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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026382/lh6141sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026382/lh6141IIsup2.hkl
Contains datablock II

CCDC reference: 227912

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.136
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

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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

Computing details top

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
C15H25NO2SF(000) = 616
Mr = 283.42Dx = 1.205 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3779 reflections
a = 16.963 (5) Åθ = 2.5–27.5°
b = 8.108 (2) ŵ = 0.21 mm1
c = 11.752 (3) ÅT = 100 K
β = 104.836 (11)°Rhombic plate, colorless
V = 1562.4 (7) Å30.20 × 0.20 × 0.05 mm
Z = 4
Data collection top
KappaCCD (with Oxford Cryostream)
diffractometer
3590 independent reflections
Radiation source: fine-focus sealed tube2729 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scans with κ offsetsθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(HKL Scalepack; Otwinowski & Minor, 1997)
h = 2221
Tmin = 0.931, Tmax = 0.990k = 1010
26071 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H 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 reflectionsΔρmax = 0.46 e Å3
185 parametersΔρmin = 0.42 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
S10.58713 (3)0.38464 (7)0.66892 (4)0.02570 (17)
O10.57172 (9)0.3433 (2)0.54689 (13)0.0331 (4)
O20.58091 (11)0.2581 (3)0.75038 (18)0.0629 (7)
N10.52246 (12)0.5232 (3)0.68063 (19)0.0413 (6)
H1N0.4982 (18)0.572 (4)0.619 (3)0.050*
H2N0.5117 (17)0.537 (4)0.746 (3)0.050*
C10.68668 (11)0.4772 (2)0.71205 (16)0.0183 (4)
C20.69896 (11)0.6238 (2)0.65384 (16)0.0182 (4)
C30.77509 (12)0.6996 (2)0.68878 (16)0.0200 (4)
H30.78380.79880.65070.024*
C40.83871 (12)0.6365 (2)0.77672 (16)0.0204 (4)
C50.82520 (12)0.4890 (3)0.82838 (17)0.0230 (4)
H50.86880.44250.88690.028*
C60.75069 (12)0.4050 (2)0.79881 (17)0.0215 (4)
C70.63617 (12)0.7071 (2)0.55345 (17)0.0221 (4)
H70.58610.63670.53440.027*
C80.61224 (15)0.8770 (3)0.5910 (2)0.0331 (5)
H8A0.59170.86530.66130.050*
H8B0.56960.92490.52700.050*
H8C0.66010.94940.60870.050*
C90.66742 (14)0.7191 (3)0.44239 (18)0.0314 (5)
H9A0.71630.78850.45840.047*
H9B0.62510.76780.37840.047*
H9C0.68090.60850.41930.047*
C100.92032 (12)0.7237 (3)0.81284 (18)0.0248 (4)
H100.91430.83230.77130.030*
