Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004132/fl2003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004132/fl2003Isup2.hkl |
CCDC reference: 601164
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.109
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.754 0.920 Tmin(prime) and Tmax expected: 0.902 0.918 RR(prime) = 0.835 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1995) and PLATON (Spek, 2003).
C12H14N2O4S2 | F(000) = 656 |
Mr = 314.37 | Dx = 1.464 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5103 reflections |
a = 8.1322 (7) Å | θ = 2.2–28.3° |
b = 11.1027 (9) Å | µ = 0.39 mm−1 |
c = 16.0757 (14) Å | T = 173 K |
β = 100.680 (2)° | Block, colourless |
V = 1426.3 (2) Å3 | 0.26 × 0.22 × 0.22 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 3534 independent reflections |
Radiation source: fine-focus sealed tube | 3357 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003) | h = −10→10 |
Tmin = 0.754, Tmax = 0.92 | k = −14→14 |
15246 measured reflections | l = −21→21 |
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)] = 0.047 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.109 | All H-atom parameters refined |
S = 1.20 | w = 1/[σ2(Fo2) + (0.0424P)2 + 1.2568P] where P = (Fo2 + 2Fc2)/3 |
3534 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.1806 (0.0054) x - 6.1783 (0.0093) y + 3.0396 (0.0162) z = 4.0526 (0.0072) * 0.0058 (0.0012) N1 * -0.0047 (0.0012) C2 * 0.0018 (0.0012) C3 * 0.0018 (0.0013) C4 * -0.0047 (0.0012) C5 Rms deviation of fitted atoms = 0.0041 - 0.9721 (0.0071) x + 7.3615 (0.0076) y + 12.0299 (0.0098) z = 1.1592 (0.0038) Angle to previous plane (with approximate e.s.d.) = 77.78 (0.07) * -0.0027 (0.0014) C8 * 0.0102 (0.0014) C9 * -0.0082 (0.0015) C10 * -0.0015 (0.0016) C11 * 0.0091 (0.0017) C12 * -0.0069 (0.0016) C13 Rms deviation of fitted atoms = 0.0072 |
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 | 0.76003 (6) | 0.14377 (4) | 0.06525 (3) | 0.01749 (13) | |
S2 | 1.12146 (6) | 0.53927 (4) | 0.18637 (3) | 0.01793 (13) | |
O1 | 0.74294 (18) | 0.04472 (13) | 0.11930 (9) | 0.0236 (3) | |
O3 | 1.12617 (18) | 0.57871 (13) | 0.10194 (9) | 0.0242 (3) | |
O4 | 1.07297 (19) | 0.62177 (13) | 0.24590 (10) | 0.0267 (3) | |
N1 | 0.8467 (2) | 0.25417 (15) | 0.13011 (10) | 0.0180 (3) | |
O2 | 0.86055 (17) | 0.13591 (14) | 0.00161 (9) | 0.0242 (3) | |
N2 | 1.3090 (2) | 0.49114 (15) | 0.22630 (10) | 0.0203 (3) | |
