Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017223/ob2015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017223/ob2015Isup2.hkl |
CCDC reference: 610858
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.069
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 2442 Count of symmetry unique reflns 1435 Completeness (_total/calc) 170.17% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1007 Fraction of Friedel pairs measured 0.702 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C9H12N2OS2 | F(000) = 480.00 |
Mr = 228.33 | Dx = 1.420 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 10137 reflections |
a = 6.314 (3) Å | θ = 3.1–27.5° |
b = 9.785 (3) Å | µ = 0.47 mm−1 |
c = 17.289 (6) Å | T = 298 K |
V = 1068.2 (7) Å3 | Chunk, colorless |
Z = 4 | 0.34 × 0.32 × 0.26 mm |
Rigaku R-AXIS RAPID diffractometer | 2239 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.022 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −8→8 |
Tmin = 0.859, Tmax = 0.886 | k = −12→12 |
10534 measured reflections | l = −22→22 |
2442 independent reflections |
Refinement on F2 | (Δ/σ)max < 0.001 |
R[F2 > 2σ(F2)] = 0.025 | Δρmax = 0.31 e Å−3 |
wR(F2) = 0.069 | Δρmin = −0.26 e Å−3 |
S = 1.04 | Extinction correction: Larson (1970) |
2442 reflections | Extinction coefficient: 45 (5) |
129 parameters | Absolute structure: Flack (1983), 1008 Friedel pairs |
H-atom parameters constrained | Absolute structure parameter: 0.006 (7) |
w = 1/[0.0004Fo2 + 1σ(Fo2)]/(4Fo2) |
Refinement. Refinement using all reflections. 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 | ||
S1 | 0.04353 (6) | 0.60974 (4) | 0.20201 (2) | 0.03931 (9) | |
S2 | 0.17570 (6) | 0.89377 (5) | 0.09627 (3) | 0.04656 (11) | |
O1 | −0.0031 (2) | 0.22126 (11) | 0.04547 (6) | 0.0516 (3) | |
N1 | 0.1586 (2) | 0.42420 (12) | 0.03804 (8) | 0.0433 (3) | |
N2 | −0.3508 (2) | 0.32026 (17) | 0.12712 (10) | 0.0599 (5) | |
C1 | 0.2521 (2) | 0.61538 (16) | 0.12898 (9) | 0.0371 (3) | |
C2 | 0.1774 (3) | 0.57177 (16) | 0.04817 (9) | 0.0409 (4) | |
C3 | 0.0011 (2) | 0.34424 (14) | 0.06290 (9) | 0.0384 (4) | |
C4 | −0.1661 (2) | 0.40696 (16) | 0.11468 (9) | 0.0393 (3) | |
C5 | −0.0670 (3) | 0.44160 (17) | 0.19316 (9) | 0.0439 (4) | |
C6 | 0.3292 (2) | 0.76025 (14) | 0.13013 (9) | 0.0370 (3) | |
C7 | 0.5146 (3) | 0.80840 (19) | 0.15989 (11) | 0.0508 (5) | |
C8 | 0.5304 (3) | 0.9526 (2) | 0.15511 (12) | 0.0587 (5) | |
C9 | 0.3609 (3) | 1.01199 (18) | 0.12234 (11) | 0.0507 (5) | |
H1 | 0.3679 | 0.5552 | 0.1452 | 0.045* | |
H4 | −0.2141 | 0.4923 | 0.0908 | 0.047* | |
H7 | 0.6192 | 0.7528 | 0.1810 | 0.061* | |
