Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013140/sj6075sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013140/sj6075IVsup2.hkl |
CCDC reference: 274627
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.091
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT391_ALERT_3_B Deviating Methyl C16 H-C-H Bond Angle ...... 98.00 Deg.
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT350_ALERT_3_C Short C-H Bond (0.96A) C14 - H142 ... 0.78 Ang. PLAT351_ALERT_3_C Long C-H Bond (0.96A) C13 - H132 ... 1.11 Ang.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 28.66 From the CIF: _reflns_number_total 3439 Count of symmetry unique reflns 2294 Completeness (_total/calc) 149.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1145 Fraction of Friedel pairs measured 0.499 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Kuma Diffraction, 2001); cell refinement: CrysAlis RED (Kuma Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and XP (Sheldrick, 1989); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).
C18H16N2O4S | F(000) = 372 |
Mr = 356.39 | Dx = 1.401 Mg m−3 |
Monoclinic, P21 | Melting point = 474–476 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 7.618 (1) Å | Cell parameters from 4038 reflections |
b = 10.280 (2) Å | θ = 1.9–24.5° |
c = 10.936 (1) Å | µ = 0.22 mm−1 |
β = 99.55 (1)° | T = 293 K |
V = 844.6 (2) Å3 | Prism, yellow |
Z = 2 | 0.80 × 0.51 × 0.13 mm |
Kuma KM-4 diffractometer | 3439 independent reflections |
Radiation source: fine-focus sealed tube | 2962 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
ω scans | θmax = 28.7°, θmin = 3.4° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | h = −10→10 |
Tmin = 0.890, Tmax = 0.975 | k = −9→13 |
10762 measured reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | Only H-atom coordinates refined |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.091 | (Δ/σ)max < 0.001 |
S = 0.96 | Δρmax = 0.22 e Å−3 |
3439 reflections | Δρmin = −0.31 e Å−3 |
275 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.028 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1315 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.05 (6) |
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) 7.2757 (0.0022) x - 2.9015 (0.0077) y - 0.7575 (0.0075) z = 2.1928 (0.0029) * 0.0014 (0.0013) C5 * 0.0152 (0.0014) C6 * -0.0173 (0.0013) C7 * 0.0010 (0.0013) N8 * 0.0166 (0.0013) C9 * -0.0169 (0.0012) C10 0.0058 (0.0034) C15 - 0.0923 (0.0039) C16 Rms deviation of fitted atoms = 0.0135 6.7380 (0.0035) x + 4.7084 (0.0084) y - 0.6455 (0.0094) z = 3.0120 (0.0020) A