Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022816/ya6251sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022816/ya6251Isup2.hkl |
CCDC reference: 282709
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.055
- wR factor = 0.152
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - O1 .. 9.47 su
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C15 .. 5.41 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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.
C16H18N2O2S | F(000) = 640.00 |
Mr = 302.39 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 9315 reflections |
a = 17.1543 (4) Å | θ = 1.2–27.5° |
b = 8.3835 (2) Å | µ = 0.22 mm−1 |
c = 10.9679 (3) Å | T = 295 K |
β = 105.976 (1)° | Prism, yellow |
V = 1516.41 (6) Å3 | 0.30 × 0.22 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 1718 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.054 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→22 |
Tmin = 0.911, Tmax = 0.957 | k = −10→10 |
9646 measured reflections | l = −14→13 |
3458 independent reflections |
Refinement on F2 | w = 1/[0.0012Fo2 + 1.0σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.055 | (Δ/σ)max < 0.001 |
wR(F2) = 0.152 | Δρmax = 0.48 e Å−3 |
S = 1.00 | Δρmin = −0.39 e Å−3 |
3176 reflections | Extinction correction: Larson (1970), equation 22 |
191 parameters | Extinction coefficient: 88.0 (23) |
H-atom parameters constrained |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
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 | 0.20643 (4) | 0.34121 (9) | 0.71036 (7) | 0.0720 (3) | |
O1 | 0.1752 (1) | 0.1925 (2) | 0.6523 (2) | 0.0884 (8) | |
O2 | 0.2055 (1) | 0.3699 (3) | 0.8381 (2) | 0.0942 (8) | |
N1 | 0.3005 (1) | 0.3726 (3) | 0.7073 (2) | 0.0651 (7) | |
N2 | 0.6432 (1) | 0.3441 (3) | 0.5808 (2) | 0.0640 (7) | |
C1 | 0.0369 (2) | 0.8799 (4) | 0.3781 (3) | 0.091 (1) | |
C2 | 0.0796 (1) | 0.7466 (4) | 0.4614 (3) | 0.0651 (9) | |
C3 | 0.0771 (2) | 0.5939 (4) | 0.4148 (3) | 0.075 (1) | |
C4 | 0.1149 (2) | 0.4680 (4) | 0.4901 (3) | 0.073 (1) | |
C5 | 0.1552 (1) | 0.4969 (3) | 0.6142 (2) | 0.0567 (8) | |
C6 | 0.1593 (2) | 0.6488 (4) | 0.6620 (2) | 0.0657 (9) | |
C7 | 0.1221 (2) | 0.7738 (3) | 0.5861 (3) | 0.0662 (9) | |
C8 | 0.3274 (2) | 0.2888 (3) | 0.6290 (3) | 0.0605 (8) | |
C9 | 0.4080 (1) | 0.3053 (3) | 0.6171 (2) | 0.0549 (7) | |
C10 | 0.4627 (1) | 0.4146 (3) | 0.6885 (2) | 0.0585 (8) | |
C11 | 0.5396 (1) | 0.4293 (3) | 0.6769 (2) | 0.0559 (7) | |
