Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023055/na6258sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023055/na6258Isup2.hkl |
CCDC reference: 226995
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.045
- wR factor = 0.114
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.90 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C9 = 5.62 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C5 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: R-AXIS Software (Rigaku, 1997); cell refinement: R-AXIS Software; data reduction: R-AXIS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: WinGX (Farrugia, 1999).
C12H20N4OS2 | F(000) = 640 |
Mr = 300.44 | Dx = 1.221 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2y bc | Cell parameters from 20 reflections |
a = 12.315 (3) Å | θ = 2–11° |
b = 12.057 (2) Å | µ = 0.32 mm−1 |
c = 12.532 (3) Å | T = 293 K |
β = 118.55 (3)° | Pillar, colorless |
V = 1634.5 (8) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 4 |
Oxford Instruments point-detector diffractometer | Rint = 0.025 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 1.9° |
Graphite monochromator | h = −15→0 |
ω/2θ scans | k = −15→15 |
5132 measured reflections | l = −13→16 |
3130 independent reflections | 3 standard reflections every 100 reflections |
2189 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0601P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3130 reflections | Δρmax = 0.24 e Å−3 |
173 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0164 (16) |
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 | ||
S1 | 0.19508 (6) | 0.30704 (5) | 0.15133 (5) | 0.0499 (2) | |
S2 | 0.28853 (8) | 0.24256 (6) | 0.41476 (6) | 0.0664 (3) | |
O1 | 0.19319 (17) | 0.55544 (15) | 0.06702 (15) | 0.0615 (5) | |
N1 | 0.2103 (2) | 0.10543 (15) | 0.2283 (2) | 0.0550 (5) | |
N2 | 0.09057 (19) | 0.58687 (15) | 0.25521 (18) | 0.0474 (5) | |
N3 | 0.1408 (2) | 0.60743 (19) | 0.3759 (2) | 0.0716 (7) | |
N4 | 0.0813 (3) | 0.7659 (2) | 0.2684 (3) | 0.0811 (8) | |
C1 | 0.2368 (3) | 0.0129 (2) | 0.3117 (3) | 0.0891 (10) | |
H1A | 0.2701 | 0.0405 | 0.3932 | 0.134* | |
H1B | 0.2959 | −0.0356 | 0.3064 | 0.134* | |
H1C | 0.1620 | −0.0272 | 0.2907 | 0.134* | |
C2 | 0.1589 (3) | 0.0774 (2) | 0.0999 (3) | 0.0808 (9) | |
H2A | 0.1459 | 0.1441 | 0.0533 | 0.121* | |
H2B | 0.0816 | 0.0397 | 0.0729 | 0.121* | |
H2C | 0.2156 | 0.0300 | 0.0890 | 0.121* | |
C3 | 0.2316 (2) | 0.20907 (18) | 0.2702 (2) | 0.0418 (6) | |
C4 | 0.2115 (2) | 0.43895 (17) | 0.22616 (19) | 0.0404 (5) | |
H4B | 0.2699 | 0.4319 | 0.3130 | 0.049* | |