H8 | 0.6469 | 1.0014 | 0.1729 | 0.070* | |
H9 | 0.3464 | 1.1056 | 0.1148 | 0.061* | |
H21 | 0.0397 | 0.6125 | 0.0388 | 0.049* | |
H22 | 0.2781 | 0.6060 | 0.0105 | 0.049* | |
H51 | −0.1761 | 0.4319 | 0.2323 | 0.053* | |
H52 | 0.0452 | 0.3762 | 0.2029 | 0.053* | |
H101 | 0.2597 | 0.3844 | 0.0134 | 0.052* | |
H201 | −0.3976 | 0.2934 | 0.0829 | 0.072* | |
H202 | −0.2858 | 0.2474 | 0.1438 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0512 (2) | 0.03343 (18) | 0.03329 (18) | −0.00322 (19) | 0.00151 (17) | −0.00658 (16) |
S2 | 0.0472 (2) | 0.0392 (2) | 0.0534 (2) | −0.0026 (2) | −0.0086 (2) | 0.0038 (2) |
O1 | 0.0605 (8) | 0.0345 (5) | 0.0599 (7) | −0.0002 (5) | −0.0073 (6) | −0.0151 (5) |
N1 | 0.0463 (7) | 0.0381 (7) | 0.0456 (7) | 0.0005 (6) | 0.0090 (6) | −0.0152 (5) |
N2 | 0.0593 (10) | 0.0604 (9) | 0.0599 (10) | −0.0217 (8) | 0.0038 (8) | −0.0111 (8) |
C1 | 0.0353 (7) | 0.0330 (6) | 0.0430 (8) | 0.0026 (6) | −0.0013 (6) | −0.0044 (7) |
C2 | 0.0496 (9) | 0.0372 (7) | 0.0359 (8) | −0.0052 (7) | 0.0076 (7) | −0.0060 (6) |
C3 | 0.0451 (9) | 0.0348 (7) | 0.0352 (7) | 0.0021 (6) | −0.0107 (6) | −0.0064 (5) |
C4 | 0.0442 (8) | 0.0369 (7) | 0.0368 (7) | −0.0042 (7) | −0.0008 (6) | −0.0033 (6) |
C5 | 0.0605 (10) | 0.0374 (7) | 0.0338 (8) | −0.0088 (7) | 0.0009 (8) | 0.0001 (6) |
C6 | 0.0369 (8) | 0.0356 (7) | 0.0387 (8) | 0.0000 (6) | −0.0006 (7) | −0.0026 (6) |
C7 | 0.0445 (10) | 0.0475 (9) | 0.0603 (11) | −0.0048 (8) | −0.0072 (8) | −0.0006 (8) |
C8 | 0.0525 (11) | 0.0542 (10) | 0.0693 (12) | −0.0181 (9) | −0.0073 (10) | −0.0054 (9) |
C9 | 0.0599 (12) | 0.0382 (8) | 0.0540 (10) | −0.0131 (8) | 0.0034 (9) | 0.0018 (8) |
S1—C1 | 1.8254 (15) | C8—C9 | 1.343 (3) |
S1—C5 | 1.7938 (17) | N1—H101 | 0.860 |
S2—C6 | 1.7291 (16) | N2—H201 | 0.861 |
S2—C9 | 1.705 (2) | N2—H202 | 0.872 |
O1—C3 | 1.2408 (18) | C1—H1 | 0.980 |
N1—C2 | 1.459 (2) | C2—H21 | 0.970 |
N1—C3 | 1.336 (2) | C2—H22 | 0.970 |
N2—C4 | 1.458 (2) | C4—H4 | 0.980 |
C1—C2 | 1.535 (2) | C5—H51 | 0.970 |
C1—C6 | 1.499 (2) | C5—H52 | 0.970 |
C3—C4 | 1.514 (2) | C7—H7 | 0.930 |
C4—C5 | 1.532 (2) | C8—H8 | 0.930 |
C6—C7 | 1.363 (2) | C9—H9 | 0.930 |
C7—C8 | 1.417 (2) | ||
S2···O1i | 3.5092 (12) | H8···H1xiii | 3.189 |
O1···S2ii | 3.5092 (12) | H8···H22vii | 3.442 |
O1···O1iii | 3.5716 (19) | H8···H51xi | 3.462 |
O1···O1iv | 3.5716 (19) | H8···H52xiii | 3.144 |
O1···N1iii | 2.9450 (19) | H8···H101vii | 3.484 |
O1···N2iv | 3.161 (2) | H8···H201viii | 3.266 |
O1···C9ii | 3.353 (2) | H8···H202viii | 2.496 |
N1···O1iv | 2.9450 (19) | H9···O1i | 2.755 |
N1···C9v | 3.408 (2) | H9···O1vii | 3.384 |
