (5) |
C19—S20—C21—N22 | 0.3 (4) | C46—S47—C48—N49 | −0.4 (3) |
O26—C21—N22—N23 | −179.7 (5) | O53—C48—N49—N50 | −177.1 (5) |
S20—C21—N22—N23 | −0.5 (5) | S47—C48—N49—N50 | 1.3 (5) |
O26—C21—N22—C1 | 6.2 (9) | O53—C48—N49—C28 | 2.3 (8) |
S20—C21—N22—C1 | −174.6 (4) | S47—C48—N49—C28 | −179.3 (4) |
C2—C1—N22—C21 | 106.0 (6) | C29—C28—N49—C48 | 117.2 (5) |
C2—C1—N22—N23 | −68.2 (5) | C29—C28—N49—N50 | −63.4 (6) |
S20—C19—N23—N22 | −0.1 (5) | S47—C46—N50—N49 | 1.2 (5) |
S18—C19—N23—N22 | −179.1 (3) | S45—C46—N50—N49 | 179.5 (3) |
C21—N22—N23—C19 | 0.4 (6) | C48—N49—N50—C46 | −1.6 (6) |
C1—N22—N23—C19 | 175.0 (4) | C28—N49—N50—C46 | 178.9 (4) |
S8—C9—N24—N6 | 0.9 (5) | S35—C36—N51—N33 | 1.3 (5) |
S10—C9—N24—N6 | −179.8 (3) | S37—C36—N51—N33 | −179.0 (3) |
C7—N6—N24—C9 | −0.3 (5) | C34—N33—N51—C36 | 0.3 (6) |
C5—N6—N24—C9 | −173.1 (4) | C32—N33—N51—C36 | −171.7 (4) |
C15—C16—C27—C12 | 1.9 (7) | C42—C43—C54—C39 | 1.0 (7) |
C17—C16—C27—C12 | 179.9 (4) | C44—C43—C54—C39 | −179.9 (4) |
C13—C12—C27—C16 | −3.1 (7) | C40—C39—C54—C43 | −1.1 (5) |
C11—C12—C27—C16 | 179.3 (4) | C38—C39—C54—C43 | −178.6 (3) |
Experimental details
Crystal data | |
Chemical formula | C16H16N4O3S4 |
Mr | 440.57 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.827 (2), 14.1071 (16), 16.760 (4) |
β (°) | 93.950 (16) |
V (Å3) | 3969.0 (12) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.50 × 0.43 × 0.13 |
Data collection | |
Diffractometer | Enraf-Nonious CAD4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.779, 0.936 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7087, 6845, 3946 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.142, 1.02 |
No. of reflections | 6845 |
No. of parameters | 481 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.95, −0.27 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonious, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
C7—O25 | 1.216 (5) | C34—O52 | 1.218 (5) |
C7—S8 | 1.785 (5) | C34—S35 | 1.773 (5) |
S8—C9 | 1.738 (5) | S35—C36 | 1.720 (5) |
C9—S10 | 1.746 (5) | C36—S37 | 1.736 (5) |
S10—C11 | 1.815 (5) | S37—C38 | 1.803 (4) |
C17—S18 | 1.802 (5) | C44—S45 | 1.811 (5) |
S18—C19 | 1.747 (5) | S45—C46 | 1.743 (5) |
C19—S20 | 1.723 (5) | C46—S47 | 1.731 (5) |
S20—C21 | 1.790 (5) | S47—C48 | 1.788 (5) |
C21—O26 | 1.207 (5) | C48—O53 | 1.203 (5) |
C9—S8—C7 | 88.7 (2) | C36—S35—C34 | 89.9 (2) |
C19—S20—C21 | 89.0 (2) | C46—S47—C48 | 88.8 (2) |
As a continuation of our studies relating to the synthesis of host compounds containing 5-mercapto-2,3-dihydro-1,3,4-thiadizol-2-ones (Cho, Park, Kim et al., 1999; Cho, Park, Hwang et al., 1999; Cho et al., 2000), we have prepared macrocycle (I) composed of two 5-mercapto-2,3-dihydro-1,3,4-thiadizol-2-ones and m-xylene. The determination of the structure of (I) is part of our interest in dealing with the macrocycles and this compound might be a potential host molecule for a palladium metal ion. Thus, we are in the progress of examining the role of this compound as an artificial receptor.
There are two molecules of (I) in the asymmetric unit. The S–C distances in the two molecules range from 1.720 (5) to 1.815 (5) Å, with a mean value of 1.766 (1) Å. The distances O25—C7 1.216 (5), O26—C21 1.207 (5), O52—C34 = 1.218 (5) and O53—C48 = 1.203 (5) Å clearly show double-bond character. These values are comparable with those found in 4,17,25,26-tetraaza-6,9,12,15-tetraoxa-2,19,21,24-tetrathiatricyclo- [18.4.11,4.117,20]hexacosa-1(25),20 (26)-diene-3,5,16,18-tetraone (Cho et al., 2000). The C—S—C angles in the five-membered rings range from 88.7 (2) to 89.9 (2)°, with a mean value of 89.1 (1)°, which is similiar to the value of 90.7 (1)° found in 2,3-dihydro-3-methyl-2-nitrimino-1,3-thiazole (Kyziol et al., 2000). All the five-membered rings are planar within 0.012 (3) Å, the two benzene rings are planar within 0.016 (3) Å and the two ethyl ether linkages are planar within 0.107 (3) Å. In the first molecule (Fig. 1), the dihedral angle between the five-membered rings N6/C7/S8/C9/N24 and C19/S20/C21/N22/N23 is 30.4 (2)°, with distances N6···N22 = 4.640 (5) Å, N23···N24 = 5.080 (5) Å, S10···S18 = 5.197 (2) Å and S8···S20 = 3.957 (2) Å, so that the two rings become narrower inwardly. The dihedral angle between benzene ring C12/C13/C14/C15/C16/C27 and ethyl ether linkage C1/C2/O3/C4/C5 is 37.35 (19)°, and they also become narrower inwardly, with a C4···C14 distance 4.125 (8) Å. In the second molecule (Fig. 1), the dihedral angle between the five-membered rings N33/C34/C35/C36/N51 and C46/S47/C48/N49/N50 is 30.5 (1)°, with distances N33···N49 = 4.561 (6) Å, N50···N51 = 5.015 (5) Å, S37···S45 = 5.111 (2) Å and S35···S47 = 3.812 (2) Å, and the dihedral angle between benzene ring C39/C40/C41/C42/C43/C54 and ethyl ether linkage C28/C29/O30/C31/C32 is 36.9 (2)°, becoming narrower inwardly with a C29···C41 distance of 4.125 (8) Å. Therefore, both molecules have a cage-like form with similiar conformations and each molecule appears to have sufficient space inside to introduce a guest atom into the molecule. The closest intermolecular distance is O26···H32A(1 - x, 0.5 + y, 0.5 - z) of 2.403 Å.