Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006463/dn6023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006463/dn6023Isup2.hkl |
CCDC reference: 185803
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.046
- wR factor = 0.117
- Data-to-parameter ratio = 12.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 29.96 From the CIF: _reflns_number_total 4979 Count of symmetry unique reflns 4784 Completeness (_total/calc) 104.08% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 195 Fraction of Friedel pairs measured 0.041 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
Le N-(2-chloroethyl)-N',N'-dibenzylsulfamide est obtenu à la fin des trois réactions en chaîne suivantes: carbamoylation–sulfamoylation à partir de l'ICS: a une solution de 1.1 équivalents de dibenzylamine dans 100 ml de dichloromethane est ajoutée une solution de chlorosulfonylcarbamate préparée préalablement par addition de tertiobutanol à une solution de 1 équivalent d'isocyanate de chlorosulfonyle (ICS), la réaction s'effectue à 273 K, et le produit obtenu est le N-tertiobutyloxycarbonyl-N',N'-dibenzylsulfamide.
Chloroéthylation selon Mitsunobu (Mitsunobu, 1981; Hughes, 1992): a température ambiante et sous agitation magnétique, une solution de 1.1 équivalents d'azodicarboxylate de diéthyle est ajoutée à une solution de: 1.1 équivalent de chloroéthanol, 1.1 équivalents de triphénylphosphine dissoute dans du THF (tétrahydrofurane) et 1 équivalent de N-tertiobutyloxycarbonyl-N',N'-dibenzylsulfamide. La réaction donne le N-butyloxycarbonyl-N-(2-chloroethyl)-N',N'-dibenzylsulfamide moins polaire que le précuseur.
Déprotection (clivage du tertiobutyloxycarbonyle): le N-tertiobutyloxycarbonyl-N-(2-chloroethyl)-N',N'-dibenzylsulfamide additionné de dichlorométhane anhydre est placé sous agitation magnétique à 273 K. Une solution à 25% d'acide trifluoroacétique dans du dichloromethane anhydre est ajoutée goutte à goutte jusqu'à disparition de l'ester carbamique et l'apparition d'un composé plus polaire. Le solvant est évaporé sous pression réduite et le résidu est lavé plusieurs fois à l'éther diethylique anhydre puis recristallisé dans l'éthanol.
Les données ont été enregistrées dans le groupe ponctuel 2/m, or la résolution de la structure a montré que le groupe d'espace est le groupe non-centrosymmétrique. Malgré l'absence d'un nombre suffisant de paires de Friedel (195, 4%), la structure absolue a pu étre définie en réalisant l'affinement du paramétre de Flack (option: TWIN, BASF) dans les deux cas de figure conduisant á une valeur x de 0.14 (15) dans un cas et de 0.86 (15) lorsque l'on inverse la structure. Les atomes d'hydrogénes ont été introduits en position calculée excepté pour les atomes d'hydrogénes des groupements NH qui ont été affinés avec un paramétre de température isotrope général. Les distances NH ont été contraintes á une valeur de 0,87 Å.
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); data reduction: WinGX (Farrugia, 1999); 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); software used to prepare material for publication: WinGX.