N2···O1iii | 3.161 (2) | H9···N1i | 3.589 |
N2···C9vi | 3.524 (2) | H9···N1vii | 3.310 |
C9···O1i | 3.353 (2) | H9···N2viii | 2.848 |
C9···N1vii | 3.408 (2) | H9···C3i | 3.318 |
C9···N2viii | 3.524 (2) | H9···C3vii | 3.262 |
S1···H7ix | 3.045 | H9···H51xi | 3.321 |
S1···H8x | 3.101 | H9···H52i | 3.597 |
S1···H51xi | 3.454 | H9···H101i | 3.289 |
S1···H52xi | 3.132 | H9···H101vii | 3.426 |
S1···H202xi | 3.356 | H9···H201viii | 2.509 |
S2···H4vii | 3.490 | H9···H202viii | 2.751 |
S2···H21vii | 3.277 | H21···S2v | 3.277 |
S2···H22v | 3.116 | H21···C6v | 3.441 |
S2···H51xi | 2.987 | H21···C7v | 3.524 |
O1···H9ii | 2.755 | H21···C8v | 3.412 |
O1···H9v | 3.384 | H21···C9v | 3.243 |
O1···H101iii | 2.086 | H21···H22v | 3.323 |
O1···H201iv | 2.321 | H22···S2vii | 3.116 |
O1···H202iv | 3.562 | H22···C7v | 3.485 |
N1···H9ii | 3.589 | H22···C8v | 3.312 |
N1···H9v | 3.310 | H22···H8v | 3.442 |
N1···H201xii | 3.177 | H22···H21vii | 3.323 |
N1···H201iv | 3.005 | H51···S1xiv | 3.454 |
N1···H202iv | 3.582 | H51···S2xiv | 2.987 |
N2···H1ix | 2.921 | H51···C6xiv | 3.068 |
N2···H8vi | 3.219 | H51···C7xiv | 3.083 |
N2···H9vi | 2.848 | H51···C8xiv | 2.972 |
N2···H101ix | 3.210 | H51···C9xiv | 2.880 |
N2···H101iii | 3.226 | H51···H1ix | 3.466 |
C3···H9ii | 3.318 | H51···H7ix | 3.509 |
C3···H9v | 3.262 | H51···H8xiv | 3.462 |
C3···H101iii | 3.012 | H51···H9xiv | 3.321 |
C3···H201iv | 2.928 | H52···S1xiv | 3.132 |
C4···H1ix | 3.322 | H52···H7x | 3.159 |
C5···H8x | 3.569 | H52···H8x | 3.144 |
C6···H21vii | 3.441 | H52···H9ii | 3.597 |
C6···H51xi | 3.068 | H101···O1iv | 2.086 |
C7···H21vii | 3.524 | H101···N2xii | 3.210 |
C7···H22vii | 3.485 | H101···N2iv | 3.226 |
C7···H51xi | 3.083 | H101···C3iv | 3.012 |
C8···H21vii | 3.412 | H101···C9v | 3.589 |
C8···H22vii | 3.312 | H101···H8v | 3.484 |
C8···H51xi | 2.972 | H101···H9ii | 3.289 |
C8···H201viii | 3.590 | H101···H9v | 3.426 |
C8···H202viii | 3.116 | H101···H201xii | 2.630 |
C9···H21vii | 3.243 | H101···H201iv | 2.606 |
C9···H51xi | 2.880 | H101···H202iv | 3.023 |
C9···H101vii | 3.589 | H201···O1iii | 2.321 |
C9···H201viii | 3.221 | H201···N1ix | 3.177 |
C9···H202viii | 3.228 | H201···N1iii | 3.005 |
H1···N2xii | 2.921 | H201···C3iii | 2.928 |
H1···C4xii | 3.322 | H201···C8vi | 3.590 |
H1···H4xii | 2.869 | H201···C9vi | 3.221 |
H1···H8x | 3.189 | H201···H1ix | 3.148 |
H1···H51xii | 3.466 | H201···H8vi | 3.266 |
H1···H201xii | 3.148 | H201···H9vi | 2.509 |
H4···S2v | 3.490 | H201···H101ix | 2.630 |
H4···H1ix | 2.869 | H201···H101iii | 2.606 |
H4···H7ix | 3.168 | H202···S1xiv | 3.356 |
