Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001382/ob6340sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001382/ob6340Isup2.hkl |
CCDC reference: 236078
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.042
- wR factor = 0.115
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C13 = 6.24 su 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 3 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 1 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: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); software used to prepare material for publication: CrystalStructure.
C15H15NO2S | F(000) = 1152.00 |
Mr = 273.35 | Dx = 1.311 Mg m−3 |
Monoclinic, P21/n | Melting point: 164 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.7107 Å |
a = 20.961 (1) Å | Cell parameters from 16675 reflections |
b = 9.7061 (5) Å | θ = 2.3–27.4° |
c = 20.894 (1) Å | µ = 0.23 mm−1 |
β = 139.336 (1)° | T = 298 K |
V = 2770.0 (3) Å3 | Prism, colorless |
Z = 8 | 0.29 × 0.28 × 0.20 mm |
Rigaku R-AXIS RAPID diffractometer | 3764 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.027 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −27→27 |
Tmin = 0.842, Tmax = 0.955 | k = −12→12 |
47104 measured reflections | l = −27→27 |
6218 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = (4Fo2)/[0.002Fo2 + 1.6σ(Fo2)] |
wR(F2) = 0.115 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.41 e Å−3 |
3776 reflections | Δρmin = −0.30 e Å−3 |
373 parameters |
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 | ||
S1 | 0.17543 (4) | 0.51139 (5) | 0.26933 (4) | 0.0391 (1) | |
S2 | 0.26337 (4) | 0.52331 (5) | 0.67238 (4) | 0.0406 (2) | |
O1 | 0.3851 (1) | 0.5149 (2) | 0.4503 (1) | 0.0719 (6) | |
O2 | 0.1909 (1) | 0.6061 (2) | 0.2262 (1) | 0.0556 (5) | |
O3 | 0.4415 (1) | 0.5320 (2) | 0.8805 (1) | 0.0656 (5) | |
O4 | 0.2191 (1) | 0.6187 (2) | 0.6863 (1) | 0.0612 (5) | |
N1 | 0.4209 (1) | 0.3495 (2) | 0.4060 (2) | 0.0544 (6) | |
H201 | 0.4877 | 0.3762 | 0.4541 | 0.059* | |
H202 | 0.3976 | 0.2739 | 0.3637 | 0.059* | |
N2 | 0.4097 (1) | 0.3539 (2) | 0.9222 (1) | 0.0530 (6) | |
H401 | 0.4603 | 0.3782 | 0.9898 | 0.059* | |
H402 | 0.3702 | 0.2752 | 0.9002 | 0.058* | |
C1 | 0.2556 (1) | 0.3668 (2) | 0.3188 (2) | 0.0432 (6) | |
H101 | 0.2409 | 0.3230 | 0.2681 | 0.047* | |
H102 | 0.2472 | 0.3029 | 0.3465 | 0.047* | |
C2 | 0.3606 (2) | 0.4176 (2) | 0.3978 (2) | 0.0435 (6) | |
C3 | 0.0605 (1) | 0.4197 (2) | 0.1651 (2) | 0.0393 (6) | |
H3 | 0.0669 | 0.3761 | 0.1295 | 0.045* | |