C8 | 0.5610 (2) | 0.19798 (18) | 0.02032 (12) | 0.0181 (4) | |
C3 | 0.9852 (2) | 0.41716 (17) | 0.17857 (12) | 0.0174 (4) | |
C9 | 0.4222 (2) | 0.14403 (19) | 0.04319 (13) | 0.0215 (4) | |
C5 | 0.8208 (2) | 0.27053 (19) | 0.21248 (12) | 0.0213 (4) | |
C2 | 0.9465 (2) | 0.34516 (17) | 0.10874 (12) | 0.0180 (4) | |
C4 | 0.9060 (3) | 0.37005 (19) | 0.24382 (13) | 0.0215 (4) | |
C12 | 0.3880 (3) | 0.3310 (2) | −0.07406 (14) | 0.0309 (5) | |
C11 | 0.2481 (3) | 0.2764 (2) | −0.05285 (14) | 0.0285 (5) | |
C10 | 0.2645 (3) | 0.1832 (2) | 0.00492 (15) | 0.0260 (4) | |
C6 | 1.3342 (3) | 0.4506 (2) | 0.31501 (14) | 0.0301 (5) | |
C13 | 0.5469 (3) | 0.2912 (2) | −0.03821 (13) | 0.0254 (4) | |
C7 | 1.3836 (3) | 0.4085 (2) | 0.17229 (15) | 0.0275 (5) | |
H4 | 0.909 (3) | 0.401 (2) | 0.2954 (15) | 0.023 (6)* | |
H7B | 1.360 (3) | 0.435 (2) | 0.1139 (16) | 0.023 (6)* | |
H2 | 0.974 (3) | 0.351 (2) | 0.0543 (16) | 0.022 (6)* | |
H9 | 0.439 (3) | 0.086 (2) | 0.0823 (16) | 0.026 (6)* | |
H5 | 0.749 (3) | 0.216 (2) | 0.2350 (15) | 0.025 (6)* | |
H10 | 0.169 (3) | 0.148 (2) | 0.0193 (17) | 0.032 (7)* | |
H13 | 0.637 (4) | 0.324 (2) | −0.0526 (17) | 0.034 (7)* | |
H6B | 1.292 (3) | 0.511 (3) | 0.3475 (17) | 0.032 (7)* | |
H6A | 1.278 (4) | 0.373 (3) | 0.3226 (18) | 0.042 (8)* | |
H7C | 1.502 (4) | 0.407 (3) | 0.1948 (18) | 0.044 (8)* | |
H7A | 1.337 (3) | 0.326 (3) | 0.1725 (17) | 0.033 (7)* | |
H11 | 0.142 (4) | 0.302 (3) | −0.0781 (17) | 0.036 (7)* | |
H12 | 0.374 (4) | 0.398 (3) | −0.1135 (19) | 0.043 (8)* | |
H6C | 1.450 (4) | 0.442 (3) | 0.3323 (17) | 0.036 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0147 (2) | 0.0182 (2) | 0.0196 (2) | −0.00135 (16) | 0.00309 (16) | −0.00319 (17) |
S2 | 0.0193 (2) | 0.0140 (2) | 0.0201 (2) | −0.00067 (16) | 0.00272 (17) | 0.00041 (17) |
O1 | 0.0218 (7) | 0.0199 (7) | 0.0285 (8) | −0.0007 (6) | 0.0029 (6) | 0.0015 (6) |
O3 | 0.0243 (7) | 0.0230 (7) | 0.0251 (7) | −0.0003 (6) | 0.0038 (6) | 0.0069 (6) |
O4 | 0.0294 (8) | 0.0188 (7) | 0.0328 (8) | 0.0000 (6) | 0.0082 (6) | −0.0069 (6) |
N1 | 0.0185 (7) | 0.0196 (8) | 0.0156 (7) | −0.0030 (6) | 0.0025 (6) | −0.0020 (6) |
O2 | 0.0193 (7) | 0.0298 (8) | 0.0244 (7) | −0.0025 (6) | 0.0067 (6) | −0.0094 (6) |
N2 | 0.0185 (8) | 0.0199 (8) | 0.0211 (8) | −0.0008 (6) | −0.0002 (6) | −0.0012 (6) |
C8 | 0.0148 (8) | 0.0206 (9) | 0.0185 (9) | −0.0010 (7) | 0.0023 (7) | −0.0038 (7) |
