Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011833/tk6165sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011833/tk6165Isup2.hkl |
CCDC reference: 242337
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.097
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.10 Ratio
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... S4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku and Rigaku/MSC, 2000–2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: CrystalStructure.
C20H24N6O4S4 | F(000) = 1128 |
Mr = 540.69 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 15829 reflections |
a = 13.342 (1) Å | θ = 1.3–27.4° |
b = 15.552 (1) Å | µ = 0.42 mm−1 |
c = 12.0130 (8) Å | T = 295 K |
β = 94.076 (2)° | Block, colorless |
V = 2486.4 (3) Å3 | 0.32 × 0.26 × 0.17 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 3436 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.039 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→17 |
Tmin = 0.809, Tmax = 0.931 | k = −20→20 |
23803 measured reflections | l = −15→15 |
5666 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[0.0013Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.097 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.31 e Å−3 |
3436 reflections | Δρmin = −0.22 e Å−3 |
331 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S(1) | 0.77703 (5) | 0.64831 (4) | 0.10365 (5) | 0.0449 (2) | |
S(2) | 0.67273 (6) | 0.89651 (5) | 0.24815 (7) | 0.0636 (2) | |
S(3) | 0.70588 (5) | 0.53095 (4) | 0.06410 (5) | 0.0436 (2) | |
S(4) | 0.81304 (7) | 0.24531 (6) | 0.06394 (9) | 0.0820 (3) | |
O(1) | 0.6995 (1) | 0.6332 (1) | 0.4533 (1) | 0.0550 (6) | |
O(2) | 0.8413 (1) | 0.8099 (1) | 0.2732 (2) | 0.0664 (7) | |
O(3) | 0.8154 (1) | 0.4224 (1) | 0.3873 (1) | 0.0541 (6) | |
O(4) | 0.6509 (1) | 0.3246 (1) | 0.1185 (2) | 0.0690 (7) | |
N(1) | 0.9793 (2) | 0.5713 (1) | 0.3374 (2) | 0.0483 (6) | |
N(2) | 0.9076 (1) | 0.6043 (1) | 0.3976 (2) | 0.0415 (6) | |
N(3) | 0.6993 (1) | 0.7465 (1) | 0.3372 (2) | 0.0392 (5) | |
N(4) | 0.5274 (2) | 0.5236 (1) | 0.3105 (2) | 0.0459 (6) | |
N(5) | 0.6033 (2) | 0.4699 (1) | 0.3473 (2) | 0.0428 (6) | |
N(6) | 0.8011 (1) | 0.3595 (1) | 0.2186 (2) | 0.0435 (6) | |
C(1) | 1.1116 (3) | 0.5451 (4) | 0.1624 (4) | 0.149 (2) | |
C(2) | 1.0047 (2) | 0.5496 (2) | 0.1381 (3) | 0.068 (1) | |
C(3) | 0.9457 (2) | 0.5809 (2) | 0.2314 (2) | 0.0440 (7) | |