C4 | −0.0216 (2) | 0.5235 (2) | 0.0975 (2) | 0.0410 (6) | |
C5 | −0.0918 (2) | 0.5029 (3) | −0.0033 (2) | 0.0579 (8) | |
H5 | −0.0856 | 0.4266 | −0.0267 | 0.071* | |
C6 | −0.1693 (2) | 0.5940 (4) | −0.0681 (2) | 0.080 (1) | |
H6 | −0.2180 | 0.5786 | −0.1368 | 0.092* | |
C7 | −0.1771 (2) | 0.7047 (4) | −0.0350 (3) | 0.084 (1) | |
H7 | −0.2300 | 0.7674 | −0.0802 | 0.091* | |
C8 | −0.1087 (2) | 0.7266 (3) | 0.0635 (3) | 0.073 (1) | |
H8 | −0.1146 | 0.8039 | 0.0866 | 0.082* | |
C9 | −0.0310 (2) | 0.6363 (2) | 0.1301 (2) | 0.0536 (7) | |
H9 | 0.0165 | 0.6511 | 0.1987 | 0.058* | |
C10 | 0.0449 (1) | 0.3070 (2) | 0.2024 (1) | 0.0374 (5) | |
C11 | 0.0478 (2) | 0.1708 (3) | 0.1859 (2) | 0.0568 (8) | |
H11 | 0.0589 | 0.1495 | 0.1507 | 0.069* | |
C12 | 0.0338 (2) | 0.0669 (3) | 0.2201 (3) | 0.076 (1) | |
H12 | 0.0352 | −0.0267 | 0.2079 | 0.086* | |
C13 | 0.0174 (2) | 0.0980 (3) | 0.2705 (2) | 0.0669 (8) | |
H13 | 0.0084 | 0.0267 | 0.2943 | 0.073* | |
C14 | 0.0157 (2) | 0.2329 (3) | 0.2878 (2) | 0.0565 (7) | |
H14 | 0.0042 | 0.2550 | 0.3228 | 0.064* | |
C15 | 0.0287 (2) | 0.3363 (3) | 0.2543 (2) | 0.0454 (6) | |
H15 | 0.0270 | 0.4297 | 0.2665 | 0.051* | |
C16 | 0.3115 (2) | 0.3807 (2) | 0.7532 (1) | 0.0425 (6) | |
H301 | 0.3359 | 0.3134 | 0.7429 | 0.047* | |
H302 | 0.2611 | 0.3413 | 0.7403 | 0.047* | |
C17 | 0.3941 (2) | 0.4298 (2) | 0.8588 (2) | 0.0414 (6) | |
C18 | 0.1595 (2) | 0.4303 (2) | 0.5580 (1) | 0.0376 (5) | |
H18 | 0.1213 | 0.3941 | 0.5631 | 0.044* | |
C19 | 0.0957 (2) | 0.5312 (2) | 0.4727 (2) | 0.0416 (6) | |
C20 | −0.0050 (2) | 0.5143 (3) | 0.3987 (2) | 0.0586 (8) | |
H20 | −0.0318 | 0.4436 | 0.4044 | 0.069* | |
C21 | −0.0657 (2) | 0.6017 (4) | 0.3174 (2) | 0.082 (1) | |
H21 | −0.1347 | 0.5894 | 0.2660 | 0.088* | |
C22 | −0.0261 (3) | 0.7044 (4) | 0.3107 (3) | 0.084 (1) | |
H22 | −0.0678 | 0.7642 | 0.2554 | 0.096* | |
C23 | 0.0713 (3) | 0.7220 (3) | 0.3823 (2) | 0.077 (1) | |
H23 | 0.0977 | 0.7934 | 0.3765 | 0.089* | |
C24 | 0.1331 (2) | 0.6359 (3) | 0.4636 (2) | 0.0592 (8) | |
H24 | 0.2020 | 0.6487 | 0.5140 | 0.066* | |
C25 | 0.1956 (1) | 0.3097 (2) | 0.5462 (1) | 0.0360 (5) | |
C26 | 0.1765 (2) | 0.1771 (2) | 0.5525 (2) | 0.0477 (7) | |
H26 | 0.1406 | 0.1636 | 0.5637 | 0.058* | |
C27 | 0.2104 (2) | 0.0656 (3) | 0.5435 (2) | 0.0639 (8) | |
H27 | 0.1966 | −0.0256 | 0.5470 | 0.070* | |
C28 | 0.2625 (2) | 0.0856 (3) | 0.5279 (2) | 0.0654 (9) | |
H28 | 0.2859 | 0.0090 | 0.5220 | 0.074* | |
C29 | 0.2821 (2) | 0.2167 (3) | 0.5224 (2) | 0.0587 (8) | |
H29 | 0.3188 | 0.2301 | 0.5121 | 0.070* | |