C16H19ClN2O2S | F(000) = 1424 |
Mr = 338.84 | Dx = 1.368 Mg m−3 |
Monoclinic, Cc | Melting point: 323 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.269 (2) Å | Cell parameters from 25 reflections |
b = 11.376 (1) Å | θ = 10–15° |
c = 25.738 (3) Å | µ = 0.37 mm−1 |
β = 94.47 (2)° | T = 293 K |
V = 3289.5 (8) Å3 | Prism, colorless |
Z = 8 | 0.5 × 0.4 × 0.3 mm |
Enraf-Nonius MACH3 diffractometer | Rint = 0.068 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.6° |
Graphite monochromator | h = 0→15 |
θ/2θ scans | k = −15→0 |
4979 measured reflections | l = −36→36 |
4979 independent reflections | 3 standard reflections every 120 min |
2938 reflections with I > 2σ(I) | intensity decay: 0.1% |
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)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0283P)2 + 3.3532P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
4979 reflections | Δρmax = 0.28 e Å−3 |
405 parameters | Δρmin = −0.31 e Å−3 |
4 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.14 (15) |
C16H19ClN2O2S | V = 3289.5 (8) Å3 |
Mr = 338.84 | Z = 8 |
Monoclinic, Cc | Mo Kα radiation |
a = 11.269 (2) Å | µ = 0.37 mm−1 |
b = 11.376 (1) Å | T = 293 K |
c = 25.738 (3) Å | 0.5 × 0.4 × 0.3 mm |
β = 94.47 (2)° |
Enraf-Nonius MACH3 diffractometer | Rint = 0.068 |
4979 measured reflections | 3 standard reflections every 120 min |
4979 independent reflections | intensity decay: 0.1% |
2938 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | Δρmax = 0.28 e Å−3 |
S = 1.11 | Δρmin = −0.31 e Å−3 |
4979 reflections | Absolute structure: Flack (1983) |
405 parameters | Absolute structure parameter: 0.14 (15) |
4 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1A | 0.23342 (16) | 0.33224 (14) | 0.24878 (6) | 0.0647 (4) | |
C1A | 0.2251 (5) | 0.3768 (5) | 0.1827 (2) | 0.0543 (14) | |
H1A1 | 0.2540 | 0.4568 | 0.1805 | 0.065* | |
H1A2 | 0.2761 | 0.3267 | 0.1636 | 0.065* | |
C2A | 0.1003 (5) | 0.3702 (5) | 0.1581 (2) | 0.0485 (13) | |
H2A1 | 0.1022 | 0.3768 | 0.1206 | 0.058* | |
H2A2 | 0.0673 | 0.2939 | 0.1656 | 0.058* | |
N1A | 0.0212 (4) | 0.4624 (4) | 0.17637 (15) | 0.0431 (10) | |
S1A | −0.01384 (11) | 0.57325 (11) | 0.14085 (5) | 0.0402 (3) | |
O1A | 0.0908 (3) | 0.6319 (3) | 0.12710 (14) | 0.0517 (9) | |
O2A | −0.0970 (4) | 0.6378 (3) | 0.16879 (14) | 0.0570 (10) | |
N2A | −0.0748 (3) | 0.5186 (3) | 0.08611 (15) | 0.0371 (9) | |
C3A | −0.1906 (4) | 0.4609 (4) | 0.08979 (18) | 0.0408 (11) | |
H3A1 | −0.2535 | 0.5189 | 0.0848 | 0.049* | |
H3A2 | −0.1938 | 0.4276 | 0.1243 | 0.049* | |
C4A | −0.2112 (5) | 0.3643 (5) | 0.0493 (2) | 0.0468 (12) | |