C(4) | 0.8521 (2) | 0.6218 (1) | 0.2232 (2) | 0.0371 (6) | |
C(5) | 0.8299 (2) | 0.6365 (1) | 0.3325 (2) | 0.0362 (6) | |
C(6) | 0.9208 (2) | 0.6028 (2) | 0.5196 (2) | 0.0633 (9) | |
C(7) | 0.7401 (2) | 0.6707 (1) | 0.3814 (2) | 0.0377 (7) | |
C(8) | 0.6006 (2) | 0.7723 (2) | 0.3693 (2) | 0.0487 (8) | |
C(9) | 0.5640 (2) | 0.8409 (2) | 0.2888 (3) | 0.069 (1) | |
C(10) | 0.7533 (2) | 0.8106 (2) | 0.2868 (2) | 0.0465 (8) | |
C(11) | 0.3894 (2) | 0.6372 (2) | 0.1915 (3) | 0.071 (1) | |
C(12) | 0.4863 (2) | 0.6129 (2) | 0.1429 (2) | 0.0562 (8) | |
C(13) | 0.5507 (2) | 0.5508 (2) | 0.2109 (2) | 0.0400 (7) | |
C(14) | 0.6414 (2) | 0.5139 (1) | 0.1827 (2) | 0.0371 (6) | |
C(15) | 0.6724 (2) | 0.4622 (1) | 0.2729 (2) | 0.0370 (6) | |
C(16) | 0.5998 (3) | 0.4301 (2) | 0.4563 (2) | 0.066 (1) | |
C(17) | 0.7664 (2) | 0.4132 (1) | 0.2989 (2) | 0.0389 (7) | |
C(18) | 0.9024 (2) | 0.3241 (2) | 0.2385 (3) | 0.0570 (9) | |
C(19) | 0.9294 (2) | 0.2854 (2) | 0.1298 (3) | 0.072 (1) | |
C(20) | 0.7402 (2) | 0.3170 (2) | 0.1364 (2) | 0.0523 (8) | |
H(1) | 1.1406 | 0.5991 | 0.1432 | 0.180* | |
H(2) | 1.1400 | 0.4999 | 0.1203 | 0.180* | |
H(3) | 1.1256 | 0.5345 | 0.2407 | 0.180* | |
H(4) | 0.9909 | 0.5876 | 0.0749 | 0.083* | |
H(5) | 0.9818 | 0.4920 | 0.1184 | 0.083* | |
H(6) | 0.8929 | 0.5507 | 0.5468 | 0.076* | |
H(7) | 0.8873 | 0.6513 | 0.5495 | 0.075* | |
H(8) | 0.9912 | 0.6053 | 0.5424 | 0.075* | |
H(9) | 0.5555 | 0.7233 | 0.3656 | 0.059* | |
H(10) | 0.6059 | 0.7950 | 0.4447 | 0.059* | |
H(11) | 0.5198 | 0.8805 | 0.3240 | 0.083* | |
H(12) | 0.5282 | 0.8150 | 0.2241 | 0.083* | |
H(13) | 0.3373 | 0.5977 | 0.1663 | 0.085* | |
H(14) | 0.3704 | 0.6944 | 0.1689 | 0.085* | |
H(15) | 0.3991 | 0.6347 | 0.2714 | 0.085* | |
H(16) | 0.4696 | 0.5868 | 0.0706 | 0.067* | |
H(17) | 0.5249 | 0.6648 | 0.1334 | 0.067* | |
H(18) | 0.6333 | 0.4663 | 0.5120 | 0.080* | |
H(19) | 0.6331 | 0.3753 | 0.4557 | 0.080* | |
H(20) | 0.5312 | 0.4220 | 0.4732 | 0.080* | |
H(21) | 0.9490 | 0.3694 | 0.2626 | 0.068* | |
H(22) | 0.9029 | 0.2798 | 0.2954 | 0.068* | |
H(23) | 0.9775 | 0.2391 | 0.1421 | 0.087* | |
H(24) | 0.9572 | 0.3293 | 0.0836 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S(1) | 0.0481 (4) | 0.0518 (4) | 0.0343 (3) | −0.0017 (3) | 0.0001 (3) | 0.0091 (3) |
S(2) | 0.0660 (5) | 0.0458 (4) | 0.0805 (6) | 0.0148 (4) | 0.0160 (4) | 0.0134 (4) |
S(3) | 0.0470 (4) | 0.0540 (4) | 0.0301 (3) | 0.0004 (3) | 0.0044 (3) | −0.0033 (3) |