C30 | 0.2485 (2) | 0.3282 (3) | 0.5306 (2) | 0.0467 (6) | |
H30 | 0.2619 | 0.4189 | 0.5263 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0332 (3) | 0.0326 (3) | 0.0422 (3) | −0.0021 (2) | 0.0260 (3) | −0.0017 (2) |
S2 | 0.0455 (3) | 0.0324 (3) | 0.0343 (3) | −0.0001 (2) | 0.0275 (3) | −0.0017 (2) |
O1 | 0.0382 (9) | 0.070 (1) | 0.072 (1) | −0.0054 (9) | 0.032 (1) | −0.034 (1) |
O2 | 0.0449 (9) | 0.0446 (9) | 0.066 (1) | −0.0024 (8) | 0.0386 (9) | 0.0128 (8) |
O3 | 0.069 (1) | 0.061 (1) | 0.0389 (9) | −0.031 (1) | 0.033 (1) | −0.0096 (8) |
O4 | 0.075 (1) | 0.046 (1) | 0.048 (1) | 0.0180 (9) | 0.042 (1) | −0.0012 (8) |
N1 | 0.037 (1) | 0.050 (1) | 0.061 (1) | −0.0050 (9) | 0.033 (1) | −0.019 (1) |
N2 | 0.060 (1) | 0.050 (1) | 0.036 (1) | −0.019 (1) | 0.033 (1) | −0.0076 (9) |
C1 | 0.037 (1) | 0.033 (1) | 0.048 (1) | 0.0009 (9) | 0.029 (1) | −0.000 (1) |
C2 | 0.035 (1) | 0.038 (1) | 0.043 (1) | −0.000 (1) | 0.025 (1) | −0.004 (1) |
C3 | 0.036 (1) | 0.040 (1) | 0.037 (1) | −0.005 (1) | 0.026 (1) | −0.005 (1) |
C4 | 0.033 (1) | 0.044 (1) | 0.042 (1) | −0.0030 (9) | 0.027 (1) | 0.008 (1) |
C5 | 0.044 (1) | 0.087 (2) | 0.046 (1) | −0.002 (1) | 0.035 (1) | 0.009 (1) |
C6 | 0.046 (2) | 0.133 (3) | 0.050 (2) | 0.009 (2) | 0.033 (1) | 0.037 (2) |
C7 | 0.050 (2) | 0.086 (2) | 0.092 (3) | 0.020 (2) | 0.047 (2) | 0.058 (2) |
C8 | 0.054 (2) | 0.043 (1) | 0.109 (3) | 0.007 (1) | 0.058 (2) | 0.018 (2) |
C9 | 0.041 (1) | 0.043 (1) | 0.059 (2) | −0.001 (1) | 0.033 (1) | 0.003 (1) |
C10 | 0.030 (1) | 0.034 (1) | 0.036 (1) | −0.0036 (9) | 0.021 (1) | −0.0007 (9) |
C11 | 0.061 (2) | 0.041 (1) | 0.071 (2) | −0.010 (1) | 0.050 (2) | −0.011 (1) |
C12 | 0.082 (2) | 0.031 (1) | 0.102 (2) | −0.006 (1) | 0.066 (2) | −0.001 (1) |
C13 | 0.057 (2) | 0.057 (2) | 0.068 (2) | −0.004 (1) | 0.043 (2) | 0.017 (1) |
C14 | 0.049 (1) | 0.068 (2) | 0.044 (1) | −0.008 (1) | 0.033 (1) | 0.004 (1) |
C15 | 0.041 (1) | 0.044 (1) | 0.044 (1) | −0.005 (1) | 0.030 (1) | −0.003 (1) |
C16 | 0.046 (1) | 0.034 (1) | 0.036 (1) | −0.001 (1) | 0.028 (1) | −0.001 (1) |
C17 | 0.042 (1) | 0.037 (1) | 0.035 (1) | −0.004 (1) | 0.026 (1) | −0.003 (1) |
C18 | 0.037 (1) | 0.037 (1) | 0.035 (1) | −0.000 (1) | 0.026 (1) | −0.003 (1) |
C19 | 0.044 (1) | 0.040 (1) | 0.036 (1) | 0.009 (1) | 0.029 (1) | −0.001 (1) |
C20 | 0.048 (1) | 0.077 (2) | 0.047 (1) | 0.013 (1) | 0.035 (1) | 0.001 (1) |
C21 | 0.048 (2) | 0.123 (3) | 0.047 (2) | 0.035 (2) | 0.029 (1) | 0.006 (2) |
C22 | 0.099 (3) | 0.084 (2) | 0.058 (2) | 0.052 (2) | 0.057 (2) | 0.027 (2) |