C5A | −0.1308 (6) | 0.2746 (5) | 0.0461 (2) | 0.0600 (15) | |
H5A | −0.0616 | 0.2745 | 0.0683 | 0.072* | |
C6A | −0.1504 (6) | 0.1855 (6) | 0.0110 (3) | 0.0693 (19) | |
H6A | −0.0949 | 0.1254 | 0.0094 | 0.083* | |
C7A | −0.2535 (7) | 0.1848 (6) | −0.0224 (3) | 0.0718 (19) | |
H7A | −0.2670 | 0.1248 | −0.0466 | 0.086* | |
C8A | −0.3342 (6) | 0.2727 (6) | −0.0192 (2) | 0.0611 (16) | |
H8A | −0.4038 | 0.2725 | −0.0412 | 0.073* | |
C9A | −0.3128 (5) | 0.3631 (6) | 0.0169 (2) | 0.0549 (15) | |
H9A | −0.3684 | 0.4231 | 0.0189 | 0.066* | |
C10A | −0.0593 (4) | 0.5842 (4) | 0.03761 (18) | 0.0381 (11) | |
H10A | −0.0646 | 0.5291 | 0.0087 | 0.046* | |
H10B | 0.0201 | 0.6176 | 0.0399 | 0.046* | |
C11A | −0.1478 (4) | 0.6813 (4) | 0.02572 (17) | 0.0350 (10) | |
C12A | −0.2431 (5) | 0.6678 (5) | −0.0107 (2) | 0.0505 (13) | |
H12A | −0.2520 | 0.5975 | −0.0291 | 0.061* | |
C13A | −0.3261 (5) | 0.7570 (5) | −0.0207 (2) | 0.0589 (15) | |
H13A | −0.3902 | 0.7464 | −0.0452 | 0.071* | |
C14A | −0.3121 (6) | 0.8610 (6) | 0.0061 (2) | 0.0612 (17) | |
H14A | −0.3677 | 0.9208 | 0.0000 | 0.073* | |
C15A | −0.2180 (6) | 0.8775 (5) | 0.0416 (2) | 0.0583 (15) | |
H15A | −0.2093 | 0.9485 | 0.0593 | 0.070* | |
C16A | −0.1345 (5) | 0.7888 (5) | 0.0515 (2) | 0.0485 (13) | |
H16A | −0.0696 | 0.8013 | 0.0754 | 0.058* | |
Cl1B | 0.01908 (15) | 1.02453 (15) | 0.12883 (6) | 0.0635 (4) | |
C1B | 0.0755 (5) | 1.0264 (5) | 0.1952 (2) | 0.0493 (13) | |
H1B1 | 0.1566 | 1.0556 | 0.1976 | 0.059* | |
H1B2 | 0.0281 | 1.0798 | 0.2145 | 0.059* | |
C2B | 0.0737 (5) | 0.9066 (5) | 0.2196 (2) | 0.0502 (13) | |
H2B1 | 0.0870 | 0.9146 | 0.2571 | 0.060* | |
H2B2 | −0.0046 | 0.8723 | 0.2120 | 0.060* | |
N1B | 0.1629 (4) | 0.8269 (4) | 0.20116 (15) | 0.0412 (10) | |
S1B | 0.28085 (11) | 0.79625 (11) | 0.23717 (5) | 0.0390 (3) | |
O1B | 0.3419 (3) | 0.7093 (3) | 0.20943 (14) | 0.0541 (10) | |
O2B | 0.3424 (3) | 0.9026 (3) | 0.25142 (14) | 0.0549 (10) | |
N2B | 0.2339 (3) | 0.7461 (3) | 0.29128 (14) | 0.0352 (8) | |
C3B | 0.3078 (4) | 0.7661 (4) | 0.34059 (18) | 0.0388 (11) | |
H3B1 | 0.2565 | 0.7637 | 0.3691 | 0.047* | |
H3B2 | 0.3414 | 0.8445 | 0.3397 | 0.047* | |
C4B | 0.4079 (4) | 0.6799 (4) | 0.35196 (18) | 0.0390 (11) | |
C5B | 0.3987 (5) | 0.5924 (5) | 0.3878 (2) | 0.0576 (15) | |
H5B | 0.3309 | 0.5877 | 0.4061 | 0.069* | |
C6B | 0.4892 (6) | 0.5100 (6) | 0.3973 (3) | 0.0725 (19) | |
H6B | 0.4813 | 0.4502 | 0.4214 | 0.087* | |
C7B | 0.5894 (6) | 0.5175 (6) | 0.3710 (3) | 0.0636 (18) | |
H7B | 0.6500 | 0.4627 | 0.3775 | 0.076* | |
C8B | 0.6018 (5) | 0.6048 (6) | 0.3353 (2) | 0.0578 (15) | |