S(4) | 0.0775 (6) | 0.0754 (6) | 0.0927 (7) | 0.0158 (5) | 0.0034 (5) | −0.0418 (5) |
O(1) | 0.062 (1) | 0.059 (1) | 0.046 (1) | 0.0057 (9) | 0.0177 (9) | 0.0105 (9) |
O(2) | 0.047 (1) | 0.050 (1) | 0.105 (2) | 0.0002 (9) | 0.024 (1) | 0.012 (1) |
O(3) | 0.058 (1) | 0.061 (1) | 0.041 (1) | 0.009 (1) | −0.0073 (9) | −0.0001 (9) |
O(4) | 0.046 (1) | 0.070 (1) | 0.089 (2) | 0.000 (1) | −0.008 (1) | −0.027 (1) |
N(1) | 0.039 (1) | 0.054 (1) | 0.052 (1) | 0.010 (1) | 0.002 (1) | −0.003 (1) |
N(2) | 0.042 (1) | 0.047 (1) | 0.035 (1) | 0.0070 (9) | −0.0034 (9) | 0.0001 (9) |
N(3) | 0.033 (1) | 0.040 (1) | 0.046 (1) | 0.0044 (9) | 0.0073 (9) | 0.0015 (9) |
N(4) | 0.042 (1) | 0.047 (1) | 0.050 (1) | 0.006 (1) | 0.009 (1) | −0.001 (1) |
N(5) | 0.047 (1) | 0.044 (1) | 0.039 (1) | 0.004 (1) | 0.0095 (9) | 0.0039 (9) |
N(6) | 0.038 (1) | 0.046 (1) | 0.046 (1) | 0.0079 (9) | −0.0016 (9) | −0.007 (1) |
C(1) | 0.057 (2) | 0.277 (8) | 0.114 (4) | 0.033 (4) | 0.028 (2) | −0.063 (4) |
C(2) | 0.060 (2) | 0.082 (2) | 0.063 (2) | 0.011 (2) | 0.020 (2) | −0.006 (2) |
C(3) | 0.038 (1) | 0.050 (2) | 0.045 (1) | 0.002 (1) | 0.004 (1) | −0.003 (1) |
C(4) | 0.035 (1) | 0.042 (1) | 0.034 (1) | −0.001 (1) | 0.000 (1) | 0.003 (1) |
C(5) | 0.036 (1) | 0.037 (1) | 0.035 (1) | 0.001 (1) | 0.001 (1) | 0.002 (1) |
C(6) | 0.071 (2) | 0.080 (2) | 0.037 (1) | 0.019 (2) | −0.011 (1) | 0.000 (1) |
C(7) | 0.040 (1) | 0.039 (1) | 0.034 (1) | 0.001 (1) | 0.000 (1) | −0.001 (1) |
C(8) | 0.036 (1) | 0.051 (2) | 0.061 (2) | 0.003 (1) | 0.010 (1) | −0.005 (1) |
C(9) | 0.047 (2) | 0.061 (2) | 0.099 (3) | 0.014 (1) | 0.002 (2) | 0.008 (2) |
C(10) | 0.047 (2) | 0.040 (1) | 0.054 (2) | 0.002 (1) | 0.010 (1) | 0.001 (1) |
C(11) | 0.046 (2) | 0.068 (2) | 0.097 (3) | 0.013 (2) | 0.002 (2) | 0.008 (2) |
C(12) | 0.054 (2) | 0.058 (2) | 0.056 (2) | 0.012 (1) | −0.001 (1) | 0.002 (1) |
C(13) | 0.036 (1) | 0.042 (1) | 0.042 (1) | 0.001 (1) | 0.002 (1) | −0.002 (1) |
C(14) | 0.036 (1) | 0.042 (1) | 0.034 (1) | −0.002 (1) | 0.001 (1) | −0.002 (1) |
C(15) | 0.038 (1) | 0.038 (1) | 0.035 (1) | 0.000 (1) | 0.005 (1) | −0.002 (1) |
C(16) | 0.074 (2) | 0.077 (2) | 0.050 (2) | 0.012 (2) | 0.024 (2) | 0.018 (2) |
C(17) | 0.041 (1) | 0.038 (1) | 0.038 (1) | −0.000 (1) | 0.004 (1) | 0.003 (1) |
C(18) | 0.045 (2) | 0.062 (2) | 0.064 (2) | 0.018 (1) | 0.001 (1) | 0.003 (1) |
C(19) | 0.056 (2) | 0.081 (2) | 0.080 (2) | 0.024 (2) | 0.012 (2) | −0.012 (2) |