C12 | 0.5666 (1) | 0.3306 (3) | 0.5915 (2) | 0.0536 (7) | |
C13 | 0.5112 (1) | 0.2213 (3) | 0.5199 (2) | 0.0592 (8) | |
C14 | 0.4342 (1) | 0.2098 (3) | 0.5316 (2) | 0.0591 (8) | |
C15 | 0.6705 (2) | 0.2481 (4) | 0.4909 (3) | 0.088 (1) | |
C16 | 0.6990 (2) | 0.4582 (3) | 0.6545 (3) | 0.0748 (9) | |
H1 | −0.0179 | 0.8862 | 0.3837 | 0.111* | |
H2 | 0.0643 | 0.9786 | 0.4063 | 0.111* | |
H3 | 0.0364 | 0.8599 | 0.2917 | 0.111* | |
H4 | 0.0476 | 0.5731 | 0.3262 | 0.087* | |
H5 | 0.1138 | 0.3603 | 0.4549 | 0.087* | |
H6 | 0.1893 | 0.6688 | 0.7505 | 0.077* | |
H7 | 0.1252 | 0.8821 | 0.6207 | 0.080* | |
H8 | 0.2912 | 0.2107 | 0.5752 | 0.071* | |
H9 | 0.4459 | 0.4827 | 0.7493 | 0.069* | |
H10 | 0.5766 | 0.5086 | 0.7277 | 0.065* | |
H11 | 0.5282 | 0.1510 | 0.4606 | 0.071* | |
H12 | 0.3966 | 0.1330 | 0.4788 | 0.070* | |
H13 | 0.6933 | 0.1505 | 0.5310 | 0.109* | |
H14 | 0.7107 | 0.3055 | 0.4627 | 0.109* | |
H15 | 0.6254 | 0.2243 | 0.4192 | 0.109* | |
H16 | 0.6701 | 0.5524 | 0.6663 | 0.089* | |
H17 | 0.7256 | 0.4128 | 0.7356 | 0.089* | |
H18 | 0.7387 | 0.4855 | 0.6110 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0667 (5) | 0.0704 (6) | 0.0837 (6) | 0.0126 (4) | 0.0285 (4) | 0.0197 (4) |
O1 | 0.072 (1) | 0.058 (1) | 0.139 (2) | −0.002 (1) | 0.036 (1) | 0.010 (1) |
O2 | 0.100 (2) | 0.115 (2) | 0.077 (1) | 0.035 (1) | 0.040 (1) | 0.038 (1) |
N1 | 0.056 (1) | 0.064 (2) | 0.075 (1) | 0.008 (1) | 0.017 (1) | 0.007 (1) |
N2 | 0.062 (1) | 0.061 (1) | 0.072 (1) | −0.007 (1) | 0.023 (1) | −0.006 (1) |
C1 | 0.075 (2) | 0.106 (3) | 0.094 (2) | 0.029 (2) | 0.030 (2) | 0.032 (2) |
C2 | 0.054 (2) | 0.073 (2) | 0.071 (2) | 0.010 (1) | 0.022 (1) | 0.014 (2) |
C3 | 0.072 (2) | 0.085 (2) | 0.060 (2) | −0.004 (2) | 0.004 (1) | −0.002 (2) |
C4 | 0.079 (2) | 0.061 (2) | 0.076 (2) | −0.003 (1) | 0.016 (2) | −0.010 (2) |
C5 | 0.055 (1) | 0.059 (2) | 0.058 (2) | 0.002 (1) | 0.019 (1) | 0.003 (1) |
C6 | 0.068 (2) | 0.071 (2) | 0.053 (2) | 0.004 (1) | 0.009 (1) | −0.004 (1) |
C7 | 0.065 (2) | 0.059 (2) | 0.076 (2) | 0.009 (1) | 0.022 (1) | 0.001 (2) |
C8 | 0.065 (2) | 0.053 (2) | 0.061 (2) | 0.006 (1) | 0.012 (1) | 0.009 (1) |
C9 | 0.057 (1) | 0.049 (2) | 0.058 (2) | 0.004 (1) | 0.015 (1) | 0.010 (1) |
C10 | 0.066 (2) | 0.054 (2) | 0.055 (1) | 0.010 (1) | 0.014 (1) | 0.002 (1) |
C11 | 0.058 (2) | 0.049 (2) | 0.054 (1) | −0.001 (1) | 0.006 (1) | −0.004 (1) |
C12 | 0.057 (1) | 0.048 (1) | 0.054 (1) | 0.001 (1) | 0.012 (1) | 0.006 (1) |