H8B | 0.6702 | 0.6091 | 0.3174 | 0.069* | |
C9B | 0.5113 (4) | 0.6871 (5) | 0.3259 (2) | 0.0448 (12) | |
H9B | 0.5200 | 0.7474 | 0.3021 | 0.054* | |
C10B | 0.1737 (4) | 0.6306 (4) | 0.28696 (19) | 0.0425 (11) | |
H10C | 0.2327 | 0.5686 | 0.2919 | 0.051* | |
H10D | 0.1344 | 0.6222 | 0.2523 | 0.051* | |
C11B | 0.0832 (4) | 0.6167 (5) | 0.32659 (19) | 0.0411 (11) | |
C12B | 0.0830 (5) | 0.5169 (5) | 0.3576 (2) | 0.0489 (13) | |
H12B | 0.1400 | 0.4590 | 0.3541 | 0.059* | |
C13B | −0.0006 (6) | 0.5023 (6) | 0.3936 (2) | 0.0568 (15) | |
H13B | 0.0001 | 0.4350 | 0.4141 | 0.068* | |
C14B | −0.0859 (5) | 0.5892 (6) | 0.3989 (2) | 0.0559 (15) | |
H14B | −0.1430 | 0.5798 | 0.4228 | 0.067* | |
C15B | −0.0853 (5) | 0.6884 (6) | 0.3689 (2) | 0.0597 (16) | |
H15B | −0.1413 | 0.7471 | 0.3729 | 0.072* | |
C16B | −0.0021 (5) | 0.7018 (5) | 0.3327 (2) | 0.0547 (14) | |
H16B | −0.0035 | 0.7690 | 0.3121 | 0.066* | |
H1A | −0.023 (4) | 0.450 (5) | 0.2012 (16) | 0.059 (12)* | |
H1B | 0.141 (5) | 0.778 (4) | 0.1766 (16) | 0.059 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0735 (10) | 0.0631 (9) | 0.0561 (9) | 0.0214 (8) | −0.0042 (8) | 0.0042 (7) |
C1A | 0.046 (3) | 0.057 (3) | 0.061 (3) | 0.012 (3) | 0.010 (3) | 0.010 (3) |
C2A | 0.056 (3) | 0.044 (3) | 0.045 (3) | 0.017 (3) | 0.003 (2) | −0.003 (2) |
N1A | 0.042 (2) | 0.050 (2) | 0.037 (2) | 0.015 (2) | 0.0061 (18) | 0.0077 (19) |
S1A | 0.0445 (7) | 0.0363 (6) | 0.0391 (6) | 0.0036 (6) | −0.0014 (5) | −0.0015 (5) |
O1A | 0.050 (2) | 0.046 (2) | 0.057 (2) | −0.0215 (18) | −0.0048 (18) | 0.0047 (18) |
O2A | 0.072 (3) | 0.049 (2) | 0.050 (2) | 0.026 (2) | 0.0024 (19) | −0.0094 (18) |
N2A | 0.035 (2) | 0.039 (2) | 0.037 (2) | 0.0033 (17) | 0.0009 (17) | 0.0048 (17) |
C3A | 0.037 (2) | 0.047 (3) | 0.040 (2) | −0.005 (2) | 0.008 (2) | −0.004 (2) |
C4A | 0.045 (3) | 0.044 (3) | 0.051 (3) | −0.007 (2) | −0.002 (2) | 0.003 (2) |
C5A | 0.062 (4) | 0.047 (3) | 0.069 (4) | −0.006 (3) | −0.010 (3) | −0.006 (3) |
C6A | 0.082 (5) | 0.053 (4) | 0.071 (4) | −0.003 (3) | −0.004 (4) | −0.003 (3) |
C7A | 0.093 (5) | 0.064 (4) | 0.057 (4) | −0.018 (4) | −0.002 (4) | −0.004 (3) |
C8A | 0.061 (4) | 0.060 (4) | 0.060 (4) | −0.027 (3) | −0.011 (3) | 0.007 (3) |
C9A | 0.045 (3) | 0.059 (4) | 0.060 (3) | −0.008 (3) | 0.000 (3) | 0.007 (3) |
C10A | 0.045 (3) | 0.037 (3) | 0.033 (2) | −0.002 (2) | 0.002 (2) | 0.002 (2) |
C11A | 0.039 (3) | 0.034 (2) | 0.032 (2) | 0.003 (2) | 0.002 (2) | 0.0071 (19) |
C12A | 0.052 (3) | 0.047 (3) | 0.051 (3) | 0.004 (3) | −0.006 (3) | −0.001 (2) |
C13A | 0.049 (3) | 0.064 (4) | 0.062 (4) | 0.010 (3) | −0.011 (3) | 0.007 (3) |