C5 | 0.2633 (2) | 0.51837 (18) | 0.1657 (2) | 0.0448 (6) | |
C6 | 0.3985 (3) | 0.5502 (2) | 0.2333 (3) | 0.0687 (8) | |
C7 | 0.4794 (3) | 0.4465 (3) | 0.2816 (4) | 0.1170 (14) | |
H7A | 0.4701 | 0.4015 | 0.2147 | 0.175* | |
H7B | 0.4544 | 0.4049 | 0.3316 | 0.175* | |
H7C | 0.5643 | 0.4680 | 0.3290 | 0.175* | |
C8 | 0.4335 (3) | 0.6142 (3) | 0.1503 (4) | 0.1227 (15) | |
H8A | 0.3832 | 0.6796 | 0.1213 | 0.184* | |
H8B | 0.4206 | 0.5685 | 0.0826 | 0.184* | |
H8C | 0.5190 | 0.6350 | 0.1943 | 0.184* | |
C9 | 0.4128 (3) | 0.6235 (3) | 0.3377 (4) | 0.1276 (16) | |
H9A | 0.3621 | 0.6884 | 0.3059 | 0.191* | |
H9B | 0.4977 | 0.6452 | 0.3848 | 0.191* | |
H9C | 0.3876 | 0.5832 | 0.3883 | 0.191* | |
C10 | 0.0855 (2) | 0.47617 (18) | 0.2084 (2) | 0.0479 (6) | |
H10A | 0.0262 | 0.4749 | 0.1225 | 0.058* | |
H10B | 0.0575 | 0.4247 | 0.2497 | 0.058* | |
C11 | 0.0566 (3) | 0.6814 (2) | 0.1953 (3) | 0.0670 (8) | |
H11A | 0.0194 | 0.6873 | 0.1112 | 0.080* | |
C12 | 0.1319 (3) | 0.7169 (3) | 0.3768 (3) | 0.0814 (10) | |
H12A | 0.1591 | 0.7568 | 0.4485 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0706 (5) | 0.0394 (3) | 0.0392 (3) | −0.0002 (3) | 0.0258 (3) | −0.0043 (3) |
S2 | 0.0912 (6) | 0.0635 (5) | 0.0442 (4) | 0.0060 (4) | 0.0321 (4) | 0.0057 (3) |
O1 | 0.0556 (12) | 0.0675 (12) | 0.0558 (11) | −0.0043 (9) | 0.0221 (10) | 0.0175 (9) |
N1 | 0.0601 (14) | 0.0384 (11) | 0.0736 (14) | −0.0054 (10) | 0.0376 (12) | −0.0031 (10) |
N2 | 0.0510 (13) | 0.0361 (10) | 0.0586 (12) | −0.0027 (9) | 0.0290 (11) | −0.0054 (9) |
N3 | 0.099 (2) | 0.0564 (14) | 0.0670 (15) | −0.0011 (13) | 0.0453 (15) | −0.0133 (12) |
N4 | 0.0787 (19) | 0.0432 (13) | 0.118 (2) | 0.0056 (12) | 0.0440 (18) | −0.0150 (15) |
C1 | 0.117 (3) | 0.0454 (15) | 0.129 (3) | 0.0008 (17) | 0.079 (3) | 0.0144 (18) |
C2 | 0.091 (2) | 0.0516 (16) | 0.095 (2) | −0.0153 (16) | 0.041 (2) | −0.0310 (16) |
C3 | 0.0378 (14) | 0.0420 (13) | 0.0506 (13) | −0.0003 (10) | 0.0251 (12) | 0.0011 (10) |
C4 | 0.0465 (14) | 0.0343 (11) | 0.0376 (11) | −0.0030 (10) | 0.0179 (11) | −0.0026 (9) |
C5 | 0.0438 (16) | 0.0392 (12) | 0.0495 (13) | −0.0008 (11) | 0.0209 (12) | −0.0014 (11) |
C6 | 0.0448 (17) | 0.096 (2) | 0.112 (2) | −0.0033 (13) | 0.0284 (16) | 0.0133 (17) |
C7 | 0.046 (2) | 0.126 (3) | 0.159 (4) | 0.014 (2) | 0.033 (2) | 0.036 (3) |
C8 | 0.070 (3) | 0.147 (4) | 0.151 (4) | −0.034 (2) | 0.053 (3) | 0.031 (3) |
C9 | 0.079 (3) | 0.143 (4) | 0.130 (3) | −0.058 (3) | 0.024 (3) | −0.062 (3) |
C10 | 0.0525 (16) | 0.0369 (12) | 0.0598 (14) | −0.0100 (11) | 0.0311 (13) | −0.0085 (10) |
C11 | 0.0645 (19) | 0.0465 (16) | 0.082 (2) | 0.0096 (14) | 0.0281 (16) | 0.0056 (14) |