ngle to previous plane (with approximate e.s.d.) = 43.65 (0.05) * -0.0071 (0.0014) C21 * 0.0032 (0.0015) C22 * 0.0023 (0.0016) C23 * -0.0041 (0.0017) C24 * 0.0002 (0.0016) C25 * 0.0054 (0.0014) C26 Rms deviation of fitted atoms = 0.0043 6.4980 (0.0033) x - 4.4996 (0.0048) y - 4.6137 (0.0090) z = 1.6019 (0.0015) A ngle to previous plane (with approximate e.s.d.) = 58.08 (0.05) * 0.1115 (0.0011) C10 * 0.0041 (0.0014) C4 * -0.1296 (0.0010) O4 * -0.0424 (0.0013) C3 * -0.0972 (0.0013) C11 * 0.1535 (0.0011) C21 Rms deviation of fitted atoms = 0.1033 |
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 | 0.30652 (7) | −0.06487 (5) | 0.37002 (4) | 0.04686 (16) | |
O1S | 0.1473 (3) | 0.0096 (2) | 0.36594 (17) | 0.0704 (5) | |
O2S | 0.4185 (2) | −0.0849 (2) | 0.48637 (11) | 0.0717 (6) | |
O4 | 0.15428 (19) | −0.09136 (15) | −0.01273 (11) | 0.0494 (4) | |
O12 | 0.4559 (2) | 0.22874 (15) | 0.14683 (12) | 0.0496 (4) | |
N2 | 0.4347 (2) | −0.00717 (16) | 0.27561 (13) | 0.0387 (4) | |
N8 | 0.2162 (2) | −0.31044 (19) | 0.36942 (14) | 0.0430 (4) | |
C3 | 0.3524 (2) | 0.01004 (19) | 0.14847 (15) | 0.0337 (4) | |
C4 | 0.2428 (2) | −0.09977 (18) | 0.09110 (15) | 0.0336 (4) | |
C5 | 0.1772 (2) | −0.34072 (19) | 0.11027 (16) | 0.0353 (4) | |
C6 | 0.1468 (3) | −0.4419 (2) | 0.18798 (19) | 0.0415 (4) | |
H61 | 0.116 (4) | −0.519 (3) | 0.163 (2) | 0.062* | |
C7 | 0.1626 (2) | −0.4245 (2) | 0.31608 (17) | 0.0422 (5) | |
C9 | 0.2484 (2) | −0.21533 (19) | 0.29393 (16) | 0.0373 (4) | |
C10 | 0.2285 (2) | −0.22007 (19) | 0.16504 (15) | 0.0327 (4) | |
C11 | 0.3784 (2) | 0.12130 (18) | 0.08844 (16) | 0.0355 (4) | |
C13 | 0.4909 (5) | 0.2240 (3) | 0.2799 (2) | 0.0631 (7) | |
H131 | 0.371 (4) | 0.234 (4) | 0.308 (3) | 0.095* | |
H132 | 0.575 (4) | 0.309 (4) | 0.315 (3) | 0.095* | |
C14 | 0.5626 (3) | 0.0956 (2) | 0.3228 (2) | 0.0540 (6) | |
H141 | 0.680 (4) | 0.080 (3) | 0.284 (3) | 0.081* | |
H142 | 0.582 (4) | 0.081 (3) | 0.394 (3) | 0.081* | |
C15 | 0.1537 (3) | −0.3651 (2) | −0.02745 (19) | 0.0464 (5) | |
H151 | 0.164 (4) | −0.452 (3) | −0.046 (3) | 0.070* | |
H152 | 0.246 (4) | −0.319 (3) | −0.068 (3) | 0.070* | |
H153 | 0.031 (4) | −0.325 (3) | −0.069 (3) | 0.070* | |
C16 | 0.1181 (4) | −0.5317 (3) | 0.3985 (3) | 0.0594 (7) | |
H161 | 0.223 (4) | −0.571 (4) | 0.446 (3) | 0.089* | |
H162 | 0.047 (4) | −0.582 (4) | 0.352 (3) | 0.089* | |
H163 | 0.071 (4) | −0.496 (4) | 0.464 (3) | 0.089* | |
C21 | 0.3386 (2) | 0.14716 (19) | −0.04710 (16) | 0.0350 (4) | |
C22 | 0.3916 (3) | 0.0618 (2) | −0.13270 (18) | 0.0419 (4) | |
H221 | 0.451 (3) | −0.016 (3) | −0.111 (2) | 0.063* | |