C14A | 0.056 (4) | 0.063 (4) | 0.065 (4) | 0.029 (3) | 0.011 (3) | 0.020 (3) |
C15A | 0.072 (4) | 0.040 (3) | 0.063 (4) | 0.020 (3) | 0.009 (3) | −0.001 (3) |
C16A | 0.056 (3) | 0.042 (3) | 0.046 (3) | 0.000 (3) | −0.003 (2) | −0.005 (2) |
Cl1B | 0.0606 (9) | 0.0764 (11) | 0.0524 (8) | 0.0198 (8) | −0.0025 (7) | 0.0080 (8) |
C1B | 0.050 (3) | 0.047 (3) | 0.050 (3) | 0.014 (3) | −0.004 (3) | −0.004 (2) |
C2B | 0.043 (3) | 0.056 (3) | 0.052 (3) | 0.008 (3) | 0.006 (2) | 0.008 (3) |
N1B | 0.038 (2) | 0.047 (3) | 0.038 (2) | 0.011 (2) | 0.0016 (18) | −0.0015 (19) |
S1B | 0.0324 (6) | 0.0430 (7) | 0.0415 (6) | 0.0028 (6) | 0.0033 (5) | 0.0025 (6) |
O1B | 0.051 (2) | 0.066 (3) | 0.047 (2) | 0.023 (2) | 0.0144 (17) | 0.0010 (18) |
O2B | 0.048 (2) | 0.056 (2) | 0.060 (2) | −0.0183 (18) | 0.0010 (18) | 0.0111 (19) |
N2B | 0.036 (2) | 0.036 (2) | 0.0339 (19) | −0.0055 (17) | 0.0032 (16) | 0.0048 (16) |
C3B | 0.033 (2) | 0.045 (3) | 0.038 (3) | 0.009 (2) | 0.000 (2) | −0.003 (2) |
C4B | 0.035 (2) | 0.042 (3) | 0.038 (3) | −0.001 (2) | −0.004 (2) | −0.003 (2) |
C5B | 0.045 (3) | 0.068 (4) | 0.060 (3) | 0.005 (3) | 0.002 (3) | 0.022 (3) |
C6B | 0.065 (4) | 0.059 (4) | 0.092 (5) | 0.012 (3) | −0.004 (4) | 0.029 (4) |
C7B | 0.058 (4) | 0.055 (4) | 0.074 (4) | 0.021 (3) | −0.019 (3) | −0.004 (3) |
C8B | 0.038 (3) | 0.077 (4) | 0.058 (3) | 0.013 (3) | 0.001 (3) | −0.009 (3) |
C9B | 0.042 (3) | 0.051 (3) | 0.042 (3) | 0.006 (2) | −0.001 (2) | 0.005 (2) |
C10B | 0.043 (3) | 0.037 (3) | 0.047 (3) | −0.009 (2) | 0.000 (2) | −0.002 (2) |
C11B | 0.039 (3) | 0.042 (3) | 0.041 (3) | −0.006 (2) | −0.002 (2) | 0.003 (2) |
C12B | 0.051 (3) | 0.037 (3) | 0.058 (3) | −0.004 (2) | −0.001 (3) | 0.009 (2) |
C13B | 0.068 (4) | 0.051 (3) | 0.050 (3) | −0.020 (3) | −0.003 (3) | 0.011 (3) |
C14B | 0.045 (3) | 0.071 (4) | 0.052 (3) | −0.022 (3) | 0.005 (3) | 0.009 (3) |
C15B | 0.040 (3) | 0.065 (4) | 0.075 (4) | −0.002 (3) | 0.012 (3) | 0.015 (3) |
C16B | 0.045 (3) | 0.057 (4) | 0.063 (3) | −0.005 (3) | 0.005 (3) | 0.018 (3) |
Cl1A—C1A | 1.771 (6) | Cl1B—C1B | 1.776 (5) |
C1A—C2A | 1.498 (7) | C1B—C2B | 1.501 (7) |
C1A—H1A1 | 0.9700 | C1B—H1B1 | 0.9700 |
C1A—H1A2 | 0.9700 | C1B—H1B2 | 0.9700 |
C2A—N1A | 1.476 (6) | C2B—N1B | 1.460 (6) |
C2A—H2A1 | 0.9700 | C2B—H2B1 | 0.9700 |
C2A—H2A2 | 0.9700 | C2B—H2B2 | 0.9700 |
N1A—S1A | 1.589 (4) | N1B—S1B | 1.598 (4) |
N1A—H1A | 0.86 (2) | N1B—H1B | 0.87 (2) |
S1A—O1A | 1.423 (4) | S1B—O1B | 1.427 (4) |
S1A—O2A | 1.428 (4) | S1B—O2B | 1.428 (4) |
S1A—N2A | 1.641 (4) | S1B—N2B | 1.631 (4) |
N2A—C3A | 1.470 (6) | N2B—C10B | 1.479 (6) |
