Refinement of the title structure, C15H25NO2S, using low-temperature single-crystal X-ray data, confirms the results from powder diffraction data [Tremayne, MacLean, Tang & Glidewell (1999). Acta Cryst. B55, 1068-1074]. The S=O distances are 1.4252 (18) and 1.4301 (16) Å, and the S-N distance is 1.601 (2) Å.
Supporting information
CCDC reference: 227912
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.053
- wR factor = 0.136
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.58 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.04 Ratio
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
0 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
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: COLLECT (Nonius 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare, et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
2,4,6-triisopropylbenzenesulfonamide
top
Crystal data top
C15H25NO2S | F(000) = 616 |
Mr = 283.42 | Dx = 1.205 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3779 reflections |
a = 16.963 (5) Å | θ = 2.5–27.5° |
b = 8.108 (2) Å | µ = 0.21 mm−1 |
c = 11.752 (3) Å | T = 100 K |
β = 104.836 (11)° | Rhombic plate, colorless |
V = 1562.4 (7) Å3 | 0.20 × 0.20 × 0.05 mm |
Z = 4 | |
Data collection top
KappaCCD (with Oxford Cryostream) diffractometer | 3590 independent reflections |
Radiation source: fine-focus sealed tube | 2729 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans with κ offsets | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (HKL Scalepack; Otwinowski & Minor, 1997) | h = −22→21 |
Tmin = 0.931, Tmax = 0.990 | k = −10→10 |
26071 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0522P)2 + 1.3564P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3590 reflections | Δρmax = 0.46 e Å−3 |
185 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0046 (12) |
Special details top
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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.58713 (3) | 0.38464 (7) | 0.66892 (4) | 0.02570 (17) | |
O1 | 0.57172 (9) | 0.3433 (2) | 0.54689 (13) | 0.0331 (4) | |
O2 | 0.58091 (11) | 0.2581 (3) | 0.75038 (18) | 0.0629 (7) | |
N1 | 0.52246 (12) | 0.5232 (3) | 0.68063 (19) | 0.0413 (6) | |
H1N | 0.4982 (18) | 0.572 (4) | 0.619 (3) | 0.050* | |
H2N | 0.5117 (17) | 0.537 (4) | 0.746 (3) | 0.050* | |
C1 | 0.68668 (11) | 0.4772 (2) | 0.71205 (16) | 0.0183 (4) | |
C2 | 0.69896 (11) | 0.6238 (2) | 0.65384 (16) | 0.0182 (4) | |