C3 | 0.0169 (8) | 0.0173 (8) | 0.0178 (9) | −0.0006 (7) | 0.0027 (7) | 0.0008 (7) |
C9 | 0.0195 (9) | 0.0208 (9) | 0.0243 (10) | −0.0002 (7) | 0.0048 (7) | −0.0012 (8) |
C5 | 0.0220 (9) | 0.0249 (10) | 0.0179 (9) | −0.0026 (8) | 0.0062 (7) | −0.0004 (8) |
C2 | 0.0171 (8) | 0.0200 (9) | 0.0171 (9) | −0.0011 (7) | 0.0031 (7) | 0.0015 (7) |
C4 | 0.0255 (10) | 0.0237 (10) | 0.0163 (9) | −0.0026 (8) | 0.0062 (7) | −0.0032 (7) |
C12 | 0.0334 (12) | 0.0323 (12) | 0.0247 (11) | 0.0020 (9) | −0.0006 (9) | 0.0064 (9) |
C11 | 0.0211 (10) | 0.0349 (12) | 0.0268 (11) | 0.0066 (9) | −0.0026 (8) | −0.0053 (9) |
C10 | 0.0163 (9) | 0.0296 (11) | 0.0322 (11) | −0.0009 (8) | 0.0049 (8) | −0.0043 (9) |
C6 | 0.0274 (11) | 0.0394 (13) | 0.0204 (10) | −0.0004 (10) | −0.0039 (8) | 0.0017 (9) |
C13 | 0.0238 (10) | 0.0296 (11) | 0.0227 (10) | −0.0041 (8) | 0.0038 (8) | 0.0036 (8) |
C7 | 0.0262 (11) | 0.0261 (11) | 0.0305 (11) | 0.0073 (9) | 0.0061 (9) | 0.0009 (9) |
S1—O1 | 1.4243 (15) | C5—C4 | 1.351 (3) |
S1—O2 | 1.4255 (14) | C5—H5 | 0.96 (3) |
S1—N1 | 1.6775 (16) | C2—H2 | 0.94 (2) |
S1—C8 | 1.7524 (19) | C4—H4 | 0.90 (2) |
S2—O4 | 1.4318 (15) | C12—C13 | 1.386 (3) |
S2—O3 | 1.4335 (15) | C12—C11 | 1.386 (3) |
S2—N2 | 1.6309 (17) | C12—H12 | 0.97 (3) |
S2—C3 | 1.7409 (19) | C11—C10 | 1.380 (3) |
N1—C2 | 1.378 (2) | C11—H11 | 0.93 (3) |
N1—C5 | 1.391 (2) | C10—H10 | 0.94 (3) |
N2—C7 | 1.470 (3) | C6—H6B | 0.95 (3) |
N2—C6 | 1.473 (3) | C6—H6A | 1.00 (3) |
C8—C9 | 1.386 (3) | C6—H6C | 0.94 (3) |
C8—C13 | 1.389 (3) | C13—H13 | 0.89 (3) |
C3—C2 | 1.366 (3) | C7—H7B | 0.97 (2) |
C3—C4 | 1.428 (3) | C7—H7C | 0.96 (3) |
C9—C10 | 1.386 (3) | C7—H7A | 0.99 (3) |
C9—H9 | 0.90 (3) | ||
O1—S1—O2 | 121.63 (9) | C3—C2—N1 | 106.29 (16) |
O1—S1—N1 | 105.21 (8) | C3—C2—H2 | 131.6 (15) |
O2—S1—N1 | 105.07 (8) | N1—C2—H2 | 122.1 (15) |
O1—S1—C8 | 109.24 (9) | C5—C4—C3 | 107.18 (17) |
O2—S1—C8 | 109.51 (9) | C5—C4—H4 | 126.1 (16) |
N1—S1—C8 | 104.77 (9) | C3—C4—H4 | 126.7 (16) |
O4—S2—O3 | 119.76 (9) | C13—C12—C11 | 120.2 (2) |
O4—S2—N2 | 107.45 (9) | C13—C12—H12 | 120.5 (17) |
O3—S2—N2 | 106.59 (9) | C11—C12—H12 | 119.4 (17) |
O4—S2—C3 | 107.21 (9) | C10—C11—C12 | 120.8 (2) |
O3—S2—C3 | 107.34 (9) | C10—C11—H11 | 119.5 (17) |
N2—S2—C3 | 108.03 (9) | C12—C11—H11 | 119.7 (17) |
C2—N1—C5 | 109.96 (16) | C11—C10—C9 | 120.0 (2) |
C2—N1—S1 | 125.42 (13) | C11—C10—H10 | 120.0 (16) |
C5—N1—S1 | 124.53 (14) | C9—C10—H10 | 120.0 (16) |