C110.98642 (13)0.6262 (3)0.7745 (2)0.0333 (5)
H11A0.99400.51900.81440.050*
H11B1.03780.68790.79550.050*
H11C0.96980.60920.68910.050*
C120.94656 (14)0.7581 (3)0.94503 (19)0.0331 (5)
H12A0.90260.81580.96890.050*
H12B0.99570.82680.96300.050*
H12C0.95820.65350.98800.050*
C130.74928 (13)0.2402 (3)0.8614 (2)0.0323 (5)
H130.69360.19150.83180.039*
C140.81042 (18)0.1206 (3)0.8323 (2)0.0436 (7)
H14A0.86590.15740.87050.065*
H14B0.80310.11730.74680.065*
H14C0.80170.01020.86070.065*
C150.7651 (2)0.2611 (4)0.9923 (3)0.0649 (10)
H15A0.81760.31681.02270.097*
H15B0.76660.15261.02960.097*
H15C0.72150.32771.01010.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0230 (3)0.0255 (3)0.0259 (3)0.0052 (2)0.00129 (19)0.0051 (2)
O10.0322 (8)0.0274 (8)0.0329 (8)0.0052 (7)0.0041 (6)0.0104 (7)
O20.0353 (10)0.0725 (15)0.0672 (13)0.0246 (10)0.0121 (9)0.0487 (12)
N10.0255 (10)0.0744 (17)0.0259 (10)0.0128 (11)0.0100 (8)0.0030 (11)
C10.0196 (9)0.0178 (9)0.0184 (9)0.0011 (8)0.0061 (7)0.0025 (7)
C20.0206 (9)0.0172 (9)0.0171 (9)0.0024 (8)0.0054 (7)0.0002 (7)
C30.0248 (10)0.0147 (9)0.0211 (9)0.0012 (8)0.0069 (8)0.0021 (7)
C40.0223 (10)0.0182 (10)0.0208 (9)0.0005 (8)0.0059 (7)0.0006 (7)
C50.0198 (9)0.0221 (10)0.0252 (10)0.0022 (8)0.0022 (8)0.0058 (8)
C60.0217 (10)0.0180 (10)0.0254 (10)0.0027 (8)0.0073 (8)0.0036 (8)
C70.0220 (10)0.0191 (10)0.0240 (10)0.0031 (8)0.0036 (8)0.0039 (8)
C80.0342 (12)0.0247 (12)0.0387 (12)0.0101 (10)0.0059 (10)0.0034 (10)
C90.0317 (12)0.0381 (13)0.0232 (10)0.0057 (10)0.0049 (9)0.0080 (9)
C100.0229 (10)0.0205 (10)0.0285 (10)0.0019 (8)0.0020 (8)0.0046 (8)
C110.0243 (11)0.0384 (14)0.0380 (12)0.0022 (10)0.0094 (9)0.0040 (10)
C120.0290 (12)0.0305 (12)0.0346 (12)0.0032 (10)0.0011 (9)0.0031 (10)
C130.0221 (11)0.0249 (12)0.0477 (13)0.0016 (9)0.0050 (9)0.0165 (10)
C140.0710 (19)0.0183 (11)0.0405 (14)0.0056 (12)0.0125 (13)0.0033 (10)
C150.120 (3)0.0410 (17)0.0546 (18)0.0248 (18)0.0596 (19)0.0231 (14)
Geometric parameters (Å, º) top
S1—O21.4252 (18)C8—H8C0.98
S1—O11.4301 (16)C9—H9A0.98
S1—N11.601 (2)C9—H9B0.98
S1—C11.798 (2)C9—H9C0.98
N1—H1N0.84 (3)C10—C121.528 (3)
N1—H2N0.84 (3)C10—C111.531 (3)
C1—C61.412 (3)C10—H101.00
C1—C21.414 (3)C11—H11A0.98
C2—C31.394 (3)C11—H11B0.98
C2—C71.529 (3)C11—H11C0.98
C3—C41.387 (3)C12—H12A0.98
C3—H30.95C12—H12B0.98
C4—C51.386 (3)C12—H12C0.98
C4—C101.515 (3)C13—C151.502 (4)
C5—C61.399 (3)C13—C141.521 (4)
C5—H50.95C13—H131.00
C6—C131.529 (3)C14—H14A0.98
C7—C91.532 (3)C14—H14B0.98
C7—C81.533 (3)C14—H14C0.98