C3 | 0.77509 (12) | 0.6996 (2) | 0.68878 (16) | 0.0200 (4) | |
H3 | 0.7838 | 0.7988 | 0.6507 | 0.024* | |
C4 | 0.83871 (12) | 0.6365 (2) | 0.77672 (16) | 0.0204 (4) | |
C5 | 0.82520 (12) | 0.4890 (3) | 0.82838 (17) | 0.0230 (4) | |
H5 | 0.8688 | 0.4425 | 0.8869 | 0.028* | |
C6 | 0.75069 (12) | 0.4050 (2) | 0.79881 (17) | 0.0215 (4) | |
C7 | 0.63617 (12) | 0.7071 (2) | 0.55345 (17) | 0.0221 (4) | |
H7 | 0.5861 | 0.6367 | 0.5344 | 0.027* | |
C8 | 0.61224 (15) | 0.8770 (3) | 0.5910 (2) | 0.0331 (5) | |
H8A | 0.5917 | 0.8653 | 0.6613 | 0.050* | |
H8B | 0.5696 | 0.9249 | 0.5270 | 0.050* | |
H8C | 0.6601 | 0.9494 | 0.6087 | 0.050* | |
C9 | 0.66742 (14) | 0.7191 (3) | 0.44239 (18) | 0.0314 (5) | |
H9A | 0.7163 | 0.7885 | 0.4584 | 0.047* | |
H9B | 0.6251 | 0.7678 | 0.3784 | 0.047* | |
H9C | 0.6809 | 0.6085 | 0.4193 | 0.047* | |
C10 | 0.92032 (12) | 0.7237 (3) | 0.81284 (18) | 0.0248 (4) | |
H10 | 0.9143 | 0.8323 | 0.7713 | 0.030* | |
C11 | 0.98642 (13) | 0.6262 (3) | 0.7745 (2) | 0.0333 (5) | |
H11A | 0.9940 | 0.5190 | 0.8144 | 0.050* | |
H11B | 1.0378 | 0.6879 | 0.7955 | 0.050* | |
H11C | 0.9698 | 0.6092 | 0.6891 | 0.050* | |
C12 | 0.94656 (14) | 0.7581 (3) | 0.94503 (19) | 0.0331 (5) | |
H12A | 0.9026 | 0.8158 | 0.9689 | 0.050* | |
H12B | 0.9957 | 0.8268 | 0.9630 | 0.050* | |
H12C | 0.9582 | 0.6535 | 0.9880 | 0.050* | |
C13 | 0.74928 (13) | 0.2402 (3) | 0.8614 (2) | 0.0323 (5) | |
H13 | 0.6936 | 0.1915 | 0.8318 | 0.039* | |
C14 | 0.81042 (18) | 0.1206 (3) | 0.8323 (2) | 0.0436 (7) | |
H14A | 0.8659 | 0.1574 | 0.8705 | 0.065* | |
H14B | 0.8031 | 0.1173 | 0.7468 | 0.065* | |
H14C | 0.8017 | 0.0102 | 0.8607 | 0.065* | |
C15 | 0.7651 (2) | 0.2611 (4) | 0.9923 (3) | 0.0649 (10) | |
H15A | 0.8176 | 0.3168 | 1.0227 | 0.097* | |
H15B | 0.7666 | 0.1526 | 1.0296 | 0.097* | |
H15C | 0.7215 | 0.3277 | 1.0101 | 0.097* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0230 (3) | 0.0255 (3) | 0.0259 (3) | −0.0052 (2) | 0.00129 (19) | 0.0051 (2) |
O1 | 0.0322 (8) | 0.0274 (8) | 0.0329 (8) | 0.0052 (7) | −0.0041 (6) | −0.0104 (7) |
O2 | 0.0353 (10) | 0.0725 (15) | 0.0672 (13) | −0.0246 (10) | −0.0121 (9) | 0.0487 (12) |
N1 | 0.0255 (10) | 0.0744 (17) | 0.0259 (10) | 0.0128 (11) | 0.0100 (8) | −0.0030 (11) |
C1 | 0.0196 (9) | 0.0178 (9) | 0.0184 (9) | −0.0011 (8) | 0.0061 (7) | −0.0025 (7) |
C2 | 0.0206 (9) | 0.0172 (9) | 0.0171 (9) | 0.0024 (8) | 0.0054 (7) | 0.0002 (7) |
C3 | 0.0248 (10) | 0.0147 (9) | 0.0211 (9) | 0.0012 (8) | 0.0069 (8) | 0.0021 (7) |