C(20) | 0.055 (2) | 0.045 (2) | 0.057 (2) | 0.003 (1) | 0.002 (1) | −0.010 (1) |
S(1)—S(3) | 2.0962 (9) | C(11)—C(12) | 1.504 (5) |
S(1)—C(4) | 1.741 (2) | C(12)—C(13) | 1.496 (4) |
S(2)—C(9) | 1.787 (3) | C(13)—C(14) | 1.402 (3) |
S(2)—C(10) | 1.756 (3) | C(14)—C(15) | 1.389 (3) |
S(3)—C(14) | 1.736 (2) | C(15)—C(17) | 1.482 (3) |
S(4)—C(19) | 1.803 (3) | C(18)—C(19) | 1.505 (5) |
S(4)—C(20) | 1.751 (3) | C(1)—H(1) | 0.9600 |
O(1)—C(7) | 1.203 (3) | C(1)—H(2) | 0.9600 |
O(2)—C(10) | 1.197 (3) | C(1)—H(3) | 0.9600 |
O(3)—C(17) | 1.214 (3) | C(2)—H(4) | 0.9700 |
O(4)—C(20) | 1.201 (4) | C(2)—H(5) | 0.9700 |
N(1)—N(2) | 1.341 (3) | C(6)—H(6) | 0.9600 |
N(1)—C(3) | 1.329 (3) | C(6)—H(7) | 0.9600 |
N(2)—C(5) | 1.350 (3) | C(6)—H(8) | 0.9600 |
N(2)—C(6) | 1.463 (3) | C(8)—H(9) | 0.9700 |
N(3)—C(7) | 1.388 (3) | C(8)—H(10) | 0.9700 |
N(3)—C(8) | 1.455 (3) | C(9)—H(11) | 0.9700 |
N(3)—C(10) | 1.394 (3) | C(9)—H(12) | 0.9700 |
N(4)—N(5) | 1.361 (3) | C(11)—H(13) | 0.9600 |
N(4)—C(13) | 1.327 (3) | C(11)—H(14) | 0.9600 |
N(5)—C(15) | 1.335 (3) | C(11)—H(15) | 0.9600 |
N(5)—C(16) | 1.452 (4) | C(12)—H(16) | 0.9700 |
N(6)—C(17) | 1.381 (3) | C(12)—H(17) | 0.9700 |
N(6)—C(18) | 1.464 (3) | C(16)—H(18) | 0.9600 |
N(6)—C(20) | 1.399 (3) | C(16)—H(19) | 0.9600 |
C(1)—C(2) | 1.437 (5) | C(16)—H(20) | 0.9600 |
C(2)—C(3) | 1.496 (4) | C(18)—H(21) | 0.9700 |
C(3)—C(4) | 1.399 (3) | C(18)—H(22) | 0.9700 |
C(4)—C(5) | 1.385 (3) | C(19)—H(23) | 0.9700 |
C(5)—C(7) | 1.471 (3) | C(19)—H(24) | 0.9700 |
C(8)—C(9) | 1.499 (4) | ||
C(4)—S(1)—S(3) | 101.83 (8) | S(2)—C(9)—H(11) | 109.9863 |
S(1)—S(3)—C(14) | 100.95 (8) | S(2)—C(9)—H(12) | 110.2471 |
S(1)—C(4)—C(3) | 128.6 (2) | S(4)—C(19)—H(23) | 110.4619 |
S(1)—C(4)—C(5) | 126.4 (2) | S(4)—C(19)—H(24) | 110.2139 |
C(10)—S(2)—C(9) | 93.1 (1) | N(2)—C(6)—H(6) | 109.4314 |
S(2)—C(9)—C(8) | 106.7 (2) | N(2)—C(6)—H(7) | 109.6376 |
S(2)—C(10)—O(2) | 124.0 (2) | N(2)—C(6)—H(8) | 109.3489 |
S(2)—C(10)—N(3) | 109.5 (2) | N(3)—C(8)—H(9) | 109.9495 |
S(3)—C(14)—C(13) | 128.5 (2) | N(3)—C(8)—H(10) | 109.9742 |
S(3)—C(14)—C(15) | 126.2 (2) | N(5)—C(16)—H(18) | 109.5131 |
C(20)—S(4)—C(19) | 93.0 (2) | N(5)—C(16)—H(19) | 109.1491 |
S(4)—C(19)—C(18) | 105.5 (2) | N(5)—C(16)—H(20) | 109.7462 |
S(4)—C(20)—O(4) | 123.5 (2) | N(6)—C(18)—H(21) | 109.9803 |
S(4)—C(20)—N(6) | 109.7 (2) | N(6)—C(18)—H(22) | 110.0135 |
O(1)—C(7)—N(3) | 120.2 (2) | C(1)—C(2)—H(4) | 108.6237 |