C23 | 0.104 (3) | 0.055 (2) | 0.062 (2) | 0.023 (2) | 0.061 (2) | 0.018 (1) |
C24 | 0.066 (2) | 0.047 (1) | 0.050 (1) | 0.007 (1) | 0.040 (1) | 0.006 (1) |
C25 | 0.033 (1) | 0.038 (1) | 0.028 (1) | 0.0028 (9) | 0.021 (1) | −0.0019 (9) |
C26 | 0.054 (1) | 0.041 (1) | 0.050 (1) | −0.000 (1) | 0.040 (1) | −0.005 (1) |
C27 | 0.071 (2) | 0.038 (1) | 0.065 (2) | 0.004 (1) | 0.047 (2) | −0.005 (1) |
C28 | 0.063 (2) | 0.062 (2) | 0.060 (2) | 0.021 (1) | 0.044 (2) | −0.004 (1) |
C29 | 0.045 (1) | 0.083 (2) | 0.048 (1) | 0.014 (1) | 0.035 (1) | 0.001 (1) |
C30 | 0.042 (1) | 0.052 (1) | 0.042 (1) | 0.004 (1) | 0.031 (1) | 0.001 (1) |
S1—O2 | 1.485 (3) | C12—C13 | 1.368 (9) |
S1—C1 | 1.797 (2) | C12—H12 | 0.950 |
S1—C3 | 1.838 (2) | C13—C14 | 1.366 (5) |
S2—O4 | 1.487 (3) | C13—H13 | 0.950 |
S2—C16 | 1.789 (2) | C14—C15 | 1.365 (5) |
S2—C18 | 1.837 (2) | C14—H14 | 0.950 |
O1—C2 | 1.226 (4) | C15—H15 | 0.950 |
O3—C17 | 1.222 (3) | C16—C17 | 1.515 (3) |
N1—C2 | 1.317 (5) | C16—H301 | 0.950 |
N1—H201 | 0.950 | C16—H302 | 0.950 |
N1—H202 | 0.950 | C18—C19 | 1.520 (3) |
N2—C17 | 1.322 (5) | C18—C25 | 1.513 (4) |
N2—H401 | 0.950 | C18—H18 | 0.950 |
N2—H402 | 0.950 | C19—C20 | 1.386 (4) |
C1—C2 | 1.517 (3) | C19—C24 | 1.383 (5) |
C1—H101 | 0.950 | C20—C21 | 1.394 (4) |
C1—H102 | 0.950 | C20—H20 | 0.950 |
C3—C4 | 1.512 (3) | C21—C22 | 1.371 (8) |
C3—C10 | 1.515 (5) | C21—H21 | 0.950 |
C3—H3 | 0.950 | C22—C23 | 1.343 (6) |
C4—C5 | 1.394 (4) | C22—H22 | 0.950 |
C4—C9 | 1.379 (5) | C23—C24 | 1.386 (4) |
C5—C6 | 1.384 (4) | C23—H23 | 0.950 |
C5—H5 | 0.950 | C24—H24 | 0.950 |
C6—C7 | 1.353 (7) | C25—C26 | 1.384 (4) |
C6—H6 | 0.950 | C25—C30 | 1.383 (6) |
C7—C8 | 1.364 (6) | C26—C27 | 1.384 (6) |
C7—H7 | 0.950 | C26—H26 | 0.950 |
C8—C9 | 1.385 (3) | C27—C28 | 1.370 (8) |
C8—H8 | 0.950 | C27—H27 | 0.950 |
C9—H9 | 0.950 | C28—C29 | 1.369 (5) |
C10—C11 | 1.379 (4) | C28—H28 | 0.950 |
C10—C15 | 1.390 (6) | C29—C30 | 1.372 (5) |
C11—C12 | 1.388 (7) | C29—H29 | 0.950 |
C11—H11 | 0.950 | C30—H30 | 0.950 |
O2—S1—C1 | 107.1 (2) | C15—C14—H14 | 119.6 |
O2—S1—C3 | 105.9 (1) | C15—C14—C13 | 120.9 (5) |
C1—S1—C3 | 96.7 (1) | H14—C14—C13 | 119.5 |
O4—S2—C16 | 106.6 (2) | H15—C15—C10 | 119.1 |
O4—S2—C18 | 105.1 (1) | H15—C15—C14 | 120.1 |
C16—S2—C18 | 96.4 (1) | C10—C15—C14 | 120.9 (3) |
C2—N1—H201 | 120.0 | C17—C16—H301 | 109.2 |
C2—N1—H202 | 120.0 | C17—C16—H302 | 109.7 |
H201—N1—H202 | 120.0 | C17—C16—S2 | 109.5 (1) |
C17—N2—H401 | 120.0 | H301—C16—H302 | 109.5 |