C4 | 0.0223 (10) | 0.0182 (10) | 0.0208 (9) | 0.0005 (8) | 0.0059 (7) | −0.0006 (7) |
C5 | 0.0198 (9) | 0.0221 (10) | 0.0252 (10) | 0.0022 (8) | 0.0022 (8) | 0.0058 (8) |
C6 | 0.0217 (10) | 0.0180 (10) | 0.0254 (10) | 0.0027 (8) | 0.0073 (8) | 0.0036 (8) |
C7 | 0.0220 (10) | 0.0191 (10) | 0.0240 (10) | 0.0031 (8) | 0.0036 (8) | 0.0039 (8) |
C8 | 0.0342 (12) | 0.0247 (12) | 0.0387 (12) | 0.0101 (10) | 0.0059 (10) | 0.0034 (10) |
C9 | 0.0317 (12) | 0.0381 (13) | 0.0232 (10) | 0.0057 (10) | 0.0049 (9) | 0.0080 (9) |
C10 | 0.0229 (10) | 0.0205 (10) | 0.0285 (10) | −0.0019 (8) | 0.0020 (8) | 0.0046 (8) |
C11 | 0.0243 (11) | 0.0384 (14) | 0.0380 (12) | −0.0022 (10) | 0.0094 (9) | 0.0040 (10) |
C12 | 0.0290 (12) | 0.0305 (12) | 0.0346 (12) | −0.0032 (10) | −0.0011 (9) | −0.0031 (10) |
C13 | 0.0221 (11) | 0.0249 (12) | 0.0477 (13) | −0.0016 (9) | 0.0050 (9) | 0.0165 (10) |
C14 | 0.0710 (19) | 0.0183 (11) | 0.0405 (14) | 0.0056 (12) | 0.0125 (13) | 0.0033 (10) |
C15 | 0.120 (3) | 0.0410 (17) | 0.0546 (18) | 0.0248 (18) | 0.0596 (19) | 0.0231 (14) |
Geometric parameters (Å, º) top
S1—O2 | 1.4252 (18) | C8—H8C | 0.98 |
S1—O1 | 1.4301 (16) | C9—H9A | 0.98 |
S1—N1 | 1.601 (2) | C9—H9B | 0.98 |
S1—C1 | 1.798 (2) | C9—H9C | 0.98 |
N1—H1N | 0.84 (3) | C10—C12 | 1.528 (3) |
N1—H2N | 0.84 (3) | C10—C11 | 1.531 (3) |
C1—C6 | 1.412 (3) | C10—H10 | 1.00 |
C1—C2 | 1.414 (3) | C11—H11A | 0.98 |
C2—C3 | 1.394 (3) | C11—H11B | 0.98 |
C2—C7 | 1.529 (3) | C11—H11C | 0.98 |
C3—C4 | 1.387 (3) | C12—H12A | 0.98 |
C3—H3 | 0.95 | C12—H12B | 0.98 |
C4—C5 | 1.386 (3) | C12—H12C | 0.98 |
C4—C10 | 1.515 (3) | C13—C15 | 1.502 (4) |
C5—C6 | 1.399 (3) | C13—C14 | 1.521 (4) |
C5—H5 | 0.95 | C13—H13 | 1.00 |
C6—C13 | 1.529 (3) | C14—H14A | 0.98 |
C7—C9 | 1.532 (3) | C14—H14B | 0.98 |
C7—C8 | 1.533 (3) | C14—H14C | 0.98 |
C7—H7 | 1.00 | C15—H15A | 0.98 |
C8—H8A | 0.98 | C15—H15B | 0.98 |
C8—H8B | 0.98 | C15—H15C | 0.98 |
| | | |
O2—S1—O1 | 118.63 (13) | H9A—C9—H9B | 109.5 |
O2—S1—N1 | 106.09 (14) | C7—C9—H9C | 109.5 |
O1—S1—N1 | 107.30 (10) | H9A—C9—H9C | 109.5 |
O2—S1—C1 | 109.66 (10) | H9B—C9—H9C | 109.5 |
O1—S1—C1 | 107.32 (9) | C4—C10—C12 | 112.17 (17) |
N1—S1—C1 | 107.33 (11) | C4—C10—C11 | 111.23 (18) |
S1—N1—H1N | 117 (2) | C12—C10—C11 | 110.41 (18) |
S1—N1—H2N | 119 (2) | C4—C10—H10 | 107.6 |
H1N—N1—H2N | 124 (3) | C12—C10—H10 | 107.6 |
C6—C1—C2 | 121.10 (18) | C11—C10—H10 | 107.6 |
C6—C1—S1 | 121.59 (15) | C10—C11—H11A | 109.5 |
C2—C1—S1 | 117.30 (14) | C10—C11—H11B | 109.5 |