C23 | 0.3587 (3) | 0.0915 (3) | −0.2579 (2) | 0.0527 (5) | |
H231 | 0.386 (4) | 0.038 (3) | −0.322 (3) | 0.079* | |
C24 | 0.2731 (3) | 0.2072 (3) | −0.2976 (2) | 0.0569 (6) | |
H241 | 0.250 (4) | 0.233 (4) | −0.380 (3) | 0.085* | |
C25 | 0.2223 (3) | 0.2924 (3) | −0.2139 (2) | 0.0543 (6) | |
H251 | 0.162 (4) | 0.372 (3) | −0.235 (3) | 0.081* | |
C26 | 0.2558 (3) | 0.2627 (2) | −0.0878 (2) | 0.0449 (5) | |
H216 | 0.222 (4) | 0.319 (3) | −0.031 (3) | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0675 (3) | 0.0460 (3) | 0.0294 (2) | −0.0055 (3) | 0.01473 (18) | −0.0067 (2) |
O1S | 0.0839 (11) | 0.0602 (11) | 0.0782 (11) | 0.0053 (9) | 0.0460 (9) | −0.0125 (9) |
O2S | 0.1128 (13) | 0.0740 (14) | 0.0249 (6) | −0.0316 (12) | 0.0013 (7) | −0.0032 (8) |
O4 | 0.0599 (8) | 0.0454 (9) | 0.0361 (6) | −0.0085 (7) | −0.0121 (6) | 0.0076 (6) |
O12 | 0.0763 (10) | 0.0344 (8) | 0.0374 (7) | −0.0117 (7) | 0.0073 (6) | −0.0074 (6) |
N2 | 0.0507 (9) | 0.0395 (9) | 0.0245 (7) | −0.0063 (7) | 0.0020 (6) | −0.0049 (6) |
N8 | 0.0466 (9) | 0.0495 (11) | 0.0329 (8) | −0.0045 (8) | 0.0066 (6) | 0.0058 (7) |
C3 | 0.0401 (9) | 0.0339 (10) | 0.0264 (7) | −0.0002 (8) | 0.0034 (7) | −0.0027 (7) |
C4 | 0.0358 (8) | 0.0341 (10) | 0.0302 (7) | 0.0008 (7) | 0.0037 (6) | −0.0004 (7) |
C5 | 0.0357 (9) | 0.0330 (10) | 0.0366 (9) | −0.0002 (7) | 0.0042 (7) | −0.0012 (7) |
C6 | 0.0430 (10) | 0.0358 (11) | 0.0446 (10) | −0.0036 (8) | 0.0040 (8) | 0.0020 (9) |
C7 | 0.0419 (10) | 0.0442 (12) | 0.0401 (10) | −0.0025 (9) | 0.0055 (8) | 0.0083 (9) |
C9 | 0.0423 (10) | 0.0398 (11) | 0.0293 (8) | −0.0012 (8) | 0.0044 (7) | −0.0012 (8) |
C10 | 0.0347 (8) | 0.0349 (10) | 0.0283 (8) | 0.0002 (7) | 0.0041 (6) | −0.0005 (7) |
C11 | 0.0433 (9) | 0.0304 (10) | 0.0330 (8) | −0.0006 (8) | 0.0072 (7) | −0.0064 (7) |
C13 | 0.102 (2) | 0.0459 (14) | 0.0389 (11) | −0.0163 (15) | 0.0040 (11) | −0.0167 (10) |
C14 | 0.0708 (15) | 0.0539 (15) | 0.0335 (9) | −0.0186 (12) | −0.0021 (10) | −0.0079 (10) |
C15 | 0.0663 (14) | 0.0387 (11) | 0.0345 (10) | −0.0072 (10) | 0.0092 (9) | −0.0071 (8) |
C16 | 0.0700 (15) | 0.0543 (17) | 0.0534 (13) | −0.0118 (12) | 0.0091 (11) | 0.0154 (11) |
C21 | 0.0393 (9) | 0.0324 (9) | 0.0332 (8) | −0.0051 (7) | 0.0057 (7) | 0.0000 (7) |
C22 | 0.0510 (11) | 0.0380 (11) | 0.0370 (9) | 0.0005 (9) | 0.0086 (8) | −0.0038 (8) |
C23 | 0.0649 (13) | 0.0565 (15) | 0.0371 (10) | −0.0088 (11) | 0.0102 (9) | −0.0049 (10) |
C24 | 0.0641 (13) | 0.0652 (17) | 0.0393 (11) | −0.0156 (12) | 0.0019 (10) | 0.0164 (11) |
C25 | 0.0561 (13) | 0.0472 (14) | 0.0580 (13) | −0.0025 (11) | 0.0049 (10) | 0.0191 (11) |