N2A—C10A | 1.476 (6) | N2B—C3B | 1.480 (6) |
C3A—C4A | 1.519 (7) | C3B—C4B | 1.506 (7) |
C3A—H3A1 | 0.9700 | C3B—H3B1 | 0.9700 |
C3A—H3A2 | 0.9700 | C3B—H3B2 | 0.9700 |
C4A—C9A | 1.364 (7) | C4B—C5B | 1.366 (7) |
C4A—C5A | 1.370 (8) | C4B—C9B | 1.392 (7) |
C5A—C6A | 1.365 (8) | C5B—C6B | 1.393 (8) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—C7A | 1.389 (9) | C6B—C7B | 1.363 (9) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—C8A | 1.358 (9) | C7B—C8B | 1.368 (9) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.396 (8) | C8B—C9B | 1.392 (7) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—H9A | 0.9300 | C9B—H9B | 0.9300 |
C10A—C11A | 1.505 (6) | C10B—C11B | 1.506 (7) |
C10A—H10A | 0.9700 | C10B—H10C | 0.9700 |
C10A—H10B | 0.9700 | C10B—H10D | 0.9700 |
C11A—C12A | 1.378 (7) | C11B—C16B | 1.381 (7) |
C11A—C16A | 1.393 (7) | C11B—C12B | 1.388 (7) |
C12A—C13A | 1.391 (8) | C12B—C13B | 1.381 (8) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C14A | 1.373 (9) | C13B—C14B | 1.393 (9) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.356 (8) | C14B—C15B | 1.368 (8) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.389 (7) | C15B—C16B | 1.382 (8) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C2A—C1A—Cl1A | 111.6 (4) | C2B—C1B—Cl1B | 112.0 (4) |
C2A—C1A—H1A1 | 109.3 | C2B—C1B—H1B1 | 109.2 |
Cl1A—C1A—H1A1 | 109.3 | Cl1B—C1B—H1B1 | 109.2 |
C2A—C1A—H1A2 | 109.3 | C2B—C1B—H1B2 | 109.2 |
Cl1A—C1A—H1A2 | 109.3 | Cl1B—C1B—H1B2 | 109.2 |
H1A1—C1A—H1A2 | 108.0 | H1B1—C1B—H1B2 | 107.9 |
N1A—C2A—C1A | 113.7 (4) | N1B—C2B—C1B | 113.4 (4) |
N1A—C2A—H2A1 | 108.8 | N1B—C2B—H2B1 | 108.9 |
C1A—C2A—H2A1 | 108.8 | C1B—C2B—H2B1 | 108.9 |
N1A—C2A—H2A2 | 108.8 | N1B—C2B—H2B2 | 108.9 |
C1A—C2A—H2A2 | 108.8 | C1B—C2B—H2B2 | 108.9 |
H2A1—C2A—H2A2 | 107.7 | H2B1—C2B—H2B2 | 107.7 |
C2A—N1A—S1A | 120.6 (3) | C2B—N1B—S1B | 120.7 (3) |
C2A—N1A—H1A | 121 (4) | C2B—N1B—H1B | 118 (4) |
S1A—N1A—H1A | 116 (4) | S1B—N1B—H1B | 118 (4) |
O1A—S1A—O2A | 118.2 (2) | O1B—S1B—O2B | 118.2 (2) |
O1A—S1A—N1A | 110.0 (2) | O1B—S1B—N1B | 105.8 (2) |
O2A—S1A—N1A | 105.2 (2) | O2B—S1B—N1B | 109.2 (2) |
O1A—S1A—N2A | 105.3 (2) | O1B—S1B—N2B | 112.7 (2) |
O2A—S1A—N2A | 112.3 (2) | O2B—S1B—N2B | 105.1 (2) |
N1A—S1A—N2A | 105.2 (2) | N1B—S1B—N2B | 105.1 (2) |
C3A—N2A—C10A | 116.4 (4) | C10B—N2B—C3B | 115.2 (4) |
C3A—N2A—S1A | 115.3 (3) | C10B—N2B—S1B | 115.1 (3) |
C10A—N2A—S1A | 117.7 (3) | C3B—N2B—S1B | 118.7 (3) |
N2A—C3A—C4A | 111.6 (4) | N2B—C3B—C4B | 115.4 (4) |
N2A—C3A—H3A1 | 109.3 | N2B—C3B—H3B1 | 108.4 |
C4A—C3A—H3A1 | 109.3 | C4B—C3B—H3B1 | 108.4 |