H7···S1xii | 3.045 | H202···O1iii | 3.562 |
H7···H4xii | 3.168 | H202···N1iii | 3.582 |
H7···H51xii | 3.509 | H202···C8vi | 3.116 |
H7···H52xiii | 3.159 | H202···C9vi | 3.228 |
H8···S1xiii | 3.101 | H202···H8vi | 2.496 |
H8···N2viii | 3.219 | H202···H9vi | 2.751 |
H8···C5xiii | 3.569 | H202···H101iii | 3.023 |
C1—S1—C5 | 104.45 (7) | H201—N2—H202 | 101.9 |
C6—S2—C9 | 92.21 (8) | S1—C1—H1 | 108.8 |
C2—N1—C3 | 126.95 (14) | C2—C1—H1 | 108.8 |
S1—C1—C2 | 113.54 (11) | C6—C1—H1 | 108.8 |
S1—C1—C6 | 104.71 (10) | N1—C2—H21 | 108.3 |
C2—C1—C6 | 112.01 (12) | N1—C2—H22 | 108.3 |
N1—C2—C1 | 114.15 (12) | C1—C2—H21 | 108.3 |
O1—C3—N1 | 120.37 (15) | C1—C2—H22 | 108.3 |
O1—C3—C4 | 121.45 (14) | H21—C2—H22 | 109.5 |
N1—C3—C4 | 118.15 (13) | N2—C4—H4 | 108.1 |
N2—C4—C3 | 114.15 (13) | C3—C4—H4 | 108.1 |
N2—C4—C5 | 108.95 (13) | C5—C4—H4 | 108.1 |
C3—C4—C5 | 109.17 (14) | S1—C5—H51 | 107.8 |
S1—C5—C4 | 115.94 (11) | S1—C5—H52 | 107.8 |
S2—C6—C1 | 121.86 (12) | C4—C5—H51 | 107.8 |
S2—C6—C7 | 110.38 (12) | C4—C5—H52 | 107.8 |
C1—C6—C7 | 127.67 (15) | H51—C5—H52 | 109.5 |
C6—C7—C8 | 112.50 (17) | C6—C7—H7 | 123.8 |
C7—C8—C9 | 113.55 (19) | C8—C7—H7 | 123.8 |
S2—C9—C8 | 111.36 (14) | C7—C8—H8 | 123.2 |
C2—N1—H101 | 116.5 | C9—C8—H8 | 123.2 |
C3—N1—H101 | 116.5 | S2—C9—H9 | 124.3 |
C4—N2—H201 | 108.7 | C8—C9—H9 | 124.3 |
C4—N2—H202 | 98.5 | ||
C1—S1—C5—C4 | −61.14 (14) | C2—C1—C6—C7 | −130.31 (18) |
C5—S1—C1—C2 | 51.57 (12) | C6—C1—C2—N1 | 163.30 (14) |
C5—S1—C1—C6 | 174.04 (10) | O1—C3—C4—N2 | −12.8 (2) |
C6—S2—C9—C8 | −0.03 (12) | O1—C3—C4—C5 | 109.35 (17) |
C9—S2—C6—C1 | 176.74 (14) | N1—C3—C4—N2 | 169.19 (14) |
C9—S2—C6—C7 | −0.03 (11) | N1—C3—C4—C5 | −68.62 (18) |
C2—N1—C3—O1 | 174.70 (15) | N2—C4—C5—S1 | −144.26 (12) |
C2—N1—C3—C4 | −7.3 (2) | C3—C4—C5—S1 | 90.48 (14) |
C3—N1—C2—C1 | 78.4 (2) | S2—C6—C7—C8 | 0.09 (16) |
S1—C1—C2—N1 | −78.35 (16) | C1—C6—C7—C8 | −176.45 (16) |
S1—C1—C6—S2 | −69.96 (13) | C6—C7—C8—C9 | −0.1 (2) |
S1—C1—C6—C7 | 106.22 (17) | C7—C8—C9—S2 | 0.1 (2) |
C2—C1—C6—S2 | 53.51 (18) |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) x−1/2, −y+1/2, −z; (iv) x+1/2, −y+1/2, −z; (v) x−1/2, −y+3/2, −z; (vi) x−1, y−1, z; (vii) x+1/2, −y+3/2, −z; (viii) x+1, y+1, z; (ix) x−1, y, z; (x) −x+1, y−1/2, −z+1/2; (xi) −x, y+1/2, −z+1/2; (xii) x+1, y, z; (xiii) −x+1, y+1/2, −z+1/2; (xiv) −x, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H101···O1iv | 0.86 | 2.09 | 2.945 (2) | 177 |
N2—H201···O1iii | 0.86 | 2.32 | 3.161 (2) | 165 |
N2—H202···O1 | 0.87 | 2.48 | 2.784 (2) | 101 |
Symmetry codes: (iii) x−1/2, −y+1/2, −z; (iv) x+1/2, −y+1/2, −z. |