C13 | 0.068 (2) | 0.050 (2) | 0.060 (2) | −0.003 (1) | 0.018 (1) | −0.008 (1) |
C14 | 0.064 (2) | 0.049 (2) | 0.063 (2) | −0.007 (1) | 0.014 (1) | −0.001 (1) |
C15 | 0.071 (2) | 0.092 (2) | 0.109 (2) | −0.006 (2) | 0.040 (2) | −0.016 (2) |
C16 | 0.060 (2) | 0.072 (2) | 0.088 (2) | −0.009 (1) | 0.013 (1) | −0.000 (2) |
S1—O1 | 1.435 (2) | C12—C13 | 1.396 (3) |
S1—O2 | 1.426 (2) | C13—C14 | 1.365 (4) |
S1—N1 | 1.645 (2) | C1—H1 | 0.960 |
S1—C5 | 1.755 (2) | C1—H2 | 0.960 |
N1—C8 | 1.289 (4) | C1—H3 | 0.960 |
N2—C12 | 1.355 (4) | C3—H4 | 0.980 |
N2—C15 | 1.447 (4) | C4—H5 | 0.980 |
N2—C16 | 1.435 (3) | C6—H6 | 0.980 |
C1—C2 | 1.501 (4) | C7—H7 | 0.980 |
C2—C3 | 1.375 (4) | C8—H8 | 0.980 |
C2—C7 | 1.381 (4) | C10—H9 | 0.980 |
C3—C4 | 1.386 (4) | C11—H10 | 0.980 |
C4—C5 | 1.368 (3) | C13—H11 | 0.980 |
C5—C6 | 1.371 (4) | C14—H12 | 0.980 |
C6—C7 | 1.380 (4) | C15—H13 | 0.960 |
C8—C9 | 1.432 (4) | C15—H14 | 0.960 |
C9—C10 | 1.388 (3) | C15—H15 | 0.960 |
C9—C14 | 1.398 (4) | C16—H16 | 0.960 |
C10—C11 | 1.364 (4) | C16—H17 | 0.960 |
C11—C12 | 1.420 (4) | C16—H18 | 0.960 |
S1···C4 | 2.710 (3) | C3···C5 | 2.372 (4) |
S1···C6 | 2.711 (3) | C3···C6 | 2.729 (4) |
S1···C8 | 2.513 (3) | C3···C7 | 2.367 (4) |
O1···O2 | 2.460 (3) | C4···C6 | 2.375 (4) |
O1···N1 | 2.559 (3) | C4···C7 | 2.761 (4) |
O1···C4 | 2.926 (3) | C5···C7 | 2.389 (4) |
O1···C5 | 2.594 (3) | C5···C8 | 3.396 (4) |
O1···C8 | 2.810 (4) | C6···C1iv | 3.581 (5) |
O1···C16i | 3.238 (3) | C8···O2v | 3.557 (3) |
O2···N1 | 2.450 (3) | C8···C10 | 2.469 (4) |
O2···C5 | 2.596 (3) | C8···C14 | 2.452 (4) |
O2···C6 | 2.997 (3) | C9···C11 | 2.405 (3) |
O2···C8 | 3.568 (4) | C9···C12 | 2.818 (4) |
O2···C8ii | 3.557 (3) | C9···C13 | 2.409 (4) |
N1···C4 | 3.504 (3) | C10···C12 | 2.418 (4) |
N1···C5 | 2.635 (3) | C10···C13 | 2.753 (4) |
N1···C6 | 3.289 (4) | C10···C14 | 2.384 (3) |
N1···C9 | 2.388 (4) | C11···C13 | 2.405 (3) |
N1···C10 | 2.868 (3) | C11···C14 | 2.758 (3) |
N2···C11 | 2.411 (4) | C11···C16 | 2.823 (4) |
N2···C13 | 2.408 (3) | C12···C14 | 2.407 (3) |
C1···C3 | 2.497 (5) | C12···C15 | 2.440 (5) |
C1···C6iii | 3.581 (5) | C12···C16 | 2.432 (4) |
C1···C7 | 2.510 (4) | C13···C15 | 2.845 (4) |
C2···C4 | 2.411 (4) | C15···C16 | 2.466 (4) |
C2···C5 | 2.770 (4) | C16···O1vi | 3.238 (3) |
C2···C6 | 2.393 (4) | ||
O2—S1—O1 | 118.6 (1) | N2—C15—H15 | 109.6 |
N1—S1—O1 | 112.2 (1) | N2—C16—H16 | 109.6 |
C5—S1—O1 | 108.4 (1) | N2—C16—H17 | 109.3 |