O(1)—C(7)—C(5) | 122.2 (2) | H(1)—C(1)—C(2) | 108.6333 |
O(2)—C(10)—N(3) | 126.5 (2) | H(3)—C(1)—C(2) | 109.1830 |
O(3)—C(17)—N(6) | 119.7 (2) | C(1)—C(2)—H(5) | 107.1952 |
O(3)—C(17)—C(15) | 121.3 (2) | H(2)—C(1)—C(2) | 110.5894 |
O(4)—C(20)—N(6) | 126.7 (3) | H(3)—C(1)—H(1) | 109.4617 |
C(3)—N(1)—N(2) | 105.6 (2) | H(2)—C(1)—H(1) | 109.4732 |
N(1)—N(2)—C(5) | 112.2 (2) | H(3)—C(1)—H(2) | 109.4802 |
N(1)—N(2)—C(6) | 119.6 (2) | H(4)—C(2)—C(3) | 107.8802 |
N(1)—C(3)—C(2) | 121.5 (2) | H(5)—C(2)—C(3) | 108.0228 |
N(1)—C(3)—C(4) | 110.9 (2) | H(5)—C(2)—H(4) | 109.4563 |
N(2)—C(5)—C(4) | 106.3 (2) | H(7)—C(6)—H(6) | 109.4709 |
N(2)—C(5)—C(7) | 121.0 (2) | H(8)—C(6)—H(6) | 109.4704 |
C(6)—N(2)—C(5) | 128.3 (2) | H(8)—C(6)—H(7) | 109.4681 |
N(3)—C(7)—C(5) | 117.5 (2) | H(9)—C(8)—C(9) | 110.9077 |
C(10)—N(3)—C(7) | 125.0 (2) | H(10)—C(8)—C(9) | 109.9564 |
C(8)—N(3)—C(7) | 118.1 (2) | C(8)—C(9)—H(11) | 110.5510 |
C(10)—N(3)—C(8) | 115.0 (2) | C(8)—C(9)—H(12) | 109.8932 |
N(3)—C(8)—C(9) | 106.6 (2) | H(10)—C(8)—H(9) | 109.4618 |
C(13)—N(4)—N(5) | 105.8 (2) | H(12)—C(9)—H(11) | 109.4608 |
N(4)—N(5)—C(15) | 111.8 (2) | C(11)—C(12)—H(17) | 108.3413 |
N(4)—N(5)—C(16) | 119.0 (2) | C(11)—C(12)—H(16) | 107.7252 |
N(4)—C(13)—C(14) | 110.4 (2) | H(13)—C(11)—C(12) | 109.8317 |
N(4)—C(13)—C(12) | 122.4 (2) | H(15)—C(11)—C(12) | 108.6618 |
N(5)—C(15)—C(14) | 106.8 (2) | H(14)—C(11)—C(12) | 109.9129 |
N(5)—C(15)—C(17) | 121.3 (2) | H(15)—C(11)—H(13) | 109.4726 |
C(16)—N(5)—C(15) | 129.3 (2) | H(14)—C(11)—H(13) | 109.4727 |
N(6)—C(17)—C(15) | 118.9 (2) | H(15)—C(11)—H(14) | 109.4726 |
C(20)—N(6)—C(17) | 124.9 (2) | H(17)—C(12)—C(13) | 108.1998 |
C(18)—N(6)—C(17) | 117.7 (2) | H(16)—C(12)—C(13) | 107.7678 |
C(20)—N(6)—C(18) | 114.9 (2) | H(17)—C(12)—H(16) | 109.4632 |
N(6)—C(18)—C(19) | 106.5 (2) | H(19)—C(16)—H(18) | 109.4736 |
C(1)—C(2)—C(3) | 115.6 (3) | H(20)—C(16)—H(18) | 109.4766 |
C(2)—C(3)—C(4) | 127.6 (2) | H(20)—C(16)—H(19) | 109.4680 |
C(3)—C(4)—C(5) | 105.0 (2) | H(21)—C(18)—C(19) | 111.1785 |
C(4)—C(5)—C(7) | 132.4 (2) | H(22)—C(18)—C(19) | 109.7024 |
C(11)—C(12)—C(13) | 115.3 (3) | C(18)—C(19)—H(23) | 111.2263 |
C(12)—C(13)—C(14) | 127.2 (2) | C(18)—C(19)—H(24) | 109.8968 |
C(13)—C(14)—C(15) | 105.2 (2) | H(22)—C(18)—H(21) | 109.4644 |
C(14)—C(15)—C(17) | 131.5 (2) | H(24)—C(19)—H(23) | 109.4605 |
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