C7—N2—C6 | 112.49 (18) | N2—C6—H6B | 108.4 (16) |
C7—N2—S2 | 115.50 (14) | N2—C6—H6A | 113.5 (17) |
C6—N2—S2 | 115.69 (14) | H6B—C6—H6A | 109 (2) |
C9—C8—C13 | 122.18 (18) | N2—C6—H6C | 105.7 (17) |
C9—C8—S1 | 118.52 (15) | H6B—C6—H6C | 111 (2) |
C13—C8—S1 | 119.28 (15) | H6A—C6—H6C | 109 (2) |
C2—C3—C4 | 108.83 (17) | C12—C13—C8 | 118.2 (2) |
C2—C3—S2 | 124.14 (15) | C12—C13—H13 | 120.7 (18) |
C4—C3—S2 | 126.88 (15) | C8—C13—H13 | 121.1 (18) |
C8—C9—C10 | 118.6 (2) | N2—C7—H7B | 110.8 (15) |
C8—C9—H9 | 118.5 (16) | N2—C7—H7C | 106.3 (18) |
C10—C9—H9 | 122.9 (16) | H7B—C7—H7C | 112 (2) |
C4—C5—N1 | 107.72 (17) | N2—C7—H7A | 112.1 (16) |
C4—C5—H5 | 133.1 (15) | H7B—C7—H7A | 106 (2) |
N1—C5—H5 | 119.2 (15) | H7C—C7—H7A | 110 (2) |
O1—S1—N1—C2 | 152.01 (16) | O4—S2—C3—C4 | −31.5 (2) |
O2—S1—N1—C2 | 22.53 (18) | O3—S2—C3—C4 | −161.35 (17) |
C8—S1—N1—C2 | −92.85 (17) | N2—S2—C3—C4 | 84.05 (19) |
O1—S1—N1—C5 | −31.49 (18) | C13—C8—C9—C10 | 1.3 (3) |
O2—S1—N1—C5 | −160.97 (16) | S1—C8—C9—C10 | −177.20 (16) |
C8—S1—N1—C5 | 83.65 (17) | C2—N1—C5—C4 | −1.1 (2) |
O4—S2—N2—C7 | −177.60 (15) | S1—N1—C5—C4 | −178.02 (15) |
O3—S2—N2—C7 | −48.07 (17) | C4—C3—C2—N1 | −0.6 (2) |
C3—S2—N2—C7 | 67.02 (17) | S2—C3—C2—N1 | 175.20 (14) |
O4—S2—N2—C6 | 47.99 (18) | C5—N1—C2—C3 | 1.0 (2) |
O3—S2—N2—C6 | 177.53 (16) | S1—N1—C2—C3 | 177.97 (14) |
C3—S2—N2—C6 | −67.38 (17) | N1—C5—C4—C3 | 0.6 (2) |
O1—S1—C8—C9 | 1.74 (19) | C2—C3—C4—C5 | 0.0 (2) |
O2—S1—C8—C9 | 137.21 (16) | S2—C3—C4—C5 | −175.69 (15) |
N1—S1—C8—C9 | −110.55 (16) | C13—C12—C11—C10 | 1.0 (4) |
O1—S1—C8—C13 | −176.78 (16) | C12—C11—C10—C9 | 0.7 (3) |
O2—S1—C8—C13 | −41.32 (19) | C8—C9—C10—C11 | −1.8 (3) |
N1—S1—C8—C13 | 70.93 (18) | C11—C12—C13—C8 | −1.5 (3) |
O4—S2—C3—C2 | 153.46 (17) | C9—C8—C13—C12 | 0.3 (3) |
O3—S2—C3—C2 | 23.6 (2) | S1—C8—C13—C12 | 178.80 (17) |
N2—S2—C3—C2 | −91.01 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.89 (2) | 2.57 (2) | 3.325 (3) | 143 (2) |
C6—H6B···O4 | 0.95 (3) | 2.51 (3) | 2.913 (3) | 105.9 (19) |
C7—H7B···O3 | 0.97 (3) | 2.46 (2) | 2.891 (3) | 106.5 (17) |
C9—H9···O1 | 0.89 (2) | 2.48 (2) | 2.887 (2) | 108.6 (19) |
C10—H10···O2ii | 0.94 (2) | 2.48 (3) | 3.317 (3) | 150 (2) |
C11—H11···O3iii | 0.93 (3) | 2.52 (3) | 3.404 (3) | 160 (2) |
C13—H13···O3iv | 0.89 (3) | 2.46 (3) | 3.349 (3) | 176 (2) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z. |
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