C26 | 0.0529 (11) | 0.0339 (11) | 0.0495 (11) | −0.0009 (9) | 0.0129 (9) | 0.0017 (9) |
S1—O2S | 1.4244 (15) | C13—C14 | 1.475 (4) |
S1—O1S | 1.429 (2) | C13—H131 | 1.02 (3) |
S1—N2 | 1.6450 (17) | C13—H132 | 1.11 (4) |
S1—C9 | 1.777 (2) | C14—H141 | 1.06 (3) |
O4—C4 | 1.2236 (19) | C14—H142 | 0.79 (3) |
O12—C11 | 1.361 (2) | C15—H151 | 0.92 (3) |
O12—C13 | 1.437 (3) | C15—H152 | 1.01 (3) |
N2—C3 | 1.438 (2) | C15—H153 | 1.05 (3) |
N2—C14 | 1.471 (3) | C16—H161 | 0.97 (3) |
N8—C9 | 1.329 (3) | C16—H162 | 0.85 (4) |
N8—C7 | 1.343 (3) | C16—H163 | 0.93 (4) |
C3—C11 | 1.350 (3) | C21—C26 | 1.383 (3) |
C3—C4 | 1.480 (2) | C21—C22 | 1.391 (3) |
C4—C10 | 1.491 (3) | C22—C23 | 1.384 (3) |
C5—C6 | 1.386 (3) | C22—H221 | 0.93 (3) |
C5—C10 | 1.404 (3) | C23—C24 | 1.390 (4) |
C5—C15 | 1.508 (3) | C23—H231 | 0.94 (3) |
C6—C7 | 1.397 (3) | C24—C25 | 1.368 (4) |
C6—H61 | 0.86 (3) | C24—H241 | 0.93 (3) |
C7—C16 | 1.498 (3) | C25—C26 | 1.394 (3) |
C9—C10 | 1.393 (2) | C25—H251 | 0.94 (3) |
C11—C21 | 1.487 (2) | C26—H216 | 0.92 (3) |
O2S—S1—O1S | 119.00 (11) | C14—C13—H132 | 115.8 (18) |
O2S—S1—N2 | 106.43 (9) | H131—C13—H132 | 108 (3) |
O1S—S1—N2 | 112.11 (10) | N2—C14—C13 | 110.02 (19) |
O2S—S1—C9 | 111.00 (11) | N2—C14—H141 | 108.0 (18) |
O1S—S1—C9 | 107.91 (11) | C13—C14—H141 | 107.4 (19) |
N2—S1—C9 | 98.50 (8) | N2—C14—H142 | 102 (2) |
C11—O12—C13 | 116.16 (17) | C13—C14—H142 | 119 (3) |
C3—N2—C14 | 114.06 (16) | H141—C14—H142 | 110 (3) |
C3—N2—S1 | 116.23 (12) | C5—C15—H151 | 112.1 (18) |
C14—N2—S1 | 117.82 (13) | C5—C15—H152 | 112.7 (15) |
C9—N8—C7 | 116.54 (16) | H151—C15—H152 | 106 (3) |
C11—C3—N2 | 119.93 (16) | C5—C15—H153 | 108.5 (16) |
C11—C3—C4 | 123.92 (15) | H151—C15—H153 | 113 (2) |
N2—C3—C4 | 116.15 (15) | H152—C15—H153 | 105 (2) |
O4—C4—C3 | 121.64 (16) | C7—C16—H161 | 113 (2) |
O4—C4—C10 | 118.90 (16) | C7—C16—H162 | 106 (2) |
C3—C4—C10 | 119.29 (14) | H161—C16—H162 | 117 (3) |
C6—C5—C10 | 117.63 (17) | C7—C16—H163 | 109 (2) |
C6—C5—C15 | 118.90 (19) | H161—C16—H163 | 98 (3) |
C10—C5—C15 | 123.47 (17) | H162—C16—H163 | 114 (3) |
C5—C6—C7 | 121.6 (2) | C26—C21—C22 | 119.54 (18) |
C5—C6—H61 | 124.3 (18) | C26—C21—C11 | 118.74 (17) |
C7—C6—H61 | 114.1 (18) | C22—C21—C11 | 121.62 (17) |
N8—C7—C6 | 121.09 (18) | C23—C22—C21 | 120.1 (2) |
N8—C7—C16 | 117.64 (19) | C23—C22—H221 | 116.5 (17) |
C6—C7—C16 | 121.3 (2) | C21—C22—H221 | 123.5 (17) |
N8—C9—C10 | 127.06 (19) | C22—C23—C24 | 119.7 (2) |
N8—C9—S1 | 114.01 (13) | C22—C23—H231 | 125 (2) |
C10—C9—S1 | 118.74 (14) | C24—C23—H231 | 115 (2) |
C9—C10—C5 | 115.99 (17) | C25—C24—C23 | 120.6 (2) |