C7—H71.00C15—H15A0.98
C8—H8A0.98C15—H15B0.98
C8—H8B0.98C15—H15C0.98
O2—S1—O1118.63 (13)H9A—C9—H9B109.5
O2—S1—N1106.09 (14)C7—C9—H9C109.5
O1—S1—N1107.30 (10)H9A—C9—H9C109.5
O2—S1—C1109.66 (10)H9B—C9—H9C109.5
O1—S1—C1107.32 (9)C4—C10—C12112.17 (17)
N1—S1—C1107.33 (11)C4—C10—C11111.23 (18)
S1—N1—H1N117 (2)C12—C10—C11110.41 (18)
S1—N1—H2N119 (2)C4—C10—H10107.6
H1N—N1—H2N124 (3)C12—C10—H10107.6
C6—C1—C2121.10 (18)C11—C10—H10107.6
C6—C1—S1121.59 (15)C10—C11—H11A109.5
C2—C1—S1117.30 (14)C10—C11—H11B109.5
C3—C2—C1117.93 (17)H11A—C11—H11B109.5
C3—C2—C7116.27 (17)C10—C11—H11C109.5
C1—C2—C7125.79 (17)H11A—C11—H11C109.5
C4—C3—C2122.85 (18)H11B—C11—H11C109.5
C4—C3—H3118.6C10—C12—H12A109.5
C2—C3—H3118.6C10—C12—H12B109.5
C5—C4—C3117.40 (18)H12A—C12—H12B109.5
C5—C4—C10121.43 (18)C10—C12—H12C109.5
C3—C4—C10121.16 (18)H12A—C12—H12C109.5
C4—C5—C6123.45 (18)H12B—C12—H12C109.5
C4—C5—H5118.3C15—C13—C14110.4 (2)
C6—C5—H5118.3C15—C13—C6111.9 (2)
C5—C6—C1117.16 (18)C14—C13—C6110.66 (19)
C5—C6—C13115.50 (17)C15—C13—H13107.9
C1—C6—C13127.28 (18)C14—C13—H13107.9
C2—C7—C9111.14 (16)C6—C13—H13107.9
C2—C7—C8110.99 (17)C13—C14—H14A109.5
C9—C7—C8111.28 (18)C13—C14—H14B109.5
C2—C7—H7107.8H14A—C14—H14B109.5
C9—C7—H7107.8C13—C14—H14C109.5
C8—C7—H7107.8H14A—C14—H14C109.5
C7—C8—H8A109.5H14B—C14—H14C109.5
C7—C8—H8B109.5C13—C15—H15A109.5
H8A—C8—H8B109.5C13—C15—H15B109.5
C7—C8—H8C109.5H15A—C15—H15B109.5
H8A—C8—H8C109.5C13—C15—H15C109.5
H8B—C8—H8C109.5H15A—C15—H15C109.5
C7—C9—H9A109.5H15B—C15—H15C109.5
C7—C9—H9B109.5
O2—S1—C1—C612.2 (2)C4—C5—C6—C13177.2 (2)
O1—S1—C1—C6117.89 (17)C2—C1—C6—C53.0 (3)
N1—S1—C1—C6127.05 (18)S1—C1—C6—C5178.30 (14)
O2—S1—C1—C2169.01 (17)C2—C1—C6—C13174.21 (19)
O1—S1—C1—C260.87 (17)S1—C1—C6—C134.5 (3)
N1—S1—C1—C254.19 (17)C3—C2—C7—C958.8 (2)
C6—C1—C2—C33.1 (3)C1—C2—C7—C9120.2 (2)
S1—C1—C2—C3178.13 (14)C3—C2—C7—C865.6 (2)
C6—C1—C2—C7175.89 (18)C1—C2—C7—C8115.4 (2)
S1—C1—C2—C72.9 (3)C5—C4—C10—C1255.6 (3)
C1—C2—C3—C40.6 (3)C3—C4—C10—C12125.8 (2)
C7—C2—C3—C4178.50 (18)C5—C4—C10—C1168.7 (2)
C2—C3—C4—C51.9 (3)C3—C4—C10—C11110.0 (2)
C2—C3—C4—C10179.41 (18)C5—C6—C13—C1562.7 (3)
C3—C4—C5—C62.0 (3)C1—C6—C13—C15120.0 (3)
C10—C4—C5—C6179.30 (19)C5—C6—C13—C1460.9 (3)
C4—C5—C6—C10.4 (3)C1—C6—C13—C14116.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.84 (3)2.12 (3)2.947 (3)170 (3)
N1—H2N···O2ii0.84 (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.
 

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