N1—S1—O2 | 105.6 (1) | N2—C16—H18 | 109.5 |
C5—S1—O2 | 109.0 (1) | H1—C1—C2 | 108.9 |
C5—S1—N1 | 101.6 (1) | H2—C1—C2 | 109.3 |
S1—N1—C8 | 117.3 (2) | H3—C1—C2 | 109.9 |
S1—C5—C4 | 119.9 (2) | H2—C1—H1 | 109.5 |
S1—C5—C6 | 119.8 (2) | H3—C1—H1 | 109.4 |
N1—C8—C9 | 122.6 (2) | H3—C1—H2 | 109.8 |
N2—C12—C11 | 120.6 (2) | C2—C3—H4 | 119.2 |
N2—C12—C13 | 122.2 (2) | C2—C7—H7 | 119.6 |
C15—N2—C12 | 121.0 (2) | C3—C4—H5 | 120.7 |
C16—N2—C12 | 121.3 (2) | H4—C3—C4 | 119.0 |
C16—N2—C15 | 117.6 (2) | H5—C4—C5 | 120.3 |
C1—C2—C3 | 120.5 (2) | C5—C6—H6 | 119.6 |
C1—C2—C7 | 121.1 (3) | H6—C6—C7 | 119.8 |
C2—C3—C4 | 121.7 (3) | C6—C7—H7 | 120.2 |
C7—C2—C3 | 118.4 (3) | H8—C8—C9 | 118.6 |
C2—C7—C6 | 120.2 (3) | C9—C10—H9 | 119.3 |
C3—C4—C5 | 118.9 (3) | C9—C14—H12 | 119.5 |
C4—C5—C6 | 120.2 (2) | H9—C10—C11 | 118.9 |
C5—C6—C7 | 120.5 (2) | C10—C11—H10 | 120.0 |
C8—C9—C10 | 122.2 (2) | H10—C11—C12 | 119.5 |
C8—C9—C14 | 120.1 (2) | C12—C13—H11 | 119.1 |
C9—C10—C11 | 121.8 (2) | H11—C13—C14 | 119.6 |
C14—C9—C10 | 117.7 (2) | C13—C14—H12 | 119.2 |
C9—C14—C13 | 121.3 (2) | H14—C15—H13 | 109.6 |
C10—C11—C12 | 120.5 (2) | H15—C15—H13 | 109.5 |
C11—C12—C13 | 117.2 (2) | H15—C15—H14 | 109.2 |
C12—C13—C14 | 121.4 (3) | H17—C16—H16 | 109.5 |
N1—C8—H8 | 118.8 | H18—C16—H16 | 109.5 |
N2—C15—H13 | 109.2 | H18—C16—H17 | 109.5 |
N2—C15—H14 | 109.7 | ||
O1—S1—N1—C8 | 17.4 (2) | C2—C3—C4—C5 | 0.6 (5) |
O2—S1—N1—C8 | 148.0 (2) | C3—C4—C5—S1 | −177.9 (2) |
C5—S1—N1—C8 | −98.2 (2) | C3—C4—C5—C6 | −1.4 (4) |
O1—S1—C5—C4 | −19.1 (3) | S1—C5—C6—C7 | 177.4 (3) |
O1—S1—C5—C6 | 164.4 (2) | C4—C5—C6—C7 | 0.9 (4) |
O2—S1—C5—C4 | −149.5 (2) | C5—C6—C7—C2 | 0.5 (5) |
O2—S1—C5—C6 | 34.0 (3) | N1—C8—C9—C10 | −0.7 (4) |
N1—S1—C5—C4 | 99.3 (2) | N1—C8—C9—C14 | 179.2 (2) |
N1—S1—C5—C6 | −77.2 (2) | C8—C9—C10—C11 | 179.8 (2) |
S1—N1—C8—C9 | 179.8 (2) | C14—C9—C10—C11 | −0.2 (4) |
C15—N2—C12—C11 | −177.8 (2) | C8—C9—C14—C13 | −178.8 (2) |
C15—N2—C12—C13 | 1.9 (4) | C10—C9—C14—C13 | 1.1 (4) |
C16—N2—C12—C11 | −0.3 (3) | C9—C10—C11—C12 | −0.8 (4) |
C16—N2—C12—C13 | 179.5 (2) | C10—C11—C12—N2 | −179.4 (2) |
C1—C2—C3—C4 | −179.0 (3) | C10—C11—C12—C13 | 0.9 (3) |
C7—C2—C3—C4 | 0.8 (5) | N2—C12—C13—C14 | −179.7 (2) |
C1—C2—C7—C6 | 178.4 (3) | C11—C12—C13—C14 | 0.0 (3) |
C3—C2—C7—C6 | −1.4 (4) | C12—C13—C14—C9 | −1.0 (4) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2; (v) x, −y+1/2, z−1/2; (vi) −x+1, y+1/2, −z+3/2. |
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