C9—C10—C4 | 120.94 (17) | C25—C24—H241 | 116 (2) |
C5—C10—C4 | 122.77 (15) | C23—C24—H241 | 123 (2) |
C3—C11—O12 | 123.16 (16) | C24—C25—C26 | 119.7 (2) |
C3—C11—C21 | 127.92 (16) | C24—C25—H251 | 124.9 (18) |
O12—C11—C21 | 108.87 (16) | C26—C25—H251 | 115.4 (18) |
O12—C13—C14 | 110.4 (2) | C21—C26—C25 | 120.3 (2) |
O12—C13—H131 | 106.1 (17) | C21—C26—H216 | 119.3 (17) |
C14—C13—H131 | 107 (2) | C25—C26—H216 | 120.4 (17) |
O12—C13—H132 | 108.5 (18) | ||
O2S—S1—N2—C3 | 174.79 (15) | S1—C9—C10—C4 | −4.3 (2) |
O1S—S1—N2—C3 | −53.51 (17) | C6—C5—C10—C9 | 1.6 (2) |
C9—S1—N2—C3 | 59.84 (15) | C15—C5—C10—C9 | −178.39 (18) |
O2S—S1—N2—C14 | −44.5 (2) | C6—C5—C10—C4 | −172.06 (16) |
O1S—S1—N2—C14 | 87.20 (18) | C15—C5—C10—C4 | 7.9 (3) |
C9—S1—N2—C14 | −159.45 (16) | O4—C4—C10—C9 | −148.27 (17) |
C14—N2—C3—C11 | −8.1 (3) | C3—C4—C10—C9 | 27.1 (2) |
S1—N2—C3—C11 | 134.06 (16) | O4—C4—C10—C5 | 25.1 (3) |
C14—N2—C3—C4 | 171.48 (18) | C3—C4—C10—C5 | −159.50 (16) |
S1—N2—C3—C4 | −46.4 (2) | N2—C3—C11—O12 | −10.9 (3) |
C11—C3—C4—O4 | −6.9 (3) | C4—C3—C11—O12 | 169.54 (17) |
N2—C3—C4—O4 | 173.54 (16) | N2—C3—C11—C21 | 165.93 (17) |
C11—C3—C4—C10 | 177.87 (16) | C4—C3—C11—C21 | −13.6 (3) |
N2—C3—C4—C10 | −1.7 (2) | C13—O12—C11—C3 | −7.2 (3) |
C10—C5—C6—C7 | 1.4 (3) | C13—O12—C11—C21 | 175.4 (2) |
C15—C5—C6—C7 | −178.59 (19) | C11—O12—C13—C14 | 42.3 (3) |
C9—N8—C7—C6 | 1.7 (3) | C3—N2—C14—C13 | 42.2 (3) |
C9—N8—C7—C16 | −177.5 (2) | S1—N2—C14—C13 | −99.3 (2) |
C5—C6—C7—N8 | −3.2 (3) | O12—C13—C14—N2 | −59.2 (3) |
C5—C6—C7—C16 | 176.0 (2) | C3—C11—C21—C26 | 135.4 (2) |
C7—N8—C9—C10 | 1.7 (3) | O12—C11—C21—C26 | −47.3 (2) |
C7—N8—C9—S1 | 176.65 (13) | C3—C11—C21—C22 | −48.3 (3) |
O2S—S1—C9—N8 | 39.05 (17) | O12—C11—C21—C22 | 128.94 (19) |
O1S—S1—C9—N8 | −92.99 (16) | C26—C21—C22—C23 | −1.1 (3) |
N2—S1—C9—N8 | 150.38 (14) | C11—C21—C22—C23 | −177.38 (18) |
O2S—S1—C9—C10 | −145.54 (14) | C21—C22—C23—C24 | 0.2 (3) |
O1S—S1—C9—C10 | 82.42 (16) | C22—C23—C24—C25 | 0.5 (4) |
N2—S1—C9—C10 | −34.22 (16) | C23—C24—C25—C26 | −0.3 (4) |
N8—C9—C10—C5 | −3.4 (3) | C22—C21—C26—C25 | 1.3 (3) |
S1—C9—C10—C5 | −178.13 (13) | C11—C21—C26—C25 | 177.69 (18) |
N8—C9—C10—C4 | 170.45 (17) | C24—C25—C26—C21 | −0.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H61···O4i | 0.86 (3) | 2.52 (3) | 3.136 (3) | 129 (2) |
C13—H132···O2Sii | 1.11 (4) | 2.42 (3) | 3.207 (3) | 126 (2) |
C23—H231···O2Siii | 0.94 (3) | 2.49 (3) | 3.426 (3) | 171 (3) |
Symmetry codes: (i) −x, y−1/2, −z; (ii) −x+1, y+1/2, −z+1; (iii) x, y, z−1. |
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