C17—N2—H402 | 120.0 | H301—C16—S2 | 109.4 |
H401—N2—H402 | 120.0 | H302—C16—S2 | 109.5 |
C2—C1—H101 | 109.6 | O3—C17—N2 | 124.5 (2) |
C2—C1—H102 | 109.6 | O3—C17—C16 | 120.4 (3) |
C2—C1—S1 | 108.9 (2) | N2—C17—C16 | 115.1 (2) |
H101—C1—H102 | 109.5 | C19—C18—C25 | 114.2 (3) |
H101—C1—S1 | 109.7 | C19—C18—H18 | 107.6 |
H102—C1—S1 | 109.6 | C19—C18—S2 | 109.2 (1) |
O1—C2—N1 | 124.1 (2) | C25—C18—H18 | 107.5 |
O1—C2—C1 | 120.1 (3) | C25—C18—S2 | 110.3 (2) |
N1—C2—C1 | 115.8 (2) | H18—C18—S2 | 107.8 |
C4—C3—C10 | 115.1 (3) | C20—C19—C24 | 118.4 (2) |
C4—C3—H3 | 107.6 | C20—C19—C18 | 118.2 (3) |
C4—C3—S1 | 108.9 (1) | C24—C19—C18 | 123.3 (2) |
C10—C3—H3 | 107.2 | C21—C20—H20 | 120.8 |
C10—C3—S1 | 109.9 (2) | C21—C20—C19 | 119.8 (4) |
H3—C3—S1 | 107.8 | H20—C20—C19 | 119.4 |
C5—C4—C9 | 118.5 (2) | C22—C21—H21 | 119.7 |
C5—C4—C3 | 117.7 (3) | C22—C21—C20 | 120.2 (3) |
C9—C4—C3 | 123.8 (2) | H21—C21—C20 | 120.1 |
C6—C5—H5 | 120.9 | C23—C22—H22 | 119.8 |
C6—C5—C4 | 119.8 (4) | C23—C22—C21 | 120.4 (3) |
H5—C5—C4 | 119.4 | H22—C22—C21 | 119.8 |
C7—C6—H6 | 119.3 | C24—C23—H23 | 120.2 |
C7—C6—C5 | 121.0 (3) | C24—C23—C22 | 120.4 (5) |
H6—C6—C5 | 119.7 | H23—C23—C22 | 119.4 |
C8—C7—H7 | 119.9 | H24—C24—C19 | 119.1 |
C8—C7—C6 | 119.9 (3) | H24—C24—C23 | 120.1 |
H7—C7—C6 | 120.2 | C19—C24—C23 | 120.8 (3) |
C9—C8—H8 | 119.8 | C26—C25—C30 | 119.0 (3) |
C9—C8—C7 | 120.4 (4) | C26—C25—C18 | 119.1 (4) |
H8—C8—C7 | 119.8 | C30—C25—C18 | 121.9 (2) |
H9—C9—C4 | 119.1 | C27—C26—H26 | 120.6 |
H9—C9—C8 | 120.5 | C27—C26—C25 | 119.9 (4) |
C4—C9—C8 | 120.4 (3) | H26—C26—C25 | 119.5 |
C11—C10—C15 | 118.2 (3) | C28—C27—H27 | 119.5 |
C11—C10—C3 | 119.8 (4) | C28—C27—C26 | 120.4 (3) |
C15—C10—C3 | 122.0 (2) | H27—C27—C26 | 120.1 |
C12—C11—H11 | 120.8 | C29—C28—H28 | 119.8 |
C12—C11—C10 | 120.2 (5) | C29—C28—C27 | 119.8 (4) |
H11—C11—C10 | 119.0 | H28—C28—C27 | 120.4 |
C13—C12—H12 | 119.6 | C30—C29—H29 | 120.1 |
C13—C12—C11 | 120.7 (3) | C30—C29—C28 | 120.4 (5) |
H12—C12—C11 | 119.7 | H29—C29—C28 | 119.5 |
C14—C13—H13 | 120.4 | H30—C30—C25 | 119.4 |
C14—C13—C12 | 119.2 (4) | H30—C30—C29 | 120.1 |
H13—C13—C12 | 120.4 | C25—C30—C29 | 120.5 (3) |
O2—S1—C1—C2 | 60.8 (3) | O4—S2—C16—C17 | −65.0 (3) |
C3—S1—C1—C2 | 169.8 (3) | C18—S2—C16—C17 | −172.8 (3) |
O2—S1—C3—C4 | −60.3 (3) | O4—S2—C18—C19 | 65.3 (3) |
O2—S1—C3—C10 | 172.7 (2) | O4—S2—C18—C25 | −168.4 (2) |
C1—S1—C3—C4 | −170.3 (3) | C16—S2—C18—C19 | 174.4 (3) |
C1—S1—C3—C10 | 62.8 (2) | C16—S2—C18—C25 | −59.3 (2) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register