C12 | 0.090 (3) | 0.064 (2) | 0.094 (2) | −0.0022 (17) | 0.047 (2) | −0.0326 (18) |
S1—C3 | 1.780 (2) | C4—C5 | 1.535 (3) |
S1—C4 | 1.810 (2) | C4—H4B | 0.9800 |
S2—C3 | 1.651 (2) | C5—C6 | 1.514 (4) |
O1—C5 | 1.205 (3) | C6—C8 | 1.513 (4) |
N1—C3 | 1.333 (3) | C6—C9 | 1.519 (4) |
N1—C1 | 1.453 (3) | C6—C7 | 1.530 (4) |
N1—C2 | 1.461 (4) | C7—H7A | 0.9600 |
N2—C11 | 1.317 (3) | C7—H7B | 0.9600 |
N2—N3 | 1.357 (3) | C7—H7C | 0.9600 |
N2—C10 | 1.448 (3) | C8—H8A | 0.9600 |
N3—C12 | 1.324 (4) | C8—H8B | 0.9600 |
N4—C11 | 1.306 (3) | C8—H8C | 0.9600 |
N4—C12 | 1.331 (4) | C9—H9A | 0.9600 |
C1—H1A | 0.9600 | C9—H9B | 0.9600 |
C1—H1B | 0.9600 | C9—H9C | 0.9600 |
C1—H1C | 0.9600 | C10—H10A | 0.9700 |
C2—H2A | 0.9600 | C10—H10B | 0.9700 |
C2—H2B | 0.9600 | C11—H11A | 0.9300 |
C2—H2C | 0.9600 | C12—H12A | 0.9300 |
C4—C10 | 1.525 (3) | ||
C3—S1—C4 | 103.16 (10) | C5—C6—C9 | 105.9 (2) |
C3—N1—C1 | 120.1 (2) | C8—C6—C7 | 110.0 (3) |
C3—N1—C2 | 123.6 (2) | C5—C6—C7 | 110.3 (2) |
C1—N1—C2 | 116.4 (2) | C9—C6—C7 | 110.5 (3) |
C11—N2—N3 | 109.1 (2) | C6—C7—H7A | 109.5 |
C11—N2—C10 | 128.7 (2) | C6—C7—H7B | 109.5 |
N3—N2—C10 | 122.1 (2) | H7A—C7—H7B | 109.5 |
C12—N3—N2 | 101.4 (2) | C6—C7—H7C | 109.5 |
C11—N4—C12 | 102.1 (2) | H7A—C7—H7C | 109.5 |
N1—C1—H1A | 109.5 | H7B—C7—H7C | 109.5 |
N1—C1—H1B | 109.5 | C6—C8—H8A | 109.5 |
H1A—C1—H1B | 109.5 | C6—C8—H8B | 109.5 |
N1—C1—H1C | 109.5 | H8A—C8—H8B | 109.5 |
H1A—C1—H1C | 109.5 | C6—C8—H8C | 109.5 |
H1B—C1—H1C | 109.5 | H8A—C8—H8C | 109.5 |
N1—C2—H2A | 109.5 | H8B—C8—H8C | 109.5 |
N1—C2—H2B | 109.5 | C6—C9—H9A | 109.5 |
H2A—C2—H2B | 109.5 | C6—C9—H9B | 109.5 |
N1—C2—H2C | 109.5 | H9A—C9—H9B | 109.5 |
H2A—C2—H2C | 109.5 | C6—C9—H9C | 109.5 |
H2B—C2—H2C | 109.5 | H9A—C9—H9C | 109.5 |
N1—C3—S2 | 124.36 (18) | H9B—C9—H9C | 109.5 |
N1—C3—S1 | 111.57 (17) | N2—C10—C4 | 111.56 (18) |
S2—C3—S1 | 124.05 (13) | N2—C10—H10A | 109.3 |
C10—C4—C5 | 112.26 (18) | C4—C10—H10A | 109.3 |
C10—C4—S1 | 109.17 (15) | N2—C10—H10B | 109.3 |
C5—C4—S1 | 105.23 (14) | C4—C10—H10B | 109.3 |
C10—C4—H4B | 110.0 | H10A—C10—H10B | 108.0 |
C5—C4—H4B | 110.0 | N4—C11—N2 | 111.8 (3) |
S1—C4—H4B | 110.0 | N4—C11—H11A | 124.1 |
O1—C5—C6 | 122.5 (2) | N2—C11—H11A | 124.1 |
O1—C5—C4 | 118.2 (2) | N3—C12—N4 | 115.6 (3) |
C6—C5—C4 | 119.2 (2) | N3—C12—H12A | 122.2 |
C8—C6—C5 | 110.1 (3) | N4—C12—H12A | 122.2 |
C8—C6—C9 | 110.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···S2 | 0.96 | 2.45 | 2.995 (3) | 116 |
C2—H2A···S1 | 0.96 | 2.24 | 2.831 (3) | 119 |
C4—H4B···S2 | 0.98 | 2.57 | 3.154 (2) | 118 |
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