C3—C2—C1 | 117.93 (17) | H11A—C11—H11B | 109.5 |
C3—C2—C7 | 116.27 (17) | C10—C11—H11C | 109.5 |
C1—C2—C7 | 125.79 (17) | H11A—C11—H11C | 109.5 |
C4—C3—C2 | 122.85 (18) | H11B—C11—H11C | 109.5 |
C4—C3—H3 | 118.6 | C10—C12—H12A | 109.5 |
C2—C3—H3 | 118.6 | C10—C12—H12B | 109.5 |
C5—C4—C3 | 117.40 (18) | H12A—C12—H12B | 109.5 |
C5—C4—C10 | 121.43 (18) | C10—C12—H12C | 109.5 |
C3—C4—C10 | 121.16 (18) | H12A—C12—H12C | 109.5 |
C4—C5—C6 | 123.45 (18) | H12B—C12—H12C | 109.5 |
C4—C5—H5 | 118.3 | C15—C13—C14 | 110.4 (2) |
C6—C5—H5 | 118.3 | C15—C13—C6 | 111.9 (2) |
C5—C6—C1 | 117.16 (18) | C14—C13—C6 | 110.66 (19) |
C5—C6—C13 | 115.50 (17) | C15—C13—H13 | 107.9 |
C1—C6—C13 | 127.28 (18) | C14—C13—H13 | 107.9 |
C2—C7—C9 | 111.14 (16) | C6—C13—H13 | 107.9 |
C2—C7—C8 | 110.99 (17) | C13—C14—H14A | 109.5 |
C9—C7—C8 | 111.28 (18) | C13—C14—H14B | 109.5 |
C2—C7—H7 | 107.8 | H14A—C14—H14B | 109.5 |
C9—C7—H7 | 107.8 | C13—C14—H14C | 109.5 |
C8—C7—H7 | 107.8 | H14A—C14—H14C | 109.5 |
C7—C8—H8A | 109.5 | H14B—C14—H14C | 109.5 |
C7—C8—H8B | 109.5 | C13—C15—H15A | 109.5 |
H8A—C8—H8B | 109.5 | C13—C15—H15B | 109.5 |
C7—C8—H8C | 109.5 | H15A—C15—H15B | 109.5 |
H8A—C8—H8C | 109.5 | C13—C15—H15C | 109.5 |
H8B—C8—H8C | 109.5 | H15A—C15—H15C | 109.5 |
C7—C9—H9A | 109.5 | H15B—C15—H15C | 109.5 |
C7—C9—H9B | 109.5 | | |
| | | |
O2—S1—C1—C6 | 12.2 (2) | C4—C5—C6—C13 | 177.2 (2) |
O1—S1—C1—C6 | −117.89 (17) | C2—C1—C6—C5 | 3.0 (3) |
N1—S1—C1—C6 | 127.05 (18) | S1—C1—C6—C5 | −178.30 (14) |
O2—S1—C1—C2 | −169.01 (17) | C2—C1—C6—C13 | −174.21 (19) |
O1—S1—C1—C2 | 60.87 (17) | S1—C1—C6—C13 | 4.5 (3) |
N1—S1—C1—C2 | −54.19 (17) | C3—C2—C7—C9 | 58.8 (2) |
C6—C1—C2—C3 | −3.1 (3) | C1—C2—C7—C9 | −120.2 (2) |
S1—C1—C2—C3 | 178.13 (14) | C3—C2—C7—C8 | −65.6 (2) |
C6—C1—C2—C7 | 175.89 (18) | C1—C2—C7—C8 | 115.4 (2) |
S1—C1—C2—C7 | −2.9 (3) | C5—C4—C10—C12 | −55.6 (3) |
C1—C2—C3—C4 | 0.6 (3) | C3—C4—C10—C12 | 125.8 (2) |
C7—C2—C3—C4 | −178.50 (18) | C5—C4—C10—C11 | 68.7 (2) |
C2—C3—C4—C5 | 1.9 (3) | C3—C4—C10—C11 | −110.0 (2) |
C2—C3—C4—C10 | −179.41 (18) | C5—C6—C13—C15 | 62.7 (3) |
C3—C4—C5—C6 | −2.0 (3) | C1—C6—C13—C15 | −120.0 (3) |
C10—C4—C5—C6 | 179.30 (19) | C5—C6—C13—C14 | −60.9 (3) |
C4—C5—C6—C1 | −0.4 (3) | C1—C6—C13—C14 | 116.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.84 (3) | 2.12 (3) | 2.947 (3) | 170 (3) |
N1—H2N···O2ii | 0.84 (3) | 2.39 (3) | 2.844 (3) | 114 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2. |