N2A—C3A—H3A2 | 109.3 | N2B—C3B—H3B2 | 108.4 |
C4A—C3A—H3A2 | 109.3 | C4B—C3B—H3B2 | 108.4 |
H3A1—C3A—H3A2 | 108.0 | H3B1—C3B—H3B2 | 107.5 |
C9A—C4A—C5A | 118.9 (5) | C5B—C4B—C9B | 118.6 (5) |
C9A—C4A—C3A | 120.1 (5) | C5B—C4B—C3B | 120.7 (5) |
C5A—C4A—C3A | 120.9 (5) | C9B—C4B—C3B | 120.7 (4) |
C6A—C5A—C4A | 121.3 (6) | C4B—C5B—C6B | 121.1 (6) |
C6A—C5A—H5A | 119.4 | C4B—C5B—H5B | 119.5 |
C4A—C5A—H5A | 119.4 | C6B—C5B—H5B | 119.5 |
C5A—C6A—C7A | 119.9 (7) | C7B—C6B—C5B | 119.6 (6) |
C5A—C6A—H6A | 120.1 | C7B—C6B—H6B | 120.2 |
C7A—C6A—H6A | 120.1 | C5B—C6B—H6B | 120.2 |
C8A—C7A—C6A | 119.4 (6) | C6B—C7B—C8B | 120.7 (6) |
C8A—C7A—H7A | 120.3 | C6B—C7B—H7B | 119.6 |
C6A—C7A—H7A | 120.3 | C8B—C7B—H7B | 119.6 |
C7A—C8A—C9A | 120.0 (6) | C7B—C8B—C9B | 119.6 (6) |
C7A—C8A—H8A | 120.0 | C7B—C8B—H8B | 120.2 |
C9A—C8A—H8A | 120.0 | C9B—C8B—H8B | 120.2 |
C4A—C9A—C8A | 120.5 (6) | C4B—C9B—C8B | 120.4 (5) |
C4A—C9A—H9A | 119.7 | C4B—C9B—H9B | 119.8 |
C8A—C9A—H9A | 119.7 | C8B—C9B—H9B | 119.8 |
N2A—C10A—C11A | 115.0 (4) | N2B—C10B—C11B | 111.9 (4) |
N2A—C10A—H10A | 108.5 | N2B—C10B—H10C | 109.2 |
C11A—C10A—H10A | 108.5 | C11B—C10B—H10C | 109.2 |
N2A—C10A—H10B | 108.5 | N2B—C10B—H10D | 109.2 |
C11A—C10A—H10B | 108.5 | C11B—C10B—H10D | 109.2 |
H10A—C10A—H10B | 107.5 | H10C—C10B—H10D | 107.9 |
C12A—C11A—C16A | 118.1 (5) | C16B—C11B—C12B | 118.4 (5) |
C12A—C11A—C10A | 121.7 (5) | C16B—C11B—C10B | 121.1 (5) |
C16A—C11A—C10A | 120.2 (4) | C12B—C11B—C10B | 120.4 (5) |
C11A—C12A—C13A | 121.4 (5) | C13B—C12B—C11B | 121.0 (5) |
C11A—C12A—H12A | 119.3 | C13B—C12B—H12B | 119.5 |
C13A—C12A—H12A | 119.3 | C11B—C12B—H12B | 119.5 |
C14A—C13A—C12A | 119.2 (6) | C12B—C13B—C14B | 119.6 (5) |
C14A—C13A—H13A | 120.4 | C12B—C13B—H13B | 120.2 |
C12A—C13A—H13A | 120.4 | C14B—C13B—H13B | 120.2 |
C15A—C14A—C13A | 120.7 (5) | C15B—C14B—C13B | 119.7 (5) |
C15A—C14A—H14A | 119.7 | C15B—C14B—H14B | 120.2 |
C13A—C14A—H14A | 119.7 | C13B—C14B—H14B | 120.2 |
C14A—C15A—C16A | 120.4 (6) | C14B—C15B—C16B | 120.4 (6) |
C14A—C15A—H15A | 119.8 | C14B—C15B—H15B | 119.8 |
C16A—C15A—H15A | 119.8 | C16B—C15B—H15B | 119.8 |
C15A—C16A—C11A | 120.3 (5) | C11B—C16B—C15B | 120.9 (5) |
C15A—C16A—H16A | 119.9 | C11B—C16B—H16B | 119.5 |
C11A—C16A—H16A | 119.9 | C15B—C16B—H16B | 119.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B···O1A | 0.87 (2) | 2.14 (4) | 2.995 (6) | 169 (5) |
N1A—H1A···O2Bi | 0.86 (2) | 2.13 (5) | 2.977 (5) | 169 (5) |
Symmetry code: (i) x−1/2, y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C16H19ClN2O2S |
Mr | 338.84 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 11.269 (2), 11.376 (1), 25.738 (3) |
β (°) | 94.47 (2) |
V (Å3) | 3289.5 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.5 × 0.4 × 0.3 |
Data collection | |
Diffractometer | Enraf-Nonius MACH3 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4979, 4979, 2938 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.117, 1.11 |
No. of reflections | 4979 |
No. of parameters | 405 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.31 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.14 (15) |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), WinGX (Farrugia, 1999), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX.
D—H···A | D—H | H···A | D···A | D—H···A |
N1B—H1B···O1A | 0.87 (2) | 2.14 (4) | 2.995 (6) | 169 (5) |
N1A—H1A···O2Bi | 0.86 (2) | 2.13 (5) | 2.977 (5) | 169 (5) |
Symmetry code: (i) x−1/2, y−1/2, z. |
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Les N-(2-chloroéthyl) nitrosourées (CENU) appartiennent α une famille d'agents alkylants (Rajski et al., 1998), dont la cible est le matériel génétique même de la cellule transformée. Ces agents comptent parmi les plus efficaces mais sont ceux aussi dont les limites d'utilization sont les plus sévères en raison de leurs effets secondaires (Montero et al., 1984; Sosnovsky, 1990; McCormick et al., 1990; Dulude, 1995; Lown, 1981). Les N-(2-chloroéthyl)nitrososulfamides (CENS) (Dewynter et al., 1992; Abdaoui et al., 1996; Abdaoui et al., 1996; Abdaoui et al., 1996; Dewynter et al., 1996; Abdaoui et al., 2000) sont apparentés aux nitrosourées (Gnewuck et al., 1997), mais ne présentent pas, par nature, l'activité carbamoylante de ces dernières, tenue en partie responsable de leur importante toxicité. La synthèse s'articule autour de l'aménagement polyfonctionnel de l'isocyanate de chlorosulfonyle (ICS) et comporte quatre réactions en chaîne conduisant au produit final le CENS. Le composé N-(2-chloroethyl)-N',N'-dibenzylsulfamide, objet de cette étude structurale, est un produit intermédiaire dérivant de la troisième réaction. L'unité asymétrique est formée de deux molécules identiques maintenues par des liaisons hydrogéne. Les plans des cycles phényle font un angle dièdre moyen de 12.33°,les distances C—C dans les cycles phényle varient autour des valeurs moyennes suivantes: 1.377 (7) e t 1.381 (8) Å. On note une dissymétrie des liaisons S—N du motif sulfamide: S—N1 = 1.594 (3) Å e t S—N2 = 1.636 (4) Å (Abdaoui et al., 2000). L'empilement moléculaire dans le cristal est assurée par un réseau de liaisons hydrogénes qui se développe sous forme de chaines paralléles aux diagonales du plan ab (Fig. 2).